NP-MRD: Showing NP-Card for 29-Acetoxyspiroiridal (NP0076030)

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Record Information

Version

1.0

Created at

2022-04-28 21:13:10 UTC

Updated at

2022-04-28 21:13:10 UTC

NP-MRD ID

NP0076030

Secondary Accession Numbers

None

Natural Product Identification

Common Name

29-Acetoxyspiroiridal

Description

CHEMBL123519 belongs to the class of organic compounds known as sesterterpenoids. These are terpenes composed of five consecutive isoprene units. 29-Acetoxyspiroiridal is found in Iris cristata and Iris germanica. Based on a literature review very few articles have been published on CHEMBL123519.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304282223132D          

 38 39  0  0  1  0            999 V2000
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M  END

     RDKit          3D

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M  END


  Mrv1652304282223132D          

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   -4.0046    3.7345    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6721    4.2195    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2510    4.0701    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2633    1.2731    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9308    1.7580    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6845    1.4225    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7707    0.6020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1033    0.1171    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5244    0.2664    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6533   -1.1265    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9824   -0.7392    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
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  1  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  7 10  1  0  0  0  0
  5 11  1  6  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
  4 15  1  1  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
  4 18  1  0  0  0  0
 18 19  1  1  0  0  0
 17 20  1  1  0  0  0
 20 21  2  0  0  0  0
 20 22  1  0  0  0  0
 22 23  2  0  0  0  0
 23 24  1  0  0  0  0
 24 25  2  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  2  0  0  0  0
 28 30  1  0  0  0  0
 25 31  1  0  0  0  0
 31 32  1  0  0  0  0
 32 33  1  0  0  0  0
 33 34  2  0  0  0  0
 34 35  1  0  0  0  0
 34 36  1  0  0  0  0
  3 37  1  1  0  0  0
  3 38  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0076030

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)=CCC\C(COC(C)=O)=C\C=C\C(=C)[C@@H]1CC[C@@]2([C@@H]1O)[C@H](CCCO)\C(CC[C@]2(C)O)=C(\C)C=O

> <INCHI_IDENTIFIER>
InChI=1S/C32H48O6/c1-22(2)10-7-12-26(21-38-25(5)35)13-8-11-23(3)28-16-18-32(30(28)36)29(14-9-19-33)27(24(4)20-34)15-17-31(32,6)37/h8,10-11,13,20,28-30,33,36-37H,3,7,9,12,14-19,21H2,1-2,4-6H3/b11-8+,26-13-,27-24-/t28-,29+,30+,31-,32-/m0/s1

> <INCHI_KEY>
KPFIRSWIEJGVNZ-DDKMFYJYSA-N

> <FORMULA>
C32H48O6

> <MOLECULAR_WEIGHT>
528.73

> <EXACT_MASS>
528.345089266

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
86

> <JCHEM_AVERAGE_POLARIZABILITY>
61.295291387180136

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2Z,4E)-6-[(1R,2S,5S,6S,9Z,10R)-1,6-dihydroxy-10-(3-hydroxypropyl)-6-methyl-9-(1-oxopropan-2-ylidene)spiro[4.5]decan-2-yl]-2-(4-methylpent-3-en-1-yl)hepta-2,4,6-trien-1-yl acetate

> <ALOGPS_LOGP>
4.35

> <JCHEM_LOGP>
3.707543799666667

> <ALOGPS_LOGS>
-5.00

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.782520653131044

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.07239032710287

> <JCHEM_PKA_STRONGEST_BASIC>
-1.9850925507113524

> <JCHEM_POLAR_SURFACE_AREA>
104.06000000000002

> <JCHEM_REFRACTIVITY>
155.49810000000005

> <JCHEM_ROTATABLE_BOND_COUNT>
13

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
5.32e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2Z,4E)-6-[(1R,2S,5S,6S,9Z,10R)-1,6-dihydroxy-10-(3-hydroxypropyl)-6-methyl-9-(1-oxopropan-2-ylidene)spiro[4.5]decan-2-yl]-2-(4-methylpent-3-en-1-yl)hepta-2,4,6-trien-1-yl acetate

> <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       5.450   0.770   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       4.680  -0.564   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       3.140  -0.564   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.370   0.770   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       3.140   2.104   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.680   2.104   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       5.450   3.437   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.680   4.771   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       5.450   6.105   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       6.990   3.437   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.370   3.437   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       3.140   4.771   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       2.370   6.105   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       3.140   7.438   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       1.465  -0.476   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       0.000  -0.000   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -0.000   1.540   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       1.465   2.016   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       1.465   3.556   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0      -1.246   2.445   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -1.085   3.977   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -2.653   1.819   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -3.899   2.724   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      -5.305   2.098   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      -6.551   3.003   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      -6.390   4.534   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0      -7.636   5.440   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0      -7.475   6.971   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0      -8.721   7.876   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0      -6.068   7.598   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      -7.958   2.376   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      -9.204   3.282   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0     -10.611   2.655   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0     -10.772   1.124   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      -9.526   0.219   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0     -12.179   0.497   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0       3.086  -2.103   0.000  0.00  0.00           C+0
HETATM   38  O   UNK     0       1.834  -1.380   0.000  0.00  0.00           O+0
CONECT    1    2    6                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4   37   38                                             
CONECT    4    3    5   15   18                                             
CONECT    5    4    6   11                                                  
CONECT    6    5    1    7                                                  
CONECT    7    6    8   10                                                  
CONECT    8    7    9                                                       
CONECT    9    8                                                            
CONECT   10    7                                                            
CONECT   11    5   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13                                                            
CONECT   15    4   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18   20                                                  
CONECT   18   17    4   19                                                  
CONECT   19   18                                                            
CONECT   20   17   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24   26   31                                                  
CONECT   26   25   27                                                       
CONECT   27   26   28                                                       
CONECT   28   27   29   30                                                  
CONECT   29   28                                                            
CONECT   30   28                                                            
CONECT   31   25   32                                                       
CONECT   32   31   33                                                       
CONECT   33   32   34                                                       
CONECT   34   33   35   36                                                  
CONECT   35   34                                                            
CONECT   36   34                                                            
CONECT   37    3                                                            
CONECT   38    3                                                            
MASTER        0    0    0    0    0    0    0    0   38    0   78    0
END

View in JSmol

Synonyms

Value	Source
29-Acetoxy-26-hydroxy-15,28,16,17-tetradehydro-14,15-dihydrospiroiridal	MeSH

Chemical Formula

C₃₂H₄₈O₆

Average Mass

528.7300 Da

Monoisotopic Mass

528.34509 Da

IUPAC Name

(2Z,4E)-6-[(1R,2S,5S,6S,9Z,10R)-1,6-dihydroxy-10-(3-hydroxypropyl)-6-methyl-9-(1-oxopropan-2-ylidene)spiro[4.5]decan-2-yl]-2-(4-methylpent-3-en-1-yl)hepta-2,4,6-trien-1-yl acetate

Traditional Name

(2Z,4E)-6-[(1R,2S,5S,6S,9Z,10R)-1,6-dihydroxy-10-(3-hydroxypropyl)-6-methyl-9-(1-oxopropan-2-ylidene)spiro[4.5]decan-2-yl]-2-(4-methylpent-3-en-1-yl)hepta-2,4,6-trien-1-yl acetate

CAS Registry Number

Not Available

SMILES

CC(C)=CCC\C(COC(C)=O)=C\C=C\C(=C)[C@@H]1CC[C@@]2([C@@H]1O)[C@H](CCCO)\C(CC[C@]2(C)O)=C(\C)C=O

InChI Identifier

InChI=1S/C32H48O6/c1-22(2)10-7-12-26(21-38-25(5)35)13-8-11-23(3)28-16-18-32(30(28)36)29(14-9-19-33)27(24(4)20-34)15-17-31(32,6)37/h8,10-11,13,20,28-30,33,36-37H,3,7,9,12,14-19,21H2,1-2,4-6H3/b11-8+,26-13-,27-24-/t28-,29+,30+,31-,32-/m0/s1

InChI Key

KPFIRSWIEJGVNZ-DDKMFYJYSA-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
Iris cristata	Plant	KNApSAcK
Iris germanica	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as sesterterpenoids. These are terpenes composed of five consecutive isoprene units.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Sesterterpenoids

Direct Parent

Sesterterpenoids

Alternative Parents

Substituents

Sesterterpenoid
Alpha,beta-unsaturated aldehyde
Cyclic alcohol
Tertiary alcohol
Enal
Carboxylic acid ester
Secondary alcohol
Carboxylic acid derivative
Monocarboxylic acid or derivatives
Primary alcohol
Hydrocarbon derivative
Organic oxide
Alcohol
Carbonyl group
Organic oxygen compound
Aldehyde
Organooxygen compound
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic 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	4.35	ALOGPS
logP	3.71	ChemAxon
logS	-5	ALOGPS
pKa (Strongest Acidic)	14.07	ChemAxon
pKa (Strongest Basic)	-2	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	104.06 Å²	ChemAxon
Rotatable Bond Count	13	ChemAxon
Refractivity	155.5 m³·mol⁻¹	ChemAxon
Polarizability	61.3 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	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

8068831

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

9893161

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for 29-Acetoxyspiroiridal (NP0076030)

MOL for NP0076030 (29-Acetoxyspiroiridal)

3D MOL for NP0076030 (29-Acetoxyspiroiridal)

3D SDF for NP0076030 (29-Acetoxyspiroiridal)

3D-SDF for NP0076030 (29-Acetoxyspiroiridal)

PDB for NP0076030 (29-Acetoxyspiroiridal)

3D PDB for NP0076030 (29-Acetoxyspiroiridal)

SMILES for NP0076030 (29-Acetoxyspiroiridal)

INCHI for NP0076030 (29-Acetoxyspiroiridal)

Structure for NP0076030 (29-Acetoxyspiroiridal)

3D Structure for NP0076030 (29-Acetoxyspiroiridal)