NP-MRD: Showing NP-Card for Fulvine (NP0051161)

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Record Information

Version

2.0

Created at

2022-04-27 22:34:12 UTC

Updated at

2022-04-27 22:34:12 UTC

NP-MRD ID

NP0051161

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Fulvine

Description

Isocromadurine, also known as fulvine, belongs to the class of organic compounds known as pyrrolizines. Pyrrolizines are compounds containing a pyrrolizine moiety, which consists of a pyrrole ring fused to a pyrrolidine ring. Fulvine is found in Crotalaria berteroana, Crotalaria crispata, Crotalaria fulva, Crotalaria madurensis and Crotalaria paniculata. Based on a literature review very few articles have been published on Isocromadurine.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 45 47  0  0  0  0  0  0  0  0999 V2000
   -2.6084   -1.5518    1.0088 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3322   -1.3106   -0.4571 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.0490   -1.8817   -0.9101 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8459   -1.9871   -2.1716 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0190   -2.3269   -0.1198 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5275   -1.7780    1.0218 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8944   -1.1776    0.7973 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9724   -1.7215    0.2711 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0620   -0.7318    0.2677 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6015    0.3466    1.1224 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.8528    1.6369    0.4972 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7833    1.7398   -0.5980 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5851    1.1817    0.1825 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7459    0.4723   -0.6610 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3334    0.8510   -1.3890 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3114    1.0035   -2.6697 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6566    1.1275   -0.7719 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.5624    1.6841    0.6263 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6514    0.0480   -0.9444 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.9645    0.4889   -0.3511 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8907   -0.0634   -2.3386 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1591    0.2153    1.1929 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.4489   -0.6977    1.6587 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6851   -1.8528    1.1923 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0343   -2.4427    1.3484 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1187   -1.9725   -0.9642 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7498   -2.6463    1.7169 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0913   -1.0726    1.5846 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0621   -2.7310   -0.1037 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2904   -0.4088   -0.7561 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9829   -1.1910    0.6930 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7362    2.4385    1.2337 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8312    1.6500    0.0026 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0097    1.0431   -1.4056 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6015    2.7751   -0.9007 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1677    2.0336    0.7130 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0737    2.0033   -1.3691 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1256    2.7079    0.5441 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9451    1.1234    1.3155 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6070    1.8394    0.9682 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1222    1.5460   -0.6137 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7659   -0.1201   -0.8154 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0277    0.3178    0.7400 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1010   -0.9930   -2.5927 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7558    0.3852    2.2045 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  3  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  2  0
 15 17  1  0
 17 18  1  0
 17 19  1  0
 19 20  1  0
 19 21  1  6
 13 22  1  0
 19  2  1  0
 22  7  1  0
 22 10  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  2 26  1  6
  6 27  1  0
  6 28  1  0
  8 29  1  0
  9 30  1  0
  9 31  1  0
 11 32  1  0
 11 33  1  0
 12 34  1  0
 12 35  1  0
 13 36  1  1
 17 37  1  6
 18 38  1  0
 18 39  1  0
 18 40  1  0
 20 41  1  0
 20 42  1  0
 20 43  1  0
 21 44  1  0
 22 45  1  1
M  END


  Mrv1652304282200342D          

 22 24  0  0  1  0            999 V2000
    2.4002   -1.7377    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.6317   -1.4378    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.6794   -0.6141    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4775   -0.4051    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9230   -1.0995    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8194   -1.2069    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5137   -0.7614    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1520   -1.2842    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9501   -1.0751    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8520   -2.0527    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.0273   -2.0302    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1339   -2.9104    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.6111   -3.5486    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.7970   -3.4150    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2742   -4.0532    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5057   -2.6432    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6915   -2.5096    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.5543   -2.7704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1089   -2.0760    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9024   -4.3205    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9222   -2.6672    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7815   -3.4214    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  6  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  1  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  8 10  1  0  0  0  0
 10 11  1  6  0  0  0
 10 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 14 16  1  0  0  0  0
 16 17  1  0  0  0  0
  1 17  1  0  0  0  0
 17 18  1  6  0  0  0
 18 19  1  0  0  0  0
  2 19  1  0  0  0  0
 13 20  1  1  0  0  0
 12 21  1  1  0  0  0
 12 22  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0051161

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@@H]1C(=O)OCC2=CCN3CC[C@@H](OC(=O)[C@H](C)[C@@]1(C)O)[C@@H]23

> <INCHI_IDENTIFIER>
InChI=1S/C16H23NO5/c1-9-14(18)21-8-11-4-6-17-7-5-12(13(11)17)22-15(19)10(2)16(9,3)20/h4,9-10,12-13,20H,5-8H2,1-3H3/t9-,10+,12-,13-,16+/m1/s1

> <INCHI_KEY>
PSUFRPOAICRSTC-ZLGRWFNRSA-N

> <FORMULA>
C16H23NO5

> <MOLECULAR_WEIGHT>
309.362

> <EXACT_MASS>
309.157622845

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
45

> <JCHEM_AVERAGE_POLARIZABILITY>
32.12948880839418

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1R,4R,5S,6S,16R)-5-hydroxy-4,5,6-trimethyl-2,8-dioxa-13-azatricyclo[8.5.1.0^{13,16}]hexadec-10-ene-3,7-dione

> <ALOGPS_LOGP>
0.84

> <JCHEM_LOGP>
0.492990799333333

> <ALOGPS_LOGS>
-0.91

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.049260819773718

> <JCHEM_PKA_STRONGEST_BASIC>
7.081977975373905

> <JCHEM_POLAR_SURFACE_AREA>
76.07000000000001

> <JCHEM_REFRACTIVITY>
79.2258

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.80e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1R,4R,5S,6S,16R)-5-hydroxy-4,5,6-trimethyl-2,8-dioxa-13-azatricyclo[8.5.1.0^{13,16}]hexadec-10-ene-3,7-dione

> <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       4.480  -3.244   0.000  0.00  0.00           C+0
HETATM    2  N   UNK     0       3.046  -2.684   0.000  0.00  0.00           N+0
HETATM    3  C   UNK     0       3.135  -1.146   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       4.625  -0.756   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       5.456  -2.052   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       7.129  -2.253   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       8.426  -1.421   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       9.617  -2.397   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0      11.107  -2.007   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       9.057  -3.832   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       7.518  -3.790   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       9.583  -5.433   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       8.607  -6.624   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       7.088  -6.375   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       6.112  -7.566   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0       6.544  -4.934   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       5.024  -4.684   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       2.901  -5.171   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       2.070  -3.875   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       9.151  -8.065   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      11.055  -4.979   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0      10.792  -6.387   0.000  0.00  0.00           O+0
CONECT    1    2    5   17                                                  
CONECT    2    1    3   19                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    1    6                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10   13   21   22                                             
CONECT   13   12   14   20                                                  
CONECT   14   13   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14   17                                                       
CONECT   17   16    1   18                                                  
CONECT   18   17   19                                                       
CONECT   19   18    2                                                       
CONECT   20   13                                                            
CONECT   21   12                                                            
CONECT   22   12                                                            
MASTER        0    0    0    0    0    0    0    0   22    0   48    0
END

View in JSmol

Synonyms

Value	Source
Fulvine	MeSH
Fulvine, (12xi,13xi)-isomer	MeSH
Fulvine, (14alpha)-isomer	MeSH

Chemical Formula

C₁₆H₂₃NO₅

Average Mass

309.3620 Da

Monoisotopic Mass

309.15762 Da

IUPAC Name

(1R,4R,5S,6S,16R)-5-hydroxy-4,5,6-trimethyl-2,8-dioxa-13-azatricyclo[8.5.1.0^{13,16}]hexadec-10-ene-3,7-dione

Traditional Name

(1R,4R,5S,6S,16R)-5-hydroxy-4,5,6-trimethyl-2,8-dioxa-13-azatricyclo[8.5.1.0^{13,16}]hexadec-10-ene-3,7-dione

CAS Registry Number

Not Available

SMILES

C[C@@H]1C(=O)OCC2=CCN3CC[C@@H](OC(=O)[C@H](C)[C@@]1(C)O)[C@@H]23

InChI Identifier

InChI=1S/C16H23NO5/c1-9-14(18)21-8-11-4-6-17-7-5-12(13(11)17)22-15(19)10(2)16(9,3)20/h4,9-10,12-13,20H,5-8H2,1-3H3/t9-,10+,12-,13-,16+/m1/s1

InChI Key

PSUFRPOAICRSTC-ZLGRWFNRSA-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
Crotalaria berteroana	Plant	KNApSAcK
Crotalaria crispata	Plant	KNApSAcK
Crotalaria fulva	Plant	KNApSAcK
Crotalaria madurensis	Plant	KNApSAcK
Crotalaria paniculata	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as pyrrolizines. Pyrrolizines are compounds containing a pyrrolizine moiety, which consists of a pyrrole ring fused to a pyrrolidine ring.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Pyrrolizines

Sub Class

Not Available

Direct Parent

Pyrrolizines

Alternative Parents

Substituents

Pyrrolizine
Dicarboxylic acid or derivatives
N-alkylpyrrolidine
Pyrrolidine
Pyrroline
Tertiary alcohol
Amino acid or derivatives
Carboxylic acid ester
Lactone
Tertiary amine
Tertiary aliphatic amine
Carboxylic acid derivative
Oxacycle
Azacycle
Organic oxide
Organopnictogen compound
Organic oxygen compound
Organooxygen compound
Organonitrogen compound
Amine
Organic nitrogen compound
Hydrocarbon derivative
Alcohol
Carbonyl group
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

pyrrolizines (CHEBI:5187 )
Pyrrolizidine alkaloids (C10304 )

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	0.84	ALOGPS
logP	0.49	ChemAxon
logS	-0.91	ALOGPS
pKa (Strongest Acidic)	14.05	ChemAxon
pKa (Strongest Basic)	7.08	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	76.07 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	79.23 m³·mol⁻¹	ChemAxon
Polarizability	32.13 Å³	ChemAxon
Number of Rings	3	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

C00002087

Chemspider ID

391074

KEGG Compound ID

C10304

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

442726

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Fulvine (NP0051161)

MOL for NP0051161 (Fulvine)

3D MOL for NP0051161 (Fulvine)

3D SDF for NP0051161 (Fulvine)

3D-SDF for NP0051161 (Fulvine)

PDB for NP0051161 (Fulvine)

3D PDB for NP0051161 (Fulvine)

SMILES for NP0051161 (Fulvine)

INCHI for NP0051161 (Fulvine)

Structure for NP0051161 (Fulvine)

3D Structure for NP0051161 (Fulvine)