NP-MRD: Showing NP-Card for (3e,5e,7e,13z,15e,17e,19e)-22-[(2e)-hex-2-en-1-yl]-17-methyl-1-azacyclodocosa-1,3,5,7,13,15,17,19-octaene-2,9,10,12-tetrol (NP0195427)

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Record Information

Version

2.0

Created at

2022-09-04 13:17:13 UTC

Updated at

2022-09-04 13:17:13 UTC

NP-MRD ID

NP0195427

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(3e,5e,7e,13z,15e,17e,19e)-22-[(2e)-hex-2-en-1-yl]-17-methyl-1-azacyclodocosa-1,3,5,7,13,15,17,19-octaene-2,9,10,12-tetrol

Description

Aureoverticillactam belongs to the class of organic compounds known as macrolactams. These are cyclic amides of amino carboxylic acids, having a 1-azacycloalkan-2-one structure, or analogues having unsaturation or heteroatoms replacing one or more carbon atoms of the ring. They are nitrogen analogues (the a nitrogen atom replacing the o atom of the cyclic carboxylic acid group ) of the naturally occurring macrolides. (3e,5e,7e,13z,15e,17e,19e)-22-[(2e)-hex-2-en-1-yl]-17-methyl-1-azacyclodocosa-1,3,5,7,13,15,17,19-octaene-2,9,10,12-tetrol is found in Streptomyces aureoverticillatus. (3e,5e,7e,13z,15e,17e,19e)-22-[(2e)-hex-2-en-1-yl]-17-methyl-1-azacyclodocosa-1,3,5,7,13,15,17,19-octaene-2,9,10,12-tetrol was first documented in 2004 (PMID: 15332863). Based on a literature review very few articles have been published on Aureoverticillactam (PMID: 33900117).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309042215172D          

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M  END

     RDKit          3D

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M  END


  Mrv1652309042215172D          

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M  END
> <DATABASE_ID>
NP0195427

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCC\C=C\CC1C\C=C\C=C(/C)\C=C\C=C/C(O)CC(O)C(O)\C=C\C=C\C=C\C(O)=N1

> <INCHI_IDENTIFIER>
InChI=1S/C28H39NO4/c1-3-4-5-8-17-24-18-13-11-15-23(2)16-12-14-19-25(30)22-27(32)26(31)20-9-6-7-10-21-28(33)29-24/h5-16,19-21,24-27,30-32H,3-4,17-18,22H2,1-2H3,(H,29,33)/b7-6+,8-5+,13-11+,16-12+,19-14-,20-9+,21-10+,23-15+

> <INCHI_KEY>
VMKRIAILWBEBLR-TWCCLTHVSA-N

> <FORMULA>
C28H39NO4

> <MOLECULAR_WEIGHT>
453.623

> <EXACT_MASS>
453.28790874

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
72

> <JCHEM_AVERAGE_POLARIZABILITY>
53.22664759573119

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(3E,5E,7E,13Z,15E,17E,19E)-22-[(2E)-hex-2-en-1-yl]-17-methyl-1-azacyclodocosa-1,3,5,7,13,15,17,19-octaene-2,9,10,12-tetrol

> <JCHEM_LOGP>
4.2954645896528

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.594377163444442

> <JCHEM_PKA_STRONGEST_ACIDIC>
6.803658012764136

> <JCHEM_PKA_STRONGEST_BASIC>
4.854273727886573

> <JCHEM_POLAR_SURFACE_AREA>
93.28000000000002

> <JCHEM_REFRACTIVITY>
145.88380000000004

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(3E,5E,7E,13Z,15E,17E,19E)-22-[(2E)-hex-2-en-1-yl]-17-methyl-1-azacyclodocosa-1,3,5,7,13,15,17,19-octaene-2,9,10,12-tetrol

> <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      -1.170   9.178   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.366   9.277   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.220   7.995   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.757   8.094   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       3.611   6.812   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       5.148   6.911   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.002   5.629   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       7.538   5.727   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       8.392   4.446   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       7.709   3.066   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       8.563   1.784   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       7.880   0.404   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       6.343   0.305   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       8.734  -0.878   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       8.051  -2.258   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       8.904  -3.540   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       8.221  -4.920   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       6.685  -5.019   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       7.538  -6.300   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       6.002  -6.399   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       4.465  -6.497   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       3.782  -7.878   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       3.611  -5.216   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       2.074  -5.314   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       4.294  -3.836   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       3.440  -2.554   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       4.123  -1.174   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       3.269   0.108   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       3.952   1.488   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       3.099   2.770   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       3.782   4.150   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0       2.928   5.432   0.000  0.00  0.00           O+0
HETATM   33  N   UNK     0       5.319   4.249   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   33                                                  
CONECT    8    7    9                                                       
CONECT    9    8   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                                                       
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                                                       
CONECT   26   25   27                                                       
CONECT   27   26   28                                                       
CONECT   28   27   29                                                       
CONECT   29   28   30                                                       
CONECT   30   29   31                                                       
CONECT   31   30   32   33                                                  
CONECT   32   31                                                            
CONECT   33   31    7                                                       
MASTER        0    0    0    0    0    0    0    0   33    0   66    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₈H₃₉NO₄

Average Mass

453.6230 Da

Monoisotopic Mass

453.28791 Da

IUPAC Name

(3E,5E,7E,13Z,15E,17E,19E)-22-[(2E)-hex-2-en-1-yl]-17-methyl-1-azacyclodocosa-1,3,5,7,13,15,17,19-octaene-2,9,10,12-tetrol

Traditional Name

(3E,5E,7E,13Z,15E,17E,19E)-22-[(2E)-hex-2-en-1-yl]-17-methyl-1-azacyclodocosa-1,3,5,7,13,15,17,19-octaene-2,9,10,12-tetrol

CAS Registry Number

Not Available

SMILES

CCC\C=C\CC1C\C=C\C=C(/C)\C=C\C=C/C(O)CC(O)C(O)\C=C\C=C\C=C\C(O)=N1

InChI Identifier

InChI=1S/C28H39NO4/c1-3-4-5-8-17-24-18-13-11-15-23(2)16-12-14-19-25(30)22-27(32)26(31)20-9-6-7-10-21-28(33)29-24/h5-16,19-21,24-27,30-32H,3-4,17-18,22H2,1-2H3,(H,29,33)/b7-6+,8-5+,13-11+,16-12+,19-14-,20-9+,21-10+,23-15+

InChI Key

VMKRIAILWBEBLR-TWCCLTHVSA-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
Streptomyces aureoverticillatus	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as macrolactams. These are cyclic amides of amino carboxylic acids, having a 1-azacycloalkan-2-one structure, or analogues having unsaturation or heteroatoms replacing one or more carbon atoms of the ring. They are nitrogen analogues (the a nitrogen atom replacing the o atom of the cyclic carboxylic acid group ) of the naturally occurring macrolides.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Macrolactams

Sub Class

Not Available

Direct Parent

Macrolactams

Alternative Parents

Substituents

Macrolactam
Carboxamide group
Lactam
Secondary alcohol
Secondary carboxylic acid amide
Carboxylic acid derivative
Polyol
Azacycle
Organoheterocyclic compound
Organooxygen compound
Organonitrogen compound
Organic oxide
Organic oxygen compound
Alcohol
Hydrocarbon derivative
Carbonyl group
Organic nitrogen 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	4.3	ChemAxon
pKa (Strongest Acidic)	6.8	ChemAxon
pKa (Strongest Basic)	4.85	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	93.28 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	145.88 m³·mol⁻¹	ChemAxon
Polarizability	53.23 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	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

C00043304

Chemspider ID

8044227

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Aureoverticillactam

METLIN ID

Not Available

PubChem Compound

9868536

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Mitchell SS, Nicholson B, Teisan S, Lam KS, Potts BC: Aureoverticillactam, a novel 22-atom macrocyclic lactam from the marine actinomycete Streptomyces aureoverticillatus. J Nat Prod. 2004 Aug;67(8):1400-2. doi: 10.1021/np049970g. [PubMed:15332863 ]
Wang LY, Zhang YF, Yang DY, Zhang SJ, Han DD, Luo YP: Aureoverticillactam, a Potent Antifungal Macrocyclic Lactam from Streptomyces aureoverticillatus HN6, Generates Calcium Dyshomeostasis-Induced Cell Apoptosis via the Phospholipase C Pathway in Fusarium oxysporum f. sp. cubense Race 4. Phytopathology. 2021 Nov;111(11):2010-2022. doi: 10.1094/PHYTO-12-20-0543-R. Epub 2021 Nov 22. [PubMed:33900117 ]
LOTUS database [Link]

Showing NP-Card for (3e,5e,7e,13z,15e,17e,19e)-22-[(2e)-hex-2-en-1-yl]-17-methyl-1-azacyclodocosa-1,3,5,7,13,15,17,19-octaene-2,9,10,12-tetrol (NP0195427)

MOL for NP0195427 ((3e,5e,7e,13z,15e,17e,19e)-22-[(2e)-hex-2-en-1-yl]-17-methyl-1-azacyclodocosa-1,3,5,7,13,15,17,19-octaene-2,9,10,12-tetrol)

3D MOL for NP0195427 ((3e,5e,7e,13z,15e,17e,19e)-22-[(2e)-hex-2-en-1-yl]-17-methyl-1-azacyclodocosa-1,3,5,7,13,15,17,19-octaene-2,9,10,12-tetrol)

3D SDF for NP0195427 ((3e,5e,7e,13z,15e,17e,19e)-22-[(2e)-hex-2-en-1-yl]-17-methyl-1-azacyclodocosa-1,3,5,7,13,15,17,19-octaene-2,9,10,12-tetrol)

3D-SDF for NP0195427 ((3e,5e,7e,13z,15e,17e,19e)-22-[(2e)-hex-2-en-1-yl]-17-methyl-1-azacyclodocosa-1,3,5,7,13,15,17,19-octaene-2,9,10,12-tetrol)

PDB for NP0195427 ((3e,5e,7e,13z,15e,17e,19e)-22-[(2e)-hex-2-en-1-yl]-17-methyl-1-azacyclodocosa-1,3,5,7,13,15,17,19-octaene-2,9,10,12-tetrol)

3D PDB for NP0195427 ((3e,5e,7e,13z,15e,17e,19e)-22-[(2e)-hex-2-en-1-yl]-17-methyl-1-azacyclodocosa-1,3,5,7,13,15,17,19-octaene-2,9,10,12-tetrol)

SMILES for NP0195427 ((3e,5e,7e,13z,15e,17e,19e)-22-[(2e)-hex-2-en-1-yl]-17-methyl-1-azacyclodocosa-1,3,5,7,13,15,17,19-octaene-2,9,10,12-tetrol)

INCHI for NP0195427 ((3e,5e,7e,13z,15e,17e,19e)-22-[(2e)-hex-2-en-1-yl]-17-methyl-1-azacyclodocosa-1,3,5,7,13,15,17,19-octaene-2,9,10,12-tetrol)

Structure for NP0195427 ((3e,5e,7e,13z,15e,17e,19e)-22-[(2e)-hex-2-en-1-yl]-17-methyl-1-azacyclodocosa-1,3,5,7,13,15,17,19-octaene-2,9,10,12-tetrol)

3D Structure for NP0195427 ((3e,5e,7e,13z,15e,17e,19e)-22-[(2e)-hex-2-en-1-yl]-17-methyl-1-azacyclodocosa-1,3,5,7,13,15,17,19-octaene-2,9,10,12-tetrol)