NP-MRD: Showing NP-Card for hopane-29-acetate (NP0164491)

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Record Information

Version

1.0

Created at

2022-09-02 23:22:43 UTC

Updated at

2022-09-02 23:22:43 UTC

NP-MRD ID

NP0164491

Secondary Accession Numbers

None

Natural Product Identification

Common Name

hopane-29-acetate

Description

Hopane-29-acetate, also known as dryocrassyl acetate, belongs to the class of organic compounds known as hopanoids. These are terpenoids containing hopane skeleton(A'-Neogammacerane), a pentacyclic structure with four cyclohexane rings and one cyclopentane ring (and often, a side chain emerging from C30). Based on a literature review very few articles have been published on hopane-29-acetate.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309032201222D          

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M  END

     RDKit          3D

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M  END


  Mrv1652309032201222D          

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    1.1378    1.1206    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.5611    1.8287    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3860    1.8162    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7876    1.0955    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.7139    1.9172    0.0000 C   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
  8  6  1  1  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  1  0  0  0
 11 13  1  0  0  0  0
  8 13  1  0  0  0  0
 13 14  1  1  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  1  0  0  0
 16 18  1  0  0  0  0
 11 18  1  0  0  0  0
 18 19  1  1  0  0  0
 19 20  1  0  0  0  0
 21 20  1  6  0  0  0
 21 22  1  0  0  0  0
 22 23  1  6  0  0  0
 22 24  1  0  0  0  0
 24 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
 27 29  1  0  0  0  0
 27 30  1  0  0  0  0
 22 30  1  0  0  0  0
 30 31  1  6  0  0  0
 31 32  1  0  0  0  0
 32 33  1  0  0  0  0
 21 33  1  0  0  0  0
 16 33  1  0  0  0  0
 33 34  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0164491

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(COC(C)=O)[C@H]1CC[C@@]2(C)[C@H]1CC[C@]1(C)[C@@H]2CC[C@@H]2[C@@]3(C)CCCC(C)(C)[C@@H]3CC[C@@]12C

> <INCHI_IDENTIFIER>
InChI=1S/C32H54O2/c1-21(20-34-22(2)33)23-12-17-29(5)24(23)13-18-31(7)26(29)10-11-27-30(6)16-9-15-28(3,4)25(30)14-19-32(27,31)8/h21,23-27H,9-20H2,1-8H3/t21?,23-,24+,25+,26-,27-,29+,30+,31-,32-/m1/s1

> <INCHI_KEY>
QSIMBUYUBYRBSU-ALPBESCQSA-N

> <FORMULA>
C32H54O2

> <MOLECULAR_WEIGHT>
470.782

> <EXACT_MASS>
470.412380979

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_ATOM_COUNT>
88

> <JCHEM_AVERAGE_POLARIZABILITY>
59.114402796364836

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-[(1R,2R,5S,6S,9S,10R,13R,14S,19S)-1,2,9,14,18,18-hexamethylpentacyclo[11.8.0.0^{2,10}.0^{5,9}.0^{14,19}]henicosan-6-yl]propyl acetate

> <ALOGPS_LOGP>
6.75

> <JCHEM_LOGP>
8.108903882666668

> <ALOGPS_LOGS>
-7.55

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-6.994419576680518

> <JCHEM_POLAR_SURFACE_AREA>
26.3

> <JCHEM_REFRACTIVITY>
140.61849999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.31e-05 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-[(1R,2R,5S,6S,9S,10R,13R,14S,19S)-1,2,9,14,18,18-hexamethylpentacyclo[11.8.0.0^{2,10}.0^{5,9}.0^{14,19}]henicosan-6-yl]propyl acetate

> <JCHEM_VEBER_RULE>
1

$$$$

HEADER    PROTEIN                                 03-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   03-SEP-22         0                                  
HETATM    1  C   UNK     0      17.719   3.674   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      16.559   2.661   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0      16.856   1.150   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0      15.101   3.159   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0      13.941   2.146   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      12.484   2.645   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      12.187   4.156   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      11.324   1.632   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      11.462   0.098   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      10.046  -0.507   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       9.033   0.653   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       8.385  -0.744   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       9.823   1.975   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       9.073   3.320   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       7.534   3.343   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       6.743   2.022   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       5.994   3.367   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       7.493   0.676   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       6.703  -0.645   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       5.163  -0.622   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       4.413   0.723   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       2.874   0.747   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       3.623  -0.599   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       2.083  -0.575   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       0.543  -0.552   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      -0.206   0.793   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       0.584   2.115   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      -0.855   2.664   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       0.875   3.628   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       2.124   2.092   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       2.914   3.414   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       4.454   3.390   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       5.204   2.045   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       5.066   3.579   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9   13                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12   13   18                                             
CONECT   12   11                                                            
CONECT   13   11    8   14                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17   18   33                                             
CONECT   17   16                                                            
CONECT   18   16   11   19                                                  
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22   33                                                  
CONECT   22   21   23   24   30                                             
CONECT   23   22                                                            
CONECT   24   22   25                                                       
CONECT   25   24   26                                                       
CONECT   26   25   27                                                       
CONECT   27   26   28   29   30                                             
CONECT   28   27                                                            
CONECT   29   27                                                            
CONECT   30   27   22   31                                                  
CONECT   31   30   32                                                       
CONECT   32   31   33                                                       
CONECT   33   32   21   16   34                                             
CONECT   34   33                                                            
MASTER        0    0    0    0    0    0    0    0   34    0   76    0
END

View in JSmol

Synonyms

Value	Source
Dryocrassyl acetate	ChEBI
Hopane-30-yl acetate	ChEBI
Dryocrassyl acetic acid	Generator
Hopane-30-yl acetic acid	Generator
Hopane-29-acetic acid	Generator

Chemical Formula

C₃₂H₅₄O₂

Average Mass

470.7820 Da

Monoisotopic Mass

470.41238 Da

IUPAC Name

2-[(1R,2R,5S,6S,9S,10R,13R,14S,19S)-1,2,9,14,18,18-hexamethylpentacyclo[11.8.0.0^{2,10}.0^{5,9}.0^{14,19}]henicosan-6-yl]propyl acetate

Traditional Name

2-[(1R,2R,5S,6S,9S,10R,13R,14S,19S)-1,2,9,14,18,18-hexamethylpentacyclo[11.8.0.0^{2,10}.0^{5,9}.0^{14,19}]henicosan-6-yl]propyl acetate

CAS Registry Number

Not Available

SMILES

CC(COC(C)=O)[C@H]1CC[C@@]2(C)[C@H]1CC[C@]1(C)[C@@H]2CC[C@@H]2[C@@]3(C)CCCC(C)(C)[C@@H]3CC[C@@]12C

InChI Identifier

InChI=1S/C32H54O2/c1-21(20-34-22(2)33)23-12-17-29(5)24(23)13-18-31(7)26(29)10-11-27-30(6)16-9-15-28(3,4)25(30)14-19-32(27,31)8/h21,23-27H,9-20H2,1-8H3/t21?,23-,24+,25+,26-,27-,29+,30+,31-,32-/m1/s1

InChI Key

QSIMBUYUBYRBSU-ALPBESCQSA-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 hopanoids. These are terpenoids containing hopane skeleton(A'-Neogammacerane), a pentacyclic structure with four cyclohexane rings and one cyclopentane ring (and often, a side chain emerging from C30).

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Hopanoids

Direct Parent

Hopanoids

Alternative Parents

Substituents

Triterpenoid
Hopane-skeleton
Steroid ester
Steroid
Carboxylic acid ester
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

acetate ester (CHEBI:5760 )
hopanoid (CHEBI:5760 )
pentacyclic triterpenoid (CHEBI:5760 )
Hopanoids (C08627 )
Hopanes (C08627 )
Hopanoids (LMPR04000003 )

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	6.75	ALOGPS
logP	8.11	ChemAxon
logS	-7.6	ALOGPS
pKa (Strongest Basic)	-7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	26.3 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	140.62 m³·mol⁻¹	ChemAxon
Polarizability	59.11 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	Yes	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

C00003748

Chemspider ID

390294

KEGG Compound ID

C08627

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

441680

PDB ID

Not Available

ChEBI ID

5760

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for hopane-29-acetate (NP0164491)

MOL for NP0164491 (hopane-29-acetate)

3D MOL for NP0164491 (hopane-29-acetate)

3D SDF for NP0164491 (hopane-29-acetate)

3D-SDF for NP0164491 (hopane-29-acetate)

PDB for NP0164491 (hopane-29-acetate)

3D PDB for NP0164491 (hopane-29-acetate)

SMILES for NP0164491 (hopane-29-acetate)

INCHI for NP0164491 (hopane-29-acetate)

Structure for NP0164491 (hopane-29-acetate)

3D Structure for NP0164491 (hopane-29-acetate)