NP-MRD: Showing NP-Card for Oridonin (NP0073109)

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Record Information

Version

2.0

Created at

2022-04-28 18:22:18 UTC

Updated at

2022-04-28 18:22:18 UTC

NP-MRD ID

NP0073109

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Oridonin

Description

Oridonin, also known as isodonol or lasidonin, 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. Oridonin is found in Isodon excisoides, Isodon japonica, Isodon japonicus, Isodon japonicus Hara., Isodon lasiocarpus, Isodon longitubus, Isodon macrocalyx, Isodon phyllostachys, Isodon rosthornii, Rabdosia rubescens , Isodon rubescens var.rubescens, Isodon rugosus, Isodon serra, Isodon ternifolius, Isodon trichocarpa, Isodon trichocarpus and Rabdosia nervosa. Oridonin was first documented in 2022 (PMID: 35484726). Based on a literature review a small amount of articles have been published on oridonin (PMID: 35469348) (PMID: 35405616) (PMID: 35398392) (PMID: 35360548).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304282220222D          

 26 30  0  0  1  0            999 V2000
    6.5241    1.0395    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.5577    0.8847    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.0909    0.0938    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.2211   -0.2292    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.6836    0.5492    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.8525    0.3410    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2106    0.8777    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4794    1.6696    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3018    1.8681    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.0378    1.4039    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.9538    1.6185    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.3828    2.3704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1963    2.5868    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6883    1.8876    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.0596    1.3430    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2825    1.6201    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2167    0.4365    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6637   -0.2569    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7183    0.9929    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3471    0.3258    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4357    2.6822    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0574   -0.4581    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3199   -0.2890    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9730   -1.0160    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6202   -0.5390    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.0980    0.4468    0.0000 O   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
  5  4  1  6  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  5 10  1  0  0  0  0
 10 11  1  0  0  0  0
  2 11  1  0  0  0  0
 11 12  1  6  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
  1 14  1  0  0  0  0
 14 15  1  1  0  0  0
 15 16  2  0  0  0  0
 15 17  1  0  0  0  0
  2 17  1  1  0  0  0
 17 18  2  0  0  0  0
 10 19  1  6  0  0  0
 19 20  1  0  0  0  0
  3 20  1  0  0  0  0
  9 21  1  6  0  0  0
  6 22  1  0  0  0  0
  6 23  1  0  0  0  0
  4 24  1  1  0  0  0
  3 25  1  6  0  0  0
  1 26  1  1  0  0  0
M  END

     RDKit          3D

 54 58  0  0  0  0  0  0  0  0999 V2000
    4.6064    1.2905   -1.3693 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5814    0.8388   -0.6698 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2502    1.3988   -0.5154 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8479    2.4457   -1.0602 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5235    0.5092    0.3743 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.8561   -0.5830   -0.4135 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.6375   -1.8427   -0.3781 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0742   -1.5315   -0.6904 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6495   -0.4257    0.1351 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.6413   -0.0788    1.2403 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.1522    0.9501    2.0139 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5780   -0.7533    0.0996 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.4687   -0.9238    1.6025 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1425    0.1410    2.2113 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5341    1.1306    1.2801 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.1355    2.1344    2.0062 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7255    1.6157    0.6316 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.5636    2.8097   -0.0711 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2962    0.5162   -0.2695 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.7684    0.4427   -0.2594 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.4182    1.3120    0.8293 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3070    1.0334   -1.5729 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3554   -0.9215   -0.0927 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5906   -2.0242   -0.7097 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1213   -1.9773   -0.5494 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.6310   -3.0893    0.1646 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5571    0.7938   -1.4159 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5271    2.2161   -1.9470 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7374   -0.2790   -1.4881 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2823   -2.5337   -1.1945 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6068   -2.4054    0.5551 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2173   -1.3031   -1.7736 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6657   -2.4496   -0.4933 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6488   -0.6121    0.5307 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3217   -0.9563    1.8004 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3506    1.7044    1.3958 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4665   -1.0551    2.0804 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0811   -1.8659    1.7947 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6952    2.9925    1.8771 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4387    1.8514    1.4600 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1699    3.5224    0.2206 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9205    0.7905   -1.3010 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2189    0.9338    1.8332 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5271    1.1618    0.6644 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2409    2.3764    0.6683 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7032    0.7087   -2.4344 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1160    2.1401   -1.4735 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3811    0.8949   -1.6784 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3739   -0.8958   -0.5837 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6031   -1.1136    0.9932 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9079   -2.1112   -1.7905 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9564   -2.9917   -0.2537 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6639   -2.0613   -1.5794 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8117   -3.8708   -0.4341 H   0  0  0  0  0  0  0  0  0  0  0  0
 20 21  1  1
 20 22  1  0
 20 23  1  0
 23 24  1  0
 24 25  1  0
 25 26  1  0
 25 12  1  0
 12 13  1  1
 13 14  1  0
 14 15  1  0
 15 16  1  1
 15 17  1  0
 17 18  1  0
 17 19  1  0
 15  5  1  0
  5 10  1  0
 10 11  1  0
 10  9  1  0
  9  8  1  0
  8  7  1  0
  7  6  1  0
  9  2  1  0
  2  1  2  3
  2  3  1  0
  3  4  2  0
 19 20  1  0
  6  5  1  0
 19 12  1  0
  5  3  1  6
  6 12  1  0
 21 43  1  0
 21 44  1  0
 21 45  1  0
 22 46  1  0
 22 47  1  0
 22 48  1  0
 23 49  1  0
 23 50  1  0
 24 51  1  0
 24 52  1  0
 25 53  1  6
 26 54  1  0
 13 37  1  0
 13 38  1  0
 16 39  1  0
 17 40  1  1
 18 41  1  0
 19 42  1  6
 10 35  1  1
 11 36  1  0
  9 34  1  1
  8 32  1  0
  8 33  1  0
  7 30  1  0
  7 31  1  0
  6 29  1  6
  1 27  1  0
  1 28  1  0
M  END


  Mrv1652304282220222D          

 26 30  0  0  1  0            999 V2000
    6.5241    1.0395    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.5577    0.8847    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.0909    0.0938    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.2211   -0.2292    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.6836    0.5492    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.8525    0.3410    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2106    0.8777    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4794    1.6696    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3018    1.8681    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.0378    1.4039    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.9538    1.6185    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.3828    2.3704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1963    2.5868    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6883    1.8876    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.0596    1.3430    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2825    1.6201    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2167    0.4365    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6637   -0.2569    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7183    0.9929    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3471    0.3258    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4357    2.6822    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0574   -0.4581    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3199   -0.2890    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9730   -1.0160    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6202   -0.5390    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.0980    0.4468    0.0000 O   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
  5  4  1  6  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  5 10  1  0  0  0  0
 10 11  1  0  0  0  0
  2 11  1  0  0  0  0
 11 12  1  6  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
  1 14  1  0  0  0  0
 14 15  1  1  0  0  0
 15 16  2  0  0  0  0
 15 17  1  0  0  0  0
  2 17  1  1  0  0  0
 17 18  2  0  0  0  0
 10 19  1  6  0  0  0
 19 20  1  0  0  0  0
  3 20  1  0  0  0  0
  9 21  1  6  0  0  0
  6 22  1  0  0  0  0
  6 23  1  0  0  0  0
  4 24  1  1  0  0  0
  3 25  1  6  0  0  0
  1 26  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0073109

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1(C)CC[C@H](O)[C@]23CO[C@](O)([C@@H](O)[C@H]12)[C@@]12[C@H](O)[C@@H](CC[C@@H]31)C(=C)C2=O

> <INCHI_IDENTIFIER>
InChI=1S/C20H28O6/c1-9-10-4-5-11-18-8-26-20(25,19(11,14(9)22)15(10)23)16(24)13(18)17(2,3)7-6-12(18)21/h10-13,15-16,21,23-25H,1,4-8H2,2-3H3/t10-,11-,12-,13+,15+,16-,18+,19-,20+/m0/s1

> <INCHI_KEY>
SDHTXBWLVGWJFT-XKCURVIJSA-N

> <FORMULA>
C20H28O6

> <MOLECULAR_WEIGHT>
364.438

> <EXACT_MASS>
364.188588622

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
54

> <JCHEM_AVERAGE_POLARIZABILITY>
37.8914165615397

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1S,2S,5S,8R,9S,10S,11R,15S,18R)-9,10,15,18-tetrahydroxy-12,12-dimethyl-6-methylidene-17-oxapentacyclo[7.6.2.1^{5,8}.0^{1,11}.0^{2,8}]octadecan-7-one

> <ALOGPS_LOGP>
0.24

> <JCHEM_LOGP>
0.5406081940000007

> <ALOGPS_LOGS>
-1.54

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.587018637355524

> <JCHEM_PKA_STRONGEST_ACIDIC>
10.51331086978204

> <JCHEM_PKA_STRONGEST_BASIC>
-2.9705206541019686

> <JCHEM_POLAR_SURFACE_AREA>
107.22000000000001

> <JCHEM_REFRACTIVITY>
91.87729999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.05e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1S,2S,5S,8R,9S,10S,11R,15S,18R)-9,10,15,18-tetrahydroxy-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                                 28-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   28-APR-22         0                                  
HETATM    1  C   UNK     0      12.178   1.940   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      10.374   1.651   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       9.503   0.175   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       7.879  -0.428   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       6.876   1.025   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       5.325   0.637   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.126   1.638   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.628   3.117   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       6.163   3.487   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       7.537   2.621   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       9.247   3.021   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      10.048   4.425   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      11.566   4.829   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      12.485   3.524   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      11.311   2.507   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       9.861   3.024   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      11.605   0.815   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      12.439  -0.480   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       8.807   1.853   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       8.115   0.608   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0       6.413   5.007   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       5.707  -0.855   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       4.331  -0.539   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       7.416  -1.896   0.000  0.00  0.00           O+0
HETATM   25  O   UNK     0      10.491  -1.006   0.000  0.00  0.00           O+0
HETATM   26  O   UNK     0      13.250   0.834   0.000  0.00  0.00           O+0
CONECT    1    2   14   26                                                  
CONECT    2    1    3   11   17                                             
CONECT    3    2    4   20   25                                             
CONECT    4    3    5   24                                                  
CONECT    5    4    6   10                                                  
CONECT    6    5    7   22   23                                             
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   21                                                  
CONECT   10    9    5   11   19                                             
CONECT   11   10    2   12                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13    1   15                                                  
CONECT   15   14   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15    2   18                                                  
CONECT   18   17                                                            
CONECT   19   10   20                                                       
CONECT   20   19    3                                                       
CONECT   21    9                                                            
CONECT   22    6                                                            
CONECT   23    6                                                            
CONECT   24    4                                                            
CONECT   25    3                                                            
CONECT   26    1                                                            
MASTER        0    0    0    0    0    0    0    0   26    0   60    0
END

View in JSmol

Synonyms

Value	Source
(1alpha,6beta,7alpha,14R)-7,20-Epoxy-1,6,7,14-tetrahydroxykaur-16-en-15-one	ChEBI
Isodonol	ChEBI
Oridonine	ChEBI
(1a,6b,7a,14R)-7,20-Epoxy-1,6,7,14-tetrahydroxykaur-16-en-15-one	Generator
(1Α,6β,7α,14R)-7,20-epoxy-1,6,7,14-tetrahydroxykaur-16-en-15-one	Generator
Lasidonin	MeSH
Oridonin, (1alpha,5alpha,6alpha,7beta,8beta,9alpha,10beta,13beta,14S)-isomer	MeSH
Oridonin, (1alpha,6beta,7alpha,11alpha)-isomer	MeSH
Oridonin, (1alpha,6beta,7alpha,11beta)-isomer	MeSH

Chemical Formula

C₂₀H₂₈O₆

Average Mass

364.4380 Da

Monoisotopic Mass

364.18859 Da

IUPAC Name

(1S,2S,5S,8R,9S,10S,11R,15S,18R)-9,10,15,18-tetrahydroxy-12,12-dimethyl-6-methylidene-17-oxapentacyclo[7.6.2.1^{5,8}.0^{1,11}.0^{2,8}]octadecan-7-one

Traditional Name

(1S,2S,5S,8R,9S,10S,11R,15S,18R)-9,10,15,18-tetrahydroxy-12,12-dimethyl-6-methylidene-17-oxapentacyclo[7.6.2.1^{5,8}.0^{1,11}.0^{2,8}]octadecan-7-one

CAS Registry Number

Not Available

SMILES

CC1(C)CC[C@H](O)[C@]23CO[C@](O)([C@@H](O)[C@H]12)[C@@]12[C@H](O)[C@@H](CC[C@@H]31)C(=C)C2=O

InChI Identifier

InChI=1S/C20H28O6/c1-9-10-4-5-11-18-8-26-20(25,19(11,14(9)22)15(10)23)16(24)13(18)17(2,3)7-6-12(18)21/h10-13,15-16,21,23-25H,1,4-8H2,2-3H3/t10-,11-,12-,13+,15+,16-,18+,19-,20+/m0/s1

InChI Key

SDHTXBWLVGWJFT-XKCURVIJSA-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
Isodon excisoides	LOTUS Database	35616633
Isodon japonica	Plant	KNApSAcK
Isodon japonicus	LOTUS Database	35616633
Isodon japonicus Hara.	Plant	KNApSAcK
Isodon lasiocarpus	Plant	KNApSAcK
Isodon longitubus	LOTUS Database	35616633
Isodon macrocalyx	LOTUS Database	35616633
Isodon phyllostachys	LOTUS Database	35616633
Isodon rosthornii	LOTUS Database	35616633
Isodon rubescens	Plant	KNApSAcK
Isodon rubescens var.rubescens	Plant	KNApSAcK
Isodon rugosus	Plant	KNApSAcK
Isodon serra	LOTUS Database	35616633
Isodon ternifolius	LOTUS Database	35616633
Isodon trichocarpa	Plant	KNApSAcK
Isodon trichocarpus	Plant	KNApSAcK
Rabdosia nervosa	Plant	KNApSAcK

Chemical Taxonomy

Description

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

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Diterpenoids

Direct Parent

Kaurane diterpenoids

Alternative Parents

Substituents

Kaurane diterpenoid
Oxane
Cyclic alcohol
Hemiacetal
Ketone
Secondary alcohol
Oxacycle
Polyol
Organoheterocyclic compound
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
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
logP	0.24	ALOGPS
logP	0.54	ChemAxon
logS	-1.5	ALOGPS
pKa (Strongest Acidic)	10.51	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	107.22 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	91.88 m³·mol⁻¹	ChemAxon
Polarizability	37.89 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

C00033270

Chemspider ID

4478909

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

5321010

PDB ID

Not Available

ChEBI ID

138236

Good Scents ID

rw1760051

References

General References

Zhou YF, Yan BC, Yang Q, Long XY, Zhang DQ, Luo RH, Wang HY, Sun HD, Xue XS, Zheng YT, Puno PT: Harnessing Natural Products by a Pharmacophore-Oriented Semisynthesis Approach for the Discovery of Potential Anti-SARS-CoV-2 Agents. Angew Chem Int Ed Engl. 2022 Jul 11;61(28):e202201684. doi: 10.1002/anie.202201684. Epub 2022 May 12. [PubMed:35484726 ]
Gu H, Gwon MG, Kim JH, Leem J, Lee SJ: Oridonin Attenuates Cisplatin-Induced Acute Kidney Injury via Inhibiting Oxidative Stress, Apoptosis, and Inflammation in Mice. Biomed Res Int. 2022 Apr 16;2022:3002962. doi: 10.1155/2022/3002962. eCollection 2022. [PubMed:35469348 ]
Zhu Y, Wu L, Zhao Y, Wang Z, Lu J, Yu Y, Xiao H, Zhang Y: Discovery of oridonin as a novel agonist for BRS-3. Phytomedicine. 2022 Jun;100:154085. doi: 10.1016/j.phymed.2022.154085. Epub 2022 Apr 3. [PubMed:35405616 ]
Yang H, Wang L, Yang M, Hu J, Zhang E, Peng L: Oridonin attenuates LPS-induced early pulmonary fibrosis by regulating impaired autophagy, oxidative stress, inflammation and EMT. Eur J Pharmacol. 2022 May 15;923:174931. doi: 10.1016/j.ejphar.2022.174931. Epub 2022 Apr 8. [PubMed:35398392 ]
Lin S, Dai S, Lin J, Liang X, Wang W, Huang W, Ye B, Hong X: Oridonin Relieves Angiotensin II-Induced Cardiac Remodeling via Inhibiting GSDMD-Mediated Inflammation. Cardiovasc Ther. 2022 Mar 14;2022:3167959. doi: 10.1155/2022/3167959. eCollection 2022. [PubMed:35360548 ]

Showing NP-Card for Oridonin (NP0073109)

MOL for NP0073109 (Oridonin)

3D MOL for NP0073109 (Oridonin)

3D SDF for NP0073109 (Oridonin)

3D-SDF for NP0073109 (Oridonin)

PDB for NP0073109 (Oridonin)

3D PDB for NP0073109 (Oridonin)

SMILES for NP0073109 (Oridonin)

INCHI for NP0073109 (Oridonin)

Structure for NP0073109 (Oridonin)

3D Structure for NP0073109 (Oridonin)