(7S,8R)-5-methoxy-4-(O-beta-D-glucopyranosyl) dehydrodiconiferyl alcohol - Compound Card

(7S,8R)-5-methoxy-4-(O-beta-D-glucopyranosyl) dehydrodiconiferyl alcohol

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(7S,8R)-5-methoxy-4-(O-beta-D-glucopyranosyl) dehydrodiconiferyl alcohol

Structure
Zoomed Structure
  • Family: Plantae - Lamiaceae
  • Kingdom: Plantae
  • Class: Lignan
    • Subclass: Lignan Glycoside
Canonical Smiles OC/C=C/c1cc(OC)c2c(c1)[C@H](CO)[C@H](O2)c1cc(OC)c(c(c1)OC)O[C@@H]1O[C@H](CO)[C@H]([C@@H]([C@H]1O)O)O
InChI InChI=1S/C27H34O12/c1-34-17-8-13(5-4-6-28)7-15-16(11-29)24(38-25(15)17)14-9-18(35-2)26(19(10-14)36-3)39-27-23(33)22(32)21(31)20(12-30)37-27/h4-5,7-10,16,20-24,27-33H,6,11-12H2,1-3H3/b5-4+/t16-,20+,21+,22-,23+,24+,27-/m0/s1
InChIKey MQDDAWSOEYTMBZ-ZSEFKQENSA-N
Formula C27H34O12
HBA 12
HBD 6
MW 550.56
Rotatable Bonds 10
TPSA 176.76
LogP 0.11
Number Rings 4
Number Aromatic Rings 2
Heavy Atom Count 39
Formal Charge 0
Fraction CSP3 0.48
Exact Mass 550.21
Number of Lipinski Rule Violations 3
# Species Family Kingdom NCBI Taxonomy ID
1 Teucrium polium Lamiaceae Plantae 1117157

Showing of synonyms

  • Elmasri W.A, Yang T, et al. (2015). Teucrium polium phenylethanol and iridoid glycoside characterization and flavonoid inhibition of biofilm-forming Staphylococcus aureus. Journal of natural products, 2015, 78(1), 2-9. [View] [PubMed]
Pubchem: 101705429
Nmrshiftdb2: 60070056

No compound-protein relationship available.

Structure

SMILES: c1cccc(c12)OC(C2)c3ccc(cc3)OC4CCCCO4

Level: 2

Mol. Weight: 550.56 g/mol

Structure

SMILES: c1cccc(c12)OC(C2)c3ccccc3

Level: 1

Mol. Weight: 550.56 g/mol

Structure

SMILES: c1ccccc1OC2CCCCO2

Level: 1

Mol. Weight: 550.56 g/mol

Structure

SMILES: C1COc(c12)cccc2

Level: 0

Mol. Weight: 550.56 g/mol

Structure

SMILES: C1CCOCC1

Level: 0

Mol. Weight: 550.56 g/mol

Structure

SMILES: c1ccccc1

Level: 0

Mol. Weight: 550.56 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-6.3
Human Oral Bioavailability 20%
Non-Bioavailable
Human Intestinal Absorption
Non-Absorbed
Madin-Darby Canine Kidney
-4.91
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Substrate
Skin Permeability
0.48

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
0.97
Plasma Protein Binding
81.15
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
5.73
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-1.53
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.61
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
5.15
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
-3004.9
Rat (Acute)
2.49
Rat (Chronic Oral)
4.1
Fathead Minnow
10.56
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
512.72
Hydration Free Energy
-2.94
Log(D) at pH=7.4
0.61
Log(P)
-0.77
Log S
-3.7
Log(Vapor Pressure)
-10.51
Melting Point
191.51
pKa Acid
6.84
pKa Basic
0.83
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.8922
Stromelysin-1 P08254 MMP3_HUMAN Homo sapiens 3 0.8414
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 4 0.8400
Protein ppBat Q8A8A4 Q8A8A4_BACTN Bacteroides thetaiotaomicron VPI-5482 3 0.8307
Glucan 1,3-beta-glucosidase P29717 EXG1_CANAL Candida albicans 3 0.8288
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.8210
Mycocyclosin synthase P9WPP7 CP121_MYCTU Mycobacterium tuberculosis 3 0.8140
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.7945
GCN5-related N-acetyltransferase B1YEL6 B1YEL6_EXIS2 Exiguobacterium sibiricum 3 0.7933
GCN5-related N-acetyltransferase B1YEL6 B1YEL6_EXIS2 Exiguobacterium sibiricum 3 0.7895
S-adenosylmethionine decarboxylase proenzyme P17707 DCAM_HUMAN Homo sapiens 3 0.7722
Serpin domain-containing protein H0ZQY2 H0ZQY2_TAEGU Taeniopygia guttata 3 0.7719
beta-glucosidase Q92AS9 Q92AS9_LISIN Listeria innocua serovar 6a 3 0.7718
5-methylthioadenosine/S-adenosylhomocysteine deaminase Q7NZ90 Q7NZ90_CHRVO Chromobacterium violaceum 3 0.7708
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 4 0.7645
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7574
Purine nucleoside phosphorylase DeoD-type P0ABP9 DEOD_ECO57 Escherichia coli O157:H7 3 0.7533
Genome polyprotein P26663 POLG_HCVBK Hepatitis C virus genotype 1b 3 0.7436
Serine/threonine-protein kinase Chk2 O96017 CHK2_HUMAN Homo sapiens 3 0.7397
Bromodomain-containing protein 2 P25440 BRD2_HUMAN Homo sapiens 3 0.7378
Endothiapepsin P11838 CARP_CRYPA Cryphonectria parasitica 3 0.7352
2',3'-cyclic-nucleotide 3'-phosphodiesterase P16330 CN37_MOUSE Mus musculus 3 0.7304
Polyribonucleotide nucleotidyltransferase A7ZS61 PNP_ECO24 Escherichia coli O139:H28 3 0.7287
Cytosolic purine 5'-nucleotidase P49902 5NTC_HUMAN Homo sapiens 2 0.7215
Vascular endothelial growth factor receptor 2 P35968 VGFR2_HUMAN Homo sapiens 3 0.7189
Maltose/maltodextrin-binding periplasmic protein P0AEX9 MALE_ECOLI Escherichia coli 3 0.7117
Flavin-dependent monooxygenase Q93L51 TETX_BACT4 Bacteroides thetaiotaomicron 3 0.7068
Beta-glucuronidase P05804 BGLR_ECOLI Escherichia coli 3 0.7062
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7058
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7036
Elongation factor Tu 1 P0CE47 EFTU1_ECOLI Escherichia coli 3 0.7019
Gag-Pol polyprotein P05896 POL_SIVM1 Simian immunodeficiency virus 3 0.7008
Mitochondrial poly(A) polymerase F1NBW0 F1NBW0_CHICK Gallus gallus 2 0.7002
Nucleoside 2-deoxyribosyltransferase Q8RLY5 Q8RLY5_LACHE Lactobacillus helveticus 2 0.7001

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