Malacitanolide - Compound Card

Malacitanolide

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Malacitanolide

Structure
Zoomed Structure
  • Family: Plantae - Asteraceae
  • Kingdom: Plantae
  • Class: Terpenoid
    • Subclass: Sesquiterpene
Canonical Smiles OC[C@@H](C(=C)C(=O)O[C@H]1C[C@@]2(C)[C@H](O)CC[C@@H]([C@@H]2[C@@H]2[C@@H]1C(=C)C(=O)O2)C=O)O
InChI InChI=1S/C20H26O8/c1-9(12(23)8-22)18(25)27-13-6-20(3)14(24)5-4-11(7-21)16(20)17-15(13)10(2)19(26)28-17/h7,11-17,22-24H,1-2,4-6,8H2,3H3/t11-,12+,13+,14-,15-,16-,17+,20+/m1/s1
InChIKey OZJAAHIGUMFSHY-MYBIUHGVSA-N
Formula C20H26O8
HBA 8
HBD 3
MW 394.42
Rotatable Bonds 5
TPSA 130.36
LogP -0.1
Number Rings 3
Number Aromatic Rings 0
Heavy Atom Count 28
Formal Charge 0
Fraction CSP3 0.65
Exact Mass 394.16
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Centaurea papposa Asteraceae Plantae 1006337

Showing of synonyms

  • Grafakou M.E, Barda C, et al. (2022). In vitro cytotoxic and anti-inflammatory activities of sesquiterpene lactones from Centaurea papposa (Coss.) Greuter. Natural product research, 2022, 36(12), 3211-3215. [View] [PubMed]
Pubchem: 10739390
Nmrshiftdb2: 60070340

No compound-protein relationship available.

Structure

SMILES: C=C1C(=O)OC(C12)C3C(CC2)CCCC3

Level: 0

Mol. Weight: 394.42 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.92
Human Oral Bioavailability 20%
Non-Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.78
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Substrate
Skin Permeability
-2.2

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
0.48
Plasma Protein Binding
48.14
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
6.27
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-2.04
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.34
Liver Injury II
Safe
hERG Blockers
Safe
Daphnia Maga
5.08
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
-9.93
Rat (Acute)
4.93
Rat (Chronic Oral)
2.0
Fathead Minnow
4.01
Respiratory Disease
Safe
Skin Sensitisation
Safe
SR-ARE
Safe
SR-ATAD5
Toxic
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Toxic

General Properties

Boiling Point
430.39
Hydration Free Energy
-9.61
Log(D) at pH=7.4
0.8
Log(P)
-0.66
Log S
-2.22
Log(Vapor Pressure)
-9.69
Melting Point
162.5
pKa Acid
5.58
pKa Basic
4.99
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Vitamin D-binding protein P02774 VTDB_HUMAN Homo sapiens 2 0.7286

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