15-desoxylactucin-alpha-D-glucopyranoside - Compound Card

15-desoxylactucin-alpha-D-glucopyranoside

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15-desoxylactucin-alpha-D-glucopyranoside

Structure
Zoomed Structure
  • Family: Plantae - Asteraceae
  • Kingdom: Plantae
  • Class: Terpenoid
    • Subclass: Sesquiterpene Glycoside
Canonical Smiles OC[C@H]1O[C@@H](O[C@H]2CC(=C3[C@@H]([C@@H]4[C@@H]2C(=C)C(=O)O4)C(=CC3=O)C)C)[C@@H]([C@H]([C@@H]1O)O)O
InChI InChI=1S/C21H26O9/c1-7-4-10(23)13-8(2)5-11(15-9(3)20(27)30-19(15)14(7)13)28-21-18(26)17(25)16(24)12(6-22)29-21/h4,11-12,14-19,21-22,24-26H,3,5-6H2,1-2H3/t11-,12+,14-,15+,16+,17-,18+,19+,21+/m0/s1
InChIKey FYHUGBDJWHPAHG-ZOHFHJANSA-N
Formula C21H26O9
HBA 9
HBD 4
MW 422.43
Rotatable Bonds 3
TPSA 142.75
LogP -0.87
Number Rings 4
Number Aromatic Rings 0
Heavy Atom Count 30
Formal Charge 0
Fraction CSP3 0.62
Exact Mass 422.16
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Reichardia tingitana Asteraceae Plantae 43208

Showing of synonyms

  • Abdel-Mogib M, Awad SN, et al. (1993). A sesquiterpene glucoside from Reichardia tingitana. Phytochemistry,1993,34(5),1434-1435. [View]
Pubchem: 24066905
Nmrshiftdb2: 70028334

No compound-protein relationship available.

Structure

SMILES: O=C1C=CC(C1=2)C3C(C(=C)C(=O)O3)C(CC2)OC4CCCCO4

Level: 1

Mol. Weight: 422.43 g/mol

Structure

SMILES: C1CCC(C(=C)C(=O)O2)C2C(C=13)C=CC3=O

Level: 0

Mol. Weight: 422.43 g/mol

Structure

SMILES: C1CCOCC1

Level: 0

Mol. Weight: 422.43 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-5.36
Human Oral Bioavailability 20%
Non-Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.880
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Substrate
Skin Permeability
-1.69

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
0.770
Plasma Protein Binding
64.06
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
Inhibitor
CYP 2D6 Substrate
Non-Substrate
CYP 3A4 Inhibitor
Non-Inhibitor
CYP 3A4 Substrate
Non-Substrate
OATP1B1
Non-Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
5.020
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-2.900
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.550
Liver Injury II
Safe
hERG Blockers
Safe
Daphnia Maga
4.870
Micronucleos
Toxic
NR-AhR
Safe
NR-AR
Safe
NR-AR-LBD
Toxic
NR-Aromatase
Safe
NR-ER
Safe
NR-ER-LBD
Safe
NR-GR
Toxic
NR-PPAR-gamma
Safe
NR-TR
Safe
T. Pyriformis
-29.550
Rat (Acute)
3.450
Rat (Chronic Oral)
3.280
Fathead Minnow
4.020
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
490.470
Hydration Free Energy
-6.940
Log(D) at pH=7.4
0.560
Log(P)
-1.01
Log S
-1.85
Log(Vapor Pressure)
-12.61
Melting Point
186.53
pKa Acid
5.36
pKa Basic
5.13
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Serpin domain-containing protein H0ZQY2 H0ZQY2_TAEGU Taeniopygia guttata 3 0.8730
Serpin domain-containing protein H0ZQY2 H0ZQY2_TAEGU Taeniopygia guttata 3 0.8730
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.8250
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.8250
Raucaffricine-O-beta-D-glucosidase Q9SPP9 RG1_RAUSE Rauvolfia serpentina 4 0.7211
Raucaffricine-O-beta-D-glucosidase Q9SPP9 RG1_RAUSE Rauvolfia serpentina 4 0.7211

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