2-hydroxynoracronycine - Compound Card

2-hydroxynoracronycine

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2-hydroxynoracronycine

Structure
Zoomed Structure
  • Family: Plantae - Rutaceae
  • Kingdom: Plantae
  • Class: Alkaloid
    • Subclass: Acridone Alkaloid
Canonical Smiles Oc1c2OC(C)(C)C=Cc2c2c(c1O)c(=O)c1c(n2C)cccc1
InChI InChI=1S/C19H17NO4/c1-19(2)9-8-11-14-13(16(22)17(23)18(11)24-19)15(21)10-6-4-5-7-12(10)20(14)3/h4-9,22-23H,1-3H3
InChIKey AVMGCYSIBIQWGG-UHFFFAOYSA-N
Formula C19H17NO4
HBA 5
HBD 2
MW 323.35
Rotatable Bonds 0
TPSA 71.69
LogP 3.29
Number Rings 4
Number Aromatic Rings 3
Heavy Atom Count 24
Formal Charge 0
Fraction CSP3 0.21
Exact Mass 323.12
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Citrus × paradisi Rutaceae Plantae 37656

Showing of synonyms

  • Essombe Malolo FA, Bellier Tabekoueng G, et al. (2022). Chemical Constituents of the Stem Bark of the Hybrid Plant Citrus × paradisi Macfad. (Rutaceae).. Chemistry & biodiversity,2022, 19(7), e202101033. [View] [PubMed]
Pubchem: 5491992

No compound-protein relationship available.

Structure

SMILES: C1=CCOc(cc2)c1c(c23)[nH]c4c(c3=O)cccc4

Level: 0

Mol. Weight: 323.35 g/mol

Cytotoxic

Absorption

Caco-2 (logPapp)
-4.74
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.680
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-1.28

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
1.110
Plasma Protein Binding
60.97
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
Non-Inhibitor
CYP 2C9 Substrate
Substrate
CYP 2D6 Inhibitor
Inhibitor
CYP 2D6 Substrate
Non-Substrate
CYP 3A4 Inhibitor
Non-Inhibitor
CYP 3A4 Substrate
Non-Substrate
OATP1B1
Non-Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
3.560
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Toxic
Bioconcentration Factor
1.030
Biodegradation
Safe
Carcinogenesis
Toxic
Crustacean
Toxic
Liver Injury I (DILI)
Toxic
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.640
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
4.320
Micronucleos
Toxic
NR-AhR
Toxic
NR-AR
Safe
NR-AR-LBD
Safe
NR-Aromatase
Safe
NR-ER
Safe
NR-ER-LBD
Safe
NR-GR
Toxic
NR-PPAR-gamma
Safe
NR-TR
Safe
T. Pyriformis
3.530
Rat (Acute)
2.530
Rat (Chronic Oral)
2.430
Fathead Minnow
4.820
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
463.640
Hydration Free Energy
-11.700
Log(D) at pH=7.4
2.220
Log(P)
3.1
Log S
-4.63
Log(Vapor Pressure)
-9.12
Melting Point
240.58
pKa Acid
5.14
pKa Basic
6.96
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Alpha-ketoglutarate-dependent dioxygenase FTO Q9C0B1 FTO_HUMAN Homo sapiens 3 0.8972
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.8925
Riboflavin biosynthesis protein Q9WZW1 Q9WZW1_THEMA Thermotoga maritima 4 0.8284
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.8255
Protein S100-A13 Q99584 S10AD_HUMAN Homo sapiens 3 0.7941
Capsid protein Q9WBP8 Q9WBP8_9VIRU Adeno-associated virus - 1 3 0.7924
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.7855
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7700
ATP-dependent molecular chaperone HSP82 P02829 HSP82_YEAST Saccharomyces cerevisiae 3 0.7596
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7589
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.7555
Activin receptor type-1 Q04771 ACVR1_HUMAN Homo sapiens 3 0.7525
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 4 0.7510
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7508
Tyrosine-protein kinase Lck P06239 LCK_HUMAN Homo sapiens 3 0.7465
Aurora kinase B-A Q6DE08 AUKBA_XENLA Xenopus laevis 3 0.7440
Phosphodiesterase Q53I60 Q53I60_TRYCR Trypanosoma cruzi 4 0.7418
Diphtheria toxin P00588 DTX_CORBE Corynephage beta 3 0.7399
Nuclear receptor subfamily 1 group I member 2 O75469 NR1I2_HUMAN Homo sapiens 3 0.7295
Sulfide-quinone reductase B7JBP8 SQRD_ACIF2 Acidithiobacillus ferrooxidans) 4 0.7284
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.7284
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7279
Dipeptidyl peptidase 4 P27487 DPP4_HUMAN Homo sapiens 3 0.7260
Lethal(3)malignant brain tumor-like protein 1 Q9Y468 LMBL1_HUMAN Homo sapiens 3 0.7259
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 4 0.7156
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 3 0.7140
Streptogramin A acetyltransferase P50870 VATD_ENTFC Enterococcus faecium 3 0.7112
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7109
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7080
Glutamate racemase Q9ZLT0 MURI_HELPJ Helicobacter pylori 3 0.7073
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7027
cGMP-dependent protein kinase, putative A5K0N4 A5K0N4_PLAVS Plasmodium vivax 3 0.7023
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7018

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