NP-MRD: Showing NP-Card for Betaenone F (NP0050388)

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Record Information

Version

2.0

Created at

2022-04-27 20:56:52 UTC

Updated at

2022-04-27 20:56:52 UTC

NP-MRD ID

NP0050388

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Betaenone F

Description

3-[(1S,2R,3S,4aS,6R,8R,8aS)-2-[(2R)-butan-2-yl]-3,6-dihydroxy-1,3,6,8-tetramethyl-4-oxo-decahydronaphthalen-1-yl]-3-oxopropyl acetate belongs to the class of organic compounds known as acyloins. These are organic compounds containing an alpha hydroxy ketone. Acyloins are formally derived from reductive coupling of carboxylic acyl groups. Betaenone F is found in Phoma betae. Based on a literature review very few articles have been published on 3-[(1S,2R,3S,4aS,6R,8R,8aS)-2-[(2R)-butan-2-yl]-3,6-dihydroxy-1,3,6,8-tetramethyl-4-oxo-decahydronaphthalen-1-yl]-3-oxopropyl acetate.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652304272222562D          

 29 30  0  0  1  0            999 V2000
   -2.2534    1.4281    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.0779    1.4569    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.5151    0.7572    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3396    0.7860    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1278    0.0288    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.3033   -0.0000    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.8661    0.6996    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.1517    0.2871    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1517   -0.5379    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4372    0.6996    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2773    0.2871    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9918    0.6996    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7062    0.2871    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4207    0.6996    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7062   -0.5379    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1246    1.0613    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9160   -0.7284    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.3532   -1.4281    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1777   -1.3993    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.5650   -0.6708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2352   -2.2223    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8921   -1.8118    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1407   -1.0106    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0779    2.2819    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7619    1.9182    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8163    2.1277    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.9918    2.0989    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2036    2.8561    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7664    3.5558    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  2  0  0  0  0
  5  3  1  6  0  0  0
  6  5  1  1  0  0  0
  6  7  1  0  0  0  0
  1  7  1  0  0  0  0
  7  8  1  1  0  0  0
  8  9  2  0  0  0  0
  8 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 13 15  1  0  0  0  0
  7 16  1  6  0  0  0
  6 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
  5 20  1  0  0  0  0
 19 21  1  1  0  0  0
 19 22  1  6  0  0  0
 17 23  1  6  0  0  0
  2 24  1  1  0  0  0
  2 25  1  6  0  0  0
  1 26  1  6  0  0  0
 26 27  1  1  0  0  0
 26 28  1  0  0  0  0
 28 29  1  0  0  0  0
M  END


  Mrv1652304272222562D          

 29 30  0  0  1  0            999 V2000
   -2.2534    1.4281    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.0779    1.4569    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.5151    0.7572    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3396    0.7860    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1278    0.0288    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.3033   -0.0000    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.8661    0.6996    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.1517    0.2871    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1517   -0.5379    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4372    0.6996    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2773    0.2871    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9918    0.6996    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7062    0.2871    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4207    0.6996    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7062   -0.5379    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1246    1.0613    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9160   -0.7284    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.3532   -1.4281    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1777   -1.3993    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.5650   -0.6708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2352   -2.2223    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8921   -1.8118    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1407   -1.0106    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0779    2.2819    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7619    1.9182    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8163    2.1277    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.9918    2.0989    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2036    2.8561    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7664    3.5558    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  2  0  0  0  0
  5  3  1  6  0  0  0
  6  5  1  1  0  0  0
  6  7  1  0  0  0  0
  1  7  1  0  0  0  0
  7  8  1  1  0  0  0
  8  9  2  0  0  0  0
  8 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 13 15  1  0  0  0  0
  7 16  1  6  0  0  0
  6 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
  5 20  1  0  0  0  0
 19 21  1  1  0  0  0
 19 22  1  6  0  0  0
 17 23  1  6  0  0  0
  2 24  1  1  0  0  0
  2 25  1  6  0  0  0
  1 26  1  6  0  0  0
 26 27  1  1  0  0  0
 26 28  1  0  0  0  0
 28 29  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0050388

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC[C@@H](C)[C@H]1[C@](C)(O)C(=O)[C@H]2C[C@](C)(O)C[C@@H](C)[C@@H]2[C@]1(C)C(=O)CCOC(C)=O

> <INCHI_IDENTIFIER>
InChI=1S/C23H38O6/c1-8-13(2)19-22(6,17(25)9-10-29-15(4)24)18-14(3)11-21(5,27)12-16(18)20(26)23(19,7)28/h13-14,16,18-19,27-28H,8-12H2,1-7H3/t13-,14-,16+,18+,19-,21-,22+,23+/m1/s1

> <INCHI_KEY>
FLFBDTRJVACJLZ-UTYOWGLHSA-N

> <FORMULA>
C23H38O6

> <MOLECULAR_WEIGHT>
410.551

> <EXACT_MASS>
410.266838944

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
67

> <JCHEM_AVERAGE_POLARIZABILITY>
46.14826016964092

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
3-[(1S,2R,3S,4aS,6R,8R,8aS)-2-[(2R)-butan-2-yl]-3,6-dihydroxy-1,3,6,8-tetramethyl-4-oxo-decahydronaphthalen-1-yl]-3-oxopropyl acetate

> <ALOGPS_LOGP>
2.95

> <JCHEM_LOGP>
2.996591961000002

> <ALOGPS_LOGS>
-4.13

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.992144785735924

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.997316048133477

> <JCHEM_PKA_STRONGEST_BASIC>
-2.7876076353694073

> <JCHEM_POLAR_SURFACE_AREA>
100.9

> <JCHEM_REFRACTIVITY>
109.8994

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.04e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3-[(1S,2R,3S,4aS,6R,8R,8aS)-2-[(2R)-butan-2-yl]-3,6-dihydroxy-1,3,6,8-tetramethyl-4-oxo-hexahydronaphthalen-1-yl]-3-oxopropyl acetate

> <JCHEM_VEBER_RULE>
0

$$$$

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      -4.206   2.666   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -5.745   2.719   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -6.562   1.413   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0      -8.101   1.467   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0      -5.839   0.054   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -4.300  -0.000   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -3.483   1.306   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -2.150   0.536   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0      -2.150  -1.004   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0      -0.816   1.306   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.518   0.536   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       1.851   1.306   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       3.185   0.536   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       4.519   1.306   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       3.185  -1.004   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -2.099   1.981   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -3.577  -1.360   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -4.393  -2.666   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -5.932  -2.612   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -6.655  -1.252   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      -6.039  -4.148   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0      -7.265  -3.382   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -2.129  -1.886   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0      -5.745   4.259   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0      -7.022   3.581   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      -3.390   3.972   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      -1.851   3.918   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      -4.113   5.331   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      -3.297   6.637   0.000  0.00  0.00           C+0
CONECT    1    2    7   26                                                  
CONECT    2    1    3   24   25                                             
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6   20                                                  
CONECT    6    5    7   17                                                  
CONECT    7    6    1    8   16                                             
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13                                                            
CONECT   16    7                                                            
CONECT   17    6   18   23                                                  
CONECT   18   17   19                                                       
CONECT   19   18   20   21   22                                             
CONECT   20   19    5                                                       
CONECT   21   19                                                            
CONECT   22   19                                                            
CONECT   23   17                                                            
CONECT   24    2                                                            
CONECT   25    2                                                            
CONECT   26    1   27   28                                                  
CONECT   27   26                                                            
CONECT   28   26   29                                                       
CONECT   29   28                                                            
MASTER        0    0    0    0    0    0    0    0   29    0   60    0
END

View in JSmol

Synonyms

Value	Source
3-[(1S,2R,3S,4AS,6R,8R,8as)-2-[(2R)-butan-2-yl]-3,6-dihydroxy-1,3,6,8-tetramethyl-4-oxo-decahydronaphthalen-1-yl]-3-oxopropyl acetic acid	Generator

Chemical Formula

C₂₃H₃₈O₆

Average Mass

410.5510 Da

Monoisotopic Mass

410.26684 Da

IUPAC Name

3-[(1S,2R,3S,4aS,6R,8R,8aS)-2-[(2R)-butan-2-yl]-3,6-dihydroxy-1,3,6,8-tetramethyl-4-oxo-decahydronaphthalen-1-yl]-3-oxopropyl acetate

Traditional Name

3-[(1S,2R,3S,4aS,6R,8R,8aS)-2-[(2R)-butan-2-yl]-3,6-dihydroxy-1,3,6,8-tetramethyl-4-oxo-hexahydronaphthalen-1-yl]-3-oxopropyl acetate

CAS Registry Number

Not Available

SMILES

CC[C@@H](C)[C@H]1[C@](C)(O)C(=O)[C@H]2C[C@](C)(O)C[C@@H](C)[C@@H]2[C@]1(C)C(=O)CCOC(C)=O

InChI Identifier

InChI=1S/C23H38O6/c1-8-13(2)19-22(6,17(25)9-10-29-15(4)24)18-14(3)11-21(5,27)12-16(18)20(26)23(19,7)28/h13-14,16,18-19,27-28H,8-12H2,1-7H3/t13-,14-,16+,18+,19-,21-,22+,23+/m1/s1

InChI Key

FLFBDTRJVACJLZ-UTYOWGLHSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Phoma betae	Fungi	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as acyloins. These are organic compounds containing an alpha hydroxy ketone. Acyloins are formally derived from reductive coupling of carboxylic acyl groups.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbonyl compounds

Direct Parent

Acyloins

Alternative Parents

Substituents

Acyloin
Tertiary alcohol
Cyclic alcohol
Ketone
Carboxylic acid ester
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Organic oxide
Hydrocarbon derivative
Alcohol
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic 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	2.95	ALOGPS
logP	3	ChemAxon
logS	-4.1	ALOGPS
pKa (Strongest Acidic)	13	ChemAxon
pKa (Strongest Basic)	-2.8	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	100.9 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	109.9 m³·mol⁻¹	ChemAxon
Polarizability	46.15 Å³	ChemAxon
Number of Rings	2	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

163065570

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Betaenone F (NP0050388)

MOL for NP0050388 (Betaenone F)

3D MOL for NP0050388 (Betaenone F)

3D SDF for NP0050388 (Betaenone F)

3D-SDF for NP0050388 (Betaenone F)

PDB for NP0050388 (Betaenone F)

3D PDB for NP0050388 (Betaenone F)

SMILES for NP0050388 (Betaenone F)

INCHI for NP0050388 (Betaenone F)

Structure for NP0050388 (Betaenone F)

3D Structure for NP0050388 (Betaenone F)