(4aS,6aR,6aS,6bR,8aS,10S,12aR,14bS)-10-[(2S,3R,4S,5R)-3-[(2S,3R,4S,5R,6R)-3,5-dihydroxy-4-[(2S,3R,4S,5S)-3,4,5-trihydroxyoxan-2-yl]oxy-6-[[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-[[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-[[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxymethyl]oxan-2-yl]oxymethyl]oxan-2-yl]oxymethyl]oxan-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: e4c7b8ee-e38f-44c3-9df2-bffe772d523b
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Triterpenoids
• IUPAC Name: (4aS,6aR,6aS,6bR,8aS,10S,12aR,14bS)-10-[(2S,3R,4S,5R)-3-[(2S,3R,4S,5R,6R)-3,5-dihydroxy-4-[(2S,3R,4S,5S)-3,4,5-trihydroxyoxan-2-yl]oxy-6-[[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-[[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-[[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxymethyl]oxan-2-yl]oxymethyl]oxan-2-yl]oxymethyl]oxan-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): CC1(CCC2(CCC3(C(=CCC4C3(CCC5C4(CCC(C5(C)C)OC6C(C(C(CO6)O)O)OC7C(C(C(C(O7)COC8C(C(C(C(O8)COC9C(C(C(C(O9)COC3C(C(C(C(O3)CO)O)O)O)O)O)O)O)O)O)O)OC3C(C(C(CO3)O)O)O)O)C)C)C2C1)C)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)C)C)(C)C)O[C@H]6[C@@H]([C@H]([C@@H](CO6)O)O)O[C@H]7[C@@H]([C@H]([C@@H]([C@H](O7)CO[C@H]8[C@@H]([C@H]([C@@H]([C@H](O8)CO[C@H]9[C@@H]([C@H]([C@@H]([C@H](O9)CO[C@H]1[C@@H]([C@H]([C@@H]([C@H](O1)CO)O)O)O)O)O)O)O)O)O)O)O[C@H]1[C@@H]([C@H]([C@H](CO1)O)O)O)O
• InChI: InChI=1S/C64H104O31/c1-59(2)14-16-64(58(82)83)17-15-62(6)25(26(64)18-59)8-9-34-61(5)12-11-35(60(3,4)33(61)10-13-63(34,62)7)93-57-51(37(69)28(67)21-85-57)95-56-49(81)50(94-55-45(77)36(68)27(66)20-84-55)41(73)32(92-56)24-88-54-48(80)44(76)40(72)31(91-54)23-87-53-47(79)43(75)39(71)30(90-53)22-86-52-46(78)42(74)38(70)29(19-65)89-52/h8,26-57,65-81H,9-24H2,1-7H3,(H,82,83)/t26-,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+,52+,53+,54+,55-,56-,57-,61-,62+,63+,64-/m0/s1
• InChI Key: BZFYSUCICLFIOI-DYACXSTCSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₆₄H₁₀₄O₃₁
• Molecular Weight: 1369.50 g/mol
• Exact Mass: 1368.6561565 g/mol
• Topological Polar Surface Area (TPSA): 492.00 Ų
• XlogP: -3.60
• Atomic LogP (AlogP): -4.54
• H-Bond Acceptor: 30
• H-Bond Donor: 18
• Rotatable Bonds: 17

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	-	0.8675	86.75%
Blood Brain Barrier	-	0.6250	62.50%
Human oral bioavailability	-	0.7429	74.29%
Subcellular localzation	Mitochondria	0.8567	85.67%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.7289	72.89%
OATP1B3 inhibitior	-	0.5700	57.00%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.6276	62.76%
BSEP inhibitior	+	0.9196	91.96%
P-glycoprotein inhibitior	+	0.7435	74.35%
P-glycoprotein substrate	-	0.6776	67.76%
CYP3A4 substrate	+	0.7304	73.04%
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	+	0.7200	72.00%
CYP inhibitory promiscuity	-	0.9668	96.68%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.9700	97.00%
Carcinogenicity (trinary)	Non-required	0.6254	62.54%
Eye corrosion	-	0.9900	99.00%
Eye irritation	-	0.8978	89.78%
Skin irritation	-	0.6103	61.03%
Skin corrosion	-	0.9480	94.80%
Ames mutagenesis	-	0.7070	70.70%
Human Ether-a-go-go-Related Gene inhibition	+	0.7741	77.41%
Micronuclear	-	0.8600	86.00%
Hepatotoxicity	-	0.9125	91.25%
skin sensitisation	-	0.8917	89.17%
Respiratory toxicity	-	0.5222	52.22%
Reproductive toxicity	+	0.9000	90.00%
Mitochondrial toxicity	-	0.7625	76.25%
Nephrotoxicity	-	0.8148	81.48%
Acute Oral Toxicity (c)	III	0.7945	79.45%
Estrogen receptor binding	+	0.7622	76.22%
Androgen receptor binding	+	0.7408	74.08%
Thyroid receptor binding	+	0.6552	65.52%
Glucocorticoid receptor binding	+	0.7626	76.26%
Aromatase binding	+	0.6602	66.02%
PPAR gamma	+	0.8102	81.02%
Honey bee toxicity	-	0.7018	70.18%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	-	0.6205	62.05%
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	97.67%	91.11%
CHEMBL335	P18031	Protein-tyrosine phosphatase 1B	96.23%	95.17%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	95.47%	96.09%
CHEMBL3137262	O60341	LSD1/CoREST complex	94.06%	97.09%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	93.30%	94.45%
CHEMBL1293249	Q13887	Kruppel-like factor 5	88.66%	86.33%
CHEMBL221	P23219	Cyclooxygenase-1	87.11%	90.17%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	86.42%	96.77%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	86.40%	95.56%
CHEMBL3714130	P46095	G-protein coupled receptor 6	86.24%	97.36%
CHEMBL5255	O00206	Toll-like receptor 4	85.92%	92.50%
CHEMBL2581	P07339	Cathepsin D	85.70%	98.95%
CHEMBL4187	Q99250	Sodium channel protein type II alpha subunit	84.21%	95.50%
CHEMBL5028	O14672	ADAM10	83.93%	97.50%
CHEMBL226	P30542	Adenosine A1 receptor	83.46%	95.93%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	81.96%	94.33%
CHEMBL5608	Q16288	NT-3 growth factor receptor	80.66%	95.89%
CHEMBL1994	P08235	Mineralocorticoid receptor	80.18%	100.00%

Plants that contains it

• Gundelia tournefortii

Cross-Links

• PubChem: 163192096
• LOTUS: LTS0117738
• wikiData: Q104950441