13-hydroxy-3-oxo-guaia-1alpha,5alphaH-7(11)-en-6beta,12-olide - Compound Card

13-hydroxy-3-oxo-guaia-1alpha,5alphaH-7(11)-en-6beta,12-olide

Select a section from the left sidebar

13-hydroxy-3-oxo-guaia-1alpha,5alphaH-7(11)-en-6beta,12-olide

Structure
Zoomed Structure
  • Family: Plantae - Asteraceae
  • Kingdom: Plantae
  • Class: Terpenoid
    • Subclass: Sesquiterpene Lactone
Canonical Smiles OCC1=C2CC[C@@H]([C@H]3[C@@]([C@@H]2OC1=O)(C)C(=O)CC3)C
InChI InChI=1S/C15H20O4/c1-8-3-4-9-10(7-16)14(18)19-13(9)15(2)11(8)5-6-12(15)17/h8,11,13,16H,3-7H2,1-2H3/t8-,11-,13+,15-/m0/s1
InChIKey SQBLZGPDZBFVEE-BUWBAVOPSA-N
Formula C15H20O4
HBA 4
HBD 1
MW 264.32
Rotatable Bonds 1
TPSA 63.6
LogP 1.62
Number Rings 3
Number Aromatic Rings 0
Heavy Atom Count 19
Formal Charge 0
Fraction CSP3 0.73
Exact Mass 264.14
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Ambrosia maritima Asteraceae Plantae 1028380

Showing of synonyms

  • Salam NAA, Mahmoud ZF, et al. (1984). Sesquiterpene lactones from Ambrosia maritima (Damssissa).. Phytochemistry,1984,23(12),2851-2853. [View]
Pubchem: 162968824
Nmrshiftdb2: 70048416

No compound-protein relationship available.

Structure

SMILES: C1C(=O)OC(C=12)C3C(CCC3=O)CCC2

Level: 0

Mol. Weight: 264.32 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.59
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.53
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.69

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.52
Plasma Protein Binding
41.09
Steady State Volume of Distribution
-

Metabolism

Breast Cancer Resistance Protein
Non-Inhibitor
CYP 1A2 Inhibitor
Non-Inhibitor
CYP 1A2 Substrate
Substrate
CYP 2C19 Inhibitor
Non-Inhibitor
CYP 2C19 Substrate
Non-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
8.78
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-0.4
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
-0.17
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
3.95
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
-0.53
Rat (Acute)
2.04
Rat (Chronic Oral)
1.76
Fathead Minnow
3.92
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
350.37
Hydration Free Energy
-7.58
Log(D) at pH=7.4
1.3
Log(P)
1.45
Log S
-2.52
Log(Vapor Pressure)
-6.12
Melting Point
158.83
pKa Acid
8.95
pKa Basic
5.77
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Liver carboxylesterase 1 P23141 EST1_HUMAN Homo sapiens 3 0.8793
Liver carboxylesterase 1 P23141 EST1_HUMAN Homo sapiens 3 0.8793
Succinate dehydrogenase [ubiquinone] flavoprotein subunit, mitochondrial Q0QF01 SDHA_PIG Sus scrofa 3 0.7762
Succinate dehydrogenase [ubiquinone] flavoprotein subunit, mitochondrial Q0QF01 SDHA_PIG Sus scrofa 3 0.7762
Genome polyprotein O92972 POLG_HCVJ4 Hepatitis C virus genotype 1b 2 0.7124
Genome polyprotein O92972 POLG_HCVJ4 Hepatitis C virus genotype 1b 2 0.7124

Download SDF