prostaglandin A2

Details

• Internal ID: a052ce99-cd66-4dd7-b29d-f2ee3ebf0a21
• Taxonomy: Lipids and lipid-like molecules > Fatty Acyls > Eicosanoids > Prostaglandins and related compounds
• IUPAC Name: (Z)-7-[(1R,2S)-2-[(E,3S)-3-hydroxyoct-1-enyl]-5-oxocyclopent-3-en-1-yl]hept-5-enoic acid
• SMILES (Canonical): CCCCCC(C=CC1C=CC(=O)C1CC=CCCCC(=O)O)O
• SMILES (Isomeric): CCCCC[C@@H](/C=C/[C@H]1C=CC(=O)[C@@H]1C/C=C\CCCC(=O)O)O
• InChI: 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/h4,7,12-18,21H,2-3,5-6,8-11H2,1H3,(H,23,24)/b7-4-,14-12+/t16-,17-,18+/m0/s1
• InChI Key: MYHXHCUNDDAEOZ-FOSBLDSVSA-N
• Popularity: 179 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₀H₃₀O₄
• Molecular Weight: 334.40 g/mol
• Exact Mass: 334.21440943 g/mol
• Topological Polar Surface Area (TPSA): 74.60 Ų
• XlogP: 3.60
• Atomic LogP (AlogP): 4.06
• H-Bond Acceptor: 3
• H-Bond Donor: 2
• Rotatable Bonds: 12

Synonyms

• Medullin
• PGA2
• 13345-50-1
• (+)-Prostaglandin A2
• 5,6-cis-PGA2
• (15S)-PGA2
• (+)-Prostaglandin A(sup 2)
• K6VT5BDY9E
• 15(S)-Prostaglandin A2
• CHEBI:27820
• Prosta-5,10,13-trien-1-oic acid, 15-hydroxy-9-oxo-, (5Z,13E,15S)-
• 9-oxo-15S-hydroxy-5Z,10Z,13E-prostatrienoic acid
• (Z)-7-[(1R,2S)-2-[(E,3S)-3-hydroxyoct-1-enyl]-5-oxocyclopent-3-en-1-yl]hept-5-enoic acid
• 15(S)-Hydroxy-9-oxo-5-cis-10,13-trans-prostatrienoic acid
• Prosta-5,10,13-trien-1-oicacid, 15-hydroxy-9-oxo-, (5Z,13E,15S)-
• NSC 165561
• PGA2 (Prostaglandin A2)
• 15(S)-Hydroxy-9-oxo-5-cis-10,13-trans-prostenoic acid
• PGA(sup 2)
• 5,6-cis-PGA(sup 2)
• MLS000069589
• Prostaglandin A(sup 2)
• UNII-K6VT5BDY9E
• (155)-PGA2
• BRN 2221844
• NSC-165561
• PGA2;Medullin
• (~{Z})-7-[(1~{R},5~{S})-2-oxidanylidene-5-[(~{E},3~{S})-3-oxidanyloct-1-enyl]cyclopent-3-en-1-yl]hept-5-enoic acid
• SMR000058790
• Pga2(prostaglandin a2)
• BSPBio_001460
• BML1-F02
• GTPL6279
• SCHEMBL2115595
• CHEMBL1084643
• DTXSID20864388
• PROSTAGLANDIN A2 (PGA2)
• HMS1361I22
• HMS1791I22
• HMS1989I22
• HMS3402I22
• HMS3648I11
• (5Z,13E,15S)-15-hydroxy-9-oxoprosta-5, 10,13-triene-1-oic acid
• (5Z,13E,15S)-15-hydroxy-9-oxoprosta-5,10,13-trien-1-oic acid
• LMFA03010035
• AKOS040755328
• Prosta-5,10-13-trien-1-oic acid, 15-hydroxy-9-oxo-, (5Z,13E,15S)-
• (Z)-7-((1R,2S)-2-((E)-(3S)-3-hydroxyoct-1-enyl)-5-oxocyclopent-3-enyl)hept-5-enoic acid
• 5-Heptenoic acid, 7-(2-(3-hydroxy-1-octenyl)-5-oxo-3-cyclopenten-1-yl)- (VAN)
• IDI1_033930
• NCGC00022061-03
• NCGC00022061-04
• NCGC00022061-05
• HY-113041
• CS-0059420
• DINOPROSTONE IMPURITY D [EP IMPURITY]
• C05953
• SR-01000946222
• SR-01000946222-1
• 15(S)-Hydroxy-9-oxo-5-cis-10,13-trans-prostenoate
• BRD-K34782918-001-02-5
• Q27088462
• 15a-Hydroxy-9-oxo-cis-5,10,trans-13-prostatrienoate
• 15(S)-Hydroxy-9-oxo-5-cis-10,13-trans-prostatrienoate
• 15a-Hydroxy-9-oxo-cis-5,10,trans-13-prostatrienoic acid
• 15a-Hydroxy-9-oxo-cis-5,10,trans-13-prostatrienecarboxylate
• 362927F3-3A3E-47BC-84C3-C32A293AA956
• 15.alpha.-Hydroxy-9-oxo-cis-5,10,trans-13-prostatrienoic acid
• 15a-Hydroxy-9-oxo-cis-5,10,trans-13-prostatrienecarboxylic acid
• 15.alpha.-Hydroxy-9-oxo-cis-5,10,trans-13-prostatrienecarboxylic acid
• (Z)-7-[(1R,2S)-2-[(E,3S)-3-hydroxyoct-1-enyl]-5-oxo-1-cyclopent-3-enyl]hept-5-enoic acid
• (Z)-7-[(1R,2S)-2-[(E,3S)-3-hydroxyoct-1-enyl]-5-oxo-cyclopent-3-en-1-yl]hept-5-enoic acid
• DINOPROSTONE IMPURITY, (5Z,13E,15S)-15-HYDROXY-9-OXOPROSTA-5, 10,13-TRIENE-1-OIC ACID- [USP IMPURITY]

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9711	97.11%
Caco-2	-	0.6839	68.39%
Blood Brain Barrier	-	0.8500	85.00%
Human oral bioavailability	-	0.7429	74.29%
Subcellular localzation	Mitochondria	0.8450	84.50%
OATP2B1 inhibitior	-	0.8559	85.59%
OATP1B1 inhibitior	-	0.3550	35.50%
OATP1B3 inhibitior	+	0.9399	93.99%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.9000	90.00%
BSEP inhibitior	-	0.5155	51.55%
P-glycoprotein inhibitior	-	0.7709	77.09%
P-glycoprotein substrate	-	0.7257	72.57%
CYP3A4 substrate	+	0.5497	54.97%
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	-	0.7963	79.63%
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	-	0.9400	94.00%
Skin irritation	+	0.5277	52.77%
Skin corrosion	-	0.8906	89.06%
Ames mutagenesis	-	0.8954	89.54%
Human Ether-a-go-go-Related Gene inhibition	-	0.4830	48.30%
Micronuclear	-	0.9400	94.00%
Hepatotoxicity	-	0.5875	58.75%
skin sensitisation	-	0.8106	81.06%
Respiratory toxicity	+	0.8444	84.44%
Reproductive toxicity	+	0.9889	98.89%
Mitochondrial toxicity	+	0.9375	93.75%
Nephrotoxicity	-	0.7820	78.20%
Acute Oral Toxicity (c)	III	0.7424	74.24%
Estrogen receptor binding	+	0.7769	77.69%
Androgen receptor binding	-	0.5857	58.57%
Thyroid receptor binding	-	0.5531	55.31%
Glucocorticoid receptor binding	+	0.8781	87.81%
Aromatase binding	-	0.7090	70.90%
PPAR gamma	+	0.6020	60.20%
Honey bee toxicity	-	0.9547	95.47%
Biodegradation	-	0.7000	70.00%
Crustacea aquatic toxicity	+	0.5500	55.00%
Fish aquatic toxicity	+	0.9893	98.93%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL1293235	P02545	Prelamin-A/C	7.9 nM	Potency	via Super-PRED

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL2581	P07339	Cathepsin D	98.17%	98.95%
CHEMBL3060	Q9Y345	Glycine transporter 2	97.58%	99.17%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	95.17%	91.11%
CHEMBL230	P35354	Cyclooxygenase-2	94.26%	89.63%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	90.98%	96.09%
CHEMBL253	P34972	Cannabinoid CB2 receptor	90.27%	97.25%
CHEMBL1781	P11387	DNA topoisomerase I	89.48%	97.00%
CHEMBL2001	Q9H244	Purinergic receptor P2Y12	88.27%	96.00%
CHEMBL3401	O75469	Pregnane X receptor	88.21%	94.73%
CHEMBL4769	O95749	Geranylgeranyl pyrophosphate synthetase	86.59%	92.08%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	86.59%	95.56%
CHEMBL3359	P21462	Formyl peptide receptor 1	85.52%	93.56%
CHEMBL4227	P25090	Lipoxin A4 receptor	84.29%	100.00%
CHEMBL1881	P43116	Prostanoid EP2 receptor	80.81%	93.00%

Plants that contains it

• Larix sibirica

Cross-Links

• PubChem: 5280880
• LOTUS: LTS0104516
• wikiData: Q27088462