NP-MRD: Showing NP-Card for (R)-Higenamine (NP0047548)

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Record Information

Version

2.0

Created at

2022-03-17 20:41:58 UTC

Updated at

2022-03-17 20:41:58 UTC

NP-MRD ID

NP0047548

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(R)-Higenamine

Description

(R)-Higenamine, also known as norcoclaurine, belongs to the class of organic compounds known as benzylisoquinolines. These are organic compounds containing an isoquinoline to which a benzyl group is attached (R)-Higenamine is a very strong basic compound (based on its pKa) (R)-Higenamine is a sweet, fruity, and milky tasting compound. Outside of the human body, (R)-Higenamine has been detected, but not quantified in, custard apples and opium poppies. This could make (R)-higenamine a potential biomarker for the consumption of these foods. (R)-Higenamine is found in Aconitum japonicum, Argemone mexicana, Asarum sieboldii, Gnetum parvifolium , Macleaya cordata, Nelumbo nucifera, Phoebe chekiangensis and Tinospora crispa . Higenamine is under investigation in clinical trial NCT01451229 (Pharmacokinetics and Pharmacodynamics of Higenamine in Chinese Healthy Subjects).

Structure

MOL SDF PDB SMILES InChI


  Mrv0541 02241214502D          

 20 22  0  0  0  0            999 V2000
   -1.7712    1.4826    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0299    1.8956    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3701    1.4826    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4527    0.6587    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1125    0.2478    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7712    0.6587    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5136    0.2478    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3711    1.8956    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1124    1.4010    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1124    0.5760    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4527    0.1652    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3711   -0.6587    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2875   -1.0706    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8548    1.8130    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.5136    1.4010    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5136    0.5760    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8548    0.1652    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8548   -0.6587    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1124   -1.0706    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1124   -1.8956    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  1  6  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  3  8  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
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  9 14  1  0  0  0  0
 10 11  1  0  0  0  0
 10 17  2  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 12 19  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  2  0  0  0  0
 19 20  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0047548

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC1=CC=C(CC2NCCC3=C2C=C(O)C(O)=C3)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C16H17NO3/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

> <INCHI_KEY>
WZRCQWQRFZITDX-UHFFFAOYSA-N

> <FORMULA>
C16H17NO3

> <MOLECULAR_WEIGHT>
271.3111

> <EXACT_MASS>
271.120843415

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
29.245963941760756

> <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

> <ALOGPS_LOGP>
1.73

> <JCHEM_LOGP>
2.2310176765251515

> <ALOGPS_LOGS>
-3.06

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
10.338482144787472

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.745574891365035

> <JCHEM_PKA_STRONGEST_BASIC>
9.547144490623493

> <JCHEM_POLAR_SURFACE_AREA>
72.72

> <JCHEM_REFRACTIVITY>
77.5961

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.36e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
higenamine

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  C   UNK     0      -3.306   2.768   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.922   3.538   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -0.691   2.768   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -0.845   1.230   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -2.077   0.463   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -3.306   1.230   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      -4.692   0.463   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       0.693   3.538   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.076   2.615   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.076   1.075   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.845   0.308   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       0.693  -1.230   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0      -0.537  -1.998   0.000  0.00  0.00           O+0
HETATM   14  N   UNK     0       3.462   3.384   0.000  0.00  0.00           N+0
HETATM   15  C   UNK     0       4.692   2.615   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       4.692   1.075   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       3.462   0.308   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       3.462  -1.230   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       2.076  -1.998   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       2.076  -3.538   0.000  0.00  0.00           O+0
CONECT    1    2    6                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4    8                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    1    5    7                                                  
CONECT    7    6                                                            
CONECT    8    3    9                                                       
CONECT    9    8   10   14                                                  
CONECT   10    9   11   17                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13   19                                                  
CONECT   13   12                                                            
CONECT   14    9   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   10   16   18                                                  
CONECT   18   17   19                                                       
CONECT   19   12   18   20                                                  
CONECT   20   19                                                            
MASTER        0    0    0    0    0    0    0    0   20    0   44    0
END

View in JSmol

Synonyms

Value	Source
(+-)-1,2,3,4-Tetrahydro-1-((4-hydroxyphenyl)methyl)-6,7-isoquinolinediol	ChEBI
(+-)-Demethylcoclaurine	ChEBI
(+-)-Norcoclaurine	ChEBI
(+-)-O-Demethylcoclaurine	ChEBI
(R,S)-Norcoclaurine	ChEBI
6,7-Dihydroxy-1-[(4-hydroxyphenyl)methyl]-1,2,3,4-tetrahydroisoquinoline	ChEBI
Higenamine	ChEBI
Norcoclaurine	ChEBI
(+)-Demethylcoclaurine	HMDB
(R)-Norcoclaurine	HMDB
Higenamine hydrobromide, (+-)-isomer	HMDB
Higenamine oxalate (1:1), (+-)-isomer	HMDB
Higenamine, tartrate (1:1), R-(r,r)-(+-)-isomer	HMDB
1-(p-Hydroxybenzyl)-6,7-dihydroxy-1,2,3,4-tetrahydroisoquinoline	HMDB
O-Demethylcoclaurine	HMDB
Higenamine hydrochloride, (S)-isomer	HMDB
1(S)-Norcoclaurine	HMDB

Chemical Formula

C₁₆H₁₇NO₃

Average Mass

271.3111 Da

Monoisotopic Mass

271.12084 Da

IUPAC Name

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

Traditional Name

higenamine

CAS Registry Number

106032-53-5

SMILES

OC1=CC=C(CC2NCCC3=C2C=C(O)C(O)=C3)C=C1

InChI Identifier

InChI=1S/C16H17NO3/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

InChI Key

WZRCQWQRFZITDX-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Aconitum japonicum	Plant	KNApSAcK
Annona reticulata	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Argemone mexicana	LOTUS Database	35616633
Asarum sieboldii	LOTUS Database	35616633
Coffea arabica L.	FooDB	Shmuel Yannai Dictionary of Food Compounds with CD-ROM: Additives, Flavors, and Ingredients. Chap...
Coffea canephora	FooDB	Shmuel Yannai Dictionary of Food Compounds with CD-ROM: Additives, Flavors, and Ingredients. Chap...
Gnetum parvifolium	Plant	KNApSAcK
Macleaya cordata	LOTUS Database	35616633
Nelumbo nucifera	LOTUS Database	35616633
Phoebe chekiangensis	LOTUS Database	35616633
Tinospora crispa	Plant	KNApSAcK

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
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

norcoclaurine (CHEBI:18418 )

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	1.73	ALOGPS
logP	2.23	ChemAxon
logS	-3.1	ALOGPS
pKa (Strongest Acidic)	8.75	ChemAxon
pKa (Strongest Basic)	9.55	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	72.72 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	77.6 m³·mol⁻¹	ChemAxon
Polarizability	29.25 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