Methyl (9Z)-8'-oxo-6,8'-diapo-6-carotenoate

Details

• Internal ID: d360833f-6463-4341-bf1a-8e85a5af53a2
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Diterpenoids > Acyclic diterpenoids
• IUPAC Name: methyl (2E,4Z,6E,8E,10E,12E,14E,16E)-4,8,13,17-tetramethyl-18-oxooctadeca-2,4,6,8,10,12,14,16-octaenoate
• SMILES (Canonical): CC(=CC=CC=C(C)C=CC=C(C)C=O)C=CC=C(C)C=CC(=O)OC
• SMILES (Isomeric): C/C(=C\C=C\C=C(/C)\C=C\C=C(/C)\C=O)/C=C/C=C(/C)\C=C\C(=O)OC
• InChI: InChI=1S/C23H28O3/c1-19(12-8-14-21(3)16-17-23(25)26-5)10-6-7-11-20(2)13-9-15-22(4)18-24/h6-18H,1-5H3/b7-6+,12-8+,13-9+,17-16+,19-10+,20-11+,21-14-,22-15+
• InChI Key: JMFNGSBVJBPGQR-IWRWKHRWSA-N
• Popularity: 4 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₃H₂₈O₃
• Molecular Weight: 352.50 g/mol
• Exact Mass: 352.20384475 g/mol
• Topological Polar Surface Area (TPSA): 43.40 Ų
• XlogP: 6.60
• Atomic LogP (AlogP): 5.37
• H-Bond Acceptor: 3
• H-Bond Donor: 0
• Rotatable Bonds: 9

Synonyms

• Apo-8'-bixinal
• 101034-51-9
• DTXSID301111192
• Methyl (2E,4Z,6E,8E,10E,12E,14E,16E)-4,8,13,17-tetramethyl-18-oxo-2,4,6,8,10,12,14,16-octadecaoctaenoate
• methyl (2E,4Z,6E,8E,10E,12E,14E,16E)-4,8,13,17-tetramethyl-18-oxooctadeca-2,4,6,8,10,12,14,16-octaenoate

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9892	98.92%
Caco-2	+	0.7485	74.85%
Blood Brain Barrier	+	0.7750	77.50%
Human oral bioavailability	-	0.7000	70.00%
Subcellular localzation	Mitochondria	0.7684	76.84%
OATP2B1 inhibitior	-	0.8580	85.80%
OATP1B1 inhibitior	+	0.8862	88.62%
OATP1B3 inhibitior	+	0.9571	95.71%
MATE1 inhibitior	-	0.8800	88.00%
OCT2 inhibitior	-	0.9750	97.50%
BSEP inhibitior	+	0.9802	98.02%
P-glycoprotein inhibitior	+	0.6576	65.76%
P-glycoprotein substrate	-	0.9168	91.68%
CYP3A4 substrate	-	0.5076	50.76%
CYP2C9 substrate	-	0.5942	59.42%
CYP2D6 substrate	-	0.9046	90.46%
CYP3A4 inhibition	-	0.9517	95.17%
CYP2C9 inhibition	-	0.9267	92.67%
CYP2C19 inhibition	-	0.9309	93.09%
CYP2D6 inhibition	-	0.9537	95.37%
CYP1A2 inhibition	-	0.9288	92.88%
CYP2C8 inhibition	-	0.9390	93.90%
CYP inhibitory promiscuity	-	0.8491	84.91%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	+	0.6481	64.81%
Carcinogenicity (trinary)	Non-required	0.6654	66.54%
Eye corrosion	+	0.8053	80.53%
Eye irritation	-	0.7303	73.03%
Skin irritation	+	0.6075	60.75%
Skin corrosion	-	0.7794	77.94%
Ames mutagenesis	+	0.7100	71.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.8877	88.77%
Micronuclear	-	0.8800	88.00%
Hepatotoxicity	-	0.5819	58.19%
skin sensitisation	+	0.8964	89.64%
Respiratory toxicity	-	0.7444	74.44%
Reproductive toxicity	-	0.9333	93.33%
Mitochondrial toxicity	-	0.8250	82.50%
Nephrotoxicity	+	0.8152	81.52%
Acute Oral Toxicity (c)	III	0.5434	54.34%
Estrogen receptor binding	+	0.9174	91.74%
Androgen receptor binding	-	0.8074	80.74%
Thyroid receptor binding	+	0.6113	61.13%
Glucocorticoid receptor binding	-	0.4681	46.81%
Aromatase binding	+	0.7810	78.10%
PPAR gamma	+	0.5783	57.83%
Honey bee toxicity	-	0.8379	83.79%
Biodegradation	-	0.7500	75.00%
Crustacea aquatic toxicity	-	0.7000	70.00%
Fish aquatic toxicity	+	0.8692	86.92%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL4040	P28482	MAP kinase ERK2	98.67%	83.82%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	88.73%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	85.02%	91.11%
CHEMBL3267	P48736	PI3-kinase p110-gamma subunit	81.87%	95.71%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	80.97%	94.33%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	80.63%	95.50%

Plants that contains it

• Bixa orellana

Cross-Links

• PubChem: 11046403
• LOTUS: LTS0168895
• wikiData: Q76416525