8alpha-acetoxy-2alpha-hydroxy-1alpha,5alpha,6beta,7alpha,11betaH-guaia-3,10(14)-dien-12,6-olide - Compound Card

8alpha-acetoxy-2alpha-hydroxy-1alpha,5alpha,6beta,7alpha,11betaH-guaia-3,10(14)-dien-12,6-olide

Select a section from the left sidebar

8alpha-acetoxy-2alpha-hydroxy-1alpha,5alpha,6beta,7alpha,11betaH-guaia-3,10(14)-dien-12,6-olide

Structure
Zoomed Structure
  • Family: Plantae - Asteraceae
  • Kingdom: Plantae
  • Class: Terpenoid
    • Subclass: Sesquiterpene Lactone
Canonical Smiles CC(=O)O[C@H]1CC(=C)[C@H]2[C@@H]([C@@H]3[C@@H]1[C@H](C)C(=O)O3)C(=C[C@@H]2O)C
InChI InChI=1S/C17H22O5/c1-7-5-11(19)13-8(2)6-12(21-10(4)18)15-9(3)17(20)22-16(15)14(7)13/h5,9,11-16,19H,2,6H2,1,3-4H3/t9-,11-,12-,13+,14-,15+,16+/m0/s1
InChIKey BQUVRDVKRPQXAJ-GZDTUDRRSA-N
Formula C17H22O5
HBA 5
HBD 1
MW 306.36
Rotatable Bonds 1
TPSA 72.83
LogP 1.61
Number Rings 3
Number Aromatic Rings 0
Heavy Atom Count 22
Formal Charge 0
Fraction CSP3 0.65
Exact Mass 306.15
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Artemisia arborescens Asteraceae Plantae 72386

Showing of synonyms

  • Marco JA, Sanz-Cervera JF, et al. (1997). Sesquiterpene lactones and lignans from Artemisia arborescens.. Phytochemistry,1997,44(6),1133-1137. [View]
Pubchem: 100989600

No compound-protein relationship available.

Structure

SMILES: C1=CCC2C(=C)CCC(C3C12)CC(=O)O3

Level: 0

Mol. Weight: 306.36 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.59
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.58
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.38

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.48
Plasma Protein Binding
48.52
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
11.33
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Toxic
Bioconcentration Factor
0.02
Biodegradation
Safe
Carcinogenesis
Toxic
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
-0.53
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
4.98
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
-0.94
Rat (Acute)
3.76
Rat (Chronic Oral)
2.0
Fathead Minnow
3.92
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
359.52
Hydration Free Energy
-7.05
Log(D) at pH=7.4
0.72
Log(P)
1.03
Log S
-2.35
Log(Vapor Pressure)
-6.78
Melting Point
166.22
pKa Acid
8.92
pKa Basic
5.01
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 3 0.9169
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 3 0.9169
Sulfotransferase 2A1 Q06520 ST2A1_HUMAN Homo sapiens 3 0.8869
Sulfotransferase 2A1 Q06520 ST2A1_HUMAN Homo sapiens 3 0.8869
Progesterone receptor P06401 PRGR_HUMAN Homo sapiens 3 0.8489
Progesterone receptor P06401 PRGR_HUMAN Homo sapiens 3 0.8489
Corticosteroid-binding globulin P08185 CBG_HUMAN Homo sapiens 3 0.8271
Corticosteroid-binding globulin P08185 CBG_HUMAN Homo sapiens 3 0.8271
Probable NDP-rhamnosyltransferase Q9ALM8 Q9ALM8_SACSN Saccharopolyspora spinosa 3 0.8212
Probable NDP-rhamnosyltransferase Q9ALM8 Q9ALM8_SACSN Saccharopolyspora spinosa 3 0.8212
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.8156
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.8156
Sulfotransferase 2A1 Q06520 ST2A1_HUMAN Homo sapiens 3 0.7975
Sulfotransferase 2A1 Q06520 ST2A1_HUMAN Homo sapiens 3 0.7975
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7963
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7963
Cytochrome P450 monooxygenase Q5YNS8 Q5YNS8_NOCFA Nocardia farcinica 3 0.7955
Cytochrome P450 monooxygenase Q5YNS8 Q5YNS8_NOCFA Nocardia farcinica 3 0.7955
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7935
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7935
Cytochrome P450 monooxygenase Q5YNS8 Q5YNS8_NOCFA Nocardia farcinica 3 0.7872
Cytochrome P450 monooxygenase Q5YNS8 Q5YNS8_NOCFA Nocardia farcinica 3 0.7872
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.7785
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.7785
Cytochrome P450 monooxygenase Q5YNS8 Q5YNS8_NOCFA Nocardia farcinica 3 0.7582
Cytochrome P450 monooxygenase Q5YNS8 Q5YNS8_NOCFA Nocardia farcinica 3 0.7582
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.7467
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.7467
Progesterone receptor P06401 PRGR_HUMAN Homo sapiens 3 0.7244
Progesterone receptor P06401 PRGR_HUMAN Homo sapiens 3 0.7244
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 2 0.7202
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 2 0.7202
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.7162
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.7162
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7160
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7160
Aromatase P11511 CP19A_HUMAN Homo sapiens 3 0.7129
Aromatase P11511 CP19A_HUMAN Homo sapiens 3 0.7129
Jasmonoyl--L-amino acid synthetase JAR1 Q9SKE2 JAR1_ARATH Arabidopsis thaliana 3 0.7116
Jasmonoyl--L-amino acid synthetase JAR1 Q9SKE2 JAR1_ARATH Arabidopsis thaliana 3 0.7116
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7104
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7104

Download SDF