(1S)-1,5-anhydro-2-O-(6-deoxy-beta-L-mannopyranosyl)-1-[5,7-dihydroxy-2-(4-hydroxyphenyl)-4-oxo-4H-chromen-8-yl]-D-glucitol

Details

• Internal ID: 1ccfa32d-042b-4fd8-9bcd-c3193f910ce0
• Taxonomy: Phenylpropanoids and polyketides > Flavonoids > Flavonoid glycosides > Flavonoid C-glycosides > Flavonoid 8-C-glycosides
• IUPAC Name: 8-[(2S,3R,4S,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-[(2R,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyoxan-2-yl]-5,7-dihydroxy-2-(4-hydroxyphenyl)chromen-4-one
• SMILES (Canonical): CC1C(C(C(C(O1)OC2C(C(C(OC2C3=C(C=C(C4=C3OC(=CC4=O)C5=CC=C(C=C5)O)O)O)CO)O)O)O)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]([C@H](O[C@H]2C3=C(C=C(C4=C3OC(=CC4=O)C5=CC=C(C=C5)O)O)O)CO)O)O)O)O)O
• InChI: InChI=1S/C27H30O14/c1-9-19(33)21(35)23(37)27(38-9)41-26-22(36)20(34)16(8-28)40-25(26)18-13(31)6-12(30)17-14(32)7-15(39-24(17)18)10-2-4-11(29)5-3-10/h2-7,9,16,19-23,25-31,33-37H,8H2,1H3/t9-,16+,19-,20+,21+,22-,23+,25-,26+,27+/m0/s1
• InChI Key: LYGPBZVKGHHTIE-JZUNINQASA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₂₇H₃₀O₁₄
• Molecular Weight: 578.50 g/mol
• Exact Mass: 578.16355563 g/mol
• Topological Polar Surface Area (TPSA): 236.00 Ų
• XlogP: -0.90
• Atomic LogP (AlogP): -1.06
• H-Bond Acceptor: 14
• H-Bond Donor: 9
• Rotatable Bonds: 5

Synonyms

• CHEBI:82682
• Q27156205
• (1S)-1,5-anhydro-2-O-(6-deoxy-beta-L-mannopyranosyl)-1-[5,7-dihydroxy-2-(4-hydroxyphenyl)-4-oxo-4H-chromen-8-yl]-D-glucitol
• (1S)-1,5-anhydro-2-O-(beta-L-rhamnopyranosyl)-1-[5,7-dihydroxy-2-(4-hydroxyphenyl)-4-oxo-4H-chromen-8-yl]-D-glucitol

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.4777	47.77%
Caco-2	-	0.9158	91.58%
Blood Brain Barrier	-	0.8250	82.50%
Human oral bioavailability	-	0.9000	90.00%
Subcellular localzation	Mitochondria	0.6881	68.81%
OATP2B1 inhibitior	-	0.5605	56.05%
OATP1B1 inhibitior	+	0.8537	85.37%
OATP1B3 inhibitior	+	0.9552	95.52%
MATE1 inhibitior	-	0.9200	92.00%
OCT2 inhibitior	-	0.7750	77.50%
BSEP inhibitior	+	0.8531	85.31%
P-glycoprotein inhibitior	-	0.6468	64.68%
P-glycoprotein substrate	-	0.5974	59.74%
CYP3A4 substrate	+	0.6354	63.54%
CYP2C9 substrate	-	0.6795	67.95%
CYP2D6 substrate	-	0.8609	86.09%
CYP3A4 inhibition	-	0.9358	93.58%
CYP2C9 inhibition	-	0.9271	92.71%
CYP2C19 inhibition	-	0.9330	93.30%
CYP2D6 inhibition	-	0.9643	96.43%
CYP1A2 inhibition	-	0.8830	88.30%
CYP2C8 inhibition	+	0.6783	67.83%
CYP inhibitory promiscuity	-	0.7188	71.88%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.7023	70.23%
Eye corrosion	-	0.9927	99.27%
Eye irritation	-	0.9152	91.52%
Skin irritation	-	0.8192	81.92%
Skin corrosion	-	0.9626	96.26%
Ames mutagenesis	-	0.5001	50.01%
Human Ether-a-go-go-Related Gene inhibition	+	0.6443	64.43%
Micronuclear	+	0.6433	64.33%
Hepatotoxicity	-	0.8750	87.50%
skin sensitisation	-	0.9312	93.12%
Respiratory toxicity	+	0.5333	53.33%
Reproductive toxicity	+	0.7333	73.33%
Mitochondrial toxicity	-	0.5250	52.50%
Nephrotoxicity	-	0.8009	80.09%
Acute Oral Toxicity (c)	III	0.5734	57.34%
Estrogen receptor binding	+	0.8119	81.19%
Androgen receptor binding	+	0.7434	74.34%
Thyroid receptor binding	+	0.5724	57.24%
Glucocorticoid receptor binding	+	0.6478	64.78%
Aromatase binding	+	0.6205	62.05%
PPAR gamma	+	0.7244	72.44%
Honey bee toxicity	-	0.7061	70.61%
Biodegradation	-	0.7250	72.50%
Crustacea aquatic toxicity	-	0.5400	54.00%
Fish aquatic toxicity	+	0.8289	82.89%

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	99.17%	91.11%
CHEMBL2581	P07339	Cathepsin D	98.32%	98.95%
CHEMBL1951	P21397	Monoamine oxidase A	96.22%	91.49%
CHEMBL1806	P11388	DNA topoisomerase II alpha	95.76%	89.00%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	95.58%	94.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	94.14%	86.33%
CHEMBL3401	O75469	Pregnane X receptor	91.54%	94.73%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	90.46%	95.56%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	89.09%	86.92%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	87.09%	99.15%
CHEMBL3038469	P24941	CDK2/Cyclin A	85.59%	91.38%
CHEMBL3060	Q9Y345	Glycine transporter 2	84.95%	99.17%
CHEMBL2288	Q13526	Peptidyl-prolyl cis-trans isomerase NIMA-interacting 1	84.31%	91.71%
CHEMBL3880	P07900	Heat shock protein HSP 90-alpha	83.47%	96.21%
CHEMBL242	Q92731	Estrogen receptor beta	83.32%	98.35%
CHEMBL3714130	P46095	G-protein coupled receptor 6	81.45%	97.36%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	80.73%	95.89%
CHEMBL3137262	O60341	LSD1/CoREST complex	80.27%	97.09%

Plants that contains it

• Afrocarpus gracilior
• Agave xylonacantha
• Anthemis cretica
• Antiphiona pinnatisecta
• Calophyllum inophyllum
• Celtis australis
• Crataegus pinnatifida
• Crataegus sinaica
• Lycopodium japonicum
• Maackia tashiroi
• Machilus japonica
• Monoon cupulare
• Pyrrosia hastata
• Pyrrosia lingua
• Pyrrosia petiolosa
• Thelypteris esquirolii
• Turnera diffusa

Cross-Links

• PubChem: 86289611
• NPASS: NPC140154
• LOTUS: LTS0131509
• wikiData: Q27156205