NP-MRD: Showing NP-Card for (+)-Hypopurin B (NP0079105)

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Record Information

Version

1.0

Created at

2022-04-29 00:10:03 UTC

Updated at

2022-04-29 00:10:03 UTC

NP-MRD ID

NP0079105

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(+)-Hypopurin B

Description

(1S,5S,6S,9S,11R,14R)-6-[2-(furan-3-yl)-2-oxoethyl]-1,7-dimethyl-10,12-dioxatetracyclo[7.4.1.0⁵,¹¹.0⁵,¹⁴]Tetradec-7-en-13-one belongs to the class of organic compounds known as aryl alkyl ketones. These are ketones have the generic structure RC(=O)R', where R = aryl group and R'=alkyl group. (+)-Hypopurin B is found in Hypoestes purpurea. Based on a literature review very few articles have been published on (1S,5S,6S,9S,11R,14R)-6-[2-(furan-3-yl)-2-oxoethyl]-1,7-dimethyl-10,12-dioxatetracyclo[7.4.1.0⁵,¹¹.0⁵,¹⁴]Tetradec-7-en-13-one.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652304292202102D          

 25 29  0  0  1  0            999 V2000
    1.7883    0.2142    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5913    1.2016    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7727    1.2533    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.2728    0.6413    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7421   -0.3767    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.3440   -0.6014    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7880   -0.5633    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.3272    0.0384    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9238    0.7682    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8462    0.6923    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.1951    0.4105    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1194   -0.3672    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.1316   -0.1161    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3625    0.7049    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1568    0.9280    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1469   -0.0546    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0567   -1.3433    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8666   -1.5006    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4077   -0.8778    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1353   -2.2806    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9243   -2.5216    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9389   -3.3465    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1589   -3.6152    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6622   -2.9564    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0148    1.5792    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  6  0  0  0
  5  6  1  1  0  0  0
  1  6  1  0  0  0  0
  5  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
  4 10  1  0  0  0  0
 10 11  1  1  0  0  0
 12 11  1  6  0  0  0
  5 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
  3 14  1  0  0  0  0
 14 15  2  0  0  0  0
  8 16  1  0  0  0  0
  7 17  1  6  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 18 20  1  0  0  0  0
 20 21  2  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  2  0  0  0  0
 20 24  1  0  0  0  0
  3 25  1  1  0  0  0
M  END


  Mrv1652304292202102D          

 25 29  0  0  1  0            999 V2000
    1.7883    0.2142    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5913    1.2016    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7727    1.2533    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.2728    0.6413    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7421   -0.3767    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.3440   -0.6014    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7880   -0.5633    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.3272    0.0384    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9238    0.7682    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8462    0.6923    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.1951    0.4105    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1194   -0.3672    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.1316   -0.1161    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3625    0.7049    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1568    0.9280    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1469   -0.0546    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0567   -1.3433    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8666   -1.5006    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4077   -0.8778    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1353   -2.2806    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9243   -2.5216    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9389   -3.3465    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1589   -3.6152    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6622   -2.9564    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0148    1.5792    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  6  0  0  0
  5  6  1  1  0  0  0
  1  6  1  0  0  0  0
  5  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
  4 10  1  0  0  0  0
 10 11  1  1  0  0  0
 12 11  1  6  0  0  0
  5 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
  3 14  1  0  0  0  0
 14 15  2  0  0  0  0
  8 16  1  0  0  0  0
  7 17  1  6  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 18 20  1  0  0  0  0
 20 21  2  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  2  0  0  0  0
 20 24  1  0  0  0  0
  3 25  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0079105

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1=C[C@@H]2O[C@@H]3OC(=O)[C@@]4(C)CCC[C@@]3([C@@H]24)[C@H]1CC(=O)C1=COC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C20H22O5/c1-11-8-15-16-19(2)5-3-6-20(16,18(24-15)25-17(19)22)13(11)9-14(21)12-4-7-23-10-12/h4,7-8,10,13,15-16,18H,3,5-6,9H2,1-2H3/t13-,15-,16-,18+,19-,20-/m0/s1

> <INCHI_KEY>
WRANWQZSRYWETI-VPFGTQIVSA-N

> <FORMULA>
C20H22O5

> <MOLECULAR_WEIGHT>
342.391

> <EXACT_MASS>
342.146723808

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
47

> <JCHEM_AVERAGE_POLARIZABILITY>
35.357023411087894

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1S,5S,6S,9S,11R,14R)-6-[2-(furan-3-yl)-2-oxoethyl]-1,7-dimethyl-10,12-dioxatetracyclo[7.4.1.0^{5,11}.0^{5,14}]tetradec-7-en-13-one

> <ALOGPS_LOGP>
2.78

> <JCHEM_LOGP>
2.961259987666666

> <ALOGPS_LOGS>
-3.68

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
15.351651099176479

> <JCHEM_PKA_STRONGEST_BASIC>
-3.0023176362063175

> <JCHEM_POLAR_SURFACE_AREA>
65.74000000000001

> <JCHEM_REFRACTIVITY>
89.1039

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
7.22e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1S,5S,6S,9S,11R,14R)-6-[2-(furan-3-yl)-2-oxoethyl]-1,7-dimethyl-10,12-dioxatetracyclo[7.4.1.0^{5,11}.0^{5,14}]tetradec-7-en-13-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 29-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   29-APR-22         0                                  
HETATM    1  C   UNK     0       3.338   0.400   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.970   2.243   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.442   2.340   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.509   1.197   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.385  -0.703   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.509  -1.123   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       3.338  -1.051   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.344   0.072   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       3.591   1.434   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.580   1.292   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      -0.364   0.766   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       0.223  -0.686   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       2.112  -0.217   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       2.543   1.316   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       4.026   1.732   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       5.874  -0.102   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       3.839  -2.507   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       5.351  -2.801   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       6.361  -1.639   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       5.853  -4.257   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       7.325  -4.707   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       7.353  -6.247   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       5.897  -6.748   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       4.970  -5.519   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       0.028   2.948   0.000  0.00  0.00           C+0
CONECT    1    2    6                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4   14   25                                             
CONECT    4    3    5   10                                                  
CONECT    5    4    6    7   12                                             
CONECT    6    5    1                                                       
CONECT    7    5    8   17                                                  
CONECT    8    7    9   16                                                  
CONECT    9    8   10                                                       
CONECT   10    9    4   11                                                  
CONECT   11   10   12                                                       
CONECT   12   11    5   13                                                  
CONECT   13   12   14                                                       
CONECT   14   13    3   15                                                  
CONECT   15   14                                                            
CONECT   16    8                                                            
CONECT   17    7   18                                                       
CONECT   18   17   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18   21   24                                                  
CONECT   21   20   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23   20                                                       
CONECT   25    3                                                            
MASTER        0    0    0    0    0    0    0    0   25    0   58    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₀H₂₂O₅

Average Mass

342.3910 Da

Monoisotopic Mass

342.14672 Da

IUPAC Name

(1S,5S,6S,9S,11R,14R)-6-[2-(furan-3-yl)-2-oxoethyl]-1,7-dimethyl-10,12-dioxatetracyclo[7.4.1.0^{5,11}.0^{5,14}]tetradec-7-en-13-one

Traditional Name

(1S,5S,6S,9S,11R,14R)-6-[2-(furan-3-yl)-2-oxoethyl]-1,7-dimethyl-10,12-dioxatetracyclo[7.4.1.0^{5,11}.0^{5,14}]tetradec-7-en-13-one

CAS Registry Number

Not Available

SMILES

CC1=C[C@@H]2O[C@@H]3OC(=O)[C@@]4(C)CCC[C@@]3([C@@H]24)[C@H]1CC(=O)C1=COC=C1

InChI Identifier

InChI=1S/C20H22O5/c1-11-8-15-16-19(2)5-3-6-20(16,18(24-15)25-17(19)22)13(11)9-14(21)12-4-7-23-10-12/h4,7-8,10,13,15-16,18H,3,5-6,9H2,1-2H3/t13-,15-,16-,18+,19-,20-/m0/s1

InChI Key

WRANWQZSRYWETI-VPFGTQIVSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Hypoestes purpurea	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as aryl alkyl ketones. These are ketones have the generic structure RC(=O)R', where R = aryl group and R'=alkyl group.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbonyl compounds

Direct Parent

Aryl alkyl ketones

Alternative Parents

Substituents

Aryl alkyl ketone
Delta_valerolactone
Dioxepane
Delta valerolactone
1,3-dioxepane
Oxane
Heteroaromatic compound
Tetrahydrofuran
Furan
Lactone
Carboxylic acid ester
Oxacycle
Organoheterocyclic compound
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Acetal
Organic oxide
Hydrocarbon derivative
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	2.78	ALOGPS
logP	2.96	ChemAxon
logS	-3.7	ALOGPS
pKa (Strongest Acidic)	15.35	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	65.74 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	89.1 m³·mol⁻¹	ChemAxon
Polarizability	35.36 Å³	ChemAxon
Number of Rings	5	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

162924356

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for (+)-Hypopurin B (NP0079105)

MOL for NP0079105 ((+)-Hypopurin B)

3D MOL for NP0079105 ((+)-Hypopurin B)

3D SDF for NP0079105 ((+)-Hypopurin B)

3D-SDF for NP0079105 ((+)-Hypopurin B)

PDB for NP0079105 ((+)-Hypopurin B)

3D PDB for NP0079105 ((+)-Hypopurin B)

SMILES for NP0079105 ((+)-Hypopurin B)

INCHI for NP0079105 ((+)-Hypopurin B)

Structure for NP0079105 ((+)-Hypopurin B)

3D Structure for NP0079105 ((+)-Hypopurin B)