NP-MRD: Showing NP-Card for 1alpha-hydroxy-9-deoxycacalol (NP0033155)

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Record Information

Version

2.0

Created at

2021-06-19 23:46:43 UTC

Updated at

2021-06-30 00:02:46 UTC

NP-MRD ID

NP0033155

Secondary Accession Numbers

None

Natural Product Identification

Common Name

1alpha-hydroxy-9-deoxycacalol

Provided By

JEOL Database JEOL Logo

Description

1Alpha-hydroxy-9-deoxycacalol 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. 1alpha-hydroxy-9-deoxycacalol is found in Ligularia macrophylla. 1alpha-hydroxy-9-deoxycacalol was first documented in 2007 (PMID: 17672504). Based on a literature review very few articles have been published on 1alpha-hydroxy-9-deoxycacalol.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306202101463D          

 35 37  0  0  0  0            999 V2000
   -2.3698    2.0994    0.4933 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3631    1.0792    0.8739 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1375    1.3444    1.4514 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5577    0.2040    1.6612 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2160   -0.8193    1.2159 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1611   -2.1526    1.2498 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7422   -3.0948    0.7304 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9984   -2.6843    0.2113 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3765   -1.2959    0.2335 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7108   -0.8315   -0.2946 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4293   -0.3525    0.7288 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9236   -3.7362   -0.4112 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.8780   -3.6519   -1.9443 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6173   -5.1687    0.0583 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.1349   -5.4890   -0.0633 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.3259   -4.5511    0.8227 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.4565   -4.9951    2.1761 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7051    1.9501   -0.5376 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9537    3.1104    0.5608 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2364    2.0505    1.1596 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3622    2.2544    1.7539 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1220   -2.4432    1.6614 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6159   -0.5412   -1.3450 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0751    0.0278    0.2744 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4948   -1.5847   -0.2015 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9521   -3.5482   -0.0849 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5027   -4.4305   -2.3954 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8597   -3.7667   -2.3307 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2505   -2.6897   -2.3076 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9307   -5.2836    1.1044 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2033   -5.8925   -0.5206 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9662   -6.5305    0.2353 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8132   -5.3944   -1.1064 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7320   -4.6499    0.5518 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8819   -4.2841    2.6858 H   0  0  0  0  0  0  0  0  0  0  0  0
  9 11  2  0  0  0  0
  5  6  2  0  0  0  0
  5 11  1  0  0  0  0
 12  8  1  0  0  0  0
  7 16  1  0  0  0  0
  7  8  2  0  0  0  0
 15 14  1  0  0  0  0
 11  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
 15 16  1  0  0  0  0
  2  1  1  0  0  0  0
 14 12  1  0  0  0  0
 12 13  1  0  0  0  0
  7  6  1  0  0  0  0
 16 17  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 15 32  1  0  0  0  0
 15 33  1  0  0  0  0
 14 30  1  0  0  0  0
 14 31  1  0  0  0  0
 12 26  1  1  0  0  0
 16 34  1  6  0  0  0
  6 22  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
 13 27  1  0  0  0  0
 13 28  1  0  0  0  0
 13 29  1  0  0  0  0
 17 35  1  0  0  0  0
 10 23  1  0  0  0  0
 10 24  1  0  0  0  0
 10 25  1  0  0  0  0
M  END

     RDKit          3D

 35 37  0  0  0  0  0  0  0  0999 V2000
   -2.3698    2.0994    0.4933 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3631    1.0792    0.8739 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1375    1.3444    1.4514 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5577    0.2040    1.6612 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2160   -0.8193    1.2159 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1611   -2.1526    1.2498 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7422   -3.0948    0.7304 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9984   -2.6843    0.2113 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3765   -1.2959    0.2335 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7108   -0.8315   -0.2946 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4293   -0.3525    0.7288 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9236   -3.7362   -0.4112 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.8780   -3.6519   -1.9443 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6173   -5.1687    0.0583 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1349   -5.4890   -0.0633 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3259   -4.5511    0.8227 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.4565   -4.9951    2.1761 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7051    1.9501   -0.5376 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9537    3.1104    0.5608 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2364    2.0505    1.1596 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3622    2.2544    1.7539 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1220   -2.4432    1.6614 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6159   -0.5412   -1.3450 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0751    0.0278    0.2744 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4948   -1.5847   -0.2015 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9521   -3.5482   -0.0849 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5027   -4.4305   -2.3954 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8597   -3.7667   -2.3307 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2505   -2.6897   -2.3076 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9307   -5.2836    1.1044 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2033   -5.8925   -0.5206 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9662   -6.5305    0.2353 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8132   -5.3944   -1.1064 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7320   -4.6499    0.5518 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8819   -4.2841    2.6858 H   0  0  0  0  0  0  0  0  0  0  0  0
  9 11  2  0
  5  6  2  0
  5 11  1  0
 12  8  1  0
  7 16  1  0
  7  8  2  0
 15 14  1  0
 11  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  1  0
 15 16  1  0
  2  1  1  0
 14 12  1  0
 12 13  1  0
  7  6  1  0
 16 17  1  0
  8  9  1  0
  9 10  1  0
 15 32  1  0
 15 33  1  0
 14 30  1  0
 14 31  1  0
 12 26  1  1
 16 34  1  6
  6 22  1  0
  3 21  1  0
  1 18  1  0
  1 19  1  0
  1 20  1  0
 13 27  1  0
 13 28  1  0
 13 29  1  0
 17 35  1  0
 10 23  1  0
 10 24  1  0
 10 25  1  0
M  END


  Mrv1652306202101463D          

 35 37  0  0  0  0            999 V2000
   -2.3698    2.0994    0.4933 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3631    1.0792    0.8739 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1375    1.3444    1.4514 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5577    0.2040    1.6612 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2160   -0.8193    1.2159 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1611   -2.1526    1.2498 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7422   -3.0948    0.7304 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9984   -2.6843    0.2113 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3765   -1.2959    0.2335 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7108   -0.8315   -0.2946 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4293   -0.3525    0.7288 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9236   -3.7362   -0.4112 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.8780   -3.6519   -1.9443 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6173   -5.1687    0.0583 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.1349   -5.4890   -0.0633 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.3259   -4.5511    0.8227 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.4565   -4.9951    2.1761 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7051    1.9501   -0.5376 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9537    3.1104    0.5608 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2364    2.0505    1.1596 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3622    2.2544    1.7539 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1220   -2.4432    1.6614 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6159   -0.5412   -1.3450 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0751    0.0278    0.2744 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4948   -1.5847   -0.2015 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9521   -3.5482   -0.0849 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5027   -4.4305   -2.3954 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8597   -3.7667   -2.3307 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2505   -2.6897   -2.3076 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9307   -5.2836    1.1044 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2033   -5.8925   -0.5206 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9662   -6.5305    0.2353 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8132   -5.3944   -1.1064 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7320   -4.6499    0.5518 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8819   -4.2841    2.6858 H   0  0  0  0  0  0  0  0  0  0  0  0
  9 11  2  0  0  0  0
  5  6  2  0  0  0  0
  5 11  1  0  0  0  0
 12  8  1  0  0  0  0
  7 16  1  0  0  0  0
  7  8  2  0  0  0  0
 15 14  1  0  0  0  0
 11  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
 15 16  1  0  0  0  0
  2  1  1  0  0  0  0
 14 12  1  0  0  0  0
 12 13  1  0  0  0  0
  7  6  1  0  0  0  0
 16 17  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 15 32  1  0  0  0  0
 15 33  1  0  0  0  0
 14 30  1  0  0  0  0
 14 31  1  0  0  0  0
 12 26  1  1  0  0  0
 16 34  1  6  0  0  0
  6 22  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
 13 27  1  0  0  0  0
 13 28  1  0  0  0  0
 13 29  1  0  0  0  0
 17 35  1  0  0  0  0
 10 23  1  0  0  0  0
 10 24  1  0  0  0  0
 10 25  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0033155

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]O[C@]1([H])C2=C(C(=C3C(OC([H])=C3C([H])([H])[H])=C2[H])C([H])([H])[H])[C@@]([H])(C([H])([H])[H])C([H])([H])C1([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C15H18O2/c1-8-4-5-12(16)11-6-13-15(9(2)7-17-13)10(3)14(8)11/h6-8,12,16H,4-5H2,1-3H3/t8-,12-/m0/s1

> <INCHI_KEY>
ZRWPAGVTPFFNTL-UFBFGSQYSA-N

> <FORMULA>
C15H18O2

> <MOLECULAR_WEIGHT>
230.307

> <EXACT_MASS>
230.13067982

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_ATOM_COUNT>
35

> <JCHEM_AVERAGE_POLARIZABILITY>
26.414633121368013

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(5S,8S)-3,4,5-trimethyl-5H,6H,7H,8H-naphtho[2,3-b]furan-8-ol

> <ALOGPS_LOGP>
3.84

> <JCHEM_LOGP>
3.6676742306666665

> <ALOGPS_LOGS>
-3.85

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.328160201401772

> <JCHEM_PKA_STRONGEST_BASIC>
-2.775758708841904

> <JCHEM_POLAR_SURFACE_AREA>
33.370000000000005

> <JCHEM_REFRACTIVITY>
68.5278

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.24e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(5S,8S)-3,4,5-trimethyl-5H,6H,7H,8H-naphtho[2,3-b]furan-8-ol

> <JCHEM_VEBER_RULE>
1

$$$$

     RDKit          3D

 35 37  0  0  0  0  0  0  0  0999 V2000
   -2.3698    2.0994    0.4933 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3631    1.0792    0.8739 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1375    1.3444    1.4514 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5577    0.2040    1.6612 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2160   -0.8193    1.2159 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1611   -2.1526    1.2498 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7422   -3.0948    0.7304 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9984   -2.6843    0.2113 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3765   -1.2959    0.2335 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7108   -0.8315   -0.2946 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4293   -0.3525    0.7288 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9236   -3.7362   -0.4112 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.8780   -3.6519   -1.9443 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6173   -5.1687    0.0583 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1349   -5.4890   -0.0633 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3259   -4.5511    0.8227 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.4565   -4.9951    2.1761 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7051    1.9501   -0.5376 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9537    3.1104    0.5608 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2364    2.0505    1.1596 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3622    2.2544    1.7539 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1220   -2.4432    1.6614 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6159   -0.5412   -1.3450 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0751    0.0278    0.2744 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4948   -1.5847   -0.2015 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9521   -3.5482   -0.0849 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5027   -4.4305   -2.3954 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8597   -3.7667   -2.3307 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2505   -2.6897   -2.3076 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9307   -5.2836    1.1044 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2033   -5.8925   -0.5206 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9662   -6.5305    0.2353 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8132   -5.3944   -1.1064 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7320   -4.6499    0.5518 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8819   -4.2841    2.6858 H   0  0  0  0  0  0  0  0  0  0  0  0
  9 11  2  0
  5  6  2  0
  5 11  1  0
 12  8  1  0
  7 16  1  0
  7  8  2  0
 15 14  1  0
 11  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  1  0
 15 16  1  0
  2  1  1  0
 14 12  1  0
 12 13  1  0
  7  6  1  0
 16 17  1  0
  8  9  1  0
  9 10  1  0
 15 32  1  0
 15 33  1  0
 14 30  1  0
 14 31  1  0
 12 26  1  1
 16 34  1  6
  6 22  1  0
  3 21  1  0
  1 18  1  0
  1 19  1  0
  1 20  1  0
 13 27  1  0
 13 28  1  0
 13 29  1  0
 17 35  1  0
 10 23  1  0
 10 24  1  0
 10 25  1  0
M  END

HEADER    PROTEIN                                 20-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   20-JUN-21         0                                  
HETATM    1  C   UNK     0      -2.370   2.099   0.493  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.363   1.079   0.874  0.00  0.00           C+0
HETATM    3  C   UNK     0      -0.138   1.344   1.451  0.00  0.00           C+0
HETATM    4  O   UNK     0       0.558   0.204   1.661  0.00  0.00           O+0
HETATM    5  C   UNK     0      -0.216  -0.819   1.216  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.161  -2.153   1.250  0.00  0.00           C+0
HETATM    7  C   UNK     0      -0.742  -3.095   0.730  0.00  0.00           C+0
HETATM    8  C   UNK     0      -1.998  -2.684   0.211  0.00  0.00           C+0
HETATM    9  C   UNK     0      -2.377  -1.296   0.234  0.00  0.00           C+0
HETATM   10  C   UNK     0      -3.711  -0.832  -0.295  0.00  0.00           C+0
HETATM   11  C   UNK     0      -1.429  -0.353   0.729  0.00  0.00           C+0
HETATM   12  C   UNK     0      -2.924  -3.736  -0.411  0.00  0.00           C+0
HETATM   13  C   UNK     0      -2.878  -3.652  -1.944  0.00  0.00           C+0
HETATM   14  C   UNK     0      -2.617  -5.169   0.058  0.00  0.00           C+0
HETATM   15  C   UNK     0      -1.135  -5.489  -0.063  0.00  0.00           C+0
HETATM   16  C   UNK     0      -0.326  -4.551   0.823  0.00  0.00           C+0
HETATM   17  O   UNK     0      -0.457  -4.995   2.176  0.00  0.00           O+0
HETATM   18  H   UNK     0      -2.705   1.950  -0.538  0.00  0.00           H+0
HETATM   19  H   UNK     0      -1.954   3.110   0.561  0.00  0.00           H+0
HETATM   20  H   UNK     0      -3.236   2.050   1.160  0.00  0.00           H+0
HETATM   21  H   UNK     0       0.362   2.254   1.754  0.00  0.00           H+0
HETATM   22  H   UNK     0       1.122  -2.443   1.661  0.00  0.00           H+0
HETATM   23  H   UNK     0      -3.616  -0.541  -1.345  0.00  0.00           H+0
HETATM   24  H   UNK     0      -4.075   0.028   0.274  0.00  0.00           H+0
HETATM   25  H   UNK     0      -4.495  -1.585  -0.202  0.00  0.00           H+0
HETATM   26  H   UNK     0      -3.952  -3.548  -0.085  0.00  0.00           H+0
HETATM   27  H   UNK     0      -3.503  -4.431  -2.395  0.00  0.00           H+0
HETATM   28  H   UNK     0      -1.860  -3.767  -2.331  0.00  0.00           H+0
HETATM   29  H   UNK     0      -3.251  -2.690  -2.308  0.00  0.00           H+0
HETATM   30  H   UNK     0      -2.931  -5.284   1.104  0.00  0.00           H+0
HETATM   31  H   UNK     0      -3.203  -5.893  -0.521  0.00  0.00           H+0
HETATM   32  H   UNK     0      -0.966  -6.531   0.235  0.00  0.00           H+0
HETATM   33  H   UNK     0      -0.813  -5.394  -1.106  0.00  0.00           H+0
HETATM   34  H   UNK     0       0.732  -4.650   0.552  0.00  0.00           H+0
HETATM   35  H   UNK     0      -0.882  -4.284   2.686  0.00  0.00           H+0
CONECT    1    2   18   19   20                                             
CONECT    2   11    3    1                                                  
CONECT    3    2    4   21                                                  
CONECT    4    3    5                                                       
CONECT    5    6   11    4                                                  
CONECT    6    5    7   22                                                  
CONECT    7   16    8    6                                                  
CONECT    8   12    7    9                                                  
CONECT    9   11    8   10                                                  
CONECT   10    9   23   24   25                                             
CONECT   11    9    5    2                                                  
CONECT   12    8   14   13   26                                             
CONECT   13   12   27   28   29                                             
CONECT   14   15   12   30   31                                             
CONECT   15   14   16   32   33                                             
CONECT   16    7   15   17   34                                             
CONECT   17   16   35                                                       
CONECT   18    1                                                            
CONECT   19    1                                                            
CONECT   20    1                                                            
CONECT   21    3                                                            
CONECT   22    6                                                            
CONECT   23   10                                                            
CONECT   24   10                                                            
CONECT   25   10                                                            
CONECT   26   12                                                            
CONECT   27   13                                                            
CONECT   28   13                                                            
CONECT   29   13                                                            
CONECT   30   14                                                            
CONECT   31   14                                                            
CONECT   32   15                                                            
CONECT   33   15                                                            
CONECT   34   16                                                            
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
   -2.3698    2.0994    0.4933 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3631    1.0792    0.8739 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1375    1.3444    1.4514 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5577    0.2040    1.6612 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2160   -0.8193    1.2159 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1611   -2.1526    1.2498 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7422   -3.0948    0.7304 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9984   -2.6843    0.2113 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3765   -1.2959    0.2335 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7108   -0.8315   -0.2946 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4293   -0.3525    0.7288 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9236   -3.7362   -0.4112 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.8780   -3.6519   -1.9443 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6173   -5.1687    0.0583 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1349   -5.4890   -0.0633 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3259   -4.5511    0.8227 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.4565   -4.9951    2.1761 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7051    1.9501   -0.5376 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9537    3.1104    0.5608 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2364    2.0505    1.1596 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3622    2.2544    1.7539 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1220   -2.4432    1.6614 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6159   -0.5412   -1.3450 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0751    0.0278    0.2744 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4948   -1.5847   -0.2015 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9521   -3.5482   -0.0849 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5027   -4.4305   -2.3954 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8597   -3.7667   -2.3307 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2505   -2.6897   -2.3076 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9307   -5.2836    1.1044 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2033   -5.8925   -0.5206 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9662   -6.5305    0.2353 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8132   -5.3944   -1.1064 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7320   -4.6499    0.5518 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8819   -4.2841    2.6858 H   0  0  0  0  0  0  0  0  0  0  0  0
  9 11  2  0
  5  6  2  0
  5 11  1  0
 12  8  1  0
  7 16  1  0
  7  8  2  0
 15 14  1  0
 11  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  1  0
 15 16  1  0
  2  1  1  0
 14 12  1  0
 12 13  1  0
  7  6  1  0
 16 17  1  0
  8  9  1  0
  9 10  1  0
 15 32  1  0
 15 33  1  0
 14 30  1  0
 14 31  1  0
 12 26  1  1
 16 34  1  6
  6 22  1  0
  3 21  1  0
  1 18  1  0
  1 19  1  0
  1 20  1  0
 13 27  1  0
 13 28  1  0
 13 29  1  0
 17 35  1  0
 10 23  1  0
 10 24  1  0
 10 25  1  0
M  END

View in JSmol View DFT Assignments 3D Conformers

Synonyms

Value	Source
1a-Hydroxy-9-deoxycacalol	Generator
1Α-hydroxy-9-deoxycacalol	Generator

Chemical Formula

C₁₅H₁₈O₂

Average Mass

230.3070 Da

Monoisotopic Mass

230.13068 Da

IUPAC Name

(5S,8S)-3,4,5-trimethyl-5H,6H,7H,8H-naphtho[2,3-b]furan-8-ol

Traditional Name

(5S,8S)-3,4,5-trimethyl-5H,6H,7H,8H-naphtho[2,3-b]furan-8-ol

CAS Registry Number

Not Available

SMILES

[H]O[C@]1([H])C2=C(C(=C3C(OC([H])=C3C([H])([H])[H])=C2[H])C([H])([H])[H])[C@@]([H])(C([H])([H])[H])C([H])([H])C1([H])[H]

InChI Identifier

InChI=1S/C15H18O2/c1-8-4-5-12(16)11-6-13-15(9(2)7-17-13)10(3)14(8)11/h6-8,12,16H,4-5H2,1-3H3/t8-,12-/m0/s1

InChI Key

ZRWPAGVTPFFNTL-UFBFGSQYSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
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, 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, 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, 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
Ligularia macrophylla	JEOL database	Wang, Q., et al, J. Nat. Prod. 70, 1259 (2007)

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
Tetralin
Benzofuran
Benzenoid
Heteroaromatic compound
Furan
Secondary alcohol
Oxacycle
Organoheterocyclic compound
Organic oxygen compound
Hydrocarbon derivative
Organooxygen compound
Alcohol
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	3.84	ALOGPS
logP	3.67	ChemAxon
logS	-3.8	ALOGPS
pKa (Strongest Acidic)	14.33	ChemAxon
pKa (Strongest Basic)	-2.8	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	33.37 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	68.53 m³·mol⁻¹	ChemAxon
Polarizability	26.41 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

23311477

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

23627125

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Wang Q, Mu Q, Shibano M, Morris-Natschke SL, Lee KH, Chen DF: Eremophilane sesquiterpenes from Ligularia macrophylla. J Nat Prod. 2007 Aug;70(8):1259-62. doi: 10.1021/np070113x. Epub 2007 Aug 2. [PubMed:17672504 ]
Wang, Q., et al. (2007). Wang, Q., et al, J. Nat. Prod. 70, 1259 (2007). J. Nat. Prod..

Showing NP-Card for 1alpha-hydroxy-9-deoxycacalol (NP0033155)

MOL for NP0033155 (1alpha-hydroxy-9-deoxycacalol)

3D MOL for NP0033155 (1alpha-hydroxy-9-deoxycacalol)

3D SDF for NP0033155 (1alpha-hydroxy-9-deoxycacalol)

3D-SDF for NP0033155 (1alpha-hydroxy-9-deoxycacalol)

PDB for NP0033155 (1alpha-hydroxy-9-deoxycacalol)

3D PDB for NP0033155 (1alpha-hydroxy-9-deoxycacalol)

SMILES for NP0033155 (1alpha-hydroxy-9-deoxycacalol)

INCHI for NP0033155 (1alpha-hydroxy-9-deoxycacalol)

Structure for NP0033155 (1alpha-hydroxy-9-deoxycacalol)

3D Structure for NP0033155 (1alpha-hydroxy-9-deoxycacalol)