(2R,4aS,6aR,6aR,6bR,8aR,10S,12aR,14bS)-2,6b,9,9,12a-pentamethyl-4a-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxycarbonyl-10-[(2R,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy-2,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydro-1H-picene-6a-carboxylic acid

Details

• Internal ID: 2318e42d-e114-4537-a722-e58435e411bd
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Triterpenoids
• IUPAC Name: (2R,4aS,6aR,6aR,6bR,8aR,10S,12aR,14bS)-2,6b,9,9,12a-pentamethyl-4a-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxycarbonyl-10-[(2R,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy-2,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydro-1H-picene-6a-carboxylic acid
• SMILES (Canonical): CC1CCC2(CCC3(C(=CCC4C3(CCC5C4(CCC(C5(C)C)OC6C(C(C(C(O6)C)O)O)O)C)C)C2C1)C(=O)O)C(=O)OC7C(C(C(C(O7)CO)O)O)O
• SMILES (Isomeric): C[C@@H]1CC[C@@]2(CC[C@@]3(C(=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]([C@@H](O6)C)O)O)O)C)C)[C@@H]2C1)C(=O)O)C(=O)O[C@H]7[C@@H]([C@H]([C@@H]([C@H](O7)CO)O)O)O
• InChI: InChI=1S/C41H64O14/c1-19-9-14-40(36(51)55-34-32(48)30(46)28(44)23(18-42)53-34)15-16-41(35(49)50)21(22(40)17-19)7-8-25-38(5)12-11-26(37(3,4)24(38)10-13-39(25,41)6)54-33-31(47)29(45)27(43)20(2)52-33/h7,19-20,22-34,42-48H,8-18H2,1-6H3,(H,49,50)/t19-,20+,22+,23-,24+,25-,26+,27+,28-,29-,30+,31-,32-,33+,34+,38+,39-,40+,41-/m1/s1
• InChI Key: UMCPTEHYBYQGSW-YHZKSEHUSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₄₁H₆₄O₁₄
• Molecular Weight: 780.90 g/mol
• Exact Mass: 780.42960671 g/mol
• Topological Polar Surface Area (TPSA): 233.00 Ų
• XlogP: 2.70
• Atomic LogP (AlogP): 2.02
• H-Bond Acceptor: 13
• H-Bond Donor: 8
• Rotatable Bonds: 6

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.7941	79.41%
Caco-2	-	0.8752	87.52%
Blood Brain Barrier	-	0.6000	60.00%
Human oral bioavailability	-	0.8000	80.00%
Subcellular localzation	Mitochondria	0.8948	89.48%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.7359	73.59%
OATP1B3 inhibitior	-	0.5056	50.56%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	+	0.6474	64.74%
BSEP inhibitior	+	0.7100	71.00%
P-glycoprotein inhibitior	+	0.7414	74.14%
P-glycoprotein substrate	-	0.6809	68.09%
CYP3A4 substrate	+	0.7164	71.64%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8776	87.76%
CYP3A4 inhibition	-	0.8459	84.59%
CYP2C9 inhibition	-	0.8380	83.80%
CYP2C19 inhibition	-	0.9220	92.20%
CYP2D6 inhibition	-	0.9493	94.93%
CYP1A2 inhibition	-	0.8499	84.99%
CYP2C8 inhibition	+	0.7052	70.52%
CYP inhibitory promiscuity	-	0.9381	93.81%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9700	97.00%
Carcinogenicity (trinary)	Non-required	0.6298	62.98%
Eye corrosion	-	0.9898	98.98%
Eye irritation	-	0.9136	91.36%
Skin irritation	-	0.5723	57.23%
Skin corrosion	-	0.9450	94.50%
Ames mutagenesis	-	0.7470	74.70%
Human Ether-a-go-go-Related Gene inhibition	-	0.4074	40.74%
Micronuclear	-	0.7700	77.00%
Hepatotoxicity	-	0.8281	82.81%
skin sensitisation	-	0.9064	90.64%
Respiratory toxicity	+	0.5333	53.33%
Reproductive toxicity	+	0.8889	88.89%
Mitochondrial toxicity	-	0.6125	61.25%
Nephrotoxicity	-	0.8463	84.63%
Acute Oral Toxicity (c)	III	0.7628	76.28%
Estrogen receptor binding	+	0.7428	74.28%
Androgen receptor binding	+	0.7276	72.76%
Thyroid receptor binding	-	0.6009	60.09%
Glucocorticoid receptor binding	+	0.6450	64.50%
Aromatase binding	+	0.6243	62.43%
PPAR gamma	+	0.7169	71.69%
Honey bee toxicity	-	0.7281	72.81%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	-	0.6055	60.55%
Fish aquatic toxicity	+	0.9778	97.78%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	97.55%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	97.26%	91.11%
CHEMBL3137262	O60341	LSD1/CoREST complex	95.91%	97.09%
CHEMBL3714130	P46095	G-protein coupled receptor 6	95.23%	97.36%
CHEMBL1293249	Q13887	Kruppel-like factor 5	93.15%	86.33%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	89.62%	95.56%
CHEMBL221	P23219	Cyclooxygenase-1	85.89%	90.17%
CHEMBL2581	P07339	Cathepsin D	84.24%	98.95%
CHEMBL1806	P11388	DNA topoisomerase II alpha	84.24%	89.00%
CHEMBL5255	O00206	Toll-like receptor 4	83.90%	92.50%
CHEMBL3807	P17706	T-cell protein-tyrosine phosphatase	83.87%	93.00%
CHEMBL1994	P08235	Mineralocorticoid receptor	81.63%	100.00%
CHEMBL5028	O14672	ADAM10	81.49%	97.50%
CHEMBL3060	Q9Y345	Glycine transporter 2	81.44%	99.17%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	81.42%	95.89%

Plants that contains it

• Isertia pittieri

Cross-Links

• PubChem: 163025939
• LOTUS: LTS0213055
• wikiData: Q105275486