NP-MRD: Showing NP-Card for Fumitremorgin B (NP0058010)

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Record Information

Version

2.0

Created at

2022-04-28 03:20:49 UTC

Updated at

2022-04-28 03:20:49 UTC

NP-MRD ID

NP0058010

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Fumitremorgin B

Description

Fumitremorgin B, also known as lanosulin, belongs to the class of organic compounds known as beta carbolines. Beta carbolines are compounds containing a 9H-pyrido[3,4-b]indole moiety. Fumitremorgin B is found in Aspergillus caespitosus, Aspergillus fumigatus, Neosartaria fischeri, Penicillium janthinellum, Penicillium lanosum, Penicillium melinii, Penicillium piscarium and Talaromyces verruculosus. Fumitremorgin B was first documented in 2018 (PMID: 30306990). Based on a literature review a small amount of articles have been published on fumitremorgin B (PMID: 30837981) (PMID: 34796596) (PMID: 31580360) (PMID: 31117657).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304282205202D          

 35 39  0  0  1  0            999 V2000
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M  END

     RDKit          3D

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M  END


  Mrv1652304282205202D          

 35 39  0  0  1  0            999 V2000
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M  END
> <DATABASE_ID>
NP0058010

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC=C2C(=C1)N(CC=C(C)C)C1=C2[C@H](O)[C@]2(O)N([C@H]1C=C(C)C)C(=O)[C@@H]1CCCN1C2=O

> <INCHI_IDENTIFIER>
InChI=1S/C27H33N3O5/c1-15(2)10-12-28-20-14-17(35-5)8-9-18(20)22-23(28)21(13-16(3)4)30-25(32)19-7-6-11-29(19)26(33)27(30,34)24(22)31/h8-10,13-14,19,21,24,31,34H,6-7,11-12H2,1-5H3/t19-,21-,24-,27+/m0/s1

> <INCHI_KEY>
WEIYXEFMCIRZHC-MWGWWEMPSA-N

> <FORMULA>
C27H33N3O5

> <MOLECULAR_WEIGHT>
479.577

> <EXACT_MASS>
479.242021175

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
68

> <JCHEM_AVERAGE_POLARIZABILITY>
53.049018573247174

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1R,2S,12S,15S)-1,2-dihydroxy-7-methoxy-10-(3-methylbut-2-en-1-yl)-12-(2-methylprop-1-en-1-yl)-10,13,19-triazapentacyclo[11.7.0.0^{3,11}.0^{4,9}.0^{15,19}]icosa-3(11),4(9),5,7-tetraene-14,20-dione

> <ALOGPS_LOGP>
2.16

> <JCHEM_LOGP>
2.7413935126666678

> <ALOGPS_LOGS>
-3.21

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.535161709948355

> <JCHEM_PKA_STRONGEST_ACIDIC>
10.13049435801047

> <JCHEM_PKA_STRONGEST_BASIC>
-3.7926145897706016

> <JCHEM_POLAR_SURFACE_AREA>
95.24000000000001

> <JCHEM_REFRACTIVITY>
133.33460000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.99e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1R,2S,12S,15S)-1,2-dihydroxy-7-methoxy-10-(3-methylbut-2-en-1-yl)-12-(2-methylprop-1-en-1-yl)-10,13,19-triazapentacyclo[11.7.0.0^{3,11}.0^{4,9}.0^{15,19}]icosa-3(11),4(9),5,7-tetraene-14,20-dione

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 28-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   28-APR-22         0                                  
HETATM    1  C   UNK     0      12.737   4.209   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      11.198   4.141   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      10.487   2.775   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      11.315   1.477   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      12.854   1.544   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      13.564   2.911   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      15.103   2.978   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0      15.931   1.680   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       8.968   3.029   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       8.740   4.552   0.000  0.00  0.00           C+0
HETATM   11  N   UNK     0      10.118   5.239   0.000  0.00  0.00           N+0
HETATM   12  C   UNK     0      10.372   6.758   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      11.814   7.298   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      12.068   8.817   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      13.510   9.357   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      10.879   9.796   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       7.307   5.116   0.000  0.00  0.00           C+0
HETATM   18  N   UNK     0       6.102   4.157   0.000  0.00  0.00           N+0
HETATM   19  C   UNK     0       6.331   2.634   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       7.764   2.070   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       7.992   0.547   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       5.126   1.674   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       5.354   0.151   0.000  0.00  0.00           O+0
HETATM   24  N   UNK     0       3.693   2.238   0.000  0.00  0.00           N+0
HETATM   25  C   UNK     0       3.464   3.761   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       4.669   4.720   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0       4.441   6.243   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0       1.945   4.015   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       1.235   2.649   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       2.315   1.551   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0       6.559   1.111   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0       7.079   6.639   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       8.284   7.598   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       9.717   7.034   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       8.056   9.121   0.000  0.00  0.00           C+0
CONECT    1    2    6                                                       
CONECT    2    1    3   11                                                  
CONECT    3    2    4    9                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    1    7                                                  
CONECT    7    6    8                                                       
CONECT    8    7                                                            
CONECT    9    3   10   20                                                  
CONECT   10    9   11   17                                                  
CONECT   11   10    2   12                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14                                                            
CONECT   17   10   18   32                                                  
CONECT   18   17   19   26                                                  
CONECT   19   18   20   22   31                                             
CONECT   20   19    9   21                                                  
CONECT   21   20                                                            
CONECT   22   19   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22   25   30                                                  
CONECT   25   24   26   28                                                  
CONECT   26   25   18   27                                                  
CONECT   27   26                                                            
CONECT   28   25   29                                                       
CONECT   29   28   30                                                       
CONECT   30   29   24                                                       
CONECT   31   19                                                            
CONECT   32   17   33                                                       
CONECT   33   32   34   35                                                  
CONECT   34   33                                                            
CONECT   35   33                                                            
MASTER        0    0    0    0    0    0    0    0   35    0   78    0
END

View in JSmol

Synonyms

Value	Source
Lanosulin	ChEBI

Chemical Formula

C₂₇H₃₃N₃O₅

Average Mass

479.5770 Da

Monoisotopic Mass

479.24202 Da

IUPAC Name

(1R,2S,12S,15S)-1,2-dihydroxy-7-methoxy-10-(3-methylbut-2-en-1-yl)-12-(2-methylprop-1-en-1-yl)-10,13,19-triazapentacyclo[11.7.0.0^{3,11}.0^{4,9}.0^{15,19}]icosa-3(11),4(9),5,7-tetraene-14,20-dione

Traditional Name

(1R,2S,12S,15S)-1,2-dihydroxy-7-methoxy-10-(3-methylbut-2-en-1-yl)-12-(2-methylprop-1-en-1-yl)-10,13,19-triazapentacyclo[11.7.0.0^{3,11}.0^{4,9}.0^{15,19}]icosa-3(11),4(9),5,7-tetraene-14,20-dione

CAS Registry Number

Not Available

SMILES

COC1=CC=C2C(=C1)N(CC=C(C)C)C1=C2[C@H](O)[C@]2(O)N([C@H]1C=C(C)C)C(=O)[C@@H]1CCCN1C2=O

InChI Identifier

InChI=1S/C27H33N3O5/c1-15(2)10-12-28-20-14-17(35-5)8-9-18(20)22-23(28)21(13-16(3)4)30-25(32)19-7-6-11-29(19)26(33)27(30,34)24(22)31/h8-10,13-14,19,21,24,31,34H,6-7,11-12H2,1-5H3/t19-,21-,24-,27+/m0/s1

InChI Key

WEIYXEFMCIRZHC-MWGWWEMPSA-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, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, 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 caespitosus	Fungi	KNApSAcK
Aspergillus fumigatus	Fungi	KNApSAcK
Neosartaria fischeri	-	KNApSAcK
Penicillium janthinellum	Fungi	KNApSAcK
Penicillium lanosum	Fungi	KNApSAcK
Penicillium melinii	LOTUS Database	35616633
Penicillium piscarium	Fungi	KNApSAcK
Talaromyces verruculosus	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as beta carbolines. Beta carbolines are compounds containing a 9H-pyrido[3,4-b]indole moiety.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Indoles and derivatives

Sub Class

Pyridoindoles

Direct Parent

Beta carbolines

Alternative Parents

Substituents

Beta-carboline
Alpha-amino acid or derivatives
N-alkylindole
3-alkylindole
Indole
Anisole
Dioxopiperazine
2,5-dioxopiperazine
Alkyl aryl ether
N-alkylpiperazine
1,4-diazinane
Piperazine
Substituted pyrrole
Benzenoid
Pyrrolidine
Pyrrole
Tertiary carboxylic acid amide
Heteroaromatic compound
Secondary alcohol
Lactam
Carboxamide group
Alkanolamine
Azacycle
Ether
Carboxylic acid derivative
Organic oxygen compound
Alcohol
Hydrocarbon derivative
Carbonyl group
Organic oxide
Organopnictogen compound
Organic nitrogen compound
Organonitrogen compound
Organooxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

organic heteropentacyclic compound (CHEBI:64531 )
indole alkaloid (CHEBI:64531 )

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	2.16	ALOGPS
logP	2.74	ChemAxon
logS	-3.2	ALOGPS
pKa (Strongest Acidic)	10.13	ChemAxon
pKa (Strongest Basic)	-3.8	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	95.24 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	133.33 m³·mol⁻¹	ChemAxon
Polarizability	53.05 Å³	ChemAxon
Number of Rings	5	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

C00011297

Chemspider ID

94836

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

105113

PDB ID

Not Available

ChEBI ID

64531

Good Scents ID

Not Available

References

General References

Knowles SL, Raja HA, Wright AJ, Lee AML, Caesar LK, Cech NB, Mead ME, Steenwyk JL, Ries LNA, Goldman GH, Rokas A, Oberlies NH: Mapping the Fungal Battlefield: Using in situ Chemistry and Deletion Mutants to Monitor Interspecific Chemical Interactions Between Fungi. Front Microbiol. 2019 Feb 19;10:285. doi: 10.3389/fmicb.2019.00285. eCollection 2019. [PubMed:30837981 ]
Wu L, Wang Z, Cen Y, Wang B, Zhou J: Structural Insight into the Catalytic Mechanism of the Endoperoxide Synthase FtmOx1. Angew Chem Int Ed Engl. 2022 Mar 14;61(12):e202112063. doi: 10.1002/anie.202112063. Epub 2022 Feb 3. [PubMed:34796596 ]
Milaczewska A, Borowski T: On the reaction mechanism of an endoperoxide ring formation by fumitremorgin B endoperoxidase. The right arrangement makes a difference. Dalton Trans. 2019 Nov 21;48(43):16211-16221. doi: 10.1039/c9dt02581b. Epub 2019 Oct 3. [PubMed:31580360 ]
Dunham NP, Del Rio Pantoja JM, Zhang B, Rajakovich LJ, Allen BD, Krebs C, Boal AK, Bollinger JM Jr: Hydrogen Donation but not Abstraction by a Tyrosine (Y68) during Endoperoxide Installation by Verruculogen Synthase (FtmOx1). J Am Chem Soc. 2019 Jun 26;141(25):9964-9979. doi: 10.1021/jacs.9b03567. Epub 2019 Jun 12. [PubMed:31117657 ]
Ji JN, Chen SL: Asymmetric abstraction of two chemically-equivalent methylene hydrogens: significant enantioselectivity of endoperoxide presented by fumitremorgin B endoperoxidase. Phys Chem Chem Phys. 2018 Nov 7;20(41):26500-26505. doi: 10.1039/c8cp05637d. Epub 2018 Oct 11. [PubMed:30306990 ]

Showing NP-Card for Fumitremorgin B (NP0058010)

MOL for NP0058010 (Fumitremorgin B)

3D MOL for NP0058010 (Fumitremorgin B)

3D SDF for NP0058010 (Fumitremorgin B)

3D-SDF for NP0058010 (Fumitremorgin B)

PDB for NP0058010 (Fumitremorgin B)

3D PDB for NP0058010 (Fumitremorgin B)

SMILES for NP0058010 (Fumitremorgin B)

INCHI for NP0058010 (Fumitremorgin B)

Structure for NP0058010 (Fumitremorgin B)

3D Structure for NP0058010 (Fumitremorgin B)