NP-MRD: Showing NP-Card for 5-{[6,11-dihydroxy-15-(2-hydroxypropan-2-yl)-5,12-dimethyl-4-oxatricyclo[10.3.0.0³,⁵]pentadec-9-en-9-yl]methoxy}-3-hydroxy-3-methyl-5-oxopentanoic acid (NP0210088)

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Record Information

Version

2.0

Created at

2022-09-05 07:45:22 UTC

Updated at

2022-09-05 07:45:22 UTC

NP-MRD ID

NP0210088

Secondary Accession Numbers

None

Natural Product Identification

Common Name

5-{[6,11-dihydroxy-15-(2-hydroxypropan-2-yl)-5,12-dimethyl-4-oxatricyclo[10.3.0.0³,⁵]pentadec-9-en-9-yl]methoxy}-3-hydroxy-3-methyl-5-oxopentanoic acid

Description

5-{[6,11-Dihydroxy-15-(2-hydroxypropan-2-yl)-5,12-dimethyl-4-oxatricyclo[10.3.0.0³,⁵]Pentadec-9-en-9-yl]methoxy}-3-hydroxy-3-methyl-5-oxopentanoic acid belongs to the class of organic compounds known as heterocyclic fatty acids. These are fatty acids containing a heterocyclic attached to the acyl chain. 5-{[6,11-Dihydroxy-15-(2-hydroxypropan-2-yl)-5,12-dimethyl-4-oxatricyclo[10.3.0.0³,⁵]Pentadec-9-en-9-yl]methoxy}-3-hydroxy-3-methyl-5-oxopentanoic acid is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004171518352D          

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M  END

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M  END


  Mrv1533004171518352D          

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  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  8 10  1  0  0  0  0
 10 11  1  0  0  0  0
 12 10  1  4  0  0  0
 12 13  2  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
 16 17  2  0  0  0  0
 16 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 19 21  1  0  0  0  0
 19 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  2  0  0  0  0
 23 25  1  0  0  0  0
 13 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 28 30  1  0  0  0  0
 30 31  1  0  0  0  0
 30 32  1  0  0  0  0
 32 33  1  0  0  0  0
 30 33  1  0  0  0  0
 33 34  1  0  0  0  0
 34 35  1  0  0  0  0
  5 35  1  0  0  0  0
  8 35  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0210088

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(O)(CC(O)=O)CC(=O)OCC1=CC(O)C2(C)CCC(C2CC2OC2(C)C(O)CC1)C(C)(C)O

> <INCHI_IDENTIFIER>
InChI=1S/C26H42O9/c1-23(2,32)16-8-9-25(4)17(16)11-20-26(5,35-20)18(27)7-6-15(10-19(25)28)14-34-22(31)13-24(3,33)12-21(29)30/h10,16-20,27-28,32-33H,6-9,11-14H2,1-5H3,(H,29,30)

> <INCHI_KEY>
OFJYPZDJODKQBK-UHFFFAOYSA-N

> <FORMULA>
C26H42O9

> <MOLECULAR_WEIGHT>
498.613

> <EXACT_MASS>
498.282882932

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_ATOM_COUNT>
77

> <JCHEM_AVERAGE_POLARIZABILITY>
52.82856053289601

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
5-{[6,11-dihydroxy-15-(2-hydroxypropan-2-yl)-5,12-dimethyl-4-oxatricyclo[10.3.0.0³,⁵]pentadec-9-en-9-yl]methoxy}-3-hydroxy-3-methyl-5-oxopentanoic acid

> <ALOGPS_LOGP>
1.19

> <JCHEM_LOGP>
0.7183785273333338

> <ALOGPS_LOGS>
-3.51

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
13.726910541082816

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.075017616433515

> <JCHEM_PKA_STRONGEST_BASIC>
-0.8402293833864626

> <JCHEM_POLAR_SURFACE_AREA>
157.05

> <JCHEM_REFRACTIVITY>
127.14029999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.55e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
5-{[6,11-dihydroxy-15-(2-hydroxypropan-2-yl)-5,12-dimethyl-4-oxatricyclo[10.3.0.0³,⁵]pentadec-9-en-9-yl]methoxy}-3-hydroxy-3-methyl-5-oxopentanoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 17-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   17-APR-15         0                                  
HETATM    1  C   UNK     0       6.420  -7.182   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       5.523  -5.930   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       6.775  -5.033   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       4.271  -6.827   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       4.627  -4.678   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       3.087  -4.667   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.621  -3.199   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       3.873  -2.303   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.545  -1.524   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.045  -0.772   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       2.786   0.114   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       5.558  -0.031   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       6.194   1.371   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       5.433   2.710   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       6.213   4.039   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       5.452   5.378   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       3.912   5.388   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       6.231   6.706   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       5.470   8.045   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       6.809   8.806   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       4.131   7.284   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       4.710   9.384   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       5.489  10.712   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       4.728  12.051   0.000  0.00  0.00           O+0
HETATM   25  O   UNK     0       7.029  10.701   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0       7.725   1.200   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       8.034  -0.309   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       9.346  -1.367   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0      10.770  -0.781   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0       9.175  -2.897   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      10.705  -3.069   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0       9.003  -4.428   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0       7.764  -3.514   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       6.524  -2.600   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       5.113  -3.217   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    4    5                                             
CONECT    3    2                                                            
CONECT    4    2                                                            
CONECT    5    2    6   35                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9   10   35                                             
CONECT    9    8                                                            
CONECT   10    8   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10   13                                                       
CONECT   13   12   14   26                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16   19                                                       
CONECT   19   18   20   21   22                                             
CONECT   20   19                                                            
CONECT   21   19                                                            
CONECT   22   19   23                                                       
CONECT   23   22   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23                                                            
CONECT   26   13   27                                                       
CONECT   27   26   28                                                       
CONECT   28   27   29   30                                                  
CONECT   29   28                                                            
CONECT   30   28   31   32   33                                             
CONECT   31   30                                                            
CONECT   32   30   33                                                       
CONECT   33   32   30   34                                                  
CONECT   34   33   35                                                       
CONECT   35   34    5    8                                                  
MASTER        0    0    0    0    0    0    0    0   35    0   74    0
END

View in JSmol

Synonyms

Value	Source
5-{[6,11-dihydroxy-15-(2-hydroxypropan-2-yl)-5,12-dimethyl-4-oxatricyclo[10.3.0.0,]pentadec-9-en-9-yl]methoxy}-3-hydroxy-3-methyl-5-oxopentanoate	Generator
5-{[6,11-dihydroxy-15-(2-hydroxypropan-2-yl)-5,12-dimethyl-4-oxatricyclo[10.3.0.0³,⁵]pentadec-9-en-9-yl]methoxy}-3-hydroxy-3-methyl-5-oxopentanoate	Generator

Chemical Formula

C₂₆H₄₂O₉

Average Mass

498.6130 Da

Monoisotopic Mass

498.28288 Da

IUPAC Name

5-{[6,11-dihydroxy-15-(2-hydroxypropan-2-yl)-5,12-dimethyl-4-oxatricyclo[10.3.0.0³,⁵]pentadec-9-en-9-yl]methoxy}-3-hydroxy-3-methyl-5-oxopentanoic acid

Traditional Name

5-{[6,11-dihydroxy-15-(2-hydroxypropan-2-yl)-5,12-dimethyl-4-oxatricyclo[10.3.0.0³,⁵]pentadec-9-en-9-yl]methoxy}-3-hydroxy-3-methyl-5-oxopentanoic acid

CAS Registry Number

Not Available

SMILES

CC(O)(CC(O)=O)CC(=O)OCC1=CC(O)C2(C)CCC(C2CC2OC2(C)C(O)CC1)C(C)(C)O

InChI Identifier

InChI=1S/C26H42O9/c1-23(2,32)16-8-9-25(4)17(16)11-20-26(5,35-20)18(27)7-6-15(10-19(25)28)14-34-22(31)13-24(3,33)12-21(29)30/h10,16-20,27-28,32-33H,6-9,11-14H2,1-5H3,(H,29,30)

InChI Key

OFJYPZDJODKQBK-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

Not Available

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as heterocyclic fatty acids. These are fatty acids containing a heterocyclic attached to the acyl chain.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Fatty acids and conjugates

Direct Parent

Heterocyclic fatty acids

Alternative Parents

Substituents

Branched fatty acid
Fatty acid ester
Heterocyclic fatty acid
Hydroxy fatty acid
Short-chain hydroxy acid
Methyl-branched fatty acid
Dicarboxylic acid or derivatives
Tertiary alcohol
Carboxylic acid ester
Secondary alcohol
Oxacycle
Organoheterocyclic compound
Carboxylic acid derivative
Carboxylic acid
Dialkyl ether
Oxirane
Ether
Organic oxide
Organooxygen compound
Hydrocarbon derivative
Organic oxygen compound
Alcohol
Carbonyl group
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	1.19	ALOGPS
logP	0.72	ChemAxon
logS	-3.5	ALOGPS
pKa (Strongest Acidic)	4.08	ChemAxon
pKa (Strongest Basic)	-0.84	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	157.05 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	127.14 m³·mol⁻¹	ChemAxon
Polarizability	52.83 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	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

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 5-{[6,11-dihydroxy-15-(2-hydroxypropan-2-yl)-5,12-dimethyl-4-oxatricyclo[10.3.0.0³,⁵]pentadec-9-en-9-yl]methoxy}-3-hydroxy-3-methyl-5-oxopentanoic acid (NP0210088)

MOL for NP0210088 (5-{[6,11-dihydroxy-15-(2-hydroxypropan-2-yl)-5,12-dimethyl-4-oxatricyclo[10.3.0.0³,⁵]pentadec-9-en-9-yl]methoxy}-3-hydroxy-3-methyl-5-oxopentanoic acid)

3D MOL for NP0210088 (5-{[6,11-dihydroxy-15-(2-hydroxypropan-2-yl)-5,12-dimethyl-4-oxatricyclo[10.3.0.0³,⁵]pentadec-9-en-9-yl]methoxy}-3-hydroxy-3-methyl-5-oxopentanoic acid)

3D SDF for NP0210088 (5-{[6,11-dihydroxy-15-(2-hydroxypropan-2-yl)-5,12-dimethyl-4-oxatricyclo[10.3.0.0³,⁵]pentadec-9-en-9-yl]methoxy}-3-hydroxy-3-methyl-5-oxopentanoic acid)

3D-SDF for NP0210088 (5-{[6,11-dihydroxy-15-(2-hydroxypropan-2-yl)-5,12-dimethyl-4-oxatricyclo[10.3.0.0³,⁵]pentadec-9-en-9-yl]methoxy}-3-hydroxy-3-methyl-5-oxopentanoic acid)

PDB for NP0210088 (5-{[6,11-dihydroxy-15-(2-hydroxypropan-2-yl)-5,12-dimethyl-4-oxatricyclo[10.3.0.0³,⁵]pentadec-9-en-9-yl]methoxy}-3-hydroxy-3-methyl-5-oxopentanoic acid)

3D PDB for NP0210088 (5-{[6,11-dihydroxy-15-(2-hydroxypropan-2-yl)-5,12-dimethyl-4-oxatricyclo[10.3.0.0³,⁵]pentadec-9-en-9-yl]methoxy}-3-hydroxy-3-methyl-5-oxopentanoic acid)

SMILES for NP0210088 (5-{[6,11-dihydroxy-15-(2-hydroxypropan-2-yl)-5,12-dimethyl-4-oxatricyclo[10.3.0.0³,⁵]pentadec-9-en-9-yl]methoxy}-3-hydroxy-3-methyl-5-oxopentanoic acid)

INCHI for NP0210088 (5-{[6,11-dihydroxy-15-(2-hydroxypropan-2-yl)-5,12-dimethyl-4-oxatricyclo[10.3.0.0³,⁵]pentadec-9-en-9-yl]methoxy}-3-hydroxy-3-methyl-5-oxopentanoic acid)

Structure for NP0210088 (5-{[6,11-dihydroxy-15-(2-hydroxypropan-2-yl)-5,12-dimethyl-4-oxatricyclo[10.3.0.0³,⁵]pentadec-9-en-9-yl]methoxy}-3-hydroxy-3-methyl-5-oxopentanoic acid)

3D Structure for NP0210088 (5-{[6,11-dihydroxy-15-(2-hydroxypropan-2-yl)-5,12-dimethyl-4-oxatricyclo[10.3.0.0³,⁵]pentadec-9-en-9-yl]methoxy}-3-hydroxy-3-methyl-5-oxopentanoic acid)