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Showing NP-Card for (-)-cis-cleroda-3,13-dien-16-hydroxy-15,18-dioic acid-15,16-olide (NP0331425)

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Record Information
Version1.0
Created at2022-12-25 08:07:48 UTC
Updated at2024-04-19 09:40:41 UTC
NP-MRD IDNP0331425
Secondary Accession NumbersNone
Natural Product Identification
Common Name(-)-cis-cleroda-3,13-dien-16-hydroxy-15,18-dioic acid-15,16-olide
DescriptionPolylauioid J belongs to the class of organic compounds known as colensane and clerodane diterpenoids. These are diterpenoids with a structure based on the clerodane or the colensane skeleton. Clerodanes arise from labdanes by two methyl migrations. It was first documented in 2023 (PMID: 37079954). Based on a literature review a significant number of articles have been published on Polylauioid J (PMID: 37079896) (PMID: 37079770) (PMID: 37079385) (PMID: 37079322).
Structure
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MOLSDFPDBSMILESInChI

MOL for NP0331425 ((-)-cis-cleroda-3,13-dien-16-hydroxy-15,18-dioic acid-15,16-olide)


  Mrv1652312252209072D          

 27 28  0  0  1  0            999 V2000
    0.8986   -2.2820    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.9592   -2.2820    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7717   -2.1387    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3020   -2.7707    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1145   -2.6275    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3966   -1.8522    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6448   -3.2594    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0198   -3.5460    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2074   -3.6892    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9252   -4.4645    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6771   -3.0572    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0000   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.1434    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.1434   -2.0625    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  6  0  0  0
  2  3  1  1  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  6  8  2  0  0  0  0
  5  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 10 12  2  0  0  0  0
  2 13  1  0  0  0  0
 13 14  1  6  0  0  0
 13 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  6  0  0  0
 17 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 20 22  2  0  0  0  0
 19 23  2  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 17 26  1  0  0  0  0
  2 26  1  0  0  0  0
 26 27  1  1  0  0  0
M  END
Download

3D MOL for NP0331425 ((-)-cis-cleroda-3,13-dien-16-hydroxy-15,18-dioic acid-15,16-olide)

Download
3D SDF for NP0331425 ((-)-cis-cleroda-3,13-dien-16-hydroxy-15,18-dioic acid-15,16-olide)

  Mrv1652312252209072D          

 27 28  0  0  1  0            999 V2000
    0.8986   -2.2820    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.9592   -2.2820    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7717   -2.1387    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3020   -2.7707    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1145   -2.6275    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3966   -1.8522    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6448   -3.2594    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0198   -3.5460    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2074   -3.6892    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9252   -4.4645    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6771   -3.0572    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0000   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.1434    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.1434   -2.0625    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  6  0  0  0
  2  3  1  1  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  6  8  2  0  0  0  0
  5  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 10 12  2  0  0  0  0
  2 13  1  0  0  0  0
 13 14  1  6  0  0  0
 13 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  6  0  0  0
 17 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 20 22  2  0  0  0  0
 19 23  2  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 17 26  1  0  0  0  0
  2 26  1  0  0  0  0
 26 27  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0331425

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H][C@]12CCC=C(C(O)=O)[C@]1(C)CC[C@@H](C)[C@]2(C)CC\C(=C/C(O)=O)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C20H28O6/c1-12-7-9-20(3)14(18(25)26)5-4-6-15(20)19(12,2)10-8-13(17(23)24)11-16(21)22/h5,11-12,15H,4,6-10H2,1-3H3,(H,21,22)(H,23,24)(H,25,26)/b13-11+/t12-,15-,19+,20+/m1/s1

> <INCHI_KEY>
BGAUVWFUBPXFPC-QCDLIYEQSA-N

> <FORMULA>
C20H28O6

> <MOLECULAR_WEIGHT>
364.438

> <EXACT_MASS>
364.188588622

$$$$

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3D-SDF for NP0331425 ((-)-cis-cleroda-3,13-dien-16-hydroxy-15,18-dioic acid-15,16-olide)
Download
PDB for NP0331425 ((-)-cis-cleroda-3,13-dien-16-hydroxy-15,18-dioic acid-15,16-olide)
HEADER    PROTEIN                                 25-DEC-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   25-DEC-22         0                                  
HETATM    1  C   UNK     0       1.677  -4.260   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       3.657  -4.260   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       5.174  -3.992   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       6.164  -5.172   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       7.680  -4.905   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       8.207  -3.457   0.000  0.00  0.00           O+0
HETATM    8  O   UNK     0       8.670  -6.084   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       5.637  -6.619   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.120  -6.887   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       3.594  -8.334   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0       3.131  -5.707   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       0.000  -3.080   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       4.001   0.770   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       5.335   1.540   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       4.001   2.310   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0       6.668   2.310   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   27  H   UNK     0       4.001  -3.850   0.000  0.00  0.00           H+0
CONECT    1    2                                                            
CONECT    2    1    3   13   26                                             
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6    9                                                  
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6                                                            
CONECT    9    5   10                                                       
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10                                                            
CONECT   13    2   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18   19   26                                             
CONECT   18   17                                                            
CONECT   19   17   20   23                                                  
CONECT   20   19   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20                                                            
CONECT   23   19   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24   26                                                       
CONECT   26   25   17    2   27                                             
CONECT   27   26                                                            
MASTER        0    0    0    0    0    0    0    0   27    0   56    0
END

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3D PDB for NP0331425 ((-)-cis-cleroda-3,13-dien-16-hydroxy-15,18-dioic acid-15,16-olide)
Download
SMILES for NP0331425 ((-)-cis-cleroda-3,13-dien-16-hydroxy-15,18-dioic acid-15,16-olide)
[H][C@]12CCC=C(C(O)=O)[C@]1(C)CC[C@@H](C)[C@]2(C)CC\C(=C/C(O)=O)C(O)=O
Download
INCHI for NP0331425 ((-)-cis-cleroda-3,13-dien-16-hydroxy-15,18-dioic acid-15,16-olide)
InChI=1S/C20H28O6/c1-12-7-9-20(3)14(18(25)26)5-4-6-15(20)19(12,2)10-8-13(17(23)24)11-16(21)22/h5,11-12,15H,4,6-10H2,1-3H3,(H,21,22)(H,23,24)(H,25,26)/b13-11+/t12-,15-,19+,20+/m1/s1
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View in JSmol
SynonymsNot Available
Chemical FormulaC20H28O6
Average Mass364.4380 Da
Monoisotopic Mass364.18859 Da
IUPAC NameNot Available
Traditional NameNot Available
CAS Registry NumberNot Available
SMILES
[H][C@]12CCC=C(C(O)=O)[C@]1(C)CC[C@@H](C)[C@]2(C)CC\C(=C/C(O)=O)C(O)=O
InChI Identifier
InChI=1S/C20H28O6/c1-12-7-9-20(3)14(18(25)26)5-4-6-15(20)19(12,2)10-8-13(17(23)24)11-16(21)22/h5,11-12,15H,4,6-10H2,1-3H3,(H,21,22)(H,23,24)(H,25,26)/b13-11+/t12-,15-,19+,20+/m1/s1
InChI KeyBGAUVWFUBPXFPC-QCDLIYEQSA-N
Experimental Spectra
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
1D NMR[13C, ] NMR Spectrum (2D, 101 MHz, CD3OD, experimental)wuaizhi@gzucm.edu.cnNot AvailableNot Available2022-12-25View Spectrum
1D NMR[1H, ] NMR Spectrum (2D, 400 MHz, CD3OD, experimental)wuaizhi@gzucm.edu.cnNot AvailableNot Available2022-12-25View Spectrum
1D NMR1H NMR Spectrum (1D, 400.16 MHz, CD3OD, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 100.63 MHz, CD3OD, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of OriginNot Available
Chemical Taxonomy
Description Belongs to the class of organic compounds known as colensane and clerodane diterpenoids. These are diterpenoids with a structure based on the clerodane or the colensane skeleton. Clerodanes arise from labdanes by two methyl migrations.
KingdomOrganic compounds  
Super ClassLipids and lipid-like molecules  
ClassPrenol lipids  
Sub ClassDiterpenoids  
Direct ParentColensane and clerodane diterpenoids  
Alternative Parents
Substituents
  • Clerodane diterpenoid
    • 

  • Tricarboxylic acid or derivatives
    • 

  • Carboxylic acid
    • 

  • Carboxylic acid derivative
    • 

  • Organic oxygen compound
    • 

  • Organic oxide
    • 

  • Hydrocarbon derivative
    • 

  • Organooxygen compound
    • 

  • Carbonyl group
    • 

  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic 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 IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound146001124  
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. Akhlaghpour H: Erratum to "An RNA-based theory of natural universal computation" [J. Theor. Biol. 537 (2022) 110984]. J Theor Biol. 2023 Jun 7;566:111481. doi: 10.1016/j.jtbi.2023.111481. Epub 2023  Apr 18. [PubMed:37079954  ] 
  2. Jian JX, Xie LH, Mumtaz A, Baines T, Major JD, Tong QX, Sun J: Interface-Engineered Ni-Coated CdTe Heterojunction Photocathode for Enhanced Photoelectrochemical Hydrogen Evolution. ACS Appl Mater Interfaces. 2023 May 3;15(17):21057-21065. doi:  10.1021/acsami.3c01476. Epub 2023 Apr 20. [PubMed:37079896  ] 
  3. Yang N, Ryu DH, Lee S, Bai Y, Kim SI, Seo JH, Song CE, Hwang DH: Non-Fullerene Acceptors with Benzodithiophene-Based Fused Planar Ring Cores for Organic Solar Cells. ACS Appl Mater Interfaces. 2023 May 3;15(17):21306-21313. doi:  10.1021/acsami.3c01626. Epub 2023 Apr 20. [PubMed:37079770  ] 
  4. Vadaq N, Zhang Y, Vos WA, Groenendijk AL, Blaauw MJ, van Eekeren LE, Jacobs-Cleophas M, van de Wijer L, Dos Santos JC, Gasem MH, Joosten LA, Netea MG, de Mast Q, Fu J, van der Ven AJ, Matzaraki V: High-throughput proteomic analysis reveals systemic dysregulation in virally suppressed people living with HIV. JCI Insight. 2023 Jun 8;8(11):e166166. doi: 10.1172/jci.insight.166166. [PubMed:37079385  ] 
  5. Radwan AS, Salim MM, Elkhoudary MM, Hadad GM, Shaldam MA, Belal F, Magdy G: Study of the binding interaction of salmon sperm DNA with nintedanib, a tyrosine kinase inhibitor using multi-spectroscopic, thermodynamic, and in silico approaches. J Biomol Struct Dyn. 2024 Feb-Mar;42(3):1170-1180. doi:  10.1080/07391102.2023.2202776. Epub 2023 Apr 20. [PubMed:37079322  ]