prostaglandin B2

Details

• Internal ID: f3e24aa0-1b33-4662-a242-f521df1299cb
• Taxonomy: Lipids and lipid-like molecules > Fatty Acyls > Eicosanoids > Prostaglandins and related compounds
• IUPAC Name: (Z)-7-[2-[(E,3S)-3-hydroxyoct-1-enyl]-5-oxocyclopenten-1-yl]hept-5-enoic acid
• SMILES (Canonical): CCCCCC(C=CC1=C(C(=O)CC1)CC=CCCCC(=O)O)O
• SMILES (Isomeric): CCCCC[C@@H](/C=C/C1=C(C(=O)CC1)C/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/h4,7,12,14,17,21H,2-3,5-6,8-11,13,15H2,1H3,(H,23,24)/b7-4-,14-12+/t17-/m0/s1
• InChI Key: PRFXRIUZNKLRHM-HKVRTXJWSA-N
• Popularity: 35 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: 3.30
• Atomic LogP (AlogP): 4.34
• H-Bond Acceptor: 3
• H-Bond Donor: 2
• Rotatable Bonds: 12

Synonyms

• 13367-85-6
• PGB2
• UNII-BIU61O9T9T
• PGB2 (Prostaglandin B2)
• BIU61O9T9T
• CHEBI:28099
• (Z)-7-[2-[(E,3S)-3-hydroxyoct-1-enyl]-5-oxocyclopenten-1-yl]hept-5-enoic acid
• 15S-hydroxy-9-oxo-5Z,8(12),13E-prostatrienoic acid
• Prosta-5,8(12),13-trien-1-oic acid, 15-hydroxy-9-oxo-, (5Z,13E,15S)-
• Prosta-5,8(12),13-trien-1-oicacid, 15-hydroxy-9-oxo-, (5Z,13E,15S)-
• prosta-glandinb2
• BSPBio_001484
• PGB2-[d4]
• BML1-F04
• SCHEMBL3368055
• CHEMBL1901620
• BCBcMAP01_000173
• DTXSID50864391
• PRFXRIUZNKLRHM-HKVRTXJWSA-N
• HMS1361K06
• HMS1791K06
• HMS1989K06
• HMS3402K06
• HMS3648K17
• LMFA03010018
• (5Z,13E,15S)-15-hydroxy-9-oxoprosta-5,8(12),13-trien-1-oic acid
• AKOS040755329
• Prostaglandin B2, >=98%, synthetic
• DB02304
• IDI1_033954
• NCGC00161283-01
• NCGC00161283-02
• NCGC00161283-03
• HY-113042
• CS-0059421
• DINOPROSTONE IMPURITY E [EP IMPURITY]
• C05954
• SR-01000946234
• J-006426
• SR-01000946234-1
• BRD-K82865713-001-02-6
• Q27093323
• 15-HYDROXY-9-OXOPROSTA-5,8(12),13-TRIENOIC ACID
• 15.ALPHA.-HYDROXY-9-KETOPROSTA-5,8(12),13-TRIENOIC ACID
• (5Z,13E,15S)-15-HYDROXY-9-OXOPROSTA-5, 8(12),13-TRIEN-1-OIC ACID
• (Z)-7-(2-((E)-(3S)-3-HYDROXYOCT-1-ENYL)-5-OXOCYCLOPENT-1-ENYL)HEPT-5-ENOIC ACID
• (Z)-7-[2-[(E,3R)-3-hydroxyoct-1-enyl]-5-oxocyclopenten-1-yl]hept-5-enoic acid
• DINOPROSTONE IMPURITY, (5Z,13E,15S)-15-HYDROXY-9-OXOPROSTA-5, 8(12),13-TRIEN-1-OIC ACID- [USP IMPURITY]

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9785	97.85%
Caco-2	-	0.6566	65.66%
Blood Brain Barrier	-	0.8250	82.50%
Human oral bioavailability	-	0.7000	70.00%
Subcellular localzation	Mitochondria	0.8378	83.78%
OATP2B1 inhibitior	-	0.8550	85.50%
OATP1B1 inhibitior	+	0.7674	76.74%
OATP1B3 inhibitior	+	0.9469	94.69%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	-	0.7570	75.70%
BSEP inhibitior	+	0.6148	61.48%
P-glycoprotein inhibitior	-	0.6968	69.68%
P-glycoprotein substrate	-	0.8001	80.01%
CYP3A4 substrate	+	0.5367	53.67%
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	-	0.8154	81.54%
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	-	0.7721	77.21%
Skin irritation	+	0.4893	48.93%
Skin corrosion	-	0.9277	92.77%
Ames mutagenesis	-	0.8637	86.37%
Human Ether-a-go-go-Related Gene inhibition	+	0.6718	67.18%
Micronuclear	-	0.8900	89.00%
Hepatotoxicity	-	0.6446	64.46%
skin sensitisation	-	0.7478	74.78%
Respiratory toxicity	+	0.6778	67.78%
Reproductive toxicity	+	0.9111	91.11%
Mitochondrial toxicity	+	0.8750	87.50%
Nephrotoxicity	-	0.8349	83.49%
Acute Oral Toxicity (c)	III	0.6061	60.61%
Estrogen receptor binding	+	0.7802	78.02%
Androgen receptor binding	-	0.5666	56.66%
Thyroid receptor binding	+	0.5146	51.46%
Glucocorticoid receptor binding	+	0.8371	83.71%
Aromatase binding	-	0.6902	69.02%
PPAR gamma	+	0.7889	78.89%
Honey bee toxicity	-	0.9685	96.85%
Biodegradation	-	0.6500	65.00%
Crustacea aquatic toxicity	+	0.5600	56.00%
Fish aquatic toxicity	+	0.9922	99.22%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL2581	P07339	Cathepsin D	98.65%	98.95%
CHEMBL3060	Q9Y345	Glycine transporter 2	97.41%	99.17%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	93.94%	96.09%
CHEMBL230	P35354	Cyclooxygenase-2	92.88%	89.63%
CHEMBL1781	P11387	DNA topoisomerase I	91.72%	97.00%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	91.66%	91.11%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	90.38%	85.14%
CHEMBL4227	P25090	Lipoxin A4 receptor	90.19%	100.00%
CHEMBL2001	Q9H244	Purinergic receptor P2Y12	89.92%	96.00%
CHEMBL4769	O95749	Geranylgeranyl pyrophosphate synthetase	88.83%	92.08%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	88.44%	95.56%
CHEMBL3359	P21462	Formyl peptide receptor 1	88.07%	93.56%
CHEMBL2274	Q9H228	Sphingosine 1-phosphate receptor Edg-8	82.77%	100.00%
CHEMBL221	P23219	Cyclooxygenase-1	82.75%	90.17%
CHEMBL253	P34972	Cannabinoid CB2 receptor	82.40%	97.25%
CHEMBL3807	P17706	T-cell protein-tyrosine phosphatase	81.38%	93.00%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	80.52%	90.71%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	80.22%	96.00%

Plants that contains it

• Acanthosyris spinescens
• Agrimonia eupatoria
• Alluaudia humbertii
• Alstonia lanceolifera
• Campanula medium
• Echinops spinosissimus
• Eruca vesicaria
• Euphorbia nivulia
• Gleditsia triacanthos
• Hedyotis lawsoniae
• Hemionitis tenuifolia
• Humboldtia laurifolia
• Hyalosperma glutinosum
• Ilex macropoda
• Larix sibirica
• Lycium cestroides
• Lycopodiella cernua
• Magnolia salicifolia
• Paepalanthus hilairei
• Pieris formosa
• Pterocaulon alopecuroides
• Rhabdodendron amazonicum
• Selaginella uncinata
• Senna siamea
• Seriphidium caerulescens subsp. caerulescens
• Sloanea zuliaensis
• Tetracera rosiflora
• Teucrium montanum
• Tillandsia fragrans
• Uvariopsis tripetala

Cross-Links

• PubChem: 5280881
• NPASS: NPC236208
• LOTUS: LTS0067136
• wikiData: Q27093323