Lithospermoside - Compound Card

Lithospermoside

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Lithospermoside

Structure
Zoomed Structure
  • Family: Plantae - Leguminosae/Fabaceae
  • Kingdom: Plantae
  • Class: Cyanoglucoside
Canonical Smiles N#C/C=C\1/C=C[C@H]([C@@H]([C@H]1O[C@@H]1O[C@H](CO)[C@H]([C@@H]([C@H]1O)O)O)O)O
InChI InChI=1S/C14H19NO8/c15-4-3-6-1-2-7(17)9(18)13(6)23-14-12(21)11(20)10(19)8(5-16)22-14/h1-3,7-14,16-21H,5H2/b6-3-/t7-,8-,9+,10-,11+,12-,13+,14+/m1/s1
InChIKey WIIDBJNWXCWLKF-VVAXPEBGSA-N
Formula C14H19NO8
HBA 9
HBD 6
MW 329.31
Rotatable Bonds 3
TPSA 163.63
LogP -3.09
Number Rings 2
Number Aromatic Rings 0
Heavy Atom Count 23
Formal Charge 0
Fraction CSP3 0.64
Exact Mass 329.11
Number of Lipinski Rule Violations 1
# Species Family Kingdom NCBI Taxonomy ID
1 Bauhinia fassoglensis Leguminosae/Fabaceae Plantae 228518

Showing of synonyms

  • Fort DM, Jolad SD, et al. (2001). Lithospermoside from Bauhinia fassoglensis (Fabaceae).. Biochemical systematics and ecology,2001, 30,29(4),439-441. [View] [PubMed]
Pubchem: 10065132
Kegg Ligand: C17771
Chebi: 81324
Nmrshiftdb2: 60067422

No compound-protein relationship available.

Structure

SMILES: C=C1C=CCCC1OC2CCCCO2

Level: 1

Mol. Weight: 329.31 g/mol

Structure

SMILES: C=C1C=CCCC1

Level: 0

Mol. Weight: 329.31 g/mol

Structure

SMILES: C1CCOCC1

Level: 0

Mol. Weight: 329.31 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-5.28
Human Oral Bioavailability 20%
Non-Bioavailable
Human Intestinal Absorption
Non-Absorbed
Madin-Darby Canine Kidney
-4.900
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-0.88

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
0.710
Plasma Protein Binding
47.97
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
Non-Substrate
OATP1B1
Non-Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
3.490
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-2.760
Biodegradation
Toxic
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
1.340
Liver Injury II
Safe
hERG Blockers
Safe
Daphnia Maga
4.370
Micronucleos
Safe
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
-6.520
Rat (Acute)
2.470
Rat (Chronic Oral)
3.390
Fathead Minnow
2.770
Respiratory Disease
Safe
Skin Sensitisation
Toxic
SR-ARE
Safe
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Safe

General Properties

Boiling Point
487.690
Hydration Free Energy
-21.370
Log(D) at pH=7.4
-1.020
Log(P)
-2.26
Log S
-0.99
Log(Vapor Pressure)
-15.16
Melting Point
150.41
pKa Acid
5.29
pKa Basic
5.01
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 3 0.8679
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 3 0.8679
Prolyl tripeptidyl peptidase Q7MUW6 PTP_PORGI Porphyromonas gingivalis 3 0.8262
Prolyl tripeptidyl peptidase Q7MUW6 PTP_PORGI Porphyromonas gingivalis 3 0.8262

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