NP-MRD: Showing NP-Card for Sterekunthal B (NP0075791)

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Record Information

Version

2.0

Created at

2022-04-28 21:01:46 UTC

Updated at

2022-04-28 21:01:46 UTC

NP-MRD ID

NP0075791

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Sterekunthal B

Description

(1S,12R,13S,16R,18R)-16,18-dimethyl-2,9-dioxo-17-oxapentacyclo[11.4.1.0¹,¹⁰.0³,⁸.0¹²,¹⁶]Octadeca-3,5,7,10-tetraene-18-carbaldehyde belongs to the class of organic compounds known as anthraquinones. These are organic compounds containing either anthracene-9,10-quinone, 1,4-anthraquinone, or 1,2-anthraquinone. Sterekunthal B is found in Stereospermum colais, Stereospermum kunthianum , Stereospermum personatum and Sterospermum kunthianum . Based on a literature review very few articles have been published on (1S,12R,13S,16R,18R)-16,18-dimethyl-2,9-dioxo-17-oxapentacyclo[11.4.1.0¹,¹⁰.0³,⁸.0¹²,¹⁶]Octadeca-3,5,7,10-tetraene-18-carbaldehyde.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652304282223012D          

 24 28  0  0  1  0            999 V2000
    7.7869    0.0240    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9432    0.8341    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3198    1.3745    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5402    1.1048    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3839    0.2948    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0072   -0.2456    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5630    0.0694    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4806   -0.7514    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7941    0.4581    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.0680    1.2914    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3762    1.7872    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6968    1.2615    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.5033    0.3076    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.2204   -0.1813    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.8887   -0.9367    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3770   -1.6016    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7228   -0.8357    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7768   -0.1457    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2751    0.5253    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0449    0.8734    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.9714    0.7081    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6633    1.6048    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8600    1.5991    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9661    2.4172    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  1  6  1  0  0  0  0
  5  7  1  0  0  0  0
  7  8  2  0  0  0  0
  7  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 12 11  1  6  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
  9 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 14 17  1  1  0  0  0
 13 18  1  1  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 12 20  1  0  0  0  0
 20 21  1  0  0  0  0
  9 21  1  1  0  0  0
 20 22  1  1  0  0  0
 10 23  1  0  0  0  0
  4 23  1  0  0  0  0
 23 24  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0075791

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@@]12CC[C@H]3[C@H]1C=C1C(=O)C4=CC=CC=C4C(=O)[C@]1(O2)[C@]3(C)C=O

> <INCHI_IDENTIFIER>
InChI=1S/C20H18O4/c1-18(10-21)13-7-8-19(2)14(13)9-15-16(22)11-5-3-4-6-12(11)17(23)20(15,18)24-19/h3-6,9-10,13-14H,7-8H2,1-2H3/t13-,14+,18+,19+,20-/m0/s1

> <INCHI_KEY>
NSNGIRMJTMEZBF-LZOZONPPSA-N

> <FORMULA>
C20H18O4

> <MOLECULAR_WEIGHT>
322.36

> <EXACT_MASS>
322.12050906

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
42

> <JCHEM_AVERAGE_POLARIZABILITY>
18.777616239816524

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1S,12R,13S,16R,18R)-16,18-dimethyl-2,9-dioxo-17-oxapentacyclo[11.4.1.0^{1,10}.0^{3,8}.0^{12,16}]octadeca-3,5,7,10-tetraene-18-carbaldehyde

> <ALOGPS_LOGP>
2.92

> <JCHEM_LOGP>
2.215542298

> <ALOGPS_LOGS>
-4.32

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-4.306537439790141

> <JCHEM_POLAR_SURFACE_AREA>
60.440000000000005

> <JCHEM_REFRACTIVITY>
88.216

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.53e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1S,12R,13S,16R,18R)-16,18-dimethyl-2,9-dioxo-17-oxapentacyclo[11.4.1.0^{1,10}.0^{3,8}.0^{12,16}]octadeca-3,5,7,10-tetraene-18-carbaldehyde

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 28-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   28-APR-22         0                                  
HETATM    1  C   UNK     0      14.536   0.045   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      14.827   1.557   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      13.664   2.566   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      12.208   2.062   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      11.917   0.550   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      13.080  -0.459   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      10.384   0.130   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0      10.230  -1.403   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       8.949   0.855   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       9.460   2.411   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       8.169   3.336   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       6.901   2.355   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       6.540   0.574   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       7.878  -0.338   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       7.259  -1.748   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       8.170  -2.990   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       8.816  -1.560   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       5.183  -0.272   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       4.247   0.981   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       5.684   1.630   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       7.413   1.322   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       4.971   2.996   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      10.939   2.985   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0      11.137   4.512   0.000  0.00  0.00           O+0
CONECT    1    2    6                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5   23                                                  
CONECT    5    4    6    7                                                  
CONECT    6    5    1                                                       
CONECT    7    5    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10   14   21                                             
CONECT   10    9   11   23                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13   20                                                  
CONECT   13   12   14   18                                                  
CONECT   14   13    9   15   17                                             
CONECT   15   14   16                                                       
CONECT   16   15                                                            
CONECT   17   14                                                            
CONECT   18   13   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   12   21   22                                             
CONECT   21   20    9                                                       
CONECT   22   20                                                            
CONECT   23   10    4   24                                                  
CONECT   24   23                                                            
MASTER        0    0    0    0    0    0    0    0   24    0   56    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₀H₁₈O₄

Average Mass

322.3600 Da

Monoisotopic Mass

322.12051 Da

IUPAC Name

(1S,12R,13S,16R,18R)-16,18-dimethyl-2,9-dioxo-17-oxapentacyclo[11.4.1.0^{1,10}.0^{3,8}.0^{12,16}]octadeca-3,5,7,10-tetraene-18-carbaldehyde

Traditional Name

(1S,12R,13S,16R,18R)-16,18-dimethyl-2,9-dioxo-17-oxapentacyclo[11.4.1.0^{1,10}.0^{3,8}.0^{12,16}]octadeca-3,5,7,10-tetraene-18-carbaldehyde

CAS Registry Number

Not Available

SMILES

C[C@@]12CC[C@H]3[C@H]1C=C1C(=O)C4=CC=CC=C4C(=O)[C@]1(O2)[C@]3(C)C=O

InChI Identifier

InChI=1S/C20H18O4/c1-18(10-21)13-7-8-19(2)14(13)9-15-16(22)11-5-3-4-6-12(11)17(23)20(15,18)24-19/h3-6,9-10,13-14H,7-8H2,1-2H3/t13-,14+,18+,19+,20-/m0/s1

InChI Key

NSNGIRMJTMEZBF-LZOZONPPSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Stereospermum colais	LOTUS Database	35616633
Stereospermum kunthianum	Plant	KNApSAcK
Stereospermum personatum	Plant	KNApSAcK
Sterospermum kunthianum	-	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as anthraquinones. These are organic compounds containing either anthracene-9,10-quinone, 1,4-anthraquinone, or 1,2-anthraquinone.

Kingdom

Super Class

Class

Sub Class

Direct Parent

Alternative Parents

Substituents

Anthraquinone
9,10-anthraquinone
Naphthopyranone
Naphthopyran
Tetralin
Naphthalene
Aryl alkyl ketone
Aryl ketone
Quinone
Pyranone
Oxepane
Pyran
Oxane
Ketone
Oxacycle
Organoheterocyclic compound
Ether
Dialkyl ether
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
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	2.92	ALOGPS
logP	2.22	ChemAxon
logS	-4.3	ALOGPS
pKa (Strongest Basic)	-4.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	60.44 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	88.22 m³·mol⁻¹	ChemAxon
Polarizability	18.78 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

159872786

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Sterekunthal B (NP0075791)

MOL for NP0075791 (Sterekunthal B)

3D MOL for NP0075791 (Sterekunthal B)

3D SDF for NP0075791 (Sterekunthal B)

3D-SDF for NP0075791 (Sterekunthal B)

PDB for NP0075791 (Sterekunthal B)

3D PDB for NP0075791 (Sterekunthal B)

SMILES for NP0075791 (Sterekunthal B)

INCHI for NP0075791 (Sterekunthal B)

Structure for NP0075791 (Sterekunthal B)

3D Structure for NP0075791 (Sterekunthal B)