Glucofrangulin A diacetate - Compound Card

Glucofrangulin A diacetate

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Glucofrangulin A diacetate

Structure
Zoomed Structure
  • Family: Plantae - Rhamnaceae
  • Kingdom: Plantae
  • Class: Quinone
    • Subclass: Anthraquinone Glycoside
Canonical Smiles OC[C@H]1O[C@@H](Oc2cc(O[C@@H]3O[C@@H](C)[C@@H]([C@H]([C@H]3OC(=O)C)OC(=O)C)O)cc3c2C(=O)c2c(C3=O)cc(cc2O)C)[C@@H]([C@H]([C@@H]1O)O)O
InChI InChI=1S/C31H34O16/c1-10-5-15-20(17(35)6-10)25(39)21-16(23(15)37)7-14(8-18(21)46-30-27(41)26(40)24(38)19(9-32)47-30)45-31-29(44-13(4)34)28(43-12(3)33)22(36)11(2)42-31/h5-8,11,19,22,24,26-32,35-36,38,40-41H,9H2,1-4H3/t11-,19+,22-,24+,26-,27+,28+,29+,30+,31-/m0/s1
InChIKey NFSJRTKXBTYHAZ-RNSHHGLOSA-N
Formula C31H34O16
HBA 16
HBD 6
MW 662.6
Rotatable Bonds 7
TPSA 245.04
LogP -1.0
Number Rings 5
Number Aromatic Rings 2
Heavy Atom Count 47
Formal Charge 0
Fraction CSP3 0.48
Exact Mass 662.18
Number of Lipinski Rule Violations 3
# Species Family Kingdom NCBI Taxonomy ID
1 Rhamnus prinoides Rhamnaceae Plantae 280022

Showing of synonyms

  • Bezabih M, Abegaz BM. (1998). Glucofrangulin A diacetate from the fruits of Rhamnus prinoides. Bulletin of the Chemical Society of Ethiopia,1998,12(1),45-48. [View] [PubMed]
Pubchem: 102404309

No compound-protein relationship available.

Structure

SMILES: c1cccc(C2=O)c1C(=O)c(c23)cc(OC4CCCCO4)cc3OC5CCCCO5

Level: 2

Mol. Weight: 662.6 g/mol

Structure

SMILES: c1cccc(C2=O)c1C(=O)c(c23)cccc3OC4CCCCO4

Level: 1

Mol. Weight: 662.6 g/mol

Structure

SMILES: c1cccc(C2=O)c1C(=O)c(c23)ccc(c3)OC4CCCCO4

Level: 1

Mol. Weight: 662.6 g/mol

Structure

SMILES: c1cccc(c12)C(=O)c3c(C2=O)cccc3

Level: 0

Mol. Weight: 662.6 g/mol

Structure

SMILES: C1CCOCC1

Level: 0

Mol. Weight: 662.6 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-6.35
Human Oral Bioavailability 20%
Non-Bioavailable
Human Intestinal Absorption
Non-Absorbed
Madin-Darby Canine Kidney
-4.900
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Inhibitor
P-Glycoprotein Substrate
Substrate
Skin Permeability
38.02

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
0.700
Plasma Protein Binding
81.81
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
Inhibitor
CYP 2D6 Substrate
Non-Substrate
CYP 3A4 Inhibitor
Non-Inhibitor
CYP 3A4 Substrate
Non-Substrate
OATP1B1
Non-Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
6.540
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-2.560
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
1.020
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
6.390
Micronucleos
Toxic
NR-AhR
Safe
NR-AR
Safe
NR-AR-LBD
Safe
NR-Aromatase
Safe
NR-ER
Safe
NR-ER-LBD
Safe
NR-GR
Toxic
NR-PPAR-gamma
Safe
NR-TR
Safe
T. Pyriformis
-70206.840
Rat (Acute)
3.110
Rat (Chronic Oral)
4.450
Fathead Minnow
104.650
Respiratory Disease
Safe
Skin Sensitisation
Safe
SR-ARE
Safe
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Safe

General Properties

Boiling Point
1793.410
Hydration Free Energy
-2.920
Log(D) at pH=7.4
0.360
Log(P)
0.95
Log S
-3.53
Log(Vapor Pressure)
-100.73
Melting Point
210.55
pKa Acid
4.68
pKa Basic
0.42
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.9029
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.9029
Fibroblast growth factor receptor 1 P11362 FGFR1_HUMAN Homo sapiens 3 0.8511
Fibroblast growth factor receptor 1 P11362 FGFR1_HUMAN Homo sapiens 3 0.8511
Cathepsin S P25774 CATS_HUMAN Homo sapiens 3 0.8262
Cathepsin S P25774 CATS_HUMAN Homo sapiens 3 0.8262
Flavin reductase (NADPH) P30043 BLVRB_HUMAN Homo sapiens 3 0.8237
Flavin reductase (NADPH) P30043 BLVRB_HUMAN Homo sapiens 3 0.8237
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8214
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8214
E3 ubiquitin-protein ligase Mdm2 P56273 MDM2_XENLA Xenopus laevis 3 0.8200
E3 ubiquitin-protein ligase Mdm2 P56273 MDM2_XENLA Xenopus laevis 3 0.8200
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.8138
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.8138
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.8136
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.8136
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase F6MZ55 F6MZ55_9FIRM Sporomusa ovata 3 0.8021
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase F6MZ55 F6MZ55_9FIRM Sporomusa ovata 3 0.8021
Nuclear receptor subfamily 4immunitygroup A member 1 P22736 NR4A1_HUMAN Homo sapiens 3 0.7611
Nuclear receptor subfamily 4immunitygroup A member 1 P22736 NR4A1_HUMAN Homo sapiens 3 0.7611
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7391
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7391
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7359
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7359
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7293
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7293
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7245
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7245
Cytosolic purine 5'-nucleotidase P49902 5NTC_HUMAN Homo sapiens 2 0.7226
Cytosolic purine 5'-nucleotidase P49902 5NTC_HUMAN Homo sapiens 2 0.7226
Thiamine-phosphate synthase P39594 THIE_BACSU Bacillus subtilis 3 0.7194
Thiamine-phosphate synthase P39594 THIE_BACSU Bacillus subtilis 3 0.7194
Thiamine-phosphate synthase P39594 THIE_BACSU Bacillus subtilis 2 0.7133
Thiamine-phosphate synthase P39594 THIE_BACSU Bacillus subtilis 2 0.7133
Nitric oxide synthase oxygenase O34453 NOSO_BACSU Bacillus subtilis 3 0.7124
Nitric oxide synthase oxygenase O34453 NOSO_BACSU Bacillus subtilis 3 0.7124
GCN5-related N-acetyltransferase B1YEL6 B1YEL6_EXIS2 Exiguobacterium sibiricum 3 0.7051
GCN5-related N-acetyltransferase B1YEL6 B1YEL6_EXIS2 Exiguobacterium sibiricum 3 0.7051
Disks large homolog 1 Q12959 DLG1_HUMAN Homo sapiens 3 0.7015
Disks large homolog 1 Q12959 DLG1_HUMAN Homo sapiens 3 0.7015

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