NP-MRD: Showing NP-Card for (1r,5r,6s,8s,9s,10s,13s,14r,15s)-8-hydroxy-10-methyl-14-{[(2r)-2-methylbutanoyl]oxy}-11-oxo-4,12-dioxapentacyclo[7.7.0.0¹,⁶.0²,¹³.0¹⁰,¹⁵]hexadec-2-en-5-yl 3-hydroxy-3-methylbutanoate (NP0146777)

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Record Information

Version

2.0

Created at

2022-09-02 02:14:39 UTC

Updated at

2022-09-02 02:14:39 UTC

NP-MRD ID

NP0146777

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1r,5r,6s,8s,9s,10s,13s,14r,15s)-8-hydroxy-10-methyl-14-{[(2r)-2-methylbutanoyl]oxy}-11-oxo-4,12-dioxapentacyclo[7.7.0.0¹,⁶.0²,¹³.0¹⁰,¹⁵]hexadec-2-en-5-yl 3-hydroxy-3-methylbutanoate

Description

(1R,5R,6S,8S,9S,10S,13S,14R,15S)-8-hydroxy-10-methyl-14-{[(2R)-2-methylbutanoyl]oxy}-11-oxo-4,12-dioxapentacyclo[7.7.0.0¹,⁶.0²,¹³.0¹⁰,¹⁵]Hexadec-2-en-5-yl 3-hydroxy-3-methylbutanoate belongs to the class of organic compounds known as tricarboxylic acids and derivatives. These are carboxylic acids containing exactly three carboxyl groups. Based on a literature review very few articles have been published on (1R,5R,6S,8S,9S,10S,13S,14R,15S)-8-hydroxy-10-methyl-14-{[(2R)-2-methylbutanoyl]oxy}-11-oxo-4,12-dioxapentacyclo[7.7.0.0¹,⁶.0²,¹³.0¹⁰,¹⁵]Hexadec-2-en-5-yl 3-hydroxy-3-methylbutanoate.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309022204142D          

 34 38  0  0  1  0            999 V2000
    3.4349   -1.3476    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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M  END

     RDKit          3D

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M  END


  Mrv1652309022204142D          

 34 38  0  0  1  0            999 V2000
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 31 32  1  0  0  0  0
 32 33  1  6  0  0  0
 34 32  1  6  0  0  0
 13 34  1  0  0  0  0
 17 34  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0146777

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC[C@@H](C)C(=O)O[C@@H]1[C@H]2C[C@]34[C@@H]5C[C@H](O)[C@@H]3[C@@]2(C)C(=O)O[C@H]1C4=CO[C@@H]5OC(=O)CC(C)(C)O

> <INCHI_IDENTIFIER>
InChI=1S/C25H34O9/c1-6-11(2)20(28)33-17-13-8-25-12-7-15(26)19(25)24(13,5)22(29)34-18(17)14(25)10-31-21(12)32-16(27)9-23(3,4)30/h10-13,15,17-19,21,26,30H,6-9H2,1-5H3/t11-,12-,13-,15+,17-,18+,19-,21-,24+,25-/m1/s1

> <INCHI_KEY>
TXXCACYWKVHYIQ-ATLYNYPZSA-N

> <FORMULA>
C25H34O9

> <MOLECULAR_WEIGHT>
478.538

> <EXACT_MASS>
478.220282675

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
68

> <JCHEM_AVERAGE_POLARIZABILITY>
48.84849172425425

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1R,5R,6S,8S,9S,10S,13S,14R,15S)-8-hydroxy-10-methyl-14-{[(2R)-2-methylbutanoyl]oxy}-11-oxo-4,12-dioxapentacyclo[7.7.0.0^{1,6}.0^{2,13}.0^{10,15}]hexadec-2-en-5-yl 3-hydroxy-3-methylbutanoate

> <ALOGPS_LOGP>
1.65

> <JCHEM_LOGP>
1.369680259333332

> <ALOGPS_LOGS>
-2.99

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
15.317589361653173

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.675425536217002

> <JCHEM_PKA_STRONGEST_BASIC>
-2.7421574355175116

> <JCHEM_POLAR_SURFACE_AREA>
128.59

> <JCHEM_REFRACTIVITY>
116.2078

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.86e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1R,5R,6S,8S,9S,10S,13S,14R,15S)-8-hydroxy-10-methyl-14-{[(2R)-2-methylbutanoyl]oxy}-11-oxo-4,12-dioxapentacyclo[7.7.0.0^{1,6}.0^{2,13}.0^{10,15}]hexadec-2-en-5-yl 3-hydroxy-3-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       6.412  -2.515   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       4.878  -2.382   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       4.226  -0.987   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       5.108   0.275   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.692  -0.854   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       1.809  -2.116   0.000  0.00  0.00           O+0
HETATM    7  O   UNK     0       2.040   0.541   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       2.922   1.803   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       3.864   2.187   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       5.449   2.876   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       5.246   4.430   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       6.420   5.428   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       3.752   4.880   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.368   6.291   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       2.986   3.593   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       1.238   3.305   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       1.403   4.357   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       1.721   2.355   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       0.341   1.699   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0      -1.029   2.408   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0      -1.160   3.966   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0      -2.586   4.548   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0      -3.803   3.603   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0      -5.229   4.184   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0      -3.593   2.077   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      -4.809   1.133   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      -6.026   0.188   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      -5.754   2.349   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0      -3.865  -0.083   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0       0.018   4.985   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       0.187   6.588   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       1.683   7.000   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0       2.278   8.420   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0       2.429   5.657   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8                                                       
CONECT    8    7    9   15                                                  
CONECT    9    8   10   18                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14   15   34                                             
CONECT   14   13                                                            
CONECT   15   13    8   16                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18   30   34                                             
CONECT   18   17    9   19                                                  
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22   30                                                  
CONECT   22   21   23                                                       
CONECT   23   22   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23   26                                                       
CONECT   26   25   27   28   29                                             
CONECT   27   26                                                            
CONECT   28   26                                                            
CONECT   29   26                                                            
CONECT   30   21   17   31                                                  
CONECT   31   30   32                                                       
CONECT   32   31   33   34                                                  
CONECT   33   32                                                            
CONECT   34   32   13   17                                                  
MASTER        0    0    0    0    0    0    0    0   34    0   76    0
END

View in JSmol

Synonyms

Value	Source
(1R,5R,6S,8S,9S,10S,13S,14R,15S)-8-Hydroxy-10-methyl-14-{[(2R)-2-methylbutanoyl]oxy}-11-oxo-4,12-dioxapentacyclo[7.7.0.0,.0,.0,]hexadec-2-en-5-yl 3-hydroxy-3-methylbutanoic acid	Generator

Chemical Formula

C₂₅H₃₄O₉

Average Mass

478.5380 Da

Monoisotopic Mass

478.22028 Da

IUPAC Name

(1R,5R,6S,8S,9S,10S,13S,14R,15S)-8-hydroxy-10-methyl-14-{[(2R)-2-methylbutanoyl]oxy}-11-oxo-4,12-dioxapentacyclo[7.7.0.0^{1,6}.0^{2,13}.0^{10,15}]hexadec-2-en-5-yl 3-hydroxy-3-methylbutanoate

Traditional Name

(1R,5R,6S,8S,9S,10S,13S,14R,15S)-8-hydroxy-10-methyl-14-{[(2R)-2-methylbutanoyl]oxy}-11-oxo-4,12-dioxapentacyclo[7.7.0.0^{1,6}.0^{2,13}.0^{10,15}]hexadec-2-en-5-yl 3-hydroxy-3-methylbutanoate

CAS Registry Number

Not Available

SMILES

CC[C@@H](C)C(=O)O[C@@H]1[C@H]2C[C@]34[C@@H]5C[C@H](O)[C@@H]3[C@@]2(C)C(=O)O[C@H]1C4=CO[C@@H]5OC(=O)CC(C)(C)O

InChI Identifier

InChI=1S/C25H34O9/c1-6-11(2)20(28)33-17-13-8-25-12-7-15(26)19(25)24(13,5)22(29)34-18(17)14(25)10-31-21(12)32-16(27)9-23(3,4)30/h10-13,15,17-19,21,26,30H,6-9H2,1-5H3/t11-,12-,13-,15+,17-,18+,19-,21-,24+,25-/m1/s1

InChI Key

TXXCACYWKVHYIQ-ATLYNYPZSA-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 tricarboxylic acids and derivatives. These are carboxylic acids containing exactly three carboxyl groups.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Tricarboxylic acids and derivatives

Direct Parent

Tricarboxylic acids and derivatives

Alternative Parents

Substituents

Tricarboxylic 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	1.37	ChemAxon
logS	-3	ALOGPS
pKa (Strongest Acidic)	14.68	ChemAxon
pKa (Strongest Basic)	-2.7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	128.59 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	116.21 m³·mol⁻¹	ChemAxon
Polarizability	48.85 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	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

163029342

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (1r,5r,6s,8s,9s,10s,13s,14r,15s)-8-hydroxy-10-methyl-14-{[(2r)-2-methylbutanoyl]oxy}-11-oxo-4,12-dioxapentacyclo[7.7.0.0¹,⁶.0²,¹³.0¹⁰,¹⁵]hexadec-2-en-5-yl 3-hydroxy-3-methylbutanoate (NP0146777)

MOL for NP0146777 ((1r,5r,6s,8s,9s,10s,13s,14r,15s)-8-hydroxy-10-methyl-14-{[(2r)-2-methylbutanoyl]oxy}-11-oxo-4,12-dioxapentacyclo[7.7.0.0¹,⁶.0²,¹³.0¹⁰,¹⁵]hexadec-2-en-5-yl 3-hydroxy-3-methylbutanoate)

3D MOL for NP0146777 ((1r,5r,6s,8s,9s,10s,13s,14r,15s)-8-hydroxy-10-methyl-14-{[(2r)-2-methylbutanoyl]oxy}-11-oxo-4,12-dioxapentacyclo[7.7.0.0¹,⁶.0²,¹³.0¹⁰,¹⁵]hexadec-2-en-5-yl 3-hydroxy-3-methylbutanoate)

3D SDF for NP0146777 ((1r,5r,6s,8s,9s,10s,13s,14r,15s)-8-hydroxy-10-methyl-14-{[(2r)-2-methylbutanoyl]oxy}-11-oxo-4,12-dioxapentacyclo[7.7.0.0¹,⁶.0²,¹³.0¹⁰,¹⁵]hexadec-2-en-5-yl 3-hydroxy-3-methylbutanoate)

3D-SDF for NP0146777 ((1r,5r,6s,8s,9s,10s,13s,14r,15s)-8-hydroxy-10-methyl-14-{[(2r)-2-methylbutanoyl]oxy}-11-oxo-4,12-dioxapentacyclo[7.7.0.0¹,⁶.0²,¹³.0¹⁰,¹⁵]hexadec-2-en-5-yl 3-hydroxy-3-methylbutanoate)

PDB for NP0146777 ((1r,5r,6s,8s,9s,10s,13s,14r,15s)-8-hydroxy-10-methyl-14-{[(2r)-2-methylbutanoyl]oxy}-11-oxo-4,12-dioxapentacyclo[7.7.0.0¹,⁶.0²,¹³.0¹⁰,¹⁵]hexadec-2-en-5-yl 3-hydroxy-3-methylbutanoate)

3D PDB for NP0146777 ((1r,5r,6s,8s,9s,10s,13s,14r,15s)-8-hydroxy-10-methyl-14-{[(2r)-2-methylbutanoyl]oxy}-11-oxo-4,12-dioxapentacyclo[7.7.0.0¹,⁶.0²,¹³.0¹⁰,¹⁵]hexadec-2-en-5-yl 3-hydroxy-3-methylbutanoate)

SMILES for NP0146777 ((1r,5r,6s,8s,9s,10s,13s,14r,15s)-8-hydroxy-10-methyl-14-{[(2r)-2-methylbutanoyl]oxy}-11-oxo-4,12-dioxapentacyclo[7.7.0.0¹,⁶.0²,¹³.0¹⁰,¹⁵]hexadec-2-en-5-yl 3-hydroxy-3-methylbutanoate)

INCHI for NP0146777 ((1r,5r,6s,8s,9s,10s,13s,14r,15s)-8-hydroxy-10-methyl-14-{[(2r)-2-methylbutanoyl]oxy}-11-oxo-4,12-dioxapentacyclo[7.7.0.0¹,⁶.0²,¹³.0¹⁰,¹⁵]hexadec-2-en-5-yl 3-hydroxy-3-methylbutanoate)

Structure for NP0146777 ((1r,5r,6s,8s,9s,10s,13s,14r,15s)-8-hydroxy-10-methyl-14-{[(2r)-2-methylbutanoyl]oxy}-11-oxo-4,12-dioxapentacyclo[7.7.0.0¹,⁶.0²,¹³.0¹⁰,¹⁵]hexadec-2-en-5-yl 3-hydroxy-3-methylbutanoate)

3D Structure for NP0146777 ((1r,5r,6s,8s,9s,10s,13s,14r,15s)-8-hydroxy-10-methyl-14-{[(2r)-2-methylbutanoyl]oxy}-11-oxo-4,12-dioxapentacyclo[7.7.0.0¹,⁶.0²,¹³.0¹⁰,¹⁵]hexadec-2-en-5-yl 3-hydroxy-3-methylbutanoate)