NP-MRD: Showing NP-Card for 5-({7-[(3r,5ar,5br,9s,11as,13bs)-5a,5b,8,8,9,11a,13b-heptamethyl-1h,2h,3h,3ah,4h,5h,6h,7h,7ah,9h,10h,11h,11bh,13ah-cyclopenta[a]chrysen-3-yl]-2,3,4-trihydroxy-5-methyloctyl}oxy)-4-amino-1-(hydroxymethyl)cyclopentane-1,2,3-triol (NP0222642)

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Record Information

Version

2.0

Created at

2022-09-06 00:31:51 UTC

Updated at

2022-09-06 00:31:52 UTC

NP-MRD ID

NP0222642

Secondary Accession Numbers

None

Natural Product Identification

Common Name

5-({7-[(3r,5ar,5br,9s,11as,13bs)-5a,5b,8,8,9,11a,13b-heptamethyl-1h,2h,3h,3ah,4h,5h,6h,7h,7ah,9h,10h,11h,11bh,13ah-cyclopenta[a]chrysen-3-yl]-2,3,4-trihydroxy-5-methyloctyl}oxy)-4-amino-1-(hydroxymethyl)cyclopentane-1,2,3-triol

Description

4-Amino-5-({7-[(1R,2R,6R,9S,14S,17S)-1,2,9,14,17,18,18-heptamethylpentacyclo[11.8.0.0²,¹⁰.0⁵,⁹.0¹⁴,¹⁹]Henicos-11-en-6-yl]-2,3,4-trihydroxy-5-methyloctyl}oxy)-1-(hydroxymethyl)cyclopentane-1,2,3-triol 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 4-amino-5-({7-[(1R,2R,6R,9S,14S,17S)-1,2,9,14,17,18,18-heptamethylpentacyclo[11.8.0.0²,¹⁰.0⁵,⁹.0¹⁴,¹⁹]Henicos-11-en-6-yl]-2,3,4-trihydroxy-5-methyloctyl}oxy)-1-(hydroxymethyl)cyclopentane-1,2,3-triol.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652309062202312D          

 52 57  0  0  1  0            999 V2000
    3.3309   -6.6110    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3309   -5.7860    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6164   -5.3735    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9019   -5.7860    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9019   -6.6110    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1875   -5.3735    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.4338   -5.7091    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1182   -5.0960    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2943   -4.3815    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.5262   -4.2953    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1012   -4.5531    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6533   -3.9400    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3983   -3.1553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5914   -2.9838    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.1434   -2.3707    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0393   -3.5969    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7676   -3.4254    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0226   -2.6408    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4705   -2.0277    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7255   -1.2430    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.2775   -1.8561    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5325   -1.0715    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7874   -0.2869    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2354    0.3262    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.4903    1.1108    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4284    0.1547    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3996    0.9792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3886    0.2695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1735   -0.6300    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6335   -0.8015    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8885   -1.5861    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3364   -2.1992    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.0901   -1.8636    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0454   -5.3735    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0454   -4.5485    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7598   -5.7860    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7598   -6.6110    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4743   -5.3735    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4743   -4.5485    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1888   -5.7860    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9032   -5.3735    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.6177   -5.7860    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3714   -5.4505    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5429   -4.6435    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.9234   -6.0636    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7439   -5.9773    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.5109   -6.7780    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8465   -7.5317    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.7040   -6.6065    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4408   -7.3884    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.8988   -6.7865    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6521   -7.5737    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  6  4  1  1  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  1  0  0  0
  9 11  1  0  0  0  0
  6 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
 14 15  1  1  0  0  0
 14 16  1  0  0  0  0
  9 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  6  0  0  0
 20 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  6  0  0  0
 24 26  1  0  0  0  0
 26 27  1  0  0  0  0
 26 28  1  0  0  0  0
 26 29  1  0  0  0  0
 20 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
 19 32  1  0  0  0  0
 14 32  1  0  0  0  0
 32 33  1  6  0  0  0
  2 34  1  0  0  0  0
 34 35  1  0  0  0  0
 34 36  1  0  0  0  0
 36 37  1  0  0  0  0
 36 38  1  0  0  0  0
 38 39  1  0  0  0  0
 38 40  1  0  0  0  0
 40 41  1  0  0  0  0
 41 42  1  0  0  0  0
 42 43  1  0  0  0  0
 43 44  1  0  0  0  0
 43 45  1  0  0  0  0
 45 46  1  0  0  0  0
 45 47  1  0  0  0  0
 47 48  1  0  0  0  0
 47 49  1  0  0  0  0
 42 49  1  0  0  0  0
 49 50  1  0  0  0  0
 49 51  1  0  0  0  0
 51 52  1  0  0  0  0
M  END


  Mrv1652309062202312D          

 52 57  0  0  1  0            999 V2000
    3.3309   -6.6110    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3309   -5.7860    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6164   -5.3735    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9019   -5.7860    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9019   -6.6110    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1875   -5.3735    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.4338   -5.7091    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1182   -5.0960    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2943   -4.3815    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.5262   -4.2953    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1012   -4.5531    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6533   -3.9400    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3983   -3.1553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5914   -2.9838    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.1434   -2.3707    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0393   -3.5969    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7676   -3.4254    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0226   -2.6408    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4705   -2.0277    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7255   -1.2430    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.2775   -1.8561    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5325   -1.0715    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7874   -0.2869    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2354    0.3262    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.4903    1.1108    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4284    0.1547    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3996    0.9792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3886    0.2695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1735   -0.6300    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6335   -0.8015    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8885   -1.5861    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3364   -2.1992    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.0901   -1.8636    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0454   -5.3735    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0454   -4.5485    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7598   -5.7860    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7598   -6.6110    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4743   -5.3735    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4743   -4.5485    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1888   -5.7860    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9032   -5.3735    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.6177   -5.7860    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3714   -5.4505    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5429   -4.6435    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.9234   -6.0636    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7439   -5.9773    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.5109   -6.7780    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8465   -7.5317    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.7040   -6.6065    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4408   -7.3884    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.8988   -6.7865    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6521   -7.5737    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  6  4  1  1  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  1  0  0  0
  9 11  1  0  0  0  0
  6 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
 14 15  1  1  0  0  0
 14 16  1  0  0  0  0
  9 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  6  0  0  0
 20 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  6  0  0  0
 24 26  1  0  0  0  0
 26 27  1  0  0  0  0
 26 28  1  0  0  0  0
 26 29  1  0  0  0  0
 20 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
 19 32  1  0  0  0  0
 14 32  1  0  0  0  0
 32 33  1  6  0  0  0
  2 34  1  0  0  0  0
 34 35  1  0  0  0  0
 34 36  1  0  0  0  0
 36 37  1  0  0  0  0
 36 38  1  0  0  0  0
 38 39  1  0  0  0  0
 38 40  1  0  0  0  0
 40 41  1  0  0  0  0
 41 42  1  0  0  0  0
 42 43  1  0  0  0  0
 43 44  1  0  0  0  0
 43 45  1  0  0  0  0
 45 46  1  0  0  0  0
 45 47  1  0  0  0  0
 47 48  1  0  0  0  0
 47 49  1  0  0  0  0
 42 49  1  0  0  0  0
 49 50  1  0  0  0  0
 49 51  1  0  0  0  0
 51 52  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0222642

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(CC(C)[C@H]1CC[C@@]2(C)C1CC[C@]1(C)C2C=CC2[C@@]3(C)CC[C@H](C)C(C)(C)C3CC[C@@]12C)C(O)C(O)C(O)COC1C(N)C(O)C(O)C1(O)CO

> <INCHI_IDENTIFIER>
InChI=1S/C43H75NO8/c1-23(20-24(2)33(47)34(48)28(46)21-52-37-32(44)35(49)36(50)43(37,51)22-45)26-13-17-39(6)27(26)14-18-41(8)30(39)10-11-31-40(7)16-12-25(3)38(4,5)29(40)15-19-42(31,41)9/h10-11,23-37,45-51H,12-22,44H2,1-9H3/t23?,24?,25-,26+,27?,28?,29?,30?,31?,32?,33?,34?,35?,36?,37?,39-,40-,41+,42+,43?/m0/s1

> <INCHI_KEY>
WNPSYLUYXAXQSP-VLYGMAJHSA-N

> <FORMULA>
C43H75NO8

> <MOLECULAR_WEIGHT>
734.072

> <EXACT_MASS>
733.549268379

> <JCHEM_ACCEPTOR_COUNT>
9

> <JCHEM_ATOM_COUNT>
127

> <JCHEM_AVERAGE_POLARIZABILITY>
87.32107698841611

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
8

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
4-amino-5-({7-[(1R,2R,6R,9S,14S,17S)-1,2,9,14,17,18,18-heptamethylpentacyclo[11.8.0.0^{2,10}.0^{5,9}.0^{14,19}]henicos-11-en-6-yl]-2,3,4-trihydroxy-5-methyloctyl}oxy)-1-(hydroxymethyl)cyclopentane-1,2,3-triol

> <JCHEM_LOGP>
4.014841279666665

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
12.81052299748238

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.923720181574636

> <JCHEM_PKA_STRONGEST_BASIC>
8.165075158024555

> <JCHEM_POLAR_SURFACE_AREA>
176.85999999999999

> <JCHEM_REFRACTIVITY>
202.91210000000004

> <JCHEM_ROTATABLE_BOND_COUNT>
10

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
4-amino-5-({7-[(1R,2R,6R,9S,14S,17S)-1,2,9,14,17,18,18-heptamethylpentacyclo[11.8.0.0^{2,10}.0^{5,9}.0^{14,19}]henicos-11-en-6-yl]-2,3,4-trihydroxy-5-methyloctyl}oxy)-1-(hydroxymethyl)cyclopentane-1,2,3-triol

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 06-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-SEP-22         0                                  
HETATM    1  C   UNK     0       6.218 -12.341   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       6.218 -10.801   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       4.884 -10.031   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       3.550 -10.801   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       3.550 -12.341   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.217 -10.031   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.810 -10.657   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -0.221  -9.513   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.549  -8.179   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -0.982  -8.018   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.056  -8.499   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       3.086  -7.355   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       2.610  -5.890   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       1.104  -5.570   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       2.134  -4.425   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       0.073  -6.714   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -1.433  -6.394   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -1.909  -4.929   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -0.878  -3.785   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -1.354  -2.320   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -2.385  -3.465   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -2.861  -2.000   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -3.336  -0.536   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      -2.306   0.609   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      -2.782   2.074   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      -0.800   0.289   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      -0.746   1.828   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       0.725   0.503   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      -0.324  -1.176   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       1.183  -1.496   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       1.658  -2.961   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       0.628  -4.105   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       2.035  -3.479   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       7.551 -10.031   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0       7.551  -8.491   0.000  0.00  0.00           O+0
HETATM   36  C   UNK     0       8.885 -10.801   0.000  0.00  0.00           C+0
HETATM   37  O   UNK     0       8.885 -12.341   0.000  0.00  0.00           O+0
HETATM   38  C   UNK     0      10.219 -10.031   0.000  0.00  0.00           C+0
HETATM   39  O   UNK     0      10.219  -8.491   0.000  0.00  0.00           O+0
HETATM   40  C   UNK     0      11.552 -10.801   0.000  0.00  0.00           C+0
HETATM   41  O   UNK     0      12.886 -10.031   0.000  0.00  0.00           O+0
HETATM   42  C   UNK     0      14.220 -10.801   0.000  0.00  0.00           C+0
HETATM   43  C   UNK     0      15.627 -10.174   0.000  0.00  0.00           C+0
HETATM   44  N   UNK     0      15.947  -8.668   0.000  0.00  0.00           N+0
HETATM   45  C   UNK     0      16.657 -11.319   0.000  0.00  0.00           C+0
HETATM   46  O   UNK     0      18.189 -11.158   0.000  0.00  0.00           O+0
HETATM   47  C   UNK     0      15.887 -12.652   0.000  0.00  0.00           C+0
HETATM   48  O   UNK     0      16.513 -14.059   0.000  0.00  0.00           O+0
HETATM   49  C   UNK     0      14.381 -12.332   0.000  0.00  0.00           C+0
HETATM   50  O   UNK     0      13.890 -13.792   0.000  0.00  0.00           O+0
HETATM   51  C   UNK     0      12.878 -12.668   0.000  0.00  0.00           C+0
HETATM   52  O   UNK     0      12.417 -14.138   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   34                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7   11                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   11   16                                             
CONECT   10    9                                                            
CONECT   11    9    6   12                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15   16   32                                             
CONECT   15   14                                                            
CONECT   16   14    9   17                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20   32                                                  
CONECT   20   19   21   22   29                                             
CONECT   21   20                                                            
CONECT   22   20   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23   25   26                                                  
CONECT   25   24                                                            
CONECT   26   24   27   28   29                                             
CONECT   27   26                                                            
CONECT   28   26                                                            
CONECT   29   26   20   30                                                  
CONECT   30   29   31                                                       
CONECT   31   30   32                                                       
CONECT   32   31   19   14   33                                             
CONECT   33   32                                                            
CONECT   34    2   35   36                                                  
CONECT   35   34                                                            
CONECT   36   34   37   38                                                  
CONECT   37   36                                                            
CONECT   38   36   39   40                                                  
CONECT   39   38                                                            
CONECT   40   38   41                                                       
CONECT   41   40   42                                                       
CONECT   42   41   43   49                                                  
CONECT   43   42   44   45                                                  
CONECT   44   43                                                            
CONECT   45   43   46   47                                                  
CONECT   46   45                                                            
CONECT   47   45   48   49                                                  
CONECT   48   47                                                            
CONECT   49   47   42   50   51                                             
CONECT   50   49                                                            
CONECT   51   49   52                                                       
CONECT   52   51                                                            
MASTER        0    0    0    0    0    0    0    0   52    0  114    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₄₃H₇₅NO₈

Average Mass

734.0720 Da

Monoisotopic Mass

733.54927 Da

IUPAC Name

4-amino-5-({7-[(1R,2R,6R,9S,14S,17S)-1,2,9,14,17,18,18-heptamethylpentacyclo[11.8.0.0^{2,10}.0^{5,9}.0^{14,19}]henicos-11-en-6-yl]-2,3,4-trihydroxy-5-methyloctyl}oxy)-1-(hydroxymethyl)cyclopentane-1,2,3-triol

Traditional Name

CAS Registry Number

Not Available

SMILES

CC(CC(C)[C@H]1CC[C@@]2(C)C1CC[C@]1(C)C2C=CC2[C@@]3(C)CC[C@H](C)C(C)(C)C3CC[C@@]12C)C(O)C(O)C(O)COC1C(N)C(O)C(O)C1(O)CO

InChI Identifier

InChI=1S/C43H75NO8/c1-23(20-24(2)33(47)34(48)28(46)21-52-37-32(44)35(49)36(50)43(37,51)22-45)26-13-17-39(6)27(26)14-18-41(8)30(39)10-11-31-40(7)16-12-25(3)38(4,5)29(40)15-19-42(31,41)9/h10-11,23-37,45-51H,12-22,44H2,1-9H3/t23?,24?,25-,26+,27?,28?,29?,30?,31?,32?,33?,34?,35?,36?,37?,39-,40-,41+,42+,43?/m0/s1

InChI Key

WNPSYLUYXAXQSP-VLYGMAJHSA-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

Hopane-skeleton
Triterpenoid
27-hydroxysteroid
25-hydroxysteroid
24-hydroxysteroid
Steroid
Pentose monosaccharide
Aminocyclitol or derivatives
Aminocyclitol
Cyclitol or derivatives
Cyclopentanol
Monosaccharide
Cyclic alcohol
Tertiary alcohol
Secondary alcohol
1,2-aminoalcohol
Polyol
Dialkyl ether
Ether
Organopnictogen compound
Organic oxygen compound
Primary amine
Primary alcohol
Alcohol
Organonitrogen compound
Organooxygen compound
Organic nitrogen compound
Amine
Hydrocarbon derivative
Primary aliphatic amine
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	4.01	ChemAxon
pKa (Strongest Acidic)	11.92	ChemAxon
pKa (Strongest Basic)	8.17	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	9	ChemAxon
Hydrogen Donor Count	8	ChemAxon
Polar Surface Area	176.86 Å²	ChemAxon
Rotatable Bond Count	10	ChemAxon
Refractivity	202.91 m³·mol⁻¹	ChemAxon
Polarizability	87.32 Å³	ChemAxon
Number of Rings	6	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	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

78445359

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

139588630

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 5-({7-[(3r,5ar,5br,9s,11as,13bs)-5a,5b,8,8,9,11a,13b-heptamethyl-1h,2h,3h,3ah,4h,5h,6h,7h,7ah,9h,10h,11h,11bh,13ah-cyclopenta[a]chrysen-3-yl]-2,3,4-trihydroxy-5-methyloctyl}oxy)-4-amino-1-(hydroxymethyl)cyclopentane-1,2,3-triol (NP0222642)

MOL for NP0222642 (5-({7-[(3r,5ar,5br,9s,11as,13bs)-5a,5b,8,8,9,11a,13b-heptamethyl-1h,2h,3h,3ah,4h,5h,6h,7h,7ah,9h,10h,11h,11bh,13ah-cyclopenta[a]chrysen-3-yl]-2,3,4-trihydroxy-5-methyloctyl}oxy)-4-amino-1-(hydroxymethyl)cyclopentane-1,2,3-triol)

3D MOL for NP0222642 (5-({7-[(3r,5ar,5br,9s,11as,13bs)-5a,5b,8,8,9,11a,13b-heptamethyl-1h,2h,3h,3ah,4h,5h,6h,7h,7ah,9h,10h,11h,11bh,13ah-cyclopenta[a]chrysen-3-yl]-2,3,4-trihydroxy-5-methyloctyl}oxy)-4-amino-1-(hydroxymethyl)cyclopentane-1,2,3-triol)

3D SDF for NP0222642 (5-({7-[(3r,5ar,5br,9s,11as,13bs)-5a,5b,8,8,9,11a,13b-heptamethyl-1h,2h,3h,3ah,4h,5h,6h,7h,7ah,9h,10h,11h,11bh,13ah-cyclopenta[a]chrysen-3-yl]-2,3,4-trihydroxy-5-methyloctyl}oxy)-4-amino-1-(hydroxymethyl)cyclopentane-1,2,3-triol)

3D-SDF for NP0222642 (5-({7-[(3r,5ar,5br,9s,11as,13bs)-5a,5b,8,8,9,11a,13b-heptamethyl-1h,2h,3h,3ah,4h,5h,6h,7h,7ah,9h,10h,11h,11bh,13ah-cyclopenta[a]chrysen-3-yl]-2,3,4-trihydroxy-5-methyloctyl}oxy)-4-amino-1-(hydroxymethyl)cyclopentane-1,2,3-triol)

PDB for NP0222642 (5-({7-[(3r,5ar,5br,9s,11as,13bs)-5a,5b,8,8,9,11a,13b-heptamethyl-1h,2h,3h,3ah,4h,5h,6h,7h,7ah,9h,10h,11h,11bh,13ah-cyclopenta[a]chrysen-3-yl]-2,3,4-trihydroxy-5-methyloctyl}oxy)-4-amino-1-(hydroxymethyl)cyclopentane-1,2,3-triol)

3D PDB for NP0222642 (5-({7-[(3r,5ar,5br,9s,11as,13bs)-5a,5b,8,8,9,11a,13b-heptamethyl-1h,2h,3h,3ah,4h,5h,6h,7h,7ah,9h,10h,11h,11bh,13ah-cyclopenta[a]chrysen-3-yl]-2,3,4-trihydroxy-5-methyloctyl}oxy)-4-amino-1-(hydroxymethyl)cyclopentane-1,2,3-triol)

SMILES for NP0222642 (5-({7-[(3r,5ar,5br,9s,11as,13bs)-5a,5b,8,8,9,11a,13b-heptamethyl-1h,2h,3h,3ah,4h,5h,6h,7h,7ah,9h,10h,11h,11bh,13ah-cyclopenta[a]chrysen-3-yl]-2,3,4-trihydroxy-5-methyloctyl}oxy)-4-amino-1-(hydroxymethyl)cyclopentane-1,2,3-triol)

INCHI for NP0222642 (5-({7-[(3r,5ar,5br,9s,11as,13bs)-5a,5b,8,8,9,11a,13b-heptamethyl-1h,2h,3h,3ah,4h,5h,6h,7h,7ah,9h,10h,11h,11bh,13ah-cyclopenta[a]chrysen-3-yl]-2,3,4-trihydroxy-5-methyloctyl}oxy)-4-amino-1-(hydroxymethyl)cyclopentane-1,2,3-triol)

Structure for NP0222642 (5-({7-[(3r,5ar,5br,9s,11as,13bs)-5a,5b,8,8,9,11a,13b-heptamethyl-1h,2h,3h,3ah,4h,5h,6h,7h,7ah,9h,10h,11h,11bh,13ah-cyclopenta[a]chrysen-3-yl]-2,3,4-trihydroxy-5-methyloctyl}oxy)-4-amino-1-(hydroxymethyl)cyclopentane-1,2,3-triol)

3D Structure for NP0222642 (5-({7-[(3r,5ar,5br,9s,11as,13bs)-5a,5b,8,8,9,11a,13b-heptamethyl-1h,2h,3h,3ah,4h,5h,6h,7h,7ah,9h,10h,11h,11bh,13ah-cyclopenta[a]chrysen-3-yl]-2,3,4-trihydroxy-5-methyloctyl}oxy)-4-amino-1-(hydroxymethyl)cyclopentane-1,2,3-triol)