NP-MRD: Showing NP-Card for Bisabosqual B (NP0003992)

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Record Information

Version

1.0

Created at

2020-12-09 01:31:11 UTC

Updated at

2021-07-15 16:47:56 UTC

NP-MRD ID

NP0003992

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Bisabosqual B

Provided By

NPAtlas

Description

Bisabosqual B is found in Stachybotrys and Stachybotrys ruwenzoriensis RF6853. It was first documented in 2001 (PMID: 11827030). Based on a literature review very few articles have been published on (7S,8R,11S,12R,13S)-11-hydroxy-3-(hydroxymethyl)-7,11-dimethyl-7-(4-methylpent-3-en-1-yl)-6,15-dioxatetracyclo[10.2.1.0⁵,¹⁴.0⁸,¹³]Pentadeca-1,3,5(14)-triene-2-carbaldehyde (PMID: 26149533) (PMID: 11827031).

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306242118033D          

 58 61  0  0  0  0            999 V2000
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M  END

     RDKit          3D

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M  END


  Mrv1652306242118033D          

 58 61  0  0  0  0            999 V2000
    6.6660    0.8597    1.2994 C   0  0  0  0  0  0  0  0  0  0  0  0
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    7.2455    0.9105    0.3617 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0759    0.1039    1.9959 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6506    1.8287    1.8087 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2384   -1.4629    1.2418 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0568   -1.2126   -0.4146 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9837   -1.5472    1.0778 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7967    2.4442    0.9580 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8791    2.0682   -0.5619 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4304    2.1077    1.1700 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8479   -0.4869   -0.4507 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2544   -0.3977    1.2472 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7339    0.7816   -2.0935 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9627    2.1091   -1.2419 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1183    0.9223   -1.9464 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3937    3.3188    1.0282 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7390    3.3836    2.0147 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8382    3.4923    0.2332 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2998    5.0204    0.2496 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8134    0.7401    1.8674 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8007   -1.5035    1.7059 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1207   -3.0793    0.7887 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4627   -4.3869   -2.3090 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3002   -4.4981   -0.5407 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8039   -4.1492   -1.5549 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7404   -2.9141   -2.4363 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8185   -0.7238   -2.3175 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2505   -2.2100   -3.0934 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5300   -2.5813   -1.7069 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6515   -0.9188   -2.2853 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9281   -1.7518    0.3097 H   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
  2  4  2  3  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  7  6  1  1  0  0  0
  7  8  1  0  0  0  0
  7  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 12 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 15 18  1  0  0  0  0
 18 19  2  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 21 23  1  0  0  0  0
 23 24  1  0  0  0  0
 23 25  1  6  0  0  0
 23 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28  7  1  0  0  0  0
 19 10  1  0  0  0  0
 28 20  1  0  0  0  0
 22 18  1  0  0  0  0
  1 29  1  0  0  0  0
  1 30  1  0  0  0  0
  1 31  1  0  0  0  0
  3 32  1  0  0  0  0
  3 33  1  0  0  0  0
  3 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
  6 38  1  0  0  0  0
  6 39  1  0  0  0  0
  8 40  1  0  0  0  0
  8 41  1  0  0  0  0
  8 42  1  0  0  0  0
 11 43  1  0  0  0  0
 13 44  1  0  0  0  0
 13 45  1  0  0  0  0
 14 46  1  0  0  0  0
 16 47  1  0  0  0  0
 20 48  1  1  0  0  0
 21 49  1  1  0  0  0
 24 50  1  0  0  0  0
 24 51  1  0  0  0  0
 24 52  1  0  0  0  0
 25 53  1  0  0  0  0
 26 54  1  0  0  0  0
 26 55  1  0  0  0  0
 27 56  1  0  0  0  0
 27 57  1  0  0  0  0
 28 58  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0003992

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC([H])([H])C1=C(C([H])=O)C2=C3C(O[C@@](C([H])([H])[H])(C([H])([H])C([H])([H])C([H])=C(C([H])([H])[H])C([H])([H])[H])[C@]4([H])C([H])([H])C([H])([H])[C@@](O[H])(C([H])([H])[H])[C@]([H])(O2)[C@]34[H])=C1[H]

> <INCHI_IDENTIFIER>
InChI=1S/C23H30O5/c1-13(2)6-5-8-23(4)16-7-9-22(3,26)21-18(16)19-17(28-23)10-14(11-24)15(12-25)20(19)27-21/h6,10,12,16,18,21,24,26H,5,7-9,11H2,1-4H3/t16-,18+,21-,22+,23+/m1/s1

> <INCHI_KEY>
PJUNMTHNNQPMQB-MQRVUQIVSA-N

> <FORMULA>
C23H30O5

> <MOLECULAR_WEIGHT>
386.488

> <EXACT_MASS>
386.209324066

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
58

> <JCHEM_AVERAGE_POLARIZABILITY>
43.315293062843736

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(7S,8R,11S,12R,13S)-11-hydroxy-3-(hydroxymethyl)-7,11-dimethyl-7-(4-methylpent-3-en-1-yl)-6,15-dioxatetracyclo[10.2.1.0^{5,14}.0^{8,13}]pentadeca-1(14),2,4-triene-2-carbaldehyde

> <ALOGPS_LOGP>
2.96

> <JCHEM_LOGP>
3.0152214143333325

> <ALOGPS_LOGS>
-4.47

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.724034337265554

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.9213623665979

> <JCHEM_PKA_STRONGEST_BASIC>
-2.9627716851416883

> <JCHEM_POLAR_SURFACE_AREA>
75.99000000000001

> <JCHEM_REFRACTIVITY>
108.8284

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.31e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(7S,8R,11S,12R,13S)-11-hydroxy-3-(hydroxymethyl)-7,11-dimethyl-7-(4-methylpent-3-en-1-yl)-6,15-dioxatetracyclo[10.2.1.0^{5,14}.0^{8,13}]pentadeca-1(14),2,4-triene-2-carbaldehyde

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 58 61  0  0  0  0  0  0  0  0999 V2000
    6.6660    0.8597    1.2994 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2352    0.4571    0.8965 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0594   -0.9990    0.6970 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3683    1.4050    0.7584 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9560    1.4623    0.4031 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3173    0.1376    0.2669 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8279    0.2855   -0.1497 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.8509    1.0021   -1.4589 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2489    1.1879    0.8117 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1375    1.2364    0.8393 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8936    2.3868    0.9533 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2866    2.2633    0.9653 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1230    3.4820    1.0868 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3702    4.6300    1.1758 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9026    1.0246    0.8661 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3538    0.8760    0.8766 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0667    0.8955   -0.1465 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1407   -0.1353    0.7513 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7814    0.0552    0.7459 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0513   -1.2163    0.6370 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.1317   -2.1303    0.2061 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.3529   -1.4870    0.6355 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2036   -2.4948   -1.2280 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.8964   -3.9826   -1.4451 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5221   -2.3140   -1.6716 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3148   -1.6718   -2.1236 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0830   -1.5607   -1.5866 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1506   -1.0626   -0.1677 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.2455    0.9105    0.3617 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0759    0.1039    1.9959 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6506    1.8287    1.8087 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2384   -1.4629    1.2418 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0568   -1.2126   -0.4146 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9837   -1.5472    1.0778 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7967    2.4442    0.9580 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8791    2.0682   -0.5619 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4304    2.1077    1.1700 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8479   -0.4869   -0.4507 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2544   -0.3977    1.2472 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7339    0.7816   -2.0935 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9627    2.1091   -1.2419 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1183    0.9223   -1.9464 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3937    3.3188    1.0282 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7390    3.3836    2.0147 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8382    3.4923    0.2332 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2998    5.0204    0.2496 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8134    0.7401    1.8674 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8007   -1.5035    1.7059 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1207   -3.0793    0.7887 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4627   -4.3869   -2.3090 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3002   -4.4981   -0.5407 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8039   -4.1492   -1.5549 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7404   -2.9141   -2.4363 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8185   -0.7238   -2.3175 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2505   -2.2100   -3.0934 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5300   -2.5813   -1.7069 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6515   -0.9188   -2.2853 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9281   -1.7518    0.3097 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  1
  7  8  1  0
  7  9  1  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 12 15  2  0
 15 16  1  0
 16 17  2  0
 15 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 21 23  1  0
 23 24  1  0
 23 25  1  6
 23 26  1  0
 26 27  1  0
 27 28  1  0
 28  7  1  0
 19 10  1  0
 28 20  1  0
 22 18  1  0
  1 29  1  0
  1 30  1  0
  1 31  1  0
  3 32  1  0
  3 33  1  0
  3 34  1  0
  4 35  1  0
  5 36  1  0
  5 37  1  0
  6 38  1  0
  6 39  1  0
  8 40  1  0
  8 41  1  0
  8 42  1  0
 11 43  1  0
 13 44  1  0
 13 45  1  0
 14 46  1  0
 16 47  1  0
 20 48  1  1
 21 49  1  1
 24 50  1  0
 24 51  1  0
 24 52  1  0
 25 53  1  0
 26 54  1  0
 26 55  1  0
 27 56  1  0
 27 57  1  0
 28 58  1  1
M  END

HEADER    PROTEIN                                 24-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-JUN-21         0                                  
HETATM    1  C   UNK     0       6.666   0.860   1.299  0.00  0.00           C+0
HETATM    2  C   UNK     0       5.235   0.457   0.897  0.00  0.00           C+0
HETATM    3  C   UNK     0       5.059  -0.999   0.697  0.00  0.00           C+0
HETATM    4  C   UNK     0       4.368   1.405   0.758  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.956   1.462   0.403  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.317   0.138   0.267  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.828   0.286  -0.150  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.851   1.002  -1.459  0.00  0.00           C+0
HETATM    9  O   UNK     0       0.249   1.188   0.812  0.00  0.00           O+0
HETATM   10  C   UNK     0      -1.137   1.236   0.839  0.00  0.00           C+0
HETATM   11  C   UNK     0      -1.894   2.387   0.953  0.00  0.00           C+0
HETATM   12  C   UNK     0      -3.287   2.263   0.965  0.00  0.00           C+0
HETATM   13  C   UNK     0      -4.123   3.482   1.087  0.00  0.00           C+0
HETATM   14  O   UNK     0      -3.370   4.630   1.176  0.00  0.00           O+0
HETATM   15  C   UNK     0      -3.903   1.025   0.866  0.00  0.00           C+0
HETATM   16  C   UNK     0      -5.354   0.876   0.877  0.00  0.00           C+0
HETATM   17  O   UNK     0      -6.067   0.896  -0.147  0.00  0.00           O+0
HETATM   18  C   UNK     0      -3.141  -0.135   0.751  0.00  0.00           C+0
HETATM   19  C   UNK     0      -1.781   0.055   0.746  0.00  0.00           C+0
HETATM   20  C   UNK     0      -1.051  -1.216   0.637  0.00  0.00           C+0
HETATM   21  C   UNK     0      -2.132  -2.130   0.206  0.00  0.00           C+0
HETATM   22  O   UNK     0      -3.353  -1.487   0.636  0.00  0.00           O+0
HETATM   23  C   UNK     0      -2.204  -2.495  -1.228  0.00  0.00           C+0
HETATM   24  C   UNK     0      -1.896  -3.983  -1.445  0.00  0.00           C+0
HETATM   25  O   UNK     0      -3.522  -2.314  -1.672  0.00  0.00           O+0
HETATM   26  C   UNK     0      -1.315  -1.672  -2.124  0.00  0.00           C+0
HETATM   27  C   UNK     0       0.083  -1.561  -1.587  0.00  0.00           C+0
HETATM   28  C   UNK     0       0.151  -1.063  -0.168  0.00  0.00           C+0
HETATM   29  H   UNK     0       7.245   0.911   0.362  0.00  0.00           H+0
HETATM   30  H   UNK     0       7.076   0.104   1.996  0.00  0.00           H+0
HETATM   31  H   UNK     0       6.651   1.829   1.809  0.00  0.00           H+0
HETATM   32  H   UNK     0       4.238  -1.463   1.242  0.00  0.00           H+0
HETATM   33  H   UNK     0       5.057  -1.213  -0.415  0.00  0.00           H+0
HETATM   34  H   UNK     0       5.984  -1.547   1.078  0.00  0.00           H+0
HETATM   35  H   UNK     0       4.797   2.444   0.958  0.00  0.00           H+0
HETATM   36  H   UNK     0       2.879   2.068  -0.562  0.00  0.00           H+0
HETATM   37  H   UNK     0       2.430   2.108   1.170  0.00  0.00           H+0
HETATM   38  H   UNK     0       2.848  -0.487  -0.451  0.00  0.00           H+0
HETATM   39  H   UNK     0       2.254  -0.398   1.247  0.00  0.00           H+0
HETATM   40  H   UNK     0       1.734   0.782  -2.094  0.00  0.00           H+0
HETATM   41  H   UNK     0       0.963   2.109  -1.242  0.00  0.00           H+0
HETATM   42  H   UNK     0      -0.118   0.922  -1.946  0.00  0.00           H+0
HETATM   43  H   UNK     0      -1.394   3.319   1.028  0.00  0.00           H+0
HETATM   44  H   UNK     0      -4.739   3.384   2.015  0.00  0.00           H+0
HETATM   45  H   UNK     0      -4.838   3.492   0.233  0.00  0.00           H+0
HETATM   46  H   UNK     0      -3.300   5.020   0.250  0.00  0.00           H+0
HETATM   47  H   UNK     0      -5.813   0.740   1.867  0.00  0.00           H+0
HETATM   48  H   UNK     0      -0.801  -1.504   1.706  0.00  0.00           H+0
HETATM   49  H   UNK     0      -2.121  -3.079   0.789  0.00  0.00           H+0
HETATM   50  H   UNK     0      -2.463  -4.387  -2.309  0.00  0.00           H+0
HETATM   51  H   UNK     0      -2.300  -4.498  -0.541  0.00  0.00           H+0
HETATM   52  H   UNK     0      -0.804  -4.149  -1.555  0.00  0.00           H+0
HETATM   53  H   UNK     0      -3.740  -2.914  -2.436  0.00  0.00           H+0
HETATM   54  H   UNK     0      -1.819  -0.724  -2.317  0.00  0.00           H+0
HETATM   55  H   UNK     0      -1.250  -2.210  -3.093  0.00  0.00           H+0
HETATM   56  H   UNK     0       0.530  -2.581  -1.707  0.00  0.00           H+0
HETATM   57  H   UNK     0       0.652  -0.919  -2.285  0.00  0.00           H+0
HETATM   58  H   UNK     0       0.928  -1.752   0.310  0.00  0.00           H+0
CONECT    1    2   29   30   31                                             
CONECT    2    1    3    4                                                  
CONECT    3    2   32   33   34                                             
CONECT    4    2    5   35                                                  
CONECT    5    4    6   36   37                                             
CONECT    6    5    7   38   39                                             
CONECT    7    6    8    9   28                                             
CONECT    8    7   40   41   42                                             
CONECT    9    7   10                                                       
CONECT   10    9   11   19                                                  
CONECT   11   10   12   43                                                  
CONECT   12   11   13   15                                                  
CONECT   13   12   14   44   45                                             
CONECT   14   13   46                                                       
CONECT   15   12   16   18                                                  
CONECT   16   15   17   47                                                  
CONECT   17   16                                                            
CONECT   18   15   19   22                                                  
CONECT   19   18   20   10                                                  
CONECT   20   19   21   28   48                                             
CONECT   21   20   22   23   49                                             
CONECT   22   21   18                                                       
CONECT   23   21   24   25   26                                             
CONECT   24   23   50   51   52                                             
CONECT   25   23   53                                                       
CONECT   26   23   27   54   55                                             
CONECT   27   26   28   56   57                                             
CONECT   28   27    7   20   58                                             
CONECT   29    1                                                            
CONECT   30    1                                                            
CONECT   31    1                                                            
CONECT   32    3                                                            
CONECT   33    3                                                            
CONECT   34    3                                                            
CONECT   35    4                                                            
CONECT   36    5                                                            
CONECT   37    5                                                            
CONECT   38    6                                                            
CONECT   39    6                                                            
CONECT   40    8                                                            
CONECT   41    8                                                            
CONECT   42    8                                                            
CONECT   43   11                                                            
CONECT   44   13                                                            
CONECT   45   13                                                            
CONECT   46   14                                                            
CONECT   47   16                                                            
CONECT   48   20                                                            
CONECT   49   21                                                            
CONECT   50   24                                                            
CONECT   51   24                                                            
CONECT   52   24                                                            
CONECT   53   25                                                            
CONECT   54   26                                                            
CONECT   55   26                                                            
CONECT   56   27                                                            
CONECT   57   27                                                            
CONECT   58   28                                                            
MASTER        0    0    0    0    0    0    0    0   58    0  122    0
END

RDKit          3D

58 61  0  0  0  0  0  0  0  0999 V2000
    6.6660    0.8597    1.2994 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2352    0.4571    0.8965 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0594   -0.9990    0.6970 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3683    1.4050    0.7584 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9560    1.4623    0.4031 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3173    0.1376    0.2669 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8279    0.2855   -0.1497 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.8509    1.0021   -1.4589 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2489    1.1879    0.8117 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1375    1.2364    0.8393 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8936    2.3868    0.9533 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2866    2.2633    0.9653 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1230    3.4820    1.0868 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3702    4.6300    1.1758 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9026    1.0246    0.8661 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3538    0.8760    0.8766 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0667    0.8955   -0.1465 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1407   -0.1353    0.7513 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7814    0.0552    0.7459 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0513   -1.2163    0.6370 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.1317   -2.1303    0.2061 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.3529   -1.4870    0.6355 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2036   -2.4948   -1.2280 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.8964   -3.9826   -1.4451 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5221   -2.3140   -1.6716 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3148   -1.6718   -2.1236 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0830   -1.5607   -1.5866 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1506   -1.0626   -0.1677 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.2455    0.9105    0.3617 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0759    0.1039    1.9959 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6506    1.8287    1.8087 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2384   -1.4629    1.2418 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0568   -1.2126   -0.4146 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9837   -1.5472    1.0778 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7967    2.4442    0.9580 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8791    2.0682   -0.5619 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4304    2.1077    1.1700 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8479   -0.4869   -0.4507 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2544   -0.3977    1.2472 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7339    0.7816   -2.0935 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9627    2.1091   -1.2419 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1183    0.9223   -1.9464 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3937    3.3188    1.0282 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7390    3.3836    2.0147 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8382    3.4923    0.2332 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2998    5.0204    0.2496 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8134    0.7401    1.8674 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8007   -1.5035    1.7059 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1207   -3.0793    0.7887 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4627   -4.3869   -2.3090 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3002   -4.4981   -0.5407 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8039   -4.1492   -1.5549 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7404   -2.9141   -2.4363 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8185   -0.7238   -2.3175 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2505   -2.2100   -3.0934 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5300   -2.5813   -1.7069 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6515   -0.9188   -2.2853 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9281   -1.7518    0.3097 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  1
  7  8  1  0
  7  9  1  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 12 15  2  0
 15 16  1  0
 16 17  2  0
 15 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 21 23  1  0
 23 24  1  0
 23 25  1  6
 23 26  1  0
 26 27  1  0
 27 28  1  0
 28  7  1  0
 19 10  1  0
 28 20  1  0
 22 18  1  0
  1 29  1  0
  1 30  1  0
  1 31  1  0
  3 32  1  0
  3 33  1  0
  3 34  1  0
  4 35  1  0
  5 36  1  0
  5 37  1  0
  6 38  1  0
  6 39  1  0
  8 40  1  0
  8 41  1  0
  8 42  1  0
 11 43  1  0
 13 44  1  0
 13 45  1  0
 14 46  1  0
 16 47  1  0
 20 48  1  1
 21 49  1  1
 24 50  1  0
 24 51  1  0
 24 52  1  0
 25 53  1  0
 26 54  1  0
 26 55  1  0
 27 56  1  0
 27 57  1  0
 28 58  1  1
M  END

View in JSmol View NMR Assignments

Synonyms

Not Available

Chemical Formula

C₂₃H₃₀O₅

Average Mass

386.4880 Da

Monoisotopic Mass

386.20932 Da

IUPAC Name

(7S,8R,11S,12R,13S)-11-hydroxy-3-(hydroxymethyl)-7,11-dimethyl-7-(4-methylpent-3-en-1-yl)-6,15-dioxatetracyclo[10.2.1.0^{5,14}.0^{8,13}]pentadeca-1(14),2,4-triene-2-carbaldehyde

Traditional Name

(7S,8R,11S,12R,13S)-11-hydroxy-3-(hydroxymethyl)-7,11-dimethyl-7-(4-methylpent-3-en-1-yl)-6,15-dioxatetracyclo[10.2.1.0^{5,14}.0^{8,13}]pentadeca-1(14),2,4-triene-2-carbaldehyde

CAS Registry Number

Not Available

SMILES

CC(C)=CCC[C@]1(C)OC2=C3[C@H]4[C@@H](OC3=C(C=O)C(CO)=C2)[C@@](C)(O)CC[C@@H]14

InChI Identifier

InChI=1S/C23H30O5/c1-13(2)6-5-8-23(4)16-7-9-22(3,26)21-18(16)19-17(28-23)10-14(11-24)15(12-25)20(19)27-21/h6,10,12,16,18,21,24,26H,5,7-9,11H2,1-4H3/t16-,18+,21-,22+,23+/m1/s1

InChI Key

PJUNMTHNNQPMQB-MQRVUQIVSA-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
Stachybotrys	NPAtlas	11827030
Stachybotrys ruwenzoriensis RF6853	-	KNApSAcK

Chemical Taxonomy

Classification

Not classified

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	2.96	ALOGPS
logP	3.02	ChemAxon
logS	-4.5	ALOGPS
pKa (Strongest Acidic)	13.92	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	75.99 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	108.83 m³·mol⁻¹	ChemAxon
Polarizability	43.32 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

NPAtlas ID

NPA019020

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

8221268

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

10045704

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Minagawa K, Kouzuki S, Nomura K, Yamaguchi T, Kawamura Y, Matsushima K, Tani H, Ishii K, Tanimoto T, Kamigauchi T: Bisabosquals, novel squalene synthase inhibitors. I. Taxonomy, fermentation, isolation and biological activities. J Antibiot (Tokyo). 2001 Nov;54(11):890-5. doi: 10.7164/antibiotics.54.890. [PubMed:11827030 ]
Bao YR, Chen GD, Wu YH, Li XX, Hu D, Liu XZ, Li Y, Yao XS, Gao H: Stachybisbins A and B, the first cases of seco-bisabosquals from Stachybotrys bisbyi. Fitoterapia. 2015 Sep;105:151-5. doi: 10.1016/j.fitote.2015.06.022. Epub 2015 Jul 3. [PubMed:26149533 ]
Minagawa K, Kouzuki S, Nomura K, Kawamura Y, Tani H, Terui Y, Nakai H, Kamigauchi T: Bisabosquals, novel squalene synthase inhibitors. II. Physico-chemical properties and structure elucidation. J Antibiot (Tokyo). 2001 Nov;54(11):896-903. doi: 10.7164/antibiotics.54.896. [PubMed:11827031 ]

Showing NP-Card for Bisabosqual B (NP0003992)

MOL for NP0003992 (Bisabosqual B)

3D MOL for NP0003992 (Bisabosqual B)

3D SDF for NP0003992 (Bisabosqual B)

3D-SDF for NP0003992 (Bisabosqual B)

PDB for NP0003992 (Bisabosqual B)

3D PDB for NP0003992 (Bisabosqual B)

SMILES for NP0003992 (Bisabosqual B)

INCHI for NP0003992 (Bisabosqual B)

Structure for NP0003992 (Bisabosqual B)

3D Structure for NP0003992 (Bisabosqual B)