NP-MRD: Showing NP-Card for Marrubenol (NP0065181)

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Record Information

Version

2.0

Created at

2022-04-28 09:26:17 UTC

Updated at

2022-04-28 09:26:17 UTC

NP-MRD ID

NP0065181

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Marrubenol

Description

Marrubenol belongs to the class of organic compounds known as colensane and clerodane diterpenoids. These are diterpenoids with a structure based on the clerodane or the colensane skeleton. Clerodanes arise from labdanes by two methyl migrations. Marrubenol is found in Marrubium vulgare . Marrubenol was first documented in 2003 (PMID: 14597602). Based on a literature review a significant number of articles have been published on marrubenol (PMID: 18221123) (PMID: 30003743) (PMID: 23899837) (PMID: 15178374) (PMID: 12567286).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 56 58  0  0  0  0  0  0  0  0999 V2000
    0.7306    2.0280    2.0882 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5934    1.7444    0.5804 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.5919    2.4552    0.0495 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7918    1.6453   -0.2704 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.0402    1.6456   -1.6426 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6772    0.1962    0.1580 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.8938   -0.6100   -0.0017 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.3424   -1.2732    1.3144 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1431    0.1579   -0.4563 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1899   -0.7970   -0.5419 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7866   -1.7365   -1.0078 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5251   -2.4978   -0.9346 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4021   -1.8390   -0.2023 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4054   -0.3425   -0.4113 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.1718   -0.0181   -1.8592 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7275    0.2917    0.3727 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.7127   -0.4282    1.5998 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0775   -0.0455   -0.2658 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2442    0.3814    0.5759 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5448    0.0261   -0.0711 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2351   -1.1554    0.0983 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3825   -1.0802   -0.6732 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3933    0.0727   -1.2755 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3160    0.7631   -0.9441 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7465    1.9532    2.4522 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4478    3.1191    2.1820 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0213    1.4922    2.6848 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5210    2.2354    0.1535 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3089    3.0280   -0.8678 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8467    3.2779    0.7794 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6581    2.0590    0.2830 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6167    2.4265   -1.8385 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5010    0.2681    1.2787 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9980   -2.1264    1.0460 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8832   -0.5203    1.9226 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5094   -1.6529    1.8995 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4695    0.8996    0.2596 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0522    0.5120   -1.5060 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5614   -0.9947    0.3575 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0534   -1.3665   -2.0387 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6310   -2.4496   -0.7696 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6666   -3.5235   -0.4837 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1921   -2.7203   -1.9911 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5410   -2.3206   -0.5979 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3774   -2.0665    0.8894 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1691    1.0024   -2.0529 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6812   -0.6842   -2.1871 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9959   -0.2445   -2.5296 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2793   -0.0233    2.2725 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1449   -1.0806   -0.6041 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1532    0.5714   -1.2140 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2069   -0.0454    1.6096 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2974    1.4814    0.7154 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9547   -1.9949    0.7108 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1656   -1.8452   -0.7782 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0376    1.7489   -1.2754 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  4  6  1  0
  6  7  1  0
  7  8  1  1
  7  9  1  0
  9 10  1  0
  7 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  6
 14 16  1  0
 16 17  1  1
 16 18  1  0
 18 19  1  0
 19 20  1  0
 20 24  2  0
 24 23  1  0
 23 22  1  0
 22 21  2  0
 16  2  1  0
 21 20  1  0
 14  6  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
  2 28  1  6
  3 29  1  0
  3 30  1  0
  4 31  1  1
  5 32  1  0
  6 33  1  1
  8 34  1  0
  8 35  1  0
  8 36  1  0
  9 37  1  0
  9 38  1  0
 10 39  1  0
 11 40  1  0
 11 41  1  0
 12 42  1  0
 12 43  1  0
 13 44  1  0
 13 45  1  0
 15 46  1  0
 15 47  1  0
 15 48  1  0
 17 49  1  0
 18 50  1  0
 18 51  1  0
 19 52  1  0
 19 53  1  0
 24 56  1  0
 22 55  1  0
 21 54  1  0
M  END


  Mrv1652304282211262D          

 24 26  0  0  1  0            999 V2000
   -0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.6500    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0000   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -0.0000    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4289   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0416    0.7284    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4788    1.4281    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0915    2.1565    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2745    2.2713    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1313    3.0838    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8597    3.4711    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4532    2.8980    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8163    0.7284    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3873   -2.3784    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3873   -2.3784    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0499   -3.0781    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  4  3  1  1  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  1  6  1  0  0  0  0
  5  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  4 10  1  0  0  0  0
 10 11  1  1  0  0  0
  8 12  1  6  0  0  0
  7 13  1  1  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 15 19  2  0  0  0  0
  7 20  1  6  0  0  0
  5 21  1  1  0  0  0
  3 22  1  6  0  0  0
  3 23  1  1  0  0  0
 23 24  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0065181

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@@H]1C[C@@H](O)[C@H]2[C@@](C)(CO)CCC[C@]2(C)[C@@]1(O)CCC1=COC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C20H32O4/c1-14-11-16(22)17-18(2,13-21)7-4-8-19(17,3)20(14,23)9-5-15-6-10-24-12-15/h6,10,12,14,16-17,21-23H,4-5,7-9,11,13H2,1-3H3/t14-,16-,17+,18-,19+,20-/m1/s1

> <INCHI_KEY>
NZMHIKFTAXRIDL-FQFOHHTNSA-N

> <FORMULA>
C20H32O4

> <MOLECULAR_WEIGHT>
336.472

> <EXACT_MASS>
336.23005951

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
56

> <JCHEM_AVERAGE_POLARIZABILITY>
38.159438809740564

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1R,2R,4R,4aS,5S,8aS)-1-[2-(furan-3-yl)ethyl]-5-(hydroxymethyl)-2,5,8a-trimethyl-decahydronaphthalene-1,4-diol

> <ALOGPS_LOGP>
2.69

> <JCHEM_LOGP>
2.620317973333333

> <ALOGPS_LOGS>
-3.69

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.779102156790646

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.056155894356099

> <JCHEM_PKA_STRONGEST_BASIC>
-2.753048832200534

> <JCHEM_POLAR_SURFACE_AREA>
73.83000000000001

> <JCHEM_REFRACTIVITY>
93.3277

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.82e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1R,2R,4R,4aS,5S,8aS)-1-[2-(furan-3-yl)ethyl]-5-(hydroxymethyl)-2,5,8a-trimethyl-hexahydro-2H-naphthalene-1,4-diol

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 28-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   28-APR-22         0                                  
HETATM    1  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.000  -3.080   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.000  -0.000   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.667  -0.000   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       2.667  -4.620   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       5.335  -0.000   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.944   1.360   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.760   2.666   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       2.037   4.025   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       0.512   4.240   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       0.245   5.756   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       1.605   6.479   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       2.713   5.410   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       3.390   1.360   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       1.334   0.770   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -0.723  -4.440   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       0.723  -4.440   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0      -0.093  -5.746   0.000  0.00  0.00           O+0
CONECT    1    2    6                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4   22   23                                             
CONECT    4    3    5   10                                                  
CONECT    5    4    6    7   21                                             
CONECT    6    5    1                                                       
CONECT    7    5    8   13   20                                             
CONECT    8    7    9   12                                                  
CONECT    9    8   10                                                       
CONECT   10    9    4   11                                                  
CONECT   11   10                                                            
CONECT   12    8                                                            
CONECT   13    7   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16   19                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   15                                                       
CONECT   20    7                                                            
CONECT   21    5                                                            
CONECT   22    3                                                            
CONECT   23    3   24                                                       
CONECT   24   23                                                            
MASTER        0    0    0    0    0    0    0    0   24    0   52    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₀H₃₂O₄

Average Mass

336.4720 Da

Monoisotopic Mass

336.23006 Da

IUPAC Name

(1R,2R,4R,4aS,5S,8aS)-1-[2-(furan-3-yl)ethyl]-5-(hydroxymethyl)-2,5,8a-trimethyl-decahydronaphthalene-1,4-diol

Traditional Name

(1R,2R,4R,4aS,5S,8aS)-1-[2-(furan-3-yl)ethyl]-5-(hydroxymethyl)-2,5,8a-trimethyl-hexahydro-2H-naphthalene-1,4-diol

CAS Registry Number

Not Available

SMILES

C[C@@H]1C[C@@H](O)[C@H]2[C@@](C)(CO)CCC[C@]2(C)[C@@]1(O)CCC1=COC=C1

InChI Identifier

InChI=1S/C20H32O4/c1-14-11-16(22)17-18(2,13-21)7-4-8-19(17,3)20(14,23)9-5-15-6-10-24-12-15/h6,10,12,14,16-17,21-23H,4-5,7-9,11,13H2,1-3H3/t14-,16-,17+,18-,19+,20-/m1/s1

InChI Key

NZMHIKFTAXRIDL-FQFOHHTNSA-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
Marrubium vulgare	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as colensane and clerodane diterpenoids. These are diterpenoids with a structure based on the clerodane or the colensane skeleton. Clerodanes arise from labdanes by two methyl migrations.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Diterpenoids

Direct Parent

Colensane and clerodane diterpenoids

Alternative Parents

Substituents

Clerodane diterpenoid
Heteroaromatic compound
Tertiary alcohol
Furan
Cyclic alcohol
Secondary alcohol
Oxacycle
Organoheterocyclic compound
Organic oxygen compound
Hydrocarbon derivative
Primary alcohol
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	2.69	ALOGPS
logP	2.62	ChemAxon
logS	-3.7	ALOGPS
pKa (Strongest Acidic)	14.06	ChemAxon
pKa (Strongest Basic)	-2.8	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	73.83 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	93.33 m³·mol⁻¹	ChemAxon
Polarizability	38.16 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

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00022294

Chemspider ID

8625106

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

10449689

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Tirapelli CR, Ambrosio SR, da Costa FB, de Oliveira AM: Diterpenes: a therapeutic promise for cardiovascular diseases. Recent Pat Cardiovasc Drug Discov. 2008 Jan;3(1):1-8. doi: 10.2174/157489008783331689. [PubMed:18221123 ]
Zhang Y, Ma R, Cheng S, Gu G: Marrubenol inhibits osteosarcoma cancer cell growth by inducing autophagic cell death and inhibiting cancer cell migration and invasion. J BUON. 2018 May-Jun;23(3):729-734. [PubMed:30003743 ]
Popoola OK, Elbagory AM, Ameer F, Hussein AA: Marrubiin. Molecules. 2013 Jul 29;18(8):9049-60. doi: 10.3390/molecules18089049. [PubMed:23899837 ]
El Bardai S, Hamaide MC, Lyoussi B, Quetin-Leclercq J, Morel N, Wibo M: Marrubenol interacts with the phenylalkylamine binding site of the L-type calcium channel. Eur J Pharmacol. 2004 May 25;492(2-3):269-72. doi: 10.1016/j.ejphar.2004.04.007. [PubMed:15178374 ]
El-Bardai S, Wibo M, Hamaide MC, Lyoussi B, Quetin-Leclercq J, Morel N: Characterisation of marrubenol, a diterpene extracted from Marrubium vulgare, as an L-type calcium channel blocker. Br J Pharmacol. 2003 Dec;140(7):1211-6. doi: 10.1038/sj.bjp.0705561. Epub 2003 Nov 3. [PubMed:14597602 ]
El Bardai S, Morel N, Wibo M, Fabre N, Llabres G, Lyoussi B, Quetin-Leclercq J: The vasorelaxant activity of marrubenol and marrubiin from Marrubium vulgare. Planta Med. 2003 Jan;69(1):75-7. doi: 10.1055/s-2003-37042. [PubMed:12567286 ]

Showing NP-Card for Marrubenol (NP0065181)

MOL for NP0065181 (Marrubenol)

3D MOL for NP0065181 (Marrubenol)

3D SDF for NP0065181 (Marrubenol)

3D-SDF for NP0065181 (Marrubenol)

PDB for NP0065181 (Marrubenol)

3D PDB for NP0065181 (Marrubenol)

SMILES for NP0065181 (Marrubenol)

INCHI for NP0065181 (Marrubenol)

Structure for NP0065181 (Marrubenol)

3D Structure for NP0065181 (Marrubenol)