NP-MRD: Showing NP-Card for 5-(1-hydroxypropan-2-yl)-6,9-dimethyl-15-oxatetracyclo[7.6.1.0²,⁶.0¹³,¹⁶]hexadec-13(16)-ene-3,4,12-triol (NP0193072)

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Record Information

Version

2.0

Created at

2022-09-04 10:25:28 UTC

Updated at

2022-09-04 10:25:29 UTC

NP-MRD ID

NP0193072

Secondary Accession Numbers

None

Natural Product Identification

Common Name

5-(1-hydroxypropan-2-yl)-6,9-dimethyl-15-oxatetracyclo[7.6.1.0²,⁶.0¹³,¹⁶]hexadec-13(16)-ene-3,4,12-triol

Description

5-(1-Hydroxypropan-2-yl)-6,9-dimethyl-15-oxatetracyclo[7.6.1.0²,⁶.0¹³,¹⁶]Hexadec-13(16)-ene-3,4,12-triol belongs to the class of organic compounds known as dihydrofurans. Dihydrofurans are compounds containing a dihydrofuran moiety, which is a furan derivative with only one double bond. 5-(1-hydroxypropan-2-yl)-6,9-dimethyl-15-oxatetracyclo[7.6.1.0²,⁶.0¹³,¹⁶]hexadec-13(16)-ene-3,4,12-triol is found in Verticillium dahliae. Based on a literature review very few articles have been published on 5-(1-hydroxypropan-2-yl)-6,9-dimethyl-15-oxatetracyclo[7.6.1.0²,⁶.0¹³,¹⁶]Hexadec-13(16)-ene-3,4,12-triol.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652309042212252D          

 25 28  0  0  0  0            999 V2000
    4.9676    3.1783    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3500    2.4473    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1743    2.4129    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6162    3.1096    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9081    1.7506    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2120    0.9836    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0111    0.7786    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5764    0.4576    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6284   -0.3658    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8797    0.8995    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1271    0.5615    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9946   -0.2528    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1792   -0.3784    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8078    0.3583    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3937    0.9392    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2316    1.7481    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9754    2.5323    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3876    1.9539    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8017    1.3730    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0119    0.5752    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4260   -0.0056    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7631    2.3792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5878    2.3571    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0847    1.6986    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4291    2.4483    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  2  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  6  8  1  0  0  0  0
  8  9  1  0  0  0  0
  8 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 11 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 16 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 14 20  1  0  0  0  0
 20 21  1  0  0  0  0
 16 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
  5 24  1  0  0  0  0
 10 24  1  0  0  0  0
 24 25  1  0  0  0  0
M  END


  Mrv1652309042212252D          

 25 28  0  0  0  0            999 V2000
    4.9676    3.1783    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3500    2.4473    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1743    2.4129    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6162    3.1096    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9081    1.7506    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2120    0.9836    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0111    0.7786    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5764    0.4576    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6284   -0.3658    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8797    0.8995    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1271    0.5615    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9946   -0.2528    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1792   -0.3784    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8078    0.3583    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3937    0.9392    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2316    1.7481    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9754    2.5323    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3876    1.9539    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8017    1.3730    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0119    0.5752    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4260   -0.0056    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7631    2.3792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5878    2.3571    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0847    1.6986    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4291    2.4483    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  2  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  6  8  1  0  0  0  0
  8  9  1  0  0  0  0
  8 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 11 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 16 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 14 20  1  0  0  0  0
 20 21  1  0  0  0  0
 16 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
  5 24  1  0  0  0  0
 10 24  1  0  0  0  0
 24 25  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0193072

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(CO)C1C(O)C(O)C2C3OCC4=C3C(C)(CCC4O)CCC12C

> <INCHI_IDENTIFIER>
InChI=1S/C20H32O5/c1-10(8-21)13-16(23)17(24)15-18-14-11(9-25-18)12(22)4-5-19(14,2)6-7-20(13,15)3/h10,12-13,15-18,21-24H,4-9H2,1-3H3

> <INCHI_KEY>
GSCMNDGHAGKYNL-UHFFFAOYSA-N

> <FORMULA>
C20H32O5

> <MOLECULAR_WEIGHT>
352.471

> <EXACT_MASS>
352.22497413

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
57

> <JCHEM_AVERAGE_POLARIZABILITY>
39.48811789905298

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
5-(1-hydroxypropan-2-yl)-6,9-dimethyl-15-oxatetracyclo[7.6.1.0^{2,6}.0^{13,16}]hexadec-13(16)-ene-3,4,12-triol

> <JCHEM_LOGP>
-0.08077843399999948

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.413920703758645

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.527973805042286

> <JCHEM_PKA_STRONGEST_BASIC>
-2.5949726506630197

> <JCHEM_POLAR_SURFACE_AREA>
90.15

> <JCHEM_REFRACTIVITY>
94.3059

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
5-(1-hydroxypropan-2-yl)-6,9-dimethyl-15-oxatetracyclo[7.6.1.0^{2,6}.0^{13,16}]hexadec-13(16)-ene-3,4,12-triol

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 04-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   04-SEP-22         0                                  
HETATM    1  C   UNK     0       9.273   5.933   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       9.987   4.568   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      11.525   4.504   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0      12.350   5.805   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       9.162   3.268   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       9.729   1.836   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      11.221   1.453   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       8.543   0.854   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       8.640  -0.683   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       7.242   1.679   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.837   1.048   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       5.590  -0.472   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       4.068  -0.706   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       3.375   0.669   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.468   1.753   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       4.166   3.263   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       3.687   4.727   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       2.590   3.647   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       1.497   2.563   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       1.889   1.074   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       0.795  -0.010   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       5.158   4.441   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       6.697   4.400   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       7.625   3.171   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       8.268   4.570   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    5                                                  
CONECT    3    2    4                                                       
CONECT    4    3                                                            
CONECT    5    2    6   24                                                  
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11   24                                                  
CONECT   11   10   12   15                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15   20                                                  
CONECT   15   14   11   16                                                  
CONECT   16   15   17   18   22                                             
CONECT   17   16                                                            
CONECT   18   16   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   14   21                                                  
CONECT   21   20                                                            
CONECT   22   16   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23    5   10   25                                             
CONECT   25   24                                                            
MASTER        0    0    0    0    0    0    0    0   25    0   56    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₀H₃₂O₅

Average Mass

352.4710 Da

Monoisotopic Mass

352.22497 Da

IUPAC Name

5-(1-hydroxypropan-2-yl)-6,9-dimethyl-15-oxatetracyclo[7.6.1.0^{2,6}.0^{13,16}]hexadec-13(16)-ene-3,4,12-triol

Traditional Name

5-(1-hydroxypropan-2-yl)-6,9-dimethyl-15-oxatetracyclo[7.6.1.0^{2,6}.0^{13,16}]hexadec-13(16)-ene-3,4,12-triol

CAS Registry Number

Not Available

SMILES

CC(CO)C1C(O)C(O)C2C3OCC4=C3C(C)(CCC4O)CCC12C

InChI Identifier

InChI=1S/C20H32O5/c1-10(8-21)13-16(23)17(24)15-18-14-11(9-25-18)12(22)4-5-19(14,2)6-7-20(13,15)3/h10,12-13,15-18,21-24H,4-9H2,1-3H3

InChI Key

GSCMNDGHAGKYNL-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Verticillium dahliae	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as dihydrofurans. Dihydrofurans are compounds containing a dihydrofuran moiety, which is a furan derivative with only one double bond.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Dihydrofurans

Sub Class

Not Available

Direct Parent

Dihydrofurans

Alternative Parents

Substituents

Dihydrofuran
Cyclic alcohol
Secondary alcohol
Oxacycle
Polyol
Ether
Dialkyl ether
Organic oxygen compound
Hydrocarbon derivative
Primary alcohol
Organooxygen compound
Alcohol
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic 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	-0.081	ChemAxon
pKa (Strongest Acidic)	13.53	ChemAxon
pKa (Strongest Basic)	-2.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	90.15 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	94.31 m³·mol⁻¹	ChemAxon
Polarizability	39.49 Å³	ChemAxon
Number of Rings	4	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

162814800

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 5-(1-hydroxypropan-2-yl)-6,9-dimethyl-15-oxatetracyclo[7.6.1.0²,⁶.0¹³,¹⁶]hexadec-13(16)-ene-3,4,12-triol (NP0193072)

MOL for NP0193072 (5-(1-hydroxypropan-2-yl)-6,9-dimethyl-15-oxatetracyclo[7.6.1.0²,⁶.0¹³,¹⁶]hexadec-13(16)-ene-3,4,12-triol)

3D MOL for NP0193072 (5-(1-hydroxypropan-2-yl)-6,9-dimethyl-15-oxatetracyclo[7.6.1.0²,⁶.0¹³,¹⁶]hexadec-13(16)-ene-3,4,12-triol)

3D SDF for NP0193072 (5-(1-hydroxypropan-2-yl)-6,9-dimethyl-15-oxatetracyclo[7.6.1.0²,⁶.0¹³,¹⁶]hexadec-13(16)-ene-3,4,12-triol)

3D-SDF for NP0193072 (5-(1-hydroxypropan-2-yl)-6,9-dimethyl-15-oxatetracyclo[7.6.1.0²,⁶.0¹³,¹⁶]hexadec-13(16)-ene-3,4,12-triol)

PDB for NP0193072 (5-(1-hydroxypropan-2-yl)-6,9-dimethyl-15-oxatetracyclo[7.6.1.0²,⁶.0¹³,¹⁶]hexadec-13(16)-ene-3,4,12-triol)

3D PDB for NP0193072 (5-(1-hydroxypropan-2-yl)-6,9-dimethyl-15-oxatetracyclo[7.6.1.0²,⁶.0¹³,¹⁶]hexadec-13(16)-ene-3,4,12-triol)

SMILES for NP0193072 (5-(1-hydroxypropan-2-yl)-6,9-dimethyl-15-oxatetracyclo[7.6.1.0²,⁶.0¹³,¹⁶]hexadec-13(16)-ene-3,4,12-triol)

INCHI for NP0193072 (5-(1-hydroxypropan-2-yl)-6,9-dimethyl-15-oxatetracyclo[7.6.1.0²,⁶.0¹³,¹⁶]hexadec-13(16)-ene-3,4,12-triol)

Structure for NP0193072 (5-(1-hydroxypropan-2-yl)-6,9-dimethyl-15-oxatetracyclo[7.6.1.0²,⁶.0¹³,¹⁶]hexadec-13(16)-ene-3,4,12-triol)

3D Structure for NP0193072 (5-(1-hydroxypropan-2-yl)-6,9-dimethyl-15-oxatetracyclo[7.6.1.0²,⁶.0¹³,¹⁶]hexadec-13(16)-ene-3,4,12-triol)