(4aS,6aR,6aS,6bR,8aR,9R,10S,12aS)-10-[(2R,3R,4S,5S,6R)-3,5-dihydroxy-6-methyl-4-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]oxy-4a,9-bis(hydroxymethyl)-2,2,6a,6b,9,12a-hexamethyl-3,4,6,6a,7,8,8a,10,11,12-decahydro-1H-picen-5-one

Details

• Internal ID: eaf69691-30d2-42b3-8d6a-a1c0174ac164
• Taxonomy: Lipids and lipid-like molecules > Steroids and steroid derivatives
• IUPAC Name: (4aS,6aR,6aS,6bR,8aR,9R,10S,12aS)-10-[(2R,3R,4S,5S,6R)-3,5-dihydroxy-6-methyl-4-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]oxy-4a,9-bis(hydroxymethyl)-2,2,6a,6b,9,12a-hexamethyl-3,4,6,6a,7,8,8a,10,11,12-decahydro-1H-picen-5-one
• SMILES (Canonical): CC1C(C(C(C(O1)OC2CCC3(C(C2(C)CO)CCC4(C3C=CC5=C6CC(CCC6(C(=O)CC54C)CO)(C)C)C)C)O)OC7C(C(C(C(O7)CO)O)O)O)O
• SMILES (Isomeric): C[C@@H]1[C@@H]([C@@H]([C@H]([C@@H](O1)O[C@H]2CC[C@]3([C@H]([C@]2(C)CO)CC[C@@]4([C@@H]3C=CC5=C6CC(CC[C@@]6(C(=O)C[C@]54C)CO)(C)C)C)C)O)O[C@H]7[C@@H]([C@H]([C@@H]([C@H](O7)CO)O)O)O)O
• InChI: InChI=1S/C42H66O13/c1-21-29(47)34(55-35-32(50)31(49)30(48)24(18-43)53-35)33(51)36(52-21)54-28-11-12-38(4)25(39(28,5)19-44)10-13-40(6)26(38)9-8-22-23-16-37(2,3)14-15-42(23,20-45)27(46)17-41(22,40)7/h8-9,21,24-26,28-36,43-45,47-51H,10-20H2,1-7H3/t21-,24-,25-,26-,28+,29+,30-,31+,32-,33-,34+,35+,36+,38+,39+,40-,41-,42-/m1/s1
• InChI Key: BWCBXZBZVSIHHX-VHHTULFKSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₄₂H₆₆O₁₃
• Molecular Weight: 779.00 g/mol
• Exact Mass: 778.45034216 g/mol
• Topological Polar Surface Area (TPSA): 216.00 Ų
• XlogP: 2.20
• Atomic LogP (AlogP): 1.89
• H-Bond Acceptor: 13
• H-Bond Donor: 8
• Rotatable Bonds: 7

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.7499	74.99%
Caco-2	-	0.8726	87.26%
Blood Brain Barrier	-	0.6750	67.50%
Human oral bioavailability	-	0.7429	74.29%
Subcellular localzation	Mitochondria	0.8758	87.58%
OATP2B1 inhibitior	-	0.8725	87.25%
OATP1B1 inhibitior	+	0.8286	82.86%
OATP1B3 inhibitior	-	0.5977	59.77%
MATE1 inhibitior	-	0.9812	98.12%
OCT2 inhibitior	-	0.5776	57.76%
BSEP inhibitior	+	0.7472	74.72%
P-glycoprotein inhibitior	+	0.7482	74.82%
P-glycoprotein substrate	-	0.5529	55.29%
CYP3A4 substrate	+	0.7256	72.56%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8698	86.98%
CYP3A4 inhibition	-	0.9589	95.89%
CYP2C9 inhibition	-	0.8763	87.63%
CYP2C19 inhibition	-	0.9003	90.03%
CYP2D6 inhibition	-	0.9427	94.27%
CYP1A2 inhibition	-	0.8671	86.71%
CYP2C8 inhibition	+	0.6209	62.09%
CYP inhibitory promiscuity	-	0.9423	94.23%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9700	97.00%
Carcinogenicity (trinary)	Non-required	0.6313	63.13%
Eye corrosion	-	0.9895	98.95%
Eye irritation	-	0.9122	91.22%
Skin irritation	-	0.6520	65.20%
Skin corrosion	-	0.9500	95.00%
Ames mutagenesis	-	0.7424	74.24%
Human Ether-a-go-go-Related Gene inhibition	+	0.7097	70.97%
Micronuclear	-	0.8700	87.00%
Hepatotoxicity	+	0.5573	55.73%
skin sensitisation	-	0.8940	89.40%
Respiratory toxicity	+	0.5667	56.67%
Reproductive toxicity	+	0.8667	86.67%
Mitochondrial toxicity	-	0.7750	77.50%
Nephrotoxicity	+	0.5459	54.59%
Acute Oral Toxicity (c)	III	0.7822	78.22%
Estrogen receptor binding	+	0.7596	75.96%
Androgen receptor binding	+	0.7384	73.84%
Thyroid receptor binding	-	0.5977	59.77%
Glucocorticoid receptor binding	+	0.6690	66.90%
Aromatase binding	+	0.6537	65.37%
PPAR gamma	+	0.7200	72.00%
Honey bee toxicity	-	0.7204	72.04%
Biodegradation	-	0.6750	67.50%
Crustacea aquatic toxicity	-	0.6450	64.50%
Fish aquatic toxicity	+	0.9603	96.03%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	98.34%	91.11%
CHEMBL1293249	Q13887	Kruppel-like factor 5	95.24%	86.33%
CHEMBL1937	Q92769	Histone deacetylase 2	94.97%	94.75%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	90.19%	94.00%
CHEMBL3137262	O60341	LSD1/CoREST complex	89.73%	97.09%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	89.44%	95.56%
CHEMBL3351	Q13085	Acetyl-CoA carboxylase 1	88.91%	93.04%
CHEMBL3714130	P46095	G-protein coupled receptor 6	88.04%	97.36%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	87.39%	96.09%
CHEMBL253	P34972	Cannabinoid CB2 receptor	87.34%	97.25%
CHEMBL1994	P08235	Mineralocorticoid receptor	86.66%	100.00%
CHEMBL2581	P07339	Cathepsin D	85.52%	98.95%
CHEMBL1907602	P06493	Cyclin-dependent kinase 1/cyclin B1	84.94%	91.24%
CHEMBL5608	Q16288	NT-3 growth factor receptor	84.07%	95.89%
CHEMBL2842	P42345	Serine/threonine-protein kinase mTOR	83.22%	92.78%
CHEMBL1806	P11388	DNA topoisomerase II alpha	82.80%	89.00%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	82.70%	94.45%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	81.07%	99.23%
CHEMBL4829	O00763	Acetyl-CoA carboxylase 2	80.34%	98.00%

Plants that contains it

• Bupleurum chinense

Cross-Links

• PubChem: 122189262
• LOTUS: LTS0145327
• wikiData: Q104947104