NP-MRD: Showing NP-Card for ({[3-ethyl-6,9,11,15-tetrahydroxy-7-isopropyl-3-methyl-10-(methylamino)-2-oxa-5,8-diazabicyclo[10.3.1]hexadeca-1(16),5,8,12,14-pentaen-4-yl](hydroxy)methylidene}amino)acetic acid (NP0273333)

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Record Information

Version

1.0

Created at

2022-09-08 20:19:58 UTC

Updated at

2022-09-08 20:19:59 UTC

NP-MRD ID

NP0273333

Secondary Accession Numbers

None

Natural Product Identification

Common Name

({[3-ethyl-6,9,11,15-tetrahydroxy-7-isopropyl-3-methyl-10-(methylamino)-2-oxa-5,8-diazabicyclo[10.3.1]hexadeca-1(16),5,8,12,14-pentaen-4-yl](hydroxy)methylidene}amino)acetic acid

Description

Ustiloxin D belongs to the class of organic compounds known as cyclic peptides. Cyclic peptides are compounds containing a cyclic moiety bearing a peptide backbone. Ustiloxin D is a very strong basic compound (based on its pKa). Outside of the human body, Ustiloxin D has been detected, but not quantified in, cereals and cereal products. ({[3-ethyl-6,9,11,15-tetrahydroxy-7-isopropyl-3-methyl-10-(methylamino)-2-oxa-5,8-diazabicyclo[10.3.1]hexadeca-1(16),5,8,12,14-pentaen-4-yl](hydroxy)methylidene}amino)acetic acid is found in Ustilaginoidea virens. This could make ustiloxin D a potential biomarker for the consumption of these foods.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv0541 05061312212D          

 35 36  0  0  0  0            999 V2000
    0.3216   -1.3247    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9739   -1.8298    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7190   -2.6145    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.3624    0.1913    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0210    0.7176    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3031    1.4928    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7728    2.1248    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8457   -1.7418    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.3609   -1.8298    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1060   -2.6145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    1.7354    1.1301    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4499   -0.1074    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.1644    0.3051    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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M  END

     RDKit          3D

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M  END


  Mrv0541 05061312212D          

 35 36  0  0  0  0            999 V2000
    0.3216   -1.3247    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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  1 35  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0273333

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCC1(C)OC2=CC(=CC=C2O)C(O)C(NC)C(=O)NC(C(C)C)C(=O)NC1C(=O)NCC(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C23H34N4O8/c1-6-23(4)19(22(34)25-10-15(29)30)27-20(32)16(11(2)3)26-21(33)17(24-5)18(31)12-7-8-13(28)14(9-12)35-23/h7-9,11,16-19,24,28,31H,6,10H2,1-5H3,(H,25,34)(H,26,33)(H,27,32)(H,29,30)

> <INCHI_KEY>
GDXLZSYACWZHOC-UHFFFAOYSA-N

> <FORMULA>
C23H34N4O8

> <MOLECULAR_WEIGHT>
494.5381

> <EXACT_MASS>
494.237664084

> <JCHEM_ACCEPTOR_COUNT>
9

> <JCHEM_AVERAGE_POLARIZABILITY>
49.26868909544456

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
7

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-{[3-ethyl-11,15-dihydroxy-3-methyl-10-(methylamino)-6,9-dioxo-7-(propan-2-yl)-2-oxa-5,8-diazabicyclo[10.3.1]hexadeca-1(16),12,14-trien-4-yl]formamido}acetic acid

> <ALOGPS_LOGP>
0.06

> <JCHEM_LOGP>
-2.943018955571866

> <ALOGPS_LOGS>
-2.46

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.768794739906959

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.080488970363915

> <JCHEM_PKA_STRONGEST_BASIC>
7.690191001444652

> <JCHEM_POLAR_SURFACE_AREA>
186.32

> <JCHEM_REFRACTIVITY>
122.79979999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.71e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
{[3-ethyl-11,15-dihydroxy-7-isopropyl-3-methyl-10-(methylamino)-6,9-dioxo-2-oxa-5,8-diazabicyclo[10.3.1]hexadeca-1(16),12,14-trien-4-yl]formamido}acetic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 06-MAY-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAY-13         0                                  
HETATM    1  C   UNK     0       0.600  -2.473   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.818  -3.416   0.000  0.00  0.00           C+0
HETATM    3  N   UNK     0       1.342  -4.880   0.000  0.00  0.00           N+0
HETATM    4  C   UNK     0       0.676   0.357   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.906   1.340   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.432   2.787   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.443   3.966   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0      -3.445  -3.251   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0      -2.095  -2.510   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -0.674  -3.416   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -0.198  -4.880   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      -1.103  -6.126   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0      -3.372  -4.106   0.000  0.00  0.00           C+0
HETATM   14  N   UNK     0      -1.891  -4.359   0.000  0.00  0.00           N+0
HETATM   15  O   UNK     0      -2.095   3.650   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0      -2.095   2.110   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -3.429   1.340   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -3.429  -0.200   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -2.095  -0.970   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -0.762  -0.200   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -0.762   1.340   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       0.572   2.110   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0       4.590  -3.251   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0       3.239  -2.510   0.000  0.00  0.00           C+0
HETATM   25  N   UNK     0       3.239  -0.970   0.000  0.00  0.00           N+0
HETATM   26  C   UNK     0       1.906  -0.200   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       3.239   0.570   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0       3.239   2.110   0.000  0.00  0.00           O+0
HETATM   29  N   UNK     0       4.573  -0.200   0.000  0.00  0.00           N+0
HETATM   30  C   UNK     0       5.907   0.570   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       7.240  -0.200   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0       8.574   0.570   0.000  0.00  0.00           O+0
HETATM   33  O   UNK     0       7.240  -1.740   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0       1.228  -1.067   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      -0.881  -2.202   0.000  0.00  0.00           C+0
CONECT    1    2   34   35                                                  
CONECT    2    1    3   24                                                  
CONECT    3    2   11                                                       
CONECT    4    5                                                            
CONECT    5    4    6   22   26                                             
CONECT    6    5    7                                                       
CONECT    7    6                                                            
CONECT    8    9                                                            
CONECT    9    8   10   19                                                  
CONECT   10    9   11   14                                                  
CONECT   11    3   10   12                                                  
CONECT   12   11                                                            
CONECT   13   14                                                            
CONECT   14   10   13                                                       
CONECT   15   16                                                            
CONECT   16   15   17   21                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19    9   18   20                                                  
CONECT   20   19   21                                                       
CONECT   21   16   20   22                                                  
CONECT   22    5   21                                                       
CONECT   23   24                                                            
CONECT   24    2   23   25                                                  
CONECT   25   24   26                                                       
CONECT   26    5   25   27                                                  
CONECT   27   26   28   29                                                  
CONECT   28   27                                                            
CONECT   29   27   30                                                       
CONECT   30   29   31                                                       
CONECT   31   30   32   33                                                  
CONECT   32   31                                                            
CONECT   33   31                                                            
CONECT   34    1                                                            
CONECT   35    1                                                            
MASTER        0    0    0    0    0    0    0    0   35    0   72    0
END

View in JSmol

Synonyms

Value	Source
2-({[3-ethyl-6,9,11,15-tetrahydroxy-3-methyl-10-(methylamino)-7-(propan-2-yl)-2-oxa-5,8-diazabicyclo[10.3.1]hexadeca-1(15),5,8,12(16),13-pentaen-4-yl](hydroxy)methylidene}amino)acetate	Generator

Chemical Formula

C₂₃H₃₄N₄O₈

Average Mass

494.5381 Da

Monoisotopic Mass

494.23766 Da

IUPAC Name

2-{[3-ethyl-11,15-dihydroxy-3-methyl-10-(methylamino)-6,9-dioxo-7-(propan-2-yl)-2-oxa-5,8-diazabicyclo[10.3.1]hexadeca-1(16),12,14-trien-4-yl]formamido}acetic acid

Traditional Name

{[3-ethyl-11,15-dihydroxy-7-isopropyl-3-methyl-10-(methylamino)-6,9-dioxo-2-oxa-5,8-diazabicyclo[10.3.1]hexadeca-1(16),12,14-trien-4-yl]formamido}acetic acid

CAS Registry Number

Not Available

SMILES

CCC1(C)OC2=CC(=CC=C2O)C(O)C(NC)C(=O)NC(C(C)C)C(=O)NC1C(=O)NCC(O)=O

InChI Identifier

InChI=1S/C23H34N4O8/c1-6-23(4)19(22(34)25-10-15(29)30)27-20(32)16(11(2)3)26-21(33)17(24-5)18(31)12-7-8-13(28)14(9-12)35-23/h7-9,11,16-19,24,28,31H,6,10H2,1-5H3,(H,25,34)(H,26,33)(H,27,32)(H,29,30)

InChI Key

GDXLZSYACWZHOC-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

Species Name	Source	Reference
Ustilaginoidea virens	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as cyclic peptides. Cyclic peptides are compounds containing a cyclic moiety bearing a peptide backbone.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

Cyclic peptides

Alternative Parents

Substituents

Cyclic alpha peptide
N-acyl-alpha-amino acid
N-acyl-alpha amino acid or derivatives
Alpha-amino acid or derivatives
Alkyl aryl ether
1-hydroxy-2-unsubstituted benzenoid
Aralkylamine
Benzenoid
Cyclic carboximidic acid
Amino acid or derivatives
Amino acid
Secondary alcohol
Carboximidic acid
Carboximidic acid derivative
Carboxylic acid
Secondary aliphatic amine
Ether
Monocarboxylic acid or derivatives
Oxacycle
Polyol
Azacycle
Secondary amine
Organoheterocyclic compound
Organic 1,3-dipolar compound
Propargyl-type 1,3-dipolar organic compound
Hydrocarbon derivative
Carbonyl group
Organonitrogen compound
Organooxygen compound
Alcohol
Organic nitrogen compound
Organic oxygen compound
Organic oxide
Amine
Organopnictogen 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	0.06	ALOGPS
logP	-2.9	ChemAxon
logS	-2.5	ALOGPS
pKa (Strongest Acidic)	3.08	ChemAxon
pKa (Strongest Basic)	7.69	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	9	ChemAxon
Hydrogen Donor Count	7	ChemAxon
Polar Surface Area	186.32 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	122.8 m³·mol⁻¹	ChemAxon
Polarizability	49.27 Å³	ChemAxon
Number of Rings	2	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

HMDB0041054

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB020928

KNApSAcK ID

C00016649

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

72773471

PDB ID

Not Available

ChEBI ID

458649

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for ({[3-ethyl-6,9,11,15-tetrahydroxy-7-isopropyl-3-methyl-10-(methylamino)-2-oxa-5,8-diazabicyclo[10.3.1]hexadeca-1(16),5,8,12,14-pentaen-4-yl](hydroxy)methylidene}amino)acetic acid (NP0273333)

MOL for NP0273333 (({[3-ethyl-6,9,11,15-tetrahydroxy-7-isopropyl-3-methyl-10-(methylamino)-2-oxa-5,8-diazabicyclo[10.3.1]hexadeca-1(16),5,8,12,14-pentaen-4-yl](hydroxy)methylidene}amino)acetic acid)

3D MOL for NP0273333 (({[3-ethyl-6,9,11,15-tetrahydroxy-7-isopropyl-3-methyl-10-(methylamino)-2-oxa-5,8-diazabicyclo[10.3.1]hexadeca-1(16),5,8,12,14-pentaen-4-yl](hydroxy)methylidene}amino)acetic acid)

3D SDF for NP0273333 (({[3-ethyl-6,9,11,15-tetrahydroxy-7-isopropyl-3-methyl-10-(methylamino)-2-oxa-5,8-diazabicyclo[10.3.1]hexadeca-1(16),5,8,12,14-pentaen-4-yl](hydroxy)methylidene}amino)acetic acid)

3D-SDF for NP0273333 (({[3-ethyl-6,9,11,15-tetrahydroxy-7-isopropyl-3-methyl-10-(methylamino)-2-oxa-5,8-diazabicyclo[10.3.1]hexadeca-1(16),5,8,12,14-pentaen-4-yl](hydroxy)methylidene}amino)acetic acid)

PDB for NP0273333 (({[3-ethyl-6,9,11,15-tetrahydroxy-7-isopropyl-3-methyl-10-(methylamino)-2-oxa-5,8-diazabicyclo[10.3.1]hexadeca-1(16),5,8,12,14-pentaen-4-yl](hydroxy)methylidene}amino)acetic acid)

3D PDB for NP0273333 (({[3-ethyl-6,9,11,15-tetrahydroxy-7-isopropyl-3-methyl-10-(methylamino)-2-oxa-5,8-diazabicyclo[10.3.1]hexadeca-1(16),5,8,12,14-pentaen-4-yl](hydroxy)methylidene}amino)acetic acid)

SMILES for NP0273333 (({[3-ethyl-6,9,11,15-tetrahydroxy-7-isopropyl-3-methyl-10-(methylamino)-2-oxa-5,8-diazabicyclo[10.3.1]hexadeca-1(16),5,8,12,14-pentaen-4-yl](hydroxy)methylidene}amino)acetic acid)

INCHI for NP0273333 (({[3-ethyl-6,9,11,15-tetrahydroxy-7-isopropyl-3-methyl-10-(methylamino)-2-oxa-5,8-diazabicyclo[10.3.1]hexadeca-1(16),5,8,12,14-pentaen-4-yl](hydroxy)methylidene}amino)acetic acid)

Structure for NP0273333 (({[3-ethyl-6,9,11,15-tetrahydroxy-7-isopropyl-3-methyl-10-(methylamino)-2-oxa-5,8-diazabicyclo[10.3.1]hexadeca-1(16),5,8,12,14-pentaen-4-yl](hydroxy)methylidene}amino)acetic acid)

3D Structure for NP0273333 (({[3-ethyl-6,9,11,15-tetrahydroxy-7-isopropyl-3-methyl-10-(methylamino)-2-oxa-5,8-diazabicyclo[10.3.1]hexadeca-1(16),5,8,12,14-pentaen-4-yl](hydroxy)methylidene}amino)acetic acid)