NP-MRD: Showing NP-Card for (3s,3as,4s,5ar,5br,7s,7as,11ar,11br,13ar,13br)-7-hydroxy-3-(2-hydroxypropan-2-yl)-5a,5b,8,8,11a,13b-hexamethyl-hexadecahydrocyclopenta[a]chrysen-4-yl acetate (NP0157629)

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Record Information

Version

2.0

Created at

2022-09-02 15:03:12 UTC

Updated at

2022-09-02 15:03:12 UTC

NP-MRD ID

NP0157629

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(3s,3as,4s,5ar,5br,7s,7as,11ar,11br,13ar,13br)-7-hydroxy-3-(2-hydroxypropan-2-yl)-5a,5b,8,8,11a,13b-hexamethyl-hexadecahydrocyclopenta[a]chrysen-4-yl acetate

Description

16Beta-acetoxy-hopane-6alpha,22-diol 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). Thus, 16beta-acetoxy-hopane-6alpha,22-diol is considered to be a hopanoid. (3s,3as,4s,5ar,5br,7s,7as,11ar,11br,13ar,13br)-7-hydroxy-3-(2-hydroxypropan-2-yl)-5a,5b,8,8,11a,13b-hexamethyl-hexadecahydrocyclopenta[a]chrysen-4-yl acetate is found in Physcia aipolia. Based on a literature review very few articles have been published on 16beta-acetoxy-hopane-6alpha,22-diol.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309022217032D          

 36 40  0  0  1  0            999 V2000
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M  END

     RDKit          3D

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M  END


  Mrv1652309022217032D          

 36 40  0  0  1  0            999 V2000
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    6.0346   -3.7023    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4362   -4.4230    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0129   -5.1311    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7838   -5.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8573   -5.9413    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1880   -5.1186    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.7647   -5.8267    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.1663   -6.5473    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9398   -5.8141    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5382   -5.0935    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.6119   -5.9152    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4868   -4.3477    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.8338   -3.5992    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9442   -3.7263    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1855   -4.0503    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2592   -4.8720    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.3622   -5.4147    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9836   -5.9573    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9048   -4.7933    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1804   -6.0361    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0635   -5.0558    0.0000 C   0  0  2  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
  5  4  1  6  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  1  0  0  0
  7  9  1  0  0  0  0
  9 10  1  1  0  0  0
 10 11  1  0  0  0  0
 12 11  1  6  0  0  0
 12 13  1  0  0  0  0
 13 14  1  6  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
 18 19  1  0  0  0  0
 18 20  1  0  0  0  0
 21 18  1  6  0  0  0
 13 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  1  0  0  0
 22 24  1  0  0  0  0
 24 25  1  0  0  0  0
 12 25  1  0  0  0  0
  7 25  1  0  0  0  0
 25 26  1  6  0  0  0
  9 27  1  0  0  0  0
 27 28  1  1  0  0  0
 27 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
 31 32  1  1  0  0  0
 32 33  1  0  0  0  0
 32 34  1  0  0  0  0
 32 35  1  0  0  0  0
 36 31  1  1  0  0  0
  5 36  1  0  0  0  0
 27 36  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0157629

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(=O)O[C@H]1C[C@]2(C)[C@H](CC[C@@H]3[C@@]4(C)CCCC(C)(C)[C@@H]4[C@@H](O)C[C@@]23C)[C@@]2(C)CC[C@@H]([C@H]12)C(C)(C)O

> <INCHI_IDENTIFIER>
InChI=1S/C32H54O4/c1-19(33)36-22-18-32(9)23(29(6)16-13-20(25(22)29)28(4,5)35)11-12-24-30(7)15-10-14-27(2,3)26(30)21(34)17-31(24,32)8/h20-26,34-35H,10-18H2,1-9H3/t20-,21-,22-,23+,24+,25+,26-,29+,30+,31+,32+/m0/s1

> <INCHI_KEY>
MZAOKSLVDCHHKU-WZNQLRTQSA-N

> <FORMULA>
C32H54O4

> <MOLECULAR_WEIGHT>
502.78

> <EXACT_MASS>
502.402210219

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
90

> <JCHEM_AVERAGE_POLARIZABILITY>
60.62928682783971

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1R,2R,4S,5S,6S,9R,10R,13R,14R,19S,20S)-20-hydroxy-6-(2-hydroxypropan-2-yl)-1,2,9,14,18,18-hexamethylpentacyclo[11.8.0.0^{2,10}.0^{5,9}.0^{14,19}]henicosan-4-yl acetate

> <ALOGPS_LOGP>
5.26

> <JCHEM_LOGP>
5.456938220333334

> <ALOGPS_LOGS>
-6.19

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
15.054622455864358

> <JCHEM_PKA_STRONGEST_BASIC>
-0.17427979947989536

> <JCHEM_POLAR_SURFACE_AREA>
66.76

> <JCHEM_REFRACTIVITY>
143.7109

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
3.24e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1R,2R,4S,5S,6S,9R,10R,13R,14R,19S,20S)-20-hydroxy-6-(2-hydroxypropan-2-yl)-1,2,9,14,18,18-hexamethylpentacyclo[11.8.0.0^{2,10}.0^{5,9}.0^{14,19}]henicosan-4-yl acetate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 02-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   02-SEP-22         0                                  
HETATM    1  C   UNK     0       1.904 -14.772   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.694 -13.450   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       4.234 -13.473   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0       1.945 -12.105   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       2.735 -10.783   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.275 -10.806   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       5.065  -9.484   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       5.814 -10.830   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.315  -8.139   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.105  -6.817   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       6.645  -6.841   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       7.395  -8.186   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       8.935  -8.209   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       8.185  -6.864   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       9.725  -6.888   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      11.265  -6.911   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      12.014  -8.256   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      11.224  -9.578   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      12.663 -10.127   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      10.934 -11.090   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       9.684  -9.555   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       8.894 -10.876   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       9.644 -12.222   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0       7.354 -10.853   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       6.605  -9.508   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       6.742 -11.042   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       2.775  -8.116   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       3.423  -6.719   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       1.762  -6.956   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       0.346  -7.561   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       0.484  -9.094   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      -0.676 -10.107   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      -1.836 -11.120   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      -1.689  -8.947   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0       0.337 -11.267   0.000  0.00  0.00           O+0
HETATM   36  C   UNK     0       1.985  -9.438   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   36                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8    9   25                                             
CONECT    8    7                                                            
CONECT    9    7   10   27                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13   25                                                  
CONECT   13   12   14   15   21                                             
CONECT   14   13                                                            
CONECT   15   13   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19   20   21                                             
CONECT   19   18                                                            
CONECT   20   18                                                            
CONECT   21   18   13   22                                                  
CONECT   22   21   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22   25                                                       
CONECT   25   24   12    7   26                                             
CONECT   26   25                                                            
CONECT   27    9   28   29   36                                             
CONECT   28   27                                                            
CONECT   29   27   30                                                       
CONECT   30   29   31                                                       
CONECT   31   30   32   36                                                  
CONECT   32   31   33   34   35                                             
CONECT   33   32                                                            
CONECT   34   32                                                            
CONECT   35   32                                                            
CONECT   36   31    5   27                                                  
MASTER        0    0    0    0    0    0    0    0   36    0   80    0
END

View in JSmol

Synonyms

Value	Source
16b-Acetoxy-hopane-6a,22-diol	Generator
16Β-acetoxy-hopane-6α,22-diol	Generator

Chemical Formula

C₃₂H₅₄O₄

Average Mass

502.7800 Da

Monoisotopic Mass

502.40221 Da

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

CC(=O)O[C@H]1C[C@]2(C)[C@H](CC[C@@H]3[C@@]4(C)CCCC(C)(C)[C@@H]4[C@@H](O)C[C@@]23C)[C@@]2(C)CC[C@@H]([C@H]12)C(C)(C)O

InChI Identifier

InChI=1S/C32H54O4/c1-19(33)36-22-18-32(9)23(29(6)16-13-20(25(22)29)28(4,5)35)11-12-24-30(7)15-10-14-27(2,3)26(30)21(34)17-31(24,32)8/h20-26,34-35H,10-18H2,1-9H3/t20-,21-,22-,23+,24+,25+,26-,29+,30+,31+,32+/m0/s1

InChI Key

MZAOKSLVDCHHKU-WZNQLRTQSA-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
Physcia aipolia	LOTUS Database	35616633

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

Hopane-skeleton
Triterpenoid
20-hydroxysteroid
Steroid ester
2-hydroxysteroid
Hydroxysteroid
Steroid
Cyclic alcohol
Tertiary alcohol
Carboxylic acid ester
Secondary alcohol
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Alcohol
Carbonyl group
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

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

10197949

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

21582905

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (3s,3as,4s,5ar,5br,7s,7as,11ar,11br,13ar,13br)-7-hydroxy-3-(2-hydroxypropan-2-yl)-5a,5b,8,8,11a,13b-hexamethyl-hexadecahydrocyclopenta[a]chrysen-4-yl acetate (NP0157629)

MOL for NP0157629 ((3s,3as,4s,5ar,5br,7s,7as,11ar,11br,13ar,13br)-7-hydroxy-3-(2-hydroxypropan-2-yl)-5a,5b,8,8,11a,13b-hexamethyl-hexadecahydrocyclopenta[a]chrysen-4-yl acetate)

3D MOL for NP0157629 ((3s,3as,4s,5ar,5br,7s,7as,11ar,11br,13ar,13br)-7-hydroxy-3-(2-hydroxypropan-2-yl)-5a,5b,8,8,11a,13b-hexamethyl-hexadecahydrocyclopenta[a]chrysen-4-yl acetate)

3D SDF for NP0157629 ((3s,3as,4s,5ar,5br,7s,7as,11ar,11br,13ar,13br)-7-hydroxy-3-(2-hydroxypropan-2-yl)-5a,5b,8,8,11a,13b-hexamethyl-hexadecahydrocyclopenta[a]chrysen-4-yl acetate)

3D-SDF for NP0157629 ((3s,3as,4s,5ar,5br,7s,7as,11ar,11br,13ar,13br)-7-hydroxy-3-(2-hydroxypropan-2-yl)-5a,5b,8,8,11a,13b-hexamethyl-hexadecahydrocyclopenta[a]chrysen-4-yl acetate)

PDB for NP0157629 ((3s,3as,4s,5ar,5br,7s,7as,11ar,11br,13ar,13br)-7-hydroxy-3-(2-hydroxypropan-2-yl)-5a,5b,8,8,11a,13b-hexamethyl-hexadecahydrocyclopenta[a]chrysen-4-yl acetate)

3D PDB for NP0157629 ((3s,3as,4s,5ar,5br,7s,7as,11ar,11br,13ar,13br)-7-hydroxy-3-(2-hydroxypropan-2-yl)-5a,5b,8,8,11a,13b-hexamethyl-hexadecahydrocyclopenta[a]chrysen-4-yl acetate)

SMILES for NP0157629 ((3s,3as,4s,5ar,5br,7s,7as,11ar,11br,13ar,13br)-7-hydroxy-3-(2-hydroxypropan-2-yl)-5a,5b,8,8,11a,13b-hexamethyl-hexadecahydrocyclopenta[a]chrysen-4-yl acetate)

INCHI for NP0157629 ((3s,3as,4s,5ar,5br,7s,7as,11ar,11br,13ar,13br)-7-hydroxy-3-(2-hydroxypropan-2-yl)-5a,5b,8,8,11a,13b-hexamethyl-hexadecahydrocyclopenta[a]chrysen-4-yl acetate)

Structure for NP0157629 ((3s,3as,4s,5ar,5br,7s,7as,11ar,11br,13ar,13br)-7-hydroxy-3-(2-hydroxypropan-2-yl)-5a,5b,8,8,11a,13b-hexamethyl-hexadecahydrocyclopenta[a]chrysen-4-yl acetate)

3D Structure for NP0157629 ((3s,3as,4s,5ar,5br,7s,7as,11ar,11br,13ar,13br)-7-hydroxy-3-(2-hydroxypropan-2-yl)-5a,5b,8,8,11a,13b-hexamethyl-hexadecahydrocyclopenta[a]chrysen-4-yl acetate)