Lariciresinol-4''-O-beta-D-glucopyranoside - Compound Card

Lariciresinol-4''-O-beta-D-glucopyranoside

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Lariciresinol-4''-O-beta-D-glucopyranoside

Structure
Zoomed Structure
  • Family: Plantae - Thymelaeaceae
  • Kingdom: Plantae
  • Class: Lignan
    • Subclass: Lignan Glycoside
Canonical Smiles OCC1C(OC[C@@H]1c1ccc(c(c1)O)OC)Cc1ccc(c(c1)OC)O[C@@H]1O[C@H](CO)[C@H]([C@@H]([C@H]1O)O)O
InChI InChI=1S/C26H34O11/c1-33-18-6-4-14(9-17(18)29)16-12-35-20(15(16)10-27)7-13-3-5-19(21(8-13)34-2)36-26-25(32)24(31)23(30)22(11-28)37-26/h3-6,8-9,15-16,20,22-32H,7,10-12H2,1-2H3/t15?,16-,20?,22-,23-,24+,25-,26-/m1/s1
InChIKey SLGRWIAOGFTNGR-YGXHAFSUSA-N
Formula C26H34O11
HBA 11
HBD 6
MW 522.55
Rotatable Bonds 9
TPSA 167.53
LogP -0.08
Number Rings 4
Number Aromatic Rings 2
Heavy Atom Count 37
Formal Charge 0
Fraction CSP3 0.54
Exact Mass 522.21
Number of Lipinski Rule Violations 3
# Species Family Kingdom NCBI Taxonomy ID
1 Thymelaea microphylla Thymelaeaceae Plantae 224056

Showing of synonyms

  • Kerbab K, Mekhelfi T, et al. (2015). Chemical composition and antioxidant activity of a polar extract of Thymelaea microphylla Coss. Et Dur. Nat Prod Res,2015,29(7),671-5. [View] [PubMed]

No compound-protein relationship available.

Structure

SMILES: c1ccccc1C(CO2)CC2Cc3ccc(cc3)OC4CCCCO4

Level: 3

Mol. Weight: 522.55 g/mol

Structure

SMILES: O1CCCC1Cc2ccc(cc2)OC3CCCCO3

Level: 2

Mol. Weight: 522.55 g/mol

Structure

SMILES: c1ccccc1CC2CC(CO2)c3ccccc3

Level: 2

Mol. Weight: 522.55 g/mol

Structure

SMILES: c1ccccc1OC2CCCCO2

Level: 1

Mol. Weight: 522.55 g/mol

Structure

SMILES: O1CCCC1Cc2ccccc2

Level: 1

Mol. Weight: 522.55 g/mol

Structure

SMILES: C1OCCC1c2ccccc2

Level: 1

Mol. Weight: 522.55 g/mol

Structure

SMILES: C1CCOCC1

Level: 0

Mol. Weight: 522.55 g/mol

Structure

SMILES: c1ccccc1

Level: 0

Mol. Weight: 522.55 g/mol

Structure

SMILES: C1CCOC1

Level: 0

Mol. Weight: 522.55 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-6.53
Human Oral Bioavailability 20%
Non-Bioavailable
Human Intestinal Absorption
Non-Absorbed
Madin-Darby Canine Kidney
-5.04
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Substrate
Skin Permeability
-0.34

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
0.92
Plasma Protein Binding
74.49
Steady State Volume of Distribution
-

Metabolism

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

Excretion

Clearance
10.86
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-1.81
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.52
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
5.03
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
-1189.95
Rat (Acute)
2.48
Rat (Chronic Oral)
3.93
Fathead Minnow
4.97
Respiratory Disease
Safe
Skin Sensitisation
Safe
SR-ARE
Safe
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Safe

General Properties

Boiling Point
523.15
Hydration Free Energy
-2.96
Log(D) at pH=7.4
1.1
Log(P)
-0.42
Log S
-3.63
Log(Vapor Pressure)
-11.07
Melting Point
198.42
pKa Acid
6.11
pKa Basic
3.92
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 0.9378
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.9311
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.9266
rRNA N-glycosylase D9J2T9 D9J2T9_MOMBA Momordica balsamina 3 0.9183
Thymidine phosphorylase Q7CP66 TYPH_SALTY Salmonella typhimurium 3 0.9139
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 3 0.9022
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.8946
NAD(P)H-hydrate epimerase Q8K4Z3 NNRE_MOUSE Mus musculus 3 0.8884
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8857
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 3 0.8833
MAP kinase-activated protein kinase 2 P49137 MAPK2_HUMAN Homo sapiens 3 0.8726
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 3 0.8700
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.8679
Flavin-dependent monooxygenase Q93L51 TETX_BACT4 Bacteroides thetaiotaomicron 3 0.8637
DNA gyrase subunit A P0AES5 GYRA_SHIFL Shigella flexneri 3 0.8489
Purine nucleoside phosphorylase DeoD-type P0ABP9 DEOD_ECO57 Escherichia coli O157:H7 3 0.8472
Phenylalanine-4-hydroxylase P00439 PH4H_HUMAN Homo sapiens 3 0.8453
Glucan 1,3-beta-glucosidase P29717 EXG1_CANAL Candida albicans 3 0.8431
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 3 0.8369
Biflaviolin synthase CYP158A1 Q9KZF5 C1581_STRCO Streptomyces coelicolor / M145) 3 0.8363
Mitogen-activated protein kinase 14 Q16539 MK14_HUMAN Homo sapiens 3 0.8350
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.8306
Protein mono-ADP-ribosyltransferase PARP3 Q9Y6F1 PARP3_HUMAN Homo sapiens 3 0.8289
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.8260
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.8210
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.8204
Serpin domain-containing protein H0ZQY2 H0ZQY2_TAEGU Taeniopygia guttata 3 0.8102
Acetolactate synthase, chloroplastic P17597 ILVB_ARATH Arabidopsis thaliana 3 0.8063
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.8062
cAMP-dependent protein kinase catalytic subunit alpha P00517 KAPCA_BOVIN Bos taurus 3 0.8060
Mitogen-activated protein kinase 1 P28482 MK01_HUMAN Homo sapiens 3 0.8049
Pteridine reductase 1 Q01782 PTR1_LEIMA Leishmania major 3 0.8043
Raucaffricine-O-beta-D-glucosidase Q9SPP9 RG1_RAUSE Rauvolfia serpentina 4 0.8038
2',3'-cyclic-nucleotide 3'-phosphodiesterase P16330 CN37_MOUSE Mus musculus 3 0.8035
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.8023
Urokinase-type plasminogen activator P00749 UROK_HUMAN Homo sapiens 3 0.8012
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.8006
Dual specificity mitogen-activated protein kinase kinase 1 Q02750 MP2K1_HUMAN Homo sapiens 3 0.7976
Hypoxanthine phosphoribosyltransferase Q4DRC4 Q4DRC4_TRYCC Trypanosoma cruzi 3 0.7951
11-beta-hydroxysteroid dehydrogenase 1 P28845 DHI1_HUMAN Homo sapiens 3 0.7911
Mitogen-activated protein kinase 8 P45983 MK08_HUMAN Homo sapiens 3 0.7835
Peptidyl-prolyl cis-trans isomerase FKBP1A P62942 FKB1A_HUMAN Homo sapiens 3 0.7828
Hepatocyte growth factor receptor P08581 MET_HUMAN Homo sapiens 3 0.7808
Metallophosphoesterase MPPED2 B1WBP0 MPPD2_RAT Rattus norvegicus 4 0.7804
beta-glucosidase Q92AS9 Q92AS9_LISIN Listeria innocua serovar 6a 3 0.7797
Nuclear receptor subfamily 4immunitygroup A member 1 P22736 NR4A1_HUMAN Homo sapiens 3 0.7786
Acetolactate synthase, chloroplastic P17597 ILVB_ARATH Arabidopsis thaliana 3 0.7779
Ribonuclease J H9CZL7 H9CZL7_DEIRD Deinococcus radiodurans 3 0.7770
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7722
Polyribonucleotide nucleotidyltransferase A7ZS61 PNP_ECO24 Escherichia coli O139:H28 3 0.7673
Seminal ribonuclease P00669 RNS_BOVIN Bos taurus 3 0.7664
2-aminohexano-6-lactam racemase Q7M181 ACLR_ACHOB Achromobacter obae 3 0.7649
Gag-Pol polyprotein P03367 POL_HV1BR Human immunodeficiency virus type 1 group M subtype B 3 0.7634
Sulfide-quinone reductase B7JBP8 SQRD_ACIF2 Acidithiobacillus ferrooxidans) 3 0.7614
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.7568
Glucan 1,3-beta-glucosidase P29717 EXG1_CANAL Candida albicans 3 0.7565
Prolyl tripeptidyl peptidase Q7MUW6 PTP_PORGI Porphyromonas gingivalis 3 0.7552
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7526
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7521
cGMP-dependent protein kinase 1 P00516 KGP1_BOVIN Bos taurus 3 0.7520
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7518
Carnitine O-palmitoyltransferase 2, mitochondrial P18886 CPT2_RAT Rattus norvegicus 3 0.7515
Nickel-binding periplasmic protein P33590 NIKA_ECOLI Escherichia coli 2 0.7507
Endothiapepsin P11838 CARP_CRYPA Cryphonectria parasitica 3 0.7493
Vascular endothelial growth factor receptor 2 P35968 VGFR2_HUMAN Homo sapiens 3 0.7493
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7488
Transcriptional regulator, PadR-like family A2RI36 A2RI36_LACLM Lactococcus lactis subsp. cremoris 3 0.7488
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 3 0.7488
APH(2'')-Id O68183 O68183_ENTCA Enterococcus casseliflavus 3 0.7485
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase Q05603 COBT_SALTY Salmonella typhimurium 2 0.7478
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform P48736 PK3CG_HUMAN Homo sapiens 3 0.7474
Gag-Pol polyprotein P12497 POL_HV1N5 Human immunodeficiency virus type 1 group M subtype B 3 0.7463
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7448
Nucleoside diphosphate kinase A 2 P52175 NDKA2_BOVIN Bos taurus 3 0.7425
ALK tyrosine kinase receptor Q9UM73 ALK_HUMAN Homo sapiens 3 0.7424
Interstitial collagenase P03956 MMP1_HUMAN Homo sapiens 3 0.7420
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7418
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7406
Purine nucleoside phosphorylase DeoD-type P0ABP9 DEOD_ECO57 Escherichia coli O157:H7 3 0.7403
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7394
Beta-galactoside-specific lectin 1 P81446 ML1_VISAL Viscum album 3 0.7381
Bifunctional epoxide hydrolase 2 P34913 HYES_HUMAN Homo sapiens 2 0.7377
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7369
5-methylthioadenosine/S-adenosylhomocysteine deaminase Q7NZ90 Q7NZ90_CHRVO Chromobacterium violaceum 3 0.7368
N-acetyltransferase domain-containing protein Q9HV14 Q9HV14_PSEAE Pseudomonas aeruginosa 3 0.7359
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 3 0.7344
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.7340
Histone deacetylase 4 P56524 HDAC4_HUMAN Homo sapiens 3 0.7293
Regucalcin Q64374 RGN_MOUSE Mus musculus 3 0.7291
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7290
Polymerase acidic protein C3W5S0 C3W5S0_I09A0 Influenza A virus 2 0.7284
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7281
Pancreatic alpha-amylase P04746 AMYP_HUMAN Homo sapiens 2 0.7277
Purine nucleoside phosphorylase 2 P45563 XAPA_ECOLI Escherichia coli 3 0.7261
Mitochondrial poly(A) polymerase F1NBW0 F1NBW0_CHICK Gallus gallus 2 0.7252
Catechol O-methyltransferase P22734 COMT_RAT Rattus norvegicus 3 0.7246
3-hydroxyanthranilate 3,4-dioxygenase Q1LCS4 3HAO_CUPMC Cupriavidus metallidurans 2 0.7237
Bromodomain-containing protein 2 P25440 BRD2_HUMAN Homo sapiens 3 0.7236
Urokinase-type plasminogen activator P00749 UROK_HUMAN Homo sapiens 2 0.7234
Pheromone-binding protein ASP1 Q9U9J6 Q9U9J6_APIME Apis mellifera 3 0.7233
UDP-galactopyranose mutase Q48485 GLF1_KLEPN Klebsiella pneumoniae 3 0.7221
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.7217
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 3 0.7197
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.7196
Histone-lysine N-methyltransferase SETD7 Q8WTS6 SETD7_HUMAN Homo sapiens 3 0.7195
Phosphatidylinositol 5-phosphate 4-kinase type-2 beta P78356 PI42B_HUMAN Homo sapiens 3 0.7189
Gag-Pol polyprotein P05896 POL_SIVM1 Simian immunodeficiency virus 3 0.7184
Gag-Pol polyprotein P03369 POL_HV1A2 Human immunodeficiency virus type 1 group M subtype B 3 0.7170
Proto-oncogene tyrosine-protein kinase Src P00523 SRC_CHICK Gallus gallus 2 0.7168
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase Q05603 COBT_SALTY Salmonella typhimurium 2 0.7168
Beta-galactoside-specific lectin 4 Q6ITZ3 ML4_VISAL Viscum album 2 0.7167
Dihydropteroate synthase Q81VW8 Q81VW8_BACAN Bacillus anthracis 2 0.7162
Putative S-adenosyl-L-methionine-dependent methyltransferase ML2640 Q9CCZ4 Y2640_MYCLE Mycobacterium leprae 3 0.7161
Hypoxanthine-guanine phosphoribosyltransferase P00492 HPRT_HUMAN Homo sapiens 3 0.7158
Gag-Pol polyprotein P12497 POL_HV1N5 Human immunodeficiency virus type 1 group M subtype B 2 0.7146
GTP 3',8-cyclase P69848 MOAA_STAA8 Staphylococcus aureus 3 0.7144
Annexin A5 P08758 ANXA5_HUMAN Homo sapiens 2 0.7134
Non-receptor tyrosine-protein kinase TYK2 P29597 TYK2_HUMAN Homo sapiens 4 0.7127
tRNA (adenine(9)-N1)-methyltransferase Q4J894 TRM10_SULAC Sulfolobus acidocaldarius 3 0.7126
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7119
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7115
Hypoxanthine-guanine phosphoribosyltransferase P00492 HPRT_HUMAN Homo sapiens 3 0.7113
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7102
Botulinum neurotoxin type B P10844 BXB_CLOBO Clostridium botulinum 3 0.7095
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7093
Gag-Pol polyprotein P04584 POL_HV2RO Human immunodeficiency virus type 2 subtype A 3 0.7088
dTDP-4-dehydrorhamnose 3,5-epimerase A0A6L7H6N0 A0A1S0QLH9_BACAN Bacillus anthracis 3 0.7085
Hypoxanthine-guanine phosphoribosyltransferase P00492 HPRT_HUMAN Homo sapiens 3 0.7083
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 2 0.7083
Phenylalanine-4-hydroxylase P00439 PH4H_HUMAN Homo sapiens 3 0.7078
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7077
Deoxycytidine kinase P27707 DCK_HUMAN Homo sapiens 4 0.7074
5'-methylthioadenosine/S-adenosylhomocysteine nucleosidase Q81LL4 MTNN_BACAN Bacillus anthracis 2 0.7074
Macrophage colony-stimulating factor 1 receptor P07333 CSF1R_HUMAN Homo sapiens 3 0.7067
Genome polyprotein P26663 POLG_HCVBK Hepatitis C virus genotype 1b 3 0.7067
Ribosomal small subunit pseudouridine synthase A P0AA43 RSUA_ECOLI Escherichia coli 2 0.7063
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7044
ALK tyrosine kinase receptor Q9UM73 ALK_HUMAN Homo sapiens 3 0.7033
Ribosomal small subunit pseudouridine synthase A P0AA43 RSUA_ECOLI Escherichia coli 3 0.7032
ALK tyrosine kinase receptor Q9UM73 ALK_HUMAN Homo sapiens 3 0.7023
Glucose-1-phosphate thymidylyltransferase Q9HU22 Q9HU22_PSEAE Pseudomonas aeruginosa 3 0.7018
Phosphatidylinositol 5-phosphate 4-kinase type-2 beta P78356 PI42B_HUMAN Homo sapiens 4 0.7013
Proto-oncogene tyrosine-protein kinase receptor Ret P07949 RET_HUMAN Homo sapiens 3 0.7011
GCN5-related N-acetyltransferase B1YEL6 B1YEL6_EXIS2 Exiguobacterium sibiricum 3 0.7006

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