NP-MRD: Showing NP-Card for ambroxol (NP0273705)

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Record Information

Version

2.0

Created at

2022-09-08 20:50:05 UTC

Updated at

2022-09-08 20:50:05 UTC

NP-MRD ID

NP0273705

Secondary Accession Numbers

None

Natural Product Identification

Common Name

ambroxol

Description

4-{[(2-Amino-3,5-dibromophenyl)methyl]amino}cyclohexan-1-ol belongs to the class of organic compounds known as phenylmethylamines. Phenylmethylamines are compounds containing a phenylmethtylamine moiety, which consists of a phenyl group substituted by an methanamine. ambroxol is found in Justicia adhatoda. 4-{[(2-Amino-3,5-dibromophenyl)methyl]amino}cyclohexan-1-ol is a very strong basic compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 36 37  0  0  0  0  0  0  0  0999 V2000
    2.2402    2.1854   -0.5848 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.0296    0.9989   -0.4085 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3537    1.0147   -0.1076 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2136    2.7046    0.1500 Br  0  0  0  0  0  0  0  0  0  0  0  0
    5.0400   -0.1766    0.0659 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4083   -1.3931   -0.0635 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4250   -3.0516    0.0862 Br  0  0  0  0  0  0  0  0  0  0  0  0
    3.0546   -1.4203   -0.3644 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4120   -0.2064   -0.5271 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9799   -0.2753   -1.0551 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1538   -0.4696    0.0546 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2045   -0.8241   -0.1214 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.9074    0.0408   -1.1367 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8403    1.0052   -0.4722 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9638    0.2544    0.1961 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.6205    1.1426    1.0378 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3883   -0.8784    1.0066 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9252   -0.6649    1.2676 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5363    3.0352   -0.0636 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4140    2.2145   -1.1779 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0604   -0.1529    0.3030 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6009   -2.3807   -0.4366 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9672   -1.2527   -1.7100 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7394    0.4977   -1.7478 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3571    0.0706    0.9181 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3917   -1.8642   -0.4029 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2340    0.5749   -1.8173 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5236   -0.6033   -1.8226 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3444    1.5888   -1.3213 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3258    1.7060    0.2094 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6233   -0.1506   -0.5906 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0752    0.7225    1.7878 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4546   -1.8540    0.4579 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9655   -0.9789    1.9656 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6619    0.3285    1.6174 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5356   -1.4875    1.8707 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  3  5  1  0
  5  6  2  0
  6  7  1  0
  6  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 15 17  1  0
 17 18  1  0
  9  2  1  0
 18 12  1  0
  1 19  1  0
  1 20  1  0
  5 21  1  0
  8 22  1  0
 10 23  1  0
 10 24  1  0
 11 25  1  0
 12 26  1  6
 13 27  1  0
 13 28  1  0
 14 29  1  0
 14 30  1  0
 15 31  1  6
 16 32  1  0
 17 33  1  0
 17 34  1  0
 18 35  1  0
 18 36  1  0
M  END


  Mrv1652306031607012D          

 18 19  0  0  0  0            999 V2000
    0.7145   -3.7125    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
   -0.7145   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -6.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -7.8375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -7.4250    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
    0.0000   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -7.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -6.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -7.8375    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -7.8375    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -6.1875    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -4.9500    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  3  1  1  0  0  0  0
  4  2  1  0  0  0  0
  8  5  2  0  0  0  0
  8  7  1  0  0  0  0
  9  5  1  0  0  0  0
  9  6  2  0  0  0  0
 10  1  1  0  0  0  0
 10  2  1  0  0  0  0
 11  3  1  0  0  0  0
 11  4  1  0  0  0  0
 12  6  1  0  0  0  0
 13  8  1  0  0  0  0
 13 12  2  0  0  0  0
 14  9  1  0  0  0  0
 15 12  1  0  0  0  0
 16 13  1  0  0  0  0
 17  7  1  0  0  0  0
 17 10  1  0  0  0  0
 18 11  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0273705

> <DATABASE_NAME>
NP-MRD

> <SMILES>
NC1=C(Br)C=C(Br)C=C1CNC1CCC(O)CC1

> <INCHI_IDENTIFIER>
InChI=1S/C13H18Br2N2O/c14-9-5-8(13(16)12(15)6-9)7-17-10-1-3-11(18)4-2-10/h5-6,10-11,17-18H,1-4,7,16H2

> <INCHI_KEY>
JBDGDEWWOUBZPM-UHFFFAOYSA-N

> <FORMULA>
C13H18Br2N2O

> <MOLECULAR_WEIGHT>
378.108

> <EXACT_MASS>
375.978589

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
36

> <JCHEM_AVERAGE_POLARIZABILITY>
32.774684170652506

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
4-{[(2-amino-3,5-dibromophenyl)methyl]amino}cyclohexan-1-ol

> <ALOGPS_LOGP>
3.72

> <JCHEM_LOGP>
2.6527259470000004

> <ALOGPS_LOGS>
-4.31

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
19.893025842966654

> <JCHEM_PKA_STRONGEST_ACIDIC>
15.25660511777695

> <JCHEM_PKA_STRONGEST_BASIC>
9.011035150439888

> <JCHEM_POLAR_SURFACE_AREA>
58.28

> <JCHEM_REFRACTIVITY>
81.9357

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.85e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
ambroβ

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 03-JUN-16   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   03-JUN-16         0                                  
HETATM    1  C   UNK     0       1.334  -6.930   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.334  -6.930   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.334  -5.390   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -1.334  -5.390   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.000 -12.320   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -1.334 -14.630   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -1.334 -10.010   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -1.334 -11.550   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.000 -13.860   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.000  -7.700   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.000  -4.620   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -2.667 -13.860   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -2.667 -12.320   0.000  0.00  0.00           C+0
HETATM   14 Br   UNK     0       1.334 -14.630   0.000  0.00  0.00          Br+0
HETATM   15 Br   UNK     0      -4.001 -14.630   0.000  0.00  0.00          Br+0
HETATM   16  N   UNK     0      -4.001 -11.550   0.000  0.00  0.00           N+0
HETATM   17  N   UNK     0       0.000  -9.240   0.000  0.00  0.00           N+0
HETATM   18  O   UNK     0       0.000  -3.080   0.000  0.00  0.00           O+0
CONECT    1    3   10                                                       
CONECT    2    4   10                                                       
CONECT    3    1   11                                                       
CONECT    4    2   11                                                       
CONECT    5    8    9                                                       
CONECT    6    9   12                                                       
CONECT    7    8   17                                                       
CONECT    8    5    7   13                                                  
CONECT    9    5    6   14                                                  
CONECT   10    1    2   17                                                  
CONECT   11    3    4   18                                                  
CONECT   12    6   13   15                                                  
CONECT   13    8   12   16                                                  
CONECT   14    9                                                            
CONECT   15   12                                                            
CONECT   16   13                                                            
CONECT   17    7   10                                                       
CONECT   18   11                                                            
MASTER        0    0    0    0    0    0    0    0   18    0   38    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₃H₁₈Br₂N₂O

Average Mass

378.1080 Da

Monoisotopic Mass

375.97859 Da

IUPAC Name

4-{[(2-amino-3,5-dibromophenyl)methyl]amino}cyclohexan-1-ol

Traditional Name

ambroβ

CAS Registry Number

Not Available

SMILES

NC1=C(Br)C=C(Br)C=C1CNC1CCC(O)CC1

InChI Identifier

InChI=1S/C13H18Br2N2O/c14-9-5-8(13(16)12(15)6-9)7-17-10-1-3-11(18)4-2-10/h5-6,10-11,17-18H,1-4,7,16H2

InChI Key

JBDGDEWWOUBZPM-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
Adhatoda vasica	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as phenylmethylamines. Phenylmethylamines are compounds containing a phenylmethtylamine moiety, which consists of a phenyl group substituted by an methanamine.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Phenylmethylamines

Direct Parent

Phenylmethylamines

Alternative Parents

Substituents

Benzylamine
Aniline or substituted anilines
2-bromoaniline
Phenylmethylamine
Bromobenzene
Aralkylamine
Cyclohexanol
Cyclohexylamine
Halobenzene
Aryl bromide
Aryl halide
Cyclic alcohol
Secondary alcohol
Secondary amine
Secondary aliphatic amine
Organonitrogen compound
Amine
Organooxygen compound
Primary amine
Alcohol
Hydrocarbon derivative
Organopnictogen compound
Organic oxygen compound
Organic nitrogen compound
Organohalogen compound
Organobromide
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	3.72	ALOGPS
logP	2.65	ChemAxon
logS	-4.3	ALOGPS
pKa (Strongest Acidic)	15.26	ChemAxon
pKa (Strongest Basic)	9.01	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	58.28 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	81.94 m³·mol⁻¹	ChemAxon
Polarizability	32.77 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

2132

PDB ID

Not Available

ChEBI ID

92994

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for ambroxol (NP0273705)

MOL for NP0273705 (ambroxol)

3D MOL for NP0273705 (ambroxol)

3D SDF for NP0273705 (ambroxol)

3D-SDF for NP0273705 (ambroxol)

PDB for NP0273705 (ambroxol)

3D PDB for NP0273705 (ambroxol)

SMILES for NP0273705 (ambroxol)

INCHI for NP0273705 (ambroxol)

Structure for NP0273705 (ambroxol)

3D Structure for NP0273705 (ambroxol)