ChemFOnt: Showing chemical card for (5E)-5-[(3Ar,4S,5S,6aR)-5-hydroxy-4-[(E,3R)-3-hydroxyoct-1-enyl]-3,3a,4,5,6,6a-hexahydro-1H-pentalen-2-ylidene]pentanoic acid (CFc000226743)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-14 01:51:14 UTC

Chemfont ID

CFc000226743

Molecule Identification

Common Name

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

Definition

(5E)-5-[(3Ar,4S,5S,6aR)-5-hydroxy-4-[(E,3R)-3-hydroxyoct-1-enyl]-3,3a,4,5,6,6a-hexahydro-1H-pentalen-2-ylidene]pentanoic acid, also known as carba-prostacyclin or (5E)-6a-carba-prostaglandin I2, belongs to the class of organic compounds known as prostaglandins and related compounds. These are unsaturated carboxylic acids consisting of a 20 carbon skeleton that also contains a five member ring, and are based upon the fatty acid arachidonic acid. Based on a literature review a significant number of articles have been published on (5E)-5-[(3Ar,4S,5S,6aR)-5-hydroxy-4-[(E,3R)-3-hydroxyoct-1-enyl]-3,3a,4,5,6,6a-hexahydro-1H-pentalen-2-ylidene]pentanoic acid.

Structure

MOL SDF PDB SMILES InChI

Synonyms

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

Chemical Formula

C₂₁H₃₄O₄

Average Molecular Weight

350.499

Monoisotopic Molecular Weight

350.245709575

IUPAC Name

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

Traditional Name

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

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

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

InChI Key

XZFRIPGNUQRGPI-UHFFFAOYSA-N

Chemical Taxonomy

Description

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

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Eicosanoids

Direct Parent

Prostaglandins and related compounds

Alternative Parents

Substituents

Prostaglandin skeleton
Bicyclic monoterpenoid
Monoterpenoid
Fatty alcohol
Medium-chain hydroxy acid
Medium-chain fatty acid
Hydroxy fatty acid
Cyclic alcohol
Secondary alcohol
Monocarboxylic acid or derivatives
Carboxylic acid
Carboxylic acid derivative
Hydrocarbon derivative
Organooxygen compound
Organic oxide
Alcohol
Carbonyl group
Organic oxygen compound
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

Not Available

Functional Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 31557052)

Source

Exogenous

Exogenous (PMID: 31557052)

Process

Not Available

Role

Not Available

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	0.055 g/L	ALOGPS
logP	4.7	ALOGPS
logP	3.61	ChemAxon
logS	-3.8	ALOGPS
pKa (Strongest Acidic)	4.66	ChemAxon
pKa (Strongest Basic)	-0.92	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	77.76 Å²	ChemAxon
Rotatable Bond Count	10	ChemAxon
Refractivity	101.35 m³·mol⁻¹	ChemAxon
Polarizability	41.99 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0247207

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

2455

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

2552

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

Showing chemical card for (5E)-5-[(3Ar,4S,5S,6aR)-5-hydroxy-4-[(E,3R)-3-hydroxyoct-1-enyl]-3,3a,4,5,6,6a-hexahydro-1H-pentalen-2-ylidene]pentanoic acid (CFc000226743)

MOL for CFc000226743 ((5E)-5-[(3Ar,4S,5S,6aR)-5-hydroxy-4-[(E,3R)-3-hydroxyoct-1-enyl]-3,3a,4,5,6,6a-hexahydro-1H-pentalen-2-ylidene]pentanoic acid)

3D MOL for CFc000226743 ((5E)-5-[(3Ar,4S,5S,6aR)-5-hydroxy-4-[(E,3R)-3-hydroxyoct-1-enyl]-3,3a,4,5,6,6a-hexahydro-1H-pentalen-2-ylidene]pentanoic acid)

3D SDF for CFc000226743 ((5E)-5-[(3Ar,4S,5S,6aR)-5-hydroxy-4-[(E,3R)-3-hydroxyoct-1-enyl]-3,3a,4,5,6,6a-hexahydro-1H-pentalen-2-ylidene]pentanoic acid)

3D-SDF for CFc000226743 ((5E)-5-[(3Ar,4S,5S,6aR)-5-hydroxy-4-[(E,3R)-3-hydroxyoct-1-enyl]-3,3a,4,5,6,6a-hexahydro-1H-pentalen-2-ylidene]pentanoic acid)

PDB for CFc000226743 ((5E)-5-[(3Ar,4S,5S,6aR)-5-hydroxy-4-[(E,3R)-3-hydroxyoct-1-enyl]-3,3a,4,5,6,6a-hexahydro-1H-pentalen-2-ylidene]pentanoic acid)

3D PDB for CFc000226743 ((5E)-5-[(3Ar,4S,5S,6aR)-5-hydroxy-4-[(E,3R)-3-hydroxyoct-1-enyl]-3,3a,4,5,6,6a-hexahydro-1H-pentalen-2-ylidene]pentanoic acid)

SMILES for CFc000226743 ((5E)-5-[(3Ar,4S,5S,6aR)-5-hydroxy-4-[(E,3R)-3-hydroxyoct-1-enyl]-3,3a,4,5,6,6a-hexahydro-1H-pentalen-2-ylidene]pentanoic acid)

INCHI for CFc000226743 ((5E)-5-[(3Ar,4S,5S,6aR)-5-hydroxy-4-[(E,3R)-3-hydroxyoct-1-enyl]-3,3a,4,5,6,6a-hexahydro-1H-pentalen-2-ylidene]pentanoic acid)

Structure for CFc000226743 ((5E)-5-[(3Ar,4S,5S,6aR)-5-hydroxy-4-[(E,3R)-3-hydroxyoct-1-enyl]-3,3a,4,5,6,6a-hexahydro-1H-pentalen-2-ylidene]pentanoic acid)

3D Structure for CFc000226743 ((5E)-5-[(3Ar,4S,5S,6aR)-5-hydroxy-4-[(E,3R)-3-hydroxyoct-1-enyl]-3,3a,4,5,6,6a-hexahydro-1H-pentalen-2-ylidene]pentanoic acid)