NP-MRD: Showing NP-Card for (1s,3r,12r,15r,16s,18r)-11,11,15-trimethyl-1,16,18-tris(3-methylbut-2-en-1-yl)-20-oxapentacyclo[16.2.1.0³,¹².0³,¹⁵.0⁵,¹⁰]henicosa-5,7,9-triene-2,4,19,21-tetrone (NP0280034)

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Record Information

Version

2.0

Created at

2022-09-09 05:37:49 UTC

Updated at

2022-09-09 05:37:49 UTC

NP-MRD ID

NP0280034

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1s,3r,12r,15r,16s,18r)-11,11,15-trimethyl-1,16,18-tris(3-methylbut-2-en-1-yl)-20-oxapentacyclo[16.2.1.0³,¹².0³,¹⁵.0⁵,¹⁰]henicosa-5,7,9-triene-2,4,19,21-tetrone

Description

Hyphenrone D belongs to the class of organic compounds known as terpene lactones. These are prenol lipids containing a lactone ring. (1s,3r,12r,15r,16s,18r)-11,11,15-trimethyl-1,16,18-tris(3-methylbut-2-en-1-yl)-20-oxapentacyclo[16.2.1.0³,¹².0³,¹⁵.0⁵,¹⁰]henicosa-5,7,9-triene-2,4,19,21-tetrone is found in Hypericum henryi. Based on a literature review very few articles have been published on Hyphenrone D.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309092207372D          

 43 47  0  0  1  0            999 V2000
    4.7248    1.8739    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9275    1.6621    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3454    2.2467    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7123    0.8657    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9149    0.6538    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6997   -0.1426    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.3621   -0.6743    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4975   -1.5331    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.3090   -1.3844    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5859   -0.6072    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3974   -0.4585    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6743    0.3186    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9319   -1.0869    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6760   -2.3866    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4351   -2.7097    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9385   -2.8487    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2594   -2.3118    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.7421   -2.9544    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0400   -3.7238    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8552   -3.8505    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1530   -4.6198    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3725   -3.2079    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8192   -1.8256    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3802   -1.1271    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5870   -1.7606    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9232   -2.2505    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2446   -0.9211    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
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    0.6856   -2.5148    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0867   -1.9738    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1330   -2.7690    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9315   -2.9764    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5103   -2.3885    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2907   -1.5933    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.2780   -0.5865    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0992   -0.5079    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3364    0.2364    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5405   -0.3886    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.6962    0.4295    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5143    0.5035    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8483   -0.2700    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.2491    0.4511    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
  2  4  2  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  0  0  0  0
  8  9  1  6  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 11 13  1  0  0  0  0
  8 14  1  0  0  0  0
 14 15  2  0  0  0  0
 14 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  6  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 20 21  1  0  0  0  0
 20 22  1  0  0  0  0
 17 23  1  0  0  0  0
  8 23  1  0  0  0  0
 23 24  2  0  0  0  0
 17 25  1  0  0  0  0
 25 26  2  0  0  0  0
 25 27  1  0  0  0  0
 27 28  1  1  0  0  0
 28 29  2  0  0  0  0
 28 30  1  0  0  0  0
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 31 32  1  0  0  0  0
 32 33  2  0  0  0  0
 33 34  1  0  0  0  0
 34 35  2  0  0  0  0
 30 35  1  0  0  0  0
 35 36  1  0  0  0  0
 36 37  1  0  0  0  0
 36 38  1  0  0  0  0
 36 39  1  0  0  0  0
 27 39  1  0  0  0  0
 39 40  1  1  0  0  0
 40 41  1  0  0  0  0
 41 42  1  0  0  0  0
  6 42  1  0  0  0  0
 27 42  1  0  0  0  0
 42 43  1  1  0  0  0
M  END

     RDKit          3D

 91 95  0  0  0  0  0  0  0  0999 V2000
    5.0961    3.0222   -2.7660 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2340    2.2638   -1.7247 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5814    2.5838   -0.3517 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3620    1.4088   -2.1425 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3676    0.5033   -1.5904 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8823    0.6181   -0.2018 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.2052    1.9005    0.0356 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1823    2.2141   -0.2672 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.4637    3.6645   -0.0417 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3482    4.3804    1.1666 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0856    4.2858    2.4120 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1406    5.5857    3.2546 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2579    3.1099    3.2133 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4280    2.1327   -1.7903 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0984    2.9345   -2.5821 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -4.8638    0.7569   -3.0424 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2909    1.4116    0.1990 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9981    1.4292    1.1941 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.5146   -1.1909   -1.9519 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3666   -1.4371    0.1734 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.6197   -2.7341   -0.5058 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5892   -2.9919   -1.2423 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3310   -3.8131   -0.3137 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6818   -4.7008   -1.3410 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5940   -5.7184   -1.1646 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1875   -5.8729    0.0708 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8611   -5.0105    1.1090 C   0  0  0  0  0  0  0  0  0  0  0  0
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    4.7901    2.7451   -3.7720 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9588    4.0886   -2.5053 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.1154    3.2294    4.2652 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3833    2.9934    3.2453 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5511    0.9074   -1.0307 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.7082   -1.9318    3.4322 H   0  0  0  0  0  0  0  0  0  0  0  0
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    1.5511    0.7719    2.2099 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3615   -0.7250    2.5740 H   0  0  0  0  0  0  0  0  0  0  0  0
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    3.3444   -1.4739   -0.4612 H   0  0  0  0  0  0  0  0  0  0  0  0
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 32 75  1  0
 31 74  1  0
M  END


  Mrv1652309092207372D          

 43 47  0  0  1  0            999 V2000
    4.7248    1.8739    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9275    1.6621    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3454    2.2467    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    2.9149    0.6538    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6997   -0.1426    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.3621   -0.6743    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4975   -1.5331    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.3090   -1.3844    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5859   -0.6072    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3974   -0.4585    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6743    0.3186    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9319   -1.0869    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6760   -2.3866    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4351   -2.7097    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9385   -2.8487    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2594   -2.3118    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.7421   -2.9544    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0400   -3.7238    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8552   -3.8505    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1530   -4.6198    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3725   -3.2079    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8192   -1.8256    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3802   -1.1271    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5870   -1.7606    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9232   -2.2505    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2446   -0.9211    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.8641   -1.7093    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6856   -2.5148    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0867   -1.9738    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1330   -2.7690    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9315   -2.9764    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5103   -2.3885    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2907   -1.5933    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4922   -1.3859    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2780   -0.5865    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0992   -0.5079    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3364    0.2364    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5405   -0.3886    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.6962    0.4295    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5143    0.5035    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8483   -0.2700    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.2491    0.4511    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
  2  4  2  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  0  0  0  0
  8  9  1  6  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 11 13  1  0  0  0  0
  8 14  1  0  0  0  0
 14 15  2  0  0  0  0
 14 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  6  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 20 21  1  0  0  0  0
 20 22  1  0  0  0  0
 17 23  1  0  0  0  0
  8 23  1  0  0  0  0
 23 24  2  0  0  0  0
 17 25  1  0  0  0  0
 25 26  2  0  0  0  0
 25 27  1  0  0  0  0
 27 28  1  1  0  0  0
 28 29  2  0  0  0  0
 28 30  1  0  0  0  0
 30 31  2  0  0  0  0
 31 32  1  0  0  0  0
 32 33  2  0  0  0  0
 33 34  1  0  0  0  0
 34 35  2  0  0  0  0
 30 35  1  0  0  0  0
 35 36  1  0  0  0  0
 36 37  1  0  0  0  0
 36 38  1  0  0  0  0
 36 39  1  0  0  0  0
 27 39  1  0  0  0  0
 39 40  1  1  0  0  0
 40 41  1  0  0  0  0
 41 42  1  0  0  0  0
  6 42  1  0  0  0  0
 27 42  1  0  0  0  0
 42 43  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0280034

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)=CC[C@H]1C[C@@]2(CC=C(C)C)C(=O)O[C@](CC=C(C)C)(C2=O)C(=O)[C@]23[C@H](CC[C@]12C)C(C)(C)C1=CC=CC=C1C3=O

> <INCHI_IDENTIFIER>
InChI=1S/C38H48O5/c1-23(2)14-15-26-22-36(20-16-24(3)4)31(40)37(43-33(36)42,21-17-25(5)6)32(41)38-29(18-19-35(26,38)9)34(7,8)28-13-11-10-12-27(28)30(38)39/h10-14,16-17,26,29H,15,18-22H2,1-9H3/t26-,29+,35+,36+,37+,38+/m0/s1

> <INCHI_KEY>
FPHBKYRPWQOBBF-PPXCZVBLSA-N

> <FORMULA>
C38H48O5

> <MOLECULAR_WEIGHT>
584.797

> <EXACT_MASS>
584.350174646

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
91

> <JCHEM_AVERAGE_POLARIZABILITY>
66.16183724203248

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1S,3R,12R,15R,16S,18R)-11,11,15-trimethyl-1,16,18-tris(3-methylbut-2-en-1-yl)-20-oxapentacyclo[16.2.1.0^{3,12}.0^{3,15}.0^{5,10}]henicosa-5,7,9-triene-2,4,19,21-tetrone

> <JCHEM_LOGP>
9.485282960333333

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-7.096672601612776

> <JCHEM_POLAR_SURFACE_AREA>
77.51

> <JCHEM_REFRACTIVITY>
172.21359999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(1S,3R,12R,15R,16S,18R)-11,11,15-trimethyl-1,16,18-tris(3-methylbut-2-en-1-yl)-20-oxapentacyclo[16.2.1.0^{3,12}.0^{3,15}.0^{5,10}]henicosa-5,7,9-triene-2,4,19,21-tetrone

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 09-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   09-SEP-22         0                                  
HETATM    1  C   UNK     0       8.820   3.498   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       7.331   3.103   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       6.245   4.194   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       6.930   1.616   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       5.441   1.221   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       5.039  -0.266   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.276  -1.259   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       6.529  -2.862   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       8.043  -2.584   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       8.560  -1.133   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      10.075  -0.856   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      10.592   0.595   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      11.073  -2.029   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       6.862  -4.455   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       8.279  -5.058   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0       5.485  -5.317   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       4.218  -4.315   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       3.252  -5.515   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       3.808  -6.951   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       5.330  -7.188   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       5.886  -8.624   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       6.295  -5.988   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       5.263  -3.408   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       4.443  -2.104   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       2.962  -3.286   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0       1.723  -4.201   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0       2.323  -1.719   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       1.613  -3.191   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0       1.280  -4.694   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0       0.162  -3.684   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      -0.248  -5.169   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      -1.739  -5.556   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      -2.819  -4.459   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      -2.409  -2.974   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      -0.919  -2.587   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      -0.519  -1.095   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0      -2.052  -0.948   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0      -0.628   0.441   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0       1.009  -0.725   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0       1.300   0.802   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0       2.827   0.940   0.000  0.00  0.00           C+0
HETATM   42  C   UNK     0       3.450  -0.504   0.000  0.00  0.00           C+0
HETATM   43  C   UNK     0       4.198   0.842   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7   42                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   14   23                                             
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11                                                            
CONECT   14    8   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14   17                                                       
CONECT   17   16   18   23   25                                             
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20                                                            
CONECT   23   17    8   24                                                  
CONECT   24   23                                                            
CONECT   25   17   26   27                                                  
CONECT   26   25                                                            
CONECT   27   25   28   39   42                                             
CONECT   28   27   29   30                                                  
CONECT   29   28                                                            
CONECT   30   28   31   35                                                  
CONECT   31   30   32                                                       
CONECT   32   31   33                                                       
CONECT   33   32   34                                                       
CONECT   34   33   35                                                       
CONECT   35   34   30   36                                                  
CONECT   36   35   37   38   39                                             
CONECT   37   36                                                            
CONECT   38   36                                                            
CONECT   39   36   27   40                                                  
CONECT   40   39   41                                                       
CONECT   41   40   42                                                       
CONECT   42   41    6   27   43                                             
CONECT   43   42                                                            
MASTER        0    0    0    0    0    0    0    0   43    0   94    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₃₈H₄₈O₅

Average Mass

584.7970 Da

Monoisotopic Mass

584.35017 Da

IUPAC Name

(1S,3R,12R,15R,16S,18R)-11,11,15-trimethyl-1,16,18-tris(3-methylbut-2-en-1-yl)-20-oxapentacyclo[16.2.1.0^{3,12}.0^{3,15}.0^{5,10}]henicosa-5,7,9-triene-2,4,19,21-tetrone

Traditional Name

(1S,3R,12R,15R,16S,18R)-11,11,15-trimethyl-1,16,18-tris(3-methylbut-2-en-1-yl)-20-oxapentacyclo[16.2.1.0^{3,12}.0^{3,15}.0^{5,10}]henicosa-5,7,9-triene-2,4,19,21-tetrone

CAS Registry Number

Not Available

SMILES

CC(C)=CC[C@H]1C[C@@]2(CC=C(C)C)C(=O)O[C@](CC=C(C)C)(C2=O)C(=O)[C@]23[C@H](CC[C@]12C)C(C)(C)C1=CC=CC=C1C3=O

InChI Identifier

InChI=1S/C38H48O5/c1-23(2)14-15-26-22-36(20-16-24(3)4)31(40)37(43-33(36)42,21-17-25(5)6)32(41)38-29(18-19-35(26,38)9)34(7,8)28-13-11-10-12-27(28)30(38)39/h10-14,16-17,26,29H,15,18-22H2,1-9H3/t26-,29+,35+,36+,37+,38+/m0/s1

InChI Key

FPHBKYRPWQOBBF-PPXCZVBLSA-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
Hypericum henryi	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as terpene lactones. These are prenol lipids containing a lactone ring.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Terpene lactones

Direct Parent

Terpene lactones

Alternative Parents

Substituents

Terpene lactone
Aromatic monoterpenoid
Monoterpenoid
Tetralin
Aryl ketone
Aryl alkyl ketone
Alpha-acyloxy ketone
3-furanone
Gamma butyrolactone
Benzenoid
Oxolane
Lactone
Ketone
Carboxylic acid ester
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Oxacycle
Organoheterocyclic compound
Hydrocarbon derivative
Organooxygen compound
Organic oxide
Organic oxygen 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
logP	9.49	ChemAxon
pKa (Strongest Basic)	-7.1	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	77.51 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	172.21 m³·mol⁻¹	ChemAxon
Polarizability	66.16 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

34485483

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

102129929

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (1s,3r,12r,15r,16s,18r)-11,11,15-trimethyl-1,16,18-tris(3-methylbut-2-en-1-yl)-20-oxapentacyclo[16.2.1.0³,¹².0³,¹⁵.0⁵,¹⁰]henicosa-5,7,9-triene-2,4,19,21-tetrone (NP0280034)

MOL for NP0280034 ((1s,3r,12r,15r,16s,18r)-11,11,15-trimethyl-1,16,18-tris(3-methylbut-2-en-1-yl)-20-oxapentacyclo[16.2.1.0³,¹².0³,¹⁵.0⁵,¹⁰]henicosa-5,7,9-triene-2,4,19,21-tetrone)

3D MOL for NP0280034 ((1s,3r,12r,15r,16s,18r)-11,11,15-trimethyl-1,16,18-tris(3-methylbut-2-en-1-yl)-20-oxapentacyclo[16.2.1.0³,¹².0³,¹⁵.0⁵,¹⁰]henicosa-5,7,9-triene-2,4,19,21-tetrone)

3D SDF for NP0280034 ((1s,3r,12r,15r,16s,18r)-11,11,15-trimethyl-1,16,18-tris(3-methylbut-2-en-1-yl)-20-oxapentacyclo[16.2.1.0³,¹².0³,¹⁵.0⁵,¹⁰]henicosa-5,7,9-triene-2,4,19,21-tetrone)

3D-SDF for NP0280034 ((1s,3r,12r,15r,16s,18r)-11,11,15-trimethyl-1,16,18-tris(3-methylbut-2-en-1-yl)-20-oxapentacyclo[16.2.1.0³,¹².0³,¹⁵.0⁵,¹⁰]henicosa-5,7,9-triene-2,4,19,21-tetrone)

PDB for NP0280034 ((1s,3r,12r,15r,16s,18r)-11,11,15-trimethyl-1,16,18-tris(3-methylbut-2-en-1-yl)-20-oxapentacyclo[16.2.1.0³,¹².0³,¹⁵.0⁵,¹⁰]henicosa-5,7,9-triene-2,4,19,21-tetrone)

3D PDB for NP0280034 ((1s,3r,12r,15r,16s,18r)-11,11,15-trimethyl-1,16,18-tris(3-methylbut-2-en-1-yl)-20-oxapentacyclo[16.2.1.0³,¹².0³,¹⁵.0⁵,¹⁰]henicosa-5,7,9-triene-2,4,19,21-tetrone)

SMILES for NP0280034 ((1s,3r,12r,15r,16s,18r)-11,11,15-trimethyl-1,16,18-tris(3-methylbut-2-en-1-yl)-20-oxapentacyclo[16.2.1.0³,¹².0³,¹⁵.0⁵,¹⁰]henicosa-5,7,9-triene-2,4,19,21-tetrone)

INCHI for NP0280034 ((1s,3r,12r,15r,16s,18r)-11,11,15-trimethyl-1,16,18-tris(3-methylbut-2-en-1-yl)-20-oxapentacyclo[16.2.1.0³,¹².0³,¹⁵.0⁵,¹⁰]henicosa-5,7,9-triene-2,4,19,21-tetrone)

Structure for NP0280034 ((1s,3r,12r,15r,16s,18r)-11,11,15-trimethyl-1,16,18-tris(3-methylbut-2-en-1-yl)-20-oxapentacyclo[16.2.1.0³,¹².0³,¹⁵.0⁵,¹⁰]henicosa-5,7,9-triene-2,4,19,21-tetrone)

3D Structure for NP0280034 ((1s,3r,12r,15r,16s,18r)-11,11,15-trimethyl-1,16,18-tris(3-methylbut-2-en-1-yl)-20-oxapentacyclo[16.2.1.0³,¹².0³,¹⁵.0⁵,¹⁰]henicosa-5,7,9-triene-2,4,19,21-tetrone)