Deacetylnimbin

Details

• Internal ID: b8a0c8f1-1436-42e6-a2ef-2b2be58ce048
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Triterpenoids > Limonoids
• IUPAC Name: methyl (1S,2R,3R,4R,8R,9S,10R,13R,15R)-13-(furan-3-yl)-2-hydroxy-9-(2-methoxy-2-oxoethyl)-4,8,10,12-tetramethyl-7-oxo-16-oxatetracyclo[8.6.0.03,8.011,15]hexadeca-5,11-diene-4-carboxylate
• SMILES (Canonical): CC1=C2C(CC1C3=COC=C3)OC4C2(C(C5(C(C4O)C(C=CC5=O)(C)C(=O)OC)C)CC(=O)OC)C
• SMILES (Isomeric): CC1=C2[C@@H](C[C@H]1C3=COC=C3)O[C@H]4[C@@]2([C@@H]([C@@]5([C@@H]([C@H]4O)[C@](C=CC5=O)(C)C(=O)OC)C)CC(=O)OC)C
• InChI: InChI=1S/C28H34O8/c1-14-16(15-8-10-35-13-15)11-17-21(14)28(4)18(12-20(30)33-5)27(3)19(29)7-9-26(2,25(32)34-6)23(27)22(31)24(28)36-17/h7-10,13,16-18,22-24,31H,11-12H2,1-6H3/t16-,17-,18-,22-,23+,24-,26-,27+,28-/m1/s1
• InChI Key: CTBHKOAPXBDFPX-PQYHCQQJSA-N
• Popularity: 18 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₈H₃₄O₈
• Molecular Weight: 498.60 g/mol
• Exact Mass: 498.22536804 g/mol
• Topological Polar Surface Area (TPSA): 112.00 Ų
• XlogP: 1.70
• Atomic LogP (AlogP): 3.35
• H-Bond Acceptor: 8
• H-Bond Donor: 1
• Rotatable Bonds: 4

Synonyms

• 6-Deacetylnimbin
• Desacetylnimbin
• 6-Desacetylnimbin
• 18609-16-0
• nimbic acid dimethyl ester
• CHEBI:67305
• Nimbic acid, dimethyl ester
• CHEMBL1774398
• HY-N3694
• AKOS032948232
• CS-0024075
• Q27135761
• methyl (2R,3aR,4aS,5R,5aR,6R,9aR,10S,10aR)-2-(furan-3-yl)-5-hydroxy-10-(2-methoxy-2-oxoethyl)-1,6,9a,10a-tetramethyl-9-oxo-3,3a,4a,5,5a,6,9,9a,10,10a-decahydro-2H-cyclopenta[b]naphtho[2,3-d]furan-6-carboxylate

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9932	99.32%
Caco-2	-	0.6533	65.33%
Blood Brain Barrier	+	0.7000	70.00%
Human oral bioavailability	-	0.5571	55.71%
Subcellular localzation	Mitochondria	0.7547	75.47%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.7228	72.28%
OATP1B3 inhibitior	-	0.4211	42.11%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.9000	90.00%
BSEP inhibitior	+	0.9628	96.28%
P-glycoprotein inhibitior	+	0.7914	79.14%
P-glycoprotein substrate	+	0.6481	64.81%
CYP3A4 substrate	+	0.7037	70.37%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8771	87.71%
CYP3A4 inhibition	+	0.6769	67.69%
CYP2C9 inhibition	-	0.7241	72.41%
CYP2C19 inhibition	-	0.8330	83.30%
CYP2D6 inhibition	-	0.9179	91.79%
CYP1A2 inhibition	-	0.8582	85.82%
CYP2C8 inhibition	+	0.7464	74.64%
CYP inhibitory promiscuity	-	0.5270	52.70%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9500	95.00%
Carcinogenicity (trinary)	Danger	0.5763	57.63%
Eye corrosion	-	0.9900	99.00%
Eye irritation	-	0.9136	91.36%
Skin irritation	-	0.6640	66.40%
Skin corrosion	-	0.9355	93.55%
Ames mutagenesis	-	0.7400	74.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.6809	68.09%
Micronuclear	-	0.5141	51.41%
Hepatotoxicity	+	0.5849	58.49%
skin sensitisation	-	0.7886	78.86%
Respiratory toxicity	+	0.7667	76.67%
Reproductive toxicity	+	0.9111	91.11%
Mitochondrial toxicity	+	0.6875	68.75%
Nephrotoxicity	-	0.5658	56.58%
Acute Oral Toxicity (c)	III	0.7264	72.64%
Estrogen receptor binding	+	0.8475	84.75%
Androgen receptor binding	+	0.7250	72.50%
Thyroid receptor binding	+	0.6452	64.52%
Glucocorticoid receptor binding	+	0.8486	84.86%
Aromatase binding	+	0.6916	69.16%
PPAR gamma	+	0.7843	78.43%
Honey bee toxicity	-	0.7470	74.70%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	+	0.6100	61.00%
Fish aquatic toxicity	+	0.9776	97.76%

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	98.19%	91.11%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	98.00%	85.14%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	97.18%	96.09%
CHEMBL3137262	O60341	LSD1/CoREST complex	94.65%	97.09%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	93.69%	94.45%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	92.57%	94.00%
CHEMBL221	P23219	Cyclooxygenase-1	90.80%	90.17%
CHEMBL1293277	O15118	Niemann-Pick C1 protein	90.19%	81.11%
CHEMBL4208	P20618	Proteasome component C5	89.80%	90.00%
CHEMBL4040	P28482	MAP kinase ERK2	89.64%	83.82%
CHEMBL1293294	P51151	Ras-related protein Rab-9A	89.49%	87.67%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	87.81%	95.56%
CHEMBL1293249	Q13887	Kruppel-like factor 5	87.68%	86.33%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	86.98%	96.00%
CHEMBL3401	O75469	Pregnane X receptor	85.93%	94.73%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	85.30%	95.50%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	84.69%	94.33%
CHEMBL2581	P07339	Cathepsin D	84.49%	98.95%
CHEMBL1806	P11388	DNA topoisomerase II alpha	84.22%	89.00%
CHEMBL3437	Q16853	Amine oxidase, copper containing	83.18%	94.00%
CHEMBL340	P08684	Cytochrome P450 3A4	82.22%	91.19%
CHEMBL3492	P49721	Proteasome Macropain subunit	81.59%	90.24%
CHEMBL3060	Q9Y345	Glycine transporter 2	80.51%	99.17%

Plants that contains it

• Aristolochia indica
• Azadirachta indica

Cross-Links

• PubChem: 10505484
• NPASS: NPC197137
• ChEMBL: CHEMBL1774398
• LOTUS: LTS0264966
• wikiData: Q27135761