(4R,5S,6Z,10S)-4,10-dihydroxy-2-methoxy-3-methylidene-6-propylidene-2-azaspiro[4.5]dec-7-ene-1,9-dione

Details

• Internal ID: 631cb4b6-c8df-4f0c-84b2-0d65cf57eac4
• Taxonomy: Organic oxygen compounds > Organooxygen compounds > Carbonyl compounds > Cyclic ketones > Cyclohexenones
• IUPAC Name: (4R,5S,6Z,10S)-4,10-dihydroxy-2-methoxy-3-methylidene-6-propylidene-2-azaspiro[4.5]dec-7-ene-1,9-dione
• SMILES (Canonical): CCC=C1C=CC(=O)C(C12C(C(=C)N(C2=O)OC)O)O
• SMILES (Isomeric): CC/C=C\1/C=CC(=O)[C@H]([C@@]12[C@H](C(=C)N(C2=O)OC)O)O
• InChI: InChI=1S/C14H17NO5/c1-4-5-9-6-7-10(16)12(18)14(9)11(17)8(2)15(20-3)13(14)19/h5-7,11-12,17-18H,2,4H2,1,3H3/b9-5-/t11-,12+,14-/m0/s1
• InChI Key: UEEZHRJFRYRGNC-VXJKQWIASA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₁₄H₁₇NO₅
• Molecular Weight: 279.29 g/mol
• Exact Mass: 279.11067264 g/mol
• Topological Polar Surface Area (TPSA): 87.10 Ų
• XlogP: -0.50
• Atomic LogP (AlogP): 0.09
• H-Bond Acceptor: 5
• H-Bond Donor: 2
• Rotatable Bonds: 2

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.8656	86.56%
Caco-2	-	0.5664	56.64%
Blood Brain Barrier	-	0.6000	60.00%
Human oral bioavailability	+	0.6143	61.43%
Subcellular localzation	Plasma membrane	0.5286	52.86%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8679	86.79%
OATP1B3 inhibitior	+	0.9395	93.95%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	-	0.9750	97.50%
BSEP inhibitior	-	0.8283	82.83%
P-glycoprotein inhibitior	-	0.8956	89.56%
P-glycoprotein substrate	-	0.8183	81.83%
CYP3A4 substrate	+	0.5673	56.73%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8684	86.84%
CYP3A4 inhibition	-	0.9416	94.16%
CYP2C9 inhibition	-	0.7439	74.39%
CYP2C19 inhibition	-	0.7409	74.09%
CYP2D6 inhibition	-	0.8651	86.51%
CYP1A2 inhibition	-	0.7114	71.14%
CYP2C8 inhibition	-	0.7757	77.57%
CYP inhibitory promiscuity	-	0.7476	74.76%
UGT catelyzed	+	0.9000	90.00%
Carcinogenicity (binary)	-	0.7100	71.00%
Carcinogenicity (trinary)	Non-required	0.5034	50.34%
Eye corrosion	-	0.9757	97.57%
Eye irritation	-	0.9233	92.33%
Skin irritation	-	0.7579	75.79%
Skin corrosion	-	0.9206	92.06%
Ames mutagenesis	-	0.6724	67.24%
Human Ether-a-go-go-Related Gene inhibition	-	0.8421	84.21%
Micronuclear	+	0.7500	75.00%
Hepatotoxicity	+	0.5242	52.42%
skin sensitisation	-	0.8281	82.81%
Respiratory toxicity	+	0.6889	68.89%
Reproductive toxicity	+	0.6667	66.67%
Mitochondrial toxicity	+	0.7250	72.50%
Nephrotoxicity	-	0.5817	58.17%
Acute Oral Toxicity (c)	III	0.5484	54.84%
Estrogen receptor binding	+	0.5511	55.11%
Androgen receptor binding	+	0.6310	63.10%
Thyroid receptor binding	+	0.6476	64.76%
Glucocorticoid receptor binding	+	0.6977	69.77%
Aromatase binding	+	0.5248	52.48%
PPAR gamma	-	0.5241	52.41%
Honey bee toxicity	-	0.8280	82.80%
Biodegradation	-	0.8500	85.00%
Crustacea aquatic toxicity	-	0.5300	53.00%
Fish aquatic toxicity	+	0.7233	72.33%

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	95.80%	96.09%
CHEMBL2581	P07339	Cathepsin D	95.55%	98.95%
CHEMBL4040	P28482	MAP kinase ERK2	94.68%	83.82%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	90.64%	91.11%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	89.21%	95.56%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	89.04%	94.45%
CHEMBL1293249	Q13887	Kruppel-like factor 5	88.43%	86.33%
CHEMBL4208	P20618	Proteasome component C5	86.17%	90.00%
CHEMBL253	P34972	Cannabinoid CB2 receptor	82.66%	97.25%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	80.65%	85.14%

Plants that contains it

• Sorbus pallescens

Cross-Links

• PubChem: 10333817
• LOTUS: LTS0057373
• wikiData: Q105270858