NP-MRD: Showing NP-Card for Shikokianin (NP0075777)

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Record Information

Version

2.0

Created at

2022-04-28 21:00:43 UTC

Updated at

2022-04-28 21:00:43 UTC

NP-MRD ID

NP0075777

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Shikokianin

Description

(1S,2S,3R,5S,8S,9S,10S,11R,15S)-15-(acetyloxy)-9,10-dihydroxy-12,12-dimethyl-6-methylidene-7-oxo-17-oxapentacyclo[7.6.2.1⁵,⁸.0¹,¹¹.0²,⁸]Octadecan-3-yl acetate belongs to the class of organic compounds known as kaurane diterpenoids. These are diterpene alkaloids with a structure that is based on the kaurane skeleton. Kaurane is a tetracyclic compound that arises by cyclisation of a pimarane precursor followed by rearrangement. It possesses a [3,2,1]-bicyclic ring system with C15-C16 bridge connected to C13, forming the five-membered ring D. Shikokianin is found in Isodon enanderianus, Isodon japonica, Isodon parvifolius and Rabdosia shikokiana. Based on a literature review very few articles have been published on (1S,2S,3R,5S,8S,9S,10S,11R,15S)-15-(acetyloxy)-9,10-dihydroxy-12,12-dimethyl-6-methylidene-7-oxo-17-oxapentacyclo[7.6.2.1⁵,⁸.0¹,¹¹.0²,⁸]Octadecan-3-yl acetate.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652304282223002D          

 32 36  0  0  1  0            999 V2000
    7.3349   -0.7720    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6004    0.0200    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9763    0.5828    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1341    0.4235    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.8274   -0.4538    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.5193   -0.9618    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.3535   -1.7700    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.9705   -2.3176    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8047   -3.1258    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.7533   -2.0571    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9206   -0.6791    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.3622    0.1026    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.7341    0.9050    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.6118    1.1973    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.8774    1.9784    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1845    1.5203    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4550    0.6284    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1273   -0.0775    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5366    0.3968    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4488    1.2171    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8222   -0.0464    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0491    0.2416    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0821   -0.8796    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.5820   -1.5689    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4244   -1.3877    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.8806   -2.0751    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7040   -2.0238    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0712   -1.2850    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1602   -2.7112    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8131   -0.5412    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5371    1.1879    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8120    1.3912    0.0000 C   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
  4  3  1  6  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  1  6  1  0  0  0  0
  6  7  1  6  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  8 10  1  0  0  0  0
  5 11  1  0  0  0  0
 11 12  1  6  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
  4 14  1  0  0  0  0
 14 15  1  1  0  0  0
 13 16  1  6  0  0  0
 13 17  1  0  0  0  0
 17 18  1  0  0  0  0
  5 18  1  1  0  0  0
 12 19  1  0  0  0  0
 19 20  2  0  0  0  0
 19 21  1  0  0  0  0
 21 22  2  0  0  0  0
 21 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 11 25  1  0  0  0  0
 25 26  1  6  0  0  0
 26 27  1  0  0  0  0
 27 28  2  0  0  0  0
 27 29  1  0  0  0  0
 23 30  1  6  0  0  0
 12 30  1  6  0  0  0
  3 31  1  0  0  0  0
  3 32  1  0  0  0  0
M  END


  Mrv1652304282223002D          

 32 36  0  0  1  0            999 V2000
    7.3349   -0.7720    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6004    0.0200    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9763    0.5828    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1341    0.4235    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.8274   -0.4538    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.5193   -0.9618    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.3535   -1.7700    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.9705   -2.3176    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8047   -3.1258    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.7533   -2.0571    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9206   -0.6791    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.3622    0.1026    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.7341    0.9050    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.6118    1.1973    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.8774    1.9784    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1845    1.5203    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4550    0.6284    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1273   -0.0775    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5366    0.3968    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4488    1.2171    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8222   -0.0464    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0491    0.2416    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0821   -0.8796    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.5820   -1.5689    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4244   -1.3877    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.8806   -2.0751    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7040   -2.0238    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0712   -1.2850    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1602   -2.7112    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8131   -0.5412    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5371    1.1879    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8120    1.3912    0.0000 C   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
  4  3  1  6  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  1  6  1  0  0  0  0
  6  7  1  6  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  8 10  1  0  0  0  0
  5 11  1  0  0  0  0
 11 12  1  6  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
  4 14  1  0  0  0  0
 14 15  1  1  0  0  0
 13 16  1  6  0  0  0
 13 17  1  0  0  0  0
 17 18  1  0  0  0  0
  5 18  1  1  0  0  0
 12 19  1  0  0  0  0
 19 20  2  0  0  0  0
 19 21  1  0  0  0  0
 21 22  2  0  0  0  0
 21 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 11 25  1  0  0  0  0
 25 26  1  6  0  0  0
 26 27  1  0  0  0  0
 27 28  2  0  0  0  0
 27 29  1  0  0  0  0
 23 30  1  6  0  0  0
 12 30  1  6  0  0  0
  3 31  1  0  0  0  0
  3 32  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0075777

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(=O)O[C@@H]1C[C@@H]2C[C@]3([C@@H]1[C@]14CO[C@]3(O)[C@@H](O)[C@@H]1C(C)(C)CC[C@@H]4OC(C)=O)C(=O)C2=C

> <INCHI_IDENTIFIER>
InChI=1S/C24H32O8/c1-11-14-8-15(31-12(2)25)17-22-10-30-24(29,23(17,9-14)19(11)27)20(28)18(22)21(4,5)7-6-16(22)32-13(3)26/h14-18,20,28-29H,1,6-10H2,2-5H3/t14-,15-,16+,17+,18-,20+,22-,23+,24-/m1/s1

> <INCHI_KEY>
FKKSXNLVJJDMAR-YBKYMNJRSA-N

> <FORMULA>
C24H32O8

> <MOLECULAR_WEIGHT>
448.512

> <EXACT_MASS>
448.20971799

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
64

> <JCHEM_AVERAGE_POLARIZABILITY>
44.60818648970637

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1S,2S,3R,5S,8S,9S,10S,11R,15S)-15-(acetyloxy)-9,10-dihydroxy-12,12-dimethyl-6-methylidene-7-oxo-17-oxapentacyclo[7.6.2.1^{5,8}.0^{1,11}.0^{2,8}]octadecan-3-yl acetate

> <ALOGPS_LOGP>
1.12

> <JCHEM_LOGP>
1.2669515546666665

> <ALOGPS_LOGS>
-2.90

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.795890554734683

> <JCHEM_PKA_STRONGEST_ACIDIC>
10.588706789247064

> <JCHEM_PKA_STRONGEST_BASIC>
-3.683094170281681

> <JCHEM_POLAR_SURFACE_AREA>
119.36000000000001

> <JCHEM_REFRACTIVITY>
110.3343

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.62e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1S,2S,3R,5S,8S,9S,10S,11R,15S)-15-(acetyloxy)-9,10-dihydroxy-12,12-dimethyl-6-methylidene-7-oxo-17-oxapentacyclo[7.6.2.1^{5,8}.0^{1,11}.0^{2,8}]octadecan-3-yl acetate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 28-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   28-APR-22         0                                  
HETATM    1  C   UNK     0      13.692  -1.441   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      14.187   0.037   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      13.022   1.088   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      11.450   0.790   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      10.878  -0.847   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      12.169  -1.795   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      11.860  -3.304   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0      13.012  -4.326   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0      12.702  -5.835   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0      14.473  -3.840   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       9.185  -1.268   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       8.143   0.192   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       8.837   1.689   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      10.475   2.235   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      10.971   3.693   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0       7.811   2.838   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0      10.183   1.173   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       9.571  -0.145   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       6.602   0.741   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       6.438   2.272   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       5.268  -0.087   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       3.825   0.451   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       5.753  -1.642   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       6.686  -2.929   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       8.259  -2.590   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0       9.110  -3.874   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0      10.647  -3.778   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0      11.333  -2.399   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0      11.499  -5.061   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       7.118  -1.010   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      14.069   2.217   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      12.716   2.597   0.000  0.00  0.00           C+0
CONECT    1    2    6                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4   31   32                                             
CONECT    4    3    5   14                                                  
CONECT    5    4    6   11   18                                             
CONECT    6    5    1    7                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8                                                            
CONECT   11    5   12   25                                                  
CONECT   12   11   13   19   30                                             
CONECT   13   12   14   16   17                                             
CONECT   14   13    4   15                                                  
CONECT   15   14                                                            
CONECT   16   13                                                            
CONECT   17   13   18                                                       
CONECT   18   17    5                                                       
CONECT   19   12   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21   24   30                                                  
CONECT   24   23   25                                                       
CONECT   25   24   11   26                                                  
CONECT   26   25   27                                                       
CONECT   27   26   28   29                                                  
CONECT   28   27                                                            
CONECT   29   27                                                            
CONECT   30   23   12                                                       
CONECT   31    3                                                            
CONECT   32    3                                                            
MASTER        0    0    0    0    0    0    0    0   32    0   72    0
END

View in JSmol

Synonyms

Value	Source
(1S,2S,3R,5S,8S,9S,10S,11R,15S)-15-(Acetyloxy)-9,10-dihydroxy-12,12-dimethyl-6-methylidene-7-oxo-17-oxapentacyclo[7.6.2.1,.0,.0,]octadecan-3-yl acetic acid	Generator

Chemical Formula

C₂₄H₃₂O₈

Average Mass

448.5120 Da

Monoisotopic Mass

448.20972 Da

IUPAC Name

(1S,2S,3R,5S,8S,9S,10S,11R,15S)-15-(acetyloxy)-9,10-dihydroxy-12,12-dimethyl-6-methylidene-7-oxo-17-oxapentacyclo[7.6.2.1^{5,8}.0^{1,11}.0^{2,8}]octadecan-3-yl acetate

Traditional Name

(1S,2S,3R,5S,8S,9S,10S,11R,15S)-15-(acetyloxy)-9,10-dihydroxy-12,12-dimethyl-6-methylidene-7-oxo-17-oxapentacyclo[7.6.2.1^{5,8}.0^{1,11}.0^{2,8}]octadecan-3-yl acetate

CAS Registry Number

Not Available

SMILES

CC(=O)O[C@@H]1C[C@@H]2C[C@]3([C@@H]1[C@]14CO[C@]3(O)[C@@H](O)[C@@H]1C(C)(C)CC[C@@H]4OC(C)=O)C(=O)C2=C

InChI Identifier

InChI=1S/C24H32O8/c1-11-14-8-15(31-12(2)25)17-22-10-30-24(29,23(17,9-14)19(11)27)20(28)18(22)21(4,5)7-6-16(22)32-13(3)26/h14-18,20,28-29H,1,6-10H2,2-5H3/t14-,15-,16+,17+,18-,20+,22-,23+,24-/m1/s1

InChI Key

FKKSXNLVJJDMAR-YBKYMNJRSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Isodon enanderianus	Plant	KNApSAcK
Isodon japonica	Plant	KNApSAcK
Isodon parvifolius	Plant	KNApSAcK
Rabdosia shikokiana	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as kaurane diterpenoids. These are diterpene alkaloids with a structure that is based on the kaurane skeleton. Kaurane is a tetracyclic compound that arises by cyclisation of a pimarane precursor followed by rearrangement. It possesses a [3,2,1]-bicyclic ring system with C15-C16 bridge connected to C13, forming the five-membered ring D.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Diterpenoids

Direct Parent

Kaurane diterpenoids

Alternative Parents

Substituents

Kaurane diterpenoid
Oxane
Dicarboxylic acid or derivatives
Cyclic alcohol
Secondary alcohol
Ketone
Hemiacetal
Carboxylic acid ester
Oxacycle
Organoheterocyclic compound
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Alcohol
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	1.12	ALOGPS
logP	1.27	ChemAxon
logS	-2.9	ALOGPS
pKa (Strongest Acidic)	10.59	ChemAxon
pKa (Strongest Basic)	-3.7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	119.36 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	110.33 m³·mol⁻¹	ChemAxon
Polarizability	44.61 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	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

163069459

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Shikokianin (NP0075777)

MOL for NP0075777 (Shikokianin)

3D MOL for NP0075777 (Shikokianin)

3D SDF for NP0075777 (Shikokianin)

3D-SDF for NP0075777 (Shikokianin)

PDB for NP0075777 (Shikokianin)

3D PDB for NP0075777 (Shikokianin)

SMILES for NP0075777 (Shikokianin)

INCHI for NP0075777 (Shikokianin)

Structure for NP0075777 (Shikokianin)

3D Structure for NP0075777 (Shikokianin)