NP-MRD: Showing NP-Card for (1r,8r,9r,10s)-3,4,9-trihydroxy-5-isopropyl-11,11-dimethyl-16-oxatetracyclo[6.6.2.0¹,¹⁰.0²,⁷]hexadeca-2(7),3,5-trien-15-one (NP0189968)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-09-04 06:33:34 UTC

Updated at

2022-09-04 06:33:34 UTC

NP-MRD ID

NP0189968

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1r,8r,9r,10s)-3,4,9-trihydroxy-5-isopropyl-11,11-dimethyl-16-oxatetracyclo[6.6.2.0¹,¹⁰.0²,⁷]hexadeca-2(7),3,5-trien-15-one

Description

Isorosmanol belongs to the class of organic compounds known as diterpene lactones. These are diterpenoids containing a lactone moiety. (1r,8r,9r,10s)-3,4,9-trihydroxy-5-isopropyl-11,11-dimethyl-16-oxatetracyclo[6.6.2.0¹,¹⁰.0²,⁷]hexadeca-2(7),3,5-trien-15-one is found in Salvia canariensis, Salvia columbariae, Salvia mellifera, Salvia munzii, Salvia officinalis and Salvia pachyphylla. (1r,8r,9r,10s)-3,4,9-trihydroxy-5-isopropyl-11,11-dimethyl-16-oxatetracyclo[6.6.2.0¹,¹⁰.0²,⁷]hexadeca-2(7),3,5-trien-15-one was first documented in 2009 (PMID: 19711987). Based on a literature review a small amount of articles have been published on isorosmanol (PMID: 25200369) (PMID: 29191008) (PMID: 29048857) (PMID: 27444345).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309042208332D          

 25 28  0  0  1  0            999 V2000
    6.7303   -0.3062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4062    0.4873    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0063    1.0969    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5487    0.6649    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3009    1.4518    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4955    1.6307    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9379    1.0226    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1857    0.2357    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5080   -0.4741    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9911    0.0569    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4272   -0.7123    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9739    0.8569    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.3495    0.2217    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5143    0.0666    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1426    0.8191    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5584    1.5497    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7388    1.8851    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5565    2.4130    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4287    1.5486    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.0148    2.2002    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.8701    3.0750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8639    2.1793    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.5104    1.4067    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6440    0.4897    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0989   -0.3824    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  2  4  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  8 10  2  0  0  0  0
  4 10  1  0  0  0  0
 10 11  1  0  0  0  0
 12  7  1  1  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 16 18  1  0  0  0  0
 19 16  1  6  0  0  0
 12 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  1  0  0  0
 20 22  1  0  0  0  0
  6 22  1  0  0  0  0
 22 23  1  6  0  0  0
 23 24  1  0  0  0  0
 12 24  1  0  0  0  0
 24 25  2  0  0  0  0
M  END

     RDKit          3D

 51 54  0  0  0  0  0  0  0  0999 V2000
    5.3581   -0.1199   -1.2520 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5032    0.5177   -0.1339 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1597    0.8905    1.1054 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1058    0.0532   -0.1735 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1790    0.5932   -1.0785 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8670    0.2981   -1.0317 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3540   -0.5835   -0.0628 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2117   -1.1249    0.8259 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7566   -2.0135    1.8123 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5644   -0.8073    0.7671 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3614   -1.4039    1.6991 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0877   -0.8361   -0.2109 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.7054   -1.9976    0.4596 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2204   -1.8782    0.5810 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6593   -0.5241    1.0940 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2529    0.4698    0.0106 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9607    0.1815   -1.2842 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7607    1.8215    0.4763 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7817    0.4812   -0.0437 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.1950    1.5449   -0.9845 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.6960    2.6216   -0.3081 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1626    0.9382   -1.9234 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.8581   -0.1198   -2.5456 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1693   -1.1609   -1.7028 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4937   -2.2873   -2.1163 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5522   -1.1951   -0.9935 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7435   -0.0932   -2.1663 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3043    0.4153   -1.2819 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3960    1.6133   -0.6811 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0786    0.2534    1.2789 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6056    1.9522    1.0530 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5613    0.8525    2.0401 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5516    1.2707   -1.8237 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3273   -2.4586    2.4821 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3602   -1.3209    1.7487 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3865   -2.2772    1.4693 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5479   -2.9240   -0.1369 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7238   -2.0412   -0.3902 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6169   -2.6537    1.2518 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7452   -0.5280    1.1095 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1510   -0.2211    2.0004 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0027   -0.1523   -0.9797 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5821   -0.6229   -1.8896 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1047    1.1317   -1.8288 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7992    1.6038    0.8653 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1501    2.2587    1.2483 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9121    2.4788   -0.4377 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4618    0.8354    0.9988 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0184    1.9031   -1.6602 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9221    2.6929    0.6439 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2263    1.6720   -2.6034 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  1  0
  8 10  2  0
 10 11  1  0
  7 12  1  0
 12 13  1  1
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 16 18  1  0
 16 19  1  0
 19 20  1  0
 20 21  1  0
 20 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  2  0
 10  4  1  0
 19 12  1  0
 22  6  1  0
 24 12  1  0
  1 26  1  0
  1 27  1  0
  1 28  1  0
  2 29  1  0
  3 30  1  0
  3 31  1  0
  3 32  1  0
  5 33  1  0
  9 34  1  0
 11 35  1  0
 13 36  1  0
 13 37  1  0
 14 38  1  0
 14 39  1  0
 15 40  1  0
 15 41  1  0
 17 42  1  0
 17 43  1  0
 17 44  1  0
 18 45  1  0
 18 46  1  0
 18 47  1  0
 19 48  1  1
 20 49  1  6
 21 50  1  0
 22 51  1  6
M  END


  Mrv1652309042208332D          

 25 28  0  0  1  0            999 V2000
    6.7303   -0.3062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4062    0.4873    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0063    1.0969    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5487    0.6649    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3009    1.4518    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4955    1.6307    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9379    1.0226    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1857    0.2357    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5080   -0.4741    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9911    0.0569    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4272   -0.7123    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9739    0.8569    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.3495    0.2217    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5143    0.0666    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1426    0.8191    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5584    1.5497    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7388    1.8851    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5565    2.4130    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4287    1.5486    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.0148    2.2002    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.8701    3.0750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8639    2.1793    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.5104    1.4067    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6440    0.4897    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0989   -0.3824    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  2  4  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  8 10  2  0  0  0  0
  4 10  1  0  0  0  0
 10 11  1  0  0  0  0
 12  7  1  1  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 16 18  1  0  0  0  0
 19 16  1  6  0  0  0
 12 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  1  0  0  0
 20 22  1  0  0  0  0
  6 22  1  0  0  0  0
 22 23  1  6  0  0  0
 23 24  1  0  0  0  0
 12 24  1  0  0  0  0
 24 25  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0189968

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)C1=CC2=C(C(O)=C1O)[C@@]13CCCC(C)(C)[C@@H]1[C@@H](O)[C@@H]2OC3=O

> <INCHI_IDENTIFIER>
InChI=1S/C20H26O5/c1-9(2)10-8-11-12(14(22)13(10)21)20-7-5-6-19(3,4)17(20)15(23)16(11)25-18(20)24/h8-9,15-17,21-23H,5-7H2,1-4H3/t15-,16+,17-,20-/m0/s1

> <INCHI_KEY>
UXVPWKDITRJELA-CLWJZODNSA-N

> <FORMULA>
C20H26O5

> <MOLECULAR_WEIGHT>
346.423

> <EXACT_MASS>
346.178023937

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
51

> <JCHEM_AVERAGE_POLARIZABILITY>
37.22489399149963

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1R,8R,9R,10S)-3,4,9-trihydroxy-11,11-dimethyl-5-(propan-2-yl)-16-oxatetracyclo[6.6.2.0^{1,10}.0^{2,7}]hexadeca-2(7),3,5-trien-15-one

> <JCHEM_LOGP>
3.5783442653333317

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.800377378219526

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.17673808522416

> <JCHEM_PKA_STRONGEST_BASIC>
-3.346079333490808

> <JCHEM_POLAR_SURFACE_AREA>
86.99000000000001

> <JCHEM_REFRACTIVITY>
92.71360000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(1R,8R,9R,10S)-3,4,9-trihydroxy-5-isopropyl-11,11-dimethyl-16-oxatetracyclo[6.6.2.0^{1,10}.0^{2,7}]hexadeca-2(7),3,5-trien-15-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 04-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   04-SEP-22         0                                  
HETATM    1  C   UNK     0      12.563  -0.572   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      11.958   0.910   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      13.078   2.048   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      10.358   1.241   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       9.895   2.710   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       8.392   3.044   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       7.351   1.909   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       7.813   0.440   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       6.548  -0.885   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       9.317   0.106   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      10.131  -1.330   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       5.551   1.600   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.386   0.414   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.827   0.124   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       2.133   1.529   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       2.909   2.893   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       1.379   3.519   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       2.905   4.504   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       4.534   2.891   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       5.628   4.107   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       5.358   5.740   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       7.213   4.068   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       6.553   2.626   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0       6.802   0.914   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       7.651  -0.714   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5   10                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7   22                                                  
CONECT    7    6    8   12                                                  
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8    4   11                                                  
CONECT   11   10                                                            
CONECT   12    7   13   19   24                                             
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17   18   19                                             
CONECT   17   16                                                            
CONECT   18   16                                                            
CONECT   19   16   12   20                                                  
CONECT   20   19   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20    6   23                                                  
CONECT   23   22   24                                                       
CONECT   24   23   12   25                                                  
CONECT   25   24                                                            
MASTER        0    0    0    0    0    0    0    0   25    0   56    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₀H₂₆O₅

Average Mass

346.4230 Da

Monoisotopic Mass

346.17802 Da

IUPAC Name

(1R,8R,9R,10S)-3,4,9-trihydroxy-11,11-dimethyl-5-(propan-2-yl)-16-oxatetracyclo[6.6.2.0^{1,10}.0^{2,7}]hexadeca-2(7),3,5-trien-15-one

Traditional Name

(1R,8R,9R,10S)-3,4,9-trihydroxy-5-isopropyl-11,11-dimethyl-16-oxatetracyclo[6.6.2.0^{1,10}.0^{2,7}]hexadeca-2(7),3,5-trien-15-one

CAS Registry Number

Not Available

SMILES

CC(C)C1=CC2=C(C(O)=C1O)[C@@]13CCCC(C)(C)[C@@H]1[C@@H](O)[C@@H]2OC3=O

InChI Identifier

InChI=1S/C20H26O5/c1-9(2)10-8-11-12(14(22)13(10)21)20-7-5-6-19(3,4)17(20)15(23)16(11)25-18(20)24/h8-9,15-17,21-23H,5-7H2,1-4H3/t15-,16+,17-,20-/m0/s1

InChI Key

UXVPWKDITRJELA-CLWJZODNSA-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 canariensis	LOTUS Database	35616633
Salvia columbariae	LOTUS Database	35616633
Salvia mellifera	LOTUS Database	35616633
Salvia munzii	LOTUS Database	35616633
Salvia officinalis	LOTUS Database	35616633
Salvia pachyphylla	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as diterpene lactones. These are diterpenoids containing a lactone moiety.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Terpene lactones

Direct Parent

Diterpene lactones

Alternative Parents

Substituents

Diterpene lactone
Diterpenoid
Phenanthrene
Benzopyran
Isochromane
Tetralin
2-benzopyran
Cumene
1-hydroxy-4-unsubstituted benzenoid
Phenol
Delta valerolactone
Delta_valerolactone
Benzenoid
Oxane
Secondary alcohol
Carboxylic acid ester
Lactone
Organoheterocyclic compound
Polyol
Carboxylic acid derivative
Oxacycle
Monocarboxylic acid or derivatives
Organic oxygen compound
Alcohol
Organooxygen compound
Organic oxide
Hydrocarbon derivative
Carbonyl group
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	3.58	ChemAxon
pKa (Strongest Acidic)	9.18	ChemAxon
pKa (Strongest Basic)	-3.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	86.99 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	92.71 m³·mol⁻¹	ChemAxon
Polarizability	37.22 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

C00037344

Chemspider ID

23339133

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

13820511

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Marrero JG, Moujir L, Andres LS, Montano NP, Araujo L, Luis JG: Semisynthesis and biological evaluation of abietane-type diterpenes. Revision of the structure of rosmaquinone. J Nat Prod. 2009 Aug;72(8):1385-9. doi: 10.1021/np900047p. [PubMed:19711987 ]
Zhang Y, Adelakun TA, Qu L, Li X, Li J, Han L, Wang T: New terpenoid glycosides obtained from Rosmarinus officinalis L. aerial parts. Fitoterapia. 2014 Dec;99:78-85. doi: 10.1016/j.fitote.2014.09.004. Epub 2014 Sep 6. [PubMed:25200369 ]
Li Z, Zhang X, Yang Z, Zhang Y, Xie Z: Biomimetic Synthesis of Isorosmanol and Przewalskin A. J Org Chem. 2018 Jan 5;83(1):437-442. doi: 10.1021/acs.joc.7b02369. Epub 2017 Dec 14. [PubMed:29191008 ]
Sun Y, Wang Y, Cai R, Zhang H, Wang Y: [Identification of the chemical compositionsof Verbena officinalis L. extract by high performance liquid chromatography-photodiode array-high resolution mass spectrometry]. Se Pu. 2017 Sep 8;35(9):987-994. doi: 10.3724/SP.J.1123.2017.05010. [PubMed:29048857 ]
Sallam A, Mira A, Ashour A, Shimizu K: Acetylcholine esterase inhibitors and melanin synthesis inhibitors from Salvia officinalis. Phytomedicine. 2016 Sep 15;23(10):1005-11. doi: 10.1016/j.phymed.2016.06.014. Epub 2016 Jun 21. [PubMed:27444345 ]
LOTUS database [Link]

Showing NP-Card for (1r,8r,9r,10s)-3,4,9-trihydroxy-5-isopropyl-11,11-dimethyl-16-oxatetracyclo[6.6.2.0¹,¹⁰.0²,⁷]hexadeca-2(7),3,5-trien-15-one (NP0189968)

MOL for NP0189968 ((1r,8r,9r,10s)-3,4,9-trihydroxy-5-isopropyl-11,11-dimethyl-16-oxatetracyclo[6.6.2.0¹,¹⁰.0²,⁷]hexadeca-2(7),3,5-trien-15-one)

3D MOL for NP0189968 ((1r,8r,9r,10s)-3,4,9-trihydroxy-5-isopropyl-11,11-dimethyl-16-oxatetracyclo[6.6.2.0¹,¹⁰.0²,⁷]hexadeca-2(7),3,5-trien-15-one)

3D SDF for NP0189968 ((1r,8r,9r,10s)-3,4,9-trihydroxy-5-isopropyl-11,11-dimethyl-16-oxatetracyclo[6.6.2.0¹,¹⁰.0²,⁷]hexadeca-2(7),3,5-trien-15-one)

3D-SDF for NP0189968 ((1r,8r,9r,10s)-3,4,9-trihydroxy-5-isopropyl-11,11-dimethyl-16-oxatetracyclo[6.6.2.0¹,¹⁰.0²,⁷]hexadeca-2(7),3,5-trien-15-one)

PDB for NP0189968 ((1r,8r,9r,10s)-3,4,9-trihydroxy-5-isopropyl-11,11-dimethyl-16-oxatetracyclo[6.6.2.0¹,¹⁰.0²,⁷]hexadeca-2(7),3,5-trien-15-one)

3D PDB for NP0189968 ((1r,8r,9r,10s)-3,4,9-trihydroxy-5-isopropyl-11,11-dimethyl-16-oxatetracyclo[6.6.2.0¹,¹⁰.0²,⁷]hexadeca-2(7),3,5-trien-15-one)

SMILES for NP0189968 ((1r,8r,9r,10s)-3,4,9-trihydroxy-5-isopropyl-11,11-dimethyl-16-oxatetracyclo[6.6.2.0¹,¹⁰.0²,⁷]hexadeca-2(7),3,5-trien-15-one)

INCHI for NP0189968 ((1r,8r,9r,10s)-3,4,9-trihydroxy-5-isopropyl-11,11-dimethyl-16-oxatetracyclo[6.6.2.0¹,¹⁰.0²,⁷]hexadeca-2(7),3,5-trien-15-one)

Structure for NP0189968 ((1r,8r,9r,10s)-3,4,9-trihydroxy-5-isopropyl-11,11-dimethyl-16-oxatetracyclo[6.6.2.0¹,¹⁰.0²,⁷]hexadeca-2(7),3,5-trien-15-one)

3D Structure for NP0189968 ((1r,8r,9r,10s)-3,4,9-trihydroxy-5-isopropyl-11,11-dimethyl-16-oxatetracyclo[6.6.2.0¹,¹⁰.0²,⁷]hexadeca-2(7),3,5-trien-15-one)