(1S,4R,5R,8R,10R,13R,14R,19S,20R)-19-hydroxy-10-[(2R,3S,4S,5S)-5-hydroxy-4-[(2R,3S,4R,5R,6S)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-3-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyoxan-2-yl]oxy-4,5,9,9,13,19,20-heptamethyl-21-oxahexacyclo[18.2.2.01,18.04,17.05,14.08,13]tetracosa-15,17-dien-22-one

Details

• Internal ID: 5f1a312c-c044-4252-bd00-605ed8da40e0
• Taxonomy: Organoheterocyclic compounds > Naphthopyrans
• IUPAC Name: (1S,4R,5R,8R,10R,13R,14R,19S,20R)-19-hydroxy-10-[(2R,3S,4S,5S)-5-hydroxy-4-[(2R,3S,4R,5R,6S)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-3-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyoxan-2-yl]oxy-4,5,9,9,13,19,20-heptamethyl-21-oxahexacyclo[18.2.2.01,18.04,17.05,14.08,13]tetracosa-15,17-dien-22-one
• SMILES (Canonical): CC1C(C(C(C(O1)OC2C(C(COC2OC3CCC4(C(C3(C)C)CCC5(C4C=CC6=C7C(C8(CCC7(CCC65C)C(=O)O8)C)(C)O)C)C)O)OC9C(C(C(C(O9)CO)O)O)O)O)O)O
• SMILES (Isomeric): C[C@@H]1[C@H]([C@@H]([C@H]([C@H](O1)O[C@H]2[C@H]([C@H](CO[C@@H]2O[C@@H]3CC[C@@]4([C@H](C3(C)C)CC[C@@]5([C@@H]4C=CC6=C7[C@]([C@]8(CC[C@]7(CC[C@@]65C)C(=O)O8)C)(C)O)C)C)O)O[C@@H]9[C@H]([C@@H]([C@H]([C@@H](O9)CO)O)O)O)O)O)O
• InChI: InChI=1S/C47H72O17/c1-21-28(50)30(52)32(54)37(59-21)63-35-34(62-38-33(55)31(53)29(51)24(19-48)60-38)23(49)20-58-39(35)61-27-12-13-42(4)25(41(27,2)3)11-14-44(6)26(42)10-9-22-36-46(8,57)45(7)16-18-47(36,40(56)64-45)17-15-43(22,44)5/h9-10,21,23-35,37-39,48-55,57H,11-20H2,1-8H3/t21-,23+,24+,25+,26-,27-,28-,29+,30+,31-,32-,33+,34+,35+,37-,38-,39-,42-,43+,44-,45-,46+,47+/m1/s1
• InChI Key: ROLIIKCIEQNTMT-KRGNLLLCSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₄₇H₇₂O₁₇
• Molecular Weight: 909.10 g/mol
• Exact Mass: 908.47695082 g/mol
• Topological Polar Surface Area (TPSA): 264.00 Ų
• XlogP: 0.80
• Atomic LogP (AlogP): 0.86
• H-Bond Acceptor: 17
• H-Bond Donor: 9
• Rotatable Bonds: 7

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.7891	78.91%
Caco-2	-	0.8789	87.89%
Blood Brain Barrier	-	0.6250	62.50%
Human oral bioavailability	-	0.7571	75.71%
Subcellular localzation	Mitochondria	0.8567	85.67%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.7913	79.13%
OATP1B3 inhibitior	-	0.5700	57.00%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.6276	62.76%
BSEP inhibitior	+	0.7354	73.54%
P-glycoprotein inhibitior	+	0.7573	75.73%
P-glycoprotein substrate	+	0.5381	53.81%
CYP3A4 substrate	+	0.7442	74.42%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8686	86.86%
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	+	0.6886	68.86%
CYP inhibitory promiscuity	-	0.9668	96.68%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.9700	97.00%
Carcinogenicity (trinary)	Non-required	0.6254	62.54%
Eye corrosion	-	0.9900	99.00%
Eye irritation	-	0.9061	90.61%
Skin irritation	-	0.6103	61.03%
Skin corrosion	-	0.9480	94.80%
Ames mutagenesis	-	0.6624	66.24%
Human Ether-a-go-go-Related Gene inhibition	-	0.4303	43.03%
Micronuclear	-	0.8600	86.00%
Hepatotoxicity	-	0.6802	68.02%
skin sensitisation	-	0.8917	89.17%
Respiratory toxicity	+	0.7111	71.11%
Reproductive toxicity	+	0.9000	90.00%
Mitochondrial toxicity	-	0.7625	76.25%
Nephrotoxicity	-	0.7384	73.84%
Acute Oral Toxicity (c)	III	0.7945	79.45%
Estrogen receptor binding	+	0.7897	78.97%
Androgen receptor binding	+	0.7500	75.00%
Thyroid receptor binding	-	0.5416	54.16%
Glucocorticoid receptor binding	+	0.6913	69.13%
Aromatase binding	+	0.6464	64.64%
PPAR gamma	+	0.7717	77.17%
Honey bee toxicity	-	0.6504	65.04%
Biodegradation	-	0.7000	70.00%
Crustacea aquatic toxicity	+	0.5300	53.00%
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	99.08%	91.11%
CHEMBL2581	P07339	Cathepsin D	97.33%	98.95%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	93.91%	96.09%
CHEMBL253	P34972	Cannabinoid CB2 receptor	93.24%	97.25%
CHEMBL3137262	O60341	LSD1/CoREST complex	93.02%	97.09%
CHEMBL1293249	Q13887	Kruppel-like factor 5	92.16%	86.33%
CHEMBL1937	Q92769	Histone deacetylase 2	91.87%	94.75%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	90.95%	95.56%
CHEMBL3714130	P46095	G-protein coupled receptor 6	89.74%	97.36%
CHEMBL1806	P11388	DNA topoisomerase II alpha	89.32%	89.00%
CHEMBL1994	P08235	Mineralocorticoid receptor	87.95%	100.00%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	87.77%	94.00%
CHEMBL226	P30542	Adenosine A1 receptor	87.23%	95.93%
CHEMBL241	Q14432	Phosphodiesterase 3A	84.21%	92.94%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	82.68%	97.14%
CHEMBL1907602	P06493	Cyclin-dependent kinase 1/cyclin B1	82.35%	91.24%
CHEMBL5608	Q16288	NT-3 growth factor receptor	81.80%	95.89%
CHEMBL2274	Q9H228	Sphingosine 1-phosphate receptor Edg-8	81.51%	100.00%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	80.95%	99.23%
CHEMBL5255	O00206	Toll-like receptor 4	80.81%	92.50%
CHEMBL4208	P20618	Proteasome component C5	80.44%	90.00%

Plants that contains it

• Ilex kaushue

Cross-Links

• PubChem: 125181774
• LOTUS: LTS0225367
• wikiData: Q105242293