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Helebelicine A

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

Canonical Smiles	COc1cc(O)c(c2c1c(=O)c1c(n2C)cccc1)OC
InChI	InChI=1S/C16H15NO4/c1-17-10-7-5-4-6-9(10)15(19)13-12(20-2)8-11(18)16(21-3)14(13)17/h4-8,18H,1-3H3
InChIKey	IUSDGCPJUCVNHX-UHFFFAOYSA-N
Formula	C₁₆H₁₅NO₄
HBA	5
HBD	1
MW	285.3
Rotatable Bonds	2
TPSA	60.69
LogP	2.41
Number Rings	3
Number Aromatic Rings	3
Heavy Atom Count	21
Formal Charge	0
Fraction CSP3	0.19
Exact Mass	285.1
Number of Lipinski Rule Violations	0

#	Species	Family	Kingdom	NCBI Taxonomy ID
1	Zanthoxylum leprieurii	Rutaceae	Plantae	992815

Showing of synonyms

Fomani M, Ngeufa Happi E, et al. (2016). Oxidative burst inhibition, cytotoxicity and antibacterial acriquinoline alkaloids from Citrus reticulate (Blanco).. Bioorganic & medicinal chemistry letters,2016, 26(2), 306-309. [View] [PubMed]

Pubchem: 46887583

Zinc: ZINC000049109390

Nmrshiftdb2: 60028690

Chembl: CHEMBL1095074

No compound-protein relationship available.

SMILES: c1cccc(c12)[nH]c3c(c2=O)cccc3

Level: 0

Mol. Weight: 285.3 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp): -4.54
Human Oral Bioavailability 20%: Bioavailable
Human Intestinal Absorption: Absorbed
Madin-Darby Canine Kidney: -4.250
Human Oral Bioavailability 50%: Bioavailable
P-Glycoprotein Inhibitor: Inhibitor
P-Glycoprotein Substrate: Non-Substrate
Skin Permeability: -1.94

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Penetrable
Fraction Unbound (Human): 1.450
Plasma Protein Binding: 65.14
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: Non-Inhibitor
CYP 2D6 Substrate: Non-Substrate
CYP 3A4 Inhibitor: Inhibitor
CYP 3A4 Substrate: Non-Substrate
OATP1B1: Non-Inhibitor
OATP1B3: Non-Inhibitor

Excretion

Clearance: 2.920
Organic Cation Transporter 2: Non-Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Toxic
Avian: Safe
Bee: Safe
Bioconcentration Factor: 1.500
Biodegradation: Safe
Carcinogenesis: Safe
Crustacean: Toxic
Liver Injury I (DILI): Toxic
Eye Corrosion: Safe
Eye Irritation: Safe
Maximum Tolerated Dose: 0.360
Liver Injury II: Toxic
hERG Blockers: Safe
Daphnia Maga: 4.420
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: 3.950
Rat (Acute): 2.220
Rat (Chronic Oral): 2.280
Fathead Minnow: 4.920
Respiratory Disease: Toxic
Skin Sensitisation: Safe
SR-ARE: Toxic
SR-ATAD5: Safe
SR-HSE: Safe
SR-MMP: Toxic
SR-p53: Toxic

General Properties

Boiling Point: 411.680
Hydration Free Energy: -9.690
Log(D) at pH=7.4: 1.410
Log(P): 2.26
Log S: -4.16
Log(Vapor Pressure): -6.94
Melting Point: 207.92
pKa Acid: 6.67
pKa Basic: 4.43

Protein Name	UniProt ID	Entry Name	Species	#Pharmacophore Points	Probability (0.7 ≤ Tversky Score ≤ 1.0)
Riboflavin synthase	P0AFU8	RISA_ECOLI	Escherichia coli	4	0.9703
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A	Q9Y233	PDE10_HUMAN	Homo sapiens	3	0.9251
Biflaviolin synthase CYP158A1	Q9KZF5	C1581_STRCO	Streptomyces coelicolor / M145)	3	0.9200
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase	Q9TQS6	DHDH_MACFA	Macaca fascicularis	3	0.9022
Aromatic-amino-acid aminotransferase	P95468	TYRB_PARDE	Paracoccus denitrificans	3	0.8964
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.8885
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A	Q9Y233	PDE10_HUMAN	Homo sapiens	3	0.8782
Alpha-ketoglutarate-dependent dioxygenase FTO	Q9C0B1	FTO_HUMAN	Homo sapiens	3	0.8767
Tetracycline repressor protein class H	P51561	TETR8_PASMD	Pasteurella multocida	3	0.8703
Mitogen-activated protein kinase 10	P53779	MK10_HUMAN	Homo sapiens	3	0.8676
Albumin	P02768	ALBU_HUMAN	Homo sapiens	3	0.8630
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.8562
Methionine aminopeptidase	P0AE18	MAP1_ECOLI	Escherichia coli	3	0.8513
Serine/threonine-protein kinase pim-1	P11309	PIM1_HUMAN	Homo sapiens	3	0.8511
Sex hormone-binding globulin	P04278	SHBG_HUMAN	Homo sapiens	3	0.8496
Biflaviolin synthase CYP158A2	Q9FCA6	C1582_STRCO	Streptomyces coelicolor / M145)	3	0.8494
Ribosomal small subunit pseudouridine synthase A	P0AA43	RSUA_ECOLI	Escherichia coli	3	0.8475
Methionine aminopeptidase 2	P9WK19	MAP12_MYCTU	Mycobacterium tuberculosis	3	0.8415
Tyrosine-protein kinase JAK2	O60674	JAK2_HUMAN	Homo sapiens	3	0.8369
Toxoflavin degrading enzyme	E3SET7	E3SET7_PAEPO	Paenibacillus polymyxa	3	0.8333
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.8285
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.8241
Biflaviolin synthase CYP158A2	Q9FCA6	C1582_STRCO	Streptomyces coelicolor / M145)	3	0.8175
Tubulin alpha chain	D0VWZ0	D0VWZ0_SHEEP	Ovis aries	3	0.8142
Tubulin alpha-1B chain	P81947	TBA1B_BOVIN	Bos taurus	3	0.7991
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	4	0.7970
Casein kinase II subunit alpha'	P19784	CSK22_HUMAN	Homo sapiens	3	0.7925
Catechol O-methyltransferase	P22734	COMT_RAT	Rattus norvegicus	3	0.7712
Casein kinase I isoform gamma-3	Q9Y6M4	KC1G3_HUMAN	Homo sapiens	3	0.7655
Ribosyldihydronicotinamide dehydrogenase [quinone]	P16083	NQO2_HUMAN	Homo sapiens	3	0.7639
Fatty acid-binding protein, intestinal	P12104	FABPI_HUMAN	Homo sapiens	3	0.7559
Casein kinase II subunit alpha	P68400	CSK21_HUMAN	Homo sapiens	3	0.7545
ActVA 6 protein	Q53908	Q53908_STRCH	Streptomyces coelicolor	3	0.7491
Sex hormone-binding globulin	P04278	SHBG_HUMAN	Homo sapiens	3	0.7479
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.7470
Steroid Delta-isomerase	P07445	SDIS_PSEPU	Pseudomonas putida	3	0.7470
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	2	0.7464
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.7454
Ribosyldihydronicotinamide dehydrogenase [quinone]	P16083	NQO2_HUMAN	Homo sapiens	3	0.7448
Casein kinase II subunit alpha	P68400	CSK21_HUMAN	Homo sapiens	3	0.7438
Methionine aminopeptidase	P0AE18	MAP1_ECOLI	Escherichia coli	3	0.7432
Mandelate racemase	P11444	MANR_PSEPU	Pseudomonas putida	3	0.7406
Dipeptidyl peptidase 4	P27487	DPP4_HUMAN	Homo sapiens	3	0.7405
Homoserine dehydrogenase	P31116	DHOM_YEAST	Saccharomyces cerevisiae	3	0.7404
Biphenyl dioxygenase subunit alpha	P37333	BPHA_PARXL	Paraburkholderia xenovorans	3	0.7400
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.7391
Genome polyprotein	O92972	POLG_HCVJ4	Hepatitis C virus genotype 1b	3	0.7382
Catechol O-methyltransferase	P22734	COMT_RAT	Rattus norvegicus	3	0.7361
Proto-oncogene tyrosine-protein kinase Src	P12931	SRC_HUMAN	Homo sapiens	3	0.7360
Deoxyribodipyrimidine photo-lyase	Q8PYK9	Q8PYK9_METMA	Methanosarcina mazei	4	0.7355
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	2	0.7355
Type IV / VI secretion system DotU domain-containing protein	Q9KN50	Q9KN50_VIBCH	Vibrio cholerae serotype O1	2	0.7353
Aldo-keto reductase family 1 member B1	P15121	ALDR_HUMAN	Homo sapiens	2	0.7309
Serine/threonine-protein kinase 24	Q9Y6E0	STK24_HUMAN	Homo sapiens	3	0.7281
Cyclin-dependent kinase 2	P24941	CDK2_HUMAN	Homo sapiens	3	0.7280
Activin receptor type-1	Q04771	ACVR1_HUMAN	Homo sapiens	3	0.7276
Abscisic acid receptor PYL2	O80992	PYL2_ARATH	Arabidopsis thaliana	2	0.7273
Beta-1 adrenergic receptor	P07700	ADRB1_MELGA	Meleagris gallopavo	3	0.7268
Tyrosine-protein kinase Lck	P06239	LCK_HUMAN	Homo sapiens	3	0.7266
11-beta-hydroxysteroid dehydrogenase 1	P28845	DHI1_HUMAN	Homo sapiens	3	0.7256
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.7254
Glycylpeptide N-tetradecanoyltransferase	Q4Q5S8	Q4Q5S8_LEIMA	Leishmania major	3	0.7247
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.7235
Proto-oncogene tyrosine-protein kinase Src	P12931	SRC_HUMAN	Homo sapiens	3	0.7218
Glutamate receptor 3	P19492	GRIA3_RAT	Rattus norvegicus	3	0.7201
Pheromone-binding protein ASP1	Q9U9J6	Q9U9J6_APIME	Apis mellifera	2	0.7200
Lactotransferrin	P24627	TRFL_BOVIN	Bos taurus	2	0.7190
cGMP-dependent protein kinase 1	Q13976	KGP1_HUMAN	Homo sapiens	2	0.7187
Focal adhesion kinase 1	Q00944	FAK1_CHICK	Gallus gallus	3	0.7182
Aldo-keto reductase family 1 member B10	O60218	AK1BA_HUMAN	Homo sapiens	2	0.7173
Fibroblast growth factor receptor 1	P11362	FGFR1_HUMAN	Homo sapiens	3	0.7170
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	3	0.7159
Ribosyldihydronicotinamide dehydrogenase [quinone]	P16083	NQO2_HUMAN	Homo sapiens	2	0.7153
Ribosyldihydronicotinamide dehydrogenase [quinone]	P16083	NQO2_HUMAN	Homo sapiens	3	0.7144
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.7130
Glycogen synthase	Q9V2J8	Q9V2J8_PYRAB	Pyrococcus abyssi	3	0.7124
cGMP-dependent protein kinase, putative	A5K0N4	A5K0N4_PLAVS	Plasmodium vivax	3	0.7117
Ferrochelatase, mitochondrial	P22830	HEMH_HUMAN	Homo sapiens	3	0.7100
Casein kinase II subunit alpha	P68400	CSK21_HUMAN	Homo sapiens	3	0.7100
Serine/threonine-protein kinase Chk1	O14757	CHK1_HUMAN	Homo sapiens	3	0.7065
Cyclin-dependent kinase 2	P24941	CDK2_HUMAN	Homo sapiens	3	0.7057
Glycogen phosphorylase, muscle form	P00489	PYGM_RABIT	Oryctolagus cuniculus	3	0.7048

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