NP-MRD: Showing NP-Card for (1'r,3r,6'r,7's,9'r)-2-formyl-7'-hydroxy-3-methyl-10'-methylidene-2',11'-dioxo-3'-oxaspiro[cyclohexane-1,5'-tricyclo[7.2.1.0¹,⁶]dodecan]-3-ylmethyl acetate (NP0241338)

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Record Information

Version

2.0

Created at

2022-09-07 01:23:39 UTC

Updated at

2022-09-07 01:23:39 UTC

NP-MRD ID

NP0241338

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1'r,3r,6'r,7's,9'r)-2-formyl-7'-hydroxy-3-methyl-10'-methylidene-2',11'-dioxo-3'-oxaspiro[cyclohexane-1,5'-tricyclo[7.2.1.0¹,⁶]dodecan]-3-ylmethyl acetate

Description

Trichorabdal B belongs to the class of organic compounds known as diterpene lactones. These are diterpenoids containing a lactone moiety. (1'r,3r,6'r,7's,9'r)-2-formyl-7'-hydroxy-3-methyl-10'-methylidene-2',11'-dioxo-3'-oxaspiro[cyclohexane-1,5'-tricyclo[7.2.1.0¹,⁶]dodecan]-3-ylmethyl acetate is found in Isodon effusus, Isodon enanderianus, Isodon trichocarpus and Isodon xerophilus. (1'r,3r,6'r,7's,9'r)-2-formyl-7'-hydroxy-3-methyl-10'-methylidene-2',11'-dioxo-3'-oxaspiro[cyclohexane-1,5'-tricyclo[7.2.1.0¹,⁶]dodecan]-3-ylmethyl acetate was first documented in 2012 (PMID: 22978208). Based on a literature review very few articles have been published on Trichorabdal B.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309072203232D          

 29 32  0  0  1  0            999 V2000
   -1.5934    0.0346    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7732   -0.0536    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3405   -0.8079    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6942   -1.5532    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5433   -0.6618    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.2321   -0.0191    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1943    0.5868    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.5250    1.0670    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2946    0.6824    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.9953    1.1179    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2988   -0.1972    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.0329   -0.6099    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0256    0.2151    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7364    0.6339    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4545    0.2277    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4618   -0.5973    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.2729   -0.4469    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7508   -1.3700    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5645   -1.5061    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8535   -2.2788    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6672   -2.4149    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3288   -2.9155    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7510   -1.0161    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7582   -1.8411    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0474   -2.2598    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0565   -1.4412    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3537   -1.8845    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6211   -1.5020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0639   -1.9617    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  3  5  1  0  0  0  0
  5  6  1  6  0  0  0
  7  6  1  6  0  0  0
  2  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  6  0  0  0
  9 11  1  0  0  0  0
 11  5  1  6  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  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  6  0  0  0
 16 18  1  1  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 20 22  2  0  0  0  0
 16 23  1  0  0  0  0
 12 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  2  0  0  0  0
 12 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
  5 28  1  0  0  0  0
 28 29  2  0  0  0  0
M  END

     RDKit          3D

 57 60  0  0  0  0  0  0  0  0999 V2000
   -5.6644   -0.7744   -1.0235 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6303   -0.2725   -0.3890 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8151    0.8432   -0.8474 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9962    1.5443   -1.8626 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6954    0.9822    0.1636 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.4900    0.6044    1.4130 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0746   -0.7232    0.9112 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.0000   -1.7320    0.7466 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5877   -1.1454    0.7583 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.1307   -0.9429    2.0405 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5908    0.0362   -0.1318 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.2217    0.7334   -0.2360 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.1562    1.3986    1.0216 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3100    0.8553    1.7830 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0160   -0.2923    1.1274 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1846   -0.0694   -0.3713 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.8950    1.1904   -0.6021 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8965   -1.2825   -0.8746 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1163   -1.5875   -0.3638 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3515   -1.0598   -0.4370 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5353   -1.6468    0.2949 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5212   -0.0374   -1.1443 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7736   -0.1117   -0.9277 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.7945    0.0985   -2.4211 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1025   -0.5651   -3.1759 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5505    1.8590   -1.2464 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2068    2.8571   -0.4869 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3502    2.4030    0.2000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0720    3.1916    0.8380 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2357   -1.6050   -0.6373 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9880   -0.3684   -1.9718 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9150    0.5238    2.3173 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2960    1.3413    1.5095 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8391   -1.1160    1.5990 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0775   -2.6042    1.4421 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1208   -2.1867   -0.2805 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9649   -1.9969    0.3491 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5224   -1.6393    2.6188 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7533   -0.3486   -1.1840 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7375    1.3304    1.7163 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2893    2.5098    0.9260 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0550    0.5294    2.8147 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1008    1.6511    1.9400 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4769   -1.2498    1.2556 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0331   -0.4354    1.5436 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3356    1.3010   -1.6056 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2458    2.1009   -0.3754 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7046    1.3079    0.1435 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2187   -2.2049   -0.7326 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9513   -1.2637   -2.0147 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2221   -2.2106    1.1827 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2288   -0.8545    0.6162 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0617   -2.2681   -0.4427 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4720   -1.1795   -0.8134 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4223    0.8455   -2.8903 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2636    1.5053   -2.0150 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3191    2.2307   -1.7677 H   0  0  0  0  0  0  0  0  0  0  0  0
 21 20  1  0
 20 22  2  0
 20 19  1  0
 19 18  1  0
 16 18  1  6
 16 17  1  0
 16 15  1  0
 15 14  1  0
 14 13  1  0
 12 13  1  1
 12 26  1  0
 26 27  1  0
 27 28  1  0
 28 29  2  0
  5 28  1  1
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
  9 11  1  0
  7  2  1  0
  2  1  2  3
  2  3  1  0
  3  4  2  0
 12 23  1  0
 23 24  1  0
 24 25  2  0
 23 16  1  0
 11 12  1  0
 11  5  1  0
  3  5  1  0
 21 51  1  0
 21 52  1  0
 21 53  1  0
 18 49  1  0
 18 50  1  0
 17 46  1  0
 17 47  1  0
 17 48  1  0
 15 44  1  0
 15 45  1  0
 14 42  1  0
 14 43  1  0
 13 40  1  0
 13 41  1  0
 26 56  1  0
 26 57  1  0
  6 32  1  0
  6 33  1  0
  7 34  1  1
  8 35  1  0
  8 36  1  0
  9 37  1  6
 10 38  1  0
 11 39  1  6
  1 30  1  0
  1 31  1  0
 23 54  1  6
 24 55  1  0
M  END


  Mrv1652309072203232D          

 29 32  0  0  1  0            999 V2000
   -1.5934    0.0346    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7732   -0.0536    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3405   -0.8079    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6942   -1.5532    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5433   -0.6618    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.2321   -0.0191    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1943    0.5868    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.5250    1.0670    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2946    0.6824    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.9953    1.1179    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2988   -0.1972    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.0329   -0.6099    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0256    0.2151    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7364    0.6339    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4545    0.2277    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4618   -0.5973    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.2729   -0.4469    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7508   -1.3700    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5645   -1.5061    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8535   -2.2788    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6672   -2.4149    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3288   -2.9155    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7510   -1.0161    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7582   -1.8411    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0474   -2.2598    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0565   -1.4412    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3537   -1.8845    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6211   -1.5020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0639   -1.9617    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  3  5  1  0  0  0  0
  5  6  1  6  0  0  0
  7  6  1  6  0  0  0
  2  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  6  0  0  0
  9 11  1  0  0  0  0
 11  5  1  6  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  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  6  0  0  0
 16 18  1  1  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 20 22  2  0  0  0  0
 16 23  1  0  0  0  0
 12 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  2  0  0  0  0
 12 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
  5 28  1  0  0  0  0
 28 29  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0241338

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(=O)OC[C@]1(C)CCCC2(COC(=O)[C@]34C[C@H](C[C@H](O)[C@H]23)C(=C)C4=O)C1C=O

> <INCHI_IDENTIFIER>
InChI=1S/C22H28O7/c1-12-14-7-15(25)17-21(11-29-19(27)22(17,8-14)18(12)26)6-4-5-20(3,16(21)9-23)10-28-13(2)24/h9,14-17,25H,1,4-8,10-11H2,2-3H3/t14-,15-,16?,17+,20-,21?,22+/m0/s1

> <INCHI_KEY>
BUJZGALXYNSLEB-LNMOHGOKSA-N

> <FORMULA>
C22H28O7

> <MOLECULAR_WEIGHT>
404.459

> <EXACT_MASS>
404.183503242

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
57

> <JCHEM_AVERAGE_POLARIZABILITY>
41.56851561434732

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
[(1'R,3R,6'R,7'S,9'R)-2-formyl-7'-hydroxy-3-methyl-10'-methylidene-2',11'-dioxo-3'-oxaspiro[cyclohexane-1,5'-tricyclo[7.2.1.0^{1,6}]dodecane]-3-yl]methyl acetate

> <JCHEM_LOGP>
1.128606259000002

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
16.484644159485512

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.827295647822009

> <JCHEM_PKA_STRONGEST_BASIC>
-2.8637088496390923

> <JCHEM_POLAR_SURFACE_AREA>
106.97

> <JCHEM_REFRACTIVITY>
101.47789999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(1'R,3R,6'R,7'S,9'R)-2-formyl-7'-hydroxy-3-methyl-10'-methylidene-2',11'-dioxo-3'-oxaspiro[cyclohexane-1,5'-tricyclo[7.2.1.0^{1,6}]dodecane]-3-ylmethyl acetate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 07-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   07-SEP-22         0                                  
HETATM    1  C   UNK     0      -2.974   0.065   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.443  -0.100   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -0.636  -1.508   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0      -1.296  -2.899   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       1.014  -1.235   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.433  -0.036   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -0.363   1.095   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.980   1.992   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.417   1.274   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       3.725   2.087   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       2.424  -0.368   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       3.795  -1.138   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       3.781   0.401   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       5.108   1.183   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       6.448   0.425   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       6.462  -1.115   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       7.976  -0.834   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       7.001  -2.557   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       8.520  -2.811   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       9.060  -4.254   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      10.579  -4.508   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       8.080  -5.442   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       5.135  -1.897   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       5.149  -3.437   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       3.822  -4.218   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0       3.839  -2.690   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0       2.527  -3.518   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0       1.159  -2.804   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0      -0.119  -3.662   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    7                                                  
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6   11   28                                             
CONECT    6    5    7                                                       
CONECT    7    6    2    8                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9    5   12                                                  
CONECT   12   11   13   23   26                                             
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17   18   23                                             
CONECT   17   16                                                            
CONECT   18   16   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20                                                            
CONECT   23   16   12   24                                                  
CONECT   24   23   25                                                       
CONECT   25   24                                                            
CONECT   26   12   27                                                       
CONECT   27   26   28                                                       
CONECT   28   27    5   29                                                  
CONECT   29   28                                                            
MASTER        0    0    0    0    0    0    0    0   29    0   64    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₂H₂₈O₇

Average Mass

404.4590 Da

Monoisotopic Mass

404.18350 Da

IUPAC Name

[(1'R,3R,6'R,7'S,9'R)-2-formyl-7'-hydroxy-3-methyl-10'-methylidene-2',11'-dioxo-3'-oxaspiro[cyclohexane-1,5'-tricyclo[7.2.1.0^{1,6}]dodecane]-3-yl]methyl acetate

Traditional Name

(1'R,3R,6'R,7'S,9'R)-2-formyl-7'-hydroxy-3-methyl-10'-methylidene-2',11'-dioxo-3'-oxaspiro[cyclohexane-1,5'-tricyclo[7.2.1.0^{1,6}]dodecane]-3-ylmethyl acetate

CAS Registry Number

Not Available

SMILES

CC(=O)OC[C@]1(C)CCCC2(COC(=O)[C@]34C[C@H](C[C@H](O)[C@H]23)C(=C)C4=O)C1C=O

InChI Identifier

InChI=1S/C22H28O7/c1-12-14-7-15(25)17-21(11-29-19(27)22(17,8-14)18(12)26)6-4-5-20(3,16(21)9-23)10-28-13(2)24/h9,14-17,25H,1,4-8,10-11H2,2-3H3/t14-,15-,16?,17+,20-,21?,22+/m0/s1

InChI Key

BUJZGALXYNSLEB-LNMOHGOKSA-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
Isodon effusus	LOTUS Database	35616633
Isodon enanderianus	LOTUS Database	35616633
Isodon trichocarpus	LOTUS Database	35616633
Isodon xerophilus	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as diterpene lactones. These are diterpenoids containing a lactone moiety.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Terpene lactones

Direct Parent

Diterpene lactones

Alternative Parents

Substituents

Kaurane diterpenoid
Diterpenoid
Diterpene lactone
Delta_valerolactone
Delta valerolactone
Oxane
Dicarboxylic acid or derivatives
Cyclic alcohol
Secondary alcohol
Lactone
Ketone
Carboxylic acid ester
Oxacycle
Organoheterocyclic compound
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aldehyde
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	1.13	ChemAxon
pKa (Strongest Acidic)	14.83	ChemAxon
pKa (Strongest Basic)	-2.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	106.97 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	101.48 m³·mol⁻¹	ChemAxon
Polarizability	41.57 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

C00040550

Chemspider ID

109418

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

122739

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Ohsaki A, Ozawa M, Komiyama K, Kishida A, Isobe T: The cytotoxic activity of diterpenoids from Isodon species. Nat Prod Commun. 2012 Aug;7(8):977-8. [PubMed:22978208 ]
LOTUS database [Link]

Showing NP-Card for (1'r,3r,6'r,7's,9'r)-2-formyl-7'-hydroxy-3-methyl-10'-methylidene-2',11'-dioxo-3'-oxaspiro[cyclohexane-1,5'-tricyclo[7.2.1.0¹,⁶]dodecan]-3-ylmethyl acetate (NP0241338)

MOL for NP0241338 ((1'r,3r,6'r,7's,9'r)-2-formyl-7'-hydroxy-3-methyl-10'-methylidene-2',11'-dioxo-3'-oxaspiro[cyclohexane-1,5'-tricyclo[7.2.1.0¹,⁶]dodecan]-3-ylmethyl acetate)

3D MOL for NP0241338 ((1'r,3r,6'r,7's,9'r)-2-formyl-7'-hydroxy-3-methyl-10'-methylidene-2',11'-dioxo-3'-oxaspiro[cyclohexane-1,5'-tricyclo[7.2.1.0¹,⁶]dodecan]-3-ylmethyl acetate)

3D SDF for NP0241338 ((1'r,3r,6'r,7's,9'r)-2-formyl-7'-hydroxy-3-methyl-10'-methylidene-2',11'-dioxo-3'-oxaspiro[cyclohexane-1,5'-tricyclo[7.2.1.0¹,⁶]dodecan]-3-ylmethyl acetate)

3D-SDF for NP0241338 ((1'r,3r,6'r,7's,9'r)-2-formyl-7'-hydroxy-3-methyl-10'-methylidene-2',11'-dioxo-3'-oxaspiro[cyclohexane-1,5'-tricyclo[7.2.1.0¹,⁶]dodecan]-3-ylmethyl acetate)

PDB for NP0241338 ((1'r,3r,6'r,7's,9'r)-2-formyl-7'-hydroxy-3-methyl-10'-methylidene-2',11'-dioxo-3'-oxaspiro[cyclohexane-1,5'-tricyclo[7.2.1.0¹,⁶]dodecan]-3-ylmethyl acetate)

3D PDB for NP0241338 ((1'r,3r,6'r,7's,9'r)-2-formyl-7'-hydroxy-3-methyl-10'-methylidene-2',11'-dioxo-3'-oxaspiro[cyclohexane-1,5'-tricyclo[7.2.1.0¹,⁶]dodecan]-3-ylmethyl acetate)

SMILES for NP0241338 ((1'r,3r,6'r,7's,9'r)-2-formyl-7'-hydroxy-3-methyl-10'-methylidene-2',11'-dioxo-3'-oxaspiro[cyclohexane-1,5'-tricyclo[7.2.1.0¹,⁶]dodecan]-3-ylmethyl acetate)

INCHI for NP0241338 ((1'r,3r,6'r,7's,9'r)-2-formyl-7'-hydroxy-3-methyl-10'-methylidene-2',11'-dioxo-3'-oxaspiro[cyclohexane-1,5'-tricyclo[7.2.1.0¹,⁶]dodecan]-3-ylmethyl acetate)

Structure for NP0241338 ((1'r,3r,6'r,7's,9'r)-2-formyl-7'-hydroxy-3-methyl-10'-methylidene-2',11'-dioxo-3'-oxaspiro[cyclohexane-1,5'-tricyclo[7.2.1.0¹,⁶]dodecan]-3-ylmethyl acetate)

3D Structure for NP0241338 ((1'r,3r,6'r,7's,9'r)-2-formyl-7'-hydroxy-3-methyl-10'-methylidene-2',11'-dioxo-3'-oxaspiro[cyclohexane-1,5'-tricyclo[7.2.1.0¹,⁶]dodecan]-3-ylmethyl acetate)