NP-MRD: Showing NP-Card for 10-(acetyloxy)-2,2,9,9,12a,14a-hexamethyl-3,4,5,6b,7,8,8a,10,11,12,12b,13,14,14b-tetradecahydro-1h-picene-4a-carboxylic acid (NP0179687)

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Record Information

Version

2.0

Created at

2022-09-03 17:54:48 UTC

Updated at

2022-09-03 17:54:48 UTC

NP-MRD ID

NP0179687

Secondary Accession Numbers

None

Natural Product Identification

Common Name

10-(acetyloxy)-2,2,9,9,12a,14a-hexamethyl-3,4,5,6b,7,8,8a,10,11,12,12b,13,14,14b-tetradecahydro-1h-picene-4a-carboxylic acid

Description

10-(Acetyloxy)-2,2,9,9,12a,14a-hexamethyl-1,2,3,4,4a,5,6b,7,8,8a,9,10,11,12,12a,12b,13,14,14a,14b-icosahydropicene-4a-carboxylic acid belongs to the class of organic compounds known as dicarboxylic acids and derivatives. These are organic compounds containing exactly two carboxylic acid groups. 10-(acetyloxy)-2,2,9,9,12a,14a-hexamethyl-3,4,5,6b,7,8,8a,10,11,12,12b,13,14,14b-tetradecahydro-1h-picene-4a-carboxylic acid is found in Croton cajucara. 10-(Acetyloxy)-2,2,9,9,12a,14a-hexamethyl-1,2,3,4,4a,5,6b,7,8,8a,9,10,11,12,12a,12b,13,14,14a,14b-icosahydropicene-4a-carboxylic acid is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004261513442D          

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M  END

     RDKit          3D

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M  END


  Mrv1533004261513442D          

 35 39  0  0  0  0            999 V2000
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    3.6020   -5.2520    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7770   -5.2520    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645   -5.9664    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5395   -5.9664    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1270   -5.2520    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3020   -5.2520    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2732   -6.0765    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3977   -5.6892    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6645   -5.9664    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2520   -6.6809    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4895   -5.9664    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
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  8 10  1  0  0  0  0
 10 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
 13 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 17 19  1  0  0  0  0
 17 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 15 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  2  0  0  0  0
 13 25  1  0  0  0  0
 25 26  1  0  0  0  0
 10 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
  8 29  1  0  0  0  0
 29 30  1  0  0  0  0
  5 30  1  0  0  0  0
 30 31  1  0  0  0  0
 30 32  1  0  0  0  0
 22 33  1  0  0  0  0
 33 34  2  0  0  0  0
 33 35  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0179687

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(=O)OC1CCC2(C)C3CCC4(C)C5CC(C)(C)CCC5(CC=C4C3CCC2C1(C)C)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C31H48O4/c1-19(32)35-25-12-14-29(6)21-10-13-30(7)22(20(21)8-9-23(29)28(25,4)5)11-15-31(26(33)34)17-16-27(2,3)18-24(30)31/h11,20-21,23-25H,8-10,12-18H2,1-7H3,(H,33,34)

> <INCHI_KEY>
OEHQMDICZNEUSV-UHFFFAOYSA-N

> <FORMULA>
C31H48O4

> <MOLECULAR_WEIGHT>
484.721

> <EXACT_MASS>
484.355260026

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
83

> <JCHEM_AVERAGE_POLARIZABILITY>
57.88937079197283

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
10-(acetyloxy)-2,2,9,9,12a,14a-hexamethyl-1,2,3,4,4a,5,6b,7,8,8a,9,10,11,12,12a,12b,13,14,14a,14b-icosahydropicene-4a-carboxylic acid

> <ALOGPS_LOGP>
6.60

> <JCHEM_LOGP>
6.735911723666666

> <ALOGPS_LOGS>
-6.27

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.71786222774145

> <JCHEM_PKA_STRONGEST_BASIC>
-7.003778164391425

> <JCHEM_POLAR_SURFACE_AREA>
63.60000000000001

> <JCHEM_REFRACTIVITY>
138.30089999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.58e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
10-(acetyloxy)-2,2,9,9,12a,14a-hexamethyl-3,4,5,6b,7,8,8a,10,11,12,12b,13,14,14b-tetradecahydro-1H-picene-4a-carboxylic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 26-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   26-APR-15         0                                  
HETATM    1  C   UNK     0      -4.056  -9.804   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -2.516  -9.804   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0      -1.746 -11.137   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0      -1.746  -8.470   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0      -0.206  -8.470   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.564  -7.136   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.104  -7.136   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.874  -8.470   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       3.644  -7.136   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.414  -8.470   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.184  -7.136   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       6.724  -7.136   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       7.494  -8.470   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       8.264  -7.136   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       9.034  -8.470   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       9.804  -7.136   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      11.344  -7.136   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      11.076  -5.620   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      12.791  -6.610   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      12.114  -8.470   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      11.344  -9.804   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       9.804  -9.804   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       9.034 -11.137   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       7.494 -11.137   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       6.724  -9.804   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       5.184  -9.804   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       4.414 -11.137   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       2.874 -11.137   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       2.104  -9.804   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       0.564  -9.804   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       0.510 -11.343   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      -0.742 -10.620   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      10.574 -11.137   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0       9.804 -12.471   0.000  0.00  0.00           O+0
HETATM   35  O   UNK     0      12.114 -11.137   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   30                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9   10   29                                             
CONECT    9    8                                                            
CONECT   10    8   11   26                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14   15   25                                             
CONECT   14   13                                                            
CONECT   15   13   16   22                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18   19   20                                             
CONECT   18   17                                                            
CONECT   19   17                                                            
CONECT   20   17   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   15   23   33                                             
CONECT   23   22   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24   13   26                                                  
CONECT   26   25   10   27                                                  
CONECT   27   26   28                                                       
CONECT   28   27   29                                                       
CONECT   29   28    8   30                                                  
CONECT   30   29    5   31   32                                             
CONECT   31   30                                                            
CONECT   32   30                                                            
CONECT   33   22   34   35                                                  
CONECT   34   33                                                            
CONECT   35   33                                                            
MASTER        0    0    0    0    0    0    0    0   35    0   78    0
END

View in JSmol

Synonyms

Value	Source
10-(Acetyloxy)-2,2,9,9,12a,14a-hexamethyl-1,2,3,4,4a,5,6b,7,8,8a,9,10,11,12,12a,12b,13,14,14a,14b-icosahydropicene-4a-carboxylate	Generator

Chemical Formula

C₃₁H₄₈O₄

Average Mass

484.7210 Da

Monoisotopic Mass

484.35526 Da

IUPAC Name

10-(acetyloxy)-2,2,9,9,12a,14a-hexamethyl-1,2,3,4,4a,5,6b,7,8,8a,9,10,11,12,12a,12b,13,14,14a,14b-icosahydropicene-4a-carboxylic acid

Traditional Name

10-(acetyloxy)-2,2,9,9,12a,14a-hexamethyl-3,4,5,6b,7,8,8a,10,11,12,12b,13,14,14b-tetradecahydro-1H-picene-4a-carboxylic acid

CAS Registry Number

Not Available

SMILES

CC(=O)OC1CCC2(C)C3CCC4(C)C5CC(C)(C)CCC5(CC=C4C3CCC2C1(C)C)C(O)=O

InChI Identifier

InChI=1S/C31H48O4/c1-19(32)35-25-12-14-29(6)21-10-13-30(7)22(20(21)8-9-23(29)28(25,4)5)11-15-31(26(33)34)17-16-27(2,3)18-24(30)31/h11,20-21,23-25H,8-10,12-18H2,1-7H3,(H,33,34)

InChI Key

OEHQMDICZNEUSV-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

Species Name	Source	Reference
Croton cajucara	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as dicarboxylic acids and derivatives. These are organic compounds containing exactly two carboxylic acid groups.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Dicarboxylic acids and derivatives

Direct Parent

Dicarboxylic acids and derivatives

Alternative Parents

Substituents

Dicarboxylic acid or derivatives
Carboxylic acid ester
Carboxylic acid
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
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	6.6	ALOGPS
logP	6.74	ChemAxon
logS	-6.3	ALOGPS
pKa (Strongest Acidic)	4.72	ChemAxon
pKa (Strongest Basic)	-7	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	63.6 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	138.3 m³·mol⁻¹	ChemAxon
Polarizability	57.89 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	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 10-(acetyloxy)-2,2,9,9,12a,14a-hexamethyl-3,4,5,6b,7,8,8a,10,11,12,12b,13,14,14b-tetradecahydro-1h-picene-4a-carboxylic acid (NP0179687)

MOL for NP0179687 (10-(acetyloxy)-2,2,9,9,12a,14a-hexamethyl-3,4,5,6b,7,8,8a,10,11,12,12b,13,14,14b-tetradecahydro-1h-picene-4a-carboxylic acid)

3D MOL for NP0179687 (10-(acetyloxy)-2,2,9,9,12a,14a-hexamethyl-3,4,5,6b,7,8,8a,10,11,12,12b,13,14,14b-tetradecahydro-1h-picene-4a-carboxylic acid)

3D SDF for NP0179687 (10-(acetyloxy)-2,2,9,9,12a,14a-hexamethyl-3,4,5,6b,7,8,8a,10,11,12,12b,13,14,14b-tetradecahydro-1h-picene-4a-carboxylic acid)

3D-SDF for NP0179687 (10-(acetyloxy)-2,2,9,9,12a,14a-hexamethyl-3,4,5,6b,7,8,8a,10,11,12,12b,13,14,14b-tetradecahydro-1h-picene-4a-carboxylic acid)

PDB for NP0179687 (10-(acetyloxy)-2,2,9,9,12a,14a-hexamethyl-3,4,5,6b,7,8,8a,10,11,12,12b,13,14,14b-tetradecahydro-1h-picene-4a-carboxylic acid)

3D PDB for NP0179687 (10-(acetyloxy)-2,2,9,9,12a,14a-hexamethyl-3,4,5,6b,7,8,8a,10,11,12,12b,13,14,14b-tetradecahydro-1h-picene-4a-carboxylic acid)

SMILES for NP0179687 (10-(acetyloxy)-2,2,9,9,12a,14a-hexamethyl-3,4,5,6b,7,8,8a,10,11,12,12b,13,14,14b-tetradecahydro-1h-picene-4a-carboxylic acid)

INCHI for NP0179687 (10-(acetyloxy)-2,2,9,9,12a,14a-hexamethyl-3,4,5,6b,7,8,8a,10,11,12,12b,13,14,14b-tetradecahydro-1h-picene-4a-carboxylic acid)

Structure for NP0179687 (10-(acetyloxy)-2,2,9,9,12a,14a-hexamethyl-3,4,5,6b,7,8,8a,10,11,12,12b,13,14,14b-tetradecahydro-1h-picene-4a-carboxylic acid)

3D Structure for NP0179687 (10-(acetyloxy)-2,2,9,9,12a,14a-hexamethyl-3,4,5,6b,7,8,8a,10,11,12,12b,13,14,14b-tetradecahydro-1h-picene-4a-carboxylic acid)