Demethylmoracin I - Compound Card

Demethylmoracin I

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Demethylmoracin I

Structure
Zoomed Structure
  • Family: Plantae - Moraceae
  • Kingdom: Plantae
  • Class: Phenolic
    • Subclass: Benzofuran
Canonical Smiles CC(=CCc1c(O)cc(cc1c1oc2c(c1)ccc(c2)O)O)C
InChI InChI=1S/C19H18O4/c1-11(2)3-6-15-16(8-14(21)9-17(15)22)19-7-12-4-5-13(20)10-18(12)23-19/h3-5,7-10,20-22H,6H2,1-2H3
InChIKey KDDIWXQFRQYXCG-UHFFFAOYSA-N
Formula C19H18O4
HBA 4
HBD 3
MW 310.35
Rotatable Bonds 3
TPSA 73.83
LogP 4.73
Number Rings 3
Number Aromatic Rings 3
Heavy Atom Count 23
Formal Charge 0
Fraction CSP3 0.16
Exact Mass 310.12
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Morus mesozygia Moraceae Plantae 3054370

Showing of synonyms

  • Kapche GD, Amadou D, et al. (2011). Hepatoprotective and antioxidant arylbenzofurans and flavonoids from the twigs of Morus mesozygia.. Planta medica,2011, 77(10), 1044-1047. [View] [PubMed]
Pubchem: 641375
Nmrshiftdb2: 10025014
Bindingdb: 50250980

No compound-protein relationship available.

Structure

SMILES: c1cccc(c12)oc(c2)-c3ccccc3

Level: 1

Mol. Weight: 310.35 g/mol

Structure

SMILES: c1coc(c12)cccc2

Level: 0

Mol. Weight: 310.35 g/mol

Structure

SMILES: c1ccccc1

Level: 0

Mol. Weight: 310.35 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.87
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.76
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-1.26

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
0.86
Plasma Protein Binding
71.58
Steady State Volume of Distribution
-

Metabolism

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

Excretion

Clearance
2.79
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Safe
Bioconcentration Factor
1.94
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Toxic
Eye Corrosion
Safe
Eye Irritation
Toxic
Maximum Tolerated Dose
0.68
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
5.78
Micronucleos
Toxic
NR-AhR
Toxic
NR-AR
Safe
NR-AR-LBD
Safe
NR-Aromatase
Safe
NR-ER
Toxic
NR-ER-LBD
Safe
NR-GR
Toxic
NR-PPAR-gamma
Safe
NR-TR
Safe
T. Pyriformis
3.36
Rat (Acute)
1.87
Rat (Chronic Oral)
2.79
Fathead Minnow
4.94
Respiratory Disease
Toxic
Skin Sensitisation
Toxic
SR-ARE
Toxic
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Toxic
SR-p53
Toxic

General Properties

Boiling Point
436.55
Hydration Free Energy
-11.51
Log(D) at pH=7.4
3.81
Log(P)
4.74
Log S
-5.09
Log(Vapor Pressure)
-8.4
Melting Point
227.61
pKa Acid
8.64
pKa Basic
7.28
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
NADH:flavin oxidoreductase Sye1 Q8EEC8 Q8EEC8_SHEON Shewanella oneidensis 3 0.9374
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.9302
tyrosine--tRNA ligase Q4QFJ7 Q4QFJ7_LEIMA Leishmania major 4 0.9226
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 3 0.9195
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.9149
Multidrug-efflux transporter 1 regulator P39075 BMRR_BACSU Bacillus subtilis 3 0.9018
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.8985
Cathepsin S P25774 CATS_HUMAN Homo sapiens 3 0.8976
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.8919
GTPase KRas P01116 RASK_HUMAN Homo sapiens 3 0.8844
Nodulin-13 P93330 NOD13_MEDTR Medicago truncatula 3 0.8819
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.8740
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform O02697 PK3CG_PIG Sus scrofa 3 0.8726
17-beta-hydroxysteroid dehydrogenase type 1 P14061 DHB1_HUMAN Homo sapiens 4 0.8720
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 3 0.8672
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 3 0.8667
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 3 0.8627
17-beta-hydroxysteroid dehydrogenase type 1 P14061 DHB1_HUMAN Homo sapiens 4 0.8623
3-ketosteroid dehydrogenase Q9RA02 Q9RA02_RHOER Rhodococcus erythropolis 3 0.8565
Mitogen-activated protein kinase 1 P28482 MK01_HUMAN Homo sapiens 3 0.8492
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 3 0.8490
Carbonyl reductase [NADPH] 1 P16152 CBR1_HUMAN Homo sapiens 3 0.8486
cGMP-dependent 3',5'-cyclic phosphodiesterase O00408 PDE2A_HUMAN Homo sapiens 3 0.8473
Metapyrocatechase Q7WYF5 Q7WYF5_9PSED Pseudomonas alkylphenolica 3 0.8460
Peroxisome proliferator-activated receptor gamma P37231 PPARG_HUMAN Homo sapiens 4 0.8432
Dihydrofolate reductase P00378 DYR_CHICK Gallus gallus 3 0.8427
Carminomycin 4-O-methyltransferase DnrK Q06528 DNRK_STRPE Streptomyces peucetius 3 0.8398
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.8369
Histone deacetylase 4 P56524 HDAC4_HUMAN Homo sapiens 3 0.8306
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 4 0.8300
Leucoanthocyanidin dioxygenase Q96323 LDOX_ARATH Arabidopsis thaliana 4 0.8244
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 4 0.8235
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.8210
Estrogen receptor P03372 ESR1_HUMAN Homo sapiens 4 0.8187
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase Q9TQS6 DHDH_MACFA Macaca fascicularis 3 0.8167
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.8145
cAMP-dependent protein kinase type I-alpha regulatory subunit P00514 KAP0_BOVIN Bos taurus 3 0.8138
Peptidyl-prolyl cis-trans isomerase FKBP5 Q13451 FKBP5_HUMAN Homo sapiens 3 0.8123
Cytochrome P450 monooxygenase Q5YNS8 Q5YNS8_NOCFA Nocardia farcinica 3 0.8118
Peroxisome proliferator-activated receptor gamma P37231 PPARG_HUMAN Homo sapiens 3 0.8066
HTH-type transcriptional regulator TtgR Q9AIU0 TTGR_PSEPT Pseudomonas putida 3 0.8048
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.8034
Death-associated protein kinase 1 P53355 DAPK1_HUMAN Homo sapiens 4 0.8026
Fatty acid-binding protein, liver P80226 FABPL_CHICK Gallus gallus 3 0.7998
Phospholipase A2, major isoenzyme P00592 PA21B_PIG Sus scrofa 3 0.7982
Carbonyl reductase [NADPH] 1 P16152 CBR1_HUMAN Homo sapiens 3 0.7981
Chitinase Q54276 Q54276_SERMA Serratia marcescens 3 0.7964
Bromodomain-containing protein 2 P25440 BRD2_HUMAN Homo sapiens 3 0.7959
Serine/threonine-protein kinase pim-1 P11309 PIM1_HUMAN Homo sapiens 3 0.7917
Tyrosine-protein kinase JAK3 P52333 JAK3_HUMAN Homo sapiens 3 0.7890
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7889
Mycocyclosin synthase P9WPP7 CP121_MYCTU Mycobacterium tuberculosis 3 0.7876
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7863
Soluble cytochrome b562 P0ABE7 C562_ECOLX Escherichia coli 3 0.7854
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 3 0.7853
Heat shock protein 75 kDa, mitochondrial Q12931 TRAP1_HUMAN Homo sapiens 4 0.7817
Purine nucleoside phosphorylase DeoD-type P0ABP8 DEOD_ECOLI Escherichia coli 3 0.7784
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7777
Phosphodiesterase Q8WQX9 Q8WQX9_9TRYP Trypanosoma brucei 3 0.7757
Serine/threonine-protein kinase 24 Q9Y6E0 STK24_HUMAN Homo sapiens 3 0.7745
Cytohesin-2 Q99418 CYH2_HUMAN Homo sapiens 3 0.7736
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.7734
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7734
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7688
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7682
Cytochrome P450 2B4 P00178 CP2B4_RABIT Oryctolagus cuniculus 3 0.7672
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.7667
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.7637
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7629
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 2 0.7627
Phosphatidylinositol 3-kinase catalytic subunit type 3 Q8NEB9 PK3C3_HUMAN Homo sapiens 4 0.7601
Progesterone receptor P06401 PRGR_HUMAN Homo sapiens 3 0.7596
Glucan 1,3-beta-glucosidase P29717 EXG1_CANAL Candida albicans 3 0.7582
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7574
DNA gyrase subunit B Q839Z1 GYRB_ENTFA Enterococcus faecalis 3 0.7550
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 4 0.7543
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 2 0.7538
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7494
Flavin-dependent thymidylate synthase Q9WYT0 THYX_THEMA Thermotoga maritima 3 0.7481
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7479
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7478
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 3 0.7474
Glutathione S-transferase F2 P46422 GSTF2_ARATH Arabidopsis thaliana 3 0.7469
Serine/threonine-protein kinase pim-1 P11309 PIM1_HUMAN Homo sapiens 3 0.7451
Genome polyprotein O92972 POLG_HCVJ4 Hepatitis C virus genotype 1b 3 0.7442
HLA class I histocompatibility antigen, B alpha chain P01889 HLAB_HUMAN Homo sapiens 3 0.7440
Gag-Pol polyprotein P03367 POL_HV1BR Human immunodeficiency virus type 1 group M subtype B 3 0.7434
Chalcone--flavanone isomerase 1 P28012 CFI1_MEDSA Medicago sativa 4 0.7430
Dihydrofolate reductase P22906 DYR_CANAX Candida albicans 3 0.7424
HTH-type transcriptional regulator QacR P0A0N3 QACR_STAAM Staphylococcus aureus 3 0.7419
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 3 0.7400
Serine/threonine-protein kinase 24 Q9Y6E0 STK24_HUMAN Homo sapiens 3 0.7395
Sterol 14alpha-demethylase P9WPP9 CP51_MYCTU Mycobacterium tuberculosis 3 0.7389
Rhodopsin kinase GRK1 P28327 GRK1_BOVIN Bos taurus 3 0.7385
Beta-secretase 2 Q9Y5Z0 BACE2_HUMAN Homo sapiens 2 0.7384
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7373
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7365
HTH-type transcriptional regulator QacR P0A0N4 QACR_STAAU Staphylococcus aureus 3 0.7360
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.7354
Adenylate cyclase 2 A0A2U2H3Y1 A0A384LKY8_YERPE Yersinia pestis 3 0.7341
Glucose-1-phosphate thymidylyltransferase Q9HU22 Q9HU22_PSEAE Pseudomonas aeruginosa 3 0.7330
Chloramphenicol acetyltransferase P62577 CAT_ECOLX Escherichia coli 3 0.7325
Glutamate receptor 2 P19491 GRIA2_RAT Rattus norvegicus 3 0.7319
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.7314
Cathepsin S P25774 CATS_HUMAN Homo sapiens 3 0.7314
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 3 0.7312
Acetylcholinesterase P22303 ACES_HUMAN Homo sapiens 3 0.7295
Dihydrofolate reductase P0ABQ4 DYR_ECOLI Escherichia coli 3 0.7267
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 3 0.7264
Cytochrome P450 2E1 P05181 CP2E1_HUMAN Homo sapiens 3 0.7264
HTH-type transcriptional regulator TtgR Q9AIU0 TTGR_PSEPT Pseudomonas putida 3 0.7253
Angiotensin-converting enzyme 2 Q9BYF1 ACE2_HUMAN Homo sapiens 2 0.7241
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7217
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7216
17-beta-hydroxysteroid dehydrogenase type 1 P14061 DHB1_HUMAN Homo sapiens 3 0.7211
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7210
Protein UshA P07024 USHA_ECOLI Escherichia coli 3 0.7198
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7170
Thymidylate synthase P00469 TYSY_LACCA Lacticaseibacillus casei 2 0.7158
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 3 0.7156
Lethal(3)malignant brain tumor-like protein 1 Q9Y468 LMBL1_HUMAN Homo sapiens 3 0.7153
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7151
Mitochondrial poly(A) polymerase F1NBW0 F1NBW0_CHICK Gallus gallus 2 0.7148
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7143
Sulfotransferase 2A1 Q06520 ST2A1_HUMAN Homo sapiens 3 0.7141
Methionine aminopeptidase 2 P9WK19 MAP12_MYCTU Mycobacterium tuberculosis 3 0.7137
Peptidyl-prolyl cis-trans isomerase FKBP5 Q13451 FKBP5_HUMAN Homo sapiens 3 0.7136
Phosphoglycerate kinase 1 P00558 PGK1_HUMAN Homo sapiens 4 0.7136
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7133
Actin, alpha skeletal muscle P68135 ACTS_RABIT Oryctolagus cuniculus 3 0.7104
Kinesin-like protein KIF11 P52732 KIF11_HUMAN Homo sapiens 3 0.7098
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7092
Leucoanthocyanidin dioxygenase Q96323 LDOX_ARATH Arabidopsis thaliana 4 0.7082
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7081
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 2 0.7078
Heat shock protein HSP 90-beta P08238 HS90B_HUMAN Homo sapiens 3 0.7062
Oxygenase Q194P4 Q194P4_STRAA Streptomyces argillaceus 3 0.7054
Leucoanthocyanidin dioxygenase Q96323 LDOX_ARATH Arabidopsis thaliana 4 0.7050
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7043
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.7038
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7019
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.7018
Isoleucine--tRNA ligase P56690 SYI_THET8 Thermus thermophilus 3 0.7016
Ribosomal small subunit pseudouridine synthase A P0AA43 RSUA_ECOLI Escherichia coli 3 0.7014
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7014
Serine/threonine-protein kinase 24 Q9Y6E0 STK24_HUMAN Homo sapiens 2 0.7010
Streptavidin P22629 SAV_STRAV Streptomyces avidinii 3 0.7007
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 3 0.7004

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