8alpha,13-diacetoxy-1alpha-hydroxygermacra-4E,7(11),9Z-trien-6alpha,12-olide - Compound Card

8alpha,13-diacetoxy-1alpha-hydroxygermacra-4E,7(11),9Z-trien-6alpha,12-olide

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8alpha,13-diacetoxy-1alpha-hydroxygermacra-4E,7(11),9Z-trien-6alpha,12-olide

Structure
Zoomed Structure
  • Family: Plantae - Asteraceae
  • Kingdom: Plantae
  • Class: Terpenoid
    • Subclass: Sesquiterpene Lactone
Canonical Smiles CC(=O)O[C@H]1/C=C(/C)\[C@@H](O)CC/C(=C/[C@@H]2C1=C(COC(=O)C)C(=O)O2)/C
InChI InChI=1S/C19H24O7/c1-10-5-6-15(22)11(2)8-17(25-13(4)21)18-14(9-24-12(3)20)19(23)26-16(18)7-10/h7-8,15-17,22H,5-6,9H2,1-4H3/b10-7+,11-8-/t15-,16+,17-/m0/s1
InChIKey PTNBEYQHWBDDAI-FUQMODQDSA-N
Formula C19H24O7
HBA 7
HBD 1
MW 364.39
Rotatable Bonds 3
TPSA 99.13
LogP 1.75
Number Rings 2
Number Aromatic Rings 0
Heavy Atom Count 26
Formal Charge 0
Fraction CSP3 0.53
Exact Mass 364.15
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Cotula cinerea Asteraceae Plantae —

Showing of synonyms

  • Metwally MA, El-dahmy S, et al. (1986). Glaucolide-like sesquiterpene lactones from Cotula cinerea. Phytochemistry,1986,25(1),255-257. [View]
Pubchem: 163019889
Nmrshiftdb2: 70018558

No compound-protein relationship available.

Structure

SMILES: C1C(=O)OC(C=12)C=CCCCC=CC2

Level: 0

Mol. Weight: 364.39 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.69
Human Oral Bioavailability 20%
Non-Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.62
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-3.02

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.35
Plasma Protein Binding
42.3
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
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
7.56
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-0.09
Biodegradation
Toxic
Carcinogenesis
Toxic
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.79
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
6.12
Micronucleos
Toxic
NR-AhR
Safe
NR-AR
Safe
NR-AR-LBD
Safe
NR-Aromatase
Safe
NR-ER
Safe
NR-ER-LBD
Safe
NR-GR
Toxic
NR-PPAR-gamma
Safe
NR-TR
Safe
T. Pyriformis
-3.91
Rat (Acute)
2.39
Rat (Chronic Oral)
2.08
Fathead Minnow
4.36
Respiratory Disease
Safe
Skin Sensitisation
Safe
SR-ARE
Safe
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Toxic

General Properties

Boiling Point
378.95
Hydration Free Energy
-7.97
Log(D) at pH=7.4
1.19
Log(P)
1.46
Log S
-2.9
Log(Vapor Pressure)
-6.81
Melting Point
128.44
pKa Acid
7.91
pKa Basic
3.32
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Type IV / VI secretion system DotU domain-containing protein Q9KN50 Q9KN50_VIBCH Vibrio cholerae serotype O1 3 0.8124
Type IV / VI secretion system DotU domain-containing protein Q9KN50 Q9KN50_VIBCH Vibrio cholerae serotype O1 3 0.8124
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 3 0.7835
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 3 0.7835
Liver carboxylesterase 1 P23141 EST1_HUMAN Homo sapiens 3 0.7775
Liver carboxylesterase 1 P23141 EST1_HUMAN Homo sapiens 3 0.7775
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7470
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7470
Abscisic acid receptor PYR1 O49686 PYR1_ARATH Arabidopsis thaliana 3 0.7429
Abscisic acid receptor PYR1 O49686 PYR1_ARATH Arabidopsis thaliana 3 0.7429
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7317
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7317
Succinate dehydrogenase [ubiquinone] flavoprotein subunit, mitochondrial Q0QF01 SDHA_PIG Sus scrofa 3 0.7176
Succinate dehydrogenase [ubiquinone] flavoprotein subunit, mitochondrial Q0QF01 SDHA_PIG Sus scrofa 3 0.7176
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7028
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7028

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