NP-MRD: Showing NP-Card for Verboccidentafuran 4alpha,5alpha-epoxide (NP0063361)

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Record Information

Version

2.0

Created at

2022-04-28 07:47:26 UTC

Updated at

2022-04-28 07:47:26 UTC

NP-MRD ID

NP0063361

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Verboccidentafuran 4alpha,5alpha-epoxide

Description

(1R,8S,9R,12R,14R)-3,8,12-trimethyl-5,13-dioxatetracyclo[7.5.0.0²,⁶.0¹²,¹⁴]Tetradeca-2(6),3-diene 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. Verboccidentafuran 4alpha,5alpha-epoxide is found in Baccharis salicifolia . Based on a literature review very few articles have been published on (1R,8S,9R,12R,14R)-3,8,12-trimethyl-5,13-dioxatetracyclo[7.5.0.0²,⁶.0¹²,¹⁴]Tetradeca-2(6),3-diene.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652304282209472D          

 17 20  0  0  1  0            999 V2000
    2.9183    1.9063    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.0102    2.7262    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3461    3.2157    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5902    2.8854    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4983    2.0655    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.1623    1.5760    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.8264    1.0865    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7423    1.7352    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0782    2.2247    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1701    3.0446    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9261    3.3749    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.0180    4.1948    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5926    1.7444    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3431    0.9580    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4819    0.9523    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9622    0.2816    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7382    1.8144    0.0000 C   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
  4  3  1  1  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  1  6  1  0  0  0  0
  6  7  1  6  0  0  0
  1  7  1  0  0  0  0
  5  8  1  1  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
  4 11  1  0  0  0  0
 11 12  1  6  0  0  0
  9 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
  8 15  1  0  0  0  0
 15 16  1  0  0  0  0
  1 17  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0063361

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@H]1CC2=C([C@@H]3[C@H]4O[C@]4(C)CC[C@H]13)C(C)=CO2

> <INCHI_IDENTIFIER>
InChI=1S/C15H20O2/c1-8-6-11-12(9(2)7-16-11)13-10(8)4-5-15(3)14(13)17-15/h7-8,10,13-14H,4-6H2,1-3H3/t8-,10+,13+,14+,15+/m0/s1

> <INCHI_KEY>
QMMCFHIZTWGESQ-QFJYNZAASA-N

> <FORMULA>
C15H20O2

> <MOLECULAR_WEIGHT>
232.323

> <EXACT_MASS>
232.146329884

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_ATOM_COUNT>
37

> <JCHEM_AVERAGE_POLARIZABILITY>
26.34910940587151

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1R,8S,9R,12R,14R)-3,8,12-trimethyl-5,13-dioxatetracyclo[7.5.0.0^{2,6}.0^{12,14}]tetradeca-2(6),3-diene

> <ALOGPS_LOGP>
3.48

> <JCHEM_LOGP>
3.1883411483333335

> <ALOGPS_LOGS>
-3.95

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-2.657160972339983

> <JCHEM_POLAR_SURFACE_AREA>
25.67

> <JCHEM_REFRACTIVITY>
66.254

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.59e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1R,8S,9R,12R,14R)-3,8,12-trimethyl-5,13-dioxatetracyclo[7.5.0.0^{2,6}.0^{12,14}]tetradeca-2(6),3-diene

> <JCHEM_VEBER_RULE>
1

$$$$

HEADER    PROTEIN                                 28-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   28-APR-22         0                                  
HETATM    1  C   UNK     0       5.447   3.559   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       5.619   5.089   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       4.379   6.003   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.968   5.386   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.797   3.856   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.036   2.942   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       5.276   2.028   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       1.386   3.239   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.146   4.153   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.318   5.683   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.729   6.300   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.900   7.830   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0      -1.106   3.256   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0      -0.640   1.788   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       0.900   1.778   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       1.796   0.526   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       6.978   3.387   0.000  0.00  0.00           C+0
CONECT    1    2    6    7   17                                             
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5   11                                                  
CONECT    5    4    6    8                                                  
CONECT    6    5    1    7                                                  
CONECT    7    6    1                                                       
CONECT    8    5    9   15                                                  
CONECT    9    8   10   13                                                  
CONECT   10    9   11                                                       
CONECT   11   10    4   12                                                  
CONECT   12   11                                                            
CONECT   13    9   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14    8   16                                                  
CONECT   16   15                                                            
CONECT   17    1                                                            
MASTER        0    0    0    0    0    0    0    0   17    0   40    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₅H₂₀O₂

Average Mass

232.3230 Da

Monoisotopic Mass

232.14633 Da

IUPAC Name

(1R,8S,9R,12R,14R)-3,8,12-trimethyl-5,13-dioxatetracyclo[7.5.0.0^{2,6}.0^{12,14}]tetradeca-2(6),3-diene

Traditional Name

(1R,8S,9R,12R,14R)-3,8,12-trimethyl-5,13-dioxatetracyclo[7.5.0.0^{2,6}.0^{12,14}]tetradeca-2(6),3-diene

CAS Registry Number

Not Available

SMILES

C[C@H]1CC2=C([C@@H]3[C@H]4O[C@]4(C)CC[C@H]13)C(C)=CO2

InChI Identifier

InChI=1S/C15H20O2/c1-8-6-11-12(9(2)7-16-11)13-10(8)4-5-15(3)14(13)17-15/h7-8,10,13-14H,4-6H2,1-3H3/t8-,10+,13+,14+,15+/m0/s1

InChI Key

QMMCFHIZTWGESQ-QFJYNZAASA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Baccharis salicifolia	Plant	KNApSAcK

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
Oxepane
Heteroaromatic compound
Furan
Oxacycle
Ether
Oxirane
Dialkyl ether
Organic oxygen compound
Hydrocarbon derivative
Organooxygen compound
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	3.48	ALOGPS
logP	3.19	ChemAxon
logS	-4	ALOGPS
pKa (Strongest Basic)	-2.7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	25.67 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	66.25 m³·mol⁻¹	ChemAxon
Polarizability	26.35 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

162928844

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Verboccidentafuran 4alpha,5alpha-epoxide (NP0063361)

MOL for NP0063361 (Verboccidentafuran 4alpha,5alpha-epoxide)

3D MOL for NP0063361 (Verboccidentafuran 4alpha,5alpha-epoxide)

3D SDF for NP0063361 (Verboccidentafuran 4alpha,5alpha-epoxide)

3D-SDF for NP0063361 (Verboccidentafuran 4alpha,5alpha-epoxide)

PDB for NP0063361 (Verboccidentafuran 4alpha,5alpha-epoxide)

3D PDB for NP0063361 (Verboccidentafuran 4alpha,5alpha-epoxide)

SMILES for NP0063361 (Verboccidentafuran 4alpha,5alpha-epoxide)

INCHI for NP0063361 (Verboccidentafuran 4alpha,5alpha-epoxide)

Structure for NP0063361 (Verboccidentafuran 4alpha,5alpha-epoxide)

3D Structure for NP0063361 (Verboccidentafuran 4alpha,5alpha-epoxide)