NP-MRD: Showing NP-Card for 9a-Hydroxy-3,8a-dimethyl-5-methylene4,4a,5,6,9,9a-hexahydronaphtho[2,3-b]furan-2(8aH)-one (NP0009972)

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Record Information

Version

2.0

Created at

2021-01-05 19:38:55 UTC

Updated at

2021-07-15 17:04:46 UTC

NP-MRD ID

NP0009972

Secondary Accession Numbers

None

Natural Product Identification

Common Name

9a-Hydroxy-3,8a-dimethyl-5-methylene4,4a,5,6,9,9a-hexahydronaphtho[2,3-b]furan-2(8aH)-one

Provided By

NPAtlas

Description

9a-Hydroxy-3,8a-dimethyl-5-methylene4,4a,5,6,9,9a-hexahydronaphtho[2,3-b]furan-2(8aH)-one is found in Commiphora myrrha, Lactarius, Lactarius piperatus and Lindera strychnifolia . Based on a literature review very few articles have been published on 9a-hydroxy-3,8a-dimethyl-5-methylidene-2H,4H,4aH,5H,6H,8aH,9H,9aH-naphtho[2,3-b]furan-2-one.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306242106543D          

 36 38  0  0  0  0            999 V2000
   -1.1977    2.8151    0.6456 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5345    1.6108    0.2511 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8750    1.3676   -0.3019 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.7979    0.2680   -1.2905 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9785   -0.7551   -1.1128 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1000   -0.8416    0.0895 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.0044   -1.2605    1.2314 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1122   -1.9301   -0.1186 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.2129   -1.5016   -0.6780 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.1405   -1.4341   -2.0945 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2660   -2.3750   -0.3835 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2684   -1.6282    0.1969 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3950   -2.0245    0.6120 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8472   -0.2388    0.2799 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6227    0.9195    0.8411 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6514   -0.1906   -0.2330 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6439    0.9082   -0.4546 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.5614    0.5087    0.3672 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.2177    3.0632    1.0656 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9112    3.6218    0.5606 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1568    2.3116   -0.8533 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6393    1.1595    0.4822 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4279    0.3184   -2.1643 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9529   -1.5559   -1.8769 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4765   -1.9910    1.8869 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3153   -0.3609    1.7668 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8920   -1.7841    0.8383 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5253   -2.6926   -0.8138 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1073   -2.4729    0.8264 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8209   -0.8131   -2.4518 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1912    1.4204    0.0488 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9148    1.6290    1.2720 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3027    0.5757    1.6582 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4466    0.9662   -1.5226 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0428    1.8423   -0.0102 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1979    0.5444    1.4399 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3  0  0  0
  2  3  1  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  1  1  0  0  0
  6  8  1  0  0  0  0
  8  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  2  0  0  0  0
 12 14  1  0  0  0  0
 14 15  1  0  0  0  0
 14 16  2  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18  2  1  0  0  0  0
 18  6  1  0  0  0  0
 16  9  1  0  0  0  0
  1 19  1  0  0  0  0
  1 20  1  0  0  0  0
  3 21  1  0  0  0  0
  3 22  1  0  0  0  0
  4 23  1  0  0  0  0
  5 24  1  0  0  0  0
  7 25  1  0  0  0  0
  7 26  1  0  0  0  0
  7 27  1  0  0  0  0
  8 28  1  0  0  0  0
  8 29  1  0  0  0  0
 10 30  1  0  0  0  0
 15 31  1  0  0  0  0
 15 32  1  0  0  0  0
 15 33  1  0  0  0  0
 17 34  1  0  0  0  0
 17 35  1  0  0  0  0
 18 36  1  1  0  0  0
M  END

     RDKit          3D

 36 38  0  0  0  0  0  0  0  0999 V2000
   -1.1977    2.8151    0.6456 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5345    1.6108    0.2511 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8750    1.3676   -0.3019 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7979    0.2680   -1.2905 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9785   -0.7551   -1.1128 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1000   -0.8416    0.0895 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.0044   -1.2605    1.2314 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1122   -1.9301   -0.1186 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2129   -1.5016   -0.6780 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.1405   -1.4341   -2.0945 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2660   -2.3750   -0.3835 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2684   -1.6282    0.1969 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3950   -2.0245    0.6120 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8472   -0.2388    0.2799 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6227    0.9195    0.8411 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6514   -0.1906   -0.2330 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6439    0.9082   -0.4546 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5614    0.5087    0.3672 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.2177    3.0632    1.0656 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9112    3.6218    0.5606 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1568    2.3116   -0.8533 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6393    1.1595    0.4822 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4279    0.3184   -2.1643 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9529   -1.5559   -1.8769 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4765   -1.9910    1.8869 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3153   -0.3609    1.7668 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8920   -1.7841    0.8383 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5253   -2.6926   -0.8138 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1073   -2.4729    0.8264 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8209   -0.8131   -2.4518 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1912    1.4204    0.0488 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9148    1.6290    1.2720 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3027    0.5757    1.6582 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4466    0.9662   -1.5226 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0428    1.8423   -0.0102 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1979    0.5444    1.4399 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3
  2  3  1  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  1  1
  6  8  1  0
  8  9  1  0
  9 10  1  6
  9 11  1  0
 11 12  1  0
 12 13  2  0
 12 14  1  0
 14 15  1  0
 14 16  2  0
 16 17  1  0
 17 18  1  0
 18  2  1  0
 18  6  1  0
 16  9  1  0
  1 19  1  0
  1 20  1  0
  3 21  1  0
  3 22  1  0
  4 23  1  0
  5 24  1  0
  7 25  1  0
  7 26  1  0
  7 27  1  0
  8 28  1  0
  8 29  1  0
 10 30  1  0
 15 31  1  0
 15 32  1  0
 15 33  1  0
 17 34  1  0
 17 35  1  0
 18 36  1  1
M  END


  Mrv1652306242106543D          

 36 38  0  0  0  0            999 V2000
   -1.1977    2.8151    0.6456 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5345    1.6108    0.2511 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8750    1.3676   -0.3019 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.7979    0.2680   -1.2905 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9785   -0.7551   -1.1128 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1000   -0.8416    0.0895 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.0044   -1.2605    1.2314 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1122   -1.9301   -0.1186 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.2129   -1.5016   -0.6780 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.1405   -1.4341   -2.0945 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2660   -2.3750   -0.3835 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2684   -1.6282    0.1969 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3950   -2.0245    0.6120 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8472   -0.2388    0.2799 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6227    0.9195    0.8411 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6514   -0.1906   -0.2330 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6439    0.9082   -0.4546 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.5614    0.5087    0.3672 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.2177    3.0632    1.0656 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9112    3.6218    0.5606 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1568    2.3116   -0.8533 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6393    1.1595    0.4822 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4279    0.3184   -2.1643 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9529   -1.5559   -1.8769 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4765   -1.9910    1.8869 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3153   -0.3609    1.7668 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8920   -1.7841    0.8383 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5253   -2.6926   -0.8138 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1073   -2.4729    0.8264 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8209   -0.8131   -2.4518 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1912    1.4204    0.0488 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9148    1.6290    1.2720 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3027    0.5757    1.6582 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4466    0.9662   -1.5226 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0428    1.8423   -0.0102 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1979    0.5444    1.4399 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3  0  0  0
  2  3  1  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  1  1  0  0  0
  6  8  1  0  0  0  0
  8  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  2  0  0  0  0
 12 14  1  0  0  0  0
 14 15  1  0  0  0  0
 14 16  2  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18  2  1  0  0  0  0
 18  6  1  0  0  0  0
 16  9  1  0  0  0  0
  1 19  1  0  0  0  0
  1 20  1  0  0  0  0
  3 21  1  0  0  0  0
  3 22  1  0  0  0  0
  4 23  1  0  0  0  0
  5 24  1  0  0  0  0
  7 25  1  0  0  0  0
  7 26  1  0  0  0  0
  7 27  1  0  0  0  0
  8 28  1  0  0  0  0
  8 29  1  0  0  0  0
 10 30  1  0  0  0  0
 15 31  1  0  0  0  0
 15 32  1  0  0  0  0
 15 33  1  0  0  0  0
 17 34  1  0  0  0  0
 17 35  1  0  0  0  0
 18 36  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0009972

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]O[C@@]12OC(=O)C(=C1C([H])([H])[C@@]1([H])C(=C([H])[H])C([H])([H])C([H])=C([H])[C@@]1(C([H])([H])[H])C2([H])[H])C([H])([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C15H18O3/c1-9-5-4-6-14(3)8-15(17)12(7-11(9)14)10(2)13(16)18-15/h4,6,11,17H,1,5,7-8H2,2-3H3/t11-,14-,15-/m0/s1

> <INCHI_KEY>
VMGUBSLDEXOUMH-UHFFFAOYSA-N

> <FORMULA>
C15H18O3

> <MOLECULAR_WEIGHT>
246.306

> <EXACT_MASS>
246.12559444

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
36

> <JCHEM_AVERAGE_POLARIZABILITY>
26.537834194357888

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(4aS,8aR,9aS)-9a-hydroxy-3,8a-dimethyl-5-methylidene-2H,4H,4aH,5H,6H,8aH,9H,9aH-naphtho[2,3-b]furan-2-one

> <ALOGPS_LOGP>
2.53

> <JCHEM_LOGP>
2.5540303926666663

> <ALOGPS_LOGS>
-2.67

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.23910579243287

> <JCHEM_PKA_STRONGEST_BASIC>
-4.443815126389862

> <JCHEM_POLAR_SURFACE_AREA>
46.53

> <JCHEM_REFRACTIVITY>
69.6206

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.24e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(4aS,8aR,9aS)-9a-hydroxy-3,8a-dimethyl-5-methylidene-4H,4aH,6H,9H-naphtho[2,3-b]furan-2-one

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 36 38  0  0  0  0  0  0  0  0999 V2000
   -1.1977    2.8151    0.6456 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5345    1.6108    0.2511 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8750    1.3676   -0.3019 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7979    0.2680   -1.2905 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9785   -0.7551   -1.1128 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1000   -0.8416    0.0895 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.0044   -1.2605    1.2314 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1122   -1.9301   -0.1186 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2129   -1.5016   -0.6780 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.1405   -1.4341   -2.0945 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2660   -2.3750   -0.3835 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2684   -1.6282    0.1969 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3950   -2.0245    0.6120 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8472   -0.2388    0.2799 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6227    0.9195    0.8411 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6514   -0.1906   -0.2330 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6439    0.9082   -0.4546 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5614    0.5087    0.3672 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.2177    3.0632    1.0656 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9112    3.6218    0.5606 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1568    2.3116   -0.8533 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6393    1.1595    0.4822 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4279    0.3184   -2.1643 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9529   -1.5559   -1.8769 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4765   -1.9910    1.8869 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3153   -0.3609    1.7668 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8920   -1.7841    0.8383 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5253   -2.6926   -0.8138 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1073   -2.4729    0.8264 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8209   -0.8131   -2.4518 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1912    1.4204    0.0488 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9148    1.6290    1.2720 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3027    0.5757    1.6582 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4466    0.9662   -1.5226 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0428    1.8423   -0.0102 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1979    0.5444    1.4399 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3
  2  3  1  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  1  1
  6  8  1  0
  8  9  1  0
  9 10  1  6
  9 11  1  0
 11 12  1  0
 12 13  2  0
 12 14  1  0
 14 15  1  0
 14 16  2  0
 16 17  1  0
 17 18  1  0
 18  2  1  0
 18  6  1  0
 16  9  1  0
  1 19  1  0
  1 20  1  0
  3 21  1  0
  3 22  1  0
  4 23  1  0
  5 24  1  0
  7 25  1  0
  7 26  1  0
  7 27  1  0
  8 28  1  0
  8 29  1  0
 10 30  1  0
 15 31  1  0
 15 32  1  0
 15 33  1  0
 17 34  1  0
 17 35  1  0
 18 36  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      -1.198   2.815   0.646  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.535   1.611   0.251  0.00  0.00           C+0
HETATM    3  C   UNK     0      -2.875   1.368  -0.302  0.00  0.00           C+0
HETATM    4  C   UNK     0      -2.798   0.268  -1.291  0.00  0.00           C+0
HETATM    5  C   UNK     0      -1.978  -0.755  -1.113  0.00  0.00           C+0
HETATM    6  C   UNK     0      -1.100  -0.842   0.090  0.00  0.00           C+0
HETATM    7  C   UNK     0      -2.004  -1.260   1.231  0.00  0.00           C+0
HETATM    8  C   UNK     0      -0.112  -1.930  -0.119  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.213  -1.502  -0.678  0.00  0.00           C+0
HETATM   10  O   UNK     0       1.141  -1.434  -2.095  0.00  0.00           O+0
HETATM   11  O   UNK     0       2.266  -2.375  -0.384  0.00  0.00           O+0
HETATM   12  C   UNK     0       3.268  -1.628   0.197  0.00  0.00           C+0
HETATM   13  O   UNK     0       4.395  -2.025   0.612  0.00  0.00           O+0
HETATM   14  C   UNK     0       2.847  -0.239   0.280  0.00  0.00           C+0
HETATM   15  C   UNK     0       3.623   0.920   0.841  0.00  0.00           C+0
HETATM   16  C   UNK     0       1.651  -0.191  -0.233  0.00  0.00           C+0
HETATM   17  C   UNK     0       0.644   0.908  -0.455  0.00  0.00           C+0
HETATM   18  C   UNK     0      -0.561   0.509   0.367  0.00  0.00           C+0
HETATM   19  H   UNK     0      -0.218   3.063   1.066  0.00  0.00           H+0
HETATM   20  H   UNK     0      -1.911   3.622   0.561  0.00  0.00           H+0
HETATM   21  H   UNK     0      -3.157   2.312  -0.853  0.00  0.00           H+0
HETATM   22  H   UNK     0      -3.639   1.159   0.482  0.00  0.00           H+0
HETATM   23  H   UNK     0      -3.428   0.318  -2.164  0.00  0.00           H+0
HETATM   24  H   UNK     0      -1.953  -1.556  -1.877  0.00  0.00           H+0
HETATM   25  H   UNK     0      -1.476  -1.991   1.887  0.00  0.00           H+0
HETATM   26  H   UNK     0      -2.315  -0.361   1.767  0.00  0.00           H+0
HETATM   27  H   UNK     0      -2.892  -1.784   0.838  0.00  0.00           H+0
HETATM   28  H   UNK     0      -0.525  -2.693  -0.814  0.00  0.00           H+0
HETATM   29  H   UNK     0       0.107  -2.473   0.826  0.00  0.00           H+0
HETATM   30  H   UNK     0       1.821  -0.813  -2.452  0.00  0.00           H+0
HETATM   31  H   UNK     0       4.191   1.420   0.049  0.00  0.00           H+0
HETATM   32  H   UNK     0       2.915   1.629   1.272  0.00  0.00           H+0
HETATM   33  H   UNK     0       4.303   0.576   1.658  0.00  0.00           H+0
HETATM   34  H   UNK     0       0.447   0.966  -1.523  0.00  0.00           H+0
HETATM   35  H   UNK     0       1.043   1.842  -0.010  0.00  0.00           H+0
HETATM   36  H   UNK     0      -0.198   0.544   1.440  0.00  0.00           H+0
CONECT    1    2   19   20                                                  
CONECT    2    1    3   18                                                  
CONECT    3    2    4   21   22                                             
CONECT    4    3    5   23                                                  
CONECT    5    4    6   24                                                  
CONECT    6    5    7    8   18                                             
CONECT    7    6   25   26   27                                             
CONECT    8    6    9   28   29                                             
CONECT    9    8   10   11   16                                             
CONECT   10    9   30                                                       
CONECT   11    9   12                                                       
CONECT   12   11   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12   15   16                                                  
CONECT   15   14   31   32   33                                             
CONECT   16   14   17    9                                                  
CONECT   17   16   18   34   35                                             
CONECT   18   17    2    6   36                                             
CONECT   19    1                                                            
CONECT   20    1                                                            
CONECT   21    3                                                            
CONECT   22    3                                                            
CONECT   23    4                                                            
CONECT   24    5                                                            
CONECT   25    7                                                            
CONECT   26    7                                                            
CONECT   27    7                                                            
CONECT   28    8                                                            
CONECT   29    8                                                            
CONECT   30   10                                                            
CONECT   31   15                                                            
CONECT   32   15                                                            
CONECT   33   15                                                            
CONECT   34   17                                                            
CONECT   35   17                                                            
CONECT   36   18                                                            
MASTER        0    0    0    0    0    0    0    0   36    0   76    0
END

RDKit          3D

36 38  0  0  0  0  0  0  0  0999 V2000
   -1.1977    2.8151    0.6456 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5345    1.6108    0.2511 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8750    1.3676   -0.3019 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7979    0.2680   -1.2905 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9785   -0.7551   -1.1128 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1000   -0.8416    0.0895 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.0044   -1.2605    1.2314 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1122   -1.9301   -0.1186 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2129   -1.5016   -0.6780 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.1405   -1.4341   -2.0945 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2660   -2.3750   -0.3835 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2684   -1.6282    0.1969 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3950   -2.0245    0.6120 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8472   -0.2388    0.2799 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6227    0.9195    0.8411 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6514   -0.1906   -0.2330 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6439    0.9082   -0.4546 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5614    0.5087    0.3672 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.2177    3.0632    1.0656 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9112    3.6218    0.5606 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1568    2.3116   -0.8533 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6393    1.1595    0.4822 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4279    0.3184   -2.1643 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9529   -1.5559   -1.8769 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4765   -1.9910    1.8869 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3153   -0.3609    1.7668 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8920   -1.7841    0.8383 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5253   -2.6926   -0.8138 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1073   -2.4729    0.8264 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8209   -0.8131   -2.4518 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1912    1.4204    0.0488 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9148    1.6290    1.2720 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3027    0.5757    1.6582 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4466    0.9662   -1.5226 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0428    1.8423   -0.0102 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1979    0.5444    1.4399 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3
  2  3  1  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  1  1
  6  8  1  0
  8  9  1  0
  9 10  1  6
  9 11  1  0
 11 12  1  0
 12 13  2  0
 12 14  1  0
 14 15  1  0
 14 16  2  0
 16 17  1  0
 17 18  1  0
 18  2  1  0
 18  6  1  0
 16  9  1  0
  1 19  1  0
  1 20  1  0
  3 21  1  0
  3 22  1  0
  4 23  1  0
  5 24  1  0
  7 25  1  0
  7 26  1  0
  7 27  1  0
  8 28  1  0
  8 29  1  0
 10 30  1  0
 15 31  1  0
 15 32  1  0
 15 33  1  0
 17 34  1  0
 17 35  1  0
 18 36  1  1
M  END

View in JSmol View NMR Assignments

Synonyms

Not Available

Chemical Formula

C₁₅H₁₈O₃

Average Mass

246.3060 Da

Monoisotopic Mass

246.12559 Da

IUPAC Name

(4aS,8aR,9aS)-9a-hydroxy-3,8a-dimethyl-5-methylidene-2H,4H,4aH,5H,6H,8aH,9H,9aH-naphtho[2,3-b]furan-2-one

Traditional Name

(4aS,8aR,9aS)-9a-hydroxy-3,8a-dimethyl-5-methylidene-4H,4aH,6H,9H-naphtho[2,3-b]furan-2-one

CAS Registry Number

Not Available

SMILES

CC1=C2CC3C(=C)CC=CC3(C)CC2(O)OC1=O

InChI Identifier

InChI=1S/C15H18O3/c1-9-5-4-6-14(3)8-15(17)12(7-11(9)14)10(2)13(16)18-15/h4,6,11,17H,1,5,7-8H2,2-3H3

InChI Key

VMGUBSLDEXOUMH-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
Commiphora myrrha	LOTUS Database	35616633
Lactarius	NPAtlas	21522471
Lactarius piperatus	LOTUS Database	35616633
Lindera aggregata	Plant	KNApSAcK

Chemical Taxonomy

Description

This compound belongs to the class of organic compounds known as eudesmanolides, secoeudesmanolides, and derivatives. These are terpenoids with a structure based on the eudesmanolide (a 3,5a,9-trimethyl-naphtho[1,2-b]furan-2-one derivative) or secoeudesmanolide (a 3,6-dimethyl-5-(pentan-2-yl)-1-benzofuran-2-one derivative) skeleton.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Terpene lactones

Direct Parent

Eudesmanolides, secoeudesmanolides, and derivatives

Alternative Parents

Substituents

Eudesmanolide
Sesquiterpenoid
Naphthofuran
2-furanone
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Dihydrofuran
Cyclic alcohol
Lactone
Hemiacetal
Carboxylic acid ester
Oxacycle
Organoheterocyclic compound
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
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	2.53	ALOGPS
logP	2.55	ChemAxon
logS	-2.7	ALOGPS
pKa (Strongest Acidic)	11.24	ChemAxon
pKa (Strongest Basic)	-4.4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	46.53 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	69.62 m³·mol⁻¹	ChemAxon
Polarizability	26.54 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

NPA012371

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

78444672

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

76046873

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Showing NP-Card for 9a-Hydroxy-3,8a-dimethyl-5-methylene4,4a,5,6,9,9a-hexahydronaphtho[2,3-b]furan-2(8aH)-one (NP0009972)

MOL for NP0009972 (9a-Hydroxy-3,8a-dimethyl-5-methylene4,4a,5,6,9,9a-hexahydronaphtho[2,3-b]furan-2(8aH)-one)

3D MOL for NP0009972 (9a-Hydroxy-3,8a-dimethyl-5-methylene4,4a,5,6,9,9a-hexahydronaphtho[2,3-b]furan-2(8aH)-one)

3D SDF for NP0009972 (9a-Hydroxy-3,8a-dimethyl-5-methylene4,4a,5,6,9,9a-hexahydronaphtho[2,3-b]furan-2(8aH)-one)

3D-SDF for NP0009972 (9a-Hydroxy-3,8a-dimethyl-5-methylene4,4a,5,6,9,9a-hexahydronaphtho[2,3-b]furan-2(8aH)-one)

PDB for NP0009972 (9a-Hydroxy-3,8a-dimethyl-5-methylene4,4a,5,6,9,9a-hexahydronaphtho[2,3-b]furan-2(8aH)-one)

3D PDB for NP0009972 (9a-Hydroxy-3,8a-dimethyl-5-methylene4,4a,5,6,9,9a-hexahydronaphtho[2,3-b]furan-2(8aH)-one)

SMILES for NP0009972 (9a-Hydroxy-3,8a-dimethyl-5-methylene4,4a,5,6,9,9a-hexahydronaphtho[2,3-b]furan-2(8aH)-one)

INCHI for NP0009972 (9a-Hydroxy-3,8a-dimethyl-5-methylene4,4a,5,6,9,9a-hexahydronaphtho[2,3-b]furan-2(8aH)-one)

Structure for NP0009972 (9a-Hydroxy-3,8a-dimethyl-5-methylene4,4a,5,6,9,9a-hexahydronaphtho[2,3-b]furan-2(8aH)-one)

3D Structure for NP0009972 (9a-Hydroxy-3,8a-dimethyl-5-methylene4,4a,5,6,9,9a-hexahydronaphtho[2,3-b]furan-2(8aH)-one)