(2R,3R,4S,5S,6R)-2-[[(3R,4aS,6aS,8R,10aR,10bS)-3-[(1S)-2-hydroxy-1-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyethyl]-3,4a,7,7,10a-pentamethyl-2,5,6,6a,8,9,10,10b-octahydro-1H-benzo[f]chromen-8-yl]oxy]-6-(hydroxymethyl)oxane-3,4,5-triol

Details

• Internal ID: 4ce262e8-aad2-4cf2-9712-82fbfe5b9c3a
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Triterpenoids
• IUPAC Name: (2R,3R,4S,5S,6R)-2-[[(3R,4aS,6aS,8R,10aR,10bS)-3-[(1S)-2-hydroxy-1-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyethyl]-3,4a,7,7,10a-pentamethyl-2,5,6,6a,8,9,10,10b-octahydro-1H-benzo[f]chromen-8-yl]oxy]-6-(hydroxymethyl)oxane-3,4,5-triol
• SMILES (Canonical): CC1(C2CCC3(C(C2(CCC1OC4C(C(C(C(O4)CO)O)O)O)C)CCC(O3)(C)C(CO)OC5C(C(C(C(O5)CO)O)O)O)C)C
• SMILES (Isomeric): C[C@@]12CC[C@H](C([C@H]1CC[C@]3([C@H]2CC[C@](O3)(C)[C@H](CO)O[C@H]4[C@@H]([C@H]([C@@H]([C@H](O4)CO)O)O)O)C)(C)C)O[C@H]5[C@@H]([C@H]([C@@H]([C@H](O5)CO)O)O)O
• InChI: InChI=1S/C32H56O14/c1-29(2)17-6-10-31(4)18(30(17,3)9-8-19(29)44-27-25(40)23(38)21(36)15(12-33)42-27)7-11-32(5,46-31)20(14-35)45-28-26(41)24(39)22(37)16(13-34)43-28/h15-28,33-41H,6-14H2,1-5H3/t15-,16-,17-,18+,19-,20+,21-,22-,23+,24+,25-,26-,27+,28+,30-,31+,32-/m1/s1
• InChI Key: USMYUFNGIMZGOD-VVYIQUKOSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₃₂H₅₆O₁₄
• Molecular Weight: 664.80 g/mol
• Exact Mass: 664.36700646 g/mol
• Topological Polar Surface Area (TPSA): 228.00 Ų
• XlogP: -0.70
• Atomic LogP (AlogP): -1.47
• H-Bond Acceptor: 14
• H-Bond Donor: 9
• Rotatable Bonds: 8

Synonyms

• 1227698-64-7

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.6307	63.07%
Caco-2	-	0.8686	86.86%
Blood Brain Barrier	-	0.5750	57.50%
Human oral bioavailability	-	0.7714	77.14%
Subcellular localzation	Mitochondria	0.7531	75.31%
OATP2B1 inhibitior	-	0.8631	86.31%
OATP1B1 inhibitior	+	0.8790	87.90%
OATP1B3 inhibitior	+	0.8346	83.46%
MATE1 inhibitior	-	0.9612	96.12%
OCT2 inhibitior	-	0.5250	52.50%
BSEP inhibitior	-	0.8628	86.28%
P-glycoprotein inhibitior	+	0.6717	67.17%
P-glycoprotein substrate	-	0.8987	89.87%
CYP3A4 substrate	+	0.6957	69.57%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8278	82.78%
CYP3A4 inhibition	-	0.9654	96.54%
CYP2C9 inhibition	-	0.8873	88.73%
CYP2C19 inhibition	-	0.8785	87.85%
CYP2D6 inhibition	-	0.9633	96.33%
CYP1A2 inhibition	-	0.8933	89.33%
CYP2C8 inhibition	-	0.6664	66.64%
CYP inhibitory promiscuity	-	0.9683	96.83%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.9800	98.00%
Carcinogenicity (trinary)	Non-required	0.6893	68.93%
Eye corrosion	-	0.9898	98.98%
Eye irritation	-	0.9143	91.43%
Skin irritation	-	0.7841	78.41%
Skin corrosion	-	0.9612	96.12%
Ames mutagenesis	-	0.7370	73.70%
Human Ether-a-go-go-Related Gene inhibition	+	0.6940	69.40%
Micronuclear	-	0.9100	91.00%
Hepatotoxicity	-	0.8170	81.70%
skin sensitisation	-	0.9375	93.75%
Respiratory toxicity	-	0.5222	52.22%
Reproductive toxicity	+	0.6000	60.00%
Mitochondrial toxicity	-	0.7750	77.50%
Nephrotoxicity	-	0.5804	58.04%
Acute Oral Toxicity (c)	III	0.5036	50.36%
Estrogen receptor binding	+	0.6072	60.72%
Androgen receptor binding	+	0.6472	64.72%
Thyroid receptor binding	-	0.5609	56.09%
Glucocorticoid receptor binding	+	0.5451	54.51%
Aromatase binding	+	0.6272	62.72%
PPAR gamma	+	0.6810	68.10%
Honey bee toxicity	-	0.7100	71.00%
Biodegradation	-	0.8500	85.00%
Crustacea aquatic toxicity	-	0.7355	73.55%
Fish aquatic toxicity	+	0.8230	82.30%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL4040	P28482	MAP kinase ERK2	97.99%	83.82%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	94.49%	96.09%
CHEMBL3137262	O60341	LSD1/CoREST complex	92.53%	97.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	92.08%	91.11%
CHEMBL253	P34972	Cannabinoid CB2 receptor	88.46%	97.25%
CHEMBL237	P41145	Kappa opioid receptor	86.60%	98.10%
CHEMBL218	P21554	Cannabinoid CB1 receptor	86.15%	96.61%
CHEMBL220	P22303	Acetylcholinesterase	85.59%	94.45%
CHEMBL5608	Q16288	NT-3 growth factor receptor	84.83%	95.89%
CHEMBL2581	P07339	Cathepsin D	84.60%	98.95%
CHEMBL3880	P07900	Heat shock protein HSP 90-alpha	82.88%	96.21%
CHEMBL1994	P08235	Mineralocorticoid receptor	82.78%	100.00%
CHEMBL5255	O00206	Toll-like receptor 4	81.37%	92.50%
CHEMBL1806	P11388	DNA topoisomerase II alpha	81.20%	89.00%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	80.90%	95.89%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	80.74%	92.62%

Plants that contains it

• Achyranthes aspera
• Drimia fugax
• Garcinia kola
• Leionema bilobum
• Microtropis japonica
• Morus macroura
• Neopringlea integrifolia
• Raphanus raphanistrum
• Rhizophora mangle
• Salix alba
• Schisandra sphaerandra
• Sesbania grandiflora

Cross-Links

• PubChem: 101506967
• NPASS: NPC93284
• LOTUS: LTS0068193
• wikiData: Q105278334