NP-MRD: Showing NP-Card for 16-(furan-3-yl)-3,12-dihydroxy-5,5,11,17-tetramethyl-7,10,15,21-tetraoxaheptacyclo[11.8.1.0¹,²⁰.0³,¹².0⁶,⁸.0⁶,¹¹.0¹⁷,²²]docos-13(22)-ene-4,9,14-trione (NP0157851)

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Record Information

Version

2.0

Created at

2022-09-02 15:20:21 UTC

Updated at

2022-09-02 15:20:21 UTC

NP-MRD ID

NP0157851

Secondary Accession Numbers

None

Natural Product Identification

Common Name

16-(furan-3-yl)-3,12-dihydroxy-5,5,11,17-tetramethyl-7,10,15,21-tetraoxaheptacyclo[11.8.1.0¹,²⁰.0³,¹².0⁶,⁸.0⁶,¹¹.0¹⁷,²²]docos-13(22)-ene-4,9,14-trione

Description

(S)-10-Nonacosanol belongs to the class of organic compounds known as long-chain fatty alcohols. These are fatty alcohols that have an aliphatic tail of 13 to 21 carbon atoms. Thus, (S)-10-nonacosanol is considered to be a fatty alcohol lipid molecule. A fatty alcohol that is nonacosane substituted by a hydroxy group at position 10 (S)-10-Nonacosanol is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Outside of the human body, (S)-10-Nonacosanol has been detected, but not quantified in, fats and oils. 16-(furan-3-yl)-3,12-dihydroxy-5,5,11,17-tetramethyl-7,10,15,21-tetraoxaheptacyclo[11.8.1.0¹,²⁰.0³,¹².0⁶,⁸.0⁶,¹¹.0¹⁷,²²]docos-13(22)-ene-4,9,14-trione is found in Lansium domesticum. This could make (S)-10-nonacosanol a potential biomarker for the consumption of these foods.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv0541 05061308372D          

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M  END

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  Mrv0541 05061308372D          

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 36 22  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0157851

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC12OC(=O)C3OC13C(C)(C)C(=O)C1(O)CC34OC3CCC3(C)C(OC(=O)C(=C43)C21O)C1=COC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C26H26O10/c1-20(2)19(29)24(30)10-23-12(34-23)5-7-21(3)14(23)13(17(27)33-15(21)11-6-8-32-9-11)25(24,31)22(4)26(20)16(35-26)18(28)36-22/h6,8-9,12,15-16,30-31H,5,7,10H2,1-4H3

> <INCHI_KEY>
CDCHBVSDWNDPOE-UHFFFAOYSA-N

> <FORMULA>
C26H26O10

> <MOLECULAR_WEIGHT>
498.4786

> <EXACT_MASS>
498.152597052

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_AVERAGE_POLARIZABILITY>
48.21807502584771

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
16-(furan-3-yl)-3,12-dihydroxy-5,5,11,17-tetramethyl-7,10,15,21-tetraoxaheptacyclo[11.8.1.0¹,²⁰.0³,¹².0⁶,⁸.0⁶,¹¹.0¹⁷,²²]docos-13(22)-ene-4,9,14-trione

> <ALOGPS_LOGP>
1.70

> <JCHEM_LOGP>
1.1404675569999987

> <ALOGPS_LOGS>
-2.87

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
8

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.683353622945717

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.327091742477279

> <JCHEM_PKA_STRONGEST_BASIC>
-3.128548870153771

> <JCHEM_POLAR_SURFACE_AREA>
148.32999999999998

> <JCHEM_REFRACTIVITY>
115.62109999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.67e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
16-(furan-3-yl)-3,12-dihydroxy-5,5,11,17-tetramethyl-7,10,15,21-tetraoxaheptacyclo[11.8.1.0¹,²⁰.0³,¹².0⁶,⁸.0⁶,¹¹.0¹⁷,²²]docos-13(22)-ene-4,9,14-trione

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 06-MAY-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAY-13         0                                  
HETATM    1  C   UNK     0       5.471   5.293   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       6.668   3.717   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      14.561   9.280   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       8.449   9.118   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      14.948   6.224   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      15.842  10.363   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      14.754   7.752   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      16.720  11.628   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      14.335  12.347   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      11.075   4.958   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      14.367  10.808   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      13.721   5.293   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      10.688   8.013   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      12.108   7.417   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      13.141   9.876   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       5.551   7.625   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      10.495   9.541   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       5.995   9.100   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       8.429   4.623   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       7.009   5.219   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      13.335   8.348   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       8.042   7.678   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      12.302   5.889   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       9.655   5.554   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       9.462   7.082   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       6.816   6.747   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0       9.075  10.137   0.000  0.00  0.00           O+0
HETATM   28  O   UNK     0       5.064  10.326   0.000  0.00  0.00           O+0
HETATM   29  O   UNK     0       8.623   3.095   0.000  0.00  0.00           O+0
HETATM   30  O   UNK     0       9.849   4.026   0.000  0.00  0.00           O+0
HETATM   31  O   UNK     0       9.763   8.720   0.000  0.00  0.00           O+0
HETATM   32  O   UNK     0      15.789  12.854   0.000  0.00  0.00           O+0
HETATM   33  O   UNK     0      11.721  10.473   0.000  0.00  0.00           O+0
HETATM   34  O   UNK     0      12.495   4.361   0.000  0.00  0.00           O+0
HETATM   35  O   UNK     0       5.422   6.091   0.000  0.00  0.00           O+0
HETATM   36  O   UNK     0       7.535   9.132   0.000  0.00  0.00           O+0
CONECT    1   20                                                            
CONECT    2   20                                                            
CONECT    3   21                                                            
CONECT    4   22                                                            
CONECT    5    7   12                                                       
CONECT    6    8   11                                                       
CONECT    7    5   21                                                       
CONECT    8    6   32                                                       
CONECT    9   11   32                                                       
CONECT   10   23   24                                                       
CONECT   11    6    9   15                                                  
CONECT   12    5   23   34                                                  
CONECT   13   14   17   25                                                  
CONECT   14   13   21   23                                                  
CONECT   15   11   21   33                                                  
CONECT   16   18   26   35                                                  
CONECT   17   13   27   33                                                  
CONECT   18   16   28   36                                                  
CONECT   19   20   24   29                                                  
CONECT   20    1    2   19   26                                             
CONECT   21    3    7   14   15                                             
CONECT   22    4   25   26   36                                             
CONECT   23   10   12   14   34                                             
CONECT   24   10   19   25   30                                             
CONECT   25   13   22   24   31                                             
CONECT   26   16   20   22   35                                             
CONECT   27   17                                                            
CONECT   28   18                                                            
CONECT   29   19                                                            
CONECT   30   24                                                            
CONECT   31   25                                                            
CONECT   32    8    9                                                       
CONECT   33   15   17                                                       
CONECT   34   12   23                                                       
CONECT   35   16   26                                                       
CONECT   36   18   22                                                       
MASTER        0    0    0    0    0    0    0    0   36    0   86    0
END

View in JSmol

Synonyms

Value	Source
10-Nonacosanol	HMDB

Chemical Formula

C₂₆H₂₆O₁₀

Average Mass

498.4786 Da

Monoisotopic Mass

498.15260 Da

IUPAC Name

16-(furan-3-yl)-3,12-dihydroxy-5,5,11,17-tetramethyl-7,10,15,21-tetraoxaheptacyclo[11.8.1.0¹,²⁰.0³,¹².0⁶,⁸.0⁶,¹¹.0¹⁷,²²]docos-13(22)-ene-4,9,14-trione

Traditional Name

16-(furan-3-yl)-3,12-dihydroxy-5,5,11,17-tetramethyl-7,10,15,21-tetraoxaheptacyclo[11.8.1.0¹,²⁰.0³,¹².0⁶,⁸.0⁶,¹¹.0¹⁷,²²]docos-13(22)-ene-4,9,14-trione

CAS Registry Number

Not Available

SMILES

CC12OC(=O)C3OC13C(C)(C)C(=O)C1(O)CC34OC3CCC3(C)C(OC(=O)C(=C43)C21O)C1=COC=C1

InChI Identifier

InChI=1S/C26H26O10/c1-20(2)19(29)24(30)10-23-12(34-23)5-7-21(3)14(23)13(17(27)33-15(21)11-6-8-32-9-11)25(24,31)22(4)26(20)16(35-26)18(28)36-22/h6,8-9,12,15-16,30-31H,5,7,10H2,1-4H3

InChI Key

CDCHBVSDWNDPOE-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
Lansium domesticum	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as long-chain fatty alcohols. These are fatty alcohols that have an aliphatic tail of 13 to 21 carbon atoms.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Fatty alcohols

Direct Parent

Long-chain fatty alcohols

Alternative Parents

Substituents

Long chain fatty alcohol
Secondary alcohol
Organic oxygen compound
Hydrocarbon derivative
Organooxygen compound
Alcohol
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

fatty alcohol (CHEBI:7611 )
Fatty alcohols (LMFA05000098 )

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	1.7	ALOGPS
logP	1.14	ChemAxon
logS	-2.9	ALOGPS
pKa (Strongest Acidic)	11.33	ChemAxon
pKa (Strongest Basic)	-3.1	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	148.33 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	115.62 m³·mol⁻¹	ChemAxon
Polarizability	48.22 Å³	ChemAxon
Number of Rings	8	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0034287

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB012625

KNApSAcK ID

Not Available

Chemspider ID

10752065

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

25240035

PDB ID

Not Available

ChEBI ID

7611

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 16-(furan-3-yl)-3,12-dihydroxy-5,5,11,17-tetramethyl-7,10,15,21-tetraoxaheptacyclo[11.8.1.0¹,²⁰.0³,¹².0⁶,⁸.0⁶,¹¹.0¹⁷,²²]docos-13(22)-ene-4,9,14-trione (NP0157851)

MOL for NP0157851 (16-(furan-3-yl)-3,12-dihydroxy-5,5,11,17-tetramethyl-7,10,15,21-tetraoxaheptacyclo[11.8.1.0¹,²⁰.0³,¹².0⁶,⁸.0⁶,¹¹.0¹⁷,²²]docos-13(22)-ene-4,9,14-trione)

3D MOL for NP0157851 (16-(furan-3-yl)-3,12-dihydroxy-5,5,11,17-tetramethyl-7,10,15,21-tetraoxaheptacyclo[11.8.1.0¹,²⁰.0³,¹².0⁶,⁸.0⁶,¹¹.0¹⁷,²²]docos-13(22)-ene-4,9,14-trione)

3D SDF for NP0157851 (16-(furan-3-yl)-3,12-dihydroxy-5,5,11,17-tetramethyl-7,10,15,21-tetraoxaheptacyclo[11.8.1.0¹,²⁰.0³,¹².0⁶,⁸.0⁶,¹¹.0¹⁷,²²]docos-13(22)-ene-4,9,14-trione)

3D-SDF for NP0157851 (16-(furan-3-yl)-3,12-dihydroxy-5,5,11,17-tetramethyl-7,10,15,21-tetraoxaheptacyclo[11.8.1.0¹,²⁰.0³,¹².0⁶,⁸.0⁶,¹¹.0¹⁷,²²]docos-13(22)-ene-4,9,14-trione)

PDB for NP0157851 (16-(furan-3-yl)-3,12-dihydroxy-5,5,11,17-tetramethyl-7,10,15,21-tetraoxaheptacyclo[11.8.1.0¹,²⁰.0³,¹².0⁶,⁸.0⁶,¹¹.0¹⁷,²²]docos-13(22)-ene-4,9,14-trione)

3D PDB for NP0157851 (16-(furan-3-yl)-3,12-dihydroxy-5,5,11,17-tetramethyl-7,10,15,21-tetraoxaheptacyclo[11.8.1.0¹,²⁰.0³,¹².0⁶,⁸.0⁶,¹¹.0¹⁷,²²]docos-13(22)-ene-4,9,14-trione)

SMILES for NP0157851 (16-(furan-3-yl)-3,12-dihydroxy-5,5,11,17-tetramethyl-7,10,15,21-tetraoxaheptacyclo[11.8.1.0¹,²⁰.0³,¹².0⁶,⁸.0⁶,¹¹.0¹⁷,²²]docos-13(22)-ene-4,9,14-trione)

INCHI for NP0157851 (16-(furan-3-yl)-3,12-dihydroxy-5,5,11,17-tetramethyl-7,10,15,21-tetraoxaheptacyclo[11.8.1.0¹,²⁰.0³,¹².0⁶,⁸.0⁶,¹¹.0¹⁷,²²]docos-13(22)-ene-4,9,14-trione)

Structure for NP0157851 (16-(furan-3-yl)-3,12-dihydroxy-5,5,11,17-tetramethyl-7,10,15,21-tetraoxaheptacyclo[11.8.1.0¹,²⁰.0³,¹².0⁶,⁸.0⁶,¹¹.0¹⁷,²²]docos-13(22)-ene-4,9,14-trione)

3D Structure for NP0157851 (16-(furan-3-yl)-3,12-dihydroxy-5,5,11,17-tetramethyl-7,10,15,21-tetraoxaheptacyclo[11.8.1.0¹,²⁰.0³,¹².0⁶,⁸.0⁶,¹¹.0¹⁷,²²]docos-13(22)-ene-4,9,14-trione)