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Citracridone I
- Family: Plantae - Rutaceae
- Kingdom: Plantae
-
Class: Alkaloid
- Subclass: Acridone Alkaloid
| Canonical Smiles | COc1c(O)ccc2c1n(C)c1c(c2=O)c(O)cc2c1C=CC(O2)(C)C |
|---|---|
| InChI | InChI=1S/C20H19NO5/c1-20(2)8-7-10-14(26-20)9-13(23)15-16(10)21(3)17-11(18(15)24)5-6-12(22)19(17)25-4/h5-9,22-23H,1-4H3 |
| InChIKey | DIDVBISMWJGFOF-UHFFFAOYSA-N |
| Formula | C20H19NO5 |
| HBA | 6 |
| HBD | 2 |
| MW | 353.37 |
| Rotatable Bonds | 1 |
| TPSA | 80.92 |
| LogP | 3.3 |
| Number Rings | 4 |
| Number Aromatic Rings | 3 |
| Heavy Atom Count | 26 |
| Formal Charge | 0 |
| Fraction CSP3 | 0.25 |
| Exact Mass | 353.13 |
| 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 × paradisi | Rutaceae | Plantae | 37656 |
| 4 | Citrus reticulata | Rutaceae | Plantae | 85571 |
| 5 | Citrus x paradisi | Rutaceae | Plantae | 37656 |
Showing of synonyms
Citracridone I
Citracridone-I
A6PVJ9XP6K
6,10-dihydroxy-11-methoxy-3,3,12-trimethylpyrano[2,3-c]acridin-7-one
DTXSID40231179
11-METHOXY-3,3,12-TRIMETHYL-6,10-BIS(OXIDANYL)PYRANO(2,3-C)ACRIDIN-7-ONE
3,12-DIHYDRO-6,10-DIHYDROXY-11-METHOXY-3,3,12-TRIMETHYL-7H-PYRANO(2,3-C)ACRIDIN-7-ONE
7,11-DIHYDROXY-6-METHOXY-2,2,5-TRIMETHYL-5,10-DIHYDRO-2H-1-OXA-5-AZATETRAPHEN-10-ONE
6,10-dihydroxy-11-methoxy-3,3,12-trimethylpyrano(2,3-c)acridin-7-one
DTXCID90153670
Citra-I
81525-61-3
7H-Pyrano(2,3-c)acridin-7-one, 3,12-dihydro-6,10-dihydroxy-11-methoxy-3,3,12-trimethyl-
7H-Pyrano[2,3-c]acridin-7-one, 3,12-dihydro-6,10-dihydroxy-11-methoxy-3,3,12-trimethyl-
UNII-A6PVJ9XP6K
CHEMBL451706
CHEBI:174755
6,10-dihydroxy-11-methoxy-3,3,12-trimethyl-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]
- 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]
- Noulala CGT, Ouete JLN, et al. (2023). Coumarinolignoid and Indole Alkaloids from the Roots of the Hybrid Plant Citrus × paradisi Macfad (Rutaceae). Molecules. 2023, 28(3), 1078. [View] [PubMed]
- 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:
5487591
Cas:
81525-61-3
Chebi:
174755
Nmrshiftdb2:
60076642
Chembl:
CHEMBL451706
Comptox:
DTXSID40231179
No compound-protein relationship available.
SMILES: C1=CCOc(cc2)c1c(c23)[nH]c4c(c3=O)cccc4
Level: 0
Mol. Weight: 353.37 g/mol
Anti-diabetic
Anti-inflammatory
Antioxidant
Cytotoxic
Absorption
- Caco-2 (logPapp)
- -4.7
- Human Oral Bioavailability 20%
- Bioavailable
- Human Intestinal Absorption
- Absorbed
- Madin-Darby Canine Kidney
- -4.760
- Human Oral Bioavailability 50%
- Bioavailable
- P-Glycoprotein Inhibitor
- Non-Inhibitor
- P-Glycoprotein Substrate
- Non-Substrate
- Skin Permeability
- -1.36
Distribution
- Blood-Brain Barrier (CNS)
- -
- Blood-Brain Barrier
- Non-Penetrable
- Fraction Unbound (Human)
- 1.350
- Plasma Protein Binding
- 57.49
- 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
- 4.720
- Organic Cation Transporter 2
- Inhibitor
- Half-Life of Drug
- -
Toxicity
- AMES Mutagenesis
- Toxic
- Avian
- Safe
- Bee
- Toxic
- Bioconcentration Factor
- 1.230
- Biodegradation
- Safe
- Carcinogenesis
- Safe
- Crustacean
- Toxic
- Liver Injury I (DILI)
- Toxic
- Eye Corrosion
- Safe
- Eye Irritation
- Safe
- Maximum Tolerated Dose
- 0.110
- Liver Injury II
- Toxic
- hERG Blockers
- Safe
- Daphnia Maga
- 4.330
- 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
- 1.500
- Rat (Acute)
- 2.400
- Rat (Chronic Oral)
- 2.290
- Fathead Minnow
- 4.920
- 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
- 474.940
- Hydration Free Energy
- -9.900
- Log(D) at pH=7.4
- 2.680
- Log(P)
- 3.47
- Log S
- -4.81
- Log(Vapor Pressure)
- -8.22
- Melting Point
- 275.64
- pKa Acid
- 8.38
- pKa Basic
- 6.54
| Protein Name | UniProt ID | Entry Name | Species | #Pharmacophore Points | Probability (0.7 ≤ Tversky Score ≤ 1.0) |
|---|---|---|---|---|---|
| Cytosolic purine 5'-nucleotidase | P49902 | 5NTC_HUMAN | Homo sapiens | 3 | 0.8943 |
| Capsid protein | Q9WBP8 | Q9WBP8_9VIRU | Adeno-associated virus - 1 | 3 | 0.8579 |
| Lactoylglutathione lyase | Q9CPU0 | LGUL_MOUSE | Mus musculus | 3 | 0.8256 |
| 3',5'-cyclic-AMP phosphodiesterase 4D | Q08499 | PDE4D_HUMAN | Homo sapiens | 3 | 0.8192 |
| Serine/threonine-protein kinase SKY1 | Q03656 | SKY1_YEAST | Saccharomyces cerevisiae | 3 | 0.8143 |
| Ferrochelatase, mitochondrial | P22830 | HEMH_HUMAN | Homo sapiens | 3 | 0.7973 |
| Beta-secretase 1 | P56817 | BACE1_HUMAN | Homo sapiens | 3 | 0.7915 |
| Alpha-ketoglutarate-dependent dioxygenase FTO | Q9C0B1 | FTO_HUMAN | Homo sapiens | 3 | 0.7847 |
| Beta-secretase 1 | P56817 | BACE1_HUMAN | Homo sapiens | 3 | 0.7827 |
| Fibroblast growth factor receptor 2 | P21802 | FGFR2_HUMAN | Homo sapiens | 3 | 0.7782 |
| Casein kinase II subunit alpha | P68400 | CSK21_HUMAN | Homo sapiens | 3 | 0.7763 |
| Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 3 | 0.7714 |
| Fibroblast growth factor receptor 2 | P21802 | FGFR2_HUMAN | Homo sapiens | 3 | 0.7696 |
| Polymerase acidic protein | C3W5S0 | C3W5S0_I09A0 | Influenza A virus | 3 | 0.7565 |
| Catechol O-methyltransferase | P22734 | COMT_RAT | Rattus norvegicus | 3 | 0.7520 |
| Basic phospholipase A2 VRV-PL-VIIIa | P59071 | PA2B8_DABRR | Daboia russelii | 2 | 0.7465 |
| Casein kinase II subunit alpha | P68400 | CSK21_HUMAN | Homo sapiens | 3 | 0.7420 |
| High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A | O76083 | PDE9A_HUMAN | Homo sapiens | 4 | 0.7369 |
| Casein kinase II subunit alpha | P68400 | CSK21_HUMAN | Homo sapiens | 3 | 0.7327 |
| Cytochrome P450 monooxygenase | Q5YNS8 | Q5YNS8_NOCFA | Nocardia farcinica | 3 | 0.7298 |
| 3-hydroxy-3-methylglutaryl-coenzyme A reductase | P04035 | HMDH_HUMAN | Homo sapiens | 3 | 0.7268 |
| Casein kinase II subunit alpha | P68400 | CSK21_HUMAN | Homo sapiens | 3 | 0.7258 |
| Basic phospholipase A2 VRV-PL-VIIIa | P59071 | PA2B8_DABRR | Daboia russelii | 2 | 0.7205 |
| Basic phospholipase A2 VRV-PL-VIIIa | P59071 | PA2B8_DABRR | Daboia russelii | 3 | 0.7182 |
| Phosphodiesterase | Q53I60 | Q53I60_TRYCR | Trypanosoma cruzi | 4 | 0.7178 |
| Serine/threonine-protein kinase pim-1 | P11309 | PIM1_HUMAN | Homo sapiens | 3 | 0.7171 |
| Ephrin type-B receptor 2 | P54763 | EPHB2_MOUSE | Mus musculus | 3 | 0.7134 |
| Streptogramin A acetyltransferase | P50870 | VATD_ENTFC | Enterococcus faecium | 3 | 0.7109 |
| Glutamate racemase | Q9ZLT0 | MURI_HELPJ | Helicobacter pylori | 3 | 0.7029 |