(4aS,6aR,6aR,6bR,8aR,10S,12aR,14bS)-6a-[[(1R,2S)-3-[[(4aS,6aR,6aR,6bR,8aR,10S,12aR,14bS)-4a-carboxy-10-hydroxy-2,2,6b,9,9,12a-hexamethyl-1,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydropicen-6a-yl]methoxycarbonyl]-1-(3,4-dihydroxyphenyl)-6,7-dihydroxy-1,2-dihydronaphthalene-2-carbonyl]oxymethyl]-10-hydroxy-2,2,6b,9,9,12a-hexamethyl-1,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydropicene-4a-carboxylic acid

Details

• Internal ID: 1e39899b-b2e7-4d45-b76e-859cae0b54d8
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Triterpenoids
• IUPAC Name: (4aS,6aR,6aR,6bR,8aR,10S,12aR,14bS)-6a-[[(1R,2S)-3-[[(4aS,6aR,6aR,6bR,8aR,10S,12aR,14bS)-4a-carboxy-10-hydroxy-2,2,6b,9,9,12a-hexamethyl-1,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydropicen-6a-yl]methoxycarbonyl]-1-(3,4-dihydroxyphenyl)-6,7-dihydroxy-1,2-dihydronaphthalene-2-carbonyl]oxymethyl]-10-hydroxy-2,2,6b,9,9,12a-hexamethyl-1,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydropicene-4a-carboxylic acid
• SMILES (Canonical): CC1(CCC2(CCC3(C(=CCC4C3(CCC5C4(CCC(C5(C)C)O)C)C)C2C1)COC(=O)C6C(C7=CC(=C(C=C7C=C6C(=O)OCC89CCC1(CCC(CC1C8=CCC1C9(CCC2C1(CCC(C2(C)C)O)C)C)(C)C)C(=O)O)O)O)C1=CC(=C(C=C1)O)O)C(=O)O)C
• SMILES (Isomeric): C[C@]12CC[C@@H](C([C@@H]1CC[C@@]3([C@@H]2CC=C4[C@]3(CC[C@@]5([C@H]4CC(CC5)(C)C)C(=O)O)COC(=O)[C@H]6[C@@H](C7=CC(=C(C=C7C=C6C(=O)OC[C@@]89CC[C@]1(CCC(C[C@H]1C8=CC[C@H]1[C@]9(CC[C@@H]2[C@@]1(CC[C@@H](C2(C)C)O)C)C)(C)C)C(=O)O)O)O)C1=CC(=C(C=C1)O)O)C)(C)C)O
• InChI: InChI=1S/C78H106O14/c1-67(2)27-29-75(65(87)88)31-33-77(47(49(75)39-67)14-17-57-71(9)23-21-59(83)69(5,6)55(71)19-25-73(57,77)11)41-91-63(85)46-35-44-37-53(81)54(82)38-45(44)61(43-13-16-51(79)52(80)36-43)62(46)64(86)92-42-78-34-32-76(66(89)90)30-28-68(3,4)40-50(76)48(78)15-18-58-72(10)24-22-60(84)70(7,8)56(72)20-26-74(58,78)12/h13-16,35-38,49-50,55-62,79-84H,17-34,39-42H2,1-12H3,(H,87,88)(H,89,90)/t49-,50-,55-,56-,57+,58+,59-,60-,61+,62+,71-,72-,73+,74+,75-,76-,77-,78-/m0/s1
• InChI Key: QOVKXRBEKCDPME-KMLVZOICSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₇₈H₁₀₆O₁₄
• Molecular Weight: 1267.70 g/mol
• Exact Mass: 1266.75825805 g/mol
• Topological Polar Surface Area (TPSA): 249.00 Ų
• XlogP: 15.30
• Atomic LogP (AlogP): 15.20
• H-Bond Acceptor: 12
• H-Bond Donor: 8
• Rotatable Bonds: 9

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9871	98.71%
Caco-2	-	0.8553	85.53%
Blood Brain Barrier	+	0.5250	52.50%
Human oral bioavailability	-	0.7000	70.00%
Subcellular localzation	Mitochondria	0.9286	92.86%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8235	82.35%
OATP1B3 inhibitior	+	0.8066	80.66%
MATE1 inhibitior	-	0.8000	80.00%
OCT2 inhibitior	-	0.8026	80.26%
BSEP inhibitior	+	0.9862	98.62%
P-glycoprotein inhibitior	+	0.7470	74.70%
P-glycoprotein substrate	+	0.5698	56.98%
CYP3A4 substrate	+	0.7308	73.08%
CYP2C9 substrate	-	0.8004	80.04%
CYP2D6 substrate	-	0.8730	87.30%
CYP3A4 inhibition	-	0.7921	79.21%
CYP2C9 inhibition	-	0.7161	71.61%
CYP2C19 inhibition	-	0.7210	72.10%
CYP2D6 inhibition	-	0.9152	91.52%
CYP1A2 inhibition	-	0.5772	57.72%
CYP2C8 inhibition	+	0.8147	81.47%
CYP inhibitory promiscuity	-	0.8832	88.32%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9000	90.00%
Carcinogenicity (trinary)	Non-required	0.6601	66.01%
Eye corrosion	-	0.9925	99.25%
Eye irritation	-	0.8978	89.78%
Skin irritation	-	0.7346	73.46%
Skin corrosion	-	0.9573	95.73%
Ames mutagenesis	-	0.7400	74.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.6639	66.39%
Micronuclear	-	0.7100	71.00%
Hepatotoxicity	-	0.6875	68.75%
skin sensitisation	-	0.8581	85.81%
Respiratory toxicity	+	0.7333	73.33%
Reproductive toxicity	+	0.9444	94.44%
Mitochondrial toxicity	+	0.7000	70.00%
Nephrotoxicity	-	0.8854	88.54%
Acute Oral Toxicity (c)	III	0.5491	54.91%
Estrogen receptor binding	+	0.6437	64.37%
Androgen receptor binding	+	0.7784	77.84%
Thyroid receptor binding	+	0.6822	68.22%
Glucocorticoid receptor binding	+	0.7828	78.28%
Aromatase binding	+	0.6777	67.77%
PPAR gamma	+	0.8127	81.27%
Honey bee toxicity	-	0.6963	69.63%
Biodegradation	-	0.8750	87.50%
Crustacea aquatic toxicity	-	0.5605	56.05%
Fish aquatic toxicity	+	1.0000	100.00%

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	99.17%	91.11%
CHEMBL335	P18031	Protein-tyrosine phosphatase 1B	98.82%	95.17%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	97.95%	96.09%
CHEMBL3137262	O60341	LSD1/CoREST complex	97.63%	97.09%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	96.89%	94.45%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	92.58%	99.15%
CHEMBL2581	P07339	Cathepsin D	91.40%	98.95%
CHEMBL226	P30542	Adenosine A1 receptor	91.33%	95.93%
CHEMBL221	P23219	Cyclooxygenase-1	90.30%	90.17%
CHEMBL5608	Q16288	NT-3 growth factor receptor	89.04%	95.89%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	86.79%	95.56%
CHEMBL5028	O14672	ADAM10	84.79%	97.50%
CHEMBL1994	P08235	Mineralocorticoid receptor	83.72%	100.00%
CHEMBL5255	O00206	Toll-like receptor 4	83.15%	92.50%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	82.19%	82.69%
CHEMBL1293249	Q13887	Kruppel-like factor 5	81.65%	86.33%
CHEMBL340	P08684	Cytochrome P450 3A4	81.12%	91.19%
CHEMBL4685	P14902	Indoleamine 2,3-dioxygenase	80.74%	96.38%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	80.36%	90.71%

Plants that contains it

• Rhoiptelea chiliantha

Cross-Links

• PubChem: 15275972
• LOTUS: LTS0103047
• wikiData: Q105225146