(1S,4aS,5S,7aS)-7-(acetyloxymethyl)-5-hydroxy-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: 694002a9-ab80-4c32-93bb-120170ef3b84
• Taxonomy: Organic oxygen compounds > Organooxygen compounds > Carbohydrates and carbohydrate conjugates > Monosaccharides > Hexoses
• IUPAC Name: (1S,4aS,5S,7aS)-7-(acetyloxymethyl)-5-hydroxy-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): CC(=O)OCC1=CC(C2C1C(OC=C2C(=O)O)OC3C(OC(C(C3O)O)O)CO)O
• SMILES (Isomeric): CC(=O)OCC1=C[C@@H]([C@H]2[C@@H]1[C@@H](OC=C2C(=O)O)O[C@H]3[C@@H](O[C@@H]([C@H]([C@@H]3O)O)O)CO)O
• InChI: InChI=1S/C18H24O12/c1-6(20)27-4-7-2-9(21)12-8(16(24)25)5-28-18(11(7)12)30-15-10(3-19)29-17(26)14(23)13(15)22/h2,5,9-15,17-19,21-23,26H,3-4H2,1H3,(H,24,25)/t9-,10-,11+,12-,13-,14-,15-,17-,18-/m0/s1
• InChI Key: CYAQMLMTRMBJTQ-XHVJKHTDSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₈H₂₄O₁₂
• Molecular Weight: 432.40 g/mol
• Exact Mass: 432.12677620 g/mol
• Topological Polar Surface Area (TPSA): 192.00 Ų
• XlogP: -3.80
• Atomic LogP (AlogP): -2.78
• H-Bond Acceptor: 11
• H-Bond Donor: 6
• Rotatable Bonds: 6

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.4749	47.49%
Caco-2	-	0.8996	89.96%
Blood Brain Barrier	-	0.5750	57.50%
Human oral bioavailability	-	0.7286	72.86%
Subcellular localzation	Mitochondria	0.7019	70.19%
OATP2B1 inhibitior	-	0.8545	85.45%
OATP1B1 inhibitior	+	0.7557	75.57%
OATP1B3 inhibitior	+	0.9623	96.23%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.9000	90.00%
BSEP inhibitior	-	0.8129	81.29%
P-glycoprotein inhibitior	-	0.8429	84.29%
P-glycoprotein substrate	-	0.8020	80.20%
CYP3A4 substrate	+	0.5642	56.42%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8833	88.33%
CYP3A4 inhibition	-	0.9470	94.70%
CYP2C9 inhibition	-	0.8894	88.94%
CYP2C19 inhibition	-	0.8643	86.43%
CYP2D6 inhibition	-	0.9108	91.08%
CYP1A2 inhibition	-	0.8589	85.89%
CYP2C8 inhibition	-	0.6969	69.69%
CYP inhibitory promiscuity	-	0.7524	75.24%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.6864	68.64%
Eye corrosion	-	0.9871	98.71%
Eye irritation	-	0.9244	92.44%
Skin irritation	-	0.7520	75.20%
Skin corrosion	-	0.9393	93.93%
Ames mutagenesis	-	0.7100	71.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.6036	60.36%
Micronuclear	-	0.6641	66.41%
Hepatotoxicity	-	0.6966	69.66%
skin sensitisation	-	0.8789	87.89%
Respiratory toxicity	-	0.5444	54.44%
Reproductive toxicity	+	0.7000	70.00%
Mitochondrial toxicity	+	0.6000	60.00%
Nephrotoxicity	+	0.7867	78.67%
Acute Oral Toxicity (c)	III	0.4762	47.62%
Estrogen receptor binding	+	0.5952	59.52%
Androgen receptor binding	+	0.5586	55.86%
Thyroid receptor binding	-	0.6329	63.29%
Glucocorticoid receptor binding	-	0.6530	65.30%
Aromatase binding	+	0.5434	54.34%
PPAR gamma	+	0.5219	52.19%
Honey bee toxicity	-	0.7177	71.77%
Biodegradation	-	0.7250	72.50%
Crustacea aquatic toxicity	-	0.7000	70.00%
Fish aquatic toxicity	+	0.7472	74.72%

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	96.84%	96.09%
CHEMBL3060	Q9Y345	Glycine transporter 2	90.75%	99.17%
CHEMBL3401	O75469	Pregnane X receptor	89.07%	94.73%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	88.66%	91.11%
CHEMBL2581	P07339	Cathepsin D	85.89%	98.95%
CHEMBL1806	P11388	DNA topoisomerase II alpha	84.58%	89.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	83.15%	86.33%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	82.41%	95.56%

Plants that contains it

• Morinda citrifolia

Cross-Links

• PubChem: 163021694
• LOTUS: LTS0228665
• wikiData: Q104972217