NP-MRD: Showing NP-Card for 4-ethenyl-21,24-dihydroxy-10-methyl-15,23-dioxa-25-azaheptacyclo[19.2.2.2¹⁶,¹⁹.1³,⁷.0¹,²².0⁸,¹³.0¹⁴,²⁸]octacosa-5,16,18,24,26-pentaen-2-one (NP0309180)

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Record Information

Version

1.0

Created at

2022-09-11 03:35:06 UTC

Updated at

2022-09-11 03:35:06 UTC

NP-MRD ID

NP0309180

Secondary Accession Numbers

None

Natural Product Identification

Common Name

4-ethenyl-21,24-dihydroxy-10-methyl-15,23-dioxa-25-azaheptacyclo[19.2.2.2¹⁶,¹⁹.1³,⁷.0¹,²².0⁸,¹³.0¹⁴,²⁸]octacosa-5,16,18,24,26-pentaen-2-one

Description

Hirsutellone C belongs to the class of organic compounds known as prostaglandins and related compounds. These are unsaturated carboxylic acids consisting of a 20 carbon skeleton that also contains a five member ring, and are based upon the fatty acid arachidonic acid. 4-ethenyl-21,24-dihydroxy-10-methyl-15,23-dioxa-25-azaheptacyclo[19.2.2.2¹⁶,¹⁹.1³,⁷.0¹,²².0⁸,¹³.0¹⁴,²⁸]octacosa-5,16,18,24,26-pentaen-2-one is found in Hirsutella nivea. It was first documented in 2011 (PMID: 21913732). Based on a literature review very few articles have been published on Hirsutellone C.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309112205352D          

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M  END

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  Mrv1652309112205352D          

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M  END
> <DATABASE_ID>
NP0309180

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1CCC2C(C1)C1C=CC(C=C)C3C1C2OC1=CC=C(CC2(O)N=C(O)C4(OC24)C3=O)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C28H31NO5/c1-3-16-7-11-18-20-12-14(2)4-10-19(20)23-22(18)21(16)24(30)28-25(34-28)27(32,29-26(28)31)13-15-5-8-17(33-23)9-6-15/h3,5-9,11,14,16,18-23,25,32H,1,4,10,12-13H2,2H3,(H,29,31)

> <INCHI_KEY>
IACNHKNLBOBPTL-UHFFFAOYSA-N

> <FORMULA>
C28H31NO5

> <MOLECULAR_WEIGHT>
461.558

> <EXACT_MASS>
461.220223102

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
65

> <JCHEM_AVERAGE_POLARIZABILITY>
48.893981798111966

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
4-ethenyl-21,24-dihydroxy-10-methyl-15,23-dioxa-25-azaheptacyclo[19.2.2.2^{16,19}.1^{3,7}.0^{1,22}.0^{8,13}.0^{14,28}]octacosa-5,16,18,24,26-pentaen-2-one

> <JCHEM_LOGP>
4.760629619

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
7

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
11.738450297660384

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.8789441700387712

> <JCHEM_PKA_STRONGEST_BASIC>
-2.443383916432516

> <JCHEM_POLAR_SURFACE_AREA>
91.65

> <JCHEM_REFRACTIVITY>
126.35279999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
4-ethenyl-21,24-dihydroxy-10-methyl-15,23-dioxa-25-azaheptacyclo[19.2.2.2^{16,19}.1^{3,7}.0^{1,22}.0^{8,13}.0^{14,28}]octacosa-5,16,18,24,26-pentaen-2-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 11-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   11-SEP-22         0                                  
HETATM    1  C   UNK     0       4.902  -8.790   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       4.808  -7.253   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       3.430  -6.566   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.159  -7.450   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.758  -6.786   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.606  -5.224   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -0.685  -4.313   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -2.183  -4.672   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -3.242  -3.554   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -4.740  -3.913   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -2.804  -2.078   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -1.307  -1.719   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -0.247  -2.837   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       1.310  -2.808   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       1.193  -1.184   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       2.056   0.174   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       3.024  -1.038   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       4.547  -0.899   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       5.273   0.453   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       4.300   1.698   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       2.761   1.578   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       6.685  -0.368   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       7.504  -1.792   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       8.743  -0.877   0.000  0.00  0.00           O+0
HETATM   25  N   UNK     0       8.587  -2.953   0.000  0.00  0.00           N+0
HETATM   26  C   UNK     0       7.946  -4.381   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0       8.702  -5.723   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0       6.402  -4.190   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0       7.634  -3.267   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0       6.218  -2.661   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       4.980  -4.912   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0       5.384  -6.398   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0       3.371  -5.010   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       1.882  -4.312   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   33                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7   34                                                  
CONECT    7    6    8   13                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12    7   14                                                  
CONECT   14   13   15   34                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17   21                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20   22                                                  
CONECT   20   19   21                                                       
CONECT   21   20   16                                                       
CONECT   22   19   23                                                       
CONECT   23   22   24   25   30                                             
CONECT   24   23                                                            
CONECT   25   23   26                                                       
CONECT   26   25   27   28                                                  
CONECT   27   26                                                            
CONECT   28   26   29   30   31                                             
CONECT   29   28   30                                                       
CONECT   30   29   23   28                                                  
CONECT   31   28   32   33                                                  
CONECT   32   31                                                            
CONECT   33   31    3   34                                                  
CONECT   34   33    6   14                                                  
MASTER        0    0    0    0    0    0    0    0   34    0   80    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₈H₃₁NO₅

Average Mass

461.5580 Da

Monoisotopic Mass

461.22022 Da

IUPAC Name

4-ethenyl-21,24-dihydroxy-10-methyl-15,23-dioxa-25-azaheptacyclo[19.2.2.2^{16,19}.1^{3,7}.0^{1,22}.0^{8,13}.0^{14,28}]octacosa-5,16,18,24,26-pentaen-2-one

Traditional Name

4-ethenyl-21,24-dihydroxy-10-methyl-15,23-dioxa-25-azaheptacyclo[19.2.2.2^{16,19}.1^{3,7}.0^{1,22}.0^{8,13}.0^{14,28}]octacosa-5,16,18,24,26-pentaen-2-one

CAS Registry Number

Not Available

SMILES

CC1CCC2C(C1)C1C=CC(C=C)C3C1C2OC1=CC=C(CC2(O)N=C(O)C4(OC24)C3=O)C=C1

InChI Identifier

InChI=1S/C28H31NO5/c1-3-16-7-11-18-20-12-14(2)4-10-19(20)23-22(18)21(16)24(30)28-25(34-28)27(32,29-26(28)31)13-15-5-8-17(33-23)9-6-15/h3,5-9,11,14,16,18-23,25,32H,1,4,10,12-13H2,2H3,(H,29,31)

InChI Key

IACNHKNLBOBPTL-UHFFFAOYSA-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
Hirsutella nivea	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as prostaglandins and related compounds. These are unsaturated carboxylic acids consisting of a 20 carbon skeleton that also contains a five member ring, and are based upon the fatty acid arachidonic acid.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Eicosanoids

Direct Parent

Prostaglandins and related compounds

Alternative Parents

Substituents

Prostaglandin skeleton
Macrolactam
Alkyl aryl ether
Morpholine
Oxazinane
Benzenoid
2-pyrrolidone
Pyrrolidone
Pyrrolidine
Carboxamide group
Ketone
Lactam
Secondary carboxylic acid amide
Alkanolamine
Carboxylic acid derivative
Dialkyl ether
Oxirane
Ether
Oxacycle
Azacycle
Organoheterocyclic compound
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organic nitrogen compound
Organonitrogen compound
Organooxygen compound
Carbonyl group
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic 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	4.76	ChemAxon
pKa (Strongest Acidic)	1.88	ChemAxon
pKa (Strongest Basic)	-2.4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	91.65 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	126.35 m³·mol⁻¹	ChemAxon
Polarizability	48.89 Å³	ChemAxon
Number of Rings	7	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

20559441

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

16727716

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Nicolaou KC, Sun YP, Sarlah D, Zhan W, Wu TR: Bioinspired synthesis of hirsutellones A, B, and C. Org Lett. 2011 Oct 21;13(20):5708-10. doi: 10.1021/ol202239u. Epub 2011 Sep 14. [PubMed:21913732 ]
LOTUS database [Link]

Showing NP-Card for 4-ethenyl-21,24-dihydroxy-10-methyl-15,23-dioxa-25-azaheptacyclo[19.2.2.2¹⁶,¹⁹.1³,⁷.0¹,²².0⁸,¹³.0¹⁴,²⁸]octacosa-5,16,18,24,26-pentaen-2-one (NP0309180)

MOL for NP0309180 (4-ethenyl-21,24-dihydroxy-10-methyl-15,23-dioxa-25-azaheptacyclo[19.2.2.2¹⁶,¹⁹.1³,⁷.0¹,²².0⁸,¹³.0¹⁴,²⁸]octacosa-5,16,18,24,26-pentaen-2-one)

3D MOL for NP0309180 (4-ethenyl-21,24-dihydroxy-10-methyl-15,23-dioxa-25-azaheptacyclo[19.2.2.2¹⁶,¹⁹.1³,⁷.0¹,²².0⁸,¹³.0¹⁴,²⁸]octacosa-5,16,18,24,26-pentaen-2-one)

3D SDF for NP0309180 (4-ethenyl-21,24-dihydroxy-10-methyl-15,23-dioxa-25-azaheptacyclo[19.2.2.2¹⁶,¹⁹.1³,⁷.0¹,²².0⁸,¹³.0¹⁴,²⁸]octacosa-5,16,18,24,26-pentaen-2-one)

3D-SDF for NP0309180 (4-ethenyl-21,24-dihydroxy-10-methyl-15,23-dioxa-25-azaheptacyclo[19.2.2.2¹⁶,¹⁹.1³,⁷.0¹,²².0⁸,¹³.0¹⁴,²⁸]octacosa-5,16,18,24,26-pentaen-2-one)

PDB for NP0309180 (4-ethenyl-21,24-dihydroxy-10-methyl-15,23-dioxa-25-azaheptacyclo[19.2.2.2¹⁶,¹⁹.1³,⁷.0¹,²².0⁸,¹³.0¹⁴,²⁸]octacosa-5,16,18,24,26-pentaen-2-one)

3D PDB for NP0309180 (4-ethenyl-21,24-dihydroxy-10-methyl-15,23-dioxa-25-azaheptacyclo[19.2.2.2¹⁶,¹⁹.1³,⁷.0¹,²².0⁸,¹³.0¹⁴,²⁸]octacosa-5,16,18,24,26-pentaen-2-one)

SMILES for NP0309180 (4-ethenyl-21,24-dihydroxy-10-methyl-15,23-dioxa-25-azaheptacyclo[19.2.2.2¹⁶,¹⁹.1³,⁷.0¹,²².0⁸,¹³.0¹⁴,²⁸]octacosa-5,16,18,24,26-pentaen-2-one)

INCHI for NP0309180 (4-ethenyl-21,24-dihydroxy-10-methyl-15,23-dioxa-25-azaheptacyclo[19.2.2.2¹⁶,¹⁹.1³,⁷.0¹,²².0⁸,¹³.0¹⁴,²⁸]octacosa-5,16,18,24,26-pentaen-2-one)

Structure for NP0309180 (4-ethenyl-21,24-dihydroxy-10-methyl-15,23-dioxa-25-azaheptacyclo[19.2.2.2¹⁶,¹⁹.1³,⁷.0¹,²².0⁸,¹³.0¹⁴,²⁸]octacosa-5,16,18,24,26-pentaen-2-one)

3D Structure for NP0309180 (4-ethenyl-21,24-dihydroxy-10-methyl-15,23-dioxa-25-azaheptacyclo[19.2.2.2¹⁶,¹⁹.1³,⁷.0¹,²².0⁸,¹³.0¹⁴,²⁸]octacosa-5,16,18,24,26-pentaen-2-one)