3,7-dihydroxy-5-tigloyloxycarvotacetone - Compound Card

3,7-dihydroxy-5-tigloyloxycarvotacetone

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3,7-dihydroxy-5-tigloyloxycarvotacetone

Structure
Zoomed Structure
  • Family: Plantae - Asteraceae
  • Kingdom: Plantae
  • Class: Terpenoid
    • Subclass: Carvotacetone Derivative
Canonical Smiles C/C=C(/C(=O)O[C@H]1C(C(C)C)[C@H](O)C=C(C1=O)CO)\C
InChI InChI=1S/C15H22O5/c1-5-9(4)15(19)20-14-12(8(2)3)11(17)6-10(7-16)13(14)18/h5-6,8,11-12,14,16-17H,7H2,1-4H3/b9-5+/t11-,12?,14+/m1/s1
InChIKey DQAVAZNOXSQZNF-QANHFJFBSA-N
Formula C15H22O5
HBA 5
HBD 2
MW 282.34
Rotatable Bonds 4
TPSA 83.83
LogP 1.0
Number Rings 1
Number Aromatic Rings 0
Heavy Atom Count 20
Formal Charge 0
Fraction CSP3 0.6
Exact Mass 282.15
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Sphaeranthus bullatus Asteraceae Plantae 1548657

Showing of synonyms

  • Machumi F, Yenesew A, et al. (2012). Antiparasitic and anticancer carvotacetone derivatives of Sphaeranthus bullatus. Natural Product Communications,2012,7(9),1123-1126. [View] [PubMed]

No compound-protein relationship available.

Structure

SMILES: O=C1C=CCCC1

Level: 0

Mol. Weight: 282.34 g/mol

Anti-leishmanial
Anti-plasmodial
Anticancer

Absorption

Caco-2 (logPapp)
-4.68
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.41
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.97

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
0.27
Plasma Protein Binding
43.05
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
Non-Substrate
OATP1B1
Non-Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
5.28
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-0.46
Biodegradation
Safe
Carcinogenesis
Toxic
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.7
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
4.96
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
-0.51
Rat (Acute)
2.2
Rat (Chronic Oral)
2.34
Fathead Minnow
4.04
Respiratory Disease
Safe
Skin Sensitisation
Safe
SR-ARE
Safe
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Safe

General Properties

Boiling Point
316.34
Hydration Free Energy
-11.67
Log(D) at pH=7.4
1.17
Log(P)
1.66
Log S
-1.77
Log(Vapor Pressure)
-5.6
Melting Point
118.52
pKa Acid
6.34
pKa Basic
4.77
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.8891
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.8891
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.8057
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.8057
Aldo-keto reductase family 1 member C3 P42330 AK1C3_HUMAN Homo sapiens 3 0.7926
Aldo-keto reductase family 1 member C3 P42330 AK1C3_HUMAN Homo sapiens 3 0.7926
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 3 0.7685
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 3 0.7685
Fatty acid-binding protein, liver P80226 FABPL_CHICK Gallus gallus 3 0.7623
Fatty acid-binding protein, liver P80226 FABPL_CHICK Gallus gallus 3 0.7623
Gastrotropin P51161 FABP6_HUMAN Homo sapiens 3 0.7586
Gastrotropin P51161 FABP6_HUMAN Homo sapiens 3 0.7586
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7535
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7535
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 2 0.7192
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 2 0.7192
Cytochrome P450 Q93H81 Q93H81_STRAX Streptomyces avermitilis 3 0.7097
Cytochrome P450 Q93H81 Q93H81_STRAX Streptomyces avermitilis 3 0.7097
Aldo-keto reductase family 1 member C1 Q04828 AK1C1_HUMAN Homo sapiens 2 0.7089
Aldo-keto reductase family 1 member C1 Q04828 AK1C1_HUMAN Homo sapiens 2 0.7089

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