NP-MRD: Showing NP-Card for 13-(furan-2-yl)-15-isopropyl-4,6,6,12-tetramethyl-8,14,19,20-tetraoxahexacyclo[13.3.1.1³,¹⁸.0²,⁷.0⁹,¹⁸.0¹²,¹⁷]icos-4-ene-2,3,9-triol (NP0246917)

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Record Information

Version

2.0

Created at

2022-09-07 08:32:22 UTC

Updated at

2022-09-07 08:32:23 UTC

NP-MRD ID

NP0246917

Secondary Accession Numbers

None

Natural Product Identification

Common Name

13-(furan-2-yl)-15-isopropyl-4,6,6,12-tetramethyl-8,14,19,20-tetraoxahexacyclo[13.3.1.1³,¹⁸.0²,⁷.0⁹,¹⁸.0¹²,¹⁷]icos-4-ene-2,3,9-triol

Description

13-(Furan-2-yl)-4,6,6,12-tetramethyl-15-(propan-2-yl)-8,14,19,20-tetraoxahexacyclo[13.3.1.1³,¹⁸.0²,⁷.0⁹,¹⁸.0¹²,¹⁷]Icos-4-ene-2,3,9-triol belongs to the class of organic compounds known as furopyrans. These are organic polycyclic compounds containing a furan ring fused to a pyran ring. Furan is a five-membered aromatic ring with four carbon atoms and one oxygen atom. Pyran a six-membered heterocyclic, non-aromatic ring, made up of five carbon atoms and one oxygen atom and containing two double bonds. 13-(furan-2-yl)-15-isopropyl-4,6,6,12-tetramethyl-8,14,19,20-tetraoxahexacyclo[13.3.1.1³,¹⁸.0²,⁷.0⁹,¹⁸.0¹²,¹⁷]icos-4-ene-2,3,9-triol is found in Entandrophragma utile. 13-(Furan-2-yl)-4,6,6,12-tetramethyl-15-(propan-2-yl)-8,14,19,20-tetraoxahexacyclo[13.3.1.1³,¹⁸.0²,⁷.0⁹,¹⁸.0¹²,¹⁷]Icos-4-ene-2,3,9-triol is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv0541 04121514312D          

 35 41  0  0  0  0            999 V2000
    4.3774    3.3645    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    3.4777    0.5532    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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M  END

     RDKit          3D

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M  END


  Mrv0541 04121514312D          

 35 41  0  0  0  0            999 V2000
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  7  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
 11 13  1  0  0  0  0
 13 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
 15 18  1  0  0  0  0
 18 19  2  0  0  0  0
 19 20  1  0  0  0  0
 19 21  1  0  0  0  0
 21 22  1  0  0  0  0
 21 23  1  0  0  0  0
 23 24  1  0  0  0  0
  6 24  1  0  0  0  0
 11 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
  4 26  1  0  0  0  0
 25 27  1  0  0  0  0
 14 27  1  0  0  0  0
 21 27  1  0  0  0  0
 27 28  1  0  0  0  0
  7 29  1  0  0  0  0
 29 30  1  0  0  0  0
  4 30  1  0  0  0  0
 29 31  1  0  0  0  0
 31 32  1  0  0  0  0
 32 33  1  0  0  0  0
 33 34  2  0  0  0  0
 34 35  1  0  0  0  0
 31 35  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0246917

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)C12CC3C45OC6(O)C(C)=CC(C)(C)C(OC4(O)CCC3(C)C(O1)C1=CC=CO1)C6(O)C5O2

> <INCHI_IDENTIFIER>
InChI=1S/C27H36O8/c1-14(2)23-13-17-22(6,18(32-23)16-8-7-11-31-16)9-10-24(28)26(17)20(33-23)25(29)19(34-24)21(4,5)12-15(3)27(25,30)35-26/h7-8,11-12,14,17-20,28-30H,9-10,13H2,1-6H3

> <INCHI_KEY>
RQPCTKKIUSBBLR-UHFFFAOYSA-N

> <FORMULA>
C27H36O8

> <MOLECULAR_WEIGHT>
488.577

> <EXACT_MASS>
488.241018119

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
71

> <JCHEM_AVERAGE_POLARIZABILITY>
51.82747090013948

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
13-(furan-2-yl)-4,6,6,12-tetramethyl-15-(propan-2-yl)-8,14,19,20-tetraoxahexacyclo[13.3.1.1³,¹⁸.0²,⁷.0⁹,¹⁸.0¹²,¹⁷]icos-4-ene-2,3,9-triol

> <ALOGPS_LOGP>
2.49

> <JCHEM_LOGP>
3.4963979093333326

> <ALOGPS_LOGS>
-3.22

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
7

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
10.926789495670153

> <JCHEM_PKA_STRONGEST_ACIDIC>
10.130668378428636

> <JCHEM_PKA_STRONGEST_BASIC>
-2.8780969896689386

> <JCHEM_POLAR_SURFACE_AREA>
110.75000000000001

> <JCHEM_REFRACTIVITY>
123.04780000000004

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.96e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
13-(furan-2-yl)-15-isopropyl-4,6,6,12-tetramethyl-8,14,19,20-tetraoxahexacyclo[13.3.1.1³,¹⁸.0²,⁷.0⁹,¹⁸.0¹²,¹⁷]icos-4-ene-2,3,9-triol

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 12-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   12-APR-15         0                                  
HETATM    1  C   UNK     0       8.171   6.280   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       6.666   5.957   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       5.632   7.099   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       6.193   4.491   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       5.842   3.408   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       5.345   1.971   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.492   1.033   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       7.697   0.075   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.849  -0.462   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.327  -0.786   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       3.430   0.503   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       2.874  -0.933   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0       1.920   0.159   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       0.975   1.348   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -0.581   1.469   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -0.455  -0.065   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -2.076   1.101   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -1.188   2.899   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -0.215   4.154   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -0.838   5.563   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       1.422   4.025   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       1.436   5.565   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0       3.077   4.125   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0       3.831   2.170   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       3.502   3.260   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0       4.531   4.690   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0       1.791   2.672   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0       2.753   1.470   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0       7.805   1.998   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0       7.684   3.668   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0       9.203   1.353   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0      10.547   2.105   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0      11.678   1.059   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      11.032  -0.340   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       9.503  -0.158   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5   26   30                                             
CONECT    5    4    6                                                       
CONECT    6    5    7   24                                                  
CONECT    7    6    8    9   29                                             
CONECT    8    7                                                            
CONECT    9    7   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12   13   24                                             
CONECT   12   11                                                            
CONECT   13   11   14                                                       
CONECT   14   13   15   27                                                  
CONECT   15   14   16   17   18                                             
CONECT   16   15                                                            
CONECT   17   15                                                            
CONECT   18   15   19                                                       
CONECT   19   18   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19   22   23   27                                             
CONECT   22   21                                                            
CONECT   23   21   24                                                       
CONECT   24   23    6   11   25                                             
CONECT   25   24   26   27                                                  
CONECT   26   25    4                                                       
CONECT   27   25   14   21   28                                             
CONECT   28   27                                                            
CONECT   29    7   30   31                                                  
CONECT   30   29    4                                                       
CONECT   31   29   32   35                                                  
CONECT   32   31   33                                                       
CONECT   33   32   34                                                       
CONECT   34   33   35                                                       
CONECT   35   34   31                                                       
MASTER        0    0    0    0    0    0    0    0   35    0   82    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₇H₃₆O₈

Average Mass

488.5770 Da

Monoisotopic Mass

488.24102 Da

IUPAC Name

13-(furan-2-yl)-4,6,6,12-tetramethyl-15-(propan-2-yl)-8,14,19,20-tetraoxahexacyclo[13.3.1.1³,¹⁸.0²,⁷.0⁹,¹⁸.0¹²,¹⁷]icos-4-ene-2,3,9-triol

Traditional Name

13-(furan-2-yl)-15-isopropyl-4,6,6,12-tetramethyl-8,14,19,20-tetraoxahexacyclo[13.3.1.1³,¹⁸.0²,⁷.0⁹,¹⁸.0¹²,¹⁷]icos-4-ene-2,3,9-triol

CAS Registry Number

Not Available

SMILES

CC(C)C12CC3C45OC6(O)C(C)=CC(C)(C)C(OC4(O)CCC3(C)C(O1)C1=CC=CO1)C6(O)C5O2

InChI Identifier

InChI=1S/C27H36O8/c1-14(2)23-13-17-22(6,18(32-23)16-8-7-11-31-16)9-10-24(28)26(17)20(33-23)25(29)19(34-24)21(4,5)12-15(3)27(25,30)35-26/h7-8,11-12,14,17-20,28-30H,9-10,13H2,1-6H3

InChI Key

RQPCTKKIUSBBLR-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Entandrophragma utile	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as furopyrans. These are organic polycyclic compounds containing a furan ring fused to a pyran ring. Furan is a five-membered aromatic ring with four carbon atoms and one oxygen atom. Pyran a six-membered heterocyclic, non-aromatic ring, made up of five carbon atoms and one oxygen atom and containing two double bonds.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Furopyrans

Sub Class

Not Available

Direct Parent

Furopyrans

Alternative Parents

Substituents

Furopyran
1,4-dioxepane
Ketal
Dioxepane
Monosaccharide
Oxane
Pyran
Cyclic alcohol
Furan
Heteroaromatic compound
Tetrahydrofuran
Tertiary alcohol
Hemiacetal
Acetal
Oxacycle
Polyol
Alcohol
Hydrocarbon derivative
Organooxygen compound
Organic oxygen compound
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	2.49	ALOGPS
logP	3.5	ChemAxon
logS	-3.2	ALOGPS
pKa (Strongest Acidic)	10.13	ChemAxon
pKa (Strongest Basic)	-2.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	110.75 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	123.05 m³·mol⁻¹	ChemAxon
Polarizability	51.83 Å³	ChemAxon
Number of Rings	7	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	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 13-(furan-2-yl)-15-isopropyl-4,6,6,12-tetramethyl-8,14,19,20-tetraoxahexacyclo[13.3.1.1³,¹⁸.0²,⁷.0⁹,¹⁸.0¹²,¹⁷]icos-4-ene-2,3,9-triol (NP0246917)

MOL for NP0246917 (13-(furan-2-yl)-15-isopropyl-4,6,6,12-tetramethyl-8,14,19,20-tetraoxahexacyclo[13.3.1.1³,¹⁸.0²,⁷.0⁹,¹⁸.0¹²,¹⁷]icos-4-ene-2,3,9-triol)

3D MOL for NP0246917 (13-(furan-2-yl)-15-isopropyl-4,6,6,12-tetramethyl-8,14,19,20-tetraoxahexacyclo[13.3.1.1³,¹⁸.0²,⁷.0⁹,¹⁸.0¹²,¹⁷]icos-4-ene-2,3,9-triol)

3D SDF for NP0246917 (13-(furan-2-yl)-15-isopropyl-4,6,6,12-tetramethyl-8,14,19,20-tetraoxahexacyclo[13.3.1.1³,¹⁸.0²,⁷.0⁹,¹⁸.0¹²,¹⁷]icos-4-ene-2,3,9-triol)

3D-SDF for NP0246917 (13-(furan-2-yl)-15-isopropyl-4,6,6,12-tetramethyl-8,14,19,20-tetraoxahexacyclo[13.3.1.1³,¹⁸.0²,⁷.0⁹,¹⁸.0¹²,¹⁷]icos-4-ene-2,3,9-triol)

PDB for NP0246917 (13-(furan-2-yl)-15-isopropyl-4,6,6,12-tetramethyl-8,14,19,20-tetraoxahexacyclo[13.3.1.1³,¹⁸.0²,⁷.0⁹,¹⁸.0¹²,¹⁷]icos-4-ene-2,3,9-triol)

3D PDB for NP0246917 (13-(furan-2-yl)-15-isopropyl-4,6,6,12-tetramethyl-8,14,19,20-tetraoxahexacyclo[13.3.1.1³,¹⁸.0²,⁷.0⁹,¹⁸.0¹²,¹⁷]icos-4-ene-2,3,9-triol)

SMILES for NP0246917 (13-(furan-2-yl)-15-isopropyl-4,6,6,12-tetramethyl-8,14,19,20-tetraoxahexacyclo[13.3.1.1³,¹⁸.0²,⁷.0⁹,¹⁸.0¹²,¹⁷]icos-4-ene-2,3,9-triol)

INCHI for NP0246917 (13-(furan-2-yl)-15-isopropyl-4,6,6,12-tetramethyl-8,14,19,20-tetraoxahexacyclo[13.3.1.1³,¹⁸.0²,⁷.0⁹,¹⁸.0¹²,¹⁷]icos-4-ene-2,3,9-triol)

Structure for NP0246917 (13-(furan-2-yl)-15-isopropyl-4,6,6,12-tetramethyl-8,14,19,20-tetraoxahexacyclo[13.3.1.1³,¹⁸.0²,⁷.0⁹,¹⁸.0¹²,¹⁷]icos-4-ene-2,3,9-triol)

3D Structure for NP0246917 (13-(furan-2-yl)-15-isopropyl-4,6,6,12-tetramethyl-8,14,19,20-tetraoxahexacyclo[13.3.1.1³,¹⁸.0²,⁷.0⁹,¹⁸.0¹²,¹⁷]icos-4-ene-2,3,9-triol)