[(3R,4R,4aR,5R,6aR,6aS,6bR,8aR,10S,12aR,14bS)-10-[(2S,3R,4S,5S)-3-[(2S,3R,4S,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyoxan-2-yl]oxy-4-hydroxy-5-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]oxy-5-hydroxy-4a-(hydroxymethyl)-2,2,6a,6b,9,9,12a-heptamethyl-4-[(Z)-2-methylbut-2-enoyl]oxy-1,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydropicen-3-yl] (Z)-2-methylbut-2-enoate

Details

• Internal ID: 93a4c0e8-8580-458c-a3f6-cd09a959b33b
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Triterpenoids
• IUPAC Name: [(3R,4R,4aR,5R,6aR,6aS,6bR,8aR,10S,12aR,14bS)-10-[(2S,3R,4S,5S)-3-[(2S,3R,4S,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyoxan-2-yl]oxy-4-hydroxy-5-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]oxy-5-hydroxy-4a-(hydroxymethyl)-2,2,6a,6b,9,9,12a-heptamethyl-4-[(Z)-2-methylbut-2-enoyl]oxy-1,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydropicen-3-yl] (Z)-2-methylbut-2-enoate
• SMILES (Canonical): CC=C(C)C(=O)OC1C(C2(C(CC1(C)C)C3=CCC4C5(CCC(C(C5CCC4(C3(CC2O)C)C)(C)C)OC6C(C(C(CO6)OC7C(C(C(C(O7)CO)O)O)O)O)OC8C(C(C(C(O8)CO)O)O)OC9C(C(C(C(O9)C)O)O)O)C)CO)OC(=O)C(=CC)C
• SMILES (Isomeric): C/C=C(/C)\C(=O)O[C@H]1[C@@H](C(C[C@@H]2[C@]1([C@@H](C[C@@]3(C2=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)O[C@H]6[C@@H]([C@H]([C@H](CO6)O[C@H]7[C@@H]([C@H]([C@@H]([C@H](O7)CO)O)O)O)O)O[C@H]8[C@@H]([C@H]([C@@H]([C@H](O8)CO)O)O)O[C@H]9[C@@H]([C@@H]([C@H]([C@@H](O9)C)O)O)O)C)C)C)O)CO)(C)C)OC(=O)/C(=C\C)/C
• InChI: InChI=1S/C63H100O25/c1-13-27(3)52(77)87-50-51(88-53(78)28(4)14-2)63(26-66)31(21-58(50,6)7)30-15-16-36-60(10)19-18-38(59(8,9)35(60)17-20-61(36,11)62(30,12)22-37(63)67)84-56-48(42(71)34(25-79-56)83-55-47(76)44(73)40(69)32(23-64)81-55)86-57-49(45(74)41(70)33(24-65)82-57)85-54-46(75)43(72)39(68)29(5)80-54/h13-15,29,31-51,54-57,64-76H,16-26H2,1-12H3/b27-13-,28-14-/t29-,31-,32+,33+,34-,35-,36+,37+,38-,39-,40+,41+,42-,43+,44-,45-,46+,47+,48+,49+,50-,51-,54-,55-,56-,57-,60-,61+,62+,63-/m0/s1
• InChI Key: LWJWZZNVHWGNTD-SYISEXSTSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₆₃H₁₀₀O₂₅
• Molecular Weight: 1257.50 g/mol
• Exact Mass: 1256.65536867 g/mol
• Topological Polar Surface Area (TPSA): 389.00 Ų
• XlogP: 2.40
• Atomic LogP (AlogP): 0.05
• H-Bond Acceptor: 25
• H-Bond Donor: 13
• Rotatable Bonds: 15

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.7601	76.01%
Caco-2	-	0.8646	86.46%
Blood Brain Barrier	-	0.5250	52.50%
Human oral bioavailability	-	0.8286	82.86%
Subcellular localzation	Mitochondria	0.8703	87.03%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.7414	74.14%
OATP1B3 inhibitior	-	0.4610	46.10%
MATE1 inhibitior	-	0.9212	92.12%
OCT2 inhibitior	-	0.5026	50.26%
BSEP inhibitior	+	0.9755	97.55%
P-glycoprotein inhibitior	+	0.7450	74.50%
P-glycoprotein substrate	+	0.5513	55.13%
CYP3A4 substrate	+	0.7487	74.87%
CYP2C9 substrate	-	0.8033	80.33%
CYP2D6 substrate	-	0.8830	88.30%
CYP3A4 inhibition	-	0.8310	83.10%
CYP2C9 inhibition	-	0.8704	87.04%
CYP2C19 inhibition	-	0.9216	92.16%
CYP2D6 inhibition	-	0.9491	94.91%
CYP1A2 inhibition	-	0.9009	90.09%
CYP2C8 inhibition	+	0.7678	76.78%
CYP inhibitory promiscuity	-	0.9733	97.33%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9700	97.00%
Carcinogenicity (trinary)	Non-required	0.6024	60.24%
Eye corrosion	-	0.9896	98.96%
Eye irritation	-	0.8975	89.75%
Skin irritation	-	0.5876	58.76%
Skin corrosion	-	0.9441	94.41%
Ames mutagenesis	-	0.6778	67.78%
Human Ether-a-go-go-Related Gene inhibition	+	0.7831	78.31%
Micronuclear	-	0.7800	78.00%
Hepatotoxicity	-	0.8625	86.25%
skin sensitisation	-	0.9013	90.13%
Respiratory toxicity	-	0.5667	56.67%
Reproductive toxicity	+	0.9111	91.11%
Mitochondrial toxicity	-	0.6250	62.50%
Nephrotoxicity	-	0.7474	74.74%
Acute Oral Toxicity (c)	III	0.8023	80.23%
Estrogen receptor binding	+	0.7159	71.59%
Androgen receptor binding	+	0.7539	75.39%
Thyroid receptor binding	+	0.6503	65.03%
Glucocorticoid receptor binding	+	0.7920	79.20%
Aromatase binding	+	0.6801	68.01%
PPAR gamma	+	0.8050	80.50%
Honey bee toxicity	-	0.5952	59.52%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	-	0.5100	51.00%
Fish aquatic toxicity	+	0.9585	95.85%

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	99.28%	91.11%
CHEMBL221	P23219	Cyclooxygenase-1	97.67%	90.17%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	92.86%	96.09%
CHEMBL3714130	P46095	G-protein coupled receptor 6	92.74%	97.36%
CHEMBL1907602	P06493	Cyclin-dependent kinase 1/cyclin B1	89.81%	91.24%
CHEMBL1937	Q92769	Histone deacetylase 2	89.73%	94.75%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	89.30%	94.45%
CHEMBL2581	P07339	Cathepsin D	89.12%	98.95%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	88.95%	91.07%
CHEMBL3060	Q9Y345	Glycine transporter 2	88.40%	99.17%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	87.19%	95.56%
CHEMBL1293249	Q13887	Kruppel-like factor 5	87.06%	86.33%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	86.68%	94.33%
CHEMBL5608	Q16288	NT-3 growth factor receptor	86.57%	95.89%
CHEMBL2563	Q9UQL6	Histone deacetylase 5	86.37%	89.67%
CHEMBL3880	P07900	Heat shock protein HSP 90-alpha	86.16%	96.21%
CHEMBL1806	P11388	DNA topoisomerase II alpha	85.98%	89.00%
CHEMBL1994	P08235	Mineralocorticoid receptor	85.51%	100.00%
CHEMBL4187	Q99250	Sodium channel protein type II alpha subunit	84.94%	95.50%
CHEMBL2782	P35610	Acyl coenzyme A:cholesterol acyltransferase 1	84.75%	91.65%
CHEMBL3137262	O60341	LSD1/CoREST complex	83.10%	97.09%
CHEMBL5028	O14672	ADAM10	81.89%	97.50%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	80.52%	94.00%

Plants that contains it

• Lysimachia foenum-graecum

Cross-Links

• PubChem: 162946061
• LOTUS: LTS0149980
• wikiData: Q105158351