1-oxo-9beta-acetoxygermacra-4,10(14)-dien-6beta,11betaH-12,6-olide - Compound Card

1-oxo-9beta-acetoxygermacra-4,10(14)-dien-6beta,11betaH-12,6-olide

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1-oxo-9beta-acetoxygermacra-4,10(14)-dien-6beta,11betaH-12,6-olide

Structure
Zoomed Structure
  • Family: Plantae - Asteraceae
  • Kingdom: Plantae
  • Class: Terpenoid
    • Subclass: Sesquiterpene Lactone
Canonical Smiles CC(=O)OC1CC2[C@@H](/C=C(/CCC(=O)C1=C)\C)OC(=O)[C@H]2C
InChI InChI=1S/C17H22O5/c1-9-5-6-14(19)11(3)15(21-12(4)18)8-13-10(2)17(20)22-16(13)7-9/h7,10,13,15-16H,3,5-6,8H2,1-2,4H3/b9-7+/t10-,13?,15?,16+/m0/s1
InChIKey XDNDSYBYMNPMAI-JQPVKVASSA-N
Formula C17H22O5
HBA 5
HBD 0
MW 306.36
Rotatable Bonds 1
TPSA 69.67
LogP 2.35
Number Rings 2
Number Aromatic Rings 0
Heavy Atom Count 22
Formal Charge 0
Fraction CSP3 0.59
Exact Mass 306.15
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Artemisia herba-alba Asteraceae Plantae 72329

Showing of synonyms

  • Mako JA, Sanz-Cervera JF, et al. (1994). New germacranolides and eudesmanolides from North African Artemisia herba-alba.. Journal of Natural Products,1994,57(7),939-946. [View]
Pubchem: 163051375
Nmrshiftdb2: 60074969

No compound-protein relationship available.

Structure

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

Level: 0

Mol. Weight: 306.36 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.66
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.6
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.41

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.5
Plasma Protein Binding
47.3
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
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
9.74
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
0.14
Biodegradation
Toxic
Carcinogenesis
Toxic
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.83
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
5.37
Micronucleos
Toxic
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
0.63
Rat (Acute)
2.73
Rat (Chronic Oral)
1.93
Fathead Minnow
4.28
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
341.0
Hydration Free Energy
-6.51
Log(D) at pH=7.4
1.34
Log(P)
1.8
Log S
-2.7
Log(Vapor Pressure)
-5.81
Melting Point
91.53
pKa Acid
10.2
pKa Basic
4.49
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.8036
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.8036
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 3 0.7887
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 3 0.7887
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.7792
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.7792
Succinate dehydrogenase [ubiquinone] flavoprotein subunit, mitochondrial Q0QF01 SDHA_PIG Sus scrofa 3 0.7701
Succinate dehydrogenase [ubiquinone] flavoprotein subunit, mitochondrial Q0QF01 SDHA_PIG Sus scrofa 3 0.7701
Type IV / VI secretion system DotU domain-containing protein Q9KN50 Q9KN50_VIBCH Vibrio cholerae serotype O1 2 0.7697
Type IV / VI secretion system DotU domain-containing protein Q9KN50 Q9KN50_VIBCH Vibrio cholerae serotype O1 2 0.7697
Peptidyl-prolyl cis-trans isomerase FKBP1A P62942 FKB1A_HUMAN Homo sapiens 3 0.7672
Peptidyl-prolyl cis-trans isomerase FKBP1A P62942 FKB1A_HUMAN Homo sapiens 3 0.7672
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 3 0.7644
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 3 0.7644
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 3 0.7633
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 3 0.7633
Adenylate cyclase type 5 P30803 ADCY5_CANLF Canis lupus familiaris 3 0.7554
Adenylate cyclase type 5 P30803 ADCY5_CANLF Canis lupus familiaris 3 0.7554
Liver carboxylesterase 1 P23141 EST1_HUMAN Homo sapiens 2 0.7365
Liver carboxylesterase 1 P23141 EST1_HUMAN Homo sapiens 2 0.7365
N-alpha-acetyltransferase 50 Q9GZZ1 NAA50_HUMAN Homo sapiens 3 0.7324
N-alpha-acetyltransferase 50 Q9GZZ1 NAA50_HUMAN Homo sapiens 3 0.7324
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7128
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7128
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 2 0.7119
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 2 0.7119
Adenylate cyclase type 5 P30803 ADCY5_CANLF Canis lupus familiaris 3 0.7098
Adenylate cyclase type 5 P30803 ADCY5_CANLF Canis lupus familiaris 3 0.7098
Adenylate cyclase type 5 P30803 ADCY5_CANLF Canis lupus familiaris 3 0.7020
Adenylate cyclase type 5 P30803 ADCY5_CANLF Canis lupus familiaris 3 0.7020

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