Prostaglandin B1

Details

• Internal ID: 0ce1df4a-d0e2-4bd4-a7c0-522affc39fec
• Taxonomy: Lipids and lipid-like molecules > Fatty Acyls > Eicosanoids > Prostaglandins and related compounds
• IUPAC Name: 7-[2-[(E,3S)-3-hydroxyoct-1-enyl]-5-oxocyclopenten-1-yl]heptanoic acid
• SMILES (Canonical): CCCCCC(C=CC1=C(C(=O)CC1)CCCCCCC(=O)O)O
• SMILES (Isomeric): CCCCC[C@@H](/C=C/C1=C(C(=O)CC1)CCCCCCC(=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/h12,14,17,21H,2-11,13,15H2,1H3,(H,23,24)/b14-12+/t17-/m0/s1
• InChI Key: YBHMPNRDOVPQIN-VSOYFRJCSA-N
• Popularity: 32 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: 4.00
• Atomic LogP (AlogP): 4.57
• H-Bond Acceptor: 3
• H-Bond Donor: 2
• Rotatable Bonds: 13

Synonyms

• PGB1
• 13345-51-2
• Prostaglandin Bx
• PROSTAGLANDINB1
• 39306-29-1
• UNII-1TYI1PJ64T
• PGB1 (Prostaglandin B1)
• 1TYI1PJ64T
• MLS000069509
• CHEMBL1561148
• CHEBI:27624
• (13E,15S)-15-hydroxy-9-oxoprosta-8(12),13-dien-1-oic acid
• 7-[2-[(E,3S)-3-hydroxyoct-1-enyl]-5-oxocyclopenten-1-yl]heptanoic acid
• Prosta-8(12),13-dien-1-oic acid, 15-hydroxy-9-oxo-, (13E,15S)-
• 9-oxo-15S-hydroxy-8(12),13E-prostadienoic acid
• SMR000058636
• Prosta-8(12),13-dien-1-oicacid, 15-hydroxy-9-oxo-, (13E,15S)-
• 15(S)-hydroxy-9-oxo-8(12),13-trans-prostadienoic acid
• Prostaglandin E1-278
• SR-01000000044
• PGE1-278
• Prostaglandin-B1
• PGBx
• (13E,15S)-15-hydroxy-9-oxoprosta-8(12),13-dien-1-oate
• starbld0016672
• Opera_ID_1128
• BSPBio_001482
• BML1-F03
• SCHEMBL9576915
• SCHEMBL9576919
• YBHMPNRDOVPQIN-VSOYFRJCSA-N
• DTXSID001347609
• HMS1361K04
• HMS1791K04
• HMS1989K04
• HMS2233A12
• HMS3402K04
• HMS3648K15
• PROSTAGLANDIN B1 [USP-RS]
• Prostaglandin B1, synthetic, powder
• BDBM50390997
• LMFA03010131
• CCG-208254
• IDI1_033952
• NCGC00024019-03
• NCGC00024019-04
• NCGC00024019-05
• ALPROSTADIL IMPURITY B [EP IMPURITY]
• 9-oxo-15S-hydroxy-8(12),13E-prostadienoate
• C00959
• J-006385
• SR-01000000044-4
• SR-01000000044-5
• SR-01000000044-6
• Q27103232
• 15.ALPHA.-HYDROXY-9-KETOPROSTA-8(12),13-DIENOIC ACID
• 15.ALPHA.-HYDROXY-9-OXO-8(12),13E-PROSTADIENOIC ACID
• Prosta-8(12),13-dien-1-oicacid,15-hydroxy-9-oxo-,(13E,15S)-
• (S,E)-7-(2-(3-hydroxyoct-1-enyl)-5-oxocyclopent-1-enyl)heptanoic acid
• 7-[2-[(E,3S)-3-hydroxyoct-1-enyl]-5-oxo-cyclopenten-1-yl]heptanoic acid
• Prostaglandin B1, United States Pharmacopeia (USP) Reference Standard
• 7-(2-((1E,3S)-3-HYDROXYOCT-1-ENYL)-5-OXOCYCLOPENT-1-ENYL)HEPTANOIC ACID

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9785	97.85%
Caco-2	-	0.5565	55.65%
Blood Brain Barrier	-	0.8250	82.50%
Human oral bioavailability	-	0.8143	81.43%
Subcellular localzation	Mitochondria	0.8378	83.78%
OATP2B1 inhibitior	-	0.8546	85.46%
OATP1B1 inhibitior	+	0.8796	87.96%
OATP1B3 inhibitior	+	0.9469	94.69%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	-	0.7570	75.70%
BSEP inhibitior	+	0.5764	57.64%
P-glycoprotein inhibitior	-	0.6888	68.88%
P-glycoprotein substrate	-	0.7762	77.62%
CYP3A4 substrate	+	0.5391	53.91%
CYP2C9 substrate	-	0.5973	59.73%
CYP2D6 substrate	-	0.8947	89.47%
CYP3A4 inhibition	-	0.8899	88.99%
CYP2C9 inhibition	-	0.9419	94.19%
CYP2C19 inhibition	-	0.8904	89.04%
CYP2D6 inhibition	-	0.8552	85.52%
CYP1A2 inhibition	-	0.9098	90.98%
CYP2C8 inhibition	-	0.8341	83.41%
CYP inhibitory promiscuity	-	0.9385	93.85%
UGT catelyzed	-	0.7000	70.00%
Carcinogenicity (binary)	-	0.9300	93.00%
Carcinogenicity (trinary)	Non-required	0.7021	70.21%
Eye corrosion	-	0.9926	99.26%
Eye irritation	-	0.6298	62.98%
Skin irritation	+	0.4893	48.93%
Skin corrosion	-	0.9277	92.77%
Ames mutagenesis	-	0.9237	92.37%
Human Ether-a-go-go-Related Gene inhibition	+	0.6490	64.90%
Micronuclear	-	0.8900	89.00%
Hepatotoxicity	-	0.5250	52.50%
skin sensitisation	-	0.7478	74.78%
Respiratory toxicity	+	0.6889	68.89%
Reproductive toxicity	+	0.9111	91.11%
Mitochondrial toxicity	+	0.8750	87.50%
Nephrotoxicity	-	0.7551	75.51%
Acute Oral Toxicity (c)	III	0.6061	60.61%
Estrogen receptor binding	+	0.7583	75.83%
Androgen receptor binding	-	0.5751	57.51%
Thyroid receptor binding	+	0.6244	62.44%
Glucocorticoid receptor binding	+	0.7919	79.19%
Aromatase binding	-	0.8121	81.21%
PPAR gamma	+	0.7647	76.47%
Honey bee toxicity	-	0.9764	97.64%
Biodegradation	+	0.5250	52.50%
Crustacea aquatic toxicity	+	0.6065	60.65%
Fish aquatic toxicity	+	0.9922	99.22%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL3577	P00352	Aldehyde dehydrogenase 1A1	31622.8 nM	Potency	via CMAUP
CHEMBL1293236	P46063	ATP-dependent DNA helicase Q1	10000 nM	Potency	via CMAUP
CHEMBL2392	P06746	DNA polymerase beta	22387.2 nM	Potency	via CMAUP
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	100 nM; 100 nM; 100 nM	Potency; Potency; Potency	via CMAUP; via CMAUP; via Super-PRED
CHEMBL1293235	P02545	Prelamin-A/C	2511.9 nM	Potency	via CMAUP

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL2581	P07339	Cathepsin D	98.98%	98.95%
CHEMBL230	P35354	Cyclooxygenase-2	98.67%	89.63%
CHEMBL3060	Q9Y345	Glycine transporter 2	96.99%	99.17%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	95.47%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	94.37%	91.11%
CHEMBL4769	O95749	Geranylgeranyl pyrophosphate synthetase	91.73%	92.08%
CHEMBL2001	Q9H244	Purinergic receptor P2Y12	89.88%	96.00%
CHEMBL2274	Q9H228	Sphingosine 1-phosphate receptor Edg-8	88.78%	100.00%
CHEMBL4227	P25090	Lipoxin A4 receptor	88.31%	100.00%
CHEMBL3359	P21462	Formyl peptide receptor 1	87.74%	93.56%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	87.11%	95.56%
CHEMBL253	P34972	Cannabinoid CB2 receptor	83.35%	97.25%
CHEMBL1781	P11387	DNA topoisomerase I	82.81%	97.00%
CHEMBL5805	Q9NR97	Toll-like receptor 8	81.50%	96.25%
CHEMBL335	P18031	Protein-tyrosine phosphatase 1B	81.26%	95.17%
CHEMBL3130	O00329	PI3-kinase p110-delta subunit	81.23%	96.47%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	81.18%	90.71%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	80.92%	99.23%
CHEMBL5255	O00206	Toll-like receptor 4	80.31%	92.50%
CHEMBL3892	Q99500	Sphingosine 1-phosphate receptor Edg-3	80.20%	97.29%
CHEMBL3392948	Q9NP59	Solute carrier family 40 member 1	80.19%	95.00%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	80.09%	96.00%

Plants that contains it

• Larix sibirica

Cross-Links

• PubChem: 5280388
• NPASS: NPC227396
• ChEMBL: CHEMBL1561148
• LOTUS: LTS0233157
• wikiData: Q27103232