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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-11 00:13:07 UTC

Update Date

2021-09-26 22:56:45 UTC

HMDB ID

HMDB0247207

Secondary Accession Numbers

None

Metabolite Identification

Common Name

(5E)-5-[(3Ar,4S,5S,6aR)-5-hydroxy-4-[(E,3R)-3-hydroxyoct-1-enyl]-3,3a,4,5,6,6a-hexahydro-1H-pentalen-2-ylidene]pentanoic acid

Description

(5E)-5-[(3Ar,4S,5S,6aR)-5-hydroxy-4-[(E,3R)-3-hydroxyoct-1-enyl]-3,3a,4,5,6,6a-hexahydro-1H-pentalen-2-ylidene]pentanoic acid, also known as carba-prostacyclin or (5E)-6a-carba-prostaglandin I2, belongs to the class of organic compounds known as prostaglandins and related compounds. These are unsaturated carboxylic acids consisting of a 20 carbon skeleton that also contains a five member ring, and are based upon the fatty acid arachidonic acid. Based on a literature review a significant number of articles have been published on (5E)-5-[(3Ar,4S,5S,6aR)-5-hydroxy-4-[(E,3R)-3-hydroxyoct-1-enyl]-3,3a,4,5,6,6a-hexahydro-1H-pentalen-2-ylidene]pentanoic acid. This compound has been identified in human blood as reported by (PMID: 31557052 ). (5e)-5-[(3ar,4s,5s,6ar)-5-hydroxy-4-[(e,3r)-3-hydroxyoct-1-enyl]-3,3a,4,5,6,6a-hexahydro-1h-pentalen-2-ylidene]pentanoic acid is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically (5E)-5-[(3Ar,4S,5S,6aR)-5-hydroxy-4-[(E,3R)-3-hydroxyoct-1-enyl]-3,3a,4,5,6,6a-hexahydro-1H-pentalen-2-ylidene]pentanoic acid is part of the human exposome. The exposome can be defined as the collection of all the exposures of an individual in a lifetime and how those exposures relate to health. An individual's exposure begins before birth and includes insults from environmental and occupational sources.

Structure

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

  Mrv1652309112102132D          

 25 26  0  0  0  0            999 V2000
   -5.7369   -3.2234    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0224   -2.8109    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3080   -3.2234    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5935   -2.8109    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8790   -3.2234    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1645   -2.8109    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4501   -3.2234    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7356   -2.8109    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0211   -3.2234    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0651   -4.0438    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8721   -4.2154    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2846   -3.5009    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7325   -2.8878    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1450   -2.1733    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9520   -2.3449    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5651   -1.7928    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3936   -0.9858    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0067   -0.4338    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8352    0.3732    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4482    0.9252    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2767    1.7322    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2329    0.6703    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0383   -3.1653    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5480   -4.5959    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1645   -1.9859    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  7  6  1  4  0  0  0
  7  8  2  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  1  0  0  0  0
 12 13  1  0  0  0  0
  9 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 16 17  1  4  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 20 22  1  0  0  0  0
 15 23  1  0  0  0  0
 12 23  1  0  0  0  0
 10 24  1  0  0  0  0
  6 25  1  0  0  0  0
M  END

HMDB0247207
     RDKit          3D
(5E)-5-[(3Ar,4S,5S,6aR)-5-hydroxy-4-[(E,3R)-3-hydroxyoct-1-enyl]-3,3a,4,5,6,6...
 59 60  0  0  0  0  0  0  0  0999 V2000
    8.0282   -0.7620    0.2580 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1744   -0.4991   -0.9752 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7460   -0.1513   -0.5107 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1954   -1.2858    0.2571 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8693   -1.1818    0.8697 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6766   -0.9083    0.0155 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4521   -1.8256   -0.9856 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5032    0.5018   -0.3426 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3593    1.1300   -0.2791 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0706    0.5568    0.1491 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4327    1.4464    1.2791 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3952    0.8407    2.0592 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0247    2.6040    0.4812 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7618    1.8918   -0.6519 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1177    1.4667   -0.1937 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0663    0.0028   -0.0681 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8927   -0.7403    0.6475 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9993   -0.1474    1.4246 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3589   -0.6505    1.1013 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8467   -0.4744   -0.2881 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0775   -1.1325   -1.3404 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3737   -0.5589   -2.2004 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1358   -2.5314   -1.3849 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9412   -0.4932   -0.8843 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9743    0.6685   -0.9509 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9128   -1.7963    0.5819 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.8060    0.0045    1.0105 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.0975   -0.6319   -0.0685 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1764   -1.4305   -1.5756 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5717    0.3108   -1.6074 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2182    0.0560   -1.4663 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7859    0.7588    0.0902 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9242   -1.5043    1.1069 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1881   -2.2088   -0.4107 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8455   -0.4240    1.7183 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6985   -2.1553    1.4382 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7912   -1.1148    0.7452 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6655   -1.4011   -1.8379 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3570    1.1266   -0.6896 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3672    2.2127   -0.5815 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0801   -0.4941    0.4359 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4623    1.7774    1.8653 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1897   -0.1231    2.1498 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2670    3.2529    0.0433 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7246    3.2122    1.0860 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8290    2.5531   -1.5353 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8680    1.7408   -0.9627 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3658    1.9612    0.7934 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7495   -1.8127    0.6616 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7995   -0.3462    2.5260 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0286    0.9721    1.2793 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3701   -1.7493    1.3626 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1055   -0.2149    1.8303 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9254   -0.7833   -0.3022 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8170    0.6289   -0.5209 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3285   -2.9670   -2.2541 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3299   -0.6164   -1.9380 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4820   -1.4215   -0.5427 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4444    0.6952   -1.9176 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  6  8  1  0
  8  9  2  3
  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  2  3
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  2  0
 21 23  1  0
 16 24  1  0
 24 25  1  0
 25 10  1  0
 25 14  1  0
  1 26  1  0
  1 27  1  0
  1 28  1  0
  2 29  1  0
  2 30  1  0
  3 31  1  0
  3 32  1  0
  4 33  1  0
  4 34  1  0
  5 35  1  0
  5 36  1  0
  6 37  1  0
  7 38  1  0
  8 39  1  0
  9 40  1  0
 10 41  1  0
 11 42  1  0
 12 43  1  0
 13 44  1  0
 13 45  1  0
 14 46  1  0
 15 47  1  0
 15 48  1  0
 17 49  1  0
 18 50  1  0
 18 51  1  0
 19 52  1  0
 19 53  1  0
 20 54  1  0
 20 55  1  0
 23 56  1  0
 24 57  1  0
 24 58  1  0
 25 59  1  0
M  END

  Mrv1652309112102132D          

 25 26  0  0  0  0            999 V2000
   -5.7369   -3.2234    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0224   -2.8109    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3080   -3.2234    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5935   -2.8109    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8790   -3.2234    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1645   -2.8109    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4501   -3.2234    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7356   -2.8109    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0211   -3.2234    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0651   -4.0438    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8721   -4.2154    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2846   -3.5009    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7325   -2.8878    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1450   -2.1733    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9520   -2.3449    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5651   -1.7928    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3936   -0.9858    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0067   -0.4338    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8352    0.3732    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4482    0.9252    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2767    1.7322    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2329    0.6703    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0383   -3.1653    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5480   -4.5959    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1645   -1.9859    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  7  6  1  4  0  0  0
  7  8  2  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  1  0  0  0  0
 12 13  1  0  0  0  0
  9 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 16 17  1  4  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 20 22  1  0  0  0  0
 15 23  1  0  0  0  0
 12 23  1  0  0  0  0
 10 24  1  0  0  0  0
  6 25  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0247207

> <DATABASE_NAME>
hmdb

> <SMILES>
CCCCCC(O)C=CC1C(O)CC2CC(CC12)=CCCCC(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C21H34O4/c1-2-3-4-8-17(22)10-11-18-19-13-15(7-5-6-9-21(24)25)12-16(19)14-20(18)23/h7,10-11,16-20,22-23H,2-6,8-9,12-14H2,1H3,(H,24,25)

> <INCHI_KEY>
XZFRIPGNUQRGPI-UHFFFAOYSA-N

> <FORMULA>
C21H34O4

> <MOLECULAR_WEIGHT>
350.499

> <EXACT_MASS>
350.245709575

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
59

> <JCHEM_AVERAGE_POLARIZABILITY>
41.986854839349036

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
5-[5-hydroxy-4-(3-hydroxyoct-1-en-1-yl)-octahydropentalen-2-ylidene]pentanoic acid

> <ALOGPS_LOGP>
4.70

> <JCHEM_LOGP>
3.6146990206666656

> <ALOGPS_LOGS>
-3.80

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
17.680579127157383

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.6648156388362185

> <JCHEM_PKA_STRONGEST_BASIC>
-0.9228249567895571

> <JCHEM_POLAR_SURFACE_AREA>
77.76

> <JCHEM_REFRACTIVITY>
101.3492

> <JCHEM_ROTATABLE_BOND_COUNT>
10

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.51e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
5-[5-hydroxy-4-(3-hydroxyoct-1-en-1-yl)-hexahydro-1H-pentalen-2-ylidene]pentanoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0247207
     RDKit          3D
(5E)-5-[(3Ar,4S,5S,6aR)-5-hydroxy-4-[(E,3R)-3-hydroxyoct-1-enyl]-3,3a,4,5,6,6...
 59 60  0  0  0  0  0  0  0  0999 V2000
    8.0282   -0.7620    0.2580 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1744   -0.4991   -0.9752 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7460   -0.1513   -0.5107 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1954   -1.2858    0.2571 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8693   -1.1818    0.8697 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6766   -0.9083    0.0155 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4521   -1.8256   -0.9856 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5032    0.5018   -0.3426 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3593    1.1300   -0.2791 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0706    0.5568    0.1491 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4327    1.4464    1.2791 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3952    0.8407    2.0592 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0247    2.6040    0.4812 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7618    1.8918   -0.6519 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1177    1.4667   -0.1937 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0663    0.0028   -0.0681 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8927   -0.7403    0.6475 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9993   -0.1474    1.4246 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3589   -0.6505    1.1013 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8467   -0.4744   -0.2881 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0775   -1.1325   -1.3404 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3737   -0.5589   -2.2004 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1358   -2.5314   -1.3849 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9412   -0.4932   -0.8843 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9743    0.6685   -0.9509 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9128   -1.7963    0.5819 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.8060    0.0045    1.0105 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.0975   -0.6319   -0.0685 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1764   -1.4305   -1.5756 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5717    0.3108   -1.6074 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2182    0.0560   -1.4663 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7859    0.7588    0.0902 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9242   -1.5043    1.1069 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1881   -2.2088   -0.4107 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8455   -0.4240    1.7183 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6985   -2.1553    1.4382 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7912   -1.1148    0.7452 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6655   -1.4011   -1.8379 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3570    1.1266   -0.6896 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3672    2.2127   -0.5815 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0801   -0.4941    0.4359 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4623    1.7774    1.8653 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1897   -0.1231    2.1498 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2670    3.2529    0.0433 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7246    3.2122    1.0860 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8290    2.5531   -1.5353 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8680    1.7408   -0.9627 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3658    1.9612    0.7934 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7495   -1.8127    0.6616 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7995   -0.3462    2.5260 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0286    0.9721    1.2793 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3701   -1.7493    1.3626 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1055   -0.2149    1.8303 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9254   -0.7833   -0.3022 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8170    0.6289   -0.5209 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3285   -2.9670   -2.2541 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3299   -0.6164   -1.9380 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4820   -1.4215   -0.5427 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4444    0.6952   -1.9176 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  6  8  1  0
  8  9  2  3
  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  2  3
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  2  0
 21 23  1  0
 16 24  1  0
 24 25  1  0
 25 10  1  0
 25 14  1  0
  1 26  1  0
  1 27  1  0
  1 28  1  0
  2 29  1  0
  2 30  1  0
  3 31  1  0
  3 32  1  0
  4 33  1  0
  4 34  1  0
  5 35  1  0
  5 36  1  0
  6 37  1  0
  7 38  1  0
  8 39  1  0
  9 40  1  0
 10 41  1  0
 11 42  1  0
 12 43  1  0
 13 44  1  0
 13 45  1  0
 14 46  1  0
 15 47  1  0
 15 48  1  0
 17 49  1  0
 18 50  1  0
 18 51  1  0
 19 52  1  0
 19 53  1  0
 20 54  1  0
 20 55  1  0
 23 56  1  0
 24 57  1  0
 24 58  1  0
 25 59  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     -10.709  -6.017   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -9.375  -5.247   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -8.042  -6.017   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -6.708  -5.247   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -5.374  -6.017   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -4.040  -5.247   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -2.707  -6.017   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -1.373  -5.247   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -0.039  -6.017   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.122  -7.548   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.628  -7.869   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.398  -6.535   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.367  -5.391   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.137  -4.057   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       3.644  -4.377   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       4.788  -3.347   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       4.468  -1.840   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       5.612  -0.810   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       5.292   0.697   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       6.437   1.727   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       6.117   3.233   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0       7.901   1.251   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       3.805  -5.909   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0      -1.023  -8.579   0.000  0.00  0.00           O+0
HETATM   25  O   UNK     0      -4.040  -3.707   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7   25                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   13                                                  
CONECT   10    9   11   24                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13   23                                                  
CONECT   13   12    9   14                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16   23                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20                                                            
CONECT   23   15   12                                                       
CONECT   24   10                                                            
CONECT   25    6                                                            
MASTER        0    0    0    0    0    0    0    0   25    0   52    0
END

COMPND    HMDB0249605
HETATM    1  C1  UNL     1       7.016   1.549  -0.168  1.00  0.00           C  
HETATM    2  C2  UNL     1       5.650   1.533   0.437  1.00  0.00           C  
HETATM    3  C3  UNL     1       4.740   0.501  -0.271  1.00  0.00           C  
HETATM    4  C4  UNL     1       5.309  -0.863  -0.157  1.00  0.00           C  
HETATM    5  C5  UNL     1       4.552  -1.933  -0.831  1.00  0.00           C  
HETATM    6  C6  UNL     1       3.151  -2.141  -0.350  1.00  0.00           C  
HETATM    7  O1  UNL     1       2.593  -3.233  -1.080  1.00  0.00           O  
HETATM    8  C7  UNL     1       2.255  -0.963  -0.575  1.00  0.00           C  
HETATM    9  C8  UNL     1       1.235  -0.685   0.226  1.00  0.00           C  
HETATM   10  C9  UNL     1       0.384   0.462  -0.017  1.00  0.00           C  
HETATM   11  C10 UNL     1       0.365   1.451   1.160  1.00  0.00           C  
HETATM   12  O2  UNL     1       0.923   2.662   0.845  1.00  0.00           O  
HETATM   13  C11 UNL     1      -1.087   1.554   1.600  1.00  0.00           C  
HETATM   14  C12 UNL     1      -1.562   0.213   1.213  1.00  0.00           C  
HETATM   15  C13 UNL     1      -3.025   0.068   0.899  1.00  0.00           C  
HETATM   16  C14 UNL     1      -2.994  -0.986  -0.152  1.00  0.00           C  
HETATM   17  C15 UNL     1      -3.905  -1.731  -0.722  1.00  0.00           C  
HETATM   18  C16 UNL     1      -5.327  -1.766  -0.502  1.00  0.00           C  
HETATM   19  C17 UNL     1      -6.002  -0.593   0.136  1.00  0.00           C  
HETATM   20  C18 UNL     1      -5.884   0.630  -0.750  1.00  0.00           C  
HETATM   21  C19 UNL     1      -6.519   1.800  -0.102  1.00  0.00           C  
HETATM   22  O3  UNL     1      -7.054   1.687   1.026  1.00  0.00           O  
HETATM   23  O4  UNL     1      -6.537   3.037  -0.722  1.00  0.00           O  
HETATM   24  C20 UNL     1      -1.512  -1.134  -0.590  1.00  0.00           C  
HETATM   25  C21 UNL     1      -1.040   0.208  -0.245  1.00  0.00           C  
HETATM   26  H1  UNL     1       7.498   2.524   0.087  1.00  0.00           H  
HETATM   27  H2  UNL     1       7.649   0.759   0.263  1.00  0.00           H  
HETATM   28  H3  UNL     1       6.908   1.490  -1.266  1.00  0.00           H  
HETATM   29  H4  UNL     1       5.128   2.503   0.323  1.00  0.00           H  
HETATM   30  H5  UNL     1       5.693   1.196   1.496  1.00  0.00           H  
HETATM   31  H6  UNL     1       3.781   0.615   0.303  1.00  0.00           H  
HETATM   32  H7  UNL     1       4.539   0.835  -1.299  1.00  0.00           H  
HETATM   33  H8  UNL     1       5.450  -1.101   0.941  1.00  0.00           H  
HETATM   34  H9  UNL     1       6.374  -0.863  -0.549  1.00  0.00           H  
HETATM   35  H10 UNL     1       5.133  -2.908  -0.810  1.00  0.00           H  
HETATM   36  H11 UNL     1       4.453  -1.716  -1.936  1.00  0.00           H  
HETATM   37  H12 UNL     1       3.115  -2.434   0.703  1.00  0.00           H  
HETATM   38  H13 UNL     1       2.871  -4.043  -0.621  1.00  0.00           H  
HETATM   39  H14 UNL     1       2.476  -0.345  -1.438  1.00  0.00           H  
HETATM   40  H15 UNL     1       1.057  -1.338   1.064  1.00  0.00           H  
HETATM   41  H16 UNL     1       0.787   1.049  -0.873  1.00  0.00           H  
HETATM   42  H17 UNL     1       0.897   0.937   2.011  1.00  0.00           H  
HETATM   43  H18 UNL     1       1.644   2.847   1.528  1.00  0.00           H  
HETATM   44  H19 UNL     1      -1.634   2.350   1.084  1.00  0.00           H  
HETATM   45  H20 UNL     1      -1.176   1.678   2.697  1.00  0.00           H  
HETATM   46  H21 UNL     1      -1.135  -0.599   1.794  1.00  0.00           H  
HETATM   47  H22 UNL     1      -3.356   1.057   0.542  1.00  0.00           H  
HETATM   48  H23 UNL     1      -3.588  -0.253   1.810  1.00  0.00           H  
HETATM   49  H24 UNL     1      -3.521  -2.451  -1.499  1.00  0.00           H  
HETATM   50  H25 UNL     1      -5.902  -1.924  -1.484  1.00  0.00           H  
HETATM   51  H26 UNL     1      -5.642  -2.715   0.060  1.00  0.00           H  
HETATM   52  H27 UNL     1      -5.775  -0.408   1.187  1.00  0.00           H  
HETATM   53  H28 UNL     1      -7.127  -0.826   0.152  1.00  0.00           H  
HETATM   54  H29 UNL     1      -4.890   0.802  -1.150  1.00  0.00           H  
HETATM   55  H30 UNL     1      -6.543   0.403  -1.665  1.00  0.00           H  
HETATM   56  H31 UNL     1      -6.720   3.889  -0.188  1.00  0.00           H  
HETATM   57  H32 UNL     1      -1.463  -1.396  -1.649  1.00  0.00           H  
HETATM   58  H33 UNL     1      -1.145  -1.927   0.095  1.00  0.00           H  
HETATM   59  H34 UNL     1      -1.562   0.987  -0.794  1.00  0.00           H  
CONECT    1    2   26   27   28
CONECT    2    3   29   30
CONECT    3    4   31   32
CONECT    4    5   33   34
CONECT    5    6   35   36
CONECT    6    7    8   37
CONECT    7   38
CONECT    8    9    9   39
CONECT    9   10   40
CONECT   10   11   25   41
CONECT   11   12   13   42
CONECT   12   43
CONECT   13   14   44   45
CONECT   14   15   25   46
CONECT   15   16   47   48
CONECT   16   17   17   24
CONECT   17   18   49
CONECT   18   19   50   51
CONECT   19   20   52   53
CONECT   20   21   54   55
CONECT   21   22   22   23
CONECT   23   56
CONECT   24   25   57   58
CONECT   25   59
END

HMDB0247207
     RDKit          3D
(5E)-5-[(3Ar,4S,5S,6aR)-5-hydroxy-4-[(E,3R)-3-hydroxyoct-1-enyl]-3,3a,4,5,6,6...
 59 60  0  0  0  0  0  0  0  0999 V2000
    8.0282   -0.7620    0.2580 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1744   -0.4991   -0.9752 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7460   -0.1513   -0.5107 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1954   -1.2858    0.2571 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8693   -1.1818    0.8697 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6766   -0.9083    0.0155 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4521   -1.8256   -0.9856 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5032    0.5018   -0.3426 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3593    1.1300   -0.2791 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0706    0.5568    0.1491 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4327    1.4464    1.2791 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3952    0.8407    2.0592 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0247    2.6040    0.4812 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7618    1.8918   -0.6519 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1177    1.4667   -0.1937 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0663    0.0028   -0.0681 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8927   -0.7403    0.6475 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9993   -0.1474    1.4246 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3589   -0.6505    1.1013 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8467   -0.4744   -0.2881 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0775   -1.1325   -1.3404 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3737   -0.5589   -2.2004 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1358   -2.5314   -1.3849 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9412   -0.4932   -0.8843 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9743    0.6685   -0.9509 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9128   -1.7963    0.5819 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.8060    0.0045    1.0105 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.0975   -0.6319   -0.0685 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1764   -1.4305   -1.5756 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5717    0.3108   -1.6074 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2182    0.0560   -1.4663 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7859    0.7588    0.0902 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9242   -1.5043    1.1069 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1881   -2.2088   -0.4107 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8455   -0.4240    1.7183 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6985   -2.1553    1.4382 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7912   -1.1148    0.7452 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6655   -1.4011   -1.8379 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3570    1.1266   -0.6896 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3672    2.2127   -0.5815 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0801   -0.4941    0.4359 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4623    1.7774    1.8653 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1897   -0.1231    2.1498 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2670    3.2529    0.0433 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7246    3.2122    1.0860 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8290    2.5531   -1.5353 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8680    1.7408   -0.9627 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3658    1.9612    0.7934 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7495   -1.8127    0.6616 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7995   -0.3462    2.5260 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0286    0.9721    1.2793 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3701   -1.7493    1.3626 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1055   -0.2149    1.8303 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9254   -0.7833   -0.3022 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8170    0.6289   -0.5209 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3285   -2.9670   -2.2541 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3299   -0.6164   -1.9380 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4820   -1.4215   -0.5427 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4444    0.6952   -1.9176 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  6  8  1  0
  8  9  2  3
  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  2  3
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  2  0
 21 23  1  0
 16 24  1  0
 24 25  1  0
 25 10  1  0
 25 14  1  0
  1 26  1  0
  1 27  1  0
  1 28  1  0
  2 29  1  0
  2 30  1  0
  3 31  1  0
  3 32  1  0
  4 33  1  0
  4 34  1  0
  5 35  1  0
  5 36  1  0
  6 37  1  0
  7 38  1  0
  8 39  1  0
  9 40  1  0
 10 41  1  0
 11 42  1  0
 12 43  1  0
 13 44  1  0
 13 45  1  0
 14 46  1  0
 15 47  1  0
 15 48  1  0
 17 49  1  0
 18 50  1  0
 18 51  1  0
 19 52  1  0
 19 53  1  0
 20 54  1  0
 20 55  1  0
 23 56  1  0
 24 57  1  0
 24 58  1  0
 25 59  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
(5E)-5-[(3Ar,4S,5S,6ar)-5-hydroxy-4-[(e,3R)-3-hydroxyoct-1-enyl]-3,3a,4,5,6,6a-hexahydro-1H-pentalen-2-ylidene]pentanoate	Generator
(5E)-6a-Carba-prostaglandin I2	HMDB
6,9-Methano pgi2	HMDB
6,9-Methano-pgi2	HMDB
6,9-Methanoprostaglandin I2	HMDB
6a-Carba-pgi2	HMDB
9alpha-Deoxy-9alpha-methylene-pgi2	HMDB
Carba PGX	HMDB
Carba-prostacyclin	HMDB
Carbacycline	HMDB
Carbaprostacyclin	HMDB
Carboprostacyclin	HMDB
Carboprostacyclin, (3as-(2Z,3aalpha,4alpha,(1E,3R*),5beta,6aalpha))-isomer	HMDB
Carboprostacyclin, monosodium salt	HMDB

Chemical Formula

C₂₁H₃₄O₄

Average Molecular Weight

350.499

Monoisotopic Molecular Weight

350.245709575

IUPAC Name

5-[5-hydroxy-4-(3-hydroxyoct-1-en-1-yl)-octahydropentalen-2-ylidene]pentanoic acid

Traditional Name

5-[5-hydroxy-4-(3-hydroxyoct-1-en-1-yl)-hexahydro-1H-pentalen-2-ylidene]pentanoic acid

CAS Registry Number

Not Available

SMILES

CCCCCC(O)C=CC1C(O)CC2CC(CC12)=CCCCC(O)=O

InChI Identifier

InChI=1S/C21H34O4/c1-2-3-4-8-17(22)10-11-18-19-13-15(7-5-6-9-21(24)25)12-16(19)14-20(18)23/h7,10-11,16-20,22-23H,2-6,8-9,12-14H2,1H3,(H,24,25)

InChI Key

XZFRIPGNUQRGPI-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as prostaglandins and related compounds. These are unsaturated carboxylic acids consisting of a 20 carbon skeleton that also contains a five member ring, and are based upon the fatty acid arachidonic acid.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Eicosanoids

Direct Parent

Prostaglandins and related compounds

Alternative Parents

Substituents

Prostaglandin skeleton
Bicyclic monoterpenoid
Monoterpenoid
Fatty alcohol
Medium-chain hydroxy acid
Medium-chain fatty acid
Hydroxy fatty acid
Cyclic alcohol
Secondary alcohol
Monocarboxylic acid or derivatives
Carboxylic acid
Carboxylic acid derivative
Hydrocarbon derivative
Organooxygen compound
Organic oxide
Alcohol
Carbonyl group
Organic oxygen compound
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	4.7	ALOGPS
logP	3.61	ChemAxon
logS	-3.8	ALOGPS
pKa (Strongest Acidic)	4.66	ChemAxon
pKa (Strongest Basic)	-0.92	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	77.76 Å²	ChemAxon
Rotatable Bond Count	10	ChemAxon
Refractivity	101.35 m³·mol⁻¹	ChemAxon
Polarizability	41.99 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-2H]-	225.086	30932474
DeepCCS	[M+Na]+	200.651	30932474

Predicted Kovats Retention Indices

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
(5E)-5-[(3Ar,4S,5S,6aR)-5-hydroxy-4-[(E,3R)-3-hydroxyoct-1-enyl]-3,3a,4,5,6,6a-hexahydro-1H-pentalen-2-ylidene]pentanoic acid,1TMS,isomer #1	CCCCCC(C=CC1C(O)CC2CC(=CCCCC(=O)O)CC21)O[Si](C)(C)C	3022.1	Semi standard non polar	33892256
(5E)-5-[(3Ar,4S,5S,6aR)-5-hydroxy-4-[(E,3R)-3-hydroxyoct-1-enyl]-3,3a,4,5,6,6a-hexahydro-1H-pentalen-2-ylidene]pentanoic acid,1TMS,isomer #1	CCCCCC(C=CC1C(O)CC2CC(=CCCCC(=O)O)CC21)O[Si](C)(C)C	2794.5	Standard non polar	33892256
(5E)-5-[(3Ar,4S,5S,6aR)-5-hydroxy-4-[(E,3R)-3-hydroxyoct-1-enyl]-3,3a,4,5,6,6a-hexahydro-1H-pentalen-2-ylidene]pentanoic acid,1TMS,isomer #1	CCCCCC(C=CC1C(O)CC2CC(=CCCCC(=O)O)CC21)O[Si](C)(C)C	3714.9	Standard polar	33892256
(5E)-5-[(3Ar,4S,5S,6aR)-5-hydroxy-4-[(E,3R)-3-hydroxyoct-1-enyl]-3,3a,4,5,6,6a-hexahydro-1H-pentalen-2-ylidene]pentanoic acid,1TMS,isomer #2	CCCCCC(O)C=CC1C(O[Si](C)(C)C)CC2CC(=CCCCC(=O)O)CC21	2936.9	Semi standard non polar	33892256
(5E)-5-[(3Ar,4S,5S,6aR)-5-hydroxy-4-[(E,3R)-3-hydroxyoct-1-enyl]-3,3a,4,5,6,6a-hexahydro-1H-pentalen-2-ylidene]pentanoic acid,1TMS,isomer #2	CCCCCC(O)C=CC1C(O[Si](C)(C)C)CC2CC(=CCCCC(=O)O)CC21	2763.3	Standard non polar	33892256
(5E)-5-[(3Ar,4S,5S,6aR)-5-hydroxy-4-[(E,3R)-3-hydroxyoct-1-enyl]-3,3a,4,5,6,6a-hexahydro-1H-pentalen-2-ylidene]pentanoic acid,1TMS,isomer #2	CCCCCC(O)C=CC1C(O[Si](C)(C)C)CC2CC(=CCCCC(=O)O)CC21	3617.1	Standard polar	33892256
(5E)-5-[(3Ar,4S,5S,6aR)-5-hydroxy-4-[(E,3R)-3-hydroxyoct-1-enyl]-3,3a,4,5,6,6a-hexahydro-1H-pentalen-2-ylidene]pentanoic acid,2TMS,isomer #3	CCCCCC(O)C=CC1C(O[Si](C)(C)C)CC2CC(=CCCCC(=O)O[Si](C)(C)C)CC21	2843.3	Semi standard non polar	33892256
(5E)-5-[(3Ar,4S,5S,6aR)-5-hydroxy-4-[(E,3R)-3-hydroxyoct-1-enyl]-3,3a,4,5,6,6a-hexahydro-1H-pentalen-2-ylidene]pentanoic acid,2TMS,isomer #3	CCCCCC(O)C=CC1C(O[Si](C)(C)C)CC2CC(=CCCCC(=O)O[Si](C)(C)C)CC21	2867.4	Standard non polar	33892256
(5E)-5-[(3Ar,4S,5S,6aR)-5-hydroxy-4-[(E,3R)-3-hydroxyoct-1-enyl]-3,3a,4,5,6,6a-hexahydro-1H-pentalen-2-ylidene]pentanoic acid,2TMS,isomer #3	CCCCCC(O)C=CC1C(O[Si](C)(C)C)CC2CC(=CCCCC(=O)O[Si](C)(C)C)CC21	3443.1	Standard polar	33892256
(5E)-5-[(3Ar,4S,5S,6aR)-5-hydroxy-4-[(E,3R)-3-hydroxyoct-1-enyl]-3,3a,4,5,6,6a-hexahydro-1H-pentalen-2-ylidene]pentanoic acid,3TMS,isomer #1	CCCCCC(C=CC1C(O[Si](C)(C)C)CC2CC(=CCCCC(=O)O[Si](C)(C)C)CC21)O[Si](C)(C)C	2851.1	Semi standard non polar	33892256
(5E)-5-[(3Ar,4S,5S,6aR)-5-hydroxy-4-[(E,3R)-3-hydroxyoct-1-enyl]-3,3a,4,5,6,6a-hexahydro-1H-pentalen-2-ylidene]pentanoic acid,3TMS,isomer #1	CCCCCC(C=CC1C(O[Si](C)(C)C)CC2CC(=CCCCC(=O)O[Si](C)(C)C)CC21)O[Si](C)(C)C	2906.9	Standard non polar	33892256
(5E)-5-[(3Ar,4S,5S,6aR)-5-hydroxy-4-[(E,3R)-3-hydroxyoct-1-enyl]-3,3a,4,5,6,6a-hexahydro-1H-pentalen-2-ylidene]pentanoic acid,3TMS,isomer #1	CCCCCC(C=CC1C(O[Si](C)(C)C)CC2CC(=CCCCC(=O)O[Si](C)(C)C)CC21)O[Si](C)(C)C	3145.7	Standard polar	33892256
(5E)-5-[(3Ar,4S,5S,6aR)-5-hydroxy-4-[(E,3R)-3-hydroxyoct-1-enyl]-3,3a,4,5,6,6a-hexahydro-1H-pentalen-2-ylidene]pentanoic acid,1TBDMS,isomer #3	CCCCCC(O)C=CC1C(O)CC2CC(=CCCCC(=O)O[Si](C)(C)C(C)(C)C)CC21	3171.7	Semi standard non polar	33892256
(5E)-5-[(3Ar,4S,5S,6aR)-5-hydroxy-4-[(E,3R)-3-hydroxyoct-1-enyl]-3,3a,4,5,6,6a-hexahydro-1H-pentalen-2-ylidene]pentanoic acid,1TBDMS,isomer #3	CCCCCC(O)C=CC1C(O)CC2CC(=CCCCC(=O)O[Si](C)(C)C(C)(C)C)CC21	3045.1	Standard non polar	33892256
(5E)-5-[(3Ar,4S,5S,6aR)-5-hydroxy-4-[(E,3R)-3-hydroxyoct-1-enyl]-3,3a,4,5,6,6a-hexahydro-1H-pentalen-2-ylidene]pentanoic acid,1TBDMS,isomer #3	CCCCCC(O)C=CC1C(O)CC2CC(=CCCCC(=O)O[Si](C)(C)C(C)(C)C)CC21	3830.5	Standard polar	33892256
(5E)-5-[(3Ar,4S,5S,6aR)-5-hydroxy-4-[(E,3R)-3-hydroxyoct-1-enyl]-3,3a,4,5,6,6a-hexahydro-1H-pentalen-2-ylidene]pentanoic acid,2TBDMS,isomer #3	CCCCCC(O)C=CC1C(O[Si](C)(C)C(C)(C)C)CC2CC(=CCCCC(=O)O[Si](C)(C)C(C)(C)C)CC21	3345.6	Semi standard non polar	33892256
(5E)-5-[(3Ar,4S,5S,6aR)-5-hydroxy-4-[(E,3R)-3-hydroxyoct-1-enyl]-3,3a,4,5,6,6a-hexahydro-1H-pentalen-2-ylidene]pentanoic acid,2TBDMS,isomer #3	CCCCCC(O)C=CC1C(O[Si](C)(C)C(C)(C)C)CC2CC(=CCCCC(=O)O[Si](C)(C)C(C)(C)C)CC21	3313.0	Standard non polar	33892256
(5E)-5-[(3Ar,4S,5S,6aR)-5-hydroxy-4-[(E,3R)-3-hydroxyoct-1-enyl]-3,3a,4,5,6,6a-hexahydro-1H-pentalen-2-ylidene]pentanoic acid,2TBDMS,isomer #3	CCCCCC(O)C=CC1C(O[Si](C)(C)C(C)(C)C)CC2CC(=CCCCC(=O)O[Si](C)(C)C(C)(C)C)CC21	3585.8	Standard polar	33892256
(5E)-5-[(3Ar,4S,5S,6aR)-5-hydroxy-4-[(E,3R)-3-hydroxyoct-1-enyl]-3,3a,4,5,6,6a-hexahydro-1H-pentalen-2-ylidene]pentanoic acid,3TBDMS,isomer #1	CCCCCC(C=CC1C(O[Si](C)(C)C(C)(C)C)CC2CC(=CCCCC(=O)O[Si](C)(C)C(C)(C)C)CC21)O[Si](C)(C)C(C)(C)C	3591.6	Semi standard non polar	33892256
(5E)-5-[(3Ar,4S,5S,6aR)-5-hydroxy-4-[(E,3R)-3-hydroxyoct-1-enyl]-3,3a,4,5,6,6a-hexahydro-1H-pentalen-2-ylidene]pentanoic acid,3TBDMS,isomer #1	CCCCCC(C=CC1C(O[Si](C)(C)C(C)(C)C)CC2CC(=CCCCC(=O)O[Si](C)(C)C(C)(C)C)CC21)O[Si](C)(C)C(C)(C)C	3520.1	Standard non polar	33892256
(5E)-5-[(3Ar,4S,5S,6aR)-5-hydroxy-4-[(E,3R)-3-hydroxyoct-1-enyl]-3,3a,4,5,6,6a-hexahydro-1H-pentalen-2-ylidene]pentanoic acid,3TBDMS,isomer #1	CCCCCC(C=CC1C(O[Si](C)(C)C(C)(C)C)CC2CC(=CCCCC(=O)O[Si](C)(C)C(C)(C)C)CC21)O[Si](C)(C)C(C)(C)C	3323.6	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - (5E)-5-[(3Ar,4S,5S,6aR)-5-hydroxy-4-[(E,3R)-3-hydroxyoct-1-enyl]-3,3a,4,5,6,6a-hexahydro-1H-pentalen-2-ylidene]pentanoic acid GC-MS (Non-derivatized) - 70eV, Positive	splash10-017i-3693000000-eb0985884860ffdcdb31	2021-09-23	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (5E)-5-[(3Ar,4S,5S,6aR)-5-hydroxy-4-[(E,3R)-3-hydroxyoct-1-enyl]-3,3a,4,5,6,6a-hexahydro-1H-pentalen-2-ylidene]pentanoic acid GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (5E)-5-[(3Ar,4S,5S,6aR)-5-hydroxy-4-[(E,3R)-3-hydroxyoct-1-enyl]-3,3a,4,5,6,6a-hexahydro-1H-pentalen-2-ylidene]pentanoic acid GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (5E)-5-[(3Ar,4S,5S,6aR)-5-hydroxy-4-[(E,3R)-3-hydroxyoct-1-enyl]-3,3a,4,5,6,6a-hexahydro-1H-pentalen-2-ylidene]pentanoic acid GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (5E)-5-[(3Ar,4S,5S,6aR)-5-hydroxy-4-[(E,3R)-3-hydroxyoct-1-enyl]-3,3a,4,5,6,6a-hexahydro-1H-pentalen-2-ylidene]pentanoic acid GC-MS (TMS_1_3) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (5E)-5-[(3Ar,4S,5S,6aR)-5-hydroxy-4-[(E,3R)-3-hydroxyoct-1-enyl]-3,3a,4,5,6,6a-hexahydro-1H-pentalen-2-ylidene]pentanoic acid GC-MS (TMS_2_1) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (5E)-5-[(3Ar,4S,5S,6aR)-5-hydroxy-4-[(E,3R)-3-hydroxyoct-1-enyl]-3,3a,4,5,6,6a-hexahydro-1H-pentalen-2-ylidene]pentanoic acid GC-MS (TMS_2_2) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (5E)-5-[(3Ar,4S,5S,6aR)-5-hydroxy-4-[(E,3R)-3-hydroxyoct-1-enyl]-3,3a,4,5,6,6a-hexahydro-1H-pentalen-2-ylidene]pentanoic acid GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (5E)-5-[(3Ar,4S,5S,6aR)-5-hydroxy-4-[(E,3R)-3-hydroxyoct-1-enyl]-3,3a,4,5,6,6a-hexahydro-1H-pentalen-2-ylidene]pentanoic acid GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (5E)-5-[(3Ar,4S,5S,6aR)-5-hydroxy-4-[(E,3R)-3-hydroxyoct-1-enyl]-3,3a,4,5,6,6a-hexahydro-1H-pentalen-2-ylidene]pentanoic acid GC-MS (TBDMS_2_1) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (5E)-5-[(3Ar,4S,5S,6aR)-5-hydroxy-4-[(E,3R)-3-hydroxyoct-1-enyl]-3,3a,4,5,6,6a-hexahydro-1H-pentalen-2-ylidene]pentanoic acid GC-MS (TBDMS_2_2) - 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 - (5E)-5-[(3Ar,4S,5S,6aR)-5-hydroxy-4-[(E,3R)-3-hydroxyoct-1-enyl]-3,3a,4,5,6,6a-hexahydro-1H-pentalen-2-ylidene]pentanoic acid 10V, Positive-QTOF	splash10-014i-0019000000-d3a614a306a4d0296f46	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (5E)-5-[(3Ar,4S,5S,6aR)-5-hydroxy-4-[(E,3R)-3-hydroxyoct-1-enyl]-3,3a,4,5,6,6a-hexahydro-1H-pentalen-2-ylidene]pentanoic acid 20V, Positive-QTOF	splash10-014i-2379000000-2c43e8cdcc411d672670	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (5E)-5-[(3Ar,4S,5S,6aR)-5-hydroxy-4-[(E,3R)-3-hydroxyoct-1-enyl]-3,3a,4,5,6,6a-hexahydro-1H-pentalen-2-ylidene]pentanoic acid 40V, Positive-QTOF	splash10-05tf-9710000000-de01b0f3e0f20be4b0e7	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (5E)-5-[(3Ar,4S,5S,6aR)-5-hydroxy-4-[(E,3R)-3-hydroxyoct-1-enyl]-3,3a,4,5,6,6a-hexahydro-1H-pentalen-2-ylidene]pentanoic acid 10V, Negative-QTOF	splash10-0002-0009000000-0643b1007effbe0de5d2	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (5E)-5-[(3Ar,4S,5S,6aR)-5-hydroxy-4-[(E,3R)-3-hydroxyoct-1-enyl]-3,3a,4,5,6,6a-hexahydro-1H-pentalen-2-ylidene]pentanoic acid 20V, Negative-QTOF	splash10-000t-0039000000-20eb404e8011c32ae05c	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (5E)-5-[(3Ar,4S,5S,6aR)-5-hydroxy-4-[(E,3R)-3-hydroxyoct-1-enyl]-3,3a,4,5,6,6a-hexahydro-1H-pentalen-2-ylidene]pentanoic acid 40V, Negative-QTOF	splash10-0032-2091000000-19b4c8dc3d65a7e74e18	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

2455

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

2552

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 (5E)-5-[(3Ar,4S,5S,6aR)-5-hydroxy-4-[(E,3R)-3-hydroxyoct-1-enyl]-3,3a,4,5,6,6a-hexahydro-1H-pentalen-2-ylidene]pentanoic acid (HMDB0247207)

MOL for HMDB0247207 ((5E)-5-[(3Ar,4S,5S,6aR)-5-hydroxy-4-[(E,3R)-3-hydroxyoct-1-enyl]-3,3a,4,5,6,6a-hexahydro-1H-pentalen-2-ylidene]pentanoic acid)

3D MOL for HMDB0247207 ((5E)-5-[(3Ar,4S,5S,6aR)-5-hydroxy-4-[(E,3R)-3-hydroxyoct-1-enyl]-3,3a,4,5,6,6a-hexahydro-1H-pentalen-2-ylidene]pentanoic acid)

3D SDF for HMDB0247207 ((5E)-5-[(3Ar,4S,5S,6aR)-5-hydroxy-4-[(E,3R)-3-hydroxyoct-1-enyl]-3,3a,4,5,6,6a-hexahydro-1H-pentalen-2-ylidene]pentanoic acid)

3D-SDF for HMDB0247207 ((5E)-5-[(3Ar,4S,5S,6aR)-5-hydroxy-4-[(E,3R)-3-hydroxyoct-1-enyl]-3,3a,4,5,6,6a-hexahydro-1H-pentalen-2-ylidene]pentanoic acid)

PDB for HMDB0247207 ((5E)-5-[(3Ar,4S,5S,6aR)-5-hydroxy-4-[(E,3R)-3-hydroxyoct-1-enyl]-3,3a,4,5,6,6a-hexahydro-1H-pentalen-2-ylidene]pentanoic acid)

3D PDB for HMDB0247207 ((5E)-5-[(3Ar,4S,5S,6aR)-5-hydroxy-4-[(E,3R)-3-hydroxyoct-1-enyl]-3,3a,4,5,6,6a-hexahydro-1H-pentalen-2-ylidene]pentanoic acid)

SMILES for HMDB0247207 ((5E)-5-[(3Ar,4S,5S,6aR)-5-hydroxy-4-[(E,3R)-3-hydroxyoct-1-enyl]-3,3a,4,5,6,6a-hexahydro-1H-pentalen-2-ylidene]pentanoic acid)

INCHI for HMDB0247207 ((5E)-5-[(3Ar,4S,5S,6aR)-5-hydroxy-4-[(E,3R)-3-hydroxyoct-1-enyl]-3,3a,4,5,6,6a-hexahydro-1H-pentalen-2-ylidene]pentanoic acid)

Structure for HMDB0247207 ((5E)-5-[(3Ar,4S,5S,6aR)-5-hydroxy-4-[(E,3R)-3-hydroxyoct-1-enyl]-3,3a,4,5,6,6a-hexahydro-1H-pentalen-2-ylidene]pentanoic acid)

3D Structure for HMDB0247207 ((5E)-5-[(3Ar,4S,5S,6aR)-5-hydroxy-4-[(E,3R)-3-hydroxyoct-1-enyl]-3,3a,4,5,6,6a-hexahydro-1H-pentalen-2-ylidene]pentanoic acid)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Derivatized

GC-MS Spectra

MS/MS Spectra