NP-MRD: Showing NP-Card for 9-ethynyl-3-hydroxy-8-methoxy-4,4,6a,10,11b-pentamethyl-1h,2h,3h,4ah,5h,11h,11ah-cyclohexa[a]fluoren-6-one (NP0244986)

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Record Information

Version

2.0

Created at

2022-09-07 05:54:30 UTC

Updated at

2022-09-07 05:54:30 UTC

NP-MRD ID

NP0244986

Secondary Accession Numbers

None

Natural Product Identification

Common Name

9-ethynyl-3-hydroxy-8-methoxy-4,4,6a,10,11b-pentamethyl-1h,2h,3h,4ah,5h,11h,11ah-cyclohexa[a]fluoren-6-one

Description

14-Ethynyl-5-hydroxy-13-methoxy-2,6,6,10,15-pentamethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁶]Heptadeca-11,13,15-trien-9-one belongs to the class of organic compounds known as fluorenes. Fluorenes are compounds containing a fluorene moiety, which consists of two benzene rings connected through either a cyclopentane, cyclopentene, or cyclopenta-1,3-diene. 14-Ethynyl-5-hydroxy-13-methoxy-2,6,6,10,15-pentamethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁶]Heptadeca-11,13,15-trien-9-one is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL SDF PDB SMILES InChI


  Mrv1533004171512442D          

 28 31  0  0  0  0            999 V2000
   -1.1995   -3.7245    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4663   -4.1026    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2278   -3.6566    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9611   -4.0347    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6551   -3.5887    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6159   -2.7647    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3875   -2.4727    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9036   -3.1164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7273   -3.1635    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3563   -2.4266    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1799   -2.4738    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0036   -2.5209    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3746   -3.2578    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1982   -3.3049    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9219   -3.9475    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6798   -4.2735    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7325   -4.7505    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0983   -3.9004    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6456   -4.5901    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8220   -4.5430    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3693   -5.2327    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4510   -3.8061    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9287   -4.4447    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8826   -2.3866    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8434   -1.5625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1886   -2.8326    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5447   -2.4545    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2779   -2.0764    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  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  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  1  0  0  0  0
  9 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  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
 15 18  1  0  0  0  0
  9 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 20 22  1  0  0  0  0
  5 22  1  0  0  0  0
  8 22  1  0  0  0  0
 22 23  1  0  0  0  0
  6 24  1  0  0  0  0
 24 25  1  0  0  0  0
 24 26  2  0  0  0  0
  3 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  3  0  0  0  0
M  END


  Mrv1533004171512442D          

 28 31  0  0  0  0            999 V2000
   -1.1995   -3.7245    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4663   -4.1026    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2278   -3.6566    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9611   -4.0347    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6551   -3.5887    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6159   -2.7647    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3875   -2.4727    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9036   -3.1164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7273   -3.1635    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3563   -2.4266    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1799   -2.4738    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0036   -2.5209    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3746   -3.2578    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1982   -3.3049    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9219   -3.9475    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6798   -4.2735    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7325   -4.7505    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0983   -3.9004    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6456   -4.5901    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8220   -4.5430    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3693   -5.2327    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4510   -3.8061    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9287   -4.4447    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8826   -2.3866    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8434   -1.5625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1886   -2.8326    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5447   -2.4545    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2779   -2.0764    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  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  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  1  0  0  0  0
  9 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  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
 15 18  1  0  0  0  0
  9 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 20 22  1  0  0  0  0
  5 22  1  0  0  0  0
  8 22  1  0  0  0  0
 22 23  1  0  0  0  0
  6 24  1  0  0  0  0
 24 25  1  0  0  0  0
 24 26  2  0  0  0  0
  3 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  3  0  0  0  0
M  END
> <DATABASE_ID>
NP0244986

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC2=C(CC3C2(C)C(=O)CC2C(C)(C)C(O)CCC32C)C(C)=C1C#C

> <INCHI_IDENTIFIER>
InChI=1S/C25H32O3/c1-8-15-14(2)16-11-20-24(5)10-9-21(26)23(3,4)19(24)13-22(27)25(20,6)17(16)12-18(15)28-7/h1,12,19-21,26H,9-11,13H2,2-7H3

> <INCHI_KEY>
NYQLNNYPSKJEBN-UHFFFAOYSA-N

> <FORMULA>
C25H32O3

> <MOLECULAR_WEIGHT>
380.528

> <EXACT_MASS>
380.23514489

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
60

> <JCHEM_AVERAGE_POLARIZABILITY>
44.48862290801026

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
14-ethynyl-5-hydroxy-13-methoxy-2,6,6,10,15-pentamethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁶]heptadeca-11(16),12,14-trien-9-one

> <ALOGPS_LOGP>
4.47

> <JCHEM_LOGP>
4.775482039333335

> <ALOGPS_LOGS>
-5.24

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
19.554117064544624

> <JCHEM_PKA_STRONGEST_ACIDIC>
19.37170167322767

> <JCHEM_PKA_STRONGEST_BASIC>
-0.8067909859923724

> <JCHEM_POLAR_SURFACE_AREA>
46.53

> <JCHEM_REFRACTIVITY>
108.79249999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.20e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
14-ethynyl-5-hydroxy-13-methoxy-2,6,6,10,15-pentamethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁶]heptadeca-11(16),12,14-trien-9-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 17-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   17-APR-15         0                                  
HETATM    1  C   UNK     0      -2.239  -6.952   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      -0.870  -7.658   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       0.425  -6.826   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.794  -7.531   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       3.090  -6.699   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       3.016  -5.161   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.457  -4.616   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       5.420  -5.817   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       6.958  -5.905   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       6.265  -4.530   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       7.803  -4.618   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       9.340  -4.706   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      10.033  -6.081   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0      11.570  -6.169   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       9.188  -7.369   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      10.602  -7.977   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       8.834  -8.868   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       7.650  -7.281   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       6.805  -8.568   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       5.268  -8.480   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       4.423  -9.768   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       4.575  -7.105   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       3.600  -8.297   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       1.648  -4.455   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       1.574  -2.917   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       0.352  -5.287   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      -1.017  -4.582   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      -2.385  -3.876   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   26                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6   22                                                  
CONECT    6    5    7   24                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   22                                                  
CONECT    9    8   10   11   18                                             
CONECT   10    9                                                            
CONECT   11    9   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13   16   17   18                                             
CONECT   16   15                                                            
CONECT   17   15                                                            
CONECT   18   15    9   19                                                  
CONECT   19   18   20                                                       
CONECT   20   19   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20    5    8   23                                             
CONECT   23   22                                                            
CONECT   24    6   25   26                                                  
CONECT   25   24                                                            
CONECT   26   24    3   27                                                  
CONECT   27   26   28                                                       
CONECT   28   27                                                            
MASTER        0    0    0    0    0    0    0    0   28    0   62    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₅H₃₂O₃

Average Mass

380.5280 Da

Monoisotopic Mass

380.23514 Da

IUPAC Name

14-ethynyl-5-hydroxy-13-methoxy-2,6,6,10,15-pentamethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁶]heptadeca-11(16),12,14-trien-9-one

Traditional Name

14-ethynyl-5-hydroxy-13-methoxy-2,6,6,10,15-pentamethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁶]heptadeca-11(16),12,14-trien-9-one

CAS Registry Number

Not Available

SMILES

COC1=CC2=C(CC3C2(C)C(=O)CC2C(C)(C)C(O)CCC32C)C(C)=C1C#C

InChI Identifier

InChI=1S/C25H32O3/c1-8-15-14(2)16-11-20-24(5)10-9-21(26)23(3,4)19(24)13-22(27)25(20,6)17(16)12-18(15)28-7/h1,12,19-21,26H,9-11,13H2,2-7H3

InChI Key

NYQLNNYPSKJEBN-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 fluorenes. Fluorenes are compounds containing a fluorene moiety, which consists of two benzene rings connected through either a cyclopentane, cyclopentene, or cyclopenta-1,3-diene.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Fluorenes

Sub Class

Not Available

Direct Parent

Fluorenes

Alternative Parents

Substituents

Fluorene
Indane
Anisole
Alkyl aryl ether
Cyclic alcohol
Secondary alcohol
Ketone
Acetylide
Ether
Alcohol
Organooxygen compound
Hydrocarbon derivative
Carbonyl group
Organic oxide
Organic oxygen compound
Aromatic homopolycyclic compound

Molecular Framework

Aromatic homopolycyclic 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	4.47	ALOGPS
logP	4.78	ChemAxon
logS	-5.2	ALOGPS
pKa (Strongest Acidic)	19.37	ChemAxon
pKa (Strongest Basic)	-0.81	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	46.53 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	108.79 m³·mol⁻¹	ChemAxon
Polarizability	44.49 Å³	ChemAxon
Number of Rings	4	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 9-ethynyl-3-hydroxy-8-methoxy-4,4,6a,10,11b-pentamethyl-1h,2h,3h,4ah,5h,11h,11ah-cyclohexa[a]fluoren-6-one (NP0244986)

MOL for NP0244986 (9-ethynyl-3-hydroxy-8-methoxy-4,4,6a,10,11b-pentamethyl-1h,2h,3h,4ah,5h,11h,11ah-cyclohexa[a]fluoren-6-one)

3D MOL for NP0244986 (9-ethynyl-3-hydroxy-8-methoxy-4,4,6a,10,11b-pentamethyl-1h,2h,3h,4ah,5h,11h,11ah-cyclohexa[a]fluoren-6-one)

3D SDF for NP0244986 (9-ethynyl-3-hydroxy-8-methoxy-4,4,6a,10,11b-pentamethyl-1h,2h,3h,4ah,5h,11h,11ah-cyclohexa[a]fluoren-6-one)

3D-SDF for NP0244986 (9-ethynyl-3-hydroxy-8-methoxy-4,4,6a,10,11b-pentamethyl-1h,2h,3h,4ah,5h,11h,11ah-cyclohexa[a]fluoren-6-one)

PDB for NP0244986 (9-ethynyl-3-hydroxy-8-methoxy-4,4,6a,10,11b-pentamethyl-1h,2h,3h,4ah,5h,11h,11ah-cyclohexa[a]fluoren-6-one)

3D PDB for NP0244986 (9-ethynyl-3-hydroxy-8-methoxy-4,4,6a,10,11b-pentamethyl-1h,2h,3h,4ah,5h,11h,11ah-cyclohexa[a]fluoren-6-one)

SMILES for NP0244986 (9-ethynyl-3-hydroxy-8-methoxy-4,4,6a,10,11b-pentamethyl-1h,2h,3h,4ah,5h,11h,11ah-cyclohexa[a]fluoren-6-one)

INCHI for NP0244986 (9-ethynyl-3-hydroxy-8-methoxy-4,4,6a,10,11b-pentamethyl-1h,2h,3h,4ah,5h,11h,11ah-cyclohexa[a]fluoren-6-one)

Structure for NP0244986 (9-ethynyl-3-hydroxy-8-methoxy-4,4,6a,10,11b-pentamethyl-1h,2h,3h,4ah,5h,11h,11ah-cyclohexa[a]fluoren-6-one)

3D Structure for NP0244986 (9-ethynyl-3-hydroxy-8-methoxy-4,4,6a,10,11b-pentamethyl-1h,2h,3h,4ah,5h,11h,11ah-cyclohexa[a]fluoren-6-one)