NP-MRD: Showing NP-Card for N-trans-grossamide (NP0031588)

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Record Information

Version

1.0

Created at

2021-06-19 22:37:35 UTC

Updated at

2021-06-30 00:00:15 UTC

NP-MRD ID

NP0031588

Secondary Accession Numbers

None

Natural Product Identification

Common Name

N-trans-grossamide

Provided By

JEOL Database JEOL Logo

Description

GROSSAMIDE belongs to the class of organic compounds known as 2-arylbenzofuran flavonoids. These are phenylpropanoids containing the 2-phenylbenzofuran moiety. N-trans-grossamide is found in Cannabis sativa , Capsicum annuum var.grossum , Hibiscus cannabinus, Hyoscyamus niger , Nicotiana tabacum , Solanum tuberosum and Xylopia aethiopica . It was first documented in 2017 (PMID: 28224333). Based on a literature review a significant number of articles have been published on GROSSAMIDE (PMID: 32877711) (PMID: 32222655) (PMID: 31350127) (PMID: 29676594).

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306202100433D          

 82 86  0  0  0  0            999 V2000
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M  END

     RDKit          3D

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   -0.3053   -0.4315   -0.5535 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2649   -3.3100   -0.9902 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7180   -1.3948   -0.8421 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4220   -1.0970   -2.2873 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0605   -2.6657   -3.0223 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3145   -1.6620   -4.4635 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8538   -0.8726   -4.7135 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3133    1.3591   -3.3939 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2853    3.5381   -2.9132 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3410    4.6768   -2.7650 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6292    1.8257   -3.4487 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3943   -0.3743   -3.9206 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1758   -5.1354    2.3946 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7712   -7.0165    2.4862 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3523   -9.0125   -0.3675 H   0  0  0  0  0  0  0  0  0  0  0  0
 15 16  1  0
 29 30  1  0
 16 18  1  0
  5  4  1  0
 18 19  1  0
  8 29  2  0
 19 20  1  0
  4  3  2  0
 20 21  1  0
  8  9  1  0
 16 17  2  0
  3 45  1  0
 21 22  2  0
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 23 24  2  0
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 43  5  2  0
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  2  1  1  0
 31 33  1  0
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 13 28  2  0
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  7  8  1  0
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 14 15  2  0
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 42 79  1  0
 37 75  1  0
 38 76  1  0
 41 78  1  0
 40 77  1  0
M  END


  Mrv1652306202100433D          

 82 86  0  0  0  0            999 V2000
   -0.4852   -7.9097   -3.0511 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1177   -8.1631   -1.8011 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7973   -7.3173   -0.7702 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1082   -6.2569   -0.8251 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3470   -5.4529    0.3103 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3282   -4.2921    0.1962 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.7450   -3.8124    1.5026 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2926   -2.5203    1.5904 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3861   -1.7400    2.7333 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9864   -2.3135    3.8166 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0323   -1.5498    5.0141 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8547   -0.4477    2.6736 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2549    0.0472    1.4926 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3259    1.3974    1.5295 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3453    2.2501    0.4938 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9382    3.5997    0.6708 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3814    3.9940    1.7420 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9157    4.3507   -0.4742 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3951    5.7189   -0.5054 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.3756    6.7220    0.0474 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.9059    6.7639   -0.7556 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0395    6.0675   -0.3123 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2137    6.0780   -1.0651 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2574    6.7825   -2.2618 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4171    6.7467   -2.9761 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1463    7.4836   -2.7181 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9703    7.4730   -1.9640 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1771   -0.7739    0.3578 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7086   -2.0541    0.4244 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7483   -3.1152   -0.6183 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.6511   -2.8843   -1.8159 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5252   -3.5710   -2.8313 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6488   -1.9484   -1.6883 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.6254   -1.7020   -2.7340 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.0521   -1.0123   -3.9772 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.4282    0.3324   -3.6863 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2292    1.4477   -3.4013 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6466    2.6872   -3.1308 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2617    2.8083   -3.1469 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6500    3.9945   -2.8686 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4514    1.7161   -3.4307 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0335    0.4778   -3.6976 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3394   -5.7360    1.5017 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2427   -6.7967    1.5635 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4618   -7.5723    0.4334 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3553   -8.6055    0.5206 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8528   -8.6514   -3.7668 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6004   -8.0303   -2.9750 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7493   -6.9183   -3.4340 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6446   -6.0284   -1.7424 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2404   -4.6957   -0.2648 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0246   -1.3090    5.3687 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6319   -0.6434    4.8805 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5182   -2.1598    5.7817 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8942    0.2048    3.5414 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7438    1.7054    2.4877 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0782    2.0012   -0.4687 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4979    3.9829   -1.3261 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6435    5.9475   -1.5475 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3187    5.7775    0.0814 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1448    6.4895    1.0945 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8202    7.7251    0.0527 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0099    5.5098    0.6223 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0908    5.5401   -0.7157 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3487    7.3754   -3.7143 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1729    8.0371   -3.6518 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1018    8.0209   -2.3246 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3053   -0.4315   -0.5535 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2649   -3.3100   -0.9902 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7180   -1.3948   -0.8421 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4220   -1.0970   -2.2873 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0605   -2.6657   -3.0223 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3145   -1.6620   -4.4635 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8538   -0.8726   -4.7135 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3133    1.3591   -3.3939 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2853    3.5381   -2.9132 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3410    4.6768   -2.7650 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6292    1.8257   -3.4487 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3943   -0.3743   -3.9206 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1758   -5.1354    2.3946 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7712   -7.0165    2.4862 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3523   -9.0125   -0.3675 H   0  0  0  0  0  0  0  0  0  0  0  0
 15 16  1  0  0  0  0
 29 30  1  0  0  0  0
 16 18  1  0  0  0  0
  5  4  1  0  0  0  0
 18 19  1  0  0  0  0
  8 29  2  0  0  0  0
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  4  3  2  0  0  0  0
 20 21  1  0  0  0  0
  8  9  1  0  0  0  0
 16 17  2  0  0  0  0
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 21 22  2  0  0  0  0
 22 23  1  0  0  0  0
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 23 24  2  0  0  0  0
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 43  5  2  0  0  0  0
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 30  6  1  0  0  0  0
 10 11  1  0  0  0  0
  3  2  1  0  0  0  0
 30 31  1  0  0  0  0
 12 13  1  0  0  0  0
 31 32  2  0  0  0  0
  2  1  1  0  0  0  0
 31 33  1  0  0  0  0
  6  7  1  0  0  0  0
 33 34  1  0  0  0  0
 45 46  1  0  0  0  0
 34 35  1  0  0  0  0
 35 36  1  0  0  0  0
 13 28  2  0  0  0  0
  9 10  1  0  0  0  0
 42 36  1  0  0  0  0
 28 29  1  0  0  0  0
 36 37  2  0  0  0  0
 13 14  1  0  0  0  0
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  7  8  1  0  0  0  0
 38 39  2  0  0  0  0
 14 15  2  0  0  0  0
 39 41  1  0  0  0  0
 41 42  2  0  0  0  0
  6  5  1  0  0  0  0
 39 40  1  0  0  0  0
 30 69  1  6  0  0  0
  6 51  1  6  0  0  0
 12 55  1  0  0  0  0
 28 68  1  0  0  0  0
  4 50  1  0  0  0  0
 44 81  1  0  0  0  0
 43 80  1  0  0  0  0
  1 47  1  0  0  0  0
  1 48  1  0  0  0  0
  1 49  1  0  0  0  0
 46 82  1  0  0  0  0
 14 56  1  0  0  0  0
 15 57  1  0  0  0  0
 18 58  1  0  0  0  0
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 20 61  1  0  0  0  0
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 26 66  1  0  0  0  0
 27 67  1  0  0  0  0
 25 65  1  0  0  0  0
 11 52  1  0  0  0  0
 11 53  1  0  0  0  0
 11 54  1  0  0  0  0
 33 70  1  0  0  0  0
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 34 72  1  0  0  0  0
 35 73  1  0  0  0  0
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 42 79  1  0  0  0  0
 37 75  1  0  0  0  0
 38 76  1  0  0  0  0
 41 78  1  0  0  0  0
 40 77  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0031588

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])N([H])C(=O)C(\[H])=C(/[H])C1=C([H])C2=C(O[C@@]([H])(C3=C([H])C([H])=C(O[H])C(OC([H])([H])[H])=C3[H])[C@]2([H])C(=O)N([H])C([H])([H])C([H])([H])C2=C([H])C([H])=C(O[H])C([H])=C2[H])C(OC([H])([H])[H])=C1[H]

> <INCHI_IDENTIFIER>
InChI=1S/C36H36N2O8/c1-44-30-21-25(8-13-29(30)41)34-33(36(43)38-18-16-23-5-11-27(40)12-6-23)28-19-24(20-31(45-2)35(28)46-34)7-14-32(42)37-17-15-22-3-9-26(39)10-4-22/h3-14,19-21,33-34,39-41H,15-18H2,1-2H3,(H,37,42)(H,38,43)/b14-7+/t33-,34+/m1/s1

> <INCHI_KEY>
DROXVBRNXCRUHP-YRKLVFRVSA-N

> <FORMULA>
C36H36N2O8

> <MOLECULAR_WEIGHT>
624.69

> <EXACT_MASS>
624.247166127

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_ATOM_COUNT>
82

> <JCHEM_AVERAGE_POLARIZABILITY>
66.71284029662544

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2R,3R)-2-(4-hydroxy-3-methoxyphenyl)-N-[2-(4-hydroxyphenyl)ethyl]-5-[(1E)-2-{[2-(4-hydroxyphenyl)ethyl]carbamoyl}eth-1-en-1-yl]-7-methoxy-2,3-dihydro-1-benzofuran-3-carboxamide

> <ALOGPS_LOGP>
4.26

> <JCHEM_LOGP>
4.8148927136666675

> <ALOGPS_LOGS>
-5.85

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.631485870346346

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.125547840622376

> <JCHEM_PKA_STRONGEST_BASIC>
-0.3875367256993837

> <JCHEM_POLAR_SURFACE_AREA>
146.58

> <JCHEM_REFRACTIVITY>
174.24349999999995

> <JCHEM_ROTATABLE_BOND_COUNT>
12

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
8.88e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2R,3R)-2-(4-hydroxy-3-methoxyphenyl)-N-[2-(4-hydroxyphenyl)ethyl]-5-[(1E)-2-{[2-(4-hydroxyphenyl)ethyl]carbamoyl}eth-1-en-1-yl]-7-methoxy-2,3-dihydro-1-benzofuran-3-carboxamide

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 82 86  0  0  0  0  0  0  0  0999 V2000
   -0.4852   -7.9097   -3.0511 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1177   -8.1631   -1.8011 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7973   -7.3173   -0.7702 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1082   -6.2569   -0.8251 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3470   -5.4529    0.3103 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3282   -4.2921    0.1962 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.7450   -3.8124    1.5026 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2926   -2.5203    1.5904 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3861   -1.7400    2.7333 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9864   -2.3135    3.8166 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0323   -1.5498    5.0141 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8547   -0.4477    2.6736 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2549    0.0472    1.4926 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3259    1.3974    1.5295 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3453    2.2501    0.4938 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.3814    3.9940    1.7420 O   0  0  0  0  0  0  0  0  0  0  0  0
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    1.3410    4.6768   -2.7650 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6292    1.8257   -3.4487 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3943   -0.3743   -3.9206 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1758   -5.1354    2.3946 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7712   -7.0165    2.4862 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3523   -9.0125   -0.3675 H   0  0  0  0  0  0  0  0  0  0  0  0
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 29 30  1  0
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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  C   UNK     0      -0.485  -7.910  -3.051  0.00  0.00           C+0
HETATM    2  O   UNK     0      -1.118  -8.163  -1.801  0.00  0.00           O+0
HETATM    3  C   UNK     0      -0.797  -7.317  -0.770  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.108  -6.257  -0.825  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.347  -5.453   0.310  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.328  -4.292   0.196  0.00  0.00           C+0
HETATM    7  O   UNK     0       1.745  -3.812   1.503  0.00  0.00           O+0
HETATM    8  C   UNK     0       1.293  -2.520   1.590  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.386  -1.740   2.733  0.00  0.00           C+0
HETATM   10  O   UNK     0       1.986  -2.313   3.817  0.00  0.00           O+0
HETATM   11  C   UNK     0       2.032  -1.550   5.014  0.00  0.00           C+0
HETATM   12  C   UNK     0       0.855  -0.448   2.674  0.00  0.00           C+0
HETATM   13  C   UNK     0       0.255   0.047   1.493  0.00  0.00           C+0
HETATM   14  C   UNK     0      -0.326   1.397   1.530  0.00  0.00           C+0
HETATM   15  C   UNK     0      -0.345   2.250   0.494  0.00  0.00           C+0
HETATM   16  C   UNK     0      -0.938   3.600   0.671  0.00  0.00           C+0
HETATM   17  O   UNK     0      -1.381   3.994   1.742  0.00  0.00           O+0
HETATM   18  N   UNK     0      -0.916   4.351  -0.474  0.00  0.00           N+0
HETATM   19  C   UNK     0      -1.395   5.719  -0.505  0.00  0.00           C+0
HETATM   20  C   UNK     0      -0.376   6.722   0.047  0.00  0.00           C+0
HETATM   21  C   UNK     0       0.906   6.764  -0.756  0.00  0.00           C+0
HETATM   22  C   UNK     0       2.039   6.067  -0.312  0.00  0.00           C+0
HETATM   23  C   UNK     0       3.214   6.078  -1.065  0.00  0.00           C+0
HETATM   24  C   UNK     0       3.257   6.782  -2.262  0.00  0.00           C+0
HETATM   25  O   UNK     0       4.417   6.747  -2.976  0.00  0.00           O+0
HETATM   26  C   UNK     0       2.146   7.484  -2.718  0.00  0.00           C+0
HETATM   27  C   UNK     0       0.970   7.473  -1.964  0.00  0.00           C+0
HETATM   28  C   UNK     0       0.177  -0.774   0.358  0.00  0.00           C+0
HETATM   29  C   UNK     0       0.709  -2.054   0.424  0.00  0.00           C+0
HETATM   30  C   UNK     0       0.748  -3.115  -0.618  0.00  0.00           C+0
HETATM   31  C   UNK     0       1.651  -2.884  -1.816  0.00  0.00           C+0
HETATM   32  O   UNK     0       1.525  -3.571  -2.831  0.00  0.00           O+0
HETATM   33  N   UNK     0       2.649  -1.948  -1.688  0.00  0.00           N+0
HETATM   34  C   UNK     0       3.625  -1.702  -2.734  0.00  0.00           C+0
HETATM   35  C   UNK     0       3.052  -1.012  -3.977  0.00  0.00           C+0
HETATM   36  C   UNK     0       2.428   0.332  -3.686  0.00  0.00           C+0
HETATM   37  C   UNK     0       3.229   1.448  -3.401  0.00  0.00           C+0
HETATM   38  C   UNK     0       2.647   2.687  -3.131  0.00  0.00           C+0
HETATM   39  C   UNK     0       1.262   2.808  -3.147  0.00  0.00           C+0
HETATM   40  O   UNK     0       0.650   3.994  -2.869  0.00  0.00           O+0
HETATM   41  C   UNK     0       0.451   1.716  -3.431  0.00  0.00           C+0
HETATM   42  C   UNK     0       1.034   0.478  -3.698  0.00  0.00           C+0
HETATM   43  C   UNK     0      -0.339  -5.736   1.502  0.00  0.00           C+0
HETATM   44  C   UNK     0      -1.243  -6.797   1.563  0.00  0.00           C+0
HETATM   45  C   UNK     0      -1.462  -7.572   0.433  0.00  0.00           C+0
HETATM   46  O   UNK     0      -2.355  -8.605   0.521  0.00  0.00           O+0
HETATM   47  H   UNK     0      -0.853  -8.651  -3.767  0.00  0.00           H+0
HETATM   48  H   UNK     0       0.600  -8.030  -2.975  0.00  0.00           H+0
HETATM   49  H   UNK     0      -0.749  -6.918  -3.434  0.00  0.00           H+0
HETATM   50  H   UNK     0       0.645  -6.028  -1.742  0.00  0.00           H+0
HETATM   51  H   UNK     0       2.240  -4.696  -0.265  0.00  0.00           H+0
HETATM   52  H   UNK     0       1.025  -1.309   5.369  0.00  0.00           H+0
HETATM   53  H   UNK     0       2.632  -0.643   4.880  0.00  0.00           H+0
HETATM   54  H   UNK     0       2.518  -2.160   5.782  0.00  0.00           H+0
HETATM   55  H   UNK     0       0.894   0.205   3.541  0.00  0.00           H+0
HETATM   56  H   UNK     0      -0.744   1.705   2.488  0.00  0.00           H+0
HETATM   57  H   UNK     0       0.078   2.001  -0.469  0.00  0.00           H+0
HETATM   58  H   UNK     0      -0.498   3.983  -1.326  0.00  0.00           H+0
HETATM   59  H   UNK     0      -1.644   5.947  -1.548  0.00  0.00           H+0
HETATM   60  H   UNK     0      -2.319   5.777   0.081  0.00  0.00           H+0
HETATM   61  H   UNK     0      -0.145   6.489   1.095  0.00  0.00           H+0
HETATM   62  H   UNK     0      -0.820   7.725   0.053  0.00  0.00           H+0
HETATM   63  H   UNK     0       2.010   5.510   0.622  0.00  0.00           H+0
HETATM   64  H   UNK     0       4.091   5.540  -0.716  0.00  0.00           H+0
HETATM   65  H   UNK     0       4.349   7.375  -3.714  0.00  0.00           H+0
HETATM   66  H   UNK     0       2.173   8.037  -3.652  0.00  0.00           H+0
HETATM   67  H   UNK     0       0.102   8.021  -2.325  0.00  0.00           H+0
HETATM   68  H   UNK     0      -0.305  -0.432  -0.554  0.00  0.00           H+0
HETATM   69  H   UNK     0      -0.265  -3.310  -0.990  0.00  0.00           H+0
HETATM   70  H   UNK     0       2.718  -1.395  -0.842  0.00  0.00           H+0
HETATM   71  H   UNK     0       4.422  -1.097  -2.287  0.00  0.00           H+0
HETATM   72  H   UNK     0       4.061  -2.666  -3.022  0.00  0.00           H+0
HETATM   73  H   UNK     0       2.314  -1.662  -4.463  0.00  0.00           H+0
HETATM   74  H   UNK     0       3.854  -0.873  -4.713  0.00  0.00           H+0
HETATM   75  H   UNK     0       4.313   1.359  -3.394  0.00  0.00           H+0
HETATM   76  H   UNK     0       3.285   3.538  -2.913  0.00  0.00           H+0
HETATM   77  H   UNK     0       1.341   4.677  -2.765  0.00  0.00           H+0
HETATM   78  H   UNK     0      -0.629   1.826  -3.449  0.00  0.00           H+0
HETATM   79  H   UNK     0       0.394  -0.374  -3.921  0.00  0.00           H+0
HETATM   80  H   UNK     0      -0.176  -5.135   2.395  0.00  0.00           H+0
HETATM   81  H   UNK     0      -1.771  -7.016   2.486  0.00  0.00           H+0
HETATM   82  H   UNK     0      -2.352  -9.012  -0.368  0.00  0.00           H+0
CONECT    1    2   47   48   49                                             
CONECT    2    3    1                                                       
CONECT    3    4   45    2                                                  
CONECT    4    5    3   50                                                  
CONECT    5    4   43    6                                                  
CONECT    6   30    7    5   51                                             
CONECT    7    6    8                                                       
CONECT    8   29    9    7                                                  
CONECT    9    8   12   10                                                  
CONECT   10   11    9                                                       
CONECT   11   10   52   53   54                                             
CONECT   12    9   13   55                                                  
CONECT   13   12   28   14                                                  
CONECT   14   13   15   56                                                  
CONECT   15   16   14   57                                                  
CONECT   16   15   18   17                                                  
CONECT   17   16                                                            
CONECT   18   16   19   58                                                  
CONECT   19   18   20   59   60                                             
CONECT   20   19   21   61   62                                             
CONECT   21   20   22   27                                                  
CONECT   22   21   23   63                                                  
CONECT   23   22   24   64                                                  
CONECT   24   23   26   25                                                  
CONECT   25   24   65                                                       
CONECT   26   24   27   66                                                  
CONECT   27   26   21   67                                                  
CONECT   28   13   29   68                                                  
CONECT   29   30    8   28                                                  
CONECT   30   29    6   31   69                                             
CONECT   31   30   32   33                                                  
CONECT   32   31                                                            
CONECT   33   31   34   70                                                  
CONECT   34   33   35   71   72                                             
CONECT   35   34   36   73   74                                             
CONECT   36   35   42   37                                                  
CONECT   37   36   38   75                                                  
CONECT   38   37   39   76                                                  
CONECT   39   38   41   40                                                  
CONECT   40   39   77                                                       
CONECT   41   39   42   78                                                  
CONECT   42   36   41   79                                                  
CONECT   43   44    5   80                                                  
CONECT   44   45   43   81                                                  
CONECT   45    3   44   46                                                  
CONECT   46   45   82                                                       
CONECT   47    1                                                            
CONECT   48    1                                                            
CONECT   49    1                                                            
CONECT   50    4                                                            
CONECT   51    6                                                            
CONECT   52   11                                                            
CONECT   53   11                                                            
CONECT   54   11                                                            
CONECT   55   12                                                            
CONECT   56   14                                                            
CONECT   57   15                                                            
CONECT   58   18                                                            
CONECT   59   19                                                            
CONECT   60   19                                                            
CONECT   61   20                                                            
CONECT   62   20                                                            
CONECT   63   22                                                            
CONECT   64   23                                                            
CONECT   65   25                                                            
CONECT   66   26                                                            
CONECT   67   27                                                            
CONECT   68   28                                                            
CONECT   69   30                                                            
CONECT   70   33                                                            
CONECT   71   34                                                            
CONECT   72   34                                                            
CONECT   73   35                                                            
CONECT   74   35                                                            
CONECT   75   37                                                            
CONECT   76   38                                                            
CONECT   77   40                                                            
CONECT   78   41                                                            
CONECT   79   42                                                            
CONECT   80   43                                                            
CONECT   81   44                                                            
CONECT   82   46                                                            
MASTER        0    0    0    0    0    0    0    0   82    0  172    0
END

RDKit          3D

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M  END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₃₆H₃₆N₂O₈

Average Mass

624.6900 Da

Monoisotopic Mass

624.24717 Da

IUPAC Name

(2R,3R)-2-(4-hydroxy-3-methoxyphenyl)-N-[2-(4-hydroxyphenyl)ethyl]-5-[(1E)-2-{[2-(4-hydroxyphenyl)ethyl]carbamoyl}eth-1-en-1-yl]-7-methoxy-2,3-dihydro-1-benzofuran-3-carboxamide

Traditional Name

(2R,3R)-2-(4-hydroxy-3-methoxyphenyl)-N-[2-(4-hydroxyphenyl)ethyl]-5-[(1E)-2-{[2-(4-hydroxyphenyl)ethyl]carbamoyl}eth-1-en-1-yl]-7-methoxy-2,3-dihydro-1-benzofuran-3-carboxamide

CAS Registry Number

Not Available

SMILES

[H]OC1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])N([H])C(=O)C(\[H])=C(/[H])C1=C([H])C(OC([H])([H])[H])=C2O[C@@]([H])(C3=C([H])C(OC([H])([H])[H])=C(O[H])C([H])=C3[H])[C@]([H])(C(=O)N([H])C([H])([H])C([H])([H])C3=C([H])C([H])=C(O[H])C([H])=C3[H])C2=C1[H]

InChI Identifier

InChI=1S/C36H36N2O8/c1-44-30-21-25(8-13-29(30)41)34-33(36(43)38-18-16-23-5-11-27(40)12-6-23)28-19-24(20-31(45-2)35(28)46-34)7-14-32(42)37-17-15-22-3-9-26(39)10-4-22/h3-14,19-21,33-34,39-41H,15-18H2,1-2H3,(H,37,42)(H,38,43)/b14-7+/t33-,34+/m1/s1

InChI Key

DROXVBRNXCRUHP-YRKLVFRVSA-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
Cannabis sativa	Plant	KNApSAcK
Capsicum annuum var.grossum	Plant	KNApSAcK
Hibiscus cannabinus	LOTUS Database	35616633
Hyoscyamus niger	Plant	KNApSAcK
Nicotiana tabacum	Plant	KNApSAcK
Solanum tuberosum	JEOL database	King, R. R., et al, Phytochemistry 66, 2468 (2005)
Xylopia aethiopica	Plant	KNApSAcK

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
Neolignan skeleton
Cinnamic acid amide
Cinnamic acid or derivatives
Methoxyphenol
Benzofuran
Coumaran
Anisole
Phenoxy compound
Phenol ether
Methoxybenzene
Styrene
Alkyl aryl ether
1-hydroxy-2-unsubstituted benzenoid
Phenol
Benzenoid
Monocyclic benzene moiety
Secondary carboxylic acid amide
Carboxamide group
Oxacycle
Organoheterocyclic compound
Ether
Carboxylic acid derivative
Organooxygen compound
Organic oxygen compound
Organopnictogen compound
Organic oxide
Carbonyl group
Organic nitrogen compound
Hydrocarbon derivative
Organonitrogen 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	4.26	ALOGPS
logP	4.81	ChemAxon
logS	-5.8	ALOGPS
pKa (Strongest Acidic)	9.13	ChemAxon
pKa (Strongest Basic)	-0.39	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	146.58 Å²	ChemAxon
Rotatable Bond Count	12	ChemAxon
Refractivity	174.24 m³·mol⁻¹	ChemAxon
Polarizability	66.71 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

4944913

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

6440658

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Nchiozem-Ngnitedem VA, Omosa LK, Bedane KG, Derese S, Brieger L, Strohmann C, Spiteller M: Anti-inflammatory steroidal sapogenins and a conjugated chalcone-stilbene from Dracaena usambarensis Engl. Fitoterapia. 2020 Oct;146:104717. doi: 10.1016/j.fitote.2020.104717. Epub 2020 Aug 31. [PubMed:32877711 ]
Pap N, Hamberg L, Pihlava JM, Hellstrom J, Mattila P, Eurola M, Pihlanto A: Impact of enzymatic hydrolysis on the nutrients, phytochemicals and sensory properties of oil hemp seed cake (Cannabis sativa L. FINOLA variety). Food Chem. 2020 Aug 1;320:126530. doi: 10.1016/j.foodchem.2020.126530. Epub 2020 Mar 5. [PubMed:32222655 ]
Nagumo M, Ninomiya M, Oshima N, Itoh T, Tanaka K, Nishina A, Koketsu M: Comparative analysis of stilbene and benzofuran neolignan derivatives as acetylcholinesterase inhibitors with neuroprotective and anti-inflammatory activities. Bioorg Med Chem Lett. 2019 Sep 1;29(17):2475-2479. doi: 10.1016/j.bmcl.2019.07.026. Epub 2019 Jul 18. [PubMed:31350127 ]
Wang ZW, Li Y, Liu DH, Mu Y, Dong HJ, Zhou HL, Guo LP, Wang X: Four new phenolic constituents from the rhizomes of Gastrodia elata Blume. Nat Prod Res. 2019 Apr;33(8):1140-1146. doi: 10.1080/14786419.2018.1460836. Epub 2018 Apr 20. [PubMed:29676594 ]
Luo Q, Yan X, Bobrovskaya L, Ji M, Yuan H, Lou H, Fan P: Anti-neuroinflammatory effects of grossamide from hemp seed via suppression of TLR-4-mediated NF-kappaB signaling pathways in lipopolysaccharide-stimulated BV2 microglia cells. Mol Cell Biochem. 2017 Apr;428(1-2):129-137. doi: 10.1007/s11010-016-2923-7. Epub 2017 Feb 21. [PubMed:28224333 ]
King, R. R., et al. (2005). King, R. R., et al, Phytochemistry 66, 2468 (2005). Phytochem..

Showing NP-Card for N-trans-grossamide (NP0031588)

MOL for NP0031588 (N-trans-grossamide)

3D MOL for NP0031588 (N-trans-grossamide)

3D SDF for NP0031588 (N-trans-grossamide)

3D-SDF for NP0031588 (N-trans-grossamide)

PDB for NP0031588 (N-trans-grossamide)

3D PDB for NP0031588 (N-trans-grossamide)

SMILES for NP0031588 (N-trans-grossamide)

INCHI for NP0031588 (N-trans-grossamide)

Structure for NP0031588 (N-trans-grossamide)

3D Structure for NP0031588 (N-trans-grossamide)