(2S)-8-[(2S,3R)-5,7-dihydroxy-2-(4-hydroxyphenyl)-4-oxo-2,3-dihydrochromen-3-yl]-2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-2,3-dihydrochromen-4-one

Details

• Internal ID: d9f147df-208a-4891-97e3-ba0884ede548
• Taxonomy: Phenylpropanoids and polyketides > Flavonoids > Biflavonoids and polyflavonoids
• IUPAC Name: (2S)-8-[(2S,3R)-5,7-dihydroxy-2-(4-hydroxyphenyl)-4-oxo-2,3-dihydrochromen-3-yl]-2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-2,3-dihydrochromen-4-one
• SMILES (Canonical): C1C(OC2=C(C(=CC(=C2C1=O)O)O)C3C(OC4=CC(=CC(=C4C3=O)O)O)C5=CC=C(C=C5)O)C6=CC(=C(C=C6)O)O
• SMILES (Isomeric): C1[C@H](OC2=C(C(=CC(=C2C1=O)O)O)[C@@H]3[C@H](OC4=CC(=CC(=C4C3=O)O)O)C5=CC=C(C=C5)O)C6=CC(=C(C=C6)O)O
• InChI: InChI=1S/C30H22O11/c31-14-4-1-12(2-5-14)29-27(28(39)25-18(35)8-15(32)9-23(25)41-29)26-20(37)10-19(36)24-21(38)11-22(40-30(24)26)13-3-6-16(33)17(34)7-13/h1-10,22,27,29,31-37H,11H2/t22-,27-,29+/m0/s1
• InChI Key: IMIXFUXOSFSXPC-DETITRACSA-N
• Popularity: 3 references in papers

Physical and Chemical Properties

• Molecular Formula: C₃₀H₂₂O₁₁
• Molecular Weight: 558.50 g/mol
• Exact Mass: 558.11621151 g/mol
• Topological Polar Surface Area (TPSA): 194.00 Ų
• XlogP: 4.20
• Atomic LogP (AlogP): 4.43
• H-Bond Acceptor: 11
• H-Bond Donor: 7
• Rotatable Bonds: 3

Synonyms

• GB 2a
• GB-2a
• CHEMBL445452
• (2S)-8-[(2S,3R)-5,7-dihydroxy-2-(4-hydroxyphenyl)-4-oxo-2,3-dihydrochromen-3-yl]-2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-2,3-dihydrochromen-4-one
• (3,8'-Bi-2H-1-benzopyran)-4,4'(3H,3'H)-dione, 2'-(3,4-dihydroxyphenyl)-5,5',7,7'-tetrahydroxy-2-(4-hydroxyphenyl)-, (2S,2'S,3R)-
• [3,8'-Bi-4H-1-benzopyran]-4,4'-dione, 2'-(3,4-dihydroxyphenyl)-2,2',3,3'-tetrahydro-5,5',7,7'-tetrahydroxy-2-(4-hydroxyphenyl)-, (2S,2'S,3R)-
• [3,8'-Bi-2H-1-benzopyran]-4,4'(3H,3'H)-dione, 2'-(3,4-dihydroxyphenyl)-5,5',7,7'-tetrahydroxy-2-(4-hydroxyphenyl)-, (2S,2'S,3R)-
• DTXSID30939798
• IMIXFUXOSFSXPC-DETITRACSA-N
• BDBM50478421
• AKOS040762681
• (2S,3R)-3-[(2S)-2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-4-oxo-chroman-8-yl]-5,7-dihydroxy-2-(4-hydroxyphenyl)chroman-4-one
• 2'-(3,4-Dihydroxyphenyl)-5,5',7,7'-tetrahydroxy-2-(4-hydroxyphenyl)-2,2',3,3'-tetrahydro-4H,4'H-[3,8'-bi-1-benzopyran]-4,4'-dione

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.6689	66.89%
Caco-2	-	0.8913	89.13%
Blood Brain Barrier	-	0.7750	77.50%
Human oral bioavailability	-	0.8000	80.00%
Subcellular localzation	Mitochondria	0.6157	61.57%
OATP2B1 inhibitior	-	0.5652	56.52%
OATP1B1 inhibitior	+	0.9049	90.49%
OATP1B3 inhibitior	+	0.9937	99.37%
MATE1 inhibitior	-	0.8400	84.00%
OCT2 inhibitior	-	0.8750	87.50%
BSEP inhibitior	+	0.7651	76.51%
P-glycoprotein inhibitior	+	0.7181	71.81%
P-glycoprotein substrate	-	0.8043	80.43%
CYP3A4 substrate	+	0.6057	60.57%
CYP2C9 substrate	-	0.8038	80.38%
CYP2D6 substrate	-	0.7623	76.23%
CYP3A4 inhibition	+	0.5441	54.41%
CYP2C9 inhibition	+	0.5693	56.93%
CYP2C19 inhibition	-	0.8218	82.18%
CYP2D6 inhibition	-	0.8649	86.49%
CYP1A2 inhibition	+	0.5087	50.87%
CYP2C8 inhibition	+	0.6773	67.73%
CYP inhibitory promiscuity	-	0.8017	80.17%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.6701	67.01%
Eye corrosion	-	0.9933	99.33%
Eye irritation	-	0.7411	74.11%
Skin irritation	-	0.6028	60.28%
Skin corrosion	-	0.9136	91.36%
Ames mutagenesis	+	0.6300	63.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.8506	85.06%
Micronuclear	+	0.8359	83.59%
Hepatotoxicity	-	0.7000	70.00%
skin sensitisation	-	0.8422	84.22%
Respiratory toxicity	+	0.5556	55.56%
Reproductive toxicity	+	0.8333	83.33%
Mitochondrial toxicity	+	0.7250	72.50%
Nephrotoxicity	+	0.7117	71.17%
Acute Oral Toxicity (c)	II	0.4739	47.39%
Estrogen receptor binding	+	0.7672	76.72%
Androgen receptor binding	+	0.7970	79.70%
Thyroid receptor binding	+	0.5533	55.33%
Glucocorticoid receptor binding	+	0.6729	67.29%
Aromatase binding	-	0.6422	64.22%
PPAR gamma	+	0.6505	65.05%
Honey bee toxicity	-	0.7744	77.44%
Biodegradation	-	0.9000	90.00%
Crustacea aquatic toxicity	-	0.5500	55.00%
Fish aquatic toxicity	+	0.8567	85.67%

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	99.38%	91.11%
CHEMBL3137262	O60341	LSD1/CoREST complex	92.91%	97.09%
CHEMBL1806	P11388	DNA topoisomerase II alpha	92.80%	89.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	92.33%	95.56%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	92.22%	99.15%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	91.71%	99.23%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	87.81%	96.09%
CHEMBL2581	P07339	Cathepsin D	87.21%	98.95%
CHEMBL1929	P47989	Xanthine dehydrogenase	87.00%	96.12%
CHEMBL4208	P20618	Proteasome component C5	86.08%	90.00%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	86.02%	94.45%
CHEMBL4040	P28482	MAP kinase ERK2	85.42%	83.82%
CHEMBL2535	P11166	Glucose transporter	83.78%	98.75%
CHEMBL2553	Q15418	Ribosomal protein S6 kinase alpha 1	81.96%	85.11%
CHEMBL3401	O75469	Pregnane X receptor	81.40%	94.73%

Plants that contains it

• Garcinia kola
• Garcinia multiflora
• Garcinia prainiana

Cross-Links

• PubChem: 176988
• NPASS: NPC224851
• LOTUS: LTS0121922
• wikiData: Q82916362