NP-MRD: Showing NP-Card for Rugosal (NP0051822)

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Record Information

Version

2.0

Created at

2022-04-27 23:02:35 UTC

Updated at

2022-04-27 23:02:35 UTC

NP-MRD ID

NP0051822

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Rugosal

Description

Rugosal belongs to the class of organic compounds known as 1,2-dioxanes. These are organic compounds containing 1,2-dioxane, an aliphatic six-member ring with two oxygen atoms in ring positions 1 and 2. Rugosal is found in Rosa rugosa . Rugosal was first documented in 1984 (PMID: 6387349). Based on a literature review a small amount of articles have been published on Rugosal (PMID: 8652154) (PMID: 7488516) (PMID: 2874819).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 41 43  0  0  0  0  0  0  0  0999 V2000
   -3.8178   -0.2611    0.1095 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5001    0.5141   -0.0475 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.6072    1.6713    0.8866 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3910   -0.4277    0.2930 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.3453   -1.6427   -0.5735 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0822   -2.3207   -0.0195 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8654   -1.1095   -0.0680 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.3914   -1.1492   -1.5058 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0601   -1.2808    0.7989 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4125    0.0964    1.3742 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.2768    0.4293    2.1059 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2483    0.6949    1.4458 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0030    0.0841    0.2322 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.3183    1.1094   -0.8169 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.4759    2.2162   -0.8630 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6939    1.6247   -0.4638 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6064    1.1079    0.3330 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9450    1.6109    0.1408 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8691    1.1649    0.8642 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6343    0.4125    0.4526 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1520   -0.6845   -0.8574 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7380   -1.0607    0.8464 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4531    0.7736   -1.1210 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4662    1.5590    1.6190 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7531    1.8753    1.5281 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9400    2.5658    0.2798 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5858   -0.7886    1.3338 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1517   -2.3716   -0.3880 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3007   -1.4141   -1.6273 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2610   -3.1323   -0.6643 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2970   -2.5963    1.0156 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1630   -0.4162   -1.7199 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6160   -1.2622   -2.2602 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9432   -2.1431   -1.5345 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8637   -1.9322    1.6877 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9378   -1.6975    0.2796 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2692    0.0033    2.0552 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4003    0.7087   -1.8400 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5903    2.5653   -1.7676 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9287    2.5515   -0.9553 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2140    2.3518   -0.5885 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  6
  7  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 13 12  1  1
 13 14  1  0
 14 15  1  0
 14 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 13  4  1  0
 13  7  1  0
 17 10  1  0
  1 20  1  0
  1 21  1  0
  1 22  1  0
  2 23  1  6
  3 24  1  0
  3 25  1  0
  3 26  1  0
  4 27  1  1
  5 28  1  0
  5 29  1  0
  6 30  1  0
  6 31  1  0
  8 32  1  0
  8 33  1  0
  8 34  1  0
  9 35  1  0
  9 36  1  0
 10 37  1  1
 14 38  1  6
 15 39  1  0
 16 40  1  0
 18 41  1  0
M  END


  Mrv1652304282201022D          

 19 21  0  0  1  0            999 V2000
    1.8224   -0.0773    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.9316   -0.9795    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.6909   -1.4949    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.5063   -1.1193    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7295   -0.2565    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3254    0.5440    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.4233    0.5958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8269   -0.0388    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7078   -0.8024    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5497   -0.1682    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8834    0.5863    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6230   -2.3171    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1256   -1.2631    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.5235   -0.6756    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9715    0.0330    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9477   -2.0686    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5564   -2.6255    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1611   -2.3173    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6095   -0.3244    0.0000 C   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  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  1  7  1  0  0  0  0
  6  8  1  6  0  0  0
  8  9  1  0  0  0  0
  2  9  1  6  0  0  0
  5 10  1  0  0  0  0
 10 11  2  0  0  0  0
  3 12  1  6  0  0  0
  2 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
  1 15  1  0  0  0  0
 13 16  1  1  0  0  0
 16 17  1  0  0  0  0
 16 18  1  0  0  0  0
  1 19  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0051822

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)[C@H]1CC[C@]2(C)C[C@@H]3OO[C@]12[C@@H](O)C=C3C=O

> <INCHI_IDENTIFIER>
InChI=1S/C15H22O4/c1-9(2)11-4-5-14(3)7-12-10(8-16)6-13(17)15(11,14)19-18-12/h6,8-9,11-13,17H,4-5,7H2,1-3H3/t11-,12+,13+,14-,15+/m1/s1

> <INCHI_KEY>
NTVXLOKDTRVPSZ-FQKPHLNHSA-N

> <FORMULA>
C15H22O4

> <MOLECULAR_WEIGHT>
266.337

> <EXACT_MASS>
266.151809188

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
41

> <JCHEM_AVERAGE_POLARIZABILITY>
28.371899900256935

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1R,2R,5R,7S,10S)-10-hydroxy-5-methyl-2-(propan-2-yl)-11,12-dioxatricyclo[5.3.2.0^{1,5}]dodec-8-ene-8-carbaldehyde

> <ALOGPS_LOGP>
1.91

> <JCHEM_LOGP>
2.0147514689999997

> <ALOGPS_LOGS>
-2.32

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.420559633884796

> <JCHEM_PKA_STRONGEST_BASIC>
-3.48964721613879

> <JCHEM_POLAR_SURFACE_AREA>
55.760000000000005

> <JCHEM_REFRACTIVITY>
70.212

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.27e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1R,2R,5R,7S,10S)-10-hydroxy-2-isopropyl-5-methyl-11,12-dioxatricyclo[5.3.2.0^{1,5}]dodec-8-ene-8-carbaldehyde

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 28-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   28-APR-22         0                                  
HETATM    1  C   UNK     0       3.402  -0.144   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       3.606  -1.828   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       5.023  -2.790   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       6.545  -2.089   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       6.962  -0.479   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       6.207   1.015   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.523   1.112   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       5.277  -0.072   0.000  0.00  0.00           O+0
HETATM    9  O   UNK     0       5.055  -1.498   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       8.493  -0.314   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       9.116   1.095   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0       4.896  -4.325   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       2.101  -2.358   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       0.977  -1.261   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       1.814   0.062   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       1.769  -3.861   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       2.905  -4.901   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       0.301  -4.326   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       4.871  -0.606   0.000  0.00  0.00           C+0
CONECT    1    2    7   15   19                                             
CONECT    2    1    3    9   13                                             
CONECT    3    2    4   12                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6   10                                                  
CONECT    6    5    7    8                                                  
CONECT    7    6    1                                                       
CONECT    8    6    9                                                       
CONECT    9    8    2                                                       
CONECT   10    5   11                                                       
CONECT   11   10                                                            
CONECT   12    3                                                            
CONECT   13    2   14   16                                                  
CONECT   14   13   15                                                       
CONECT   15   14    1                                                       
CONECT   16   13   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16                                                            
CONECT   19    1                                                            
MASTER        0    0    0    0    0    0    0    0   19    0   42    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₅H₂₂O₄

Average Mass

266.3370 Da

Monoisotopic Mass

266.15181 Da

IUPAC Name

(1R,2R,5R,7S,10S)-10-hydroxy-5-methyl-2-(propan-2-yl)-11,12-dioxatricyclo[5.3.2.0^{1,5}]dodec-8-ene-8-carbaldehyde

Traditional Name

(1R,2R,5R,7S,10S)-10-hydroxy-2-isopropyl-5-methyl-11,12-dioxatricyclo[5.3.2.0^{1,5}]dodec-8-ene-8-carbaldehyde

CAS Registry Number

Not Available

SMILES

CC(C)[C@H]1CC[C@]2(C)C[C@@H]3OO[C@]12[C@@H](O)C=C3C=O

InChI Identifier

InChI=1S/C15H22O4/c1-9(2)11-4-5-14(3)7-12-10(8-16)6-13(17)15(11,14)19-18-12/h6,8-9,11-13,17H,4-5,7H2,1-3H3/t11-,12+,13+,14-,15+/m1/s1

InChI Key

NTVXLOKDTRVPSZ-FQKPHLNHSA-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
Rosa rugosa	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 1,2-dioxanes. These are organic compounds containing 1,2-dioxane, an aliphatic six-member ring with two oxygen atoms in ring positions 1 and 2.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Dioxanes

Sub Class

1,2-dioxanes

Direct Parent

1,2-dioxanes

Alternative Parents

Substituents

Ortho-dioxane
Dialkyl peroxide
Secondary alcohol
Oxacycle
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aldehyde
Alcohol
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

dioxanes (CHEBI:8910 )
Sesquiterpenoids (C15) (C09717 )

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	1.91	ALOGPS
logP	2.01	ChemAxon
logS	-2.3	ALOGPS
pKa (Strongest Acidic)	13.42	ChemAxon
pKa (Strongest Basic)	-3.5	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	55.76 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	70.21 m³·mol⁻¹	ChemAxon
Polarizability	28.37 Å³	ChemAxon
Number of Rings	3	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

C00003180

Chemspider ID

390836

KEGG Compound ID

C09717

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

442391

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Meyer zum Gottesberge AM, Mai JK: Time-dependent alterations of 3-fucosyl-N-acetyl-lactosamine (CD15) expression in the endolymphatic sac of adult guinea pigs after glycerol administration. Eur Arch Otorhinolaryngol. 1996;253(3):136-41. doi: 10.1007/BF00615110. [PubMed:8652154 ]
Meyer zum Gottesberge AM, Mai JK: Expression of the carbohydrate epitope 3-fucosyl-N-acetyl-lactosamine (CD 15) in the adult guinea pig inner ear. Eur J Morphol. 1995 Apr;33(2):129-35. [PubMed:7488516 ]
Arnold W, Altermatt HJ, Arnold R, Gebbers JO, Laissue J: Somatostatin (somatostatinlike) immunoreactive cells in the human inner ear. Arch Otolaryngol Head Neck Surg. 1986 Sep;112(9):934-7. doi: 10.1001/archotol.1986.03780090030004. [PubMed:2874819 ]
Arnold W, Altermatt HJ, Gebbers JO: [Qualitative detection of immunoglobulins in the human endolymphatic sac]. Laryngol Rhinol Otol (Stuttg). 1984 Sep;63(9):464-7. [PubMed:6387349 ]

Showing NP-Card for Rugosal (NP0051822)

MOL for NP0051822 (Rugosal)

3D MOL for NP0051822 (Rugosal)

3D SDF for NP0051822 (Rugosal)

3D-SDF for NP0051822 (Rugosal)

PDB for NP0051822 (Rugosal)

3D PDB for NP0051822 (Rugosal)

SMILES for NP0051822 (Rugosal)

INCHI for NP0051822 (Rugosal)

Structure for NP0051822 (Rugosal)

3D Structure for NP0051822 (Rugosal)