Jump To Section:

Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References XML

Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-11 08:06:16 UTC

Update Date

2021-09-26 23:02:41 UTC

HMDB ID

HMDB0250947

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Dehydrocrotonin

Description

5'-(furan-3-yl)-2,5-dimethyl-3,4,4a,7,8,8a-hexahydro-2H-spiro[naphthalene-1,3'-oxolane]-2',7-dione belongs to the class of organic compounds known as diterpene lactones. These are diterpenoids containing a lactone moiety. 5'-(furan-3-yl)-2,5-dimethyl-3,4,4a,7,8,8a-hexahydro-2H-spiro[naphthalene-1,3'-oxolane]-2',7-dione is an extremely weak basic (essentially neutral) compound (based on its pKa). This compound has been identified in human blood as reported by (PMID: 31557052 ). Dehydrocrotonin is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically Dehydrocrotonin 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

HMDB0250947
     RDKit          3D
Dehydrocrotonin
 45 48  0  0  0  0  0  0  0  0999 V2000
   -4.4310    1.2007    0.1031 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0302    1.4123   -0.3357 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5656    2.6408   -0.4875 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1884    2.8135   -0.9180 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8544    3.7442   -1.6621 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1817    1.8427   -0.4423 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8001    0.5686    0.0630 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0925    0.3089   -0.6291 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6744   -1.0464   -0.3274 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8970   -1.7426    0.7705 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4445   -1.8970    0.2901 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2566   -2.7408    1.2920 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1680   -0.5918   -0.0359 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3958   -0.2413    0.7288 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4620   -1.0336    0.0130 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6502   -0.1704   -0.3280 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0193    1.0210    0.2285 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1676    1.4233   -0.4108 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4557    0.5081   -1.3004 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5873   -0.4600   -1.2932 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9104   -1.4107   -1.2385 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7439   -0.6810   -1.4269 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2772   -0.2104   -2.4812 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4900    0.5704    1.0172 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9408    2.1466    0.3496 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9804    0.7334   -0.7280 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2274    3.4781   -0.2890 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3167    2.3571    0.4344 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6047    1.7051   -1.1859 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0208    0.6901    1.1540 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8842    0.3414   -1.7388 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6303   -1.7201   -1.2131 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7372   -1.0143   -0.0219 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2943   -2.7770    0.8357 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9528   -1.2416    1.7365 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5526   -2.5343   -0.6402 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0105   -3.3811    0.7619 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4965   -3.4922    1.6765 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6506   -2.2410    2.1686 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6435    0.8312    0.5366 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3629   -0.3725    1.7975 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8621   -1.8702    0.5896 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4990    1.5397    1.0213 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7375    2.3474   -0.2084 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5858   -1.3546   -1.9339 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  4  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 11 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  1  0
 15 21  1  0
 21 22  1  0
 22 23  2  0
  8  2  1  0
 22 13  1  0
 13  7  1  0
 20 16  2  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  3 27  1  0
  6 28  1  0
  6 29  1  0
  7 30  1  0
  8 31  1  0
  9 32  1  0
  9 33  1  0
 10 34  1  0
 10 35  1  0
 11 36  1  0
 12 37  1  0
 12 38  1  0
 12 39  1  0
 14 40  1  0
 14 41  1  0
 15 42  1  0
 17 43  1  0
 18 44  1  0
 20 45  1  0
M  END


  Mrv1533004191520542D          

 23 26  0  0  0  0            999 V2000
   -1.7863   -1.5844    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9969   -1.3447    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3946   -1.9084    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3948   -1.6686    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5819   -0.8651    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0205   -0.3014    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1666    0.5021    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9560    0.7419    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1430    1.5454    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5583    0.1782    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3713   -0.6253    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9736   -1.1891    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8099   -0.5412    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6200   -0.6971    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0186    0.0252    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4549    0.6275    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7078    0.2775    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1441    0.8799    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8373    0.1272    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4010   -0.4751    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1481   -0.1251    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0461    0.6936    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2360    0.8495    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  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
  8  9  2  0  0  0  0
  8 10  1  0  0  0  0
 10 11  2  0  0  0  0
  5 11  1  0  0  0  0
 11 12  1  0  0  0  0
  6 13  1  0  0  0  0
  2 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 13 17  1  0  0  0  0
 17 18  2  0  0  0  0
 15 19  1  0  0  0  0
 19 20  2  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 19 23  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0250947

> <DATABASE_NAME>
hmdb

> <SMILES>
CC1CCC2C(CC(=O)C=C2C)C11CC(OC1=O)C1=COC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C19H22O4/c1-11-7-14(20)8-16-15(11)4-3-12(2)19(16)9-17(23-18(19)21)13-5-6-22-10-13/h5-7,10,12,15-17H,3-4,8-9H2,1-2H3

> <INCHI_KEY>
PHTWCRQCDPNVLQ-UHFFFAOYSA-N

> <FORMULA>
C19H22O4

> <MOLECULAR_WEIGHT>
314.381

> <EXACT_MASS>
314.151809188

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
45

> <JCHEM_AVERAGE_POLARIZABILITY>
33.28175984975762

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
5'-(furan-3-yl)-2,5-dimethyl-3,4,4a,7,8,8a-hexahydro-2H-spiro[naphthalene-1,3'-oxolane]-2',7-dione

> <ALOGPS_LOGP>
2.96

> <JCHEM_LOGP>
3.3914534383333326

> <ALOGPS_LOGS>
-3.80

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
18.674409153728522

> <JCHEM_PKA_STRONGEST_BASIC>
-2.880701644066363

> <JCHEM_POLAR_SURFACE_AREA>
56.510000000000005

> <JCHEM_REFRACTIVITY>
85.2429

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.95e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
5'-(furan-3-yl)-2,5-dimethyl-2,3,4,4a,8,8a-hexahydrospiro[naphthalene-1,3'-oxolane]-2',7-dione

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0250947
     RDKit          3D
Dehydrocrotonin
 45 48  0  0  0  0  0  0  0  0999 V2000
   -4.4310    1.2007    0.1031 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0302    1.4123   -0.3357 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5656    2.6408   -0.4875 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1884    2.8135   -0.9180 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8544    3.7442   -1.6621 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1817    1.8427   -0.4423 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8001    0.5686    0.0630 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0925    0.3089   -0.6291 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6744   -1.0464   -0.3274 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8970   -1.7426    0.7705 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4445   -1.8970    0.2901 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2566   -2.7408    1.2920 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1680   -0.5918   -0.0359 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3958   -0.2413    0.7288 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4620   -1.0336    0.0130 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6502   -0.1704   -0.3280 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0193    1.0210    0.2285 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1676    1.4233   -0.4108 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4557    0.5081   -1.3004 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5873   -0.4600   -1.2932 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9104   -1.4107   -1.2385 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7439   -0.6810   -1.4269 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2772   -0.2104   -2.4812 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4900    0.5704    1.0172 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9408    2.1466    0.3496 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9804    0.7334   -0.7280 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2274    3.4781   -0.2890 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3167    2.3571    0.4344 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6047    1.7051   -1.1859 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0208    0.6901    1.1540 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8842    0.3414   -1.7388 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6303   -1.7201   -1.2131 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7372   -1.0143   -0.0219 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2943   -2.7770    0.8357 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9528   -1.2416    1.7365 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5526   -2.5343   -0.6402 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0105   -3.3811    0.7619 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4965   -3.4922    1.6765 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6506   -2.2410    2.1686 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6435    0.8312    0.5366 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3629   -0.3725    1.7975 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8621   -1.8702    0.5896 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4990    1.5397    1.0213 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7375    2.3474   -0.2084 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5858   -1.3546   -1.9339 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  4  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 11 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  1  0
 15 21  1  0
 21 22  1  0
 22 23  2  0
  8  2  1  0
 22 13  1  0
 13  7  1  0
 20 16  2  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  3 27  1  0
  6 28  1  0
  6 29  1  0
  7 30  1  0
  8 31  1  0
  9 32  1  0
  9 33  1  0
 10 34  1  0
 10 35  1  0
 11 36  1  0
 12 37  1  0
 12 38  1  0
 12 39  1  0
 14 40  1  0
 14 41  1  0
 15 42  1  0
 17 43  1  0
 18 44  1  0
 20 45  1  0
M  END

HEADER    PROTEIN                                 19-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   19-APR-15         0                                  
HETATM    1  C   UNK     0      -3.334  -2.958   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.861  -2.510   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -0.736  -3.562   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.737  -3.115   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.086  -1.615   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -0.038  -0.563   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.311   0.937   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.784   1.385   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       2.134   2.885   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       2.909   0.333   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.560  -1.167   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       3.684  -2.220   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -1.512  -1.010   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -3.024  -1.301   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -3.768   0.047   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      -2.716   1.171   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0      -1.321   0.518   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      -0.269   1.642   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0      -5.296   0.237   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -6.349  -0.887   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      -7.743  -0.234   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0      -7.553   1.295   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -6.040   1.586   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   13                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6   11                                                  
CONECT    6    5    7   13                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11                                                       
CONECT   11   10    5   12                                                  
CONECT   12   11                                                            
CONECT   13    6    2   14   17                                             
CONECT   14   13   15                                                       
CONECT   15   14   16   19                                                  
CONECT   16   15   17                                                       
CONECT   17   16   13   18                                                  
CONECT   18   17                                                            
CONECT   19   15   20   23                                                  
CONECT   20   19   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   19                                                       
MASTER        0    0    0    0    0    0    0    0   23    0   52    0
END

COMPND    HMDB0250947
HETATM    1  C1  UNL     1      -4.431   1.201   0.103  1.00  0.00           C  
HETATM    2  C2  UNL     1      -3.030   1.412  -0.336  1.00  0.00           C  
HETATM    3  C3  UNL     1      -2.566   2.641  -0.487  1.00  0.00           C  
HETATM    4  C4  UNL     1      -1.188   2.813  -0.918  1.00  0.00           C  
HETATM    5  O1  UNL     1      -0.854   3.744  -1.662  1.00  0.00           O  
HETATM    6  C5  UNL     1      -0.182   1.843  -0.442  1.00  0.00           C  
HETATM    7  C6  UNL     1      -0.800   0.569   0.063  1.00  0.00           C  
HETATM    8  C7  UNL     1      -2.093   0.309  -0.629  1.00  0.00           C  
HETATM    9  C8  UNL     1      -2.674  -1.046  -0.327  1.00  0.00           C  
HETATM   10  C9  UNL     1      -1.897  -1.743   0.771  1.00  0.00           C  
HETATM   11  C10 UNL     1      -0.445  -1.897   0.290  1.00  0.00           C  
HETATM   12  C11 UNL     1       0.257  -2.741   1.292  1.00  0.00           C  
HETATM   13  C12 UNL     1       0.168  -0.592  -0.036  1.00  0.00           C  
HETATM   14  C13 UNL     1       1.396  -0.241   0.729  1.00  0.00           C  
HETATM   15  C14 UNL     1       2.462  -1.034   0.013  1.00  0.00           C  
HETATM   16  C15 UNL     1       3.650  -0.170  -0.328  1.00  0.00           C  
HETATM   17  C16 UNL     1       4.019   1.021   0.229  1.00  0.00           C  
HETATM   18  C17 UNL     1       5.168   1.423  -0.411  1.00  0.00           C  
HETATM   19  O2  UNL     1       5.456   0.508  -1.300  1.00  0.00           O  
HETATM   20  C18 UNL     1       4.587  -0.460  -1.293  1.00  0.00           C  
HETATM   21  O3  UNL     1       1.910  -1.411  -1.238  1.00  0.00           O  
HETATM   22  C19 UNL     1       0.744  -0.681  -1.427  1.00  0.00           C  
HETATM   23  O4  UNL     1       0.277  -0.210  -2.481  1.00  0.00           O  
HETATM   24  H1  UNL     1      -4.490   0.570   1.017  1.00  0.00           H  
HETATM   25  H2  UNL     1      -4.941   2.147   0.350  1.00  0.00           H  
HETATM   26  H3  UNL     1      -4.980   0.733  -0.728  1.00  0.00           H  
HETATM   27  H4  UNL     1      -3.227   3.478  -0.289  1.00  0.00           H  
HETATM   28  H5  UNL     1       0.317   2.357   0.434  1.00  0.00           H  
HETATM   29  H6  UNL     1       0.605   1.705  -1.186  1.00  0.00           H  
HETATM   30  H7  UNL     1      -1.021   0.690   1.154  1.00  0.00           H  
HETATM   31  H8  UNL     1      -1.884   0.341  -1.739  1.00  0.00           H  
HETATM   32  H9  UNL     1      -2.630  -1.720  -1.213  1.00  0.00           H  
HETATM   33  H10 UNL     1      -3.737  -1.014  -0.022  1.00  0.00           H  
HETATM   34  H11 UNL     1      -2.294  -2.777   0.836  1.00  0.00           H  
HETATM   35  H12 UNL     1      -1.953  -1.242   1.737  1.00  0.00           H  
HETATM   36  H13 UNL     1      -0.553  -2.534  -0.640  1.00  0.00           H  
HETATM   37  H14 UNL     1       1.011  -3.381   0.762  1.00  0.00           H  
HETATM   38  H15 UNL     1      -0.497  -3.492   1.677  1.00  0.00           H  
HETATM   39  H16 UNL     1       0.651  -2.241   2.169  1.00  0.00           H  
HETATM   40  H17 UNL     1       1.643   0.831   0.537  1.00  0.00           H  
HETATM   41  H18 UNL     1       1.363  -0.373   1.798  1.00  0.00           H  
HETATM   42  H19 UNL     1       2.862  -1.870   0.590  1.00  0.00           H  
HETATM   43  H20 UNL     1       3.499   1.540   1.021  1.00  0.00           H  
HETATM   44  H21 UNL     1       5.738   2.347  -0.208  1.00  0.00           H  
HETATM   45  H22 UNL     1       4.586  -1.355  -1.934  1.00  0.00           H  
CONECT    1    2   24   25   26
CONECT    2    3    3    8
CONECT    3    4   27
CONECT    4    5    5    6
CONECT    6    7   28   29
CONECT    7    8   13   30
CONECT    8    9   31
CONECT    9   10   32   33
CONECT   10   11   34   35
CONECT   11   12   13   36
CONECT   12   37   38   39
CONECT   13   14   22
CONECT   14   15   40   41
CONECT   15   16   21   42
CONECT   16   17   20   20
CONECT   17   18   18   43
CONECT   18   19   44
CONECT   19   20
CONECT   20   45
CONECT   21   22
CONECT   22   23   23
END

HMDB0250947
     RDKit          3D
Dehydrocrotonin
 45 48  0  0  0  0  0  0  0  0999 V2000
   -4.4310    1.2007    0.1031 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0302    1.4123   -0.3357 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5656    2.6408   -0.4875 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1884    2.8135   -0.9180 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8544    3.7442   -1.6621 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1817    1.8427   -0.4423 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8001    0.5686    0.0630 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0925    0.3089   -0.6291 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6744   -1.0464   -0.3274 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8970   -1.7426    0.7705 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4445   -1.8970    0.2901 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2566   -2.7408    1.2920 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1680   -0.5918   -0.0359 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3958   -0.2413    0.7288 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4620   -1.0336    0.0130 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6502   -0.1704   -0.3280 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0193    1.0210    0.2285 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1676    1.4233   -0.4108 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4557    0.5081   -1.3004 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5873   -0.4600   -1.2932 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9104   -1.4107   -1.2385 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7439   -0.6810   -1.4269 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2772   -0.2104   -2.4812 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4900    0.5704    1.0172 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9408    2.1466    0.3496 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9804    0.7334   -0.7280 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2274    3.4781   -0.2890 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3167    2.3571    0.4344 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6047    1.7051   -1.1859 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0208    0.6901    1.1540 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8842    0.3414   -1.7388 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6303   -1.7201   -1.2131 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7372   -1.0143   -0.0219 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2943   -2.7770    0.8357 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9528   -1.2416    1.7365 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5526   -2.5343   -0.6402 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0105   -3.3811    0.7619 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4965   -3.4922    1.6765 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6506   -2.2410    2.1686 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6435    0.8312    0.5366 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3629   -0.3725    1.7975 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8621   -1.8702    0.5896 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4990    1.5397    1.0213 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7375    2.3474   -0.2084 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5858   -1.3546   -1.9339 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  4  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 11 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  1  0
 15 21  1  0
 21 22  1  0
 22 23  2  0
  8  2  1  0
 22 13  1  0
 13  7  1  0
 20 16  2  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  3 27  1  0
  6 28  1  0
  6 29  1  0
  7 30  1  0
  8 31  1  0
  9 32  1  0
  9 33  1  0
 10 34  1  0
 10 35  1  0
 11 36  1  0
 12 37  1  0
 12 38  1  0
 12 39  1  0
 14 40  1  0
 14 41  1  0
 15 42  1  0
 17 43  1  0
 18 44  1  0
 20 45  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Not Available

Chemical Formula

C₁₉H₂₂O₄

Average Molecular Weight

314.381

Monoisotopic Molecular Weight

314.151809188

IUPAC Name

5'-(furan-3-yl)-2,5-dimethyl-3,4,4a,7,8,8a-hexahydro-2H-spiro[naphthalene-1,3'-oxolane]-2',7-dione

Traditional Name

5'-(furan-3-yl)-2,5-dimethyl-2,3,4,4a,8,8a-hexahydrospiro[naphthalene-1,3'-oxolane]-2',7-dione

CAS Registry Number

Not Available

SMILES

CC1CCC2C(CC(=O)C=C2C)C11CC(OC1=O)C1=COC=C1

InChI Identifier

InChI=1S/C19H22O4/c1-11-7-14(20)8-16-15(11)4-3-12(2)19(16)9-17(23-18(19)21)13-5-6-22-10-13/h5-7,10,12,15-17H,3-4,8-9H2,1-2H3

InChI Key

PHTWCRQCDPNVLQ-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as diterpene lactones. These are diterpenoids containing a lactone moiety.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Terpene lactones

Direct Parent

Diterpene lactones

Alternative Parents

Substituents

Diterpene lactone
Diterpenoid
Clerodane diterpenoid
Cyclohexenone
Gamma butyrolactone
Heteroaromatic compound
Furan
Oxolane
Carboxylic acid ester
Cyclic ketone
Ketone
Lactone
Carboxylic acid derivative
Oxacycle
Organoheterocyclic compound
Monocarboxylic acid or derivatives
Hydrocarbon derivative
Organic oxide
Carbonyl group
Organooxygen compound
Organic oxygen 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)

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	2.96	ALOGPS
logP	3.39	ChemAxon
logS	-3.8	ALOGPS
pKa (Strongest Acidic)	18.67	ChemAxon
pKa (Strongest Basic)	-2.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	56.51 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	85.24 m³·mol⁻¹	ChemAxon
Polarizability	33.28 Å³	ChemAxon
Number of Rings	4	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]-	207.17	30932474
DeepCCS	[M+Na]+	182.506	30932474
AllCCS	[M+H]+	175.8	32859911
AllCCS	[M+H-H2O]+	172.5	32859911
AllCCS	[M+NH4]+	178.8	32859911
AllCCS	[M+Na]+	179.7	32859911
AllCCS	[M-H]-	182.2	32859911
AllCCS	[M+Na-2H]-	182.0	32859911
AllCCS	[M+HCOO]-	181.9	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Dehydrocrotonin	CC1CCC2C(CC(=O)C=C2C)C11CC(OC1=O)C1=COC=C1	3745.1	Standard polar	33892256
Dehydrocrotonin	CC1CCC2C(CC(=O)C=C2C)C11CC(OC1=O)C1=COC=C1	2520.0	Standard non polar	33892256
Dehydrocrotonin	CC1CCC2C(CC(=O)C=C2C)C11CC(OC1=O)C1=COC=C1	2780.4	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Dehydrocrotonin,1TMS,isomer #1	CC1=CC(O[Si](C)(C)C)=CC2C1CCC(C)C21CC(C2=COC=C2)OC1=O	2690.3	Semi standard non polar	33892256
Dehydrocrotonin,1TMS,isomer #1	CC1=CC(O[Si](C)(C)C)=CC2C1CCC(C)C21CC(C2=COC=C2)OC1=O	2561.3	Standard non polar	33892256
Dehydrocrotonin,1TMS,isomer #1	CC1=CC(O[Si](C)(C)C)=CC2C1CCC(C)C21CC(C2=COC=C2)OC1=O	3166.0	Standard polar	33892256
Dehydrocrotonin,1TBDMS,isomer #1	CC1=CC(O[Si](C)(C)C(C)(C)C)=CC2C1CCC(C)C21CC(C2=COC=C2)OC1=O	2900.9	Semi standard non polar	33892256
Dehydrocrotonin,1TBDMS,isomer #1	CC1=CC(O[Si](C)(C)C(C)(C)C)=CC2C1CCC(C)C21CC(C2=COC=C2)OC1=O	2818.6	Standard non polar	33892256
Dehydrocrotonin,1TBDMS,isomer #1	CC1=CC(O[Si](C)(C)C(C)(C)C)=CC2C1CCC(C)C21CC(C2=COC=C2)OC1=O	3281.4	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Dehydrocrotonin GC-MS (Non-derivatized) - 70eV, Positive	splash10-00gi-5960000000-db8b4ed51b5441dd1791	2021-09-24	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Dehydrocrotonin GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	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 - Dehydrocrotonin 10V, Positive-QTOF	splash10-014i-0009000000-94c839719c28eb6a5bbf	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dehydrocrotonin 20V, Positive-QTOF	splash10-014i-0195000000-b308db89295ce2d61837	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dehydrocrotonin 40V, Positive-QTOF	splash10-00ks-3980000000-b68e1fd9a9cda892741b	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dehydrocrotonin 10V, Negative-QTOF	splash10-03di-0009000000-39b39050eae413a9d507	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dehydrocrotonin 20V, Negative-QTOF	splash10-03di-2029000000-ddf5e41feec965d414a4	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dehydrocrotonin 40V, Negative-QTOF	splash10-029b-6942000000-4b482543d4f9cc53ae07	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

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

14313505

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 Dehydrocrotonin (HMDB0250947)

MOL for HMDB0250947 (Dehydrocrotonin)

3D MOL for HMDB0250947 (Dehydrocrotonin)

3D SDF for HMDB0250947 (Dehydrocrotonin)

3D-SDF for HMDB0250947 (Dehydrocrotonin)

PDB for HMDB0250947 (Dehydrocrotonin)

3D PDB for HMDB0250947 (Dehydrocrotonin)

SMILES for HMDB0250947 (Dehydrocrotonin)

INCHI for HMDB0250947 (Dehydrocrotonin)

Structure for HMDB0250947 (Dehydrocrotonin)

3D Structure for HMDB0250947 (Dehydrocrotonin)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra