NP-MRD: Showing NP-Card for Isorosmanol (NP0048567)

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Record Information

Version

2.0

Created at

2022-03-17 20:58:29 UTC

Updated at

2022-03-17 20:58:29 UTC

NP-MRD ID

NP0048567

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Isorosmanol

Description

Isorosmanol belongs to the class of organic compounds known as diterpene lactones. These are diterpenoids containing a lactone moiety. Isorosmanol is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, isorosmanol has been detected, but not quantified in, a few different foods, such as common sages, herbs and spices, and rosemaries. Isorosmanol is found in Hypis dilatata, Plectranthus barbatus, Salvia canariensis, Salvia columbariae, Salvia mellifera and Salvia pachyphylla. Isorosmanol was first documented in 2009 (PMID: 19678545). This could make isorosmanol a potential biomarker for the consumption of these foods.

Structure

MOL SDF PDB SMILES InChI


  Mrv0541 02241211072D          

 25 28  0  0  0  0            999 V2000
   -2.4992   -0.2023    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4992   -1.0282    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7847   -1.4412    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0716   -1.0282    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0716   -0.2023    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7847    0.2092    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3572   -1.4412    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3558   -1.0282    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3558   -0.2023    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3572    0.2092    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0675    0.2092    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0675    1.0311    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3558    1.4412    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3572    1.0311    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0716    0.6236    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3572   -0.6152    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6553    1.2072    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0716    1.4412    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3558    2.2672    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7833    1.4412    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4992    1.0311    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7833    2.2672    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1977   -2.1570    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3718   -2.1570    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3572   -2.2672    0.0000 O   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 23  1  0  0  0  0
  3 24  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 15  1  0  0  0  0
  7  8  1  0  0  0  0
  7 25  1  0  0  0  0
  8  9  1  0  0  0  0
  8 16  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 20  1  0  0  0  0
 13 14  2  0  0  0  0
 13 19  1  0  0  0  0
 14 18  1  0  0  0  0
 15 16  1  0  0  0  0
 15 17  2  0  0  0  0
 20 21  1  0  0  0  0
 20 22  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0048567

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)C1=CC2=C(C(O)=C1O)C13CCCC(C)(C)C1C(O)C2OC3=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

> <INCHI_KEY>
UXVPWKDITRJELA-UHFFFAOYSA-N

> <FORMULA>
C20H26O5

> <MOLECULAR_WEIGHT>
346.4174

> <EXACT_MASS>
346.178023942

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
36.70515924772026

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
3,4,9-trihydroxy-11,11-dimethyl-5-(propan-2-yl)-16-oxatetracyclo[6.6.2.0¹,¹⁰.0²,⁷]hexadeca-2(7),3,5-trien-15-one

> <ALOGPS_LOGP>
3.23

> <JCHEM_LOGP>
3.5783442653333317

> <ALOGPS_LOGS>
-2.65

> <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>
92.7136

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
7.74e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
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

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  C   UNK     0      -4.665  -0.378   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -4.665  -1.919   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -3.331  -2.690   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -2.000  -1.919   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -2.000  -0.378   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -3.331   0.391   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -0.667  -2.690   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.664  -1.919   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.664  -0.378   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -0.667   0.391   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.993   0.391   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.993   1.925   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       0.664   2.690   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -0.667   1.925   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -2.000   1.164   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      -0.667  -1.148   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0      -3.090   2.253   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0      -2.000   2.690   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0       0.664   4.232   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       3.329   2.690   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       4.665   1.925   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       3.329   4.232   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -4.102  -4.026   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      -2.561  -4.026   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0      -0.667  -4.232   0.000  0.00  0.00           O+0
CONECT    1    2    6                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4   23   24                                             
CONECT    4    3    5    7                                                  
CONECT    5    4    6   10   15                                             
CONECT    6    1    5                                                       
CONECT    7    4    8   25                                                  
CONECT    8    7    9   16                                                  
CONECT    9    8   10   11                                                  
CONECT   10    5    9   14                                                  
CONECT   11    9   12                                                       
CONECT   12   11   13   20                                                  
CONECT   13   12   14   19                                                  
CONECT   14   10   13   18                                                  
CONECT   15    5   16   17                                                  
CONECT   16    8   15                                                       
CONECT   17   15                                                            
CONECT   18   14                                                            
CONECT   19   13                                                            
CONECT   20   12   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20                                                            
CONECT   23    3                                                            
CONECT   24    3                                                            
CONECT   25    7                                                            
MASTER        0    0    0    0    0    0    0    0   25    0   56    0
END

View in JSmol

Synonyms

Value	Source
6,11,12-Trihydroxy-8,11,13-abietatrien-20,7-olide	HMDB

Chemical Formula

C₂₀H₂₆O₅

Average Mass

346.4174 Da

Monoisotopic Mass

346.17802 Da

IUPAC Name

3,4,9-trihydroxy-11,11-dimethyl-5-(propan-2-yl)-16-oxatetracyclo[6.6.2.0¹,¹⁰.0²,⁷]hexadeca-2(7),3,5-trien-15-one

Traditional Name

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

CAS Registry Number

93780-80-4

SMILES

CC(C)C1=CC2=C(C(O)=C1O)C13CCCC(C)(C)C1C(O)C2OC3=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

InChI Key

UXVPWKDITRJELA-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Hypis dilatata	-	KNApSAcK
Plectranthus barbatus	LOTUS Database	35616633
Salvia canariensis	LOTUS Database	35616633
Salvia columbariae	LOTUS Database	35616633
Salvia mellifera	LOTUS Database	35616633
Salvia officinalis	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Salvia pachyphylla	Plant	KNApSAcK
Salvia rosmarinus	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases

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	3.23	ALOGPS
logP	3.58	ChemAxon
logS	-2.6	ALOGPS
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	36.71 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

HMDB0036661

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB015588

KNApSAcK ID

C00037344

Chemspider ID

10169083

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

11996616

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Park SY: Neuroprotective and neurotrophic effects of isorosmanol. Z Naturforsch C J Biosci. 2009 May-Jun;64(5-6):395-8. doi: 10.1515/znc-2009-5-616. [PubMed:19678545 ]

Showing NP-Card for Isorosmanol (NP0048567)

MOL for NP0048567 (Isorosmanol)

3D MOL for NP0048567 (Isorosmanol)

3D SDF for NP0048567 (Isorosmanol)

3D-SDF for NP0048567 (Isorosmanol)

PDB for NP0048567 (Isorosmanol)

3D PDB for NP0048567 (Isorosmanol)

SMILES for NP0048567 (Isorosmanol)

INCHI for NP0048567 (Isorosmanol)

Structure for NP0048567 (Isorosmanol)

3D Structure for NP0048567 (Isorosmanol)