(1S,4aS,5S,7aS)-5-hydroxy-7-(hydroxymethyl)-1-[(2S,3R,4S,5S,6S)-4,5,6-trihydroxy-2-(hydroxymethyl)oxan-3-yl]oxy-1,4a,5,7a-tetrahydrocyclopenta[c]pyran-4-carboxylic acid

Details

• Internal ID: 2bfc326c-41f4-438a-986d-4c31e23020a4
• Taxonomy: Organic oxygen compounds > Organooxygen compounds > Carbohydrates and carbohydrate conjugates > Monosaccharides > Hexoses
• IUPAC Name: (1S,4aS,5S,7aS)-5-hydroxy-7-(hydroxymethyl)-1-[(2S,3R,4S,5S,6S)-4,5,6-trihydroxy-2-(hydroxymethyl)oxan-3-yl]oxy-1,4a,5,7a-tetrahydrocyclopenta[c]pyran-4-carboxylic acid
• SMILES (Canonical): C1=C(C2C(C1O)C(=COC2OC3C(OC(C(C3O)O)O)CO)C(=O)O)CO
• SMILES (Isomeric): C1=C([C@@H]2[C@H]([C@H]1O)C(=CO[C@H]2O[C@H]3[C@@H](O[C@@H]([C@H]([C@@H]3O)O)O)CO)C(=O)O)CO
• InChI: InChI=1S/C16H22O11/c17-2-5-1-7(19)10-6(14(22)23)4-25-16(9(5)10)27-13-8(3-18)26-15(24)12(21)11(13)20/h1,4,7-13,15-21,24H,2-3H2,(H,22,23)/t7-,8-,9+,10-,11-,12-,13-,15-,16-/m0/s1
• InChI Key: FAVCXKNCYCJJAL-LMXVSGMGSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₆H₂₂O₁₁
• Molecular Weight: 390.34 g/mol
• Exact Mass: 390.11621151 g/mol
• Topological Polar Surface Area (TPSA): 186.00 Ų
• XlogP: -4.30
• Atomic LogP (AlogP): -3.35
• H-Bond Acceptor: 10
• H-Bond Donor: 7
• Rotatable Bonds: 5

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.5571	55.71%
Caco-2	-	0.9016	90.16%
Blood Brain Barrier	-	0.5000	50.00%
Human oral bioavailability	-	0.6143	61.43%
Subcellular localzation	Mitochondria	0.6519	65.19%
OATP2B1 inhibitior	-	0.8569	85.69%
OATP1B1 inhibitior	+	0.7707	77.07%
OATP1B3 inhibitior	+	0.9578	95.78%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.9750	97.50%
BSEP inhibitior	-	0.9444	94.44%
P-glycoprotein inhibitior	-	0.8970	89.70%
P-glycoprotein substrate	-	0.8680	86.80%
CYP3A4 substrate	-	0.5000	50.00%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8737	87.37%
CYP3A4 inhibition	-	0.9063	90.63%
CYP2C9 inhibition	-	0.9114	91.14%
CYP2C19 inhibition	-	0.8248	82.48%
CYP2D6 inhibition	-	0.8702	87.02%
CYP1A2 inhibition	-	0.8658	86.58%
CYP2C8 inhibition	-	0.7966	79.66%
CYP inhibitory promiscuity	-	0.6442	64.42%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.6800	68.00%
Eye corrosion	-	0.9864	98.64%
Eye irritation	-	0.8878	88.78%
Skin irritation	-	0.7940	79.40%
Skin corrosion	-	0.9539	95.39%
Ames mutagenesis	-	0.6200	62.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.6840	68.40%
Micronuclear	-	0.6841	68.41%
Hepatotoxicity	-	0.6555	65.55%
skin sensitisation	-	0.8620	86.20%
Respiratory toxicity	+	0.5556	55.56%
Reproductive toxicity	+	0.6222	62.22%
Mitochondrial toxicity	+	0.5500	55.00%
Nephrotoxicity	+	0.5670	56.70%
Acute Oral Toxicity (c)	IV	0.3983	39.83%
Estrogen receptor binding	-	0.5736	57.36%
Androgen receptor binding	-	0.5000	50.00%
Thyroid receptor binding	-	0.5593	55.93%
Glucocorticoid receptor binding	-	0.6493	64.93%
Aromatase binding	+	0.7134	71.34%
PPAR gamma	+	0.6121	61.21%
Honey bee toxicity	-	0.7099	70.99%
Biodegradation	-	0.6750	67.50%
Crustacea aquatic toxicity	-	0.6600	66.00%
Fish aquatic toxicity	-	0.5000	50.00%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	93.03%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	90.44%	91.11%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	88.62%	86.92%
CHEMBL3401	O75469	Pregnane X receptor	82.88%	94.73%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	82.16%	95.56%
CHEMBL3060	Q9Y345	Glycine transporter 2	81.86%	99.17%
CHEMBL1811	P34995	Prostanoid EP1 receptor	81.42%	95.71%
CHEMBL1966	Q02127	Dihydroorotate dehydrogenase	80.06%	96.09%

Plants that contains it

• Morinda citrifolia

Cross-Links

• PubChem: 163086943
• LOTUS: LTS0070001
• wikiData: Q104992455