8-oxoerythraline - Compound Card

8-oxoerythraline

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8-oxoerythraline

Structure
Zoomed Structure
  • Family: Plantae - Leguminosae/Fabaceae
  • Kingdom: Plantae
  • Class: Alkaloid
Canonical Smiles CO[C@H]1C=CC2=CC(=O)N3[C@]2(C1)c1cc2OCOc2cc1CC3
InChI InChI=1S/C18H17NO4/c1-21-13-3-2-12-7-17(20)19-5-4-11-6-15-16(23-10-22-15)8-14(11)18(12,19)9-13/h2-3,6-8,13H,4-5,9-10H2,1H3/t13-,18-/m0/s1
InChIKey RNCIERMYMLFYAO-UGSOOPFHSA-N
Formula C18H17NO4
HBA 4
HBD 0
MW 311.34
Rotatable Bonds 1
TPSA 48.0
LogP 1.91
Number Rings 5
Number Aromatic Rings 1
Heavy Atom Count 23
Formal Charge 0
Fraction CSP3 0.39
Exact Mass 311.12
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Erythrina abyssinica Leguminosae/Fabaceae Plantae 1237573

Showing of synonyms

  • Mohammed MM, Ibrahim NA, et al. (2012). Anti-HIV-1 and cytotoxicity of the alkaloids of Erythrina abyssinica Lam. growing in Sudan. Natural Product Research,2012,26(17),1565-1575. [View] [PubMed]
Pubchem: 21599256
Chebi: 191061
Nmrshiftdb2: 70004442

No compound-protein relationship available.

Structure

SMILES: C1CC=CC(C123)=CC(=O)N3CCc4c2cc5c(c4)OCO5

Level: 0

Mol. Weight: 311.34 g/mol

Anti-hiv
Cytotoxicity

Absorption

Caco-2 (logPapp)
-4.73
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.210
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.33

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.760
Plasma Protein Binding
52.57
Steady State Volume of Distribution
-

Metabolism

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

Excretion

Clearance
7.720
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Toxic
Bioconcentration Factor
0.320
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
-0.060
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
5.480
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
-2.320
Rat (Acute)
2.490
Rat (Chronic Oral)
1.680
Fathead Minnow
4.160
Respiratory Disease
Safe
Skin Sensitisation
Toxic
SR-ARE
Toxic
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Safe

General Properties

Boiling Point
413.050
Hydration Free Energy
-8.440
Log(D) at pH=7.4
2.220
Log(P)
2.1
Log S
-3.05
Log(Vapor Pressure)
-7.42
Melting Point
190.3
pKa Acid
9.5
pKa Basic
5.76
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
NAD-capped RNA hydrolase NudC P32664 NUDC_ECOLI Escherichia coli 3 0.8723
NAD-capped RNA hydrolase NudC P32664 NUDC_ECOLI Escherichia coli 3 0.8723
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.8615
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.8615
cAMP-dependent protein kinase type I-alpha regulatory subunit P00514 KAP0_BOVIN Bos taurus 3 0.8564
cAMP-dependent protein kinase type I-alpha regulatory subunit P00514 KAP0_BOVIN Bos taurus 3 0.8564
Na(+):neurotransmitter symporter (Snf family) O67854 O67854_AQUAE Aquifex aeolicus 3 0.8326
Na(+):neurotransmitter symporter (Snf family) O67854 O67854_AQUAE Aquifex aeolicus 3 0.8326
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8315
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8315
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8286
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8286
Abscisic acid receptor PYR1 O49686 PYR1_ARATH Arabidopsis thaliana 3 0.8165
Abscisic acid receptor PYR1 O49686 PYR1_ARATH Arabidopsis thaliana 3 0.8165
Aromatase P11511 CP19A_HUMAN Homo sapiens 3 0.8053
Aromatase P11511 CP19A_HUMAN Homo sapiens 3 0.8053
Casein kinase II subunit alpha' P19784 CSK22_HUMAN Homo sapiens 3 0.8050
Metapyrocatechase Q7WYF5 Q7WYF5_9PSED Pseudomonas alkylphenolica 3 0.8050
Metapyrocatechase Q7WYF5 Q7WYF5_9PSED Pseudomonas alkylphenolica 3 0.8050
Casein kinase II subunit alpha' P19784 CSK22_HUMAN Homo sapiens 3 0.8050
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.8040
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.8040
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 3 0.8022
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 3 0.8022
Acetylcholinesterase P04058 ACES_TETCF Tetronarce californica 3 0.7832
Acetylcholinesterase P04058 ACES_TETCF Tetronarce californica 3 0.7832
Abscisic acid receptor PYL3 Q9SSM7 PYL3_ARATH Arabidopsis thaliana 3 0.7689
Abscisic acid receptor PYL3 Q9SSM7 PYL3_ARATH Arabidopsis thaliana 3 0.7689
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 3 0.7666
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 3 0.7666
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.7652
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.7652
Abscisic acid receptor PYL9 Q84MC7 PYL9_ARATH Arabidopsis thaliana 3 0.7628
Abscisic acid receptor PYL9 Q84MC7 PYL9_ARATH Arabidopsis thaliana 3 0.7628
Fatty acid-binding protein, liver P80226 FABPL_CHICK Gallus gallus 2 0.7545
Fatty acid-binding protein, liver P80226 FABPL_CHICK Gallus gallus 2 0.7545
Abscisic acid receptor PYR1 O49686 PYR1_ARATH Arabidopsis thaliana 3 0.7485
Abscisic acid receptor PYR1 O49686 PYR1_ARATH Arabidopsis thaliana 3 0.7485
Beta-2 adrenergic receptor P07550 ADRB2_HUMAN Homo sapiens 3 0.7443
Beta-2 adrenergic receptor P07550 ADRB2_HUMAN Homo sapiens 3 0.7443
11-beta-hydroxysteroid dehydrogenase 1 P28845 DHI1_HUMAN Homo sapiens 3 0.7354
11-beta-hydroxysteroid dehydrogenase 1 P28845 DHI1_HUMAN Homo sapiens 3 0.7354
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase Q05603 COBT_SALTY Salmonella typhimurium 2 0.7353
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase Q05603 COBT_SALTY Salmonella typhimurium 2 0.7353
Sex hormone-binding globulin P04278 SHBG_HUMAN Homo sapiens 3 0.7350
Sex hormone-binding globulin P04278 SHBG_HUMAN Homo sapiens 3 0.7350
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 2 0.7310
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 2 0.7310
Nuclear receptor ROR-gamma P51449 RORG_HUMAN Homo sapiens 2 0.7259
Nuclear receptor ROR-gamma P51449 RORG_HUMAN Homo sapiens 2 0.7259
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 3 0.7232
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 3 0.7232
Mitochondrial poly(A) polymerase F1NBW0 F1NBW0_CHICK Gallus gallus 2 0.7214
Mitochondrial poly(A) polymerase F1NBW0 F1NBW0_CHICK Gallus gallus 2 0.7214
Beta-galactoside-specific lectin 4 Q6ITZ3 ML4_VISAL Viscum album 2 0.7210
Beta-galactoside-specific lectin 4 Q6ITZ3 ML4_VISAL Viscum album 2 0.7210
Polymerase acidic protein C3W5S0 C3W5S0_I09A0 Influenza A virus 2 0.7187
Polymerase acidic protein C3W5S0 C3W5S0_I09A0 Influenza A virus 2 0.7187
Retinol dehydratase Q26490 Q26490_SPOFR Spodoptera frugiperda 3 0.7183
Retinol dehydratase Q26490 Q26490_SPOFR Spodoptera frugiperda 3 0.7183
Aldo-keto reductase family 1 member C1 Q04828 AK1C1_HUMAN Homo sapiens 2 0.7169
Aldo-keto reductase family 1 member C1 Q04828 AK1C1_HUMAN Homo sapiens 2 0.7169
17-beta-hydroxysteroid dehydrogenase 14 Q9BPX1 DHB14_HUMAN Homo sapiens 2 0.7103
17-beta-hydroxysteroid dehydrogenase 14 Q9BPX1 DHB14_HUMAN Homo sapiens 2 0.7103
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.7066
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.7066
Sex hormone-binding globulin P04278 SHBG_HUMAN Homo sapiens 3 0.7032
Sex hormone-binding globulin P04278 SHBG_HUMAN Homo sapiens 3 0.7032
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.7026
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.7026
ADP compounds hydrolase NudE P45799 NUDE_ECOLI Escherichia coli 2 0.7011
ADP compounds hydrolase NudE P45799 NUDE_ECOLI Escherichia coli 2 0.7011

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