NP-MRD: Showing NP-Card for 13-[5-(2-hydroxypropan-2-yl)-2-methyloxolan-2-yl]-1,5,16-trimethyl-4-(prop-1-en-2-yl)-9-oxatetracyclo[8.6.1.0⁵,¹⁷.0¹²,¹⁶]heptadecan-8-one (NP0304721)

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Record Information

Version

2.0

Created at

2022-09-10 20:01:29 UTC

Updated at

2022-09-10 20:01:30 UTC

NP-MRD ID

NP0304721

Secondary Accession Numbers

None

Natural Product Identification

Common Name

13-[5-(2-hydroxypropan-2-yl)-2-methyloxolan-2-yl]-1,5,16-trimethyl-4-(prop-1-en-2-yl)-9-oxatetracyclo[8.6.1.0⁵,¹⁷.0¹²,¹⁶]heptadecan-8-one

Description

13-[5-(2-Hydroxypropan-2-yl)-2-methyloxolan-2-yl]-1,5,16-trimethyl-4-(prop-1-en-2-yl)-9-oxatetracyclo[8.6.1.0⁵,¹⁷.0¹²,¹⁶]Heptadecan-8-one belongs to the class of organic compounds known as terpene glycosides. These are prenol lipids containing a carbohydrate moiety glycosidically bound to a terpene backbone. 13-[5-(2-hydroxypropan-2-yl)-2-methyloxolan-2-yl]-1,5,16-trimethyl-4-(prop-1-en-2-yl)-9-oxatetracyclo[8.6.1.0⁵,¹⁷.0¹²,¹⁶]heptadecan-8-one is found in Betula ovalifolia. 13-[5-(2-Hydroxypropan-2-yl)-2-methyloxolan-2-yl]-1,5,16-trimethyl-4-(prop-1-en-2-yl)-9-oxatetracyclo[8.6.1.0⁵,¹⁷.0¹²,¹⁶]Heptadecan-8-one is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004191518142D          

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M  END

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M  END


  Mrv1533004191518142D          

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   -0.6450    1.3394    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4493    1.1558    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9637    1.8008    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8073    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4493   -0.3308    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6450   -0.5144    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3139   -0.9973    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  2  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  7  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
  7 16  1  0  0  0  0
 12 16  1  0  0  0  0
 16 17  1  0  0  0  0
 13 18  1  0  0  0  0
 18 19  1  0  0  0  0
 18 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 18 23  1  0  0  0  0
 22 24  1  0  0  0  0
 24 25  1  0  0  0  0
 24 26  1  0  0  0  0
 24 27  1  0  0  0  0
 10 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  2  0  0  0  0
 29 31  1  0  0  0  0
 31 32  1  0  0  0  0
 32 33  1  0  0  0  0
  4 33  1  0  0  0  0
  9 33  1  0  0  0  0
 33 34  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0304721

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(=C)C1CCC2(C)C3C(CC4C(CCC24C)C2(C)CCC(O2)C(C)(C)O)OC(=O)CCC13C

> <INCHI_IDENTIFIER>
InChI=1S/C30H48O4/c1-18(2)19-9-15-29(7)25-22(33-24(31)12-13-27(19,25)5)17-21-20(10-14-28(21,29)6)30(8)16-11-23(34-30)26(3,4)32/h19-23,25,32H,1,9-17H2,2-8H3

> <INCHI_KEY>
SEBLWBUGZCPRKV-UHFFFAOYSA-N

> <FORMULA>
C30H48O4

> <MOLECULAR_WEIGHT>
472.71

> <EXACT_MASS>
472.355260026

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
82

> <JCHEM_AVERAGE_POLARIZABILITY>
55.40771946173642

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
13-[5-(2-hydroxypropan-2-yl)-2-methyloxolan-2-yl]-1,5,16-trimethyl-4-(prop-1-en-2-yl)-9-oxatetracyclo[8.6.1.0⁵,¹⁷.0¹²,¹⁶]heptadecan-8-one

> <ALOGPS_LOGP>
5.42

> <JCHEM_LOGP>
5.388844630000001

> <ALOGPS_LOGS>
-6.51

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.325328794304458

> <JCHEM_PKA_STRONGEST_BASIC>
-3.093901185371231

> <JCHEM_POLAR_SURFACE_AREA>
55.76

> <JCHEM_REFRACTIVITY>
134.43669999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.45e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
13-[5-(2-hydroxypropan-2-yl)-2-methyloxolan-2-yl]-1,5,16-trimethyl-4-(prop-1-en-2-yl)-9-oxatetracyclo[8.6.1.0⁵,¹⁷.0¹²,¹⁶]heptadecan-8-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 19-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   19-APR-15         0                                  
HETATM    1  C   UNK     0      -2.776  -4.554   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -2.703  -3.015   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -3.998  -2.182   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.000  -3.080   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.667  -1.540   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -0.000  -0.000   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.132   2.016   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       5.037   0.770   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.132  -0.476   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       2.667  -0.000   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       3.294  -1.407   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       4.608   3.481   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       3.102   3.801   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       6.015   2.854   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       7.045   3.999   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       6.275   5.332   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       4.769   5.012   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0       6.902   6.739   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       7.528   8.146   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       5.495   7.365   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0       8.308   6.113   0.000  0.00  0.00           O+0
HETATM   28  O   UNK     0      -1.204   2.500   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0      -2.705   2.157   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0      -3.666   3.362   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0      -3.374   0.770   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      -2.705  -0.617   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      -1.204  -0.960   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      -2.453  -1.862   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5   33                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8    9   16                                             
CONECT    8    7                                                            
CONECT    9    7   10   33                                                  
CONECT   10    9   11   28                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13   16                                                  
CONECT   13   12   14   18                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15    7   12   17                                             
CONECT   17   16                                                            
CONECT   18   13   19   20   23                                             
CONECT   19   18                                                            
CONECT   20   18   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   23   24                                                  
CONECT   23   22   18                                                       
CONECT   24   22   25   26   27                                             
CONECT   25   24                                                            
CONECT   26   24                                                            
CONECT   27   24                                                            
CONECT   28   10   29                                                       
CONECT   29   28   30   31                                                  
CONECT   30   29                                                            
CONECT   31   29   32                                                       
CONECT   32   31   33                                                       
CONECT   33   32    4    9   34                                             
CONECT   34   33                                                            
MASTER        0    0    0    0    0    0    0    0   34    0   76    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₃₀H₄₈O₄

Average Mass

472.7100 Da

Monoisotopic Mass

472.35526 Da

IUPAC Name

13-[5-(2-hydroxypropan-2-yl)-2-methyloxolan-2-yl]-1,5,16-trimethyl-4-(prop-1-en-2-yl)-9-oxatetracyclo[8.6.1.0⁵,¹⁷.0¹²,¹⁶]heptadecan-8-one

Traditional Name

13-[5-(2-hydroxypropan-2-yl)-2-methyloxolan-2-yl]-1,5,16-trimethyl-4-(prop-1-en-2-yl)-9-oxatetracyclo[8.6.1.0⁵,¹⁷.0¹²,¹⁶]heptadecan-8-one

CAS Registry Number

Not Available

SMILES

CC(=C)C1CCC2(C)C3C(CC4C(CCC24C)C2(C)CCC(O2)C(C)(C)O)OC(=O)CCC13C

InChI Identifier

InChI=1S/C30H48O4/c1-18(2)19-9-15-29(7)25-22(33-24(31)12-13-27(19,25)5)17-21-20(10-14-28(21,29)6)30(8)16-11-23(34-30)26(3,4)32/h19-23,25,32H,1,9-17H2,2-8H3

InChI Key

SEBLWBUGZCPRKV-UHFFFAOYSA-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
Betula ovalifolia	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as terpene glycosides. These are prenol lipids containing a carbohydrate moiety glycosidically bound to a terpene backbone.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Terpene glycosides

Direct Parent

Terpene glycosides

Alternative Parents

Substituents

Terpene glycoside
Terpene lactone
Sesquiterpenoid
Caprolactone
Oxepane
Tertiary alcohol
Tetrahydrofuran
Lactone
Carboxylic acid ester
Organoheterocyclic compound
Oxacycle
Monocarboxylic acid or derivatives
Ether
Dialkyl ether
Carboxylic acid derivative
Hydrocarbon derivative
Organic oxide
Organooxygen compound
Carbonyl group
Organic oxygen compound
Alcohol
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic 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	5.42	ALOGPS
logP	5.39	ChemAxon
logS	-6.5	ALOGPS
pKa (Strongest Acidic)	14.33	ChemAxon
pKa (Strongest Basic)	-3.1	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	55.76 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	134.44 m³·mol⁻¹	ChemAxon
Polarizability	55.41 Å³	ChemAxon
Number of Rings	5	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

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

85163406

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 13-[5-(2-hydroxypropan-2-yl)-2-methyloxolan-2-yl]-1,5,16-trimethyl-4-(prop-1-en-2-yl)-9-oxatetracyclo[8.6.1.0⁵,¹⁷.0¹²,¹⁶]heptadecan-8-one (NP0304721)

MOL for NP0304721 (13-[5-(2-hydroxypropan-2-yl)-2-methyloxolan-2-yl]-1,5,16-trimethyl-4-(prop-1-en-2-yl)-9-oxatetracyclo[8.6.1.0⁵,¹⁷.0¹²,¹⁶]heptadecan-8-one)

3D MOL for NP0304721 (13-[5-(2-hydroxypropan-2-yl)-2-methyloxolan-2-yl]-1,5,16-trimethyl-4-(prop-1-en-2-yl)-9-oxatetracyclo[8.6.1.0⁵,¹⁷.0¹²,¹⁶]heptadecan-8-one)

3D SDF for NP0304721 (13-[5-(2-hydroxypropan-2-yl)-2-methyloxolan-2-yl]-1,5,16-trimethyl-4-(prop-1-en-2-yl)-9-oxatetracyclo[8.6.1.0⁵,¹⁷.0¹²,¹⁶]heptadecan-8-one)

3D-SDF for NP0304721 (13-[5-(2-hydroxypropan-2-yl)-2-methyloxolan-2-yl]-1,5,16-trimethyl-4-(prop-1-en-2-yl)-9-oxatetracyclo[8.6.1.0⁵,¹⁷.0¹²,¹⁶]heptadecan-8-one)

PDB for NP0304721 (13-[5-(2-hydroxypropan-2-yl)-2-methyloxolan-2-yl]-1,5,16-trimethyl-4-(prop-1-en-2-yl)-9-oxatetracyclo[8.6.1.0⁵,¹⁷.0¹²,¹⁶]heptadecan-8-one)

3D PDB for NP0304721 (13-[5-(2-hydroxypropan-2-yl)-2-methyloxolan-2-yl]-1,5,16-trimethyl-4-(prop-1-en-2-yl)-9-oxatetracyclo[8.6.1.0⁵,¹⁷.0¹²,¹⁶]heptadecan-8-one)

SMILES for NP0304721 (13-[5-(2-hydroxypropan-2-yl)-2-methyloxolan-2-yl]-1,5,16-trimethyl-4-(prop-1-en-2-yl)-9-oxatetracyclo[8.6.1.0⁵,¹⁷.0¹²,¹⁶]heptadecan-8-one)

INCHI for NP0304721 (13-[5-(2-hydroxypropan-2-yl)-2-methyloxolan-2-yl]-1,5,16-trimethyl-4-(prop-1-en-2-yl)-9-oxatetracyclo[8.6.1.0⁵,¹⁷.0¹²,¹⁶]heptadecan-8-one)

Structure for NP0304721 (13-[5-(2-hydroxypropan-2-yl)-2-methyloxolan-2-yl]-1,5,16-trimethyl-4-(prop-1-en-2-yl)-9-oxatetracyclo[8.6.1.0⁵,¹⁷.0¹²,¹⁶]heptadecan-8-one)

3D Structure for NP0304721 (13-[5-(2-hydroxypropan-2-yl)-2-methyloxolan-2-yl]-1,5,16-trimethyl-4-(prop-1-en-2-yl)-9-oxatetracyclo[8.6.1.0⁵,¹⁷.0¹²,¹⁶]heptadecan-8-one)