NP-MRD: Showing NP-Card for (3s,4r,4ar,5r,6as,6br,8ar,10s,12ar,12br,14bs)-2,2,6a,6b,9,9,12a-heptamethyl-4a-({[(2r,3r,4s,5r)-3,4,5-trihydroxyoxan-2-yl]oxy}methyl)-1,3,4,5,6,7,8,8a,10,11,12,12b,13,14b-tetradecahydropicene-3,4,5,10-tetrol (NP0225920)

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Record Information

Version

1.0

Created at

2022-09-06 04:47:40 UTC

Updated at

2022-09-06 04:47:41 UTC

NP-MRD ID

NP0225920

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(3s,4r,4ar,5r,6as,6br,8ar,10s,12ar,12br,14bs)-2,2,6a,6b,9,9,12a-heptamethyl-4a-({[(2r,3r,4s,5r)-3,4,5-trihydroxyoxan-2-yl]oxy}methyl)-1,3,4,5,6,7,8,8a,10,11,12,12b,13,14b-tetradecahydropicene-3,4,5,10-tetrol

Description

(3S,4R,4aR,5R,6aS,6bR,8aR,10S,12aR,12bR,14bS)-2,2,6a,6b,9,9,12a-heptamethyl-4a-({[(2R,3R,4S,5R)-3,4,5-trihydroxyoxan-2-yl]oxy}methyl)-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,12b,13,14b-icosahydropicene-3,4,5,10-tetrol belongs to the class of organic compounds known as triterpenoids. These are terpene molecules containing six isoprene units. (3s,4r,4ar,5r,6as,6br,8ar,10s,12ar,12br,14bs)-2,2,6a,6b,9,9,12a-heptamethyl-4a-({[(2r,3r,4s,5r)-3,4,5-trihydroxyoxan-2-yl]oxy}methyl)-1,3,4,5,6,7,8,8a,10,11,12,12b,13,14b-tetradecahydropicene-3,4,5,10-tetrol is found in Centipeda minima. It was first documented in 2022 (PMID: 36075691). Based on a literature review a significant number of articles have been published on (3S,4R,4aR,5R,6aS,6bR,8aR,10S,12aR,12bR,14bS)-2,2,6a,6b,9,9,12a-heptamethyl-4a-({[(2R,3R,4S,5R)-3,4,5-trihydroxyoxan-2-yl]oxy}methyl)-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,12b,13,14b-icosahydropicene-3,4,5,10-tetrol (PMID: 36075690) (PMID: 36075689) (PMID: 36075688) (PMID: 36075687).

Structure

MOL SDF PDB SMILES InChI


  Mrv1652309062206472D          

 44 49  0  0  1  0            999 V2000
    0.4452   -3.0106    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3020   -3.8230    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4733   -3.5409    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1270   -3.8230    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5395   -4.5375    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.3645   -4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7770   -3.8230    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6020   -3.8230    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0145   -4.5375    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.8395   -4.5375    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.4270   -3.8230    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2520   -3.8230    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0770   -3.8230    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4895   -4.5375    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    7.3145   -4.5375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0770   -5.2520    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9337   -6.0644    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8522   -5.5341    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2520   -5.2520    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.8395   -5.9664    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0145   -5.9664    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6020   -5.2520    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.1895   -5.9664    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7770   -5.2520    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.6907   -6.0725    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  1  0  0  0  0  0  0  0  0  0
    1.1270   -6.6809    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1270   -5.2520    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.7145   -5.9664    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1105   -5.9664    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5230   -6.6809    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.1105   -7.3954    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5230   -8.1099    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3480   -8.1099    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.7605   -8.8243    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7605   -7.3954    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.5855   -7.3954    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3480   -6.6809    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.7605   -5.9664    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3020   -5.2520    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.4517   -5.5875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1105   -4.5375    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.9355   -4.5375    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
  2  4  1  0  0  0  0
  5  4  1  1  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  9  8  1  6  0  0  0
  9 10  1  0  0  0  0
 10 11  1  6  0  0  0
 10 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  6  0  0  0
 14 16  1  0  0  0  0
 16 17  1  0  0  0  0
 16 18  1  0  0  0  0
 16 19  1  0  0  0  0
 10 19  1  0  0  0  0
 19 20  1  6  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
  9 22  1  0  0  0  0
 22 23  1  6  0  0  0
 22 24  1  0  0  0  0
  6 24  1  0  0  0  0
 24 25  1  1  0  0  0
 24 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  1  0  0  0
 27 29  1  0  0  0  0
  5 29  1  0  0  0  0
 29 30  1  6  0  0  0
 30 31  1  0  0  0  0
 32 31  1  6  0  0  0
 32 33  1  0  0  0  0
 33 34  1  0  0  0  0
 34 35  1  0  0  0  0
 35 36  1  1  0  0  0
 35 37  1  0  0  0  0
 37 38  1  6  0  0  0
 37 39  1  0  0  0  0
 32 39  1  0  0  0  0
 39 40  1  1  0  0  0
 29 41  1  0  0  0  0
 41 42  1  1  0  0  0
 41 43  1  0  0  0  0
  2 43  1  0  0  0  0
 43 44  1  1  0  0  0
M  END


  Mrv1652309062206472D          

 44 49  0  0  1  0            999 V2000
    0.4452   -3.0106    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3020   -3.8230    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4733   -3.5409    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1270   -3.8230    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5395   -4.5375    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.3645   -4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7770   -3.8230    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6020   -3.8230    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0145   -4.5375    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.8395   -4.5375    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.4270   -3.8230    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2520   -3.8230    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0770   -3.8230    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4895   -4.5375    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    7.3145   -4.5375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0770   -5.2520    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9337   -6.0644    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8522   -5.5341    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2520   -5.2520    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.8395   -5.9664    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0145   -5.9664    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6020   -5.2520    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.1895   -5.9664    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7770   -5.2520    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.6907   -6.0725    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  1  0  0  0  0  0  0  0  0  0
    1.1270   -6.6809    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1270   -5.2520    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.7145   -5.9664    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1105   -5.9664    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5230   -6.6809    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.1105   -7.3954    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5230   -8.1099    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3480   -8.1099    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.7605   -8.8243    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7605   -7.3954    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.5855   -7.3954    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3480   -6.6809    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.7605   -5.9664    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3020   -5.2520    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.4517   -5.5875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1105   -4.5375    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.9355   -4.5375    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
  2  4  1  0  0  0  0
  5  4  1  1  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  9  8  1  6  0  0  0
  9 10  1  0  0  0  0
 10 11  1  6  0  0  0
 10 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  6  0  0  0
 14 16  1  0  0  0  0
 16 17  1  0  0  0  0
 16 18  1  0  0  0  0
 16 19  1  0  0  0  0
 10 19  1  0  0  0  0
 19 20  1  6  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
  9 22  1  0  0  0  0
 22 23  1  6  0  0  0
 22 24  1  0  0  0  0
  6 24  1  0  0  0  0
 24 25  1  1  0  0  0
 24 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  1  0  0  0
 27 29  1  0  0  0  0
  5 29  1  0  0  0  0
 29 30  1  6  0  0  0
 30 31  1  0  0  0  0
 32 31  1  6  0  0  0
 32 33  1  0  0  0  0
 33 34  1  0  0  0  0
 34 35  1  0  0  0  0
 35 36  1  1  0  0  0
 35 37  1  0  0  0  0
 37 38  1  6  0  0  0
 37 39  1  0  0  0  0
 32 39  1  0  0  0  0
 39 40  1  1  0  0  0
 29 41  1  0  0  0  0
 41 42  1  1  0  0  0
 41 43  1  0  0  0  0
  2 43  1  0  0  0  0
 43 44  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0225920

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1(C)C[C@H]2C3=CC[C@@H]4[C@@]5(C)CC[C@H](O)C(C)(C)[C@@H]5CC[C@@]4(C)[C@]3(C)C[C@@H](O)[C@@]2(CO[C@@H]2OC[C@@H](O)[C@H](O)[C@H]2O)[C@@H](O)[C@H]1O

> <INCHI_IDENTIFIER>
InChI=1S/C35H58O9/c1-30(2)14-19-18-8-9-22-32(5)12-11-23(37)31(3,4)21(32)10-13-33(22,6)34(18,7)15-24(38)35(19,28(42)27(30)41)17-44-29-26(40)25(39)20(36)16-43-29/h8,19-29,36-42H,9-17H2,1-7H3/t19-,20+,21-,22+,23-,24+,25-,26+,27+,28-,29-,32-,33+,34+,35-/m0/s1

> <INCHI_KEY>
NKGUYFRENWXBSE-OREUGHDZSA-N

> <FORMULA>
C35H58O9

> <MOLECULAR_WEIGHT>
622.84

> <EXACT_MASS>
622.408083448

> <JCHEM_ACCEPTOR_COUNT>
9

> <JCHEM_ATOM_COUNT>
102

> <JCHEM_AVERAGE_POLARIZABILITY>
70.35939792296958

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
7

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(3S,4R,4aR,5R,6aS,6bR,8aR,10S,12aR,12bR,14bS)-2,2,6a,6b,9,9,12a-heptamethyl-4a-({[(2R,3R,4S,5R)-3,4,5-trihydroxyoxan-2-yl]oxy}methyl)-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,12b,13,14b-icosahydropicene-3,4,5,10-tetrol

> <JCHEM_LOGP>
1.6012506929999986

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.095595007395751

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.212053167923454

> <JCHEM_PKA_STRONGEST_BASIC>
-0.8349864376871968

> <JCHEM_POLAR_SURFACE_AREA>
160.07

> <JCHEM_REFRACTIVITY>
164.37130000000005

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(3S,4R,4aR,5R,6aS,6bR,8aR,10S,12aR,12bR,14bS)-2,2,6a,6b,9,9,12a-heptamethyl-4a-({[(2R,3R,4S,5R)-3,4,5-trihydroxyoxan-2-yl]oxy}methyl)-1,3,4,5,6,7,8,8a,10,11,12,12b,13,14b-tetradecahydropicene-3,4,5,10-tetrol

> <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       0.831  -5.620   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.564  -7.136   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -0.883  -6.610   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.104  -7.136   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.874  -8.470   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.414  -8.470   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       5.184  -7.136   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       6.724  -7.136   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       7.494  -8.470   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       9.034  -8.470   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       8.264  -7.136   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       9.804  -7.136   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      11.344  -7.136   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      12.114  -8.470   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      13.654  -8.470   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0      11.344  -9.804   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      11.076 -11.320   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      12.791 -10.330   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       9.804  -9.804   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       9.034 -11.137   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       7.494 -11.137   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       6.724  -9.804   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       5.954 -11.137   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       5.184  -9.804   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       5.023 -11.335   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       4.414 -11.137   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       2.874 -11.137   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0       2.104 -12.471   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0       2.104  -9.804   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       1.334 -11.137   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0      -0.206 -11.137   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0      -0.976 -12.471   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0      -0.206 -13.805   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0      -0.976 -15.138   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      -2.516 -15.138   0.000  0.00  0.00           C+0
HETATM   36  O   UNK     0      -3.286 -16.472   0.000  0.00  0.00           O+0
HETATM   37  C   UNK     0      -3.286 -13.805   0.000  0.00  0.00           C+0
HETATM   38  O   UNK     0      -4.826 -13.805   0.000  0.00  0.00           O+0
HETATM   39  C   UNK     0      -2.516 -12.471   0.000  0.00  0.00           C+0
HETATM   40  O   UNK     0      -3.286 -11.137   0.000  0.00  0.00           O+0
HETATM   41  C   UNK     0       0.564  -9.804   0.000  0.00  0.00           C+0
HETATM   42  O   UNK     0      -0.843 -10.430   0.000  0.00  0.00           O+0
HETATM   43  C   UNK     0      -0.206  -8.470   0.000  0.00  0.00           C+0
HETATM   44  O   UNK     0      -1.746  -8.470   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    4   43                                             
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6   29                                                  
CONECT    6    5    7   24                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   22                                                  
CONECT   10    9   11   12   19                                             
CONECT   11   10                                                            
CONECT   12   10   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14   17   18   19                                             
CONECT   17   16                                                            
CONECT   18   16                                                            
CONECT   19   16   10   20                                                  
CONECT   20   19   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21    9   23   24                                             
CONECT   23   22                                                            
CONECT   24   22    6   25   26                                             
CONECT   25   24                                                            
CONECT   26   24   27                                                       
CONECT   27   26   28   29                                                  
CONECT   28   27                                                            
CONECT   29   27    5   30   41                                             
CONECT   30   29   31                                                       
CONECT   31   30   32                                                       
CONECT   32   31   33   39                                                  
CONECT   33   32   34                                                       
CONECT   34   33   35                                                       
CONECT   35   34   36   37                                                  
CONECT   36   35                                                            
CONECT   37   35   38   39                                                  
CONECT   38   37                                                            
CONECT   39   37   32   40                                                  
CONECT   40   39                                                            
CONECT   41   29   42   43                                                  
CONECT   42   41                                                            
CONECT   43   41    2   44                                                  
CONECT   44   43                                                            
MASTER        0    0    0    0    0    0    0    0   44    0   98    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₃₅H₅₈O₉

Average Mass

622.8400 Da

Monoisotopic Mass

622.40808 Da

IUPAC Name

Traditional Name

(3S,4R,4aR,5R,6aS,6bR,8aR,10S,12aR,12bR,14bS)-2,2,6a,6b,9,9,12a-heptamethyl-4a-({[(2R,3R,4S,5R)-3,4,5-trihydroxyoxan-2-yl]oxy}methyl)-1,3,4,5,6,7,8,8a,10,11,12,12b,13,14b-tetradecahydropicene-3,4,5,10-tetrol

CAS Registry Number

Not Available

SMILES

CC1(C)C[C@H]2C3=CC[C@@H]4[C@@]5(C)CC[C@H](O)C(C)(C)[C@@H]5CC[C@@]4(C)[C@]3(C)C[C@@H](O)[C@@]2(CO[C@@H]2OC[C@@H](O)[C@H](O)[C@H]2O)[C@@H](O)[C@H]1O

InChI Identifier

InChI=1S/C35H58O9/c1-30(2)14-19-18-8-9-22-32(5)12-11-23(37)31(3,4)21(32)10-13-33(22,6)34(18,7)15-24(38)35(19,28(42)27(30)41)17-44-29-26(40)25(39)20(36)16-43-29/h8,19-29,36-42H,9-17H2,1-7H3/t19-,20+,21-,22+,23-,24+,25-,26+,27+,28-,29-,32-,33+,34+,35-/m0/s1

InChI Key

NKGUYFRENWXBSE-OREUGHDZSA-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
Centipeda minima	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as triterpenoids. These are terpene molecules containing six isoprene units.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Triterpenoids

Direct Parent

Triterpenoids

Alternative Parents

Substituents

Triterpenoid
Glycosyl compound
O-glycosyl compound
Monosaccharide
Oxane
Cyclic alcohol
Secondary alcohol
Polyol
Acetal
Oxacycle
Organoheterocyclic compound
Alcohol
Organooxygen compound
Hydrocarbon derivative
Organic oxygen compound
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic 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	1.6	ChemAxon
pKa (Strongest Acidic)	12.21	ChemAxon
pKa (Strongest Basic)	-0.83	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	9	ChemAxon
Hydrogen Donor Count	7	ChemAxon
Polar Surface Area	160.07 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	164.37 m³·mol⁻¹	ChemAxon
Polarizability	70.36 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	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

163033221

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Abioye AI, Sudfeld CR, Hughes MD, Aboud S, Muhihi A, Ulenga N, Nagu TJ, Wang M, Mugusi F, Fawzi WW: Iron status among HIV-infected adults during the first year of antiretroviral therapy in Tanzania. HIV Med. 2022 Sep 8. doi: 10.1111/hiv.13396. [PubMed:36075691 ]
Authors unspecified: Resources Round-up. Altern Lab Anim. 2022 Sep 8:2611929221121256. doi: 10.1177/02611929221121256. [PubMed:36075690 ]
Kim JU, Khan W, Arowoshola L, Ahmad M: Correspondence. Eur Heart J Qual Care Clin Outcomes. 2022 Aug 26. pii: 6677390. doi: 10.1093/ehjqcco/qcac051. [PubMed:36075689 ]
DaVault L: Field Amputations Facilitated by a Surgical Extraction Team. Am Surg. 2022 Sep 8:31348221114521. doi: 10.1177/00031348221114521. [PubMed:36075688 ]
Szanyi J, Walles JK, Tesfaye F, Gudeta AN, Bjorkman P: Intrauterine HIV exposure is associated with linear growth restriction among Ethiopian children in the first 18 months of life. Trop Med Int Health. 2022 Sep;27(9):823-830. doi: 10.1111/tmi.13805. Epub 2022 Aug 17. [PubMed:36075687 ]
LOTUS database [Link]

Showing NP-Card for (3s,4r,4ar,5r,6as,6br,8ar,10s,12ar,12br,14bs)-2,2,6a,6b,9,9,12a-heptamethyl-4a-({[(2r,3r,4s,5r)-3,4,5-trihydroxyoxan-2-yl]oxy}methyl)-1,3,4,5,6,7,8,8a,10,11,12,12b,13,14b-tetradecahydropicene-3,4,5,10-tetrol (NP0225920)

MOL for NP0225920 ((3s,4r,4ar,5r,6as,6br,8ar,10s,12ar,12br,14bs)-2,2,6a,6b,9,9,12a-heptamethyl-4a-({[(2r,3r,4s,5r)-3,4,5-trihydroxyoxan-2-yl]oxy}methyl)-1,3,4,5,6,7,8,8a,10,11,12,12b,13,14b-tetradecahydropicene-3,4,5,10-tetrol)

3D MOL for NP0225920 ((3s,4r,4ar,5r,6as,6br,8ar,10s,12ar,12br,14bs)-2,2,6a,6b,9,9,12a-heptamethyl-4a-({[(2r,3r,4s,5r)-3,4,5-trihydroxyoxan-2-yl]oxy}methyl)-1,3,4,5,6,7,8,8a,10,11,12,12b,13,14b-tetradecahydropicene-3,4,5,10-tetrol)

3D SDF for NP0225920 ((3s,4r,4ar,5r,6as,6br,8ar,10s,12ar,12br,14bs)-2,2,6a,6b,9,9,12a-heptamethyl-4a-({[(2r,3r,4s,5r)-3,4,5-trihydroxyoxan-2-yl]oxy}methyl)-1,3,4,5,6,7,8,8a,10,11,12,12b,13,14b-tetradecahydropicene-3,4,5,10-tetrol)

3D-SDF for NP0225920 ((3s,4r,4ar,5r,6as,6br,8ar,10s,12ar,12br,14bs)-2,2,6a,6b,9,9,12a-heptamethyl-4a-({[(2r,3r,4s,5r)-3,4,5-trihydroxyoxan-2-yl]oxy}methyl)-1,3,4,5,6,7,8,8a,10,11,12,12b,13,14b-tetradecahydropicene-3,4,5,10-tetrol)

PDB for NP0225920 ((3s,4r,4ar,5r,6as,6br,8ar,10s,12ar,12br,14bs)-2,2,6a,6b,9,9,12a-heptamethyl-4a-({[(2r,3r,4s,5r)-3,4,5-trihydroxyoxan-2-yl]oxy}methyl)-1,3,4,5,6,7,8,8a,10,11,12,12b,13,14b-tetradecahydropicene-3,4,5,10-tetrol)

3D PDB for NP0225920 ((3s,4r,4ar,5r,6as,6br,8ar,10s,12ar,12br,14bs)-2,2,6a,6b,9,9,12a-heptamethyl-4a-({[(2r,3r,4s,5r)-3,4,5-trihydroxyoxan-2-yl]oxy}methyl)-1,3,4,5,6,7,8,8a,10,11,12,12b,13,14b-tetradecahydropicene-3,4,5,10-tetrol)

SMILES for NP0225920 ((3s,4r,4ar,5r,6as,6br,8ar,10s,12ar,12br,14bs)-2,2,6a,6b,9,9,12a-heptamethyl-4a-({[(2r,3r,4s,5r)-3,4,5-trihydroxyoxan-2-yl]oxy}methyl)-1,3,4,5,6,7,8,8a,10,11,12,12b,13,14b-tetradecahydropicene-3,4,5,10-tetrol)

INCHI for NP0225920 ((3s,4r,4ar,5r,6as,6br,8ar,10s,12ar,12br,14bs)-2,2,6a,6b,9,9,12a-heptamethyl-4a-({[(2r,3r,4s,5r)-3,4,5-trihydroxyoxan-2-yl]oxy}methyl)-1,3,4,5,6,7,8,8a,10,11,12,12b,13,14b-tetradecahydropicene-3,4,5,10-tetrol)

Structure for NP0225920 ((3s,4r,4ar,5r,6as,6br,8ar,10s,12ar,12br,14bs)-2,2,6a,6b,9,9,12a-heptamethyl-4a-({[(2r,3r,4s,5r)-3,4,5-trihydroxyoxan-2-yl]oxy}methyl)-1,3,4,5,6,7,8,8a,10,11,12,12b,13,14b-tetradecahydropicene-3,4,5,10-tetrol)

3D Structure for NP0225920 ((3s,4r,4ar,5r,6as,6br,8ar,10s,12ar,12br,14bs)-2,2,6a,6b,9,9,12a-heptamethyl-4a-({[(2r,3r,4s,5r)-3,4,5-trihydroxyoxan-2-yl]oxy}methyl)-1,3,4,5,6,7,8,8a,10,11,12,12b,13,14b-tetradecahydropicene-3,4,5,10-tetrol)