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Xanthinosin

Family: Plantae - Asteraceae
Kingdom: Plantae
Class: Terpenoid
- Subclass: Sesquiterpene Lactone

Canonical Smiles	CC(=O)CCC1=CC[C@H]2[C@H](C[C@@H]1C)OC(=O)C2=C
InChI	InChI=1S/C15H20O3/c1-9-8-14-13(11(3)15(17)18-14)7-6-12(9)5-4-10(2)16/h6,9,13-14H,3-5,7-8H2,1-2H3/t9-,13+,14-/m0/s1
InChIKey	AVFIYMSJDDGDBQ-FZZIBODNSA-N
Formula	C₁₅H₂₀O₃
HBA	3
HBD	0
MW	248.32
Rotatable Bonds	3
TPSA	43.37
LogP	2.81
Number Rings	2
Number Aromatic Rings	0
Heavy Atom Count	18
Formal Charge	0
Fraction CSP3	0.6
Exact Mass	248.14
Number of Lipinski Rule Violations	0

#	Species	Family	Kingdom	NCBI Taxonomy ID
1	Pulicaria undulata	Asteraceae	Plantae	119186

Showing of synonyms

Hegazy MEF, Nakamura S, et al. (2015). Rare hydroperoxyl guaianolide sesquiterpenes from Pulicaria undulata. Phytochemistry Letters,2015,12,177-181. [View]

Pubchem: 44453629

Gnps: CCMSLIB00005885182

Zinc: ZINC000029126060

Nmrshiftdb2: 60025618

Chembl: CHEMBL257513

No compound-protein relationship available.

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

Level: 0

Mol. Weight: 248.32 g/mol

Anti-inflammatory

Absorption

Caco-2 (logPapp): -4.83
Human Oral Bioavailability 20%: Bioavailable
Human Intestinal Absorption: Absorbed
Madin-Darby Canine Kidney: -4.53
Human Oral Bioavailability 50%: Bioavailable
P-Glycoprotein Inhibitor: Non-Inhibitor
P-Glycoprotein Substrate: Non-Substrate
Skin Permeability: -2.32

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Penetrable
Fraction Unbound (Human): 0.72
Plasma Protein Binding: 51.87
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: 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: 9.57
Organic Cation Transporter 2: Non-Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Safe
Avian: Safe
Bee: Toxic
Bioconcentration Factor: 0.35
Biodegradation: Toxic
Carcinogenesis: Toxic
Crustacean: Toxic
Liver Injury I (DILI): Safe
Eye Corrosion: Safe
Eye Irritation: Safe
Maximum Tolerated Dose: 0.16
Liver Injury II: Toxic
hERG Blockers: Safe
Daphnia Maga: 4.82
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: 1.36
Rat (Acute): 2.28
Rat (Chronic Oral): 1.84
Fathead Minnow: 4.04
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: 321.82
Hydration Free Energy: -4.7
Log(D) at pH=7.4: 1.86
Log(P): 1.65
Log S: -3.4
Log(Vapor Pressure): -4.57
Melting Point: 64.32
pKa Acid: 10.04
pKa Basic: 4.78

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	0.9638
Pentaerythritol tetranitrate reductase	P71278	P71278_ENTCL	Enterobacter cloacae	3	0.9638
N-alpha-acetyltransferase 50	Q9GZZ1	NAA50_HUMAN	Homo sapiens	3	0.7857
N-alpha-acetyltransferase 50	Q9GZZ1	NAA50_HUMAN	Homo sapiens	3	0.7857
ADP-ribosylation factor 1	P84080	ARF1_BOVIN	Bos taurus	3	0.7786
ADP-ribosylation factor 1	P84080	ARF1_BOVIN	Bos taurus	3	0.7786
Adenylate cyclase type 5	P30803	ADCY5_CANLF	Canis lupus familiaris	3	0.7661
Adenylate cyclase type 5	P30803	ADCY5_CANLF	Canis lupus familiaris	3	0.7661
N-acetyltransferase domain-containing protein	Q9HV14	Q9HV14_PSEAE	Pseudomonas aeruginosa	3	0.7635
N-acetyltransferase domain-containing protein	Q9HV14	Q9HV14_PSEAE	Pseudomonas aeruginosa	3	0.7635
Sex hormone-binding globulin	P04278	SHBG_HUMAN	Homo sapiens	2	0.7603
Sex hormone-binding globulin	P04278	SHBG_HUMAN	Homo sapiens	2	0.7603
Type IV / VI secretion system DotU domain-containing protein	Q9KN50	Q9KN50_VIBCH	Vibrio cholerae serotype O1	2	0.7553
Type IV / VI secretion system DotU domain-containing protein	Q9KN50	Q9KN50_VIBCH	Vibrio cholerae serotype O1	2	0.7553
Ferrochelatase, mitochondrial	P22830	HEMH_HUMAN	Homo sapiens	3	0.7534
Ferrochelatase, mitochondrial	P22830	HEMH_HUMAN	Homo sapiens	3	0.7534
Adenylate cyclase type 5	P30803	ADCY5_CANLF	Canis lupus familiaris	3	0.7466
Adenylate cyclase type 5	P30803	ADCY5_CANLF	Canis lupus familiaris	3	0.7466
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	2	0.7406
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	2	0.7406
Photosynthetic reaction center cytochrome c subunit	P07173	CYCR_BLAVI	Blastochloris viridis	2	0.7399
Photosynthetic reaction center cytochrome c subunit	P07173	CYCR_BLAVI	Blastochloris viridis	2	0.7399
ADP-ribosylation factor 1	P84080	ARF1_BOVIN	Bos taurus	3	0.7339
ADP-ribosylation factor 1	P84080	ARF1_BOVIN	Bos taurus	3	0.7339
Pentaerythritol tetranitrate reductase	P71278	P71278_ENTCL	Enterobacter cloacae	2	0.7319
Pentaerythritol tetranitrate reductase	P71278	P71278_ENTCL	Enterobacter cloacae	2	0.7319
Phosphotriesterase	Q5KZU5	Q5KZU5_GEOKA	Geobacillus kaustophilus	2	0.7311
Phosphotriesterase	Q5KZU5	Q5KZU5_GEOKA	Geobacillus kaustophilus	2	0.7311
ADP-ribosylation factor 1	P84077	ARF1_HUMAN	Homo sapiens	2	0.7277
ADP-ribosylation factor 1	P84077	ARF1_HUMAN	Homo sapiens	2	0.7277
Abscisic acid receptor PYL2	O80992	PYL2_ARATH	Arabidopsis thaliana	2	0.7255
Abscisic acid receptor PYL2	O80992	PYL2_ARATH	Arabidopsis thaliana	2	0.7255
Ferrichrome outer membrane transporter/phage receptor	P06971	FHUA_ECOLI	Escherichia coli	3	0.7224
Ferrichrome outer membrane transporter/phage receptor	P06971	FHUA_ECOLI	Escherichia coli	3	0.7224
Methylketone synthase I	E0YCS2	E0YCS2_SOLHA	Solanum habrochaites	2	0.7211
Methylketone synthase I	E0YCS2	E0YCS2_SOLHA	Solanum habrochaites	2	0.7211
Adenylate cyclase type 5	P30803	ADCY5_CANLF	Canis lupus familiaris	3	0.7204
Adenylate cyclase type 5	P30803	ADCY5_CANLF	Canis lupus familiaris	3	0.7204
Photosynthetic reaction center cytochrome c subunit	P07173	CYCR_BLAVI	Blastochloris viridis	2	0.7183
Photosynthetic reaction center cytochrome c subunit	P07173	CYCR_BLAVI	Blastochloris viridis	2	0.7183
3-alpha-(or 20-beta)-hydroxysteroid dehydrogenase	P19992	HSD_STREX	Streptomyces exfoliatus	2	0.7174
3-alpha-(or 20-beta)-hydroxysteroid dehydrogenase	P19992	HSD_STREX	Streptomyces exfoliatus	2	0.7174
Sulfotransferase 2B1	O00204	ST2B1_HUMAN	Homo sapiens	2	0.7123
Sulfotransferase 2B1	O00204	ST2B1_HUMAN	Homo sapiens	2	0.7123
Liver carboxylesterase 1	P23141	EST1_HUMAN	Homo sapiens	2	0.7098
Liver carboxylesterase 1	P23141	EST1_HUMAN	Homo sapiens	2	0.7098
Transcriptional activator, LuxR/UhpA family of regulators	Q7NQP7	Q7NQP7_CHRVO	Chromobacterium violaceum	2	0.7075
Transcriptional activator, LuxR/UhpA family of regulators	Q7NQP7	Q7NQP7_CHRVO	Chromobacterium violaceum	2	0.7075

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