Auriculatin - Compound Card

Auriculatin

Select a section from the left sidebar

Auriculatin

Structure
Zoomed Structure
  • Family: Plantae - Leguminosae/Fabaceae
  • Kingdom: Plantae
  • Class: Flavonoid
    • Subclass: Isoflavonoid
Canonical Smiles CC(=CCc1c2OC(C)(C)C=Cc2c(c2c1occ(c2=O)c1ccc(cc1O)O)O)C
InChI InChI=1S/C25H24O6/c1-13(2)5-7-17-23-16(9-10-25(3,4)31-23)21(28)20-22(29)18(12-30-24(17)20)15-8-6-14(26)11-19(15)27/h5-6,8-12,26-28H,7H2,1-4H3
InChIKey IEKQCBVQJGWJRO-UHFFFAOYSA-N
Formula C25H24O6
HBA 6
HBD 3
MW 420.46
Rotatable Bonds 3
TPSA 100.13
LogP 5.27
Number Rings 4
Number Aromatic Rings 3
Heavy Atom Count 31
Formal Charge 0
Fraction CSP3 0.24
Exact Mass 420.16
Number of Lipinski Rule Violations 1
# Species Family Kingdom NCBI Taxonomy ID
1 Erythrina senegalensis Leguminosae/Fabaceae Plantae 157649
2 Erythrina senegalensis Leguminosae/Fabaceae Plantae 157649

Showing of synonyms

  • Oh WK, Lee C, et al. (2009). Diacylglycerol acyltransferase-inhibitory compounds from Erythrina senegalensis.. Archives of pharmacal research,2009, 32(1), 43-47. [View] [PubMed]
  • Lee J, Oh WK, et al. (2009). Prenylisoflavonoids from Erythrina senegalensis as novel HIV-1 protease inhibitors.. Planta medica,2009, 75(3), 268-270. [View] [PubMed]
Pubchem: 5358847
Chebi: 178567
Nmrshiftdb2: 60046408

No compound-protein relationship available.

Structure

SMILES: O1CC=Cc(c2)c1cc(c23)occ(c3=O)-c4ccccc4

Level: 1

Mol. Weight: 420.46 g/mol

Structure

SMILES: O=c1ccoc(c12)cc3c(c2)C=CCO3

Level: 0

Mol. Weight: 420.46 g/mol

Structure

SMILES: c1ccccc1

Level: 0

Mol. Weight: 420.46 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-5.04
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.86
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-0.4

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
1.31
Plasma Protein Binding
79.86
Steady State Volume of Distribution
-

Metabolism

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

Excretion

Clearance
3.74
Organic Cation Transporter 2
Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
1.47
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Toxic
Eye Corrosion
Safe
Eye Irritation
Toxic
Maximum Tolerated Dose
1.02
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
6.01
Micronucleos
Toxic
NR-AhR
Toxic
NR-AR
Safe
NR-AR-LBD
Safe
NR-Aromatase
Toxic
NR-ER
Toxic
NR-ER-LBD
Safe
NR-GR
Toxic
NR-PPAR-gamma
Safe
NR-TR
Toxic
T. Pyriformis
-31.95
Rat (Acute)
2.52
Rat (Chronic Oral)
2.53
Fathead Minnow
5.31
Respiratory Disease
Toxic
Skin Sensitisation
Toxic
SR-ARE
Toxic
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Toxic
SR-p53
Safe

General Properties

Boiling Point
518.68
Hydration Free Energy
-5.23
Log(D) at pH=7.4
4.55
Log(P)
5.68
Log S
-6.69
Log(Vapor Pressure)
-9.86
Melting Point
230.37
pKa Acid
7.85
pKa Basic
7.03
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Histone deacetylase 4 P56524 HDAC4_HUMAN Homo sapiens 3 0.9424
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.9116
IOMT 3 Q06YR3 Q06YR3_MEDTR Medicago truncatula 4 0.9066
Lactoperoxidase A0A452E9Y6 PERL_CAPHI Capra hircus 3 0.8905
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 5 0.8898
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.8766
L-lactate dehydrogenase A chain P04642 LDHA_RAT Rattus norvegicus 3 0.8744
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 3 0.8727
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.8372
Serine/threonine-protein kinase 24 Q9Y6E0 STK24_HUMAN Homo sapiens 3 0.8346
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.8153
Mitogen-activated protein kinase 8 P45983 MK08_HUMAN Homo sapiens 3 0.8124
TetR family transcriptional regulator Q58L87 Q58L87_MYCSM Mycolicibacterium smegmatis 3 0.8059
Proton-gated ion channel Q7NDN8 GLIC_GLOVI Gloeobacter violaceus 3 0.8028
Dipeptidyl peptidase 4 P27487 DPP4_HUMAN Homo sapiens 3 0.8027
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.8020
ATP-dependent molecular chaperone HSP82 P02829 HSP82_YEAST Saccharomyces cerevisiae 3 0.7984
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7890
Tyrosine-protein kinase SYK P43405 KSYK_HUMAN Homo sapiens 3 0.7872
Beta-2-microglobulin P61769 B2MG_HUMAN Homo sapiens 3 0.7868
Endothiapepsin P11838 CARP_CRYPA Cryphonectria parasitica 3 0.7839
Lethal(3)malignant brain tumor-like protein 1 Q9Y468 LMBL1_HUMAN Homo sapiens 3 0.7802
Peptidyl-prolyl cis-trans isomerase FKBP5 Q13451 FKBP5_HUMAN Homo sapiens 3 0.7794
Genome polyprotein O92972 POLG_HCVJ4 Hepatitis C virus genotype 1b 3 0.7772
Integrin alpha-L P20701 ITAL_HUMAN Homo sapiens 3 0.7764
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 3 0.7740
Acetolactate synthase, chloroplastic P17597 ILVB_ARATH Arabidopsis thaliana 3 0.7727
Capsid protein Q9WBP8 Q9WBP8_9VIRU Adeno-associated virus - 1 3 0.7703
Serine/threonine-protein kinase 10 O94804 STK10_HUMAN Homo sapiens 3 0.7694
F420-dependent NADP reductase O29370 FNO_ARCFU Archaeoglobus fulgidus 4 0.7681
Genome polyprotein O92972 POLG_HCVJ4 Hepatitis C virus genotype 1b 3 0.7568
Cis-2,3-dihydrobiphenyl-2,3-diol dehydrogenase Q46381 BPHB_COMTE Comamonas testosteroni 3 0.7559
Genome polyprotein O92972 POLG_HCVJ4 Hepatitis C virus genotype 1b 3 0.7551
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7540
Lactoperoxidase P80025 PERL_BOVIN Bos taurus 3 0.7537
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7513
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform P48736 PK3CG_HUMAN Homo sapiens 4 0.7512
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7458
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.7454
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.7445
Fatty acid-binding protein, liver P80226 FABPL_CHICK Gallus gallus 3 0.7429
Genome polyprotein P26663 POLG_HCVBK Hepatitis C virus genotype 1b 3 0.7379
Bromodomain adjacent to zinc finger domain protein 2B Q9UIF8 BAZ2B_HUMAN Homo sapiens 3 0.7345
Apoptosis regulator Bcl-2 P10415 BCL2_HUMAN Homo sapiens 3 0.7305
Cytosolic purine 5'-nucleotidase P49902 5NTC_HUMAN Homo sapiens 2 0.7230
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7185
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.7181
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7167
Nucleoside diphosphate kinase P15266 NDK_MYXXA Myxococcus xanthus 3 0.7157
Lysozyme C II P11941 LYSC2_ONCMY Oncorhynchus mykiss 3 0.7155
S-adenosylmethionine decarboxylase proenzyme P17707 DCAM_HUMAN Homo sapiens 3 0.7132
Pancreatic alpha-amylase P04746 AMYP_HUMAN Homo sapiens 3 0.7101
Thymidylate synthase P00469 TYSY_LACCA Lacticaseibacillus casei 3 0.7096
Glucose-1-phosphate thymidylyltransferase Q9HU22 Q9HU22_PSEAE Pseudomonas aeruginosa 3 0.7093
Tyrosine-protein kinase Lck P06239 LCK_HUMAN Homo sapiens 3 0.7088
Virulence sensor histidine kinase PhoQ P0DM80 PHOQ_SALTY Salmonella typhimurium 3 0.7051
Protein S100-A13 Q99584 S10AD_HUMAN Homo sapiens 3 0.7007

Download SDF