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Iso-skimmianine

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

Canonical Smiles	COc1c(OC)ccc2c1n(C)c1c(c2=O)cco1
InChI	InChI=1S/C14H13NO4/c1-15-11-8(4-5-10(17-2)13(11)18-3)12(16)9-6-7-19-14(9)15/h4-7H,1-3H3
InChIKey	LPUGGFROWXFRHP-UHFFFAOYSA-N
Formula	C₁₄H₁₃NO₄
HBA	5
HBD	0
MW	259.26
Rotatable Bonds	2
TPSA	53.6
LogP	2.3
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	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: 621199

Cas: 436-14-6

Zinc: ZINC000000517934

Nmrshiftdb2: 60075742

No compound-protein relationship available.

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

Level: 0

Mol. Weight: 259.26 g/mol

Suppressive on phagocytosis response upon activation with serum

Absorption

Caco-2 (logPapp): -4.52
Human Oral Bioavailability 20%: Bioavailable
Human Intestinal Absorption: Absorbed
Madin-Darby Canine Kidney: -4.180
Human Oral Bioavailability 50%: Bioavailable
P-Glycoprotein Inhibitor: Non-Inhibitor
P-Glycoprotein Substrate: Non-Substrate
Skin Permeability: -1.85

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Penetrable
Fraction Unbound (Human): 1.100
Plasma Protein Binding: 75.44
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: Inhibitor
CYP 2D6 Substrate: Non-Substrate
CYP 3A4 Inhibitor: Inhibitor
CYP 3A4 Substrate: Non-Substrate
OATP1B1: Non-Inhibitor
OATP1B3: Non-Inhibitor

Excretion

Clearance: 10.800
Organic Cation Transporter 2: Non-Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Toxic
Avian: Safe
Bee: Toxic
Bioconcentration Factor: 1.420
Biodegradation: Safe
Carcinogenesis: Toxic
Crustacean: Toxic
Liver Injury I (DILI): Safe
Eye Corrosion: Safe
Eye Irritation: Safe
Maximum Tolerated Dose: -0.290
Liver Injury II: Toxic
hERG Blockers: Safe
Daphnia Maga: 4.810
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: 3.520
Rat (Acute): 2.720
Rat (Chronic Oral): 2.110
Fathead Minnow: 4.740
Respiratory Disease: Safe
Skin Sensitisation: Safe
SR-ARE: Safe
SR-ATAD5: Safe
SR-HSE: Safe
SR-MMP: Safe
SR-p53: Safe

General Properties

Boiling Point: 408.190
Hydration Free Energy: -11.710
Log(D) at pH=7.4: 2.040
Log(P): 1.98
Log S: -3.27
Log(Vapor Pressure): -6.19
Melting Point: 173.7
pKa Acid: 7.16
pKa Basic: 4.93

Protein Name	UniProt ID	Entry Name	Species	#Pharmacophore Points	Probability (0.7 ≤ Tversky Score ≤ 1.0)
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.9492
Alpha-ketoglutarate-dependent dioxygenase FTO	Q9C0B1	FTO_HUMAN	Homo sapiens	3	0.9384
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.9333
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.9282
Methionine aminopeptidase 2	P9WK19	MAP12_MYCTU	Mycobacterium tuberculosis	3	0.9226
Methionine aminopeptidase	P0AE18	MAP1_ECOLI	Escherichia coli	3	0.9132
Fatty acid-binding protein, intestinal	P12104	FABPI_HUMAN	Homo sapiens	3	0.9064
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.9051
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.9029
Tetracycline repressor protein class H	P51561	TETR8_PASMD	Pasteurella multocida	3	0.8946
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	4	0.8930
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.8898
Casein kinase II subunit alpha	P28523	CSK2A_MAIZE	Zea mays	3	0.8847
Tubulin alpha-1B chain	P81947	TBA1B_BOVIN	Bos taurus	3	0.8838
Cyclin-dependent kinase 2	P24941	CDK2_HUMAN	Homo sapiens	3	0.8831
Methionine aminopeptidase	P0AE18	MAP1_ECOLI	Escherichia coli	3	0.8791
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.8787
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	4	0.8731
Putative ketoacyl reductase	P16544	ACT3_STRCO	Streptomyces coelicolor / M145)	3	0.8709
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.8662
Mitogen-activated protein kinase 10	P53779	MK10_HUMAN	Homo sapiens	3	0.8630
Succinate dehydrogenase flavoprotein subunit	P0AC41	SDHA_ECOLI	Escherichia coli	3	0.8621
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.8601
Tyrosine-protein kinase JAK2	O60674	JAK2_HUMAN	Homo sapiens	3	0.8577
Bromodomain-containing protein 2	P25440	BRD2_HUMAN	Homo sapiens	3	0.8571
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	3	0.8503
Casein kinase II subunit alpha	P68400	CSK21_HUMAN	Homo sapiens	3	0.8492
Steroid Delta-isomerase	P07445	SDIS_PSEPU	Pseudomonas putida	3	0.8469
Biflaviolin synthase CYP158A1	Q9KZF5	C1581_STRCO	Streptomyces coelicolor / M145)	3	0.8395
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.8379
Serine/threonine-protein kinase pim-1	P11309	PIM1_HUMAN	Homo sapiens	3	0.8356
Proto-oncogene tyrosine-protein kinase Src	P12931	SRC_HUMAN	Homo sapiens	3	0.8349
Glycylpeptide N-tetradecanoyltransferase	Q4Q5S8	Q4Q5S8_LEIMA	Leishmania major	3	0.8322
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase	Q9TQS6	DHDH_MACFA	Macaca fascicularis	3	0.8309
Tubulin alpha chain	D0VWZ0	D0VWZ0_SHEEP	Ovis aries	3	0.8256
Soluble acetylcholine receptor	Q8WSF8	Q8WSF8_APLCA	Aplysia californica	3	0.8240
HTH-type transcriptional regulator QacR	P0A0N4	QACR_STAAU	Staphylococcus aureus	3	0.8230
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	3	0.8226
Casein kinase II subunit alpha	P28523	CSK2A_MAIZE	Zea mays	3	0.8175
Aldo-keto reductase family 1 member B1	P15121	ALDR_HUMAN	Homo sapiens	3	0.8102
Mycinamicin III 3''-O-methyltransferase	Q49492	MYCF_MICGR	Micromonospora griseorubida	2	0.8090
Proto-oncogene tyrosine-protein kinase Src	P12931	SRC_HUMAN	Homo sapiens	3	0.8084
Methionine aminopeptidase	P0AE18	MAP1_ECOLI	Escherichia coli	3	0.8067
Activin receptor type-1	Q04771	ACVR1_HUMAN	Homo sapiens	3	0.8067
Toxoflavin degrading enzyme	E3SET7	E3SET7_PAEPO	Paenibacillus polymyxa	3	0.8048
Sex hormone-binding globulin	P04278	SHBG_HUMAN	Homo sapiens	3	0.8030
Ribosyldihydronicotinamide dehydrogenase [quinone]	P16083	NQO2_HUMAN	Homo sapiens	3	0.8004
Casein kinase II subunit alpha	P68400	CSK21_HUMAN	Homo sapiens	3	0.7988
Riboflavin synthase	P0AFU8	RISA_ECOLI	Escherichia coli	3	0.7976
Homoserine dehydrogenase	P31116	DHOM_YEAST	Saccharomyces cerevisiae	3	0.7973
Steroid Delta-isomerase	P07445	SDIS_PSEPU	Pseudomonas putida	3	0.7973
Thymidine kinase	P0DTH5	KITH_HHV11	Human herpesvirus 1	3	0.7948
Bromodomain-containing protein 4	O60885	BRD4_HUMAN	Homo sapiens	3	0.7947
Steroid Delta-isomerase	P07445	SDIS_PSEPU	Pseudomonas putida	3	0.7945
Aldo-keto reductase family 1 member B10	O60218	AK1BA_HUMAN	Homo sapiens	3	0.7932
Enoyl-ACP reductase	Q9BJJ9	Q9BJJ9_PLAFA	Plasmodium falciparum	3	0.7922
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.7881
Biphenyl dioxygenase subunit alpha	P37333	BPHA_PARXL	Paraburkholderia xenovorans	3	0.7866
Trichothecene 15-O-acetyltransferase TRI3	Q9C1B7	TRI3_FUSSP	Fusarium sporotrichioides	3	0.7865
Aldo-keto reductase family 1 member B1	P15121	ALDR_HUMAN	Homo sapiens	3	0.7819
Gag-Pol polyprotein	P03366	POL_HV1B1	Human immunodeficiency virus type 1 group M subtype B	3	0.7816
Bromodomain-containing protein 4	O60885	BRD4_HUMAN	Homo sapiens	3	0.7816
Prostaglandin G/H synthase 2	Q05769	PGH2_MOUSE	Mus musculus	3	0.7809
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	2	0.7794
Serine/threonine-protein kinase pim-1	P11309	PIM1_HUMAN	Homo sapiens	3	0.7766
Methionine aminopeptidase	P0AE18	MAP1_ECOLI	Escherichia coli	3	0.7699
Steroid Delta-isomerase	P07445	SDIS_PSEPU	Pseudomonas putida	3	0.7683
ActVA 6 protein	Q53908	Q53908_STRCH	Streptomyces coelicolor	3	0.7680
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	2	0.7660
Focal adhesion kinase 1	Q00944	FAK1_CHICK	Gallus gallus	3	0.7644
Steroid Delta-isomerase	P00947	SDIS_COMTE	Comamonas testosteroni	3	0.7603
Endoplasmin	P14625	ENPL_HUMAN	Homo sapiens	3	0.7600
Casein kinase II subunit alpha'	P19784	CSK22_HUMAN	Homo sapiens	3	0.7600
Ribosyldihydronicotinamide dehydrogenase [quinone]	P16083	NQO2_HUMAN	Homo sapiens	3	0.7600
Aldo-keto reductase family 1 member C2	P52895	AK1C2_HUMAN	Homo sapiens	3	0.7599
Steroid Delta-isomerase	P00947	SDIS_COMTE	Comamonas testosteroni	3	0.7590
Steroid Delta-isomerase	P07445	SDIS_PSEPU	Pseudomonas putida	2	0.7585
Chitinase A	Q9AMP1	Q9AMP1_VIBHA	Vibrio harveyi	2	0.7583
Dipeptidyl peptidase 4	P27487	DPP4_HUMAN	Homo sapiens	3	0.7581
Acetylcholinesterase	P21836	ACES_MOUSE	Mus musculus	2	0.7574
NAD-capped RNA hydrolase NudC	P32664	NUDC_ECOLI	Escherichia coli	3	0.7561
Aklavinone 12-hydroxylase RdmE	Q54530	DNRF_STREF	Streptomyces purpurascens	4	0.7556
Peptidyl-prolyl cis-trans isomerase FKBP5	Q13451	FKBP5_HUMAN	Homo sapiens	3	0.7545
Thymidylate synthase	P00469	TYSY_LACCA	Lacticaseibacillus casei	2	0.7541
Deoxynucleoside kinase	Q9XZT6	DNK_DROME	Drosophila melanogaster	5	0.7536
Bifunctional dihydrofolate reductase-thymidylate synthase	P13922	DRTS_PLAFK	Plasmodium falciparum	2	0.7535
Tubulin alpha chain	D0VWZ0	D0VWZ0_SHEEP	Ovis aries	4	0.7530
Focal adhesion kinase 1	Q00944	FAK1_CHICK	Gallus gallus	3	0.7526
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.7526
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A	Q9Y233	PDE10_HUMAN	Homo sapiens	3	0.7514
3-phosphoinositide-dependent protein kinase 1	O15530	PDPK1_HUMAN	Homo sapiens	3	0.7513
Tubulin alpha-1B chain	P81947	TBA1B_BOVIN	Bos taurus	3	0.7501
Thymidine kinase	P0DTH5	KITH_HHV11	Human herpesvirus 1	2	0.7488
NAD(P)H dehydrogenase [quinone] 1	P15559	NQO1_HUMAN	Homo sapiens	3	0.7487
Focal adhesion kinase 1	Q00944	FAK1_CHICK	Gallus gallus	3	0.7481
Death-associated protein kinase 1	P53355	DAPK1_HUMAN	Homo sapiens	3	0.7468
Lactotransferrin	P24627	TRFL_BOVIN	Bos taurus	2	0.7464
Bromodomain-containing protein 2	P25440	BRD2_HUMAN	Homo sapiens	3	0.7461
Casein kinase II subunit alpha	P28523	CSK2A_MAIZE	Zea mays	3	0.7459
Tyrosine-protein kinase Lck	P06239	LCK_HUMAN	Homo sapiens	3	0.7451
Cyclin-dependent kinase 2	P24941	CDK2_HUMAN	Homo sapiens	3	0.7432
Serine/threonine-protein kinase 24	Q9Y6E0	STK24_HUMAN	Homo sapiens	3	0.7416
Serine/threonine-protein kinase Chk1	O14757	CHK1_HUMAN	Homo sapiens	3	0.7409
CREB-binding protein	Q92793	CBP_HUMAN	Homo sapiens	3	0.7406
Casein kinase II subunit alpha	P68400	CSK21_HUMAN	Homo sapiens	4	0.7390
Bromodomain-containing protein 4	O60885	BRD4_HUMAN	Homo sapiens	3	0.7364
Biflaviolin synthase CYP158A2	Q9FCA6	C1582_STRCO	Streptomyces coelicolor / M145)	3	0.7327
Serine/threonine-protein kinase Chk1	O14757	CHK1_HUMAN	Homo sapiens	3	0.7323
Casein kinase II subunit alpha	P68400	CSK21_HUMAN	Homo sapiens	3	0.7309
Aldo-keto reductase family 1 member C2	P52895	AK1C2_HUMAN	Homo sapiens	2	0.7306
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform	P48736	PK3CG_HUMAN	Homo sapiens	3	0.7300
Aldo-keto reductase family 1 member B1	P15121	ALDR_HUMAN	Homo sapiens	3	0.7300
Catechol O-methyltransferase	P22734	COMT_RAT	Rattus norvegicus	3	0.7287
Casein kinase II subunit alpha	P68400	CSK21_HUMAN	Homo sapiens	3	0.7271
APH(2'')-Id	O68183	O68183_ENTCA	Enterococcus casseliflavus	3	0.7268
Thymidylate synthase	P0A886	TYSY_ECO57	Escherichia coli O157:H7	2	0.7261
Albumin	P02768	ALBU_HUMAN	Homo sapiens	3	0.7246
Jasmonoyl--L-amino acid synthetase JAR1	Q9SKE2	JAR1_ARATH	Arabidopsis thaliana	3	0.7245
Bromodomain testis-specific protein	Q58F21	BRDT_HUMAN	Homo sapiens	3	0.7244
Cyclin-dependent kinase 2	P24941	CDK2_HUMAN	Homo sapiens	3	0.7224
Ribosyldihydronicotinamide dehydrogenase [quinone]	P16083	NQO2_HUMAN	Homo sapiens	3	0.7221
Ferrochelatase, mitochondrial	P22830	HEMH_HUMAN	Homo sapiens	2	0.7220
Aldo-keto reductase family 1 member B1	P80276	ALDR_PIG	Sus scrofa	3	0.7219
Genome polyprotein	O92972	POLG_HCVJ4	Hepatitis C virus genotype 1b	3	0.7218
Adenosine kinase	P55263	ADK_HUMAN	Homo sapiens	3	0.7210
Acetylcholinesterase	P04058	ACES_TETCF	Tetronarce californica	3	0.7204
3-phosphoinositide-dependent protein kinase 1	O15530	PDPK1_HUMAN	Homo sapiens	3	0.7197
Proliferating cell nuclear antigen	P12004	PCNA_HUMAN	Homo sapiens	3	0.7197
Aldo-keto reductase family 1 member C2	P52895	AK1C2_HUMAN	Homo sapiens	3	0.7192
Soluble acetylcholine receptor	Q8WSF8	Q8WSF8_APLCA	Aplysia californica	2	0.7169
Steroid Delta-isomerase	P00947	SDIS_COMTE	Comamonas testosteroni	2	0.7162
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	3	0.7154
Cholinesterase	P06276	CHLE_HUMAN	Homo sapiens	2	0.7147
F420-dependent methylenetetrahydromethanopterin dehydrogenase	P94951	MTD_METKA	Methanopyrus kandleri	2	0.7139
Cyclin-dependent kinase 2	P24941	CDK2_HUMAN	Homo sapiens	3	0.7135
Bromodomain-containing protein 4	O60885	BRD4_HUMAN	Homo sapiens	3	0.7118
Nucleoprotein	P33469	NCAP_CVHOC	Human coronavirus OC43	3	0.7101
Serine/threonine-protein kinase Chk1	O14757	CHK1_HUMAN	Homo sapiens	3	0.7101
Albumin	P02768	ALBU_HUMAN	Homo sapiens	2	0.7099
Casein kinase II subunit alpha	P68400	CSK21_HUMAN	Homo sapiens	3	0.7095
17-beta-hydroxysteroid dehydrogenase type 1	P14061	DHB1_HUMAN	Homo sapiens	2	0.7090
Bromodomain-containing protein 4	O60885	BRD4_HUMAN	Homo sapiens	3	0.7082
Casein kinase II subunit alpha	P28523	CSK2A_MAIZE	Zea mays	3	0.7082
Casein kinase I isoform gamma-3	Q9Y6M4	KC1G3_HUMAN	Homo sapiens	3	0.7080
Ceramide transfer protein	Q9Y5P4	CERT_HUMAN	Homo sapiens	3	0.7077
Type IV / VI secretion system DotU domain-containing protein	Q9KN50	Q9KN50_VIBCH	Vibrio cholerae serotype O1	2	0.7073
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	2	0.7070
Renin	P00797	RENI_HUMAN	Homo sapiens	2	0.7066
Beta-1 adrenergic receptor	P07700	ADRB1_MELGA	Meleagris gallopavo	3	0.7043
11-beta-hydroxysteroid dehydrogenase 1	P28845	DHI1_HUMAN	Homo sapiens	3	0.7039
Bromodomain-containing protein 4	O60885	BRD4_HUMAN	Homo sapiens	3	0.7037
Lactotransferrin	P24627	TRFL_BOVIN	Bos taurus	2	0.7036
F420-dependent NADP reductase	O29370	FNO_ARCFU	Archaeoglobus fulgidus	3	0.7029
Agglutinin alpha chain	P18674	LECA_MACPO	Maclura pomifera	3	0.7028

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