Dehydrodiconiferyl alcohol 9,9’-diacetate - Compound Card

Dehydrodiconiferyl alcohol 9,9’-diacetate

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Dehydrodiconiferyl alcohol 9,9’-diacetate

Structure
Zoomed Structure
  • Family: Plantae - Capparaceae
  • Kingdom: Plantae
  • Class: Lignan
    • Subclass: Benzofuran
Canonical Smiles COc1cc(/C=C/COC(=O)C)cc2c1OC([C@@H]2COC(=O)C)c1ccc(c(c1)OC)O
InChI InChI=1S/C24H26O8/c1-14(25)30-9-5-6-16-10-18-19(13-31-15(2)26)23(32-24(18)22(11-16)29-4)17-7-8-20(27)21(12-17)28-3/h5-8,10-12,19,23,27H,9,13H2,1-4H3/b6-5+/t19-,23?/m1/s1
InChIKey TYXVTGSQLKCKCF-TZRGYGLNSA-N
Formula C24H26O8
HBA 8
HBD 1
MW 442.46
Rotatable Bonds 8
TPSA 100.52
LogP 3.77
Number Rings 3
Number Aromatic Rings 2
Heavy Atom Count 32
Formal Charge 0
Fraction CSP3 0.33
Exact Mass 442.16
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Cleome arabica Capparaceae Plantae 511509

Showing of synonyms

  • Ladhari A, Tufano I, et al. (2020). Influence of new effective allelochemicals on the distribution of Cleome arabica L. community in nature. Natural product research, 2020, 34(6), 773-781. [View] [PubMed]

No compound-protein relationship available.

Structure

SMILES: c1cccc(c12)OC(C2)c3ccccc3

Level: 1

Mol. Weight: 442.46 g/mol

Structure

SMILES: C1COc(c12)cccc2

Level: 0

Mol. Weight: 442.46 g/mol

Structure

SMILES: c1ccccc1

Level: 0

Mol. Weight: 442.46 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.39
Human Oral Bioavailability 20%
Non-Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.610
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.25

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
1.130
Plasma Protein Binding
69.36
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
Substrate
CYP 2D6 Inhibitor
Non-Inhibitor
CYP 2D6 Substrate
Non-Substrate
CYP 3A4 Inhibitor
Inhibitor
CYP 3A4 Substrate
Non-Substrate
OATP1B1
Non-Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
10.870
Organic Cation Transporter 2
Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
1.430
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
1.130
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
7.060
Micronucleos
Toxic
NR-AhR
Safe
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
Safe
T. Pyriformis
-72.030
Rat (Acute)
2.250
Rat (Chronic Oral)
2.590
Fathead Minnow
5.390
Respiratory Disease
Safe
Skin Sensitisation
Safe
SR-ARE
Toxic
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Safe

General Properties

Boiling Point
468.940
Hydration Free Energy
-3.040
Log(D) at pH=7.4
3.640
Log(P)
2.89
Log S
-5.75
Log(Vapor Pressure)
-8.44
Melting Point
126.75
pKa Acid
9.57
pKa Basic
2.94
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.9374
Cathepsin S P25774 CATS_HUMAN Homo sapiens 3 0.9359
Serine/threonine-protein kinase 24 Q9Y6E0 STK24_HUMAN Homo sapiens 3 0.9334
Serine/threonine-protein kinase 10 O94804 STK10_HUMAN Homo sapiens 3 0.9150
D-aminoacyl-tRNA deacylase Q8IIS0 DTD_PLAF7 Plasmodium falciparum 3 0.9058
Flavoredoxin Q72HI0 Q72HI0_THET2 Thermus thermophilus 3 0.9027
Thymidylate synthase P00469 TYSY_LACCA Lacticaseibacillus casei 3 0.8914
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 3 0.8797
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.8764
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 3 0.8750
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.8725
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.8718
Thymidine phosphorylase Q7CP66 TYPH_SALTY Salmonella typhimurium 3 0.8706
Stromelysin-1 P08254 MMP3_HUMAN Homo sapiens 3 0.8685
Mycocyclosin synthase P9WPP7 CP121_MYCTU Mycobacterium tuberculosis 4 0.8657
UDP-N-acetylmuramoyl-tripeptide--D-alanyl-D-alanine ligase Q8DNV6 Q8DNV6_STRR6 Streptococcus pneumoniae 3 0.8652
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.8635
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8630
NAD-capped RNA hydrolase NudC P32664 NUDC_ECOLI Escherichia coli 3 0.8624
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 3 0.8602
Mycocyclosin synthase P9WPP7 CP121_MYCTU Mycobacterium tuberculosis 3 0.8483
Streptogramin A acetyltransferase P50870 VATD_ENTFC Enterococcus faecium 3 0.8452
Serine/threonine-protein kinase 24 Q9Y6E0 STK24_HUMAN Homo sapiens 3 0.8385
Pancreatic alpha-amylase P04746 AMYP_HUMAN Homo sapiens 3 0.8379
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.8243
Mycocyclosin synthase P9WPP7 CP121_MYCTU Mycobacterium tuberculosis 3 0.8225
Probable NDP-rhamnosyltransferase Q9ALM8 Q9ALM8_SACSN Saccharopolyspora spinosa 3 0.8219
Proliferating cell nuclear antigen P12004 PCNA_HUMAN Homo sapiens 3 0.8211
ActVA 6 protein Q53908 Q53908_STRCH Streptomyces coelicolor 3 0.8126
N-alpha-acetyltransferase 50 Q9GZZ1 NAA50_HUMAN Homo sapiens 3 0.8090
Purine nucleoside phosphorylase P00491 PNPH_HUMAN Homo sapiens 3 0.8065
Cytochrome P450 1A1 P04798 CP1A1_HUMAN Homo sapiens 3 0.8063
Acetolactate synthase, chloroplastic P17597 ILVB_ARATH Arabidopsis thaliana 3 0.8018
GCN5-related N-acetyltransferase B1YEL6 B1YEL6_EXIS2 Exiguobacterium sibiricum 3 0.7997
GCN5-related N-acetyltransferase B1YEL6 B1YEL6_EXIS2 Exiguobacterium sibiricum 3 0.7987
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7982
Steroid C26-monooxygenase P9WPP1 CP125_MYCTU Mycobacterium tuberculosis 3 0.7981
Aldo-keto reductase family 1 member B1 P15121 ALDR_HUMAN Homo sapiens 3 0.7963
Rhodopsin kinase GRK1 P28327 GRK1_BOVIN Bos taurus 3 0.7861
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7834
Histone deacetylase 8 Q9BY41 HDAC8_HUMAN Homo sapiens 3 0.7833
DNA polymerase III subunit epsilon P03007 DPO3E_ECOLI Escherichia coli 3 0.7821
DNA gyrase subunit A P0AES5 GYRA_SHIFL Shigella flexneri 3 0.7817
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7793
Mitogen-activated protein kinase 1 P28482 MK01_HUMAN Homo sapiens 3 0.7749
NADPH-dependent oxidoreductase 2-alkenal reductase Q39172 AER_ARATH Arabidopsis thaliana 3 0.7736
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.7727
Pantothenate synthetase P9WIL5 PANC_MYCTU Mycobacterium tuberculosis 3 0.7707
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.7699
Histone deacetylase 8 Q9BY41 HDAC8_HUMAN Homo sapiens 3 0.7678
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7673
Gag-Pol polyprotein P03367 POL_HV1BR Human immunodeficiency virus type 1 group M subtype B 3 0.7663
Genome polyprotein P26663 POLG_HCVBK Hepatitis C virus genotype 1b 3 0.7656
4-hydroxyphenylacetate 3-monooxygenase, reductase component Q5SJP7 HPAC_THET8 Thermus thermophilus 3 0.7648
rRNA N-glycosylase D9J2T9 D9J2T9_MOMBA Momordica balsamina 3 0.7648
Nodulin-13 P93330 NOD13_MEDTR Medicago truncatula 3 0.7616
Macrophage metalloelastase P39900 MMP12_HUMAN Homo sapiens 3 0.7610
17beta-hydroxysteroid dehydrogenase O93874 O93874_COCLU Cochliobolus lunatus 3 0.7607
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7584
Transthyretin P02767 TTHY_RAT Rattus norvegicus 3 0.7581
Tyrosine-protein kinase Lck P06239 LCK_HUMAN Homo sapiens 3 0.7571
Thymidylate synthase Q4JQW2 TYSY_VZVO Varicella-zoster virus 3 0.7566
Adenylate cyclase type 5 P30803 ADCY5_CANLF Canis lupus familiaris 3 0.7558
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.7544
Gastrotropin P51161 FABP6_HUMAN Homo sapiens 3 0.7479
MAP kinase-activated protein kinase 2 P49137 MAPK2_HUMAN Homo sapiens 3 0.7479
Deoxynucleoside triphosphate triphosphohydrolase SAMHD1 Q9Y3Z3 SAMH1_HUMAN Homo sapiens 3 0.7461
HTH-type transcriptional regulator TtgR Q9AIU0 TTGR_PSEPT Pseudomonas putida 4 0.7460
Fibroblast growth factor receptor 1 P11362 FGFR1_HUMAN Homo sapiens 3 0.7460
Beta-glucuronidase P05804 BGLR_ECOLI Escherichia coli 3 0.7454
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7441
Albumin P02768 ALBU_HUMAN Homo sapiens 3 0.7437
Oxygenase Q194P4 Q194P4_STRAA Streptomyces argillaceus 3 0.7430
Ephrin type-B receptor 4 P54760 EPHB4_HUMAN Homo sapiens 3 0.7412
Orotidine 5'-phosphate decarboxylase Q5L0U0 PYRF_GEOKA Geobacillus kaustophilus 3 0.7410
Glucan 1,3-beta-glucosidase P29717 EXG1_CANAL Candida albicans 2 0.7406
Glucan 1,3-beta-glucosidase P29717 EXG1_CANAL Candida albicans 2 0.7400
Glutathione S-transferase P P09211 GSTP1_HUMAN Homo sapiens 2 0.7396
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7394
Tyrosine-protein kinase Lck P06239 LCK_HUMAN Homo sapiens 3 0.7372
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7368
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7362
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7353
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7352
Adenylate cyclase type 5 P30803 ADCY5_CANLF Canis lupus familiaris 3 0.7350
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 3 0.7347
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase Q05603 COBT_SALTY Salmonella typhimurium 2 0.7347
[LysW]-aminoadipate kinase O50147 LYSZ_THET2 Thermus thermophilus 3 0.7333
Tau-tubulin kinase 1 Q5TCY1 TTBK1_HUMAN Homo sapiens 3 0.7316
Polymerase acidic protein C3W5S0 C3W5S0_I09A0 Influenza A virus 2 0.7311
ALK tyrosine kinase receptor Q9UM73 ALK_HUMAN Homo sapiens 3 0.7306
Cytochrome P450 130 P9WPN5 CP130_MYCTU Mycobacterium tuberculosis 3 0.7300
CCA-adding enzyme O28126 CCA_ARCFU Archaeoglobus fulgidus 2 0.7299
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7296
Mitogen-activated protein kinase 14 Q16539 MK14_HUMAN Homo sapiens 4 0.7292
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7291
Mitochondrial poly(A) polymerase F1NBW0 F1NBW0_CHICK Gallus gallus 2 0.7284
Phospholipase A2, major isoenzyme P00592 PA21B_PIG Sus scrofa 3 0.7239
Beta-galactoside-specific lectin 4 Q6ITZ3 ML4_VISAL Viscum album 2 0.7230
Alpha-ketoglutarate-dependent dioxygenase FTO Q9C0B1 FTO_HUMAN Homo sapiens 3 0.7223
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7222
Histone deacetylase 4 P56524 HDAC4_HUMAN Homo sapiens 2 0.7222
Lethal factor P15917 LEF_BACAN Bacillus anthracis 3 0.7219
Cytohesin-2 Q99418 CYH2_HUMAN Homo sapiens 3 0.7217
Ephrin type-B receptor 2 P54763 EPHB2_MOUSE Mus musculus 2 0.7217
Protein LlR18A P52778 L18A_LUPLU Lupinus luteus 3 0.7212
3-hydroxyanthranilate 3,4-dioxygenase Q1LCS4 3HAO_CUPMC Cupriavidus metallidurans 2 0.7211
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7204
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 3 0.7202
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7201
Gag-Pol polyprotein P12497 POL_HV1N5 Human immunodeficiency virus type 1 group M subtype B 2 0.7200
Vitamin D-binding protein P02774 VTDB_HUMAN Homo sapiens 2 0.7199
L-methionine gamma-lyase Q84AR1 Q84AR1_CITFR Citrobacter freundii 3 0.7195
WxcM-like protein Q12KT8 Q12KT8_SHEDO Shewanella denitrificans 3 0.7194
UDP-galactopyranose mutase Q48485 GLF1_KLEPN Klebsiella pneumoniae 3 0.7190
Flavin-dependent monooxygenase Q93L51 TETX_BACT4 Bacteroides thetaiotaomicron 2 0.7183
Vascular endothelial growth factor receptor 2 P35968 VGFR2_HUMAN Homo sapiens 3 0.7182
Endothiapepsin P11838 CARP_CRYPA Cryphonectria parasitica 2 0.7181
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7176
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7174
Cytosolic purine 5'-nucleotidase P49902 5NTC_HUMAN Homo sapiens 2 0.7171
Serine/threonine-protein kinase SKY1 Q03656 SKY1_YEAST Saccharomyces cerevisiae 2 0.7167
Riboflavin synthase P0AFU8 RISA_ECOLI Escherichia coli 3 0.7162
Metallo-beta-lactamase type 2 C7C422 BLAN1_KLEPN Klebsiella pneumoniae 2 0.7155
cAMP-dependent protein kinase regulatory subunit P07278 KAPR_YEAST Saccharomyces cerevisiae 3 0.7146
Gag-Pol polyprotein P03367 POL_HV1BR Human immunodeficiency virus type 1 group M subtype B 3 0.7137
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7135
Estrogen receptor P03372 ESR1_HUMAN Homo sapiens 3 0.7133
Nitric oxide synthase oxygenase O34453 NOSO_BACSU Bacillus subtilis 3 0.7132
Succinate dehydrogenase flavoprotein subunit P0AC41 SDHA_ECOLI Escherichia coli 3 0.7131
Peroxisome proliferator-activated receptor gamma P37231 PPARG_HUMAN Homo sapiens 3 0.7125
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 2 0.7122
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7110
Mitogen-activated protein kinase 14 Q16539 MK14_HUMAN Homo sapiens 3 0.7106
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7077
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7075
Carbonic anhydrase 4 P22748 CAH4_HUMAN Homo sapiens 3 0.7072
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7071
FMN-dependent NAD(P)H:quinone oxidoreductase 1 Q9I5F3 AZOR1_PSEAE Pseudomonas aeruginosa 2 0.7059
3-hydroxybenzoate 4-monooxygenase Q6SSJ6 MOBA_COMTE Comamonas testosteroni 2 0.7057
Gag-Pol polyprotein P03367 POL_HV1BR Human immunodeficiency virus type 1 group M subtype B 3 0.7046
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7024
DNA-directed DNA polymerase Q38087 DPOL_BPR69 Escherichia phage RB69 2 0.7021
CCA-adding enzyme O28126 CCA_ARCFU Archaeoglobus fulgidus 2 0.7019
Pheromone-binding protein ASP1 Q9U9J6 Q9U9J6_APIME Apis mellifera 2 0.7015
cGMP-dependent 3',5'-cyclic phosphodiesterase O00408 PDE2A_HUMAN Homo sapiens 3 0.7013
Cyclic dipeptide N-prenyltransferase D1D8L6 D1D8L6_ASPFM Neosartorya fumigata 2 0.7005
Non-receptor tyrosine-protein kinase TYK2 P29597 TYK2_HUMAN Homo sapiens 3 0.7004
2-phospho-L-lactate transferase Q8PVT6 COFD_METMA Methanosarcina mazei 3 0.7003

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