1,2,4-trihydroxynaphthalene-2-O-beta-D-glucopyranoside - Compound Card

1,2,4-trihydroxynaphthalene-2-O-beta-D-glucopyranoside

Select a section from the left sidebar

1,2,4-trihydroxynaphthalene-2-O-beta-D-glucopyranoside

Structure
Zoomed Structure
  • Family: Plantae - Lythraceae
  • Kingdom: Plantae
  • Class: Phenolic
    • Subclass: Phenolic Glycoside
Canonical Smiles OCC1O[C@@H](Oc2cc(O)c3c(c2O)cccc3)[C@H](C([C@@H]1O)O)O
InChI InChI=1S/C16H18O8/c17-6-11-13(20)14(21)15(22)16(24-11)23-10-5-9(18)7-3-1-2-4-8(7)12(10)19/h1-5,11,13-22H,6H2/t11?,13-,14?,15+,16-/m1/s1
InChIKey LZEDTBAXTHUPTF-YHMKUFFLSA-N
Formula C16H18O8
HBA 8
HBD 6
MW 338.31
Rotatable Bonds 3
TPSA 139.84
LogP -0.57
Number Rings 3
Number Aromatic Rings 2
Heavy Atom Count 24
Formal Charge 0
Fraction CSP3 0.38
Exact Mass 338.1
Number of Lipinski Rule Violations 1
# Species Family Kingdom NCBI Taxonomy ID
1 Lawsonia inermis Lythraceae Plantae 141191

Showing of synonyms

  • Dhouafli Z, Ben Jannet H, et al. (2019). 1,2,4-trihydroxynaphthalene-2-O-β-D-glucopyranoside: A new powerful antioxidant and inhibitor of Aβ42 aggregation isolated from the leaves of Lawsonia inermis. Natural product research, 2019, 33(10), 1406-1414. [View] [PubMed]

No compound-protein relationship available.

Structure

SMILES: c1cccc(c12)ccc(c2)OC3CCCCO3

Level: 1

Mol. Weight: 338.31 g/mol

Structure

SMILES: c1cccc(c12)cccc2

Level: 0

Mol. Weight: 338.31 g/mol

Structure

SMILES: C1CCOCC1

Level: 0

Mol. Weight: 338.31 g/mol

Antioxidant

Absorption

Caco-2 (logPapp)
-6.11
Human Oral Bioavailability 20%
Non-Bioavailable
Human Intestinal Absorption
Non-Absorbed
Madin-Darby Canine Kidney
-5.11
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-0.81

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
0.87
Plasma Protein Binding
67.82
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
13.64
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-0.86
Biodegradation
Toxic
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
1.03
Liver Injury II
Safe
hERG Blockers
Safe
Daphnia Maga
5.34
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
-1.45
Rat (Acute)
2.2
Rat (Chronic Oral)
3.96
Fathead Minnow
3.88
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
476.31
Hydration Free Energy
-14.04
Log(D) at pH=7.4
0.37
Log(P)
-0.39
Log S
-2.78
Log(Vapor Pressure)
-10.59
Melting Point
192.74
pKa Acid
5.01
pKa Basic
5.12
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.9374
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 3 0.9339
4-diphosphocytidyl-2-C-methyl-D-erythritol kinase O67060 ISPE_AQUAE Aquifex aeolicus 3 0.9005
Serpin domain-containing protein H0ZQY2 H0ZQY2_TAEGU Taeniopygia guttata 3 0.8965
Neocarzinostatin P0A3R9 NCZS_STRCZ Streptomyces carzinostaticus 3 0.8954
Flavin-dependent monooxygenase Q93L51 TETX_BACT4 Bacteroides thetaiotaomicron 3 0.8818
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase Q9TQS6 DHDH_MACFA Macaca fascicularis 3 0.8677
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.8602
Thiamine-phosphate synthase P39594 THIE_BACSU Bacillus subtilis 3 0.8381
Cathepsin S P25774 CATS_HUMAN Homo sapiens 3 0.8331
Isoleucine--tRNA ligase P56690 SYI_THET8 Thermus thermophilus 3 0.8304
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.8154
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.8038
Polyprotein Q80J95 Q80J95_9CALI Murine norovirus 1 3 0.7857
Purine nucleoside phosphorylase P00491 PNPH_HUMAN Homo sapiens 3 0.7764
Tetracycline repressor protein class B from transposon Tn10 P04483 TETR2_ECOLX Escherichia coli 3 0.7758
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 4 0.7751
Polyribonucleotide nucleotidyltransferase A7ZS61 PNP_ECO24 Escherichia coli O139:H28 3 0.7749
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7736
Nuclear receptor subfamily 4immunitygroup A member 1 P22736 NR4A1_HUMAN Homo sapiens 3 0.7722
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7528
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7473
Nitric oxide synthase oxygenase O34453 NOSO_BACSU Bacillus subtilis 4 0.7461
Albumin P02768 ALBU_HUMAN Homo sapiens 3 0.7461
Poly [ADP-ribose] polymerase 1 P26446 PARP1_CHICK Gallus gallus 3 0.7335
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 3 0.7332
Type II methyltransferase M.TaqI P14385 MTTA_THEAQ Thermus aquaticus 3 0.7183
L-lactate dehydrogenase A chain P04642 LDHA_RAT Rattus norvegicus 3 0.7159
Tryptophan synthase alpha chain P00929 TRPA_SALTY Salmonella typhimurium 2 0.7121
Oxygenase Q194P4 Q194P4_STRAA Streptomyces argillaceus 3 0.7103
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7099
NAD-capped RNA hydrolase NudC P32664 NUDC_ECOLI Escherichia coli 3 0.7097
Ras-related protein Ral-B P11234 RALB_HUMAN Homo sapiens 3 0.7068
RNA-dependent RNA polymerase Q6A562 Q6A562_9VIRU Thosea asigna virus 3 0.7049
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7048
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.7043
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 3 0.7008
Sensor histidine kinase EnvZ P0AEJ4 ENVZ_ECOLI Escherichia coli 3 0.7001

Download SDF