1-[(3aR,7S,8aS)-7-methyl-3-methylidene-2-oxo-2H,3H,3aH,4H,7H,8H,8aH-cyclohepta[b]furan-6-yl]-3-oxobutyl acetate - Compound Card

1-[(3aR,7S,8aS)-7-methyl-3-methylidene-2-oxo-2H,3H,3aH,4H,7H,8H,8aH-cyclohepta[b]furan-6-yl]-3-oxobutyl acetate

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1-[(3aR,7S,8aS)-7-methyl-3-methylidene-2-oxo-2H,3H,3aH,4H,7H,8H,8aH-cyclohepta[b]furan-6-yl]-3-oxobutyl acetate

Structure
Zoomed Structure
  • Family: Plantae - Asteraceae
  • Kingdom: Plantae
  • Class: Terpenoid
    • Subclass: Sesquiterpene Lactone
Canonical Smiles CC(=O)CC(C1=CC[C@H]2[C@H](C[C@@H]1C)OC(=O)C2=C)OC(=O)C
InChI InChI=1S/C17H22O5/c1-9-7-15-14(11(3)17(20)22-15)6-5-13(9)16(8-10(2)18)21-12(4)19/h5,9,14-16H,3,6-8H2,1-2,4H3/t9-,14+,15-,16?/m0/s1
InChIKey DPSCQKGSAHTWSP-LPVYDGHXSA-N
Formula C17H22O5
HBA 5
HBD 0
MW 306.36
Rotatable Bonds 4
TPSA 69.67
LogP 2.35
Number Rings 2
Number Aromatic Rings 0
Heavy Atom Count 22
Formal Charge 0
Fraction CSP3 0.59
Exact Mass 306.15
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Xanthium spinosum Asteraceae Plantae 1053410

Showing of synonyms

  • Abdei-Mogib M, Dawidar AM, et al. (1991). Xanthanolides from Xanthium spinosum. Phytochemistry,1991,30(10),3461-3462. [View]
Pubchem: 442334
Kegg Ligand: C09602
Chebi: 10061
Nmrshiftdb2: 60063646
Bindingdb: 233118
CPRiL: 411878
Structure

SMILES: C=C1C(=O)OC(C12)CCC=CC2

Level: 0

Mol. Weight: 306.36 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.73
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.64
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.29

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.59
Plasma Protein Binding
47.67
Steady State Volume of Distribution
-

Metabolism

Breast Cancer Resistance Protein
Non-Inhibitor
CYP 1A2 Inhibitor
Non-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
0.14
Biodegradation
Toxic
Carcinogenesis
Toxic
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.54
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
5.4
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
0.8
Rat (Acute)
2.57
Rat (Chronic Oral)
1.89
Fathead Minnow
4.12
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
341.72
Hydration Free Energy
-5.68
Log(D) at pH=7.4
1.19
Log(P)
1.27
Log S
-3.01
Log(Vapor Pressure)
-5.97
Melting Point
77.56
pKa Acid
10.23
pKa Basic
4.88
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 3 0.9460
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 3 0.9460
Trichothecene 15-O-acetyltransferase TRI3 Q9C1B7 TRI3_FUSSP Fusarium sporotrichioides 3 0.8627
Trichothecene 15-O-acetyltransferase TRI3 Q9C1B7 TRI3_FUSSP Fusarium sporotrichioides 3 0.8627
Reaction center protein L chain P0C0Y7 RCEH_RHOSH Rhodobacter sphaeroides 3 0.8619
Reaction center protein L chain P0C0Y7 RCEH_RHOSH Rhodobacter sphaeroides 3 0.8619
ADP-ribosylation factor 1 P84080 ARF1_BOVIN Bos taurus 3 0.8452
ADP-ribosylation factor 1 P84080 ARF1_BOVIN Bos taurus 3 0.8452
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 3 0.7408
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 3 0.7408
N-alpha-acetyltransferase 50 Q9GZZ1 NAA50_HUMAN Homo sapiens 3 0.7365
N-alpha-acetyltransferase 50 Q9GZZ1 NAA50_HUMAN Homo sapiens 3 0.7365
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 3 0.7332
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 3 0.7332
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 3 0.7320
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 3 0.7320
Adenylate cyclase type 5 P30803 ADCY5_CANLF Canis lupus familiaris 3 0.7297
Adenylate cyclase type 5 P30803 ADCY5_CANLF Canis lupus familiaris 3 0.7297
Sex hormone-binding globulin P04278 SHBG_HUMAN Homo sapiens 2 0.7215
Sex hormone-binding globulin P04278 SHBG_HUMAN Homo sapiens 2 0.7215
Adenylate cyclase type 5 P30803 ADCY5_CANLF Canis lupus familiaris 3 0.7129
Adenylate cyclase type 5 P30803 ADCY5_CANLF Canis lupus familiaris 3 0.7129
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 2 0.7074
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 2 0.7074
Adenylate cyclase type 5 P30803 ADCY5_CANLF Canis lupus familiaris 3 0.7049
Adenylate cyclase type 5 P30803 ADCY5_CANLF Canis lupus familiaris 3 0.7049

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