NP-MRD: Showing NP-Card for 9,10-dihydroxy-7,15-dimethyl-20-(octa-2,4-dien-1-yl)-1-azacycloicosa-3,5,7,11,13,15,17-heptaen-2-one (NP0183533)

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Record Information

Version

2.0

Created at

2022-09-03 22:27:39 UTC

Updated at

2022-09-03 22:27:39 UTC

NP-MRD ID

NP0183533

Secondary Accession Numbers

None

Natural Product Identification

Common Name

9,10-dihydroxy-7,15-dimethyl-20-(octa-2,4-dien-1-yl)-1-azacycloicosa-3,5,7,11,13,15,17-heptaen-2-one

Description

Heronamide C belongs to the class of organic compounds known as cyclic carboximidic acids. These are organic acids with the general formula RC(=N)-OH (R=H, organic group), where the carboximidic acid group is part of a cycle. 9,10-dihydroxy-7,15-dimethyl-20-(octa-2,4-dien-1-yl)-1-azacycloicosa-3,5,7,11,13,15,17-heptaen-2-one was first documented in 2016 (PMID: 27331864). Based on a literature review a small amount of articles have been published on Heronamide C (PMID: 34797655) (PMID: 34784214) (PMID: 27171897) (PMID: 27091090).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309042200272D          

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M  END

     RDKit          3D

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M  END


  Mrv1652309042200272D          

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M  END
> <DATABASE_ID>
NP0183533

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCCC=CC=CCC1CC=CC=C(C)C=CC=CC(O)C(O)C=C(C)C=CC=CC(=O)N1

> <INCHI_IDENTIFIER>
InChI=1S/C29H39NO3/c1-4-5-6-7-8-9-19-26-20-13-10-16-24(2)17-11-14-21-27(31)28(32)23-25(3)18-12-15-22-29(33)30-26/h6-18,21-23,26-28,31-32H,4-5,19-20H2,1-3H3,(H,30,33)

> <INCHI_KEY>
QUZNSWBEDCHESP-UHFFFAOYSA-N

> <FORMULA>
C29H39NO3

> <MOLECULAR_WEIGHT>
449.635

> <EXACT_MASS>
449.29299412

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
72

> <JCHEM_AVERAGE_POLARIZABILITY>
53.2514181783208

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
9,10-dihydroxy-7,15-dimethyl-20-(octa-2,4-dien-1-yl)-1-azacycloicosa-3,5,7,11,13,15,17-heptaen-2-one

> <JCHEM_LOGP>
5.134795652

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.876281575549694

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.459838422926474

> <JCHEM_PKA_STRONGEST_BASIC>
-0.11418428915063228

> <JCHEM_POLAR_SURFACE_AREA>
69.56

> <JCHEM_REFRACTIVITY>
149.13480000000007

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
9,10-dihydroxy-7,15-dimethyl-20-(octa-2,4-dien-1-yl)-1-azacycloicosa-3,5,7,11,13,15,17-heptaen-2-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 04-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   04-SEP-22         0                                  
HETATM    1  C   UNK     0      -2.986  10.573   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.464  10.338   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -0.906   8.903   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.616   8.669   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.174   7.233   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.696   6.999   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       3.255   5.564   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.777   5.329   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.335   3.894   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       6.299   5.095   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       7.821   4.861   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       8.379   3.426   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       7.415   2.225   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       7.973   0.789   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       9.495   0.555   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       7.009  -0.412   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       7.567  -1.847   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       6.603  -3.048   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       7.161  -4.483   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       6.197  -5.684   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       6.755  -7.120   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       4.675  -5.450   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       3.711  -6.651   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0       4.117  -4.015   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       2.595  -3.780   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       1.631  -4.981   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       2.037  -2.345   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       3.001  -1.144   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       2.443   0.291   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       3.407   1.492   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       2.849   2.928   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0       1.327   3.162   0.000  0.00  0.00           O+0
HETATM   33  N   UNK     0       3.813   4.129   0.000  0.00  0.00           N+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   33                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   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                                                       
CONECT   20   19   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22   25                                                       
CONECT   25   24   26   27                                                  
CONECT   26   25                                                            
CONECT   27   25   28                                                       
CONECT   28   27   29                                                       
CONECT   29   28   30                                                       
CONECT   30   29   31                                                       
CONECT   31   30   32   33                                                  
CONECT   32   31                                                            
CONECT   33   31    9                                                       
MASTER        0    0    0    0    0    0    0    0   33    0   66    0
END

View in JSmol

Synonyms

Value	Source
8-Deoxyheronamide C	MeSH

Chemical Formula

C₂₉H₃₉NO₃

Average Mass

449.6350 Da

Monoisotopic Mass

449.29299 Da

IUPAC Name

9,10-dihydroxy-7,15-dimethyl-20-(octa-2,4-dien-1-yl)-1-azacycloicosa-3,5,7,11,13,15,17-heptaen-2-one

Traditional Name

9,10-dihydroxy-7,15-dimethyl-20-(octa-2,4-dien-1-yl)-1-azacycloicosa-3,5,7,11,13,15,17-heptaen-2-one

CAS Registry Number

Not Available

SMILES

CCCC=CC=CCC1CC=CC=C(C)C=CC=CC(O)C(O)C=C(C)C=CC=CC(=O)N1

InChI Identifier

InChI=1S/C29H39NO3/c1-4-5-6-7-8-9-19-26-20-13-10-16-24(2)17-11-14-21-27(31)28(32)23-25(3)18-12-15-22-29(33)30-26/h6-18,21-23,26-28,31-32H,4-5,19-20H2,1-3H3,(H,30,33)

InChI Key

QUZNSWBEDCHESP-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

Not Available

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as cyclic carboximidic acids. These are organic acids with the general formula RC(=N)-OH (R=H, organic group), where the carboximidic acid group is part of a cycle.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboximidic acids and derivatives

Sub Class

Carboximidic acids

Direct Parent

Cyclic carboximidic acids

Alternative Parents

Substituents

Cyclic carboximidic acid
1,2-diol
Secondary alcohol
Polyol
Propargyl-type 1,3-dipolar organic compound
Azacycle
Organoheterocyclic compound
Organic 1,3-dipolar compound
Organic nitrogen compound
Hydrocarbon derivative
Organopnictogen compound
Organic oxygen compound
Organooxygen compound
Organonitrogen compound
Alcohol
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	5.13	ChemAxon
pKa (Strongest Acidic)	13.46	ChemAxon
pKa (Strongest Basic)	-0.11	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	69.56 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	149.13 m³·mol⁻¹	ChemAxon
Polarizability	53.25 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	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

75295583

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Fujita K, Sugiyama R, Nishimura S, Ishikawa N, Arai MA, Ishibashi M, Kakeya H: Stereochemical Assignment and Biological Evaluation of BE-14106 Unveils the Importance of One Acetate Unit for the Antifungal Activity of Polyene Macrolactams. J Nat Prod. 2016 Jul 22;79(7):1877-80. doi: 10.1021/acs.jnatprod.6b00250. Epub 2016 Jun 22. [PubMed:27331864 ]
Kanoh N, Terajima Y, Tanaka S, Terashima R, Nishiyama H, Nagasawa S, Sasano Y, Iwabuchi Y, Nishimura S, Kakeya H: Toward the Creation of Induced Pluripotent Small (iPS) Molecules: Establishment of a Modular Synthetic Strategy for the Heronamide C-type Polyene Macrolactams and Their Conformational and Reactivity Analysis. J Org Chem. 2021 Dec 3;86(23):16231-16248. doi: 10.1021/acs.joc.1c01760. Epub 2021 Nov 19. [PubMed:34797655 ]
Kanoh N, Terashima R, Nishiyama H, Terajima Y, Nagasawa S, Sasano Y, Iwabuchi Y, Saito H, Egoshi S, Dodo K, Sodeoka M, Pan C, Ikeuchi Y, Nishimura S, Kakeya H: Design, Synthesis, and Antifungal Activity of 16,17-Dihydroheronamide C and ent-Heronamide C. J Org Chem. 2021 Dec 3;86(23):16249-16258. doi: 10.1021/acs.joc.1c01761. Epub 2021 Nov 16. [PubMed:34784214 ]
Kanoh N, Itoh S, Fujita K, Sakanishi K, Sugiyama R, Terajima Y, Iwabuchi Y, Nishimura S, Kakeya H: Asymmetric Total Synthesis of Heronamides A-C: Stereochemical Confirmation and Impact of Long-Range Stereochemical Communication on the Biological Activity. Chemistry. 2016 Jun 13;22(25):8586-95. doi: 10.1002/chem.201600569. Epub 2016 May 12. [PubMed:27171897 ]
Booth TJ, Alt S, Capon RJ, Wilkinson B: Synchronous intramolecular cycloadditions of the polyene macrolactam polyketide heronamide C. Chem Commun (Camb). 2016 May 11;52(38):6383-6. doi: 10.1039/c6cc01930g. Epub 2016 Apr 19. [PubMed:27091090 ]
LOTUS database [Link]

Showing NP-Card for 9,10-dihydroxy-7,15-dimethyl-20-(octa-2,4-dien-1-yl)-1-azacycloicosa-3,5,7,11,13,15,17-heptaen-2-one (NP0183533)

MOL for NP0183533 (9,10-dihydroxy-7,15-dimethyl-20-(octa-2,4-dien-1-yl)-1-azacycloicosa-3,5,7,11,13,15,17-heptaen-2-one)

3D MOL for NP0183533 (9,10-dihydroxy-7,15-dimethyl-20-(octa-2,4-dien-1-yl)-1-azacycloicosa-3,5,7,11,13,15,17-heptaen-2-one)

3D SDF for NP0183533 (9,10-dihydroxy-7,15-dimethyl-20-(octa-2,4-dien-1-yl)-1-azacycloicosa-3,5,7,11,13,15,17-heptaen-2-one)

3D-SDF for NP0183533 (9,10-dihydroxy-7,15-dimethyl-20-(octa-2,4-dien-1-yl)-1-azacycloicosa-3,5,7,11,13,15,17-heptaen-2-one)

PDB for NP0183533 (9,10-dihydroxy-7,15-dimethyl-20-(octa-2,4-dien-1-yl)-1-azacycloicosa-3,5,7,11,13,15,17-heptaen-2-one)

3D PDB for NP0183533 (9,10-dihydroxy-7,15-dimethyl-20-(octa-2,4-dien-1-yl)-1-azacycloicosa-3,5,7,11,13,15,17-heptaen-2-one)

SMILES for NP0183533 (9,10-dihydroxy-7,15-dimethyl-20-(octa-2,4-dien-1-yl)-1-azacycloicosa-3,5,7,11,13,15,17-heptaen-2-one)

INCHI for NP0183533 (9,10-dihydroxy-7,15-dimethyl-20-(octa-2,4-dien-1-yl)-1-azacycloicosa-3,5,7,11,13,15,17-heptaen-2-one)

Structure for NP0183533 (9,10-dihydroxy-7,15-dimethyl-20-(octa-2,4-dien-1-yl)-1-azacycloicosa-3,5,7,11,13,15,17-heptaen-2-one)

3D Structure for NP0183533 (9,10-dihydroxy-7,15-dimethyl-20-(octa-2,4-dien-1-yl)-1-azacycloicosa-3,5,7,11,13,15,17-heptaen-2-one)