NP-MRD: Showing NP-Card for (1r,8s,10s)-3,4-dihydroxy-5-(1-hydroxypropan-2-yl)-11,11-dimethyl-16-oxatetracyclo[6.6.2.0¹,¹⁰.0²,⁷]hexadeca-2(7),3,5-trien-15-one (NP0273772)

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Record Information

Version

2.0

Created at

2022-09-08 20:55:42 UTC

Updated at

2022-09-08 20:55:42 UTC

NP-MRD ID

NP0273772

Secondary Accession Numbers

None

Natural Product Identification

Common Name

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

Description

16-Hydroxycarnosol belongs to the class of organic compounds known as diterpene lactones. These are diterpenoids containing a lactone moiety. (1r,8s,10s)-3,4-dihydroxy-5-(1-hydroxypropan-2-yl)-11,11-dimethyl-16-oxatetracyclo[6.6.2.0¹,¹⁰.0²,⁷]hexadeca-2(7),3,5-trien-15-one is found in Salvia apiana, Salvia mellifera, Salvia munzii and Salvia rubescens. (1r,8s,10s)-3,4-dihydroxy-5-(1-hydroxypropan-2-yl)-11,11-dimethyl-16-oxatetracyclo[6.6.2.0¹,¹⁰.0²,⁷]hexadeca-2(7),3,5-trien-15-one was first documented in 2005 (PMID: 16327182). Based on a literature review a small amount of articles have been published on 16-hydroxycarnosol (PMID: 17190465) (PMID: 28025900).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309082222552D          

 25 28  0  0  1  0            999 V2000
    6.7510   -0.2935    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4226    0.4885    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9516    1.1380    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6583    1.9090    0.0000 O   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
    3.5178   -0.4467    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
    5.4033   -0.7331    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
    0.8093    1.9710    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4832    2.4412    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  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
    4.1260   -0.3485    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
  3  4  1  0  0  0  0
  2  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  9 11  2  0  0  0  0
  5 11  1  0  0  0  0
 11 12  1  0  0  0  0
 13  8  1  1  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
 17 18  1  0  0  0  0
 17 19  1  0  0  0  0
 17 20  1  0  0  0  0
 13 20  1  0  0  0  0
 20 21  1  6  0  0  0
 21 22  1  0  0  0  0
  7 22  1  0  0  0  0
 22 23  1  6  0  0  0
 23 24  1  0  0  0  0
 13 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
    4.6117   -1.7218    0.8848 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3609   -0.8811   -0.3550 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.1862    0.3962   -0.1137 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6984    0.9942    1.0688 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9423   -0.4367   -0.3828 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1603   -0.5975    0.7530 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8688   -0.1752    0.7410 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3067    0.4133   -0.3762 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0564    0.5827   -1.5077 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5128    1.1756   -2.6514 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3903    0.1435   -1.4877 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0919    0.3401   -2.6615 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1093    0.8125   -0.2094 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.7273    1.6274   -1.2471 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2180    1.7596   -0.9336 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7821    0.3523   -1.1122 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3019   -0.4280    0.0847 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7860   -1.8692   -0.1328 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9551    0.0574    1.3437 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8239   -0.4640    0.1449 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.3180   -1.0220    1.4522 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0585   -0.3049    1.9247 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.5035    1.0425    2.1621 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0771    1.6473    1.0530 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5273    2.8056    1.1230 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6635   -2.1118    0.7647 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6112   -1.0624    1.7691 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9292   -2.5631    0.9799 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6560   -1.3566   -1.2863 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2297    0.1228    0.0598 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1233    1.0906   -0.9536 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9176    1.5487    0.9166 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5568   -1.0528    1.6516 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0693    1.2979   -3.4799 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0331    0.0537   -2.7622 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2930    2.6294   -1.2706 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7206    1.2200   -2.2769 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4365    2.1525    0.0525 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6449    2.3804   -1.7632 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8850    0.4258   -1.1189 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3749   -0.0451   -2.0457 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5687   -2.5138    0.7199 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3243   -2.2090   -1.0762 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8879   -1.7745   -0.3440 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9435    0.4924    1.0881 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1563   -0.8248    2.0165 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3213    0.8104    1.8906 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4899   -1.2106   -0.6387 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0773   -0.8692    2.2705 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0477   -2.1044    1.3817 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3831   -0.7761    2.7791 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  2  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  1  0
  9 11  2  0
 11 12  1  0
  8 13  1  0
 13 14  1  6
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 17 19  1  0
 17 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  2  0
 11  5  1  0
 20 13  1  0
 22  7  1  0
 24 13  1  0
  1 26  1  0
  1 27  1  0
  1 28  1  0
  2 29  1  6
  3 30  1  0
  3 31  1  0
  4 32  1  0
  6 33  1  0
 10 34  1  0
 12 35  1  0
 14 36  1  0
 14 37  1  0
 15 38  1  0
 15 39  1  0
 16 40  1  0
 16 41  1  0
 18 42  1  0
 18 43  1  0
 18 44  1  0
 19 45  1  0
 19 46  1  0
 19 47  1  0
 20 48  1  6
 21 49  1  0
 21 50  1  0
 22 51  1  1
M  END


  Mrv1652309082222552D          

 25 28  0  0  1  0            999 V2000
    6.7510   -0.2935    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4226    0.4885    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9516    1.1380    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6583    1.9090    0.0000 O   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
    3.5178   -0.4467    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
    5.4033   -0.7331    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
    0.8093    1.9710    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4832    2.4412    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  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
    4.1260   -0.3485    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
  3  4  1  0  0  0  0
  2  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  9 11  2  0  0  0  0
  5 11  1  0  0  0  0
 11 12  1  0  0  0  0
 13  8  1  1  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
 17 18  1  0  0  0  0
 17 19  1  0  0  0  0
 17 20  1  0  0  0  0
 13 20  1  0  0  0  0
 20 21  1  6  0  0  0
 21 22  1  0  0  0  0
  7 22  1  0  0  0  0
 22 23  1  6  0  0  0
 23 24  1  0  0  0  0
 13 24  1  0  0  0  0
 24 25  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0273772

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C20H26O5/c1-10(9-21)11-7-12-13-8-14-19(2,3)5-4-6-20(14,18(24)25-13)15(12)17(23)16(11)22/h7,10,13-14,21-23H,4-6,8-9H2,1-3H3/t10?,13-,14-,20+/m0/s1

> <INCHI_KEY>
MWLHJCBZAWPKEY-NUDIBWDTSA-N

> <FORMULA>
C20H26O5

> <MOLECULAR_WEIGHT>
346.423

> <EXACT_MASS>
346.178023937

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
51

> <JCHEM_AVERAGE_POLARIZABILITY>
37.321070392521975

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <JCHEM_LOGP>
3.2165692556666667

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.730422423300816

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.119295817105517

> <JCHEM_PKA_STRONGEST_BASIC>
-2.67237343164975

> <JCHEM_POLAR_SURFACE_AREA>
86.99

> <JCHEM_REFRACTIVITY>
93.28079999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(1R,8S,10S)-3,4-dihydroxy-5-(1-hydroxypropan-2-yl)-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                                 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      12.602  -0.548   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      11.989   0.912   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      12.976   2.124   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0      12.429   3.564   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0      10.358   1.241   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       9.895   2.710   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       8.392   3.044   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       7.351   1.909   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       7.813   0.440   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       6.567  -0.834   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       9.317   0.106   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      10.086  -1.368   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       5.551   1.600   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.386   0.414   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       2.827   0.124   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       2.133   1.529   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       2.909   2.893   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       1.511   3.679   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       2.769   4.557   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       4.534   2.891   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       5.628   4.107   0.000  0.00  0.00           C+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       7.702  -0.651   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    5                                                  
CONECT    3    2    4                                                       
CONECT    4    3                                                            
CONECT    5    2    6   11                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8   22                                                  
CONECT    8    7    9   13                                                  
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9    5   12                                                  
CONECT   12   11                                                            
CONECT   13    8   14   20   24                                             
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18   19   20                                             
CONECT   18   17                                                            
CONECT   19   17                                                            
CONECT   20   17   13   21                                                  
CONECT   21   20   22                                                       
CONECT   22   21    7   23                                                  
CONECT   23   22   24                                                       
CONECT   24   23   13   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,8S,10S)-3,4-dihydroxy-5-(1-hydroxypropan-2-yl)-11,11-dimethyl-16-oxatetracyclo[6.6.2.0^{1,10}.0^{2,7}]hexadeca-2(7),3,5-trien-15-one

Traditional Name

(1R,8S,10S)-3,4-dihydroxy-5-(1-hydroxypropan-2-yl)-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(CO)C1=CC2=C(C(O)=C1O)[C@@]13CCCC(C)(C)[C@@H]1C[C@@H]2OC3=O

InChI Identifier

InChI=1S/C20H26O5/c1-10(9-21)11-7-12-13-8-14-19(2,3)5-4-6-20(14,18(24)25-13)15(12)17(23)16(11)22/h7,10,13-14,21-23H,4-6,8-9H2,1-3H3/t10?,13-,14-,20+/m0/s1

InChI Key

MWLHJCBZAWPKEY-NUDIBWDTSA-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 apiana	LOTUS Database	35616633
Salvia mellifera	LOTUS Database	35616633
Salvia munzii	LOTUS Database	35616633
Salvia rubescens	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
2-benzopyran
Tetralin
1-hydroxy-4-unsubstituted benzenoid
Delta valerolactone
Delta_valerolactone
Phenol
Benzenoid
Oxane
Carboxylic acid ester
Lactone
Organoheterocyclic compound
Oxacycle
Carboxylic acid derivative
Monocarboxylic acid or derivatives
Primary alcohol
Hydrocarbon derivative
Alcohol
Carbonyl group
Organic oxide
Organic oxygen compound
Organooxygen 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	3.22	ChemAxon
pKa (Strongest Acidic)	9.12	ChemAxon
pKa (Strongest Basic)	-2.7	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	2	ChemAxon
Refractivity	93.28 m³·mol⁻¹	ChemAxon
Polarizability	37.32 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

C00031517

Chemspider ID

23339135

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

44566424

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Guerrero IC, Andres LS, Leon LG, Machin RP, Padron JM, Luis JG, Delgadillo J: Abietane diterpenoids from Salvia pachyphylla and S. clevelandii with cytotoxic activity against human cancer cell lines. J Nat Prod. 2006 Dec;69(12):1803-5. doi: 10.1021/np060279i. [PubMed:17190465 ]
Srivedavyasasri R, Hayes T, Ross SA: Phytochemical and biological evaluation of Salvia apiana. Nat Prod Res. 2017 Sep;31(17):2058-2061. doi: 10.1080/14786419.2016.1269096. Epub 2016 Dec 27. [PubMed:28025900 ]
Marrero JG, Andres LS, Luis JG: Quinone derivatives by chemical transformations of 16-hydroxycarnosol from Salvia species. Chem Pharm Bull (Tokyo). 2005 Dec;53(12):1524-9. doi: 10.1248/cpb.53.1524. [PubMed:16327182 ]
LOTUS database [Link]

Showing NP-Card for (1r,8s,10s)-3,4-dihydroxy-5-(1-hydroxypropan-2-yl)-11,11-dimethyl-16-oxatetracyclo[6.6.2.0¹,¹⁰.0²,⁷]hexadeca-2(7),3,5-trien-15-one (NP0273772)

MOL for NP0273772 ((1r,8s,10s)-3,4-dihydroxy-5-(1-hydroxypropan-2-yl)-11,11-dimethyl-16-oxatetracyclo[6.6.2.0¹,¹⁰.0²,⁷]hexadeca-2(7),3,5-trien-15-one)

3D MOL for NP0273772 ((1r,8s,10s)-3,4-dihydroxy-5-(1-hydroxypropan-2-yl)-11,11-dimethyl-16-oxatetracyclo[6.6.2.0¹,¹⁰.0²,⁷]hexadeca-2(7),3,5-trien-15-one)

3D SDF for NP0273772 ((1r,8s,10s)-3,4-dihydroxy-5-(1-hydroxypropan-2-yl)-11,11-dimethyl-16-oxatetracyclo[6.6.2.0¹,¹⁰.0²,⁷]hexadeca-2(7),3,5-trien-15-one)

3D-SDF for NP0273772 ((1r,8s,10s)-3,4-dihydroxy-5-(1-hydroxypropan-2-yl)-11,11-dimethyl-16-oxatetracyclo[6.6.2.0¹,¹⁰.0²,⁷]hexadeca-2(7),3,5-trien-15-one)

PDB for NP0273772 ((1r,8s,10s)-3,4-dihydroxy-5-(1-hydroxypropan-2-yl)-11,11-dimethyl-16-oxatetracyclo[6.6.2.0¹,¹⁰.0²,⁷]hexadeca-2(7),3,5-trien-15-one)

3D PDB for NP0273772 ((1r,8s,10s)-3,4-dihydroxy-5-(1-hydroxypropan-2-yl)-11,11-dimethyl-16-oxatetracyclo[6.6.2.0¹,¹⁰.0²,⁷]hexadeca-2(7),3,5-trien-15-one)

SMILES for NP0273772 ((1r,8s,10s)-3,4-dihydroxy-5-(1-hydroxypropan-2-yl)-11,11-dimethyl-16-oxatetracyclo[6.6.2.0¹,¹⁰.0²,⁷]hexadeca-2(7),3,5-trien-15-one)

INCHI for NP0273772 ((1r,8s,10s)-3,4-dihydroxy-5-(1-hydroxypropan-2-yl)-11,11-dimethyl-16-oxatetracyclo[6.6.2.0¹,¹⁰.0²,⁷]hexadeca-2(7),3,5-trien-15-one)

Structure for NP0273772 ((1r,8s,10s)-3,4-dihydroxy-5-(1-hydroxypropan-2-yl)-11,11-dimethyl-16-oxatetracyclo[6.6.2.0¹,¹⁰.0²,⁷]hexadeca-2(7),3,5-trien-15-one)

3D Structure for NP0273772 ((1r,8s,10s)-3,4-dihydroxy-5-(1-hydroxypropan-2-yl)-11,11-dimethyl-16-oxatetracyclo[6.6.2.0¹,¹⁰.0²,⁷]hexadeca-2(7),3,5-trien-15-one)