NP-MRD: Showing NP-Card for Zeanoside C (NP0049269)

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Record Information

Version

1.0

Created at

2022-03-17 21:09:46 UTC

Updated at

2022-03-17 21:09:46 UTC

NP-MRD ID

NP0049269

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Zeanoside C

Description

Zeanoside C belongs to the class of organic compounds known as benzoxazines. These are organic compounds containing a benzene fused to an oxazine ring (a six-membered aliphatic ring with four carbon atoms, one oxygen atom, and one nitrogen atom). Zeanoside C is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, Zeanoside C is found, on average, in the highest concentration within corns. Zeanoside C has also been detected, but not quantified in, cereals and cereal products and fats and oils. Zeanoside C is found in Zea mays. This could make zeanoside C a potential biomarker for the consumption of these foods.

Structure

MOL SDF PDB SMILES InChI


  Mrv0541 02241212032D          

 27 29  0  0  0  0            999 V2000
    1.1681    0.9237    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5976    0.2987    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2768   -0.2444    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0648   -0.0542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6082   -0.7063    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4451    0.7063    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1901    1.7659    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0814    0.9237    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7065    0.6791    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7065   -0.1357    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0814   -0.3803    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2716   -1.1953    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3534   -1.7659    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1681   -1.5214    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3312   -0.7063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1463   -0.4346    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1463    0.2987    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9018    0.4346    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9018    0.7063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6844    0.8421    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6844    1.1138    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6082    0.2987    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3636    0.4346    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3636    0.7063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1463    0.8421    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1463    1.1138    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6082    0.8421    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
  2  8  1  0  0  0  0
  2 11  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  4  6  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 10 15  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 17 23  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 19 25  1  0  0  0  0
 20 21  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 24 27  1  0  0  0  0
 25 26  1  0  0  0  0
M  END


  Mrv0541 02241212032D          

 27 29  0  0  0  0            999 V2000
    1.1681    0.9237    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5976    0.2987    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2768   -0.2444    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0648   -0.0542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6082   -0.7063    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4451    0.7063    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1901    1.7659    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0814    0.9237    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7065    0.6791    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7065   -0.1357    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0814   -0.3803    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2716   -1.1953    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3534   -1.7659    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1681   -1.5214    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3312   -0.7063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1463   -0.4346    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1463    0.2987    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9018    0.4346    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9018    0.7063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6844    0.8421    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6844    1.1138    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6082    0.2987    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3636    0.4346    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3636    0.7063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1463    0.8421    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1463    1.1138    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6082    0.8421    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
  2  8  1  0  0  0  0
  2 11  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  4  6  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 10 15  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 17 23  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 19 25  1  0  0  0  0
 20 21  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 24 27  1  0  0  0  0
 25 26  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0049269

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OCC1OC(OC2=CC=CC3=C2NC(=O)C3(O)CC(O)=O)C(O)C(O)C1O

> <INCHI_IDENTIFIER>
InChI=1S/C16H19NO10/c18-5-8-11(21)12(22)13(23)14(27-8)26-7-3-1-2-6-10(7)17-15(24)16(6,25)4-9(19)20/h1-3,8,11-14,18,21-23,25H,4-5H2,(H,17,24)(H,19,20)

> <INCHI_KEY>
VNIXZLMYLWKZLU-UHFFFAOYSA-N

> <FORMULA>
C16H19NO10

> <MOLECULAR_WEIGHT>
385.3228

> <EXACT_MASS>
385.100895833

> <JCHEM_ACCEPTOR_COUNT>
10

> <JCHEM_AVERAGE_POLARIZABILITY>
35.17000761829551

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
7

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-(3-hydroxy-2-oxo-7-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-2,3-dihydro-1H-indol-3-yl)acetic acid

> <ALOGPS_LOGP>
-1.59

> <JCHEM_LOGP>
-2.4237877126666665

> <ALOGPS_LOGS>
-1.05

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
10.917122093840883

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.3875371452996292

> <JCHEM_PKA_STRONGEST_BASIC>
-2.981092350576362

> <JCHEM_POLAR_SURFACE_AREA>
186.01

> <JCHEM_REFRACTIVITY>
85.7971

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
3.42e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(3-hydroxy-2-oxo-7-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1H-indol-3-yl)acetic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  O   UNK     0       2.180   1.724   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       1.116   0.558   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.383  -0.456   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       3.854  -0.101   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0       4.869  -1.318   0.000  0.00  0.00           O+0
HETATM    6  O   UNK     0       4.564   1.318   0.000  0.00  0.00           O+0
HETATM    7  O   UNK     0       0.355   3.296   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       0.152   1.724   0.000  0.00  0.00           C+0
HETATM    9  N   UNK     0      -1.319   1.268   0.000  0.00  0.00           N+0
HETATM   10  C   UNK     0      -1.319  -0.253   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.152  -0.710   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       0.507  -2.231   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -0.660  -3.296   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -2.180  -2.840   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -2.485  -1.318   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      -4.006  -0.811   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0      -4.006   0.558   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      -3.550   0.811   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0      -3.550   1.318   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -3.144   1.572   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      -3.144   2.079   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0      -4.869   0.558   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0      -4.412   0.811   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      -4.412   1.318   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      -4.006   1.572   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0      -4.006   2.079   0.000  0.00  0.00           O+0
HETATM   27  O   UNK     0      -4.869   1.572   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    8   11                                             
CONECT    3    2    4                                                       
CONECT    4    3    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4                                                            
CONECT    7    8                                                            
CONECT    8    2    7    9                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11   15                                                  
CONECT   11    2   10   12                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   10   14   16                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18   23                                                  
CONECT   18   17   19                                                       
CONECT   19   18   20   25                                                  
CONECT   20   19   21                                                       
CONECT   21   20                                                            
CONECT   22   23                                                            
CONECT   23   17   22   24                                                  
CONECT   24   23   25   27                                                  
CONECT   25   19   24   26                                                  
CONECT   26   25                                                            
CONECT   27   24                                                            
MASTER        0    0    0    0    0    0    0    0   27    0   58    0
END

View in JSmol

Synonyms

Value	Source
2-(2,3-Dihydroxy-7-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3H-indol-3-yl)acetate	Generator

Chemical Formula

C₁₆H₁₉NO₁₀

Average Mass

385.3228 Da

Monoisotopic Mass

385.10090 Da

IUPAC Name

2-(3-hydroxy-2-oxo-7-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-2,3-dihydro-1H-indol-3-yl)acetic acid

Traditional Name

(3-hydroxy-2-oxo-7-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1H-indol-3-yl)acetic acid

CAS Registry Number

120293-55-2

SMILES

OCC1OC(OC2=CC=CC3=C2NC(=O)C3(O)CC(O)=O)C(O)C(O)C1O

InChI Identifier

InChI=1S/C16H19NO10/c18-5-8-11(21)12(22)13(23)14(27-8)26-7-3-1-2-6-10(7)17-15(24)16(6,25)4-9(19)20/h1-3,8,11-14,18,21-23,25H,4-5H2,(H,17,24)(H,19,20)

InChI Key

VNIXZLMYLWKZLU-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Zea mays	LOTUS Database	35616633
Zea mays L.	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as benzoxazines. These are organic compounds containing a benzene fused to an oxazine ring (a six-membered aliphatic ring with four carbon atoms, one oxygen atom, and one nitrogen atom).

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Benzoxazines

Sub Class

Not Available

Direct Parent

Benzoxazines

Alternative Parents

Substituents

Benzoxazine
Styrene
1-hydroxy-2-unsubstituted benzenoid
Phenol
Monocyclic benzene moiety
Benzenoid
Heteroaromatic compound
Lactone
Oxacycle
Azacycle
Organic nitrogen compound
Hydrocarbon derivative
Organic oxide
Organooxygen compound
Organonitrogen compound
Organopnictogen compound
Organic oxygen 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	-1.6	ALOGPS
logP	-2.4	ChemAxon
logS	-1	ALOGPS
pKa (Strongest Acidic)	3.39	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	10	ChemAxon
Hydrogen Donor Count	7	ChemAxon
Polar Surface Area	186.01 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	85.8 m³·mol⁻¹	ChemAxon
Polarizability	35.17 Å³	ChemAxon
Number of Rings	3	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

HMDB0038960

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB018444

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

13988324

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Zeanoside C (NP0049269)

MOL for NP0049269 (Zeanoside C)

3D MOL for NP0049269 (Zeanoside C)

3D SDF for NP0049269 (Zeanoside C)

3D-SDF for NP0049269 (Zeanoside C)

PDB for NP0049269 (Zeanoside C)

3D PDB for NP0049269 (Zeanoside C)

SMILES for NP0049269 (Zeanoside C)

INCHI for NP0049269 (Zeanoside C)

Structure for NP0049269 (Zeanoside C)

3D Structure for NP0049269 (Zeanoside C)