NP-MRD: Showing NP-Card for Spirobenzofuran (NP0003821)

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Record Information

Version

2.0

Created at

2020-12-09 00:57:48 UTC

Updated at

2021-07-15 16:47:28 UTC

NP-MRD ID

NP0003821

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Spirobenzofuran

Provided By

NPAtlas

Description

2,5-Dihydroxy-2',2',6-trimethyl-2H-spiro[1-benzofuran-3,1'-cyclopentane]-4'-one 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. Spirobenzofuran is found in Acremonium. Spirobenzofuran was first documented in 2001 (PMID: 11513045). Based on a literature review very few articles have been published on 2,5-dihydroxy-2',2',6-trimethyl-2H-spiro[1-benzofuran-3,1'-cyclopentane]-4'-one (PMID: 29773898) (PMID: 32573247) (PMID: 31813853) (PMID: 28398053).

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306242117503D          

 37 39  0  0  0  0            999 V2000
    4.4859    1.2373   -0.0230 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1020    0.6908   -0.0398 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3101    0.8299   -1.1604 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0111    0.3368   -1.2251 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5227   -0.3119   -0.1101 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3135   -0.4532    1.0148 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5970    0.0428    1.0570 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3270   -0.1392    2.2223 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8695   -0.7249   -0.4632 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.2909   -1.9854    0.1918 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.2135   -1.6009    1.3176 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8945   -2.3477    1.9849 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1167   -0.1471    1.4366 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.7943    0.3381    0.0161 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.0968    1.6762    0.1930 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0564    0.4761   -0.7591 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7543   -0.8155   -1.9599 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.9297   -0.8604   -2.6297 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0269    0.3530   -2.2326 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6350    1.8605   -0.9382 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2121    0.4036   -0.0942 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6625    1.8507    0.8727 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7190    1.3455   -2.0262 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8582   -0.9792    1.8606 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9440   -0.6187    3.0248 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4983   -2.6522    0.5197 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9353   -2.5654   -0.5236 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2780    0.1065    2.1086 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0190    0.3656    1.7729 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1281    1.5208    0.6978 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9648    2.1962   -0.7772 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7446    2.2783    0.8612 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7795    1.0676   -0.1531 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8991    1.0481   -1.6906 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4915   -0.5244   -0.9232 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0765   -1.6748   -2.1790 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8956   -1.6230   -3.2845 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  5  9  1  0  0  0  0
  9 10  1  1  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 11 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  1  0  0  0
 14 16  1  0  0  0  0
  9 17  1  0  0  0  0
 17 18  1  0  0  0  0
 17 19  1  0  0  0  0
  7  2  1  0  0  0  0
 14  9  1  0  0  0  0
 19  4  1  0  0  0  0
  1 20  1  0  0  0  0
  1 21  1  0  0  0  0
  1 22  1  0  0  0  0
  3 23  1  0  0  0  0
  6 24  1  0  0  0  0
  8 25  1  0  0  0  0
 10 26  1  0  0  0  0
 10 27  1  0  0  0  0
 13 28  1  0  0  0  0
 13 29  1  0  0  0  0
 15 30  1  0  0  0  0
 15 31  1  0  0  0  0
 15 32  1  0  0  0  0
 16 33  1  0  0  0  0
 16 34  1  0  0  0  0
 16 35  1  0  0  0  0
 17 36  1  1  0  0  0
 18 37  1  0  0  0  0
M  END

     RDKit          3D

 37 39  0  0  0  0  0  0  0  0999 V2000
    4.4859    1.2373   -0.0230 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1020    0.6908   -0.0398 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3101    0.8299   -1.1604 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0111    0.3368   -1.2251 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5227   -0.3119   -0.1101 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3135   -0.4532    1.0148 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5970    0.0428    1.0570 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3270   -0.1392    2.2223 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8695   -0.7249   -0.4632 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.2909   -1.9854    0.1918 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2135   -1.6009    1.3176 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8945   -2.3477    1.9849 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1167   -0.1471    1.4366 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7943    0.3381    0.0161 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.0968    1.6762    0.1930 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0564    0.4761   -0.7591 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7543   -0.8155   -1.9599 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.9297   -0.8604   -2.6297 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0269    0.3530   -2.2326 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6350    1.8605   -0.9382 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2121    0.4036   -0.0942 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6625    1.8507    0.8727 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7190    1.3455   -2.0262 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8582   -0.9792    1.8606 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9440   -0.6187    3.0248 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4983   -2.6522    0.5197 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9353   -2.5654   -0.5236 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2780    0.1065    2.1086 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0190    0.3656    1.7729 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1281    1.5208    0.6978 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9648    2.1962   -0.7772 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7446    2.2783    0.8612 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7795    1.0676   -0.1531 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8991    1.0481   -1.6906 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4915   -0.5244   -0.9232 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0765   -1.6748   -2.1790 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8956   -1.6230   -3.2845 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  5  9  1  0
  9 10  1  1
 10 11  1  0
 11 12  2  0
 11 13  1  0
 13 14  1  0
 14 15  1  1
 14 16  1  0
  9 17  1  0
 17 18  1  0
 17 19  1  0
  7  2  1  0
 14  9  1  0
 19  4  1  0
  1 20  1  0
  1 21  1  0
  1 22  1  0
  3 23  1  0
  6 24  1  0
  8 25  1  0
 10 26  1  0
 10 27  1  0
 13 28  1  0
 13 29  1  0
 15 30  1  0
 15 31  1  0
 15 32  1  0
 16 33  1  0
 16 34  1  0
 16 35  1  0
 17 36  1  1
 18 37  1  0
M  END


  Mrv1652306242117503D          

 37 39  0  0  0  0            999 V2000
    4.4859    1.2373   -0.0230 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1020    0.6908   -0.0398 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3101    0.8299   -1.1604 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0111    0.3368   -1.2251 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5227   -0.3119   -0.1101 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3135   -0.4532    1.0148 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5970    0.0428    1.0570 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3270   -0.1392    2.2223 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8695   -0.7249   -0.4632 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.2909   -1.9854    0.1918 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.2135   -1.6009    1.3176 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8945   -2.3477    1.9849 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1167   -0.1471    1.4366 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.7943    0.3381    0.0161 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.0968    1.6762    0.1930 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0564    0.4761   -0.7591 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7543   -0.8155   -1.9599 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.9297   -0.8604   -2.6297 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0269    0.3530   -2.2326 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6350    1.8605   -0.9382 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2121    0.4036   -0.0942 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6625    1.8507    0.8727 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7190    1.3455   -2.0262 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8582   -0.9792    1.8606 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9440   -0.6187    3.0248 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4983   -2.6522    0.5197 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9353   -2.5654   -0.5236 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2780    0.1065    2.1086 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0190    0.3656    1.7729 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1281    1.5208    0.6978 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9648    2.1962   -0.7772 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7446    2.2783    0.8612 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7795    1.0676   -0.1531 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8991    1.0481   -1.6906 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4915   -0.5244   -0.9232 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0765   -1.6748   -2.1790 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8956   -1.6230   -3.2845 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  5  9  1  0  0  0  0
  9 10  1  1  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 11 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  1  0  0  0
 14 16  1  0  0  0  0
  9 17  1  0  0  0  0
 17 18  1  0  0  0  0
 17 19  1  0  0  0  0
  7  2  1  0  0  0  0
 14  9  1  0  0  0  0
 19  4  1  0  0  0  0
  1 20  1  0  0  0  0
  1 21  1  0  0  0  0
  1 22  1  0  0  0  0
  3 23  1  0  0  0  0
  6 24  1  0  0  0  0
  8 25  1  0  0  0  0
 10 26  1  0  0  0  0
 10 27  1  0  0  0  0
 13 28  1  0  0  0  0
 13 29  1  0  0  0  0
 15 30  1  0  0  0  0
 15 31  1  0  0  0  0
 15 32  1  0  0  0  0
 16 33  1  0  0  0  0
 16 34  1  0  0  0  0
 16 35  1  0  0  0  0
 17 36  1  1  0  0  0
 18 37  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0003821

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC1=C([H])C2=C(O[C@]([H])(O[H])[C@@]22C([H])([H])C(=O)C([H])([H])C2(C([H])([H])[H])C([H])([H])[H])C([H])=C1C([H])([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C15H18O4/c1-8-4-12-10(5-11(8)17)15(13(18)19-12)7-9(16)6-14(15,2)3/h4-5,13,17-18H,6-7H2,1-3H3/t13-,15+/m0/s1

> <INCHI_KEY>
GASOCDUVJSYZGK-UHFFFAOYSA-N

> <FORMULA>
C15H18O4

> <MOLECULAR_WEIGHT>
262.305

> <EXACT_MASS>
262.12050906

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
37

> <JCHEM_AVERAGE_POLARIZABILITY>
27.541381881372125

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2S,3R)-2,5-dihydroxy-2',2',6-trimethyl-2H-spiro[1-benzofuran-3,1'-cyclopentane]-4'-one

> <ALOGPS_LOGP>
1.82

> <JCHEM_LOGP>
2.2773287773333335

> <ALOGPS_LOGS>
-2.19

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
11.703482800335339

> <JCHEM_PKA_STRONGEST_ACIDIC>
10.082207488286356

> <JCHEM_PKA_STRONGEST_BASIC>
-4.274636148156859

> <JCHEM_POLAR_SURFACE_AREA>
66.76

> <JCHEM_REFRACTIVITY>
69.81739999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.69e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2S,3R)-2,5-dihydroxy-2',2',6-trimethyl-2H-spiro[1-benzofuran-3,1'-cyclopentane]-4'-one

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 37 39  0  0  0  0  0  0  0  0999 V2000
    4.4859    1.2373   -0.0230 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1020    0.6908   -0.0398 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3101    0.8299   -1.1604 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0111    0.3368   -1.2251 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5227   -0.3119   -0.1101 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3135   -0.4532    1.0148 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5970    0.0428    1.0570 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3270   -0.1392    2.2223 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8695   -0.7249   -0.4632 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.2909   -1.9854    0.1918 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2135   -1.6009    1.3176 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8945   -2.3477    1.9849 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1167   -0.1471    1.4366 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7943    0.3381    0.0161 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.0968    1.6762    0.1930 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0564    0.4761   -0.7591 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7543   -0.8155   -1.9599 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.9297   -0.8604   -2.6297 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0269    0.3530   -2.2326 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6350    1.8605   -0.9382 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2121    0.4036   -0.0942 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6625    1.8507    0.8727 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7190    1.3455   -2.0262 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8582   -0.9792    1.8606 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9440   -0.6187    3.0248 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4983   -2.6522    0.5197 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9353   -2.5654   -0.5236 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2780    0.1065    2.1086 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0190    0.3656    1.7729 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1281    1.5208    0.6978 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9648    2.1962   -0.7772 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7446    2.2783    0.8612 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7795    1.0676   -0.1531 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8991    1.0481   -1.6906 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4915   -0.5244   -0.9232 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0765   -1.6748   -2.1790 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8956   -1.6230   -3.2845 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  5  9  1  0
  9 10  1  1
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  9 17  1  0
 17 18  1  0
 17 19  1  0
  7  2  1  0
 14  9  1  0
 19  4  1  0
  1 20  1  0
  1 21  1  0
  1 22  1  0
  3 23  1  0
  6 24  1  0
  8 25  1  0
 10 26  1  0
 10 27  1  0
 13 28  1  0
 13 29  1  0
 15 30  1  0
 15 31  1  0
 15 32  1  0
 16 33  1  0
 16 34  1  0
 16 35  1  0
 17 36  1  1
 18 37  1  0
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       4.486   1.237  -0.023  0.00  0.00           C+0
HETATM    2  C   UNK     0       3.102   0.691  -0.040  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.310   0.830  -1.160  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.011   0.337  -1.225  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.523  -0.312  -0.110  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.313  -0.453   1.015  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.597   0.043   1.057  0.00  0.00           C+0
HETATM    8  O   UNK     0       3.327  -0.139   2.222  0.00  0.00           O+0
HETATM    9  C   UNK     0      -0.870  -0.725  -0.463  0.00  0.00           C+0
HETATM   10  C   UNK     0      -1.291  -1.985   0.192  0.00  0.00           C+0
HETATM   11  C   UNK     0      -2.213  -1.601   1.318  0.00  0.00           C+0
HETATM   12  O   UNK     0      -2.894  -2.348   1.985  0.00  0.00           O+0
HETATM   13  C   UNK     0      -2.117  -0.147   1.437  0.00  0.00           C+0
HETATM   14  C   UNK     0      -1.794   0.338   0.016  0.00  0.00           C+0
HETATM   15  C   UNK     0      -1.097   1.676   0.193  0.00  0.00           C+0
HETATM   16  C   UNK     0      -3.056   0.476  -0.759  0.00  0.00           C+0
HETATM   17  C   UNK     0      -0.754  -0.816  -1.960  0.00  0.00           C+0
HETATM   18  O   UNK     0      -1.930  -0.860  -2.630  0.00  0.00           O+0
HETATM   19  O   UNK     0       0.027   0.353  -2.233  0.00  0.00           O+0
HETATM   20  H   UNK     0       4.635   1.861  -0.938  0.00  0.00           H+0
HETATM   21  H   UNK     0       5.212   0.404  -0.094  0.00  0.00           H+0
HETATM   22  H   UNK     0       4.662   1.851   0.873  0.00  0.00           H+0
HETATM   23  H   UNK     0       2.719   1.345  -2.026  0.00  0.00           H+0
HETATM   24  H   UNK     0       0.858  -0.979   1.861  0.00  0.00           H+0
HETATM   25  H   UNK     0       2.944  -0.619   3.025  0.00  0.00           H+0
HETATM   26  H   UNK     0      -0.498  -2.652   0.520  0.00  0.00           H+0
HETATM   27  H   UNK     0      -1.935  -2.565  -0.524  0.00  0.00           H+0
HETATM   28  H   UNK     0      -1.278   0.107   2.109  0.00  0.00           H+0
HETATM   29  H   UNK     0      -3.019   0.366   1.773  0.00  0.00           H+0
HETATM   30  H   UNK     0      -0.128   1.521   0.698  0.00  0.00           H+0
HETATM   31  H   UNK     0      -0.965   2.196  -0.777  0.00  0.00           H+0
HETATM   32  H   UNK     0      -1.745   2.278   0.861  0.00  0.00           H+0
HETATM   33  H   UNK     0      -3.780   1.068  -0.153  0.00  0.00           H+0
HETATM   34  H   UNK     0      -2.899   1.048  -1.691  0.00  0.00           H+0
HETATM   35  H   UNK     0      -3.491  -0.524  -0.923  0.00  0.00           H+0
HETATM   36  H   UNK     0      -0.077  -1.675  -2.179  0.00  0.00           H+0
HETATM   37  H   UNK     0      -1.896  -1.623  -3.285  0.00  0.00           H+0
CONECT    1    2   20   21   22                                             
CONECT    2    1    3    7                                                  
CONECT    3    2    4   23                                                  
CONECT    4    3    5   19                                                  
CONECT    5    4    6    9                                                  
CONECT    6    5    7   24                                                  
CONECT    7    6    8    2                                                  
CONECT    8    7   25                                                       
CONECT    9    5   10   17   14                                             
CONECT   10    9   11   26   27                                             
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14   28   29                                             
CONECT   14   13   15   16    9                                             
CONECT   15   14   30   31   32                                             
CONECT   16   14   33   34   35                                             
CONECT   17    9   18   19   36                                             
CONECT   18   17   37                                                       
CONECT   19   17    4                                                       
CONECT   20    1                                                            
CONECT   21    1                                                            
CONECT   22    1                                                            
CONECT   23    3                                                            
CONECT   24    6                                                            
CONECT   25    8                                                            
CONECT   26   10                                                            
CONECT   27   10                                                            
CONECT   28   13                                                            
CONECT   29   13                                                            
CONECT   30   15                                                            
CONECT   31   15                                                            
CONECT   32   15                                                            
CONECT   33   16                                                            
CONECT   34   16                                                            
CONECT   35   16                                                            
CONECT   36   17                                                            
CONECT   37   18                                                            
MASTER        0    0    0    0    0    0    0    0   37    0   78    0
END

RDKit          3D

37 39  0  0  0  0  0  0  0  0999 V2000
    4.4859    1.2373   -0.0230 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1020    0.6908   -0.0398 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3101    0.8299   -1.1604 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0111    0.3368   -1.2251 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5227   -0.3119   -0.1101 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3135   -0.4532    1.0148 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5970    0.0428    1.0570 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3270   -0.1392    2.2223 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8695   -0.7249   -0.4632 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.2909   -1.9854    0.1918 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2135   -1.6009    1.3176 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8945   -2.3477    1.9849 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1167   -0.1471    1.4366 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7943    0.3381    0.0161 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.0968    1.6762    0.1930 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0564    0.4761   -0.7591 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7543   -0.8155   -1.9599 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.9297   -0.8604   -2.6297 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0269    0.3530   -2.2326 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6350    1.8605   -0.9382 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2121    0.4036   -0.0942 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6625    1.8507    0.8727 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7190    1.3455   -2.0262 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8582   -0.9792    1.8606 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9440   -0.6187    3.0248 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4983   -2.6522    0.5197 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9353   -2.5654   -0.5236 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2780    0.1065    2.1086 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0190    0.3656    1.7729 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1281    1.5208    0.6978 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9648    2.1962   -0.7772 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7446    2.2783    0.8612 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7795    1.0676   -0.1531 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8991    1.0481   -1.6906 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4915   -0.5244   -0.9232 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0765   -1.6748   -2.1790 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8956   -1.6230   -3.2845 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  5  9  1  0
  9 10  1  1
 10 11  1  0
 11 12  2  0
 11 13  1  0
 13 14  1  0
 14 15  1  1
 14 16  1  0
  9 17  1  0
 17 18  1  0
 17 19  1  0
  7  2  1  0
 14  9  1  0
 19  4  1  0
  1 20  1  0
  1 21  1  0
  1 22  1  0
  3 23  1  0
  6 24  1  0
  8 25  1  0
 10 26  1  0
 10 27  1  0
 13 28  1  0
 13 29  1  0
 15 30  1  0
 15 31  1  0
 15 32  1  0
 16 33  1  0
 16 34  1  0
 16 35  1  0
 17 36  1  1
 18 37  1  0
M  END

View in JSmol View NMR Assignments

Synonyms

Not Available

Chemical Formula

C₁₅H₁₈O₄

Average Mass

262.3050 Da

Monoisotopic Mass

262.12051 Da

IUPAC Name

(2S,3R)-2,5-dihydroxy-2',2',6-trimethyl-2H-spiro[1-benzofuran-3,1'-cyclopentane]-4'-one

Traditional Name

(2S,3R)-2,5-dihydroxy-2',2',6-trimethyl-2H-spiro[1-benzofuran-3,1'-cyclopentane]-4'-one

CAS Registry Number

Not Available

SMILES

CC1=C(O)C=C2C(OC(O)C22CC(=O)CC2(C)C)=C1

InChI Identifier

InChI=1S/C15H18O4/c1-8-4-12-10(5-11(8)17)15(13(18)19-12)7-9(16)6-14(15,2)3/h4-5,13,17-18H,6-7H2,1-3H3

InChI Key

GASOCDUVJSYZGK-UHFFFAOYSA-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
Acremonium	NPAtlas	11513045

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

Coumaran
Benzofuran
1-hydroxy-2-unsubstituted benzenoid
Phenol
Benzenoid
Cyclic ketone
Ketone
Hemiacetal
Oxacycle
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
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
logP	1.82	ALOGPS
logP	2.28	ChemAxon
logS	-2.2	ALOGPS
pKa (Strongest Acidic)	10.08	ChemAxon
pKa (Strongest Basic)	-4.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	66.76 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	69.82 m³·mol⁻¹	ChemAxon
Polarizability	27.54 Å³	ChemAxon
Number of Rings	3	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

NPA013423

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

8236795

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

10061243

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Kleinwachter P, Schlegel B, Dorfelt H, Grafe U: Spirobenzofuran, a new bioactive metabolite from Acremonium sp.HKI 0230. J Antibiot (Tokyo). 2001 Jun;54(6):526-7. doi: 10.7164/antibiotics.54.526. [PubMed:11513045 ]
Kim JY, Woo EE, Lee IK, Yun BS: New antioxidants from the culture broth of Hericium coralloides. J Antibiot (Tokyo). 2018 Sep;71(9):822-825. doi: 10.1038/s41429-018-0067-6. Epub 2018 May 17. [PubMed:29773898 ]
Fang QY, Yi MH, Wu XX, Zhao LM: Regio- and Diastereoselective Spirocyclopropanation of Benzofuran-Derived Azadienes through 1,4-Addition-Induced Dearomatization Reaction under Mild Conditions. Org Lett. 2020 Jul 2;22(13):5266-5270. doi: 10.1021/acs.orglett.0c01987. Epub 2020 Jun 23. [PubMed:32573247 ]
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Showing NP-Card for Spirobenzofuran (NP0003821)

MOL for NP0003821 (Spirobenzofuran)

3D MOL for NP0003821 (Spirobenzofuran)

3D SDF for NP0003821 (Spirobenzofuran)

3D-SDF for NP0003821 (Spirobenzofuran)

PDB for NP0003821 (Spirobenzofuran)

3D PDB for NP0003821 (Spirobenzofuran)

SMILES for NP0003821 (Spirobenzofuran)

INCHI for NP0003821 (Spirobenzofuran)

Structure for NP0003821 (Spirobenzofuran)

3D Structure for NP0003821 (Spirobenzofuran)