Helebelicine B - Compound Card

Helebelicine B

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Helebelicine B

Structure
Zoomed Structure
  • Family: Plantae - Rutaceae
  • Kingdom: Plantae
  • Class: Alkaloid
    • Subclass: Acridine Alkaloid
Canonical Smiles COc1c(OC)c(O)cc2c1c(=O)c1c(n2C)cccc1
InChI InChI=1S/C16H15NO4/c1-17-10-7-5-4-6-9(10)14(19)13-11(17)8-12(18)15(20-2)16(13)21-3/h4-8,18H,1-3H3
InChIKey WXZWLRMQBKIQRO-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: 46845028
Nmrshiftdb2: 60028691

No compound-protein relationship available.

Structure

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

Level: 0

Mol. Weight: 285.3 g/mol

Cytotoxic

Absorption

Caco-2 (logPapp)
-4.54
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.230
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.17

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
1.350
Plasma Protein Binding
64.35
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
Substrate
CYP 3A4 Inhibitor
Inhibitor
CYP 3A4 Substrate
Non-Substrate
OATP1B1
Non-Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
3.030
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Safe
Bioconcentration Factor
1.490
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Toxic
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.440
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
4.710
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
3.910
Rat (Acute)
2.220
Rat (Chronic Oral)
2.260
Fathead Minnow
4.900
Respiratory Disease
Toxic
Skin Sensitisation
Safe
SR-ARE
Toxic
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Toxic
SR-p53
Safe

General Properties

Boiling Point
408.830
Hydration Free Energy
-9.650
Log(D) at pH=7.4
1.060
Log(P)
2.03
Log S
-3.87
Log(Vapor Pressure)
-6.77
Melting Point
208.05
pKa Acid
6.01
pKa Basic
3.83
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Alpha-ketoglutarate-dependent dioxygenase FTO Q9C0B1 FTO_HUMAN Homo sapiens 3 0.9616
Riboflavin synthase P0AFU8 RISA_ECOLI Escherichia coli 4 0.9552
2,7-dihydroxy-5-methyl-1-naphthoate 7-O-methyltransferase Q84HC8 NCSB1_STRCZ Streptomyces carzinostaticus 3 0.9459
Putative ketoacyl reductase P16544 ACT3_STRCO Streptomyces coelicolor / M145) 3 0.9367
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.9266
Biflaviolin synthase CYP158A1 Q9KZF5 C1581_STRCO Streptomyces coelicolor / M145) 3 0.9175
Ribosomal small subunit pseudouridine synthase A P0AA43 RSUA_ECOLI Escherichia coli 3 0.9150
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.8976
Biflaviolin synthase CYP158A2 Q9FCA6 C1582_STRCO Streptomyces coelicolor / M145) 3 0.8968
Albumin P02768 ALBU_HUMAN Homo sapiens 3 0.8893
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.8879
Toxoflavin degrading enzyme E3SET7 E3SET7_PAEPO Paenibacillus polymyxa 3 0.8866
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8786
Mitogen-activated protein kinase 10 P53779 MK10_HUMAN Homo sapiens 3 0.8765
Methionine aminopeptidase 2 P9WK19 MAP12_MYCTU Mycobacterium tuberculosis 3 0.8702
Methionine aminopeptidase P0AE18 MAP1_ECOLI Escherichia coli 3 0.8669
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.8653
Serine/threonine-protein kinase pim-1 P11309 PIM1_HUMAN Homo sapiens 3 0.8636
Activin receptor type-1 Q04771 ACVR1_HUMAN Homo sapiens 3 0.8611
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.8607
Biflaviolin synthase CYP158A2 Q9FCA6 C1582_STRCO Streptomyces coelicolor / M145) 3 0.8580
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.8519
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.8518
Carminomycin 4-O-methyltransferase DnrK Q06528 DNRK_STRPE Streptomyces peucetius 3 0.8310
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.8192
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.8173
Tetracycline repressor protein class H P51561 TETR8_PASMD Pasteurella multocida 3 0.8172
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.8033
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 3 0.7968
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 3 0.7922
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.7917
cGMP-dependent protein kinase 2 Q13237 KGP2_HUMAN Homo sapiens 3 0.7907
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7837
Fatty acid-binding protein, intestinal P12104 FABPI_HUMAN Homo sapiens 3 0.7822
Methionine aminopeptidase P0AE18 MAP1_ECOLI Escherichia coli 3 0.7819
Serine/threonine-protein kinase 24 Q9Y6E0 STK24_HUMAN Homo sapiens 3 0.7802
Albumin P02768 ALBU_HUMAN Homo sapiens 3 0.7787
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7773
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 3 0.7737
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7719
Homoserine dehydrogenase P31116 DHOM_YEAST Saccharomyces cerevisiae 3 0.7706
Proto-oncogene tyrosine-protein kinase Src P12931 SRC_HUMAN Homo sapiens 3 0.7701
Tyrosine-protein kinase Lck P06239 LCK_HUMAN Homo sapiens 3 0.7663
Gag-Pol polyprotein P03366 POL_HV1B1 Human immunodeficiency virus type 1 group M subtype B 3 0.7645
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 4 0.7613
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7606
Dipeptidyl peptidase 4 P27487 DPP4_HUMAN Homo sapiens 3 0.7573
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7554
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7554
Methionine aminopeptidase P0AE18 MAP1_ECOLI Escherichia coli 3 0.7544
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7536
Casein kinase I isoform gamma-3 Q9Y6M4 KC1G3_HUMAN Homo sapiens 3 0.7509
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7499
F420-dependent NADP reductase O29370 FNO_ARCFU Archaeoglobus fulgidus 3 0.7499
ActVA 6 protein Q53908 Q53908_STRCH Streptomyces coelicolor 3 0.7493
Focal adhesion kinase 1 Q00944 FAK1_CHICK Gallus gallus 3 0.7467
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7458
Protein ppBat Q8A8A4 Q8A8A4_BACTN Bacteroides thetaiotaomicron VPI-5482 2 0.7448
Focal adhesion kinase 1 Q00944 FAK1_CHICK Gallus gallus 3 0.7428
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7421
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 3 0.7415
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7368
Focal adhesion kinase 1 Q00944 FAK1_CHICK Gallus gallus 3 0.7359
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7334
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7297
Putative protease I Q8A8A4 Q8A8A4_BACTN Bacteroides thetaiotaomicron 2 0.7297
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 3 0.7287
Tubulin alpha chain D0VWZ0 D0VWZ0_SHEEP Ovis aries 3 0.7278
Tubulin alpha-1B chain P81947 TBA1B_BOVIN Bos taurus 3 0.7273
17-beta-hydroxysteroid dehydrogenase 14 Q9BPX1 DHB14_HUMAN Homo sapiens 2 0.7254
cGMP-dependent protein kinase, putative A5K0N4 A5K0N4_PLAVS Plasmodium vivax 3 0.7243
Lethal(3)malignant brain tumor-like protein 1 Q9Y468 LMBL1_HUMAN Homo sapiens 3 0.7233
Proto-oncogene tyrosine-protein kinase Src P12931 SRC_HUMAN Homo sapiens 3 0.7193
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 2 0.7148
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.7142
Activin receptor type-1 Q04771 ACVR1_HUMAN Homo sapiens 3 0.7137
Ephrin type-B receptor 4 P54760 EPHB4_HUMAN Homo sapiens 3 0.7130
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.7128
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7111
Polyprotein Q80J95 Q80J95_9CALI Murine norovirus 1 2 0.7111
Protocatechuate 3,4-dioxygenase beta chain P00437 PCXB_PSEPU Pseudomonas putida 3 0.7100
Genome polyprotein O92972 POLG_HCVJ4 Hepatitis C virus genotype 1b 3 0.7093
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 2 0.7093
Polymerase acidic protein Q5EP34 Q5EP34_9INFA Influenza A virus 2 0.7086
Enoyl-ACP reductase Q9BJJ9 Q9BJJ9_PLAFA Plasmodium falciparum 3 0.7084
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7057
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 2 0.7053
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 2 0.7038
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7016
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7012

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