NP-MRD: Showing NP-Card for 9α-hydroxy-5α-drim-7-ene-6-one-11,12-olide (NP0010856)

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Record Information

Version

2.0

Created at

2021-01-05 20:40:31 UTC

Updated at

2021-07-15 17:07:16 UTC

NP-MRD ID

NP0010856

Secondary Accession Numbers

None

Natural Product Identification

Common Name

9α-hydroxy-5α-drim-7-ene-6-one-11,12-olide

Provided By

NPAtlas

Description

9B-hydroxy-6,6,9a-trimethyl-1H,3H,5H,5aH,6H,7H,8H,9H,9aH,9bH-naphtho[1,2-c]furan-1,5-dione belongs to the class of organic compounds known as naphthofurans. Naphthofurans are compounds containing a furan ring fused to a naphthalene moiety. Furan is a 5 membered- ring aromatic ring with four carbon and one oxygen atoms. Naphthalene is a polycyclic aromatic hydrocarbon made up of two fused benzene rings. 9α-hydroxy-5α-drim-7-ene-6-one-11,12-olide is found in Aspergillus and Aspergillus carneus. Based on a literature review very few articles have been published on 9b-hydroxy-6,6,9a-trimethyl-1H,3H,5H,5aH,6H,7H,8H,9H,9aH,9bH-naphtho[1,2-c]furan-1,5-dione.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306242107413D          

 39 41  0  0  0  0            999 V2000
    2.5936   -0.7404    1.2899 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8637   -0.3723   -0.0183 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.6187   -1.1307   -1.0941 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2212    1.0936   -0.2321 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4659    1.8888    0.7788 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.0134    1.7782    0.6404 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.4856    0.5472   -0.0832 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7869    0.9011   -1.4985 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4243   -0.6445    0.0701 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.1101   -1.6877   -0.8392 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5871   -2.4313   -1.5740 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5639   -1.8285   -0.8505 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3834   -1.0095   -0.2146 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8502   -0.8518   -0.0119 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.0316    0.5303    0.2106 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8405    1.1408    0.5548 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7194    2.3544    0.8032 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8005    0.1406    0.5711 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.4864   -0.3557    1.8265 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9343   -0.5685    2.1661 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7185   -1.8565    1.2267 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5600   -0.2354    1.3439 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6595   -0.6807   -1.0673 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7831   -2.1881   -0.8527 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2651   -0.9156   -2.1116 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3163    1.1934    0.0284 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1233    1.4203   -1.2604 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7437    1.4771    1.7918 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7952    2.9560    0.7834 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4794    1.8791    1.6557 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3619    2.6992    0.0851 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0377    0.7108   -2.2095 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6781    0.3912   -1.9130 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0079    1.9870   -1.5481 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2166   -1.0511    1.1079 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0096   -2.6428   -1.4052 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1857   -1.4648    0.8270 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4264   -1.1237   -0.9142 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7068   -1.3096    1.9371 H   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  1  0  0  0
  2  3  1  0  0  0  0
  2  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  6  0  0  0
  7  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 10 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 16 18  1  0  0  0  0
 18 19  1  1  0  0  0
  9  2  1  0  0  0  0
 18 13  1  0  0  0  0
 18  7  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
  3 24  1  0  0  0  0
  3 25  1  0  0  0  0
  4 26  1  0  0  0  0
  4 27  1  0  0  0  0
  5 28  1  0  0  0  0
  5 29  1  0  0  0  0
  6 30  1  0  0  0  0
  6 31  1  0  0  0  0
  8 32  1  0  0  0  0
  8 33  1  0  0  0  0
  8 34  1  0  0  0  0
  9 35  1  1  0  0  0
 12 36  1  0  0  0  0
 14 37  1  0  0  0  0
 14 38  1  0  0  0  0
 19 39  1  0  0  0  0
M  END

     RDKit          3D

 39 41  0  0  0  0  0  0  0  0999 V2000
    2.5936   -0.7404    1.2899 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8637   -0.3723   -0.0183 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.6187   -1.1307   -1.0941 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2212    1.0936   -0.2321 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4659    1.8888    0.7788 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0134    1.7782    0.6404 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4856    0.5472   -0.0832 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7869    0.9011   -1.4985 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4243   -0.6445    0.0701 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.1101   -1.6877   -0.8392 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5871   -2.4313   -1.5740 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5639   -1.8285   -0.8505 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3834   -1.0095   -0.2146 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8502   -0.8518   -0.0119 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0316    0.5303    0.2106 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8405    1.1408    0.5548 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7194    2.3544    0.8032 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8005    0.1406    0.5711 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.4864   -0.3557    1.8265 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9343   -0.5685    2.1661 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7185   -1.8565    1.2267 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5600   -0.2354    1.3439 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6595   -0.6807   -1.0673 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7831   -2.1881   -0.8527 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2651   -0.9156   -2.1116 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3163    1.1934    0.0284 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1233    1.4203   -1.2604 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7437    1.4771    1.7918 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7952    2.9560    0.7834 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4794    1.8791    1.6557 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3619    2.6992    0.0851 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0377    0.7108   -2.2095 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6781    0.3912   -1.9130 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0079    1.9870   -1.5481 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2166   -1.0511    1.1079 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0096   -2.6428   -1.4052 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1857   -1.4648    0.8270 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4264   -1.1237   -0.9142 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7068   -1.3096    1.9371 H   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  1
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  6
  7  9  1  0
  9 10  1  0
 10 11  2  0
 10 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  2  0
 16 18  1  0
 18 19  1  1
  9  2  1  0
 18 13  1  0
 18  7  1  0
  1 20  1  0
  1 21  1  0
  1 22  1  0
  3 23  1  0
  3 24  1  0
  3 25  1  0
  4 26  1  0
  4 27  1  0
  5 28  1  0
  5 29  1  0
  6 30  1  0
  6 31  1  0
  8 32  1  0
  8 33  1  0
  8 34  1  0
  9 35  1  1
 12 36  1  0
 14 37  1  0
 14 38  1  0
 19 39  1  0
M  END


  Mrv1652306242107413D          

 39 41  0  0  0  0            999 V2000
    2.5936   -0.7404    1.2899 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8637   -0.3723   -0.0183 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.6187   -1.1307   -1.0941 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2212    1.0936   -0.2321 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4659    1.8888    0.7788 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.0134    1.7782    0.6404 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.4856    0.5472   -0.0832 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7869    0.9011   -1.4985 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4243   -0.6445    0.0701 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.1101   -1.6877   -0.8392 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5871   -2.4313   -1.5740 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5639   -1.8285   -0.8505 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3834   -1.0095   -0.2146 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8502   -0.8518   -0.0119 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.0316    0.5303    0.2106 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8405    1.1408    0.5548 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7194    2.3544    0.8032 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8005    0.1406    0.5711 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.4864   -0.3557    1.8265 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9343   -0.5685    2.1661 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7185   -1.8565    1.2267 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5600   -0.2354    1.3439 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6595   -0.6807   -1.0673 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7831   -2.1881   -0.8527 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2651   -0.9156   -2.1116 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3163    1.1934    0.0284 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1233    1.4203   -1.2604 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7437    1.4771    1.7918 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7952    2.9560    0.7834 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4794    1.8791    1.6557 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3619    2.6992    0.0851 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0377    0.7108   -2.2095 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6781    0.3912   -1.9130 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0079    1.9870   -1.5481 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2166   -1.0511    1.1079 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0096   -2.6428   -1.4052 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1857   -1.4648    0.8270 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4264   -1.1237   -0.9142 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7068   -1.3096    1.9371 H   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  1  0  0  0
  2  3  1  0  0  0  0
  2  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  6  0  0  0
  7  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 10 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 16 18  1  0  0  0  0
 18 19  1  1  0  0  0
  9  2  1  0  0  0  0
 18 13  1  0  0  0  0
 18  7  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
  3 24  1  0  0  0  0
  3 25  1  0  0  0  0
  4 26  1  0  0  0  0
  4 27  1  0  0  0  0
  5 28  1  0  0  0  0
  5 29  1  0  0  0  0
  6 30  1  0  0  0  0
  6 31  1  0  0  0  0
  8 32  1  0  0  0  0
  8 33  1  0  0  0  0
  8 34  1  0  0  0  0
  9 35  1  1  0  0  0
 12 36  1  0  0  0  0
 14 37  1  0  0  0  0
 14 38  1  0  0  0  0
 19 39  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0010856

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]O[C@]12C(=O)OC([H])([H])C1=C([H])C(=O)[C@@]1([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])C([H])([H])C([H])([H])[C@]21C([H])([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C15H20O4/c1-13(2)5-4-6-14(3)11(13)10(16)7-9-8-19-12(17)15(9,14)18/h7,11,18H,4-6,8H2,1-3H3/t11-,14-,15-/m0/s1

> <INCHI_KEY>
LGVCGEBNSHQLLO-UHFFFAOYSA-N

> <FORMULA>
C15H20O4

> <MOLECULAR_WEIGHT>
264.321

> <EXACT_MASS>
264.136159124

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
39

> <JCHEM_AVERAGE_POLARIZABILITY>
27.153302164518905

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(5aS,9aS,9bS)-9b-hydroxy-6,6,9a-trimethyl-1H,3H,5H,5aH,6H,7H,8H,9H,9aH,9bH-naphtho[1,2-c]furan-1,5-dione

> <ALOGPS_LOGP>
1.52

> <JCHEM_LOGP>
1.8868359826666654

> <ALOGPS_LOGS>
-2.34

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.937481626311605

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.39178918826118

> <JCHEM_PKA_STRONGEST_BASIC>
-4.374078265011609

> <JCHEM_POLAR_SURFACE_AREA>
63.60000000000001

> <JCHEM_REFRACTIVITY>
69.4128

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.21e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(5aS,9aS,9bS)-9b-hydroxy-6,6,9a-trimethyl-3H,5aH,7H,8H,9H-naphtho[1,2-c]furan-1,5-dione

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 39 41  0  0  0  0  0  0  0  0999 V2000
    2.5936   -0.7404    1.2899 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8637   -0.3723   -0.0183 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.6187   -1.1307   -1.0941 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2212    1.0936   -0.2321 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4659    1.8888    0.7788 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0134    1.7782    0.6404 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4856    0.5472   -0.0832 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7869    0.9011   -1.4985 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4243   -0.6445    0.0701 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.1101   -1.6877   -0.8392 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5871   -2.4313   -1.5740 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5639   -1.8285   -0.8505 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3834   -1.0095   -0.2146 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8502   -0.8518   -0.0119 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0316    0.5303    0.2106 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8405    1.1408    0.5548 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7194    2.3544    0.8032 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8005    0.1406    0.5711 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.4864   -0.3557    1.8265 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9343   -0.5685    2.1661 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7185   -1.8565    1.2267 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5600   -0.2354    1.3439 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6595   -0.6807   -1.0673 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7831   -2.1881   -0.8527 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2651   -0.9156   -2.1116 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3163    1.1934    0.0284 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1233    1.4203   -1.2604 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7437    1.4771    1.7918 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7952    2.9560    0.7834 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4794    1.8791    1.6557 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3619    2.6992    0.0851 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0377    0.7108   -2.2095 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6781    0.3912   -1.9130 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0079    1.9870   -1.5481 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2166   -1.0511    1.1079 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0096   -2.6428   -1.4052 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1857   -1.4648    0.8270 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4264   -1.1237   -0.9142 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7068   -1.3096    1.9371 H   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  1
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  6
  7  9  1  0
  9 10  1  0
 10 11  2  0
 10 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  2  0
 16 18  1  0
 18 19  1  1
  9  2  1  0
 18 13  1  0
 18  7  1  0
  1 20  1  0
  1 21  1  0
  1 22  1  0
  3 23  1  0
  3 24  1  0
  3 25  1  0
  4 26  1  0
  4 27  1  0
  5 28  1  0
  5 29  1  0
  6 30  1  0
  6 31  1  0
  8 32  1  0
  8 33  1  0
  8 34  1  0
  9 35  1  1
 12 36  1  0
 14 37  1  0
 14 38  1  0
 19 39  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       2.594  -0.740   1.290  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.864  -0.372  -0.018  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.619  -1.131  -1.094  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.221   1.094  -0.232  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.466   1.889   0.779  0.00  0.00           C+0
HETATM    6  C   UNK     0      -0.013   1.778   0.640  0.00  0.00           C+0
HETATM    7  C   UNK     0      -0.486   0.547  -0.083  0.00  0.00           C+0
HETATM    8  C   UNK     0      -0.787   0.901  -1.498  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.424  -0.645   0.070  0.00  0.00           C+0
HETATM   10  C   UNK     0      -0.110  -1.688  -0.839  0.00  0.00           C+0
HETATM   11  O   UNK     0       0.587  -2.431  -1.574  0.00  0.00           O+0
HETATM   12  C   UNK     0      -1.564  -1.829  -0.851  0.00  0.00           C+0
HETATM   13  C   UNK     0      -2.383  -1.010  -0.215  0.00  0.00           C+0
HETATM   14  C   UNK     0      -3.850  -0.852  -0.012  0.00  0.00           C+0
HETATM   15  O   UNK     0      -4.032   0.530   0.211  0.00  0.00           O+0
HETATM   16  C   UNK     0      -2.841   1.141   0.555  0.00  0.00           C+0
HETATM   17  O   UNK     0      -2.719   2.354   0.803  0.00  0.00           O+0
HETATM   18  C   UNK     0      -1.801   0.141   0.571  0.00  0.00           C+0
HETATM   19  O   UNK     0      -1.486  -0.356   1.827  0.00  0.00           O+0
HETATM   20  H   UNK     0       1.934  -0.569   2.166  0.00  0.00           H+0
HETATM   21  H   UNK     0       2.719  -1.857   1.227  0.00  0.00           H+0
HETATM   22  H   UNK     0       3.560  -0.235   1.344  0.00  0.00           H+0
HETATM   23  H   UNK     0       3.660  -0.681  -1.067  0.00  0.00           H+0
HETATM   24  H   UNK     0       2.783  -2.188  -0.853  0.00  0.00           H+0
HETATM   25  H   UNK     0       2.265  -0.916  -2.112  0.00  0.00           H+0
HETATM   26  H   UNK     0       3.316   1.193   0.028  0.00  0.00           H+0
HETATM   27  H   UNK     0       2.123   1.420  -1.260  0.00  0.00           H+0
HETATM   28  H   UNK     0       1.744   1.477   1.792  0.00  0.00           H+0
HETATM   29  H   UNK     0       1.795   2.956   0.783  0.00  0.00           H+0
HETATM   30  H   UNK     0      -0.479   1.879   1.656  0.00  0.00           H+0
HETATM   31  H   UNK     0      -0.362   2.699   0.085  0.00  0.00           H+0
HETATM   32  H   UNK     0       0.038   0.711  -2.209  0.00  0.00           H+0
HETATM   33  H   UNK     0      -1.678   0.391  -1.913  0.00  0.00           H+0
HETATM   34  H   UNK     0      -1.008   1.987  -1.548  0.00  0.00           H+0
HETATM   35  H   UNK     0       0.217  -1.051   1.108  0.00  0.00           H+0
HETATM   36  H   UNK     0      -2.010  -2.643  -1.405  0.00  0.00           H+0
HETATM   37  H   UNK     0      -4.186  -1.465   0.827  0.00  0.00           H+0
HETATM   38  H   UNK     0      -4.426  -1.124  -0.914  0.00  0.00           H+0
HETATM   39  H   UNK     0      -1.707  -1.310   1.937  0.00  0.00           H+0
CONECT    1    2   20   21   22                                             
CONECT    2    1    3    4    9                                             
CONECT    3    2   23   24   25                                             
CONECT    4    2    5   26   27                                             
CONECT    5    4    6   28   29                                             
CONECT    6    5    7   30   31                                             
CONECT    7    6    8    9   18                                             
CONECT    8    7   32   33   34                                             
CONECT    9    7   10    2   35                                             
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10   13   36                                                  
CONECT   13   12   14   18                                                  
CONECT   14   13   15   37   38                                             
CONECT   15   14   16                                                       
CONECT   16   15   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16   19   13    7                                             
CONECT   19   18   39                                                       
CONECT   20    1                                                            
CONECT   21    1                                                            
CONECT   22    1                                                            
CONECT   23    3                                                            
CONECT   24    3                                                            
CONECT   25    3                                                            
CONECT   26    4                                                            
CONECT   27    4                                                            
CONECT   28    5                                                            
CONECT   29    5                                                            
CONECT   30    6                                                            
CONECT   31    6                                                            
CONECT   32    8                                                            
CONECT   33    8                                                            
CONECT   34    8                                                            
CONECT   35    9                                                            
CONECT   36   12                                                            
CONECT   37   14                                                            
CONECT   38   14                                                            
CONECT   39   19                                                            
MASTER        0    0    0    0    0    0    0    0   39    0   82    0
END

RDKit          3D

39 41  0  0  0  0  0  0  0  0999 V2000
    2.5936   -0.7404    1.2899 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8637   -0.3723   -0.0183 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.6187   -1.1307   -1.0941 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2212    1.0936   -0.2321 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4659    1.8888    0.7788 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0134    1.7782    0.6404 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4856    0.5472   -0.0832 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7869    0.9011   -1.4985 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4243   -0.6445    0.0701 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.1101   -1.6877   -0.8392 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5871   -2.4313   -1.5740 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5639   -1.8285   -0.8505 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3834   -1.0095   -0.2146 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8502   -0.8518   -0.0119 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0316    0.5303    0.2106 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8405    1.1408    0.5548 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7194    2.3544    0.8032 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8005    0.1406    0.5711 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.4864   -0.3557    1.8265 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9343   -0.5685    2.1661 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7185   -1.8565    1.2267 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5600   -0.2354    1.3439 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6595   -0.6807   -1.0673 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7831   -2.1881   -0.8527 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2651   -0.9156   -2.1116 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3163    1.1934    0.0284 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1233    1.4203   -1.2604 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7437    1.4771    1.7918 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7952    2.9560    0.7834 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4794    1.8791    1.6557 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3619    2.6992    0.0851 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0377    0.7108   -2.2095 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6781    0.3912   -1.9130 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0079    1.9870   -1.5481 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2166   -1.0511    1.1079 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0096   -2.6428   -1.4052 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1857   -1.4648    0.8270 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4264   -1.1237   -0.9142 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7068   -1.3096    1.9371 H   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  1
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  6
  7  9  1  0
  9 10  1  0
 10 11  2  0
 10 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  2  0
 16 18  1  0
 18 19  1  1
  9  2  1  0
 18 13  1  0
 18  7  1  0
  1 20  1  0
  1 21  1  0
  1 22  1  0
  3 23  1  0
  3 24  1  0
  3 25  1  0
  4 26  1  0
  4 27  1  0
  5 28  1  0
  5 29  1  0
  6 30  1  0
  6 31  1  0
  8 32  1  0
  8 33  1  0
  8 34  1  0
  9 35  1  1
 12 36  1  0
 14 37  1  0
 14 38  1  0
 19 39  1  0
M  END

View in JSmol View NMR Assignments

Synonyms

Value	Source
9a-Hydroxy-5a-drim-7-ene-6-one-11,12-olide	Generator
9Α-hydroxy-5α-drim-7-ene-6-one-11,12-olide	Generator

Chemical Formula

C₁₅H₂₀O₄

Average Mass

264.3210 Da

Monoisotopic Mass

264.13616 Da

IUPAC Name

(5aS,9aS,9bS)-9b-hydroxy-6,6,9a-trimethyl-1H,3H,5H,5aH,6H,7H,8H,9H,9aH,9bH-naphtho[1,2-c]furan-1,5-dione

Traditional Name

(5aS,9aS,9bS)-9b-hydroxy-6,6,9a-trimethyl-3H,5aH,7H,8H,9H-naphtho[1,2-c]furan-1,5-dione

CAS Registry Number

Not Available

SMILES

CC1(C)CCCC2(C)C1C(=O)C=C1COC(=O)C21O

InChI Identifier

InChI=1S/C15H20O4/c1-13(2)5-4-6-14(3)11(13)10(16)7-9-8-19-12(17)15(9,14)18/h7,11,18H,4-6,8H2,1-3H3

InChI Key

LGVCGEBNSHQLLO-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
Aspergillus	NPAtlas	22658281
Aspergillus carneus	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as naphthofurans. Naphthofurans are compounds containing a furan ring fused to a naphthalene moiety. Furan is a 5 membered- ring aromatic ring with four carbon and one oxygen atoms. Naphthalene is a polycyclic aromatic hydrocarbon made up of two fused benzene rings.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Naphthofurans

Sub Class

Not Available

Direct Parent

Naphthofurans

Alternative Parents

Substituents

Naphthofuran
Cyclohexenone
Gamma butyrolactone
Tertiary alcohol
Tetrahydrofuran
Carboxylic acid ester
Ketone
Lactone
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Oxacycle
Organic oxide
Carbonyl group
Organic oxygen compound
Alcohol
Organooxygen compound
Hydrocarbon derivative
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic 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	1.52	ALOGPS
logP	1.89	ChemAxon
logS	-2.3	ALOGPS
pKa (Strongest Acidic)	11.39	ChemAxon
pKa (Strongest Basic)	-4.4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	63.6 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	69.41 m³·mol⁻¹	ChemAxon
Polarizability	27.15 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

NPA016644

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

78444737

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

139587729

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Showing NP-Card for 9α-hydroxy-5α-drim-7-ene-6-one-11,12-olide (NP0010856)

MOL for NP0010856 (9α-hydroxy-5α-drim-7-ene-6-one-11,12-olide)

3D MOL for NP0010856 (9α-hydroxy-5α-drim-7-ene-6-one-11,12-olide)

3D SDF for NP0010856 (9α-hydroxy-5α-drim-7-ene-6-one-11,12-olide)

3D-SDF for NP0010856 (9α-hydroxy-5α-drim-7-ene-6-one-11,12-olide)

PDB for NP0010856 (9α-hydroxy-5α-drim-7-ene-6-one-11,12-olide)

3D PDB for NP0010856 (9α-hydroxy-5α-drim-7-ene-6-one-11,12-olide)

SMILES for NP0010856 (9α-hydroxy-5α-drim-7-ene-6-one-11,12-olide)

INCHI for NP0010856 (9α-hydroxy-5α-drim-7-ene-6-one-11,12-olide)

Structure for NP0010856 (9α-hydroxy-5α-drim-7-ene-6-one-11,12-olide)

3D Structure for NP0010856 (9α-hydroxy-5α-drim-7-ene-6-one-11,12-olide)