NP-MRD: Showing NP-Card for CIF 2 (NP0084963)

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Record Information

Version

2.0

Created at

2022-04-29 05:34:04 UTC

Updated at

2022-04-29 05:34:04 UTC

NP-MRD ID

NP0084963

Secondary Accession Numbers

None

Natural Product Identification

Common Name

CIF 2

Description

Alkhanol, also known as isoerivanin, belongs to the class of organic compounds known as eudesmanolides, secoeudesmanolides, and derivatives. These are terpenoids with a structure based on the eudesmanolide (a 3,5a,9-trimethyl-naphtho[1,2-b]furan-2-one derivative) or secoeudesmanolide (a 3,6-dimethyl-5-(pentan-2-yl)-1-benzofuran-2-one derivative) skeleton. Alkhanol is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, Alkhanol has been detected, but not quantified in, herbs and spices and tea. CIF 2 is found in Brassica oleracea cv. botrytis . This could make alkhanol a potential biomarker for the consumption of these foods.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 35 38  0  0  0  0  0  0  0  0999 V2000
    2.9875    0.7187   -2.1310 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1162    0.3799   -1.7032 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0355   -0.0855   -2.6272 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5062    0.4518   -0.2870 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4690    0.9490    0.5682 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.2213    0.2882    0.6772 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0543   -0.7584   -0.0082 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1340    0.8209    1.5821 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.6507    0.8536    3.0032 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6912   -0.9940    3.1969 S   0  0  0  0  0  0  0  0  0  0  0  0
    0.1561   -1.1982    2.2621 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7650   -2.1840    2.2798 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8792   -2.1038    1.4970 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0721   -1.0102    0.6794 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0566   -0.6114   -0.2188 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2325   -1.2231   -0.6041 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0512   -0.6130   -1.5269 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6689    0.6062   -2.0464 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4961    1.2100   -1.6582 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6582    0.6254   -0.7388 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4756    0.9671   -0.1786 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0692    0.0254    0.6832 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0486   -0.1095    1.5021 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.7358   -0.8211   -3.2495 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8512   -0.5631    0.0052 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4173    1.0976   -0.1339 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6177    1.8084    1.1252 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8226    1.8299    1.2439 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9003    1.2906    3.6598 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6475    1.2651    3.0938 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6341   -2.8659    1.4824 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4700   -2.1792   -0.1558 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9550   -1.0845   -1.8221 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3471    1.0604   -2.7785 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2322    2.1566   -2.0832 H   0  0  0  0  0  0  0  0  0  0  0  0
  3  2  1  0
  2  1  2  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  6  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 22  1  0
 22 21  2  0
 21 20  1  0
 20 19  2  0
 19 18  1  0
 18 17  2  0
 17 16  1  0
 16 15  2  0
 22 23  1  0
 23  8  1  0
 23 11  1  0
 15 14  1  0
 15 20  1  0
  3 24  1  0
  4 25  1  0
  4 26  1  0
  5 27  1  0
  8 28  1  6
  9 29  1  0
  9 30  1  0
 13 31  1  0
 19 35  1  0
 18 34  1  0
 17 33  1  0
 16 32  1  0
M  END


  Mrv0541 02241212042D          

 23 26  0  0  0  0            999 V2000
   -2.3941    2.5566    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5937    1.7553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0004    1.1812    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2087    1.4111    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0091    2.2124    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6010    2.7838    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5079    0.9734    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.1212    1.5047    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1858    2.2661    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9348    1.3891    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.4387    2.0362    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1303    2.7947    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.3166    2.9076    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3919    0.7089    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1780    0.9348    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2070    1.7553    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    1.1082   -0.0675    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6383   -0.7008    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.2945   -0.2092    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3546   -1.4759    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7677   -2.1918    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3546   -2.9076    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5937   -2.1918    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  1  6  1  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
  4  7  1  0  0  0  0
  5  6  2  0  0  0  0
  5  9  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  8 10  1  0  0  0  0
  9 13  2  0  0  0  0
 10 11  1  0  0  0  0
 10 14  1  0  0  0  0
 11 12  2  0  0  0  0
 11 16  1  0  0  0  0
 12 13  1  0  0  0  0
 14 15  1  0  0  0  0
 14 17  1  0  0  0  0
 15 16  1  0  0  0  0
 17 18  1  0  0  0  0
 17 19  2  0  0  0  0
 18 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  2  0  0  0  0
 21 23  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0084963

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC(=O)CNC(=O)C1CSC2=NC=C3C(=NC4=CC=CC=C34)N12

> <INCHI_IDENTIFIER>
InChI=1S/C15H12N4O3S/c20-12(21)6-16-14(22)11-7-23-15-17-5-9-8-3-1-2-4-10(8)18-13(9)19(11)15/h1-5,11H,6-7H2,(H,16,22)(H,20,21)

> <INCHI_KEY>
ZPXJZOIRMZYIAP-UHFFFAOYSA-N

> <FORMULA>
C15H12N4O3S

> <MOLECULAR_WEIGHT>
328.346

> <EXACT_MASS>
328.06301096

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_AVERAGE_POLARIZABILITY>
31.902666963310438

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-{5-thia-2,7,16-triazatetracyclo[7.7.0.0²,⁶.0¹⁰,¹⁵]hexadeca-1(16),6,8,10,12,14-hexaen-3-ylformamido}acetic acid

> <ALOGPS_LOGP>
0.89

> <JCHEM_LOGP>
0.9362612703156815

> <ALOGPS_LOGS>
-3.39

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
13.751012104627712

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.5039401348175527

> <JCHEM_PKA_STRONGEST_BASIC>
1.803026156280384

> <JCHEM_POLAR_SURFACE_AREA>
97.11

> <JCHEM_REFRACTIVITY>
83.21089999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.33e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
{5-thia-2,7,16-triazatetracyclo[7.7.0.0²,⁶.0¹⁰,¹⁵]hexadeca-1(16),6,8,10,12,14-hexaen-3-ylformamido}acetic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  C   UNK     0      -4.469   4.772   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -4.842   3.277   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -3.734   2.205   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -2.256   2.634   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -1.884   4.130   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -2.989   5.196   0.000  0.00  0.00           C+0
HETATM    7  N   UNK     0      -0.948   1.817   0.000  0.00  0.00           N+0
HETATM    8  C   UNK     0       0.226   2.809   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -0.347   4.230   0.000  0.00  0.00           C+0
HETATM   10  N   UNK     0       1.745   2.593   0.000  0.00  0.00           N+0
HETATM   11  C   UNK     0       2.686   3.801   0.000  0.00  0.00           C+0
HETATM   12  N   UNK     0       2.110   5.217   0.000  0.00  0.00           N+0
HETATM   13  C   UNK     0       0.591   5.428   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.598   1.323   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.066   1.745   0.000  0.00  0.00           C+0
HETATM   16  S   UNK     0       4.120   3.277   0.000  0.00  0.00           S+0
HETATM   17  C   UNK     0       2.069  -0.126   0.000  0.00  0.00           C+0
HETATM   18  N   UNK     0       3.058  -1.308   0.000  0.00  0.00           N+0
HETATM   19  O   UNK     0       0.550  -0.391   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       2.529  -2.755   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       3.300  -4.091   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       2.529  -5.428   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0       4.842  -4.091   0.000  0.00  0.00           O+0
CONECT    1    2    6                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5    7                                                  
CONECT    5    4    6    9                                                  
CONECT    6    1    5                                                       
CONECT    7    4    8                                                       
CONECT    8    7    9   10                                                  
CONECT    9    5    8   13                                                  
CONECT   10    8   11   14                                                  
CONECT   11   10   12   16                                                  
CONECT   12   11   13                                                       
CONECT   13    9   12                                                       
CONECT   14   10   15   17                                                  
CONECT   15   14   16                                                       
CONECT   16   11   15                                                       
CONECT   17   14   18   19                                                  
CONECT   18   17   20                                                       
CONECT   19   17                                                            
CONECT   20   18   21                                                       
CONECT   21   20   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21                                                            
MASTER        0    0    0    0    0    0    0    0   23    0   52    0
END

View in JSmol

Synonyms

Value	Source
Alhanol	HMDB
Alkanol	HMDB
Isoerivanin	HMDB
[3S-(3alpha,3Aalpha,5abeta,6alpha,8alpha,9bbeta)]-3a,4,5,5a,6,7,8,9b-octahydro-6,8-dihydroxy-3,5a,9-trimethylnaphtho[1,2-b]furan-2(3H)-one	HMDB
2-{[hydroxy({5-thia-2,7,16-triazatetracyclo[7.7.0.0²,⁶.0¹⁰,¹⁵]hexadeca-1(16),6,8,10,12,14-hexaen-3-yl})methylidene]amino}acetate	Generator

Chemical Formula

C₁₅H₁₂N₄O₃S

Average Mass

328.3460 Da

Monoisotopic Mass

328.06301 Da

IUPAC Name

2-{5-thia-2,7,16-triazatetracyclo[7.7.0.0²,⁶.0¹⁰,¹⁵]hexadeca-1(16),6,8,10,12,14-hexaen-3-ylformamido}acetic acid

Traditional Name

{5-thia-2,7,16-triazatetracyclo[7.7.0.0²,⁶.0¹⁰,¹⁵]hexadeca-1(16),6,8,10,12,14-hexaen-3-ylformamido}acetic acid

CAS Registry Number

Not Available

SMILES

OC(=O)CNC(=O)C1CSC2=NC=C3C(=NC4=CC=CC=C34)N12

InChI Identifier

InChI=1S/C15H12N4O3S/c20-12(21)6-16-14(22)11-7-23-15-17-5-9-8-3-1-2-4-10(8)18-13(9)19(11)15/h1-5,11H,6-7H2,(H,16,22)(H,20,21)

InChI Key

ZPXJZOIRMZYIAP-UHFFFAOYSA-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
Brassica oleracea cv. botrytis	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as eudesmanolides, secoeudesmanolides, and derivatives. These are terpenoids with a structure based on the eudesmanolide (a 3,5a,9-trimethyl-naphtho[1,2-b]furan-2-one derivative) or secoeudesmanolide (a 3,6-dimethyl-5-(pentan-2-yl)-1-benzofuran-2-one derivative) skeleton.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Terpene lactones

Direct Parent

Eudesmanolides, secoeudesmanolides, and derivatives

Alternative Parents

Substituents

Eudesmanolide
Sesquiterpenoid
Naphthofuran
Gamma butyrolactone
Tetrahydrofuran
Secondary alcohol
Lactone
Carboxylic acid ester
Oxacycle
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Organoheterocyclic compound
Alcohol
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Carbonyl group
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic 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	0.89	ALOGPS
logP	0.94	ChemAxon
logS	-3.4	ALOGPS
pKa (Strongest Acidic)	3.5	ChemAxon
pKa (Strongest Basic)	1.8	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	97.11 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	83.21 m³·mol⁻¹	ChemAxon
Polarizability	31.9 Å³	ChemAxon
Number of Rings	4	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

HMDB0036152

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB015003

KNApSAcK ID

C00013000

Chemspider ID

10424698

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

13944248

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Showing NP-Card for CIF 2 (NP0084963)

MOL for NP0084963 (CIF 2)

3D MOL for NP0084963 (CIF 2)

3D SDF for NP0084963 (CIF 2)

3D-SDF for NP0084963 (CIF 2)

PDB for NP0084963 (CIF 2)

3D PDB for NP0084963 (CIF 2)

SMILES for NP0084963 (CIF 2)

INCHI for NP0084963 (CIF 2)

Structure for NP0084963 (CIF 2)

3D Structure for NP0084963 (CIF 2)