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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-11 01:56:35 UTC

Update Date

2021-09-26 22:58:51 UTC

HMDB ID

HMDB0248528

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Apovincaminic acid

Description

Apovincaminic acid, also known as apovincaminate, belongs to the class of organic compounds known as eburnan-type alkaloids. These are alkaloids with a structure based on the eburnan skeleton, that arises from rearrangement of the aspidospermidine ring system, involving migration of C-21 from C-7 to C-2, fission of the 2,16-bond, and attachment of C-16 to N-1. Based on a literature review a significant number of articles have been published on Apovincaminic acid. This compound has been identified in human blood as reported by (PMID: 31557052 ). Apovincaminic acid is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically Apovincaminic acid is part of the human exposome. The exposome can be defined as the collection of all the exposures of an individual in a lifetime and how those exposures relate to health. An individual's exposure begins before birth and includes insults from environmental and occupational sources.

Structure

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

HMDB0248528
     RDKit          3D
Apovincaminic acid
 46 50  0  0  0  0  0  0  0  0999 V2000
   -2.8231    1.6777    1.7732 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8327    0.5611    1.6015 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6145    0.3486    0.0979 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0976    1.6085   -0.4231 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2160    1.8842   -0.5232 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5746    3.1628   -1.0359 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6789    3.6224   -1.2376 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4743    4.0607   -1.3716 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1581    0.8516   -0.2788 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.7008   -0.3751    0.0126 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6984   -1.2288    0.3525 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8641   -0.4759    0.2610 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1667   -0.8185    0.5000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1308    0.1352    0.3462 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8294    1.4098   -0.0359 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4860    1.7361   -0.2747 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4885    0.8114   -0.1341 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3690   -2.6167    0.7082 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0314   -2.9718    0.3369 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0113   -1.9326    0.6760 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2696   -2.4269    0.1363 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3436   -1.4420   -0.0573 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9526   -0.0543   -0.4763 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6917   -0.7788   -0.1525 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9833    2.2914    0.8674 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5724    2.3243    2.6620 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8462    1.2725    2.0281 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8727    0.8861    2.0310 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2294   -0.3589    2.0768 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7881    2.3627   -0.7519 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4922    4.4846   -2.3027 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3970   -1.8365    0.8045 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1540   -0.1159    0.5285 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6226    2.1555   -0.1515 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3352    2.7524   -0.5449 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0463   -3.2880    0.1409 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5772   -2.8397    1.7913 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3182   -3.9498    0.7669 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0645   -3.0329   -0.7901 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0570   -3.0461   -0.7846 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6266   -3.1930    0.8860 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0278   -1.8306   -0.8642 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0000   -1.3741    0.8534 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7105    0.6534   -0.0932 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8968    0.0393   -1.5726 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8653   -1.1056   -1.2251 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  6  8  1  0
  5  9  1  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
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 15 16  1  0
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 11 18  1  0
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 23  3  1  0
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 17  9  1  0
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 17 12  1  0
  1 25  1  0
  1 26  1  0
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 21 40  1  0
 21 41  1  0
 22 42  1  0
 22 43  1  0
 23 44  1  0
 23 45  1  0
 24 46  1  0
M  END


  Mrv1652309112103562D          

 24 28  0  0  0  0            999 V2000
    4.5785    4.2719    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7548    4.2248    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3838    3.4879    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2075    3.5350    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6601    2.8453    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2891    2.1084    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4655    2.0613    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.0128    2.7510    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1892    2.7039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8182    1.9670    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2708    1.2772    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0945    1.3244    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9014    2.3522    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1682    1.9741    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5259    2.4201    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4867    3.2441    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2466    3.6222    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9407    3.1762    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7365    3.3936    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.1075    4.1305    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9312    4.1776    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6548    4.8202    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0258    5.5571    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8312    4.7730    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  3  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
  7 12  1  0  0  0  0
 10 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 13 18  1  0  0  0  0
 18 19  1  0  0  0  0
  9 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
  3 21  1  0  0  0  0
 20 22  1  0  0  0  0
 22 23  2  0  0  0  0
 22 24  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0248528

> <DATABASE_NAME>
hmdb

> <SMILES>
CCC12CCCN3CCC4=C(C13)N(C1=CC=CC=C41)C(=C2)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C20H22N2O2/c1-2-20-9-5-10-21-11-8-14-13-6-3-4-7-15(13)22(17(14)18(20)21)16(12-20)19(23)24/h3-4,6-7,12,18H,2,5,8-11H2,1H3,(H,23,24)

> <INCHI_KEY>
ZFCQLDAGNBFMJQ-UHFFFAOYSA-N

> <FORMULA>
C20H22N2O2

> <MOLECULAR_WEIGHT>
322.408

> <EXACT_MASS>
322.168127956

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
46

> <JCHEM_AVERAGE_POLARIZABILITY>
35.897956488680805

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
15-ethyl-1,11-diazapentacyclo[9.6.2.0^{2,7}.0^{8,18}.0^{15,19}]nonadeca-2,4,6,8(18),16-pentaene-17-carboxylic acid

> <ALOGPS_LOGP>
3.50

> <JCHEM_LOGP>
0.7760789292200514

> <ALOGPS_LOGS>
-3.57

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.010070599553664

> <JCHEM_PKA_STRONGEST_BASIC>
7.071100477832654

> <JCHEM_POLAR_SURFACE_AREA>
45.47

> <JCHEM_REFRACTIVITY>
94.7207

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
8.71e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
15-ethyl-1,11-diazapentacyclo[9.6.2.0^{2,7}.0^{8,18}.0^{15,19}]nonadeca-2,4,6,8(18),16-pentaene-17-carboxylic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0248528
     RDKit          3D
Apovincaminic acid
 46 50  0  0  0  0  0  0  0  0999 V2000
   -2.8231    1.6777    1.7732 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8327    0.5611    1.6015 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6145    0.3486    0.0979 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0976    1.6085   -0.4231 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2160    1.8842   -0.5232 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5746    3.1628   -1.0359 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6789    3.6224   -1.2376 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4743    4.0607   -1.3716 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1581    0.8516   -0.2788 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.7008   -0.3751    0.0126 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6984   -1.2288    0.3525 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8641   -0.4759    0.2610 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1667   -0.8185    0.5000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1308    0.1352    0.3462 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8294    1.4098   -0.0359 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4860    1.7361   -0.2747 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4885    0.8114   -0.1341 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3690   -2.6167    0.7082 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0314   -2.9718    0.3369 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0113   -1.9326    0.6760 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2696   -2.4269    0.1363 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3436   -1.4420   -0.0573 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9526   -0.0543   -0.4763 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6917   -0.7788   -0.1525 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9833    2.2914    0.8674 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5724    2.3243    2.6620 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8462    1.2725    2.0281 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8727    0.8861    2.0310 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2294   -0.3589    2.0768 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7881    2.3627   -0.7519 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4922    4.4846   -2.3027 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3970   -1.8365    0.8045 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1540   -0.1159    0.5285 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6226    2.1555   -0.1515 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3352    2.7524   -0.5449 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0463   -3.2880    0.1409 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5772   -2.8397    1.7913 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3182   -3.9498    0.7669 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0645   -3.0329   -0.7901 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0570   -3.0461   -0.7846 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6266   -3.1930    0.8860 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0278   -1.8306   -0.8642 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0000   -1.3741    0.8534 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7105    0.6534   -0.0932 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8968    0.0393   -1.5726 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8653   -1.1056   -1.2251 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  6  8  1  0
  5  9  1  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 11 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 20 24  1  0
 23  3  1  0
 24  3  1  0
 17  9  1  0
 24 10  1  0
 17 12  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
  2 28  1  0
  2 29  1  0
  4 30  1  0
  8 31  1  0
 13 32  1  0
 14 33  1  0
 15 34  1  0
 16 35  1  0
 18 36  1  0
 18 37  1  0
 19 38  1  0
 19 39  1  0
 21 40  1  0
 21 41  1  0
 22 42  1  0
 22 43  1  0
 23 44  1  0
 23 45  1  0
 24 46  1  0
M  END

HEADER    PROTEIN                                 11-SEP-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   11-SEP-21         0                                  
HETATM    1  C   UNK     0       8.546   7.974   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       7.009   7.886   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       6.316   6.511   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       7.854   6.599   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       8.699   5.311   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       8.006   3.936   0.000  0.00  0.00           C+0
HETATM    7  N   UNK     0       6.469   3.848   0.000  0.00  0.00           N+0
HETATM    8  C   UNK     0       5.624   5.135   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.086   5.047   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       3.394   3.672   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.239   2.384   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       5.776   2.472   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.683   4.391   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       0.314   3.685   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -0.982   4.517   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -0.908   6.056   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       0.460   6.761   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       1.756   5.929   0.000  0.00  0.00           C+0
HETATM   19  N   UNK     0       3.241   6.335   0.000  0.00  0.00           N+0
HETATM   20  C   UNK     0       3.934   7.710   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       5.471   7.798   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       3.089   8.998   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       3.782  10.373   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0       1.552   8.910   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    8   21                                             
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8   12                                                  
CONECT    8    7    3    9                                                  
CONECT    9    8   10   19                                                  
CONECT   10    9   11   13                                                  
CONECT   11   10   12                                                       
CONECT   12   11    7                                                       
CONECT   13   10   14   18                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   13   19                                                  
CONECT   19   18    9   20                                                  
CONECT   20   19   21   22                                                  
CONECT   21   20    3                                                       
CONECT   22   20   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22                                                            
MASTER        0    0    0    0    0    0    0    0   24    0   56    0
END

COMPND    HMDB0248528
HETATM    1  C1  UNL     1      -2.823   1.678   1.773  1.00  0.00           C  
HETATM    2  C2  UNL     1      -1.833   0.561   1.601  1.00  0.00           C  
HETATM    3  C3  UNL     1      -1.615   0.349   0.098  1.00  0.00           C  
HETATM    4  C4  UNL     1      -1.098   1.608  -0.423  1.00  0.00           C  
HETATM    5  C5  UNL     1       0.216   1.884  -0.523  1.00  0.00           C  
HETATM    6  C6  UNL     1       0.575   3.163  -1.036  1.00  0.00           C  
HETATM    7  O1  UNL     1       1.679   3.622  -1.238  1.00  0.00           O  
HETATM    8  O2  UNL     1      -0.474   4.061  -1.372  1.00  0.00           O  
HETATM    9  N1  UNL     1       1.158   0.852  -0.279  1.00  0.00           N  
HETATM   10  C7  UNL     1       0.701  -0.375   0.013  1.00  0.00           C  
HETATM   11  C8  UNL     1       1.698  -1.229   0.352  1.00  0.00           C  
HETATM   12  C9  UNL     1       2.864  -0.476   0.261  1.00  0.00           C  
HETATM   13  C10 UNL     1       4.167  -0.818   0.500  1.00  0.00           C  
HETATM   14  C11 UNL     1       5.131   0.135   0.346  1.00  0.00           C  
HETATM   15  C12 UNL     1       4.829   1.410  -0.036  1.00  0.00           C  
HETATM   16  C13 UNL     1       3.486   1.736  -0.275  1.00  0.00           C  
HETATM   17  C14 UNL     1       2.489   0.811  -0.134  1.00  0.00           C  
HETATM   18  C15 UNL     1       1.369  -2.617   0.708  1.00  0.00           C  
HETATM   19  C16 UNL     1      -0.031  -2.972   0.337  1.00  0.00           C  
HETATM   20  N2  UNL     1      -1.011  -1.933   0.676  1.00  0.00           N  
HETATM   21  C17 UNL     1      -2.270  -2.427   0.136  1.00  0.00           C  
HETATM   22  C18 UNL     1      -3.344  -1.442  -0.057  1.00  0.00           C  
HETATM   23  C19 UNL     1      -2.953  -0.054  -0.476  1.00  0.00           C  
HETATM   24  C20 UNL     1      -0.692  -0.779  -0.153  1.00  0.00           C  
HETATM   25  H1  UNL     1      -2.983   2.291   0.867  1.00  0.00           H  
HETATM   26  H2  UNL     1      -2.572   2.324   2.662  1.00  0.00           H  
HETATM   27  H3  UNL     1      -3.846   1.272   2.028  1.00  0.00           H  
HETATM   28  H4  UNL     1      -0.873   0.886   2.031  1.00  0.00           H  
HETATM   29  H5  UNL     1      -2.229  -0.359   2.077  1.00  0.00           H  
HETATM   30  H6  UNL     1      -1.788   2.363  -0.752  1.00  0.00           H  
HETATM   31  H7  UNL     1      -0.492   4.485  -2.303  1.00  0.00           H  
HETATM   32  H8  UNL     1       4.397  -1.837   0.805  1.00  0.00           H  
HETATM   33  H9  UNL     1       6.154  -0.116   0.529  1.00  0.00           H  
HETATM   34  H10 UNL     1       5.623   2.155  -0.152  1.00  0.00           H  
HETATM   35  H11 UNL     1       3.335   2.752  -0.545  1.00  0.00           H  
HETATM   36  H12 UNL     1       2.046  -3.288   0.141  1.00  0.00           H  
HETATM   37  H13 UNL     1       1.577  -2.840   1.791  1.00  0.00           H  
HETATM   38  H14 UNL     1      -0.318  -3.950   0.767  1.00  0.00           H  
HETATM   39  H15 UNL     1      -0.064  -3.033  -0.790  1.00  0.00           H  
HETATM   40  H16 UNL     1      -2.057  -3.046  -0.785  1.00  0.00           H  
HETATM   41  H17 UNL     1      -2.627  -3.193   0.886  1.00  0.00           H  
HETATM   42  H18 UNL     1      -4.028  -1.831  -0.864  1.00  0.00           H  
HETATM   43  H19 UNL     1      -4.000  -1.374   0.853  1.00  0.00           H  
HETATM   44  H20 UNL     1      -3.710   0.653  -0.093  1.00  0.00           H  
HETATM   45  H21 UNL     1      -2.897   0.039  -1.573  1.00  0.00           H  
HETATM   46  H22 UNL     1      -0.865  -1.106  -1.225  1.00  0.00           H  
CONECT    1    2   25   26   27
CONECT    2    3   28   29
CONECT    3    4   23   24
CONECT    4    5    5   30
CONECT    5    6    9
CONECT    6    7    7    8
CONECT    8   31
CONECT    9   10   17
CONECT   10   11   11   24
CONECT   11   12   18
CONECT   12   13   13   17
CONECT   13   14   32
CONECT   14   15   15   33
CONECT   15   16   34
CONECT   16   17   17   35
CONECT   18   19   36   37
CONECT   19   20   38   39
CONECT   20   21   24
CONECT   21   22   40   41
CONECT   22   23   42   43
CONECT   23   44   45
CONECT   24   46
END

HMDB0248528
     RDKit          3D
Apovincaminic acid
 46 50  0  0  0  0  0  0  0  0999 V2000
   -2.8231    1.6777    1.7732 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8327    0.5611    1.6015 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6145    0.3486    0.0979 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0976    1.6085   -0.4231 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2160    1.8842   -0.5232 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5746    3.1628   -1.0359 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6789    3.6224   -1.2376 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4743    4.0607   -1.3716 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1581    0.8516   -0.2788 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.7008   -0.3751    0.0126 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6984   -1.2288    0.3525 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8641   -0.4759    0.2610 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1667   -0.8185    0.5000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1308    0.1352    0.3462 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8294    1.4098   -0.0359 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4860    1.7361   -0.2747 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4885    0.8114   -0.1341 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3690   -2.6167    0.7082 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0314   -2.9718    0.3369 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0113   -1.9326    0.6760 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2696   -2.4269    0.1363 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3436   -1.4420   -0.0573 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9526   -0.0543   -0.4763 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6917   -0.7788   -0.1525 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9833    2.2914    0.8674 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5724    2.3243    2.6620 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8462    1.2725    2.0281 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8727    0.8861    2.0310 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2294   -0.3589    2.0768 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7881    2.3627   -0.7519 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4922    4.4846   -2.3027 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3970   -1.8365    0.8045 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1540   -0.1159    0.5285 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6226    2.1555   -0.1515 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3352    2.7524   -0.5449 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0463   -3.2880    0.1409 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5772   -2.8397    1.7913 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3182   -3.9498    0.7669 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0645   -3.0329   -0.7901 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0570   -3.0461   -0.7846 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6266   -3.1930    0.8860 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0278   -1.8306   -0.8642 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0000   -1.3741    0.8534 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7105    0.6534   -0.0932 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8968    0.0393   -1.5726 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8653   -1.1056   -1.2251 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  6  8  1  0
  5  9  1  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 11 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 20 24  1  0
 23  3  1  0
 24  3  1  0
 17  9  1  0
 24 10  1  0
 17 12  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
  2 28  1  0
  2 29  1  0
  4 30  1  0
  8 31  1  0
 13 32  1  0
 14 33  1  0
 15 34  1  0
 16 35  1  0
 18 36  1  0
 18 37  1  0
 19 38  1  0
 19 39  1  0
 21 40  1  0
 21 41  1  0
 22 42  1  0
 22 43  1  0
 23 44  1  0
 23 45  1  0
 24 46  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Apovincaminate	Generator

Chemical Formula

C₂₀H₂₂N₂O₂

Average Molecular Weight

322.408

Monoisotopic Molecular Weight

322.168127956

IUPAC Name

15-ethyl-1,11-diazapentacyclo[9.6.2.0^{2,7}.0^{8,18}.0^{15,19}]nonadeca-2,4,6,8(18),16-pentaene-17-carboxylic acid

Traditional Name

15-ethyl-1,11-diazapentacyclo[9.6.2.0^{2,7}.0^{8,18}.0^{15,19}]nonadeca-2,4,6,8(18),16-pentaene-17-carboxylic acid

CAS Registry Number

Not Available

SMILES

CCC12CCCN3CCC4=C(C13)N(C1=CC=CC=C41)C(=C2)C(O)=O

InChI Identifier

InChI=1S/C20H22N2O2/c1-2-20-9-5-10-21-11-8-14-13-6-3-4-7-15(13)22(17(14)18(20)21)16(12-20)19(23)24/h3-4,6-7,12,18H,2,5,8-11H2,1H3,(H,23,24)

InChI Key

ZFCQLDAGNBFMJQ-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as eburnan-type alkaloids. These are alkaloids with a structure based on the eburnan skeleton, that arises from rearrangement of the aspidospermidine ring system, involving migration of C-21 from C-7 to C-2, fission of the 2,16-bond, and attachment of C-16 to N-1.

Kingdom

Organic compounds

Super Class

Alkaloids and derivatives

Class

Eburnan-type alkaloids

Sub Class

Not Available

Direct Parent

Eburnan-type alkaloids

Alternative Parents

Substituents

Eburna alkaloid
Indolo[3,2-1de][1,5]naphthyridine
Beta-carboline
Pyridoindole
Alpha-amino acid or derivatives
3-alkylindole
Naphthyridine
Indole
Indole or derivatives
Aralkylamine
Benzenoid
Piperidine
Heteroaromatic compound
Pyrrole
Amino acid
Amino acid or derivatives
Tertiary aliphatic amine
Tertiary amine
Azacycle
Organoheterocyclic compound
Carboxylic acid derivative
Carboxylic acid
Monocarboxylic acid or derivatives
Organic nitrogen compound
Organic oxide
Carbonyl group
Organic oxygen compound
Amine
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 31557052)

Source

Exogenous

Exogenous (PMID: 31557052)

Process

Not Available

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
logP	3.5	ALOGPS
logP	0.78	ChemAxon
logS	-3.6	ALOGPS
pKa (Strongest Acidic)	4.01	ChemAxon
pKa (Strongest Basic)	7.07	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	45.47 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	94.72 m³·mol⁻¹	ChemAxon
Polarizability	35.9 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DeepCCS	[M-2H]-	214.143	30932474
DeepCCS	[M+Na]+	190.138	30932474
AllCCS	[M+H]+	177.4	32859911
AllCCS	[M+H-H2O]+	174.4	32859911
AllCCS	[M+NH4]+	180.2	32859911
AllCCS	[M+Na]+	181.0	32859911
AllCCS	[M-H]-	182.3	32859911
AllCCS	[M+Na-2H]-	181.7	32859911
AllCCS	[M+HCOO]-	181.2	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Predicted by Siyang on May 30, 2022	11.5658 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	3.17 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	1643.1 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	232.5 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	174.2 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	177.2 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	138.4 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	434.4 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	394.4 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	310.1 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	862.7 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	392.4 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	1346.2 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	244.7 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	339.2 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	355.1 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	295.7 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	19.2 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Apovincaminic acid	CCC12CCCN3CCC4=C(C13)N(C1=CC=CC=C41)C(=C2)C(O)=O	4404.1	Standard polar	33892256
Apovincaminic acid	CCC12CCCN3CCC4=C(C13)N(C1=CC=CC=C41)C(=C2)C(O)=O	2710.2	Standard non polar	33892256
Apovincaminic acid	CCC12CCCN3CCC4=C(C13)N(C1=CC=CC=C41)C(=C2)C(O)=O	3004.7	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 - Apovincaminic acid GC-MS (Non-derivatized) - 70eV, Positive	splash10-0udl-1091000000-b693a247fd687fce6ead	2021-09-23	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Apovincaminic acid GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Apovincaminic acid GC-MS (TMS_1_1) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Apovincaminic acid GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-11-03	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 - Apovincaminic acid 10V, Positive-QTOF	splash10-00di-0009000000-4311325ab2bb597c4814	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Apovincaminic acid 20V, Positive-QTOF	splash10-00di-0009000000-6b801274e78f91c8aa78	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Apovincaminic acid 40V, Positive-QTOF	splash10-0fkc-0496000000-2a33e1387255710aa510	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Apovincaminic acid 10V, Negative-QTOF	splash10-00di-0009000000-ef145f7b42b2cd0c897b	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Apovincaminic acid 20V, Negative-QTOF	splash10-00di-0019000000-d4edc1a95a8b6b35cc4f	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Apovincaminic acid 40V, Negative-QTOF	splash10-002b-0094000000-83dadb2a106f62b4f842	2021-10-12	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Blood

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	31557052	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

Not Available

KNApSAcK ID

Not Available

Chemspider ID

4367731

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

5196232

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Barupal DK, Fiehn O: Generating the Blood Exposome Database Using a Comprehensive Text Mining and Database Fusion Approach. Environ Health Perspect. 2019 Sep;127(9):97008. doi: 10.1289/EHP4713. Epub 2019 Sep 26. [PubMed:31557052 ]

Showing metabocard for Apovincaminic acid (HMDB0248528)

MOL for HMDB0248528 (Apovincaminic acid)

3D MOL for HMDB0248528 (Apovincaminic acid)

3D SDF for HMDB0248528 (Apovincaminic acid)

3D-SDF for HMDB0248528 (Apovincaminic acid)

PDB for HMDB0248528 (Apovincaminic acid)

3D PDB for HMDB0248528 (Apovincaminic acid)

SMILES for HMDB0248528 (Apovincaminic acid)

INCHI for HMDB0248528 (Apovincaminic acid)

Structure for HMDB0248528 (Apovincaminic acid)

3D Structure for HMDB0248528 (Apovincaminic acid)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra