8beta-hydroxy-1-oxo-eudesm-4-en-6alpha,7beta,11betaH-12,6-olide - Compound Card

8beta-hydroxy-1-oxo-eudesm-4-en-6alpha,7beta,11betaH-12,6-olide

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8beta-hydroxy-1-oxo-eudesm-4-en-6alpha,7beta,11betaH-12,6-olide

Structure
Zoomed Structure
  • Family: Plantae - Asteraceae
  • Kingdom: Plantae
  • Class: Terpenoid
    • Subclass: Sesquiterpene Lactone
Canonical Smiles O[C@H]1C[C@@]2(C)C(=O)CCC(=C2[C@@H]2[C@@H]1[C@H](C)C(=O)O2)C
InChI InChI=1S/C15H20O4/c1-7-4-5-10(17)15(3)6-9(16)11-8(2)14(18)19-13(11)12(7)15/h8-9,11,13,16H,4-6H2,1-3H3/t8-,9-,11+,13-,15-/m0/s1
InChIKey BRHPJALTKULBGH-CEBDARMXSA-N
Formula C15H20O4
HBA 4
HBD 1
MW 264.32
Rotatable Bonds 0
TPSA 63.6
LogP 1.61
Number Rings 3
Number Aromatic Rings 0
Heavy Atom Count 19
Formal Charge 0
Fraction CSP3 0.73
Exact Mass 264.14
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Artemisia hugueti Asteraceae Plantae 4219

Showing of synonyms

  • Marco JA, Sanz-Cervera JF, et al. (1994). Sesquiterpene lactones from North African Artemisia species.. Phytochemistry,1994,37(2),477-485. [View]
Pubchem: 12314706
Nmrshiftdb2: 60073057

No compound-protein relationship available.

Structure

SMILES: C1C(=O)OC(C12)C=3C(CC2)C(=O)CCC3

Level: 0

Mol. Weight: 264.32 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.65
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.48
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.45

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.52
Plasma Protein Binding
40.84
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
7.32
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-0.32
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.11
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
4.35
Micronucleos
Safe
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
-1.86
Rat (Acute)
2.53
Rat (Chronic Oral)
1.74
Fathead Minnow
3.85
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
342.41
Hydration Free Energy
-8.18
Log(D) at pH=7.4
0.78
Log(P)
0.59
Log S
-1.99
Log(Vapor Pressure)
-5.85
Melting Point
179.42
pKa Acid
9.04
pKa Basic
4.86
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
11-beta-hydroxysteroid dehydrogenase 1 P28845 DHI1_HUMAN Homo sapiens 3 0.7898
11-beta-hydroxysteroid dehydrogenase 1 P28845 DHI1_HUMAN Homo sapiens 3 0.7898
Type IV / VI secretion system DotU domain-containing protein Q9KN50 Q9KN50_VIBCH Vibrio cholerae serotype O1 2 0.7806
Type IV / VI secretion system DotU domain-containing protein Q9KN50 Q9KN50_VIBCH Vibrio cholerae serotype O1 2 0.7806
Adenylate cyclase type 5 P30803 ADCY5_CANLF Canis lupus familiaris 3 0.7358
Adenylate cyclase type 5 P30803 ADCY5_CANLF Canis lupus familiaris 3 0.7358
Adenylate cyclase type 5 P30803 ADCY5_CANLF Canis lupus familiaris 3 0.7341
Adenylate cyclase type 5 P30803 ADCY5_CANLF Canis lupus familiaris 3 0.7341

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