Bovine Metabolome Database: Showing metabocard for Prostaglandin E1 (BMDB0001442)

Identification Taxonomy Physical properties Pathways Spectra Concentrations Links References XML

Record Information

Version

1.0

Creation Date

2016-09-30 22:46:02 UTC

Update Date

2020-05-11 20:44:46 UTC

BMDB ID

BMDB0001442

Secondary Accession Numbers

BMDB01442

Metabolite Identification

Common Name

Prostaglandin E1

Description

Prostaglandin E1, also known as alprostadil or caverject, 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 E1 is considered to be an eicosanoid. Based on a literature review a small amount of articles have been published on Prostaglandin E1.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
(11alpha,13E,15S)-11,15-Dihydroxy-9-oxoprost-13-en-1-Oic acid	ChEBI
(13E)-(15S)-11alpha,15-Dihydroxy-9-oxoprost-13-enoate	ChEBI
11alpha,15alpha-Dihydroxy-9-oxo-13-trans-prostenoic acid	ChEBI
Alprostadil	ChEBI
Alprostadilum	ChEBI
Befar	ChEBI
Caverject	ChEBI
Edex	ChEBI
Muse	ChEBI
PGE-1	ChEBI
PGE1	ChEBI
Prostin VR	ChEBI
Prostin VR pediatric	Kegg
(11a,13E,15S)-11,15-Dihydroxy-9-oxoprost-13-en-1-Oate	Generator
(11a,13E,15S)-11,15-Dihydroxy-9-oxoprost-13-en-1-Oic acid	Generator
(11alpha,13E,15S)-11,15-Dihydroxy-9-oxoprost-13-en-1-Oate	Generator
(11Α,13E,15S)-11,15-dihydroxy-9-oxoprost-13-en-1-Oate	Generator
(11Α,13E,15S)-11,15-dihydroxy-9-oxoprost-13-en-1-Oic acid	Generator
(13E)-(15S)-11a,15-Dihydroxy-9-oxoprost-13-enoate	Generator
(13E)-(15S)-11a,15-Dihydroxy-9-oxoprost-13-enoic acid	Generator
(13E)-(15S)-11alpha,15-Dihydroxy-9-oxoprost-13-enoic acid	Generator
(13E)-(15S)-11Α,15-dihydroxy-9-oxoprost-13-enoate	Generator
(13E)-(15S)-11Α,15-dihydroxy-9-oxoprost-13-enoic acid	Generator
11a,15a-Dihydroxy-9-oxo-13-trans-prostenoate	Generator
11a,15a-Dihydroxy-9-oxo-13-trans-prostenoic acid	Generator
11alpha,15alpha-Dihydroxy-9-oxo-13-trans-prostenoate	Generator
11Α,15α-dihydroxy-9-oxo-13-trans-prostenoate	Generator
11Α,15α-dihydroxy-9-oxo-13-trans-prostenoic acid	Generator
Abbott brand OF alprostadil	MeSH, HMDB
Minprog	MeSH, HMDB
Paladin brand OF alprostadil	MeSH, HMDB
Prostaglandin e1alpha	MeSH, HMDB
Schwarz pharma brand OF alprostadil	MeSH, HMDB
Astra brand OF alprostadil	MeSH, HMDB
Hoyer brand OF alprostadil	MeSH, HMDB
Sugiran	MeSH, HMDB
Allphar brand OF alprostadil	MeSH, HMDB
AstraZeneca brand OF alprostadil	MeSH, HMDB
lipo PGE1	MeSH, HMDB
Viridal	MeSH, HMDB
lipo-PGE1	MeSH, HMDB
Vasaprostan	MeSH, HMDB
Janssen brand OF alprostadil	MeSH, HMDB
PGE1alpha	MeSH, HMDB
Pharmacia brand 1 OF alprostadil	MeSH, HMDB
Prostavasin	MeSH, HMDB
Prostine VR	MeSH, HMDB
Pharmacia brand 2 OF alprostadil	MeSH, HMDB
Prostaglandin e1	MeSH, KEGG
Schwarz brand OF alprostadil	MeSH, HMDB
Vivus brand OF alprostadil	MeSH, HMDB
Prink	KEGG, HMDB
Vitaros	KEGG, HMDB
Caverject impulse	ChEMBL, HMDB
U-10136prostin	ChEMBL, HMDB
U-10136alprostadil	ChEMBL, HMDB
(+)-3-Hydroxy-2-(3-hydroxy-1-octenyl)-5-oxo-cyclopentaneheptanoate	HMDB
(+)-3-Hydroxy-2-(3-hydroxy-1-octenyl)-5-oxo-cyclopentaneheptanoic acid	HMDB
(-)-3-Hydroxy-2-(3-hydroxy-1-octenyl)-5-oxo-cyclopentaneheptanoate	HMDB
(-)-3-Hydroxy-2-(3-hydroxy-1-octenyl)-5-oxo-cyclopentaneheptanoic acid	HMDB
(-)-Prostaglandin e1	HMDB
(13E)-(15S)-11,15-Dihydroxy-9-oxoprost-13-enoate	HMDB
(13E)-(15S)-11,15-Dihydroxy-9-oxoprost-13-enoic acid	HMDB
(13E)-(15S)-11-alpha,15-Dihydroxy-9-oxoprost-13-enoate	HMDB
(13E)-(15S)-11-alpha,15-Dihydroxy-9-oxoprost-13-enoic acid	HMDB
11,15-Dihydroxy-9-oxoprost-13-en-1-Oate	HMDB
11,15-Dihydroxy-9-oxoprost-13-en-1-Oic acid	HMDB
11,15-Dihydroxy-9-oxoprost-13-en-1-Oic acid (acd/name 4.0)	HMDB
3-Hydroxy-2-(3-hydroxy-1-octenyl)-5-oxo-cyclopentaneheptanoate	HMDB
3-Hydroxy-2-(3-hydroxy-1-octenyl)-5-oxo-cyclopentaneheptanoic acid	HMDB
Alprostadil prostoglandin e1	HMDB
Alprostadil(usan)	HMDB
L-Prostaglandin e1	HMDB

Chemical Formula

C₂₀H₃₄O₅

Average Molecular Weight

354.487

Monoisotopic Molecular Weight

354.240624195

IUPAC Name

7-[(1R,2R,3R)-3-hydroxy-2-[(1E,3S)-3-hydroxyoct-1-en-1-yl]-5-oxocyclopentyl]heptanoic acid

Traditional Name

alprostadil

CAS Registry Number

745-65-3

SMILES

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

InChI Identifier

InChI=1S/C20H34O5/c1-2-3-6-9-15(21)12-13-17-16(18(22)14-19(17)23)10-7-4-5-8-11-20(24)25/h12-13,15-17,19,21,23H,2-11,14H2,1H3,(H,24,25)/b13-12+/t15-,16+,17+,19+/m0/s1

InChI Key

GMVPRGQOIOIIMI-DWKJAMRDSA-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
Fatty alcohol
Hydroxy fatty acid
Cyclopentanol
Cyclic alcohol
Cyclic ketone
Ketone
Secondary alcohol
Carboxylic acid
Carboxylic acid derivative
Monocarboxylic acid or derivatives
Alcohol
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Carbonyl group
Organooxygen compound
Aliphatic homomonocyclic compound

Molecular Framework

Aliphatic homomonocyclic compounds

External Descriptors

prostaglandins E (CHEBI:15544 )
Prostaglandins (C04741 )
Prostaglandins (LMFA03010134 )

Ontology

Status

Detected but not Quantified

Origin

Endogenous

Exogenous

Biofunction

Not Available

Application

Not Available

Cellular locations

Cell membrane
Cytoplasm
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	3.59	ChemAxon
pKa (Strongest Acidic)	4.35	ChemAxon
pKa (Strongest Basic)	-1.6	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	94.83 Å²	ChemAxon
Rotatable Bond Count	13	ChemAxon
Refractivity	98.32 m³·mol⁻¹	ChemAxon
Polarizability	42.13 Å³	ChemAxon
Number of Rings	1	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	Not Available	View in JSpectraViewer
LC-MS/MS	LC-MS/MS Spectrum - 35V, Negative	splash10-00ri-0196000000-76a244edad65f2d63bd5	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-00kr-0019000000-8df8823c74db989620bf	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0673-4297000000-470e93d0689f9efe2bf4	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-06du-9120000000-617b73c4fa8e71daf174	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0udi-0019000000-67bf705be88aef628788	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0k9l-2159000000-ea5fde7ba374a4b745ac	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4i-9420000000-64831d7733e0f1578bc7	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0fri-0009000000-923c8a53409a3df92c03	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-000i-0069000000-1771266ae55287330e24	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-001v-9481000000-4f3fb6bba04c2db22a67	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-014i-0009000000-48b67d3860a0408d6017	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-014i-7369000000-67c0756e11758bfc63bd	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-05mo-9600000000-b116946f56f764ec762e	View in MoNA

Biological Properties

Cellular Locations

Cell membrane
Cytoplasm
Membrane

Biospecimen Locations

Epidermis
Fibroblasts
Kidney
Liver
Neuron
Placenta
Platelet

Pathways

Not Available

Name	SMPDB/Pathwhiz	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Epidermis	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	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	PMID: 31867104	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

HMDB0001442

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

4444306

KEGG Compound ID

C04741

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Prostaglandin_E1

METLIN ID

Not Available

PubChem Compound

5280723

PDB ID

Not Available

ChEBI ID

15544

References

Synthesis Reference

Liang, Yong-tao; Wei, Feng-ping; Li, Gui-ying; Wang, En-si. Chemoenzymic synthesis of prostaglandin E1. Jilin Daxue Ziran Kexue Xuebao (2001), (2), 77-80.

Material Safety Data Sheet (MSDS)

Not Available

General References

Not Available

Showing metabocard for Prostaglandin E1 (BMDB0001442)

Structure for BMDB0001442 (Prostaglandin E1)