3alpha-chloro-4beta,10beta-dihydroxy-1beta,2beta-epoxy-5alpha,7alphaH-guaia-11(13)-en-12,6alpha-olide - Compound Card

3alpha-chloro-4beta,10beta-dihydroxy-1beta,2beta-epoxy-5alpha,7alphaH-guaia-11(13)-en-12,6alpha-olide

Select a section from the left sidebar

3alpha-chloro-4beta,10beta-dihydroxy-1beta,2beta-epoxy-5alpha,7alphaH-guaia-11(13)-en-12,6alpha-olide

Structure
Zoomed Structure
  • Family: Plantae - Asteraceae
  • Kingdom: Plantae
  • Class: Terpenoid
    • Subclass: Sesquiterpene Lactone
Canonical Smiles O[C@H]1C[C@@H]2[C@H]([C@@H]1C)[C@H]1OC(=O)[C@H]([C@@H]1C[C@@H](C2=C)O)C
InChI InChI=1S/C15H22O4/c1-6-9-4-12(17)8(3)13(9)14-10(5-11(6)16)7(2)15(18)19-14/h7-14,16-17H,1,4-5H2,2-3H3/t7-,8+,9-,10-,11-,12-,13-,14-/m0/s1
InChIKey FZHVZHPJLXWJIZ-DZKMKBNLSA-N
Formula C15H22O4
HBA 4
HBD 2
MW 266.34
Rotatable Bonds 0
TPSA 66.76
LogP 1.12
Number Rings 3
Number Aromatic Rings 0
Heavy Atom Count 19
Formal Charge 0
Fraction CSP3 0.8
Exact Mass 266.15
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Arctotis grandis Asteraceae Plantae 41478
2 Achillea ligustica Asteraceae Plantae 282745
3 Senecio burtoni Asteraceae Plantae 18794

Showing of synonyms

  • Mahmoud AA, Al-Shihry SS, et al. (2012). A new epimeric sesquiterpene lactone from Achillea ligustica.. Records of Natural Products,2012,6(1),21-27. [View]
  • Halim AF, Zaghloul AM, et al. (1983). Further guaianolides from Arctotis grandis.. Phytochemistry,1983,22(6),1510-1512.. [View]
  • Ndom JC (2023). Ultra-short pulses compression and supercontinuum generation in optical waveguides : cases of SMFs, SOI-waveguides and CS 2 -LCPCFs. PhD Thesis 2023, Faculty of Science, University of Yaounde I, Cameroon. [View]
Pubchem: 163078531

No compound-protein relationship available.

Structure

SMILES: C1CCC2C(=C)CCC(C3C12)CC(=O)O3

Level: 0

Mol. Weight: 266.34 g/mol

Antibacterial
Antifungal

Absorption

Caco-2 (logPapp)
-4.71
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.4
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.35

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.42
Plasma Protein Binding
50.2
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
Non-Substrate
CYP 3A4 Inhibitor
Non-Inhibitor
CYP 3A4 Substrate
Non-Substrate
OATP1B1
Non-Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
9.7
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-0.62
Biodegradation
Safe
Carcinogenesis
Toxic
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
-0.95
Liver Injury II
Safe
hERG Blockers
Safe
Daphnia Maga
3.93
Micronucleos
Safe
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
-0.92
Rat (Acute)
3.84
Rat (Chronic Oral)
1.93
Fathead Minnow
3.88
Respiratory Disease
Safe
Skin Sensitisation
Safe
SR-ARE
Safe
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Safe

General Properties

Boiling Point
359.04
Hydration Free Energy
-8.58
Log(D) at pH=7.4
0.32
Log(P)
0.87
Log S
-1.69
Log(Vapor Pressure)
-6.6
Melting Point
173.3
pKa Acid
8.25
pKa Basic
5.77
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Nuclear receptor subfamily 1 group I member 3 O35627 NR1I3_MOUSE Mus musculus 3 0.8987
Nuclear receptor subfamily 1 group I member 3 O35627 NR1I3_MOUSE Mus musculus 3 0.8987
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.8911
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.8911
Gastrotropin P51161 FABP6_HUMAN Homo sapiens 3 0.8085
Gastrotropin P51161 FABP6_HUMAN Homo sapiens 3 0.8085
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.8021
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.8021
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.8019
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.8019
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.7924
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.7924
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7878
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7878
Fatty acid-binding protein, liver P80226 FABPL_CHICK Gallus gallus 3 0.7869
Fatty acid-binding protein, liver P80226 FABPL_CHICK Gallus gallus 3 0.7869
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7865
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7865
Progesterone receptor P06401 PRGR_HUMAN Homo sapiens 3 0.7346
Progesterone receptor P06401 PRGR_HUMAN Homo sapiens 3 0.7346
Cytochrome P450 Q93H81 Q93H81_STRAX Streptomyces avermitilis 3 0.7328
Cytochrome P450 Q93H81 Q93H81_STRAX Streptomyces avermitilis 3 0.7328
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 2 0.7285
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 2 0.7285
Succinate dehydrogenase [ubiquinone] flavoprotein subunit, mitochondrial Q0QF01 SDHA_PIG Sus scrofa 3 0.7113
Succinate dehydrogenase [ubiquinone] flavoprotein subunit, mitochondrial Q0QF01 SDHA_PIG Sus scrofa 3 0.7113
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.7077
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.7077
Mineralocorticoid receptor P08235 MCR_HUMAN Homo sapiens 3 0.7069
Mineralocorticoid receptor P08235 MCR_HUMAN Homo sapiens 3 0.7069

Download SDF