Crepidiaside A - Compound Card

Crepidiaside A

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Crepidiaside A

Structure
Zoomed Structure
  • Family: Plantae - Asteraceae
  • Kingdom: Plantae
  • Class: Terpenoid
    • Subclass: Sesquiterpene Lactone
Canonical Smiles OC[C@H]1O[C@@H](OCC2=CC(=O)C3=C(C)CC[C@@H]4[C@@H]([C@@H]23)OC(=O)C4=C)[C@@H]([C@H]([C@@H]1O)O)O
InChI InChI=1S/C21H26O9/c1-8-3-4-11-9(2)20(27)30-19(11)15-10(5-12(23)14(8)15)7-28-21-18(26)17(25)16(24)13(6-22)29-21/h5,11,13,15-19,21-22,24-26H,2-4,6-7H2,1H3/t11-,13+,15-,16+,17-,18+,19-,21+/m0/s1
InChIKey GHSRDMYBBWWNGL-NPPWKTABSA-N
Formula C21H26O9
HBA 9
HBD 4
MW 422.43
Rotatable Bonds 4
TPSA 142.75
LogP -0.86
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 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: 13855728
Nmrshiftdb2: 20171644

No compound-protein relationship available.

Structure

SMILES: C1CCC(C(=C)C(=O)O2)C2C(C=13)C(=CC3=O)COC4CCCCO4

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)
-5.27
Human Oral Bioavailability 20%
Non-Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.870
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Substrate
Skin Permeability
-1.61

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
0.810
Plasma Protein Binding
63.67
Steady State Volume of Distribution
-

Metabolism

Breast Cancer Resistance Protein
Non-Inhibitor
CYP 1A2 Inhibitor
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
4.930
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-3.020
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.460
Liver Injury II
Safe
hERG Blockers
Safe
Daphnia Maga
4.990
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
-35.340
Rat (Acute)
3.320
Rat (Chronic Oral)
3.340
Fathead Minnow
3.980
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
495.700
Hydration Free Energy
-6.140
Log(D) at pH=7.4
0.810
Log(P)
-1.04
Log S
-1.91
Log(Vapor Pressure)
-13.01
Melting Point
194.91
pKa Acid
5.43
pKa Basic
5.16
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
beta-glucosidase Q92AS9 Q92AS9_LISIN Listeria innocua serovar 6a 3 0.7813
beta-glucosidase Q92AS9 Q92AS9_LISIN Listeria innocua serovar 6a 3 0.7813
Serpin domain-containing protein H0ZQY2 H0ZQY2_TAEGU Taeniopygia guttata 3 0.7709
Serpin domain-containing protein H0ZQY2 H0ZQY2_TAEGU Taeniopygia guttata 3 0.7709
Sex hormone-binding globulin P04278 SHBG_HUMAN Homo sapiens 2 0.7240
Sex hormone-binding globulin P04278 SHBG_HUMAN Homo sapiens 2 0.7240

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