13-O-desacetyl-1beta-hydroxy-isoafraglaucolide - Compound Card

13-O-desacetyl-1beta-hydroxy-isoafraglaucolide

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13-O-desacetyl-1beta-hydroxy-isoafraglaucolide

Structure
Zoomed Structure
  • Family: Plantae - Asteraceae
  • Kingdom: Plantae
  • Class: Terpenoid
    • Subclass: Sesquiterpene Lactone
Canonical Smiles OCC1=C2C/C=C(\C)/[C@@H](O)C[C@@H](/C(=C/[C@H]2OC1=O)/C)OC(=O)C
InChI InChI=1S/C17H22O6/c1-9-4-5-12-13(8-18)17(21)23-16(12)6-10(2)15(7-14(9)20)22-11(3)19/h4,6,14-16,18,20H,5,7-8H2,1-3H3/b9-4+,10-6+/t14-,15-,16+/m0/s1
InChIKey UNANNKAWBHGWLX-GEHHHGLQSA-N
Formula C17H22O6
HBA 6
HBD 2
MW 322.36
Rotatable Bonds 2
TPSA 93.06
LogP 1.18
Number Rings 2
Number Aromatic Rings 0
Heavy Atom Count 23
Formal Charge 0
Fraction CSP3 0.53
Exact Mass 322.14
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Artemisia judaica Asteraceae Plantae 205369

Showing of synonyms

  • Khafagy SM, El-din AS, et al. (1988). Glaucolide-like sesquiterpene lactones from Artemisia judaica.. Phytochemistry,1988,27(4),1125-1128. [View]
Pubchem: 14021317
Nmrshiftdb2: 70031245

No compound-protein relationship available.

Structure

SMILES: C1C(=O)OC(C=12)C=CCCCC=CC2

Level: 0

Mol. Weight: 322.36 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.75
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.56
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.98

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
0.4
Plasma Protein Binding
35.07
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
6.23
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-0.81
Biodegradation
Toxic
Carcinogenesis
Toxic
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
-0.06
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
5.46
Micronucleos
Toxic
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
-2.87
Rat (Acute)
2.4
Rat (Chronic Oral)
2.13
Fathead Minnow
4.4
Respiratory Disease
Toxic
Skin Sensitisation
Safe
SR-ARE
Safe
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Toxic

General Properties

Boiling Point
371.74
Hydration Free Energy
-10.71
Log(D) at pH=7.4
0.46
Log(P)
1.18
Log S
-2.16
Log(Vapor Pressure)
-6.77
Melting Point
149.97
pKa Acid
7.96
pKa Basic
4.73
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Liver carboxylesterase 1 P23141 EST1_HUMAN Homo sapiens 3 0.9022
Liver carboxylesterase 1 P23141 EST1_HUMAN Homo sapiens 3 0.9022
Trichothecene 15-O-acetyltransferase TRI3 Q9C1B7 TRI3_FUSSP Fusarium sporotrichioides 3 0.7776
Trichothecene 15-O-acetyltransferase TRI3 Q9C1B7 TRI3_FUSSP Fusarium sporotrichioides 3 0.7776
Succinate dehydrogenase [ubiquinone] flavoprotein subunit, mitochondrial Q0QF01 SDHA_PIG Sus scrofa 3 0.7438
Succinate dehydrogenase [ubiquinone] flavoprotein subunit, mitochondrial Q0QF01 SDHA_PIG Sus scrofa 3 0.7438
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7366
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7366
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.7346
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.7346
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 2 0.7232
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 2 0.7232
Cysteine synthase P45040 CYSK_HAEIN Haemophilus influenzae 3 0.7184
Cysteine synthase P45040 CYSK_HAEIN Haemophilus influenzae 3 0.7184
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.7034
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.7034

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