NP-MRD: Showing NP-Card for (3r,3as,4r,8r,8as)-3,8-dihydroxy-3-isopropyl-6,8a-dimethyl-1-oxo-3a,4,5,8-tetrahydro-2h-azulen-4-yl 4-hydroxy-3-methoxybenzoate (NP0303430)

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Record Information

Version

2.0

Created at

2022-09-10 17:46:14 UTC

Updated at

2022-09-10 17:46:15 UTC

NP-MRD ID

NP0303430

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(3r,3as,4r,8r,8as)-3,8-dihydroxy-3-isopropyl-6,8a-dimethyl-1-oxo-3a,4,5,8-tetrahydro-2h-azulen-4-yl 4-hydroxy-3-methoxybenzoate

Description

Kuhistanicaol I belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units. (3r,3as,4r,8r,8as)-3,8-dihydroxy-3-isopropyl-6,8a-dimethyl-1-oxo-3a,4,5,8-tetrahydro-2h-azulen-4-yl 4-hydroxy-3-methoxybenzoate is found in Ferula kuhistanica. Based on a literature review very few articles have been published on Kuhistanicaol I.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309102219462D          

 30 32  0  0  1  0            999 V2000
    4.4326    5.6221    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6162    4.8178    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0114    4.2566    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1950    3.4523    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5902    2.8912    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7738    2.0868    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5621    1.8437    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1690    1.5257    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3526    0.7214    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.1569    0.5378    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5149   -0.2055    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3399   -0.2055    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1569   -0.9488    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3526   -1.1324    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.1690   -1.9367    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7076   -0.6180    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.5603   -1.4297    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9230   -0.8729    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6680   -1.6576    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4380   -0.2055    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9230    0.4619    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.2585    1.2156    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2085    0.8744    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2085    1.6994    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4940    0.4619    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7076    0.2070    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.8019    3.1343    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6183    3.9387    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2231    4.4998    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0395    5.3041    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
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  6  8  1  0  0  0  0
  9  8  1  6  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 11 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  1  0  0  0
 14 16  1  0  0  0  0
 16 17  1  6  0  0  0
 16 18  1  0  0  0  0
 18 19  2  0  0  0  0
 18 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  6  0  0  0
 21 23  1  1  0  0  0
 23 24  1  0  0  0  0
 23 25  1  0  0  0  0
 26 21  1  6  0  0  0
  9 26  1  0  0  0  0
 16 26  1  0  0  0  0
  5 27  2  0  0  0  0
 27 28  1  0  0  0  0
 28 29  2  0  0  0  0
  3 29  1  0  0  0  0
 29 30  1  0  0  0  0
M  END

     RDKit          3D

 60 62  0  0  0  0  0  0  0  0999 V2000
    4.8469    1.6553   -1.1731 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4656    1.4354    0.0866 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7637    0.7087    1.0629 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5007    0.2068    0.8341 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7901   -0.5119    1.7805 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4684   -0.9776    1.3950 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7425   -1.6431    2.1908 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8739   -0.7663    0.1871 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3820   -1.1892   -0.2272 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.3830   -2.2089   -1.3367 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4745   -1.9523   -2.3221 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4374   -3.0490   -2.6193 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7282   -0.8364   -3.0082 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9207    0.4335   -2.9105 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.3660    1.3579   -3.8285 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0153    0.9273   -1.4764 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0866    1.8285   -1.0924 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2854    1.7479   -1.4157 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7916    2.4229   -2.2809 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8593    1.5941   -0.0472 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9076    0.6183    0.6508 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.9619    1.3979    1.2963 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6112   -0.2014    1.6848 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8021   -0.9422    1.1891 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0453    0.7615    2.7951 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3806   -0.1410   -0.5109 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.3642   -0.7320    2.9888 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6313   -0.2418    3.2510 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3300    0.4760    2.2932 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6079    0.9792    2.5359 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7552    0.6679   -1.6509 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8371    2.0774   -1.0750 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4949    2.3005   -1.7912 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0681    0.4034   -0.1520 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7874   -1.7395    0.6577 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5555   -2.2310   -1.9169 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5348   -3.2567   -0.9781 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4325   -2.6343   -2.8706 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4714   -3.7826   -1.7822 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9889   -3.6146   -3.4872 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5769   -0.8339   -3.6891 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1299    0.1726   -3.1800 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1397    1.0804   -4.3518 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7439    1.5131   -0.2936 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7429    1.9736   -2.0014 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2403    2.8772   -0.8404 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8660    1.1979   -0.1534 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8454    2.5915    0.4372 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5912    0.9883    2.0941 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8994   -0.8874    2.1352 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5902   -1.5572    0.3139 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6787   -0.2999    0.9729 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1293   -1.6379    1.9994 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9549    0.2527    3.7829 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1095    1.0803    2.6347 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3724    1.6450    2.8395 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2732   -0.6730   -0.9665 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8393   -1.2819    3.7349 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1343   -0.3886    4.1964 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0613    0.8384    3.4086 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5 27  2  0
 27 28  1  0
 28 29  2  0
 29 30  1  0
  5  6  1  0
  6  7  2  0
  6  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 11 13  2  0
 13 14  1  0
 14 15  1  0
 14 16  1  0
 16 17  1  1
 16 26  1  0
 26 21  1  0
 21 22  1  1
 21 20  1  0
 20 18  1  0
 18 19  2  0
 21 23  1  0
 23 24  1  0
 23 25  1  0
 29  3  1  0
 26  9  1  0
 18 16  1  0
  1 31  1  0
  1 32  1  0
  1 33  1  0
  4 34  1  0
 27 58  1  0
 28 59  1  0
 30 60  1  0
  9 35  1  1
 10 36  1  0
 10 37  1  0
 12 38  1  0
 12 39  1  0
 12 40  1  0
 13 41  1  0
 14 42  1  6
 15 43  1  0
 17 44  1  0
 17 45  1  0
 17 46  1  0
 26 57  1  6
 22 49  1  0
 20 47  1  0
 20 48  1  0
 23 50  1  0
 24 51  1  0
 24 52  1  0
 24 53  1  0
 25 54  1  0
 25 55  1  0
 25 56  1  0
M  END


  Mrv1652309102219462D          

 30 32  0  0  1  0            999 V2000
    4.4326    5.6221    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6162    4.8178    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0114    4.2566    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1950    3.4523    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5902    2.8912    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7738    2.0868    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5621    1.8437    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1690    1.5257    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3526    0.7214    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.1569    0.5378    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5149   -0.2055    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3399   -0.2055    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1569   -0.9488    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3526   -1.1324    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.1690   -1.9367    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7076   -0.6180    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.5603   -1.4297    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9230   -0.8729    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6680   -1.6576    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4380   -0.2055    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9230    0.4619    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.2585    1.2156    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2085    0.8744    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2085    1.6994    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4940    0.4619    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7076    0.2070    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.8019    3.1343    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6183    3.9387    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2231    4.4998    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0395    5.3041    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
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  6  8  1  0  0  0  0
  9  8  1  6  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 11 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  1  0  0  0
 14 16  1  0  0  0  0
 16 17  1  6  0  0  0
 16 18  1  0  0  0  0
 18 19  2  0  0  0  0
 18 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  6  0  0  0
 21 23  1  1  0  0  0
 23 24  1  0  0  0  0
 23 25  1  0  0  0  0
 26 21  1  6  0  0  0
  9 26  1  0  0  0  0
 16 26  1  0  0  0  0
  5 27  2  0  0  0  0
 27 28  1  0  0  0  0
 28 29  2  0  0  0  0
  3 29  1  0  0  0  0
 29 30  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0303430

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC(=CC=C1O)C(=O)O[C@@H]1CC(C)=C[C@@H](O)[C@]2(C)[C@@H]1[C@@](O)(CC2=O)C(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C23H30O7/c1-12(2)23(28)11-19(26)22(4)18(25)9-13(3)8-17(20(22)23)30-21(27)14-6-7-15(24)16(10-14)29-5/h6-7,9-10,12,17-18,20,24-25,28H,8,11H2,1-5H3/t17-,18-,20-,22+,23-/m1/s1

> <INCHI_KEY>
OBKNOQAROVHENZ-YPBQMLHOSA-N

> <FORMULA>
C23H30O7

> <MOLECULAR_WEIGHT>
418.486

> <EXACT_MASS>
418.199153306

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
60

> <JCHEM_AVERAGE_POLARIZABILITY>
44.374432368620674

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <JCHEM_LOGP>
2.8102773906666663

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.772222963238306

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.990309633796308

> <JCHEM_PKA_STRONGEST_BASIC>
-3.1731403691819198

> <JCHEM_POLAR_SURFACE_AREA>
113.29000000000002

> <JCHEM_REFRACTIVITY>
110.9405

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(3R,3aS,4R,8R,8aS)-3,8-dihydroxy-3-isopropyl-6,8a-dimethyl-1-oxo-3a,4,5,8-tetrahydro-2H-azulen-4-yl 4-hydroxy-3-methoxybenzoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 10-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   10-SEP-22         0                                  
HETATM    1  C   UNK     0       8.274  10.495   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       8.617   8.993   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       7.488   7.946   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       7.831   6.444   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       6.702   5.397   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       7.044   3.895   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       8.516   3.442   0.000  0.00  0.00           O+0
HETATM    8  O   UNK     0       5.916   2.848   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       6.258   1.347   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       7.760   1.004   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       8.428  -0.384   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       9.968  -0.384   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       7.760  -1.771   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       6.258  -2.114   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       5.916  -3.615   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       5.054  -1.154   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       4.779  -2.669   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       3.590  -1.629   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       3.114  -3.094   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       2.684  -0.384   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       3.590   0.862   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       4.216   2.269   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       2.256   1.632   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       2.256   3.172   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       0.922   0.862   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       5.054   0.386   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       5.230   5.851   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       4.887   7.352   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       6.016   8.400   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0       5.674   9.901   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   29                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6   27                                                  
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9                                                       
CONECT    9    8   10   26                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14                                                       
CONECT   14   13   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14   17   18   26                                             
CONECT   17   16                                                            
CONECT   18   16   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18   21                                                       
CONECT   21   20   22   23   26                                             
CONECT   22   21                                                            
CONECT   23   21   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23                                                            
CONECT   26   21    9   16                                                  
CONECT   27    5   28                                                       
CONECT   28   27   29                                                       
CONECT   29   28    3   30                                                  
CONECT   30   29                                                            
MASTER        0    0    0    0    0    0    0    0   30    0   64    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₃H₃₀O₇

Average Mass

418.4860 Da

Monoisotopic Mass

418.19915 Da

IUPAC Name

(3R,3aS,4R,8R,8aS)-3,8-dihydroxy-6,8a-dimethyl-1-oxo-3-(propan-2-yl)-1,2,3,3a,4,5,8,8a-octahydroazulen-4-yl 4-hydroxy-3-methoxybenzoate

Traditional Name

(3R,3aS,4R,8R,8aS)-3,8-dihydroxy-3-isopropyl-6,8a-dimethyl-1-oxo-3a,4,5,8-tetrahydro-2H-azulen-4-yl 4-hydroxy-3-methoxybenzoate

CAS Registry Number

Not Available

SMILES

COC1=CC(=CC=C1O)C(=O)O[C@@H]1CC(C)=C[C@@H](O)[C@]2(C)[C@@H]1[C@@](O)(CC2=O)C(C)C

InChI Identifier

InChI=1S/C23H30O7/c1-12(2)23(28)11-19(26)22(4)18(25)9-13(3)8-17(20(22)23)30-21(27)14-6-7-15(24)16(10-14)29-5/h6-7,9-10,12,17-18,20,24-25,28H,8,11H2,1-5H3/t17-,18-,20-,22+,23-/m1/s1

InChI Key

OBKNOQAROVHENZ-YPBQMLHOSA-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 kuhistanica	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

Sesquiterpenoid
Daucane sesquiterpenoid
M-methoxybenzoic acid or derivatives
P-hydroxybenzoic acid alkyl ester
P-hydroxybenzoic acid ester
Methoxyphenol
Benzoate ester
Benzoic acid or derivatives
Methoxybenzene
Phenol ether
Phenoxy compound
Benzoyl
Anisole
Alkyl aryl ether
1-hydroxy-2-unsubstituted benzenoid
Phenol
Benzenoid
Monocyclic benzene moiety
Tertiary alcohol
Cyclic alcohol
Secondary alcohol
Carboxylic acid ester
Ketone
Monocarboxylic acid or derivatives
Ether
Carboxylic acid derivative
Alcohol
Organooxygen compound
Hydrocarbon derivative
Organic oxygen compound
Carbonyl group
Organic oxide
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	2.81	ChemAxon
pKa (Strongest Acidic)	8.99	ChemAxon
pKa (Strongest Basic)	-3.2	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	113.29 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	110.94 m³·mol⁻¹	ChemAxon
Polarizability	44.37 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

C00037404

Chemspider ID

552270

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

636500

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (3r,3as,4r,8r,8as)-3,8-dihydroxy-3-isopropyl-6,8a-dimethyl-1-oxo-3a,4,5,8-tetrahydro-2h-azulen-4-yl 4-hydroxy-3-methoxybenzoate (NP0303430)

MOL for NP0303430 ((3r,3as,4r,8r,8as)-3,8-dihydroxy-3-isopropyl-6,8a-dimethyl-1-oxo-3a,4,5,8-tetrahydro-2h-azulen-4-yl 4-hydroxy-3-methoxybenzoate)

3D MOL for NP0303430 ((3r,3as,4r,8r,8as)-3,8-dihydroxy-3-isopropyl-6,8a-dimethyl-1-oxo-3a,4,5,8-tetrahydro-2h-azulen-4-yl 4-hydroxy-3-methoxybenzoate)

3D SDF for NP0303430 ((3r,3as,4r,8r,8as)-3,8-dihydroxy-3-isopropyl-6,8a-dimethyl-1-oxo-3a,4,5,8-tetrahydro-2h-azulen-4-yl 4-hydroxy-3-methoxybenzoate)

3D-SDF for NP0303430 ((3r,3as,4r,8r,8as)-3,8-dihydroxy-3-isopropyl-6,8a-dimethyl-1-oxo-3a,4,5,8-tetrahydro-2h-azulen-4-yl 4-hydroxy-3-methoxybenzoate)

PDB for NP0303430 ((3r,3as,4r,8r,8as)-3,8-dihydroxy-3-isopropyl-6,8a-dimethyl-1-oxo-3a,4,5,8-tetrahydro-2h-azulen-4-yl 4-hydroxy-3-methoxybenzoate)

3D PDB for NP0303430 ((3r,3as,4r,8r,8as)-3,8-dihydroxy-3-isopropyl-6,8a-dimethyl-1-oxo-3a,4,5,8-tetrahydro-2h-azulen-4-yl 4-hydroxy-3-methoxybenzoate)

SMILES for NP0303430 ((3r,3as,4r,8r,8as)-3,8-dihydroxy-3-isopropyl-6,8a-dimethyl-1-oxo-3a,4,5,8-tetrahydro-2h-azulen-4-yl 4-hydroxy-3-methoxybenzoate)

INCHI for NP0303430 ((3r,3as,4r,8r,8as)-3,8-dihydroxy-3-isopropyl-6,8a-dimethyl-1-oxo-3a,4,5,8-tetrahydro-2h-azulen-4-yl 4-hydroxy-3-methoxybenzoate)

Structure for NP0303430 ((3r,3as,4r,8r,8as)-3,8-dihydroxy-3-isopropyl-6,8a-dimethyl-1-oxo-3a,4,5,8-tetrahydro-2h-azulen-4-yl 4-hydroxy-3-methoxybenzoate)

3D Structure for NP0303430 ((3r,3as,4r,8r,8as)-3,8-dihydroxy-3-isopropyl-6,8a-dimethyl-1-oxo-3a,4,5,8-tetrahydro-2h-azulen-4-yl 4-hydroxy-3-methoxybenzoate)