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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2013-06-18 17:48:10 UTC

Update Date

2019-07-23 07:14:48 UTC

HMDB ID

HMDB0060661

Secondary Accession Numbers

HMDB60661

Metabolite Identification

Common Name

APC

Description

APC is a metabolite of irinotecan. Irinotecan is a drug used for the treatment of cancer. Irinotecan prevents DNA from unwinding by inhibition of topoisomerase 1. In chemical terms, it is a semisynthetic analogue of the natural alkaloid camptothecin. Its main use is in colon cancer, in particular, in combination with other chemotherapy agents. This includes the regimen FOLFIRI, which consists of infusional 5-fluorouracil, leucovorin, and irinotecan. Irinotecan received accelerated approval by the U.S. (Wikipedia )

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

 
  Mrv0541 06181310482D          
 
 45 50  0  0  1  0            999 V2000
   15.0064  -11.3509    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0064  -12.1759    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   16.4089  -12.1759    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.4089  -11.3509    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.7076  -10.9384    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.1514  -12.5885    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   17.8527  -12.1759    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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 42 43  1  0  0  0  0
 43 44  1  0  0  0  0
 43 45  2  0  0  0  0
M  END

HMDB0060661
     RDKit          3D
APC
 83 88  0  0  0  0  0  0  0  0999 V2000
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 45 82  1  0
 45 83  1  0
M  END

 
  Mrv0541 06181310482D          
 
 45 50  0  0  1  0            999 V2000
   15.0064  -11.3509    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0064  -12.1759    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.7076  -12.5885    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   17.1514  -10.9384    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2638  -10.9384    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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   12.1188  -11.3509    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7162   -9.7008    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   18.6365  -12.4234    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.1315  -11.7634    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   18.6365  -11.1034    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.9153  -11.7634    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.3278  -12.4647    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.9566  -13.1660    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.0903  -13.1660    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.3691  -13.8673    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   21.1941  -13.8673    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.5654  -13.1660    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.1528  -12.4647    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.3278  -11.0209    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.6066  -14.6098    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.1514  -10.1133    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.4089   -9.7008    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.5440  -13.8673    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.3691  -14.7335    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.1315  -14.6098    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9950  -10.1323    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2787   -9.7187    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5624  -10.1323    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8461   -9.7187    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1297  -10.1323    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4134   -9.7187    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1297  -10.9593    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  1  6  1  0  0  0  0
  4  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
  5 10  1  0  0  0  0
  1 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 12 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 14 19  1  0  0  0  0
 17 20  1  0  0  0  0
  8 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
  9 23  1  0  0  0  0
 22 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  2  0  0  0  0
 26 27  1  0  0  0  0
 26 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
 25 31  1  0  0  0  0
 27 21  2  0  0  0  0
 24 32  2  0  0  0  0
 29 33  2  0  0  0  0
 10 34  1  0  0  0  0
 34 35  1  0  0  0  0
 28 36  1  6  0  0  0
 28 37  1  1  0  0  0
 36 38  1  0  0  0  0
 20 39  1  0  0  0  0
 39 40  1  0  0  0  0
 40 41  1  0  0  0  0
 41 42  1  0  0  0  0
 42 43  1  0  0  0  0
 43 44  1  0  0  0  0
 43 45  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0060661

> <DATABASE_NAME>
hmdb

> <SMILES>
CCC1=C2CN3C(=CC4=C(COC(=O)[C@]4(O)CC)C3=O)C2=NC2=CC=C(OC(=O)N3CCC(CC3)NCCCCC(O)=O)C=C12

> <INCHI_IDENTIFIER>
InChI=1S/C33H38N4O8/c1-3-21-22-15-20(45-32(42)36-13-10-19(11-14-36)34-12-6-5-7-28(38)39)8-9-26(22)35-29-23(21)17-37-27(29)16-25-24(30(37)40)18-44-31(41)33(25,43)4-2/h8-9,15-16,19,34,43H,3-7,10-14,17-18H2,1-2H3,(H,38,39)/t33-/m0/s1

> <INCHI_KEY>
BSVVZICJFYZDJJ-XIFFEERXSA-N

> <FORMULA>
C33H38N4O8

> <MOLECULAR_WEIGHT>
618.6768

> <EXACT_MASS>
618.268964212

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_AVERAGE_POLARIZABILITY>
66.49793612978038

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
5-{[1-({[(19S)-10,19-diethyl-19-hydroxy-14,18-dioxo-17-oxa-3,13-diazapentacyclo[11.8.0.0²,¹¹.0⁴,⁹.0¹⁵,²⁰]henicosa-1(21),2,4,6,8,10,15(20)-heptaen-7-yl]oxy}carbonyl)piperidin-4-yl]amino}pentanoic acid

> <ALOGPS_LOGP>
2.32

> <JCHEM_LOGP>
-0.48129612258468624

> <ALOGPS_LOGS>
-4.11

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
11.742380674262725

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.658114003876758

> <JCHEM_PKA_STRONGEST_BASIC>
10.580728133077663

> <JCHEM_POLAR_SURFACE_AREA>
158.6

> <JCHEM_REFRACTIVITY>
164.03360000000004

> <JCHEM_ROTATABLE_BOND_COUNT>
10

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
4.84e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
5-{[1-({[(19S)-10,19-diethyl-19-hydroxy-14,18-dioxo-17-oxa-3,13-diazapentacyclo[11.8.0.0²,¹¹.0⁴,⁹.0¹⁵,²⁰]henicosa-1(21),2,4,6,8,10,15(20)-heptaen-7-yl]oxy}carbonyl)piperidin-4-yl]amino}pentanoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0060661
     RDKit          3D
APC
 83 88  0  0  0  0  0  0  0  0999 V2000
   -2.2780   -3.1333   -1.9370 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2202   -2.7682   -0.4728 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8116   -1.4442   -0.2016 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1858   -1.2555   -0.1461 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7793   -0.0450    0.0803 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9491    0.9999    0.2538 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6137    0.8832    0.2121 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8131    2.0035    0.3898 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4383    1.8739    0.3341 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2021    0.6992    0.1119 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5370    0.4974    0.0405 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5892    1.2518    0.4527 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3185    2.3455    0.9917 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9212    0.7573    0.2451 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.0225    1.5873    0.6403 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3410    1.2271   -0.0199 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5131   -0.2380   -0.1322 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6728   -0.7932   -0.5833 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.8617   -0.7860    0.1373 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6299    0.4539    0.3932 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9301    0.1508    1.1560 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8750   -0.7378    0.4172 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3197   -0.1189   -0.8255 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9182   -0.7013   -1.7507 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.0741    1.2540   -1.0430 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3780   -0.6992   -1.0999 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1040   -0.5706   -0.3310 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6244   -0.4183   -0.0641 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9988   -0.3531   -0.0190 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2227   -0.2365    0.0590 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3032    0.6473    0.2208 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.6054    0.2439    0.1527 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.8169   -1.1314   -0.0935 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7322   -1.9512   -0.2446 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9299   -3.1912   -0.4673 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4639   -1.5349   -0.1731 N   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2229   -2.2889   -0.3097 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.2116   -1.6183   -0.1938 C   0  0  0  0  0  0  0  0  0  0  0  0
  -11.0795   -0.6886   -0.8259 O   0  0  0  0  0  0  0  0  0  0  0  0
  -10.7880    0.6504   -0.7660 C   0  0  0  0  0  0  0  0  0  0  0  0
  -11.2704    1.4902   -1.5199 O   0  0  0  0  0  0  0  0  0  0  0  0
   -9.8217    1.0659    0.2980 C   0  0  1  0  0  0  0  0  0  0  0  0
  -10.4332    0.6111    1.5008 O   0  0  0  0  0  0  0  0  0  0  0  0
   -9.6618    2.5322    0.3117 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.8399    3.0204    1.4533 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3299   -3.5895   -2.2611 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.2493   -2.9437   -0.0491 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9118   -3.5009    0.0453 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2446    2.9999    0.5754 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1288    2.7760    0.4744 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8197    2.6510    0.3085 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0807    1.6132    1.7387 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1175    1.7000    0.5693 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3518    1.7220   -1.0254 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1440   -0.6759    0.8573 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7884   -0.9767   -1.6008 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.6139   -1.5394   -0.3154 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.7206   -1.2782    1.1749 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.0582    1.0742    1.1368 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.8880    1.0226   -0.4952 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.6218   -0.3506    2.1101 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.4154    1.0869    1.4588 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.4815   -1.7505    0.2126 H   0  0  0  0  0  0  0  0  0  0  0  0
   12.7514   -0.9215    1.1070 H   0  0  0  0  0  0  0  0  0  0  0  0
   12.1172    1.9168   -0.2893 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5066   -1.7560   -1.3720 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3552   -0.0320   -1.9724 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2538   -0.7023   -1.0602 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0252   -1.3075    0.4991 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1481   -1.3612   -0.2461 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0807    1.6854    0.3936 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1152   -2.7285   -1.3134 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0817   -3.0370    0.5002 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.6428   -1.9693    0.7532 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.1696   -2.5166   -0.8865 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.8200    0.0133    1.9949 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.2590    2.9154   -0.6814 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.6780    3.0194    0.3622 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5143    2.2341    2.1423 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0263    3.6953    1.1298 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.4823    3.6961    2.1224 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
 12 14  1  0
 14 15  1  0
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 21 22  1  0
 22 23  1  0
 23 24  2  0
 23 25  1  0
 17 26  1  0
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  5 30  1  0
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 34 35  2  0
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 36 37  1  0
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 39 40  1  0
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 40 42  1  0
 42 43  1  1
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 44 45  1  0
 29  3  1  0
 36 30  1  0
 37  4  1  0
 29  7  1  0
 42 32  1  0
 27 14  1  0
  1 46  1  0
  1 47  1  0
  1 48  1  0
  2 49  1  0
  2 50  1  0
  8 51  1  0
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 15 53  1  0
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 31 73  1  0
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 38 76  1  0
 38 77  1  0
 43 78  1  0
 44 79  1  0
 44 80  1  0
 45 81  1  0
 45 82  1  0
 45 83  1  0
M  END

HEADER    PROTEIN                                 18-JUN-13   NONE
TITLE     NULL                                                        
COMPND    MOLECULE:                                                   
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   18-JUN-13         0                                  
HETATM    1  C   UNK     0      28.012 -21.188   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      28.012 -22.728   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      29.321 -23.498   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      30.630 -22.728   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      30.630 -21.188   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      29.321 -20.418   0.000  0.00  0.00           C+0
HETATM    7  N   UNK     0      32.016 -23.498   0.000  0.00  0.00           N+0
HETATM    8  C   UNK     0      33.325 -22.728   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      33.325 -21.188   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      32.016 -20.418   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      26.626 -20.418   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0      25.317 -21.188   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0      25.317 -22.728   0.000  0.00  0.00           O+0
HETATM   14  N   UNK     0      24.008 -20.418   0.000  0.00  0.00           N+0
HETATM   15  C   UNK     0      24.008 -18.878   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      22.622 -18.108   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      21.313 -18.878   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      21.313 -20.418   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      22.622 -21.188   0.000  0.00  0.00           C+0
HETATM   20  N   UNK     0      20.004 -18.108   0.000  0.00  0.00           N+0
HETATM   21  C   UNK     0      34.788 -23.190   0.000  0.00  0.00           C+0
HETATM   22  N   UNK     0      35.712 -21.958   0.000  0.00  0.00           N+0
HETATM   23  C   UNK     0      34.788 -20.726   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      37.175 -21.958   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      37.945 -23.267   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      37.252 -24.576   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      35.635 -24.576   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      38.022 -25.886   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      39.562 -25.886   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0      40.255 -24.576   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0      39.485 -23.267   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0      37.945 -20.572   0.000  0.00  0.00           O+0
HETATM   33  O   UNK     0      40.332 -27.272   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0      32.016 -18.878   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      30.630 -18.108   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      36.482 -25.886   0.000  0.00  0.00           C+0
HETATM   37  O   UNK     0      38.022 -27.503   0.000  0.00  0.00           O+0
HETATM   38  C   UNK     0      35.712 -27.272   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0      18.657 -18.914   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0      17.320 -18.142   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0      15.983 -18.914   0.000  0.00  0.00           C+0
HETATM   42  C   UNK     0      14.646 -18.142   0.000  0.00  0.00           C+0
HETATM   43  C   UNK     0      13.309 -18.914   0.000  0.00  0.00           C+0
HETATM   44  O   UNK     0      11.972 -18.142   0.000  0.00  0.00           O+0
HETATM   45  O   UNK     0      13.309 -20.457   0.000  0.00  0.00           O+0
CONECT    1    2    6   11                                                  
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5    7                                                  
CONECT    5    4    6   10                                                  
CONECT    6    5    1                                                       
CONECT    7    4    8                                                       
CONECT    8    7    9   21                                                  
CONECT    9    8   10   23                                                  
CONECT   10    9    5   34                                                  
CONECT   11    1   12                                                       
CONECT   12   11   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12   15   19                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18   20                                                  
CONECT   18   17   19                                                       
CONECT   19   18   14                                                       
CONECT   20   17   39                                                       
CONECT   21    8   22   27                                                  
CONECT   22   21   23   24                                                  
CONECT   23   22    9                                                       
CONECT   24   22   25   32                                                  
CONECT   25   24   26   31                                                  
CONECT   26   25   27   28                                                  
CONECT   27   26   21                                                       
CONECT   28   26   29   36   37                                             
CONECT   29   28   30   33                                                  
CONECT   30   29   31                                                       
CONECT   31   30   25                                                       
CONECT   32   24                                                            
CONECT   33   29                                                            
CONECT   34   10   35                                                       
CONECT   35   34                                                            
CONECT   36   28   38                                                       
CONECT   37   28                                                            
CONECT   38   36                                                            
CONECT   39   20   40                                                       
CONECT   40   39   41                                                       
CONECT   41   40   42                                                       
CONECT   42   41   43                                                       
CONECT   43   42   44   45                                                  
CONECT   44   43                                                            
CONECT   45   43                                                            
MASTER        0    0    0    0    0    0    0    0   45    0  100    0
END

COMPND    HMDB0060661
HETATM    1  C1  UNL     1      -2.278  -3.133  -1.937  1.00  0.00           C  
HETATM    2  C2  UNL     1      -2.220  -2.768  -0.473  1.00  0.00           C  
HETATM    3  C3  UNL     1      -2.812  -1.444  -0.202  1.00  0.00           C  
HETATM    4  C4  UNL     1      -4.186  -1.255  -0.146  1.00  0.00           C  
HETATM    5  C5  UNL     1      -4.779  -0.045   0.080  1.00  0.00           C  
HETATM    6  N1  UNL     1      -3.949   1.000   0.254  1.00  0.00           N  
HETATM    7  C6  UNL     1      -2.614   0.883   0.212  1.00  0.00           C  
HETATM    8  C7  UNL     1      -1.813   2.003   0.390  1.00  0.00           C  
HETATM    9  C8  UNL     1      -0.438   1.874   0.334  1.00  0.00           C  
HETATM   10  C9  UNL     1       0.202   0.699   0.112  1.00  0.00           C  
HETATM   11  O1  UNL     1       1.537   0.497   0.041  1.00  0.00           O  
HETATM   12  C10 UNL     1       2.589   1.252   0.453  1.00  0.00           C  
HETATM   13  O2  UNL     1       2.318   2.345   0.992  1.00  0.00           O  
HETATM   14  N2  UNL     1       3.921   0.757   0.245  1.00  0.00           N  
HETATM   15  C11 UNL     1       5.022   1.587   0.640  1.00  0.00           C  
HETATM   16  C12 UNL     1       6.341   1.227  -0.020  1.00  0.00           C  
HETATM   17  C13 UNL     1       6.513  -0.238  -0.132  1.00  0.00           C  
HETATM   18  N3  UNL     1       7.673  -0.793  -0.583  1.00  0.00           N  
HETATM   19  C14 UNL     1       8.862  -0.786   0.137  1.00  0.00           C  
HETATM   20  C15 UNL     1       9.630   0.454   0.393  1.00  0.00           C  
HETATM   21  C16 UNL     1      10.930   0.151   1.156  1.00  0.00           C  
HETATM   22  C17 UNL     1      11.875  -0.738   0.417  1.00  0.00           C  
HETATM   23  C18 UNL     1      12.320  -0.119  -0.826  1.00  0.00           C  
HETATM   24  O3  UNL     1      12.918  -0.701  -1.751  1.00  0.00           O  
HETATM   25  O4  UNL     1      12.074   1.254  -1.043  1.00  0.00           O  
HETATM   26  C19 UNL     1       5.378  -0.699  -1.100  1.00  0.00           C  
HETATM   27  C20 UNL     1       4.104  -0.571  -0.331  1.00  0.00           C  
HETATM   28  C21 UNL     1      -0.624  -0.418  -0.064  1.00  0.00           C  
HETATM   29  C22 UNL     1      -1.999  -0.353  -0.019  1.00  0.00           C  
HETATM   30  C23 UNL     1      -6.223  -0.237   0.059  1.00  0.00           C  
HETATM   31  C24 UNL     1      -7.303   0.647   0.221  1.00  0.00           C  
HETATM   32  C25 UNL     1      -8.605   0.244   0.153  1.00  0.00           C  
HETATM   33  C26 UNL     1      -8.817  -1.131  -0.093  1.00  0.00           C  
HETATM   34  C27 UNL     1      -7.732  -1.951  -0.245  1.00  0.00           C  
HETATM   35  O5  UNL     1      -7.930  -3.191  -0.467  1.00  0.00           O  
HETATM   36  N4  UNL     1      -6.464  -1.535  -0.173  1.00  0.00           N  
HETATM   37  C28 UNL     1      -5.223  -2.289  -0.310  1.00  0.00           C  
HETATM   38  C29 UNL     1     -10.212  -1.618  -0.194  1.00  0.00           C  
HETATM   39  O6  UNL     1     -11.080  -0.689  -0.826  1.00  0.00           O  
HETATM   40  C30 UNL     1     -10.788   0.650  -0.766  1.00  0.00           C  
HETATM   41  O7  UNL     1     -11.270   1.490  -1.520  1.00  0.00           O  
HETATM   42  C31 UNL     1      -9.822   1.066   0.298  1.00  0.00           C  
HETATM   43  O8  UNL     1     -10.433   0.611   1.501  1.00  0.00           O  
HETATM   44  C32 UNL     1      -9.662   2.532   0.312  1.00  0.00           C  
HETATM   45  C33 UNL     1      -8.840   3.020   1.453  1.00  0.00           C  
HETATM   46  H1  UNL     1      -1.330  -3.590  -2.261  1.00  0.00           H  
HETATM   47  H2  UNL     1      -2.499  -2.256  -2.577  1.00  0.00           H  
HETATM   48  H3  UNL     1      -3.080  -3.863  -2.154  1.00  0.00           H  
HETATM   49  H4  UNL     1      -1.249  -2.944  -0.049  1.00  0.00           H  
HETATM   50  H5  UNL     1      -2.912  -3.501   0.045  1.00  0.00           H  
HETATM   51  H6  UNL     1      -2.245   3.000   0.575  1.00  0.00           H  
HETATM   52  H7  UNL     1       0.129   2.776   0.474  1.00  0.00           H  
HETATM   53  H8  UNL     1       4.820   2.651   0.309  1.00  0.00           H  
HETATM   54  H9  UNL     1       5.081   1.613   1.739  1.00  0.00           H  
HETATM   55  H10 UNL     1       7.118   1.700   0.569  1.00  0.00           H  
HETATM   56  H11 UNL     1       6.352   1.722  -1.025  1.00  0.00           H  
HETATM   57  H12 UNL     1       6.144  -0.676   0.857  1.00  0.00           H  
HETATM   58  H13 UNL     1       7.788  -0.977  -1.601  1.00  0.00           H  
HETATM   59  H14 UNL     1       9.614  -1.539  -0.315  1.00  0.00           H  
HETATM   60  H15 UNL     1       8.721  -1.278   1.175  1.00  0.00           H  
HETATM   61  H16 UNL     1       9.058   1.074   1.137  1.00  0.00           H  
HETATM   62  H17 UNL     1       9.888   1.023  -0.495  1.00  0.00           H  
HETATM   63  H18 UNL     1      10.622  -0.351   2.110  1.00  0.00           H  
HETATM   64  H19 UNL     1      11.415   1.087   1.459  1.00  0.00           H  
HETATM   65  H20 UNL     1      11.482  -1.751   0.213  1.00  0.00           H  
HETATM   66  H21 UNL     1      12.751  -0.921   1.107  1.00  0.00           H  
HETATM   67  H22 UNL     1      12.117   1.917  -0.289  1.00  0.00           H  
HETATM   68  H23 UNL     1       5.507  -1.756  -1.372  1.00  0.00           H  
HETATM   69  H24 UNL     1       5.355  -0.032  -1.972  1.00  0.00           H  
HETATM   70  H25 UNL     1       3.254  -0.702  -1.060  1.00  0.00           H  
HETATM   71  H26 UNL     1       4.025  -1.307   0.499  1.00  0.00           H  
HETATM   72  H27 UNL     1      -0.148  -1.361  -0.246  1.00  0.00           H  
HETATM   73  H28 UNL     1      -7.081   1.685   0.394  1.00  0.00           H  
HETATM   74  H29 UNL     1      -5.115  -2.728  -1.313  1.00  0.00           H  
HETATM   75  H30 UNL     1      -5.082  -3.037   0.500  1.00  0.00           H  
HETATM   76  H31 UNL     1     -10.643  -1.969   0.753  1.00  0.00           H  
HETATM   77  H32 UNL     1     -10.170  -2.517  -0.886  1.00  0.00           H  
HETATM   78  H33 UNL     1      -9.820   0.013   1.995  1.00  0.00           H  
HETATM   79  H34 UNL     1      -9.259   2.915  -0.681  1.00  0.00           H  
HETATM   80  H35 UNL     1     -10.678   3.019   0.362  1.00  0.00           H  
HETATM   81  H36 UNL     1      -8.514   2.234   2.142  1.00  0.00           H  
HETATM   82  H37 UNL     1      -8.026   3.695   1.130  1.00  0.00           H  
HETATM   83  H38 UNL     1      -9.482   3.696   2.122  1.00  0.00           H  
CONECT    1    2   46   47   48
CONECT    2    3   49   50
CONECT    3    4    4   29
CONECT    4    5   37
CONECT    5    6    6   30
CONECT    6    7
CONECT    7    8    8   29
CONECT    8    9   51
CONECT    9   10   10   52
CONECT   10   11   28
CONECT   11   12
CONECT   12   13   13   14
CONECT   14   15   27
CONECT   15   16   53   54
CONECT   16   17   55   56
CONECT   17   18   26   57
CONECT   18   19   58
CONECT   19   20   59   60
CONECT   20   21   61   62
CONECT   21   22   63   64
CONECT   22   23   65   66
CONECT   23   24   24   25
CONECT   25   67
CONECT   26   27   68   69
CONECT   27   70   71
CONECT   28   29   29   72
CONECT   30   31   31   36
CONECT   31   32   73
CONECT   32   33   33   42
CONECT   33   34   38
CONECT   34   35   35   36
CONECT   36   37
CONECT   37   74   75
CONECT   38   39   76   77
CONECT   39   40
CONECT   40   41   41   42
CONECT   42   43   44
CONECT   43   78
CONECT   44   45   79   80
CONECT   45   81   82   83
END

HMDB0060661
     RDKit          3D
APC
 83 88  0  0  0  0  0  0  0  0999 V2000
   -2.2780   -3.1333   -1.9370 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2202   -2.7682   -0.4728 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8116   -1.4442   -0.2016 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1858   -1.2555   -0.1461 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7793   -0.0450    0.0803 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9491    0.9999    0.2538 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6137    0.8832    0.2121 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8131    2.0035    0.3898 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4383    1.8739    0.3341 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2021    0.6992    0.1119 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5370    0.4974    0.0405 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5892    1.2518    0.4527 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3185    2.3455    0.9917 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9212    0.7573    0.2451 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.0225    1.5873    0.6403 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3410    1.2271   -0.0199 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5131   -0.2380   -0.1322 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6728   -0.7932   -0.5833 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.8617   -0.7860    0.1373 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6299    0.4539    0.3932 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9301    0.1508    1.1560 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8750   -0.7378    0.4172 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3197   -0.1189   -0.8255 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9182   -0.7013   -1.7507 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.0741    1.2540   -1.0430 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3780   -0.6992   -1.0999 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1040   -0.5706   -0.3310 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6244   -0.4183   -0.0641 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9988   -0.3531   -0.0190 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2227   -0.2365    0.0590 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3032    0.6473    0.2208 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.6054    0.2439    0.1527 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.8169   -1.1314   -0.0935 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7322   -1.9512   -0.2446 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9299   -3.1912   -0.4673 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4639   -1.5349   -0.1731 N   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2229   -2.2889   -0.3097 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.2116   -1.6183   -0.1938 C   0  0  0  0  0  0  0  0  0  0  0  0
  -11.0795   -0.6886   -0.8259 O   0  0  0  0  0  0  0  0  0  0  0  0
  -10.7880    0.6504   -0.7660 C   0  0  0  0  0  0  0  0  0  0  0  0
  -11.2704    1.4902   -1.5199 O   0  0  0  0  0  0  0  0  0  0  0  0
   -9.8217    1.0659    0.2980 C   0  0  1  0  0  0  0  0  0  0  0  0
  -10.4332    0.6111    1.5008 O   0  0  0  0  0  0  0  0  0  0  0  0
   -9.6618    2.5322    0.3117 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.8399    3.0204    1.4533 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3299   -3.5895   -2.2611 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4989   -2.2560   -2.5770 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0795   -3.8626   -2.1544 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2493   -2.9437   -0.0491 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9118   -3.5009    0.0453 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2446    2.9999    0.5754 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1288    2.7760    0.4744 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8197    2.6510    0.3085 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0807    1.6132    1.7387 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1175    1.7000    0.5693 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3518    1.7220   -1.0254 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1440   -0.6759    0.8573 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7884   -0.9767   -1.6008 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.6139   -1.5394   -0.3154 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.7206   -1.2782    1.1749 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.0582    1.0742    1.1368 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.8880    1.0226   -0.4952 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.6218   -0.3506    2.1101 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.4154    1.0869    1.4588 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.4815   -1.7505    0.2126 H   0  0  0  0  0  0  0  0  0  0  0  0
   12.7514   -0.9215    1.1070 H   0  0  0  0  0  0  0  0  0  0  0  0
   12.1172    1.9168   -0.2893 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5066   -1.7560   -1.3720 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3552   -0.0320   -1.9724 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2538   -0.7023   -1.0602 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0252   -1.3075    0.4991 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1481   -1.3612   -0.2461 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0807    1.6854    0.3936 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1152   -2.7285   -1.3134 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0817   -3.0370    0.5002 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.6428   -1.9693    0.7532 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.1696   -2.5166   -0.8865 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.8200    0.0133    1.9949 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.2590    2.9154   -0.6814 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.6780    3.0194    0.3622 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5143    2.2341    2.1423 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0263    3.6953    1.1298 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.4823    3.6961    2.1224 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
 12 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  2  0
 23 25  1  0
 17 26  1  0
 26 27  1  0
 10 28  1  0
 28 29  2  0
  5 30  1  0
 30 31  2  0
 31 32  1  0
 32 33  2  0
 33 34  1  0
 34 35  2  0
 34 36  1  0
 36 37  1  0
 33 38  1  0
 38 39  1  0
 39 40  1  0
 40 41  2  0
 40 42  1  0
 42 43  1  1
 42 44  1  0
 44 45  1  0
 29  3  1  0
 36 30  1  0
 37  4  1  0
 29  7  1  0
 42 32  1  0
 27 14  1  0
  1 46  1  0
  1 47  1  0
  1 48  1  0
  2 49  1  0
  2 50  1  0
  8 51  1  0
  9 52  1  0
 15 53  1  0
 15 54  1  0
 16 55  1  0
 16 56  1  0
 17 57  1  0
 18 58  1  0
 19 59  1  0
 19 60  1  0
 20 61  1  0
 20 62  1  0
 21 63  1  0
 21 64  1  0
 22 65  1  0
 22 66  1  0
 25 67  1  0
 26 68  1  0
 26 69  1  0
 27 70  1  0
 27 71  1  0
 28 72  1  0
 31 73  1  0
 37 74  1  0
 37 75  1  0
 38 76  1  0
 38 77  1  0
 43 78  1  0
 44 79  1  0
 44 80  1  0
 45 81  1  0
 45 82  1  0
 45 83  1  0
M  END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
1,2-Propanedione	HMDB
2-Ketopropionaldehyde	HMDB
2-Oxopropanal	HMDB
2-Oxopropionaldehyde	HMDB
Acetylformaldehyde	HMDB
Acetylformyl	HMDB
alpha-Ketopropionaldehyde	HMDB
CH3COCHO	HMDB
Pyruvic aldehyde	HMDB
a-Ketopropionaldehyde	HMDB
Α-ketopropionaldehyde	HMDB
1-Ketopropionaldehyde	HMDB
2-Keto propionaldehyde	HMDB
2-oxo-Propionaldehyde	HMDB
Ketopropionaldehyde	HMDB
Methylglyoxal	HMDB
Propanedione	HMDB
Propanolone	HMDB
Pyroracemic aldehyde	HMDB
Aldehyde, pyruvic	HMDB
Oxopropanal	HMDB
APC CPD	HMDB
7-Ethyl-10-(4-N-(5-aminopentanoic acid)-1-piperidino)carbonyloxycamptothecin	HMDB

Chemical Formula

C₃₃H₃₈N₄O₈

Average Molecular Weight

618.6768

Monoisotopic Molecular Weight

618.268964212

IUPAC Name

5-{[1-({[(19S)-10,19-diethyl-19-hydroxy-14,18-dioxo-17-oxa-3,13-diazapentacyclo[11.8.0.0²,¹¹.0⁴,⁹.0¹⁵,²⁰]henicosa-1(21),2,4,6,8,10,15(20)-heptaen-7-yl]oxy}carbonyl)piperidin-4-yl]amino}pentanoic acid

Traditional Name

CAS Registry Number

Not Available

SMILES

CCC1=C2CN3C(=CC4=C(COC(=O)[C@]4(O)CC)C3=O)C2=NC2=CC=C(OC(=O)N3CCC(CC3)NCCCCC(O)=O)C=C12

InChI Identifier

InChI=1S/C33H38N4O8/c1-3-21-22-15-20(45-32(42)36-13-10-19(11-14-36)34-12-6-5-7-28(38)39)8-9-26(22)35-29-23(21)17-37-27(29)16-25-24(30(37)40)18-44-31(41)33(25,43)4-2/h8-9,15-16,19,34,43H,3-7,10-14,17-18H2,1-2H3,(H,38,39)/t33-/m0/s1

InChI Key

BSVVZICJFYZDJJ-XIFFEERXSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as camptothecins. These are heterocyclic compounds comprising a planar pentacyclic ring structure, that includes a pyrrolo[3,4-beta]-quinoline moiety (rings A, B and C), conjugated pyridone moiety (ring D) and one chiral center at position 20 within the alpha-hydroxy lactone ring with (S) configuration (the E-ring).

Kingdom

Organic compounds

Super Class

Alkaloids and derivatives

Class

Camptothecins

Sub Class

Not Available

Direct Parent

Camptothecins

Alternative Parents

Substituents

Camptothecin
Delta amino acid or derivatives
Pyranopyridine
Quinoline
Piperidinecarboxylic acid
4-aminopiperidine
Pyridinone
Piperidine
Dicarboxylic acid or derivatives
Pyridine
Benzenoid
Heteroaromatic compound
Carbamic acid ester
Tertiary alcohol
Carbonic acid derivative
Lactone
Lactam
Amino acid
Carboxylic acid ester
Amino acid or derivatives
Carboxylic acid derivative
Carboxylic acid
Secondary aliphatic amine
Oxacycle
Azacycle
Organoheterocyclic compound
Secondary amine
Hydrocarbon derivative
Amine
Organic oxide
Alcohol
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Carbonyl group
Organonitrogen compound
Organooxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

pyranoindolizinoquinoline (CHEBI:80551 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (HMDB: HMDB0060661)

Organ

Liver (HMDB: HMDB0060661)
Kidney (HMDB: HMDB0060661)

Excreta

Biofluid or Excreta

Urine (HMDB: HMDB0060661)

Source

Endogenous

Endogenous (HMDB: HMDB0060661)

Process

Naturally occurring process

Biological process

Biochemical pathway

Drug action pathway

Irinotecan Action Pathway (PathBank: SMP0000433)

Metabolic pathway

Irinotecan Metabolism Pathway (PathBank: SMP0000600)

Role

Not Available

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.048 g/L	ALOGPS
logP	2.32	ALOGPS
logP	-0.48	ChemAxon
logS	-4.1	ALOGPS
pKa (Strongest Acidic)	4.66	ChemAxon
pKa (Strongest Basic)	10.58	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	158.6 Å²	ChemAxon
Rotatable Bond Count	10	ChemAxon
Refractivity	164.03 m³·mol⁻¹	ChemAxon
Polarizability	66.5 Å³	ChemAxon
Number of Rings	6	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	239.657	31661259
DarkChem	[M-H]-	236.111	31661259
DeepCCS	[M-2H]-	284.973	30932474
DeepCCS	[M+Na]+	259.405	30932474
AllCCS	[M+H]+	237.7	32859911
AllCCS	[M+H-H2O]+	236.8	32859911
AllCCS	[M+NH4]+	238.6	32859911
AllCCS	[M+Na]+	238.8	32859911
AllCCS	[M-H]-	227.2	32859911
AllCCS	[M+Na-2H]-	230.5	32859911
AllCCS	[M+HCOO]-	234.1	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
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.	5.21 minutes	32390414
Predicted by Siyang on May 30, 2022	11.4554 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	4.26 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	1835.6 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	153.6 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	199.0 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	160.2 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	117.6 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	348.3 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	411.9 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	467.6 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	769.1 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	499.0 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	1452.5 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	281.5 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	305.1 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	375.2 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	262.6 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	85.4 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
APC	CCC1=C2CN3C(=CC4=C(COC(=O)[C@]4(O)CC)C3=O)C2=NC2=CC=C(OC(=O)N3CCC(CC3)NCCCCC(O)=O)C=C12	5461.0	Standard polar	33892256
APC	CCC1=C2CN3C(=CC4=C(COC(=O)[C@]4(O)CC)C3=O)C2=NC2=CC=C(OC(=O)N3CCC(CC3)NCCCCC(O)=O)C=C12	4652.8	Standard non polar	33892256
APC	CCC1=C2CN3C(=CC4=C(COC(=O)[C@]4(O)CC)C3=O)C2=NC2=CC=C(OC(=O)N3CCC(CC3)NCCCCC(O)=O)C=C12	5625.5	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
APC,1TMS,isomer #1	CCC1=C2CN3C(=CC4=C(COC(=O)[C@@]4(CC)O[Si](C)(C)C)C3=O)C2=NC2=CC=C(OC(=O)N3CCC(NCCCCC(=O)O)CC3)C=C12	5237.2	Semi standard non polar	33892256
APC,1TMS,isomer #2	CCC1=C2CN3C(=CC4=C(COC(=O)[C@]4(O)CC)C3=O)C2=NC2=CC=C(OC(=O)N3CCC(NCCCCC(=O)O[Si](C)(C)C)CC3)C=C12	5168.0	Semi standard non polar	33892256
APC,1TMS,isomer #3	CCC1=C2CN3C(=CC4=C(COC(=O)[C@]4(O)CC)C3=O)C2=NC2=CC=C(OC(=O)N3CCC(N(CCCCC(=O)O)[Si](C)(C)C)CC3)C=C12	5266.4	Semi standard non polar	33892256
APC,2TMS,isomer #1	CCC1=C2CN3C(=CC4=C(COC(=O)[C@@]4(CC)O[Si](C)(C)C)C3=O)C2=NC2=CC=C(OC(=O)N3CCC(NCCCCC(=O)O[Si](C)(C)C)CC3)C=C12	5074.6	Semi standard non polar	33892256
APC,2TMS,isomer #2	CCC1=C2CN3C(=CC4=C(COC(=O)[C@@]4(CC)O[Si](C)(C)C)C3=O)C2=NC2=CC=C(OC(=O)N3CCC(N(CCCCC(=O)O)[Si](C)(C)C)CC3)C=C12	5179.6	Semi standard non polar	33892256
APC,2TMS,isomer #3	CCC1=C2CN3C(=CC4=C(COC(=O)[C@]4(O)CC)C3=O)C2=NC2=CC=C(OC(=O)N3CCC(N(CCCCC(=O)O[Si](C)(C)C)[Si](C)(C)C)CC3)C=C12	5112.4	Semi standard non polar	33892256
APC,3TMS,isomer #1	CCC1=C2CN3C(=CC4=C(COC(=O)[C@@]4(CC)O[Si](C)(C)C)C3=O)C2=NC2=CC=C(OC(=O)N3CCC(N(CCCCC(=O)O[Si](C)(C)C)[Si](C)(C)C)CC3)C=C12	5027.0	Semi standard non polar	33892256
APC,3TMS,isomer #1	CCC1=C2CN3C(=CC4=C(COC(=O)[C@@]4(CC)O[Si](C)(C)C)C3=O)C2=NC2=CC=C(OC(=O)N3CCC(N(CCCCC(=O)O[Si](C)(C)C)[Si](C)(C)C)CC3)C=C12	5009.7	Standard non polar	33892256
APC,3TMS,isomer #1	CCC1=C2CN3C(=CC4=C(COC(=O)[C@@]4(CC)O[Si](C)(C)C)C3=O)C2=NC2=CC=C(OC(=O)N3CCC(N(CCCCC(=O)O[Si](C)(C)C)[Si](C)(C)C)CC3)C=C12	6557.1	Standard polar	33892256
APC,1TBDMS,isomer #1	CCC1=C2CN3C(=CC4=C(COC(=O)[C@@]4(CC)O[Si](C)(C)C(C)(C)C)C3=O)C2=NC2=CC=C(OC(=O)N3CCC(NCCCCC(=O)O)CC3)C=C12	5426.4	Semi standard non polar	33892256
APC,1TBDMS,isomer #2	CCC1=C2CN3C(=CC4=C(COC(=O)[C@]4(O)CC)C3=O)C2=NC2=CC=C(OC(=O)N3CCC(NCCCCC(=O)O[Si](C)(C)C(C)(C)C)CC3)C=C12	5387.8	Semi standard non polar	33892256
APC,1TBDMS,isomer #3	CCC1=C2CN3C(=CC4=C(COC(=O)[C@]4(O)CC)C3=O)C2=NC2=CC=C(OC(=O)N3CCC(N(CCCCC(=O)O)[Si](C)(C)C(C)(C)C)CC3)C=C12	5465.5	Semi standard non polar	33892256
APC,2TBDMS,isomer #1	CCC1=C2CN3C(=CC4=C(COC(=O)[C@@]4(CC)O[Si](C)(C)C(C)(C)C)C3=O)C2=NC2=CC=C(OC(=O)N3CCC(NCCCCC(=O)O[Si](C)(C)C(C)(C)C)CC3)C=C12	5435.7	Semi standard non polar	33892256
APC,2TBDMS,isomer #2	CCC1=C2CN3C(=CC4=C(COC(=O)[C@@]4(CC)O[Si](C)(C)C(C)(C)C)C3=O)C2=NC2=CC=C(OC(=O)N3CCC(N(CCCCC(=O)O)[Si](C)(C)C(C)(C)C)CC3)C=C12	5538.6	Semi standard non polar	33892256
APC,2TBDMS,isomer #3	CCC1=C2CN3C(=CC4=C(COC(=O)[C@]4(O)CC)C3=O)C2=NC2=CC=C(OC(=O)N3CCC(N(CCCCC(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)CC3)C=C12	5497.4	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - APC GC-MS (1 TMS) - 70eV, Positive	splash10-00ba-3200019000-0f121ba3b50d1e965587	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - APC GC-MS (TMS_1_2) - 70eV, Positive	Not Available	2021-10-16	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - APC GC-MS (TMS_1_3) - 70eV, Positive	Not Available	2021-10-16	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - APC GC-MS (TMS_2_1) - 70eV, Positive	Not Available	2021-10-16	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - APC GC-MS (TMS_2_2) - 70eV, Positive	Not Available	2021-10-16	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - APC GC-MS (TMS_2_3) - 70eV, Positive	Not Available	2021-10-16	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - APC GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-10-16	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - APC GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	2021-10-16	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - APC GC-MS (TBDMS_1_3) - 70eV, Positive	Not Available	2021-10-16	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - APC GC-MS (TBDMS_2_1) - 70eV, Positive	Not Available	2021-10-16	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - APC GC-MS (TBDMS_2_2) - 70eV, Positive	Not Available	2021-10-16	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - APC GC-MS (TBDMS_2_3) - 70eV, Positive	Not Available	2021-10-16	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - APC GC-MS ("APC,1TMS,#1" TMS) - 70eV, Positive	Not Available	2021-11-02	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - APC 10V, Positive-QTOF	splash10-0udi-0341049000-7513ad575f77fd51def9	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - APC 20V, Positive-QTOF	splash10-0ugi-2942031000-d25ec79870cfe710f25a	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - APC 40V, Positive-QTOF	splash10-0udi-5940000000-188d67903155f2e16c88	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - APC 10V, Negative-QTOF	splash10-01b9-0141198000-2caccacf3add053c51c4	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - APC 20V, Negative-QTOF	splash10-00vm-0454192000-e9d5fd01fd23b2c56742	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - APC 40V, Negative-QTOF	splash10-0037-3894020000-46ebd1df6ec7bd8c5fc4	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - APC 10V, Positive-QTOF	splash10-0gb9-0000009000-492e35b52563dcd8aa25	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - APC 20V, Positive-QTOF	splash10-0udi-0000089000-6495393de2962bd71a21	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - APC 40V, Positive-QTOF	splash10-0900-9218411000-cccb21d7ce03f6381137	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - APC 10V, Negative-QTOF	splash10-014i-0002059000-981e8115208bea24955f	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - APC 20V, Negative-QTOF	splash10-05tb-0002091000-df410fa1c698619938fb	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - APC 40V, Negative-QTOF	splash10-014l-2734297000-26884603c52a800389f2	2021-10-12	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Blood
Urine

Tissue Locations

Kidney
Liver

Pathways

Name	SMPDB/PathBank	KEGG
Irinotecan Action Pathway		Not Available
Irinotecan Metabolism Pathway		Not Available

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Expected but not Quantified	Not Quantified	Not Available	Not Available	Normal	Not Available	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Normal	Not Available	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

Not Available

BiGG ID

Wikipedia Link

METLIN ID

PubChem Compound

PDB ID

Not Available

ChEBI ID

17158

Food Biomarker Ontology

Not Available

VMH ID

MTHGXL

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Not Available

Showing metabocard for APC (HMDB0060661)

MOL for HMDB0060661 (APC)

3D MOL for HMDB0060661 (APC)

3D SDF for HMDB0060661 (APC)

3D-SDF for HMDB0060661 (APC)

PDB for HMDB0060661 (APC)

3D PDB for HMDB0060661 (APC)

SMILES for HMDB0060661 (APC)

INCHI for HMDB0060661 (APC)

Structure for HMDB0060661 (APC)

3D Structure for HMDB0060661 (APC)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra