Proceranolide

Details

• Internal ID: 2be31276-3c3a-4348-936c-14fb44e07d98
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Triterpenoids > Limonoids
• IUPAC Name: methyl 2-[(1R,2S,5R,6R,13S,14R,16S)-6-(furan-3-yl)-14-hydroxy-1,5,15,15-tetramethyl-8,17-dioxo-7-oxatetracyclo[11.3.1.02,11.05,10]heptadec-10-en-16-yl]acetate
• SMILES (Canonical): CC1(C(C2(C3CCC4(C(OC(=O)CC4=C3CC(C1O)C2=O)C5=COC=C5)C)C)CC(=O)OC)C
• SMILES (Isomeric): C[C@@]12CC[C@H]3C(=C1CC(=O)O[C@H]2C4=COC=C4)C[C@H]5[C@H](C([C@@H]([C@@]3(C5=O)C)CC(=O)OC)(C)C)O
• InChI: InChI=1S/C27H34O7/c1-25(2)19(12-20(28)32-5)27(4)17-6-8-26(3)18(15(17)10-16(22(25)30)23(27)31)11-21(29)34-24(26)14-7-9-33-13-14/h7,9,13,16-17,19,22,24,30H,6,8,10-12H2,1-5H3/t16-,17-,19-,22+,24-,26+,27+/m0/s1
• InChI Key: WAIKPAHSFOBDTD-OLJNMEOCSA-N
• Popularity: 4 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₇H₃₄O₇
• Molecular Weight: 470.60 g/mol
• Exact Mass: 470.23045342 g/mol
• Topological Polar Surface Area (TPSA): 103.00 Ų
• XlogP: 2.20
• Atomic LogP (AlogP): 4.16
• H-Bond Acceptor: 7
• H-Bond Donor: 1
• Rotatable Bonds: 3

Synonyms

• CHEBI:68099
• 1915-68-0
• 3Beta-Deacetylfissinolide
• CHEMBL1081393
• WAIKPAHSFOBDTD-OLJNMEOCSA-
• Q27136589
• (4R)-4beta-(3-Furyl)-1,4,4a,5,6,6abeta,7,8,9,10,11,12-dodecahydro-10alpha-hydroxy-4abeta,7,9,9-tetramethyl-2,13-d
• InChI=1/C27H34O7/c1-25(2)19(12-20(28)32-5)27(4)17-6-8-26(3)18(15(17)10-16(22(25)30)23(27)31)11-21(29)34-24(26)14-7-9-33-13-14/h7,9,13,16-17,19,22,24,30H,6,8,10-12H2,1-5H3/t16-,17-,19-,22+,24-,26+,27+/m0/s1
• methyl 2-[(1R,2S,5R,6R,13S,14R,16S)-6-(furan-3-yl)-14-hydroxy-1,5,15,15-tetramethyl-8,17-dioxo-7-oxatetracyclo[11.3.1.02,11.05,10]heptadec-10-en-16-yl]acetate

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9896	98.96%
Caco-2	-	0.6340	63.40%
Blood Brain Barrier	+	0.8250	82.50%
Human oral bioavailability	-	0.5286	52.86%
Subcellular localzation	Mitochondria	0.8698	86.98%
OATP2B1 inhibitior	-	0.8618	86.18%
OATP1B1 inhibitior	-	0.6237	62.37%
OATP1B3 inhibitior	-	0.4694	46.94%
MATE1 inhibitior	-	0.8800	88.00%
OCT2 inhibitior	-	0.7750	77.50%
BSEP inhibitior	+	0.8631	86.31%
P-glycoprotein inhibitior	+	0.6870	68.70%
P-glycoprotein substrate	+	0.5440	54.40%
CYP3A4 substrate	+	0.6841	68.41%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8353	83.53%
CYP3A4 inhibition	+	0.6247	62.47%
CYP2C9 inhibition	-	0.6837	68.37%
CYP2C19 inhibition	-	0.8092	80.92%
CYP2D6 inhibition	-	0.9322	93.22%
CYP1A2 inhibition	-	0.7410	74.10%
CYP2C8 inhibition	+	0.6782	67.82%
CYP inhibitory promiscuity	-	0.6808	68.08%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.9600	96.00%
Carcinogenicity (trinary)	Non-required	0.5303	53.03%
Eye corrosion	-	0.9913	99.13%
Eye irritation	-	0.9207	92.07%
Skin irritation	-	0.6418	64.18%
Skin corrosion	-	0.9315	93.15%
Ames mutagenesis	-	0.7370	73.70%
Human Ether-a-go-go-Related Gene inhibition	+	0.6953	69.53%
Micronuclear	-	0.6400	64.00%
Hepatotoxicity	+	0.6000	60.00%
skin sensitisation	-	0.8584	85.84%
Respiratory toxicity	+	0.8000	80.00%
Reproductive toxicity	+	0.9667	96.67%
Mitochondrial toxicity	+	0.7875	78.75%
Nephrotoxicity	-	0.5945	59.45%
Acute Oral Toxicity (c)	I	0.6675	66.75%
Estrogen receptor binding	+	0.8589	85.89%
Androgen receptor binding	+	0.6958	69.58%
Thyroid receptor binding	+	0.6194	61.94%
Glucocorticoid receptor binding	+	0.8731	87.31%
Aromatase binding	+	0.7523	75.23%
PPAR gamma	+	0.7690	76.90%
Honey bee toxicity	-	0.7914	79.14%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	+	0.6000	60.00%
Fish aquatic toxicity	+	0.9964	99.64%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	97.68%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	97.15%	96.09%
CHEMBL4040	P28482	MAP kinase ERK2	97.02%	83.82%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	94.83%	85.14%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	93.33%	94.45%
CHEMBL3137262	O60341	LSD1/CoREST complex	90.77%	97.09%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	88.73%	94.33%
CHEMBL221	P23219	Cyclooxygenase-1	87.01%	90.17%
CHEMBL1293249	Q13887	Kruppel-like factor 5	86.13%	86.33%
CHEMBL255	P29275	Adenosine A2b receptor	86.00%	98.59%
CHEMBL5608	Q16288	NT-3 growth factor receptor	85.54%	95.89%
CHEMBL1907602	P06493	Cyclin-dependent kinase 1/cyclin B1	85.19%	91.24%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	84.83%	99.23%
CHEMBL1806	P11388	DNA topoisomerase II alpha	84.53%	89.00%
CHEMBL1994	P08235	Mineralocorticoid receptor	84.32%	100.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	83.65%	95.56%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	83.47%	92.62%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	81.63%	94.00%
CHEMBL3038469	P24941	CDK2/Cyclin A	81.17%	91.38%
CHEMBL5028	O14672	ADAM10	81.12%	97.50%
CHEMBL4227	P25090	Lipoxin A4 receptor	80.96%	100.00%
CHEMBL4051	P13569	Cystic fibrosis transmembrane conductance regulator	80.85%	95.71%

Plants that contains it

• Cabralea canjerana
• Cedrela odorata
• Chisocheton ceramicus
• Ekebergia capensis
• Swietenia macrophylla
• Swietenia mahagoni
• Xylocarpus granatum
• Xylocarpus moluccensis

Cross-Links

• PubChem: 23258999
• NPASS: NPC178932
• LOTUS: LTS0167643
• wikiData: Q27136589