[(3R,4R,5R,6S)-6-[[(3S,5R,8S,10S,13R,14S,17S)-17-acetyl-4,4,10,13,14-pentamethyl-2,3,5,6,7,8,12,15,16,17-decahydro-1H-cyclopenta[a]phenanthren-3-yl]oxy]-5-[(2S,3R,4S,5S,6R)-5-[(2S,3R,4S,5R,6R)-4-[(2S,3R,4S,5R,6R)-3,5-dihydroxy-4-methoxy-6-(sulfooxymethyl)oxan-2-yl]oxy-3,5-dihydroxy-6-(sulfooxymethyl)oxan-2-yl]oxy-4-hydroxy-6-methyl-3-[(2S,3R,4S,5R)-3,4,5-trihydroxyoxan-2-yl]oxyoxan-2-yl]oxy-4-hydroxyoxan-3-yl] hydrogen sulfate

Details

• Internal ID: b9b26c0d-7a86-48ae-a834-7cada597c161
• Taxonomy: Organic oxygen compounds > Organooxygen compounds > Carbohydrates and carbohydrate conjugates > Oligosaccharides > Oligosaccharide sulfates
• IUPAC Name: [(3R,4R,5R,6S)-6-[[(3S,5R,8S,10S,13R,14S,17S)-17-acetyl-4,4,10,13,14-pentamethyl-2,3,5,6,7,8,12,15,16,17-decahydro-1H-cyclopenta[a]phenanthren-3-yl]oxy]-5-[(2S,3R,4S,5S,6R)-5-[(2S,3R,4S,5R,6R)-4-[(2S,3R,4S,5R,6R)-3,5-dihydroxy-4-methoxy-6-(sulfooxymethyl)oxan-2-yl]oxy-3,5-dihydroxy-6-(sulfooxymethyl)oxan-2-yl]oxy-4-hydroxy-6-methyl-3-[(2S,3R,4S,5R)-3,4,5-trihydroxyoxan-2-yl]oxyoxan-2-yl]oxy-4-hydroxyoxan-3-yl] hydrogen sulfate
• SMILES (Canonical): CC1C(C(C(C(O1)OC2C(C(COC2OC3CCC4(C(C3(C)C)CCC5C4=CCC6(C5(CCC6C(=O)C)C)C)C)OS(=O)(=O)O)O)OC7C(C(C(CO7)O)O)O)O)OC8C(C(C(C(O8)COS(=O)(=O)O)O)OC9C(C(C(C(O9)COS(=O)(=O)O)O)OC)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@@H]5C4=CC[C@]6([C@]5(CC[C@@H]6C(=O)C)C)C)C)OS(=O)(=O)O)O)O[C@H]7[C@@H]([C@H]([C@@H](CO7)O)O)O)O)O[C@H]8[C@@H]([C@H]([C@@H]([C@H](O8)COS(=O)(=O)O)O)O[C@H]9[C@@H]([C@H]([C@@H]([C@H](O9)COS(=O)(=O)O)O)OC)O)O
• InChI: InChI=1S/C53H86O33S3/c1-21(54)23-11-15-53(7)25-9-10-30-50(3,4)31(13-14-51(30,5)24(25)12-16-52(23,53)6)81-48-43(35(59)29(18-75-48)86-89(70,71)72)85-49-44(84-45-36(60)32(56)26(55)17-74-45)37(61)40(22(2)78-49)82-47-39(63)42(34(58)28(80-47)20-77-88(67,68)69)83-46-38(62)41(73-8)33(57)27(79-46)19-76-87(64,65)66/h12,22-23,25-49,55-63H,9-11,13-20H2,1-8H3,(H,64,65,66)(H,67,68,69)(H,70,71,72)/t22-,23-,25-,26-,27-,28-,29-,30+,31+,32+,33-,34-,35+,36-,37+,38-,39-,40-,41+,42+,43-,44-,45+,46+,47+,48+,49+,51-,52-,53+/m1/s1
• InChI Key: YOKKWAMWHXWVML-FJJOPCRESA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₅₃H₈₆O₃₃S₃
• Molecular Weight: 1347.40 g/mol
• Exact Mass: 1346.4213487 g/mol
• Topological Polar Surface Area (TPSA): 517.00 Ų
• XlogP: -3.90
• Atomic LogP (AlogP): -2.90
• H-Bond Acceptor: 30
• H-Bond Donor: 12
• Rotatable Bonds: 20

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.8666	86.66%
Caco-2	-	0.8616	86.16%
Blood Brain Barrier	+	0.6000	60.00%
Human oral bioavailability	-	0.7143	71.43%
Subcellular localzation	Mitochondria	0.5609	56.09%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8066	80.66%
OATP1B3 inhibitior	+	0.9200	92.00%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.8750	87.50%
BSEP inhibitior	+	0.9515	95.15%
P-glycoprotein inhibitior	+	0.7443	74.43%
P-glycoprotein substrate	+	0.7092	70.92%
CYP3A4 substrate	+	0.7406	74.06%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8590	85.90%
CYP3A4 inhibition	-	0.8457	84.57%
CYP2C9 inhibition	-	0.7489	74.89%
CYP2C19 inhibition	-	0.7219	72.19%
CYP2D6 inhibition	-	0.8695	86.95%
CYP1A2 inhibition	-	0.7525	75.25%
CYP2C8 inhibition	+	0.7826	78.26%
CYP inhibitory promiscuity	-	0.9074	90.74%
UGT catelyzed	+	0.9000	90.00%
Carcinogenicity (binary)	-	0.5900	59.00%
Carcinogenicity (trinary)	Non-required	0.5629	56.29%
Eye corrosion	-	0.9798	97.98%
Eye irritation	-	0.8975	89.75%
Skin irritation	-	0.7561	75.61%
Skin corrosion	-	0.9107	91.07%
Ames mutagenesis	-	0.6300	63.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.6753	67.53%
Micronuclear	+	0.5800	58.00%
Hepatotoxicity	-	0.6084	60.84%
skin sensitisation	-	0.8447	84.47%
Respiratory toxicity	-	0.5111	51.11%
Reproductive toxicity	+	0.9667	96.67%
Mitochondrial toxicity	+	0.5875	58.75%
Nephrotoxicity	-	0.9280	92.80%
Acute Oral Toxicity (c)	III	0.5750	57.50%
Estrogen receptor binding	+	0.7571	75.71%
Androgen receptor binding	+	0.7477	74.77%
Thyroid receptor binding	+	0.6335	63.35%
Glucocorticoid receptor binding	+	0.7692	76.92%
Aromatase binding	+	0.6520	65.20%
PPAR gamma	+	0.8239	82.39%
Honey bee toxicity	-	0.6323	63.23%
Biodegradation	-	0.7500	75.00%
Crustacea aquatic toxicity	+	0.5245	52.45%
Fish aquatic toxicity	+	0.9881	98.81%

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	97.93%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	97.60%	96.09%
CHEMBL241	Q14432	Phosphodiesterase 3A	95.47%	92.94%
CHEMBL2581	P07339	Cathepsin D	94.41%	98.95%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	89.85%	94.00%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	88.64%	94.33%
CHEMBL5608	Q16288	NT-3 growth factor receptor	88.25%	95.89%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	86.90%	95.89%
CHEMBL1994	P08235	Mineralocorticoid receptor	86.59%	100.00%
CHEMBL5255	O00206	Toll-like receptor 4	86.05%	92.50%
CHEMBL3714130	P46095	G-protein coupled receptor 6	85.82%	97.36%
CHEMBL340	P08684	Cytochrome P450 3A4	85.79%	91.19%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	85.71%	95.56%
CHEMBL1806	P11388	DNA topoisomerase II alpha	85.68%	89.00%
CHEMBL2179	P04062	Beta-glucocerebrosidase	84.05%	85.31%
CHEMBL5028	O14672	ADAM10	83.69%	97.50%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	83.65%	96.00%
CHEMBL3476	O15111	Inhibitor of nuclear factor kappa B kinase alpha subunit	83.63%	95.83%
CHEMBL226	P30542	Adenosine A1 receptor	82.81%	95.93%
CHEMBL3137262	O60341	LSD1/CoREST complex	82.46%	97.09%
CHEMBL2274	Q9H228	Sphingosine 1-phosphate receptor Edg-8	81.73%	100.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	81.48%	86.33%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	80.87%	86.92%

Plants that contains it

• Citrus aurantiifolia

Cross-Links

• PubChem: 10920380
• NPASS: NPC158296