NP-MRD: Showing NP-Card for (2s,3r,4r,7s)-7-[(3r,3as,5ar,5br,7as,11as,11br,13ar,13bs)-5a,5b,8,8,11a,13b-hexamethyl-hexadecahydrocyclopenta[a]chrysen-3-yl]-1-aminooctane-2,3,4-triol (NP0240069)

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Record Information

Version

2.0

Created at

2022-09-06 23:47:21 UTC

Updated at

2022-09-06 23:47:21 UTC

NP-MRD ID

NP0240069

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(2s,3r,4r,7s)-7-[(3r,3as,5ar,5br,7as,11as,11br,13ar,13bs)-5a,5b,8,8,11a,13b-hexamethyl-hexadecahydrocyclopenta[a]chrysen-3-yl]-1-aminooctane-2,3,4-triol

Description

Aminobacteriohopanetriol belongs to the class of organic compounds known as bacteriohopanoids. These are bacterial terpenoids structurally characterized by a C30 skeleton, which is usually conjugated to a C5 (usually hydroxylated) unit linked by a carbon-carbon bond. (2s,3r,4r,7s)-7-[(3r,3as,5ar,5br,7as,11as,11br,13ar,13bs)-5a,5b,8,8,11a,13b-hexamethyl-hexadecahydrocyclopenta[a]chrysen-3-yl]-1-aminooctane-2,3,4-triol is found in Rhodoblastus acidophilus. (2s,3r,4r,7s)-7-[(3r,3as,5ar,5br,7as,11as,11br,13ar,13bs)-5a,5b,8,8,11a,13b-hexamethyl-hexadecahydrocyclopenta[a]chrysen-3-yl]-1-aminooctane-2,3,4-triol was first documented in 2012 (PMID: 22221333). Based on a literature review a small amount of articles have been published on aminobacteriohopanetriol (PMID: 35736196) (PMID: 26032177) (PMID: 25155017) (PMID: 25117430).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309072201472D          

 39 43  0  0  1  0            999 V2000
    1.8094   -4.7201    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8094   -5.5451    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
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    3.9529   -6.7826    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    6.0963   -5.5451    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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  2  1  1  1  0  0  0
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  3  4  1  0  0  0  0
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  5  6  1  6  0  0  0
  5  7  1  0  0  0  0
  7  8  1  1  0  0  0
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  9 10  1  6  0  0  0
  9 11  1  0  0  0  0
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 13  2  1  1  0  0  0
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 38 39  1  6  0  0  0
M  END

     RDKit          3D

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 30 85  1  0
 30 86  1  0
 31 87  1  0
 31 88  1  0
 33 89  1  0
 33 90  1  0
 33 91  1  0
 34 92  1  0
 34 93  1  0
 34 94  1  0
 35 95  1  1
 36 96  1  0
 36 97  1  0
 37 98  1  0
 37 99  1  0
 39100  1  0
 39101  1  0
 39102  1  0
M  END


  Mrv1652309072201472D          

 39 43  0  0  1  0            999 V2000
    1.8094   -4.7201    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8094   -5.5451    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.5239   -5.9576    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2384   -5.5451    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9529   -5.9576    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.9529   -6.7826    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6673   -5.5451    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.6673   -4.7201    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3818   -5.9576    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.3818   -6.7826    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0963   -5.5451    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8107   -5.9576    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.0950   -5.9576    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.0087   -6.7780    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2018   -6.9496    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2107   -6.2351    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.6957   -6.9025    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3413   -5.6220    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0864   -4.8374    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7206   -4.6659    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2726   -5.2790    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.5276   -4.4943    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0177   -6.0636    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.5697   -6.6767    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3767   -6.5051    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6316   -5.7205    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.4386   -5.5490    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.1837   -6.3336    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9907   -6.1621    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7976   -5.9906    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0526   -5.2059    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5005   -4.5928    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2002   -4.1557    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1915   -3.8279    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6936   -4.7644    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.1415   -4.1513    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3346   -4.3228    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0796   -5.1074    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.9934   -4.2869    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  1  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  6  0  0  0
  5  7  1  0  0  0  0
  7  8  1  1  0  0  0
  7  9  1  0  0  0  0
  9 10  1  6  0  0  0
  9 11  1  0  0  0  0
 11 12  1  0  0  0  0
 13  2  1  1  0  0  0
 13 14  1  0  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
 13 18  1  0  0  0  0
 18 19  1  1  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  1  0  0  0
 21 23  1  0  0  0  0
 16 23  1  0  0  0  0
 23 24  1  1  0  0  0
 24 25  1  0  0  0  0
 26 25  1  6  0  0  0
 26 27  1  0  0  0  0
 27 28  1  6  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  0  0  0  0
 32 33  1  0  0  0  0
 32 34  1  0  0  0  0
 32 35  1  0  0  0  0
 27 35  1  0  0  0  0
 35 36  1  6  0  0  0
 36 37  1  0  0  0  0
 37 38  1  0  0  0  0
 26 38  1  0  0  0  0
 21 38  1  0  0  0  0
 38 39  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0240069

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@@H](CC[C@@H](O)[C@@H](O)[C@@H](O)CN)[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/C35H63NO3/c1-22(9-10-25(37)30(39)26(38)21-36)23-13-18-32(4)24(23)14-19-34(6)28(32)11-12-29-33(5)17-8-16-31(2,3)27(33)15-20-35(29,34)7/h22-30,37-39H,8-21,36H2,1-7H3/t22-,23+,24-,25+,26-,27-,28+,29+,30+,32-,33-,34+,35+/m0/s1

> <INCHI_KEY>
DYJIJIUSBPCLMI-NUJFMENSSA-N

> <FORMULA>
C35H63NO3

> <MOLECULAR_WEIGHT>
545.893

> <EXACT_MASS>
545.480794893

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
102

> <JCHEM_AVERAGE_POLARIZABILITY>
68.16899136823551

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S,3R,4R,7S)-1-amino-7-[(1R,2R,5S,6R,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]octane-2,3,4-triol

> <JCHEM_LOGP>
6.481075449666665

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
14.431355876888944

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.058525639259393

> <JCHEM_PKA_STRONGEST_BASIC>
8.90856174716888

> <JCHEM_POLAR_SURFACE_AREA>
86.71

> <JCHEM_REFRACTIVITY>
160.29100000000003

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(2S,3R,4R,7S)-1-amino-7-[(1R,2R,5S,6R,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]octane-2,3,4-triol

> <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       3.378  -8.811   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       3.378 -10.351   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       4.711 -11.121   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       6.045 -10.351   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       7.379 -11.121   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       7.379 -12.661   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       8.712 -10.351   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       8.712  -8.811   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0      10.046 -11.121   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0      10.046 -12.661   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0      11.380 -10.351   0.000  0.00  0.00           C+0
HETATM   12  N   UNK     0      12.713 -11.121   0.000  0.00  0.00           N+0
HETATM   13  C   UNK     0       2.044 -11.121   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       1.883 -12.652   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       0.377 -12.973   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -0.393 -11.639   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -1.299 -12.885   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       0.637 -10.494   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       0.161  -9.030   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -1.345  -8.710   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -2.376  -9.854   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -2.851  -8.389   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -1.900 -11.319   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      -2.930 -12.463   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      -4.437 -12.143   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      -4.912 -10.678   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      -6.419 -10.358   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      -5.943 -11.823   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      -7.449 -11.503   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      -8.956 -11.182   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      -9.431  -9.718   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      -8.401  -8.573   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      -9.707  -7.757   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      -7.824  -7.145   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      -6.895  -8.893   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      -5.864  -7.749   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0      -4.358  -8.069   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0      -3.882  -9.534   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0      -3.721  -8.002   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   13                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12                                                       
CONECT   12   11                                                            
CONECT   13    2   14   18                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17   18   23                                             
CONECT   17   16                                                            
CONECT   18   16   13   19                                                  
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22   23   38                                             
CONECT   22   21                                                            
CONECT   23   21   16   24                                                  
CONECT   24   23   25                                                       
CONECT   25   24   26                                                       
CONECT   26   25   27   38                                                  
CONECT   27   26   28   29   35                                             
CONECT   28   27                                                            
CONECT   29   27   30                                                       
CONECT   30   29   31                                                       
CONECT   31   30   32                                                       
CONECT   32   31   33   34   35                                             
CONECT   33   32                                                            
CONECT   34   32                                                            
CONECT   35   32   27   36                                                  
CONECT   36   35   37                                                       
CONECT   37   36   38                                                       
CONECT   38   37   26   21   39                                             
CONECT   39   38                                                            
MASTER        0    0    0    0    0    0    0    0   39    0   86    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₃₅H₆₃NO₃

Average Mass

545.8930 Da

Monoisotopic Mass

545.48079 Da

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

C[C@@H](CC[C@@H](O)[C@@H](O)[C@@H](O)CN)[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/C35H63NO3/c1-22(9-10-25(37)30(39)26(38)21-36)23-13-18-32(4)24(23)14-19-34(6)28(32)11-12-29-33(5)17-8-16-31(2,3)27(33)15-20-35(29,34)7/h22-30,37-39H,8-21,36H2,1-7H3/t22-,23+,24-,25+,26-,27-,28+,29+,30+,32-,33-,34+,35+/m0/s1

InChI Key

DYJIJIUSBPCLMI-NUJFMENSSA-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
Rhodopseudomonas acidophila	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as bacteriohopanoids. These are bacterial terpenoids structurally characterized by a C30 skeleton, which is usually conjugated to a C5 (usually hydroxylated) unit linked by a carbon-carbon bond.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Hopanoids

Direct Parent

Bacteriohopanoids

Alternative Parents

Substituents

Bacteriohopane skeleton
Sesquaterpenoid
27-hydroxysteroid
25-hydroxysteroid
24-hydroxysteroid
Steroid
1,3-aminoalcohol
1,2-aminoalcohol
Secondary alcohol
Polyol
Organic nitrogen compound
Organonitrogen compound
Primary aliphatic amine
Organooxygen compound
Primary amine
Hydrocarbon derivative
Organopnictogen compound
Amine
Alcohol
Organic oxygen 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

59702300

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

100978430

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Zhang H, Chen Y, Li Y, Song Y, Ma J, Ju J: Secondary Metabolites and Biosynthetic Gene Clusters Analysis of Deep-Sea Hydrothermal Vent-Derived Streptomyces sp. SCSIO ZS0520. Mar Drugs. 2022 Jun 14;20(6):393. doi: 10.3390/md20060393. [PubMed:35736196 ]
Bodlenner A, Liu W, Hirsch G, Schaeffer P, Blumenberg M, Lendt R, Tritsch D, Michaelis W, Rohmer M: C35 Hopanoid Side Chain Biosynthesis: Reduction of Ribosylhopane into Bacteriohopanetetrol by a Cell-Free System Derived from Methylobacterium organophilum. Chembiochem. 2015 Aug 17;16(12):1764-70. doi: 10.1002/cbic.201500021. Epub 2015 Jul 14. [PubMed:26032177 ]
Liu W, Sakr E, Schaeffer P, Talbot HM, Donisi J, Hartner T, Kannenberg E, Takano E, Rohmer M: Ribosylhopane, a novel bacterial hopanoid, as precursor of C35 bacteriohopanepolyols in Streptomyces coelicolor A3(2). Chembiochem. 2014 Sep 22;15(14):2156-61. doi: 10.1002/cbic.201402261. Epub 2014 Aug 22. [PubMed:25155017 ]
Tushar L, Sasikala Ch, Ramana ChV: Draft genome sequence of Rhodomicrobium udaipurense JA643T with special reference to hopanoid biosynthesis. DNA Res. 2014 Dec;21(6):639-47. doi: 10.1093/dnares/dsu026. Epub 2014 Aug 12. [PubMed:25117430 ]
Welander PV, Doughty DM, Wu CH, Mehay S, Summons RE, Newman DK: Identification and characterization of Rhodopseudomonas palustris TIE-1 hopanoid biosynthesis mutants. Geobiology. 2012 Mar;10(2):163-77. doi: 10.1111/j.1472-4669.2011.00314.x. Epub 2012 Jan 4. [PubMed:22221333 ]
LOTUS database [Link]

Showing NP-Card for (2s,3r,4r,7s)-7-[(3r,3as,5ar,5br,7as,11as,11br,13ar,13bs)-5a,5b,8,8,11a,13b-hexamethyl-hexadecahydrocyclopenta[a]chrysen-3-yl]-1-aminooctane-2,3,4-triol (NP0240069)

MOL for NP0240069 ((2s,3r,4r,7s)-7-[(3r,3as,5ar,5br,7as,11as,11br,13ar,13bs)-5a,5b,8,8,11a,13b-hexamethyl-hexadecahydrocyclopenta[a]chrysen-3-yl]-1-aminooctane-2,3,4-triol)

3D MOL for NP0240069 ((2s,3r,4r,7s)-7-[(3r,3as,5ar,5br,7as,11as,11br,13ar,13bs)-5a,5b,8,8,11a,13b-hexamethyl-hexadecahydrocyclopenta[a]chrysen-3-yl]-1-aminooctane-2,3,4-triol)

3D SDF for NP0240069 ((2s,3r,4r,7s)-7-[(3r,3as,5ar,5br,7as,11as,11br,13ar,13bs)-5a,5b,8,8,11a,13b-hexamethyl-hexadecahydrocyclopenta[a]chrysen-3-yl]-1-aminooctane-2,3,4-triol)

3D-SDF for NP0240069 ((2s,3r,4r,7s)-7-[(3r,3as,5ar,5br,7as,11as,11br,13ar,13bs)-5a,5b,8,8,11a,13b-hexamethyl-hexadecahydrocyclopenta[a]chrysen-3-yl]-1-aminooctane-2,3,4-triol)

PDB for NP0240069 ((2s,3r,4r,7s)-7-[(3r,3as,5ar,5br,7as,11as,11br,13ar,13bs)-5a,5b,8,8,11a,13b-hexamethyl-hexadecahydrocyclopenta[a]chrysen-3-yl]-1-aminooctane-2,3,4-triol)

3D PDB for NP0240069 ((2s,3r,4r,7s)-7-[(3r,3as,5ar,5br,7as,11as,11br,13ar,13bs)-5a,5b,8,8,11a,13b-hexamethyl-hexadecahydrocyclopenta[a]chrysen-3-yl]-1-aminooctane-2,3,4-triol)

SMILES for NP0240069 ((2s,3r,4r,7s)-7-[(3r,3as,5ar,5br,7as,11as,11br,13ar,13bs)-5a,5b,8,8,11a,13b-hexamethyl-hexadecahydrocyclopenta[a]chrysen-3-yl]-1-aminooctane-2,3,4-triol)

INCHI for NP0240069 ((2s,3r,4r,7s)-7-[(3r,3as,5ar,5br,7as,11as,11br,13ar,13bs)-5a,5b,8,8,11a,13b-hexamethyl-hexadecahydrocyclopenta[a]chrysen-3-yl]-1-aminooctane-2,3,4-triol)

Structure for NP0240069 ((2s,3r,4r,7s)-7-[(3r,3as,5ar,5br,7as,11as,11br,13ar,13bs)-5a,5b,8,8,11a,13b-hexamethyl-hexadecahydrocyclopenta[a]chrysen-3-yl]-1-aminooctane-2,3,4-triol)

3D Structure for NP0240069 ((2s,3r,4r,7s)-7-[(3r,3as,5ar,5br,7as,11as,11br,13ar,13bs)-5a,5b,8,8,11a,13b-hexamethyl-hexadecahydrocyclopenta[a]chrysen-3-yl]-1-aminooctane-2,3,4-triol)