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Showing NP-Card for (4s,5s)-4,5-dihydroxy-3-[(1e)-prop-1-en-1-yl]cyclopent-2-en-1-one (NP0324484)

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Record Information
Version2.0
Created at2022-09-12 04:35:27 UTC
Updated at2022-09-12 04:35:27 UTC
NP-MRD IDNP0324484
Secondary Accession NumbersNone
Natural Product Identification
Common Name(4s,5s)-4,5-dihydroxy-3-[(1e)-prop-1-en-1-yl]cyclopent-2-en-1-one
DescriptionIsoterrein belongs to the class of organic compounds known as 1,2-diols. These are polyols containing an alcohol group at two adjacent positions. (4s,5s)-4,5-dihydroxy-3-[(1e)-prop-1-en-1-yl]cyclopent-2-en-1-one was first documented in 2018 (PMID: 29657234). Based on a literature review very few articles have been published on Isoterrein.
Structure
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MOL3D MOLSDFPDBSMILESInChI

MOL for NP0324484 ((4s,5s)-4,5-dihydroxy-3-[(1e)-prop-1-en-1-yl]cyclopent-2-en-1-one)


  Mrv1652309122206352D          

 11 11  0  0  1  0            999 V2000
   -0.1467    3.1768    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1467    2.3518    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5678    1.9393    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5678    1.1143    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2352    0.6294    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9803   -0.1553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4652   -0.8227    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1553   -0.1553    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.3297   -0.8227    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0997    0.6294    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.8843    0.8843    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  6  8  1  0  0  0  0
  8  9  1  1  0  0  0
  8 10  1  0  0  0  0
  4 10  1  0  0  0  0
 10 11  1  1  0  0  0
M  END
Download

3D MOL for NP0324484 ((4s,5s)-4,5-dihydroxy-3-[(1e)-prop-1-en-1-yl]cyclopent-2-en-1-one)

     RDKit          3D

 21 21  0  0  0  0  0  0  0  0999 V2000
    3.5125    0.1009   -0.9258 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0365   -0.0760   -0.7091 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3807    0.5625    0.2427 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0748    0.3700    0.4349 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8479    0.9369    1.3351 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2300    0.4756    1.1874 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2605    1.0606    1.5488 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0623   -0.8585    0.4997 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.2015   -1.2012   -0.2086 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9009   -0.5167   -0.4005 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.4006    0.2314   -1.4637 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8673    0.7516   -0.0996 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7268    0.5491   -1.8966 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9648   -0.9017   -0.7854 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4692   -0.7525   -1.3522 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9556    1.2291    0.8714 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4833    1.6444    2.0710 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7952   -1.5758    1.2925 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7968   -1.7941    0.3167 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3567   -1.4193   -0.7454 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5029    1.1836   -1.2133 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
  4  5  2  0
  5  6  1  0
  6  7  2  0
  6  8  1  0
  8  9  1  0
  8 10  1  0
 10 11  1  0
 10  4  1  0
  1 12  1  0
  1 13  1  0
  1 14  1  0
  2 15  1  0
  3 16  1  0
  5 17  1  0
  8 18  1  1
  9 19  1  0
 10 20  1  6
 11 21  1  0
M  END
Download

3D SDF for NP0324484 ((4s,5s)-4,5-dihydroxy-3-[(1e)-prop-1-en-1-yl]cyclopent-2-en-1-one)


  Mrv1652309122206352D          

 11 11  0  0  1  0            999 V2000
   -0.1467    3.1768    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1467    2.3518    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5678    1.9393    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5678    1.1143    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2352    0.6294    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9803   -0.1553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4652   -0.8227    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1553   -0.1553    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.3297   -0.8227    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0997    0.6294    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.8843    0.8843    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  6  8  1  0  0  0  0
  8  9  1  1  0  0  0
  8 10  1  0  0  0  0
  4 10  1  0  0  0  0
 10 11  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0324484

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C\C=C\C1=CC(=O)[C@@H](O)[C@H]1O

> <INCHI_IDENTIFIER>
InChI=1S/C8H10O3/c1-2-3-5-4-6(9)8(11)7(5)10/h2-4,7-8,10-11H,1H3/b3-2+/t7-,8+/m0/s1

> <INCHI_KEY>
MHOOPNKRBMHHEC-RIAPOHOLSA-N

> <FORMULA>
C8H10O3

> <MOLECULAR_WEIGHT>
154.165

> <EXACT_MASS>
154.062994182

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
21

> <JCHEM_AVERAGE_POLARIZABILITY>
15.761092452269859

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(4S,5S)-4,5-dihydroxy-3-[(1E)-prop-1-en-1-yl]cyclopent-2-en-1-one

> <JCHEM_LOGP>
0.021963966666666473

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.211256114862422

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.311488205100407

> <JCHEM_PKA_STRONGEST_BASIC>
-3.5228885354846042

> <JCHEM_POLAR_SURFACE_AREA>
57.53

> <JCHEM_REFRACTIVITY>
42.04

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(4S,5S)-4,5-dihydroxy-3-[(1E)-prop-1-en-1-yl]cyclopent-2-en-1-one

> <JCHEM_VEBER_RULE>
0

$$$$
Download

3D-SDF for NP0324484 ((4s,5s)-4,5-dihydroxy-3-[(1e)-prop-1-en-1-yl]cyclopent-2-en-1-one)

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PDB for NP0324484 ((4s,5s)-4,5-dihydroxy-3-[(1e)-prop-1-en-1-yl]cyclopent-2-en-1-one)
HEADER    PROTEIN                                 12-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   12-SEP-22         0                                  
HETATM    1  C   UNK     0      -0.274   5.930   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -0.274   4.390   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.060   3.620   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.060   2.080   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.306   1.175   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.830  -0.290   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       2.735  -1.536   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       0.290  -0.290   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0      -0.615  -1.536   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0      -0.186   1.175   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      -1.651   1.651   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5   10                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8    4   11                                                  
CONECT   11   10                                                            
MASTER        0    0    0    0    0    0    0    0   11    0   22    0
END

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3D PDB for NP0324484 ((4s,5s)-4,5-dihydroxy-3-[(1e)-prop-1-en-1-yl]cyclopent-2-en-1-one)
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SMILES for NP0324484 ((4s,5s)-4,5-dihydroxy-3-[(1e)-prop-1-en-1-yl]cyclopent-2-en-1-one)
C\C=C\C1=CC(=O)[C@@H](O)[C@H]1O
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INCHI for NP0324484 ((4s,5s)-4,5-dihydroxy-3-[(1e)-prop-1-en-1-yl]cyclopent-2-en-1-one)
InChI=1S/C8H10O3/c1-2-3-5-4-6(9)8(11)7(5)10/h2-4,7-8,10-11H,1H3/b3-2+/t7-,8+/m0/s1
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View in JSmol
SynonymsNot Available
Chemical FormulaC8H10O3
Average Mass154.1650 Da
Monoisotopic Mass154.06299 Da
IUPAC NameNot Available
Traditional NameNot Available
CAS Registry NumberNot Available
SMILES
C\C=C\C1=CC(=O)[C@@H](O)[C@H]1O
InChI Identifier
InChI=1S/C8H10O3/c1-2-3-5-4-6(9)8(11)7(5)10/h2-4,7-8,10-11H,1H3/b3-2+/t7-,8+/m0/s1
InChI KeyMHOOPNKRBMHHEC-RIAPOHOLSA-N
Experimental Spectra
Not Available
Predicted Spectra
Spectrum TypeDescriptionDepositor IDDepositor OrganizationDepositorDeposition DateView
1D NMR13C NMR Spectrum (1D, 25 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 252 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 50 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 75 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 101 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 126 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 151 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 176 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 201 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 226 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Chemical Shift Submissions
Not Available
Species
Species of OriginNot Available
Chemical Taxonomy
Description Belongs to the class of organic compounds known as 1,2-diols. These are polyols containing an alcohol group at two adjacent positions.
KingdomOrganic compounds  
Super ClassOrganic oxygen compounds  
ClassOrganooxygen compounds  
Sub ClassAlcohols and polyols  
Direct Parent1,2-diols  
Alternative Parents
Substituents
  • Cyclic ketone
    • 

  • Secondary alcohol
    • 

  • Ketone
    • 

  • 1,2-diol
    • 

  • Organic oxide
    • 

  • Hydrocarbon derivative
    • 

  • Carbonyl group
    • 

  • Aliphatic homomonocyclic compound
Molecular FrameworkAliphatic homomonocyclic compounds
External DescriptorsNot Available
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID9085035  
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound10909778  
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. Zhang X, Wu Z, Lai Y, Li D, Wang J, Luo Z, Xue Y, Zhu H, Chen C, Zhang Y: (+/-)-Terreinlactone A, a Pair of 3-Substituted delta-Lactone Enantiomers Derived from Terrein from the Fungus Aspergillus terreus. Chem Pharm Bull (Tokyo). 2018 Jul 1;66(7):764-767. doi: 10.1248/cpb.c18-00200. Epub 2018 Apr 13. [PubMed:29657234  ] 
  2. LOTUS database [Link]