(20S)-3beta-(2-O-alpha-L-Rhamnopyranosyl-3-O-beta-D-xylopyranosyl-beta-D-glucopyranosyloxy)-21-(beta-D-glucopyranosyloxy)dammara-24-ene-19,20-diol

Details

• Internal ID: 9ea43cba-f38f-4201-bc0d-8a0d339104a7
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene glycosides > Triterpene glycosides > Triterpene saponins
• IUPAC Name: (2S,3R,4R,5R,6S)-2-[(2R,3R,4S,5R,6R)-5-hydroxy-6-(hydroxymethyl)-2-[[(3S,5R,8R,9S,10S,13R,14R,17S)-10-(hydroxymethyl)-17-[(2S)-2-hydroxy-6-methyl-1-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyhept-5-en-2-yl]-4,4,8,14-tetramethyl-2,3,5,6,7,9,11,12,13,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-yl]oxy]-4-[(2S,3R,4S,5R)-3,4,5-trihydroxyoxan-2-yl]oxyoxan-3-yl]oxy-6-methyloxane-3,4,5-triol
• SMILES (Canonical): CC1C(C(C(C(O1)OC2C(C(C(OC2OC3CCC4(C5CCC6C(CCC6(C5(CCC4C3(C)C)C)C)C(CCC=C(C)C)(COC7C(C(C(C(O7)CO)O)O)O)O)CO)CO)O)OC8C(C(C(CO8)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]([C@H](O[C@H]2O[C@H]3CC[C@@]4([C@H]5CC[C@@H]6[C@H](CC[C@]6([C@@]5(CC[C@H]4C3(C)C)C)C)[C@@](CCC=C(C)C)(CO[C@H]7[C@@H]([C@H]([C@@H]([C@H](O7)CO)O)O)O)O)CO)CO)O)O[C@H]8[C@@H]([C@H]([C@@H](CO8)O)O)O)O)O)O
• InChI: InChI=1S/C53H90O22/c1-24(2)9-8-15-53(67,23-69-46-41(65)39(63)36(60)29(19-54)71-46)27-12-16-50(6)26(27)10-11-32-51(50,7)17-13-31-49(4,5)33(14-18-52(31,32)22-56)73-48-44(75-47-42(66)38(62)34(58)25(3)70-47)43(37(61)30(20-55)72-48)74-45-40(64)35(59)28(57)21-68-45/h9,25-48,54-67H,8,10-23H2,1-7H3/t25-,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+/m0/s1
• InChI Key: KACVVWZFKSGSLO-GIVFAMPTSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₅₃H₉₀O₂₂
• Molecular Weight: 1079.30 g/mol
• Exact Mass: 1078.59237449 g/mol
• Topological Polar Surface Area (TPSA): 357.00 Ų
• XlogP: 0.50
• Atomic LogP (AlogP): -1.56
• H-Bond Acceptor: 22
• H-Bond Donor: 14
• Rotatable Bonds: 16

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.6877	68.77%
Caco-2	-	0.8964	89.64%
Blood Brain Barrier	-	0.5500	55.00%
Human oral bioavailability	-	0.7714	77.14%
Subcellular localzation	Mitochondria	0.7251	72.51%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8090	80.90%
OATP1B3 inhibitior	+	0.8189	81.89%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.6000	60.00%
BSEP inhibitior	+	0.9231	92.31%
P-glycoprotein inhibitior	+	0.7495	74.95%
P-glycoprotein substrate	+	0.5226	52.26%
CYP3A4 substrate	+	0.7323	73.23%
CYP2C9 substrate	-	0.7890	78.90%
CYP2D6 substrate	-	0.8406	84.06%
CYP3A4 inhibition	-	0.9502	95.02%
CYP2C9 inhibition	-	0.8671	86.71%
CYP2C19 inhibition	-	0.9036	90.36%
CYP2D6 inhibition	-	0.9380	93.80%
CYP1A2 inhibition	-	0.9057	90.57%
CYP2C8 inhibition	+	0.7713	77.13%
CYP inhibitory promiscuity	-	0.9413	94.13%
UGT catelyzed	-	0.7000	70.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.6474	64.74%
Eye corrosion	-	0.9907	99.07%
Eye irritation	-	0.9025	90.25%
Skin irritation	-	0.5956	59.56%
Skin corrosion	-	0.9488	94.88%
Ames mutagenesis	-	0.5500	55.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.8213	82.13%
Micronuclear	-	0.8800	88.00%
Hepatotoxicity	-	0.6609	66.09%
skin sensitisation	-	0.8991	89.91%
Respiratory toxicity	+	0.5556	55.56%
Reproductive toxicity	+	0.8889	88.89%
Mitochondrial toxicity	-	0.5875	58.75%
Nephrotoxicity	-	0.7766	77.66%
Acute Oral Toxicity (c)	I	0.5677	56.77%
Estrogen receptor binding	+	0.7854	78.54%
Androgen receptor binding	+	0.7526	75.26%
Thyroid receptor binding	-	0.5086	50.86%
Glucocorticoid receptor binding	+	0.7273	72.73%
Aromatase binding	+	0.6482	64.82%
PPAR gamma	+	0.8012	80.12%
Honey bee toxicity	-	0.5689	56.89%
Biodegradation	-	0.7500	75.00%
Crustacea aquatic toxicity	-	0.5100	51.00%
Fish aquatic toxicity	+	0.9172	91.72%

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	98.39%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	94.17%	96.09%
CHEMBL218	P21554	Cannabinoid CB1 receptor	92.42%	96.61%
CHEMBL1293249	Q13887	Kruppel-like factor 5	92.02%	86.33%
CHEMBL241	Q14432	Phosphodiesterase 3A	91.90%	92.94%
CHEMBL253	P34972	Cannabinoid CB2 receptor	91.38%	97.25%
CHEMBL226	P30542	Adenosine A1 receptor	91.09%	95.93%
CHEMBL3137262	O60341	LSD1/CoREST complex	90.92%	97.09%
CHEMBL1907602	P06493	Cyclin-dependent kinase 1/cyclin B1	90.73%	91.24%
CHEMBL1937	Q92769	Histone deacetylase 2	88.69%	94.75%
CHEMBL5608	Q16288	NT-3 growth factor receptor	88.54%	95.89%
CHEMBL3714130	P46095	G-protein coupled receptor 6	87.94%	97.36%
CHEMBL1907605	P24864	Cyclin-dependent kinase 2/cyclin E1	87.93%	92.88%
CHEMBL5888	Q99558	Mitogen-activated protein kinase kinase kinase 14	87.88%	100.00%
CHEMBL1994	P08235	Mineralocorticoid receptor	87.64%	100.00%
CHEMBL1951	P21397	Monoamine oxidase A	87.06%	91.49%
CHEMBL3589	P55263	Adenosine kinase	84.59%	98.05%
CHEMBL2274	Q9H228	Sphingosine 1-phosphate receptor Edg-8	84.56%	100.00%
CHEMBL2581	P07339	Cathepsin D	84.44%	98.95%
CHEMBL233	P35372	Mu opioid receptor	83.92%	97.93%
CHEMBL4187	Q99250	Sodium channel protein type II alpha subunit	83.62%	95.50%
CHEMBL3476	O15111	Inhibitor of nuclear factor kappa B kinase alpha subunit	83.09%	95.83%
CHEMBL325	Q13547	Histone deacetylase 1	81.34%	95.92%
CHEMBL2842	P42345	Serine/threonine-protein kinase mTOR	80.86%	92.78%
CHEMBL3060	Q9Y345	Glycine transporter 2	80.56%	99.17%
CHEMBL259	P32245	Melanocortin receptor 4	80.47%	95.38%
CHEMBL1806	P11388	DNA topoisomerase II alpha	80.45%	89.00%

Plants that contains it

• Coleostephus myconis
• Dahlia pinnata
• Gynostemma pentaphyllum
• Synotis alata

Cross-Links

• PubChem: 21579920
• NPASS: NPC307910
• LOTUS: LTS0176465
• wikiData: Q105137799