NP-MRD: Showing NP-Card for (1s,2s,3s,5s,8s,9s,11r,13r,16s,18r)-3,13,18-trihydroxy-16-methoxy-12,12-dimethyl-6-methylidene-17-oxapentacyclo[7.6.2.1⁵,⁸.0¹,¹¹.0²,⁸]octadecan-7-one (NP0320027)

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Record Information

Version

2.0

Created at

2022-09-11 21:22:30 UTC

Updated at

2022-09-11 21:22:31 UTC

NP-MRD ID

NP0320027

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1s,2s,3s,5s,8s,9s,11r,13r,16s,18r)-3,13,18-trihydroxy-16-methoxy-12,12-dimethyl-6-methylidene-17-oxapentacyclo[7.6.2.1⁵,⁸.0¹,¹¹.0²,⁸]octadecan-7-one

Description

ISOLUSHININ F 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. (1s,2s,3s,5s,8s,9s,11r,13r,16s,18r)-3,13,18-trihydroxy-16-methoxy-12,12-dimethyl-6-methylidene-17-oxapentacyclo[7.6.2.1⁵,⁸.0¹,¹¹.0²,⁸]octadecan-7-one is found in Isodon rubescens. It was first documented in 2022 (PMID: 36127115). Based on a literature review a significant number of articles have been published on ISOLUSHININ F (PMID: 36127064) (PMID: 36126836) (PMID: 36126944) (PMID: 36126765) (PMID: 36126640) (PMID: 36126636).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309112223222D          

 27 31  0  0  1  0            999 V2000
    8.0426    0.5621    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1606    0.7090    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5098    0.1607    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5642   -0.7372    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7125    0.5225    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.3718   -0.3283    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.4614   -0.5384    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9937    0.2493    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.2149   -0.0961    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2155   -1.0034    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4737   -0.5881    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6733    0.5475    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.8071    0.4515    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8368    1.3701    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6087    1.6961    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2614    1.1436    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.9121    0.7386    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.7676    0.9450    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.6283    0.6576    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7130    0.0236    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1851    1.3189    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.5685    2.0914    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.2770    2.9949    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4063    2.1789    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9876    1.5520    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.2731    1.1479    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.9952    1.9528    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
  5  3  1  1  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  8  7  1  6  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  9 11  1  0  0  0  0
  9 12  1  0  0  0  0
 12 13  1  6  0  0  0
 12 14  1  0  0  0  0
 14 15  1  0  0  0  0
 16 15  1  6  0  0  0
  8 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  1  0  0  0
 18 19  1  0  0  0  0
 17 20  1  0  0  0  0
  6 20  1  1  0  0  0
 16 21  1  0  0  0  0
 21  5  1  6  0  0  0
 21 22  1  0  0  0  0
 22 23  1  1  0  0  0
 22 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25  2  1  1  0  0  0
 25 26  1  0  0  0  0
  5 26  1  0  0  0  0
 26 27  1  6  0  0  0
M  END

     RDKit          2D

 57 61  0  0  0  0  0  0  0  0999 V2000
   -5.2841   -0.8638    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9138   -0.2537    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6147   -1.0037    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4579   -2.4955    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7500   -1.2990    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7500   -1.2990    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4095   -0.5130    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7395   -1.4772    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7500    1.2990    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8991    2.2632    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0000    2.5981    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5000    2.5981    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7500    1.2990    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3828    0.5621    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6491    0.9642    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0586    0.4512    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2954   -0.6125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7500    1.2990    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5000    2.5981    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7605    4.0753    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0000    2.5981    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7500    1.2990    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7395   -1.4772    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4976    0.0179    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4409   -2.3556    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5000   -2.5981    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4895   -2.7762    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8820   -2.2832    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9134   -1.4419    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8191   -1.0261    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0906    0.8235    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0722   -1.9746    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4791   -2.9544    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1740   -1.9158    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3130   -1.9409    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0982    0.6416    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3086    1.7502    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7395    4.0753    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4095    3.1111    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2565    3.4369    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7605    4.0753    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3816   -1.2136    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3951   -0.2299    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8975    1.6947    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7212   -1.0104    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000    2.5981    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2565    3.4369    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0970    4.7563    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4095    3.1111    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9215    4.0960    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2500    1.2990    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2435   -0.8389    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8886   -2.4414    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
 19 18  1  0
 18 17  1  0
 17 20  1  0
 20  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
  9 11  1  0
  9 12  1  0
 12 13  1  0
 12 14  1  0
 14 15  1  0
 16 15  1  1
 16 21  1  0
 21 22  1  0
 22 23  1  0
 22 24  1  0
 24 25  1  0
 25 26  1  0
 26 27  1  0
 26  5  1  0
  5  3  1  6
  3  4  2  0
  3  2  1  0
  2  1  2  3
 16 17  1  0
  5 21  1  0
  5  6  1  0
 16  8  1  0
  2 25  1  0
 19 47  1  0
 19 48  1  0
 19 49  1  0
 17 46  1  6
  6 30  1  6
  7 31  1  0
  7 32  1  0
  8 33  1  6
 10 34  1  0
 10 35  1  0
 10 36  1  0
 11 37  1  0
 11 38  1  0
 11 39  1  0
 12 40  1  6
 13 41  1  0
 14 42  1  0
 14 43  1  0
 15 44  1  0
 15 45  1  0
 21 50  1  6
 22 51  1  1
 23 52  1  0
 24 53  1  0
 24 54  1  0
 25 55  1  1
 26 56  1  1
 27 57  1  0
  1 28  1  0
  1 29  1  0
M  END


  Mrv1652309112223222D          

 27 31  0  0  1  0            999 V2000
    8.0426    0.5621    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1606    0.7090    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5098    0.1607    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5642   -0.7372    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7125    0.5225    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.3718   -0.3283    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.4614   -0.5384    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9937    0.2493    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.2149   -0.0961    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2155   -1.0034    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4737   -0.5881    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6733    0.5475    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.8071    0.4515    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8368    1.3701    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6087    1.6961    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2614    1.1436    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.9121    0.7386    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.7676    0.9450    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.6283    0.6576    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7130    0.0236    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1851    1.3189    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.5685    2.0914    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.2770    2.9949    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4063    2.1789    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9876    1.5520    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.2731    1.1479    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.9952    1.9528    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
  5  3  1  1  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  8  7  1  6  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  9 11  1  0  0  0  0
  9 12  1  0  0  0  0
 12 13  1  6  0  0  0
 12 14  1  0  0  0  0
 14 15  1  0  0  0  0
 16 15  1  6  0  0  0
  8 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  1  0  0  0
 18 19  1  0  0  0  0
 17 20  1  0  0  0  0
  6 20  1  1  0  0  0
 16 21  1  0  0  0  0
 21  5  1  6  0  0  0
 21 22  1  0  0  0  0
 22 23  1  1  0  0  0
 22 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25  2  1  1  0  0  0
 25 26  1  0  0  0  0
  5 26  1  0  0  0  0
 26 27  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0320027

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CO[C@H]1O[C@H]2C[C@@H]3C(C)(C)[C@H](O)CC[C@]13[C@@H]1[C@@H](O)C[C@@H]3[C@@H](O)[C@]21C(=O)C3=C

> <INCHI_IDENTIFIER>
InChI=1S/C21H30O6/c1-9-10-7-11(22)15-20-6-5-13(23)19(2,3)12(20)8-14(27-18(20)26-4)21(15,16(9)24)17(10)25/h10-15,17-18,22-23,25H,1,5-8H2,2-4H3/t10-,11-,12+,13+,14-,15-,17+,18-,20-,21+/m0/s1

> <INCHI_KEY>
PFNVKSDNOBXQRP-OOPPFOIBSA-N

> <FORMULA>
C21H30O6

> <MOLECULAR_WEIGHT>
378.465

> <EXACT_MASS>
378.204238686

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
57

> <JCHEM_AVERAGE_POLARIZABILITY>
30.07147341697307

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1S,2S,3S,5S,8S,9S,11R,13R,16S,18R)-3,13,18-trihydroxy-16-methoxy-12,12-dimethyl-6-methylidene-17-oxapentacyclo[7.6.2.1^{5,8}.0^{1,11}.0^{2,8}]octadecan-7-one

> <JCHEM_LOGP>
0.6973798776666672

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.940387684967064

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.04564989179405

> <JCHEM_PKA_STRONGEST_BASIC>
-0.8349588219990646

> <JCHEM_POLAR_SURFACE_AREA>
96.22000000000001

> <JCHEM_REFRACTIVITY>
96.49910000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(1S,2S,3S,5S,8S,9S,11R,13R,16S,18R)-3,13,18-trihydroxy-16-methoxy-12,12-dimethyl-6-methylidene-17-oxapentacyclo[7.6.2.1^{5,8}.0^{1,11}.0^{2,8}]octadecan-7-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 11-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   11-SEP-22         0                                  
HETATM    1  C   UNK     0      15.013   1.049   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      13.366   1.324   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      12.152   0.300   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0      12.253  -1.376   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0      10.663   0.975   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      10.027  -0.613   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       8.328  -1.005   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       7.455   0.465   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       6.001  -0.179   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       6.002  -1.873   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.618  -1.098   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.990   1.022   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       3.373   0.843   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       5.295   2.557   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       6.736   3.166   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       7.955   2.135   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       9.169   1.379   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      10.766   1.764   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0      12.373   1.228   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       8.798   0.044   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       9.679   2.462   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      10.394   3.904   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       9.850   5.591   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0      11.958   4.067   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      13.043   2.897   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      11.710   2.143   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0      11.191   3.645   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   25                                                  
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6   21   26                                             
CONECT    6    5    7   20                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   16                                                  
CONECT    9    8   10   11   12                                             
CONECT   10    9                                                            
CONECT   11    9                                                            
CONECT   12    9   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15    8   17   21                                             
CONECT   17   16   18   20                                                  
CONECT   18   17   19                                                       
CONECT   19   18                                                            
CONECT   20   17    6                                                       
CONECT   21   16    5   22                                                  
CONECT   22   21   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22   25                                                       
CONECT   25   24    2   26                                                  
CONECT   26   25    5   27                                                  
CONECT   27   26                                                            
MASTER        0    0    0    0    0    0    0    0   27    0   62    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₁H₃₀O₆

Average Mass

378.4650 Da

Monoisotopic Mass

378.20424 Da

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

CO[C@H]1O[C@H]2C[C@@H]3C(C)(C)[C@H](O)CC[C@]13[C@@H]1[C@@H](O)C[C@@H]3[C@@H](O)[C@]21C(=O)C3=C

InChI Identifier

InChI=1S/C21H30O6/c1-9-10-7-11(22)15-20-6-5-13(23)19(2,3)12(20)8-14(27-18(20)26-4)21(15,16(9)24)17(10)25/h10-15,17-18,22-23,25H,1,5-8H2,2-4H3/t10-,11-,12+,13+,14-,15-,17+,18-,20-,21+/m0/s1

InChI Key

PFNVKSDNOBXQRP-OOPPFOIBSA-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 rubescens	LOTUS Database	35616633

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
Cyclic alcohol
Ketone
Secondary alcohol
Acetal
Polyol
Oxacycle
Organoheterocyclic compound
Organooxygen compound
Organic oxide
Organic oxygen compound
Hydrocarbon derivative
Alcohol
Carbonyl group
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

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

25035756

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

46906439

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Gao X, Peng Q, Yuan K, Li Y, Shi M, Miao J, Liu X: Monitoring and characterization of prochloraz resistance in Fusarium fujikuroi in China. Pestic Biochem Physiol. 2022 Oct;187:105189. doi: 10.1016/j.pestbp.2022.105189. Epub 2022 Aug 1. [PubMed:36127064 ]
Lu J, Fang X, Liang H, Guo Z, Zou H: Lysine acetylation plays a role in the allograft-induced stress response of the pearl oyster (Pinctada fucata martensii). Fish Shellfish Immunol. 2022 Nov;130:223-232. doi: 10.1016/j.fsi.2022.09.018. Epub 2022 Sep 17. [PubMed:36126836 ]
Rohwer E, Velasco Garrido M, Herold R, Preisser AM, Terschuren C, Harth V, Mache S: Police officers' work-life balance, job satisfaction and quality of life: longitudinal effects after changing the shift schedule. BMJ Open. 2022 Sep 20;12(9):e063302. doi: 10.1136/bmjopen-2022-063302. [PubMed:36127115 ]
Sit CHP, Huang WYJ, Wong SHS, Wong MCS, Sum RKW, Li VMH: Results and SWOT Analysis of the 2022 Hong Kong Report Card on Physical Activity for Children and Adolescents With Special Educational Needs. Adapt Phys Activ Q. 2022 Jan 1:1-9. doi: 10.1123/apaq.2022-0066. [PubMed:36126944 ]
Gong L, Chen C, Liu X, Wu X, Zhu L, Luo J, Kong L: Hainanolide inhibits the progression of colon cancer via inducing the cell cycle arrest, cell apoptosis and activation of the MAPK signaling pathway. Toxicol Appl Pharmacol. 2022 Nov 1;454:116249. doi: 10.1016/j.taap.2022.116249. Epub 2022 Sep 17. [PubMed:36126765 ]
Ozdel Ozturk B, Yavuz Z, Aydin O, Mungan D, Sin BA, Demirel YS, Bavbek S: Effectiveness of Low-Dose Mepolizumab in the Treatment of Eosinophilic Granulomatosis with Polyangiitis (EGPA): A Real-Life Experience. Int Arch Allergy Immunol. 2022;183(12):1281-1290. doi: 10.1159/000526410. Epub 2022 Sep 20. [PubMed:36126640 ]
Kleijkers LMP, Van Der Spil J, Janssen LCE, Dieleman JP, Andriessen P, van Kaam AH, Onland W, Niemarkt HJ: Short-Term Outcome after Repeated Less Invasive Surfactant Administration: A Retrospective Cohort Study. Neonatology. 2022;119(6):719-726. doi: 10.1159/000526493. Epub 2022 Sep 20. [PubMed:36126636 ]
Giebelhaus RT, Sorochan Armstrong MD, de la Mata AP, Harynuk JJ: Untargeted region of interest selection for gas chromatography - mass spectrometry data using a pseudo F-ratio moving window. J Chromatogr A. 2022 Oct 25;1682:463499. doi: 10.1016/j.chroma.2022.463499. Epub 2022 Sep 13. [PubMed:36126562 ]
Rixon L, Hastings RP, Kovshoff H, Bailey T: Short Report: Outcomes for siblings associated with sub-groups of autistic children with intellectual disability identified by latent profile analysis. Res Dev Disabil. 2022 Nov;130:104337. doi: 10.1016/j.ridd.2022.104337. Epub 2022 Sep 17. [PubMed:36126532 ]
Zhang H, Kim MS, Huang J, Yan H, Yang T, Song L, Yu W, Shim WB: Transcriptome analysis of maize pathogen Fusarium verticillioides revealed FvLcp1, a secreted protein with type-D fungal LysM and chitin-binding domains, that plays important roles in pathogenesis and mycotoxin production. Microbiol Res. 2022 Dec;265:127195. doi: 10.1016/j.micres.2022.127195. Epub 2022 Sep 14. [PubMed:36126492 ]
Rangel-Buitrago N, Rodriguez RDB, Moreno JB, Ochoa FL, Neal W: Are sediment textural parameters an "influencer" of microplastics presence in beach environments? Mar Pollut Bull. 2022 Nov;184:114125. doi: 10.1016/j.marpolbul.2022.114125. Epub 2022 Sep 18. [PubMed:36126486 ]
Huang G, Lu X, Qiu Y, Bi L, Ye P, Yang M, Shen Y, Jin H, Han J: Hetero-aryl bromide precursor fluorine-18 radiosynthesis and preclinical evaluation of a novel positron emission tomography (PET) tracer [(18)F]GSK1482160. Bioorg Med Chem. 2022 Nov 1;73:116996. doi: 10.1016/j.bmc.2022.116996. Epub 2022 Sep 15. [PubMed:36126443 ]
Cheng J, Sun J, Yao K, Xu M, Zhou X: Nondestructive detection and visualization of protein oxidation degree of frozen-thawed pork using fluorescence hyperspectral imaging. Meat Sci. 2022 Sep 8;194:108975. doi: 10.1016/j.meatsci.2022.108975. [PubMed:36126392 ]
Rani VJ, Kanakati AK, Mahapatra S: Multi-state and Multi-mode Vibronic Coupling Effects in the Photoionization Spectroscopy of Acetaldehyde. J Phys Chem A. 2022 Sep 29;126(38):6581-6593. doi: 10.1021/acs.jpca.2c03073. Epub 2022 Sep 20. [PubMed:36126257 ]
Pisirici P, Cil ET, Coskunsu DK, Sayli U, Subasi F: Extracorporeal Shockwave Therapy Versus Graston Instrument-Assisted Soft-Tissue Mobilization in Chronic Plantar Heel Pain: A Randomized Controlled Trial. J Am Podiatr Med Assoc. 2022 Nov-Dec;112(6):21-036. doi: 10.7547/21-036. [PubMed:36125974 ]
Bamajboor A, Dudley J: The Influence of Ferrule on the Marginal Gap and Fracture Resistance of Zirconia Endocrowns. Int J Prosthodont. 2022 Jul-Aug;35(4):494-501. doi: 10.11607/ijp.8060. [PubMed:36125874 ]
Sato TP, Arata A, de Miranda LM, Bottino MA, de Melo RM, Zhang Y, Souza ROA: Effect of Porcelain-to-Zirconia Ratio and Bonding Strategy on the Biaxial Flexural Strength and Weibull Characteristics of a Stress-Free Bilayer CAD/CAM Ceramic System. Int J Prosthodont. 2022 Jul-Aug;35(4):469-479. doi: 10.11607/ijp.7551. [PubMed:36125871 ]
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Usman UA, de Moraes ACA, da Silva TGP, Batista AMV, Soares PC, de Araujo CASC, de Carvalho FFR, da Silva Junior VA: Kidney changes in lambs fed cactus pear varieties resistant to Dactylopius opuntiae as the only roughage. Trop Anim Health Prod. 2022 Sep 20;54(5):311. doi: 10.1007/s11250-022-03328-y. [PubMed:36125577 ]
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LOTUS database [Link]

Showing NP-Card for (1s,2s,3s,5s,8s,9s,11r,13r,16s,18r)-3,13,18-trihydroxy-16-methoxy-12,12-dimethyl-6-methylidene-17-oxapentacyclo[7.6.2.1⁵,⁸.0¹,¹¹.0²,⁸]octadecan-7-one (NP0320027)

MOL for NP0320027 ((1s,2s,3s,5s,8s,9s,11r,13r,16s,18r)-3,13,18-trihydroxy-16-methoxy-12,12-dimethyl-6-methylidene-17-oxapentacyclo[7.6.2.1⁵,⁸.0¹,¹¹.0²,⁸]octadecan-7-one)

3D MOL for NP0320027 ((1s,2s,3s,5s,8s,9s,11r,13r,16s,18r)-3,13,18-trihydroxy-16-methoxy-12,12-dimethyl-6-methylidene-17-oxapentacyclo[7.6.2.1⁵,⁸.0¹,¹¹.0²,⁸]octadecan-7-one)

3D SDF for NP0320027 ((1s,2s,3s,5s,8s,9s,11r,13r,16s,18r)-3,13,18-trihydroxy-16-methoxy-12,12-dimethyl-6-methylidene-17-oxapentacyclo[7.6.2.1⁵,⁸.0¹,¹¹.0²,⁸]octadecan-7-one)

3D-SDF for NP0320027 ((1s,2s,3s,5s,8s,9s,11r,13r,16s,18r)-3,13,18-trihydroxy-16-methoxy-12,12-dimethyl-6-methylidene-17-oxapentacyclo[7.6.2.1⁵,⁸.0¹,¹¹.0²,⁸]octadecan-7-one)

PDB for NP0320027 ((1s,2s,3s,5s,8s,9s,11r,13r,16s,18r)-3,13,18-trihydroxy-16-methoxy-12,12-dimethyl-6-methylidene-17-oxapentacyclo[7.6.2.1⁵,⁸.0¹,¹¹.0²,⁸]octadecan-7-one)

3D PDB for NP0320027 ((1s,2s,3s,5s,8s,9s,11r,13r,16s,18r)-3,13,18-trihydroxy-16-methoxy-12,12-dimethyl-6-methylidene-17-oxapentacyclo[7.6.2.1⁵,⁸.0¹,¹¹.0²,⁸]octadecan-7-one)

SMILES for NP0320027 ((1s,2s,3s,5s,8s,9s,11r,13r,16s,18r)-3,13,18-trihydroxy-16-methoxy-12,12-dimethyl-6-methylidene-17-oxapentacyclo[7.6.2.1⁵,⁸.0¹,¹¹.0²,⁸]octadecan-7-one)

INCHI for NP0320027 ((1s,2s,3s,5s,8s,9s,11r,13r,16s,18r)-3,13,18-trihydroxy-16-methoxy-12,12-dimethyl-6-methylidene-17-oxapentacyclo[7.6.2.1⁵,⁸.0¹,¹¹.0²,⁸]octadecan-7-one)

Structure for NP0320027 ((1s,2s,3s,5s,8s,9s,11r,13r,16s,18r)-3,13,18-trihydroxy-16-methoxy-12,12-dimethyl-6-methylidene-17-oxapentacyclo[7.6.2.1⁵,⁸.0¹,¹¹.0²,⁸]octadecan-7-one)

3D Structure for NP0320027 ((1s,2s,3s,5s,8s,9s,11r,13r,16s,18r)-3,13,18-trihydroxy-16-methoxy-12,12-dimethyl-6-methylidene-17-oxapentacyclo[7.6.2.1⁵,⁸.0¹,¹¹.0²,⁸]octadecan-7-one)