Enniatin B

Details

• Internal ID: 4fec82d5-c14d-402f-81cd-ab9a4ccfc0ba
• Taxonomy: Organic acids and derivatives > Peptidomimetics > Depsipeptides > Cyclic depsipeptides
• IUPAC Name: (3S,6R,9S,12R,15S,18R)-4,10,16-trimethyl-3,6,9,12,15,18-hexa(propan-2-yl)-1,7,13-trioxa-4,10,16-triazacyclooctadecane-2,5,8,11,14,17-hexone
• SMILES (Canonical): CC(C)C1C(=O)OC(C(=O)N(C(C(=O)OC(C(=O)N(C(C(=O)OC(C(=O)N1C)C(C)C)C(C)C)C)C(C)C)C(C)C)C)C(C)C
• SMILES (Isomeric): CC(C)[C@H]1C(=O)O[C@@H](C(=O)N([C@H](C(=O)O[C@@H](C(=O)N([C@H](C(=O)O[C@@H](C(=O)N1C)C(C)C)C(C)C)C)C(C)C)C(C)C)C)C(C)C
• InChI: InChI=1S/C33H57N3O9/c1-16(2)22-31(40)43-26(20(9)10)29(38)35(14)24(18(5)6)33(42)45-27(21(11)12)30(39)36(15)23(17(3)4)32(41)44-25(19(7)8)28(37)34(22)13/h16-27H,1-15H3/t22-,23-,24-,25+,26+,27+/m0/s1
• InChI Key: MIZMDSVSLSIMSC-VYLWARHZSA-N
• Popularity: 212 references in papers

Physical and Chemical Properties

• Molecular Formula: C₃₃H₅₇N₃O₉
• Molecular Weight: 639.80 g/mol
• Exact Mass: 639.40948040 g/mol
• Topological Polar Surface Area (TPSA): 140.00 Ų
• XlogP: 6.50
• Atomic LogP (AlogP): 3.15
• H-Bond Acceptor: 9
• H-Bond Donor: 0
• Rotatable Bonds: 6

Synonyms

• 917-13-5
• 3-N-Methylvaline Enniatin
• UNII-H02S2TZR95
• H02S2TZR95
• (3S,6R,9S,12R,15S,18R)-4,10,16-trimethyl-3,6,9,12,15,18-hexa(propan-2-yl)-1,7,13-trioxa-4,10,16-triazacyclooctadecane-2,5,8,11,14,17-hexone
• CHEBI:64649
• (3S,6R,9S,12R,15S,18R)-3,6,9,12,15,18-hexaisopropyl-4,10,16-trimethyl-1,7,13-trioxa-4,10,16-triazacyclooctadecane-2,5,8,11,14,17-hexone
• Enniatins
• ENNIATIN B [MI]
• MLS000876784
• CHEMBL469036
• MEGxm0_000284
• SCHEMBL20335498
• ACon0_000434
• ACon1_001415
• DTXSID30891862
• C33H57N3O9
• HMS2269N19
• HY-N3806
• AKOS032948909
• C33-H57-N3-O9
• NCGC00180529-01
• BE162722
• SMR000440570
• CS-0024254
• BRD-K01613490-001-01-9
• Q27133360
• (3S,6R,9S,12R,15S,18R)-4,10,16-trimethyl-3,6,9,12,15, 18-hexa(propan-2-yl)-1,7,13-trioxa-4,10,16-triazacyclooctadecane-2,5,8, 11,14,17-hexone
• 2,8,14-Triaza-3,6,9,12,15,18-hexakis(methylethyl)-2,8,14-trimethyl-5,11,17-trioxacyclooctadecane-1,4,7,10,13,16-hexaone
• CYCLO((2R)-2-HYDROXY-3-METHYLBUTANOYL-N-METHYL-L-VALYL-(2R)-2-HYDROXY-3-METHYLBUTANOYL-N-METHYL-L-VALYL-(2R)-2-HYDROXY-3-METHYLBUTANOYL-N-METHYL-L-VALYL)

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.5000	50.00%
Caco-2	-	0.6874	68.74%
Blood Brain Barrier	+	0.6500	65.00%
Human oral bioavailability	+	0.5714	57.14%
Subcellular localzation	Mitochondria	0.5190	51.90%
OATP2B1 inhibitior	-	0.8579	85.79%
OATP1B1 inhibitior	+	0.9378	93.78%
OATP1B3 inhibitior	+	0.9402	94.02%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.9750	97.50%
BSEP inhibitior	-	0.9362	93.62%
P-glycoprotein inhibitior	+	0.6703	67.03%
P-glycoprotein substrate	-	0.8858	88.58%
CYP3A4 substrate	-	0.6264	62.64%
CYP2C9 substrate	+	0.5963	59.63%
CYP2D6 substrate	-	0.8895	88.95%
CYP3A4 inhibition	-	0.9484	94.84%
CYP2C9 inhibition	-	0.9077	90.77%
CYP2C19 inhibition	-	0.9112	91.12%
CYP2D6 inhibition	-	0.9540	95.40%
CYP1A2 inhibition	-	0.9384	93.84%
CYP2C8 inhibition	-	0.9982	99.82%
CYP inhibitory promiscuity	-	0.9883	98.83%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.8007	80.07%
Carcinogenicity (trinary)	Non-required	0.6653	66.53%
Eye corrosion	-	0.9637	96.37%
Eye irritation	-	0.8544	85.44%
Skin irritation	-	0.7918	79.18%
Skin corrosion	-	0.9433	94.33%
Ames mutagenesis	-	0.6300	63.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.6050	60.50%
Micronuclear	+	0.7300	73.00%
Hepatotoxicity	+	0.6801	68.01%
skin sensitisation	-	0.9188	91.88%
Respiratory toxicity	-	0.5111	51.11%
Reproductive toxicity	+	0.6222	62.22%
Mitochondrial toxicity	+	0.5337	53.37%
Nephrotoxicity	+	0.5613	56.13%
Acute Oral Toxicity (c)	III	0.5560	55.60%
Estrogen receptor binding	+	0.7128	71.28%
Androgen receptor binding	-	0.5337	53.37%
Thyroid receptor binding	+	0.5807	58.07%
Glucocorticoid receptor binding	-	0.5442	54.42%
Aromatase binding	+	0.5622	56.22%
PPAR gamma	+	0.5474	54.74%
Honey bee toxicity	-	0.8733	87.33%
Biodegradation	-	0.7500	75.00%
Crustacea aquatic toxicity	-	0.5100	51.00%
Fish aquatic toxicity	-	0.8273	82.73%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL5514	P42858	Huntingtin	3981.1 nM	Potency	via CMAUP
CHEMBL4040	P28482	MAP kinase ERK2	39810.7 nM	Potency	via CMAUP
CHEMBL1293224	P10636	Microtubule-associated protein tau	39810.7 nM	Potency	via CMAUP
CHEMBL5162	Q6W5P4	Neuropeptide S receptor	10000 nM	Potency	via CMAUP
CHEMBL1293277	O15118	Niemann-Pick C1 protein	4466.8 nM	Potency	via CMAUP
CHEMBL1293294	P51151	Ras-related protein Rab-9A	3548.1 nM	Potency	via CMAUP
CHEMBL3797	Q13315	Serine-protein kinase ATM	31622.8 nM	Potency	via CMAUP

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL253	P34972	Cannabinoid CB2 receptor	95.73%	97.25%
CHEMBL2581	P07339	Cathepsin D	91.51%	98.95%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	88.05%	96.09%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	86.87%	95.56%
CHEMBL2265	P23141	Acyl coenzyme A:cholesterol acyltransferase	81.39%	85.94%
CHEMBL1949	P62937	Cyclophilin A	80.31%	98.57%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	80.00%	96.77%

Plants that contains it

• Alcea rosea
• Alpinia roxburghii
• Balanops australiana
• Davallia perdurans
• Euonymus tingens
• Euphorbia cornigera
• Gonzalezia decurrens
• Hylocomium splendens
• Kokoona reflexa
• Maesa ramentacea
• Millettia laurentii
• Monodora tenuifolia
• Ocimum tenuiflorum
• Pinus strobus
• Pinus sylvestris
• Pluchea odorata
• Salacia lehmbachii
• Salvia yosgadensis
• Sideritis brevibracteata
• Sideroxylon cubense

Cross-Links

• PubChem: 164754
• NPASS: NPC212866
• ChEMBL: CHEMBL469036
• LOTUS: LTS0007312
• wikiData: Q27133360