Dehydrobruceantinol

Details

• Internal ID: a666cd6f-fc70-4960-8120-86e04e622e8a
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Quassinoids
• IUPAC Name: methyl (1R,2S,3R,6R,13S,14R,15R,16S,17S)-3-[(E)-4-acetyloxy-3,4-dimethylpent-2-enoyl]oxy-11,15,16-trihydroxy-9,13-dimethyl-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)C=C(C)C(C)(C)OC(=O)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)/C=C(\C)/C(C)(C)OC(=O)C)([C@H]([C@@H]([C@@H]5[C@]2(C=C(C1=O)O)C)O)O)C(=O)OC
• InChI: InChI=1S/C30H36O13/c1-12(27(4,5)43-14(3)31)8-18(33)42-21-23-29-11-40-30(23,26(38)39-7)24(36)20(35)22(29)28(6)10-16(32)19(34)13(2)15(28)9-17(29)41-25(21)37/h8,10,17,20-24,32,35-36H,9,11H2,1-7H3/b12-8+/t17-,20-,21-,22-,23-,24+,28+,29-,30+/m1/s1
• InChI Key: MJOFLSVJDZIFKV-UUTDASJCSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₃₀H₃₆O₁₃
• Molecular Weight: 604.60 g/mol
• Exact Mass: 604.21559120 g/mol
• Topological Polar Surface Area (TPSA): 192.00 Ų
• XlogP: 1.40
• Atomic LogP (AlogP): 0.76
• H-Bond Acceptor: 13
• H-Bond Donor: 3
• Rotatable Bonds: 5

Synonyms

• Dehydrobruceantinol
• 99132-99-7
• NSC330518
• AKOS040761589
• NSC-330518
• HY-135421
• CS-0112731
• methyl (1R,2S,3R,6R,13S,14R,15R,16S,17S)-3-[(E)-4-acetyloxy-3,4-dimethylpent-2-enoyl]oxy-11,15,16-trihydroxy-9,13-dimethyl-4,10-dioxo-5,18-dioxapentacyclo[12.5.0.01,6.02,17.08,13]nonadeca-8,11-diene-17-carboxylate
• Picrasa-1, 15-[[4-(acetyloxy)-3,4-dimethyl-1-oxo-2-pentenyl]oxy]-13,20-epoxy-/2,11,12-trihydroxy-3,16-dioxo-, methyl ester, [11.beta.,12.alpha.,15.beta.(E)]-

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9330	93.30%
Caco-2	-	0.8203	82.03%
Blood Brain Barrier	-	0.6250	62.50%
Human oral bioavailability	-	0.5857	58.57%
Subcellular localzation	Mitochondria	0.8328	83.28%
OATP2B1 inhibitior	-	0.5716	57.16%
OATP1B1 inhibitior	+	0.8439	84.39%
OATP1B3 inhibitior	+	0.9589	95.89%
MATE1 inhibitior	-	0.9000	90.00%
OCT2 inhibitior	-	0.8500	85.00%
BSEP inhibitior	+	0.9376	93.76%
P-glycoprotein inhibitior	+	0.7931	79.31%
P-glycoprotein substrate	+	0.8044	80.44%
CYP3A4 substrate	+	0.7182	71.82%
CYP2C9 substrate	-	0.8217	82.17%
CYP2D6 substrate	-	0.8917	89.17%
CYP3A4 inhibition	-	0.8001	80.01%
CYP2C9 inhibition	-	0.8448	84.48%
CYP2C19 inhibition	-	0.8480	84.80%
CYP2D6 inhibition	-	0.9159	91.59%
CYP1A2 inhibition	-	0.8211	82.11%
CYP2C8 inhibition	+	0.5891	58.91%
CYP inhibitory promiscuity	-	0.8866	88.66%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9400	94.00%
Carcinogenicity (trinary)	Non-required	0.4433	44.33%
Eye corrosion	-	0.9858	98.58%
Eye irritation	-	0.9111	91.11%
Skin irritation	-	0.6428	64.28%
Skin corrosion	-	0.9229	92.29%
Ames mutagenesis	-	0.6700	67.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5941	59.41%
Micronuclear	-	0.5600	56.00%
Hepatotoxicity	+	0.5806	58.06%
skin sensitisation	-	0.8216	82.16%
Respiratory toxicity	+	0.6889	68.89%
Reproductive toxicity	+	0.9556	95.56%
Mitochondrial toxicity	+	0.7750	77.50%
Nephrotoxicity	+	0.7203	72.03%
Acute Oral Toxicity (c)	III	0.5369	53.69%
Estrogen receptor binding	+	0.7548	75.48%
Androgen receptor binding	+	0.7203	72.03%
Thyroid receptor binding	+	0.5513	55.13%
Glucocorticoid receptor binding	+	0.8160	81.60%
Aromatase binding	+	0.7204	72.04%
PPAR gamma	+	0.7074	70.74%
Honey bee toxicity	-	0.6378	63.78%
Biodegradation	-	0.7250	72.50%
Crustacea aquatic toxicity	+	0.5500	55.00%
Fish aquatic toxicity	+	0.9650	96.50%

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	99.21%	91.11%
CHEMBL2581	P07339	Cathepsin D	96.07%	98.95%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	95.38%	85.14%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	94.88%	95.56%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	92.74%	96.00%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	92.55%	96.09%
CHEMBL5966	P55899	IgG receptor FcRn large subunit p51	92.21%	90.93%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	91.81%	94.45%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	88.20%	99.23%
CHEMBL3145	P42338	PI3-kinase p110-beta subunit	87.21%	98.75%
CHEMBL1806	P11388	DNA topoisomerase II alpha	86.86%	89.00%
CHEMBL1907600	Q00535	Cyclin-dependent kinase 5/CDK5 activator 1	86.04%	93.03%
CHEMBL5028	O14672	ADAM10	86.03%	97.50%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	85.42%	94.33%
CHEMBL1994	P08235	Mineralocorticoid receptor	85.34%	100.00%
CHEMBL5608	Q16288	NT-3 growth factor receptor	85.29%	95.89%
CHEMBL3267	P48736	PI3-kinase p110-gamma subunit	84.98%	95.71%
CHEMBL1293249	Q13887	Kruppel-like factor 5	84.37%	86.33%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	84.18%	97.14%
CHEMBL4005	P42336	PI3-kinase p110-alpha subunit	83.52%	97.47%
CHEMBL3922	P50579	Methionine aminopeptidase 2	82.96%	97.28%
CHEMBL1907605	P24864	Cyclin-dependent kinase 2/cyclin E1	82.26%	92.88%
CHEMBL5163	Q9NY46	Sodium channel protein type III alpha subunit	81.85%	96.90%
CHEMBL1293267	Q9HC97	G-protein coupled receptor 35	81.74%	89.34%
CHEMBL340	P08684	Cytochrome P450 3A4	81.65%	91.19%
CHEMBL3713062	P10646	Tissue factor pathway inhibitor	81.49%	97.33%
CHEMBL3401	O75469	Pregnane X receptor	81.12%	94.73%

Plants that contains it

• Asplenium normale
• Brucea antidysenterica
• 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: 54604632
• NPASS: NPC190094
• LOTUS: LTS0244764
• wikiData: Q105165551