NP-MRD: Showing NP-Card for (2s,3's,4ar,5r,6r,8ar)-5-[(1r)-1-(acetyloxy)-2-carboxyethyl]-2-[furan-3-yl({[(2r,3r,4s,5s,6s)-3,4,5-trihydroxy-6-methoxyoxan-2-yl]oxy})methyl]-6-(2-hydroxypropan-2-yl)-2,5,8a-trimethyl-8-oxo-tetrahydro-3h-spiro[naphthalene-1,2'-oxirane]-3'-carboxylic acid (NP0215786)

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Record Information

Version

2.0

Created at

2022-09-05 15:30:55 UTC

Updated at

2022-09-05 15:30:55 UTC

NP-MRD ID

NP0215786

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(2s,3's,4ar,5r,6r,8ar)-5-[(1r)-1-(acetyloxy)-2-carboxyethyl]-2-[furan-3-yl({[(2r,3r,4s,5s,6s)-3,4,5-trihydroxy-6-methoxyoxan-2-yl]oxy})methyl]-6-(2-hydroxypropan-2-yl)-2,5,8a-trimethyl-8-oxo-tetrahydro-3h-spiro[naphthalene-1,2'-oxirane]-3'-carboxylic acid

Description

Nomilinic acid 17-beta-D-glucopyranoside belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units. (2s,3's,4ar,5r,6r,8ar)-5-[(1r)-1-(acetyloxy)-2-carboxyethyl]-2-[furan-3-yl({[(2r,3r,4s,5s,6s)-3,4,5-trihydroxy-6-methoxyoxan-2-yl]oxy})methyl]-6-(2-hydroxypropan-2-yl)-2,5,8a-trimethyl-8-oxo-tetrahydro-3h-spiro[naphthalene-1,2'-oxirane]-3'-carboxylic acid is found in Citrus hystrix and Citrus maxima. (2s,3's,4ar,5r,6r,8ar)-5-[(1r)-1-(acetyloxy)-2-carboxyethyl]-2-[furan-3-yl({[(2r,3r,4s,5s,6s)-3,4,5-trihydroxy-6-methoxyoxan-2-yl]oxy})methyl]-6-(2-hydroxypropan-2-yl)-2,5,8a-trimethyl-8-oxo-tetrahydro-3h-spiro[naphthalene-1,2'-oxirane]-3'-carboxylic acid was first documented in 2003 (PMID: 14710824). Based on a literature review a small amount of articles have been published on Nomilinic acid 17-beta-D-glucopyranoside (PMID: 15997847).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309052217302D          

 50 54  0  0  1  0            999 V2000
    0.4183    4.9919    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9225    4.3389    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6092    3.5757    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.1134    2.9228    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8000    2.1596    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.3043    1.5066    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1219    1.6168    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4352    2.3800    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0020    3.0821    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5359    3.7111    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2991    3.3977    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2369    2.5751    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6261    0.9639    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.8955    0.5807    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1816    1.5738    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9876    1.3978    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2381    0.6117    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.0441    0.4356    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.8617    0.5458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0775    1.2599    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.3804    1.7011    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4138    2.5254    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7167    2.9665    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1444    2.9086    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8081    1.6431    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8416    2.4675    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5369    3.2341    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5722    2.8507    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2946   -0.3504    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.1006   -0.5265    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9066   -0.7026    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9245   -1.3325    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2767    0.2795    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7391   -0.9604    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9331   -0.7843    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3776   -1.3943    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6826    0.0017    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.1271   -0.6082    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8766    0.1778    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7005   -0.6282    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0906   -0.0727    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.2846    0.1034    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0341    0.8894    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7291   -0.5066    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0176    2.0494    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.3309    1.2862    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5218    2.7024    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.3394    2.5922    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2084    3.4655    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.7127    4.1185    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  3  2  1  1  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  1  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
  8 12  2  0  0  0  0
 13  7  1  6  0  0  0
 13 14  1  1  0  0  0
 13 15  1  0  0  0  0
 15 16  1  0  0  0  0
 17 16  1  6  0  0  0
 17 18  1  0  0  0  0
 18 19  1  6  0  0  0
 18 20  1  1  0  0  0
 20 21  1  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
 20 25  1  1  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 26 28  2  0  0  0  0
 18 29  1  0  0  0  0
 29 30  1  6  0  0  0
 30 31  1  0  0  0  0
 30 32  1  0  0  0  0
 30 33  1  0  0  0  0
 29 34  1  0  0  0  0
 34 35  1  0  0  0  0
 35 36  2  0  0  0  0
 35 37  1  0  0  0  0
 17 37  1  0  0  0  0
 37 38  1  6  0  0  0
 37 39  1  0  0  0  0
 13 39  1  0  0  0  0
 39 40  1  0  0  0  0
 40 41  1  0  0  0  0
 39 41  1  0  0  0  0
 41 42  1  6  0  0  0
 42 43  2  0  0  0  0
 42 44  1  0  0  0  0
  5 45  1  0  0  0  0
 45 46  1  6  0  0  0
 45 47  1  0  0  0  0
 47 48  1  1  0  0  0
 47 49  1  0  0  0  0
  3 49  1  0  0  0  0
 49 50  1  6  0  0  0
M  END

     RDKit          3D

 98102  0  0  0  0  0  0  0  0999 V2000
   -7.1349    2.2976    0.5019 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2392    0.9293    0.7475 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2909    0.2003    0.0450 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.4374   -0.4116    0.9595 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.3154    0.2858    1.1350 C   0  0  1  0  0  0  0  0  0  0  0  0
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   -3.1842    1.4791    4.4764 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9194    0.5211    3.6599 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8406    0.0096    1.0894 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.5908   -0.8376    2.3565 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1526    1.3037    1.2647 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3129    1.3713    0.9134 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7669    0.3169    0.0170 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.1248    0.3189   -0.6315 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.1315    0.9497   -2.0036 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2115    1.0362    0.1390 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.5240    1.0747   -0.5562 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5795    1.7138    0.2634 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5062    2.1643    1.4072 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.8835    1.8487   -0.3122 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9900    2.3414    0.5049 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8908    2.9711    1.6841 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6557    4.4185    1.7756 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0048    2.2871    2.7017 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3838   -1.1366   -0.8408 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.5231   -1.9661   -1.0086 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5749   -2.1280    0.0448 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.1037    1.2170   -1.4685 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -4.4488   -1.6782   -0.7537 C   0  0  2  0  0  0  0  0  0  0  0  0
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  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
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  8 12  2  0
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 25 26  1  0
 26 27  1  0
 26 28  2  0
 18 29  1  0
 29 34  1  0
 34 35  1  0
 35 36  2  0
 35 37  1  0
 37 38  1  6
 37 39  1  0
 39 40  1  1
 40 41  1  0
 41 42  1  0
 42 44  1  0
 42 43  2  0
 29 30  1  0
 30 31  1  0
 30 32  1  0
 30 33  1  0
  5 45  1  0
 45 46  1  0
 45 47  1  0
 47 48  1  0
 47 49  1  0
 49 50  1  0
 49  3  1  0
  9  8  1  0
 39 13  1  0
 41 39  1  0
 37 17  1  0
  1 51  1  0
  1 52  1  0
  1 53  1  0
  3 54  1  6
  5 55  1  6
  7 56  1  6
 12 59  1  0
 10 58  1  0
  9 57  1  0
 14 60  1  0
 14 61  1  0
 14 62  1  0
 15 63  1  0
 15 64  1  0
 16 65  1  0
 16 66  1  0
 17 67  1  1
 19 68  1  0
 19 69  1  0
 19 70  1  0
 20 71  1  1
 21 72  1  0
 21 73  1  0
 24 74  1  0
 27 75  1  0
 27 76  1  0
 27 77  1  0
 29 78  1  1
 34 86  1  0
 34 87  1  0
 38 88  1  0
 38 89  1  0
 38 90  1  0
 41 91  1  1
 44 92  1  0
 31 79  1  0
 31 80  1  0
 31 81  1  0
 32 82  1  0
 32 83  1  0
 32 84  1  0
 33 85  1  0
 45 93  1  1
 46 94  1  0
 47 95  1  6
 48 96  1  0
 49 97  1  1
 50 98  1  0
M  END


  Mrv1652309052217302D          

 50 54  0  0  1  0            999 V2000
    0.4183    4.9919    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9225    4.3389    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6092    3.5757    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.1134    2.9228    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8000    2.1596    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.3043    1.5066    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1219    1.6168    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4352    2.3800    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0020    3.0821    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5359    3.7111    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2991    3.3977    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2369    2.5751    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6261    0.9639    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.8955    0.5807    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1816    1.5738    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9876    1.3978    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2381    0.6117    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.0441    0.4356    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.8617    0.5458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0775    1.2599    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.3804    1.7011    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4138    2.5254    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7167    2.9665    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1444    2.9086    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8081    1.6431    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8416    2.4675    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5369    3.2341    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5722    2.8507    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2946   -0.3504    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.1006   -0.5265    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9066   -0.7026    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9245   -1.3325    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2767    0.2795    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7391   -0.9604    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9331   -0.7843    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3776   -1.3943    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6826    0.0017    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.1271   -0.6082    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8766    0.1778    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7005   -0.6282    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0906   -0.0727    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.2846    0.1034    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0341    0.8894    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7291   -0.5066    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0176    2.0494    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.3309    1.2862    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5218    2.7024    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.3394    2.5922    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2084    3.4655    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.7127    4.1185    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  3  2  1  1  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  1  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
  8 12  2  0  0  0  0
 13  7  1  6  0  0  0
 13 14  1  1  0  0  0
 13 15  1  0  0  0  0
 15 16  1  0  0  0  0
 17 16  1  6  0  0  0
 17 18  1  0  0  0  0
 18 19  1  6  0  0  0
 18 20  1  1  0  0  0
 20 21  1  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
 20 25  1  1  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 26 28  2  0  0  0  0
 18 29  1  0  0  0  0
 29 30  1  6  0  0  0
 30 31  1  0  0  0  0
 30 32  1  0  0  0  0
 30 33  1  0  0  0  0
 29 34  1  0  0  0  0
 34 35  1  0  0  0  0
 35 36  2  0  0  0  0
 35 37  1  0  0  0  0
 17 37  1  0  0  0  0
 37 38  1  6  0  0  0
 37 39  1  0  0  0  0
 13 39  1  0  0  0  0
 39 40  1  0  0  0  0
 40 41  1  0  0  0  0
 39 41  1  0  0  0  0
 41 42  1  6  0  0  0
 42 43  2  0  0  0  0
 42 44  1  0  0  0  0
  5 45  1  0  0  0  0
 45 46  1  6  0  0  0
 45 47  1  0  0  0  0
 47 48  1  1  0  0  0
 47 49  1  0  0  0  0
  3 49  1  0  0  0  0
 49 50  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0215786

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CO[C@H]1O[C@@H](OC(C2=COC=C2)[C@]2(C)CC[C@@H]3[C@@](C)([C@@H](CC(O)=O)OC(C)=O)[C@@H](CC(=O)[C@@]3(C)C22O[C@@H]2C(O)=O)C(C)(C)O)[C@H](O)[C@@H](O)[C@@H]1O

> <INCHI_IDENTIFIER>
InChI=1S/C34H48O16/c1-15(35)47-20(13-21(37)38)32(5)17-8-10-31(4,34(26(50-34)27(42)43)33(17,6)19(36)12-18(32)30(2,3)44)25(16-9-11-46-14-16)48-29-24(41)22(39)23(40)28(45-7)49-29/h9,11,14,17-18,20,22-26,28-29,39-41,44H,8,10,12-13H2,1-7H3,(H,37,38)(H,42,43)/t17-,18+,20-,22+,23+,24-,25?,26-,28+,29-,31+,32-,33+,34?/m1/s1

> <INCHI_KEY>
PBQZAYSJSIONKX-TYRRIYGBSA-N

> <FORMULA>
C34H48O16

> <MOLECULAR_WEIGHT>
712.742

> <EXACT_MASS>
712.294235466

> <JCHEM_ACCEPTOR_COUNT>
14

> <JCHEM_ATOM_COUNT>
98

> <JCHEM_AVERAGE_POLARIZABILITY>
70.97054853439872

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
6

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S,3'S,4aR,5R,6R,8aR)-5-[(1R)-1-(acetyloxy)-2-carboxyethyl]-2-[(furan-3-yl)({[(2R,3R,4S,5S,6S)-3,4,5-trihydroxy-6-methoxyoxan-2-yl]oxy})methyl]-6-(2-hydroxypropan-2-yl)-2,5,8a-trimethyl-8-oxo-octahydro-2H-spiro[naphthalene-1,2'-oxirane]-3'-carboxylic acid

> <JCHEM_LOGP>
0.8268437446666652

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
4.3606951934919875

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.6695346917365956

> <JCHEM_PKA_STRONGEST_BASIC>
-2.785487460925764

> <JCHEM_POLAR_SURFACE_AREA>
252.24999999999997

> <JCHEM_REFRACTIVITY>
164.82240000000004

> <JCHEM_ROTATABLE_BOND_COUNT>
12

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(2S,3'S,4aR,5R,6R,8aR)-5-[(1R)-1-(acetyloxy)-2-carboxyethyl]-2-[furan-3-yl({[(2R,3R,4S,5S,6S)-3,4,5-trihydroxy-6-methoxyoxan-2-yl]oxy})methyl]-6-(2-hydroxypropan-2-yl)-2,5,8a-trimethyl-8-oxo-tetrahydro-3H-spiro[naphthalene-1,2'-oxirane]-3'-carboxylic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 05-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   05-SEP-22         0                                  
HETATM    1  C   UNK     0       0.781   9.318   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       1.722   8.099   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       1.137   6.675   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       2.078   5.456   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       1.493   4.031   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       2.435   2.812   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       3.961   3.018   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.546   4.443   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       3.737   5.753   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.734   6.927   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       6.158   6.342   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       6.042   4.807   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.902   1.799   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       3.538   1.084   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       5.939   2.938   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       7.444   2.609   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       7.911   1.142   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       9.416   0.813   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      10.942   1.019   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       9.478   2.352   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       8.177   3.175   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       8.239   4.714   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       6.938   5.538   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0       9.603   5.429   0.000  0.00  0.00           O+0
HETATM   25  O   UNK     0      10.842   3.067   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0      10.904   4.606   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      10.335   6.037   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0      12.268   5.321   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0       9.883  -0.654   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      11.388  -0.983   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      12.892  -1.312   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      11.059  -2.487   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0      11.716   0.522   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0       8.846  -1.793   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       7.342  -1.464   0.000  0.00  0.00           C+0
HETATM   36  O   UNK     0       6.305  -2.603   0.000  0.00  0.00           O+0
HETATM   37  C   UNK     0       6.874   0.003   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0       5.837  -1.135   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0       5.370   0.332   0.000  0.00  0.00           C+0
HETATM   40  O   UNK     0       5.041  -1.173   0.000  0.00  0.00           O+0
HETATM   41  C   UNK     0       3.902  -0.136   0.000  0.00  0.00           C+0
HETATM   42  C   UNK     0       2.398   0.193   0.000  0.00  0.00           C+0
HETATM   43  O   UNK     0       1.930   1.660   0.000  0.00  0.00           O+0
HETATM   44  O   UNK     0       1.361  -0.946   0.000  0.00  0.00           O+0
HETATM   45  C   UNK     0      -0.033   3.826   0.000  0.00  0.00           C+0
HETATM   46  O   UNK     0      -0.618   2.401   0.000  0.00  0.00           O+0
HETATM   47  C   UNK     0      -0.974   5.044   0.000  0.00  0.00           C+0
HETATM   48  O   UNK     0      -2.500   4.839   0.000  0.00  0.00           O+0
HETATM   49  C   UNK     0      -0.389   6.469   0.000  0.00  0.00           C+0
HETATM   50  O   UNK     0      -1.330   7.688   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   49                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6   45                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8   13                                                  
CONECT    8    7    9   12                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11    8                                                       
CONECT   13    7   14   15   39                                             
CONECT   14   13                                                            
CONECT   15   13   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18   37                                                  
CONECT   18   17   19   20   29                                             
CONECT   19   18                                                            
CONECT   20   18   21   25                                                  
CONECT   21   20   22                                                       
CONECT   22   21   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22                                                            
CONECT   25   20   26                                                       
CONECT   26   25   27   28                                                  
CONECT   27   26                                                            
CONECT   28   26                                                            
CONECT   29   18   30   34                                                  
CONECT   30   29   31   32   33                                             
CONECT   31   30                                                            
CONECT   32   30                                                            
CONECT   33   30                                                            
CONECT   34   29   35                                                       
CONECT   35   34   36   37                                                  
CONECT   36   35                                                            
CONECT   37   35   17   38   39                                             
CONECT   38   37                                                            
CONECT   39   37   13   40   41                                             
CONECT   40   39   41                                                       
CONECT   41   40   39   42                                                  
CONECT   42   41   43   44                                                  
CONECT   43   42                                                            
CONECT   44   42                                                            
CONECT   45    5   46   47                                                  
CONECT   46   45                                                            
CONECT   47   45   48   49                                                  
CONECT   48   47                                                            
CONECT   49   47    3   50                                                  
CONECT   50   49                                                            
MASTER        0    0    0    0    0    0    0    0   50    0  108    0
END

View in JSmol

Synonyms

Value	Source
Nomilinate 17-b-D-glucopyranoside	Generator
Nomilinate 17-beta-D-glucopyranoside	Generator
Nomilinate 17-β-D-glucopyranoside	Generator
Nomilinic acid 17-b-D-glucopyranoside	Generator
Nomilinic acid 17-β-D-glucopyranoside	Generator

Chemical Formula

C₃₄H₄₈O₁₆

Average Mass

712.7420 Da

Monoisotopic Mass

712.29424 Da

IUPAC Name

(2S,3'S,4aR,5R,6R,8aR)-5-[(1R)-1-(acetyloxy)-2-carboxyethyl]-2-[(furan-3-yl)({[(2R,3R,4S,5S,6S)-3,4,5-trihydroxy-6-methoxyoxan-2-yl]oxy})methyl]-6-(2-hydroxypropan-2-yl)-2,5,8a-trimethyl-8-oxo-octahydro-2H-spiro[naphthalene-1,2'-oxirane]-3'-carboxylic acid

Traditional Name

(2S,3'S,4aR,5R,6R,8aR)-5-[(1R)-1-(acetyloxy)-2-carboxyethyl]-2-[furan-3-yl({[(2R,3R,4S,5S,6S)-3,4,5-trihydroxy-6-methoxyoxan-2-yl]oxy})methyl]-6-(2-hydroxypropan-2-yl)-2,5,8a-trimethyl-8-oxo-tetrahydro-3H-spiro[naphthalene-1,2'-oxirane]-3'-carboxylic acid

CAS Registry Number

Not Available

SMILES

CO[C@H]1O[C@@H](OC(C2=COC=C2)[C@]2(C)CC[C@@H]3[C@@](C)([C@@H](CC(O)=O)OC(C)=O)[C@@H](CC(=O)[C@@]3(C)C22O[C@@H]2C(O)=O)C(C)(C)O)[C@H](O)[C@@H](O)[C@@H]1O

InChI Identifier

InChI=1S/C34H48O16/c1-15(35)47-20(13-21(37)38)32(5)17-8-10-31(4,34(26(50-34)27(42)43)33(17,6)19(36)12-18(32)30(2,3)44)25(16-9-11-46-14-16)48-29-24(41)22(39)23(40)28(45-7)49-29/h9,11,14,17-18,20,22-26,28-29,39-41,44H,8,10,12-13H2,1-7H3,(H,37,38)(H,42,43)/t17-,18+,20-,22+,23+,24-,25?,26-,28+,29-,31+,32-,33+,34?/m1/s1

InChI Key

PBQZAYSJSIONKX-TYRRIYGBSA-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
Citrus hystrix	LOTUS Database	35616633
Citrus maxima	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Sesquiterpenoids

Direct Parent

Sesquiterpenoids

Alternative Parents

Substituents

Sesquiterpenoid
O-glycosyl compound
Glycosyl compound
Tricarboxylic acid or derivatives
Carbocyclic fatty acid
Hydroxy fatty acid
Fatty acyl
Oxirane carboxylic acid or derivatives
Oxirane carboxylic acid
Oxane
Monosaccharide
Heteroaromatic compound
Tertiary alcohol
Furan
Secondary alcohol
Ketone
Carboxylic acid ester
Oxacycle
Organoheterocyclic compound
Polyol
Ether
Oxirane
Dialkyl ether
Carboxylic acid
Carboxylic acid derivative
Acetal
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Alcohol
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	0.83	ChemAxon
pKa (Strongest Acidic)	3.67	ChemAxon
pKa (Strongest Basic)	-2.8	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	14	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	252.25 Å²	ChemAxon
Rotatable Bond Count	12	ChemAxon
Refractivity	164.82 m³·mol⁻¹	ChemAxon
Polarizability	70.97 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

44148128

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Raman G, Cho M, Brodbelt JS, Patil BS: Isolation and purification of closely related citrus limonoid glucosides by flash chromatography. Phytochem Anal. 2005 May-Jun;16(3):155-60. doi: 10.1002/pca.835. [PubMed:15997847 ]
Tian Q, Schwartz SJ: Mass spectrometry and tandem mass spectrometry of citrus limonoids. Anal Chem. 2003 Oct 15;75(20):5451-60. doi: 10.1021/ac030115w. [PubMed:14710824 ]
LOTUS database [Link]

Showing NP-Card for (2s,3's,4ar,5r,6r,8ar)-5-[(1r)-1-(acetyloxy)-2-carboxyethyl]-2-[furan-3-yl({[(2r,3r,4s,5s,6s)-3,4,5-trihydroxy-6-methoxyoxan-2-yl]oxy})methyl]-6-(2-hydroxypropan-2-yl)-2,5,8a-trimethyl-8-oxo-tetrahydro-3h-spiro[naphthalene-1,2'-oxirane]-3'-carboxylic acid (NP0215786)

MOL for NP0215786 ((2s,3's,4ar,5r,6r,8ar)-5-[(1r)-1-(acetyloxy)-2-carboxyethyl]-2-[furan-3-yl({[(2r,3r,4s,5s,6s)-3,4,5-trihydroxy-6-methoxyoxan-2-yl]oxy})methyl]-6-(2-hydroxypropan-2-yl)-2,5,8a-trimethyl-8-oxo-tetrahydro-3h-spiro[naphthalene-1,2'-oxirane]-3'-carboxylic acid)

3D MOL for NP0215786 ((2s,3's,4ar,5r,6r,8ar)-5-[(1r)-1-(acetyloxy)-2-carboxyethyl]-2-[furan-3-yl({[(2r,3r,4s,5s,6s)-3,4,5-trihydroxy-6-methoxyoxan-2-yl]oxy})methyl]-6-(2-hydroxypropan-2-yl)-2,5,8a-trimethyl-8-oxo-tetrahydro-3h-spiro[naphthalene-1,2'-oxirane]-3'-carboxylic acid)

3D SDF for NP0215786 ((2s,3's,4ar,5r,6r,8ar)-5-[(1r)-1-(acetyloxy)-2-carboxyethyl]-2-[furan-3-yl({[(2r,3r,4s,5s,6s)-3,4,5-trihydroxy-6-methoxyoxan-2-yl]oxy})methyl]-6-(2-hydroxypropan-2-yl)-2,5,8a-trimethyl-8-oxo-tetrahydro-3h-spiro[naphthalene-1,2'-oxirane]-3'-carboxylic acid)

3D-SDF for NP0215786 ((2s,3's,4ar,5r,6r,8ar)-5-[(1r)-1-(acetyloxy)-2-carboxyethyl]-2-[furan-3-yl({[(2r,3r,4s,5s,6s)-3,4,5-trihydroxy-6-methoxyoxan-2-yl]oxy})methyl]-6-(2-hydroxypropan-2-yl)-2,5,8a-trimethyl-8-oxo-tetrahydro-3h-spiro[naphthalene-1,2'-oxirane]-3'-carboxylic acid)

PDB for NP0215786 ((2s,3's,4ar,5r,6r,8ar)-5-[(1r)-1-(acetyloxy)-2-carboxyethyl]-2-[furan-3-yl({[(2r,3r,4s,5s,6s)-3,4,5-trihydroxy-6-methoxyoxan-2-yl]oxy})methyl]-6-(2-hydroxypropan-2-yl)-2,5,8a-trimethyl-8-oxo-tetrahydro-3h-spiro[naphthalene-1,2'-oxirane]-3'-carboxylic acid)

3D PDB for NP0215786 ((2s,3's,4ar,5r,6r,8ar)-5-[(1r)-1-(acetyloxy)-2-carboxyethyl]-2-[furan-3-yl({[(2r,3r,4s,5s,6s)-3,4,5-trihydroxy-6-methoxyoxan-2-yl]oxy})methyl]-6-(2-hydroxypropan-2-yl)-2,5,8a-trimethyl-8-oxo-tetrahydro-3h-spiro[naphthalene-1,2'-oxirane]-3'-carboxylic acid)

SMILES for NP0215786 ((2s,3's,4ar,5r,6r,8ar)-5-[(1r)-1-(acetyloxy)-2-carboxyethyl]-2-[furan-3-yl({[(2r,3r,4s,5s,6s)-3,4,5-trihydroxy-6-methoxyoxan-2-yl]oxy})methyl]-6-(2-hydroxypropan-2-yl)-2,5,8a-trimethyl-8-oxo-tetrahydro-3h-spiro[naphthalene-1,2'-oxirane]-3'-carboxylic acid)

INCHI for NP0215786 ((2s,3's,4ar,5r,6r,8ar)-5-[(1r)-1-(acetyloxy)-2-carboxyethyl]-2-[furan-3-yl({[(2r,3r,4s,5s,6s)-3,4,5-trihydroxy-6-methoxyoxan-2-yl]oxy})methyl]-6-(2-hydroxypropan-2-yl)-2,5,8a-trimethyl-8-oxo-tetrahydro-3h-spiro[naphthalene-1,2'-oxirane]-3'-carboxylic acid)

Structure for NP0215786 ((2s,3's,4ar,5r,6r,8ar)-5-[(1r)-1-(acetyloxy)-2-carboxyethyl]-2-[furan-3-yl({[(2r,3r,4s,5s,6s)-3,4,5-trihydroxy-6-methoxyoxan-2-yl]oxy})methyl]-6-(2-hydroxypropan-2-yl)-2,5,8a-trimethyl-8-oxo-tetrahydro-3h-spiro[naphthalene-1,2'-oxirane]-3'-carboxylic acid)

3D Structure for NP0215786 ((2s,3's,4ar,5r,6r,8ar)-5-[(1r)-1-(acetyloxy)-2-carboxyethyl]-2-[furan-3-yl({[(2r,3r,4s,5s,6s)-3,4,5-trihydroxy-6-methoxyoxan-2-yl]oxy})methyl]-6-(2-hydroxypropan-2-yl)-2,5,8a-trimethyl-8-oxo-tetrahydro-3h-spiro[naphthalene-1,2'-oxirane]-3'-carboxylic acid)