NP-MRD: Showing NP-Card for (1r,8r,15s)-3,15-dimethyl-5,14-dioxatetracyclo[6.6.1.0²,⁶.0¹²,¹⁵]pentadeca-2(6),3,11-trien-13-one (NP0291408)

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Record Information

Version

1.0

Created at

2022-09-09 22:29:14 UTC

Updated at

2022-09-09 22:29:14 UTC

NP-MRD ID

NP0291408

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1r,8r,15s)-3,15-dimethyl-5,14-dioxatetracyclo[6.6.1.0²,⁶.0¹²,¹⁵]pentadeca-2(6),3,11-trien-13-one

Description

4Alpha-Hydroxy-3,4abeta-dimethyl-4,4a,7,8,8abeta,9-hexahydronaphtho[2,3-b]furan-5-carboxylic acid lactone belongs to the class of organic compounds known as naphthofurans. Naphthofurans are compounds containing a furan ring fused to a naphthalene moiety. Furan is a 5 membered- ring aromatic ring with four carbon and one oxygen atoms. Naphthalene is a polycyclic aromatic hydrocarbon made up of two fused benzene rings. (1r,8r,15s)-3,15-dimethyl-5,14-dioxatetracyclo[6.6.1.0²,⁶.0¹²,¹⁵]pentadeca-2(6),3,11-trien-13-one is found in Ligularia atroviolacea and Ligularia tongolensis. Based on a literature review very few articles have been published on 4alpha-Hydroxy-3,4abeta-dimethyl-4,4a,7,8,8abeta,9-hexahydronaphtho[2,3-b]furan-5-carboxylic acid lactone.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652309102200292D          

 18 21  0  0  1  0            999 V2000
    4.7518   -0.3388    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5413    0.4589    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0629    1.0981    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6161    1.7917    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8184    1.5811    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7722    0.7574    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0357    0.3856    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.8192   -0.4105    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9952   -0.4506    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5433   -1.1408    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7024    0.3207    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9333    0.6192    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8073    1.4346    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4504    1.9514    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3917    1.6612    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.1282    2.0330    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3455    0.8375    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.6118    1.2148    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  2  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  6  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
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 15 14  1  6  0  0  0
 15 16  1  0  0  0  0
  5 16  1  0  0  0  0
 15 17  1  0  0  0  0
 11 17  1  0  0  0  0
  7 17  1  0  0  0  0
 17 18  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0291408

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1=COC2=C1[C@@H]1OC(=O)C3=CCC[C@H](C2)[C@]13C

> <INCHI_IDENTIFIER>
InChI=1S/C15H16O3/c1-8-7-17-11-6-9-4-3-5-10-14(16)18-13(12(8)11)15(9,10)2/h5,7,9,13H,3-4,6H2,1-2H3/t9-,13+,15+/m1/s1

> <INCHI_KEY>
KROCVIWNITXTIQ-DVJZZOLTSA-N

> <FORMULA>
C15H16O3

> <MOLECULAR_WEIGHT>
244.29

> <EXACT_MASS>
244.109944375

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_ATOM_COUNT>
34

> <JCHEM_AVERAGE_POLARIZABILITY>
25.787060341144773

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1R,8R,15S)-3,15-dimethyl-5,14-dioxatetracyclo[6.6.1.0^{2,6}.0^{12,15}]pentadeca-2(6),3,11-trien-13-one

> <JCHEM_LOGP>
3.0387904003333333

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-2.727104949829043

> <JCHEM_POLAR_SURFACE_AREA>
39.44

> <JCHEM_REFRACTIVITY>
67.0835

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(1R,8R,15S)-3,15-dimethyl-5,14-dioxatetracyclo[6.6.1.0^{2,6}.0^{12,15}]pentadeca-2(6),3,11-trien-13-one

> <JCHEM_VEBER_RULE>
1

$$$$

HEADER    PROTEIN                                 10-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   10-SEP-22         0                                  
HETATM    1  C   UNK     0       8.870  -0.632   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       8.477   0.857   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       9.451   2.050   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       8.617   3.344   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       7.128   2.951   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       7.041   1.414   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       5.667   0.720   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       5.263  -0.766   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       3.724  -0.841   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       2.881  -2.130   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       3.178   0.599   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.742   1.156   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.507   2.678   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.707   3.643   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.465   3.101   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       5.839   3.795   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       4.378   1.563   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       3.009   2.268   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    6                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6   16                                                  
CONECT    6    5    2    7                                                  
CONECT    7    6    8   17                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12   17                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16   17                                                  
CONECT   16   15    5                                                       
CONECT   17   15   11    7   18                                             
CONECT   18   17                                                            
MASTER        0    0    0    0    0    0    0    0   18    0   42    0
END

View in JSmol

Synonyms

Value	Source
4a-Hydroxy-3,4abeta-dimethyl-4,4a,7,8,8abeta,9-hexahydronaphtho[2,3-b]furan-5-carboxylate lactone	Generator
4a-Hydroxy-3,4abeta-dimethyl-4,4a,7,8,8abeta,9-hexahydronaphtho[2,3-b]furan-5-carboxylic acid lactone	Generator
4alpha-Hydroxy-3,4abeta-dimethyl-4,4a,7,8,8abeta,9-hexahydronaphtho[2,3-b]furan-5-carboxylate lactone	Generator
4Α-hydroxy-3,4abeta-dimethyl-4,4a,7,8,8abeta,9-hexahydronaphtho[2,3-b]furan-5-carboxylate lactone	Generator
4Α-hydroxy-3,4abeta-dimethyl-4,4a,7,8,8abeta,9-hexahydronaphtho[2,3-b]furan-5-carboxylic acid lactone	Generator

Chemical Formula

C₁₅H₁₆O₃

Average Mass

244.2900 Da

Monoisotopic Mass

244.10994 Da

IUPAC Name

(1R,8R,15S)-3,15-dimethyl-5,14-dioxatetracyclo[6.6.1.0^{2,6}.0^{12,15}]pentadeca-2(6),3,11-trien-13-one

Traditional Name

(1R,8R,15S)-3,15-dimethyl-5,14-dioxatetracyclo[6.6.1.0^{2,6}.0^{12,15}]pentadeca-2(6),3,11-trien-13-one

CAS Registry Number

Not Available

SMILES

CC1=COC2=C1[C@@H]1OC(=O)C3=CCC[C@H](C2)[C@]13C

InChI Identifier

InChI=1S/C15H16O3/c1-8-7-17-11-6-9-4-3-5-10-14(16)18-13(12(8)11)15(9,10)2/h5,7,9,13H,3-4,6H2,1-2H3/t9-,13+,15+/m1/s1

InChI Key

KROCVIWNITXTIQ-DVJZZOLTSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Ligularia atroviolacea	LOTUS Database	35616633
Ligularia tongolensis	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as naphthofurans. Naphthofurans are compounds containing a furan ring fused to a naphthalene moiety. Furan is a 5 membered- ring aromatic ring with four carbon and one oxygen atoms. Naphthalene is a polycyclic aromatic hydrocarbon made up of two fused benzene rings.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Naphthofurans

Sub Class

Not Available

Direct Parent

Naphthofurans

Alternative Parents

Substituents

Naphthofuran
Benzofuran
Gamma butyrolactone
Furan
Oxolane
Enoate ester
Alpha,beta-unsaturated carboxylic ester
Heteroaromatic compound
Lactone
Carboxylic acid ester
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Oxacycle
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Carbonyl group
Aromatic heteropolycyclic compound

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	3.04	ChemAxon
pKa (Strongest Basic)	-2.7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	39.44 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	67.08 m³·mol⁻¹	ChemAxon
Polarizability	25.79 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

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

101267857

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (1r,8r,15s)-3,15-dimethyl-5,14-dioxatetracyclo[6.6.1.0²,⁶.0¹²,¹⁵]pentadeca-2(6),3,11-trien-13-one (NP0291408)

MOL for NP0291408 ((1r,8r,15s)-3,15-dimethyl-5,14-dioxatetracyclo[6.6.1.0²,⁶.0¹²,¹⁵]pentadeca-2(6),3,11-trien-13-one)

3D MOL for NP0291408 ((1r,8r,15s)-3,15-dimethyl-5,14-dioxatetracyclo[6.6.1.0²,⁶.0¹²,¹⁵]pentadeca-2(6),3,11-trien-13-one)

3D SDF for NP0291408 ((1r,8r,15s)-3,15-dimethyl-5,14-dioxatetracyclo[6.6.1.0²,⁶.0¹²,¹⁵]pentadeca-2(6),3,11-trien-13-one)

3D-SDF for NP0291408 ((1r,8r,15s)-3,15-dimethyl-5,14-dioxatetracyclo[6.6.1.0²,⁶.0¹²,¹⁵]pentadeca-2(6),3,11-trien-13-one)

PDB for NP0291408 ((1r,8r,15s)-3,15-dimethyl-5,14-dioxatetracyclo[6.6.1.0²,⁶.0¹²,¹⁵]pentadeca-2(6),3,11-trien-13-one)

3D PDB for NP0291408 ((1r,8r,15s)-3,15-dimethyl-5,14-dioxatetracyclo[6.6.1.0²,⁶.0¹²,¹⁵]pentadeca-2(6),3,11-trien-13-one)

SMILES for NP0291408 ((1r,8r,15s)-3,15-dimethyl-5,14-dioxatetracyclo[6.6.1.0²,⁶.0¹²,¹⁵]pentadeca-2(6),3,11-trien-13-one)

INCHI for NP0291408 ((1r,8r,15s)-3,15-dimethyl-5,14-dioxatetracyclo[6.6.1.0²,⁶.0¹²,¹⁵]pentadeca-2(6),3,11-trien-13-one)

Structure for NP0291408 ((1r,8r,15s)-3,15-dimethyl-5,14-dioxatetracyclo[6.6.1.0²,⁶.0¹²,¹⁵]pentadeca-2(6),3,11-trien-13-one)

3D Structure for NP0291408 ((1r,8r,15s)-3,15-dimethyl-5,14-dioxatetracyclo[6.6.1.0²,⁶.0¹²,¹⁵]pentadeca-2(6),3,11-trien-13-one)