(2S,6S,9R,10S,11R,15S,20S,23R)-10-hydroxy-6,10,23-trimethyl-20-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-4-azahexacyclo[12.11.0.02,11.04,9.015,24.018,23]pentacosan-17-one

Details

• Internal ID: 4fcce4da-adcb-481c-8f4d-b96c22c0cd8e
• Taxonomy: Lipids and lipid-like molecules > Steroids and steroid derivatives > Steroidal glycosides > Steroidal saponins
• IUPAC Name: (2S,6S,9R,10S,11R,15S,20S,23R)-10-hydroxy-6,10,23-trimethyl-20-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-4-azahexacyclo[12.11.0.02,11.04,9.015,24.018,23]pentacosan-17-one
• SMILES (Canonical): CC1CCC2C(C3CCC4C(C3CN2C1)CC5C4CC(=O)C6C5(CCC(C6)OC7C(C(C(C(O7)CO)O)O)O)C)(C)O
• SMILES (Isomeric): C[C@H]1CC[C@@H]2[C@@]([C@@H]3CCC4[C@@H]5CC(=O)C6C[C@H](CC[C@@]6(C5CC4[C@@H]3CN2C1)C)O[C@H]7[C@@H]([C@H]([C@@H]([C@H](O7)CO)O)O)O)(C)O
• InChI: InChI=1S/C33H53NO8/c1-16-4-7-27-33(3,40)22-6-5-18-19(21(22)14-34(27)13-16)11-23-20(18)12-25(36)24-10-17(8-9-32(23,24)2)41-31-30(39)29(38)28(37)26(15-35)42-31/h16-24,26-31,35,37-40H,4-15H2,1-3H3/t16-,17-,18?,19?,20-,21-,22+,23?,24?,26+,27+,28+,29-,30+,31+,32+,33-/m0/s1
• InChI Key: DHQFYEJMFMYGCV-WHESZCKWSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₃₃H₅₃NO₈
• Molecular Weight: 591.80 g/mol
• Exact Mass: 591.37711765 g/mol
• Topological Polar Surface Area (TPSA): 140.00 Ų
• XlogP: 2.30
• Atomic LogP (AlogP): 1.71
• H-Bond Acceptor: 9
• H-Bond Donor: 5
• Rotatable Bonds: 3

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.7421	74.21%
Caco-2	-	0.8480	84.80%
Blood Brain Barrier	-	0.6000	60.00%
Human oral bioavailability	-	0.7714	77.14%
Subcellular localzation	Lysosomes	0.5438	54.38%
OATP2B1 inhibitior	-	0.5740	57.40%
OATP1B1 inhibitior	+	0.8807	88.07%
OATP1B3 inhibitior	+	0.9315	93.15%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.8000	80.00%
BSEP inhibitior	-	0.4584	45.84%
P-glycoprotein inhibitior	+	0.5801	58.01%
P-glycoprotein substrate	-	0.5659	56.59%
CYP3A4 substrate	+	0.7344	73.44%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8202	82.02%
CYP3A4 inhibition	-	0.8830	88.30%
CYP2C9 inhibition	-	0.9102	91.02%
CYP2C19 inhibition	-	0.9049	90.49%
CYP2D6 inhibition	-	0.9277	92.77%
CYP1A2 inhibition	-	0.9498	94.98%
CYP2C8 inhibition	-	0.5900	59.00%
CYP inhibitory promiscuity	-	0.9511	95.11%
UGT catelyzed	-	0.6000	60.00%
Carcinogenicity (binary)	-	0.9800	98.00%
Carcinogenicity (trinary)	Non-required	0.5496	54.96%
Eye corrosion	-	0.9884	98.84%
Eye irritation	-	0.9378	93.78%
Skin irritation	-	0.7642	76.42%
Skin corrosion	-	0.9402	94.02%
Ames mutagenesis	-	0.8004	80.04%
Human Ether-a-go-go-Related Gene inhibition	+	0.7107	71.07%
Micronuclear	+	0.5300	53.00%
Hepatotoxicity	-	0.6197	61.97%
skin sensitisation	-	0.8772	87.72%
Respiratory toxicity	+	0.7333	73.33%
Reproductive toxicity	+	0.8667	86.67%
Mitochondrial toxicity	+	0.9000	90.00%
Nephrotoxicity	+	0.4742	47.42%
Acute Oral Toxicity (c)	III	0.4864	48.64%
Estrogen receptor binding	+	0.6194	61.94%
Androgen receptor binding	+	0.7573	75.73%
Thyroid receptor binding	-	0.6194	61.94%
Glucocorticoid receptor binding	-	0.5000	50.00%
Aromatase binding	+	0.5866	58.66%
PPAR gamma	+	0.5357	53.57%
Honey bee toxicity	-	0.7283	72.83%
Biodegradation	-	0.6750	67.50%
Crustacea aquatic toxicity	+	0.5500	55.00%
Fish aquatic toxicity	-	0.5748	57.48%

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	97.96%	96.09%
CHEMBL253	P34972	Cannabinoid CB2 receptor	96.91%	97.25%
CHEMBL3137262	O60341	LSD1/CoREST complex	95.57%	97.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	94.80%	91.11%
CHEMBL1293249	Q13887	Kruppel-like factor 5	92.30%	86.33%
CHEMBL2581	P07339	Cathepsin D	91.14%	98.95%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	90.49%	96.77%
CHEMBL1994	P08235	Mineralocorticoid receptor	89.83%	100.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	88.32%	95.56%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	88.13%	94.45%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	87.92%	85.14%
CHEMBL3880	P07900	Heat shock protein HSP 90-alpha	87.91%	96.21%
CHEMBL1806	P11388	DNA topoisomerase II alpha	87.76%	89.00%
CHEMBL5608	Q16288	NT-3 growth factor receptor	87.72%	95.89%
CHEMBL5255	O00206	Toll-like receptor 4	87.21%	92.50%
CHEMBL5103	Q969S8	Histone deacetylase 10	85.51%	90.08%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	83.41%	94.00%
CHEMBL4681	P42330	Aldo-keto-reductase family 1 member C3	83.27%	89.05%
CHEMBL3351	Q13085	Acetyl-CoA carboxylase 1	83.23%	93.04%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	83.21%	95.89%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	83.20%	86.92%
CHEMBL325	Q13547	Histone deacetylase 1	82.59%	95.92%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	81.76%	97.14%
CHEMBL4187	Q99250	Sodium channel protein type II alpha subunit	80.49%	95.50%
CHEMBL1937	Q92769	Histone deacetylase 2	80.38%	94.75%

Plants that contains it

• Fritillaria monantha
• Humulus lupulus
• Leuzea carthamoides

Cross-Links

• PubChem: 6325353
• NPASS: NPC204050