(1R,2R,5S,7R,10R,11R,14R,15S,18S,23S)-2,10,14,15,21,21-hexamethyl-7-[(1R,2S,3S)-2,3,4-trihydroxy-1-[(2S,3R,4S,5S)-3,4,5-trihydroxyoxan-2-yl]oxybutyl]-6,8-dioxahexacyclo[12.12.0.02,11.05,10.015,24.018,23]hexacos-24-ene-18-carboxylic acid

Details

• Internal ID: 29dcc17c-97e3-44dd-9afb-a75730ce046a
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Triterpenoids
• IUPAC Name: (1R,2R,5S,7R,10R,11R,14R,15S,18S,23S)-2,10,14,15,21,21-hexamethyl-7-[(1R,2S,3S)-2,3,4-trihydroxy-1-[(2S,3R,4S,5S)-3,4,5-trihydroxyoxan-2-yl]oxybutyl]-6,8-dioxahexacyclo[12.12.0.02,11.05,10.015,24.018,23]hexacos-24-ene-18-carboxylic acid
• SMILES (Canonical): CC1(CCC2(CCC3(C(=CCC4C3(CCC5C4(CCC6C5(COC(O6)C(C(C(CO)O)O)OC7C(C(C(CO7)O)O)O)C)C)C)C2C1)C)C(=O)O)C
• SMILES (Isomeric): C[C@]12CC[C@H]3[C@]([C@@H]1CC[C@@]4([C@@H]2CC=C5[C@]4(CC[C@@]6([C@H]5CC(CC6)(C)C)C(=O)O)C)C)(CO[C@H](O3)[C@@H]([C@H]([C@H](CO)O)O)O[C@H]7[C@@H]([C@H]([C@H](CO7)O)O)O)C
• InChI: InChI=1S/C40H64O12/c1-35(2)13-15-40(34(47)48)16-14-38(5)21(22(40)17-35)7-8-26-36(3)11-10-27-37(4,25(36)9-12-39(26,38)6)20-50-33(51-27)31(29(45)23(42)18-41)52-32-30(46)28(44)24(43)19-49-32/h7,22-33,41-46H,8-20H2,1-6H3,(H,47,48)/t22-,23-,24-,25+,26+,27-,28-,29-,30+,31+,32-,33+,36-,37-,38+,39+,40-/m0/s1
• InChI Key: FFYYBJYOGKIPMJ-MATOHKANSA-N
• Popularity: 2 references in papers

Physical and Chemical Properties

• Molecular Formula: C₄₀H₆₄O₁₂
• Molecular Weight: 736.90 g/mol
• Exact Mass: 736.43977747 g/mol
• Topological Polar Surface Area (TPSA): 196.00 Ų
• XlogP: 3.20
• Atomic LogP (AlogP): 3.13
• H-Bond Acceptor: 11
• H-Bond Donor: 7
• Rotatable Bonds: 7

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	-	0.8732	87.32%
Blood Brain Barrier	-	0.6250	62.50%
Human oral bioavailability	-	0.7143	71.43%
Subcellular localzation	Mitochondria	0.8567	85.67%
OATP2B1 inhibitior	-	0.8700	87.00%
OATP1B1 inhibitior	+	0.7863	78.63%
OATP1B3 inhibitior	-	0.5700	57.00%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.6276	62.76%
BSEP inhibitior	-	0.4885	48.85%
P-glycoprotein inhibitior	+	0.7534	75.34%
P-glycoprotein substrate	+	0.5540	55.40%
CYP3A4 substrate	+	0.7225	72.25%
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	+	0.6698	66.98%
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	-	0.9179	91.79%
Skin irritation	-	0.6103	61.03%
Skin corrosion	-	0.9480	94.80%
Ames mutagenesis	-	0.6600	66.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.6538	65.38%
Micronuclear	-	0.8600	86.00%
Hepatotoxicity	-	0.8518	85.18%
skin sensitisation	-	0.8917	89.17%
Respiratory toxicity	+	0.6556	65.56%
Reproductive toxicity	+	0.9000	90.00%
Mitochondrial toxicity	-	0.7625	76.25%
Nephrotoxicity	-	0.7041	70.41%
Acute Oral Toxicity (c)	III	0.7945	79.45%
Estrogen receptor binding	+	0.7099	70.99%
Androgen receptor binding	+	0.7195	71.95%
Thyroid receptor binding	-	0.6316	63.16%
Glucocorticoid receptor binding	+	0.5884	58.84%
Aromatase binding	+	0.6495	64.95%
PPAR gamma	+	0.6636	66.36%
Honey bee toxicity	-	0.7598	75.98%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	-	0.6450	64.50%
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
CHEMBL335	P18031	Protein-tyrosine phosphatase 1B	98.61%	95.17%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	98.02%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	97.41%	96.09%
CHEMBL3137262	O60341	LSD1/CoREST complex	95.96%	97.09%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	93.82%	94.45%
CHEMBL2581	P07339	Cathepsin D	93.75%	98.95%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	92.87%	96.77%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	89.49%	95.56%
CHEMBL221	P23219	Cyclooxygenase-1	85.86%	90.17%
CHEMBL5028	O14672	ADAM10	84.37%	97.50%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	82.75%	86.92%
CHEMBL1806	P11388	DNA topoisomerase II alpha	82.12%	89.00%
CHEMBL4302	P08183	P-glycoprotein 1	80.46%	92.98%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	80.21%	82.69%
CHEMBL5163	Q9NY46	Sodium channel protein type III alpha subunit	80.19%	96.90%

Plants that contains it

• Anemoclema glaucifolium

Cross-Links

• PubChem: 101927628
• LOTUS: LTS0160982
• wikiData: Q104994742