(Z)-lespedezic acid - Compound Card

(Z)-lespedezic acid

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(Z)-lespedezic acid

Structure
Zoomed Structure
  • Family: Plantae - Gunneraceae
  • Kingdom: Plantae
  • Class: Phenolic
    • Subclass: Phenolic Glucoside
Canonical Smiles OC[C@H]1O[C@@H](O/C(=C\c2ccc(cc2)O)/C(=O)O)[C@@H]([C@H]([C@@H]1O)O)O
InChI InChI=1S/C15H18O9/c16-6-10-11(18)12(19)13(20)15(24-10)23-9(14(21)22)5-7-1-3-8(17)4-2-7/h1-5,10-13,15-20H,6H2,(H,21,22)/b9-5-/t10-,11-,12+,13-,15-/m1/s1
InChIKey PLVRRSCUONTHAT-KXKMCBQKSA-N
Formula C15H18O9
HBA 8
HBD 6
MW 342.3
Rotatable Bonds 5
TPSA 156.91
LogP -1.37
Number Rings 2
Number Aromatic Rings 1
Heavy Atom Count 24
Formal Charge 0
Fraction CSP3 0.4
Exact Mass 342.1
Number of Lipinski Rule Violations 1
# Species Family Kingdom NCBI Taxonomy ID
1 Gunnera perpensa Gunneraceae Plantae 138603

Showing of synonyms

  • Khan F, Peter XK, et al. (2004). Venusol from Gunnera perpensa: structural and activity studies. Phytochemistry, 2004, 65(8), 1117–1121. [View]
Pubchem: 11291931

No compound-protein relationship available.

Structure

SMILES: c1ccccc1C=COC2CCCCO2

Level: 1

Mol. Weight: 342.3 g/mol

Structure

SMILES: C1CCOCC1

Level: 0

Mol. Weight: 342.3 g/mol

Structure

SMILES: c1ccccc1

Level: 0

Mol. Weight: 342.3 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-5.94
Human Oral Bioavailability 20%
Non-Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-5.220
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-1.18

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
0.630
Plasma Protein Binding
56.9
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
5.190
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-2.210
Biodegradation
Toxic
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.840
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
4.100
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
-2.480
Rat (Acute)
1.910
Rat (Chronic Oral)
3.530
Fathead Minnow
4.070
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
494.270
Hydration Free Energy
-17.340
Log(D) at pH=7.4
-2.550
Log(P)
-0.91
Log S
-1.37
Log(Vapor Pressure)
-12.1
Melting Point
157.76
pKa Acid
2.76
pKa Basic
6.16
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Endothiapepsin P11838 CARP_CRYPA Cryphonectria parasitica 3 0.8933
Ras-related protein Ral-B P11234 RALB_HUMAN Homo sapiens 3 0.8790
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.8590
D-aminoacyl-tRNA deacylase Q8IIS0 DTD_PLAF7 Plasmodium falciparum 3 0.8514
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.8453
ATP-dependent molecular chaperone HSP82 P02829 HSP82_YEAST Saccharomyces cerevisiae 3 0.8380
NADPH-dependent oxidoreductase 2-alkenal reductase Q39172 AER_ARATH Arabidopsis thaliana 3 0.8226
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase Q9TQS6 DHDH_MACFA Macaca fascicularis 3 0.8111
N-acetyltransferase domain-containing protein Q9HV14 Q9HV14_PSEAE Pseudomonas aeruginosa 3 0.8060
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7785
Dihydrofolate reductase P00378 DYR_CHICK Gallus gallus 3 0.7744
Ficolin-2 Q15485 FCN2_HUMAN Homo sapiens 3 0.7725
Tyrosine-protein kinase JAK3 P52333 JAK3_HUMAN Homo sapiens 3 0.7678
Polymerase acidic protein C3W5S0 C3W5S0_I09A0 Influenza A virus 3 0.7669
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7635
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase Q05603 COBT_SALTY Salmonella typhimurium 2 0.7508
3-hydroxyanthranilate 3,4-dioxygenase Q1LCS4 3HAO_CUPMC Cupriavidus metallidurans 2 0.7364
2',3'-cyclic-nucleotide 3'-phosphodiesterase P16330 CN37_MOUSE Mus musculus 3 0.7349
Cytidine and deoxycytidylate deaminase zinc-binding region Q82Y41 Q82Y41_NITEU Nitrosomonas europaea 4 0.7285
5'-methylthioadenosine/S-adenosylhomocysteine nucleosidase Q81LL4 MTNN_BACAN Bacillus anthracis 2 0.7256
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7214
5-formyltetrahydrofolate cyclo-ligase P75430 MTHFS_MYCPN Mycoplasma pneumoniae 2 0.7192
Phosphatidylinositol 5-phosphate 4-kinase type-2 beta P78356 PI42B_HUMAN Homo sapiens 3 0.7180
Purine nucleoside phosphorylase DeoD-type O34925 DEOD_BACSU Bacillus subtilis 3 0.7172
Mitochondrial poly(A) polymerase F1NBW0 F1NBW0_CHICK Gallus gallus 2 0.7124
Cyclin-dependent kinase 9 P50750 CDK9_HUMAN Homo sapiens 3 0.7095
Bifunctional epoxide hydrolase 2 P34913 HYES_HUMAN Homo sapiens 2 0.7084
4-diphosphocytidyl-2-C-methyl-D-erythritol kinase B1MKD5 B1MKD5_MYCA9 Mycobacteroides abscessus 3 0.7082
5-methyltetrahydropteroyltriglutamate--homocysteine methyltransferase 1 O50008 METE1_ARATH Arabidopsis thaliana 2 0.7072
Purine nucleoside phosphorylase DeoD-type B1JL34 DEOD_YERPY Yersinia pseudotuberculosis serotype O:3 2 0.7041
Acetolactate synthase, chloroplastic P17597 ILVB_ARATH Arabidopsis thaliana 2 0.7028

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