(3beta,16beta,23R)-16,23:16,30-Diepoxy-20-hydroxydammar-24-en-3-yl O-6-deoxy-alpha-L-mannopyranosyl-(1-->2)-O-[O-beta-D-xylopyranosyl-(1-->2)-6-O-acetyl-beta-D-glucopyranosyl-(1-->3)]-alpha-L-arabinopyranoside

Details

• Internal ID: 6a7bbcfa-d605-4353-accf-0f3c966807b5
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Triterpenoids
• IUPAC Name: [(2R,3S,4S,5R,6S)-3,4-dihydroxy-6-[(2S,3R,4S,5S)-5-hydroxy-2-[[(1S,2R,5R,7S,10R,11R,14R,15S,16S,18R,20S)-16-hydroxy-2,6,6,10,16-pentamethyl-18-(2-methylprop-1-enyl)-19,21-dioxahexacyclo[18.2.1.01,14.02,11.05,10.015,20]tricosan-7-yl]oxy]-3-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyoxan-4-yl]oxy-5-[(2S,3R,4S,5R)-3,4,5-trihydroxyoxan-2-yl]oxyoxan-2-yl]methyl acetate
• SMILES (Canonical): CC1C(C(C(C(O1)OC2C(C(COC2OC3CCC4(C5CCC6C7C(CC(OC78CC6(C5(CCC4C3(C)C)C)CO8)C=C(C)C)(C)O)C)O)OC9C(C(C(C(O9)COC(=O)C)O)O)OC1C(C(C(CO1)O)O)O)O)O)O
• SMILES (Isomeric): C[C@H]1[C@@H]([C@H]([C@H]([C@@H](O1)O[C@@H]2[C@H]([C@H](CO[C@H]2O[C@H]3CC[C@@]4([C@H]5CC[C@@H]6[C@H]7[C@@](C[C@@H](O[C@@]78C[C@]6([C@@]5(CC[C@H]4C3(C)C)C)CO8)C=C(C)C)(C)O)C)O)O[C@H]9[C@@H]([C@H]([C@@H]([C@H](O9)COC(=O)C)O)O)O[C@H]1[C@@H]([C@H]([C@@H](CO1)O)O)O)O)O)O
• InChI: InChI=1S/C54H86O22/c1-23(2)16-26-17-52(9,65)44-27-10-11-32-50(7)14-13-33(49(5,6)31(50)12-15-51(32,8)53(27)21-54(44,76-26)69-22-53)72-47-43(75-46-40(64)37(61)34(58)24(3)70-46)41(29(57)19-68-47)73-48-42(74-45-39(63)35(59)28(56)18-67-45)38(62)36(60)30(71-48)20-66-25(4)55/h16,24,26-48,56-65H,10-15,17-22H2,1-9H3/t24-,26-,27+,28+,29-,30+,31-,32+,33-,34-,35-,36+,37+,38-,39+,40+,41-,42+,43+,44-,45-,46-,47-,48-,50-,51+,52-,53-,54-/m0/s1
• InChI Key: JCNHTOHJIDUGID-MDSFCDLTSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₅₄H₈₆O₂₂
• Molecular Weight: 1087.20 g/mol
• Exact Mass: 1086.56107437 g/mol
• Topological Polar Surface Area (TPSA): 321.00 Ų
• XlogP: 0.60
• Atomic LogP (AlogP): 0.03
• H-Bond Acceptor: 22
• H-Bond Donor: 10
• Rotatable Bonds: 11

Synonyms

• (3beta,16beta,23R)-16,23:16,30-Diepoxy-20-hydroxydammar-24-en-3-yl O-6-deoxy-alpha-L-mannopyranosyl-(1-->2)-O-[O-beta-D-xylopyranosyl-(1-->2)-6-O-acetyl-beta-D-glucopyranosyl-(1-->3)]-alpha-L-arabinopyranoside
• 194737-13-8

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.8513	85.13%
Caco-2	-	0.8813	88.13%
Blood Brain Barrier	-	0.6750	67.50%
Human oral bioavailability	-	0.7286	72.86%
Subcellular localzation	Mitochondria	0.8366	83.66%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8187	81.87%
OATP1B3 inhibitior	+	0.8847	88.47%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.7250	72.50%
BSEP inhibitior	+	0.9369	93.69%
P-glycoprotein inhibitior	+	0.7485	74.85%
P-glycoprotein substrate	+	0.6387	63.87%
CYP3A4 substrate	+	0.7583	75.83%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8831	88.31%
CYP3A4 inhibition	-	0.9302	93.02%
CYP2C9 inhibition	-	0.8485	84.85%
CYP2C19 inhibition	-	0.8883	88.83%
CYP2D6 inhibition	-	0.9267	92.67%
CYP1A2 inhibition	-	0.9043	90.43%
CYP2C8 inhibition	+	0.7697	76.97%
CYP inhibitory promiscuity	-	0.9304	93.04%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.5735	57.35%
Eye corrosion	-	0.9908	99.08%
Eye irritation	-	0.9015	90.15%
Skin irritation	+	0.4909	49.09%
Skin corrosion	-	0.9417	94.17%
Ames mutagenesis	-	0.5300	53.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7829	78.29%
Micronuclear	-	0.8700	87.00%
Hepatotoxicity	-	0.8125	81.25%
skin sensitisation	-	0.8889	88.89%
Respiratory toxicity	+	0.7222	72.22%
Reproductive toxicity	+	0.8667	86.67%
Mitochondrial toxicity	+	0.5125	51.25%
Nephrotoxicity	-	0.9227	92.27%
Acute Oral Toxicity (c)	I	0.5916	59.16%
Estrogen receptor binding	+	0.8015	80.15%
Androgen receptor binding	+	0.7545	75.45%
Thyroid receptor binding	+	0.5398	53.98%
Glucocorticoid receptor binding	+	0.7741	77.41%
Aromatase binding	+	0.6674	66.74%
PPAR gamma	+	0.8131	81.31%
Honey bee toxicity	-	0.5911	59.11%
Biodegradation	-	0.7250	72.50%
Crustacea aquatic toxicity	+	0.5545	55.45%
Fish aquatic toxicity	+	0.9728	97.28%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL253	P34972	Cannabinoid CB2 receptor	98.28%	97.25%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	98.11%	96.09%
CHEMBL218	P21554	Cannabinoid CB1 receptor	96.26%	96.61%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	95.27%	91.11%
CHEMBL325	Q13547	Histone deacetylase 1	94.90%	95.92%
CHEMBL221	P23219	Cyclooxygenase-1	93.26%	90.17%
CHEMBL226	P30542	Adenosine A1 receptor	93.00%	95.93%
CHEMBL2581	P07339	Cathepsin D	92.52%	98.95%
CHEMBL1806	P11388	DNA topoisomerase II alpha	91.29%	89.00%
CHEMBL1937	Q92769	Histone deacetylase 2	91.18%	94.75%
CHEMBL4681	P42330	Aldo-keto-reductase family 1 member C3	89.87%	89.05%
CHEMBL1907602	P06493	Cyclin-dependent kinase 1/cyclin B1	89.70%	91.24%
CHEMBL3145	P42338	PI3-kinase p110-beta subunit	88.89%	98.75%
CHEMBL2179	P04062	Beta-glucocerebrosidase	88.30%	85.31%
CHEMBL1994	P08235	Mineralocorticoid receptor	87.82%	100.00%
CHEMBL3137262	O60341	LSD1/CoREST complex	87.77%	97.09%
CHEMBL1293249	Q13887	Kruppel-like factor 5	87.55%	86.33%
CHEMBL5255	O00206	Toll-like receptor 4	87.46%	92.50%
CHEMBL3267	P48736	PI3-kinase p110-gamma subunit	87.22%	95.71%
CHEMBL4187	Q99250	Sodium channel protein type II alpha subunit	86.84%	95.50%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	86.50%	95.89%
CHEMBL3714130	P46095	G-protein coupled receptor 6	86.47%	97.36%
CHEMBL340	P08684	Cytochrome P450 3A4	85.64%	91.19%
CHEMBL1163125	O60885	Bromodomain-containing protein 4	84.89%	97.31%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	84.52%	82.69%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	83.93%	95.56%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	83.76%	96.95%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	83.63%	94.45%
CHEMBL3922	P50579	Methionine aminopeptidase 2	83.00%	97.28%
CHEMBL5028	O14672	ADAM10	82.43%	97.50%
CHEMBL5957	P21589	5'-nucleotidase	82.22%	97.78%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	82.19%	94.33%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	82.08%	92.62%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	82.08%	96.77%
CHEMBL5888	Q99558	Mitogen-activated protein kinase kinase kinase 14	81.48%	100.00%
CHEMBL5608	Q16288	NT-3 growth factor receptor	81.41%	95.89%
CHEMBL2274	Q9H228	Sphingosine 1-phosphate receptor Edg-8	81.30%	100.00%
CHEMBL3807	P17706	T-cell protein-tyrosine phosphatase	81.23%	93.00%
CHEMBL241	Q14432	Phosphodiesterase 3A	80.79%	92.94%
CHEMBL4005	P42336	PI3-kinase p110-alpha subunit	80.66%	97.47%

Plants that contains it

• Ziziphus jujuba

Cross-Links

• PubChem: 101709345
• LOTUS: LTS0120313
• wikiData: Q105124991