NP-MRD: Showing NP-Card for (1r,4s,7s,9s)-6,9-dihydroxy-7-methyl-4-{[7-(3-methylbut-2-en-1-yl)-1h-indol-3-yl]methyl}-2,5,16-triazatetracyclo[7.7.0.0²,⁷.0¹⁰,¹⁵]hexadeca-5,10,12,14-tetraen-3-one (NP0165246)

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Record Information

Version

2.0

Created at

2022-09-03 00:19:06 UTC

Updated at

2022-09-03 00:19:06 UTC

NP-MRD ID

NP0165246

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1r,4s,7s,9s)-6,9-dihydroxy-7-methyl-4-{[7-(3-methylbut-2-en-1-yl)-1h-indol-3-yl]methyl}-2,5,16-triazatetracyclo[7.7.0.0²,⁷.0¹⁰,¹⁵]hexadeca-5,10,12,14-tetraen-3-one

Description

(1R,4S,7S,9S)-6,9-dihydroxy-7-methyl-4-{[7-(3-methylbut-2-en-1-yl)-1H-indol-3-yl]methyl}-2,5,16-triazatetracyclo[7.7.0.0²,⁷.0¹⁰,¹⁵]Hexadeca-5,10,12,14-tetraen-3-one belongs to the class of organic compounds known as pyrroloindoles. Pyrroloindoles are compounds containing a pyrroloindole moiety, which is a tricyclic heterocycle which consists of a pyrrole ring fused to an indole. Pyrrole is 5-membered ring consisting of four carbon atoms and one nitrogen atom. Indole is a bicyclic compound consisting of a six-membered benzene ring fused to a five-membered nitrogen-containing pyrrole ring. (1r,4s,7s,9s)-6,9-dihydroxy-7-methyl-4-{[7-(3-methylbut-2-en-1-yl)-1h-indol-3-yl]methyl}-2,5,16-triazatetracyclo[7.7.0.0²,⁷.0¹⁰,¹⁵]hexadeca-5,10,12,14-tetraen-3-one is found in Aspergillus taichungensis. Based on a literature review very few articles have been published on (1R,4S,7S,9S)-6,9-dihydroxy-7-methyl-4-{[7-(3-methylbut-2-en-1-yl)-1H-indol-3-yl]methyl}-2,5,16-triazatetracyclo[7.7.0.0²,⁷.0¹⁰,¹⁵]Hexadeca-5,10,12,14-tetraen-3-one.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309032202192D          

 35 40  0  0  1  0            999 V2000
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M  END

     RDKit          3D

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M  END


  Mrv1652309032202192D          

 35 40  0  0  1  0            999 V2000
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 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  2  0  0  0  0
 22 27  1  0  0  0  0
 27 28  1  0  0  0  0
 29 28  1  6  0  0  0
 20 29  1  0  0  0  0
 29 30  1  0  0  0  0
 17 30  1  0  0  0  0
 30 31  1  0  0  0  0
 13 31  1  0  0  0  0
 31 32  2  0  0  0  0
 11 33  2  0  0  0  0
 33 34  1  0  0  0  0
 34 35  1  0  0  0  0
  6 35  2  0  0  0  0
 10 35  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0165246

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)=CCC1=C2NC=C(C[C@@H]3N=C(O)[C@]4(C)C[C@@]5(O)[C@H](NC6=CC=CC=C56)N4C3=O)C2=CC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C28H30N4O3/c1-16(2)11-12-17-7-6-8-19-18(14-29-23(17)19)13-22-24(33)32-25-28(35,15-27(32,3)26(34)31-22)20-9-4-5-10-21(20)30-25/h4-11,14,22,25,29-30,35H,12-13,15H2,1-3H3,(H,31,34)/t22-,25+,27-,28-/m0/s1

> <INCHI_KEY>
MAWXLVYQWGQMKX-MZRLSVQCSA-N

> <FORMULA>
C28H30N4O3

> <MOLECULAR_WEIGHT>
470.573

> <EXACT_MASS>
470.231790842

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
65

> <JCHEM_AVERAGE_POLARIZABILITY>
51.70620785179555

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1R,4S,7S,9S)-6,9-dihydroxy-7-methyl-4-{[7-(3-methylbut-2-en-1-yl)-1H-indol-3-yl]methyl}-2,5,16-triazatetracyclo[7.7.0.0^{2,7}.0^{10,15}]hexadeca-5,10,12,14-tetraen-3-one

> <ALOGPS_LOGP>
3.63

> <JCHEM_LOGP>
4.0633284283333335

> <ALOGPS_LOGS>
-4.30

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.047090318463667

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.3787705601629785

> <JCHEM_PKA_STRONGEST_BASIC>
1.3195255761795197

> <JCHEM_POLAR_SURFACE_AREA>
100.95

> <JCHEM_REFRACTIVITY>
136.24970000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.37e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1R,4S,7S,9S)-6,9-dihydroxy-7-methyl-4-{[7-(3-methylbut-2-en-1-yl)-1H-indol-3-yl]methyl}-2,5,16-triazatetracyclo[7.7.0.0^{2,7}.0^{10,15}]hexadeca-5,10,12,14-tetraen-3-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 03-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   03-SEP-22         0                                  
HETATM    1  C   UNK     0      12.567  -6.024   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      11.234  -6.794   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      11.234  -8.334   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       9.900  -6.024   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       8.566  -6.794   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       8.566  -8.334   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       9.900  -9.104   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       9.900 -10.644   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       8.566 -11.414   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       7.233 -10.644   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.768 -11.120   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       5.292 -12.584   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       6.323 -13.729   0.000  0.00  0.00           C+0
HETATM   14  N   UNK     0       7.829 -13.408   0.000  0.00  0.00           N+0
HETATM   15  C   UNK     0       8.860 -14.553   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      10.366 -14.233   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       8.384 -16.018   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       9.915 -15.857   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       9.154 -17.351   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       8.123 -18.496   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       9.530 -19.122   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       7.962 -20.027   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       8.993 -21.172   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       8.517 -22.636   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       7.010 -22.956   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       5.980 -21.812   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       6.456 -20.347   0.000  0.00  0.00           C+0
HETATM   28  N   UNK     0       5.686 -19.014   0.000  0.00  0.00           N+0
HETATM   29  C   UNK     0       6.716 -17.869   0.000  0.00  0.00           C+0
HETATM   30  N   UNK     0       6.877 -16.338   0.000  0.00  0.00           N+0
HETATM   31  C   UNK     0       5.847 -15.193   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0       4.340 -15.513   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0       4.863  -9.874   0.000  0.00  0.00           C+0
HETATM   34  N   UNK     0       5.768  -8.628   0.000  0.00  0.00           N+0
HETATM   35  C   UNK     0       7.233  -9.104   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7   35                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11   35                                                  
CONECT   11   10   12   33                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14   31                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15   18   19   30                                             
CONECT   18   17                                                            
CONECT   19   17   20                                                       
CONECT   20   19   21   22   29                                             
CONECT   21   20                                                            
CONECT   22   20   23   27                                                  
CONECT   23   22   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24   26                                                       
CONECT   26   25   27                                                       
CONECT   27   26   22   28                                                  
CONECT   28   27   29                                                       
CONECT   29   28   20   30                                                  
CONECT   30   29   17   31                                                  
CONECT   31   30   13   32                                                  
CONECT   32   31                                                            
CONECT   33   11   34                                                       
CONECT   34   33   35                                                       
CONECT   35   34    6   10                                                  
MASTER        0    0    0    0    0    0    0    0   35    0   80    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₈H₃₀N₄O₃

Average Mass

470.5730 Da

Monoisotopic Mass

470.23179 Da

IUPAC Name

(1R,4S,7S,9S)-6,9-dihydroxy-7-methyl-4-{[7-(3-methylbut-2-en-1-yl)-1H-indol-3-yl]methyl}-2,5,16-triazatetracyclo[7.7.0.0^{2,7}.0^{10,15}]hexadeca-5,10,12,14-tetraen-3-one

Traditional Name

(1R,4S,7S,9S)-6,9-dihydroxy-7-methyl-4-{[7-(3-methylbut-2-en-1-yl)-1H-indol-3-yl]methyl}-2,5,16-triazatetracyclo[7.7.0.0^{2,7}.0^{10,15}]hexadeca-5,10,12,14-tetraen-3-one

CAS Registry Number

Not Available

SMILES

CC(C)=CCC1=C2NC=C(C[C@@H]3N=C(O)[C@]4(C)C[C@@]5(O)[C@H](NC6=CC=CC=C56)N4C3=O)C2=CC=C1

InChI Identifier

InChI=1S/C28H30N4O3/c1-16(2)11-12-17-7-6-8-19-18(14-29-23(17)19)13-22-24(33)32-25-28(35,15-27(32,3)26(34)31-22)20-9-4-5-10-21(20)30-25/h4-11,14,22,25,29-30,35H,12-13,15H2,1-3H3,(H,31,34)/t22-,25+,27-,28-/m0/s1

InChI Key

MAWXLVYQWGQMKX-MZRLSVQCSA-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
Aspergillus taichungensis	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as pyrroloindoles. Pyrroloindoles are compounds containing a pyrroloindole moiety, which is a tricyclic heterocycle which consists of a pyrrole ring fused to an indole. Pyrrole is 5-membered ring consisting of four carbon atoms and one nitrogen atom. Indole is a bicyclic compound consisting of a six-membered benzene ring fused to a five-membered nitrogen-containing pyrrole ring.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Indoles and derivatives

Sub Class

Pyrroloindoles

Direct Parent

Pyrroloindoles

Alternative Parents

Substituents

Pyrroloindole
3-alkylindole
Alpha-amino acid or derivatives
Dihydroindole
Indole
Secondary aliphatic/aromatic amine
Benzenoid
Substituted pyrrole
Heteroaromatic compound
Cyclic carboximidic acid
Tertiary carboxylic acid amide
Tertiary alcohol
Pyrrolidine
Pyrrole
Lactam
Carboxamide group
Amino acid or derivatives
Azacycle
Organic 1,3-dipolar compound
Propargyl-type 1,3-dipolar organic compound
Secondary amine
Carboxylic acid derivative
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
Carbonyl group
Amine
Alcohol
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	3.63	ALOGPS
logP	4.06	ChemAxon
logS	-4.3	ALOGPS
pKa (Strongest Acidic)	4.38	ChemAxon
pKa (Strongest Basic)	1.32	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	100.95 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	136.25 m³·mol⁻¹	ChemAxon
Polarizability	51.71 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

78438694

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

139588747

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (1r,4s,7s,9s)-6,9-dihydroxy-7-methyl-4-{[7-(3-methylbut-2-en-1-yl)-1h-indol-3-yl]methyl}-2,5,16-triazatetracyclo[7.7.0.0²,⁷.0¹⁰,¹⁵]hexadeca-5,10,12,14-tetraen-3-one (NP0165246)

MOL for NP0165246 ((1r,4s,7s,9s)-6,9-dihydroxy-7-methyl-4-{[7-(3-methylbut-2-en-1-yl)-1h-indol-3-yl]methyl}-2,5,16-triazatetracyclo[7.7.0.0²,⁷.0¹⁰,¹⁵]hexadeca-5,10,12,14-tetraen-3-one)

3D MOL for NP0165246 ((1r,4s,7s,9s)-6,9-dihydroxy-7-methyl-4-{[7-(3-methylbut-2-en-1-yl)-1h-indol-3-yl]methyl}-2,5,16-triazatetracyclo[7.7.0.0²,⁷.0¹⁰,¹⁵]hexadeca-5,10,12,14-tetraen-3-one)

3D SDF for NP0165246 ((1r,4s,7s,9s)-6,9-dihydroxy-7-methyl-4-{[7-(3-methylbut-2-en-1-yl)-1h-indol-3-yl]methyl}-2,5,16-triazatetracyclo[7.7.0.0²,⁷.0¹⁰,¹⁵]hexadeca-5,10,12,14-tetraen-3-one)

3D-SDF for NP0165246 ((1r,4s,7s,9s)-6,9-dihydroxy-7-methyl-4-{[7-(3-methylbut-2-en-1-yl)-1h-indol-3-yl]methyl}-2,5,16-triazatetracyclo[7.7.0.0²,⁷.0¹⁰,¹⁵]hexadeca-5,10,12,14-tetraen-3-one)

PDB for NP0165246 ((1r,4s,7s,9s)-6,9-dihydroxy-7-methyl-4-{[7-(3-methylbut-2-en-1-yl)-1h-indol-3-yl]methyl}-2,5,16-triazatetracyclo[7.7.0.0²,⁷.0¹⁰,¹⁵]hexadeca-5,10,12,14-tetraen-3-one)

3D PDB for NP0165246 ((1r,4s,7s,9s)-6,9-dihydroxy-7-methyl-4-{[7-(3-methylbut-2-en-1-yl)-1h-indol-3-yl]methyl}-2,5,16-triazatetracyclo[7.7.0.0²,⁷.0¹⁰,¹⁵]hexadeca-5,10,12,14-tetraen-3-one)

SMILES for NP0165246 ((1r,4s,7s,9s)-6,9-dihydroxy-7-methyl-4-{[7-(3-methylbut-2-en-1-yl)-1h-indol-3-yl]methyl}-2,5,16-triazatetracyclo[7.7.0.0²,⁷.0¹⁰,¹⁵]hexadeca-5,10,12,14-tetraen-3-one)

INCHI for NP0165246 ((1r,4s,7s,9s)-6,9-dihydroxy-7-methyl-4-{[7-(3-methylbut-2-en-1-yl)-1h-indol-3-yl]methyl}-2,5,16-triazatetracyclo[7.7.0.0²,⁷.0¹⁰,¹⁵]hexadeca-5,10,12,14-tetraen-3-one)

Structure for NP0165246 ((1r,4s,7s,9s)-6,9-dihydroxy-7-methyl-4-{[7-(3-methylbut-2-en-1-yl)-1h-indol-3-yl]methyl}-2,5,16-triazatetracyclo[7.7.0.0²,⁷.0¹⁰,¹⁵]hexadeca-5,10,12,14-tetraen-3-one)

3D Structure for NP0165246 ((1r,4s,7s,9s)-6,9-dihydroxy-7-methyl-4-{[7-(3-methylbut-2-en-1-yl)-1h-indol-3-yl]methyl}-2,5,16-triazatetracyclo[7.7.0.0²,⁷.0¹⁰,¹⁵]hexadeca-5,10,12,14-tetraen-3-one)