NP-MRD: Showing NP-Card for 8S-rosenonolactone (NP0351217)

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Record Information

Version

2.0

Created at

2025-06-28 17:19:10 UTC

Updated at

2025-06-28 20:01:38 UTC

NP-MRD ID

NP0351217

Natural Product DOI

https://doi.org/10.57994/4207

Secondary Accession Numbers

None

Natural Product Identification

Common Name

8S-rosenonolactone

Description

8S-rosenonolactone belongs to the class of organic compounds known as terpene lactones. These are prenol lipids containing a lactone ring. 8S-rosenonolactone was first documented in 2025 (PMID: 40512504). Based on a literature review very few articles have been published on 8S-rosenonolactone.

Structure

MOL SDF PDB SMILES InChI


  Mrv2104 01022310292D          

 25 28  0  0  1  0            999 V2000
    4.6882    1.7156    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9188    0.9235    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3482    0.3276    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.0341   -0.1309    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8605    0.9931    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0404    0.9034    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.2203    0.8138    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5527    1.5689    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7326    1.4792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4002    0.7242    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.8729    0.0897    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5392    1.1383    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0379    1.7936    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1663    0.4024    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5092   -0.3479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3097   -0.5477    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8879    0.0587    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.9816    0.7784    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3471    1.3057    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5468    2.1061    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7080    0.1484    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.3755   -0.6067    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1956   -0.5171    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0158   -0.4274    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8852    2.3239    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  3  2  1  6  0  0  0
  3  4  1  1  0  0  0
  3  5  1  0  0  0  0
  6  5  1  0  0  0  0
  6  7  1  6  0  0  0
  6  8  1  0  0  0  0
  8  9  1  0  0  0  0
 10  9  1  0  0  0  0
 10 11  1  1  0  0  0
 10 12  1  0  0  0  0
 12 13  1  1  0  0  0
 12 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 17 16  1  0  0  0  0
 10 17  1  0  0  0  0
 17 18  1  6  0  0  0
 18 19  1  0  0  0  0
 12 19  1  0  0  0  0
 19 20  2  0  0  0  0
 17 21  1  0  0  0  0
 21  6  1  0  0  0  0
 21 22  1  6  0  0  0
 21 23  1  0  0  0  0
 23 24  1  0  0  0  0
  3 24  1  0  0  0  0
  8 25  2  0  0  0  0
M  END


  Mrv2104 01022310292D          

 25 28  0  0  1  0            999 V2000
    4.6882    1.7156    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9188    0.9235    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3482    0.3276    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.0341   -0.1309    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8605    0.9931    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0404    0.9034    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.2203    0.8138    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5527    1.5689    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7326    1.4792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4002    0.7242    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.8729    0.0897    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5392    1.1383    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0379    1.7936    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1663    0.4024    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5092   -0.3479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3097   -0.5477    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8879    0.0587    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.9816    0.7784    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3471    1.3057    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5468    2.1061    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7080    0.1484    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.3755   -0.6067    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1956   -0.5171    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0158   -0.4274    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8852    2.3239    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  3  2  1  6  0  0  0
  3  4  1  1  0  0  0
  3  5  1  0  0  0  0
  6  5  1  0  0  0  0
  6  7  1  6  0  0  0
  6  8  1  0  0  0  0
  8  9  1  0  0  0  0
 10  9  1  0  0  0  0
 10 11  1  1  0  0  0
 10 12  1  0  0  0  0
 12 13  1  1  0  0  0
 12 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 17 16  1  0  0  0  0
 10 17  1  0  0  0  0
 17 18  1  6  0  0  0
 18 19  1  0  0  0  0
 12 19  1  0  0  0  0
 19 20  2  0  0  0  0
 17 21  1  0  0  0  0
 21  6  1  0  0  0  0
 21 22  1  6  0  0  0
 21 23  1  0  0  0  0
 23 24  1  0  0  0  0
  3 24  1  0  0  0  0
  8 25  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0351217

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H][C@@]12CC(=O)[C@@]3([H])C[C@@](C)(CC[C@@]3(C)[C@@]11CCC[C@]2(C)C(=O)O1)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-/m1/s1

> <INCHI_KEY>
HWECMADGHQKSLK-SGEYOCEGSA-N

> <FORMULA>
C20H28O3

> <MOLECULAR_WEIGHT>
316.441

> <EXACT_MASS>
316.203844762

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
51

> <JCHEM_AVERAGE_POLARIZABILITY>
35.683595186343986

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <JCHEM_LOGP>
4.132638606666667

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
19.30466995927097

> <JCHEM_PKA_STRONGEST_BASIC>
-6.954955873600421

> <JCHEM_POLAR_SURFACE_AREA>
43.370000000000005

> <JCHEM_REFRACTIVITY>
88.11099999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(1R,2R,5R,7S,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

$$$$

HEADER    PROTEIN                                 02-JAN-23   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   02-JAN-23         0                                  
HETATM    1  C   UNK     0       8.751   3.202   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       9.182   1.724   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       8.117   0.612   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       9.397  -0.244   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       7.206   1.854   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       5.675   1.686   0.000  0.00  0.00           C+0
HETATM    7  H   UNK     0       4.145   1.519   0.000  0.00  0.00           H+0
HETATM    8  C   UNK     0       4.765   2.929   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       3.234   2.761   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.614   1.352   0.000  0.00  0.00           C+0
HETATM   11  H   UNK     0       1.629   0.167   0.000  0.00  0.00           H+0
HETATM   12  C   UNK     0       1.007   2.125   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       0.071   3.348   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       0.311   0.751   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       0.951  -0.650   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       2.445  -1.022   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       3.524   0.110   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       3.699   1.453   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       2.515   2.437   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       2.887   3.931   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       5.055   0.277   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       4.434  -1.132   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       5.965  -0.965   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       7.496  -0.798   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       5.386   4.338   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    5   24                                             
CONECT    4    3                                                            
CONECT    5    3    6                                                       
CONECT    6    5    7    8   21                                             
CONECT    7    6                                                            
CONECT    8    6    9   25                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11   12   17                                             
CONECT   11   10                                                            
CONECT   12   10   13   14   19                                             
CONECT   13   12                                                            
CONECT   14   12   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   10   18   21                                             
CONECT   18   17   19                                                       
CONECT   19   18   12   20                                                  
CONECT   20   19                                                            
CONECT   21   17    6   22   23                                             
CONECT   22   21                                                            
CONECT   23   21   24                                                       
CONECT   24   23    3                                                       
CONECT   25    8                                                            
MASTER        0    0    0    0    0    0    0    0   25    0   56    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₀H₂₈O₃

Average Mass

316.4410 Da

Monoisotopic Mass

316.20384 Da

IUPAC Name

(1R,2R,5R,7S,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,7S,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 Number

Not Available

SMILES

[H][C@@]12CC(=O)[C@@]3([H])C[C@@](C)(CC[C@@]3(C)[C@@]11CCC[C@]2(C)C(=O)O1)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-/m1/s1

InChI Key

HWECMADGHQKSLK-SGEYOCEGSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
COSY NMR	[¹H, ¹H] NMR Spectrum (2D, 600 MHz, CDCl3, experimental)	156465422@qq.com	Yunna University	liangzhongdan	2025-06-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, CDCl3, experimental)	156465422@qq.com	Yunna University	liangzhongdan	2025-06-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, CDCl3, experimental)	156465422@qq.com	Yunna University	liangzhongdan	2025-06-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, CDCl3, experimental)	156465422@qq.com	Yunna University	liangzhongdan	2025-06-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, CDCl3, experimental)	156465422@qq.com	Yunna University	liangzhongdan	2025-06-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, CDCl3, experimental)	156465422@qq.com	Yunna University	liangzhongdan	2025-06-25	View Spectrum
HSQC NMR	[¹H, ¹³C] NMR Spectrum (2D, 600 MHz, CDCl3, experimental)	156465422@qq.com	Yunna University	liangzhongdan	2025-06-25	View Spectrum
NOESY NMR	[¹H, ¹H] NMR Spectrum (2D, 600 MHz, CDCl3, experimental)	156465422@qq.com	Yunna University	liangzhongdan	2025-06-25	View Spectrum
HMBC NMR	[¹H, ¹³C] NMR Spectrum (2D, 600 MHz, CDCl3, experimental)	156465422@qq.com	Yunna University	liangzhongdan	2025-06-25	View Spectrum

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Jatropha Jatropha curcas		Not Available

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as terpene lactones. These are prenol lipids containing a lactone ring.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Terpene lactones

Direct Parent

Terpene 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 Framework

Aliphatic heteropolycyclic 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	4.13	ChemAxon
pKa (Strongest Acidic)	19.3	ChemAxon
pKa (Strongest Basic)	-7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	43.37 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	88.11 m³·mol⁻¹	ChemAxon
Polarizability	35.68 Å³	ChemAxon
Number of Rings	4	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

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

101079082

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Showing NP-Card for 8S-rosenonolactone (NP0351217)

MOL for NP0351217 (8S-rosenonolactone)

3D MOL for NP0351217 (8S-rosenonolactone)

3D SDF for NP0351217 (8S-rosenonolactone)

3D-SDF for NP0351217 (8S-rosenonolactone)

PDB for NP0351217 (8S-rosenonolactone)

3D PDB for NP0351217 (8S-rosenonolactone)

SMILES for NP0351217 (8S-rosenonolactone)

INCHI for NP0351217 (8S-rosenonolactone)

Structure for NP0351217 (8S-rosenonolactone)

3D Structure for NP0351217 (8S-rosenonolactone)