NP-MRD: Showing NP-Card for yuremamine (NP0156347)

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Record Information

Version

2.0

Created at

2022-09-02 13:32:22 UTC

Updated at

2022-09-02 13:32:22 UTC

NP-MRD ID

NP0156347

Secondary Accession Numbers

None

Natural Product Identification

Common Name

yuremamine

Description

Yuremamine belongs to the class of organic compounds known as 3-alkylindoles. 3-Alkylindoles are compounds containing an indole moiety that carries an alkyl chain at the 3-position. yuremamine is found in Mimosa tenuiflora. yuremamine was first documented in 2016 (PMID: 27494137). Based on a literature review a small amount of articles have been published on yuremamine (PMID: 35723216) (PMID: 32896230) (PMID: 28902520) (PMID: 26891188).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309022215322D          

 35 39  0  0  1  0            999 V2000
    0.5755    3.9890    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2817    3.5624    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.0041    3.9608    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2654    2.7376    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9716    2.3111    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9554    1.4863    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6131    0.9883    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3427    0.2088    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.5179    0.2251    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9539   -0.3770    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1505   -0.1896    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0890    0.5999    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4750    1.2020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2785    1.0146    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0005   -0.2892    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.9842   -1.1140    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6904   -1.5405    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6742   -2.3653    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3804   -2.7918    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9517   -2.7637    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9354   -3.5885    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2455   -2.3372    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5230   -2.7355    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2618   -1.5123    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6774    0.1825    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.4568   -0.0878    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4379    0.9720    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.9359    1.6298    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6153    2.3899    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1133    3.0477    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9319    2.9453    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4299    3.6030    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    4.7545    1.5274    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0752    0.7672    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
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  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
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  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
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 12 13  1  0  0  0  0
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  6 14  1  0  0  0  0
  9 14  1  0  0  0  0
  8 15  1  0  0  0  0
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 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 18 20  2  0  0  0  0
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  7 27  1  0  0  0  0
 27 28  1  6  0  0  0
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 33 34  2  0  0  0  0
 28 34  1  0  0  0  0
 34 35  1  0  0  0  0
M  END

     RDKit          3D

 63 67  0  0  0  0  0  0  0  0999 V2000
    4.5207    1.9071    1.1314 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4509    0.7860    0.2297 N   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.5390   -1.0209   -4.5625 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7931   -0.6137   -4.6641 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3411    0.0040   -3.5693 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6260    0.2201   -2.4173 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3185    0.0501   -0.2932 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.1710   -1.0886   -0.5653 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8966   -2.3397   -0.1079 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7077   -3.4360   -0.3571 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3918   -4.6966    0.1286 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8696   -3.2489   -1.1187 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6872   -4.3309   -1.3752 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1727   -1.9966   -1.5945 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3127   -1.8013   -2.3449 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3213   -0.9145   -1.3169 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7005    0.0285    1.1117 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.6455    0.3592    2.0784 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6782    1.1283    0.9119 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.2580    1.3370    1.9830 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5958    0.3612    2.9015 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5036    0.6009    3.9280 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0985    1.8240    4.0637 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0210    2.1015    5.0902 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7681    2.8113    3.1487 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8652    2.5672    2.1308 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5670    3.6093    1.2326 O   0  0  0  0  0  0  0  0  0  0  0  0
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    3.8606    2.7083    0.7764 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5736    2.3069    1.1488 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8502    0.0666    1.6767 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5292   -1.0538    1.2992 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8625   -0.8159    0.1022 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5634    0.0699    0.8103 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2313   -0.5769   -0.6891 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8931    1.5931   -1.8862 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2992    2.3181   -0.3975 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2796   -1.1287   -3.3571 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9628   -1.5123   -5.4446 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3422   -0.7905   -5.5762 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3591    0.3278   -3.6155 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9204    0.9923   -0.3700 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0205   -2.5161    0.4698 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0100   -5.4673   -0.0762 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5307   -4.3455   -1.8939 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9360   -2.5397   -2.5615 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6159    0.0573   -1.7220 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2398   -0.9314    1.3634 H   0  0  0  0  0  0  0  0  0  0  0  0
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 35 63  1  0
M  END


  Mrv1652309022215322D          

 35 39  0  0  1  0            999 V2000
    0.5755    3.9890    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2817    3.5624    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.0041    3.9608    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2654    2.7376    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    2.3427    0.2088    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
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    3.6904   -1.5405    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6742   -2.3653    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3804   -2.7918    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    4.4568   -0.0878    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    3.6153    2.3899    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    4.7545    1.5274    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0752    0.7672    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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 28 34  1  0  0  0  0
 34 35  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0156347

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CN(C)CCC1=C2[C@@H]([C@@H](O)[C@@H](N2C2=CC=CC=C12)C1=CC(O)=C(O)C(O)=C1)C1=CC=C(O)C=C1O

> <INCHI_IDENTIFIER>
InChI=1S/C27H28N2O6/c1-28(2)10-9-17-16-5-3-4-6-19(16)29-24(14-11-21(32)26(34)22(33)12-14)27(35)23(25(17)29)18-8-7-15(30)13-20(18)31/h3-8,11-13,23-24,27,30-35H,9-10H2,1-2H3/t23-,24-,27+/m0/s1

> <INCHI_KEY>
AGTMZGSAEVWERY-NLJOTIRTSA-N

> <FORMULA>
C27H28N2O6

> <MOLECULAR_WEIGHT>
476.529

> <EXACT_MASS>
476.19473663

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
63

> <JCHEM_AVERAGE_POLARIZABILITY>
50.857143711522305

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
6

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
5-[(1S,2R,3S)-1-(2,4-dihydroxyphenyl)-9-[2-(dimethylamino)ethyl]-2-hydroxy-1H,2H,3H-benzo[b]pyrrolizin-3-yl]benzene-1,2,3-triol

> <ALOGPS_LOGP>
3.20

> <JCHEM_LOGP>
2.493871857012953

> <ALOGPS_LOGS>
-3.44

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
9.708528374737195

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.720843326432055

> <JCHEM_PKA_STRONGEST_BASIC>
9.234773748006855

> <JCHEM_POLAR_SURFACE_AREA>
129.55

> <JCHEM_REFRACTIVITY>
133.29760000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.72e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
5-[(1S,2R,3S)-1-(2,4-dihydroxyphenyl)-9-[2-(dimethylamino)ethyl]-2-hydroxy-1H,2H,3H-benzo[b]pyrrolizin-3-yl]benzene-1,2,3-triol

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 02-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   02-SEP-22         0                                  
HETATM    1  C   UNK     0       1.074   7.446   0.000  0.00  0.00           C+0
HETATM    2  N   UNK     0       2.392   6.650   0.000  0.00  0.00           N+0
HETATM    3  C   UNK     0       3.741   7.393   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.362   5.110   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       3.680   4.314   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       3.650   2.774   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.878   1.845   0.000  0.00  0.00           C+0
HETATM    8  N   UNK     0       4.373   0.390   0.000  0.00  0.00           N+0
HETATM    9  C   UNK     0       2.833   0.420   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.781  -0.704   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.281  -0.354   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -0.166   1.120   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       0.887   2.244   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.387   1.894   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       5.601  -0.540   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       5.571  -2.079   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       6.889  -2.876   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       6.858  -4.415   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       8.177  -5.211   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       5.510  -5.159   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       5.479  -6.699   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       4.192  -4.363   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       2.843  -5.106   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0       4.222  -2.823   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       6.864   0.341   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0       8.319  -0.164   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0       6.417   1.814   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       7.347   3.042   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       6.749   4.461   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       7.678   5.689   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       9.206   5.498   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0      10.136   6.726   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0       9.805   4.079   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       8.875   2.851   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0       9.474   1.432   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7   14                                                  
CONECT    7    6    8   27                                                  
CONECT    8    7    9   15                                                  
CONECT    9    8   10   14                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13    6    9                                                  
CONECT   15    8   16   25                                                  
CONECT   16   15   17   24                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22   16                                                       
CONECT   25   15   26   27                                                  
CONECT   26   25                                                            
CONECT   27   25    7   28                                                  
CONECT   28   27   29   34                                                  
CONECT   29   28   30                                                       
CONECT   30   29   31                                                       
CONECT   31   30   32   33                                                  
CONECT   32   31                                                            
CONECT   33   31   34                                                       
CONECT   34   33   28   35                                                  
CONECT   35   34                                                            
MASTER        0    0    0    0    0    0    0    0   35    0   78    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₇H₂₈N₂O₆

Average Mass

476.5290 Da

Monoisotopic Mass

476.19474 Da

IUPAC Name

5-[(1S,2R,3S)-1-(2,4-dihydroxyphenyl)-9-[2-(dimethylamino)ethyl]-2-hydroxy-1H,2H,3H-benzo[b]pyrrolizin-3-yl]benzene-1,2,3-triol

Traditional Name

5-[(1S,2R,3S)-1-(2,4-dihydroxyphenyl)-9-[2-(dimethylamino)ethyl]-2-hydroxy-1H,2H,3H-benzo[b]pyrrolizin-3-yl]benzene-1,2,3-triol

CAS Registry Number

Not Available

SMILES

CN(C)CCC1=C2[C@@H]([C@@H](O)[C@@H](N2C2=CC=CC=C12)C1=CC(O)=C(O)C(O)=C1)C1=CC=C(O)C=C1O

InChI Identifier

InChI=1S/C27H28N2O6/c1-28(2)10-9-17-16-5-3-4-6-19(16)29-24(14-11-21(32)26(34)22(33)12-14)27(35)23(25(17)29)18-8-7-15(30)13-20(18)31/h3-8,11-13,23-24,27,30-35H,9-10H2,1-2H3/t23-,24-,27+/m0/s1

InChI Key

AGTMZGSAEVWERY-NLJOTIRTSA-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
Mimosa tenuiflora	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 3-alkylindoles. 3-Alkylindoles are compounds containing an indole moiety that carries an alkyl chain at the 3-position.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Indoles and derivatives

Sub Class

Indoles

Direct Parent

3-alkylindoles

Alternative Parents

Substituents

3-alkylindole
Benzenetriol
Pyrogallol derivative
Pyrrolizine
Resorcinol
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Phenol
Aralkylamine
Monocyclic benzene moiety
Benzenoid
Substituted pyrrole
Heteroaromatic compound
Pyrrole
Tertiary aliphatic amine
Tertiary amine
Secondary alcohol
Azacycle
Polyol
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
Organic oxygen compound
Organic nitrogen compound
Alcohol
Amine
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
logP	3.2	ALOGPS
logP	2.49	ChemAxon
logS	-3.4	ALOGPS
pKa (Strongest Acidic)	8.72	ChemAxon
pKa (Strongest Basic)	9.23	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	129.55 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	133.3 m³·mol⁻¹	ChemAxon
Polarizability	50.86 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	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

27444969

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Yuremamine

METLIN ID

Not Available

PubChem Compound

102516368

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Duarte-Filho LAMS, Amariz IA, Nishimura RHV, Massaranduba ABR, Menezes PMN, Damasceno TA, Brys I, Rolim LA, Silva FS, Ribeiro LAA: beta-carboline-independent antidepressant-like effect of the standardized extract of the barks of Mimosa tenuiflora (Willd) Poir. occurs via 5-HT(2A/2C) receptors in mice. J Psychopharmacol. 2022 Jul;36(7):836-848. doi: 10.1177/02698811221104050. Epub 2022 Jun 20. [PubMed:35723216 ]
Kaasik H, Souza RCZ, Zandonadi FS, Tofoli LF, Sussulini A: Chemical Composition of Traditional and Analog Ayahuasca. J Psychoactive Drugs. 2021 Jan-Mar;53(1):65-75. doi: 10.1080/02791072.2020.1815911. Epub 2020 Sep 8. [PubMed:32896230 ]
Gharpure SJ, Shelke YG: Cascade Radical Cyclization of N-Propargylindoles: Substituents Dictate Stereoselective Formation of N-Fused Indolines versus Indoles. Org Lett. 2017 Oct 6;19(19):5022-5025. doi: 10.1021/acs.orglett.7b02005. Epub 2017 Sep 13. [PubMed:28902520 ]
Ghosh A, Bainbridge DT, Stanley LM: Enantioselective Model Synthesis and Progress toward the Putative Structure of Yuremamine. J Org Chem. 2016 Sep 2;81(17):7945-51. doi: 10.1021/acs.joc.6b01730. Epub 2016 Aug 24. [PubMed:27494137 ]
Calvert MB, Sperry J: Synthetic studies towards putative yuremamine using an iterative C(sp(3))-H arylation strategy. Org Biomol Chem. 2016 Jun 28;14(24):5728-43. doi: 10.1039/c6ob00110f. Epub 2016 Feb 18. [PubMed:26891188 ]
LOTUS database [Link]

Showing NP-Card for yuremamine (NP0156347)

MOL for NP0156347 (yuremamine)

3D MOL for NP0156347 (yuremamine)

3D SDF for NP0156347 (yuremamine)

3D-SDF for NP0156347 (yuremamine)

PDB for NP0156347 (yuremamine)

3D PDB for NP0156347 (yuremamine)

SMILES for NP0156347 (yuremamine)

INCHI for NP0156347 (yuremamine)

Structure for NP0156347 (yuremamine)

3D Structure for NP0156347 (yuremamine)