Jump To Section:

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

Record Information

Version

5.0

Status

Detected and Quantified

Creation Date

2006-08-13 14:58:41 UTC

Update Date

2022-03-07 02:49:20 UTC

HMDB ID

HMDB0004236

Secondary Accession Numbers

HMDB04236

Metabolite Identification

Common Name

Prostaglandin B2

Description

Prostaglandin B2 (PGB2) is a prostanoid. Prostanoids is a term that collectively describes prostaglandins, prostacyclines and thromboxanes. Prostanoids are a subclass of the lipid mediator group known as eicosanoids. They derive from C-20 polyunsaturated fatty acids, mainly dihomo-gamma-linoleic (20:3n-6), arachidonic (20:4n-6), and eicosapentaenoic (20:5n-3) acids, through the action of cyclooxygenases-1 and -2 (COX-1 and COX-2). The reaction product of COX is the unstable endoperoxide prostaglandin H (PGH) that is further transformed into the individual prostanoids by a series of specific prostanoid synthases. Prostanoids are local-acting mediators formed and inactivated within the same or neighbouring cells prior to their release into circulation as inactive metabolites (15-keto- and 13,14-dihydroketo metabolites). Non-enzymatic peroxidation of arachidonic acid and other fatty acids in vivo can result in prostaglandin-like substances isomeric to the COX-derived prostaglandins that are termed isoprostanes. Prostanoids take part in many physiological and pathophysiological processes in practically every organ, tissue and cell, including the vascular, renal, gastrointestinal and reproductive systems. Their activities are mediated through prostanoid-specific receptors and intracellular signalling pathways, whilst their biosynthesis and action are blocked by nonsteroidal antiinflammatory drugs (NSAID). Isoprostanes are considered to be reliable markers of oxidant stress status and have been linked to inflammation, ischaemia-reperfusion, diabetes, cardiovascular disease, reproductive disorders and diabetes. (PMID: 16986207 ). Prostaglandins are eicosanoids. The eicosanoids consist of the prostaglandins (PGs), thromboxanes (TXs), leukotrienes (LTs), and lipoxins (LXs). The PGs and TXs are collectively identified as prostanoids. Prostaglandins were originally shown to be synthesized in the prostate gland, thromboxanes from platelets (thrombocytes), and leukotrienes from leukocytes, hence the derivation of their names. All mammalian cells except erythrocytes synthesize eicosanoids. These molecules are extremely potent, able to cause profound physiological effects at very dilute concentrations. All eicosanoids function locally at the site of synthesis, through receptor-mediated G-protein linked signalling pathways.

Structure

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

HMDB0004236
     RDKit          3D
Prostaglandin B2
 54 54  0  0  0  0  0  0  0  0999 V2000
    7.6206    0.3934   -1.3512 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3066   -0.0353   -2.0137 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5137   -0.8667   -1.0078 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2046   -0.0889    0.2260 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3965    1.1412    0.0090 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0537    0.8988   -0.6015 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.0789    0.3016   -1.8367 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1751    0.1977    0.3671 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8845    0.0528    0.2146 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0181   -0.6442    1.1801 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2676   -0.8491    1.1358 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1530   -0.3747    0.0065 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1380    0.5322    0.5951 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4246    0.3672    0.5688 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0641   -0.7920   -0.0790 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9782   -0.2441   -1.1882 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0397    0.6695   -0.6167 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9194    1.1760   -1.7302 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7140    0.8293   -2.9151 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.9646    2.0355   -1.4220 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7082   -1.5911    2.3198 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7492   -2.2482    2.4504 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6121   -1.3670    3.3209 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5876   -1.2543    2.4194 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8163   -0.3125   -0.5104 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5583    1.4443   -1.0052 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.4543    0.2850   -2.0594 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7260    0.8356   -2.3425 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5426   -0.7004   -2.8569 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2270   -1.6870   -0.6984 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6667   -1.3726   -1.4716 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7721   -0.7862    0.9702 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1864    0.2353    0.6656 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2197    1.6048    1.0110 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0123    1.8687   -0.5502 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5837    1.9156   -0.7486 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9879    0.9397   -2.5664 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6144   -0.2293    1.2670 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4403    0.4686   -0.6664 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5805   -1.2402   -0.5220 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5168    0.1348   -0.7643 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7246    1.4298    1.1013 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1029    1.1280    1.0604 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7740   -1.3062    0.6320 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4049   -1.4916   -0.5716 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4750   -1.0605   -1.7410 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3850    0.3472   -1.9125 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6702    0.1550    0.1365 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5840    1.6165   -0.2015 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.8032    2.9841   -1.1801 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5390   -2.2074    4.0392 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7630   -0.3925    3.8349 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0358   -2.2491    2.2211 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3719   -0.5970    2.8746 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  2  0
 11 12  1  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  2  0
 18 20  1  0
 11 21  1  0
 21 22  2  0
 21 23  1  0
 23 24  1  0
 24 10  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
  2 28  1  0
  2 29  1  0
  3 30  1  0
  3 31  1  0
  4 32  1  0
  4 33  1  0
  5 34  1  0
  5 35  1  0
  6 36  1  6
  7 37  1  0
  8 38  1  0
  9 39  1  0
 12 40  1  0
 12 41  1  0
 13 42  1  0
 14 43  1  0
 15 44  1  0
 15 45  1  0
 16 46  1  0
 16 47  1  0
 17 48  1  0
 17 49  1  0
 20 50  1  0
 23 51  1  0
 23 52  1  0
 24 53  1  0
 24 54  1  0
M  END


  Mrv0541 02231219542D          

 24 24  0  0  1  0            999 V2000
   23.9093  -11.5651    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.0119  -15.9771    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.9757  -11.6364    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.5341  -12.9954    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   24.5767  -14.5251    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.9093  -14.0401    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.2419  -14.5251    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.3218  -15.3097    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.3382  -11.5651    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.3382  -10.7401    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.4968  -15.3097    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.6238  -11.9776    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   22.4572  -14.2701    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.0528  -10.3276    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.9093  -13.2151    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.6238  -12.8026    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.0528   -9.5026    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.8442  -14.8222    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.0595  -14.5672    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.7672   -9.0901    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.8880  -13.7602    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.1033  -13.5053    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.9318  -12.6983    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.1472  -12.4433    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 12  1  1  6  0  0  0
  2 11  2  0  0  0  0
  3 24  1  0  0  0  0
  4 24  2  0  0  0  0
  5  6  1  0  0  0  0
  5  8  1  0  0  0  0
  6  7  2  0  0  0  0
  6 15  1  0  0  0  0
  7 11  1  0  0  0  0
  7 13  1  0  0  0  0
  8 11  1  0  0  0  0
  9 10  1  0  0  0  0
  9 12  1  0  0  0  0
 10 14  1  0  0  0  0
 12 16  1  0  0  0  0
 13 18  1  0  0  0  0
 14 17  1  0  0  0  0
 15 16  2  0  0  0  0
 17 20  1  0  0  0  0
 18 19  2  0  0  0  0
 19 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0004236

> <DATABASE_NAME>
hmdb

> <SMILES>
CCCCC[C@@H](O)\C=C\C1=C(C\C=C/CCCC(O)=O)C(=O)CC1

> <INCHI_IDENTIFIER>
InChI=1S/C20H30O4/c1-2-3-6-9-17(21)14-12-16-13-15-19(22)18(16)10-7-4-5-8-11-20(23)24/h4,7,12,14,17,21H,2-3,5-6,8-11,13,15H2,1H3,(H,23,24)/b7-4-,14-12+/t17-/m1/s1

> <INCHI_KEY>
PRFXRIUZNKLRHM-RYPCXPIFSA-N

> <FORMULA>
C20H30O4

> <MOLECULAR_WEIGHT>
334.4498

> <EXACT_MASS>
334.214409448

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
39.63533661958893

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(5Z)-7-{2-[(1E,3R)-3-hydroxyoct-1-en-1-yl]-5-oxocyclopent-1-en-1-yl}hept-5-enoic acid

> <ALOGPS_LOGP>
4.07

> <JCHEM_LOGP>
4.18485735

> <ALOGPS_LOGS>
-4.05

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
17.769121310332174

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.25375476006069

> <JCHEM_PKA_STRONGEST_BASIC>
-1.587391578492345

> <JCHEM_POLAR_SURFACE_AREA>
74.6

> <JCHEM_REFRACTIVITY>
98.6059

> <JCHEM_ROTATABLE_BOND_COUNT>
12

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.99e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(5Z)-7-{2-[(1E,3R)-3-hydroxyoct-1-en-1-yl]-5-oxocyclopent-1-en-1-yl}hept-5-enoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0004236
     RDKit          3D
Prostaglandin B2
 54 54  0  0  0  0  0  0  0  0999 V2000
    7.6206    0.3934   -1.3512 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3066   -0.0353   -2.0137 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5137   -0.8667   -1.0078 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2046   -0.0889    0.2260 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3965    1.1412    0.0090 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0537    0.8988   -0.6015 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.0789    0.3016   -1.8367 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1751    0.1977    0.3671 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8845    0.0528    0.2146 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0181   -0.6442    1.1801 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2676   -0.8491    1.1358 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1530   -0.3747    0.0065 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1380    0.5322    0.5951 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4246    0.3672    0.5688 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0641   -0.7920   -0.0790 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9782   -0.2441   -1.1882 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0397    0.6695   -0.6167 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9194    1.1760   -1.7302 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7140    0.8293   -2.9151 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.9646    2.0355   -1.4220 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7082   -1.5911    2.3198 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7492   -2.2482    2.4504 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6121   -1.3670    3.3209 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5876   -1.2543    2.4194 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8163   -0.3125   -0.5104 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5583    1.4443   -1.0052 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.4543    0.2850   -2.0594 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7260    0.8356   -2.3425 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5426   -0.7004   -2.8569 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2270   -1.6870   -0.6984 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6667   -1.3726   -1.4716 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7721   -0.7862    0.9702 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1864    0.2353    0.6656 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2197    1.6048    1.0110 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0123    1.8687   -0.5502 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5837    1.9156   -0.7486 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9879    0.9397   -2.5664 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6144   -0.2293    1.2670 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4403    0.4686   -0.6664 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5805   -1.2402   -0.5220 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5168    0.1348   -0.7643 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7246    1.4298    1.1013 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1029    1.1280    1.0604 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7740   -1.3062    0.6320 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4049   -1.4916   -0.5716 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4750   -1.0605   -1.7410 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3850    0.3472   -1.9125 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6702    0.1550    0.1365 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5840    1.6165   -0.2015 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.8032    2.9841   -1.1801 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5390   -2.2074    4.0392 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7630   -0.3925    3.8349 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0358   -2.2491    2.2211 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3719   -0.5970    2.8746 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  2  0
 11 12  1  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  2  0
 18 20  1  0
 11 21  1  0
 21 22  2  0
 21 23  1  0
 23 24  1  0
 24 10  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
  2 28  1  0
  2 29  1  0
  3 30  1  0
  3 31  1  0
  4 32  1  0
  4 33  1  0
  5 34  1  0
  5 35  1  0
  6 36  1  6
  7 37  1  0
  8 38  1  0
  9 39  1  0
 12 40  1  0
 12 41  1  0
 13 42  1  0
 14 43  1  0
 15 44  1  0
 15 45  1  0
 16 46  1  0
 16 47  1  0
 17 48  1  0
 17 49  1  0
 20 50  1  0
 23 51  1  0
 23 52  1  0
 24 53  1  0
 24 54  1  0
M  END

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  O   UNK     0      44.631 -21.588   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0      42.956 -29.824   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0      35.421 -21.721   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0      34.597 -24.258   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0      45.877 -27.114   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      44.631 -26.208   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      43.385 -27.114   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      45.401 -28.578   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      47.298 -21.588   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      47.298 -20.048   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      43.861 -28.578   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      45.964 -22.358   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      41.920 -26.638   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      48.632 -19.278   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      44.631 -24.668   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      45.964 -23.898   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      48.632 -17.738   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      40.776 -27.668   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      39.311 -27.192   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      49.965 -16.968   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      38.991 -25.686   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      37.526 -25.210   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      37.206 -23.703   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      35.741 -23.227   0.000  0.00  0.00           C+0
CONECT    1   12                                                            
CONECT    2   11                                                            
CONECT    3   24                                                            
CONECT    4   24                                                            
CONECT    5    6    8                                                       
CONECT    6    5    7   15                                                  
CONECT    7    6   11   13                                                  
CONECT    8    5   11                                                       
CONECT    9   10   12                                                       
CONECT   10    9   14                                                       
CONECT   11    2    7    8                                                  
CONECT   12    1    9   16                                                  
CONECT   13    7   18                                                       
CONECT   14   10   17                                                       
CONECT   15    6   16                                                       
CONECT   16   12   15                                                       
CONECT   17   14   20                                                       
CONECT   18   13   19                                                       
CONECT   19   18   21                                                       
CONECT   20   17                                                            
CONECT   21   19   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   24                                                       
CONECT   24    3    4   23                                                  
MASTER        0    0    0    0    0    0    0    0   24    0   48    0
END

COMPND    HMDB0004236
HETATM    1  C1  UNL     1       7.621   0.393  -1.351  1.00  0.00           C  
HETATM    2  C2  UNL     1       6.307  -0.035  -2.014  1.00  0.00           C  
HETATM    3  C3  UNL     1       5.514  -0.867  -1.008  1.00  0.00           C  
HETATM    4  C4  UNL     1       5.205  -0.089   0.226  1.00  0.00           C  
HETATM    5  C5  UNL     1       4.396   1.141   0.009  1.00  0.00           C  
HETATM    6  C6  UNL     1       3.054   0.899  -0.602  1.00  0.00           C  
HETATM    7  O1  UNL     1       3.079   0.302  -1.837  1.00  0.00           O  
HETATM    8  C7  UNL     1       2.175   0.198   0.367  1.00  0.00           C  
HETATM    9  C8  UNL     1       0.885   0.053   0.215  1.00  0.00           C  
HETATM   10  C9  UNL     1       0.018  -0.644   1.180  1.00  0.00           C  
HETATM   11  C10 UNL     1      -1.268  -0.849   1.136  1.00  0.00           C  
HETATM   12  C11 UNL     1      -2.153  -0.375   0.006  1.00  0.00           C  
HETATM   13  C12 UNL     1      -3.138   0.532   0.595  1.00  0.00           C  
HETATM   14  C13 UNL     1      -4.425   0.367   0.569  1.00  0.00           C  
HETATM   15  C14 UNL     1      -5.064  -0.792  -0.079  1.00  0.00           C  
HETATM   16  C15 UNL     1      -5.978  -0.244  -1.188  1.00  0.00           C  
HETATM   17  C16 UNL     1      -7.040   0.670  -0.617  1.00  0.00           C  
HETATM   18  C17 UNL     1      -7.919   1.176  -1.730  1.00  0.00           C  
HETATM   19  O2  UNL     1      -7.714   0.829  -2.915  1.00  0.00           O  
HETATM   20  O3  UNL     1      -8.965   2.035  -1.422  1.00  0.00           O  
HETATM   21  C18 UNL     1      -1.708  -1.591   2.320  1.00  0.00           C  
HETATM   22  O4  UNL     1      -2.749  -2.248   2.450  1.00  0.00           O  
HETATM   23  C19 UNL     1      -0.612  -1.367   3.321  1.00  0.00           C  
HETATM   24  C20 UNL     1       0.588  -1.254   2.419  1.00  0.00           C  
HETATM   25  H1  UNL     1       7.816  -0.312  -0.510  1.00  0.00           H  
HETATM   26  H2  UNL     1       7.558   1.444  -1.005  1.00  0.00           H  
HETATM   27  H3  UNL     1       8.454   0.285  -2.059  1.00  0.00           H  
HETATM   28  H4  UNL     1       5.726   0.836  -2.342  1.00  0.00           H  
HETATM   29  H5  UNL     1       6.543  -0.700  -2.857  1.00  0.00           H  
HETATM   30  H6  UNL     1       6.227  -1.687  -0.698  1.00  0.00           H  
HETATM   31  H7  UNL     1       4.667  -1.373  -1.472  1.00  0.00           H  
HETATM   32  H8  UNL     1       4.772  -0.786   0.970  1.00  0.00           H  
HETATM   33  H9  UNL     1       6.186   0.235   0.666  1.00  0.00           H  
HETATM   34  H10 UNL     1       4.220   1.605   1.011  1.00  0.00           H  
HETATM   35  H11 UNL     1       5.012   1.869  -0.550  1.00  0.00           H  
HETATM   36  H12 UNL     1       2.584   1.916  -0.749  1.00  0.00           H  
HETATM   37  H13 UNL     1       2.988   0.940  -2.566  1.00  0.00           H  
HETATM   38  H14 UNL     1       2.614  -0.229   1.267  1.00  0.00           H  
HETATM   39  H15 UNL     1       0.440   0.469  -0.666  1.00  0.00           H  
HETATM   40  H16 UNL     1      -2.581  -1.240  -0.522  1.00  0.00           H  
HETATM   41  H17 UNL     1      -1.517   0.135  -0.764  1.00  0.00           H  
HETATM   42  H18 UNL     1      -2.725   1.430   1.101  1.00  0.00           H  
HETATM   43  H19 UNL     1      -5.103   1.128   1.060  1.00  0.00           H  
HETATM   44  H20 UNL     1      -5.774  -1.306   0.632  1.00  0.00           H  
HETATM   45  H21 UNL     1      -4.405  -1.492  -0.572  1.00  0.00           H  
HETATM   46  H22 UNL     1      -6.475  -1.060  -1.741  1.00  0.00           H  
HETATM   47  H23 UNL     1      -5.385   0.347  -1.912  1.00  0.00           H  
HETATM   48  H24 UNL     1      -7.670   0.155   0.137  1.00  0.00           H  
HETATM   49  H25 UNL     1      -6.584   1.617  -0.202  1.00  0.00           H  
HETATM   50  H26 UNL     1      -8.803   2.984  -1.180  1.00  0.00           H  
HETATM   51  H27 UNL     1      -0.539  -2.207   4.039  1.00  0.00           H  
HETATM   52  H28 UNL     1      -0.763  -0.393   3.835  1.00  0.00           H  
HETATM   53  H29 UNL     1       1.036  -2.249   2.221  1.00  0.00           H  
HETATM   54  H30 UNL     1       1.372  -0.597   2.875  1.00  0.00           H  
CONECT    1    2   25   26   27
CONECT    2    3   28   29
CONECT    3    4   30   31
CONECT    4    5   32   33
CONECT    5    6   34   35
CONECT    6    7    8   36
CONECT    7   37
CONECT    8    9    9   38
CONECT    9   10   39
CONECT   10   11   11   24
CONECT   11   12   21
CONECT   12   13   40   41
CONECT   13   14   14   42
CONECT   14   15   43
CONECT   15   16   44   45
CONECT   16   17   46   47
CONECT   17   18   48   49
CONECT   18   19   19   20
CONECT   20   50
CONECT   21   22   22   23
CONECT   23   24   51   52
CONECT   24   53   54
END

HMDB0004236
     RDKit          3D
Prostaglandin B2
 54 54  0  0  0  0  0  0  0  0999 V2000
    7.6206    0.3934   -1.3512 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3066   -0.0353   -2.0137 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5137   -0.8667   -1.0078 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2046   -0.0889    0.2260 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3965    1.1412    0.0090 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0537    0.8988   -0.6015 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.0789    0.3016   -1.8367 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1751    0.1977    0.3671 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8845    0.0528    0.2146 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0181   -0.6442    1.1801 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2676   -0.8491    1.1358 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1530   -0.3747    0.0065 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1380    0.5322    0.5951 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4246    0.3672    0.5688 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0641   -0.7920   -0.0790 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9782   -0.2441   -1.1882 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0397    0.6695   -0.6167 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9194    1.1760   -1.7302 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7140    0.8293   -2.9151 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.9646    2.0355   -1.4220 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7082   -1.5911    2.3198 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7492   -2.2482    2.4504 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6121   -1.3670    3.3209 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5876   -1.2543    2.4194 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8163   -0.3125   -0.5104 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5583    1.4443   -1.0052 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.4543    0.2850   -2.0594 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7260    0.8356   -2.3425 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5426   -0.7004   -2.8569 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2270   -1.6870   -0.6984 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6667   -1.3726   -1.4716 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7721   -0.7862    0.9702 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1864    0.2353    0.6656 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2197    1.6048    1.0110 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0123    1.8687   -0.5502 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5837    1.9156   -0.7486 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9879    0.9397   -2.5664 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6144   -0.2293    1.2670 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4403    0.4686   -0.6664 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5805   -1.2402   -0.5220 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5168    0.1348   -0.7643 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7246    1.4298    1.1013 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1029    1.1280    1.0604 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7740   -1.3062    0.6320 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4049   -1.4916   -0.5716 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4750   -1.0605   -1.7410 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3850    0.3472   -1.9125 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6702    0.1550    0.1365 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5840    1.6165   -0.2015 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.8032    2.9841   -1.1801 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5390   -2.2074    4.0392 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7630   -0.3925    3.8349 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0358   -2.2491    2.2211 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3719   -0.5970    2.8746 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  2  0
 11 12  1  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  2  0
 18 20  1  0
 11 21  1  0
 21 22  2  0
 21 23  1  0
 23 24  1  0
 24 10  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
  2 28  1  0
  2 29  1  0
  3 30  1  0
  3 31  1  0
  4 32  1  0
  4 33  1  0
  5 34  1  0
  5 35  1  0
  6 36  1  6
  7 37  1  0
  8 38  1  0
  9 39  1  0
 12 40  1  0
 12 41  1  0
 13 42  1  0
 14 43  1  0
 15 44  1  0
 15 45  1  0
 16 46  1  0
 16 47  1  0
 17 48  1  0
 17 49  1  0
 20 50  1  0
 23 51  1  0
 23 52  1  0
 24 53  1  0
 24 54  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
PGB2	HMDB

Chemical Formula

C₂₀H₃₀O₄

Average Molecular Weight

334.4498

Monoisotopic Molecular Weight

334.214409448

IUPAC Name

(5Z)-7-{2-[(1E,3R)-3-hydroxyoct-1-en-1-yl]-5-oxocyclopent-1-en-1-yl}hept-5-enoic acid

Traditional Name

(5Z)-7-{2-[(1E,3R)-3-hydroxyoct-1-en-1-yl]-5-oxocyclopent-1-en-1-yl}hept-5-enoic acid

CAS Registry Number

13367-85-6

SMILES

CCCCC[C@@H](O)\C=C\C1=C(C\C=C/CCCC(O)=O)C(=O)CC1

InChI Identifier

InChI=1S/C20H30O4/c1-2-3-6-9-17(21)14-12-16-13-15-19(22)18(16)10-7-4-5-8-11-20(23)24/h4,7,12,14,17,21H,2-3,5-6,8-11,13,15H2,1H3,(H,23,24)/b7-4-,14-12+/t17-/m1/s1

InChI Key

PRFXRIUZNKLRHM-RYPCXPIFSA-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
Long-chain fatty acid
Hydroxy fatty acid
Fatty acid
Unsaturated fatty acid
Ketone
Cyclic ketone
Secondary alcohol
Carboxylic acid derivative
Carboxylic acid
Monocarboxylic acid or derivatives
Organic oxide
Organic oxygen compound
Alcohol
Hydrocarbon derivative
Carbonyl group
Organooxygen compound
Aliphatic homomonocyclic compound

Molecular Framework

Aliphatic homomonocyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 18953024)
Cerebrospinal Fluid (CSF) (PMID: 3791712)

Cellular substructure

Extracellular (HMDB: HMDB0004236)
Membrane (HMDB: HMDB0004236)

Source

Exogenous

Exogenous (HMDB: HMDB0004236)

Food

Animal origin

Poultry

Pheasant (FooDB: FOOD00430)
Squab (FooDB: FOOD00481)
Turkey (FooDB: FOOD00494)
Quail (FooDB: FOOD00541)
Anatidae (FooDB: FOOD00576)
Rock ptarmigan (FooDB: FOOD00597)
Columbidae (Dove, Pigeon) (FooDB: FOOD00610)
Chicken (FooDB: FOOD00329)
Mallard duck (FooDB: FOOD00353)
Emu (FooDB: FOOD00360)
Greylag goose (FooDB: FOOD00368)
Guinea hen (FooDB: FOOD00373)
Ostrich (FooDB: FOOD00422)
Velvet duck (FooDB: FOOD00427)

Lagomorph

Ovis

Sheep (Mutton, Lamb) (FooDB: FOOD00473)

Bovine

Venison

Deer (FooDB: FOOD00524)
Mule deer (FooDB: FOOD00348)
Elk (FooDB: FOOD00359)

Caprae

Domestic goat (FooDB: FOOD00529)

Swine

Domestic pig (FooDB: FOOD00536)
Wild boar (FooDB: FOOD00307)

Equine

Horse (FooDB: FOOD00378)

Endogenous

Endogenous (HMDB: HMDB0004236)

Process

Naturally occurring process

Biological process

Biochemical pathway

Disease pathway

Leukotriene C4 Synthesis Deficiency (PathBank: SMP0120510)

Metabolic pathway

Arachidonic Acid Metabolism (PathBank: SMP0087315)

Drug action pathway

Piroxicam Action Pathway (PathBank: SMP0000077)
Acetylsalicylic Acid Action Pathway (PathBank: SMP0000083)
Etodolac Action Pathway (PathBank: SMP0000084)
Ketoprofen Action Pathway (PathBank: SMP0000085)
Ibuprofen Action Pathway (PathBank: SMP0000086)
Rofecoxib Action Pathway (PathBank: SMP0000087)
Diclofenac Action Pathway (PathBank: SMP0000093)
Sulindac Action Pathway (PathBank: SMP0000094)
Celecoxib Action Pathway (PathBank: SMP0000096)
Ketorolac Action Pathway (PathBank: SMP0000098)
Suprofen Action Pathway (PathBank: SMP0000101)
Bromfenac Action Pathway (PathBank: SMP0000102)
Indomethacin Action Pathway (PathBank: SMP0000104)
Mefenamic Acid Action Pathway (PathBank: SMP0000109)
Oxaprozin Action Pathway (PathBank: SMP0000113)
Nabumetone Action Pathway (PathBank: SMP0000114)
Naproxen Action Pathway (PathBank: SMP0000120)
Diflunisal Action Pathway (PathBank: SMP0000289)
Meloxicam Action Pathway (PathBank: SMP0000106)
Valdecoxib Action Pathway (PathBank: SMP0000116)
Antipyrine Action Pathway (PathBank: SMP0000692)
Antrafenine Action Pathway (PathBank: SMP0000693)
Carprofen Action Pathway (PathBank: SMP0000694)
Etoricoxib Action Pathway (PathBank: SMP0000695)
Fenoprofen Action Pathway (PathBank: SMP0000696)
Flurbiprofen Action Pathway (PathBank: SMP0000697)
Magnesium salicylate Action Pathway (PathBank: SMP0000698)
Lumiracoxib Action Pathway (PathBank: SMP0000699)
Lornoxicam Action Pathway (PathBank: SMP0000700)
Phenylbutazone Action Pathway (PathBank: SMP0000701)
Nepafenac Action Pathway (PathBank: SMP0000702)
Trisalicylate-choline Action Pathway (PathBank: SMP0000703)
Tolmetin Action Pathway (PathBank: SMP0000704)
Tiaprofenic Acid Action Pathway (PathBank: SMP0000705)
Tenoxicam Action Pathway (PathBank: SMP0000706)
Salsalate Action Pathway (PathBank: SMP0000707)
Salicylate-sodium Action Pathway (PathBank: SMP0000708)
Salicylic Acid Action Pathway (PathBank: SMP0000709)
Acetaminophen Action Pathway (PathBank: SMP0000710)

Role

Industrial application

Pharmaceutical industry

Biomarker

Stroke (MarkerDB: MDB00013451)

Physical Properties

State

Solid

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	3.154	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.03 g/L	ALOGPS
logP	4.07	ALOGPS
logP	4.18	ChemAxon
logS	-4	ALOGPS
pKa (Strongest Acidic)	4.25	ChemAxon
pKa (Strongest Basic)	-1.6	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	74.6 Å²	ChemAxon
Rotatable Bond Count	12	ChemAxon
Refractivity	98.61 m³·mol⁻¹	ChemAxon
Polarizability	39.64 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DeepCCS	[M+H]+	195.051	30932474
DeepCCS	[M-H]-	192.259	30932474
DeepCCS	[M-2H]-	226.986	30932474
DeepCCS	[M+Na]+	202.213	30932474
AllCCS	[M+H]+	188.2	32859911
AllCCS	[M+H-H2O]+	185.4	32859911
AllCCS	[M+NH4]+	190.8	32859911
AllCCS	[M+Na]+	191.5	32859911
AllCCS	[M-H]-	188.2	32859911
AllCCS	[M+Na-2H]-	189.5	32859911
AllCCS	[M+HCOO]-	191.1	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	8.35 minutes	32390414
Predicted by Siyang on May 30, 2022	17.6173 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	0.85 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	34.9 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	2727.4 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	352.9 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	194.7 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	201.4 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	425.5 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	756.8 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	573.4 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	115.5 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1708.4 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	554.4 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	1501.6 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	539.8 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	438.5 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	342.0 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	425.7 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	8.1 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Prostaglandin B2	CCCCC[C@@H](O)\C=C\C1=C(C\C=C/CCCC(O)=O)C(=O)CC1	4368.5	Standard polar	33892256
Prostaglandin B2	CCCCC[C@@H](O)\C=C\C1=C(C\C=C/CCCC(O)=O)C(=O)CC1	2717.1	Standard non polar	33892256
Prostaglandin B2	CCCCC[C@@H](O)\C=C\C1=C(C\C=C/CCCC(O)=O)C(=O)CC1	2864.1	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Prostaglandin B2,1TMS,isomer #1	CCCCC[C@H](/C=C/C1=C(C/C=C\CCCC(=O)O)C(=O)CC1)O[Si](C)(C)C	2887.3	Semi standard non polar	33892256
Prostaglandin B2,1TMS,isomer #2	CCCCC[C@@H](O)/C=C/C1=C(C/C=C\CCCC(=O)O[Si](C)(C)C)C(=O)CC1	2819.0	Semi standard non polar	33892256
Prostaglandin B2,1TMS,isomer #3	CCCCC[C@@H](O)/C=C/C1=C(C/C=C\CCCC(=O)O)C(O[Si](C)(C)C)=CC1	2862.8	Semi standard non polar	33892256
Prostaglandin B2,2TMS,isomer #1	CCCCC[C@H](/C=C/C1=C(C/C=C\CCCC(=O)O[Si](C)(C)C)C(=O)CC1)O[Si](C)(C)C	2855.1	Semi standard non polar	33892256
Prostaglandin B2,2TMS,isomer #2	CCCCC[C@H](/C=C/C1=C(C/C=C\CCCC(=O)O)C(O[Si](C)(C)C)=CC1)O[Si](C)(C)C	2900.6	Semi standard non polar	33892256
Prostaglandin B2,2TMS,isomer #3	CCCCC[C@@H](O)/C=C/C1=C(C/C=C\CCCC(=O)O[Si](C)(C)C)C(O[Si](C)(C)C)=CC1	2838.8	Semi standard non polar	33892256
Prostaglandin B2,3TMS,isomer #1	CCCCC[C@H](/C=C/C1=C(C/C=C\CCCC(=O)O[Si](C)(C)C)C(O[Si](C)(C)C)=CC1)O[Si](C)(C)C	2859.7	Semi standard non polar	33892256
Prostaglandin B2,3TMS,isomer #1	CCCCC[C@H](/C=C/C1=C(C/C=C\CCCC(=O)O[Si](C)(C)C)C(O[Si](C)(C)C)=CC1)O[Si](C)(C)C	2758.5	Standard non polar	33892256
Prostaglandin B2,3TMS,isomer #1	CCCCC[C@H](/C=C/C1=C(C/C=C\CCCC(=O)O[Si](C)(C)C)C(O[Si](C)(C)C)=CC1)O[Si](C)(C)C	3005.4	Standard polar	33892256
Prostaglandin B2,1TBDMS,isomer #1	CCCCC[C@H](/C=C/C1=C(C/C=C\CCCC(=O)O)C(=O)CC1)O[Si](C)(C)C(C)(C)C	3115.1	Semi standard non polar	33892256
Prostaglandin B2,1TBDMS,isomer #2	CCCCC[C@@H](O)/C=C/C1=C(C/C=C\CCCC(=O)O[Si](C)(C)C(C)(C)C)C(=O)CC1	3056.1	Semi standard non polar	33892256
Prostaglandin B2,1TBDMS,isomer #3	CCCCC[C@@H](O)/C=C/C1=C(C/C=C\CCCC(=O)O)C(O[Si](C)(C)C(C)(C)C)=CC1	3096.0	Semi standard non polar	33892256
Prostaglandin B2,2TBDMS,isomer #1	CCCCC[C@H](/C=C/C1=C(C/C=C\CCCC(=O)O[Si](C)(C)C(C)(C)C)C(=O)CC1)O[Si](C)(C)C(C)(C)C	3353.0	Semi standard non polar	33892256
Prostaglandin B2,2TBDMS,isomer #2	CCCCC[C@H](/C=C/C1=C(C/C=C\CCCC(=O)O)C(O[Si](C)(C)C(C)(C)C)=CC1)O[Si](C)(C)C(C)(C)C	3356.5	Semi standard non polar	33892256
Prostaglandin B2,2TBDMS,isomer #3	CCCCC[C@@H](O)/C=C/C1=C(C/C=C\CCCC(=O)O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)=CC1	3322.3	Semi standard non polar	33892256
Prostaglandin B2,3TBDMS,isomer #1	CCCCC[C@H](/C=C/C1=C(C/C=C\CCCC(=O)O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)=CC1)O[Si](C)(C)C(C)(C)C	3567.2	Semi standard non polar	33892256
Prostaglandin B2,3TBDMS,isomer #1	CCCCC[C@H](/C=C/C1=C(C/C=C\CCCC(=O)O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)=CC1)O[Si](C)(C)C(C)(C)C	3164.7	Standard non polar	33892256
Prostaglandin B2,3TBDMS,isomer #1	CCCCC[C@H](/C=C/C1=C(C/C=C\CCCC(=O)O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)=CC1)O[Si](C)(C)C(C)(C)C	3183.1	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Prostaglandin B2 GC-MS (Non-derivatized) - 70eV, Positive	splash10-00lm-6391000000-3b069d42dd8ba363e1c3	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Prostaglandin B2 GC-MS (2 TMS) - 70eV, Positive	splash10-020c-9107400000-3e378b304e81c9767275	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Prostaglandin B2 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 B2 10V, Positive-QTOF	splash10-014j-0169000000-ab7e151e7512a9217570	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Prostaglandin B2 20V, Positive-QTOF	splash10-02ga-3951000000-6eb2a7a228914281a6f5	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Prostaglandin B2 40V, Positive-QTOF	splash10-0f76-9220000000-0ee4fdc9b2a755b944e0	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Prostaglandin B2 10V, Negative-QTOF	splash10-001i-0019000000-dbe0b0e74e1f3b041bda	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Prostaglandin B2 20V, Negative-QTOF	splash10-0159-2159000000-e67ebc50c5d1f2b7f75f	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Prostaglandin B2 40V, Negative-QTOF	splash10-0a4l-9140000000-dc05680aa61a1ac55903	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Prostaglandin B2 10V, Negative-QTOF	splash10-0159-0029000000-9e6efa43b3e01f68d9d3	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Prostaglandin B2 20V, Negative-QTOF	splash10-00lr-1397000000-82f85934c72172d6f0bd	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Prostaglandin B2 40V, Negative-QTOF	splash10-05mo-7931000000-b9dc32b05b5d304a8c15	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Prostaglandin B2 10V, Positive-QTOF	splash10-00kb-0095000000-ec2f02e0ccce84d13240	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Prostaglandin B2 20V, Positive-QTOF	splash10-00kb-4291000000-c675b9e2faa54ccca098	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Prostaglandin B2 40V, Positive-QTOF	splash10-00nf-9510000000-f147c78bdfdeae923ab0	2021-09-25	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Extracellular
Membrane

Biospecimen Locations

Blood
Cerebrospinal Fluid (CSF)

Tissue Locations

Not Available

Pathways

Name	SMPDB/PathBank	KEGG
Arachidonic Acid Metabolism
Leukotriene C4 Synthesis Deficiency		Not Available
Piroxicam Action Pathway		Not Available
Acetylsalicylic Acid Action Pathway		Not Available
Etodolac Action Pathway		Not Available

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected and Quantified	0.000373 +/- 0.000212 uM	Adult (>18 years old)	Both	Normal	18953024 21359215	details
Blood	Detected and Quantified	0.000519 +/- 0.000096 uM	Adult (>18 years old)	Both	Normal	21359215	details
Blood	Detected and Quantified	<0.0007 uM	Adult (>18 years old)	Both	Normal	21359215	details
Cerebrospinal Fluid (CSF)	Detected and Quantified	0.0000002992 uM	Not Specified	Not Specified	Normal	3791712	details

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Cerebrospinal Fluid (CSF)	Detected and Quantified	0.0000004488 uM	Not Specified	Not Specified	ischaemic stroke	3791712	details

Associated Disorders and Diseases

Disease References

Cerebral infarction
Fagan SC, Castellani D, Gengo FM: Prostanoid concentrations in human CSF following acute ischaemic brain infarction. Clin Exp Pharmacol Physiol. 1986 Aug;13(8):629-32. [PubMed:3791712 ]

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB023342

KNApSAcK ID

Not Available

Chemspider ID

4450370

KEGG Compound ID

C05954

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

5288144

PDB ID

E2P

ChEBI ID

28099

Food Biomarker Ontology

Not Available

VMH ID

HC02205

MarkerDB ID

MDB00013451

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Download (PDF)

General References

Masoodi M, Nicolaou A: Lipidomic analysis of twenty-seven prostanoids and isoprostanes by liquid chromatography/electrospray tandem mass spectrometry. Rapid Commun Mass Spectrom. 2006;20(20):3023-9. [PubMed:16986207 ]

Showing metabocard for Prostaglandin B2 (HMDB0004236)

MOL for HMDB0004236 (Prostaglandin B2)

3D MOL for HMDB0004236 (Prostaglandin B2)

3D SDF for HMDB0004236 (Prostaglandin B2)

3D-SDF for HMDB0004236 (Prostaglandin B2)

PDB for HMDB0004236 (Prostaglandin B2)

3D PDB for HMDB0004236 (Prostaglandin B2)

SMILES for HMDB0004236 (Prostaglandin B2)

INCHI for HMDB0004236 (Prostaglandin B2)

Structure for HMDB0004236 (Prostaglandin B2)

3D Structure for HMDB0004236 (Prostaglandin B2)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra