NP-MRD: Showing NP-Card for 5,14-dihydroxy-2,6,10,14-tetramethylhexadeca-2,6,15-triene-4,12-dione (NP0218327)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-09-05 18:57:17 UTC

Updated at

2022-09-05 18:57:17 UTC

NP-MRD ID

NP0218327

Secondary Accession Numbers

None

Natural Product Identification

Common Name

5,14-dihydroxy-2,6,10,14-tetramethylhexadeca-2,6,15-triene-4,12-dione

Description

5,14-Dihydroxy-2,6,10,14-tetramethylhexadeca-2,6,15-triene-4,12-dione belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units. 5,14-dihydroxy-2,6,10,14-tetramethylhexadeca-2,6,15-triene-4,12-dione is found in Croton salutaris. 5,14-Dihydroxy-2,6,10,14-tetramethylhexadeca-2,6,15-triene-4,12-dione is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL SDF PDB SMILES InChI


  Mrv1533004201505262D          

 24 23  0  0  0  0            999 V2000
    1.9520   -1.9520    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9520   -1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2375   -0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5230   -1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1914   -0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1914    0.1105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5230    0.5230    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9059    0.5230    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6204    0.1105    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9059    1.3480    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1914    1.7605    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6204    1.7605    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6204    2.5855    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3349    2.9980    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9059    2.9980    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6664   -0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3809   -1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3809   -1.9520    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0954   -0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8099   -1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3974   -1.8414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2224   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5243   -1.5395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2388   -1.1270    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
  5  4  1  4  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  6  8  1  0  0  0  0
  8  9  1  0  0  0  0
  8 10  1  0  0  0  0
 10 11  2  0  0  0  0
 10 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 13 15  1  0  0  0  0
  2 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 17 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 20 22  1  0  0  0  0
 20 23  1  0  0  0  0
 23 24  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0218327

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(CCC=C(C)C(O)C(=O)C=C(C)C)CC(=O)CC(C)(O)C=C

> <INCHI_IDENTIFIER>
InChI=1S/C20H32O4/c1-7-20(6,24)13-17(21)12-15(4)9-8-10-16(5)19(23)18(22)11-14(2)3/h7,10-11,15,19,23-24H,1,8-9,12-13H2,2-6H3

> <INCHI_KEY>
JOFTXFOZCKYIKJ-UHFFFAOYSA-N

> <FORMULA>
C20H32O4

> <MOLECULAR_WEIGHT>
336.472

> <EXACT_MASS>
336.23005951

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
56

> <JCHEM_AVERAGE_POLARIZABILITY>
38.614236299866114

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
5,14-dihydroxy-2,6,10,14-tetramethylhexadeca-2,6,15-triene-4,12-dione

> <ALOGPS_LOGP>
2.42

> <JCHEM_LOGP>
3.8145591790000006

> <ALOGPS_LOGS>
-4.16

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.532106614059384

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.828474244046063

> <JCHEM_PKA_STRONGEST_BASIC>
-3.0072312861829893

> <JCHEM_POLAR_SURFACE_AREA>
74.6

> <JCHEM_REFRACTIVITY>
99.40549999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
11

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.34e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
5,14-dihydroxy-2,6,10,14-tetramethylhexadeca-2,6,15-triene-4,12-dione

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 20-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   20-APR-15         0                                  
HETATM    1  C   UNK     0       3.644  -3.644   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       3.644  -2.104   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.310  -1.334   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.976  -2.104   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -0.357  -1.334   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -0.357   0.206   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.976   0.976   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -1.691   0.976   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0      -3.025   0.206   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0      -1.691   2.516   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      -0.357   3.286   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0      -3.025   3.286   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -3.025   4.826   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -4.358   5.596   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -1.691   5.596   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       4.977  -1.334   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       6.311  -2.104   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       6.311  -3.644   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       7.645  -1.334   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       8.978  -2.104   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       8.208  -3.437   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       9.748  -0.770   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0      10.312  -2.874   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      11.646  -2.104   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   16                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10   13                                                       
CONECT   13   12   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13                                                            
CONECT   16    2   17                                                       
CONECT   17   16   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17   20                                                       
CONECT   20   19   21   22   23                                             
CONECT   21   20                                                            
CONECT   22   20                                                            
CONECT   23   20   24                                                       
CONECT   24   23                                                            
MASTER        0    0    0    0    0    0    0    0   24    0   46    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₀H₃₂O₄

Average Mass

336.4720 Da

Monoisotopic Mass

336.23006 Da

IUPAC Name

5,14-dihydroxy-2,6,10,14-tetramethylhexadeca-2,6,15-triene-4,12-dione

Traditional Name

5,14-dihydroxy-2,6,10,14-tetramethylhexadeca-2,6,15-triene-4,12-dione

CAS Registry Number

Not Available

SMILES

CC(CCC=C(C)C(O)C(=O)C=C(C)C)CC(=O)CC(C)(O)C=C

InChI Identifier

InChI=1S/C20H32O4/c1-7-20(6,24)13-17(21)12-15(4)9-8-10-16(5)19(23)18(22)11-14(2)3/h7,10-11,15,19,23-24H,1,8-9,12-13H2,2-6H3

InChI Key

JOFTXFOZCKYIKJ-UHFFFAOYSA-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
Croton salutaris	LOTUS Database	35616633

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
Farsesane sesquiterpenoid
Fatty alcohol
Acyloin
Beta-hydroxy ketone
Fatty acyl
Acryloyl-group
Alpha-hydroxy ketone
Enone
Alpha,beta-unsaturated ketone
Tertiary alcohol
Ketone
Secondary alcohol
Hydrocarbon derivative
Alcohol
Carbonyl group
Organic oxide
Organooxygen compound
Organic oxygen compound
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic 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	2.42	ALOGPS
logP	3.81	ChemAxon
logS	-4.2	ALOGPS
pKa (Strongest Acidic)	12.83	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	74.6 Å²	ChemAxon
Rotatable Bond Count	11	ChemAxon
Refractivity	99.41 m³·mol⁻¹	ChemAxon
Polarizability	38.61 Å³	ChemAxon
Number of Rings	0	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

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 5,14-dihydroxy-2,6,10,14-tetramethylhexadeca-2,6,15-triene-4,12-dione (NP0218327)

MOL for NP0218327 (5,14-dihydroxy-2,6,10,14-tetramethylhexadeca-2,6,15-triene-4,12-dione)

3D MOL for NP0218327 (5,14-dihydroxy-2,6,10,14-tetramethylhexadeca-2,6,15-triene-4,12-dione)

3D SDF for NP0218327 (5,14-dihydroxy-2,6,10,14-tetramethylhexadeca-2,6,15-triene-4,12-dione)

3D-SDF for NP0218327 (5,14-dihydroxy-2,6,10,14-tetramethylhexadeca-2,6,15-triene-4,12-dione)

PDB for NP0218327 (5,14-dihydroxy-2,6,10,14-tetramethylhexadeca-2,6,15-triene-4,12-dione)

3D PDB for NP0218327 (5,14-dihydroxy-2,6,10,14-tetramethylhexadeca-2,6,15-triene-4,12-dione)

SMILES for NP0218327 (5,14-dihydroxy-2,6,10,14-tetramethylhexadeca-2,6,15-triene-4,12-dione)

INCHI for NP0218327 (5,14-dihydroxy-2,6,10,14-tetramethylhexadeca-2,6,15-triene-4,12-dione)

Structure for NP0218327 (5,14-dihydroxy-2,6,10,14-tetramethylhexadeca-2,6,15-triene-4,12-dione)

3D Structure for NP0218327 (5,14-dihydroxy-2,6,10,14-tetramethylhexadeca-2,6,15-triene-4,12-dione)