NP-MRD: Showing NP-Card for (2z,5r,7e,11e)-2-[(4z)-6-hydroxy-4-(hydroxymethyl)hex-4-en-1-ylidene]-8,12,16-trimethyl-5-(prop-1-en-2-yl)heptadeca-7,11,15-trienoic acid (NP0151696)

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Record Information

Version

2.0

Created at

2022-09-02 08:02:51 UTC

Updated at

2022-09-02 08:02:51 UTC

NP-MRD ID

NP0151696

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(2z,5r,7e,11e)-2-[(4z)-6-hydroxy-4-(hydroxymethyl)hex-4-en-1-ylidene]-8,12,16-trimethyl-5-(prop-1-en-2-yl)heptadeca-7,11,15-trienoic acid

Description

(2Z,5R,7E,11E)-2-[(4Z)-6-hydroxy-4-(hydroxymethyl)hex-4-en-1-ylidene]-8,12,16-trimethyl-5-(prop-1-en-2-yl)heptadeca-7,11,15-trienoic acid belongs to the class of organic compounds known as acyclic diterpenoids. These are diterpenoids (compounds made of four consecutive isoprene units) that do not contain a cycle. Based on a literature review very few articles have been published on (2Z,5R,7E,11E)-2-[(4Z)-6-hydroxy-4-(hydroxymethyl)hex-4-en-1-ylidene]-8,12,16-trimethyl-5-(prop-1-en-2-yl)heptadeca-7,11,15-trienoic acid.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309022210022D          

 34 33  0  0  1  0            999 V2000
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 32 34  1  0  0  0  0
M  END

     RDKit          3D

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M  END


  Mrv1652309022210022D          

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  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  4  2  1  1  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  7  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 12 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 17 19  1  0  0  0  0
  4 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  2  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 26 30  1  0  0  0  0
 30 31  1  0  0  0  0
 22 32  1  0  0  0  0
 32 33  2  0  0  0  0
 32 34  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0151696

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)=CCC\C(C)=C\CC\C(C)=C\C[C@@H](CC\C(=C\CC\C(CO)=C\CO)C(O)=O)C(C)=C

> <INCHI_IDENTIFIER>
InChI=1S/C30H48O4/c1-23(2)10-7-11-25(5)12-8-13-26(6)16-17-28(24(3)4)18-19-29(30(33)34)15-9-14-27(22-32)20-21-31/h10,12,15-16,20,28,31-32H,3,7-9,11,13-14,17-19,21-22H2,1-2,4-6H3,(H,33,34)/b25-12+,26-16+,27-20-,29-15-/t28-/m0/s1

> <INCHI_KEY>
WSHGHMBSDULCKQ-QJMPHGBISA-N

> <FORMULA>
C30H48O4

> <MOLECULAR_WEIGHT>
472.71

> <EXACT_MASS>
472.355260026

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
82

> <JCHEM_AVERAGE_POLARIZABILITY>
59.01182617037115

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2Z,5R,7E,11E)-2-[(4Z)-6-hydroxy-4-(hydroxymethyl)hex-4-en-1-ylidene]-8,12,16-trimethyl-5-(prop-1-en-2-yl)heptadeca-7,11,15-trienoic acid

> <ALOGPS_LOGP>
6.08

> <JCHEM_LOGP>
6.95254594

> <ALOGPS_LOGS>
-5.22

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
15.02215641291098

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.926762128656671

> <JCHEM_PKA_STRONGEST_BASIC>
-2.5275911336194268

> <JCHEM_POLAR_SURFACE_AREA>
77.76

> <JCHEM_REFRACTIVITY>
148.75950000000006

> <JCHEM_ROTATABLE_BOND_COUNT>
18

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.88e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2Z,5R,7E,11E)-2-[(4Z)-6-hydroxy-4-(hydroxymethyl)hex-4-en-1-ylidene]-8,12,16-trimethyl-5-(prop-1-en-2-yl)heptadeca-7,11,15-trienoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 02-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   02-SEP-22         0                                  
HETATM    1  C   UNK     0       3.644  -0.976   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.310  -0.206   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.976  -0.976   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.310   1.334   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.976   2.104   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -0.357   1.334   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -1.691   2.104   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -1.691   3.644   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -3.025   1.334   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -4.358   2.104   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -5.692   1.334   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -7.026   2.104   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -7.026   3.644   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -8.359   1.334   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -9.693   2.104   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0     -11.027   1.334   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0     -12.360   2.104   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0     -13.694   1.334   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0     -12.360   3.644   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       3.644   2.104   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       4.977   1.334   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       6.311   2.104   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       7.645   1.334   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       8.978   2.104   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      10.312   1.334   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      11.646   2.104   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      12.979   1.334   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      14.313   2.104   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0      14.313   3.644   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0      11.646   3.644   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0      12.979   4.414   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0       6.311   3.644   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0       7.645   4.414   0.000  0.00  0.00           O+0
HETATM   34  O   UNK     0       4.977   4.414   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5   20                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17                                                            
CONECT   20    4   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   23   32                                                  
CONECT   23   22   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24   26                                                       
CONECT   26   25   27   30                                                  
CONECT   27   26   28                                                       
CONECT   28   27   29                                                       
CONECT   29   28                                                            
CONECT   30   26   31                                                       
CONECT   31   30                                                            
CONECT   32   22   33   34                                                  
CONECT   33   32                                                            
CONECT   34   32                                                            
MASTER        0    0    0    0    0    0    0    0   34    0   66    0
END

View in JSmol

Synonyms

Value	Source
(2Z,5R,7E,11E)-2-[(4Z)-6-Hydroxy-4-(hydroxymethyl)hex-4-en-1-ylidene]-8,12,16-trimethyl-5-(prop-1-en-2-yl)heptadeca-7,11,15-trienoate	Generator

Chemical Formula

C₃₀H₄₈O₄

Average Mass

472.7100 Da

Monoisotopic Mass

472.35526 Da

IUPAC Name

(2Z,5R,7E,11E)-2-[(4Z)-6-hydroxy-4-(hydroxymethyl)hex-4-en-1-ylidene]-8,12,16-trimethyl-5-(prop-1-en-2-yl)heptadeca-7,11,15-trienoic acid

Traditional Name

(2Z,5R,7E,11E)-2-[(4Z)-6-hydroxy-4-(hydroxymethyl)hex-4-en-1-ylidene]-8,12,16-trimethyl-5-(prop-1-en-2-yl)heptadeca-7,11,15-trienoic acid

CAS Registry Number

Not Available

SMILES

CC(C)=CCC\C(C)=C\CC\C(C)=C\C[C@@H](CC\C(=C\CC\C(CO)=C\CO)C(O)=O)C(C)=C

InChI Identifier

InChI=1S/C30H48O4/c1-23(2)10-7-11-25(5)12-8-13-26(6)16-17-28(24(3)4)18-19-29(30(33)34)15-9-14-27(22-32)20-21-31/h10,12,15-16,20,28,31-32H,3,7-9,11,13-14,17-19,21-22H2,1-2,4-6H3,(H,33,34)/b25-12+,26-16+,27-20-,29-15-/t28-/m0/s1

InChI Key

WSHGHMBSDULCKQ-QJMPHGBISA-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

Not Available

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as acyclic diterpenoids. These are diterpenoids (compounds made of four consecutive isoprene units) that do not contain a cycle.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Diterpenoids

Direct Parent

Acyclic diterpenoids

Alternative Parents

Substituents

Acyclic diterpenoid
Long-chain fatty acid
Branched fatty acid
Hydroxy fatty acid
Methyl-branched fatty acid
Fatty acyl
Fatty acid
Unsaturated fatty acid
Carboxylic acid derivative
Carboxylic acid
Monocarboxylic acid or derivatives
Hydrocarbon derivative
Alcohol
Organic oxygen compound
Carbonyl group
Organic oxide
Primary alcohol
Organooxygen 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	6.08	ALOGPS
logP	6.95	ChemAxon
logS	-5.2	ALOGPS
pKa (Strongest Acidic)	4.93	ChemAxon
pKa (Strongest Basic)	-2.5	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	77.76 Å²	ChemAxon
Rotatable Bond Count	18	ChemAxon
Refractivity	148.76 m³·mol⁻¹	ChemAxon
Polarizability	59.01 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	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

163195489

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (2z,5r,7e,11e)-2-[(4z)-6-hydroxy-4-(hydroxymethyl)hex-4-en-1-ylidene]-8,12,16-trimethyl-5-(prop-1-en-2-yl)heptadeca-7,11,15-trienoic acid (NP0151696)

MOL for NP0151696 ((2z,5r,7e,11e)-2-[(4z)-6-hydroxy-4-(hydroxymethyl)hex-4-en-1-ylidene]-8,12,16-trimethyl-5-(prop-1-en-2-yl)heptadeca-7,11,15-trienoic acid)

3D MOL for NP0151696 ((2z,5r,7e,11e)-2-[(4z)-6-hydroxy-4-(hydroxymethyl)hex-4-en-1-ylidene]-8,12,16-trimethyl-5-(prop-1-en-2-yl)heptadeca-7,11,15-trienoic acid)

3D SDF for NP0151696 ((2z,5r,7e,11e)-2-[(4z)-6-hydroxy-4-(hydroxymethyl)hex-4-en-1-ylidene]-8,12,16-trimethyl-5-(prop-1-en-2-yl)heptadeca-7,11,15-trienoic acid)

3D-SDF for NP0151696 ((2z,5r,7e,11e)-2-[(4z)-6-hydroxy-4-(hydroxymethyl)hex-4-en-1-ylidene]-8,12,16-trimethyl-5-(prop-1-en-2-yl)heptadeca-7,11,15-trienoic acid)

PDB for NP0151696 ((2z,5r,7e,11e)-2-[(4z)-6-hydroxy-4-(hydroxymethyl)hex-4-en-1-ylidene]-8,12,16-trimethyl-5-(prop-1-en-2-yl)heptadeca-7,11,15-trienoic acid)

3D PDB for NP0151696 ((2z,5r,7e,11e)-2-[(4z)-6-hydroxy-4-(hydroxymethyl)hex-4-en-1-ylidene]-8,12,16-trimethyl-5-(prop-1-en-2-yl)heptadeca-7,11,15-trienoic acid)

SMILES for NP0151696 ((2z,5r,7e,11e)-2-[(4z)-6-hydroxy-4-(hydroxymethyl)hex-4-en-1-ylidene]-8,12,16-trimethyl-5-(prop-1-en-2-yl)heptadeca-7,11,15-trienoic acid)

INCHI for NP0151696 ((2z,5r,7e,11e)-2-[(4z)-6-hydroxy-4-(hydroxymethyl)hex-4-en-1-ylidene]-8,12,16-trimethyl-5-(prop-1-en-2-yl)heptadeca-7,11,15-trienoic acid)

Structure for NP0151696 ((2z,5r,7e,11e)-2-[(4z)-6-hydroxy-4-(hydroxymethyl)hex-4-en-1-ylidene]-8,12,16-trimethyl-5-(prop-1-en-2-yl)heptadeca-7,11,15-trienoic acid)

3D Structure for NP0151696 ((2z,5r,7e,11e)-2-[(4z)-6-hydroxy-4-(hydroxymethyl)hex-4-en-1-ylidene]-8,12,16-trimethyl-5-(prop-1-en-2-yl)heptadeca-7,11,15-trienoic acid)