[(1S,4R,12R,16S,17S)-17-hydroxy-12-methyl-8-oxapentacyclo[14.2.1.01,13.04,12.05,9]nonadeca-5(9),6,10-trien-17-yl]methyl (Z)-octadec-9-enoate

Details

• Internal ID: bb36b75c-b16e-4557-9379-bda30418ff12
• Taxonomy: Organoheterocyclic compounds > Naphthofurans
• IUPAC Name: [(1S,4R,12R,16S,17S)-17-hydroxy-12-methyl-8-oxapentacyclo[14.2.1.01,13.04,12.05,9]nonadeca-5(9),6,10-trien-17-yl]methyl (Z)-octadec-9-enoate
• SMILES (Canonical): CCCCCCCCC=CCCCCCCCC(=O)OCC1(CC23CCC4C5=C(C=CC4(C2CCC1C3)C)OC=C5)O
• SMILES (Isomeric): CCCCCCCC/C=C\CCCCCCCC(=O)OC[C@@]1(C[C@@]23CC[C@H]4C5=C(C=C[C@@]4(C2CC[C@H]1C3)C)OC=C5)O
• InChI: InChI=1S/C38H58O4/c1-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-35(39)42-29-38(40)28-37-25-21-32-31-23-26-41-33(31)22-24-36(32,2)34(37)20-19-30(38)27-37/h10-11,22-24,26,30,32,34,40H,3-9,12-21,25,27-29H2,1-2H3/b11-10-/t30-,32-,34?,36-,37-,38+/m0/s1
• InChI Key: MDXDAWWJXQHCAA-QLMAWPHDSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₃₈H₅₈O₄
• Molecular Weight: 578.90 g/mol
• Exact Mass: 578.43351033 g/mol
• Topological Polar Surface Area (TPSA): 59.70 Ų
• XlogP: 11.50
• Atomic LogP (AlogP): 10.31
• H-Bond Acceptor: 4
• H-Bond Donor: 1
• Rotatable Bonds: 17

Synonyms

• 108214-30-8

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9963	99.63%
Caco-2	-	0.8038	80.38%
Blood Brain Barrier	+	0.6000	60.00%
Human oral bioavailability	-	0.6000	60.00%
Subcellular localzation	Mitochondria	0.7514	75.14%
OATP2B1 inhibitior	-	0.8576	85.76%
OATP1B1 inhibitior	+	0.8106	81.06%
OATP1B3 inhibitior	+	0.9472	94.72%
MATE1 inhibitior	-	0.9000	90.00%
OCT2 inhibitior	-	0.7750	77.50%
BSEP inhibitior	+	0.9327	93.27%
P-glycoprotein inhibitior	+	0.6883	68.83%
P-glycoprotein substrate	+	0.5960	59.60%
CYP3A4 substrate	+	0.7138	71.38%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8624	86.24%
CYP3A4 inhibition	+	0.5237	52.37%
CYP2C9 inhibition	-	0.5773	57.73%
CYP2C19 inhibition	+	0.5223	52.23%
CYP2D6 inhibition	-	0.8862	88.62%
CYP1A2 inhibition	-	0.7193	71.93%
CYP2C8 inhibition	+	0.7759	77.59%
CYP inhibitory promiscuity	-	0.6084	60.84%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9400	94.00%
Carcinogenicity (trinary)	Non-required	0.6497	64.97%
Eye corrosion	-	0.9925	99.25%
Eye irritation	-	0.9313	93.13%
Skin irritation	-	0.6564	65.64%
Skin corrosion	-	0.9502	95.02%
Ames mutagenesis	-	0.9432	94.32%
Human Ether-a-go-go-Related Gene inhibition	-	0.4762	47.62%
Micronuclear	-	0.8600	86.00%
Hepatotoxicity	-	0.7250	72.50%
skin sensitisation	-	0.8617	86.17%
Respiratory toxicity	+	0.6667	66.67%
Reproductive toxicity	+	0.8222	82.22%
Mitochondrial toxicity	+	0.8250	82.50%
Nephrotoxicity	-	0.8829	88.29%
Acute Oral Toxicity (c)	III	0.4887	48.87%
Estrogen receptor binding	+	0.8994	89.94%
Androgen receptor binding	+	0.7044	70.44%
Thyroid receptor binding	-	0.5767	57.67%
Glucocorticoid receptor binding	+	0.6994	69.94%
Aromatase binding	+	0.5568	55.68%
PPAR gamma	+	0.5638	56.38%
Honey bee toxicity	-	0.8566	85.66%
Biodegradation	-	0.7500	75.00%
Crustacea aquatic toxicity	+	0.8653	86.53%
Fish aquatic toxicity	+	0.9954	99.54%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL240	Q12809	HERG	99.86%	89.76%
CHEMBL3060	Q9Y345	Glycine transporter 2	97.95%	99.17%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	97.89%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	96.79%	96.09%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	94.36%	94.45%
CHEMBL2581	P07339	Cathepsin D	94.33%	98.95%
CHEMBL253	P34972	Cannabinoid CB2 receptor	92.78%	97.25%
CHEMBL221	P23219	Cyclooxygenase-1	91.45%	90.17%
CHEMBL2274	Q9H228	Sphingosine 1-phosphate receptor Edg-8	91.11%	100.00%
CHEMBL4227	P25090	Lipoxin A4 receptor	91.01%	100.00%
CHEMBL3137262	O60341	LSD1/CoREST complex	90.37%	97.09%
CHEMBL1293249	Q13887	Kruppel-like factor 5	88.62%	86.33%
CHEMBL5608	Q16288	NT-3 growth factor receptor	88.47%	95.89%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	88.04%	92.62%
CHEMBL2955	O95136	Sphingosine 1-phosphate receptor Edg-5	87.94%	92.86%
CHEMBL5255	O00206	Toll-like receptor 4	87.87%	92.50%
CHEMBL3359	P21462	Formyl peptide receptor 1	85.95%	93.56%
CHEMBL4685	P14902	Indoleamine 2,3-dioxygenase	85.54%	96.38%
CHEMBL4187	Q99250	Sodium channel protein type II alpha subunit	83.53%	95.50%
CHEMBL3430907	Q96GD4	Aurora kinase B/Inner centromere protein	83.50%	97.50%
CHEMBL2996	Q05655	Protein kinase C delta	82.88%	97.79%
CHEMBL2001	Q9H244	Purinergic receptor P2Y12	82.71%	96.00%
CHEMBL1806	P11388	DNA topoisomerase II alpha	81.64%	89.00%
CHEMBL3891	P07384	Calpain 1	80.55%	93.04%
CHEMBL4481	P35228	Nitric oxide synthase, inducible	80.26%	94.80%

Plants that contains it

• Coffea arabica

Cross-Links

• PubChem: 137699546
• LOTUS: LTS0246617
• wikiData: Q104393996