Anisomycin

Details

• Internal ID: bb2e2ab0-7899-4177-86c2-2d09a5df1662
• Taxonomy: Benzenoids > Phenol ethers > Anisoles
• IUPAC Name: [(2R,3S,4S)-4-hydroxy-2-[(4-methoxyphenyl)methyl]pyrrolidin-3-yl] acetate
• SMILES (Canonical): CC(=O)OC1C(CNC1CC2=CC=C(C=C2)OC)O
• SMILES (Isomeric): CC(=O)O[C@@H]1[C@H](CN[C@@H]1CC2=CC=C(C=C2)OC)O
• InChI: InChI=1S/C14H19NO4/c1-9(16)19-14-12(15-8-13(14)17)7-10-3-5-11(18-2)6-4-10/h3-6,12-15,17H,7-8H2,1-2H3/t12-,13+,14+/m1/s1
• InChI Key: YKJYKKNCCRKFSL-RDBSUJKOSA-N
• Popularity: 2,660 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₄H₁₉NO₄
• Molecular Weight: 265.30 g/mol
• Exact Mass: 265.13140809 g/mol
• Topological Polar Surface Area (TPSA): 67.80 Ų
• XlogP: 0.90
• Atomic LogP (AlogP): 0.50
• H-Bond Acceptor: 5
• H-Bond Donor: 2
• Rotatable Bonds: 4

Synonyms

• 22862-76-6
• Flagecidin
• (-)-Anisomycin
• (2R,3S,4S)-4-hydroxy-2-(4-methoxybenzyl)pyrrolidin-3-yl acetate
• TCMDC-125504
• Upjohn 204t3
• (2R,3S,4S)-2-(p-Methoxybenzyl)-3,4-pyrrolidinediol 3-acetate
• NSC-76712
• NSC76712
• NSC 76712
• Anisomycin from Streptomyces griseolus
• 2-(p-Methoxybenzyl)-3,4-pyrrolidinediol 3-acetate
• 6C74YM2NGI
• [(2R,3S,4S)-4-hydroxy-2-[(4-methoxyphenyl)methyl]pyrrolidin-3-yl] acetate
• MLS001066392
• CHEBI:338412
• (2R,3S,4S)-2-[(4-Methoxyphenyl)methyl]-3,4-pyrrolidinediol 3-acetate
• 1,4,5-Trideoxy-1,4-imino-5-(p-methoxyphenyl)-D-xylo-pentitol 3-acetate
• SMR000471874
• (2R,3S,4S)-2-((4-Methoxyphenyl)methyl)-3,4-pyrrolidinediol 3-acetate
• (2R,3S,4S)-2-(p-Methoxyphenylmethyl)-3-acetoxy-4-hydroxypyrrolidine
• 3,4-Pyrrolidinediol, 2-((4-methoxyphenyl)methyl)-, 3-acetate, (2R,3S,4S)-
• 3,4-Pyrrolidinediol, 2-[(4-methoxyphenyl)methyl]-, 3-acetate, (2R,3S,4S)-
• 3,4-Pyrrolidinediol, 2-[(4-methoxyphenyl)methyl]-, 3-acetate,(2R,3S,4S)-
• 2-p-Methoxyphenylmethyl-3-acetoxy-4-hydroxypyrrolidine
• ANM
• Flagecidin;Wuningmeisu C
• Antibiotic PA-106
• SR-01000597397
• GNF-Pf-4549
• UNII-6C74YM2NGI
• Wuningmeisu C
• Anisomycin,streptomyces griseolus
• 6185-RBK-10
• (-) Anisomycin
• 2-(p-Methoxybenzyl)-3,4-pyrrolidinediol-3-acetate
• EINECS 245-269-7
• MFCD00077650
• BRN 0020705
• Spectrum_001534
• ANISOMYCIN [MI]
• AI3-50846
• Prestwick3_000412
• Spectrum2_000632
• Spectrum4_000748
• Spectrum5_001495
• ANISOMYCIN, (-)-
• CBiol_002064
• BSPBio_000364
• BSPBio_001436
• KBioGR_001076
• KBioSS_002014
• 5-21-05-00523 (Beilstein Handbook Reference)
• DivK1c_000855
• SPECTRUM1503906
• SPBio_000624
• BPBio1_000402
• CHEMBL423192
• cid_253602
• SCHEMBL2270183
• DTXSID5040966
• BDBM63919
• HMS502K17
• KBio1_000855
• KBio2_002014
• KBio2_004582
• KBio2_007150
• NINDS_000855
• YKJYKKNCCRKFSL-RDBSUJKOSA-N
• Bio1_000350
• Bio1_000839
• Bio1_001328
• HMS1922K06
• HMS2096C06
• HMS2231E05
• HMS3267L11
• HMS3414L17
• HMS3678L15
• CCG-39185
• HB2239
• AKOS015916532
• CS-4981
• DB07374
• SDCCGMLS-0066810.P001
• 3,4-Pyrrolidinediol, 2-((4-methoxyphenyl)methyl)-, 3-acetate, (2R-(2alpha,3alpha,4beta))-
• IDI1_000855
• QTL1_000009
• NCGC00025097-02
• NCGC00025097-03
• NCGC00025097-04
• 3,4-Pyrrolidinediol, 2-((4-methoxyphenyl)methyl)-, 3-acetate, (2R-(2-alpha,3-alpha,4-beta))-
• AC-35125
• AS-44380
• HY-18982
• NCI60_041689
• AB00513833
• A-7940
• A927918
• Anisomycin, Antibiotic for Culture Media Use Only
• Q378498
• SR-01000597397-1
• SR-01000597397-3
• BRD-K91370081-001-04-6
• BRD-K91370081-001-17-8
• 3, 2-(p-methoxybenzyl)-, 3-acetate, (2S,3R,4R)-
• Anisomycin from Streptomyces griseolus, >=98% (HPLC), solid
• (2R,3S,4S)-2-(4-Methoxybenzyl)-3,4-pyrrolidinediol 3-Acetate
• (2R,3S,4S)-4-hydroxy-2-(4-methoxybenzyl)pyrrolidin-3-ylacetate
• (2R,3S,4S)-4-hydroxy-2-[(4-methoxyphenyl)methyl]pyrrolidin-3-yl acetate
• acetic acid [(2R,3S,4S)-4-hydroxy-2-p-anisyl-pyrrolidin-3-yl] ester
• Rel-(2R,3S,4S)-4-hydroxy-2-(4-methoxybenzyl)pyrrolidin-3-yl acetate
• [(2R,3S,4S)-2-[(4-methoxyphenyl)methyl]-4-oxidanyl-pyrrolidin-3-yl] ethanoate
• 3, 2-[(4-methoxyphenyl)methyl]-, 3-acetate, [2S-(2.alpha.,3.alpha.,4.beta.)]-
• acetic acid [(2R,3S,4S)-4-hydroxy-2-[(4-methoxyphenyl)methyl]-3-pyrrolidinyl] ester
• [[4-[2-[[(3-Ethyl-2,5-dihydro-4-methyl-2-oxo-1H-pyrrol-1-yl)carbonyl]amino]ethyl]phenyl]sulfonyl]carbamicacidethylester
• 11023-48-6
• 21497-40-5

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.7928	79.28%
Caco-2	+	0.7278	72.78%
Blood Brain Barrier	-	0.7250	72.50%
Human oral bioavailability	-	0.5429	54.29%
Subcellular localzation	Mitochondria	0.7638	76.38%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9414	94.14%
OATP1B3 inhibitior	+	0.9480	94.80%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.8500	85.00%
BSEP inhibitior	-	0.8392	83.92%
P-glycoprotein inhibitior	-	0.8419	84.19%
P-glycoprotein substrate	-	0.7667	76.67%
CYP3A4 substrate	+	0.5664	56.64%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	+	0.4419	44.19%
CYP3A4 inhibition	-	0.9726	97.26%
CYP2C9 inhibition	-	0.9070	90.70%
CYP2C19 inhibition	-	0.9025	90.25%
CYP2D6 inhibition	+	0.8932	89.32%
CYP1A2 inhibition	-	0.9045	90.45%
CYP2C8 inhibition	-	0.8132	81.32%
CYP inhibitory promiscuity	-	0.8681	86.81%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.9100	91.00%
Carcinogenicity (trinary)	Non-required	0.7013	70.13%
Eye corrosion	-	0.9907	99.07%
Eye irritation	-	0.9540	95.40%
Skin irritation	-	0.7666	76.66%
Skin corrosion	-	0.9268	92.68%
Ames mutagenesis	-	0.6600	66.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7940	79.40%
Micronuclear	+	0.6500	65.00%
Hepatotoxicity	-	0.6108	61.08%
skin sensitisation	-	0.8586	85.86%
Respiratory toxicity	+	0.5667	56.67%
Reproductive toxicity	+	0.7778	77.78%
Mitochondrial toxicity	+	0.7875	78.75%
Nephrotoxicity	-	0.8829	88.29%
Acute Oral Toxicity (c)	II	0.7371	73.71%
Estrogen receptor binding	-	0.5812	58.12%
Androgen receptor binding	-	0.6292	62.92%
Thyroid receptor binding	-	0.6165	61.65%
Glucocorticoid receptor binding	-	0.5775	57.75%
Aromatase binding	-	0.5599	55.99%
PPAR gamma	-	0.8131	81.31%
Honey bee toxicity	-	0.9071	90.71%
Biodegradation	-	0.7000	70.00%
Crustacea aquatic toxicity	-	0.5700	57.00%
Fish aquatic toxicity	-	0.6938	69.38%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL4040	P28482	MAP kinase ERK2	50.1 nM	Potency	via Super-PRED
CHEMBL1293235	P02545	Prelamin-A/C	63.1 nM	Potency	via Super-PRED
CHEMBL1293232	Q16637	Survival motor neuron protein	12.6 nM; 707.9 nM; 100 nM	Potency; Potency; Potency	via Super-PRED; via Super-PRED; via Super-PRED

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	99.17%	96.09%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	97.42%	94.45%
CHEMBL2581	P07339	Cathepsin D	93.99%	98.95%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	92.86%	91.11%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	92.30%	96.95%
CHEMBL4208	P20618	Proteasome component C5	91.75%	90.00%
CHEMBL3137262	O60341	LSD1/CoREST complex	90.03%	97.09%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	89.27%	95.56%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	88.39%	85.14%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	87.57%	95.50%
CHEMBL5608	Q16288	NT-3 growth factor receptor	87.54%	95.89%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	84.50%	95.89%
CHEMBL3060	Q9Y345	Glycine transporter 2	84.44%	99.17%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	83.70%	94.00%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	83.60%	92.62%
CHEMBL3922	P50579	Methionine aminopeptidase 2	82.43%	97.28%
CHEMBL4657	Q6V1X1	Dipeptidyl peptidase VIII	81.41%	97.21%

Plants that contains it

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Cross-Links

• PubChem: 253602
• LOTUS: LTS0195167
• wikiData: Q378498