NP-MRD: Showing NP-Card for (1r,8s,10r,11s,12s,20r)-20-hydroxy-11,12-dimethyl-5,14-dioxo-6,18-dioxapentacyclo[10.7.1.0⁴,⁸.0⁸,²⁰.0¹⁵,¹⁹]icosa-3,15(19),16-trien-10-yl acetate (NP0261693)

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Record Information

Version

2.0

Created at

2022-09-08 04:12:37 UTC

Updated at

2022-09-08 04:12:37 UTC

NP-MRD ID

NP0261693

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1r,8s,10r,11s,12s,20r)-20-hydroxy-11,12-dimethyl-5,14-dioxo-6,18-dioxapentacyclo[10.7.1.0⁴,⁸.0⁸,²⁰.0¹⁵,¹⁹]icosa-3,15(19),16-trien-10-yl acetate

Description

Salvimexicanolide belongs to the class of organic compounds known as cycloheptafurans. These are organic heterocyclic compounds containing a cycloheptane derivative fused to a furan. Furan is a five-membered aromatic ring with four carbon atoms and one oxygen atom. (1r,8s,10r,11s,12s,20r)-20-hydroxy-11,12-dimethyl-5,14-dioxo-6,18-dioxapentacyclo[10.7.1.0⁴,⁸.0⁸,²⁰.0¹⁵,¹⁹]icosa-3,15(19),16-trien-10-yl acetate is found in Salvia mexicana. (1r,8s,10r,11s,12s,20r)-20-hydroxy-11,12-dimethyl-5,14-dioxo-6,18-dioxapentacyclo[10.7.1.0⁴,⁸.0⁸,²⁰.0¹⁵,¹⁹]icosa-3,15(19),16-trien-10-yl acetate was first documented in 2011 (PMID: 22019574). Based on a literature review very few articles have been published on Salvimexicanolide.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309082206122D          

 29 33  0  0  1  0            999 V2000
   -1.5894   -3.2929    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0096   -2.7060    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2279   -1.9104    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2114   -2.9148    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3684   -2.3280    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.1515   -1.7657    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7300   -0.9455    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0408   -1.3990    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6034   -0.8836    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3124   -0.1117    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7658    0.5775    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5117   -0.1499    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0916    0.4369    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8898    0.2282    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1080   -0.5674    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.9284   -0.6549    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4533   -0.0185    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2208   -0.3210    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1703   -1.1445    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3715   -1.3508    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1037   -2.1311    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6905   -2.7110    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3266   -2.4083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6254   -1.9735    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.7618   -2.7872    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1666   -2.5367    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4227   -3.3210    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5282   -1.1543    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.3085   -1.4221    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  2  4  1  0  0  0  0
  5  4  1  6  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  6  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 10 12  1  0  0  0  0
  7 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  1  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 19 20  1  0  0  0  0
 16 20  2  0  0  0  0
 20 21  1  0  0  0  0
 21 22  2  0  0  0  0
 21 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  6  0  0  0
 24 26  1  0  0  0  0
  5 26  1  0  0  0  0
 26 27  1  6  0  0  0
 24 28  1  0  0  0  0
 15 28  1  0  0  0  0
  7 28  1  0  0  0  0
 28 29  1  6  0  0  0
M  END

     RDKit          3D

 53 57  0  0  0  0  0  0  0  0999 V2000
    5.0691   -0.3206    1.3235 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2183   -0.0815    0.1281 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7593    0.0151   -1.0057 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8370    0.0437    0.1904 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0020    0.2675   -0.9003 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.2301    1.5129   -0.9307 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1152    1.5858    0.0910 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7974    2.0703    1.3740 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0891    3.4523    1.1081 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3206    3.9231    0.0577 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3277    5.0388   -0.5111 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5901    2.8148   -0.3260 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7621    2.7830   -0.8897 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4016    1.4598   -1.1110 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1027    0.7008    0.1890 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.1268   -0.2259    0.6121 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2028    0.0690    1.3459 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9248   -0.9714    1.5562 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3429   -2.0587    0.9481 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1924   -1.5851    0.3430 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2230   -2.3434   -0.4325 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3858   -3.5890   -0.4238 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1035   -1.7380   -1.1974 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1737   -0.8983   -0.3491 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.2273   -1.9400    0.7331 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0650   -0.8466   -1.2068 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.8996   -2.1090   -1.1303 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6628    0.3223    0.2852 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.5171    0.0784    1.6995 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3739    0.6398    1.8017 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5986   -1.0214    2.0378 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0037   -0.8390    0.9698 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7007    0.3179   -1.7983 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7889    1.6170   -1.9633 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8757    2.3783   -0.7620 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7693    1.5779    1.5184 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1889    1.9494    2.2673 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2693    3.6888   -1.1944 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5080    1.5763   -1.1352 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9869    1.0048   -1.9987 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1850    1.5401    0.9686 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8384   -1.0067    2.1143 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6751   -3.0992    0.9171 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4202   -1.2772   -2.1353 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4962   -2.6360   -1.5189 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0293   -1.5660    1.3638 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6944   -1.9928    1.3840 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3524   -2.9334    0.3075 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7853   -0.7432   -2.2975 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4962   -2.9698   -1.6501 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2484   -2.3105   -0.0905 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8551   -1.8531   -1.6814 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2386    0.5279    2.1870 H   0  0  0  0  0  0  0  0  0  0  0  0
 27 26  1  0
 26  5  1  0
  5  6  1  0
  7  6  1  6
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 10 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 20  2  0
 20 19  1  0
 19 18  2  0
 18 17  1  0
 20 21  1  0
 21 22  2  0
 21 23  1  0
 23 24  1  0
 24 25  1  1
 24 28  1  0
 28 29  1  1
  5  4  1  0
  4  2  1  0
  2  1  1  0
  2  3  2  0
 24 26  1  0
 12  7  1  0
 28 15  1  0
 28  7  1  0
 17 16  1  0
 27 50  1  0
 27 51  1  0
 27 52  1  0
 26 49  1  6
  5 33  1  6
  6 34  1  0
  6 35  1  0
  8 36  1  0
  8 37  1  0
 13 38  1  0
 14 39  1  0
 14 40  1  0
 15 41  1  1
 19 43  1  0
 18 42  1  0
 23 44  1  0
 23 45  1  0
 25 46  1  0
 25 47  1  0
 25 48  1  0
 29 53  1  0
  1 30  1  0
  1 31  1  0
  1 32  1  0
M  END


  Mrv1652309082206122D          

 29 33  0  0  1  0            999 V2000
   -1.5894   -3.2929    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0096   -2.7060    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2279   -1.9104    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2114   -2.9148    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3684   -2.3280    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.1515   -1.7657    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7300   -0.9455    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0408   -1.3990    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6034   -0.8836    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3124   -0.1117    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7658    0.5775    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5117   -0.1499    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0916    0.4369    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8898    0.2282    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1080   -0.5674    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.9284   -0.6549    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4533   -0.0185    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2208   -0.3210    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1703   -1.1445    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3715   -1.3508    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1037   -2.1311    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6905   -2.7110    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3266   -2.4083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6254   -1.9735    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.7618   -2.7872    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1666   -2.5367    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4227   -3.3210    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5282   -1.1543    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.3085   -1.4221    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  2  4  1  0  0  0  0
  5  4  1  6  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  6  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 10 12  1  0  0  0  0
  7 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  1  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 19 20  1  0  0  0  0
 16 20  2  0  0  0  0
 20 21  1  0  0  0  0
 21 22  2  0  0  0  0
 21 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  6  0  0  0
 24 26  1  0  0  0  0
  5 26  1  0  0  0  0
 26 27  1  6  0  0  0
 24 28  1  0  0  0  0
 15 28  1  0  0  0  0
  7 28  1  0  0  0  0
 28 29  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0261693

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@@H]1[C@@H](C[C@@]23COC(=O)C2=CC[C@H]2C4=C(C=CO4)C(=O)C[C@]1(C)[C@@]32O)OC(C)=O

> <INCHI_IDENTIFIER>
InChI=1S/C22H24O7/c1-11-17(29-12(2)23)9-21-10-28-19(25)15(21)5-4-14-18-13(6-7-27-18)16(24)8-20(11,3)22(14,21)26/h5-7,11,14,17,26H,4,8-10H2,1-3H3/t11-,14+,17-,20+,21-,22-/m1/s1

> <INCHI_KEY>
QPELONIXWRZFNT-MXYYJSRBSA-N

> <FORMULA>
C22H24O7

> <MOLECULAR_WEIGHT>
400.427

> <EXACT_MASS>
400.152203113

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
53

> <JCHEM_AVERAGE_POLARIZABILITY>
39.76585669541621

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1R,8S,10R,11S,12S,20R)-20-hydroxy-11,12-dimethyl-5,14-dioxo-6,18-dioxapentacyclo[10.7.1.0^{4,8}.0^{8,20}.0^{15,19}]icosa-3,15(19),16-trien-10-yl acetate

> <JCHEM_LOGP>
1.0101207093333329

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
15.353365429170218

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.317794892507983

> <JCHEM_PKA_STRONGEST_BASIC>
-2.9853897801170404

> <JCHEM_POLAR_SURFACE_AREA>
103.04

> <JCHEM_REFRACTIVITY>
100.70499999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(1R,8S,10R,11S,12S,20R)-20-hydroxy-11,12-dimethyl-5,14-dioxo-6,18-dioxapentacyclo[10.7.1.0^{4,8}.0^{8,20}.0^{15,19}]icosa-3,15(19),16-trien-10-yl acetate

> <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      -2.967  -6.147   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.885  -5.051   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0      -2.292  -3.566   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0      -0.395  -5.441   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       0.688  -4.346   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.283  -3.296   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.363  -1.765   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.076  -2.611   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0      -1.126  -1.649   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0      -0.583  -0.208   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      -1.430   1.078   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       0.955  -0.280   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       2.038   0.816   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       3.528   0.426   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       3.935  -1.059   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       5.466  -1.223   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       6.446  -0.034   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       7.879  -0.599   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       7.784  -2.136   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       6.293  -2.522   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       5.793  -3.978   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       6.889  -5.061   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       4.343  -4.495   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       3.034  -3.684   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       3.289  -5.203   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       2.178  -4.735   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       2.656  -6.199   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       2.853  -2.155   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0       4.309  -2.655   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6   26                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8   12   28                                             
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10    7   13                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16   28                                                  
CONECT   16   15   17   20                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   16   21                                                  
CONECT   21   20   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21   24                                                       
CONECT   24   23   25   26   28                                             
CONECT   25   24                                                            
CONECT   26   24    5   27                                                  
CONECT   27   26                                                            
CONECT   28   24   15    7   29                                             
CONECT   29   28                                                            
MASTER        0    0    0    0    0    0    0    0   29    0   66    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₂H₂₄O₇

Average Mass

400.4270 Da

Monoisotopic Mass

400.15220 Da

IUPAC Name

(1R,8S,10R,11S,12S,20R)-20-hydroxy-11,12-dimethyl-5,14-dioxo-6,18-dioxapentacyclo[10.7.1.0^{4,8}.0^{8,20}.0^{15,19}]icosa-3,15(19),16-trien-10-yl acetate

Traditional Name

(1R,8S,10R,11S,12S,20R)-20-hydroxy-11,12-dimethyl-5,14-dioxo-6,18-dioxapentacyclo[10.7.1.0^{4,8}.0^{8,20}.0^{15,19}]icosa-3,15(19),16-trien-10-yl acetate

CAS Registry Number

Not Available

SMILES

C[C@@H]1[C@@H](C[C@@]23COC(=O)C2=CC[C@H]2C4=C(C=CO4)C(=O)C[C@]1(C)[C@@]32O)OC(C)=O

InChI Identifier

InChI=1S/C22H24O7/c1-11-17(29-12(2)23)9-21-10-28-19(25)15(21)5-4-14-18-13(6-7-27-18)16(24)8-20(11,3)22(14,21)26/h5-7,11,14,17,26H,4,8-10H2,1-3H3/t11-,14+,17-,20+,21-,22-/m1/s1

InChI Key

QPELONIXWRZFNT-MXYYJSRBSA-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
Salvia mexicana	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as cycloheptafurans. These are organic heterocyclic compounds containing a cycloheptane derivative fused to a furan. Furan is a five-membered aromatic ring with four carbon atoms and one oxygen atom.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Cycloheptafurans

Sub Class

Not Available

Direct Parent

Cycloheptafurans

Alternative Parents

Substituents

Cycloheptafuran
Aryl ketone
Aryl alkyl ketone
Dicarboxylic acid or derivatives
Gamma butyrolactone
Cyclic alcohol
Heteroaromatic compound
Furan
Tertiary alcohol
Tetrahydrofuran
Enoate ester
Alpha,beta-unsaturated carboxylic ester
Lactone
Ketone
Carboxylic acid ester
Oxacycle
Carboxylic acid derivative
Carbonyl group
Hydrocarbon derivative
Organooxygen compound
Organic oxide
Organic oxygen compound
Alcohol
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	1.01	ChemAxon
pKa (Strongest Acidic)	13.32	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	103.04 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	100.7 m³·mol⁻¹	ChemAxon
Polarizability	39.77 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

100974953

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Frontana-Uribe BA, Escarcega-Bobadilla MV, Estrada-Reyes R, Morales-Serna JA, Salmon M, Cardenas J: A new languidulane diterpenoid from Salvia mexicana var. mexicana. Molecules. 2011 Oct 21;16(10):8866-73. doi: 10.3390/molecules16108866. [PubMed:22019574 ]
LOTUS database [Link]

Showing NP-Card for (1r,8s,10r,11s,12s,20r)-20-hydroxy-11,12-dimethyl-5,14-dioxo-6,18-dioxapentacyclo[10.7.1.0⁴,⁸.0⁸,²⁰.0¹⁵,¹⁹]icosa-3,15(19),16-trien-10-yl acetate (NP0261693)

MOL for NP0261693 ((1r,8s,10r,11s,12s,20r)-20-hydroxy-11,12-dimethyl-5,14-dioxo-6,18-dioxapentacyclo[10.7.1.0⁴,⁸.0⁸,²⁰.0¹⁵,¹⁹]icosa-3,15(19),16-trien-10-yl acetate)

3D MOL for NP0261693 ((1r,8s,10r,11s,12s,20r)-20-hydroxy-11,12-dimethyl-5,14-dioxo-6,18-dioxapentacyclo[10.7.1.0⁴,⁸.0⁸,²⁰.0¹⁵,¹⁹]icosa-3,15(19),16-trien-10-yl acetate)

3D SDF for NP0261693 ((1r,8s,10r,11s,12s,20r)-20-hydroxy-11,12-dimethyl-5,14-dioxo-6,18-dioxapentacyclo[10.7.1.0⁴,⁸.0⁸,²⁰.0¹⁵,¹⁹]icosa-3,15(19),16-trien-10-yl acetate)

3D-SDF for NP0261693 ((1r,8s,10r,11s,12s,20r)-20-hydroxy-11,12-dimethyl-5,14-dioxo-6,18-dioxapentacyclo[10.7.1.0⁴,⁸.0⁸,²⁰.0¹⁵,¹⁹]icosa-3,15(19),16-trien-10-yl acetate)

PDB for NP0261693 ((1r,8s,10r,11s,12s,20r)-20-hydroxy-11,12-dimethyl-5,14-dioxo-6,18-dioxapentacyclo[10.7.1.0⁴,⁸.0⁸,²⁰.0¹⁵,¹⁹]icosa-3,15(19),16-trien-10-yl acetate)

3D PDB for NP0261693 ((1r,8s,10r,11s,12s,20r)-20-hydroxy-11,12-dimethyl-5,14-dioxo-6,18-dioxapentacyclo[10.7.1.0⁴,⁸.0⁸,²⁰.0¹⁵,¹⁹]icosa-3,15(19),16-trien-10-yl acetate)

SMILES for NP0261693 ((1r,8s,10r,11s,12s,20r)-20-hydroxy-11,12-dimethyl-5,14-dioxo-6,18-dioxapentacyclo[10.7.1.0⁴,⁸.0⁸,²⁰.0¹⁵,¹⁹]icosa-3,15(19),16-trien-10-yl acetate)

INCHI for NP0261693 ((1r,8s,10r,11s,12s,20r)-20-hydroxy-11,12-dimethyl-5,14-dioxo-6,18-dioxapentacyclo[10.7.1.0⁴,⁸.0⁸,²⁰.0¹⁵,¹⁹]icosa-3,15(19),16-trien-10-yl acetate)

Structure for NP0261693 ((1r,8s,10r,11s,12s,20r)-20-hydroxy-11,12-dimethyl-5,14-dioxo-6,18-dioxapentacyclo[10.7.1.0⁴,⁸.0⁸,²⁰.0¹⁵,¹⁹]icosa-3,15(19),16-trien-10-yl acetate)

3D Structure for NP0261693 ((1r,8s,10r,11s,12s,20r)-20-hydroxy-11,12-dimethyl-5,14-dioxo-6,18-dioxapentacyclo[10.7.1.0⁴,⁸.0⁸,²⁰.0¹⁵,¹⁹]icosa-3,15(19),16-trien-10-yl acetate)