NP-MRD: Showing NP-Card for 1,3a-dihydroxy-6,6,9a-trimethyl-octahydronaphtho[1,2-c]furan-3-one (NP0226280)

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Record Information

Version

2.0

Created at

2022-09-06 05:15:52 UTC

Updated at

2022-09-06 05:15:52 UTC

NP-MRD ID

NP0226280

Secondary Accession Numbers

None

Natural Product Identification

Common Name

1,3a-dihydroxy-6,6,9a-trimethyl-octahydronaphtho[1,2-c]furan-3-one

Description

1,3A-dihydroxy-6,6,9a-trimethyl-dodecahydronaphtho[1,2-c]furan-3-one 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. 1,3A-dihydroxy-6,6,9a-trimethyl-dodecahydronaphtho[1,2-c]furan-3-one is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL SDF PDB SMILES InChI


  Mrv1533004251510392D          

 19 21  0  0  0  0            999 V2000
    5.5018   -0.6207    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7358   -0.3145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5672   -1.1221    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1704    0.3867    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7804    1.1137    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9558    1.1395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5212    0.4383    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1312    1.1653    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9112   -0.2887    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4766   -0.9900    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6520   -0.9642    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2620   -0.2372    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7565   -0.8892    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6966    0.4640    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1640    1.0941    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3606    1.8953    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4002    0.7822    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4608   -0.0406    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8307   -0.5732    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  4  1  0  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  1  0  0  0  0
  7  9  1  0  0  0  0
  2  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 12 14  1  0  0  0  0
  7 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 15 17  1  0  0  0  0
 17 18  1  0  0  0  0
 12 18  1  0  0  0  0
 18 19  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0226280

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1(C)CCCC2(C)C3C(O)OC(=O)C3(O)CCC12

> <INCHI_IDENTIFIER>
InChI=1S/C15H24O4/c1-13(2)6-4-7-14(3)9(13)5-8-15(18)10(14)11(16)19-12(15)17/h9-11,16,18H,4-8H2,1-3H3

> <INCHI_KEY>
GGWKVMGHNXNHGX-UHFFFAOYSA-N

> <FORMULA>
C15H24O4

> <MOLECULAR_WEIGHT>
268.353

> <EXACT_MASS>
268.167459253

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
43

> <JCHEM_AVERAGE_POLARIZABILITY>
29.047403175897518

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
1,3a-dihydroxy-6,6,9a-trimethyl-dodecahydronaphtho[1,2-c]furan-3-one

> <ALOGPS_LOGP>
1.92

> <JCHEM_LOGP>
2.248656687333332

> <ALOGPS_LOGS>
-2.24

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.369872208687976

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.647966021400329

> <JCHEM_PKA_STRONGEST_BASIC>
-4.114433700872996

> <JCHEM_POLAR_SURFACE_AREA>
66.75999999999999

> <JCHEM_REFRACTIVITY>
69.02809999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.56e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
1,3a-dihydroxy-6,6,9a-trimethyl-octahydronaphtho[1,2-c]furan-3-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 25-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   25-APR-15         0                                  
HETATM    1  C   UNK     0      10.270  -1.159   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       8.840  -0.587   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       8.525  -2.095   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       9.651   0.722   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       8.923   2.079   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       7.384   2.127   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.573   0.818   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       5.845   2.175   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       7.301  -0.539   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       6.490  -1.848   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.950  -1.800   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.222  -0.443   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       3.279  -1.660   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       5.034   0.866   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.039   2.042   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       4.406   3.538   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0       2.614   1.460   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       2.727  -0.076   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       1.551  -1.070   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    4    9                                             
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8    9   14                                             
CONECT    8    7                                                            
CONECT    9    7    2   10                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13   14   18                                             
CONECT   13   12                                                            
CONECT   14   12    7   15                                                  
CONECT   15   14   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15   18                                                       
CONECT   18   17   12   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

C₁₅H₂₄O₄

Average Mass

268.3530 Da

Monoisotopic Mass

268.16746 Da

IUPAC Name

1,3a-dihydroxy-6,6,9a-trimethyl-dodecahydronaphtho[1,2-c]furan-3-one

Traditional Name

1,3a-dihydroxy-6,6,9a-trimethyl-octahydronaphtho[1,2-c]furan-3-one

CAS Registry Number

Not Available

SMILES

CC1(C)CCCC2(C)C3C(O)OC(=O)C3(O)CCC12

InChI Identifier

InChI=1S/C15H24O4/c1-13(2)6-4-7-14(3)9(13)5-8-15(18)10(14)11(16)19-12(15)17/h9-11,16,18H,4-8H2,1-3H3

InChI Key

GGWKVMGHNXNHGX-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Not Available

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
Gamma butyrolactone
Cyclic alcohol
Tertiary alcohol
Tetrahydrofuran
Carboxylic acid ester
Hemiacetal
Lactone
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Oxacycle
Carbonyl group
Organic oxide
Organic oxygen compound
Alcohol
Hydrocarbon derivative
Organooxygen compound
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	1.92	ALOGPS
logP	2.25	ChemAxon
logS	-2.2	ALOGPS
pKa (Strongest Acidic)	11.65	ChemAxon
pKa (Strongest Basic)	-4.1	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	69.03 m³·mol⁻¹	ChemAxon
Polarizability	29.05 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

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

85409107

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 1,3a-dihydroxy-6,6,9a-trimethyl-octahydronaphtho[1,2-c]furan-3-one (NP0226280)

MOL for NP0226280 (1,3a-dihydroxy-6,6,9a-trimethyl-octahydronaphtho[1,2-c]furan-3-one)

3D MOL for NP0226280 (1,3a-dihydroxy-6,6,9a-trimethyl-octahydronaphtho[1,2-c]furan-3-one)

3D SDF for NP0226280 (1,3a-dihydroxy-6,6,9a-trimethyl-octahydronaphtho[1,2-c]furan-3-one)

3D-SDF for NP0226280 (1,3a-dihydroxy-6,6,9a-trimethyl-octahydronaphtho[1,2-c]furan-3-one)

PDB for NP0226280 (1,3a-dihydroxy-6,6,9a-trimethyl-octahydronaphtho[1,2-c]furan-3-one)

3D PDB for NP0226280 (1,3a-dihydroxy-6,6,9a-trimethyl-octahydronaphtho[1,2-c]furan-3-one)

SMILES for NP0226280 (1,3a-dihydroxy-6,6,9a-trimethyl-octahydronaphtho[1,2-c]furan-3-one)

INCHI for NP0226280 (1,3a-dihydroxy-6,6,9a-trimethyl-octahydronaphtho[1,2-c]furan-3-one)

Structure for NP0226280 (1,3a-dihydroxy-6,6,9a-trimethyl-octahydronaphtho[1,2-c]furan-3-one)

3D Structure for NP0226280 (1,3a-dihydroxy-6,6,9a-trimethyl-octahydronaphtho[1,2-c]furan-3-one)