Tanacetolide B - Compound Card

Tanacetolide B

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Tanacetolide B

Structure
Zoomed Structure
  • Family: Plantae - Asteraceae
  • Kingdom: Plantae
  • Class: Terpenoid
    • Subclass: Sesquiterpene
Canonical Smiles CCCCCCCCCCCCCCCC/C=C/[C@@H]([C@H](NC(=O)C)CO)O
InChI InChI=1S/C23H45NO3/c1-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-23(27)22(20-25)24-21(2)26/h18-19,22-23,25,27H,3-17,20H2,1-2H3,(H,24,26)/b19-18+/t22-,23+/m1/s1
InChIKey NSOQQZAUFCNZHQ-GWGOZDFZSA-N
Formula C23H45NO3
HBA 3
HBD 3
MW 383.62
Rotatable Bonds 19
TPSA 69.56
LogP 5.27
Number Rings 0
Number Aromatic Rings 0
Heavy Atom Count 27
Formal Charge 0
Fraction CSP3 0.87
Exact Mass 383.34
Number of Lipinski Rule Violations 1
# 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: 11292035
Nmrshiftdb2: 60145364

No compound-protein relationship available.

No scaffolds available.

Anti-inflammatory

Absorption

Caco-2 (logPapp)
-5.55
Human Oral Bioavailability 20%
Non-Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-3.96
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Substrate
Skin Permeability
-3.06

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
1.84
Plasma Protein Binding
50.98
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
Inhibitor
CYP 2C9 Substrate
Non-Substrate
CYP 2D6 Inhibitor
Inhibitor
CYP 2D6 Substrate
Non-Substrate
CYP 3A4 Inhibitor
Non-Inhibitor
CYP 3A4 Substrate
Non-Substrate
OATP1B1
Non-Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
1.56
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Safe
Bioconcentration Factor
0.16
Biodegradation
Toxic
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
1.49
Liver Injury II
Safe
hERG Blockers
Safe
Daphnia Maga
3.8
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
0.36
Rat (Acute)
1.77
Rat (Chronic Oral)
2.81
Fathead Minnow
4.11
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
452.12
Hydration Free Energy
-8.43
Log(D) at pH=7.4
3.9
Log(P)
7.02
Log S
-5.22
Log(Vapor Pressure)
-9.79
Melting Point
81.87
pKa Acid
10.21
pKa Basic
5.63
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Actin, alpha skeletal muscle P68135 ACTS_RABIT Oryctolagus cuniculus 3 0.9957
Actin, alpha skeletal muscle P68135 ACTS_RABIT Oryctolagus cuniculus 3 0.9957
Iota toxin component Ia Q46220 Q46220_CLOPF Clostridium perfringens 3 0.9955
Iota toxin component Ia Q46220 Q46220_CLOPF Clostridium perfringens 3 0.9955
Actin, alpha skeletal muscle P68135 ACTS_RABIT Oryctolagus cuniculus 3 0.9745
Actin, alpha skeletal muscle P68135 ACTS_RABIT Oryctolagus cuniculus 3 0.9745
Actin, alpha skeletal muscle P68135 ACTS_RABIT Oryctolagus cuniculus 3 0.9688
Actin, alpha skeletal muscle P68135 ACTS_RABIT Oryctolagus cuniculus 3 0.9688
Actin, alpha skeletal muscle P68135 ACTS_RABIT Oryctolagus cuniculus 3 0.9642
Actin, alpha skeletal muscle P68135 ACTS_RABIT Oryctolagus cuniculus 3 0.9642
Macrophage metalloelastase P39900 MMP12_HUMAN Homo sapiens 3 0.9323
Macrophage metalloelastase P39900 MMP12_HUMAN Homo sapiens 3 0.9323
Methionine aminopeptidase 2 P9WK19 MAP12_MYCTU Mycobacterium tuberculosis 3 0.9212
Methionine aminopeptidase 2 P9WK19 MAP12_MYCTU Mycobacterium tuberculosis 3 0.9212
Aldos-2-ulose dehydratase P84193 AUD_PHACH Phanerodontia chrysosporium 3 0.9089
Aldos-2-ulose dehydratase P84193 AUD_PHACH Phanerodontia chrysosporium 3 0.9089
Glucosidase II subunit alpha Q9STC1 Q9STC1_GRALE Gracilariopsis lemaneiformis 3 0.8489
Glucosidase II subunit alpha Q9STC1 Q9STC1_GRALE Gracilariopsis lemaneiformis 3 0.8489
Purine nucleoside phosphorylase DeoD-type P0ABP8 DEOD_ECOLI Escherichia coli 3 0.7986
Purine nucleoside phosphorylase DeoD-type P0ABP8 DEOD_ECOLI Escherichia coli 3 0.7986
Xylose isomerase P12070 XYLA_ARTS7 Arthrobacter sp 3 0.7551
Xylose isomerase P12070 XYLA_ARTS7 Arthrobacter sp 3 0.7551
Iota toxin component Ia Q46220 Q46220_CLOPF Clostridium perfringens 3 0.7306
Iota toxin component Ia Q46220 Q46220_CLOPF Clostridium perfringens 3 0.7306
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 2 0.7280
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 2 0.7280
Actin, alpha skeletal muscle P68135 ACTS_RABIT Oryctolagus cuniculus 3 0.7227
Actin, alpha skeletal muscle P68135 ACTS_RABIT Oryctolagus cuniculus 3 0.7227
Actin, alpha skeletal muscle P68135 ACTS_RABIT Oryctolagus cuniculus 3 0.7188
Actin, alpha skeletal muscle P68135 ACTS_RABIT Oryctolagus cuniculus 3 0.7188
Tachylectin-2 Q27084 TAL2_TACTR Tachypleus tridentatus 3 0.7179
Tachylectin-2 Q27084 TAL2_TACTR Tachypleus tridentatus 3 0.7179
Iota toxin component Ia Q46220 Q46220_CLOPF Clostridium perfringens 3 0.7152
Iota toxin component Ia Q46220 Q46220_CLOPF Clostridium perfringens 3 0.7152
Iota toxin component Ia Q46220 Q46220_CLOPF Clostridium perfringens 3 0.7148
Iota toxin component Ia Q46220 Q46220_CLOPF Clostridium perfringens 3 0.7148
Actin, alpha skeletal muscle P68135 ACTS_RABIT Oryctolagus cuniculus 3 0.7111
Actin, alpha skeletal muscle P68135 ACTS_RABIT Oryctolagus cuniculus 3 0.7111
Prolyl tripeptidyl peptidase Q7MUW6 PTP_PORGI Porphyromonas gingivalis 2 0.7037
Prolyl tripeptidyl peptidase Q7MUW6 PTP_PORGI Porphyromonas gingivalis 2 0.7037

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