Maculine B - Compound Card

Maculine B

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Maculine B

Structure
Zoomed Structure
  • Family: Rutaceae
  • Kingdom: Plantae
  • Class: Alkaloid
    • Subclass: Furoquinoline Alkaloid
Canonical Smiles COc1nc2cc3OCOc3cc2c2c1cco2
InChI InChI=1S/C13H9NO4/c1-15-13-7-2-3-16-12(7)8-4-10-11(18-6-17-10)5-9(8)14-13/h2-5H,6H2,1H3
InChIKey VYPBHLUMAVQJMW-UHFFFAOYSA-N
Formula C13H9NO4
HBA 5
HBD 0
MW 243.22
Rotatable Bonds 1
TPSA 53.72
LogP 2.72
Number Rings 4
Number Aromatic Rings 3
Heavy Atom Count 18
Formal Charge 0
Fraction CSP3 0.15
Exact Mass 243.05
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Araliopsis soyauxii Rutaceae Plantae 1317904

Showing of synonyms

  • Nganou BK, Mbaveng AT, et al. (2019). Furoquinolines and dihydrooxazole alkaloids with cytotoxic activity from the stem bark of Araliopsis soyauxii.. Fitoterapia,2019, 133, 193-199. [View] [PubMed]

No compound-protein relationship available.

Structure

SMILES: c1coc(c12)c3c(nc2)cc4c(c3)OCO4

Level: 0

Mol. Weight: 213.19 g/mol

Cytotoxic

Absorption

Caco-2 (logPapp)
-4.63
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.260
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.2

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.790
Plasma Protein Binding
62.21
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
Non-Inhibitor
CYP 2D6 Substrate
Non-Substrate
CYP 3A4 Inhibitor
Inhibitor
CYP 3A4 Substrate
Non-Substrate
OATP1B1
Non-Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
8.530
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Safe
Bioconcentration Factor
1.570
Biodegradation
Safe
Carcinogenesis
Toxic
Crustacean
Toxic
Liver Injury I (DILI)
Toxic
Eye Corrosion
Safe
Eye Irritation
Toxic
Maximum Tolerated Dose
1.320
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
5.130
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
3.850
Rat (Acute)
2.280
Rat (Chronic Oral)
1.820
Fathead Minnow
4.820
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
396.520
Hydration Free Energy
-9.690
Log(D) at pH=7.4
2.770
Log(P)
3.24
Log S
-3.07
Log(Vapor Pressure)
-6.2
Melting Point
168.48
pKa Acid
5.65
pKa Basic
5.11
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Bromodomain-containing protein 2 P25440 BRD2_HUMAN Homo sapiens 3 0.9668
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.9582
2,7-dihydroxy-5-methyl-1-naphthoate 7-O-methyltransferase Q84HC8 NCSB1_STRCZ Streptomyces carzinostaticus 3 0.9556
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 3 0.9541
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.9495
Glycogen phosphorylase, muscle form P00489 PYGM_RABIT Oryctolagus cuniculus 3 0.9481
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.9447
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.9407
cGMP-specific 3',5'-cyclic phosphodiesterase O76074 PDE5A_HUMAN Homo sapiens 3 0.9298
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 3 0.9278
Biflaviolin synthase CYP158A1 Q9KZF5 C1581_STRCO Streptomyces coelicolor / M145) 3 0.9239
CREB-binding protein Q92793 CBP_HUMAN Homo sapiens 3 0.9209
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.9203
Carminomycin 4-O-methyltransferase DnrK Q06528 DNRK_STRPE Streptomyces peucetius 3 0.9075
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 3 0.9068
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.9058
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase Q9TQS6 DHDH_MACFA Macaca fascicularis 3 0.9042
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 3 0.9011
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.8993
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 3 0.8953
Bromodomain adjacent to zinc finger domain protein 2B Q9UIF8 BAZ2B_HUMAN Homo sapiens 3 0.8940
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 3 0.8894
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8893
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 4 0.8879
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 3 0.8872
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.8855
Acetylcholinesterase P22303 ACES_HUMAN Homo sapiens 3 0.8847
Probable esterase KAI2 Q9SZU7 KAI2_ARATH Arabidopsis thaliana 3 0.8830
2-phospho-L-lactate transferase Q8PVT6 COFD_METMA Methanosarcina mazei 3 0.8798
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 3 0.8760
Cytochrome P450 monooxygenase Q5YNS8 Q5YNS8_NOCFA Nocardia farcinica 3 0.8692
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 3 0.8689
Na(+):neurotransmitter symporter (Snf family) O67854 O67854_AQUAE Aquifex aeolicus 3 0.8665
Sulfotransferase 2A1 Q06520 ST2A1_HUMAN Homo sapiens 3 0.8650
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 3 0.8643
Cathepsin S P25774 CATS_HUMAN Homo sapiens 3 0.8608
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 3 0.8596
2,7-dihydroxy-5-methyl-1-naphthoate 7-O-methyltransferase Q84HC8 NCSB1_STRCZ Streptomyces carzinostaticus 3 0.8574
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.8532
Toxoflavin degrading enzyme E3SET7 E3SET7_PAEPO Paenibacillus polymyxa 3 0.8400
NAD-capped RNA hydrolase NudC P32664 NUDC_ECOLI Escherichia coli 3 0.8332
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.8297
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.8285
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.8257
Steroid 21-hydroxylase P08686 CP21A_HUMAN Homo sapiens 3 0.8225
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 3 0.8196
Cytochrome P450 2A6 P11509 CP2A6_HUMAN Homo sapiens 3 0.8160
Aromatase P11511 CP19A_HUMAN Homo sapiens 3 0.8127
Proto-oncogene tyrosine-protein kinase Src P00523 SRC_CHICK Gallus gallus 3 0.8121
Enoyl-ACP reductase Q9BJJ9 Q9BJJ9_PLAFA Plasmodium falciparum 3 0.8094
Putative ketoacyl reductase P16544 ACT3_STRCO Streptomyces coelicolor / M145) 3 0.8064
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.8031
Biphenyl dioxygenase subunit alpha P37333 BPHA_PARXL Paraburkholderia xenovorans 3 0.8017
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8014
Acetylcholine-binding protein P58154 ACHP_LYMST Lymnaea stagnalis 3 0.7997
Cis-2,3-dihydrobiphenyl-2,3-diol dehydrogenase Q46381 BPHB_COMTE Comamonas testosteroni 3 0.7982
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.7969
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7965
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7954
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7951
HTH-type transcriptional regulator EthR P9WMC1 ETHR_MYCTU Mycobacterium tuberculosis 3 0.7944
Biflaviolin synthase CYP158A2 Q9FCA6 C1582_STRCO Streptomyces coelicolor / M145) 3 0.7944
Dihydroorotate dehydrogenase (quinone), mitochondrial Q08210 PYRD_PLAF7 Plasmodium falciparum 3 0.7922
NAD(P)H dehydrogenase [quinone] 1 P15559 NQO1_HUMAN Homo sapiens 3 0.7915
17-beta-hydroxysteroid dehydrogenase type 1 P14061 DHB1_HUMAN Homo sapiens 2 0.7894
Tyrosine-protein kinase Lck P06239 LCK_HUMAN Homo sapiens 3 0.7881
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7864
Biflaviolin synthase CYP158A2 Q9FCA6 C1582_STRCO Streptomyces coelicolor / M145) 3 0.7861
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 2 0.7832
Nitroreductase domain-containing protein Q8DW21 Q8DW21_STRMU Streptococcus mutans serotype c 3 0.7828
Nucleoprotein P33469 NCAP_CVHOC Human coronavirus OC43 3 0.7828
Aldo-keto reductase family 1 member B1 P15121 ALDR_HUMAN Homo sapiens 4 0.7808
3-phosphoinositide-dependent protein kinase 1 O15530 PDPK1_HUMAN Homo sapiens 3 0.7787
Tubulin alpha-1B chain P81947 TBA1B_BOVIN Bos taurus 3 0.7759
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.7749
3-alpha-hydroxysteroid dehydrogenase P23457 DIDH_RAT Rattus norvegicus 3 0.7732
Aromatase P11511 CP19A_HUMAN Homo sapiens 3 0.7721
Genome polyprotein O92972 POLG_HCVJ4 Hepatitis C virus genotype 1b 3 0.7711
Sulfotransferase 2A1 Q06520 ST2A1_HUMAN Homo sapiens 3 0.7707
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7686
Protein mono-ADP-ribosyltransferase PARP3 Q9Y6F1 PARP3_HUMAN Homo sapiens 3 0.7683
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 3 0.7673
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7661
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7649
Death-associated protein kinase 1 P53355 DAPK1_HUMAN Homo sapiens 3 0.7639
Gag-Pol polyprotein P04585 POL_HV1H2 Human immunodeficiency virus type 1 group M subtype B 4 0.7628
Tubulin alpha chain D0VWZ0 D0VWZ0_SHEEP Ovis aries 3 0.7609
Gag-Pol polyprotein P04585 POL_HV1H2 Human immunodeficiency virus type 1 group M subtype B 4 0.7596
Prostaglandin F2a synthase Q8I6L9 Q8I6L9_TRYCR Trypanosoma cruzi 2 0.7596
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 2 0.7594
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.7591
Exotoxin A P11439 TOXA_PSEAE Pseudomonas aeruginosa 3 0.7590
Interleukin-2 P60568 IL2_HUMAN Homo sapiens 2 0.7576
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7575
Sex hormone-binding globulin P04278 SHBG_HUMAN Homo sapiens 3 0.7574
Cholesterol oxidase P22637 CHOD_BREST Brevibacterium sterolicum 3 0.7568
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7567
Retinol dehydratase Q26490 Q26490_SPOFR Spodoptera frugiperda 3 0.7565
Lactoylglutathione lyase Q04760 LGUL_HUMAN Homo sapiens 2 0.7558
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.7556
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.7556
Cytochrome P450 2A6 P11509 CP2A6_HUMAN Homo sapiens 3 0.7528
Fatty acid-binding protein, intestinal P12104 FABPI_HUMAN Homo sapiens 3 0.7515
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 3 0.7512
Acetylcholinesterase P04058 ACES_TETCF Tetronarce californica 3 0.7485
Serine/threonine-protein kinase 24 Q9Y6E0 STK24_HUMAN Homo sapiens 3 0.7483
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7471
Cathepsin S P25774 CATS_HUMAN Homo sapiens 2 0.7468
Agglutinin alpha chain P18674 LECA_MACPO Maclura pomifera 3 0.7453
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7447
Fatty acid-binding protein, liver P80226 FABPL_CHICK Gallus gallus 2 0.7442
ADP compounds hydrolase NudE P45799 NUDE_ECOLI Escherichia coli 2 0.7432
Mitogen-activated protein kinase 14 Q16539 MK14_HUMAN Homo sapiens 2 0.7429
Putative ketoacyl reductase P16544 ACT3_STRCO Streptomyces coelicolor / M145) 2 0.7423
Lethal(3)malignant brain tumor-like protein 1 Q9Y468 LMBL1_HUMAN Homo sapiens 3 0.7410
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 2 0.7399
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 3 0.7393
Tyrosine-protein kinase Lck P06239 LCK_HUMAN Homo sapiens 3 0.7387
Sulfotransferase 2B1 O00204 ST2B1_HUMAN Homo sapiens 2 0.7381
Peptidyl-prolyl cis-trans isomerase FKBP1A P62942 FKB1A_HUMAN Homo sapiens 2 0.7378
Gag-Pol polyprotein P04585 POL_HV1H2 Human immunodeficiency virus type 1 group M subtype B 4 0.7374
Glucose-1-phosphate thymidylyltransferase Q9HU22 Q9HU22_PSEAE Pseudomonas aeruginosa 3 0.7370
Death-associated protein kinase 1 P53355 DAPK1_HUMAN Homo sapiens 3 0.7369
Acetylcholinesterase P04058 ACES_TETCF Tetronarce californica 3 0.7366
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.7351
Phytohormone-binding protein G7J032 PHBP_MEDTR Medicago truncatula 4 0.7347
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 3 0.7346
TDP-4-oxo-6-deoxy-alpha-D-glucose-3,4-oxoisomerase Q6T1W8 FDTA_ANETH Aneurinibacillus thermoaerophilus 3 0.7335
Glutamate receptor 2 P19491 GRIA2_RAT Rattus norvegicus 2 0.7311
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 2 0.7304
Bromodomain-containing protein 2 P25440 BRD2_HUMAN Homo sapiens 3 0.7301
Genome polyprotein P26663 POLG_HCVBK Hepatitis C virus genotype 1b 3 0.7291
Nuclear receptor ROR-gamma P51449 RORG_HUMAN Homo sapiens 2 0.7282
Flavoredoxin Q72HI0 Q72HI0_THET2 Thermus thermophilus 2 0.7246
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7235
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 3 0.7230
Cytidine and deoxycytidylate deaminase zinc-binding region Q82Y41 Q82Y41_NITEU Nitrosomonas europaea 3 0.7222
Uncharacterized protein Q3F0V8 Q3F0V8_BACTI Bacillus thuringiensis serovar israelensis ATCC 35646 3 0.7217
Thymidylate synthase P00469 TYSY_LACCA Lacticaseibacillus casei 2 0.7209
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7201
Mitochondrial poly(A) polymerase F1NBW0 F1NBW0_CHICK Gallus gallus 2 0.7189
Cis-2,3-dihydrobiphenyl-2,3-diol dehydrogenase Q46381 BPHB_COMTE Comamonas testosteroni 3 0.7186
Tubulin alpha-1B chain P81947 TBA1B_BOVIN Bos taurus 3 0.7184
Estrogen receptor P03372 ESR1_HUMAN Homo sapiens 2 0.7176
Capsid protein Q9WBP8 Q9WBP8_9VIRU Adeno-associated virus - 1 2 0.7165
ATP-dependent molecular chaperone HSP82 P02829 HSP82_YEAST Saccharomyces cerevisiae 2 0.7150
Transcriptional regulator, PadR-like family A2RI36 A2RI36_LACLM Lactococcus lactis subsp. cremoris 2 0.7146
Serine/threonine-protein kinase pim-1 P11309 PIM1_HUMAN Homo sapiens 3 0.7140
Ribosomal small subunit pseudouridine synthase A P0AA43 RSUA_ECOLI Escherichia coli 3 0.7136
Casein kinase II subunit alpha P28523 CSK2A_MAIZE Zea mays 3 0.7131
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7099
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7099
Beta-2 adrenergic receptor P07550 ADRB2_HUMAN Homo sapiens 3 0.7093
Cytochrome P450 2C9 P11712 CP2C9_HUMAN Homo sapiens 2 0.7093
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 2 0.7093
Gastrotropin Q6IMW5 Q6IMW5_DANRE Danio rerio 2 0.7088
Bifunctional epoxide hydrolase 2 P34913 HYES_HUMAN Homo sapiens 2 0.7088
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7085
Aldo-keto reductase family 1 member B1 P15121 ALDR_HUMAN Homo sapiens 4 0.7084
3',5'-cyclic-AMP phosphodiesterase 4A P27815 PDE4A_HUMAN Homo sapiens 3 0.7084
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform P48736 PK3CG_HUMAN Homo sapiens 3 0.7082
Glucan 1,3-beta-glucosidase P29717 EXG1_CANAL Candida albicans 2 0.7078
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 3 0.7074
Alcohol dehydrogenase 1C P00326 ADH1G_HUMAN Homo sapiens 2 0.7069
Cyclin-dependent kinase 5 Q00535 CDK5_HUMAN Homo sapiens 3 0.7067
3-hydroxybenzoate 4-monooxygenase Q6SSJ6 MOBA_COMTE Comamonas testosteroni 2 0.7057
Neocarzinostatin P0A3R9 NCZS_STRCZ Streptomyces carzinostaticus 2 0.7052
Hematopoietic prostaglandin D synthase O60760 HPGDS_HUMAN Homo sapiens 2 0.7052
Glucan 1,3-beta-glucosidase P29717 EXG1_CANAL Candida albicans 2 0.7041
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7040
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7032
Albumin P02768 ALBU_HUMAN Homo sapiens 3 0.7031
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 2 0.7028
Serine/threonine-protein kinase pim-1 P11309 PIM1_HUMAN Homo sapiens 3 0.7010
Methionine aminopeptidase P0AE18 MAP1_ECOLI Escherichia coli 2 0.7005
Rhodopsin P02699 OPSD_BOVIN Bos taurus 2 0.7000

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