NP-MRD: Showing NP-Card for Coclaurine (NP0047710)

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Record Information

Version

2.0

Created at

2022-03-17 20:44:40 UTC

Updated at

2022-03-17 20:44:40 UTC

NP-MRD ID

NP0047710

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Coclaurine

Description

Coclaurine is found in Cocculus hirsutus, Cocculus laurifolius, Cocculus orbiculatus, Coptis japonica, Cryptocarya concinna, Fumaria parviflora, Fumaria vaillantii, Machilus japonica, Macleaya cordata, Magnolia salicifolia, Mezilaurus synandra, Nelumbo nucifera, Pachygone ovata, Roemeria refracta, Stephania excentrica, Stephania pierrei, Xylopia parviflora and Ziziphus jujuba.

Structure

MOL SDF PDB SMILES InChI


  Mrv0541 02241218522D          

 21 23  0  0  0  0            999 V2000
   -1.7734    1.6909    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0309    2.1034    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3709    1.6909    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4534    0.8659    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1133    0.4541    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7734    0.8659    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5159    0.4541    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3716    2.1034    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1133    1.6084    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1133    0.7834    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4534    0.3716    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3716   -0.4534    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2883   -0.8659    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8559    2.0208    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.5159    1.6084    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5159    0.7834    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8559    0.3716    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8559   -0.4534    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1133   -0.8659    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1133   -1.6909    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8559   -2.1034    0.0000 C   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
 20 21  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0047710

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC2=C(C=C1O)C(CC1=CC=C(O)C=C1)NCC2

> <INCHI_IDENTIFIER>
InChI=1S/C17H19NO3/c1-21-17-9-12-6-7-18-15(14(12)10-16(17)20)8-11-2-4-13(19)5-3-11/h2-5,9-10,15,18-20H,6-8H2,1H3

> <INCHI_KEY>
LVVKXRQZSRUVPY-UHFFFAOYSA-N

> <FORMULA>
C17H19NO3

> <MOLECULAR_WEIGHT>
285.3377

> <EXACT_MASS>
285.136493479

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
31.313315221840032

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
1-[(4-hydroxyphenyl)methyl]-6-methoxy-1,2,3,4-tetrahydroisoquinolin-7-ol

> <ALOGPS_LOGP>
2.20

> <JCHEM_LOGP>
2.5109961516827504

> <ALOGPS_LOGS>
-3.37

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
10.510331536726953

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.916751037094782

> <JCHEM_PKA_STRONGEST_BASIC>
8.91020233984593

> <JCHEM_POLAR_SURFACE_AREA>
61.72

> <JCHEM_REFRACTIVITY>
82.07840000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.23e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(RS)-coclaurine

> <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      -3.310   3.156   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.924   3.926   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -0.692   3.156   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -0.846   1.616   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -2.078   0.848   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -3.310   1.616   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      -4.696   0.848   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       0.694   3.926   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.078   3.002   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.078   1.462   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.846   0.694   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       0.694  -0.846   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0      -0.538  -1.616   0.000  0.00  0.00           O+0
HETATM   14  N   UNK     0       3.464   3.772   0.000  0.00  0.00           N+0
HETATM   15  C   UNK     0       4.696   3.002   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       4.696   1.462   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       3.464   0.694   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       3.464  -0.846   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       2.078  -1.616   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       2.078  -3.156   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       3.464  -3.926   0.000  0.00  0.00           C+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   21                                                       
CONECT   21   20                                                            
MASTER        0    0    0    0    0    0    0    0   21    0   46    0
END

View in JSmol

Synonyms

Value	Source
(R,S)-Coclaurine	ChEBI
6-Methoxy-7-hydroxy-1-[(4-hydroxyphenyl)methyl]-1,2,3,4-tetrahydroisoquinoline	ChEBI
DL-Coclaurine	Kegg
Machiline	Kegg
Coclaurine	ChEBI

Chemical Formula

C₁₇H₁₉NO₃

Average Mass

285.3377 Da

Monoisotopic Mass

285.13649 Da

IUPAC Name

1-[(4-hydroxyphenyl)methyl]-6-methoxy-1,2,3,4-tetrahydroisoquinolin-7-ol

Traditional Name

(RS)-coclaurine

CAS Registry Number

2196-60-3

SMILES

COC1=CC2=C(C=C1O)C(CC1=CC=C(O)C=C1)NCC2

InChI Identifier

InChI=1S/C17H19NO3/c1-21-17-9-12-6-7-18-15(14(12)10-16(17)20)8-11-2-4-13(19)5-3-11/h2-5,9-10,15,18-20H,6-8H2,1H3

InChI Key

LVVKXRQZSRUVPY-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Annona muricata	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Annona reticulata	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Cocculus hirsutus	LOTUS Database	35616633
Cocculus laurifolius	LOTUS Database	35616633
Cocculus orbiculatus	LOTUS Database	35616633
Coptis japonica	LOTUS Database	35616633
Cryptocarya concinna	LOTUS Database	35616633
Fumaria parviflora	LOTUS Database	35616633
Fumaria vaillantii	LOTUS Database	35616633
Machilus japonica	Plant	KNApSAcK
Macleaya cordata	LOTUS Database	35616633
Magnolia salicifolia	LOTUS Database	35616633
Mezilaurus synandra	LOTUS Database	35616633
Nelumbo nucifera	LOTUS Database	35616633
Pachygone ovata	LOTUS Database	35616633
Roemeria refracta	LOTUS Database	35616633
Stephania excentrica	LOTUS Database	35616633
Stephania pierrei	LOTUS Database	35616633
Xylopia parviflora	LOTUS Database	35616633
Ziziphus jujuba	LOTUS Database	35616633

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
Anisole
Alkyl aryl ether
1-hydroxy-2-unsubstituted benzenoid
Phenol
Aralkylamine
Benzenoid
Monocyclic benzene moiety
Secondary amine
Ether
Secondary aliphatic amine
Azacycle
Organic oxygen compound
Organic nitrogen compound
Organooxygen compound
Organonitrogen compound
Amine
Hydrocarbon derivative
Organopnictogen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

coclaurine (CHEBI:18417 )

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	2.2	ALOGPS
logP	2.51	ChemAxon
logS	-3.4	ALOGPS
pKa (Strongest Acidic)	9.92	ChemAxon
pKa (Strongest Basic)	8.91	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	61.72 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	82.08 m³·mol⁻¹	ChemAxon
Polarizability	31.31 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

FDB011812

KNApSAcK ID

C00047850

Chemspider ID

Not Available

KEGG Compound ID

C06348

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Coclaurine

METLIN ID

Not Available

PubChem Compound

281691

PDB ID

Not Available

ChEBI ID

18417

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Coclaurine (NP0047710)

MOL for NP0047710 (Coclaurine)

3D MOL for NP0047710 (Coclaurine)

3D SDF for NP0047710 (Coclaurine)

3D-SDF for NP0047710 (Coclaurine)

PDB for NP0047710 (Coclaurine)

3D PDB for NP0047710 (Coclaurine)

SMILES for NP0047710 (Coclaurine)

INCHI for NP0047710 (Coclaurine)

Structure for NP0047710 (Coclaurine)

3D Structure for NP0047710 (Coclaurine)