Gambiriin B1

Details

• Internal ID: 803bfc05-3e8b-4d27-b2ff-8d875a025c7c
• Taxonomy: Phenylpropanoids and polyketides > Flavonoids > Flavans > Catechins
• IUPAC Name: 2-[[(2R,3S,8S,9R)-2,9-bis(3,4-dihydroxyphenyl)-3,5-dihydroxy-3,4,8,9-tetrahydro-2H-furo[2,3-h]chromen-8-yl]methyl]benzene-1,3,5-triol
• SMILES (Canonical): C1C(C(OC2=C1C(=CC3=C2C(C(O3)CC4=C(C=C(C=C4O)O)O)C5=CC(=C(C=C5)O)O)O)C6=CC(=C(C=C6)O)O)O
• SMILES (Isomeric): C1[C@@H]([C@H](OC2=C1C(=CC3=C2[C@H]([C@@H](O3)CC4=C(C=C(C=C4O)O)O)C5=CC(=C(C=C5)O)O)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)22(37)5-12)28-26(40-25)11-21(36)16-9-24(39)29(41-30(16)28)13-2-4-18(33)23(38)6-13/h1-8,11,24-25,27,29,31-39H,9-10H2/t24-,25-,27-,29+/m0/s1
• InChI Key: HLOYODWMNGTCGH-SEGPTPNXSA-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:81328
• C17775
• Q27155266
• 2-[[(2R,3S,8S,9R)-2,9-bis(3,4-dihydroxyphenyl)-3,5-dihydroxy-3,4,8,9-tetrahydro-2H-furo[2,3-h]chromen-8-yl]methyl]benzene-1,3,5-triol

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.8899	88.99%
Caco-2	-	0.8871	88.71%
Blood Brain Barrier	-	0.5750	57.50%
Human oral bioavailability	-	0.7714	77.14%
Subcellular localzation	Mitochondria	0.5933	59.33%
OATP2B1 inhibitior	-	0.5695	56.95%
OATP1B1 inhibitior	+	0.9060	90.60%
OATP1B3 inhibitior	+	0.9304	93.04%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.8750	87.50%
BSEP inhibitior	+	0.8711	87.11%
P-glycoprotein inhibitior	+	0.7036	70.36%
P-glycoprotein substrate	-	0.7630	76.30%
CYP3A4 substrate	+	0.5752	57.52%
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	+	0.7172	71.72%
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	-	0.8403	84.03%
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	+	0.9340	93.40%
Micronuclear	+	0.7918	79.18%
Hepatotoxicity	-	0.7250	72.50%
skin sensitisation	-	0.7738	77.38%
Respiratory toxicity	+	0.6889	68.89%
Reproductive toxicity	+	0.8333	83.33%
Mitochondrial toxicity	+	0.6375	63.75%
Nephrotoxicity	-	0.6993	69.93%
Acute Oral Toxicity (c)	IV	0.3814	38.14%
Estrogen receptor binding	+	0.8017	80.17%
Androgen receptor binding	+	0.7946	79.46%
Thyroid receptor binding	+	0.6479	64.79%
Glucocorticoid receptor binding	+	0.6031	60.31%
Aromatase binding	-	0.5223	52.23%
PPAR gamma	+	0.7829	78.29%
Honey bee toxicity	-	0.7794	77.94%
Biodegradation	-	0.8500	85.00%
Crustacea aquatic toxicity	+	0.5100	51.00%
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	99.54%	91.11%
CHEMBL1951	P21397	Monoamine oxidase A	96.84%	91.49%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	95.23%	96.09%
CHEMBL3137262	O60341	LSD1/CoREST complex	93.58%	97.09%
CHEMBL4040	P28482	MAP kinase ERK2	92.39%	83.82%
CHEMBL1806	P11388	DNA topoisomerase II alpha	90.12%	89.00%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	88.13%	94.45%
CHEMBL2581	P07339	Cathepsin D	87.98%	98.95%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	86.86%	99.15%
CHEMBL233	P35372	Mu opioid receptor	85.80%	97.93%
CHEMBL236	P41143	Delta opioid receptor	85.68%	99.35%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	85.13%	95.56%
CHEMBL5608	Q16288	NT-3 growth factor receptor	83.90%	95.89%
CHEMBL2535	P11166	Glucose transporter	83.66%	98.75%
CHEMBL3401	O75469	Pregnane X receptor	83.03%	94.73%
CHEMBL3004	P33527	Multidrug resistance-associated protein 1	82.00%	96.37%
CHEMBL5697	Q9GZT9	Egl nine homolog 1	81.08%	93.40%
CHEMBL1929	P47989	Xanthine dehydrogenase	80.82%	96.12%
CHEMBL1293249	Q13887	Kruppel-like factor 5	80.54%	86.33%

Plants that contains it

• Uncaria gambir

Cross-Links

• PubChem: 16203169
• NPASS: NPC268102