NP-MRD: Showing NP-Card for Barbigerone (NP0056541)

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Record Information

Version

2.0

Created at

2022-04-28 02:17:15 UTC

Updated at

2022-04-28 02:17:15 UTC

NP-MRD ID

NP0056541

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Barbigerone

Description

Barbigerone belongs to the class of organic compounds known as pyranoisoflavonoids. These are isoflavonoids that contain a pyran ring fused to either of the A, B, or C ring of the isoflavonoid skeleton. Thus, barbigerone is considered to be a flavonoid lipid molecule. Barbigerone is one of a few pyranoisoflavones among several groups of isoflavones. Barbigerone from S. Globosus is validated to have significant antioxidant property. Members of the genus Millettia are now known to be rich in barbigerone, including M. Dielsiena, M. Ferruginea, M. Usaramensis, and M. Pachycarpa. Barbigerone is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Barbigerone exhibits profound antiplasmodial activity against the malarial parasite Plasmodium falciparum. It was first isolated from the seed of a leguminous plant Tephrosia barbigera; hence the name "barbigerone". It is also demonstrated that it has anti-cancer potential as it causes apoptosis of murine lung-cancer cells. Barbigerone is found in Millettia ferruginea , Millettia pachycarpa, Millettia taiwaniana, Millettia usaramensis, Millettia usaramensis subsp. usaramensis , Sarcolobus globosus and Tephrosia barbigera. It has also been isolated from the medicinal plant Sarcolobus globosus.

Structure

MOL 3D MOL SDF PDB SMILES InChI

  Mrv1533004241517392D          

 29 32  0  0  0  0            999 V2000
   -3.8230   -2.7770    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4105   -2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5855   -2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1730   -1.3480    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3480   -1.3480    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9355   -0.6336    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1105   -0.6336    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9355   -2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3480   -2.7770    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1730   -2.7770    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5855   -3.4914    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4105   -3.4914    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1105   -2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3020   -1.3480    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1270   -1.3480    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5395   -2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645   -2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7770   -1.3480    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6020   -1.3480    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0145   -2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6465   -1.5322    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6465   -2.5928    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6020   -2.7770    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7770   -2.7770    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645   -3.4914    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5395   -3.4914    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1270   -2.7770    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3020   -2.7770    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1105   -3.4914    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  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  1  0  0  0  0
  6  7  1  0  0  0  0
  5  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
  3 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
  8 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  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
 18 19  2  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 20 22  1  0  0  0  0
 20 23  1  0  0  0  0
 23 24  1  0  0  0  0
 17 24  1  0  0  0  0
 24 25  2  0  0  0  0
 25 26  1  0  0  0  0
 26 27  2  0  0  0  0
 16 27  1  0  0  0  0
 27 28  1  0  0  0  0
 13 28  1  0  0  0  0
 28 29  2  0  0  0  0
M  END

     RDKit          3D

 51 54  0  0  0  0  0  0  0  0999 V2000
   -7.6927    0.2924   -0.7558 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4037    0.2413   -0.6489 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1617    0.0643   -0.5335 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5084   -1.1863   -0.3696 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1569   -1.3136   -0.2509 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5581   -2.5610   -0.0914 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3420   -3.7188   -0.0449 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3426   -0.2079   -0.2839 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8907   -0.2495   -0.1795 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0719   -0.9910   -0.9851 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2542   -0.9614   -0.8547 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8639   -0.2248    0.0482 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2353   -0.2118    0.1657 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8718    0.5534    1.1133 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1529    1.3572    2.0041 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7838    1.3231    1.8576 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1146    0.5696    0.9204 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2427    0.5412    0.7898 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9652    1.2315    1.5386 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2318    0.5597    1.2157 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0789   -0.1773    0.3710 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9592    0.8648   -0.3323 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9352   -1.0772    1.2434 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4035   -1.0003   -0.6378 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0846   -0.9992   -0.7140 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9775    1.0336   -0.4448 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2982    1.1718   -0.5635 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8473    2.4335   -0.7221 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0642    3.6004   -0.7671 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0768   -0.2881   -1.6659 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0475    1.3660   -0.9760 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.3167   -0.0446    0.1309 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1821   -2.0283   -0.3461 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7009   -4.0398   -1.0351 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2399   -3.5804    0.6127 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7555   -4.5309    0.4541 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5400   -1.6205   -1.7503 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6643    1.9628    2.7566 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1977    1.9315    2.5300 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0442    1.7964    0.3029 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.9613    0.4242   -0.4215 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5285    1.1519   -1.3202 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3041   -1.4502    2.0560 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2915   -1.8938    0.5765 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7830   -0.4739    1.6163 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9922   -1.5882   -1.3018 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5449   -1.6015   -1.4531 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3114    1.8936   -0.4740 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6304    3.7842    0.2232 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2448    3.4234   -1.5041 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7116    4.4485   -1.0993 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  5  8  2  0
  8 26  1  0
 26 27  2  0
 27 28  1  0
 28 29  1  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
 13 25  1  0
 25 24  2  0
 24 21  1  0
 21 22  1  0
 21 23  1  0
 21 20  1  0
 20 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 27  3  1  0
 18  9  1  0
 17 12  1  0
 14 13  1  0
  1 30  1  0
  1 31  1  0
  1 32  1  0
  4 33  1  0
  7 34  1  0
  7 35  1  0
  7 36  1  0
 26 48  1  0
 29 49  1  0
 29 50  1  0
 29 51  1  0
 10 37  1  0
 25 47  1  0
 24 46  1  0
 22 40  1  0
 22 41  1  0
 22 42  1  0
 23 43  1  0
 23 44  1  0
 23 45  1  0
 15 38  1  0
 16 39  1  0
M  END

  Mrv1533004241517392D          

 29 32  0  0  0  0            999 V2000
   -3.8230   -2.7770    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4105   -2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5855   -2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1730   -1.3480    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3480   -1.3480    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9355   -0.6336    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1105   -0.6336    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9355   -2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3480   -2.7770    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1730   -2.7770    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5855   -3.4914    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4105   -3.4914    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1105   -2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3020   -1.3480    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1270   -1.3480    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5395   -2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645   -2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7770   -1.3480    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6020   -1.3480    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0145   -2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6465   -1.5322    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6465   -2.5928    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6020   -2.7770    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7770   -2.7770    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645   -3.4914    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5395   -3.4914    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1270   -2.7770    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3020   -2.7770    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1105   -3.4914    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  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  1  0  0  0  0
  6  7  1  0  0  0  0
  5  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
  3 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
  8 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  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
 18 19  2  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 20 22  1  0  0  0  0
 20 23  1  0  0  0  0
 23 24  1  0  0  0  0
 17 24  1  0  0  0  0
 24 25  2  0  0  0  0
 25 26  1  0  0  0  0
 26 27  2  0  0  0  0
 16 27  1  0  0  0  0
 27 28  1  0  0  0  0
 13 28  1  0  0  0  0
 28 29  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0056541

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC(OC)=C(C=C1OC)C1=COC2=C3C=CC(C)(C)OC3=CC=C2C1=O

> <INCHI_IDENTIFIER>
InChI=1S/C23H22O6/c1-23(2)9-8-13-17(29-23)7-6-14-21(24)16(12-28-22(13)14)15-10-19(26-4)20(27-5)11-18(15)25-3/h6-12H,1-5H3

> <INCHI_KEY>
OBIUGMGQVQMVSK-UHFFFAOYSA-N

> <FORMULA>
C23H22O6

> <MOLECULAR_WEIGHT>
394.423

> <EXACT_MASS>
394.141638428

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
51

> <JCHEM_AVERAGE_POLARIZABILITY>
42.43549472835282

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
8,8-dimethyl-3-(2,4,5-trimethoxyphenyl)-4H,8H-pyrano[2,3-h]chromen-4-one

> <ALOGPS_LOGP>
4.35

> <JCHEM_LOGP>
3.7651779596666666

> <ALOGPS_LOGS>
-5.32

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-4.254182178670281

> <JCHEM_POLAR_SURFACE_AREA>
63.220000000000006

> <JCHEM_REFRACTIVITY>
109.5232

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.90e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
barbigerone

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 24-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-APR-15         0                                  
HETATM    1  C   UNK     0      -7.136  -5.184   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      -6.366  -3.850   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0      -4.826  -3.850   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -4.056  -2.516   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -2.516  -2.516   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0      -1.746  -1.183   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0      -0.206  -1.183   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -1.746  -3.850   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -2.516  -5.184   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -4.056  -5.184   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      -4.826  -6.517   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0      -6.366  -6.517   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -0.206  -3.850   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       0.564  -2.516   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       2.104  -2.516   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       2.874  -3.850   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       4.414  -3.850   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       5.184  -2.516   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       6.724  -2.516   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       7.494  -3.850   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       8.673  -2.860   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       8.673  -4.840   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       6.724  -5.184   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0       5.184  -5.184   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       4.414  -6.517   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       2.874  -6.517   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       2.104  -5.184   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       0.564  -5.184   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0      -0.206  -6.517   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   10                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6    8                                                  
CONECT    6    5    7                                                       
CONECT    7    6                                                            
CONECT    8    5    9   13                                                  
CONECT    9    8   10                                                       
CONECT   10    9    3   11                                                  
CONECT   11   10   12                                                       
CONECT   12   11                                                            
CONECT   13    8   14   28                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17   27                                                  
CONECT   17   16   18   24                                                  
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21   22   23                                             
CONECT   21   20                                                            
CONECT   22   20                                                            
CONECT   23   20   24                                                       
CONECT   24   23   17   25                                                  
CONECT   25   24   26                                                       
CONECT   26   25   27                                                       
CONECT   27   26   16   28                                                  
CONECT   28   27   13   29                                                  
CONECT   29   28                                                            
MASTER        0    0    0    0    0    0    0    0   29    0   64    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₃H₂₂O₆

Average Mass

394.4230 Da

Monoisotopic Mass

394.14164 Da

IUPAC Name

8,8-dimethyl-3-(2,4,5-trimethoxyphenyl)-4H,8H-pyrano[2,3-h]chromen-4-one

Traditional Name

barbigerone

CAS Registry Number

Not Available

SMILES

COC1=CC(OC)=C(C=C1OC)C1=COC2=C3C=CC(C)(C)OC3=CC=C2C1=O

InChI Identifier

InChI=1S/C23H22O6/c1-23(2)9-8-13-17(29-23)7-6-14-21(24)16(12-28-22(13)14)15-10-19(26-4)20(27-5)11-18(15)25-3/h6-12H,1-5H3

InChI Key

OBIUGMGQVQMVSK-UHFFFAOYSA-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
Millettia ferruginea	Plant	KNApSAcK
Millettia pachycarpa	LOTUS Database	35616633
Millettia taiwaniana	Plant	KNApSAcK
Millettia usaramensis	LOTUS Database	35616633
Millettia usaramensis subsp. usaramensis	Plant	KNApSAcK
Sarcolobus globosus	LOTUS Database	35616633
Tephrosia barbigera	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as pyranoisoflavonoids. These are isoflavonoids that contain a pyran ring fused to either of the A, B, or C ring of the isoflavonoid skeleton.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Isoflavonoids

Sub Class

Pyranoisoflavonoids

Direct Parent

Pyranoisoflavonoids

Alternative Parents

Substituents

Pyranoisoflavonoid
3p-methoxyisoflavone
4p-o-methylisoflavone
Isoflavone
Pyranochromene
2,2-dimethyl-1-benzopyran
Chromone
Benzopyran
1-benzopyran
Phenoxy compound
Anisole
Methoxybenzene
Phenol ether
Alkyl aryl ether
Pyranone
Monocyclic benzene moiety
Benzenoid
Pyran
Heteroaromatic compound
Ether
Organoheterocyclic compound
Oxacycle
Organic oxygen compound
Organic oxide
Organooxygen compound
Hydrocarbon derivative
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Isoflavonoids (LMPK12050076 )

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	4.35	ALOGPS
logP	3.77	ChemAxon
logS	-5.3	ALOGPS
pKa (Strongest Basic)	-4.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	63.22 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	109.52 m³·mol⁻¹	ChemAxon
Polarizability	42.44 Å³	ChemAxon
Number of Rings	4	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

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Barbigerone

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Barbigerone (NP0056541)

MOL for NP0056541 (Barbigerone)

3D MOL for NP0056541 (Barbigerone)

3D SDF for NP0056541 (Barbigerone)

3D-SDF for NP0056541 (Barbigerone)

PDB for NP0056541 (Barbigerone)

3D PDB for NP0056541 (Barbigerone)

SMILES for NP0056541 (Barbigerone)

INCHI for NP0056541 (Barbigerone)

Structure for NP0056541 (Barbigerone)

3D Structure for NP0056541 (Barbigerone)