NP-MRD: Showing NP-Card for (-)-Cyclocoulterone (NP0079868)

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Record Information

Version

2.0

Created at

2022-04-29 00:56:39 UTC

Updated at

2022-04-29 00:56:39 UTC

NP-MRD ID

NP0079868

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(-)-Cyclocoulterone

Description

Cyclocoulterone belongs to the class of organic compounds known as diterpenoids. These are terpene compounds formed by four isoprene units. (-)-Cyclocoulterone is found in Dracocephalum komarovi. (-)-Cyclocoulterone was first documented in 2003 (PMID: 12542361). Based on a literature review a small amount of articles have been published on cyclocoulterone (PMID: 27896867) (PMID: 29289245).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304292202562D          

 26 29  0  0  1  0            999 V2000
    4.3006    2.0848    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7433    2.7809    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3618    3.5124    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5376    3.5478    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.0948    2.8516    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.4763    2.1201    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2745    2.7637    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6944    3.3503    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7912    4.1696    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1301    4.6631    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3721    4.3373    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2753    3.5180    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9364    3.0245    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6713    2.2432    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1536    2.2539    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3984    3.0418    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2890    4.8308    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0469    4.5050    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1921    5.6501    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2269    5.4824    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4921    4.6047    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4042    5.4250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2693    4.3280    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7054    2.1244    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0795    3.9192    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4259    4.3349    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
  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
  5  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  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
 12 13  2  0  0  0  0
  8 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 12 16  1  0  0  0  0
 11 17  1  0  0  0  0
 17 18  1  0  0  0  0
 17 19  1  0  0  0  0
 10 20  1  0  0  0  0
  9 21  1  0  0  0  0
 21 22  2  0  0  0  0
 21 23  1  0  0  0  0
  4 23  1  1  0  0  0
  5 24  1  1  0  0  0
  3 25  1  0  0  0  0
  3 26  1  0  0  0  0
M  END

     RDKit          3D

 54 57  0  0  0  0  0  0  0  0999 V2000
    5.2709   -1.3372   -1.3062 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5479   -1.1392    0.0675 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.4960   -0.0233    0.6798 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2586   -0.4784   -0.1329 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1095   -1.2991   -0.0868 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2510   -2.6554    0.0371 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8579   -0.7378   -0.1697 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7309    0.6088   -0.2896 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8238    1.4602   -0.3396 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1065    0.8809   -0.2600 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9964    1.9604   -0.3293 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2709    3.1044    0.1939 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0100    2.8497   -0.4533 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4978    1.3984   -0.3634 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5625    0.7873    0.5101 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.9522    0.3650    1.6921 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5402    1.8896    0.8882 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5276    1.3299    1.8612 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0979    0.0164    1.4639 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7270   -0.4227    0.0892 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.4989    0.3630   -0.9334 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1978   -1.8813   -0.0354 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2465   -0.3452   -0.1862 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.6238   -1.6991    0.1227 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2086   -1.7375   -0.1950 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2092   -2.8798   -0.5900 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8905   -0.5774   -1.9871 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0367   -2.4031   -1.6423 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3528   -1.3005   -1.1373 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5980   -1.9824    0.6996 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7799    0.6666   -0.1398 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4486   -0.5955    0.9209 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1246    0.3693    1.5917 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1293   -3.1415    0.0896 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1787    2.9886    1.3036 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7102    4.0577   -0.1249 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3023    2.4566   -0.0536 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8645    1.3906   -1.4112 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5110   -0.3172    2.1558 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9466    2.6842    1.3754 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0112    2.3725    0.0098 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0041    1.2024    2.8489 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3337    2.0852    2.1188 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2223    0.1086    1.4925 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8678   -0.7988    2.2005 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8233    0.7335   -1.7204 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0917    1.1610   -0.4612 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2504   -0.2687   -1.4949 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1221   -2.2334   -1.0788 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7315   -2.5369    0.6983 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3112   -1.8473    0.1714 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1321   -0.1820   -1.2748 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8349   -2.0491    1.1433 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1471   -2.4208   -0.5787 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  2  0
  5  6  1  0
  5  7  1  0
  7  8  2  0
  8 14  1  0
 14 15  1  0
 15 16  1  1
 15 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  6
 20 22  1  0
 20 23  1  0
 23 24  1  0
 24 25  1  0
 25 26  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 10  4  1  0
 25  7  1  0
 13  9  1  0
 23 15  1  0
  1 27  1  0
  1 28  1  0
  1 29  1  0
  2 30  1  1
  3 31  1  0
  3 32  1  0
  3 33  1  0
  6 34  1  0
 14 37  1  0
 14 38  1  0
 16 39  1  0
 17 40  1  0
 17 41  1  0
 18 42  1  0
 18 43  1  0
 19 44  1  0
 19 45  1  0
 21 46  1  0
 21 47  1  0
 21 48  1  0
 22 49  1  0
 22 50  1  0
 22 51  1  0
 23 52  1  6
 24 53  1  0
 24 54  1  0
 12 35  1  0
 12 36  1  0
M  END


  Mrv1652304292202562D          

 26 29  0  0  1  0            999 V2000
    4.3006    2.0848    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7433    2.7809    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3618    3.5124    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5376    3.5478    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.0948    2.8516    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.4763    2.1201    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2745    2.7637    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6944    3.3503    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7912    4.1696    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1301    4.6631    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3721    4.3373    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2753    3.5180    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9364    3.0245    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6713    2.2432    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1536    2.2539    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3984    3.0418    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2890    4.8308    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0469    4.5050    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1921    5.6501    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2269    5.4824    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4921    4.6047    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4042    5.4250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2693    4.3280    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7054    2.1244    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0795    3.9192    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4259    4.3349    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
  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
  5  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  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
 12 13  2  0  0  0  0
  8 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 12 16  1  0  0  0  0
 11 17  1  0  0  0  0
 17 18  1  0  0  0  0
 17 19  1  0  0  0  0
 10 20  1  0  0  0  0
  9 21  1  0  0  0  0
 21 22  2  0  0  0  0
 21 23  1  0  0  0  0
  4 23  1  1  0  0  0
  5 24  1  1  0  0  0
  3 25  1  0  0  0  0
  3 26  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0079868

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)C1=C(O)C2=C(C[C@@]3(O)CCCC(C)(C)[C@@H]3CC2=O)C2=C1OCO2

> <INCHI_IDENTIFIER>
InChI=1S/C21H28O5/c1-11(2)15-17(23)16-12(18-19(15)26-10-25-18)9-21(24)7-5-6-20(3,4)14(21)8-13(16)22/h11,14,23-24H,5-10H2,1-4H3/t14-,21-/m0/s1

> <INCHI_KEY>
DTBDZSSMCMSRSI-QKKBWIMNSA-N

> <FORMULA>
C21H28O5

> <MOLECULAR_WEIGHT>
360.45

> <EXACT_MASS>
360.193674002

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
54

> <JCHEM_AVERAGE_POLARIZABILITY>
39.5369013140256

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(3S,8S)-3,12-dihydroxy-7,7-dimethyl-13-(propan-2-yl)-15,17-dioxatetracyclo[9.7.0.0^{3,8}.0^{14,18}]octadeca-1(11),12,14(18)-trien-10-one

> <ALOGPS_LOGP>
3.27

> <JCHEM_LOGP>
4.289632971333334

> <ALOGPS_LOGS>
-3.77

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.285630965569151

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.902196430726702

> <JCHEM_PKA_STRONGEST_BASIC>
-3.111565795270007

> <JCHEM_POLAR_SURFACE_AREA>
75.99

> <JCHEM_REFRACTIVITY>
97.9921

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.07e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(3S,8S)-3,12-dihydroxy-13-isopropyl-7,7-dimethyl-15,17-dioxatetracyclo[9.7.0.0^{3,8}.0^{14,18}]octadeca-1(11),12,14(18)-trien-10-one

> <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       8.028   3.892   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       8.854   5.191   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       8.142   6.557   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       6.603   6.623   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       5.777   5.323   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       6.489   3.958   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.246   5.159   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       3.163   6.254   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       3.344   7.783   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.110   8.704   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.695   8.096   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       0.514   6.567   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.748   5.646   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       1.253   4.187   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0      -0.287   4.207   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      -0.744   5.678   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0      -0.539   9.018   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -1.954   8.409   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -0.359  10.547   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       2.290  10.234   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       4.652   8.595   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       4.488  10.127   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       6.103   8.079   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       5.050   3.965   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       9.482   7.316   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       8.262   8.092   0.000  0.00  0.00           C+0
CONECT    1    2    6                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4   25   26                                             
CONECT    4    3    5   23                                                  
CONECT    5    4    6    7   24                                             
CONECT    6    5    1                                                       
CONECT    7    5    8                                                       
CONECT    8    7    9   13                                                  
CONECT    9    8   10   21                                                  
CONECT   10    9   11   20                                                  
CONECT   11   10   12   17                                                  
CONECT   12   11   13   16                                                  
CONECT   13   12    8   14                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   12                                                       
CONECT   17   11   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17                                                            
CONECT   20   10                                                            
CONECT   21    9   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21    4                                                       
CONECT   24    5                                                            
CONECT   25    3                                                            
CONECT   26    3                                                            
MASTER        0    0    0    0    0    0    0    0   26    0   58    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₁H₂₈O₅

Average Mass

360.4500 Da

Monoisotopic Mass

360.19367 Da

IUPAC Name

(3S,8S)-3,12-dihydroxy-7,7-dimethyl-13-(propan-2-yl)-15,17-dioxatetracyclo[9.7.0.0^{3,8}.0^{14,18}]octadeca-1(11),12,14(18)-trien-10-one

Traditional Name

(3S,8S)-3,12-dihydroxy-13-isopropyl-7,7-dimethyl-15,17-dioxatetracyclo[9.7.0.0^{3,8}.0^{14,18}]octadeca-1(11),12,14(18)-trien-10-one

CAS Registry Number

Not Available

SMILES

CC(C)C1=C(O)C2=C(C[C@@]3(O)CCCC(C)(C)[C@@H]3CC2=O)C2=C1OCO2

InChI Identifier

InChI=1S/C21H28O5/c1-11(2)15-17(23)16-12(18-19(15)26-10-25-18)9-21(24)7-5-6-20(3,4)14(21)8-13(16)22/h11,14,23-24H,5-10H2,1-4H3/t14-,21-/m0/s1

InChI Key

DTBDZSSMCMSRSI-QKKBWIMNSA-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, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, 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
Dracocephalum komarovi	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as diterpenoids. These are terpene compounds formed by four isoprene units.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Diterpenoids

Direct Parent

Diterpenoids

Alternative Parents

Substituents

Abeoabietane diterpenoid
Diterpenoid
Benzodioxole
Aryl ketone
Aryl alkyl ketone
Benzenoid
Cyclic alcohol
Tertiary alcohol
Vinylogous acid
Ketone
Acetal
Oxacycle
Organoheterocyclic compound
Alcohol
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic 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	3.27	ALOGPS
logP	4.29	ChemAxon
logS	-3.8	ALOGPS
pKa (Strongest Acidic)	9.9	ChemAxon
pKa (Strongest Basic)	-3.1	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	75.99 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	97.99 m³·mol⁻¹	ChemAxon
Polarizability	39.54 Å³	ChemAxon
Number of Rings	4	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

C00044673

Chemspider ID

8265461

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

10089924

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Thommen C, Neuburger M, Gademann K: Collective Syntheses of Icetexane Natural Products Based on Biogenetic Hypotheses. Chemistry. 2017 Jan 1;23(1):120-127. doi: 10.1002/chem.201603932. Epub 2016 Nov 29. [PubMed:27896867 ]
Liffert R, Gademann K: Mapping Out Biogenetic Hypotheses by Chemical Synthesis. Chimia (Aarau). 2017 Dec 1;71(12):841-844. doi: 10.2533/chimia.2017.841. [PubMed:29289245 ]
Uchiyama N, Kiuchi F, Ito M, Honda G, Takeda Y, Khodzhimatov OK, Ashurmetov OA: New icetexane and 20 norabietane diterpenes with trypanocidal activity from Dracocephalum komarovi. J Nat Prod. 2003 Jan;66(1):128-31. doi: 10.1021/np020308z. [PubMed:12542361 ]

Showing NP-Card for (-)-Cyclocoulterone (NP0079868)

MOL for NP0079868 ((-)-Cyclocoulterone)

3D MOL for NP0079868 ((-)-Cyclocoulterone)

3D SDF for NP0079868 ((-)-Cyclocoulterone)

3D-SDF for NP0079868 ((-)-Cyclocoulterone)

PDB for NP0079868 ((-)-Cyclocoulterone)

3D PDB for NP0079868 ((-)-Cyclocoulterone)

SMILES for NP0079868 ((-)-Cyclocoulterone)

INCHI for NP0079868 ((-)-Cyclocoulterone)

Structure for NP0079868 ((-)-Cyclocoulterone)

3D Structure for NP0079868 ((-)-Cyclocoulterone)