NP-MRD: Showing NP-Card for 3a,7-dihydroxy-1,9,9a-trimethyl-1h,4h,5h,7h,8h,9h,9bh-naphtho[2,1-b]furan-2-one (NP0233301)

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Record Information

Version

2.0

Created at

2022-09-06 14:51:15 UTC

Updated at

2022-09-06 14:51:15 UTC

NP-MRD ID

NP0233301

Secondary Accession Numbers

None

Natural Product Identification

Common Name

3a,7-dihydroxy-1,9,9a-trimethyl-1h,4h,5h,7h,8h,9h,9bh-naphtho[2,1-b]furan-2-one

Description

3A,7-dihydroxy-1,9,9a-trimethyl-1H,2H,3aH,4H,5H,7H,8H,9H,9aH,9bH-naphtho[2,1-b]furan-2-one belongs to the class of organic compounds known as terpene lactones. These are prenol lipids containing a lactone ring. 3a,7-dihydroxy-1,9,9a-trimethyl-1h,4h,5h,7h,8h,9h,9bh-naphtho[2,1-b]furan-2-one is found in Rhytisma fulvum. 3A,7-dihydroxy-1,9,9a-trimethyl-1H,2H,3aH,4H,5H,7H,8H,9H,9aH,9bH-naphtho[2,1-b]furan-2-one is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL SDF PDB SMILES InChI


  Mrv1533004191516032D          

 19 21  0  0  0  0            999 V2000
    2.2089   -2.2790    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8189   -1.5520    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9943   -1.5262    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6043   -0.7992    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2203   -0.7735    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0390   -0.0980    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8636   -0.1238    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2982    0.5775    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1228    0.5517    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5127   -0.1753    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0183    0.4767    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3140   -0.3719    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3745   -1.1947    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0758   -1.6293    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6108   -1.5066    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4141   -2.3078    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0781   -0.8765    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2535   -0.8508    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6435   -1.5778    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
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  4  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 10 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 13 15  1  0  0  0  0
 15 16  1  0  0  0  0
 15 17  1  0  0  0  0
 10 17  1  0  0  0  0
 17 18  1  0  0  0  0
  2 18  1  0  0  0  0
  7 18  1  0  0  0  0
 18 19  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0233301

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1C2C(O)(CCC3=CC(O)CC(C)C23C)OC1=O

> <INCHI_IDENTIFIER>
InChI=1S/C15H22O4/c1-8-6-11(16)7-10-4-5-15(18)12(14(8,10)3)9(2)13(17)19-15/h7-9,11-12,16,18H,4-6H2,1-3H3

> <INCHI_KEY>
JKTAMRQCOYUPQI-UHFFFAOYSA-N

> <FORMULA>
C15H22O4

> <MOLECULAR_WEIGHT>
266.337

> <EXACT_MASS>
266.151809188

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
41

> <JCHEM_AVERAGE_POLARIZABILITY>
28.20712027982524

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
3a,7-dihydroxy-1,9,9a-trimethyl-1H,2H,3aH,4H,5H,7H,8H,9H,9aH,9bH-naphtho[2,1-b]furan-2-one

> <ALOGPS_LOGP>
1.56

> <JCHEM_LOGP>
1.3948396396666678

> <ALOGPS_LOGS>
-1.89

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
17.8246719059841

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.629599220183547

> <JCHEM_PKA_STRONGEST_BASIC>
-1.5632874145472044

> <JCHEM_POLAR_SURFACE_AREA>
66.75999999999999

> <JCHEM_REFRACTIVITY>
70.61489999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.47e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3a,7-dihydroxy-1,9,9a-trimethyl-1H,4H,5H,7H,8H,9H,9bH-naphtho[2,1-b]furan-2-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 19-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   19-APR-15         0                                  
HETATM    1  C   UNK     0       4.123  -4.254   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       3.395  -2.897   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.856  -2.849   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.128  -1.492   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0      -0.411  -1.444   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       1.939  -0.183   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       3.479  -0.231   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.290   1.078   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.829   1.030   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       6.557  -0.327   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       7.501   0.890   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0       8.053  -0.694   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       8.166  -2.230   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       9.475  -3.041   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       6.740  -2.812   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       6.373  -4.308   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       5.746  -1.636   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       4.207  -1.588   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       4.935  -2.945   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   18                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7                                                       
CONECT    7    6    8   18                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11   12   17                                             
CONECT   11   10                                                            
CONECT   12   10   13                                                       
CONECT   13   12   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15   10   18                                                  
CONECT   18   17    2    7   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

C₁₅H₂₂O₄

Average Mass

266.3370 Da

Monoisotopic Mass

266.15181 Da

IUPAC Name

3a,7-dihydroxy-1,9,9a-trimethyl-1H,2H,3aH,4H,5H,7H,8H,9H,9aH,9bH-naphtho[2,1-b]furan-2-one

Traditional Name

3a,7-dihydroxy-1,9,9a-trimethyl-1H,4H,5H,7H,8H,9H,9bH-naphtho[2,1-b]furan-2-one

CAS Registry Number

Not Available

SMILES

CC1C2C(O)(CCC3=CC(O)CC(C)C23C)OC1=O

InChI Identifier

InChI=1S/C15H22O4/c1-8-6-11(16)7-10-4-5-15(18)12(14(8,10)3)9(2)13(17)19-15/h7-9,11-12,16,18H,4-6H2,1-3H3

InChI Key

JKTAMRQCOYUPQI-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Rhytisma fulvum	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as terpene lactones. These are prenol lipids containing a lactone ring.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Terpene lactones

Direct Parent

Terpene lactones

Alternative Parents

Substituents

Terpene lactone
Sesquiterpenoid
Nardosinane sesquiterpenoid
Naphthofuran
Gamma butyrolactone
Cyclic alcohol
Tetrahydrofuran
Secondary alcohol
Lactone
Hemiacetal
Carboxylic acid ester
Oxacycle
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Organoheterocyclic compound
Hydrocarbon derivative
Organooxygen compound
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	1.56	ALOGPS
logP	1.39	ChemAxon
logS	-1.9	ALOGPS
pKa (Strongest Acidic)	11.63	ChemAxon
pKa (Strongest Basic)	-1.6	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	70.61 m³·mol⁻¹	ChemAxon
Polarizability	28.21 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

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 3a,7-dihydroxy-1,9,9a-trimethyl-1h,4h,5h,7h,8h,9h,9bh-naphtho[2,1-b]furan-2-one (NP0233301)

MOL for NP0233301 (3a,7-dihydroxy-1,9,9a-trimethyl-1h,4h,5h,7h,8h,9h,9bh-naphtho[2,1-b]furan-2-one)

3D MOL for NP0233301 (3a,7-dihydroxy-1,9,9a-trimethyl-1h,4h,5h,7h,8h,9h,9bh-naphtho[2,1-b]furan-2-one)

3D SDF for NP0233301 (3a,7-dihydroxy-1,9,9a-trimethyl-1h,4h,5h,7h,8h,9h,9bh-naphtho[2,1-b]furan-2-one)

3D-SDF for NP0233301 (3a,7-dihydroxy-1,9,9a-trimethyl-1h,4h,5h,7h,8h,9h,9bh-naphtho[2,1-b]furan-2-one)

PDB for NP0233301 (3a,7-dihydroxy-1,9,9a-trimethyl-1h,4h,5h,7h,8h,9h,9bh-naphtho[2,1-b]furan-2-one)

3D PDB for NP0233301 (3a,7-dihydroxy-1,9,9a-trimethyl-1h,4h,5h,7h,8h,9h,9bh-naphtho[2,1-b]furan-2-one)

SMILES for NP0233301 (3a,7-dihydroxy-1,9,9a-trimethyl-1h,4h,5h,7h,8h,9h,9bh-naphtho[2,1-b]furan-2-one)

INCHI for NP0233301 (3a,7-dihydroxy-1,9,9a-trimethyl-1h,4h,5h,7h,8h,9h,9bh-naphtho[2,1-b]furan-2-one)

Structure for NP0233301 (3a,7-dihydroxy-1,9,9a-trimethyl-1h,4h,5h,7h,8h,9h,9bh-naphtho[2,1-b]furan-2-one)

3D Structure for NP0233301 (3a,7-dihydroxy-1,9,9a-trimethyl-1h,4h,5h,7h,8h,9h,9bh-naphtho[2,1-b]furan-2-one)