6-methoxydiphyllin - Compound Card

6-methoxydiphyllin

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6-methoxydiphyllin

Structure
Zoomed Structure
  • Family: Animalia - Apidae
  • Kingdom: Animalia
  • Class: Phenolic
    • Subclass: Lignan
Canonical Smiles COc1cc2[C@@H](c3ccc4c(c3)OCO4)[C@H]3C(=O)OCC3C(c2c(c1OC)OC)O
InChI InChI=1S/C22H22O8/c1-25-15-7-11-16(10-4-5-13-14(6-10)30-9-29-13)17-12(8-28-22(17)24)19(23)18(11)21(27-3)20(15)26-2/h4-7,12,16-17,19,23H,8-9H2,1-3H3/t12?,16-,17+,19?/m1/s1
InChIKey YDSHUGJNIUQDAY-OKROVLOASA-N
Formula C22H22O8
HBA 8
HBD 1
MW 414.41
Rotatable Bonds 4
TPSA 92.68
LogP 2.41
Number Rings 5
Number Aromatic Rings 2
Heavy Atom Count 30
Formal Charge 0
Fraction CSP3 0.41
Exact Mass 414.13
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Apis species Apidae Animalia 7459

Showing of synonyms

  • Petrova A, Popova M, et al. (2010). New biologically active compounds from Kenyan propolis.. Fitoterapia,2010,81(6),509-514. [View] [PubMed]

No compound-protein relationship available.

Structure

SMILES: O1COc(c12)ccc(c2)C3c(cccc4)c4CC(C35)COC5=O

Level: 1

Mol. Weight: 414.41 g/mol

Structure

SMILES: O=C1OCC(C12)Cc3c(C2)cccc3

Level: 0

Mol. Weight: 414.41 g/mol

Structure

SMILES: O1COc(c12)cccc2

Level: 0

Mol. Weight: 414.41 g/mol

Antibacterial

Absorption

Caco-2 (logPapp)
-5.02
Human Oral Bioavailability 20%
Non-Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.700
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.4

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
1.020
Plasma Protein Binding
64.44
Steady State Volume of Distribution
-

Metabolism

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

Excretion

Clearance
13.400
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
1.530
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.180
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
6.610
Micronucleos
Toxic
NR-AhR
Toxic
NR-AR
Safe
NR-AR-LBD
Safe
NR-Aromatase
Safe
NR-ER
Safe
NR-ER-LBD
Safe
NR-GR
Toxic
NR-PPAR-gamma
Safe
NR-TR
Toxic
T. Pyriformis
-68.890
Rat (Acute)
2.660
Rat (Chronic Oral)
2.310
Fathead Minnow
5.210
Respiratory Disease
Toxic
Skin Sensitisation
Safe
SR-ARE
Safe
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Toxic
SR-p53
Safe

General Properties

Boiling Point
468.740
Hydration Free Energy
-3.130
Log(D) at pH=7.4
2.230
Log(P)
1.79
Log S
-3.5
Log(Vapor Pressure)
-8.79
Melting Point
181.08
pKa Acid
8.71
pKa Basic
0.54
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8763
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8763
Streptogramin A acetyltransferase P50870 VATD_ENTFC Enterococcus faecium 3 0.8762
Streptogramin A acetyltransferase P50870 VATD_ENTFC Enterococcus faecium 3 0.8762
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase Q05603 COBT_SALTY Salmonella typhimurium 3 0.8551
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase Q05603 COBT_SALTY Salmonella typhimurium 3 0.8551
Genome polyprotein O92972 POLG_HCVJ4 Hepatitis C virus genotype 1b 4 0.8544
Genome polyprotein O92972 POLG_HCVJ4 Hepatitis C virus genotype 1b 4 0.8544
Glucan 1,3-beta-glucosidase P29717 EXG1_CANAL Candida albicans 3 0.8360
Glucan 1,3-beta-glucosidase P29717 EXG1_CANAL Candida albicans 3 0.8360
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8322
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8322
Aminoglycoside 3'-phosphotransferase AphA1-IAB B0VD92 B0VD92_ACIBY Acinetobacter baumannii 4 0.8254
Aminoglycoside 3'-phosphotransferase AphA1-IAB B0VD92 B0VD92_ACIBY Acinetobacter baumannii 4 0.8254
cGMP-specific 3',5'-cyclic phosphodiesterase O76074 PDE5A_HUMAN Homo sapiens 3 0.8199
cGMP-specific 3',5'-cyclic phosphodiesterase O76074 PDE5A_HUMAN Homo sapiens 3 0.8199
Serine/threonine-protein kinase 24 Q9Y6E0 STK24_HUMAN Homo sapiens 3 0.8171
Serine/threonine-protein kinase 24 Q9Y6E0 STK24_HUMAN Homo sapiens 3 0.8171
Norsolorinic acid synthase Q12053 AFLC_ASPPU Aspergillus parasiticus 3 0.7984
Norsolorinic acid synthase Q12053 AFLC_ASPPU Aspergillus parasiticus 3 0.7984
Activin receptor type-1 Q04771 ACVR1_HUMAN Homo sapiens 3 0.7765
Activin receptor type-1 Q04771 ACVR1_HUMAN Homo sapiens 3 0.7765
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7727
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7727
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7615
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7615
Riboflavin synthase P0AFU8 RISA_ECOLI Escherichia coli 4 0.7586
Riboflavin synthase P0AFU8 RISA_ECOLI Escherichia coli 4 0.7586
Ephrin type-B receptor 4 P54760 EPHB4_HUMAN Homo sapiens 3 0.7581
Ephrin type-B receptor 4 P54760 EPHB4_HUMAN Homo sapiens 3 0.7581
Mycocyclosin synthase P9WPP7 CP121_MYCTU Mycobacterium tuberculosis 3 0.7530
Mycocyclosin synthase P9WPP7 CP121_MYCTU Mycobacterium tuberculosis 3 0.7530
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 3 0.7527
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 3 0.7527
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.7508
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.7508
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7364
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7364
Homoserine dehydrogenase P31116 DHOM_YEAST Saccharomyces cerevisiae 3 0.7268
Homoserine dehydrogenase P31116 DHOM_YEAST Saccharomyces cerevisiae 3 0.7268
High affinity 3',5'-cyclic-AMP phosphodiesterase 7A Q13946 PDE7A_HUMAN Homo sapiens 4 0.7256
High affinity 3',5'-cyclic-AMP phosphodiesterase 7A Q13946 PDE7A_HUMAN Homo sapiens 4 0.7256
Polymerase acidic protein C3W5S0 C3W5S0_I09A0 Influenza A virus 2 0.7237
Polymerase acidic protein C3W5S0 C3W5S0_I09A0 Influenza A virus 2 0.7237
NAD(P)H dehydrogenase [quinone] 1 P15559 NQO1_HUMAN Homo sapiens 4 0.7205
NAD(P)H dehydrogenase [quinone] 1 P15559 NQO1_HUMAN Homo sapiens 4 0.7205
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7196
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7196
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7178
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7178
Pancreatic alpha-amylase P04746 AMYP_HUMAN Homo sapiens 2 0.7170
Pancreatic alpha-amylase P04746 AMYP_HUMAN Homo sapiens 2 0.7170
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7170
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7170
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.7167
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.7167
Mitogen-activated protein kinase 14 Q16539 MK14_HUMAN Homo sapiens 3 0.7126
Mitogen-activated protein kinase 14 Q16539 MK14_HUMAN Homo sapiens 3 0.7126
16S rRNA (adenine(1408)-N(1))-methyltransferase A8C927 NPMA_ECOLX Escherichia coli 3 0.7107
16S rRNA (adenine(1408)-N(1))-methyltransferase A8C927 NPMA_ECOLX Escherichia coli 3 0.7107
5'-methylthioadenosine/S-adenosylhomocysteine nucleosidase P0AF12 MTNN_ECOLI Escherichia coli 3 0.7104
5'-methylthioadenosine/S-adenosylhomocysteine nucleosidase P0AF12 MTNN_ECOLI Escherichia coli 3 0.7104
Hypoxanthine-guanine phosphoribosyltransferase P00492 HPRT_HUMAN Homo sapiens 3 0.7096
Hypoxanthine-guanine phosphoribosyltransferase P00492 HPRT_HUMAN Homo sapiens 3 0.7096
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7090
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7090
3'-5' exoribonuclease Rv2179c P9WJ73 EXRBN_MYCTU Mycobacterium tuberculosis 3 0.7072
3'-5' exoribonuclease Rv2179c P9WJ73 EXRBN_MYCTU Mycobacterium tuberculosis 3 0.7072
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7022
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7022
WxcM-like protein Q12KT8 Q12KT8_SHEDO Shewanella denitrificans 3 0.7003
WxcM-like protein Q12KT8 Q12KT8_SHEDO Shewanella denitrificans 3 0.7003

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