MiMeDB: Showing metabocard for 7-(2-hydroxyethyl)-monascorubramine (MMDBc0005361)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2021-05-14 22:58:43 UTC

Update Date

2022-08-31 06:23:42 UTC

Metabolite ID

MMDBc0005361

Metabolite Identification

Common Name

7-(2-hydroxyethyl)-monascorubramine

Description

7-(2-hydroxyethyl)-monascorubramine belongs to the class of organic compounds known as annonaceous acetogenins. These are waxy derivatives of fatty acids (usually C32 or C34), containing a terminal carboxylic acid combined with a 2-propanol unit at the C-2 position to form a methyl- substituted alpha,beta-unsaturated-gamma-lactone. One of their interesting structural features is a single, adjacent, or nonadjacent tetrahydrofuran (THF) or tetrahydropyran (THP) system with one or two flanking hydroxyl group(s) at the center of a long hydrocarbon chain. 7-(2-hydroxyethyl)-monascorubramine is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL SDF PDB SMILES InChI


  Mrv1652305152100582D          

 33 35  0  0  0  0            999 V2000
   -6.2116    2.9427    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2776   -0.5313    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2948    3.8877    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4971    2.5302    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0846   -0.7029    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7826    2.9427    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0681    2.5302    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3537    2.9427    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6392    2.5302    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6367   -0.0898    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9247    2.9427    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7407    1.1364    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9957    0.3518    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5747    0.8664    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5128    1.8225    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6788    2.0926    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3198    1.6510    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3817    0.6949    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8718    2.2641    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2579    2.6071    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2103    2.5302    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4958    2.9427    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6169    3.0487    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4095    3.7632    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8099    3.2202    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9337    1.3079    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.4436   -0.2613    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2103    1.7052    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1689    3.6618    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0226    4.3152    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3974    3.9347    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3396   -1.4875    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1887    0.5233    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  4  1  1  0  0  0  0
  5  2  1  0  0  0  0
  6  4  1  0  0  0  0
  7  6  1  0  0  0  0
  8  7  1  0  0  0  0
  9  8  1  0  0  0  0
 10  5  2  0  0  0  0
 11  9  1  0  0  0  0
 13 12  1  0  0  0  0
 17 14  1  0  0  0  0
 17 15  2  0  0  0  0
 18 10  1  0  0  0  0
 18 14  2  0  0  0  0
 19 16  2  0  0  0  0
 19 17  1  0  0  0  0
 20 15  1  0  0  0  0
 21 11  1  0  0  0  0
 22 20  2  0  0  0  0
 22 21  1  0  0  0  0
 23 19  1  0  0  0  0
 24 22  1  0  0  0  0
 25  3  1  0  0  0  0
 25 20  1  0  0  0  0
 25 23  1  0  0  0  0
 26 12  1  0  0  0  0
 26 16  1  0  0  0  0
 26 18  1  0  0  0  0
 27 13  1  0  0  0  0
 28 21  2  0  0  0  0
 29 23  2  0  0  0  0
 30 24  2  0  0  0  0
 31 24  1  0  0  0  0
 31 25  1  0  0  0  0
 32  5  1  0  0  0  0
 33 10  1  0  0  0  0
M  END


  Mrv1652305152100582D          

 33 35  0  0  0  0            999 V2000
   -6.2116    2.9427    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2776   -0.5313    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2948    3.8877    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4971    2.5302    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0846   -0.7029    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7826    2.9427    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0681    2.5302    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3537    2.9427    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6392    2.5302    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6367   -0.0898    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9247    2.9427    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7407    1.1364    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9957    0.3518    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5747    0.8664    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5128    1.8225    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6788    2.0926    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3198    1.6510    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3817    0.6949    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8718    2.2641    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2579    2.6071    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2103    2.5302    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4958    2.9427    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6169    3.0487    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4095    3.7632    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8099    3.2202    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9337    1.3079    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.4436   -0.2613    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2103    1.7052    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1689    3.6618    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0226    4.3152    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3974    3.9347    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3396   -1.4875    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1887    0.5233    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  4  1  1  0  0  0  0
  5  2  1  0  0  0  0
  6  4  1  0  0  0  0
  7  6  1  0  0  0  0
  8  7  1  0  0  0  0
  9  8  1  0  0  0  0
 10  5  2  0  0  0  0
 11  9  1  0  0  0  0
 13 12  1  0  0  0  0
 17 14  1  0  0  0  0
 17 15  2  0  0  0  0
 18 10  1  0  0  0  0
 18 14  2  0  0  0  0
 19 16  2  0  0  0  0
 19 17  1  0  0  0  0
 20 15  1  0  0  0  0
 21 11  1  0  0  0  0
 22 20  2  0  0  0  0
 22 21  1  0  0  0  0
 23 19  1  0  0  0  0
 24 22  1  0  0  0  0
 25  3  1  0  0  0  0
 25 20  1  0  0  0  0
 25 23  1  0  0  0  0
 26 12  1  0  0  0  0
 26 16  1  0  0  0  0
 26 18  1  0  0  0  0
 27 13  1  0  0  0  0
 28 21  2  0  0  0  0
 29 23  2  0  0  0  0
 30 24  2  0  0  0  0
 31 24  1  0  0  0  0
 31 25  1  0  0  0  0
 32  5  1  0  0  0  0
 33 10  1  0  0  0  0
M  END
> <DATABASE_ID>
MMDBc0005361

> <DATABASE_NAME>
MIME

> <SMILES>
[H]C(C)=C([H])C1=CC2=CC3=C(C(=O)CCCCCCC)C(=O)OC3(C)C(=O)C2=CN1CCO

> <INCHI_IDENTIFIER>
InChI=1S/C25H31NO5/c1-4-6-7-8-9-11-21(28)22-20-15-17-14-18(10-5-2)26(12-13-27)16-19(17)23(29)25(20,3)31-24(22)30/h5,10,14-16,27H,4,6-9,11-13H2,1-3H3/b10-5-

> <INCHI_KEY>
NNVANSMEQBWXHJ-YHYXMXQVSA-N

> <FORMULA>
C25H31NO5

> <MOLECULAR_WEIGHT>
425.525

> <EXACT_MASS>
425.220223102

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
62

> <JCHEM_AVERAGE_POLARIZABILITY>
48.86341205473574

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
7-(2-hydroxyethyl)-9a-methyl-3-octanoyl-6-[(1Z)-prop-1-en-1-yl]-2H,7H,9H,9aH-furo[3,2-g]isoquinoline-2,9-dione

> <ALOGPS_LOGP>
3.92

> <JCHEM_LOGP>
3.9119081956666664

> <ALOGPS_LOGS>
-4.42

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
19.380928934377835

> <JCHEM_PKA_STRONGEST_ACIDIC>
15.565788325556337

> <JCHEM_PKA_STRONGEST_BASIC>
-2.5512951045378394

> <JCHEM_POLAR_SURFACE_AREA>
83.91000000000001

> <JCHEM_REFRACTIVITY>
123.74719999999995

> <JCHEM_ROTATABLE_BOND_COUNT>
10

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.63e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
7-(2-hydroxyethyl)-9a-methyl-3-octanoyl-6-[(1Z)-prop-1-en-1-yl]furo[3,2-g]isoquinoline-2,9-dione

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 15-MAY-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   15-MAY-21         0                                  
HETATM    1  C   UNK     0     -11.595   5.493   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.385  -0.992   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.417   7.257   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0     -10.261   4.723   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       3.891  -1.312   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -8.928   5.493   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -7.594   4.723   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -6.260   5.493   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -4.926   4.723   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.922  -0.168   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -3.593   5.493   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       6.983   2.121   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       7.459   0.657   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.940   1.617   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       0.957   3.402   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       5.000   3.906   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       2.464   3.082   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       4.446   1.297   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       3.494   4.226   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       0.481   4.867   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -2.259   4.723   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -0.925   5.493   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       3.018   5.691   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      -0.764   7.025   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       1.512   6.011   0.000  0.00  0.00           C+0
HETATM   26  N   UNK     0       5.476   2.442   0.000  0.00  0.00           N+0
HETATM   27  O   UNK     0       6.428  -0.488   0.000  0.00  0.00           O+0
HETATM   28  O   UNK     0      -2.259   3.183   0.000  0.00  0.00           O+0
HETATM   29  O   UNK     0       4.049   6.835   0.000  0.00  0.00           O+0
HETATM   30  O   UNK     0      -1.909   8.055   0.000  0.00  0.00           O+0
HETATM   31  O   UNK     0       0.742   7.345   0.000  0.00  0.00           O+0
HETATM   32  H   UNK     0       4.367  -2.777   0.000  0.00  0.00           H+0
HETATM   33  H   UNK     0       5.952   0.977   0.000  0.00  0.00           H+0
CONECT    1    4                                                            
CONECT    2    5                                                            
CONECT    3   25                                                            
CONECT    4    1    6                                                       
CONECT    5    2   10   32                                                  
CONECT    6    4    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   11                                                       
CONECT   10    5   18   33                                                  
CONECT   11    9   21                                                       
CONECT   12   13   26                                                       
CONECT   13   12   27                                                       
CONECT   14   17   18                                                       
CONECT   15   17   20                                                       
CONECT   16   19   26                                                       
CONECT   17   14   15   19                                                  
CONECT   18   10   14   26                                                  
CONECT   19   16   17   23                                                  
CONECT   20   15   22   25                                                  
CONECT   21   11   22   28                                                  
CONECT   22   20   21   24                                                  
CONECT   23   19   25   29                                                  
CONECT   24   22   30   31                                                  
CONECT   25    3   20   23   31                                             
CONECT   26   12   16   18                                                  
CONECT   27   13                                                            
CONECT   28   21                                                            
CONECT   29   23                                                            
CONECT   30   24                                                            
CONECT   31   24   25                                                       
CONECT   32    5                                                            
CONECT   33   10                                                            
MASTER        0    0    0    0    0    0    0    0   33    0   70    0
END

Synonyms

Not Available

Molecular Formula

C₂₅H₃₁NO₅

Average Mass

425.525

Monoisotopic Mass

425.220223102

IUPAC Name

7-(2-hydroxyethyl)-9a-methyl-3-octanoyl-6-[(1Z)-prop-1-en-1-yl]-2H,7H,9H,9aH-furo[3,2-g]isoquinoline-2,9-dione

Traditional Name

7-(2-hydroxyethyl)-9a-methyl-3-octanoyl-6-[(1Z)-prop-1-en-1-yl]furo[3,2-g]isoquinoline-2,9-dione

CAS Registry Number

Not Available

SMILES

[H]C(C)=C([H])C1=CC2=CC3=C(C(=O)CCCCCCC)C(=O)OC3(C)C(=O)C2=CN1CCO

InChI Identifier

InChI=1S/C25H31NO5/c1-4-6-7-8-9-11-21(28)22-20-15-17-14-18(10-5-2)26(12-13-27)16-19(17)23(29)25(20,3)31-24(22)30/h5,10,14-16,27H,4,6-9,11-13H2,1-3H3/b10-5-

InChI Key

NNVANSMEQBWXHJ-YHYXMXQVSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as annonaceous acetogenins. These are waxy derivatives of fatty acids (usually C32 or C34), containing a terminal carboxylic acid combined with a 2-propanol unit at the C-2 position to form a methyl- substituted alpha,beta-unsaturated-gamma-lactone. One of their interesting structural features is a single, adjacent, or nonadjacent tetrahydrofuran (THF) or tetrahydropyran (THP) system with one or two flanking hydroxyl group(s) at the center of a long hydrocarbon chain.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Fatty alcohols

Direct Parent

Annonaceous acetogenins

Alternative Parents

Substituents

Annonaceae acetogenin skeleton
Aryl ketone
Aryl alkyl ketone
Alpha-acyloxy ketone
2-furanone
Pyridine
Dihydrofuran
Enoate ester
Heteroaromatic compound
Alpha,beta-unsaturated carboxylic ester
Vinylogous amide
Carboxylic acid ester
Ketone
Lactone
Organoheterocyclic compound
Azacycle
Oxacycle
Carboxylic acid derivative
Alkanolamine
Monocarboxylic acid or derivatives
Hydrocarbon derivative
Organonitrogen compound
Organopnictogen compound
Alcohol
Organooxygen compound
Carbonyl group
Organic oxygen compound
Organic nitrogen compound
Primary alcohol
Organic oxide
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

Not Available

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Property	Value	Source
Water Solubility	0.016 g/L	ALOGPS
logP	3.92	ALOGPS
logP	3.91	ChemAxon
logS	-4.4	ALOGPS
pKa (Strongest Acidic)	15.57	ChemAxon
pKa (Strongest Basic)	-2.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	83.91 Å²	ChemAxon
Rotatable Bond Count	10	ChemAxon
Refractivity	123.75 m³·mol⁻¹	ChemAxon
Polarizability	48.86 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Spectra

Not Available

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Associated OMIM IDs

114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)

Human Proteins and Enzymes

Protein ID	Protein Name	Protein Type	Uniprot ID	Species

Human Pathways

Pathways

Name	SMPDB/PathBank

Metabolic Reactions

Not Available

Health Effects and Bioactivity

Health Outcome/Bioactivity	Metabolite Response/Effect	Evidence Type	Host and Biospecimen	Data Source	Reference

Microbial Sources

Superkingdom/Kingdom	Phylum	Total species	Hosts and Body Sites	Microbial Links
Eukaryota/Fungi	Ascomycota	1	Human feces	Metabolic reconstruction

Exposure Sources

Source Type	Source Sub-type	Species	Data Source	Reference

Host Biospecimen and Location

Host and Biospecimen	Status	Mean	Std	Min	Max	Units	Age	Sex	Health Condition	Data Source	Reference

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

78434708

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

139584399

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

General References

van Santen JA, Poynton EF, Iskakova D, McMann E, Alsup TA, Clark TN, Fergusson CH, Fewer DP, Hughes AH, McCadden CA, Parra J, Soldatou S, Rudolf JD, Janssen EM, Duncan KR, Linington RG: The Natural Products Atlas 2.0: a database of microbially-derived natural products. Nucleic Acids Res. 2022 Jan 7;50(D1):D1317-D1323. doi: 10.1093/nar/gkab941. [PubMed:34718710 ]

Showing metabocard for 7-(2-hydroxyethyl)-monascorubramine (MMDBc0005361)

MOL for #<Metabolite:0x00007f47058166d8>

3D MOL for #<Metabolite:0x00007f47058166d8>

3D SDF for #<Metabolite:0x00007f47058166d8>

3D-SDF for #<Metabolite:0x00007f47058166d8>

PDB for #<Metabolite:0x00007f47058166d8>

3D PDB for #<Metabolite:0x00007f47058166d8>

SMILES for #<Metabolite:0x00007f47058166d8>

INCHI for #<Metabolite:0x00007f47058166d8>

Structure for #<Metabolite:0x00007f47058166d8>

3D Structure for #<Metabolite:0x00007f47058166d8>