NP-MRD: Showing NP-Card for Yunnaneic acid B (NP0075908)

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Record Information

Version

2.0

Created at

2022-04-28 21:07:07 UTC

Updated at

2022-04-28 21:07:07 UTC

NP-MRD ID

NP0075908

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Yunnaneic acid B

Description

(1R,1'R,2S,2'R,4R,6'S,7S,7'R,8S,10'S,11'S)-5,9'-bis[(1E)-3-[(1S)-1-carboxy-2-(3,4-dihydroxyphenyl)ethoxy]-3-oxoprop-1-en-1-yl]-7,11'-bis(3,4-dihydroxyphenyl)-2',6'-dihydroxy-3-oxo-3',5'-dioxaspiro[bicyclo[2.2.2]Octane-2,4'-tricyclo[5.2.2.0²,⁶]Undecane]-5,8'-diene-8,10'-dicarboxylic acid belongs to the class of organic compounds known as hexacarboxylic acids and derivatives. These are carboxylic acids containing exactly six carboxyl groups. Yunnaneic acid B is found in Salvia yunnanensis. Based on a literature review very few articles have been published on (1R,1'R,2S,2'R,4R,6'S,7S,7'R,8S,10'S,11'S)-5,9'-bis[(1E)-3-[(1S)-1-carboxy-2-(3,4-dihydroxyphenyl)ethoxy]-3-oxoprop-1-en-1-yl]-7,11'-bis(3,4-dihydroxyphenyl)-2',6'-dihydroxy-3-oxo-3',5'-dioxaspiro[bicyclo[2.2.2]Octane-2,4'-tricyclo[5.2.2.0²,⁶]Undecane]-5,8'-diene-8,10'-dicarboxylic acid.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304282223072D          

 79 87  0  0  1  0            999 V2000
    4.2736    0.1042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5285   -0.2499    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8492    0.2183    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.0042    0.9655    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.7494    1.3196    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.3394    0.9266    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.7837    0.8147    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5232    1.5975    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2869    0.5786    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.7471    1.2025    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0622    0.9711    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.0569    0.0599    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.8603   -0.1276    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3800   -0.4117    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.6331   -0.0613    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.5632    0.7607    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.1509    1.3075    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.1497    0.6727    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1964    0.1246    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9741    0.6417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3595   -0.0878    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1839   -0.1188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6230    0.5797    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5693   -0.8482    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3937   -0.8792    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.2187   -0.8840    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6271   -1.6009    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4520   -1.6056    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8604   -2.3225    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4438   -3.0345    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6188   -3.0298    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2104   -2.3129    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2022   -3.7418    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.8521   -3.7514    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7436   -0.1055    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2625    0.5647    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4141   -0.2025    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1837    1.1111    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8606    0.6395    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2537    1.9332    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0438   -0.5329    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7907   -0.1825    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4676   -0.6541    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3976   -1.4762    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6507   -1.8266    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0262   -1.3550    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5807   -2.6486    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0745   -1.9478    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2124   -0.7503    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0033    1.7068    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7260    2.2172    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4711    2.5713    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0467    2.6854    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2358    1.5089    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4907    1.1547    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8114    1.6229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8772    2.4453    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6224    2.7995    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3016    2.3312    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6882    3.6218    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1980    2.9135    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9528   -0.3640    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6980   -0.0098    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3772   -0.4780    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3114   -1.3004    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1223   -0.1239    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.8016   -0.5921    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    7.7358   -1.4145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4150   -1.8827    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.9906   -1.7686    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.5467   -0.2379    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2260   -0.7062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9711   -0.3520    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6504   -0.8202    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5845   -1.6426    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8394   -1.9967    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1601   -1.5285    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7735   -2.8191    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.2638   -2.1108    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  3  2  1  6  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  1  1  6  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  7  9  1  0  0  0  0
  3  9  1  0  0  0  0
  9 10  1  1  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
  9 13  1  0  0  0  0
 12 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 11 17  1  0  0  0  0
 17 18  1  6  0  0  0
 18 19  2  0  0  0  0
 14 19  1  6  0  0  0
 18 20  1  0  0  0  0
 20 21  2  0  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 22 24  1  0  0  0  0
 25 24  1  6  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  2  0  0  0  0
 28 29  1  0  0  0  0
 29 30  2  0  0  0  0
 30 31  1  0  0  0  0
 31 32  2  0  0  0  0
 27 32  1  0  0  0  0
 31 33  1  0  0  0  0
 30 34  1  0  0  0  0
 25 35  1  0  0  0  0
 35 36  2  0  0  0  0
 35 37  1  0  0  0  0
 16 38  1  6  0  0  0
 38 39  2  0  0  0  0
 38 40  1  0  0  0  0
 15 41  1  6  0  0  0
 41 42  2  0  0  0  0
 42 43  1  0  0  0  0
 43 44  2  0  0  0  0
 44 45  1  0  0  0  0
 45 46  2  0  0  0  0
 41 46  1  0  0  0  0
 45 47  1  0  0  0  0
 44 48  1  0  0  0  0
 12 49  1  6  0  0  0
 11 50  1  6  0  0  0
  5 51  1  6  0  0  0
 51 52  2  0  0  0  0
 51 53  1  0  0  0  0
  4 54  1  6  0  0  0
 54 55  2  0  0  0  0
 55 56  1  0  0  0  0
 56 57  2  0  0  0  0
 57 58  1  0  0  0  0
 58 59  2  0  0  0  0
 54 59  1  0  0  0  0
 58 60  1  0  0  0  0
 57 61  1  0  0  0  0
  1 62  1  0  0  0  0
 62 63  2  0  0  0  0
 63 64  1  0  0  0  0
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 64 66  1  0  0  0  0
 67 66  1  1  0  0  0
 67 68  1  0  0  0  0
 68 69  2  0  0  0  0
 68 70  1  0  0  0  0
 67 71  1  0  0  0  0
 71 72  1  0  0  0  0
 72 73  2  0  0  0  0
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 76 77  2  0  0  0  0
 72 77  1  0  0  0  0
 76 78  1  0  0  0  0
 75 79  1  0  0  0  0
M  END

     RDKit          3D

125133  0  0  0  0  0  0  0  0999 V2000
    4.5397    1.4444   -2.6606 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3468    1.3817   -1.4214 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2628    2.1317   -0.7823 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4286    2.8882   -1.4656 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3506    3.6427   -0.8956 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4752    4.4050   -1.5313 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9026    4.3580   -0.8593 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.8211    5.2166    0.3962 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.2498    6.5776    0.1683 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6142    7.4036   -0.7224 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0183    8.7108   -0.9496 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0851    9.2093   -0.2709 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4929   10.5240   -0.4979 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7482    8.4212    0.6261 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8352    8.9458    1.3099 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3261    7.1081    0.8411 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5395    5.0092    1.0024 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.5249    6.0405    0.7495 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5667    5.7864    0.1031 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3394    7.3285    1.2148 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0817    3.6199    0.5782 C   0  0  1  0  0  0  0  0  0  0  0  0
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   -4.3662   -7.4690    1.2073 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5752   -7.9209    0.1799 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2867   -7.4044   -0.0418 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5494   -7.9034   -1.0909 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.5423   -5.9113    0.5767 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6094   -5.9662    1.8313 C   0  0  0  0  0  0  0  0  0  0  0  0
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M  END


  Mrv1652304282223072D          

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 72 77  1  0  0  0  0
 76 78  1  0  0  0  0
 75 79  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0075908

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC(=O)[C@H](CC1=CC=C(O)C(O)=C1)OC(=O)\C=C\C1=C[C@@H]2[C@@H]([C@@H]([C@H]1C(=O)[C@]21O[C@@]2(O)[C@@H]3C=C(\C=C\C(=O)O[C@@H](CC4=CC=C(O)C(O)=C4)C(O)=O)[C@@H]([C@H]([C@H]3C3=CC=C(O)C(O)=C3)C(O)=O)[C@@]2(O)O1)C(O)=O)C1=CC=C(O)C(O)=C1

> <INCHI_IDENTIFIER>
InChI=1S/C54H46O25/c55-29-7-1-21(13-33(29)59)15-37(48(66)67)76-39(63)11-5-23-17-27-41(24-3-9-31(57)35(61)19-24)44(50(70)71)43(23)47(65)52(27)78-53(74)28-18-26(6-12-40(64)77-38(49(68)69)16-22-2-8-30(56)34(60)14-22)46(54(53,75)79-52)45(51(72)73)42(28)25-4-10-32(58)36(62)20-25/h1-14,17-20,27-28,37-38,41-46,55-62,74-75H,15-16H2,(H,66,67)(H,68,69)(H,70,71)(H,72,73)/b11-5+,12-6+/t27-,28-,37+,38+,41+,42+,43+,44+,45+,46+,52+,53+,54-/m1/s1

> <INCHI_KEY>
UYOUXKDGHGVDEM-UBLZNYDLSA-N

> <FORMULA>
C54H46O25

> <MOLECULAR_WEIGHT>
1094.937

> <EXACT_MASS>
1094.232816981

> <JCHEM_ACCEPTOR_COUNT>
23

> <JCHEM_ATOM_COUNT>
125

> <JCHEM_AVERAGE_POLARIZABILITY>
104.5696917902284

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
14

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1R,1'R,2S,2'R,4R,6'S,7S,7'R,8S,10'S,11'S)-5,9'-bis[(1E)-3-[(1S)-1-carboxy-2-(3,4-dihydroxyphenyl)ethoxy]-3-oxoprop-1-en-1-yl]-7,11'-bis(3,4-dihydroxyphenyl)-2',6'-dihydroxy-3-oxo-3',5'-dioxaspiro[bicyclo[2.2.2]octane-2,4'-tricyclo[5.2.2.0^{2,6}]undecane]-5,8'-diene-8,10'-dicarboxylic acid

> <ALOGPS_LOGP>
3.64

> <JCHEM_LOGP>
5.016395736333335

> <ALOGPS_LOGS>
-4.02

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
9

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-4

> <JCHEM_PKA>
3.2786376027207886

> <JCHEM_PKA_STRONGEST_ACIDIC>
2.8249117029867152

> <JCHEM_PKA_STRONGEST_BASIC>
-6.295784376378564

> <JCHEM_POLAR_SURFACE_AREA>
439.63000000000005

> <JCHEM_REFRACTIVITY>
264.64990000000006

> <JCHEM_ROTATABLE_BOND_COUNT>
18

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.04e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1R,1'R,2S,2'R,4R,6'S,7S,7'R,8S,10'S,11'S)-5,9'-bis[(1E)-3-[(1S)-1-carboxy-2-(3,4-dihydroxyphenyl)ethoxy]-3-oxoprop-1-en-1-yl]-7,11'-bis(3,4-dihydroxyphenyl)-2',6'-dihydroxy-3-oxo-3',5'-dioxaspiro[bicyclo[2.2.2]octane-2,4'-tricyclo[5.2.2.0^{2,6}]undecane]-5,8'-diene-8,10'-dicarboxylic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 28-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   28-APR-22         0                                  
HETATM    1  C   UNK     0       7.977   0.195   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       6.586  -0.467   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       5.318   0.407   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       5.608   1.802   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       6.999   2.463   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       8.100   1.730   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       7.063   1.521   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       6.577   2.982   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       6.136   1.080   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       5.128   2.245   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       3.849   1.813   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       3.840   0.112   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       5.339  -0.238   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       2.576  -0.769   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       1.182  -0.114   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       1.051   1.420   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       2.148   2.441   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       2.146   1.256   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       2.233   0.233   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       3.685   1.198   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       4.404  -0.164   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       5.943  -0.222   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       6.763   1.082   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0       6.663  -1.583   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       8.202  -1.641   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       9.742  -1.650   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      10.504  -2.988   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      12.044  -2.997   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      12.806  -4.335   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      12.028  -5.664   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      10.488  -5.656   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       9.726  -4.317   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0       9.711  -6.985   0.000  0.00  0.00           O+0
HETATM   34  O   UNK     0      12.791  -7.003   0.000  0.00  0.00           O+0
HETATM   35  C   UNK     0       8.855  -0.197   0.000  0.00  0.00           C+0
HETATM   36  O   UNK     0       7.957   1.054   0.000  0.00  0.00           O+0
HETATM   37  O   UNK     0      10.106  -0.378   0.000  0.00  0.00           O+0
HETATM   38  C   UNK     0      -0.343   2.074   0.000  0.00  0.00           C+0
HETATM   39  O   UNK     0      -1.607   1.194   0.000  0.00  0.00           O+0
HETATM   40  O   UNK     0      -0.474   3.609   0.000  0.00  0.00           O+0
HETATM   41  C   UNK     0      -0.082  -0.995   0.000  0.00  0.00           C+0
HETATM   42  C   UNK     0      -1.476  -0.341   0.000  0.00  0.00           C+0
HETATM   43  C   UNK     0      -2.739  -1.221   0.000  0.00  0.00           C+0
HETATM   44  C   UNK     0      -2.609  -2.755   0.000  0.00  0.00           C+0
HETATM   45  C   UNK     0      -1.215  -3.410   0.000  0.00  0.00           C+0
HETATM   46  C   UNK     0       0.049  -2.529   0.000  0.00  0.00           C+0
HETATM   47  O   UNK     0      -1.084  -4.944   0.000  0.00  0.00           O+0
HETATM   48  O   UNK     0      -3.872  -3.636   0.000  0.00  0.00           O+0
HETATM   49  O   UNK     0       4.130  -1.401   0.000  0.00  0.00           O+0
HETATM   50  O   UNK     0       3.739   3.186   0.000  0.00  0.00           O+0
HETATM   51  C   UNK     0       6.955   4.139   0.000  0.00  0.00           C+0
HETATM   52  O   UNK     0       8.346   4.800   0.000  0.00  0.00           O+0
HETATM   53  O   UNK     0       5.687   5.013   0.000  0.00  0.00           O+0
HETATM   54  C   UNK     0       4.173   2.817   0.000  0.00  0.00           C+0
HETATM   55  C   UNK     0       2.783   2.155   0.000  0.00  0.00           C+0
HETATM   56  C   UNK     0       1.515   3.029   0.000  0.00  0.00           C+0
HETATM   57  C   UNK     0       1.638   4.565   0.000  0.00  0.00           C+0
HETATM   58  C   UNK     0       3.028   5.226   0.000  0.00  0.00           C+0
HETATM   59  C   UNK     0       4.296   4.352   0.000  0.00  0.00           C+0
HETATM   60  O   UNK     0       3.151   6.761   0.000  0.00  0.00           O+0
HETATM   61  O   UNK     0       0.370   5.439   0.000  0.00  0.00           O+0
HETATM   62  C   UNK     0       9.245  -0.679   0.000  0.00  0.00           C+0
HETATM   63  C   UNK     0      10.636  -0.018   0.000  0.00  0.00           C+0
HETATM   64  C   UNK     0      11.904  -0.892   0.000  0.00  0.00           C+0
HETATM   65  O   UNK     0      11.781  -2.427   0.000  0.00  0.00           O+0
HETATM   66  O   UNK     0      13.295  -0.231   0.000  0.00  0.00           O+0
HETATM   67  C   UNK     0      14.563  -1.105   0.000  0.00  0.00           C+0
HETATM   68  C   UNK     0      14.440  -2.640   0.000  0.00  0.00           C+0
HETATM   69  O   UNK     0      15.708  -3.514   0.000  0.00  0.00           O+0
HETATM   70  O   UNK     0      13.049  -3.301   0.000  0.00  0.00           O+0
HETATM   71  C   UNK     0      15.954  -0.444   0.000  0.00  0.00           C+0
HETATM   72  C   UNK     0      17.222  -1.318   0.000  0.00  0.00           C+0
HETATM   73  C   UNK     0      18.613  -0.657   0.000  0.00  0.00           C+0
HETATM   74  C   UNK     0      19.881  -1.531   0.000  0.00  0.00           C+0
HETATM   75  C   UNK     0      19.758  -3.066   0.000  0.00  0.00           C+0
HETATM   76  C   UNK     0      18.367  -3.727   0.000  0.00  0.00           C+0
HETATM   77  C   UNK     0      17.099  -2.853   0.000  0.00  0.00           C+0
HETATM   78  O   UNK     0      18.244  -5.262   0.000  0.00  0.00           O+0
HETATM   79  O   UNK     0      21.026  -3.940   0.000  0.00  0.00           O+0
CONECT    1    2    6   62                                                  
CONECT    2    1    3                                                       
CONECT    3    2    4    9                                                  
CONECT    4    3    5   54                                                  
CONECT    5    4    6   51                                                  
CONECT    6    5    1    7                                                  
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7    3   10   13                                             
CONECT   10    9   11                                                       
CONECT   11   10   12   17   50                                             
CONECT   12   11   13   14   49                                             
CONECT   13   12    9                                                       
CONECT   14   12   15   19                                                  
CONECT   15   14   16   41                                                  
CONECT   16   15   17   38                                                  
CONECT   17   16   11   18                                                  
CONECT   18   17   19   20                                                  
CONECT   19   18   14                                                       
CONECT   20   18   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22   25                                                       
CONECT   25   24   26   35                                                  
CONECT   26   25   27                                                       
CONECT   27   26   28   32                                                  
CONECT   28   27   29                                                       
CONECT   29   28   30                                                       
CONECT   30   29   31   34                                                  
CONECT   31   30   32   33                                                  
CONECT   32   31   27                                                       
CONECT   33   31                                                            
CONECT   34   30                                                            
CONECT   35   25   36   37                                                  
CONECT   36   35                                                            
CONECT   37   35                                                            
CONECT   38   16   39   40                                                  
CONECT   39   38                                                            
CONECT   40   38                                                            
CONECT   41   15   42   46                                                  
CONECT   42   41   43                                                       
CONECT   43   42   44                                                       
CONECT   44   43   45   48                                                  
CONECT   45   44   46   47                                                  
CONECT   46   45   41                                                       
CONECT   47   45                                                            
CONECT   48   44                                                            
CONECT   49   12                                                            
CONECT   50   11                                                            
CONECT   51    5   52   53                                                  
CONECT   52   51                                                            
CONECT   53   51                                                            
CONECT   54    4   55   59                                                  
CONECT   55   54   56                                                       
CONECT   56   55   57                                                       
CONECT   57   56   58   61                                                  
CONECT   58   57   59   60                                                  
CONECT   59   58   54                                                       
CONECT   60   58                                                            
CONECT   61   57                                                            
CONECT   62    1   63                                                       
CONECT   63   62   64                                                       
CONECT   64   63   65   66                                                  
CONECT   65   64                                                            
CONECT   66   64   67                                                       
CONECT   67   66   68   71                                                  
CONECT   68   67   69   70                                                  
CONECT   69   68                                                            
CONECT   70   68                                                            
CONECT   71   67   72                                                       
CONECT   72   71   73   77                                                  
CONECT   73   72   74                                                       
CONECT   74   73   75                                                       
CONECT   75   74   76   79                                                  
CONECT   76   75   77   78                                                  
CONECT   77   76   72                                                       
CONECT   78   76                                                            
CONECT   79   75                                                            
MASTER        0    0    0    0    0    0    0    0   79    0  174    0
END

View in JSmol

Synonyms

Value	Source
(1R,1'r,2S,2'r,4R,6's,7S,7'r,8S,10's,11's)-5,9'-Bis[(1E)-3-[(1S)-1-carboxy-2-(3,4-dihydroxyphenyl)ethoxy]-3-oxoprop-1-en-1-yl]-7,11'-bis(3,4-dihydroxyphenyl)-2',6'-dihydroxy-3-oxo-3',5'-dioxaspiro[bicyclo[2.2.2]octane-2,4'-tricyclo[5.2.2.0,]undecane]-5,8'-diene-8,10'-dicarboxylate	Generator

Chemical Formula

C₅₄H₄₆O₂₅

Average Mass

1094.9370 Da

Monoisotopic Mass

1094.23282 Da

IUPAC Name

Traditional Name

CAS Registry Number

Not Available

SMILES

OC(=O)[C@H](CC1=CC=C(O)C(O)=C1)OC(=O)\C=C\C1=C[C@@H]2[C@@H]([C@@H]([C@H]1C(=O)[C@]21O[C@@]2(O)[C@@H]3C=C(\C=C\C(=O)O[C@@H](CC4=CC=C(O)C(O)=C4)C(O)=O)[C@@H]([C@H]([C@H]3C3=CC=C(O)C(O)=C3)C(O)=O)[C@@]2(O)O1)C(O)=O)C1=CC=C(O)C(O)=C1

InChI Identifier

InChI=1S/C54H46O25/c55-29-7-1-21(13-33(29)59)15-37(48(66)67)76-39(63)11-5-23-17-27-41(24-3-9-31(57)35(61)19-24)44(50(70)71)43(23)47(65)52(27)78-53(74)28-18-26(6-12-40(64)77-38(49(68)69)16-22-2-8-30(56)34(60)14-22)46(54(53,75)79-52)45(51(72)73)42(28)25-4-10-32(58)36(62)20-25/h1-14,17-20,27-28,37-38,41-46,55-62,74-75H,15-16H2,(H,66,67)(H,68,69)(H,70,71)(H,72,73)/b11-5+,12-6+/t27-,28-,37+,38+,41+,42+,43+,44+,45+,46+,52+,53+,54-/m1/s1

InChI Key

UYOUXKDGHGVDEM-UBLZNYDLSA-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
Salvia Yunnanensis	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as hexacarboxylic acids and derivatives. These are carboxylic acids containing exactly six carboxyl groups.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Hexacarboxylic acids and derivatives

Direct Parent

Hexacarboxylic acids and derivatives

Alternative Parents

Substituents

Hexacarboxylic acid or derivatives
Cyclohexylphenol
3-phenylpropanoic-acid
Catechol
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Ketal
Cyclohexenone
Phenol
Fatty acid ester
Fatty acyl
Benzenoid
Monocyclic benzene moiety
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Cyclic alcohol
Meta-dioxolane
Ketone
Hemiacetal
Carboxylic acid ester
Oxacycle
Organoheterocyclic compound
Carboxylic acid
Acetal
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
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	3.64	ALOGPS
logP	5.02	ChemAxon
logS	-4	ALOGPS
pKa (Strongest Acidic)	2.82	ChemAxon
pKa (Strongest Basic)	-6.3	ChemAxon
Physiological Charge	-4	ChemAxon
Hydrogen Acceptor Count	23	ChemAxon
Hydrogen Donor Count	14	ChemAxon
Polar Surface Area	439.63 Å²	ChemAxon
Rotatable Bond Count	18	ChemAxon
Refractivity	264.65 m³·mol⁻¹	ChemAxon
Polarizability	104.57 Å³	ChemAxon
Number of Rings	9	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

163068276

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Showing NP-Card for Yunnaneic acid B (NP0075908)

MOL for NP0075908 (Yunnaneic acid B)

3D MOL for NP0075908 (Yunnaneic acid B)

3D SDF for NP0075908 (Yunnaneic acid B)

3D-SDF for NP0075908 (Yunnaneic acid B)

PDB for NP0075908 (Yunnaneic acid B)

3D PDB for NP0075908 (Yunnaneic acid B)

SMILES for NP0075908 (Yunnaneic acid B)

INCHI for NP0075908 (Yunnaneic acid B)

Structure for NP0075908 (Yunnaneic acid B)

3D Structure for NP0075908 (Yunnaneic acid B)