Bakkenolide A - Compound Card

Bakkenolide A

Select a section from the left sidebar

Bakkenolide A

Structure
Zoomed Structure
  • Family: Plantae - Asteraceae
  • Kingdom: Plantae
  • Class: Terpenoid
    • Subclass: Sesquiterpene Lactone
Canonical Smiles C[C@H]1CCC[C@H]2[C@]1(C)C[C@@]1(C2)C(=O)OCC1=C
InChI InChI=1S/C15H22O2/c1-10-5-4-6-12-7-15(9-14(10,12)3)11(2)8-17-13(15)16/h10,12H,2,4-9H2,1,3H3/t10-,12+,14+,15+/m0/s1
InChIKey OVXAYHNZXBOVPV-QMGNLALYSA-N
Formula C15H22O2
HBA 2
HBD 0
MW 234.34
Rotatable Bonds 0
TPSA 26.3
LogP 3.32
Number Rings 3
Number Aromatic Rings 0
Heavy Atom Count 17
Formal Charge 0
Fraction CSP3 0.8
Exact Mass 234.16
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Hertia cheirifolia Asteraceae Plantae 430993
2 Hertia cheirifolia Asteraceae Plantae 430993

Showing of synonyms

  • Aclinou P, Benkouider A, et al. (1991). Eremophilenolides from Hertia cheirifolia. Phytochemistry,1991,30(6),2083-2084. [View]
  • Ammar S, Edziri H, et al. (2009). Spasmolytic and anti-inflammatory effects of constituents from Hertia cheirifolia. Phytomedicine,2009,16,1156-1161. [View] [PubMed]
Pubchem: 442173
Kegg Ligand: C09350
Chebi: 2984
Nmrshiftdb2: 70002604
CPRiL: 169726
Structure

SMILES: O=C1OCC(=C)C12CC3C(C2)CCCC3

Level: 0

Mol. Weight: 234.34 g/mol

Anti-inflammatory
Spasmolytic

Absorption

Caco-2 (logPapp)
-4.73
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.66
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.6

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.89
Plasma Protein Binding
50.55
Steady State Volume of Distribution
-

Metabolism

Breast Cancer Resistance Protein
Non-Inhibitor
CYP 1A2 Inhibitor
Inhibitor
CYP 1A2 Substrate
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
Inhibitor
CYP 3A4 Substrate
Non-Substrate
OATP1B1
Non-Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
11.15
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
0.74
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Toxic
Maximum Tolerated Dose
-0.61
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
4.03
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
0.01
Rat (Acute)
2.23
Rat (Chronic Oral)
1.65
Fathead Minnow
3.92
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
325.5
Hydration Free Energy
-2.97
Log(D) at pH=7.4
3.34
Log(P)
3.09
Log S
-4.23
Log(Vapor Pressure)
-4.07
Melting Point
91.05
pKa Acid
9.39
pKa Basic
6.7
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Sex hormone-binding globulin P04278 SHBG_HUMAN Homo sapiens 3 0.8314
Sex hormone-binding globulin P04278 SHBG_HUMAN Homo sapiens 3 0.8314
Sex hormone-binding globulin P04278 SHBG_HUMAN Homo sapiens 3 0.8174
Sex hormone-binding globulin P04278 SHBG_HUMAN Homo sapiens 3 0.8174
Gastrotropin Q6IMW5 Q6IMW5_DANRE Danio rerio 2 0.7696
Gastrotropin Q6IMW5 Q6IMW5_DANRE Danio rerio 2 0.7696
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7403
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7403
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 2 0.7362
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 2 0.7362
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 2 0.7348
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 2 0.7348
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7300
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7300
Sulfotransferase 2A1 Q06520 ST2A1_HUMAN Homo sapiens 2 0.7209
Sulfotransferase 2A1 Q06520 ST2A1_HUMAN Homo sapiens 2 0.7209
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7197
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7197
Corticosteroid-binding globulin P08185 CBG_HUMAN Homo sapiens 2 0.7166
Corticosteroid-binding globulin P08185 CBG_HUMAN Homo sapiens 2 0.7166
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7152
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7152
Abscisic acid receptor PYL9 Q84MC7 PYL9_ARATH Arabidopsis thaliana 2 0.7140
Abscisic acid receptor PYL9 Q84MC7 PYL9_ARATH Arabidopsis thaliana 2 0.7140
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7108
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7108
Type IV / VI secretion system DotU domain-containing protein Q9KN50 Q9KN50_VIBCH Vibrio cholerae serotype O1 2 0.7106
Type IV / VI secretion system DotU domain-containing protein Q9KN50 Q9KN50_VIBCH Vibrio cholerae serotype O1 2 0.7106
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 3 0.7083
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 3 0.7083

Download SDF