Macrocliniside A - Compound Card

Macrocliniside A

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Macrocliniside A

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@@H]3[C@H](C2=C)[C@H]2OC(=O)C(=C)[C@@H]2C[C@H](C3=C)O)[C@@H]([C@H]([C@@H]1O)O)O
InChI InChI=1S/C21H28O9/c1-7-10-5-13(28-21-18(26)17(25)16(24)14(6-22)29-21)9(3)15(10)19-11(4-12(7)23)8(2)20(27)30-19/h10-19,21-26H,1-6H2/t10-,11-,12+,13-,14+,15-,16+,17-,18+,19-,21+/m0/s1
InChIKey ARJUJAMZTUUZNZ-NJQUUYHGSA-N
Formula C21H28O9
HBA 9
HBD 5
MW 424.45
Rotatable Bonds 3
TPSA 145.91
LogP -1.22
Number Rings 4
Number Aromatic Rings 0
Heavy Atom Count 30
Formal Charge 0
Fraction CSP3 0.67
Exact Mass 424.17
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: 10455028
Nmrshiftdb2: 60066484

No compound-protein relationship available.

Structure

SMILES: O=C(O1)C(=C)C(C1C23)CCC(=C)C3CC(C2=C)OC4CCCCO4

Level: 1

Mol. Weight: 424.45 g/mol

Structure

SMILES: O=C(O1)C(=C)C(C1C23)CCC(=C)C3CCC2=C

Level: 0

Mol. Weight: 424.45 g/mol

Structure

SMILES: C1CCOCC1

Level: 0

Mol. Weight: 424.45 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-5.49
Human Oral Bioavailability 20%
Non-Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.930
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Substrate
Skin Permeability
-1.4

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
0.800
Plasma Protein Binding
64.73
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
3.160
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-2.950
Biodegradation
Toxic
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
-0.060
Liver Injury II
Safe
hERG Blockers
Safe
Daphnia Maga
4.230
Micronucleos
Toxic
NR-AhR
Safe
NR-AR
Safe
NR-AR-LBD
Toxic
NR-Aromatase
Safe
NR-ER
Safe
NR-ER-LBD
Safe
NR-GR
Safe
NR-PPAR-gamma
Safe
NR-TR
Safe
T. Pyriformis
-34.380
Rat (Acute)
3.940
Rat (Chronic Oral)
3.110
Fathead Minnow
3.890
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
496.580
Hydration Free Energy
-6.880
Log(D) at pH=7.4
0.590
Log(P)
-1.14
Log S
-1.62
Log(Vapor Pressure)
-13.84
Melting Point
167.16
pKa Acid
5.74
pKa Basic
5.22
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Laminarinase Q9WXN1 Q9WXN1_THEMA Thermotoga maritima 3 0.8140
Laminarinase Q9WXN1 Q9WXN1_THEMA Thermotoga maritima 3 0.8140
beta-glucosidase Q92AS9 Q92AS9_LISIN Listeria innocua serovar 6a 3 0.7824
beta-glucosidase Q92AS9 Q92AS9_LISIN Listeria innocua serovar 6a 3 0.7824
Putative b-glycan phosphorylase Q21MB1 Q21MB1_SACD2 Saccharophagus degradans 4 0.7305
Putative b-glycan phosphorylase Q21MB1 Q21MB1_SACD2 Saccharophagus degradans 4 0.7305
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 2 0.7086
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 2 0.7086

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