NP-MRD: Showing NP-Card for Vibsanin B (NP0071870)

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Record Information

Version

2.0

Created at

2022-04-28 17:14:37 UTC

Updated at

2022-04-28 17:14:37 UTC

NP-MRD ID

NP0071870

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Vibsanin B

Description

Vibsanin B belongs to the class of organic compounds known as diterpenoids. These are terpene compounds formed by four isoprene units. Vibsanin B is found in Viburnum awabuki, Viburnum odoratissimum and Viburnum suspensum. Vibsanin B was first documented in 2002 (PMID: 12150795). Based on a literature review a significant number of articles have been published on vibsanin B (PMID: 15635234) (PMID: 31542999) (PMID: 29019670) (PMID: 25810397) (PMID: 23724642).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304282219142D          

 30 30  0  0  1  0            999 V2000
    2.3338    1.1614    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3566    0.3368    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9501   -0.3435    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.7171   -1.1349    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.9151   -1.3288    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3463   -0.7312    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5444   -0.9251    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3113   -1.7164    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0244   -0.3275    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2087    0.4639    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0762    0.7139    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5424    1.3945    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.9199    1.9359    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0774    2.7457    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4549    3.2871    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6125    4.0969    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0101    4.6382    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3926    4.3653    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6830    2.2075    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8263   -0.5213    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3951    0.0762    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4998   -1.3955    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9388   -1.9296    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7561   -0.1672    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3118   -0.7769    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0616   -1.5631    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1177   -0.6006    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6734   -1.2103    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4793   -1.0339    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4232   -1.9965    0.0000 C   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  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  7  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
  1 12  1  0  0  0  0
 12 13  1  6  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 16 18  1  0  0  0  0
 12 19  1  1  0  0  0
  9 20  1  0  0  0  0
 20 21  1  0  0  0  0
  4 22  1  1  0  0  0
  4 23  1  6  0  0  0
  3 24  1  1  0  0  0
 24 25  1  0  0  0  0
 25 26  2  0  0  0  0
 25 27  1  0  0  0  0
 27 28  2  0  0  0  0
 28 29  1  0  0  0  0
 28 30  1  0  0  0  0
M  END

     RDKit          3D

 66 66  0  0  0  0  0  0  0  0999 V2000
    4.7722    4.0323   -1.7418 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8689    2.8668   -1.8421 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8259    2.0497   -3.0753 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0944    2.5495   -0.8278 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1514    1.3940   -0.8340 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5356    0.4782    0.2650 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6767   -0.7490    0.3982 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.8452   -1.4566   -0.9614 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1945   -0.4169    0.5499 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4992    0.0381    1.5067 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9627    0.3495    1.6969 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.6071    1.1600    0.8125 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2618    2.3237    1.1349 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2641    2.6632    2.3421 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9138    3.1077    0.1082 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9159    2.7617   -1.1484 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6129    3.6227   -2.1643 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2432    1.5245   -1.6269 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6854   -1.0024    1.7697 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.1695   -0.8455    1.7097 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3609   -1.5639    2.9935 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2206   -1.8824    0.6870 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3666   -2.8383    0.5211 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3825   -3.6258    1.1805 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9878   -4.4364    2.0819 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0151   -3.9094    1.2569 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4278   -5.4399    1.1731 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7649   -5.5560    1.2606 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0016   -3.0899    1.3848 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0866   -1.6741    1.5055 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4866    4.7221   -0.9164 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8275    3.7250   -1.5064 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8322    4.6119   -2.6813 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0594    0.9809   -2.8923 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5886    2.4110   -3.7971 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8594    2.0797   -3.5992 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1333    3.1523    0.0680 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1338    1.8026   -0.7707 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3311    0.8648   -1.8148 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5815    1.0448    1.2412 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5727    0.1371    0.0877 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9617   -1.2124   -1.5862 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7951   -1.1971   -1.4470 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8511   -2.5535   -0.8355 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2186   -0.6089   -0.4841 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0787    0.3787    2.5196 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0732    0.8082    2.6934 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4175    4.0183    0.4099 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9063    3.8148   -2.9868 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5290    3.0857   -2.5059 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8912    4.5982   -1.7235 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3454    1.4296   -2.7405 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1476    1.5449   -1.4391 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7185    0.6234   -1.1643 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7023   -1.5789    2.3823 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4429    0.1560    2.1357 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5948   -0.9742    0.6931 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3945   -1.4554    3.1652 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8072   -1.5633   -0.2748 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5517   -3.1837   -0.6281 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8988   -5.9353    2.0111 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9891   -5.7866    0.2398 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1298   -6.0432    0.4872 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0342   -3.6165    1.3899 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1995   -1.4382    1.6399 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7470   -1.2779    2.5132 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  2  3
  4  5  1  0
  5  6  1  0
  7  6  1  6
  7  8  1  0
  7 30  1  0
 30 29  1  0
 29 26  2  0
 26 27  1  0
 27 28  1  0
 26 24  1  0
 24 25  2  0
 24 23  1  0
 23 22  2  0
 22 19  1  0
 19 20  1  0
 19 21  1  1
 19 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  2  0
 13 15  1  0
 15 16  2  3
 16 17  1  0
 16 18  1  0
 11 10  1  0
 10  9  2  0
  9  7  1  0
  1 31  1  0
  1 32  1  0
  1 33  1  0
  3 34  1  0
  3 35  1  0
  3 36  1  0
  4 37  1  0
  5 38  1  0
  5 39  1  0
  6 40  1  0
  6 41  1  0
  8 42  1  0
  8 43  1  0
  8 44  1  0
 30 65  1  0
 30 66  1  0
 29 64  1  0
 27 61  1  0
 27 62  1  0
 28 63  1  0
 23 60  1  0
 22 59  1  0
 20 55  1  0
 20 56  1  0
 20 57  1  0
 21 58  1  0
 11 47  1  1
 15 48  1  0
 17 49  1  0
 17 50  1  0
 17 51  1  0
 18 52  1  0
 18 53  1  0
 18 54  1  0
 10 46  1  0
  9 45  1  0
M  END


  Mrv1652304282219142D          

 30 30  0  0  1  0            999 V2000
    2.3338    1.1614    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3566    0.3368    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9501   -0.3435    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.7171   -1.1349    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.9151   -1.3288    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3463   -0.7312    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5444   -0.9251    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3113   -1.7164    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0244   -0.3275    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2087    0.4639    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0762    0.7139    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5424    1.3945    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.9199    1.9359    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0774    2.7457    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4549    3.2871    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6125    4.0969    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0101    4.6382    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3926    4.3653    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6830    2.2075    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8263   -0.5213    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3951    0.0762    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4998   -1.3955    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9388   -1.9296    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7561   -0.1672    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3118   -0.7769    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0616   -1.5631    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1177   -0.6006    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6734   -1.2103    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4793   -1.0339    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4232   -1.9965    0.0000 C   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  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  7  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
  1 12  1  0  0  0  0
 12 13  1  6  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 16 18  1  0  0  0  0
 12 19  1  1  0  0  0
  9 20  1  0  0  0  0
 20 21  1  0  0  0  0
  4 22  1  1  0  0  0
  4 23  1  6  0  0  0
  3 24  1  1  0  0  0
 24 25  1  0  0  0  0
 25 26  2  0  0  0  0
 25 27  1  0  0  0  0
 27 28  2  0  0  0  0
 28 29  1  0  0  0  0
 28 30  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0071870

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)=CCC[C@@]1(C)C\C=C(CO)/C(=O)/C=C/[C@@](C)(O)[C@H](OC(=O)C=C(C)C)\C=C\1

> <INCHI_IDENTIFIER>
InChI=1S/C25H36O5/c1-18(2)8-7-12-24(5)13-9-20(17-26)21(27)10-15-25(6,29)22(11-14-24)30-23(28)16-19(3)4/h8-11,14-16,22,26,29H,7,12-13,17H2,1-6H3/b14-11+,15-10+,20-9-/t22-,24+,25-/m1/s1

> <INCHI_KEY>
GYXPHGPELZUVGI-QYGPLFBNSA-N

> <FORMULA>
C25H36O5

> <MOLECULAR_WEIGHT>
416.558

> <EXACT_MASS>
416.256274259

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
66

> <JCHEM_AVERAGE_POLARIZABILITY>
47.07762813241358

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1R,2E,4S,6Z,9E,11R)-11-hydroxy-7-(hydroxymethyl)-4,11-dimethyl-4-(4-methylpent-3-en-1-yl)-8-oxocycloundeca-2,6,9-trien-1-yl 3-methylbut-2-enoate

> <ALOGPS_LOGP>
3.68

> <JCHEM_LOGP>
4.897840207666669

> <ALOGPS_LOGS>
-4.77

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.983407255258903

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.526891120605011

> <JCHEM_PKA_STRONGEST_BASIC>
-2.8132345349290766

> <JCHEM_POLAR_SURFACE_AREA>
83.83000000000001

> <JCHEM_REFRACTIVITY>
124.62959999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
7.01e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1R,2E,4S,6Z,9E,11R)-11-hydroxy-7-(hydroxymethyl)-4,11-dimethyl-4-(4-methylpent-3-en-1-yl)-8-oxocycloundeca-2,6,9-trien-1-yl 3-methylbut-2-enoate

> <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       4.356   2.168   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       4.399   0.629   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       5.507  -0.641   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       5.072  -2.119   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       3.575  -2.480   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.513  -1.365   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.016  -1.727   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       0.581  -3.204   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0      -0.046  -0.611   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.390   0.866   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.009   1.333   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.879   2.603   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.717   3.614   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.011   5.125   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       0.849   6.136   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       1.143   7.648   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -0.019   8.658   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       2.599   8.149   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       3.142   4.121   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -1.542  -0.973   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      -2.604   0.142   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       6.533  -2.605   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       5.486  -3.602   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0       7.011  -0.312   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       8.049  -1.450   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0       7.582  -2.918   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0       9.553  -1.121   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      10.590  -2.259   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      12.095  -1.930   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      10.123  -3.727   0.000  0.00  0.00           C+0
CONECT    1    2   12                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4   24                                                  
CONECT    4    3    5   22   23                                             
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10   20                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11    1   13   19                                             
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16                                                            
CONECT   19   12                                                            
CONECT   20    9   21                                                       
CONECT   21   20                                                            
CONECT   22    4                                                            
CONECT   23    4                                                            
CONECT   24    3   25                                                       
CONECT   25   24   26   27                                                  
CONECT   26   25                                                            
CONECT   27   25   28                                                       
CONECT   28   27   29   30                                                  
CONECT   29   28                                                            
CONECT   30   28                                                            
MASTER        0    0    0    0    0    0    0    0   30    0   60    0
END

View in JSmol

Synonyms

Value	Source
Vibsanine b	ChEBI

Chemical Formula

C₂₅H₃₆O₅

Average Mass

416.5580 Da

Monoisotopic Mass

416.25627 Da

IUPAC Name

(1R,2E,4S,6Z,9E,11R)-11-hydroxy-7-(hydroxymethyl)-4,11-dimethyl-4-(4-methylpent-3-en-1-yl)-8-oxocycloundeca-2,6,9-trien-1-yl 3-methylbut-2-enoate

Traditional Name

(1R,2E,4S,6Z,9E,11R)-11-hydroxy-7-(hydroxymethyl)-4,11-dimethyl-4-(4-methylpent-3-en-1-yl)-8-oxocycloundeca-2,6,9-trien-1-yl 3-methylbut-2-enoate

CAS Registry Number

Not Available

SMILES

CC(C)=CCC[C@@]1(C)C\C=C(CO)/C(=O)/C=C/[C@@](C)(O)[C@H](OC(=O)C=C(C)C)\C=C\1

InChI Identifier

InChI=1S/C25H36O5/c1-18(2)8-7-12-24(5)13-9-20(17-26)21(27)10-15-25(6,29)22(11-14-24)30-23(28)16-19(3)4/h8-11,14-16,22,26,29H,7,12-13,17H2,1-6H3/b14-11+,15-10+,20-9-/t22-,24+,25-/m1/s1

InChI Key

GYXPHGPELZUVGI-QYGPLFBNSA-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
Viburnum awabuki	Plant	KNApSAcK
Viburnum odoratissimum	Plant	KNApSAcK
Viburnum suspensum	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as diterpenoids. These are terpene compounds formed by four isoprene units.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Diterpenoids

Direct Parent

Diterpenoids

Alternative Parents

Substituents

Diterpenoid
Fatty acid ester
Fatty acyl
Tertiary alcohol
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Carboxylic acid ester
Ketone
Cyclic ketone
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Organooxygen compound
Organic oxide
Organic oxygen compound
Alcohol
Primary alcohol
Hydrocarbon derivative
Carbonyl group
Aliphatic homomonocyclic compound

Molecular Framework

Aliphatic homomonocyclic 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	3.68	ALOGPS
logP	4.9	ChemAxon
logS	-4.8	ALOGPS
pKa (Strongest Acidic)	13.53	ChemAxon
pKa (Strongest Basic)	-2.8	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	83.83 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	124.63 m³·mol⁻¹	ChemAxon
Polarizability	47.08 Å³	ChemAxon
Number of Rings	1	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

C00031436

Chemspider ID

24708093

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

15817377

PDB ID

Not Available

ChEBI ID

131781

Good Scents ID

Not Available

References

General References

Fukuyama Y, Kubo M, Minami H, Yuasa H, Matsuo A, Fujii T, Morisaki M, Harada K: Rearranged vibsane-type diterpenes from Viburnum awabuki and photochemical reaction of vibsanin B. Chem Pharm Bull (Tokyo). 2005 Jan;53(1):72-80. doi: 10.1248/cpb.53.72. [PubMed:15635234 ]
He Q, Chu H, Wang Y, Guo H, Wang Y, Wang S, Feng Z, Xie XQ, Hu Y, Liu H, Lin Z: In silico design novel vibsanin B derivatives as inhibitor for heat shock protein 90 based on 3D-QSAR, molecular docking and molecular dynamics simulation. J Biomol Struct Dyn. 2020 Sep;38(14):4313-4324. doi: 10.1080/07391102.2019.1671900. Epub 2019 Oct 3. [PubMed:31542999 ]
Shao LD, Su J, Ye B, Liu JX, Zuo ZL, Li Y, Wang YY, Xia C, Zhao QS: Design, Synthesis, and Biological Activities of Vibsanin B Derivatives: A New Class of HSP90 C-Terminal Inhibitors. J Med Chem. 2017 Nov 9;60(21):9053-9066. doi: 10.1021/acs.jmedchem.7b01395. Epub 2017 Oct 24. [PubMed:29019670 ]
Ye BX, Deng X, Shao LD, Lu Y, Xiao R, Liu YJ, Jin Y, Xie YY, Zhao Y, Luo LF, Ma S, Gao M, Zhang LR, He J, Zhang WN, Chen Y, Xia CF, Deng M, Liu TX, Zhao QS, Chen SJ, Chen Z: Vibsanin B preferentially targets HSP90beta, inhibits interstitial leukocyte migration, and ameliorates experimental autoimmune encephalomyelitis. J Immunol. 2015 May 1;194(9):4489-97. doi: 10.4049/jimmunol.1402798. Epub 2015 Mar 25. [PubMed:25810397 ]
Liu J, Zhou WB, Cong YW, Liu P: [Chemistry and biological activities of Viburnum odoratissimum]. Yao Xue Xue Bao. 2013 Mar;48(3):325-32. [PubMed:23724642 ]
Fukuyama Y, Minami H, Fujii H, Tajima M: Triterpenoids from Viburnum suspensum. Phytochemistry. 2002 Aug;60(8):765-8. doi: 10.1016/s0031-9422(02)00153-x. [PubMed:12150795 ]

Showing NP-Card for Vibsanin B (NP0071870)

MOL for NP0071870 (Vibsanin B)

3D MOL for NP0071870 (Vibsanin B)

3D SDF for NP0071870 (Vibsanin B)

3D-SDF for NP0071870 (Vibsanin B)

PDB for NP0071870 (Vibsanin B)

3D PDB for NP0071870 (Vibsanin B)

SMILES for NP0071870 (Vibsanin B)

INCHI for NP0071870 (Vibsanin B)

Structure for NP0071870 (Vibsanin B)

3D Structure for NP0071870 (Vibsanin B)