NP-MRD: Showing NP-Card for Acetovaltrate (NP0057621)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-04-28 03:01:44 UTC

Updated at

2022-04-28 03:01:44 UTC

NP-MRD ID

NP0057621

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Acetovaltrate

Description

Acevaltrate, also known as acevaltric acid, belongs to the class of organic compounds known as tetracarboxylic acids and derivatives. These are carboxylic acids containing exactly four carboxyl groups. Acetovaltrate is found in Centranthus macrosiphon, Centranthus ruber , Valeriana jatamansi , Valeriana microphylla, Valeriana officinalis , Valeriana prionophylla, Valeriana sitchensis, Valeriana spp and Valeriana spp.. Acetovaltrate was first documented in 2017 (PMID: 29232391). Based on a literature review a small amount of articles have been published on Acevaltrate (PMID: 35363851) (PMID: 33662720) (PMID: 33627137) (PMID: 33184448).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304282205012D          

 34 36  0  0  1  0            999 V2000
   -0.7145    4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    4.5375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    3.7125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0000    3.3000    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7145    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3276    3.1605    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9920    2.4068    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.1715    2.4930    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.6131    2.2381    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    1.6861    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4045    1.6923    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2295    1.6923    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6420    2.4068    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6420    0.9779    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4670    0.9779    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4670    0.1529    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4670    1.8029    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2920    0.9779    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7045    0.2634    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5295    0.2634    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2920   -0.4511    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    3.3000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8769    1.8619    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    5.7750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579    5.7750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    7.0125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  6  0  0  0
  1  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  5  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
  9 11  1  6  0  0  0
  8 12  1  1  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 13 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 16 18  1  0  0  0  0
 16 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 20 22  1  0  0  0  0
  4 23  1  1  0  0  0
 23 24  1  0  0  0  0
 24 25  2  0  0  0  0
 24 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 27 29  1  0  0  0  0
  1 30  1  0  0  0  0
 30 31  1  0  0  0  0
 31 32  1  0  0  0  0
 32 33  2  0  0  0  0
 32 34  1  0  0  0  0
M  END

     RDKit          3D

 66 68  0  0  0  0  0  0  0  0999 V2000
   -0.9341    5.5655    1.3735 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3769    5.1774    0.8189 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3355    4.9604    1.5921 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5778    5.0455   -0.5404 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8797    4.6645   -1.0040 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2530    3.3283   -0.4315 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3293    3.1762    0.3360 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6918    1.9545    0.8740 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2331    0.7836    0.1772 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.6657   -0.3838    0.8487 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5529   -1.3148    0.2963 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9599   -1.0550   -0.8649 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9778   -2.5284    1.0461 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2493   -3.7640    0.5615 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.5706   -3.9429   -0.9064 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7193   -5.0070    1.2797 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7580    0.8959    0.0579 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4425    2.1507   -0.7005 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4455    1.9742   -1.5174 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0868    0.5658   -1.4510 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.2054    0.4982   -0.5870 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4504    0.0427   -0.9662 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6125   -0.3323   -2.1422 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5480    0.0169    0.0410 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8409   -0.4699   -0.5627 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.7125   -1.8782   -1.1284 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2993    0.4765   -1.6643 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8902   -0.5004    0.3814 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8962   -1.2507    1.5326 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0729   -1.2059    2.4748 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9089   -1.9789    1.7955 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0960   -0.1468   -0.8032 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.9141   -1.5208   -0.4137 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8041   -1.0977   -1.4831 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8327    5.7882    2.4628 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6856    4.7559    1.1981 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3681    6.4695    0.8807 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6439    5.4019   -0.7056 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9079    4.6006   -2.1071 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9204    4.0575    0.5269 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7074    0.8022   -0.8082 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0776   -2.6743    1.0254 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6965   -2.3851    2.1079 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1508   -3.6391    0.6318 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6660   -3.7269   -1.0286 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9432   -3.3071   -1.5517 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4463   -5.0238   -1.1244 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6749   -5.3580    0.8409 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9842   -5.8219    1.1012 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9000   -4.8275    2.3587 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2392    0.9931    1.0322 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0156    2.6922   -2.1997 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3271    0.1954   -2.4544 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7378    0.9948    0.4966 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2558   -0.6707    0.8586 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8448   -2.4065   -0.6775 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6338   -2.4664   -0.9295 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5681   -1.7579   -2.2295 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4006    0.3786   -1.8349 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1423    1.5175   -1.2655 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8032    0.3104   -2.6209 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9228   -0.6877    1.9894 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8221   -0.7407    3.4311 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3961   -2.2703    2.5982 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0195   -2.0799   -0.7692 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4044   -2.0129    0.4461 H   0  0  0  0  0  0  0  0  0  0  0  0
 15 14  1  0
 14 16  1  0
 14 13  1  0
 13 11  1  0
 11 12  2  0
 11 10  1  0
 10  9  1  0
  9  8  1  0
  8  7  1  0
  7  6  2  0
  6  5  1  0
  5  4  1  0
  4  2  1  0
  2  1  1  0
  2  3  2  0
  6 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  2  0
 22 24  1  0
 24 25  1  0
 25 26  1  0
 25 27  1  0
 25 28  1  1
 28 29  1  0
 29 30  1  0
 29 31  2  0
 20 32  1  0
 32 33  1  0
 33 34  1  0
 32 17  1  0
 17  9  1  0
 17 18  1  0
 32 34  1  6
 15 45  1  0
 15 46  1  0
 15 47  1  0
 14 44  1  6
 16 48  1  0
 16 49  1  0
 16 50  1  0
 13 42  1  0
 13 43  1  0
  9 41  1  6
  7 40  1  0
  5 38  1  0
  5 39  1  0
  1 35  1  0
  1 36  1  0
  1 37  1  0
 19 52  1  0
 20 53  1  6
 24 54  1  0
 24 55  1  0
 26 56  1  0
 26 57  1  0
 26 58  1  0
 27 59  1  0
 27 60  1  0
 27 61  1  0
 30 62  1  0
 30 63  1  0
 30 64  1  0
 33 65  1  0
 33 66  1  0
 17 51  1  1
M  END


  Mrv1652304282205012D          

 34 36  0  0  1  0            999 V2000
   -0.7145    4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    4.5375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    3.7125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0000    3.3000    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7145    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3276    3.1605    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9920    2.4068    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.1715    2.4930    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.6131    2.2381    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    1.6861    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4045    1.6923    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2295    1.6923    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6420    2.4068    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6420    0.9779    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4670    0.9779    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4670    0.1529    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4670    1.8029    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2920    0.9779    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7045    0.2634    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5295    0.2634    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2920   -0.4511    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    3.3000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8769    1.8619    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    5.7750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579    5.7750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    7.0125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  6  0  0  0
  1  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  5  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
  9 11  1  6  0  0  0
  8 12  1  1  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 13 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 16 18  1  0  0  0  0
 16 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 20 22  1  0  0  0  0
  4 23  1  1  0  0  0
 23 24  1  0  0  0  0
 24 25  2  0  0  0  0
 24 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 27 29  1  0  0  0  0
  1 30  1  0  0  0  0
 30 31  1  0  0  0  0
 31 32  1  0  0  0  0
 32 33  2  0  0  0  0
 32 34  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0057621

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)CC(=O)O[C@@H]1OC=C(COC(C)=O)C2=C[C@H](OC(=O)CC(C)(C)OC(C)=O)[C@]3(CO3)[C@@H]12

> <INCHI_IDENTIFIER>
InChI=1S/C24H32O10/c1-13(2)7-19(27)33-22-21-17(16(11-30-22)10-29-14(3)25)8-18(24(21)12-31-24)32-20(28)9-23(5,6)34-15(4)26/h8,11,13,18,21-22H,7,9-10,12H2,1-6H3/t18-,21+,22-,24+/m0/s1

> <INCHI_KEY>
FWKBQAVMKVZEOT-STCFVSJZSA-N

> <FORMULA>
C24H32O10

> <MOLECULAR_WEIGHT>
480.51

> <EXACT_MASS>
480.19954723

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
66

> <JCHEM_AVERAGE_POLARIZABILITY>
48.82492047668765

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1S,6S,7R,7aS)-4-[(acetyloxy)methyl]-1-[(3-methylbutanoyl)oxy]-6,7a-dihydro-1H-spiro[cyclopenta[c]pyran-7,2'-oxirane]-6-yl 3-(acetyloxy)-3-methylbutanoate

> <ALOGPS_LOGP>
2.71

> <JCHEM_LOGP>
1.3624416396666672

> <ALOGPS_LOGS>
-4.39

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
18.236658166565398

> <JCHEM_PKA_STRONGEST_BASIC>
-4.145194191479699

> <JCHEM_POLAR_SURFACE_AREA>
126.96000000000004

> <JCHEM_REFRACTIVITY>
116.08749999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
13

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.97e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1S,6S,7R,7aS)-4-[(acetyloxy)methyl]-1-[(3-methylbutanoyl)oxy]-6,7a-dihydro-1H-spiro[cyclopenta[c]pyran-7,2'-oxirane]-6-yl 3-(acetyloxy)-3-methylbutanoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 28-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   28-APR-22         0                                  
HETATM    1  C   UNK     0      -1.334   8.470   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.000   9.240   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       1.334   8.470   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0       1.334   6.930   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.000   6.160   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -1.334   6.930   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -2.478   5.900   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -1.852   4.493   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -0.320   4.654   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.144   4.178   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       0.000   3.147   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0      -2.622   3.159   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0      -4.162   3.159   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0      -4.932   4.493   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0      -4.932   1.825   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -6.472   1.825   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -6.472   0.285   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -6.472   3.365   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      -8.012   1.825   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0      -8.782   0.492   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0     -10.322   0.492   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0      -8.012  -0.842   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       2.667   6.160   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0       2.667   4.620   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       1.637   3.476   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0       4.001   3.850   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       5.335   4.620   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       5.335   6.160   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       6.668   3.850   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      -2.667   9.240   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0      -2.667  10.780   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0      -4.001  11.550   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0      -5.335  10.780   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0      -4.001  13.090   0.000  0.00  0.00           C+0
CONECT    1    2    6   30                                                  
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5   23                                                  
CONECT    5    4    6    9                                                  
CONECT    6    5    1    7                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   12                                                  
CONECT    9    8    5   10   11                                             
CONECT   10    9   11                                                       
CONECT   11   10    9                                                       
CONECT   12    8   13                                                       
CONECT   13   12   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13   16                                                       
CONECT   16   15   17   18   19                                             
CONECT   17   16                                                            
CONECT   18   16                                                            
CONECT   19   16   20                                                       
CONECT   20   19   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20                                                            
CONECT   23    4   24                                                       
CONECT   24   23   25   26                                                  
CONECT   25   24                                                            
CONECT   26   24   27                                                       
CONECT   27   26   28   29                                                  
CONECT   28   27                                                            
CONECT   29   27                                                            
CONECT   30    1   31                                                       
CONECT   31   30   32                                                       
CONECT   32   31   33   34                                                  
CONECT   33   32                                                            
CONECT   34   32                                                            
MASTER        0    0    0    0    0    0    0    0   34    0   72    0
END

View in JSmol

Synonyms

Value	Source
Acevaltric acid	Generator

Chemical Formula

C₂₄H₃₂O₁₀

Average Mass

480.5100 Da

Monoisotopic Mass

480.19955 Da

IUPAC Name

(1S,6S,7R,7aS)-4-[(acetyloxy)methyl]-1-[(3-methylbutanoyl)oxy]-6,7a-dihydro-1H-spiro[cyclopenta[c]pyran-7,2'-oxirane]-6-yl 3-(acetyloxy)-3-methylbutanoate

Traditional Name

(1S,6S,7R,7aS)-4-[(acetyloxy)methyl]-1-[(3-methylbutanoyl)oxy]-6,7a-dihydro-1H-spiro[cyclopenta[c]pyran-7,2'-oxirane]-6-yl 3-(acetyloxy)-3-methylbutanoate

CAS Registry Number

Not Available

SMILES

CC(C)CC(=O)O[C@@H]1OC=C(COC(C)=O)C2=C[C@H](OC(=O)CC(C)(C)OC(C)=O)[C@]3(CO3)[C@@H]12

InChI Identifier

InChI=1S/C24H32O10/c1-13(2)7-19(27)33-22-21-17(16(11-30-22)10-29-14(3)25)8-18(24(21)12-31-24)32-20(28)9-23(5,6)34-15(4)26/h8,11,13,18,21-22H,7,9-10,12H2,1-6H3/t18-,21+,22-,24+/m0/s1

InChI Key

FWKBQAVMKVZEOT-STCFVSJZSA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Centranthus macrosiphon	LOTUS Database	35616633
Centranthus ruber	Plant	KNApSAcK
Valeriana jatamansi	Plant	KNApSAcK
Valeriana microphylla	LOTUS Database	35616633
Valeriana officinalis	Plant	KNApSAcK
Valeriana prionophylla	LOTUS Database	35616633
Valeriana sitchensis	LOTUS Database	35616633
Valeriana spp	Plant	KNApSAcK
Valeriana spp.	Plant	KNApSAcK

Chemical Taxonomy

Description

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

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Tetracarboxylic acids and derivatives

Direct Parent

Tetracarboxylic acids and derivatives

Alternative Parents

Substituents

Tetracarboxylic acid or derivatives
Iridoid-skeleton
Bicyclic monoterpenoid
Monoterpenoid
Fatty acid ester
Fatty acyl
Carboxylic acid ester
Oxacycle
Ether
Oxirane
Dialkyl ether
Acetal
Organoheterocyclic compound
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Carbonyl group
Organic oxygen compound
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

fatty acid ester (CHEBI:80704 )

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	2.71	ALOGPS
logP	1.36	ChemAxon
logS	-4.4	ALOGPS
pKa (Strongest Acidic)	18.24	ChemAxon
pKa (Strongest Basic)	-4.1	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	126.96 Å²	ChemAxon
Rotatable Bond Count	13	ChemAxon
Refractivity	116.09 m³·mol⁻¹	ChemAxon
Polarizability	48.82 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00010724

Chemspider ID

59141

KEGG Compound ID

C16752

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Acevaltrate

METLIN ID

Not Available

PubChem Compound

65717

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

rw1522191

References

General References

Sharma S, Parasher K, Mukherjee P, Sharma YP: Cryopreservation of a threatened medicinal plant, Valeriana jatamansi Jones, using vitrification and assessment of biosynthetic stability of regenerants. Cryo Letters. 2021 Sep-Oct;42(5):300-308. [PubMed:35363851 ]
Wang X, Tan Z, Chen S, Gui L, Li X, Ke D, Hou L, Leung JYS: Norethindrone causes cellular and hepatic injury in zebrafish by compromising the metabolic processes associated with antioxidant defence: Insights from metabolomics. Chemosphere. 2021 Jul;275:130049. doi: 10.1016/j.chemosphere.2021.130049. Epub 2021 Feb 22. [PubMed:33662720 ]
Sun T, Xu Y, Xu Z, Cao B, Zhang Z, Wang Q, Kong Y, Mao X: Inhibition of the Otub1/c-Maf axis by the herbal acevaltrate induces myeloma cell apoptosis. Cell Commun Signal. 2021 Feb 24;19(1):24. doi: 10.1186/s12964-020-00676-w. [PubMed:33627137 ]
Sun T, Xu YJ, Jiang SY, Xu Z, Cao BY, Sethi G, Zeng YY, Kong Y, Mao XL: Suppression of the USP10/CCND1 axis induces glioblastoma cell apoptosis. Acta Pharmacol Sin. 2021 Aug;42(8):1338-1346. doi: 10.1038/s41401-020-00551-x. Epub 2020 Nov 12. [PubMed:33184448 ]
Wang F, Zhang Y, Wu S, He Y, Dai Z, Ma S, Liu B: Studies of the structure-antioxidant activity relationships and antioxidant activity mechanism of iridoid valepotriates and their degradation products. PLoS One. 2017 Dec 12;12(12):e0189198. doi: 10.1371/journal.pone.0189198. eCollection 2017. [PubMed:29232391 ]

Showing NP-Card for Acetovaltrate (NP0057621)

MOL for NP0057621 (Acetovaltrate)

3D MOL for NP0057621 (Acetovaltrate)

3D SDF for NP0057621 (Acetovaltrate)

3D-SDF for NP0057621 (Acetovaltrate)

PDB for NP0057621 (Acetovaltrate)

3D PDB for NP0057621 (Acetovaltrate)

SMILES for NP0057621 (Acetovaltrate)

INCHI for NP0057621 (Acetovaltrate)

Structure for NP0057621 (Acetovaltrate)

3D Structure for NP0057621 (Acetovaltrate)