Dihydrodehydrodiconiferyl alcohol - Compound Card

Dihydrodehydrodiconiferyl alcohol

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Dihydrodehydrodiconiferyl alcohol

Structure
Zoomed Structure
  • Family: Plantae - Celastraceae
  • Kingdom: Plantae
  • Class: Lignan
Canonical Smiles OCCCc1cc2c(c(c1)OC)OC(C2CO)c1ccc(c(c1)OC)O
InChI InChI=1S/C20H24O6/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/h5-6,8-10,15,19,21-23H,3-4,7,11H2,1-2H3
InChIKey SBLZVJIHPWRSQQ-UHFFFAOYSA-N
Formula C20H24O6
HBA 6
HBD 3
MW 360.41
Rotatable Bonds 7
TPSA 88.38
LogP 2.54
Number Rings 3
Number Aromatic Rings 2
Heavy Atom Count 26
Formal Charge 0
Fraction CSP3 0.4
Exact Mass 360.16
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Maytenus senegalensis Celastraceae Plantae 256095

Showing of synonyms

  • Okoye FB, Agbo MO, et al. (2014). New neolignan glycoside and an unusual benzoyl malic acid derivative from Maytenus senegalensis leaves. Natural Product Research,2014,29,109-115. [View]
Pubchem: 4365980
Nmrshiftdb2: 60024747
CPRiL: 103574
Structure

SMILES: c1cccc(c12)OC(C2)c3ccccc3

Level: 1

Mol. Weight: 360.41 g/mol

Structure

SMILES: C1COc(c12)cccc2

Level: 0

Mol. Weight: 360.41 g/mol

Structure

SMILES: c1ccccc1

Level: 0

Mol. Weight: 360.41 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.58
Human Oral Bioavailability 20%
Non-Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.83
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.73

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
1.19
Plasma Protein Binding
40.2
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
9.93
Organic Cation Transporter 2
Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
1.41
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.69
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
4.97
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
-1.54
Rat (Acute)
1.99
Rat (Chronic Oral)
2.77
Fathead Minnow
4.48
Respiratory Disease
Toxic
Skin Sensitisation
Safe
SR-ARE
Safe
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Safe

General Properties

Boiling Point
433.54
Hydration Free Energy
-8.06
Log(D) at pH=7.4
2.38
Log(P)
1.24
Log S
-3.74
Log(Vapor Pressure)
-7.87
Melting Point
119.18
pKa Acid
8.89
pKa Basic
2.64
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.9587
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 3 0.9442
Mycocyclosin synthase P9WPP7 CP121_MYCTU Mycobacterium tuberculosis 3 0.9305
Mycocyclosin synthase P9WPP7 CP121_MYCTU Mycobacterium tuberculosis 4 0.9167
D-aminoacyl-tRNA deacylase Q8IIS0 DTD_PLAF7 Plasmodium falciparum 3 0.9142
Thymidine phosphorylase Q7CP66 TYPH_SALTY Salmonella typhimurium 3 0.8820
Flavoredoxin Q72HI0 Q72HI0_THET2 Thermus thermophilus 3 0.8819
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 3 0.8800
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.8647
Cathepsin S P25774 CATS_HUMAN Homo sapiens 3 0.8592
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 3 0.8582
Steroid C26-monooxygenase P9WPP1 CP125_MYCTU Mycobacterium tuberculosis 3 0.8547
Xylose isomerase P24300 XYLA_STRRU Streptomyces rubiginosus 3 0.8531
cAMP-dependent protein kinase type II-beta regulatory subunit P12369 KAP3_RAT Rattus norvegicus 3 0.8514
Tannase B3Y018 B3Y018_LACPN Lactiplantibacillus plantarum 4 0.8434
Thymidylate synthase P0A886 TYSY_ECO57 Escherichia coli O157:H7 3 0.8433
Peroxisome proliferator-activated receptor gamma P37231 PPARG_HUMAN Homo sapiens 3 0.8306
Pantothenate synthetase P9WIL5 PANC_MYCTU Mycobacterium tuberculosis 3 0.8295
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.8268
Nuclear receptor subfamily 4immunitygroup A member 1 P22736 NR4A1_HUMAN Homo sapiens 3 0.8253
Stromelysin-1 P08254 MMP3_HUMAN Homo sapiens 3 0.8246
rRNA N-glycosylase D9J2T9 D9J2T9_MOMBA Momordica balsamina 3 0.8242
Protein ppBat Q8A8A4 Q8A8A4_BACTN Bacteroides thetaiotaomicron VPI-5482 3 0.8237
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.8231
Purine nucleoside phosphorylase P00491 PNPH_HUMAN Homo sapiens 3 0.8218
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.8206
Mycocyclosin synthase P9WPP7 CP121_MYCTU Mycobacterium tuberculosis 3 0.8192
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.8190
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.8158
Abscisic acid receptor PYR1 O49686 PYR1_ARATH Arabidopsis thaliana 3 0.8151
Hypoxanthine phosphoribosyltransferase Q4DRC4 Q4DRC4_TRYCC Trypanosoma cruzi 3 0.8088
Serine/threonine-protein kinase 24 Q9Y6E0 STK24_HUMAN Homo sapiens 3 0.8085
Streptogramin A acetyltransferase P50870 VATD_ENTFC Enterococcus faecium 3 0.8078
Focal adhesion kinase 1 Q05397 FAK1_HUMAN Homo sapiens 4 0.8068
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 3 0.8054
Endoplasmin P14625 ENPL_HUMAN Homo sapiens 4 0.7997
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 3 0.7987
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7968
GCN5-related N-acetyltransferase B1YEL6 B1YEL6_EXIS2 Exiguobacterium sibiricum 3 0.7943
Dual specificity mitogen-activated protein kinase kinase 1 Q02750 MP2K1_HUMAN Homo sapiens 3 0.7924
GCN5-related N-acetyltransferase B1YEL6 B1YEL6_EXIS2 Exiguobacterium sibiricum 3 0.7900
Mitogen-activated protein kinase 1 P28482 MK01_HUMAN Homo sapiens 3 0.7877
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7769
Proliferating cell nuclear antigen P12004 PCNA_HUMAN Homo sapiens 3 0.7747
Gag-Pol polyprotein P03367 POL_HV1BR Human immunodeficiency virus type 1 group M subtype B 3 0.7745
Potassium/sodium hyperpolarization-activated cyclic nucleotide-gated channel 4 Q9Y3Q4 HCN4_HUMAN Homo sapiens 4 0.7728
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform P48736 PK3CG_HUMAN Homo sapiens 3 0.7725
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.7721
GTP 3',8-cyclase P69848 MOAA_STAA8 Staphylococcus aureus 3 0.7709
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7705
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 3 0.7703
Dual specificity mitogen-activated protein kinase kinase 1 Q02750 MP2K1_HUMAN Homo sapiens 3 0.7672
S-adenosylmethionine decarboxylase proenzyme P17707 DCAM_HUMAN Homo sapiens 3 0.7665
Non-receptor tyrosine-protein kinase TYK2 P29597 TYK2_HUMAN Homo sapiens 3 0.7647
Pheromone-binding protein ASP1 Q9U9J6 Q9U9J6_APIME Apis mellifera 3 0.7565
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7561
cGMP-dependent 3',5'-cyclic phosphodiesterase O00408 PDE2A_HUMAN Homo sapiens 3 0.7530
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.7524
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7513
HTH-type transcriptional regulator TtgR Q9AIU0 TTGR_PSEPT Pseudomonas putida 4 0.7501
Non-receptor tyrosine-protein kinase TYK2 P29597 TYK2_HUMAN Homo sapiens 4 0.7495
Kinesin-like protein KIF11 P52732 KIF11_HUMAN Homo sapiens 3 0.7491
Streptavidin P22629 SAV_STRAV Streptomyces avidinii 3 0.7483
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 2 0.7476
cGMP-dependent protein kinase 1 P00516 KGP1_BOVIN Bos taurus 3 0.7475
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7471
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7468
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7436
Kinesin-like protein KIF11 P52732 KIF11_HUMAN Homo sapiens 3 0.7426
Cytochrome P450 1A1 P04798 CP1A1_HUMAN Homo sapiens 3 0.7425
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7421
DNA ligase P43813 DNLJ_HAEIN Haemophilus influenzae 3 0.7410
Mitogen-activated protein kinase 14 Q16539 MK14_HUMAN Homo sapiens 3 0.7409
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7405
Riboflavin synthase P0AFU8 RISA_ECOLI Escherichia coli 3 0.7401
Bromodomain-containing protein 2 P25440 BRD2_HUMAN Homo sapiens 3 0.7396
Non-receptor tyrosine-protein kinase TYK2 P29597 TYK2_HUMAN Homo sapiens 3 0.7394
Non-receptor tyrosine-protein kinase TYK2 P29597 TYK2_HUMAN Homo sapiens 3 0.7392
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 3 0.7388
Gag-Pol polyprotein P03367 POL_HV1BR Human immunodeficiency virus type 1 group M subtype B 3 0.7377
NADPH-dependent oxidoreductase 2-alkenal reductase Q39172 AER_ARATH Arabidopsis thaliana 3 0.7359
Mitogen-activated protein kinase 14 Q16539 MK14_HUMAN Homo sapiens 3 0.7358
Lethal factor P15917 LEF_BACAN Bacillus anthracis 3 0.7352
UDP-N-acetylmuramoyl-tripeptide--D-alanyl-D-alanine ligase Q8DNV6 Q8DNV6_STRR6 Streptococcus pneumoniae 3 0.7344
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7342
Tau-tubulin kinase 1 Q5TCY1 TTBK1_HUMAN Homo sapiens 4 0.7340
Pteridine reductase 1 Q01782 PTR1_LEIMA Leishmania major 3 0.7340
Catechol O-methyltransferase P22734 COMT_RAT Rattus norvegicus 3 0.7333
Kinesin-like protein KIF11 P52732 KIF11_HUMAN Homo sapiens 3 0.7319
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7313
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7313
FMN-dependent NAD(P)H:quinone oxidoreductase 1 Q9I5F3 AZOR1_PSEAE Pseudomonas aeruginosa 2 0.7310
Polymerase acidic protein C3W5S0 C3W5S0_I09A0 Influenza A virus 2 0.7304
Methylmalonyl-CoA decarboxylase P52045 SCPB_ECOLI Escherichia coli 3 0.7298
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.7287
Casein kinase I isoform gamma-3 Q9Y6M4 KC1G3_HUMAN Homo sapiens 3 0.7258
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7252
HTH-type transcriptional regulator QacR P0A0N4 QACR_STAAU Staphylococcus aureus 2 0.7246
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7241
Chitinase Q54276 Q54276_SERMA Serratia marcescens 3 0.7237
Angiotensin-converting enzyme 2 Q9BYF1 ACE2_HUMAN Homo sapiens 2 0.7236
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7235
Beta-galactoside-specific lectin 4 Q6ITZ3 ML4_VISAL Viscum album 2 0.7230
WxcM-like protein Q12KT8 Q12KT8_SHEDO Shewanella denitrificans 3 0.7220
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7213
CREB-binding protein Q92793 CBP_HUMAN Homo sapiens 3 0.7206
Abscisic acid receptor PYL2 O80992 PYL2_ARATH Arabidopsis thaliana 3 0.7204
Mitochondrial poly(A) polymerase F1NBW0 F1NBW0_CHICK Gallus gallus 2 0.7200
Capsid protein Q9WBP8 Q9WBP8_9VIRU Adeno-associated virus - 1 2 0.7200
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.7194
Cytohesin-2 Q99418 CYH2_HUMAN Homo sapiens 3 0.7182
Phenylalanine-4-hydroxylase P00439 PH4H_HUMAN Homo sapiens 3 0.7178
Beta-glucuronidase P05804 BGLR_ECOLI Escherichia coli 3 0.7177
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.7173
Phosphatidylinositol 5-phosphate 4-kinase type-2 beta P78356 PI42B_HUMAN Homo sapiens 3 0.7163
Serine/threonine-protein kinase SKY1 Q03656 SKY1_YEAST Saccharomyces cerevisiae 2 0.7140
Nitric oxide synthase oxygenase O34453 NOSO_BACSU Bacillus subtilis 3 0.7126
N-terminal acetyltransferase A complex subunit NAT1 P12945 NAT1_YEAST Saccharomyces cerevisiae 2 0.7112
Cyclin-dependent kinase 9 P50750 CDK9_HUMAN Homo sapiens 3 0.7109
[LysW]-aminoadipate kinase O50147 LYSZ_THET2 Thermus thermophilus 3 0.7105
Dihydrofolate reductase P0ABQ4 DYR_ECOLI Escherichia coli 3 0.7100
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.7092
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7092
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7085
Serine/threonine-protein kinase 24 Q9Y6E0 STK24_HUMAN Homo sapiens 3 0.7082
Flavin-dependent monooxygenase Q93L51 TETX_BACT4 Bacteroides thetaiotaomicron 2 0.7079
dTDP-4-dehydrorhamnose 3,5-epimerase A0A6L7H6N0 A0A1S0QLH9_BACAN Bacillus anthracis 3 0.7076
Cytidine and deoxycytidylate deaminase zinc-binding region Q82Y41 Q82Y41_NITEU Nitrosomonas europaea 2 0.7074
Beta-lactamase Q9L5C8 Q9L5C8_ECOLX Escherichia coli 3 0.7071
2',3'-cyclic-nucleotide 3'-phosphodiesterase P16330 CN37_MOUSE Mus musculus 2 0.7071
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 2 0.7069
Hypoxanthine-guanine phosphoribosyltransferase P00492 HPRT_HUMAN Homo sapiens 3 0.7052
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7051
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7036
Homoserine dehydrogenase P31116 DHOM_YEAST Saccharomyces cerevisiae 3 0.7026
Adenylosuccinate synthetase isozyme 1 P28650 PURA1_MOUSE Mus musculus 4 0.7024
Caspase-3 P42574 CASP3_HUMAN Homo sapiens 3 0.7017
HTH-type transcriptional regulator TtgR Q9AIU0 TTGR_PSEPT Pseudomonas putida 3 0.7016
Tyrosine-protein kinase JAK3 P52333 JAK3_HUMAN Homo sapiens 4 0.7013
Ethylene receptor 1 P49333 ETR1_ARATH Arabidopsis thaliana 3 0.7009
Thermolysin P00800 THER_BACTH Bacillus thermoproteolyticus 2 0.7008
Proto-oncogene tyrosine-protein kinase Src P00523 SRC_CHICK Gallus gallus 3 0.7007
Cyclic GMP-AMP phosphodiesterase SMPDL3A Q92484 ASM3A_HUMAN Homo sapiens 2 0.7001

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