NP-MRD: Showing NP-Card for botryosphaerinone (NP0038631)

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Record Information

Version

2.0

Created at

2021-06-20 21:16:13 UTC

Updated at

2021-06-30 00:11:31 UTC

NP-MRD ID

NP0038631

Secondary Accession Numbers

None

Natural Product Identification

Common Name

botryosphaerinone

Provided By

JEOL Database JEOL Logo

Description

2-[(1S,2S)-4-oxo-2-[(2Z)-pent-2-en-1-yl]cyclopentyl]acetic acid belongs to the class of organic compounds known as cyclic ketones. These are organic compounds containing a ketone that is conjugated to a cyclic moiety. botryosphaerinone is found in Botryosphaeria rhodina PSU-M114, Botryosphaeria rhodina PSU-M35, Garcinia mangostana and Lasiodiplodia theobromae. botryosphaerinone was first documented in 2009 (Rukachaisirikul, V., et al.). Based on a literature review very few articles have been published on 2-[(1S,2S)-4-oxo-2-[(2Z)-pent-2-en-1-yl]cyclopentyl]acetic acid.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306202123163D          

 33 33  0  0  0  0            999 V2000
   -1.5020   -2.7997   -3.3357 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4603   -2.2890   -2.2699 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.8178   -2.2895   -0.9115 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5951   -1.2415   -0.1015 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9462    0.2004   -0.3437 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.7009    1.1108   -0.4216 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.2012    0.7812   -1.6227 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.3888    1.6429   -2.7083 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1592    1.4914   -3.9012 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2897    2.7179   -2.1573 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.0271    2.6081   -0.6481 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.1718    3.1605    0.2051 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.2506    4.6647    0.1574 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5000    5.4270   -0.4251 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2934    5.1339    0.8687 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1636   -3.8171   -3.1118 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9977   -2.8170   -4.3117 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6196   -2.1564   -3.4164 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3417   -2.9398   -2.2362 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8147   -1.2968   -2.5610 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5045   -3.2716   -0.5555 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1163   -1.4451    0.8569 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5738    0.5140    0.4992 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5636    0.3215   -1.2379 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1301    0.9955    0.5090 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1972   -0.2703   -1.9113 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2282    1.1147   -1.4416 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0028    3.6962   -2.5502 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3252    2.4845   -2.4206 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1125    3.1771   -0.4227 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0152    2.8764    1.2520 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1345    2.7611   -0.1325 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2388    6.1076    0.7654 H   0  0  0  0  0  0  0  0  0  0  0  0
 11 10  1  0  0  0  0
  8  9  2  0  0  0  0
 10  8  1  0  0  0  0
  5  4  1  0  0  0  0
  8  7  1  0  0  0  0
  4  3  2  0  0  0  0
  7  6  1  0  0  0  0
  3  2  1  0  0  0  0
  6 11  1  0  0  0  0
  2  1  1  0  0  0  0
  6  5  1  0  0  0  0
 12 13  1  0  0  0  0
 13 15  1  0  0  0  0
 11 12  1  0  0  0  0
 13 14  2  0  0  0  0
  6 25  1  1  0  0  0
 11 30  1  6  0  0  0
 10 28  1  0  0  0  0
 10 29  1  0  0  0  0
  7 26  1  0  0  0  0
  7 27  1  0  0  0  0
  5 23  1  0  0  0  0
  5 24  1  0  0  0  0
 12 31  1  0  0  0  0
 12 32  1  0  0  0  0
  4 22  1  0  0  0  0
  3 21  1  0  0  0  0
  2 19  1  0  0  0  0
  2 20  1  0  0  0  0
  1 16  1  0  0  0  0
  1 17  1  0  0  0  0
  1 18  1  0  0  0  0
 15 33  1  0  0  0  0
M  END

     RDKit          3D

 33 33  0  0  0  0  0  0  0  0999 V2000
   -1.5020   -2.7997   -3.3357 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4603   -2.2890   -2.2699 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8178   -2.2895   -0.9115 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5951   -1.2415   -0.1015 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9462    0.2004   -0.3437 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7009    1.1108   -0.4216 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.2012    0.7812   -1.6227 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3888    1.6429   -2.7083 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1592    1.4914   -3.9012 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2897    2.7179   -2.1573 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0271    2.6081   -0.6481 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.1718    3.1605    0.2051 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2506    4.6647    0.1574 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5000    5.4270   -0.4251 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2934    5.1339    0.8687 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1636   -3.8171   -3.1118 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9977   -2.8170   -4.3117 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6196   -2.1564   -3.4164 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3417   -2.9398   -2.2362 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8147   -1.2968   -2.5610 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5045   -3.2716   -0.5555 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1163   -1.4451    0.8569 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5738    0.5140    0.4992 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5636    0.3215   -1.2379 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1301    0.9955    0.5090 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1972   -0.2703   -1.9113 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2282    1.1147   -1.4416 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0028    3.6962   -2.5502 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3252    2.4845   -2.4206 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1125    3.1771   -0.4227 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0152    2.8764    1.2520 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1345    2.7611   -0.1325 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2388    6.1076    0.7654 H   0  0  0  0  0  0  0  0  0  0  0  0
 11 10  1  0
  8  9  2  0
 10  8  1  0
  5  4  1  0
  8  7  1  0
  4  3  2  0
  7  6  1  0
  3  2  1  0
  6 11  1  0
  2  1  1  0
  6  5  1  0
 12 13  1  0
 13 15  1  0
 11 12  1  0
 13 14  2  0
  6 25  1  1
 11 30  1  6
 10 28  1  0
 10 29  1  0
  7 26  1  0
  7 27  1  0
  5 23  1  0
  5 24  1  0
 12 31  1  0
 12 32  1  0
  4 22  1  0
  3 21  1  0
  2 19  1  0
  2 20  1  0
  1 16  1  0
  1 17  1  0
  1 18  1  0
 15 33  1  0
M  END


  Mrv1652306202123163D          

 33 33  0  0  0  0            999 V2000
   -1.5020   -2.7997   -3.3357 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4603   -2.2890   -2.2699 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.8178   -2.2895   -0.9115 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5951   -1.2415   -0.1015 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9462    0.2004   -0.3437 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.7009    1.1108   -0.4216 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.2012    0.7812   -1.6227 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.3888    1.6429   -2.7083 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1592    1.4914   -3.9012 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2897    2.7179   -2.1573 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.0271    2.6081   -0.6481 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.1718    3.1605    0.2051 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.2506    4.6647    0.1574 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5000    5.4270   -0.4251 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2934    5.1339    0.8687 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1636   -3.8171   -3.1118 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9977   -2.8170   -4.3117 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6196   -2.1564   -3.4164 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3417   -2.9398   -2.2362 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8147   -1.2968   -2.5610 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5045   -3.2716   -0.5555 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1163   -1.4451    0.8569 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5738    0.5140    0.4992 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5636    0.3215   -1.2379 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1301    0.9955    0.5090 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1972   -0.2703   -1.9113 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2282    1.1147   -1.4416 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0028    3.6962   -2.5502 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3252    2.4845   -2.4206 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1125    3.1771   -0.4227 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0152    2.8764    1.2520 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1345    2.7611   -0.1325 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2388    6.1076    0.7654 H   0  0  0  0  0  0  0  0  0  0  0  0
 11 10  1  0  0  0  0
  8  9  2  0  0  0  0
 10  8  1  0  0  0  0
  5  4  1  0  0  0  0
  8  7  1  0  0  0  0
  4  3  2  0  0  0  0
  7  6  1  0  0  0  0
  3  2  1  0  0  0  0
  6 11  1  0  0  0  0
  2  1  1  0  0  0  0
  6  5  1  0  0  0  0
 12 13  1  0  0  0  0
 13 15  1  0  0  0  0
 11 12  1  0  0  0  0
 13 14  2  0  0  0  0
  6 25  1  1  0  0  0
 11 30  1  6  0  0  0
 10 28  1  0  0  0  0
 10 29  1  0  0  0  0
  7 26  1  0  0  0  0
  7 27  1  0  0  0  0
  5 23  1  0  0  0  0
  5 24  1  0  0  0  0
 12 31  1  0  0  0  0
 12 32  1  0  0  0  0
  4 22  1  0  0  0  0
  3 21  1  0  0  0  0
  2 19  1  0  0  0  0
  2 20  1  0  0  0  0
  1 16  1  0  0  0  0
  1 17  1  0  0  0  0
  1 18  1  0  0  0  0
 15 33  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0038631

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC(=O)C([H])([H])[C@]1([H])C([H])([H])C(=O)C([H])([H])[C@]1([H])C([H])([H])C(\[H])=C(\[H])C([H])([H])C([H])([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C12H18O3/c1-2-3-4-5-9-6-11(13)7-10(9)8-12(14)15/h3-4,9-10H,2,5-8H2,1H3,(H,14,15)/b4-3-/t9-,10-/m0/s1

> <INCHI_KEY>
AUAYBDNKDWXWEX-CMIOBCHKSA-N

> <FORMULA>
C12H18O3

> <MOLECULAR_WEIGHT>
210.273

> <EXACT_MASS>
210.12559444

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
33

> <JCHEM_AVERAGE_POLARIZABILITY>
23.10117540427138

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-[(1S,2S)-4-oxo-2-[(2Z)-pent-2-en-1-yl]cyclopentyl]acetic acid

> <ALOGPS_LOGP>
2.39

> <JCHEM_LOGP>
2.158343695666667

> <ALOGPS_LOGS>
-2.37

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.714082743036221

> <JCHEM_PKA_STRONGEST_BASIC>
-7.35800293291963

> <JCHEM_POLAR_SURFACE_AREA>
54.370000000000005

> <JCHEM_REFRACTIVITY>
58.53060000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
8.96e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
[(1S,2S)-4-oxo-2-[(2Z)-pent-2-en-1-yl]cyclopentyl]acetic acid

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 33 33  0  0  0  0  0  0  0  0999 V2000
   -1.5020   -2.7997   -3.3357 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4603   -2.2890   -2.2699 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8178   -2.2895   -0.9115 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5951   -1.2415   -0.1015 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9462    0.2004   -0.3437 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7009    1.1108   -0.4216 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.2012    0.7812   -1.6227 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3888    1.6429   -2.7083 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1592    1.4914   -3.9012 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2897    2.7179   -2.1573 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0271    2.6081   -0.6481 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.1718    3.1605    0.2051 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2506    4.6647    0.1574 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5000    5.4270   -0.4251 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2934    5.1339    0.8687 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1636   -3.8171   -3.1118 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9977   -2.8170   -4.3117 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6196   -2.1564   -3.4164 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3417   -2.9398   -2.2362 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8147   -1.2968   -2.5610 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5045   -3.2716   -0.5555 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1163   -1.4451    0.8569 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5738    0.5140    0.4992 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5636    0.3215   -1.2379 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1301    0.9955    0.5090 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1972   -0.2703   -1.9113 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2282    1.1147   -1.4416 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0028    3.6962   -2.5502 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3252    2.4845   -2.4206 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1125    3.1771   -0.4227 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0152    2.8764    1.2520 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1345    2.7611   -0.1325 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2388    6.1076    0.7654 H   0  0  0  0  0  0  0  0  0  0  0  0
 11 10  1  0
  8  9  2  0
 10  8  1  0
  5  4  1  0
  8  7  1  0
  4  3  2  0
  7  6  1  0
  3  2  1  0
  6 11  1  0
  2  1  1  0
  6  5  1  0
 12 13  1  0
 13 15  1  0
 11 12  1  0
 13 14  2  0
  6 25  1  1
 11 30  1  6
 10 28  1  0
 10 29  1  0
  7 26  1  0
  7 27  1  0
  5 23  1  0
  5 24  1  0
 12 31  1  0
 12 32  1  0
  4 22  1  0
  3 21  1  0
  2 19  1  0
  2 20  1  0
  1 16  1  0
  1 17  1  0
  1 18  1  0
 15 33  1  0
M  END

HEADER    PROTEIN                                 20-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   20-JUN-21         0                                  
HETATM    1  C   UNK     0      -1.502  -2.800  -3.336  0.00  0.00           C+0
HETATM    2  C   UNK     0      -2.460  -2.289  -2.270  0.00  0.00           C+0
HETATM    3  C   UNK     0      -1.818  -2.289  -0.912  0.00  0.00           C+0
HETATM    4  C   UNK     0      -1.595  -1.242  -0.102  0.00  0.00           C+0
HETATM    5  C   UNK     0      -1.946   0.200  -0.344  0.00  0.00           C+0
HETATM    6  C   UNK     0      -0.701   1.111  -0.422  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.201   0.781  -1.623  0.00  0.00           C+0
HETATM    8  C   UNK     0      -0.389   1.643  -2.708  0.00  0.00           C+0
HETATM    9  O   UNK     0      -0.159   1.491  -3.901  0.00  0.00           O+0
HETATM   10  C   UNK     0      -1.290   2.718  -2.157  0.00  0.00           C+0
HETATM   11  C   UNK     0      -1.027   2.608  -0.648  0.00  0.00           C+0
HETATM   12  C   UNK     0      -2.172   3.160   0.205  0.00  0.00           C+0
HETATM   13  C   UNK     0      -2.251   4.665   0.157  0.00  0.00           C+0
HETATM   14  O   UNK     0      -1.500   5.427  -0.425  0.00  0.00           O+0
HETATM   15  O   UNK     0      -3.293   5.134   0.869  0.00  0.00           O+0
HETATM   16  H   UNK     0      -1.164  -3.817  -3.112  0.00  0.00           H+0
HETATM   17  H   UNK     0      -1.998  -2.817  -4.312  0.00  0.00           H+0
HETATM   18  H   UNK     0      -0.620  -2.156  -3.416  0.00  0.00           H+0
HETATM   19  H   UNK     0      -3.342  -2.940  -2.236  0.00  0.00           H+0
HETATM   20  H   UNK     0      -2.815  -1.297  -2.561  0.00  0.00           H+0
HETATM   21  H   UNK     0      -1.504  -3.272  -0.556  0.00  0.00           H+0
HETATM   22  H   UNK     0      -1.116  -1.445   0.857  0.00  0.00           H+0
HETATM   23  H   UNK     0      -2.574   0.514   0.499  0.00  0.00           H+0
HETATM   24  H   UNK     0      -2.564   0.322  -1.238  0.00  0.00           H+0
HETATM   25  H   UNK     0      -0.130   0.996   0.509  0.00  0.00           H+0
HETATM   26  H   UNK     0       0.197  -0.270  -1.911  0.00  0.00           H+0
HETATM   27  H   UNK     0       1.228   1.115  -1.442  0.00  0.00           H+0
HETATM   28  H   UNK     0      -1.003   3.696  -2.550  0.00  0.00           H+0
HETATM   29  H   UNK     0      -2.325   2.485  -2.421  0.00  0.00           H+0
HETATM   30  H   UNK     0      -0.113   3.177  -0.423  0.00  0.00           H+0
HETATM   31  H   UNK     0      -2.015   2.876   1.252  0.00  0.00           H+0
HETATM   32  H   UNK     0      -3.135   2.761  -0.133  0.00  0.00           H+0
HETATM   33  H   UNK     0      -3.239   6.108   0.765  0.00  0.00           H+0
CONECT    1    2   16   17   18                                             
CONECT    2    3    1   19   20                                             
CONECT    3    4    2   21                                                  
CONECT    4    5    3   22                                                  
CONECT    5    4    6   23   24                                             
CONECT    6    7   11    5   25                                             
CONECT    7    8    6   26   27                                             
CONECT    8    9   10    7                                                  
CONECT    9    8                                                            
CONECT   10   11    8   28   29                                             
CONECT   11   10    6   12   30                                             
CONECT   12   13   11   31   32                                             
CONECT   13   12   15   14                                                  
CONECT   14   13                                                            
CONECT   15   13   33                                                       
CONECT   16    1                                                            
CONECT   17    1                                                            
CONECT   18    1                                                            
CONECT   19    2                                                            
CONECT   20    2                                                            
CONECT   21    3                                                            
CONECT   22    4                                                            
CONECT   23    5                                                            
CONECT   24    5                                                            
CONECT   25    6                                                            
CONECT   26    7                                                            
CONECT   27    7                                                            
CONECT   28   10                                                            
CONECT   29   10                                                            
CONECT   30   11                                                            
CONECT   31   12                                                            
CONECT   32   12                                                            
CONECT   33   15                                                            
MASTER        0    0    0    0    0    0    0    0   33    0   66    0
END

RDKit          3D

33 33  0  0  0  0  0  0  0  0999 V2000
   -1.5020   -2.7997   -3.3357 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4603   -2.2890   -2.2699 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8178   -2.2895   -0.9115 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5951   -1.2415   -0.1015 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9462    0.2004   -0.3437 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7009    1.1108   -0.4216 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.2012    0.7812   -1.6227 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3888    1.6429   -2.7083 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1592    1.4914   -3.9012 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2897    2.7179   -2.1573 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0271    2.6081   -0.6481 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.1718    3.1605    0.2051 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2506    4.6647    0.1574 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5000    5.4270   -0.4251 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2934    5.1339    0.8687 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1636   -3.8171   -3.1118 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9977   -2.8170   -4.3117 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6196   -2.1564   -3.4164 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3417   -2.9398   -2.2362 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8147   -1.2968   -2.5610 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5045   -3.2716   -0.5555 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1163   -1.4451    0.8569 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5738    0.5140    0.4992 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5636    0.3215   -1.2379 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1301    0.9955    0.5090 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1972   -0.2703   -1.9113 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2282    1.1147   -1.4416 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0028    3.6962   -2.5502 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3252    2.4845   -2.4206 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1125    3.1771   -0.4227 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0152    2.8764    1.2520 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1345    2.7611   -0.1325 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2388    6.1076    0.7654 H   0  0  0  0  0  0  0  0  0  0  0  0
 11 10  1  0
  8  9  2  0
 10  8  1  0
  5  4  1  0
  8  7  1  0
  4  3  2  0
  7  6  1  0
  3  2  1  0
  6 11  1  0
  2  1  1  0
  6  5  1  0
 12 13  1  0
 13 15  1  0
 11 12  1  0
 13 14  2  0
  6 25  1  1
 11 30  1  6
 10 28  1  0
 10 29  1  0
  7 26  1  0
  7 27  1  0
  5 23  1  0
  5 24  1  0
 12 31  1  0
 12 32  1  0
  4 22  1  0
  3 21  1  0
  2 19  1  0
  2 20  1  0
  1 16  1  0
  1 17  1  0
  1 18  1  0
 15 33  1  0
M  END

View in JSmol

Synonyms

Value	Source
2-[(1S,2S)-4-oxo-2-[(2Z)-Pent-2-en-1-yl]cyclopentyl]acetate	Generator

Chemical Formula

C₁₂H₁₈O₃

Average Mass

210.2730 Da

Monoisotopic Mass

210.12559 Da

IUPAC Name

2-[(1S,2S)-4-oxo-2-[(2Z)-pent-2-en-1-yl]cyclopentyl]acetic acid

Traditional Name

[(1S,2S)-4-oxo-2-[(2Z)-pent-2-en-1-yl]cyclopentyl]acetic acid

CAS Registry Number

Not Available

SMILES

[H]OC(=O)C([H])([H])[C@]1([H])C([H])([H])C(=O)C([H])([H])[C@]1([H])C([H])([H])C(\[H])=C(\[H])C([H])([H])C([H])([H])[H]

InChI Identifier

InChI=1S/C12H18O3/c1-2-3-4-5-9-6-11(13)7-10(9)8-12(14)15/h3-4,9-10H,2,5-8H2,1H3,(H,14,15)/b4-3-/t9-,10-/m0/s1

InChI Key

AUAYBDNKDWXWEX-CMIOBCHKSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Botryosphaeria rhodina PSU-M114	JEOL database	Rukachaisirikul, V., et al, Tetrahedron 65, 10590 (2009)
Botryosphaeria rhodina PSU-M35	JEOL database	Rukachaisirikul, V., et al, Tetrahedron 65, 10590 (2009)
Garcinia mangostana	LOTUS Database	35616633
Lasiodiplodia theobromae	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as cyclic ketones. These are organic compounds containing a ketone that is conjugated to a cyclic moiety.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbonyl compounds

Direct Parent

Cyclic ketones

Alternative Parents

Substituents

Cyclic ketone
Monocarboxylic acid or derivatives
Carboxylic acid
Carboxylic acid derivative
Organic oxide
Hydrocarbon derivative
Aliphatic homomonocyclic compound

Molecular Framework

Aliphatic homomonocyclic 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	2.39	ALOGPS
logP	2.16	ChemAxon
logS	-2.4	ALOGPS
pKa (Strongest Acidic)	4.71	ChemAxon
pKa (Strongest Basic)	-7.4	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	54.37 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	58.53 m³·mol⁻¹	ChemAxon
Polarizability	23.1 Å³	ChemAxon
Number of Rings	1	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

75143091

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

102161310

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Rukachaisirikul, V., et al. (2009). Rukachaisirikul, V., et al, Tetrahedron 65, 10590 (2009). Tetrahedron.

Showing NP-Card for botryosphaerinone (NP0038631)

MOL for NP0038631 (botryosphaerinone)

3D MOL for NP0038631 (botryosphaerinone)

3D SDF for NP0038631 (botryosphaerinone)

3D-SDF for NP0038631 (botryosphaerinone)

PDB for NP0038631 (botryosphaerinone)

3D PDB for NP0038631 (botryosphaerinone)

SMILES for NP0038631 (botryosphaerinone)

INCHI for NP0038631 (botryosphaerinone)

Structure for NP0038631 (botryosphaerinone)

3D Structure for NP0038631 (botryosphaerinone)