8-epixanthatin - Compound Card

8-epixanthatin

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8-epixanthatin

Structure
Zoomed Structure
  • Family: Plantae - Asteraceae
  • Kingdom: Plantae
  • Class: Terpenoid
    • Subclass: Sesquiterpene Lactone
Canonical Smiles CC(=O)/C=C/C1=CC[C@H]2[C@@H](C[C@@H]1C)OC(=O)C2=C
InChI InChI=1S/C15H18O3/c1-9-8-14-13(11(3)15(17)18-14)7-6-12(9)5-4-10(2)16/h4-6,9,13-14H,3,7-8H2,1-2H3/b5-4+/t9-,13+,14+/m0/s1
InChIKey RBRPTFMVULVGIC-MDKNCZOUSA-N
Formula C15H18O3
HBA 3
HBD 0
MW 246.31
Rotatable Bonds 2
TPSA 43.37
LogP 2.59
Number Rings 2
Number Aromatic Rings 0
Heavy Atom Count 18
Formal Charge 0
Fraction CSP3 0.47
Exact Mass 246.13
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Xanthium pungens Asteraceae Plantae 1979456

Showing of synonyms

  • Ahmed AA, Jakupovic J, et al. (1990). Sesquiterpene lactones from Xanthium pungens. Phytochemistry,1990,29(7),2211-2215. [View]
Pubchem: 11694445
Nmrshiftdb2: 60077463
Bindingdb: 233133
CPRiL: 67953
Structure

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

Level: 0

Mol. Weight: 246.31 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.82
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.33
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.48

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.68
Plasma Protein Binding
59.31
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
Substrate
CYP 2D6 Inhibitor
Non-Inhibitor
CYP 2D6 Substrate
Non-Substrate
CYP 3A4 Inhibitor
Non-Inhibitor
CYP 3A4 Substrate
Substrate
OATP1B1
Non-Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
7.14
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
0.66
Biodegradation
Toxic
Carcinogenesis
Toxic
Crustacean
Toxic
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.2
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
5.35
Micronucleos
Safe
NR-AhR
Safe
NR-AR
Safe
NR-AR-LBD
Toxic
NR-Aromatase
Safe
NR-ER
Safe
NR-ER-LBD
Safe
NR-GR
Toxic
NR-PPAR-gamma
Safe
NR-TR
Safe
T. Pyriformis
2.25
Rat (Acute)
2.21
Rat (Chronic Oral)
1.98
Fathead Minnow
4.24
Respiratory Disease
Toxic
Skin Sensitisation
Toxic
SR-ARE
Toxic
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Toxic

General Properties

Boiling Point
325.64
Hydration Free Energy
-5.05
Log(D) at pH=7.4
2.06
Log(P)
1.43
Log S
-3.64
Log(Vapor Pressure)
-4.9
Melting Point
103.93
pKa Acid
10.18
pKa Basic
5.75
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 0.9072
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 3 0.9072
Reaction center protein L chain P0C0Y7 RCEH_RHOSH Rhodobacter sphaeroides 3 0.8230
Reaction center protein L chain P0C0Y7 RCEH_RHOSH Rhodobacter sphaeroides 3 0.8230
ADP-ribosylation factor 1 P84077 ARF1_HUMAN Homo sapiens 2 0.8214
ADP-ribosylation factor 1 P84077 ARF1_HUMAN Homo sapiens 2 0.8214
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 3 0.8083
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 3 0.8083
Adenylate cyclase type 5 P30803 ADCY5_CANLF Canis lupus familiaris 3 0.7951
Adenylate cyclase type 5 P30803 ADCY5_CANLF Canis lupus familiaris 3 0.7951
N-alpha-acetyltransferase 50 Q9GZZ1 NAA50_HUMAN Homo sapiens 3 0.7722
N-alpha-acetyltransferase 50 Q9GZZ1 NAA50_HUMAN Homo sapiens 3 0.7722
Adenylate cyclase type 5 P30803 ADCY5_CANLF Canis lupus familiaris 3 0.7702
Adenylate cyclase type 5 P30803 ADCY5_CANLF Canis lupus familiaris 3 0.7702
ADP-ribosylation factor 1 P84080 ARF1_BOVIN Bos taurus 3 0.7677
ADP-ribosylation factor 1 P84080 ARF1_BOVIN Bos taurus 3 0.7677
Type IV / VI secretion system DotU domain-containing protein Q9KN50 Q9KN50_VIBCH Vibrio cholerae serotype O1 2 0.7559
Type IV / VI secretion system DotU domain-containing protein Q9KN50 Q9KN50_VIBCH Vibrio cholerae serotype O1 2 0.7559
Liver carboxylesterase 1 P23141 EST1_HUMAN Homo sapiens 2 0.7390
Liver carboxylesterase 1 P23141 EST1_HUMAN Homo sapiens 2 0.7390
Abscisic acid receptor PYL2 O80992 PYL2_ARATH Arabidopsis thaliana 2 0.7360
Abscisic acid receptor PYL2 O80992 PYL2_ARATH Arabidopsis thaliana 2 0.7360
Abscisic acid receptor PYL9 Q84MC7 PYL9_ARATH Arabidopsis thaliana 2 0.7168
Abscisic acid receptor PYL9 Q84MC7 PYL9_ARATH Arabidopsis thaliana 2 0.7168
Sex hormone-binding globulin P04278 SHBG_HUMAN Homo sapiens 2 0.7152
Sex hormone-binding globulin P04278 SHBG_HUMAN Homo sapiens 2 0.7152
N-acetyltransferase domain-containing protein Q9HV14 Q9HV14_PSEAE Pseudomonas aeruginosa 3 0.7145
N-acetyltransferase domain-containing protein Q9HV14 Q9HV14_PSEAE Pseudomonas aeruginosa 3 0.7145
Adenylate cyclase type 5 P30803 ADCY5_CANLF Canis lupus familiaris 3 0.7142
Adenylate cyclase type 5 P30803 ADCY5_CANLF Canis lupus familiaris 3 0.7142
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7081
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7081
Cytochrome P450 Q93H81 Q93H81_STRAX Streptomyces avermitilis 2 0.7034
Cytochrome P450 Q93H81 Q93H81_STRAX Streptomyces avermitilis 2 0.7034

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