NP-MRD: Showing NP-Card for Holacine (NP0067693)

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Record Information

Version

2.0

Created at

2022-04-28 12:32:04 UTC

Updated at

2022-04-28 12:32:04 UTC

NP-MRD ID

NP0067693

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Holacine

Description

(1R,2S,9S,12S,13R,16S,17R,18R,20S)-16-(dimethylamino)-2,6,7,13,17-pentamethyl-7-azapentacyclo[10.8.0.0²,⁹.0⁵,⁹.0¹³,¹⁸]Icos-5-ene-18,20-diol belongs to the class of organic compounds known as 7-hydroxysteroids. These are steroids carrying a hydroxyl group at the 7-position of the steroid backbone. Holacine is found in Holarrhena antidysenterica . Based on a literature review very few articles have been published on (1R,2S,9S,12S,13R,16S,17R,18R,20S)-16-(dimethylamino)-2,6,7,13,17-pentamethyl-7-azapentacyclo[10.8.0.0²,⁹.0⁵,⁹.0¹³,¹⁸]Icos-5-ene-18,20-diol.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304282214322D          

 30 34  0  0  1  0            999 V2000
    3.6048   -0.3469    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1014    0.3119    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.7791    1.0713    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.9602    1.1719    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.4637    0.5131    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.7860   -0.2463    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6448    0.6137    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.3226    1.3732    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.8191    2.0320    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.6380    1.9314    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4968    2.7915    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5037    1.4738    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0072    0.8150    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.3294    0.0555    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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  7 15  1  1  0  0  0
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  5 25  1  1  0  0  0
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  3 27  1  6  0  0  0
  2 28  1  1  0  0  0
 28 29  1  0  0  0  0
 28 30  1  0  0  0  0
M  END

     RDKit          3D

 74 78  0  0  0  0  0  0  0  0999 V2000
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M  END


  Mrv1652304282214322D          

 30 34  0  0  1  0            999 V2000
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M  END
> <DATABASE_ID>
NP0067693

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@@H]1[C@H](CC[C@]2(C)[C@H]3CC[C@@]45CN(C)C(C)=C4CC[C@@]5(C)[C@@H]3[C@@H](O)C[C@@]12O)N(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C26H44N2O2/c1-16-20(27(5)6)10-12-23(3)19-9-13-25-15-28(7)17(2)18(25)8-11-24(25,4)22(19)21(29)14-26(16,23)30/h16,19-22,29-30H,8-15H2,1-7H3/t16-,19+,20+,21+,22+,23-,24+,25-,26-/m1/s1

> <INCHI_KEY>
FKTUIAROLJADNJ-KSJMQDHVSA-N

> <FORMULA>
C26H44N2O2

> <MOLECULAR_WEIGHT>
416.65

> <EXACT_MASS>
416.340278665

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
74

> <JCHEM_AVERAGE_POLARIZABILITY>
50.514429095724815

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1R,2S,9S,12S,13R,16S,17R,18R,20S)-16-(dimethylamino)-2,6,7,13,17-pentamethyl-7-azapentacyclo[10.8.0.0^{2,9}.0^{5,9}.0^{13,18}]icos-5-ene-18,20-diol

> <ALOGPS_LOGP>
2.65

> <JCHEM_LOGP>
2.1465860606666674

> <ALOGPS_LOGS>
-3.15

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
2

> <JCHEM_PKA>
14.997599232585646

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.991453559075495

> <JCHEM_PKA_STRONGEST_BASIC>
10.081856330703456

> <JCHEM_POLAR_SURFACE_AREA>
46.940000000000005

> <JCHEM_REFRACTIVITY>
124.13049999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.94e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1R,2S,9S,12S,13R,16S,17R,18R,20S)-16-(dimethylamino)-2,6,7,13,17-pentamethyl-7-azapentacyclo[10.8.0.0^{2,9}.0^{5,9}.0^{13,18}]icos-5-ene-18,20-diol

> <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       6.729  -0.648   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       7.656   0.582   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       7.054   2.000   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       5.526   2.188   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       4.599   0.958   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       5.200  -0.460   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       3.070   1.146   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.469   2.563   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       3.396   3.793   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.924   3.605   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       2.794   5.211   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       0.940   2.751   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       0.013   1.521   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       0.615   0.104   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       2.143  -0.084   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -1.443   2.023   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -2.370   0.793   0.000  0.00  0.00           C+0
HETATM   18  N   UNK     0      -1.486  -0.469   0.000  0.00  0.00           N+0
HETATM   19  C   UNK     0      -0.014  -0.018   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -1.988  -1.925   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -3.909   0.820   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -1.416   3.563   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       0.057   4.013   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       1.734   4.071   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       3.672  -0.272   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0       6.453   3.417   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0       7.981   3.230   0.000  0.00  0.00           C+0
HETATM   28  N   UNK     0       9.184   0.394   0.000  0.00  0.00           N+0
HETATM   29  C   UNK     0      10.111   1.624   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       9.786  -1.023   0.000  0.00  0.00           C+0
CONECT    1    2    6                                                       
CONECT    2    1    3   28                                                  
CONECT    3    2    4   27                                                  
CONECT    4    3    5   10   26                                             
CONECT    5    4    6    7   25                                             
CONECT    6    5    1                                                       
CONECT    7    5    8   15                                                  
CONECT    8    7    9   12                                                  
CONECT    9    8   10   11                                                  
CONECT   10    9    4                                                       
CONECT   11    9                                                            
CONECT   12    8   13   23   24                                             
CONECT   13   12   14   16   19                                             
CONECT   14   13   15                                                       
CONECT   15   14    7                                                       
CONECT   16   13   17   22                                                  
CONECT   17   16   18   21                                                  
CONECT   18   17   19   20                                                  
CONECT   19   18   13                                                       
CONECT   20   18                                                            
CONECT   21   17                                                            
CONECT   22   16   23                                                       
CONECT   23   22   12                                                       
CONECT   24   12                                                            
CONECT   25    5                                                            
CONECT   26    4                                                            
CONECT   27    3                                                            
CONECT   28    2   29   30                                                  
CONECT   29   28                                                            
CONECT   30   28                                                            
MASTER        0    0    0    0    0    0    0    0   30    0   68    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₆H₄₄N₂O₂

Average Mass

416.6500 Da

Monoisotopic Mass

416.34028 Da

IUPAC Name

(1R,2S,9S,12S,13R,16S,17R,18R,20S)-16-(dimethylamino)-2,6,7,13,17-pentamethyl-7-azapentacyclo[10.8.0.0^{2,9}.0^{5,9}.0^{13,18}]icos-5-ene-18,20-diol

Traditional Name

(1R,2S,9S,12S,13R,16S,17R,18R,20S)-16-(dimethylamino)-2,6,7,13,17-pentamethyl-7-azapentacyclo[10.8.0.0^{2,9}.0^{5,9}.0^{13,18}]icos-5-ene-18,20-diol

CAS Registry Number

Not Available

SMILES

C[C@@H]1[C@H](CC[C@]2(C)[C@H]3CC[C@@]45CN(C)C(C)=C4CC[C@@]5(C)[C@@H]3[C@@H](O)C[C@@]12O)N(C)C

InChI Identifier

InChI=1S/C26H44N2O2/c1-16-20(27(5)6)10-12-23(3)19-9-13-25-15-28(7)17(2)18(25)8-11-24(25,4)22(19)21(29)14-26(16,23)30/h16,19-22,29-30H,8-15H2,1-7H3/t16-,19+,20+,21+,22+,23-,24+,25-,26-/m1/s1

InChI Key

FKTUIAROLJADNJ-KSJMQDHVSA-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
Holarrhena pubescens	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 7-hydroxysteroids. These are steroids carrying a hydroxyl group at the 7-position of the steroid backbone.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Hydroxysteroids

Direct Parent

7-hydroxysteroids

Alternative Parents

Substituents

7-hydroxysteroid
Tertiary alcohol
Pyrroline
Cyclic alcohol
Tertiary aliphatic amine
Tertiary amine
Secondary alcohol
Azacycle
Organoheterocyclic compound
Enamine
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
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	2.65	ALOGPS
logP	2.15	ChemAxon
logS	-3.2	ALOGPS
pKa (Strongest Acidic)	13.99	ChemAxon
pKa (Strongest Basic)	10.08	ChemAxon
Physiological Charge	2	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	46.94 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	124.13 m³·mol⁻¹	ChemAxon
Polarizability	50.51 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	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

162968899

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Holacine (NP0067693)

MOL for NP0067693 (Holacine)

3D MOL for NP0067693 (Holacine)

3D SDF for NP0067693 (Holacine)

3D-SDF for NP0067693 (Holacine)

PDB for NP0067693 (Holacine)

3D PDB for NP0067693 (Holacine)

SMILES for NP0067693 (Holacine)

INCHI for NP0067693 (Holacine)

Structure for NP0067693 (Holacine)

3D Structure for NP0067693 (Holacine)