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Tecleaverdoornine

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

Canonical Smiles	COc1c2c(CC=C(C)C)c3OCOc3c(c2nc2c1cco2)O
InChI	InChI=1S/C18H17NO5/c1-9(2)4-5-10-12-13(14(20)17-16(10)23-8-24-17)19-18-11(6-7-22-18)15(12)21-3/h4,6-7,20H,5,8H2,1-3H3
InChIKey	DVYGQAMJPXHFED-UHFFFAOYSA-N
Formula	C₁₈H₁₇NO₅
HBA	6
HBD	1
MW	327.34
Rotatable Bonds	3
TPSA	73.95
LogP	3.93
Number Rings	4
Number Aromatic Rings	3
Heavy Atom Count	24
Formal Charge	0
Fraction CSP3	0.28
Exact Mass	327.11
Number of Lipinski Rule Violations	0

#	Species	Family	Kingdom	NCBI Taxonomy ID
1	Terminalia ivorensis	Rutaceae	Plantae	578550

Showing of synonyms

Wansi JD, Hussain H, et al. (2010). Antiplasmodial activities of furoquinoline alkaloids from Teclea afzelii.. Phytotherapy research : PTR,2010, 24(5), 775-777. [View] [PubMed]

Pubchem: 152710

Cas: 65847-03-2

Zinc: ZINC000013282232

Nmrshiftdb2: 60072345

Chembl: CHEMBL572482

Comptox: DTXSID10216039

No compound-protein relationship available.

SMILES: c1coc(c12)nc3c(c2)cc4c(c3)OCO4

Level: 0

Mol. Weight: 327.34 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp): -4.54
Human Oral Bioavailability 20%: Bioavailable
Human Intestinal Absorption: Absorbed
Madin-Darby Canine Kidney: -4.62
Human Oral Bioavailability 50%: Bioavailable
P-Glycoprotein Inhibitor: Non-Inhibitor
P-Glycoprotein Substrate: Non-Substrate
Skin Permeability: -1.33

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Penetrable
Fraction Unbound (Human): 1.22
Plasma Protein Binding: 89.19
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: 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: 13.04
Organic Cation Transporter 2: Non-Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Safe
Avian: Safe
Bee: Toxic
Bioconcentration Factor: 1.78
Biodegradation: Safe
Carcinogenesis: Safe
Crustacean: Toxic
Liver Injury I (DILI): Safe
Eye Corrosion: Safe
Eye Irritation: Safe
Maximum Tolerated Dose: -0.22
Liver Injury II: Toxic
hERG Blockers: Safe
Daphnia Maga: 6.27
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: 1.14
Rat (Acute): 2.47
Rat (Chronic Oral): 2.36
Fathead Minnow: 5.12
Respiratory Disease: Toxic
Skin Sensitisation: Safe
SR-ARE: Safe
SR-ATAD5: Safe
SR-HSE: Safe
SR-MMP: Safe
SR-p53: Toxic

General Properties

Boiling Point: 439.19
Hydration Free Energy: -9.0
Log(D) at pH=7.4: 3.55
Log(P): 4.69
Log S: -5.08
Log(Vapor Pressure): -7.83
Melting Point: 155.17
pKa Acid: 7.66
pKa Basic: 5.95

Protein Name	UniProt ID	Entry Name	Species	#Pharmacophore Points	Probability (0.7 ≤ Tversky Score ≤ 1.0)
Riboflavin synthase	P0AFU8	RISA_ECOLI	Escherichia coli	4	0.9383
Alpha-ketoglutarate-dependent dioxygenase FTO	Q9C0B1	FTO_HUMAN	Homo sapiens	3	0.9368
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.9273
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.9163
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.9140
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	3	0.8952
Biflaviolin synthase CYP158A1	Q9KZF5	C1581_STRCO	Streptomyces coelicolor / M145)	3	0.8805
Protein ppBat	Q8A8A4	Q8A8A4_BACTN	Bacteroides thetaiotaomicron VPI-5482	3	0.8758
Chitinase A	Q9AMP1	Q9AMP1_VIBHA	Vibrio harveyi	3	0.8741
Cyclin-dependent kinase 2	P24941	CDK2_HUMAN	Homo sapiens	4	0.8655
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase	Q9TQS6	DHDH_MACFA	Macaca fascicularis	3	0.8633
Toxoflavin degrading enzyme	E3SET7	E3SET7_PAEPO	Paenibacillus polymyxa	3	0.8552
Tubulin alpha chain	D0VWZ0	D0VWZ0_SHEEP	Ovis aries	3	0.8498
Casein kinase I isoform gamma-3	Q9Y6M4	KC1G3_HUMAN	Homo sapiens	4	0.8416
Proliferating cell nuclear antigen	P12004	PCNA_HUMAN	Homo sapiens	3	0.8376
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.8357
Fatty acid-binding protein, intestinal	P12104	FABPI_HUMAN	Homo sapiens	3	0.8261
Cyclin-dependent kinase 2	P24941	CDK2_HUMAN	Homo sapiens	4	0.8246
Chitinase A	Q9AMP1	Q9AMP1_VIBHA	Vibrio harveyi	3	0.8182
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	3	0.8129
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.8054
Cyclin-dependent kinase 2	P24941	CDK2_HUMAN	Homo sapiens	4	0.8001
rRNA N-glycosylase	D9J2T9	D9J2T9_MOMBA	Momordica balsamina	3	0.7991
Casein kinase II subunit alpha	P68400	CSK21_HUMAN	Homo sapiens	3	0.7946
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	3	0.7921
Ribosyldihydronicotinamide dehydrogenase [quinone]	P16083	NQO2_HUMAN	Homo sapiens	3	0.7875
Serine/threonine-protein kinase pim-1	P11309	PIM1_HUMAN	Homo sapiens	3	0.7874
Estrogen receptor	P03372	ESR1_HUMAN	Homo sapiens	3	0.7868
Dipeptidyl peptidase 4	P27487	DPP4_HUMAN	Homo sapiens	3	0.7841
Serine/threonine-protein kinase pim-1	P11309	PIM1_HUMAN	Homo sapiens	3	0.7806
Tyrosine-protein kinase Lck	P06239	LCK_HUMAN	Homo sapiens	3	0.7799
Phosphodiesterase	Q53I60	Q53I60_TRYCR	Trypanosoma cruzi	4	0.7781
Lactotransferrin	P24627	TRFL_BOVIN	Bos taurus	2	0.7742
Mycocyclosin synthase	P9WPP7	CP121_MYCTU	Mycobacterium tuberculosis	2	0.7739
Cathepsin S	P25774	CATS_HUMAN	Homo sapiens	3	0.7738
Aurora kinase B-A	Q6DE08	AUKBA_XENLA	Xenopus laevis	3	0.7735
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A	O76083	PDE9A_HUMAN	Homo sapiens	4	0.7726
Bifunctional dihydrofolate reductase-thymidylate synthase	O02604	DRTS_PLAVI	Plasmodium vivax	3	0.7659
Lethal(3)malignant brain tumor-like protein 1	Q9Y468	LMBL1_HUMAN	Homo sapiens	3	0.7643
Succinate dehydrogenase flavoprotein subunit	P0AC41	SDHA_ECOLI	Escherichia coli	3	0.7638
Lactotransferrin	P24627	TRFL_BOVIN	Bos taurus	3	0.7637
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A	O76083	PDE9A_HUMAN	Homo sapiens	4	0.7628
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform	P48736	PK3CG_HUMAN	Homo sapiens	3	0.7628
Lysozyme C II	P11941	LYSC2_ONCMY	Oncorhynchus mykiss	3	0.7613
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	2	0.7608
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	2	0.7605
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.7603
Nuclear receptor ROR-gamma	P51449	RORG_HUMAN	Homo sapiens	3	0.7587
Transcriptional regulator, PadR-like family	A2RI36	A2RI36_LACLM	Lactococcus lactis subsp. cremoris	2	0.7571
Dodecin	Q5SIE3	DODEC_THET8	Thermus thermophilus	4	0.7565
Soluble acetylcholine receptor	Q8WSF8	Q8WSF8_APLCA	Aplysia californica	3	0.7554
Tyrosine-protein kinase JAK2	O60674	JAK2_HUMAN	Homo sapiens	3	0.7549
11-beta-hydroxysteroid dehydrogenase 1	P28845	DHI1_HUMAN	Homo sapiens	3	0.7543
Uncharacterized protein YML079W	Q03629	YMH9_YEAST	Saccharomyces cerevisiae	3	0.7518
Tubulin alpha-1B chain	P81947	TBA1B_BOVIN	Bos taurus	3	0.7514
Angiotensin-converting enzyme 2	Q9BYF1	ACE2_HUMAN	Homo sapiens	2	0.7493
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform	O02697	PK3CG_PIG	Sus scrofa	3	0.7476
Ribonuclease J	H9CZL7	H9CZL7_DEIRD	Deinococcus radiodurans	3	0.7476
Prostaglandin reductase 2	Q8N8N7	PTGR2_HUMAN	Homo sapiens	3	0.7446
Aldo-keto reductase family 1 member C3	P42330	AK1C3_HUMAN	Homo sapiens	3	0.7426
Aurora kinase A	O14965	AURKA_HUMAN	Homo sapiens	3	0.7416
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	3	0.7404
Focal adhesion kinase 1	Q00944	FAK1_CHICK	Gallus gallus	3	0.7381
cGMP-specific 3',5'-cyclic phosphodiesterase	O76074	PDE5A_HUMAN	Homo sapiens	4	0.7376
Protein mono-ADP-ribosyltransferase PARP3	Q9Y6F1	PARP3_HUMAN	Homo sapiens	3	0.7364
cGMP-dependent protein kinase, putative	A5K0N4	A5K0N4_PLAVS	Plasmodium vivax	3	0.7340
Cytosolic purine 5'-nucleotidase	P49902	5NTC_HUMAN	Homo sapiens	2	0.7339
DNA ligase	P43813	DNLJ_HAEIN	Haemophilus influenzae	2	0.7325
Serine/threonine-protein kinase Chk1	O14757	CHK1_HUMAN	Homo sapiens	3	0.7310
p-hydroxyphenylacetate 3-hydroxylase, oxygenase component	Q6Q272	HPAH_ACIBA	Acinetobacter baumannii	4	0.7309
Catalase-peroxidase 2	O59651	KATG2_HALMA	Haloarcula marismortui	2	0.7286
Focal adhesion kinase 1	Q00944	FAK1_CHICK	Gallus gallus	3	0.7252
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	2	0.7249
Riboflavin biosynthesis protein	Q9WZW1	Q9WZW1_THEMA	Thermotoga maritima	3	0.7247
Aldo-keto reductase family 1 member B1	P15121	ALDR_HUMAN	Homo sapiens	2	0.7246
Putative HMP/thiamine-binding protein YkoF	O34911	YKOF_BACSU	Bacillus subtilis	3	0.7236
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A	O76083	PDE9A_HUMAN	Homo sapiens	4	0.7233
Succinate dehydrogenase flavoprotein subunit	P0AC41	SDHA_ECOLI	Escherichia coli	3	0.7232
Tyrosine-protein kinase Lck	P06239	LCK_HUMAN	Homo sapiens	4	0.7228
Tyrosine-protein kinase Lck	P06239	LCK_HUMAN	Homo sapiens	3	0.7221
Gag-Pol polyprotein	P05896	POL_SIVM1	Simian immunodeficiency virus	3	0.7206
Sulfide-quinone reductase	B7JBP8	SQRD_ACIF2	Acidithiobacillus ferrooxidans)	3	0.7188
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A	Q9Y233	PDE10_HUMAN	Homo sapiens	3	0.7187
GCN5-related N-acetyltransferase	B1YEL6	B1YEL6_EXIS2	Exiguobacterium sibiricum	3	0.7184
Pteridine reductase 1	Q01782	PTR1_LEIMA	Leishmania major	3	0.7180
Cell division cycle 7-related protein kinase	O00311	CDC7_HUMAN	Homo sapiens	3	0.7178
Focal adhesion kinase 1	Q00944	FAK1_CHICK	Gallus gallus	3	0.7158
Cyclin-dependent kinase 2	P24941	CDK2_HUMAN	Homo sapiens	4	0.7156
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.7144
Pteridine reductase, putative	Q581W1	Q581W1_TRYB2	Trypanosoma brucei brucei	3	0.7134
Cholinesterase	P06276	CHLE_HUMAN	Homo sapiens	2	0.7130
Tyrosine-protein kinase HCK	P08631	HCK_HUMAN	Homo sapiens	3	0.7111
GCN5-related N-acetyltransferase	B1YEL6	B1YEL6_EXIS2	Exiguobacterium sibiricum	3	0.7105
NADPH dehydrogenase 1	Q02899	OYE1_SACPS	Saccharomyces pastorianus	3	0.7084
Deoxycytidine kinase	P27707	DCK_HUMAN	Homo sapiens	4	0.7064
Aklavinone 12-hydroxylase RdmE	Q54530	DNRF_STREF	Streptomyces purpurascens	4	0.7059
Thymidylate synthase	P00469	TYSY_LACCA	Lacticaseibacillus casei	2	0.7048
F420-dependent methylenetetrahydromethanopterin dehydrogenase	P94951	MTD_METKA	Methanopyrus kandleri	2	0.7038
Nucleoprotein	P33469	NCAP_CVHOC	Human coronavirus OC43	3	0.7034
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	2	0.7033
Genome polyprotein	O92972	POLG_HCVJ4	Hepatitis C virus genotype 1b	3	0.7032
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic	Q43088	RBCMT_PEA	Pisum sativum	3	0.7030
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	2	0.7029
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.7026

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