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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-11 17:28:18 UTC

Update Date

2021-09-26 23:12:49 UTC

HMDB ID

HMDB0256856

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Prostaglandin I3

Description

5-[5-hydroxy-4-(3-hydroxyocta-1,5-dien-1-yl)-hexahydro-2H-cyclopenta[b]furan-2-ylidene]pentanoic acid 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 very few articles have been published on 5-[5-hydroxy-4-(3-hydroxyocta-1,5-dien-1-yl)-hexahydro-2H-cyclopenta[b]furan-2-ylidene]pentanoic acid. This compound has been identified in human blood as reported by (PMID: 31557052 ). Prostaglandin i3 is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically Prostaglandin I3 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

HMDB0256856
     RDKit          3D
Prostaglandin I3
 55 56  0  0  0  0  0  0  0  0999 V2000
    8.7180   -0.3884   -0.1511 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8510   -1.1970    0.7868 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3970   -1.0301    0.4707 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0408   -0.2417   -0.5294 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6496    0.0011   -0.9359 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6205   -0.7291   -0.1317 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8416   -2.0956   -0.2560 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2735   -0.4005   -0.6323 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4498    0.3423    0.0891 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1016    0.6435   -0.4642 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1270    2.1421   -0.5124 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0912    2.8420   -0.3618 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0612    2.4864    0.6269 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2638    1.2389    1.4211 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5910    0.9828    1.7936 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2351    0.1412    0.8836 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4577   -0.3469    0.9703 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0085   -1.2142   -0.0527 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2754   -0.6774   -0.6869 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3753   -0.4822    0.3270 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5637    0.0387   -0.3732 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.6119    1.2320   -0.7329 O   0  0  0  0  0  0  0  0  0  0  0  0
   -9.6302   -0.7903   -0.6353 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2713   -0.1010   -0.2086 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9222    0.0935    0.4908 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5141    0.6860   -0.0610 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.7731   -0.5851    0.1552 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.5676   -0.7499   -1.1927 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.9717   -0.8098    1.8371 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.1573   -2.2600    0.7684 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6595   -1.5462    1.0563 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8189    0.2806   -1.1142 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4763   -0.1893   -2.0177 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4558    1.1044   -0.8097 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7145   -0.4925    0.9503 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3661   -2.6217    0.4218 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9974   -0.7966   -1.6134 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7842    0.7019    1.0505 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0291    0.2085   -1.4703 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6147    2.4558   -1.4585 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8530    3.7585   -0.0703 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0357    2.8511    0.2533 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5688    3.2840    1.2535 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6108    1.2583    2.3181 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0471   -0.0823    1.8326 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2902   -1.3311   -0.8862 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1676   -2.2329    0.3549 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0832    0.2387   -1.2420 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6202   -1.4496   -1.4052 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1048    0.2616    1.1030 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6490   -1.4286    0.8304 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.5733   -1.6274   -1.2059 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3969    0.5804   -1.0625 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3337   -1.1386   -0.6171 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6241   -0.8182    1.0068 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  3
  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
  4 32  1  0
  5 33  1  0
  5 34  1  0
  6 35  1  0
  7 36  1  0
  8 37  1  0
  9 38  1  0
 10 39  1  0
 11 40  1  0
 12 41  1  0
 13 42  1  0
 13 43  1  0
 14 44  1  0
 17 45  1  0
 18 46  1  0
 18 47  1  0
 19 48  1  0
 19 49  1  0
 20 50  1  0
 20 51  1  0
 23 52  1  0
 24 53  1  0
 24 54  1  0
 25 55  1  0
M  END


  Mrv1533004231522022D          

 25 26  0  0  0  0            999 V2000
  -11.9355    1.1325    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -11.1509    0.8775    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.5378    1.4296    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.7532    1.1746    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.1401    1.7267    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.3555    1.4717    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1839    0.6648    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7424    2.0238    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9577    1.7688    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3446    2.3209    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4309    3.1413    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1454    3.5538    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6772    3.4769    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1252    2.8638    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3182    2.6923    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2320    1.8718    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5175    1.4593    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8030    1.8718    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0886    1.4593    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3741    1.8718    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6596    1.4593    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0549    1.8718    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6596    0.6343    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9856    1.5362    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5377    2.1493    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  3  2  1  4  0  0  0
  3  4  2  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
  8  6  1  4  0  0  0
  8  9  2  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
 11 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  2  0  0  0  0
 17 18  1  4  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  2  0  0  0  0
 21 23  1  0  0  0  0
 16 24  1  0  0  0  0
 24 25  1  0  0  0  0
 10 25  1  0  0  0  0
 14 25  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0256856

> <DATABASE_NAME>
hmdb

> <SMILES>
CCC=CCC(O)C=CC1C(O)CC2OC(CC12)=CCCCC(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C20H30O5/c1-2-3-4-7-14(21)10-11-16-17-12-15(8-5-6-9-20(23)24)25-19(17)13-18(16)22/h3-4,8,10-11,14,16-19,21-22H,2,5-7,9,12-13H2,1H3,(H,23,24)

> <INCHI_KEY>
NCYSTSFUYSFMEO-UHFFFAOYSA-N

> <FORMULA>
C20H30O5

> <MOLECULAR_WEIGHT>
350.455

> <EXACT_MASS>
350.209324066

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
55

> <JCHEM_AVERAGE_POLARIZABILITY>
40.70354008043745

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
5-[5-hydroxy-4-(3-hydroxyocta-1,5-dien-1-yl)-hexahydro-2H-cyclopenta[b]furan-2-ylidene]pentanoic acid

> <ALOGPS_LOGP>
3.90

> <JCHEM_LOGP>
2.053782859666666

> <ALOGPS_LOGS>
-3.42

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
14.796423930214992

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.429290479601213

> <JCHEM_PKA_STRONGEST_BASIC>
-1.6649367505193062

> <JCHEM_POLAR_SURFACE_AREA>
86.99

> <JCHEM_REFRACTIVITY>
100.12349999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
9

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.34e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
5-[5-hydroxy-4-(3-hydroxyocta-1,5-dien-1-yl)-hexahydrocyclopenta[b]furan-2-ylidene]pentanoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0256856
     RDKit          3D
Prostaglandin I3
 55 56  0  0  0  0  0  0  0  0999 V2000
    8.7180   -0.3884   -0.1511 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8510   -1.1970    0.7868 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3970   -1.0301    0.4707 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0408   -0.2417   -0.5294 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6496    0.0011   -0.9359 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6205   -0.7291   -0.1317 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8416   -2.0956   -0.2560 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2735   -0.4005   -0.6323 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4498    0.3423    0.0891 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1016    0.6435   -0.4642 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1270    2.1421   -0.5124 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0912    2.8420   -0.3618 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0612    2.4864    0.6269 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2638    1.2389    1.4211 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5910    0.9828    1.7936 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2351    0.1412    0.8836 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4577   -0.3469    0.9703 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0085   -1.2142   -0.0527 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2754   -0.6774   -0.6869 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3753   -0.4822    0.3270 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5637    0.0387   -0.3732 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.6119    1.2320   -0.7329 O   0  0  0  0  0  0  0  0  0  0  0  0
   -9.6302   -0.7903   -0.6353 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2713   -0.1010   -0.2086 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9222    0.0935    0.4908 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5141    0.6860   -0.0610 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.7731   -0.5851    0.1552 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.5676   -0.7499   -1.1927 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.9717   -0.8098    1.8371 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.1573   -2.2600    0.7684 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6595   -1.5462    1.0563 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8189    0.2806   -1.1142 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4763   -0.1893   -2.0177 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4558    1.1044   -0.8097 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7145   -0.4925    0.9503 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3661   -2.6217    0.4218 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9974   -0.7966   -1.6134 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7842    0.7019    1.0505 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0291    0.2085   -1.4703 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6147    2.4558   -1.4585 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8530    3.7585   -0.0703 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0357    2.8511    0.2533 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5688    3.2840    1.2535 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6108    1.2583    2.3181 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0471   -0.0823    1.8326 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2902   -1.3311   -0.8862 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1676   -2.2329    0.3549 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0832    0.2387   -1.2420 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6202   -1.4496   -1.4052 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1048    0.2616    1.1030 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6490   -1.4286    0.8304 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.5733   -1.6274   -1.2059 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3969    0.5804   -1.0625 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3337   -1.1386   -0.6171 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6241   -0.8182    1.0068 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  3
  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
  4 32  1  0
  5 33  1  0
  5 34  1  0
  6 35  1  0
  7 36  1  0
  8 37  1  0
  9 38  1  0
 10 39  1  0
 11 40  1  0
 12 41  1  0
 13 42  1  0
 13 43  1  0
 14 44  1  0
 17 45  1  0
 18 46  1  0
 18 47  1  0
 19 48  1  0
 19 49  1  0
 20 50  1  0
 20 51  1  0
 23 52  1  0
 24 53  1  0
 24 54  1  0
 25 55  1  0
M  END

HEADER    PROTEIN                                 23-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-APR-15         0                                  
HETATM    1  C   UNK     0     -22.280   2.114   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0     -20.815   1.638   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0     -19.671   2.669   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0     -18.206   2.193   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0     -17.061   3.223   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0     -15.597   2.747   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0     -15.277   1.241   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0     -14.452   3.778   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0     -12.988   3.302   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0     -11.843   4.332   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0     -12.004   5.864   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0     -13.338   6.634   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0     -10.597   6.490   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -9.567   5.346   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      -8.061   5.026   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0      -7.900   3.494   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -6.566   2.724   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -5.232   3.494   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -3.899   2.724   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -2.565   3.494   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -1.231   2.724   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       0.102   3.494   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0      -1.231   1.184   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0      -9.307   2.868   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0     -10.337   4.012   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11   25                                                  
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14                                                       
CONECT   14   13   15   25                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17   24                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21                                                            
CONECT   24   16   25                                                       
CONECT   25   24   10   14                                                  
MASTER        0    0    0    0    0    0    0    0   25    0   52    0
END

COMPND    HMDB0256856
HETATM    1  C1  UNL     1       8.718  -0.388  -0.151  1.00  0.00           C  
HETATM    2  C2  UNL     1       7.851  -1.197   0.787  1.00  0.00           C  
HETATM    3  C3  UNL     1       6.397  -1.030   0.471  1.00  0.00           C  
HETATM    4  C4  UNL     1       6.041  -0.242  -0.529  1.00  0.00           C  
HETATM    5  C5  UNL     1       4.650   0.001  -0.936  1.00  0.00           C  
HETATM    6  C6  UNL     1       3.621  -0.729  -0.132  1.00  0.00           C  
HETATM    7  O1  UNL     1       3.842  -2.096  -0.256  1.00  0.00           O  
HETATM    8  C7  UNL     1       2.274  -0.400  -0.632  1.00  0.00           C  
HETATM    9  C8  UNL     1       1.450   0.342   0.089  1.00  0.00           C  
HETATM   10  C9  UNL     1       0.102   0.644  -0.464  1.00  0.00           C  
HETATM   11  C10 UNL     1      -0.127   2.142  -0.512  1.00  0.00           C  
HETATM   12  O2  UNL     1       1.091   2.842  -0.362  1.00  0.00           O  
HETATM   13  C11 UNL     1      -1.061   2.486   0.627  1.00  0.00           C  
HETATM   14  C12 UNL     1      -1.264   1.239   1.421  1.00  0.00           C  
HETATM   15  O3  UNL     1      -2.591   0.983   1.794  1.00  0.00           O  
HETATM   16  C13 UNL     1      -3.235   0.141   0.884  1.00  0.00           C  
HETATM   17  C14 UNL     1      -4.458  -0.347   0.970  1.00  0.00           C  
HETATM   18  C15 UNL     1      -5.009  -1.214  -0.053  1.00  0.00           C  
HETATM   19  C16 UNL     1      -6.275  -0.677  -0.687  1.00  0.00           C  
HETATM   20  C17 UNL     1      -7.375  -0.482   0.327  1.00  0.00           C  
HETATM   21  C18 UNL     1      -8.564   0.039  -0.373  1.00  0.00           C  
HETATM   22  O4  UNL     1      -8.612   1.232  -0.733  1.00  0.00           O  
HETATM   23  O5  UNL     1      -9.630  -0.790  -0.635  1.00  0.00           O  
HETATM   24  C19 UNL     1      -2.271  -0.101  -0.209  1.00  0.00           C  
HETATM   25  C20 UNL     1      -0.922   0.094   0.491  1.00  0.00           C  
HETATM   26  H1  UNL     1       8.514   0.686  -0.061  1.00  0.00           H  
HETATM   27  H2  UNL     1       9.773  -0.585   0.155  1.00  0.00           H  
HETATM   28  H3  UNL     1       8.568  -0.750  -1.193  1.00  0.00           H  
HETATM   29  H4  UNL     1       7.972  -0.810   1.837  1.00  0.00           H  
HETATM   30  H5  UNL     1       8.157  -2.260   0.768  1.00  0.00           H  
HETATM   31  H6  UNL     1       5.659  -1.546   1.056  1.00  0.00           H  
HETATM   32  H7  UNL     1       6.819   0.281  -1.114  1.00  0.00           H  
HETATM   33  H8  UNL     1       4.476  -0.189  -2.018  1.00  0.00           H  
HETATM   34  H9  UNL     1       4.456   1.104  -0.810  1.00  0.00           H  
HETATM   35  H10 UNL     1       3.715  -0.493   0.950  1.00  0.00           H  
HETATM   36  H11 UNL     1       3.366  -2.622   0.422  1.00  0.00           H  
HETATM   37  H12 UNL     1       1.997  -0.797  -1.613  1.00  0.00           H  
HETATM   38  H13 UNL     1       1.784   0.702   1.051  1.00  0.00           H  
HETATM   39  H14 UNL     1      -0.029   0.208  -1.470  1.00  0.00           H  
HETATM   40  H15 UNL     1      -0.615   2.456  -1.459  1.00  0.00           H  
HETATM   41  H16 UNL     1       0.853   3.759  -0.070  1.00  0.00           H  
HETATM   42  H17 UNL     1      -2.036   2.851   0.253  1.00  0.00           H  
HETATM   43  H18 UNL     1      -0.569   3.284   1.253  1.00  0.00           H  
HETATM   44  H19 UNL     1      -0.611   1.258   2.318  1.00  0.00           H  
HETATM   45  H20 UNL     1      -5.047  -0.082   1.833  1.00  0.00           H  
HETATM   46  H21 UNL     1      -4.290  -1.331  -0.886  1.00  0.00           H  
HETATM   47  H22 UNL     1      -5.168  -2.233   0.355  1.00  0.00           H  
HETATM   48  H23 UNL     1      -6.083   0.239  -1.242  1.00  0.00           H  
HETATM   49  H24 UNL     1      -6.620  -1.450  -1.405  1.00  0.00           H  
HETATM   50  H25 UNL     1      -7.105   0.262   1.103  1.00  0.00           H  
HETATM   51  H26 UNL     1      -7.649  -1.429   0.830  1.00  0.00           H  
HETATM   52  H27 UNL     1      -9.573  -1.627  -1.206  1.00  0.00           H  
HETATM   53  H28 UNL     1      -2.397   0.580  -1.062  1.00  0.00           H  
HETATM   54  H29 UNL     1      -2.334  -1.139  -0.617  1.00  0.00           H  
HETATM   55  H30 UNL     1      -0.624  -0.818   1.007  1.00  0.00           H  
CONECT    1    2   26   27   28
CONECT    2    3   29   30
CONECT    3    4    4   31
CONECT    4    5   32
CONECT    5    6   33   34
CONECT    6    7    8   35
CONECT    7   36
CONECT    8    9    9   37
CONECT    9   10   38
CONECT   10   11   25   39
CONECT   11   12   13   40
CONECT   12   41
CONECT   13   14   42   43
CONECT   14   15   25   44
CONECT   15   16
CONECT   16   17   17   24
CONECT   17   18   45
CONECT   18   19   46   47
CONECT   19   20   48   49
CONECT   20   21   50   51
CONECT   21   22   22   23
CONECT   23   52
CONECT   24   25   53   54
CONECT   25   55
END

HMDB0256856
     RDKit          3D
Prostaglandin I3
 55 56  0  0  0  0  0  0  0  0999 V2000
    8.7180   -0.3884   -0.1511 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8510   -1.1970    0.7868 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3970   -1.0301    0.4707 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0408   -0.2417   -0.5294 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6496    0.0011   -0.9359 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6205   -0.7291   -0.1317 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8416   -2.0956   -0.2560 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2735   -0.4005   -0.6323 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4498    0.3423    0.0891 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1016    0.6435   -0.4642 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1270    2.1421   -0.5124 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0912    2.8420   -0.3618 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0612    2.4864    0.6269 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2638    1.2389    1.4211 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5910    0.9828    1.7936 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2351    0.1412    0.8836 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4577   -0.3469    0.9703 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0085   -1.2142   -0.0527 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2754   -0.6774   -0.6869 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3753   -0.4822    0.3270 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5637    0.0387   -0.3732 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.6119    1.2320   -0.7329 O   0  0  0  0  0  0  0  0  0  0  0  0
   -9.6302   -0.7903   -0.6353 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2713   -0.1010   -0.2086 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9222    0.0935    0.4908 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5141    0.6860   -0.0610 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.7731   -0.5851    0.1552 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.5676   -0.7499   -1.1927 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.9717   -0.8098    1.8371 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.1573   -2.2600    0.7684 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6595   -1.5462    1.0563 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8189    0.2806   -1.1142 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4763   -0.1893   -2.0177 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4558    1.1044   -0.8097 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7145   -0.4925    0.9503 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3661   -2.6217    0.4218 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9974   -0.7966   -1.6134 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7842    0.7019    1.0505 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0291    0.2085   -1.4703 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6147    2.4558   -1.4585 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8530    3.7585   -0.0703 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0357    2.8511    0.2533 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5688    3.2840    1.2535 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6108    1.2583    2.3181 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0471   -0.0823    1.8326 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2902   -1.3311   -0.8862 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1676   -2.2329    0.3549 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0832    0.2387   -1.2420 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6202   -1.4496   -1.4052 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1048    0.2616    1.1030 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6490   -1.4286    0.8304 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.5733   -1.6274   -1.2059 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3969    0.5804   -1.0625 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3337   -1.1386   -0.6171 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6241   -0.8182    1.0068 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  3
  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
  4 32  1  0
  5 33  1  0
  5 34  1  0
  6 35  1  0
  7 36  1  0
  8 37  1  0
  9 38  1  0
 10 39  1  0
 11 40  1  0
 12 41  1  0
 13 42  1  0
 13 43  1  0
 14 44  1  0
 17 45  1  0
 18 46  1  0
 18 47  1  0
 19 48  1  0
 19 49  1  0
 20 50  1  0
 20 51  1  0
 23 52  1  0
 24 53  1  0
 24 54  1  0
 25 55  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
5-[5-Hydroxy-4-(3-hydroxyocta-1,5-dien-1-yl)-hexahydro-2H-cyclopenta[b]furan-2-ylidene]pentanoate	Generator

Chemical Formula

C₂₀H₃₀O₅

Average Molecular Weight

350.455

Monoisotopic Molecular Weight

350.209324066

IUPAC Name

5-[5-hydroxy-4-(3-hydroxyocta-1,5-dien-1-yl)-hexahydro-2H-cyclopenta[b]furan-2-ylidene]pentanoic acid

Traditional Name

5-[5-hydroxy-4-(3-hydroxyocta-1,5-dien-1-yl)-hexahydrocyclopenta[b]furan-2-ylidene]pentanoic acid

CAS Registry Number

Not Available

SMILES

CCC=CCC(O)C=CC1C(O)CC2OC(CC12)=CCCCC(O)=O

InChI Identifier

InChI=1S/C20H30O5/c1-2-3-4-7-14(21)10-11-16-17-12-15(8-5-6-9-20(23)24)25-19(17)13-18(16)22/h3-4,8,10-11,14,16-19,21-22H,2,5-7,9,12-13H2,1H3,(H,23,24)

InChI Key

NCYSTSFUYSFMEO-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
Fatty alcohol
Medium-chain hydroxy acid
Medium-chain fatty acid
Heterocyclic fatty acid
Hydroxy fatty acid
Cyclic alcohol
Tetrahydrofuran
Secondary alcohol
Organoheterocyclic compound
Monocarboxylic acid or derivatives
Oxacycle
Carboxylic acid
Carboxylic acid derivative
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Alcohol
Carbonyl group
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic 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	3.9	ALOGPS
logP	2.05	ChemAxon
logS	-3.4	ALOGPS
pKa (Strongest Acidic)	4.43	ChemAxon
pKa (Strongest Basic)	-1.7	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	86.99 Å²	ChemAxon
Rotatable Bond Count	9	ChemAxon
Refractivity	100.12 m³·mol⁻¹	ChemAxon
Polarizability	40.7 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]-	218.544	30932474
DeepCCS	[M+Na]+	194.109	30932474

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Prostaglandin I3	CCC=CCC(O)C=CC1C(O)CC2OC(CC12)=CCCCC(O)=O	4494.5	Standard polar	33892256
Prostaglandin I3	CCC=CCC(O)C=CC1C(O)CC2OC(CC12)=CCCCC(O)=O	2557.0	Standard non polar	33892256
Prostaglandin I3	CCC=CCC(O)C=CC1C(O)CC2OC(CC12)=CCCCC(O)=O	2882.4	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Prostaglandin I3 GC-MS (Non-derivatized) - 70eV, Positive	splash10-015c-9675000000-b232d0be1eb15a93b8e6	2021-09-23	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Prostaglandin I3 GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Prostaglandin I3 GC-MS (TMS_1_1) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Prostaglandin I3 GC-MS (TMS_1_2) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Prostaglandin I3 GC-MS (TMS_1_3) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Prostaglandin I3 GC-MS (TMS_2_1) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Prostaglandin I3 GC-MS (TMS_2_2) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Prostaglandin I3 GC-MS (TMS_2_3) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Prostaglandin I3 GC-MS (TMS_3_1) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Prostaglandin I3 GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Prostaglandin I3 GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Prostaglandin I3 GC-MS (TBDMS_1_3) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Prostaglandin I3 GC-MS (TBDMS_2_1) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Prostaglandin I3 GC-MS (TBDMS_2_2) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Prostaglandin I3 GC-MS (TBDMS_2_3) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Prostaglandin I3 GC-MS (TBDMS_3_1) - 70eV, Positive	Not Available	2021-11-05	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

21230790

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

53394238

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 Prostaglandin I3 (HMDB0256856)

MOL for HMDB0256856 (Prostaglandin I3)

3D MOL for HMDB0256856 (Prostaglandin I3)

3D SDF for HMDB0256856 (Prostaglandin I3)

3D-SDF for HMDB0256856 (Prostaglandin I3)

PDB for HMDB0256856 (Prostaglandin I3)

3D PDB for HMDB0256856 (Prostaglandin I3)

SMILES for HMDB0256856 (Prostaglandin I3)

INCHI for HMDB0256856 (Prostaglandin I3)

Structure for HMDB0256856 (Prostaglandin I3)

3D Structure for HMDB0256856 (Prostaglandin I3)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra