NP-MRD: Showing NP-Card for (2r,2'r,4'as,6'r,8'as)-4,6'-dihydroxy-2',5',5',8'a-tetramethyl-3',4',4'a,6',7',8'-hexahydro-2'h,3h-spiro[1-benzofuran-2,1'-naphthalene]-6,7-dicarbaldehyde (NP0271246)

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Record Information

Version

2.0

Created at

2022-09-08 17:28:29 UTC

Updated at

2022-09-08 17:28:29 UTC

NP-MRD ID

NP0271246

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(2r,2'r,4'as,6'r,8'as)-4,6'-dihydroxy-2',5',5',8'a-tetramethyl-3',4',4'a,6',7',8'-hexahydro-2'h,3h-spiro[1-benzofuran-2,1'-naphthalene]-6,7-dicarbaldehyde

Description

Stachybotrydial, also known as mer NF5003F, belongs to the class of organic compounds known as benzofurans. These are organic compounds containing a benzene ring fused to a furan. Furan is a five-membered aromatic ring with four carbon atoms and one oxygen atom. (2r,2'r,4'as,6'r,8'as)-4,6'-dihydroxy-2',5',5',8'a-tetramethyl-3',4',4'a,6',7',8'-hexahydro-2'h,3h-spiro[1-benzofuran-2,1'-naphthalene]-6,7-dicarbaldehyde is found in Stachybotrys cylindrospora and Stachybotrys nephrospora. (2r,2'r,4'as,6'r,8'as)-4,6'-dihydroxy-2',5',5',8'a-tetramethyl-3',4',4'a,6',7',8'-hexahydro-2'h,3h-spiro[1-benzofuran-2,1'-naphthalene]-6,7-dicarbaldehyde was first documented in 2004 (PMID: 15549667). Based on a literature review a small amount of articles have been published on Stachybotrydial (PMID: 34361605) (PMID: 25087962) (PMID: 18057696) (PMID: 15882970).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309082219282D          

 28 31  0  0  1  0            999 V2000
    1.8349    2.5857    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5266    2.1359    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.2619    2.5100    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9535    2.0602    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9098    1.2363    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.6014    0.7866    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4051    0.6004    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9242    1.5458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5577   -0.0373    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.2493   -0.4871    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8223   -0.4113    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1307    0.0384    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1744    0.8623    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.5907    0.2793    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4828    1.3121    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.3532    0.4973    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5383    0.3688    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0885   -0.3228    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4626   -1.0582    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2647   -0.2791    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1094    0.4562    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9332    0.4999    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3830   -0.1917    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3404    1.1478    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0336    1.8832    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8575    1.9269    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1643    1.1041    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7480    1.6871    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  6  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  5  4  1  1  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  6  8  1  0  0  0  0
  6  9  1  0  0  0  0
  9 10  1  6  0  0  0
  9 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
  5 13  1  0  0  0  0
 13 14  1  1  0  0  0
 13 15  1  0  0  0  0
  2 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
 18 20  1  0  0  0  0
 20 21  2  0  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 21 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  2  0  0  0  0
 24 27  2  0  0  0  0
 17 27  1  0  0  0  0
 27 28  1  0  0  0  0
 15 28  1  6  0  0  0
M  END

     RDKit          3D

 58 61  0  0  0  0  0  0  0  0999 V2000
   -0.0658   -2.0179   -2.2740 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0338   -2.2579   -0.7666 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.3171   -2.7935   -0.2463 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1918   -1.8021    0.4438 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8881   -0.4544   -0.1275 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.9953    0.5167    0.1069 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1430    0.0475   -0.8120 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5499    0.5106    1.5018 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6557    1.8930   -0.3845 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.8020    1.9239   -1.7758 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2781    2.3493   -0.0587 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2516    1.3119   -0.3602 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5345   -0.0278    0.3154 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.4780    0.2683    1.8101 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4840   -1.0355   -0.0697 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4234   -1.4539    1.0038 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6411   -0.6095    0.8550 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7267   -0.3649    1.6979 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7899   -0.9793    2.9529 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7063    0.4862    1.2488 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6319    1.0887    0.0028 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7029    1.9834   -0.4195 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6775    2.5512   -1.5396 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5519    0.8368   -0.8192 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4295    1.4452   -2.1341 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8407    2.5485   -2.2235 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5391   -0.0275   -0.3848 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3930   -0.4262   -1.0049 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0480   -2.3259   -2.7132 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1777   -0.9493   -2.5176 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6952   -2.6140   -2.8188 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7232   -3.0887   -0.6248 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1854   -3.6639    0.4485 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8801   -3.2251   -1.1212 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2662   -2.0747    0.2313 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0262   -1.8793    1.5400 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8243   -0.5939   -1.2475 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7639   -0.2347   -1.7992 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8326    0.9358   -0.8705 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7285   -0.7484   -0.3102 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0984   -0.2601    2.1598 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6583    0.2898    1.5328 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4827    1.5333    1.9784 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3744    2.6380    0.0290 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6417    2.3602   -2.0617 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0540    3.2105   -0.7600 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1854    2.8029    0.9527 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7567    1.6369   -0.0361 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2032    1.2027   -1.4711 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5764    0.6327    1.9919 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1250    1.1060    2.0763 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7390   -0.5811    2.4356 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7800   -2.5148    0.8513 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0842   -1.3820    2.0223 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0395   -1.5974    3.2319 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5670    0.6985    1.8816 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5455    2.1790    0.2235 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8183    0.9961   -3.0309 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  6  8  1  0
  6  9  1  0
  9 10  1  0
  9 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  1
 13 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 18 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  2  0
 21 24  1  0
 24 25  1  0
 25 26  2  0
 24 27  2  0
 27 28  1  0
 15  2  1  0
 15 28  1  6
 13  5  1  0
 27 17  1  0
  1 29  1  0
  1 30  1  0
  1 31  1  0
  2 32  1  6
  3 33  1  0
  3 34  1  0
  4 35  1  0
  4 36  1  0
  5 37  1  6
  7 38  1  0
  7 39  1  0
  7 40  1  0
  8 41  1  0
  8 42  1  0
  8 43  1  0
  9 44  1  1
 10 45  1  0
 11 46  1  0
 11 47  1  0
 12 48  1  0
 12 49  1  0
 14 50  1  0
 14 51  1  0
 14 52  1  0
 16 53  1  0
 16 54  1  0
 19 55  1  0
 20 56  1  0
 22 57  1  0
 25 58  1  0
M  END


  Mrv1652309082219282D          

 28 31  0  0  1  0            999 V2000
    1.8349    2.5857    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5266    2.1359    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.2619    2.5100    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9535    2.0602    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9098    1.2363    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.6014    0.7866    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4051    0.6004    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9242    1.5458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5577   -0.0373    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.2493   -0.4871    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8223   -0.4113    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1307    0.0384    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1744    0.8623    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.5907    0.2793    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4828    1.3121    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.3532    0.4973    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5383    0.3688    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0885   -0.3228    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4626   -1.0582    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2647   -0.2791    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1094    0.4562    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9332    0.4999    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3830   -0.1917    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3404    1.1478    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0336    1.8832    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8575    1.9269    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1643    1.1041    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7480    1.6871    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  6  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  5  4  1  1  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  6  8  1  0  0  0  0
  6  9  1  0  0  0  0
  9 10  1  6  0  0  0
  9 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
  5 13  1  0  0  0  0
 13 14  1  1  0  0  0
 13 15  1  0  0  0  0
  2 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
 18 20  1  0  0  0  0
 20 21  2  0  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 21 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  2  0  0  0  0
 24 27  2  0  0  0  0
 17 27  1  0  0  0  0
 27 28  1  0  0  0  0
 15 28  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0271246

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@@H]1CC[C@H]2C(C)(C)[C@H](O)CC[C@]2(C)[C@@]11CC2=C(O)C=C(C=O)C(C=O)=C2O1

> <INCHI_IDENTIFIER>
InChI=1S/C23H30O5/c1-13-5-6-18-21(2,3)19(27)7-8-22(18,4)23(13)10-15-17(26)9-14(11-24)16(12-25)20(15)28-23/h9,11-13,18-19,26-27H,5-8,10H2,1-4H3/t13-,18+,19-,22+,23-/m1/s1

> <INCHI_KEY>
WIGGVNIABVHHCS-QJAXDWLUSA-N

> <FORMULA>
C23H30O5

> <MOLECULAR_WEIGHT>
386.488

> <EXACT_MASS>
386.209324066

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
58

> <JCHEM_AVERAGE_POLARIZABILITY>
42.02021017817607

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2R,2'R,4'aS,6'R,8'aS)-4,6'-dihydroxy-2',5',5',8'a-tetramethyl-3',4',4'a,5',6',7',8',8'a-octahydro-2'H,3H-spiro[1-benzofuran-2,1'-naphthalene]-6,7-dicarbaldehyde

> <JCHEM_LOGP>
3.8765738453333327

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
19.489318124923358

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.124681492302317

> <JCHEM_PKA_STRONGEST_BASIC>
-0.8351379938481479

> <JCHEM_POLAR_SURFACE_AREA>
83.83

> <JCHEM_REFRACTIVITY>
107.71239999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(2R,2'R,4'aS,6'R,8'aS)-4,6'-dihydroxy-2',5',5',8'a-tetramethyl-3',4',4'a,6',7',8'-hexahydro-2'H,3H-spiro[1-benzofuran-2,1'-naphthalene]-6,7-dicarbaldehyde

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 08-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   08-SEP-22         0                                  
HETATM    1  C   UNK     0       3.425   4.827   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       4.716   3.987   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       6.089   4.685   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       7.380   3.846   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       7.298   2.308   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       8.589   1.468   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      10.090   1.121   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       9.192   2.885   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       8.508  -0.070   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       9.799  -0.909   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       7.135  -0.768   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       5.844   0.072   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       5.926   1.610   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.836   0.521   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.635   2.449   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       4.393   0.928   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       2.872   0.688   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       2.032  -0.603   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       2.730  -1.975   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       0.494  -0.521   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -0.204   0.852   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -1.742   0.933   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0      -2.582  -0.358   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0       0.635   2.143   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      -0.063   3.515   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0      -1.601   3.597   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0       2.173   2.061   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0       3.263   3.149   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   15                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6   13                                                  
CONECT    6    5    7    8    9                                             
CONECT    7    6                                                            
CONECT    8    6                                                            
CONECT    9    6   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12    5   14   15                                             
CONECT   14   13                                                            
CONECT   15   13    2   16   28                                             
CONECT   16   15   17                                                       
CONECT   17   16   18   27                                                  
CONECT   18   17   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18   21                                                       
CONECT   21   20   22   24                                                  
CONECT   22   21   23                                                       
CONECT   23   22                                                            
CONECT   24   21   25   27                                                  
CONECT   25   24   26                                                       
CONECT   26   25                                                            
CONECT   27   24   17   28                                                  
CONECT   28   27   15                                                       
MASTER        0    0    0    0    0    0    0    0   28    0   62    0
END

View in JSmol

Synonyms

Value	Source
Mer NF5003F	MeSH
ATCC 20928 factor a	MeSH
Mer-NF5003F	MeSH

Chemical Formula

C₂₃H₃₀O₅

Average Mass

386.4880 Da

Monoisotopic Mass

386.20932 Da

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

C[C@@H]1CC[C@H]2C(C)(C)[C@H](O)CC[C@]2(C)[C@@]11CC2=C(O)C=C(C=O)C(C=O)=C2O1

InChI Identifier

InChI=1S/C23H30O5/c1-13-5-6-18-21(2,3)19(27)7-8-22(18,4)23(13)10-15-17(26)9-14(11-24)16(12-25)20(15)28-23/h9,11-13,18-19,26-27H,5-8,10H2,1-4H3/t13-,18+,19-,22+,23-/m1/s1

InChI Key

WIGGVNIABVHHCS-QJAXDWLUSA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Stachybotrys cylindrospora	LOTUS Database	35616633
Stachybotrys nephrospora	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as benzofurans. These are organic compounds containing a benzene ring fused to a furan. Furan is a five-membered aromatic ring with four carbon atoms and one oxygen atom.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Benzofurans

Sub Class

Not Available

Direct Parent

Benzofurans

Alternative Parents

Substituents

Benzofuran
Coumaran
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
Aryl-aldehyde
Benzenoid
Cyclic alcohol
Secondary alcohol
Ether
Oxacycle
Alcohol
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Aldehyde
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

8062157

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

9886484

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Haidar S, Jurgens FM, Aichele D, Jagels A, Humpf HU, Jose J: Natural Compounds Isolated from Stachybotrys chartarum Are Potent Inhibitors of Human Protein Kinase CK2. Molecules. 2021 Jul 23;26(15):4453. doi: 10.3390/molecules26154453. [PubMed:34361605 ]
Kwon YJ, Sohn MJ, Kim HJ, Kim WG: The Lactone form of stachybotrydial: a new inhibitor of dihydrofolate reductase from stachybotrys sp. FN298. Biol Pharm Bull. 2014;37(8):1406-10. doi: 10.1248/bpb.b14-00108. [PubMed:25087962 ]
Sasaoka M, Wada Y, Hasumi K: Stachybotrydial selectively enhances fibrin binding and activation of Glu-plasminogen. J Antibiot (Tokyo). 2007 Nov;60(11):674-81. doi: 10.1038/ja.2007.86. [PubMed:18057696 ]
Lin TW, Chang WW, Chen CC, Tsai YC: Stachybotrydial, a potent inhibitor of fucosyltransferase and sialyltransferase. Biochem Biophys Res Commun. 2005 Jun 17;331(4):953-7. doi: 10.1016/j.bbrc.2005.03.232. [PubMed:15882970 ]
Sawadjoon S, Kittakoop P, Isaka M, Kirtikara K, Madla S, Thebtaranonth Y: Antiviral and antiplasmodial spirodihydrobenzofuran terpenes from the fungus Stachybotrys nephrospora. Planta Med. 2004 Nov;70(11):1085-7. doi: 10.1055/s-2004-832652. [PubMed:15549667 ]
LOTUS database [Link]

Showing NP-Card for (2r,2'r,4'as,6'r,8'as)-4,6'-dihydroxy-2',5',5',8'a-tetramethyl-3',4',4'a,6',7',8'-hexahydro-2'h,3h-spiro[1-benzofuran-2,1'-naphthalene]-6,7-dicarbaldehyde (NP0271246)

MOL for NP0271246 ((2r,2'r,4'as,6'r,8'as)-4,6'-dihydroxy-2',5',5',8'a-tetramethyl-3',4',4'a,6',7',8'-hexahydro-2'h,3h-spiro[1-benzofuran-2,1'-naphthalene]-6,7-dicarbaldehyde)

3D MOL for NP0271246 ((2r,2'r,4'as,6'r,8'as)-4,6'-dihydroxy-2',5',5',8'a-tetramethyl-3',4',4'a,6',7',8'-hexahydro-2'h,3h-spiro[1-benzofuran-2,1'-naphthalene]-6,7-dicarbaldehyde)

3D SDF for NP0271246 ((2r,2'r,4'as,6'r,8'as)-4,6'-dihydroxy-2',5',5',8'a-tetramethyl-3',4',4'a,6',7',8'-hexahydro-2'h,3h-spiro[1-benzofuran-2,1'-naphthalene]-6,7-dicarbaldehyde)

3D-SDF for NP0271246 ((2r,2'r,4'as,6'r,8'as)-4,6'-dihydroxy-2',5',5',8'a-tetramethyl-3',4',4'a,6',7',8'-hexahydro-2'h,3h-spiro[1-benzofuran-2,1'-naphthalene]-6,7-dicarbaldehyde)

PDB for NP0271246 ((2r,2'r,4'as,6'r,8'as)-4,6'-dihydroxy-2',5',5',8'a-tetramethyl-3',4',4'a,6',7',8'-hexahydro-2'h,3h-spiro[1-benzofuran-2,1'-naphthalene]-6,7-dicarbaldehyde)

3D PDB for NP0271246 ((2r,2'r,4'as,6'r,8'as)-4,6'-dihydroxy-2',5',5',8'a-tetramethyl-3',4',4'a,6',7',8'-hexahydro-2'h,3h-spiro[1-benzofuran-2,1'-naphthalene]-6,7-dicarbaldehyde)

SMILES for NP0271246 ((2r,2'r,4'as,6'r,8'as)-4,6'-dihydroxy-2',5',5',8'a-tetramethyl-3',4',4'a,6',7',8'-hexahydro-2'h,3h-spiro[1-benzofuran-2,1'-naphthalene]-6,7-dicarbaldehyde)

INCHI for NP0271246 ((2r,2'r,4'as,6'r,8'as)-4,6'-dihydroxy-2',5',5',8'a-tetramethyl-3',4',4'a,6',7',8'-hexahydro-2'h,3h-spiro[1-benzofuran-2,1'-naphthalene]-6,7-dicarbaldehyde)

Structure for NP0271246 ((2r,2'r,4'as,6'r,8'as)-4,6'-dihydroxy-2',5',5',8'a-tetramethyl-3',4',4'a,6',7',8'-hexahydro-2'h,3h-spiro[1-benzofuran-2,1'-naphthalene]-6,7-dicarbaldehyde)

3D Structure for NP0271246 ((2r,2'r,4'as,6'r,8'as)-4,6'-dihydroxy-2',5',5',8'a-tetramethyl-3',4',4'a,6',7',8'-hexahydro-2'h,3h-spiro[1-benzofuran-2,1'-naphthalene]-6,7-dicarbaldehyde)