NP-MRD: Showing NP-Card for (2s,4s,5as,6s,8r,8as)-6-acetyl-6-benzoyl-8-hydroxy-8a-(2-hydroxypropan-2-yl)-2,8-dimethyl-7-oxo-tetrahydro-2h-cyclopenta[b]oxepine-4-carboxylic acid (NP0158285)

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Record Information

Version

2.0

Created at

2022-09-02 15:50:53 UTC

Updated at

2022-09-02 15:50:53 UTC

NP-MRD ID

NP0158285

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(2s,4s,5as,6s,8r,8as)-6-acetyl-6-benzoyl-8-hydroxy-8a-(2-hydroxypropan-2-yl)-2,8-dimethyl-7-oxo-tetrahydro-2h-cyclopenta[b]oxepine-4-carboxylic acid

Description

Hypertricone belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units. (2s,4s,5as,6s,8r,8as)-6-acetyl-6-benzoyl-8-hydroxy-8a-(2-hydroxypropan-2-yl)-2,8-dimethyl-7-oxo-tetrahydro-2h-cyclopenta[b]oxepine-4-carboxylic acid is found in Hypericum geminiflorum. Based on a literature review very few articles have been published on Hypertricone.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309022217502D          

 32 34  0  0  1  0            999 V2000
    1.0547   -3.4008    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0825   -2.5258    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8896   -2.4648    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9566   -1.6436    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.2150   -2.1502    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1564   -2.9363    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4723   -1.6436    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2235   -1.9847    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8945   -1.5047    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8143   -0.6836    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0631   -0.3425    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0958   -0.6362    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4717   -0.9761    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3505   -1.1000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9566   -0.3087    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.5385    0.6773    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2057    0.6199    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7413   -0.5636    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.6661    0.3853    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1967    1.2611    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3795    0.9585    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7414    0.1918    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3863   -0.0492    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1906   -0.2328    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.9834    0.1399    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5485   -0.9761    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1906   -1.7194    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.8807   -2.3090    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9741   -3.1678    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7412   -2.3407    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3863   -1.9030    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7413   -1.3886    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  4  2  1  1  0  0  0
  4  5  1  6  0  0  0
  5  6  2  0  0  0  0
  5  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
  7 12  1  0  0  0  0
  4 13  1  0  0  0  0
 13 14  2  0  0  0  0
 13 15  1  0  0  0  0
 15 16  1  1  0  0  0
 15 17  1  6  0  0  0
 15 18  1  0  0  0  0
 18 19  1  1  0  0  0
 19 20  1  0  0  0  0
 19 21  1  0  0  0  0
 19 22  1  0  0  0  0
 18 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  1  0  0  0
 24 26  1  0  0  0  0
 26 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
 27 31  1  0  0  0  0
 32 31  1  1  0  0  0
  4 32  1  0  0  0  0
 18 32  1  0  0  0  0
M  END

     RDKit          3D

 62 64  0  0  0  0  0  0  0  0999 V2000
    2.0145   -2.1116    1.3333 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9446   -0.6520    1.1974 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6242   -0.0080    2.0053 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1497    0.0485    0.2114 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.7003    1.4556    0.1380 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9104    2.4358    0.2905 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0799    1.7327   -0.0972 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4909    3.0725   -0.1718 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7749    3.4730   -0.3861 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7653    2.5226   -0.5451 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4125    1.1964   -0.4801 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0835    0.8158   -0.2584 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2483   -0.4395   -1.1924 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0828   -0.9689   -1.8600 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1000   -0.1160   -1.7674 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.3120   -0.5923   -3.1303 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1026    1.3054   -1.8244 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0637   -0.4781   -0.6889 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.5727   -1.8670   -0.6336 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6587   -3.0184   -0.7054 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5226   -2.0886   -1.8514 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4666   -2.0792    0.4238 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2036    0.3048   -0.9593 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6387    1.1898   -0.0655 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.0180    1.6396   -0.6853 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9950    0.7928    1.3080 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9641    0.4674    2.2961 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.6012   -0.3158    3.3913 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8170   -0.6264    3.4292 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8081   -0.7365    4.4471 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7523   -0.2988    1.8255 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3204    0.0544    0.4710 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.9576   -2.4416    1.8600 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9913   -2.6428    0.3502 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1554   -2.4812    1.9222 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7462    3.8491   -0.0527 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0846    4.5010   -0.4425 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8008    2.8266   -0.7179 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1819    0.4179   -0.6034 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9165   -0.2580   -0.2218 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0734   -1.6102   -3.3695 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3362   -0.3959   -3.4985 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3174    0.0500   -3.8316 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4213    1.5951   -2.5976 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2691   -2.8865   -1.2558 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2198   -3.9453   -1.0678 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3702   -3.3491    0.3181 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9995   -2.5353   -2.6962 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0833   -1.1895   -2.0943 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3097   -2.8560   -1.5771 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3694   -2.9839    0.8128 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1379    2.1879   -0.0196 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5826    2.1976    0.0880 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8362    2.3021   -1.5303 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5936    0.7241   -0.9261 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5576    1.7033    1.7347 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8348    0.0295    1.3593 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6296    1.4248    2.7998 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0443   -0.1641    4.8137 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9062   -1.3727    2.0516 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0689   -0.0030    2.5067 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5379    1.1962    0.4203 H   0  0  0  0  0  0  0  0  0  0  0  0
 25 24  1  0
 24 26  1  0
 26 27  1  0
 27 31  1  0
 31 32  1  0
 32  4  1  0
  4  2  1  1
  2  1  1  0
  2  3  2  0
  4  5  1  0
  5  6  2  0
  5  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
  4 13  1  0
 13 14  2  0
 13 15  1  0
 15 16  1  0
 15 17  1  6
 15 18  1  0
 18 23  1  0
 18 19  1  1
 19 20  1  0
 19 21  1  0
 19 22  1  0
 27 28  1  0
 28 30  1  0
 28 29  2  0
 23 24  1  0
 18 32  1  0
 12  7  1  0
 25 53  1  0
 25 54  1  0
 25 55  1  0
 24 52  1  1
 26 56  1  0
 26 57  1  0
 27 58  1  1
 31 60  1  0
 31 61  1  0
 32 62  1  1
  1 33  1  0
  1 34  1  0
  1 35  1  0
  8 36  1  0
  9 37  1  0
 10 38  1  0
 11 39  1  0
 12 40  1  0
 16 41  1  0
 16 42  1  0
 16 43  1  0
 17 44  1  0
 20 45  1  0
 20 46  1  0
 20 47  1  0
 21 48  1  0
 21 49  1  0
 21 50  1  0
 22 51  1  0
 30 59  1  0
M  END


  Mrv1652309022217502D          

 32 34  0  0  1  0            999 V2000
    1.0547   -3.4008    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0825   -2.5258    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8896   -2.4648    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9566   -1.6436    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.2150   -2.1502    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1564   -2.9363    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4723   -1.6436    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2235   -1.9847    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8945   -1.5047    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8143   -0.6836    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0631   -0.3425    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0958   -0.6362    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4717   -0.9761    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3505   -1.1000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9566   -0.3087    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.5385    0.6773    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2057    0.6199    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7413   -0.5636    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.6661    0.3853    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1967    1.2611    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3795    0.9585    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7414    0.1918    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3863   -0.0492    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1906   -0.2328    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.9834    0.1399    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5485   -0.9761    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1906   -1.7194    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.8807   -2.3090    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9741   -3.1678    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7412   -2.3407    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3863   -1.9030    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7413   -1.3886    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  4  2  1  1  0  0  0
  4  5  1  6  0  0  0
  5  6  2  0  0  0  0
  5  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
  7 12  1  0  0  0  0
  4 13  1  0  0  0  0
 13 14  2  0  0  0  0
 13 15  1  0  0  0  0
 15 16  1  1  0  0  0
 15 17  1  6  0  0  0
 15 18  1  0  0  0  0
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 18 32  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0158285

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@H]1C[C@H](C[C@H]2[C@](C(C)=O)(C(=O)C3=CC=CC=C3)C(=O)[C@](C)(O)[C@@]2(O1)C(C)(C)O)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C24H30O8/c1-13-11-16(19(27)28)12-17-23(14(2)25,18(26)15-9-7-6-8-10-15)20(29)22(5,31)24(17,32-13)21(3,4)30/h6-10,13,16-17,30-31H,11-12H2,1-5H3,(H,27,28)/t13-,16+,17-,22-,23+,24-/m0/s1

> <INCHI_KEY>
PCHORUFZBQUURI-XNXSLVQRSA-N

> <FORMULA>
C24H30O8

> <MOLECULAR_WEIGHT>
446.496

> <EXACT_MASS>
446.194067926

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_ATOM_COUNT>
62

> <JCHEM_AVERAGE_POLARIZABILITY>
44.99602644011893

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2S,4S,5aS,6S,8R,8aS)-6-acetyl-6-benzoyl-8-hydroxy-8a-(2-hydroxypropan-2-yl)-2,8-dimethyl-7-oxo-octahydro-2H-cyclopenta[b]oxepine-4-carboxylic acid

> <ALOGPS_LOGP>
1.40

> <JCHEM_LOGP>
2.0905140176666657

> <ALOGPS_LOGS>
-2.83

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
12.031117547961989

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.073345498039245

> <JCHEM_PKA_STRONGEST_BASIC>
-3.2423664703150505

> <JCHEM_POLAR_SURFACE_AREA>
138.2

> <JCHEM_REFRACTIVITY>
113.68230000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.63e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2S,4S,5aS,6S,8R,8aS)-6-acetyl-6-benzoyl-8-hydroxy-8a-(2-hydroxypropan-2-yl)-2,8-dimethyl-7-oxo-tetrahydro-2H-cyclopenta[b]oxepine-4-carboxylic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 02-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   02-SEP-22         0                                  
HETATM    1  C   UNK     0       1.969  -6.348   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.021  -4.715   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       3.527  -4.601   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0       1.786  -3.068   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.401  -4.014   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0      -0.292  -5.481   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0      -0.882  -3.068   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -2.284  -3.705   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -3.536  -2.809   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -3.387  -1.276   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -1.985  -0.639   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -0.179  -1.188   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       0.881  -1.822   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0      -0.654  -2.053   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       1.786  -0.576   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       1.005   1.264   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       2.251   1.157   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       3.250  -1.052   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       3.110   0.719   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       2.234   2.354   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       4.442   1.789   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       1.384   0.358   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0       4.454  -0.092   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0       5.956  -0.435   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       7.436   0.261   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       6.624  -1.822   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       5.956  -3.210   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       7.244  -4.310   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0       7.418  -5.913   0.000  0.00  0.00           O+0
HETATM   30  O   UNK     0       8.850  -4.369   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0       4.454  -3.552   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       3.250  -2.592   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5   13   32                                             
CONECT    5    4    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8   12                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11    7                                                       
CONECT   13    4   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13   16   17   18                                             
CONECT   16   15                                                            
CONECT   17   15                                                            
CONECT   18   15   19   23   32                                             
CONECT   19   18   20   21   22                                             
CONECT   20   19                                                            
CONECT   21   19                                                            
CONECT   22   19                                                            
CONECT   23   18   24                                                       
CONECT   24   23   25   26                                                  
CONECT   25   24                                                            
CONECT   26   24   27                                                       
CONECT   27   26   28   31                                                  
CONECT   28   27   29   30                                                  
CONECT   29   28                                                            
CONECT   30   28                                                            
CONECT   31   27   32                                                       
CONECT   32   31    4   18                                                  
MASTER        0    0    0    0    0    0    0    0   32    0   68    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₄H₃₀O₈

Average Mass

446.4960 Da

Monoisotopic Mass

446.19407 Da

IUPAC Name

(2S,4S,5aS,6S,8R,8aS)-6-acetyl-6-benzoyl-8-hydroxy-8a-(2-hydroxypropan-2-yl)-2,8-dimethyl-7-oxo-octahydro-2H-cyclopenta[b]oxepine-4-carboxylic acid

Traditional Name

(2S,4S,5aS,6S,8R,8aS)-6-acetyl-6-benzoyl-8-hydroxy-8a-(2-hydroxypropan-2-yl)-2,8-dimethyl-7-oxo-tetrahydro-2H-cyclopenta[b]oxepine-4-carboxylic acid

CAS Registry Number

Not Available

SMILES

C[C@H]1C[C@H](C[C@H]2[C@](C(C)=O)(C(=O)C3=CC=CC=C3)C(=O)[C@](C)(O)[C@@]2(O1)C(C)(C)O)C(O)=O

InChI Identifier

InChI=1S/C24H30O8/c1-13-11-16(19(27)28)12-17-23(14(2)25,18(26)15-9-7-6-8-10-15)20(29)22(5,31)24(17,32-13)21(3,4)30/h6-10,13,16-17,30-31H,11-12H2,1-5H3,(H,27,28)/t13-,16+,17-,22-,23+,24-/m0/s1

InChI Key

PCHORUFZBQUURI-XNXSLVQRSA-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 geminiflorum	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Sesquiterpenoids

Direct Parent

Sesquiterpenoids

Alternative Parents

Substituents

Sesquiterpenoid
Alkyl-phenylketone
Butyrophenone
Phenylketone
Benzoyl
Aryl alkyl ketone
Aryl ketone
Oxepane
Acyloin
Monocyclic benzene moiety
Benzenoid
Cyclic alcohol
Tertiary alcohol
Cyclic ketone
Ketone
Oxacycle
Carboxylic acid derivative
Carboxylic acid
Organoheterocyclic compound
Dialkyl ether
Ether
Monocarboxylic acid or derivatives
Alcohol
Organic oxide
Hydrocarbon derivative
Organic oxygen compound
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
logP	1.4	ALOGPS
logP	2.09	ChemAxon
logS	-2.8	ALOGPS
pKa (Strongest Acidic)	4.07	ChemAxon
pKa (Strongest Basic)	-3.2	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	138.2 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	113.68 m³·mol⁻¹	ChemAxon
Polarizability	45 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	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

101153552

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (2s,4s,5as,6s,8r,8as)-6-acetyl-6-benzoyl-8-hydroxy-8a-(2-hydroxypropan-2-yl)-2,8-dimethyl-7-oxo-tetrahydro-2h-cyclopenta[b]oxepine-4-carboxylic acid (NP0158285)

MOL for NP0158285 ((2s,4s,5as,6s,8r,8as)-6-acetyl-6-benzoyl-8-hydroxy-8a-(2-hydroxypropan-2-yl)-2,8-dimethyl-7-oxo-tetrahydro-2h-cyclopenta[b]oxepine-4-carboxylic acid)

3D MOL for NP0158285 ((2s,4s,5as,6s,8r,8as)-6-acetyl-6-benzoyl-8-hydroxy-8a-(2-hydroxypropan-2-yl)-2,8-dimethyl-7-oxo-tetrahydro-2h-cyclopenta[b]oxepine-4-carboxylic acid)

3D SDF for NP0158285 ((2s,4s,5as,6s,8r,8as)-6-acetyl-6-benzoyl-8-hydroxy-8a-(2-hydroxypropan-2-yl)-2,8-dimethyl-7-oxo-tetrahydro-2h-cyclopenta[b]oxepine-4-carboxylic acid)

3D-SDF for NP0158285 ((2s,4s,5as,6s,8r,8as)-6-acetyl-6-benzoyl-8-hydroxy-8a-(2-hydroxypropan-2-yl)-2,8-dimethyl-7-oxo-tetrahydro-2h-cyclopenta[b]oxepine-4-carboxylic acid)

PDB for NP0158285 ((2s,4s,5as,6s,8r,8as)-6-acetyl-6-benzoyl-8-hydroxy-8a-(2-hydroxypropan-2-yl)-2,8-dimethyl-7-oxo-tetrahydro-2h-cyclopenta[b]oxepine-4-carboxylic acid)

3D PDB for NP0158285 ((2s,4s,5as,6s,8r,8as)-6-acetyl-6-benzoyl-8-hydroxy-8a-(2-hydroxypropan-2-yl)-2,8-dimethyl-7-oxo-tetrahydro-2h-cyclopenta[b]oxepine-4-carboxylic acid)

SMILES for NP0158285 ((2s,4s,5as,6s,8r,8as)-6-acetyl-6-benzoyl-8-hydroxy-8a-(2-hydroxypropan-2-yl)-2,8-dimethyl-7-oxo-tetrahydro-2h-cyclopenta[b]oxepine-4-carboxylic acid)

INCHI for NP0158285 ((2s,4s,5as,6s,8r,8as)-6-acetyl-6-benzoyl-8-hydroxy-8a-(2-hydroxypropan-2-yl)-2,8-dimethyl-7-oxo-tetrahydro-2h-cyclopenta[b]oxepine-4-carboxylic acid)

Structure for NP0158285 ((2s,4s,5as,6s,8r,8as)-6-acetyl-6-benzoyl-8-hydroxy-8a-(2-hydroxypropan-2-yl)-2,8-dimethyl-7-oxo-tetrahydro-2h-cyclopenta[b]oxepine-4-carboxylic acid)

3D Structure for NP0158285 ((2s,4s,5as,6s,8r,8as)-6-acetyl-6-benzoyl-8-hydroxy-8a-(2-hydroxypropan-2-yl)-2,8-dimethyl-7-oxo-tetrahydro-2h-cyclopenta[b]oxepine-4-carboxylic acid)