ANPDB

Select a section from the left sidebar

Iso-gamma-fagarine

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

Canonical Smiles	COc1cccc2c1n(C)c1c(c2=O)cco1
InChI	InChI=1S/C13H11NO3/c1-14-11-8(4-3-5-10(11)16-2)12(15)9-6-7-17-13(9)14/h3-7H,1-2H3
InChIKey	VNBUMBNLPGLBML-UHFFFAOYSA-N
Formula	C₁₃H₁₁NO₃
HBA	4
HBD	0
MW	229.23
Rotatable Bonds	1
TPSA	44.37
LogP	2.29
Number Rings	3
Number Aromatic Rings	3
Heavy Atom Count	17
Formal Charge	0
Fraction CSP3	0.15
Exact Mass	229.07
Number of Lipinski Rule Violations	0

#	Species	Family	Kingdom	NCBI Taxonomy ID
1	Fagara heitzii	Rutaceae	Plantae	—

Showing of synonyms

Mbaze LM, Lado JA, et al. (2009). Oxidative burst inhibitory and cytotoxic amides and lignans from the stem bark of Fagara heitzii (Rutaceae).. Phytochemistry,2009, 70(11-12), 1442-1447. [View] [PubMed]

Pubchem: 927945

Cas: 569-02-8

Zinc: ZINC000000517887

Nmrshiftdb2: 60075023

Chembl: CHEMBL447997

No compound-protein relationship available.

SMILES: c1coc(c12)[nH]c3c(c2=O)cccc3

Level: 0

Mol. Weight: 229.23 g/mol

Suppressive on phagocytosis response upon activation with serum

Absorption

Caco-2 (logPapp): -4.59
Human Oral Bioavailability 20%: Bioavailable
Human Intestinal Absorption: Absorbed
Madin-Darby Canine Kidney: -4.040
Human Oral Bioavailability 50%: Bioavailable
P-Glycoprotein Inhibitor: Non-Inhibitor
P-Glycoprotein Substrate: Non-Substrate
Skin Permeability: -2.04

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Penetrable
Fraction Unbound (Human): 1.060
Plasma Protein Binding: 67.26
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: Non-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: 11.100
Organic Cation Transporter 2: Non-Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Toxic
Avian: Safe
Bee: Safe
Bioconcentration Factor: 1.140
Biodegradation: Safe
Carcinogenesis: Toxic
Crustacean: Toxic
Liver Injury I (DILI): Safe
Eye Corrosion: Safe
Eye Irritation: Safe
Maximum Tolerated Dose: -0.460
Liver Injury II: Toxic
hERG Blockers: Safe
Daphnia Maga: 4.080
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: 3.690
Rat (Acute): 2.500
Rat (Chronic Oral): 2.200
Fathead Minnow: 4.570
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: 389.070
Hydration Free Energy: -11.860
Log(D) at pH=7.4: 2.120
Log(P): 2.44
Log S: -3.22
Log(Vapor Pressure): -6.05
Melting Point: 163.3
pKa Acid: 6.95
pKa Basic: 5.25

Protein Name	UniProt ID	Entry Name	Species	#Pharmacophore Points	Probability (0.7 ≤ Tversky Score ≤ 1.0)
Methionine aminopeptidase	P0AE18	MAP1_ECOLI	Escherichia coli	3	0.9502
Alpha-ketoglutarate-dependent dioxygenase FTO	Q9C0B1	FTO_HUMAN	Homo sapiens	3	0.9406
Fatty acid-binding protein, intestinal	P12104	FABPI_HUMAN	Homo sapiens	3	0.9334
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.9318
Methionine aminopeptidase 2	P9WK19	MAP12_MYCTU	Mycobacterium tuberculosis	3	0.9256
Glycylpeptide N-tetradecanoyltransferase	Q4Q5S8	Q4Q5S8_LEIMA	Leishmania major	3	0.9094
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.9024
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	4	0.9010
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase	Q9TQS6	DHDH_MACFA	Macaca fascicularis	3	0.8981
Methionine aminopeptidase	P0AE18	MAP1_ECOLI	Escherichia coli	3	0.8941
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.8935
Succinate dehydrogenase flavoprotein subunit	P0AC41	SDHA_ECOLI	Escherichia coli	3	0.8869
Prostaglandin G/H synthase 2	Q05769	PGH2_MOUSE	Mus musculus	3	0.8644
Mitogen-activated protein kinase 10	P53779	MK10_HUMAN	Homo sapiens	3	0.8643
Sex hormone-binding globulin	P04278	SHBG_HUMAN	Homo sapiens	3	0.8580
Mycinamicin III 3''-O-methyltransferase	Q49492	MYCF_MICGR	Micromonospora griseorubida	2	0.8512
Sex hormone-binding globulin	P04278	SHBG_HUMAN	Homo sapiens	3	0.8497
Serine/threonine-protein kinase pim-1	P11309	PIM1_HUMAN	Homo sapiens	3	0.8473
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.8453
Biflaviolin synthase CYP158A1	Q9KZF5	C1581_STRCO	Streptomyces coelicolor / M145)	3	0.8424
Proto-oncogene tyrosine-protein kinase Src	P12931	SRC_HUMAN	Homo sapiens	3	0.8419
Soluble acetylcholine receptor	Q8WSF8	Q8WSF8_APLCA	Aplysia californica	3	0.8366
HTH-type transcriptional regulator QacR	P0A0N4	QACR_STAAU	Staphylococcus aureus	3	0.8349
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.8259
Enoyl-ACP reductase	Q9BJJ9	Q9BJJ9_PLAFA	Plasmodium falciparum	3	0.8245
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	3	0.8225
Casein kinase II subunit alpha	P28523	CSK2A_MAIZE	Zea mays	3	0.8220
Biphenyl dioxygenase subunit alpha	P37333	BPHA_PARXL	Paraburkholderia xenovorans	3	0.8196
Activin receptor type-1	Q04771	ACVR1_HUMAN	Homo sapiens	3	0.8149
Toxoflavin degrading enzyme	E3SET7	E3SET7_PAEPO	Paenibacillus polymyxa	3	0.8148
Steroid Delta-isomerase	P07445	SDIS_PSEPU	Pseudomonas putida	2	0.8146
Casein kinase II subunit alpha	P28523	CSK2A_MAIZE	Zea mays	3	0.8141
Methionine aminopeptidase	P0AE18	MAP1_ECOLI	Escherichia coli	3	0.8121
Proto-oncogene tyrosine-protein kinase Src	P12931	SRC_HUMAN	Homo sapiens	3	0.8121
Casein kinase II subunit alpha	P28523	CSK2A_MAIZE	Zea mays	3	0.8119
Riboflavin synthase	P0AFU8	RISA_ECOLI	Escherichia coli	3	0.8092
Casein kinase II subunit alpha	P28523	CSK2A_MAIZE	Zea mays	3	0.8009
Albumin	P02768	ALBU_HUMAN	Homo sapiens	3	0.8008
Ribosyldihydronicotinamide dehydrogenase [quinone]	P16083	NQO2_HUMAN	Homo sapiens	3	0.8005
Lactoylglutathione lyase	Q9CPU0	LGUL_MOUSE	Mus musculus	2	0.8002
Odorant-binding protein	P81245	OBP_PIG	Sus scrofa	3	0.7975
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.7962
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.7956
Methionine aminopeptidase	P0AE18	MAP1_ECOLI	Escherichia coli	3	0.7945
Trichothecene 15-O-acetyltransferase TRI3	Q9C1B7	TRI3_FUSSP	Fusarium sporotrichioides	3	0.7855
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	2	0.7851
Bromodomain-containing protein 4	O60885	BRD4_HUMAN	Homo sapiens	3	0.7844
Cyclin-dependent kinase 2	P24941	CDK2_HUMAN	Homo sapiens	3	0.7838
Gag-Pol polyprotein	P03366	POL_HV1B1	Human immunodeficiency virus type 1 group M subtype B	3	0.7837
Aldo-keto reductase family 1 member B1	P15121	ALDR_HUMAN	Homo sapiens	3	0.7828
Steroid Delta-isomerase	P07445	SDIS_PSEPU	Pseudomonas putida	3	0.7824
Serine/threonine-protein kinase Chk1	O14757	CHK1_HUMAN	Homo sapiens	3	0.7815
ActVA 6 protein	Q53908	Q53908_STRCH	Streptomyces coelicolor	3	0.7809
Peptidyl-prolyl cis-trans isomerase FKBP1A	P62942	FKB1A_HUMAN	Homo sapiens	3	0.7798
Aldo-keto reductase family 1 member C2	P52895	AK1C2_HUMAN	Homo sapiens	2	0.7732
Alcohol dehydrogenase E chain	P00327	ADH1E_HORSE	Equus caballus	3	0.7722
Aldo-keto reductase family 1 member B10	O60218	AK1BA_HUMAN	Homo sapiens	3	0.7695
Aldo-keto reductase family 1 member B1	P15121	ALDR_HUMAN	Homo sapiens	3	0.7687
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	2	0.7666
Bromodomain-containing protein 4	O60885	BRD4_HUMAN	Homo sapiens	3	0.7661
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform	P48736	PK3CG_HUMAN	Homo sapiens	3	0.7659
Aldo-keto reductase family 1 member C2	P52895	AK1C2_HUMAN	Homo sapiens	3	0.7639
Acetylcholinesterase	P22303	ACES_HUMAN	Homo sapiens	3	0.7627
Thymidylate synthase	P00469	TYSY_LACCA	Lacticaseibacillus casei	2	0.7616
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	3	0.7597
Serine/threonine-protein kinase 24	Q9Y6E0	STK24_HUMAN	Homo sapiens	3	0.7590
Dipeptidyl peptidase 4	P27487	DPP4_HUMAN	Homo sapiens	3	0.7588
Aldo-keto reductase family 1 member C2	P52895	AK1C2_HUMAN	Homo sapiens	3	0.7584
3-phosphoinositide-dependent protein kinase 1	O15530	PDPK1_HUMAN	Homo sapiens	3	0.7583
Angiotensin-converting enzyme 2	Q9BYF1	ACE2_HUMAN	Homo sapiens	2	0.7576
Casein kinase II subunit alpha	P68400	CSK21_HUMAN	Homo sapiens	3	0.7568
Peptidyl-prolyl cis-trans isomerase FKBP5	Q13451	FKBP5_HUMAN	Homo sapiens	3	0.7553
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.7552
Peroxisome proliferator-activated receptor gamma	P37231	PPARG_HUMAN	Homo sapiens	2	0.7531
Aklavinone 12-hydroxylase RdmE	Q54530	DNRF_STREF	Streptomyces purpurascens	4	0.7529
Acetylcholinesterase	P04058	ACES_TETCF	Tetronarce californica	3	0.7524
Chitinase A	Q9AMP1	Q9AMP1_VIBHA	Vibrio harveyi	2	0.7498
Steroid Delta-isomerase	P07445	SDIS_PSEPU	Pseudomonas putida	2	0.7489
Death-associated protein kinase 1	P53355	DAPK1_HUMAN	Homo sapiens	3	0.7485
Caspase-7	P55210	CASP7_HUMAN	Homo sapiens	3	0.7467
Peptidyl-prolyl cis-trans isomerase FKBP1A	P62942	FKB1A_HUMAN	Homo sapiens	2	0.7465
Bromodomain-containing protein 2	P25440	BRD2_HUMAN	Homo sapiens	3	0.7462
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	2	0.7459
NAD(P)H dehydrogenase [quinone] 1	P15559	NQO1_HUMAN	Homo sapiens	3	0.7458
Serine/threonine-protein kinase Chk1	O14757	CHK1_HUMAN	Homo sapiens	3	0.7445
Chloramphenicol acetyltransferase	P62577	CAT_ECOLX	Escherichia coli	2	0.7436
Tyrosine-protein kinase Lck	P06239	LCK_HUMAN	Homo sapiens	3	0.7423
Deoxynucleoside kinase	Q9XZT6	DNK_DROME	Drosophila melanogaster	5	0.7404
Bromodomain-containing protein 4	O60885	BRD4_HUMAN	Homo sapiens	3	0.7393
Aldo-keto reductase family 1 member C2	P52895	AK1C2_HUMAN	Homo sapiens	2	0.7384
3-ketosteroid dehydrogenase	Q9RA02	Q9RA02_RHOER	Rhodococcus erythropolis	2	0.7375
Biflaviolin synthase CYP158A2	Q9FCA6	C1582_STRCO	Streptomyces coelicolor / M145)	3	0.7366
Fatty acid-binding protein, adipocyte	P15090	FABP4_HUMAN	Homo sapiens	2	0.7364
Aldo-keto reductase family 1 member C2	P52895	AK1C2_HUMAN	Homo sapiens	3	0.7357
Casein kinase II subunit alpha	P68400	CSK21_HUMAN	Homo sapiens	3	0.7343
Steroid Delta-isomerase	P07445	SDIS_PSEPU	Pseudomonas putida	3	0.7340
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	2	0.7338
Casein kinase II subunit alpha	P28523	CSK2A_MAIZE	Zea mays	3	0.7333
Sex hormone-binding globulin	P04278	SHBG_HUMAN	Homo sapiens	3	0.7326
Bromodomain testis-specific protein	Q58F21	BRDT_HUMAN	Homo sapiens	3	0.7299
Retinoic acid receptor RXR-alpha	P19793	RXRA_HUMAN	Homo sapiens	2	0.7290
Serine/threonine-protein kinase 24	Q9Y6E0	STK24_HUMAN	Homo sapiens	3	0.7287
Cyclin-dependent kinase 2	P24941	CDK2_HUMAN	Homo sapiens	3	0.7286
3-phosphoinositide-dependent protein kinase 1	O15530	PDPK1_HUMAN	Homo sapiens	3	0.7285
Genome polyprotein	O92972	POLG_HCVJ4	Hepatitis C virus genotype 1b	3	0.7267
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	2	0.7265
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	2	0.7257
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.7253
Adenosine kinase	P55263	ADK_HUMAN	Homo sapiens	3	0.7249
Gastrotropin	Q6IMW5	Q6IMW5_DANRE	Danio rerio	2	0.7249
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	3	0.7247
Protoporphyrinogen oxidase, mitochondrial	O24164	PPOM_TOBAC	Nicotiana tabacum	2	0.7244
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	2	0.7237
Gag-Pol polyprotein	P03366	POL_HV1B1	Human immunodeficiency virus type 1 group M subtype B	3	0.7203
Abscisic acid receptor PYL10	Q8H1R0	PYL10_ARATH	Arabidopsis thaliana	3	0.7203
11-beta-hydroxysteroid dehydrogenase 1	P28845	DHI1_HUMAN	Homo sapiens	3	0.7190
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	2	0.7190
Bromodomain-containing protein 4	O60885	BRD4_HUMAN	Homo sapiens	3	0.7188
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.7186
Abscisic acid receptor PYL1	Q8VZS8	PYL1_ARATH	Arabidopsis thaliana	2	0.7184
Carminomycin 4-O-methyltransferase DnrK	Q06528	DNRK_STRPE	Streptomyces peucetius	2	0.7170
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	2	0.7166
Bromodomain-containing protein 4	O60885	BRD4_HUMAN	Homo sapiens	3	0.7162
ADP compounds hydrolase NudE	P45799	NUDE_ECOLI	Escherichia coli	2	0.7156
Prostaglandin F2a synthase	Q8I6L9	Q8I6L9_TRYCR	Trypanosoma cruzi	2	0.7150
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.7149
Capsid protein	Q9WBP8	Q9WBP8_9VIRU	Adeno-associated virus - 1	2	0.7148
Agglutinin alpha chain	P18674	LECA_MACPO	Maclura pomifera	3	0.7147
F420-dependent methylenetetrahydromethanopterin dehydrogenase	P94951	MTD_METKA	Methanopyrus kandleri	2	0.7138
Cyclin-dependent kinase 2	P24941	CDK2_HUMAN	Homo sapiens	3	0.7130
Methionine aminopeptidase	P0AE18	MAP1_ECOLI	Escherichia coli	2	0.7126
Prostaglandin G/H synthase 1	P05979	PGH1_SHEEP	Ovis aries	3	0.7115
Ceramide transfer protein	Q9Y5P4	CERT_HUMAN	Homo sapiens	3	0.7114
Prostaglandin G/H synthase 1	P05979	PGH1_SHEEP	Ovis aries	3	0.7110
Abscisic acid receptor PYL3	Q9SSM7	PYL3_ARATH	Arabidopsis thaliana	2	0.7096
Prostaglandin G/H synthase 2	Q05769	PGH2_MOUSE	Mus musculus	3	0.7095
Alcohol dehydrogenase E chain	P00327	ADH1E_HORSE	Equus caballus	3	0.7091
Serine/threonine-protein kinase pim-1	P11309	PIM1_HUMAN	Homo sapiens	3	0.7088
Casein kinase I isoform gamma-3	Q9Y6M4	KC1G3_HUMAN	Homo sapiens	3	0.7086
Alcohol dehydrogenase E chain	P00327	ADH1E_HORSE	Equus caballus	3	0.7078
Bromodomain-containing protein 4	O60885	BRD4_HUMAN	Homo sapiens	3	0.7077
Nucleoprotein	P33469	NCAP_CVHOC	Human coronavirus OC43	3	0.7067
D-alanyl-D-alanine carboxypeptidase	P15555	DAC_STRSR	Streptomyces sp	2	0.7067
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A	Q9Y233	PDE10_HUMAN	Homo sapiens	3	0.7063
Aldo-keto reductase family 1 member B1	P80276	ALDR_PIG	Sus scrofa	4	0.7057
Poly [ADP-ribose] polymerase tankyrase-2	Q9H2K2	TNKS2_HUMAN	Homo sapiens	3	0.7056
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	2	0.7056
Jasmonoyl--L-amino acid synthetase JAR1	Q9SKE2	JAR1_ARATH	Arabidopsis thaliana	3	0.7055
Steroid Delta-isomerase	P07445	SDIS_PSEPU	Pseudomonas putida	2	0.7055
Cytochrome P450 2C5	P00179	CP2C5_RABIT	Oryctolagus cuniculus	2	0.7044
Lactotransferrin	P24627	TRFL_BOVIN	Bos taurus	2	0.7040
Biflaviolin synthase CYP158A2	Q9FCA6	C1582_STRCO	Streptomyces coelicolor / M145)	3	0.7037
Thymidylate synthase	P0A886	TYSY_ECO57	Escherichia coli O157:H7	2	0.7032
Estrogen receptor	P03372	ESR1_HUMAN	Homo sapiens	2	0.7019
Exotoxin A	P11439	TOXA_PSEAE	Pseudomonas aeruginosa	3	0.7016
Mycocyclosin synthase	P9WPP7	CP121_MYCTU	Mycobacterium tuberculosis	2	0.7012
Aldo-keto reductase family 1 member B1	P80276	ALDR_PIG	Sus scrofa	3	0.7007
Pheromone-binding protein ASP1	Q9U9J6	Q9U9J6_APIME	Apis mellifera	2	0.7006

Download SDF