MiMeDB: Showing metabocard for Sequoiatone B (MMDBc0002211)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2021-05-14 20:41:11 UTC

Update Date

2022-08-31 06:19:03 UTC

Metabolite ID

MMDBc0002211

Metabolite Identification

Common Name

Sequoiatone B

Description

Sequoiatone B belongs to the class of organic compounds known as pyrans. Pyrans are compounds containing a pyran ring, which is a six-member heterocyclic, non-aromatic ring with five carbon atoms, one oxygen atom and two ring double bonds. Based on a literature review very few articles have been published on Sequoiatone B.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652305142122412D          

 29 30  0  0  1  0            999 V2000
   -0.9920    7.4340    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2948    6.6090    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8064    8.8385    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4382    9.4874    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3196    5.6420    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2775    7.8465    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4369    7.4340    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1514    7.8465    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8659    7.4340    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5803    7.8465    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5689    8.1240    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7238    7.4340    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7439    9.5530    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2948    7.4340    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    7.9814    8.8385    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7439    8.1240    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4382    7.8465    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3314    8.8385    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0093    7.8465    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1919    7.5109    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3634    6.7039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5245    8.6670    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.0093    8.6715    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7503    6.1519    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6995    8.6670    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1481    6.4490    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.5689    9.5530    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7238    6.6090    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5803    7.0215    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  6  1  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  9  1  0  0  0  0
 14  2  1  6  0  0  0
 14 10  1  0  0  0  0
 15  3  1  0  0  0  0
 15 11  2  0  0  0  0
 16 11  1  0  0  0  0
 17 12  2  0  0  0  0
 18 13  2  0  0  0  0
 18 16  1  0  0  0  0
 19 12  1  0  0  0  0
 19 14  1  0  0  0  0
 20 16  2  0  0  0  0
 20 17  1  0  0  0  0
 21 20  1  0  0  0  0
 22  4  1  1  0  0  0
 22 17  1  0  0  0  0
 22 18  1  0  0  0  0
 23 19  2  0  0  0  0
 24 21  2  0  0  0  0
 22 25  1  6  0  0  0
 26  5  1  0  0  0  0
 26 21  1  0  0  0  0
 27 13  1  0  0  0  0
 27 15  1  0  0  0  0
 28 12  1  0  0  0  0
 14 29  1  1  0  0  0
M  END


  Mrv1652305142122412D          

 29 30  0  0  1  0            999 V2000
   -0.9920    7.4340    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2948    6.6090    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8064    8.8385    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4382    9.4874    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3196    5.6420    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2775    7.8465    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4369    7.4340    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1514    7.8465    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8659    7.4340    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5803    7.8465    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5689    8.1240    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7238    7.4340    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7439    9.5530    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2948    7.4340    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    7.9814    8.8385    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7439    8.1240    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4382    7.8465    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3314    8.8385    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0093    7.8465    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1919    7.5109    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3634    6.7039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5245    8.6670    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.0093    8.6715    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7503    6.1519    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6995    8.6670    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1481    6.4490    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.5689    9.5530    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7238    6.6090    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5803    7.0215    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  6  1  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  9  1  0  0  0  0
 14  2  1  6  0  0  0
 14 10  1  0  0  0  0
 15  3  1  0  0  0  0
 15 11  2  0  0  0  0
 16 11  1  0  0  0  0
 17 12  2  0  0  0  0
 18 13  2  0  0  0  0
 18 16  1  0  0  0  0
 19 12  1  0  0  0  0
 19 14  1  0  0  0  0
 20 16  2  0  0  0  0
 20 17  1  0  0  0  0
 21 20  1  0  0  0  0
 22  4  1  1  0  0  0
 22 17  1  0  0  0  0
 22 18  1  0  0  0  0
 23 19  2  0  0  0  0
 24 21  2  0  0  0  0
 22 25  1  6  0  0  0
 26  5  1  0  0  0  0
 26 21  1  0  0  0  0
 27 13  1  0  0  0  0
 27 15  1  0  0  0  0
 28 12  1  0  0  0  0
 14 29  1  1  0  0  0
M  END
> <DATABASE_ID>
MMDBc0002211

> <DATABASE_NAME>
MIME

> <SMILES>
[H]\C(C(=O)[C@]([H])(C)CCCCCC)=C1/C(C(=O)OC)=C2C=C(C)OC=C2[C@@]1(C)O

> <INCHI_IDENTIFIER>
InChI=1S/C22H30O5/c1-6-7-8-9-10-14(2)19(23)12-17-20(21(24)26-5)16-11-15(3)27-13-18(16)22(17,4)25/h11-14,25H,6-10H2,1-5H3/b17-12-/t14-,22+/m1/s1

> <INCHI_KEY>
AZRKTTNHSKOLMR-ZFKUNJMVSA-N

> <FORMULA>
C22H30O5

> <MOLECULAR_WEIGHT>
374.477

> <EXACT_MASS>
374.209324066

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
57

> <JCHEM_AVERAGE_POLARIZABILITY>
42.82807070397581

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
methyl (6Z,7S)-7-hydroxy-3,7-dimethyl-6-[(3R)-3-methyl-2-oxononylidene]-6H,7H-cyclopenta[c]pyran-5-carboxylate

> <ALOGPS_LOGP>
4.29

> <JCHEM_LOGP>
3.3583136379999994

> <ALOGPS_LOGS>
-4.83

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.538116265053873

> <JCHEM_PKA_STRONGEST_BASIC>
-3.438227945665435

> <JCHEM_POLAR_SURFACE_AREA>
72.83000000000001

> <JCHEM_REFRACTIVITY>
107.80639999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
9

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.50e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
methyl (6Z,7S)-7-hydroxy-3,7-dimethyl-6-[(3R)-3-methyl-2-oxononylidene]cyclopenta[c]pyran-5-carboxylate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 14-MAY-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   14-MAY-21         0                                  
HETATM    1  C   UNK     0      -1.852  13.877   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       6.150  12.337   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      16.439  16.499   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      10.151  17.710   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      13.663  10.532   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -0.518  14.647   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.816  13.877   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.149  14.647   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       3.483  13.877   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.817  14.647   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      14.129  15.165   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       8.818  13.877   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      12.589  17.832   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       6.150  13.877   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      14.899  16.499   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      12.589  15.165   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      10.151  14.647   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      11.819  16.499   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       7.484  14.647   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      11.558  14.020   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      11.878  12.514   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      10.312  16.178   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       7.484  16.187   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0      10.734  11.484   0.000  0.00  0.00           O+0
HETATM   25  O   UNK     0       8.772  16.178   0.000  0.00  0.00           O+0
HETATM   26  O   UNK     0      13.343  12.038   0.000  0.00  0.00           O+0
HETATM   27  O   UNK     0      14.129  17.832   0.000  0.00  0.00           O+0
HETATM   28  H   UNK     0       8.818  12.337   0.000  0.00  0.00           H+0
HETATM   29  H   UNK     0       4.817  13.107   0.000  0.00  0.00           H+0
CONECT    1    6                                                            
CONECT    2   14                                                            
CONECT    3   15                                                            
CONECT    4   22                                                            
CONECT    5   26                                                            
CONECT    6    1    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   14                                                       
CONECT   11   15   16                                                       
CONECT   12   17   19   28                                                  
CONECT   13   18   27                                                       
CONECT   14    2   10   19   29                                             
CONECT   15    3   11   27                                                  
CONECT   16   11   18   20                                                  
CONECT   17   12   20   22                                                  
CONECT   18   13   16   22                                                  
CONECT   19   12   14   23                                                  
CONECT   20   16   17   21                                                  
CONECT   21   20   24   26                                                  
CONECT   22    4   17   18   25                                             
CONECT   23   19                                                            
CONECT   24   21                                                            
CONECT   25   22                                                            
CONECT   26    5   21                                                       
CONECT   27   13   15                                                       
CONECT   28   12                                                            
CONECT   29   14                                                            
MASTER        0    0    0    0    0    0    0    0   29    0   60    0
END

Synonyms

Not Available

Molecular Formula

C₂₂H₃₀O₅

Average Mass

374.477

Monoisotopic Mass

374.209324066

IUPAC Name

methyl (6Z,7S)-7-hydroxy-3,7-dimethyl-6-[(3R)-3-methyl-2-oxononylidene]-6H,7H-cyclopenta[c]pyran-5-carboxylate

Traditional Name

methyl (6Z,7S)-7-hydroxy-3,7-dimethyl-6-[(3R)-3-methyl-2-oxononylidene]cyclopenta[c]pyran-5-carboxylate

CAS Registry Number

Not Available

SMILES

[H]\C(C(=O)[C@]([H])(C)CCCCCC)=C1/C(C(=O)OC)=C2C=C(C)OC=C2[C@@]1(C)O

InChI Identifier

InChI=1S/C22H30O5/c1-6-7-8-9-10-14(2)19(23)12-17-20(21(24)26-5)16-11-15(3)27-13-18(16)22(17,4)25/h11-14,25H,6-10H2,1-5H3/b17-12-/t14-,22+/m1/s1

InChI Key

AZRKTTNHSKOLMR-ZFKUNJMVSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as pyrans. Pyrans are compounds containing a pyran ring, which is a six-member heterocyclic, non-aromatic ring with five carbon atoms, one oxygen atom and two ring double bonds.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Pyrans

Sub Class

Not Available

Direct Parent

Pyrans

Alternative Parents

Substituents

Pyran
Acryloyl-group
Enone
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Methyl ester
Tertiary alcohol
Carboxylic acid ester
Ketone
Carboxylic acid derivative
Oxacycle
Monocarboxylic acid or derivatives
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Carbonyl group
Alcohol
Organooxygen compound
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	0.0055 g/L	ALOGPS
logP	4.29	ALOGPS
logP	3.36	ChemAxon
logS	-4.8	ALOGPS
pKa (Strongest Acidic)	13.54	ChemAxon
pKa (Strongest Basic)	-3.4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	72.83 Å²	ChemAxon
Rotatable Bond Count	9	ChemAxon
Refractivity	107.81 m³·mol⁻¹	ChemAxon
Polarizability	42.83 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	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	3	Human feces	Metabolic reconstruction

Exposure Sources

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

78436401

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

139583483

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 Sequoiatone B (MMDBc0002211)

MOL for #<Metabolite:0x0000556b6afc6248>

3D MOL for #<Metabolite:0x0000556b6afc6248>

3D SDF for #<Metabolite:0x0000556b6afc6248>

3D-SDF for #<Metabolite:0x0000556b6afc6248>

PDB for #<Metabolite:0x0000556b6afc6248>

3D PDB for #<Metabolite:0x0000556b6afc6248>

SMILES for #<Metabolite:0x0000556b6afc6248>

INCHI for #<Metabolite:0x0000556b6afc6248>

Structure for #<Metabolite:0x0000556b6afc6248>

3D Structure for #<Metabolite:0x0000556b6afc6248>