NP-MRD: Showing NP-Card for (1r,3s,4r,6s,7s,8s,10r,13s,14s,16s)-3,4,6,7,14-pentahydroxy-5,5,14-trimethyl-9-methylidenetetracyclo[11.2.1.0¹,¹⁰.0⁴,⁸]hexadecan-16-yl (2r,3s)-3-hydroxy-2-methylbutanoate (NP0252097)

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Record Information

Version

2.0

Created at

2022-09-07 15:29:59 UTC

Updated at

2022-09-07 15:29:59 UTC

NP-MRD ID

NP0252097

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1r,3s,4r,6s,7s,8s,10r,13s,14s,16s)-3,4,6,7,14-pentahydroxy-5,5,14-trimethyl-9-methylidenetetracyclo[11.2.1.0¹,¹⁰.0⁴,⁸]hexadecan-16-yl (2r,3s)-3-hydroxy-2-methylbutanoate

Description

(1R,3S,4R,6S,7S,8S,10R,13S,14S,16S)-3,4,6,7,14-pentahydroxy-5,5,14-trimethyl-9-methylidenetetracyclo[11.2.1.0¹,¹⁰.0⁴,⁸]Hexadecan-16-yl (2R,3S)-3-hydroxy-2-methylbutanoate belongs to the class of organic compounds known as beta hydroxy acids and derivatives. Beta hydroxy acids and derivatives are compounds containing a carboxylic acid substituted with a hydroxyl group on the C3 carbon atom. Based on a literature review very few articles have been published on (1R,3S,4R,6S,7S,8S,10R,13S,14S,16S)-3,4,6,7,14-pentahydroxy-5,5,14-trimethyl-9-methylidenetetracyclo[11.2.1.0¹,¹⁰.0⁴,⁸]Hexadecan-16-yl (2R,3S)-3-hydroxy-2-methylbutanoate.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309072217302D          

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M  END

     RDKit          3D

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M  END


  Mrv1652309072217302D          

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 22 23  1  0  0  0  0
 24 23  1  1  0  0  0
  2 24  1  0  0  0  0
 16 24  1  0  0  0  0
 21 25  1  0  0  0  0
 16 25  1  0  0  0  0
 25 26  1  1  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  6  0  0  0
 29 31  1  0  0  0  0
 31 32  1  0  0  0  0
 31 33  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0252097

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@H](O)[C@@H](C)C(=O)O[C@H]1[C@@H]2CC[C@@H]3C(=C)[C@H]4[C@H](O)[C@@H](O)C(C)(C)[C@@]4(O)[C@@H](O)C[C@]13C[C@]2(C)O

> <INCHI_IDENTIFIER>
InChI=1S/C25H40O8/c1-11(13(3)26)21(30)33-20-15-8-7-14-12(2)17-18(28)19(29)22(4,5)25(17,32)16(27)9-24(14,20)10-23(15,6)31/h11,13-20,26-29,31-32H,2,7-10H2,1,3-6H3/t11-,13+,14-,15+,16+,17+,18+,19-,20+,23+,24-,25-/m1/s1

> <INCHI_KEY>
WZAGICLCYMETRE-UBVJWZBESA-N

> <FORMULA>
C25H40O8

> <MOLECULAR_WEIGHT>
468.587

> <EXACT_MASS>
468.272318248

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
73

> <JCHEM_AVERAGE_POLARIZABILITY>
49.292948613693284

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
6

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1R,3S,4R,6S,7S,8S,10R,13S,14S,16S)-3,4,6,7,14-pentahydroxy-5,5,14-trimethyl-9-methylidenetetracyclo[11.2.1.0^{1,10}.0^{4,8}]hexadecan-16-yl (2R,3S)-3-hydroxy-2-methylbutanoate

> <JCHEM_LOGP>
-0.5013076086666665

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.584218514920508

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.874843139955033

> <JCHEM_PKA_STRONGEST_BASIC>
-2.7867801050808056

> <JCHEM_POLAR_SURFACE_AREA>
147.68

> <JCHEM_REFRACTIVITY>
118.9559

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(1R,3S,4R,6S,7S,8S,10R,13S,14S,16S)-3,4,6,7,14-pentahydroxy-5,5,14-trimethyl-9-methylidenetetracyclo[11.2.1.0^{1,10}.0^{4,8}]hexadecan-16-yl (2R,3S)-3-hydroxy-2-methylbutanoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 07-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   07-SEP-22         0                                  
HETATM    1  C   UNK     0       7.475  -3.508   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       6.740  -2.071   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       7.963  -1.122   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       9.421  -1.619   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0      10.102  -3.067   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0      10.344  -0.387   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      11.930  -0.663   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       9.458   0.872   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      11.009   1.463   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       9.653   2.461   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       7.986   0.418   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       8.482   2.059   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       6.809   1.432   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       6.500   3.002   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       5.295   1.125   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       4.483  -0.237   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       3.182   0.824   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       1.750   0.049   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       0.869   1.415   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       0.196  -0.404   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       2.080  -1.531   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       2.784  -2.988   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       4.375  -3.117   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       5.221  -1.715   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       3.339  -0.943   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0       3.769  -2.467   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0       3.532  -4.248   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0       2.138  -3.595   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0       3.674  -5.905   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       5.210  -6.020   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       2.766  -7.237   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       3.434  -8.624   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0       1.230  -7.122   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   24                                                  
CONECT    3    2    4   11                                                  
CONECT    4    3    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9   10   11                                             
CONECT    9    8                                                            
CONECT   10    8                                                            
CONECT   11    8    3   12   13                                             
CONECT   12   11                                                            
CONECT   13   11   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13   16                                                       
CONECT   16   15   17   24   25                                             
CONECT   17   16   18                                                       
CONECT   18   17   19   20   21                                             
CONECT   19   18                                                            
CONECT   20   18                                                            
CONECT   21   18   22   25                                                  
CONECT   22   21   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23    2   16                                                  
CONECT   25   21   16   26                                                  
CONECT   26   25   27                                                       
CONECT   27   26   28   29                                                  
CONECT   28   27                                                            
CONECT   29   27   30   31                                                  
CONECT   30   29                                                            
CONECT   31   29   32   33                                                  
CONECT   32   31                                                            
CONECT   33   31                                                            
MASTER        0    0    0    0    0    0    0    0   33    0   72    0
END

View in JSmol

Synonyms

Value	Source
(1R,3S,4R,6S,7S,8S,10R,13S,14S,16S)-3,4,6,7,14-Pentahydroxy-5,5,14-trimethyl-9-methylidenetetracyclo[11.2.1.0,.0,]hexadecan-16-yl (2R,3S)-3-hydroxy-2-methylbutanoic acid	Generator

Chemical Formula

C₂₅H₄₀O₈

Average Mass

468.5870 Da

Monoisotopic Mass

468.27232 Da

IUPAC Name

(1R,3S,4R,6S,7S,8S,10R,13S,14S,16S)-3,4,6,7,14-pentahydroxy-5,5,14-trimethyl-9-methylidenetetracyclo[11.2.1.0^{1,10}.0^{4,8}]hexadecan-16-yl (2R,3S)-3-hydroxy-2-methylbutanoate

Traditional Name

(1R,3S,4R,6S,7S,8S,10R,13S,14S,16S)-3,4,6,7,14-pentahydroxy-5,5,14-trimethyl-9-methylidenetetracyclo[11.2.1.0^{1,10}.0^{4,8}]hexadecan-16-yl (2R,3S)-3-hydroxy-2-methylbutanoate

CAS Registry Number

Not Available

SMILES

C[C@H](O)[C@@H](C)C(=O)O[C@H]1[C@@H]2CC[C@@H]3C(=C)[C@H]4[C@H](O)[C@@H](O)C(C)(C)[C@@]4(O)[C@@H](O)C[C@]13C[C@]2(C)O

InChI Identifier

InChI=1S/C25H40O8/c1-11(13(3)26)21(30)33-20-15-8-7-14-12(2)17-18(28)19(29)22(4,5)25(17,32)16(27)9-24(14,20)10-23(15,6)31/h11,13-20,26-29,31-32H,2,7-10H2,1,3-6H3/t11-,13+,14-,15+,16+,17+,18+,19-,20+,23+,24-,25-/m1/s1

InChI Key

WZAGICLCYMETRE-UBVJWZBESA-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 beta hydroxy acids and derivatives. Beta hydroxy acids and derivatives are compounds containing a carboxylic acid substituted with a hydroxyl group on the C3 carbon atom.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Hydroxy acids and derivatives

Sub Class

Beta hydroxy acids and derivatives

Direct Parent

Beta hydroxy acids and derivatives

Alternative Parents

Substituents

Beta-hydroxy acid
Fatty acid ester
Fatty acyl
Cyclic alcohol
Tertiary alcohol
Carboxylic acid ester
Secondary alcohol
Carboxylic acid derivative
Polyol
Monocarboxylic acid or derivatives
Hydrocarbon derivative
Organic oxide
Alcohol
Carbonyl group
Organic oxygen compound
Organooxygen compound
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic 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	-0.5	ChemAxon
pKa (Strongest Acidic)	12.87	ChemAxon
pKa (Strongest Basic)	-2.8	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	147.68 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	118.96 m³·mol⁻¹	ChemAxon
Polarizability	49.29 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	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

162893308

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (1r,3s,4r,6s,7s,8s,10r,13s,14s,16s)-3,4,6,7,14-pentahydroxy-5,5,14-trimethyl-9-methylidenetetracyclo[11.2.1.0¹,¹⁰.0⁴,⁸]hexadecan-16-yl (2r,3s)-3-hydroxy-2-methylbutanoate (NP0252097)

MOL for NP0252097 ((1r,3s,4r,6s,7s,8s,10r,13s,14s,16s)-3,4,6,7,14-pentahydroxy-5,5,14-trimethyl-9-methylidenetetracyclo[11.2.1.0¹,¹⁰.0⁴,⁸]hexadecan-16-yl (2r,3s)-3-hydroxy-2-methylbutanoate)

3D MOL for NP0252097 ((1r,3s,4r,6s,7s,8s,10r,13s,14s,16s)-3,4,6,7,14-pentahydroxy-5,5,14-trimethyl-9-methylidenetetracyclo[11.2.1.0¹,¹⁰.0⁴,⁸]hexadecan-16-yl (2r,3s)-3-hydroxy-2-methylbutanoate)

3D SDF for NP0252097 ((1r,3s,4r,6s,7s,8s,10r,13s,14s,16s)-3,4,6,7,14-pentahydroxy-5,5,14-trimethyl-9-methylidenetetracyclo[11.2.1.0¹,¹⁰.0⁴,⁸]hexadecan-16-yl (2r,3s)-3-hydroxy-2-methylbutanoate)

3D-SDF for NP0252097 ((1r,3s,4r,6s,7s,8s,10r,13s,14s,16s)-3,4,6,7,14-pentahydroxy-5,5,14-trimethyl-9-methylidenetetracyclo[11.2.1.0¹,¹⁰.0⁴,⁸]hexadecan-16-yl (2r,3s)-3-hydroxy-2-methylbutanoate)

PDB for NP0252097 ((1r,3s,4r,6s,7s,8s,10r,13s,14s,16s)-3,4,6,7,14-pentahydroxy-5,5,14-trimethyl-9-methylidenetetracyclo[11.2.1.0¹,¹⁰.0⁴,⁸]hexadecan-16-yl (2r,3s)-3-hydroxy-2-methylbutanoate)

3D PDB for NP0252097 ((1r,3s,4r,6s,7s,8s,10r,13s,14s,16s)-3,4,6,7,14-pentahydroxy-5,5,14-trimethyl-9-methylidenetetracyclo[11.2.1.0¹,¹⁰.0⁴,⁸]hexadecan-16-yl (2r,3s)-3-hydroxy-2-methylbutanoate)

SMILES for NP0252097 ((1r,3s,4r,6s,7s,8s,10r,13s,14s,16s)-3,4,6,7,14-pentahydroxy-5,5,14-trimethyl-9-methylidenetetracyclo[11.2.1.0¹,¹⁰.0⁴,⁸]hexadecan-16-yl (2r,3s)-3-hydroxy-2-methylbutanoate)

INCHI for NP0252097 ((1r,3s,4r,6s,7s,8s,10r,13s,14s,16s)-3,4,6,7,14-pentahydroxy-5,5,14-trimethyl-9-methylidenetetracyclo[11.2.1.0¹,¹⁰.0⁴,⁸]hexadecan-16-yl (2r,3s)-3-hydroxy-2-methylbutanoate)

Structure for NP0252097 ((1r,3s,4r,6s,7s,8s,10r,13s,14s,16s)-3,4,6,7,14-pentahydroxy-5,5,14-trimethyl-9-methylidenetetracyclo[11.2.1.0¹,¹⁰.0⁴,⁸]hexadecan-16-yl (2r,3s)-3-hydroxy-2-methylbutanoate)

3D Structure for NP0252097 ((1r,3s,4r,6s,7s,8s,10r,13s,14s,16s)-3,4,6,7,14-pentahydroxy-5,5,14-trimethyl-9-methylidenetetracyclo[11.2.1.0¹,¹⁰.0⁴,⁸]hexadecan-16-yl (2r,3s)-3-hydroxy-2-methylbutanoate)