NP-MRD: Showing NP-Card for (1's,2s,3's,7's)-13'-hydroxy-4',4',6,6-tetramethyl-1h-9',14'-diazaspiro[chromeno[6,7-b]pyrrole-2,5'-tetracyclo[5.5.2.0¹,⁹.0³,⁷]tetradecan]-13'-ene-3,8'-dione (NP0314543)

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Record Information

Version

2.0

Created at

2022-09-11 12:41:31 UTC

Updated at

2022-09-11 12:41:31 UTC

NP-MRD ID

NP0314543

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1's,2s,3's,7's)-13'-hydroxy-4',4',6,6-tetramethyl-1h-9',14'-diazaspiro[chromeno[6,7-b]pyrrole-2,5'-tetracyclo[5.5.2.0¹,⁹.0³,⁷]tetradecan]-13'-ene-3,8'-dione

Description

(1'S,2S,3'S,7'S)-13'-hydroxy-4',4',6,6-tetramethyl-3,6-dihydro-1H-9',14'-diazaspiro[chromeno[6,7-b]pyrrole-2,5'-tetracyclo[5.5.2.0¹,⁹.0³,⁷]Tetradecan]-13'-ene-3,8'-dione belongs to the class of organic compounds known as 2,2-dimethyl-1-benzopyrans. These are organic compounds containing a 1-benzopyran moiety that carries two methyl groups at the 2-position. (1's,2s,3's,7's)-13'-hydroxy-4',4',6,6-tetramethyl-1h-9',14'-diazaspiro[chromeno[6,7-b]pyrrole-2,5'-tetracyclo[5.5.2.0¹,⁹.0³,⁷]tetradecan]-13'-ene-3,8'-dione is found in Aspergillus ochraceus. Based on a literature review very few articles have been published on (1'S,2S,3'S,7'S)-13'-hydroxy-4',4',6,6-tetramethyl-3,6-dihydro-1H-9',14'-diazaspiro[chromeno[6,7-b]pyrrole-2,5'-tetracyclo[5.5.2.0¹,⁹.0³,⁷]Tetradecan]-13'-ene-3,8'-dione.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309112214412D          

 33 39  0  0  1  0            999 V2000
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M  END

     RDKit          3D

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M  END


  Mrv1652309112214412D          

 33 39  0  0  1  0            999 V2000
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M  END
> <DATABASE_ID>
NP0314543

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1(C)[C@@H]2C[C@]34CCCN3C(=O)[C@@]2(C[C@]11NC2=C(C=C3OC(C)(C)C=CC3=C2)C1=O)N=C4O

> <INCHI_IDENTIFIER>
InChI=1S/C26H29N3O4/c1-22(2)8-6-14-10-16-15(11-17(14)33-22)19(30)26(27-16)13-25-18(23(26,3)4)12-24(20(31)28-25)7-5-9-29(24)21(25)32/h6,8,10-11,18,27H,5,7,9,12-13H2,1-4H3,(H,28,31)/t18-,24-,25-,26+/m0/s1

> <INCHI_KEY>
VPZPMWLDKGSQNB-YCYYUTJKSA-N

> <FORMULA>
C26H29N3O4

> <MOLECULAR_WEIGHT>
447.535

> <EXACT_MASS>
447.215806426

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
62

> <JCHEM_AVERAGE_POLARIZABILITY>
48.934207067277455

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1'S,2S,3'S,7'S)-13'-hydroxy-4',4',6,6-tetramethyl-3,6-dihydro-1H-9',14'-diazaspiro[chromeno[6,7-b]pyrrole-2,5'-tetracyclo[5.5.2.0^{1,9}.0^{3,7}]tetradecan]-13'-ene-3,8'-dione

> <JCHEM_LOGP>
3.2865236056666665

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
7

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
11.75227794265611

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.9856769953381215

> <JCHEM_PKA_STRONGEST_BASIC>
0.984675253108148

> <JCHEM_POLAR_SURFACE_AREA>
91.23

> <JCHEM_REFRACTIVITY>
124.23239999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(1'S,2S,3'S,7'S)-13'-hydroxy-4',4',6,6-tetramethyl-1H-9',14'-diazaspiro[chromeno[6,7-b]pyrrole-2,5'-tetracyclo[5.5.2.0^{1,9}.0^{3,7}]tetradecan]-13'-ene-3,8'-dione

> <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      21.093   0.983   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      19.576   0.718   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      20.101  -0.730   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      19.579   2.258   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      18.246   3.030   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      16.911   2.262   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      15.579   3.034   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      14.244   2.266   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      14.242   0.726   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      15.574  -0.046   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      16.909   0.722   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      18.241  -0.050   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0      12.776   0.252   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0      12.298  -1.212   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0      11.873   1.500   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      10.898   0.269   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       9.334   0.613   0.000  0.00  0.00           C+0
HETATM   18  N   UNK     0       7.883   0.757   0.000  0.00  0.00           N+0
HETATM   19  C   UNK     0       7.984   2.161   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       9.159   3.156   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       6.525   2.297   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       4.996   2.729   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       3.977   1.541   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       4.919   0.287   0.000  0.00  0.00           C+0
HETATM   25  N   UNK     0       6.487   0.596   0.000  0.00  0.00           N+0
HETATM   26  C   UNK     0       7.910  -0.377   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0       7.916  -1.917   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0       7.925   3.295   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       9.363   2.321   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      10.908   2.733   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      10.633   4.248   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      12.040   3.777   0.000  0.00  0.00           C+0
HETATM   33  N   UNK     0      12.780   2.744   0.000  0.00  0.00           N+0
CONECT    1    2                                                            
CONECT    2    1    3    4   12                                             
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7   11                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   33                                                  
CONECT    9    8   10   13                                                  
CONECT   10    9   11                                                       
CONECT   11   10    6   12                                                  
CONECT   12   11    2                                                       
CONECT   13    9   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13   16   30   33                                             
CONECT   16   15   17                                                       
CONECT   17   16   18   26   29                                             
CONECT   18   17   19                                                       
CONECT   19   18   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19   22   25   28                                             
CONECT   22   21   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24   21   26                                                  
CONECT   26   25   17   27                                                  
CONECT   27   26                                                            
CONECT   28   21   29                                                       
CONECT   29   28   17   30                                                  
CONECT   30   29   15   31   32                                             
CONECT   31   30                                                            
CONECT   32   30                                                            
CONECT   33   15    8                                                       
MASTER        0    0    0    0    0    0    0    0   33    0   78    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₆H₂₉N₃O₄

Average Mass

447.5350 Da

Monoisotopic Mass

447.21581 Da

IUPAC Name

(1'S,2S,3'S,7'S)-13'-hydroxy-4',4',6,6-tetramethyl-3,6-dihydro-1H-9',14'-diazaspiro[chromeno[6,7-b]pyrrole-2,5'-tetracyclo[5.5.2.0^{1,9}.0^{3,7}]tetradecan]-13'-ene-3,8'-dione

Traditional Name

(1'S,2S,3'S,7'S)-13'-hydroxy-4',4',6,6-tetramethyl-1H-9',14'-diazaspiro[chromeno[6,7-b]pyrrole-2,5'-tetracyclo[5.5.2.0^{1,9}.0^{3,7}]tetradecan]-13'-ene-3,8'-dione

CAS Registry Number

Not Available

SMILES

CC1(C)[C@@H]2C[C@]34CCCN3C(=O)[C@@]2(C[C@]11NC2=C(C=C3OC(C)(C)C=CC3=C2)C1=O)N=C4O

InChI Identifier

InChI=1S/C26H29N3O4/c1-22(2)8-6-14-10-16-15(11-17(14)33-22)19(30)26(27-16)13-25-18(23(26,3)4)12-24(20(31)28-25)7-5-9-29(24)21(25)32/h6,8,10-11,18,27H,5,7,9,12-13H2,1-4H3,(H,28,31)/t18-,24-,25-,26+/m0/s1

InChI Key

VPZPMWLDKGSQNB-YCYYUTJKSA-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 ochraceus	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 2,2-dimethyl-1-benzopyrans. These are organic compounds containing a 1-benzopyran moiety that carries two methyl groups at the 2-position.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Benzopyrans

Sub Class

1-benzopyrans

Direct Parent

2,2-dimethyl-1-benzopyrans

Alternative Parents

Substituents

2,2-dimethyl-1-benzopyran
Alpha-amino acid or derivatives
Indolizidine
Dihydroindole
Indole or derivatives
Aryl alkyl ketone
Aryl ketone
Tetrahydropyridine
Secondary aliphatic/aromatic amine
Piperidinone
Delta-lactam
Alkyl aryl ether
Benzenoid
Piperidine
Vinylogous amide
Cyclic carboximidic acid
Tertiary carboxylic acid amide
Pyrrolidine
Lactam
Ketone
Carboxamide group
Amino acid or derivatives
Oxacycle
Azacycle
Organic 1,3-dipolar compound
Propargyl-type 1,3-dipolar organic compound
Secondary amine
Ether
Carboxylic acid derivative
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
Carbonyl group
Amine
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	3.29	ChemAxon
pKa (Strongest Acidic)	3.99	ChemAxon
pKa (Strongest Basic)	0.98	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	91.23 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	124.23 m³·mol⁻¹	ChemAxon
Polarizability	48.93 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

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

139584694

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (1's,2s,3's,7's)-13'-hydroxy-4',4',6,6-tetramethyl-1h-9',14'-diazaspiro[chromeno[6,7-b]pyrrole-2,5'-tetracyclo[5.5.2.0¹,⁹.0³,⁷]tetradecan]-13'-ene-3,8'-dione (NP0314543)

MOL for NP0314543 ((1's,2s,3's,7's)-13'-hydroxy-4',4',6,6-tetramethyl-1h-9',14'-diazaspiro[chromeno[6,7-b]pyrrole-2,5'-tetracyclo[5.5.2.0¹,⁹.0³,⁷]tetradecan]-13'-ene-3,8'-dione)

3D MOL for NP0314543 ((1's,2s,3's,7's)-13'-hydroxy-4',4',6,6-tetramethyl-1h-9',14'-diazaspiro[chromeno[6,7-b]pyrrole-2,5'-tetracyclo[5.5.2.0¹,⁹.0³,⁷]tetradecan]-13'-ene-3,8'-dione)

3D SDF for NP0314543 ((1's,2s,3's,7's)-13'-hydroxy-4',4',6,6-tetramethyl-1h-9',14'-diazaspiro[chromeno[6,7-b]pyrrole-2,5'-tetracyclo[5.5.2.0¹,⁹.0³,⁷]tetradecan]-13'-ene-3,8'-dione)

3D-SDF for NP0314543 ((1's,2s,3's,7's)-13'-hydroxy-4',4',6,6-tetramethyl-1h-9',14'-diazaspiro[chromeno[6,7-b]pyrrole-2,5'-tetracyclo[5.5.2.0¹,⁹.0³,⁷]tetradecan]-13'-ene-3,8'-dione)

PDB for NP0314543 ((1's,2s,3's,7's)-13'-hydroxy-4',4',6,6-tetramethyl-1h-9',14'-diazaspiro[chromeno[6,7-b]pyrrole-2,5'-tetracyclo[5.5.2.0¹,⁹.0³,⁷]tetradecan]-13'-ene-3,8'-dione)

3D PDB for NP0314543 ((1's,2s,3's,7's)-13'-hydroxy-4',4',6,6-tetramethyl-1h-9',14'-diazaspiro[chromeno[6,7-b]pyrrole-2,5'-tetracyclo[5.5.2.0¹,⁹.0³,⁷]tetradecan]-13'-ene-3,8'-dione)

SMILES for NP0314543 ((1's,2s,3's,7's)-13'-hydroxy-4',4',6,6-tetramethyl-1h-9',14'-diazaspiro[chromeno[6,7-b]pyrrole-2,5'-tetracyclo[5.5.2.0¹,⁹.0³,⁷]tetradecan]-13'-ene-3,8'-dione)

INCHI for NP0314543 ((1's,2s,3's,7's)-13'-hydroxy-4',4',6,6-tetramethyl-1h-9',14'-diazaspiro[chromeno[6,7-b]pyrrole-2,5'-tetracyclo[5.5.2.0¹,⁹.0³,⁷]tetradecan]-13'-ene-3,8'-dione)

Structure for NP0314543 ((1's,2s,3's,7's)-13'-hydroxy-4',4',6,6-tetramethyl-1h-9',14'-diazaspiro[chromeno[6,7-b]pyrrole-2,5'-tetracyclo[5.5.2.0¹,⁹.0³,⁷]tetradecan]-13'-ene-3,8'-dione)

3D Structure for NP0314543 ((1's,2s,3's,7's)-13'-hydroxy-4',4',6,6-tetramethyl-1h-9',14'-diazaspiro[chromeno[6,7-b]pyrrole-2,5'-tetracyclo[5.5.2.0¹,⁹.0³,⁷]tetradecan]-13'-ene-3,8'-dione)