NP-MRD: Showing NP-Card for 16-hydroxy-9-isopropyl-2,5,13,16-tetramethyl-6,15,19-trioxatetracyclo[12.5.1.0⁵,¹⁰.0¹⁷,²⁰]icosa-1,9,12-triene-7,18-dione (NP0160381)

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Record Information

Version

2.0

Created at

2022-09-02 18:19:43 UTC

Updated at

2022-09-02 18:19:43 UTC

NP-MRD ID

NP0160381

Secondary Accession Numbers

None

Natural Product Identification

Common Name

16-hydroxy-9-isopropyl-2,5,13,16-tetramethyl-6,15,19-trioxatetracyclo[12.5.1.0⁵,¹⁰.0¹⁷,²⁰]icosa-1,9,12-triene-7,18-dione

Description

16-Hydroxy-2,5,13,16-tetramethyl-9-(propan-2-yl)-6,15,19-trioxatetracyclo[12.5.1.0⁵,¹⁰.0¹⁷,²⁰]Icosa-1,9,12-triene-7,18-dione belongs to the class of organic compounds known as furofurans. These are organic compounds containing a two furan rings fused to each other. Furan is a five-membered aromatic ring with four carbon atoms and one oxygen atom. 16-Hydroxy-2,5,13,16-tetramethyl-9-(propan-2-yl)-6,15,19-trioxatetracyclo[12.5.1.0⁵,¹⁰.0¹⁷,²⁰]Icosa-1,9,12-triene-7,18-dione is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL SDF PDB SMILES InChI


  Mrv1533004161503102D          

 30 33  0  0  0  0            999 V2000
    7.1123   -1.7294    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5527   -1.1233    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7479   -1.3049    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7978   -0.3355    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2381    0.2706    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5502   -0.4931    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9204   -1.0259    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2190   -0.5915    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3907    0.2154    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3244   -0.7131    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7537   -1.3088    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0107   -0.9502    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7317   -1.7265    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2095   -0.7538    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1223   -0.1327    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7916   -0.0832    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0706    0.6931    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8825    0.8396    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6838    0.6433    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1616    1.6160    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9735    1.7625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4832    1.0584    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7747    1.8302    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2879    1.2400    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.8476    0.6339    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6524    0.8155    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.6025   -0.1539    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3028    1.1899    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7321    0.5941    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9146    0.7057    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  2  0  0  0  0
  5  6  1  0  0  0  0
  7  6  1  4  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  8 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
 12 15  1  0  0  0  0
 15 16  1  0  0  0  0
 10 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 18 19  1  4  0  0  0
 18 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
  5 22  1  0  0  0  0
 22 23  1  0  0  0  0
 22 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  2  0  0  0  0
 25 27  1  0  0  0  0
  4 27  1  0  0  0  0
 17 28  1  0  0  0  0
 28 29  1  0  0  0  0
 15 29  1  0  0  0  0
 29 30  2  0  0  0  0
M  END


  Mrv1533004161503102D          

 30 33  0  0  0  0            999 V2000
    7.1123   -1.7294    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5527   -1.1233    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7479   -1.3049    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7978   -0.3355    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2381    0.2706    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5502   -0.4931    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9204   -1.0259    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2190   -0.5915    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3907    0.2154    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3244   -0.7131    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7537   -1.3088    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0107   -0.9502    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7317   -1.7265    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2095   -0.7538    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1223   -0.1327    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7916   -0.0832    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0706    0.6931    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8825    0.8396    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6838    0.6433    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1616    1.6160    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9735    1.7625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4832    1.0584    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7747    1.8302    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2879    1.2400    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.8476    0.6339    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6524    0.8155    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.6025   -0.1539    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3028    1.1899    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7321    0.5941    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9146    0.7057    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  2  0  0  0  0
  5  6  1  0  0  0  0
  7  6  1  4  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  8 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
 12 15  1  0  0  0  0
 15 16  1  0  0  0  0
 10 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 18 19  1  4  0  0  0
 18 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
  5 22  1  0  0  0  0
 22 23  1  0  0  0  0
 22 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  2  0  0  0  0
 25 27  1  0  0  0  0
  4 27  1  0  0  0  0
 17 28  1  0  0  0  0
 28 29  1  0  0  0  0
 15 29  1  0  0  0  0
 29 30  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0160381

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)C1=C2CC=C(C)C3OC(C)(O)C4C3C(OC4=O)=C(C)CCC2(C)OC(=O)C1

> <INCHI_IDENTIFIER>
InChI=1S/C24H32O6/c1-12(2)15-11-17(25)29-23(5)10-9-14(4)20-18-19(22(26)28-20)24(6,27)30-21(18)13(3)7-8-16(15)23/h7,12,18-19,21,27H,8-11H2,1-6H3

> <INCHI_KEY>
YAEXNKPEJYCROB-UHFFFAOYSA-N

> <FORMULA>
C24H32O6

> <MOLECULAR_WEIGHT>
416.514

> <EXACT_MASS>
416.21988875

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
62

> <JCHEM_AVERAGE_POLARIZABILITY>
45.10804562085849

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
16-hydroxy-2,5,13,16-tetramethyl-9-(propan-2-yl)-6,15,19-trioxatetracyclo[12.5.1.0⁵,¹⁰.0¹⁷,²⁰]icosa-1,9,12-triene-7,18-dione

> <ALOGPS_LOGP>
3.93

> <JCHEM_LOGP>
2.7078759996666673

> <ALOGPS_LOGS>
-3.91

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.770807935692925

> <JCHEM_PKA_STRONGEST_BASIC>
-4.211248605607328

> <JCHEM_POLAR_SURFACE_AREA>
82.06

> <JCHEM_REFRACTIVITY>
113.36689999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.14e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
16-hydroxy-9-isopropyl-2,5,13,16-tetramethyl-6,15,19-trioxatetracyclo[12.5.1.0⁵,¹⁰.0¹⁷,²⁰]icosa-1,9,12-triene-7,18-dione

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 16-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   16-APR-15         0                                  
HETATM    1  C   UNK     0      13.276  -3.228   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      12.232  -2.097   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      10.729  -2.436   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      12.689  -0.626   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      11.644   0.505   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      12.227  -0.920   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      11.051  -1.915   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       9.742  -1.104   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      10.063   0.402   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       8.072  -1.331   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       7.007  -2.443   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       5.620  -1.774   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       5.099  -3.223   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       4.124  -1.407   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       5.828  -0.248   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       7.078  -0.155   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       7.599   1.294   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       9.114   1.567   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      10.610   1.201   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       9.635   3.017   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      11.150   3.290   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      12.102   1.976   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      12.646   3.416   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0      13.604   2.315   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0      14.649   1.183   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0      16.151   1.522   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0      14.191  -0.287   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0       6.165   2.221   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0       5.100   1.109   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0       3.574   1.317   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5   27                                                  
CONECT    5    4    6   22                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11   16                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13   14   15                                             
CONECT   13   12                                                            
CONECT   14   12                                                            
CONECT   15   12   16   29                                                  
CONECT   16   15   10   17                                                  
CONECT   17   16   18   28                                                  
CONECT   18   17   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21    5   23   24                                             
CONECT   23   22                                                            
CONECT   24   22   25                                                       
CONECT   25   24   26   27                                                  
CONECT   26   25                                                            
CONECT   27   25    4                                                       
CONECT   28   17   29                                                       
CONECT   29   28   15   30                                                  
CONECT   30   29                                                            
MASTER        0    0    0    0    0    0    0    0   30    0   66    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₄H₃₂O₆

Average Mass

416.5140 Da

Monoisotopic Mass

416.21989 Da

IUPAC Name

16-hydroxy-2,5,13,16-tetramethyl-9-(propan-2-yl)-6,15,19-trioxatetracyclo[12.5.1.0⁵,¹⁰.0¹⁷,²⁰]icosa-1,9,12-triene-7,18-dione

Traditional Name

16-hydroxy-9-isopropyl-2,5,13,16-tetramethyl-6,15,19-trioxatetracyclo[12.5.1.0⁵,¹⁰.0¹⁷,²⁰]icosa-1,9,12-triene-7,18-dione

CAS Registry Number

Not Available

SMILES

CC(C)C1=C2CC=C(C)C3OC(C)(O)C4C3C(OC4=O)=C(C)CCC2(C)OC(=O)C1

InChI Identifier

InChI=1S/C24H32O6/c1-12(2)15-11-17(25)29-23(5)10-9-14(4)20-18-19(22(26)28-20)24(6,27)30-21(18)13(3)7-8-16(15)23/h7,12,18-19,21,27H,8-11H2,1-6H3

InChI Key

YAEXNKPEJYCROB-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 furofurans. These are organic compounds containing a two furan rings fused to each other. Furan is a five-membered aromatic ring with four carbon atoms and one oxygen atom.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Furofurans

Sub Class

Not Available

Direct Parent

Furofurans

Alternative Parents

Substituents

Furofuran
Dihydropyranone
Dicarboxylic acid or derivatives
Pyran
Enol ester
Tetrahydrofuran
Lactone
Hemiacetal
Carboxylic acid ester
Carboxylic acid derivative
Oxacycle
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
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	3.93	ALOGPS
logP	2.71	ChemAxon
logS	-3.9	ALOGPS
pKa (Strongest Acidic)	11.77	ChemAxon
pKa (Strongest Basic)	-4.2	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	82.06 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	113.37 m³·mol⁻¹	ChemAxon
Polarizability	45.11 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 16-hydroxy-9-isopropyl-2,5,13,16-tetramethyl-6,15,19-trioxatetracyclo[12.5.1.0⁵,¹⁰.0¹⁷,²⁰]icosa-1,9,12-triene-7,18-dione (NP0160381)

MOL for NP0160381 (16-hydroxy-9-isopropyl-2,5,13,16-tetramethyl-6,15,19-trioxatetracyclo[12.5.1.0⁵,¹⁰.0¹⁷,²⁰]icosa-1,9,12-triene-7,18-dione)

3D MOL for NP0160381 (16-hydroxy-9-isopropyl-2,5,13,16-tetramethyl-6,15,19-trioxatetracyclo[12.5.1.0⁵,¹⁰.0¹⁷,²⁰]icosa-1,9,12-triene-7,18-dione)

3D SDF for NP0160381 (16-hydroxy-9-isopropyl-2,5,13,16-tetramethyl-6,15,19-trioxatetracyclo[12.5.1.0⁵,¹⁰.0¹⁷,²⁰]icosa-1,9,12-triene-7,18-dione)

3D-SDF for NP0160381 (16-hydroxy-9-isopropyl-2,5,13,16-tetramethyl-6,15,19-trioxatetracyclo[12.5.1.0⁵,¹⁰.0¹⁷,²⁰]icosa-1,9,12-triene-7,18-dione)

PDB for NP0160381 (16-hydroxy-9-isopropyl-2,5,13,16-tetramethyl-6,15,19-trioxatetracyclo[12.5.1.0⁵,¹⁰.0¹⁷,²⁰]icosa-1,9,12-triene-7,18-dione)

3D PDB for NP0160381 (16-hydroxy-9-isopropyl-2,5,13,16-tetramethyl-6,15,19-trioxatetracyclo[12.5.1.0⁵,¹⁰.0¹⁷,²⁰]icosa-1,9,12-triene-7,18-dione)

SMILES for NP0160381 (16-hydroxy-9-isopropyl-2,5,13,16-tetramethyl-6,15,19-trioxatetracyclo[12.5.1.0⁵,¹⁰.0¹⁷,²⁰]icosa-1,9,12-triene-7,18-dione)

INCHI for NP0160381 (16-hydroxy-9-isopropyl-2,5,13,16-tetramethyl-6,15,19-trioxatetracyclo[12.5.1.0⁵,¹⁰.0¹⁷,²⁰]icosa-1,9,12-triene-7,18-dione)

Structure for NP0160381 (16-hydroxy-9-isopropyl-2,5,13,16-tetramethyl-6,15,19-trioxatetracyclo[12.5.1.0⁵,¹⁰.0¹⁷,²⁰]icosa-1,9,12-triene-7,18-dione)

3D Structure for NP0160381 (16-hydroxy-9-isopropyl-2,5,13,16-tetramethyl-6,15,19-trioxatetracyclo[12.5.1.0⁵,¹⁰.0¹⁷,²⁰]icosa-1,9,12-triene-7,18-dione)