NP-MRD: Showing NP-Card for Marcfortine A (NP0066247)

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Record Information

Version

2.0

Created at

2022-04-28 10:25:58 UTC

Updated at

2022-04-28 10:25:58 UTC

NP-MRD ID

NP0066247

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Marcfortine A

Description

Marcfortine A belongs to the class of organic compounds known as piperazinopiperidines. These are organic aromatic compounds containing a piperazine ring fused to a piperidine. Marcfortine A is found in Aspergillus carneus and Penicillium roqueforti. Marcfortine A was first documented in 2003 (PMID: 12945765). Based on a literature review a small amount of articles have been published on Marcfortine A (PMID: 35347677) (PMID: 27707355) (PMID: 20213172) (PMID: 17117820).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304282212252D          

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M  END

     RDKit          3D

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M  END


  Mrv1652304282212252D          

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M  END
> <DATABASE_ID>
NP0066247

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CN1C(=O)[C@@]23CCCCN2C[C@@]11C[C@@]2(C(=O)NC4=C5OC=CC(C)(C)OC5=CC=C24)C(C)(C)[C@@H]1C3

> <INCHI_IDENTIFIER>
InChI=1S/C28H35N3O4/c1-24(2)11-13-34-21-18(35-24)9-8-17-20(21)29-22(32)28(17)15-27-16-31-12-7-6-10-26(31,23(33)30(27)5)14-19(27)25(28,3)4/h8-9,11,13,19H,6-7,10,12,14-16H2,1-5H3,(H,29,32)/t19-,26-,27+,28+/m0/s1

> <INCHI_KEY>
KYKUTNUWXQVSSU-ZALBMCOMSA-N

> <FORMULA>
C28H35N3O4

> <MOLECULAR_WEIGHT>
477.605

> <EXACT_MASS>
477.262756619

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
70

> <JCHEM_AVERAGE_POLARIZABILITY>
52.48681457119778

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1'S,8R,8'S,10'S)-4,4,11',11',14'-pentamethyl-9,10-dihydro-4H-3',14'-diazaspiro[[1,4]dioxepino[2,3-g]indole-8,12'-tetracyclo[6.5.2.0^{1,10}.0^{3,8}]pentadecane]-9,15'-dione

> <ALOGPS_LOGP>
4.05

> <JCHEM_LOGP>
2.9168377769999974

> <ALOGPS_LOGS>
-3.66

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
7

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.591617733711635

> <JCHEM_PKA_STRONGEST_BASIC>
6.1491142823267095

> <JCHEM_POLAR_SURFACE_AREA>
71.11000000000001

> <JCHEM_REFRACTIVITY>
133.55549999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.05e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1'S,8R,8'S,10'S)-4,4,11',11',14'-pentamethyl-10H-3',14'-diazaspiro[[1,4]dioxepino[2,3-g]indole-8,12'-tetracyclo[6.5.2.0^{1,10}.0^{3,8}]pentadecane]-9,15'-dione

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 28-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   28-APR-22         0                                  
HETATM    1  C   UNK     0      14.893  -0.286   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      16.189   0.546   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      16.117   2.084   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      14.749   2.791   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      13.453   1.960   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      13.525   0.421   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      12.262   2.936   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      12.822   4.370   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0      11.991   5.667   0.000  0.00  0.00           O+0
HETATM   10  N   UNK     0      14.359   4.281   0.000  0.00  0.00           N+0
HETATM   11  C   UNK     0      11.537   1.540   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       9.949   1.429   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       9.523   3.095   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      10.960   3.801   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       7.931   3.756   0.000  0.00  0.00           C+0
HETATM   16  N   UNK     0       6.744   2.498   0.000  0.00  0.00           N+0
HETATM   17  C   UNK     0       7.142   0.823   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       8.753   0.164   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       5.819  -0.080   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       4.293   0.343   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       3.955   1.876   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       5.173   2.875   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       8.539   1.283   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       9.903   0.568   0.000  0.00  0.00           O+0
HETATM   25  N   UNK     0       8.141   2.632   0.000  0.00  0.00           N+0
HETATM   26  C   UNK     0       6.775   3.343   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      12.885   0.796   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      11.683   0.007   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0      17.275   3.099   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0      18.791   2.827   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      19.523   1.472   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      18.920   0.055   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0      17.437  -0.358   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0      20.351  -0.516   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      19.299  -1.438   0.000  0.00  0.00           C+0
CONECT    1    2    6                                                       
CONECT    2    1    3   33                                                  
CONECT    3    2    4   29                                                  
CONECT    4    3    5   10                                                  
CONECT    5    4    6    7                                                  
CONECT    6    5    1                                                       
CONECT    7    5    8   11   14                                             
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8    4                                                       
CONECT   11    7   12   27   28                                             
CONECT   12   11   13   18                                                  
CONECT   13   12   14   15   25                                             
CONECT   14   13    7                                                       
CONECT   15   13   16                                                       
CONECT   16   15   17   22                                                  
CONECT   17   16   18   19   23                                             
CONECT   18   17   12                                                       
CONECT   19   17   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   16                                                       
CONECT   23   17   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23   13   26                                                  
CONECT   26   25                                                            
CONECT   27   11                                                            
CONECT   28   11                                                            
CONECT   29    3   30                                                       
CONECT   30   29   31                                                       
CONECT   31   30   32                                                       
CONECT   32   31   33   34   35                                             
CONECT   33   32    2                                                       
CONECT   34   32                                                            
CONECT   35   32                                                            
MASTER        0    0    0    0    0    0    0    0   35    0   82    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₈H₃₅N₃O₄

Average Mass

477.6050 Da

Monoisotopic Mass

477.26276 Da

IUPAC Name

(1'S,8R,8'S,10'S)-4,4,11',11',14'-pentamethyl-9,10-dihydro-4H-3',14'-diazaspiro[[1,4]dioxepino[2,3-g]indole-8,12'-tetracyclo[6.5.2.0^{1,10}.0^{3,8}]pentadecane]-9,15'-dione

Traditional Name

(1'S,8R,8'S,10'S)-4,4,11',11',14'-pentamethyl-10H-3',14'-diazaspiro[[1,4]dioxepino[2,3-g]indole-8,12'-tetracyclo[6.5.2.0^{1,10}.0^{3,8}]pentadecane]-9,15'-dione

CAS Registry Number

Not Available

SMILES

CN1C(=O)[C@@]23CCCCN2C[C@@]11C[C@@]2(C(=O)NC4=C5OC=CC(C)(C)OC5=CC=C24)C(C)(C)[C@@H]1C3

InChI Identifier

InChI=1S/C28H35N3O4/c1-24(2)11-13-34-21-18(35-24)9-8-17-20(21)29-22(32)28(17)15-27-16-31-12-7-6-10-26(31,23(33)30(27)5)14-19(27)25(28,3)4/h8-9,11,13,19H,6-7,10,12,14-16H2,1-5H3,(H,29,32)/t19-,26-,27+,28+/m0/s1

InChI Key

KYKUTNUWXQVSSU-ZALBMCOMSA-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, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, 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
Aspergillus carneus	LOTUS Database	35616633
Penicillium roqueforti	Fungi	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as piperazinopiperidines. These are organic aromatic compounds containing a piperazine ring fused to a piperidine.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Piperazinopiperidines

Sub Class

Not Available

Direct Parent

Piperazinopiperidines

Alternative Parents

Substituents

Alpha-amino acid or derivatives
Azaspirodecane
Piperazino-1,2-a-piperidine
Quinolizidine
Indole or derivatives
Dihydroindole
1,4-dioxepine
Alkyl aryl ether
Delta-lactam
Dioxepine
Aralkylamine
N-alkylpiperazine
N-methylpiperazine
Piperidinone
1,4-diazinane
Benzenoid
Piperazine
Piperidine
Tertiary carboxylic acid amide
Secondary carboxylic acid amide
Tertiary amine
Lactam
Tertiary aliphatic amine
Amino acid or derivatives
Carboxamide group
Ether
Carboxylic acid derivative
Oxacycle
Azacycle
Organic oxide
Carbonyl group
Hydrocarbon derivative
Organic oxygen compound
Organooxygen compound
Amine
Organic nitrogen compound
Organonitrogen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic 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	4.05	ALOGPS
logP	2.92	ChemAxon
logS	-3.7	ALOGPS
pKa (Strongest Acidic)	11.59	ChemAxon
pKa (Strongest Basic)	6.15	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	71.11 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	133.56 m³·mol⁻¹	ChemAxon
Polarizability	52.49 Å³	ChemAxon
Number of Rings	7	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

C00023600

Chemspider ID

9158840

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

10983639

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Capon RJ, Skene C, Stewart M, Ford J, O'Hair RA, Williams L, Lacey E, Gill JH, Heiland K, Friedel T: Aspergillicins A-E: five novel depsipeptides from the marine-derived fungus Aspergillus carneus. Org Biomol Chem. 2003 Jun 7;1(11):1856-62. doi: 10.1039/b302306k. [PubMed:12945765 ]
Penagos-Tabares F, Khiaosa-Ard R, Schmidt M, Pacifico C, Faas J, Jenkins T, Nagl V, Sulyok M, Labuda R, Zebeli Q: Fungal species and mycotoxins in mouldy spots of grass and maize silages in Austria. Mycotoxin Res. 2022 May;38(2):117-136. doi: 10.1007/s12550-022-00453-3. Epub 2022 Mar 26. [PubMed:35347677 ]
Dagnac T, Latorre A, Fernandez Lorenzo B, Llompart M: Validation and application of a liquid chromatography-tandem mass spectrometry based method for the assessment of the co-occurrence of mycotoxins in maize silages from dairy farms in NW Spain. Food Addit Contam Part A Chem Anal Control Expo Risk Assess. 2016 Dec;33(12):1850-1863. doi: 10.1080/19440049.2016.1243806. Epub 2016 Oct 26. [PubMed:27707355 ]
Rasmussen RR, Storm IM, Rasmussen PH, Smedsgaard J, Nielsen KF: Multi-mycotoxin analysis of maize silage by LC-MS/MS. Anal Bioanal Chem. 2010 May;397(2):765-76. doi: 10.1007/s00216-010-3545-7. Epub 2010 Mar 6. [PubMed:20213172 ]
O'Brien M, Nielsen KF, O'Kiely P, Forristal PD, Fuller HT, Frisvad JC: Mycotoxins and other secondary metabolites produced in vitro by Penicillium paneum Frisvad and Penicillium roqueforti Thom isolated from baled grass silage in Ireland. J Agric Food Chem. 2006 Nov 29;54(24):9268-76. doi: 10.1021/jf0621018. [PubMed:17117820 ]

Showing NP-Card for Marcfortine A (NP0066247)

MOL for NP0066247 (Marcfortine A)

3D MOL for NP0066247 (Marcfortine A)

3D SDF for NP0066247 (Marcfortine A)

3D-SDF for NP0066247 (Marcfortine A)

PDB for NP0066247 (Marcfortine A)

3D PDB for NP0066247 (Marcfortine A)

SMILES for NP0066247 (Marcfortine A)

INCHI for NP0066247 (Marcfortine A)

Structure for NP0066247 (Marcfortine A)

3D Structure for NP0066247 (Marcfortine A)