(-)-lyoniresinol 3alpha-O-alpha-L-rhamnopyranoside - Compound Card

(-)-lyoniresinol 3alpha-O-alpha-L-rhamnopyranoside

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(-)-lyoniresinol 3alpha-O-alpha-L-rhamnopyranoside

Structure
Zoomed Structure
  • Family: Plantae - Bignoniaceae
  • Kingdom: Plantae
  • Class: Lignan
    • Subclass: Lignan Glucoside
Canonical Smiles OC[C@H]1Cc2cc(OC)c(c(c2[C@H]([C@@H]1COC1OC(C)C(C(C1O)O)O)c1cc(OC)c(c(c1)OC)O)OC)O
InChI InChI=1S/C28H38O12/c1-12-22(30)25(33)26(34)28(40-12)39-11-16-15(10-29)6-13-7-19(37-4)24(32)27(38-5)21(13)20(16)14-8-17(35-2)23(31)18(9-14)36-3/h7-9,12,15-16,20,22,25-26,28-34H,6,10-11H2,1-5H3/t12?,15-,16-,20+,22?,25?,26?,28?/m1/s1
InChIKey MVVPJSSIOPWZBQ-XSLZCOTRSA-N
Formula C28H38O12
HBA 12
HBD 6
MW 566.6
Rotatable Bonds 9
TPSA 176.76
LogP 0.89
Number Rings 4
Number Aromatic Rings 2
Heavy Atom Count 40
Formal Charge 0
Fraction CSP3 0.57
Exact Mass 566.24
Number of Lipinski Rule Violations 3
# Species Family Kingdom NCBI Taxonomy ID
1 Bignonia binata Bignoniaceae Plantae 680235

Showing of synonyms

  • Mahmoud B, Samy M, et al. (2020). Bignanoside A "A new neolignan glucoside" and bignanoside B "A new iridoid glucoside" from Bignonia binata leaves. Phytochemistry Letters, 2020, 35, 200-205. [View]

No compound-protein relationship available.

Structure

SMILES: O1CCCCC1OCC(C2c3ccccc3)CCc(c24)cccc4

Level: 2

Mol. Weight: 566.6 g/mol

Structure

SMILES: O1CCCCC1OCC(C2)CCc(c23)cccc3

Level: 1

Mol. Weight: 566.6 g/mol

Structure

SMILES: c1cccc(c12)CCCC2c3ccccc3

Level: 1

Mol. Weight: 566.6 g/mol

Structure

SMILES: C1CCCc(c12)cccc2

Level: 0

Mol. Weight: 566.6 g/mol

Structure

SMILES: C1CCOCC1

Level: 0

Mol. Weight: 566.6 g/mol

Structure

SMILES: c1ccccc1

Level: 0

Mol. Weight: 566.6 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-6.55
Human Oral Bioavailability 20%
Non-Bioavailable
Human Intestinal Absorption
Non-Absorbed
Madin-Darby Canine Kidney
-5.230
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Substrate
Skin Permeability
0.73

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
0.840
Plasma Protein Binding
42.51
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
13.820
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-1.170
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.590
Liver Injury II
Safe
hERG Blockers
Safe
Daphnia Maga
5.730
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
-3391.300
Rat (Acute)
2.440
Rat (Chronic Oral)
3.950
Fathead Minnow
12.220
Respiratory Disease
Safe
Skin Sensitisation
Safe
SR-ARE
Safe
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Toxic

General Properties

Boiling Point
491.080
Hydration Free Energy
-2.960
Log(D) at pH=7.4
0.800
Log(P)
-0.24
Log S
-3.9
Log(Vapor Pressure)
-9.03
Melting Point
173.44
pKa Acid
6.71
pKa Basic
3.47
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Bromodomain testis-specific protein Q58F21 BRDT_HUMAN Homo sapiens 3 0.8981
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.8970
ATP-dependent molecular chaperone HSP82 P02829 HSP82_YEAST Saccharomyces cerevisiae 3 0.8892
Riboflavin synthase P0AFU8 RISA_ECOLI Escherichia coli 4 0.8753
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.8750
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 3 0.8709
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.8663
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.8653
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 3 0.8538
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.8353
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.8113
Homoserine dehydrogenase P31116 DHOM_YEAST Saccharomyces cerevisiae 4 0.8063
Peptidyl-prolyl cis-trans isomerase FKBP1A P62942 FKB1A_HUMAN Homo sapiens 3 0.7881
Prolyl tripeptidyl peptidase Q7MUW6 PTP_PORGI Porphyromonas gingivalis 3 0.7871
WxcM-like protein Q12KT8 Q12KT8_SHEDO Shewanella denitrificans 4 0.7855
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 3 0.7803
NADH:flavin oxidoreductase Sye1 Q8EEC8 Q8EEC8_SHEON Shewanella oneidensis 3 0.7753
Thymidylate synthase P0A886 TYSY_ECO57 Escherichia coli O157:H7 3 0.7681
Hypoxanthine phosphoribosyltransferase Q4DRC4 Q4DRC4_TRYCC Trypanosoma cruzi 3 0.7675
RNA-dependent RNA polymerase Q6A562 Q6A562_9VIRU Thosea asigna virus 3 0.7653
Thymidylate synthase P0A884 TYSY_ECOLI Escherichia coli 4 0.7645
Serine/threonine-protein kinase 24 Q9Y6E0 STK24_HUMAN Homo sapiens 3 0.7509
S-adenosylmethionine decarboxylase proenzyme P17707 DCAM_HUMAN Homo sapiens 3 0.7410
Aldos-2-ulose dehydratase P84193 AUD_PHACH Phanerodontia chrysosporium 3 0.7350
Carbonyl reductase [NADPH] 1 P16152 CBR1_HUMAN Homo sapiens 3 0.7305
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7283
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform P48736 PK3CG_HUMAN Homo sapiens 3 0.7256
Polymerase acidic protein C3W5S0 C3W5S0_I09A0 Influenza A virus 2 0.7237
Beta-galactoside-specific lectin 4 Q6ITZ3 ML4_VISAL Viscum album 2 0.7197
Aldo-keto reductase family 1 member A1 P50578 AK1A1_PIG Sus scrofa 3 0.7194
D-aminoacyl-tRNA deacylase Q8IIS0 DTD_PLAF7 Plasmodium falciparum 3 0.7131
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.7109
Endoplasmin P41148 ENPL_CANLF Canis lupus familiaris 3 0.7053
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 2 0.7017

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