Cedrelanolide

Details

• Internal ID: dd6c6dca-4cea-4e27-8a30-49bbe1971533
• Taxonomy: Organoheterocyclic compounds > Benzofurans
• IUPAC Name: methyl (1S,2S,5S,7R)-2-[(3R,3aR,4R,7R,7aR)-4-[(R)-acetyloxy(furan-3-yl)methyl]-7a-formyl-4-methyl-2-oxo-3-propanoyl-3a,5,6,7-tetrahydro-3H-1-benzofuran-7-yl]-2,8,8-trimethyl-3-oxo-6-oxabicyclo[3.2.1]octane-7-carboxylate
• SMILES (Canonical): CCC(=O)C1C2C(CCC(C2(OC1=O)C=O)C3(C4C(OC(C4(C)C)CC3=O)C(=O)OC)C)(C)C(C5=COC=C5)OC(=O)C
• SMILES (Isomeric): CCC(=O)[C@H]1[C@@H]2[C@](CC[C@@H]([C@]2(OC1=O)C=O)[C@@]3([C@H]4[C@@H](O[C@H](C4(C)C)CC3=O)C(=O)OC)C)(C)[C@H](C5=COC=C5)OC(=O)C
• InChI: InChI=1S/C32H40O11/c1-8-18(35)22-24-30(5,26(41-16(2)34)17-10-12-40-14-17)11-9-19(32(24,15-33)43-27(22)37)31(6)20(36)13-21-29(3,4)25(31)23(42-21)28(38)39-7/h10,12,14-15,19,21-26H,8-9,11,13H2,1-7H3/t19-,21+,22+,23-,24-,25+,26+,30-,31+,32-/m1/s1
• InChI Key: UZGWMMOVPDKSHU-CVQXYGNNSA-N
• Popularity: 2 references in papers

Physical and Chemical Properties

• Molecular Formula: C₃₂H₄₀O₁₁
• Molecular Weight: 600.70 g/mol
• Exact Mass: 600.25706209 g/mol
• Topological Polar Surface Area (TPSA): 153.00 Ų
• XlogP: 2.70
• Atomic LogP (AlogP): 3.57
• H-Bond Acceptor: 11
• H-Bond Donor: 0
• Rotatable Bonds: 8

Synonyms

• CHEMBL2269546

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9918	99.18%
Caco-2	-	0.7850	78.50%
Blood Brain Barrier	+	0.8250	82.50%
Human oral bioavailability	-	0.7143	71.43%
Subcellular localzation	Mitochondria	0.6876	68.76%
OATP2B1 inhibitior	-	0.7178	71.78%
OATP1B1 inhibitior	+	0.7442	74.42%
OATP1B3 inhibitior	+	0.8915	89.15%
MATE1 inhibitior	-	0.8400	84.00%
OCT2 inhibitior	-	0.6750	67.50%
BSEP inhibitior	+	0.9786	97.86%
P-glycoprotein inhibitior	+	0.8711	87.11%
P-glycoprotein substrate	+	0.7394	73.94%
CYP3A4 substrate	+	0.7101	71.01%
CYP2C9 substrate	+	0.6122	61.22%
CYP2D6 substrate	-	0.8416	84.16%
CYP3A4 inhibition	+	0.6110	61.10%
CYP2C9 inhibition	-	0.7189	71.89%
CYP2C19 inhibition	-	0.7170	71.70%
CYP2D6 inhibition	-	0.9426	94.26%
CYP1A2 inhibition	-	0.8753	87.53%
CYP2C8 inhibition	+	0.7245	72.45%
CYP inhibitory promiscuity	-	0.7723	77.23%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.9200	92.00%
Carcinogenicity (trinary)	Non-required	0.5366	53.66%
Eye corrosion	-	0.9888	98.88%
Eye irritation	-	0.8836	88.36%
Skin irritation	-	0.7718	77.18%
Skin corrosion	-	0.8905	89.05%
Ames mutagenesis	+	0.5200	52.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7125	71.25%
Micronuclear	-	0.7500	75.00%
Hepatotoxicity	-	0.5250	52.50%
skin sensitisation	-	0.8612	86.12%
Respiratory toxicity	+	0.7111	71.11%
Reproductive toxicity	+	0.7556	75.56%
Mitochondrial toxicity	+	0.5625	56.25%
Nephrotoxicity	-	0.6067	60.67%
Acute Oral Toxicity (c)	III	0.4667	46.67%
Estrogen receptor binding	+	0.8274	82.74%
Androgen receptor binding	+	0.7527	75.27%
Thyroid receptor binding	+	0.6165	61.65%
Glucocorticoid receptor binding	+	0.8188	81.88%
Aromatase binding	+	0.6846	68.46%
PPAR gamma	+	0.7684	76.84%
Honey bee toxicity	-	0.6840	68.40%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	+	0.5600	56.00%
Fish aquatic toxicity	+	0.9879	98.79%

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	98.46%	91.11%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	98.19%	94.45%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	96.08%	96.09%
CHEMBL221	P23219	Cyclooxygenase-1	95.83%	90.17%
CHEMBL4072	P07858	Cathepsin B	95.20%	93.67%
CHEMBL2581	P07339	Cathepsin D	91.89%	98.95%
CHEMBL3137262	O60341	LSD1/CoREST complex	90.20%	97.09%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	88.78%	92.62%
CHEMBL4051	P13569	Cystic fibrosis transmembrane conductance regulator	87.16%	95.71%
CHEMBL3060	Q9Y345	Glycine transporter 2	86.61%	99.17%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	85.91%	85.14%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	84.70%	95.56%
CHEMBL4481	P35228	Nitric oxide synthase, inducible	83.90%	94.80%
CHEMBL255	P29275	Adenosine A2b receptor	83.78%	98.59%
CHEMBL1293249	Q13887	Kruppel-like factor 5	83.06%	86.33%
CHEMBL1806	P11388	DNA topoisomerase II alpha	83.05%	89.00%
CHEMBL340	P08684	Cytochrome P450 3A4	83.00%	91.19%
CHEMBL3401	O75469	Pregnane X receptor	82.98%	94.73%
CHEMBL1937	Q92769	Histone deacetylase 2	82.80%	94.75%
CHEMBL3837	P07711	Cathepsin L	82.20%	96.61%
CHEMBL3524	P56524	Histone deacetylase 4	81.91%	92.97%
CHEMBL3430907	Q96GD4	Aurora kinase B/Inner centromere protein	80.93%	97.50%
CHEMBL3476	O15111	Inhibitor of nuclear factor kappa B kinase alpha subunit	80.68%	95.83%
CHEMBL3830	Q2M2I8	Adaptor-associated kinase	80.00%	83.10%

Plants that contains it

• Cedrela salvadorensis

Cross-Links

• PubChem: 76319625
• LOTUS: LTS0039972
• wikiData: Q105282191