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Citruisinine II

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

Canonical Smiles	COc1c(OC)cc(c2c1n(C)c1c(c2=O)cccc1O)O
InChI	InChI=1S/C16H15NO5/c1-17-13-8(5-4-6-9(13)18)15(20)12-10(19)7-11(21-2)16(22-3)14(12)17/h4-7,18-19H,1-3H3
InChIKey	UTEAJHNFBCLZHN-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

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]

Pubchem: 5487772

Cas: 86680-32-2

Chebi: 184245

Nmrshiftdb2: 70003118

Chembl: CHEMBL451705

Comptox: DTXSID10235760

Bindingdb: 50336481

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): -4.57
Human Oral Bioavailability 20%: Bioavailable
Human Intestinal Absorption: Absorbed
Madin-Darby Canine Kidney: -4.720
Human Oral Bioavailability 50%: Bioavailable
P-Glycoprotein Inhibitor: Non-Inhibitor
P-Glycoprotein Substrate: Non-Substrate
Skin Permeability: -1.65

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Non-Penetrable
Fraction Unbound (Human): 1.290
Plasma Protein Binding: 62.91
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: 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: 2.950
Organic Cation Transporter 2: Non-Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Toxic
Avian: Safe
Bee: Toxic
Bioconcentration Factor: 1.430
Biodegradation: Safe
Carcinogenesis: Safe
Crustacean: Toxic
Liver Injury I (DILI): Toxic
Eye Corrosion: Safe
Eye Irritation: Safe
Maximum Tolerated Dose: 0.630
Liver Injury II: Toxic
hERG Blockers: Safe
Daphnia Maga: 4.200
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: 4.100
Rat (Acute): 2.130
Rat (Chronic Oral): 2.620
Fathead Minnow: 4.740
Respiratory Disease: Safe
Skin Sensitisation: Safe
SR-ARE: Toxic
SR-ATAD5: Safe
SR-HSE: Safe
SR-MMP: Toxic
SR-p53: Safe

General Properties

Boiling Point: 428.890
Hydration Free Energy: -10.010
Log(D) at pH=7.4: 2.250
Log(P): 2.03
Log S: -4.63
Log(Vapor Pressure): -7.14
Melting Point: 226.03
pKa Acid: 7.54
pKa Basic: 5.01

Protein Name	UniProt ID	Entry Name	Species	#Pharmacophore Points	Probability (0.7 ≤ Tversky Score ≤ 1.0)
Riboflavin synthase	P0AFU8	RISA_ECOLI	Escherichia coli	4	0.9484
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A	Q9Y233	PDE10_HUMAN	Homo sapiens	3	0.9236
Biflaviolin synthase CYP158A1	Q9KZF5	C1581_STRCO	Streptomyces coelicolor / M145)	3	0.9167
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.9024
Fibroblast growth factor receptor 1	P11362	FGFR1_HUMAN	Homo sapiens	3	0.8963
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.8793
LIM domain kinase 1	P53667	LIMK1_HUMAN	Homo sapiens	3	0.8716
Fibroblast growth factor receptor 2	P21802	FGFR2_HUMAN	Homo sapiens	3	0.8658
Corticosteroid-binding globulin	P08185	CBG_HUMAN	Homo sapiens	3	0.8653
Fibroblast growth factor receptor 2	P21802	FGFR2_HUMAN	Homo sapiens	3	0.8592
Norsolorinic acid synthase	Q12053	AFLC_ASPPU	Aspergillus parasiticus	3	0.8480
Tetracycline repressor protein class H	P51561	TETR8_PASMD	Pasteurella multocida	3	0.8471
Tyrosine-protein kinase JAK2	O60674	JAK2_HUMAN	Homo sapiens	3	0.8445
ActVA 6 protein	Q53908	Q53908_STRCH	Streptomyces coelicolor	4	0.8420
Serine/threonine-protein kinase SKY1	Q03656	SKY1_YEAST	Saccharomyces cerevisiae	3	0.8389
Succinate dehydrogenase flavoprotein subunit	P0AC41	SDHA_ECOLI	Escherichia coli	3	0.8357
Serine/threonine-protein kinase Chk1	O14757	CHK1_HUMAN	Homo sapiens	3	0.8350
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A	O76083	PDE9A_HUMAN	Homo sapiens	3	0.8306
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.8288
Mitogen-activated protein kinase 10	P53779	MK10_HUMAN	Homo sapiens	3	0.8257
Bromodomain-containing protein 4	O60885	BRD4_HUMAN	Homo sapiens	3	0.8234
Capsid protein	Q9WBP8	Q9WBP8_9VIRU	Adeno-associated virus - 1	3	0.8228
Casein kinase II subunit alpha	P68400	CSK21_HUMAN	Homo sapiens	3	0.8177
cGMP-dependent 3',5'-cyclic phosphodiesterase	O00408	PDE2A_HUMAN	Homo sapiens	3	0.8165
Toxoflavin degrading enzyme	E3SET7	E3SET7_PAEPO	Paenibacillus polymyxa	3	0.8145
3-phosphoinositide-dependent protein kinase 1	O15530	PDPK1_HUMAN	Homo sapiens	4	0.8108
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase	Q9TQS6	DHDH_MACFA	Macaca fascicularis	3	0.8088
Lactoylglutathione lyase	Q9CPU0	LGUL_MOUSE	Mus musculus	2	0.8053
ATP-dependent molecular chaperone HSP82	P02829	HSP82_YEAST	Saccharomyces cerevisiae	3	0.8047
Thymidine kinase	P0DTH5	KITH_HHV11	Human herpesvirus 1	3	0.8041
Alpha-ketoglutarate-dependent dioxygenase FTO	Q9C0B1	FTO_HUMAN	Homo sapiens	3	0.8018
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	3	0.7965
Methionine aminopeptidase 2	P9WK19	MAP12_MYCTU	Mycobacterium tuberculosis	3	0.7910
Sulfide-quinone reductase	B7JBP8	SQRD_ACIF2	Acidithiobacillus ferrooxidans)	3	0.7880
Biflaviolin synthase CYP158A2	Q9FCA6	C1582_STRCO	Streptomyces coelicolor / M145)	3	0.7864
Casein kinase II subunit alpha	P68400	CSK21_HUMAN	Homo sapiens	3	0.7863
Serine/threonine-protein kinase pim-1	P11309	PIM1_HUMAN	Homo sapiens	3	0.7811
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.7784
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.7767
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.7722
Catechol O-methyltransferase	P22734	COMT_RAT	Rattus norvegicus	3	0.7703
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	4	0.7702
Queuine tRNA-ribosyltransferase	P28720	TGT_ZYMMO	Zymomonas mobilis subsp. mobilis	3	0.7675
Casein kinase I isoform gamma-3	Q9Y6M4	KC1G3_HUMAN	Homo sapiens	3	0.7657
APH(2'')-Id	O68183	O68183_ENTCA	Enterococcus casseliflavus	4	0.7648
MAP kinase-activated protein kinase 2	P49137	MAPK2_HUMAN	Homo sapiens	3	0.7636
Ephrin type-B receptor 2	P54763	EPHB2_MOUSE	Mus musculus	3	0.7581
Transcriptional regulator, PadR-like family	A2RI36	A2RI36_LACLM	Lactococcus lactis subsp. cremoris	2	0.7556
Serine/threonine-protein kinase Chk1	O14757	CHK1_HUMAN	Homo sapiens	3	0.7525
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.7499
Putative protease I	Q8A8A4	Q8A8A4_BACTN	Bacteroides thetaiotaomicron	2	0.7494
Methionine aminopeptidase	P0AE18	MAP1_ECOLI	Escherichia coli	3	0.7488
Pteridine reductase 1	Q01782	PTR1_LEIMA	Leishmania major	3	0.7449
Lactotransferrin	P24627	TRFL_BOVIN	Bos taurus	2	0.7422
Aldo-keto reductase family 1 member C2	P52895	AK1C2_HUMAN	Homo sapiens	2	0.7415
Glycogen synthase kinase-3 beta	P49841	GSK3B_HUMAN	Homo sapiens	3	0.7401
CmeR	Q7B8P6	Q7B8P6_CAMJU	Campylobacter jejuni	2	0.7385
Cyclin-dependent kinase 2	P24941	CDK2_HUMAN	Homo sapiens	3	0.7359
Biflaviolin synthase CYP158A2	Q9FCA6	C1582_STRCO	Streptomyces coelicolor / M145)	3	0.7358
Tyrosine-protein kinase JAK2	O60674	JAK2_HUMAN	Homo sapiens	3	0.7345
Tubulin alpha-1B chain	P81947	TBA1B_BOVIN	Bos taurus	3	0.7337
Aldo-keto reductase family 1 member B1	P15121	ALDR_HUMAN	Homo sapiens	3	0.7335
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	2	0.7326
Methionine aminopeptidase	P0AE18	MAP1_ECOLI	Escherichia coli	3	0.7316
cAMP-dependent protein kinase catalytic subunit alpha	P00517	KAPCA_BOVIN	Bos taurus	3	0.7307
Photosynthetic reaction center cytochrome c subunit	P07173	CYCR_BLAVI	Blastochloris viridis	3	0.7303
Phosphatidylinositol 5-phosphate 4-kinase type-2 beta	P78356	PI42B_HUMAN	Homo sapiens	3	0.7286
Catechol O-methyltransferase	P22734	COMT_RAT	Rattus norvegicus	3	0.7279
Peripheral plasma membrane protein CASK	O14936	CSKP_HUMAN	Homo sapiens	3	0.7275
Casein kinase II subunit alpha	P68400	CSK21_HUMAN	Homo sapiens	3	0.7273
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.7265
Cyclin-dependent kinase 2	P24941	CDK2_HUMAN	Homo sapiens	3	0.7246
Focal adhesion kinase 1	Q00944	FAK1_CHICK	Gallus gallus	3	0.7244
Fatty acid-binding protein, intestinal	P12104	FABPI_HUMAN	Homo sapiens	3	0.7220
Prostaglandin G/H synthase 1	P05979	PGH1_SHEEP	Ovis aries	3	0.7217
S-adenosylmethionine decarboxylase proenzyme	P17707	DCAM_HUMAN	Homo sapiens	3	0.7211
Mitochondrial poly(A) polymerase	F1NBW0	F1NBW0_CHICK	Gallus gallus	2	0.7194
Genome polyprotein	O92972	POLG_HCVJ4	Hepatitis C virus genotype 1b	3	0.7181
Cyclin-dependent kinase 2	P24941	CDK2_HUMAN	Homo sapiens	3	0.7177
Beta-2 adrenergic receptor	P07550	ADRB2_HUMAN	Homo sapiens	3	0.7174
Focal adhesion kinase 1	Q00944	FAK1_CHICK	Gallus gallus	3	0.7172
Pteridine reductase, putative	Q581W1	Q581W1_TRYB2	Trypanosoma brucei brucei	3	0.7157
Sepiapterin reductase	Q64105	SPRE_MOUSE	Mus musculus	3	0.7144
Glucan 1,3-beta-glucosidase	P29717	EXG1_CANAL	Candida albicans	2	0.7144
Ribosyldihydronicotinamide dehydrogenase [quinone]	P16083	NQO2_HUMAN	Homo sapiens	3	0.7141
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	4	0.7137
Aurora kinase A	O14965	AURKA_HUMAN	Homo sapiens	3	0.7124
Cyclin-dependent kinase 9	P50750	CDK9_HUMAN	Homo sapiens	3	0.7107
Focal adhesion kinase 1	Q00944	FAK1_CHICK	Gallus gallus	3	0.7103
Beta-1 adrenergic receptor	P07700	ADRB1_MELGA	Meleagris gallopavo	3	0.7100
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A	O76083	PDE9A_HUMAN	Homo sapiens	3	0.7089
Casein kinase II subunit alpha	P68400	CSK21_HUMAN	Homo sapiens	3	0.7087
Pteridine reductase 1	Q01782	PTR1_LEIMA	Leishmania major	2	0.7078
Deoxyribodipyrimidine photo-lyase	Q8PYK9	Q8PYK9_METMA	Methanosarcina mazei	4	0.7068
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	4	0.7068
Mycinamicin III 3''-O-methyltransferase	Q49492	MYCF_MICGR	Micromonospora griseorubida	2	0.7068
Genome polyprotein	P26663	POLG_HCVBK	Hepatitis C virus genotype 1b	4	0.7064
Dihydrofolate reductase	P00374	DYR_HUMAN	Homo sapiens	3	0.7051
SRSF protein kinase 1	Q96SB4	SRPK1_HUMAN	Homo sapiens	3	0.7045
GTPase IMAP family member 2	Q9UG22	GIMA2_HUMAN	Homo sapiens	3	0.7045
ActVA 6 protein	Q53908	Q53908_STRCH	Streptomyces coelicolor	3	0.7042
Precorrin-3 methylase	O68097	O68097_RHOCA	Rhodobacter capsulatus	3	0.7039
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	3	0.7026

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