NP-MRD: Showing NP-Card for (3s,6s,9s,17as)-1,4,7,10-tetrahydroxy-3-[(4-hydroxyphenyl)methyl]-9-methyl-6-(2-methylpropyl)-3h,6h,9h,12h,15h,16h,17h,17ah-pyrrolo[1,2-a]1,4,7,10,13-pentaazacyclopentadecan-13-one (NP0305944)

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Record Information

Version

2.0

Created at

2022-09-10 22:07:38 UTC

Updated at

2022-09-10 22:07:38 UTC

NP-MRD ID

NP0305944

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(3s,6s,9s,17as)-1,4,7,10-tetrahydroxy-3-[(4-hydroxyphenyl)methyl]-9-methyl-6-(2-methylpropyl)-3h,6h,9h,12h,15h,16h,17h,17ah-pyrrolo[1,2-a]1,4,7,10,13-pentaazacyclopentadecan-13-one

Description

Pseudostellarin A belongs to the class of organic compounds known as oligopeptides. These are organic compounds containing a sequence of between three and ten alpha-amino acids joined by peptide bonds. (3s,6s,9s,17as)-1,4,7,10-tetrahydroxy-3-[(4-hydroxyphenyl)methyl]-9-methyl-6-(2-methylpropyl)-3h,6h,9h,12h,15h,16h,17h,17ah-pyrrolo[1,2-a]1,4,7,10,13-pentaazacyclopentadecan-13-one is found in Pseudostellaria heterophylla, Stellaria palustris and Stellaria yunnanensis. (3s,6s,9s,17as)-1,4,7,10-tetrahydroxy-3-[(4-hydroxyphenyl)methyl]-9-methyl-6-(2-methylpropyl)-3h,6h,9h,12h,15h,16h,17h,17ah-pyrrolo[1,2-a]1,4,7,10,13-pentaazacyclopentadecan-13-one was first documented in 2015 (PMID: 26137876). Based on a literature review a small amount of articles have been published on Pseudostellarin A (PMID: 35682928) (PMID: 27326468) (PMID: 25869116).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309112200072D          

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M  END

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  7  9  1  0  0  0  0
  9 10  1  1  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 14 16  1  0  0  0  0
 16 17  2  0  0  0  0
 11 17  1  0  0  0  0
  9 18  1  0  0  0  0
 18 19  2  0  0  0  0
 19 20  1  4  0  0  0
 19 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 21 25  1  1  0  0  0
 25 26  1  0  0  0  0
 26 27  2  0  0  0  0
 26 28  1  0  0  0  0
 29 28  1  4  0  0  0
 29 30  2  0  0  0  0
 30 31  1  0  0  0  0
 30 32  1  0  0  0  0
 32 33  1  1  0  0  0
 32 34  1  0  0  0  0
 34 35  2  0  0  0  0
  5 35  1  0  0  0  0
 35 36  1  4  0  0  0
M  END
> <DATABASE_ID>
NP0305944

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)C[C@@H]1N=C(O)[C@H](CC2=CC=C(O)C=C2)N=C(O)[C@@H]2CCCN2C(=O)CN=C(O)[C@H](C)N=C1O

> <INCHI_IDENTIFIER>
InChI=1S/C25H35N5O6/c1-14(2)11-18-23(34)27-15(3)22(33)26-13-21(32)30-10-4-5-20(30)25(36)29-19(24(35)28-18)12-16-6-8-17(31)9-7-16/h6-9,14-15,18-20,31H,4-5,10-13H2,1-3H3,(H,26,33)(H,27,34)(H,28,35)(H,29,36)/t15-,18-,19-,20-/m0/s1

> <INCHI_KEY>
DBUMGRDLKHIWEI-KNTRFNDTSA-N

> <FORMULA>
C25H35N5O6

> <MOLECULAR_WEIGHT>
501.584

> <EXACT_MASS>
501.258733867

> <JCHEM_ACCEPTOR_COUNT>
10

> <JCHEM_ATOM_COUNT>
71

> <JCHEM_AVERAGE_POLARIZABILITY>
52.11924116663622

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(3S,6S,9S,17aS)-1,4,7,10-tetrahydroxy-3-[(4-hydroxyphenyl)methyl]-9-methyl-6-(2-methylpropyl)-3H,6H,9H,12H,13H,15H,16H,17H,17aH-pyrrolo[1,2-a]1,4,7,10,13-pentaazacyclopentadecan-13-one

> <JCHEM_LOGP>
-1.0372108076265552

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
2.566651060666324

> <JCHEM_PKA_STRONGEST_ACIDIC>
-7.66413081583702

> <JCHEM_PKA_STRONGEST_BASIC>
14.729731914214135

> <JCHEM_POLAR_SURFACE_AREA>
170.9

> <JCHEM_REFRACTIVITY>
132.0425

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(3S,6S,9S,17aS)-1,4,7,10-tetrahydroxy-3-[(4-hydroxyphenyl)methyl]-9-methyl-6-(2-methylpropyl)-3H,6H,9H,12H,15H,16H,17H,17aH-pyrrolo[1,2-a]1,4,7,10,13-pentaazacyclopentadecan-13-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      14.470  -3.366   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      14.363  -1.830   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      15.640  -0.969   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      12.979  -1.155   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      11.702  -2.016   0.000  0.00  0.00           C+0
HETATM    6  N   UNK     0      10.318  -1.341   0.000  0.00  0.00           N+0
HETATM    7  C   UNK     0       9.894   0.140   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0      10.964   1.247   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       8.399   0.512   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       7.975   1.993   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       9.045   3.100   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       8.621   4.581   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       9.691   5.689   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      11.185   5.316   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      12.255   6.423   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0      11.609   3.835   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      10.539   2.728   0.000  0.00  0.00           C+0
HETATM   18  N   UNK     0       7.330  -0.595   0.000  0.00  0.00           N+0
HETATM   19  C   UNK     0       5.790  -0.541   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       5.068   0.818   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       4.974  -1.847   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       3.458  -2.114   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       3.243  -3.639   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       4.627  -4.315   0.000  0.00  0.00           C+0
HETATM   25  N   UNK     0       5.697  -3.207   0.000  0.00  0.00           N+0
HETATM   26  C   UNK     0       5.170  -4.654   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0       3.654  -4.921   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0       6.160  -5.834   0.000  0.00  0.00           C+0
HETATM   29  N   UNK     0       7.677  -5.567   0.000  0.00  0.00           N+0
HETATM   30  C   UNK     0       8.890  -6.515   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0       8.676  -8.040   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0      10.318  -5.938   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      11.531  -6.886   0.000  0.00  0.00           C+0
HETATM   34  N   UNK     0      10.532  -4.413   0.000  0.00  0.00           N+0
HETATM   35  C   UNK     0      11.809  -3.552   0.000  0.00  0.00           C+0
HETATM   36  O   UNK     0      13.193  -4.227   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6   35                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10   18                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12   17                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14   17                                                       
CONECT   17   16   11                                                       
CONECT   18    9   19                                                       
CONECT   19   18   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19   22   25                                                  
CONECT   22   21   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24   21   26                                                  
CONECT   26   25   27   28                                                  
CONECT   27   26                                                            
CONECT   28   26   29                                                       
CONECT   29   28   30                                                       
CONECT   30   29   31   32                                                  
CONECT   31   30                                                            
CONECT   32   30   33   34                                                  
CONECT   33   32                                                            
CONECT   34   32   35                                                       
CONECT   35   34    5   36                                                  
CONECT   36   35                                                            
MASTER        0    0    0    0    0    0    0    0   36    0   76    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₅H₃₅N₅O₆

Average Mass

501.5840 Da

Monoisotopic Mass

501.25873 Da

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

CC(C)C[C@@H]1N=C(O)[C@H](CC2=CC=C(O)C=C2)N=C(O)[C@@H]2CCCN2C(=O)CN=C(O)[C@H](C)N=C1O

InChI Identifier

InChI=1S/C25H35N5O6/c1-14(2)11-18-23(34)27-15(3)22(33)26-13-21(32)30-10-4-5-20(30)25(36)29-19(24(35)28-18)12-16-6-8-17(31)9-7-16/h6-9,14-15,18-20,31H,4-5,10-13H2,1-3H3,(H,26,33)(H,27,34)(H,28,35)(H,29,36)/t15-,18-,19-,20-/m0/s1

InChI Key

DBUMGRDLKHIWEI-KNTRFNDTSA-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
Pseudostellaria heterophylla	LOTUS Database	35616633
Stellaria palustris	LOTUS Database	35616633
Stellaria yunnanensis	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as oligopeptides. These are organic compounds containing a sequence of between three and ten alpha-amino acids joined by peptide bonds.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

Oligopeptides

Alternative Parents

Substituents

Alpha-oligopeptide
Cyclic alpha peptide
Macrolactam
Alpha-amino acid or derivatives
1-hydroxy-2-unsubstituted benzenoid
Phenol
Monocyclic benzene moiety
Benzenoid
Pyrrolidine
Tertiary carboxylic acid amide
Secondary carboxylic acid amide
Lactam
Carboxamide group
Azacycle
Organoheterocyclic compound
Organic nitrogen compound
Organooxygen compound
Organonitrogen compound
Hydrocarbon derivative
Organic oxide
Carbonyl group
Organic oxygen 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

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00028874

Chemspider ID

8566751

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

10391309

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Honisch C, Gazziero M, Dallocchio R, Dessi A, Fabbri D, Dettori MA, Delogu G, Ruzza P: Antamanide Analogs as Potential Inhibitors of Tyrosinase. Int J Mol Sci. 2022 Jun 2;23(11):6240. doi: 10.3390/ijms23116240. [PubMed:35682928 ]
Zhang S, Amso Z, De Leon Rodriguez LM, Kaur H, Brimble MA: Synthesis of Natural Cyclopentapeptides Isolated from Dianthus chinensis. J Nat Prod. 2016 Jul 22;79(7):1769-74. doi: 10.1021/acs.jnatprod.6b00152. Epub 2016 Jun 21. [PubMed:27326468 ]
Wang J, Li J, Li H, Wu X, Gao W: HPLC-ESI-MS(n) Analysis, Fed-Batch Cultivation Enhances Bioactive Compound Biosynthesis and Immune-Regulative Effect of Adventitious Roots in Pseudostellaria heterophylla. Appl Biochem Biotechnol. 2015 Sep;177(1):63-75. doi: 10.1007/s12010-015-1728-6. Epub 2015 Jul 3. [PubMed:26137876 ]
Han J, Huang M, Wang Z, Zheng Y, Zeng G, He W, Tan N: Cyclopentapeptides from Dianthus chinensis. J Pept Sci. 2015 Jul;21(7):550-3. doi: 10.1002/psc.2746. Epub 2015 Apr 13. [PubMed:25869116 ]
LOTUS database [Link]

Showing NP-Card for (3s,6s,9s,17as)-1,4,7,10-tetrahydroxy-3-[(4-hydroxyphenyl)methyl]-9-methyl-6-(2-methylpropyl)-3h,6h,9h,12h,15h,16h,17h,17ah-pyrrolo[1,2-a]1,4,7,10,13-pentaazacyclopentadecan-13-one (NP0305944)

MOL for NP0305944 ((3s,6s,9s,17as)-1,4,7,10-tetrahydroxy-3-[(4-hydroxyphenyl)methyl]-9-methyl-6-(2-methylpropyl)-3h,6h,9h,12h,15h,16h,17h,17ah-pyrrolo[1,2-a]1,4,7,10,13-pentaazacyclopentadecan-13-one)

3D MOL for NP0305944 ((3s,6s,9s,17as)-1,4,7,10-tetrahydroxy-3-[(4-hydroxyphenyl)methyl]-9-methyl-6-(2-methylpropyl)-3h,6h,9h,12h,15h,16h,17h,17ah-pyrrolo[1,2-a]1,4,7,10,13-pentaazacyclopentadecan-13-one)

3D SDF for NP0305944 ((3s,6s,9s,17as)-1,4,7,10-tetrahydroxy-3-[(4-hydroxyphenyl)methyl]-9-methyl-6-(2-methylpropyl)-3h,6h,9h,12h,15h,16h,17h,17ah-pyrrolo[1,2-a]1,4,7,10,13-pentaazacyclopentadecan-13-one)

3D-SDF for NP0305944 ((3s,6s,9s,17as)-1,4,7,10-tetrahydroxy-3-[(4-hydroxyphenyl)methyl]-9-methyl-6-(2-methylpropyl)-3h,6h,9h,12h,15h,16h,17h,17ah-pyrrolo[1,2-a]1,4,7,10,13-pentaazacyclopentadecan-13-one)

PDB for NP0305944 ((3s,6s,9s,17as)-1,4,7,10-tetrahydroxy-3-[(4-hydroxyphenyl)methyl]-9-methyl-6-(2-methylpropyl)-3h,6h,9h,12h,15h,16h,17h,17ah-pyrrolo[1,2-a]1,4,7,10,13-pentaazacyclopentadecan-13-one)

3D PDB for NP0305944 ((3s,6s,9s,17as)-1,4,7,10-tetrahydroxy-3-[(4-hydroxyphenyl)methyl]-9-methyl-6-(2-methylpropyl)-3h,6h,9h,12h,15h,16h,17h,17ah-pyrrolo[1,2-a]1,4,7,10,13-pentaazacyclopentadecan-13-one)

SMILES for NP0305944 ((3s,6s,9s,17as)-1,4,7,10-tetrahydroxy-3-[(4-hydroxyphenyl)methyl]-9-methyl-6-(2-methylpropyl)-3h,6h,9h,12h,15h,16h,17h,17ah-pyrrolo[1,2-a]1,4,7,10,13-pentaazacyclopentadecan-13-one)

INCHI for NP0305944 ((3s,6s,9s,17as)-1,4,7,10-tetrahydroxy-3-[(4-hydroxyphenyl)methyl]-9-methyl-6-(2-methylpropyl)-3h,6h,9h,12h,15h,16h,17h,17ah-pyrrolo[1,2-a]1,4,7,10,13-pentaazacyclopentadecan-13-one)

Structure for NP0305944 ((3s,6s,9s,17as)-1,4,7,10-tetrahydroxy-3-[(4-hydroxyphenyl)methyl]-9-methyl-6-(2-methylpropyl)-3h,6h,9h,12h,15h,16h,17h,17ah-pyrrolo[1,2-a]1,4,7,10,13-pentaazacyclopentadecan-13-one)

3D Structure for NP0305944 ((3s,6s,9s,17as)-1,4,7,10-tetrahydroxy-3-[(4-hydroxyphenyl)methyl]-9-methyl-6-(2-methylpropyl)-3h,6h,9h,12h,15h,16h,17h,17ah-pyrrolo[1,2-a]1,4,7,10,13-pentaazacyclopentadecan-13-one)