NP-MRD: Showing NP-Card for Lithospermic acid B (NP0072212)

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Record Information

Version

1.0

Created at

2022-04-28 17:34:51 UTC

Updated at

2022-04-28 17:34:51 UTC

NP-MRD ID

NP0072212

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Lithospermic acid B

Description

(2R)-2-{[(2E)-3-[(2S,3S)-3-{[(1R)-1-carboxy-2-(3,4-dihydroxyphenyl)ethoxy]carbonyl}-2-(3,4-dihydroxyphenyl)-7-hydroxy-2,3-dihydro-1-benzofuran-4-yl]prop-2-enoyl]oxy}-3-(3,4-dihydroxyphenyl)propanoic acid belongs to the class of organic compounds known as 2-arylbenzofuran flavonoids. Lithospermic acid B is found in Celastrus hindsii, Lithospermum erythrorhizon , Meehania fargesii, Meehania urticifolia, Origanum vulgare , Orthosiphon stamineus , Pseudostellaria heterophylla, Salvia bowleyana, Salvia cavaleriei, Salvia chinensis, Salvia deserta, Salvia flava , Salvia militorrhiza, Salvia miltiorhiza, Salvia miltiorrihiza, Salvia prionitis , Salvia przewalskii, Salvia sonchifolia, Salvia yunnanensis and Salviae miltiorrhizae. These are phenylpropanoids containing the 2-phenylbenzofuran moiety (2R)-2-{[(2E)-3-[(2S,3S)-3-{[(1R)-1-carboxy-2-(3,4-dihydroxyphenyl)ethoxy]carbonyl}-2-(3,4-dihydroxyphenyl)-7-hydroxy-2,3-dihydro-1-benzofuran-4-yl]prop-2-enoyl]oxy}-3-(3,4-dihydroxyphenyl)propanoic acid is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI

6451084
  Mrv0541 02271202152D          

 52 56  0  0  1  0            999 V2000
    6.0032   -3.7577    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7085   -1.0316    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.0667   -1.4755    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080   -4.7439    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.9597   -4.5227    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.7847   -3.0938    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0790    0.2063    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.0283    0.7069    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.3230   -0.6914    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080    0.2063    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.5409    2.2752    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4389    3.5034    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935    2.2688    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080    1.0313    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935    3.9188    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645    4.7439    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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  1 18  1  0  0  0  0
  1 20  1  0  0  0  0
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 48 50  1  0  0  0  0
 49 51  2  0  0  0  0
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 51 52  1  0  0  0  0
M  END

     RDKit          3D

 82 86  0  0  0  0  0  0  0  0999 V2000
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M  END

6451084
  Mrv0541 02271202152D          

 52 56  0  0  1  0            999 V2000
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    8.9597   -4.5227    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.7847   -3.0938    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0790    0.2063    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.0283    0.7069    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.3230   -0.6914    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080    0.2063    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.5409    2.2752    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4389    3.5034    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935    2.2688    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080    1.0313    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935    3.9188    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645    4.7439    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0032   -2.4299    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.4846   -3.0938    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.2224   -2.6813    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2224   -3.5063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3097   -3.0938    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080   -2.2688    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2594   -1.6457    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080   -3.9188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935   -2.6813    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7222   -3.8083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7222   -2.3794    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935   -3.5063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080   -1.4438    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9647   -0.2474    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    8.5472   -3.8083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5472   -2.3794    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4138    0.3666    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9597   -3.0938    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935   -1.0313    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6700    1.1508    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7720   -0.0773    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935   -0.2063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4774    1.3209    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1191    1.7649    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0790    1.0313    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.3645    1.4438    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7336    2.1051    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3754    2.5491    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1827    2.7192    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645    2.2688    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935    1.4438    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0790    2.6813    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500    2.6813    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0790    3.5063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500    3.5063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645    3.9188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1 18  1  0  0  0  0
  1 20  1  0  0  0  0
  2 23  1  0  0  0  0
 30  2  1  6  0  0  0
  3 23  2  0  0  0  0
  4 24  1  0  0  0  0
  5 31  1  0  0  0  0
  6 34  1  0  0  0  0
  7 38  1  0  0  0  0
 41  7  1  6  0  0  0
  8 37  1  0  0  0  0
  9 37  2  0  0  0  0
 10 38  2  0  0  0  0
 11 43  1  0  0  0  0
 12 45  1  0  0  0  0
 13 47  1  0  0  0  0
 14 47  2  0  0  0  0
 15 50  1  0  0  0  0
 16 52  1  0  0  0  0
 17 18  1  0  0  0  0
 17 19  1  0  0  0  0
 17 23  1  6  0  0  0
 18 21  1  1  0  0  0
 19 20  1  0  0  0  0
 19 22  2  0  0  0  0
 20 24  2  0  0  0  0
 21 26  2  0  0  0  0
 21 27  1  0  0  0  0
 22 25  1  0  0  0  0
 22 29  1  0  0  0  0
 24 28  1  0  0  0  0
 25 28  2  0  0  0  0
 26 31  1  0  0  0  0
 27 32  2  0  0  0  0
 29 35  2  0  0  0  0
 30 33  1  0  0  0  0
 30 37  1  0  0  0  0
 31 34  2  0  0  0  0
 32 34  1  0  0  0  0
 33 36  1  0  0  0  0
 35 38  1  0  0  0  0
 36 39  2  0  0  0  0
 36 40  1  0  0  0  0
 39 43  1  0  0  0  0
 40 44  2  0  0  0  0
 41 42  1  0  0  0  0
 41 47  1  0  0  0  0
 42 46  1  0  0  0  0
 43 45  2  0  0  0  0
 44 45  1  0  0  0  0
 46 48  2  0  0  0  0
 46 49  1  0  0  0  0
 48 50  1  0  0  0  0
 49 51  2  0  0  0  0
 50 52  2  0  0  0  0
 51 52  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0072212

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC(=O)[C@@H](CC1=CC(O)=C(O)C=C1)OC(=O)\C=C\C1=C2[C@@H]([C@H](OC2=C(O)C=C1)C1=CC(O)=C(O)C=C1)C(=O)O[C@H](CC1=CC(O)=C(O)C=C1)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C36H30O16/c37-20-6-1-16(11-24(20)41)13-27(34(45)46)50-29(44)10-5-18-3-9-23(40)33-30(18)31(32(52-33)19-4-8-22(39)26(43)15-19)36(49)51-28(35(47)48)14-17-2-7-21(38)25(42)12-17/h1-12,15,27-28,31-32,37-43H,13-14H2,(H,45,46)(H,47,48)/b10-5+/t27-,28-,31+,32-/m1/s1

> <INCHI_KEY>
SNKFFCBZYFGCQN-VWUOOIFGSA-N

> <FORMULA>
C36H30O16

> <MOLECULAR_WEIGHT>
718.6138

> <EXACT_MASS>
718.153384912

> <JCHEM_ACCEPTOR_COUNT>
14

> <JCHEM_AVERAGE_POLARIZABILITY>
69.67680995056233

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
9

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2R)-2-{[(2E)-3-[(2S,3S)-3-{[(1R)-1-carboxy-2-(3,4-dihydroxyphenyl)ethoxy]carbonyl}-2-(3,4-dihydroxyphenyl)-7-hydroxy-2,3-dihydro-1-benzofuran-4-yl]prop-2-enoyl]oxy}-3-(3,4-dihydroxyphenyl)propanoic acid

> <ALOGPS_LOGP>
3.93

> <JCHEM_LOGP>
4.987507691666666

> <ALOGPS_LOGS>
-4.51

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
3.3760629515410283

> <JCHEM_PKA_STRONGEST_ACIDIC>
2.7735696234380063

> <JCHEM_PKA_STRONGEST_BASIC>
-5.107139298486509

> <JCHEM_POLAR_SURFACE_AREA>
278.04

> <JCHEM_REFRACTIVITY>
177.00089999999994

> <JCHEM_ROTATABLE_BOND_COUNT>
14

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.23e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2R)-2-{[(2E)-3-[(2S,3S)-3-{[(1R)-1-carboxy-2-(3,4-dihydroxyphenyl)ethoxy]carbonyl}-2-(3,4-dihydroxyphenyl)-7-hydroxy-2,3-dihydro-1-benzofuran-4-yl]prop-2-enoyl]oxy}-3-(3,4-dihydroxyphenyl)propanoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 27-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 6451084                                           
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-FEB-12         0                                  
HETATM    1  O   UNK     0      11.206  -7.014   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0      10.656  -1.926   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0      13.191  -2.754   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0       8.415  -8.855   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0      16.725  -8.442   0.000  0.00  0.00           O+0
HETATM    6  O   UNK     0      18.265  -5.775   0.000  0.00  0.00           O+0
HETATM    7  O   UNK     0       5.747   0.385   0.000  0.00  0.00           O+0
HETATM    8  O   UNK     0      13.119   1.320   0.000  0.00  0.00           O+0
HETATM    9  O   UNK     0      13.670  -1.291   0.000  0.00  0.00           O+0
HETATM   10  O   UNK     0       8.415   0.385   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0      14.076   4.247   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0      12.019   6.540   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0       7.081   4.235   0.000  0.00  0.00           O+0
HETATM   14  O   UNK     0       8.415   1.925   0.000  0.00  0.00           O+0
HETATM   15  O   UNK     0       7.081   7.315   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0       4.414   8.855   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0      11.206  -4.536   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      12.105  -5.775   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       9.748  -5.005   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       9.748  -6.545   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      13.645  -5.775   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       8.415  -4.235   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      11.684  -3.072   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       8.415  -7.315   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       7.081  -5.005   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      14.415  -7.109   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      14.415  -4.442   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       7.081  -6.545   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       8.415  -2.695   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      11.134  -0.462   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      15.955  -7.109   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      15.955  -4.442   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      10.106   0.684   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      16.725  -5.775   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       7.081  -1.925   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      10.584   2.148   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0      12.641  -0.144   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0       7.081  -0.385   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0      12.091   2.466   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0       9.556   3.294   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0       5.747   1.925   0.000  0.00  0.00           C+0
HETATM   42  C   UNK     0       4.414   2.695   0.000  0.00  0.00           C+0
HETATM   43  C   UNK     0      12.569   3.930   0.000  0.00  0.00           C+0
HETATM   44  C   UNK     0      10.034   4.758   0.000  0.00  0.00           C+0
HETATM   45  C   UNK     0      11.541   5.076   0.000  0.00  0.00           C+0
HETATM   46  C   UNK     0       4.414   4.235   0.000  0.00  0.00           C+0
HETATM   47  C   UNK     0       7.081   2.695   0.000  0.00  0.00           C+0
HETATM   48  C   UNK     0       5.747   5.005   0.000  0.00  0.00           C+0
HETATM   49  C   UNK     0       3.080   5.005   0.000  0.00  0.00           C+0
HETATM   50  C   UNK     0       5.747   6.545   0.000  0.00  0.00           C+0
HETATM   51  C   UNK     0       3.080   6.545   0.000  0.00  0.00           C+0
HETATM   52  C   UNK     0       4.414   7.315   0.000  0.00  0.00           C+0
CONECT    1   18   20                                                       
CONECT    2   23   30                                                       
CONECT    3   23                                                            
CONECT    4   24                                                            
CONECT    5   31                                                            
CONECT    6   34                                                            
CONECT    7   38   41                                                       
CONECT    8   37                                                            
CONECT    9   37                                                            
CONECT   10   38                                                            
CONECT   11   43                                                            
CONECT   12   45                                                            
CONECT   13   47                                                            
CONECT   14   47                                                            
CONECT   15   50                                                            
CONECT   16   52                                                            
CONECT   17   18   19   23                                                  
CONECT   18    1   17   21                                                  
CONECT   19   17   20   22                                                  
CONECT   20    1   19   24                                                  
CONECT   21   18   26   27                                                  
CONECT   22   19   25   29                                                  
CONECT   23    2    3   17                                                  
CONECT   24    4   20   28                                                  
CONECT   25   22   28                                                       
CONECT   26   21   31                                                       
CONECT   27   21   32                                                       
CONECT   28   24   25                                                       
CONECT   29   22   35                                                       
CONECT   30    2   33   37                                                  
CONECT   31    5   26   34                                                  
CONECT   32   27   34                                                       
CONECT   33   30   36                                                       
CONECT   34    6   31   32                                                  
CONECT   35   29   38                                                       
CONECT   36   33   39   40                                                  
CONECT   37    8    9   30                                                  
CONECT   38    7   10   35                                                  
CONECT   39   36   43                                                       
CONECT   40   36   44                                                       
CONECT   41    7   42   47                                                  
CONECT   42   41   46                                                       
CONECT   43   11   39   45                                                  
CONECT   44   40   45                                                       
CONECT   45   12   43   44                                                  
CONECT   46   42   48   49                                                  
CONECT   47   13   14   41                                                  
CONECT   48   46   50                                                       
CONECT   49   46   51                                                       
CONECT   50   15   48   52                                                  
CONECT   51   49   52                                                       
CONECT   52   16   50   51                                                  
MASTER        0    0    0    0    0    0    0    0   52    0  112    0
END

View in JSmol

Synonyms

Value	Source
(2R)-2-{[(2E)-3-[(2S,3S)-3-{[(1R)-1-carboxy-2-(3,4-dihydroxyphenyl)ethoxy]carbonyl}-2-(3,4-dihydroxyphenyl)-7-hydroxy-2,3-dihydro-1-benzofuran-4-yl]prop-2-enoyl]oxy}-3-(3,4-dihydroxyphenyl)propanoate	Generator
Monardic acid b	MeSH
Salvianolic acid b	MeSH
Salvianolate b	Generator

Chemical Formula

C₃₆H₃₀O₁₆

Average Mass

718.6138 Da

Monoisotopic Mass

718.15338 Da

IUPAC Name

Traditional Name

CAS Registry Number

Not Available

SMILES

OC(=O)[C@@H](CC1=CC(O)=C(O)C=C1)OC(=O)\C=C\C1=C2[C@@H]([C@H](OC2=C(O)C=C1)C1=CC(O)=C(O)C=C1)C(=O)O[C@H](CC1=CC(O)=C(O)C=C1)C(O)=O

InChI Identifier

InChI=1S/C36H30O16/c37-20-6-1-16(11-24(20)41)13-27(34(45)46)50-29(44)10-5-18-3-9-23(40)33-30(18)31(32(52-33)19-4-8-22(39)26(43)15-19)36(49)51-28(35(47)48)14-17-2-7-21(38)25(42)12-17/h1-12,15,27-28,31-32,37-43H,13-14H2,(H,45,46)(H,47,48)/b10-5+/t27-,28-,31+,32-/m1/s1

InChI Key

SNKFFCBZYFGCQN-VWUOOIFGSA-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
Celastrus hindsii	LOTUS Database	35616633
Lithospermum erythrorhizon	Plant	KNApSAcK
Meehania fargesii	LOTUS Database	35616633
Meehania urticifolia	LOTUS Database	35616633
Origanum vulgare	Plant	KNApSAcK
Orthosiphon stamineus	Plant	KNApSAcK
Pseudostellaria heterophylla	LOTUS Database	35616633
Salvia bowleyana	Plant	KNApSAcK
Salvia cavaleriei	Plant	KNApSAcK
Salvia chinensis	Plant	KNApSAcK
Salvia deserta	LOTUS Database	35616633
Salvia flava	Plant	KNApSAcK
Salvia militorrhiza	Plant	KNApSAcK
Salvia miltiorrhiza	Plant	KNApSAcK
Salvia miltiorrihiza	Plant	KNApSAcK
Salvia prionitis	Plant	KNApSAcK
Salvia przewalskii	LOTUS Database	35616633
Salvia sonchifolia	Plant	KNApSAcK
Salvia Yunnanensis	Plant	KNApSAcK
Salviae miltiorrhizae	-	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 2-arylbenzofuran flavonoids. These are phenylpropanoids containing the 2-phenylbenzofuran moiety.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

2-arylbenzofuran flavonoids

Sub Class

Not Available

Direct Parent

2-arylbenzofuran flavonoids

Alternative Parents

Substituents

2-arylbenzofuran flavonoid
Tetracarboxylic acid or derivatives
Cinnamic acid or derivatives
Coumaric acid or derivatives
Cinnamic acid ester
3-phenylpropanoic-acid
Coumaran
Catechol
Styrene
Alkyl aryl ether
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Phenol
Fatty acid ester
Benzenoid
Fatty acyl
Monocyclic benzene moiety
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Carboxylic acid ester
Ether
Carboxylic acid
Oxacycle
Carboxylic acid derivative
Organoheterocyclic compound
Organic oxygen compound
Organic oxide
Carbonyl group
Hydrocarbon derivative
Organooxygen compound
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	3.93	ALOGPS
logP	4.99	ChemAxon
logS	-4.5	ALOGPS
pKa (Strongest Acidic)	2.77	ChemAxon
pKa (Strongest Basic)	-5.1	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	14	ChemAxon
Hydrogen Donor Count	9	ChemAxon
Polar Surface Area	278.04 Å²	ChemAxon
Rotatable Bond Count	14	ChemAxon
Refractivity	177 m³·mol⁻¹	ChemAxon
Polarizability	69.68 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	Yes	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

Not Available

METLIN ID

Not Available

PubChem Compound

6451084

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Lithospermic acid B (NP0072212)

MOL for NP0072212 (Lithospermic acid B)

3D MOL for NP0072212 (Lithospermic acid B)

3D SDF for NP0072212 (Lithospermic acid B)

3D-SDF for NP0072212 (Lithospermic acid B)

PDB for NP0072212 (Lithospermic acid B)

3D PDB for NP0072212 (Lithospermic acid B)

SMILES for NP0072212 (Lithospermic acid B)

INCHI for NP0072212 (Lithospermic acid B)

Structure for NP0072212 (Lithospermic acid B)

3D Structure for NP0072212 (Lithospermic acid B)