8alpha-hydroxy-3-oxo-6betaH,7alphaH,11betaH-germacran-4(14),9(10)-dien-6,12-olide - Compound Card

8alpha-hydroxy-3-oxo-6betaH,7alphaH,11betaH-germacran-4(14),9(10)-dien-6,12-olide

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8alpha-hydroxy-3-oxo-6betaH,7alphaH,11betaH-germacran-4(14),9(10)-dien-6,12-olide

Structure
Zoomed Structure
  • Family: Plantae - Asteraceae
  • Kingdom: Plantae
  • Class: Terpenoid
    • Subclass: Sesquiterpene Lactone
Canonical Smiles C/C/1=C\[C@H](O)C2[C@@H](CC(=C)C(=O)CC1)OC(=O)[C@H]2C
InChI InChI=1S/C15H20O4/c1-8-4-5-11(16)9(2)7-13-14(12(17)6-8)10(3)15(18)19-13/h6,10,12-14,17H,2,4-5,7H2,1,3H3/b8-6+/t10-,12-,13+,14?/m0/s1
InChIKey KBOUOSQJTWOYPP-CNOPUJIASA-N
Formula C15H20O4
HBA 4
HBD 1
MW 264.32
Rotatable Bonds 0
TPSA 63.6
LogP 1.78
Number Rings 2
Number Aromatic Rings 0
Heavy Atom Count 19
Formal Charge 0
Fraction CSP3 0.6
Exact Mass 264.14
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Artemisia herba-alba Asteraceae Plantae 72329

Showing of synonyms

  • Gordon MM, Van Derveer D, et al. (1981). New germacranolides from Artemisia herba alba. X-ray crystal structures of 3beta,8alpha-dihydroxy-6betaH,7alphaH,11betaH-germacran-4(14),9(10)-dien-6,12-olide and the corresponding 3-oxo-olide.. Journal of Natural Products,1981,44(4),432-440. [View]
Pubchem: 162937346

No compound-protein relationship available.

Structure

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

Level: 0

Mol. Weight: 264.32 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.7
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.42
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.5

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.5
Plasma Protein Binding
40.91
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
6.7
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-0.33
Biodegradation
Toxic
Carcinogenesis
Toxic
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.43
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
4.31
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
-1.25
Rat (Acute)
2.99
Rat (Chronic Oral)
1.89
Fathead Minnow
4.0
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
332.29
Hydration Free Energy
-9.03
Log(D) at pH=7.4
0.9
Log(P)
1.02
Log S
-1.76
Log(Vapor Pressure)
-6.1
Melting Point
128.71
pKa Acid
9.25
pKa Basic
4.15
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Succinate dehydrogenase [ubiquinone] flavoprotein subunit, mitochondrial Q0QF01 SDHA_PIG Sus scrofa 3 0.8831
Succinate dehydrogenase [ubiquinone] flavoprotein subunit, mitochondrial Q0QF01 SDHA_PIG Sus scrofa 3 0.8831
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 3 0.8078
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 3 0.8078
Trichothecene 15-O-acetyltransferase TRI3 Q9C1B7 TRI3_FUSSP Fusarium sporotrichioides 3 0.7955
Trichothecene 15-O-acetyltransferase TRI3 Q9C1B7 TRI3_FUSSP Fusarium sporotrichioides 3 0.7955
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 3 0.7889
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 3 0.7889
Reaction center protein L chain P0C0Y7 RCEH_RHOSH Rhodobacter sphaeroides 3 0.7758
Reaction center protein L chain P0C0Y7 RCEH_RHOSH Rhodobacter sphaeroides 3 0.7758
ADP-ribosylation factor 1 P84080 ARF1_BOVIN Bos taurus 3 0.7599
ADP-ribosylation factor 1 P84080 ARF1_BOVIN Bos taurus 3 0.7599
Alpha/beta hydrolase fold protein D2J2T6 D2J2T6_9RHIZ Ochrobactrum sp. T63 3 0.7536
Alpha/beta hydrolase fold protein D2J2T6 D2J2T6_9RHIZ Ochrobactrum sp. T63 3 0.7536
Adenylate cyclase type 5 P30803 ADCY5_CANLF Canis lupus familiaris 3 0.7479
Adenylate cyclase type 5 P30803 ADCY5_CANLF Canis lupus familiaris 3 0.7479
N-alpha-acetyltransferase 50 Q9GZZ1 NAA50_HUMAN Homo sapiens 3 0.7459
N-alpha-acetyltransferase 50 Q9GZZ1 NAA50_HUMAN Homo sapiens 3 0.7459
Type IV / VI secretion system DotU domain-containing protein Q9KN50 Q9KN50_VIBCH Vibrio cholerae serotype O1 2 0.7453
Type IV / VI secretion system DotU domain-containing protein Q9KN50 Q9KN50_VIBCH Vibrio cholerae serotype O1 2 0.7453
Abscisic acid receptor PYL2 O80992 PYL2_ARATH Arabidopsis thaliana 2 0.7356
Abscisic acid receptor PYL2 O80992 PYL2_ARATH Arabidopsis thaliana 2 0.7356
Ferrichrome outer membrane transporter/phage receptor P06971 FHUA_ECOLI Escherichia coli 3 0.7286
Ferrichrome outer membrane transporter/phage receptor P06971 FHUA_ECOLI Escherichia coli 3 0.7286
Adenylate cyclase type 5 P30803 ADCY5_CANLF Canis lupus familiaris 4 0.7262
Adenylate cyclase type 5 P30803 ADCY5_CANLF Canis lupus familiaris 4 0.7262
Chitinase Q54276 Q54276_SERMA Serratia marcescens 3 0.7179
Chitinase Q54276 Q54276_SERMA Serratia marcescens 3 0.7179
Streptavidin P22629 SAV_STRAV Streptomyces avidinii 3 0.7130
Streptavidin P22629 SAV_STRAV Streptomyces avidinii 3 0.7130
ADP-ribosylation factor 1 P84077 ARF1_HUMAN Homo sapiens 2 0.7073
ADP-ribosylation factor 1 P84077 ARF1_HUMAN Homo sapiens 2 0.7073
Liver carboxylesterase 1 P23141 EST1_HUMAN Homo sapiens 2 0.7048
Liver carboxylesterase 1 P23141 EST1_HUMAN Homo sapiens 2 0.7048

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