Coibacin B

Details

• Internal ID: d30aaf46-87df-4290-a870-a320a78b0f0e
• Taxonomy: Organoheterocyclic compounds > Pyrans > Pyranones and derivatives > Dihydropyranones
• IUPAC Name: (2S)-2-[(1E,3E,7E)-8-[(1S,2S)-2-methylcyclopropyl]octa-1,3,7-trienyl]-2,3-dihydropyran-6-one
• SMILES (Canonical): CC1CC1C=CCCC=CC=CC2CC=CC(=O)O2
• SMILES (Isomeric): C[C@H]1C[C@@H]1/C=C/CC/C=C/C=C/[C@@H]2CC=CC(=O)O2
• InChI: InChI=1S/C17H22O2/c1-14-13-15(14)9-6-4-2-3-5-7-10-16-11-8-12-17(18)19-16/h3,5-10,12,14-16H,2,4,11,13H2,1H3/b5-3+,9-6+,10-7+/t14-,15-,16+/m0/s1
• InChI Key: PSXMSFFZXPEIJP-KLCVJRGZSA-N
• Popularity: 2 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₇H₂₂O₂
• Molecular Weight: 258.35 g/mol
• Exact Mass: 258.161979940 g/mol
• Topological Polar Surface Area (TPSA): 26.30 Ų
• XlogP: 4.30
• Atomic LogP (AlogP): 3.96
• H-Bond Acceptor: 2
• H-Bond Donor: 0
• Rotatable Bonds: 6

Synonyms

• (2S)-2-((1E,3E,7E)-8-((1S,2S)-2-methylcyclopropyl)octa-1,3,7-trienyl)-2,3-dihydropyran-6-one
• (2S)-2-[(1E,3E,7E)-8-[(1S,2S)-2-methylcyclopropyl]octa-1,3,7-trienyl]-2,3-dihydropyran-6-one
• RefChem:127423
• (2R)-2-((1E,3E,7E)-8-((1S,2S)-2-methylcyclopropyl)octa-1,3,7-trienyl)-2,3-dihydropyran-6-one
• (2S)-2-((1E,3E,7E)-8-((1R,2S)-2-methylcyclopropyl)octa-1,3,7-trienyl)-2,3-dihydropyran-6-one
• CHEBI:221533

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9938	99.38%
Caco-2	+	0.7758	77.58%
Blood Brain Barrier	+	0.7500	75.00%
Human oral bioavailability	-	0.5429	54.29%
Subcellular localzation	Mitochondria	0.4539	45.39%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8914	89.14%
OATP1B3 inhibitior	+	0.9541	95.41%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	-	0.7750	77.50%
BSEP inhibitior	-	0.5744	57.44%
P-glycoprotein inhibitior	-	0.8437	84.37%
P-glycoprotein substrate	-	0.7223	72.23%
CYP3A4 substrate	+	0.5413	54.13%
CYP2C9 substrate	-	0.6093	60.93%
CYP2D6 substrate	-	0.9072	90.72%
CYP3A4 inhibition	-	0.8772	87.72%
CYP2C9 inhibition	-	0.9447	94.47%
CYP2C19 inhibition	-	0.7552	75.52%
CYP2D6 inhibition	-	0.9508	95.08%
CYP1A2 inhibition	-	0.6802	68.02%
CYP2C8 inhibition	-	0.8723	87.23%
CYP inhibitory promiscuity	-	0.9055	90.55%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.8728	87.28%
Carcinogenicity (trinary)	Non-required	0.6350	63.50%
Eye corrosion	-	0.6771	67.71%
Eye irritation	-	0.8220	82.20%
Skin irritation	+	0.7323	73.23%
Skin corrosion	-	0.9015	90.15%
Ames mutagenesis	-	0.6100	61.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4501	45.01%
Micronuclear	-	0.8200	82.00%
Hepatotoxicity	+	0.7461	74.61%
skin sensitisation	+	0.5834	58.34%
Respiratory toxicity	+	0.5444	54.44%
Reproductive toxicity	-	0.7889	78.89%
Mitochondrial toxicity	-	0.8250	82.50%
Nephrotoxicity	-	0.6387	63.87%
Acute Oral Toxicity (c)	III	0.6437	64.37%
Estrogen receptor binding	-	0.6120	61.20%
Androgen receptor binding	-	0.6822	68.22%
Thyroid receptor binding	-	0.5065	50.65%
Glucocorticoid receptor binding	-	0.5126	51.26%
Aromatase binding	-	0.5276	52.76%
PPAR gamma	-	0.5518	55.18%
Honey bee toxicity	-	0.8732	87.32%
Biodegradation	-	0.7000	70.00%
Crustacea aquatic toxicity	+	0.6000	60.00%
Fish aquatic toxicity	+	0.7672	76.72%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	90.85%	95.56%
CHEMBL5697	Q9GZT9	Egl nine homolog 1	87.08%	93.40%
CHEMBL3137262	O60341	LSD1/CoREST complex	85.52%	97.09%
CHEMBL1293267	Q9HC97	G-protein coupled receptor 35	84.68%	89.34%
CHEMBL2581	P07339	Cathepsin D	81.68%	98.95%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	81.23%	96.09%

Plants that contains it

There are no matching plants.

Cross-Links

• PubChem: 60203969
• LOTUS: LTS0171456
• wikiData: Q105214455