NP-MRD: Showing NP-Card for nardoguaianone B (NP0029883)

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Record Information

Version

2.0

Created at

2021-06-19 21:23:31 UTC

Updated at

2021-06-29 23:57:32 UTC

NP-MRD ID

NP0029883

Secondary Accession Numbers

None

Natural Product Identification

Common Name

nardoguaianone B

Provided By

JEOL Database JEOL Logo

Description

Nardoperoxide belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units. nardoguaianone B is found in Nardostachys chinensis. nardoguaianone B was first documented in 2000 (Takaya, Y., et al.). Based on a literature review very few articles have been published on nardoperoxide.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306192123233D          

 41 43  0  0  0  0            999 V2000
    3.5647   -0.0753    1.8745 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7325    0.3547    0.6606 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.4032   -0.1601   -0.6197 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2093   -0.0046    0.7700 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.5893    0.7118    1.9947 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.8658    1.1158    1.7067 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.5281    0.1674    0.6924 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.9155    0.6798    0.3054 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7777    0.1006   -0.5520 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5788    0.6304   -0.3728 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4947   -1.2293    1.2193 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4146   -2.0257    1.2313 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6537   -3.4047    1.7885 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.3762   -4.5228    0.7882 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1284   -3.3850    2.2097 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.5789   -2.0043    1.8286 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7014   -1.5676    2.0292 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9553   -1.5673    0.7961 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.1817   -2.1383   -0.4895 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6419   -1.1637    1.9533 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1463    0.3075    2.8097 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5847    0.3172    1.7927 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7956    1.4512    0.5982 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3978    0.2866   -0.7313 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8265    0.1031   -1.5116 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5394   -1.2456   -0.5997 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1362    1.6325    2.2345 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6531    0.0804    2.8892 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8560    2.1324    1.2902 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4305    1.1644    2.6457 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8367    1.6326   -0.2317 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4189   -0.0147   -0.3775 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5557    0.8398    1.1787 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0264   -3.5586    2.6752 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9326   -4.3781   -0.1447 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6894   -4.5748    0.5419 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6638   -5.4935    1.2064 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7357   -4.1290    1.6858 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2288   -3.5133    3.2920 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6688   -2.0221    1.4906 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7035   -1.5594   -1.1169 H   0  0  0  0  0  0  0  0  0  0  0  0
 11 16  1  0  0  0  0
  6  5  1  0  0  0  0
  4  5  1  0  0  0  0
 12 11  2  0  0  0  0
 16 17  2  0  0  0  0
 16 15  1  0  0  0  0
  7  8  1  6  0  0  0
 11  7  1  0  0  0  0
  4  2  1  6  0  0  0
 15 13  1  0  0  0  0
 18 19  1  0  0  0  0
 12 18  1  0  0  0  0
 13 14  1  0  0  0  0
 13 12  1  0  0  0  0
  7  9  1  0  0  0  0
  7  6  1  0  0  0  0
  4 10  1  0  0  0  0
  2  1  1  0  0  0  0
 18  4  1  0  0  0  0
  2  3  1  0  0  0  0
 10  9  1  0  0  0  0
 15 38  1  0  0  0  0
 15 39  1  0  0  0  0
 13 34  1  1  0  0  0
 18 40  1  1  0  0  0
  6 29  1  0  0  0  0
  6 30  1  0  0  0  0
  5 27  1  0  0  0  0
  5 28  1  0  0  0  0
  8 31  1  0  0  0  0
  8 32  1  0  0  0  0
  8 33  1  0  0  0  0
  2 23  1  6  0  0  0
 19 41  1  0  0  0  0
 14 35  1  0  0  0  0
 14 36  1  0  0  0  0
 14 37  1  0  0  0  0
  1 20  1  0  0  0  0
  1 21  1  0  0  0  0
  1 22  1  0  0  0  0
  3 24  1  0  0  0  0
  3 25  1  0  0  0  0
  3 26  1  0  0  0  0
M  END

     RDKit          3D

 41 43  0  0  0  0  0  0  0  0999 V2000
    3.5647   -0.0753    1.8745 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7325    0.3547    0.6606 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.4032   -0.1601   -0.6197 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2093   -0.0046    0.7700 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.5893    0.7118    1.9947 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8658    1.1158    1.7067 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5281    0.1674    0.6924 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.9155    0.6798    0.3054 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7777    0.1006   -0.5520 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5788    0.6304   -0.3728 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4947   -1.2293    1.2193 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4146   -2.0257    1.2313 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6537   -3.4047    1.7885 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.3762   -4.5228    0.7882 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1284   -3.3850    2.2097 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5789   -2.0043    1.8286 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7014   -1.5676    2.0292 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9553   -1.5673    0.7961 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.1817   -2.1383   -0.4895 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6419   -1.1637    1.9533 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1463    0.3075    2.8097 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5847    0.3172    1.7927 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7956    1.4512    0.5982 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3978    0.2866   -0.7313 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8265    0.1031   -1.5116 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5394   -1.2456   -0.5997 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1362    1.6325    2.2345 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6531    0.0804    2.8892 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8560    2.1324    1.2902 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4305    1.1644    2.6457 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8367    1.6326   -0.2317 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4189   -0.0147   -0.3775 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5557    0.8398    1.1787 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0264   -3.5586    2.6752 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9326   -4.3781   -0.1447 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6894   -4.5748    0.5419 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6638   -5.4935    1.2064 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7357   -4.1290    1.6858 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2288   -3.5133    3.2920 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6688   -2.0221    1.4906 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7035   -1.5594   -1.1169 H   0  0  0  0  0  0  0  0  0  0  0  0
 11 16  1  0
  6  5  1  0
  4  5  1  0
 12 11  2  0
 16 17  2  0
 16 15  1  0
  7  8  1  6
 11  7  1  0
  4  2  1  6
 15 13  1  0
 18 19  1  0
 12 18  1  0
 13 14  1  0
 13 12  1  0
  7  9  1  0
  7  6  1  0
  4 10  1  0
  2  1  1  0
 18  4  1  0
  2  3  1  0
 10  9  1  0
 15 38  1  0
 15 39  1  0
 13 34  1  1
 18 40  1  1
  6 29  1  0
  6 30  1  0
  5 27  1  0
  5 28  1  0
  8 31  1  0
  8 32  1  0
  8 33  1  0
  2 23  1  6
 19 41  1  0
 14 35  1  0
 14 36  1  0
 14 37  1  0
  1 20  1  0
  1 21  1  0
  1 22  1  0
  3 24  1  0
  3 25  1  0
  3 26  1  0
M  END


  Mrv1652306192123233D          

 41 43  0  0  0  0            999 V2000
    3.5647   -0.0753    1.8745 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7325    0.3547    0.6606 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.4032   -0.1601   -0.6197 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2093   -0.0046    0.7700 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.5893    0.7118    1.9947 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.8658    1.1158    1.7067 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.5281    0.1674    0.6924 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.9155    0.6798    0.3054 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7777    0.1006   -0.5520 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5788    0.6304   -0.3728 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4947   -1.2293    1.2193 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4146   -2.0257    1.2313 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6537   -3.4047    1.7885 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.3762   -4.5228    0.7882 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1284   -3.3850    2.2097 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.5789   -2.0043    1.8286 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7014   -1.5676    2.0292 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9553   -1.5673    0.7961 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.1817   -2.1383   -0.4895 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6419   -1.1637    1.9533 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1463    0.3075    2.8097 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5847    0.3172    1.7927 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7956    1.4512    0.5982 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3978    0.2866   -0.7313 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8265    0.1031   -1.5116 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5394   -1.2456   -0.5997 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1362    1.6325    2.2345 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6531    0.0804    2.8892 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8560    2.1324    1.2902 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4305    1.1644    2.6457 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8367    1.6326   -0.2317 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4189   -0.0147   -0.3775 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5557    0.8398    1.1787 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0264   -3.5586    2.6752 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9326   -4.3781   -0.1447 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6894   -4.5748    0.5419 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6638   -5.4935    1.2064 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7357   -4.1290    1.6858 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2288   -3.5133    3.2920 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6688   -2.0221    1.4906 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7035   -1.5594   -1.1169 H   0  0  0  0  0  0  0  0  0  0  0  0
 11 16  1  0  0  0  0
  6  5  1  0  0  0  0
  4  5  1  0  0  0  0
 12 11  2  0  0  0  0
 16 17  2  0  0  0  0
 16 15  1  0  0  0  0
  7  8  1  6  0  0  0
 11  7  1  0  0  0  0
  4  2  1  6  0  0  0
 15 13  1  0  0  0  0
 18 19  1  0  0  0  0
 12 18  1  0  0  0  0
 13 14  1  0  0  0  0
 13 12  1  0  0  0  0
  7  9  1  0  0  0  0
  7  6  1  0  0  0  0
  4 10  1  0  0  0  0
  2  1  1  0  0  0  0
 18  4  1  0  0  0  0
  2  3  1  0  0  0  0
 10  9  1  0  0  0  0
 15 38  1  0  0  0  0
 15 39  1  0  0  0  0
 13 34  1  1  0  0  0
 18 40  1  1  0  0  0
  6 29  1  0  0  0  0
  6 30  1  0  0  0  0
  5 27  1  0  0  0  0
  5 28  1  0  0  0  0
  8 31  1  0  0  0  0
  8 32  1  0  0  0  0
  8 33  1  0  0  0  0
  2 23  1  6  0  0  0
 19 41  1  0  0  0  0
 14 35  1  0  0  0  0
 14 36  1  0  0  0  0
 14 37  1  0  0  0  0
  1 20  1  0  0  0  0
  1 21  1  0  0  0  0
  1 22  1  0  0  0  0
  3 24  1  0  0  0  0
  3 25  1  0  0  0  0
  3 26  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0029883

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]O[C@]1([H])C2=C(C(=O)C([H])([H])[C@@]2([H])C([H])([H])[H])[C@@]2(OO[C@]1(C([H])([H])C2([H])[H])C([H])(C([H])([H])[H])C([H])([H])[H])C([H])([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C15H22O4/c1-8(2)15-6-5-14(4,18-19-15)12-10(16)7-9(3)11(12)13(15)17/h8-9,13,17H,5-7H2,1-4H3/t9-,13-,14-,15-/m1/s1

> <INCHI_KEY>
BDBRZURCDWHOCK-SEWBAHNZSA-N

> <FORMULA>
C15H22O4

> <MOLECULAR_WEIGHT>
266.337

> <EXACT_MASS>
266.151809188

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
41

> <JCHEM_AVERAGE_POLARIZABILITY>
28.553402732278432

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1R,5R,7R,8R)-7-hydroxy-1,5-dimethyl-8-(propan-2-yl)-9,10-dioxatricyclo[6.2.2.0^{2,6}]dodec-2(6)-en-3-one

> <ALOGPS_LOGP>
1.77

> <JCHEM_LOGP>
2.0953560246666667

> <ALOGPS_LOGS>
-1.99

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
19.853448562624905

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.251113554157815

> <JCHEM_PKA_STRONGEST_BASIC>
-3.563762800038673

> <JCHEM_POLAR_SURFACE_AREA>
55.760000000000005

> <JCHEM_REFRACTIVITY>
70.1639

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.75e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1R,5R,7R,8R)-7-hydroxy-8-isopropyl-1,5-dimethyl-9,10-dioxatricyclo[6.2.2.0^{2,6}]dodec-2(6)-en-3-one

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 41 43  0  0  0  0  0  0  0  0999 V2000
    3.5647   -0.0753    1.8745 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7325    0.3547    0.6606 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.4032   -0.1601   -0.6197 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2093   -0.0046    0.7700 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.5893    0.7118    1.9947 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8658    1.1158    1.7067 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5281    0.1674    0.6924 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.9155    0.6798    0.3054 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7777    0.1006   -0.5520 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5788    0.6304   -0.3728 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4947   -1.2293    1.2193 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4146   -2.0257    1.2313 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6537   -3.4047    1.7885 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.3762   -4.5228    0.7882 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1284   -3.3850    2.2097 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5789   -2.0043    1.8286 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7014   -1.5676    2.0292 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9553   -1.5673    0.7961 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.1817   -2.1383   -0.4895 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6419   -1.1637    1.9533 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1463    0.3075    2.8097 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5847    0.3172    1.7927 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7956    1.4512    0.5982 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3978    0.2866   -0.7313 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8265    0.1031   -1.5116 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5394   -1.2456   -0.5997 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1362    1.6325    2.2345 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6531    0.0804    2.8892 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8560    2.1324    1.2902 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4305    1.1644    2.6457 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8367    1.6326   -0.2317 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4189   -0.0147   -0.3775 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5557    0.8398    1.1787 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0264   -3.5586    2.6752 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9326   -4.3781   -0.1447 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6894   -4.5748    0.5419 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6638   -5.4935    1.2064 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7357   -4.1290    1.6858 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2288   -3.5133    3.2920 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6688   -2.0221    1.4906 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7035   -1.5594   -1.1169 H   0  0  0  0  0  0  0  0  0  0  0  0
 11 16  1  0
  6  5  1  0
  4  5  1  0
 12 11  2  0
 16 17  2  0
 16 15  1  0
  7  8  1  6
 11  7  1  0
  4  2  1  6
 15 13  1  0
 18 19  1  0
 12 18  1  0
 13 14  1  0
 13 12  1  0
  7  9  1  0
  7  6  1  0
  4 10  1  0
  2  1  1  0
 18  4  1  0
  2  3  1  0
 10  9  1  0
 15 38  1  0
 15 39  1  0
 13 34  1  1
 18 40  1  1
  6 29  1  0
  6 30  1  0
  5 27  1  0
  5 28  1  0
  8 31  1  0
  8 32  1  0
  8 33  1  0
  2 23  1  6
 19 41  1  0
 14 35  1  0
 14 36  1  0
 14 37  1  0
  1 20  1  0
  1 21  1  0
  1 22  1  0
  3 24  1  0
  3 25  1  0
  3 26  1  0
M  END

HEADER    PROTEIN                                 19-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   19-JUN-21         0                                  
HETATM    1  C   UNK     0       3.565  -0.075   1.875  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.732   0.355   0.661  0.00  0.00           C+0
HETATM    3  C   UNK     0       3.403  -0.160  -0.620  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.209  -0.005   0.770  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.589   0.712   1.995  0.00  0.00           C+0
HETATM    6  C   UNK     0      -0.866   1.116   1.707  0.00  0.00           C+0
HETATM    7  C   UNK     0      -1.528   0.167   0.692  0.00  0.00           C+0
HETATM    8  C   UNK     0      -2.916   0.680   0.305  0.00  0.00           C+0
HETATM    9  O   UNK     0      -0.778   0.101  -0.552  0.00  0.00           O+0
HETATM   10  O   UNK     0       0.579   0.630  -0.373  0.00  0.00           O+0
HETATM   11  C   UNK     0      -1.495  -1.229   1.219  0.00  0.00           C+0
HETATM   12  C   UNK     0      -0.415  -2.026   1.231  0.00  0.00           C+0
HETATM   13  C   UNK     0      -0.654  -3.405   1.789  0.00  0.00           C+0
HETATM   14  C   UNK     0      -0.376  -4.523   0.788  0.00  0.00           C+0
HETATM   15  C   UNK     0      -2.128  -3.385   2.210  0.00  0.00           C+0
HETATM   16  C   UNK     0      -2.579  -2.004   1.829  0.00  0.00           C+0
HETATM   17  O   UNK     0      -3.701  -1.568   2.029  0.00  0.00           O+0
HETATM   18  C   UNK     0       0.955  -1.567   0.796  0.00  0.00           C+0
HETATM   19  O   UNK     0       1.182  -2.138  -0.490  0.00  0.00           O+0
HETATM   20  H   UNK     0       3.642  -1.164   1.953  0.00  0.00           H+0
HETATM   21  H   UNK     0       3.146   0.308   2.810  0.00  0.00           H+0
HETATM   22  H   UNK     0       4.585   0.317   1.793  0.00  0.00           H+0
HETATM   23  H   UNK     0       2.796   1.451   0.598  0.00  0.00           H+0
HETATM   24  H   UNK     0       4.398   0.287  -0.731  0.00  0.00           H+0
HETATM   25  H   UNK     0       2.826   0.103  -1.512  0.00  0.00           H+0
HETATM   26  H   UNK     0       3.539  -1.246  -0.600  0.00  0.00           H+0
HETATM   27  H   UNK     0       1.136   1.633   2.235  0.00  0.00           H+0
HETATM   28  H   UNK     0       0.653   0.080   2.889  0.00  0.00           H+0
HETATM   29  H   UNK     0      -0.856   2.132   1.290  0.00  0.00           H+0
HETATM   30  H   UNK     0      -1.431   1.164   2.646  0.00  0.00           H+0
HETATM   31  H   UNK     0      -2.837   1.633  -0.232  0.00  0.00           H+0
HETATM   32  H   UNK     0      -3.419  -0.015  -0.378  0.00  0.00           H+0
HETATM   33  H   UNK     0      -3.556   0.840   1.179  0.00  0.00           H+0
HETATM   34  H   UNK     0      -0.026  -3.559   2.675  0.00  0.00           H+0
HETATM   35  H   UNK     0      -0.933  -4.378  -0.145  0.00  0.00           H+0
HETATM   36  H   UNK     0       0.689  -4.575   0.542  0.00  0.00           H+0
HETATM   37  H   UNK     0      -0.664  -5.494   1.206  0.00  0.00           H+0
HETATM   38  H   UNK     0      -2.736  -4.129   1.686  0.00  0.00           H+0
HETATM   39  H   UNK     0      -2.229  -3.513   3.292  0.00  0.00           H+0
HETATM   40  H   UNK     0       1.669  -2.022   1.491  0.00  0.00           H+0
HETATM   41  H   UNK     0       0.704  -1.559  -1.117  0.00  0.00           H+0
CONECT    1    2   20   21   22                                             
CONECT    2    4    1    3   23                                             
CONECT    3    2   24   25   26                                             
CONECT    4    5    2   10   18                                             
CONECT    5    6    4   27   28                                             
CONECT    6    5    7   29   30                                             
CONECT    7    8   11    9    6                                             
CONECT    8    7   31   32   33                                             
CONECT    9    7   10                                                       
CONECT   10    4    9                                                       
CONECT   11   16   12    7                                                  
CONECT   12   11   18   13                                                  
CONECT   13   15   14   12   34                                             
CONECT   14   13   35   36   37                                             
CONECT   15   16   13   38   39                                             
CONECT   16   11   17   15                                                  
CONECT   17   16                                                            
CONECT   18   19   12    4   40                                             
CONECT   19   18   41                                                       
CONECT   20    1                                                            
CONECT   21    1                                                            
CONECT   22    1                                                            
CONECT   23    2                                                            
CONECT   24    3                                                            
CONECT   25    3                                                            
CONECT   26    3                                                            
CONECT   27    5                                                            
CONECT   28    5                                                            
CONECT   29    6                                                            
CONECT   30    6                                                            
CONECT   31    8                                                            
CONECT   32    8                                                            
CONECT   33    8                                                            
CONECT   34   13                                                            
CONECT   35   14                                                            
CONECT   36   14                                                            
CONECT   37   14                                                            
CONECT   38   15                                                            
CONECT   39   15                                                            
CONECT   40   18                                                            
CONECT   41   19                                                            
MASTER        0    0    0    0    0    0    0    0   41    0   86    0
END

RDKit          3D

41 43  0  0  0  0  0  0  0  0999 V2000
    3.5647   -0.0753    1.8745 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7325    0.3547    0.6606 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.4032   -0.1601   -0.6197 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2093   -0.0046    0.7700 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.5893    0.7118    1.9947 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8658    1.1158    1.7067 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5281    0.1674    0.6924 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.9155    0.6798    0.3054 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7777    0.1006   -0.5520 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5788    0.6304   -0.3728 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4947   -1.2293    1.2193 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4146   -2.0257    1.2313 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6537   -3.4047    1.7885 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.3762   -4.5228    0.7882 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1284   -3.3850    2.2097 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5789   -2.0043    1.8286 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7014   -1.5676    2.0292 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9553   -1.5673    0.7961 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.1817   -2.1383   -0.4895 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6419   -1.1637    1.9533 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1463    0.3075    2.8097 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5847    0.3172    1.7927 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7956    1.4512    0.5982 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3978    0.2866   -0.7313 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8265    0.1031   -1.5116 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5394   -1.2456   -0.5997 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1362    1.6325    2.2345 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6531    0.0804    2.8892 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8560    2.1324    1.2902 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4305    1.1644    2.6457 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8367    1.6326   -0.2317 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4189   -0.0147   -0.3775 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5557    0.8398    1.1787 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0264   -3.5586    2.6752 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9326   -4.3781   -0.1447 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6894   -4.5748    0.5419 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6638   -5.4935    1.2064 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7357   -4.1290    1.6858 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2288   -3.5133    3.2920 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6688   -2.0221    1.4906 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7035   -1.5594   -1.1169 H   0  0  0  0  0  0  0  0  0  0  0  0
 11 16  1  0
  6  5  1  0
  4  5  1  0
 12 11  2  0
 16 17  2  0
 16 15  1  0
  7  8  1  6
 11  7  1  0
  4  2  1  6
 15 13  1  0
 18 19  1  0
 12 18  1  0
 13 14  1  0
 13 12  1  0
  7  9  1  0
  7  6  1  0
  4 10  1  0
  2  1  1  0
 18  4  1  0
  2  3  1  0
 10  9  1  0
 15 38  1  0
 15 39  1  0
 13 34  1  1
 18 40  1  1
  6 29  1  0
  6 30  1  0
  5 27  1  0
  5 28  1  0
  8 31  1  0
  8 32  1  0
  8 33  1  0
  2 23  1  6
 19 41  1  0
 14 35  1  0
 14 36  1  0
 14 37  1  0
  1 20  1  0
  1 21  1  0
  1 22  1  0
  3 24  1  0
  3 25  1  0
  3 26  1  0
M  END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₅H₂₂O₄

Average Mass

266.3370 Da

Monoisotopic Mass

266.15181 Da

IUPAC Name

(1R,5R,7R,8R)-7-hydroxy-1,5-dimethyl-8-(propan-2-yl)-9,10-dioxatricyclo[6.2.2.0^{2,6}]dodec-2(6)-en-3-one

Traditional Name

(1R,5R,7R,8R)-7-hydroxy-8-isopropyl-1,5-dimethyl-9,10-dioxatricyclo[6.2.2.0^{2,6}]dodec-2(6)-en-3-one

CAS Registry Number

Not Available

SMILES

[H]O[C@]1([H])C2=C(C(=O)C([H])([H])[C@@]2([H])C([H])([H])[H])[C@@]2(OO[C@]1(C([H])([H])C2([H])[H])C([H])(C([H])([H])[H])C([H])([H])[H])C([H])([H])[H]

InChI Identifier

InChI=1S/C15H22O4/c1-8(2)15-6-5-14(4,18-19-15)12-10(16)7-9(3)11(12)13(15)17/h8-9,13,17H,5-7H2,1-4H3/t9-,13-,14-,15-/m1/s1

InChI Key

BDBRZURCDWHOCK-SEWBAHNZSA-N

Experimental Spectra

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

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Nardostachys jatamansi	JEOL database	Takaya, Y., et al, Tetrahedron 56, 7673 (2000)

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
Ortho-dioxane
Dialkyl peroxide
Secondary alcohol
Ketone
Oxacycle
Organoheterocyclic compound
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Alcohol
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

secondary alcohol (CHEBI:66611 )
enone (CHEBI:66611 )
sesquiterpenoid (CHEBI:66611 )
organic peroxide (CHEBI:66611 )
azulenes (CHEBI:66611 )

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	1.77	ALOGPS
logP	2.1	ChemAxon
logS	-2	ALOGPS
pKa (Strongest Acidic)	13.25	ChemAxon
pKa (Strongest Basic)	-3.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	55.76 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	70.16 m³·mol⁻¹	ChemAxon
Polarizability	28.55 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

Not Available

Chemspider ID

8643538

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

66611

Good Scents ID

Not Available

References

General References

Takaya, Y., et al. (2000). Takaya, Y., et al, Tetrahedron 56, 7673 (2000). Tetrahedron.

Showing NP-Card for nardoguaianone B (NP0029883)

MOL for NP0029883 (nardoguaianone B)

3D MOL for NP0029883 (nardoguaianone B)

3D SDF for NP0029883 (nardoguaianone B)

3D-SDF for NP0029883 (nardoguaianone B)

PDB for NP0029883 (nardoguaianone B)

3D PDB for NP0029883 (nardoguaianone B)

SMILES for NP0029883 (nardoguaianone B)

INCHI for NP0029883 (nardoguaianone B)

Structure for NP0029883 (nardoguaianone B)

3D Structure for NP0029883 (nardoguaianone B)