(20R,23R)-3beta-[[2-O-(alpha-L-Rhamnopyranosyl)-3-O-(beta-D-xylopyranosyl)-alpha-L-arabinopyranosyl]oxy]-20,23-dihydroxydammara-24-ene-21-oic acid 21,23-lactone

Details

• Internal ID: efbe3137-2337-494f-ad4e-49595a98ea19
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Triterpenoids
• IUPAC Name: (3R,5R)-3-hydroxy-3-[(3S,5R,8R,9R,10R,13R,14R,17S)-3-[(2S,3R,4S,5S)-5-hydroxy-3-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy-4-[(2S,3R,4S,5R)-3,4,5-trihydroxyoxan-2-yl]oxyoxan-2-yl]oxy-4,4,8,10,14-pentamethyl-2,3,5,6,7,9,11,12,13,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-17-yl]-5-(2-methylprop-1-enyl)oxolan-2-one
• SMILES (Canonical): CC1C(C(C(C(O1)OC2C(C(COC2OC3CCC4(C5CCC6C(CCC6(C5(CCC4C3(C)C)C)C)C7(CC(OC7=O)C=C(C)C)O)C)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](CO[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@@]7(C[C@@H](OC7=O)C=C(C)C)O)C)O)O[C@H]8[C@@H]([C@H]([C@@H](CO8)O)O)O)O)O)O
• InChI: InChI=1S/C46H74O16/c1-21(2)17-23-18-46(55,41(54)59-23)25-11-15-44(7)24(25)9-10-29-43(6)14-13-30(42(4,5)28(43)12-16-45(29,44)8)60-40-37(62-39-35(53)33(51)31(49)22(3)58-39)36(27(48)20-57-40)61-38-34(52)32(50)26(47)19-56-38/h17,22-40,47-53,55H,9-16,18-20H2,1-8H3/t22-,23-,24+,25-,26+,27-,28-,29+,30-,31-,32-,33+,34+,35+,36-,37+,38-,39-,40-,43-,44+,45+,46+/m0/s1
• InChI Key: QQZPCWCERZJGPZ-HAEOUJFESA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₄₆H₇₄O₁₆
• Molecular Weight: 883.10 g/mol
• Exact Mass: 882.49768627 g/mol
• Topological Polar Surface Area (TPSA): 244.00 Ų
• XlogP: 3.30
• Atomic LogP (AlogP): 1.82
• H-Bond Acceptor: 16
• H-Bond Donor: 8
• Rotatable Bonds: 8

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9035	90.35%
Caco-2	-	0.8858	88.58%
Blood Brain Barrier	-	0.8750	87.50%
Human oral bioavailability	-	0.7857	78.57%
Subcellular localzation	Mitochondria	0.8511	85.11%
OATP2B1 inhibitior	-	0.8787	87.87%
OATP1B1 inhibitior	+	0.8429	84.29%
OATP1B3 inhibitior	+	0.9216	92.16%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.9500	95.00%
BSEP inhibitior	+	0.7485	74.85%
P-glycoprotein inhibitior	+	0.7613	76.13%
P-glycoprotein substrate	+	0.5285	52.85%
CYP3A4 substrate	+	0.7494	74.94%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8719	87.19%
CYP3A4 inhibition	-	0.9299	92.99%
CYP2C9 inhibition	-	0.8711	87.11%
CYP2C19 inhibition	-	0.8985	89.85%
CYP2D6 inhibition	-	0.9272	92.72%
CYP1A2 inhibition	-	0.9189	91.89%
CYP2C8 inhibition	+	0.6077	60.77%
CYP inhibitory promiscuity	-	0.9374	93.74%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.5505	55.05%
Eye corrosion	-	0.9892	98.92%
Eye irritation	-	0.9071	90.71%
Skin irritation	-	0.5800	58.00%
Skin corrosion	-	0.9397	93.97%
Ames mutagenesis	-	0.5700	57.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7399	73.99%
Micronuclear	-	0.8300	83.00%
Hepatotoxicity	-	0.6375	63.75%
skin sensitisation	-	0.8829	88.29%
Respiratory toxicity	+	0.7778	77.78%
Reproductive toxicity	+	0.8667	86.67%
Mitochondrial toxicity	-	0.5125	51.25%
Nephrotoxicity	-	0.8336	83.36%
Acute Oral Toxicity (c)	I	0.7667	76.67%
Estrogen receptor binding	+	0.7963	79.63%
Androgen receptor binding	+	0.7442	74.42%
Thyroid receptor binding	-	0.5813	58.13%
Glucocorticoid receptor binding	+	0.7160	71.60%
Aromatase binding	+	0.6777	67.77%
PPAR gamma	+	0.7746	77.46%
Honey bee toxicity	-	0.5682	56.82%
Biodegradation	-	0.7000	70.00%
Crustacea aquatic toxicity	+	0.7000	70.00%
Fish aquatic toxicity	+	0.9771	97.71%

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	92.26%	91.11%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	92.04%	95.56%
CHEMBL1937	Q92769	Histone deacetylase 2	91.76%	94.75%
CHEMBL1806	P11388	DNA topoisomerase II alpha	91.68%	89.00%
CHEMBL325	Q13547	Histone deacetylase 1	90.50%	95.92%
CHEMBL1293249	Q13887	Kruppel-like factor 5	90.41%	86.33%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	89.45%	97.14%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	88.99%	96.09%
CHEMBL1994	P08235	Mineralocorticoid receptor	88.98%	100.00%
CHEMBL3714130	P46095	G-protein coupled receptor 6	88.90%	97.36%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	88.48%	94.45%
CHEMBL5608	Q16288	NT-3 growth factor receptor	87.93%	95.89%
CHEMBL241	Q14432	Phosphodiesterase 3A	87.89%	92.94%
CHEMBL253	P34972	Cannabinoid CB2 receptor	87.45%	97.25%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	86.90%	96.77%
CHEMBL2581	P07339	Cathepsin D	86.84%	98.95%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	84.47%	82.69%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	82.35%	94.00%
CHEMBL3807	P17706	T-cell protein-tyrosine phosphatase	81.18%	93.00%
CHEMBL3137262	O60341	LSD1/CoREST complex	80.99%	97.09%
CHEMBL2274	Q9H228	Sphingosine 1-phosphate receptor Edg-8	80.52%	100.00%

Plants that contains it

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

Cross-Links

• PubChem: 102052094
• NPASS: NPC277776
• LOTUS: LTS0074026
• wikiData: Q105226166