4,5-dimethoxy-3',4'-methylenedioxy-2,7'-cycloligna-7,7'-diene - Compound Card

4,5-dimethoxy-3',4'-methylenedioxy-2,7'-cycloligna-7,7'-diene

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4,5-dimethoxy-3',4'-methylenedioxy-2,7'-cycloligna-7,7'-diene

Structure
Zoomed Structure
  • Family: Plantae - Myristicaceae
  • Kingdom: Plantae
  • Class: Lignan
Canonical Smiles COc1cc2cc(C)c(c(c2cc1OC)c1ccc2c(c1)OCO2)C
InChI InChI=1S/C21H20O4/c1-12-7-15-9-18(22-3)19(23-4)10-16(15)21(13(12)2)14-5-6-17-20(8-14)25-11-24-17/h5-10H,11H2,1-4H3
InChIKey PZXYEQWDASHMDR-UHFFFAOYSA-N
Formula C21H20O4
HBA 4
HBD 0
MW 336.39
Rotatable Bonds 3
TPSA 36.92
LogP 4.87
Number Rings 4
Number Aromatic Rings 3
Heavy Atom Count 25
Formal Charge 0
Fraction CSP3 0.24
Exact Mass 336.14
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Pycnanthus angolensis Myristicaceae Plantae 224864

Showing of synonyms

  • Kuete V, Nono EC, et al. (2011). Antimicrobial activities of the CH2Cl2-CH3OH (1:1) extracts and compounds from the roots and fruits of Pycnanthus angolensis (Myristicaceae).. Natural product research,2011, 25(4), 432-443. [View] [PubMed]
Pubchem: 71340713
Nmrshiftdb2: 60075721

No compound-protein relationship available.

Structure

SMILES: O1COc(c12)ccc(c2)-c3cccc(c34)cccc4

Level: 1

Mol. Weight: 336.39 g/mol

Structure

SMILES: c1cccc(c12)cccc2

Level: 0

Mol. Weight: 336.39 g/mol

Structure

SMILES: O1COc(c12)cccc2

Level: 0

Mol. Weight: 336.39 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-5.13
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.660
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.21

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
1.700
Plasma Protein Binding
81.79
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
Substrate
OATP1B1
Non-Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
11.240
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
2.360
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Toxic
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
1.410
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
7.000
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
Toxic
T. Pyriformis
0.840
Rat (Acute)
2.290
Rat (Chronic Oral)
1.710
Fathead Minnow
5.480
Respiratory Disease
Safe
Skin Sensitisation
Toxic
SR-ARE
Toxic
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Safe

General Properties

Boiling Point
453.190
Hydration Free Energy
-6.350
Log(D) at pH=7.4
3.830
Log(P)
5.26
Log S
-5.78
Log(Vapor Pressure)
-7.11
Melting Point
121.3
pKa Acid
10.68
pKa Basic
1.52
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.9311
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.9157
Bromodomain-containing protein 2 P25440 BRD2_HUMAN Homo sapiens 3 0.9138
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.9026
HTH-type transcriptional regulator QacR P0A0N4 QACR_STAAU Staphylococcus aureus 3 0.9018
E3 ubiquitin-protein ligase Mdm2 Q00987 MDM2_HUMAN Homo sapiens 3 0.8807
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.8771
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform O02697 PK3CG_PIG Sus scrofa 3 0.8712
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.8662
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.8610
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 3 0.8598
Gag-Pol polyprotein P12497 POL_HV1N5 Human immunodeficiency virus type 1 group M subtype B 3 0.8538
Bromodomain adjacent to zinc finger domain protein 2B Q9UIF8 BAZ2B_HUMAN Homo sapiens 3 0.8526
Methionine aminopeptidase 2 P9WK19 MAP12_MYCTU Mycobacterium tuberculosis 3 0.8488
Bromodomain testis-specific protein Q58F21 BRDT_HUMAN Homo sapiens 3 0.8483
Gag-Pol polyprotein P03366 POL_HV1B1 Human immunodeficiency virus type 1 group M subtype B 3 0.8472
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8449
Flavin reductase (NADPH) P30043 BLVRB_HUMAN Homo sapiens 3 0.8399
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.8379
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.8270
Cathepsin S P25774 CATS_HUMAN Homo sapiens 3 0.8224
Methionine aminopeptidase P0AE18 MAP1_ECOLI Escherichia coli 3 0.8221
Methionine aminopeptidase P0AE18 MAP1_ECOLI Escherichia coli 3 0.8218
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.8123
Glutamate receptor 2 P19491 GRIA2_RAT Rattus norvegicus 3 0.8087
Aldo-keto reductase family 1 member B1 P15121 ALDR_HUMAN Homo sapiens 3 0.8024
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7993
Bromodomain-containing protein 2 P25440 BRD2_HUMAN Homo sapiens 3 0.7920
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.7910
Gag-Pol polyprotein P04585 POL_HV1H2 Human immunodeficiency virus type 1 group M subtype B 3 0.7891
Glucose-1-phosphate thymidylyltransferase Q9HU22 Q9HU22_PSEAE Pseudomonas aeruginosa 3 0.7842
Catechol O-methyltransferase P22734 COMT_RAT Rattus norvegicus 3 0.7840
Alpha-ketoglutarate-dependent dioxygenase FTO Q9C0B1 FTO_HUMAN Homo sapiens 3 0.7816
Albumin P02769 ALBU_BOVIN Bos taurus 3 0.7805
Estrogen receptor P03372 ESR1_HUMAN Homo sapiens 3 0.7784
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.7716
Gag-Pol polyprotein P03366 POL_HV1B1 Human immunodeficiency virus type 1 group M subtype B 3 0.7712
Glycylpeptide N-tetradecanoyltransferase A5K1A2 A5K1A2_PLAVS Plasmodium vivax 4 0.7702
Gag-Pol polyprotein P12497 POL_HV1N5 Human immunodeficiency virus type 1 group M subtype B 4 0.7698
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.7659
Activin receptor type-1 Q04771 ACVR1_HUMAN Homo sapiens 3 0.7655
Riboflavin synthase P0AFU8 RISA_ECOLI Escherichia coli 3 0.7634
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7626
E3 ubiquitin-protein ligase Mdm2 Q00987 MDM2_HUMAN Homo sapiens 3 0.7619
Progesterone receptor P06401 PRGR_HUMAN Homo sapiens 3 0.7580
Aminoglycoside 3'-phosphotransferase AphA1-IAB B0VD92 B0VD92_ACIBY Acinetobacter baumannii 3 0.7568
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7545
Mycocyclosin synthase P9WPP7 CP121_MYCTU Mycobacterium tuberculosis 3 0.7536
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.7514
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7497
Tyrosine-protein kinase Lck P06239 LCK_HUMAN Homo sapiens 3 0.7489
Casein kinase I isoform gamma-3 Q9Y6M4 KC1G3_HUMAN Homo sapiens 3 0.7487
Progesterone receptor P06401 PRGR_HUMAN Homo sapiens 3 0.7473
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform P48736 PK3CG_HUMAN Homo sapiens 3 0.7446
Sterol 14alpha-demethylase P9WPP9 CP51_MYCTU Mycobacterium tuberculosis 3 0.7431
Serine/threonine-protein kinase 24 Q9Y6E0 STK24_HUMAN Homo sapiens 3 0.7406
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7390
Mycocyclosin synthase P9WPP7 CP121_MYCTU Mycobacterium tuberculosis 3 0.7389
Mycocyclosin synthase P9WPP7 CP121_MYCTU Mycobacterium tuberculosis 3 0.7384
Mitogen-activated protein kinase 10 P53779 MK10_HUMAN Homo sapiens 3 0.7384
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.7346
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7325
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7308
Aldo-keto reductase family 1 member C3 P42330 AK1C3_HUMAN Homo sapiens 4 0.7307
Gag-Pol polyprotein P12497 POL_HV1N5 Human immunodeficiency virus type 1 group M subtype B 3 0.7297
Catechol O-methyltransferase P22734 COMT_RAT Rattus norvegicus 3 0.7282
Glucose-1-phosphate thymidylyltransferase Q9HU22 Q9HU22_PSEAE Pseudomonas aeruginosa 3 0.7278
Methionine aminopeptidase P0AE18 MAP1_ECOLI Escherichia coli 3 0.7241
Gag-Pol polyprotein P04585 POL_HV1H2 Human immunodeficiency virus type 1 group M subtype B 3 0.7238
Neuropilin-1 O14786 NRP1_HUMAN Homo sapiens 3 0.7237
Acetylcholinesterase P21836 ACES_MOUSE Mus musculus 2 0.7218
Aldo-keto reductase family 1 member B10 O60218 AK1BA_HUMAN Homo sapiens 4 0.7211
Casein kinase II subunit alpha P28523 CSK2A_MAIZE Zea mays 3 0.7202
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7198
Gag-Pol polyprotein P12497 POL_HV1N5 Human immunodeficiency virus type 1 group M subtype B 4 0.7194
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7182
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 4 0.7170
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.7137
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 3 0.7128
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 4 0.7107
Serine/threonine-protein kinase pim-1 P11309 PIM1_HUMAN Homo sapiens 3 0.7106
Aldo-keto reductase family 1 member B1 P80276 ALDR_PIG Sus scrofa 3 0.7104
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7091
Pancreatic alpha-amylase P04746 AMYP_HUMAN Homo sapiens 2 0.7091
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7090
Albumin P02768 ALBU_HUMAN Homo sapiens 3 0.7087
Polymerase acidic protein C3W5S0 C3W5S0_I09A0 Influenza A virus 2 0.7071
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7070
Casein kinase II subunit alpha' P19784 CSK22_HUMAN Homo sapiens 3 0.7066
Aldo-keto reductase family 1 member B1 P15121 ALDR_HUMAN Homo sapiens 2 0.7056
Beta-galactoside-specific lectin 4 Q6ITZ3 ML4_VISAL Viscum album 2 0.7055
Orotidine 5'-phosphate decarboxylase O26232 PYRF_METTH Methanothermobacter thermautotrophicus 3 0.7047
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.7046
Thymidylate synthase P0A886 TYSY_ECO57 Escherichia coli O157:H7 2 0.7035
Casein kinase II subunit alpha P28523 CSK2A_MAIZE Zea mays 3 0.7028
Serine/threonine-protein kinase PLK2 Q9NYY3 PLK2_HUMAN Homo sapiens 3 0.7025
Nuclear receptor subfamily 4immunitygroup A member 1 P22736 NR4A1_HUMAN Homo sapiens 2 0.7025
Fibroblast growth factor receptor 1 P11362 FGFR1_HUMAN Homo sapiens 2 0.7014
Gag-Pol polyprotein P12497 POL_HV1N5 Human immunodeficiency virus type 1 group M subtype B 4 0.7008

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