2alpha-hydroxyalantolactone - Compound Card

2alpha-hydroxyalantolactone

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2alpha-hydroxyalantolactone

Structure
Zoomed Structure
  • Family: Plantae - Asteraceae
  • Kingdom: Plantae
  • Class: Terpenoid
    • Subclass: Sesquiterpene Lactone
Canonical Smiles OC1CC(C)C2=CC3C(CC2(C1)C)OC(=O)C3=C
InChI InChI=1S/C15H20O3/c1-8-4-10(16)6-15(3)7-13-11(5-12(8)15)9(2)14(17)18-13/h5,8,10-11,13,16H,2,4,6-7H2,1,3H3
InChIKey FZSKLHDEGWSLTB-UHFFFAOYSA-N
Formula C15H20O3
HBA 3
HBD 1
MW 248.32
Rotatable Bonds 0
TPSA 46.53
LogP 2.21
Number Rings 3
Number Aromatic Rings 0
Heavy Atom Count 18
Formal Charge 0
Fraction CSP3 0.67
Exact Mass 248.14
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Pulicaria undulata Asteraceae 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: 4039117
Nmrshiftdb2: 70066803
CPRiL: 412711
Structure

SMILES: C=C1C(=O)OC(C12)CC3C(=C2)CCCC3

Level: 0

Mol. Weight: 248.32 g/mol

Anti-inflammatory

Absorption

Caco-2 (logPapp)
-4.86
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.380
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.5

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
0.610
Plasma Protein Binding
29.7
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
Substrate
CYP 3A4 Inhibitor
Non-Inhibitor
CYP 3A4 Substrate
Non-Substrate
OATP1B1
Non-Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
11.180
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
0.670
Biodegradation
Safe
Carcinogenesis
Toxic
Crustacean
Toxic
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
-0.800
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
3.840
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
3.980
Rat (Acute)
2.330
Rat (Chronic Oral)
1.810
Fathead Minnow
4.070
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
316.280
Hydration Free Energy
-6.350
Log(D) at pH=7.4
1.760
Log(P)
1.88
Log S
-2.75
Log(Vapor Pressure)
-4.46
Melting Point
96.63
pKa Acid
9.3
pKa Basic
6.41
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 0.8217
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 3 0.8217
Epoxide hydrolase Q41415 Q41415_SOLTU Solanum tuberosum 3 0.7339
Epoxide hydrolase Q41415 Q41415_SOLTU Solanum tuberosum 3 0.7339
Abscisic acid receptor PYL3 Q9SSM7 PYL3_ARATH Arabidopsis thaliana 2 0.7208
Abscisic acid receptor PYL3 Q9SSM7 PYL3_ARATH Arabidopsis thaliana 2 0.7208
Abscisic acid receptor PYL2 O80992 PYL2_ARATH Arabidopsis thaliana 2 0.7134
Abscisic acid receptor PYL2 O80992 PYL2_ARATH Arabidopsis thaliana 2 0.7134
Sulfotransferase 2A1 Q06520 ST2A1_HUMAN Homo sapiens 2 0.7101
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7101
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7101
Sulfotransferase 2A1 Q06520 ST2A1_HUMAN Homo sapiens 2 0.7101
Cytochrome P450 monooxygenase Q5YNS8 Q5YNS8_NOCFA Nocardia farcinica 2 0.7085
Cytochrome P450 monooxygenase Q5YNS8 Q5YNS8_NOCFA Nocardia farcinica 2 0.7085
Sulfotransferase 2B1 O00204 ST2B1_HUMAN Homo sapiens 2 0.7068
Sulfotransferase 2B1 O00204 ST2B1_HUMAN Homo sapiens 2 0.7068
Abscisic acid receptor PYR1 O49686 PYR1_ARATH Arabidopsis thaliana 3 0.7038
Abscisic acid receptor PYR1 O49686 PYR1_ARATH Arabidopsis thaliana 3 0.7038
Abscisic acid receptor PYL9 Q84MC7 PYL9_ARATH Arabidopsis thaliana 3 0.7002
Abscisic acid receptor PYL9 Q84MC7 PYL9_ARATH Arabidopsis thaliana 3 0.7002

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