NP-MRD: Showing NP-Card for (1'r,2r,2'r,4's,7's,8's,9's,12's,13'r,14'r,16'r)-7',9',13'-trimethyl-5-methylidene-5'-oxaspiro[oxane-2,6'-pentacyclo[10.8.0.0²,⁹.0⁴,⁸.0¹³,¹⁸]icosan]-18'-ene-2',8',14',16'-tetrol (NP0287098)

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Record Information

Version

2.0

Created at

2022-09-09 16:00:08 UTC

Updated at

2022-09-09 16:00:08 UTC

NP-MRD ID

NP0287098

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1'r,2r,2'r,4's,7's,8's,9's,12's,13'r,14'r,16'r)-7',9',13'-trimethyl-5-methylidene-5'-oxaspiro[oxane-2,6'-pentacyclo[10.8.0.0²,⁹.0⁴,⁸.0¹³,¹⁸]icosan]-18'-ene-2',8',14',16'-tetrol

Description

NAMOGENIN C belongs to the class of organic compounds known as 1-hydroxysteroids. These are steroids carrying a hydroxyl group at the 1-position of the steroid backbone. (1'r,2r,2'r,4's,7's,8's,9's,12's,13'r,14'r,16'r)-7',9',13'-trimethyl-5-methylidene-5'-oxaspiro[oxane-2,6'-pentacyclo[10.8.0.0²,⁹.0⁴,⁸.0¹³,¹⁸]icosan]-18'-ene-2',8',14',16'-tetrol is found in Dracaena angustifolia. Based on a literature review very few articles have been published on NAMOGENIN C.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309092218002D          

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M  END

     RDKit          3D

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M  END


  Mrv1652309092218002D          

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 16 23  1  0  0  0  0
 23 24  1  1  0  0  0
 23 25  1  0  0  0  0
 13 25  1  0  0  0  0
 25 26  1  1  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 11 28  1  0  0  0  0
 28 29  1  1  0  0  0
 28 30  1  0  0  0  0
  9 30  1  0  0  0  0
 30 31  1  6  0  0  0
 30 32  1  0  0  0  0
  5 32  1  0  0  0  0
 32 33  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0287098

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@@H]1[C@@]2(CCC(=C)CO2)O[C@H]2C[C@@]3(O)[C@@H]4CC=C5C[C@@H](O)C[C@@H](O)[C@]5(C)[C@H]4CC[C@]3(C)[C@@]12O

> <INCHI_IDENTIFIER>
InChI=1S/C27H40O6/c1-15-7-10-26(32-14-15)16(2)27(31)22(33-26)13-25(30)20-6-5-17-11-18(28)12-21(29)24(17,4)19(20)8-9-23(25,27)3/h5,16,18-22,28-31H,1,6-14H2,2-4H3/t16-,18-,19+,20-,21-,22+,23+,24+,25-,26-,27-/m1/s1

> <INCHI_KEY>
YDCAYRNXFGXGAJ-DETVFNIRSA-N

> <FORMULA>
C27H40O6

> <MOLECULAR_WEIGHT>
460.611

> <EXACT_MASS>
460.282489008

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
73

> <JCHEM_AVERAGE_POLARIZABILITY>
52.17289384237779

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1'R,2R,2'R,4'S,7'S,8'S,9'S,12'S,13'R,14'R,16'R)-7',9',13'-trimethyl-5-methylidene-5'-oxaspiro[oxane-2,6'-pentacyclo[10.8.0.0^{2,9}.0^{4,8}.0^{13,18}]icosan]-18'-ene-2',8',14',16'-tetrol

> <JCHEM_LOGP>
1.5355088349999988

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.981650515277305

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.001056281471271

> <JCHEM_PKA_STRONGEST_BASIC>
-2.750183545956067

> <JCHEM_POLAR_SURFACE_AREA>
99.38000000000001

> <JCHEM_REFRACTIVITY>
123.78209999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(1'R,2R,2'R,4'S,7'S,8'S,9'S,12'S,13'R,14'R,16'R)-7',9',13'-trimethyl-5-methylidene-5'-oxaspiro[oxane-2,6'-pentacyclo[10.8.0.0^{2,9}.0^{4,8}.0^{13,18}]icosan]-18'-ene-2',8',14',16'-tetrol

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 09-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   09-SEP-22         0                                  
HETATM    1  C   UNK     0       8.032  -6.134   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       9.552  -5.884   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      10.095  -4.443   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      11.615  -4.193   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      12.591  -5.384   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0      12.048  -6.825   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0      10.528  -7.075   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0      13.282  -4.008   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0      14.805  -4.240   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      16.173  -3.533   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      17.268  -4.616   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      17.812  -3.175   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0      18.805  -4.526   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      19.497  -3.150   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      21.034  -3.061   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      21.880  -4.347   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      23.418  -4.258   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      24.264  -5.545   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      25.801  -5.455   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0      23.573  -6.921   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      22.035  -7.010   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0      21.344  -8.386   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0      21.189  -5.724   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      20.498  -7.100   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      19.652  -5.813   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      18.960  -7.189   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      17.423  -7.279   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      16.577  -5.992   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      15.746  -7.289   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      15.054  -5.760   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0      14.822  -7.282   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0      13.686  -6.467   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      13.454  -7.989   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    7                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6    8   32                                             
CONECT    6    5    7                                                       
CONECT    7    6    2                                                       
CONECT    8    5    9                                                       
CONECT    9    8   10   30                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12   13   28                                             
CONECT   12   11                                                            
CONECT   13   11   14   25                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17   23                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18   21                                                       
CONECT   21   20   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21   16   24   25                                             
CONECT   24   23                                                            
CONECT   25   23   13   26                                                  
CONECT   26   25   27                                                       
CONECT   27   26   28                                                       
CONECT   28   27   11   29   30                                             
CONECT   29   28                                                            
CONECT   30   28    9   31   32                                             
CONECT   31   30                                                            
CONECT   32   30    5   33                                                  
CONECT   33   32                                                            
MASTER        0    0    0    0    0    0    0    0   33    0   76    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₇H₄₀O₆

Average Mass

460.6110 Da

Monoisotopic Mass

460.28249 Da

IUPAC Name

(1'R,2R,2'R,4'S,7'S,8'S,9'S,12'S,13'R,14'R,16'R)-7',9',13'-trimethyl-5-methylidene-5'-oxaspiro[oxane-2,6'-pentacyclo[10.8.0.0^{2,9}.0^{4,8}.0^{13,18}]icosan]-18'-ene-2',8',14',16'-tetrol

Traditional Name

(1'R,2R,2'R,4'S,7'S,8'S,9'S,12'S,13'R,14'R,16'R)-7',9',13'-trimethyl-5-methylidene-5'-oxaspiro[oxane-2,6'-pentacyclo[10.8.0.0^{2,9}.0^{4,8}.0^{13,18}]icosan]-18'-ene-2',8',14',16'-tetrol

CAS Registry Number

Not Available

SMILES

C[C@@H]1[C@@]2(CCC(=C)CO2)O[C@H]2C[C@@]3(O)[C@@H]4CC=C5C[C@@H](O)C[C@@H](O)[C@]5(C)[C@H]4CC[C@]3(C)[C@@]12O

InChI Identifier

InChI=1S/C27H40O6/c1-15-7-10-26(32-14-15)16(2)27(31)22(33-26)13-25(30)20-6-5-17-11-18(28)12-21(29)24(17,4)19(20)8-9-23(25,27)3/h5,16,18-22,28-31H,1,6-14H2,2-4H3/t16-,18-,19+,20-,21-,22+,23+,24+,25-,26-,27-/m1/s1

InChI Key

YDCAYRNXFGXGAJ-DETVFNIRSA-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
Dracaena angustifolia	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 1-hydroxysteroids. These are steroids carrying a hydroxyl group at the 1-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

1-hydroxysteroids

Alternative Parents

Substituents

3-hydroxy-delta-5-steroid
1-hydroxysteroid
3-hydroxysteroid
17-hydroxysteroid
3-beta-hydroxysteroid
3-beta-hydroxy-delta-5-steroid
14-hydroxysteroid
Delta-5-steroid
Ketal
Monosaccharide
Oxane
Cyclic alcohol
Tetrahydrofuran
Tertiary alcohol
Secondary alcohol
Polyol
Organoheterocyclic compound
Oxacycle
Acetal
Organic oxygen compound
Alcohol
Hydrocarbon derivative
Organooxygen compound
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	1.54	ChemAxon
pKa (Strongest Acidic)	13	ChemAxon
pKa (Strongest Basic)	-2.8	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	99.38 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	123.78 m³·mol⁻¹	ChemAxon
Polarizability	52.17 Å³	ChemAxon
Number of Rings	6	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

9169385

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

10994190

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (1'r,2r,2'r,4's,7's,8's,9's,12's,13'r,14'r,16'r)-7',9',13'-trimethyl-5-methylidene-5'-oxaspiro[oxane-2,6'-pentacyclo[10.8.0.0²,⁹.0⁴,⁸.0¹³,¹⁸]icosan]-18'-ene-2',8',14',16'-tetrol (NP0287098)

MOL for NP0287098 ((1'r,2r,2'r,4's,7's,8's,9's,12's,13'r,14'r,16'r)-7',9',13'-trimethyl-5-methylidene-5'-oxaspiro[oxane-2,6'-pentacyclo[10.8.0.0²,⁹.0⁴,⁸.0¹³,¹⁸]icosan]-18'-ene-2',8',14',16'-tetrol)

3D MOL for NP0287098 ((1'r,2r,2'r,4's,7's,8's,9's,12's,13'r,14'r,16'r)-7',9',13'-trimethyl-5-methylidene-5'-oxaspiro[oxane-2,6'-pentacyclo[10.8.0.0²,⁹.0⁴,⁸.0¹³,¹⁸]icosan]-18'-ene-2',8',14',16'-tetrol)

3D SDF for NP0287098 ((1'r,2r,2'r,4's,7's,8's,9's,12's,13'r,14'r,16'r)-7',9',13'-trimethyl-5-methylidene-5'-oxaspiro[oxane-2,6'-pentacyclo[10.8.0.0²,⁹.0⁴,⁸.0¹³,¹⁸]icosan]-18'-ene-2',8',14',16'-tetrol)

3D-SDF for NP0287098 ((1'r,2r,2'r,4's,7's,8's,9's,12's,13'r,14'r,16'r)-7',9',13'-trimethyl-5-methylidene-5'-oxaspiro[oxane-2,6'-pentacyclo[10.8.0.0²,⁹.0⁴,⁸.0¹³,¹⁸]icosan]-18'-ene-2',8',14',16'-tetrol)

PDB for NP0287098 ((1'r,2r,2'r,4's,7's,8's,9's,12's,13'r,14'r,16'r)-7',9',13'-trimethyl-5-methylidene-5'-oxaspiro[oxane-2,6'-pentacyclo[10.8.0.0²,⁹.0⁴,⁸.0¹³,¹⁸]icosan]-18'-ene-2',8',14',16'-tetrol)

3D PDB for NP0287098 ((1'r,2r,2'r,4's,7's,8's,9's,12's,13'r,14'r,16'r)-7',9',13'-trimethyl-5-methylidene-5'-oxaspiro[oxane-2,6'-pentacyclo[10.8.0.0²,⁹.0⁴,⁸.0¹³,¹⁸]icosan]-18'-ene-2',8',14',16'-tetrol)

SMILES for NP0287098 ((1'r,2r,2'r,4's,7's,8's,9's,12's,13'r,14'r,16'r)-7',9',13'-trimethyl-5-methylidene-5'-oxaspiro[oxane-2,6'-pentacyclo[10.8.0.0²,⁹.0⁴,⁸.0¹³,¹⁸]icosan]-18'-ene-2',8',14',16'-tetrol)

INCHI for NP0287098 ((1'r,2r,2'r,4's,7's,8's,9's,12's,13'r,14'r,16'r)-7',9',13'-trimethyl-5-methylidene-5'-oxaspiro[oxane-2,6'-pentacyclo[10.8.0.0²,⁹.0⁴,⁸.0¹³,¹⁸]icosan]-18'-ene-2',8',14',16'-tetrol)

Structure for NP0287098 ((1'r,2r,2'r,4's,7's,8's,9's,12's,13'r,14'r,16'r)-7',9',13'-trimethyl-5-methylidene-5'-oxaspiro[oxane-2,6'-pentacyclo[10.8.0.0²,⁹.0⁴,⁸.0¹³,¹⁸]icosan]-18'-ene-2',8',14',16'-tetrol)

3D Structure for NP0287098 ((1'r,2r,2'r,4's,7's,8's,9's,12's,13'r,14'r,16'r)-7',9',13'-trimethyl-5-methylidene-5'-oxaspiro[oxane-2,6'-pentacyclo[10.8.0.0²,⁹.0⁴,⁸.0¹³,¹⁸]icosan]-18'-ene-2',8',14',16'-tetrol)