(4S,5R,8S,13R,16S,19R,22R)-8-[(2R,4R,5R,6R)-4-methoxy-6-methyl-5-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-[[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxymethyl]oxan-2-yl]oxyoxan-2-yl]oxy-5,19-dimethyl-15,18,20-trioxapentacyclo[14.5.1.04,13.05,10.019,22]docosa-1(21),10-dien-14-one

Details

• Internal ID: 414218cc-bd2d-4823-8512-c5d32d4110c6
• Taxonomy: Organic oxygen compounds > Organooxygen compounds > Carbohydrates and carbohydrate conjugates > Glycosyl compounds > O-glycosyl compounds
• IUPAC Name: (4S,5R,8S,13R,16S,19R,22R)-8-[(2R,4R,5R,6R)-4-methoxy-6-methyl-5-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-[[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxymethyl]oxan-2-yl]oxyoxan-2-yl]oxy-5,19-dimethyl-15,18,20-trioxapentacyclo[14.5.1.04,13.05,10.019,22]docosa-1(21),10-dien-14-one
• SMILES (Canonical): CC1C(C(CC(O1)OC2CCC3(C4CCC5=COC6(C5C(CO6)OC(=O)C4CC=C3C2)C)C)OC)OC7C(C(C(C(O7)COC8C(C(C(C(O8)CO)O)O)O)O)O)O
• SMILES (Isomeric): C[C@@H]1[C@H]([C@@H](C[C@@H](O1)O[C@H]2CC[C@@]3([C@H]4CCC5=CO[C@@]6([C@H]5[C@@H](CO6)OC(=O)[C@@H]4CC=C3C2)C)C)OC)O[C@H]7[C@@H]([C@H]([C@@H]([C@H](O7)CO[C@H]8[C@@H]([C@H]([C@@H]([C@H](O8)CO)O)O)O)O)O)O
• InChI: InChI=1S/C40H60O18/c1-17-35(58-38-34(47)32(45)30(43)26(57-38)15-50-37-33(46)31(44)29(42)24(13-41)56-37)23(49-4)12-27(53-17)54-20-9-10-39(2)19(11-20)6-7-21-22(39)8-5-18-14-51-40(3)28(18)25(16-52-40)55-36(21)48/h6,14,17,20-35,37-38,41-47H,5,7-13,15-16H2,1-4H3/t17-,20+,21-,22+,23-,24-,25-,26-,27+,28-,29-,30-,31+,32+,33-,34-,35-,37-,38+,39+,40+/m1/s1
• InChI Key: RARMLHQTRDHVBR-HDJFROFOSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₄₀H₆₀O₁₈
• Molecular Weight: 828.90 g/mol
• Exact Mass: 828.37796506 g/mol
• Topological Polar Surface Area (TPSA): 251.00 Ų
• XlogP: -1.30
• Atomic LogP (AlogP): -0.73
• H-Bond Acceptor: 18
• H-Bond Donor: 7
• Rotatable Bonds: 9

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.7890	78.90%
Caco-2	-	0.8813	88.13%
Blood Brain Barrier	-	0.7250	72.50%
Human oral bioavailability	-	0.7857	78.57%
Subcellular localzation	Mitochondria	0.8222	82.22%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8357	83.57%
OATP1B3 inhibitior	+	0.8804	88.04%
MATE1 inhibitior	-	0.9612	96.12%
OCT2 inhibitior	-	0.7250	72.50%
BSEP inhibitior	+	0.8316	83.16%
P-glycoprotein inhibitior	+	0.7311	73.11%
P-glycoprotein substrate	+	0.6996	69.96%
CYP3A4 substrate	+	0.7447	74.47%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8872	88.72%
CYP3A4 inhibition	-	0.9572	95.72%
CYP2C9 inhibition	-	0.9237	92.37%
CYP2C19 inhibition	-	0.9117	91.17%
CYP2D6 inhibition	-	0.9405	94.05%
CYP1A2 inhibition	-	0.9029	90.29%
CYP2C8 inhibition	+	0.6975	69.75%
CYP inhibitory promiscuity	-	0.9162	91.62%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.5310	53.10%
Eye corrosion	-	0.9889	98.89%
Eye irritation	-	0.9153	91.53%
Skin irritation	-	0.5709	57.09%
Skin corrosion	-	0.9418	94.18%
Ames mutagenesis	-	0.7754	77.54%
Human Ether-a-go-go-Related Gene inhibition	+	0.7693	76.93%
Micronuclear	-	0.8600	86.00%
Hepatotoxicity	-	0.7625	76.25%
skin sensitisation	-	0.9169	91.69%
Respiratory toxicity	+	0.7000	70.00%
Reproductive toxicity	+	0.9222	92.22%
Mitochondrial toxicity	+	0.5125	51.25%
Nephrotoxicity	-	0.6990	69.90%
Acute Oral Toxicity (c)	III	0.4156	41.56%
Estrogen receptor binding	+	0.8361	83.61%
Androgen receptor binding	+	0.7147	71.47%
Thyroid receptor binding	-	0.5558	55.58%
Glucocorticoid receptor binding	+	0.7088	70.88%
Aromatase binding	+	0.6457	64.57%
PPAR gamma	+	0.7689	76.89%
Honey bee toxicity	-	0.6123	61.23%
Biodegradation	-	0.7500	75.00%
Crustacea aquatic toxicity	-	0.5000	50.00%
Fish aquatic toxicity	+	0.9276	92.76%

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%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	98.26%	85.14%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	97.79%	96.09%
CHEMBL253	P34972	Cannabinoid CB2 receptor	96.44%	97.25%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	95.50%	94.45%
CHEMBL2581	P07339	Cathepsin D	93.73%	98.95%
CHEMBL1994	P08235	Mineralocorticoid receptor	93.08%	100.00%
CHEMBL3137262	O60341	LSD1/CoREST complex	92.19%	97.09%
CHEMBL1806	P11388	DNA topoisomerase II alpha	90.78%	89.00%
CHEMBL226	P30542	Adenosine A1 receptor	89.88%	95.93%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	89.04%	95.89%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	87.46%	94.00%
CHEMBL5608	Q16288	NT-3 growth factor receptor	87.21%	95.89%
CHEMBL1293249	Q13887	Kruppel-like factor 5	86.92%	86.33%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	86.37%	95.56%
CHEMBL2996	Q05655	Protein kinase C delta	85.42%	97.79%
CHEMBL5255	O00206	Toll-like receptor 4	85.03%	92.50%
CHEMBL3713062	P10646	Tissue factor pathway inhibitor	84.70%	97.33%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	84.39%	94.33%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	84.34%	99.23%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	83.39%	92.62%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	83.22%	86.92%
CHEMBL4051	P13569	Cystic fibrosis transmembrane conductance regulator	82.76%	95.71%
CHEMBL1871	P10275	Androgen Receptor	82.27%	96.43%
CHEMBL5028	O14672	ADAM10	80.51%	97.50%
CHEMBL3880	P07900	Heat shock protein HSP 90-alpha	80.00%	96.21%

Plants that contains it

• Vincetoxicum forrestii

Cross-Links

• PubChem: 21574532
• LOTUS: LTS0273633
• wikiData: Q105232827