NP-MRD: Showing NP-Card for 5-{[4-(acetyloxy)-1-(2-hydroxypropan-2-yl)-3a,10-dimethyl-1h,2h,3h,4h,7h,8h,11h,12h,12ah-cyclopenta[11]annulen-6-yl]methoxy}-3-hydroxy-3-methyl-5-oxopentanoic acid (NP0304579)

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Record Information

Version

2.0

Created at

2022-09-10 19:46:30 UTC

Updated at

2022-09-10 19:46:30 UTC

NP-MRD ID

NP0304579

Secondary Accession Numbers

None

Natural Product Identification

Common Name

5-{[4-(acetyloxy)-1-(2-hydroxypropan-2-yl)-3a,10-dimethyl-1h,2h,3h,4h,7h,8h,11h,12h,12ah-cyclopenta[11]annulen-6-yl]methoxy}-3-hydroxy-3-methyl-5-oxopentanoic acid

Description

5-{[4-(Acetyloxy)-1-(2-hydroxypropan-2-yl)-3a,10-dimethyl-1H,2H,3H,3aH,4H,7H,8H,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 dolabellane and neodolabellane diterpenoids. These are diterpenoids with a structure based on the dolabellane skeleton (3a,6,10-trimethyl-1-(propan-2-yl)-cyclopenta[11]annulene) or the neodolabellane skeleton. 5-{[4-(Acetyloxy)-1-(2-hydroxypropan-2-yl)-3a,10-dimethyl-1H,2H,3H,3aH,4H,7H,8H,11H,12H,12aH-cyclopenta[11]annulen-6-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


  Mrv1533004201500382D          

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M  END

     RDKit          3D

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M  END


  Mrv1533004201500382D          

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    0.0929   -1.8375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6663   -1.2443    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4076   -1.6062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1634   -0.8182    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1179   -3.3074    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2440   -4.0488    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6234   -2.9454    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8593   -3.6694    0.0000 O   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
  6  5  1  4  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 10 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 13 15  1  0  0  0  0
 13 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 17 19  1  0  0  0  0
  7 20  1  0  0  0  0
 20 21  1  0  0  0  0
 22 21  1  4  0  0  0
 22 23  2  0  0  0  0
 23 24  1  0  0  0  0
 23 25  1  0  0  0  0
 25 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
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
  5 31  1  0  0  0  0
 27 31  1  0  0  0  0
 31 32  1  0  0  0  0
 28 33  1  0  0  0  0
 33 34  1  0  0  0  0
 33 35  1  0  0  0  0
 33 36  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0304579

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(=O)OC1C=C(COC(=O)CC(C)(O)CC(O)=O)CCC=C(C)CCC2C(CCC12C)C(C)(C)O

> <INCHI_IDENTIFIER>
InChI=1S/C28H44O8/c1-18-8-7-9-20(17-35-25(32)16-27(5,34)15-24(30)31)14-23(36-19(2)29)28(6)13-12-21(26(3,4)33)22(28)11-10-18/h8,14,21-23,33-34H,7,9-13,15-17H2,1-6H3,(H,30,31)

> <INCHI_KEY>
XCJIFDKCCHFANV-UHFFFAOYSA-N

> <FORMULA>
C28H44O8

> <MOLECULAR_WEIGHT>
508.652

> <EXACT_MASS>
508.303618377

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
80

> <JCHEM_AVERAGE_POLARIZABILITY>
55.40587611873811

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

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

> <ALOGPS_LOGP>
4.13

> <JCHEM_LOGP>
3.1351890529999986

> <ALOGPS_LOGS>
-5.25

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
14.808041378587752

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.07501761470924

> <JCHEM_PKA_STRONGEST_BASIC>
-0.8403785686240172

> <JCHEM_POLAR_SURFACE_AREA>
130.36

> <JCHEM_REFRACTIVITY>
136.1698

> <JCHEM_ROTATABLE_BOND_COUNT>
10

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.89e-03 g/l

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

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 20-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   20-APR-15         0                                  
HETATM    1  C   UNK     0       4.999   0.663   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       3.506   0.285   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       2.432   1.389   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0       3.087  -1.197   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       4.161  -2.300   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.837  -0.917   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.362  -1.132   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       7.432  -0.024   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       8.926  -0.397   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       9.997   0.710   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       9.573   2.190   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0      11.491   0.337   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      12.561   1.444   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      11.454   2.514   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      13.668   0.374   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0      13.631   2.551   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      15.125   2.178   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      16.196   3.285   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0      15.549   0.698   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       6.629  -2.648   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       7.910  -3.743   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       7.695  -5.268   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       6.267  -5.844   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       6.052  -7.369   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       5.054  -4.896   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       3.626  -5.472   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       2.413  -4.523   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       0.896  -4.790   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       0.173  -3.430   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       1.244  -2.323   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       2.628  -2.998   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       2.172  -1.527   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       0.220  -6.174   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      -0.456  -7.558   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      -1.164  -5.498   0.000  0.00  0.00           C+0
HETATM   36  O   UNK     0       1.604  -6.850   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6   31                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8   20                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10   13                                                       
CONECT   13   12   14   15   16                                             
CONECT   14   13                                                            
CONECT   15   13                                                            
CONECT   16   13   17                                                       
CONECT   17   16   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17                                                            
CONECT   20    7   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23   26                                                       
CONECT   26   25   27                                                       
CONECT   27   26   28   31                                                  
CONECT   28   27   29   33                                                  
CONECT   29   28   30                                                       
CONECT   30   29   31                                                       
CONECT   31   30    5   27   32                                             
CONECT   32   31                                                            
CONECT   33   28   34   35   36                                             
CONECT   34   33                                                            
CONECT   35   33                                                            
CONECT   36   33                                                            
MASTER        0    0    0    0    0    0    0    0   36    0   74    0
END

View in JSmol

Synonyms

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

Chemical Formula

C₂₈H₄₄O₈

Average Mass

508.6520 Da

Monoisotopic Mass

508.30362 Da

IUPAC Name

5-{[4-(acetyloxy)-1-(2-hydroxypropan-2-yl)-3a,10-dimethyl-1H,2H,3H,3aH,4H,7H,8H,11H,12H,12aH-cyclopenta[11]annulen-6-yl]methoxy}-3-hydroxy-3-methyl-5-oxopentanoic acid

Traditional Name

5-{[4-(acetyloxy)-1-(2-hydroxypropan-2-yl)-3a,10-dimethyl-1H,2H,3H,4H,7H,8H,11H,12H,12aH-cyclopenta[11]annulen-6-yl]methoxy}-3-hydroxy-3-methyl-5-oxopentanoic acid

CAS Registry Number

Not Available

SMILES

CC(=O)OC1C=C(COC(=O)CC(C)(O)CC(O)=O)CCC=C(C)CCC2C(CCC12C)C(C)(C)O

InChI Identifier

InChI=1S/C28H44O8/c1-18-8-7-9-20(17-35-25(32)16-27(5,34)15-24(30)31)14-23(36-19(2)29)28(6)13-12-21(26(3,4)33)22(28)11-10-18/h8,14,21-23,33-34H,7,9-13,15-17H2,1-6H3,(H,30,31)

InChI Key

XCJIFDKCCHFANV-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 dolabellane and neodolabellane diterpenoids. These are diterpenoids with a structure based on the dolabellane skeleton (3a,6,10-trimethyl-1-(propan-2-yl)-cyclopenta[11]annulene) or the neodolabellane skeleton.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Diterpenoids

Direct Parent

Dolabellane and neodolabellane diterpenoids

Alternative Parents

Substituents

Dolabellane diterpenoid
Tricarboxylic acid or derivatives
Fatty acid ester
Fatty acyl
Tertiary alcohol
Carboxylic acid ester
Carboxylic acid
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Alcohol
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	4.13	ALOGPS
logP	3.14	ChemAxon
logS	-5.2	ALOGPS
pKa (Strongest Acidic)	4.08	ChemAxon
pKa (Strongest Basic)	-0.84	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	130.36 Å²	ChemAxon
Rotatable Bond Count	10	ChemAxon
Refractivity	136.17 m³·mol⁻¹	ChemAxon
Polarizability	55.41 Å³	ChemAxon
Number of Rings	2	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

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-{[4-(acetyloxy)-1-(2-hydroxypropan-2-yl)-3a,10-dimethyl-1h,2h,3h,4h,7h,8h,11h,12h,12ah-cyclopenta[11]annulen-6-yl]methoxy}-3-hydroxy-3-methyl-5-oxopentanoic acid (NP0304579)

MOL for NP0304579 (5-{[4-(acetyloxy)-1-(2-hydroxypropan-2-yl)-3a,10-dimethyl-1h,2h,3h,4h,7h,8h,11h,12h,12ah-cyclopenta[11]annulen-6-yl]methoxy}-3-hydroxy-3-methyl-5-oxopentanoic acid)

3D MOL for NP0304579 (5-{[4-(acetyloxy)-1-(2-hydroxypropan-2-yl)-3a,10-dimethyl-1h,2h,3h,4h,7h,8h,11h,12h,12ah-cyclopenta[11]annulen-6-yl]methoxy}-3-hydroxy-3-methyl-5-oxopentanoic acid)

3D SDF for NP0304579 (5-{[4-(acetyloxy)-1-(2-hydroxypropan-2-yl)-3a,10-dimethyl-1h,2h,3h,4h,7h,8h,11h,12h,12ah-cyclopenta[11]annulen-6-yl]methoxy}-3-hydroxy-3-methyl-5-oxopentanoic acid)

3D-SDF for NP0304579 (5-{[4-(acetyloxy)-1-(2-hydroxypropan-2-yl)-3a,10-dimethyl-1h,2h,3h,4h,7h,8h,11h,12h,12ah-cyclopenta[11]annulen-6-yl]methoxy}-3-hydroxy-3-methyl-5-oxopentanoic acid)

PDB for NP0304579 (5-{[4-(acetyloxy)-1-(2-hydroxypropan-2-yl)-3a,10-dimethyl-1h,2h,3h,4h,7h,8h,11h,12h,12ah-cyclopenta[11]annulen-6-yl]methoxy}-3-hydroxy-3-methyl-5-oxopentanoic acid)

3D PDB for NP0304579 (5-{[4-(acetyloxy)-1-(2-hydroxypropan-2-yl)-3a,10-dimethyl-1h,2h,3h,4h,7h,8h,11h,12h,12ah-cyclopenta[11]annulen-6-yl]methoxy}-3-hydroxy-3-methyl-5-oxopentanoic acid)

SMILES for NP0304579 (5-{[4-(acetyloxy)-1-(2-hydroxypropan-2-yl)-3a,10-dimethyl-1h,2h,3h,4h,7h,8h,11h,12h,12ah-cyclopenta[11]annulen-6-yl]methoxy}-3-hydroxy-3-methyl-5-oxopentanoic acid)

INCHI for NP0304579 (5-{[4-(acetyloxy)-1-(2-hydroxypropan-2-yl)-3a,10-dimethyl-1h,2h,3h,4h,7h,8h,11h,12h,12ah-cyclopenta[11]annulen-6-yl]methoxy}-3-hydroxy-3-methyl-5-oxopentanoic acid)

Structure for NP0304579 (5-{[4-(acetyloxy)-1-(2-hydroxypropan-2-yl)-3a,10-dimethyl-1h,2h,3h,4h,7h,8h,11h,12h,12ah-cyclopenta[11]annulen-6-yl]methoxy}-3-hydroxy-3-methyl-5-oxopentanoic acid)

3D Structure for NP0304579 (5-{[4-(acetyloxy)-1-(2-hydroxypropan-2-yl)-3a,10-dimethyl-1h,2h,3h,4h,7h,8h,11h,12h,12ah-cyclopenta[11]annulen-6-yl]methoxy}-3-hydroxy-3-methyl-5-oxopentanoic acid)