NP-MRD: Showing NP-Card for Icaceine (NP0050795)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-04-27 22:07:17 UTC

Updated at

2022-04-27 22:07:18 UTC

NP-MRD ID

NP0050795

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Icaceine

Description

(1R,2R,5R,6R,9S,12S,15R,16S,19R)-6-(dimethylamino)-16-hydroxy-1,5,15-trimethyl-8,13-dioxapentacyclo[10.6.1.0²,¹⁰.0⁵,⁹.0¹⁵,¹⁹]Nonadec-10-en-14-one belongs to the class of organic compounds known as 3-hydroxy delta-7-steroids. These are 3-hydroxy steroids containing a double bond between positions 7 and 8. Icaceine is found in Icacina guesfeldtii and Icacina guessfeldtii. Based on a literature review very few articles have been published on (1R,2R,5R,6R,9S,12S,15R,16S,19R)-6-(dimethylamino)-16-hydroxy-1,5,15-trimethyl-8,13-dioxapentacyclo[10.6.1.0²,¹⁰.0⁵,⁹.0¹⁵,¹⁹]Nonadec-10-en-14-one.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652304282200072D          

 27 31  0  0  1  0            999 V2000
   -0.4627   -0.2794    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6025   -1.0924    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0317   -1.6200    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.8058   -1.3346    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.9456   -0.5215    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.3113    0.0061    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9280   -0.4500    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.4387   -1.0980    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1329   -1.8642    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3165   -1.9825    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.8581   -2.6684    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0640   -2.4444    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5839   -2.9551    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2552   -0.9797    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.5610   -0.2134    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.0503    0.4345    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2338    0.3162    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3842   -0.2675    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.5872   -1.0671    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8894   -1.5073    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9118    0.3668    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.7249    0.2270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6263    1.1408    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9452    0.5167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1977    0.2640    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7082   -1.9849    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3765   -1.3779    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
  4  3  1  1  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  1  6  1  0  0  0  0
  5  7  1  0  0  0  0
  7  8  1  1  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
  4 10  1  0  0  0  0
 10 11  1  6  0  0  0
 11 12  1  0  0  0  0
  3 12  1  0  0  0  0
 12 13  2  0  0  0  0
  8 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
  7 17  1  0  0  0  0
 15 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 14 20  1  1  0  0  0
 18 21  1  1  0  0  0
 21 22  1  0  0  0  0
 21 23  1  0  0  0  0
 15 24  1  1  0  0  0
  5 25  1  1  0  0  0
  3 26  1  6  0  0  0
  2 27  1  1  0  0  0
M  END


  Mrv1652304282200072D          

 27 31  0  0  1  0            999 V2000
   -0.4627   -0.2794    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6025   -1.0924    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0317   -1.6200    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.8058   -1.3346    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.9456   -0.5215    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.3113    0.0061    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9280   -0.4500    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.4387   -1.0980    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1329   -1.8642    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3165   -1.9825    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.8581   -2.6684    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0640   -2.4444    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5839   -2.9551    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2552   -0.9797    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.5610   -0.2134    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.0503    0.4345    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2338    0.3162    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3842   -0.2675    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.5872   -1.0671    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8894   -1.5073    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9118    0.3668    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.7249    0.2270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6263    1.1408    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9452    0.5167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1977    0.2640    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7082   -1.9849    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3765   -1.3779    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
  4  3  1  1  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  1  6  1  0  0  0  0
  5  7  1  0  0  0  0
  7  8  1  1  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
  4 10  1  0  0  0  0
 10 11  1  6  0  0  0
 11 12  1  0  0  0  0
  3 12  1  0  0  0  0
 12 13  2  0  0  0  0
  8 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
  7 17  1  0  0  0  0
 15 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 14 20  1  1  0  0  0
 18 21  1  1  0  0  0
 21 22  1  0  0  0  0
 21 23  1  0  0  0  0
 15 24  1  1  0  0  0
  5 25  1  1  0  0  0
  3 26  1  6  0  0  0
  2 27  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0050795

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CN(C)[C@H]1CO[C@H]2C3=C[C@@H]4OC(=O)[C@]5(C)[C@H]4[C@](C)(CC[C@@H]5O)[C@H]3CC[C@]12C

> <INCHI_IDENTIFIER>
InChI=1S/C22H33NO4/c1-20-9-7-16(24)22(3)17(20)14(27-19(22)25)10-12-13(20)6-8-21(2)15(23(4)5)11-26-18(12)21/h10,13-18,24H,6-9,11H2,1-5H3/t13-,14-,15-,16-,17+,18-,20+,21+,22-/m0/s1

> <INCHI_KEY>
MRVMMDQTZLIFLF-ABDBSVHKSA-N

> <FORMULA>
C22H33NO4

> <MOLECULAR_WEIGHT>
375.509

> <EXACT_MASS>
375.240958547

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
60

> <JCHEM_AVERAGE_POLARIZABILITY>
42.487820419492266

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1R,2R,5R,6R,9S,12S,15R,16S,19R)-6-(dimethylamino)-16-hydroxy-1,5,15-trimethyl-8,13-dioxapentacyclo[10.6.1.0^{2,10}.0^{5,9}.0^{15,19}]nonadec-10-en-14-one

> <ALOGPS_LOGP>
2.72

> <JCHEM_LOGP>
2.0918470219999996

> <ALOGPS_LOGS>
-2.88

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.44860284070856

> <JCHEM_PKA_STRONGEST_BASIC>
8.996511343169749

> <JCHEM_POLAR_SURFACE_AREA>
59.0

> <JCHEM_REFRACTIVITY>
102.46689999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.00e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1R,2R,5R,6R,9S,12S,15R,16S,19R)-6-(dimethylamino)-16-hydroxy-1,5,15-trimethyl-8,13-dioxapentacyclo[10.6.1.0^{2,10}.0^{5,9}.0^{15,19}]nonadec-10-en-14-one

> <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      -0.864  -0.521   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.125  -2.039   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.059  -3.024   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.504  -2.491   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.765  -0.973   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.581   0.011   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       3.599  -0.840   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.552  -2.050   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       3.981  -3.480   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.457  -3.701   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       1.602  -4.981   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       0.120  -4.563   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0      -1.090  -5.516   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       6.076  -1.829   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       6.647  -0.398   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       5.694   0.811   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       4.170   0.590   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       8.184  -0.499   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       8.563  -1.992   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       7.260  -2.814   0.000  0.00  0.00           O+0
HETATM   21  N   UNK     0       9.169   0.685   0.000  0.00  0.00           N+0
HETATM   22  C   UNK     0      10.686   0.424   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       8.636   2.130   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       7.364   0.964   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       2.236   0.493   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      -1.322  -3.705   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0      -2.570  -2.572   0.000  0.00  0.00           O+0
CONECT    1    2    6                                                       
CONECT    2    1    3   27                                                  
CONECT    3    2    4   12   26                                             
CONECT    4    3    5   10                                                  
CONECT    5    4    6    7   25                                             
CONECT    6    5    1                                                       
CONECT    7    5    8   17                                                  
CONECT    8    7    9   14                                                  
CONECT    9    8   10                                                       
CONECT   10    9    4   11                                                  
CONECT   11   10   12                                                       
CONECT   12   11    3   13                                                  
CONECT   13   12                                                            
CONECT   14    8   15   20                                                  
CONECT   15   14   16   18   24                                             
CONECT   16   15   17                                                       
CONECT   17   16    7                                                       
CONECT   18   15   19   21                                                  
CONECT   19   18   20                                                       
CONECT   20   19   14                                                       
CONECT   21   18   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21                                                            
CONECT   24   15                                                            
CONECT   25    5                                                            
CONECT   26    3                                                            
CONECT   27    2                                                            
MASTER        0    0    0    0    0    0    0    0   27    0   62    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₂H₃₃NO₄

Average Mass

375.5090 Da

Monoisotopic Mass

375.24096 Da

IUPAC Name

(1R,2R,5R,6R,9S,12S,15R,16S,19R)-6-(dimethylamino)-16-hydroxy-1,5,15-trimethyl-8,13-dioxapentacyclo[10.6.1.0^{2,10}.0^{5,9}.0^{15,19}]nonadec-10-en-14-one

Traditional Name

(1R,2R,5R,6R,9S,12S,15R,16S,19R)-6-(dimethylamino)-16-hydroxy-1,5,15-trimethyl-8,13-dioxapentacyclo[10.6.1.0^{2,10}.0^{5,9}.0^{15,19}]nonadec-10-en-14-one

CAS Registry Number

Not Available

SMILES

CN(C)[C@H]1CO[C@H]2C3=C[C@@H]4OC(=O)[C@]5(C)[C@H]4[C@](C)(CC[C@@H]5O)[C@H]3CC[C@]12C

InChI Identifier

InChI=1S/C22H33NO4/c1-20-9-7-16(24)22(3)17(20)14(27-19(22)25)10-12-13(20)6-8-21(2)15(23(4)5)11-26-18(12)21/h10,13-18,24H,6-9,11H2,1-5H3/t13-,14-,15-,16-,17+,18-,20+,21+,22-/m0/s1

InChI Key

MRVMMDQTZLIFLF-ABDBSVHKSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Icacina guesfeldtii	Plant	KNApSAcK
Icacina guessfeldtii	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 3-hydroxy delta-7-steroids. These are 3-hydroxy steroids containing a double bond between positions 7 and 8.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Hydroxysteroids

Direct Parent

3-hydroxy delta-7-steroids

Alternative Parents

Substituents

3-hydroxy-delta-7-steroid
15-oxasteroid
Delta-7-steroid
Naphthofuran
Gamma butyrolactone
Tetrahydrofuran
Cyclic alcohol
Tertiary aliphatic amine
Tertiary amine
Secondary alcohol
Lactone
Carboxylic acid ester
Amino acid or derivatives
Oxacycle
Organoheterocyclic compound
Monocarboxylic acid or derivatives
Ether
Dialkyl ether
Carboxylic acid derivative
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
Carbonyl group
Amine
Alcohol
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	2.72	ALOGPS
logP	2.09	ChemAxon
logS	-2.9	ALOGPS
pKa (Strongest Acidic)	14.45	ChemAxon
pKa (Strongest Basic)	9	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	59 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	102.47 m³·mol⁻¹	ChemAxon
Polarizability	42.49 Å³	ChemAxon
Number of Rings	5	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

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

163059169

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Icaceine (NP0050795)

MOL for NP0050795 (Icaceine)

3D MOL for NP0050795 (Icaceine)

3D SDF for NP0050795 (Icaceine)

3D-SDF for NP0050795 (Icaceine)

PDB for NP0050795 (Icaceine)

3D PDB for NP0050795 (Icaceine)

SMILES for NP0050795 (Icaceine)

INCHI for NP0050795 (Icaceine)

Structure for NP0050795 (Icaceine)

3D Structure for NP0050795 (Icaceine)