[(4R)-4-[(1'R,2'R,3R,3aR,4R,4'R,7aS,8'S,12'S,15'S)-15'-acetyloxy-4-hydroxy-2',6,11'-trimethyl-7'-methylidene-2,6'-dioxospiro[3a,4,7,7a-tetrahydro-1-benzofuran-3,13'-5-oxatetracyclo[10.2.1.01,10.04,8]pentadec-10-ene]-5-yl]pentyl] acetate

Details

• Internal ID: d757c058-020b-48c1-9565-bbfc369bd34c
• Taxonomy: Lipids and lipid-like molecules > Fatty Acyls > Eicosanoids > Prostaglandins and related compounds
• IUPAC Name: [(4R)-4-[(1'R,2'R,3R,3aR,4R,4'R,7aS,8'S,12'S,15'S)-15'-acetyloxy-4-hydroxy-2',6,11'-trimethyl-7'-methylidene-2,6'-dioxospiro[3a,4,7,7a-tetrahydro-1-benzofuran-3,13'-5-oxatetracyclo[10.2.1.01,10.04,8]pentadec-10-ene]-5-yl]pentyl] acetate
• SMILES (Canonical): CC1CC2C(CC3=C(C4C(C13CC45C6C(CC(=C(C6O)C(C)CCCOC(=O)C)C)OC5=O)OC(=O)C)C)C(=C)C(=O)O2
• SMILES (Isomeric): C[C@@H]1C[C@@H]2[C@@H](CC3=C([C@@H]4[C@@H]([C@]13C[C@]45[C@H]6[C@H](CC(=C([C@@H]6O)[C@H](C)CCCOC(=O)C)C)OC5=O)OC(=O)C)C)C(=C)C(=O)O2
• InChI: InChI=1S/C34H44O9/c1-15(9-8-10-40-20(6)35)26-16(2)11-25-28(29(26)37)34(32(39)43-25)14-33-17(3)12-24-22(18(4)31(38)42-24)13-23(33)19(5)27(34)30(33)41-21(7)36/h15,17,22,24-25,27-30,37H,4,8-14H2,1-3,5-7H3/t15-,17-,22+,24-,25+,27-,28+,29+,30+,33-,34-/m1/s1
• InChI Key: FPZMKWNKHQRDMW-RSQKRGDPSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₃₄H₄₄O₉
• Molecular Weight: 596.70 g/mol
• Exact Mass: 596.29853298 g/mol
• Topological Polar Surface Area (TPSA): 125.00 Ų
• XlogP: 2.60
• Atomic LogP (AlogP): 4.37
• H-Bond Acceptor: 9
• H-Bond Donor: 1
• Rotatable Bonds: 6

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9810	98.10%
Caco-2	-	0.8036	80.36%
Blood Brain Barrier	+	0.8250	82.50%
Human oral bioavailability	-	0.5429	54.29%
Subcellular localzation	Mitochondria	0.8095	80.95%
OATP2B1 inhibitior	-	0.7152	71.52%
OATP1B1 inhibitior	+	0.8472	84.72%
OATP1B3 inhibitior	+	0.8777	87.77%
MATE1 inhibitior	-	0.9000	90.00%
OCT2 inhibitior	+	0.5479	54.79%
BSEP inhibitior	+	0.7903	79.03%
P-glycoprotein inhibitior	+	0.7838	78.38%
P-glycoprotein substrate	+	0.6688	66.88%
CYP3A4 substrate	+	0.7120	71.20%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8776	87.76%
CYP3A4 inhibition	-	0.7122	71.22%
CYP2C9 inhibition	-	0.7553	75.53%
CYP2C19 inhibition	-	0.8777	87.77%
CYP2D6 inhibition	-	0.9487	94.87%
CYP1A2 inhibition	-	0.6235	62.35%
CYP2C8 inhibition	+	0.6568	65.68%
CYP inhibitory promiscuity	-	0.8594	85.94%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9700	97.00%
Carcinogenicity (trinary)	Non-required	0.4943	49.43%
Eye corrosion	-	0.9889	98.89%
Eye irritation	-	0.9114	91.14%
Skin irritation	+	0.5939	59.39%
Skin corrosion	-	0.9269	92.69%
Ames mutagenesis	-	0.5000	50.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.6488	64.88%
Micronuclear	-	0.7600	76.00%
Hepatotoxicity	+	0.7020	70.20%
skin sensitisation	-	0.8838	88.38%
Respiratory toxicity	+	0.6444	64.44%
Reproductive toxicity	+	0.9778	97.78%
Mitochondrial toxicity	+	0.6500	65.00%
Nephrotoxicity	+	0.8870	88.70%
Acute Oral Toxicity (c)	III	0.5717	57.17%
Estrogen receptor binding	+	0.7855	78.55%
Androgen receptor binding	+	0.7276	72.76%
Thyroid receptor binding	-	0.5660	56.60%
Glucocorticoid receptor binding	+	0.7927	79.27%
Aromatase binding	+	0.7347	73.47%
PPAR gamma	+	0.6657	66.57%
Honey bee toxicity	-	0.6493	64.93%
Biodegradation	-	0.7500	75.00%
Crustacea aquatic toxicity	-	0.5600	56.00%
Fish aquatic toxicity	+	1.0000	100.00%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL2996	Q05655	Protein kinase C delta	98.76%	97.79%
CHEMBL253	P34972	Cannabinoid CB2 receptor	98.73%	97.25%
CHEMBL299	P17252	Protein kinase C alpha	97.32%	98.03%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	96.68%	96.09%
CHEMBL2581	P07339	Cathepsin D	95.57%	98.95%
CHEMBL3145	P42338	PI3-kinase p110-beta subunit	93.87%	98.75%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	93.47%	91.11%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	93.39%	94.45%
CHEMBL335	P18031	Protein-tyrosine phosphatase 1B	91.76%	95.17%
CHEMBL3130	O00329	PI3-kinase p110-delta subunit	91.73%	96.47%
CHEMBL5103	Q969S8	Histone deacetylase 10	91.15%	90.08%
CHEMBL3807	P17706	T-cell protein-tyrosine phosphatase	89.99%	93.00%
CHEMBL3137262	O60341	LSD1/CoREST complex	89.76%	97.09%
CHEMBL3359	P21462	Formyl peptide receptor 1	88.93%	93.56%
CHEMBL1907602	P06493	Cyclin-dependent kinase 1/cyclin B1	88.77%	91.24%
CHEMBL1293249	Q13887	Kruppel-like factor 5	87.42%	86.33%
CHEMBL3975	P09467	Fructose-1,6-bisphosphatase	87.30%	92.95%
CHEMBL3267	P48736	PI3-kinase p110-gamma subunit	86.90%	95.71%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	85.22%	95.50%
CHEMBL4657	Q6V1X1	Dipeptidyl peptidase VIII	85.15%	97.21%
CHEMBL3437	Q16853	Amine oxidase, copper containing	84.80%	94.00%
CHEMBL1902	P62942	FK506-binding protein 1A	83.55%	97.05%
CHEMBL3060	Q9Y345	Glycine transporter 2	83.37%	99.17%
CHEMBL1806	P11388	DNA topoisomerase II alpha	83.14%	89.00%
CHEMBL5608	Q16288	NT-3 growth factor receptor	82.53%	95.89%
CHEMBL3045	P05771	Protein kinase C beta	82.22%	97.63%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	81.72%	85.14%
CHEMBL5163	Q9NY46	Sodium channel protein type III alpha subunit	80.96%	96.90%

Plants that contains it

• Pentanema britannicum

Cross-Links

• PubChem: 162940737
• LOTUS: LTS0252392
• wikiData: Q104999492