Eleutherolic acid - Compound Card

Eleutherolic acid

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Eleutherolic acid

Structure
Zoomed Structure
  • Family: Plantae - Ancistrocladaceae
  • Kingdom: Plantae
  • Class: Naphthalene Derivative
Canonical Smiles OC(=O)c1cc(O)c2c(c1)cccc2C
InChI InChI=1S/C12H10O3/c1-7-3-2-4-8-5-9(12(14)15)6-10(13)11(7)8/h2-6,13H,1H3,(H,14,15)
InChIKey ULBVJZQHBHJPNL-UHFFFAOYSA-N
Formula C12H10O3
HBA 2
HBD 2
MW 202.21
Rotatable Bonds 1
TPSA 57.53
LogP 2.55
Number Rings 2
Number Aromatic Rings 2
Heavy Atom Count 15
Formal Charge 0
Fraction CSP3 0.08
Exact Mass 202.06
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Ancistrocladus ealaensis Ancistrocladaceae Plantae 714098

Showing of synonyms

  • Bringmann G, Hamm A, et al. (2000). Ancistroealaines A and B, two new bioactive naphthylisoquinolines, and related naphthoic acids from Ancistrocladus ealaensis. Journal of natural products,2000, 63(11), 1465-1470. [View] [PubMed]
Pubchem: 73013816
Nmrshiftdb2: 70048438

No compound-protein relationship available.

Structure

SMILES: c1cccc(c12)cccc2

Level: 0

Mol. Weight: 202.21 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.6
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.6
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.04

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.99
Plasma Protein Binding
65.47
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
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
9.7
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Safe
Bioconcentration Factor
0.41
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Toxic
Eye Corrosion
Safe
Eye Irritation
Toxic
Maximum Tolerated Dose
1.45
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
3.03
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
1.56
Rat (Acute)
2.32
Rat (Chronic Oral)
2.96
Fathead Minnow
3.78
Respiratory Disease
Toxic
Skin Sensitisation
Safe
SR-ARE
Safe
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Safe

General Properties

Boiling Point
331.08
Hydration Free Energy
-9.48
Log(D) at pH=7.4
0.72
Log(P)
3.03
Log S
-3.4
Log(Vapor Pressure)
-5.97
Melting Point
217.95
pKa Acid
5.11
pKa Basic
2.49
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 3 0.9661
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.9379
NADPH dehydrogenase 1 Q02899 OYE1_SACPS Saccharomyces pastorianus 3 0.8886
Glutathione S-transferase P P09211 GSTP1_HUMAN Homo sapiens 3 0.8820
4-chlorobenzoyl CoA ligase Q8GN86 Q8GN86_9BURK Alcaligenes sp. AL3007 3 0.8601
Gag-Pol polyprotein P03366 POL_HV1B1 Human immunodeficiency virus type 1 group M subtype B 3 0.8571
Sulfotransferase 2A1 Q06520 ST2A1_HUMAN Homo sapiens 3 0.8560
Sulfotransferase 2A1 Q06520 ST2A1_HUMAN Homo sapiens 3 0.8519
4-chlorobenzoyl CoA ligase Q8GN86 Q8GN86_9BURK Alcaligenes sp. AL3007 3 0.8334
Protocatechuate 3,4-dioxygenase beta chain P00437 PCXB_PSEPU Pseudomonas putida 3 0.8319
Cytochrome P450 monooxygenase Q5YNS8 Q5YNS8_NOCFA Nocardia farcinica 3 0.8247
Glutathione S-transferase A1 P08263 GSTA1_HUMAN Homo sapiens 3 0.8234
Succinate dehydrogenase flavoprotein subunit P0AC41 SDHA_ECOLI Escherichia coli 3 0.8227
Gag-Pol polyprotein P03366 POL_HV1B1 Human immunodeficiency virus type 1 group M subtype B 3 0.8186
Protocatechuate 3,4-dioxygenase beta chain P00437 PCXB_PSEPU Pseudomonas putida 3 0.8117
Albumin P02768 ALBU_HUMAN Homo sapiens 3 0.8048
2,7-dihydroxy-5-methyl-1-naphthoate 7-O-methyltransferase Q84HC8 NCSB1_STRCZ Streptomyces carzinostaticus 3 0.8008
Dihydroorotate dehydrogenase (quinone), mitochondrial Q08210 PYRD_PLAF7 Plasmodium falciparum 3 0.7988
Probable esterase KAI2 Q9SZU7 KAI2_ARATH Arabidopsis thaliana 3 0.7973
Biflaviolin synthase CYP158A1 Q9KZF5 C1581_STRCO Streptomyces coelicolor / M145) 3 0.7872
ADP-ribosylation factor 1 P84080 ARF1_BOVIN Bos taurus 3 0.7794
Bromodomain adjacent to zinc finger domain protein 2B Q9UIF8 BAZ2B_HUMAN Homo sapiens 2 0.7786
Aldo-keto reductase family 1 member A1 P50578 AK1A1_PIG Sus scrofa 3 0.7687
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 3 0.7670
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7668
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase Q9TQS6 DHDH_MACFA Macaca fascicularis 3 0.7658
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7657
ADP-ribosylation factor 1 P84080 ARF1_BOVIN Bos taurus 3 0.7561
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7543
11-beta-hydroxysteroid dehydrogenase 1 P50172 DHI1_MOUSE Mus musculus 2 0.7516
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.7508
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7488
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.7466
Aldo-keto reductase family 1 member C3 P42330 AK1C3_HUMAN Homo sapiens 3 0.7451
Nuclear receptor subfamily 1 group I member 3 O35627 NR1I3_MOUSE Mus musculus 2 0.7435
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 3 0.7432
Cytochrome P450 monooxygenase Q5YNS8 Q5YNS8_NOCFA Nocardia farcinica 3 0.7417
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7411
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7404
Cytochrome P450 monooxygenase Q5YNS8 Q5YNS8_NOCFA Nocardia farcinica 3 0.7375
Albumin P02768 ALBU_HUMAN Homo sapiens 3 0.7371
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7358
2,7-dihydroxy-5-methyl-1-naphthoate 7-O-methyltransferase Q84HC8 NCSB1_STRCZ Streptomyces carzinostaticus 3 0.7353
Polymerase acidic protein Q5EP34 Q5EP34_9INFA Influenza A virus 3 0.7341
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 2 0.7306
Corticosteroid-binding globulin P08185 CBG_HUMAN Homo sapiens 3 0.7254
Pheromone-binding protein ASP1 Q9U9J6 Q9U9J6_APIME Apis mellifera 2 0.7248
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 2 0.7245
Fatty acid-binding protein, liver P80226 FABPL_CHICK Gallus gallus 2 0.7242
Aldo-keto reductase family 1 member B1 P15121 ALDR_HUMAN Homo sapiens 4 0.7239
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 2 0.7236
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.7234
Nitroreductase domain-containing protein Q8DW21 Q8DW21_STRMU Streptococcus mutans serotype c 3 0.7228
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.7218
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.7183
Prostaglandin reductase 2 Q8N8N7 PTGR2_HUMAN Homo sapiens 2 0.7154
Sex hormone-binding globulin P04278 SHBG_HUMAN Homo sapiens 2 0.7144
4-diphosphocytidyl-2-C-methyl-D-erythritol kinase O67060 ISPE_AQUAE Aquifex aeolicus 3 0.7119
Bromodomain-containing protein 2 P25440 BRD2_HUMAN Homo sapiens 3 0.7104
Jasmonoyl--L-amino acid synthetase JAR1 Q9SKE2 JAR1_ARATH Arabidopsis thaliana 3 0.7079
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.7050
17-beta-hydroxysteroid dehydrogenase type 1 P14061 DHB1_HUMAN Homo sapiens 2 0.7038
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7021
Glutamate receptor 3 P19492 GRIA3_RAT Rattus norvegicus 3 0.7010
Aromatase P11511 CP19A_HUMAN Homo sapiens 3 0.7007
NADPH-dependent oxidoreductase 2-alkenal reductase Q39172 AER_ARATH Arabidopsis thaliana 2 0.7004

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