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5-hydroxynoracronycine
- Family: Plantae - Rutaceae
- Kingdom: Plantae
-
Class: Alkaloid
- Subclass: Acridone Alkaloid
| Canonical Smiles | Oc1cc2OC(C)(C)C=Cc2c2c1c(=O)c1c(n2C)c(O)ccc1 |
|---|---|
| InChI | InChI=1S/C19H17NO4/c1-19(2)8-7-10-14(24-19)9-13(22)15-17(10)20(3)16-11(18(15)23)5-4-6-12(16)21/h4-9,21-22H,1-3H3 |
| InChIKey | JZQDCDLYNFZBIG-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 aurantium | Rutaceae | Plantae | 43166 |
| 2 | Citrus clementina | Rutaceae | Plantae | 85681 |
| 3 | Citrus reticulata | Rutaceae | Plantae | 85571 |
Showing of synonyms
5-hydroxynoracronycine
11-Hydroxynoracronycine
Alkaloid A from Atalantia ceylanica
54E45U4Q3N
Alkaloid A, from Atalantia ceylanica
NSC 162687
NSC-162687
5-HYDROXYNORACRONYCIN
UNII-54E45U4Q3N
DTXSID50181535
3,12-Dihydro-6,11-dihydroxy-3,312-trimethyl-7H-pyrano(2,3-c)acridin-7-one
3,12-DIHYDRO-6,11-DIHYDROXY-3,3,12-TRIMETHYL-7H-PYRANO(2,3-C)ACRIDIN-7-ONE
DTXCID90104026
7H-Pyrano(2,3-c)acridin-7-one, 3,12-dihydro-6,11-dihydroxy-3,3,12-trimethyl-(8CI)
7H-Pyrano(2,3-c)acridin-7-one, 3,12-dihydro-6,11-dihydroxy-3,3,12-trimethyl-(8CI)(9CI)
Jzqdcdlynfzbig-uhfffaoysa-n
27067-70-5
11-Hydroxy-O-demethylacronine
CHEMBL447169
CHEBI:69044
7H-Pyrano[2,3-c]acridin-7-one, 3,12-dihydro-6,11-dihydroxy-3,3,12-trimethyl-
7H-Pyrano(2,3-c)acridin-7-one, 3,12-dihydro-6,11-dihydroxy-3,3,12-trimethyl-
5-Hydroxyacronine
BDBM50336483
NSC162687
Q27137385
6,11-dihydroxy-3,3,12-trimethyl-pyrano[2,3-c]acridin-7-one
7H-Pyrano[2, 3,12-dihydro-6,11-dihydroxy-3,3,12-trimethyl-
6,11-Dihydroxy-3,3,12-trimethyl-3,12-dihydro-7H-pyrano[2,3-c]acridin-7-one #
- Bissim S, Kenmogne S, et al. (2019). Bioactive acridone alkaloids and their derivatives from Citrus aurantium (Rutaceae). Phytochemistry Letters, 2019, 29, 148-153. [View]
- Fomani M, Ngeufa Happi E, et al. (2016). Oxidative burst inhibition, cytotoxicity and antibacterial acriquinoline alkaloids from Citrus reticulate (Blanco).. Bioorganic & medicinal chemistry letters,2016, 26(2), 306-309. [View] [PubMed]
- Bissim S, Kenmogne S, et al. (2021). The chemistry and biological activities of Citrus clementina Hort. Ex Tanaka (Rutaceae), a vegetatively propagated species.. Natural product research,2021, 35(22), 4839-4842. [View] [PubMed]
Pubchem:
5378702
Cas:
27067-70-5
Chebi:
69044
Nmrshiftdb2:
70003119
Metabolights:
MTBLC69044
Chembl:
CHEMBL447169
Comptox:
DTXSID50181535
Bindingdb:
50336483
No compound-protein relationship available.
SMILES: C1=CCOc(cc2)c1c(c23)[nH]c4c(c3=O)cccc4
Level: 0
Mol. Weight: 323.35 g/mol
Anti-diabetic
Anti-inflammatory
Antioxidant
Absorption
- Caco-2 (logPapp)
- -4.71
- Human Oral Bioavailability 20%
- Bioavailable
- Human Intestinal Absorption
- Absorbed
- Madin-Darby Canine Kidney
- -4.660
- Human Oral Bioavailability 50%
- Non-Bioavailable
- P-Glycoprotein Inhibitor
- Non-Inhibitor
- P-Glycoprotein Substrate
- Non-Substrate
- Skin Permeability
- -1.21
Distribution
- Blood-Brain Barrier (CNS)
- -
- Blood-Brain Barrier
- Non-Penetrable
- Fraction Unbound (Human)
- 1.170
- Plasma Protein Binding
- 53.91
- 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
- Inhibitor
- CYP 2D6 Substrate
- Non-Substrate
- CYP 3A4 Inhibitor
- Inhibitor
- CYP 3A4 Substrate
- Non-Substrate
- OATP1B1
- Non-Inhibitor
- OATP1B3
- Non-Inhibitor
Excretion
- Clearance
- 2.450
- Organic Cation Transporter 2
- Non-Inhibitor
- Half-Life of Drug
- -
Toxicity
- AMES Mutagenesis
- Toxic
- Avian
- Safe
- Bee
- Toxic
- Bioconcentration Factor
- 1.280
- Biodegradation
- Safe
- Carcinogenesis
- Toxic
- Crustacean
- Toxic
- Liver Injury I (DILI)
- Toxic
- Eye Corrosion
- Safe
- Eye Irritation
- Safe
- Maximum Tolerated Dose
- 0.270
- Liver Injury II
- Toxic
- hERG Blockers
- Safe
- Daphnia Maga
- 4.130
- 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
- 3.670
- Rat (Acute)
- 2.370
- Rat (Chronic Oral)
- 2.290
- Fathead Minnow
- 4.800
- Respiratory Disease
- Toxic
- Skin Sensitisation
- Safe
- SR-ARE
- Toxic
- SR-ATAD5
- Safe
- SR-HSE
- Safe
- SR-MMP
- Toxic
- SR-p53
- Safe
General Properties
- Boiling Point
- 458.270
- Hydration Free Energy
- -11.310
- Log(D) at pH=7.4
- 2.900
- Log(P)
- 3.52
- Log S
- -4.85
- Log(Vapor Pressure)
- -8.52
- Melting Point
- 268.41
- pKa Acid
- 7.55
- pKa Basic
- 7.11
| Protein Name | UniProt ID | Entry Name | Species | #Pharmacophore Points | Probability (0.7 ≤ Tversky Score ≤ 1.0) |
|---|---|---|---|---|---|
| Fibroblast growth factor receptor 1 | P11362 | FGFR1_HUMAN | Homo sapiens | 3 | 0.8835 |
| Capsid protein | Q9WBP8 | Q9WBP8_9VIRU | Adeno-associated virus - 1 | 3 | 0.8692 |
| 3',5'-cyclic-AMP phosphodiesterase 4D | Q08499 | PDE4D_HUMAN | Homo sapiens | 3 | 0.8197 |
| Fibroblast growth factor receptor 2 | P21802 | FGFR2_HUMAN | Homo sapiens | 3 | 0.8131 |
| Fibroblast growth factor receptor 2 | P21802 | FGFR2_HUMAN | Homo sapiens | 3 | 0.8117 |
| Ribosyldihydronicotinamide dehydrogenase [quinone] | P16083 | NQO2_HUMAN | Homo sapiens | 3 | 0.7860 |
| Beta-secretase 1 | P56817 | BACE1_HUMAN | Homo sapiens | 3 | 0.7853 |
| Alpha-ketoglutarate-dependent dioxygenase FTO | Q9C0B1 | FTO_HUMAN | Homo sapiens | 3 | 0.7804 |
| Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 3 | 0.7650 |
| Serine/threonine-protein kinase SKY1 | Q03656 | SKY1_YEAST | Saccharomyces cerevisiae | 3 | 0.7460 |
| High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A | O76083 | PDE9A_HUMAN | Homo sapiens | 4 | 0.7402 |
| GCN5-related N-acetyltransferase | B1YEL6 | B1YEL6_EXIS2 | Exiguobacterium sibiricum | 3 | 0.7297 |
| Lactoperoxidase | P80025 | PERL_BOVIN | Bos taurus | 3 | 0.7290 |
| Nuclear receptor ROR-gamma | P51449 | RORG_HUMAN | Homo sapiens | 3 | 0.7186 |
| Phosphodiesterase | Q53I60 | Q53I60_TRYCR | Trypanosoma cruzi | 4 | 0.7158 |
| Streptogramin A acetyltransferase | P50870 | VATD_ENTFC | Enterococcus faecium | 3 | 0.7115 |
| Lethal(3)malignant brain tumor-like protein 1 | Q9Y468 | LMBL1_HUMAN | Homo sapiens | 3 | 0.7106 |
| Lactotransferrin | P24627 | TRFL_BOVIN | Bos taurus | 2 | 0.7100 |
| Vitamin D-binding protein | P02774 | VTDB_HUMAN | Homo sapiens | 2 | 0.7096 |
| Casein kinase II subunit alpha | P68400 | CSK21_HUMAN | Homo sapiens | 4 | 0.7093 |
| Basic phospholipase A2 VRV-PL-VIIIa | P59071 | PA2B8_DABRR | Daboia russelii | 3 | 0.7068 |
| Ephrin type-B receptor 2 | P54763 | EPHB2_MOUSE | Mus musculus | 3 | 0.7065 |
| Diphtheria toxin | P00588 | DTX_CORBE | Corynephage beta | 3 | 0.7055 |
| Glutamate racemase | Q9ZLT0 | MURI_HELPJ | Helicobacter pylori | 3 | 0.7013 |