ANPDB

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Kokusaginine B

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

Canonical Smiles	COc1cc2nc(OC)c3c(c2cc1OC)occ3
InChI	InChI=1S/C14H13NO4/c1-16-11-6-9-10(7-12(11)17-2)15-14(18-3)8-4-5-19-13(8)9/h4-7H,1-3H3
InChIKey	YENFCXOMLBXHTB-UHFFFAOYSA-N
Formula	C₁₄H₁₃NO₄
HBA	5
HBD	0
MW	259.26
Rotatable Bonds	3
TPSA	53.72
LogP	3.01
Number Rings	3
Number Aromatic Rings	3
Heavy Atom Count	19
Formal Charge	0
Fraction CSP3	0.21
Exact Mass	259.08
Number of Lipinski Rule Violations	0

#	Species	Family	Kingdom	NCBI Taxonomy ID
1	Araliopsis soyauxii	Rutaceae	Plantae	1317904

Showing of synonyms

Nganou BK, Mbaveng AT, et al. (2019). Furoquinolines and dihydrooxazole alkaloids with cytotoxic activity from the stem bark of Araliopsis soyauxii.. Fitoterapia,2019, 133, 193-199. [View] [PubMed]

No compound-protein relationship available.

SMILES: c1coc(c12)c3c(nc2)cccc3

Level: 0

Mol. Weight: 259.26 g/mol

Cytotoxic

Absorption

Caco-2 (logPapp): -4.55
Human Oral Bioavailability 20%: Bioavailable
Human Intestinal Absorption: Absorbed
Madin-Darby Canine Kidney: -4.220
Human Oral Bioavailability 50%: Non-Bioavailable
P-Glycoprotein Inhibitor: Non-Inhibitor
P-Glycoprotein Substrate: Non-Substrate
Skin Permeability: -2.38

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Penetrable
Fraction Unbound (Human): 0.810
Plasma Protein Binding: 57.51
Steady State Volume of Distribution: -

Metabolism

Breast Cancer Resistance Protein: Inhibitor
CYP 1A2 Inhibitor: Inhibitor
CYP 1A2 Substrate: Substrate
CYP 2C19 Inhibitor: Non-Inhibitor
CYP 2C19 Substrate: Non-Substrate
CYP 2C9 Inhibitor: Non-Inhibitor
CYP 2C9 Substrate: Non-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: 7.100
Organic Cation Transporter 2: Non-Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Toxic
Avian: Safe
Bee: Safe
Bioconcentration Factor: 2.000
Biodegradation: Safe
Carcinogenesis: Toxic
Crustacean: Toxic
Liver Injury I (DILI): Toxic
Eye Corrosion: Safe
Eye Irritation: Toxic
Maximum Tolerated Dose: 1.430
Liver Injury II: Toxic
hERG Blockers: Safe
Daphnia Maga: 5.110
Micronucleos: Toxic
NR-AhR: Safe
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: 3.310
Rat (Acute): 2.210
Rat (Chronic Oral): 2.040
Fathead Minnow: 4.940
Respiratory Disease: Toxic
Skin Sensitisation: Safe
SR-ARE: Safe
SR-ATAD5: Safe
SR-HSE: Safe
SR-MMP: Safe
SR-p53: Safe

General Properties

Boiling Point: 388.090
Hydration Free Energy: -9.760
Log(D) at pH=7.4: 2.840
Log(P): 2.96
Log S: -2.95
Log(Vapor Pressure): -5.26
Melting Point: 139.54
pKa Acid: 5.95
pKa Basic: 5.86

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	0.9665
2,7-dihydroxy-5-methyl-1-naphthoate 7-O-methyltransferase	Q84HC8	NCSB1_STRCZ	Streptomyces carzinostaticus	3	0.9602
Glycogen phosphorylase, muscle form	P00489	PYGM_RABIT	Oryctolagus cuniculus	3	0.9456
Bromodomain-containing protein 2	P25440	BRD2_HUMAN	Homo sapiens	3	0.9447
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.9382
cGMP-specific 3',5'-cyclic phosphodiesterase	O76074	PDE5A_HUMAN	Homo sapiens	3	0.9347
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.9333
Bromodomain-containing protein 4	O60885	BRD4_HUMAN	Homo sapiens	3	0.9277
Biflaviolin synthase CYP158A1	Q9KZF5	C1581_STRCO	Streptomyces coelicolor / M145)	3	0.9210
Steroid Delta-isomerase	P07445	SDIS_PSEPU	Pseudomonas putida	3	0.9195
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.9175
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase	Q9TQS6	DHDH_MACFA	Macaca fascicularis	3	0.9124
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	3	0.9055
Casein kinase II subunit alpha	P68400	CSK21_HUMAN	Homo sapiens	3	0.9054
Bromodomain adjacent to zinc finger domain protein 2B	Q9UIF8	BAZ2B_HUMAN	Homo sapiens	3	0.8998
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	3	0.8993
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A	Q9Y233	PDE10_HUMAN	Homo sapiens	3	0.8965
Steroid Delta-isomerase	P07445	SDIS_PSEPU	Pseudomonas putida	3	0.8952
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	4	0.8938
Steroid Delta-isomerase	P00947	SDIS_COMTE	Comamonas testosteroni	3	0.8930
Carminomycin 4-O-methyltransferase DnrK	Q06528	DNRK_STRPE	Streptomyces peucetius	3	0.8927
Glycogen synthase kinase-3 beta	P49841	GSK3B_HUMAN	Homo sapiens	3	0.8921
Steroid Delta-isomerase	P07445	SDIS_PSEPU	Pseudomonas putida	3	0.8875
Steroid Delta-isomerase	P07445	SDIS_PSEPU	Pseudomonas putida	3	0.8865
Cytochrome P450 monooxygenase	Q5YNS8	Q5YNS8_NOCFA	Nocardia farcinica	3	0.8792
Cathepsin S	P25774	CATS_HUMAN	Homo sapiens	3	0.8744
Probable esterase KAI2	Q9SZU7	KAI2_ARATH	Arabidopsis thaliana	3	0.8733
Retinoic acid receptor RXR-alpha	P19793	RXRA_HUMAN	Homo sapiens	3	0.8715
2,7-dihydroxy-5-methyl-1-naphthoate 7-O-methyltransferase	Q84HC8	NCSB1_STRCZ	Streptomyces carzinostaticus	3	0.8704
2-phospho-L-lactate transferase	Q8PVT6	COFD_METMA	Methanosarcina mazei	3	0.8643
Acetylcholinesterase	P22303	ACES_HUMAN	Homo sapiens	3	0.8614
Na(+):neurotransmitter symporter (Snf family)	O67854	O67854_AQUAE	Aquifex aeolicus	3	0.8447
Tubulin alpha-1B chain	P81947	TBA1B_BOVIN	Bos taurus	3	0.8440
Sulfotransferase 2A1	Q06520	ST2A1_HUMAN	Homo sapiens	3	0.8437
Photosynthetic reaction center cytochrome c subunit	P07173	CYCR_BLAVI	Blastochloris viridis	3	0.8425
Toxoflavin degrading enzyme	E3SET7	E3SET7_PAEPO	Paenibacillus polymyxa	3	0.8381
Cytochrome P450 2A6	P11509	CP2A6_HUMAN	Homo sapiens	3	0.8321
CREB-binding protein	Q92793	CBP_HUMAN	Homo sapiens	3	0.8306
Aromatase	P11511	CP19A_HUMAN	Homo sapiens	3	0.8289
Photosynthetic reaction center cytochrome c subunit	P07173	CYCR_BLAVI	Blastochloris viridis	3	0.8217
CmeR	Q7B8P6	Q7B8P6_CAMJU	Campylobacter jejuni	3	0.8171
Tubulin alpha chain	D0VWZ0	D0VWZ0_SHEEP	Ovis aries	3	0.8167
Proto-oncogene tyrosine-protein kinase Src	P00523	SRC_CHICK	Gallus gallus	3	0.8089
Enoyl-ACP reductase	Q9BJJ9	Q9BJJ9_PLAFA	Plasmodium falciparum	3	0.8083
Steroid Delta-isomerase	P07445	SDIS_PSEPU	Pseudomonas putida	3	0.8079
Steroid Delta-isomerase	P07445	SDIS_PSEPU	Pseudomonas putida	3	0.8074
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	3	0.8062
Steroid Delta-isomerase	P00947	SDIS_COMTE	Comamonas testosteroni	3	0.8062
Acetylcholine-binding protein	P58154	ACHP_LYMST	Lymnaea stagnalis	3	0.8013
Biphenyl dioxygenase subunit alpha	P37333	BPHA_PARXL	Paraburkholderia xenovorans	3	0.7989
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.7949
NAD(P)H dehydrogenase [quinone] 1	P15559	NQO1_HUMAN	Homo sapiens	3	0.7935
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A	Q9Y233	PDE10_HUMAN	Homo sapiens	3	0.7933
Putative ketoacyl reductase	P16544	ACT3_STRCO	Streptomyces coelicolor / M145)	3	0.7911
Biflaviolin synthase CYP158A2	Q9FCA6	C1582_STRCO	Streptomyces coelicolor / M145)	3	0.7905
Aldo-keto reductase family 1 member B1	P15121	ALDR_HUMAN	Homo sapiens	4	0.7900
Dihydroorotate dehydrogenase (quinone), mitochondrial	Q08210	PYRD_PLAF7	Plasmodium falciparum	3	0.7864
Cis-2,3-dihydrobiphenyl-2,3-diol dehydrogenase	Q46381	BPHB_COMTE	Comamonas testosteroni	3	0.7852
Steroid Delta-isomerase	P07445	SDIS_PSEPU	Pseudomonas putida	2	0.7847
Tyrosine-protein kinase Lck	P06239	LCK_HUMAN	Homo sapiens	3	0.7835
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	3	0.7832
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A	Q9Y233	PDE10_HUMAN	Homo sapiens	3	0.7827
Biflaviolin synthase CYP158A2	Q9FCA6	C1582_STRCO	Streptomyces coelicolor / M145)	3	0.7820
Genome polyprotein	O92972	POLG_HCVJ4	Hepatitis C virus genotype 1b	3	0.7795
Nitroreductase domain-containing protein	Q8DW21	Q8DW21_STRMU	Streptococcus mutans serotype c	3	0.7782
Sulfotransferase 2B1	O00204	ST2B1_HUMAN	Homo sapiens	2	0.7775
Nucleoprotein	P33469	NCAP_CVHOC	Human coronavirus OC43	3	0.7773
3-phosphoinositide-dependent protein kinase 1	O15530	PDPK1_HUMAN	Homo sapiens	3	0.7766
CmeR	Q7B8P6	Q7B8P6_CAMJU	Campylobacter jejuni	2	0.7731
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	3	0.7729
Gag-Pol polyprotein	P04585	POL_HV1H2	Human immunodeficiency virus type 1 group M subtype B	4	0.7720
Serine/threonine-protein kinase Chk1	O14757	CHK1_HUMAN	Homo sapiens	3	0.7708
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	2	0.7694
HTH-type transcriptional regulator EthR	P9WMC1	ETHR_MYCTU	Mycobacterium tuberculosis	3	0.7687
Protein mono-ADP-ribosyltransferase PARP3	Q9Y6F1	PARP3_HUMAN	Homo sapiens	3	0.7685
Poly [ADP-ribose] polymerase tankyrase-2	Q9H2K2	TNKS2_HUMAN	Homo sapiens	3	0.7679
Gag-Pol polyprotein	P04585	POL_HV1H2	Human immunodeficiency virus type 1 group M subtype B	4	0.7670
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.7663
Steroid Delta-isomerase	P00947	SDIS_COMTE	Comamonas testosteroni	2	0.7638
Death-associated protein kinase 1	P53355	DAPK1_HUMAN	Homo sapiens	3	0.7635
Steroid Delta-isomerase	P00947	SDIS_COMTE	Comamonas testosteroni	3	0.7635
Bromodomain-containing protein 2	P25440	BRD2_HUMAN	Homo sapiens	3	0.7630
Lactoylglutathione lyase	Q9CPU0	LGUL_MOUSE	Mus musculus	2	0.7603
Aldo-keto reductase family 1 member C2	P52895	AK1C2_HUMAN	Homo sapiens	3	0.7602
Exotoxin A	P11439	TOXA_PSEAE	Pseudomonas aeruginosa	3	0.7591
Serine/threonine-protein kinase Chk1	O14757	CHK1_HUMAN	Homo sapiens	3	0.7577
Chitinase A	Q9AMP1	Q9AMP1_VIBHA	Vibrio harveyi	2	0.7570
Bromodomain-containing protein 4	O60885	BRD4_HUMAN	Homo sapiens	3	0.7562
3-alpha-hydroxysteroid dehydrogenase	P23457	DIDH_RAT	Rattus norvegicus	3	0.7558
Steroid 21-hydroxylase	P08686	CP21A_HUMAN	Homo sapiens	3	0.7556
Aldo-keto reductase family 1 member C2	P52895	AK1C2_HUMAN	Homo sapiens	2	0.7531
Nuclear receptor ROR-beta	P45446	RORB_RAT	Rattus norvegicus	2	0.7527
Proliferating cell nuclear antigen	P12004	PCNA_HUMAN	Homo sapiens	3	0.7525
Steroid Delta-isomerase	P07445	SDIS_PSEPU	Pseudomonas putida	2	0.7524
Bromodomain-containing protein 4	O60885	BRD4_HUMAN	Homo sapiens	3	0.7520
Catalase-peroxidase 2	O59651	KATG2_HALMA	Haloarcula marismortui	2	0.7506
Lactotransferrin	P24627	TRFL_BOVIN	Bos taurus	2	0.7503
Casein kinase II subunit alpha	P68400	CSK21_HUMAN	Homo sapiens	3	0.7501
Fatty acid-binding protein, intestinal	P12104	FABPI_HUMAN	Homo sapiens	3	0.7489
Aromatase	P11511	CP19A_HUMAN	Homo sapiens	3	0.7485
Serine/threonine-protein kinase 24	Q9Y6E0	STK24_HUMAN	Homo sapiens	3	0.7472
Gag-Pol polyprotein	P04585	POL_HV1H2	Human immunodeficiency virus type 1 group M subtype B	4	0.7450
Lethal(3)malignant brain tumor-like protein 1	Q9Y468	LMBL1_HUMAN	Homo sapiens	3	0.7423
Cyclin-dependent kinase 2	P24941	CDK2_HUMAN	Homo sapiens	2	0.7419
ADP-ribosylation factor 1	P84080	ARF1_BOVIN	Bos taurus	3	0.7399
Tyrosine-protein kinase Lck	P06239	LCK_HUMAN	Homo sapiens	3	0.7393
Steroid Delta-isomerase	P00947	SDIS_COMTE	Comamonas testosteroni	2	0.7391
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase	Q05603	COBT_SALTY	Salmonella typhimurium	2	0.7385
Cytochrome P450 2A6	P11509	CP2A6_HUMAN	Homo sapiens	3	0.7378
Agglutinin alpha chain	P18674	LECA_MACPO	Maclura pomifera	3	0.7376
Uncharacterized protein	Q3F0V8	Q3F0V8_BACTI	Bacillus thuringiensis serovar israelensis ATCC 35646	3	0.7353
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	2	0.7350
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.7344
Poly [ADP-ribose] polymerase tankyrase-2	Q9H2K2	TNKS2_HUMAN	Homo sapiens	3	0.7336
TDP-4-oxo-6-deoxy-alpha-D-glucose-3,4-oxoisomerase	Q6T1W8	FDTA_ANETH	Aneurinibacillus thermoaerophilus	3	0.7332
Acetylcholinesterase	P21836	ACES_MOUSE	Mus musculus	2	0.7322
Gastrotropin	Q6IMW5	Q6IMW5_DANRE	Danio rerio	2	0.7320
Acetylcholinesterase	P04058	ACES_TETCF	Tetronarce californica	3	0.7316
Poly [ADP-ribose] polymerase tankyrase-2	Q9H2K2	TNKS2_HUMAN	Homo sapiens	3	0.7314
17-beta-hydroxysteroid dehydrogenase type 1	P14061	DHB1_HUMAN	Homo sapiens	2	0.7296
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	2	0.7293
Methionine aminopeptidase	P0AE18	MAP1_ECOLI	Escherichia coli	2	0.7286
AGAP003309-PA	A0A1U7F4W2	A0A1U7F4W2_ANOGA	Anopheles gambiae	3	0.7285
Polymerase acidic protein	C3W5S0	C3W5S0_I09A0	Influenza A virus	2	0.7281
Genome polyprotein	P26663	POLG_HCVBK	Hepatitis C virus genotype 1b	3	0.7279
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	3	0.7278
Renin	P00797	RENI_HUMAN	Homo sapiens	2	0.7266
Retinol dehydratase	Q26490	Q26490_SPOFR	Spodoptera frugiperda	3	0.7253
Acetylcholinesterase	P04058	ACES_TETCF	Tetronarce californica	3	0.7219
Flavoredoxin	Q72HI0	Q72HI0_THET2	Thermus thermophilus	2	0.7211
Serine/threonine-protein kinase pim-1	P11309	PIM1_HUMAN	Homo sapiens	3	0.7207
Prostaglandin reductase 2	Q8N8N7	PTGR2_HUMAN	Homo sapiens	2	0.7189
Cytidine and deoxycytidylate deaminase zinc-binding region	Q82Y41	Q82Y41_NITEU	Nitrosomonas europaea	3	0.7177
Cytochrome P450 monooxygenase	Q5YNS8	Q5YNS8_NOCFA	Nocardia farcinica	3	0.7168
Casein kinase II subunit alpha	P28523	CSK2A_MAIZE	Zea mays	3	0.7166
Steroid Delta-isomerase	P00947	SDIS_COMTE	Comamonas testosteroni	3	0.7160
Serine/threonine-protein kinase Chk1	O14757	CHK1_HUMAN	Homo sapiens	3	0.7159
Poly [ADP-ribose] polymerase tankyrase-2	Q9H2K2	TNKS2_HUMAN	Homo sapiens	3	0.7153
Cholinesterase	P06276	CHLE_HUMAN	Homo sapiens	2	0.7153
Cholesterol oxidase	P22637	CHOD_BREST	Brevibacterium sterolicum	3	0.7146
Aldo-keto reductase family 1 member B1	P15121	ALDR_HUMAN	Homo sapiens	4	0.7136
Peptidyl-prolyl cis-trans isomerase FKBP1A	P62942	FKB1A_HUMAN	Homo sapiens	2	0.7133
Cis-2,3-dihydrobiphenyl-2,3-diol dehydrogenase	Q46381	BPHB_COMTE	Comamonas testosteroni	3	0.7128
Phytohormone-binding protein	G7J032	PHBP_MEDTR	Medicago truncatula	4	0.7101
Bifunctional epoxide hydrolase 2	P34913	HYES_HUMAN	Homo sapiens	2	0.7097
Single-stranded-DNA-specific exonuclease RecJ	D0EM60	D0EM60_DEIRD	Deinococcus radiodurans	2	0.7088
Rhodopsin	P02699	OPSD_BOVIN	Bos taurus	2	0.7074
Sex hormone-binding globulin	P04278	SHBG_HUMAN	Homo sapiens	3	0.7073
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A	Q9Y233	PDE10_HUMAN	Homo sapiens	3	0.7044
Serine/threonine-protein kinase pim-1	P11309	PIM1_HUMAN	Homo sapiens	3	0.7043
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform	P48736	PK3CG_HUMAN	Homo sapiens	3	0.7043
Lactoylglutathione lyase	Q04760	LGUL_HUMAN	Homo sapiens	2	0.7042
Beta-galactoside-specific lectin 4	Q6ITZ3	ML4_VISAL	Viscum album	2	0.7041
Kynurenine/alpha-aminoadipate aminotransferase, mitochondrial	Q8N5Z0	AADAT_HUMAN	Homo sapiens	2	0.7041
Ribosomal small subunit pseudouridine synthase A	P0AA43	RSUA_ECOLI	Escherichia coli	3	0.7037
Adenosine kinase	Q9TVW2	ADK_TOXGO	Toxoplasma gondii	3	0.7036
Bromodomain-containing protein 4	O60885	BRD4_HUMAN	Homo sapiens	3	0.7030
Protoporphyrinogen oxidase	P50336	PPOX_HUMAN	Homo sapiens	3	0.7022
Sulfotransferase 2A1	Q06520	ST2A1_HUMAN	Homo sapiens	3	0.7015
Tryptophan synthase alpha chain	P00929	TRPA_SALTY	Salmonella typhimurium	3	0.7011
cGMP-dependent 3',5'-cyclic phosphodiesterase	O00408	PDE2A_HUMAN	Homo sapiens	2	0.7008

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