NP-MRD: Showing NP-Card for Sesquiterpenes (NP0046552)

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Record Information

Version

2.0

Created at

2022-03-17 20:07:47 UTC

Updated at

2022-03-17 20:07:47 UTC

NP-MRD ID

NP0046552

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Sesquiterpenes

Description

Sesquiterpenes belongs to the class of organic compounds known as eudesmanolides, secoeudesmanolides, and derivatives. These are terpenoids with a structure based on the eudesmanolide (a 3,5a,9-trimethyl-naphtho[1,2-b]furan-2-one derivative) or secoeudesmanolide (a 3,6-dimethyl-5-(pentan-2-yl)-1-benzofuran-2-one derivative) skeleton. Sesquiterpenes is found in Artemisia annua , Artemisia caerulescens, Artemisia cina, Artemisia compacta, Artemisia finita, Artemisia schrenkiana, Artemisia spp. and Artemisia sublessingiana. Sesquiterpenes is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL SDF PDB SMILES InChI


  Mrv0541 02241220452D          

 18 20  0  0  1  0            999 V2000
    1.5452    0.1607    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1752   -0.3719    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.9765   -0.1753    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.3664    0.5517    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1910    0.5775    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6256   -0.1238    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.4502   -0.0980    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8849   -0.7992    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4949   -1.5262    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9295   -2.2275    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6703   -1.5520    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2357   -0.8508    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4111   -0.8765    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.8784   -1.5066    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1147   -1.1947    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4134   -1.6293    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2803   -2.2790    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0156    0.6032    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  6  0  0  0
  2  3  1  0  0  0  0
  3  4  1  6  0  0  0
  4  5  1  0  0  0  0
  5  6  1  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  2  0  0  0  0
  9 11  1  0  0  0  0
 11 12  2  0  0  0  0
  6 12  1  0  0  0  0
 13 12  1  6  0  0  0
  3 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
  2 15  1  0  0  0  0
 15 16  2  0  0  0  0
 11 17  1  0  0  0  0
  6 18  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0046552

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@@H]1[C@@H]2CC[C@]3(C)C=CC(=O)C(C)=C3[C@@H]2OC1=O

> <INCHI_IDENTIFIER>
InChI=1S/C15H18O3/c1-8-10-4-6-15(3)7-5-11(16)9(2)12(15)13(10)18-14(8)17/h5,7-8,10,13H,4,6H2,1-3H3/t8-,10+,13-,15-/m1/s1

> <INCHI_KEY>
XJHDMGJURBVLLE-FMBSFYNOSA-N

> <FORMULA>
C15H18O3

> <MOLECULAR_WEIGHT>
246.3016

> <EXACT_MASS>
246.125594442

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
25.97152856346199

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(3R,3aS,5aR,9bR)-3,5a,9-trimethyl-2H,3H,3aH,4H,5H,5aH,8H,9bH-naphtho[1,2-b]furan-2,8-dione

> <ALOGPS_LOGP>
1.98

> <JCHEM_LOGP>
2.6011767110000004

> <ALOGPS_LOGS>
-2.92

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-6.072499727460135

> <JCHEM_POLAR_SURFACE_AREA>
43.370000000000005

> <JCHEM_REFRACTIVITY>
68.8324

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.95e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(3R,3aS,5aR,9bR)-3,5a,9-trimethyl-3H,3aH,4H,5H,9bH-naphtho[1,2-b]furan-2,8-dione

> <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       2.884   0.300   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       4.060  -0.694   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       5.556  -0.327   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       6.284   1.030   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       7.823   1.078   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       8.634  -0.231   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      10.174  -0.183   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      10.985  -1.492   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      10.257  -2.849   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0      11.068  -4.158   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       8.718  -2.897   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       7.907  -1.588   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       6.367  -1.636   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       5.373  -2.812   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       3.947  -2.230   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       2.638  -3.041   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       7.990  -4.254   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       9.362   1.126   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   15                                                  
CONECT    3    2    4   13                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7   12   18                                             
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12   17                                                  
CONECT   12   11    6   13                                                  
CONECT   13   12    3   14                                                  
CONECT   14   13   15                                                       
CONECT   15   14    2   16                                                  
CONECT   16   15                                                            
CONECT   17   11                                                            
CONECT   18    6                                                            
MASTER        0    0    0    0    0    0    0    0   18    0   40    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₅H₁₈O₃

Average Mass

246.3016 Da

Monoisotopic Mass

246.12559 Da

IUPAC Name

(3R,3aS,5aR,9bR)-3,5a,9-trimethyl-2H,3H,3aH,4H,5H,5aH,8H,9bH-naphtho[1,2-b]furan-2,8-dione

Traditional Name

(3R,3aS,5aR,9bR)-3,5a,9-trimethyl-3H,3aH,4H,5H,9bH-naphtho[1,2-b]furan-2,8-dione

CAS Registry Number

481-06-1

SMILES

C[C@@H]1[C@@H]2CC[C@]3(C)C=CC(=O)C(C)=C3[C@@H]2OC1=O

InChI Identifier

InChI=1S/C15H18O3/c1-8-10-4-6-15(3)7-5-11(16)9(2)12(15)13(10)18-14(8)17/h5,7-8,10,13H,4,6H2,1-3H3/t8-,10+,13-,15-/m1/s1

InChI Key

XJHDMGJURBVLLE-FMBSFYNOSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Apium graveolens var. dulce	FooDB	Alexander J. MacLeod, Glesni MacLeod, G. Subramanian. Volatile aroma constituents of celery. Phyt...
Artemisia annua	Plant	KNApSAcK
Artemisia caerulescens	Plant	KNApSAcK
Artemisia cina	Plant	KNApSAcK
Artemisia compacta	Plant	KNApSAcK
Artemisia finita	Plant	KNApSAcK
Artemisia schrenkiana	Plant	KNApSAcK
Artemisia spp.	Plant	KNApSAcK
Artemisia sublessingiana	Plant	KNApSAcK
Cinnamomum verum	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Piper nigrum L.	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Pyrus pyrifolia	FooDB	Gary R. Takeoka, Ron G. Buttery, and Robert A. Flath. Volatile Constituents of Asian Pear (Pyrus ...
Solanum tuberosum	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as eudesmanolides, secoeudesmanolides, and derivatives. These are terpenoids with a structure based on the eudesmanolide (a 3,5a,9-trimethyl-naphtho[1,2-b]furan-2-one derivative) or secoeudesmanolide (a 3,6-dimethyl-5-(pentan-2-yl)-1-benzofuran-2-one derivative) skeleton.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Terpene lactones

Direct Parent

Eudesmanolides, secoeudesmanolides, and derivatives

Alternative Parents

Substituents

Eudesmanolide
Sesquiterpenoid
Naphthofuran
Gamma butyrolactone
Tetrahydrofuran
Cyclic ketone
Lactone
Ketone
Carboxylic acid ester
Oxacycle
Organoheterocyclic compound
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Organic oxide
Organooxygen compound
Organic oxygen compound
Carbonyl group
Hydrocarbon derivative
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic 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	1.98	ALOGPS
logP	2.6	ChemAxon
logS	-2.9	ALOGPS
pKa (Strongest Basic)	-6.1	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	43.37 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	68.83 m³·mol⁻¹	ChemAxon
Polarizability	25.97 Å³	ChemAxon
Number of Rings	3	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

FDB004902

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Sesquiterpene

METLIN ID

Not Available

PubChem Compound

667450

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Sesquiterpenes (NP0046552)

MOL for NP0046552 (Sesquiterpenes)

3D MOL for NP0046552 (Sesquiterpenes)

3D SDF for NP0046552 (Sesquiterpenes)

3D-SDF for NP0046552 (Sesquiterpenes)

PDB for NP0046552 (Sesquiterpenes)

3D PDB for NP0046552 (Sesquiterpenes)

SMILES for NP0046552 (Sesquiterpenes)

INCHI for NP0046552 (Sesquiterpenes)

Structure for NP0046552 (Sesquiterpenes)

3D Structure for NP0046552 (Sesquiterpenes)