NP-MRD: Showing NP-Card for (3R,6R)-N-methyl-N-(1-hydroxy-2-methylpropyl)-phenylalanine (NP0004142)

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Record Information

Version

2.0

Created at

2020-12-09 01:38:11 UTC

Updated at

2021-07-15 16:48:21 UTC

NP-MRD ID

NP0004142

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(3R,6R)-N-methyl-N-(1-hydroxy-2-methylpropyl)-phenylalanine

Provided By

NPAtlas

Description

(2R)-2-[(2R)-2-hydroxy-N,3-dimethylbutanamido]-3-phenylpropanoic acid belongs to the class of organic compounds known as phenylalanine and derivatives. Phenylalanine and derivatives are compounds containing phenylalanine or a derivative thereof resulting from reaction of phenylalanine at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom. (3R,6R)-N-methyl-N-(1-hydroxy-2-methylpropyl)-phenylalanine is found in Isaria japonica. Based on a literature review very few articles have been published on (2R)-2-[(2R)-2-hydroxy-N,3-dimethylbutanamido]-3-phenylpropanoic acid.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306242118043D          

 41 41  0  0  0  0            999 V2000
    2.8888   -0.6363    1.8122 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3795    0.7316    1.4934 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.5638    1.6719    1.3898 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6919    0.7433    0.1195 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.6480    0.3591   -0.7843 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4867   -0.0784    0.1186 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4247    0.2671    0.9465 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2700   -1.1766   -0.6961 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.3289   -1.6219   -1.6015 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9822   -1.9158   -0.7533 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.0830   -1.2202   -1.4978 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.5242    0.0768   -1.0348 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9573    1.2263   -1.6038 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3587    2.4789   -1.1933 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3186    2.6598   -0.2219 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8798    1.5338    0.3414 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4821    0.2831   -0.0655 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3709   -2.4889    0.5408 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4217   -3.1577    0.6785 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5763   -2.3036    1.6604 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3589   -1.4469    1.3029 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7817   -0.8089    2.9200 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9905   -0.7341    1.6267 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6752    1.0776    2.2743 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4730    1.0811    1.1649 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3696    2.4871    0.6815 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7528    2.1516    2.3855 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4188    1.8218   -0.0974 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2881    1.0816   -0.9641 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2461   -1.8502   -1.0602 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4997   -0.8255   -2.3371 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9835   -2.5037   -2.2034 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7553   -2.8087   -1.4445 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9522   -1.9494   -1.5105 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7732   -1.2062   -2.5904 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1992    1.1438   -2.3707 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9272    3.3724   -1.6263 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6288    3.6689    0.0955 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6319    1.6828    1.1024 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9452   -0.5863    0.3996 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9028   -2.2809    2.6026 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  2  4  1  0  0  0  0
  4  5  1  0  0  0  0
  4  6  1  0  0  0  0
  6  7  2  0  0  0  0
  6  8  1  0  0  0  0
  8  9  1  0  0  0  0
  8 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 10 18  1  0  0  0  0
 18 19  2  0  0  0  0
 18 20  1  0  0  0  0
 17 12  1  0  0  0  0
  1 21  1  0  0  0  0
  1 22  1  0  0  0  0
  1 23  1  0  0  0  0
  2 24  1  1  0  0  0
  3 25  1  0  0  0  0
  3 26  1  0  0  0  0
  3 27  1  0  0  0  0
  4 28  1  6  0  0  0
  5 29  1  0  0  0  0
  9 30  1  0  0  0  0
  9 31  1  0  0  0  0
  9 32  1  0  0  0  0
 10 33  1  6  0  0  0
 11 34  1  0  0  0  0
 11 35  1  0  0  0  0
 13 36  1  0  0  0  0
 14 37  1  0  0  0  0
 15 38  1  0  0  0  0
 16 39  1  0  0  0  0
 17 40  1  0  0  0  0
 20 41  1  0  0  0  0
M  END

     RDKit          3D

 41 41  0  0  0  0  0  0  0  0999 V2000
    2.8888   -0.6363    1.8122 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3795    0.7316    1.4934 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.5638    1.6719    1.3898 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6919    0.7433    0.1195 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.6480    0.3591   -0.7843 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4867   -0.0784    0.1186 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4247    0.2671    0.9465 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2700   -1.1766   -0.6961 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.3289   -1.6219   -1.6015 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9822   -1.9158   -0.7533 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.0830   -1.2202   -1.4978 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5242    0.0768   -1.0348 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9573    1.2263   -1.6038 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3587    2.4789   -1.1933 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3186    2.6598   -0.2219 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8798    1.5338    0.3414 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4821    0.2831   -0.0655 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3709   -2.4889    0.5408 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4217   -3.1577    0.6785 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5763   -2.3036    1.6604 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3589   -1.4469    1.3029 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7817   -0.8089    2.9200 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9905   -0.7341    1.6267 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6752    1.0776    2.2743 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4730    1.0811    1.1649 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3696    2.4871    0.6815 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7528    2.1516    2.3855 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4188    1.8218   -0.0974 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2881    1.0816   -0.9641 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2461   -1.8502   -1.0602 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4997   -0.8255   -2.3371 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9835   -2.5037   -2.2034 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7553   -2.8087   -1.4445 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9522   -1.9494   -1.5105 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7732   -1.2062   -2.5904 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1992    1.1438   -2.3707 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9272    3.3724   -1.6263 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6288    3.6689    0.0955 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6319    1.6828    1.1024 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9452   -0.5863    0.3996 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9028   -2.2809    2.6026 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  4  6  1  0
  6  7  2  0
  6  8  1  0
  8  9  1  0
  8 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 10 18  1  0
 18 19  2  0
 18 20  1  0
 17 12  1  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
  2 24  1  1
  3 25  1  0
  3 26  1  0
  3 27  1  0
  4 28  1  6
  5 29  1  0
  9 30  1  0
  9 31  1  0
  9 32  1  0
 10 33  1  6
 11 34  1  0
 11 35  1  0
 13 36  1  0
 14 37  1  0
 15 38  1  0
 16 39  1  0
 17 40  1  0
 20 41  1  0
M  END


  Mrv1652306242118043D          

 41 41  0  0  0  0            999 V2000
    2.8888   -0.6363    1.8122 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3795    0.7316    1.4934 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.5638    1.6719    1.3898 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6919    0.7433    0.1195 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.6480    0.3591   -0.7843 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4867   -0.0784    0.1186 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4247    0.2671    0.9465 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2700   -1.1766   -0.6961 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.3289   -1.6219   -1.6015 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9822   -1.9158   -0.7533 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.0830   -1.2202   -1.4978 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.5242    0.0768   -1.0348 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9573    1.2263   -1.6038 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3587    2.4789   -1.1933 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3186    2.6598   -0.2219 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8798    1.5338    0.3414 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4821    0.2831   -0.0655 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3709   -2.4889    0.5408 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4217   -3.1577    0.6785 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5763   -2.3036    1.6604 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3589   -1.4469    1.3029 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7817   -0.8089    2.9200 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9905   -0.7341    1.6267 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6752    1.0776    2.2743 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4730    1.0811    1.1649 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3696    2.4871    0.6815 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7528    2.1516    2.3855 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4188    1.8218   -0.0974 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2881    1.0816   -0.9641 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2461   -1.8502   -1.0602 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4997   -0.8255   -2.3371 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9835   -2.5037   -2.2034 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7553   -2.8087   -1.4445 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9522   -1.9494   -1.5105 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7732   -1.2062   -2.5904 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1992    1.1438   -2.3707 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9272    3.3724   -1.6263 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6288    3.6689    0.0955 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6319    1.6828    1.1024 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9452   -0.5863    0.3996 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9028   -2.2809    2.6026 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  2  4  1  0  0  0  0
  4  5  1  0  0  0  0
  4  6  1  0  0  0  0
  6  7  2  0  0  0  0
  6  8  1  0  0  0  0
  8  9  1  0  0  0  0
  8 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 10 18  1  0  0  0  0
 18 19  2  0  0  0  0
 18 20  1  0  0  0  0
 17 12  1  0  0  0  0
  1 21  1  0  0  0  0
  1 22  1  0  0  0  0
  1 23  1  0  0  0  0
  2 24  1  1  0  0  0
  3 25  1  0  0  0  0
  3 26  1  0  0  0  0
  3 27  1  0  0  0  0
  4 28  1  6  0  0  0
  5 29  1  0  0  0  0
  9 30  1  0  0  0  0
  9 31  1  0  0  0  0
  9 32  1  0  0  0  0
 10 33  1  6  0  0  0
 11 34  1  0  0  0  0
 11 35  1  0  0  0  0
 13 36  1  0  0  0  0
 14 37  1  0  0  0  0
 15 38  1  0  0  0  0
 16 39  1  0  0  0  0
 17 40  1  0  0  0  0
 20 41  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0004142

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC(=O)[C@]([H])(N(C(=O)[C@]([H])(O[H])C([H])(C([H])([H])[H])C([H])([H])[H])C([H])([H])[H])C([H])([H])C1=C([H])C([H])=C([H])C([H])=C1[H]

> <INCHI_IDENTIFIER>
InChI=1S/C15H21NO4/c1-10(2)13(17)14(18)16(3)12(15(19)20)9-11-7-5-4-6-8-11/h4-8,10,12-13,17H,9H2,1-3H3,(H,19,20)/t12-,13-/m1/s1

> <INCHI_KEY>
AFSFYXHJJVYLOJ-CHWSQXEVSA-N

> <FORMULA>
C15H21NO4

> <MOLECULAR_WEIGHT>
279.336

> <EXACT_MASS>
279.14705816

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
41

> <JCHEM_AVERAGE_POLARIZABILITY>
28.95268247189864

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2R)-2-[(2R)-2-hydroxy-N,3-dimethylbutanamido]-3-phenylpropanoic acid

> <ALOGPS_LOGP>
1.37

> <JCHEM_LOGP>
1.7591491393333336

> <ALOGPS_LOGS>
-2.29

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
12.947841167945576

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.1099573897107256

> <JCHEM_PKA_STRONGEST_BASIC>
-3.6980800126859084

> <JCHEM_POLAR_SURFACE_AREA>
77.84

> <JCHEM_REFRACTIVITY>
74.64850000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.42e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2R)-2-[(2R)-2-hydroxy-N,3-dimethylbutanamido]-3-phenylpropanoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 41 41  0  0  0  0  0  0  0  0999 V2000
    2.8888   -0.6363    1.8122 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3795    0.7316    1.4934 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.5638    1.6719    1.3898 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6919    0.7433    0.1195 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.6480    0.3591   -0.7843 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4867   -0.0784    0.1186 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4247    0.2671    0.9465 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2700   -1.1766   -0.6961 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.3289   -1.6219   -1.6015 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9822   -1.9158   -0.7533 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.0830   -1.2202   -1.4978 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5242    0.0768   -1.0348 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9573    1.2263   -1.6038 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3587    2.4789   -1.1933 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3186    2.6598   -0.2219 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8798    1.5338    0.3414 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4821    0.2831   -0.0655 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3709   -2.4889    0.5408 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4217   -3.1577    0.6785 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5763   -2.3036    1.6604 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3589   -1.4469    1.3029 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7817   -0.8089    2.9200 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9905   -0.7341    1.6267 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6752    1.0776    2.2743 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4730    1.0811    1.1649 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3696    2.4871    0.6815 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7528    2.1516    2.3855 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4188    1.8218   -0.0974 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2881    1.0816   -0.9641 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2461   -1.8502   -1.0602 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4997   -0.8255   -2.3371 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9835   -2.5037   -2.2034 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7553   -2.8087   -1.4445 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9522   -1.9494   -1.5105 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7732   -1.2062   -2.5904 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1992    1.1438   -2.3707 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9272    3.3724   -1.6263 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6288    3.6689    0.0955 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6319    1.6828    1.1024 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9452   -0.5863    0.3996 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9028   -2.2809    2.6026 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  4  6  1  0
  6  7  2  0
  6  8  1  0
  8  9  1  0
  8 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 10 18  1  0
 18 19  2  0
 18 20  1  0
 17 12  1  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
  2 24  1  1
  3 25  1  0
  3 26  1  0
  3 27  1  0
  4 28  1  6
  5 29  1  0
  9 30  1  0
  9 31  1  0
  9 32  1  0
 10 33  1  6
 11 34  1  0
 11 35  1  0
 13 36  1  0
 14 37  1  0
 15 38  1  0
 16 39  1  0
 17 40  1  0
 20 41  1  0
M  END

HEADER    PROTEIN                                 24-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-JUN-21         0                                  
HETATM    1  C   UNK     0       2.889  -0.636   1.812  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.380   0.732   1.493  0.00  0.00           C+0
HETATM    3  C   UNK     0       3.564   1.672   1.390  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.692   0.743   0.120  0.00  0.00           C+0
HETATM    5  O   UNK     0       2.648   0.359  -0.784  0.00  0.00           O+0
HETATM    6  C   UNK     0       0.487  -0.078   0.119  0.00  0.00           C+0
HETATM    7  O   UNK     0      -0.425   0.267   0.947  0.00  0.00           O+0
HETATM    8  N   UNK     0       0.270  -1.177  -0.696  0.00  0.00           N+0
HETATM    9  C   UNK     0       1.329  -1.622  -1.601  0.00  0.00           C+0
HETATM   10  C   UNK     0      -0.982  -1.916  -0.753  0.00  0.00           C+0
HETATM   11  C   UNK     0      -2.083  -1.220  -1.498  0.00  0.00           C+0
HETATM   12  C   UNK     0      -2.524   0.077  -1.035  0.00  0.00           C+0
HETATM   13  C   UNK     0      -1.957   1.226  -1.604  0.00  0.00           C+0
HETATM   14  C   UNK     0      -2.359   2.479  -1.193  0.00  0.00           C+0
HETATM   15  C   UNK     0      -3.319   2.660  -0.222  0.00  0.00           C+0
HETATM   16  C   UNK     0      -3.880   1.534   0.341  0.00  0.00           C+0
HETATM   17  C   UNK     0      -3.482   0.283  -0.066  0.00  0.00           C+0
HETATM   18  C   UNK     0      -1.371  -2.489   0.541  0.00  0.00           C+0
HETATM   19  O   UNK     0      -2.422  -3.158   0.679  0.00  0.00           O+0
HETATM   20  O   UNK     0      -0.576  -2.304   1.660  0.00  0.00           O+0
HETATM   21  H   UNK     0       2.359  -1.447   1.303  0.00  0.00           H+0
HETATM   22  H   UNK     0       2.782  -0.809   2.920  0.00  0.00           H+0
HETATM   23  H   UNK     0       3.990  -0.734   1.627  0.00  0.00           H+0
HETATM   24  H   UNK     0       1.675   1.078   2.274  0.00  0.00           H+0
HETATM   25  H   UNK     0       4.473   1.081   1.165  0.00  0.00           H+0
HETATM   26  H   UNK     0       3.370   2.487   0.682  0.00  0.00           H+0
HETATM   27  H   UNK     0       3.753   2.152   2.385  0.00  0.00           H+0
HETATM   28  H   UNK     0       1.419   1.822  -0.097  0.00  0.00           H+0
HETATM   29  H   UNK     0       3.288   1.082  -0.964  0.00  0.00           H+0
HETATM   30  H   UNK     0       2.246  -1.850  -1.060  0.00  0.00           H+0
HETATM   31  H   UNK     0       1.500  -0.826  -2.337  0.00  0.00           H+0
HETATM   32  H   UNK     0       0.984  -2.504  -2.203  0.00  0.00           H+0
HETATM   33  H   UNK     0      -0.755  -2.809  -1.444  0.00  0.00           H+0
HETATM   34  H   UNK     0      -2.952  -1.949  -1.510  0.00  0.00           H+0
HETATM   35  H   UNK     0      -1.773  -1.206  -2.590  0.00  0.00           H+0
HETATM   36  H   UNK     0      -1.199   1.144  -2.371  0.00  0.00           H+0
HETATM   37  H   UNK     0      -1.927   3.372  -1.626  0.00  0.00           H+0
HETATM   38  H   UNK     0      -3.629   3.669   0.096  0.00  0.00           H+0
HETATM   39  H   UNK     0      -4.632   1.683   1.102  0.00  0.00           H+0
HETATM   40  H   UNK     0      -3.945  -0.586   0.400  0.00  0.00           H+0
HETATM   41  H   UNK     0      -0.903  -2.281   2.603  0.00  0.00           H+0
CONECT    1    2   21   22   23                                             
CONECT    2    1    3    4   24                                             
CONECT    3    2   25   26   27                                             
CONECT    4    2    5    6   28                                             
CONECT    5    4   29                                                       
CONECT    6    4    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9   10                                                  
CONECT    9    8   30   31   32                                             
CONECT   10    8   11   18   33                                             
CONECT   11   10   12   34   35                                             
CONECT   12   11   13   17                                                  
CONECT   13   12   14   36                                                  
CONECT   14   13   15   37                                                  
CONECT   15   14   16   38                                                  
CONECT   16   15   17   39                                                  
CONECT   17   16   12   40                                                  
CONECT   18   10   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18   41                                                       
CONECT   21    1                                                            
CONECT   22    1                                                            
CONECT   23    1                                                            
CONECT   24    2                                                            
CONECT   25    3                                                            
CONECT   26    3                                                            
CONECT   27    3                                                            
CONECT   28    4                                                            
CONECT   29    5                                                            
CONECT   30    9                                                            
CONECT   31    9                                                            
CONECT   32    9                                                            
CONECT   33   10                                                            
CONECT   34   11                                                            
CONECT   35   11                                                            
CONECT   36   13                                                            
CONECT   37   14                                                            
CONECT   38   15                                                            
CONECT   39   16                                                            
CONECT   40   17                                                            
CONECT   41   20                                                            
MASTER        0    0    0    0    0    0    0    0   41    0   82    0
END

RDKit          3D

41 41  0  0  0  0  0  0  0  0999 V2000
    2.8888   -0.6363    1.8122 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3795    0.7316    1.4934 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.5638    1.6719    1.3898 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6919    0.7433    0.1195 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.6480    0.3591   -0.7843 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4867   -0.0784    0.1186 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4247    0.2671    0.9465 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2700   -1.1766   -0.6961 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.3289   -1.6219   -1.6015 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9822   -1.9158   -0.7533 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.0830   -1.2202   -1.4978 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5242    0.0768   -1.0348 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9573    1.2263   -1.6038 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3587    2.4789   -1.1933 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3186    2.6598   -0.2219 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8798    1.5338    0.3414 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4821    0.2831   -0.0655 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3709   -2.4889    0.5408 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4217   -3.1577    0.6785 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5763   -2.3036    1.6604 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3589   -1.4469    1.3029 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7817   -0.8089    2.9200 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9905   -0.7341    1.6267 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6752    1.0776    2.2743 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4730    1.0811    1.1649 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3696    2.4871    0.6815 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7528    2.1516    2.3855 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4188    1.8218   -0.0974 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2881    1.0816   -0.9641 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2461   -1.8502   -1.0602 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4997   -0.8255   -2.3371 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9835   -2.5037   -2.2034 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7553   -2.8087   -1.4445 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9522   -1.9494   -1.5105 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7732   -1.2062   -2.5904 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1992    1.1438   -2.3707 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9272    3.3724   -1.6263 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6288    3.6689    0.0955 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6319    1.6828    1.1024 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9452   -0.5863    0.3996 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9028   -2.2809    2.6026 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  4  6  1  0
  6  7  2  0
  6  8  1  0
  8  9  1  0
  8 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 10 18  1  0
 18 19  2  0
 18 20  1  0
 17 12  1  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
  2 24  1  1
  3 25  1  0
  3 26  1  0
  3 27  1  0
  4 28  1  6
  5 29  1  0
  9 30  1  0
  9 31  1  0
  9 32  1  0
 10 33  1  6
 11 34  1  0
 11 35  1  0
 13 36  1  0
 14 37  1  0
 15 38  1  0
 16 39  1  0
 17 40  1  0
 20 41  1  0
M  END

View in JSmol View NMR Assignments

Synonyms

Value	Source
(2R)-2-[(2R)-2-Hydroxy-N,3-dimethylbutanamido]-3-phenylpropanoate	Generator

Chemical Formula

C₁₅H₂₁NO₄

Average Mass

279.3360 Da

Monoisotopic Mass

279.14706 Da

IUPAC Name

(2R)-2-[(2R)-2-hydroxy-N,3-dimethylbutanamido]-3-phenylpropanoic acid

Traditional Name

(2R)-2-[(2R)-2-hydroxy-N,3-dimethylbutanamido]-3-phenylpropanoic acid

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C15H21NO4/c1-10(2)13(17)14(18)16(3)12(15(19)20)9-11-7-5-4-6-8-11/h4-8,10,12-13,17H,9H2,1-3H3,(H,19,20)/t12-,13-/m1/s1

InChI Key

AFSFYXHJJVYLOJ-CHWSQXEVSA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Isaria japonica	NPAtlas	11988860

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as phenylalanine and derivatives. Phenylalanine and derivatives are compounds containing phenylalanine or a derivative thereof resulting from reaction of phenylalanine at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

Phenylalanine and derivatives

Alternative Parents

Substituents

Phenylalanine or derivatives
N-acyl-alpha-amino acid
N-acyl-alpha amino acid or derivatives
3-phenylpropanoic-acid
Amphetamine or derivatives
Monocyclic benzene moiety
N-acyl-amine
Benzenoid
Tertiary carboxylic acid amide
Carboxamide group
Secondary alcohol
Monocarboxylic acid or derivatives
Carboxylic acid
Organic nitrogen compound
Hydrocarbon derivative
Organic oxide
Alcohol
Carbonyl group
Organic oxygen compound
Organonitrogen compound
Organooxygen compound
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	1.37	ALOGPS
logP	1.76	ChemAxon
logS	-2.3	ALOGPS
pKa (Strongest Acidic)	4.11	ChemAxon
pKa (Strongest Basic)	-3.7	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	77.84 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	74.65 m³·mol⁻¹	ChemAxon
Polarizability	28.95 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

NPAtlas ID

NPA019709

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

9406344

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

11231296

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Showing NP-Card for (3R,6R)-N-methyl-N-(1-hydroxy-2-methylpropyl)-phenylalanine (NP0004142)

MOL for NP0004142 ((3R,6R)-N-methyl-N-(1-hydroxy-2-methylpropyl)-phenylalanine)

3D MOL for NP0004142 ((3R,6R)-N-methyl-N-(1-hydroxy-2-methylpropyl)-phenylalanine)

3D SDF for NP0004142 ((3R,6R)-N-methyl-N-(1-hydroxy-2-methylpropyl)-phenylalanine)

3D-SDF for NP0004142 ((3R,6R)-N-methyl-N-(1-hydroxy-2-methylpropyl)-phenylalanine)

PDB for NP0004142 ((3R,6R)-N-methyl-N-(1-hydroxy-2-methylpropyl)-phenylalanine)

3D PDB for NP0004142 ((3R,6R)-N-methyl-N-(1-hydroxy-2-methylpropyl)-phenylalanine)

SMILES for NP0004142 ((3R,6R)-N-methyl-N-(1-hydroxy-2-methylpropyl)-phenylalanine)

INCHI for NP0004142 ((3R,6R)-N-methyl-N-(1-hydroxy-2-methylpropyl)-phenylalanine)

Structure for NP0004142 ((3R,6R)-N-methyl-N-(1-hydroxy-2-methylpropyl)-phenylalanine)

3D Structure for NP0004142 ((3R,6R)-N-methyl-N-(1-hydroxy-2-methylpropyl)-phenylalanine)