NP-MRD: Showing NP-Card for n-[(1r,2s,3s,4r,5r,6s)-3-carbamimidamido-2,4,5,6-tetrahydroxycyclohexyl]guanidine (NP0239530)

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Record Information

Version

2.0

Created at

2022-09-06 23:09:14 UTC

Updated at

2022-09-06 23:09:15 UTC

NP-MRD ID

NP0239530

Secondary Accession Numbers

None

Natural Product Identification

Common Name

n-[(1r,2s,3s,4r,5r,6s)-3-carbamimidamido-2,4,5,6-tetrahydroxycyclohexyl]guanidine

Description

n-[(1r,2s,3s,4r,5r,6s)-3-carbamimidamido-2,4,5,6-tetrahydroxycyclohexyl]guanidine is found in Apis cerana.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 36 36  0  0  0  0  0  0  0  0999 V2000
    5.0966    1.7659   -1.1231 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0597    1.8636   -1.1693 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.3570    1.2825   -0.2436 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9707    0.5367    0.8010 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.9388    1.3903   -0.2688 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.0770    0.3234    0.2283 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.3425    0.7912    0.2599 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.4738    1.8864    1.0813 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1749   -0.3993    0.7540 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.4936   -0.0009    1.1316 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4097    0.6387    0.2849 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1937    1.7431    0.7254 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5751    0.2451   -0.9324 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2393    0.6880   -1.5895 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1540   -1.3848   -0.3911 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.9807   -2.4951   -0.1207 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2198   -1.8914   -0.6197 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.2440   -2.4786   -1.9067 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3176   -0.9185   -0.5305 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.4285   -1.5711    0.0575 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5386    0.4577    1.7514 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8855    0.0571    0.5934 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5328    2.2687   -0.6594 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3903    0.1679    1.3016 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6735    0.9986   -0.7871 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2377    2.6952    0.5273 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6151   -0.8309    1.5891 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8053   -0.2024    2.1246 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8416    1.5713    1.5153 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1568    2.6826    0.3153 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4917   -0.8433   -1.3056 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3733   -2.7569   -0.9924 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3821   -2.7612    0.0814 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9781   -3.1319   -1.9279 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6835   -0.6333   -1.5602 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1315   -1.7544    1.0047 H   0  0  0  0  0  0  0  0  0  0  0  0
 12 11  1  0
 11 13  2  0
 11 10  1  0
 10  9  1  0
  9 15  1  0
 15 16  1  0
 15 17  1  0
 17 18  1  0
 17 19  1  0
 19 20  1  0
 19  6  1  0
  6  5  1  0
  5  3  1  0
  3  4  1  0
  3  2  2  0
  6  7  1  0
  7  8  1  0
  7  9  1  0
 12 29  1  0
 12 30  1  0
 13 14  1  0
 10 28  1  0
  9 27  1  1
 15 31  1  6
 16 32  1  0
 17 33  1  1
 18 34  1  0
 19 35  1  6
 20 36  1  0
  6 24  1  1
  5 23  1  0
  4 21  1  0
  4 22  1  0
  2  1  1  0
  7 25  1  6
  8 26  1  0
M  END

 
  Mrv1533006081517212D          
 
 18 18  0  0  1  0            999 V2000
   17.2610  -12.5047    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   17.2610  -11.6841    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   17.9756  -12.9168    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   16.4075  -13.0221    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   17.9756  -11.2681    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   16.5464  -11.2255    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.6904  -12.5047    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   17.9795  -13.7800    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.2844  -12.5343    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.6904  -11.6841    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   17.9756  -10.4049    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   19.4790  -12.9595    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.2844  -11.7137    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.5698  -12.9466    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   19.3937  -11.2681    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.6904   -9.9965    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.4012  -10.4049    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   18.6904   -9.1722    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  3  1  0  0  0  0
  1  4  1  1  0  0  0
  2  5  1  0  0  0  0
  2  6  1  6  0  0  0
  3  7  1  0  0  0  0
  3  8  1  6  0  0  0
  4  9  1  0  0  0  0
  5 10  1  0  0  0  0
  5 11  1  1  0  0  0
  7 12  1  1  0  0  0
  9 13  2  0  0  0  0
  9 14  1  0  0  0  0
 10 15  1  6  0  0  0
 11 16  1  0  0  0  0
 16 17  1  0  0  0  0
 16 18  2  0  0  0  0
  7 10  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0239530

> <DATABASE_NAME>
NP-MRD

> <SMILES>
NC(=N)N[C@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](NC(N)=N)[C@@H]1O

> <INCHI_IDENTIFIER>
InChI=1S/C8H18N6O4/c9-7(10)13-1-3(15)2(14-8(11)12)5(17)6(18)4(1)16/h1-6,15-18H,(H4,9,10,13)(H4,11,12,14)/t1-,2+,3-,4+,5-,6-

> <INCHI_KEY>
MSXMXWJPFIDEMT-FAEUDGQSSA-N

> <FORMULA>
C8H18N6O4

> <MOLECULAR_WEIGHT>
262.27

> <EXACT_MASS>
262.138953084

> <JCHEM_ACCEPTOR_COUNT>
10

> <JCHEM_ATOM_COUNT>
36

> <JCHEM_AVERAGE_POLARIZABILITY>
24.96104494886966

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
10

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
N-[(1R,2s,3S,4R,5r,6S)-3-carbamimidamido-2,4,5,6-tetrahydroxycyclohexyl]guanidine

> <ALOGPS_LOGP>
-3.22

> <JCHEM_LOGP>
-4.845562451196927

> <ALOGPS_LOGS>
-1.75

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
2

> <JCHEM_PKA>
14.43141487401433

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.970313279384182

> <JCHEM_PKA_STRONGEST_BASIC>
11.52514656747692

> <JCHEM_POLAR_SURFACE_AREA>
204.72

> <JCHEM_REFRACTIVITY>
80.5192

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
4.70e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
N-[(1R,2s,3S,4R,5r,6S)-3-carbamimidamido-2,4,5,6-tetrahydroxycyclohexyl]guanidine

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 08-JUN-15   NONE
TITLE     NULL                                                        
COMPND    MOLECULE:                                                   
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   08-JUN-15         0                                  
HETATM    1  C   UNK     0      32.220 -23.342   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      32.220 -21.810   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      33.555 -24.111   0.000  0.00  0.00           C+0
HETATM    4  N   UNK     0      30.627 -24.308   0.000  0.00  0.00           N+0
HETATM    5  C   UNK     0      33.555 -21.034   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0      30.887 -20.954   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0      34.889 -23.342   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0      33.562 -25.723   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0      28.531 -23.397   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      34.889 -21.810   0.000  0.00  0.00           C+0
HETATM   11  N   UNK     0      33.555 -19.423   0.000  0.00  0.00           N+0
HETATM   12  O   UNK     0      36.361 -24.191   0.000  0.00  0.00           O+0
HETATM   13  N   UNK     0      28.531 -21.866   0.000  0.00  0.00           N+0
HETATM   14  N   UNK     0      27.197 -24.167   0.000  0.00  0.00           N+0
HETATM   15  O   UNK     0      36.202 -21.034   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0      34.889 -18.660   0.000  0.00  0.00           C+0
HETATM   17  N   UNK     0      36.216 -19.423   0.000  0.00  0.00           N+0
HETATM   18  N   UNK     0      34.889 -17.121   0.000  0.00  0.00           N+0
CONECT    1    2    3    4                                                  
CONECT    2    1    5    6                                                  
CONECT    3    1    7    8                                                  
CONECT    4    1    9                                                       
CONECT    5    2   10   11                                                  
CONECT    6    2                                                            
CONECT    7    3   12   10                                                  
CONECT    8    3                                                            
CONECT    9    4   13   14                                                  
CONECT   10    5   15    7                                                  
CONECT   11    5   16                                                       
CONECT   12    7                                                            
CONECT   13    9                                                            
CONECT   14    9                                                            
CONECT   15   10                                                            
CONECT   16   11   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16                                                            
MASTER        0    0    0    0    0    0    0    0   18    0   36    0
END

View in JSmol

Synonyms

Value	Source
1,1'-(2,4,5,6-Tetrahydroxy-1,3-cyclohexylene)diguanidine	ChEBI
1,3-diguanidino-2,4,5,6-Cyclohexanetetrol	ChEBI
N,N'-bis(aminoiminomethyl)streptamine	ChEBI
N,N'-diamidinostreptamine	ChEBI

Chemical Formula

C₈H₁₈N₆O₄

Average Mass

262.2700 Da

Monoisotopic Mass

262.13895 Da

IUPAC Name

N-[(1R,2s,3S,4R,5r,6S)-3-carbamimidamido-2,4,5,6-tetrahydroxycyclohexyl]guanidine

Traditional Name

N-[(1R,2s,3S,4R,5r,6S)-3-carbamimidamido-2,4,5,6-tetrahydroxycyclohexyl]guanidine

CAS Registry Number

Not Available

SMILES

NC(=N)N[C@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](NC(N)=N)[C@@H]1O

InChI Identifier

InChI=1S/C8H18N6O4/c9-7(10)13-1-3(15)2(14-8(11)12)5(17)6(18)4(1)16/h1-6,15-18H,(H4,9,10,13)(H4,11,12,14)/t1-,2+,3-,4+,5-,6-

InChI Key

MSXMXWJPFIDEMT-FAEUDGQSSA-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

This compound belongs to the class of organic compounds known as aminocyclitols. These are cyclitols with at least one hydroxyl group replace by an amino group.

Kingdom

Organic compounds

Super Class

Organooxygen compounds

Class

Alcohols and polyols

Sub Class

Cyclic alcohols and derivatives

Direct Parent

Aminocyclitols

Alternative Parents

Substituents

Aminocyclitol
Cyclohexanol
Secondary alcohol
Guanidine
1,2-diol
Carboximidamide
Polyol
Hydrocarbon derivative
Organonitrogen compound
Imine
Aliphatic homomonocyclic compound

Molecular Framework

Aliphatic homomonocyclic compounds

External Descriptors

guanidines (CHEBI:27405 )
amino cyclitol (CHEBI:27405 )

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	-3.2	ALOGPS
logP	-4.8	ChemAxon
logS	-1.8	ALOGPS
pKa (Strongest Acidic)	12.97	ChemAxon
pKa (Strongest Basic)	11.53	ChemAxon
Physiological Charge	2	ChemAxon
Hydrogen Acceptor Count	10	ChemAxon
Hydrogen Donor Count	10	ChemAxon
Polar Surface Area	204.72 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	80.52 m³·mol⁻¹	ChemAxon
Polarizability	24.96 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	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

16736034

KEGG Compound ID

C00837

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

27405

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for n-[(1r,2s,3s,4r,5r,6s)-3-carbamimidamido-2,4,5,6-tetrahydroxycyclohexyl]guanidine (NP0239530)

MOL for NP0239530 (n-[(1r,2s,3s,4r,5r,6s)-3-carbamimidamido-2,4,5,6-tetrahydroxycyclohexyl]guanidine)

3D MOL for NP0239530 (n-[(1r,2s,3s,4r,5r,6s)-3-carbamimidamido-2,4,5,6-tetrahydroxycyclohexyl]guanidine)

3D SDF for NP0239530 (n-[(1r,2s,3s,4r,5r,6s)-3-carbamimidamido-2,4,5,6-tetrahydroxycyclohexyl]guanidine)

3D-SDF for NP0239530 (n-[(1r,2s,3s,4r,5r,6s)-3-carbamimidamido-2,4,5,6-tetrahydroxycyclohexyl]guanidine)

PDB for NP0239530 (n-[(1r,2s,3s,4r,5r,6s)-3-carbamimidamido-2,4,5,6-tetrahydroxycyclohexyl]guanidine)

3D PDB for NP0239530 (n-[(1r,2s,3s,4r,5r,6s)-3-carbamimidamido-2,4,5,6-tetrahydroxycyclohexyl]guanidine)

SMILES for NP0239530 (n-[(1r,2s,3s,4r,5r,6s)-3-carbamimidamido-2,4,5,6-tetrahydroxycyclohexyl]guanidine)

INCHI for NP0239530 (n-[(1r,2s,3s,4r,5r,6s)-3-carbamimidamido-2,4,5,6-tetrahydroxycyclohexyl]guanidine)

Structure for NP0239530 (n-[(1r,2s,3s,4r,5r,6s)-3-carbamimidamido-2,4,5,6-tetrahydroxycyclohexyl]guanidine)

3D Structure for NP0239530 (n-[(1r,2s,3s,4r,5r,6s)-3-carbamimidamido-2,4,5,6-tetrahydroxycyclohexyl]guanidine)