NP-MRD: Showing NP-Card for 2,3-Epoxyjaeschkeanadiol 5alpha-vanillate (NP0064440)

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Record Information

Version

2.0

Created at

2022-04-28 08:40:38 UTC

Updated at

2022-04-28 08:40:38 UTC

NP-MRD ID

NP0064440

Secondary Accession Numbers

None

Natural Product Identification

Common Name

2,3-Epoxyjaeschkeanadiol 5alpha-vanillate

Description

(1AS,2aR,5R,5aS,6S,7aR)-5-hydroxy-2a,7a-dimethyl-5-(propan-2-yl)-decahydroazuleno[5,6-b]oxiren-6-yl 4-hydroxy-3-methoxybenzoate belongs to the class of organic compounds known as m-methoxybenzoic acids and derivatives. These are benzoic acids in which the hydrogen atom at position 3 of the benzene ring is replaced by a methoxy group. 2,3-Epoxyjaeschkeanadiol 5alpha-vanillate is found in Ferula hermonis and Ferula orientalis. Based on a literature review very few articles have been published on (1aS,2aR,5R,5aS,6S,7aR)-5-hydroxy-2a,7a-dimethyl-5-(propan-2-yl)-decahydroazuleno[5,6-b]oxiren-6-yl 4-hydroxy-3-methoxybenzoate.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304282210402D          

 29 32  0  0  1  0            999 V2000
    3.6631    1.1824    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.8226    0.3730    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.2892   -0.2564    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.4645   -0.2317    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9696    0.4283    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.1771    1.2268    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.9308    1.5624    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3819    1.0073    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3484   -0.1145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6248   -1.0100    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1399   -1.6775    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3194   -1.5913    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4755   -2.4311    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2960   -2.5173    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6316   -3.2710    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1467   -3.9384    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3262   -3.8523    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9906   -3.0986    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4823   -4.6921    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4521   -3.3572    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7877   -4.1108    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6417    0.2746    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.9884    1.0232    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3836    1.5843    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3454   -0.1559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0701    0.2383    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3245   -0.9807    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6380   -0.5504    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6507    2.0073    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  6  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  1  7  1  0  0  0  0
  6  8  1  1  0  0  0
  5  8  1  0  0  0  0
  5  9  1  6  0  0  0
  3 10  1  1  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 11 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 13 18  1  0  0  0  0
 16 19  1  0  0  0  0
 15 20  1  0  0  0  0
 20 21  1  0  0  0  0
  2 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
  1 24  1  0  0  0  0
 22 25  1  1  0  0  0
 25 26  1  0  0  0  0
 25 27  1  0  0  0  0
 22 28  1  6  0  0  0
  1 29  1  6  0  0  0
M  END

     RDKit          3D

 61 64  0  0  0  0  0  0  0  0999 V2000
    4.5997   -1.6680   -2.0838 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0702   -2.3985   -0.9503 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3640   -2.2897    0.2517 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2378   -1.5032    0.3646 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5204   -1.3735    1.5294 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3323   -0.5361    1.6267 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6735   -0.4135    2.6890 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8456    0.1896    0.5374 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2919    1.0075    0.5830 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.1725    2.4488    0.4125 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7672    3.4546    0.9687 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.6884    3.8684    2.4260 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6331    4.7179    0.1541 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7868    3.9598    0.0868 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.0295    3.0273   -1.0621 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4221    1.6726   -0.5050 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.1786    1.7454    0.7700 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3555    1.0317   -1.5403 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9424   -0.4222   -1.6246 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9122   -0.6089   -0.4982 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.6455   -0.8951    0.6414 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0935   -1.7883   -0.8532 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.3432   -1.6885   -2.1480 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0618   -2.9712   -1.0187 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2613    0.7144   -0.4955 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.9512   -2.0659    2.6383 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0949   -2.8681    2.5338 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8018   -2.9857    1.3561 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9428   -3.7880    1.2579 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5443   -1.9272   -2.2850 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6305   -0.5859   -1.7648 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2651   -1.8638   -2.9431 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9167   -0.9681   -0.5182 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6950    0.9484    1.6115 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1260    2.5156    1.0154 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4743    2.6084   -0.6285 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4380    4.6969    2.5479 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3421    4.2258    2.6274 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9759    2.9923    3.0411 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6720    4.4608    0.5120 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8951    3.4117   -1.6482 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1979    2.9135   -1.7540 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6125    1.6303    1.6861 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0171    0.9895    0.8131 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7089    2.7354    0.8360 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4111    1.0731   -1.2092 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2810    1.5463   -2.5114 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7998   -1.1106   -1.4940 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4472   -0.5462   -2.6110 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1236   -1.2376    1.3902 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3822   -2.1213   -0.0770 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4024   -2.5384   -2.1466 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0312   -1.9577   -3.0020 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1946   -0.7559   -2.3053 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4188   -2.9785   -2.0572 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5377   -3.9380   -0.8337 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9176   -2.8802   -0.3316 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7379    0.8500   -1.4696 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4372   -2.0154    3.5979 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4623   -3.4318    3.4006 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3113   -4.3149    2.0143 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3 28  2  0
 28 29  1  0
 28 27  1  0
 27 26  2  0
 26  5  1  0
  5  4  2  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  1
 11 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  1
 16 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  1
 20 22  1  0
 22 23  1  0
 22 24  1  0
 20 25  1  0
  4  3  1  0
 25  9  1  0
 14 11  1  0
 25 16  1  0
  1 30  1  0
  1 31  1  0
  1 32  1  0
 29 61  1  0
 27 60  1  0
 26 59  1  0
  4 33  1  0
  9 34  1  1
 10 35  1  0
 10 36  1  0
 12 37  1  0
 12 38  1  0
 12 39  1  0
 14 40  1  1
 15 41  1  0
 15 42  1  0
 17 43  1  0
 17 44  1  0
 17 45  1  0
 18 46  1  0
 18 47  1  0
 19 48  1  0
 19 49  1  0
 21 50  1  0
 22 51  1  1
 23 52  1  0
 23 53  1  0
 23 54  1  0
 24 55  1  0
 24 56  1  0
 24 57  1  0
 25 58  1  6
M  END


  Mrv1652304282210402D          

 29 32  0  0  1  0            999 V2000
    3.6631    1.1824    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.8226    0.3730    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.2892   -0.2564    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.4645   -0.2317    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9696    0.4283    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.1771    1.2268    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.9308    1.5624    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3819    1.0073    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3484   -0.1145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6248   -1.0100    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1399   -1.6775    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3194   -1.5913    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4755   -2.4311    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2960   -2.5173    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6316   -3.2710    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1467   -3.9384    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3262   -3.8523    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9906   -3.0986    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4823   -4.6921    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4521   -3.3572    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7877   -4.1108    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6417    0.2746    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.9884    1.0232    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3836    1.5843    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3454   -0.1559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0701    0.2383    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3245   -0.9807    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6380   -0.5504    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6507    2.0073    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  6  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  1  7  1  0  0  0  0
  6  8  1  1  0  0  0
  5  8  1  0  0  0  0
  5  9  1  6  0  0  0
  3 10  1  1  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 11 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 13 18  1  0  0  0  0
 16 19  1  0  0  0  0
 15 20  1  0  0  0  0
 20 21  1  0  0  0  0
  2 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
  1 24  1  0  0  0  0
 22 25  1  1  0  0  0
 25 26  1  0  0  0  0
 25 27  1  0  0  0  0
 22 28  1  6  0  0  0
  1 29  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0064440

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=C(O)C=CC(=C1)C(=O)O[C@H]1C[C@@]2(C)O[C@H]2C[C@@]2(C)CC[C@@](O)(C(C)C)[C@H]12

> <INCHI_IDENTIFIER>
InChI=1S/C23H32O6/c1-13(2)23(26)9-8-21(3)12-18-22(4,29-18)11-17(19(21)23)28-20(25)14-6-7-15(24)16(10-14)27-5/h6-7,10,13,17-19,24,26H,8-9,11-12H2,1-5H3/t17-,18-,19+,21+,22+,23+/m0/s1

> <INCHI_KEY>
LUXHNMNHDPKHBY-CNAOLAIUSA-N

> <FORMULA>
C23H32O6

> <MOLECULAR_WEIGHT>
404.503

> <EXACT_MASS>
404.21988875

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
61

> <JCHEM_AVERAGE_POLARIZABILITY>
43.58097364718073

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1aS,2aR,5R,5aS,6S,7aR)-5-hydroxy-2a,7a-dimethyl-5-(propan-2-yl)-decahydroazuleno[5,6-b]oxiren-6-yl 4-hydroxy-3-methoxybenzoate

> <ALOGPS_LOGP>
3.44

> <JCHEM_LOGP>
3.422981384666667

> <ALOGPS_LOGS>
-4.56

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.270174837614931

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.99050278380484

> <JCHEM_PKA_STRONGEST_BASIC>
-3.11802652371464

> <JCHEM_POLAR_SURFACE_AREA>
88.52000000000001

> <JCHEM_REFRACTIVITY>
107.7567

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.12e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1aS,2aR,5R,5aS,6S,7aR)-5-hydroxy-5-isopropyl-2a,7a-dimethyl-hexahydro-1aH-azuleno[5,6-b]oxiren-6-yl 4-hydroxy-3-methoxybenzoate

> <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       6.838   2.207   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       7.135   0.696   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       6.140  -0.479   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       4.600  -0.433   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       3.677   0.800   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.064   2.290   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       5.471   2.917   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       2.579   1.880   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       2.517  -0.214   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       6.766  -1.885   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       5.861  -3.131   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       4.330  -2.970   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       6.488  -4.538   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       8.019  -4.699   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       8.646  -6.106   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       7.741  -7.352   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       6.209  -7.191   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       5.582  -5.784   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       8.367  -8.759   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0      10.177  -6.267   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0      10.804  -7.674   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       8.664   0.513   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       9.312   1.910   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       8.183   2.957   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       9.978  -0.291   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      11.331   0.445   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       9.939  -1.831   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0       8.658  -1.027   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0       6.815   3.747   0.000  0.00  0.00           C+0
CONECT    1    2    7   24   29                                             
CONECT    2    1    3   22                                                  
CONECT    3    2    4   10                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6    8    9                                             
CONECT    6    5    7    8                                                  
CONECT    7    6    1                                                       
CONECT    8    6    5                                                       
CONECT    9    5                                                            
CONECT   10    3   11                                                       
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14   18                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16   20                                                  
CONECT   16   15   17   19                                                  
CONECT   17   16   18                                                       
CONECT   18   17   13                                                       
CONECT   19   16                                                            
CONECT   20   15   21                                                       
CONECT   21   20                                                            
CONECT   22    2   23   25   28                                             
CONECT   23   22   24                                                       
CONECT   24   23    1                                                       
CONECT   25   22   26   27                                                  
CONECT   26   25                                                            
CONECT   27   25                                                            
CONECT   28   22                                                            
CONECT   29    1                                                            
MASTER        0    0    0    0    0    0    0    0   29    0   64    0
END

View in JSmol

Synonyms

Value	Source
(1AS,2ar,5R,5as,6S,7ar)-5-hydroxy-2a,7a-dimethyl-5-(propan-2-yl)-decahydroazuleno[5,6-b]oxiren-6-yl 4-hydroxy-3-methoxybenzoic acid	Generator

Chemical Formula

C₂₃H₃₂O₆

Average Mass

404.5030 Da

Monoisotopic Mass

404.21989 Da

IUPAC Name

(1aS,2aR,5R,5aS,6S,7aR)-5-hydroxy-2a,7a-dimethyl-5-(propan-2-yl)-decahydroazuleno[5,6-b]oxiren-6-yl 4-hydroxy-3-methoxybenzoate

Traditional Name

(1aS,2aR,5R,5aS,6S,7aR)-5-hydroxy-5-isopropyl-2a,7a-dimethyl-hexahydro-1aH-azuleno[5,6-b]oxiren-6-yl 4-hydroxy-3-methoxybenzoate

CAS Registry Number

Not Available

SMILES

COC1=C(O)C=CC(=C1)C(=O)O[C@H]1C[C@@]2(C)O[C@H]2C[C@@]2(C)CC[C@@](O)(C(C)C)[C@H]12

InChI Identifier

InChI=1S/C23H32O6/c1-13(2)23(26)9-8-21(3)12-18-22(4,29-18)11-17(19(21)23)28-20(25)14-6-7-15(24)16(10-14)27-5/h6-7,10,13,17-19,24,26H,8-9,11-12H2,1-5H3/t17-,18-,19+,21+,22+,23+/m0/s1

InChI Key

LUXHNMNHDPKHBY-CNAOLAIUSA-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
Ferula hermonis	LOTUS Database	35616633
Ferula orientalis	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as m-methoxybenzoic acids and derivatives. These are benzoic acids in which the hydrogen atom at position 3 of the benzene ring is replaced by a methoxy group.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Benzoic acids and derivatives

Direct Parent

M-methoxybenzoic acids and derivatives

Alternative Parents

Substituents

P-hydroxybenzoic acid alkyl ester
P-hydroxybenzoic acid ester
M-methoxybenzoic acid or derivatives
Benzoate ester
Methoxyphenol
Phenoxy compound
Anisole
Benzoyl
Methoxybenzene
Phenol ether
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
Phenol
Tertiary alcohol
Cyclic alcohol
Carboxylic acid ester
Oxacycle
Carboxylic acid derivative
Organoheterocyclic compound
Dialkyl ether
Oxirane
Ether
Monocarboxylic acid or derivatives
Organic oxide
Organooxygen compound
Hydrocarbon derivative
Alcohol
Organic oxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	3.44	ALOGPS
logP	3.42	ChemAxon
logS	-4.6	ALOGPS
pKa (Strongest Acidic)	8.99	ChemAxon
pKa (Strongest Basic)	-3.1	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	88.52 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	107.76 m³·mol⁻¹	ChemAxon
Polarizability	43.58 Å³	ChemAxon
Number of Rings	4	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

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

13992122

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for 2,3-Epoxyjaeschkeanadiol 5alpha-vanillate (NP0064440)

MOL for NP0064440 (2,3-Epoxyjaeschkeanadiol 5alpha-vanillate)

3D MOL for NP0064440 (2,3-Epoxyjaeschkeanadiol 5alpha-vanillate)

3D SDF for NP0064440 (2,3-Epoxyjaeschkeanadiol 5alpha-vanillate)

3D-SDF for NP0064440 (2,3-Epoxyjaeschkeanadiol 5alpha-vanillate)

PDB for NP0064440 (2,3-Epoxyjaeschkeanadiol 5alpha-vanillate)

3D PDB for NP0064440 (2,3-Epoxyjaeschkeanadiol 5alpha-vanillate)

SMILES for NP0064440 (2,3-Epoxyjaeschkeanadiol 5alpha-vanillate)

INCHI for NP0064440 (2,3-Epoxyjaeschkeanadiol 5alpha-vanillate)

Structure for NP0064440 (2,3-Epoxyjaeschkeanadiol 5alpha-vanillate)

3D Structure for NP0064440 (2,3-Epoxyjaeschkeanadiol 5alpha-vanillate)