(1R,4aS,6S,7aS)-1-[(2S,3R,4S,5S,6R)-3-[(2S,3R,4R)-3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]-6-hydroxy-7-methylidene-4a,5,6,7a-tetrahydro-1H-cyclopenta[c]pyran-4-carboxylic acid

Details

• Internal ID: cfae4e22-36d7-4417-8fc1-6c04d12fd71b
• Taxonomy: Organic oxygen compounds > Organooxygen compounds > Carbohydrates and carbohydrate conjugates > Glycosyl compounds > O-glycosyl compounds
• IUPAC Name: (1R,4aS,6S,7aS)-1-[(2S,3R,4S,5S,6R)-3-[(2S,3R,4R)-3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]-6-hydroxy-7-methylidene-4a,5,6,7a-tetrahydro-1H-cyclopenta[c]pyran-4-carboxylic acid
• SMILES (Canonical): C=C1C(CC2C1C(OC=C2C(=O)O)C3C(C(C(C(O3)CO)O)O)OC4C(C(CO4)(CO)O)O)O
• SMILES (Isomeric): C=C1[C@H](C[C@H]2[C@@H]1[C@@H](OC=C2C(=O)O)[C@H]3[C@@H]([C@H]([C@@H]([C@H](O3)CO)O)O)O[C@H]4[C@@H]([C@](CO4)(CO)O)O)O
• InChI: InChI=1S/C21H30O13/c1-7-10(24)2-8-9(19(28)29)4-31-15(12(7)8)17-16(14(26)13(25)11(3-22)33-17)34-20-18(27)21(30,5-23)6-32-20/h4,8,10-18,20,22-27,30H,1-3,5-6H2,(H,28,29)/t8-,10+,11-,12-,13-,14+,15-,16-,17+,18+,20+,21-/m1/s1
• InChI Key: KZIXZWMZLIAKAU-URTGUFHWSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₂₁H₃₀O₁₃
• Molecular Weight: 490.50 g/mol
• Exact Mass: 490.16864101 g/mol
• Topological Polar Surface Area (TPSA): 216.00 Ų
• XlogP: -3.70
• Atomic LogP (AlogP): -3.79
• H-Bond Acceptor: 12
• H-Bond Donor: 8
• Rotatable Bonds: 6

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.6222	62.22%
Caco-2	-	0.8882	88.82%
Blood Brain Barrier	-	0.5250	52.50%
Human oral bioavailability	-	0.7857	78.57%
Subcellular localzation	Mitochondria	0.6895	68.95%
OATP2B1 inhibitior	-	0.8616	86.16%
OATP1B1 inhibitior	+	0.7950	79.50%
OATP1B3 inhibitior	+	0.9476	94.76%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.9250	92.50%
BSEP inhibitior	-	0.8532	85.32%
P-glycoprotein inhibitior	-	0.7547	75.47%
P-glycoprotein substrate	-	0.7168	71.68%
CYP3A4 substrate	+	0.6414	64.14%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8770	87.70%
CYP3A4 inhibition	-	0.8837	88.37%
CYP2C9 inhibition	-	0.8866	88.66%
CYP2C19 inhibition	-	0.8191	81.91%
CYP2D6 inhibition	-	0.8963	89.63%
CYP1A2 inhibition	-	0.8970	89.70%
CYP2C8 inhibition	+	0.4612	46.12%
CYP inhibitory promiscuity	-	0.8019	80.19%
UGT catelyzed	-	0.6000	60.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.6514	65.14%
Eye corrosion	-	0.9867	98.67%
Eye irritation	-	0.9288	92.88%
Skin irritation	-	0.7608	76.08%
Skin corrosion	-	0.9385	93.85%
Ames mutagenesis	-	0.5700	57.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4489	44.89%
Micronuclear	-	0.6641	66.41%
Hepatotoxicity	-	0.6839	68.39%
skin sensitisation	-	0.8406	84.06%
Respiratory toxicity	+	0.6222	62.22%
Reproductive toxicity	+	0.8222	82.22%
Mitochondrial toxicity	+	0.5625	56.25%
Nephrotoxicity	+	0.7018	70.18%
Acute Oral Toxicity (c)	III	0.4125	41.25%
Estrogen receptor binding	+	0.7506	75.06%
Androgen receptor binding	+	0.6211	62.11%
Thyroid receptor binding	-	0.5131	51.31%
Glucocorticoid receptor binding	-	0.5061	50.61%
Aromatase binding	+	0.7649	76.49%
PPAR gamma	+	0.6846	68.46%
Honey bee toxicity	-	0.7010	70.10%
Biodegradation	-	0.7250	72.50%
Crustacea aquatic toxicity	-	0.6500	65.00%
Fish aquatic toxicity	+	0.7200	72.00%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL221	P23219	Cyclooxygenase-1	95.55%	90.17%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	95.11%	91.11%
CHEMBL3137262	O60341	LSD1/CoREST complex	93.06%	97.09%
CHEMBL226	P30542	Adenosine A1 receptor	89.83%	95.93%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	88.85%	96.09%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	87.30%	95.56%
CHEMBL218	P21554	Cannabinoid CB1 receptor	86.78%	96.61%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	86.35%	86.92%
CHEMBL1806	P11388	DNA topoisomerase II alpha	84.41%	89.00%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	83.97%	96.95%
CHEMBL340	P08684	Cytochrome P450 3A4	83.82%	91.19%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	83.40%	96.00%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	83.29%	99.23%
CHEMBL1811	P34995	Prostanoid EP1 receptor	82.96%	95.71%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	82.71%	94.33%
CHEMBL4227	P25090	Lipoxin A4 receptor	81.23%	100.00%
CHEMBL4657	Q6V1X1	Dipeptidyl peptidase VIII	81.21%	97.21%

Plants that contains it

• Recordia reitzii

Cross-Links

• PubChem: 100927423
• LOTUS: LTS0080813
• wikiData: Q105148181