NP-MRD: Showing NP-Card for (2e,10e,12e,16e,18e)-6-hydroxy-3,5,7,9,11,15,17-heptamethyl-8-oxo-19-(6-oxo-2,3-dihydropyran-2-yl)nonadeca-2,10,12,16,18-pentaenoic acid (NP0162801)

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Record Information

Version

2.0

Created at

2022-09-02 21:16:41 UTC

Updated at

2022-09-02 21:16:42 UTC

NP-MRD ID

NP0162801

Secondary Accession Numbers

None

Natural Product Identification

Common Name

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

Description

Anguinomycin A belongs to the class of organic compounds known as diterpene lactones. These are diterpenoids containing a lactone moiety. (2e,10e,12e,16e,18e)-6-hydroxy-3,5,7,9,11,15,17-heptamethyl-8-oxo-19-(6-oxo-2,3-dihydropyran-2-yl)nonadeca-2,10,12,16,18-pentaenoic acid was first documented in 2013 (PMID: 23297231). Based on a literature review very few articles have been published on Anguinomycin A (PMID: 32121612).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309022223162D          

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M  END

     RDKit          3D

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M  END


  Mrv1652309022223162D          

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    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  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
  9 11  1  0  0  0  0
  5 11  1  0  0  0  0
  2 12  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 13 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
 18 19  1  0  0  0  0
 18 20  2  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 21 23  1  0  0  0  0
 23 24  2  0  0  0  0
 23 25  1  0  0  0  0
 25 26  1  0  0  0  0
 25 27  1  0  0  0  0
 27 28  1  0  0  0  0
 27 29  1  0  0  0  0
 29 30  1  0  0  0  0
 29 31  1  0  0  0  0
 31 32  1  0  0  0  0
 32 33  1  0  0  0  0
 32 34  2  0  0  0  0
 34 35  1  0  0  0  0
 35 36  2  0  0  0  0
 35 37  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0162801

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C31H44O6/c1-20(16-22(3)14-15-27-12-9-13-29(34)37-27)10-8-11-21(2)17-24(5)30(35)26(7)31(36)25(6)18-23(4)19-28(32)33/h8-9,11,13-17,19-20,24-27,31,36H,10,12,18H2,1-7H3,(H,32,33)/b11-8+,15-14+,21-17+,22-16+,23-19+

> <INCHI_KEY>
SGYKTDIJCLHSET-QMTWAXRBSA-N

> <FORMULA>
C31H44O6

> <MOLECULAR_WEIGHT>
512.687

> <EXACT_MASS>
512.313789137

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
81

> <JCHEM_AVERAGE_POLARIZABILITY>
58.446366935656656

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

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

> <ALOGPS_LOGP>
5.24

> <JCHEM_LOGP>
6.765863578333334

> <ALOGPS_LOGS>
-5.40

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
14.457242578777706

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.568903964083475

> <JCHEM_PKA_STRONGEST_BASIC>
-3.006273729904791

> <JCHEM_POLAR_SURFACE_AREA>
100.90000000000002

> <JCHEM_REFRACTIVITY>
153.40540000000004

> <JCHEM_ROTATABLE_BOND_COUNT>
14

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.04e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2E,10E,12E,16E,18E)-6-hydroxy-3,5,7,9,11,15,17-heptamethyl-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     -16.004 -12.320   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0     -16.004 -13.860   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0     -17.338 -14.630   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0     -17.338 -16.170   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0     -18.672 -16.940   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0     -18.672 -18.480   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0     -20.005 -19.250   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0     -21.339 -18.480   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0     -21.339 -16.940   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0     -22.673 -16.170   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0     -20.005 -16.170   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0     -14.670 -14.630   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0     -13.337 -13.860   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0     -13.337 -12.320   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0     -12.003 -14.630   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0     -10.669 -13.860   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -9.336 -14.630   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -8.002 -13.860   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -8.002 -12.320   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -6.668 -14.630   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -5.335 -13.860   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -5.335 -12.320   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -4.001 -14.630   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0      -4.001 -16.170   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0      -2.667 -13.860   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      -2.667 -12.320   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      -1.334 -14.630   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0      -1.334 -16.170   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0       0.000 -13.860   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       0.000 -12.320   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       1.334 -14.630   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       2.667 -13.860   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       2.667 -12.320   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       4.001 -14.630   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       5.335 -13.860   0.000  0.00  0.00           C+0
HETATM   36  O   UNK     0       5.335 -12.320   0.000  0.00  0.00           O+0
HETATM   37  O   UNK     0       6.668 -14.630   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   12                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6   11                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9    5                                                       
CONECT   12    2   13                                                       
CONECT   13   12   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18   21                                                       
CONECT   21   20   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23   26   27                                                  
CONECT   26   25                                                            
CONECT   27   25   28   29                                                  
CONECT   28   27                                                            
CONECT   29   27   30   31                                                  
CONECT   30   29                                                            
CONECT   31   29   32                                                       
CONECT   32   31   33   34                                                  
CONECT   33   32                                                            
CONECT   34   32   35                                                       
CONECT   35   34   36   37                                                  
CONECT   36   35                                                            
CONECT   37   35                                                            
MASTER        0    0    0    0    0    0    0    0   37    0   74    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₃₁H₄₄O₆

Average Mass

512.6870 Da

Monoisotopic Mass

512.31379 Da

IUPAC Name

(2E,10E,12E,16E,18E)-6-hydroxy-3,5,7,9,11,15,17-heptamethyl-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)-6-hydroxy-3,5,7,9,11,15,17-heptamethyl-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\C(\C)=C\C(C)C(=O)C(C)C(O)C(C)C\C(C)=C\C(O)=O)\C=C(/C)\C=C\C1CC=CC(=O)O1

InChI Identifier

InChI=1S/C31H44O6/c1-20(16-22(3)14-15-27-12-9-13-29(34)37-27)10-8-11-21(2)17-24(5)30(35)26(7)31(36)25(6)18-23(4)19-28(32)33/h8-9,11,13-17,19-20,24-27,31,36H,10,12,18H2,1-7H3,(H,32,33)/b11-8+,15-14+,21-17+,22-16+,23-19+

InChI Key

SGYKTDIJCLHSET-QMTWAXRBSA-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	5.24	ALOGPS
logP	6.77	ChemAxon
logS	-5.4	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	14	ChemAxon
Refractivity	153.41 m³·mol⁻¹	ChemAxon
Polarizability	58.45 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

4948073

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

6444136

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Sun Q, Carrasco YP, Hu Y, Guo X, Mirzaei H, Macmillan J, Chook YM: Nuclear export inhibition through covalent conjugation and hydrolysis of Leptomycin B by CRM1. Proc Natl Acad Sci U S A. 2013 Jan 22;110(4):1303-8. doi: 10.1073/pnas.1217203110. Epub 2013 Jan 7. [PubMed:23297231 ]
Sujarit K, Mori M, Dobashi K, Shiomi K, Pathom-Aree W, Lumyong S: New Antimicrobial Phenyl Alkenoic Acids Isolated from an Oil Palm Rhizosphere-Associated Actinomycete, Streptomyces palmae CMU-AB204(T). Microorganisms. 2020 Mar 1;8(3):350. doi: 10.3390/microorganisms8030350. [PubMed:32121612 ]
LOTUS database [Link]

Showing NP-Card for (2e,10e,12e,16e,18e)-6-hydroxy-3,5,7,9,11,15,17-heptamethyl-8-oxo-19-(6-oxo-2,3-dihydropyran-2-yl)nonadeca-2,10,12,16,18-pentaenoic acid (NP0162801)

MOL for NP0162801 ((2e,10e,12e,16e,18e)-6-hydroxy-3,5,7,9,11,15,17-heptamethyl-8-oxo-19-(6-oxo-2,3-dihydropyran-2-yl)nonadeca-2,10,12,16,18-pentaenoic acid)

3D MOL for NP0162801 ((2e,10e,12e,16e,18e)-6-hydroxy-3,5,7,9,11,15,17-heptamethyl-8-oxo-19-(6-oxo-2,3-dihydropyran-2-yl)nonadeca-2,10,12,16,18-pentaenoic acid)

3D SDF for NP0162801 ((2e,10e,12e,16e,18e)-6-hydroxy-3,5,7,9,11,15,17-heptamethyl-8-oxo-19-(6-oxo-2,3-dihydropyran-2-yl)nonadeca-2,10,12,16,18-pentaenoic acid)

3D-SDF for NP0162801 ((2e,10e,12e,16e,18e)-6-hydroxy-3,5,7,9,11,15,17-heptamethyl-8-oxo-19-(6-oxo-2,3-dihydropyran-2-yl)nonadeca-2,10,12,16,18-pentaenoic acid)

PDB for NP0162801 ((2e,10e,12e,16e,18e)-6-hydroxy-3,5,7,9,11,15,17-heptamethyl-8-oxo-19-(6-oxo-2,3-dihydropyran-2-yl)nonadeca-2,10,12,16,18-pentaenoic acid)

3D PDB for NP0162801 ((2e,10e,12e,16e,18e)-6-hydroxy-3,5,7,9,11,15,17-heptamethyl-8-oxo-19-(6-oxo-2,3-dihydropyran-2-yl)nonadeca-2,10,12,16,18-pentaenoic acid)

SMILES for NP0162801 ((2e,10e,12e,16e,18e)-6-hydroxy-3,5,7,9,11,15,17-heptamethyl-8-oxo-19-(6-oxo-2,3-dihydropyran-2-yl)nonadeca-2,10,12,16,18-pentaenoic acid)

INCHI for NP0162801 ((2e,10e,12e,16e,18e)-6-hydroxy-3,5,7,9,11,15,17-heptamethyl-8-oxo-19-(6-oxo-2,3-dihydropyran-2-yl)nonadeca-2,10,12,16,18-pentaenoic acid)

Structure for NP0162801 ((2e,10e,12e,16e,18e)-6-hydroxy-3,5,7,9,11,15,17-heptamethyl-8-oxo-19-(6-oxo-2,3-dihydropyran-2-yl)nonadeca-2,10,12,16,18-pentaenoic acid)

3D Structure for NP0162801 ((2e,10e,12e,16e,18e)-6-hydroxy-3,5,7,9,11,15,17-heptamethyl-8-oxo-19-(6-oxo-2,3-dihydropyran-2-yl)nonadeca-2,10,12,16,18-pentaenoic acid)