C-10/C-14-3-isodeoxyarctolide - Compound Card

C-10/C-14-3-isodeoxyarctolide

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C-10/C-14-3-isodeoxyarctolide

Structure
Zoomed Structure
  • Family: Plantae - Asteraceae
  • Kingdom: Plantae
  • Class: Terpenoid
    • Subclass: Sesquiterpene Lactone
Canonical Smiles CC(=O)O[C@@H]1C[C@@H]2[C@@](C1=C)(O)C[C@H]1[C@H](CC2=C)OC(=O)C1=C
InChI InChI=1S/C17H20O5/c1-8-5-15-12(9(2)16(19)22-15)7-17(20)10(3)14(6-13(8)17)21-11(4)18/h12-15,20H,1-3,5-7H2,4H3/t12-,13+,14-,15+,17-/m1/s1
InChIKey WIZNAGDVYMRDHS-LBKYZSNHSA-N
Formula C17H20O5
HBA 5
HBD 1
MW 304.34
Rotatable Bonds 1
TPSA 72.83
LogP 1.67
Number Rings 3
Number Aromatic Rings 0
Heavy Atom Count 22
Formal Charge 0
Fraction CSP3 0.53
Exact Mass 304.13
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Venidium fastuosum Asteraceae Plantae 259861

Showing of synonyms

  • Ali AA, El-Emary NA, et al. (1992). Guaianolides from Venidium fastuosum. Phytochemistry,1992,31(8),2781-2784. [View]
Pubchem: 14285653
Nmrshiftdb2: 70053251

No compound-protein relationship available.

Structure

SMILES: C=C1C(=O)OC(C12)CC(=C)C3C(C2)C(=C)CC3

Level: 0

Mol. Weight: 304.34 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.65
Human Oral Bioavailability 20%
Non-Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.67
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.27

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.52
Plasma Protein Binding
48.01
Steady State Volume of Distribution
-

Metabolism

Breast Cancer Resistance Protein
Non-Inhibitor
CYP 1A2 Inhibitor
Non-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
10.0
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-0.24
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
-0.45
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
4.74
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
0.37
Rat (Acute)
3.35
Rat (Chronic Oral)
1.75
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
332.54
Hydration Free Energy
-6.24
Log(D) at pH=7.4
0.89
Log(P)
1.45
Log S
-2.68
Log(Vapor Pressure)
-6.6
Melting Point
151.73
pKa Acid
6.82
pKa Basic
5.38
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 0.8910
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 3 0.8910
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 3 0.8817
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 3 0.8817
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 3 0.8585
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 3 0.8585
ADP-ribosylation factor 1 P84080 ARF1_BOVIN Bos taurus 3 0.8282
ADP-ribosylation factor 1 P84080 ARF1_BOVIN Bos taurus 3 0.8282
N-alpha-acetyltransferase 50 Q9GZZ1 NAA50_HUMAN Homo sapiens 3 0.7749
N-alpha-acetyltransferase 50 Q9GZZ1 NAA50_HUMAN Homo sapiens 3 0.7749
Sex hormone-binding globulin P04278 SHBG_HUMAN Homo sapiens 2 0.7307
Sex hormone-binding globulin P04278 SHBG_HUMAN Homo sapiens 2 0.7307
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 2 0.7230
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 2 0.7230
Trichothecene 15-O-acetyltransferase TRI3 Q9C1B7 TRI3_FUSSP Fusarium sporotrichioides 3 0.7137
Trichothecene 15-O-acetyltransferase TRI3 Q9C1B7 TRI3_FUSSP Fusarium sporotrichioides 3 0.7137

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