NP-MRD: Showing NP-Card for 17,19-dihydroxy-7-methyl-13-(prop-1-en-1-yl)-2-oxa-18-azahexacyclo[19.2.2.1³,¹⁰.1¹⁶,¹⁹.0⁴,⁹.0¹⁴,²⁷]heptacosa-1(23),11,17,21,24-pentaen-15-one (NP0155821)

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Record Information

Version

2.0

Created at

2022-09-02 12:57:00 UTC

Updated at

2022-09-02 12:57:00 UTC

NP-MRD ID

NP0155821

Secondary Accession Numbers

None

Natural Product Identification

Common Name

17,19-dihydroxy-7-methyl-13-(prop-1-en-1-yl)-2-oxa-18-azahexacyclo[19.2.2.1³,¹⁰.1¹⁶,¹⁹.0⁴,⁹.0¹⁴,²⁷]heptacosa-1(23),11,17,21,24-pentaen-15-one

Description

17,19-Dihydroxy-7-methyl-13-(prop-1-en-1-yl)-2-oxa-18-azahexacyclo[19.2.2.1³,¹⁰.1¹⁶,¹⁹.0⁴,⁹.0¹⁴,²⁷]Heptacosa-1(23),11,17,21,24-pentaen-15-one 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. 17,19-dihydroxy-7-methyl-13-(prop-1-en-1-yl)-2-oxa-18-azahexacyclo[19.2.2.1³,¹⁰.1¹⁶,¹⁹.0⁴,⁹.0¹⁴,²⁷]heptacosa-1(23),11,17,21,24-pentaen-15-one is found in Hirsutella nivea. 17,19-Dihydroxy-7-methyl-13-(prop-1-en-1-yl)-2-oxa-18-azahexacyclo[19.2.2.1³,¹⁰.1¹⁶,¹⁹.0⁴,⁹.0¹⁴,²⁷]Heptacosa-1(23),11,17,21,24-pentaen-15-one is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004241509212D          

 34 39  0  0  0  0            999 V2000
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M  END

     RDKit          3D

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M  END


  Mrv1533004241509212D          

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 19 20  2  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 22 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  2  0  0  0  0
 26 28  1  0  0  0  0
 22 28  1  0  0  0  0
 25 29  1  0  0  0  0
 29 30  2  0  0  0  0
 29 31  1  0  0  0  0
  4 31  1  0  0  0  0
 31 32  1  0  0  0  0
  7 32  1  0  0  0  0
 15 32  1  0  0  0  0
 20 33  1  0  0  0  0
 33 34  2  0  0  0  0
 17 34  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0155821

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC=CC1C=CC2C3CC(C)CCC3C3OC4=CC=C(CC5(O)CC(C(=O)N5)C(=O)C1C23)C=C4

> <INCHI_IDENTIFIER>
InChI=1S/C29H35NO4/c1-3-4-18-8-12-20-22-13-16(2)5-11-21(22)27-25(20)24(18)26(31)23-15-29(33,30-28(23)32)14-17-6-9-19(34-27)10-7-17/h3-4,6-10,12,16,18,20-25,27,33H,5,11,13-15H2,1-2H3,(H,30,32)

> <INCHI_KEY>
BDMMASMTKZZIAT-UHFFFAOYSA-N

> <FORMULA>
C29H35NO4

> <MOLECULAR_WEIGHT>
461.602

> <EXACT_MASS>
461.256608611

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
69

> <JCHEM_AVERAGE_POLARIZABILITY>
51.531784139519125

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
19-hydroxy-7-methyl-13-(prop-1-en-1-yl)-2-oxa-18-azahexacyclo[19.2.2.1³,¹⁰.1¹⁶,¹⁹.0⁴,⁹.0¹⁴,²⁷]heptacosa-1(23),11,21,24-tetraene-15,17-dione

> <ALOGPS_LOGP>
3.65

> <JCHEM_LOGP>
4.447769258333334

> <ALOGPS_LOGS>
-5.38

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.66182425248098

> <JCHEM_PKA_STRONGEST_ACIDIC>
10.69862200269775

> <JCHEM_PKA_STRONGEST_BASIC>
-3.5768300423643336

> <JCHEM_POLAR_SURFACE_AREA>
75.63

> <JCHEM_REFRACTIVITY>
132.67159999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.92e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
19-hydroxy-7-methyl-13-(prop-1-en-1-yl)-2-oxa-18-azahexacyclo[19.2.2.1³,¹⁰.1¹⁶,¹⁹.0⁴,⁹.0¹⁴,²⁷]heptacosa-1(23),11,21,24-tetraene-15,17-dione

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 24-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-APR-15         0                                  
HETATM    1  C   UNK     0       3.615  -9.642   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       4.900  -8.793   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       4.807  -7.255   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       3.429  -6.568   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.157  -7.452   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.757  -6.787   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.605  -5.225   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -0.686  -4.313   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -2.183  -4.672   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -3.242  -3.554   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -4.740  -3.912   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -2.804  -2.078   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -1.306  -1.719   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -0.247  -2.837   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       1.310  -2.809   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       1.194  -1.185   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       2.057   0.172   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       3.025  -1.040   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       4.548  -0.902   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       5.274   0.450   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       6.686  -0.371   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       7.505  -1.796   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       8.744  -0.881   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0       6.216  -2.646   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       6.402  -4.194   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       7.946  -4.385   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0       8.701  -5.727   0.000  0.00  0.00           O+0
HETATM   28  N   UNK     0       8.587  -2.957   0.000  0.00  0.00           N+0
HETATM   29  C   UNK     0       4.980  -4.915   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0       5.383  -6.401   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0       3.370  -5.012   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       1.881  -4.314   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       4.302   1.696   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       2.763   1.577   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5   31                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8   32                                                  
CONECT    8    7    9   14                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13    8   15                                                  
CONECT   15   14   16   32                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18   34                                                  
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21   33                                                  
CONECT   21   20   22                                                       
CONECT   22   21   23   24   28                                             
CONECT   23   22                                                            
CONECT   24   22   25                                                       
CONECT   25   24   26   29                                                  
CONECT   26   25   27   28                                                  
CONECT   27   26                                                            
CONECT   28   26   22                                                       
CONECT   29   25   30   31                                                  
CONECT   30   29                                                            
CONECT   31   29    4   32                                                  
CONECT   32   31    7   15                                                  
CONECT   33   20   34                                                       
CONECT   34   33   17                                                       
MASTER        0    0    0    0    0    0    0    0   34    0   78    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₉H₃₅NO₄

Average Mass

461.6020 Da

Monoisotopic Mass

461.25661 Da

IUPAC Name

19-hydroxy-7-methyl-13-(prop-1-en-1-yl)-2-oxa-18-azahexacyclo[19.2.2.1³,¹⁰.1¹⁶,¹⁹.0⁴,⁹.0¹⁴,²⁷]heptacosa-1(23),11,21,24-tetraene-15,17-dione

Traditional Name

19-hydroxy-7-methyl-13-(prop-1-en-1-yl)-2-oxa-18-azahexacyclo[19.2.2.1³,¹⁰.1¹⁶,¹⁹.0⁴,⁹.0¹⁴,²⁷]heptacosa-1(23),11,21,24-tetraene-15,17-dione

CAS Registry Number

Not Available

SMILES

CC=CC1C=CC2C3CC(C)CCC3C3OC4=CC=C(CC5(O)CC(C(=O)N5)C(=O)C1C23)C=C4

InChI Identifier

InChI=1S/C29H35NO4/c1-3-4-18-8-12-20-22-13-16(2)5-11-21(22)27-25(20)24(18)26(31)23-15-29(33,30-28(23)32)14-17-6-9-19(34-27)10-7-17/h3-4,6-10,12,16,18,20-25,27,33H,5,11,13-15H2,1-2H3,(H,30,32)

InChI Key

BDMMASMTKZZIAT-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
Pyrrolidone
Benzenoid
1,3-dicarbonyl compound
2-pyrrolidone
Pyrrolidine
Carboxamide group
Ketone
Lactam
Secondary carboxylic acid amide
Alkanolamine
Carboxylic acid derivative
Ether
Oxacycle
Azacycle
Organoheterocyclic compound
Organic oxide
Organopnictogen compound
Hydrocarbon derivative
Organonitrogen compound
Organooxygen compound
Carbonyl group
Organic oxygen compound
Organic nitrogen compound
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	3.65	ALOGPS
logP	4.45	ChemAxon
logS	-5.4	ALOGPS
pKa (Strongest Acidic)	10.7	ChemAxon
pKa (Strongest Basic)	-3.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	75.63 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	132.67 m³·mol⁻¹	ChemAxon
Polarizability	51.53 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

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

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 17,19-dihydroxy-7-methyl-13-(prop-1-en-1-yl)-2-oxa-18-azahexacyclo[19.2.2.1³,¹⁰.1¹⁶,¹⁹.0⁴,⁹.0¹⁴,²⁷]heptacosa-1(23),11,17,21,24-pentaen-15-one (NP0155821)

MOL for NP0155821 (17,19-dihydroxy-7-methyl-13-(prop-1-en-1-yl)-2-oxa-18-azahexacyclo[19.2.2.1³,¹⁰.1¹⁶,¹⁹.0⁴,⁹.0¹⁴,²⁷]heptacosa-1(23),11,17,21,24-pentaen-15-one)

3D MOL for NP0155821 (17,19-dihydroxy-7-methyl-13-(prop-1-en-1-yl)-2-oxa-18-azahexacyclo[19.2.2.1³,¹⁰.1¹⁶,¹⁹.0⁴,⁹.0¹⁴,²⁷]heptacosa-1(23),11,17,21,24-pentaen-15-one)

3D SDF for NP0155821 (17,19-dihydroxy-7-methyl-13-(prop-1-en-1-yl)-2-oxa-18-azahexacyclo[19.2.2.1³,¹⁰.1¹⁶,¹⁹.0⁴,⁹.0¹⁴,²⁷]heptacosa-1(23),11,17,21,24-pentaen-15-one)

3D-SDF for NP0155821 (17,19-dihydroxy-7-methyl-13-(prop-1-en-1-yl)-2-oxa-18-azahexacyclo[19.2.2.1³,¹⁰.1¹⁶,¹⁹.0⁴,⁹.0¹⁴,²⁷]heptacosa-1(23),11,17,21,24-pentaen-15-one)

PDB for NP0155821 (17,19-dihydroxy-7-methyl-13-(prop-1-en-1-yl)-2-oxa-18-azahexacyclo[19.2.2.1³,¹⁰.1¹⁶,¹⁹.0⁴,⁹.0¹⁴,²⁷]heptacosa-1(23),11,17,21,24-pentaen-15-one)

3D PDB for NP0155821 (17,19-dihydroxy-7-methyl-13-(prop-1-en-1-yl)-2-oxa-18-azahexacyclo[19.2.2.1³,¹⁰.1¹⁶,¹⁹.0⁴,⁹.0¹⁴,²⁷]heptacosa-1(23),11,17,21,24-pentaen-15-one)

SMILES for NP0155821 (17,19-dihydroxy-7-methyl-13-(prop-1-en-1-yl)-2-oxa-18-azahexacyclo[19.2.2.1³,¹⁰.1¹⁶,¹⁹.0⁴,⁹.0¹⁴,²⁷]heptacosa-1(23),11,17,21,24-pentaen-15-one)

INCHI for NP0155821 (17,19-dihydroxy-7-methyl-13-(prop-1-en-1-yl)-2-oxa-18-azahexacyclo[19.2.2.1³,¹⁰.1¹⁶,¹⁹.0⁴,⁹.0¹⁴,²⁷]heptacosa-1(23),11,17,21,24-pentaen-15-one)

Structure for NP0155821 (17,19-dihydroxy-7-methyl-13-(prop-1-en-1-yl)-2-oxa-18-azahexacyclo[19.2.2.1³,¹⁰.1¹⁶,¹⁹.0⁴,⁹.0¹⁴,²⁷]heptacosa-1(23),11,17,21,24-pentaen-15-one)

3D Structure for NP0155821 (17,19-dihydroxy-7-methyl-13-(prop-1-en-1-yl)-2-oxa-18-azahexacyclo[19.2.2.1³,¹⁰.1¹⁶,¹⁹.0⁴,⁹.0¹⁴,²⁷]heptacosa-1(23),11,17,21,24-pentaen-15-one)