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Showing NP-Card for ramulosin (NP0236367)

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Record Information
Version2.0
Created at2022-09-06 19:15:12 UTC
Updated at2022-09-06 19:15:12 UTC
NP-MRD IDNP0236367
Secondary Accession NumbersNone
Natural Product Identification
Common Nameramulosin
DescriptionRAMULOSIN belongs to the class of organic compounds known as benzopyrans. These are organic compounds containing a benzene ring fused to a pyran ring. Pyran a six-membered heterocyclic, non-aromatic ring, made up of five carbon atoms and one oxygen atom and containing two double bonds. ramulosin is found in Truncatella laurocerasi. ramulosin was first documented in 2007 (PMID: 17541203). Based on a literature review a significant number of articles have been published on RAMULOSIN (PMID: 27556953) (PMID: 28384525) (PMID: 25920279) (PMID: 33562648) (PMID: 27775130) (PMID: 26077652).
Structure
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MOL3D MOLSDFPDBSMILESInChI

MOL for NP0236367 (ramulosin)


  Mrv1652309062221152D          

 13 14  0  0  1  0            999 V2000
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  2  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  2  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
    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
    2.8579   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  6  0  0  0
  2  3  1  0  0  0  0
  4  3  1  6  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  8 10  2  0  0  0  0
  4 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 11 13  1  0  0  0  0
  2 13  1  0  0  0  0
M  END
Download

3D MOL for NP0236367 (ramulosin)

     RDKit          3D

 27 28  0  0  0  0  0  0  0  0999 V2000
    3.1746   -0.1992   -0.3645 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2106    0.1254    0.7711 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.0910   -0.8540    0.7738 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2730   -0.2258    0.9435 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.2880   -1.3209    0.7558 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9390   -1.1580   -0.5945 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6424    0.2097   -0.5769 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5262    1.1889   -0.6166 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5947    2.3485   -1.3924 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4573    0.9513    0.0953 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6623    1.9147    0.0652 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5117    3.0301   -0.4502 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8453    1.4620    0.6469 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1541    0.3324   -0.1873 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7380    0.1287   -1.3281 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3463   -1.2986   -0.3344 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7663    0.0190    1.7394 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0637   -1.4299   -0.1741 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2082   -1.6046    1.5865 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3216    0.1477    2.0092 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8217   -2.3337    0.7598 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0478   -1.3242    1.5684 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6445   -1.9609   -0.8351 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1359   -1.0748   -1.3425 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1812    0.3615    0.3678 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2652    0.2894   -1.4790 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6334    2.2754   -2.4070 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  8 10  2  0
 10 11  1  0
 11 12  2  0
 11 13  1  0
 13  2  1  0
 10  4  1  0
  1 14  1  0
  1 15  1  0
  1 16  1  0
  2 17  1  1
  3 18  1  0
  3 19  1  0
  4 20  1  1
  5 21  1  0
  5 22  1  0
  6 23  1  0
  6 24  1  0
  7 25  1  0
  7 26  1  0
  9 27  1  0
M  END
Download

3D SDF for NP0236367 (ramulosin)


  Mrv1652309062221152D          

 13 14  0  0  1  0            999 V2000
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  2  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  2  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
    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
    2.8579   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  6  0  0  0
  2  3  1  0  0  0  0
  4  3  1  6  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  8 10  2  0  0  0  0
  4 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 11 13  1  0  0  0  0
  2 13  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0236367

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@@H]1C[C@@H]2CCCC(O)=C2C(=O)O1

> <INCHI_IDENTIFIER>
InChI=1S/C10H14O3/c1-6-5-7-3-2-4-8(11)9(7)10(12)13-6/h6-7,11H,2-5H2,1H3/t6-,7+/m1/s1

> <INCHI_KEY>
XQHOYOKXFNTNQZ-RQJHMYQMSA-N

> <FORMULA>
C10H14O3

> <MOLECULAR_WEIGHT>
182.219

> <EXACT_MASS>
182.094294311

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
27

> <JCHEM_AVERAGE_POLARIZABILITY>
19.170892314526515

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(3R,4aS)-8-hydroxy-3-methyl-3,4,4a,5,6,7-hexahydro-1H-2-benzopyran-1-one

> <JCHEM_LOGP>
1.5230784723333333

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.819473126478922

> <JCHEM_PKA_STRONGEST_BASIC>
-5.064762454478118

> <JCHEM_POLAR_SURFACE_AREA>
46.53

> <JCHEM_REFRACTIVITY>
48.773

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(3R,4aS)-8-hydroxy-3-methyl-3,4,4a,5,6,7-hexahydro-2-benzopyran-1-one

> <JCHEM_VEBER_RULE>
0

$$$$
Download

3D-SDF for NP0236367 (ramulosin)

Download
PDB for NP0236367 (ramulosin)
HEADER    PROTEIN                                 06-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-SEP-22         0                                  
HETATM    1  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       5.335  -4.620   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       2.667  -4.620   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0       1.334  -2.310   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   13                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5   10                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8    4   11                                                  
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11    2                                                       
MASTER        0    0    0    0    0    0    0    0   13    0   28    0
END

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3D PDB for NP0236367 (ramulosin)
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SMILES for NP0236367 (ramulosin)
C[C@@H]1C[C@@H]2CCCC(O)=C2C(=O)O1
Download
INCHI for NP0236367 (ramulosin)
InChI=1S/C10H14O3/c1-6-5-7-3-2-4-8(11)9(7)10(12)13-6/h6-7,11H,2-5H2,1H3/t6-,7+/m1/s1
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View in JSmol
SynonymsNot Available
Chemical FormulaC10H14O3
Average Mass182.2190 Da
Monoisotopic Mass182.09429 Da
IUPAC NameNot Available
Traditional NameNot Available
CAS Registry NumberNot Available
SMILES
C[C@@H]1C[C@@H]2CCCC(O)=C2C(=O)O1
InChI Identifier
InChI=1S/C10H14O3/c1-6-5-7-3-2-4-8(11)9(7)10(12)13-6/h6-7,11H,2-5H2,1H3/t6-,7+/m1/s1
InChI KeyXQHOYOKXFNTNQZ-RQJHMYQMSA-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 Origin
Species NameSourceReference
Truncatella laurocerasiLOTUS Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as benzopyrans. These are organic compounds containing a benzene ring fused to a pyran ring. Pyran a six-membered heterocyclic, non-aromatic ring, made up of five carbon atoms and one oxygen atom and containing two double bonds.
KingdomOrganic compounds  
Super ClassOrganoheterocyclic compounds  
ClassBenzopyrans  
Sub ClassNot Available
Direct ParentBenzopyrans  
Alternative Parents
Substituents
  • Benzopyran
    • 

  • Delta valerolactone
    • 

  • Delta_valerolactone
    • 

  • Oxane
    • 

  • Vinylogous acid
    • 

  • Alpha,beta-unsaturated carboxylic ester
    • 

  • Enoate ester
    • 

  • Carboxylic acid ester
    • 

  • Lactone
    • 

  • Monocarboxylic acid or derivatives
    • 

  • Enol
    • 

  • Carboxylic acid derivative
    • 

  • Oxacycle
    • 

  • Organic oxygen compound
    • 

  • Hydrocarbon derivative
    • 

  • Organic oxide
    • 

  • Carbonyl group
    • 

  • Organooxygen compound
    • 

  • Aliphatic heteropolycyclic compound
Molecular FrameworkAliphatic heteropolycyclic 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 ID24536430  
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound54686269  
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. El-Beih AA, Kato H, Ohta T, Tsukamoto S: (3R,4aR,5S,6R)-6-Hydroxy-5-methylramulosin: a new ramulosin derivative from a marine-derived sterile mycelium. Chem Pharm Bull (Tokyo). 2007 Jun;55(6):953-4. doi: 10.1248/cpb.55.953. [PubMed:17541203  ] 
  2. Zhou YH, Zhang M, Zhu RX, Zhang JZ, Xie F, Li XB, Chang WQ, Wang XN, Zhao ZT, Lou HX: Heptaketides from an Endolichenic Fungus Biatriospora sp. and Their Antifungal Activity. J Nat Prod. 2016 Sep 23;79(9):2149-57. doi: 10.1021/acs.jnatprod.5b00998. Epub 2016 Aug 24. [PubMed:27556953  ] 
  3. Intaraudom C, Bunbamrung N, Dramae A, Boonyuen N, Kongsaeree P, Srichomthong K, Supothina S, Pittayakhajonwut P: Terphenyl derivatives and drimane - Phathalide/isoindolinones from Hypoxylon fendleri BCC32408. Phytochemistry. 2017 Jul;139:8-17. doi: 10.1016/j.phytochem.2017.03.008. Epub 2017 Apr 3. [PubMed:28384525  ] 
  4. Chen S, Zhang Z, Li L, Liu X, Ren F: Two new ramulosin derivatives from the entomogenous fungus Truncatella angustata. Nat Prod Commun. 2015 Feb;10(2):341-4. [PubMed:25920279  ] 
  5. Shin HJ, Anh CV, Cho DY, Choi DK, Kang JS, Trinh PTH, Choi BK, Lee HS: New Polyenes from the Marine-Derived Fungus Talaromyces cyanescens with Anti-Neuroinflammatory and Cytotoxic Activities. Molecules. 2021 Feb 5;26(4):836. doi: 10.3390/molecules26040836. [PubMed:33562648  ] 
  6. Vayer M, Fang W, Guillot R, Bezzenine-Lafollee S, Bour C, Gandon V: Acid-catalysed intramolecular addition of beta-ketoesters to 1,3-dienes. Org Biomol Chem. 2017 Jan 18;15(3):584-588. doi: 10.1039/c6ob02122k. [PubMed:27775130  ] 
  7. Surup F, Kuhnert E, Liscinskij E, Stadler M: Silphiperfolene-Type Terpenoids and Other Metabolites from Cultures of the Tropical Ascomycete Hypoxylon rickii (Xylariaceae). Nat Prod Bioprospect. 2015 Jun;5(3):167-73. doi: 10.1007/s13659-015-0065-3. Epub  2015 Jun 16. [PubMed:26077652  ] 
  8. Wang J, Wang G, Zhang Y, Zheng B, Zhang C, Wang L: Isolation and identification of an endophytic fungus Pezicula sp. in Forsythia viridissima and its secondary metabolites. World J Microbiol Biotechnol. 2014 Oct;30(10):2639-44. doi:  10.1007/s11274-014-1686-0. Epub 2014 Jun 14. [PubMed:24928260  ] 
  9. LOTUS database [Link]