Citracridone II - Compound Card

Citracridone II

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Citracridone II

Structure
Zoomed Structure
  • Family: Plantae - Rutaceae
  • Kingdom: Plantae
  • Class: Alkaloid
    • Subclass: Acridone Alkaloid
Canonical Smiles COc1c(OC)ccc2c1n(C)c1c(c2=O)c(O)cc2c1C=CC(O2)(C)C
InChI InChI=1S/C21H21NO5/c1-21(2)9-8-11-15(27-21)10-13(23)16-17(11)22(3)18-12(19(16)24)6-7-14(25-4)20(18)26-5/h6-10,23H,1-5H3
InChIKey OBCBNXMEAJGWOD-UHFFFAOYSA-N
Formula C21H21NO5
HBA 6
HBD 1
MW 367.4
Rotatable Bonds 2
TPSA 69.92
LogP 3.6
Number Rings 4
Number Aromatic Rings 3
Heavy Atom Count 27
Formal Charge 0
Fraction CSP3 0.29
Exact Mass 367.14
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Citrus aurantium Rutaceae Plantae 43166
2 Citrus × paradisi Rutaceae Plantae 37656
3 Citrus x paradisi Rutaceae Plantae 37656

Showing of synonyms

  • 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]
Pubchem: 5494832
Nmrshiftdb2: 60076641

No compound-protein relationship available.

Structure

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

Level: 0

Mol. Weight: 367.4 g/mol

Cytotoxic

Absorption

Caco-2 (logPapp)
-4.63
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.540
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-1.7

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
1.400
Plasma Protein Binding
59.79
Steady State Volume of Distribution
-

Metabolism

Breast Cancer Resistance Protein
Inhibitor
CYP 1A2 Inhibitor
Inhibitor
CYP 1A2 Substrate
Substrate
CYP 2C19 Inhibitor
Inhibitor
CYP 2C19 Substrate
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
4.640
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Toxic
Bioconcentration Factor
1.540
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Toxic
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.160
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
4.640
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
-1.370
Rat (Acute)
2.620
Rat (Chronic Oral)
2.090
Fathead Minnow
5.150
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
480.750
Hydration Free Energy
-7.820
Log(D) at pH=7.4
2.740
Log(P)
3.44
Log S
-4.56
Log(Vapor Pressure)
-8.09
Melting Point
225.82
pKa Acid
7.37
pKa Basic
6.57
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8748
Capsid protein Q9WBP8 Q9WBP8_9VIRU Adeno-associated virus - 1 3 0.8602
ATP-dependent molecular chaperone HSP82 P02829 HSP82_YEAST Saccharomyces cerevisiae 3 0.8355
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 3 0.8321
Bromodomain-containing protein 2 P25440 BRD2_HUMAN Homo sapiens 3 0.8249
LIM domain kinase 1 P53667 LIMK1_HUMAN Homo sapiens 3 0.8185
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.8127
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 3 0.8084
Alpha-ketoglutarate-dependent dioxygenase FTO Q9C0B1 FTO_HUMAN Homo sapiens 3 0.8079
Serine/threonine-protein kinase SKY1 Q03656 SKY1_YEAST Saccharomyces cerevisiae 3 0.8076
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.8011
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7970
MAP kinase-activated protein kinase 2 P49137 MAPK2_HUMAN Homo sapiens 3 0.7957
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 3 0.7916
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 3 0.7870
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.7867
Thymidine kinase P0DTH5 KITH_HHV11 Human herpesvirus 1 3 0.7866
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.7858
Catechol O-methyltransferase P22734 COMT_RAT Rattus norvegicus 3 0.7700
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase F6MZ55 F6MZ55_9FIRM Sporomusa ovata 3 0.7664
Aldo-keto reductase family 1 member B1 P15121 ALDR_HUMAN Homo sapiens 2 0.7657
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.7640
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.7632
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.7612
Phosphodiesterase Q53I60 Q53I60_TRYCR Trypanosoma cruzi 4 0.7549
Cytochrome P450 monooxygenase Q5YNS8 Q5YNS8_NOCFA Nocardia farcinica 3 0.7503
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7454
Retinaldehyde-binding protein 1 P12271 RLBP1_HUMAN Homo sapiens 4 0.7437
Ephrin type-B receptor 2 P54763 EPHB2_MOUSE Mus musculus 3 0.7432
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 4 0.7412
Catechol O-methyltransferase P22734 COMT_RAT Rattus norvegicus 3 0.7406
Retinol dehydratase Q26490 Q26490_SPOFR Spodoptera frugiperda 3 0.7391
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 3 0.7378
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7378
Peripheral plasma membrane protein CASK O14936 CSKP_HUMAN Homo sapiens 3 0.7334
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.7316
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 4 0.7293
Nuclear receptor subfamily 1 group I member 2 O75469 NR1I2_HUMAN Homo sapiens 3 0.7256
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7240
Lethal(3)malignant brain tumor-like protein 1 Q9Y468 LMBL1_HUMAN Homo sapiens 3 0.7226
11-beta-hydroxysteroid dehydrogenase 1 P28845 DHI1_HUMAN Homo sapiens 4 0.7224
Nuclear receptor ROR-gamma P51449 RORG_HUMAN Homo sapiens 3 0.7222
ActVA 6 protein Q53908 Q53908_STRCH Streptomyces coelicolor 3 0.7214
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.7157
2-phospho-L-lactate transferase Q8PVT6 COFD_METMA Methanosarcina mazei 3 0.7156
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 3 0.7146
Cyclin-dependent kinase 9 P50750 CDK9_HUMAN Homo sapiens 3 0.7145
Serine/threonine-protein kinase pim-1 P11309 PIM1_HUMAN Homo sapiens 3 0.7141
Aldo-keto reductase family 1 member B1 P80276 ALDR_PIG Sus scrofa 3 0.7117
Streptogramin A acetyltransferase P50870 VATD_ENTFC Enterococcus faecium 3 0.7107
Lactoperoxidase P80025 PERL_BOVIN Bos taurus 3 0.7074
S-adenosylmethionine decarboxylase proenzyme P17707 DCAM_HUMAN Homo sapiens 3 0.7057
Methionine aminopeptidase P0AE18 MAP1_ECOLI Escherichia coli 3 0.7033
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform O02697 PK3CG_PIG Sus scrofa 3 0.7013

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