NP-MRD: Showing NP-Card for 8-hydroxy-5-[(3-hydroxy-3-methylbutanoyl)oxy]-10-methyl-11-oxo-4,12-dioxapentacyclo[7.7.0.0¹,⁶.0²,¹³.0¹⁰,¹⁵]hexadec-2-en-14-yl 3-(acetyloxy)-2-methylbutanoate (NP0149147)

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Record Information

Version

2.0

Created at

2022-09-02 04:59:44 UTC

Updated at

2022-09-02 04:59:45 UTC

NP-MRD ID

NP0149147

Secondary Accession Numbers

None

Natural Product Identification

Common Name

8-hydroxy-5-[(3-hydroxy-3-methylbutanoyl)oxy]-10-methyl-11-oxo-4,12-dioxapentacyclo[7.7.0.0¹,⁶.0²,¹³.0¹⁰,¹⁵]hexadec-2-en-14-yl 3-(acetyloxy)-2-methylbutanoate

Description

8-Hydroxy-5-[(3-hydroxy-3-methylbutanoyl)oxy]-10-methyl-11-oxo-4,12-dioxapentacyclo[7.7.0.0¹,⁶.0²,¹³.0¹⁰,¹⁵]Hexadec-2-en-14-yl 3-(acetyloxy)-2-methylbutanoate belongs to the class of organic compounds known as tetracarboxylic acids and derivatives. These are carboxylic acids containing exactly four carboxyl groups. Based on a literature review very few articles have been published on 8-hydroxy-5-[(3-hydroxy-3-methylbutanoyl)oxy]-10-methyl-11-oxo-4,12-dioxapentacyclo[7.7.0.0¹,⁶.0²,¹³.0¹⁰,¹⁵]Hexadec-2-en-14-yl 3-(acetyloxy)-2-methylbutanoate.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309022206592D          

 38 42  0  0  0  0            999 V2000
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M  END

     RDKit          3D

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M  END


  Mrv1652309022206592D          

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    1.9911    0.8082    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8421   -2.6087    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2597   -3.3647    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7297   -4.0046    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9040   -4.8110    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9900   -3.6443    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
  5  7  1  0  0  0  0
  7  8  1  0  0  0  0
  7  9  1  0  0  0  0
  9 10  2  0  0  0  0
  9 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  2  0  0  0  0
 15 17  1  0  0  0  0
 17 18  1  0  0  0  0
 17 19  1  0  0  0  0
 12 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 13 22  1  0  0  0  0
 22 23  2  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  2  0  0  0  0
 27 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
 30 32  1  0  0  0  0
 30 33  1  0  0  0  0
 25 34  1  0  0  0  0
 21 34  1  0  0  0  0
 34 35  1  0  0  0  0
 35 36  1  0  0  0  0
 36 37  1  0  0  0  0
 36 38  1  0  0  0  0
 17 38  1  0  0  0  0
 21 38  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0149147

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(OC(C)=O)C(C)C(=O)OC1C2CC34C5CC(O)C3C2(C)C(=O)OC1C4=COC5OC(=O)CC(C)(C)O

> <INCHI_IDENTIFIER>
InChI=1S/C27H36O11/c1-11(12(2)35-13(3)28)22(31)37-19-15-8-27-14-7-17(29)21(27)26(15,6)24(32)38-20(19)16(27)10-34-23(14)36-18(30)9-25(4,5)33/h10-12,14-15,17,19-21,23,29,33H,7-9H2,1-6H3

> <INCHI_KEY>
VTJDQCOBISUPSR-UHFFFAOYSA-N

> <FORMULA>
C27H36O11

> <MOLECULAR_WEIGHT>
536.574

> <EXACT_MASS>
536.225761979

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
74

> <JCHEM_AVERAGE_POLARIZABILITY>
54.59652963192333

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
8-hydroxy-5-[(3-hydroxy-3-methylbutanoyl)oxy]-10-methyl-11-oxo-4,12-dioxapentacyclo[7.7.0.0^{1,6}.0^{2,13}.0^{10,15}]hexadec-2-en-14-yl 3-(acetyloxy)-2-methylbutanoate

> <ALOGPS_LOGP>
1.65

> <JCHEM_LOGP>
0.502040872666668

> <ALOGPS_LOGS>
-3.03

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
15.317589361653145

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.67542553621696

> <JCHEM_PKA_STRONGEST_BASIC>
-2.7421574355175116

> <JCHEM_POLAR_SURFACE_AREA>
154.89

> <JCHEM_REFRACTIVITY>
126.9518

> <JCHEM_ROTATABLE_BOND_COUNT>
10

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
4.97e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
8-hydroxy-5-[(3-hydroxy-3-methylbutanoyl)oxy]-10-methyl-11-oxo-4,12-dioxapentacyclo[7.7.0.0^{1,6}.0^{2,13}.0^{10,15}]hexadec-2-en-14-yl 3-(acetyloxy)-2-methylbutanoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 02-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   02-SEP-22         0                                  
HETATM    1  C   UNK     0      -8.767  -2.387   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -7.433  -1.617   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0      -7.433  -0.077   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0      -6.099  -2.387   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0      -4.766  -1.617   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -4.766  -0.077   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -3.432  -2.387   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -3.432  -3.927   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -2.098  -1.617   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0      -2.098  -0.077   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0      -0.765  -2.387   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0      -0.765  -3.927   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -1.317  -4.780   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0      -2.221  -6.254   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0      -1.164  -7.411   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      -1.554  -8.901   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       0.318  -6.923   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       0.621  -8.433   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       0.208  -5.430   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       1.476  -4.193   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       1.944  -5.149   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       0.536  -3.690   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       1.291  -2.362   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       2.820  -2.158   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       3.821  -3.360   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0       5.322  -3.019   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0       5.778  -1.548   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0       7.280  -1.207   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0       4.732  -0.418   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       5.188   1.053   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       5.643   2.524   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       6.659   0.597   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0       3.717   1.509   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0       3.439  -4.870   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       4.218  -6.281   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0       3.229  -7.475   0.000  0.00  0.00           C+0
HETATM   37  O   UNK     0       3.554  -8.980   0.000  0.00  0.00           O+0
HETATM   38  C   UNK     0       1.848  -6.803   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12                                                       
CONECT   12   11   13   19                                                  
CONECT   13   12   14   22                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15   18   19   38                                             
CONECT   18   17                                                            
CONECT   19   17   12   20                                                  
CONECT   20   19   21                                                       
CONECT   21   20   22   34   38                                             
CONECT   22   21   13   23                                                  
CONECT   23   22   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24   26   34                                                  
CONECT   26   25   27                                                       
CONECT   27   26   28   29                                                  
CONECT   28   27                                                            
CONECT   29   27   30                                                       
CONECT   30   29   31   32   33                                             
CONECT   31   30                                                            
CONECT   32   30                                                            
CONECT   33   30                                                            
CONECT   34   25   21   35                                                  
CONECT   35   34   36                                                       
CONECT   36   35   37   38                                                  
CONECT   37   36                                                            
CONECT   38   36   17   21                                                  
MASTER        0    0    0    0    0    0    0    0   38    0   84    0
END

View in JSmol

Synonyms

Value	Source
8-Hydroxy-5-[(3-hydroxy-3-methylbutanoyl)oxy]-10-methyl-11-oxo-4,12-dioxapentacyclo[7.7.0.0,.0,.0,]hexadec-2-en-14-yl 3-(acetyloxy)-2-methylbutanoic acid	Generator

Chemical Formula

C₂₇H₃₆O₁₁

Average Mass

536.5740 Da

Monoisotopic Mass

536.22576 Da

IUPAC Name

8-hydroxy-5-[(3-hydroxy-3-methylbutanoyl)oxy]-10-methyl-11-oxo-4,12-dioxapentacyclo[7.7.0.0^{1,6}.0^{2,13}.0^{10,15}]hexadec-2-en-14-yl 3-(acetyloxy)-2-methylbutanoate

Traditional Name

8-hydroxy-5-[(3-hydroxy-3-methylbutanoyl)oxy]-10-methyl-11-oxo-4,12-dioxapentacyclo[7.7.0.0^{1,6}.0^{2,13}.0^{10,15}]hexadec-2-en-14-yl 3-(acetyloxy)-2-methylbutanoate

CAS Registry Number

Not Available

SMILES

CC(OC(C)=O)C(C)C(=O)OC1C2CC34C5CC(O)C3C2(C)C(=O)OC1C4=COC5OC(=O)CC(C)(C)O

InChI Identifier

InChI=1S/C27H36O11/c1-11(12(2)35-13(3)28)22(31)37-19-15-8-27-14-7-17(29)21(27)26(15,6)24(32)38-20(19)16(27)10-34-23(14)36-18(30)9-25(4,5)33/h10-12,14-15,17,19-21,23,29,33H,7-9H2,1-6H3

InChI Key

VTJDQCOBISUPSR-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 tetracarboxylic acids and derivatives. These are carboxylic acids containing exactly four carboxyl groups.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Tetracarboxylic acids and derivatives

Direct Parent

Tetracarboxylic acids and derivatives

Alternative Parents

Substituents

Tetracarboxylic acid or derivatives
Caprolactone
Delta valerolactone
Fatty acid ester
Delta_valerolactone
Oxepane
Fatty acyl
Oxane
Cyclic alcohol
Tertiary alcohol
Carboxylic acid ester
Lactone
Secondary alcohol
Organoheterocyclic compound
Oxacycle
Acetal
Hydrocarbon derivative
Organic oxide
Carbonyl group
Organic oxygen compound
Alcohol
Organooxygen compound
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	1.65	ALOGPS
logP	0.5	ChemAxon
logS	-3	ALOGPS
pKa (Strongest Acidic)	14.68	ChemAxon
pKa (Strongest Basic)	-2.7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	154.89 Å²	ChemAxon
Rotatable Bond Count	10	ChemAxon
Refractivity	126.95 m³·mol⁻¹	ChemAxon
Polarizability	54.6 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	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

14355451

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 8-hydroxy-5-[(3-hydroxy-3-methylbutanoyl)oxy]-10-methyl-11-oxo-4,12-dioxapentacyclo[7.7.0.0¹,⁶.0²,¹³.0¹⁰,¹⁵]hexadec-2-en-14-yl 3-(acetyloxy)-2-methylbutanoate (NP0149147)

MOL for NP0149147 (8-hydroxy-5-[(3-hydroxy-3-methylbutanoyl)oxy]-10-methyl-11-oxo-4,12-dioxapentacyclo[7.7.0.0¹,⁶.0²,¹³.0¹⁰,¹⁵]hexadec-2-en-14-yl 3-(acetyloxy)-2-methylbutanoate)

3D MOL for NP0149147 (8-hydroxy-5-[(3-hydroxy-3-methylbutanoyl)oxy]-10-methyl-11-oxo-4,12-dioxapentacyclo[7.7.0.0¹,⁶.0²,¹³.0¹⁰,¹⁵]hexadec-2-en-14-yl 3-(acetyloxy)-2-methylbutanoate)

3D SDF for NP0149147 (8-hydroxy-5-[(3-hydroxy-3-methylbutanoyl)oxy]-10-methyl-11-oxo-4,12-dioxapentacyclo[7.7.0.0¹,⁶.0²,¹³.0¹⁰,¹⁵]hexadec-2-en-14-yl 3-(acetyloxy)-2-methylbutanoate)

3D-SDF for NP0149147 (8-hydroxy-5-[(3-hydroxy-3-methylbutanoyl)oxy]-10-methyl-11-oxo-4,12-dioxapentacyclo[7.7.0.0¹,⁶.0²,¹³.0¹⁰,¹⁵]hexadec-2-en-14-yl 3-(acetyloxy)-2-methylbutanoate)

PDB for NP0149147 (8-hydroxy-5-[(3-hydroxy-3-methylbutanoyl)oxy]-10-methyl-11-oxo-4,12-dioxapentacyclo[7.7.0.0¹,⁶.0²,¹³.0¹⁰,¹⁵]hexadec-2-en-14-yl 3-(acetyloxy)-2-methylbutanoate)

3D PDB for NP0149147 (8-hydroxy-5-[(3-hydroxy-3-methylbutanoyl)oxy]-10-methyl-11-oxo-4,12-dioxapentacyclo[7.7.0.0¹,⁶.0²,¹³.0¹⁰,¹⁵]hexadec-2-en-14-yl 3-(acetyloxy)-2-methylbutanoate)

SMILES for NP0149147 (8-hydroxy-5-[(3-hydroxy-3-methylbutanoyl)oxy]-10-methyl-11-oxo-4,12-dioxapentacyclo[7.7.0.0¹,⁶.0²,¹³.0¹⁰,¹⁵]hexadec-2-en-14-yl 3-(acetyloxy)-2-methylbutanoate)

INCHI for NP0149147 (8-hydroxy-5-[(3-hydroxy-3-methylbutanoyl)oxy]-10-methyl-11-oxo-4,12-dioxapentacyclo[7.7.0.0¹,⁶.0²,¹³.0¹⁰,¹⁵]hexadec-2-en-14-yl 3-(acetyloxy)-2-methylbutanoate)

Structure for NP0149147 (8-hydroxy-5-[(3-hydroxy-3-methylbutanoyl)oxy]-10-methyl-11-oxo-4,12-dioxapentacyclo[7.7.0.0¹,⁶.0²,¹³.0¹⁰,¹⁵]hexadec-2-en-14-yl 3-(acetyloxy)-2-methylbutanoate)

3D Structure for NP0149147 (8-hydroxy-5-[(3-hydroxy-3-methylbutanoyl)oxy]-10-methyl-11-oxo-4,12-dioxapentacyclo[7.7.0.0¹,⁶.0²,¹³.0¹⁰,¹⁵]hexadec-2-en-14-yl 3-(acetyloxy)-2-methylbutanoate)