NP-MRD: Showing NP-Card for l-dihydroanticapsin (NP0287060)

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Record Information

Version

2.0

Created at

2022-09-09 15:56:28 UTC

Updated at

2022-09-09 15:56:28 UTC

NP-MRD ID

NP0287060

Secondary Accession Numbers

None

Natural Product Identification

Common Name

l-dihydroanticapsin

Description

L-dihydroanticapsin zwitterion, also known as L-dihydroanticapsin, belongs to the class of organic compounds known as l-alpha-amino acids. These are alpha amino acids which have the L-configuration of the alpha-carbon atom. l-dihydroanticapsin is found in Apis cerana. L-dihydroanticapsin zwitterion is a very strong basic compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 29 30  0  0  0  0  0  0  0  0999 V2000
   -2.4946   -1.7334   -0.4113 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2097   -0.4409    0.1488 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.0658    0.2596   -0.5334 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2238   -0.5088   -0.4566 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.6058   -0.7080    0.9722 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1338   -0.8083    1.0564 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6501    0.5781    0.7207 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.0075    0.7021    0.9986 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3306    0.8304   -0.7330 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.2408    1.6246   -1.0563 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2383    0.1578   -1.3061 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.4280    0.3957   -0.0085 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4815   -0.0405   -0.5523 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4878    1.7232    0.4359 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8197   -1.6503   -1.4184 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3208   -2.1165    0.1006 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0146   -0.5751    1.2309 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9100    1.2334   -0.0438 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3469    0.4614   -1.5835 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0151   -1.5226   -0.8872 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3447    0.2179    1.5313 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1222   -1.5702    1.4473 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5108   -1.5445    0.3115 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4550   -1.1480    2.0531 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0657    1.2849    1.3708 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3618    1.4848    0.5040 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2328    1.0437   -1.3402 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2160   -0.0838   -2.3879 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1754    2.4534   -0.1637 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  7  9  1  0
  9 10  1  0
 10 11  1  0
  2 12  1  0
 12 14  1  0
 12 13  2  0
 11  4  1  0
 11  9  1  0
  1 15  1  0
  1 16  1  0
  2 17  1  1
  3 18  1  0
  3 19  1  0
  4 20  1  6
  5 21  1  0
  5 22  1  0
  6 23  1  0
  6 24  1  0
  7 25  1  1
  8 26  1  0
  9 27  1  6
 11 28  1  6
 14 29  1  0
M  END


  Mrv1652307082021182D          

 14 15  0  0  1  0            999 V2000
   -0.3547    1.2396    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.3547    0.4146    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.3596    0.0021    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.0741    0.4146    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0741    1.2396    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3596    1.6521    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.3596    2.4770    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0692    0.8271    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3596   -0.8227    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3646   -1.2410    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.0741   -0.8314    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3645   -2.0603    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3573   -2.4770    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0716   -2.4687    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
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  1  6  1  0  0  0  0
  6  7  1  6  0  0  0
  1  8  1  1  0  0  0
  2  8  1  1  0  0  0
  3  9  1  1  0  0  0
  9 10  1  0  0  0  0
 10 11  1  1  0  0  0
 10 12  1  0  0  0  0
 12 13  2  0  0  0  0
 12 14  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0287060

> <DATABASE_NAME>
NP-MRD

> <SMILES>
N[C@@H](C[C@@H]1CC[C@@H](O)[C@@H]2O[C@H]12)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C9H15NO4/c10-5(9(12)13)3-4-1-2-6(11)8-7(4)14-8/h4-8,11H,1-3,10H2,(H,12,13)/t4-,5-,6+,7+,8-/m0/s1

> <INCHI_KEY>
YMLXTGCTHGQQKS-TXXZRHAASA-N

> <FORMULA>
C9H15NO4

> <MOLECULAR_WEIGHT>
201.222

> <EXACT_MASS>
201.100107967

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
29

> <JCHEM_AVERAGE_POLARIZABILITY>
19.94339983934325

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S)-2-amino-3-[(1R,2S,5R,6S)-5-hydroxy-7-oxabicyclo[4.1.0]heptan-2-yl]propanoic acid

> <ALOGPS_LOGP>
-2.65

> <JCHEM_LOGP>
-3.01395337535242

> <ALOGPS_LOGS>
-0.17

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.11548678615685

> <JCHEM_PKA_STRONGEST_ACIDIC>
2.1123553970690416

> <JCHEM_PKA_STRONGEST_BASIC>
9.515470141631313

> <JCHEM_POLAR_SURFACE_AREA>
92.78000000000002

> <JCHEM_REFRACTIVITY>
46.9771

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.37e+02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2S)-2-amino-3-[(1R,2S,5R,6S)-5-hydroxy-7-oxabicyclo[4.1.0]heptan-2-yl]propanoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 08-JUL-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   08-JUL-20         0                                  
HETATM    1  C   UNK     0      -0.662   2.314   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -0.662   0.774   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.671   0.004   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.005   0.774   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.005   2.314   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.671   3.084   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       0.671   4.624   0.000  0.00  0.00           O+0
HETATM    8  O   UNK     0      -1.996   1.544   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       0.671  -1.536   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -0.681  -2.317   0.000  0.00  0.00           C+0
HETATM   11  N   UNK     0      -2.005  -1.552   0.000  0.00  0.00           N+0
HETATM   12  C   UNK     0      -0.680  -3.846   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       0.667  -4.624   0.000  0.00  0.00           O+0
HETATM   14  O   UNK     0      -2.000  -4.608   0.000  0.00  0.00           O+0
CONECT    1    2    6    8                                                  
CONECT    2    1    3    8                                                  
CONECT    3    2    4    9                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    1    7                                                  
CONECT    7    6                                                            
CONECT    8    1    2                                                       
CONECT    9    3   10                                                       
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12                                                            
MASTER        0    0    0    0    0    0    0    0   14    0   30    0
END

View in JSmol

Synonyms

Value	Source
(1R,2S,5R,6S)-Dihydroanticapsin zwitterion	ChEBI
L-Dihydroanticapsin	ChEBI

Chemical Formula

C₉H₁₅NO₄

Average Mass

201.2220 Da

Monoisotopic Mass

201.10011 Da

IUPAC Name

(2S)-2-amino-3-[(1R,2S,5R,6S)-5-hydroxy-7-oxabicyclo[4.1.0]heptan-2-yl]propanoic acid

Traditional Name

(2S)-2-amino-3-[(1R,2S,5R,6S)-5-hydroxy-7-oxabicyclo[4.1.0]heptan-2-yl]propanoic acid

CAS Registry Number

Not Available

SMILES

N[C@@H](C[C@@H]1CC[C@@H](O)[C@@H]2O[C@H]12)C(O)=O

InChI Identifier

InChI=1S/C9H15NO4/c10-5(9(12)13)3-4-1-2-6(11)8-7(4)14-8/h4-8,11H,1-3,10H2,(H,12,13)/t4-,5-,6+,7+,8-/m0/s1

InChI Key

YMLXTGCTHGQQKS-TXXZRHAASA-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
Apis cerana	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as l-alpha-amino acids. These are alpha amino acids which have the L-configuration of the alpha-carbon atom.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

L-alpha-amino acids

Alternative Parents

Substituents

L-alpha-amino acid
Carbocyclic fatty acid
Hydroxy fatty acid
Oxepane
Fatty acyl
Cyclic alcohol
Amino acid
Carboxylic acid salt
Secondary alcohol
Oxacycle
Carboxylic acid
Dialkyl ether
Oxirane
Ether
Monocarboxylic acid or derivatives
Organoheterocyclic compound
Organonitrogen compound
Hydrocarbon derivative
Primary aliphatic amine
Organic oxygen compound
Carbonyl group
Organic nitrogen compound
Amine
Alcohol
Organooxygen compound
Organopnictogen compound
Primary amine
Organic oxide
Organic zwitterion
Organic salt
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

secondary alcohol (CHEBI:85360 )
epoxide (CHEBI:85360 )
non-proteinogenic L-alpha-amino acid (CHEBI:85360 )
oxabicycloalkane (CHEBI:85360 )
L-alanine derivative (CHEBI:85360 )

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	-2.6	ALOGPS
logP	-3	ChemAxon
logS	-0.17	ALOGPS
pKa (Strongest Acidic)	2.11	ChemAxon
pKa (Strongest Basic)	9.52	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	92.78 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	46.98 m³·mol⁻¹	ChemAxon
Polarizability	19.94 Å³	ChemAxon
Number of Rings	2	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

Not Available

Chemspider ID

34999432

KEGG Compound ID

Not Available

BioCyc ID

CPD-17531

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

86583395

PDB ID

Not Available

ChEBI ID

84358

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for l-dihydroanticapsin (NP0287060)

MOL for NP0287060 (l-dihydroanticapsin)

3D MOL for NP0287060 (l-dihydroanticapsin)

3D SDF for NP0287060 (l-dihydroanticapsin)

3D-SDF for NP0287060 (l-dihydroanticapsin)

PDB for NP0287060 (l-dihydroanticapsin)

3D PDB for NP0287060 (l-dihydroanticapsin)

SMILES for NP0287060 (l-dihydroanticapsin)

INCHI for NP0287060 (l-dihydroanticapsin)

Structure for NP0287060 (l-dihydroanticapsin)

3D Structure for NP0287060 (l-dihydroanticapsin)