Kandavanolide - Compound Card

Kandavanolide

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Kandavanolide

Structure
Zoomed Structure
  • Family: Plantae - Asteraceae
  • Kingdom: Plantae
  • Class: Terpenoid
    • Subclass: Sesquiterpene Lactone
Canonical Smiles CC(=O)O[C@H]1C[C@@H]2[C@H](C1=C)[C@H]1OC(=O)C(=C)[C@@H]1[C@H](CC2=C)O
InChI InChI=1S/C17H20O5/c1-7-5-12(19)15-9(3)17(20)22-16(15)14-8(2)13(6-11(7)14)21-10(4)18/h11-16,19H,1-3,5-6H2,4H3/t11-,12-,13-,14-,15+,16+/m0/s1
InChIKey ZOQZWYXGJUDJFV-OSLXHZNNSA-N
Formula C17H20O5
HBA 5
HBD 1
MW 304.34
Rotatable Bonds 1
TPSA 72.83
LogP 1.53
Number Rings 3
Number Aromatic Rings 0
Heavy Atom Count 22
Formal Charge 0
Fraction CSP3 0.53
Exact Mass 304.13
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Centaurea acaulis Asteraceae Plantae 2969722

Showing of synonyms

  • Bentamène A, Benayache S, et al. (2005). A new guaianolide and other sesquiterpene lactones from Centaurea acaulis L. (Asteraceae). Biochemical Systematics and Ecology,2005,33,1061-1065. [View]
Pubchem: 101036702
Nmrshiftdb2: 70019460

No compound-protein relationship available.

Structure

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

Level: 0

Mol. Weight: 304.34 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.63
Human Oral Bioavailability 20%
Non-Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.61
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.44

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.51
Plasma Protein Binding
52.31
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
10.65
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-0.21
Biodegradation
Safe
Carcinogenesis
Toxic
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
-0.58
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
4.47
Micronucleos
Safe
NR-AhR
Safe
NR-AR
Safe
NR-AR-LBD
Safe
NR-Aromatase
Safe
NR-ER
Safe
NR-ER-LBD
Safe
NR-GR
Toxic
NR-PPAR-gamma
Safe
NR-TR
Safe
T. Pyriformis
-0.27
Rat (Acute)
3.44
Rat (Chronic Oral)
1.88
Fathead Minnow
3.92
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
351.01
Hydration Free Energy
-6.96
Log(D) at pH=7.4
0.95
Log(P)
1.64
Log S
-2.83
Log(Vapor Pressure)
-6.89
Melting Point
162.38
pKa Acid
7.32
pKa Basic
4.72
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 3 0.9226
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 3 0.9226
Liver carboxylesterase 1 P23141 EST1_HUMAN Homo sapiens 3 0.9168
Liver carboxylesterase 1 P23141 EST1_HUMAN Homo sapiens 3 0.9168
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 3 0.8622
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 3 0.8622
N-alpha-acetyltransferase 50 Q9GZZ1 NAA50_HUMAN Homo sapiens 3 0.7643
N-alpha-acetyltransferase 50 Q9GZZ1 NAA50_HUMAN Homo sapiens 3 0.7643
Reaction center protein L chain P0C0Y7 RCEH_RHOSH Rhodobacter sphaeroides 3 0.7403
Reaction center protein L chain P0C0Y7 RCEH_RHOSH Rhodobacter sphaeroides 3 0.7403

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