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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-11 15:10:47 UTC

Update Date

2021-09-26 23:10:25 UTC

HMDB ID

HMDB0255528

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Neopetasin

Description

1,8a-dimethyl-6-oxo-7-(prop-1-en-2-yl)-1,2,3,4,6,7,8,8a-octahydronaphthalen-2-yl 2-methylbut-2-enoate belongs to the class of organic compounds known as eremophilane, 8,9-secoeremophilane and furoeremophilane sesquiterpenoids. These are sesquiterpenoids with a structure based either on the eremophilane skeleton, its 8,9-seco derivative, or the furoeremophilane skeleton. Eremophilanes have been shown to be derived from eudesmanes by migration of the methyl group at C-10 to C-5. Based on a literature review very few articles have been published on 1,8a-dimethyl-6-oxo-7-(prop-1-en-2-yl)-1,2,3,4,6,7,8,8a-octahydronaphthalen-2-yl 2-methylbut-2-enoate. This compound has been identified in human blood as reported by (PMID: 31557052 ). Neopetasin is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically Neopetasin 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

HMDB0255528
     RDKit          3D
Neopetasin
 51 52  0  0  0  0  0  0  0  0999 V2000
   -5.0837    1.1925    0.4836 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9280    1.3737    1.0965 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4437    2.7744    1.3937 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0135    0.2939    1.5496 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6001    0.5218    1.0363 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3851   -0.1833   -0.2924 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3857    0.3050   -1.3086 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5800   -1.6160   -0.0647 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5804   -2.0315    0.6778 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4896   -1.0679    1.2708 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6660   -1.3807    1.5472 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6894   -2.6663   -0.6345 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7165   -2.2043   -0.7958 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9994   -0.8567   -0.1752 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2685   -0.4369   -0.6648 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3377   -0.1304    0.1881 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0590   -0.2644    1.4112 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6247    0.2958   -0.3217 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8219    0.4139   -1.7818 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6024    0.5733    0.4926 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4318    0.4621    1.9703 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0030    0.1470   -0.7653 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1842    0.0675   -2.2599 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6514    2.1041    0.2134 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5326    0.2564    0.2150 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3375    3.4038    1.6027 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8249    2.7893    2.3100 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8319    3.1740    0.5651 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0223    0.3850    2.6826 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4157    1.6015    0.9760 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9046    0.1014    1.7856 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3351   -0.3038   -1.2559 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9500    0.2146   -2.3327 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6914    1.3539   -1.1314 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7275   -3.1186    0.8496 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7420   -3.6010   -0.0262 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0966   -2.9284   -1.6316 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0764   -2.1869   -1.8444 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3960   -2.9371   -0.2713 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9475   -0.9119    0.9103 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0329    1.1348   -2.1432 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7912    0.8605   -2.0522 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6209   -0.5372   -2.3152 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5541    0.8908    0.0610 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3794    0.8171    2.4367 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2055   -0.5798    2.2110 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6500    1.1313    2.3502 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3084    1.1379   -0.3602 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3024    0.0336   -2.4427 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2607   -0.8582   -2.6222 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1384    0.9900   -2.7928 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  6  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
  8 12  1  0
 12 13  1  0
 13 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  2  3
 20 21  1  0
 14 22  1  0
 22 23  1  0
 10  4  1  0
 22  6  1  0
  1 24  1  0
  1 25  1  0
  3 26  1  0
  3 27  1  0
  3 28  1  0
  4 29  1  0
  5 30  1  0
  5 31  1  0
  7 32  1  0
  7 33  1  0
  7 34  1  0
  9 35  1  0
 12 36  1  0
 12 37  1  0
 13 38  1  0
 13 39  1  0
 14 40  1  0
 19 41  1  0
 19 42  1  0
 19 43  1  0
 20 44  1  0
 21 45  1  0
 21 46  1  0
 21 47  1  0
 22 48  1  0
 23 49  1  0
 23 50  1  0
 23 51  1  0
M  END

  Mrv1533004181503312D          

 23 24  0  0  0  0            999 V2000
   -2.1434   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  4  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  3  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  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
 13 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 11 17  1  0  0  0  0
 17 18  1  0  0  0  0
 17 19  1  0  0  0  0
  8 19  1  0  0  0  0
 19 20  1  0  0  0  0
 15 21  1  0  0  0  0
 21 22  2  0  0  0  0
 21 23  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0255528

> <DATABASE_NAME>
hmdb

> <SMILES>
CC=C(C)C(=O)OC1CCC2=CC(=O)C(CC2(C)C1C)C(C)=C

> <INCHI_IDENTIFIER>
InChI=1S/C20H28O3/c1-7-13(4)19(22)23-18-9-8-15-10-17(21)16(12(2)3)11-20(15,6)14(18)5/h7,10,14,16,18H,2,8-9,11H2,1,3-6H3

> <INCHI_KEY>
ISTBXSFGFOYLTM-UHFFFAOYSA-N

> <FORMULA>
C20H28O3

> <MOLECULAR_WEIGHT>
316.441

> <EXACT_MASS>
316.203844762

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
51

> <JCHEM_AVERAGE_POLARIZABILITY>
36.397338215888375

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
1,8a-dimethyl-6-oxo-7-(prop-1-en-2-yl)-1,2,3,4,6,7,8,8a-octahydronaphthalen-2-yl 2-methylbut-2-enoate

> <ALOGPS_LOGP>
5.16

> <JCHEM_LOGP>
4.859976432333334

> <ALOGPS_LOGS>
-4.66

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
18.874099011678208

> <JCHEM_PKA_STRONGEST_ACIDIC>
17.093720806334645

> <JCHEM_PKA_STRONGEST_BASIC>
-5.0231006378263645

> <JCHEM_POLAR_SURFACE_AREA>
43.370000000000005

> <JCHEM_REFRACTIVITY>
93.51870000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.94e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
1,8a-dimethyl-6-oxo-7-(prop-1-en-2-yl)-1,2,3,4,7,8-hexahydronaphthalen-2-yl 2-methylbut-2-enoate

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0255528
     RDKit          3D
Neopetasin
 51 52  0  0  0  0  0  0  0  0999 V2000
   -5.0837    1.1925    0.4836 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9280    1.3737    1.0965 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4437    2.7744    1.3937 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0135    0.2939    1.5496 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6001    0.5218    1.0363 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3851   -0.1833   -0.2924 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3857    0.3050   -1.3086 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5800   -1.6160   -0.0647 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5804   -2.0315    0.6778 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4896   -1.0679    1.2708 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6660   -1.3807    1.5472 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6894   -2.6663   -0.6345 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7165   -2.2043   -0.7958 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9994   -0.8567   -0.1752 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2685   -0.4369   -0.6648 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3377   -0.1304    0.1881 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0590   -0.2644    1.4112 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6247    0.2958   -0.3217 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8219    0.4139   -1.7818 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6024    0.5733    0.4926 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4318    0.4621    1.9703 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0030    0.1470   -0.7653 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1842    0.0675   -2.2599 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6514    2.1041    0.2134 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5326    0.2564    0.2150 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3375    3.4038    1.6027 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8249    2.7893    2.3100 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8319    3.1740    0.5651 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0223    0.3850    2.6826 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4157    1.6015    0.9760 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9046    0.1014    1.7856 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3351   -0.3038   -1.2559 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9500    0.2146   -2.3327 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6914    1.3539   -1.1314 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7275   -3.1186    0.8496 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7420   -3.6010   -0.0262 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0966   -2.9284   -1.6316 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0764   -2.1869   -1.8444 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3960   -2.9371   -0.2713 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9475   -0.9119    0.9103 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0329    1.1348   -2.1432 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7912    0.8605   -2.0522 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6209   -0.5372   -2.3152 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5541    0.8908    0.0610 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3794    0.8171    2.4367 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2055   -0.5798    2.2110 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6500    1.1313    2.3502 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3084    1.1379   -0.3602 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3024    0.0336   -2.4427 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2607   -0.8582   -2.6222 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1384    0.9900   -2.7928 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  6  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
  8 12  1  0
 12 13  1  0
 13 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  2  3
 20 21  1  0
 14 22  1  0
 22 23  1  0
 10  4  1  0
 22  6  1  0
  1 24  1  0
  1 25  1  0
  3 26  1  0
  3 27  1  0
  3 28  1  0
  4 29  1  0
  5 30  1  0
  5 31  1  0
  7 32  1  0
  7 33  1  0
  7 34  1  0
  9 35  1  0
 12 36  1  0
 12 37  1  0
 13 38  1  0
 13 39  1  0
 14 40  1  0
 19 41  1  0
 19 42  1  0
 19 43  1  0
 20 44  1  0
 21 45  1  0
 21 46  1  0
 21 47  1  0
 22 48  1  0
 23 49  1  0
 23 50  1  0
 23 51  1  0
M  END

HEADER    PROTEIN                                 18-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   18-APR-15         0                                  
HETATM    1  C   UNK     0      -4.001  -5.390   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -2.667  -4.620   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -1.334  -5.390   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -1.334  -6.930   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.000  -4.620   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       1.334  -5.390   0.000  0.00  0.00           O+0
HETATM    7  O   UNK     0       0.000  -3.080   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       8.002  -0.000   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       4.001  -3.850   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       2.667  -4.620   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       8.002  -3.080   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       8.002  -4.620   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       9.336  -2.310   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8                                                       
CONECT    8    7    9   19                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12   17                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13   16   21                                                  
CONECT   16   15   17                                                       
CONECT   17   16   11   18   19                                             
CONECT   18   17                                                            
CONECT   19   17    8   20                                                  
CONECT   20   19                                                            
CONECT   21   15   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21                                                            
MASTER        0    0    0    0    0    0    0    0   23    0   48    0
END

COMPND    HMDB0255528
HETATM    1  C1  UNL     1      -5.084   1.192   0.484  1.00  0.00           C  
HETATM    2  C2  UNL     1      -3.928   1.374   1.096  1.00  0.00           C  
HETATM    3  C3  UNL     1      -3.444   2.774   1.394  1.00  0.00           C  
HETATM    4  C4  UNL     1      -3.013   0.294   1.550  1.00  0.00           C  
HETATM    5  C5  UNL     1      -1.600   0.522   1.036  1.00  0.00           C  
HETATM    6  C6  UNL     1      -1.385  -0.183  -0.292  1.00  0.00           C  
HETATM    7  C7  UNL     1      -2.386   0.305  -1.309  1.00  0.00           C  
HETATM    8  C8  UNL     1      -1.580  -1.616  -0.065  1.00  0.00           C  
HETATM    9  C9  UNL     1      -2.580  -2.031   0.678  1.00  0.00           C  
HETATM   10  C10 UNL     1      -3.490  -1.068   1.271  1.00  0.00           C  
HETATM   11  O1  UNL     1      -4.666  -1.381   1.547  1.00  0.00           O  
HETATM   12  C11 UNL     1      -0.689  -2.666  -0.635  1.00  0.00           C  
HETATM   13  C12 UNL     1       0.717  -2.204  -0.796  1.00  0.00           C  
HETATM   14  C13 UNL     1       0.999  -0.857  -0.175  1.00  0.00           C  
HETATM   15  O2  UNL     1       2.269  -0.437  -0.665  1.00  0.00           O  
HETATM   16  C14 UNL     1       3.338  -0.130   0.188  1.00  0.00           C  
HETATM   17  O3  UNL     1       3.059  -0.264   1.411  1.00  0.00           O  
HETATM   18  C15 UNL     1       4.625   0.296  -0.322  1.00  0.00           C  
HETATM   19  C16 UNL     1       4.822   0.414  -1.782  1.00  0.00           C  
HETATM   20  C17 UNL     1       5.602   0.573   0.493  1.00  0.00           C  
HETATM   21  C18 UNL     1       5.432   0.462   1.970  1.00  0.00           C  
HETATM   22  C19 UNL     1      -0.003   0.147  -0.765  1.00  0.00           C  
HETATM   23  C20 UNL     1       0.184   0.068  -2.260  1.00  0.00           C  
HETATM   24  H1  UNL     1      -5.651   2.104   0.213  1.00  0.00           H  
HETATM   25  H2  UNL     1      -5.533   0.256   0.215  1.00  0.00           H  
HETATM   26  H3  UNL     1      -4.337   3.404   1.603  1.00  0.00           H  
HETATM   27  H4  UNL     1      -2.825   2.789   2.310  1.00  0.00           H  
HETATM   28  H5  UNL     1      -2.832   3.174   0.565  1.00  0.00           H  
HETATM   29  H6  UNL     1      -3.022   0.385   2.683  1.00  0.00           H  
HETATM   30  H7  UNL     1      -1.416   1.601   0.976  1.00  0.00           H  
HETATM   31  H8  UNL     1      -0.905   0.101   1.786  1.00  0.00           H  
HETATM   32  H9  UNL     1      -3.335  -0.304  -1.256  1.00  0.00           H  
HETATM   33  H10 UNL     1      -1.950   0.215  -2.333  1.00  0.00           H  
HETATM   34  H11 UNL     1      -2.691   1.354  -1.131  1.00  0.00           H  
HETATM   35  H12 UNL     1      -2.728  -3.119   0.850  1.00  0.00           H  
HETATM   36  H13 UNL     1      -0.742  -3.601  -0.026  1.00  0.00           H  
HETATM   37  H14 UNL     1      -1.097  -2.928  -1.632  1.00  0.00           H  
HETATM   38  H15 UNL     1       1.076  -2.187  -1.844  1.00  0.00           H  
HETATM   39  H16 UNL     1       1.396  -2.937  -0.271  1.00  0.00           H  
HETATM   40  H17 UNL     1       0.948  -0.912   0.910  1.00  0.00           H  
HETATM   41  H18 UNL     1       4.033   1.135  -2.143  1.00  0.00           H  
HETATM   42  H19 UNL     1       5.791   0.861  -2.052  1.00  0.00           H  
HETATM   43  H20 UNL     1       4.621  -0.537  -2.315  1.00  0.00           H  
HETATM   44  H21 UNL     1       6.554   0.891   0.061  1.00  0.00           H  
HETATM   45  H22 UNL     1       6.379   0.817   2.437  1.00  0.00           H  
HETATM   46  H23 UNL     1       5.206  -0.580   2.211  1.00  0.00           H  
HETATM   47  H24 UNL     1       4.650   1.131   2.350  1.00  0.00           H  
HETATM   48  H25 UNL     1       0.308   1.138  -0.360  1.00  0.00           H  
HETATM   49  H26 UNL     1       1.302   0.034  -2.443  1.00  0.00           H  
HETATM   50  H27 UNL     1      -0.261  -0.858  -2.622  1.00  0.00           H  
HETATM   51  H28 UNL     1      -0.138   0.990  -2.793  1.00  0.00           H  
CONECT    1    2    2   24   25
CONECT    2    3    4
CONECT    3   26   27   28
CONECT    4    5   10   29
CONECT    5    6   30   31
CONECT    6    7    8   22
CONECT    7   32   33   34
CONECT    8    9    9   12
CONECT    9   10   35
CONECT   10   11   11
CONECT   12   13   36   37
CONECT   13   14   38   39
CONECT   14   15   22   40
CONECT   15   16
CONECT   16   17   17   18
CONECT   18   19   20   20
CONECT   19   41   42   43
CONECT   20   21   44
CONECT   21   45   46   47
CONECT   22   23   48
CONECT   23   49   50   51
END

HMDB0255528
     RDKit          3D
Neopetasin
 51 52  0  0  0  0  0  0  0  0999 V2000
   -5.0837    1.1925    0.4836 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9280    1.3737    1.0965 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4437    2.7744    1.3937 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0135    0.2939    1.5496 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6001    0.5218    1.0363 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3851   -0.1833   -0.2924 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3857    0.3050   -1.3086 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5800   -1.6160   -0.0647 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5804   -2.0315    0.6778 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4896   -1.0679    1.2708 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6660   -1.3807    1.5472 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6894   -2.6663   -0.6345 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7165   -2.2043   -0.7958 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9994   -0.8567   -0.1752 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2685   -0.4369   -0.6648 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3377   -0.1304    0.1881 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0590   -0.2644    1.4112 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6247    0.2958   -0.3217 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8219    0.4139   -1.7818 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6024    0.5733    0.4926 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4318    0.4621    1.9703 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0030    0.1470   -0.7653 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1842    0.0675   -2.2599 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6514    2.1041    0.2134 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5326    0.2564    0.2150 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3375    3.4038    1.6027 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8249    2.7893    2.3100 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8319    3.1740    0.5651 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0223    0.3850    2.6826 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4157    1.6015    0.9760 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9046    0.1014    1.7856 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3351   -0.3038   -1.2559 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9500    0.2146   -2.3327 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6914    1.3539   -1.1314 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7275   -3.1186    0.8496 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7420   -3.6010   -0.0262 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0966   -2.9284   -1.6316 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0764   -2.1869   -1.8444 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3960   -2.9371   -0.2713 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9475   -0.9119    0.9103 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0329    1.1348   -2.1432 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7912    0.8605   -2.0522 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6209   -0.5372   -2.3152 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5541    0.8908    0.0610 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3794    0.8171    2.4367 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2055   -0.5798    2.2110 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6500    1.1313    2.3502 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3084    1.1379   -0.3602 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3024    0.0336   -2.4427 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2607   -0.8582   -2.6222 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1384    0.9900   -2.7928 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  6  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
  8 12  1  0
 12 13  1  0
 13 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  2  3
 20 21  1  0
 14 22  1  0
 22 23  1  0
 10  4  1  0
 22  6  1  0
  1 24  1  0
  1 25  1  0
  3 26  1  0
  3 27  1  0
  3 28  1  0
  4 29  1  0
  5 30  1  0
  5 31  1  0
  7 32  1  0
  7 33  1  0
  7 34  1  0
  9 35  1  0
 12 36  1  0
 12 37  1  0
 13 38  1  0
 13 39  1  0
 14 40  1  0
 19 41  1  0
 19 42  1  0
 19 43  1  0
 20 44  1  0
 21 45  1  0
 21 46  1  0
 21 47  1  0
 22 48  1  0
 23 49  1  0
 23 50  1  0
 23 51  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
1,8a-Dimethyl-6-oxo-7-(prop-1-en-2-yl)-1,2,3,4,6,7,8,8a-octahydronaphthalen-2-yl 2-methylbut-2-enoic acid	Generator

Chemical Formula

C₂₀H₂₈O₃

Average Molecular Weight

316.441

Monoisotopic Molecular Weight

316.203844762

IUPAC Name

1,8a-dimethyl-6-oxo-7-(prop-1-en-2-yl)-1,2,3,4,6,7,8,8a-octahydronaphthalen-2-yl 2-methylbut-2-enoate

Traditional Name

1,8a-dimethyl-6-oxo-7-(prop-1-en-2-yl)-1,2,3,4,7,8-hexahydronaphthalen-2-yl 2-methylbut-2-enoate

CAS Registry Number

Not Available

SMILES

CC=C(C)C(=O)OC1CCC2=CC(=O)C(CC2(C)C1C)C(C)=C

InChI Identifier

InChI=1S/C20H28O3/c1-7-13(4)19(22)23-18-9-8-15-10-17(21)16(12(2)3)11-20(15,6)14(18)5/h7,10,14,16,18H,2,8-9,11H2,1,3-6H3

InChI Key

ISTBXSFGFOYLTM-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as eremophilane, 8,9-secoeremophilane and furoeremophilane sesquiterpenoids. These are sesquiterpenoids with a structure based either on the eremophilane skeleton, its 8,9-seco derivative, or the furoeremophilane skeleton. Eremophilanes have been shown to be derived from eudesmanes by migration of the methyl group at C-10 to C-5.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Sesquiterpenoids

Direct Parent

Eremophilane, 8,9-secoeremophilane and furoeremophilane sesquiterpenoids

Alternative Parents

Substituents

Eremophilane sesquiterpenoid
Fatty acid ester
Cyclohexenone
Fatty acyl
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Cyclic ketone
Ketone
Carboxylic acid ester
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Organic oxide
Organooxygen compound
Organic oxygen compound
Carbonyl group
Hydrocarbon derivative
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic 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	5.16	ALOGPS
logP	4.86	ChemAxon
logS	-4.7	ALOGPS
pKa (Strongest Acidic)	17.09	ChemAxon
pKa (Strongest Basic)	-5	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	43.37 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	93.52 m³·mol⁻¹	ChemAxon
Polarizability	36.4 Å³	ChemAxon
Number of Rings	2	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+H]+	178.085	30932474
DeepCCS	[M-H]-	175.727	30932474
DeepCCS	[M-2H]-	209.342	30932474
DeepCCS	[M+Na]+	184.569	30932474
AllCCS	[M+H]+	178.6	32859911
AllCCS	[M+H-H2O]+	175.7	32859911
AllCCS	[M+NH4]+	181.4	32859911
AllCCS	[M+Na]+	182.1	32859911
AllCCS	[M-H]-	184.5	32859911
AllCCS	[M+Na-2H]-	184.9	32859911
AllCCS	[M+HCOO]-	185.5	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Neopetasin	CC=C(C)C(=O)OC1CCC2=CC(=O)C(CC2(C)C1C)C(C)=C	2328.8	Semi standard non polar	33892256
Neopetasin	CC=C(C)C(=O)OC1CCC2=CC(=O)C(CC2(C)C1C)C(C)=C	2328.7	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Neopetasin,1TMS,isomer #1	C=C(C)C1=C(O[Si](C)(C)C)C=C2CCC(OC(=O)C(C)=CC)C(C)C2(C)C1	2525.1	Semi standard non polar	33892256
Neopetasin,1TMS,isomer #1	C=C(C)C1=C(O[Si](C)(C)C)C=C2CCC(OC(=O)C(C)=CC)C(C)C2(C)C1	2355.3	Standard non polar	33892256
Neopetasin,1TMS,isomer #1	C=C(C)C1=C(O[Si](C)(C)C)C=C2CCC(OC(=O)C(C)=CC)C(C)C2(C)C1	2777.6	Standard polar	33892256
Neopetasin,1TBDMS,isomer #1	C=C(C)C1=C(O[Si](C)(C)C(C)(C)C)C=C2CCC(OC(=O)C(C)=CC)C(C)C2(C)C1	2755.2	Semi standard non polar	33892256
Neopetasin,1TBDMS,isomer #1	C=C(C)C1=C(O[Si](C)(C)C(C)(C)C)C=C2CCC(OC(=O)C(C)=CC)C(C)C2(C)C1	2570.4	Standard non polar	33892256
Neopetasin,1TBDMS,isomer #1	C=C(C)C1=C(O[Si](C)(C)C(C)(C)C)C=C2CCC(OC(=O)C(C)=CC)C(C)C2(C)C1	2908.1	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Neopetasin GC-MS (Non-derivatized) - 70eV, Positive	splash10-0kcs-9641000000-29fdcdc63e96146f4d0d	2021-09-23	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Neopetasin GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Neopetasin GC-MS (Non-derivatized) - 70eV, Positive	Not Available	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

2744558

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

3504628

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 Neopetasin (HMDB0255528)

MOL for HMDB0255528 (Neopetasin)

3D MOL for HMDB0255528 (Neopetasin)

3D SDF for HMDB0255528 (Neopetasin)

3D-SDF for HMDB0255528 (Neopetasin)

PDB for HMDB0255528 (Neopetasin)

3D PDB for HMDB0255528 (Neopetasin)

SMILES for HMDB0255528 (Neopetasin)

INCHI for HMDB0255528 (Neopetasin)

Structure for HMDB0255528 (Neopetasin)

3D Structure for HMDB0255528 (Neopetasin)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra