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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-11 11:25:42 UTC

Update Date

2022-11-23 22:11:27 UTC

HMDB ID

HMDB0253201

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Homocamptothecin

Description

Homocamptothecin, also known as HCPT, belongs to the class of organic compounds known as quinolines and derivatives. Quinolines and derivatives are compounds containing a quinoline moiety, which consists of a benzene ring fused to a pyrimidine ring to form benzo[b]azabenzene. Based on a literature review a significant number of articles have been published on Homocamptothecin. This compound has been identified in human blood as reported by (PMID: 31557052 ). Homocamptothecin is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically Homocamptothecin 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

  Mrv1652309112113262D          

 27 31  0  0  0  0            999 V2000
    2.2358   -1.5189    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1074   -0.7039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3374   -0.4077    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5151   -0.4748    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0500    0.1262    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8367   -0.1222    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0675    0.9428    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7792    1.3601    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5492    1.0638    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7976    0.2771    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6031    0.0989    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1602    0.7073    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9852    0.7005    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5321    0.0828    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.3405    0.2477    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8874   -0.3700    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6958   -0.2052    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9572    0.5773    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4103    1.1950    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6019    1.0302    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0550    1.6478    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2466    1.4830    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5832    1.9734    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9118    1.4941    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.1063    1.6723    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8578    2.4590    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2199   -1.2242    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  2  0  0  0  0
  5  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
  3 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 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
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 15 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  2  0  0  0  0
 13 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 12 24  1  0  0  0  0
 24 25  1  0  0  0  0
  9 25  1  0  0  0  0
 25 26  2  0  0  0  0
  3 27  1  0  0  0  0
M  END

HMDB0253201
     RDKit          3D
homocamptothecin
 45 49  0  0  0  0  0  0  0  0999 V2000
   -4.8992    1.7553   -0.6999 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7750    0.7655   -0.9426 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9007    0.7274    0.2749 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3695    1.9921    0.5165 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6270    0.3027    1.5208 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4998   -0.8324    1.2075 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7207   -0.6352    1.3979 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0726   -2.0632    0.7319 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0757   -2.4526   -0.1613 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8460   -1.6307   -0.1187 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7942   -0.2602    0.0699 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5624    0.3642    0.0838 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5532   -0.4260   -0.0932 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4775   -1.7765   -0.2775 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7159   -2.3919   -0.2925 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8317   -3.6231   -0.4578 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7832   -2.3499   -0.4356 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6932   -1.1624   -0.3238 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0817   -1.1069   -0.3989 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6805    0.1220   -0.2627 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0704    0.1977   -0.3351 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7318    1.3989   -0.2066 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9903    2.5267   -0.0046 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5978    2.4770    0.0715 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9390    1.2728   -0.0576 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6014    1.1537    0.0056 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.9712   -0.0155   -0.1203 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5651    2.7389   -1.0844 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8436    1.4340   -1.1671 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0684    1.8372    0.3858 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1379    1.1017   -1.7909 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2189   -0.2012   -1.1758 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3900    2.5794   -0.2729 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1298    1.1244    2.0503 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8364   -0.0723    2.2315 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5212   -2.4947   -1.1839 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8204   -3.5174    0.0801 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4859    1.4413    0.2299 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0205   -3.1116    0.3357 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8939   -2.7238   -1.4640 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6843   -1.9939   -0.5589 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6126   -0.7225   -0.4961 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.8202    1.3828   -0.2738 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4895    3.4831    0.0993 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0157    3.3855    0.2333 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
  3  5  1  0
  5  6  1  0
  6  7  2  0
  6  8  1  0
  8  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  1  0
 15 16  2  0
 14 17  1  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  2  0
 23 24  1  0
 24 25  2  0
 25 26  1  0
 26 27  2  0
 11  3  1  0
 27 13  1  0
 15 10  1  0
 27 18  1  0
 25 20  1  0
  1 28  1  0
  1 29  1  0
  1 30  1  0
  2 31  1  0
  2 32  1  0
  4 33  1  0
  5 34  1  0
  5 35  1  0
  9 36  1  0
  9 37  1  0
 12 38  1  0
 17 39  1  0
 17 40  1  0
 19 41  1  0
 21 42  1  0
 22 43  1  0
 23 44  1  0
 24 45  1  0
M  END

  Mrv1652309112113262D          

 27 31  0  0  0  0            999 V2000
    2.2358   -1.5189    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1074   -0.7039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3374   -0.4077    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5151   -0.4748    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0500    0.1262    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8367   -0.1222    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0675    0.9428    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7792    1.3601    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5492    1.0638    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7976    0.2771    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6031    0.0989    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1602    0.7073    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9852    0.7005    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5321    0.0828    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.3405    0.2477    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8874   -0.3700    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6958   -0.2052    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9572    0.5773    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4103    1.1950    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6019    1.0302    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0550    1.6478    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2466    1.4830    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5832    1.9734    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9118    1.4941    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.1063    1.6723    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8578    2.4590    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2199   -1.2242    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  2  0  0  0  0
  5  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
  3 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 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
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 15 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  2  0  0  0  0
 13 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 12 24  1  0  0  0  0
 24 25  1  0  0  0  0
  9 25  1  0  0  0  0
 25 26  2  0  0  0  0
  3 27  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0253201

> <DATABASE_NAME>
hmdb

> <SMILES>
CCC1(O)CC(=O)OCC2=C1C=C1N(CC3=CC4=CC=CC=C4N=C13)C2=O

> <INCHI_IDENTIFIER>
InChI=1S/C21H18N2O4/c1-2-21(26)9-18(24)27-11-14-15(21)8-17-19-13(10-23(17)20(14)25)7-12-5-3-4-6-16(12)22-19/h3-8,26H,2,9-11H2,1H3

> <INCHI_KEY>
PAEZRCINULFAGO-UHFFFAOYSA-N

> <FORMULA>
C21H18N2O4

> <MOLECULAR_WEIGHT>
362.385

> <EXACT_MASS>
362.126657068

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
45

> <JCHEM_AVERAGE_POLARIZABILITY>
38.655545572694024

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
20-ethyl-20-hydroxy-17-oxa-3,13-diazapentacyclo[11.9.0.0^{2,11}.0^{4,9}.0^{15,21}]docosa-1(22),2,4,6,8,10,15(21)-heptaene-14,18-dione

> <ALOGPS_LOGP>
1.91

> <JCHEM_LOGP>
1.152877539

> <ALOGPS_LOGS>
-3.05

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.80876268321446

> <JCHEM_PKA_STRONGEST_BASIC>
3.0760440281649215

> <JCHEM_POLAR_SURFACE_AREA>
79.73

> <JCHEM_REFRACTIVITY>
99.04169999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.21e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
20-ethyl-20-hydroxy-17-oxa-3,13-diazapentacyclo[11.9.0.0^{2,11}.0^{4,9}.0^{15,21}]docosa-1(22),2,4,6,8,10,15(21)-heptaene-14,18-dione

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0253201
     RDKit          3D
homocamptothecin
 45 49  0  0  0  0  0  0  0  0999 V2000
   -4.8992    1.7553   -0.6999 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7750    0.7655   -0.9426 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9007    0.7274    0.2749 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3695    1.9921    0.5165 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6270    0.3027    1.5208 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4998   -0.8324    1.2075 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7207   -0.6352    1.3979 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0726   -2.0632    0.7319 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0757   -2.4526   -0.1613 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8460   -1.6307   -0.1187 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7942   -0.2602    0.0699 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5624    0.3642    0.0838 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5532   -0.4260   -0.0932 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4775   -1.7765   -0.2775 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7159   -2.3919   -0.2925 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8317   -3.6231   -0.4578 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7832   -2.3499   -0.4356 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6932   -1.1624   -0.3238 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0817   -1.1069   -0.3989 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6805    0.1220   -0.2627 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0704    0.1977   -0.3351 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7318    1.3989   -0.2066 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9903    2.5267   -0.0046 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5978    2.4770    0.0715 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9390    1.2728   -0.0576 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6014    1.1537    0.0056 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.9712   -0.0155   -0.1203 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5651    2.7389   -1.0844 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8436    1.4340   -1.1671 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0684    1.8372    0.3858 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1379    1.1017   -1.7909 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2189   -0.2012   -1.1758 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3900    2.5794   -0.2729 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1298    1.1244    2.0503 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8364   -0.0723    2.2315 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5212   -2.4947   -1.1839 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8204   -3.5174    0.0801 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4859    1.4413    0.2299 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0205   -3.1116    0.3357 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8939   -2.7238   -1.4640 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6843   -1.9939   -0.5589 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6126   -0.7225   -0.4961 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.8202    1.3828   -0.2738 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4895    3.4831    0.0993 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0157    3.3855    0.2333 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
  3  5  1  0
  5  6  1  0
  6  7  2  0
  6  8  1  0
  8  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  1  0
 15 16  2  0
 14 17  1  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  2  0
 23 24  1  0
 24 25  2  0
 25 26  1  0
 26 27  2  0
 11  3  1  0
 27 13  1  0
 15 10  1  0
 27 18  1  0
 25 20  1  0
  1 28  1  0
  1 29  1  0
  1 30  1  0
  2 31  1  0
  2 32  1  0
  4 33  1  0
  5 34  1  0
  5 35  1  0
  9 36  1  0
  9 37  1  0
 12 38  1  0
 17 39  1  0
 17 40  1  0
 19 41  1  0
 21 42  1  0
 22 43  1  0
 23 44  1  0
 24 45  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       4.173  -2.835   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       3.934  -1.314   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.496  -0.761   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.962  -0.886   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -0.093   0.236   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0      -1.562  -0.228   0.000  0.00  0.00           O+0
HETATM    7  O   UNK     0       0.126   1.760   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       1.455   2.539   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.892   1.986   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       3.355   0.517   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.859   0.185   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       5.899   1.320   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       7.439   1.308   0.000  0.00  0.00           C+0
HETATM   14  N   UNK     0       8.460   0.155   0.000  0.00  0.00           N+0
HETATM   15  C   UNK     0       9.969   0.462   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      10.990  -0.691   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      12.499  -0.383   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      12.987   1.078   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      11.966   2.231   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      10.457   1.923   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       9.436   3.076   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       7.927   2.768   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       6.689   3.684   0.000  0.00  0.00           C+0
HETATM   24  N   UNK     0       5.435   2.789   0.000  0.00  0.00           N+0
HETATM   25  C   UNK     0       3.932   3.122   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0       3.468   4.590   0.000  0.00  0.00           O+0
HETATM   27  O   UNK     0       2.277  -2.285   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   10   27                                             
CONECT    4    3    5                                                       
CONECT    5    4    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   25                                                  
CONECT   10    9    3   11                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13   24                                                  
CONECT   13   12   14   22                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16   20                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   15   21                                                  
CONECT   21   20   22                                                       
CONECT   22   21   13   23                                                  
CONECT   23   22   24                                                       
CONECT   24   23   12   25                                                  
CONECT   25   24    9   26                                                  
CONECT   26   25                                                            
CONECT   27    3                                                            
MASTER        0    0    0    0    0    0    0    0   27    0   62    0
END

COMPND    HMDB0253201
HETATM    1  C1  UNL     1      -4.899   1.755  -0.700  1.00  0.00           C  
HETATM    2  C2  UNL     1      -3.775   0.765  -0.943  1.00  0.00           C  
HETATM    3  C3  UNL     1      -2.901   0.727   0.275  1.00  0.00           C  
HETATM    4  O1  UNL     1      -2.369   1.992   0.516  1.00  0.00           O  
HETATM    5  C4  UNL     1      -3.627   0.303   1.521  1.00  0.00           C  
HETATM    6  C5  UNL     1      -4.500  -0.832   1.208  1.00  0.00           C  
HETATM    7  O2  UNL     1      -5.721  -0.635   1.398  1.00  0.00           O  
HETATM    8  O3  UNL     1      -4.073  -2.063   0.732  1.00  0.00           O  
HETATM    9  C6  UNL     1      -3.076  -2.453  -0.161  1.00  0.00           C  
HETATM   10  C7  UNL     1      -1.846  -1.631  -0.119  1.00  0.00           C  
HETATM   11  C8  UNL     1      -1.794  -0.260   0.070  1.00  0.00           C  
HETATM   12  C9  UNL     1      -0.562   0.364   0.084  1.00  0.00           C  
HETATM   13  C10 UNL     1       0.553  -0.426  -0.093  1.00  0.00           C  
HETATM   14  N1  UNL     1       0.477  -1.776  -0.278  1.00  0.00           N  
HETATM   15  C11 UNL     1      -0.716  -2.392  -0.292  1.00  0.00           C  
HETATM   16  O4  UNL     1      -0.832  -3.623  -0.458  1.00  0.00           O  
HETATM   17  C12 UNL     1       1.783  -2.350  -0.436  1.00  0.00           C  
HETATM   18  C13 UNL     1       2.693  -1.162  -0.324  1.00  0.00           C  
HETATM   19  C14 UNL     1       4.082  -1.107  -0.399  1.00  0.00           C  
HETATM   20  C15 UNL     1       4.681   0.122  -0.263  1.00  0.00           C  
HETATM   21  C16 UNL     1       6.070   0.198  -0.335  1.00  0.00           C  
HETATM   22  C17 UNL     1       6.732   1.399  -0.207  1.00  0.00           C  
HETATM   23  C18 UNL     1       5.990   2.527  -0.005  1.00  0.00           C  
HETATM   24  C19 UNL     1       4.598   2.477   0.072  1.00  0.00           C  
HETATM   25  C20 UNL     1       3.939   1.273  -0.058  1.00  0.00           C  
HETATM   26  N2  UNL     1       2.601   1.154   0.006  1.00  0.00           N  
HETATM   27  C21 UNL     1       1.971  -0.016  -0.120  1.00  0.00           C  
HETATM   28  H1  UNL     1      -4.565   2.739  -1.084  1.00  0.00           H  
HETATM   29  H2  UNL     1      -5.844   1.434  -1.167  1.00  0.00           H  
HETATM   30  H3  UNL     1      -5.068   1.837   0.386  1.00  0.00           H  
HETATM   31  H4  UNL     1      -3.138   1.102  -1.791  1.00  0.00           H  
HETATM   32  H5  UNL     1      -4.219  -0.201  -1.176  1.00  0.00           H  
HETATM   33  H6  UNL     1      -2.390   2.579  -0.273  1.00  0.00           H  
HETATM   34  H7  UNL     1      -4.130   1.124   2.050  1.00  0.00           H  
HETATM   35  H8  UNL     1      -2.836  -0.072   2.231  1.00  0.00           H  
HETATM   36  H9  UNL     1      -3.521  -2.495  -1.184  1.00  0.00           H  
HETATM   37  H10 UNL     1      -2.820  -3.517   0.080  1.00  0.00           H  
HETATM   38  H11 UNL     1      -0.486   1.441   0.230  1.00  0.00           H  
HETATM   39  H12 UNL     1       2.020  -3.112   0.336  1.00  0.00           H  
HETATM   40  H13 UNL     1       1.894  -2.724  -1.464  1.00  0.00           H  
HETATM   41  H14 UNL     1       4.684  -1.994  -0.559  1.00  0.00           H  
HETATM   42  H15 UNL     1       6.613  -0.722  -0.496  1.00  0.00           H  
HETATM   43  H16 UNL     1       7.820   1.383  -0.274  1.00  0.00           H  
HETATM   44  H17 UNL     1       6.490   3.483   0.099  1.00  0.00           H  
HETATM   45  H18 UNL     1       4.016   3.386   0.233  1.00  0.00           H  
CONECT    1    2   28   29   30
CONECT    2    3   31   32
CONECT    3    4    5   11
CONECT    4   33
CONECT    5    6   34   35
CONECT    6    7    7    8
CONECT    8    9
CONECT    9   10   36   37
CONECT   10   11   11   15
CONECT   11   12
CONECT   12   13   13   38
CONECT   13   14   27
CONECT   14   15   17
CONECT   15   16   16
CONECT   17   18   39   40
CONECT   18   19   19   27
CONECT   19   20   41
CONECT   20   21   21   25
CONECT   21   22   42
CONECT   22   23   23   43
CONECT   23   24   44
CONECT   24   25   25   45
CONECT   25   26
CONECT   26   27   27
END

HMDB0253201
     RDKit          3D
homocamptothecin
 45 49  0  0  0  0  0  0  0  0999 V2000
   -4.8992    1.7553   -0.6999 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7750    0.7655   -0.9426 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9007    0.7274    0.2749 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3695    1.9921    0.5165 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6270    0.3027    1.5208 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4998   -0.8324    1.2075 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7207   -0.6352    1.3979 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0726   -2.0632    0.7319 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0757   -2.4526   -0.1613 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8460   -1.6307   -0.1187 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7942   -0.2602    0.0699 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5624    0.3642    0.0838 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5532   -0.4260   -0.0932 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4775   -1.7765   -0.2775 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7159   -2.3919   -0.2925 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8317   -3.6231   -0.4578 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7832   -2.3499   -0.4356 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6932   -1.1624   -0.3238 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0817   -1.1069   -0.3989 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6805    0.1220   -0.2627 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0704    0.1977   -0.3351 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7318    1.3989   -0.2066 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9903    2.5267   -0.0046 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5978    2.4770    0.0715 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9390    1.2728   -0.0576 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6014    1.1537    0.0056 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.9712   -0.0155   -0.1203 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5651    2.7389   -1.0844 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8436    1.4340   -1.1671 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0684    1.8372    0.3858 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1379    1.1017   -1.7909 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2189   -0.2012   -1.1758 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3900    2.5794   -0.2729 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1298    1.1244    2.0503 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8364   -0.0723    2.2315 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5212   -2.4947   -1.1839 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8204   -3.5174    0.0801 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4859    1.4413    0.2299 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0205   -3.1116    0.3357 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8939   -2.7238   -1.4640 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6843   -1.9939   -0.5589 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6126   -0.7225   -0.4961 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.8202    1.3828   -0.2738 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4895    3.4831    0.0993 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0157    3.3855    0.2333 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
  3  5  1  0
  5  6  1  0
  6  7  2  0
  6  8  1  0
  8  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  1  0
 15 16  2  0
 14 17  1  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  2  0
 23 24  1  0
 24 25  2  0
 25 26  1  0
 26 27  2  0
 11  3  1  0
 27 13  1  0
 15 10  1  0
 27 18  1  0
 25 20  1  0
  1 28  1  0
  1 29  1  0
  1 30  1  0
  2 31  1  0
  2 32  1  0
  4 33  1  0
  5 34  1  0
  5 35  1  0
  9 36  1  0
  9 37  1  0
 12 38  1  0
 17 39  1  0
 17 40  1  0
 19 41  1  0
 21 42  1  0
 22 43  1  0
 23 44  1  0
 24 45  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
HCPT	MeSH

Chemical Formula

C₂₁H₁₈N₂O₄

Average Molecular Weight

362.385

Monoisotopic Molecular Weight

362.126657068

IUPAC Name

20-ethyl-20-hydroxy-17-oxa-3,13-diazapentacyclo[11.9.0.0^{2,11}.0^{4,9}.0^{15,21}]docosa-1(22),2,4,6,8,10,15(21)-heptaene-14,18-dione

Traditional Name

20-ethyl-20-hydroxy-17-oxa-3,13-diazapentacyclo[11.9.0.0^{2,11}.0^{4,9}.0^{15,21}]docosa-1(22),2,4,6,8,10,15(21)-heptaene-14,18-dione

CAS Registry Number

Not Available

SMILES

CCC1(O)CC(=O)OCC2=C1C=C1N(CC3=CC4=CC=CC=C4N=C13)C2=O

InChI Identifier

InChI=1S/C21H18N2O4/c1-2-21(26)9-18(24)27-11-14-15(21)8-17-19-13(10-23(17)20(14)25)7-12-5-3-4-6-16(12)22-19/h3-8,26H,2,9-11H2,1H3

InChI Key

PAEZRCINULFAGO-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as quinolines and derivatives. Quinolines and derivatives are compounds containing a quinoline moiety, which consists of a benzene ring fused to a pyrimidine ring to form benzo[b]azabenzene.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Quinolines and derivatives

Sub Class

Not Available

Direct Parent

Quinolines and derivatives

Alternative Parents

Substituents

Quinoline
Pyridinone
Pyridine
Benzenoid
Tertiary alcohol
Heteroaromatic compound
Carboxylic acid ester
Lactam
Lactone
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Oxacycle
Azacycle
Organic oxide
Organic oxygen compound
Organic nitrogen compound
Organooxygen compound
Organonitrogen compound
Carbonyl group
Alcohol
Hydrocarbon derivative
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	1.91	ALOGPS
logP	1.15	ChemAxon
logS	-3	ALOGPS
pKa (Strongest Acidic)	13.81	ChemAxon
pKa (Strongest Basic)	3.08	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	79.73 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	99.04 m³·mol⁻¹	ChemAxon
Polarizability	38.66 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]-	220.113	30932474
DeepCCS	[M+Na]+	195.341	30932474

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
homocamptothecin	CCC1(O)CC(=O)OCC2=C1C=C1N(CC3=CC4=CC=CC=C4N=C13)C2=O	4468.1	Standard polar	33892256
homocamptothecin	CCC1(O)CC(=O)OCC2=C1C=C1N(CC3=CC4=CC=CC=C4N=C13)C2=O	3149.9	Standard non polar	33892256
homocamptothecin	CCC1(O)CC(=O)OCC2=C1C=C1N(CC3=CC4=CC=CC=C4N=C13)C2=O	3798.8	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 - Homocamptothecin GC-MS (Non-derivatized) - 70eV, Positive	splash10-0ikc-1095000000-0452e7539f632e822a00	2021-09-24	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Homocamptothecin GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Homocamptothecin GC-MS (TMS_1_1) - 70eV, Positive	Not Available	2021-11-04	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Homocamptothecin GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-11-04	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 - Homocamptothecin 10V, Positive-QTOF	splash10-03dj-0009000000-f6233da986197d9819f0	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Homocamptothecin 20V, Positive-QTOF	splash10-03dj-0009000000-baf26f521778c1e59f52	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Homocamptothecin 40V, Positive-QTOF	splash10-0002-2179000000-cd99f1b9f65741b88203	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Homocamptothecin 10V, Negative-QTOF	splash10-03di-0009000000-384937f73093dab526a6	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Homocamptothecin 20V, Negative-QTOF	splash10-03xr-0019000000-5b85247aac0c8c5bb3d6	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Homocamptothecin 40V, Negative-QTOF	splash10-00kb-3369000000-26156ce187fb4eede728	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

8039473

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

9863779

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 Homocamptothecin (HMDB0253201)

MOL for HMDB0253201 (Homocamptothecin)

3D MOL for HMDB0253201 (Homocamptothecin)

3D SDF for HMDB0253201 (Homocamptothecin)

3D-SDF for HMDB0253201 (Homocamptothecin)

PDB for HMDB0253201 (Homocamptothecin)

3D PDB for HMDB0253201 (Homocamptothecin)

SMILES for HMDB0253201 (Homocamptothecin)

INCHI for HMDB0253201 (Homocamptothecin)

Structure for HMDB0253201 (Homocamptothecin)

3D Structure for HMDB0253201 (Homocamptothecin)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra