9alpha-hydroxyparthenolide - Compound Card

9alpha-hydroxyparthenolide

Select a section from the left sidebar

9alpha-hydroxyparthenolide

Structure
Zoomed Structure
  • Family: Plantae - Asteraceae
  • Kingdom: Plantae
  • Class: Terpenoid
    • Subclass: Sesquiterpene Lactone
Canonical Smiles C/C/1=C\CC[C@@]2(C)O[C@H]2[C@@H]2[C@@H](C[C@H]1O)C(=C)C(=O)O2
InChI InChI=1S/C15H20O4/c1-8-5-4-6-15(3)13(19-15)12-10(7-11(8)16)9(2)14(17)18-12/h5,10-13,16H,2,4,6-7H2,1,3H3/b8-5+/t10-,11+,12-,13-,15+/m0/s1
InChIKey RZUCCKARTVHQBW-ZFDNOKKTSA-N
Formula C15H20O4
HBA 4
HBD 1
MW 264.32
Rotatable Bonds 0
TPSA 59.06
LogP 1.73
Number Rings 3
Number Aromatic Rings 0
Heavy Atom Count 19
Formal Charge 0
Fraction CSP3 0.67
Exact Mass 264.14
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Anvillea radiata Asteraceae Plantae 159630

Showing of synonyms

  • El Hassany B, El Hanbali F, et al. (2004). Germacranolides from Anvillea radiata.. Fitoterapia,2004,75,573- 576. [View] [PubMed]
Pubchem: 14466187
Nmrshiftdb2: 70107730

No compound-protein relationship available.

Structure

SMILES: C=C1C(=O)OC2C1CCC=CCCC(O3)C23

Level: 0

Mol. Weight: 264.32 g/mol

Antibacterial
Cytotoxic

Absorption

Caco-2 (logPapp)
-5.17
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.42
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.76

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.19
Plasma Protein Binding
19.06
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
15.68
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Toxic
Bioconcentration Factor
0.49
Biodegradation
Toxic
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Toxic
Maximum Tolerated Dose
-0.79
Liver Injury II
Safe
hERG Blockers
Safe
Daphnia Maga
3.92
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
0.02
Rat (Acute)
3.1
Rat (Chronic Oral)
1.73
Fathead Minnow
3.92
Respiratory Disease
Toxic
Skin Sensitisation
Toxic
SR-ARE
Safe
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Toxic

General Properties

Boiling Point
352.63
Hydration Free Energy
-7.18
Log(D) at pH=7.4
0.72
Log(P)
1.53
Log S
-2.22
Log(Vapor Pressure)
-5.54
Melting Point
84.2
pKa Acid
6.29
pKa Basic
4.16
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 0.7691
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.7691
Serpin domain-containing protein H0ZQY2 H0ZQY2_TAEGU Taeniopygia guttata 3 0.7659
Serpin domain-containing protein H0ZQY2 H0ZQY2_TAEGU Taeniopygia guttata 3 0.7659
Fatty acid-binding protein, liver P80226 FABPL_CHICK Gallus gallus 2 0.7455
Fatty acid-binding protein, liver P80226 FABPL_CHICK Gallus gallus 2 0.7455
Probable NDP-rhamnosyltransferase Q9ALM8 Q9ALM8_SACSN Saccharopolyspora spinosa 2 0.7421
Probable NDP-rhamnosyltransferase Q9ALM8 Q9ALM8_SACSN Saccharopolyspora spinosa 2 0.7421
Xylose isomerase P24300 XYLA_STRRU Streptomyces rubiginosus 3 0.7280
Xylose isomerase P24300 XYLA_STRRU Streptomyces rubiginosus 3 0.7280
Trichothecene 15-O-acetyltransferase TRI3 Q9C1B7 TRI3_FUSSP Fusarium sporotrichioides 3 0.7279
Trichothecene 15-O-acetyltransferase TRI3 Q9C1B7 TRI3_FUSSP Fusarium sporotrichioides 3 0.7279
Nuclear receptor ROR-gamma P51449 RORG_HUMAN Homo sapiens 2 0.7210
Nuclear receptor ROR-gamma P51449 RORG_HUMAN Homo sapiens 2 0.7210
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 2 0.7092
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 2 0.7092
Peptidyl-prolyl cis-trans isomerase FKBP1A P62942 FKB1A_HUMAN Homo sapiens 3 0.7091
Peptidyl-prolyl cis-trans isomerase FKBP1A P62942 FKB1A_HUMAN Homo sapiens 3 0.7091
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7075
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7075

Download SDF