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Showing metabocard for Vincristine (HMDB0014681)

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enzymes (5)transporters (7) Show 12 proteins
Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:50 UTC
Update Date2022-03-07 02:51:42 UTC
HMDB IDHMDB0014681
Secondary Accession Numbers
  • HMDB14681
Metabolite Identification
Common NameVincristine
DescriptionVincristine is only found in individuals that have used or taken this drug. It is an antitumor alkaloid isolated from Vinca Rosea. (Merck, 11th ed.)The antitumor activity of Vincristine is thought to be due primarily to inhibition of mitosis at metaphase through its interaction with tubulin. Like other vinca alkaloids, Vincristine may also interfere with: 1) amino acid, cyclic AMP, and glutathione metabolism, 2) calmodulin-dependent Ca2+-transport ATPase activity, 3) cellular respiration, and 4) nucleic acid and lipid biosynthesis.
Structure
Data?1582753207
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0014681 (Vincristine)

541
  Mrv0541 02231214452D          

 63 71  0  0  1  0            999 V2000
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M  END
Download

3D MOL for HMDB0014681 (Vincristine)

HMDB0014681
     RDKit          3D
Vincristine
116124  0  0  0  0  0  0  0  0999 V2000
   -8.3659    2.8640   -1.4772 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3966    1.8927   -2.0828 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1285    1.8261   -1.2495 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.6159    3.1456   -1.2626 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1522    0.9597   -2.0168 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1341    0.5182   -0.9785 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.9294   -0.3047    0.0096 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4978    0.6679    0.8722 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8668    1.1811    1.9645 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3476    1.2829    2.0221 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6996   -0.0063    1.7678 C   0  0  0  0  0  0  0  0  0  0  0  0
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    3.5178    0.3486    0.0712 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6392    3.3043    1.1228 H   0  0  0  0  0  0  0  0  0  0  0  0
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    5.7844    4.2104   -0.1376 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3157   -0.6219    3.6446 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8261    0.6296    2.5151 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7464    0.9071    2.9102 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -7.4126    0.9155    0.1705 H   0  0  0  0  0  0  0  0  0  0  0  0
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 58112  1  1
 59113  1  0
 59114  1  0
 60115  1  0
 60116  1  0
M  END
Download

3D SDF for HMDB0014681 (Vincristine)

541
  Mrv0541 02231214452D          

 63 71  0  0  1  0            999 V2000
    5.6185   -3.9523    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.6643   -2.3396    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.2773   -2.8916    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1059   -3.6986    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.5551   -1.5851    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.7488    1.3650    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.6806   -4.9083    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3863    0.2818    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3263    0.3189    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.9718    3.8932    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6167   -2.1136    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.1573   -1.2880    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.6815    4.0205    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.8513    1.4175    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
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    5.9191   -0.5546    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    3.3390   -3.4201    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    4.9264    0.3392    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3122   -4.4050    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4350    0.0185    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9420   -1.0331    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4424    0.9122    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    5.9721    1.9518    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4225    2.0059    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4094    2.6514    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.8784    0.9320    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3215   -5.3500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8905   -3.4436    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1315    3.0816    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2945    3.4685    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0352    2.7344    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1472    3.9219    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.4418    4.3787    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2068    3.5414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8569    4.0493    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2279    2.5899    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5558    1.1934    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1145    1.7776    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    2.3277    1.4447    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    6.7591    3.2112    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
 21  1  1  6  0  0  0
  1 37  1  0  0  0  0
 19  2  1  6  0  0  0
  3 29  1  0  0  0  0
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  4 29  2  0  0  0  0
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  8 41  1  0  0  0  0
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 47 10  1  1  0  0  0
 11 16  1  0  0  0  0
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 16 61  1  1  0  0  0
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 59 60  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0014681

> <DATABASE_NAME>
hmdb

> <SMILES>
[H][C@@]12N3CC[C@@]11C4=CC(=C(OC)C=C4N(C=O)[C@@]1([H])[C@](O)([C@H](OC(C)=O)[C@]2(CC)C=CC3)C(=O)OC)[C@]1(C[C@]2([H])CN(C[C@](O)(CC)C2)CCC2=C1NC1=CC=CC=C21)C(=O)OC

> <INCHI_IDENTIFIER>
InChI=1S/C46H56N4O10/c1-7-42(55)22-28-23-45(40(53)58-5,36-30(14-18-48(24-28)25-42)29-12-9-10-13-33(29)47-36)32-20-31-34(21-35(32)57-4)50(26-51)38-44(31)16-19-49-17-11-15-43(8-2,37(44)49)39(60-27(3)52)46(38,56)41(54)59-6/h9-13,15,20-21,26,28,37-39,47,55-56H,7-8,14,16-19,22-25H2,1-6H3/t28-,37+,38-,39-,42+,43-,44-,45+,46+/m1/s1

> <INCHI_KEY>
OGWKCGZFUXNPDA-XQKSVPLYSA-N

> <FORMULA>
C46H56N4O10

> <MOLECULAR_WEIGHT>
824.9576

> <EXACT_MASS>
824.399644032

> <JCHEM_ACCEPTOR_COUNT>
9

> <JCHEM_AVERAGE_POLARIZABILITY>
88.58705315627984

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
methyl (1R,9R,10S,11R,12R,19R)-11-(acetyloxy)-12-ethyl-4-[(13S,15S,17S)-17-ethyl-17-hydroxy-13-(methoxycarbonyl)-1,11-diazatetracyclo[13.3.1.0⁴,¹².0⁵,¹⁰]nonadeca-4(12),5,7,9-tetraen-13-yl]-8-formyl-10-hydroxy-5-methoxy-8,16-diazapentacyclo[10.6.1.0¹,⁹.0²,⁷.0¹⁶,¹⁹]nonadeca-2,4,6,13-tetraene-10-carboxylate

> <ALOGPS_LOGP>
3.36

> <JCHEM_LOGP>
3.128179157333334

> <ALOGPS_LOGS>
-4.44

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
9

> <JCHEM_PHYSIOLOGICAL_CHARGE>
2

> <JCHEM_PKA>
14.405141780055722

> <JCHEM_PKA_STRONGEST_ACIDIC>
10.849017536198744

> <JCHEM_PKA_STRONGEST_BASIC>
8.662524172947244

> <JCHEM_POLAR_SURFACE_AREA>
171.17000000000002

> <JCHEM_REFRACTIVITY>
221.48039999999995

> <JCHEM_ROTATABLE_BOND_COUNT>
10

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
3.00e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
vincristine

> <JCHEM_VEBER_RULE>
0

$$$$
Download

3D-SDF for HMDB0014681 (Vincristine)

HMDB0014681
     RDKit          3D
Vincristine
116124  0  0  0  0  0  0  0  0999 V2000
   -8.3659    2.8640   -1.4772 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3966    1.8927   -2.0828 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1285    1.8261   -1.2495 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.6159    3.1456   -1.2626 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1522    0.9597   -2.0168 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1341    0.5182   -0.9785 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.9294   -0.3047    0.0096 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4978    0.6679    0.8722 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8668    1.1811    1.9645 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3476    1.2829    2.0221 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6996   -0.0063    1.7678 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0970   -0.5335    0.6906 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7875   -1.8323    0.9587 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1643   -2.1771    2.1949 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0735   -3.3527    2.9337 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5558   -3.4259    4.2189 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1369   -2.3108    4.7756 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2118   -1.1636    4.0202 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7330   -1.0619    2.7201 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7956    0.0468   -0.6559 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.5082    1.5248   -0.5686 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8440    1.9327    0.3889 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9619    2.3865   -1.5132 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6462    3.7770   -1.3603 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4423   -0.3746   -1.1717 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4561   -1.0513   -0.3858 C   0  0  0  0  0  0  0  0  0  0  0  0
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M  END
Download

PDB for HMDB0014681 (Vincristine)

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 541                                               
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  O   UNK     0      10.488  -7.378   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0      12.440  -4.367   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0      13.584  -5.398   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0      13.264  -6.904   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0      14.103  -2.959   0.000  0.00  0.00           O+0
HETATM    6  O   UNK     0      12.598   2.548   0.000  0.00  0.00           O+0
HETATM    7  O   UNK     0      12.470  -9.162   0.000  0.00  0.00           O+0
HETATM    8  O   UNK     0      10.054   0.526   0.000  0.00  0.00           O+0
HETATM    9  O   UNK     0       8.076   0.595   0.000  0.00  0.00           O+0
HETATM   10  O   UNK     0      14.881   7.267   0.000  0.00  0.00           O+0
HETATM   11  N   UNK     0       6.751  -3.945   0.000  0.00  0.00           N+0
HETATM   12  N   UNK     0      11.494  -2.404   0.000  0.00  0.00           N+0
HETATM   13  N   UNK     0      10.605   7.505   0.000  0.00  0.00           N+0
HETATM   14  N   UNK     0       7.189   2.646   0.000  0.00  0.00           N+0
HETATM   15  C   UNK     0       9.122  -3.175   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       8.159  -4.244   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       8.604  -5.614   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      10.530  -3.474   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      10.975  -4.843   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       8.529  -1.580   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      10.012  -5.913   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       9.641  -0.736   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       6.306  -2.576   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       9.080  -7.078   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       7.641  -6.683   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      11.049  -1.035   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       5.788  -5.015   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       6.233  -6.384   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      12.120  -5.874   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       9.196   0.633   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       8.049  -8.223   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      12.012   0.035   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      12.958  -1.928   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      10.159   1.703   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      11.567   1.404   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0       9.683   3.168   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0      10.964  -8.842   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0      11.148   3.643   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0       8.255   3.744   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0      11.964   4.949   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0       9.106   1.740   0.000  0.00  0.00           C+0
HETATM   42  C   UNK     0       9.933  -9.987   0.000  0.00  0.00           C+0
HETATM   43  C   UNK     0      14.729  -6.428   0.000  0.00  0.00           C+0
HETATM   44  C   UNK     0      13.312   5.752   0.000  0.00  0.00           C+0
HETATM   45  C   UNK     0      11.750   6.475   0.000  0.00  0.00           C+0
HETATM   46  C   UNK     0       7.532   5.104   0.000  0.00  0.00           C+0
HETATM   47  C   UNK     0      13.341   7.321   0.000  0.00  0.00           C+0
HETATM   48  C   UNK     0      12.025   8.174   0.000  0.00  0.00           C+0
HETATM   49  C   UNK     0       7.853   6.611   0.000  0.00  0.00           C+0
HETATM   50  C   UNK     0       9.066   7.559   0.000  0.00  0.00           C+0
HETATM   51  C   UNK     0       6.025   4.834   0.000  0.00  0.00           C+0
HETATM   52  C   UNK     0      14.104   2.228   0.000  0.00  0.00           C+0
HETATM   53  C   UNK     0       5.814   3.318   0.000  0.00  0.00           C+0
HETATM   54  C   UNK     0      14.158   8.627   0.000  0.00  0.00           C+0
HETATM   55  C   UNK     0       4.783   5.834   0.000  0.00  0.00           C+0
HETATM   56  C   UNK     0       4.345   2.697   0.000  0.00  0.00           C+0
HETATM   57  C   UNK     0      13.435   9.987   0.000  0.00  0.00           C+0
HETATM   58  C   UNK     0      11.809   0.773   0.000  0.00  0.00           C+0
HETATM   59  C   UNK     0       3.301   5.247   0.000  0.00  0.00           C+0
HETATM   60  C   UNK     0       3.080   3.668   0.000  0.00  0.00           C+0
HETATM   61  H   UNK     0       7.778  -3.073   0.000  0.00  0.00           H+0
HETATM   62  H   UNK     0      11.736  -3.730   0.000  0.00  0.00           H+0
HETATM   63  H   UNK     0      12.617   5.994   0.000  0.00  0.00           H+0
CONECT    1   21   37                                                       
CONECT    2   19                                                            
CONECT    3   29   43                                                       
CONECT    4   29                                                            
CONECT    5   33                                                            
CONECT    6   35   52                                                       
CONECT    7   37                                                            
CONECT    8   41   58                                                       
CONECT    9   41                                                            
CONECT   10   47                                                            
CONECT   11   16   23   27                                                  
CONECT   12   18   26   33                                                  
CONECT   13   45   48   50                                                  
CONECT   14   39   53                                                       
CONECT   15   16   18   20   22                                             
CONECT   16   11   15   17   61                                             
CONECT   17   16   21   24   25                                             
CONECT   18   12   15   19   62                                             
CONECT   19    2   18   21   29                                             
CONECT   20   15   23                                                       
CONECT   21    1   17   19                                                  
CONECT   22   15   26   30                                                  
CONECT   23   11   20                                                       
CONECT   24   17   31                                                       
CONECT   25   17   28                                                       
CONECT   26   12   22   32                                                  
CONECT   27   11   28                                                       
CONECT   28   25   27                                                       
CONECT   29    3    4   19                                                  
CONECT   30   22   34                                                       
CONECT   31   24                                                            
CONECT   32   26   35                                                       
CONECT   33    5   12                                                       
CONECT   34   30   35   36                                                  
CONECT   35    6   32   34                                                  
CONECT   36   34   38   39   41                                             
CONECT   37    1    7   42                                                  
CONECT   38   36   40                                                       
CONECT   39   14   36   46                                                  
CONECT   40   38   44   45   63                                             
CONECT   41    8    9   36                                                  
CONECT   42   37                                                            
CONECT   43    3                                                            
CONECT   44   40   47                                                       
CONECT   45   13   40                                                       
CONECT   46   39   49   51                                                  
CONECT   47   10   44   48   54                                             
CONECT   48   13   47                                                       
CONECT   49   46   50                                                       
CONECT   50   13   49                                                       
CONECT   51   46   53   55                                                  
CONECT   52    6                                                            
CONECT   53   14   51   56                                                  
CONECT   54   47   57                                                       
CONECT   55   51   59                                                       
CONECT   56   53   60                                                       
CONECT   57   54                                                            
CONECT   58    8                                                            
CONECT   59   55   60                                                       
CONECT   60   56   59                                                       
CONECT   61   16                                                            
CONECT   62   18                                                            
CONECT   63   40                                                            
MASTER        0    0    0    0    0    0    0    0   63    0  142    0
END
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3D PDB for HMDB0014681 (Vincristine)

COMPND    HMDB0014681
HETATM    1  C1  UNL     1      -8.366   2.864  -1.477  1.00  0.00           C  
HETATM    2  C2  UNL     1      -7.397   1.893  -2.083  1.00  0.00           C  
HETATM    3  C3  UNL     1      -6.128   1.826  -1.249  1.00  0.00           C  
HETATM    4  O1  UNL     1      -5.616   3.146  -1.263  1.00  0.00           O  
HETATM    5  C4  UNL     1      -5.152   0.960  -2.017  1.00  0.00           C  
HETATM    6  C5  UNL     1      -4.134   0.518  -0.979  1.00  0.00           C  
HETATM    7  C6  UNL     1      -4.929  -0.305   0.010  1.00  0.00           C  
HETATM    8  N1  UNL     1      -5.498   0.668   0.872  1.00  0.00           N  
HETATM    9  C7  UNL     1      -4.867   1.181   1.964  1.00  0.00           C  
HETATM   10  C8  UNL     1      -3.348   1.283   2.022  1.00  0.00           C  
HETATM   11  C9  UNL     1      -2.700  -0.006   1.768  1.00  0.00           C  
HETATM   12  C10 UNL     1      -2.097  -0.534   0.691  1.00  0.00           C  
HETATM   13  N2  UNL     1      -1.787  -1.832   0.959  1.00  0.00           N  
HETATM   14  C11 UNL     1      -2.164  -2.177   2.195  1.00  0.00           C  
HETATM   15  C12 UNL     1      -2.073  -3.353   2.934  1.00  0.00           C  
HETATM   16  C13 UNL     1      -2.556  -3.426   4.219  1.00  0.00           C  
HETATM   17  C14 UNL     1      -3.137  -2.311   4.776  1.00  0.00           C  
HETATM   18  C15 UNL     1      -3.212  -1.164   4.020  1.00  0.00           C  
HETATM   19  C16 UNL     1      -2.733  -1.062   2.720  1.00  0.00           C  
HETATM   20  C17 UNL     1      -1.796   0.047  -0.656  1.00  0.00           C  
HETATM   21  C18 UNL     1      -1.508   1.525  -0.569  1.00  0.00           C  
HETATM   22  O2  UNL     1      -0.844   1.933   0.389  1.00  0.00           O  
HETATM   23  O3  UNL     1      -1.962   2.386  -1.513  1.00  0.00           O  
HETATM   24  C19 UNL     1      -1.646   3.777  -1.360  1.00  0.00           C  
HETATM   25  C20 UNL     1      -0.442  -0.375  -1.172  1.00  0.00           C  
HETATM   26  C21 UNL     1       0.456  -1.051  -0.386  1.00  0.00           C  
HETATM   27  C22 UNL     1       1.743  -1.381  -0.832  1.00  0.00           C  
HETATM   28  C23 UNL     1       2.106  -1.009  -2.095  1.00  0.00           C  
HETATM   29  C24 UNL     1       1.209  -0.316  -2.907  1.00  0.00           C  
HETATM   30  C25 UNL     1      -0.061  -0.004  -2.435  1.00  0.00           C  
HETATM   31  O4  UNL     1      -0.939   0.683  -3.236  1.00  0.00           O  
HETATM   32  C26 UNL     1      -0.550   1.067  -4.537  1.00  0.00           C  
HETATM   33  N3  UNL     1       3.428  -1.459  -2.347  1.00  0.00           N  
HETATM   34  C27 UNL     1       4.041  -1.558  -3.601  1.00  0.00           C  
HETATM   35  O5  UNL     1       3.448  -1.242  -4.650  1.00  0.00           O  
HETATM   36  C28 UNL     1       4.009  -1.798  -1.073  1.00  0.00           C  
HETATM   37  C29 UNL     1       5.065  -0.863  -0.620  1.00  0.00           C  
HETATM   38  O6  UNL     1       6.176  -1.632  -0.245  1.00  0.00           O  
HETATM   39  C30 UNL     1       5.433   0.004  -1.804  1.00  0.00           C  
HETATM   40  O7  UNL     1       6.589  -0.077  -2.298  1.00  0.00           O  
HETATM   41  O8  UNL     1       4.499   0.875  -2.329  1.00  0.00           O  
HETATM   42  C31 UNL     1       4.771   1.722  -3.432  1.00  0.00           C  
HETATM   43  C32 UNL     1       4.530   0.005   0.478  1.00  0.00           C  
HETATM   44  O9  UNL     1       5.222   1.161   0.725  1.00  0.00           O  
HETATM   45  C33 UNL     1       4.821   2.464   0.525  1.00  0.00           C  
HETATM   46  C34 UNL     1       5.633   3.664   0.816  1.00  0.00           C  
HETATM   47  O10 UNL     1       3.684   2.621   0.064  1.00  0.00           O  
HETATM   48  C35 UNL     1       4.167  -0.863   1.649  1.00  0.00           C  
HETATM   49  C36 UNL     1       3.730   0.012   2.801  1.00  0.00           C  
HETATM   50  C37 UNL     1       4.745   0.953   3.330  1.00  0.00           C  
HETATM   51  C38 UNL     1       5.331  -1.661   2.129  1.00  0.00           C  
HETATM   52  C39 UNL     1       5.098  -2.789   2.768  1.00  0.00           C  
HETATM   53  C40 UNL     1       3.724  -3.254   3.005  1.00  0.00           C  
HETATM   54  N4  UNL     1       2.776  -2.883   2.030  1.00  0.00           N  
HETATM   55  C41 UNL     1       2.437  -3.975   1.193  1.00  0.00           C  
HETATM   56  C42 UNL     1       2.548  -3.562  -0.228  1.00  0.00           C  
HETATM   57  C43 UNL     1       2.889  -2.104  -0.157  1.00  0.00           C  
HETATM   58  C44 UNL     1       2.987  -1.720   1.262  1.00  0.00           C  
HETATM   59  C45 UNL     1      -2.949  -0.201  -1.577  1.00  0.00           C  
HETATM   60  C46 UNL     1      -6.422   1.461   0.137  1.00  0.00           C  
HETATM   61  H1  UNL     1      -9.130   3.124  -2.246  1.00  0.00           H  
HETATM   62  H2  UNL     1      -7.837   3.813  -1.235  1.00  0.00           H  
HETATM   63  H3  UNL     1      -8.832   2.494  -0.561  1.00  0.00           H  
HETATM   64  H4  UNL     1      -7.112   2.257  -3.092  1.00  0.00           H  
HETATM   65  H5  UNL     1      -7.856   0.896  -2.219  1.00  0.00           H  
HETATM   66  H6  UNL     1      -5.366   3.405  -2.186  1.00  0.00           H  
HETATM   67  H7  UNL     1      -4.659   1.575  -2.801  1.00  0.00           H  
HETATM   68  H8  UNL     1      -5.663   0.069  -2.419  1.00  0.00           H  
HETATM   69  H9  UNL     1      -3.768   1.455  -0.558  1.00  0.00           H  
HETATM   70  H10 UNL     1      -4.436  -1.163   0.431  1.00  0.00           H  
HETATM   71  H11 UNL     1      -5.828  -0.765  -0.525  1.00  0.00           H  
HETATM   72  H12 UNL     1      -5.213   2.244   2.152  1.00  0.00           H  
HETATM   73  H13 UNL     1      -5.178   0.638   2.883  1.00  0.00           H  
HETATM   74  H14 UNL     1      -3.176   1.556   3.109  1.00  0.00           H  
HETATM   75  H15 UNL     1      -2.977   2.177   1.544  1.00  0.00           H  
HETATM   76  H16 UNL     1      -1.353  -2.576   0.332  1.00  0.00           H  
HETATM   77  H17 UNL     1      -1.610  -4.204   2.458  1.00  0.00           H  
HETATM   78  H18 UNL     1      -2.465  -4.351   4.752  1.00  0.00           H  
HETATM   79  H19 UNL     1      -3.538  -2.315   5.797  1.00  0.00           H  
HETATM   80  H20 UNL     1      -3.673  -0.304   4.487  1.00  0.00           H  
HETATM   81  H21 UNL     1      -1.957   4.037  -0.307  1.00  0.00           H  
HETATM   82  H22 UNL     1      -2.179   4.422  -2.057  1.00  0.00           H  
HETATM   83  H23 UNL     1      -0.538   3.922  -1.359  1.00  0.00           H  
HETATM   84  H24 UNL     1       0.277  -1.311   0.640  1.00  0.00           H  
HETATM   85  H25 UNL     1       1.455  -0.003  -3.902  1.00  0.00           H  
HETATM   86  H26 UNL     1      -1.382   1.545  -5.092  1.00  0.00           H  
HETATM   87  H27 UNL     1       0.352   1.740  -4.506  1.00  0.00           H  
HETATM   88  H28 UNL     1      -0.242   0.150  -5.077  1.00  0.00           H  
HETATM   89  H29 UNL     1       5.056  -1.917  -3.672  1.00  0.00           H  
HETATM   90  H30 UNL     1       4.527  -2.797  -1.280  1.00  0.00           H  
HETATM   91  H31 UNL     1       6.329  -2.292  -0.960  1.00  0.00           H  
HETATM   92  H32 UNL     1       4.812   2.760  -3.040  1.00  0.00           H  
HETATM   93  H33 UNL     1       3.922   1.642  -4.130  1.00  0.00           H  
HETATM   94  H34 UNL     1       5.753   1.497  -3.900  1.00  0.00           H  
HETATM   95  H35 UNL     1       3.518   0.349   0.071  1.00  0.00           H  
HETATM   96  H36 UNL     1       6.639   3.304   1.123  1.00  0.00           H  
HETATM   97  H37 UNL     1       5.237   4.286   1.616  1.00  0.00           H  
HETATM   98  H38 UNL     1       5.784   4.210  -0.138  1.00  0.00           H  
HETATM   99  H39 UNL     1       3.316  -0.622   3.645  1.00  0.00           H  
HETATM  100  H40 UNL     1       2.826   0.630   2.515  1.00  0.00           H  
HETATM  101  H41 UNL     1       5.746   0.907   2.910  1.00  0.00           H  
HETATM  102  H42 UNL     1       4.400   2.023   3.294  1.00  0.00           H  
HETATM  103  H43 UNL     1       4.846   0.789   4.461  1.00  0.00           H  
HETATM  104  H44 UNL     1       6.365  -1.362   1.994  1.00  0.00           H  
HETATM  105  H45 UNL     1       5.980  -3.366   3.114  1.00  0.00           H  
HETATM  106  H46 UNL     1       3.785  -4.384   3.018  1.00  0.00           H  
HETATM  107  H47 UNL     1       3.385  -3.032   4.064  1.00  0.00           H  
HETATM  108  H48 UNL     1       1.419  -4.356   1.432  1.00  0.00           H  
HETATM  109  H49 UNL     1       3.114  -4.857   1.354  1.00  0.00           H  
HETATM  110  H50 UNL     1       3.315  -4.128  -0.800  1.00  0.00           H  
HETATM  111  H51 UNL     1       1.570  -3.740  -0.730  1.00  0.00           H  
HETATM  112  H52 UNL     1       2.089  -1.052   1.477  1.00  0.00           H  
HETATM  113  H53 UNL     1      -2.835   0.204  -2.563  1.00  0.00           H  
HETATM  114  H54 UNL     1      -3.266  -1.275  -1.556  1.00  0.00           H  
HETATM  115  H55 UNL     1      -6.620   2.386   0.747  1.00  0.00           H  
HETATM  116  H56 UNL     1      -7.413   0.915   0.171  1.00  0.00           H  
CONECT    1    2   61   62   63
CONECT    2    3   64   65
CONECT    3    4    5   60
CONECT    4   66
CONECT    5    6   67   68
CONECT    6    7   59   69
CONECT    7    8   70   71
CONECT    8    9   60
CONECT    9   10   72   73
CONECT   10   11   74   75
CONECT   11   12   12   19
CONECT   12   13   20
CONECT   13   14   76
CONECT   14   15   15   19
CONECT   15   16   77
CONECT   16   17   17   78
CONECT   17   18   79
CONECT   18   19   19   80
CONECT   20   21   25   59
CONECT   21   22   22   23
CONECT   23   24
CONECT   24   81   82   83
CONECT   25   26   26   30
CONECT   26   27   84
CONECT   27   28   28   57
CONECT   28   29   33
CONECT   29   30   30   85
CONECT   30   31
CONECT   31   32
CONECT   32   86   87   88
CONECT   33   34   36
CONECT   34   35   35   89
CONECT   36   37   57   90
CONECT   37   38   39   43
CONECT   38   91
CONECT   39   40   40   41
CONECT   41   42
CONECT   42   92   93   94
CONECT   43   44   48   95
CONECT   44   45
CONECT   45   46   47   47
CONECT   46   96   97   98
CONECT   48   49   51   58
CONECT   49   50   99  100
CONECT   50  101  102  103
CONECT   51   52   52  104
CONECT   52   53  105
CONECT   53   54  106  107
CONECT   54   55   58
CONECT   55   56  108  109
CONECT   56   57  110  111
CONECT   57   58
CONECT   58  112
CONECT   59  113  114
CONECT   60  115  116
END
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SMILES for HMDB0014681 (Vincristine)

[H][C@@]12N3CC[C@@]11C4=CC(=C(OC)C=C4N(C=O)[C@@]1([H])[C@](O)([C@H](OC(C)=O)[C@]2(CC)C=CC3)C(=O)OC)[C@]1(C[C@]2([H])CN(C[C@](O)(CC)C2)CCC2=C1NC1=CC=CC=C21)C(=O)OC
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INCHI for HMDB0014681 (Vincristine)

InChI=1S/C46H56N4O10/c1-7-42(55)22-28-23-45(40(53)58-5,36-30(14-18-48(24-28)25-42)29-12-9-10-13-33(29)47-36)32-20-31-34(21-35(32)57-4)50(26-51)38-44(31)16-19-49-17-11-15-43(8-2,37(44)49)39(60-27(3)52)46(38,56)41(54)59-6/h9-13,15,20-21,26,28,37-39,47,55-56H,7-8,14,16-19,22-25H2,1-6H3/t28-,37+,38-,39-,42+,43-,44-,45+,46+/m1/s1
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View in JSmolView Stereo Labels
Synonyms
ValueSource
(+)-VincristineChEBI
22-oxo-VincaleukoblastineChEBI
22-OxovincaleukoblastineChEBI
LeucristineChEBI
LeurocristineChEBI
OncovinChEBI
VincristinChEBI
VinkristinChEBI
TecnocrisKegg
Indole alkaloidHMDB
LCRHMDB
VCRHMDB
VINHMDB
VincristinaHMDB
Vincristine sulfateHMDB
VincrstineHMDB
VincrystineHMDB
Z-D-Val-lys(Z)-OHHMDB
CitomidHMDB
OncovineHMDB
Sulfate, vincristineHMDB
Vincasar PFSHMDB
VincrisulHMDB
OnkocristinHMDB
VincasarHMDB
FarmistinHMDB
PFS, VincasarHMDB
Vincristin bristolHMDB
Vincristin medacHMDB
VintecHMDB
CellcristinHMDB
Chemical FormulaC46H56N4O10
Average Molecular Weight824.9576
Monoisotopic Molecular Weight824.399644032
IUPAC Namemethyl (1R,9R,10S,11R,12R,19R)-11-(acetyloxy)-12-ethyl-4-[(13S,15S,17S)-17-ethyl-17-hydroxy-13-(methoxycarbonyl)-1,11-diazatetracyclo[13.3.1.0⁴,¹².0⁵,¹⁰]nonadeca-4(12),5,7,9-tetraen-13-yl]-8-formyl-10-hydroxy-5-methoxy-8,16-diazapentacyclo[10.6.1.0¹,⁹.0²,⁷.0¹⁶,¹⁹]nonadeca-2,4,6,13-tetraene-10-carboxylate
Traditional Namevincristine
CAS Registry Number57-22-7
SMILES
[H][C@@]12N3CC[C@@]11C4=CC(=C(OC)C=C4N(C=O)[C@@]1([H])[C@](O)([C@H](OC(C)=O)[C@]2(CC)C=CC3)C(=O)OC)[C@]1(C[C@]2([H])CN(C[C@](O)(CC)C2)CCC2=C1NC1=CC=CC=C21)C(=O)OC
InChI Identifier
InChI=1S/C46H56N4O10/c1-7-42(55)22-28-23-45(40(53)58-5,36-30(14-18-48(24-28)25-42)29-12-9-10-13-33(29)47-36)32-20-31-34(21-35(32)57-4)50(26-51)38-44(31)16-19-49-17-11-15-43(8-2,37(44)49)39(60-27(3)52)46(38,56)41(54)59-6/h9-13,15,20-21,26,28,37-39,47,55-56H,7-8,14,16-19,22-25H2,1-6H3/t28-,37+,38-,39-,42+,43-,44-,45+,46+/m1/s1
InChI KeyOGWKCGZFUXNPDA-XQKSVPLYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as dipeptides. These are organic compounds containing a sequence of exactly two alpha-amino acids joined by a peptide bond.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentDipeptides
Alternative Parents
Substituents
  • Alpha-dipeptide
  • Alpha-amino acid ester
  • Benzazepine
  • Alpha-amino acid or derivatives
  • Azepine
  • Fatty acid ester
  • Aralkylamine
  • Dicarboxylic acid or derivatives
  • Monocyclic benzene moiety
  • Fatty acyl
  • Benzenoid
  • Tertiary carboxylic acid amide
  • Carboxylic acid ester
  • Amino acid or derivatives
  • Amino acid
  • Lactam
  • Carboxamide group
  • Carboxylic acid
  • Secondary aliphatic amine
  • Azacycle
  • Secondary amine
  • Organoheterocyclic compound
  • Organic nitrogen compound
  • Organonitrogen compound
  • Carbonyl group
  • Organooxygen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Organopnictogen compound
  • Amine
  • Organic oxygen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
Disposition
Biological locationSource
Process
Naturally occurring process
Role
Biological role
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point220 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.03 g/LNot Available
LogP2.8Not Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.03 g/LALOGPS
logP3.36ALOGPS
logP3.13ChemAxon
logS-4.4ALOGPS
pKa (Strongest Acidic)10.85ChemAxon
pKa (Strongest Basic)8.66ChemAxon
Physiological Charge2ChemAxon
Hydrogen Acceptor Count9ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area171.17 ŲChemAxon
Rotatable Bond Count10ChemAxon
Refractivity221.48 m³·mol⁻¹ChemAxon
Polarizability88.59 ųChemAxon
Number of Rings9ChemAxon
BioavailabilityYesChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DeepCCS[M-2H]-289.48530932474
DeepCCS[M+Na]+262.98230932474
AllCCS[M+H]+271.032859911
AllCCS[M+H-H2O]+270.632859911
AllCCS[M+NH4]+271.432859911
AllCCS[M+Na]+271.532859911
AllCCS[M-H]-244.232859911
AllCCS[M+Na-2H]-249.432859911
AllCCS[M+HCOO]-255.232859911

Predicted Retention Times

Underivatized

Chromatographic MethodRetention TimeReference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.5.67 minutes32390414
Predicted by Siyang on May 30, 202213.6671 minutes33406817
Predicted by Siyang using ReTip algorithm on June 8, 20224.22 minutes32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid106.7 seconds40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid1870.7 seconds40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid152.3 seconds40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid247.8 seconds40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid174.1 seconds40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid123.7 seconds40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid507.7 seconds40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid488.6 seconds40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)680.5 seconds40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid1047.1 seconds40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid560.3 seconds40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid1697.1 seconds40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid337.6 seconds40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid411.9 seconds40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate284.1 seconds40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA257.1 seconds40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water10.9 seconds40023050

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Vincristine[H][C@@]12N3CC[C@@]11C4=CC(=C(OC)C=C4N(C=O)[C@@]1([H])[C@](O)([C@H](OC(C)=O)[C@]2(CC)C=CC3)C(=O)OC)[C@]1(C[C@]2([H])CN(C[C@](O)(CC)C2)CCC2=C1NC1=CC=CC=C21)C(=O)OC5546.5Standard polar33892256
Vincristine[H][C@@]12N3CC[C@@]11C4=CC(=C(OC)C=C4N(C=O)[C@@]1([H])[C@](O)([C@H](OC(C)=O)[C@]2(CC)C=CC3)C(=O)OC)[C@]1(C[C@]2([H])CN(C[C@](O)(CC)C2)CCC2=C1NC1=CC=CC=C21)C(=O)OC4848.1Standard non polar33892256
Vincristine[H][C@@]12N3CC[C@@]11C4=CC(=C(OC)C=C4N(C=O)[C@@]1([H])[C@](O)([C@H](OC(C)=O)[C@]2(CC)C=CC3)C(=O)OC)[C@]1(C[C@]2([H])CN(C[C@](O)(CC)C2)CCC2=C1NC1=CC=CC=C21)C(=O)OC5662.9Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Vincristine GC-MS (TMS_1_1) - 70eV, PositiveNot Available2021-10-19Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Vincristine GC-MS (TMS_1_2) - 70eV, PositiveNot Available2021-10-19Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Vincristine GC-MS (TMS_1_3) - 70eV, PositiveNot Available2021-10-19Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - Vincristine 35V, Positive-QTOFsplash10-004i-0000000090-ddde8bc651d70b277aa72021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Vincristine 35V, Negative-QTOFsplash10-00e9-0010001890-ec40da49423247b42f442021-09-20HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Vincristine 10V, Positive-QTOFsplash10-05r0-0000000960-3a843563d341d8bc8c672016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Vincristine 20V, Positive-QTOFsplash10-05ot-0000000910-19f858ef585f6c37c0672016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Vincristine 40V, Positive-QTOFsplash10-0537-1200000900-8774d71fd76cf13c57fe2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Vincristine 10V, Negative-QTOFsplash10-0c00-2005000950-4682841abaeccf6ff2502016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Vincristine 20V, Negative-QTOFsplash10-052r-1009000100-ce5fe6558a0993ae42c62016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Vincristine 40V, Negative-QTOFsplash10-0a4i-9002300800-16d21458a9981b9e680c2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Vincristine 10V, Positive-QTOFsplash10-004i-0000000390-aa3de8e6a5248eff1e032021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Vincristine 20V, Positive-QTOFsplash10-004j-0000000950-0e6c15ea67ad876951722021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Vincristine 40V, Positive-QTOFsplash10-0abc-9100112810-31f4dcec28eef9c1ce0c2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Vincristine 10V, Negative-QTOFsplash10-0a4i-9000000420-c00fa346c22549393c802021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Vincristine 20V, Negative-QTOFsplash10-0a4i-8000000900-54ffe3b7f7c10887482f2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Vincristine 40V, Negative-QTOFsplash10-0002-4040000900-727e48a803b558914e662021-09-24Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Membrane
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00541 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00541 details
Abnormal Concentrations
Not Available
Predicted Concentrations
BiospecimenValueOriginal ageOriginal sexOriginal conditionComments
Blood0.000 uMAdult (>18 years old)BothNormalPredicted based on drug qualities
Blood0.000 umol/mmol creatinineAdult (>18 years old)BothNormalPredicted based on drug qualities
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB00541
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDC00001783
Chemspider ID5758
KEGG Compound IDC07204
BioCyc IDCPD-19894
BiGG IDNot Available
Wikipedia LinkVincristine
METLIN IDNot Available
PubChem Compound5978
PDB IDNot Available
ChEBI ID28445
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Graf WD, Chance PF, Lensch MW, Eng LJ, Lipe HP, Bird TD: Severe vincristine neuropathy in Charcot-Marie-Tooth disease type 1A. Cancer. 1996 Apr 1;77(7):1356-62. [PubMed:8608515 ]
  2. Gidding CE, Kellie SJ, Kamps WA, de Graaf SS: Vincristine revisited. Crit Rev Oncol Hematol. 1999 Feb;29(3):267-87. [PubMed:10226730 ]
  3. JOHNSON IS, ARMSTRONG JG, GORMAN M, BURNETT JP Jr: THE VINCA ALKALOIDS: A NEW CLASS OF ONCOLYTIC AGENTS. Cancer Res. 1963 Sep;23:1390-427. [PubMed:14070392 ]
  4. Qweider M, Gilsbach JM, Rohde V: Inadvertent intrathecal vincristine administration: a neurosurgical emergency. Case report. J Neurosurg Spine. 2007 Mar;6(3):280-3. [PubMed:17355029 ]
  5. (). FDA label . .

Only showing the first 10 proteins. There are 12 proteins in total.

Show all enzymes and transporters

Enzymes

Enzyme Details
1. Cytochrome P450 3A4
General function:
Involved in monooxygenase activity
Specific function:
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation reactions (e.g. caffeine 8-oxidation, omeprazole sulphoxidation, midazolam 1'-hydroxylation and midazolam 4-hydroxylation) of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. Acts as a 1,8-cineole 2-exo-monooxygenase. The enzyme also hydroxylates etoposide.
Gene Name:
CYP3A4
Uniprot ID:
P08684
Molecular weight:
57255.585
References
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]
Enzyme Details
2. Cytochrome P450 3A5
General function:
Involved in monooxygenase activity
Specific function:
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics.
Gene Name:
CYP3A5
Uniprot ID:
P20815
Molecular weight:
57108.065
References
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]
Enzyme Details
3. Cytochrome P450 3A7
General function:
Involved in monooxygenase activity
Specific function:
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics.
Gene Name:
CYP3A7
Uniprot ID:
P24462
Molecular weight:
57525.03
Enzyme Details
4. Tubulin beta chain
General function:
Involved in structural molecule activity
Specific function:
Tubulin is the major constituent of microtubules. It binds two moles of GTP, one at an exchangeable site on the beta chain and one at a non-exchangeable site on the alpha-chain
Gene Name:
TUBB
Uniprot ID:
P07437
Molecular weight:
49670.5
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284 ]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423 ]
  3. Kurtzberg LS, Roth SD, Bagley RG, Rouleau C, Yao M, Crawford JL, Krumbholz RD, Schmid SM, Teicher BA: Bone marrow CFU-GM and human tumor xenograft efficacy of three tubulin binding agents. Cancer Chemother Pharmacol. 2009 Oct;64(5):1029-38. doi: 10.1007/s00280-009-0959-z. Epub 2009 Mar 10. [PubMed:19277662 ]
  4. Gan PP, McCarroll JA, Po'uha ST, Kamath K, Jordan MA, Kavallaris M: Microtubule dynamics, mitotic arrest, and apoptosis: drug-induced differential effects of betaIII-tubulin. Mol Cancer Ther. 2010 May;9(5):1339-48. doi: 10.1158/1535-7163.MCT-09-0679. Epub 2010 May 4. [PubMed:20442307 ]
Enzyme Details
5. Tubulin alpha-4A chain
General function:
Involved in structural molecule activity
Specific function:
Tubulin is the major constituent of microtubules. It binds two moles of GTP, one at an exchangeable site on the beta chain and one at a non-exchangeable site on the alpha-chain
Gene Name:
TUBA4A
Uniprot ID:
P68366
Molecular weight:
49924.0
References
  1. Yasui M, Koyama N, Koizumi T, Senda-Murata K, Takashima Y, Hayashi M, Sugimoto K, Honma M: Live cell imaging of micronucleus formation and development. Mutat Res. 2010 Oct 13;692(1-2):12-8. doi: 10.1016/j.mrfmmm.2010.07.009. Epub 2010 Aug 5. [PubMed:20691709 ]
  2. Gan PP, McCarroll JA, Po'uha ST, Kamath K, Jordan MA, Kavallaris M: Microtubule dynamics, mitotic arrest, and apoptosis: drug-induced differential effects of betaIII-tubulin. Mol Cancer Ther. 2010 May;9(5):1339-48. doi: 10.1158/1535-7163.MCT-09-0679. Epub 2010 May 4. [PubMed:20442307 ]
  3. Vilpo JA, Koski T, Vilpo LM: Selective toxicity of vincristine against chronic lymphocytic leukemia cells in vitro. Eur J Haematol. 2000 Dec;65(6):370-8. [PubMed:11168494 ]

Transporters

Enzyme Details
1. Canalicular multispecific organic anion transporter 1
General function:
Involved in ATP binding
Specific function:
Mediates hepatobiliary excretion of numerous organic anions. May function as a cellular cisplatin transporter
Gene Name:
ABCC2
Uniprot ID:
Q92887
Molecular weight:
174205.6
References
  1. Tang F, Horie K, Borchardt RT: Are MDCK cells transfected with the human MRP2 gene a good model of the human intestinal mucosa? Pharm Res. 2002 Jun;19(6):773-9. [PubMed:12134946 ]
  2. Hong J, Lambert JD, Lee SH, Sinko PJ, Yang CS: Involvement of multidrug resistance-associated proteins in regulating cellular levels of (-)-epigallocatechin-3-gallate and its methyl metabolites. Biochem Biophys Res Commun. 2003 Oct 10;310(1):222-7. [PubMed:14511674 ]
  3. Ishikawa T, Muller M, Klunemann C, Schaub T, Keppler D: ATP-dependent primary active transport of cysteinyl leukotrienes across liver canalicular membrane. Role of the ATP-dependent transport system for glutathione S-conjugates. J Biol Chem. 1990 Nov 5;265(31):19279-86. [PubMed:2172249 ]
  4. Chen ZS, Kawabe T, Ono M, Aoki S, Sumizawa T, Furukawa T, Uchiumi T, Wada M, Kuwano M, Akiyama SI: Effect of multidrug resistance-reversing agents on transporting activity of human canalicular multispecific organic anion transporter. Mol Pharmacol. 1999 Dec;56(6):1219-28. [PubMed:10570049 ]
Enzyme Details
2. Multidrug resistance-associated protein 1
General function:
Involved in ATP binding
Specific function:
Mediates export of organic anions and drugs from the cytoplasm. Mediates ATP-dependent transport of glutathione and glutathione conjugates, leukotriene C4, estradiol-17-beta-o- glucuronide, methotrexate, antiviral drugs and other xenobiotics. Confers resistance to anticancer drugs. Hydrolyzes ATP with low efficiency
Gene Name:
ABCC1
Uniprot ID:
P33527
Molecular weight:
171589.5
References
  1. Loe DW, Almquist KC, Cole SP, Deeley RG: ATP-dependent 17 beta-estradiol 17-(beta-D-glucuronide) transport by multidrug resistance protein (MRP). Inhibition by cholestatic steroids. J Biol Chem. 1996 Apr 19;271(16):9683-9. [PubMed:8621644 ]
  2. Godinot N, Iversen PW, Tabas L, Xia X, Williams DC, Dantzig AH, Perry WL 3rd: Cloning and functional characterization of the multidrug resistance-associated protein (MRP1/ABCC1) from the cynomolgus monkey. Mol Cancer Ther. 2003 Mar;2(3):307-16. [PubMed:12657726 ]
  3. Nunoya K, Grant CE, Zhang D, Cole SP, Deeley RG: Molecular cloning and pharmacological characterization of rat multidrug resistance protein 1 (mrp1). Drug Metab Dispos. 2003 Aug;31(8):1016-26. [PubMed:12867490 ]
  4. Sumizawa T, Chen ZS, Chuman Y, Seto K, Furukawa T, Haraguchi M, Tani A, Shudo N, Akiyama SI: Reversal of multidrug resistance-associated protein-mediated drug resistance by the pyridine analog PAK-104P. Mol Pharmacol. 1997 Mar;51(3):399-405. [PubMed:9058594 ]
  5. Renes J, de Vries EG, Nienhuis EF, Jansen PL, Muller M: ATP- and glutathione-dependent transport of chemotherapeutic drugs by the multidrug resistance protein MRP1. Br J Pharmacol. 1999 Feb;126(3):681-8. [PubMed:10188979 ]
  6. Stride BD, Grant CE, Loe DW, Hipfner DR, Cole SP, Deeley RG: Pharmacological characterization of the murine and human orthologs of multidrug-resistance protein in transfected human embryonic kidney cells. Mol Pharmacol. 1997 Sep;52(3):344-53. [PubMed:9281595 ]
Enzyme Details
3. Canalicular multispecific organic anion transporter 2
General function:
Involved in ATP binding
Specific function:
May act as an inducible transporter in the biliary and intestinal excretion of organic anions. Acts as an alternative route for the export of bile acids and glucuronides from cholestatic hepatocytes
Gene Name:
ABCC3
Uniprot ID:
O15438
Molecular weight:
169341.1
References
  1. Zeng H, Chen ZS, Belinsky MG, Rea PA, Kruh GD: Transport of methotrexate (MTX) and folates by multidrug resistance protein (MRP) 3 and MRP1: effect of polyglutamylation on MTX transport. Cancer Res. 2001 Oct 1;61(19):7225-32. [PubMed:11585759 ]
Enzyme Details
4. Bile salt export pump
General function:
Involved in ATP binding
Specific function:
Involved in the ATP-dependent secretion of bile salts into the canaliculus of hepatocytes
Gene Name:
ABCB11
Uniprot ID:
O95342
Molecular weight:
146405.8
References
  1. Lecureur V, Sun D, Hargrove P, Schuetz EG, Kim RB, Lan LB, Schuetz JD: Cloning and expression of murine sister of P-glycoprotein reveals a more discriminating transporter than MDR1/P-glycoprotein. Mol Pharmacol. 2000 Jan;57(1):24-35. [PubMed:10617675 ]
Enzyme Details
5. Multidrug resistance protein 1
General function:
Involved in ATP binding
Specific function:
Energy-dependent efflux pump responsible for decreased drug accumulation in multidrug-resistant cells
Gene Name:
ABCB1
Uniprot ID:
P08183
Molecular weight:
141477.3
References
  1. Arora A, Shukla Y: Modulation of vinca-alkaloid induced P-glycoprotein expression by indole-3-carbinol. Cancer Lett. 2003 Jan 28;189(2):167-73. [PubMed:12490309 ]
  2. Polli JW, Wring SA, Humphreys JE, Huang L, Morgan JB, Webster LO, Serabjit-Singh CS: Rational use of in vitro P-glycoprotein assays in drug discovery. J Pharmacol Exp Ther. 2001 Nov;299(2):620-8. [PubMed:11602674 ]
  3. Tang F, Horie K, Borchardt RT: Are MDCK cells transfected with the human MDR1 gene a good model of the human intestinal mucosa? Pharm Res. 2002 Jun;19(6):765-72. [PubMed:12134945 ]
  4. Doppenschmitt S, Langguth P, Regardh CG, Andersson TB, Hilgendorf C, Spahn-Langguth H: Characterization of binding properties to human P-glycoprotein: development of a [3H]verapamil radioligand-binding assay. J Pharmacol Exp Ther. 1999 Jan;288(1):348-57. [PubMed:9862789 ]
  5. Nagy H, Goda K, Fenyvesi F, Bacso Z, Szilasi M, Kappelmayer J, Lustyik G, Cianfriglia M, Szabo G Jr: Distinct groups of multidrug resistance modulating agents are distinguished by competition of P-glycoprotein-specific antibodies. Biochem Biophys Res Commun. 2004 Mar 19;315(4):942-9. [PubMed:14985103 ]
  6. Li D, Jang SH, Kim J, Wientjes MG, Au JL: Enhanced drug-induced apoptosis associated with P-glycoprotein overexpression is specific to antimicrotubule agents. Pharm Res. 2003 Jan;20(1):45-50. [PubMed:12608535 ]
  7. Lecureur V, Sun D, Hargrove P, Schuetz EG, Kim RB, Lan LB, Schuetz JD: Cloning and expression of murine sister of P-glycoprotein reveals a more discriminating transporter than MDR1/P-glycoprotein. Mol Pharmacol. 2000 Jan;57(1):24-35. [PubMed:10617675 ]
  8. Kuo CC, Hsieh HP, Pan WY, Chen CP, Liou JP, Lee SJ, Chang YL, Chen LT, Chen CT, Chang JY: BPR0L075, a novel synthetic indole compound with antimitotic activity in human cancer cells, exerts effective antitumoral activity in vivo. Cancer Res. 2004 Jul 1;64(13):4621-8. [PubMed:15231674 ]
  9. Woodahl EL, Crouthamel MH, Bui T, Shen DD, Ho RJ: MDR1 (ABCB1) G1199A (Ser400Asn) polymorphism alters transepithelial permeability and sensitivity to anticancer agents. Cancer Chemother Pharmacol. 2009 Jun;64(1):183-8. doi: 10.1007/s00280-008-0906-4. Epub 2009 Jan 4. [PubMed:19123050 ]
  10. Tiwari AK, Sodani K, Wang SR, Kuang YH, Ashby CR Jr, Chen X, Chen ZS: Nilotinib (AMN107, Tasigna) reverses multidrug resistance by inhibiting the activity of the ABCB1/Pgp and ABCG2/BCRP/MXR transporters. Biochem Pharmacol. 2009 Jul 15;78(2):153-61. doi: 10.1016/j.bcp.2009.04.002. Epub 2009 Apr 11. [PubMed:19427995 ]
  11. Noguchi K, Kawahara H, Kaji A, Katayama K, Mitsuhashi J, Sugimoto Y: Substrate-dependent bidirectional modulation of P-glycoprotein-mediated drug resistance by erlotinib. Cancer Sci. 2009 Sep;100(9):1701-7. doi: 10.1111/j.1349-7006.2009.01213.x. Epub 2009 May 12. [PubMed:19493273 ]
Enzyme Details
6. ATP-binding cassette sub-family G member 2
General function:
Involved in ATP binding
Specific function:
Xenobiotic transporter that may play an important role in the exclusion of xenobiotics from the brain. May be involved in brain-to-blood efflux. Appears to play a major role in the multidrug resistance phenotype of several cancer cell lines. When overexpressed, the transfected cells become resistant to mitoxantrone, daunorubicin and doxorubicin, display diminished intracellular accumulation of daunorubicin, and manifest an ATP- dependent increase in the efflux of rhodamine 123
Gene Name:
ABCG2
Uniprot ID:
Q9UNQ0
Molecular weight:
72313.5
References
  1. Allen JD, Van Dort SC, Buitelaar M, van Tellingen O, Schinkel AH: Mouse breast cancer resistance protein (Bcrp1/Abcg2) mediates etoposide resistance and transport, but etoposide oral availability is limited primarily by P-glycoprotein. Cancer Res. 2003 Mar 15;63(6):1339-44. [PubMed:12649196 ]
Enzyme Details
7. Solute carrier family 22 member 3
General function:
Involved in transmembrane transport
Specific function:
Mediates potential-dependent transport of a variety of organic cations. May play a significant role in the disposition of cationic neurotoxins and neurotransmitters in the brain
Gene Name:
SLC22A3
Uniprot ID:
O75751
Molecular weight:
61279.5
References
  1. Shnitsar V, Eckardt R, Gupta S, Grottker J, Muller GA, Koepsell H, Burckhardt G, Hagos Y: Expression of human organic cation transporter 3 in kidney carcinoma cell lines increases chemosensitivity to melphalan, irinotecan, and vincristine. Cancer Res. 2009 Feb 15;69(4):1494-501. doi: 10.1158/0008-5472.CAN-08-2483. Epub 2009 Feb 3. [PubMed:19190342 ]

Only showing the first 10 proteins. There are 12 proteins in total.

Show all enzymes and transporters