Iso-seco-tanapartholide-3-O-methyl ether - Compound Card

Iso-seco-tanapartholide-3-O-methyl ether

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Iso-seco-tanapartholide-3-O-methyl ether

Structure
Zoomed Structure
  • Family: Plantae - Asteraceae
  • Kingdom: Plantae
  • Class: Terpenoid
    • Subclass: Sesquiterpene Lactone
Canonical Smiles CO[C@H]1CC(=O)C(=C1C)[C@H]1OC(=O)C(=C)[C@@H]1CCC(=O)C
InChI InChI=1S/C16H20O5/c1-8(17)5-6-11-9(2)16(19)21-15(11)14-10(3)13(20-4)7-12(14)18/h11,13,15H,2,5-7H2,1,3-4H3/t11-,13-,15-/m0/s1
InChIKey YMBVLYVGHGDKHO-WHOFXGATSA-N
Formula C16H20O5
HBA 5
HBD 0
MW 292.33
Rotatable Bonds 5
TPSA 69.67
LogP 1.76
Number Rings 2
Number Aromatic Rings 0
Heavy Atom Count 21
Formal Charge 0
Fraction CSP3 0.56
Exact Mass 292.13
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Tanacetum sinaicum Asteraceae Plantae —

Showing of synonyms

  • Hegazy MEF, Hamed AR, et al. (2015). Anti-inflammatory sesquiterpenes from the medicinal herb Tanacetum sinaicum. RSC Advances,2015,5,44895-44901. [View]
Pubchem: 70697791
Chebi: 66090
Nmrshiftdb2: 60145353
Metabolights: MTBLC66090

No compound-protein relationship available.

Structure

SMILES: C=C1C(=O)OC(C1)C2=CCCC2=O

Level: 1

Mol. Weight: 292.33 g/mol

Structure

SMILES: C=C1C(=O)OCC1

Level: 0

Mol. Weight: 292.33 g/mol

Structure

SMILES: O=C1C=CCC1

Level: 0

Mol. Weight: 292.33 g/mol

Anti-inflammatory

Absorption

Caco-2 (logPapp)
-4.69
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.810
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.58

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.630
Plasma Protein Binding
46.93
Steady State Volume of Distribution
-

Metabolism

Breast Cancer Resistance Protein
Non-Inhibitor
CYP 1A2 Inhibitor
Non-Inhibitor
CYP 1A2 Substrate
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
8.340
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-0.380
Biodegradation
Toxic
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.370
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
5.540
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
Toxic
T. Pyriformis
-0.730
Rat (Acute)
3.160
Rat (Chronic Oral)
2.070
Fathead Minnow
4.190
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
358.200
Hydration Free Energy
-6.770
Log(D) at pH=7.4
0.840
Log(P)
0.26
Log S
-2.57
Log(Vapor Pressure)
-6.1
Melting Point
128.78
pKa Acid
7.1
pKa Basic
3.91
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Reaction center protein L chain P0C0Y7 RCEH_RHOSH Rhodobacter sphaeroides 3 0.8858
Reaction center protein L chain P0C0Y7 RCEH_RHOSH Rhodobacter sphaeroides 3 0.8858
Succinate dehydrogenase [ubiquinone] flavoprotein subunit, mitochondrial Q0QF01 SDHA_PIG Sus scrofa 3 0.8790
Succinate dehydrogenase [ubiquinone] flavoprotein subunit, mitochondrial Q0QF01 SDHA_PIG Sus scrofa 3 0.8790
Trichothecene 15-O-acetyltransferase TRI3 Q9C1B7 TRI3_FUSSP Fusarium sporotrichioides 3 0.8733
Trichothecene 15-O-acetyltransferase TRI3 Q9C1B7 TRI3_FUSSP Fusarium sporotrichioides 3 0.8733
ADP-ribosylation factor 1 P84077 ARF1_HUMAN Homo sapiens 2 0.8391
ADP-ribosylation factor 1 P84077 ARF1_HUMAN Homo sapiens 2 0.8391
ADP-ribosylation factor 1 P84080 ARF1_BOVIN Bos taurus 3 0.7858
ADP-ribosylation factor 1 P84080 ARF1_BOVIN Bos taurus 3 0.7858
Regulatory protein SdiA P07026 SDIA_ECOLI Escherichia coli 3 0.7540
Regulatory protein SdiA P07026 SDIA_ECOLI Escherichia coli 3 0.7540
Adenylate cyclase type 5 P30803 ADCY5_CANLF Canis lupus familiaris 3 0.7482
Adenylate cyclase type 5 P30803 ADCY5_CANLF Canis lupus familiaris 3 0.7482
Liver carboxylesterase 1 P23141 EST1_HUMAN Homo sapiens 2 0.7459
Liver carboxylesterase 1 P23141 EST1_HUMAN Homo sapiens 2 0.7459
Adenylate cyclase type 5 P30803 ADCY5_CANLF Canis lupus familiaris 3 0.7415
Adenylate cyclase type 5 P30803 ADCY5_CANLF Canis lupus familiaris 3 0.7415
Avidin P02701 AVID_CHICK Gallus gallus 2 0.7289
Avidin P02701 AVID_CHICK Gallus gallus 2 0.7289
TamL D3Y1I2 D3Y1I2_9ACTN Streptomyces sp. 307-9 2 0.7282
TamL D3Y1I2 D3Y1I2_9ACTN Streptomyces sp. 307-9 2 0.7282
Type IV / VI secretion system DotU domain-containing protein Q9KN50 Q9KN50_VIBCH Vibrio cholerae serotype O1 2 0.7215
Type IV / VI secretion system DotU domain-containing protein Q9KN50 Q9KN50_VIBCH Vibrio cholerae serotype O1 2 0.7215
Adenylate cyclase type 5 P30803 ADCY5_CANLF Canis lupus familiaris 3 0.7199
Adenylate cyclase type 5 P30803 ADCY5_CANLF Canis lupus familiaris 3 0.7199

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