NP-MRD: Showing NP-Card for Semialactone (NP0139216)

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Record Information

Version

2.0

Created at

2022-06-29 19:44:24 UTC

Updated at

2022-06-29 19:44:25 UTC

NP-MRD ID

NP0139216

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Semialactone

Description

Semialactone belongs to the class of organic compounds known as triterpenoids. These are terpene molecules containing six isoprene units. Semialactone is found in Brucea javanica. Semialactone was first documented in 2001 (PMID: 11515571). Based on a literature review very few articles have been published on Semialactone.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652306292221442D          

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M  END

     RDKit          3D

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M  END


  Mrv1652306292221442D          

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 22 23  1  0  0  0  0
 18 23  1  0  0  0  0
 23 24  1  6  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 22 27  1  0  0  0  0
 27 28  1  0  0  0  0
 27 29  1  0  0  0  0
 26 30  1  0  0  0  0
 30 31  1  0  0  0  0
 23 31  1  0  0  0  0
 26 32  1  1  0  0  0
 19 33  1  1  0  0  0
 14 34  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0139216

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1=CC[C@H](OC1=O)C(=C)[C@H]1CC[C@]2(C)[C@@H]1CC[C@H]1[C@@]2(C)CC[C@H]2C(C)(C)[C@]3(O)CC[C@]12CO3

> <INCHI_IDENTIFIER>
InChI=1S/C30H44O4/c1-18-7-9-22(34-25(18)31)19(2)20-11-13-27(5)21(20)8-10-24-28(27,6)14-12-23-26(3,4)30(32)16-15-29(23,24)17-33-30/h7,20-24,32H,2,8-17H2,1,3-6H3/t20-,21-,22+,23+,24+,27-,28-,29-,30+/m1/s1

> <INCHI_KEY>
GNMZYIRHZHRDGC-GJHSOGOJSA-N

> <FORMULA>
C30H44O4

> <MOLECULAR_WEIGHT>
468.678

> <EXACT_MASS>
468.323959897

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
78

> <JCHEM_AVERAGE_POLARIZABILITY>
54.27596853981865

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(6S)-6-{1-[(1S,2S,5R,6S,9R,10R,13R,15S)-15-hydroxy-9,10,14,14-tetramethyl-16-oxapentacyclo[13.2.2.0^{1,13}.0^{2,10}.0^{5,9}]nonadecan-6-yl]ethenyl}-3-methyl-5,6-dihydro-2H-pyran-2-one

> <ALOGPS_LOGP>
5.17

> <JCHEM_LOGP>
6.129496913999999

> <ALOGPS_LOGS>
-6.34

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.685010913937782

> <JCHEM_PKA_STRONGEST_BASIC>
-4.248776226243614

> <JCHEM_POLAR_SURFACE_AREA>
55.760000000000005

> <JCHEM_REFRACTIVITY>
133.3216

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.15e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(6S)-6-{1-[(1S,2S,5R,6S,9R,10R,13R,15S)-15-hydroxy-9,10,14,14-tetramethyl-16-oxapentacyclo[13.2.2.0^{1,13}.0^{2,10}.0^{5,9}]nonadecan-6-yl]ethenyl}-3-methyl-5,6-dihydropyran-2-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 29-JUN-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   29-JUN-22         0                                  
HETATM    1  C   UNK     0      18.179   2.531   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      16.640   2.505   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      15.893   1.158   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      14.353   1.132   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      13.560   2.453   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0      14.307   3.799   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0      15.847   3.825   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0      16.594   5.172   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0      12.020   2.426   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      11.228   3.747   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      11.273   1.080   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      11.924  -0.316   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      10.797  -1.366   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       9.450  -0.619   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       9.745   0.893   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       8.583   1.903   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       7.126   1.403   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       6.832  -0.109   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       7.994  -1.120   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       7.360  -2.567   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       5.809  -2.807   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       4.800  -1.534   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       5.179   0.066   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       3.836   1.282   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       2.281   1.392   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       2.212  -0.168   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       3.167  -1.434   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       1.906  -2.317   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       3.128  -2.973   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0       3.752   0.212   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0       4.937   1.472   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0       0.742  -0.625   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0       9.037  -2.252   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       9.796  -2.120   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    7                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6    9                                                  
CONECT    6    5    7                                                       
CONECT    7    6    2    8                                                  
CONECT    8    7                                                            
CONECT    9    5   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12   15                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15   19   34                                             
CONECT   15   14   11   16                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19   23                                                  
CONECT   19   18   14   20   33                                             
CONECT   20   19   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   23   27                                                  
CONECT   23   22   18   24   31                                             
CONECT   24   23   25                                                       
CONECT   25   24   26                                                       
CONECT   26   25   27   30   32                                             
CONECT   27   26   22   28   29                                             
CONECT   28   27                                                            
CONECT   29   27                                                            
CONECT   30   26   31                                                       
CONECT   31   30   23                                                       
CONECT   32   26                                                            
CONECT   33   19                                                            
CONECT   34   14                                                            
MASTER        0    0    0    0    0    0    0    0   34    0   78    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₃₀H₄₄O₄

Average Mass

468.6780 Da

Monoisotopic Mass

468.32396 Da

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

CC1=CC[C@H](OC1=O)C(=C)[C@H]1CC[C@]2(C)[C@@H]1CC[C@H]1[C@@]2(C)CC[C@H]2C(C)(C)[C@]3(O)CC[C@]12CO3

InChI Identifier

InChI=1S/C30H44O4/c1-18-7-9-22(34-25(18)31)19(2)20-11-13-27(5)21(20)8-10-24-28(27,6)14-12-23-26(3,4)30(32)16-15-29(23,24)17-33-30/h7,20-24,32H,2,8-17H2,1,3-6H3/t20-,21-,22+,23+,24+,27-,28-,29-,30+/m1/s1

InChI Key

GNMZYIRHZHRDGC-GJHSOGOJSA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Brucea javanica	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as triterpenoids. These are terpene molecules containing six isoprene units.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Triterpenoids

Direct Parent

Triterpenoids

Alternative Parents

Substituents

Triterpenoid
Naphthopyran
Naphthalene
Dihydropyranone
Oxane
Pyran
Cyclic alcohol
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Lactone
Hemiacetal
Carboxylic acid ester
Oxacycle
Monocarboxylic acid or derivatives
Organoheterocyclic compound
Carboxylic acid derivative
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Carbonyl group
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

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

34966918

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

91895428

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Lee IS, Oh SR, Ahn KS, Lee HK: Semialactone, isofouquierone peroxide and fouquierone, three new dammarane triterpenes from Rhus javanica. Chem Pharm Bull (Tokyo). 2001 Aug;49(8):1024-6. doi: 10.1248/cpb.49.1024. [PubMed:11515571 ]

Showing NP-Card for Semialactone (NP0139216)

MOL for NP0139216 (Semialactone)

3D MOL for NP0139216 (Semialactone)

3D SDF for NP0139216 (Semialactone)

3D-SDF for NP0139216 (Semialactone)

PDB for NP0139216 (Semialactone)

3D PDB for NP0139216 (Semialactone)

SMILES for NP0139216 (Semialactone)

INCHI for NP0139216 (Semialactone)

Structure for NP0139216 (Semialactone)

3D Structure for NP0139216 (Semialactone)