1beta,10alpha,2alpha,3alpha-bisepoxy-5beta-hydroxy-8alpha-methacryloyloxy-germacra- 4(15),11(13)-dien-12,6alpha-olide - Compound Card

1beta,10alpha,2alpha,3alpha-bisepoxy-5beta-hydroxy-8alpha-methacryloyloxy-germacra- 4(15),11(13)-dien-12,6alpha-olide

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1beta,10alpha,2alpha,3alpha-bisepoxy-5beta-hydroxy-8alpha-methacryloyloxy-germacra- 4(15),11(13)-dien-12,6alpha-olide

Structure
Zoomed Structure
  • Family: Plantae - Asteraceae
  • Kingdom: Plantae
  • Class: Terpenoid
    • Subclass: Sesquiterpene Lactone
Canonical Smiles C=C1[C@H](O)[C@H]2OC(=O)C(=C)[C@@H]2[C@@H](OC(=O)C(=C)C)C[C@@]2([C@@H]([C@@H]3[C@H]1O3)O2)C
InChI InChI=1S/C19H22O7/c1-7(2)17(21)23-10-6-19(5)16(26-19)15-13(24-15)9(4)12(20)14-11(10)8(3)18(22)25-14/h10-16,20H,1,3-4,6H2,2,5H3/t10-,11+,12-,13-,14-,15-,16+,19+/m0/s1
InChIKey TWHRQBJKTTZFKU-HWEGBDAGSA-N
Formula C19H22O7
HBA 7
HBD 1
MW 362.38
Rotatable Bonds 2
TPSA 97.89
LogP 0.82
Number Rings 4
Number Aromatic Rings 0
Heavy Atom Count 26
Formal Charge 0
Fraction CSP3 0.58
Exact Mass 362.14
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Gutenbergia cordifolia Asteraceae Plantae 1671336

Showing of synonyms

  • Zdero C, Bohlmann F. (1990). Germacranolides from Gutenbergia cordifolia. Phytochemistry,1990,29(8),2706-2708. [View] [PubMed]

No compound-protein relationship available.

Structure

SMILES: C=C1C(=O)OC(CC(=C)C2O3)C1CCC(O4)C4C23

Level: 0

Mol. Weight: 362.38 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-5.15
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.67
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.82

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.19
Plasma Protein Binding
20.71
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
Inhibitor
CYP 3A4 Substrate
Substrate
OATP1B1
Non-Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
14.67
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Toxic
Bioconcentration Factor
0.3
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Toxic
Maximum Tolerated Dose
-0.25
Liver Injury II
Safe
hERG Blockers
Safe
Daphnia Maga
5.26
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
Toxic
NR-TR
Safe
T. Pyriformis
-5.09
Rat (Acute)
5.08
Rat (Chronic Oral)
1.93
Fathead Minnow
3.94
Respiratory Disease
Safe
Skin Sensitisation
Toxic
SR-ARE
Toxic
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Toxic

General Properties

Boiling Point
386.4
Hydration Free Energy
-6.35
Log(D) at pH=7.4
0.59
Log(P)
0.72
Log S
-2.48
Log(Vapor Pressure)
-7.9
Melting Point
124.3
pKa Acid
4.75
pKa Basic
1.41
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 0.8106
Type IV / VI secretion system DotU domain-containing protein Q9KN50 Q9KN50_VIBCH Vibrio cholerae serotype O1 3 0.8106

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