NP-MRD: Showing NP-Card for Broussinol (NP0056144)

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Record Information

Version

2.0

Created at

2022-04-28 02:00:33 UTC

Updated at

2022-04-28 02:00:33 UTC

NP-MRD ID

NP0056144

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Broussinol

Description

Broussinol belongs to the class of organic compounds known as 3'-prenylated flavans. These are flavans that features a C5-isoprenoid substituent at the 3'-position. Thus, broussinol is considered to be a flavonoid. Broussinol is found in Broussonetia papyrifera . Based on a literature review very few articles have been published on Broussinol.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 46 48  0  0  0  0  0  0  0  0999 V2000
    4.5710   -0.8517   -1.3908 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7677   -0.5672    0.0476 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5278   -1.4990    0.9301 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2637    0.5321    0.5732 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5043    1.4680   -0.2943 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1275    1.5658    0.3020 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0995    0.8461   -0.2882 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1927    0.8573    0.1921 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3044    0.0943   -0.4261 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.0251   -0.5425    0.5976 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2894   -1.0481    0.2682 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9151   -1.8387    1.2338 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1559   -2.3661    0.9764 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8058   -3.1656    1.9345 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7481   -2.0946   -0.2392 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1301   -1.3137   -1.1933 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8888   -0.7817   -0.9447 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1835    0.0762   -1.9626 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2626    0.9843   -1.1720 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.6236    1.9234   -1.9593 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4398    1.6292    1.3111 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5796    2.3452    1.8989 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8832    2.3390    1.4209 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8870    3.0710    2.0318 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0596   -1.8141   -1.6756 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4672   -0.9431   -1.5900 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9575   -0.0137   -1.9891 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8309   -2.3451    1.1494 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4314   -1.8860    0.4055 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8144   -0.9679    1.8482 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4022    0.7563    1.6509 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9576    2.4854   -0.2996 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3938    1.0458   -1.2924 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2837    0.2292   -1.1774 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9302   -0.6746   -1.1316 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4212   -2.0256    2.1659 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3370   -3.3389    2.8105 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7361   -2.5171   -0.4367 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5881   -1.0953   -2.1518 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5871   -0.6105   -2.5977 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9149    0.6473   -2.5685 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9056    1.5000   -0.4025 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1578    2.2601   -2.6955 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4598    1.6376    1.6904 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3748    2.9550    2.7861 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8180    3.0523    1.6537 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  2  3
  4  5  1  0
  5  6  1  0
  6 23  2  0
 23 24  1  0
 23 22  1  0
 22 21  2  0
 21  8  1  0
  8  7  2  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  1  0
 13 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
  7  6  1  0
 19  9  1  0
 17 11  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
  3 28  1  0
  3 29  1  0
  3 30  1  0
  4 31  1  0
  5 32  1  0
  5 33  1  0
 24 46  1  0
 22 45  1  0
 21 44  1  0
  7 34  1  0
  9 35  1  6
 12 36  1  0
 14 37  1  0
 15 38  1  0
 16 39  1  0
 18 40  1  0
 18 41  1  0
 19 42  1  1
 20 43  1  0
M  END


  Mrv1652304282204002D          

 24 26  0  0  1  0            999 V2000
   -0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  1  6  1  0  0  0  0
  5  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  4 10  1  0  0  0  0
  9 11  1  1  0  0  0
  8 12  1  6  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 12 17  1  0  0  0  0
 15 18  1  0  0  0  0
 14 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 21 22  1  0  0  0  0
 21 23  1  0  0  0  0
  1 24  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0056144

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)=CCC1=C(O)C=CC(=C1)[C@H]1OC2=CC(O)=CC=C2C[C@@H]1O

> <INCHI_IDENTIFIER>
InChI=1S/C20H22O4/c1-12(2)3-4-13-9-15(6-8-17(13)22)20-18(23)10-14-5-7-16(21)11-19(14)24-20/h3,5-9,11,18,20-23H,4,10H2,1-2H3/t18-,20+/m0/s1

> <INCHI_KEY>
PTZNBCJWCJFLPQ-AZUAARDMSA-N

> <FORMULA>
C20H22O4

> <MOLECULAR_WEIGHT>
326.392

> <EXACT_MASS>
326.151809188

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
46

> <JCHEM_AVERAGE_POLARIZABILITY>
34.78059891999695

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2R,3S)-2-[4-hydroxy-3-(3-methylbut-2-en-1-yl)phenyl]-3,4-dihydro-2H-1-benzopyran-3,7-diol

> <ALOGPS_LOGP>
3.20

> <JCHEM_LOGP>
4.130804658

> <ALOGPS_LOGS>
-4.21

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.845114072188652

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.133738989727187

> <JCHEM_PKA_STRONGEST_BASIC>
-3.263384374061692

> <JCHEM_POLAR_SURFACE_AREA>
69.92

> <JCHEM_REFRACTIVITY>
94.28070000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.03e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
broussinol

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 28-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   28-APR-22         0                                  
HETATM    1  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.000  -3.080   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.000  -0.000   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       2.667  -0.000   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       5.335  -3.080   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       5.335  -0.000   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       5.335   1.540   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       6.668   2.310   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       8.002   1.540   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       8.002  -0.000   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       9.336   2.310   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       6.668   3.850   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       5.335   4.620   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       5.335   6.160   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       4.001   6.930   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       6.668   6.930   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0      -2.667   0.000   0.000  0.00  0.00           O+0
CONECT    1    2    6   24                                                  
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5   10                                                  
CONECT    5    4    6    7                                                  
CONECT    6    5    1                                                       
CONECT    7    5    8                                                       
CONECT    8    7    9   12                                                  
CONECT    9    8   10   11                                                  
CONECT   10    9    4                                                       
CONECT   11    9                                                            
CONECT   12    8   13   17                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15   19                                                  
CONECT   15   14   16   18                                                  
CONECT   16   15   17                                                       
CONECT   17   16   12                                                       
CONECT   18   15                                                            
CONECT   19   14   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21                                                            
CONECT   24    1                                                            
MASTER        0    0    0    0    0    0    0    0   24    0   52    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₀H₂₂O₄

Average Mass

326.3920 Da

Monoisotopic Mass

326.15181 Da

IUPAC Name

(2R,3S)-2-[4-hydroxy-3-(3-methylbut-2-en-1-yl)phenyl]-3,4-dihydro-2H-1-benzopyran-3,7-diol

Traditional Name

broussinol

CAS Registry Number

Not Available

SMILES

CC(C)=CCC1=C(O)C=CC(=C1)[C@H]1OC2=CC(O)=CC=C2C[C@@H]1O

InChI Identifier

InChI=1S/C20H22O4/c1-12(2)3-4-13-9-15(6-8-17(13)22)20-18(23)10-14-5-7-16(21)11-19(14)24-20/h3,5-9,11,18,20-23H,4,10H2,1-2H3/t18-,20+/m0/s1

InChI Key

PTZNBCJWCJFLPQ-AZUAARDMSA-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, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, 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
Broussonetia papyrifera	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 3'-prenylated flavans. These are flavans that features a C5-isoprenoid substituent at the 3'-position.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Flavonoids

Sub Class

Flavans

Direct Parent

3'-prenylated flavans

Alternative Parents

Substituents

3'-prenylated flavan
3-hydroxyflavonoid
4'-hydroxyflavonoid
7-hydroxyflavonoid
Flavan-3-ol
Hydroxyflavonoid
1-benzopyran
Chromane
Benzopyran
1-hydroxy-2-unsubstituted benzenoid
Phenol
Alkyl aryl ether
Benzenoid
Monocyclic benzene moiety
Secondary alcohol
Organoheterocyclic compound
Oxacycle
Ether
Organooxygen compound
Hydrocarbon derivative
Organic oxygen compound
Alcohol
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Flavans, Flavanols and Leucoanthocyanidins (LMPK12020005 )

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	4.13	ChemAxon
logS	-4.2	ALOGPS
pKa (Strongest Acidic)	9.13	ChemAxon
pKa (Strongest Basic)	-3.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	69.92 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	94.28 m³·mol⁻¹	ChemAxon
Polarizability	34.78 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

Not Available

KNApSAcK ID

C00008911

Chemspider ID

24842492

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

44257049

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Broussinol (NP0056144)

MOL for NP0056144 (Broussinol)

3D MOL for NP0056144 (Broussinol)

3D SDF for NP0056144 (Broussinol)

3D-SDF for NP0056144 (Broussinol)

PDB for NP0056144 (Broussinol)

3D PDB for NP0056144 (Broussinol)

SMILES for NP0056144 (Broussinol)

INCHI for NP0056144 (Broussinol)

Structure for NP0056144 (Broussinol)

3D Structure for NP0056144 (Broussinol)