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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-11 08:06:51 UTC

Update Date

2021-09-26 23:02:42 UTC

HMDB ID

HMDB0250956

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Dehydromonocrotaline

Description

Dehydromonocrotaline belongs to the class of organic compounds known as pyrrolizines. Pyrrolizines are compounds containing a pyrrolizine moiety, which consists of a pyrrole ring fused to a pyrrolidine ring. Based on a literature review a significant number of articles have been published on Dehydromonocrotaline. This compound has been identified in human blood as reported by (PMID: 31557052 ). Dehydromonocrotaline is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically Dehydromonocrotaline 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

HMDB0250956
     RDKit          3D
Dehydromonocrotaline
 44 46  0  0  0  0  0  0  0  0999 V2000
   -2.1269    2.6454   -1.0729 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3219    1.4567   -0.5856 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1420    1.9207    0.2505 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5163    2.9008    0.9794 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0237    1.3119    0.1339 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1618    0.8284    0.6353 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3519    1.6672    0.0984 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5444    0.7299    0.2361 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9518   -0.5990    0.0400 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.1423   -1.8939   -0.2685 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9318   -2.5944   -0.2477 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9759   -1.6672    0.0900 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6693   -0.4874    0.2484 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5494   -1.5008    0.3088 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3654   -2.5026    0.2756 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7014   -2.1158    0.0975 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5586   -2.9008    0.6490 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1755   -0.9334   -0.6404 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6169   -1.2675   -1.1277 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5320   -0.7838   -1.8969 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1570    0.3875    0.0774 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9828    0.3094    1.5519 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4892    0.8917   -0.0664 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1145    2.2298   -1.3991 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2882    3.3110   -0.1831 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6056    3.1617   -1.8788 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9363    0.9926   -1.5287 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3147    0.8938    1.7480 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4596    2.6023    0.6379 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1755    1.7924   -0.9876 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9880    0.7566    1.2290 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2739    0.8582   -0.5865 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1024   -2.3558   -0.5060 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6989   -3.6129   -0.4355 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4988   -1.0736    1.3461 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2609   -0.7883   -0.4958 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0484   -0.3660   -1.6317 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5139   -2.0761   -1.8776 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2347   -1.6030   -0.2936 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6826   -1.6506   -2.3653 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1032   -0.7715    1.8455 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7627    0.8655    2.0702 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9941    0.6990    1.9010 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1050    0.3321    0.5039 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
  3  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 12 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  2  0
 16 18  1  0
 18 19  1  0
 18 20  1  0
 18 21  1  0
 21 22  1  0
 21 23  1  0
 21  2  1  0
 13  6  1  0
 13  9  1  0
  1 24  1  0
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  1 26  1  0
  2 27  1  0
  6 28  1  0
  7 29  1  0
  7 30  1  0
  8 31  1  0
  8 32  1  0
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 19 37  1  0
 19 38  1  0
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 20 40  1  0
 22 41  1  0
 22 42  1  0
 22 43  1  0
 23 44  1  0
M  END

  Mrv1652309112110072D          

 23 25  0  0  0  0            999 V2000
    4.7720   -3.3727    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1330   -2.8508    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3616   -3.1433    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2291   -3.9576    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7226   -2.6214    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9512   -2.9139    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4990   -3.6039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7030   -3.3871    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6632   -2.5630    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.3122   -2.3920    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4446   -1.5777    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2741   -1.2214    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6517   -0.4878    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4660   -0.6203    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0518   -0.0394    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5917   -1.4357    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2654   -2.0365    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8257   -1.4310    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0820   -2.1541    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1760   -0.8532    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3982   -1.2624    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5989   -1.2297    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1467   -1.9197    0.0000 C   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  2  0  0  0  0
  3  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
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  6 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 14 16  1  0  0  0  0
 16 17  1  0  0  0  0
  2 17  1  0  0  0  0
 17 18  1  0  0  0  0
 17 19  1  0  0  0  0
 16 20  1  0  0  0  0
 16 21  1  0  0  0  0
 11 22  1  0  0  0  0
 22 23  2  0  0  0  0
  9 23  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0250956

> <DATABASE_NAME>
hmdb

> <SMILES>
CC1C(=O)OC2CCN3C=CC(COC(=O)C(C)(O)C1(C)O)=C23

> <INCHI_IDENTIFIER>
InChI=1S/C16H21NO6/c1-9-13(18)23-11-5-7-17-6-4-10(12(11)17)8-22-14(19)16(3,21)15(9,2)20/h4,6,9,11,20-21H,5,7-8H2,1-3H3

> <INCHI_KEY>
ZONSVLURFASOJK-UHFFFAOYSA-N

> <FORMULA>
C16H21NO6

> <MOLECULAR_WEIGHT>
323.345

> <EXACT_MASS>
323.1368874

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
44

> <JCHEM_AVERAGE_POLARIZABILITY>
31.700063411964482

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
5,6-dihydroxy-4,5,6-trimethyl-2,8-dioxa-13-azatricyclo[8.5.1.0^{13,16}]hexadeca-10(16),11-diene-3,7-dione

> <ALOGPS_LOGP>
0.99

> <JCHEM_LOGP>
0.4516041610000011

> <ALOGPS_LOGS>
-1.96

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.94107008117474

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.494031084909846

> <JCHEM_PKA_STRONGEST_BASIC>
-3.5955546660310214

> <JCHEM_POLAR_SURFACE_AREA>
97.99000000000001

> <JCHEM_REFRACTIVITY>
79.5687

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.53e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
5,6-dihydroxy-4,5,6-trimethyl-2,8-dioxa-13-azatricyclo[8.5.1.0^{13,16}]hexadeca-10(16),11-diene-3,7-dione

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0250956
     RDKit          3D
Dehydromonocrotaline
 44 46  0  0  0  0  0  0  0  0999 V2000
   -2.1269    2.6454   -1.0729 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3219    1.4567   -0.5856 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1420    1.9207    0.2505 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5163    2.9008    0.9794 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0237    1.3119    0.1339 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1618    0.8284    0.6353 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3519    1.6672    0.0984 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5444    0.7299    0.2361 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9518   -0.5990    0.0400 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.1423   -1.8939   -0.2685 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9318   -2.5944   -0.2477 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9759   -1.6672    0.0900 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6693   -0.4874    0.2484 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5494   -1.5008    0.3088 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3654   -2.5026    0.2756 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7014   -2.1158    0.0975 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5586   -2.9008    0.6490 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1755   -0.9334   -0.6404 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6169   -1.2675   -1.1277 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5320   -0.7838   -1.8969 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1570    0.3875    0.0774 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9828    0.3094    1.5519 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4892    0.8917   -0.0664 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1145    2.2298   -1.3991 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2882    3.3110   -0.1831 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6056    3.1617   -1.8788 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9363    0.9926   -1.5287 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3147    0.8938    1.7480 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4596    2.6023    0.6379 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1755    1.7924   -0.9876 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9880    0.7566    1.2290 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2739    0.8582   -0.5865 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1024   -2.3558   -0.5060 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6989   -3.6129   -0.4355 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4988   -1.0736    1.3461 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2609   -0.7883   -0.4958 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0484   -0.3660   -1.6317 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5139   -2.0761   -1.8776 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2347   -1.6030   -0.2936 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6826   -1.6506   -2.3653 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1032   -0.7715    1.8455 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7627    0.8655    2.0702 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9941    0.6990    1.9010 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1050    0.3321    0.5039 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
  3  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 12 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  2  0
 16 18  1  0
 18 19  1  0
 18 20  1  0
 18 21  1  0
 21 22  1  0
 21 23  1  0
 21  2  1  0
 13  6  1  0
 13  9  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  2 27  1  0
  6 28  1  0
  7 29  1  0
  7 30  1  0
  8 31  1  0
  8 32  1  0
 10 33  1  0
 11 34  1  0
 14 35  1  0
 14 36  1  0
 19 37  1  0
 19 38  1  0
 19 39  1  0
 20 40  1  0
 22 41  1  0
 22 42  1  0
 22 43  1  0
 23 44  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       8.908  -6.296   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       7.715  -5.322   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       6.275  -5.867   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       6.028  -7.388   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0       5.082  -4.893   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       3.642  -5.439   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.798  -6.727   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.312  -6.323   0.000  0.00  0.00           C+0
HETATM    9  N   UNK     0       1.238  -4.784   0.000  0.00  0.00           N+0
HETATM   10  C   UNK     0       2.449  -4.465   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.697  -2.945   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.245  -2.280   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       4.950  -0.911   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       6.470  -1.158   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       7.563  -0.073   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       6.704  -2.680   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       7.962  -3.802   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       9.008  -2.671   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       9.486  -4.021   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       7.795  -1.593   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       8.210  -2.356   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       1.118  -2.295   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       0.274  -3.584   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   17                                                  
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6                                                       
CONECT    6    5    7   10                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   23                                                  
CONECT   10    9    6   11                                                  
CONECT   11   10   12   22                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14   17   20   21                                             
CONECT   17   16    2   18   19                                             
CONECT   18   17                                                            
CONECT   19   17                                                            
CONECT   20   16                                                            
CONECT   21   16                                                            
CONECT   22   11   23                                                       
CONECT   23   22    9                                                       
MASTER        0    0    0    0    0    0    0    0   23    0   50    0
END

COMPND    HMDB0250956
HETATM    1  C1  UNL     1      -2.127   2.645  -1.073  1.00  0.00           C  
HETATM    2  C2  UNL     1      -1.322   1.457  -0.586  1.00  0.00           C  
HETATM    3  C3  UNL     1      -0.142   1.921   0.251  1.00  0.00           C  
HETATM    4  O1  UNL     1      -0.516   2.901   0.979  1.00  0.00           O  
HETATM    5  O2  UNL     1       1.024   1.312   0.134  1.00  0.00           O  
HETATM    6  C4  UNL     1       2.162   0.828   0.635  1.00  0.00           C  
HETATM    7  C5  UNL     1       3.352   1.667   0.098  1.00  0.00           C  
HETATM    8  C6  UNL     1       4.544   0.730   0.236  1.00  0.00           C  
HETATM    9  N1  UNL     1       3.952  -0.599   0.040  1.00  0.00           N  
HETATM   10  C7  UNL     1       4.142  -1.894  -0.268  1.00  0.00           C  
HETATM   11  C8  UNL     1       2.932  -2.594  -0.248  1.00  0.00           C  
HETATM   12  C9  UNL     1       1.976  -1.667   0.090  1.00  0.00           C  
HETATM   13  C10 UNL     1       2.669  -0.487   0.248  1.00  0.00           C  
HETATM   14  C11 UNL     1       0.549  -1.501   0.309  1.00  0.00           C  
HETATM   15  O3  UNL     1      -0.365  -2.503   0.276  1.00  0.00           O  
HETATM   16  C12 UNL     1      -1.701  -2.116   0.098  1.00  0.00           C  
HETATM   17  O4  UNL     1      -2.559  -2.901   0.649  1.00  0.00           O  
HETATM   18  C13 UNL     1      -2.176  -0.933  -0.640  1.00  0.00           C  
HETATM   19  C14 UNL     1      -3.617  -1.268  -1.128  1.00  0.00           C  
HETATM   20  O5  UNL     1      -1.532  -0.784  -1.897  1.00  0.00           O  
HETATM   21  C15 UNL     1      -2.157   0.387   0.077  1.00  0.00           C  
HETATM   22  C16 UNL     1      -1.983   0.309   1.552  1.00  0.00           C  
HETATM   23  O6  UNL     1      -3.489   0.892  -0.066  1.00  0.00           O  
HETATM   24  H1  UNL     1      -3.115   2.230  -1.399  1.00  0.00           H  
HETATM   25  H2  UNL     1      -2.288   3.311  -0.183  1.00  0.00           H  
HETATM   26  H3  UNL     1      -1.606   3.162  -1.879  1.00  0.00           H  
HETATM   27  H4  UNL     1      -0.936   0.993  -1.529  1.00  0.00           H  
HETATM   28  H5  UNL     1       2.315   0.894   1.748  1.00  0.00           H  
HETATM   29  H6  UNL     1       3.460   2.602   0.638  1.00  0.00           H  
HETATM   30  H7  UNL     1       3.176   1.792  -0.988  1.00  0.00           H  
HETATM   31  H8  UNL     1       4.988   0.757   1.229  1.00  0.00           H  
HETATM   32  H9  UNL     1       5.274   0.858  -0.586  1.00  0.00           H  
HETATM   33  H10 UNL     1       5.102  -2.356  -0.506  1.00  0.00           H  
HETATM   34  H11 UNL     1       2.699  -3.613  -0.436  1.00  0.00           H  
HETATM   35  H12 UNL     1       0.499  -1.074   1.346  1.00  0.00           H  
HETATM   36  H13 UNL     1       0.261  -0.788  -0.496  1.00  0.00           H  
HETATM   37  H14 UNL     1      -4.048  -0.366  -1.632  1.00  0.00           H  
HETATM   38  H15 UNL     1      -3.514  -2.076  -1.878  1.00  0.00           H  
HETATM   39  H16 UNL     1      -4.235  -1.603  -0.294  1.00  0.00           H  
HETATM   40  H17 UNL     1      -1.683  -1.651  -2.365  1.00  0.00           H  
HETATM   41  H18 UNL     1      -2.103  -0.772   1.846  1.00  0.00           H  
HETATM   42  H19 UNL     1      -2.763   0.865   2.070  1.00  0.00           H  
HETATM   43  H20 UNL     1      -0.994   0.699   1.901  1.00  0.00           H  
HETATM   44  H21 UNL     1      -4.105   0.332   0.504  1.00  0.00           H  
CONECT    1    2   24   25   26
CONECT    2    3   21   27
CONECT    3    4    4    5
CONECT    5    6
CONECT    6    7   13   28
CONECT    7    8   29   30
CONECT    8    9   31   32
CONECT    9   10   13
CONECT   10   11   11   33
CONECT   11   12   34
CONECT   12   13   13   14
CONECT   14   15   35   36
CONECT   15   16
CONECT   16   17   17   18
CONECT   18   19   20   21
CONECT   19   37   38   39
CONECT   20   40
CONECT   21   22   23
CONECT   22   41   42   43
CONECT   23   44
END

HMDB0250956
     RDKit          3D
Dehydromonocrotaline
 44 46  0  0  0  0  0  0  0  0999 V2000
   -2.1269    2.6454   -1.0729 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3219    1.4567   -0.5856 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1420    1.9207    0.2505 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5163    2.9008    0.9794 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0237    1.3119    0.1339 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1618    0.8284    0.6353 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3519    1.6672    0.0984 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5444    0.7299    0.2361 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9518   -0.5990    0.0400 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.1423   -1.8939   -0.2685 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9318   -2.5944   -0.2477 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9759   -1.6672    0.0900 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6693   -0.4874    0.2484 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5494   -1.5008    0.3088 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3654   -2.5026    0.2756 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7014   -2.1158    0.0975 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5586   -2.9008    0.6490 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1755   -0.9334   -0.6404 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6169   -1.2675   -1.1277 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5320   -0.7838   -1.8969 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1570    0.3875    0.0774 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9828    0.3094    1.5519 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4892    0.8917   -0.0664 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1145    2.2298   -1.3991 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2882    3.3110   -0.1831 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6056    3.1617   -1.8788 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9363    0.9926   -1.5287 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3147    0.8938    1.7480 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4596    2.6023    0.6379 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1755    1.7924   -0.9876 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9880    0.7566    1.2290 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2739    0.8582   -0.5865 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1024   -2.3558   -0.5060 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6989   -3.6129   -0.4355 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4988   -1.0736    1.3461 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2609   -0.7883   -0.4958 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0484   -0.3660   -1.6317 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5139   -2.0761   -1.8776 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2347   -1.6030   -0.2936 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6826   -1.6506   -2.3653 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1032   -0.7715    1.8455 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7627    0.8655    2.0702 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9941    0.6990    1.9010 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1050    0.3321    0.5039 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
  3  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 12 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  2  0
 16 18  1  0
 18 19  1  0
 18 20  1  0
 18 21  1  0
 21 22  1  0
 21 23  1  0
 21  2  1  0
 13  6  1  0
 13  9  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  2 27  1  0
  6 28  1  0
  7 29  1  0
  7 30  1  0
  8 31  1  0
  8 32  1  0
 10 33  1  0
 11 34  1  0
 14 35  1  0
 14 36  1  0
 19 37  1  0
 19 38  1  0
 19 39  1  0
 20 40  1  0
 22 41  1  0
 22 42  1  0
 22 43  1  0
 23 44  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Not Available

Chemical Formula

C₁₆H₂₁NO₆

Average Molecular Weight

323.345

Monoisotopic Molecular Weight

323.1368874

IUPAC Name

5,6-dihydroxy-4,5,6-trimethyl-2,8-dioxa-13-azatricyclo[8.5.1.0^{13,16}]hexadeca-10(16),11-diene-3,7-dione

Traditional Name

5,6-dihydroxy-4,5,6-trimethyl-2,8-dioxa-13-azatricyclo[8.5.1.0^{13,16}]hexadeca-10(16),11-diene-3,7-dione

CAS Registry Number

Not Available

SMILES

CC1C(=O)OC2CCN3C=CC(COC(=O)C(C)(O)C1(C)O)=C23

InChI Identifier

InChI=1S/C16H21NO6/c1-9-13(18)23-11-5-7-17-6-4-10(12(11)17)8-22-14(19)16(3,21)15(9,2)20/h4,6,9,11,20-21H,5,7-8H2,1-3H3

InChI Key

ZONSVLURFASOJK-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as pyrrolizines. Pyrrolizines are compounds containing a pyrrolizine moiety, which consists of a pyrrole ring fused to a pyrrolidine ring.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Pyrrolizines

Sub Class

Not Available

Direct Parent

Pyrrolizines

Alternative Parents

Substituents

Pyrrolizine
Dicarboxylic acid or derivatives
Pyrrole
Tertiary alcohol
Heteroaromatic compound
1,2-diol
Lactone
Carboxylic acid ester
Oxacycle
Azacycle
Carboxylic acid derivative
Alcohol
Organic oxygen compound
Organooxygen compound
Organonitrogen compound
Organic nitrogen compound
Carbonyl group
Hydrocarbon derivative
Organic oxide
Organopnictogen 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	0.99	ALOGPS
logP	0.45	ChemAxon
logS	-2	ALOGPS
pKa (Strongest Acidic)	11.49	ChemAxon
pKa (Strongest Basic)	-3.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	97.99 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	79.57 m³·mol⁻¹	ChemAxon
Polarizability	31.7 Å³	ChemAxon
Number of Rings	3	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]-	210.653	30932474
DeepCCS	[M+Na]+	186.005	30932474
AllCCS	[M+H]+	173.3	32859911
AllCCS	[M+H-H2O]+	170.2	32859911
AllCCS	[M+NH4]+	176.2	32859911
AllCCS	[M+Na]+	177.0	32859911
AllCCS	[M-H]-	175.6	32859911
AllCCS	[M+Na-2H]-	175.6	32859911
AllCCS	[M+HCOO]-	175.6	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Dehydromonocrotaline	CC1C(=O)OC2CCN3C=CC(COC(=O)C(C)(O)C1(C)O)=C23	3597.0	Standard polar	33892256
Dehydromonocrotaline	CC1C(=O)OC2CCN3C=CC(COC(=O)C(C)(O)C1(C)O)=C23	2275.9	Standard non polar	33892256
Dehydromonocrotaline	CC1C(=O)OC2CCN3C=CC(COC(=O)C(C)(O)C1(C)O)=C23	2638.2	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 - Dehydromonocrotaline GC-MS (Non-derivatized) - 70eV, Positive	splash10-0a4i-0019000000-5cf707c39d5ecfbfeb1b	2021-09-24	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Dehydromonocrotaline GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Dehydromonocrotaline GC-MS (TMS_1_1) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Dehydromonocrotaline GC-MS (TMS_1_2) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Dehydromonocrotaline GC-MS (TMS_2_1) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Dehydromonocrotaline GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Dehydromonocrotaline GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Dehydromonocrotaline GC-MS (TBDMS_2_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 - Dehydromonocrotaline 10V, Positive-QTOF	splash10-00di-0009000000-2aee95e04079b29875d2	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dehydromonocrotaline 20V, Positive-QTOF	splash10-00di-0009000000-6601d022409c6d0efd89	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dehydromonocrotaline 40V, Positive-QTOF	splash10-0592-0079000000-61aeed6cae7aa3302fd6	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dehydromonocrotaline 10V, Negative-QTOF	splash10-00di-0009000000-5f3f1475e5ba743fdd9e	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dehydromonocrotaline 20V, Negative-QTOF	splash10-00di-0009000000-86592619ea6df395f0cc	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dehydromonocrotaline 40V, Negative-QTOF	splash10-052o-0095000000-bb1dcf711cdfceaf83e6	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

501684

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

577090

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 Dehydromonocrotaline (HMDB0250956)

MOL for HMDB0250956 (Dehydromonocrotaline)

3D MOL for HMDB0250956 (Dehydromonocrotaline)

3D SDF for HMDB0250956 (Dehydromonocrotaline)

3D-SDF for HMDB0250956 (Dehydromonocrotaline)

PDB for HMDB0250956 (Dehydromonocrotaline)

3D PDB for HMDB0250956 (Dehydromonocrotaline)

SMILES for HMDB0250956 (Dehydromonocrotaline)

INCHI for HMDB0250956 (Dehydromonocrotaline)

Structure for HMDB0250956 (Dehydromonocrotaline)

3D Structure for HMDB0250956 (Dehydromonocrotaline)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra