NP-MRD: Showing NP-Card for (+)-conocarpan (NP0260140)

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Record Information

Version

2.0

Created at

2022-09-08 02:12:46 UTC

Updated at

2022-09-08 02:12:46 UTC

NP-MRD ID

NP0260140

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(+)-conocarpan

Description

(+)-Conocarpan belongs to the class of organic compounds known as 2-arylbenzofuran flavonoids. These are phenylpropanoids containing the 2-phenylbenzofuran moiety (+)-conocarpan 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. (+)-conocarpan is found in Piper aequale and Piper regnellii. (+)-conocarpan was first documented in 2011 (PMID: 21800856). Based on a literature review a small amount of articles have been published on (+)-conocarpan (PMID: 31054997) (PMID: 21783335).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 38 40  0  0  0  0  0  0  0  0999 V2000
    6.4148    1.1037   -0.1395 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9314    0.9030   -0.0388 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4706   -0.3027   -0.3262 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0551   -0.6280   -0.2673 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6765   -1.9225   -0.5881 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3575   -2.3059   -0.5557 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3834   -1.3762   -0.1938 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7130   -0.0805    0.1325 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0666    0.2524    0.0824 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5401    0.6428    0.4665 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.3076    1.4457    1.7307 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4903   -0.4919    0.7387 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.8720   -0.2234    0.3554 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7066   -1.3265    0.1438 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0149   -1.1999   -0.2171 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5664    0.0512   -0.3882 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9175    0.1662   -0.7607 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7640    1.1440   -0.1853 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4316    1.0150    0.1823 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9837   -1.5220   -0.0900 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.7679    0.5057   -0.9991 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6025    2.1819   -0.2893 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9085    0.8173    0.8095 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2929    1.7209    0.2565 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1811   -1.0638   -0.6133 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4329   -2.6482   -0.8702 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0995   -3.3280   -0.8133 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3458    1.2756    0.3380 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8741    1.3130   -0.3369 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2983    2.3423    1.5014 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2328    0.8201    2.4813 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2639    1.7396    2.1681 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3570   -0.7968    1.7931 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3129   -2.3361    0.2678 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6583   -2.0732   -0.3798 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1330    0.1911   -1.7585 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2128    2.1207   -0.3239 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8242    1.8737    0.3354 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7 20  1  0
 20 12  1  0
 12 10  1  0
 10 11  1  0
 10  8  1  0
  8  9  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 16 18  1  0
 18 19  2  0
  9  4  1  0
 19 13  1  0
  8  7  1  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
  2 24  1  0
  3 25  1  0
  5 26  1  0
  6 27  1  0
 12 33  1  1
 10 29  1  6
 11 30  1  0
 11 31  1  0
 11 32  1  0
  9 28  1  0
 14 34  1  0
 15 35  1  0
 17 36  1  0
 18 37  1  0
 19 38  1  0
M  END


  Mrv1652309082204122D          

 20 22  0  0  1  0            999 V2000
    5.4957    2.3479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7812    1.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0668    2.3479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523    1.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523    1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378    0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233    1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233    1.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378    2.3479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387    2.1904    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.8838    2.9750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6538    1.5229    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.1712    1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5837    0.8085    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4087    0.8085    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8212    1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6462    1.5229    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4087    2.2374    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5837    2.2374    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387    0.8555    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  4  9  1  0  0  0  0
  8 10  1  0  0  0  0
 10 11  1  1  0  0  0
 10 12  1  0  0  0  0
 12 13  1  6  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 16 18  1  0  0  0  0
 18 19  2  0  0  0  0
 13 19  1  0  0  0  0
 12 20  1  0  0  0  0
  7 20  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0260140

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C18H18O2/c1-3-4-13-5-10-17-16(11-13)12(2)18(20-17)14-6-8-15(19)9-7-14/h3-12,18-19H,1-2H3/b4-3+/t12-,18-/m0/s1

> <INCHI_KEY>
GXJSAHXNLJFDPO-OFXNJDNMSA-N

> <FORMULA>
C18H18O2

> <MOLECULAR_WEIGHT>
266.34

> <EXACT_MASS>
266.13067982

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
38

> <JCHEM_AVERAGE_POLARIZABILITY>
30.7508064197892

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
4-[(2S,3S)-3-methyl-5-[(1E)-prop-1-en-1-yl]-2,3-dihydro-1-benzofuran-2-yl]phenol

> <JCHEM_LOGP>
4.824447811333334

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.471526318836075

> <JCHEM_PKA_STRONGEST_BASIC>
-4.883510608482652

> <JCHEM_POLAR_SURFACE_AREA>
29.46

> <JCHEM_REFRACTIVITY>
81.9259

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(+)-conocarpan

> <JCHEM_VEBER_RULE>
1

$$$$

HEADER    PROTEIN                                 08-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   08-SEP-22         0                                  
HETATM    1  C   UNK     0      10.259   4.383   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       8.925   3.613   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       7.591   4.383   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       6.258   3.613   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       6.258   2.073   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.924   1.303   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       3.590   2.073   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       3.590   3.613   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.924   4.383   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.126   4.089   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.650   5.553   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.220   2.843   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -0.320   2.843   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -1.090   1.509   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -2.630   1.509   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -3.400   2.843   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      -4.940   2.843   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0      -2.630   4.177   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -1.090   4.177   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       2.126   1.597   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5    9                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8   20                                                  
CONECT    8    7    9   10                                                  
CONECT    9    8    4                                                       
CONECT   10    8   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10   13   20                                                  
CONECT   13   12   14   19                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16   19                                                       
CONECT   19   18   13                                                       
CONECT   20   12    7                                                       
MASTER        0    0    0    0    0    0    0    0   20    0   44    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₈H₁₈O₂

Average Mass

266.3400 Da

Monoisotopic Mass

266.13068 Da

IUPAC Name

4-[(2S,3S)-3-methyl-5-[(1E)-prop-1-en-1-yl]-2,3-dihydro-1-benzofuran-2-yl]phenol

Traditional Name

(+)-conocarpan

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C18H18O2/c1-3-4-13-5-10-17-16(11-13)12(2)18(20-17)14-6-8-15(19)9-7-14/h3-12,18-19H,1-2H3/b4-3+/t12-,18-/m0/s1

InChI Key

GXJSAHXNLJFDPO-OFXNJDNMSA-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
Piper aequale	LOTUS Database	35616633
Piper regnellii	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 2-arylbenzofuran flavonoids. These are phenylpropanoids containing the 2-phenylbenzofuran moiety.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

2-arylbenzofuran flavonoids

Sub Class

Not Available

Direct Parent

2-arylbenzofuran flavonoids

Alternative Parents

Substituents

2-arylbenzofuran flavonoid
Neolignan skeleton
Coumaran
Benzofuran
Styrene
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
Phenol
Monocyclic benzene moiety
Benzenoid
Oxacycle
Ether
Organoheterocyclic compound
Organic oxygen compound
Hydrocarbon derivative
Organooxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

phenols (CHEBI:69251 )
benzofurans (CHEBI:69251 )

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	4.82	ChemAxon
pKa (Strongest Acidic)	9.47	ChemAxon
pKa (Strongest Basic)	-4.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	29.46 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	81.93 m³·mol⁻¹	ChemAxon
Polarizability	30.75 Å³	ChemAxon
Number of Rings	3	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

4976485

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

6474521

PDB ID

Not Available

ChEBI ID

69251

Good Scents ID

Not Available

References

General References

Yang G, Ma H, Wu Y, Zhou B, Zhang C, Chai C, Cao Z: Activation of TRPC6 channels contributes to (+)-conocarpan-induced apoptotic cell death in HK-2 cells. Food Chem Toxicol. 2019 Jul;129:281-290. doi: 10.1016/j.fct.2019.04.061. Epub 2019 May 3. [PubMed:31054997 ]
Baumgartner L, Sosa S, Atanasov AG, Bodensieck A, Fakhrudin N, Bauer J, Favero GD, Ponti C, Heiss EH, Schwaiger S, Ladurner A, Widowitz U, Loggia RD, Rollinger JM, Werz O, Bauer R, Dirsch VM, Tubaro A, Stuppner H: Lignan derivatives from Krameria lappacea roots inhibit acute inflammation in vivo and pro-inflammatory mediators in vitro. J Nat Prod. 2011 Aug 26;74(8):1779-86. doi: 10.1021/np200343t. Epub 2011 Jul 29. [PubMed:21800856 ]
Baumgartner L, Schwaiger S, Stuppner H: Quantitative analysis of anti-inflammatory lignan derivatives in Ratanhiae radix and its tincture by HPLC-PDA and HPLC-MS. J Pharm Biomed Anal. 2011 Nov 1;56(3):546-52. doi: 10.1016/j.jpba.2011.06.016. Epub 2011 Jun 28. [PubMed:21783335 ]
LOTUS database [Link]

Showing NP-Card for (+)-conocarpan (NP0260140)

MOL for NP0260140 ((+)-conocarpan)

3D MOL for NP0260140 ((+)-conocarpan)

3D SDF for NP0260140 ((+)-conocarpan)

3D-SDF for NP0260140 ((+)-conocarpan)

PDB for NP0260140 ((+)-conocarpan)

3D PDB for NP0260140 ((+)-conocarpan)

SMILES for NP0260140 ((+)-conocarpan)

INCHI for NP0260140 ((+)-conocarpan)

Structure for NP0260140 ((+)-conocarpan)

3D Structure for NP0260140 ((+)-conocarpan)