NP-MRD: Showing NP-Card for terrein (NP0036622)

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Record Information

Version

2.0

Created at

2021-06-20 19:44:48 UTC

Updated at

2021-06-30 00:08:22 UTC

NP-MRD ID

NP0036622

Secondary Accession Numbers

None

Natural Product Identification

Common Name

terrein

Provided By

JEOL Database JEOL Logo

Description

Terrein belongs to the class of organic compounds known as 1,2-diols. These are polyols containing an alcohol group at two adjacent positions. terrein is found in Emericella variecolor and Aspergillus terreus. terrein was first documented in 2020 (PMID: 33195942). Based on a literature review a small amount of articles have been published on Terrein (PMID: 34114710) (PMID: 33846818) (PMID: 33533162).

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306202121443D          

 21 21  0  0  0  0            999 V2000
   -0.8158   -1.7187    1.5100 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9270   -0.2295    1.4158 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0410    0.5395    0.7639 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0930    1.9818    0.6488 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9101    2.6949    0.1224 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5339    4.1066    0.2553 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2703    5.0210   -0.0908 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7977    4.2831    0.9462 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.6139    4.9328    2.1994 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2596    2.8261    1.1078 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.3759    2.5850    0.2483 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7064   -2.1857    1.0786 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0617   -2.1046    0.9817 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7425   -2.0205    2.5593 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7778    0.2034    1.9357 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8119    0.0555    0.2861 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8531    2.3682   -0.2788 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4764    4.8711    0.3202 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1665    5.7772    1.9988 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5511    2.6117    2.1414 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5000    1.6219    0.1963 H   0  0  0  0  0  0  0  0  0  0  0  0
  4 10  1  0  0  0  0
  6  7  2  0  0  0  0
  4  3  1  0  0  0  0
 10  8  1  0  0  0  0
  3  2  2  0  0  0  0
  8  6  1  0  0  0  0
  2  1  1  0  0  0  0
  6  5  1  0  0  0  0
  8  9  1  0  0  0  0
  5  4  2  0  0  0  0
 10 11  1  0  0  0  0
 10 20  1  1  0  0  0
  8 18  1  6  0  0  0
  5 17  1  0  0  0  0
  3 16  1  0  0  0  0
  2 15  1  0  0  0  0
  1 12  1  0  0  0  0
  1 13  1  0  0  0  0
  1 14  1  0  0  0  0
  9 19  1  0  0  0  0
 11 21  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0036622

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]O[C@@]1([H])C(=O)C([H])=C(\C([H])=C(/[H])C([H])([H])[H])[C@]1([H])O[H]

> <INCHI_IDENTIFIER>
InChI=1S/C8H10O3/c1-2-3-5-4-6(9)8(11)7(5)10/h2-4,7-8,10-11H,1H3/b3-2+/t7-,8-/m0/s1

> <INCHI_KEY>
MHOOPNKRBMHHEC-HZIBQTDNSA-N

> <FORMULA>
C8H10O3

> <MOLECULAR_WEIGHT>
154.165

> <EXACT_MASS>
154.062994182

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
21

> <JCHEM_AVERAGE_POLARIZABILITY>
15.812798189330781

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(4S,5R)-4,5-dihydroxy-3-[(1E)-prop-1-en-1-yl]cyclopent-2-en-1-one

> <ALOGPS_LOGP>
-0.13

> <JCHEM_LOGP>
0.021963966666666473

> <ALOGPS_LOGS>
-0.22

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.211256114862422

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.311488205100407

> <JCHEM_PKA_STRONGEST_BASIC>
-3.5228885354846042

> <JCHEM_POLAR_SURFACE_AREA>
57.53

> <JCHEM_REFRACTIVITY>
42.04

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
9.32e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(4S,5R)-4,5-dihydroxy-3-[(1E)-prop-1-en-1-yl]cyclopent-2-en-1-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 20-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   20-JUN-21         0                                  
HETATM    1  C   UNK     0      -0.816  -1.719   1.510  0.00  0.00           C+0
HETATM    2  C   UNK     0      -0.927  -0.230   1.416  0.00  0.00           C+0
HETATM    3  C   UNK     0      -0.041   0.540   0.764  0.00  0.00           C+0
HETATM    4  C   UNK     0      -0.093   1.982   0.649  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.910   2.695   0.122  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.534   4.107   0.255  0.00  0.00           C+0
HETATM    7  O   UNK     0       1.270   5.021  -0.091  0.00  0.00           O+0
HETATM    8  C   UNK     0      -0.798   4.283   0.946  0.00  0.00           C+0
HETATM    9  O   UNK     0      -0.614   4.933   2.199  0.00  0.00           O+0
HETATM   10  C   UNK     0      -1.260   2.826   1.108  0.00  0.00           C+0
HETATM   11  O   UNK     0      -2.376   2.585   0.248  0.00  0.00           O+0
HETATM   12  H   UNK     0      -1.706  -2.186   1.079  0.00  0.00           H+0
HETATM   13  H   UNK     0       0.062  -2.105   0.982  0.00  0.00           H+0
HETATM   14  H   UNK     0      -0.743  -2.021   2.559  0.00  0.00           H+0
HETATM   15  H   UNK     0      -1.778   0.203   1.936  0.00  0.00           H+0
HETATM   16  H   UNK     0       0.812   0.056   0.286  0.00  0.00           H+0
HETATM   17  H   UNK     0       1.853   2.368  -0.279  0.00  0.00           H+0
HETATM   18  H   UNK     0      -1.476   4.871   0.320  0.00  0.00           H+0
HETATM   19  H   UNK     0      -0.167   5.777   1.999  0.00  0.00           H+0
HETATM   20  H   UNK     0      -1.551   2.612   2.141  0.00  0.00           H+0
HETATM   21  H   UNK     0      -2.500   1.622   0.196  0.00  0.00           H+0
CONECT    1    2   12   13   14                                             
CONECT    2    3    1   15                                                  
CONECT    3    4    2   16                                                  
CONECT    4   10    3    5                                                  
CONECT    5    6    4   17                                                  
CONECT    6    7    8    5                                                  
CONECT    7    6                                                            
CONECT    8   10    6    9   18                                             
CONECT    9    8   19                                                       
CONECT   10    4    8   11   20                                             
CONECT   11   10   21                                                       
CONECT   12    1                                                            
CONECT   13    1                                                            
CONECT   14    1                                                            
CONECT   15    2                                                            
CONECT   16    3                                                            
CONECT   17    5                                                            
CONECT   18    8                                                            
CONECT   19    9                                                            
CONECT   20   10                                                            
CONECT   21   11                                                            
MASTER        0    0    0    0    0    0    0    0   21    0   42    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₈H₁₀O₃

Average Mass

154.1650 Da

Monoisotopic Mass

154.06299 Da

IUPAC Name

(4S,5R)-4,5-dihydroxy-3-[(1E)-prop-1-en-1-yl]cyclopent-2-en-1-one

Traditional Name

(4S,5R)-4,5-dihydroxy-3-[(1E)-prop-1-en-1-yl]cyclopent-2-en-1-one

CAS Registry Number

Not Available

SMILES

[H]O[C@@]1([H])C(=O)C([H])=C(\C([H])=C(/[H])C([H])([H])[H])[C@]1([H])O[H]

InChI Identifier

InChI=1S/C8H10O3/c1-2-3-5-4-6(9)8(11)7(5)10/h2-4,7-8,10-11H,1H3/b3-2+/t7-,8-/m0/s1

InChI Key

MHOOPNKRBMHHEC-HZIBQTDNSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Aspergillus stellatus	-	KNApSAcK
Aspergillus terreus	JEOL database	Liao, W. -Y., et al, J. Nat. Prod. 75, 630 (2012)

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 1,2-diols. These are polyols containing an alcohol group at two adjacent positions.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Alcohols and polyols

Direct Parent

1,2-diols

Alternative Parents

Substituents

Cyclic ketone
Secondary alcohol
Ketone
1,2-diol
Organic oxide
Hydrocarbon derivative
Carbonyl group
Aldehyde
Aliphatic homomonocyclic compound

Molecular Framework

Aliphatic homomonocyclic 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	-0.13	ALOGPS
logP	0.022	ChemAxon
logS	-0.22	ALOGPS
pKa (Strongest Acidic)	12.31	ChemAxon
pKa (Strongest Basic)	-3.5	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	57.53 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	42.04 m³·mol⁻¹	ChemAxon
Polarizability	15.81 Å³	ChemAxon
Number of Rings	1	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

4941440

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Terrein

METLIN ID

Not Available

PubChem Compound

6436830

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Kahlert L, Bernardi D, Hauser M, Ioca LP, Berlinck RGS, Skellam EJ, Cox RJ: Early Oxidative Transformations During the Biosynthesis of Terrein and Related Natural Products. Chemistry. 2021 Jun 11. doi: 10.1002/chem.202101447. [PubMed:34114710 ]
Buachan P, Namsa-Aid M, Sung HK, Peng C, Sweeney G, Tanechpongtamb W: Inhibitory effects of terrein on lung cancer cell metastasis and angiogenesis. Oncol Rep. 2021 Jun;45(6). pii: 94. doi: 10.3892/or.2021.8045. Epub 2021 Apr 13. [PubMed:33846818 ]
Tilvi S, Parvatkar R, Singh KS, Devi P: Chemical Investigation of Marine-Derived Fungus Aspergillus flavipes for Potential Anti-Inflammatory Agents. Chem Biodivers. 2021 Feb;18(2):e2000956. doi: 10.1002/cbdv.202000956. Epub 2021 Feb 2. [PubMed:33533162 ]
Jiang YY, Yuan FL, Li JW, Wu HE, Wei MY, Shao CL, Liu M, Wang GH: Targeting Delivery Nanocarriers for (+)-Terrein to Enhance Its Anticancer Effects. ACS Omega. 2020 Oct 29;5(44):28889-28896. doi: 10.1021/acsomega.0c04571. eCollection 2020 Nov 10. [PubMed:33195942 ]
Liao, W. -Y., et al. (2012). Liao, W. -Y., et al, J. Nat. Prod. 75, 630 (2012). J. Nat. Prod..

Showing NP-Card for terrein (NP0036622)

MOL for NP0036622 (terrein)

3D MOL for NP0036622 (terrein)

3D SDF for NP0036622 (terrein)

3D-SDF for NP0036622 (terrein)

PDB for NP0036622 (terrein)

3D PDB for NP0036622 (terrein)

SMILES for NP0036622 (terrein)

INCHI for NP0036622 (terrein)

Structure for NP0036622 (terrein)

3D Structure for NP0036622 (terrein)