NP-MRD: Showing NP-Card for Jatropholone B (NP0081617)

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Record Information

Version

2.0

Created at

2022-04-29 02:37:41 UTC

Updated at

2022-04-29 02:37:41 UTC

NP-MRD ID

NP0081617

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Jatropholone B

Description

(4S,10S,12S)-7-hydroxy-4,8,11,11-tetramethyl-15-methylidenetetracyclo[7.6.0.0²,⁶.0¹⁰,¹²]Pentadeca-1(9),2(6),7-trien-3-one belongs to the class of organic compounds known as indanones. Indanones are compounds containing an indane ring bearing a ketone group. Jatropholone B is found in Jatropha gossypifolia and Jatropha integerrima. Based on a literature review very few articles have been published on (4S,10S,12S)-7-hydroxy-4,8,11,11-tetramethyl-15-methylidenetetracyclo[7.6.0.0²,⁶.0¹⁰,¹²]Pentadeca-1(9),2(6),7-trien-3-one.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652304292204372D          

 22 25  0  0  1  0            999 V2000
    5.6736    1.9582    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4346    1.6395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6600    0.8459    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.1800    0.1749    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.3561    0.1318    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8088    0.7491    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9501    1.5619    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2791    2.0418    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0005    0.5836    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7396   -0.1990    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2870   -0.8163    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0953   -0.6509    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6426   -1.2681    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0261   -1.5989    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9147   -0.1928    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6657    0.5938    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.3368    1.0736    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3430    1.8986    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8830    0.8546    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0011    0.0947    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2754   -0.6833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8261    0.0864    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  3  2  1  6  0  0  0
  3  4  1  0  0  0  0
  4  5  1  1  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  1  7  1  0  0  0  0
  7  8  2  0  0  0  0
  6  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
  5 12  1  0  0  0  0
 12 13  1  0  0  0  0
 11 14  1  0  0  0  0
 10 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
  9 17  1  0  0  0  0
 17 18  2  0  0  0  0
 16 19  1  6  0  0  0
  4 20  1  0  0  0  0
  3 20  1  0  0  0  0
 20 21  1  0  0  0  0
 20 22  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0081617

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@H]1CC2=C(C1=O)C1=C([C@H]3[C@H](CCC1=C)C3(C)C)C(C)=C2O

> <INCHI_IDENTIFIER>
InChI=1S/C20H24O2/c1-9-6-7-13-17(20(13,4)5)15-11(3)19(22)12-8-10(2)18(21)16(12)14(9)15/h10,13,17,22H,1,6-8H2,2-5H3/t10-,13-,17+/m0/s1

> <INCHI_KEY>
BMHPRIPRPDSKRK-SIMVJXQJSA-N

> <FORMULA>
C20H24O2

> <MOLECULAR_WEIGHT>
296.41

> <EXACT_MASS>
296.177630013

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
46

> <JCHEM_AVERAGE_POLARIZABILITY>
34.526208135622184

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(4S,10S,12S)-7-hydroxy-4,8,11,11-tetramethyl-15-methylidenetetracyclo[7.6.0.0^{2,6}.0^{10,12}]pentadeca-1(9),2(6),7-trien-3-one

> <ALOGPS_LOGP>
4.16

> <JCHEM_LOGP>
4.817137680333333

> <ALOGPS_LOGS>
-4.79

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
17.180677897705227

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.30439343190619

> <JCHEM_PKA_STRONGEST_BASIC>
-6.0129640892914304

> <JCHEM_POLAR_SURFACE_AREA>
37.3

> <JCHEM_REFRACTIVITY>
89.4493

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.80e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(4S,10S,12S)-7-hydroxy-4,8,11,11-tetramethyl-15-methylidenetetracyclo[7.6.0.0^{2,6}.0^{10,12}]pentadeca-1(9),2(6),7-trien-3-one

> <JCHEM_VEBER_RULE>
1

$$$$

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      10.591   3.655   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      12.011   3.060   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      12.432   1.579   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      11.536   0.326   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       9.998   0.246   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       8.976   1.398   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       9.240   2.915   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       7.988   3.811   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       7.468   1.089   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       6.981  -0.372   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       8.002  -1.524   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       9.511  -1.215   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      10.533  -2.367   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       7.515  -2.985   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       5.441  -0.360   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       4.976   1.108   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       6.229   2.004   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       6.240   3.544   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       3.515   1.595   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      13.069   0.177   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      13.581  -1.276   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      14.609   0.161   0.000  0.00  0.00           C+0
CONECT    1    2    7                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4   20                                                  
CONECT    4    3    5   20                                                  
CONECT    5    4    6   12                                                  
CONECT    6    5    7    9                                                  
CONECT    7    6    1    8                                                  
CONECT    8    7                                                            
CONECT    9    6   10   17                                                  
CONECT   10    9   11   15                                                  
CONECT   11   10   12   14                                                  
CONECT   12   11    5   13                                                  
CONECT   13   12                                                            
CONECT   14   11                                                            
CONECT   15   10   16                                                       
CONECT   16   15   17   19                                                  
CONECT   17   16    9   18                                                  
CONECT   18   17                                                            
CONECT   19   16                                                            
CONECT   20    4    3   21   22                                             
CONECT   21   20                                                            
CONECT   22   20                                                            
MASTER        0    0    0    0    0    0    0    0   22    0   50    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₀H₂₄O₂

Average Mass

296.4100 Da

Monoisotopic Mass

296.17763 Da

IUPAC Name

(4S,10S,12S)-7-hydroxy-4,8,11,11-tetramethyl-15-methylidenetetracyclo[7.6.0.0^{2,6}.0^{10,12}]pentadeca-1(9),2(6),7-trien-3-one

Traditional Name

(4S,10S,12S)-7-hydroxy-4,8,11,11-tetramethyl-15-methylidenetetracyclo[7.6.0.0^{2,6}.0^{10,12}]pentadeca-1(9),2(6),7-trien-3-one

CAS Registry Number

Not Available

SMILES

C[C@H]1CC2=C(C1=O)C1=C([C@H]3[C@H](CCC1=C)C3(C)C)C(C)=C2O

InChI Identifier

InChI=1S/C20H24O2/c1-9-6-7-13-17(20(13,4)5)15-11(3)19(22)12-8-10(2)18(21)16(12)14(9)15/h10,13,17,22H,1,6-8H2,2-5H3/t10-,13-,17+/m0/s1

InChI Key

BMHPRIPRPDSKRK-SIMVJXQJSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Jatropha gossypifolia	Plant	KNApSAcK
Jatropha integerrima	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as indanones. Indanones are compounds containing an indane ring bearing a ketone group.

Kingdom

Super Class

Class

Sub Class

Direct Parent

Alternative Parents

Substituents

Indanone
Aryl alkyl ketone
Aryl ketone
Ketone
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen 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	4.16	ALOGPS
logP	4.82	ChemAxon
logS	-4.8	ALOGPS
pKa (Strongest Acidic)	9.3	ChemAxon
pKa (Strongest Basic)	-6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	37.3 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	89.45 m³·mol⁻¹	ChemAxon
Polarizability	34.53 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	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

162949975

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Jatropholone B (NP0081617)

MOL for NP0081617 (Jatropholone B)

3D MOL for NP0081617 (Jatropholone B)

3D SDF for NP0081617 (Jatropholone B)

3D-SDF for NP0081617 (Jatropholone B)

PDB for NP0081617 (Jatropholone B)

3D PDB for NP0081617 (Jatropholone B)

SMILES for NP0081617 (Jatropholone B)

INCHI for NP0081617 (Jatropholone B)

Structure for NP0081617 (Jatropholone B)

3D Structure for NP0081617 (Jatropholone B)