NP-MRD: Showing NP-Card for (+,-)-reticuline (NP0266007)

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Record Information

Version

2.0

Created at

2022-09-08 10:12:07 UTC

Updated at

2022-09-08 10:12:07 UTC

NP-MRD ID

NP0266007

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(+,-)-reticuline

Description

(S)-Reticuline, also known as reticline, belongs to the class of organic compounds known as benzylisoquinolines. (+,-)-reticuline is found in Aconitum seravschanicum, Annona cherimola, Annona emarginata, Annona glabra, Annona purpurea, Annona reticulata, Argemone mexicana, Argemone platyceras, Aristolochia gigantea, Artabotrys hexapetalus, Artabotrys monteiroae, Artabotrys venustus, Berberis heteropoda, Berberis integerrima, Berberis nummularia, Berberis stolonifera, Bongardia chrysogonum, Cissampelos capensis, Clematis parviloba, Coptis japonica, Corydalis taliensis, Croton celtidifolius, Croton hemiargyreus, Cymbopetalum brasiliense, Dehaasia hainanensis, Delphinium pentagynum, Dicentra peregrina, Erythrina variegata, Fumaria capreolata, Fumaria vaillantii, Glaucium corniculatum, Glaucium fimbrilligerum, Glaucium flavum, Glossocalyx brevipes, Greenwayodendron oliveri, Guatteria juruensis, Gyrocarpus americanus, Hernandia nymphaeifolia, Hypserpa nitida, Isopyrum thalictroides, Laureliopsis philippiana, Laurobasidium lauri, Laurus nobilis, Leontice leontopetalum, Leptadenia reticulata, Lindera aggregata, Lindera glauca, Lindera megaphylla, Litsea cubeba, Litsea elliptica, Litsea lancifolia, Magnolia officinalis, Magnolia salicifolia, Miliusa velutina, Monocyclanthus vignei, Neolitsea aciculata, Neolitsea konishii, Ocotea velloziana, Pachygone ovata, Papaver somniferum, Stephania cephalantha, Stephania pierrei, Stephania venosa, Stephania viridiflavens, Thalictrum foliolosum, Uvaria dulcis and Xylopia parviflora. (+,-)-reticuline was first documented in 2004 (PMID: 15272474). These are organic compounds containing an isoquinoline to which a benzyl group is attached (S)-Reticuline is a very strong basic compound (based on its pKa) (PMID: 15036439) (PMID: 15383669) (PMID: 15874902) (PMID: 15937106).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 47 49  0  0  0  0  0  0  0  0999 V2000
   -6.8121   -1.8698   -0.8012 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0898   -1.0945    0.1428 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7931   -0.7003   -0.1057 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1153   -1.0322   -1.2834 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8175   -0.6176   -1.4930 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1750    0.1307   -0.5392 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7828    0.6324   -0.6532 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2419   -0.2759   -0.1273 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.6016    0.2811   -0.3656 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8629    1.2893   -1.2491 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1505    1.7975   -1.4558 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2965    2.8219   -2.3784 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2137    1.2815   -0.7561 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4944    1.7778   -0.9532 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.5503    1.2133   -0.2100 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9443    0.2609    0.1376 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6814   -0.2319    0.3350 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4553   -1.3110    1.3000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0301   -1.7127    1.4969 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0834   -0.6065    1.2818 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.4591    0.4527    2.1585 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8576    0.4466    0.6110 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1594    0.0506    0.8601 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8303    0.3896    2.0462 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1130   -1.2157   -1.6530 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7025   -2.3357   -0.3602 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1935   -2.6750   -1.2279 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6330   -1.6230   -2.0284 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2731   -0.8693   -2.4099 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6426    0.7873   -1.7641 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7367    1.6293   -0.1924 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2042   -1.2469   -0.6731 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0475    1.7270   -1.8192 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5440    3.2147   -2.8992 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5147    1.7191   -0.4187 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2646    1.2937    0.8637 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7038    0.1413   -0.4354 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8127   -0.1337    0.6842 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9952   -2.2168    0.8937 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9754   -1.1090    2.2634 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9267   -2.1003    2.5340 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7745   -2.5544    0.8288 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7592    1.3870    1.6656 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3067    0.1785    2.8507 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4047    0.6431    2.8614 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3948    1.0448    1.4135 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3678    0.9402    2.7561 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3 23  2  0
 23 24  1  0
 23 22  1  0
 22  6  2  0
  6  7  1  0
  7  8  1  0
  8 20  1  0
 20 21  1  0
 20 19  1  0
 19 18  1  0
 18 17  1  0
 17 16  2  0
 16 13  1  0
 13 14  1  0
 14 15  1  0
 13 11  2  0
 11 12  1  0
 11 10  1  0
 10  9  2  0
  6  5  1  0
  5  4  2  0
  4  3  1  0
  9  8  1  0
  9 17  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
 24 47  1  0
 22 46  1  0
  7 30  1  0
  7 31  1  0
  8 32  1  6
 21 43  1  0
 21 44  1  0
 21 45  1  0
 19 41  1  0
 19 42  1  0
 18 39  1  0
 18 40  1  0
 16 38  1  0
 15 35  1  0
 15 36  1  0
 15 37  1  0
 12 34  1  0
 10 33  1  0
  5 29  1  0
  4 28  1  0
M  END


  Mrv1652307152023352D          

 24 26  0  0  0  0            999 V2000
10000.075710000.0061    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.5030 9999.1791    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.507110002.4811    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9997.2235 9999.1791    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10002.934410001.6561    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9997.2235 9997.5229    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10003.650110001.2436    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9996.3698 9998.0142    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.219610001.2437    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.505110001.6561    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.790610001.2436    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.790510000.4186    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.505010000.0061    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.219610000.4187    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.6505 9999.1749    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.9359 9998.7624    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.9359 9997.9375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.6504 9997.5249    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.0760 9999.1750    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
 9999.3615 9998.7625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.3615 9997.9374    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.0760 9997.5250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.7905 9997.9374    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.7905 9998.7625    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  5  7  1  0  0  0  0
  6  8  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14  9  1  0  0  0  0
  1 12  1  0  0  0  0
 10  3  1  0  0  0  0
  9  5  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 16  4  1  0  0  0  0
 17  6  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 19 24  1  0  0  0  0
 23 24  1  0  0  0  0
 19  1  1  6  0  0  0
 24  2  1  0  0  0  0
 20 15  2  0  0  0  0
 18 21  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0266007

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=C(O)C=C(C[C@@H]2N(C)CCC3=CC(OC)=C(O)C=C23)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C19H23NO4/c1-20-7-6-13-10-19(24-3)17(22)11-14(13)15(20)8-12-4-5-18(23-2)16(21)9-12/h4-5,9-11,15,21-22H,6-8H2,1-3H3/t15-/m0/s1

> <INCHI_KEY>
BHLYRWXGMIUIHG-HNNXBMFYSA-N

> <FORMULA>
C19H23NO4

> <MOLECULAR_WEIGHT>
329.3902

> <EXACT_MASS>
329.162708229

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
47

> <JCHEM_AVERAGE_POLARIZABILITY>
36.14650233241288

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <ALOGPS_LOGP>
2.71

> <JCHEM_LOGP>
3.1049593069999997

> <ALOGPS_LOGS>
-3.28

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
10.36995691314734

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.763064568264014

> <JCHEM_PKA_STRONGEST_BASIC>
7.810592585816691

> <JCHEM_POLAR_SURFACE_AREA>
62.160000000000004

> <JCHEM_REFRACTIVITY>
93.83630000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.72e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(+,-)-reticuline

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 15-JUL-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   15-JUL-20         0                                  
HETATM    1  C   UNK     0    8666.8088666.678   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0    8669.4728665.134   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0    8669.4808671.298   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0    8661.4848665.134   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0    8672.1448669.758   0.000  0.00  0.00           O+0
HETATM    6  O   UNK     0    8661.4848662.043   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0    8673.4808668.988   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0    8659.8908662.960   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0    8670.8108668.988   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0    8669.4768669.758   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0    8668.1428668.988   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0    8668.1428667.448   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0    8669.4768666.678   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0    8670.8108667.448   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0    8664.1488665.126   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0    8662.8148664.356   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0    8662.8148662.817   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0    8664.1478662.046   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0    8666.8098665.127   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0    8665.4758664.357   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0    8665.4758662.816   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0    8666.8098662.047   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0    8668.1428662.816   0.000  0.00  0.00           C+0
HETATM   24  N   UNK     0    8668.1428664.357   0.000  0.00  0.00           N+0
CONECT    1   12   19                                                       
CONECT    2   24                                                            
CONECT    3   10                                                            
CONECT    4   16                                                            
CONECT    5    7    9                                                       
CONECT    6    8   17                                                       
CONECT    7    5                                                            
CONECT    8    6                                                            
CONECT    9   10   14    5                                                  
CONECT   10    9   11    3                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13    1                                                  
CONECT   13   12   14                                                       
CONECT   14   13    9                                                       
CONECT   15   16   20                                                       
CONECT   16   15   17    4                                                  
CONECT   17   16   18    6                                                  
CONECT   18   17   21                                                       
CONECT   19   20   24    1                                                  
CONECT   20   19   21   15                                                  
CONECT   21   20   22   18                                                  
CONECT   22   21   23                                                       
CONECT   23   22   24                                                       
CONECT   24   19   23    2                                                  
MASTER        0    0    0    0    0    0    0    0   24    0   52    0
END

View in JSmol

Synonyms

Value	Source
(+)-Reticuline	ChEBI
(S)-(+)-Reticuline	ChEBI
L-(+)-Reticuline	ChEBI
Reticline	ChEBI
Reticulin	HMDB
Reticuline	HMDB
S-(+)-Reticuline	HMDB
(1S)-1,2,3,4-Tetrahydro-1-[(3-hydroxy-4-methoxyphenyl)methyl]-6-methoxy-2-methyl-7-isoquinolinol	HMDB
(S)-Reticulene	HMDB
(S)-Reticuline	HMDB

Chemical Formula

C₁₉H₂₃NO₄

Average Mass

329.3902 Da

Monoisotopic Mass

329.16271 Da

IUPAC Name

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

Traditional Name

(+,-)-reticuline

CAS Registry Number

Not Available

SMILES

COC1=C(O)C=C(C[C@@H]2N(C)CCC3=CC(OC)=C(O)C=C23)C=C1

InChI Identifier

InChI=1S/C19H23NO4/c1-20-7-6-13-10-19(24-3)17(22)11-14(13)15(20)8-12-4-5-18(23-2)16(21)9-12/h4-5,9-11,15,21-22H,6-8H2,1-3H3/t15-/m0/s1

InChI Key

BHLYRWXGMIUIHG-HNNXBMFYSA-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
Aconitum zeravschanicum	LOTUS Database	35616633
Annona cherimola	LOTUS Database	35616633
Annona emarginata	LOTUS Database	35616633
Annona glabra	LOTUS Database	35616633
Annona purpurea	LOTUS Database	35616633
Annona reticulata	LOTUS Database	35616633
Argemone mexicana	LOTUS Database	35616633
Argemone platyceras	LOTUS Database	35616633
Aristolochia gigantea	LOTUS Database	35616633
Artabotrys hexapetalus	LOTUS Database	35616633
Artabotrys monteiroae	LOTUS Database	35616633
Artabotrys venustus	LOTUS Database	35616633
Berberis heteropoda	LOTUS Database	35616633
Berberis integerrima	LOTUS Database	35616633
Berberis nummularia	LOTUS Database	35616633
Berberis stolonifera	LOTUS Database	35616633
Bongardia chrysogonum	LOTUS Database	35616633
Cissampelos capensis	LOTUS Database	35616633
Clematis parviloba	LOTUS Database	35616633
Coptis japonica	LOTUS Database	35616633
Corydalis taliensis	LOTUS Database	35616633
Croton celtidifolius	LOTUS Database	35616633
Croton hemiargyreus	LOTUS Database	35616633
Cymbopetalum brasiliense	LOTUS Database	35616633
Dehaasia hainanensis	LOTUS Database	35616633
Delphinium pentagynum	LOTUS Database	35616633
Dicentra peregrina	LOTUS Database	35616633
Erythrina variegata	LOTUS Database	35616633
Fumaria capreolata	LOTUS Database	35616633
Fumaria vaillantii	LOTUS Database	35616633
Glaucium corniculatum	LOTUS Database	35616633
Glaucium fimbrilligerum	LOTUS Database	35616633
Glaucium flavum	LOTUS Database	35616633
Glossocalyx brevipes	LOTUS Database	35616633
Greenwayodendron oliveri	LOTUS Database	35616633
Guatteria juruensis	LOTUS Database	35616633
Gyrocarpus americanus	LOTUS Database	35616633
Hernandia nymphaeifolia	LOTUS Database	35616633
Hypserpa nitida	LOTUS Database	35616633
Isopyrum thalictroides	LOTUS Database	35616633
Laureliopsis philippiana	LOTUS Database	35616633
Laurobasidium lauri	LOTUS Database	35616633
Laurus nobilis	LOTUS Database	35616633
Leontice leontopetalum	LOTUS Database	35616633
Leptadenia reticulata	LOTUS Database	35616633
Lindera aggregata	LOTUS Database	35616633
Lindera glauca	LOTUS Database	35616633
Lindera megaphylla	LOTUS Database	35616633
Litsea cubeba	LOTUS Database	35616633
Litsea elliptica	LOTUS Database	35616633
Litsea lancifolia	LOTUS Database	35616633
Magnolia officinalis	LOTUS Database	35616633
Magnolia salicifolia	LOTUS Database	35616633
Miliusa velutina	LOTUS Database	35616633
Monocyclanthus vignei	LOTUS Database	35616633
Neolitsea aciculata	LOTUS Database	35616633
Neolitsea konishii	LOTUS Database	35616633
Ocotea velloziana	LOTUS Database	35616633
Pachygone ovata	LOTUS Database	35616633
Papaver somniferum	LOTUS Database	35616633
Stephania cephalantha	LOTUS Database	35616633
Stephania pierrei	LOTUS Database	35616633
Stephania venosa	LOTUS Database	35616633
Stephania viridiflavens	LOTUS Database	35616633
Thalictrum foliolosum	LOTUS Database	35616633
Uvaria dulcis	LOTUS Database	35616633
Xylopia parviflora	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
Methoxyphenol
Tetrahydroisoquinoline
Phenoxy compound
Anisole
Methoxybenzene
Phenol ether
Alkyl aryl ether
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Aralkylamine
Phenol
Monocyclic benzene moiety
Benzenoid
Tertiary aliphatic amine
Tertiary amine
Ether
Azacycle
Amine
Organic nitrogen compound
Hydrocarbon derivative
Organopnictogen compound
Organic oxygen compound
Organonitrogen compound
Organooxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

reticuline (CHEBI:16718 )
Isoquinoline alkaloids (C02105 )

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	2.71	ALOGPS
logP	3.1	ChemAxon
logS	-3.3	ALOGPS
pKa (Strongest Acidic)	9.76	ChemAxon
pKa (Strongest Basic)	7.81	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	62.16 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	93.84 m³·mol⁻¹	ChemAxon
Polarizability	36.15 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

HMDB0003601

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

6967

PubChem Compound

439653

PDB ID

Not Available

ChEBI ID

16718

Good Scents ID

Not Available

References

General References

Al-Amri AM, Smith RM, El-Haj BM, Juma'a MH: The GC-MS detection and characterization of reticuline as a marker of opium use. Forensic Sci Int. 2004 May 28;142(1):61-9. doi: 10.1016/j.forsciint.2004.02.006. [PubMed:15272474 ]
Al-Amri AM, Smith RM, El-Haj BM, Juma'a MH: The GC-MS detection and characterization of reticuline as a marker of opium use. Forensic Sci Int. 2004 Mar 10;140(2-3):175-83. doi: 10.1016/j.forsciint.2003.10.022. [PubMed:15036439 ]
Poeaknapo C, Schmidt J, Brandsch M, Drager B, Zenk MH: Endogenous formation of morphine in human cells. Proc Natl Acad Sci U S A. 2004 Sep 28;101(39):14091-6. doi: 10.1073/pnas.0405430101. Epub 2004 Sep 21. [PubMed:15383669 ]
Poeaknapo C: Mammalian morphine: de novo formation of morphine in human cells. Med Sci Monit. 2005 May;11(5):MS6-17. Epub 2005 Apr 28. [PubMed:15874902 ]
Boettcher C, Fellermeier M, Boettcher C, Drager B, Zenk MH: How human neuroblastoma cells make morphine. Proc Natl Acad Sci U S A. 2005 Jun 14;102(24):8495-500. doi: 10.1073/pnas.0503244102. Epub 2005 Jun 3. [PubMed:15937106 ]
LOTUS database [Link]

Showing NP-Card for (+,-)-reticuline (NP0266007)

MOL for NP0266007 ((+,-)-reticuline)

3D MOL for NP0266007 ((+,-)-reticuline)

3D SDF for NP0266007 ((+,-)-reticuline)

3D-SDF for NP0266007 ((+,-)-reticuline)

PDB for NP0266007 ((+,-)-reticuline)

3D PDB for NP0266007 ((+,-)-reticuline)

SMILES for NP0266007 ((+,-)-reticuline)

INCHI for NP0266007 ((+,-)-reticuline)

Structure for NP0266007 ((+,-)-reticuline)

3D Structure for NP0266007 ((+,-)-reticuline)