NP-MRD: Showing NP-Card for cyphostemmin b (NP0170700)

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Record Information

Version

2.0

Created at

2022-09-03 06:56:04 UTC

Updated at

2022-09-03 06:56:04 UTC

NP-MRD ID

NP0170700

Secondary Accession Numbers

None

Natural Product Identification

Common Name

cyphostemmin b

Description

Quadrangularin A belongs to the class of organic compounds known as stilbenes. These are organic compounds containing a 1,2-diphenylethylene moiety. Stilbenes (C6-C2-C6 ) are derived from the common phenylpropene (C6-C3) skeleton building block. The introduction of one or more hydroxyl groups to a phenyl ring lead to stilbenoids. Quadrangularin A is a secondary metabolite. Secondary metabolites are metabolically or physiologically non-essential metabolites that may serve a role as defense or signalling molecules. In some cases they are simply molecules that arise from the incomplete metabolism of other secondary metabolites. cyphostemmin b is found in Ampelopsis glandulosa and Cissus quadrangularis. cyphostemmin b was first documented in 2015 (PMID: 25650836). Based on a literature review a small amount of articles have been published on quadrangularin A (PMID: 33836464) (PMID: 28928759) (PMID: 28324165) (PMID: 27490335).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309032208562D          

 34 38  0  0  1  0            999 V2000
   -2.3441    1.4402    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5371    1.2687    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9851    1.8818    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1781    1.7103    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0768    0.9256    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8838    0.7541    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387   -0.0305    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233   -0.2854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378    0.1271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523   -0.2854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0668    0.1271    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523   -1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378   -1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378   -2.3479    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233   -1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387   -1.3654    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.8838   -2.1500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4358   -2.7631    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1809   -3.5477    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3739   -3.7192    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1190   -4.5039    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1781   -3.1062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0768   -2.3215    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6538   -0.6979    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.1712   -0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5837   -1.4124    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4087   -1.4124    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8212   -2.1269    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8212   -0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4087    0.0165    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8212    0.7310    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5837    0.0165    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4752    0.3126    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2822    0.4841    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
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  9 10  1  0  0  0  0
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 15 16  1  0  0  0  0
 16 17  1  1  0  0  0
 17 18  2  0  0  0  0
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 22 23  2  0  0  0  0
 17 23  1  0  0  0  0
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  5 33  1  0  0  0  0
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  2 34  1  0  0  0  0
M  END

     RDKit          3D

 56 60  0  0  0  0  0  0  0  0999 V2000
    4.2012    4.4147   -2.1181 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6429    3.5193   -1.2184 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3442    3.6547   -0.7346 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7734    2.7864    0.1501 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4858    1.7131    0.6087 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9881    0.7300    1.5359 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8785    0.0515    1.4940 C   0  0  0  0  0  0  0  0  0  0  0  0
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    0.1901   -1.9213    4.6791 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5477   -2.0123    6.0370 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7336   -2.7538    4.1204 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1281   -2.7117    2.7810 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0685   -3.5927    2.3060 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5346   -1.7501    1.9583 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6351   -1.3956    0.5444 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.9089   -1.5949   -0.1188 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0312   -0.8671    0.1926 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2240   -1.0612   -0.4730 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3129   -2.0127   -1.4878 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4823   -2.2417   -2.1806 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1919   -2.7411   -1.8002 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0150   -2.5313   -1.1245 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1849    0.0676    0.5118 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0829    0.5011   -0.8403 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7525    1.4060   -1.4498 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5716    1.8422   -2.7400 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4429    2.7585   -3.3137 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5059    1.3491   -3.4705 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3586    0.4395   -2.8796 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4244   -0.0437   -3.6125 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1499    0.0114   -1.5603 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7882    1.5466    0.1460 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3448    2.4282   -0.7421 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7145    5.2409   -1.8733 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7953    4.5268   -1.1214 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7662    2.9642    0.4781 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6445    0.5265    2.4042 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5165   -0.2901    4.2715 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0432   -1.4774    6.7431 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2233   -3.5218    4.7309 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4519   -3.6984    1.4157 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1782   -1.9327   -0.0104 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9701   -0.1143    0.9926 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1270   -0.4815   -0.2289 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1610   -2.9237   -1.8731 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2401   -3.4995   -2.6002 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1376   -3.1339   -1.4023 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0673    0.6131    0.9634 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5859    1.7902   -0.8912 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2178    3.1044   -2.7690 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6357    1.7059   -4.4950 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6111    0.2367   -4.5633 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8514   -0.6920   -1.1760 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3934    0.6906    0.4955 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3780    2.2673   -1.0886 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7 24  1  0
 24 16  1  0
 16 15  1  0
 15 13  2  0
 13 14  1  0
 13 12  1  0
 12 10  2  0
 10 11  1  0
 10  9  1  0
  9  8  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
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 22 23  2  0
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 27 28  1  0
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 29 30  1  0
 30 31  1  0
 30 32  2  0
  5 33  1  0
 33 34  2  0
 34  2  1  0
  8  7  1  0
 23 17  1  0
 32 25  1  0
  8 15  1  0
  1 35  1  0
  3 36  1  0
  4 37  1  0
  6 38  1  0
 24 49  1  1
 16 43  1  6
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  9 39  1  0
 18 44  1  0
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 23 48  1  0
 26 50  1  0
 28 51  1  0
 29 52  1  0
 31 53  1  0
 32 54  1  0
 33 55  1  0
 34 56  1  0
M  END


  Mrv1652309032208562D          

 34 38  0  0  1  0            999 V2000
   -2.3441    1.4402    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5371    1.2687    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9851    1.8818    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1781    1.7103    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0768    0.9256    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8838    0.7541    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387   -0.0305    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233   -0.2854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378    0.1271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523   -0.2854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0668    0.1271    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523   -1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378   -1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378   -2.3479    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    0.8838   -2.1500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4358   -2.7631    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.2822    0.4841    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
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 17 23  1  0  0  0  0
 16 24  1  0  0  0  0
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 26 27  1  0  0  0  0
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M  END
> <DATABASE_ID>
NP0170700

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC1=CC=C(\C=C2/[C@H]([C@@H](C3=C(O)C=C(O)C=C23)C2=CC=C(O)C=C2)C2=CC(O)=CC(O)=C2)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C28H22O6/c29-18-5-1-15(2-6-18)9-23-24-13-22(33)14-25(34)28(24)27(16-3-7-19(30)8-4-16)26(23)17-10-20(31)12-21(32)11-17/h1-14,26-27,29-34H/b23-9-/t26-,27+/m1/s1

> <INCHI_KEY>
BIQMSWPBPAKGSE-PBSLAQMISA-N

> <FORMULA>
C28H22O6

> <MOLECULAR_WEIGHT>
454.478

> <EXACT_MASS>
454.141638428

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
56

> <JCHEM_AVERAGE_POLARIZABILITY>
47.498965839123805

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
6

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1E,2R,3R)-2-(3,5-dihydroxyphenyl)-3-(4-hydroxyphenyl)-1-[(4-hydroxyphenyl)methylidene]-2,3-dihydro-1H-indene-4,6-diol

> <ALOGPS_LOGP>
4.08

> <JCHEM_LOGP>
5.682431151

> <ALOGPS_LOGS>
-5.13

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
8.77650109548562

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.306599216474755

> <JCHEM_PKA_STRONGEST_BASIC>
-5.465631143541423

> <JCHEM_POLAR_SURFACE_AREA>
121.38000000000001

> <JCHEM_REFRACTIVITY>
130.2064

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
3.36e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1E,2R,3R)-2-(3,5-dihydroxyphenyl)-3-(4-hydroxyphenyl)-1-[(4-hydroxyphenyl)methylidene]-2,3-dihydroindene-4,6-diol

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 03-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   03-SEP-22         0                                  
HETATM    1  O   UNK     0      -4.376   2.688   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0      -2.869   2.368   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -1.839   3.513   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -0.333   3.192   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.143   1.728   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.650   1.408   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.126  -0.057   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       3.590  -0.533   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.924   0.237   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       6.258  -0.533   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       7.591   0.237   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       6.258  -2.073   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.924  -2.843   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       4.924  -4.383   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       3.590  -2.073   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       2.126  -2.549   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       1.650  -4.013   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       2.680  -5.158   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       2.204  -6.622   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       0.698  -6.943   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       0.222  -8.407   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0      -0.333  -5.798   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       0.143  -4.334   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       1.220  -1.303   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      -0.320  -1.303   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      -1.090  -2.637   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      -2.630  -2.637   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0      -3.400  -3.970   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0      -3.400  -1.303   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      -2.630   0.031   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0      -3.400   1.365   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0      -1.090   0.031   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      -0.887   0.583   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      -2.393   0.904   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   34                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6   33                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8   24                                                  
CONECT    8    7    9   15                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10   13                                                       
CONECT   13   12   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13    8   16                                                  
CONECT   16   15   17   24                                                  
CONECT   17   16   18   23                                                  
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20   23                                                       
CONECT   23   22   17                                                       
CONECT   24   16    7   25                                                  
CONECT   25   24   26   32                                                  
CONECT   26   25   27                                                       
CONECT   27   26   28   29                                                  
CONECT   28   27                                                            
CONECT   29   27   30                                                       
CONECT   30   29   31   32                                                  
CONECT   31   30                                                            
CONECT   32   30   25                                                       
CONECT   33    5   34                                                       
CONECT   34   33    2                                                       
MASTER        0    0    0    0    0    0    0    0   34    0   76    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₈H₂₂O₆

Average Mass

454.4780 Da

Monoisotopic Mass

454.14164 Da

IUPAC Name

(1E,2R,3R)-2-(3,5-dihydroxyphenyl)-3-(4-hydroxyphenyl)-1-[(4-hydroxyphenyl)methylidene]-2,3-dihydro-1H-indene-4,6-diol

Traditional Name

(1E,2R,3R)-2-(3,5-dihydroxyphenyl)-3-(4-hydroxyphenyl)-1-[(4-hydroxyphenyl)methylidene]-2,3-dihydroindene-4,6-diol

CAS Registry Number

Not Available

SMILES

OC1=CC=C(\C=C2/[C@H]([C@@H](C3=C(O)C=C(O)C=C23)C2=CC=C(O)C=C2)C2=CC(O)=CC(O)=C2)C=C1

InChI Identifier

InChI=1S/C28H22O6/c29-18-5-1-15(2-6-18)9-23-24-13-22(33)14-25(34)28(24)27(16-3-7-19(30)8-4-16)26(23)17-10-20(31)12-21(32)11-17/h1-14,26-27,29-34H/b23-9-/t26-,27+/m1/s1

InChI Key

BIQMSWPBPAKGSE-PBSLAQMISA-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
Ampelopsis glandulosa	LOTUS Database	35616633
Cissus quadrangularis	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as stilbenes. These are organic compounds containing a 1,2-diphenylethylene moiety. Stilbenes (C6-C2-C6 ) are derived from the common phenylpropene (C6-C3) skeleton building block. The introduction of one or more hydroxyl groups to a phenyl ring lead to stilbenoids.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Stilbenes

Sub Class

Not Available

Direct Parent

Stilbenes

Alternative Parents

Substituents

Stilbene
Indane
Resorcinol
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Phenol
Benzenoid
Monocyclic benzene moiety
Organic oxygen compound
Hydrocarbon derivative
Organooxygen compound
Aromatic homopolycyclic compound

Molecular Framework

Aromatic homopolycyclic compounds

External Descriptors

polyphenol (CHEBI:76192 )
indanes (CHEBI:76192 )
stilbenoid (CHEBI:76192 )

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	4.08	ALOGPS
logP	5.68	ChemAxon
logS	-5.1	ALOGPS
pKa (Strongest Acidic)	8.31	ChemAxon
pKa (Strongest Basic)	-5.5	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	121.38 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	130.21 m³·mol⁻¹	ChemAxon
Polarizability	47.5 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	No	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

C00049739

Chemspider ID

4476724

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Quadrangularin_A

METLIN ID

Not Available

PubChem Compound

5318096

PDB ID

Not Available

ChEBI ID

76192

Good Scents ID

Not Available

References

General References

Avula B, Bae JY, Zhao J, Wang YH, Wang M, Zhang Z, Ali Z, Chittiboyina AG, Khan IA: Quantitative determination and characterization of polyphenols from Cissus quadrangularis L. and dietary supplements using UHPLC-PDA-MS, LC-QToF and HPTLC. J Pharm Biomed Anal. 2021 May 30;199:114036. doi: 10.1016/j.jpba.2021.114036. Epub 2021 Mar 23. [PubMed:33836464 ]
Chitarrini G, Soini E, Riccadonna S, Franceschi P, Zulini L, Masuero D, Vecchione A, Stefanini M, Di Gaspero G, Mattivi F, Vrhovsek U: Identification of Biomarkers for Defense Response to Plasmopara viticola in a Resistant Grape Variety. Front Plant Sci. 2017 Sep 5;8:1524. doi: 10.3389/fpls.2017.01524. eCollection 2017. [PubMed:28928759 ]
Chitarrini G, Zulini L, Masuero D, Vrhovsek U: Lipid, phenol and carotenoid changes in 'Bianca' grapevine leaves after mechanical wounding: a case study. Protoplasma. 2017 Nov;254(6):2095-2106. doi: 10.1007/s00709-017-1100-5. Epub 2017 Mar 21. [PubMed:28324165 ]
Tang ML, Peng P, Liu ZY, Zhang J, Yu JM, Sun X: Sulfoxide-Based Enantioselective Nazarov Cyclization: Divergent Syntheses of (+)-Isopaucifloral F, (+)-Quadrangularin A, and (+)-Pallidol. Chemistry. 2016 Oct 4;22(41):14535-9. doi: 10.1002/chem.201603664. Epub 2016 Aug 30. [PubMed:27490335 ]
Matsuura BS, Keylor MH, Li B, Lin Y, Allison S, Pratt DA, Stephenson CR: A scalable biomimetic synthesis of resveratrol dimers and systematic evaluation of their antioxidant activities. Angew Chem Int Ed Engl. 2015 Mar 16;54(12):3754-7. doi: 10.1002/anie.201409773. Epub 2015 Feb 4. [PubMed:25650836 ]
LOTUS database [Link]

Showing NP-Card for cyphostemmin b (NP0170700)

MOL for NP0170700 (cyphostemmin b)

3D MOL for NP0170700 (cyphostemmin b)

3D SDF for NP0170700 (cyphostemmin b)

3D-SDF for NP0170700 (cyphostemmin b)

PDB for NP0170700 (cyphostemmin b)

3D PDB for NP0170700 (cyphostemmin b)

SMILES for NP0170700 (cyphostemmin b)

INCHI for NP0170700 (cyphostemmin b)

Structure for NP0170700 (cyphostemmin b)

3D Structure for NP0170700 (cyphostemmin b)