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Citpressine I
- Family: Plantae - Rutaceae
- Kingdom: Plantae
-
Class: Alkaloid
- Subclass: Acridone Alkaloid
| Canonical Smiles | COc1cc(O)c2c(c1)n(C)c1c(c2=O)ccc(c1OC)O |
|---|---|
| InChI | InChI=1S/C16H15NO5/c1-17-10-6-8(21-2)7-12(19)13(10)15(20)9-4-5-11(18)16(22-3)14(9)17/h4-7,18-19H,1-3H3 |
| InChIKey | OQMSMWRXIZYYNR-UHFFFAOYSA-N |
| Formula | C16H15NO5 |
| HBA | 6 |
| HBD | 2 |
| MW | 301.3 |
| Rotatable Bonds | 2 |
| TPSA | 80.92 |
| LogP | 2.12 |
| Number Rings | 3 |
| Number Aromatic Rings | 3 |
| Heavy Atom Count | 22 |
| Formal Charge | 0 |
| Fraction CSP3 | 0.19 |
| Exact Mass | 301.1 |
| Number of Lipinski Rule Violations | 0 |
| # | Species | Family | Kingdom | NCBI Taxonomy ID |
|---|---|---|---|---|
| 1 | Citrus aurantium | Rutaceae | Plantae | 43166 |
| 2 | Citrus × paradisi | Rutaceae | Plantae | 37656 |
Showing of synonyms
Citpressine I
P3864YU5DK
1,6-dihydroxy-3,5-dimethoxy-10-methylacridin-9-one
CHEMBL-455602
1,6-Dihydroxy-3,5-dimethoxy-10-methyl-9(10H)-acridinone
9(10H)-Acridinone, 1,6-dihydroxy-3,5-dimethoxy-10-methyl-
3,5-Dimethoxy-10-methyl-1,6-bis(oxidanyl)acridin-9-one
1,6-Dihydroxy-3,5-dimethoxy-10-methylacridone
1,6-dihydroxy-3,5-dimethoxy-10-methyl-9,10-dihydroacridin-9-one
81525-58-8
UNII-P3864YU5DK
CHEMBL455602
CHEBI:168960
DTXSID301206276
1,6-dihydroxy-3,5-dimethoxy-10-methyl-acridin-9-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]
Pubchem:
5494827
Cas:
81525-58-8
Zinc:
ZINC000003801131
Chebi:
168960
Nmrshiftdb2:
60076649
Chembl:
CHEMBL455602
No compound-protein relationship available.
SMILES: c1cccc(c12)[nH]c3c(c2=O)cccc3
Level: 0
Mol. Weight: 301.3 g/mol
No bioactivities available.
Absorption
- Caco-2 (logPapp)
- -4.62
- Human Oral Bioavailability 20%
- Bioavailable
- Human Intestinal Absorption
- Absorbed
- Madin-Darby Canine Kidney
- -4.770
- Human Oral Bioavailability 50%
- Bioavailable
- P-Glycoprotein Inhibitor
- Non-Inhibitor
- P-Glycoprotein Substrate
- Non-Substrate
- Skin Permeability
- -1.79
Distribution
- Blood-Brain Barrier (CNS)
- -
- Blood-Brain Barrier
- Non-Penetrable
- Fraction Unbound (Human)
- 1.290
- Plasma Protein Binding
- 62.14
- 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
- Inhibitor
- CYP 3A4 Substrate
- Non-Substrate
- OATP1B1
- Non-Inhibitor
- OATP1B3
- Non-Inhibitor
Excretion
- Clearance
- 4.140
- Organic Cation Transporter 2
- Non-Inhibitor
- Half-Life of Drug
- -
Toxicity
- AMES Mutagenesis
- Toxic
- Avian
- Safe
- Bee
- Safe
- Bioconcentration Factor
- 1.280
- Biodegradation
- Safe
- Carcinogenesis
- Safe
- Crustacean
- Toxic
- Liver Injury I (DILI)
- Toxic
- Eye Corrosion
- Safe
- Eye Irritation
- Safe
- Maximum Tolerated Dose
- 0.550
- Liver Injury II
- Toxic
- hERG Blockers
- Safe
- Daphnia Maga
- 4.170
- Micronucleos
- Toxic
- NR-AhR
- Toxic
- 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
- 4.150
- Rat (Acute)
- 2.130
- Rat (Chronic Oral)
- 2.760
- Fathead Minnow
- 4.750
- Respiratory Disease
- Safe
- Skin Sensitisation
- Safe
- SR-ARE
- Toxic
- SR-ATAD5
- Safe
- SR-HSE
- Safe
- SR-MMP
- Toxic
- SR-p53
- Toxic
General Properties
- Boiling Point
- 438.060
- Hydration Free Energy
- -9.720
- Log(D) at pH=7.4
- 2.250
- Log(P)
- 2.26
- Log S
- -4.43
- Log(Vapor Pressure)
- -7.31
- Melting Point
- 256.89
- pKa Acid
- 7.65
- pKa Basic
- 5.86
| Protein Name | UniProt ID | Entry Name | Species | #Pharmacophore Points | Probability (0.7 ≤ Tversky Score ≤ 1.0) |
|---|---|---|---|---|---|
| Epidermal growth factor receptor | P00533 | EGFR_HUMAN | Homo sapiens | 3 | 0.9361 |
| Epidermal growth factor receptor | P00533 | EGFR_HUMAN | Homo sapiens | 3 | 0.9345 |
| Riboflavin synthase | P0AFU8 | RISA_ECOLI | Escherichia coli | 4 | 0.9311 |
| Cytosolic purine 5'-nucleotidase | P49902 | 5NTC_HUMAN | Homo sapiens | 3 | 0.9239 |
| Putative ketoacyl reductase | P16544 | ACT3_STRCO | Streptomyces coelicolor / M145) | 3 | 0.9143 |
| cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A | Q9Y233 | PDE10_HUMAN | Homo sapiens | 3 | 0.9119 |
| L-lactate dehydrogenase | Q27743 | LDH_PLAFD | Plasmodium falciparum | 3 | 0.9067 |
| Casein kinase II subunit alpha | P68400 | CSK21_HUMAN | Homo sapiens | 3 | 0.8950 |
| Casein kinase II subunit alpha | P68400 | CSK21_HUMAN | Homo sapiens | 3 | 0.8785 |
| Gentisate 1,2-dioxygenase | Q67FT0 | Q67FT0_PSESE | Pseudaminobacter salicylatoxidans | 3 | 0.8658 |
| Heat shock protein HSP 90-alpha | P07900 | HS90A_HUMAN | Homo sapiens | 3 | 0.8546 |
| Biflaviolin synthase CYP158A2 | Q9FCA6 | C1582_STRCO | Streptomyces coelicolor / M145) | 3 | 0.8517 |
| 3',5'-cyclic-AMP phosphodiesterase 4D | Q08499 | PDE4D_HUMAN | Homo sapiens | 3 | 0.8501 |
| Carbonic anhydrase 2 | P00918 | CAH2_HUMAN | Homo sapiens | 3 | 0.8377 |
| Biflaviolin synthase CYP158A2 | Q9FCA6 | C1582_STRCO | Streptomyces coelicolor / M145) | 3 | 0.8373 |
| histidine kinase | O32393 | O32393_ARTPT | Arthrospira platensis | 3 | 0.8169 |
| NmrA-like family domain-containing protein 1 | Q9HBL8 | NMRL1_HUMAN | Homo sapiens | 3 | 0.8145 |
| Tetracycline repressor protein class H | P51561 | TETR8_PASMD | Pasteurella multocida | 3 | 0.8142 |
| Albumin | P02768 | ALBU_HUMAN | Homo sapiens | 3 | 0.8137 |
| Acetylornithine/succinyldiaminopimelate aminotransferase | P40732 | ARGD_SALTY | Salmonella typhimurium | 3 | 0.8038 |
| 2-phospho-L-lactate transferase | Q8PVT6 | COFD_METMA | Methanosarcina mazei | 3 | 0.8011 |
| Alpha-ketoglutarate-dependent dioxygenase FTO | Q9C0B1 | FTO_HUMAN | Homo sapiens | 3 | 0.8004 |
| Serine/threonine-protein kinase pim-1 | P11309 | PIM1_HUMAN | Homo sapiens | 3 | 0.7991 |
| 3',5'-cyclic-AMP phosphodiesterase 4D | Q08499 | PDE4D_HUMAN | Homo sapiens | 3 | 0.7978 |
| Casein kinase II subunit alpha | P68400 | CSK21_HUMAN | Homo sapiens | 3 | 0.7936 |
| Polymerase acidic protein | C3W5S0 | C3W5S0_I09A0 | Influenza A virus | 3 | 0.7925 |
| Tyrosine-protein kinase JAK2 | O60674 | JAK2_HUMAN | Homo sapiens | 3 | 0.7877 |
| Toxoflavin degrading enzyme | E3SET7 | E3SET7_PAEPO | Paenibacillus polymyxa | 3 | 0.7855 |
| Epidermal growth factor receptor | P00533 | EGFR_HUMAN | Homo sapiens | 3 | 0.7818 |
| Basic phospholipase A2 VRV-PL-VIIIa | P59071 | PA2B8_DABRR | Daboia russelii | 4 | 0.7802 |
| Protoporphyrinogen oxidase, mitochondrial | O24164 | PPOM_TOBAC | Nicotiana tabacum | 3 | 0.7792 |
| Casein kinase II subunit alpha | P68400 | CSK21_HUMAN | Homo sapiens | 3 | 0.7788 |
| Proliferating cell nuclear antigen | P12004 | PCNA_HUMAN | Homo sapiens | 3 | 0.7759 |
| Casein kinase II subunit alpha | P68400 | CSK21_HUMAN | Homo sapiens | 3 | 0.7758 |
| Thymidine kinase | P0DTH5 | KITH_HHV11 | Human herpesvirus 1 | 3 | 0.7757 |
| Tetracycline repressor protein class D | P0ACT4 | TETR4_ECOLX | Escherichia coli | 3 | 0.7727 |
| NmrA-like family domain-containing protein 1 | Q9HBL8 | NMRL1_HUMAN | Homo sapiens | 3 | 0.7644 |
| Polymerase basic protein 2 | P31345 | PB2_I75A3 | Influenza A virus | 3 | 0.7624 |
| 3',5'-cyclic-AMP phosphodiesterase 4D | Q08499 | PDE4D_HUMAN | Homo sapiens | 3 | 0.7590 |
| Casein kinase I isoform gamma-3 | Q9Y6M4 | KC1G3_HUMAN | Homo sapiens | 3 | 0.7565 |
| F420-dependent NADP reductase | O29370 | FNO_ARCFU | Archaeoglobus fulgidus | 3 | 0.7549 |
| Homoserine dehydrogenase | P31116 | DHOM_YEAST | Saccharomyces cerevisiae | 3 | 0.7533 |
| Activin receptor type-1 | Q04771 | ACVR1_HUMAN | Homo sapiens | 3 | 0.7466 |
| ActVA 6 protein | Q53908 | Q53908_STRCH | Streptomyces coelicolor | 3 | 0.7457 |
| Kynurenine 3-monooxygenase | P38169 | KMO_YEAST | Saccharomyces cerevisiae | 3 | 0.7440 |
| 3-hydroxy-3-methylglutaryl-coenzyme A reductase | P04035 | HMDH_HUMAN | Homo sapiens | 3 | 0.7437 |
| APH(2'')-Id | O68183 | O68183_ENTCA | Enterococcus casseliflavus | 3 | 0.7436 |
| Glutamate receptor ionotropic, kainate 1 | P22756 | GRIK1_RAT | Rattus norvegicus | 3 | 0.7410 |
| Ribosomal small subunit pseudouridine synthase A | P0AA43 | RSUA_ECOLI | Escherichia coli | 3 | 0.7365 |
| Methionine aminopeptidase | P0AE18 | MAP1_ECOLI | Escherichia coli | 3 | 0.7359 |
| Methionine aminopeptidase 2 | P9WK19 | MAP12_MYCTU | Mycobacterium tuberculosis | 3 | 0.7317 |
| Tyrosine-protein kinase Lck | P06239 | LCK_HUMAN | Homo sapiens | 3 | 0.7314 |
| 3-phosphoinositide-dependent protein kinase 1 | O15530 | PDPK1_HUMAN | Homo sapiens | 3 | 0.7309 |
| Albumin | P02768 | ALBU_HUMAN | Homo sapiens | 3 | 0.7235 |
| Cyclin-dependent kinase 2 | P24941 | CDK2_HUMAN | Homo sapiens | 3 | 0.7232 |
| WxcM-like protein | Q12KT8 | Q12KT8_SHEDO | Shewanella denitrificans | 3 | 0.7230 |
| Dodecin | Q5SIE3 | DODEC_THET8 | Thermus thermophilus | 4 | 0.7226 |
| Death-associated protein kinase 3 | O43293 | DAPK3_HUMAN | Homo sapiens | 4 | 0.7200 |
| Metallo-beta-lactamase type 2 | P26918 | BLAB_AERHY | Aeromonas hydrophila | 3 | 0.7199 |
| Orotate phosphoribosyltransferase | P08870 | PYRE_SALTY | Salmonella typhimurium | 3 | 0.7195 |
| Serine/threonine-protein kinase pim-1 | P11309 | PIM1_HUMAN | Homo sapiens | 3 | 0.7185 |
| Ribosyldihydronicotinamide dehydrogenase [quinone] | P16083 | NQO2_HUMAN | Homo sapiens | 3 | 0.7184 |
| Basic phospholipase A2 VRV-PL-VIIIa | P59071 | PA2B8_DABRR | Daboia russelii | 3 | 0.7150 |
| Glycogen synthase kinase-3 beta | P49841 | GSK3B_HUMAN | Homo sapiens | 2 | 0.7150 |
| Gag-Pol polyprotein | P12497 | POL_HV1N5 | Human immunodeficiency virus type 1 group M subtype B | 3 | 0.7147 |
| Steroid Delta-isomerase | P07445 | SDIS_PSEPU | Pseudomonas putida | 3 | 0.7139 |
| Cysteine desulfurase IscS 2 | O29689 | ISCS2_ARCFU | Archaeoglobus fulgidus | 3 | 0.7137 |
| Pancreatic alpha-amylase | P04746 | AMYP_HUMAN | Homo sapiens | 2 | 0.7127 |
| Type IV / VI secretion system DotU domain-containing protein | Q9KN50 | Q9KN50_VIBCH | Vibrio cholerae serotype O1 | 2 | 0.7109 |
| Methionine aminopeptidase | P0AE18 | MAP1_ECOLI | Escherichia coli | 3 | 0.7100 |
| Lactotransferrin | P24627 | TRFL_BOVIN | Bos taurus | 2 | 0.7082 |
| Cathepsin S | P25774 | CATS_HUMAN | Homo sapiens | 3 | 0.7067 |
| Gag-Pol polyprotein | P03366 | POL_HV1B1 | Human immunodeficiency virus type 1 group M subtype B | 3 | 0.7055 |
| Enoyl-ACP reductase | Q9BJJ9 | Q9BJJ9_PLAFA | Plasmodium falciparum | 3 | 0.7055 |
| Fibroblast growth factor receptor 2 | P21802 | FGFR2_HUMAN | Homo sapiens | 2 | 0.7050 |
| Carminomycin 4-O-methyltransferase DnrK | Q06528 | DNRK_STRPE | Streptomyces peucetius | 3 | 0.7031 |
| High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A | O76083 | PDE9A_HUMAN | Homo sapiens | 2 | 0.7031 |
| Aldo-keto reductase family 1 member B1 | P15121 | ALDR_HUMAN | Homo sapiens | 2 | 0.7023 |
| Serine/threonine-protein kinase Chk1 | O14757 | CHK1_HUMAN | Homo sapiens | 3 | 0.7012 |