(4aR,6aR,6aS,6bR,8aR,10S,12aR,14bR)-10-[(2S,3R,4S,5S)-3-[(2S,3R,4R,5S,6S)-4-[(2S,3R,4R,5R)-5-[(2R,3R,4R,5S,6R)-3,4-dihydroxy-6-(hydroxymethyl)-5-[(2S,3R,4S,5S,6S)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]oxy-3,4-dihydroxyoxan-2-yl]oxy-3,5-dihydroxy-6-methyloxan-2-yl]oxy-4,5-dihydroxyoxan-2-yl]oxy-2,2,6a,6b,9,9,12a-heptamethyl-1,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydropicene-4a-carboxylic acid

Details

• Internal ID: c2b2bdc1-b5f4-491b-b941-0c80d13f044b
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Triterpenoids
• IUPAC Name: (4aR,6aR,6aS,6bR,8aR,10S,12aR,14bR)-10-[(2S,3R,4S,5S)-3-[(2S,3R,4R,5S,6S)-4-[(2S,3R,4R,5R)-5-[(2R,3R,4R,5S,6R)-3,4-dihydroxy-6-(hydroxymethyl)-5-[(2S,3R,4S,5S,6S)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]oxy-3,4-dihydroxyoxan-2-yl]oxy-3,5-dihydroxy-6-methyloxan-2-yl]oxy-4,5-dihydroxyoxan-2-yl]oxy-2,2,6a,6b,9,9,12a-heptamethyl-1,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydropicene-4a-carboxylic acid
• SMILES (Canonical): CC1C(C(C(C(O1)OC2C(C(COC2OC3CCC4(C(C3(C)C)CCC5(C4CC=C6C5(CCC7(C6CC(CC7)(C)C)C(=O)O)C)C)C)O)O)O)OC8C(C(C(CO8)OC9C(C(C(C(O9)CO)OC1C(C(C(C(O1)CO)O)O)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](C3(C)C)CC[C@@]5([C@@H]4CC=C6[C@]5(CC[C@]7([C@@H]6CC(CC7)(C)C)C(=O)O)C)C)C)O)O)O)O[C@H]8[C@@H]([C@H]([C@@H](CO8)O[C@H]9[C@@H]([C@H]([C@@H]([C@H](O9)CO)O[C@H]1[C@@H]([C@H]([C@@H]([C@@H](O1)CO)O)O)O)O)O)O)O)O
• InChI: InChI=1S/C58H94O25/c1-24-34(62)45(82-47-40(68)37(65)30(23-75-47)79-48-42(70)39(67)44(29(21-60)78-48)81-49-41(69)38(66)36(64)28(20-59)77-49)43(71)50(76-24)83-46-35(63)27(61)22-74-51(46)80-33-12-13-55(6)31(54(33,4)5)11-14-57(8)32(55)10-9-25-26-19-53(2,3)15-17-58(26,52(72)73)18-16-56(25,57)7/h9,24,26-51,59-71H,10-23H2,1-8H3,(H,72,73)/t24-,26+,27-,28-,29+,30+,31-,32+,33-,34-,35-,36+,37-,38-,39+,40+,41+,42+,43+,44+,45+,46+,47-,48-,49-,50-,51-,55-,56+,57+,58+/m0/s1
• InChI Key: NXEDMPWHCDPWDO-GUEONUCXSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₅₈H₉₄O₂₅
• Molecular Weight: 1191.30 g/mol
• Exact Mass: 1190.60841848 g/mol
• Topological Polar Surface Area (TPSA): 393.00 Ų
• XlogP: -0.40
• Atomic LogP (AlogP): -1.34
• H-Bond Acceptor: 24
• H-Bond Donor: 14
• Rotatable Bonds: 13

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.7891	78.91%
Caco-2	-	0.8721	87.21%
Blood Brain Barrier	-	0.6250	62.50%
Human oral bioavailability	-	0.7714	77.14%
Subcellular localzation	Mitochondria	0.8567	85.67%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.6893	68.93%
OATP1B3 inhibitior	-	0.5700	57.00%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.6276	62.76%
BSEP inhibitior	+	0.9085	90.85%
P-glycoprotein inhibitior	+	0.7448	74.48%
P-glycoprotein substrate	-	0.5718	57.18%
CYP3A4 substrate	+	0.7371	73.71%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8798	87.98%
CYP3A4 inhibition	-	0.9300	93.00%
CYP2C9 inhibition	-	0.8838	88.38%
CYP2C19 inhibition	-	0.9101	91.01%
CYP2D6 inhibition	-	0.9422	94.22%
CYP1A2 inhibition	-	0.8933	89.33%
CYP2C8 inhibition	+	0.7524	75.24%
CYP inhibitory promiscuity	-	0.9668	96.68%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9700	97.00%
Carcinogenicity (trinary)	Non-required	0.6254	62.54%
Eye corrosion	-	0.9900	99.00%
Eye irritation	-	0.8995	89.95%
Skin irritation	-	0.6103	61.03%
Skin corrosion	-	0.9480	94.80%
Ames mutagenesis	-	0.7100	71.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7884	78.84%
Micronuclear	-	0.8600	86.00%
Hepatotoxicity	-	0.9625	96.25%
skin sensitisation	-	0.8917	89.17%
Respiratory toxicity	-	0.5111	51.11%
Reproductive toxicity	+	0.9000	90.00%
Mitochondrial toxicity	-	0.7625	76.25%
Nephrotoxicity	-	0.9495	94.95%
Acute Oral Toxicity (c)	III	0.7945	79.45%
Estrogen receptor binding	+	0.8004	80.04%
Androgen receptor binding	+	0.7385	73.85%
Thyroid receptor binding	+	0.6030	60.30%
Glucocorticoid receptor binding	+	0.7712	77.12%
Aromatase binding	+	0.6628	66.28%
PPAR gamma	+	0.8241	82.41%
Honey bee toxicity	-	0.6451	64.51%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	-	0.5205	52.05%
Fish aquatic toxicity	+	0.9411	94.11%

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	98.44%	91.11%
CHEMBL335	P18031	Protein-tyrosine phosphatase 1B	98.25%	95.17%
CHEMBL3714130	P46095	G-protein coupled receptor 6	94.09%	97.36%
CHEMBL221	P23219	Cyclooxygenase-1	93.07%	90.17%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	92.16%	96.09%
CHEMBL1293249	Q13887	Kruppel-like factor 5	92.06%	86.33%
CHEMBL3137262	O60341	LSD1/CoREST complex	91.66%	97.09%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	90.63%	94.45%
CHEMBL2581	P07339	Cathepsin D	89.96%	98.95%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	87.41%	96.77%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	87.17%	95.56%
CHEMBL1806	P11388	DNA topoisomerase II alpha	86.59%	89.00%
CHEMBL5028	O14672	ADAM10	83.59%	97.50%
CHEMBL5608	Q16288	NT-3 growth factor receptor	83.18%	95.89%
CHEMBL1994	P08235	Mineralocorticoid receptor	80.80%	100.00%
CHEMBL4187	Q99250	Sodium channel protein type II alpha subunit	80.70%	95.50%
CHEMBL3713062	P10646	Tissue factor pathway inhibitor	80.50%	97.33%
CHEMBL3060	Q9Y345	Glycine transporter 2	80.25%	99.17%

Plants that contains it

• Clematis chinensis

Cross-Links

• PubChem: 162919933
• LOTUS: LTS0112553
• wikiData: Q105187132