3beta,14-dihydroxycostunolide-3-O-beta-glycopyranoside - Compound Card

3beta,14-dihydroxycostunolide-3-O-beta-glycopyranoside

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3beta,14-dihydroxycostunolide-3-O-beta-glycopyranoside

Structure
Zoomed Structure
  • Family: Plantae - Asteraceae
  • Kingdom: Plantae
  • Class: Terpenoid
    • Subclass: Sesquiterpene Lactone
Canonical Smiles OC[C@H]1O[C@@H](O[C@H]2C/C=C(\CO)/CCC3[C@@H](/C=C/2\C)OC(=O)C3=C)[C@@H]([C@H]([C@@H]1O)O)O
InChI InChI=1S/C21H30O9/c1-10-7-15-13(11(2)20(27)28-15)5-3-12(8-22)4-6-14(10)29-21-19(26)18(25)17(24)16(9-23)30-21/h4,7,13-19,21-26H,2-3,5-6,8-9H2,1H3/b10-7+,12-4-/t13?,14-,15+,16+,17+,18-,19+,21+/m0/s1
InChIKey LVLLXACEPRSSHZ-DKKHFUCHSA-N
Formula C21H30O9
HBA 9
HBD 5
MW 426.46
Rotatable Bonds 4
TPSA 145.91
LogP -0.68
Number Rings 3
Number Aromatic Rings 0
Heavy Atom Count 30
Formal Charge 0
Fraction CSP3 0.67
Exact Mass 426.19
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Launaea arborescens Asteraceae Plantae 43199

Showing of synonyms

  • Bitam F, Ciavatta ML, et al. (2008). Chemical characterisation of the terpenoid constituents of the Algerian plant Launaea arborescens. Phytochemistry,2008,69,2984-2992. [View] [PubMed]
Pubchem: 162922334

No compound-protein relationship available.

Structure

SMILES: C=C1C(=O)OC(C12)C=CC(CC=CCC2)OC3CCCCO3

Level: 1

Mol. Weight: 426.46 g/mol

Structure

SMILES: C=C1C(=O)OC(C12)C=CCCC=CCC2

Level: 0

Mol. Weight: 426.46 g/mol

Structure

SMILES: C1CCOCC1

Level: 0

Mol. Weight: 426.46 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-5.3
Human Oral Bioavailability 20%
Non-Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.950
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-1.37

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
0.750
Plasma Protein Binding
53.19
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
4.140
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-2.830
Biodegradation
Toxic
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.440
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
4.530
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
-27.870
Rat (Acute)
2.720
Rat (Chronic Oral)
3.130
Fathead Minnow
3.980
Respiratory Disease
Safe
Skin Sensitisation
Toxic
SR-ARE
Safe
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Toxic

General Properties

Boiling Point
498.640
Hydration Free Energy
-7.230
Log(D) at pH=7.4
0.590
Log(P)
-1.06
Log S
-1.53
Log(Vapor Pressure)
-13.25
Melting Point
151.86
pKa Acid
6.2
pKa Basic
5.74
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 0.8163
Serpin domain-containing protein H0ZQY2 H0ZQY2_TAEGU Taeniopygia guttata 3 0.8163
Laminarinase Q9WXN1 Q9WXN1_THEMA Thermotoga maritima 3 0.7812
Laminarinase Q9WXN1 Q9WXN1_THEMA Thermotoga maritima 3 0.7812
beta-glucosidase Q92AS9 Q92AS9_LISIN Listeria innocua serovar 6a 3 0.7738
beta-glucosidase Q92AS9 Q92AS9_LISIN Listeria innocua serovar 6a 3 0.7738
Putative b-glycan phosphorylase Q21MB1 Q21MB1_SACD2 Saccharophagus degradans 4 0.7183
Putative b-glycan phosphorylase Q21MB1 Q21MB1_SACD2 Saccharophagus degradans 4 0.7183

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