(5alpha,8alpha,9S,10beta,13E)-6alpha-[(4-O-beta-D-Glucopyranosyl-alpha-L-rhamnopyranosyl)oxy]cleroda-3,13-diene-15-ol

Details

• Internal ID: 331a55b8-6231-446b-862d-722d1fe19027
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene glycosides > Diterpene glycosides
• IUPAC Name: (2S,3R,4S,5S,6R)-2-[(2S,3R,4S,5R,6R)-6-[[(1S,3R,4S,4aR,8aR)-4-[(E)-5-hydroxy-3-methylpent-3-enyl]-3,4,8,8a-tetramethyl-1,2,3,4a,5,6-hexahydronaphthalen-1-yl]oxy]-4,5-dihydroxy-2-methyloxan-3-yl]oxy-6-(hydroxymethyl)oxane-3,4,5-triol
• SMILES (Canonical): CC1CC(C2(C(C1(C)CCC(=CCO)C)CCC=C2C)C)OC3C(C(C(C(O3)C)OC4C(C(C(C(O4)CO)O)O)O)O)O
• SMILES (Isomeric): C[C@@H]1C[C@@H]([C@@]2([C@@H]([C@@]1(C)CC/C(=C/CO)/C)CCC=C2C)C)O[C@H]3[C@@H]([C@@H]([C@H]([C@@H](O3)C)O[C@H]4[C@@H]([C@H]([C@@H]([C@H](O4)CO)O)O)O)O)O
• InChI: InChI=1S/C32H54O11/c1-16(11-13-33)10-12-31(5)18(3)14-22(32(6)17(2)8-7-9-21(31)32)42-29-27(39)25(37)28(19(4)40-29)43-30-26(38)24(36)23(35)20(15-34)41-30/h8,11,18-30,33-39H,7,9-10,12-15H2,1-6H3/b16-11+/t18-,19+,20-,21-,22+,23-,24+,25+,26-,27-,28+,29+,30+,31+,32+/m1/s1
• InChI Key: BGZWGOQCGUPNJK-FULVCJEYSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₃₂H₅₄O₁₁
• Molecular Weight: 614.80 g/mol
• Exact Mass: 614.36661253 g/mol
• Topological Polar Surface Area (TPSA): 179.00 Ų
• XlogP: 2.00
• Atomic LogP (AlogP): 1.15
• H-Bond Acceptor: 11
• H-Bond Donor: 7
• Rotatable Bonds: 9

Synonyms

• (5alpha,8alpha,9S,10beta,13E)-6alpha-[(4-O-beta-D-Glucopyranosyl-alpha-L-rhamnopyranosyl)oxy]cleroda-3,13-diene-15-ol

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.5000	50.00%
Caco-2	-	0.8695	86.95%
Blood Brain Barrier	-	0.6500	65.00%
Human oral bioavailability	-	0.7571	75.71%
Subcellular localzation	Mitochondria	0.7446	74.46%
OATP2B1 inhibitior	-	0.8620	86.20%
OATP1B1 inhibitior	+	0.8583	85.83%
OATP1B3 inhibitior	-	0.2364	23.64%
MATE1 inhibitior	-	0.9612	96.12%
OCT2 inhibitior	-	0.5750	57.50%
BSEP inhibitior	-	0.6234	62.34%
P-glycoprotein inhibitior	+	0.6277	62.77%
P-glycoprotein substrate	-	0.5980	59.80%
CYP3A4 substrate	+	0.6811	68.11%
CYP2C9 substrate	-	0.8025	80.25%
CYP2D6 substrate	-	0.8264	82.64%
CYP3A4 inhibition	-	0.9621	96.21%
CYP2C9 inhibition	-	0.9167	91.67%
CYP2C19 inhibition	-	0.8896	88.96%
CYP2D6 inhibition	-	0.9491	94.91%
CYP1A2 inhibition	-	0.8671	86.71%
CYP2C8 inhibition	+	0.5835	58.35%
CYP inhibitory promiscuity	-	0.9308	93.08%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.6680	66.80%
Eye corrosion	-	0.9903	99.03%
Eye irritation	-	0.9384	93.84%
Skin irritation	-	0.6555	65.55%
Skin corrosion	-	0.9564	95.64%
Ames mutagenesis	-	0.7070	70.70%
Human Ether-a-go-go-Related Gene inhibition	+	0.7982	79.82%
Micronuclear	-	0.9000	90.00%
Hepatotoxicity	-	0.7216	72.16%
skin sensitisation	-	0.9176	91.76%
Respiratory toxicity	-	0.5889	58.89%
Reproductive toxicity	+	0.8111	81.11%
Mitochondrial toxicity	-	0.7125	71.25%
Nephrotoxicity	-	0.7320	73.20%
Acute Oral Toxicity (c)	III	0.5149	51.49%
Estrogen receptor binding	+	0.6993	69.93%
Androgen receptor binding	+	0.6315	63.15%
Thyroid receptor binding	-	0.5545	55.45%
Glucocorticoid receptor binding	+	0.5885	58.85%
Aromatase binding	+	0.6992	69.92%
PPAR gamma	+	0.6068	60.68%
Honey bee toxicity	-	0.7044	70.44%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	+	0.5100	51.00%
Fish aquatic toxicity	+	0.9152	91.52%

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	98.80%	91.11%
CHEMBL3137262	O60341	LSD1/CoREST complex	93.29%	97.09%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	92.53%	96.09%
CHEMBL1293249	Q13887	Kruppel-like factor 5	90.67%	86.33%
CHEMBL1806	P11388	DNA topoisomerase II alpha	88.95%	89.00%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	85.93%	96.00%
CHEMBL3401	O75469	Pregnane X receptor	85.77%	94.73%
CHEMBL1994	P08235	Mineralocorticoid receptor	85.66%	100.00%
CHEMBL253	P34972	Cannabinoid CB2 receptor	85.24%	97.25%
CHEMBL3060	Q9Y345	Glycine transporter 2	85.04%	99.17%
CHEMBL241	Q14432	Phosphodiesterase 3A	84.15%	92.94%
CHEMBL4187	Q99250	Sodium channel protein type II alpha subunit	83.72%	95.50%
CHEMBL2581	P07339	Cathepsin D	83.62%	98.95%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	82.48%	95.89%
CHEMBL3476	O15111	Inhibitor of nuclear factor kappa B kinase alpha subunit	81.47%	95.83%
CHEMBL5608	Q16288	NT-3 growth factor receptor	81.28%	95.89%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	80.86%	95.56%

Plants that contains it

• Asparagus officinalis
• Astragalus dissectus
• Dicranopteris linearis
• Ocotea minarum

Cross-Links

• PubChem: 16109823
• NPASS: NPC64348
• LOTUS: LTS0059199
• wikiData: Q104935829