Filifolide A - Compound Card

Filifolide A

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Filifolide A

Structure
Zoomed Structure
  • Family: Plantae - Asteraceae
  • Kingdom: Plantae
  • Class: Terpenoid
    • Subclass: Monoterpene Lactone
Canonical Smiles O=C1O[C@H]2C[C@@H]1C(C)(C)C=C2C
InChI InChI=1S/C10H14O2/c1-6-5-10(2,3)7-4-8(6)12-9(7)11/h5,7-8H,4H2,1-3H3/t7-,8-/m0/s1
InChIKey JHKNAYGQYUKKDQ-YUMQZZPRSA-N
Formula C10H14O2
HBA 2
HBD 0
MW 166.22
Rotatable Bonds 0
TPSA 26.3
LogP 1.9
Number Rings 2
Number Aromatic Rings 0
Heavy Atom Count 12
Formal Charge 0
Fraction CSP3 0.7
Exact Mass 166.1
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Amberboa tubuliflora Asteraceae Plantae 1284450
2 Achillea ligustica Asteraceae Plantae 282745

Showing of synonyms

  • Ahmed AA, El-Ela MA, et al. (1990). A guaianolide from Amberboa tubuliflora. Phytochemistry,1990,29(12),3946-3947. [View]
  • Boudjerda A, Zater H, et al. (2008). A new guaianolide and other constituents from Achillea ligustica.. Biochemical Systematics and Ecology,2008,36,461-466. [View]
Pubchem: 90472998
Nmrshiftdb2: 60145761

No compound-protein relationship available.

Structure

SMILES: C12C(=O)OC(C1)C=CC2

Level: 0

Mol. Weight: 166.22 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.9
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.1
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.27

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.37
Plasma Protein Binding
31.66
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
Substrate
CYP 2D6 Inhibitor
Non-Inhibitor
CYP 2D6 Substrate
Substrate
CYP 3A4 Inhibitor
Non-Inhibitor
CYP 3A4 Substrate
Substrate
OATP1B1
Non-Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
8.45
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
1.0
Biodegradation
Toxic
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Toxic
Maximum Tolerated Dose
0.6
Liver Injury II
Safe
hERG Blockers
Safe
Daphnia Maga
3.72
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
0.53
Rat (Acute)
2.19
Rat (Chronic Oral)
1.58
Fathead Minnow
3.67
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
236.8
Hydration Free Energy
-4.37
Log(D) at pH=7.4
1.95
Log(P)
1.87
Log S
-2.25
Log(Vapor Pressure)
-1.09
Melting Point
26.97
pKa Acid
10.39
pKa Basic
5.46
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.8715
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.8715
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7740
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7740
Abscisic acid receptor PYL2 O80992 PYL2_ARATH Arabidopsis thaliana 2 0.7730
Abscisic acid receptor PYL2 O80992 PYL2_ARATH Arabidopsis thaliana 2 0.7730
Abscisic acid receptor PYR1 O49686 PYR1_ARATH Arabidopsis thaliana 3 0.7492
Abscisic acid receptor PYR1 O49686 PYR1_ARATH Arabidopsis thaliana 3 0.7492
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7469
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7469
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7457
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7457
Abscisic acid receptor PYL3 Q9SSM7 PYL3_ARATH Arabidopsis thaliana 3 0.7419
Abscisic acid receptor PYL3 Q9SSM7 PYL3_ARATH Arabidopsis thaliana 3 0.7419
Abscisic acid receptor PYR1 O49686 PYR1_ARATH Arabidopsis thaliana 3 0.7340
Abscisic acid receptor PYR1 O49686 PYR1_ARATH Arabidopsis thaliana 3 0.7340
Progesterone receptor P06401 PRGR_HUMAN Homo sapiens 2 0.7339
Progesterone receptor P06401 PRGR_HUMAN Homo sapiens 2 0.7339
Cytochrome P450 monooxygenase Q5YNS8 Q5YNS8_NOCFA Nocardia farcinica 2 0.7278
Cytochrome P450 monooxygenase Q5YNS8 Q5YNS8_NOCFA Nocardia farcinica 2 0.7278
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.7237
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.7237
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 2 0.7165
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 2 0.7165
Camphor 5-monooxygenase P00183 CPXA_PSEPU Pseudomonas putida 3 0.7146
Camphor 5-monooxygenase P00183 CPXA_PSEPU Pseudomonas putida 3 0.7146
Nuclear receptor subfamily 1 group I member 3 O35627 NR1I3_MOUSE Mus musculus 2 0.7119
Nuclear receptor subfamily 1 group I member 3 O35627 NR1I3_MOUSE Mus musculus 2 0.7119
Gastrotropin Q6IMW5 Q6IMW5_DANRE Danio rerio 2 0.7087
Gastrotropin Q6IMW5 Q6IMW5_DANRE Danio rerio 2 0.7087
Nuclear receptor ROR-beta P45446 RORB_RAT Rattus norvegicus 2 0.7081
Nuclear receptor ROR-beta P45446 RORB_RAT Rattus norvegicus 2 0.7081
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7029
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7029
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7009
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7009
Cytochrome P450 monooxygenase Q5YNS8 Q5YNS8_NOCFA Nocardia farcinica 2 0.7004
Cytochrome P450 monooxygenase Q5YNS8 Q5YNS8_NOCFA Nocardia farcinica 2 0.7004

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