NP-MRD: Showing NP-Card for (2e,10e,12e,16e,18e)-17-ethyl-6-hydroxy-3,5,7,9,11,15-hexamethyl-8-oxo-19-(6-oxo-2,3-dihydropyran-2-yl)nonadeca-2,10,12,16,18-pentaenoic acid (NP0150641)

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Record Information

Version

2.0

Created at

2022-09-02 06:49:02 UTC

Updated at

2022-09-02 06:49:02 UTC

NP-MRD ID

NP0150641

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(2e,10e,12e,16e,18e)-17-ethyl-6-hydroxy-3,5,7,9,11,15-hexamethyl-8-oxo-19-(6-oxo-2,3-dihydropyran-2-yl)nonadeca-2,10,12,16,18-pentaenoic acid

Description

Anguinomycin B belongs to the class of organic compounds known as diterpene lactones. These are diterpenoids containing a lactone moiety. Based on a literature review very few articles have been published on Anguinomycin B.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309022208492D          

 38 38  0  0  0  0            999 V2000
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   -8.5737   -6.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -9.2881   -8.6625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.0026   -9.0750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.0026   -9.9000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.7171  -10.3125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -11.4315   -9.9000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -11.4315   -9.0750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
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 36 38  1  0  0  0  0
M  END

     RDKit          3D

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M  END


  Mrv1652309022208492D          

 38 38  0  0  0  0            999 V2000
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   -1.4289   -6.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -7.8375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -8.6625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -7.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -6.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -7.8375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -7.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -6.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -7.8375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -7.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -6.6000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -7.8375    0.0000 O   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
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 10 12  1  0  0  0  0
  6 12  1  0  0  0  0
  3 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 14 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 19 21  2  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 22 24  1  0  0  0  0
 24 25  2  0  0  0  0
 24 26  1  0  0  0  0
 26 27  1  0  0  0  0
 26 28  1  0  0  0  0
 28 29  1  0  0  0  0
 28 30  1  0  0  0  0
 30 31  1  0  0  0  0
 30 32  1  0  0  0  0
 32 33  1  0  0  0  0
 33 34  1  0  0  0  0
 33 35  2  0  0  0  0
 35 36  1  0  0  0  0
 36 37  2  0  0  0  0
 36 38  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0150641

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC\C(\C=C\C1CC=CC(=O)O1)=C/C(C)C\C=C\C(\C)=C\C(C)C(=O)C(C)C(O)C(C)C\C(C)=C\C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C32H46O6/c1-8-27(15-16-28-13-10-14-30(35)38-28)19-22(3)12-9-11-21(2)17-24(5)31(36)26(7)32(37)25(6)18-23(4)20-29(33)34/h9-11,14-17,19-20,22,24-26,28,32,37H,8,12-13,18H2,1-7H3,(H,33,34)/b11-9+,16-15+,21-17+,23-20+,27-19+

> <INCHI_KEY>
QLEZOSIKJQCEQI-MVGWMUTRSA-N

> <FORMULA>
C32H46O6

> <MOLECULAR_WEIGHT>
526.714

> <EXACT_MASS>
526.329439201

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
84

> <JCHEM_AVERAGE_POLARIZABILITY>
59.97651756954993

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2E,10E,12E,16E,18E)-17-ethyl-6-hydroxy-3,5,7,9,11,15-hexamethyl-8-oxo-19-(6-oxo-3,6-dihydro-2H-pyran-2-yl)nonadeca-2,10,12,16,18-pentaenoic acid

> <ALOGPS_LOGP>
5.58

> <JCHEM_LOGP>
7.210432243333333

> <ALOGPS_LOGS>
-5.49

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
14.457238963433138

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.568903964083474

> <JCHEM_PKA_STRONGEST_BASIC>
-3.006273729904791

> <JCHEM_POLAR_SURFACE_AREA>
100.90000000000002

> <JCHEM_REFRACTIVITY>
158.00640000000007

> <JCHEM_ROTATABLE_BOND_COUNT>
15

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.72e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2E,10E,12E,16E,18E)-17-ethyl-6-hydroxy-3,5,7,9,11,15-hexamethyl-8-oxo-19-(6-oxo-2,3-dihydropyran-2-yl)nonadeca-2,10,12,16,18-pentaenoic 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     -14.670 -11.550   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0     -16.004 -12.320   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0     -16.004 -13.860   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0     -17.338 -14.630   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0     -17.338 -16.170   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0     -18.672 -16.940   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0     -18.672 -18.480   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0     -20.005 -19.250   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0     -21.339 -18.480   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0     -21.339 -16.940   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0     -22.673 -16.170   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0     -20.005 -16.170   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0     -14.670 -14.630   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0     -13.337 -13.860   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0     -13.337 -12.320   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0     -12.003 -14.630   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0     -10.669 -13.860   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -9.336 -14.630   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -8.002 -13.860   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -8.002 -12.320   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -6.668 -14.630   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -5.335 -13.860   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -5.335 -12.320   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      -4.001 -14.630   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0      -4.001 -16.170   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0      -2.667 -13.860   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      -2.667 -12.320   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      -1.334 -14.630   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0      -1.334 -16.170   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0       0.000 -13.860   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       0.000 -12.320   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       1.334 -14.630   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       2.667 -13.860   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       2.667 -12.320   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       4.001 -14.630   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0       5.335 -13.860   0.000  0.00  0.00           C+0
HETATM   37  O   UNK     0       5.335 -12.320   0.000  0.00  0.00           O+0
HETATM   38  O   UNK     0       6.668 -14.630   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   13                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7   12                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10    6                                                       
CONECT   13    3   14                                                       
CONECT   14   13   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19   22                                                       
CONECT   22   21   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22   25   26                                                  
CONECT   25   24                                                            
CONECT   26   24   27   28                                                  
CONECT   27   26                                                            
CONECT   28   26   29   30                                                  
CONECT   29   28                                                            
CONECT   30   28   31   32                                                  
CONECT   31   30                                                            
CONECT   32   30   33                                                       
CONECT   33   32   34   35                                                  
CONECT   34   33                                                            
CONECT   35   33   36                                                       
CONECT   36   35   37   38                                                  
CONECT   37   36                                                            
CONECT   38   36                                                            
MASTER        0    0    0    0    0    0    0    0   38    0   76    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₃₂H₄₆O₆

Average Mass

526.7140 Da

Monoisotopic Mass

526.32944 Da

IUPAC Name

(2E,10E,12E,16E,18E)-17-ethyl-6-hydroxy-3,5,7,9,11,15-hexamethyl-8-oxo-19-(6-oxo-3,6-dihydro-2H-pyran-2-yl)nonadeca-2,10,12,16,18-pentaenoic acid

Traditional Name

(2E,10E,12E,16E,18E)-17-ethyl-6-hydroxy-3,5,7,9,11,15-hexamethyl-8-oxo-19-(6-oxo-2,3-dihydropyran-2-yl)nonadeca-2,10,12,16,18-pentaenoic acid

CAS Registry Number

Not Available

SMILES

CC\C(\C=C\C1CC=CC(=O)O1)=C/C(C)C\C=C\C(\C)=C\C(C)C(=O)C(C)C(O)C(C)C\C(C)=C\C(O)=O

InChI Identifier

InChI=1S/C32H46O6/c1-8-27(15-16-28-13-10-14-30(35)38-28)19-22(3)12-9-11-21(2)17-24(5)31(36)26(7)32(37)25(6)18-23(4)20-29(33)34/h9-11,14-17,19-20,22,24-26,28,32,37H,8,12-13,18H2,1-7H3,(H,33,34)/b11-9+,16-15+,21-17+,23-20+,27-19+

InChI Key

QLEZOSIKJQCEQI-MVGWMUTRSA-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 diterpene lactones. These are diterpenoids containing a lactone moiety.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Terpene lactones

Direct Parent

Diterpene lactones

Alternative Parents

Substituents

Diterpene lactone
Diterpenoid
Long-chain fatty acid
Branched fatty acid
Dihydropyranone
Heterocyclic fatty acid
Methyl-branched fatty acid
Hydroxy fatty acid
Keto fatty acid
Beta-hydroxy ketone
Dicarboxylic acid or derivatives
Fatty acyl
Fatty acid
Unsaturated fatty acid
Pyran
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Secondary alcohol
Carboxylic acid ester
Ketone
Lactone
Organoheterocyclic compound
Oxacycle
Carboxylic acid
Carboxylic acid derivative
Organooxygen compound
Alcohol
Hydrocarbon derivative
Carbonyl group
Organic oxide
Organic oxygen compound
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic 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	5.58	ALOGPS
logP	7.21	ChemAxon
logS	-5.5	ALOGPS
pKa (Strongest Acidic)	4.57	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	100.9 Å²	ChemAxon
Rotatable Bond Count	15	ChemAxon
Refractivity	158.01 m³·mol⁻¹	ChemAxon
Polarizability	59.98 Å³	ChemAxon
Number of Rings	1	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

4948072

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

6444135

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (2e,10e,12e,16e,18e)-17-ethyl-6-hydroxy-3,5,7,9,11,15-hexamethyl-8-oxo-19-(6-oxo-2,3-dihydropyran-2-yl)nonadeca-2,10,12,16,18-pentaenoic acid (NP0150641)

MOL for NP0150641 ((2e,10e,12e,16e,18e)-17-ethyl-6-hydroxy-3,5,7,9,11,15-hexamethyl-8-oxo-19-(6-oxo-2,3-dihydropyran-2-yl)nonadeca-2,10,12,16,18-pentaenoic acid)

3D MOL for NP0150641 ((2e,10e,12e,16e,18e)-17-ethyl-6-hydroxy-3,5,7,9,11,15-hexamethyl-8-oxo-19-(6-oxo-2,3-dihydropyran-2-yl)nonadeca-2,10,12,16,18-pentaenoic acid)

3D SDF for NP0150641 ((2e,10e,12e,16e,18e)-17-ethyl-6-hydroxy-3,5,7,9,11,15-hexamethyl-8-oxo-19-(6-oxo-2,3-dihydropyran-2-yl)nonadeca-2,10,12,16,18-pentaenoic acid)

3D-SDF for NP0150641 ((2e,10e,12e,16e,18e)-17-ethyl-6-hydroxy-3,5,7,9,11,15-hexamethyl-8-oxo-19-(6-oxo-2,3-dihydropyran-2-yl)nonadeca-2,10,12,16,18-pentaenoic acid)

PDB for NP0150641 ((2e,10e,12e,16e,18e)-17-ethyl-6-hydroxy-3,5,7,9,11,15-hexamethyl-8-oxo-19-(6-oxo-2,3-dihydropyran-2-yl)nonadeca-2,10,12,16,18-pentaenoic acid)

3D PDB for NP0150641 ((2e,10e,12e,16e,18e)-17-ethyl-6-hydroxy-3,5,7,9,11,15-hexamethyl-8-oxo-19-(6-oxo-2,3-dihydropyran-2-yl)nonadeca-2,10,12,16,18-pentaenoic acid)

SMILES for NP0150641 ((2e,10e,12e,16e,18e)-17-ethyl-6-hydroxy-3,5,7,9,11,15-hexamethyl-8-oxo-19-(6-oxo-2,3-dihydropyran-2-yl)nonadeca-2,10,12,16,18-pentaenoic acid)

INCHI for NP0150641 ((2e,10e,12e,16e,18e)-17-ethyl-6-hydroxy-3,5,7,9,11,15-hexamethyl-8-oxo-19-(6-oxo-2,3-dihydropyran-2-yl)nonadeca-2,10,12,16,18-pentaenoic acid)

Structure for NP0150641 ((2e,10e,12e,16e,18e)-17-ethyl-6-hydroxy-3,5,7,9,11,15-hexamethyl-8-oxo-19-(6-oxo-2,3-dihydropyran-2-yl)nonadeca-2,10,12,16,18-pentaenoic acid)

3D Structure for NP0150641 ((2e,10e,12e,16e,18e)-17-ethyl-6-hydroxy-3,5,7,9,11,15-hexamethyl-8-oxo-19-(6-oxo-2,3-dihydropyran-2-yl)nonadeca-2,10,12,16,18-pentaenoic acid)