Xanthoxin

Details

• Internal ID: acf5dcb5-4392-4d78-adc4-14f3a227c16c
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Sesquiterpenoids
• IUPAC Name: (2Z,4E)-5-[(1S,4S,6R)-4-hydroxy-2,2,6-trimethyl-7-oxabicyclo[4.1.0]heptan-1-yl]-3-methylpenta-2,4-dienal
• SMILES (Canonical): CC(=CC=O)C=CC12C(CC(CC1(O2)C)O)(C)C
• SMILES (Isomeric): C/C(=C/C=O)/C=C/[C@]12[C@](O1)(C[C@H](CC2(C)C)O)C
• InChI: InChI=1S/C15H22O3/c1-11(6-8-16)5-7-15-13(2,3)9-12(17)10-14(15,4)18-15/h5-8,12,17H,9-10H2,1-4H3/b7-5+,11-6-/t12-,14+,15-/m0/s1
• InChI Key: ZTALKMXOHWQNIA-TVBSHJCBSA-N
• Popularity: 18 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₅H₂₂O₃
• Molecular Weight: 250.33 g/mol
• Exact Mass: 250.15689456 g/mol
• Topological Polar Surface Area (TPSA): 49.80 Ų
• XlogP: 2.00
• Atomic LogP (AlogP): 2.40
• H-Bond Acceptor: 3
• H-Bond Donor: 1
• Rotatable Bonds: 3

Synonyms

• 2-cis,4-trans-Xanthoxin
• 8066-07-7
• (2Z,4E)-5-[(1S,4S,6R)-4-hydroxy-2,2,6-trimethyl-7-oxabicyclo[4.1.0]hept-1-yl]-3-methylpenta-2,4-dienal
• SCHEMBL98130
• CHEBI:32304
• DTXSID601035303
• (1S-(1alpha(2Z,4E),4alpha,6alpha))-5-(4-Hydroxy-2,2,6-trimethyl-7-oxabicyclo(4.1.0)hept-1-yl)-3-methylpenta-2,4-dienal
• [1s-[1Alpha(2Z,4E),4alpha,6alpha]]-5-(4-hydroxy-2,2,6-trimethyl-7-oxabicyclo[4.1.0]hept-1-yl)-3-methylpenta-2,4-dienal
• EINECS 232-513-2
• Q5933737
• (2Z,4E)-5-[(1S,4S,6R)-4-hydroxy-2,2,6-trimethyl-7-oxabicyclo[4.1.0]heptan-1-yl]-3-methylpenta-2,4-dienal
• [1S-[1 alpha(E,E),4 alpha,6 alpha]]-5-(4-Hydroxy-2,2,6-trimethyl-7-oxabicyclo[4.1.0]hept-1-yl]-3-methyl-2,4-pentadienal mixt. with [1S-[1 alpha(Z,E),4 alpha,6 alpha]]-5-(4-Hydroxy-2,2,6 trimethyl-7-oxabicyclo[4.1.0]hept-1-yl]-3-methyl-2,4-pentadienal
• 2,4-Pentadienal, 5-[(1S,4S,6R)-4-hydroxy-2,2,6-trimethyl-7-oxabicyclo[4.1.0]hept-1-yl]-3-methyl-, (2Z,4E)-

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9918	99.18%
Caco-2	+	0.8424	84.24%
Blood Brain Barrier	+	0.6250	62.50%
Human oral bioavailability	+	0.5286	52.86%
Subcellular localzation	Mitochondria	0.5598	55.98%
OATP2B1 inhibitior	-	0.8591	85.91%
OATP1B1 inhibitior	+	0.9001	90.01%
OATP1B3 inhibitior	+	0.9735	97.35%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.8250	82.50%
BSEP inhibitior	-	0.5709	57.09%
P-glycoprotein inhibitior	-	0.9625	96.25%
P-glycoprotein substrate	-	0.8494	84.94%
CYP3A4 substrate	+	0.5992	59.92%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8576	85.76%
CYP3A4 inhibition	-	0.8744	87.44%
CYP2C9 inhibition	-	0.8143	81.43%
CYP2C19 inhibition	-	0.6725	67.25%
CYP2D6 inhibition	-	0.9501	95.01%
CYP1A2 inhibition	-	0.8162	81.62%
CYP2C8 inhibition	-	0.9188	91.88%
CYP inhibitory promiscuity	-	0.9334	93.34%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.8213	82.13%
Carcinogenicity (trinary)	Non-required	0.5406	54.06%
Eye corrosion	-	0.9730	97.30%
Eye irritation	-	0.8348	83.48%
Skin irritation	-	0.5199	51.99%
Skin corrosion	-	0.9293	92.93%
Ames mutagenesis	+	0.5200	52.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.7255	72.55%
Micronuclear	-	0.6600	66.00%
Hepatotoxicity	-	0.5783	57.83%
skin sensitisation	+	0.6064	60.64%
Respiratory toxicity	-	0.5556	55.56%
Reproductive toxicity	-	0.5000	50.00%
Mitochondrial toxicity	+	0.5375	53.75%
Nephrotoxicity	+	0.5422	54.22%
Acute Oral Toxicity (c)	III	0.5413	54.13%
Estrogen receptor binding	+	0.6471	64.71%
Androgen receptor binding	+	0.5590	55.90%
Thyroid receptor binding	+	0.6244	62.44%
Glucocorticoid receptor binding	+	0.5653	56.53%
Aromatase binding	+	0.5198	51.98%
PPAR gamma	-	0.5786	57.86%
Honey bee toxicity	-	0.7962	79.62%
Biodegradation	-	0.7500	75.00%
Crustacea aquatic toxicity	-	0.6300	63.00%
Fish aquatic toxicity	+	0.8510	85.10%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	95.23%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	91.47%	91.11%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	86.48%	95.56%
CHEMBL1806	P11388	DNA topoisomerase II alpha	84.25%	89.00%
CHEMBL1994	P08235	Mineralocorticoid receptor	82.23%	100.00%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	80.62%	96.77%

Plants that contains it

• Acilepidopsis echitifolia
• Acmella alba
• Arnica chamissonis
• Breynia quadrangularis
• Eucalyptus exserta
• Euphorbia bivonae
• Inga paterno
• Phaseolus vulgaris
• Phegopteris subaurita
• Populus tremula
• Pueraria montana var. lobata

Cross-Links

• PubChem: 5282222
• NPASS: NPC6440
• LOTUS: LTS0200970
• wikiData: Q5933737