Np mrd loader

Showing NP-Card for Rosenonolactone (NP0050552)

Jump To Section:
IdentificationSpectraBioTaxonomyChemoTaxonomyPhysical propertiesLinksReferencesXML
Record Information
Version2.0
Created at2022-04-27 21:56:47 UTC
Updated at2022-04-27 21:56:47 UTC
NP-MRD IDNP0050552
Secondary Accession NumbersNone
Natural Product Identification
Common NameRosenonolactone
DescriptionRosenonolactone belongs to the class of organic compounds known as terpene lactones. These are prenol lipids containing a lactone ring. Rosenonolactone is found in Cyperus rotundus, Duranta erecta, Duranta repens, Holarrhena floribunda and Trichothecium roseum. Rosenonolactone was first documented in 2008 (PMID: 18923338). Based on a literature review a small amount of articles have been published on Rosenonolactone (PMID: 26136058) (PMID: 25850378).
Structure
Thumb
MOLSDFPDBSMILESInChI

MOL for NP0050552 (Rosenonolactone)


  Mrv1652304272223562D          

 23 26  0  0  1  0            999 V2000
    0.2203    0.8899    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1226    0.1395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2502   -0.5964    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.1112   -0.1822    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.5989    0.4832    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.0207    1.0897    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4190    0.3936    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.7514   -0.3615    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.2638   -1.0269    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5962   -1.7819    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4436   -0.9373    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5716   -0.4511    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0592    0.2143    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.7268    0.9694    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9067    1.0590    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7413   -0.2498    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4843    0.1088    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8254    0.5202    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0866    1.1486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6926   -0.2364    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0581   -0.7637    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2579   -1.5642    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2510   -1.2516    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  1  6  1  0  0  0  0
  5  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  1  0  0  0
  9 10  2  0  0  0  0
  9 11  1  0  0  0  0
  4 11  1  1  0  0  0
  8 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
  7 15  1  0  0  0  0
 13 16  1  1  0  0  0
 16 17  2  0  0  0  0
 13 18  1  6  0  0  0
  7 19  1  1  0  0  0
  5 20  1  1  0  0  0
 20 21  1  0  0  0  0
  3 21  1  0  0  0  0
 21 22  2  0  0  0  0
  3 23  1  6  0  0  0
M  END
Download

3D MOL for NP0050552 (Rosenonolactone)

Download
3D SDF for NP0050552 (Rosenonolactone)

  Mrv1652304272223562D          

 23 26  0  0  1  0            999 V2000
    0.2203    0.8899    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1226    0.1395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2502   -0.5964    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.1112   -0.1822    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.5989    0.4832    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.0207    1.0897    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4190    0.3936    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.7514   -0.3615    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.2638   -1.0269    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5962   -1.7819    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4436   -0.9373    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5716   -0.4511    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0592    0.2143    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.7268    0.9694    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9067    1.0590    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7413   -0.2498    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4843    0.1088    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8254    0.5202    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0866    1.1486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6926   -0.2364    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0581   -0.7637    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2579   -1.5642    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2510   -1.2516    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  1  6  1  0  0  0  0
  5  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  1  0  0  0
  9 10  2  0  0  0  0
  9 11  1  0  0  0  0
  4 11  1  1  0  0  0
  8 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
  7 15  1  0  0  0  0
 13 16  1  1  0  0  0
 16 17  2  0  0  0  0
 13 18  1  6  0  0  0
  7 19  1  1  0  0  0
  5 20  1  1  0  0  0
 20 21  1  0  0  0  0
  3 21  1  0  0  0  0
 21 22  2  0  0  0  0
  3 23  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0050552

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@@]12CCC[C@@]3(OC1=O)[C@H]2CC(=O)[C@@H]1C[C@@](C)(CC[C@@]31C)C=C

> <INCHI_IDENTIFIER>
InChI=1S/C20H28O3/c1-5-17(2)9-10-19(4)13(12-17)14(21)11-15-18(3)7-6-8-20(15,19)23-16(18)22/h5,13,15H,1,6-12H2,2-4H3/t13-,15-,17+,18-,19+,20+/m0/s1

> <INCHI_KEY>
HWECMADGHQKSLK-BWXAORSUSA-N

> <FORMULA>
C20H28O3

> <MOLECULAR_WEIGHT>
316.441

> <EXACT_MASS>
316.203844762

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
51

> <JCHEM_AVERAGE_POLARIZABILITY>
35.881336395407054

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1R,2R,5R,7R,10S,11S)-5-ethenyl-2,5,11-trimethyl-15-oxatetracyclo[9.3.2.0^{1,10}.0^{2,7}]hexadecane-8,16-dione

> <ALOGPS_LOGP>
3.63

> <JCHEM_LOGP>
4.132638606666667

> <ALOGPS_LOGS>
-5.30

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
17.337845829927456

> <JCHEM_PKA_STRONGEST_BASIC>
-6.954955873600421

> <JCHEM_POLAR_SURFACE_AREA>
43.370000000000005

> <JCHEM_REFRACTIVITY>
88.11099999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.57e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1R,2R,5R,7R,10S,11S)-5-ethenyl-2,5,11-trimethyl-15-oxatetracyclo[9.3.2.0^{1,10}.0^{2,7}]hexadecane-8,16-dione

> <JCHEM_VEBER_RULE>
0

$$$$

Download
3D-SDF for NP0050552 (Rosenonolactone)
Download
PDB for NP0050552 (Rosenonolactone)
HEADER    PROTEIN                                 27-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-APR-22         0                                  
HETATM    1  C   UNK     0       0.411   1.661   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -0.229   0.260   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.467  -1.113   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.074  -0.340   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.985   0.902   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.905   2.034   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.515   0.735   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       5.136  -0.675   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.226  -1.917   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       4.846  -3.326   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       2.695  -1.750   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       6.667  -0.842   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       7.577   0.400   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       6.957   1.810   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       5.426   1.977   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       8.850  -0.466   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      10.237   0.203   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       9.007   0.971   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       3.895   2.144   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       3.160  -0.441   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       1.975  -1.426   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       2.348  -2.920   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0      -0.469  -2.336   0.000  0.00  0.00           C+0
CONECT    1    2    6                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4   21   23                                             
CONECT    4    3    5   11                                                  
CONECT    5    4    6    7   20                                             
CONECT    6    5    1                                                       
CONECT    7    5    8   15   19                                             
CONECT    8    7    9   12                                                  
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9    4                                                       
CONECT   12    8   13                                                       
CONECT   13   12   14   16   18                                             
CONECT   14   13   15                                                       
CONECT   15   14    7                                                       
CONECT   16   13   17                                                       
CONECT   17   16                                                            
CONECT   18   13                                                            
CONECT   19    7                                                            
CONECT   20    5   21                                                       
CONECT   21   20    3   22                                                  
CONECT   22   21                                                            
CONECT   23    3                                                            
MASTER        0    0    0    0    0    0    0    0   23    0   52    0
END

Download
3D PDB for NP0050552 (Rosenonolactone)
Download
SMILES for NP0050552 (Rosenonolactone)
C[C@@]12CCC[C@@]3(OC1=O)[C@H]2CC(=O)[C@@H]1C[C@@](C)(CC[C@@]31C)C=C
Download
INCHI for NP0050552 (Rosenonolactone)
InChI=1S/C20H28O3/c1-5-17(2)9-10-19(4)13(12-17)14(21)11-15-18(3)7-6-8-20(15,19)23-16(18)22/h5,13,15H,1,6-12H2,2-4H3/t13-,15-,17+,18-,19+,20+/m0/s1
Download
View in JSmol
SynonymsNot Available
Chemical FormulaC20H28O3
Average Mass316.4410 Da
Monoisotopic Mass316.20384 Da
IUPAC Name(1R,2R,5R,7R,10S,11S)-5-ethenyl-2,5,11-trimethyl-15-oxatetracyclo[9.3.2.0^{1,10}.0^{2,7}]hexadecane-8,16-dione
Traditional Name(1R,2R,5R,7R,10S,11S)-5-ethenyl-2,5,11-trimethyl-15-oxatetracyclo[9.3.2.0^{1,10}.0^{2,7}]hexadecane-8,16-dione
CAS Registry NumberNot Available
SMILES
C[C@@]12CCC[C@@]3(OC1=O)[C@H]2CC(=O)[C@@H]1C[C@@](C)(CC[C@@]31C)C=C
InChI Identifier
InChI=1S/C20H28O3/c1-5-17(2)9-10-19(4)13(12-17)14(21)11-15-18(3)7-6-8-20(15,19)23-16(18)22/h5,13,15H,1,6-12H2,2-4H3/t13-,15-,17+,18-,19+,20+/m0/s1
InChI KeyHWECMADGHQKSLK-BWXAORSUSA-N
Experimental Spectra
Not Available
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Cyperus rotundusLOTUS Database
Duranta erectaLOTUS Database
Duranta repensPlant
Holarrhena floribundaPlant
Trichothecium roseumFungi
Chemical Taxonomy
Description Belongs to the class of organic compounds known as terpene lactones. These are prenol lipids containing a lactone ring.
KingdomOrganic compounds  
Super ClassLipids and lipid-like molecules  
ClassPrenol lipids  
Sub ClassTerpene lactones  
Direct ParentTerpene lactones  
Alternative Parents
Substituents
  • Terpene lactone
    • 

  • Sesquiterpenoid
    • 

  • Naphthofuran
    • 

  • Caprolactone
    • 

  • Oxepane
    • 

  • Gamma butyrolactone
    • 

  • Oxolane
    • 

  • Carboxylic acid ester
    • 

  • Ketone
    • 

  • Lactone
    • 

  • Carboxylic acid derivative
    • 

  • Oxacycle
    • 

  • Organoheterocyclic compound
    • 

  • Monocarboxylic acid or derivatives
    • 

  • Hydrocarbon derivative
    • 

  • Organic oxide
    • 

  • Organic oxygen compound
    • 

  • 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
logP3.63ALOGPS
logP4.13ChemAxon
logS-5.3ALOGPS
pKa (Strongest Acidic)17.34ChemAxon
pKa (Strongest Basic)-7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area43.37 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity88.11 m³·mol⁻¹ChemAxon
Polarizability35.88 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDC00000892  
Chemspider ID9898025  
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound11723309  
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. Wang SR, Zhang L, Chen HP, Li ZH, Dong ZJ, Wei K, Liu JK: Four new spiroaxane sesquiterpenes and one new rosenonolactone derivative from cultures of Basidiomycete Trametes versicolor. Fitoterapia. 2015 Sep;105:127-31. doi: 10.1016/j.fitote.2015.06.017. Epub 2015 Jun 30. [PubMed:26136058  ] 
  2. Wang Y, Zhang L, Wang F, Li ZH, Dong ZJ, Liu JK: New Diterpenes from Cultures of the Fungus Engleromyces goetzii and Their CETP Inhibitory Activity. Nat Prod Bioprospect. 2015 Apr 8. doi: 10.1007/s13659-015-0055-5. [PubMed:25850378  ] 
  3. Xu Y, Zhang HW, Yu CY, Lu Y, Chang Y, Zou ZM: Norcyperone, a novel skeleton norsesquiterpene from Cyperus rotundus L. Molecules. 2008 Oct 10;13(10):2474-81. doi: 10.3390/molecules13102474. [PubMed:18923338  ]