NP-MRD: Showing NP-Card for 3,4-dihydroxy-5-isopropyl-8,9-dimethoxy-11,11-dimethyl-16-oxatetracyclo[7.5.2.0¹,¹⁰.0²,⁷]hexadeca-2,4,6-trien-15-one (NP0222409)

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Record Information

Version

2.0

Created at

2022-09-06 00:14:23 UTC

Updated at

2022-09-06 00:14:23 UTC

NP-MRD ID

NP0222409

Secondary Accession Numbers

None

Natural Product Identification

Common Name

3,4-dihydroxy-5-isopropyl-8,9-dimethoxy-11,11-dimethyl-16-oxatetracyclo[7.5.2.0¹,¹⁰.0²,⁷]hexadeca-2,4,6-trien-15-one

Description

6,7-Dimethoxy-7-epirosmanol belongs to the class of organic compounds known as diterpene lactones. These are diterpenoids containing a lactone moiety. 6,7-Dimethoxy-7-epirosmanol is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, 6,7-dimethoxy-7-epirosmanol has been detected, but not quantified in, herbs and spices and tea. 3,4-dihydroxy-5-isopropyl-8,9-dimethoxy-11,11-dimethyl-16-oxatetracyclo[7.5.2.0¹,¹⁰.0²,⁷]hexadeca-2,4,6-trien-15-one is found in Salvia officinalis. This could make 6,7-dimethoxy-7-epirosmanol a potential biomarker for the consumption of these foods.

Structure

MOL SDF PDB SMILES InChI


  Mrv0541 05061305322D          

 28 31  0  0  0  0            999 V2000
   -2.4323    0.0027    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4323   -0.8229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7181   -1.2358    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0052   -0.8229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0052    0.0027    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7181    0.4142    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2910   -1.2358    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4217   -0.8229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4217    0.0027    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2910    0.4142    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1333    0.4142    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1333    1.2358    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4217    1.6458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2910    1.2358    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8488    1.6486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8488    2.4743    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5632    1.2360    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4217    2.4715    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0052    1.6486    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3016   -1.8192    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5048   -2.0339    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0052    0.8284    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5672    1.4960    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3446   -0.1349    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2910   -2.0614    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1373   -1.2358    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0066   -2.4743    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8530   -0.8229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  6  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  3 20  1  0  0  0  0
  3 21  1  0  0  0  0
  4  5  1  0  0  0  0
  4  7  1  0  0  0  0
  5  6  1  0  0  0  0
  5 10  1  0  0  0  0
  5 22  1  0  0  0  0
  7  8  1  0  0  0  0
  7 24  1  0  0  0  0
  7 25  1  0  0  0  0
  8  9  1  0  0  0  0
  8 26  1  0  0  0  0
  9 10  2  0  0  0  0
  9 11  1  0  0  0  0
 10 14  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 12 15  1  0  0  0  0
 13 14  2  0  0  0  0
 13 18  1  0  0  0  0
 14 19  1  0  0  0  0
 15 16  1  0  0  0  0
 15 17  1  0  0  0  0
 22 23  2  0  0  0  0
 22 24  1  0  0  0  0
 25 27  1  0  0  0  0
 26 28  1  0  0  0  0
M  END


  Mrv0541 05061305322D          

 28 31  0  0  0  0            999 V2000
   -2.4323    0.0027    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4323   -0.8229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7181   -1.2358    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0052   -0.8229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0052    0.0027    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7181    0.4142    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2910   -1.2358    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4217   -0.8229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4217    0.0027    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2910    0.4142    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1333    0.4142    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1333    1.2358    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4217    1.6458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2910    1.2358    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8488    1.6486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8488    2.4743    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5632    1.2360    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4217    2.4715    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0052    1.6486    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3016   -1.8192    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5048   -2.0339    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0052    0.8284    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5672    1.4960    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3446   -0.1349    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2910   -2.0614    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1373   -1.2358    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0066   -2.4743    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8530   -0.8229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  6  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  3 20  1  0  0  0  0
  3 21  1  0  0  0  0
  4  5  1  0  0  0  0
  4  7  1  0  0  0  0
  5  6  1  0  0  0  0
  5 10  1  0  0  0  0
  5 22  1  0  0  0  0
  7  8  1  0  0  0  0
  7 24  1  0  0  0  0
  7 25  1  0  0  0  0
  8  9  1  0  0  0  0
  8 26  1  0  0  0  0
  9 10  2  0  0  0  0
  9 11  1  0  0  0  0
 10 14  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 12 15  1  0  0  0  0
 13 14  2  0  0  0  0
 13 18  1  0  0  0  0
 14 19  1  0  0  0  0
 15 16  1  0  0  0  0
 15 17  1  0  0  0  0
 22 23  2  0  0  0  0
 22 24  1  0  0  0  0
 25 27  1  0  0  0  0
 26 28  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0222409

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1C2=C(C(O)=C(O)C(=C2)C(C)C)C23CCCC(C)(C)C2C1(OC)OC3=O

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

> <INCHI_KEY>
MCHRWEBHSKWYBW-UHFFFAOYSA-N

> <FORMULA>
C22H30O6

> <MOLECULAR_WEIGHT>
390.47

> <EXACT_MASS>
390.204238692

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_AVERAGE_POLARIZABILITY>
41.48335580097524

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
3,4-dihydroxy-8,9-dimethoxy-11,11-dimethyl-5-(propan-2-yl)-16-oxatetracyclo[7.5.2.0¹,¹⁰.0²,⁷]hexadeca-2(7),3,5-trien-15-one

> <ALOGPS_LOGP>
3.96

> <JCHEM_LOGP>
4.5605624979999995

> <ALOGPS_LOGS>
-3.88

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.845564469742666

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.16954496212373

> <JCHEM_PKA_STRONGEST_BASIC>
-3.956939116759281

> <JCHEM_POLAR_SURFACE_AREA>
85.22000000000001

> <JCHEM_REFRACTIVITY>
103.73849999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.10e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3,4-dihydroxy-5-isopropyl-8,9-dimethoxy-11,11-dimethyl-16-oxatetracyclo[7.5.2.0¹,¹⁰.0²,⁷]hexadeca-2(7),3,5-trien-15-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 06-MAY-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAY-13         0                                  
HETATM    1  C   UNK     0      -4.540   0.005   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -4.540  -1.536   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -3.207  -2.307   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -1.876  -1.536   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -1.876   0.005   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -3.207   0.773   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -0.543  -2.307   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.787  -1.536   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.787   0.005   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -0.543   0.773   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.115   0.773   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.115   2.307   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       0.787   3.072   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -0.543   2.307   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       3.451   3.077   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       3.451   4.619   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       4.785   2.307   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       0.787   4.613   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0      -1.876   3.077   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0      -4.296  -3.396   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -2.809  -3.797   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -1.876   1.546   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0      -2.925   2.793   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0      -0.643  -0.252   0.000  0.00  0.00           O+0
HETATM   25  O   UNK     0      -0.543  -3.848   0.000  0.00  0.00           O+0
HETATM   26  O   UNK     0       2.123  -2.307   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0      -1.879  -4.619   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       3.459  -1.536   0.000  0.00  0.00           C+0
CONECT    1    2    6                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4   20   21                                             
CONECT    4    3    5    7                                                  
CONECT    5    4    6   10   22                                             
CONECT    6    1    5                                                       
CONECT    7    4    8   24   25                                             
CONECT    8    7    9   26                                                  
CONECT    9    8   10   11                                                  
CONECT   10    5    9   14                                                  
CONECT   11    9   12                                                       
CONECT   12   11   13   15                                                  
CONECT   13   12   14   18                                                  
CONECT   14   10   13   19                                                  
CONECT   15   12   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15                                                            
CONECT   18   13                                                            
CONECT   19   14                                                            
CONECT   20    3                                                            
CONECT   21    3                                                            
CONECT   22    5   23   24                                                  
CONECT   23   22                                                            
CONECT   24    7   22                                                       
CONECT   25    7   27                                                       
CONECT   26    8   28                                                       
CONECT   27   25                                                            
CONECT   28   26                                                            
MASTER        0    0    0    0    0    0    0    0   28    0   62    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₂H₃₀O₆

Average Mass

390.4700 Da

Monoisotopic Mass

390.20424 Da

IUPAC Name

3,4-dihydroxy-8,9-dimethoxy-11,11-dimethyl-5-(propan-2-yl)-16-oxatetracyclo[7.5.2.0¹,¹⁰.0²,⁷]hexadeca-2(7),3,5-trien-15-one

Traditional Name

3,4-dihydroxy-5-isopropyl-8,9-dimethoxy-11,11-dimethyl-16-oxatetracyclo[7.5.2.0¹,¹⁰.0²,⁷]hexadeca-2(7),3,5-trien-15-one

CAS Registry Number

Not Available

SMILES

COC1C2=C(C(O)=C(O)C(=C2)C(C)C)C23CCCC(C)(C)C2C1(OC)OC3=O

InChI Identifier

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

InChI Key

MCHRWEBHSKWYBW-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Salvia officinalis	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

Not Available

Substituents

Not Available

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	3.96	ALOGPS
logP	4.56	ChemAxon
logS	-3.9	ALOGPS
pKa (Strongest Acidic)	9.17	ChemAxon
pKa (Strongest Basic)	-4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	85.22 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	103.74 m³·mol⁻¹	ChemAxon
Polarizability	41.48 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

HMDB0030844

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB002803

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

131751086

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 3,4-dihydroxy-5-isopropyl-8,9-dimethoxy-11,11-dimethyl-16-oxatetracyclo[7.5.2.0¹,¹⁰.0²,⁷]hexadeca-2,4,6-trien-15-one (NP0222409)

MOL for NP0222409 (3,4-dihydroxy-5-isopropyl-8,9-dimethoxy-11,11-dimethyl-16-oxatetracyclo[7.5.2.0¹,¹⁰.0²,⁷]hexadeca-2,4,6-trien-15-one)

3D MOL for NP0222409 (3,4-dihydroxy-5-isopropyl-8,9-dimethoxy-11,11-dimethyl-16-oxatetracyclo[7.5.2.0¹,¹⁰.0²,⁷]hexadeca-2,4,6-trien-15-one)

3D SDF for NP0222409 (3,4-dihydroxy-5-isopropyl-8,9-dimethoxy-11,11-dimethyl-16-oxatetracyclo[7.5.2.0¹,¹⁰.0²,⁷]hexadeca-2,4,6-trien-15-one)

3D-SDF for NP0222409 (3,4-dihydroxy-5-isopropyl-8,9-dimethoxy-11,11-dimethyl-16-oxatetracyclo[7.5.2.0¹,¹⁰.0²,⁷]hexadeca-2,4,6-trien-15-one)

PDB for NP0222409 (3,4-dihydroxy-5-isopropyl-8,9-dimethoxy-11,11-dimethyl-16-oxatetracyclo[7.5.2.0¹,¹⁰.0²,⁷]hexadeca-2,4,6-trien-15-one)

3D PDB for NP0222409 (3,4-dihydroxy-5-isopropyl-8,9-dimethoxy-11,11-dimethyl-16-oxatetracyclo[7.5.2.0¹,¹⁰.0²,⁷]hexadeca-2,4,6-trien-15-one)

SMILES for NP0222409 (3,4-dihydroxy-5-isopropyl-8,9-dimethoxy-11,11-dimethyl-16-oxatetracyclo[7.5.2.0¹,¹⁰.0²,⁷]hexadeca-2,4,6-trien-15-one)

INCHI for NP0222409 (3,4-dihydroxy-5-isopropyl-8,9-dimethoxy-11,11-dimethyl-16-oxatetracyclo[7.5.2.0¹,¹⁰.0²,⁷]hexadeca-2,4,6-trien-15-one)

Structure for NP0222409 (3,4-dihydroxy-5-isopropyl-8,9-dimethoxy-11,11-dimethyl-16-oxatetracyclo[7.5.2.0¹,¹⁰.0²,⁷]hexadeca-2,4,6-trien-15-one)

3D Structure for NP0222409 (3,4-dihydroxy-5-isopropyl-8,9-dimethoxy-11,11-dimethyl-16-oxatetracyclo[7.5.2.0¹,¹⁰.0²,⁷]hexadeca-2,4,6-trien-15-one)