3,4,8,10-tetrahydroxy-2-(hydroxymethyl)-9-methoxy-3,4,4a,10b-tetrahydro-2H-pyrano[3,2-c]isochromen-6-one

Details

• Internal ID: a78584aa-e8a2-4ccf-a1e2-fc86bca4b060
• Taxonomy: Benzenoids > Benzene and substituted derivatives > Benzoic acids and derivatives > Hydroxybenzoic acid derivatives > Gallic acid and derivatives
• IUPAC Name: 3,4,8,10-tetrahydroxy-2-(hydroxymethyl)-9-methoxy-3,4,4a,10b-tetrahydro-2H-pyrano[3,2-c]isochromen-6-one
• SMILES (Canonical): COC1=C(C=C2C(=C1O)C3C(C(C(C(O3)CO)O)O)OC2=O)O
• SMILES (Isomeric): COC1=C(C=C2C(=C1O)C3C(C(C(C(O3)CO)O)O)OC2=O)O
• InChI: InChI=1S/C14H16O9/c1-21-11-5(16)2-4-7(9(11)18)12-13(23-14(4)20)10(19)8(17)6(3-15)22-12/h2,6,8,10,12-13,15-19H,3H2,1H3
• InChI Key: YWJXCIXBAKGUKZ-UHFFFAOYSA-N
• Popularity: 10 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₄H₁₆O₉
• Molecular Weight: 328.27 g/mol
• Exact Mass: 328.07943208 g/mol
• Topological Polar Surface Area (TPSA): 146.00 Ų
• XlogP: -1.00

Synonyms

• NSC383465
• Cuscutin;Corylopsin
• Prestwick0_000811
• Prestwick1_000811
• Prestwick2_000811
• Prestwick3_000811
• BSPBio_000701
• MLS006011420
• Bergenin, Bergenin monohydrate
• SCHEMBL893718
• SPBio_002622
• BPBio1_000773
• CHEMBL1619590
• CHEBI:91545
• DTXSID40859392
• YWJXCIXBAKGUKZ-UHFFFAOYSA-N
• BCP15931
• CID 2356
• ZINC00000079
• ZINC00389665
• ZINC01303449
• ZINC02048952
• AKOS005613004
• AC-8033
• NSC-383465
• SMP1_000100
• NCGC00179471-01
• LS-14297
• SMR001550645
• BRD-A15034104-002-03-6
• Q27163378
• 3,4,4a,10b-Tetrahydro-3,4,8,10-tetrahydroxy-2-(hydroxymethyl)-9-methoxypyrano[3,2-c][2]benzopyran-6H-one
• 3,4,8,10-tetrahydroxy-2-(hydroxymethyl)-9-methoxy-3,4,4a,10b-tetrahydro-2H-pyrano[3,2-c][2]benzopyran-6-one
• 3,4,8,10-Tetrahydroxy-2-(hydroxymethyl)-9-methoxy-3,4,4a,10b-tetrahydropyrano[3,2-c][2]benzopyran-6(2H)-one
• 3,4,8,10-Tetrahydroxy-2-(hydroxymethyl)-9-methoxy-3,4,4a,10b-tetrahydropyrano[3,2-c]isochromen-6(2H)-one #
• bergenin:pyrano[3,2-c][2]benzopyran-6(2h)-one,3,4,4a,10b-tetrahydro-3,4,8,10-tetrahydroxy-2-(hydroxymethyl)-9-methoxy-, [2r-(2,3,4,4a, 10b)]-,
• Pyrano[3,2-c][2]benzopyran-6(2H)-one, 3,4,4a,10b-tetrahydro-3,4,8,10-tetrahydroxy-2-(hydroxymethyl)-9-methoxy-, [2R-(2.alpha.,3.beta.,4.alpha.,4a.alpha.,10b.beta.)]-

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
No predicted properties yet!

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL1795129	P05231	Interleukin-6	208 nM	IC50	via Super-PRED

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	99.05%	91.11%
CHEMBL2581	P07339	Cathepsin D	93.18%	98.95%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	91.90%	96.09%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	90.14%	94.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	88.45%	95.56%
CHEMBL1293249	Q13887	Kruppel-like factor 5	88.31%	86.33%
CHEMBL1806	P11388	DNA topoisomerase II alpha	87.24%	89.00%
CHEMBL3060	Q9Y345	Glycine transporter 2	87.23%	99.17%
CHEMBL3401	O75469	Pregnane X receptor	86.77%	94.73%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	85.06%	86.92%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	82.23%	99.15%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	82.15%	96.00%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	81.94%	85.14%

Plants that contains it

• Actaea cimicifuga
• Ardisia japonica
• Astilbe rubra
• Astilbe thunbergii
• Bergenia stracheyi
• Brachystemma calycinum
• Dipterocarpus grandiflorus
• Flueggea virosa
• Flueggea virosa subsp. melanthesoides
• Hopea utilis
• Mallotus japonicus
• Mallotus repandus
• Peltophorum africanum
• Pulicaria wightiana
• Rodgersia podophylla
• Rodgersia sambucifolia
• Tridax procumbens
• Vatica affinis
• Vatica albiramis
• Vatica diospyroides
• Vatica pauciflora

Cross-Links

• PubChem: 2356
• LOTUS: LTS0089177
• wikiData: Q27163378