ANPDB

Select a section from the left sidebar

Citpressine II

Family: Plantae - Rutaceae
Kingdom: Plantae
Class: Alkaloid
- Subclass: Acridone Alkaloid

Canonical Smiles	COc1cc(O)c2c(c1)n(C)c1c(c2=O)ccc(c1OC)OC
InChI	InChI=1S/C17H17NO5/c1-18-11-7-9(21-2)8-12(19)14(11)16(20)10-5-6-13(22-3)17(23-4)15(10)18/h5-8,19H,1-4H3
InChIKey	CHCYJKZBXNSGCG-UHFFFAOYSA-N
Formula	C₁₇H₁₇NO₅
HBA	6
HBD	1
MW	315.33
Rotatable Bonds	3
TPSA	69.92
LogP	2.42
Number Rings	3
Number Aromatic Rings	3
Heavy Atom Count	23
Formal Charge	0
Fraction CSP3	0.24
Exact Mass	315.11
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

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: 5494828

Cas: 81525-59-9

Zinc: ZINC000014725178

Chebi: 172546

Nmrshiftdb2: 60076647

No compound-protein relationship available.

SMILES: c1cccc(c12)[nH]c3c(c2=O)cccc3

Level: 0

Mol. Weight: 315.33 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp): -4.55
Human Oral Bioavailability 20%: Bioavailable
Human Intestinal Absorption: Absorbed
Madin-Darby Canine Kidney: -4.530
Human Oral Bioavailability 50%: Bioavailable
P-Glycoprotein Inhibitor: Inhibitor
P-Glycoprotein Substrate: Non-Substrate
Skin Permeability: -2.02

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Penetrable
Fraction Unbound (Human): 1.350
Plasma Protein Binding: 61.62
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: Non-Substrate
CYP 2C9 Inhibitor: Non-Inhibitor
CYP 2C9 Substrate: Substrate
CYP 2D6 Inhibitor: Non-Inhibitor
CYP 2D6 Substrate: Non-Substrate
CYP 3A4 Inhibitor: Inhibitor
CYP 3A4 Substrate: Non-Substrate
OATP1B1: Non-Inhibitor
OATP1B3: Non-Inhibitor

Excretion

Clearance: 3.250
Organic Cation Transporter 2: Non-Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Toxic
Avian: Safe
Bee: Toxic
Bioconcentration Factor: 1.490
Biodegradation: Safe
Carcinogenesis: Safe
Crustacean: Toxic
Liver Injury I (DILI): Toxic
Eye Corrosion: Safe
Eye Irritation: Safe
Maximum Tolerated Dose: 0.300
Liver Injury II: Toxic
hERG Blockers: Safe
Daphnia Maga: 4.560
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: 3.420
Rat (Acute): 2.230
Rat (Chronic Oral): 2.430
Fathead Minnow: 5.000
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: 432.260
Hydration Free Energy: -9.670
Log(D) at pH=7.4: 2.420
Log(P): 2.2
Log S: -4.12
Log(Vapor Pressure): -7.08
Melting Point: 207.13
pKa Acid: 7.12
pKa Basic: 4.62

Protein Name	UniProt ID	Entry Name	Species	#Pharmacophore Points	Probability (0.7 ≤ Tversky Score ≤ 1.0)
Riboflavin synthase	P0AFU8	RISA_ECOLI	Escherichia coli	4	0.9591
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A	Q9Y233	PDE10_HUMAN	Homo sapiens	3	0.9345
Phenazine biosynthesis protein A/B	Q396C9	Q396C9_BURL3	Burkholderia lata	3	0.9209
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.9172
Tetracycline repressor protein class H	P51561	TETR8_PASMD	Pasteurella multocida	3	0.9070
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.8909
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.8724
Toxoflavin degrading enzyme	E3SET7	E3SET7_PAEPO	Paenibacillus polymyxa	3	0.8717
Tyrosine-protein kinase JAK2	O60674	JAK2_HUMAN	Homo sapiens	3	0.8668
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.8596
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase	Q9TQS6	DHDH_MACFA	Macaca fascicularis	3	0.8514
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.8487
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	3	0.8469
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	4	0.8424
Alpha-ketoglutarate-dependent dioxygenase FTO	Q9C0B1	FTO_HUMAN	Homo sapiens	3	0.8279
Bromodomain-containing protein 4	O60885	BRD4_HUMAN	Homo sapiens	3	0.8261
2-phospho-L-lactate transferase	Q8PVT6	COFD_METMA	Methanosarcina mazei	3	0.8207
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.8202
Mitogen-activated protein kinase 10	P53779	MK10_HUMAN	Homo sapiens	3	0.8192
Gentisate 1,2-dioxygenase	Q67FT0	Q67FT0_PSESE	Pseudaminobacter salicylatoxidans	3	0.8158
Kynurenine 3-monooxygenase	P38169	KMO_YEAST	Saccharomyces cerevisiae	3	0.8145
Bromodomain-containing protein 2	P25440	BRD2_HUMAN	Homo sapiens	3	0.8122
Methionine aminopeptidase 2	P9WK19	MAP12_MYCTU	Mycobacterium tuberculosis	3	0.8111
histidine kinase	O32393	O32393_ARTPT	Arthrospira platensis	3	0.8067
Biflaviolin synthase CYP158A2	Q9FCA6	C1582_STRCO	Streptomyces coelicolor / M145)	3	0.8048
Casein kinase II subunit alpha	P68400	CSK21_HUMAN	Homo sapiens	3	0.8011
Thymidine kinase	P0DTH5	KITH_HHV11	Human herpesvirus 1	3	0.8011
Photosynthetic reaction center cytochrome c subunit	P07173	CYCR_BLAVI	Blastochloris viridis	3	0.8002
Cysteine desulfurase IscS 2	O29689	ISCS2_ARCFU	Archaeoglobus fulgidus	3	0.7982
Bromodomain-containing protein 4	O60885	BRD4_HUMAN	Homo sapiens	3	0.7978
Catechol O-methyltransferase	P22734	COMT_RAT	Rattus norvegicus	3	0.7972
Lactoylglutathione lyase	Q9CPU0	LGUL_MOUSE	Mus musculus	2	0.7968
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.7966
Soluble acetylcholine receptor	Q8WSF8	Q8WSF8_APLCA	Aplysia californica	3	0.7936
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.7838
Serine/threonine-protein kinase pim-1	P11309	PIM1_HUMAN	Homo sapiens	3	0.7823
Metallo-beta-lactamase type 2	P26918	BLAB_AERHY	Aeromonas hydrophila	3	0.7788
Fatty acid-binding protein, intestinal	P12104	FABPI_HUMAN	Homo sapiens	3	0.7770
Succinate dehydrogenase flavoprotein subunit	P0AC41	SDHA_ECOLI	Escherichia coli	3	0.7768
Tubulin alpha-1B chain	P81947	TBA1B_BOVIN	Bos taurus	3	0.7726
11-beta-hydroxysteroid dehydrogenase 1	P28845	DHI1_HUMAN	Homo sapiens	4	0.7705
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.7701
Biflaviolin synthase CYP158A2	Q9FCA6	C1582_STRCO	Streptomyces coelicolor / M145)	3	0.7701
Tetracycline repressor protein class D	P0ACT4	TETR4_ECOLX	Escherichia coli	3	0.7671
ActVA 6 protein	Q53908	Q53908_STRCH	Streptomyces coelicolor	3	0.7664
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	4	0.7638
Catechol O-methyltransferase	P22734	COMT_RAT	Rattus norvegicus	3	0.7626
Casein kinase I isoform gamma-3	Q9Y6M4	KC1G3_HUMAN	Homo sapiens	3	0.7609
NmrA-like family domain-containing protein 1	Q9HBL8	NMRL1_HUMAN	Homo sapiens	3	0.7607
Transcriptional regulator, PadR-like family	A2RI36	A2RI36_LACLM	Lactococcus lactis subsp. cremoris	2	0.7597
Casein kinase II subunit alpha	P68400	CSK21_HUMAN	Homo sapiens	3	0.7534
Lactotransferrin	P24627	TRFL_BOVIN	Bos taurus	2	0.7481
cGMP-dependent 3',5'-cyclic phosphodiesterase	O00408	PDE2A_HUMAN	Homo sapiens	2	0.7477
Putative protease I	Q8A8A4	Q8A8A4_BACTN	Bacteroides thetaiotaomicron	2	0.7476
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	2	0.7474
Methionine aminopeptidase	P0AE18	MAP1_ECOLI	Escherichia coli	3	0.7462
Aldo-keto reductase family 1 member B1	P15121	ALDR_HUMAN	Homo sapiens	3	0.7430
Tubulin alpha chain	D0VWZ0	D0VWZ0_SHEEP	Ovis aries	3	0.7381
Glutamate receptor ionotropic, kainate 1	P22756	GRIK1_RAT	Rattus norvegicus	3	0.7333
Steroid Delta-isomerase	P07445	SDIS_PSEPU	Pseudomonas putida	3	0.7325
CCA-adding enzyme	O28126	CCA_ARCFU	Archaeoglobus fulgidus	2	0.7274
4-chlorobenzoyl CoA ligase	Q8GN86	Q8GN86_9BURK	Alcaligenes sp. AL3007	3	0.7264
Ribosyldihydronicotinamide dehydrogenase [quinone]	P16083	NQO2_HUMAN	Homo sapiens	3	0.7251
Prostaglandin G/H synthase 1	P05979	PGH1_SHEEP	Ovis aries	3	0.7218
Pteridine reductase 1	Q01782	PTR1_LEIMA	Leishmania major	2	0.7218
Protein ppBat	Q8A8A4	Q8A8A4_BACTN	Bacteroides thetaiotaomicron VPI-5482	2	0.7213
Orotate phosphoribosyltransferase	P08870	PYRE_SALTY	Salmonella typhimurium	3	0.7212
Orotidine 5'-phosphate decarboxylase	O58462	PYRF_PYRHO	Pyrococcus horikoshii	3	0.7202
NmrA-like family domain-containing protein 1	Q9HBL8	NMRL1_HUMAN	Homo sapiens	3	0.7198
Casein kinase II subunit alpha	P28523	CSK2A_MAIZE	Zea mays	3	0.7197
Pyridoxal kinase	P82197	PDXK_SHEEP	Ovis aries	4	0.7189
Beta-galactoside-specific lectin 4	Q6ITZ3	ML4_VISAL	Viscum album	2	0.7185
ActVA 6 protein	Q53908	Q53908_STRCH	Streptomyces coelicolor	3	0.7183
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	2	0.7156
Cyclin-dependent kinase 2	P24941	CDK2_HUMAN	Homo sapiens	3	0.7145
Pancreatic alpha-amylase	P04746	AMYP_HUMAN	Homo sapiens	2	0.7142
Tyrosine-protein kinase Lck	P06239	LCK_HUMAN	Homo sapiens	3	0.7141
Focal adhesion kinase 1	Q00944	FAK1_CHICK	Gallus gallus	3	0.7137
Cyclin-dependent kinase 2	P24941	CDK2_HUMAN	Homo sapiens	3	0.7133
Genome polyprotein	O92972	POLG_HCVJ4	Hepatitis C virus genotype 1b	3	0.7123
Focal adhesion kinase 1	Q00944	FAK1_CHICK	Gallus gallus	3	0.7122
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.7109
Bromodomain-containing protein 4	O60885	BRD4_HUMAN	Homo sapiens	4	0.7087
Aldo-keto reductase family 1 member B1	P80276	ALDR_PIG	Sus scrofa	3	0.7086
Serine/threonine-protein kinase Chk1	O14757	CHK1_HUMAN	Homo sapiens	3	0.7082
Cyclin-dependent kinase 2	P24941	CDK2_HUMAN	Homo sapiens	3	0.7070
Aldo-keto reductase family 1 member B1	P15121	ALDR_HUMAN	Homo sapiens	3	0.7064
Phenazine biosynthesis protein A/B	Q396C9	Q396C9_BURL3	Burkholderia lata	3	0.7060
TDP-4-oxo-6-deoxy-alpha-D-glucose-3,4-oxoisomerase	Q6T1W8	FDTA_ANETH	Aneurinibacillus thermoaerophilus	3	0.7032
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A	O76083	PDE9A_HUMAN	Homo sapiens	2	0.7023
Serine/threonine-protein kinase 24	Q9Y6E0	STK24_HUMAN	Homo sapiens	3	0.7015
Gag-Pol polyprotein	P03366	POL_HV1B1	Human immunodeficiency virus type 1 group M subtype B	3	0.7014
Streptavidin	P22629	SAV_STRAV	Streptomyces avidinii	3	0.7010
Activin receptor type-1	Q04771	ACVR1_HUMAN	Homo sapiens	3	0.7000

Download SDF