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

Details

• Internal ID: 96cf9724-9c1c-4480-87fb-7d2761aafe4e
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Triterpenoids
• IUPAC Name: (3S,4aR,6aR,6aS,6bR,8aS,9R,10S,12aS)-10-[(2R,3R,4S,5S,6R)-3-[(2S,3S,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]oxy-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-3-hydroxy-2,2,6a,6b,9,12a-hexamethyl-3,4,5,6,6a,7,8,8a,9,10,11,12,13,14b-tetradecahydro-1H-picene-4a-carboxylic acid
• SMILES (Canonical): CC1C2CCC3(C(C2(CCC1OC4C(C(C(C(O4)CO)O)O)OC5C(C(C(O5)CO)O)O)C)CC=C6C3(CCC7(C6CC(C(C7)O)(C)C)C(=O)O)C)C
• SMILES (Isomeric): C[C@@H]1[C@@H]2CC[C@@]3([C@@H]([C@]2(CC[C@@H]1O[C@H]4[C@@H]([C@H]([C@@H]([C@H](O4)CO)O)O)O[C@H]5[C@H]([C@@H]([C@H](O5)CO)O)O)C)CC=C6[C@]3(CC[C@@]7(C6CC([C@H](C7)O)(C)C)C(=O)O)C)C
• InChI: InChI=1S/C40H64O13/c1-19-20-9-12-39(6)26(8-7-21-22-15-36(2,3)27(43)16-40(22,35(48)49)14-13-38(21,39)5)37(20,4)11-10-23(19)50-34-32(30(46)28(44)24(17-41)52-34)53-33-31(47)29(45)25(18-42)51-33/h7,19-20,22-34,41-47H,8-18H2,1-6H3,(H,48,49)/t19-,20+,22?,23+,24-,25-,26-,27+,28-,29-,30+,31+,32-,33+,34-,37+,38-,39-,40-/m1/s1
• InChI Key: VWJSUVPGLVPZFO-YEOBLEOFSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₄₀H₆₄O₁₃
• Molecular Weight: 752.90 g/mol
• Exact Mass: 752.43469209 g/mol
• Topological Polar Surface Area (TPSA): 216.00 Ų
• XlogP: 3.20
• Atomic LogP (AlogP): 2.10
• H-Bond Acceptor: 12
• H-Bond Donor: 8
• Rotatable Bonds: 7

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.8593	85.93%
Caco-2	-	0.8845	88.45%
Blood Brain Barrier	-	0.6500	65.00%
Human oral bioavailability	-	0.8286	82.86%
Subcellular localzation	Mitochondria	0.8538	85.38%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8080	80.80%
OATP1B3 inhibitior	-	0.2138	21.38%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.6250	62.50%
BSEP inhibitior	-	0.7769	77.69%
P-glycoprotein inhibitior	+	0.7366	73.66%
P-glycoprotein substrate	-	0.7182	71.82%
CYP3A4 substrate	+	0.7235	72.35%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8798	87.98%
CYP3A4 inhibition	-	0.9081	90.81%
CYP2C9 inhibition	-	0.8652	86.52%
CYP2C19 inhibition	-	0.9198	91.98%
CYP2D6 inhibition	-	0.9299	92.99%
CYP1A2 inhibition	-	0.9086	90.86%
CYP2C8 inhibition	+	0.6488	64.88%
CYP inhibitory promiscuity	-	0.9357	93.57%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.9700	97.00%
Carcinogenicity (trinary)	Non-required	0.5124	51.24%
Eye corrosion	-	0.9896	98.96%
Eye irritation	-	0.9181	91.81%
Skin irritation	-	0.5174	51.74%
Skin corrosion	-	0.9392	93.92%
Ames mutagenesis	-	0.8228	82.28%
Human Ether-a-go-go-Related Gene inhibition	-	0.4189	41.89%
Micronuclear	-	0.8700	87.00%
Hepatotoxicity	-	0.7342	73.42%
skin sensitisation	-	0.9021	90.21%
Respiratory toxicity	+	0.6333	63.33%
Reproductive toxicity	+	0.9444	94.44%
Mitochondrial toxicity	-	0.5750	57.50%
Nephrotoxicity	-	0.7393	73.93%
Acute Oral Toxicity (c)	III	0.6216	62.16%
Estrogen receptor binding	+	0.7427	74.27%
Androgen receptor binding	+	0.7424	74.24%
Thyroid receptor binding	-	0.6222	62.22%
Glucocorticoid receptor binding	+	0.5837	58.37%
Aromatase binding	+	0.6431	64.31%
PPAR gamma	+	0.6818	68.18%
Honey bee toxicity	-	0.7342	73.42%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	-	0.6105	61.05%
Fish aquatic toxicity	+	0.9565	95.65%

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	97.40%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	96.63%	96.09%
CHEMBL221	P23219	Cyclooxygenase-1	91.09%	90.17%
CHEMBL3137262	O60341	LSD1/CoREST complex	90.89%	97.09%
CHEMBL5255	O00206	Toll-like receptor 4	88.30%	92.50%
CHEMBL2581	P07339	Cathepsin D	87.49%	98.95%
CHEMBL1994	P08235	Mineralocorticoid receptor	87.20%	100.00%
CHEMBL3060	Q9Y345	Glycine transporter 2	86.62%	99.17%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	86.14%	94.45%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	85.36%	95.56%
CHEMBL5608	Q16288	NT-3 growth factor receptor	84.78%	95.89%
CHEMBL1293249	Q13887	Kruppel-like factor 5	84.44%	86.33%
CHEMBL4187	Q99250	Sodium channel protein type II alpha subunit	83.03%	95.50%
CHEMBL3880	P07900	Heat shock protein HSP 90-alpha	82.77%	96.21%
CHEMBL3714130	P46095	G-protein coupled receptor 6	82.13%	97.36%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	81.02%	94.33%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	80.75%	96.77%

Plants that contains it

• Cynara cardunculus

Cross-Links

• PubChem: 162857654
• LOTUS: LTS0082143
• wikiData: Q105298117