Np mrd loader

Showing NP-Card for Guavin B (NP0047593)

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Record Information
Version2.0
Created at2022-03-17 20:42:44 UTC
Updated at2022-03-17 20:42:44 UTC
NP-MRD IDNP0047593
Secondary Accession NumbersNone
Natural Product Identification
Common NameGuavin B
Description5-(4-Chloro-3-hydroxy-1-butynyl)-2,2'-bithiophene, also known as 1-chloro-4-[5-(3-thienyl)-2-thienyl]-3-butyn-2-ol, 8CI, belongs to the class of organic compounds known as bi- and oligothiophenes. These are organic compounds containing two or more linked thiophene rings. Thiophene is a five-member aromatic ring with one sulfur and four carbon atoms. 5-(4-Chloro-3-hydroxy-1-butynyl)-2,2'-bithiophene is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, 5-(4-Chloro-3-hydroxy-1-butynyl)-2,2'-bithiophene has been detected, but not quantified in, herbs and spices. This could make 5-(4-chloro-3-hydroxy-1-butynyl)-2,2'-bithiophene a potential biomarker for the consumption of these foods.
Structure
Thumb
MOLSDFPDBSMILESInChI

MOL for NP0047593 (Guavin B)


  Mrv0541 05061307012D          

 50 55  0  0  0  0            999 V2000
    1.9948    3.6909    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3463    4.2009    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8774    2.8743    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5804    3.8943    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1115    2.5677    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3036    0.8312    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1108    0.6279    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6025   -0.6987    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0740   -4.0458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8306   -0.5852    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4630    3.0777    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6551    0.3213    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9540   -1.2087    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0347   -3.2218    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1862    1.6479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2282    1.4445    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3684   -1.0053    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8072   -4.4239    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2904   -1.2087    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0714   -2.0253    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7287   -2.7757    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4203    1.9545    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3029    2.7711    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4858   -1.8219    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5013   -3.9778    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8374   -2.3319    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4620   -3.1538    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.2415   -1.8219    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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 49 19  1  0  0  0  0
 49 33  1  0  0  0  0
 50 30  1  0  0  0  0
 50 32  1  0  0  0  0
M  END
Download

3D MOL for NP0047593 (Guavin B)

Download
3D SDF for NP0047593 (Guavin B)

  Mrv0541 05061307012D          

 50 55  0  0  0  0            999 V2000
    1.9948    3.6909    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3463    4.2009    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8774    2.8743    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5804    3.8943    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1115    2.5677    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3036    0.8312    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1108    0.6279    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6025   -0.6987    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0740   -4.0458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8306   -0.5852    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4630    3.0777    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6551    0.3213    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    3.0347   -3.2218    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    0.2282    1.4445    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3684   -1.0053    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8072   -4.4239    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    4.0714   -2.0253    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7287   -2.7757    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4203    1.9545    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3029    2.7711    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4858   -1.8219    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5013   -3.9778    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8374   -2.3319    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4620   -3.1538    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4070   -2.3319    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2415   -1.8219    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1729   -2.0253    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4138   -0.5852    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2097   -3.2218    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1240   -1.0053    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8347    2.1578    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    6.2517   -2.1285    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    2.6222   -0.3528    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    0.6419   -0.6987    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5157   -2.7757    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0  0  0  0
  3  1  1  0  0  0  0
  4  2  1  0  0  0  0
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 11  4  2  0  0  0  0
 11  5  1  0  0  0  0
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 12  7  1  0  0  0  0
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 37 18  1  0  0  0  0
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 47 10  1  0  0  0  0
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 48 12  1  0  0  0  0
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 50 30  1  0  0  0  0
 50 32  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0047593

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC1C(O)C2OC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OCC2OC1OC1=CC(O)=C(C(=O)C2=CC=CC=C2)C(O)=C1

> <INCHI_IDENTIFIER>
InChI=1S/C33H26O17/c34-15-6-12(7-16(35)22(15)23(38)11-4-2-1-3-5-11)48-33-29(44)28(43)30-19(49-33)10-47-31(45)13-8-17(36)24(39)26(41)20(13)21-14(32(46)50-30)9-18(37)25(40)27(21)42/h1-9,19,28-30,33-37,39-44H,10H2

> <INCHI_KEY>
RPZNIDVYYGUDPA-UHFFFAOYSA-N

> <FORMULA>
C33H26O17

> <MOLECULAR_WEIGHT>
694.5493

> <EXACT_MASS>
694.116999406

> <JCHEM_ACCEPTOR_COUNT>
15

> <JCHEM_AVERAGE_POLARIZABILITY>
64.00276209058036

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
10

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
13-(4-benzoyl-3,5-dihydroxyphenoxy)-3,4,5,11,12,21,22,23-octahydroxy-9,14,17-trioxatetracyclo[17.4.0.0²,⁷.0¹⁰,¹⁵]tricosa-1(23),2,4,6,19,21-hexaene-8,18-dione

> <ALOGPS_LOGP>
2.84

> <JCHEM_LOGP>
3.9970221083333333

> <ALOGPS_LOGS>
-2.91

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
7.8377313571954685

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.350677386556218

> <JCHEM_PKA_STRONGEST_BASIC>
-5.67596783921502

> <JCHEM_POLAR_SURFACE_AREA>
290.43

> <JCHEM_REFRACTIVITY>
165.32820000000012

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
8.55e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
13-(4-benzoyl-3,5-dihydroxyphenoxy)-3,4,5,11,12,21,22,23-octahydroxy-9,14,17-trioxatetracyclo[17.4.0.0²,⁷.0¹⁰,¹⁵]tricosa-1(23),2,4,6,19,21-hexaene-8,18-dione

> <JCHEM_VEBER_RULE>
0

$$$$

Download
3D-SDF for NP0047593 (Guavin B)
Download
PDB for NP0047593 (Guavin B)
HEADER    PROTEIN                                 06-MAY-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAY-13         0                                  
HETATM    1  C   UNK     0       3.724   6.890   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.513   7.842   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       3.504   5.365   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.083   7.269   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.075   4.793   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -2.433   1.552   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.207   1.172   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       8.591  -1.304   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.738  -7.552   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       3.417  -1.092   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.864   5.745   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -1.223   0.600   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       7.381  -2.256   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       5.665  -6.014   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -2.214   3.076   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       0.426   2.696   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      10.021  -1.877   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       7.107  -8.258   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       2.409  -2.256   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       7.600  -3.781   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       6.960  -5.181   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -0.785   3.648   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -0.565   5.173   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      10.240  -3.401   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       8.402  -7.425   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       9.030  -4.353   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       8.329  -5.887   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       0.760  -4.353   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      -0.451  -3.401   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       2.189  -3.781   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       6.372  -1.092   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       4.125  -6.014   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      -0.231  -1.877   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0      -3.425   4.028   0.000  0.00  0.00           O+0
HETATM   35  O   UNK     0       1.856   3.269   0.000  0.00  0.00           O+0
HETATM   36  O   UNK     0      11.232  -0.925   0.000  0.00  0.00           O+0
HETATM   37  O   UNK     0       7.180  -9.796   0.000  0.00  0.00           O+0
HETATM   38  O   UNK     0      -1.776   6.125   0.000  0.00  0.00           O+0
HETATM   39  O   UNK     0      11.670  -3.973   0.000  0.00  0.00           O+0
HETATM   40  O   UNK     0       9.771  -8.131   0.000  0.00  0.00           O+0
HETATM   41  O   UNK     0       9.249  -5.877   0.000  0.00  0.00           O+0
HETATM   42  O   UNK     0       9.764  -6.446   0.000  0.00  0.00           O+0
HETATM   43  O   UNK     0       0.541  -5.877   0.000  0.00  0.00           O+0
HETATM   44  O   UNK     0      -1.880  -3.973   0.000  0.00  0.00           O+0
HETATM   45  O   UNK     0       7.205   0.203   0.000  0.00  0.00           O+0
HETATM   46  O   UNK     0       3.691  -7.491   0.000  0.00  0.00           O+0
HETATM   47  O   UNK     0       4.895  -0.659   0.000  0.00  0.00           O+0
HETATM   48  O   UNK     0      -1.442  -0.925   0.000  0.00  0.00           O+0
HETATM   49  O   UNK     0       1.198  -1.304   0.000  0.00  0.00           O+0
HETATM   50  O   UNK     0       2.829  -5.181   0.000  0.00  0.00           O+0
CONECT    1    2    3                                                       
CONECT    2    1    4                                                       
CONECT    3    1    5                                                       
CONECT    4    2   11                                                       
CONECT    5    3   11                                                       
CONECT    6   12   15                                                       
CONECT    7   12   16                                                       
CONECT    8   13   17                                                       
CONECT    9   14   18                                                       
CONECT   10   19   47                                                       
CONECT   11    4    5   23                                                  
CONECT   12    6    7   48                                                  
CONECT   13    8   20   31                                                  
CONECT   14    9   21   32                                                  
CONECT   15    6   22   34                                                  
CONECT   16    7   22   35                                                  
CONECT   17    8   24   36                                                  
CONECT   18    9   25   37                                                  
CONECT   19   10   30   49                                                  
CONECT   20   13   21   26                                                  
CONECT   21   14   20   27                                                  
CONECT   22   15   16   23                                                  
CONECT   23   11   22   38                                                  
CONECT   24   17   26   39                                                  
CONECT   25   18   27   40                                                  
CONECT   26   20   24   41                                                  
CONECT   27   21   25   42                                                  
CONECT   28   29   30   43                                                  
CONECT   29   28   33   44                                                  
CONECT   30   19   28   50                                                  
CONECT   31   13   45   47                                                  
CONECT   32   14   46   50                                                  
CONECT   33   29   48   49                                                  
CONECT   34   15                                                            
CONECT   35   16                                                            
CONECT   36   17                                                            
CONECT   37   18                                                            
CONECT   38   23                                                            
CONECT   39   24                                                            
CONECT   40   25                                                            
CONECT   41   26                                                            
CONECT   42   27                                                            
CONECT   43   28                                                            
CONECT   44   29                                                            
CONECT   45   31                                                            
CONECT   46   32                                                            
CONECT   47   10   31                                                       
CONECT   48   12   33                                                       
CONECT   49   19   33                                                       
CONECT   50   30   32                                                       
MASTER        0    0    0    0    0    0    0    0   50    0  110    0
END

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3D PDB for NP0047593 (Guavin B)
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SMILES for NP0047593 (Guavin B)
OC1C(O)C2OC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OCC2OC1OC1=CC(O)=C(C(=O)C2=CC=CC=C2)C(O)=C1
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INCHI for NP0047593 (Guavin B)
InChI=1S/C33H26O17/c34-15-6-12(7-16(35)22(15)23(38)11-4-2-1-3-5-11)48-33-29(44)28(43)30-19(49-33)10-47-31(45)13-8-17(36)24(39)26(41)20(13)21-14(32(46)50-30)9-18(37)25(40)27(21)42/h1-9,19,28-30,33-37,39-44H,10H2
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View in JSmol
Synonyms
ValueSource
1-Chloro-4-[5-(3-thienyl)-2-thienyl]-3-butyn-2-ol, 8ciHMDB
Guavin bMeSH
Chemical FormulaC33H26O17
Average Mass694.5493 Da
Monoisotopic Mass694.11700 Da
IUPAC Name13-(4-benzoyl-3,5-dihydroxyphenoxy)-3,4,5,11,12,21,22,23-octahydroxy-9,14,17-trioxatetracyclo[17.4.0.0²,⁷.0¹⁰,¹⁵]tricosa-1(23),2,4,6,19,21-hexaene-8,18-dione
Traditional Name13-(4-benzoyl-3,5-dihydroxyphenoxy)-3,4,5,11,12,21,22,23-octahydroxy-9,14,17-trioxatetracyclo[17.4.0.0²,⁷.0¹⁰,¹⁵]tricosa-1(23),2,4,6,19,21-hexaene-8,18-dione
CAS Registry Number94530-90-2
SMILES
OC1C(O)C2OC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OCC2OC1OC1=CC(O)=C(C(=O)C2=CC=CC=C2)C(O)=C1
InChI Identifier
InChI=1S/C33H26O17/c34-15-6-12(7-16(35)22(15)23(38)11-4-2-1-3-5-11)48-33-29(44)28(43)30-19(49-33)10-47-31(45)13-8-17(36)24(39)26(41)20(13)21-14(32(46)50-30)9-18(37)25(40)27(21)42/h1-9,19,28-30,33-37,39-44H,10H2
InChI KeyRPZNIDVYYGUDPA-UHFFFAOYSA-N
Experimental Spectra
Not Available
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Psidium guajavaFooDB
Chemical Taxonomy
Description Belongs to the class of organic compounds known as bi- and oligothiophenes. These are organic compounds containing two or more linked thiophene rings. Thiophene is a five-member aromatic ring with one sulfur and four carbon atoms.
KingdomOrganic compounds  
Super ClassOrganoheterocyclic compounds  
ClassBi- and oligothiophenes  
Sub ClassNot Available
Direct ParentBi- and oligothiophenes  
Alternative Parents
Substituents
  • Bithiophene
    • 

  • 2,5-disubstituted thiophene
    • 

  • Heteroaromatic compound
    • 

  • Thiophene
    • 

  • Secondary alcohol
    • 

  • Halohydrin
    • 

  • Chlorohydrin
    • 

  • Alcohol
    • 

  • Organooxygen compound
    • 

  • Organochloride
    • 

  • Organohalogen compound
    • 

  • Organic oxygen compound
    • 

  • Alkyl halide
    • 

  • Alkyl chloride
    • 

  • Hydrocarbon derivative
    • 

  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External DescriptorsNot Available
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP2.84ALOGPS
logP4ChemAxon
logS-2.9ALOGPS
pKa (Strongest Acidic)7.35ChemAxon
pKa (Strongest Basic)-5.7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count15ChemAxon
Hydrogen Donor Count10ChemAxon
Polar Surface Area290.43 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity165.33 m³·mol⁻¹ChemAxon
Polarizability64 ųChemAxon
Number of Rings6ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0033269  
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB011292  
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound85528914  
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General ReferencesNot Available