NP-MRD: Showing NP-Card for Nepetoidin B (NP0074751)

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Record Information

Version

2.0

Created at

2022-04-28 20:04:09 UTC

Updated at

2022-04-28 20:04:09 UTC

NP-MRD ID

NP0074751

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Nepetoidin B

Description

Nepetoidin 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. Nepetoidin B is found in Aeollanthus buchnerianus, Catoferia chiapensis, Cedronella canariensis , Clinopodium vulgare, Cordia sebestena, Dauphinea brevilabra, Endostemon obtusifolius, Eriope macrostachya, Eriope salvifolia, Glechoma hederacea , Hypenia brachystachys, Hyptis eriocephala, Hyptis lanceolata , Hyptis ramosa, Hyptis umbrassa, Hyptis urticoides, Hyssopus officinalis , Lavandula angustifolia, Lavandula angustifolia ssp.delphinensis , Lavandula aristibracteata, Lavandula bipinnata , Lavandula brevidens, Lavandula buchii var.gracile, Lavandula canariensis, Lavandula christiana, Lavandula coronopifolia, Lavandula dentata var.dentata , Lavandula dhofarensis var. dhofarensis, Lavandula lanata , Lavandula latifolia , Lavandula mairei var. mairei, Lavandula maroccana, Lavandula minutolii var.minutolii, Lavandula multifida , Lavandula pubescens, Lavandula rotundifolia, Lavandula ssp.pinnata, Lavandula stoechas ssp.luisieri , Lavandula tenuisecta, Lavandula viridis , Lavandula x allardii, Lavandula x heterophylla, Lycopus exaltatus, Meehania fargesii, Meehania urticifolia, Melissa officinalis , Mentha aquatica , Mentha longifolia , Mentha x villosa, Monarda fistulosa , Nepeta cataria , Ocimum basilicum 'Purple Ruffles' , Ocimum gratissimum , Ocimum selloi , Origanum syriacum , Origanum vulgare , Perilla frutescens , Perrierastrum oreophilum, Plectranthus ambiguus, Plectranthus argentatus, Plectranthus argentifolius, Plectranthus asirensis, Plectranthus barbatus , Plectranthus buchananii, Plectranthus ciliatus, Plectranthus coeruleus, Plectranthus comosus, Plectranthus crassus, Plectranthus cyaneus, Plectranthus cylindraceus , Plectranthus ecklonii, Plectranthus elegans, Plectranthus ernstii, Plectranthus forsteri 'marginatus', Plectranthus frederici, Plectranthus gracilis, Plectranthus grandis, Plectranthus hadiensis, Plectranthus hilliardiae, Plectranthus hyemalis, Plectranthus igniarius, Plectranthus kivuensis, Plectranthus lanuginosus , Plectranthus madagascariensis, Plectranthus mutabilis, Plectranthus neochilus , Plectranthus njassae, Plectranthus oertendahlii, Plectranthus ovatus, Plectranthus parviflorus, Plectranthus petiolaris, Plectranthus pseudomarrubioides, Plectranthus purpuratus, Plectranthus saccatus, Plectranthus sanguineus, Plectranthus spicatus, Plectranthus strigosus, Plectranthus tenuiflorus, Plectranthus xerophilus, Plectranthus zuluensis, Prunella hyssopifolia, Pycnanthemum linifolium, Pycnostachys umbrosa , Rhaphiodon echinus, Salvia nilotica, Salvia digitaloides , Salvia divinorum, Salvia officinalis, Rosmarinus officinalis , Perovskia atriplicifolia, Solenostemon latifolius , Solenostemon shirensis, Tetradenia nervosa, Thorncroftia media and Thymus serpyllum . Nepetoidin B was first documented in 2017 (PMID: 28504466). Based on a literature review a small amount of articles have been published on Nepetoidin B (PMID: 35448815) (PMID: 34439456) (PMID: 32904387) (PMID: 32758576).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 37 38  0  0  0  0  0  0  0  0999 V2000
    0.7141   -3.0317    0.9963 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2408   -1.9367    0.6203 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1600   -0.8024    0.3987 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4457   -0.9612    0.5982 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4045    0.1104    0.3996 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0634    1.3732   -0.0095 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0867    2.3114   -0.1615 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4082    2.0394    0.0753 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4251    2.9527   -0.0702 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7381    0.7634    0.4869 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0702    0.4177    0.7464 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7590   -0.1756    0.6444 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0970   -1.8063    0.4229 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0399   -2.7712    0.5922 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3234   -2.6133    0.3933 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8966   -1.3628   -0.0399 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2891   -1.3604   -0.2065 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9331   -0.2388   -0.6105 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2400    0.9370   -0.8711 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9321    2.0672   -1.2833 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8839    0.9650   -0.7177 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1150    2.0743   -0.9499 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2201   -0.2053   -0.2972 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7924    0.1556    0.0754 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8090   -1.9501    0.9301 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0467    1.6200   -0.2026 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7913    3.2915   -0.4827 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3282    3.9069   -0.3602 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2709   -0.5242    1.0452 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0506   -1.1752    0.9708 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7516   -3.7959    0.9256 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0012   -3.4907    0.5686 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8709   -2.2476   -0.0168 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0090   -0.2596   -0.7325 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4134    2.9055   -1.4662 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4213    2.9634   -1.2459 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1671   -0.1456   -0.1892 H   0  0  0  0  0  0  0  0  0  0  0  0
 20 19  1  0
 19 18  2  0
 18 17  1  0
 17 16  2  0
 16 15  1  0
 15 14  2  0
 14 13  1  0
 13  2  1  0
  2  1  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5 12  2  0
 12 10  1  0
 10 11  1  0
 10  8  2  0
  8  9  1  0
  8  7  1  0
  7  6  2  0
 16 23  1  0
 23 21  2  0
 21 22  1  0
 21 19  1  0
  6  5  1  0
 20 35  1  0
 18 34  1  0
 17 33  1  0
 15 32  1  0
 14 31  1  0
  3 24  1  0
  4 25  1  0
 12 30  1  0
 11 29  1  0
  9 28  1  0
  7 27  1  0
  6 26  1  0
 23 37  1  0
 22 36  1  0
M  END


  Mrv1652304282222042D          

 23 24  0  0  0  0            999 V2000
   -0.7145   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -2.8875    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
   -2.1434   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579   -1.6500    0.0000 O   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
   -3.5724   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0013   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0013   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7158   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4302   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4302   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7158   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1447   -4.1250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7158   -4.9500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579   -4.1250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -4.9500    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  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 10 12  1  0  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
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 14 19  1  0  0  0  0
 17 20  1  0  0  0  0
 16 21  1  0  0  0  0
  3 22  1  0  0  0  0
  2 23  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0074751

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC1=CC=C(\C=C/OC(=O)\C=C\C2=CC(O)=C(O)C=C2)C=C1O

> <INCHI_IDENTIFIER>
InChI=1S/C17H14O6/c18-13-4-1-11(9-15(13)20)3-6-17(22)23-8-7-12-2-5-14(19)16(21)10-12/h1-10,18-21H/b6-3+,8-7-

> <INCHI_KEY>
GFZFUVWXGQWUGX-DGEKEWMVSA-N

> <FORMULA>
C17H14O6

> <MOLECULAR_WEIGHT>
314.293

> <EXACT_MASS>
314.079038171

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
37

> <JCHEM_AVERAGE_POLARIZABILITY>
31.588714324159145

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(Z)-2-(3,4-dihydroxyphenyl)ethenyl (2E)-3-(3,4-dihydroxyphenyl)prop-2-enoate

> <ALOGPS_LOGP>
3.04

> <JCHEM_LOGP>
3.408865729999999

> <ALOGPS_LOGS>
-4.16

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.486361642484862

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.883417780841942

> <JCHEM_PKA_STRONGEST_BASIC>
-6.283784669296016

> <JCHEM_POLAR_SURFACE_AREA>
107.22000000000001

> <JCHEM_REFRACTIVITY>
85.2133

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.17e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(Z)-2-(3,4-dihydroxyphenyl)ethenyl (2E)-3-(3,4-dihydroxyphenyl)prop-2-enoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 28-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   28-APR-22         0                                  
HETATM    1  C   UNK     0      -1.334  -6.930   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -2.667  -7.700   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -4.001  -6.930   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -4.001  -5.390   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -2.667  -4.620   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -1.334  -5.390   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -2.667  -3.080   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -4.001  -2.310   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0      -5.335  -3.080   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0      -6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      -6.668  -0.770   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0      -8.002  -3.080   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -8.002  -4.620   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -9.336  -5.390   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -9.336  -6.930   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0     -10.669  -7.700   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0     -12.003  -6.930   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0     -12.003  -5.390   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0     -10.669  -4.620   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0     -13.337  -7.700   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0     -10.669  -9.240   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0      -5.335  -7.700   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0      -2.667  -9.240   0.000  0.00  0.00           O+0
CONECT    1    2    6                                                       
CONECT    2    1    3   23                                                  
CONECT    3    2    4   22                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6    7                                                  
CONECT    6    5    1                                                       
CONECT    7    5    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15   19                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17   21                                                  
CONECT   17   16   18   20                                                  
CONECT   18   17   19                                                       
CONECT   19   18   14                                                       
CONECT   20   17                                                            
CONECT   21   16                                                            
CONECT   22    3                                                            
CONECT   23    2                                                            
MASTER        0    0    0    0    0    0    0    0   23    0   48    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₇H₁₄O₆

Average Mass

314.2930 Da

Monoisotopic Mass

314.07904 Da

IUPAC Name

(Z)-2-(3,4-dihydroxyphenyl)ethenyl (2E)-3-(3,4-dihydroxyphenyl)prop-2-enoate

Traditional Name

(Z)-2-(3,4-dihydroxyphenyl)ethenyl (2E)-3-(3,4-dihydroxyphenyl)prop-2-enoate

CAS Registry Number

Not Available

SMILES

OC1=CC=C(\C=C/OC(=O)\C=C\C2=CC(O)=C(O)C=C2)C=C1O

InChI Identifier

InChI=1S/C17H14O6/c18-13-4-1-11(9-15(13)20)3-6-17(22)23-8-7-12-2-5-14(19)16(21)10-12/h1-10,18-21H/b6-3+,8-7-

InChI Key

GFZFUVWXGQWUGX-DGEKEWMVSA-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, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, 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
Aeollanthus buchnerianus	Plant	KNApSAcK
Catoferia chiapensis	Plant	KNApSAcK
Cedronella canariensis	Plant	KNApSAcK
Clinopodium vulgare	Plant	KNApSAcK
Cordia sebestena	LOTUS Database	35616633
Dauphinea brevilabra	Plant	KNApSAcK
Endostemon obtusifolius	Plant	KNApSAcK
Eriope macrostachya	Plant	KNApSAcK
Eriope salvifolia	Plant	KNApSAcK
Glechoma hederacea	Plant	KNApSAcK
Hypenia brachystachys	Plant	KNApSAcK
Hyptis eriocephala	Plant	KNApSAcK
Hyptis lanceolata	Plant	KNApSAcK
Hyptis ramosa	Plant	KNApSAcK
Hyptis umbrassa	Plant	KNApSAcK
Hyptis urticoides	Plant	KNApSAcK
Hyssopus officinalis L.	Plant	KNApSAcK
Lavandula angustifolia	LOTUS Database	35616633
Lavandula angustifolia ssp.delphinensis	Plant	KNApSAcK
Lavandula aristibracteata	Plant	KNApSAcK
Lavandula bipinnata	Plant	KNApSAcK
Lavandula brevidens	Plant	KNApSAcK
Lavandula buchii var.gracile	Plant	KNApSAcK
Lavandula canariensis	Plant	KNApSAcK
Lavandula christiana	Plant	KNApSAcK
Lavandula coronopifolia	Plant	KNApSAcK
Lavandula dentata var.dentata	Plant	KNApSAcK
Lavandula dhofarensis var. dhofarensis	Plant	KNApSAcK
Lavandula lanata	Plant	KNApSAcK
Lavandula latifolia	Plant	KNApSAcK
Lavandula mairei var. mairei	Plant	KNApSAcK
Lavandula maroccana	Plant	KNApSAcK
Lavandula minutolii var.minutolii	Plant	KNApSAcK
Lavandula multifida	Plant	KNApSAcK
Lavandula pubescens	Plant	KNApSAcK
Lavandula rotundifolia	Plant	KNApSAcK
Lavandula ssp.pinnata	Plant	KNApSAcK
Lavandula stoechas ssp.luisieri	Plant	KNApSAcK
Lavandula tenuisecta	Plant	KNApSAcK
Lavandula viridis	Plant	KNApSAcK
Lavandula x allardii	Plant	KNApSAcK
Lavandula x heterophylla	Plant	KNApSAcK
Lycopus exaltatus	Plant	KNApSAcK
Meehania fargesii	Plant	KNApSAcK
Meehania urticifolia	LOTUS Database	35616633
Melissa officinalis L.	Plant	KNApSAcK
Mentha aquatica	Plant	KNApSAcK
Mentha longifolia	Plant	KNApSAcK
Mentha x villosa	Plant	KNApSAcK
Monarda fistulosa	Plant	KNApSAcK
Nepeta cataria	Plant	KNApSAcK
Ocimum basilicum 'Purple Ruffles'	Plant	KNApSAcK
Ocimum gratissimum	Plant	KNApSAcK
Ocimum selloi	Plant	KNApSAcK
Origanum syriacum	Plant	KNApSAcK
Origanum vulgare	Plant	KNApSAcK
Perilla frutescens	Plant	KNApSAcK
Perrierastrum oreophilum	Plant	KNApSAcK
Plectranthus ambiguus	Plant	KNApSAcK
Plectranthus argentatus	Plant	KNApSAcK
Plectranthus argentifolius	Plant	KNApSAcK
Plectranthus asirensis	Plant	KNApSAcK
Plectranthus barbatus	Plant	KNApSAcK
Plectranthus buchananii	Plant	KNApSAcK
Plectranthus ciliatus	Plant	KNApSAcK
Plectranthus coeruleus	Plant	KNApSAcK
Plectranthus comosus	Plant	KNApSAcK
Plectranthus crassus	Plant	KNApSAcK
Plectranthus cyaneus	Plant	KNApSAcK
Plectranthus cylindraceus	Plant	KNApSAcK
Plectranthus ecklonii	Plant	KNApSAcK
Plectranthus elegans	Plant	KNApSAcK
Plectranthus ernstii	Plant	KNApSAcK
Plectranthus forsteri 'Marginatus'	Plant	KNApSAcK
Plectranthus frederici	Plant	KNApSAcK
Plectranthus gracilis	Plant	KNApSAcK
Plectranthus grandis	Plant	KNApSAcK
Plectranthus hadiensis	Plant	KNApSAcK
Plectranthus hilliardiae	Plant	KNApSAcK
Plectranthus hyemalis	Plant	KNApSAcK
Plectranthus igniarius	Plant	KNApSAcK
Plectranthus kivuensis	Plant	KNApSAcK
Plectranthus lanuginosus	Plant	KNApSAcK
Plectranthus madagascariensis	Plant	KNApSAcK
Plectranthus mutabilis	Plant	KNApSAcK
Plectranthus neochilus	Plant	KNApSAcK
Plectranthus njassae	Plant	KNApSAcK
Plectranthus oertendahlii	Plant	KNApSAcK
Plectranthus ovatus	Plant	KNApSAcK
Plectranthus parviflorus	Plant	KNApSAcK
Plectranthus petiolaris	Plant	KNApSAcK
Plectranthus pseudomarrubioides	Plant	KNApSAcK
Plectranthus purpuratus	Plant	KNApSAcK
Plectranthus saccatus	Plant	KNApSAcK
Plectranthus sanguineus	Plant	KNApSAcK
Plectranthus spicatus	Plant	KNApSAcK
Plectranthus strigosus	Plant	KNApSAcK
Plectranthus tenuiflorus	Plant	KNApSAcK
Plectranthus xerophilus	Plant	KNApSAcK
Plectranthus zuluensis	Plant	KNApSAcK
Prunella hyssopifolia	Plant	KNApSAcK
Pycnanthemum linifolium	Plant	KNApSAcK
Pycnostachys umbrosa	Plant	KNApSAcK
Rhaphiodon echinus	Plant	KNApSAcK
Salvia nilotica	Plant	KNApSAcK
Salvia digitaloides	Plant	KNApSAcK
Salvia divinorum	LOTUS Database	35616633
Salvia officinalis	Plant	KNApSAcK
Salvia rosmarinus	Plant	KNApSAcK
Salvia yangii	Plant	KNApSAcK
Solenostemon latifolius	Plant	KNApSAcK
Solenostemon shirensis	Plant	KNApSAcK
Tetradenia nervosa	Plant	KNApSAcK
Thorncroftia media	Plant	KNApSAcK
Thymus serpyllum	Plant	KNApSAcK

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

Coumaric acid or derivatives
Cinnamic acid ester
Catechol
Styrene
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Fatty acid ester
Phenol
Monocyclic benzene moiety
Benzenoid
Fatty acyl
Enoate ester
Enol ester
Alpha,beta-unsaturated carboxylic ester
Carboxylic acid ester
Carboxylic acid derivative
Monocarboxylic acid or derivatives
Organic oxide
Organic oxygen compound
Organooxygen compound
Carbonyl group
Hydrocarbon derivative
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	3.04	ALOGPS
logP	3.41	ChemAxon
logS	-4.2	ALOGPS
pKa (Strongest Acidic)	8.88	ChemAxon
pKa (Strongest Basic)	-6.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	107.22 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	85.21 m³·mol⁻¹	ChemAxon
Polarizability	31.59 Å³	ChemAxon
Number of Rings	2	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

C00036175

Chemspider ID

4475793

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

5316819

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Darrag HM, Almuhanna HT, Hakami EH: Secondary Metabolites in Basil, Bio-Insecticide, Inhibition Effect, and In Silico Molecular Docking against Proteolytic Enzymes of the Red Palm Weevil (Rhynchophorus ferrugineus). Plants (Basel). 2022 Apr 16;11(8). pii: plants11081087. doi: 10.3390/plants11081087. [PubMed:35448815 ]
Kim M, Kim JY, Yang HS, Choe JS, Hwang IG: Nepetoidin B from Salvia plebeia R. Br. Inhibits Inflammation by Modulating the NF-kappaB and Nrf2/HO-1 Signaling Pathways in Macrophage Cells. Antioxidants (Basel). 2021 Jul 28;10(8). pii: antiox10081208. doi: 10.3390/antiox10081208. [PubMed:34439456 ]
Nguyen TMH, Le HL, Tran QH, Ha TT, Bui BH, Le NT, Nguyen VH, Nguyen TVA: Data on antiplatelet aggregation, anticoagulation and antioxidant activities of Canna edulis Ker rhizome and its secondary metabolites. Data Brief. 2020 Aug 1;32:106115. doi: 10.1016/j.dib.2020.106115. eCollection 2020 Oct. [PubMed:32904387 ]
Nguyen TMH, Le HL, Ha TT, Bui BH, Le NT, Nguyen VH, Nguyen TVA: Inhibitory effect on human platelet aggregation and coagulation and antioxidant activity of C. edulis Ker Gawl rhizome and its secondary metabolites. J Ethnopharmacol. 2020 Dec 5;263:113136. doi: 10.1016/j.jep.2020.113136. Epub 2020 Aug 3. [PubMed:32758576 ]
Wu X, Gao H, Sun W, Yu J, Hu H, Xu Q, Chen X: Nepetoidin B, a Natural Product, Inhibits LPS-stimulated Nitric Oxide Production via Modulation of iNOS Mediated by NF-kappaB/MKP-5 Pathways. Phytother Res. 2017 Jul;31(7):1072-1077. doi: 10.1002/ptr.5828. Epub 2017 May 15. [PubMed:28504466 ]

Showing NP-Card for Nepetoidin B (NP0074751)

MOL for NP0074751 (Nepetoidin B)

3D MOL for NP0074751 (Nepetoidin B)

3D SDF for NP0074751 (Nepetoidin B)

3D-SDF for NP0074751 (Nepetoidin B)

PDB for NP0074751 (Nepetoidin B)

3D PDB for NP0074751 (Nepetoidin B)

SMILES for NP0074751 (Nepetoidin B)

INCHI for NP0074751 (Nepetoidin B)

Structure for NP0074751 (Nepetoidin B)

3D Structure for NP0074751 (Nepetoidin B)