[(2R,3S,5S)-2,3,4,5-tetrahydroxy-6-[[(2S,3S,5S)-2,3,4-trihydroxy-6-(hydroxymethyl)-5-[(3S,4S,5S,6R)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyoxan-2-yl]oxymethyl]oxan-2-yl] (4R,5R,6aS,6bR,10S,12aR,14bR)-5-hydroxy-2,2,6a,6b,9,9,12a-heptamethyl-10-[(3S,4R,5R)-3,4,5-trihydroxyoxan-2-yl]oxy-3,4,4a,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydro-1H-picene-4-carboxylate

Details

• Internal ID: b6aa7565-da4e-4a4a-91fe-b17545b40c40
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Triterpenoids
• IUPAC Name: [(2R,3S,5S)-2,3,4,5-tetrahydroxy-6-[[(2S,3S,5S)-2,3,4-trihydroxy-6-(hydroxymethyl)-5-[(3S,4S,5S,6R)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyoxan-2-yl]oxymethyl]oxan-2-yl] (4R,5R,6aS,6bR,10S,12aR,14bR)-5-hydroxy-2,2,6a,6b,9,9,12a-heptamethyl-10-[(3S,4R,5R)-3,4,5-trihydroxyoxan-2-yl]oxy-3,4,4a,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydro-1H-picene-4-carboxylate
• SMILES (Canonical): CC1C(C(C(C(O1)OC2C(OC(C(C2O)O)(O)OCC3C(C(C(C(O3)(O)OC(=O)C4CC(CC5C4C(CC6(C5=CCC7C6(CCC8C7(CCC(C8(C)C)OC9C(C(C(CO9)O)O)O)C)C)C)O)(C)C)O)O)O)CO)O)O)O
• SMILES (Isomeric): C[C@@H]1[C@H]([C@@H]([C@@H](C(O1)O[C@@H]2C(O[C@@]([C@H](C2O)O)(O)OCC3[C@H](C([C@@H]([C@](O3)(O)OC(=O)[C@@H]4CC(C[C@@H]5C4[C@@H](C[C@@]6(C5=CCC7[C@]6(CCC8[C@@]7(CC[C@@H](C8(C)C)OC9[C@H]([C@@H]([C@@H](CO9)O)O)O)C)C)C)O)(C)C)O)O)O)CO)O)O)O
• InChI: InChI=1S/C53H86O24/c1-21-33(57)36(60)39(63)46(72-21)74-41-27(18-54)75-52(68,43(66)40(41)64)71-20-28-35(59)37(61)42(65)53(69,76-28)77-44(67)23-16-47(2,3)15-22-24-9-10-30-49(6)13-12-31(73-45-38(62)34(58)26(56)19-70-45)48(4,5)29(49)11-14-50(30,7)51(24,8)17-25(55)32(22)23/h9,21-23,25-43,45-46,54-66,68-69H,10-20H2,1-8H3/t21-,22+,23-,25-,26-,27?,28?,29?,30?,31+,32?,33-,34-,35-,36+,37?,38+,39+,40?,41-,42+,43+,45?,46?,49+,50-,51-,52+,53-/m1/s1
• InChI Key: ODKMXVVNWCFHBS-HKWQSANLSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₅₃H₈₆O₂₄
• Molecular Weight: 1107.20 g/mol
• Exact Mass: 1106.55090361 g/mol
• Topological Polar Surface Area (TPSA): 394.00 Ų
• XlogP: -1.90
• Atomic LogP (AlogP): -2.90
• H-Bond Acceptor: 24
• H-Bond Donor: 15
• Rotatable Bonds: 10

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.8467	84.67%
Caco-2	-	0.8784	87.84%
Blood Brain Barrier	-	0.5750	57.50%
Human oral bioavailability	-	0.8286	82.86%
Subcellular localzation	Mitochondria	0.8556	85.56%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.7558	75.58%
OATP1B3 inhibitior	-	0.4171	41.71%
MATE1 inhibitior	-	0.9812	98.12%
OCT2 inhibitior	-	0.6526	65.26%
BSEP inhibitior	+	0.9333	93.33%
P-glycoprotein inhibitior	+	0.7448	74.48%
P-glycoprotein substrate	+	0.6213	62.13%
CYP3A4 substrate	+	0.7413	74.13%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8801	88.01%
CYP3A4 inhibition	-	0.8829	88.29%
CYP2C9 inhibition	-	0.8581	85.81%
CYP2C19 inhibition	-	0.8759	87.59%
CYP2D6 inhibition	-	0.9330	93.30%
CYP1A2 inhibition	-	0.8595	85.95%
CYP2C8 inhibition	+	0.7821	78.21%
CYP inhibitory promiscuity	-	0.9495	94.95%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9700	97.00%
Carcinogenicity (trinary)	Non-required	0.6113	61.13%
Eye corrosion	-	0.9875	98.75%
Eye irritation	-	0.9004	90.04%
Skin irritation	-	0.6571	65.71%
Skin corrosion	-	0.9409	94.09%
Ames mutagenesis	-	0.6224	62.24%
Human Ether-a-go-go-Related Gene inhibition	+	0.7670	76.70%
Micronuclear	-	0.8500	85.00%
Hepatotoxicity	-	0.7750	77.50%
skin sensitisation	-	0.8770	87.70%
Respiratory toxicity	+	0.6111	61.11%
Reproductive toxicity	+	0.9000	90.00%
Mitochondrial toxicity	-	0.7375	73.75%
Nephrotoxicity	-	0.9075	90.75%
Acute Oral Toxicity (c)	III	0.7443	74.43%
Estrogen receptor binding	+	0.8022	80.22%
Androgen receptor binding	+	0.7602	76.02%
Thyroid receptor binding	+	0.6195	61.95%
Glucocorticoid receptor binding	+	0.7785	77.85%
Aromatase binding	+	0.6653	66.53%
PPAR gamma	+	0.8294	82.94%
Honey bee toxicity	-	0.6554	65.54%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	-	0.5205	52.05%
Fish aquatic toxicity	+	0.9552	95.52%

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	98.11%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	97.89%	91.11%
CHEMBL226	P30542	Adenosine A1 receptor	96.54%	95.93%
CHEMBL253	P34972	Cannabinoid CB2 receptor	91.81%	97.25%
CHEMBL3714130	P46095	G-protein coupled receptor 6	91.77%	97.36%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	91.68%	96.77%
CHEMBL3137262	O60341	LSD1/CoREST complex	91.12%	97.09%
CHEMBL218	P21554	Cannabinoid CB1 receptor	90.80%	96.61%
CHEMBL1994	P08235	Mineralocorticoid receptor	90.46%	100.00%
CHEMBL3880	P07900	Heat shock protein HSP 90-alpha	90.42%	96.21%
CHEMBL2581	P07339	Cathepsin D	90.05%	98.95%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	89.85%	94.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	88.40%	86.33%
CHEMBL335	P18031	Protein-tyrosine phosphatase 1B	86.85%	95.17%
CHEMBL5028	O14672	ADAM10	84.70%	97.50%
CHEMBL221	P23219	Cyclooxygenase-1	83.71%	90.17%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	83.65%	86.92%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	82.87%	97.14%
CHEMBL1806	P11388	DNA topoisomerase II alpha	82.23%	89.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	81.01%	95.56%
CHEMBL4187	Q99250	Sodium channel protein type II alpha subunit	80.98%	95.50%
CHEMBL5255	O00206	Toll-like receptor 4	80.20%	92.50%

Plants that contains it

• Oreopanax guatemalensis

Cross-Links

• PubChem: 162827472
• LOTUS: LTS0153090
• wikiData: Q105189890