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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2017-11-01 19:34:38 UTC

Update Date

2022-03-07 03:18:13 UTC

HMDB ID

HMDB0240213

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Prostaglandin lactone-diol

Description

(3aR,4R,5R,6aS)-5-hydroxy-4-[(1E,3S)-3-hydroxyoct-1-en-1-yl]-hexahydro-2H-cyclopenta[b]furan-2-one belongs to the class of organic compounds known as fatty alcohols. These are aliphatic alcohols consisting of a chain of a least six carbon atoms. Based on a literature review very few articles have been published on (3aR,4R,5R,6aS)-5-hydroxy-4-[(1E,3S)-3-hydroxyoct-1-en-1-yl]-hexahydro-2H-cyclopenta[b]furan-2-one.

Structure

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

HMDB0240213
     RDKit          3D
Prostaglandin lactone-diol
 43 44  0  0  0  0  0  0  0  0999 V2000
    5.9947   -1.0266    0.0880 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5681    0.3606   -0.2934 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0815    0.5133    0.1014 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3019   -0.5128   -0.6412 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8315   -0.5605   -0.3742 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1378    0.6997   -0.7029 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.6353    1.7423    0.0620 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3318    0.6555   -0.4785 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0701   -0.4191   -0.4029 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5106   -0.5127   -0.1847 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.7615   -1.1691    1.1750 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.3567   -2.4929    1.1927 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2779   -1.0422    1.2492 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4639    0.4064    0.8508 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.5917    0.6236    0.0632 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2783    1.5730   -0.9294 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0182    2.5062   -1.3632 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8861    1.2105   -1.3316 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2497    0.7657   -0.0216 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.7125   -1.7789   -0.6881 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5693   -1.2754    1.0879 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1087   -1.0130    0.2495 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1734    1.1241    0.2159 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6456    0.4605   -1.3923 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9515    0.4142    1.1768 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8263    1.5246   -0.2861 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7051   -1.5172   -0.2997 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5188   -0.4946   -1.7415 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6974   -0.8168    0.7060 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4440   -1.4491   -0.9286 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3496    0.9900   -1.7684 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1014    2.5626    0.0036 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8358    1.6208   -0.3700 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5457   -1.3821   -0.5177 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0188   -1.1665   -0.9374 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3386   -0.5539    1.9638 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9649   -2.6538    2.0886 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6515   -1.2590    2.2576 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7170   -1.6801    0.4581 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4908    1.0548    1.7445 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9699    0.3281   -1.9950 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3401    2.0610   -1.7772 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6848    1.5788    0.4420 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  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 11 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  2  0
 16 18  1  0
 18 19  1  0
 19 10  1  0
 19 14  1  0
  1 20  1  0
  1 21  1  0
  1 22  1  0
  2 23  1  0
  2 24  1  0
  3 25  1  0
  3 26  1  0
  4 27  1  0
  4 28  1  0
  5 29  1  0
  5 30  1  0
  6 31  1  6
  7 32  1  0
  8 33  1  0
  9 34  1  0
 10 35  1  6
 11 36  1  1
 12 37  1  0
 13 38  1  0
 13 39  1  0
 14 40  1  1
 18 41  1  0
 18 42  1  0
 19 43  1  1
M  END


  Mrv1652311101723282D          

 21 22  0  0  0  0            999 V2000
   -3.1248    0.2785    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.4103   -0.1339    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6958    0.2785    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9814   -0.1339    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.2669    0.2785    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4475   -0.1339    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1620    0.2785    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8764   -0.1339    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5909    0.2785    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9814   -0.9589    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8699    1.0632    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.5373    1.5481    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.2047    1.0632    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9498    0.2786    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.2024    1.5480    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4572    2.3326    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2822    2.3327    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9722    3.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4347   -0.3887    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2047    2.0331    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2025    0.5782    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  4 10  1  6  0  0  0
  1  2  1  1  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
  1 11  1  0  0  0  0
  1 14  1  0  0  0  0
 15 16  1  0  0  0  0
 11 15  1  0  0  0  0
 16 17  1  0  0  0  0
 12 17  1  0  0  0  0
 16 18  2  0  0  0  0
 14 19  1  6  0  0  0
 11 21  1  1  0  0  0
 12 20  1  1  0  0  0
M  END
> <DATABASE_ID>
HMDB0240213

> <DATABASE_NAME>
hmdb

> <SMILES>
[H][C@]12C[C@@H](O)[C@H](\C=C\[C@@H](O)CCCCC)[C@@]1([H])CC(=O)O2

> <INCHI_IDENTIFIER>
InChI=1S/C15H24O4/c1-2-3-4-5-10(16)6-7-11-12-8-15(18)19-14(12)9-13(11)17/h6-7,10-14,16-17H,2-5,8-9H2,1H3/b7-6+/t10-,11+,12+,13+,14-/m0/s1

> <INCHI_KEY>
UMDQPEMZJHAFNL-FNLFQXNBSA-N

> <FORMULA>
C15H24O4

> <MOLECULAR_WEIGHT>
268.353

> <EXACT_MASS>
268.167459253

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
43

> <JCHEM_AVERAGE_POLARIZABILITY>
30.446159442691005

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(3aR,4R,5R,6aS)-5-hydroxy-4-[(1E,3S)-3-hydroxyoct-1-en-1-yl]-hexahydro-2H-cyclopenta[b]furan-2-one

> <ALOGPS_LOGP>
1.76

> <JCHEM_LOGP>
1.414603873666666

> <ALOGPS_LOGS>
-2.12

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
17.680578746973733

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.796069654479435

> <JCHEM_PKA_STRONGEST_BASIC>
-1.626313206494046

> <JCHEM_POLAR_SURFACE_AREA>
66.76

> <JCHEM_REFRACTIVITY>
72.8569

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.04e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(3aR,4R,5R,6aS)-5-hydroxy-4-[(1E,3S)-3-hydroxyoct-1-en-1-yl]-hexahydrocyclopenta[b]furan-2-one

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0240213
     RDKit          3D
Prostaglandin lactone-diol
 43 44  0  0  0  0  0  0  0  0999 V2000
    5.9947   -1.0266    0.0880 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5681    0.3606   -0.2934 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0815    0.5133    0.1014 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3019   -0.5128   -0.6412 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8315   -0.5605   -0.3742 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1378    0.6997   -0.7029 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.6353    1.7423    0.0620 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3318    0.6555   -0.4785 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0701   -0.4191   -0.4029 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5106   -0.5127   -0.1847 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.7615   -1.1691    1.1750 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.3567   -2.4929    1.1927 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2779   -1.0422    1.2492 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4639    0.4064    0.8508 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.5917    0.6236    0.0632 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2783    1.5730   -0.9294 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0182    2.5062   -1.3632 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8861    1.2105   -1.3316 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2497    0.7657   -0.0216 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.7125   -1.7789   -0.6881 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5693   -1.2754    1.0879 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1087   -1.0130    0.2495 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1734    1.1241    0.2159 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6456    0.4605   -1.3923 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9515    0.4142    1.1768 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8263    1.5246   -0.2861 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7051   -1.5172   -0.2997 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5188   -0.4946   -1.7415 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6974   -0.8168    0.7060 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4440   -1.4491   -0.9286 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3496    0.9900   -1.7684 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1014    2.5626    0.0036 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8358    1.6208   -0.3700 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5457   -1.3821   -0.5177 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0188   -1.1665   -0.9374 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3386   -0.5539    1.9638 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9649   -2.6538    2.0886 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6515   -1.2590    2.2576 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7170   -1.6801    0.4581 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4908    1.0548    1.7445 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9699    0.3281   -1.9950 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3401    2.0610   -1.7772 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6848    1.5788    0.4420 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  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 11 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  2  0
 16 18  1  0
 18 19  1  0
 19 10  1  0
 19 14  1  0
  1 20  1  0
  1 21  1  0
  1 22  1  0
  2 23  1  0
  2 24  1  0
  3 25  1  0
  3 26  1  0
  4 27  1  0
  4 28  1  0
  5 29  1  0
  5 30  1  0
  6 31  1  6
  7 32  1  0
  8 33  1  0
  9 34  1  0
 10 35  1  6
 11 36  1  1
 12 37  1  0
 13 38  1  0
 13 39  1  0
 14 40  1  1
 18 41  1  0
 18 42  1  0
 19 43  1  1
M  END

HEADER    PROTEIN                                 10-NOV-17   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   10-NOV-17         0                                  
HETATM    1  C   UNK     0      -5.833   0.520   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -4.499  -0.250   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -3.165   0.520   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -1.832  -0.250   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -0.498   0.520   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.835  -0.250   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.169   0.520   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       3.503  -0.250   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.836   0.520   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0      -1.832  -1.790   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0      -5.357   1.985   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -6.603   2.890   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -7.849   1.985   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -7.373   0.520   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -4.111   2.890   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -4.587   4.354   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      -6.127   4.354   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0      -3.681   5.600   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0      -8.278  -0.726   0.000  0.00  0.00           O+0
HETATM   20  H   UNK     0      -7.849   3.795   0.000  0.00  0.00           H+0
HETATM   21  H   UNK     0      -4.111   1.079   0.000  0.00  0.00           H+0
CONECT    1    2   11   14                                                  
CONECT    2    3    1                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5   10                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8                                                            
CONECT   10    4                                                            
CONECT   11   12    1   15   21                                             
CONECT   12   11   13   17   20                                             
CONECT   13   12   14                                                       
CONECT   14   13    1   19                                                  
CONECT   15   16   11                                                       
CONECT   16   15   17   18                                                  
CONECT   17   16   12                                                       
CONECT   18   16                                                            
CONECT   19   14                                                            
CONECT   20   12                                                            
CONECT   21   11                                                            
MASTER        0    0    0    0    0    0    0    0   21    0   44    0
END

COMPND    HMDB0240213
HETATM    1  C1  UNL     1       5.995  -1.027   0.088  1.00  0.00           C  
HETATM    2  C2  UNL     1       5.568   0.361  -0.293  1.00  0.00           C  
HETATM    3  C3  UNL     1       4.081   0.513   0.101  1.00  0.00           C  
HETATM    4  C4  UNL     1       3.302  -0.513  -0.641  1.00  0.00           C  
HETATM    5  C5  UNL     1       1.832  -0.560  -0.374  1.00  0.00           C  
HETATM    6  C6  UNL     1       1.138   0.700  -0.703  1.00  0.00           C  
HETATM    7  O1  UNL     1       1.635   1.742   0.062  1.00  0.00           O  
HETATM    8  C7  UNL     1      -0.332   0.655  -0.479  1.00  0.00           C  
HETATM    9  C8  UNL     1      -1.070  -0.419  -0.403  1.00  0.00           C  
HETATM   10  C9  UNL     1      -2.511  -0.513  -0.185  1.00  0.00           C  
HETATM   11  C10 UNL     1      -2.762  -1.169   1.175  1.00  0.00           C  
HETATM   12  O2  UNL     1      -2.357  -2.493   1.193  1.00  0.00           O  
HETATM   13  C11 UNL     1      -4.278  -1.042   1.249  1.00  0.00           C  
HETATM   14  C12 UNL     1      -4.464   0.406   0.851  1.00  0.00           C  
HETATM   15  O3  UNL     1      -5.592   0.624   0.063  1.00  0.00           O  
HETATM   16  C13 UNL     1      -5.278   1.573  -0.929  1.00  0.00           C  
HETATM   17  O4  UNL     1      -6.018   2.506  -1.363  1.00  0.00           O  
HETATM   18  C14 UNL     1      -3.886   1.211  -1.332  1.00  0.00           C  
HETATM   19  C15 UNL     1      -3.250   0.766  -0.022  1.00  0.00           C  
HETATM   20  H1  UNL     1       5.713  -1.779  -0.688  1.00  0.00           H  
HETATM   21  H2  UNL     1       5.569  -1.275   1.088  1.00  0.00           H  
HETATM   22  H3  UNL     1       7.109  -1.013   0.249  1.00  0.00           H  
HETATM   23  H4  UNL     1       6.173   1.124   0.216  1.00  0.00           H  
HETATM   24  H5  UNL     1       5.646   0.461  -1.392  1.00  0.00           H  
HETATM   25  H6  UNL     1       3.952   0.414   1.177  1.00  0.00           H  
HETATM   26  H7  UNL     1       3.826   1.525  -0.286  1.00  0.00           H  
HETATM   27  H8  UNL     1       3.705  -1.517  -0.300  1.00  0.00           H  
HETATM   28  H9  UNL     1       3.519  -0.495  -1.742  1.00  0.00           H  
HETATM   29  H10 UNL     1       1.697  -0.817   0.706  1.00  0.00           H  
HETATM   30  H11 UNL     1       1.444  -1.449  -0.929  1.00  0.00           H  
HETATM   31  H12 UNL     1       1.350   0.990  -1.768  1.00  0.00           H  
HETATM   32  H13 UNL     1       1.101   2.563   0.004  1.00  0.00           H  
HETATM   33  H14 UNL     1      -0.836   1.621  -0.370  1.00  0.00           H  
HETATM   34  H15 UNL     1      -0.546  -1.382  -0.518  1.00  0.00           H  
HETATM   35  H16 UNL     1      -3.019  -1.166  -0.937  1.00  0.00           H  
HETATM   36  H17 UNL     1      -2.339  -0.554   1.964  1.00  0.00           H  
HETATM   37  H18 UNL     1      -1.965  -2.654   2.089  1.00  0.00           H  
HETATM   38  H19 UNL     1      -4.651  -1.259   2.258  1.00  0.00           H  
HETATM   39  H20 UNL     1      -4.717  -1.680   0.458  1.00  0.00           H  
HETATM   40  H21 UNL     1      -4.491   1.055   1.744  1.00  0.00           H  
HETATM   41  H22 UNL     1      -3.970   0.328  -1.995  1.00  0.00           H  
HETATM   42  H23 UNL     1      -3.340   2.061  -1.777  1.00  0.00           H  
HETATM   43  H24 UNL     1      -2.685   1.579   0.442  1.00  0.00           H  
CONECT    1    2   20   21   22
CONECT    2    3   23   24
CONECT    3    4   25   26
CONECT    4    5   27   28
CONECT    5    6   29   30
CONECT    6    7    8   31
CONECT    7   32
CONECT    8    9    9   33
CONECT    9   10   34
CONECT   10   11   19   35
CONECT   11   12   13   36
CONECT   12   37
CONECT   13   14   38   39
CONECT   14   15   19   40
CONECT   15   16
CONECT   16   17   17   18
CONECT   18   19   41   42
CONECT   19   43
END

HMDB0240213
     RDKit          3D
Prostaglandin lactone-diol
 43 44  0  0  0  0  0  0  0  0999 V2000
    5.9947   -1.0266    0.0880 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5681    0.3606   -0.2934 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0815    0.5133    0.1014 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3019   -0.5128   -0.6412 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8315   -0.5605   -0.3742 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1378    0.6997   -0.7029 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.6353    1.7423    0.0620 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3318    0.6555   -0.4785 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0701   -0.4191   -0.4029 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5106   -0.5127   -0.1847 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.7615   -1.1691    1.1750 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.3567   -2.4929    1.1927 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2779   -1.0422    1.2492 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4639    0.4064    0.8508 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.5917    0.6236    0.0632 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2783    1.5730   -0.9294 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0182    2.5062   -1.3632 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8861    1.2105   -1.3316 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2497    0.7657   -0.0216 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.7125   -1.7789   -0.6881 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5693   -1.2754    1.0879 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1087   -1.0130    0.2495 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1734    1.1241    0.2159 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6456    0.4605   -1.3923 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9515    0.4142    1.1768 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8263    1.5246   -0.2861 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7051   -1.5172   -0.2997 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5188   -0.4946   -1.7415 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6974   -0.8168    0.7060 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4440   -1.4491   -0.9286 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3496    0.9900   -1.7684 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1014    2.5626    0.0036 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8358    1.6208   -0.3700 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5457   -1.3821   -0.5177 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0188   -1.1665   -0.9374 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3386   -0.5539    1.9638 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9649   -2.6538    2.0886 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6515   -1.2590    2.2576 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7170   -1.6801    0.4581 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4908    1.0548    1.7445 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9699    0.3281   -1.9950 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3401    2.0610   -1.7772 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6848    1.5788    0.4420 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  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 11 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  2  0
 16 18  1  0
 18 19  1  0
 19 10  1  0
 19 14  1  0
  1 20  1  0
  1 21  1  0
  1 22  1  0
  2 23  1  0
  2 24  1  0
  3 25  1  0
  3 26  1  0
  4 27  1  0
  4 28  1  0
  5 29  1  0
  5 30  1  0
  6 31  1  6
  7 32  1  0
  8 33  1  0
  9 34  1  0
 10 35  1  6
 11 36  1  1
 12 37  1  0
 13 38  1  0
 13 39  1  0
 14 40  1  1
 18 41  1  0
 18 42  1  0
 19 43  1  1
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
PG-lactone diol	HMDB

Chemical Formula

C₁₅H₂₄O₄

Average Molecular Weight

268.353

Monoisotopic Molecular Weight

268.167459253

IUPAC Name

(3aR,4R,5R,6aS)-5-hydroxy-4-[(1E,3S)-3-hydroxyoct-1-en-1-yl]-hexahydro-2H-cyclopenta[b]furan-2-one

Traditional Name

(3aR,4R,5R,6aS)-5-hydroxy-4-[(1E,3S)-3-hydroxyoct-1-en-1-yl]-hexahydrocyclopenta[b]furan-2-one

CAS Registry Number

26054-67-1

SMILES

[H][C@]12C[C@@H](O)[C@H](\C=C\[C@@H](O)CCCCC)[C@@]1([H])CC(=O)O2

InChI Identifier

InChI=1S/C15H24O4/c1-2-3-4-5-10(16)6-7-11-12-8-15(18)19-14(12)9-13(11)17/h6-7,10-14,16-17H,2-5,8-9H2,1H3/b7-6+/t10-,11+,12+,13+,14-/m0/s1

InChI Key

UMDQPEMZJHAFNL-FNLFQXNBSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as fatty alcohols. These are aliphatic alcohols consisting of a chain of a least six carbon atoms.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Fatty alcohols

Direct Parent

Fatty alcohols

Alternative Parents

Substituents

Fatty alcohol
Gamma butyrolactone
Cyclic alcohol
Tetrahydrofuran
Carboxylic acid ester
Lactone
Secondary alcohol
Carboxylic acid derivative
Oxacycle
Organoheterocyclic compound
Monocarboxylic acid or derivatives
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Carbonyl group
Alcohol
Organooxygen compound
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Not Available

Not Available

Not Available

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	1.76	ALOGPS
logP	1.41	ChemAxon
logS	-2.1	ALOGPS
pKa (Strongest Acidic)	14.8	ChemAxon
pKa (Strongest Basic)	-1.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	66.76 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	72.86 m³·mol⁻¹	ChemAxon
Polarizability	30.45 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
AllCCS	[M+H]+	167.802	31661259
AllCCS	[M-H]-	170.473	31661259
DeepCCS	[M-2H]-	202.783	30932474
DeepCCS	[M+Na]+	177.613	30932474
AllCCS	[M+H]+	167.8	32859911
AllCCS	[M+H-H2O]+	164.4	32859911
AllCCS	[M+NH4]+	170.9	32859911
AllCCS	[M+Na]+	171.8	32859911
AllCCS	[M-H]-	170.5	32859911
AllCCS	[M+Na-2H]-	170.7	32859911
AllCCS	[M+HCOO]-	171.1	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Prostaglandin lactone-diol	[H][C@]12C[C@@H](O)[C@H](\C=C\[C@@H](O)CCCCC)[C@@]1([H])CC(=O)O2	3706.2	Standard polar	33892256
Prostaglandin lactone-diol	[H][C@]12C[C@@H](O)[C@H](\C=C\[C@@H](O)CCCCC)[C@@]1([H])CC(=O)O2	2270.3	Standard non polar	33892256
Prostaglandin lactone-diol	[H][C@]12C[C@@H](O)[C@H](\C=C\[C@@H](O)CCCCC)[C@@]1([H])CC(=O)O2	2391.7	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Prostaglandin lactone-diol,1TMS,isomer #1	CCCCC[C@H](O)/C=C/[C@H]1[C@H](O[Si](C)(C)C)C[C@@H]2OC(=O)C[C@@H]21	2174.3	Semi standard non polar	33892256
Prostaglandin lactone-diol,1TMS,isomer #2	CCCCC[C@@H](/C=C/[C@H]1[C@H](O)C[C@@H]2OC(=O)C[C@@H]21)O[Si](C)(C)C	2213.0	Semi standard non polar	33892256
Prostaglandin lactone-diol,2TMS,isomer #1	CCCCC[C@@H](/C=C/[C@H]1[C@H](O[Si](C)(C)C)C[C@@H]2OC(=O)C[C@@H]21)O[Si](C)(C)C	2259.3	Semi standard non polar	33892256
Prostaglandin lactone-diol,1TBDMS,isomer #1	CCCCC[C@H](O)/C=C/[C@H]1[C@H](O[Si](C)(C)C(C)(C)C)C[C@@H]2OC(=O)C[C@@H]21	2389.6	Semi standard non polar	33892256
Prostaglandin lactone-diol,1TBDMS,isomer #2	CCCCC[C@@H](/C=C/[C@H]1[C@H](O)C[C@@H]2OC(=O)C[C@@H]21)O[Si](C)(C)C(C)(C)C	2431.7	Semi standard non polar	33892256
Prostaglandin lactone-diol,2TBDMS,isomer #1	CCCCC[C@@H](/C=C/[C@H]1[C@H](O[Si](C)(C)C(C)(C)C)C[C@@H]2OC(=O)C[C@@H]21)O[Si](C)(C)C(C)(C)C	2709.5	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 lactone-diol GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Prostaglandin lactone-diol 10V, Positive-QTOF	splash10-0uxr-0190000000-b9b50505121839eb8747	2019-02-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Prostaglandin lactone-diol 20V, Positive-QTOF	splash10-0ue9-3690000000-c4980bf5d161537479f9	2019-02-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Prostaglandin lactone-diol 40V, Positive-QTOF	splash10-0abc-9400000000-927a52e804d57d933ad6	2019-02-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Prostaglandin lactone-diol 10V, Negative-QTOF	splash10-014i-0090000000-043af6015d7221bb384a	2019-02-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Prostaglandin lactone-diol 20V, Negative-QTOF	splash10-01ba-1190000000-d41bb9728df4acc46b3f	2019-02-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Prostaglandin lactone-diol 40V, Negative-QTOF	splash10-006w-9840000000-fe0101a63c857b0c00c4	2019-02-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Prostaglandin lactone-diol 10V, Positive-QTOF	splash10-0gb9-0190000000-f953b4f96217e9ca6b85	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Prostaglandin lactone-diol 20V, Positive-QTOF	splash10-0f89-5970000000-2c6a11812be72c70aaf4	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Prostaglandin lactone-diol 40V, Positive-QTOF	splash10-0abj-9740000000-d39e906984edf5117386	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Prostaglandin lactone-diol 10V, Negative-QTOF	splash10-014i-0090000000-fc6ce45c3fedb72cc592	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Prostaglandin lactone-diol 20V, Negative-QTOF	splash10-014j-0290000000-be6c0a11c33a8e6f8f31	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Prostaglandin lactone-diol 40V, Negative-QTOF	splash10-00kn-9750000000-c1895bd2acd57febb6f1	2021-09-24	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

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

24534114

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

Not Available

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

Not Available

Showing metabocard for Prostaglandin lactone-diol (HMDB0240213)

MOL for HMDB0240213 (Prostaglandin lactone-diol)

3D MOL for HMDB0240213 (Prostaglandin lactone-diol)

3D SDF for HMDB0240213 (Prostaglandin lactone-diol)

3D-SDF for HMDB0240213 (Prostaglandin lactone-diol)

PDB for HMDB0240213 (Prostaglandin lactone-diol)

3D PDB for HMDB0240213 (Prostaglandin lactone-diol)

SMILES for HMDB0240213 (Prostaglandin lactone-diol)

INCHI for HMDB0240213 (Prostaglandin lactone-diol)

Structure for HMDB0240213 (Prostaglandin lactone-diol)

3D Structure for HMDB0240213 (Prostaglandin lactone-diol)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra