3-acetoxy-5,7-dihydroxycarvotacetone - Compound Card

3-acetoxy-5,7-dihydroxycarvotacetone

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3-acetoxy-5,7-dihydroxycarvotacetone

Structure
Zoomed Structure
  • Family: Plantae - Asteraceae
  • Kingdom: Plantae
  • Class: Terpenoid
    • Subclass: Carvotacetone Derivative
Canonical Smiles OCC1=C[C@@H](OC(=O)C)C([C@@H](C1=O)O)C(C)C
InChI InChI=1S/C12H18O5/c1-6(2)10-9(17-7(3)14)4-8(5-13)11(15)12(10)16/h4,6,9-10,12-13,16H,5H2,1-3H3/t9-,10?,12+/m1/s1
InChIKey QEKUAMYPTPQAPS-MAZPRZIYSA-N
Formula C12H18O5
HBA 5
HBD 2
MW 242.27
Rotatable Bonds 3
TPSA 83.83
LogP 0.05
Number Rings 1
Number Aromatic Rings 0
Heavy Atom Count 17
Formal Charge 0
Fraction CSP3 0.67
Exact Mass 242.12
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: 242.27 g/mol

Anti-leishmanial
Anti-plasmodial
Anticancer

Absorption

Caco-2 (logPapp)
-4.82
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.32
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)
0.21
Plasma Protein Binding
28.43
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
5.93
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-0.53
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
Safe
hERG Blockers
Safe
Daphnia Maga
4.52
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
-1.18
Rat (Acute)
2.09
Rat (Chronic Oral)
2.34
Fathead Minnow
3.82
Respiratory Disease
Safe
Skin Sensitisation
Toxic
SR-ARE
Safe
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Safe

General Properties

Boiling Point
296.98
Hydration Free Energy
-12.72
Log(D) at pH=7.4
-0.1
Log(P)
0.19
Log S
-0.93
Log(Vapor Pressure)
-5.41
Melting Point
121.86
pKa Acid
7.1
pKa Basic
4.85
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Serpin domain-containing protein H0ZQY2 H0ZQY2_TAEGU Taeniopygia guttata 3 0.9430
Serpin domain-containing protein H0ZQY2 H0ZQY2_TAEGU Taeniopygia guttata 3 0.9430
Type IV / VI secretion system DotU domain-containing protein Q9KN50 Q9KN50_VIBCH Vibrio cholerae serotype O1 2 0.7669
Type IV / VI secretion system DotU domain-containing protein Q9KN50 Q9KN50_VIBCH Vibrio cholerae serotype O1 2 0.7669
Macrophage metalloelastase P39900 MMP12_HUMAN Homo sapiens 3 0.7360
Macrophage metalloelastase P39900 MMP12_HUMAN Homo sapiens 3 0.7360
Phospholipase A2, major isoenzyme P00592 PA21B_PIG Sus scrofa 3 0.7068
Phospholipase A2, major isoenzyme P00592 PA21B_PIG Sus scrofa 3 0.7068
ADP-ribosylation factor 1 P84080 ARF1_BOVIN Bos taurus 3 0.7057
ADP-ribosylation factor 1 P84080 ARF1_BOVIN Bos taurus 3 0.7057

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