NP-MRD: Showing NP-Card for (+)-Mudanpinoic acid A (NP0082861)

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Record Information

Version

2.0

Created at

2022-04-29 03:56:28 UTC

Updated at

2022-04-29 03:56:29 UTC

NP-MRD ID

NP0082861

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(+)-Mudanpinoic acid A

Description

(1S,3R,5R,6R,9S,11R,14R,18S,23R)-9-hydroxy-6,10,10,14,21,21-hexamethylhexacyclo[13.8.0.0¹,³.0⁵,¹⁴.0⁶,¹¹.0¹⁸,²³]Tricos-15-ene-18-carboxylic acid belongs to the class of organic compounds known as cyclic alcohols and derivatives. These are organic compounds containing an aliphatic ring substituted with at least one hydroxyl group. (+)-Mudanpinoic acid A is found in Paeonia suffruticosa . Based on a literature review very few articles have been published on (1S,3R,5R,6R,9S,11R,14R,18S,23R)-9-hydroxy-6,10,10,14,21,21-hexamethylhexacyclo[13.8.0.0¹,³.0⁵,¹⁴.0⁶,¹¹.0¹⁸,²³]Tricos-15-ene-18-carboxylic acid.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652304292205562D          

 33 38  0  0  1  0            999 V2000
    1.1270   -1.3480    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.5395   -2.0625    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.1270   -2.7770    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3020   -2.7770    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1105   -2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3020   -1.3480    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2732   -3.6015    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3977   -3.2142    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645   -2.0625    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.7770   -1.3480    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645   -0.6336    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5395   -0.6336    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6020   -1.3480    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.0145   -2.0625    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.6020   -2.7770    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7770   -2.7770    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.9520   -2.7770    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8395   -2.0625    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.2520   -1.3480    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.8395   -0.6336    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0145   -0.6336    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0770   -1.3480    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4895   -2.0625    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.0770   -2.7770    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2520   -2.7770    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3145   -2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1058   -0.5235    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7766   -0.9108    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4270   -2.7770    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1895   -0.6336    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.6336    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1270    0.0809    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1105   -0.6336    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  1  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  1  6  1  0  0  0  0
  4  7  1  0  0  0  0
  4  8  1  0  0  0  0
  2  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
  1 12  1  0  0  0  0
 10 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  1  0  0  0
 15 16  1  0  0  0  0
  9 16  1  0  0  0  0
 16 17  1  6  0  0  0
  9 17  1  6  0  0  0
 14 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  1  0  0  0
 20 21  1  0  0  0  0
 13 21  1  0  0  0  0
 19 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 18 25  1  0  0  0  0
 23 26  1  1  0  0  0
 22 27  1  0  0  0  0
 22 28  1  0  0  0  0
 18 29  1  1  0  0  0
 13 30  1  1  0  0  0
  1 31  1  1  0  0  0
 31 32  2  0  0  0  0
 31 33  1  0  0  0  0
M  END


  Mrv1652304292205562D          

 33 38  0  0  1  0            999 V2000
    1.1270   -1.3480    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.5395   -2.0625    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.1270   -2.7770    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3020   -2.7770    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1105   -2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3020   -1.3480    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2732   -3.6015    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3977   -3.2142    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645   -2.0625    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.7770   -1.3480    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645   -0.6336    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5395   -0.6336    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6020   -1.3480    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.0145   -2.0625    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.6020   -2.7770    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7770   -2.7770    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.9520   -2.7770    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8395   -2.0625    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.2520   -1.3480    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.8395   -0.6336    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0145   -0.6336    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0770   -1.3480    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4895   -2.0625    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.0770   -2.7770    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2520   -2.7770    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3145   -2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1058   -0.5235    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7766   -0.9108    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4270   -2.7770    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1895   -0.6336    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.6336    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1270    0.0809    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1105   -0.6336    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  1  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  1  6  1  0  0  0  0
  4  7  1  0  0  0  0
  4  8  1  0  0  0  0
  2  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
  1 12  1  0  0  0  0
 10 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  1  0  0  0
 15 16  1  0  0  0  0
  9 16  1  0  0  0  0
 16 17  1  6  0  0  0
  9 17  1  6  0  0  0
 14 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  1  0  0  0
 20 21  1  0  0  0  0
 13 21  1  0  0  0  0
 19 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 18 25  1  0  0  0  0
 23 26  1  1  0  0  0
 22 27  1  0  0  0  0
 22 28  1  0  0  0  0
 18 29  1  1  0  0  0
 13 30  1  1  0  0  0
  1 31  1  1  0  0  0
 31 32  2  0  0  0  0
 31 33  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0082861

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1(C)CC[C@@]2(CC=C3[C@]4(C[C@H]4C[C@@H]4[C@@]5(C)CC[C@H](O)C(C)(C)[C@@H]5CC[C@@]34C)[C@H]2C1)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C30H46O3/c1-25(2)13-14-29(24(32)33)12-8-20-28(6)10-7-19-26(3,4)23(31)9-11-27(19,5)21(28)15-18-16-30(18,20)22(29)17-25/h8,18-19,21-23,31H,7,9-17H2,1-6H3,(H,32,33)/t18-,19+,21-,22+,23+,27+,28+,29-,30-/m1/s1

> <INCHI_KEY>
ZVTPITMTNGHPJR-CSWHDHOSSA-N

> <FORMULA>
C30H46O3

> <MOLECULAR_WEIGHT>
454.695

> <EXACT_MASS>
454.344695341

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
79

> <JCHEM_AVERAGE_POLARIZABILITY>
54.32440840600023

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1S,3R,5R,6R,9S,11R,14R,18S,23R)-9-hydroxy-6,10,10,14,21,21-hexamethylhexacyclo[13.8.0.0^{1,3}.0^{5,14}.0^{6,11}.0^{18,23}]tricos-15-ene-18-carboxylic acid

> <ALOGPS_LOGP>
5.78

> <JCHEM_LOGP>
5.973557961999999

> <ALOGPS_LOGS>
-5.60

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
19.489433241353257

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.663566884617373

> <JCHEM_PKA_STRONGEST_BASIC>
-0.8351232777467

> <JCHEM_POLAR_SURFACE_AREA>
57.53

> <JCHEM_REFRACTIVITY>
131.76989999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.15e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1S,3R,5R,6R,9S,11R,14R,18S,23R)-9-hydroxy-6,10,10,14,21,21-hexamethylhexacyclo[13.8.0.0^{1,3}.0^{5,14}.0^{6,11}.0^{18,23}]tricos-15-ene-18-carboxylic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 29-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   29-APR-22         0                                  
HETATM    1  C   UNK     0       2.104  -2.516   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.874  -3.850   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.104  -5.184   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.564  -5.184   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -0.206  -3.850   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.564  -2.516   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.510  -6.723   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -0.742  -6.000   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.414  -3.850   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.184  -2.516   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.414  -1.183   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.874  -1.183   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       6.724  -2.516   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       7.494  -3.850   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       6.724  -5.184   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       5.184  -5.184   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       3.644  -5.184   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       9.034  -3.850   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       9.804  -2.516   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       9.034  -1.183   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       7.494  -1.183   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      11.344  -2.516   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      12.114  -3.850   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      11.344  -5.184   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       9.804  -5.184   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0      13.654  -3.850   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0      11.397  -0.977   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      12.650  -1.700   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       8.264  -5.184   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       5.954  -1.183   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       1.334  -1.183   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0       2.104   0.151   0.000  0.00  0.00           O+0
HETATM   33  O   UNK     0      -0.206  -1.183   0.000  0.00  0.00           O+0
CONECT    1    2    6   12   31                                             
CONECT    2    1    3    9                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5    7    8                                             
CONECT    5    4    6                                                       
CONECT    6    5    1                                                       
CONECT    7    4                                                            
CONECT    8    4                                                            
CONECT    9    2   10   16   17                                             
CONECT   10    9   11   13                                                  
CONECT   11   10   12                                                       
CONECT   12   11    1                                                       
CONECT   13   10   14   21   30                                             
CONECT   14   13   15   18                                                  
CONECT   15   14   16                                                       
CONECT   16   15    9   17                                                  
CONECT   17   16    9                                                       
CONECT   18   14   19   25   29                                             
CONECT   19   18   20   22                                                  
CONECT   20   19   21                                                       
CONECT   21   20   13                                                       
CONECT   22   19   23   27   28                                             
CONECT   23   22   24   26                                                  
CONECT   24   23   25                                                       
CONECT   25   24   18                                                       
CONECT   26   23                                                            
CONECT   27   22                                                            
CONECT   28   22                                                            
CONECT   29   18                                                            
CONECT   30   13                                                            
CONECT   31    1   32   33                                                  
CONECT   32   31                                                            
CONECT   33   31                                                            
MASTER        0    0    0    0    0    0    0    0   33    0   76    0
END

View in JSmol

Synonyms

Value	Source
(1S,3R,5R,6R,9S,11R,14R,18S,23R)-9-Hydroxy-6,10,10,14,21,21-hexamethylhexacyclo[13.8.0.0,.0,.0,.0,]tricos-15-ene-18-carboxylate	Generator

Chemical Formula

C₃₀H₄₆O₃

Average Mass

454.6950 Da

Monoisotopic Mass

454.34470 Da

IUPAC Name

(1S,3R,5R,6R,9S,11R,14R,18S,23R)-9-hydroxy-6,10,10,14,21,21-hexamethylhexacyclo[13.8.0.0^{1,3}.0^{5,14}.0^{6,11}.0^{18,23}]tricos-15-ene-18-carboxylic acid

Traditional Name

(1S,3R,5R,6R,9S,11R,14R,18S,23R)-9-hydroxy-6,10,10,14,21,21-hexamethylhexacyclo[13.8.0.0^{1,3}.0^{5,14}.0^{6,11}.0^{18,23}]tricos-15-ene-18-carboxylic acid

CAS Registry Number

Not Available

SMILES

CC1(C)CC[C@@]2(CC=C3[C@]4(C[C@H]4C[C@@H]4[C@@]5(C)CC[C@H](O)C(C)(C)[C@@H]5CC[C@@]34C)[C@H]2C1)C(O)=O

InChI Identifier

InChI=1S/C30H46O3/c1-25(2)13-14-29(24(32)33)12-8-20-28(6)10-7-19-26(3,4)23(31)9-11-27(19,5)21(28)15-18-16-30(18,20)22(29)17-25/h8,18-19,21-23,31H,7,9-17H2,1-6H3,(H,32,33)/t18-,19+,21-,22+,23+,27+,28+,29-,30-/m1/s1

InChI Key

ZVTPITMTNGHPJR-CSWHDHOSSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Paeonia suffruticosa	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as cyclic alcohols and derivatives. These are organic compounds containing an aliphatic ring substituted with at least one hydroxyl group.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Alcohols and polyols

Direct Parent

Cyclic alcohols and derivatives

Alternative Parents

Substituents

Cyclic alcohol
Secondary alcohol
Monocarboxylic acid or derivatives
Carboxylic acid
Carboxylic acid derivative
Organic oxide
Hydrocarbon derivative
Carbonyl group
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	5.78	ALOGPS
logP	5.97	ChemAxon
logS	-5.6	ALOGPS
pKa (Strongest Acidic)	4.66	ChemAxon
pKa (Strongest Basic)	-0.84	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	57.53 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	131.77 m³·mol⁻¹	ChemAxon
Polarizability	54.32 Å³	ChemAxon
Number of Rings	6	ChemAxon
Bioavailability	Yes	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

163100868

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for (+)-Mudanpinoic acid A (NP0082861)

MOL for NP0082861 ((+)-Mudanpinoic acid A)

3D MOL for NP0082861 ((+)-Mudanpinoic acid A)

3D SDF for NP0082861 ((+)-Mudanpinoic acid A)

3D-SDF for NP0082861 ((+)-Mudanpinoic acid A)

PDB for NP0082861 ((+)-Mudanpinoic acid A)

3D PDB for NP0082861 ((+)-Mudanpinoic acid A)

SMILES for NP0082861 ((+)-Mudanpinoic acid A)

INCHI for NP0082861 ((+)-Mudanpinoic acid A)

Structure for NP0082861 ((+)-Mudanpinoic acid A)

3D Structure for NP0082861 ((+)-Mudanpinoic acid A)