NP-MRD: Showing NP-Card for 1-[(4r,11s)-7-hydroxy-4,11-bis(2-hydroxypropan-2-yl)-3,10-dioxatricyclo[7.3.0.0²,⁶]dodeca-1(9),2(6),7-trien-8-yl]-2-methylpropan-1-one (NP0224044)

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Record Information

Version

2.0

Created at

2022-09-06 02:18:10 UTC

Updated at

2022-09-06 02:18:10 UTC

NP-MRD ID

NP0224044

Secondary Accession Numbers

None

Natural Product Identification

Common Name

1-[(4r,11s)-7-hydroxy-4,11-bis(2-hydroxypropan-2-yl)-3,10-dioxatricyclo[7.3.0.0²,⁶]dodeca-1(9),2(6),7-trien-8-yl]-2-methylpropan-1-one

Description

1-[(4R,11S)-7-hydroxy-4,11-bis(2-hydroxypropan-2-yl)-3,10-dioxatricyclo[7.3.0.0²,⁶]Dodeca-1,6,8-trien-8-yl]-2-methylpropan-1-one belongs to the class of organic compounds known as coumarans. Coumarans are compounds containing the coumaran skeleton, which consists of a benzene ring fused to a 2,3-dihydrofuran ring. 1-[(4r,11s)-7-hydroxy-4,11-bis(2-hydroxypropan-2-yl)-3,10-dioxatricyclo[7.3.0.0²,⁶]dodeca-1(9),2(6),7-trien-8-yl]-2-methylpropan-1-one is found in Garcinia subelliptica. Based on a literature review very few articles have been published on 1-[(4R,11S)-7-hydroxy-4,11-bis(2-hydroxypropan-2-yl)-3,10-dioxatricyclo[7.3.0.0²,⁶]Dodeca-1,6,8-trien-8-yl]-2-methylpropan-1-one.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652309062204182D          

 26 28  0  0  1  0            999 V2000
    1.0446    3.1970    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4571    2.4826    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0446    1.7681    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2821    2.4826    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6946    3.1970    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6946    1.7681    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5196    1.7681    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9321    2.4826    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9321    1.0536    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5196    0.3391    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6946    0.3391    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2821    1.0536    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4752    0.8821    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3889    0.0616    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.6745   -0.3509    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0400   -0.7634    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0870   -1.0654    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2620    0.3636    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1426   -0.2740    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0717   -0.2740    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8253    0.0616    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.5398   -0.3509    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2543   -0.7634    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1273   -1.0654    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9523    0.3636    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7391    0.8821    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
  2  4  1  0  0  0  0
  4  5  2  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
  7  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
  6 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  1  0  0  0
 15 16  1  0  0  0  0
 15 17  1  0  0  0  0
 15 18  1  0  0  0  0
 14 19  1  0  0  0  0
 11 19  1  0  0  0  0
 10 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  6  0  0  0
 22 23  1  0  0  0  0
 22 24  1  0  0  0  0
 22 25  1  0  0  0  0
 21 26  1  0  0  0  0
  9 26  1  0  0  0  0
M  END


  Mrv1652309062204182D          

 26 28  0  0  1  0            999 V2000
    1.0446    3.1970    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4571    2.4826    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0446    1.7681    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2821    2.4826    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6946    3.1970    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6946    1.7681    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5196    1.7681    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9321    2.4826    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9321    1.0536    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5196    0.3391    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6946    0.3391    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2821    1.0536    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4752    0.8821    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3889    0.0616    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.6745   -0.3509    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0400   -0.7634    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0870   -1.0654    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2620    0.3636    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1426   -0.2740    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0717   -0.2740    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8253    0.0616    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.5398   -0.3509    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2543   -0.7634    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1273   -1.0654    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9523    0.3636    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7391    0.8821    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
  2  4  1  0  0  0  0
  4  5  2  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
  7  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
  6 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  1  0  0  0
 15 16  1  0  0  0  0
 15 17  1  0  0  0  0
 15 18  1  0  0  0  0
 14 19  1  0  0  0  0
 11 19  1  0  0  0  0
 10 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  6  0  0  0
 22 23  1  0  0  0  0
 22 24  1  0  0  0  0
 22 25  1  0  0  0  0
 21 26  1  0  0  0  0
  9 26  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0224044

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)C(=O)C1=C(O)C2=C(O[C@H](C2)C(C)(C)O)C2=C1O[C@@H](C2)C(C)(C)O

> <INCHI_IDENTIFIER>
InChI=1S/C20H28O6/c1-9(2)15(21)14-16(22)10-7-12(19(3,4)23)25-17(10)11-8-13(20(5,6)24)26-18(11)14/h9,12-13,22-24H,7-8H2,1-6H3/t12-,13+/m1/s1

> <INCHI_KEY>
VPBDCGLRLMBBMF-OLZOCXBDSA-N

> <FORMULA>
C20H28O6

> <MOLECULAR_WEIGHT>
364.438

> <EXACT_MASS>
364.188588622

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
54

> <JCHEM_AVERAGE_POLARIZABILITY>
40.24458303865718

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
1-[(4R,11S)-7-hydroxy-4,11-bis(2-hydroxypropan-2-yl)-3,10-dioxatricyclo[7.3.0.0^{2,6}]dodeca-1(9),2(6),7-trien-8-yl]-2-methylpropan-1-one

> <JCHEM_LOGP>
3.018918121666667

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.995483338798977

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.5753656988201

> <JCHEM_PKA_STRONGEST_BASIC>
-3.1064455912304307

> <JCHEM_POLAR_SURFACE_AREA>
96.22000000000001

> <JCHEM_REFRACTIVITY>
97.22770000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
1-[(4R,11S)-7-hydroxy-4,11-bis(2-hydroxypropan-2-yl)-3,10-dioxatricyclo[7.3.0.0^{2,6}]dodeca-1(9),2(6),7-trien-8-yl]-2-methylpropan-1-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 06-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-SEP-22         0                                  
HETATM    1  C   UNK     0       1.950   5.968   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.720   4.634   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.950   3.300   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       4.260   4.634   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0       5.030   5.968   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       5.030   3.300   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.570   3.300   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       7.340   4.634   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       7.340   1.967   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       6.570   0.633   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.030   0.633   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.260   1.967   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       2.754   1.647   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       2.593   0.115   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       1.259  -0.655   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -0.075  -1.425   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       2.029  -1.989   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       0.489   0.679   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       4.000  -0.511   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       7.600  -0.511   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       9.007   0.115   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      10.341  -0.655   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      11.675  -1.425   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       9.571  -1.989   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0      11.111   0.679   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0       8.846   1.647   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7   12                                                  
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10   26                                                  
CONECT   10    9   11   20                                                  
CONECT   11   10   12   19                                                  
CONECT   12   11    6   13                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15   19                                                  
CONECT   15   14   16   17   18                                             
CONECT   16   15                                                            
CONECT   17   15                                                            
CONECT   18   15                                                            
CONECT   19   14   11                                                       
CONECT   20   10   21                                                       
CONECT   21   20   22   26                                                  
CONECT   22   21   23   24   25                                             
CONECT   23   22                                                            
CONECT   24   22                                                            
CONECT   25   22                                                            
CONECT   26   21    9                                                       
MASTER        0    0    0    0    0    0    0    0   26    0   56    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₀H₂₈O₆

Average Mass

364.4380 Da

Monoisotopic Mass

364.18859 Da

IUPAC Name

1-[(4R,11S)-7-hydroxy-4,11-bis(2-hydroxypropan-2-yl)-3,10-dioxatricyclo[7.3.0.0^{2,6}]dodeca-1(9),2(6),7-trien-8-yl]-2-methylpropan-1-one

Traditional Name

1-[(4R,11S)-7-hydroxy-4,11-bis(2-hydroxypropan-2-yl)-3,10-dioxatricyclo[7.3.0.0^{2,6}]dodeca-1(9),2(6),7-trien-8-yl]-2-methylpropan-1-one

CAS Registry Number

Not Available

SMILES

CC(C)C(=O)C1=C(O)C2=C(O[C@H](C2)C(C)(C)O)C2=C1O[C@@H](C2)C(C)(C)O

InChI Identifier

InChI=1S/C20H28O6/c1-9(2)15(21)14-16(22)10-7-12(19(3,4)23)25-17(10)11-8-13(20(5,6)24)26-18(11)14/h9,12-13,22-24H,7-8H2,1-6H3/t12-,13+/m1/s1

InChI Key

VPBDCGLRLMBBMF-OLZOCXBDSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Garcinia subelliptica	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as coumarans. Coumarans are compounds containing the coumaran skeleton, which consists of a benzene ring fused to a 2,3-dihydrofuran ring.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Coumarans

Sub Class

Not Available

Direct Parent

Coumarans

Alternative Parents

Substituents

Coumaran
Aryl alkyl ketone
Aryl ketone
Alkyl aryl ether
Benzenoid
Tertiary alcohol
Vinylogous acid
Ketone
Ether
Oxacycle
Organooxygen compound
Organic oxide
Alcohol
Organic oxygen compound
Hydrocarbon derivative
Aldehyde
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	3.02	ChemAxon
pKa (Strongest Acidic)	9.58	ChemAxon
pKa (Strongest Basic)	-3.1	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	96.22 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	97.23 m³·mol⁻¹	ChemAxon
Polarizability	40.24 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

24774694

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 1-[(4r,11s)-7-hydroxy-4,11-bis(2-hydroxypropan-2-yl)-3,10-dioxatricyclo[7.3.0.0²,⁶]dodeca-1(9),2(6),7-trien-8-yl]-2-methylpropan-1-one (NP0224044)

MOL for NP0224044 (1-[(4r,11s)-7-hydroxy-4,11-bis(2-hydroxypropan-2-yl)-3,10-dioxatricyclo[7.3.0.0²,⁶]dodeca-1(9),2(6),7-trien-8-yl]-2-methylpropan-1-one)

3D MOL for NP0224044 (1-[(4r,11s)-7-hydroxy-4,11-bis(2-hydroxypropan-2-yl)-3,10-dioxatricyclo[7.3.0.0²,⁶]dodeca-1(9),2(6),7-trien-8-yl]-2-methylpropan-1-one)

3D SDF for NP0224044 (1-[(4r,11s)-7-hydroxy-4,11-bis(2-hydroxypropan-2-yl)-3,10-dioxatricyclo[7.3.0.0²,⁶]dodeca-1(9),2(6),7-trien-8-yl]-2-methylpropan-1-one)

3D-SDF for NP0224044 (1-[(4r,11s)-7-hydroxy-4,11-bis(2-hydroxypropan-2-yl)-3,10-dioxatricyclo[7.3.0.0²,⁶]dodeca-1(9),2(6),7-trien-8-yl]-2-methylpropan-1-one)

PDB for NP0224044 (1-[(4r,11s)-7-hydroxy-4,11-bis(2-hydroxypropan-2-yl)-3,10-dioxatricyclo[7.3.0.0²,⁶]dodeca-1(9),2(6),7-trien-8-yl]-2-methylpropan-1-one)

3D PDB for NP0224044 (1-[(4r,11s)-7-hydroxy-4,11-bis(2-hydroxypropan-2-yl)-3,10-dioxatricyclo[7.3.0.0²,⁶]dodeca-1(9),2(6),7-trien-8-yl]-2-methylpropan-1-one)

SMILES for NP0224044 (1-[(4r,11s)-7-hydroxy-4,11-bis(2-hydroxypropan-2-yl)-3,10-dioxatricyclo[7.3.0.0²,⁶]dodeca-1(9),2(6),7-trien-8-yl]-2-methylpropan-1-one)

INCHI for NP0224044 (1-[(4r,11s)-7-hydroxy-4,11-bis(2-hydroxypropan-2-yl)-3,10-dioxatricyclo[7.3.0.0²,⁶]dodeca-1(9),2(6),7-trien-8-yl]-2-methylpropan-1-one)

Structure for NP0224044 (1-[(4r,11s)-7-hydroxy-4,11-bis(2-hydroxypropan-2-yl)-3,10-dioxatricyclo[7.3.0.0²,⁶]dodeca-1(9),2(6),7-trien-8-yl]-2-methylpropan-1-one)

3D Structure for NP0224044 (1-[(4r,11s)-7-hydroxy-4,11-bis(2-hydroxypropan-2-yl)-3,10-dioxatricyclo[7.3.0.0²,⁶]dodeca-1(9),2(6),7-trien-8-yl]-2-methylpropan-1-one)