NP-MRD: Showing NP-Card for (1's,3as,4'r,6r,6'r,8's,12'r)-2-ethoxy-3,3a-dihydroxy-1',6',8'-trimethyl-tetrahydro-2h-3'-oxaspiro[furo[2,3-b]pyran-6,7'-tricyclo[6.3.1.0⁴,¹²]dodecan]-2'-one (NP0272471)

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Record Information

Version

2.0

Created at

2022-09-08 19:06:33 UTC

Updated at

2022-09-08 19:06:33 UTC

NP-MRD ID

NP0272471

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1's,3as,4'r,6r,6'r,8's,12'r)-2-ethoxy-3,3a-dihydroxy-1',6',8'-trimethyl-tetrahydro-2h-3'-oxaspiro[furo[2,3-b]pyran-6,7'-tricyclo[6.3.1.0⁴,¹²]dodecan]-2'-one

Description

Marrulibacetal belongs to the class of organic compounds known as o-glycosyl compounds. These are glycoside in which a sugar group is bonded through one carbon to another group via a O-glycosidic bond. (1's,3as,4'r,6r,6'r,8's,12'r)-2-ethoxy-3,3a-dihydroxy-1',6',8'-trimethyl-tetrahydro-2h-3'-oxaspiro[furo[2,3-b]pyran-6,7'-tricyclo[6.3.1.0⁴,¹²]dodecan]-2'-one is found in Marrubium globosum. (1's,3as,4'r,6r,6'r,8's,12'r)-2-ethoxy-3,3a-dihydroxy-1',6',8'-trimethyl-tetrahydro-2h-3'-oxaspiro[furo[2,3-b]pyran-6,7'-tricyclo[6.3.1.0⁴,¹²]dodecan]-2'-one was first documented in 2009 (PMID: 19650652). Based on a literature review a small amount of articles have been published on Marrulibacetal (PMID: 32244661) (PMID: 21924316) (PMID: 34471010) (PMID: 27341320).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309082221062D          

 29 33  0  0  1  0            999 V2000
    5.8516   -1.2958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4001   -0.6795    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1407    0.1036    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3328    0.2705    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7228   -0.2850    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0060    0.1234    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2229   -0.1360    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6066    0.4125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.7735    1.2204    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5567    1.4799    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1729    0.9313    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.4234    1.7174    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9929    1.0223    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4013    1.7391    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4397   -0.3954    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.0559   -0.9440    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6566   -0.6549    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0403   -0.1063    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.2203   -0.1973    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1195    0.5545    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9275    0.7214    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4904    1.1100    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.2652    1.4413    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4857    1.9350    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1978    2.3516    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9146    1.9432    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9904    0.9610    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.5801    1.5379    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2072    0.7016    0.0000 C   0  0  1  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  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
  8  7  1  6  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
  6 11  1  0  0  0  0
 11 12  1  1  0  0  0
 11 13  1  0  0  0  0
  4 13  1  0  0  0  0
 13 14  1  0  0  0  0
  8 15  1  0  0  0  0
 15 16  1  6  0  0  0
 15 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  1  0  0  0
 19 20  1  0  0  0  0
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 20 22  1  0  0  0  0
 22 23  1  6  0  0  0
 22 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
  8 27  1  0  0  0  0
 27 28  1  1  0  0  0
 27 29  1  0  0  0  0
 29 18  1  1  0  0  0
 22 29  1  0  0  0  0
M  END

     RDKit          3D

 63 67  0  0  0  0  0  0  0  0999 V2000
    4.6786   -2.8629   -1.7388 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2318   -2.4115   -0.3692 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4226   -1.2891   -0.4217 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0479   -0.9251    0.8475 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.6991   -0.9084    1.0616 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2903    0.3411    1.4694 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0101    0.6553    1.2210 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3765    1.1017   -0.0108 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.6953    1.4583   -0.9538 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0486    1.7227   -0.4168 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3207    1.3002    0.9746 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.5297    2.3832    1.8495 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5932    0.4543    1.1074 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.5703    0.8434    0.2225 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2758    2.3234    0.2812 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.4359    3.4727    0.8574 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3605    2.0458    1.2432 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9131    0.6916    1.3165 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.2564    0.5543    0.8241 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3605   -0.6041    0.0772 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3129   -0.8786   -0.6782 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1777   -1.4157    0.3368 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.4328   -2.1282    1.6760 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8067   -2.4143   -0.6872 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8620   -2.0169   -1.7286 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8612   -0.9548   -1.4275 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4239    0.1422   -0.5992 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.3769    0.9068   -1.5238 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1439   -0.3786    0.6053 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.6079   -3.9646   -1.8726 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0355   -2.4271   -2.5464 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7376   -2.5757   -1.9284 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1447   -2.2324    0.2581 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7190   -3.2761    0.1205 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4992   -1.6350    1.5756 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4070    0.3322    2.5988 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8069    0.7199   -1.7879 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3646    2.3976   -1.4936 H   0  0  0  0  0  0  0  0  0  0  0  0
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    2.3325    2.8164   -0.4882 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5581    3.2505    1.3443 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9207    0.4978    2.1666 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2280    1.3975    0.7465 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6121    2.7455   -0.7052 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2007    4.2965    0.9982 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0728    3.2472    1.8567 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2805    3.8692    0.1422 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0462    2.3792    2.2780 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2087    2.7572    1.0067 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9949    0.3494    2.3924 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9405   -1.4698    2.3847 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4270   -2.3662    2.0794 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0285   -3.0469    1.5152 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7679   -2.7926   -1.1484 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4112   -3.3270   -0.1482 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4527   -1.7962   -2.6712 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2674   -2.9313   -2.0412 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0724   -1.3929   -1.0902 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6341   -0.5052   -2.4460 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1529    1.4607   -1.0096 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8011    1.4667   -2.2790 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9181    0.1061   -2.1116 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3901   -0.7988    1.2947 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
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 25 26  1  0
 26 27  1  0
 27 28  1  6
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 13  4  1  0
 29 18  1  0
 11  6  1  0
 29 22  1  0
 27  8  1  0
  1 30  1  0
  1 31  1  0
  1 32  1  0
  2 33  1  0
  2 34  1  0
  4 35  1  1
  6 36  1  1
  9 37  1  0
  9 38  1  0
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 28 60  1  0
 28 61  1  0
 28 62  1  0
 29 63  1  1
M  END


  Mrv1652309082221062D          

 29 33  0  0  1  0            999 V2000
    5.8516   -1.2958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4001   -0.6795    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1407    0.1036    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3328    0.2705    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7228   -0.2850    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0060    0.1234    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2229   -0.1360    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6066    0.4125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.7735    1.2204    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5567    1.4799    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1729    0.9313    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.4234    1.7174    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9929    1.0223    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4013    1.7391    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4397   -0.3954    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.0559   -0.9440    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6566   -0.6549    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0403   -0.1063    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.2203   -0.1973    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1195    0.5545    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9275    0.7214    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4904    1.1100    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.2652    1.4413    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4857    1.9350    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1978    2.3516    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9146    1.9432    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9904    0.9610    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.5801    1.5379    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2072    0.7016    0.0000 C   0  0  1  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  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
  8  7  1  6  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
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  6 11  1  0  0  0  0
 11 12  1  1  0  0  0
 11 13  1  0  0  0  0
  4 13  1  0  0  0  0
 13 14  1  0  0  0  0
  8 15  1  0  0  0  0
 15 16  1  6  0  0  0
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 17 18  1  0  0  0  0
 18 19  1  1  0  0  0
 19 20  1  0  0  0  0
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 20 22  1  0  0  0  0
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 27 29  1  0  0  0  0
 29 18  1  1  0  0  0
 22 29  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0272471

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCOC1OC2O[C@]3(CC[C@]2(O)C1O)[C@H](C)C[C@H]1OC(=O)[C@@]2(C)CCC[C@@]3(C)[C@@H]12

> <INCHI_IDENTIFIER>
InChI=1S/C22H34O7/c1-5-26-16-15(23)21(25)9-10-22(29-18(21)28-16)12(2)11-13-14-19(3,17(24)27-13)7-6-8-20(14,22)4/h12-16,18,23,25H,5-11H2,1-4H3/t12-,13-,14+,15?,16?,18?,19+,20+,21+,22-/m1/s1

> <INCHI_KEY>
ROLCCWPTXCTWNC-NVKDOJEFSA-N

> <FORMULA>
C22H34O7

> <MOLECULAR_WEIGHT>
410.507

> <EXACT_MASS>
410.230453435

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
63

> <JCHEM_AVERAGE_POLARIZABILITY>
43.60555672358544

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1'S,3aS,4'R,6R,6'R,8'S,12'R)-2-ethoxy-3,3a-dihydroxy-1',6',8'-trimethyl-hexahydro-3'-oxaspiro[furo[2,3-b]pyran-6,7'-tricyclo[6.3.1.0^{4,12}]dodecane]-2'-one

> <JCHEM_LOGP>
2.614415281333332

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.154273490452194

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.76722931618084

> <JCHEM_PKA_STRONGEST_BASIC>
-3.938345870001339

> <JCHEM_POLAR_SURFACE_AREA>
94.45000000000002

> <JCHEM_REFRACTIVITY>
101.7446

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(1'S,3aS,4'R,6R,6'R,8'S,12'R)-2-ethoxy-3,3a-dihydroxy-1',6',8'-trimethyl-tetrahydro-2H-3'-oxaspiro[furo[2,3-b]pyran-6,7'-tricyclo[6.3.1.0^{4,12}]dodecane]-2'-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 08-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   08-SEP-22         0                                  
HETATM    1  C   UNK     0      10.923  -2.419   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      11.947  -1.268   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0      11.463   0.193   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0       9.954   0.505   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0       8.816  -0.532   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       7.478   0.230   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       6.016  -0.254   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       4.866   0.770   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.177   2.278   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       6.639   2.762   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       7.789   1.738   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       8.257   3.206   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       9.320   1.908   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0      10.082   3.246   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       4.554  -0.738   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       5.704  -1.762   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       3.092  -1.222   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       1.942  -0.198   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       0.411  -0.368   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0      -0.223   1.035   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      -1.731   1.347   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       0.915   2.072   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -0.495   2.690   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       0.907   3.612   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       2.236   4.390   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       3.574   3.627   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       3.715   1.794   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       4.816   2.871   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       2.253   1.310   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5   13                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7   11                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   15   27                                             
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10    6   12   13                                             
CONECT   12   11                                                            
CONECT   13   11    4   14                                                  
CONECT   14   13                                                            
CONECT   15    8   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15   18                                                       
CONECT   18   17   19   29                                                  
CONECT   19   18   20                                                       
CONECT   20   19   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20   23   24   29                                             
CONECT   23   22                                                            
CONECT   24   22   25                                                       
CONECT   25   24   26                                                       
CONECT   26   25   27                                                       
CONECT   27   26    8   28   29                                             
CONECT   28   27                                                            
CONECT   29   27   18   22                                                  
MASTER        0    0    0    0    0    0    0    0   29    0   66    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₂H₃₄O₇

Average Mass

410.5070 Da

Monoisotopic Mass

410.23045 Da

IUPAC Name

(1'S,3aS,4'R,6R,6'R,8'S,12'R)-2-ethoxy-3,3a-dihydroxy-1',6',8'-trimethyl-hexahydro-3'-oxaspiro[furo[2,3-b]pyran-6,7'-tricyclo[6.3.1.0^{4,12}]dodecane]-2'-one

Traditional Name

(1'S,3aS,4'R,6R,6'R,8'S,12'R)-2-ethoxy-3,3a-dihydroxy-1',6',8'-trimethyl-tetrahydro-2H-3'-oxaspiro[furo[2,3-b]pyran-6,7'-tricyclo[6.3.1.0^{4,12}]dodecane]-2'-one

CAS Registry Number

Not Available

SMILES

CCOC1OC2O[C@]3(CC[C@]2(O)C1O)[C@H](C)C[C@H]1OC(=O)[C@@]2(C)CCC[C@@]3(C)[C@@H]12

InChI Identifier

InChI=1S/C22H34O7/c1-5-26-16-15(23)21(25)9-10-22(29-18(21)28-16)12(2)11-13-14-19(3,17(24)27-13)7-6-8-20(14,22)4/h12-16,18,23,25H,5-11H2,1-4H3/t12-,13-,14+,15?,16?,18?,19+,20+,21+,22-/m1/s1

InChI Key

ROLCCWPTXCTWNC-NVKDOJEFSA-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
Marrubium globosum	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as o-glycosyl compounds. These are glycoside in which a sugar group is bonded through one carbon to another group via a O-glycosidic bond.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbohydrates and carbohydrate conjugates

Direct Parent

O-glycosyl compounds

Alternative Parents

Substituents

O-glycosyl compound
Furopyran
Pyran
Oxane
Monosaccharide
Gamma butyrolactone
Tetrahydrofuran
Tertiary alcohol
Furan
Secondary alcohol
Lactone
Carboxylic acid ester
1,2-diol
Oxacycle
Organoheterocyclic compound
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Acetal
Organic oxide
Hydrocarbon derivative
Carbonyl group
Alcohol
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental Properties

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

Predicted Properties

Property	Value	Source
logP	2.61	ChemAxon
pKa (Strongest Acidic)	11.77	ChemAxon
pKa (Strongest Basic)	-3.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	94.45 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	101.74 m³·mol⁻¹	ChemAxon
Polarizability	43.61 Å³	ChemAxon
Number of Rings	5	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

102597519

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Sakagami Y, Kondo N, Sawayama Y, Yamakoshi H, Nakamura S: Total Syntheses of Marrubiin and Related Labdane Diterpene Lactones. Molecules. 2020 Apr 1;25(7). pii: molecules25071610. doi: 10.3390/molecules25071610. [PubMed:32244661 ]
Zaabat N, Hay AE, Michalet S, Darbour N, Bayet C, Skandrani I, Chekir-Ghedira L, Akkal S, Dijoux-Franca MG: Antioxidant and antigenotoxic properties of compounds isolated from Marrubium deserti de Noe. Food Chem Toxicol. 2011 Dec;49(12):3328-35. doi: 10.1016/j.fct.2011.08.026. Epub 2011 Sep 6. [PubMed:21924316 ]
Rigano D, Aviello G, Bruno M, Formisano C, Rosselli S, Capasso R, Senatore F, Izzo AA, Borrelli F: Antispasmodic effects and structure-activity relationships of labdane diterpenoids from Marrubium globosum ssp. libanoticum. J Nat Prod. 2009 Aug;72(8):1477-81. doi: 10.1021/np9002756. [PubMed:19650652 ]
Yamakoshi H: [Studies on the Syntheses of Bioactive Natural Products Having a Fused Ring System Based on Novel Skeletal Construction Methods]. Yakugaku Zasshi. 2021;141(9):1087-1094. doi: 10.1248/yakushi.21-00126. [PubMed:34471010 ]
Yamakoshi H, Sawayama Y, Akahori Y, Kato M, Nakamura S: Total Syntheses of (+)-Marrubiin and (-)-Marrulibacetal. Org Lett. 2016 Jul 15;18(14):3430-3. doi: 10.1021/acs.orglett.6b01602. Epub 2016 Jun 24. [PubMed:27341320 ]
LOTUS database [Link]

Showing NP-Card for (1's,3as,4'r,6r,6'r,8's,12'r)-2-ethoxy-3,3a-dihydroxy-1',6',8'-trimethyl-tetrahydro-2h-3'-oxaspiro[furo[2,3-b]pyran-6,7'-tricyclo[6.3.1.0⁴,¹²]dodecan]-2'-one (NP0272471)

MOL for NP0272471 ((1's,3as,4'r,6r,6'r,8's,12'r)-2-ethoxy-3,3a-dihydroxy-1',6',8'-trimethyl-tetrahydro-2h-3'-oxaspiro[furo[2,3-b]pyran-6,7'-tricyclo[6.3.1.0⁴,¹²]dodecan]-2'-one)

3D MOL for NP0272471 ((1's,3as,4'r,6r,6'r,8's,12'r)-2-ethoxy-3,3a-dihydroxy-1',6',8'-trimethyl-tetrahydro-2h-3'-oxaspiro[furo[2,3-b]pyran-6,7'-tricyclo[6.3.1.0⁴,¹²]dodecan]-2'-one)

3D SDF for NP0272471 ((1's,3as,4'r,6r,6'r,8's,12'r)-2-ethoxy-3,3a-dihydroxy-1',6',8'-trimethyl-tetrahydro-2h-3'-oxaspiro[furo[2,3-b]pyran-6,7'-tricyclo[6.3.1.0⁴,¹²]dodecan]-2'-one)

3D-SDF for NP0272471 ((1's,3as,4'r,6r,6'r,8's,12'r)-2-ethoxy-3,3a-dihydroxy-1',6',8'-trimethyl-tetrahydro-2h-3'-oxaspiro[furo[2,3-b]pyran-6,7'-tricyclo[6.3.1.0⁴,¹²]dodecan]-2'-one)

PDB for NP0272471 ((1's,3as,4'r,6r,6'r,8's,12'r)-2-ethoxy-3,3a-dihydroxy-1',6',8'-trimethyl-tetrahydro-2h-3'-oxaspiro[furo[2,3-b]pyran-6,7'-tricyclo[6.3.1.0⁴,¹²]dodecan]-2'-one)

3D PDB for NP0272471 ((1's,3as,4'r,6r,6'r,8's,12'r)-2-ethoxy-3,3a-dihydroxy-1',6',8'-trimethyl-tetrahydro-2h-3'-oxaspiro[furo[2,3-b]pyran-6,7'-tricyclo[6.3.1.0⁴,¹²]dodecan]-2'-one)

SMILES for NP0272471 ((1's,3as,4'r,6r,6'r,8's,12'r)-2-ethoxy-3,3a-dihydroxy-1',6',8'-trimethyl-tetrahydro-2h-3'-oxaspiro[furo[2,3-b]pyran-6,7'-tricyclo[6.3.1.0⁴,¹²]dodecan]-2'-one)

INCHI for NP0272471 ((1's,3as,4'r,6r,6'r,8's,12'r)-2-ethoxy-3,3a-dihydroxy-1',6',8'-trimethyl-tetrahydro-2h-3'-oxaspiro[furo[2,3-b]pyran-6,7'-tricyclo[6.3.1.0⁴,¹²]dodecan]-2'-one)

Structure for NP0272471 ((1's,3as,4'r,6r,6'r,8's,12'r)-2-ethoxy-3,3a-dihydroxy-1',6',8'-trimethyl-tetrahydro-2h-3'-oxaspiro[furo[2,3-b]pyran-6,7'-tricyclo[6.3.1.0⁴,¹²]dodecan]-2'-one)

3D Structure for NP0272471 ((1's,3as,4'r,6r,6'r,8's,12'r)-2-ethoxy-3,3a-dihydroxy-1',6',8'-trimethyl-tetrahydro-2h-3'-oxaspiro[furo[2,3-b]pyran-6,7'-tricyclo[6.3.1.0⁴,¹²]dodecan]-2'-one)