NP-MRD: Showing NP-Card for 8beta-Hydroxyproustianol angelicate (NP0064706)

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Record Information

Version

2.0

Created at

2022-04-28 08:53:51 UTC

Updated at

2022-04-28 08:53:51 UTC

NP-MRD ID

NP0064706

Secondary Accession Numbers

None

Natural Product Identification

Common Name

8beta-Hydroxyproustianol angelicate

Description

(1R,2R,5S,7S,8S,9R,11S,12S)-5,7-bis(acetyloxy)-9-hydroxy-14,14-dimethyl-6-oxatetracyclo[9.2.1.0⁴,¹².0⁸,¹²]Tetradec-3-en-2-yl (2Z)-2-methylbut-2-enoate belongs to the class of organic compounds known as cedrane and isocedrane sesquiterpenoids. These are sesquiternoids with a structure based on the cedrane or the isocedrane skeleton. Cedrane is a tricyclic molecules a 3,6,8,8-tetramethyl-1H-3a,7-methano-azulene moiety. Isocedrane is a rearranged cedrane arising from the migration of methyl group moved from the 6-position to the 4-position. 8beta-Hydroxyproustianol angelicate is found in Proustia pyrifolia. Based on a literature review very few articles have been published on (1R,2R,5S,7S,8S,9R,11S,12S)-5,7-bis(acetyloxy)-9-hydroxy-14,14-dimethyl-6-oxatetracyclo[9.2.1.0⁴,¹².0⁸,¹²]Tetradec-3-en-2-yl (2Z)-2-methylbut-2-enoate.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304282210532D          

 32 35  0  0  1  0            999 V2000
    0.3329    0.0347    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1538   -0.0615    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.5280    0.6968    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.9606    1.3332    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.1982    0.8424    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.5198    1.3272    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2632    2.1403    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.4059    1.7636    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1410    2.8969    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.9892    2.9248    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3695    2.1421    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1845    2.2633    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.6733    1.6099    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3541    0.8428    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.8701    0.1991    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6856    0.3241    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2016   -0.3197    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9851    1.0928    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4986    3.0262    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9949    3.6796    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1772    3.5701    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3089    4.4425    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2948    3.5974    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1194    3.5703    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5081    2.8427    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5551    4.2708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3797    4.2437    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7685    3.5161    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1663    4.9985    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0631    0.7064    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3314    1.4753    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5478   -0.7864    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  3  2  1  6  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  1  1  1  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  1  0  0  0
  4  8  1  1  0  0  0
  7  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
  4 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
  3 14  1  0  0  0  0
 14 15  1  1  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 16 18  1  0  0  0  0
 12 19  1  6  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 20 22  1  0  0  0  0
  9 23  1  6  0  0  0
 23 24  1  0  0  0  0
 24 25  2  0  0  0  0
 24 26  1  0  0  0  0
 26 27  2  0  0  0  0
 27 28  1  0  0  0  0
 26 29  1  0  0  0  0
  6 30  1  0  0  0  0
  6 31  1  0  0  0  0
  2 32  1  6  0  0  0
M  END

     RDKit          3D

 64 67  0  0  0  0  0  0  0  0999 V2000
   -5.0288    0.0484   -0.8414 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6852    0.9696    0.0985 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0303    1.5479    1.0857 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7967    2.4588    1.9719 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6276    1.3230    1.3143 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0500    1.9080    2.2826 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8168    0.5035    0.5561 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4599    0.3044    0.7972 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.5667    0.8985   -0.2555 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6976    0.5135   -0.3378 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7904    1.3455   -0.8529 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.3950    2.5371   -1.4507 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7519    3.7971   -1.0446 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2253    4.9616   -1.8164 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4924    3.9245   -0.0600 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5684    0.5308   -1.6801 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2784   -0.3316   -0.8812 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.2784    0.4287   -0.2096 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6267    0.2537   -0.4495 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6197    1.0793    0.2847 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0244   -0.5821   -1.2686 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4742   -1.1867    0.0410 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.5416   -2.6618   -0.3129 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.4098   -2.8978   -1.3788 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1612   -3.0856   -0.7494 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2706   -1.8980   -0.6718 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.0076   -2.0789    0.0656 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.1632   -2.0273   -0.9011 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0976   -3.4569    0.7375 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0425   -1.0792    1.1590 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.4541   -0.9907    1.5262 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0315   -0.8601    0.1222 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.7456   -0.1790   -1.6694 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7412   -0.8945   -0.3298 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1817    0.5638   -1.3131 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7547    1.1691   -0.0415 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4287    3.1468    1.3534 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1463    3.0535    2.6179 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5225    1.8307    2.5418 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2229    0.9377    1.7119 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9247    1.6307   -0.9440 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4519    1.6164    0.0178 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5827    4.6351   -2.6502 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0422    5.5699   -2.2225 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6039    5.6325   -1.1774 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8268   -1.0312   -1.5784 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2744    2.1257    0.4341 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7802    0.5608    1.2686 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5769    1.0887   -0.2790 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9044   -1.0194    1.0741 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8513   -3.2179    0.6000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9487   -3.7279   -1.1953 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8030   -3.9791   -0.1890 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1572   -3.4241   -1.8279 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0563   -1.4622   -1.6903 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8134   -2.5775   -1.8245 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3561   -0.9925   -1.2496 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0391   -2.5691   -0.5471 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0656   -3.4618    1.3195 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2126   -4.2132   -0.0377 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3115   -3.6176    1.4747 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5387   -1.4422    2.0866 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6365   -0.0574    2.1020 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7906   -1.8919    2.0388 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  3  5  1  0
  5  6  2  0
  5  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 13 15  2  0
 11 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 19 21  2  0
 17 22  1  0
 22 23  1  0
 23 24  1  0
 23 25  1  0
 25 26  1  0
 26 27  1  0
 27 28  1  6
 27 29  1  0
 27 30  1  0
 30 31  1  0
 32 31  1  1
 30  8  1  0
 32 10  1  0
 32 22  1  0
 32 26  1  0
  1 33  1  0
  1 34  1  0
  1 35  1  0
  2 36  1  0
  4 37  1  0
  4 38  1  0
  4 39  1  0
  8 40  1  1
  9 41  1  0
 11 42  1  1
 14 43  1  0
 14 44  1  0
 14 45  1  0
 17 46  1  6
 20 47  1  0
 20 48  1  0
 20 49  1  0
 22 50  1  1
 23 51  1  1
 24 52  1  0
 25 53  1  0
 25 54  1  0
 26 55  1  6
 28 56  1  0
 28 57  1  0
 28 58  1  0
 29 59  1  0
 29 60  1  0
 29 61  1  0
 30 62  1  1
 31 63  1  0
 31 64  1  0
M  END


  Mrv1652304282210532D          

 32 35  0  0  1  0            999 V2000
    0.3329    0.0347    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1538   -0.0615    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.5280    0.6968    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.9606    1.3332    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.1982    0.8424    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.5198    1.3272    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2632    2.1403    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.4059    1.7636    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1410    2.8969    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.9892    2.9248    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3695    2.1421    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1845    2.2633    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.6733    1.6099    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3541    0.8428    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.8701    0.1991    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6856    0.3241    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2016   -0.3197    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9851    1.0928    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4986    3.0262    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9949    3.6796    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1772    3.5701    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3089    4.4425    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2948    3.5974    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1194    3.5703    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5081    2.8427    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5551    4.2708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3797    4.2437    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7685    3.5161    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1663    4.9985    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0631    0.7064    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3314    1.4753    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5478   -0.7864    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  3  2  1  6  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  1  1  1  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  1  0  0  0
  4  8  1  1  0  0  0
  7  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
  4 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
  3 14  1  0  0  0  0
 14 15  1  1  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 16 18  1  0  0  0  0
 12 19  1  6  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 20 22  1  0  0  0  0
  9 23  1  6  0  0  0
 23 24  1  0  0  0  0
 24 25  2  0  0  0  0
 24 26  1  0  0  0  0
 26 27  2  0  0  0  0
 27 28  1  0  0  0  0
 26 29  1  0  0  0  0
  6 30  1  0  0  0  0
  6 31  1  0  0  0  0
  2 32  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0064706

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C\C=C(\C)C(=O)O[C@@H]1C=C2[C@H](OC(C)=O)O[C@@H](OC(C)=O)[C@@H]3[C@H](O)C[C@H]4C(C)(C)[C@H]1C[C@@]234

> <INCHI_IDENTIFIER>
InChI=1S/C24H32O8/c1-7-11(2)20(28)31-17-8-14-21(29-12(3)25)32-22(30-13(4)26)19-16(27)9-18-23(5,6)15(17)10-24(14,18)19/h7-8,15-19,21-22,27H,9-10H2,1-6H3/b11-7-/t15-,16+,17+,18-,19-,21+,22+,24-/m0/s1

> <INCHI_KEY>
GKBCYQZLYMMXKN-XQSDFSHVSA-N

> <FORMULA>
C24H32O8

> <MOLECULAR_WEIGHT>
448.512

> <EXACT_MASS>
448.20971799

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
64

> <JCHEM_AVERAGE_POLARIZABILITY>
47.116688864078284

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1R,2R,5S,7S,8S,9R,11S,12S)-5,7-bis(acetyloxy)-9-hydroxy-14,14-dimethyl-6-oxatetracyclo[9.2.1.0^{4,12}.0^{8,12}]tetradec-3-en-2-yl (2Z)-2-methylbut-2-enoate

> <ALOGPS_LOGP>
1.99

> <JCHEM_LOGP>
2.597258441333333

> <ALOGPS_LOGS>
-3.58

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.749524906572628

> <JCHEM_PKA_STRONGEST_BASIC>
-2.9083578058651325

> <JCHEM_POLAR_SURFACE_AREA>
108.36

> <JCHEM_REFRACTIVITY>
112.8057

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.18e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1R,2R,5S,7S,8S,9R,11S,12S)-5,7-bis(acetyloxy)-9-hydroxy-14,14-dimethyl-6-oxatetracyclo[9.2.1.0^{4,12}.0^{8,12}]tetradec-3-en-2-yl (2Z)-2-methylbut-2-enoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 28-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   28-APR-22         0                                  
HETATM    1  C   UNK     0       0.621   0.065   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.154  -0.115   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.852   1.301   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.793   2.489   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.370   1.572   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -0.970   2.477   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -0.491   3.995   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.758   3.292   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.263   5.408   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.847   5.460   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.556   3.999   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.078   4.225   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       4.990   3.005   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       4.394   1.573   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       5.358   0.372   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       6.880   0.605   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       7.843  -0.597   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       7.439   2.040   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       4.664   5.649   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       3.724   6.869   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       2.197   6.664   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       4.310   8.293   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0      -0.550   6.715   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0      -2.089   6.665   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0      -2.815   5.306   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0      -2.903   7.972   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      -4.442   7.922   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      -5.168   6.563   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      -2.177   9.330   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      -1.985   1.319   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      -2.485   2.754   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0       2.889  -1.468   0.000  0.00  0.00           O+0
CONECT    1    2    5                                                       
CONECT    2    1    3   32                                                  
CONECT    3    2    4   14                                                  
CONECT    4    3    5    8   11                                             
CONECT    5    4    1    6                                                  
CONECT    6    5    7   30   31                                             
CONECT    7    6    8    9                                                  
CONECT    8    7    4                                                       
CONECT    9    7   10   23                                                  
CONECT   10    9   11                                                       
CONECT   11   10    4   12                                                  
CONECT   12   11   13   19                                                  
CONECT   13   12   14                                                       
CONECT   14   13    3   15                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16                                                            
CONECT   19   12   20                                                       
CONECT   20   19   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20                                                            
CONECT   23    9   24                                                       
CONECT   24   23   25   26                                                  
CONECT   25   24                                                            
CONECT   26   24   27   29                                                  
CONECT   27   26   28                                                       
CONECT   28   27                                                            
CONECT   29   26                                                            
CONECT   30    6                                                            
CONECT   31    6                                                            
CONECT   32    2                                                            
MASTER        0    0    0    0    0    0    0    0   32    0   70    0
END

View in JSmol

Synonyms

Value	Source
(1R,2R,5S,7S,8S,9R,11S,12S)-5,7-Bis(acetyloxy)-9-hydroxy-14,14-dimethyl-6-oxatetracyclo[9.2.1.0,.0,]tetradec-3-en-2-yl (2Z)-2-methylbut-2-enoic acid	Generator

Chemical Formula

C₂₄H₃₂O₈

Average Mass

448.5120 Da

Monoisotopic Mass

448.20972 Da

IUPAC Name

(1R,2R,5S,7S,8S,9R,11S,12S)-5,7-bis(acetyloxy)-9-hydroxy-14,14-dimethyl-6-oxatetracyclo[9.2.1.0^{4,12}.0^{8,12}]tetradec-3-en-2-yl (2Z)-2-methylbut-2-enoate

Traditional Name

(1R,2R,5S,7S,8S,9R,11S,12S)-5,7-bis(acetyloxy)-9-hydroxy-14,14-dimethyl-6-oxatetracyclo[9.2.1.0^{4,12}.0^{8,12}]tetradec-3-en-2-yl (2Z)-2-methylbut-2-enoate

CAS Registry Number

Not Available

SMILES

C\C=C(\C)C(=O)O[C@@H]1C=C2[C@H](OC(C)=O)O[C@@H](OC(C)=O)[C@@H]3[C@H](O)C[C@H]4C(C)(C)[C@H]1C[C@@]234

InChI Identifier

InChI=1S/C24H32O8/c1-7-11(2)20(28)31-17-8-14-21(29-12(3)25)32-22(30-13(4)26)19-16(27)9-18-23(5,6)15(17)10-24(14,18)19/h7-8,15-19,21-22,27H,9-10H2,1-6H3/b11-7-/t15-,16+,17+,18-,19-,21+,22+,24-/m0/s1

InChI Key

GKBCYQZLYMMXKN-XQSDFSHVSA-N

Experimental Spectra

Not Available

Predicted Spectra

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

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Proustia pyrifolia	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as cedrane and isocedrane sesquiterpenoids. These are sesquiternoids with a structure based on the cedrane or the isocedrane skeleton. Cedrane is a tricyclic molecules a 3,6,8,8-tetramethyl-1H-3a,7-methano-azulene moiety. Isocedrane is a rearranged cedrane arising from the migration of methyl group moved from the 6-position to the 4-position.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Sesquiterpenoids

Direct Parent

Cedrane and isocedrane sesquiterpenoids

Alternative Parents

Substituents

Isocedrane sesquiterpenoid
Tricarboxylic acid or derivatives
Fatty acid ester
Fatty acyl
Oxane
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Cyclic alcohol
Secondary alcohol
Carboxylic acid ester
Oxacycle
Organoheterocyclic compound
Carboxylic acid derivative
Acetal
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Alcohol
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	1.99	ALOGPS
logP	2.6	ChemAxon
logS	-3.6	ALOGPS
pKa (Strongest Acidic)	14.75	ChemAxon
pKa (Strongest Basic)	-2.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	108.36 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	112.81 m³·mol⁻¹	ChemAxon
Polarizability	47.12 Å³	ChemAxon
Number of Rings	4	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

Not Available

Chemspider ID

10289733

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

21676087

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for 8beta-Hydroxyproustianol angelicate (NP0064706)

MOL for NP0064706 (8beta-Hydroxyproustianol angelicate)

3D MOL for NP0064706 (8beta-Hydroxyproustianol angelicate)

3D SDF for NP0064706 (8beta-Hydroxyproustianol angelicate)

3D-SDF for NP0064706 (8beta-Hydroxyproustianol angelicate)

PDB for NP0064706 (8beta-Hydroxyproustianol angelicate)

3D PDB for NP0064706 (8beta-Hydroxyproustianol angelicate)

SMILES for NP0064706 (8beta-Hydroxyproustianol angelicate)

INCHI for NP0064706 (8beta-Hydroxyproustianol angelicate)

Structure for NP0064706 (8beta-Hydroxyproustianol angelicate)

3D Structure for NP0064706 (8beta-Hydroxyproustianol angelicate)