[(1S,3R,4R,5R,6S,10S,12S,16R,18S,21R)-4,6,12,17,17-pentamethyl-8-(2-methylpropanoyl)-18-[(2S,3R,4S,5R)-3,4,5-trihydroxyoxan-2-yl]oxy-9-oxahexacyclo[11.9.0.01,21.04,12.05,10.016,21]docosa-7,13-dien-3-yl] acetate

Details

• Internal ID: fc4d68c8-d11a-4eb5-9325-9546193d67ae
• Taxonomy: Lipids and lipid-like molecules > Steroids and steroid derivatives > Cycloartanols and derivatives
• IUPAC Name: [(1S,3R,4R,5R,6S,10S,12S,16R,18S,21R)-4,6,12,17,17-pentamethyl-8-(2-methylpropanoyl)-18-[(2S,3R,4S,5R)-3,4,5-trihydroxyoxan-2-yl]oxy-9-oxahexacyclo[11.9.0.01,21.04,12.05,10.016,21]docosa-7,13-dien-3-yl] acetate
• SMILES (Canonical): CC1C=C(OC2C1C3(C(CC45CC46CCC(C(C6CC=C5C3(C2)C)(C)C)OC7C(C(C(CO7)O)O)O)OC(=O)C)C)C(=O)C(C)C
• SMILES (Isomeric): C[C@@H]1C=C(O[C@@H]2[C@H]1[C@]3([C@@H](C[C@@]45C[C@@]46CC[C@@H](C([C@@H]6CC=C5[C@@]3(C2)C)(C)C)O[C@H]7[C@@H]([C@H]([C@@H](CO7)O)O)O)OC(=O)C)C)C(=O)C(C)C
• InChI: InChI=1S/C37H54O9/c1-18(2)29(40)22-13-19(3)28-23(45-22)14-34(7)25-10-9-24-33(5,6)26(46-32-31(42)30(41)21(39)16-43-32)11-12-36(24)17-37(25,36)15-27(35(28,34)8)44-20(4)38/h10,13,18-19,21,23-24,26-28,30-32,39,41-42H,9,11-12,14-17H2,1-8H3/t19-,21-,23+,24+,26+,27-,28+,30+,31-,32+,34+,35-,36-,37+/m1/s1
• InChI Key: OICQARGRQPYOBP-CTECLONPSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₃₇H₅₄O₉
• Molecular Weight: 642.80 g/mol
• Exact Mass: 642.37678330 g/mol
• Topological Polar Surface Area (TPSA): 132.00 Ų
• XlogP: 4.60
• Atomic LogP (AlogP): 4.47
• H-Bond Acceptor: 9
• H-Bond Donor: 3
• Rotatable Bonds: 5

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9057	90.57%
Caco-2	-	0.8418	84.18%
Blood Brain Barrier	-	0.6000	60.00%
Human oral bioavailability	-	0.6000	60.00%
Subcellular localzation	Mitochondria	0.8314	83.14%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8031	80.31%
OATP1B3 inhibitior	+	0.9068	90.68%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	-	0.6808	68.08%
BSEP inhibitior	+	0.7922	79.22%
P-glycoprotein inhibitior	+	0.7917	79.17%
P-glycoprotein substrate	+	0.6108	61.08%
CYP3A4 substrate	+	0.7333	73.33%
CYP2C9 substrate	-	0.8000	80.00%
CYP2D6 substrate	-	0.8902	89.02%
CYP3A4 inhibition	-	0.8807	88.07%
CYP2C9 inhibition	-	0.6985	69.85%
CYP2C19 inhibition	-	0.9099	90.99%
CYP2D6 inhibition	-	0.9382	93.82%
CYP1A2 inhibition	-	0.8655	86.55%
CYP2C8 inhibition	+	0.6565	65.65%
CYP inhibitory promiscuity	-	0.9563	95.63%
UGT catelyzed	-	0.6000	60.00%
Carcinogenicity (binary)	-	0.9500	95.00%
Carcinogenicity (trinary)	Non-required	0.6016	60.16%
Eye corrosion	-	0.9887	98.87%
Eye irritation	-	0.9225	92.25%
Skin irritation	-	0.5339	53.39%
Skin corrosion	-	0.9300	93.00%
Ames mutagenesis	-	0.6200	62.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7206	72.06%
Micronuclear	-	0.6800	68.00%
Hepatotoxicity	-	0.6375	63.75%
skin sensitisation	-	0.8677	86.77%
Respiratory toxicity	-	0.5000	50.00%
Reproductive toxicity	+	0.9667	96.67%
Mitochondrial toxicity	+	0.7125	71.25%
Nephrotoxicity	-	0.6358	63.58%
Acute Oral Toxicity (c)	III	0.4601	46.01%
Estrogen receptor binding	+	0.6951	69.51%
Androgen receptor binding	+	0.7376	73.76%
Thyroid receptor binding	-	0.5190	51.90%
Glucocorticoid receptor binding	+	0.7446	74.46%
Aromatase binding	+	0.7076	70.76%
PPAR gamma	+	0.7187	71.87%
Honey bee toxicity	-	0.6613	66.13%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	-	0.5100	51.00%
Fish aquatic toxicity	+	0.9844	98.44%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	98.63%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	96.18%	91.11%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	95.86%	96.77%
CHEMBL3145	P42338	PI3-kinase p110-beta subunit	94.41%	98.75%
CHEMBL2581	P07339	Cathepsin D	91.81%	98.95%
CHEMBL253	P34972	Cannabinoid CB2 receptor	91.54%	97.25%
CHEMBL1994	P08235	Mineralocorticoid receptor	88.48%	100.00%
CHEMBL1806	P11388	DNA topoisomerase II alpha	88.42%	89.00%
CHEMBL4685	P14902	Indoleamine 2,3-dioxygenase	88.14%	96.38%
CHEMBL3130	O00329	PI3-kinase p110-delta subunit	88.06%	96.47%
CHEMBL4225	P49760	Dual specificity protein kinase CLK2	87.19%	80.96%
CHEMBL340	P08684	Cytochrome P450 3A4	87.12%	91.19%
CHEMBL5608	Q16288	NT-3 growth factor receptor	86.76%	95.89%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	86.14%	97.14%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	86.12%	82.69%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	85.61%	94.45%
CHEMBL3267	P48736	PI3-kinase p110-gamma subunit	83.97%	95.71%
CHEMBL3137262	O60341	LSD1/CoREST complex	83.75%	97.09%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	83.31%	92.62%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	82.23%	99.23%
CHEMBL4051	P13569	Cystic fibrosis transmembrane conductance regulator	81.83%	95.71%
CHEMBL2413	P32246	C-C chemokine receptor type 1	81.64%	89.50%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	81.61%	95.89%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	81.37%	91.07%
CHEMBL1937	Q92769	Histone deacetylase 2	80.98%	94.75%
CHEMBL1907602	P06493	Cyclin-dependent kinase 1/cyclin B1	80.78%	91.24%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	80.30%	95.56%
CHEMBL1293249	Q13887	Kruppel-like factor 5	80.06%	86.33%

Plants that contains it

• Actaea asiatica
• Centella asiatica

Cross-Links

• PubChem: 16091660
• NPASS: NPC133506
• ChEMBL: CHEMBL449193
• LOTUS: LTS0027981
• wikiData: Q105192447