1,2-Dihydrobruceajavanin A

Details

• Internal ID: b44e27d7-c4e3-4939-a6b1-4d259cb925a9
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Triterpenoids > Limonoids
• IUPAC Name: [(5R,7R,8R,9R,10R,13S,17S)-17-[(2R,3S,5R)-2-acetyloxy-5-[(2S)-3,3-dimethyloxiran-2-yl]oxolan-3-yl]-4,4,8,10,13-pentamethyl-3-oxo-1,2,5,6,7,9,11,12,16,17-decahydrocyclopenta[a]phenanthren-7-yl] acetate
• SMILES (Canonical): CC(=O)OC1CC2C(C(=O)CCC2(C3C1(C4=CCC(C4(CC3)C)C5CC(OC5OC(=O)C)C6C(O6)(C)C)C)C)(C)C
• SMILES (Isomeric): CC(=O)O[C@@H]1C[C@@H]2[C@](CCC(=O)C2(C)C)([C@@H]3[C@@]1(C4=CC[C@H]([C@@]4(CC3)C)[C@@H]5C[C@@H](O[C@@H]5OC(=O)C)[C@H]6C(O6)(C)C)C)C
• InChI: InChI=1S/C34H50O7/c1-18(35)38-27-17-25-30(3,4)26(37)13-15-33(25,8)24-12-14-32(7)21(10-11-23(32)34(24,27)9)20-16-22(28-31(5,6)41-28)40-29(20)39-19(2)36/h11,20-22,24-25,27-29H,10,12-17H2,1-9H3/t20-,21-,22+,24+,25-,27+,28-,29-,32-,33+,34-/m0/s1
• InChI Key: VXQBJZLNZQLKCS-DAMXAWHRSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₃₄H₅₀O₇
• Molecular Weight: 570.80 g/mol
• Exact Mass: 570.35565393 g/mol
• Topological Polar Surface Area (TPSA): 91.40 Ų
• XlogP: 5.60
• Atomic LogP (AlogP): 6.17
• H-Bond Acceptor: 7
• H-Bond Donor: 0
• Rotatable Bonds: 4

Synonyms

• [(5R,7R,8R,9R,10R,13S,17S)-17-[(2R,3S,5R)-2-Acetyloxy-5-[(2S)-3,3-dimethyloxiran-2-yl]oxolan-3-yl]-4,4,8,10,13-pentamethyl-3-oxo-1,2,5,6,7,9,11,12,16,17-decahydrocyclopenta[a]phenanthren-7-yl] acetate

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9934	99.34%
Caco-2	-	0.7442	74.42%
Blood Brain Barrier	+	0.8500	85.00%
Human oral bioavailability	-	0.6429	64.29%
Subcellular localzation	Mitochondria	0.8110	81.10%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8217	82.17%
OATP1B3 inhibitior	+	0.8041	80.41%
MATE1 inhibitior	-	0.8000	80.00%
OCT2 inhibitior	-	0.7500	75.00%
BSEP inhibitior	+	0.8791	87.91%
P-glycoprotein inhibitior	+	0.8241	82.41%
P-glycoprotein substrate	-	0.6425	64.25%
CYP3A4 substrate	+	0.7305	73.05%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8636	86.36%
CYP3A4 inhibition	-	0.5425	54.25%
CYP2C9 inhibition	-	0.7603	76.03%
CYP2C19 inhibition	-	0.8218	82.18%
CYP2D6 inhibition	-	0.9418	94.18%
CYP1A2 inhibition	-	0.7550	75.50%
CYP2C8 inhibition	+	0.7042	70.42%
CYP inhibitory promiscuity	-	0.8079	80.79%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.9400	94.00%
Carcinogenicity (trinary)	Non-required	0.4503	45.03%
Eye corrosion	-	0.9867	98.67%
Eye irritation	-	0.9181	91.81%
Skin irritation	-	0.5885	58.85%
Skin corrosion	-	0.8996	89.96%
Ames mutagenesis	-	0.6800	68.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7041	70.41%
Micronuclear	-	0.5000	50.00%
Hepatotoxicity	-	0.6750	67.50%
skin sensitisation	-	0.7976	79.76%
Respiratory toxicity	+	0.8667	86.67%
Reproductive toxicity	+	0.9000	90.00%
Mitochondrial toxicity	+	0.8500	85.00%
Nephrotoxicity	+	0.7034	70.34%
Acute Oral Toxicity (c)	III	0.4210	42.10%
Estrogen receptor binding	+	0.7622	76.22%
Androgen receptor binding	+	0.7041	70.41%
Thyroid receptor binding	+	0.5530	55.30%
Glucocorticoid receptor binding	+	0.7381	73.81%
Aromatase binding	+	0.7032	70.32%
PPAR gamma	+	0.7439	74.39%
Honey bee toxicity	-	0.6914	69.14%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	-	0.5200	52.00%
Fish aquatic toxicity	+	0.9969	99.69%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL4040	P28482	MAP kinase ERK2	96.49%	83.82%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	95.97%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	93.84%	91.11%
CHEMBL1994	P08235	Mineralocorticoid receptor	91.50%	100.00%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	89.56%	99.23%
CHEMBL3137262	O60341	LSD1/CoREST complex	89.50%	97.09%
CHEMBL340	P08684	Cytochrome P450 3A4	88.77%	91.19%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	88.42%	94.45%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	88.37%	95.56%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	86.87%	94.00%
CHEMBL3351	Q13085	Acetyl-CoA carboxylase 1	86.72%	93.04%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	85.36%	85.14%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	83.84%	82.69%
CHEMBL5028	O14672	ADAM10	83.59%	97.50%
CHEMBL5255	O00206	Toll-like receptor 4	83.02%	92.50%
CHEMBL4681	P42330	Aldo-keto-reductase family 1 member C3	82.10%	89.05%
CHEMBL259	P32245	Melanocortin receptor 4	81.90%	95.38%
CHEMBL1937	Q92769	Histone deacetylase 2	80.51%	94.75%

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: 10076750
• NPASS: NPC179393
• LOTUS: LTS0228196
• wikiData: Q105298685