1alpha-hydoxyeudesm-4(15)-en-5alpha,6beta,11betaH-12,6-olide - Compound Card

1alpha-hydoxyeudesm-4(15)-en-5alpha,6beta,11betaH-12,6-olide

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1alpha-hydoxyeudesm-4(15)-en-5alpha,6beta,11betaH-12,6-olide

Structure
Zoomed Structure
  • Family: Plantae - Asteraceae
  • Kingdom: Plantae
  • Class: Terpenoid
    • Subclass: Sesquiterpene Lactone
Canonical Smiles C=C1CC[C@@H]([C@]2([C@H]1[C@H]1OC(=O)[C@H]([C@@H]1CC2)C)C)O
InChI InChI=1S/C15H22O3/c1-8-4-5-11(16)15(3)7-6-10-9(2)14(17)18-13(10)12(8)15/h9-13,16H,1,4-7H2,2-3H3/t9-,10-,11-,12+,13-,15-/m0/s1
InChIKey JWBPWNWPEVPCMJ-ZDDLAMDLSA-N
Formula C15H22O3
HBA 3
HBD 1
MW 250.34
Rotatable Bonds 0
TPSA 46.53
LogP 2.29
Number Rings 3
Number Aromatic Rings 0
Heavy Atom Count 18
Formal Charge 0
Fraction CSP3 0.8
Exact Mass 250.16
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: 21672184
Nmrshiftdb2: 60072389

No compound-protein relationship available.

Structure

SMILES: C=C1CCCC(CC2)C1C(C23)OC(=O)C3

Level: 0

Mol. Weight: 250.34 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.76
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.37
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.32

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.54
Plasma Protein Binding
46.86
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
13.6
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-0.02
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
-0.67
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
3.72
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
-0.58
Rat (Acute)
2.48
Rat (Chronic Oral)
1.65
Fathead Minnow
3.92
Respiratory Disease
Safe
Skin Sensitisation
Toxic
SR-ARE
Safe
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Toxic

General Properties

Boiling Point
338.54
Hydration Free Energy
-5.93
Log(D) at pH=7.4
1.34
Log(P)
2.39
Log S
-2.32
Log(Vapor Pressure)
-5.05
Melting Point
145.9
pKa Acid
10.45
pKa Basic
6.74
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.8006
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.8006
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7714
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7714
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.7545
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.7545
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7485
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7485
Nuclear receptor subfamily 1 group I member 2 O75469 NR1I2_HUMAN Homo sapiens 3 0.7479
Nuclear receptor subfamily 1 group I member 2 O75469 NR1I2_HUMAN Homo sapiens 3 0.7479
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 2 0.7184
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 2 0.7184
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.7111
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.7111
Beta-1 adrenergic receptor P07700 ADRB1_MELGA Meleagris gallopavo 3 0.7064
Beta-1 adrenergic receptor P07700 ADRB1_MELGA Meleagris gallopavo 3 0.7064

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