4-[(6-O-beta-arabinopyranosyl-beta-glucopyranoside)oxy]-5-methoxycoumarin - Compound Card

4-[(6-O-beta-arabinopyranosyl-beta-glucopyranoside)oxy]-5-methoxycoumarin

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4-[(6-O-beta-arabinopyranosyl-beta-glucopyranoside)oxy]-5-methoxycoumarin

Structure
Zoomed Structure
  • Family: Plantae - Ebenaceae
  • Kingdom: Plantae
  • Class: Coumarin
    • Subclass: Coumarin Glycoside Derivative
Canonical Smiles O=c1cc(OC2O[C@@H](CO[C@H]3OC[C@@H]([C@@H]([C@H]3O)O)O)[C@@H]([C@H]([C@@H]2O)O)O)c2c(o1)cccc2C
InChI InChI=1S/C21H26O12/c1-8-3-2-4-10-14(8)11(5-13(23)31-10)32-21-19(28)17(26)16(25)12(33-21)7-30-20-18(27)15(24)9(22)6-29-20/h2-5,9,12,15-22,24-28H,6-7H2,1H3/t9-,12-,15-,16-,17+,18+,19-,20+,21?/m0/s1
InChIKey BIOMAEOUQPJBKL-RJDPYCFVSA-N
Formula C21H26O12
HBA 12
HBD 6
MW 470.43
Rotatable Bonds 5
TPSA 188.51
LogP -2.26
Number Rings 4
Number Aromatic Rings 2
Heavy Atom Count 33
Formal Charge 0
Fraction CSP3 0.57
Exact Mass 470.14
Number of Lipinski Rule Violations 2
# Species Family Kingdom NCBI Taxonomy ID
1 Diospyros bipindensis Ebenaceae Plantae 413723

Showing of synonyms

  • Cesari I, Queiroz EF, et al. (2013). Extensive phytochemical investigation of the polar constituents of Diospyros bipindensis Gürke traditionally used by Baka pygmies.. Phytochemistry,2013, 96, 279-287. [View] [PubMed]

No compound-protein relationship available.

Structure

SMILES: O1CCCCC1OCC2CCCC(O2)Oc3cc(=O)oc(c34)cccc4

Level: 2

Mol. Weight: 470.43 g/mol

Structure

SMILES: c1cccc(c12)oc(=O)cc2OC3CCCCO3

Level: 1

Mol. Weight: 470.43 g/mol

Structure

SMILES: O1CCCCC1COC2CCCCO2

Level: 1

Mol. Weight: 470.43 g/mol

Structure

SMILES: c1cccc(c12)oc(=O)cc2

Level: 0

Mol. Weight: 470.43 g/mol

Structure

SMILES: C1CCOCC1

Level: 0

Mol. Weight: 470.43 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-6.1
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Non-Absorbed
Madin-Darby Canine Kidney
-5.14
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-0.88

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
0.97
Plasma Protein Binding
70.97
Steady State Volume of Distribution
-

Metabolism

Breast Cancer Resistance Protein
Non-Inhibitor
CYP 1A2 Inhibitor
Non-Inhibitor
CYP 1A2 Substrate
Non-Substrate
CYP 2C19 Inhibitor
Non-Inhibitor
CYP 2C19 Substrate
Non-Substrate
CYP 2C9 Inhibitor
Non-Inhibitor
CYP 2C9 Substrate
Non-Substrate
CYP 2D6 Inhibitor
Non-Inhibitor
CYP 2D6 Substrate
Non-Substrate
CYP 3A4 Inhibitor
Non-Inhibitor
CYP 3A4 Substrate
Non-Substrate
OATP1B1
Non-Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
3.97
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-3.12
Biodegradation
Toxic
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.95
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
5.02
Micronucleos
Toxic
NR-AhR
Safe
NR-AR
Safe
NR-AR-LBD
Safe
NR-Aromatase
Safe
NR-ER
Safe
NR-ER-LBD
Safe
NR-GR
Safe
NR-PPAR-gamma
Safe
NR-TR
Safe
T. Pyriformis
-120.44
Rat (Acute)
2.41
Rat (Chronic Oral)
3.71
Fathead Minnow
3.73
Respiratory Disease
Safe
Skin Sensitisation
Toxic
SR-ARE
Safe
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Safe

General Properties

Boiling Point
566.17
Hydration Free Energy
-3.49
Log(D) at pH=7.4
-0.06
Log(P)
-1.49
Log S
-1.93
Log(Vapor Pressure)
-15.73
Melting Point
183.42
pKa Acid
4.1
pKa Basic
5.34
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Carminomycin 4-O-methyltransferase DnrK Q06528 DNRK_STRPE Streptomyces peucetius 3 0.9728
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.9415
Fatty acid-binding protein, liver P80226 FABPL_CHICK Gallus gallus 3 0.8424
Disks large homolog 1 Q12959 DLG1_HUMAN Homo sapiens 4 0.8182
Mycocyclosin synthase P9WPP7 CP121_MYCTU Mycobacterium tuberculosis 2 0.8176
Lysozyme C II P11941 LYSC2_ONCMY Oncorhynchus mykiss 3 0.8135
NAD-capped RNA hydrolase NudC P32664 NUDC_ECOLI Escherichia coli 3 0.8046
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 3 0.7898
Cytochrome P450 Q93H81 Q93H81_STRAX Streptomyces avermitilis 3 0.7634
Glutathione S-transferase P P09211 GSTP1_HUMAN Homo sapiens 2 0.7589
Lactoperoxidase P80025 PERL_BOVIN Bos taurus 3 0.7576
Methionine aminopeptidase P0AE18 MAP1_ECOLI Escherichia coli 3 0.7401
Metallo-beta-lactamase type 2 C7C422 BLAN1_KLEPN Klebsiella pneumoniae 2 0.7384
Non-receptor tyrosine-protein kinase TYK2 P29597 TYK2_HUMAN Homo sapiens 3 0.7341
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7320
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 3 0.7319
Mitochondrial poly(A) polymerase F1NBW0 F1NBW0_CHICK Gallus gallus 2 0.7303
Glutamate receptor 2 P19491 GRIA2_RAT Rattus norvegicus 2 0.7283
Cyclin-dependent kinase 9 P50750 CDK9_HUMAN Homo sapiens 3 0.7265
Aldo-keto reductase family 1 member B1 P15121 ALDR_HUMAN Homo sapiens 2 0.7244
Glutamate receptor 2 P19491 GRIA2_RAT Rattus norvegicus 2 0.7222
1-deoxy-D-xylulose 5-phosphate reductoisomerase P45568 DXR_ECOLI Escherichia coli 2 0.7211
D-aminoacyl-tRNA deacylase Q8IIS0 DTD_PLAF7 Plasmodium falciparum 2 0.7101

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