Dehydrobrachylaenolide - Compound Card

Dehydrobrachylaenolide

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Dehydrobrachylaenolide

Structure
Zoomed Structure
  • Family: Plantae - Asteraceae
  • Kingdom: Plantae
  • Class: Terpenoid
    • Subclass: Sesquiterpene Lactone
Canonical Smiles O=C1C=C[C@]2([C@H](C1=C)[C@H]1OC(=O)C(=C)[C@@H]1CC2)C
InChI InChI=1S/C15H16O3/c1-8-10-4-6-15(3)7-5-11(16)9(2)12(15)13(10)18-14(8)17/h5,7,10,12-13H,1-2,4,6H2,3H3/t10-,12+,13-,15-/m0/s1
InChIKey GYBDKJQMRUKMGE-QJZXMWHDSA-N
Formula C15H16O3
HBA 3
HBD 0
MW 244.29
Rotatable Bonds 0
TPSA 43.37
LogP 2.2
Number Rings 3
Number Aromatic Rings 0
Heavy Atom Count 18
Formal Charge 0
Fraction CSP3 0.47
Exact Mass 244.11
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Dicoma anomala Asteraceae Plantae 1184223

Showing of synonyms

  • Becker JV, van der Merwe MM, et al. (2011). In vitro anti-plasmodial activity of Dicoma anomala subsp. Gerrardii (Asteraceae): identification of its main active constituent, structure-activity relationship studies and gene expression profiling. Malaria journal, 2011, 10, 295. [View]
Pubchem: 404548
Nmrshiftdb2: 20182415

No compound-protein relationship available.

Structure

SMILES: C=C1C(=O)OC(C12)C3C(CC2)C=CC(=O)C3=C

Level: 0

Mol. Weight: 244.29 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.68
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.400
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.18

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.670
Plasma Protein Binding
57.34
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
Substrate
CYP 2C9 Inhibitor
Non-Inhibitor
CYP 2C9 Substrate
Non-Substrate
CYP 2D6 Inhibitor
Non-Inhibitor
CYP 2D6 Substrate
Non-Substrate
CYP 3A4 Inhibitor
Inhibitor
CYP 3A4 Substrate
Non-Substrate
OATP1B1
Non-Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
10.120
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Toxic
Bioconcentration Factor
0.420
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.110
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
4.590
Micronucleos
Safe
NR-AhR
Safe
NR-AR
Safe
NR-AR-LBD
Toxic
NR-Aromatase
Safe
NR-ER
Safe
NR-ER-LBD
Safe
NR-GR
Safe
NR-PPAR-gamma
Safe
NR-TR
Safe
T. Pyriformis
1.680
Rat (Acute)
2.280
Rat (Chronic Oral)
1.860
Fathead Minnow
3.920
Respiratory Disease
Safe
Skin Sensitisation
Toxic
SR-ARE
Toxic
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Toxic

General Properties

Boiling Point
329.460
Hydration Free Energy
-5.240
Log(D) at pH=7.4
2.160
Log(P)
1.42
Log S
-3.12
Log(Vapor Pressure)
-5.18
Melting Point
160.08
pKa Acid
8.32
pKa Basic
5.83
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
ADP-ribosylation factor 1 P84080 ARF1_BOVIN Bos taurus 3 0.8029
Adenylate cyclase type 5 P30803 ADCY5_CANLF Canis lupus familiaris 3 0.7609
Abscisic acid receptor PYL2 O80992 PYL2_ARATH Arabidopsis thaliana 2 0.7080
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 2 0.7044

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