Moroccolide A - Compound Card

Moroccolide A

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Moroccolide A

Structure
Zoomed Structure
  • Family: Plantae - Asteraceae
  • Kingdom: Plantae
  • Class: Terpenoid
    • Subclass: Sesquiterpene Lactone
Canonical Smiles CC1=C2[C@H]3O[C@@]([C@@H]2[C@H]2[C@@H](CC1)C(=C)C(=O)O2)([C@H]3O)C
InChI InChI=1S/C15H18O4/c1-6-4-5-8-7(2)14(17)18-11(8)10-9(6)12-13(16)15(10,3)19-12/h8,10-13,16H,2,4-5H2,1,3H3/t8-,10-,11+,12+,13-,15-/m0/s1
InChIKey YTVDEYRARRBPLE-XNIAFVBGSA-N
Formula C15H18O4
HBA 4
HBD 1
MW 262.3
Rotatable Bonds 0
TPSA 55.76
LogP 1.34
Number Rings 5
Number Aromatic Rings 0
Heavy Atom Count 19
Formal Charge 0
Fraction CSP3 0.67
Exact Mass 262.12
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Warionia saharae Asteraceae Plantae 40727
2 Warionia saharae Asteraceae Plantae 40727

Showing of synonyms

  • Hilmi F, Gertsch J, et al. (2003). Cytotoxic versus anti-inflammatory effects in HeLa, Jurkat T and human peripheral blood cells caused by guaianolide-type sesquiterpene lactones. Bioorganic and Medicinal Chemistry,2003,11,3659-3663. [View] [PubMed]
  • Hilmi F, Sticher O, et al. (2002). New cytotoxic 6,7-cis and 6,7-trans configured guaianolides from Warionia saharae. Journal of Natural Products,2002,65,523-526. [View] [PubMed]
Pubchem: 44566947
Nmrshiftdb2: 70079922

No compound-protein relationship available.

Structure

SMILES: C1CCC(C(=C)C(=O)O2)C2C(C(O3)C4)C=1C34

Level: 0

Mol. Weight: 262.3 g/mol

Anti-inflammatory
Cytotoxic

Absorption

Caco-2 (logPapp)
-4.83
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.56
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.05

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.49
Plasma Protein Binding
38.96
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
Non-Inhibitor
CYP 2D6 Substrate
Non-Substrate
CYP 3A4 Inhibitor
Non-Inhibitor
CYP 3A4 Substrate
Substrate
OATP1B1
Non-Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
10.33
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-0.3
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
-1.59
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
4.29
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
1.5
Rat (Acute)
3.53
Rat (Chronic Oral)
1.74
Fathead Minnow
3.91
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
347.97
Hydration Free Energy
-7.86
Log(D) at pH=7.4
0.92
Log(P)
1.3
Log S
-2.36
Log(Vapor Pressure)
-6.97
Melting Point
157.79
pKa Acid
8.43
pKa Basic
5.39
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.8242
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.8242
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 3 0.7851
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 3 0.7851
Peptidyl-prolyl cis-trans isomerase FKBP1A P62942 FKB1A_HUMAN Homo sapiens 3 0.7753
Peptidyl-prolyl cis-trans isomerase FKBP1A P62942 FKB1A_HUMAN Homo sapiens 3 0.7753
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.7652
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.7652
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7384
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7384
Adenylate cyclase type 5 P30803 ADCY5_CANLF Canis lupus familiaris 3 0.7335
Adenylate cyclase type 5 P30803 ADCY5_CANLF Canis lupus familiaris 3 0.7335
Gastrotropin P51161 FABP6_HUMAN Homo sapiens 3 0.7252
Gastrotropin P51161 FABP6_HUMAN Homo sapiens 3 0.7252
Abscisic acid receptor PYL10 Q8H1R0 PYL10_ARATH Arabidopsis thaliana 3 0.7110
Abscisic acid receptor PYL10 Q8H1R0 PYL10_ARATH Arabidopsis thaliana 3 0.7110

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