prostaglandin A1

Details

• Internal ID: a2413a59-59fd-4713-9c3b-24a1cf09ca82
• Taxonomy: Lipids and lipid-like molecules > Fatty Acyls > Eicosanoids > Prostaglandins and related compounds
• IUPAC Name: 7-[(1R,2S)-2-[(E,3S)-3-hydroxyoct-1-enyl]-5-oxocyclopent-3-en-1-yl]heptanoic acid
• SMILES (Canonical): CCCCCC(C=CC1C=CC(=O)C1CCCCCCC(=O)O)O
• SMILES (Isomeric): CCCCC[C@@H](/C=C/[C@H]1C=CC(=O)[C@@H]1CCCCCCC(=O)O)O
• InChI: InChI=1S/C20H32O4/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/h12-18,21H,2-11H2,1H3,(H,23,24)/b14-12+/t16-,17-,18+/m0/s1
• InChI Key: BGKHCLZFGPIKKU-LDDQNKHRSA-N
• Popularity: 218 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₀H₃₂O₄
• Molecular Weight: 336.50 g/mol
• Exact Mass: 336.23005950 g/mol
• Topological Polar Surface Area (TPSA): 74.60 Ų
• XlogP: 4.40
• Atomic LogP (AlogP): 4.28
• H-Bond Acceptor: 3
• H-Bond Donor: 2
• Rotatable Bonds: 13

Synonyms

• PGA1
• 14152-28-4
• PGA(sub 1)
• PGA(sup 1)
• Prostaglandin A(sub 1)
• Prostaglandin A(sup 1)
• Prostaglandin E(sup 1)-217
• Prosta-10,13-dien-1-oic acid, 15-hydroxy-9-oxo-, (13E,15S)-
• PGA1 (Prostaglandin A1)
• UNII-VYR271N44P
• 15a-Hydroxy-9-oxo-10,13E-prostadienoate
• VYR271N44P
• (13E,15S)-15-hydroxy-9-oxoprosta-10,13-dien-1-oic acid
• CHEBI:15545
• 15a-Hydroxy-9-oxo-10,13E-prostadienoic acid
• 7-[(1R,2S)-2-[(E,3S)-3-hydroxyoct-1-enyl]-5-oxocyclopent-3-en-1-yl]heptanoic acid
• 9-oxo-15S-hydroxy-10Z,13E-prostadienoic acid
• 3-Cyclopentene-1-heptanoic acid, 2-(3-hydroxy-1-octenyl)-5-oxo-
• Prostaglandin E1-217
• CHEMBL1084644
• Prostaglandin A1, synthetic
• BSPBio_001458
• BML1-F01
• SCHEMBL6417548
• Eicosanoids_PGA1_C20H32O4
• PGA1, Prostaglandin A1, powder
• PROSTAGLANDIN A1 (PGA1)
• BGKHCLZFGPIKKU-LDDQNKHRSA-N
• DTXSID601347314
• HMS1361I20
• HMS1791I20
• HMS1989I20
• HMS3402I20
• HMS3648A03
• PROSTAGLANDIN A1 [USP-RS]
• (13E,15S)-15-hydroxy-9-oxo-Prosta-10,13-dien-1-oic acid
• LMFA03010005
• CCG-208253
• IDI1_033928
• NCGC00161282-01
• NCGC00161282-02
• NCGC00161282-03
• 15-hydroxy-9-oxoprosta-10,13-dienoate
• LS-58328
• 15a-Hydroxy-9-ketoprosta-10,13-dienoate
• 15-hydroxy-9-oxoprosta-10,13-dienoic acid
• ALPROSTADIL IMPURITY A [EP IMPURITY]
• 15a-Hydroxy-9-ketoprosta-10,13-dienoic acid
• SR-01000946186
• J-007508
• SR-01000946186-1
• BRD-K04010869-001-02-6
• Q27098093
• (13E,15S)-15-hydroxy-9-oxo-Prosta-10,13-dien-1-oate
• 9-OXO-15S-HYDROXY-PROSTA-10,13E-DIEN-1-OIC ACID
• 2-(3-hydroxy-1-octenyl)-5-oxo-3- cyclopentene-1-heptanoate
• 2-(3-hydroxy-1-octenyl)-5-oxo-3-Cyclopentene-1-heptanoate
• 2-(3-hydroxy-1-octenyl)-5-oxo-3- cyclopentene-1-heptanoic acid
• 2-(3-hydroxy-1-octenyl)-5-oxo-3-Cyclopentene-1-heptanoic acid
• PGA1 (Prostaglandin A1) is known as a Cyclopentenone prostaglandin.
• Prostaglandin A1, United States Pharmacopeia (USP) Reference Standard
• 7-((1R,2S)-2-((S,E)-3-hydroxyoct-1-enyl)-5-oxocyclopent-3-enyl)heptanoic acid
• 7-[(1R,2S)-2-[(E,3S)-3-hydroxyoct-1-enyl]-5-oxo-cyclopent-3-en-1-yl]heptanoic acid

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9711	97.11%
Caco-2	-	0.6812	68.12%
Blood Brain Barrier	-	0.8500	85.00%
Human oral bioavailability	-	0.8857	88.57%
Subcellular localzation	Mitochondria	0.8450	84.50%
OATP2B1 inhibitior	-	0.8557	85.57%
OATP1B1 inhibitior	+	0.8170	81.70%
OATP1B3 inhibitior	+	0.9399	93.99%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.9000	90.00%
BSEP inhibitior	-	0.7451	74.51%
P-glycoprotein inhibitior	-	0.7518	75.18%
P-glycoprotein substrate	-	0.7255	72.55%
CYP3A4 substrate	+	0.5150	51.50%
CYP2C9 substrate	-	0.5969	59.69%
CYP2D6 substrate	-	0.9037	90.37%
CYP3A4 inhibition	-	0.8693	86.93%
CYP2C9 inhibition	-	0.9564	95.64%
CYP2C19 inhibition	-	0.9240	92.40%
CYP2D6 inhibition	-	0.9210	92.10%
CYP1A2 inhibition	-	0.9008	90.08%
CYP2C8 inhibition	-	0.8280	82.80%
CYP inhibitory promiscuity	-	0.9693	96.93%
UGT catelyzed	-	0.7000	70.00%
Carcinogenicity (binary)	-	0.9500	95.00%
Carcinogenicity (trinary)	Non-required	0.7513	75.13%
Eye corrosion	-	0.9923	99.23%
Eye irritation	-	0.9393	93.93%
Skin irritation	+	0.5277	52.77%
Skin corrosion	-	0.8906	89.06%
Ames mutagenesis	-	0.9100	91.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5146	51.46%
Micronuclear	-	0.9400	94.00%
Hepatotoxicity	-	0.5250	52.50%
skin sensitisation	-	0.8106	81.06%
Respiratory toxicity	+	0.8000	80.00%
Reproductive toxicity	+	0.9889	98.89%
Mitochondrial toxicity	+	0.9375	93.75%
Nephrotoxicity	-	0.6927	69.27%
Acute Oral Toxicity (c)	III	0.7424	74.24%
Estrogen receptor binding	+	0.8075	80.75%
Androgen receptor binding	-	0.6706	67.06%
Thyroid receptor binding	+	0.6111	61.11%
Glucocorticoid receptor binding	+	0.8028	80.28%
Aromatase binding	-	0.7634	76.34%
PPAR gamma	-	0.4930	49.30%
Honey bee toxicity	-	0.9632	96.32%
Biodegradation	-	0.6000	60.00%
Crustacea aquatic toxicity	+	0.6065	60.65%
Fish aquatic toxicity	+	0.9893	98.93%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL6007	O75762	Transient receptor potential cation channel subfamily A member 1	15100 nM	EC50	PMID: 20356305

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL230	P35354	Cyclooxygenase-2	98.51%	89.63%
CHEMBL2581	P07339	Cathepsin D	98.40%	98.95%
CHEMBL3060	Q9Y345	Glycine transporter 2	97.22%	99.17%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	95.54%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	94.84%	96.09%
CHEMBL4769	O95749	Geranylgeranyl pyrophosphate synthetase	89.37%	92.08%
CHEMBL3359	P21462	Formyl peptide receptor 1	88.83%	93.56%
CHEMBL4227	P25090	Lipoxin A4 receptor	87.45%	100.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	87.32%	95.56%
CHEMBL2001	Q9H244	Purinergic receptor P2Y12	87.24%	96.00%
CHEMBL3401	O75469	Pregnane X receptor	85.66%	94.73%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	81.61%	90.71%
CHEMBL1781	P11387	DNA topoisomerase I	80.49%	97.00%
CHEMBL2274	Q9H228	Sphingosine 1-phosphate receptor Edg-8	80.43%	100.00%
CHEMBL340	P08684	Cytochrome P450 3A4	80.20%	91.19%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	80.06%	99.23%

Plants that contains it

• Larix sibirica

Cross-Links

• PubChem: 5281912
• NPASS: NPC192006
• ChEMBL: CHEMBL1084644
• LOTUS: LTS0245862
• wikiData: Q27098093