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Showing NP-Card for (1r,8s,9s,10s)-3,4-dihydroxy-5-isopropyl-6,8-dimethoxy-11,11-dimethyl-16-oxatetracyclo[7.5.2.0¹,¹⁰.0²,⁷]hexadeca-2(7),3,5-trien-15-one (NP0249063)

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Record Information
Version2.0
Created at2022-09-07 11:31:16 UTC
Updated at2022-09-07 11:31:16 UTC
NP-MRD IDNP0249063
Secondary Accession NumbersNone
Natural Product Identification
Common Name(1r,8s,9s,10s)-3,4-dihydroxy-5-isopropyl-6,8-dimethoxy-11,11-dimethyl-16-oxatetracyclo[7.5.2.0¹,¹⁰.0²,⁷]hexadeca-2(7),3,5-trien-15-one
Description7,14-Dimethoxyrosmanol belongs to the class of organic compounds known as diterpene lactones. These are diterpenoids containing a lactone moiety. Based on a literature review very few articles have been published on 7,14-Dimethoxyrosmanol.
Structure
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MOLSDFPDBSMILESInChI

MOL for NP0249063 ((1r,8s,9s,10s)-3,4-dihydroxy-5-isopropyl-6,8-dimethoxy-11,11-dimethyl-16-oxatetracyclo[7.5.2.0¹,¹⁰.0²,⁷]hexadeca-2(7),3,5-trien-15-one)


  Mrv1652309072213312D          

 28 31  0  0  1  0            999 V2000
    4.3683    3.0844    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5451    3.0289    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1815    2.2884    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6411    1.6032    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4642    1.6586    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8278    2.3992    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9238    0.9735    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2775    0.8627    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7371    0.1775    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4544    0.8072    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0908    0.0667    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9948    1.4924    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3584    2.2330    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0061    2.9789    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.5253    3.6200    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2298    4.3903    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2032    3.1686    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.5543    2.6591    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5481    1.8342    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1979    1.4818    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1892    1.3149    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.5917    0.7459    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1997    0.9788    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3937    1.7807    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2037    2.3497    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4604    2.8392    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5705    3.0886    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9951    2.1168    0.0000 C   0  0  2  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  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  5  7  1  0  0  0  0
  4  8  1  0  0  0  0
  8  9  1  0  0  0  0
  8 10  2  0  0  0  0
 10 11  1  0  0  0  0
 10 12  1  0  0  0  0
 12 13  2  0  0  0  0
  3 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  1  0  0  0
 15 16  1  0  0  0  0
 14 17  1  0  0  0  0
 17 18  1  6  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 21 19  1  6  0  0  0
 12 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 25 27  1  0  0  0  0
 25 28  1  0  0  0  0
 28 17  1  6  0  0  0
 21 28  1  0  0  0  0
M  END
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3D MOL for NP0249063 ((1r,8s,9s,10s)-3,4-dihydroxy-5-isopropyl-6,8-dimethoxy-11,11-dimethyl-16-oxatetracyclo[7.5.2.0¹,¹⁰.0²,⁷]hexadeca-2(7),3,5-trien-15-one)

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3D SDF for NP0249063 ((1r,8s,9s,10s)-3,4-dihydroxy-5-isopropyl-6,8-dimethoxy-11,11-dimethyl-16-oxatetracyclo[7.5.2.0¹,¹⁰.0²,⁷]hexadeca-2(7),3,5-trien-15-one)

  Mrv1652309072213312D          

 28 31  0  0  1  0            999 V2000
    4.3683    3.0844    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5451    3.0289    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1815    2.2884    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6411    1.6032    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4642    1.6586    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8278    2.3992    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9238    0.9735    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2775    0.8627    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7371    0.1775    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4544    0.8072    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0908    0.0667    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9948    1.4924    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3584    2.2330    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0061    2.9789    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.5253    3.6200    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2298    4.3903    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2032    3.1686    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.5543    2.6591    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5481    1.8342    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1979    1.4818    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1892    1.3149    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.5917    0.7459    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1997    0.9788    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3937    1.7807    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2037    2.3497    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4604    2.8392    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5705    3.0886    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9951    2.1168    0.0000 C   0  0  2  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  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  5  7  1  0  0  0  0
  4  8  1  0  0  0  0
  8  9  1  0  0  0  0
  8 10  2  0  0  0  0
 10 11  1  0  0  0  0
 10 12  1  0  0  0  0
 12 13  2  0  0  0  0
  3 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  1  0  0  0
 15 16  1  0  0  0  0
 14 17  1  0  0  0  0
 17 18  1  6  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 21 19  1  6  0  0  0
 12 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 25 27  1  0  0  0  0
 25 28  1  0  0  0  0
 28 17  1  6  0  0  0
 21 28  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0249063

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CO[C@@H]1[C@H]2OC(=O)[C@@]3(CCCC(C)(C)[C@H]23)C2=C1C(OC)=C(C(C)C)C(O)=C2O

> <INCHI_IDENTIFIER>
InChI=1S/C22H30O6/c1-10(2)11-14(23)15(24)13-12(16(11)26-5)17(27-6)18-19-21(3,4)8-7-9-22(13,19)20(25)28-18/h10,17-19,23-24H,7-9H2,1-6H3/t17-,18+,19-,22-/m0/s1

> <INCHI_KEY>
DHNUPRDARUHAJK-WEMPKCCASA-N

> <FORMULA>
C22H30O6

> <MOLECULAR_WEIGHT>
390.476

> <EXACT_MASS>
390.204238686

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
58

> <JCHEM_AVERAGE_POLARIZABILITY>
41.92680254069453

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1R,8S,9S,10S)-3,4-dihydroxy-6,8-dimethoxy-11,11-dimethyl-5-(propan-2-yl)-16-oxatetracyclo[7.5.2.0^{1,10}.0^{2,7}]hexadeca-2(7),3,5-trien-15-one

> <JCHEM_LOGP>
4.063799503333332

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.872419694432121

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.505291545311529

> <JCHEM_PKA_STRONGEST_BASIC>
-4.088985859188126

> <JCHEM_POLAR_SURFACE_AREA>
85.22

> <JCHEM_REFRACTIVITY>
103.928

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(1R,8S,9S,10S)-3,4-dihydroxy-5-isopropyl-6,8-dimethoxy-11,11-dimethyl-16-oxatetracyclo[7.5.2.0^{1,10}.0^{2,7}]hexadeca-2(7),3,5-trien-15-one

> <JCHEM_VEBER_RULE>
0

$$$$

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3D-SDF for NP0249063 ((1r,8s,9s,10s)-3,4-dihydroxy-5-isopropyl-6,8-dimethoxy-11,11-dimethyl-16-oxatetracyclo[7.5.2.0¹,¹⁰.0²,⁷]hexadeca-2(7),3,5-trien-15-one)
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PDB for NP0249063 ((1r,8s,9s,10s)-3,4-dihydroxy-5-isopropyl-6,8-dimethoxy-11,11-dimethyl-16-oxatetracyclo[7.5.2.0¹,¹⁰.0²,⁷]hexadeca-2(7),3,5-trien-15-one)
HEADER    PROTEIN                                 07-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   07-SEP-22         0                                  
HETATM    1  C   UNK     0       8.154   5.757   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       6.618   5.654   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       5.939   4.272   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       6.797   2.993   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       8.333   3.096   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       9.012   4.479   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       9.191   1.817   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       6.118   1.610   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       6.976   0.331   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       4.582   1.507   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       3.903   0.124   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       3.724   2.786   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.402   4.168   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       3.745   5.561   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       4.714   6.757   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       4.162   8.195   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       2.246   5.915   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       1.035   4.964   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       1.023   3.424   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0      -0.369   2.766   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       2.220   2.454   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       1.105   1.392   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -0.373   1.827   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      -0.735   3.324   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       0.380   4.386   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      -0.859   5.300   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       1.065   5.765   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       1.858   3.951   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   13                                                  
CONECT    4    3    5    8                                                  
CONECT    5    4    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5                                                            
CONECT    8    4    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10   13   21                                                  
CONECT   13   12    3   14                                                  
CONECT   14   13   15   17                                                  
CONECT   15   14   16                                                       
CONECT   16   15                                                            
CONECT   17   14   18   28                                                  
CONECT   18   17   19                                                       
CONECT   19   18   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19   12   22   28                                             
CONECT   22   21   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24   26   27   28                                             
CONECT   26   25                                                            
CONECT   27   25                                                            
CONECT   28   25   17   21                                                  
MASTER        0    0    0    0    0    0    0    0   28    0   62    0
END

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3D PDB for NP0249063 ((1r,8s,9s,10s)-3,4-dihydroxy-5-isopropyl-6,8-dimethoxy-11,11-dimethyl-16-oxatetracyclo[7.5.2.0¹,¹⁰.0²,⁷]hexadeca-2(7),3,5-trien-15-one)
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SMILES for NP0249063 ((1r,8s,9s,10s)-3,4-dihydroxy-5-isopropyl-6,8-dimethoxy-11,11-dimethyl-16-oxatetracyclo[7.5.2.0¹,¹⁰.0²,⁷]hexadeca-2(7),3,5-trien-15-one)
CO[C@@H]1[C@H]2OC(=O)[C@@]3(CCCC(C)(C)[C@H]23)C2=C1C(OC)=C(C(C)C)C(O)=C2O
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INCHI for NP0249063 ((1r,8s,9s,10s)-3,4-dihydroxy-5-isopropyl-6,8-dimethoxy-11,11-dimethyl-16-oxatetracyclo[7.5.2.0¹,¹⁰.0²,⁷]hexadeca-2(7),3,5-trien-15-one)
InChI=1S/C22H30O6/c1-10(2)11-14(23)15(24)13-12(16(11)26-5)17(27-6)18-19-21(3,4)8-7-9-22(13,19)20(25)28-18/h10,17-19,23-24H,7-9H2,1-6H3/t17-,18+,19-,22-/m0/s1
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SynonymsNot Available
Chemical FormulaC22H30O6
Average Mass390.4760 Da
Monoisotopic Mass390.20424 Da
IUPAC Name(1R,8S,9S,10S)-3,4-dihydroxy-6,8-dimethoxy-11,11-dimethyl-5-(propan-2-yl)-16-oxatetracyclo[7.5.2.0^{1,10}.0^{2,7}]hexadeca-2(7),3,5-trien-15-one
Traditional Name(1R,8S,9S,10S)-3,4-dihydroxy-5-isopropyl-6,8-dimethoxy-11,11-dimethyl-16-oxatetracyclo[7.5.2.0^{1,10}.0^{2,7}]hexadeca-2(7),3,5-trien-15-one
CAS Registry NumberNot Available
SMILES
CO[C@@H]1[C@H]2OC(=O)[C@@]3(CCCC(C)(C)[C@H]23)C2=C1C(OC)=C(C(C)C)C(O)=C2O
InChI Identifier
InChI=1S/C22H30O6/c1-10(2)11-14(23)15(24)13-12(16(11)26-5)17(27-6)18-19-21(3,4)8-7-9-22(13,19)20(25)28-18/h10,17-19,23-24H,7-9H2,1-6H3/t17-,18+,19-,22-/m0/s1
InChI KeyDHNUPRDARUHAJK-WEMPKCCASA-N
Experimental Spectra
Not Available
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of OriginNot Available
Chemical Taxonomy
Description Belongs to the class of organic compounds known as diterpene lactones. These are diterpenoids containing a lactone moiety.
KingdomOrganic compounds  
Super ClassLipids and lipid-like molecules  
ClassPrenol lipids  
Sub ClassTerpene lactones  
Direct ParentDiterpene lactones  
Alternative Parents
Substituents
  • Diterpene lactone
    • 

  • Diterpenoid
    • 

  • Phenanthrene
    • 

  • Benzoxepine
    • 

  • Tetralin
    • 

  • Cumene
    • 

  • Anisole
    • 

  • Phenol ether
    • 

  • Alkyl aryl ether
    • 

  • Phenol
    • 

  • Benzenoid
    • 

  • Gamma butyrolactone
    • 

  • Oxolane
    • 

  • Carboxylic acid ester
    • 

  • Lactone
    • 

  • Ether
    • 

  • Organoheterocyclic compound
    • 

  • Dialkyl ether
    • 

  • Oxacycle
    • 

  • Carboxylic acid derivative
    • 

  • Monocarboxylic acid or derivatives
    • 

  • Organooxygen compound
    • 

  • Organic oxygen compound
    • 

  • Carbonyl group
    • 

  • Hydrocarbon derivative
    • 

  • Organic oxide
    • 

  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP4.06ChemAxon
pKa (Strongest Acidic)9.51ChemAxon
pKa (Strongest Basic)-4.1ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area85.22 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity103.93 m³·mol⁻¹ChemAxon
Polarizability41.93 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID103885111  
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound95224642  
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. LOTUS database [Link]