NP-MRD: Showing NP-Card for (1r,2r,4ar,5r,7s,8as)-7-(acetyloxy)-1-[(1e)-2-(2-hydroxy-5-oxo-2h-furan-3-yl)ethenyl]-5-(methoxycarbonyl)-1,4a-dimethyl-8-oxo-hexahydro-2h-naphthalene-2-carboxylic acid (NP0152072)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-09-02 08:29:11 UTC

Updated at

2022-09-02 08:29:12 UTC

NP-MRD ID

NP0152072

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1r,2r,4ar,5r,7s,8as)-7-(acetyloxy)-1-[(1e)-2-(2-hydroxy-5-oxo-2h-furan-3-yl)ethenyl]-5-(methoxycarbonyl)-1,4a-dimethyl-8-oxo-hexahydro-2h-naphthalene-2-carboxylic acid

Description

Salvidivin C belongs to the class of organic compounds known as diterpene lactones. These are diterpenoids containing a lactone moiety. (1r,2r,4ar,5r,7s,8as)-7-(acetyloxy)-1-[(1e)-2-(2-hydroxy-5-oxo-2h-furan-3-yl)ethenyl]-5-(methoxycarbonyl)-1,4a-dimethyl-8-oxo-hexahydro-2h-naphthalene-2-carboxylic acid is found in Salvia divinorum. Based on a literature review very few articles have been published on Salvidivin C.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309022210292D          

 33 35  0  0  1  0            999 V2000
    0.7145   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -2.8875    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
    2.1434   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.3276    0.6320    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3882    0.6320    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1060    1.4072    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6363    2.0392    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4367    2.8397    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1364    3.2769    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1939    4.0999    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7684    2.7466    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4593    1.9817    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8965    1.2820    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.2868   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 C   0  0  1  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
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  5  3  1  6  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  6  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  9 11  2  0  0  0  0
  7 12  1  0  0  0  0
 12 13  2  0  0  0  0
 14 12  1  6  0  0  0
 14 15  1  0  0  0  0
 15 16  1  6  0  0  0
 15 17  1  1  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 20 21  1  0  0  0  0
 21 22  2  0  0  0  0
 21 23  1  0  0  0  0
 23 24  1  0  0  0  0
 19 24  1  0  0  0  0
 24 25  1  0  0  0  0
 15 26  1  0  0  0  0
 26 27  1  6  0  0  0
 27 28  2  0  0  0  0
 27 29  1  0  0  0  0
 26 30  1  0  0  0  0
 30 31  1  0  0  0  0
 31 32  1  0  0  0  0
 14 32  1  0  0  0  0
  5 32  1  0  0  0  0
 32 33  1  6  0  0  0
M  END

     RDKit          3D

 61 63  0  0  0  0  0  0  0  0999 V2000
   -5.6488   -2.9725    0.0246 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6022   -2.0837    0.3262 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4913   -1.9165   -0.5083 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5213   -2.6304   -1.5383 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4498   -0.9845   -0.1282 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.9488    0.4404    0.0258 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9434    1.1263    0.9461 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.9587    2.5269    0.7147 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6989    3.3628    1.5259 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6827    4.8204    1.2975 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3800    2.8573    2.4594 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6133    0.5398    0.9572 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1667    0.8885    1.8047 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1269   -0.4714   -0.0126 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.1804   -0.2062   -0.5934 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.1793    1.1278   -1.3953 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2428   -0.0619    0.3662 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1004    0.0448    1.1404 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1587    0.1771    2.0957 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8406   -0.9142    2.5892 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8416   -0.4798    3.5144 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6851   -1.1737    4.1819 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7530    0.9017    3.5784 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6817    1.3426    2.8088 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.1241    2.2629    1.8585 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5937   -1.3237   -1.5535 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.7172   -0.9291   -2.4269 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8991   -1.2327   -2.1636 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5234   -0.1924   -3.6006 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5285   -1.9608   -2.3180 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7964   -2.1598   -1.6337 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2156   -0.9016   -0.9715 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.5234    0.0962   -2.0695 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4548   -3.6851   -0.7737 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8000   -3.5897    0.9593 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6079   -2.4512   -0.1714 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0732   -1.2544    0.9292 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9103    0.3818    0.5768 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1383    1.0048   -0.8687 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4224    0.9784    1.9655 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7895    5.3404    1.6922 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5767    5.3029    1.8062 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7850    5.1099    0.2195 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0020   -1.4062    0.6443 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6003    1.8287   -0.8186 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2385    1.4882   -1.4372 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8745    1.0160   -2.4130 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3098   -1.4741    0.5770 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9106    1.4503    1.0306 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6075   -1.9084    2.2855 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9019    1.8146    3.4708 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2659    1.8501    0.9743 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0297   -2.1341   -0.8813 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1583   -0.6142   -4.4387 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4310   -1.4833   -3.3069 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8828   -3.0103   -2.5836 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7315   -3.0534   -1.0272 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5329   -2.3351   -2.4807 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4082    1.1265   -1.8112 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6011   -0.0749   -2.3839 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9918   -0.1387   -3.0375 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  3  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
  9 11  2  0
  7 12  1  0
 12 13  2  0
 12 14  1  0
 14 32  1  0
 32 33  1  6
 32 31  1  0
 31 30  1  0
 30 26  1  0
 26 27  1  0
 27 29  1  0
 27 28  2  0
 26 15  1  0
 15 16  1  0
 15 17  1  1
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 21 23  1  0
 23 24  1  0
 24 25  1  0
 32  5  1  0
 24 19  1  0
 15 14  1  0
  1 34  1  0
  1 35  1  0
  1 36  1  0
  5 37  1  1
  6 38  1  0
  6 39  1  0
  7 40  1  1
 10 41  1  0
 10 42  1  0
 10 43  1  0
 14 44  1  1
 33 59  1  0
 33 60  1  0
 33 61  1  0
 31 57  1  0
 31 58  1  0
 30 55  1  0
 30 56  1  0
 26 53  1  1
 29 54  1  0
 16 45  1  0
 16 46  1  0
 16 47  1  0
 17 48  1  0
 18 49  1  0
 20 50  1  0
 24 51  1  1
 25 52  1  0
M  END


  Mrv1652309022210292D          

 33 35  0  0  1  0            999 V2000
    0.7145   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -2.8875    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
    2.1434   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.3276    0.6320    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3882    0.6320    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1060    1.4072    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6363    2.0392    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4367    2.8397    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1364    3.2769    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1939    4.0999    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7684    2.7466    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4593    1.9817    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8965    1.2820    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.2868   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 C   0  0  1  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
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  5  3  1  6  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  6  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  9 11  2  0  0  0  0
  7 12  1  0  0  0  0
 12 13  2  0  0  0  0
 14 12  1  6  0  0  0
 14 15  1  0  0  0  0
 15 16  1  6  0  0  0
 15 17  1  1  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 20 21  1  0  0  0  0
 21 22  2  0  0  0  0
 21 23  1  0  0  0  0
 23 24  1  0  0  0  0
 19 24  1  0  0  0  0
 24 25  1  0  0  0  0
 15 26  1  0  0  0  0
 26 27  1  6  0  0  0
 27 28  2  0  0  0  0
 27 29  1  0  0  0  0
 26 30  1  0  0  0  0
 30 31  1  0  0  0  0
 31 32  1  0  0  0  0
 14 32  1  0  0  0  0
  5 32  1  0  0  0  0
 32 33  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0152072

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC(=O)[C@@H]1C[C@H](OC(C)=O)C(=O)[C@H]2[C@@]1(C)CC[C@@H](C(O)=O)[C@]2(C)\C=C\C1=CC(=O)OC1O

> <INCHI_IDENTIFIER>
InChI=1S/C23H28O10/c1-11(24)32-15-10-14(21(30)31-4)23(3)8-6-13(19(27)28)22(2,18(23)17(15)26)7-5-12-9-16(25)33-20(12)29/h5,7,9,13-15,18,20,29H,6,8,10H2,1-4H3,(H,27,28)/b7-5+/t13-,14-,15-,18+,20?,22-,23-/m0/s1

> <INCHI_KEY>
JLLALLSXASKWMT-JYYNUABRSA-N

> <FORMULA>
C23H28O10

> <MOLECULAR_WEIGHT>
464.467

> <EXACT_MASS>
464.168247102

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
61

> <JCHEM_AVERAGE_POLARIZABILITY>
46.36754973479564

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1R,2R,4aR,5R,7S,8aS)-7-(acetyloxy)-1-[(E)-2-(2-hydroxy-5-oxo-2,5-dihydrofuran-3-yl)ethenyl]-5-(methoxycarbonyl)-1,4a-dimethyl-8-oxo-decahydronaphthalene-2-carboxylic acid

> <ALOGPS_LOGP>
1.20

> <JCHEM_LOGP>
1.382272334666666

> <ALOGPS_LOGS>
-3.32

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
7.446671687598762

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.027775174334776

> <JCHEM_PKA_STRONGEST_BASIC>
-4.282429877431462

> <JCHEM_POLAR_SURFACE_AREA>
153.5

> <JCHEM_REFRACTIVITY>
112.03539999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.24e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1R,2R,4aR,5R,7S,8aS)-7-(acetyloxy)-1-[(E)-2-(2-hydroxy-5-oxo-2H-furan-3-yl)ethenyl]-5-(methoxycarbonyl)-1,4a-dimethyl-8-oxo-hexahydro-2H-naphthalene-2-carboxylic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 02-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   02-SEP-22         0                                  
HETATM    1  C   UNK     0       1.334  -6.930   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       1.334  -5.390   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       2.667  -4.620   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       4.001  -5.390   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      -2.667   0.000   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       2.667   1.540   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       4.345   1.180   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       6.325   1.180   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       5.798   2.627   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       6.788   3.807   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       6.415   5.301   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       7.721   6.117   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       7.829   7.653   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0       8.901   5.127   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0       8.324   3.699   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       9.140   2.393   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       8.002  -0.000   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0       9.336  -0.770   0.000  0.00  0.00           O+0
HETATM   29  O   UNK     0       8.002   1.540   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       4.001  -3.850   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6   32                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8   12                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9                                                            
CONECT   12    7   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12   15   32                                                  
CONECT   15   14   16   17   26                                             
CONECT   16   15                                                            
CONECT   17   15   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20   24                                                  
CONECT   20   19   21                                                       
CONECT   21   20   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21   24                                                       
CONECT   24   23   19   25                                                  
CONECT   25   24                                                            
CONECT   26   15   27   30                                                  
CONECT   27   26   28   29                                                  
CONECT   28   27                                                            
CONECT   29   27                                                            
CONECT   30   26   31                                                       
CONECT   31   30   32                                                       
CONECT   32   31   14    5   33                                             
CONECT   33   32                                                            
MASTER        0    0    0    0    0    0    0    0   33    0   70    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₃H₂₈O₁₀

Average Mass

464.4670 Da

Monoisotopic Mass

464.16825 Da

IUPAC Name

(1R,2R,4aR,5R,7S,8aS)-7-(acetyloxy)-1-[(E)-2-(2-hydroxy-5-oxo-2,5-dihydrofuran-3-yl)ethenyl]-5-(methoxycarbonyl)-1,4a-dimethyl-8-oxo-decahydronaphthalene-2-carboxylic acid

Traditional Name

(1R,2R,4aR,5R,7S,8aS)-7-(acetyloxy)-1-[(E)-2-(2-hydroxy-5-oxo-2H-furan-3-yl)ethenyl]-5-(methoxycarbonyl)-1,4a-dimethyl-8-oxo-hexahydro-2H-naphthalene-2-carboxylic acid

CAS Registry Number

Not Available

SMILES

COC(=O)[C@@H]1C[C@H](OC(C)=O)C(=O)[C@H]2[C@@]1(C)CC[C@@H](C(O)=O)[C@]2(C)\C=C\C1=CC(=O)OC1O

InChI Identifier

InChI=1S/C23H28O10/c1-11(24)32-15-10-14(21(30)31-4)23(3)8-6-13(19(27)28)22(2,18(23)17(15)26)7-5-12-9-16(25)33-20(12)29/h5,7,9,13-15,18,20,29H,6,8,10H2,1-4H3,(H,27,28)/b7-5+/t13-,14-,15-,18+,20?,22-,23-/m0/s1

InChI Key

JLLALLSXASKWMT-JYYNUABRSA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Salvia divinorum	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as diterpene lactones. These are diterpenoids containing a lactone moiety.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Terpene lactones

Direct Parent

Diterpene lactones

Alternative Parents

Substituents

Clerodane diterpenoid
Diterpenoid
Diterpene lactone
Tetracarboxylic acid or derivatives
Alpha-acyloxy ketone
2-furanone
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Methyl ester
Dihydrofuran
Lactone
Ketone
Hemiacetal
Carboxylic acid ester
Oxacycle
Organoheterocyclic compound
Carboxylic acid
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic 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	1.2	ALOGPS
logP	1.38	ChemAxon
logS	-3.3	ALOGPS
pKa (Strongest Acidic)	4.03	ChemAxon
pKa (Strongest Basic)	-4.3	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	153.5 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	112.04 m³·mol⁻¹	ChemAxon
Polarizability	46.37 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	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

C00041822

Chemspider ID

17257432

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

16099523

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (1r,2r,4ar,5r,7s,8as)-7-(acetyloxy)-1-[(1e)-2-(2-hydroxy-5-oxo-2h-furan-3-yl)ethenyl]-5-(methoxycarbonyl)-1,4a-dimethyl-8-oxo-hexahydro-2h-naphthalene-2-carboxylic acid (NP0152072)

MOL for NP0152072 ((1r,2r,4ar,5r,7s,8as)-7-(acetyloxy)-1-[(1e)-2-(2-hydroxy-5-oxo-2h-furan-3-yl)ethenyl]-5-(methoxycarbonyl)-1,4a-dimethyl-8-oxo-hexahydro-2h-naphthalene-2-carboxylic acid)

3D MOL for NP0152072 ((1r,2r,4ar,5r,7s,8as)-7-(acetyloxy)-1-[(1e)-2-(2-hydroxy-5-oxo-2h-furan-3-yl)ethenyl]-5-(methoxycarbonyl)-1,4a-dimethyl-8-oxo-hexahydro-2h-naphthalene-2-carboxylic acid)

3D SDF for NP0152072 ((1r,2r,4ar,5r,7s,8as)-7-(acetyloxy)-1-[(1e)-2-(2-hydroxy-5-oxo-2h-furan-3-yl)ethenyl]-5-(methoxycarbonyl)-1,4a-dimethyl-8-oxo-hexahydro-2h-naphthalene-2-carboxylic acid)

3D-SDF for NP0152072 ((1r,2r,4ar,5r,7s,8as)-7-(acetyloxy)-1-[(1e)-2-(2-hydroxy-5-oxo-2h-furan-3-yl)ethenyl]-5-(methoxycarbonyl)-1,4a-dimethyl-8-oxo-hexahydro-2h-naphthalene-2-carboxylic acid)

PDB for NP0152072 ((1r,2r,4ar,5r,7s,8as)-7-(acetyloxy)-1-[(1e)-2-(2-hydroxy-5-oxo-2h-furan-3-yl)ethenyl]-5-(methoxycarbonyl)-1,4a-dimethyl-8-oxo-hexahydro-2h-naphthalene-2-carboxylic acid)

3D PDB for NP0152072 ((1r,2r,4ar,5r,7s,8as)-7-(acetyloxy)-1-[(1e)-2-(2-hydroxy-5-oxo-2h-furan-3-yl)ethenyl]-5-(methoxycarbonyl)-1,4a-dimethyl-8-oxo-hexahydro-2h-naphthalene-2-carboxylic acid)

SMILES for NP0152072 ((1r,2r,4ar,5r,7s,8as)-7-(acetyloxy)-1-[(1e)-2-(2-hydroxy-5-oxo-2h-furan-3-yl)ethenyl]-5-(methoxycarbonyl)-1,4a-dimethyl-8-oxo-hexahydro-2h-naphthalene-2-carboxylic acid)

INCHI for NP0152072 ((1r,2r,4ar,5r,7s,8as)-7-(acetyloxy)-1-[(1e)-2-(2-hydroxy-5-oxo-2h-furan-3-yl)ethenyl]-5-(methoxycarbonyl)-1,4a-dimethyl-8-oxo-hexahydro-2h-naphthalene-2-carboxylic acid)

Structure for NP0152072 ((1r,2r,4ar,5r,7s,8as)-7-(acetyloxy)-1-[(1e)-2-(2-hydroxy-5-oxo-2h-furan-3-yl)ethenyl]-5-(methoxycarbonyl)-1,4a-dimethyl-8-oxo-hexahydro-2h-naphthalene-2-carboxylic acid)

3D Structure for NP0152072 ((1r,2r,4ar,5r,7s,8as)-7-(acetyloxy)-1-[(1e)-2-(2-hydroxy-5-oxo-2h-furan-3-yl)ethenyl]-5-(methoxycarbonyl)-1,4a-dimethyl-8-oxo-hexahydro-2h-naphthalene-2-carboxylic acid)