Gambiriin B3

Details

• Internal ID: c8dec63c-77c8-4928-a34b-b04a092d47ca
• Taxonomy: Phenylpropanoids and polyketides > Flavonoids > Flavans > Catechins
• IUPAC Name: 2-[[(2R,3R,6S,7R)-3,7-bis(3,4-dihydroxyphenyl)-4,6-dihydroxy-3,5,6,7-tetrahydro-2H-furo[3,2-g]chromen-2-yl]methyl]benzene-1,3,5-triol
• SMILES (Canonical): C1C(C(OC2=CC3=C(C(C(O3)CC4=C(C=C(C=C4O)O)O)C5=CC(=C(C=C5)O)O)C(=C21)O)C6=CC(=C(C=C6)O)O)O
• SMILES (Isomeric): C1[C@@H]([C@H](OC2=CC3=C([C@H]([C@H](O3)CC4=C(C=C(C=C4O)O)O)C5=CC(=C(C=C5)O)O)C(=C21)O)C6=CC(=C(C=C6)O)O)O
• InChI: InChI=1S/C30H26O11/c31-14-7-19(34)15(20(35)8-14)10-25-27(12-1-3-17(32)21(36)5-12)28-26(40-25)11-24-16(29(28)39)9-23(38)30(41-24)13-2-4-18(33)22(37)6-13/h1-8,11,23,25,27,30-39H,9-10H2/t23-,25+,27-,30+/m0/s1
• InChI Key: FFCVTFZKQFEUKL-YJRUHBOJSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₃₀H₂₆O₁₁
• Molecular Weight: 562.50 g/mol
• Exact Mass: 562.14751164 g/mol
• Topological Polar Surface Area (TPSA): 201.00 Ų
• XlogP: 3.50
• Atomic LogP (AlogP): 3.50
• H-Bond Acceptor: 11
• H-Bond Donor: 9
• Rotatable Bonds: 4

Synonyms

• CHEBI:81330
• DTXSID301101315
• C17777
• Q27155269
• 2-[[(2R,3R,6S,7R)-3,7-Bis(3,4-dihydroxyphenyl)-2,3,6,7-tetrahydro-4,6-dihydroxy-5H-furo[3,2-g][1]benzopyran-2-yl]methyl]-1,3,5-benzenetriol
• 76236-90-3

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.8899	88.99%
Caco-2	-	0.9026	90.26%
Blood Brain Barrier	-	0.5750	57.50%
Human oral bioavailability	-	0.7857	78.57%
Subcellular localzation	Mitochondria	0.5933	59.33%
OATP2B1 inhibitior	-	0.5673	56.73%
OATP1B1 inhibitior	+	0.8791	87.91%
OATP1B3 inhibitior	+	0.9304	93.04%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.8750	87.50%
BSEP inhibitior	+	0.8543	85.43%
P-glycoprotein inhibitior	+	0.7286	72.86%
P-glycoprotein substrate	-	0.7574	75.74%
CYP3A4 substrate	+	0.5660	56.60%
CYP2C9 substrate	-	0.5994	59.94%
CYP2D6 substrate	+	0.5264	52.64%
CYP3A4 inhibition	-	0.7667	76.67%
CYP2C9 inhibition	-	0.8411	84.11%
CYP2C19 inhibition	-	0.8235	82.35%
CYP2D6 inhibition	-	0.8647	86.47%
CYP1A2 inhibition	-	0.8592	85.92%
CYP2C8 inhibition	+	0.7426	74.26%
CYP inhibitory promiscuity	-	0.6604	66.04%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.9700	97.00%
Carcinogenicity (trinary)	Non-required	0.4842	48.42%
Eye corrosion	-	0.9910	99.10%
Eye irritation	-	0.8094	80.94%
Skin irritation	-	0.6648	66.48%
Skin corrosion	-	0.9373	93.73%
Ames mutagenesis	+	0.5900	59.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.9079	90.79%
Micronuclear	+	0.7918	79.18%
Hepatotoxicity	-	0.7125	71.25%
skin sensitisation	-	0.7738	77.38%
Respiratory toxicity	+	0.6778	67.78%
Reproductive toxicity	+	0.8333	83.33%
Mitochondrial toxicity	+	0.6375	63.75%
Nephrotoxicity	-	0.8475	84.75%
Acute Oral Toxicity (c)	IV	0.3814	38.14%
Estrogen receptor binding	+	0.7949	79.49%
Androgen receptor binding	+	0.7844	78.44%
Thyroid receptor binding	+	0.6226	62.26%
Glucocorticoid receptor binding	+	0.6369	63.69%
Aromatase binding	-	0.5054	50.54%
PPAR gamma	+	0.7685	76.85%
Honey bee toxicity	-	0.8337	83.37%
Biodegradation	-	0.8500	85.00%
Crustacea aquatic toxicity	-	0.5400	54.00%
Fish aquatic toxicity	+	0.7514	75.14%

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	99.70%	91.11%
CHEMBL1951	P21397	Monoamine oxidase A	98.46%	91.49%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	96.26%	96.09%
CHEMBL3137262	O60341	LSD1/CoREST complex	94.10%	97.09%
CHEMBL1806	P11388	DNA topoisomerase II alpha	90.55%	89.00%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	90.18%	99.15%
CHEMBL3004	P33527	Multidrug resistance-associated protein 1	89.83%	96.37%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	87.26%	94.45%
CHEMBL233	P35372	Mu opioid receptor	83.76%	97.93%
CHEMBL2581	P07339	Cathepsin D	82.21%	98.95%
CHEMBL5608	Q16288	NT-3 growth factor receptor	82.15%	95.89%
CHEMBL1929	P47989	Xanthine dehydrogenase	82.11%	96.12%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	82.08%	95.56%
CHEMBL5339	Q5NUL3	G-protein coupled receptor 120	81.88%	95.78%
CHEMBL2563	Q9UQL6	Histone deacetylase 5	81.54%	89.67%
CHEMBL1293249	Q13887	Kruppel-like factor 5	81.27%	86.33%
CHEMBL4208	P20618	Proteasome component C5	81.20%	90.00%

Plants that contains it

• Uncaria gambir

Cross-Links

• PubChem: 46173996
• NPASS: NPC310690