5alpha-hydroperoxyivalin - Compound Card

5alpha-hydroperoxyivalin

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5alpha-hydroperoxyivalin

Structure
Zoomed Structure
  • Family: Asteraceae-Compositae
  • Kingdom: Plantae
  • Class: Terpenoid
    • Subclass: Sesquiterpene Lactone
Canonical Smiles OO[C@]12C[C@H]3[C@@H](C[C@@]2(C)C[C@H](CC1=C)O)OC(=O)C3=C
InChI InChI=1S/C15H20O5/c1-8-4-10(16)5-14(3)7-12-11(6-15(8,14)20-18)9(2)13(17)19-12/h10-12,16,18H,1-2,4-7H2,3H3/t10-,11+,12+,14+,15+/m0/s1
InChIKey JWOOWPXMOCPZQR-PGKPSXLWSA-N
Formula C15H20O5
HBA 5
HBD 2
MW 280.32
Rotatable Bonds 1
TPSA 75.99
LogP 1.82
Number Rings 3
Number Aromatic Rings 0
Heavy Atom Count 20
Formal Charge 0
Fraction CSP3 0.67
Exact Mass 280.13
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Pulicaria undulata Asteraceae-Compositae Plantae 119186

Showing of synonyms

  • Hegazy MEF, Matsuda H, et al. (2012). Sesquiterpenes from an Egyptian herbal medicine, Pulicaria undulate, with inhibitory effects on nitric oxide production in RAW264.7 macrophage cells. Chemical and Pharmaceutical Bulletin,2012,60(3),363-370. [View] [PubMed]
Pubchem: 56969012
Nmrshiftdb2: 70093929

No compound-protein relationship available.

Structure

SMILES: C=C1C(=O)OC(C12)CC3C(C2)C(=C)CCC3

Level: 0

Mol. Weight: 218.3 g/mol

Anti-inflammatory

Absorption

Caco-2 (logPapp)
-4.65
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.480
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.46

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.410
Plasma Protein Binding
48.84
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
Substrate
CYP 2C9 Inhibitor
Non-Inhibitor
CYP 2C9 Substrate
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
10.220
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-0.330
Biodegradation
Safe
Carcinogenesis
Toxic
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
-0.740
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
4.050
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
-0.010
Rat (Acute)
3.590
Rat (Chronic Oral)
1.750
Fathead Minnow
3.920
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
335.180
Hydration Free Energy
-10.980
Log(D) at pH=7.4
0.650
Log(P)
0.37
Log S
-2.19
Log(Vapor Pressure)
-6.35
Melting Point
156.79
pKa Acid
7.66
pKa Basic
5.08
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 3 0.8701
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 3 0.8701
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.8670
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.8670
Corticosteroid-binding globulin P08185 CBG_HUMAN Homo sapiens 3 0.7863
Corticosteroid-binding globulin P08185 CBG_HUMAN Homo sapiens 3 0.7863
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 3 0.7820
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 3 0.7820
Sulfotransferase 2A1 Q06520 ST2A1_HUMAN Homo sapiens 3 0.7772
Sulfotransferase 2A1 Q06520 ST2A1_HUMAN Homo sapiens 3 0.7772
Sulfotransferase 2B1 O00204 ST2B1_HUMAN Homo sapiens 2 0.7514
Sulfotransferase 2B1 O00204 ST2B1_HUMAN Homo sapiens 2 0.7514
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 3 0.7452
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 3 0.7452
Xylose isomerase P24300 XYLA_STRRU Streptomyces rubiginosus 3 0.7436
Xylose isomerase P24300 XYLA_STRRU Streptomyces rubiginosus 3 0.7436
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7333
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7333
Aromatase P11511 CP19A_HUMAN Homo sapiens 3 0.7294
Aromatase P11511 CP19A_HUMAN Homo sapiens 3 0.7294
Cytochrome P450 monooxygenase Q5YNS8 Q5YNS8_NOCFA Nocardia farcinica 3 0.7289
Cytochrome P450 monooxygenase Q5YNS8 Q5YNS8_NOCFA Nocardia farcinica 3 0.7289
Sulfotransferase 2A1 Q06520 ST2A1_HUMAN Homo sapiens 3 0.7120
Sulfotransferase 2A1 Q06520 ST2A1_HUMAN Homo sapiens 3 0.7120
Cytochrome P450 monooxygenase Q5YNS8 Q5YNS8_NOCFA Nocardia farcinica 2 0.7104
Cytochrome P450 monooxygenase Q5YNS8 Q5YNS8_NOCFA Nocardia farcinica 2 0.7104

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