NP-MRD: Showing NP-Card for 2-{[(benzyloxy)(hydroxy)methylidene]amino}-3-phenylpropan-1-ol (NP0271468)

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Record Information

Version

2.0

Created at

2022-09-08 17:46:17 UTC

Updated at

2022-09-08 17:46:17 UTC

NP-MRD ID

NP0271468

Secondary Accession Numbers

None

Natural Product Identification

Common Name

2-{[(benzyloxy)(hydroxy)methylidene]amino}-3-phenylpropan-1-ol

Description

Cbz-DL-Phenylalaninol belongs to the class of organic compounds known as amphetamines and derivatives. These are organic compounds containing or derived from 1-phenylpropan-2-amine. 2-{[(benzyloxy)(hydroxy)methylidene]amino}-3-phenylpropan-1-ol is found in Fusarium sambucinum. Cbz-DL-Phenylalaninol is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 40 41  0  0  0  0  0  0  0  0999 V2000
    1.6463   -1.0029   -0.9806 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8922    0.0156   -1.0669 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5098   -0.1177   -0.9170 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0805   -1.4154   -0.6657 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.9755   -1.8604   -1.8079 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9962   -0.9473   -1.9593 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7686   -1.4785    0.6738 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9655   -0.6443    0.7888 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8292    0.6567    1.2250 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9168    1.5025    1.3605 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1666    1.0423    1.0550 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3428   -0.2391    0.6201 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2444   -1.0682    0.4914 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5182    1.2250   -1.3098 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8843    1.4112   -1.4624 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7208    1.0352   -0.3174 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2452    0.6917    0.9305 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1584    0.3585    1.9051 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5084    0.3509    1.6993 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9803    0.6952    0.4495 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1017    1.0352   -0.5544 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1220    0.7170   -0.9883 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2501   -2.1541   -0.6295 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3415   -2.8753   -1.5795 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3272   -1.9307   -2.7054 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5666   -0.0803   -2.2220 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9917   -2.5645    0.8668 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0068   -1.2055    1.4329 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8469    1.0209    1.4660 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7741    2.5166    1.7051 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0238    1.6987    1.1585 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3451   -0.5672    0.3883 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3643   -2.1051    0.1423 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3053    0.8992   -2.3653 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0580    2.5024   -1.6511 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1774    0.6996    1.0948 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7835    0.0903    2.8798 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2211    0.0811    2.4929 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0483    0.7082    0.2221 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5067    1.3028   -1.5323 H   0  0  0  0  0  0  0  0  0  0  0  0
  6  5  1  0
  5  4  1  0
  4  7  1  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
  4  3  1  0
  3  2  1  0
  2  1  2  0
  2 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 13  8  1  0
 21 16  1  0
  6 26  1  0
  5 24  1  0
  5 25  1  0
  4 23  1  1
  7 27  1  0
  7 28  1  0
  9 29  1  0
 10 30  1  0
 11 31  1  0
 12 32  1  0
 13 33  1  0
  3 22  1  0
 15 34  1  0
 15 35  1  0
 17 36  1  0
 18 37  1  0
 19 38  1  0
 20 39  1  0
 21 40  1  0
M  END


  Mrv1533004171510402D          

 21 22  0  0  0  0            999 V2000
    2.8579   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -4.1250    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -4.1250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -4.9500    0.0000 C   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
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
  5 10  1  0  0  0  0
  3 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 12 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 16 21  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0271468

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OCC(CC1=CC=CC=C1)NC(=O)OCC1=CC=CC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C17H19NO3/c19-12-16(11-14-7-3-1-4-8-14)18-17(20)21-13-15-9-5-2-6-10-15/h1-10,16,19H,11-13H2,(H,18,20)

> <INCHI_KEY>
WPOFMMJJCPZPAO-UHFFFAOYSA-N

> <FORMULA>
C17H19NO3

> <MOLECULAR_WEIGHT>
285.343

> <EXACT_MASS>
285.136493476

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
40

> <JCHEM_AVERAGE_POLARIZABILITY>
30.95237686005902

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
benzyl N-(1-hydroxy-3-phenylpropan-2-yl)carbamate

> <ALOGPS_LOGP>
2.04

> <JCHEM_LOGP>
2.9199513713333336

> <ALOGPS_LOGS>
-3.94

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
15.073961794162116

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.24231260798259

> <JCHEM_PKA_STRONGEST_BASIC>
-2.7603307779447555

> <JCHEM_POLAR_SURFACE_AREA>
58.56

> <JCHEM_REFRACTIVITY>
80.92890000000003

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.30e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
benzyl N-(1-hydroxy-3-phenylpropan-2-yl)carbamate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 17-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   17-APR-15         0                                  
HETATM    1  O   UNK     0       5.335  -4.620   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       4.001  -5.390   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       4.001  -6.930   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.667  -7.700   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.334  -6.930   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.000  -7.700   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -1.334  -6.930   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -1.334  -5.390   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.000  -4.620   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.334  -5.390   0.000  0.00  0.00           C+0
HETATM   11  N   UNK     0       5.335  -7.700   0.000  0.00  0.00           N+0
HETATM   12  C   UNK     0       6.668  -6.930   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       6.668  -5.390   0.000  0.00  0.00           O+0
HETATM   14  O   UNK     0       8.002  -7.700   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       9.336  -6.930   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      10.669  -7.700   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      12.003  -6.930   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      13.337  -7.700   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      13.337  -9.240   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      12.003 -10.010   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      10.669  -9.240   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   11                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6   10                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9    5                                                       
CONECT   11    3   12                                                       
CONECT   12   11   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17   21                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   16                                                       
MASTER        0    0    0    0    0    0    0    0   21    0   44    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₇H₁₉NO₃

Average Mass

285.3430 Da

Monoisotopic Mass

285.13649 Da

IUPAC Name

benzyl N-(1-hydroxy-3-phenylpropan-2-yl)carbamate

Traditional Name

benzyl N-(1-hydroxy-3-phenylpropan-2-yl)carbamate

CAS Registry Number

Not Available

SMILES

OCC(CC1=CC=CC=C1)NC(=O)OCC1=CC=CC=C1

InChI Identifier

InChI=1S/C17H19NO3/c19-12-16(11-14-7-3-1-4-8-14)18-17(20)21-13-15-9-5-2-6-10-15/h1-10,16,19H,11-13H2,(H,18,20)

InChI Key

WPOFMMJJCPZPAO-UHFFFAOYSA-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, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, 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
Fusarium sambucinum	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as amphetamines and derivatives. These are organic compounds containing or derived from 1-phenylpropan-2-amine.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Phenethylamines

Direct Parent

Amphetamines and derivatives

Alternative Parents

Substituents

Benzyloxycarbonyl
Amphetamine or derivatives
Carbamic acid ester
Carbonic acid derivative
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Primary alcohol
Organooxygen compound
Organonitrogen compound
Carbonyl group
Alcohol
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	2.04	ALOGPS
logP	2.92	ChemAxon
logS	-3.9	ALOGPS
pKa (Strongest Acidic)	14.24	ChemAxon
pKa (Strongest Basic)	-2.8	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	58.56 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	80.93 m³·mol⁻¹	ChemAxon
Polarizability	30.95 Å³	ChemAxon
Number of Rings	2	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

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

52361

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 2-{[(benzyloxy)(hydroxy)methylidene]amino}-3-phenylpropan-1-ol (NP0271468)

MOL for NP0271468 (2-{[(benzyloxy)(hydroxy)methylidene]amino}-3-phenylpropan-1-ol)

3D MOL for NP0271468 (2-{[(benzyloxy)(hydroxy)methylidene]amino}-3-phenylpropan-1-ol)

3D SDF for NP0271468 (2-{[(benzyloxy)(hydroxy)methylidene]amino}-3-phenylpropan-1-ol)

3D-SDF for NP0271468 (2-{[(benzyloxy)(hydroxy)methylidene]amino}-3-phenylpropan-1-ol)

PDB for NP0271468 (2-{[(benzyloxy)(hydroxy)methylidene]amino}-3-phenylpropan-1-ol)

3D PDB for NP0271468 (2-{[(benzyloxy)(hydroxy)methylidene]amino}-3-phenylpropan-1-ol)

SMILES for NP0271468 (2-{[(benzyloxy)(hydroxy)methylidene]amino}-3-phenylpropan-1-ol)

INCHI for NP0271468 (2-{[(benzyloxy)(hydroxy)methylidene]amino}-3-phenylpropan-1-ol)

Structure for NP0271468 (2-{[(benzyloxy)(hydroxy)methylidene]amino}-3-phenylpropan-1-ol)

3D Structure for NP0271468 (2-{[(benzyloxy)(hydroxy)methylidene]amino}-3-phenylpropan-1-ol)