NP-MRD: Showing NP-Card for Lochnocarpol A (NP0046592)

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Record Information

Version

2.0

Created at

2022-03-17 20:08:25 UTC

Updated at

2022-03-17 20:08:25 UTC

NP-MRD ID

NP0046592

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Lochnocarpol A

Description

Lochnocarpol A is found in Citrus medica, Citrus natsudaidai, Citrus nobilis, Citrus spp., Erythrina fusca , Erythrina senegalensis , Flemingia macrophylla, Glycyrrhiza pallidiflora, Humulus lupulus , Limonia acidissima, Lonchocarpus miniflorus, Lonchocarpus minimiflorus, Lupinus luteus , Macaranga conifera and Sophora tetraptera .

Structure

MOL SDF PDB SMILES InChI

6,8-Diprenylnaringenin
  Mrv1572001071617292D          

 30 32  0  0  1  0            999 V2000
    5.8309  -11.9866    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4027  -14.4585    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9676  -11.9832    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8205  -14.4619    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.4082  -10.7610    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1098  -13.2191    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1133  -12.3952    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4027  -11.9832    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4027  -13.6345    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6851  -13.2191    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6851  -12.3952    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8240  -13.6380    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5449  -12.3986    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5415  -13.2260    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2624  -11.9934    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4027  -11.1558    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9676  -13.6345    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9697  -12.4089    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2659  -11.1696    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1133  -10.7439    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2569  -13.2191    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6871  -12.0003    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9765  -10.7576    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6906  -11.1730    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1133   -9.9233    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5429  -13.6345    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8240   -9.5113    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4027   -9.5113    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8254  -13.2191    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5429  -14.4619    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  7  1  0  0  0  0
  1 13  1  0  0  0  0
  2  9  1  0  0  0  0
  3 11  1  0  0  0  0
  4 12  2  0  0  0  0
  5 24  1  0  0  0  0
  6  7  2  0  0  0  0
  6  9  1  0  0  0  0
  6 12  1  0  0  0  0
  7  8  1  0  0  0  0
  8 11  2  0  0  0  0
  8 16  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 10 17  1  0  0  0  0
 12 14  1  0  0  0  0
 13 14  1  0  0  0  0
 13 15  1  0  0  0  0
 15 18  2  0  0  0  0
 15 19  1  0  0  0  0
 16 20  1  0  0  0  0
 17 21  1  0  0  0  0
 18 22  1  0  0  0  0
 19 23  2  0  0  0  0
 20 25  2  0  0  0  0
 21 26  2  0  0  0  0
 22 24  2  0  0  0  0
 23 24  1  0  0  0  0
 25 27  1  0  0  0  0
 25 28  1  0  0  0  0
 26 29  1  0  0  0  0
 26 30  1  0  0  0  0
M  END

6,8-Diprenylnaringenin
  Mrv1572001071617292D          

 30 32  0  0  1  0            999 V2000
    5.8309  -11.9866    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4027  -14.4585    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9676  -11.9832    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8205  -14.4619    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.4082  -10.7610    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1098  -13.2191    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1133  -12.3952    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4027  -11.9832    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4027  -13.6345    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6851  -13.2191    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6851  -12.3952    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8240  -13.6380    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5449  -12.3986    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5415  -13.2260    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2624  -11.9934    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4027  -11.1558    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9676  -13.6345    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9697  -12.4089    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2659  -11.1696    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1133  -10.7439    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2569  -13.2191    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6871  -12.0003    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9765  -10.7576    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6906  -11.1730    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1133   -9.9233    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5429  -13.6345    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8240   -9.5113    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4027   -9.5113    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8254  -13.2191    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5429  -14.4619    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  7  1  0  0  0  0
  1 13  1  0  0  0  0
  2  9  1  0  0  0  0
  3 11  1  0  0  0  0
  4 12  2  0  0  0  0
  5 24  1  0  0  0  0
  6  7  2  0  0  0  0
  6  9  1  0  0  0  0
  6 12  1  0  0  0  0
  7  8  1  0  0  0  0
  8 11  2  0  0  0  0
  8 16  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 10 17  1  0  0  0  0
 12 14  1  0  0  0  0
 13 14  1  0  0  0  0
 13 15  1  0  0  0  0
 15 18  2  0  0  0  0
 15 19  1  0  0  0  0
 16 20  1  0  0  0  0
 17 21  1  0  0  0  0
 18 22  1  0  0  0  0
 19 23  2  0  0  0  0
 20 25  2  0  0  0  0
 21 26  2  0  0  0  0
 22 24  2  0  0  0  0
 23 24  1  0  0  0  0
 25 27  1  0  0  0  0
 25 28  1  0  0  0  0
 26 29  1  0  0  0  0
 26 30  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0046592

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)=CCC1=C(O)C2=C(OC(CC2=O)C2=CC=C(O)C=C2)C(CC=C(C)C)=C1O

> <INCHI_IDENTIFIER>
InChI=1S/C25H28O5/c1-14(2)5-11-18-23(28)19(12-6-15(3)4)25-22(24(18)29)20(27)13-21(30-25)16-7-9-17(26)10-8-16/h5-10,21,26,28-29H,11-13H2,1-4H3

> <INCHI_KEY>
HCNLDGTUMBOHKT-UHFFFAOYSA-N

> <FORMULA>
C25H28O5

> <MOLECULAR_WEIGHT>
408.494

> <EXACT_MASS>
408.193674002

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
58

> <JCHEM_AVERAGE_POLARIZABILITY>
45.31907803086477

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
5,7-dihydroxy-2-(4-hydroxyphenyl)-6,8-bis(3-methylbut-2-en-1-yl)-3,4-dihydro-2H-1-benzopyran-4-one

> <ALOGPS_LOGP>
4.50

> <JCHEM_LOGP>
6.292242049000001

> <ALOGPS_LOGS>
-4.85

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.070829382591645

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.508271233960288

> <JCHEM_PKA_STRONGEST_BASIC>
-4.961077727446398

> <JCHEM_POLAR_SURFACE_AREA>
86.99

> <JCHEM_REFRACTIVITY>
119.7754

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
5.75e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
5,7-dihydroxy-2-(4-hydroxyphenyl)-6,8-bis(3-methylbut-2-en-1-yl)-2,3-dihydro-1-benzopyran-4-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 07-JAN-16   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 6,8-Diprenylnaringenin                            
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   07-JAN-16         0                                  
HETATM    1  O   UNK     0      10.884 -22.375   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0       8.218 -26.989   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0       5.540 -22.369   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0      10.865 -26.996   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0      17.562 -20.087   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       9.538 -24.676   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       9.545 -23.138   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       8.218 -22.369   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       8.218 -25.451   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       6.879 -24.676   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       6.879 -23.138   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      10.871 -25.458   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      12.217 -23.144   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      12.211 -24.689   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      13.556 -22.388   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       8.218 -20.824   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       5.540 -25.451   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      14.877 -23.163   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      13.563 -20.850   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       9.545 -20.055   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       4.213 -24.676   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      16.216 -22.401   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      14.889 -20.081   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      16.222 -20.856   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       9.545 -18.523   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       2.880 -25.451   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      10.871 -17.754   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       8.218 -17.754   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       1.541 -24.676   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       2.880 -26.996   0.000  0.00  0.00           C+0
CONECT    1    7   13                                                       
CONECT    2    9                                                            
CONECT    3   11                                                            
CONECT    4   12                                                            
CONECT    5   24                                                            
CONECT    6    7    9   12                                                  
CONECT    7    1    6    8                                                  
CONECT    8    7   11   16                                                  
CONECT    9    2    6   10                                                  
CONECT   10    9   11   17                                                  
CONECT   11    3    8   10                                                  
CONECT   12    4    6   14                                                  
CONECT   13    1   14   15                                                  
CONECT   14   12   13                                                       
CONECT   15   13   18   19                                                  
CONECT   16    8   20                                                       
CONECT   17   10   21                                                       
CONECT   18   15   22                                                       
CONECT   19   15   23                                                       
CONECT   20   16   25                                                       
CONECT   21   17   26                                                       
CONECT   22   18   24                                                       
CONECT   23   19   24                                                       
CONECT   24    5   22   23                                                  
CONECT   25   20   27   28                                                  
CONECT   26   21   29   30                                                  
CONECT   27   25                                                            
CONECT   28   25                                                            
CONECT   29   26                                                            
CONECT   30   26                                                            
MASTER        0    0    0    0    0    0    0    0   30    0   64    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₅H₂₈O₅

Average Mass

408.4940 Da

Monoisotopic Mass

408.19367 Da

IUPAC Name

5,7-dihydroxy-2-(4-hydroxyphenyl)-6,8-bis(3-methylbut-2-en-1-yl)-3,4-dihydro-2H-1-benzopyran-4-one

Traditional Name

5,7-dihydroxy-2-(4-hydroxyphenyl)-6,8-bis(3-methylbut-2-en-1-yl)-2,3-dihydro-1-benzopyran-4-one

CAS Registry Number

Not Available

SMILES

CC(C)=CCC1=C(O)C2=C(OC(CC2=O)C2=CC=C(O)C=C2)C(CC=C(C)C)=C1O

InChI Identifier

InChI=1S/C25H28O5/c1-14(2)5-11-18-23(28)19(12-6-15(3)4)25-22(24(18)29)20(27)13-21(30-25)16-7-9-17(26)10-8-16/h5-10,21,26,28-29H,11-13H2,1-4H3

InChI Key

HCNLDGTUMBOHKT-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Citrus medica	LOTUS Database	35616633
Citrus natsudaidai	LOTUS Database	35616633
Citrus nobilis	LOTUS Database	35616633
Citrus spp.	Plant	KNApSAcK
Citrus X sinensis (L.) Osbeck (pro. sp.)	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Erythrina fusca	Plant	KNApSAcK
Erythrina senegalensis	Plant	KNApSAcK
Flemingia macrophylla	LOTUS Database	35616633
Glycyrrhiza pallidiflora	LOTUS Database	35616633
Humulus lupulus	Plant	KNApSAcK
Limonia acidissima	LOTUS Database	35616633
Lonchocarpus miniflorus	Plant	KNApSAcK
Lonchocarpus minimiflorus	LOTUS Database	35616633
Lupinus luteus	Plant	KNApSAcK
Macaranga conifera	Plant	KNApSAcK
Sophora tetraptera	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 8-prenylated flavanones. These are flavanones that features a C5-isoprenoid substituent at the 8-position.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Flavonoids

Sub Class

Flavans

Direct Parent

8-prenylated flavanones

Alternative Parents

Substituents

6-prenylated flavanone
8-prenylated flavanone
6-prenylated flavan
4'-hydroxyflavonoid
5-hydroxyflavonoid
7-hydroxyflavonoid
Flavanone
Hydroxyflavonoid
Chromone
Chromane
Benzopyran
1-benzopyran
Aryl alkyl ketone
Aryl ketone
Phenol
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
Monocyclic benzene moiety
Benzenoid
Vinylogous acid
Ketone
Ether
Organoheterocyclic compound
Oxacycle
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
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	4.5	ALOGPS
logP	6.29	ChemAxon
logS	-4.8	ALOGPS
pKa (Strongest Acidic)	7.51	ChemAxon
pKa (Strongest Basic)	-5	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	86.99 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	119.78 m³·mol⁻¹	ChemAxon
Polarizability	45.32 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	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

FDB005123

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

3951

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Lochnocarpol A (NP0046592)

MOL for NP0046592 (Lochnocarpol A)

3D MOL for NP0046592 (Lochnocarpol A)

3D SDF for NP0046592 (Lochnocarpol A)

3D-SDF for NP0046592 (Lochnocarpol A)

PDB for NP0046592 (Lochnocarpol A)

3D PDB for NP0046592 (Lochnocarpol A)

SMILES for NP0046592 (Lochnocarpol A)

INCHI for NP0046592 (Lochnocarpol A)

Structure for NP0046592 (Lochnocarpol A)

3D Structure for NP0046592 (Lochnocarpol A)