NP-MRD: Showing NP-Card for ngaione (-) (NP0204880)

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Record Information

Version

2.0

Created at

2022-09-05 00:39:50 UTC

Updated at

2022-09-05 00:39:50 UTC

NP-MRD ID

NP0204880

Secondary Accession Numbers

None

Natural Product Identification

Common Name

ngaione (-)

Description

Ngaione (-), also known as ipomeamarone, belongs to the class of organic compounds known as heteroaromatic compounds. Heteroaromatic compounds are compounds containing an aromatic ring where a carbon atom is linked to an hetero atom. Thus, ngaione (-) is considered to be an isoprenoid. ngaione (-) is found in Eremophila deserti and Myoporum laetum. ngaione (-) was first documented in 2007 (PMID: 17603183). Based on a literature review a small amount of articles have been published on Ngaione (-) (PMID: 35702877) (PMID: 35804741) (PMID: 30963521) (PMID: 25418792).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 40 41  0  0  0  0  0  0  0  0999 V2000
    3.9856    1.4974    0.7070 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9873    0.1044    0.0853 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2889   -0.5534    0.4942 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8540   -0.7308    0.6061 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5257   -0.1401    0.3190 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1273    0.7836    1.0025 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6441   -0.6199   -0.7701 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6493    0.1562   -0.8401 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.4495    1.6195   -1.0845 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4590   -0.4897   -1.9752 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7201   -0.9259   -1.2419 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7077    0.1081   -0.1208 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.7323   -0.1218    0.8854 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8989   -0.8747    0.8314 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5258   -0.7596    2.0724 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7879    0.0096    2.8222 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7093    0.4130    2.1569 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4072   -0.0001    0.3168 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2232    2.1461    0.2412 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8408    1.4074    1.8225 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9688    1.9936    0.5707 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9327    0.2645   -1.0110 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1308    0.1768    0.5382 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5321   -1.3651   -0.2253 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1926   -1.0023    1.4982 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8928   -1.7072    0.0644 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0192   -0.8879    1.6931 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3634   -1.7013   -0.6257 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2008   -0.5947   -1.7258 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6112    1.9191   -0.9707 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7324    1.9135   -2.1266 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0187    2.2570   -0.3466 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9344   -1.3102   -2.4616 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7791    0.3134   -2.6809 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6109   -0.8469   -1.8778 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6067   -1.9571   -0.8490 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9135    1.0913   -0.6239 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2381   -1.4326   -0.0128 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4575   -1.2146    2.3868 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9829    1.0612    2.6292 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  2  0
  5  7  1  0
  8  7  1  1
  8  9  1  0
  8 10  1  0
 10 11  1  0
 11 12  1  0
 12 18  1  0
 12 13  1  0
 13 17  2  0
 17 16  1  0
 16 15  1  0
 15 14  2  0
 18  8  1  0
 14 13  1  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
  2 22  1  0
  3 23  1  0
  3 24  1  0
  3 25  1  0
  4 26  1  0
  4 27  1  0
  7 28  1  0
  7 29  1  0
  9 30  1  0
  9 31  1  0
  9 32  1  0
 10 33  1  0
 10 34  1  0
 11 35  1  0
 11 36  1  0
 12 37  1  6
 17 40  1  0
 15 39  1  0
 14 38  1  0
M  END


  Mrv1652309052202392D          

 18 19  0  0  1  0            999 V2000
    1.5229   -3.9884    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2374   -4.4009    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2374   -5.2259    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9519   -3.9884    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6663   -4.4009    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6663   -5.2259    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3808   -3.9884    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0953   -4.4009    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.6103   -5.0683    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4308   -3.6472    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2513   -3.7334    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4228   -4.5404    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.1765   -4.8760    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8910   -4.4635    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5041   -5.0155    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1685   -5.7692    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.3480   -5.6829    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7084   -4.9529    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  2  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  5  7  1  0  0  0  0
  8  7  1  1  0  0  0
  8  9  1  6  0  0  0
  8 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  1  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  1  0  0  0  0
 13 17  2  0  0  0  0
 12 18  1  0  0  0  0
  8 18  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0204880

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)CC(=O)C[C@@]1(C)CC[C@H](O1)C1=COC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C15H22O3/c1-11(2)8-13(16)9-15(3)6-4-14(18-15)12-5-7-17-10-12/h5,7,10-11,14H,4,6,8-9H2,1-3H3/t14-,15+/m0/s1

> <INCHI_KEY>
WOFDWNOSFDVCDF-LSDHHAIUSA-N

> <FORMULA>
C15H22O3

> <MOLECULAR_WEIGHT>
250.338

> <EXACT_MASS>
250.156894568

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
40

> <JCHEM_AVERAGE_POLARIZABILITY>
27.840555030700717

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
1-[(2R,5S)-5-(furan-3-yl)-2-methyloxolan-2-yl]-4-methylpentan-2-one

> <JCHEM_LOGP>
3.271921523333333

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
19.066194418788648

> <JCHEM_PKA_STRONGEST_BASIC>
-2.868678686284605

> <JCHEM_POLAR_SURFACE_AREA>
39.44

> <JCHEM_REFRACTIVITY>
69.76970000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
ngaione (-)

> <JCHEM_VEBER_RULE>
1

$$$$

HEADER    PROTEIN                                 05-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   05-SEP-22         0                                  
HETATM    1  C   UNK     0       2.843  -7.445   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       4.176  -8.215   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       4.176  -9.755   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       5.510  -7.445   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       6.844  -8.215   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       6.844  -9.755   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       8.177  -7.445   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       9.511  -8.215   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       8.606  -9.461   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      10.138  -6.808   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      11.669  -6.969   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      11.989  -8.475   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      13.396  -9.102   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      14.730  -8.332   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      15.874  -9.362   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      15.248 -10.769   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0      13.716 -10.608   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      10.656  -9.245   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8                                                       
CONECT    8    7    9   10   18                                             
CONECT    9    8                                                            
CONECT   10    8   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13   18                                                  
CONECT   13   12   14   17                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   13                                                       
CONECT   18   12    8                                                       
MASTER        0    0    0    0    0    0    0    0   18    0   38    0
END

View in JSmol

Synonyms

Value	Source
Ipomeamarone	MeSH
Ipomeamarone, (2R-cis)-isomer	MeSH
Ipomeamarone, (2S-cis)-isomer	MeSH
Ipomeamarone, (2S-trans)-isomer	MeSH

Chemical Formula

C₁₅H₂₂O₃

Average Mass

250.3380 Da

Monoisotopic Mass

250.15689 Da

IUPAC Name

1-[(2R,5S)-5-(furan-3-yl)-2-methyloxolan-2-yl]-4-methylpentan-2-one

Traditional Name

ngaione (-)

CAS Registry Number

Not Available

SMILES

CC(C)CC(=O)C[C@@]1(C)CC[C@H](O1)C1=COC=C1

InChI Identifier

InChI=1S/C15H22O3/c1-11(2)8-13(16)9-15(3)6-4-14(18-15)12-5-7-17-10-12/h5,7,10-11,14H,4,6,8-9H2,1-3H3/t14-,15+/m0/s1

InChI Key

WOFDWNOSFDVCDF-LSDHHAIUSA-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
Eremophila deserti	LOTUS Database	35616633
Myoporum laetum	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as heteroaromatic compounds. Heteroaromatic compounds are compounds containing an aromatic ring where a carbon atom is linked to an hetero atom.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Heteroaromatic compounds

Sub Class

Not Available

Direct Parent

Heteroaromatic compounds

Alternative Parents

Substituents

Heteroaromatic compound
Tetrahydrofuran
Furan
Ketone
Oxacycle
Ether
Dialkyl ether
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

Furanoid farnesane sesquiterpenoids (LMPR0103020001 )

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	3.27	ChemAxon
pKa (Strongest Acidic)	19.07	ChemAxon
pKa (Strongest Basic)	-2.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	39.44 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	69.77 m³·mol⁻¹	ChemAxon
Polarizability	27.84 Å³	ChemAxon
Number of Rings	2	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

107785

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

120744

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Nemoto H: Synthetic organic chemistry based on small ring compounds. Chem Pharm Bull (Tokyo). 2007 Jul;55(7):961-74. doi: 10.1248/cpb.55.961. [PubMed:17603183 ]
Li Y, Yin Y, Golding JB, Geng S, Chen G, Yang H: Metabolomic and Transcriptomic Analyses of Quality Deterioration in Fusarium solani-Infected Sweet Potato (Ipomoea batatas (L.) Lam cv Xinxiang) Storage Roots. J Agric Food Chem. 2022 Jun 15;70(23):7258-7266. doi: 10.1021/acs.jafc.2c01220. Epub 2022 Jun 7. [PubMed:35702877 ]
Wu J, Pang L, Zhang X, Lu X, Yin L, Lu G, Cheng J: Early Discrimination and Prediction of C. fimbriata-Infected Sweetpotatoes during the Asymptomatic Period Using Electronic Nose. Foods. 2022 Jun 28;11(13):1919. doi: 10.3390/foods11131919. [PubMed:35804741 ]
Dowa Y, Yamada Y, Kato M, Matsumoto N, Kama Y, Shiihara T: Sweet Potato Was Not So Sweet: Undetected Foreign-body Aspiration in a Healthy Child Leading to Acute Bronchial Asthma. Tokai J Exp Clin Med. 2019 Apr 20;44(1):1-4. [PubMed:30963521 ]
Wamalwa LN, Cheseto X, Ouna E, Kaplan F, Maniania NK, Machuka J, Torto B, Ghislain M: Toxic Ipomeamarone accumulation in healthy parts of Sweetpotato (Ipomoea batatas L. Lam) storage roots upon infection by Rhizopus stolonifer. J Agric Food Chem. 2015 Jan 14;63(1):335-42. doi: 10.1021/jf504702z. [PubMed:25418792 ]
LOTUS database [Link]

Showing NP-Card for ngaione (-) (NP0204880)

MOL for NP0204880 (ngaione (-))

3D MOL for NP0204880 (ngaione (-))

3D SDF for NP0204880 (ngaione (-))

3D-SDF for NP0204880 (ngaione (-))

PDB for NP0204880 (ngaione (-))

3D PDB for NP0204880 (ngaione (-))

SMILES for NP0204880 (ngaione (-))

INCHI for NP0204880 (ngaione (-))

Structure for NP0204880 (ngaione (-))

3D Structure for NP0204880 (ngaione (-))