NP-MRD: Showing NP-Card for Dehydrojuvabione (NP0051793)

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Record Information

Version

2.0

Created at

2022-04-27 23:01:30 UTC

Updated at

2022-04-27 23:01:31 UTC

NP-MRD ID

NP0051793

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Dehydrojuvabione

Description

Dehydrojuvabione belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units. Dehydrojuvabione is found in Abies balsamea . Dehydrojuvabione was first documented in 2001 (PMID: 11452590). Dehydrojuvabione is an extremely weak basic (essentially neutral) compound (based on its pKa) (PMID: 22799597).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 43 43  0  0  0  0  0  0  0  0999 V2000
   -7.3111    0.8506   -0.5914 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8830    0.9339   -0.5144 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1019   -0.1414   -0.1030 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7531   -1.2021    0.1981 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6604   -0.0949   -0.0120 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0058    0.9801   -0.3209 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5275    1.1166   -0.2537 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8286   -0.1466    0.1259 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.5755   -0.2432   -0.3822 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.1565   -1.5690    0.0991 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4203    0.8270    0.2894 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8049    0.6382   -0.2824 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9331    0.6460   -1.5303 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9390    0.4512    0.6058 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1594    0.2786    0.1720 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2680    0.0911    1.1541 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4297    0.2797   -1.2898 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6502   -1.3129   -0.4092 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9290   -1.2973    0.4466 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6757    1.8976   -0.6965 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7563    0.4146    0.3138 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6236    0.2804   -1.4743 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5589    1.8452   -0.6522 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1885    1.5394   -1.2187 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3323    1.8901    0.5296 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8618   -0.2295    1.2453 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5949   -0.1537   -1.4613 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1604   -1.4252    0.5824 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2382   -2.2947   -0.7460 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5042   -2.0387    0.8661 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4605    0.6446    1.3794 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0499    1.8415    0.0091 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7736    0.4555    1.6892 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8525    1.0107    1.3241 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9686   -0.6943    0.7497 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8794   -0.2529    2.1333 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8933   -0.5340   -1.8336 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5188    0.1456   -1.4954 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1628    1.2740   -1.6992 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9241   -1.0493   -1.4606 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1254   -2.2668   -0.3312 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5535   -1.1613    1.4990 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4930   -2.2244    0.3989 H   0  0  0  0  0  0  0  0  0  0  0  0
  8 18  1  0
 18 19  1  0
 19  5  1  0
  5  6  2  0
  6  7  1  0
  5  3  1  0
  3  4  2  0
  3  2  1  0
  2  1  1  0
  8  9  1  0
  9 10  1  0
  9 11  1  0
 11 12  1  0
 12 13  2  0
 12 14  1  0
 14 15  2  3
 15 16  1  0
 15 17  1  0
  7  8  1  0
  8 26  1  1
 18 40  1  0
 18 41  1  0
 19 42  1  0
 19 43  1  0
  6 23  1  0
  7 24  1  0
  7 25  1  0
  1 20  1  0
  1 21  1  0
  1 22  1  0
  9 27  1  6
 10 28  1  0
 10 29  1  0
 10 30  1  0
 11 31  1  0
 11 32  1  0
 14 33  1  0
 16 34  1  0
 16 35  1  0
 16 36  1  0
 17 37  1  0
 17 38  1  0
 17 39  1  0
M  END


  Mrv1652309272006412D          

 20 20  0  0  0  0            999 V2000
10021.163510021.6409    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
10021.880310021.2289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10022.593010021.6409    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10023.305510021.2289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10024.020310021.6409    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10024.732910021.2289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10024.020310022.4648    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10022.593010022.4648    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10021.163510022.4648    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10018.310110019.9932    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10017.596610020.4061    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10016.881010019.9932    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10018.310110019.1692    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10021.163510020.8170    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
10019.737610021.6441    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10019.021610021.2307    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10019.737610019.9907    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10020.453610020.4039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10020.453610021.2307    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
10019.021610020.4039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  9  1  6  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  3  8  2  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  5  7  1  0  0  0  0
 10 11  1  0  0  0  0
 10 13  2  0  0  0  0
 11 12  1  0  0  0  0
 15 16  1  0  0  0  0
 15 19  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 16 20  1  0  0  0  0
 20 17  2  0  0  0  0
  1 19  1  0  0  0  0
 19 14  1  6  0  0  0
 20 10  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0051793

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H][C@]1(CCC(=CC1)C(=O)OC)[C@H](C)CC(=O)C=C(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C16H24O3/c1-11(2)9-15(17)10-12(3)13-5-7-14(8-6-13)16(18)19-4/h7,9,12-13H,5-6,8,10H2,1-4H3/t12-,13+/m1/s1

> <INCHI_KEY>
DEMNMQDWPCIOLA-OLZOCXBDSA-N

> <FORMULA>
C16H24O3

> <MOLECULAR_WEIGHT>
264.365

> <EXACT_MASS>
264.172544633

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
43

> <JCHEM_AVERAGE_POLARIZABILITY>
30.499658691187804

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
methyl (4R)-4-[(2R)-6-methyl-4-oxohept-5-en-2-yl]cyclohex-1-ene-1-carboxylate

> <ALOGPS_LOGP>
3.71

> <JCHEM_LOGP>
3.978620147

> <ALOGPS_LOGS>
-4.12

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-4.359227589380237

> <JCHEM_POLAR_SURFACE_AREA>
43.370000000000005

> <JCHEM_REFRACTIVITY>
77.60979999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.99e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
dehydrojuvabione

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 27-SEP-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-SEP-20         0                                  
HETATM    1  C   UNK     0    8706.1728707.063   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0    8707.5108706.294   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0    8708.8408707.063   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0    8710.1708706.294   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0    8711.5058707.063   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0    8712.8358706.294   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0    8711.5058708.601   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0    8708.8408708.601   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0    8706.1728708.601   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0    8700.8458703.987   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0    8699.5148704.758   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0    8698.1788703.987   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0    8700.8458702.449   0.000  0.00  0.00           O+0
HETATM   14  H   UNK     0    8706.1728705.525   0.000  0.00  0.00           H+0
HETATM   15  C   UNK     0    8703.5108707.069   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0    8702.1748706.297   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0    8703.5108703.983   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0    8704.8478704.754   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0    8704.8478706.297   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0    8702.1748704.754   0.000  0.00  0.00           C+0
CONECT    1    2    9   19                                                  
CONECT    2    1    3                                                       
CONECT    3    2    4    8                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5                                                            
CONECT    8    3                                                            
CONECT    9    1                                                            
CONECT   10   11   13   20                                                  
CONECT   11   10   12                                                       
CONECT   12   11                                                            
CONECT   13   10                                                            
CONECT   14   19                                                            
CONECT   15   16   19                                                       
CONECT   16   15   20                                                       
CONECT   17   18   20                                                       
CONECT   18   17   19                                                       
CONECT   19   15   18    1   14                                             
CONECT   20   16   17   10                                                  
MASTER        0    0    0    0    0    0    0    0   20    0   40    0
END

View in JSmol

Synonyms

Value	Source
(4R)-4-[(1R)-1,5-Dimethyl-3-oxo-4-hexenyl]-1-cyclohexene-1-carboxylic acid methyl ester	Kegg
(4R)-4-[(1R)-1,5-Dimethyl-3-oxo-4-hexenyl]-1-cyclohexene-1-carboxylate methyl ester	Generator
(+)-delta4'-Dehydrojuvabione	PhytoBank
(+)-Δ4'-Dehydrojuvabione	PhytoBank
(+)-Δ4’-Dehydrojuvabione	PhytoBank
4'-Dehydrojuvabione	PhytoBank
4’-Dehydrojuvabione	PhytoBank

Chemical Formula

C₁₆H₂₄O₃

Average Mass

264.3650 Da

Monoisotopic Mass

264.17254 Da

IUPAC Name

methyl (4R)-4-[(2R)-6-methyl-4-oxohept-5-en-2-yl]cyclohex-1-ene-1-carboxylate

Traditional Name

dehydrojuvabione

CAS Registry Number

Not Available

SMILES

[H][C@]1(CCC(=CC1)C(=O)OC)[C@H](C)CC(=O)C=C(C)C

InChI Identifier

InChI=1S/C16H24O3/c1-11(2)9-15(17)10-12(3)13-5-7-14(8-6-13)16(18)19-4/h7,9,12-13H,5-6,8,10H2,1-4H3/t12-,13+/m1/s1

InChI Key

DEMNMQDWPCIOLA-OLZOCXBDSA-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, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, 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
Abies balsamea	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Sesquiterpenoids

Direct Parent

Sesquiterpenoids

Alternative Parents

Substituents

Sesquiterpenoid
Bisabolane sesquiterpenoid
Acryloyl-group
Enone
Methyl ester
Enoate ester
Alpha,beta-unsaturated carboxylic ester
Alpha,beta-unsaturated ketone
Ketone
Carboxylic acid ester
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Organic oxygen compound
Organooxygen compound
Organic oxide
Carbonyl group
Hydrocarbon derivative
Aliphatic homomonocyclic compound

Molecular Framework

Aliphatic homomonocyclic compounds

External Descriptors

sesquiterpenoid (CHEBI:4365 )
Bisabolanes (C09657 )

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	3.71	ALOGPS
logP	3.98	ChemAxon
logS	-4.1	ALOGPS
pKa (Strongest Basic)	-4.4	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	6	ChemAxon
Refractivity	77.61 m³·mol⁻¹	ChemAxon
Polarizability	30.5 Å³	ChemAxon
Number of Rings	1	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

C00003126

Chemspider ID

76890

KEGG Compound ID

C09657

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

85259

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Awasthi P, Sharma P: In silico screening of the juvabione category of juvenile hormone analogues with juvenile hormone binding protein of Galleria mellonella--a docking study. SAR QSAR Environ Res. 2012 Oct;23(7-8):607-25. doi: 10.1080/1062936X.2012.665384. Epub 2012 Jul 17. [PubMed:22799597 ]
Fine PM, Cass GR, Simoneit BR: Chemical characterization of fine particle emissions from fireplace combustion of woods grown in the northeastern United States. Environ Sci Technol. 2001 Jul 1;35(13):2665-75. doi: 10.1021/es001466k. [PubMed:11452590 ]

Showing NP-Card for Dehydrojuvabione (NP0051793)

MOL for NP0051793 (Dehydrojuvabione)

3D MOL for NP0051793 (Dehydrojuvabione)

3D SDF for NP0051793 (Dehydrojuvabione)

3D-SDF for NP0051793 (Dehydrojuvabione)

PDB for NP0051793 (Dehydrojuvabione)

3D PDB for NP0051793 (Dehydrojuvabione)

SMILES for NP0051793 (Dehydrojuvabione)

INCHI for NP0051793 (Dehydrojuvabione)

Structure for NP0051793 (Dehydrojuvabione)

3D Structure for NP0051793 (Dehydrojuvabione)