NP-MRD: Showing NP-Card for 4aalphaH-3,5alpha,8abeta-trimethyl-4,4a,8a,9-tetrahydronaphtho[2,3b]-fura+ (NP0028974)

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Record Information

Version

2.0

Created at

2021-06-19 20:43:05 UTC

Updated at

2021-06-29 23:56:04 UTC

NP-MRD ID

NP0028974

Secondary Accession Numbers

None

Natural Product Identification

Common Name

4aalphaH-3,5alpha,8abeta-trimethyl-4,4a,8a,9-tetrahydronaphtho[2,3b]-fura+

Provided By

JEOL Database JEOL Logo

Description

4aalphaH-3,5alpha,8abeta-trimethyl-4,4a,8a,9-tetrahydronaphtho[2,3b]-fura+ is found in Siphonochilus aethiopicus. 4aalphaH-3,5alpha,8abeta-trimethyl-4,4a,8a,9-tetrahydronaphtho[2,3b]-fura+ was first documented in 2002 (Holzafel, C. W., et al.). Based on a literature review very few articles have been published on SCHEMBL2604750.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306192122433D          

 35 37  0  0  0  0            999 V2000
   -2.1297   -1.0320    4.6026 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7546    0.0604    3.6750 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4521    1.3701    4.0048 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1547    2.1015    2.8970 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2687    1.2545    1.8513 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6276   -0.0077    2.2606 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8286   -1.1242    1.2991 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.2332   -0.7727   -0.0974 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.6316   -1.8218   -1.1682 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.0380   -3.2012   -0.8551 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1930   -1.3930   -2.5475 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8333   -0.1474   -2.8812 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9097    0.9651   -1.9025 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5024    2.0734   -2.2453 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5708    0.6994   -0.5495 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.0854    0.9355   -0.7313 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9975    1.7278    0.4753 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.3753   -1.8249    4.5828 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2150   -0.6695    5.6320 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0934   -1.4646    4.3152 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4072    1.9120    4.9394 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3480   -2.0259    1.6946 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9012   -1.3348    1.2129 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1360   -0.8177    0.0079 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7232   -1.9327   -1.1899 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2777   -3.9223   -1.6452 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4422   -3.6067    0.0774 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0530   -3.1566   -0.7633 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1719   -2.1556   -3.3246 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5058    0.1149   -3.8808 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5173    0.2728   -1.4883 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2803    1.9606   -1.0691 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6426    0.7858    0.1985 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    2.7234    0.3184 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0889    1.8247    0.3522 H   0  0  0  0  0  0  0  0  0  0  0  0
  5 17  1  0  0  0  0
  5  6  2  0  0  0  0
  9  8  1  0  0  0  0
 15 13  1  0  0  0  0
 15  8  1  0  0  0  0
 12 11  2  0  0  0  0
  6  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
 12 13  1  0  0  0  0
  2  1  1  0  0  0  0
 11  9  1  0  0  0  0
 13 14  2  0  0  0  0
 15 17  1  0  0  0  0
  8 24  1  1  0  0  0
  8  7  1  0  0  0  0
  9 10  1  0  0  0  0
  7  6  1  0  0  0  0
 15 16  1  6  0  0  0
 12 30  1  0  0  0  0
 11 29  1  0  0  0  0
  9 25  1  6  0  0  0
  7 22  1  0  0  0  0
  7 23  1  0  0  0  0
 17 34  1  0  0  0  0
 17 35  1  0  0  0  0
  3 21  1  0  0  0  0
  1 18  1  0  0  0  0
  1 19  1  0  0  0  0
  1 20  1  0  0  0  0
 10 26  1  0  0  0  0
 10 27  1  0  0  0  0
 10 28  1  0  0  0  0
 16 31  1  0  0  0  0
 16 32  1  0  0  0  0
 16 33  1  0  0  0  0
M  END

     RDKit          3D

 35 37  0  0  0  0  0  0  0  0999 V2000
   -2.1297   -1.0320    4.6026 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7546    0.0604    3.6750 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4521    1.3701    4.0048 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1547    2.1015    2.8970 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2687    1.2545    1.8513 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6276   -0.0077    2.2606 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8286   -1.1242    1.2991 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2332   -0.7727   -0.0974 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.6316   -1.8218   -1.1682 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.0380   -3.2012   -0.8551 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1930   -1.3930   -2.5475 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8333   -0.1474   -2.8812 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9097    0.9651   -1.9025 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5024    2.0734   -2.2453 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5708    0.6994   -0.5495 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.0854    0.9355   -0.7313 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9975    1.7278    0.4753 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3753   -1.8249    4.5828 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2150   -0.6695    5.6320 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0934   -1.4646    4.3152 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4072    1.9120    4.9394 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3480   -2.0259    1.6946 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9012   -1.3348    1.2129 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1360   -0.8177    0.0079 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7232   -1.9327   -1.1899 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2777   -3.9223   -1.6452 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4422   -3.6067    0.0774 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0530   -3.1566   -0.7633 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1719   -2.1556   -3.3246 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5058    0.1149   -3.8808 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5173    0.2728   -1.4883 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2803    1.9606   -1.0691 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6426    0.7858    0.1985 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    2.7234    0.3184 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0889    1.8247    0.3522 H   0  0  0  0  0  0  0  0  0  0  0  0
  5 17  1  0
  5  6  2  0
  9  8  1  0
 15 13  1  0
 15  8  1  0
 12 11  2  0
  6  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  1  0
 12 13  1  0
  2  1  1  0
 11  9  1  0
 13 14  2  0
 15 17  1  0
  8 24  1  1
  8  7  1  0
  9 10  1  0
  7  6  1  0
 15 16  1  6
 12 30  1  0
 11 29  1  0
  9 25  1  6
  7 22  1  0
  7 23  1  0
 17 34  1  0
 17 35  1  0
  3 21  1  0
  1 18  1  0
  1 19  1  0
  1 20  1  0
 10 26  1  0
 10 27  1  0
 10 28  1  0
 16 31  1  0
 16 32  1  0
 16 33  1  0
M  END


  Mrv1652306192122433D          

 35 37  0  0  0  0            999 V2000
   -2.1297   -1.0320    4.6026 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7546    0.0604    3.6750 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4521    1.3701    4.0048 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1547    2.1015    2.8970 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2687    1.2545    1.8513 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6276   -0.0077    2.2606 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8286   -1.1242    1.2991 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.2332   -0.7727   -0.0974 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.6316   -1.8218   -1.1682 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.0380   -3.2012   -0.8551 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1930   -1.3930   -2.5475 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8333   -0.1474   -2.8812 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9097    0.9651   -1.9025 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5024    2.0734   -2.2453 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5708    0.6994   -0.5495 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.0854    0.9355   -0.7313 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9975    1.7278    0.4753 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.3753   -1.8249    4.5828 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2150   -0.6695    5.6320 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0934   -1.4646    4.3152 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4072    1.9120    4.9394 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3480   -2.0259    1.6946 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9012   -1.3348    1.2129 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1360   -0.8177    0.0079 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7232   -1.9327   -1.1899 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2777   -3.9223   -1.6452 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4422   -3.6067    0.0774 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0530   -3.1566   -0.7633 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1719   -2.1556   -3.3246 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5058    0.1149   -3.8808 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5173    0.2728   -1.4883 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2803    1.9606   -1.0691 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6426    0.7858    0.1985 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    2.7234    0.3184 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0889    1.8247    0.3522 H   0  0  0  0  0  0  0  0  0  0  0  0
  5 17  1  0  0  0  0
  5  6  2  0  0  0  0
  9  8  1  0  0  0  0
 15 13  1  0  0  0  0
 15  8  1  0  0  0  0
 12 11  2  0  0  0  0
  6  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
 12 13  1  0  0  0  0
  2  1  1  0  0  0  0
 11  9  1  0  0  0  0
 13 14  2  0  0  0  0
 15 17  1  0  0  0  0
  8 24  1  1  0  0  0
  8  7  1  0  0  0  0
  9 10  1  0  0  0  0
  7  6  1  0  0  0  0
 15 16  1  6  0  0  0
 12 30  1  0  0  0  0
 11 29  1  0  0  0  0
  9 25  1  6  0  0  0
  7 22  1  0  0  0  0
  7 23  1  0  0  0  0
 17 34  1  0  0  0  0
 17 35  1  0  0  0  0
  3 21  1  0  0  0  0
  1 18  1  0  0  0  0
  1 19  1  0  0  0  0
  1 20  1  0  0  0  0
 10 26  1  0  0  0  0
 10 27  1  0  0  0  0
 10 28  1  0  0  0  0
 16 31  1  0  0  0  0
 16 32  1  0  0  0  0
 16 33  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0028974

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]C1=C(C2=C(O1)C([H])([H])[C@]1(C(=O)C([H])=C([H])[C@@]([H])(C([H])([H])[H])[C@]1([H])C2([H])[H])C([H])([H])[H])C([H])([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C15H18O2/c1-9-4-5-14(16)15(3)7-13-11(6-12(9)15)10(2)8-17-13/h4-5,8-9,12H,6-7H2,1-3H3/t9-,12+,15-/m1/s1

> <INCHI_KEY>
IDGRBNKTZISWPG-MURWCNHISA-N

> <FORMULA>
C15H18O2

> <MOLECULAR_WEIGHT>
230.307

> <EXACT_MASS>
230.13067982

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_ATOM_COUNT>
35

> <JCHEM_AVERAGE_POLARIZABILITY>
26.27680750591304

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <ALOGPS_LOGP>
3.44

> <JCHEM_LOGP>
3.7603165600000006

> <ALOGPS_LOGS>
-4.02

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
18.851895040125406

> <JCHEM_PKA_STRONGEST_BASIC>
-2.801404220939433

> <JCHEM_POLAR_SURFACE_AREA>
30.21

> <JCHEM_REFRACTIVITY>
68.43350000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.22e-02 g/l

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

> <JCHEM_VEBER_RULE>
1

$$$$

     RDKit          3D

 35 37  0  0  0  0  0  0  0  0999 V2000
   -2.1297   -1.0320    4.6026 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7546    0.0604    3.6750 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4521    1.3701    4.0048 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1547    2.1015    2.8970 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2687    1.2545    1.8513 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6276   -0.0077    2.2606 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8286   -1.1242    1.2991 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2332   -0.7727   -0.0974 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.6316   -1.8218   -1.1682 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.0380   -3.2012   -0.8551 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1930   -1.3930   -2.5475 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8333   -0.1474   -2.8812 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9097    0.9651   -1.9025 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5024    2.0734   -2.2453 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5708    0.6994   -0.5495 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.0854    0.9355   -0.7313 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9975    1.7278    0.4753 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3753   -1.8249    4.5828 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2150   -0.6695    5.6320 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0934   -1.4646    4.3152 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4072    1.9120    4.9394 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3480   -2.0259    1.6946 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9012   -1.3348    1.2129 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1360   -0.8177    0.0079 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7232   -1.9327   -1.1899 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2777   -3.9223   -1.6452 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4422   -3.6067    0.0774 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0530   -3.1566   -0.7633 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1719   -2.1556   -3.3246 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5058    0.1149   -3.8808 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5173    0.2728   -1.4883 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2803    1.9606   -1.0691 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6426    0.7858    0.1985 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    2.7234    0.3184 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0889    1.8247    0.3522 H   0  0  0  0  0  0  0  0  0  0  0  0
  5 17  1  0
  5  6  2  0
  9  8  1  0
 15 13  1  0
 15  8  1  0
 12 11  2  0
  6  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  1  0
 12 13  1  0
  2  1  1  0
 11  9  1  0
 13 14  2  0
 15 17  1  0
  8 24  1  1
  8  7  1  0
  9 10  1  0
  7  6  1  0
 15 16  1  6
 12 30  1  0
 11 29  1  0
  9 25  1  6
  7 22  1  0
  7 23  1  0
 17 34  1  0
 17 35  1  0
  3 21  1  0
  1 18  1  0
  1 19  1  0
  1 20  1  0
 10 26  1  0
 10 27  1  0
 10 28  1  0
 16 31  1  0
 16 32  1  0
 16 33  1  0
M  END

HEADER    PROTEIN                                 19-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   19-JUN-21         0                                  
HETATM    1  C   UNK     0      -2.130  -1.032   4.603  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.755   0.060   3.675  0.00  0.00           C+0
HETATM    3  C   UNK     0      -1.452   1.370   4.005  0.00  0.00           C+0
HETATM    4  O   UNK     0      -1.155   2.102   2.897  0.00  0.00           O+0
HETATM    5  C   UNK     0      -1.269   1.254   1.851  0.00  0.00           C+0
HETATM    6  C   UNK     0      -1.628  -0.008   2.261  0.00  0.00           C+0
HETATM    7  C   UNK     0      -1.829  -1.124   1.299  0.00  0.00           C+0
HETATM    8  C   UNK     0      -1.233  -0.773  -0.097  0.00  0.00           C+0
HETATM    9  C   UNK     0      -1.632  -1.822  -1.168  0.00  0.00           C+0
HETATM   10  C   UNK     0      -1.038  -3.201  -0.855  0.00  0.00           C+0
HETATM   11  C   UNK     0      -1.193  -1.393  -2.547  0.00  0.00           C+0
HETATM   12  C   UNK     0      -0.833  -0.147  -2.881  0.00  0.00           C+0
HETATM   13  C   UNK     0      -0.910   0.965  -1.903  0.00  0.00           C+0
HETATM   14  O   UNK     0      -0.502   2.073  -2.245  0.00  0.00           O+0
HETATM   15  C   UNK     0      -1.571   0.699  -0.550  0.00  0.00           C+0
HETATM   16  C   UNK     0      -3.085   0.936  -0.731  0.00  0.00           C+0
HETATM   17  C   UNK     0      -0.998   1.728   0.475  0.00  0.00           C+0
HETATM   18  H   UNK     0      -1.375  -1.825   4.583  0.00  0.00           H+0
HETATM   19  H   UNK     0      -2.215  -0.670   5.632  0.00  0.00           H+0
HETATM   20  H   UNK     0      -3.093  -1.465   4.315  0.00  0.00           H+0
HETATM   21  H   UNK     0      -1.407   1.912   4.939  0.00  0.00           H+0
HETATM   22  H   UNK     0      -1.348  -2.026   1.695  0.00  0.00           H+0
HETATM   23  H   UNK     0      -2.901  -1.335   1.213  0.00  0.00           H+0
HETATM   24  H   UNK     0      -0.136  -0.818   0.008  0.00  0.00           H+0
HETATM   25  H   UNK     0      -2.723  -1.933  -1.190  0.00  0.00           H+0
HETATM   26  H   UNK     0      -1.278  -3.922  -1.645  0.00  0.00           H+0
HETATM   27  H   UNK     0      -1.442  -3.607   0.077  0.00  0.00           H+0
HETATM   28  H   UNK     0       0.053  -3.157  -0.763  0.00  0.00           H+0
HETATM   29  H   UNK     0      -1.172  -2.156  -3.325  0.00  0.00           H+0
HETATM   30  H   UNK     0      -0.506   0.115  -3.881  0.00  0.00           H+0
HETATM   31  H   UNK     0      -3.517   0.273  -1.488  0.00  0.00           H+0
HETATM   32  H   UNK     0      -3.280   1.961  -1.069  0.00  0.00           H+0
HETATM   33  H   UNK     0      -3.643   0.786   0.199  0.00  0.00           H+0
HETATM   34  H   UNK     0      -1.429   2.723   0.318  0.00  0.00           H+0
HETATM   35  H   UNK     0       0.089   1.825   0.352  0.00  0.00           H+0
CONECT    1    2   18   19   20                                             
CONECT    2    6    3    1                                                  
CONECT    3    2    4   21                                                  
CONECT    4    3    5                                                       
CONECT    5   17    6    4                                                  
CONECT    6    5    2    7                                                  
CONECT    7    8    6   22   23                                             
CONECT    8    9   15   24    7                                             
CONECT    9    8   11   10   25                                             
CONECT   10    9   26   27   28                                             
CONECT   11   12    9   29                                                  
CONECT   12   11   13   30                                                  
CONECT   13   15   12   14                                                  
CONECT   14   13                                                            
CONECT   15   13    8   17   16                                             
CONECT   16   15   31   32   33                                             
CONECT   17    5   15   34   35                                             
CONECT   18    1                                                            
CONECT   19    1                                                            
CONECT   20    1                                                            
CONECT   21    3                                                            
CONECT   22    7                                                            
CONECT   23    7                                                            
CONECT   24    8                                                            
CONECT   25    9                                                            
CONECT   26   10                                                            
CONECT   27   10                                                            
CONECT   28   10                                                            
CONECT   29   11                                                            
CONECT   30   12                                                            
CONECT   31   16                                                            
CONECT   32   16                                                            
CONECT   33   16                                                            
CONECT   34   17                                                            
CONECT   35   17                                                            
MASTER        0    0    0    0    0    0    0    0   35    0   74    0
END

RDKit          3D

35 37  0  0  0  0  0  0  0  0999 V2000
   -2.1297   -1.0320    4.6026 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7546    0.0604    3.6750 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4521    1.3701    4.0048 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1547    2.1015    2.8970 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2687    1.2545    1.8513 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6276   -0.0077    2.2606 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8286   -1.1242    1.2991 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2332   -0.7727   -0.0974 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.6316   -1.8218   -1.1682 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.0380   -3.2012   -0.8551 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1930   -1.3930   -2.5475 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8333   -0.1474   -2.8812 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9097    0.9651   -1.9025 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5024    2.0734   -2.2453 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5708    0.6994   -0.5495 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.0854    0.9355   -0.7313 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9975    1.7278    0.4753 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3753   -1.8249    4.5828 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2150   -0.6695    5.6320 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0934   -1.4646    4.3152 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4072    1.9120    4.9394 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3480   -2.0259    1.6946 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9012   -1.3348    1.2129 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1360   -0.8177    0.0079 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7232   -1.9327   -1.1899 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2777   -3.9223   -1.6452 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4422   -3.6067    0.0774 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0530   -3.1566   -0.7633 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1719   -2.1556   -3.3246 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5058    0.1149   -3.8808 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5173    0.2728   -1.4883 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2803    1.9606   -1.0691 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6426    0.7858    0.1985 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    2.7234    0.3184 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0889    1.8247    0.3522 H   0  0  0  0  0  0  0  0  0  0  0  0
  5 17  1  0
  5  6  2  0
  9  8  1  0
 15 13  1  0
 15  8  1  0
 12 11  2  0
  6  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  1  0
 12 13  1  0
  2  1  1  0
 11  9  1  0
 13 14  2  0
 15 17  1  0
  8 24  1  1
  8  7  1  0
  9 10  1  0
  7  6  1  0
 15 16  1  6
 12 30  1  0
 11 29  1  0
  9 25  1  6
  7 22  1  0
  7 23  1  0
 17 34  1  0
 17 35  1  0
  3 21  1  0
  1 18  1  0
  1 19  1  0
  1 20  1  0
 10 26  1  0
 10 27  1  0
 10 28  1  0
 16 31  1  0
 16 32  1  0
 16 33  1  0
M  END

View in JSmol View DFT Assignments 3D Conformers

Synonyms

Not Available

Chemical Formula

C₁₅H₁₈O₂

Average Mass

230.3070 Da

Monoisotopic Mass

230.13068 Da

IUPAC Name

(4aS,5R,8aR)-3,5,8a-trimethyl-4H,4aH,5H,8H,8aH,9H-naphtho[2,3-b]furan-8-one

Traditional Name

(4aS,5R,8aR)-3,5,8a-trimethyl-4H,4aH,5H,9H-naphtho[2,3-b]furan-8-one

CAS Registry Number

Not Available

SMILES

[H]C1=C(C2=C(O1)C([H])([H])[C@]1(C(=O)C([H])=C([H])[C@@]([H])(C([H])([H])[H])[C@]1([H])C2([H])[H])C([H])([H])[H])C([H])([H])[H]

InChI Identifier

InChI=1S/C15H18O2/c1-9-4-5-14(16)15(3)7-13-11(6-12(9)15)10(2)8-17-13/h4-5,8-9,12H,6-7H2,1-3H3/t9-,12+,15-/m1/s1

InChI Key

IDGRBNKTZISWPG-MURWCNHISA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 125 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 150 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 175 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 225 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 250 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, chcl3, 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
Siphonochilus aethiopicus	JEOL database	Holzafel, C. W., et al, Phytochemistry 59, 405 (2002)

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as eremophilane, 8,9-secoeremophilane and furoeremophilane sesquiterpenoids. These are sesquiterpenoids with a structure based either on the eremophilane skeleton, its 8,9-seco derivative, or the furoeremophilane skeleton. Eremophilanes have been shown to be derived from eudesmanes by migration of the methyl group at C-10 to C-5.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Sesquiterpenoids

Direct Parent

Eremophilane, 8,9-secoeremophilane and furoeremophilane sesquiterpenoids

Alternative Parents

Substituents

Furoeremophilane sesquiterpenoid
Naphthofuran
Benzofuran
Cyclohexenone
Heteroaromatic compound
Furan
Ketone
Oxacycle
Organoheterocyclic compound
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	3.44	ALOGPS
logP	3.76	ChemAxon
logS	-4	ALOGPS
pKa (Strongest Acidic)	18.85	ChemAxon
pKa (Strongest Basic)	-2.8	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	30.21 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	68.43 m³·mol⁻¹	ChemAxon
Polarizability	26.28 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

552298

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

636532

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Holzafel, C. W., et al. (2002). Holzafel, C. W., et al, Phytochemistry 59, 405 (2002). Phytochem..

Showing NP-Card for 4aalphaH-3,5alpha,8abeta-trimethyl-4,4a,8a,9-tetrahydronaphtho[2,3b]-fura+ (NP0028974)

MOL for NP0028974 (4aalphaH-3,5alpha,8abeta-trimethyl-4,4a,8a,9-tetrahydronaphtho[2,3b]-fura+)

3D MOL for NP0028974 (4aalphaH-3,5alpha,8abeta-trimethyl-4,4a,8a,9-tetrahydronaphtho[2,3b]-fura+)

3D SDF for NP0028974 (4aalphaH-3,5alpha,8abeta-trimethyl-4,4a,8a,9-tetrahydronaphtho[2,3b]-fura+)

3D-SDF for NP0028974 (4aalphaH-3,5alpha,8abeta-trimethyl-4,4a,8a,9-tetrahydronaphtho[2,3b]-fura+)

PDB for NP0028974 (4aalphaH-3,5alpha,8abeta-trimethyl-4,4a,8a,9-tetrahydronaphtho[2,3b]-fura+)

3D PDB for NP0028974 (4aalphaH-3,5alpha,8abeta-trimethyl-4,4a,8a,9-tetrahydronaphtho[2,3b]-fura+)

SMILES for NP0028974 (4aalphaH-3,5alpha,8abeta-trimethyl-4,4a,8a,9-tetrahydronaphtho[2,3b]-fura+)

INCHI for NP0028974 (4aalphaH-3,5alpha,8abeta-trimethyl-4,4a,8a,9-tetrahydronaphtho[2,3b]-fura+)

Structure for NP0028974 (4aalphaH-3,5alpha,8abeta-trimethyl-4,4a,8a,9-tetrahydronaphtho[2,3b]-fura+)

3D Structure for NP0028974 (4aalphaH-3,5alpha,8abeta-trimethyl-4,4a,8a,9-tetrahydronaphtho[2,3b]-fura+)