Dehydro-diconiferyl alcohol 4-O-beta-D-glucoside - Compound Card

Dehydro-diconiferyl alcohol 4-O-beta-D-glucoside

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Dehydro-diconiferyl alcohol 4-O-beta-D-glucoside

Structure
Zoomed Structure
  • Family: Plantae - Rubiaceae
  • Kingdom: Plantae
  • Class: Lignan
Canonical Smiles OC/C=C/c1cc(OC)c2c(c1)[C@@](C)(CO)[C@](O2)(C)c1ccc(c(c1)OC)O[C@@H]1O[C@H](CO)[C@H]([C@@H]([C@H]1O)O)O
InChI InChI=1S/C28H36O11/c1-27(14-31)17-10-15(6-5-9-29)11-20(36-4)25(17)39-28(27,2)16-7-8-18(19(12-16)35-3)37-26-24(34)23(33)22(32)21(13-30)38-26/h5-8,10-12,21-24,26,29-34H,9,13-14H2,1-4H3/b6-5+/t21-,22-,23+,24-,26-,27-,28+/m1/s1
InChIKey VHGYFWFDUYCPNE-KRXXYROUSA-N
Formula C28H36O11
HBA 11
HBD 6
MW 548.59
Rotatable Bonds 9
TPSA 167.53
LogP 0.45
Number Rings 4
Number Aromatic Rings 2
Heavy Atom Count 39
Formal Charge 0
Fraction CSP3 0.5
Exact Mass 548.23
Number of Lipinski Rule Violations 3
# Species Family Kingdom NCBI Taxonomy ID
1 Galium brunneum Rubiaceae Plantae 25168

Showing of synonyms

  • Smadi A, Bitam F, et al. (2020). Chemical constituents of the aerial parts of Algerian Galium brunneum:Isolation of new hydroperoxy sterol glucosyl derivatives. Phytochemistry Letters, 2020, 38, 39-45. [View]

No compound-protein relationship available.

Structure

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

Level: 2

Mol. Weight: 548.59 g/mol

Structure

SMILES: c1cccc(c12)OC(C2)c3ccccc3

Level: 1

Mol. Weight: 548.59 g/mol

Structure

SMILES: c1ccccc1OC2CCCCO2

Level: 1

Mol. Weight: 548.59 g/mol

Structure

SMILES: C1COc(c12)cccc2

Level: 0

Mol. Weight: 548.59 g/mol

Structure

SMILES: C1CCOCC1

Level: 0

Mol. Weight: 548.59 g/mol

Structure

SMILES: c1ccccc1

Level: 0

Mol. Weight: 548.59 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-6.31
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
0.03

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
1.02
Plasma Protein Binding
91.84
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
6.42
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-1.66
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.56
Liver Injury II
Toxic
hERG Blockers
Toxic
Daphnia Maga
5.12
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
-2261.02
Rat (Acute)
2.7
Rat (Chronic Oral)
3.94
Fathead Minnow
9.5
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
521.39
Hydration Free Energy
-2.95
Log(D) at pH=7.4
1.23
Log(P)
-0.21
Log S
-3.69
Log(Vapor Pressure)
-10.47
Melting Point
192.94
pKa Acid
7.04
pKa Basic
2.46
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 0.9047
Flavin-dependent monooxygenase Q93L51 TETX_BACT4 Bacteroides thetaiotaomicron 3 0.8812
Probable NDP-rhamnosyltransferase Q9ALM8 Q9ALM8_SACSN Saccharopolyspora spinosa 3 0.8314
2',3'-cyclic-nucleotide 3'-phosphodiesterase P16330 CN37_MOUSE Mus musculus 3 0.8229
Serpin domain-containing protein H0ZQY2 H0ZQY2_TAEGU Taeniopygia guttata 3 0.7985
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.7881
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.7857
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 3 0.7833
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7826
beta-glucosidase Q92AS9 Q92AS9_LISIN Listeria innocua serovar 6a 3 0.7821
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.7810
NADPH dehydrogenase 1 Q02899 OYE1_SACPS Saccharomyces pastorianus 3 0.7583
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.7517
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7515
Thymidylate synthase P00469 TYSY_LACCA Lacticaseibacillus casei 3 0.7459
Polyribonucleotide nucleotidyltransferase A7ZS61 PNP_ECO24 Escherichia coli O139:H28 3 0.7368
Lethal(3)malignant brain tumor-like protein 1 Q9Y468 LMBL1_HUMAN Homo sapiens 3 0.7356
GTP 3',8-cyclase P69848 MOAA_STAA8 Staphylococcus aureus 3 0.7354
Stromelysin-1 P08254 MMP3_HUMAN Homo sapiens 3 0.7226
Nuclear receptor subfamily 4immunitygroup A member 1 P22736 NR4A1_HUMAN Homo sapiens 3 0.7221
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7187
S-adenosylmethionine decarboxylase proenzyme P17707 DCAM_HUMAN Homo sapiens 3 0.7172
Aldos-2-ulose dehydratase P84193 AUD_PHACH Phanerodontia chrysosporium 3 0.7096
Pheromone-binding protein ASP1 Q9U9J6 Q9U9J6_APIME Apis mellifera 3 0.7060
Glucan 1,3-beta-glucosidase P29717 EXG1_CANAL Candida albicans 3 0.7030

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