8-O-demethylmaritidine - Compound Card

8-O-demethylmaritidine

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8-O-demethylmaritidine

Structure
Zoomed Structure
  • Family: Plantae - Amaryllidaceae
  • Kingdom: Plantae
  • Class: Alkaloid
Canonical Smiles COc1cc2c(cc1O)CN1[C@@H]3[C@@]2(C=C[C@H](C3)O)CC1
InChI InChI=1S/C16H19NO3/c1-20-14-8-12-10(6-13(14)19)9-17-5-4-16(12)3-2-11(18)7-15(16)17/h2-3,6,8,11,15,18-19H,4-5,7,9H2,1H3/t11-,15+,16+/m1/s1
InChIKey TZTBAJFJEZRQCV-RLCCDNCMSA-N
Formula C16H19NO3
HBA 4
HBD 2
MW 273.33
Rotatable Bonds 1
TPSA 52.93
LogP 1.55
Number Rings 4
Number Aromatic Rings 1
Heavy Atom Count 20
Formal Charge 0
Fraction CSP3 0.5
Exact Mass 273.14
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Crinum calamistratum Amaryllidaceae Plantae 573715
2 Zephyranthes candida Amaryllidaceae Plantae 82257
3 Zephyranthes robusta Amaryllidaceae Plantae 1234388
4 Zephyranthes rosea Amaryllidaceae Plantae 146470

Showing of synonyms

  • Shawky E, El Sohafy S.M, et al. (2021). Profiling of acetylcholinesterase inhibitory alkaloids from some Crinum, Habranthus and Zephyranthes species by GC–MS combined with multivariate analyses and in silico studies.. Nat Prod Res, 2021, 35(5), 807-814.. [View] [PubMed]
Pubchem: 443683
Kegg Ligand: C12180
Chebi: 31027
Nmrshiftdb2: 60063522
Bindingdb: 50092611
CPRiL: 190662
Structure

SMILES: C1=CCCC(C123)N(CC2)Cc4c3cccc4

Level: 0

Mol. Weight: 273.33 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.85
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.810
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-1.9

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.430
Plasma Protein Binding
38.08
Steady State Volume of Distribution
-

Metabolism

Breast Cancer Resistance Protein
Non-Inhibitor
CYP 1A2 Inhibitor
Non-Inhibitor
CYP 1A2 Substrate
Non-Substrate
CYP 2C19 Inhibitor
Non-Inhibitor
CYP 2C19 Substrate
Substrate
CYP 2C9 Inhibitor
Non-Inhibitor
CYP 2C9 Substrate
Non-Substrate
CYP 2D6 Inhibitor
Inhibitor
CYP 2D6 Substrate
Substrate
CYP 3A4 Inhibitor
Non-Inhibitor
CYP 3A4 Substrate
Substrate
OATP1B1
Non-Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
12.410
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
1.030
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
-0.050
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
8.280
Micronucleos
Toxic
NR-AhR
Safe
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
-1.830
Rat (Acute)
2.860
Rat (Chronic Oral)
2.180
Fathead Minnow
4.050
Respiratory Disease
Toxic
Skin Sensitisation
Toxic
SR-ARE
Safe
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Safe

General Properties

Boiling Point
359.040
Hydration Free Energy
-9.070
Log(D) at pH=7.4
0.780
Log(P)
0.4
Log S
-1.43
Log(Vapor Pressure)
-6.83
Melting Point
216.75
pKa Acid
9.25
pKa Basic
7.41
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
rRNA N-glycosylase D9J2T9 D9J2T9_MOMBA Momordica balsamina 3 0.9284
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 3 0.8743
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8647
Acetylcholinesterase P04058 ACES_TETCF Tetronarce californica 3 0.8638
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 3 0.8625
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8575
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 3 0.8558
Phenylalanine-4-hydroxylase P00439 PH4H_HUMAN Homo sapiens 3 0.8558
Mitogen-activated protein kinase 1 P28482 MK01_HUMAN Homo sapiens 3 0.8513
NADPH dehydrogenase 1 Q02899 OYE1_SACPS Saccharomyces pastorianus 3 0.8385
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 3 0.8302
Pantothenate synthetase P9WIL5 PANC_MYCTU Mycobacterium tuberculosis 3 0.8172
Norsolorinic acid synthase Q12053 AFLC_ASPPU Aspergillus parasiticus 3 0.8166
Isoleucine--tRNA ligase P56690 SYI_THET8 Thermus thermophilus 3 0.8107
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.8096
Hypoxanthine phosphoribosyltransferase Q4DRC4 Q4DRC4_TRYCC Trypanosoma cruzi 3 0.8090
Tyrosine-protein kinase JAK3 P52333 JAK3_HUMAN Homo sapiens 3 0.8068
Dual specificity mitogen-activated protein kinase kinase 1 Q02750 MP2K1_HUMAN Homo sapiens 3 0.8037
Nitric oxide synthase oxygenase O34453 NOSO_BACSU Bacillus subtilis 4 0.8019
DNA gyrase subunit A P0AES5 GYRA_SHIFL Shigella flexneri 3 0.7914
Odorant binding protein ASP1 Q8WRW5 Q8WRW5_APIME Apis mellifera 3 0.7874
Sex hormone-binding globulin P04278 SHBG_HUMAN Homo sapiens 3 0.7872
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 3 0.7835
Tyrosine-protein kinase JAK1 P23458 JAK1_HUMAN Homo sapiens 4 0.7816
Quorum-sensing transcriptional activator Q8XBD0 Q8XBD0_ECO57 Escherichia coli O157:H7 3 0.7766
Potassium/sodium hyperpolarization-activated cyclic nucleotide-gated channel 4 Q9Y3Q4 HCN4_HUMAN Homo sapiens 4 0.7752
Acetylcholinesterase P04058 ACES_TETCF Tetronarce californica 3 0.7747
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7745
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.7708
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 2 0.7695
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 3 0.7668
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7656
Sulfotransferase 2B1 O00204 ST2B1_HUMAN Homo sapiens 3 0.7613
Sex hormone-binding globulin P04278 SHBG_HUMAN Homo sapiens 3 0.7562
Na(+):neurotransmitter symporter (Snf family) O67854 O67854_AQUAE Aquifex aeolicus 3 0.7525
Steroid 21-hydroxylase P08686 CP21A_HUMAN Homo sapiens 3 0.7523
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 3 0.7505
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7498
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7483
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7482
Cyclin-dependent kinase 9 P50750 CDK9_HUMAN Homo sapiens 3 0.7478
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 2 0.7455
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7443
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase Q05603 COBT_SALTY Salmonella typhimurium 3 0.7415
Sulfotransferase 2A1 Q06520 ST2A1_HUMAN Homo sapiens 3 0.7393
3-alpha-hydroxysteroid dehydrogenase P23457 DIDH_RAT Rattus norvegicus 3 0.7352
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.7344
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.7322
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7301
Peptidyl-prolyl cis-trans isomerase FKBP1A P62942 FKB1A_HUMAN Homo sapiens 3 0.7285
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7268
HLA class I histocompatibility antigen, B alpha chain P01889 HLAB_HUMAN Homo sapiens 3 0.7230
Type II methyltransferase M.TaqI P14385 MTTA_THEAQ Thermus aquaticus 3 0.7226
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7211
Estrogen receptor P03372 ESR1_HUMAN Homo sapiens 3 0.7182
17-beta-hydroxysteroid dehydrogenase type 1 P14061 DHB1_HUMAN Homo sapiens 3 0.7142
Aldo-keto reductase family 1 member C1 Q04828 AK1C1_HUMAN Homo sapiens 2 0.7129
3'-5' exoribonuclease Rv2179c P9WJ73 EXRBN_MYCTU Mycobacterium tuberculosis 2 0.7128
Probable NDP-rhamnosyltransferase Q9ALM8 Q9ALM8_SACSN Saccharopolyspora spinosa 2 0.7124
Histone-lysine N-methyltransferase EHMT1 Q9H9B1 EHMT1_HUMAN Homo sapiens 3 0.7114
Phenylalanine-4-hydroxylase P00439 PH4H_HUMAN Homo sapiens 3 0.7102
Hypoxanthine-guanine phosphoribosyltransferase P00492 HPRT_HUMAN Homo sapiens 3 0.7096
Beta-galactoside-specific lectin 4 Q6ITZ3 ML4_VISAL Viscum album 2 0.7094
Tyrosine-protein kinase JAK1 P23458 JAK1_HUMAN Homo sapiens 3 0.7081
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7066
Guanylate kinase P15454 KGUA_YEAST Saccharomyces cerevisiae 3 0.7062
Hypoxanthine-guanine phosphoribosyltransferase P00492 HPRT_HUMAN Homo sapiens 3 0.7046
Phosphatidylinositol 5-phosphate 4-kinase type-2 beta P78356 PI42B_HUMAN Homo sapiens 3 0.7042
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7017
5'-methylthioadenosine/S-adenosylhomocysteine nucleosidase P0AF12 MTNN_ECOLI Escherichia coli 2 0.7012
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 2 0.7011

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