NP-MRD: Showing NP-Card for (2z)-3-(4-{[(2e)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoyl]oxy}-3-methoxyphenyl)-n-[2-(4-hydroxyphenyl)ethyl]prop-2-enimidic acid (NP0169622)

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Record Information

Version

1.0

Created at

2022-09-03 05:37:06 UTC

Updated at

2022-09-03 05:37:06 UTC

NP-MRD ID

NP0169622

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(2z)-3-(4-{[(2e)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoyl]oxy}-3-methoxyphenyl)-n-[2-(4-hydroxyphenyl)ethyl]prop-2-enimidic acid

Description

Hibicuwanin B belongs to the class of organic compounds known as coumaric acids and derivatives. These are aromatic compounds containing Aromatic compounds containing a cinnamic acid moiety (or a derivative thereof) hydroxylated at the C2 (ortho-), C3 (meta-), or C4 (para-) carbon atom of the benzene ring. (2z)-3-(4-{[(2e)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoyl]oxy}-3-methoxyphenyl)-n-[2-(4-hydroxyphenyl)ethyl]prop-2-enimidic acid is found in Hibiscus taiwanensis. It was first documented in 2022 (PMID: 36057430). Based on a literature review a significant number of articles have been published on Hibicuwanin B (PMID: 36057416) (PMID: 36057403) (PMID: 36057355) (PMID: 36057350).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309032207372D          

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M  END

     RDKit          3D

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M  END


  Mrv1652309032207372D          

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M  END
> <DATABASE_ID>
NP0169622

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC(\C=C\C(=O)OC2=CC=C(\C=C/C(O)=NCCC3=CC=C(O)C=C3)C=C2OC)=CC=C1O

> <INCHI_IDENTIFIER>
InChI=1S/C28H27NO7/c1-34-25-17-20(5-11-23(25)31)8-14-28(33)36-24-12-6-21(18-26(24)35-2)7-13-27(32)29-16-15-19-3-9-22(30)10-4-19/h3-14,17-18,30-31H,15-16H2,1-2H3,(H,29,32)/b13-7-,14-8+

> <INCHI_KEY>
XTBGPZOHAWGAEB-MFUUIURDSA-N

> <FORMULA>
C28H27NO7

> <MOLECULAR_WEIGHT>
489.524

> <EXACT_MASS>
489.178752213

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
63

> <JCHEM_AVERAGE_POLARIZABILITY>
53.085423291438204

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2Z)-3-(4-{[(2E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoyl]oxy}-3-methoxyphenyl)-N-[2-(4-hydroxyphenyl)ethyl]prop-2-enimidic acid

> <ALOGPS_LOGP>
4.96

> <JCHEM_LOGP>
5.126362433950935

> <ALOGPS_LOGS>
-5.64

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.348656699122953

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.237528317242012

> <JCHEM_PKA_STRONGEST_BASIC>
6.209004005435923

> <JCHEM_POLAR_SURFACE_AREA>
117.81000000000002

> <JCHEM_REFRACTIVITY>
138.10490000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
11

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.11e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2Z)-3-(4-{[(2E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoyl]oxy}-3-methoxyphenyl)-N-[2-(4-hydroxyphenyl)ethyl]prop-2-enimidic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 03-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   03-SEP-22         0                                  
HETATM    1  C   UNK     0       4.001 -11.550   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       5.335 -12.320   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       5.335 -13.860   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       6.668 -14.630   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       6.668 -16.170   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       8.002 -16.940   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       8.002 -18.480   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       9.336 -19.250   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0      10.669 -18.480   0.000  0.00  0.00           O+0
HETATM   10  O   UNK     0       9.336 -20.790   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0      10.669 -21.560   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      12.003 -20.790   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      13.337 -21.560   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      13.337 -23.100   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      14.670 -23.870   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      16.004 -23.100   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      16.004 -21.560   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      14.670 -20.790   0.000  0.00  0.00           O+0
HETATM   19  N   UNK     0      17.338 -20.790   0.000  0.00  0.00           N+0
HETATM   20  C   UNK     0      17.338 -19.250   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      18.672 -18.480   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      20.005 -19.250   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      21.339 -18.480   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      22.673 -19.250   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      22.673 -20.790   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0      24.006 -21.560   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0      21.339 -21.560   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      20.005 -20.790   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      12.003 -23.870   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      10.669 -23.100   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0       9.336 -23.870   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0       8.002 -23.100   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       5.335 -16.940   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       4.001 -16.170   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       4.001 -14.630   0.000  0.00  0.00           C+0
HETATM   36  O   UNK     0       2.667 -13.860   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   35                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6   33                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11                                                       
CONECT   11   10   12   30                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15   29                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   23   28                                                  
CONECT   23   22   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24   26   27                                                  
CONECT   26   25                                                            
CONECT   27   25   28                                                       
CONECT   28   27   22                                                       
CONECT   29   14   30                                                       
CONECT   30   29   11   31                                                  
CONECT   31   30   32                                                       
CONECT   32   31                                                            
CONECT   33    5   34                                                       
CONECT   34   33   35                                                       
CONECT   35   34    3   36                                                  
CONECT   36   35                                                            
MASTER        0    0    0    0    0    0    0    0   36    0   76    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₈H₂₇NO₇

Average Mass

489.5240 Da

Monoisotopic Mass

489.17875 Da

IUPAC Name

(2Z)-3-(4-{[(2E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoyl]oxy}-3-methoxyphenyl)-N-[2-(4-hydroxyphenyl)ethyl]prop-2-enimidic acid

Traditional Name

(2Z)-3-(4-{[(2E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoyl]oxy}-3-methoxyphenyl)-N-[2-(4-hydroxyphenyl)ethyl]prop-2-enimidic acid

CAS Registry Number

Not Available

SMILES

COC1=CC(\C=C\C(=O)OC2=CC=C(\C=C/C(O)=NCCC3=CC=C(O)C=C3)C=C2OC)=CC=C1O

InChI Identifier

InChI=1S/C28H27NO7/c1-34-25-17-20(5-11-23(25)31)8-14-28(33)36-24-12-6-21(18-26(24)35-2)7-13-27(32)29-16-15-19-3-9-22(30)10-4-19/h3-14,17-18,30-31H,15-16H2,1-2H3,(H,29,32)/b13-7-,14-8+

InChI Key

XTBGPZOHAWGAEB-MFUUIURDSA-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
Hibiscus taiwanensis	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as coumaric acids and derivatives. These are aromatic compounds containing Aromatic compounds containing a cinnamic acid moiety (or a derivative thereof) hydroxylated at the C2 (ortho-), C3 (meta-), or C4 (para-) carbon atom of the benzene ring.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Cinnamic acids and derivatives

Sub Class

Hydroxycinnamic acids and derivatives

Direct Parent

Coumaric acids and derivatives

Alternative Parents

Substituents

Cinnamic acid amide
Coumaric acid or derivatives
Cinnamic acid ester
Methoxyphenol
Phenol ester
Methoxybenzene
Styrene
Phenoxy compound
Phenol ether
Anisole
1-hydroxy-2-unsubstituted benzenoid
Phenol
Fatty acid ester
Alkyl aryl ether
Monocyclic benzene moiety
Fatty acyl
Benzenoid
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Carboxamide group
Carboxylic acid ester
Secondary carboxylic acid amide
Ether
Carboxylic acid derivative
Monocarboxylic acid or derivatives
Organic nitrogen compound
Organic oxide
Organic oxygen compound
Carbonyl group
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic 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	4.96	ALOGPS
logP	5.13	ChemAxon
logS	-5.6	ALOGPS
pKa (Strongest Acidic)	4.24	ChemAxon
pKa (Strongest Basic)	6.21	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	117.81 Å²	ChemAxon
Rotatable Bond Count	11	ChemAxon
Refractivity	138.1 m³·mol⁻¹	ChemAxon
Polarizability	53.09 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	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

4438898

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

5274620

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Delahunt A, Conway MC, Callaghan SL, O'Brien EC, Geraghty AA, O'Reilly SL, McDonnell CM, Mehegan J, McAuliffe FM: Maternal dietary quality during pregnancy and child appetitive traits at 5-years-old: Findings from the ROLO longitudinal birth cohort study. Appetite. 2022 Aug 31;179:106291. doi: 10.1016/j.appet.2022.106291. [PubMed:36057430 ]
Oliveira FADS, de Holanda MV, Lima LB, Dantas MB, Duarte IO, de Castro LGZ, de Oliveira LLB, Paier CRK, Moreira-Nunes CFA, Lima NCB, Melo VMM, Montenegro RC: Genomic Surveillance: Circulating lineages and genomic variation of SARS-CoV-2 in early pandemic in Ceara state, Northeast Brazil. Virus Res. 2022 Aug 31:198908. doi: 10.1016/j.virusres.2022.198908. [PubMed:36057416 ]
Marszalek-Grabska M, Zakrocka I, Budzynska B, Marciniak S, Kaszubska K, Lemieszek MK, Winiarczyk S, Kotlinska JH, Rzeski W, Turski WA: Binge-like mephedrone treatment induces memory impairment concomitant with brain kynurenic acid reduction in mice. Toxicol Appl Pharmacol. 2022 Aug 31;454:116216. doi: 10.1016/j.taap.2022.116216. [PubMed:36057403 ]
Rajivgandhi G, Ramachandran G, Chackaravarthi G, Maruthupandy M, Quero F, Chelliah CK, Manoharan N, Alharbi NS, Kadaikunnan S, Khaled JM, Li WJ: Metal tolerance and biosorption of Pb ions by Bacillus cereus RMN 1 (MK521259) isolated from metal contaminated sites. Chemosphere. 2022 Aug 31;308(Pt 1):136270. doi: 10.1016/j.chemosphere.2022.136270. [PubMed:36057355 ]
Saravanan S, Carolin C F, Kumar PS, Chitra B, Rangasamy G: Biodegradation of textile dye Rhodamine-B by Brevundimonas diminuta and screening of their breakdown metabolites. Chemosphere. 2022 Aug 31;308(Pt 1):136266. doi: 10.1016/j.chemosphere.2022.136266. [PubMed:36057350 ]
LOTUS database [Link]

Showing NP-Card for (2z)-3-(4-{[(2e)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoyl]oxy}-3-methoxyphenyl)-n-[2-(4-hydroxyphenyl)ethyl]prop-2-enimidic acid (NP0169622)

MOL for NP0169622 ((2z)-3-(4-{[(2e)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoyl]oxy}-3-methoxyphenyl)-n-[2-(4-hydroxyphenyl)ethyl]prop-2-enimidic acid)

3D MOL for NP0169622 ((2z)-3-(4-{[(2e)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoyl]oxy}-3-methoxyphenyl)-n-[2-(4-hydroxyphenyl)ethyl]prop-2-enimidic acid)

3D SDF for NP0169622 ((2z)-3-(4-{[(2e)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoyl]oxy}-3-methoxyphenyl)-n-[2-(4-hydroxyphenyl)ethyl]prop-2-enimidic acid)

3D-SDF for NP0169622 ((2z)-3-(4-{[(2e)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoyl]oxy}-3-methoxyphenyl)-n-[2-(4-hydroxyphenyl)ethyl]prop-2-enimidic acid)

PDB for NP0169622 ((2z)-3-(4-{[(2e)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoyl]oxy}-3-methoxyphenyl)-n-[2-(4-hydroxyphenyl)ethyl]prop-2-enimidic acid)

3D PDB for NP0169622 ((2z)-3-(4-{[(2e)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoyl]oxy}-3-methoxyphenyl)-n-[2-(4-hydroxyphenyl)ethyl]prop-2-enimidic acid)

SMILES for NP0169622 ((2z)-3-(4-{[(2e)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoyl]oxy}-3-methoxyphenyl)-n-[2-(4-hydroxyphenyl)ethyl]prop-2-enimidic acid)

INCHI for NP0169622 ((2z)-3-(4-{[(2e)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoyl]oxy}-3-methoxyphenyl)-n-[2-(4-hydroxyphenyl)ethyl]prop-2-enimidic acid)

Structure for NP0169622 ((2z)-3-(4-{[(2e)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoyl]oxy}-3-methoxyphenyl)-n-[2-(4-hydroxyphenyl)ethyl]prop-2-enimidic acid)

3D Structure for NP0169622 ((2z)-3-(4-{[(2e)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoyl]oxy}-3-methoxyphenyl)-n-[2-(4-hydroxyphenyl)ethyl]prop-2-enimidic acid)