NP-MRD: Showing NP-Card for (3s)-5-{[(1r,3as,4s,9r,12as)-4,9-dihydroxy-1-(2-hydroxypropan-2-yl)-3a-methyl-10-methylidene-1h,2h,3h,4h,7h,8h,9h,11h,12h,12ah-cyclopenta[11]annulen-6-yl]methoxy}-3-hydroxy-3-methyl-5-oxopentanoic acid (NP0246380)

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Record Information

Version

2.0

Created at

2022-09-07 07:49:59 UTC

Updated at

2022-09-07 07:49:59 UTC

NP-MRD ID

NP0246380

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(3s)-5-{[(1r,3as,4s,9r,12as)-4,9-dihydroxy-1-(2-hydroxypropan-2-yl)-3a-methyl-10-methylidene-1h,2h,3h,4h,7h,8h,9h,11h,12h,12ah-cyclopenta[11]annulen-6-yl]methoxy}-3-hydroxy-3-methyl-5-oxopentanoic acid

Description

(3S)-5-{[(1R,3aS,4S,9R,12aS)-4,9-dihydroxy-1-(2-hydroxypropan-2-yl)-3a-methyl-10-methylidene-1H,2H,3H,3aH,4H,7H,8H,9H,10H,11H,12H,12aH-cyclopenta[11]annulen-6-yl]methoxy}-3-hydroxy-3-methyl-5-oxopentanoic acid belongs to the class of organic compounds known as diterpenoids. These are terpene compounds formed by four isoprene units. Based on a literature review very few articles have been published on (3S)-5-{[(1R,3aS,4S,9R,12aS)-4,9-dihydroxy-1-(2-hydroxypropan-2-yl)-3a-methyl-10-methylidene-1H,2H,3H,3aH,4H,7H,8H,9H,10H,11H,12H,12aH-cyclopenta[11]annulen-6-yl]methoxy}-3-hydroxy-3-methyl-5-oxopentanoic acid.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309072209502D          

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M  END

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M  END


  Mrv1652309072209502D          

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  6  7  1  6  0  0  0
  7  8  1  0  0  0  0
  7  9  1  0  0  0  0
  7 10  1  0  0  0  0
  6 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
  5 13  1  0  0  0  0
 13 14  1  1  0  0  0
 13 15  1  0  0  0  0
 15 16  1  1  0  0  0
 15 17  1  0  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  2  0  0  0  0
 21 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  6  0  0  0
 24 26  1  6  0  0  0
 24 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  2  0  0  0  0
 28 30  1  0  0  0  0
 18 31  1  0  0  0  0
 31 32  1  0  0  0  0
 32 33  1  0  0  0  0
  2 33  1  0  0  0  0
 33 34  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0246380

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@](O)(CC(O)=O)CC(=O)OC\C1=C/[C@H](O)[C@@]2(C)CC[C@H]([C@@H]2CCC(=C)[C@H](O)CC1)C(C)(C)O

> <INCHI_IDENTIFIER>
InChI=1S/C26H42O8/c1-16-6-8-19-18(24(2,3)32)10-11-26(19,5)21(28)12-17(7-9-20(16)27)15-34-23(31)14-25(4,33)13-22(29)30/h12,18-21,27-28,32-33H,1,6-11,13-15H2,2-5H3,(H,29,30)/b17-12-/t18-,19+,20-,21+,25+,26+/m1/s1

> <INCHI_KEY>
ICNPMMJYCAZGAD-NGBACDEASA-N

> <FORMULA>
C26H42O8

> <MOLECULAR_WEIGHT>
482.614

> <EXACT_MASS>
482.287968312

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
76

> <JCHEM_AVERAGE_POLARIZABILITY>
51.60737814163187

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(3S)-5-{[(1R,3aS,4S,9R,12aS)-4,9-dihydroxy-1-(2-hydroxypropan-2-yl)-3a-methyl-10-methylidene-1H,2H,3H,3aH,4H,7H,8H,9H,10H,11H,12H,12aH-cyclopenta[11]annulen-6-yl]methoxy}-3-hydroxy-3-methyl-5-oxopentanoic acid

> <JCHEM_LOGP>
1.521186245999999

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
14.188775993404374

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.075019326491673

> <JCHEM_PKA_STRONGEST_BASIC>
-0.7183643196665522

> <JCHEM_POLAR_SURFACE_AREA>
144.52

> <JCHEM_REFRACTIVITY>
127.46129999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(3S)-5-{[(1R,3aS,4S,9R,12aS)-4,9-dihydroxy-1-(2-hydroxypropan-2-yl)-3a-methyl-10-methylidene-1H,2H,3H,4H,7H,8H,9H,11H,12H,12aH-cyclopenta[11]annulen-6-yl]methoxy}-3-hydroxy-3-methyl-5-oxopentanoic acid

> <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       8.803  -7.920   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       8.424  -6.428   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       6.942  -6.009   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       6.563  -4.517   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       5.081  -4.098   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       3.778  -4.920   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       3.677  -6.457   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       3.576  -7.993   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.214  -6.558   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       2.141  -6.356   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       2.594  -3.935   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       3.165  -2.505   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.702  -2.606   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.169  -1.161   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       5.805  -1.531   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       5.394  -0.047   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       7.445  -1.918   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       8.827  -1.237   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       9.088   0.281   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0      10.533   0.813   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0      10.794   2.331   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       9.610   3.316   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0      12.238   2.864   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      12.499   4.382   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      14.017   4.121   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0      10.982   4.643   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0      12.760   5.899   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      14.205   6.432   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0      14.466   7.950   0.000  0.00  0.00           O+0
HETATM   30  O   UNK     0      15.389   5.447   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0       9.901  -2.340   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       9.184  -3.703   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       9.527  -5.353   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0      11.000  -5.803   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   33                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6   13                                                  
CONECT    6    5    7   11                                                  
CONECT    7    6    8    9   10                                             
CONECT    8    7                                                            
CONECT    9    7                                                            
CONECT   10    7                                                            
CONECT   11    6   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12    5   14   15                                             
CONECT   14   13                                                            
CONECT   15   13   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15   18                                                       
CONECT   18   17   19   31                                                  
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21   24                                                       
CONECT   24   23   25   26   27                                             
CONECT   25   24                                                            
CONECT   26   24                                                            
CONECT   27   24   28                                                       
CONECT   28   27   29   30                                                  
CONECT   29   28                                                            
CONECT   30   28                                                            
CONECT   31   18   32                                                       
CONECT   32   31   33                                                       
CONECT   33   32    2   34                                                  
CONECT   34   33                                                            
MASTER        0    0    0    0    0    0    0    0   34    0   70    0
END

View in JSmol

Synonyms

Value	Source
(3S)-5-{[(1R,3as,4S,9R,12as)-4,9-dihydroxy-1-(2-hydroxypropan-2-yl)-3a-methyl-10-methylidene-1H,2H,3H,3ah,4H,7H,8H,9H,10H,11H,12H,12ah-cyclopenta[11]annulen-6-yl]methoxy}-3-hydroxy-3-methyl-5-oxopentanoate	Generator

Chemical Formula

C₂₆H₄₂O₈

Average Mass

482.6140 Da

Monoisotopic Mass

482.28797 Da

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

C[C@](O)(CC(O)=O)CC(=O)OC\C1=C/[C@H](O)[C@@]2(C)CC[C@H]([C@@H]2CCC(=C)[C@H](O)CC1)C(C)(C)O

InChI Identifier

InChI=1S/C26H42O8/c1-16-6-8-19-18(24(2,3)32)10-11-26(19,5)21(28)12-17(7-9-20(16)27)15-34-23(31)14-25(4,33)13-22(29)30/h12,18-21,27-28,32-33H,1,6-11,13-15H2,2-5H3,(H,29,30)/b17-12-/t18-,19+,20-,21+,25+,26+/m1/s1

InChI Key

ICNPMMJYCAZGAD-NGBACDEASA-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 diterpenoids. These are terpene compounds formed by four isoprene units.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Diterpenoids

Direct Parent

Diterpenoids

Alternative Parents

Substituents

Diterpenoid
Branched fatty acid
Fatty acid ester
Hydroxy fatty acid
Short-chain hydroxy acid
Methyl-branched fatty acid
Dicarboxylic acid or derivatives
Fatty acyl
Tertiary alcohol
Secondary alcohol
Carboxylic acid ester
Carboxylic acid
Carboxylic acid derivative
Carbonyl group
Organooxygen compound
Alcohol
Organic oxygen compound
Hydrocarbon derivative
Organic oxide
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

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

162951074

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (3s)-5-{[(1r,3as,4s,9r,12as)-4,9-dihydroxy-1-(2-hydroxypropan-2-yl)-3a-methyl-10-methylidene-1h,2h,3h,4h,7h,8h,9h,11h,12h,12ah-cyclopenta[11]annulen-6-yl]methoxy}-3-hydroxy-3-methyl-5-oxopentanoic acid (NP0246380)

MOL for NP0246380 ((3s)-5-{[(1r,3as,4s,9r,12as)-4,9-dihydroxy-1-(2-hydroxypropan-2-yl)-3a-methyl-10-methylidene-1h,2h,3h,4h,7h,8h,9h,11h,12h,12ah-cyclopenta[11]annulen-6-yl]methoxy}-3-hydroxy-3-methyl-5-oxopentanoic acid)

3D MOL for NP0246380 ((3s)-5-{[(1r,3as,4s,9r,12as)-4,9-dihydroxy-1-(2-hydroxypropan-2-yl)-3a-methyl-10-methylidene-1h,2h,3h,4h,7h,8h,9h,11h,12h,12ah-cyclopenta[11]annulen-6-yl]methoxy}-3-hydroxy-3-methyl-5-oxopentanoic acid)

3D SDF for NP0246380 ((3s)-5-{[(1r,3as,4s,9r,12as)-4,9-dihydroxy-1-(2-hydroxypropan-2-yl)-3a-methyl-10-methylidene-1h,2h,3h,4h,7h,8h,9h,11h,12h,12ah-cyclopenta[11]annulen-6-yl]methoxy}-3-hydroxy-3-methyl-5-oxopentanoic acid)

3D-SDF for NP0246380 ((3s)-5-{[(1r,3as,4s,9r,12as)-4,9-dihydroxy-1-(2-hydroxypropan-2-yl)-3a-methyl-10-methylidene-1h,2h,3h,4h,7h,8h,9h,11h,12h,12ah-cyclopenta[11]annulen-6-yl]methoxy}-3-hydroxy-3-methyl-5-oxopentanoic acid)

PDB for NP0246380 ((3s)-5-{[(1r,3as,4s,9r,12as)-4,9-dihydroxy-1-(2-hydroxypropan-2-yl)-3a-methyl-10-methylidene-1h,2h,3h,4h,7h,8h,9h,11h,12h,12ah-cyclopenta[11]annulen-6-yl]methoxy}-3-hydroxy-3-methyl-5-oxopentanoic acid)

3D PDB for NP0246380 ((3s)-5-{[(1r,3as,4s,9r,12as)-4,9-dihydroxy-1-(2-hydroxypropan-2-yl)-3a-methyl-10-methylidene-1h,2h,3h,4h,7h,8h,9h,11h,12h,12ah-cyclopenta[11]annulen-6-yl]methoxy}-3-hydroxy-3-methyl-5-oxopentanoic acid)

SMILES for NP0246380 ((3s)-5-{[(1r,3as,4s,9r,12as)-4,9-dihydroxy-1-(2-hydroxypropan-2-yl)-3a-methyl-10-methylidene-1h,2h,3h,4h,7h,8h,9h,11h,12h,12ah-cyclopenta[11]annulen-6-yl]methoxy}-3-hydroxy-3-methyl-5-oxopentanoic acid)

INCHI for NP0246380 ((3s)-5-{[(1r,3as,4s,9r,12as)-4,9-dihydroxy-1-(2-hydroxypropan-2-yl)-3a-methyl-10-methylidene-1h,2h,3h,4h,7h,8h,9h,11h,12h,12ah-cyclopenta[11]annulen-6-yl]methoxy}-3-hydroxy-3-methyl-5-oxopentanoic acid)

Structure for NP0246380 ((3s)-5-{[(1r,3as,4s,9r,12as)-4,9-dihydroxy-1-(2-hydroxypropan-2-yl)-3a-methyl-10-methylidene-1h,2h,3h,4h,7h,8h,9h,11h,12h,12ah-cyclopenta[11]annulen-6-yl]methoxy}-3-hydroxy-3-methyl-5-oxopentanoic acid)

3D Structure for NP0246380 ((3s)-5-{[(1r,3as,4s,9r,12as)-4,9-dihydroxy-1-(2-hydroxypropan-2-yl)-3a-methyl-10-methylidene-1h,2h,3h,4h,7h,8h,9h,11h,12h,12ah-cyclopenta[11]annulen-6-yl]methoxy}-3-hydroxy-3-methyl-5-oxopentanoic acid)