Dehydrodiconiferyl alcohol - Compound Card

Dehydrodiconiferyl alcohol

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Dehydrodiconiferyl alcohol

Structure
Zoomed Structure
  • Family: Plantae - Urticaceae
  • Kingdom: Plantae
  • Class: Lignan
Canonical Smiles OC/C=C/c1cc2c(c(c1)OC)OC(C2CO)c1ccc(c(c1)OC)O
InChI InChI=1S/C20H22O6/c1-24-17-10-13(5-6-16(17)23)19-15(11-22)14-8-12(4-3-7-21)9-18(25-2)20(14)26-19/h3-6,8-10,15,19,21-23H,7,11H2,1-2H3/b4-3+
InChIKey KUSXBOZNRPQEON-ONEGZZNKSA-N
Formula C20H22O6
HBA 6
HBD 3
MW 358.39
Rotatable Bonds 6
TPSA 88.38
LogP 2.62
Number Rings 3
Number Aromatic Rings 2
Heavy Atom Count 26
Formal Charge 0
Fraction CSP3 0.3
Exact Mass 358.14
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Urtica dioica Urticaceae Plantae 3501

Showing of synonyms

  • Schöttner M, Reiner J, et al. (1997). Lignans from the roots of Urtica dioica and their metabolites bind to human sex hormone binding globulin (SHBG). Planta Medica,1997,63(6),529-532. [View] [PubMed]
Pubchem: 5372367
Chebi: 91184
Nmrshiftdb2: 60022659
Metabolights: MTBLC91184
CPRiL: 75080
Structure

SMILES: c1cccc(c12)OC(C2)c3ccccc3

Level: 1

Mol. Weight: 358.39 g/mol

Structure

SMILES: C1COc(c12)cccc2

Level: 0

Mol. Weight: 358.39 g/mol

Structure

SMILES: c1ccccc1

Level: 0

Mol. Weight: 358.39 g/mol

Vasorelaxant

Absorption

Caco-2 (logPapp)
-4.5
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.79
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.39

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
1.15
Plasma Protein Binding
42.42
Steady State Volume of Distribution
-

Metabolism

Breast Cancer Resistance Protein
Non-Inhibitor
CYP 1A2 Inhibitor
Non-Inhibitor
CYP 1A2 Substrate
Substrate
CYP 2C19 Inhibitor
Non-Inhibitor
CYP 2C19 Substrate
Non-Substrate
CYP 2C9 Inhibitor
Non-Inhibitor
CYP 2C9 Substrate
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
9.41
Organic Cation Transporter 2
Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
1.6
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.82
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
5.18
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
-2.18
Rat (Acute)
2.03
Rat (Chronic Oral)
2.93
Fathead Minnow
4.87
Respiratory Disease
Toxic
Skin Sensitisation
Safe
SR-ARE
Toxic
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Safe

General Properties

Boiling Point
439.92
Hydration Free Energy
-7.99
Log(D) at pH=7.4
2.37
Log(P)
1.28
Log S
-4.13
Log(Vapor Pressure)
-7.72
Melting Point
147.25
pKa Acid
8.54
pKa Basic
1.68
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
D-aminoacyl-tRNA deacylase Q8IIS0 DTD_PLAF7 Plasmodium falciparum 3 0.9153
D-aminoacyl-tRNA deacylase Q8IIS0 DTD_PLAF7 Plasmodium falciparum 3 0.9153
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 3 0.8765
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 3 0.8765
Thymidine phosphorylase Q7CP66 TYPH_SALTY Salmonella typhimurium 3 0.8760
Thymidine phosphorylase Q7CP66 TYPH_SALTY Salmonella typhimurium 3 0.8760
Mycocyclosin synthase P9WPP7 CP121_MYCTU Mycobacterium tuberculosis 4 0.8691
Mycocyclosin synthase P9WPP7 CP121_MYCTU Mycobacterium tuberculosis 4 0.8691
Stromelysin-1 P08254 MMP3_HUMAN Homo sapiens 3 0.8638
Stromelysin-1 P08254 MMP3_HUMAN Homo sapiens 3 0.8638
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 3 0.8584
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 3 0.8584
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 3 0.8535
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 3 0.8535
Flavoredoxin Q72HI0 Q72HI0_THET2 Thermus thermophilus 3 0.8461
Flavoredoxin Q72HI0 Q72HI0_THET2 Thermus thermophilus 3 0.8461
Xylose isomerase P24300 XYLA_STRRU Streptomyces rubiginosus 3 0.8442
Xylose isomerase P24300 XYLA_STRRU Streptomyces rubiginosus 3 0.8442
Mycocyclosin synthase P9WPP7 CP121_MYCTU Mycobacterium tuberculosis 3 0.8441
Mycocyclosin synthase P9WPP7 CP121_MYCTU Mycobacterium tuberculosis 3 0.8441
Protein ppBat Q8A8A4 Q8A8A4_BACTN Bacteroides thetaiotaomicron VPI-5482 3 0.8250
Protein ppBat Q8A8A4 Q8A8A4_BACTN Bacteroides thetaiotaomicron VPI-5482 3 0.8250
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8241
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8241
rRNA N-glycosylase D9J2T9 D9J2T9_MOMBA Momordica balsamina 3 0.8199
rRNA N-glycosylase D9J2T9 D9J2T9_MOMBA Momordica balsamina 3 0.8199
Purine nucleoside phosphorylase P00491 PNPH_HUMAN Homo sapiens 3 0.8178
Purine nucleoside phosphorylase P00491 PNPH_HUMAN Homo sapiens 3 0.8178
Hypoxanthine phosphoribosyltransferase Q4DRC4 Q4DRC4_TRYCC Trypanosoma cruzi 3 0.8028
Hypoxanthine phosphoribosyltransferase Q4DRC4 Q4DRC4_TRYCC Trypanosoma cruzi 3 0.8028
Pantothenate synthetase P9WIL5 PANC_MYCTU Mycobacterium tuberculosis 3 0.8023
Pantothenate synthetase P9WIL5 PANC_MYCTU Mycobacterium tuberculosis 3 0.8023
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 3 0.7994
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 3 0.7994
Serine/threonine-protein kinase 24 Q9Y6E0 STK24_HUMAN Homo sapiens 3 0.7965
Serine/threonine-protein kinase 24 Q9Y6E0 STK24_HUMAN Homo sapiens 3 0.7965
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7939
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7939
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.7924
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.7924
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7906
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7906
Mitogen-activated protein kinase 1 P28482 MK01_HUMAN Homo sapiens 3 0.7904
Mitogen-activated protein kinase 1 P28482 MK01_HUMAN Homo sapiens 3 0.7904
Histone deacetylase 8 Q9BY41 HDAC8_HUMAN Homo sapiens 3 0.7730
Histone deacetylase 8 Q9BY41 HDAC8_HUMAN Homo sapiens 3 0.7730
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.7709
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.7709
Cathepsin S P25774 CATS_HUMAN Homo sapiens 3 0.7701
Cathepsin S P25774 CATS_HUMAN Homo sapiens 3 0.7701
Streptavidin P22629 SAV_STRAV Streptomyces avidinii 3 0.7670
Streptavidin P22629 SAV_STRAV Streptomyces avidinii 3 0.7670
GCN5-related N-acetyltransferase B1YEL6 B1YEL6_EXIS2 Exiguobacterium sibiricum 3 0.7649
GCN5-related N-acetyltransferase B1YEL6 B1YEL6_EXIS2 Exiguobacterium sibiricum 3 0.7649
GCN5-related N-acetyltransferase B1YEL6 B1YEL6_EXIS2 Exiguobacterium sibiricum 3 0.7618
GCN5-related N-acetyltransferase B1YEL6 B1YEL6_EXIS2 Exiguobacterium sibiricum 3 0.7618
Proliferating cell nuclear antigen P12004 PCNA_HUMAN Homo sapiens 3 0.7613
Proliferating cell nuclear antigen P12004 PCNA_HUMAN Homo sapiens 3 0.7613
Histone deacetylase 8 Q9BY41 HDAC8_HUMAN Homo sapiens 3 0.7572
Histone deacetylase 8 Q9BY41 HDAC8_HUMAN Homo sapiens 3 0.7572
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.7562
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.7562
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.7560
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.7560
Dual specificity mitogen-activated protein kinase kinase 1 Q02750 MP2K1_HUMAN Homo sapiens 3 0.7552
Dual specificity mitogen-activated protein kinase kinase 1 Q02750 MP2K1_HUMAN Homo sapiens 3 0.7552
cGMP-dependent 3',5'-cyclic phosphodiesterase O00408 PDE2A_HUMAN Homo sapiens 3 0.7536
cGMP-dependent 3',5'-cyclic phosphodiesterase O00408 PDE2A_HUMAN Homo sapiens 3 0.7536
Gag-Pol polyprotein P03367 POL_HV1BR Human immunodeficiency virus type 1 group M subtype B 3 0.7525
Gag-Pol polyprotein P03367 POL_HV1BR Human immunodeficiency virus type 1 group M subtype B 3 0.7525
Mitogen-activated protein kinase 14 Q16539 MK14_HUMAN Homo sapiens 3 0.7436
Mitogen-activated protein kinase 14 Q16539 MK14_HUMAN Homo sapiens 3 0.7436
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 3 0.7427
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 3 0.7427
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7424
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7424
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7375
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7375
Mycocyclosin synthase P9WPP7 CP121_MYCTU Mycobacterium tuberculosis 3 0.7322
Mycocyclosin synthase P9WPP7 CP121_MYCTU Mycobacterium tuberculosis 3 0.7322
Bromodomain-containing protein 2 P25440 BRD2_HUMAN Homo sapiens 3 0.7318
Bromodomain-containing protein 2 P25440 BRD2_HUMAN Homo sapiens 3 0.7318
Lethal factor P15917 LEF_BACAN Bacillus anthracis 3 0.7294
Lethal factor P15917 LEF_BACAN Bacillus anthracis 3 0.7294
Polymerase acidic protein C3W5S0 C3W5S0_I09A0 Influenza A virus 2 0.7279
Polymerase acidic protein C3W5S0 C3W5S0_I09A0 Influenza A virus 2 0.7279
Catechol O-methyltransferase P22734 COMT_RAT Rattus norvegicus 3 0.7273
Catechol O-methyltransferase P22734 COMT_RAT Rattus norvegicus 3 0.7273
Methylmalonyl-CoA decarboxylase P52045 SCPB_ECOLI Escherichia coli 3 0.7259
Methylmalonyl-CoA decarboxylase P52045 SCPB_ECOLI Escherichia coli 3 0.7259
Non-receptor tyrosine-protein kinase TYK2 P29597 TYK2_HUMAN Homo sapiens 3 0.7250
Non-receptor tyrosine-protein kinase TYK2 P29597 TYK2_HUMAN Homo sapiens 3 0.7250
Abscisic acid receptor PYL2 O80992 PYL2_ARATH Arabidopsis thaliana 3 0.7236
Abscisic acid receptor PYL2 O80992 PYL2_ARATH Arabidopsis thaliana 3 0.7236
Beta-galactoside-specific lectin 4 Q6ITZ3 ML4_VISAL Viscum album 2 0.7224
Beta-galactoside-specific lectin 4 Q6ITZ3 ML4_VISAL Viscum album 2 0.7224
WxcM-like protein Q12KT8 Q12KT8_SHEDO Shewanella denitrificans 3 0.7220
WxcM-like protein Q12KT8 Q12KT8_SHEDO Shewanella denitrificans 3 0.7220
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7192
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7192
Serine/threonine-protein kinase SKY1 Q03656 SKY1_YEAST Saccharomyces cerevisiae 2 0.7163
Serine/threonine-protein kinase SKY1 Q03656 SKY1_YEAST Saccharomyces cerevisiae 2 0.7163
Dual specificity mitogen-activated protein kinase kinase 1 Q02750 MP2K1_HUMAN Homo sapiens 3 0.7157
Dual specificity mitogen-activated protein kinase kinase 1 Q02750 MP2K1_HUMAN Homo sapiens 3 0.7157
Cytidine and deoxycytidylate deaminase zinc-binding region Q82Y41 Q82Y41_NITEU Nitrosomonas europaea 2 0.7154
Cytidine and deoxycytidylate deaminase zinc-binding region Q82Y41 Q82Y41_NITEU Nitrosomonas europaea 2 0.7154
Peroxisome proliferator-activated receptor gamma P37231 PPARG_HUMAN Homo sapiens 3 0.7143
Peroxisome proliferator-activated receptor gamma P37231 PPARG_HUMAN Homo sapiens 3 0.7143
Phosphatidylinositol 5-phosphate 4-kinase type-2 beta P78356 PI42B_HUMAN Homo sapiens 3 0.7120
Phosphatidylinositol 5-phosphate 4-kinase type-2 beta P78356 PI42B_HUMAN Homo sapiens 3 0.7120
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7112
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7112
dTDP-4-dehydrorhamnose 3,5-epimerase A0A6L7H6N0 A0A1S0QLH9_BACAN Bacillus anthracis 3 0.7101
dTDP-4-dehydrorhamnose 3,5-epimerase A0A6L7H6N0 A0A1S0QLH9_BACAN Bacillus anthracis 3 0.7101
Histone-lysine N-methyltransferase EHMT1 Q9H9B1 EHMT1_HUMAN Homo sapiens 3 0.7100
Histone-lysine N-methyltransferase EHMT1 Q9H9B1 EHMT1_HUMAN Homo sapiens 3 0.7100
Nitric oxide synthase oxygenase O34453 NOSO_BACSU Bacillus subtilis 3 0.7099
Nitric oxide synthase oxygenase O34453 NOSO_BACSU Bacillus subtilis 3 0.7099
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7082
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7082
Chalcone--flavanone isomerase 1 P28012 CFI1_MEDSA Medicago sativa 3 0.7079
Chalcone--flavanone isomerase 1 P28012 CFI1_MEDSA Medicago sativa 3 0.7079
Steroid C26-monooxygenase P9WPP1 CP125_MYCTU Mycobacterium tuberculosis 3 0.7066
Steroid C26-monooxygenase P9WPP1 CP125_MYCTU Mycobacterium tuberculosis 3 0.7066
Threonine--tRNA ligase P0A8M3 SYT_ECOLI Escherichia coli 3 0.7063
Threonine--tRNA ligase P0A8M3 SYT_ECOLI Escherichia coli 3 0.7063
S-adenosylmethionine decarboxylase proenzyme P17707 DCAM_HUMAN Homo sapiens 3 0.7062
S-adenosylmethionine decarboxylase proenzyme P17707 DCAM_HUMAN Homo sapiens 3 0.7062
Catechol O-methyltransferase P22734 COMT_RAT Rattus norvegicus 3 0.7055
Catechol O-methyltransferase P22734 COMT_RAT Rattus norvegicus 3 0.7055
Ethylene receptor 1 P49333 ETR1_ARATH Arabidopsis thaliana 3 0.7053
Ethylene receptor 1 P49333 ETR1_ARATH Arabidopsis thaliana 3 0.7053
Angiotensin-converting enzyme 2 Q9BYF1 ACE2_HUMAN Homo sapiens 2 0.7052
Angiotensin-converting enzyme 2 Q9BYF1 ACE2_HUMAN Homo sapiens 2 0.7052
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.7048
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.7048
Ephrin type-B receptor 2 P54763 EPHB2_MOUSE Mus musculus 2 0.7044
Ephrin type-B receptor 2 P54763 EPHB2_MOUSE Mus musculus 2 0.7044
Non-receptor tyrosine-protein kinase TYK2 P29597 TYK2_HUMAN Homo sapiens 3 0.7043
Non-receptor tyrosine-protein kinase TYK2 P29597 TYK2_HUMAN Homo sapiens 3 0.7043
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7031
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7031
Tyrosine-protein kinase JAK3 P52333 JAK3_HUMAN Homo sapiens 4 0.7020
Tyrosine-protein kinase JAK3 P52333 JAK3_HUMAN Homo sapiens 4 0.7020
Hypoxanthine-guanine phosphoribosyltransferase P00492 HPRT_HUMAN Homo sapiens 3 0.7018
Hypoxanthine-guanine phosphoribosyltransferase P00492 HPRT_HUMAN Homo sapiens 3 0.7018
Histone-lysine N-methyltransferase, H3 lysine-9 specific SUVH4 Q8GZB6 SUVH4_ARATH Arabidopsis thaliana 3 0.7016
Histone-lysine N-methyltransferase, H3 lysine-9 specific SUVH4 Q8GZB6 SUVH4_ARATH Arabidopsis thaliana 3 0.7016
Rhodopsin kinase GRK1 P28327 GRK1_BOVIN Bos taurus 3 0.7015
Rhodopsin kinase GRK1 P28327 GRK1_BOVIN Bos taurus 3 0.7015
Homoserine dehydrogenase P31116 DHOM_YEAST Saccharomyces cerevisiae 3 0.7015
Homoserine dehydrogenase P31116 DHOM_YEAST Saccharomyces cerevisiae 3 0.7015
Soluble cytochrome b562 P0ABE7 C562_ECOLX Escherichia coli 3 0.7008
Soluble cytochrome b562 P0ABE7 C562_ECOLX Escherichia coli 3 0.7008
Cytosolic purine 5'-nucleotidase P49902 5NTC_HUMAN Homo sapiens 2 0.7001
Cytosolic purine 5'-nucleotidase P49902 5NTC_HUMAN Homo sapiens 2 0.7001

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