NP-MRD: Showing NP-Card for (2r,3r,5r,6s)-heptane-1,2,3,4,5,6,7-heptol (NP0147646)

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Record Information

Version

2.0

Created at

2022-09-02 03:17:40 UTC

Updated at

2022-09-02 03:17:40 UTC

NP-MRD ID

NP0147646

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(2r,3r,5r,6s)-heptane-1,2,3,4,5,6,7-heptol

Description

Perseitol belongs to the class of organic compounds known as sugar alcohols. These are hydrogenated forms of carbohydrate in which the carbonyl group (aldehyde or ketone, reducing sugar) has been reduced to a primary or secondary hydroxyl group. (2r,3r,5r,6s)-heptane-1,2,3,4,5,6,7-heptol is found in Parmotrema cetratum and Persea americana. (2r,3r,5r,6s)-heptane-1,2,3,4,5,6,7-heptol was first documented in 2019 (PMID: 31293606). Based on a literature review a small amount of articles have been published on Perseitol (PMID: 33648254) (PMID: 34834789) (PMID: 33761337) (PMID: 32560627).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 30 29  0  0  0  0  0  0  0  0999 V2000
   -3.5634    0.6037   -1.3768 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6315    0.8515   -0.3597 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1633   -0.4694    0.1539 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.2949   -1.1565    0.6484 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1175   -0.3886    1.2138 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7471   -1.6778    1.5787 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0795    0.4618    0.8304 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.8949    0.5131    1.9417 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7883   -0.1771   -0.3034 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.2193   -1.4697    0.0049 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9005    0.5920   -0.9375 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.1969   -0.1455   -2.1310 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1655    0.6372   -0.1470 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0900    1.3521    1.0265 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3523    0.1881   -0.9173 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1563    1.3923    0.4576 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8419    1.4823   -0.7719 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8132   -1.0873   -0.7180 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0557   -1.7013    1.4410 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6263    0.0479    2.1224 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8835   -2.2601    0.7973 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2758    1.4769    0.5351 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0071   -0.4407    2.2504 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0104   -0.3308   -1.1260 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1854   -2.0508   -0.7957 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6031    1.5955   -1.2505 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8138   -0.8706   -1.8487 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0122    1.0958   -0.7347 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5171   -0.3942    0.0787 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0386    2.3305    0.8286 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
  3  5  1  0
  5  6  1  0
  5  7  1  0
  7  8  1  0
  7  9  1  0
  9 10  1  0
  9 11  1  0
 11 12  1  0
 11 13  1  0
 13 14  1  0
  1 15  1  0
  2 16  1  0
  2 17  1  0
  3 18  1  6
  4 19  1  0
  5 20  1  1
  6 21  1  0
  7 22  1  6
  8 23  1  0
  9 24  1  6
 10 25  1  0
 11 26  1  6
 12 27  1  0
 13 28  1  0
 13 29  1  0
 14 30  1  0
M  END


  Mrv1652309022205172D          

 14 13  0  0  1  0            999 V2000
    2.9980    2.5559    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7125    2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4270    2.5559    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.4270    3.3809    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1414    2.1434    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.1414    1.3184    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8559    2.5559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8559    3.3809    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.5704    2.1434    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.5704    1.3184    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.2849    2.5559    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    7.2849    3.3809    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.9993    2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7138    2.5559    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  6  0  0  0
  3  5  1  0  0  0  0
  5  6  1  6  0  0  0
  5  7  1  0  0  0  0
  7  8  1  0  0  0  0
  7  9  1  0  0  0  0
  9 10  1  1  0  0  0
  9 11  1  0  0  0  0
 11 12  1  6  0  0  0
 11 13  1  0  0  0  0
 13 14  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0147646

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC[C@H](O)[C@@H](O)C(O)[C@H](O)[C@H](O)CO

> <INCHI_IDENTIFIER>
InChI=1S/C7H16O7/c8-1-3(10)5(12)7(14)6(13)4(11)2-9/h3-14H,1-2H2/t3-,4+,5-,6-,7?/m1/s1

> <INCHI_KEY>
OXQKEKGBFMQTML-RYRJNEICSA-N

> <FORMULA>
C7H16O7

> <MOLECULAR_WEIGHT>
212.198

> <EXACT_MASS>
212.089602855

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
30

> <JCHEM_AVERAGE_POLARIZABILITY>
19.937783301083016

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
7

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2R,3R,5R,6S)-heptane-1,2,3,4,5,6,7-heptol

> <ALOGPS_LOGP>
-2.71

> <JCHEM_LOGP>
-4.360353790666667

> <ALOGPS_LOGS>
0.13

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.13402824100833

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.460608929313874

> <JCHEM_PKA_STRONGEST_BASIC>
-2.974211733461736

> <JCHEM_POLAR_SURFACE_AREA>
141.61

> <JCHEM_REFRACTIVITY>
44.366099999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.89e+02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2R,3R,5R,6S)-heptane-1,2,3,4,5,6,7-heptol

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 02-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   02-SEP-22         0                                  
HETATM    1  O   UNK     0       5.596   4.771   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       6.930   4.001   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       8.264   4.771   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       8.264   6.311   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       9.597   4.001   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       9.597   2.461   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0      10.931   4.771   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0      10.931   6.311   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0      12.265   4.001   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0      12.265   2.461   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0      13.598   4.771   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      13.598   6.311   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0      14.932   4.001   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0      16.266   4.771   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14                                                       
CONECT   14   13                                                            
MASTER        0    0    0    0    0    0    0    0   14    0   26    0
END

View in JSmol

Synonyms

Value	Source
D-Glycero-D-galacto-heptitol	MeSH
L-Glycero-D-mannoheptitol	MeSH
Perseitol, (L-galacto)-isomer	MeSH
Perseitol,. (L-glycero-D-galacto)-isomer	MeSH
L-Glycero-D-manno-heptitol	MeSH

Chemical Formula

C₇H₁₆O₇

Average Mass

212.1980 Da

Monoisotopic Mass

212.08960 Da

IUPAC Name

(2R,3R,5R,6S)-heptane-1,2,3,4,5,6,7-heptol

Traditional Name

(2R,3R,5R,6S)-heptane-1,2,3,4,5,6,7-heptol

CAS Registry Number

Not Available

SMILES

OC[C@H](O)[C@@H](O)C(O)[C@H](O)[C@H](O)CO

InChI Identifier

InChI=1S/C7H16O7/c8-1-3(10)5(12)7(14)6(13)4(11)2-9/h3-14H,1-2H2/t3-,4+,5-,6-,7?/m1/s1

InChI Key

OXQKEKGBFMQTML-RYRJNEICSA-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
Parmotrema cetratum	LOTUS Database	35616633
Persea americana	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as sugar alcohols. These are hydrogenated forms of carbohydrate in which the carbonyl group (aldehyde or ketone, reducing sugar) has been reduced to a primary or secondary hydroxyl group.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbohydrates and carbohydrate conjugates

Direct Parent

Sugar alcohols

Alternative Parents

Substituents

Sugar alcohol
Monosaccharide
Secondary alcohol
Polyol
Hydrocarbon derivative
Primary alcohol
Alcohol
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic 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	-2.7	ALOGPS
logP	-4.4	ChemAxon
logS	0.13	ALOGPS
pKa (Strongest Acidic)	12.46	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	7	ChemAxon
Polar Surface Area	141.61 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	44.37 m³·mol⁻¹	ChemAxon
Polarizability	19.94 Å³	ChemAxon
Number of Rings	0	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

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00001167

Chemspider ID

390169

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

441436

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Ramos-Aguilar AL, Ornelas-Paz J, Tapia-Vargas LM, Gardea-Bejar AA, Yahia EM, Ornelas-Paz JJ, Ruiz-Cruz S, Rios-Velasco C, Escalante-Minakata P: Effect of cultivar on the content of selected phytochemicals in avocado peels. Food Res Int. 2021 Feb;140:110024. doi: 10.1016/j.foodres.2020.110024. Epub 2020 Dec 17. [PubMed:33648254 ]
Pedreschi R, Uarrota V, Fuentealba C, Alvaro JE, Olmedo P, Defilippi BG, Meneses C, Campos-Vargas R: Primary Metabolism in Avocado Fruit. Front Plant Sci. 2019 Jun 26;10:795. doi: 10.3389/fpls.2019.00795. eCollection 2019. [PubMed:31293606 ]
Chirinos R, Campos D, Martinez S, Llanos S, Betalleluz-Pallardel I, Garcia-Rios D, Pedreschi R: The Effect of Hydrothermal Treatment on Metabolite Composition of Hass Avocados Stored in a Controlled Atmosphere. Plants (Basel). 2021 Nov 10;10(11):2427. doi: 10.3390/plants10112427. [PubMed:34834789 ]
Ramos-Aguilar AL, Ornelas-Paz J, Tapia-Vargas LM, Gardea-Bejar AA, Yahia EM, Ornelas-Paz JJ, Perez-Martinez JD, Rios-Velasco C, Escalante-Minakata P: Metabolomic analysis and physical attributes of ripe fruits from Mexican Creole (Persea americana var. Drymifolia) and 'Hass' avocados. Food Chem. 2021 Aug 30;354:129571. doi: 10.1016/j.foodchem.2021.129571. Epub 2021 Mar 13. [PubMed:33761337 ]
Vazquez-Manjarrez N, Ulaszewska M, Garcia-Aloy M, Mattivi F, Pratico G, Dragsted LO, Manach C: Biomarkers of intake for tropical fruits. Genes Nutr. 2020 Jun 19;15(1):11. doi: 10.1186/s12263-020-00670-4. [PubMed:32560627 ]
LOTUS database [Link]

Showing NP-Card for (2r,3r,5r,6s)-heptane-1,2,3,4,5,6,7-heptol (NP0147646)

MOL for NP0147646 ((2r,3r,5r,6s)-heptane-1,2,3,4,5,6,7-heptol)

3D MOL for NP0147646 ((2r,3r,5r,6s)-heptane-1,2,3,4,5,6,7-heptol)

3D SDF for NP0147646 ((2r,3r,5r,6s)-heptane-1,2,3,4,5,6,7-heptol)

3D-SDF for NP0147646 ((2r,3r,5r,6s)-heptane-1,2,3,4,5,6,7-heptol)

PDB for NP0147646 ((2r,3r,5r,6s)-heptane-1,2,3,4,5,6,7-heptol)

3D PDB for NP0147646 ((2r,3r,5r,6s)-heptane-1,2,3,4,5,6,7-heptol)

SMILES for NP0147646 ((2r,3r,5r,6s)-heptane-1,2,3,4,5,6,7-heptol)

INCHI for NP0147646 ((2r,3r,5r,6s)-heptane-1,2,3,4,5,6,7-heptol)

Structure for NP0147646 ((2r,3r,5r,6s)-heptane-1,2,3,4,5,6,7-heptol)

3D Structure for NP0147646 ((2r,3r,5r,6s)-heptane-1,2,3,4,5,6,7-heptol)