NP-MRD: Showing NP-Card for 5,8a,9',14'-tetramethyl-4'-methylidene-5,6,7,8,9,9a-hexahydro-3ah-6'-oxaspiro[naphtho[2,3-b]furan-3,12'-tetracyclo[9.2.2.0¹,¹⁰.0³,⁷]pentadecane]-9',14'-diene-2,5'-dione (NP0323978)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-09-12 03:44:55 UTC

Updated at

2022-09-12 03:44:55 UTC

NP-MRD ID

NP0323978

Secondary Accession Numbers

None

Natural Product Identification

Common Name

5,8a,9',14'-tetramethyl-4'-methylidene-5,6,7,8,9,9a-hexahydro-3ah-6'-oxaspiro[naphtho[2,3-b]furan-3,12'-tetracyclo[9.2.2.0¹,¹⁰.0³,⁷]pentadecane]-9',14'-diene-2,5'-dione

Description

5,8A,9',14'-tetramethyl-4'-methylidene-3a,5,6,7,8,8a,9,9a-octahydro-2H-6'-oxaspiro[naphtho[2,3-b]furan-3,12'-tetracyclo[9.2.2.0¹,¹⁰.0³,⁷]Pentadecane]-9',14'-diene-2,5'-dione belongs to the class of organic compounds known as eudesmanolides, secoeudesmanolides, and derivatives. These are terpenoids with a structure based on the eudesmanolide (a 3,5a,9-trimethyl-naphtho[1,2-b]furan-2-one derivative) or secoeudesmanolide (a 3,6-dimethyl-5-(pentan-2-yl)-1-benzofuran-2-one derivative) skeleton. 5,8a,9',14'-tetramethyl-4'-methylidene-5,6,7,8,9,9a-hexahydro-3ah-6'-oxaspiro[naphtho[2,3-b]furan-3,12'-tetracyclo[9.2.2.0¹,¹⁰.0³,⁷]pentadecane]-9',14'-diene-2,5'-dione is found in Rudbeckia laciniata. 5,8A,9',14'-tetramethyl-4'-methylidene-3a,5,6,7,8,8a,9,9a-octahydro-2H-6'-oxaspiro[naphtho[2,3-b]furan-3,12'-tetracyclo[9.2.2.0¹,¹⁰.0³,⁷]Pentadecane]-9',14'-diene-2,5'-dione is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004231522492D          

 34 40  0  0  0  0            999 V2000
    4.1988    2.3358    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2158    1.3661    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0385    1.3046    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3966    0.5614    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9321   -0.1203    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1094   -0.0589    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5238   -0.8762    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6448   -0.7406    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8221   -0.6792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2259   -1.2494    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3996   -0.7981    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6427   -1.2839    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5467    0.0137    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8776    0.7451    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3073    1.3412    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9719    1.8301    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7685    1.6152    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1577    0.9583    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7710    0.2295    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8996   -0.0223    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2751    0.5169    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8450   -0.2427    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2747    0.3535    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5059    1.1455    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0979    1.7595    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8918   -0.8950    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9184    0.9373    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0972    1.7427    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8731    2.2602    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3866    2.1617    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0830    2.9806    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4639    0.0640    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9285    0.7458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7512    0.6843    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  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  6  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 11 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 15 21  1  0  0  0  0
 21 22  1  0  0  0  0
 13 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  2  0  0  0  0
 15 24  1  0  0  0  0
 24 25  1  0  0  0  0
 20 26  1  0  0  0  0
 18 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
 17 30  1  0  0  0  0
 30 31  2  0  0  0  0
 13 32  1  0  0  0  0
  9 32  1  0  0  0  0
 32 33  1  0  0  0  0
 33 34  2  0  0  0  0
  2 34  1  0  0  0  0
  6 34  1  0  0  0  0
M  END

     RDKit          3D

 70 76  0  0  0  0  0  0  0  0999 V2000
    6.3509    1.7252    1.0157 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8965    0.5156    0.7958 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6027   -0.7021    1.1680 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7250   -0.7699    1.7721 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8330   -1.7933    0.7458 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5039   -1.3365    0.7087 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.6832   -2.2090   -0.1537 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2921   -1.8396   -0.3749 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4421   -2.9150   -0.9519 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7279   -0.7012   -0.1580 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2670   -0.3408   -0.4007 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.5594    0.8820   -1.2379 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6490    1.4886   -0.7776 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3115    2.7379   -1.1824 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1625    0.6043    0.3490 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.5170    0.8561    0.7424 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6315    0.0712    0.1553 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.1169    0.8491    1.4495 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1243    0.0939    0.9456 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.3531   -0.9638    1.9490 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1050   -2.1333    1.9149 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1672   -0.3726    2.9061 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1667    0.3152    2.1639 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.1646   -0.6894    1.7225 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5759   -0.6790    0.2985 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.0659   -1.9616   -0.3836 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0940   -0.8363    0.2814 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7049   -0.6244   -1.0603 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3517    0.8131   -1.4691 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8772    0.7687   -1.8065 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.4846    2.1392   -2.3052 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1315    0.4523   -0.5203 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1051    1.1877   -0.1532 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3603    0.9283    1.0625 C   0  0  2  0  0  0  0  0  0  0  0  0
    7.2909    1.8982    1.4933 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7583    2.5643    0.7045 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1277   -1.2619    1.7485 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1782   -2.2997   -1.1645 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7595   -3.2600    0.2549 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7208   -2.5709   -1.7076 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0347   -3.5554   -0.1661 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1334   -3.6011   -1.5505 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3046   -1.0812   -0.8988 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0178    1.2137   -2.0853 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3971    3.3822   -0.2602 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7458    3.2383   -1.9771 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3698    2.5906   -1.5165 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7724    1.9454    0.5730 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6125    0.7558    1.8662 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6831    0.0798   -0.9385 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5393    0.4305    2.3583 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9237    1.9169    1.5578 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6277    1.1244    2.7719 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8366   -1.7421    1.9931 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0567   -0.5525    2.4135 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1139   -2.2858    0.0781 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8922   -1.7154   -1.4475 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8176   -2.7793   -0.2946 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3139   -1.8276    0.7251 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5000   -0.0749    0.9856 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7830   -0.7586   -0.9748 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2366   -1.3602   -1.7683 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4491    1.4313   -0.5370 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9638    1.1720   -2.2950 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7255   -0.0182   -2.5526 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5282    2.8559   -1.4786 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4811    2.1384   -2.7434 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2444    2.4658   -3.0532 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7906    2.0456   -0.7817 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0139    1.9350    1.4565 H   0  0  0  0  0  0  0  0  0  0  0  0
 31 30  1  0
 30 29  1  0
 29 28  1  0
 28 27  1  0
 27 25  1  0
 25 26  1  6
 25 24  1  0
 24 23  1  0
 23 22  1  0
 22 20  1  0
 20 21  2  0
 19 20  1  1
 19 18  1  0
 18 15  1  0
 15 16  1  0
 16 17  1  0
 17  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  8 10  2  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
  6  5  1  0
  5  3  1  0
  3  4  2  0
  3  2  1  0
  2  1  2  3
 19 34  1  0
 34 33  1  0
 33 32  2  0
 32 30  1  0
 32 25  1  0
 34 23  1  0
 11 19  1  0
 10 15  1  0
 15 13  1  6
  2 17  1  0
 31 66  1  0
 31 67  1  0
 31 68  1  0
 30 65  1  6
 29 63  1  0
 29 64  1  0
 28 61  1  0
 28 62  1  0
 27 59  1  0
 27 60  1  0
 26 56  1  0
 26 57  1  0
 26 58  1  0
 24 54  1  0
 24 55  1  0
 23 53  1  1
 18 51  1  0
 18 52  1  0
 16 48  1  0
 16 49  1  0
 17 50  1  6
  6 37  1  1
  7 38  1  0
  7 39  1  0
  9 40  1  0
  9 41  1  0
  9 42  1  0
 11 43  1  6
 12 44  1  0
 14 45  1  0
 14 46  1  0
 14 47  1  0
  1 35  1  0
  1 36  1  0
 34 70  1  1
 33 69  1  0
M  END


  Mrv1533004231522492D          

 34 40  0  0  0  0            999 V2000
    4.1988    2.3358    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2158    1.3661    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0385    1.3046    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3966    0.5614    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9321   -0.1203    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1094   -0.0589    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5238   -0.8762    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6448   -0.7406    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8221   -0.6792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2259   -1.2494    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3996   -0.7981    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6427   -1.2839    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5467    0.0137    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8776    0.7451    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3073    1.3412    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9719    1.8301    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7685    1.6152    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1577    0.9583    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7710    0.2295    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8996   -0.0223    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2751    0.5169    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8450   -0.2427    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2747    0.3535    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5059    1.1455    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0979    1.7595    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8918   -0.8950    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9184    0.9373    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0972    1.7427    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8731    2.2602    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3866    2.1617    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0830    2.9806    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4639    0.0640    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9285    0.7458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7512    0.6843    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  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  6  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 11 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 15 21  1  0  0  0  0
 21 22  1  0  0  0  0
 13 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  2  0  0  0  0
 15 24  1  0  0  0  0
 24 25  1  0  0  0  0
 20 26  1  0  0  0  0
 18 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
 17 30  1  0  0  0  0
 30 31  2  0  0  0  0
 13 32  1  0  0  0  0
  9 32  1  0  0  0  0
 32 33  1  0  0  0  0
 33 34  2  0  0  0  0
  2 34  1  0  0  0  0
  6 34  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0323978

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1CCCC2(C)CC3OC(=O)C4(CC56CC7C(CC(C)=C5C4C=C6C)OC(=O)C7=C)C3C=C12

> <INCHI_IDENTIFIER>
InChI=1S/C30H36O4/c1-15-7-6-8-28(5)13-24-21(11-20(15)28)30(27(32)34-24)14-29-12-19-18(4)26(31)33-23(19)9-16(2)25(29)22(30)10-17(29)3/h10-11,15,19,21-24H,4,6-9,12-14H2,1-3,5H3

> <INCHI_KEY>
VTYHWQDFBOOIRA-UHFFFAOYSA-N

> <FORMULA>
C30H36O4

> <MOLECULAR_WEIGHT>
460.614

> <EXACT_MASS>
460.261359639

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
70

> <JCHEM_AVERAGE_POLARIZABILITY>
51.663024302716344

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
5,8a,9',14'-tetramethyl-4'-methylidene-3a,5,6,7,8,8a,9,9a-octahydro-2H-6'-oxaspiro[naphtho[2,3-b]furan-3,12'-tetracyclo[9.2.2.0¹,¹⁰.0³,⁷]pentadecane]-9',14'-diene-2,5'-dione

> <ALOGPS_LOGP>
5.13

> <JCHEM_LOGP>
4.878085987333334

> <ALOGPS_LOGS>
-5.41

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
7

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-6.679947927494666

> <JCHEM_POLAR_SURFACE_AREA>
52.6

> <JCHEM_REFRACTIVITY>
131.51059999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.79e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
5,8a,9',14'-tetramethyl-4'-methylidene-5,6,7,8,9,9a-hexahydro-3aH-6'-oxaspiro[naphtho[2,3-b]furan-3,12'-tetracyclo[9.2.2.0¹,¹⁰.0³,⁷]pentadecane]-9',14'-diene-2,5'-dione

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 23-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-APR-15         0                                  
HETATM    1  C   UNK     0       7.838   4.360   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       7.870   2.550   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       9.405   2.435   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      10.074   1.048   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       9.207  -0.225   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       7.671  -0.110   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       8.444  -1.636   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       6.804  -1.383   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.268  -1.268   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       4.155  -2.332   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       2.613  -1.490   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       1.200  -2.397   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       2.887   0.026   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       3.505   1.391   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       2.440   2.504   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       3.681   3.416   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       5.168   3.015   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       5.894   1.789   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       5.173   0.428   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       3.546  -0.042   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       2.380   0.965   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       1.577  -0.453   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       0.513   0.660   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       0.944   2.138   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      -0.183   3.284   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       3.531  -1.671   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0       7.314   1.750   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0       7.648   3.253   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0       9.097   4.219   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0       6.322   4.035   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       5.755   5.564   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       4.599   0.120   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       5.467   1.392   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       7.002   1.277   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   34                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7    8   34                                             
CONECT    7    6                                                            
CONECT    8    6    9                                                       
CONECT    9    8   10   32                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14   22   32                                             
CONECT   14   13   15                                                       
CONECT   15   14   16   21   24                                             
CONECT   16   15   17                                                       
CONECT   17   16   18   30                                                  
CONECT   18   17   19   27                                                  
CONECT   19   18   20                                                       
CONECT   20   19   21   26                                                  
CONECT   21   20   15   22                                                  
CONECT   22   21   13   23                                                  
CONECT   23   22   24                                                       
CONECT   24   23   15   25                                                  
CONECT   25   24                                                            
CONECT   26   20                                                            
CONECT   27   18   28                                                       
CONECT   28   27   29   30                                                  
CONECT   29   28                                                            
CONECT   30   28   17   31                                                  
CONECT   31   30                                                            
CONECT   32   13    9   33                                                  
CONECT   33   32   34                                                       
CONECT   34   33    2    6                                                  
MASTER        0    0    0    0    0    0    0    0   34    0   80    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₃₀H₃₆O₄

Average Mass

460.6140 Da

Monoisotopic Mass

460.26136 Da

IUPAC Name

5,8a,9',14'-tetramethyl-4'-methylidene-3a,5,6,7,8,8a,9,9a-octahydro-2H-6'-oxaspiro[naphtho[2,3-b]furan-3,12'-tetracyclo[9.2.2.0¹,¹⁰.0³,⁷]pentadecane]-9',14'-diene-2,5'-dione

Traditional Name

5,8a,9',14'-tetramethyl-4'-methylidene-5,6,7,8,9,9a-hexahydro-3aH-6'-oxaspiro[naphtho[2,3-b]furan-3,12'-tetracyclo[9.2.2.0¹,¹⁰.0³,⁷]pentadecane]-9',14'-diene-2,5'-dione

CAS Registry Number

Not Available

SMILES

CC1CCCC2(C)CC3OC(=O)C4(CC56CC7C(CC(C)=C5C4C=C6C)OC(=O)C7=C)C3C=C12

InChI Identifier

InChI=1S/C30H36O4/c1-15-7-6-8-28(5)13-24-21(11-20(15)28)30(27(32)34-24)14-29-12-19-18(4)26(31)33-23(19)9-16(2)25(29)22(30)10-17(29)3/h10-11,15,19,21-24H,4,6-9,12-14H2,1-3,5H3

InChI Key

VTYHWQDFBOOIRA-UHFFFAOYSA-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
Rudbeckia laciniata	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as eudesmanolides, secoeudesmanolides, and derivatives. These are terpenoids with a structure based on the eudesmanolide (a 3,5a,9-trimethyl-naphtho[1,2-b]furan-2-one derivative) or secoeudesmanolide (a 3,6-dimethyl-5-(pentan-2-yl)-1-benzofuran-2-one derivative) skeleton.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Terpene lactones

Direct Parent

Eudesmanolides, secoeudesmanolides, and derivatives

Alternative Parents

Substituents

Eudesmanolide
Sesquiterpenoid
Naphthofuran
Dicarboxylic acid or derivatives
Gamma butyrolactone
Tetrahydrofuran
Enoate ester
Alpha,beta-unsaturated carboxylic ester
Lactone
Carboxylic acid ester
Organoheterocyclic compound
Oxacycle
Carboxylic acid derivative
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Organic oxygen 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	5.13	ALOGPS
logP	4.88	ChemAxon
logS	-5.4	ALOGPS
pKa (Strongest Basic)	-6.7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	52.6 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	131.51 m³·mol⁻¹	ChemAxon
Polarizability	51.66 Å³	ChemAxon
Number of Rings	7	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 5,8a,9',14'-tetramethyl-4'-methylidene-5,6,7,8,9,9a-hexahydro-3ah-6'-oxaspiro[naphtho[2,3-b]furan-3,12'-tetracyclo[9.2.2.0¹,¹⁰.0³,⁷]pentadecane]-9',14'-diene-2,5'-dione (NP0323978)

MOL for NP0323978 (5,8a,9',14'-tetramethyl-4'-methylidene-5,6,7,8,9,9a-hexahydro-3ah-6'-oxaspiro[naphtho[2,3-b]furan-3,12'-tetracyclo[9.2.2.0¹,¹⁰.0³,⁷]pentadecane]-9',14'-diene-2,5'-dione)

3D MOL for NP0323978 (5,8a,9',14'-tetramethyl-4'-methylidene-5,6,7,8,9,9a-hexahydro-3ah-6'-oxaspiro[naphtho[2,3-b]furan-3,12'-tetracyclo[9.2.2.0¹,¹⁰.0³,⁷]pentadecane]-9',14'-diene-2,5'-dione)

3D SDF for NP0323978 (5,8a,9',14'-tetramethyl-4'-methylidene-5,6,7,8,9,9a-hexahydro-3ah-6'-oxaspiro[naphtho[2,3-b]furan-3,12'-tetracyclo[9.2.2.0¹,¹⁰.0³,⁷]pentadecane]-9',14'-diene-2,5'-dione)

3D-SDF for NP0323978 (5,8a,9',14'-tetramethyl-4'-methylidene-5,6,7,8,9,9a-hexahydro-3ah-6'-oxaspiro[naphtho[2,3-b]furan-3,12'-tetracyclo[9.2.2.0¹,¹⁰.0³,⁷]pentadecane]-9',14'-diene-2,5'-dione)

PDB for NP0323978 (5,8a,9',14'-tetramethyl-4'-methylidene-5,6,7,8,9,9a-hexahydro-3ah-6'-oxaspiro[naphtho[2,3-b]furan-3,12'-tetracyclo[9.2.2.0¹,¹⁰.0³,⁷]pentadecane]-9',14'-diene-2,5'-dione)

3D PDB for NP0323978 (5,8a,9',14'-tetramethyl-4'-methylidene-5,6,7,8,9,9a-hexahydro-3ah-6'-oxaspiro[naphtho[2,3-b]furan-3,12'-tetracyclo[9.2.2.0¹,¹⁰.0³,⁷]pentadecane]-9',14'-diene-2,5'-dione)

SMILES for NP0323978 (5,8a,9',14'-tetramethyl-4'-methylidene-5,6,7,8,9,9a-hexahydro-3ah-6'-oxaspiro[naphtho[2,3-b]furan-3,12'-tetracyclo[9.2.2.0¹,¹⁰.0³,⁷]pentadecane]-9',14'-diene-2,5'-dione)

INCHI for NP0323978 (5,8a,9',14'-tetramethyl-4'-methylidene-5,6,7,8,9,9a-hexahydro-3ah-6'-oxaspiro[naphtho[2,3-b]furan-3,12'-tetracyclo[9.2.2.0¹,¹⁰.0³,⁷]pentadecane]-9',14'-diene-2,5'-dione)

Structure for NP0323978 (5,8a,9',14'-tetramethyl-4'-methylidene-5,6,7,8,9,9a-hexahydro-3ah-6'-oxaspiro[naphtho[2,3-b]furan-3,12'-tetracyclo[9.2.2.0¹,¹⁰.0³,⁷]pentadecane]-9',14'-diene-2,5'-dione)

3D Structure for NP0323978 (5,8a,9',14'-tetramethyl-4'-methylidene-5,6,7,8,9,9a-hexahydro-3ah-6'-oxaspiro[naphtho[2,3-b]furan-3,12'-tetracyclo[9.2.2.0¹,¹⁰.0³,⁷]pentadecane]-9',14'-diene-2,5'-dione)