NP-MRD: Showing NP-Card for Phyllalbine (NP0138834)

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Record Information

Version

2.0

Created at

2022-06-29 19:19:15 UTC

Updated at

2022-06-29 19:19:15 UTC

NP-MRD ID

NP0138834

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Phyllalbine

Description

Fillalbin belongs to the class of organic compounds known as m-methoxybenzoic acids and derivatives. These are benzoic acids in which the hydrogen atom at position 3 of the benzene ring is replaced by a methoxy group. Phyllalbine is found in Convolvulus subhirsutus. Fillalbin is a very strong basic compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 42 44  0  0  0  0  0  0  0  0999 V2000
    5.9068   -1.6248    0.9851 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8982   -0.6250    0.0116 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7216   -0.0576   -0.4535 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4915   -0.4544    0.0249 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3087    0.0907   -0.4180 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0247   -0.3531    0.1102 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0018   -1.2530    0.9888 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1586    0.1791   -0.3201 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4373   -0.1989    0.1437 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.0672    0.9721    0.8376 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5479    0.8697    0.9911 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.8437   -0.3767    1.8165 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8603   -1.4634    0.7484 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7472   -0.7271   -0.5777 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.3015   -0.7111   -0.9820 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2422    0.5826   -0.2323 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0846    1.5591   -1.2545 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4012    1.0728   -1.3818 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6274    1.4795   -1.8695 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8030    0.9223   -1.4144 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0461    1.3403   -1.9144 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1937   -1.4490    1.8105 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7279   -2.6480    0.5835 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9196   -1.6790    1.4772 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4373   -1.2379    0.7922 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2835   -0.9945    0.9075 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6302    1.0350    1.8675 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7963    1.9409    0.3489 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9162    1.7816    1.4697 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8613   -0.2642    2.2194 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0701   -0.5593    2.5815 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8485   -2.0043    0.7473 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0713   -2.2070    0.8883 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3458   -1.2248   -1.3632 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0011   -1.7677   -1.1722 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1401   -0.1637   -1.9219 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0827    2.0589   -1.4097 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3816    2.3834   -0.9972 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8338    1.1027   -2.2444 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4723    1.5139   -1.7423 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6929    2.2604   -2.6353 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8781    0.8997   -1.5472 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5 18  2  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
  5  6  1  0
  6  7  2  0
  6  8  1  0
  8  9  1  0
  9 15  1  0
 15 14  1  0
 14 13  1  0
 13 12  1  0
 12 11  1  0
 11 10  1  0
 11 16  1  0
 16 17  1  0
 20  3  1  0
 10  9  1  0
 16 14  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  4 25  1  0
 18 40  1  0
 19 41  1  0
 21 42  1  0
  9 26  1  1
 15 35  1  0
 15 36  1  0
 14 34  1  6
 13 32  1  0
 13 33  1  0
 12 30  1  0
 12 31  1  0
 11 29  1  1
 10 27  1  0
 10 28  1  0
 17 37  1  0
 17 38  1  0
 17 39  1  0
M  END


  Mrv1533004171502232D          

 21 23  0  0  0  0            999 V2000
    3.6130    4.9232    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0255    4.2087    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6130    3.4942    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0255    2.7798    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6130    2.0653    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7880    2.0653    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3755    2.7798    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7880    3.4942    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3755    4.2087    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0255    1.3508    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8505    1.3508    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6130    0.6363    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7880    0.6363    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4300    1.3796    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6257    1.5632    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9807    1.0488    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9807    0.2238    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6257   -0.2905    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4300   -0.1070    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3940    0.6363    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.5690    0.6363    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  2  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
  3  8  1  0  0  0  0
  8  9  1  0  0  0  0
  5 10  1  0  0  0  0
 10 11  2  0  0  0  0
 10 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 13 19  1  0  0  0  0
 18 20  1  0  0  0  0
 15 20  1  0  0  0  0
 20 21  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0138834

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC(=CC=C1O)C(=O)OC1CC2CCC(C1)N2C

> <INCHI_IDENTIFIER>
InChI=1S/C16H21NO4/c1-17-11-4-5-12(17)9-13(8-11)21-16(19)10-3-6-14(18)15(7-10)20-2/h3,6-7,11-13,18H,4-5,8-9H2,1-2H3

> <INCHI_KEY>
OZKTVDIYALBSMA-UHFFFAOYSA-N

> <FORMULA>
C16H21NO4

> <MOLECULAR_WEIGHT>
291.347

> <EXACT_MASS>
291.14705816

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
42

> <JCHEM_AVERAGE_POLARIZABILITY>
31.18114395148499

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
8-methyl-8-azabicyclo[3.2.1]octan-3-yl 4-hydroxy-3-methoxybenzoate

> <ALOGPS_LOGP>
2.29

> <JCHEM_LOGP>
1.2862617757073278

> <ALOGPS_LOGS>
-1.99

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.81356708884546

> <JCHEM_PKA_STRONGEST_BASIC>
9.536931449496413

> <JCHEM_POLAR_SURFACE_AREA>
59.00000000000001

> <JCHEM_REFRACTIVITY>
78.85990000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.98e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
phyllalbine

> <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  C   UNK     0       6.744   9.190   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       7.514   7.856   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       6.744   6.523   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       7.514   5.189   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       6.744   3.855   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       5.204   3.855   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.434   5.189   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       5.204   6.523   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       4.434   7.856   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       7.514   2.522   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       9.054   2.522   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0       6.744   1.188   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       5.204   1.188   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.536   2.575   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       3.035   2.918   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       1.831   1.958   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       1.831   0.418   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       3.035  -0.542   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       4.536  -0.200   0.000  0.00  0.00           C+0
HETATM   20  N   UNK     0       2.602   1.188   0.000  0.00  0.00           N+0
HETATM   21  C   UNK     0       1.062   1.188   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    8                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6   10                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    3    9                                                  
CONECT    9    8                                                            
CONECT   10    5   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10   13                                                       
CONECT   13   12   14   19                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16   20                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19   20                                                  
CONECT   19   18   13                                                       
CONECT   20   18   15   21                                                  
CONECT   21   20                                                            
MASTER        0    0    0    0    0    0    0    0   21    0   46    0
END

View in JSmol

Synonyms

Value	Source
8-Methyl-8-azabicyclo[3.2.1]octan-3-yl 4-hydroxy-3-methoxybenzoic acid	Generator

Chemical Formula

C₁₆H₂₁NO₄

Average Mass

291.3470 Da

Monoisotopic Mass

291.14706 Da

IUPAC Name

8-methyl-8-azabicyclo[3.2.1]octan-3-yl 4-hydroxy-3-methoxybenzoate

Traditional Name

phyllalbine

CAS Registry Number

4540-25-4

SMILES

COC1=CC(=CC=C1O)C(=O)OC1CC2CCC(C1)N2C

InChI Identifier

InChI=1S/C16H21NO4/c1-17-11-4-5-12(17)9-13(8-11)21-16(19)10-3-6-14(18)15(7-10)20-2/h3,6-7,11-13,18H,4-5,8-9H2,1-2H3

InChI Key

OZKTVDIYALBSMA-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
Convolvulus subhirsutus	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as m-methoxybenzoic acids and derivatives. These are benzoic acids in which the hydrogen atom at position 3 of the benzene ring is replaced by a methoxy group.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Benzoic acids and derivatives

Direct Parent

M-methoxybenzoic acids and derivatives

Alternative Parents

Substituents

P-hydroxybenzoic acid alkyl ester
P-hydroxybenzoic acid ester
M-methoxybenzoic acid or derivatives
Benzoate ester
Methoxyphenol
Tropane alkaloid
Phenoxy compound
Phenol ether
Anisole
Benzoyl
Methoxybenzene
Phenol
Alkyl aryl ether
1-hydroxy-2-unsubstituted benzenoid
Piperidine
N-alkylpyrrolidine
Pyrrolidine
Amino acid or derivatives
Carboxylic acid ester
Tertiary aliphatic amine
Tertiary amine
Monocarboxylic acid or derivatives
Azacycle
Ether
Carboxylic acid derivative
Organoheterocyclic compound
Organonitrogen compound
Hydrocarbon derivative
Amine
Organic oxide
Organopnictogen compound
Organooxygen compound
Organic nitrogen compound
Organic oxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

methoxybenzoic acid (CHEBI:8176 )
Tropane alkaloids (C10863 )

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	2.29	ALOGPS
logP	1.29	ChemAxon
logS	-2	ALOGPS
pKa (Strongest Acidic)	8.81	ChemAxon
pKa (Strongest Basic)	9.54	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	59 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	78.86 m³·mol⁻¹	ChemAxon
Polarizability	31.18 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

C00002298

Chemspider ID

Not Available

KEGG Compound ID

C10863

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

443007

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Phyllalbine (NP0138834)

MOL for NP0138834 (Phyllalbine)

3D MOL for NP0138834 (Phyllalbine)

3D SDF for NP0138834 (Phyllalbine)

3D-SDF for NP0138834 (Phyllalbine)

PDB for NP0138834 (Phyllalbine)

3D PDB for NP0138834 (Phyllalbine)

SMILES for NP0138834 (Phyllalbine)

INCHI for NP0138834 (Phyllalbine)

Structure for NP0138834 (Phyllalbine)

3D Structure for NP0138834 (Phyllalbine)