NP-MRD: Showing NP-Card for (1r,8r,9r)-1,9-bis(3,4-dihydroxyphenyl)-6,8-dihydroxy-1h,2h,7h,8h,9h,10h-naphtho[2,1-b]pyran-3-one (NP0230884)

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Record Information

Version

2.0

Created at

2022-09-06 11:29:36 UTC

Updated at

2022-09-06 11:29:36 UTC

NP-MRD ID

NP0230884

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1r,8r,9r)-1,9-bis(3,4-dihydroxyphenyl)-6,8-dihydroxy-1h,2h,7h,8h,9h,10h-naphtho[2,1-b]pyran-3-one

Description

Cinchonain I a belongs to the class of organic compounds known as prenylated neoflavonoids. These are neoflavonoids that features a C5-isoprenoid substituent at any position of the A, B, or C ring. Neoflavonoids are compounds with a structure based on the 4-phenylchromene backbone. (1r,8r,9r)-1,9-bis(3,4-dihydroxyphenyl)-6,8-dihydroxy-1h,2h,7h,8h,9h,10h-naphtho[2,1-b]pyran-3-one is found in Apocynum venetum, Eriobotrya japonica, Kandelia candel, Trichilia catigua and Uncaria tomentosa. (1r,8r,9r)-1,9-bis(3,4-dihydroxyphenyl)-6,8-dihydroxy-1h,2h,7h,8h,9h,10h-naphtho[2,1-b]pyran-3-one was first documented in 2002 (PMID: 12398535). Based on a literature review very few articles have been published on cinchonain I a (PMID: 26930981).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309062213292D          

 33 37  0  0  1  0            999 V2000
    4.8395    0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0145    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6020   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7770   -0.3020    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.3645   -1.0164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5395   -1.0164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1270   -1.7309    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5395   -2.4454    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1270   -3.1599    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645   -2.4454    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7770   -3.1599    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7770   -1.7309    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7770    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645    1.8414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5395    1.8414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1270    2.5559    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1270    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5395    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1270   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3020   -0.3020    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.1105   -1.0164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3020   -1.7309    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1105   -2.4454    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9355   -2.4454    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3480   -3.1599    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3480   -1.7309    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1730   -1.7309    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9355   -1.0164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1105    0.4125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.9355    0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3020    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6020    1.1270    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  1  0  0  0  0
  4  5  1  6  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  8 10  1  0  0  0  0
 10 11  1  0  0  0  0
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  4 13  1  0  0  0  0
 13 14  2  0  0  0  0
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 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 16 18  1  0  0  0  0
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 19 20  1  0  0  0  0
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 22 23  2  0  0  0  0
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 30 32  1  0  0  0  0
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 14 33  1  0  0  0  0
  2 33  1  0  0  0  0
M  END

     RDKit          3D

 55 59  0  0  0  0  0  0  0  0999 V2000
    4.7814   -2.6801   -2.0530 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5682   -2.5662   -1.7704 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7579   -1.4748   -2.3426 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8739   -0.7801   -1.3235 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.7287    0.2258   -0.6242 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8398   -0.1364    0.1124 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6397    0.7890    0.7442 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3671    2.1301    0.6710 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1819    3.0767    1.3150 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2620    2.5205   -0.0589 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9995    3.8888   -0.1227 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4742    1.5830   -0.6836 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2393   -1.7526   -0.4544 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7923   -3.0287   -0.2772 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2004   -3.9684    0.5718 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0462   -3.6246    1.2462 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5276   -4.5615    2.0815 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4916   -2.3609    1.0625 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0913   -1.4317    0.2243 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5612   -0.1496    0.0910 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0456   -0.4253   -0.2057 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.8226    0.8258   -0.2257 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3967    1.2751   -1.3944 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1338    2.4383   -1.4710 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3136    3.1982   -0.3339 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0373    4.3760   -0.3223 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7517    2.7749    0.8498 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9140    3.5142    2.0062 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0097    1.5939    0.9025 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6704   -1.3650    0.7627 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.7499   -0.7845    1.4516 O   0  0  0  0  0  0  0  0  0  0  0  0
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    2.9421   -3.4527   -0.9162 O   0  0  0  0  0  0  0  0  0  0  0  0
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    4.0556   -1.2001    0.1753 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4946    0.4671    1.3071 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9671    4.0446    1.2497 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2028    4.2266   -0.6440 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6217    1.9573   -1.2447 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6444   -4.9610    0.7002 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0895   -5.4620    2.1730 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5246    0.3676    1.0948 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1925    0.5467   -0.6401 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0450   -0.8554   -1.2469 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2624    0.6836   -2.3018 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5846    2.7902   -2.3910 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4783    4.7395   -1.1756 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4526    4.3664    1.9556 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5733    1.2721    1.8386 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0894   -2.2441    0.1894 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2805   -1.5381    1.8188 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2503   -2.8655    2.1928 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5103   -1.2316    2.5939 H   0  0  0  0  0  0  0  0  0  0  0  0
 31 30  1  0
 30 32  1  0
 32 18  1  0
 18 19  2  0
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 13 14  2  0
 14 33  1  0
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  2  1  2  0
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  3  4  1  0
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 21 30  1  0
 29 22  1  0
  4 13  1  0
 12  5  1  0
 16 18  1  0
 31 53  1  0
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 20 44  1  0
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 23 47  1  0
 24 48  1  0
 26 49  1  0
 28 50  1  0
 29 51  1  0
  3 34  1  0
  3 35  1  0
  4 36  1  6
  6 37  1  0
  7 38  1  0
  9 39  1  0
 11 40  1  0
 12 41  1  0
 15 42  1  0
 17 43  1  0
M  END


  Mrv1652309062213292D          

 33 37  0  0  1  0            999 V2000
    4.8395    0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0145    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6020   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7770   -0.3020    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.3645   -1.0164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5395   -1.0164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1270   -1.7309    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5395   -2.4454    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1270   -3.1599    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645   -2.4454    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7770   -3.1599    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7770   -1.7309    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7770    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645    1.8414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5395    1.8414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1270    2.5559    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1270    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5395    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1270   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3020   -0.3020    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.1105   -1.0164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.9355   -2.4454    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    0.3020    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6020    1.1270    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  1  0  0  0  0
  4  5  1  6  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  8 10  1  0  0  0  0
 10 11  1  0  0  0  0
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 13 14  2  0  0  0  0
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 15 16  2  0  0  0  0
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 18 19  2  0  0  0  0
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 25 26  1  0  0  0  0
 25 27  1  0  0  0  0
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 30 31  1  6  0  0  0
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 14 33  1  0  0  0  0
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M  END
> <DATABASE_ID>
NP0230884

> <DATABASE_NAME>
NP-MRD

> <SMILES>
O[C@@H]1CC2=C(C[C@@H]1C1=CC=C(O)C(O)=C1)C1=C(OC(=O)C[C@@H]1C1=CC=C(O)C(O)=C1)C=C2O

> <INCHI_IDENTIFIER>
InChI=1S/C25H22O8/c26-17-3-1-11(5-21(17)30)13-7-16-15(8-19(13)28)20(29)10-23-25(16)14(9-24(32)33-23)12-2-4-18(27)22(31)6-12/h1-6,10,13-14,19,26-31H,7-9H2/t13-,14-,19-/m1/s1

> <INCHI_KEY>
DKTDHUGOEJFFSN-PJIJBLCYSA-N

> <FORMULA>
C25H22O8

> <MOLECULAR_WEIGHT>
450.443

> <EXACT_MASS>
450.131467668

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
55

> <JCHEM_AVERAGE_POLARIZABILITY>
45.07967844305948

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
6

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1R,8R,9R)-1,9-bis(3,4-dihydroxyphenyl)-6,8-dihydroxy-1H,2H,3H,7H,8H,9H,10H-naphtho[2,1-b]pyran-3-one

> <JCHEM_LOGP>
3.353478397666667

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.282551928074414

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.795886335302432

> <JCHEM_PKA_STRONGEST_BASIC>
-2.936002162964888

> <JCHEM_POLAR_SURFACE_AREA>
147.68

> <JCHEM_REFRACTIVITY>
118.72170000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(1R,8R,9R)-1,9-bis(3,4-dihydroxyphenyl)-6,8-dihydroxy-1H,2H,7H,8H,9H,10H-naphtho[2,1-b]pyran-3-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 06-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-SEP-22         0                                  
HETATM    1  O   UNK     0       9.034   0.770   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       7.494   0.770   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       6.724  -0.564   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       5.184  -0.564   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       4.414  -1.897   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.874  -1.897   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.104  -3.231   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.874  -4.565   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       2.104  -5.898   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       4.414  -4.565   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       5.184  -5.898   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       5.184  -3.231   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.414   0.770   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       5.184   2.104   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.414   3.437   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       2.874   3.437   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       2.104   4.771   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       2.104   2.104   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       2.874   0.770   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       2.104  -0.564   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       0.564  -0.564   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -0.206  -1.897   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       0.564  -3.231   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      -0.206  -4.565   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      -1.746  -4.565   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0      -2.516  -5.898   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0      -2.516  -3.231   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0      -4.056  -3.231   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0      -1.746  -1.897   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      -0.206   0.770   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0      -1.746   0.770   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0       0.564   2.104   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0       6.724   2.104   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   33                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5   13                                                  
CONECT    5    4    6   12                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10    5                                                       
CONECT   13    4   14   19                                                  
CONECT   14   13   15   33                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16   19   32                                                  
CONECT   19   18   13   20                                                  
CONECT   20   19   21                                                       
CONECT   21   20   22   30                                                  
CONECT   22   21   23   29                                                  
CONECT   23   22   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24   26   27                                                  
CONECT   26   25                                                            
CONECT   27   25   28   29                                                  
CONECT   28   27                                                            
CONECT   29   27   22                                                       
CONECT   30   21   31   32                                                  
CONECT   31   30                                                            
CONECT   32   30   18                                                       
CONECT   33   14    2                                                       
MASTER        0    0    0    0    0    0    0    0   33    0   74    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₅H₂₂O₈

Average Mass

450.4430 Da

Monoisotopic Mass

450.13147 Da

IUPAC Name

(1R,8R,9R)-1,9-bis(3,4-dihydroxyphenyl)-6,8-dihydroxy-1H,2H,3H,7H,8H,9H,10H-naphtho[2,1-b]pyran-3-one

Traditional Name

(1R,8R,9R)-1,9-bis(3,4-dihydroxyphenyl)-6,8-dihydroxy-1H,2H,7H,8H,9H,10H-naphtho[2,1-b]pyran-3-one

CAS Registry Number

Not Available

SMILES

O[C@@H]1CC2=C(C[C@@H]1C1=CC=C(O)C(O)=C1)C1=C(OC(=O)C[C@@H]1C1=CC=C(O)C(O)=C1)C=C2O

InChI Identifier

InChI=1S/C25H22O8/c26-17-3-1-11(5-21(17)30)13-7-16-15(8-19(13)28)20(29)10-23-25(16)14(9-24(32)33-23)12-2-4-18(27)22(31)6-12/h1-6,10,13-14,19,26-31H,7-9H2/t13-,14-,19-/m1/s1

InChI Key

DKTDHUGOEJFFSN-PJIJBLCYSA-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
Apocynum venetum	LOTUS Database	35616633
Eriobotrya japonica	LOTUS Database	35616633
Kandelia candel	LOTUS Database	35616633
Trichilia catigua	LOTUS Database	35616633
Uncaria tomentosa	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as prenylated neoflavonoids. These are neoflavonoids that features a C5-isoprenoid substituent at any position of the A, B, or C ring. Neoflavonoids are compounds with a structure based on the 4-phenylchromene backbone.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Neoflavonoids

Sub Class

Prenylated neoflavonoids

Direct Parent

Prenylated neoflavonoids

Alternative Parents

Substituents

Prenylated neoflavonoid
Linear 1,7-diphenylheptane skeleton
Neoflavan
Phenylnaphthalene
Naphthopyranone
Naphthopyran
3,4-dihydrocoumarin
Chromane
Benzopyran
1-benzopyran
Tetralin
Naphthalene
Catechol
1-hydroxy-2-unsubstituted benzenoid
1-hydroxy-4-unsubstituted benzenoid
Phenol
Monocyclic benzene moiety
Benzenoid
Pyran
Carboxylic acid ester
Secondary alcohol
Lactone
Carboxylic acid derivative
Organoheterocyclic compound
Oxacycle
Monocarboxylic acid or derivatives
Organic oxide
Organic oxygen compound
Carbonyl group
Hydrocarbon derivative
Alcohol
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	3.35	ChemAxon
pKa (Strongest Acidic)	8.8	ChemAxon
pKa (Strongest Basic)	-2.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	147.68 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	118.72 m³·mol⁻¹	ChemAxon
Polarizability	45.08 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	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

24704758

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

44575965

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Xiang MX, Hu YJ, He F, Liu XQ: [Chemical Composition of n-Butanol Fraction from Polygonum amplexicaule var. sinense]. Zhong Yao Cai. 2015 Sep;38(9):1872-4. [PubMed:26930981 ]
Ming DS, Lopez A, Hillhouse BJ, French CJ, Hudson JB, Towers GH: Bioactive constituents from Iryanthera megistophylla. J Nat Prod. 2002 Oct;65(10):1412-6. doi: 10.1021/np020169l. [PubMed:12398535 ]
LOTUS database [Link]

Showing NP-Card for (1r,8r,9r)-1,9-bis(3,4-dihydroxyphenyl)-6,8-dihydroxy-1h,2h,7h,8h,9h,10h-naphtho[2,1-b]pyran-3-one (NP0230884)

MOL for NP0230884 ((1r,8r,9r)-1,9-bis(3,4-dihydroxyphenyl)-6,8-dihydroxy-1h,2h,7h,8h,9h,10h-naphtho[2,1-b]pyran-3-one)

3D MOL for NP0230884 ((1r,8r,9r)-1,9-bis(3,4-dihydroxyphenyl)-6,8-dihydroxy-1h,2h,7h,8h,9h,10h-naphtho[2,1-b]pyran-3-one)

3D SDF for NP0230884 ((1r,8r,9r)-1,9-bis(3,4-dihydroxyphenyl)-6,8-dihydroxy-1h,2h,7h,8h,9h,10h-naphtho[2,1-b]pyran-3-one)

3D-SDF for NP0230884 ((1r,8r,9r)-1,9-bis(3,4-dihydroxyphenyl)-6,8-dihydroxy-1h,2h,7h,8h,9h,10h-naphtho[2,1-b]pyran-3-one)

PDB for NP0230884 ((1r,8r,9r)-1,9-bis(3,4-dihydroxyphenyl)-6,8-dihydroxy-1h,2h,7h,8h,9h,10h-naphtho[2,1-b]pyran-3-one)

3D PDB for NP0230884 ((1r,8r,9r)-1,9-bis(3,4-dihydroxyphenyl)-6,8-dihydroxy-1h,2h,7h,8h,9h,10h-naphtho[2,1-b]pyran-3-one)

SMILES for NP0230884 ((1r,8r,9r)-1,9-bis(3,4-dihydroxyphenyl)-6,8-dihydroxy-1h,2h,7h,8h,9h,10h-naphtho[2,1-b]pyran-3-one)

INCHI for NP0230884 ((1r,8r,9r)-1,9-bis(3,4-dihydroxyphenyl)-6,8-dihydroxy-1h,2h,7h,8h,9h,10h-naphtho[2,1-b]pyran-3-one)

Structure for NP0230884 ((1r,8r,9r)-1,9-bis(3,4-dihydroxyphenyl)-6,8-dihydroxy-1h,2h,7h,8h,9h,10h-naphtho[2,1-b]pyran-3-one)

3D Structure for NP0230884 ((1r,8r,9r)-1,9-bis(3,4-dihydroxyphenyl)-6,8-dihydroxy-1h,2h,7h,8h,9h,10h-naphtho[2,1-b]pyran-3-one)