NP-MRD: Showing NP-Card for (1's,2r,6'r,7's,9'r,11's,13's)-7'-(acetyloxy)-11'-(furan-3-yl)-9',13'-dimethyl-4'-oxo-10',14'-dioxaspiro[oxirane-2,5'-tetracyclo[9.2.1.0¹,⁶.0⁹,¹³]tetradecan]-6'-ylmethyl acetate (NP0211465)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-09-05 09:45:17 UTC

Updated at

2022-09-05 09:45:18 UTC

NP-MRD ID

NP0211465

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1's,2r,6'r,7's,9'r,11's,13's)-7'-(acetyloxy)-11'-(furan-3-yl)-9',13'-dimethyl-4'-oxo-10',14'-dioxaspiro[oxirane-2,5'-tetracyclo[9.2.1.0¹,⁶.0⁹,¹³]tetradecan]-6'-ylmethyl acetate

Description

Teucrolivin H belongs to the class of organic compounds known as naphthofurans. Naphthofurans are compounds containing a furan ring fused to a naphthalene moiety. Furan is a 5 membered- ring aromatic ring with four carbon and one oxygen atoms. Naphthalene is a polycyclic aromatic hydrocarbon made up of two fused benzene rings. (1's,2r,6'r,7's,9'r,11's,13's)-7'-(acetyloxy)-11'-(furan-3-yl)-9',13'-dimethyl-4'-oxo-10',14'-dioxaspiro[oxirane-2,5'-tetracyclo[9.2.1.0¹,⁶.0⁹,¹³]tetradecan]-6'-ylmethyl acetate is found in Teucrium oliverianum and Teucrium orientale. (1's,2r,6'r,7's,9'r,11's,13's)-7'-(acetyloxy)-11'-(furan-3-yl)-9',13'-dimethyl-4'-oxo-10',14'-dioxaspiro[oxirane-2,5'-tetracyclo[9.2.1.0¹,⁶.0⁹,¹³]tetradecan]-6'-ylmethyl acetate was first documented in 2004 (PMID: 15577256). Based on a literature review very few articles have been published on Teucrolivin H.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309052211452D          

 33 38  0  0  1  0            999 V2000
    6.1266   -0.1558    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3030   -0.1080    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8498   -0.7974    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9325    0.6291    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9026    0.6888    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4243    1.5057    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.4378    0.6582    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.9631   -0.1721    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6051   -0.9563    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0837   -1.6283    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7838   -1.0349    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6970    0.2800    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9650    0.7426    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4947    0.0075    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1355    0.8494    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1077    1.7232    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.3421    2.0307    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3566    1.5920    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9897    2.1209    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6823    2.8865    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1408    2.8307    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3926    2.2376    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0950    1.5363    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.7697    1.1485    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7034    2.0413    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.0094    2.8246    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8100    3.0936    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4234    2.5392    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1225    3.0484    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2442    1.7356    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.0517    1.5663    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5014    0.9517    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8856    2.4857    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  2  4  1  0  0  0  0
  4  5  1  0  0  0  0
  6  5  1  1  0  0  0
  6  7  1  0  0  0  0
  7  8  1  1  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  1  0  0  0  0
 13 14  1  6  0  0  0
 13 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  6  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 17 21  2  0  0  0  0
 16 22  1  0  0  0  0
 22 23  1  0  0  0  0
 13 23  1  0  0  0  0
 23 24  1  1  0  0  0
 23 25  1  0  0  0  0
  6 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  2  0  0  0  0
 28 30  1  0  0  0  0
  6 30  1  0  0  0  0
 30 31  1  0  0  0  0
 31 32  1  0  0  0  0
 30 32  1  1  0  0  0
 25 33  1  6  0  0  0
 16 33  1  0  0  0  0
M  END

     RDKit          2D

 61 66  0  0  0  0  0  0  0  0999 V2000
    1.8170   -3.1471    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0670   -1.8481    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4330   -1.8481    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8170   -0.5490    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0670    0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3170    2.0490    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8170    2.0490    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2265    1.5360    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3756    2.5002    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7851    1.9872    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2971    3.9981    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5670    3.3481    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8170    4.6471    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5670    5.9462    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7275    5.6782    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0570    5.1517    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3561    5.9017    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5129    7.3935    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9801    7.7054    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7301    6.4063    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7264    5.2916    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6867    5.7618    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3170    4.6471    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9271    6.0174    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4330    3.3481    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9330    3.3481    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6830    2.0490    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9330    0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6830   -0.5490    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4330    0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8660    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4330   -0.7500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9002    3.6599    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5670   -4.4462    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5179   -3.8971    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1160   -2.3971    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5485    0.9845    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2722   -0.5222    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1033    0.5766    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1947    1.4741    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2982    3.3967    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2721    0.5776    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7161    4.3123    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9152    2.6906    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3170    7.2452    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9478    5.3601    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7722    7.2183    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3981    8.3972    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5902    9.0757    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0383    3.8244    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4367    7.0609    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1301    7.0199    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3656    7.4519    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4432    6.6275    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4043    5.7570    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3426    3.8611    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3228    4.7184    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8321    1.0849    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8321    3.0132    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0796    0.8816    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5235   -1.3482    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  1  0
  4  5  1  0
  6  5  1  6
  6  7  1  0
  7 12  1  0
 12 13  1  0
 13 14  1  1
 13 15  1  0
 15 16  1  0
 16 22  1  0
 22 23  1  0
 23 24  1  6
 23 25  1  0
 25 26  1  0
 26 27  1  0
 27 28  1  0
 28 29  2  0
 28 30  1  0
 30 31  1  0
 31 32  1  0
 25 33  1  1
 16 17  1  1
 17 21  2  0
 21 20  1  0
 20 19  1  0
 19 18  2  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
  9 11  2  0
 25  6  1  0
 30 32  1  6
 18 17  1  0
 30  6  1  0
 23 13  1  0
 33 16  1  0
  1 34  1  0
  1 35  1  0
  1 36  1  0
  5 37  1  0
  5 38  1  0
  7 39  1  1
 12 43  1  0
 12 44  1  0
 14 45  1  0
 14 46  1  0
 14 47  1  0
 22 51  1  0
 22 52  1  0
 24 53  1  0
 24 54  1  0
 24 55  1  0
 26 56  1  0
 26 57  1  0
 27 58  1  0
 27 59  1  0
 31 60  1  0
 31 61  1  0
 21 50  1  0
 19 49  1  0
 18 48  1  0
 10 40  1  0
 10 41  1  0
 10 42  1  0
M  END


  Mrv1652309052211452D          

 33 38  0  0  1  0            999 V2000
    6.1266   -0.1558    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3030   -0.1080    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8498   -0.7974    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9325    0.6291    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9026    0.6888    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4243    1.5057    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.4378    0.6582    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.9631   -0.1721    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6051   -0.9563    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0837   -1.6283    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7838   -1.0349    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6970    0.2800    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9650    0.7426    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4947    0.0075    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1355    0.8494    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1077    1.7232    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.3421    2.0307    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3566    1.5920    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9897    2.1209    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6823    2.8865    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1408    2.8307    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3926    2.2376    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0950    1.5363    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.7697    1.1485    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7034    2.0413    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.0094    2.8246    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8100    3.0936    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4234    2.5392    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1225    3.0484    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2442    1.7356    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.0517    1.5663    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5014    0.9517    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8856    2.4857    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  2  4  1  0  0  0  0
  4  5  1  0  0  0  0
  6  5  1  1  0  0  0
  6  7  1  0  0  0  0
  7  8  1  1  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  1  0  0  0  0
 13 14  1  6  0  0  0
 13 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  6  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 17 21  2  0  0  0  0
 16 22  1  0  0  0  0
 22 23  1  0  0  0  0
 13 23  1  0  0  0  0
 23 24  1  1  0  0  0
 23 25  1  0  0  0  0
  6 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  2  0  0  0  0
 28 30  1  0  0  0  0
  6 30  1  0  0  0  0
 30 31  1  0  0  0  0
 31 32  1  0  0  0  0
 30 32  1  1  0  0  0
 25 33  1  6  0  0  0
 16 33  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0211465

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(=O)OC[C@@]12[C@H](C[C@@]3(C)O[C@]4(C[C@]3(C)[C@]1(CCC(=O)[C@]21CO1)O4)C1=COC=C1)OC(C)=O

> <INCHI_IDENTIFIER>
InChI=1S/C24H28O9/c1-14(25)29-12-21-18(31-15(2)26)9-20(4)19(3)11-23(32-20,16-6-8-28-10-16)33-24(19,21)7-5-17(27)22(21)13-30-22/h6,8,10,18H,5,7,9,11-13H2,1-4H3/t18-,19-,20+,21-,22+,23-,24-/m0/s1

> <INCHI_KEY>
PVDDMXMYNHAGMK-KRFDGIDSSA-N

> <FORMULA>
C24H28O9

> <MOLECULAR_WEIGHT>
460.479

> <EXACT_MASS>
460.173332482

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
61

> <JCHEM_AVERAGE_POLARIZABILITY>
46.62789652931602

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
[(1'S,2R,6'R,7'S,9'R,11'S,13'S)-7'-(acetyloxy)-11'-(furan-3-yl)-9',13'-dimethyl-4'-oxo-10',14'-dioxaspiro[oxirane-2,5'-tetracyclo[9.2.1.0^{1,6}.0^{9,13}]tetradecane]-6'-yl]methyl acetate

> <JCHEM_LOGP>
1.388803532333332

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
16.612412558161303

> <JCHEM_PKA_STRONGEST_BASIC>
-2.858547373184602

> <JCHEM_POLAR_SURFACE_AREA>
113.8

> <JCHEM_REFRACTIVITY>
109.28909999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(1'S,2R,6'R,7'S,9'R,11'S,13'S)-7'-(acetyloxy)-11'-(furan-3-yl)-9',13'-dimethyl-4'-oxo-10',14'-dioxaspiro[oxirane-2,5'-tetracyclo[9.2.1.0^{1,6}.0^{9,13}]tetradecane]-6'-ylmethyl acetate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 05-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   05-SEP-22         0                                  
HETATM    1  C   UNK     0      11.436  -0.291   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       9.899  -0.202   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       9.053  -1.489   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0       9.207   1.174   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       7.285   1.286   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       6.392   2.811   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.417   1.229   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       7.398  -0.321   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       6.730  -1.785   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       7.623  -3.040   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       5.197  -1.932   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       5.034   0.523   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       3.668   1.386   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.790   0.014   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       2.120   1.586   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       2.068   3.217   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       0.639   3.791   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -0.666   2.972   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -1.847   3.959   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0      -1.274   5.388   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       0.263   5.284   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       2.599   4.177   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       3.911   2.868   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       5.170   2.144   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       5.046   3.810   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       5.618   5.273   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       7.112   5.775   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       8.257   4.740   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0       9.562   5.690   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0       7.923   3.240   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       9.430   2.924   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0       8.403   1.776   0.000  0.00  0.00           O+0
HETATM   33  O   UNK     0       3.520   4.640   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7   25   30                                             
CONECT    7    6    8   12                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9                                                            
CONECT   12    7   13                                                       
CONECT   13   12   14   15   23                                             
CONECT   14   13                                                            
CONECT   15   13   16                                                       
CONECT   16   15   17   22   33                                             
CONECT   17   16   18   21                                                  
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   17                                                       
CONECT   22   16   23                                                       
CONECT   23   22   13   24   25                                             
CONECT   24   23                                                            
CONECT   25   23    6   26   33                                             
CONECT   26   25   27                                                       
CONECT   27   26   28                                                       
CONECT   28   27   29   30                                                  
CONECT   29   28                                                            
CONECT   30   28    6   31   32                                             
CONECT   31   30   32                                                       
CONECT   32   31   30                                                       
CONECT   33   25   16                                                       
MASTER        0    0    0    0    0    0    0    0   33    0   76    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₄H₂₈O₉

Average Mass

460.4790 Da

Monoisotopic Mass

460.17333 Da

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

CC(=O)OC[C@@]12[C@H](C[C@@]3(C)O[C@]4(C[C@]3(C)[C@]1(CCC(=O)[C@]21CO1)O4)C1=COC=C1)OC(C)=O

InChI Identifier

InChI=1S/C24H28O9/c1-14(25)29-12-21-18(31-15(2)26)9-20(4)19(3)11-23(32-20,16-6-8-28-10-16)33-24(19,21)7-5-17(27)22(21)13-30-22/h6,8,10,18H,5,7,9,11-13H2,1-4H3/t18-,19-,20+,21-,22+,23-,24-/m0/s1

InChI Key

PVDDMXMYNHAGMK-KRFDGIDSSA-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
Teucrium oliverianum	LOTUS Database	35616633
Teucrium orientale	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as naphthofurans. Naphthofurans are compounds containing a furan ring fused to a naphthalene moiety. Furan is a 5 membered- ring aromatic ring with four carbon and one oxygen atoms. Naphthalene is a polycyclic aromatic hydrocarbon made up of two fused benzene rings.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Naphthofurans

Sub Class

Not Available

Direct Parent

Naphthofurans

Alternative Parents

Substituents

Naphthofuran
Ketal
Dicarboxylic acid or derivatives
Meta-dioxane
Heteroaromatic compound
Tetrahydrofuran
Furan
Ketone
Carboxylic acid ester
Oxacycle
Ether
Oxirane
Dialkyl ether
Carboxylic acid derivative
Acetal
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
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

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00032314

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

101357807

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Bruno M, Rosselli S, Maggio A, Piozzi F, Scaglioni L, Arnold NA, Simmonds MS: Neoclerodanes from Teucrium orientale. Chem Pharm Bull (Tokyo). 2004 Dec;52(12):1497-500. doi: 10.1248/cpb.52.1497. [PubMed:15577256 ]
LOTUS database [Link]

Showing NP-Card for (1's,2r,6'r,7's,9'r,11's,13's)-7'-(acetyloxy)-11'-(furan-3-yl)-9',13'-dimethyl-4'-oxo-10',14'-dioxaspiro[oxirane-2,5'-tetracyclo[9.2.1.0¹,⁶.0⁹,¹³]tetradecan]-6'-ylmethyl acetate (NP0211465)

MOL for NP0211465 ((1's,2r,6'r,7's,9'r,11's,13's)-7'-(acetyloxy)-11'-(furan-3-yl)-9',13'-dimethyl-4'-oxo-10',14'-dioxaspiro[oxirane-2,5'-tetracyclo[9.2.1.0¹,⁶.0⁹,¹³]tetradecan]-6'-ylmethyl acetate)

3D MOL for NP0211465 ((1's,2r,6'r,7's,9'r,11's,13's)-7'-(acetyloxy)-11'-(furan-3-yl)-9',13'-dimethyl-4'-oxo-10',14'-dioxaspiro[oxirane-2,5'-tetracyclo[9.2.1.0¹,⁶.0⁹,¹³]tetradecan]-6'-ylmethyl acetate)

3D SDF for NP0211465 ((1's,2r,6'r,7's,9'r,11's,13's)-7'-(acetyloxy)-11'-(furan-3-yl)-9',13'-dimethyl-4'-oxo-10',14'-dioxaspiro[oxirane-2,5'-tetracyclo[9.2.1.0¹,⁶.0⁹,¹³]tetradecan]-6'-ylmethyl acetate)

3D-SDF for NP0211465 ((1's,2r,6'r,7's,9'r,11's,13's)-7'-(acetyloxy)-11'-(furan-3-yl)-9',13'-dimethyl-4'-oxo-10',14'-dioxaspiro[oxirane-2,5'-tetracyclo[9.2.1.0¹,⁶.0⁹,¹³]tetradecan]-6'-ylmethyl acetate)

PDB for NP0211465 ((1's,2r,6'r,7's,9'r,11's,13's)-7'-(acetyloxy)-11'-(furan-3-yl)-9',13'-dimethyl-4'-oxo-10',14'-dioxaspiro[oxirane-2,5'-tetracyclo[9.2.1.0¹,⁶.0⁹,¹³]tetradecan]-6'-ylmethyl acetate)

3D PDB for NP0211465 ((1's,2r,6'r,7's,9'r,11's,13's)-7'-(acetyloxy)-11'-(furan-3-yl)-9',13'-dimethyl-4'-oxo-10',14'-dioxaspiro[oxirane-2,5'-tetracyclo[9.2.1.0¹,⁶.0⁹,¹³]tetradecan]-6'-ylmethyl acetate)

SMILES for NP0211465 ((1's,2r,6'r,7's,9'r,11's,13's)-7'-(acetyloxy)-11'-(furan-3-yl)-9',13'-dimethyl-4'-oxo-10',14'-dioxaspiro[oxirane-2,5'-tetracyclo[9.2.1.0¹,⁶.0⁹,¹³]tetradecan]-6'-ylmethyl acetate)

INCHI for NP0211465 ((1's,2r,6'r,7's,9'r,11's,13's)-7'-(acetyloxy)-11'-(furan-3-yl)-9',13'-dimethyl-4'-oxo-10',14'-dioxaspiro[oxirane-2,5'-tetracyclo[9.2.1.0¹,⁶.0⁹,¹³]tetradecan]-6'-ylmethyl acetate)

Structure for NP0211465 ((1's,2r,6'r,7's,9'r,11's,13's)-7'-(acetyloxy)-11'-(furan-3-yl)-9',13'-dimethyl-4'-oxo-10',14'-dioxaspiro[oxirane-2,5'-tetracyclo[9.2.1.0¹,⁶.0⁹,¹³]tetradecan]-6'-ylmethyl acetate)

3D Structure for NP0211465 ((1's,2r,6'r,7's,9'r,11's,13's)-7'-(acetyloxy)-11'-(furan-3-yl)-9',13'-dimethyl-4'-oxo-10',14'-dioxaspiro[oxirane-2,5'-tetracyclo[9.2.1.0¹,⁶.0⁹,¹³]tetradecan]-6'-ylmethyl acetate)