NP-MRD: Showing NP-Card for methyl (4ar,5s,8ar)-3,5-dihydroxy-2-methylidene-4a,5,6,8a-tetrahydro-1,4-benzoxazine-7-carboxylate (NP0315109)

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Record Information

Version

2.0

Created at

2022-09-11 13:34:54 UTC

Updated at

2022-09-11 13:34:54 UTC

NP-MRD ID

NP0315109

Secondary Accession Numbers

None

Natural Product Identification

Common Name

methyl (4ar,5s,8ar)-3,5-dihydroxy-2-methylidene-4a,5,6,8a-tetrahydro-1,4-benzoxazine-7-carboxylate

Description

Monocillinol B 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). Based on a literature review very few articles have been published on monocillinol B.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 30 31  0  0  0  0  0  0  0  0999 V2000
   -4.0791    1.6200    0.2280 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0966    0.7634    0.0654 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7668    1.2134   -0.0768 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7974    0.2943    0.3952 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.5876    0.7074    0.1824 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5843   -0.1091   -0.1594 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9111    0.4714   -0.3318 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8582   -0.2862   -0.6535 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1816    1.8074   -0.1607 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4936    2.3542   -0.3358 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3763   -1.5663   -0.3646 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0755   -1.9447    0.3079 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.2267   -3.2803    0.1862 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9885   -1.0396   -0.2867 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.3151   -1.5210   -0.1434 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2884   -0.6958    0.0182 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5913   -1.1941    0.1564 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1003    1.2630    0.3367 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8811    2.6632    0.2536 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9184    0.1167    1.5036 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8271    1.7526    0.3105 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9142    2.0844   -1.3267 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1807    2.0163    0.4447 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4254    3.4597   -0.3220 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2480   -1.8015   -1.4524 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2298   -2.1654    0.0069 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1928   -1.7213    1.3939 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1161   -3.6502   -0.7102 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7173   -0.8783   -1.3665 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2032   -0.7334    0.8047 H   0  0  0  0  0  0  0  0  0  0  0  0
 10  9  1  0
  9  7  1  0
  7  8  2  0
  7  6  1  0
  6  5  2  0
  5  4  1  0
  4  3  1  0
  3  2  1  0
  2  1  2  3
  2 16  1  0
 16 17  1  0
 16 15  2  0
 15 14  1  0
 14 12  1  0
 12 13  1  0
 12 11  1  0
 11  6  1  0
 14  4  1  0
 10 22  1  0
 10 23  1  0
 10 24  1  0
  5 21  1  0
  4 20  1  1
  1 18  1  0
  1 19  1  0
 17 30  1  0
 14 29  1  6
 12 27  1  1
 13 28  1  0
 11 25  1  0
 11 26  1  0
M  END


  Mrv1652309112215342D          

 17 18  0  0  1  0            999 V2000
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.8579   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  4  3  1  6  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  7  9  1  0  0  0  0
  9 10  1  0  0  0  0
  6 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  6  0  0  0
 12 14  1  0  0  0  0
  4 14  1  0  0  0  0
 14 15  1  1  0  0  0
 15 16  2  0  0  0  0
  2 16  1  0  0  0  0
 16 17  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0315109

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC(=O)C1=C[C@H]2OC(=C)C(O)=N[C@@H]2[C@@H](O)C1

> <INCHI_IDENTIFIER>
InChI=1S/C11H13NO5/c1-5-10(14)12-9-7(13)3-6(11(15)16-2)4-8(9)17-5/h4,7-9,13H,1,3H2,2H3,(H,12,14)/t7-,8+,9+/m0/s1

> <INCHI_KEY>
MRTLVFNBTBKYFV-DJLDLDEBSA-N

> <FORMULA>
C11H13NO5

> <MOLECULAR_WEIGHT>
239.227

> <EXACT_MASS>
239.079372523

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
30

> <JCHEM_AVERAGE_POLARIZABILITY>
23.572615892202265

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
methyl (4aR,5S,8aR)-3,5-dihydroxy-2-methylidene-4a,5,6,8a-tetrahydro-2H-1,4-benzoxazine-7-carboxylate

> <JCHEM_LOGP>
0.1397620293333332

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.415266884492222

> <JCHEM_PKA_STRONGEST_ACIDIC>
5.616551002076058

> <JCHEM_PKA_STRONGEST_BASIC>
1.28404580023142

> <JCHEM_POLAR_SURFACE_AREA>
88.35000000000002

> <JCHEM_REFRACTIVITY>
58.457400000000014

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
methyl (4aR,5S,8aR)-3,5-dihydroxy-2-methylidene-4a,5,6,8a-tetrahydro-1,4-benzoxazine-7-carboxylate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 11-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   11-SEP-22         0                                  
HETATM    1  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       2.667   0.000   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       8.002  -0.000   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       8.002   1.540   0.000  0.00  0.00           O+0
HETATM    9  O   UNK     0       9.336  -0.770   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0      10.669  -0.000   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       5.335  -4.620   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   15  N   UNK     0       2.667  -3.080   0.000  0.00  0.00           N+0
HETATM   16  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       0.000  -3.080   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   16                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5   14                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7   11                                                  
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10                                                       
CONECT   10    9                                                            
CONECT   11    6   12                                                       
CONECT   12   11   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12    4   15                                                  
CONECT   15   14   16                                                       
CONECT   16   15    2   17                                                  
CONECT   17   16                                                            
MASTER        0    0    0    0    0    0    0    0   17    0   36    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₁H₁₃NO₅

Average Mass

239.2270 Da

Monoisotopic Mass

239.07937 Da

IUPAC Name

methyl (4aR,5S,8aR)-3,5-dihydroxy-2-methylidene-4a,5,6,8a-tetrahydro-2H-1,4-benzoxazine-7-carboxylate

Traditional Name

methyl (4aR,5S,8aR)-3,5-dihydroxy-2-methylidene-4a,5,6,8a-tetrahydro-1,4-benzoxazine-7-carboxylate

CAS Registry Number

Not Available

SMILES

COC(=O)C1=C[C@H]2OC(=C)C(O)=N[C@@H]2[C@@H](O)C1

InChI Identifier

InChI=1S/C11H13NO5/c1-5-10(14)12-9-7(13)3-6(11(15)16-2)4-8(9)17-5/h4,7-9,13H,1,3H2,2H3,(H,12,14)/t7-,8+,9+/m0/s1

InChI Key

MRTLVFNBTBKYFV-DJLDLDEBSA-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 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
Para-oxazine
Methyl ester
Enoate ester
Alpha,beta-unsaturated carboxylic ester
Cyclic carboximidic acid
Carboxylic acid ester
Secondary alcohol
Organic 1,3-dipolar compound
Propargyl-type 1,3-dipolar organic compound
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Oxacycle
Azacycle
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Alcohol
Organooxygen compound
Organonitrogen compound
Organic nitrogen compound
Carbonyl group
Organic oxygen compound
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic 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	0.14	ChemAxon
pKa (Strongest Acidic)	5.62	ChemAxon
pKa (Strongest Basic)	1.28	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	88.35 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	58.46 m³·mol⁻¹	ChemAxon
Polarizability	23.57 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	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

78436131

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

139583162

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for methyl (4ar,5s,8ar)-3,5-dihydroxy-2-methylidene-4a,5,6,8a-tetrahydro-1,4-benzoxazine-7-carboxylate (NP0315109)

MOL for NP0315109 (methyl (4ar,5s,8ar)-3,5-dihydroxy-2-methylidene-4a,5,6,8a-tetrahydro-1,4-benzoxazine-7-carboxylate)

3D MOL for NP0315109 (methyl (4ar,5s,8ar)-3,5-dihydroxy-2-methylidene-4a,5,6,8a-tetrahydro-1,4-benzoxazine-7-carboxylate)

3D SDF for NP0315109 (methyl (4ar,5s,8ar)-3,5-dihydroxy-2-methylidene-4a,5,6,8a-tetrahydro-1,4-benzoxazine-7-carboxylate)

3D-SDF for NP0315109 (methyl (4ar,5s,8ar)-3,5-dihydroxy-2-methylidene-4a,5,6,8a-tetrahydro-1,4-benzoxazine-7-carboxylate)

PDB for NP0315109 (methyl (4ar,5s,8ar)-3,5-dihydroxy-2-methylidene-4a,5,6,8a-tetrahydro-1,4-benzoxazine-7-carboxylate)

3D PDB for NP0315109 (methyl (4ar,5s,8ar)-3,5-dihydroxy-2-methylidene-4a,5,6,8a-tetrahydro-1,4-benzoxazine-7-carboxylate)

SMILES for NP0315109 (methyl (4ar,5s,8ar)-3,5-dihydroxy-2-methylidene-4a,5,6,8a-tetrahydro-1,4-benzoxazine-7-carboxylate)

INCHI for NP0315109 (methyl (4ar,5s,8ar)-3,5-dihydroxy-2-methylidene-4a,5,6,8a-tetrahydro-1,4-benzoxazine-7-carboxylate)

Structure for NP0315109 (methyl (4ar,5s,8ar)-3,5-dihydroxy-2-methylidene-4a,5,6,8a-tetrahydro-1,4-benzoxazine-7-carboxylate)

3D Structure for NP0315109 (methyl (4ar,5s,8ar)-3,5-dihydroxy-2-methylidene-4a,5,6,8a-tetrahydro-1,4-benzoxazine-7-carboxylate)