NP-MRD: Showing NP-Card for Deacetylnomilinic acid (NP0084801)

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Record Information

Version

2.0

Created at

2022-04-29 05:26:46 UTC

Updated at

2022-04-29 05:26:46 UTC

NP-MRD ID

NP0084801

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Deacetylnomilinic acid

Description

Deacetylnomilinic acid belongs to the class of organic compounds known as steroid lactones. These are sterol lipids containing a lactone moiety linked to the steroid skeleton. Deacetylnomilinic acid is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, deacetylnomilinic acid has been detected, but not quantified in, citrus. Deacetylnomilinic acid is found in Citrus ichangensis and Citrus paradisi . This could make deacetylnomilinic acid a potential biomarker for the consumption of these foods.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv0541 05061308132D          

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M  END

     RDKit          3D

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M  END


  Mrv0541 05061308132D          

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M  END
> <DATABASE_ID>
NP0084801

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)(O)C1CC(=O)C2(C)C(CCC3(C)C(OC(=O)C4OC234)C2=COC=C2)C1(C)C(O)CC(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C26H34O9/c1-22(2,32)15-10-17(28)25(5)14(24(15,4)16(27)11-18(29)30)6-8-23(3)19(13-7-9-33-12-13)34-21(31)20-26(23,25)35-20/h7,9,12,14-16,19-20,27,32H,6,8,10-11H2,1-5H3,(H,29,30)

> <INCHI_KEY>
OZOFRBKHLATMMU-UHFFFAOYSA-N

> <FORMULA>
C26H34O9

> <MOLECULAR_WEIGHT>
490.5428

> <EXACT_MASS>
490.220282686

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_AVERAGE_POLARIZABILITY>
49.80201998616127

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
3-[11-(furan-3-yl)-5-(2-hydroxypropan-2-yl)-2,6,10-trimethyl-3,13-dioxo-12,15-dioxatetracyclo[8.5.0.0¹,¹⁴.0²,⁷]pentadecan-6-yl]-3-hydroxypropanoic acid

> <ALOGPS_LOGP>
2.17

> <JCHEM_LOGP>
1.9117876006666648

> <ALOGPS_LOGS>
-3.58

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
14.527929761269608

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.137843125710504

> <JCHEM_PKA_STRONGEST_BASIC>
-2.7854693343267636

> <JCHEM_POLAR_SURFACE_AREA>
146.79999999999998

> <JCHEM_REFRACTIVITY>
119.94679999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.28e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3-[11-(furan-3-yl)-5-(2-hydroxypropan-2-yl)-2,6,10-trimethyl-3,13-dioxo-12,15-dioxatetracyclo[8.5.0.0¹,¹⁴.0²,⁷]pentadecan-6-yl]-3-hydroxypropanoic acid

> <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      -0.058   2.325   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.433  -0.727   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       7.339  -0.933   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.069   1.401   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.158  -1.024   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.672   0.607   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      10.079  -2.330   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       6.005  -0.163   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      11.110  -1.185   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.671  -1.703   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.467   3.234   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       8.834  -0.172   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       8.673  -1.703   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       3.338  -0.163   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       0.671  -0.163   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       2.994   1.786   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       2.004  -2.473   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       3.457   4.413   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       7.339  -2.473   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       4.672  -4.013   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       6.005  -4.783   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -0.663   0.607   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       6.005  -1.703   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       2.004   0.607   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       3.338  -1.703   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       4.672  -2.473   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0       4.511   1.519   0.000  0.00  0.00           O+0
HETATM   28  O   UNK     0       2.004  -4.013   0.000  0.00  0.00           O+0
HETATM   29  O   UNK     0       2.931   5.860   0.000  0.00  0.00           O+0
HETATM   30  O   UNK     0       4.974   4.146   0.000  0.00  0.00           O+0
HETATM   31  O   UNK     0       6.005  -6.323   0.000  0.00  0.00           O+0
HETATM   32  O   UNK     0      -1.997   1.377   0.000  0.00  0.00           O+0
HETATM   33  O   UNK     0      10.340   0.148   0.000  0.00  0.00           O+0
HETATM   34  O   UNK     0       7.339  -4.013   0.000  0.00  0.00           O+0
HETATM   35  O   UNK     0       3.338  -3.243   0.000  0.00  0.00           O+0
CONECT    1   22                                                            
CONECT    2   22                                                            
CONECT    3   23                                                            
CONECT    4   24                                                            
CONECT    5   25                                                            
CONECT    6    8   14                                                       
CONECT    7    9   13                                                       
CONECT    8    6   23                                                       
CONECT    9    7   33                                                       
CONECT   10   15   17                                                       
CONECT   11   16   18                                                       
CONECT   12   13   33                                                       
CONECT   13    7   12   19                                                  
CONECT   14    6   24   25                                                  
CONECT   15   10   22   24                                                  
CONECT   16   11   24   27                                                  
CONECT   17   10   25   28                                                  
CONECT   18   11   29   30                                                  
CONECT   19   13   23   34                                                  
CONECT   20   21   26   35                                                  
CONECT   21   20   31   34                                                  
CONECT   22    1    2   15   32                                             
CONECT   23    3    8   19   26                                             
CONECT   24    4   14   15   16                                             
CONECT   25    5   14   17   26                                             
CONECT   26   20   23   25   35                                             
CONECT   27   16                                                            
CONECT   28   17                                                            
CONECT   29   18                                                            
CONECT   30   18                                                            
CONECT   31   21                                                            
CONECT   32   22                                                            
CONECT   33    9   12                                                       
CONECT   34   19   21                                                       
CONECT   35   20   26                                                       
MASTER        0    0    0    0    0    0    0    0   35    0   78    0
END

View in JSmol

Synonyms

Value	Source
Deacetylnomilinate	Generator
3-[11-(Furan-3-yl)-5-(2-hydroxypropan-2-yl)-2,6,10-trimethyl-3,13-dioxo-12,15-dioxatetracyclo[8.5.0.0¹,¹⁴.0²,⁷]pentadecan-6-yl]-3-hydroxypropanoate	Generator

Chemical Formula

C₂₆H₃₄O₉

Average Mass

490.5428 Da

Monoisotopic Mass

490.22028 Da

IUPAC Name

3-[11-(furan-3-yl)-5-(2-hydroxypropan-2-yl)-2,6,10-trimethyl-3,13-dioxo-12,15-dioxatetracyclo[8.5.0.0¹,¹⁴.0²,⁷]pentadecan-6-yl]-3-hydroxypropanoic acid

Traditional Name

3-[11-(furan-3-yl)-5-(2-hydroxypropan-2-yl)-2,6,10-trimethyl-3,13-dioxo-12,15-dioxatetracyclo[8.5.0.0¹,¹⁴.0²,⁷]pentadecan-6-yl]-3-hydroxypropanoic acid

CAS Registry Number

Not Available

SMILES

CC(C)(O)C1CC(=O)C2(C)C(CCC3(C)C(OC(=O)C4OC234)C2=COC=C2)C1(C)C(O)CC(O)=O

InChI Identifier

InChI=1S/C26H34O9/c1-22(2,32)15-10-17(28)25(5)14(24(15,4)16(27)11-18(29)30)6-8-23(3)19(13-7-9-33-12-13)34-21(31)20-26(23,25)35-20/h7,9,12,14-16,19-20,27,32H,6,8,10-11H2,1-5H3,(H,29,30)

InChI Key

OZOFRBKHLATMMU-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, 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
Citrus ichangensis	Plant	KNApSAcK
Citrus paradisi	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as steroid lactones. These are sterol lipids containing a lactone moiety linked to the steroid skeleton.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Steroid lactones

Direct Parent

Steroid lactones

Alternative Parents

Not Available

Substituents

Not Available

Molecular Framework

Aromatic 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	2.17	ALOGPS
logP	1.91	ChemAxon
logS	-3.6	ALOGPS
pKa (Strongest Acidic)	4.14	ChemAxon
pKa (Strongest Basic)	-2.8	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	146.8 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	119.95 m³·mol⁻¹	ChemAxon
Polarizability	49.8 Å³	ChemAxon
Number of Rings	5	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

HMDB0035073

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB013697

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

13857951

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Showing NP-Card for Deacetylnomilinic acid (NP0084801)

MOL for NP0084801 (Deacetylnomilinic acid)

3D MOL for NP0084801 (Deacetylnomilinic acid)

3D SDF for NP0084801 (Deacetylnomilinic acid)

3D-SDF for NP0084801 (Deacetylnomilinic acid)

PDB for NP0084801 (Deacetylnomilinic acid)

3D PDB for NP0084801 (Deacetylnomilinic acid)

SMILES for NP0084801 (Deacetylnomilinic acid)

INCHI for NP0084801 (Deacetylnomilinic acid)

Structure for NP0084801 (Deacetylnomilinic acid)

3D Structure for NP0084801 (Deacetylnomilinic acid)