NP-MRD: Showing NP-Card for Rothin B (NP0046780)

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Record Information

Version

2.0

Created at

2022-03-17 20:29:26 UTC

Updated at

2022-03-17 20:29:27 UTC

NP-MRD ID

NP0046780

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Rothin B

Description

Rothin B 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. Rothin B is found in Artemisia rothrockii and Artemisia tridentata. Rothin B is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL SDF PDB SMILES InChI


  Mrv0541 02241223402D          

 19 21  0  0  0  0            999 V2000
   -1.9430    0.2426    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1332    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9717   -0.8090    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1612   -1.1329    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8094   -1.7000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0808   -1.9434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7283   -2.2671    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3766   -1.7811    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2143   -0.9713    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9430   -0.6476    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2143    1.7007    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5668    1.2958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5668    0.4860    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2430    0.1615    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4857   -0.5664    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0528   -0.0811    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6479    0.8909    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2430    1.5385    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4857    2.2671    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
  2 13  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  4  6  1  0  0  0  0
  4 15  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
  9 15  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 12 18  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 14 17  1  0  0  0  0
 15 16  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0046780

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC12CCCC(=C)C1(O)C1OC(=O)C(=C)C1C(O)C2

> <INCHI_IDENTIFIER>
InChI=1S/C15H20O4/c1-8-5-4-6-14(3)7-10(16)11-9(2)13(17)19-12(11)15(8,14)18/h10-12,16,18H,1-2,4-7H2,3H3

> <INCHI_KEY>
CMVJNYSIDKGGLC-UHFFFAOYSA-N

> <FORMULA>
C15H20O4

> <MOLECULAR_WEIGHT>
264.3169

> <EXACT_MASS>
264.136159128

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
27.92395249008817

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
4,9a-dihydroxy-5a-methyl-3,9-dimethylidene-dodecahydronaphtho[1,2-b]furan-2-one

> <ALOGPS_LOGP>
0.89

> <JCHEM_LOGP>
1.3212361369999999

> <ALOGPS_LOGS>
-1.79

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.847297867027688

> <JCHEM_PKA_STRONGEST_ACIDIC>
6.302999093508956

> <JCHEM_PKA_STRONGEST_BASIC>
-2.9066168675496264

> <JCHEM_POLAR_SURFACE_AREA>
66.75999999999999

> <JCHEM_REFRACTIVITY>
68.83419999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.32e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
4,9a-dihydroxy-5a-methyl-3,9-dimethylidene-hexahydro-3aH-naphtho[1,2-b]furan-2-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  O   UNK     0      -3.627   0.453   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0      -2.115   0.000   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -1.814  -1.510   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -0.301  -2.115   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -1.511  -3.173   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.151  -3.628   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.359  -4.232   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.570  -3.325   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.267  -1.813   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       3.627  -1.209   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -2.267   3.175   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -1.058   2.419   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -1.058   0.907   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       0.454   0.301   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       0.907  -1.057   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       1.965  -0.151   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0       1.209   1.663   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       0.454   2.872   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       0.907   4.232   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   13                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5    6   15                                             
CONECT    5    4                                                            
CONECT    6    4    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   15                                                  
CONECT   10    9                                                            
CONECT   11   12                                                            
CONECT   12   11   13   18                                                  
CONECT   13    2   12   14                                                  
CONECT   14   13   15   17                                                  
CONECT   15    4    9   14   16                                             
CONECT   16   15                                                            
CONECT   17   14   18                                                       
CONECT   18   12   17   19                                                  
CONECT   19   18                                                            
MASTER        0    0    0    0    0    0    0    0   19    0   42    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₅H₂₀O₄

Average Mass

264.3169 Da

Monoisotopic Mass

264.13616 Da

IUPAC Name

4,9a-dihydroxy-5a-methyl-3,9-dimethylidene-dodecahydronaphtho[1,2-b]furan-2-one

Traditional Name

4,9a-dihydroxy-5a-methyl-3,9-dimethylidene-hexahydro-3aH-naphtho[1,2-b]furan-2-one

CAS Registry Number

Not Available

SMILES

CC12CCCC(=C)C1(O)C1OC(=O)C(=C)C1C(O)C2

InChI Identifier

InChI=1S/C15H20O4/c1-8-5-4-6-14(3)7-10(16)11-9(2)13(17)19-12(11)15(8,14)18/h10-12,16,18H,1-2,4-7H2,3H3

InChI Key

CMVJNYSIDKGGLC-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Artemisia rothrockii	Plant	KNApSAcK
Artemisia tridentata	LOTUS Database	35616633
Laurus nobilis L.	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
Cyclic alcohol
Tertiary alcohol
Tetrahydrofuran
Enoate ester
Alpha,beta-unsaturated carboxylic ester
Secondary alcohol
Lactone
Carboxylic acid ester
Oxacycle
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Organoheterocyclic compound
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Alcohol
Carbonyl group
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	0.89	ALOGPS
logP	1.32	ChemAxon
logS	-1.8	ALOGPS
pKa (Strongest Acidic)	6.3	ChemAxon
pKa (Strongest Basic)	-2.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	66.76 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	68.83 m³·mol⁻¹	ChemAxon
Polarizability	27.92 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

FDB005896

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

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Rothin B (NP0046780)

MOL for NP0046780 (Rothin B)

3D MOL for NP0046780 (Rothin B)

3D SDF for NP0046780 (Rothin B)

3D-SDF for NP0046780 (Rothin B)

PDB for NP0046780 (Rothin B)

3D PDB for NP0046780 (Rothin B)

SMILES for NP0046780 (Rothin B)

INCHI for NP0046780 (Rothin B)

Structure for NP0046780 (Rothin B)

3D Structure for NP0046780 (Rothin B)