NP-MRD: Showing NP-Card for Strobopinin (NP0050602)

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Record Information

Version

2.0

Created at

2022-04-27 21:58:43 UTC

Updated at

2022-04-27 21:58:43 UTC

NP-MRD ID

NP0050602

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Strobopinin

Description

Strobopinin 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, strobopinin is considered to be a flavonoid. Strobopinin is a secondary metabolite. Secondary metabolites are metabolically or physiologically non-essential metabolites that may serve a role as defense or signalling molecules. In some cases they are simply molecules that arise from the incomplete metabolism of other secondary metabolites. Strobopinin is found in Alnus sieboldiana, Bauhinia purpurea, Leptospermum scoparium , Pentagramma pallida, Pinus bungeana, Pinus krempfii, Pinus monticola, Pinus parviflora, Pinus spp. , Pinus strobus, Piper hostmannianum, Piper hostmannianum var.berbicense, Pityrogramma pallida, Pseudotsuga wilsoniana, Syzygium samarangense and Thelypteris palustris. Strobopinin was first documented in 1957 (PMID: 13465274). Based on a literature review a small amount of articles have been published on strobopinin (PMID: 17397884) (PMID: 33026163) (PMID: 15643565).

Structure

MOL SDF PDB SMILES InChI

  Mrv1652304272223582D          

 20 22  0  0  1  0            999 V2000
   -0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  1  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
    1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -2.4750    0.0000 O   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
    3.5724    1.2375    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
    4.2868   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    0.0000    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  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  4 10  1  0  0  0  0
 10 11  2  0  0  0  0
  8 12  1  6  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 12 17  1  0  0  0  0
  3 18  1  0  0  0  0
  2 19  1  0  0  0  0
  1 20  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0050602

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1=C(O)C=C2O[C@@H](CC(=O)C2=C1O)C1=CC=CC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C16H14O4/c1-9-11(17)7-14-15(16(9)19)12(18)8-13(20-14)10-5-3-2-4-6-10/h2-7,13,17,19H,8H2,1H3/t13-/m0/s1

> <INCHI_KEY>
INBPQAJYHSJVRY-ZDUSSCGKSA-N

> <FORMULA>
C16H14O4

> <MOLECULAR_WEIGHT>
270.284

> <EXACT_MASS>
270.089208931

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
34

> <JCHEM_AVERAGE_POLARIZABILITY>
27.623053037731268

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2S)-5,7-dihydroxy-6-methyl-2-phenyl-3,4-dihydro-2H-1-benzopyran-4-one

> <ALOGPS_LOGP>
3.04

> <JCHEM_LOGP>
3.652094761333333

> <ALOGPS_LOGS>
-3.45

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.7867707442769

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.238992498710479

> <JCHEM_PKA_STRONGEST_BASIC>
-4.939030771246226

> <JCHEM_POLAR_SURFACE_AREA>
66.76

> <JCHEM_REFRACTIVITY>
74.35010000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
9.64e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
strobopinin

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 27-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-APR-22         0                                  
HETATM    1  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.000  -3.080   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.000  -0.000   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       2.667  -0.000   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       2.667  -4.620   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       5.335  -0.000   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       5.335   1.540   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       6.668   2.310   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       8.002   1.540   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       8.002  -0.000   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       0.000  -4.620   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0      -2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0      -2.667   0.000   0.000  0.00  0.00           O+0
CONECT    1    2    6   20                                                  
CONECT    2    1    3   19                                                  
CONECT    3    2    4   18                                                  
CONECT    4    3    5   10                                                  
CONECT    5    4    6    7                                                  
CONECT    6    5    1                                                       
CONECT    7    5    8                                                       
CONECT    8    7    9   12                                                  
CONECT    9    8   10                                                       
CONECT   10    9    4   11                                                  
CONECT   11   10                                                            
CONECT   12    8   13   17                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   12                                                       
CONECT   18    3                                                            
CONECT   19    2                                                            
CONECT   20    1                                                            
MASTER        0    0    0    0    0    0    0    0   20    0   44    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₆H₁₄O₄

Average Mass

270.2840 Da

Monoisotopic Mass

270.08921 Da

IUPAC Name

(2S)-5,7-dihydroxy-6-methyl-2-phenyl-3,4-dihydro-2H-1-benzopyran-4-one

Traditional Name

strobopinin

CAS Registry Number

Not Available

SMILES

CC1=C(O)C=C2O[C@@H](CC(=O)C2=C1O)C1=CC=CC=C1

InChI Identifier

InChI=1S/C16H14O4/c1-9-11(17)7-14-15(16(9)19)12(18)8-13(20-14)10-5-3-2-4-6-10/h2-7,13,17,19H,8H2,1H3/t13-/m0/s1

InChI Key

INBPQAJYHSJVRY-ZDUSSCGKSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Alnus sieboldiana	Plant	KNApSAcK
Bauhinia purpurea	LOTUS Database	35616633
Leptospermum scoparium	Plant	KNApSAcK
Pentagramma pallida	LOTUS Database	35616633
Pinus bungeana	LOTUS Database	35616633
Pinus krempfii	Plant	KNApSAcK
Pinus monticola	LOTUS Database	35616633
Pinus parviflora	LOTUS Database	35616633
Pinus spp.	Plant	KNApSAcK
Pinus strobus	LOTUS Database	35616633
Piper hostmannianum	LOTUS Database	35616633
Piper hostmannianum var.berbicense	Plant	KNApSAcK
Pityrogramma pallida	Plant	KNApSAcK
Pseudotsuga wilsoniana	Plant	KNApSAcK
Syzygium samarangense	LOTUS Database	35616633
Thelypteris palustris	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

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

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

dihydroxyflavanone (CHEBI:9292 )
flavanones (C09939 )
Flavanones (LMPK12140187 )

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	3.04	ALOGPS
logP	3.65	ChemAxon
logS	-3.4	ALOGPS
pKa (Strongest Acidic)	8.24	ChemAxon
pKa (Strongest Basic)	-4.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	66.76 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	74.35 m³·mol⁻¹	ChemAxon
Polarizability	27.62 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

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00001006

Chemspider ID

390946

KEGG Compound ID

C09939

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

442520

PDB ID

Not Available

ChEBI ID

9292

Good Scents ID

rw1588841

References

General References

Portet B, Fabre N, Roumy V, Gornitzka H, Bourdy G, Chevalley S, Sauvain M, Valentin A, Moulis C: Activity-guided isolation of antiplasmodial dihydrochalcones and flavanones from Piper hostmannianum var. berbicense. Phytochemistry. 2007 May;68(9):1312-20. doi: 10.1016/j.phytochem.2007.02.006. Epub 2007 Mar 29. [PubMed:17397884 ]
Xu WJ, Xie X, Wu L, Tian XM, Wang CC, Kong LY, Luo J: Cajuputones A-C, beta-Triketone Flavanone Hybrids from the Branches and Leaves of Melaleuca cajuputi. Chem Biodivers. 2020 Nov;17(11):e2000706. doi: 10.1002/cbdv.202000706. Epub 2020 Oct 27. [PubMed:33026163 ]
Kuo YC, Yang LM, Lin LC: Isolation and immunomodulatory effect of flavonoids from Syzygium samarangense. Planta Med. 2004 Dec;70(12):1237-9. doi: 10.1055/s-2004-835859. [PubMed:15643565 ]
MATSUURA S: The structure of cryptostrobin and strobopinin; the flavanones from the heartwood of Pinus strobus. Pharm Bull. 1957 Jun;5(3):195-8. doi: 10.1248/cpb1953.5.195. [PubMed:13465274 ]

Showing NP-Card for Strobopinin (NP0050602)

MOL for NP0050602 (Strobopinin)

3D MOL for NP0050602 (Strobopinin)

3D SDF for NP0050602 (Strobopinin)

3D-SDF for NP0050602 (Strobopinin)

PDB for NP0050602 (Strobopinin)

3D PDB for NP0050602 (Strobopinin)

SMILES for NP0050602 (Strobopinin)

INCHI for NP0050602 (Strobopinin)

Structure for NP0050602 (Strobopinin)

3D Structure for NP0050602 (Strobopinin)