NP-MRD: Showing NP-Card for 8-epi-grandifloric acid (NP0028367)

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Record Information

Version

2.0

Created at

2021-06-19 20:16:31 UTC

Updated at

2021-06-29 23:55:07 UTC

NP-MRD ID

NP0028367

Secondary Accession Numbers

None

Natural Product Identification

Common Name

8-epi-grandifloric acid

Provided By

JEOL Database JEOL Logo

Description

8-epi-grandifloric acid is found in Thunbergia laurifolia. 8-epi-grandifloric acid was first documented in 2002 (Kanchanapoom, T., et al.).

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306192122163D          

 46 48  0  0  0  0            999 V2000
    1.1715    1.0275    4.5116 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2235    1.5569    3.9545 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9496    0.9141    3.7950 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2441    2.9186    3.3055 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.9687    3.7892    3.6785 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.6474    4.1490    2.3624 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.5038    4.1348    1.3521 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.9629    4.0771   -0.0665 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7639    2.9932   -0.8221 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2154    1.8192   -0.3875 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2026    1.6500    1.0402 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.6403    0.5540    1.4007 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1429   -0.7039    0.9442 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7961   -1.0250   -0.2853 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4094   -2.2882   -0.8255 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.1310   -2.4620   -2.1687 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.8350   -3.7311   -2.7481 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7535   -3.4288    0.1475 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.2786   -4.7034   -0.3038 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1022   -3.1521    1.5014 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.5116   -4.1376    2.4642 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4612   -1.7628    2.0237 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.2783   -1.5418    3.2489 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3248    2.9091    1.7605 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.7170   -0.0414    3.9352 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1355    3.4269    3.6992 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6153    4.7074    4.1645 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6676    3.3114    4.3721 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4118    3.4013    2.1176 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1428    5.1240    2.4152 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1078    5.0371    1.4876 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4106    4.9658   -0.5021 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9969    2.9453   -1.8784 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2311    1.4340    1.3584 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9434   -0.6561    0.7890 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6712   -2.2918   -1.0231 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8231   -1.6730   -2.8639 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2160   -2.3795   -2.0394 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2392   -3.7277   -3.6364 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8394   -3.5135    0.2776 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4627   -4.7400   -1.2697 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9881   -3.2555    1.4273 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4311   -4.9937    1.9942 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5235   -1.7188    2.2940 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0784   -2.3452    3.7793 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3714    3.0550    1.4580 H   0  0  0  0  0  0  0  0  0  0  0  0
 22 20  1  0  0  0  0
 20 18  1  0  0  0  0
  7  6  1  0  0  0  0
  6  5  1  0  0  0  0
  5  4  1  0  0  0  0
  4 24  1  0  0  0  0
  7 24  1  0  0  0  0
 18 15  1  0  0  0  0
 15 14  1  0  0  0  0
 14 13  1  0  0  0  0
 18 19  1  0  0  0  0
 20 21  1  0  0  0  0
  7  8  1  0  0  0  0
 24 11  1  0  0  0  0
 11 10  1  0  0  0  0
 10  9  1  0  0  0  0
  9  8  2  0  0  0  0
 22 23  1  0  0  0  0
  4  2  1  0  0  0  0
 11 12  1  0  0  0  0
 24 46  1  1  0  0  0
  7 31  1  6  0  0  0
 16 17  1  0  0  0  0
  2  1  2  0  0  0  0
 13 22  1  0  0  0  0
  2  3  1  0  0  0  0
 15 16  1  0  0  0  0
 13 12  1  0  0  0  0
 13 35  1  6  0  0  0
 18 40  1  1  0  0  0
 19 41  1  0  0  0  0
 20 42  1  6  0  0  0
 21 43  1  0  0  0  0
 22 44  1  1  0  0  0
 23 45  1  0  0  0  0
 16 37  1  0  0  0  0
 16 38  1  0  0  0  0
 15 36  1  6  0  0  0
 17 39  1  0  0  0  0
  6 29  1  0  0  0  0
  6 30  1  0  0  0  0
  5 27  1  0  0  0  0
  5 28  1  0  0  0  0
  4 26  1  1  0  0  0
 11 34  1  1  0  0  0
  9 33  1  0  0  0  0
  8 32  1  0  0  0  0
  3 25  1  0  0  0  0
M  END

     RDKit          3D

 46 48  0  0  0  0  0  0  0  0999 V2000
    1.1715    1.0275    4.5116 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2235    1.5569    3.9545 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9496    0.9141    3.7950 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2441    2.9186    3.3055 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.9687    3.7892    3.6785 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6474    4.1490    2.3624 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5038    4.1348    1.3521 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.9629    4.0771   -0.0665 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7639    2.9932   -0.8221 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2154    1.8192   -0.3875 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2026    1.6500    1.0402 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.6403    0.5540    1.4007 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1429   -0.7039    0.9442 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7961   -1.0250   -0.2853 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4094   -2.2882   -0.8255 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.1310   -2.4620   -2.1687 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8350   -3.7311   -2.7481 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7535   -3.4288    0.1475 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.2786   -4.7034   -0.3038 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1022   -3.1521    1.5014 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.5116   -4.1376    2.4642 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4612   -1.7628    2.0237 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.2783   -1.5418    3.2489 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3248    2.9091    1.7605 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.7170   -0.0414    3.9352 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1355    3.4269    3.6992 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6153    4.7074    4.1645 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6676    3.3114    4.3721 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4118    3.4013    2.1176 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1428    5.1240    2.4152 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1078    5.0371    1.4876 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4106    4.9658   -0.5021 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9969    2.9453   -1.8784 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2311    1.4340    1.3584 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9434   -0.6561    0.7890 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6712   -2.2918   -1.0231 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8231   -1.6730   -2.8639 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2160   -2.3795   -2.0394 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2392   -3.7277   -3.6364 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8394   -3.5135    0.2776 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4627   -4.7400   -1.2697 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9881   -3.2555    1.4273 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4311   -4.9937    1.9942 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5235   -1.7188    2.2940 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0784   -2.3452    3.7793 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3714    3.0550    1.4580 H   0  0  0  0  0  0  0  0  0  0  0  0
 22 20  1  0
 20 18  1  0
  7  6  1  0
  6  5  1  0
  5  4  1  0
  4 24  1  0
  7 24  1  0
 18 15  1  0
 15 14  1  0
 14 13  1  0
 18 19  1  0
 20 21  1  0
  7  8  1  0
 24 11  1  0
 11 10  1  0
 10  9  1  0
  9  8  2  0
 22 23  1  0
  4  2  1  0
 11 12  1  0
 24 46  1  1
  7 31  1  6
 16 17  1  0
  2  1  2  0
 13 22  1  0
  2  3  1  0
 15 16  1  0
 13 12  1  0
 13 35  1  6
 18 40  1  1
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 21 43  1  0
 22 44  1  1
 23 45  1  0
 16 37  1  0
 16 38  1  0
 15 36  1  6
 17 39  1  0
  6 29  1  0
  6 30  1  0
  5 27  1  0
  5 28  1  0
  4 26  1  1
 11 34  1  1
  9 33  1  0
  8 32  1  0
  3 25  1  0
M  END


  Mrv1652306192122163D          

 46 48  0  0  0  0            999 V2000
    1.1715    1.0275    4.5116 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2235    1.5569    3.9545 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9496    0.9141    3.7950 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2441    2.9186    3.3055 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.9687    3.7892    3.6785 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.6474    4.1490    2.3624 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.5038    4.1348    1.3521 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.9629    4.0771   -0.0665 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7639    2.9932   -0.8221 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2154    1.8192   -0.3875 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2026    1.6500    1.0402 C   0  0  1  0  0  0  0  0  0  0  0  0
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    0.7961   -1.0250   -0.2853 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4094   -2.2882   -0.8255 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.1310   -2.4620   -2.1687 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.8350   -3.7311   -2.7481 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7535   -3.4288    0.1475 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.2786   -4.7034   -0.3038 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1022   -3.1521    1.5014 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.5116   -4.1376    2.4642 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4612   -1.7628    2.0237 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.2783   -1.5418    3.2489 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3248    2.9091    1.7605 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.7170   -0.0414    3.9352 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1355    3.4269    3.6992 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.9969    2.9453   -1.8784 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.0784   -2.3452    3.7793 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3714    3.0550    1.4580 H   0  0  0  0  0  0  0  0  0  0  0  0
 22 20  1  0  0  0  0
 20 18  1  0  0  0  0
  7  6  1  0  0  0  0
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  5  4  1  0  0  0  0
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 18 19  1  0  0  0  0
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  7  8  1  0  0  0  0
 24 11  1  0  0  0  0
 11 10  1  0  0  0  0
 10  9  1  0  0  0  0
  9  8  2  0  0  0  0
 22 23  1  0  0  0  0
  4  2  1  0  0  0  0
 11 12  1  0  0  0  0
 24 46  1  1  0  0  0
  7 31  1  6  0  0  0
 16 17  1  0  0  0  0
  2  1  2  0  0  0  0
 13 22  1  0  0  0  0
  2  3  1  0  0  0  0
 15 16  1  0  0  0  0
 13 12  1  0  0  0  0
 13 35  1  6  0  0  0
 18 40  1  1  0  0  0
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 20 42  1  6  0  0  0
 21 43  1  0  0  0  0
 22 44  1  1  0  0  0
 23 45  1  0  0  0  0
 16 37  1  0  0  0  0
 16 38  1  0  0  0  0
 15 36  1  6  0  0  0
 17 39  1  0  0  0  0
  6 29  1  0  0  0  0
  6 30  1  0  0  0  0
  5 27  1  0  0  0  0
  5 28  1  0  0  0  0
  4 26  1  1  0  0  0
 11 34  1  1  0  0  0
  9 33  1  0  0  0  0
  8 32  1  0  0  0  0
  3 25  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0028367

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC(=O)[C@]1([H])C([H])([H])C([H])([H])[C@]2([H])C([H])=C([H])O[C@@]([H])(O[C@@]3([H])O[C@@]([H])(C([H])([H])O[H])[C@]([H])(O[H])[C@@]([H])(O[H])[C@]3([H])O[H])[C@]12[H]

> <INCHI_IDENTIFIER>
InChI=1S/C15H22O9/c16-5-8-10(17)11(18)12(19)15(23-8)24-14-9-6(3-4-22-14)1-2-7(9)13(20)21/h3-4,6-12,14-19H,1-2,5H2,(H,20,21)/t6-,7-,8+,9+,10+,11-,12+,14+,15-/m1/s1

> <INCHI_KEY>
ZUKLFFYDSALIQW-UJOXGYKDSA-N

> <FORMULA>
C15H22O9

> <MOLECULAR_WEIGHT>
346.332

> <EXACT_MASS>
346.126382288

> <JCHEM_ACCEPTOR_COUNT>
9

> <JCHEM_ATOM_COUNT>
46

> <JCHEM_AVERAGE_POLARIZABILITY>
33.61171720095324

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1S,4aR,7R,7aS)-1-{[(2R,3S,4R,5R,6S)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1H,4aH,5H,6H,7H,7aH-cyclopenta[c]pyran-7-carboxylic acid

> <ALOGPS_LOGP>
-1.71

> <JCHEM_LOGP>
-1.4069365103333331

> <ALOGPS_LOGS>
-0.70

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
12.207032092608081

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.8918979850887023

> <JCHEM_PKA_STRONGEST_BASIC>
-2.981084760155974

> <JCHEM_POLAR_SURFACE_AREA>
145.91000000000003

> <JCHEM_REFRACTIVITY>
76.8049

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.84e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1S,4aR,7R,7aS)-1-{[(2R,3S,4R,5R,6S)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1H,4aH,5H,6H,7H,7aH-cyclopenta[c]pyran-7-carboxylic acid

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 46 48  0  0  0  0  0  0  0  0999 V2000
    1.1715    1.0275    4.5116 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2235    1.5569    3.9545 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9496    0.9141    3.7950 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2441    2.9186    3.3055 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.9687    3.7892    3.6785 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6474    4.1490    2.3624 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5038    4.1348    1.3521 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.9629    4.0771   -0.0665 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7639    2.9932   -0.8221 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2154    1.8192   -0.3875 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2026    1.6500    1.0402 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.6403    0.5540    1.4007 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1429   -0.7039    0.9442 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7961   -1.0250   -0.2853 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4094   -2.2882   -0.8255 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.1310   -2.4620   -2.1687 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8350   -3.7311   -2.7481 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7535   -3.4288    0.1475 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.2786   -4.7034   -0.3038 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1022   -3.1521    1.5014 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.5116   -4.1376    2.4642 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4612   -1.7628    2.0237 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.2783   -1.5418    3.2489 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3248    2.9091    1.7605 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.7170   -0.0414    3.9352 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1355    3.4269    3.6992 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6153    4.7074    4.1645 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6676    3.3114    4.3721 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4118    3.4013    2.1176 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1428    5.1240    2.4152 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1078    5.0371    1.4876 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4106    4.9658   -0.5021 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9969    2.9453   -1.8784 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2311    1.4340    1.3584 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9434   -0.6561    0.7890 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6712   -2.2918   -1.0231 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8231   -1.6730   -2.8639 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2160   -2.3795   -2.0394 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2392   -3.7277   -3.6364 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8394   -3.5135    0.2776 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4627   -4.7400   -1.2697 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9881   -3.2555    1.4273 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4311   -4.9937    1.9942 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5235   -1.7188    2.2940 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0784   -2.3452    3.7793 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3714    3.0550    1.4580 H   0  0  0  0  0  0  0  0  0  0  0  0
 22 20  1  0
 20 18  1  0
  7  6  1  0
  6  5  1  0
  5  4  1  0
  4 24  1  0
  7 24  1  0
 18 15  1  0
 15 14  1  0
 14 13  1  0
 18 19  1  0
 20 21  1  0
  7  8  1  0
 24 11  1  0
 11 10  1  0
 10  9  1  0
  9  8  2  0
 22 23  1  0
  4  2  1  0
 11 12  1  0
 24 46  1  1
  7 31  1  6
 16 17  1  0
  2  1  2  0
 13 22  1  0
  2  3  1  0
 15 16  1  0
 13 12  1  0
 13 35  1  6
 18 40  1  1
 19 41  1  0
 20 42  1  6
 21 43  1  0
 22 44  1  1
 23 45  1  0
 16 37  1  0
 16 38  1  0
 15 36  1  6
 17 39  1  0
  6 29  1  0
  6 30  1  0
  5 27  1  0
  5 28  1  0
  4 26  1  1
 11 34  1  1
  9 33  1  0
  8 32  1  0
  3 25  1  0
M  END

HEADER    PROTEIN                                 19-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   19-JUN-21         0                                  
HETATM    1  O   UNK     0       1.172   1.028   4.512  0.00  0.00           O+0
HETATM    2  C   UNK     0       0.224   1.557   3.954  0.00  0.00           C+0
HETATM    3  O   UNK     0      -0.950   0.914   3.795  0.00  0.00           O+0
HETATM    4  C   UNK     0       0.244   2.919   3.305  0.00  0.00           C+0
HETATM    5  C   UNK     0      -0.969   3.789   3.679  0.00  0.00           C+0
HETATM    6  C   UNK     0      -1.647   4.149   2.362  0.00  0.00           C+0
HETATM    7  C   UNK     0      -0.504   4.135   1.352  0.00  0.00           C+0
HETATM    8  C   UNK     0      -0.963   4.077  -0.067  0.00  0.00           C+0
HETATM    9  C   UNK     0      -0.764   2.993  -0.822  0.00  0.00           C+0
HETATM   10  O   UNK     0      -0.215   1.819  -0.388  0.00  0.00           O+0
HETATM   11  C   UNK     0      -0.203   1.650   1.040  0.00  0.00           C+0
HETATM   12  O   UNK     0       0.640   0.554   1.401  0.00  0.00           O+0
HETATM   13  C   UNK     0       0.143  -0.704   0.944  0.00  0.00           C+0
HETATM   14  O   UNK     0       0.796  -1.025  -0.285  0.00  0.00           O+0
HETATM   15  C   UNK     0       0.409  -2.288  -0.826  0.00  0.00           C+0
HETATM   16  C   UNK     0       1.131  -2.462  -2.169  0.00  0.00           C+0
HETATM   17  O   UNK     0       0.835  -3.731  -2.748  0.00  0.00           O+0
HETATM   18  C   UNK     0       0.754  -3.429   0.148  0.00  0.00           C+0
HETATM   19  O   UNK     0       0.279  -4.703  -0.304  0.00  0.00           O+0
HETATM   20  C   UNK     0       0.102  -3.152   1.501  0.00  0.00           C+0
HETATM   21  O   UNK     0       0.512  -4.138   2.464  0.00  0.00           O+0
HETATM   22  C   UNK     0       0.461  -1.763   2.024  0.00  0.00           C+0
HETATM   23  O   UNK     0      -0.278  -1.542   3.249  0.00  0.00           O+0
HETATM   24  C   UNK     0       0.325   2.909   1.761  0.00  0.00           C+0
HETATM   25  H   UNK     0      -0.717  -0.041   3.935  0.00  0.00           H+0
HETATM   26  H   UNK     0       1.135   3.427   3.699  0.00  0.00           H+0
HETATM   27  H   UNK     0      -0.615   4.707   4.165  0.00  0.00           H+0
HETATM   28  H   UNK     0      -1.668   3.311   4.372  0.00  0.00           H+0
HETATM   29  H   UNK     0      -2.412   3.401   2.118  0.00  0.00           H+0
HETATM   30  H   UNK     0      -2.143   5.124   2.415  0.00  0.00           H+0
HETATM   31  H   UNK     0       0.108   5.037   1.488  0.00  0.00           H+0
HETATM   32  H   UNK     0      -1.411   4.966  -0.502  0.00  0.00           H+0
HETATM   33  H   UNK     0      -0.997   2.945  -1.878  0.00  0.00           H+0
HETATM   34  H   UNK     0      -1.231   1.434   1.358  0.00  0.00           H+0
HETATM   35  H   UNK     0      -0.943  -0.656   0.789  0.00  0.00           H+0
HETATM   36  H   UNK     0      -0.671  -2.292  -1.023  0.00  0.00           H+0
HETATM   37  H   UNK     0       0.823  -1.673  -2.864  0.00  0.00           H+0
HETATM   38  H   UNK     0       2.216  -2.380  -2.039  0.00  0.00           H+0
HETATM   39  H   UNK     0       1.239  -3.728  -3.636  0.00  0.00           H+0
HETATM   40  H   UNK     0       1.839  -3.514   0.278  0.00  0.00           H+0
HETATM   41  H   UNK     0       0.463  -4.740  -1.270  0.00  0.00           H+0
HETATM   42  H   UNK     0      -0.988  -3.256   1.427  0.00  0.00           H+0
HETATM   43  H   UNK     0       0.431  -4.994   1.994  0.00  0.00           H+0
HETATM   44  H   UNK     0       1.524  -1.719   2.294  0.00  0.00           H+0
HETATM   45  H   UNK     0      -0.078  -2.345   3.779  0.00  0.00           H+0
HETATM   46  H   UNK     0       1.371   3.055   1.458  0.00  0.00           H+0
CONECT    1    2                                                            
CONECT    2    4    1    3                                                  
CONECT    3    2   25                                                       
CONECT    4    5   24    2   26                                             
CONECT    5    6    4   27   28                                             
CONECT    6    7    5   29   30                                             
CONECT    7    6   24    8   31                                             
CONECT    8    7    9   32                                                  
CONECT    9   10    8   33                                                  
CONECT   10   11    9                                                       
CONECT   11   24   10   12   34                                             
CONECT   12   11   13                                                       
CONECT   13   14   22   12   35                                             
CONECT   14   15   13                                                       
CONECT   15   18   14   16   36                                             
CONECT   16   17   15   37   38                                             
CONECT   17   16   39                                                       
CONECT   18   20   15   19   40                                             
CONECT   19   18   41                                                       
CONECT   20   22   18   21   42                                             
CONECT   21   20   43                                                       
CONECT   22   20   23   13   44                                             
CONECT   23   22   45                                                       
CONECT   24    4    7   11   46                                             
CONECT   25    3                                                            
CONECT   26    4                                                            
CONECT   27    5                                                            
CONECT   28    5                                                            
CONECT   29    6                                                            
CONECT   30    6                                                            
CONECT   31    7                                                            
CONECT   32    8                                                            
CONECT   33    9                                                            
CONECT   34   11                                                            
CONECT   35   13                                                            
CONECT   36   15                                                            
CONECT   37   16                                                            
CONECT   38   16                                                            
CONECT   39   17                                                            
CONECT   40   18                                                            
CONECT   41   19                                                            
CONECT   42   20                                                            
CONECT   43   21                                                            
CONECT   44   22                                                            
CONECT   45   23                                                            
CONECT   46   24                                                            
MASTER        0    0    0    0    0    0    0    0   46    0   96    0
END

RDKit          3D

46 48  0  0  0  0  0  0  0  0999 V2000
    1.1715    1.0275    4.5116 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2235    1.5569    3.9545 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9496    0.9141    3.7950 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2441    2.9186    3.3055 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.9687    3.7892    3.6785 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6474    4.1490    2.3624 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5038    4.1348    1.3521 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.9629    4.0771   -0.0665 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7639    2.9932   -0.8221 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2154    1.8192   -0.3875 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2026    1.6500    1.0402 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.6403    0.5540    1.4007 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1429   -0.7039    0.9442 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7961   -1.0250   -0.2853 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4094   -2.2882   -0.8255 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.1310   -2.4620   -2.1687 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8350   -3.7311   -2.7481 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7535   -3.4288    0.1475 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.2786   -4.7034   -0.3038 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1022   -3.1521    1.5014 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.5116   -4.1376    2.4642 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4612   -1.7628    2.0237 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.2783   -1.5418    3.2489 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3248    2.9091    1.7605 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.7170   -0.0414    3.9352 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1355    3.4269    3.6992 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6153    4.7074    4.1645 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6676    3.3114    4.3721 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4118    3.4013    2.1176 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1428    5.1240    2.4152 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1078    5.0371    1.4876 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4106    4.9658   -0.5021 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9969    2.9453   -1.8784 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2311    1.4340    1.3584 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9434   -0.6561    0.7890 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6712   -2.2918   -1.0231 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8231   -1.6730   -2.8639 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2160   -2.3795   -2.0394 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2392   -3.7277   -3.6364 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8394   -3.5135    0.2776 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4627   -4.7400   -1.2697 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9881   -3.2555    1.4273 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4311   -4.9937    1.9942 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5235   -1.7188    2.2940 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0784   -2.3452    3.7793 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3714    3.0550    1.4580 H   0  0  0  0  0  0  0  0  0  0  0  0
 22 20  1  0
 20 18  1  0
  7  6  1  0
  6  5  1  0
  5  4  1  0
  4 24  1  0
  7 24  1  0
 18 15  1  0
 15 14  1  0
 14 13  1  0
 18 19  1  0
 20 21  1  0
  7  8  1  0
 24 11  1  0
 11 10  1  0
 10  9  1  0
  9  8  2  0
 22 23  1  0
  4  2  1  0
 11 12  1  0
 24 46  1  1
  7 31  1  6
 16 17  1  0
  2  1  2  0
 13 22  1  0
  2  3  1  0
 15 16  1  0
 13 12  1  0
 13 35  1  6
 18 40  1  1
 19 41  1  0
 20 42  1  6
 21 43  1  0
 22 44  1  1
 23 45  1  0
 16 37  1  0
 16 38  1  0
 15 36  1  6
 17 39  1  0
  6 29  1  0
  6 30  1  0
  5 27  1  0
  5 28  1  0
  4 26  1  1
 11 34  1  1
  9 33  1  0
  8 32  1  0
  3 25  1  0
M  END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₅H₂₂O₉

Average Mass

346.3320 Da

Monoisotopic Mass

346.12638 Da

IUPAC Name

(1S,4aR,7R,7aS)-1-{[(2R,3S,4R,5R,6S)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1H,4aH,5H,6H,7H,7aH-cyclopenta[c]pyran-7-carboxylic acid

Traditional Name

(1S,4aR,7R,7aS)-1-{[(2R,3S,4R,5R,6S)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1H,4aH,5H,6H,7H,7aH-cyclopenta[c]pyran-7-carboxylic acid

CAS Registry Number

Not Available

SMILES

[H]OC(=O)[C@]1([H])C([H])([H])C([H])([H])[C@]2([H])C([H])=C([H])O[C@@]([H])(O[C@@]3([H])O[C@@]([H])(C([H])([H])O[H])[C@]([H])(O[H])[C@@]([H])(O[H])[C@]3([H])O[H])[C@]12[H]

InChI Identifier

InChI=1S/C15H22O9/c16-5-8-10(17)11(18)12(19)15(23-8)24-14-9-6(3-4-22-14)1-2-7(9)13(20)21/h3-4,6-12,14-19H,1-2,5H2,(H,20,21)/t6-,7-,8+,9+,10+,11-,12+,14+,15-/m1/s1

InChI Key

ZUKLFFYDSALIQW-UJOXGYKDSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Thunbergia laurifolia	JEOL database	Kanchanapoom, T., et al, Phytochemistry 60, 769 (2002)

Chemical Taxonomy

Classification

Not classified

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	-1.7	ALOGPS
logP	-1.4	ChemAxon
logS	-0.7	ALOGPS
pKa (Strongest Acidic)	3.89	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	9	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	145.91 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	76.8 m³·mol⁻¹	ChemAxon
Polarizability	33.61 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

Not Available

References

General References

Kanchanapoom, T., et al. (2002). Kanchanapoom, T., et al, Phytochemistry 60, 769 (2002). Phytochem..

Showing NP-Card for 8-epi-grandifloric acid (NP0028367)

MOL for NP0028367 (8-epi-grandifloric acid)

3D MOL for NP0028367 (8-epi-grandifloric acid)

3D SDF for NP0028367 (8-epi-grandifloric acid)

3D-SDF for NP0028367 (8-epi-grandifloric acid)

PDB for NP0028367 (8-epi-grandifloric acid)

3D PDB for NP0028367 (8-epi-grandifloric acid)

SMILES for NP0028367 (8-epi-grandifloric acid)

INCHI for NP0028367 (8-epi-grandifloric acid)

Structure for NP0028367 (8-epi-grandifloric acid)

3D Structure for NP0028367 (8-epi-grandifloric acid)