13-O-desacetyl-1beta-hydroxy-afraglaucolide - Compound Card

13-O-desacetyl-1beta-hydroxy-afraglaucolide

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13-O-desacetyl-1beta-hydroxy-afraglaucolide

Structure
Zoomed Structure
  • Family: Plantae - Asteraceae
  • Kingdom: Plantae
  • Class: Terpenoid
    • Subclass: Sesquiterpene Lactone
Canonical Smiles OCC1=C2CCC(=C)[C@H](O)C[C@@H](/C(=C/[C@H]2OC1=O)/C)OC(=O)C
InChI InChI=1S/C17H22O6/c1-9-4-5-12-13(8-18)17(21)23-16(12)6-10(2)15(7-14(9)20)22-11(3)19/h6,14-16,18,20H,1,4-5,7-8H2,2-3H3/b10-6+/t14-,15+,16-/m1/s1
InChIKey MCJAKNZUJXCHOQ-GXUCJDGASA-N
Formula C17H22O6
HBA 6
HBD 2
MW 322.36
Rotatable Bonds 2
TPSA 93.06
LogP 1.18
Number Rings 2
Number Aromatic Rings 0
Heavy Atom Count 23
Formal Charge 0
Fraction CSP3 0.53
Exact Mass 322.14
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Artemisia judaica Asteraceae Plantae 205369
2 Babcockia platylepsis Asteraceae Plantae 43189

Showing of synonyms

  • Mansour RMA, Saleh NAM, et al. (1983). A chemosystematic study of the phenolics of Sonchus.. Phytochemistry,1983,22(2),489-492. [View]
  • Khafagy SM, El-din AS, et al. (1988). Glaucolide-like sesquiterpene lactones from Artemisia judaica.. Phytochemistry,1988,27(4),1125-1128. [View]
Pubchem: 14021315
Nmrshiftdb2: 70031247

No compound-protein relationship available.

Structure

SMILES: C1CC(=C)CCCC=CC(C1=2)OC(=O)C2

Level: 0

Mol. Weight: 322.36 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.8
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.54
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.84

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
0.45
Plasma Protein Binding
35.06
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
6.3
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-0.62
Biodegradation
Toxic
Carcinogenesis
Toxic
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.26
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
5.14
Micronucleos
Toxic
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
-2.32
Rat (Acute)
2.57
Rat (Chronic Oral)
2.01
Fathead Minnow
4.12
Respiratory Disease
Safe
Skin Sensitisation
Toxic
SR-ARE
Safe
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Toxic

General Properties

Boiling Point
368.6
Hydration Free Energy
-10.59
Log(D) at pH=7.4
0.47
Log(P)
1.06
Log S
-1.92
Log(Vapor Pressure)
-7.04
Melting Point
137.81
pKa Acid
8.15
pKa Basic
4.43
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 3 0.8506
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 3 0.8506
Serpin domain-containing protein H0ZQY2 H0ZQY2_TAEGU Taeniopygia guttata 3 0.8260
Serpin domain-containing protein H0ZQY2 H0ZQY2_TAEGU Taeniopygia guttata 3 0.8260
Reaction center protein L chain P0C0Y7 RCEH_RHOSH Rhodobacter sphaeroides 3 0.8088
Reaction center protein L chain P0C0Y7 RCEH_RHOSH Rhodobacter sphaeroides 3 0.8088
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 3 0.7556
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 3 0.7556
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 3 0.7436
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 3 0.7436
Phospholipase A2, major isoenzyme P00592 PA21B_PIG Sus scrofa 3 0.7119
Phospholipase A2, major isoenzyme P00592 PA21B_PIG Sus scrofa 3 0.7119
Transcriptional activator, LuxR/UhpA family of regulators Q7NQP7 Q7NQP7_CHRVO Chromobacterium violaceum 3 0.7103
Transcriptional activator, LuxR/UhpA family of regulators Q7NQP7 Q7NQP7_CHRVO Chromobacterium violaceum 3 0.7103

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