NP-MRD: Showing NP-Card for hubeirubesin B (NP0042310)

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Record Information

Version

2.0

Created at

2021-06-21 00:00:07 UTC

Updated at

2021-06-30 00:17:19 UTC

NP-MRD ID

NP0042310

Secondary Accession Numbers

None

Natural Product Identification

Common Name

hubeirubesin B

Provided By

JEOL Database JEOL Logo

Description

Hubeirubesin B 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. hubeirubesin B is found in Isodon rubescens. hubeirubesin B was first documented in 2013 (Liu, X., et al.). Based on a literature review very few articles have been published on Hubeirubesin B.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306212102003D          

 62 65  0  0  0  0            999 V2000
    2.6344   -1.5780    3.7771 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8455   -0.7154    3.1215 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8996    0.2617    3.7894 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.4494   -0.4027    4.0671 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.0492   -1.0830    2.8292 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.8227   -0.3474    1.4751 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.1010    0.4335    0.9203 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.5904    1.4943    1.9274 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2574   -0.5875    0.6891 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.4535   -0.0189   -0.0600 C   0  0  2  0  0  0  0  0  0  0  0  0
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    3.5664    4.0833    3.2350 H   0  0  0  0  0  0  0  0  0  0  0  0
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  6 38  1  6  0  0  0
  7 16  1  0  0  0  0
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 18 19  2  0  0  0  0
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  4  5  1  0  0  0  0
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M  END

     RDKit          3D

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M  END


  Mrv1652306212102003D          

 62 65  0  0  0  0            999 V2000
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    0.5449    0.4481    1.4532 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.7853   -0.5011    1.6172 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.5720   -1.7390    0.9290 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6728   -2.3383    0.4011 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2656   -3.5815   -0.3296 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8273   -1.9525    0.5061 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7132    1.3328    2.7037 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.9123    2.1371    2.6646 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7677    3.4362    2.2911 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1019    4.1132    2.2463 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7026    3.9742    2.0245 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3248   -2.2290    3.2487 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6255   -1.6425    4.8607 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3356    0.6848    4.7010 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.1482    0.3514    4.4473 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.5849   -2.0756    2.7430 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7038   -1.1573    0.7392 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9402    2.3672    1.9813 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5868    1.8707    1.6957 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6761    1.0788    2.9349 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6254   -0.9847    1.6408 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8739   -1.4460    0.1213 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9856    0.7428    0.5158 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1676   -0.8285   -0.2522 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5968    2.4539   -2.9641 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1879    1.9775   -3.5302 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9735    0.7389   -3.2170 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1513    3.3021   -1.7038 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9182    2.9402   -0.0159 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6129    3.6994   -0.9389 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3249    0.1457   -1.0487 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2420    2.3878   -1.3330 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7449    2.8343    0.2840 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7094   -0.0061    1.2922 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1470   -4.0368   -0.7901 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8274   -4.2960    0.3716 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5532   -3.3307   -1.1198 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1467    1.9612    2.9379 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9678    5.1591    1.9558 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7398    3.6242    1.5058 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5664    4.0833    3.2350 H   0  0  0  0  0  0  0  0  0  0  0  0
 17 18  1  0  0  0  0
 16 52  1  6  0  0  0
 10 11  1  0  0  0  0
 20 18  1  6  0  0  0
 13 14  1  6  0  0  0
  7  9  1  0  0  0  0
 13 15  1  0  0  0  0
 20 26  1  0  0  0  0
  6 38  1  6  0  0  0
  7 16  1  0  0  0  0
  3  2  1  0  0  0  0
  3  4  1  0  0  0  0
 18 19  2  0  0  0  0
 20 21  1  0  0  0  0
  4  5  1  0  0  0  0
 26 27  1  0  0  0  0
 21  2  1  0  0  0  0
  3 26  1  0  0  0  0
  2  1  2  3  0  0  0
 10  9  1  0  0  0  0
 21 22  1  0  0  0  0
 11 13  1  0  0  0  0
 22 23  1  0  0  0  0
 13 16  1  0  0  0  0
 23 24  1  0  0  0  0
  7  8  1  1  0  0  0
 23 25  2  0  0  0  0
  5  6  1  0  0  0  0
 27 28  1  0  0  0  0
 20  6  1  0  0  0  0
 28 29  1  0  0  0  0
 16 17  1  0  0  0  0
 28 30  2  0  0  0  0
  7  6  1  0  0  0  0
 11 12  2  0  0  0  0
 10 44  1  0  0  0  0
 10 45  1  0  0  0  0
  9 42  1  0  0  0  0
  9 43  1  0  0  0  0
 17 53  1  0  0  0  0
 17 54  1  0  0  0  0
  4 34  1  0  0  0  0
  4 35  1  0  0  0  0
  5 36  1  0  0  0  0
  5 37  1  0  0  0  0
  3 33  1  1  0  0  0
 26 59  1  1  0  0  0
  8 39  1  0  0  0  0
  8 40  1  0  0  0  0
  8 41  1  0  0  0  0
 14 46  1  0  0  0  0
 14 47  1  0  0  0  0
 14 48  1  0  0  0  0
 15 49  1  0  0  0  0
 15 50  1  0  0  0  0
 15 51  1  0  0  0  0
 21 55  1  6  0  0  0
  1 31  1  0  0  0  0
  1 32  1  0  0  0  0
 24 56  1  0  0  0  0
 24 57  1  0  0  0  0
 24 58  1  0  0  0  0
 29 60  1  0  0  0  0
 29 61  1  0  0  0  0
 29 62  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0042310

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]C([H])=C1[C@@]([H])(OC(=O)C([H])([H])[H])[C@@]23C(=O)C([H])([H])[C@]4([H])C(C(=O)C([H])([H])C([H])([H])[C@@]4(C([H])([H])[H])[C@]2([H])C([H])([H])C([H])([H])[C@]1([H])[C@@]3([H])OC(=O)C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C24H32O6/c1-12-15-7-8-16-23(6)10-9-18(27)22(4,5)17(23)11-19(28)24(16,20(12)29-13(2)25)21(15)30-14(3)26/h15-17,20-21H,1,7-11H2,2-6H3/t15-,16-,17+,20+,21+,23-,24-/m0/s1

> <INCHI_KEY>
PRDQFMINXHTSBP-VWJSVJFPSA-N

> <FORMULA>
C24H32O6

> <MOLECULAR_WEIGHT>
416.514

> <EXACT_MASS>
416.21988875

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
62

> <JCHEM_AVERAGE_POLARIZABILITY>
44.424641100054885

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1R,4S,9R,10S,13S,15R,16R)-15-(acetyloxy)-5,5,9-trimethyl-14-methylidene-2,6-dioxotetracyclo[11.2.1.0^{1,10}.0^{4,9}]hexadecan-16-yl acetate

> <ALOGPS_LOGP>
2.16

> <JCHEM_LOGP>
2.936061319333334

> <ALOGPS_LOGS>
-4.31

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
18.61529975425582

> <JCHEM_PKA_STRONGEST_BASIC>
-6.594632736518869

> <JCHEM_POLAR_SURFACE_AREA>
86.74000000000001

> <JCHEM_REFRACTIVITY>
108.13579999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.02e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1R,4S,9R,10S,13S,15R,16R)-15-(acetyloxy)-5,5,9-trimethyl-14-methylidene-2,6-dioxotetracyclo[11.2.1.0^{1,10}.0^{4,9}]hexadecan-16-yl acetate

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 62 65  0  0  0  0  0  0  0  0999 V2000
    2.6344   -1.5780    3.7771 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8455   -0.7154    3.1215 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8996    0.2617    3.7894 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.4494   -0.4027    4.0671 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0492   -1.0830    2.8292 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8227   -0.3474    1.4751 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.1010    0.4335    0.9203 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.5904    1.4943    1.9274 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2574   -0.5875    0.6891 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4535   -0.0189   -0.0600 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0395    0.5710   -1.3833 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6900    0.3106   -2.3971 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8703    1.5689   -1.3878 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.3738    1.6921   -2.8527 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4076    2.9479   -0.9787 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7085    1.0161   -0.4891 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.5250    1.9806   -0.3578 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6899    1.2546    0.1702 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7708    1.3858   -0.4070 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5449    0.4481    1.4532 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.7853   -0.5011    1.6172 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.5720   -1.7390    0.9290 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6728   -2.3383    0.4011 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2656   -3.5815   -0.3296 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8273   -1.9525    0.5061 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7132    1.3328    2.7037 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.9123    2.1371    2.6646 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7677    3.4362    2.2911 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1019    4.1132    2.2463 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7026    3.9742    2.0245 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3248   -2.2290    3.2487 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6255   -1.6425    4.8607 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3356    0.6848    4.7010 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.1482    0.3514    4.4473 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.5849   -2.0756    2.7430 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7038   -1.1573    0.7392 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9402    2.3672    1.9813 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -3.6254   -0.9847    1.6408 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -4.9856    0.7428    0.5158 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1676   -0.8285   -0.2522 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5968    2.4539   -2.9641 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1879    1.9775   -3.5302 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9735    0.7389   -3.2170 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1513    3.3021   -1.7038 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9182    2.9402   -0.0159 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6129    3.6994   -0.9389 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3249    0.1457   -1.0487 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2420    2.3878   -1.3330 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7449    2.8343    0.2840 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7094   -0.0061    1.2922 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1470   -4.0368   -0.7901 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8274   -4.2960    0.3716 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5532   -3.3307   -1.1198 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1467    1.9612    2.9379 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9678    5.1591    1.9558 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7398    3.6242    1.5058 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5664    4.0833    3.2350 H   0  0  0  0  0  0  0  0  0  0  0  0
 17 18  1  0
 16 52  1  6
 10 11  1  0
 20 18  1  6
 13 14  1  6
  7  9  1  0
 13 15  1  0
 20 26  1  0
  6 38  1  6
  7 16  1  0
  3  2  1  0
  3  4  1  0
 18 19  2  0
 20 21  1  0
  4  5  1  0
 26 27  1  0
 21  2  1  0
  3 26  1  0
  2  1  2  3
 10  9  1  0
 21 22  1  0
 11 13  1  0
 22 23  1  0
 13 16  1  0
 23 24  1  0
  7  8  1  1
 23 25  2  0
  5  6  1  0
 27 28  1  0
 20  6  1  0
 28 29  1  0
 16 17  1  0
 28 30  2  0
  7  6  1  0
 11 12  2  0
 10 44  1  0
 10 45  1  0
  9 42  1  0
  9 43  1  0
 17 53  1  0
 17 54  1  0
  4 34  1  0
  4 35  1  0
  5 36  1  0
  5 37  1  0
  3 33  1  1
 26 59  1  1
  8 39  1  0
  8 40  1  0
  8 41  1  0
 14 46  1  0
 14 47  1  0
 14 48  1  0
 15 49  1  0
 15 50  1  0
 15 51  1  0
 21 55  1  6
  1 31  1  0
  1 32  1  0
 24 56  1  0
 24 57  1  0
 24 58  1  0
 29 60  1  0
 29 61  1  0
 29 62  1  0
M  END

HEADER    PROTEIN                                 21-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   21-JUN-21         0                                  
HETATM    1  C   UNK     0       2.634  -1.578   3.777  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.845  -0.715   3.122  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.900   0.262   3.789  0.00  0.00           C+0
HETATM    4  C   UNK     0      -0.449  -0.403   4.067  0.00  0.00           C+0
HETATM    5  C   UNK     0      -1.049  -1.083   2.829  0.00  0.00           C+0
HETATM    6  C   UNK     0      -0.823  -0.347   1.475  0.00  0.00           C+0
HETATM    7  C   UNK     0      -2.101   0.434   0.920  0.00  0.00           C+0
HETATM    8  C   UNK     0      -2.590   1.494   1.927  0.00  0.00           C+0
HETATM    9  C   UNK     0      -3.257  -0.588   0.689  0.00  0.00           C+0
HETATM   10  C   UNK     0      -4.454  -0.019  -0.060  0.00  0.00           C+0
HETATM   11  C   UNK     0      -4.040   0.571  -1.383  0.00  0.00           C+0
HETATM   12  O   UNK     0      -4.690   0.311  -2.397  0.00  0.00           O+0
HETATM   13  C   UNK     0      -2.870   1.569  -1.388  0.00  0.00           C+0
HETATM   14  C   UNK     0      -2.374   1.692  -2.853  0.00  0.00           C+0
HETATM   15  C   UNK     0      -3.408   2.948  -0.979  0.00  0.00           C+0
HETATM   16  C   UNK     0      -1.708   1.016  -0.489  0.00  0.00           C+0
HETATM   17  C   UNK     0      -0.525   1.981  -0.358  0.00  0.00           C+0
HETATM   18  C   UNK     0       0.690   1.255   0.170  0.00  0.00           C+0
HETATM   19  O   UNK     0       1.771   1.386  -0.407  0.00  0.00           O+0
HETATM   20  C   UNK     0       0.545   0.448   1.453  0.00  0.00           C+0
HETATM   21  C   UNK     0       1.785  -0.501   1.617  0.00  0.00           C+0
HETATM   22  O   UNK     0       1.572  -1.739   0.929  0.00  0.00           O+0
HETATM   23  C   UNK     0       2.673  -2.338   0.401  0.00  0.00           C+0
HETATM   24  C   UNK     0       2.266  -3.582  -0.330  0.00  0.00           C+0
HETATM   25  O   UNK     0       3.827  -1.952   0.506  0.00  0.00           O+0
HETATM   26  C   UNK     0       0.713   1.333   2.704  0.00  0.00           C+0
HETATM   27  O   UNK     0       1.912   2.137   2.665  0.00  0.00           O+0
HETATM   28  C   UNK     0       1.768   3.436   2.291  0.00  0.00           C+0
HETATM   29  C   UNK     0       3.102   4.113   2.246  0.00  0.00           C+0
HETATM   30  O   UNK     0       0.703   3.974   2.025  0.00  0.00           O+0
HETATM   31  H   UNK     0       3.325  -2.229   3.249  0.00  0.00           H+0
HETATM   32  H   UNK     0       2.626  -1.643   4.861  0.00  0.00           H+0
HETATM   33  H   UNK     0       1.336   0.685   4.701  0.00  0.00           H+0
HETATM   34  H   UNK     0      -0.345  -1.149   4.865  0.00  0.00           H+0
HETATM   35  H   UNK     0      -1.148   0.351   4.447  0.00  0.00           H+0
HETATM   36  H   UNK     0      -2.104  -1.294   3.023  0.00  0.00           H+0
HETATM   37  H   UNK     0      -0.585  -2.076   2.743  0.00  0.00           H+0
HETATM   38  H   UNK     0      -0.704  -1.157   0.739  0.00  0.00           H+0
HETATM   39  H   UNK     0      -1.940   2.367   1.981  0.00  0.00           H+0
HETATM   40  H   UNK     0      -3.587   1.871   1.696  0.00  0.00           H+0
HETATM   41  H   UNK     0      -2.676   1.079   2.935  0.00  0.00           H+0
HETATM   42  H   UNK     0      -3.625  -0.985   1.641  0.00  0.00           H+0
HETATM   43  H   UNK     0      -2.874  -1.446   0.121  0.00  0.00           H+0
HETATM   44  H   UNK     0      -4.986   0.743   0.516  0.00  0.00           H+0
HETATM   45  H   UNK     0      -5.168  -0.829  -0.252  0.00  0.00           H+0
HETATM   46  H   UNK     0      -1.597   2.454  -2.964  0.00  0.00           H+0
HETATM   47  H   UNK     0      -3.188   1.978  -3.530  0.00  0.00           H+0
HETATM   48  H   UNK     0      -1.974   0.739  -3.217  0.00  0.00           H+0
HETATM   49  H   UNK     0      -4.151   3.302  -1.704  0.00  0.00           H+0
HETATM   50  H   UNK     0      -3.918   2.940  -0.016  0.00  0.00           H+0
HETATM   51  H   UNK     0      -2.613   3.699  -0.939  0.00  0.00           H+0
HETATM   52  H   UNK     0      -1.325   0.146  -1.049  0.00  0.00           H+0
HETATM   53  H   UNK     0      -0.242   2.388  -1.333  0.00  0.00           H+0
HETATM   54  H   UNK     0      -0.745   2.834   0.284  0.00  0.00           H+0
HETATM   55  H   UNK     0       2.709  -0.006   1.292  0.00  0.00           H+0
HETATM   56  H   UNK     0       3.147  -4.037  -0.790  0.00  0.00           H+0
HETATM   57  H   UNK     0       1.827  -4.296   0.372  0.00  0.00           H+0
HETATM   58  H   UNK     0       1.553  -3.331  -1.120  0.00  0.00           H+0
HETATM   59  H   UNK     0      -0.147   1.961   2.938  0.00  0.00           H+0
HETATM   60  H   UNK     0       2.968   5.159   1.956  0.00  0.00           H+0
HETATM   61  H   UNK     0       3.740   3.624   1.506  0.00  0.00           H+0
HETATM   62  H   UNK     0       3.566   4.083   3.235  0.00  0.00           H+0
CONECT    1    2   31   32                                                  
CONECT    2    3   21    1                                                  
CONECT    3    2    4   26   33                                             
CONECT    4    3    5   34   35                                             
CONECT    5    4    6   36   37                                             
CONECT    6   38    5   20    7                                             
CONECT    7    9   16    8    6                                             
CONECT    8    7   39   40   41                                             
CONECT    9    7   10   42   43                                             
CONECT   10   11    9   44   45                                             
CONECT   11   10   13   12                                                  
CONECT   12   11                                                            
CONECT   13   14   15   11   16                                             
CONECT   14   13   46   47   48                                             
CONECT   15   13   49   50   51                                             
CONECT   16   52    7   13   17                                             
CONECT   17   18   16   53   54                                             
CONECT   18   17   20   19                                                  
CONECT   19   18                                                            
CONECT   20   18   26   21    6                                             
CONECT   21   20    2   22   55                                             
CONECT   22   21   23                                                       
CONECT   23   22   24   25                                                  
CONECT   24   23   56   57   58                                             
CONECT   25   23                                                            
CONECT   26   20   27    3   59                                             
CONECT   27   26   28                                                       
CONECT   28   27   29   30                                                  
CONECT   29   28   60   61   62                                             
CONECT   30   28                                                            
CONECT   31    1                                                            
CONECT   32    1                                                            
CONECT   33    3                                                            
CONECT   34    4                                                            
CONECT   35    4                                                            
CONECT   36    5                                                            
CONECT   37    5                                                            
CONECT   38    6                                                            
CONECT   39    8                                                            
CONECT   40    8                                                            
CONECT   41    8                                                            
CONECT   42    9                                                            
CONECT   43    9                                                            
CONECT   44   10                                                            
CONECT   45   10                                                            
CONECT   46   14                                                            
CONECT   47   14                                                            
CONECT   48   14                                                            
CONECT   49   15                                                            
CONECT   50   15                                                            
CONECT   51   15                                                            
CONECT   52   16                                                            
CONECT   53   17                                                            
CONECT   54   17                                                            
CONECT   55   21                                                            
CONECT   56   24                                                            
CONECT   57   24                                                            
CONECT   58   24                                                            
CONECT   59   26                                                            
CONECT   60   29                                                            
CONECT   61   29                                                            
CONECT   62   29                                                            
MASTER        0    0    0    0    0    0    0    0   62    0  130    0
END

RDKit          3D

62 65  0  0  0  0  0  0  0  0999 V2000
    2.6344   -1.5780    3.7771 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8455   -0.7154    3.1215 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8996    0.2617    3.7894 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.4494   -0.4027    4.0671 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0492   -1.0830    2.8292 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8227   -0.3474    1.4751 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.1010    0.4335    0.9203 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.5904    1.4943    1.9274 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2574   -0.5875    0.6891 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4535   -0.0189   -0.0600 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0395    0.5710   -1.3833 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6900    0.3106   -2.3971 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8703    1.5689   -1.3878 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.3738    1.6921   -2.8527 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4076    2.9479   -0.9787 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7085    1.0161   -0.4891 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.5250    1.9806   -0.3578 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6899    1.2546    0.1702 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7708    1.3858   -0.4070 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5449    0.4481    1.4532 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.7853   -0.5011    1.6172 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.5720   -1.7390    0.9290 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6728   -2.3383    0.4011 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2656   -3.5815   -0.3296 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8273   -1.9525    0.5061 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7132    1.3328    2.7037 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.9123    2.1371    2.6646 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7677    3.4362    2.2911 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1019    4.1132    2.2463 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7026    3.9742    2.0245 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3248   -2.2290    3.2487 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6255   -1.6425    4.8607 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3356    0.6848    4.7010 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3452   -1.1485    4.8653 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1482    0.3514    4.4473 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1037   -1.2935    3.0226 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5849   -2.0756    2.7430 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7038   -1.1573    0.7392 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9402    2.3672    1.9813 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5868    1.8707    1.6957 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6761    1.0788    2.9349 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6254   -0.9847    1.6408 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8739   -1.4460    0.1213 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9856    0.7428    0.5158 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1676   -0.8285   -0.2522 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5968    2.4539   -2.9641 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1879    1.9775   -3.5302 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9735    0.7389   -3.2170 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1513    3.3021   -1.7038 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9182    2.9402   -0.0159 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6129    3.6994   -0.9389 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3249    0.1457   -1.0487 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2420    2.3878   -1.3330 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7449    2.8343    0.2840 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7094   -0.0061    1.2922 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1470   -4.0368   -0.7901 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8274   -4.2960    0.3716 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5532   -3.3307   -1.1198 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1467    1.9612    2.9379 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9678    5.1591    1.9558 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7398    3.6242    1.5058 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5664    4.0833    3.2350 H   0  0  0  0  0  0  0  0  0  0  0  0
 17 18  1  0
 16 52  1  6
 10 11  1  0
 20 18  1  6
 13 14  1  6
  7  9  1  0
 13 15  1  0
 20 26  1  0
  6 38  1  6
  7 16  1  0
  3  2  1  0
  3  4  1  0
 18 19  2  0
 20 21  1  0
  4  5  1  0
 26 27  1  0
 21  2  1  0
  3 26  1  0
  2  1  2  3
 10  9  1  0
 21 22  1  0
 11 13  1  0
 22 23  1  0
 13 16  1  0
 23 24  1  0
  7  8  1  1
 23 25  2  0
  5  6  1  0
 27 28  1  0
 20  6  1  0
 28 29  1  0
 16 17  1  0
 28 30  2  0
  7  6  1  0
 11 12  2  0
 10 44  1  0
 10 45  1  0
  9 42  1  0
  9 43  1  0
 17 53  1  0
 17 54  1  0
  4 34  1  0
  4 35  1  0
  5 36  1  0
  5 37  1  0
  3 33  1  1
 26 59  1  1
  8 39  1  0
  8 40  1  0
  8 41  1  0
 14 46  1  0
 14 47  1  0
 14 48  1  0
 15 49  1  0
 15 50  1  0
 15 51  1  0
 21 55  1  6
  1 31  1  0
  1 32  1  0
 24 56  1  0
 24 57  1  0
 24 58  1  0
 29 60  1  0
 29 61  1  0
 29 62  1  0
M  END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₄H₃₂O₆

Average Mass

416.5140 Da

Monoisotopic Mass

416.21989 Da

IUPAC Name

(1R,4S,9R,10S,13S,15R,16R)-15-(acetyloxy)-5,5,9-trimethyl-14-methylidene-2,6-dioxotetracyclo[11.2.1.0^{1,10}.0^{4,9}]hexadecan-16-yl acetate

Traditional Name

(1R,4S,9R,10S,13S,15R,16R)-15-(acetyloxy)-5,5,9-trimethyl-14-methylidene-2,6-dioxotetracyclo[11.2.1.0^{1,10}.0^{4,9}]hexadecan-16-yl acetate

CAS Registry Number

Not Available

SMILES

[H]C([H])=C1[C@@]([H])(OC(=O)C([H])([H])[H])[C@@]23C(=O)C([H])([H])[C@]4([H])C(C(=O)C([H])([H])C([H])([H])[C@@]4(C([H])([H])[H])[C@]2([H])C([H])([H])C([H])([H])[C@]1([H])[C@@]3([H])OC(=O)C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H]

InChI Identifier

InChI=1S/C24H32O6/c1-12-15-7-8-16-23(6)10-9-18(27)22(4,5)17(23)11-19(28)24(16,20(12)29-13(2)25)21(15)30-14(3)26/h15-17,20-21H,1,7-11H2,2-6H3/t15-,16-,17+,20+,21+,23-,24-/m0/s1

InChI Key

PRDQFMINXHTSBP-VWJSVJFPSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Isodon rubescens	JEOL database	Liu, X., et al., Chem. Pharm. Bull. 61, 90 (2013)

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
Dicarboxylic acid or derivatives
Cyclic ketone
Ketone
Carboxylic acid ester
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic 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	2.16	ALOGPS
logP	2.94	ChemAxon
logS	-4.3	ALOGPS
pKa (Strongest Acidic)	18.62	ChemAxon
pKa (Strongest Basic)	-6.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	86.74 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	108.14 m³·mol⁻¹	ChemAxon
Polarizability	44.42 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

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

71530363

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Liu, X., et al. (2013). Liu, X., et al., Chem. Pharm. Bull. 61, 90 (2013). Chem. Pharm. Bull..

Showing NP-Card for hubeirubesin B (NP0042310)

MOL for NP0042310 (hubeirubesin B)

3D MOL for NP0042310 (hubeirubesin B)

3D SDF for NP0042310 (hubeirubesin B)

3D-SDF for NP0042310 (hubeirubesin B)

PDB for NP0042310 (hubeirubesin B)

3D PDB for NP0042310 (hubeirubesin B)

SMILES for NP0042310 (hubeirubesin B)

INCHI for NP0042310 (hubeirubesin B)

Structure for NP0042310 (hubeirubesin B)

3D Structure for NP0042310 (hubeirubesin B)