NP-MRD: Showing NP-Card for (1s,4s,8r,9r,12s,13r,14s,16s)-9,14-dihydroxy-7,7-dimethyl-17-methylidene-3,10-dioxapentacyclo[14.2.1.0¹,¹³.0⁴,¹².0⁸,¹²]nonadecane-2,18-dione (NP0274412)

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Record Information

Version

2.0

Created at

2022-09-08 21:47:59 UTC

Updated at

2022-09-08 21:48:00 UTC

NP-MRD ID

NP0274412

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1s,4s,8r,9r,12s,13r,14s,16s)-9,14-dihydroxy-7,7-dimethyl-17-methylidene-3,10-dioxapentacyclo[14.2.1.0¹,¹³.0⁴,¹².0⁸,¹²]nonadecane-2,18-dione

Description

Epinodosin belongs to the class of organic compounds known as diterpene lactones. These are diterpenoids containing a lactone moiety. (1s,4s,8r,9r,12s,13r,14s,16s)-9,14-dihydroxy-7,7-dimethyl-17-methylidene-3,10-dioxapentacyclo[14.2.1.0¹,¹³.0⁴,¹².0⁸,¹²]nonadecane-2,18-dione is found in Isodon henryi, Isodon japonicus, Isodon rubescens and Isodon sculponeatus. (1s,4s,8r,9r,12s,13r,14s,16s)-9,14-dihydroxy-7,7-dimethyl-17-methylidene-3,10-dioxapentacyclo[14.2.1.0¹,¹³.0⁴,¹².0⁸,¹²]nonadecane-2,18-dione was first documented in 2011 (PMID: 19606380). Based on a literature review a small amount of articles have been published on Epinodosin (PMID: 30989952) (PMID: 35903341) (PMID: 21930275) (PMID: 24013676).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309082223482D          

 26 30  0  0  1  0            999 V2000
    5.3176    0.6313    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5139    0.4451    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8570    1.0041    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9473    1.8241    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0563    0.5814    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.5688    0.1187    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1741   -0.3359    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.6992   -1.0413    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8640   -0.9279    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.3763   -1.5933    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4796   -0.1125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.5550   -0.0255    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.9452   -0.7992    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5024   -1.4959    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7236   -1.2436    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0419   -1.7083    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7742   -0.4148    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0023   -0.1091    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1799   -0.9138    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8207   -0.0528    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0680    0.7070    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6061    1.1865    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3712    0.8319    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.9036    1.4754    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7120    1.3383    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2153    1.9920    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  1  0  0  0
  7  6  1  1  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  6  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  1  0  0  0
 17 15  1  6  0  0  0
 12 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 18 20  1  0  0  0  0
 18 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 12 23  1  0  0  0  0
 23 24  1  6  0  0  0
 24 25  1  0  0  0  0
  5 25  1  0  0  0  0
 25 26  2  0  0  0  0
M  END

     RDKit          3D

 52 56  0  0  0  0  0  0  0  0999 V2000
    4.8687   -0.5423    1.5252 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8568   -0.4158    0.7129 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7055   -1.2835    0.6064 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4907   -2.2180    1.4197 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9306   -0.8605   -0.5542 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.9913   -0.1290   -1.4018 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6597    0.6507   -0.2877 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.7581    1.6601    0.3686 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3077    1.4555    0.1618 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.6645    1.7939    1.3823 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8614    0.1496   -0.3783 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.4351   -0.3915    0.1767 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.2503   -0.8189    1.5809 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3487   -0.4268    2.3226 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1340    0.4051    1.5966 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.2867    1.5978    2.2785 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5566    0.5649    0.2044 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.7010    0.3332   -0.7468 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8875    1.1537   -0.2003 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4822    0.8373   -2.1373 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1949   -1.1087   -0.7112 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1233   -2.0755   -0.2435 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8120   -1.5380   -0.7478 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.1852   -2.4833   -0.9188 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4527   -2.0773   -1.2409 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2223   -2.6438   -2.0527 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9776   -1.3434    2.2492 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7018    0.1758    1.5291 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7155   -0.8482   -1.7793 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5296    0.5152   -2.1472 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6234    1.0949   -0.6220 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0960    2.6593    0.0078 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9873    1.6990    1.4770 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9618    2.3127   -0.5057 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7057    2.7635    1.5413 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5665    0.3712   -1.4684 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2112   -1.9389    1.6989 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6197   -0.3955    2.1200 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1593   -0.0696    1.5835 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5920    1.7468    2.9749 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2264    1.6231    0.0239 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4748    1.5983   -1.0605 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6211    0.5351    0.3251 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5337    2.0389    0.3624 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8364    0.0192   -2.8335 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4805    1.1814   -2.3775 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1578    1.7004   -2.4220 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4233   -1.3862   -1.7720 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0574   -1.2496   -0.0382 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1416   -2.2280    0.8557 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2944   -3.0797   -0.7006 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0182   -1.0845   -1.7373 H   0  0  0  0  0  0  0  0  0  0  0  0
 19 18  1  0
 18 20  1  0
 18 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  1  0
 25 26  2  0
  5 25  1  6
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
  9 11  1  0
 11 12  1  0
 12 13  1  1
 13 14  1  0
 14 15  1  0
 15 16  1  0
 15 17  1  0
  7  2  1  0
  2  1  2  3
  2  3  1  0
  3  4  2  0
 17 18  1  0
 12 23  1  0
 17 12  1  0
 11  5  1  0
  3  5  1  0
 19 42  1  0
 19 43  1  0
 19 44  1  0
 20 45  1  0
 20 46  1  0
 20 47  1  0
 21 48  1  0
 21 49  1  0
 22 50  1  0
 22 51  1  0
 23 52  1  6
  6 29  1  0
  6 30  1  0
  7 31  1  6
  8 32  1  0
  8 33  1  0
  9 34  1  6
 10 35  1  0
 11 36  1  6
 13 37  1  0
 13 38  1  0
 15 39  1  6
 16 40  1  0
 17 41  1  1
  1 27  1  0
  1 28  1  0
M  END


  Mrv1652309082223482D          

 26 30  0  0  1  0            999 V2000
    5.3176    0.6313    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5139    0.4451    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8570    1.0041    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9473    1.8241    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0563    0.5814    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.5688    0.1187    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1741   -0.3359    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.6992   -1.0413    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8640   -0.9279    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.3763   -1.5933    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4796   -0.1125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.5550   -0.0255    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.9452   -0.7992    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5024   -1.4959    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7236   -1.2436    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0419   -1.7083    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7742   -0.4148    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0023   -0.1091    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1799   -0.9138    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8207   -0.0528    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0680    0.7070    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6061    1.1865    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3712    0.8319    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.9036    1.4754    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7120    1.3383    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2153    1.9920    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  1  0  0  0
  7  6  1  1  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  6  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  1  0  0  0
 17 15  1  6  0  0  0
 12 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 18 20  1  0  0  0  0
 18 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 12 23  1  0  0  0  0
 23 24  1  6  0  0  0
 24 25  1  0  0  0  0
  5 25  1  0  0  0  0
 25 26  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0274412

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1(C)CC[C@@H]2OC(=O)[C@@]34C[C@@H](C[C@H](O)[C@@H]3[C@]22CO[C@@H](O)[C@H]12)C(=C)C4=O

> <INCHI_IDENTIFIER>
InChI=1S/C20H26O6/c1-9-10-6-11(21)13-19(7-10,15(9)22)17(24)26-12-4-5-18(2,3)14-16(23)25-8-20(12,13)14/h10-14,16,21,23H,1,4-8H2,2-3H3/t10-,11+,12+,13+,14-,16-,19+,20+/m1/s1

> <INCHI_KEY>
WZYJEEIAFBHYJS-HBJCYBSRSA-N

> <FORMULA>
C20H26O6

> <MOLECULAR_WEIGHT>
362.422

> <EXACT_MASS>
362.172938557

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
52

> <JCHEM_AVERAGE_POLARIZABILITY>
37.10149153117851

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1S,4S,8R,9R,12S,13R,14S,16S)-9,14-dihydroxy-7,7-dimethyl-17-methylidene-3,10-dioxapentacyclo[14.2.1.0^{1,13}.0^{4,12}.0^{8,12}]nonadecane-2,18-dione

> <JCHEM_LOGP>
1.2847357846666663

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.848473104012076

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.145317533389088

> <JCHEM_PKA_STRONGEST_BASIC>
-2.8655450251501176

> <JCHEM_POLAR_SURFACE_AREA>
93.06

> <JCHEM_REFRACTIVITY>
90.72799999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(1S,4S,8R,9R,12S,13R,14S,16S)-9,14-dihydroxy-7,7-dimethyl-17-methylidene-3,10-dioxapentacyclo[14.2.1.0^{1,13}.0^{4,12}.0^{8,12}]nonadecane-2,18-dione

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 08-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   08-SEP-22         0                                  
HETATM    1  C   UNK     0       9.926   1.178   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       8.426   0.831   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       7.200   1.874   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       7.368   3.405   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       5.705   1.085   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       6.662   0.222   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       7.792  -0.627   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       6.905  -1.944   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.346  -1.732   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       4.436  -2.974   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       4.629  -0.210   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.903  -0.048   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       3.631  -1.492   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       2.804  -2.792   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       1.351  -2.321   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       0.078  -3.189   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       1.445  -0.774   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       0.004  -0.204   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -0.336  -1.706   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -1.532  -0.099   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -0.127   1.320   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       1.131   2.215   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       2.559   1.553   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       3.553   2.754   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       5.062   2.498   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0       6.002   3.718   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   25                                             
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   17   23                                             
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15   12   18                                                  
CONECT   18   17   19   20   21                                             
CONECT   19   18                                                            
CONECT   20   18                                                            
CONECT   21   18   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   12   24                                                  
CONECT   24   23   25                                                       
CONECT   25   24    5   26                                                  
CONECT   26   25                                                            
MASTER        0    0    0    0    0    0    0    0   26    0   60    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₀H₂₆O₆

Average Mass

362.4220 Da

Monoisotopic Mass

362.17294 Da

IUPAC Name

(1S,4S,8R,9R,12S,13R,14S,16S)-9,14-dihydroxy-7,7-dimethyl-17-methylidene-3,10-dioxapentacyclo[14.2.1.0^{1,13}.0^{4,12}.0^{8,12}]nonadecane-2,18-dione

Traditional Name

(1S,4S,8R,9R,12S,13R,14S,16S)-9,14-dihydroxy-7,7-dimethyl-17-methylidene-3,10-dioxapentacyclo[14.2.1.0^{1,13}.0^{4,12}.0^{8,12}]nonadecane-2,18-dione

CAS Registry Number

Not Available

SMILES

CC1(C)CC[C@@H]2OC(=O)[C@@]34C[C@@H](C[C@H](O)[C@@H]3[C@]22CO[C@@H](O)[C@H]12)C(=C)C4=O

InChI Identifier

InChI=1S/C20H26O6/c1-9-10-6-11(21)13-19(7-10,15(9)22)17(24)26-12-4-5-18(2,3)14-16(23)25-8-20(12,13)14/h10-14,16,21,23H,1,4-8H2,2-3H3/t10-,11+,12+,13+,14-,16-,19+,20+/m1/s1

InChI Key

WZYJEEIAFBHYJS-HBJCYBSRSA-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 henryi	LOTUS Database	35616633
Isodon japonicus	LOTUS Database	35616633
Isodon rubescens	LOTUS Database	35616633
Isodon sculponeatus	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

Diterpene lactone
Diterpenoid
Kaurane diterpenoid
Delta valerolactone
Delta_valerolactone
Oxane
Cyclic alcohol
Tetrahydrofuran
Carboxylic acid ester
Hemiacetal
Ketone
Lactone
Secondary alcohol
Organoheterocyclic compound
Carboxylic acid derivative
Monocarboxylic acid or derivatives
Oxacycle
Carbonyl group
Organic oxide
Organic oxygen compound
Alcohol
Hydrocarbon derivative
Organooxygen 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	1.28	ChemAxon
pKa (Strongest Acidic)	12.15	ChemAxon
pKa (Strongest Basic)	-2.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	93.06 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	90.73 m³·mol⁻¹	ChemAxon
Polarizability	37.1 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

C00031769

Chemspider ID

57257073

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

102004749

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Zhang LX, Liu YL, Wu H, Chen SQ, Dai LP: [Studies on chemical constituents of Isodon henryi]. Zhongguo Zhong Yao Za Zhi. 2019 Jan;44(2):319-323. doi: 10.19540/j.cnki.cjcmm.20181101.009. [PubMed:30989952 ]
Ding L, Zhou Q, Wang L, Wang W, Zhang S, Liu B: Comparison of cytotoxicity and DNA damage potential induced by ent-kaurene diterpenoids from Isodon plant. Nat Prod Res. 2011 Sep;25(15):1402-11. doi: 10.1080/14786410802267734. Epub 2011 Jul 8. [PubMed:19606380 ]
Liu F, Zeng Y, Dai P, Huang K, Zhang K, Tao T, Wang M, Zhu C, Lin C: Comparative Pharmacokinetics of Three Bioactive Diterpenoids of Rabdosia serra Extract in Normal and Con A-Induced Liver Injury Rats Using UPLC-MS/MS. Front Pharmacol. 2022 Jul 12;13:944949. doi: 10.3389/fphar.2022.944949. eCollection 2022. [PubMed:35903341 ]
Du Y, Liu P, Zhu H, Shi X, Zhao C, Wang N, Zhang L: A sensitive analysis method for 7 diterpenoids in rat plasma by liquid chromatography-electrospray ionization mass spectrometry and its application to pharmacokinetic study of Isodon serra extract. J Chromatogr A. 2011 Oct 28;1218(43):7771-80. doi: 10.1016/j.chroma.2011.08.033. Epub 2011 Aug 17. [PubMed:21930275 ]
Wang T, Wu Yf, Wang Xl: Molecular structure and vibrational bands and 13C chemical shift assignments of both enmein-type diterpenoids by DFT study. Spectrochim Acta A Mol Biomol Spectrosc. 2014 Jan 3;117:449-58. doi: 10.1016/j.saa.2013.08.010. Epub 2013 Aug 22. [PubMed:24013676 ]
LOTUS database [Link]

Showing NP-Card for (1s,4s,8r,9r,12s,13r,14s,16s)-9,14-dihydroxy-7,7-dimethyl-17-methylidene-3,10-dioxapentacyclo[14.2.1.0¹,¹³.0⁴,¹².0⁸,¹²]nonadecane-2,18-dione (NP0274412)

MOL for NP0274412 ((1s,4s,8r,9r,12s,13r,14s,16s)-9,14-dihydroxy-7,7-dimethyl-17-methylidene-3,10-dioxapentacyclo[14.2.1.0¹,¹³.0⁴,¹².0⁸,¹²]nonadecane-2,18-dione)

3D MOL for NP0274412 ((1s,4s,8r,9r,12s,13r,14s,16s)-9,14-dihydroxy-7,7-dimethyl-17-methylidene-3,10-dioxapentacyclo[14.2.1.0¹,¹³.0⁴,¹².0⁸,¹²]nonadecane-2,18-dione)

3D SDF for NP0274412 ((1s,4s,8r,9r,12s,13r,14s,16s)-9,14-dihydroxy-7,7-dimethyl-17-methylidene-3,10-dioxapentacyclo[14.2.1.0¹,¹³.0⁴,¹².0⁸,¹²]nonadecane-2,18-dione)

3D-SDF for NP0274412 ((1s,4s,8r,9r,12s,13r,14s,16s)-9,14-dihydroxy-7,7-dimethyl-17-methylidene-3,10-dioxapentacyclo[14.2.1.0¹,¹³.0⁴,¹².0⁸,¹²]nonadecane-2,18-dione)

PDB for NP0274412 ((1s,4s,8r,9r,12s,13r,14s,16s)-9,14-dihydroxy-7,7-dimethyl-17-methylidene-3,10-dioxapentacyclo[14.2.1.0¹,¹³.0⁴,¹².0⁸,¹²]nonadecane-2,18-dione)

3D PDB for NP0274412 ((1s,4s,8r,9r,12s,13r,14s,16s)-9,14-dihydroxy-7,7-dimethyl-17-methylidene-3,10-dioxapentacyclo[14.2.1.0¹,¹³.0⁴,¹².0⁸,¹²]nonadecane-2,18-dione)

SMILES for NP0274412 ((1s,4s,8r,9r,12s,13r,14s,16s)-9,14-dihydroxy-7,7-dimethyl-17-methylidene-3,10-dioxapentacyclo[14.2.1.0¹,¹³.0⁴,¹².0⁸,¹²]nonadecane-2,18-dione)

INCHI for NP0274412 ((1s,4s,8r,9r,12s,13r,14s,16s)-9,14-dihydroxy-7,7-dimethyl-17-methylidene-3,10-dioxapentacyclo[14.2.1.0¹,¹³.0⁴,¹².0⁸,¹²]nonadecane-2,18-dione)

Structure for NP0274412 ((1s,4s,8r,9r,12s,13r,14s,16s)-9,14-dihydroxy-7,7-dimethyl-17-methylidene-3,10-dioxapentacyclo[14.2.1.0¹,¹³.0⁴,¹².0⁸,¹²]nonadecane-2,18-dione)

3D Structure for NP0274412 ((1s,4s,8r,9r,12s,13r,14s,16s)-9,14-dihydroxy-7,7-dimethyl-17-methylidene-3,10-dioxapentacyclo[14.2.1.0¹,¹³.0⁴,¹².0⁸,¹²]nonadecane-2,18-dione)