Dehydrobruceine A

Details

• Internal ID: 1331ad71-6f12-4a25-8a9c-76ed180f1862
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Quassinoids
• IUPAC Name: methyl (1R,2S,3R,6R,13S,14R,15R,16S,17S)-11,15,16-trihydroxy-9,13-dimethyl-3-(3-methylbutanoyloxy)-4,10-dioxo-5,18-dioxapentacyclo[12.5.0.01,6.02,17.08,13]nonadeca-8,11-diene-17-carboxylate
• SMILES (Canonical): CC1=C2CC3C45COC(C4C(C(=O)O3)OC(=O)CC(C)C)(C(C(C5C2(C=C(C1=O)O)C)O)O)C(=O)OC
• SMILES (Isomeric): CC1=C2C[C@@H]3[C@@]45CO[C@@]([C@@H]4[C@H](C(=O)O3)OC(=O)CC(C)C)([C@H]([C@@H]([C@@H]5[C@]2(C=C(C1=O)O)C)O)O)C(=O)OC
• InChI: InChI=1S/C26H32O11/c1-10(2)6-15(28)37-18-20-25-9-35-26(20,23(33)34-5)21(31)17(30)19(25)24(4)8-13(27)16(29)11(3)12(24)7-14(25)36-22(18)32/h8,10,14,17-21,27,30-31H,6-7,9H2,1-5H3/t14-,17-,18-,19-,20-,21+,24+,25-,26+/m1/s1
• InChI Key: RHISAUJYNIABND-IRPUDBTHSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₆H₃₂O₁₁
• Molecular Weight: 520.50 g/mol
• Exact Mass: 520.19446183 g/mol
• Topological Polar Surface Area (TPSA): 166.00 Ų
• XlogP: 1.30
• Atomic LogP (AlogP): 0.52
• H-Bond Acceptor: 11
• H-Bond Donor: 3
• Rotatable Bonds: 4

Synonyms

• 73435-47-9
• HY-N8257
• AKOS040761590
• CS-0142037
• Methyl (1R,2S,3R,6R,13S,14R,15R,16S,17S)-11,15,16-trihydroxy-9,13-dimethyl-3-(3-methylbutanoyloxy)-4,10-dioxo-5,18-dioxapentacyclo[12.5.0.01,6.02,17.08,13]nonadeca-8,11-diene-17-carboxylate

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9364	93.64%
Caco-2	-	0.7702	77.02%
Blood Brain Barrier	-	0.5250	52.50%
Human oral bioavailability	-	0.5857	58.57%
Subcellular localzation	Mitochondria	0.8201	82.01%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8305	83.05%
OATP1B3 inhibitior	+	0.9355	93.55%
MATE1 inhibitior	-	0.9000	90.00%
OCT2 inhibitior	-	0.8250	82.50%
BSEP inhibitior	+	0.7237	72.37%
P-glycoprotein inhibitior	+	0.6888	68.88%
P-glycoprotein substrate	+	0.8418	84.18%
CYP3A4 substrate	+	0.6927	69.27%
CYP2C9 substrate	-	0.8217	82.17%
CYP2D6 substrate	-	0.8917	89.17%
CYP3A4 inhibition	-	0.7694	76.94%
CYP2C9 inhibition	-	0.8082	80.82%
CYP2C19 inhibition	-	0.8490	84.90%
CYP2D6 inhibition	-	0.9300	93.00%
CYP1A2 inhibition	-	0.8347	83.47%
CYP2C8 inhibition	-	0.5828	58.28%
CYP inhibitory promiscuity	-	0.8531	85.31%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.9700	97.00%
Carcinogenicity (trinary)	Non-required	0.4398	43.98%
Eye corrosion	-	0.9873	98.73%
Eye irritation	-	0.9156	91.56%
Skin irritation	-	0.6083	60.83%
Skin corrosion	-	0.9312	93.12%
Ames mutagenesis	-	0.6000	60.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.6625	66.25%
Micronuclear	-	0.6600	66.00%
Hepatotoxicity	+	0.5375	53.75%
skin sensitisation	-	0.8434	84.34%
Respiratory toxicity	+	0.7556	75.56%
Reproductive toxicity	+	0.9556	95.56%
Mitochondrial toxicity	+	0.7625	76.25%
Nephrotoxicity	+	0.7517	75.17%
Acute Oral Toxicity (c)	III	0.5671	56.71%
Estrogen receptor binding	+	0.6766	67.66%
Androgen receptor binding	+	0.6937	69.37%
Thyroid receptor binding	+	0.5164	51.64%
Glucocorticoid receptor binding	+	0.6519	65.19%
Aromatase binding	+	0.6385	63.85%
PPAR gamma	+	0.6468	64.68%
Honey bee toxicity	-	0.7144	71.44%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	-	0.6300	63.00%
Fish aquatic toxicity	+	0.9815	98.15%

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	99.12%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	97.17%	96.09%
CHEMBL2581	P07339	Cathepsin D	97.11%	98.95%
CHEMBL4040	P28482	MAP kinase ERK2	96.53%	83.82%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	96.44%	85.14%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	95.41%	96.00%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	91.54%	94.45%
CHEMBL3130	O00329	PI3-kinase p110-delta subunit	90.67%	96.47%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	90.47%	95.56%
CHEMBL4685	P14902	Indoleamine 2,3-dioxygenase	89.62%	96.38%
CHEMBL3145	P42338	PI3-kinase p110-beta subunit	88.95%	98.75%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	88.66%	94.33%
CHEMBL5966	P55899	IgG receptor FcRn large subunit p51	87.04%	90.93%
CHEMBL1907600	Q00535	Cyclin-dependent kinase 5/CDK5 activator 1	85.72%	93.03%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	85.67%	99.23%
CHEMBL5608	Q16288	NT-3 growth factor receptor	84.13%	95.89%
CHEMBL5028	O14672	ADAM10	84.01%	97.50%
CHEMBL3267	P48736	PI3-kinase p110-gamma subunit	83.33%	95.71%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	82.80%	96.77%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	82.49%	90.71%
CHEMBL2996	Q05655	Protein kinase C delta	82.29%	97.79%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	81.93%	95.89%
CHEMBL340	P08684	Cytochrome P450 3A4	80.98%	91.19%
CHEMBL1806	P11388	DNA topoisomerase II alpha	80.96%	89.00%
CHEMBL2413	P32246	C-C chemokine receptor type 1	80.90%	89.50%
CHEMBL5163	Q9NY46	Sodium channel protein type III alpha subunit	80.47%	96.90%
CHEMBL4051	P13569	Cystic fibrosis transmembrane conductance regulator	80.35%	95.71%
CHEMBL1994	P08235	Mineralocorticoid receptor	80.17%	100.00%

Plants that contains it

• Asplenium normale
• Brucea javanica
• Carpobrotus edulis
• Castanea crenata
• Centrolobium tomentosum
• Ceratophyllum submersum
• Dracocephalum kotschyi
• Lippia carviodora
• Myrica nana
• Psilostrophe cooperi
• Sideritis tragoriganum
• Solanum jamaicense
• Trifolium alexandrinum

Cross-Links

• PubChem: 21125878
• NPASS: NPC24770
• LOTUS: LTS0160627
• wikiData: Q104397414