NP-MRD: Showing NP-Card for Steppogenin (NP0140069)

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Record Information

Version

2.0

Created at

2022-06-29 20:44:39 UTC

Updated at

2022-06-29 20:44:39 UTC

NP-MRD ID

NP0140069

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Steppogenin

Description

Norartocarpanone belongs to the class of organic compounds known as flavanones. Flavanones are compounds containing a flavan-3-one moiety, with a structure characterized by a 2-phenyl-3,4-dihydro-2H-1-benzopyran bearing a ketone at the carbon C3. Thus, norartocarpanone is considered to be a flavonoid lipid molecule. Norartocarpanone is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Outside of the human body, Norartocarpanone has been detected, but not quantified in, fruits. Steppogenin is found in Artocarpus altilis, Artocarpus dadah, Bagassa guianensis, Broussonetia papyrifera, Euphorbia stepposa, Ficus subcuneata, Maclura pomifera, Maclura tinctoria, Morus alba and Morus lhou. This could make norartocarpanone a potential biomarker for the consumption of these foods.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 33 35  0  0  0  0  0  0  0  0999 V2000
   -1.1695    1.5853   -2.3197 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1569    1.2377   -1.1366 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1598    1.7355   -0.1790 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3588    0.6469    0.7307 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.7768    0.3185    0.3835 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3149    0.5703   -0.8549 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6380    0.2301   -1.1579 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4565   -0.3693   -0.2332 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7863   -0.7057   -0.5379 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9278   -0.6281    1.0126 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6029   -0.2852    1.3099 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0801   -0.5546    2.5784 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4578   -0.5161    0.7000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7550   -0.6166    0.2955 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6770   -1.5264    0.7622 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9750   -1.5650    0.3084 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8855   -2.5170    0.8146 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3852   -0.6734   -0.6445 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4655    0.2597   -1.1352 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8552    1.1664   -2.0943 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1832    0.2852   -0.6764 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6473    2.2654   -0.6863 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6410    2.5652    0.4511 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3084    1.0293    1.7738 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7049    1.0229   -1.6214 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0340    0.4375   -2.1357 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4879    0.0295   -0.3414 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5361   -1.0918    1.7640 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6385   -0.9860    3.3067 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3681   -2.2416    1.5113 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4584   -2.3395    1.6014 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3754   -0.6507   -1.0395 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3308    1.8819   -2.5099 H   0  0  0  0  0  0  0  0  0  0  0  0
  9  8  1  0
  8 10  2  0
 10 11  1  0
 11 12  1  0
 11  5  2  0
  5  6  1  0
  6  7  2  0
  5  4  1  0
  4  3  1  0
  3  2  1  0
  2  1  2  0
  2 21  1  0
 21 19  2  0
 19 20  1  0
 19 18  1  0
 18 16  2  0
 16 17  1  0
 16 15  1  0
 15 14  2  0
 14 13  1  0
  7  8  1  0
 13  4  1  0
 14 21  1  0
  9 27  1  0
 10 28  1  0
 12 29  1  0
  6 25  1  0
  7 26  1  0
  4 24  1  1
  3 22  1  0
  3 23  1  0
 20 33  1  0
 18 32  1  0
 17 31  1  0
 15 30  1  0
M  END


  Mrv0541 05061309422D          

 21 23  0  0  0  0            999 V2000
    6.4302   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0  0  0  0
  7  1  1  0  0  0  0
  7  3  2  0  0  0  0
  8  4  2  0  0  0  0
  8  5  1  0  0  0  0
  9  2  1  0  0  0  0
 10  3  1  0  0  0  0
 10  9  2  0  0  0  0
 11  4  1  0  0  0  0
 12  6  1  0  0  0  0
 13  6  1  0  0  0  0
 13  9  1  0  0  0  0
 14  5  2  0  0  0  0
 15 11  2  0  0  0  0
 15 12  1  0  0  0  0
 15 14  1  0  0  0  0
 16  7  1  0  0  0  0
 17  8  1  0  0  0  0
 18 10  1  0  0  0  0
 19 11  1  0  0  0  0
 20 12  2  0  0  0  0
 21 13  1  0  0  0  0
 21 14  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0140069

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC1=CC(O)=C(C=C1)C1CC(=O)C2=C(O)C=C(O)C=C2O1

> <INCHI_IDENTIFIER>
InChI=1S/C15H12O6/c16-7-1-2-9(10(18)3-7)13-6-12(20)15-11(19)4-8(17)5-14(15)21-13/h1-5,13,16-19H,6H2

> <INCHI_KEY>
QBLQLKNOKUHRCH-UHFFFAOYSA-N

> <FORMULA>
C15H12O6

> <MOLECULAR_WEIGHT>
288.2522

> <EXACT_MASS>
288.063388116

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_AVERAGE_POLARIZABILITY>
28.133123006983936

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-(2,4-dihydroxyphenyl)-5,7-dihydroxy-3,4-dihydro-2H-1-benzopyran-4-one

> <ALOGPS_LOGP>
2.07

> <JCHEM_LOGP>
2.5315427286666665

> <ALOGPS_LOGS>
-2.91

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
8.99310761379941

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.884122376979166

> <JCHEM_PKA_STRONGEST_BASIC>
-3.86132469771466

> <JCHEM_POLAR_SURFACE_AREA>
107.22000000000001

> <JCHEM_REFRACTIVITY>
73.2707

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.53e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
steppogenin

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 06-MAY-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAY-13         0                                  
HETATM    1  C   UNK     0      12.003  -0.770   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      10.669   0.000   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      10.669  -3.080   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       8.002   1.540   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      12.003  -2.310   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       9.336  -0.770   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       9.336  -2.310   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.001   2.310   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       6.668   2.310   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       8.002   0.000   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       5.335   1.540   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      13.337  -3.080   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0       1.334  -0.770   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0       8.002  -3.080   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0       4.001   3.850   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0       6.668   3.850   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0       6.668  -0.770   0.000  0.00  0.00           O+0
CONECT    1    2    7                                                       
CONECT    2    1    9                                                       
CONECT    3    7   10                                                       
CONECT    4    8   11                                                       
CONECT    5    8   14                                                       
CONECT    6   12   13                                                       
CONECT    7    1    3   16                                                  
CONECT    8    4    5   17                                                  
CONECT    9    2   10   13                                                  
CONECT   10    3    9   18                                                  
CONECT   11    4   15   19                                                  
CONECT   12    6   15   20                                                  
CONECT   13    6    9   21                                                  
CONECT   14    5   15   21                                                  
CONECT   15   11   12   14                                                  
CONECT   16    7                                                            
CONECT   17    8                                                            
CONECT   18   10                                                            
CONECT   19   11                                                            
CONECT   20   12                                                            
CONECT   21   13   14                                                       
MASTER        0    0    0    0    0    0    0    0   21    0   46    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₅H₁₂O₆

Average Mass

288.2522 Da

Monoisotopic Mass

288.06339 Da

IUPAC Name

2-(2,4-dihydroxyphenyl)-5,7-dihydroxy-3,4-dihydro-2H-1-benzopyran-4-one

Traditional Name

steppogenin

CAS Registry Number

Not Available

SMILES

OC1=CC(O)=C(C=C1)C1CC(=O)C2=C(O)C=C(O)C=C2O1

InChI Identifier

InChI=1S/C15H12O6/c16-7-1-2-9(10(18)3-7)13-6-12(20)15-11(19)4-8(17)5-14(15)21-13/h1-5,13,16-19H,6H2

InChI Key

QBLQLKNOKUHRCH-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
Artocarpus altilis	LOTUS Database	35616633
Artocarpus dadah	LOTUS Database	35616633
Bagassa guianensis	LOTUS Database	35616633
Broussonetia papyrifera	LOTUS Database	35616633
Euphorbia stepposa	LOTUS Database	35616633
Ficus subcuneata	LOTUS Database	35616633
Maclura pomifera	LOTUS Database	35616633
Maclura tinctoria	LOTUS Database	35616633
Morus alba	LOTUS Database	35616633
Morus lhou	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as flavanones. Flavanones are compounds containing a flavan-3-one moiety, with a structure characterized by a 2-phenyl-3,4-dihydro-2H-1-benzopyran bearing a ketone at the carbon C3.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Flavonoids

Sub Class

Flavans

Direct Parent

Flavanones

Alternative Parents

Substituents

4'-hydroxyflavonoid
5-hydroxyflavonoid
7-hydroxyflavonoid
Flavanone
Hydroxyflavonoid
Chromone
Chromane
Benzopyran
1-benzopyran
Aryl alkyl ketone
Aryl ketone
Resorcinol
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
Phenol
Monocyclic benzene moiety
Benzenoid
Vinylogous acid
Ketone
Organoheterocyclic compound
Ether
Oxacycle
Hydrocarbon derivative
Organic oxide
Organooxygen compound
Organic oxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Flavanones (LMPK12140533 )

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	2.07	ALOGPS
logP	2.53	ChemAxon
logS	-2.9	ALOGPS
pKa (Strongest Acidic)	7.88	ChemAxon
pKa (Strongest Basic)	-3.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	107.22 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	73.27 m³·mol⁻¹	ChemAxon
Polarizability	28.13 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

HMDB0037314

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB016333

KNApSAcK ID

C00008367

Chemspider ID

10221696

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

21596130

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Steppogenin (NP0140069)

MOL for NP0140069 (Steppogenin)

3D MOL for NP0140069 (Steppogenin)

3D SDF for NP0140069 (Steppogenin)

3D-SDF for NP0140069 (Steppogenin)

PDB for NP0140069 (Steppogenin)

3D PDB for NP0140069 (Steppogenin)

SMILES for NP0140069 (Steppogenin)

INCHI for NP0140069 (Steppogenin)

Structure for NP0140069 (Steppogenin)

3D Structure for NP0140069 (Steppogenin)