Mayselignoside - Compound Card

Mayselignoside

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Mayselignoside

Structure
Zoomed Structure
  • Family: Plantae - Celastraceae
  • Kingdom: Plantae
  • Class: Lignan
    • Subclass: Neolignan Glycoside
Canonical Smiles OC[C@H]1c2cc(CCCO[C@H]3OC[C@@H]([C@H]([C@@H]3O)O)O)cc(c2O[C@@H]1c1ccc(c(c1)OC)O)OC
InChI InChI=1S/C25H32O10/c1-31-19-10-14(5-6-17(19)27)23-16(11-26)15-8-13(9-20(32-2)24(15)35-23)4-3-7-33-25-22(30)21(29)18(28)12-34-25/h5-6,8-10,16,18,21-23,25-30H,3-4,7,11-12H2,1-2H3/t16-,18-,21+,22-,23+,25-/m0/s1
InChIKey BICDRYOIBXRFSE-QYUKQCCASA-N
Formula C25H32O10
HBA 10
HBD 5
MW 492.52
Rotatable Bonds 9
TPSA 147.3
LogP 1.01
Number Rings 4
Number Aromatic Rings 2
Heavy Atom Count 35
Formal Charge 0
Fraction CSP3 0.52
Exact Mass 492.2
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Maytenus senegalensis Celastraceae Plantae 256095

Showing of synonyms

  • Okoye FB, Agbo MO, et al. (2014). New neolignan glycoside and an unusual benzoyl malic acid derivative from Maytenus senegalensis leaves. Natural Product Research,2014,29,109-115. [View]

No compound-protein relationship available.

Structure

SMILES: O1CCCCC1OCCCc(c2)ccc(c23)OC(C3)c4ccccc4

Level: 2

Mol. Weight: 492.52 g/mol

Structure

SMILES: O1CCCCC1OCCCc(c2)ccc(c23)OCC3

Level: 1

Mol. Weight: 492.52 g/mol

Structure

SMILES: c1cccc(c12)OC(C2)c3ccccc3

Level: 1

Mol. Weight: 492.52 g/mol

Structure

SMILES: C1COc(c12)cccc2

Level: 0

Mol. Weight: 492.52 g/mol

Structure

SMILES: C1CCOCC1

Level: 0

Mol. Weight: 492.52 g/mol

Structure

SMILES: c1ccccc1

Level: 0

Mol. Weight: 492.52 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-6.38
Human Oral Bioavailability 20%
Non-Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.970
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Inhibitor
P-Glycoprotein Substrate
Substrate
Skin Permeability
-2.14

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
0.990
Plasma Protein Binding
83.48
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
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
Non-Inhibitor
CYP 3A4 Substrate
Substrate
OATP1B1
Non-Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
11.270
Organic Cation Transporter 2
Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-1.240
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.460
Liver Injury II
Toxic
hERG Blockers
Toxic
Daphnia Maga
4.880
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
-471.400
Rat (Acute)
2.390
Rat (Chronic Oral)
3.500
Fathead Minnow
4.430
Respiratory Disease
Safe
Skin Sensitisation
Safe
SR-ARE
Safe
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Safe

General Properties

Boiling Point
513.590
Hydration Free Energy
-3.010
Log(D) at pH=7.4
1.800
Log(P)
-0.46
Log S
-3.74
Log(Vapor Pressure)
-10.98
Melting Point
183.27
pKa Acid
7.3
pKa Basic
2.57
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.9475
Bifunctional epoxide hydrolase 2 P34913 HYES_HUMAN Homo sapiens 3 0.9403
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 3 0.9302
D-aminoacyl-tRNA deacylase Q8IIS0 DTD_PLAF7 Plasmodium falciparum 3 0.9171
Xylose isomerase P24300 XYLA_STRRU Streptomyces rubiginosus 3 0.9108
Mycocyclosin synthase P9WPP7 CP121_MYCTU Mycobacterium tuberculosis 3 0.9100
Flavoredoxin Q72HI0 Q72HI0_THET2 Thermus thermophilus 3 0.9069
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.9047
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 3 0.8962
Thymidine phosphorylase Q7CP66 TYPH_SALTY Salmonella typhimurium 3 0.8958
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 3 0.8897
Mycocyclosin synthase P9WPP7 CP121_MYCTU Mycobacterium tuberculosis 4 0.8823
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 3 0.8798
Cathepsin S P25774 CATS_HUMAN Homo sapiens 3 0.8687
Stromelysin-1 P08254 MMP3_HUMAN Homo sapiens 3 0.8624
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 3 0.8570
Steroid C26-monooxygenase P9WPP1 CP125_MYCTU Mycobacterium tuberculosis 3 0.8549
Mitogen-activated protein kinase 1 P28482 MK01_HUMAN Homo sapiens 3 0.8477
Rhodopsin kinase GRK1 P28327 GRK1_BOVIN Bos taurus 3 0.8467
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.8464
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.8374
Pantothenate synthetase P9WIL5 PANC_MYCTU Mycobacterium tuberculosis 3 0.8320
Streptogramin A acetyltransferase P50870 VATD_ENTFC Enterococcus faecium 3 0.8310
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.8298
rRNA N-glycosylase D9J2T9 D9J2T9_MOMBA Momordica balsamina 3 0.8282
Protein ppBat Q8A8A4 Q8A8A4_BACTN Bacteroides thetaiotaomicron VPI-5482 3 0.8255
Purine nucleoside phosphorylase P00491 PNPH_HUMAN Homo sapiens 3 0.8253
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.8245
Phenylalanine-4-hydroxylase P00439 PH4H_HUMAN Homo sapiens 3 0.8206
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.8200
Tetracycline repressor protein class B from transposon Tn10 P04483 TETR2_ECOLX Escherichia coli 3 0.8186
MAP kinase-activated protein kinase 2 P49137 MAPK2_HUMAN Homo sapiens 3 0.8176
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 3 0.8141
Mycocyclosin synthase P9WPP7 CP121_MYCTU Mycobacterium tuberculosis 3 0.8104
Hypoxanthine phosphoribosyltransferase Q4DRC4 Q4DRC4_TRYCC Trypanosoma cruzi 3 0.8084
Focal adhesion kinase 1 Q05397 FAK1_HUMAN Homo sapiens 4 0.8081
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.8067
GCN5-related N-acetyltransferase B1YEL6 B1YEL6_EXIS2 Exiguobacterium sibiricum 3 0.8052
GCN5-related N-acetyltransferase B1YEL6 B1YEL6_EXIS2 Exiguobacterium sibiricum 3 0.8038
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.8038
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8025
Serine/threonine-protein kinase 24 Q9Y6E0 STK24_HUMAN Homo sapiens 3 0.8018
Abscisic acid receptor PYL2 O80992 PYL2_ARATH Arabidopsis thaliana 3 0.7996
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7972
Abscisic acid receptor PYR1 O49686 PYR1_ARATH Arabidopsis thaliana 3 0.7970
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.7935
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 3 0.7914
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7909
Gag-Pol polyprotein P05896 POL_SIVM1 Simian immunodeficiency virus 4 0.7905
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7891
Dual specificity mitogen-activated protein kinase kinase 1 Q02750 MP2K1_HUMAN Homo sapiens 3 0.7867
DNA gyrase subunit A P0AES5 GYRA_SHIFL Shigella flexneri 3 0.7852
Cytochrome P450 1A1 P04798 CP1A1_HUMAN Homo sapiens 3 0.7848
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7814
Mitogen-activated protein kinase 14 Q16539 MK14_HUMAN Homo sapiens 3 0.7759
Potassium/sodium hyperpolarization-activated cyclic nucleotide-gated channel 4 Q9Y3Q4 HCN4_HUMAN Homo sapiens 4 0.7758
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.7743
Streptavidin P22629 SAV_STRAV Streptomyces avidinii 3 0.7682
Tau-tubulin kinase 1 Q5TCY1 TTBK1_HUMAN Homo sapiens 4 0.7668
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.7642
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7633
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7607
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7588
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7568
Disks large homolog 1 Q12959 DLG1_HUMAN Homo sapiens 4 0.7567
Dual specificity mitogen-activated protein kinase kinase 1 Q02750 MP2K1_HUMAN Homo sapiens 3 0.7565
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 3 0.7564
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7521
Riboflavin synthase P0AFU8 RISA_ECOLI Escherichia coli 3 0.7516
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.7515
cGMP-dependent 3',5'-cyclic phosphodiesterase O00408 PDE2A_HUMAN Homo sapiens 3 0.7507
Thymidylate synthase P0A886 TYSY_ECO57 Escherichia coli O157:H7 3 0.7506
Proliferating cell nuclear antigen P12004 PCNA_HUMAN Homo sapiens 3 0.7504
Phytohormone-binding protein CSBP A0A1S3THR8 PHBP_VIGRR Vigna radiata var. radiata 3 0.7494
Vascular endothelial growth factor receptor 2 P35968 VGFR2_HUMAN Homo sapiens 3 0.7492
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7468
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 2 0.7465
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7440
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7429
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.7422
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7420
Gag-Pol polyprotein P03367 POL_HV1BR Human immunodeficiency virus type 1 group M subtype B 3 0.7389
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7356
Bromodomain-containing protein 2 P25440 BRD2_HUMAN Homo sapiens 3 0.7349
Gag-Pol polyprotein P12497 POL_HV1N5 Human immunodeficiency virus type 1 group M subtype B 2 0.7349
HTH-type transcriptional regulator QacR P0A0N4 QACR_STAAU Staphylococcus aureus 2 0.7346
Lysosomal acid glucosylceramidase P04062 GLCM_HUMAN Homo sapiens 3 0.7330
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7325
APH(2'')-Id O68183 O68183_ENTCA Enterococcus casseliflavus 3 0.7323
Lethal factor P15917 LEF_BACAN Bacillus anthracis 3 0.7321
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7321
Pancreatic alpha-amylase P04746 AMYP_HUMAN Homo sapiens 2 0.7321
Protein mono-ADP-ribosyltransferase PARP15 Q460N3 PAR15_HUMAN Homo sapiens 3 0.7315
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7315
Polymerase acidic protein C3W5S0 C3W5S0_I09A0 Influenza A virus 2 0.7310
Histone-lysine N-methyltransferase EHMT1 Q9H9B1 EHMT1_HUMAN Homo sapiens 3 0.7308
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7305
Beta-lactamase Q9L5C8 Q9L5C8_ECOLX Escherichia coli 3 0.7299
Endothiapepsin P11838 CARP_CRYPA Cryphonectria parasitica 3 0.7297
Catechol O-methyltransferase P22734 COMT_RAT Rattus norvegicus 3 0.7294
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7293
Methylmalonyl-CoA decarboxylase P52045 SCPB_ECOLI Escherichia coli 3 0.7292
ATP-dependent protease subunit HslV P0A7B8 HSLV_ECOLI Escherichia coli 3 0.7285
Phosphatidylinositol 5-phosphate 4-kinase type-2 beta P78356 PI42B_HUMAN Homo sapiens 3 0.7282
Aldo-keto reductase family 1 member B1 P15121 ALDR_HUMAN Homo sapiens 2 0.7277
Chalcone--flavanone isomerase 1 P28012 CFI1_MEDSA Medicago sativa 3 0.7275
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7268
Cytosolic purine 5'-nucleotidase P49902 5NTC_HUMAN Homo sapiens 2 0.7264
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7248
Casein kinase I isoform gamma-3 Q9Y6M4 KC1G3_HUMAN Homo sapiens 3 0.7242
Ephrin type-B receptor 2 P54763 EPHB2_MOUSE Mus musculus 2 0.7241
Beta-galactoside-specific lectin 4 Q6ITZ3 ML4_VISAL Viscum album 2 0.7230
Nuclear receptor subfamily 4immunitygroup A member 1 P22736 NR4A1_HUMAN Homo sapiens 3 0.7222
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7221
2',3'-cyclic-nucleotide 3'-phosphodiesterase P16330 CN37_MOUSE Mus musculus 3 0.7218
APH(2'')-Id O68183 O68183_ENTCA Enterococcus casseliflavus 3 0.7217
Inorganic pyrophosphatase Q3JUV5 Q3JUV5_BURP1 Burkholderia pseudomallei 2 0.7212
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7204
Capsid protein Q9WBP8 Q9WBP8_9VIRU Adeno-associated virus - 1 2 0.7203
Lactoperoxidase A0A452E9Y6 PERL_CAPHI Capra hircus 3 0.7189
16S rRNA (guanine(1405)-N(7))-methyltransferase Q763K9 Q763K9_ECOLX Escherichia coli 3 0.7187
Beta-glucuronidase P05804 BGLR_ECOLI Escherichia coli 3 0.7182
Non-receptor tyrosine-protein kinase TYK2 P29597 TYK2_HUMAN Homo sapiens 3 0.7169
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 2 0.7167
Glutathione S-transferase P P09211 GSTP1_HUMAN Homo sapiens 2 0.7160
Histone-lysine N-methyltransferase EHMT2 Q96KQ7 EHMT2_HUMAN Homo sapiens 3 0.7157
Homoserine dehydrogenase P31116 DHOM_YEAST Saccharomyces cerevisiae 3 0.7145
N-terminal acetyltransferase A complex subunit NAT1 P12945 NAT1_YEAST Saccharomyces cerevisiae 2 0.7145
Thymidylate synthase P0A884 TYSY_ECOLI Escherichia coli 3 0.7143
11-beta-hydroxysteroid dehydrogenase 1 P28845 DHI1_HUMAN Homo sapiens 3 0.7136
Nitric oxide synthase oxygenase O34453 NOSO_BACSU Bacillus subtilis 3 0.7135
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7130
Histone-lysine N-methyltransferase, H3 lysine-9 specific SUVH4 Q8GZB6 SUVH4_ARATH Arabidopsis thaliana 3 0.7125
Adenylate cyclase type 5 P30803 ADCY5_CANLF Canis lupus familiaris 3 0.7115
L-lactate dehydrogenase A chain P04642 LDHA_RAT Rattus norvegicus 2 0.7114
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7113
Histone-lysine N-methyltransferase 2A Q03164 KMT2A_HUMAN Homo sapiens 3 0.7109
UDP-N-acetylmuramoyl-tripeptide--D-alanyl-D-alanine ligase Q8DNV6 Q8DNV6_STRR6 Streptococcus pneumoniae 3 0.7109
Ethylene receptor 1 P49333 ETR1_ARATH Arabidopsis thaliana 3 0.7108
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7106
Threonine--tRNA ligase P0A8M3 SYT_ECOLI Escherichia coli 3 0.7102
dTDP-4-dehydrorhamnose 3,5-epimerase A0A6L7H6N0 A0A1S0QLH9_BACAN Bacillus anthracis 3 0.7101
Valacyclovir hydrolase Q86WA6 BPHL_HUMAN Homo sapiens 3 0.7101
ActVA 6 protein Q53908 Q53908_STRCH Streptomyces coelicolor 3 0.7100
Cytidine and deoxycytidylate deaminase zinc-binding region Q82Y41 Q82Y41_NITEU Nitrosomonas europaea 2 0.7095
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.7082
Mitogen-activated protein kinase FUS3 P16892 FUS3_YEAST Saccharomyces cerevisiae 4 0.7078
Catechol O-methyltransferase P22734 COMT_RAT Rattus norvegicus 3 0.7077
Hypoxanthine-guanine phosphoribosyltransferase P00492 HPRT_HUMAN Homo sapiens 3 0.7044
DNA polymerase III subunit epsilon P03007 DPO3E_ECOLI Escherichia coli 3 0.7043
Serine/threonine-protein kinase SKY1 Q03656 SKY1_YEAST Saccharomyces cerevisiae 2 0.7042
ADP compounds hydrolase NudE P45799 NUDE_ECOLI Escherichia coli 2 0.7042
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7040
Dual specificity mitogen-activated protein kinase kinase 1 Q02750 MP2K1_HUMAN Homo sapiens 3 0.7037
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7029
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 2 0.7029
Non-receptor tyrosine-protein kinase TYK2 P29597 TYK2_HUMAN Homo sapiens 3 0.7027
Actin, alpha skeletal muscle P68135 ACTS_RABIT Oryctolagus cuniculus 3 0.7025
Putative ketoacyl reductase P16544 ACT3_STRCO Streptomyces coelicolor / M145) 3 0.7018
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7017
Pheromone-binding protein ASP1 Q9U9J6 Q9U9J6_APIME Apis mellifera 2 0.7013
Dipeptidyl peptidase 4 P27487 DPP4_HUMAN Homo sapiens 3 0.7001

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