1beta,8alpha-dihydroxygermacr-4-en-12,6-olide - Compound Card

1beta,8alpha-dihydroxygermacr-4-en-12,6-olide

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1beta,8alpha-dihydroxygermacr-4-en-12,6-olide

Structure
Zoomed Structure
  • Family: Plantae - Asteraceae
  • Kingdom: Plantae
  • Class: Terpenoid
    • Subclass: Sesquiterpene Lactone
Canonical Smiles C/C/1=C\[C@H]2OC(=O)[C@H](C2[C@H](CC(=C)[C@@H](CC1)O)O)C
InChI InChI=1S/C15H22O4/c1-8-4-5-11(16)9(2)7-12(17)14-10(3)15(18)19-13(14)6-8/h6,10-14,16-17H,2,4-5,7H2,1,3H3/b8-6+/t10-,11+,12-,13+,14?/m0/s1
InChIKey GRUOWKYRKACQKC-KREIXESESA-N
Formula C15H22O4
HBA 4
HBD 2
MW 266.34
Rotatable Bonds 0
TPSA 66.76
LogP 1.57
Number Rings 2
Number Aromatic Rings 0
Heavy Atom Count 19
Formal Charge 0
Fraction CSP3 0.67
Exact Mass 266.15
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Artemisia herba-alba Asteraceae Plantae 72329

Showing of synonyms

  • Ahmed AA, Abou-El-Ela M, et al. (1990). Eudesmanolides and other constituents from Artemisia herba-alba.. Phytochemistry,1990,29(11),3661-3663. [View]
Pubchem: 14335250
Nmrshiftdb2: 60046258

No compound-protein relationship available.

Structure

SMILES: C1CC(=C)CCCC=CC(C12)OC(=O)C2

Level: 0

Mol. Weight: 266.34 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.89
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.26
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.49

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
0.46
Plasma Protein Binding
34.91
Steady State Volume of Distribution
-

Metabolism

Breast Cancer Resistance Protein
Non-Inhibitor
CYP 1A2 Inhibitor
Non-Inhibitor
CYP 1A2 Substrate
Non-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
6.12
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-0.39
Biodegradation
Toxic
Carcinogenesis
Toxic
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
-0.51
Liver Injury II
Safe
hERG Blockers
Safe
Daphnia Maga
3.86
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
-3.34
Rat (Acute)
3.04
Rat (Chronic Oral)
2.01
Fathead Minnow
3.92
Respiratory Disease
Toxic
Skin Sensitisation
Toxic
SR-ARE
Safe
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Safe

General Properties

Boiling Point
347.76
Hydration Free Energy
-10.56
Log(D) at pH=7.4
0.69
Log(P)
1.14
Log S
-1.85
Log(Vapor Pressure)
-6.4
Melting Point
139.2
pKa Acid
8.58
pKa Basic
5.07
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Iota toxin component Ia Q46220 Q46220_CLOPF Clostridium perfringens 3 0.8766
Iota toxin component Ia Q46220 Q46220_CLOPF Clostridium perfringens 3 0.8766
Transcriptional activator, LuxR/UhpA family of regulators Q7NQP7 Q7NQP7_CHRVO Chromobacterium violaceum 3 0.8400
Transcriptional activator, LuxR/UhpA family of regulators Q7NQP7 Q7NQP7_CHRVO Chromobacterium violaceum 3 0.8400
Liver carboxylesterase 1 P23141 EST1_HUMAN Homo sapiens 3 0.8303
Liver carboxylesterase 1 P23141 EST1_HUMAN Homo sapiens 3 0.8303
Succinate dehydrogenase [ubiquinone] flavoprotein subunit, mitochondrial Q0QF01 SDHA_PIG Sus scrofa 3 0.8274
Succinate dehydrogenase [ubiquinone] flavoprotein subunit, mitochondrial Q0QF01 SDHA_PIG Sus scrofa 3 0.8274
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 3 0.7837
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 3 0.7837
Lysozyme C II P11941 LYSC2_ONCMY Oncorhynchus mykiss 3 0.7390
Lysozyme C II P11941 LYSC2_ONCMY Oncorhynchus mykiss 3 0.7390
Regulatory protein SdiA P07026 SDIA_ECOLI Escherichia coli 3 0.7375
Regulatory protein SdiA P07026 SDIA_ECOLI Escherichia coli 3 0.7375
Reaction center protein L chain P0C0Y7 RCEH_RHOSH Rhodobacter sphaeroides 3 0.7369
Reaction center protein L chain P0C0Y7 RCEH_RHOSH Rhodobacter sphaeroides 3 0.7369
Transcriptional activator, LuxR/UhpA family of regulators Q7NQP7 Q7NQP7_CHRVO Chromobacterium violaceum 3 0.7329
Transcriptional activator, LuxR/UhpA family of regulators Q7NQP7 Q7NQP7_CHRVO Chromobacterium violaceum 3 0.7329
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 3 0.7282
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 3 0.7282
Vitamin D-binding protein P02774 VTDB_HUMAN Homo sapiens 2 0.7217
Vitamin D-binding protein P02774 VTDB_HUMAN Homo sapiens 2 0.7217
Adenylate cyclase type 5 P30803 ADCY5_CANLF Canis lupus familiaris 3 0.7214
Adenylate cyclase type 5 P30803 ADCY5_CANLF Canis lupus familiaris 3 0.7214
Peptide deformylase 1B, chloroplastic/mitochondrial Q9FUZ2 DEF1B_ARATH Arabidopsis thaliana 3 0.7175
Peptide deformylase 1B, chloroplastic/mitochondrial Q9FUZ2 DEF1B_ARATH Arabidopsis thaliana 3 0.7175

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