Argentiolide B - Compound Card

Argentiolide B

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Argentiolide B

Structure
Zoomed Structure
  • Family: Plantae - Asteraceae
  • Kingdom: Plantae
  • Class: Terpenoid
    • Subclass: Sesquiterpene Lactone
Canonical Smiles CC(=O)O[C@H]1C/C(=C\CC(=O)[C@H](C[C@@H]2[C@@H]1[C@@H](C)C(=O)O2)C)/C
InChI InChI=1S/C17H24O5/c1-9-5-6-13(19)10(2)8-15-16(11(3)17(20)22-15)14(7-9)21-12(4)18/h5,10-11,14-16H,6-8H2,1-4H3/b9-5-/t10-,11+,14-,15+,16+/m0/s1
InChIKey PRGOXDRZYVDBGK-RPKVYTBNSA-N
Formula C17H24O5
HBA 5
HBD 0
MW 308.37
Rotatable Bonds 1
TPSA 69.67
LogP 2.43
Number Rings 2
Number Aromatic Rings 0
Heavy Atom Count 22
Formal Charge 0
Fraction CSP3 0.71
Exact Mass 308.16
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Artemisia argentea Asteraceae Plantae 669119

Showing of synonyms

  • El-Emary NA, Makboul MA, et al. (1987). Sesquiterpene lactones from Artemisia argentea.. Phytochemistry,1987,26(1),314-315. [View]
Pubchem: 6440538

No compound-protein relationship available.

Structure

SMILES: C1C(=O)OC(C12)CCC(=O)CC=CCC2

Level: 0

Mol. Weight: 308.37 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.65
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.6
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.21

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.54
Plasma Protein Binding
45.87
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
10.94
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-0.22
Biodegradation
Toxic
Carcinogenesis
Toxic
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.59
Liver Injury II
Toxic
hERG Blockers
Toxic
Daphnia Maga
5.14
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
-3.12
Rat (Acute)
2.4
Rat (Chronic Oral)
1.98
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
351.19
Hydration Free Energy
-6.02
Log(D) at pH=7.4
1.03
Log(P)
1.07
Log S
-2.57
Log(Vapor Pressure)
-5.92
Melting Point
113.42
pKa Acid
9.9
pKa Basic
4.36
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 0.8012
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 3 0.8012
Adenylate cyclase type 5 P30803 ADCY5_CANLF Canis lupus familiaris 3 0.8001
Adenylate cyclase type 5 P30803 ADCY5_CANLF Canis lupus familiaris 3 0.8001
Aldo-keto reductase family 1 member C3 P42330 AK1C3_HUMAN Homo sapiens 3 0.7773
Aldo-keto reductase family 1 member C3 P42330 AK1C3_HUMAN Homo sapiens 3 0.7773
Adenylate cyclase type 5 P30803 ADCY5_CANLF Canis lupus familiaris 3 0.7582
Adenylate cyclase type 5 P30803 ADCY5_CANLF Canis lupus familiaris 3 0.7582
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 2 0.7564
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 2 0.7564
ADP-ribosylation factor 1 P84077 ARF1_HUMAN Homo sapiens 2 0.7271
ADP-ribosylation factor 1 P84077 ARF1_HUMAN Homo sapiens 2 0.7271
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.7250
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.7250
Liver carboxylesterase 1 P23141 EST1_HUMAN Homo sapiens 2 0.7245
Liver carboxylesterase 1 P23141 EST1_HUMAN Homo sapiens 2 0.7245
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7178
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7178
Type IV / VI secretion system DotU domain-containing protein Q9KN50 Q9KN50_VIBCH Vibrio cholerae serotype O1 2 0.7145
Type IV / VI secretion system DotU domain-containing protein Q9KN50 Q9KN50_VIBCH Vibrio cholerae serotype O1 2 0.7145
N-alpha-acetyltransferase 50 Q9GZZ1 NAA50_HUMAN Homo sapiens 3 0.7130
N-alpha-acetyltransferase 50 Q9GZZ1 NAA50_HUMAN Homo sapiens 3 0.7130
Cellular retinoic acid-binding protein 2 P29373 RABP2_HUMAN Homo sapiens 2 0.7126
Cellular retinoic acid-binding protein 2 P29373 RABP2_HUMAN Homo sapiens 2 0.7126
ADP-ribosylation factor 1 P84080 ARF1_BOVIN Bos taurus 3 0.7077
ADP-ribosylation factor 1 P84080 ARF1_BOVIN Bos taurus 3 0.7077
Acetylcholinesterase P04058 ACES_TETCF Tetronarce californica 3 0.7026
Acetylcholinesterase P04058 ACES_TETCF Tetronarce californica 3 0.7026
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.7025
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.7025

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