13-O-desacetyl-1-oxo-afraglaucolide - Compound Card

13-O-desacetyl-1-oxo-afraglaucolide

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13-O-desacetyl-1-oxo-afraglaucolide

Structure
Zoomed Structure
  • Family: Plantae - Asteraceae
  • Kingdom: Plantae
  • Class: Terpenoid
    • Subclass: Sesquiterpene Lactone
Canonical Smiles OCC1=C2CCC(=C)C(=O)C[C@H](/C(=C\[C@H]2OC1=O)/C)OC(=O)C
InChI InChI=1S/C17H20O6/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/h6,15-16,18H,1,4-5,7-8H2,2-3H3/b10-6-/t15-,16-/m1/s1
InChIKey BPBLQZHCVCIWBH-KETLTQCKSA-N
Formula C17H20O6
HBA 6
HBD 1
MW 320.34
Rotatable Bonds 2
TPSA 89.9
LogP 1.39
Number Rings 2
Number Aromatic Rings 0
Heavy Atom Count 23
Formal Charge 0
Fraction CSP3 0.47
Exact Mass 320.13
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Achillea fragrantissima Asteraceae Plantae 282738

Showing of synonyms

  • Abdel-Mogib M, Jakupovic J, et al. (1989). Glaucolides from Achillea fragrantissima.. Phytochemistry,1989,28(12),3528-3530. [View]
Pubchem: 162951084
Nmrshiftdb2: 70069988

No compound-protein relationship available.

Structure

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

Level: 0

Mol. Weight: 320.34 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.71
Human Oral Bioavailability 20%
Non-Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.59
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.87

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
0.47
Plasma Protein Binding
44.4
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
6.21
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-0.63
Biodegradation
Toxic
Carcinogenesis
Toxic
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.76
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
5.34
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
0.02
Rat (Acute)
2.36
Rat (Chronic Oral)
2.01
Fathead Minnow
4.17
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
371.45
Hydration Free Energy
-9.3
Log(D) at pH=7.4
0.99
Log(P)
1.17
Log S
-2.33
Log(Vapor Pressure)
-6.84
Melting Point
124.14
pKa Acid
8.22
pKa Basic
4.31
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Carbonic anhydrase 1 P00915 CAH1_HUMAN Homo sapiens 3 0.8629
Carbonic anhydrase 1 P00915 CAH1_HUMAN Homo sapiens 3 0.8629
Serpin domain-containing protein H0ZQY2 H0ZQY2_TAEGU Taeniopygia guttata 3 0.8201
Serpin domain-containing protein H0ZQY2 H0ZQY2_TAEGU Taeniopygia guttata 3 0.8201
Succinate dehydrogenase [ubiquinone] flavoprotein subunit, mitochondrial Q0QF01 SDHA_PIG Sus scrofa 3 0.8117
Succinate dehydrogenase [ubiquinone] flavoprotein subunit, mitochondrial Q0QF01 SDHA_PIG Sus scrofa 3 0.8117
11-beta-hydroxysteroid dehydrogenase 1 P28845 DHI1_HUMAN Homo sapiens 3 0.7382
11-beta-hydroxysteroid dehydrogenase 1 P28845 DHI1_HUMAN Homo sapiens 3 0.7382
Cytochrome P450 Q93H81 Q93H81_STRAX Streptomyces avermitilis 3 0.7326
Cytochrome P450 Q93H81 Q93H81_STRAX Streptomyces avermitilis 3 0.7326
Macrophage metalloelastase P39900 MMP12_HUMAN Homo sapiens 3 0.7256
Macrophage metalloelastase P39900 MMP12_HUMAN Homo sapiens 3 0.7256
Cysteine synthase P45040 CYSK_HAEIN Haemophilus influenzae 3 0.7221
Cysteine synthase P45040 CYSK_HAEIN Haemophilus influenzae 3 0.7221
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 3 0.7090
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 3 0.7090

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