NP-MRD: Showing NP-Card for (3r,3as,4s,8as)-3-hydroxy-3-isopropyl-6,8a-dimethyl-1,2,3a,4,5,8-hexahydroazulen-4-yl 4-hydroxybenzoate (NP0149718)

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Record Information

Version

2.0

Created at

2022-09-02 05:38:53 UTC

Updated at

2022-09-02 05:38:53 UTC

NP-MRD ID

NP0149718

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(3r,3as,4s,8as)-3-hydroxy-3-isopropyl-6,8a-dimethyl-1,2,3a,4,5,8-hexahydroazulen-4-yl 4-hydroxybenzoate

Description

Ferutinin belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units. (3r,3as,4s,8as)-3-hydroxy-3-isopropyl-6,8a-dimethyl-1,2,3a,4,5,8-hexahydroazulen-4-yl 4-hydroxybenzoate is found in Ferula elaeochytris, Ferula hermonis, Ferula jaeschkeana, Ferula kuhistanica, Ferula ovina and Ferula tenuisecta. (3r,3as,4s,8as)-3-hydroxy-3-isopropyl-6,8a-dimethyl-1,2,3a,4,5,8-hexahydroazulen-4-yl 4-hydroxybenzoate was first documented in 2019 (PMID: 32454752). Based on a literature review a significant number of articles have been published on Ferutinin (PMID: 32298751) (PMID: 35895028) (PMID: 35893609) (PMID: 35552354) (PMID: 35114339) (PMID: 35041680).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309022207382D          

 26 28  0  0  1  0            999 V2000
    4.3735    1.8011    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5485    1.8011    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1906    1.0578    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3863    0.8742    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7413    1.3886    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.5940    0.5769    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9566    1.1337    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4717    1.8011    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9566    2.4686    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.2922    3.2222    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2422    2.8811    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4723    2.4686    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2422    3.7061    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7413    2.2136    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.3863    2.7280    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.2027    3.5323    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4143    3.7755    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8096    3.2143    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2308    4.5798    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4424    4.8230    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2588    5.6273    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8636    6.1884    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6800    6.9927    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6520    5.9453    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8355    5.1409    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1906    2.5444    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  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
  5  6  1  1  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  6  0  0  0
  9 11  1  1  0  0  0
 11 12  1  0  0  0  0
 11 13  1  0  0  0  0
 14  9  1  6  0  0  0
  5 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  1  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 17 19  1  0  0  0  0
 19 20  2  0  0  0  0
 20 21  1  0  0  0  0
 21 22  2  0  0  0  0
 22 23  1  0  0  0  0
 22 24  1  0  0  0  0
 24 25  2  0  0  0  0
 19 25  1  0  0  0  0
 15 26  1  0  0  0  0
  2 26  1  0  0  0  0
M  END

     RDKit          3D

 56 58  0  0  0  0  0  0  0  0999 V2000
    0.1288   -3.7638   -1.3317 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6513   -2.6562   -0.7220 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1463   -2.9487    0.4717 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9695   -2.0292    1.3171 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3521   -0.7219    1.5430 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.0628   -0.9209    2.3320 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2841    0.0732    2.4719 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9328    1.1120    1.6002 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4628    0.8345    0.1860 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.3754   -0.0788   -0.3637 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4593    2.0419   -0.6678 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5829    3.1585   -0.3100 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9066    2.5619   -0.6950 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1253    0.2087    0.4509 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.3566   -0.1888   -0.7338 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.0127   -0.3276   -0.3986 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0004    0.4988   -0.9562 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5785    1.3619   -1.7673 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3955    0.3800   -0.6342 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8905   -0.5517    0.2476 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2438   -0.6236    0.5226 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1299    0.2295   -0.0740 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5015    0.1714    0.1920 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6172    1.1698   -0.9660 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2859    1.2415   -1.2374 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7893   -1.4040   -1.4704 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8463   -4.2190   -0.6148 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7064   -3.4097   -2.2063 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5968   -4.5171   -1.7191 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9394   -3.9443    0.8783 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9779   -2.0219    0.8646 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0866   -2.5375    2.2979 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4071   -1.8530    1.9588 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3409   -1.1216    3.3987 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6067   -0.0437    2.2375 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0808   -0.5606    2.8865 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7420    0.5188    3.3122 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4922    2.1055    1.8962 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0295    1.1401    1.6891 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6412    0.1805   -1.2581 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2532    1.7286   -1.7163 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6688    2.9465    0.2323 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2683    3.7370   -1.2308 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1323    3.9369    0.3011 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9582    3.3451    0.1105 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0746    3.0542   -1.6720 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6312    1.7809   -0.4736 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5225    1.0437    0.9389 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4301    0.6594   -1.4770 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2202   -1.2447    0.7400 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6244   -1.3689    1.2256 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.8350    0.7369    0.9542 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3343    1.8426   -1.4336 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9205    1.9976   -1.9473 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8220   -1.2538   -1.8805 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1400   -1.4866   -2.3821 H   0  0  0  0  0  0  0  0  0  0  0  0
 12 11  1  0
 11 13  1  0
 11  9  1  0
  9 10  1  6
  9  8  1  0
  8  7  1  0
  7  5  1  0
  5  6  1  1
  5  4  1  0
  4  3  1  0
  3  2  2  0
  2  1  1  0
  2 26  1  0
 26 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  2  0
 17 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 22 23  1  0
 22 24  1  0
 24 25  2  0
 15 14  1  0
 14  9  1  0
 14  5  1  0
 25 19  1  0
 12 42  1  0
 12 43  1  0
 12 44  1  0
 11 41  1  0
 13 45  1  0
 13 46  1  0
 13 47  1  0
 10 40  1  0
  8 38  1  0
  8 39  1  0
  7 36  1  0
  7 37  1  0
  6 33  1  0
  6 34  1  0
  6 35  1  0
  4 31  1  0
  4 32  1  0
  3 30  1  0
  1 27  1  0
  1 28  1  0
  1 29  1  0
 26 55  1  0
 26 56  1  0
 15 49  1  6
 20 50  1  0
 21 51  1  0
 23 52  1  0
 24 53  1  0
 25 54  1  0
 14 48  1  1
M  END


  Mrv1652309022207382D          

 26 28  0  0  1  0            999 V2000
    4.3735    1.8011    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5485    1.8011    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1906    1.0578    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3863    0.8742    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7413    1.3886    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.5940    0.5769    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9566    1.1337    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4717    1.8011    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9566    2.4686    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.2922    3.2222    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2422    2.8811    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4723    2.4686    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2422    3.7061    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7413    2.2136    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.3863    2.7280    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.2027    3.5323    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4143    3.7755    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8096    3.2143    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2308    4.5798    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4424    4.8230    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2588    5.6273    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8636    6.1884    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6800    6.9927    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6520    5.9453    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8355    5.1409    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1906    2.5444    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  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
  5  6  1  1  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  6  0  0  0
  9 11  1  1  0  0  0
 11 12  1  0  0  0  0
 11 13  1  0  0  0  0
 14  9  1  6  0  0  0
  5 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  1  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 17 19  1  0  0  0  0
 19 20  2  0  0  0  0
 20 21  1  0  0  0  0
 21 22  2  0  0  0  0
 22 23  1  0  0  0  0
 22 24  1  0  0  0  0
 24 25  2  0  0  0  0
 19 25  1  0  0  0  0
 15 26  1  0  0  0  0
  2 26  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0149718

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)[C@]1(O)CC[C@@]2(C)CC=C(C)C[C@H](OC(=O)C3=CC=C(O)C=C3)[C@@H]12

> <INCHI_IDENTIFIER>
InChI=1S/C22H30O4/c1-14(2)22(25)12-11-21(4)10-9-15(3)13-18(19(21)22)26-20(24)16-5-7-17(23)8-6-16/h5-9,14,18-19,23,25H,10-13H2,1-4H3/t18-,19+,21+,22+/m0/s1

> <INCHI_KEY>
CYSHNJQMYORNJI-YVNJGZBMSA-N

> <FORMULA>
C22H30O4

> <MOLECULAR_WEIGHT>
358.478

> <EXACT_MASS>
358.214409446

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
56

> <JCHEM_AVERAGE_POLARIZABILITY>
40.32244482134522

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(3R,3aS,4S,8aS)-3-hydroxy-6,8a-dimethyl-3-(propan-2-yl)-1,2,3,3a,4,5,8,8a-octahydroazulen-4-yl 4-hydroxybenzoate

> <ALOGPS_LOGP>
4.34

> <JCHEM_LOGP>
4.554228164666666

> <ALOGPS_LOGS>
-4.22

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.269329606210718

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.496322311953685

> <JCHEM_PKA_STRONGEST_BASIC>
-3.1183955506172376

> <JCHEM_POLAR_SURFACE_AREA>
66.76

> <JCHEM_REFRACTIVITY>
102.57659999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.15e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(3R,3aS,4S,8aS)-3-hydroxy-3-isopropyl-6,8a-dimethyl-1,2,3a,4,5,8-hexahydroazulen-4-yl 4-hydroxybenzoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 02-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   02-SEP-22         0                                  
HETATM    1  C   UNK     0       8.164   3.362   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       6.624   3.362   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       5.956   1.975   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       4.454   1.632   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       3.250   2.592   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.975   1.077   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.786   2.116   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.881   3.362   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.786   4.608   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       2.412   6.015   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       0.452   5.378   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -0.882   4.608   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       0.452   6.918   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       3.250   4.132   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.454   5.092   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       4.112   6.594   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       2.640   7.048   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       1.511   6.000   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       2.297   8.549   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       0.826   9.003   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       0.483  10.504   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       1.612  11.552   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       1.269  13.053   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0       3.084  11.098   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       3.426   9.596   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       5.956   4.750   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   26                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6    7   14                                             
CONECT    6    5                                                            
CONECT    7    5    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   11   14                                             
CONECT   10    9                                                            
CONECT   11    9   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11                                                            
CONECT   14    9    5   15                                                  
CONECT   15   14   16   26                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17   20   25                                                  
CONECT   20   19   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22   25                                                       
CONECT   25   24   19                                                       
CONECT   26   15    2                                                       
MASTER        0    0    0    0    0    0    0    0   26    0   56    0
END

View in JSmol

Synonyms

Value	Source
4-Oxy-6-(4-oxybezoyloxy)dauc-8,9-en	MeSH
Ferutinine	MeSH

Chemical Formula

C₂₂H₃₀O₄

Average Mass

358.4780 Da

Monoisotopic Mass

358.21441 Da

IUPAC Name

(3R,3aS,4S,8aS)-3-hydroxy-6,8a-dimethyl-3-(propan-2-yl)-1,2,3,3a,4,5,8,8a-octahydroazulen-4-yl 4-hydroxybenzoate

Traditional Name

(3R,3aS,4S,8aS)-3-hydroxy-3-isopropyl-6,8a-dimethyl-1,2,3a,4,5,8-hexahydroazulen-4-yl 4-hydroxybenzoate

CAS Registry Number

Not Available

SMILES

CC(C)[C@]1(O)CC[C@@]2(C)CC=C(C)C[C@H](OC(=O)C3=CC=C(O)C=C3)[C@@H]12

InChI Identifier

InChI=1S/C22H30O4/c1-14(2)22(25)12-11-21(4)10-9-15(3)13-18(19(21)22)26-20(24)16-5-7-17(23)8-6-16/h5-9,14,18-19,23,25H,10-13H2,1-4H3/t18-,19+,21+,22+/m0/s1

InChI Key

CYSHNJQMYORNJI-YVNJGZBMSA-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, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, 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
Ferula elaeochytris	LOTUS Database	35616633
Ferula hermonis	LOTUS Database	35616633
Ferula jaeschkeana	LOTUS Database	35616633
Ferula kuhistanica	LOTUS Database	35616633
Ferula ovina	LOTUS Database	35616633
Ferula tenuisecta	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Sesquiterpenoids

Direct Parent

Sesquiterpenoids

Alternative Parents

Substituents

Daucane sesquiterpenoid
Sesquiterpenoid
P-hydroxybenzoic acid alkyl ester
P-hydroxybenzoic acid ester
Benzoate ester
Benzoic acid or derivatives
Benzoyl
1-hydroxy-2-unsubstituted benzenoid
Phenol
Benzenoid
Monocyclic benzene moiety
Tertiary alcohol
Cyclic alcohol
Carboxylic acid ester
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Alcohol
Aromatic homopolycyclic compound

Molecular Framework

Aromatic homopolycyclic 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	4.34	ALOGPS
logP	4.55	ChemAxon
logS	-4.2	ALOGPS
pKa (Strongest Acidic)	8.5	ChemAxon
pKa (Strongest Basic)	-3.1	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	66.76 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	102.58 m³·mol⁻¹	ChemAxon
Polarizability	40.32 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

C00021389

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

91747167

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Aydogan F, Baykan S, Debelec Butuner B: Cytotoxic Activity of Sesquiterpenoids Isolated from Endemic Ferula tenuissima Hub.-Mor & Pesmen. Turk J Pharm Sci. 2019 Dec;16(4):476-480. doi: 10.4274/tjps.galenos.2018.23356. Epub 2019 Nov 11. [PubMed:32454752 ]
Aydogan F, Baykan S, Soliman GA, Yusufoglu H, Bedir E: Evaluation of the potential aphrodisiac activity of sesquiterpenoids from roots of Ferula huber-morathii Pesmen in male rats. J Ethnopharmacol. 2020 Jul 15;257:112868. doi: 10.1016/j.jep.2020.112868. Epub 2020 Apr 13. [PubMed:32298751 ]
Arjmand Z, Hamburger M, Dastan D: Isolation and purification of terpenoid compounds from Ferula haussknechtii and evaluation of their antibacterial effects. Nat Prod Res. 2023 May;37(10):1617-1624. doi: 10.1080/14786419.2022.2103558. Epub 2022 Jul 27. [PubMed:35895028 ]
Maiuolo J, Musolino V, Guarnieri L, Macri R, Coppoletta AR, Cardamone A, Serra M, Gliozzi M, Bava I, Lupia C, Tucci L, Bombardelli E, Mollace V: Ferula communis L. (Apiaceae) Root Acetone-Water Extract: Phytochemical Analysis, Cytotoxicity and In Vitro Evaluation of Estrogenic Properties. Plants (Basel). 2022 Jul 22;11(15):1905. doi: 10.3390/plants11151905. [PubMed:35893609 ]
Maity J, Barthels D, Sarkar J, Prateeksha P, Deb M, Rolph D, Das H: Ferutinin induces osteoblast differentiation of DPSCs via induction of KLF2 and autophagy/mitophagy. Cell Death Dis. 2022 May 12;13(5):452. doi: 10.1038/s41419-022-04903-9. [PubMed:35552354 ]
Hammam AMM, Elmotayam AK, Elnattat WM, Ali GA, Madbouly AEM, El Khatteb RM, Abdelhameed MF, Ali AH, Qasim S, Ahmed SR: Assessment of Ferula hermonis Boiss fertility effects in immature female rats supported by quantification of ferutinin via HPLC and molecular docking. J Ethnopharmacol. 2022 May 10;289:115062. doi: 10.1016/j.jep.2022.115062. Epub 2022 Feb 1. [PubMed:35114339 ]
Zare Mirakabad H, Khorramizadeh MR: Introduction to the potential of Ferula ovina in dental implant research due to estrogenic bioactive compounds and adhesive properties. PLoS One. 2022 Jan 18;17(1):e0262045. doi: 10.1371/journal.pone.0262045. eCollection 2022. [PubMed:35041680 ]
Gilbert-Girard S, Reigada I, Savijoki K, Yli-Kauhaluoma J, Fallarero A: Screening of natural compounds identifies ferutinin as an antibacterial and anti-biofilm compound. Biofouling. 2021 Aug;37(7):791-807. doi: 10.1080/08927014.2021.1971655. Epub 2021 Aug 30. [PubMed:34455871 ]
Maiuolo J, Bava I, Carresi C, Gliozzi M, Musolino V, Scicchitano M, Macri R, Oppedisano F, Scarano F, Caterina Zito M, Bosco F, Ruga S, Nucera S, Ilari S, Palma E, Muscoli C, Mollace V: The Effect of Ferula communis Extract in Escherichia coli Lipopolysaccharide-Induced Neuroinflammation in Cultured Neurons and Oligodendrocytes. Int J Mol Sci. 2021 Jul 24;22(15):7910. doi: 10.3390/ijms22157910. [PubMed:34360675 ]
Mahmoudi Z, Saidi A, Iranshahi M, Dadgar N, Azizsoltani A, Behzad S, Mahmoudi L, Soleimani M, Parsa Khankandi H: In vitro evaluation of ferutinin on proliferation and osteogenesis differentiation in human unrestricted Somatic stem cells. Steroids. 2021 Aug;172:108862. doi: 10.1016/j.steroids.2021.108862. Epub 2021 May 16. [PubMed:34010709 ]
Naji Reyhani Garmroudi S, Karimi E, Oskoueian E, Homayouni-Tabrizi M, Iranshahi M: Ferutinin: A phytoestrogen from ferula and its anticancer, antioxidant, and toxicity properties. J Biochem Mol Toxicol. 2021 Apr;35(4):e22713. doi: 10.1002/jbt.22713. Epub 2021 Jan 27. [PubMed:33501774 ]
Macri R, Musolino V, Gliozzi M, Carresi C, Maiuolo J, Nucera S, Scicchitano M, Bosco F, Scarano F, Ruga S, Zito MC, Guarnieri L, Bombardelli E, Mollace V: Ferula L. Plant Extracts and Dose-Dependent Activity of Natural Sesquiterpene Ferutinin: From Antioxidant Potential to Cytotoxic Effects. Molecules. 2020 Dec 7;25(23):5768. doi: 10.3390/molecules25235768. [PubMed:33297504 ]
Alilou M, Dibwe DF, Schwaiger S, Khodami M, Troppmair J, Awale S, Stuppner H: Antiausterity Activity of Secondary Metabolites from the Roots of Ferula hezarlalehzarica against the PANC-1 Human Pancreatic Cancer Cell Line. J Nat Prod. 2020 Apr 24;83(4):1099-1106. doi: 10.1021/acs.jnatprod.9b01109. Epub 2020 Mar 12. [PubMed:32163286 ]
Safi R, El-Sabban M, Najjar F: Ferula hermonis: A Review of Current Use and Pharmacological Studies of its Sesquiterpene Ester Ferutinin. Curr Drug Targets. 2020;21(5):499-508. doi: 10.2174/1389450120666191029155053. [PubMed:31663476 ]
LOTUS database [Link]

Showing NP-Card for (3r,3as,4s,8as)-3-hydroxy-3-isopropyl-6,8a-dimethyl-1,2,3a,4,5,8-hexahydroazulen-4-yl 4-hydroxybenzoate (NP0149718)

MOL for NP0149718 ((3r,3as,4s,8as)-3-hydroxy-3-isopropyl-6,8a-dimethyl-1,2,3a,4,5,8-hexahydroazulen-4-yl 4-hydroxybenzoate)

3D MOL for NP0149718 ((3r,3as,4s,8as)-3-hydroxy-3-isopropyl-6,8a-dimethyl-1,2,3a,4,5,8-hexahydroazulen-4-yl 4-hydroxybenzoate)

3D SDF for NP0149718 ((3r,3as,4s,8as)-3-hydroxy-3-isopropyl-6,8a-dimethyl-1,2,3a,4,5,8-hexahydroazulen-4-yl 4-hydroxybenzoate)

3D-SDF for NP0149718 ((3r,3as,4s,8as)-3-hydroxy-3-isopropyl-6,8a-dimethyl-1,2,3a,4,5,8-hexahydroazulen-4-yl 4-hydroxybenzoate)

PDB for NP0149718 ((3r,3as,4s,8as)-3-hydroxy-3-isopropyl-6,8a-dimethyl-1,2,3a,4,5,8-hexahydroazulen-4-yl 4-hydroxybenzoate)

3D PDB for NP0149718 ((3r,3as,4s,8as)-3-hydroxy-3-isopropyl-6,8a-dimethyl-1,2,3a,4,5,8-hexahydroazulen-4-yl 4-hydroxybenzoate)

SMILES for NP0149718 ((3r,3as,4s,8as)-3-hydroxy-3-isopropyl-6,8a-dimethyl-1,2,3a,4,5,8-hexahydroazulen-4-yl 4-hydroxybenzoate)

INCHI for NP0149718 ((3r,3as,4s,8as)-3-hydroxy-3-isopropyl-6,8a-dimethyl-1,2,3a,4,5,8-hexahydroazulen-4-yl 4-hydroxybenzoate)

Structure for NP0149718 ((3r,3as,4s,8as)-3-hydroxy-3-isopropyl-6,8a-dimethyl-1,2,3a,4,5,8-hexahydroazulen-4-yl 4-hydroxybenzoate)

3D Structure for NP0149718 ((3r,3as,4s,8as)-3-hydroxy-3-isopropyl-6,8a-dimethyl-1,2,3a,4,5,8-hexahydroazulen-4-yl 4-hydroxybenzoate)