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

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

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4alpha,10alpha-dihydroxy-1alpha,2alpha-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 CC(=O)O[C@H]1C[C@@](C)(O)[C@]23[C@@H]([C@@H]4[C@H]1[C@H](C)C(=O)O4)[C@]([C@@H]([C@@H]3O2)Cl)(C)O
InChI InChI=1S/C17H23ClO7/c1-6-9-8(23-7(2)19)5-15(3,21)17-11(10(9)24-14(6)20)16(4,22)12(18)13(17)25-17/h6,8-13,21-22H,5H2,1-4H3/t6-,8-,9-,10-,11-,12+,13-,15+,16-,17+/m0/s1
InChIKey CGAKJWNQAYBPPE-GFGMUQLFSA-N
Formula C17H23ClO7
HBA 7
HBD 2
MW 374.82
Rotatable Bonds 1
TPSA 105.59
LogP 0.38
Number Rings 4
Number Aromatic Rings 0
Heavy Atom Count 25
Formal Charge 0
Fraction CSP3 0.88
Exact Mass 374.11
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Achillea ligustica Asteraceae Plantae 282745

Showing of synonyms

  • Hegazy MEF, Mohamed AEHH, et al. (2014). A new chlorine-containing sesquiterpene lactone from Achillea ligustica.. Zeitschrift für Naturforschung B,2014,63(1),105-107. [View]
Pubchem: 162855724
Nmrshiftdb2: 60055084

No compound-protein relationship available.

Structure

SMILES: C123C(O3)CCC1C4C(CC(=O)O4)CCC2

Level: 0

Mol. Weight: 374.82 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-5.28
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.76
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.54

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.16
Plasma Protein Binding
24.36
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
Inhibitor
CYP 3A4 Substrate
Substrate
OATP1B1
Non-Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
10.79
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
0.25
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.04
Liver Injury II
Safe
hERG Blockers
Safe
Daphnia Maga
6.16
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
-3.18
Rat (Acute)
5.07
Rat (Chronic Oral)
1.73
Fathead Minnow
3.79
Respiratory Disease
Toxic
Skin Sensitisation
Toxic
SR-ARE
Safe
SR-ATAD5
Toxic
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Safe

General Properties

Boiling Point
386.42
Hydration Free Energy
-8.43
Log(D) at pH=7.4
-0.18
Log(P)
0.13
Log S
-2.33
Log(Vapor Pressure)
-7.49
Melting Point
152.31
pKa Acid
5.29
pKa Basic
2.09
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Adenylate cyclase type 5 P30803 ADCY5_CANLF Canis lupus familiaris 3 0.7283
Adenylate cyclase type 5 P30803 ADCY5_CANLF Canis lupus familiaris 3 0.7283
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.7088
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.7088

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