NP-MRD: Showing NP-Card for 6-hydroxy-8-methyl-8-azabicyclo[3.2.1]octan-3-yl 2-hydroxy-3-phenylpropanoate (NP0319154)

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Record Information

Version

2.0

Created at

2022-09-11 20:02:53 UTC

Updated at

2022-09-11 20:02:54 UTC

NP-MRD ID

NP0319154

Secondary Accession Numbers

None

Natural Product Identification

Common Name

6-hydroxy-8-methyl-8-azabicyclo[3.2.1]octan-3-yl 2-hydroxy-3-phenylpropanoate

Description

6-Hydroxy-8-methyl-8-azabicyclo[3.2.1]Octan-3-yl 2-hydroxy-3-phenylpropanoate belongs to the class of organic compounds known as tropane alkaloids. These are organic compounds containing the nitrogenous bicyclic alkaloid parent N-Methyl-8-azabicyclo[3.2.1]Octane. 6-hydroxy-8-methyl-8-azabicyclo[3.2.1]octan-3-yl 2-hydroxy-3-phenylpropanoate is found in Hyoscyamus albus. Based on a literature review very few articles have been published on 6-hydroxy-8-methyl-8-azabicyclo[3.2.1]Octan-3-yl 2-hydroxy-3-phenylpropanoate.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652309112222022D          

 22 24  0  0  0  0            999 V2000
   -0.5712    0.2566    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1433   -0.1559    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1194   -1.0744    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6689   -1.3176    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3505   -0.8529    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0650   -1.2654    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7795   -0.8529    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7795   -0.0279    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4940   -1.2654    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4940   -2.0904    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2084   -0.8529    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9229   -1.2654    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6374   -0.8529    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3518   -1.2654    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3518   -2.0904    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6374   -2.5029    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9229   -2.0904    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4122   -0.0302    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8074    0.5310    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0084    0.4080    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4731    1.0897    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4209   -0.3064    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  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  7  9  1  0  0  0  0
  9 10  1  0  0  0  0
  9 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
 12 17  1  0  0  0  0
  5 18  1  0  0  0  0
 18 19  1  0  0  0  0
  2 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 20 22  1  0  0  0  0
  3 22  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0319154

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CN1C2CC(O)C1CC(C2)OC(=O)C(O)CC1=CC=CC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C17H23NO4/c1-18-12-8-13(10-14(18)15(19)9-12)22-17(21)16(20)7-11-5-3-2-4-6-11/h2-6,12-16,19-20H,7-10H2,1H3

> <INCHI_KEY>
HJHAFGCQRMACPE-UHFFFAOYSA-N

> <FORMULA>
C17H23NO4

> <MOLECULAR_WEIGHT>
305.374

> <EXACT_MASS>
305.162708225

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
45

> <JCHEM_AVERAGE_POLARIZABILITY>
33.14181427332742

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
6-hydroxy-8-methyl-8-azabicyclo[3.2.1]octan-3-yl 2-hydroxy-3-phenylpropanoate

> <JCHEM_LOGP>
0.7348310263333326

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
14.546378198315505

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.609697669605197

> <JCHEM_PKA_STRONGEST_BASIC>
8.842513941474477

> <JCHEM_POLAR_SURFACE_AREA>
70.0

> <JCHEM_REFRACTIVITY>
81.87830000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
6-hydroxy-8-methyl-8-azabicyclo[3.2.1]octan-3-yl 2-hydroxy-3-phenylpropanoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 11-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   11-SEP-22         0                                  
HETATM    1  C   UNK     0      -1.066   0.479   0.000  0.00  0.00           C+0
HETATM    2  N   UNK     0       0.268  -0.291   0.000  0.00  0.00           N+0
HETATM    3  C   UNK     0      -0.223  -2.006   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.249  -2.460   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.521  -1.592   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       3.855  -2.362   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       5.188  -1.592   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       5.188  -0.052   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       6.522  -2.362   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       6.522  -3.902   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       7.856  -1.592   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       9.189  -2.362   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      10.523  -1.592   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      11.857  -2.362   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      11.857  -3.902   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      10.523  -4.672   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       9.189  -3.902   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       2.636  -0.056   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       1.507   0.991   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -0.016   0.762   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      -0.883   2.034   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0      -0.786  -0.572   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   19                                                  
CONECT    3    2    4   22                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6   18                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12                                                       
CONECT   12   11   13   17                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   12                                                       
CONECT   18    5   19                                                       
CONECT   19   18    2   20                                                  
CONECT   20   19   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20    3                                                       
MASTER        0    0    0    0    0    0    0    0   22    0   48    0
END

View in JSmol

Synonyms

Value	Source
6-Hydroxy-8-methyl-8-azabicyclo[3.2.1]octan-3-yl 2-hydroxy-3-phenylpropanoic acid	Generator

Chemical Formula

C₁₇H₂₃NO₄

Average Mass

305.3740 Da

Monoisotopic Mass

305.16271 Da

IUPAC Name

6-hydroxy-8-methyl-8-azabicyclo[3.2.1]octan-3-yl 2-hydroxy-3-phenylpropanoate

Traditional Name

6-hydroxy-8-methyl-8-azabicyclo[3.2.1]octan-3-yl 2-hydroxy-3-phenylpropanoate

CAS Registry Number

Not Available

SMILES

CN1C2CC(O)C1CC(C2)OC(=O)C(O)CC1=CC=CC=C1

InChI Identifier

InChI=1S/C17H23NO4/c1-18-12-8-13(10-14(18)15(19)9-12)22-17(21)16(20)7-11-5-3-2-4-6-11/h2-6,12-16,19-20H,7-10H2,1H3

InChI Key

HJHAFGCQRMACPE-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Hyoscyamus albus	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as tropane alkaloids. These are organic compounds containing the nitrogenous bicyclic alkaloid parent N-Methyl-8-azabicyclo[3.2.1]Octane.

Kingdom

Organic compounds

Super Class

Alkaloids and derivatives

Class

Tropane alkaloids

Sub Class

Not Available

Direct Parent

Tropane alkaloids

Alternative Parents

Substituents

Tropane alkaloid
Fatty acid ester
Monocyclic benzene moiety
Fatty acyl
Piperidine
Benzenoid
N-alkylpyrrolidine
Cyclic alcohol
Pyrrolidine
1,2-aminoalcohol
Amino acid or derivatives
Carboxylic acid ester
Tertiary aliphatic amine
Tertiary amine
Secondary alcohol
Carboxylic acid derivative
Azacycle
Monocarboxylic acid or derivatives
Organoheterocyclic compound
Alcohol
Hydrocarbon derivative
Organic oxide
Organic nitrogen compound
Carbonyl group
Organopnictogen compound
Amine
Organonitrogen compound
Organooxygen compound
Organic oxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic 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	0.73	ChemAxon
pKa (Strongest Acidic)	12.61	ChemAxon
pKa (Strongest Basic)	8.84	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	70 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	81.88 m³·mol⁻¹	ChemAxon
Polarizability	33.14 Å³	ChemAxon
Number of Rings	3	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

91700477

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 6-hydroxy-8-methyl-8-azabicyclo[3.2.1]octan-3-yl 2-hydroxy-3-phenylpropanoate (NP0319154)

MOL for NP0319154 (6-hydroxy-8-methyl-8-azabicyclo[3.2.1]octan-3-yl 2-hydroxy-3-phenylpropanoate)

3D MOL for NP0319154 (6-hydroxy-8-methyl-8-azabicyclo[3.2.1]octan-3-yl 2-hydroxy-3-phenylpropanoate)

3D SDF for NP0319154 (6-hydroxy-8-methyl-8-azabicyclo[3.2.1]octan-3-yl 2-hydroxy-3-phenylpropanoate)

3D-SDF for NP0319154 (6-hydroxy-8-methyl-8-azabicyclo[3.2.1]octan-3-yl 2-hydroxy-3-phenylpropanoate)

PDB for NP0319154 (6-hydroxy-8-methyl-8-azabicyclo[3.2.1]octan-3-yl 2-hydroxy-3-phenylpropanoate)

3D PDB for NP0319154 (6-hydroxy-8-methyl-8-azabicyclo[3.2.1]octan-3-yl 2-hydroxy-3-phenylpropanoate)

SMILES for NP0319154 (6-hydroxy-8-methyl-8-azabicyclo[3.2.1]octan-3-yl 2-hydroxy-3-phenylpropanoate)

INCHI for NP0319154 (6-hydroxy-8-methyl-8-azabicyclo[3.2.1]octan-3-yl 2-hydroxy-3-phenylpropanoate)

Structure for NP0319154 (6-hydroxy-8-methyl-8-azabicyclo[3.2.1]octan-3-yl 2-hydroxy-3-phenylpropanoate)

3D Structure for NP0319154 (6-hydroxy-8-methyl-8-azabicyclo[3.2.1]octan-3-yl 2-hydroxy-3-phenylpropanoate)