[(2S,4R,5R,5aS,6S,8S,9R,9aR,10S,10aS)-6,10-diacetyloxy-2,4,8-trihydroxy-10a-(2-hydroxypropan-2-yl)-3,5a-dimethylspiro[2,4,5,6,7,8,9a,10-octahydro-1H-benzo[f]azulene-9,2'-oxirane]-5-yl] benzoate

Details

• Internal ID: 4320cc89-30ae-47fe-85a9-77ca1ca4082d
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Diterpenoids > Taxanes and derivatives
• IUPAC Name: [(2S,4R,5R,5aS,6S,8S,9R,9aR,10S,10aS)-6,10-diacetyloxy-2,4,8-trihydroxy-10a-(2-hydroxypropan-2-yl)-3,5a-dimethylspiro[2,4,5,6,7,8,9a,10-octahydro-1H-benzo[f]azulene-9,2'-oxirane]-5-yl] benzoate
• SMILES (Canonical): CC1=C2C(C(C3(C(CC(C4(C3C(C2(CC1O)C(C)(C)O)OC(=O)C)CO4)O)OC(=O)C)C)OC(=O)C5=CC=CC=C5)O
• SMILES (Isomeric): CC1=C2[C@H]([C@@H]([C@@]3([C@H](C[C@@H]([C@@]4([C@H]3[C@@H]([C@@]2(C[C@@H]1O)C(C)(C)O)OC(=O)C)CO4)O)OC(=O)C)C)OC(=O)C5=CC=CC=C5)O
• InChI: InChI=1S/C31H40O11/c1-15-19(34)13-30(28(4,5)38)22(15)23(36)25(42-27(37)18-10-8-7-9-11-18)29(6)21(40-16(2)32)12-20(35)31(14-39-31)24(29)26(30)41-17(3)33/h7-11,19-21,23-26,34-36,38H,12-14H2,1-6H3/t19-,20-,21-,23+,24-,25-,26-,29+,30-,31+/m0/s1
• InChI Key: VXDWKDPOYAZLDR-TWEGWBIASA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₃₁H₄₀O₁₁
• Molecular Weight: 588.60 g/mol
• Exact Mass: 588.25706209 g/mol
• Topological Polar Surface Area (TPSA): 172.00 Ų
• XlogP: 0.20
• Atomic LogP (AlogP): 1.44
• H-Bond Acceptor: 11
• H-Bond Donor: 4
• Rotatable Bonds: 5

Synonyms

• [(2S,4R,5R,5aS,6S,8S,9R,9aR,10S,10aS)-6,10-diacetyloxy-2,4,8-trihydroxy-10a-(2-hydroxypropan-2-yl)-3,5a-dimethylspiro[2,4,5,6,7,8,9a,10-octahydro-1H-benzo[f]azulene-9,2'-oxirane]-5-yl] benzoate
• VXDWKDPOYAZLDR-TWEGWBIASA-N
• (1S,4R)-4,20-Epoxy-1,11-cyclo-11,15-secotax-11-ene-2alpha,5alpha,7beta,9alpha,10beta,13alpha,15-heptol 2,7-diacetate 9-benzoate

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9882	98.82%
Caco-2	-	0.7702	77.02%
Blood Brain Barrier	+	0.6750	67.50%
Human oral bioavailability	-	0.6286	62.86%
Subcellular localzation	Mitochondria	0.7820	78.20%
OATP2B1 inhibitior	-	0.7170	71.70%
OATP1B1 inhibitior	+	0.8792	87.92%
OATP1B3 inhibitior	+	0.9177	91.77%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	-	0.8614	86.14%
BSEP inhibitior	+	0.8222	82.22%
P-glycoprotein inhibitior	+	0.7396	73.96%
P-glycoprotein substrate	+	0.5329	53.29%
CYP3A4 substrate	+	0.6719	67.19%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8589	85.89%
CYP3A4 inhibition	-	0.7376	73.76%
CYP2C9 inhibition	-	0.6266	62.66%
CYP2C19 inhibition	-	0.7539	75.39%
CYP2D6 inhibition	-	0.9087	90.87%
CYP1A2 inhibition	-	0.6631	66.31%
CYP2C8 inhibition	+	0.8095	80.95%
CYP inhibitory promiscuity	-	0.8658	86.58%
UGT catelyzed	-	0.6000	60.00%
Carcinogenicity (binary)	-	0.9600	96.00%
Carcinogenicity (trinary)	Non-required	0.5890	58.90%
Eye corrosion	-	0.9889	98.89%
Eye irritation	-	0.9032	90.32%
Skin irritation	-	0.6369	63.69%
Skin corrosion	-	0.9407	94.07%
Ames mutagenesis	-	0.6000	60.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.6938	69.38%
Micronuclear	-	0.5100	51.00%
Hepatotoxicity	+	0.5727	57.27%
skin sensitisation	-	0.7906	79.06%
Respiratory toxicity	+	0.6556	65.56%
Reproductive toxicity	+	0.9667	96.67%
Mitochondrial toxicity	+	0.8125	81.25%
Nephrotoxicity	+	0.6271	62.71%
Acute Oral Toxicity (c)	I	0.4248	42.48%
Estrogen receptor binding	+	0.7849	78.49%
Androgen receptor binding	+	0.6786	67.86%
Thyroid receptor binding	+	0.5386	53.86%
Glucocorticoid receptor binding	+	0.6760	67.60%
Aromatase binding	+	0.6945	69.45%
PPAR gamma	+	0.6835	68.35%
Honey bee toxicity	-	0.7506	75.06%
Biodegradation	-	0.8750	87.50%
Crustacea aquatic toxicity	-	0.5300	53.00%
Fish aquatic toxicity	+	0.9964	99.64%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL2581	P07339	Cathepsin D	96.62%	98.95%
CHEMBL1293249	Q13887	Kruppel-like factor 5	96.56%	86.33%
CHEMBL1951	P21397	Monoamine oxidase A	93.49%	91.49%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	93.01%	95.56%
CHEMBL1293277	O15118	Niemann-Pick C1 protein	92.56%	81.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	89.96%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	89.86%	91.11%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	89.38%	95.50%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	89.09%	97.14%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	88.15%	99.23%
CHEMBL5028	O14672	ADAM10	87.32%	97.50%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	86.39%	91.07%
CHEMBL2035	P08912	Muscarinic acetylcholine receptor M5	86.09%	94.62%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	85.43%	96.95%
CHEMBL3137262	O60341	LSD1/CoREST complex	83.53%	97.09%
CHEMBL3401	O75469	Pregnane X receptor	81.45%	94.73%
CHEMBL1806	P11388	DNA topoisomerase II alpha	81.40%	89.00%
CHEMBL5608	Q16288	NT-3 growth factor receptor	81.40%	95.89%
CHEMBL3475	P05121	Plasminogen activator inhibitor-1	81.13%	83.00%
CHEMBL340	P08684	Cytochrome P450 3A4	80.32%	91.19%
CHEMBL5966	P55899	IgG receptor FcRn large subunit p51	80.14%	90.93%

Plants that contains it

• Equisetum hyemale
• Taxus mairei

Cross-Links

• PubChem: 15385644
• NPASS: NPC110114
• LOTUS: LTS0107336
• wikiData: Q105298450