NP-MRD: Showing NP-Card for Higenamine HCl (NP0138233)

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Record Information

Version

1.0

Created at

2022-05-31 17:16:45 UTC

Updated at

2022-05-31 17:16:45 UTC

NP-MRD ID

NP0138233

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Higenamine HCl

Description

Higenamine hydrochloride belongs to the class of organic compounds known as benzylisoquinolines. These are organic compounds containing an isoquinoline to which a benzyl group is attached. It was first documented in 2011 (PMID: 21393074). Based on a literature review very few articles have been published on Higenamine hydrochloride (PMID: 30648306).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 39 40  0  0  0  0  0  0  0  0999 V2000
    0.6901    0.0000    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    6.2486    0.3265    0.4039 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9050    0.2373    0.0548 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2415   -0.9914    0.0278 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8990   -1.0290   -0.3274 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2354    0.1339   -0.6480 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7930    0.0133   -1.0197 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1011    0.1310    0.1680 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.2178   -0.8985    1.1255 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8443   -1.4873    1.8346 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9103   -0.4425    2.1522 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4652   -0.0874    0.8001 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7802   -0.0320    0.4924 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2017    0.2937   -0.7815 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5470    0.3512   -1.0989 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3018    0.5710   -1.7742 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6953    0.9049   -3.0779 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9429    0.5067   -1.4288 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5171    0.1882   -0.1808 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9077    1.3132   -0.6125 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2294    1.3947   -0.2683 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6901    0.0000    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4471    0.4627    1.3921 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8101   -1.8600    0.2868 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4277   -2.0076   -0.3335 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6336   -0.9285   -1.5717 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5634    0.8563   -1.7390 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1395    1.1064    0.6879 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0650   -0.6489    1.6710 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4651   -1.8322    2.8391 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3551   -2.3323    1.3275 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3823    0.4468    2.5243 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6854   -0.8247    2.8257 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5133   -0.2529    1.2819 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2113    0.1462   -0.3652 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6830    0.9409   -3.2880 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2810    0.7350   -2.2630 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3896    2.2222   -0.8629 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7299    2.3731   -0.2543 H   0  0  0  0  0  0  0  0  0  0  0  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  1  0
 14 16  2  0
 16 17  1  0
 16 18  1  0
 18 19  2  0
  6 20  1  0
 20 21  2  0
 21  3  1  0
 19  8  1  0
 19 12  1  0
  1 22  1  0
  2 23  1  0
  4 24  1  0
  5 25  1  0
  7 26  1  0
  7 27  1  0
  8 28  1  1
  9 29  1  0
 10 30  1  0
 10 31  1  0
 11 32  1  0
 11 33  1  0
 13 34  1  0
 15 35  1  0
 17 36  1  0
 18 37  1  0
 20 38  1  0
 21 39  1  0
M  END


  Mrv1652305312219162D          

 21 22  0  0  0  0            999 V2000
    0.0000    0.0000    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    1.8857   -2.3100    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6002   -1.8975    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6002   -1.0725    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3147   -0.6600    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0291   -1.0725    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7436   -0.6600    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7436    0.1650    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0291    0.5775    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.0291    1.4025    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7436    1.8150    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4581    1.4025    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1725    1.8150    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8870    1.4025    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6015    1.8150    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.8870    0.5775    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6015    0.1650    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1725    0.1650    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4581    0.5775    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0291   -1.8975    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3147   -2.3100    0.0000 C   0  0  0  0  0  0  0  0  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  1  0  0  0  0
  8  9  1  0  0  0  0
  9 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  1  0  0  0  0
 14 16  2  0  0  0  0
 16 17  1  0  0  0  0
 16 18  1  0  0  0  0
 18 19  2  0  0  0  0
  8 19  1  0  0  0  0
 12 19  1  0  0  0  0
  6 20  1  0  0  0  0
 20 21  2  0  0  0  0
  3 21  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0138233

> <DATABASE_NAME>
NP-MRD

> <SMILES>
Cl.OC1=CC=C(CC2NCCC3=CC(O)=C(O)C=C23)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C16H17NO3.ClH/c18-12-3-1-10(2-4-12)7-14-13-9-16(20)15(19)8-11(13)5-6-17-14;/h1-4,8-9,14,17-20H,5-7H2;1H

> <INCHI_KEY>
SWWQQSDRUYSMAR-UHFFFAOYSA-N

> <FORMULA>
C16H18ClNO3

> <MOLECULAR_WEIGHT>
307.77

> <EXACT_MASS>
307.0975211

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
39

> <JCHEM_AVERAGE_POLARIZABILITY>
29.22031365719127

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
1-[(4-hydroxyphenyl)methyl]-1,2,3,4-tetrahydroisoquinoline-6,7-diol hydrochloride

> <JCHEM_LOGP>
2.358229571055738

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
10.311471952765332

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.5635166213882

> <JCHEM_PKA_STRONGEST_BASIC>
9.466291658358584

> <JCHEM_POLAR_SURFACE_AREA>
72.72

> <JCHEM_REFRACTIVITY>
77.5961

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
higenamine hydrochloride

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 31-MAY-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   31-MAY-22         0                                  
HETATM    1 Cl   UNK     0       0.000   0.000   0.000  0.00  0.00          Cl+0
HETATM    2  O   UNK     0       3.520  -4.312   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       4.854  -3.542   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       4.854  -2.002   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       6.187  -1.232   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       7.521  -2.002   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       8.855  -1.232   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       8.855   0.308   0.000  0.00  0.00           C+0
HETATM    9  N   UNK     0       7.521   1.078   0.000  0.00  0.00           N+0
HETATM   10  C   UNK     0       7.521   2.618   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       8.855   3.388   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      10.188   2.618   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      11.522   3.388   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      12.856   2.618   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      14.189   3.388   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0      12.856   1.078   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      14.189   0.308   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0      11.522   0.308   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      10.188   1.078   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       7.521  -3.542   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       6.187  -4.312   0.000  0.00  0.00           C+0
CONECT    2    3                                                            
CONECT    3    2    4   21                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7   20                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   19                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13   19                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16   19                                                       
CONECT   19   18    8   12                                                  
CONECT   20    6   21                                                       
CONECT   21   20    3                                                       
MASTER        0    0    0    0    0    0    0    0   21    0   44    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₆H₁₈ClNO₃

Average Mass

307.7700 Da

Monoisotopic Mass

307.09752 Da

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

11041-94-4

SMILES

Cl.OC1=CC=C(CC2NCCC3=CC(O)=C(O)C=C23)C=C1

InChI Identifier

InChI=1S/C16H17NO3.ClH/c18-12-3-1-10(2-4-12)7-14-13-9-16(20)15(19)8-11(13)5-6-17-14;/h1-4,8-9,14,17-20H,5-7H2;1H

InChI Key

SWWQQSDRUYSMAR-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

Not Available

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as benzylisoquinolines. These are organic compounds containing an isoquinoline to which a benzyl group is attached.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Isoquinolines and derivatives

Sub Class

Benzylisoquinolines

Direct Parent

Benzylisoquinolines

Alternative Parents

Substituents

Benzylisoquinoline
Tetrahydroisoquinoline
1-hydroxy-2-unsubstituted benzenoid
Phenol
Aralkylamine
Monocyclic benzene moiety
Benzenoid
Secondary aliphatic amine
Secondary amine
Azacycle
Organopnictogen compound
Organooxygen compound
Organonitrogen compound
Amine
Organic oxygen compound
Hydrocarbon derivative
Organic nitrogen compound
Hydrochloride
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

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

145392

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

165901

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Zhang N, Qu K, Wang M, Yin Q, Wang W, Xue L, Fu H, Zhu H, Li Z: Identification of higenamine as a novel alpha1 -adrenergic receptor antagonist. Phytother Res. 2019 Mar;33(3):708-717. doi: 10.1002/ptr.6261. Epub 2019 Jan 15. [PubMed:30648306 ]
Feng S, Hu P, Jiang J: Determination of higenamine in human plasma and urine using liquid chromatography coupled to positive electrospray ionization tandem mass spectrometry. J Chromatogr B Analyt Technol Biomed Life Sci. 2011 Apr 1;879(11-12):763-8. doi: 10.1016/j.jchromb.2011.02.019. Epub 2011 Feb 24. [PubMed:21393074 ]

Showing NP-Card for Higenamine HCl (NP0138233)

MOL for NP0138233 (Higenamine HCl)

3D MOL for NP0138233 (Higenamine HCl)

3D SDF for NP0138233 (Higenamine HCl)

3D-SDF for NP0138233 (Higenamine HCl)

PDB for NP0138233 (Higenamine HCl)

3D PDB for NP0138233 (Higenamine HCl)

SMILES for NP0138233 (Higenamine HCl)

INCHI for NP0138233 (Higenamine HCl)

Structure for NP0138233 (Higenamine HCl)

3D Structure for NP0138233 (Higenamine HCl)