NP-MRD: Showing NP-Card for (+)-22-Hydroxy-24-methylsedn-16-en-24-one-12beta,25beta-olide (NP0080148)

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Record Information

Version

2.0

Created at

2022-04-29 01:12:16 UTC

Updated at

2022-04-29 01:12:17 UTC

NP-MRD ID

NP0080148

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(+)-22-Hydroxy-24-methylsedn-16-en-24-one-12beta,25beta-olide

Description

22-Hydroxy-24-methylsedn-16-en-24-one-12beta,25beta-olide, also known as 22-hmso CPD, belongs to the class of organic compounds known as eudesmanolides, secoeudesmanolides, and derivatives. These are terpenoids with a structure based on the eudesmanolide (a 3,5a,9-trimethyl-naphtho[1,2-b]furan-2-one derivative) or secoeudesmanolide (a 3,6-dimethyl-5-(pentan-2-yl)-1-benzofuran-2-one derivative) skeleton. (+)-22-Hydroxy-24-methylsedn-16-en-24-one-12beta,25beta-olide is found in Lendenfeldia frondosa. (+)-22-Hydroxy-24-methylsedn-16-en-24-one-12beta,25beta-olide was first documented in 2002 (PMID: 12193028). Based on a literature review very few articles have been published on 22-Hydroxy-24-methylsedn-16-en-24-one-12beta,25beta-olide.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304292203122D          

 30 34  0  0  1  0            999 V2000
    3.4717   -0.3806    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9902    0.2611    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    2.8786    1.1591    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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M  END

     RDKit          3D

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M  END


  Mrv1652304292203122D          

 30 34  0  0  1  0            999 V2000
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M  END
> <DATABASE_ID>
NP0080148

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(=O)C1=CC[C@@H]2[C@]3(C)[C@@H](C[C@H]4[C@@]2(C)CC[C@H]2C(C)(C)CCC[C@]42CO)OC(=O)[C@@H]13

> <INCHI_IDENTIFIER>
InChI=1S/C26H38O4/c1-15(28)16-7-8-18-24(4)12-9-17-23(2,3)10-6-11-26(17,14-27)19(24)13-20-25(18,5)21(16)22(29)30-20/h7,17-21,27H,6,8-14H2,1-5H3/t17-,18-,19-,20+,21+,24-,25+,26+/m0/s1

> <INCHI_KEY>
VDBPCCVBAJLGOR-JWZWEURHSA-N

> <FORMULA>
C26H38O4

> <MOLECULAR_WEIGHT>
414.586

> <EXACT_MASS>
414.277009704

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
68

> <JCHEM_AVERAGE_POLARIZABILITY>
47.732105468546685

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1S,2R,5S,10R,11S,13R,16R,20S)-17-acetyl-10-(hydroxymethyl)-2,6,6,20-tetramethyl-14-oxapentacyclo[11.6.1.0^{2,11}.0^{5,10}.0^{16,20}]icos-17-en-15-one

> <ALOGPS_LOGP>
4.71

> <JCHEM_LOGP>
3.931359577333333

> <ALOGPS_LOGS>
-5.07

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
19.772903522011145

> <JCHEM_PKA_STRONGEST_ACIDIC>
19.412976787611477

> <JCHEM_PKA_STRONGEST_BASIC>
-0.868555687171649

> <JCHEM_POLAR_SURFACE_AREA>
63.60000000000001

> <JCHEM_REFRACTIVITY>
116.25079999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.55e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1S,2R,5S,10R,11S,13R,16R,20S)-17-acetyl-10-(hydroxymethyl)-2,6,6,20-tetramethyl-14-oxapentacyclo[11.6.1.0^{2,11}.0^{5,10}.0^{16,20}]icos-17-en-15-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 29-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   29-APR-22         0                                  
HETATM    1  C   UNK     0       6.481  -0.710   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       7.448   0.487   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       6.895   1.925   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       5.373   2.164   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       4.406   0.966   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.959  -0.471   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       3.991  -1.669   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.470  -1.430   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.917   0.007   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.884   1.205   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.331   2.642   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       0.809   2.881   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -0.158   1.683   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       0.395   0.246   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -1.111  -0.808   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -2.550  -0.258   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -2.792   1.263   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -1.597   2.233   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -1.518   3.771   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0      -2.716   4.739   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0      -0.031   4.172   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0      -4.231   1.813   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0      -5.426   0.843   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0      -4.473   3.334   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      -1.246   0.593   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       0.949  -1.191   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       3.852   2.403   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0       4.820   3.601   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0       7.644  -1.719   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       6.295  -2.239   0.000  0.00  0.00           C+0
CONECT    1    2    6   29   30                                             
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6   10   27                                             
CONECT    6    5    1    7                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   14   26                                             
CONECT   10    9    5   11                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13   21                                                  
CONECT   13   12   14   18   25                                             
CONECT   14   13    9   15                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18   22                                                  
CONECT   18   17   13   19                                                  
CONECT   19   18   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19   12                                                       
CONECT   22   17   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22                                                            
CONECT   25   13                                                            
CONECT   26    9                                                            
CONECT   27    5   28                                                       
CONECT   28   27                                                            
CONECT   29    1                                                            
CONECT   30    1                                                            
MASTER        0    0    0    0    0    0    0    0   30    0   68    0
END

View in JSmol

Synonyms

Value	Source
22-Hydroxy-24-methylsedn-16-en-24-one-12b,25b-olide	Generator
22-Hydroxy-24-methylsedn-16-en-24-one-12β,25β-olide	Generator
22-HMSO CPD	MeSH

Chemical Formula

C₂₆H₃₈O₄

Average Mass

414.5860 Da

Monoisotopic Mass

414.27701 Da

IUPAC Name

(1S,2R,5S,10R,11S,13R,16R,20S)-17-acetyl-10-(hydroxymethyl)-2,6,6,20-tetramethyl-14-oxapentacyclo[11.6.1.0^{2,11}.0^{5,10}.0^{16,20}]icos-17-en-15-one

Traditional Name

(1S,2R,5S,10R,11S,13R,16R,20S)-17-acetyl-10-(hydroxymethyl)-2,6,6,20-tetramethyl-14-oxapentacyclo[11.6.1.0^{2,11}.0^{5,10}.0^{16,20}]icos-17-en-15-one

CAS Registry Number

Not Available

SMILES

CC(=O)C1=CC[C@@H]2[C@]3(C)[C@@H](C[C@H]4[C@@]2(C)CC[C@H]2C(C)(C)CCC[C@]42CO)OC(=O)[C@@H]13

InChI Identifier

InChI=1S/C26H38O4/c1-15(28)16-7-8-18-24(4)12-9-17-23(2,3)10-6-11-26(17,14-27)19(24)13-20-25(18,5)21(16)22(29)30-20/h7,17-21,27H,6,8-14H2,1-5H3/t17-,18-,19-,20+,21+,24-,25+,26+/m0/s1

InChI Key

VDBPCCVBAJLGOR-JWZWEURHSA-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
Lendenfeldia frondosa	-	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as eudesmanolides, secoeudesmanolides, and derivatives. These are terpenoids with a structure based on the eudesmanolide (a 3,5a,9-trimethyl-naphtho[1,2-b]furan-2-one derivative) or secoeudesmanolide (a 3,6-dimethyl-5-(pentan-2-yl)-1-benzofuran-2-one derivative) skeleton.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Terpene lactones

Direct Parent

Eudesmanolides, secoeudesmanolides, and derivatives

Alternative Parents

Substituents

Eudesmanolide
Sesquiterpenoid
Naphthofuran
Gamma butyrolactone
Tetrahydrofuran
Carboxylic acid ester
Ketone
Lactone
Monocarboxylic acid or derivatives
Oxacycle
Carboxylic acid derivative
Organoheterocyclic compound
Organooxygen compound
Alcohol
Carbonyl group
Organic oxygen compound
Hydrocarbon derivative
Primary alcohol
Organic oxide
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	4.71	ALOGPS
logP	3.93	ChemAxon
logS	-5.1	ALOGPS
pKa (Strongest Acidic)	19.41	ChemAxon
pKa (Strongest Basic)	-0.87	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	63.6 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	116.25 m³·mol⁻¹	ChemAxon
Polarizability	47.73 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

C00045170

Chemspider ID

552405

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

636667

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Stessman CC, Ebel R, Corvino AJ, Crews P: Employing dereplication and gradient 1D NMR methods to rapidly characterize sponge-derived sesterterpenes. J Nat Prod. 2002 Aug;65(8):1183-6. doi: 10.1021/np010218e. [PubMed:12193028 ]

Showing NP-Card for (+)-22-Hydroxy-24-methylsedn-16-en-24-one-12beta,25beta-olide (NP0080148)

MOL for NP0080148 ((+)-22-Hydroxy-24-methylsedn-16-en-24-one-12beta,25beta-olide)

3D MOL for NP0080148 ((+)-22-Hydroxy-24-methylsedn-16-en-24-one-12beta,25beta-olide)

3D SDF for NP0080148 ((+)-22-Hydroxy-24-methylsedn-16-en-24-one-12beta,25beta-olide)

3D-SDF for NP0080148 ((+)-22-Hydroxy-24-methylsedn-16-en-24-one-12beta,25beta-olide)

PDB for NP0080148 ((+)-22-Hydroxy-24-methylsedn-16-en-24-one-12beta,25beta-olide)

3D PDB for NP0080148 ((+)-22-Hydroxy-24-methylsedn-16-en-24-one-12beta,25beta-olide)

SMILES for NP0080148 ((+)-22-Hydroxy-24-methylsedn-16-en-24-one-12beta,25beta-olide)

INCHI for NP0080148 ((+)-22-Hydroxy-24-methylsedn-16-en-24-one-12beta,25beta-olide)

Structure for NP0080148 ((+)-22-Hydroxy-24-methylsedn-16-en-24-one-12beta,25beta-olide)

3D Structure for NP0080148 ((+)-22-Hydroxy-24-methylsedn-16-en-24-one-12beta,25beta-olide)