NP-MRD: Showing NP-Card for clinopodic acid I (NP0034637)

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Record Information

Version

2.0

Created at

2021-06-20 18:18:36 UTC

Updated at

2021-06-30 00:05:10 UTC

NP-MRD ID

NP0034637

Secondary Accession Numbers

None

Natural Product Identification

Common Name

clinopodic acid I

Provided By

JEOL Database JEOL Logo

Description

(2R)-2-[(2S,3S)-4-[(2R)-2-carboxy-2-{[3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy}ethyl]-2-(3,4-dihydroxyphenyl)-7-hydroxy-2,3-dihydro-1-benzofuran-3-carbonyloxy]-3-(3,4-dihydroxyphenyl)propanoic acid belongs to the class of organic compounds known as 2-arylbenzofuran flavonoids. These are phenylpropanoids containing the 2-phenylbenzofuran moiety. clinopodic acid I is found in Clinopodium chinense and Clinopodium chinense var. parviflorum. clinopodic acid I was first documented in 2009 (Murata, T., et al.). Based on a literature review very few articles have been published on (2R)-2-[(2S,3S)-4-[(2R)-2-carboxy-2-{[3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy}ethyl]-2-(3,4-dihydroxyphenyl)-7-hydroxy-2,3-dihydro-1-benzofuran-3-carbonyloxy]-3-(3,4-dihydroxyphenyl)propanoic acid.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306202120183D          

 82 86  0  0  0  0            999 V2000
   -5.1954    2.3990   -2.3417 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1731    1.7560   -2.1623 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6829    0.7604   -3.1357 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7982   -0.1999   -2.8262 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2503   -1.1830   -3.7727 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1020   -0.9057   -5.1432 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4949   -1.8293   -5.9983 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0290   -3.0250   -5.4779 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3840   -3.9028   -6.3001 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1753   -3.3199   -4.1261 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6854   -4.5181   -3.6855 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7769   -2.4058   -3.2678 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3301    1.8864   -1.1090 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7452    2.8618   -0.1367 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.5995    3.0895    0.8545 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.3532    3.6841    0.2414 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2692    5.0847    0.0961 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1393    5.6967   -0.4684 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9220    4.9156   -0.8947 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0137    5.5062   -1.4520 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8452    3.5447   -0.7498 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2647    2.9217   -0.1953 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0570    1.4420   -0.2794 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.2552    0.6686    0.9975 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2166    1.1339    2.1274 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5444   -0.6366    0.7162 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1501   -1.3605    1.8084 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.1281   -2.8597    1.4945 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.2117   -3.4845    1.8110 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4798   -3.9483    3.1115 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7209   -4.5046    3.4260 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6933   -4.5867    2.4424 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9110   -5.1229    2.7493 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4450   -4.1239    1.1535 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4609   -4.2214    0.2436 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2074   -3.5801    0.8271 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6102   -0.9410    1.9738 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2506   -0.9583    3.0121 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1830   -0.5692    0.8076 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4233    1.3868   -0.6934 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.6800    0.3629   -1.7855 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2839    0.6035   -3.1165 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4857   -0.3560   -4.1136 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0744   -1.5648   -3.7766 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2738   -2.5608   -4.6910 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4744   -1.8101   -2.4672 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0349   -3.0190   -2.1549 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2901   -0.8604   -1.4708 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8355    2.6960   -1.1717 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9213    2.3117    0.6651 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1941    1.1276    0.8238 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6469    3.2745    1.2666 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1235    0.8547   -4.1213 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4376   -0.2952   -1.8047 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4335    0.0411   -5.5627 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3770   -1.6089   -7.0551 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2049   -4.6826   -5.7347 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8521   -4.5871   -2.7293 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8723   -2.6292   -2.2094 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0276    3.7955   -0.6383 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9329    3.7512    1.6658 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3563    2.1470    1.3503 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0894    5.7205    0.4273 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0948    6.7773   -0.5714 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6336    4.7812   -1.6595 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7282    1.0549   -1.0510 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6209   -1.1462    2.7453 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8985   -3.3921    2.0678 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3636   -3.0338    0.4363 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2768   -3.8795    3.8911 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9288   -4.8650    4.4288 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4142   -5.0708    1.9117 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2024   -3.7484   -0.5769 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0101   -3.2297   -0.1805 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0986   -0.2546    1.0259 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0738    1.1657    0.1649 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8147    1.5494   -3.3847 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1753   -0.1443   -5.1319 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7367   -2.3605   -5.4813 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1217   -3.4601   -3.0302 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6188   -1.0755   -0.4573 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3720    2.8031    1.7297 H   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0  0  0  0
 32 33  1  0  0  0  0
  2 13  1  0  0  0  0
 22 16  2  0  0  0  0
 36 34  2  0  0  0  0
 17 18  2  0  0  0  0
 34 35  1  0  0  0  0
 18 19  1  0  0  0  0
 19 21  2  0  0  0  0
 19 20  1  0  0  0  0
 21 22  1  0  0  0  0
 34 32  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
 32 31  2  0  0  0  0
 10 11  1  0  0  0  0
 22 23  1  0  0  0  0
 23 40  1  0  0  0  0
 40 49  1  0  0  0  0
 49 21  1  0  0  0  0
 29 28  1  0  0  0  0
 40 41  1  0  0  0  0
 39 37  1  0  0  0  0
 41 48  2  0  0  0  0
 12  5  1  0  0  0  0
 48 46  1  0  0  0  0
 37 27  1  0  0  0  0
 46 44  2  0  0  0  0
  5  6  2  0  0  0  0
 44 43  1  0  0  0  0
 27 28  1  0  0  0  0
 43 42  2  0  0  0  0
 42 41  1  0  0  0  0
  6  7  1  0  0  0  0
 23 24  1  0  0  0  0
 24 26  1  0  0  0  0
 29 30  2  0  0  0  0
 24 25  2  0  0  0  0
  7  8  2  0  0  0  0
 44 45  1  0  0  0  0
 15 16  1  0  0  0  0
 37 38  2  0  0  0  0
  8 10  1  0  0  0  0
 10 12  2  0  0  0  0
 29 36  1  0  0  0  0
  8  9  1  0  0  0  0
 27 26  1  0  0  0  0
 15 14  1  0  0  0  0
 16 17  1  0  0  0  0
 52 50  1  0  0  0  0
 50 14  1  0  0  0  0
  3  2  1  0  0  0  0
 50 51  2  0  0  0  0
 14 13  1  0  0  0  0
 31 30  1  0  0  0  0
 46 47  1  0  0  0  0
 31 71  1  0  0  0  0
 36 74  1  0  0  0  0
 30 70  1  0  0  0  0
 39 75  1  0  0  0  0
 27 67  1  1  0  0  0
 28 68  1  0  0  0  0
 28 69  1  0  0  0  0
 33 72  1  0  0  0  0
 35 73  1  0  0  0  0
  3 53  1  0  0  0  0
  4 54  1  0  0  0  0
 11 58  1  0  0  0  0
 12 59  1  0  0  0  0
  6 55  1  0  0  0  0
  7 56  1  0  0  0  0
  9 57  1  0  0  0  0
 18 64  1  0  0  0  0
 20 65  1  0  0  0  0
 23 66  1  6  0  0  0
 40 76  1  1  0  0  0
 48 81  1  0  0  0  0
 43 78  1  0  0  0  0
 42 77  1  0  0  0  0
 45 79  1  0  0  0  0
 15 61  1  0  0  0  0
 15 62  1  0  0  0  0
 17 63  1  0  0  0  0
 52 82  1  0  0  0  0
 14 60  1  6  0  0  0
 47 80  1  0  0  0  0
M  END

     RDKit          3D

 82 86  0  0  0  0  0  0  0  0999 V2000
   -5.1954    2.3990   -2.3417 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1731    1.7560   -2.1623 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6829    0.7604   -3.1357 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7982   -0.1999   -2.8262 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2503   -1.1830   -3.7727 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1020   -0.9057   -5.1432 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4949   -1.8293   -5.9983 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0290   -3.0250   -5.4779 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3840   -3.9028   -6.3001 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1753   -3.3199   -4.1261 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6854   -4.5181   -3.6855 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7769   -2.4058   -3.2678 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3301    1.8864   -1.1090 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7452    2.8618   -0.1367 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.5995    3.0895    0.8545 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3532    3.6841    0.2414 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2692    5.0847    0.0961 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1393    5.6967   -0.4684 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9220    4.9156   -0.8947 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0137    5.5062   -1.4520 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8452    3.5447   -0.7498 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2647    2.9217   -0.1953 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0570    1.4420   -0.2794 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.2552    0.6686    0.9975 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2166    1.1339    2.1274 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5444   -0.6366    0.7162 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1501   -1.3605    1.8084 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.1281   -2.8597    1.4945 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2117   -3.4845    1.8110 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4798   -3.9483    3.1115 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7209   -4.5046    3.4260 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6933   -4.5867    2.4424 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9110   -5.1229    2.7493 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4450   -4.1239    1.1535 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4609   -4.2214    0.2436 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2074   -3.5801    0.8271 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6102   -0.9410    1.9738 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2506   -0.9583    3.0121 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1830   -0.5692    0.8076 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4233    1.3868   -0.6934 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.6800    0.3629   -1.7855 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2839    0.6035   -3.1165 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4857   -0.3560   -4.1136 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0744   -1.5648   -3.7766 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2738   -2.5608   -4.6910 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4744   -1.8101   -2.4672 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0349   -3.0190   -2.1549 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2901   -0.8604   -1.4708 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8355    2.6960   -1.1717 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9213    2.3117    0.6651 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1941    1.1276    0.8238 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6469    3.2745    1.2666 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1235    0.8547   -4.1213 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4376   -0.2952   -1.8047 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4335    0.0411   -5.5627 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3770   -1.6089   -7.0551 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2049   -4.6826   -5.7347 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8521   -4.5871   -2.7293 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8723   -2.6292   -2.2094 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0276    3.7955   -0.6383 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9329    3.7512    1.6658 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3563    2.1470    1.3503 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0894    5.7205    0.4273 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0948    6.7773   -0.5714 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6336    4.7812   -1.6595 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7282    1.0549   -1.0510 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6209   -1.1462    2.7453 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8985   -3.3921    2.0678 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3636   -3.0338    0.4363 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2768   -3.8795    3.8911 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9288   -4.8650    4.4288 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4142   -5.0708    1.9117 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2024   -3.7484   -0.5769 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0101   -3.2297   -0.1805 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0986   -0.2546    1.0259 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0738    1.1657    0.1649 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8147    1.5494   -3.3847 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1753   -0.1443   -5.1319 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7367   -2.3605   -5.4813 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1217   -3.4601   -3.0302 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6188   -1.0755   -0.4573 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3720    2.8031    1.7297 H   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0
 32 33  1  0
  2 13  1  0
 22 16  2  0
 36 34  2  0
 17 18  2  0
 34 35  1  0
 18 19  1  0
 19 21  2  0
 19 20  1  0
 21 22  1  0
 34 32  1  0
  3  4  2  0
  4  5  1  0
 32 31  2  0
 10 11  1  0
 22 23  1  0
 23 40  1  0
 40 49  1  0
 49 21  1  0
 29 28  1  0
 40 41  1  0
 39 37  1  0
 41 48  2  0
 12  5  1  0
 48 46  1  0
 37 27  1  0
 46 44  2  0
  5  6  2  0
 44 43  1  0
 27 28  1  0
 43 42  2  0
 42 41  1  0
  6  7  1  0
 23 24  1  0
 24 26  1  0
 29 30  2  0
 24 25  2  0
  7  8  2  0
 44 45  1  0
 15 16  1  0
 37 38  2  0
  8 10  1  0
 10 12  2  0
 29 36  1  0
  8  9  1  0
 27 26  1  0
 15 14  1  0
 16 17  1  0
 52 50  1  0
 50 14  1  0
  3  2  1  0
 50 51  2  0
 14 13  1  0
 31 30  1  0
 46 47  1  0
 31 71  1  0
 36 74  1  0
 30 70  1  0
 39 75  1  0
 27 67  1  1
 28 68  1  0
 28 69  1  0
 33 72  1  0
 35 73  1  0
  3 53  1  0
  4 54  1  0
 11 58  1  0
 12 59  1  0
  6 55  1  0
  7 56  1  0
  9 57  1  0
 18 64  1  0
 20 65  1  0
 23 66  1  6
 40 76  1  1
 48 81  1  0
 43 78  1  0
 42 77  1  0
 45 79  1  0
 15 61  1  0
 15 62  1  0
 17 63  1  0
 52 82  1  0
 14 60  1  6
 47 80  1  0
M  END


  Mrv1652306202120183D          

 82 86  0  0  0  0            999 V2000
   -5.1954    2.3990   -2.3417 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1731    1.7560   -2.1623 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6829    0.7604   -3.1357 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7982   -0.1999   -2.8262 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2503   -1.1830   -3.7727 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1020   -0.9057   -5.1432 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4949   -1.8293   -5.9983 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0290   -3.0250   -5.4779 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3840   -3.9028   -6.3001 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1753   -3.3199   -4.1261 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6854   -4.5181   -3.6855 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7769   -2.4058   -3.2678 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3301    1.8864   -1.1090 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7452    2.8618   -0.1367 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.5995    3.0895    0.8545 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.3532    3.6841    0.2414 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2692    5.0847    0.0961 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1393    5.6967   -0.4684 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9220    4.9156   -0.8947 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0137    5.5062   -1.4520 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8452    3.5447   -0.7498 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2647    2.9217   -0.1953 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0570    1.4420   -0.2794 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.2552    0.6686    0.9975 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2166    1.1339    2.1274 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5444   -0.6366    0.7162 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1501   -1.3605    1.8084 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.1281   -2.8597    1.4945 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.2117   -3.4845    1.8110 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4798   -3.9483    3.1115 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7209   -4.5046    3.4260 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6933   -4.5867    2.4424 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9110   -5.1229    2.7493 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4450   -4.1239    1.1535 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4609   -4.2214    0.2436 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2074   -3.5801    0.8271 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6102   -0.9410    1.9738 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2506   -0.9583    3.0121 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1830   -0.5692    0.8076 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4233    1.3868   -0.6934 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.6800    0.3629   -1.7855 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2839    0.6035   -3.1165 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4857   -0.3560   -4.1136 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0744   -1.5648   -3.7766 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2738   -2.5608   -4.6910 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4744   -1.8101   -2.4672 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0349   -3.0190   -2.1549 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2901   -0.8604   -1.4708 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8355    2.6960   -1.1717 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9213    2.3117    0.6651 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1941    1.1276    0.8238 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6469    3.2745    1.2666 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1235    0.8547   -4.1213 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4376   -0.2952   -1.8047 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4335    0.0411   -5.5627 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3770   -1.6089   -7.0551 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2049   -4.6826   -5.7347 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8521   -4.5871   -2.7293 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8723   -2.6292   -2.2094 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0276    3.7955   -0.6383 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9329    3.7512    1.6658 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3563    2.1470    1.3503 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0894    5.7205    0.4273 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0948    6.7773   -0.5714 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6336    4.7812   -1.6595 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7282    1.0549   -1.0510 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6209   -1.1462    2.7453 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8985   -3.3921    2.0678 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3636   -3.0338    0.4363 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2768   -3.8795    3.8911 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9288   -4.8650    4.4288 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4142   -5.0708    1.9117 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2024   -3.7484   -0.5769 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0101   -3.2297   -0.1805 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0986   -0.2546    1.0259 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0738    1.1657    0.1649 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8147    1.5494   -3.3847 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1753   -0.1443   -5.1319 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7367   -2.3605   -5.4813 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1217   -3.4601   -3.0302 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6188   -1.0755   -0.4573 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3720    2.8031    1.7297 H   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0  0  0  0
 32 33  1  0  0  0  0
  2 13  1  0  0  0  0
 22 16  2  0  0  0  0
 36 34  2  0  0  0  0
 17 18  2  0  0  0  0
 34 35  1  0  0  0  0
 18 19  1  0  0  0  0
 19 21  2  0  0  0  0
 19 20  1  0  0  0  0
 21 22  1  0  0  0  0
 34 32  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
 32 31  2  0  0  0  0
 10 11  1  0  0  0  0
 22 23  1  0  0  0  0
 23 40  1  0  0  0  0
 40 49  1  0  0  0  0
 49 21  1  0  0  0  0
 29 28  1  0  0  0  0
 40 41  1  0  0  0  0
 39 37  1  0  0  0  0
 41 48  2  0  0  0  0
 12  5  1  0  0  0  0
 48 46  1  0  0  0  0
 37 27  1  0  0  0  0
 46 44  2  0  0  0  0
  5  6  2  0  0  0  0
 44 43  1  0  0  0  0
 27 28  1  0  0  0  0
 43 42  2  0  0  0  0
 42 41  1  0  0  0  0
  6  7  1  0  0  0  0
 23 24  1  0  0  0  0
 24 26  1  0  0  0  0
 29 30  2  0  0  0  0
 24 25  2  0  0  0  0
  7  8  2  0  0  0  0
 44 45  1  0  0  0  0
 15 16  1  0  0  0  0
 37 38  2  0  0  0  0
  8 10  1  0  0  0  0
 10 12  2  0  0  0  0
 29 36  1  0  0  0  0
  8  9  1  0  0  0  0
 27 26  1  0  0  0  0
 15 14  1  0  0  0  0
 16 17  1  0  0  0  0
 52 50  1  0  0  0  0
 50 14  1  0  0  0  0
  3  2  1  0  0  0  0
 50 51  2  0  0  0  0
 14 13  1  0  0  0  0
 31 30  1  0  0  0  0
 46 47  1  0  0  0  0
 31 71  1  0  0  0  0
 36 74  1  0  0  0  0
 30 70  1  0  0  0  0
 39 75  1  0  0  0  0
 27 67  1  1  0  0  0
 28 68  1  0  0  0  0
 28 69  1  0  0  0  0
 33 72  1  0  0  0  0
 35 73  1  0  0  0  0
  3 53  1  0  0  0  0
  4 54  1  0  0  0  0
 11 58  1  0  0  0  0
 12 59  1  0  0  0  0
  6 55  1  0  0  0  0
  7 56  1  0  0  0  0
  9 57  1  0  0  0  0
 18 64  1  0  0  0  0
 20 65  1  0  0  0  0
 23 66  1  6  0  0  0
 40 76  1  1  0  0  0
 48 81  1  0  0  0  0
 43 78  1  0  0  0  0
 42 77  1  0  0  0  0
 45 79  1  0  0  0  0
 15 61  1  0  0  0  0
 15 62  1  0  0  0  0
 17 63  1  0  0  0  0
 52 82  1  0  0  0  0
 14 60  1  6  0  0  0
 47 80  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0034637

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC(=O)[C@]([H])(OC(=O)C(\[H])=C(/[H])C1=C([H])C([H])=C(O[H])C(O[H])=C1[H])C([H])([H])C1=C2C(O[C@]([H])(C3=C([H])C(O[H])=C(O[H])C([H])=C3[H])[C@@]2([H])C(=O)O[C@@]([H])(C(=O)O[H])C([H])([H])C2=C([H])C([H])=C(O[H])C(O[H])=C2[H])=C(O[H])C([H])=C1[H]

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

> <INCHI_KEY>
ABOFMZGCFQOHLN-BPEDTOSASA-N

> <FORMULA>
C36H30O16

> <MOLECULAR_WEIGHT>
718.62

> <EXACT_MASS>
718.153384886

> <JCHEM_ACCEPTOR_COUNT>
14

> <JCHEM_ATOM_COUNT>
82

> <JCHEM_AVERAGE_POLARIZABILITY>
68.16322648009708

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
9

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

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

> <ALOGPS_LOGP>
3.88

> <JCHEM_LOGP>
4.987507691666666

> <ALOGPS_LOGS>
-4.39

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
3.3329350517228704

> <JCHEM_PKA_STRONGEST_ACIDIC>
2.7302927820792595

> <JCHEM_PKA_STRONGEST_BASIC>
-5.1149148570367595

> <JCHEM_POLAR_SURFACE_AREA>
278.03999999999996

> <JCHEM_REFRACTIVITY>
177.00090000000003

> <JCHEM_ROTATABLE_BOND_COUNT>
14

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.90e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
clinopodic acid I

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 82 86  0  0  0  0  0  0  0  0999 V2000
   -5.1954    2.3990   -2.3417 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1731    1.7560   -2.1623 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6829    0.7604   -3.1357 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7982   -0.1999   -2.8262 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2503   -1.1830   -3.7727 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1020   -0.9057   -5.1432 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4949   -1.8293   -5.9983 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0290   -3.0250   -5.4779 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3840   -3.9028   -6.3001 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1753   -3.3199   -4.1261 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6854   -4.5181   -3.6855 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7769   -2.4058   -3.2678 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3301    1.8864   -1.1090 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7452    2.8618   -0.1367 C   0  0  2  0  0  0  0  0  0  0  0  0
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    1.2839    0.6035   -3.1165 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4857   -0.3560   -4.1136 C   0  0  0  0  0  0  0  0  0  0  0  0
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    2.2738   -2.5608   -4.6910 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -5.6469    3.2745    1.2666 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1235    0.8547   -4.1213 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4376   -0.2952   -1.8047 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4335    0.0411   -5.5627 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3770   -1.6089   -7.0551 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2049   -4.6826   -5.7347 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8521   -4.5871   -2.7293 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8723   -2.6292   -2.2094 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0276    3.7955   -0.6383 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.6209   -1.1462    2.7453 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8985   -3.3921    2.0678 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3636   -3.0338    0.4363 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2768   -3.8795    3.8911 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9288   -4.8650    4.4288 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4142   -5.0708    1.9117 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2024   -3.7484   -0.5769 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0101   -3.2297   -0.1805 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0986   -0.2546    1.0259 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0738    1.1657    0.1649 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8147    1.5494   -3.3847 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1753   -0.1443   -5.1319 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7367   -2.3605   -5.4813 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1217   -3.4601   -3.0302 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6188   -1.0755   -0.4573 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3720    2.8031    1.7297 H   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0
 32 33  1  0
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 18 64  1  0
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 15 61  1  0
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 17 63  1  0
 52 82  1  0
 14 60  1  6
 47 80  1  0
M  END

HEADER    PROTEIN                                 20-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   20-JUN-21         0                                  
HETATM    1  O   UNK     0      -5.195   2.399  -2.342  0.00  0.00           O+0
HETATM    2  C   UNK     0      -4.173   1.756  -2.162  0.00  0.00           C+0
HETATM    3  C   UNK     0      -3.683   0.760  -3.136  0.00  0.00           C+0
HETATM    4  C   UNK     0      -2.798  -0.200  -2.826  0.00  0.00           C+0
HETATM    5  C   UNK     0      -2.250  -1.183  -3.773  0.00  0.00           C+0
HETATM    6  C   UNK     0      -2.102  -0.906  -5.143  0.00  0.00           C+0
HETATM    7  C   UNK     0      -1.495  -1.829  -5.998  0.00  0.00           C+0
HETATM    8  C   UNK     0      -1.029  -3.025  -5.478  0.00  0.00           C+0
HETATM    9  O   UNK     0      -0.384  -3.903  -6.300  0.00  0.00           O+0
HETATM   10  C   UNK     0      -1.175  -3.320  -4.126  0.00  0.00           C+0
HETATM   11  O   UNK     0      -0.685  -4.518  -3.686  0.00  0.00           O+0
HETATM   12  C   UNK     0      -1.777  -2.406  -3.268  0.00  0.00           C+0
HETATM   13  O   UNK     0      -3.330   1.886  -1.109  0.00  0.00           O+0
HETATM   14  C   UNK     0      -3.745   2.862  -0.137  0.00  0.00           C+0
HETATM   15  C   UNK     0      -2.599   3.090   0.855  0.00  0.00           C+0
HETATM   16  C   UNK     0      -1.353   3.684   0.241  0.00  0.00           C+0
HETATM   17  C   UNK     0      -1.269   5.085   0.096  0.00  0.00           C+0
HETATM   18  C   UNK     0      -0.139   5.697  -0.468  0.00  0.00           C+0
HETATM   19  C   UNK     0       0.922   4.916  -0.895  0.00  0.00           C+0
HETATM   20  O   UNK     0       2.014   5.506  -1.452  0.00  0.00           O+0
HETATM   21  C   UNK     0       0.845   3.545  -0.750  0.00  0.00           C+0
HETATM   22  C   UNK     0      -0.265   2.922  -0.195  0.00  0.00           C+0
HETATM   23  C   UNK     0      -0.057   1.442  -0.279  0.00  0.00           C+0
HETATM   24  C   UNK     0      -0.255   0.669   0.998  0.00  0.00           C+0
HETATM   25  O   UNK     0      -0.217   1.134   2.127  0.00  0.00           O+0
HETATM   26  O   UNK     0      -0.544  -0.637   0.716  0.00  0.00           O+0
HETATM   27  C   UNK     0      -1.150  -1.361   1.808  0.00  0.00           C+0
HETATM   28  C   UNK     0      -1.128  -2.860   1.494  0.00  0.00           C+0
HETATM   29  C   UNK     0       0.212  -3.485   1.811  0.00  0.00           C+0
HETATM   30  C   UNK     0       0.480  -3.948   3.111  0.00  0.00           C+0
HETATM   31  C   UNK     0       1.721  -4.505   3.426  0.00  0.00           C+0
HETATM   32  C   UNK     0       2.693  -4.587   2.442  0.00  0.00           C+0
HETATM   33  O   UNK     0       3.911  -5.123   2.749  0.00  0.00           O+0
HETATM   34  C   UNK     0       2.445  -4.124   1.153  0.00  0.00           C+0
HETATM   35  O   UNK     0       3.461  -4.221   0.244  0.00  0.00           O+0
HETATM   36  C   UNK     0       1.207  -3.580   0.827  0.00  0.00           C+0
HETATM   37  C   UNK     0      -2.610  -0.941   1.974  0.00  0.00           C+0
HETATM   38  O   UNK     0      -3.251  -0.958   3.012  0.00  0.00           O+0
HETATM   39  O   UNK     0      -3.183  -0.569   0.808  0.00  0.00           O+0
HETATM   40  C   UNK     0       1.423   1.387  -0.693  0.00  0.00           C+0
HETATM   41  C   UNK     0       1.680   0.363  -1.786  0.00  0.00           C+0
HETATM   42  C   UNK     0       1.284   0.604  -3.116  0.00  0.00           C+0
HETATM   43  C   UNK     0       1.486  -0.356  -4.114  0.00  0.00           C+0
HETATM   44  C   UNK     0       2.074  -1.565  -3.777  0.00  0.00           C+0
HETATM   45  O   UNK     0       2.274  -2.561  -4.691  0.00  0.00           O+0
HETATM   46  C   UNK     0       2.474  -1.810  -2.467  0.00  0.00           C+0
HETATM   47  O   UNK     0       3.035  -3.019  -2.155  0.00  0.00           O+0
HETATM   48  C   UNK     0       2.290  -0.860  -1.471  0.00  0.00           C+0
HETATM   49  O   UNK     0       1.835   2.696  -1.172  0.00  0.00           O+0
HETATM   50  C   UNK     0      -4.921   2.312   0.665  0.00  0.00           C+0
HETATM   51  O   UNK     0      -5.194   1.128   0.824  0.00  0.00           O+0
HETATM   52  O   UNK     0      -5.647   3.275   1.267  0.00  0.00           O+0
HETATM   53  H   UNK     0      -4.123   0.855  -4.121  0.00  0.00           H+0
HETATM   54  H   UNK     0      -2.438  -0.295  -1.805  0.00  0.00           H+0
HETATM   55  H   UNK     0      -2.434   0.041  -5.563  0.00  0.00           H+0
HETATM   56  H   UNK     0      -1.377  -1.609  -7.055  0.00  0.00           H+0
HETATM   57  H   UNK     0      -0.205  -4.683  -5.735  0.00  0.00           H+0
HETATM   58  H   UNK     0      -0.852  -4.587  -2.729  0.00  0.00           H+0
HETATM   59  H   UNK     0      -1.872  -2.629  -2.209  0.00  0.00           H+0
HETATM   60  H   UNK     0      -4.028   3.796  -0.638  0.00  0.00           H+0
HETATM   61  H   UNK     0      -2.933   3.751   1.666  0.00  0.00           H+0
HETATM   62  H   UNK     0      -2.356   2.147   1.350  0.00  0.00           H+0
HETATM   63  H   UNK     0      -2.089   5.721   0.427  0.00  0.00           H+0
HETATM   64  H   UNK     0      -0.095   6.777  -0.571  0.00  0.00           H+0
HETATM   65  H   UNK     0       2.634   4.781  -1.660  0.00  0.00           H+0
HETATM   66  H   UNK     0      -0.728   1.055  -1.051  0.00  0.00           H+0
HETATM   67  H   UNK     0      -0.621  -1.146   2.745  0.00  0.00           H+0
HETATM   68  H   UNK     0      -1.899  -3.392   2.068  0.00  0.00           H+0
HETATM   69  H   UNK     0      -1.364  -3.034   0.436  0.00  0.00           H+0
HETATM   70  H   UNK     0      -0.277  -3.880   3.891  0.00  0.00           H+0
HETATM   71  H   UNK     0       1.929  -4.865   4.429  0.00  0.00           H+0
HETATM   72  H   UNK     0       4.414  -5.071   1.912  0.00  0.00           H+0
HETATM   73  H   UNK     0       3.202  -3.748  -0.577  0.00  0.00           H+0
HETATM   74  H   UNK     0       1.010  -3.230  -0.181  0.00  0.00           H+0
HETATM   75  H   UNK     0      -4.099  -0.255   1.026  0.00  0.00           H+0
HETATM   76  H   UNK     0       2.074   1.166   0.165  0.00  0.00           H+0
HETATM   77  H   UNK     0       0.815   1.549  -3.385  0.00  0.00           H+0
HETATM   78  H   UNK     0       1.175  -0.144  -5.132  0.00  0.00           H+0
HETATM   79  H   UNK     0       1.737  -2.361  -5.481  0.00  0.00           H+0
HETATM   80  H   UNK     0       3.122  -3.460  -3.030  0.00  0.00           H+0
HETATM   81  H   UNK     0       2.619  -1.075  -0.457  0.00  0.00           H+0
HETATM   82  H   UNK     0      -6.372   2.803   1.730  0.00  0.00           H+0
CONECT    1    2                                                            
CONECT    2    1   13    3                                                  
CONECT    3    4    2   53                                                  
CONECT    4    3    5   54                                                  
CONECT    5    4   12    6                                                  
CONECT    6    5    7   55                                                  
CONECT    7    6    8   56                                                  
CONECT    8    7   10    9                                                  
CONECT    9    8   57                                                       
CONECT   10   11    8   12                                                  
CONECT   11   10   58                                                       
CONECT   12    5   10   59                                                  
CONECT   13    2   14                                                       
CONECT   14   15   50   13   60                                             
CONECT   15   16   14   61   62                                             
CONECT   16   22   15   17                                                  
CONECT   17   18   16   63                                                  
CONECT   18   17   19   64                                                  
CONECT   19   18   21   20                                                  
CONECT   20   19   65                                                       
CONECT   21   19   22   49                                                  
CONECT   22   16   21   23                                                  
CONECT   23   22   40   24   66                                             
CONECT   24   23   26   25                                                  
CONECT   25   24                                                            
CONECT   26   24   27                                                       
CONECT   27   37   28   26   67                                             
CONECT   28   29   27   68   69                                             
CONECT   29   28   30   36                                                  
CONECT   30   29   31   70                                                  
CONECT   31   32   30   71                                                  
CONECT   32   33   34   31                                                  
CONECT   33   32   72                                                       
CONECT   34   36   35   32                                                  
CONECT   35   34   73                                                       
CONECT   36   34   29   74                                                  
CONECT   37   39   27   38                                                  
CONECT   38   37                                                            
CONECT   39   37   75                                                       
CONECT   40   23   49   41   76                                             
CONECT   41   40   48   42                                                  
CONECT   42   43   41   77                                                  
CONECT   43   44   42   78                                                  
CONECT   44   46   43   45                                                  
CONECT   45   44   79                                                       
CONECT   46   48   44   47                                                  
CONECT   47   46   80                                                       
CONECT   48   41   46   81                                                  
CONECT   49   40   21                                                       
CONECT   50   52   14   51                                                  
CONECT   51   50                                                            
CONECT   52   50   82                                                       
CONECT   53    3                                                            
CONECT   54    4                                                            
CONECT   55    6                                                            
CONECT   56    7                                                            
CONECT   57    9                                                            
CONECT   58   11                                                            
CONECT   59   12                                                            
CONECT   60   14                                                            
CONECT   61   15                                                            
CONECT   62   15                                                            
CONECT   63   17                                                            
CONECT   64   18                                                            
CONECT   65   20                                                            
CONECT   66   23                                                            
CONECT   67   27                                                            
CONECT   68   28                                                            
CONECT   69   28                                                            
CONECT   70   30                                                            
CONECT   71   31                                                            
CONECT   72   33                                                            
CONECT   73   35                                                            
CONECT   74   36                                                            
CONECT   75   39                                                            
CONECT   76   40                                                            
CONECT   77   42                                                            
CONECT   78   43                                                            
CONECT   79   45                                                            
CONECT   80   47                                                            
CONECT   81   48                                                            
CONECT   82   52                                                            
MASTER        0    0    0    0    0    0    0    0   82    0  172    0
END

RDKit          3D

82 86  0  0  0  0  0  0  0  0999 V2000
   -5.1954    2.3990   -2.3417 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1731    1.7560   -2.1623 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6829    0.7604   -3.1357 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7982   -0.1999   -2.8262 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2503   -1.1830   -3.7727 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1020   -0.9057   -5.1432 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4949   -1.8293   -5.9983 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0290   -3.0250   -5.4779 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3840   -3.9028   -6.3001 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1753   -3.3199   -4.1261 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6854   -4.5181   -3.6855 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7769   -2.4058   -3.2678 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -6.3720    2.8031    1.7297 H   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0
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M  END

View in JSmol

Synonyms

Value	Source
(2R)-2-[(2S,3S)-4-[(2R)-2-Carboxy-2-{[3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy}ethyl]-2-(3,4-dihydroxyphenyl)-7-hydroxy-2,3-dihydro-1-benzofuran-3-carbonyloxy]-3-(3,4-dihydroxyphenyl)propanoate	Generator

Chemical Formula

C₃₆H₃₀O₁₆

Average Mass

718.6200 Da

Monoisotopic Mass

718.15338 Da

IUPAC Name

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

Traditional Name

clinopodic acid I

CAS Registry Number

Not Available

SMILES

[H]OC(=O)[C@]([H])(OC(=O)C(\[H])=C(/[H])C1=C([H])C([H])=C(O[H])C(O[H])=C1[H])C([H])([H])C1=C2C(O[C@]([H])(C3=C([H])C(O[H])=C(O[H])C([H])=C3[H])[C@@]2([H])C(=O)O[C@@]([H])(C(=O)O[H])C([H])([H])C2=C([H])C([H])=C(O[H])C(O[H])=C2[H])=C(O[H])C([H])=C1[H]

InChI Identifier

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

InChI Key

ABOFMZGCFQOHLN-BPEDTOSASA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, acetone-d6, 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
Clinopodium chinense	LOTUS Database	35616633
Clinopodium chinense var. parviflorum	JEOL database	Murata, T., et al, J. Nat. Prod. 72, 1379 (2009)

Chemical Taxonomy

Description

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

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

2-arylbenzofuran flavonoids

Sub Class

Not Available

Direct Parent

2-arylbenzofuran flavonoids

Alternative Parents

Substituents

2-arylbenzofuran flavonoid
Tetracarboxylic acid or derivatives
Cinnamic acid or derivatives
Coumaric acid or derivatives
Hydroxycinnamic acid or derivatives
Cinnamic acid ester
3-phenylpropanoic-acid
Coumaran
Catechol
Styrene
Alkyl aryl ether
1-hydroxy-4-unsubstituted benzenoid
Phenol
1-hydroxy-2-unsubstituted benzenoid
Fatty acid ester
Fatty acyl
Benzenoid
Monocyclic benzene moiety
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Carboxylic acid ester
Ether
Carboxylic acid
Organoheterocyclic compound
Carboxylic acid derivative
Oxacycle
Organooxygen compound
Organic oxide
Carbonyl group
Hydrocarbon derivative
Organic oxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	3.88	ALOGPS
logP	4.99	ChemAxon
logS	-4.4	ALOGPS
pKa (Strongest Acidic)	2.73	ChemAxon
pKa (Strongest Basic)	-5.1	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	14	ChemAxon
Hydrogen Donor Count	9	ChemAxon
Polar Surface Area	278.04 Å²	ChemAxon
Rotatable Bond Count	14	ChemAxon
Refractivity	177 m³·mol⁻¹	ChemAxon
Polarizability	68.16 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

44254599

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Murata, T., et al. (2009). Murata, T., et al, J. Nat. Prod. 72, 1379 (2009). J. Nat. Prod..

Showing NP-Card for clinopodic acid I (NP0034637)

MOL for NP0034637 (clinopodic acid I)

3D MOL for NP0034637 (clinopodic acid I)

3D SDF for NP0034637 (clinopodic acid I)

3D-SDF for NP0034637 (clinopodic acid I)

PDB for NP0034637 (clinopodic acid I)

3D PDB for NP0034637 (clinopodic acid I)

SMILES for NP0034637 (clinopodic acid I)

INCHI for NP0034637 (clinopodic acid I)

Structure for NP0034637 (clinopodic acid I)

3D Structure for NP0034637 (clinopodic acid I)