Bovine Metabolome Database: Showing metabocard for Prostaglandin I2 (BMDB0001335)

Identification Taxonomy Physical properties Pathways Spectra Concentrations Links References enzymes (2) Show 2 proteins XML

Record Information

Version

1.0

Creation Date

2016-09-30 22:44:17 UTC

Update Date

2020-05-20 23:10:00 UTC

BMDB ID

BMDB0001335

Secondary Accession Numbers

BMDB01335

Metabolite Identification

Common Name

Prostaglandin I2

Description

Prostaglandin i2, also known as prostaglandin I2 or prostaglandin I2, belongs to the class of organic compounds known as prostaglandins and related compounds. These are unsaturated carboxylic acids consisting of a 20 carbon skeleton that also contains a five member ring, and are based upon the fatty acid arachidonic acid. Thus, prostaglandin I2 is considered to be an eicosanoid lipid molecule. Prostaglandin i2 is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Prostaglandin i2 exists in all living organisms, ranging from bacteria to humans. Prostaglandin i2 participates in a number of enzymatic reactions, within cattle. In particular, Prostaglandin I2 can be converted into prostaglandin I2 through the action of the enzyme prostaglandin I2 receptor. In addition, Prostaglandin I2 can be converted into prostaglandin I2 through the action of the enzyme prostaglandin I2 receptor. In cattle, prostaglandin I2 is involved in the metabolic pathway called the intracellular signalling through prostaglandin I2 receptor and prostaglandin I2 pathway.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
(5Z,13E)-(15S)-6,9alpha-Epoxy-11alpha,15-dihydroxyprosta-5,13-dienoate	ChEBI
(5Z,9alpha,11alpha,13E,15S)-6,9-Epoxy-11,15-dihydroxyprosta-5,13-dien-1-Oic acid	ChEBI
Epoprostenol	ChEBI
Flolan	ChEBI
PGI2	ChEBI
PGX	ChEBI
Prostacyclin	ChEBI
Prostaglandin X	ChEBI
Vasocyclin	ChEBI
(5Z,13E)-(15S)-6,9a-Epoxy-11a,15-dihydroxyprosta-5,13-dienoate	Generator
(5Z,13E)-(15S)-6,9a-Epoxy-11a,15-dihydroxyprosta-5,13-dienoic acid	Generator
(5Z,13E)-(15S)-6,9alpha-Epoxy-11alpha,15-dihydroxyprosta-5,13-dienoic acid	Generator
(5Z,13E)-(15S)-6,9Α-epoxy-11α,15-dihydroxyprosta-5,13-dienoate	Generator
(5Z,13E)-(15S)-6,9Α-epoxy-11α,15-dihydroxyprosta-5,13-dienoic acid	Generator
(5Z,9a,11a,13E,15S)-6,9-Epoxy-11,15-dihydroxyprosta-5,13-dien-1-Oate	Generator
(5Z,9a,11a,13E,15S)-6,9-Epoxy-11,15-dihydroxyprosta-5,13-dien-1-Oic acid	Generator
(5Z,9alpha,11alpha,13E,15S)-6,9-Epoxy-11,15-dihydroxyprosta-5,13-dien-1-Oate	Generator
(5Z,9Α,11α,13E,15S)-6,9-epoxy-11,15-dihydroxyprosta-5,13-dien-1-Oate	Generator
(5Z,9Α,11α,13E,15S)-6,9-epoxy-11,15-dihydroxyprosta-5,13-dien-1-Oic acid	Generator
(5Z,13E)-(15S)-6,9-alpha-Epoxy-11-alpha,15-dihydroxyprosta-5,13-dienoate	HMDB
(5Z,13E)-(15S)-6,9-alpha-Epoxy-11-alpha,15-dihydroxyprosta-5,13-dienoic acid	HMDB
(5Z,13E)-(15S)-6,9-Epoxy-11,15-dihydroxyprosta-5,13-dienoate	HMDB
(5Z,13E)-(15S)-6,9-Epoxy-11,15-dihydroxyprosta-5,13-dienoic acid	HMDB
(5Z,13E,15S)-6,9a-Epoxy-11a,15-dihydroxyprosta-5,13-dienoate	HMDB
(5Z,13E,15S)-6,9a-Epoxy-11a,15-dihydroxyprosta-5,13-dienoic acid	HMDB
Prostacycline	HMDB
Epoprostanol	HMDB
Epoprostenol sodium	HMDB
Epoprostenol sodium salt, (5Z,9alpha,11alpha,13E,15S)-isomer	HMDB
Prostaglandin I(2)	HMDB
Veletri	MeSH

Chemical Formula

C₂₀H₃₂O₅

Average Molecular Weight

352.4651

Monoisotopic Molecular Weight

352.224974134

IUPAC Name

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

Traditional Name

epoprostenol

CAS Registry Number

35121-78-9

SMILES

CCCCC[C@H](O)\C=C\[C@H]1[C@H](O)C[C@@H]2OC(C[C@H]12)=CCCCC(O)=O

InChI Identifier

InChI=1S/C20H32O5/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/h8,10-11,14,16-19,21-22H,2-7,9,12-13H2,1H3,(H,23,24)/b11-10+,15-8-/t14-,16+,17+,18+,19-/m0/s1

InChI Key

KAQKFAOMNZTLHT-OZUDYXHBSA-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

prostaglandins I (CHEBI:15552 )
Prostaglandins (C01312 )
Prostaglandins (LMFA03010087 )

Ontology

Status

Expected but not Quantified

Origin

Endogenous

Exogenous

Biofunction

Not Available

Application

Not Available

Cellular locations

Cell membrane
Cytoplasm
Endoplasmic reticulum
Membrane

Physical Properties

State

Solid

Experimental 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

Predicted Properties

Property	Value	Source
logP	3.83	ALOGPS
logP	2.42	ChemAxon
logS	-3.4	ALOGPS
pKa (Strongest Acidic)	4.43	ChemAxon
pKa (Strongest Basic)	-1.6	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	10	ChemAxon
Refractivity	99.01 m³·mol⁻¹	ChemAxon
Polarizability	41.47 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Spectra

Spectrum Type	Description	Splash Key
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0159-5693000000-d4cdd32893c86bb9479a	View in MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positive	splash10-0ug0-9253570000-9f0d8bdb642b0c32f40b	View in MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-00kr-0029000000-6c6186798558c5d1611f	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-00y0-1093000000-eacafc8768142dba71da	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-00du-9450000000-e3b550dcd32e28648707	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0udi-0009000000-34a4a3eaa1abb59e8245	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0f89-2139000000-efe90037816a750cfeee	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a59-9871000000-f961005fef0ef2363ce4	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0udi-0009000000-39b83b5b9b932bb2f6a1	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0ue9-0089000000-7141693b6303cf4e2e29	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-003s-2391000000-22e55e30c5e2afce8cc2	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-014r-0009000000-fcc9a31a4c60d564196f	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-014i-6359000000-d638f048af6abdb45cbf	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-05tf-9610000000-8baf1f1acd84f0ed7ba8	View in MoNA

Biological Properties

Cellular Locations

Cell membrane
Cytoplasm
Endoplasmic reticulum
Membrane

Biospecimen Locations

Adipose Tissue
Bladder
Brain
Fibroblasts
Kidney
Liver
Neuron
Placenta
Platelet

Pathways

Name	SMPDB/Pathwhiz	KEGG
Arachidonic Acid Metabolism		Not Available
Intracellular Signalling Through Prostacyclin Receptor and Prostacyclin		Not Available

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Adipose Tissue	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	Not Applicable	details
Bladder	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	Not Applicable	details
Brain	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	Not Applicable	details
Fibroblasts	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	Not Applicable	details
Kidney	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	Not Applicable	details
Liver	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	Not Applicable	details
Neuron	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	Not Applicable	details
Placenta	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	Not Applicable	details
Platelet	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	Not Applicable	details

Abnormal Concentrations

Not Available

External Links

HMDB ID

HMDB0001335

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB022560

KNApSAcK ID

Not Available

Chemspider ID

4445566

KEGG Compound ID

C01312

BioCyc ID

Not Available

BiGG ID

Wikipedia Link

METLIN ID

PubChem Compound

PDB ID

Not Available

ChEBI ID

15552

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Not Available

Enzymes

Enzyme Details

1. Prostacyclin synthase

General function:: Secondary metabolites biosynthesis, transport and catabolism
Specific function:: Catalyzes the isomerization of prostaglandin H2 to prostacyclin (= prostaglandin I2).
Gene Name:: PTGIS
Uniprot ID:: Q29626
Molecular weight:: 56629.0

Reactions

Prostaglandin H2 → Prostaglandin I2	details

Enzyme Details

2. Prostacyclin receptor

General function:: Involved in G-protein coupled receptor activity
Specific function:: Receptor for prostacyclin (prostaglandin I2 or PGI2). The activity of this receptor is mediated by G(s) proteins which activate adenylate cyclase.
Gene Name:: PTGIR
Uniprot ID:: P79393
Molecular weight:: 41247.0

Showing metabocard for Prostaglandin I2 (BMDB0001335)

Structure for BMDB0001335 (Prostaglandin I2)

Enzymes

Reactions