NP-MRD: Showing NP-Card for (-)-Pantopyranoid C (NP0082867)

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Record Information

Version

2.0

Created at

2022-04-29 03:56:44 UTC

Updated at

2022-04-29 03:56:45 UTC

NP-MRD ID

NP0082867

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(-)-Pantopyranoid C

Description

3-Methyl-4alpha-bromo-6beta-[(1R,2E)-1-methyl-1-hydroxy-3-chloroallyl]tetrahydro-2H-pyran-3beta-ol belongs to the class of organic compounds known as oxanes. Oxanes are compounds containing an oxane (tetrahydropyran) ring, which is a six-member saturated aliphatic heterocycle with one oxygen atom and five carbon atoms. (-)-Pantopyranoid C is found in Pantoneura plocamioides. Based on a literature review very few articles have been published on 3-Methyl-4alpha-bromo-6beta-[(1R,2E)-1-methyl-1-hydroxy-3-chloroallyl]tetrahydro-2H-pyran-3beta-ol.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 31 31  0  0  0  0  0  0  0  0999 V2000
   -2.1805   -1.0699    0.7654 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9202   -0.2481   -0.4624 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.2000   -0.9706   -1.6183 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6278    1.0306   -0.5030 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8081    1.1971    0.0979 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6638    2.7275    0.0542 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -0.4227    0.0721   -0.4695 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.4215   -1.1480   -0.6106 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6052   -1.1439    0.3380 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.9251   -2.3874   -0.3701 Br  0  0  0  0  0  0  0  0  0  0  0  0
    2.1938    0.2186    0.5267 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.3155    0.5086   -0.4463 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7491    0.2772    1.8178 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1948    1.3329    0.4180 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0707    0.7989    0.6666 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6222   -0.5194    1.5987 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2308   -1.5273    1.1652 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8433   -1.9290    0.5253 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7086   -0.5325   -2.3595 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1816    1.8760   -1.0389 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1951    0.3235    0.6104 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1881    0.7460   -1.3448 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8658   -1.2254   -1.6434 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1249   -2.0888   -0.4545 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2540   -1.5403    1.3262 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9040    0.4287   -1.4681 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2045   -0.1060   -0.2855 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5830    1.5909   -0.3005 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1444   -0.5912    2.0767 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4235    2.1868    1.0830 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2042    1.7122   -0.6350 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  6
  2  4  1  0
  4  5  2  0
  5  6  1  0
  2  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
  9 11  1  0
 11 12  1  0
 11 13  1  1
 11 14  1  0
 14 15  1  0
 15  7  1  0
  1 16  1  0
  1 17  1  0
  1 18  1  0
  3 19  1  0
  4 20  1  0
  5 21  1  0
  7 22  1  6
  8 23  1  0
  8 24  1  0
  9 25  1  1
 12 26  1  0
 12 27  1  0
 12 28  1  0
 13 29  1  0
 14 30  1  0
 14 31  1  0
M  END


  Mrv1652304292205562D          

 15 15  0  0  1  0            999 V2000
    0.7145    1.2375    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4289   -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  2  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7145   -2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000   -3.3000    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    1.5395   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1105   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    1.2375    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
    1.1018    1.9659    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3272    1.9659    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
  4  7  1  1  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
  7 11  1  1  0  0  0
  7 12  1  1  0  0  0
  2 13  1  6  0  0  0
  1 14  1  6  0  0  0
  1 15  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0082867

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@@](O)(\C=C\Cl)[C@@H]1C[C@@H](Br)[C@](C)(O)CO1

> <INCHI_IDENTIFIER>
InChI=1S/C10H16BrClO3/c1-9(13,3-4-12)8-5-7(11)10(2,14)6-15-8/h3-4,7-8,13-14H,5-6H2,1-2H3/b4-3+/t7-,8+,9-,10-/m1/s1

> <INCHI_KEY>
CXSUPLDYPUBCTI-YEBTWRFZSA-N

> <FORMULA>
C10H16BrClO3

> <MOLECULAR_WEIGHT>
299.59

> <EXACT_MASS>
297.997135

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
31

> <JCHEM_AVERAGE_POLARIZABILITY>
25.400234820254816

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(3R,4R,6S)-4-bromo-6-[(2R,3E)-4-chloro-2-hydroxybut-3-en-2-yl]-3-methyloxan-3-ol

> <ALOGPS_LOGP>
1.93

> <JCHEM_LOGP>
1.3314342803333339

> <ALOGPS_LOGS>
-2.60

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.791588338645752

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.136659633696752

> <JCHEM_PKA_STRONGEST_BASIC>
-3.4040274871441216

> <JCHEM_POLAR_SURFACE_AREA>
49.69

> <JCHEM_REFRACTIVITY>
62.7418

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
7.60e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(3R,4R,6S)-4-bromo-6-[(2R,3E)-4-chloro-2-hydroxybut-3-en-2-yl]-3-methyloxan-3-ol

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 29-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   29-APR-22         0                                  
HETATM    1  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.667  -0.000   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.334  -3.850   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -0.000  -4.620   0.000  0.00  0.00           C+0
HETATM   10 Cl   UNK     0      -0.000  -6.160   0.000  0.00  0.00          Cl+0
HETATM   11  O   UNK     0       2.874  -2.310   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0      -0.206  -2.310   0.000  0.00  0.00           C+0
HETATM   13 Br   UNK     0       4.001   2.310   0.000  0.00  0.00          Br+0
HETATM   14  C   UNK     0       2.057   3.670   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       0.611   3.670   0.000  0.00  0.00           O+0
CONECT    1    2    6   14   15                                             
CONECT    2    1    3   13                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5    7                                                  
CONECT    5    4    6                                                       
CONECT    6    5    1                                                       
CONECT    7    4    8   11   12                                             
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9                                                            
CONECT   11    7                                                            
CONECT   12    7                                                            
CONECT   13    2                                                            
CONECT   14    1                                                            
CONECT   15    1                                                            
MASTER        0    0    0    0    0    0    0    0   15    0   30    0
END

View in JSmol

Synonyms

Value	Source
3-Methyl-4a-bromo-6b-[(1R,2E)-1-methyl-1-hydroxy-3-chloroallyl]tetrahydro-2H-pyran-3b-ol	Generator
3-Methyl-4α-bromo-6β-[(1R,2E)-1-methyl-1-hydroxy-3-chloroallyl]tetrahydro-2H-pyran-3β-ol	Generator

Chemical Formula

C₁₀H₁₆BrClO₃

Average Mass

299.5900 Da

Monoisotopic Mass

297.99714 Da

IUPAC Name

(3R,4R,6S)-4-bromo-6-[(2R,3E)-4-chloro-2-hydroxybut-3-en-2-yl]-3-methyloxan-3-ol

Traditional Name

(3R,4R,6S)-4-bromo-6-[(2R,3E)-4-chloro-2-hydroxybut-3-en-2-yl]-3-methyloxan-3-ol

CAS Registry Number

Not Available

SMILES

C[C@@](O)(\C=C\Cl)[C@@H]1C[C@@H](Br)[C@](C)(O)CO1

InChI Identifier

InChI=1S/C10H16BrClO3/c1-9(13,3-4-12)8-5-7(11)10(2,14)6-15-8/h3-4,7-8,13-14H,5-6H2,1-2H3/b4-3+/t7-,8+,9-,10-/m1/s1

InChI Key

CXSUPLDYPUBCTI-YEBTWRFZSA-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, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, 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
Pantoneura plocamioides	--	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as oxanes. Oxanes are compounds containing an oxane (tetrahydropyran) ring, which is a six-member saturated aliphatic heterocycle with one oxygen atom and five carbon atoms.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Oxanes

Sub Class

Not Available

Direct Parent

Oxanes

Alternative Parents

Substituents

Oxane
Tertiary alcohol
Bromohydrin
Halohydrin
Dialkyl ether
Ether
Oxacycle
Chloroalkene
Vinyl chloride
Vinyl halide
Haloalkene
Organobromide
Organohalogen compound
Hydrocarbon derivative
Organochloride
Organooxygen compound
Alkyl bromide
Alkyl halide
Organic oxygen compound
Alcohol
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic 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	1.93	ALOGPS
logP	1.33	ChemAxon
logS	-2.6	ALOGPS
pKa (Strongest Acidic)	13.14	ChemAxon
pKa (Strongest Basic)	-3.4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	49.69 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	62.74 m³·mol⁻¹	ChemAxon
Polarizability	25.4 Å³	ChemAxon
Number of Rings	1	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

10229233

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

21600017

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for (-)-Pantopyranoid C (NP0082867)

MOL for NP0082867 ((-)-Pantopyranoid C)

3D MOL for NP0082867 ((-)-Pantopyranoid C)

3D SDF for NP0082867 ((-)-Pantopyranoid C)

3D-SDF for NP0082867 ((-)-Pantopyranoid C)

PDB for NP0082867 ((-)-Pantopyranoid C)

3D PDB for NP0082867 ((-)-Pantopyranoid C)

SMILES for NP0082867 ((-)-Pantopyranoid C)

INCHI for NP0082867 ((-)-Pantopyranoid C)

Structure for NP0082867 ((-)-Pantopyranoid C)

3D Structure for NP0082867 ((-)-Pantopyranoid C)