Gentesic acid 5-O-glucoside - Compound Card

Gentesic acid 5-O-glucoside

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Gentesic acid 5-O-glucoside

Structure
Zoomed Structure
  • Family: Plantae - Anacardiaceae
  • Kingdom: Plantae
  • Class: Phenolic
Canonical Smiles OC[C@H]1OC(Oc2ccc(c(c2)C(=O)O)O)[C@@H]([C@H]([C@@H]1O)O)O
InChI InChI=1S/C13H16O9/c14-4-8-9(16)10(17)11(18)13(22-8)21-5-1-2-7(15)6(3-5)12(19)20/h1-3,8-11,13-18H,4H2,(H,19,20)/t8-,9-,10+,11-,13?/m1/s1
InChIKey CBTFERBMQQAROP-TWEVDUBQSA-N
Formula C13H16O9
HBA 8
HBD 6
MW 316.26
Rotatable Bonds 4
TPSA 156.91
LogP -1.73
Number Rings 2
Number Aromatic Rings 1
Heavy Atom Count 22
Formal Charge 0
Fraction CSP3 0.46
Exact Mass 316.08
Number of Lipinski Rule Violations 1
# Species Family Kingdom NCBI Taxonomy ID
1 Harpephyllum caffrum Anacardiaceae Plantae 289712

Showing of synonyms

  • Nawwar M, Hussein S, et al. (2011). Constitutive phenolics of Harpephyllum caffrum (Anacardiaceae) and their biological effects on human keratinocytes. Fitoterapia,2011,82(8),1265-1271. [View] [PubMed]
Pubchem: 163075272
Nmrshiftdb2: 60028408

No compound-protein relationship available.

Structure

SMILES: c1ccccc1OC2CCCCO2

Level: 1

Mol. Weight: 316.26 g/mol

Structure

SMILES: C1CCOCC1

Level: 0

Mol. Weight: 316.26 g/mol

Structure

SMILES: c1ccccc1

Level: 0

Mol. Weight: 316.26 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-5.96
Human Oral Bioavailability 20%
Non-Bioavailable
Human Intestinal Absorption
Non-Absorbed
Madin-Darby Canine Kidney
-5.46
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-1.72

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
0.53
Plasma Protein Binding
48.86
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
5.6
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-1.74
Biodegradation
Toxic
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
1.1
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
3.21
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
-2.15
Rat (Acute)
1.81
Rat (Chronic Oral)
3.88
Fathead Minnow
3.49
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
465.97
Hydration Free Energy
-15.94
Log(D) at pH=7.4
-2.98
Log(P)
-0.34
Log S
-1.54
Log(Vapor Pressure)
-10.93
Melting Point
181.51
pKa Acid
3.12
pKa Basic
5.02
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Glucan 1,3-beta-glucosidase P29717 EXG1_CANAL Candida albicans 3 0.9017
Glucan 1,3-beta-glucosidase P29717 EXG1_CANAL Candida albicans 3 0.9017
Serine/threonine-protein kinase pim-1 P11309 PIM1_HUMAN Homo sapiens 3 0.8862
Serine/threonine-protein kinase pim-1 P11309 PIM1_HUMAN Homo sapiens 3 0.8862
Flavin-dependent monooxygenase Q93L51 TETX_BACT4 Bacteroides thetaiotaomicron 3 0.8815
Flavin-dependent monooxygenase Q93L51 TETX_BACT4 Bacteroides thetaiotaomicron 3 0.8815
NAD-capped RNA hydrolase NudC P32664 NUDC_ECOLI Escherichia coli 3 0.8745
NAD-capped RNA hydrolase NudC P32664 NUDC_ECOLI Escherichia coli 3 0.8745
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.8604
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.8604
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.8564
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.8564
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 3 0.8429
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 3 0.8429
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.8425
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.8425
Glucan 1,3-beta-glucosidase P29717 EXG1_CANAL Candida albicans 3 0.8073
Glucan 1,3-beta-glucosidase P29717 EXG1_CANAL Candida albicans 3 0.8073
Acidic phospholipase A2 3 P60045 PA2A3_NAJSG Naja sagittifera 3 0.7980
Acidic phospholipase A2 3 P60045 PA2A3_NAJSG Naja sagittifera 3 0.7980
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7923
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7923
Tyrosine-protein kinase JAK3 P52333 JAK3_HUMAN Homo sapiens 3 0.7838
Tyrosine-protein kinase JAK3 P52333 JAK3_HUMAN Homo sapiens 3 0.7838
Deacetoxycephalosporin C synthase P18548 CEFE_STRCL Streptomyces clavuligerus 3 0.7685
Deacetoxycephalosporin C synthase P18548 CEFE_STRCL Streptomyces clavuligerus 3 0.7685
5-methylthioadenosine/S-adenosylhomocysteine deaminase Q7NZ90 Q7NZ90_CHRVO Chromobacterium violaceum 3 0.7663
5-methylthioadenosine/S-adenosylhomocysteine deaminase Q7NZ90 Q7NZ90_CHRVO Chromobacterium violaceum 3 0.7663
Mitogen-activated protein kinase 8 P45983 MK08_HUMAN Homo sapiens 3 0.7532
Mitogen-activated protein kinase 8 P45983 MK08_HUMAN Homo sapiens 3 0.7532
2',3'-cyclic-nucleotide 3'-phosphodiesterase P16330 CN37_MOUSE Mus musculus 3 0.7500
2',3'-cyclic-nucleotide 3'-phosphodiesterase P16330 CN37_MOUSE Mus musculus 3 0.7500
Kynurenine/alpha-aminoadipate aminotransferase, mitochondrial Q8N5Z0 AADAT_HUMAN Homo sapiens 2 0.7450
Kynurenine/alpha-aminoadipate aminotransferase, mitochondrial Q8N5Z0 AADAT_HUMAN Homo sapiens 2 0.7450
Carbonic anhydrase 1 P00915 CAH1_HUMAN Homo sapiens 3 0.7393
Carbonic anhydrase 1 P00915 CAH1_HUMAN Homo sapiens 3 0.7393
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7384
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7384
DNA-directed DNA polymerase Q38087 DPOL_BPR69 Escherichia phage RB69 3 0.7377
DNA-directed DNA polymerase Q38087 DPOL_BPR69 Escherichia phage RB69 3 0.7377
DNA gyrase subunit A P0AES5 GYRA_SHIFL Shigella flexneri 3 0.7373
DNA gyrase subunit A P0AES5 GYRA_SHIFL Shigella flexneri 3 0.7373
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase Q9TQS6 DHDH_MACFA Macaca fascicularis 3 0.7353
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase Q9TQS6 DHDH_MACFA Macaca fascicularis 3 0.7353
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7351
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7351
N-acetyltransferase domain-containing protein Q9HV14 Q9HV14_PSEAE Pseudomonas aeruginosa 3 0.7229
N-acetyltransferase domain-containing protein Q9HV14 Q9HV14_PSEAE Pseudomonas aeruginosa 3 0.7229
Alpha-ketoglutarate-dependent dioxygenase FTO Q9C0B1 FTO_HUMAN Homo sapiens 2 0.7208
Alpha-ketoglutarate-dependent dioxygenase FTO Q9C0B1 FTO_HUMAN Homo sapiens 2 0.7208
Aurora kinase A O14965 AURKA_HUMAN Homo sapiens 3 0.7113
Aurora kinase A O14965 AURKA_HUMAN Homo sapiens 3 0.7113
Trichothecene 15-O-acetyltransferase TRI3 Q9C1B7 TRI3_FUSSP Fusarium sporotrichioides 3 0.7111
Trichothecene 15-O-acetyltransferase TRI3 Q9C1B7 TRI3_FUSSP Fusarium sporotrichioides 3 0.7111
Polyprotein Q80J95 Q80J95_9CALI Murine norovirus 1 4 0.7102
Polyprotein Q80J95 Q80J95_9CALI Murine norovirus 1 4 0.7102
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 3 0.7097
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 3 0.7097
Angiotensin-converting enzyme Q10714 ACE_DROME Drosophila melanogaster 2 0.7085
Angiotensin-converting enzyme Q10714 ACE_DROME Drosophila melanogaster 2 0.7085
Gag-Pol polyprotein P04584 POL_HV2RO Human immunodeficiency virus type 2 subtype A 3 0.7069
Gag-Pol polyprotein P04584 POL_HV2RO Human immunodeficiency virus type 2 subtype A 3 0.7069
Mitochondrial poly(A) polymerase F1NBW0 F1NBW0_CHICK Gallus gallus 2 0.7060
Mitochondrial poly(A) polymerase F1NBW0 F1NBW0_CHICK Gallus gallus 2 0.7060
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7043
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7043
Dihydropteroate synthase Q81VW8 Q81VW8_BACAN Bacillus anthracis 3 0.7033
Dihydropteroate synthase Q81VW8 Q81VW8_BACAN Bacillus anthracis 3 0.7033
3-hydroxyanthranilate 3,4-dioxygenase Q1LCS4 3HAO_CUPMC Cupriavidus metallidurans 3 0.7021
3-hydroxyanthranilate 3,4-dioxygenase Q1LCS4 3HAO_CUPMC Cupriavidus metallidurans 3 0.7021
Cytidine and deoxycytidylate deaminase zinc-binding region Q82Y41 Q82Y41_NITEU Nitrosomonas europaea 3 0.7007
Cytidine and deoxycytidylate deaminase zinc-binding region Q82Y41 Q82Y41_NITEU Nitrosomonas europaea 3 0.7007

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