Metabolite Sacubitrilat (LBQ657)

Name

Sacubitrilat (LBQ657)

Description

Sacubitrilat is the active metabolite of the antihypertensive drug sacubitril, which is used in the treatment of heart failure.

Structure

Similar Structures

Synonyms

Not Available

UNII

Not Available

CAS number

149709-44-4

Weight

Average: 383.444
Monoisotopic: 383.173272909

Chemical Formula

C₂₂H₂₅NO₅

InChI Key

DOBNVUFHFMVMDB-BEFAXECRSA-N

InChI

InChI=1S/C22H25NO5/c1-15(22(27)28)13-19(23-20(24)11-12-21(25)26)14-16-7-9-18(10-8-16)17-5-3-2-4-6-17/h2-10,15,19H,11-14H2,1H3,(H,23,24)(H,25,26)(H,27,28)/t15-,19+/m1/s1

IUPAC Name

(2R,4S)-5-{[1,1'-biphenyl]-4-yl}-4-(3-carboxypropanamido)-2-methylpentanoic acid

SMILES

[H][C@@](C)(C[C@@]([H])(CC1=CC=C(C=C1)C1=CC=CC=C1)NC(=O)CCC(O)=O)C(O)=O

Reactions

Sacubitril

Sacubitrilat (LBQ657)

Spectra

Spectrum	Spectrum Type	Splash Key
Predicted MS/MS Spectrum - 10V, Positive (Annotated)	Predicted LC-MS/MS	splash10-01c0-0092000000-2ebc8aa4222fd1d26f70
Predicted MS/MS Spectrum - 10V, Negative (Annotated)	Predicted LC-MS/MS	splash10-001i-4090000000-6d28c15b95b968331200
Predicted MS/MS Spectrum - 20V, Positive (Annotated)	Predicted LC-MS/MS	splash10-00s9-2290000000-046b7c42df2760b7dc4a
Predicted MS/MS Spectrum - 20V, Negative (Annotated)	Predicted LC-MS/MS	splash10-0006-1090000000-d14802e69fbb2e90572c
Predicted MS/MS Spectrum - 40V, Negative (Annotated)	Predicted LC-MS/MS	splash10-0076-8191000000-0ec440bd3dd0a9237b0c
Predicted MS/MS Spectrum - 40V, Positive (Annotated)	Predicted LC-MS/MS	splash10-05w0-4691000000-3ca08017c2c4e2f26808
Predicted MS/MS Spectrum - 10V, Positive (Annotated)	Predicted LC-MS/MS	splash10-01c0-0092000000-9d44f0ad862a3e69bc7f
Predicted MS/MS Spectrum - 10V, Negative (Annotated)	Predicted LC-MS/MS	splash10-001l-7296000000-6f83ee2d9739b54ab933
Predicted MS/MS Spectrum - 20V, Positive (Annotated)	Predicted LC-MS/MS	splash10-00di-2391000000-6335cc965e5a3720c0dd
Predicted MS/MS Spectrum - 40V, Positive (Annotated)	Predicted LC-MS/MS	splash10-05p9-3791000000-c4e123995b71e1848195
Predicted MS/MS Spectrum - 20V, Negative (Annotated)	Predicted LC-MS/MS	splash10-000f-1091000000-5204dd34bc8a630a0444
Predicted MS/MS Spectrum - 40V, Negative (Annotated)	Predicted LC-MS/MS	splash10-007c-3290000000-fea49acc90f2b6ce4b25
Predicted 1H NMR Spectrum	1D NMR	Not Applicable
Predicted 13C NMR Spectrum	1D NMR	Not Applicable

Chromatographic Properties

Collision Cross Sections (CCS)

Adduct	CCS Value (Å²)	Source type	Source
[M-H]-	208.4374422	predicted	DarkChem Lite v0.1.0
[M-H]-	187.36949	predicted	DeepCCS 1.0 (2019)
[M-H]-	208.4374422	predicted	DarkChem Lite v0.1.0
[M-H]-	187.36949	predicted	DeepCCS 1.0 (2019)
[M+H]+	205.6272422	predicted	DarkChem Lite v0.1.0
[M+H]+	189.76506	predicted	DeepCCS 1.0 (2019)
[M+H]+	205.6272422	predicted	DarkChem Lite v0.1.0
[M+H]+	189.76506	predicted	DeepCCS 1.0 (2019)
[M+Na]+	206.1276422	predicted	DarkChem Lite v0.1.0
[M+Na]+	195.67758	predicted	DeepCCS 1.0 (2019)
[M+Na]+	206.1276422	predicted	DarkChem Lite v0.1.0
[M+Na]+	195.67758	predicted	DeepCCS 1.0 (2019)

External Links

ChemSpider: 8605468
BindingDB: 50034842
ChEMBL: CHEMBL417007
ZINC: ZINC000001536201
PDBe Ligand: 6LD
Wikipedia: Sacubitrilat

Predicted Properties

Property	Value	Source
Water Solubility	0.00358 mg/mL	ALOGPS
logP	1.99	ALOGPS
logP	3.29	Chemaxon
logS	-5	ALOGPS
pKa (Strongest Acidic)	3.98	Chemaxon
pKa (Strongest Basic)	-1.6	Chemaxon
Physiological Charge	-2	Chemaxon
Hydrogen Acceptor Count	5	Chemaxon
Hydrogen Donor Count	3	Chemaxon
Polar Surface Area	103.7 Å²	Chemaxon
Rotatable Bond Count	10	Chemaxon
Refractivity	104.54 m³·mol^-1	Chemaxon
Polarizability	41.61 Å³	Chemaxon
Number of Rings	2	Chemaxon
Bioavailability	1	Chemaxon
Rule of Five	Yes	Chemaxon
Ghose Filter	Yes	Chemaxon
Veber's Rule	No	Chemaxon
MDDR-like Rule	No	Chemaxon

Metabolite Sacubitrilat (LBQ657)

Structure for Sacubitrilat (LBQ657)

Collision Cross Sections (CCS)