NP-MRD: Showing NP-Card for Myrothec-15(17)-en-5,6,7,19-tetraol (NP0333515)

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Record Information

Version

2.0

Created at

2024-06-25 12:55:36 UTC

Updated at

2024-09-16 20:03:47 UTC

NP-MRD ID

NP0333515

Natural Product DOI

https://doi.org/10.57994/2969

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Myrothec-15(17)-en-5,6,7,19-tetraol

Description

Myrothec-15(17)-en-5,6,7,19-tetraol belongs to the class of organic compounds known as fusicoccane diterpenoids. These are diterpenoids with a structure based on a 20-carbon dicyclopenta[a,d]cyclooctane skeleton (5->8->5 ring system) known as fusicoccane. Based on a literature review very few articles have been published on Myrothec-15(17)-en-5,6,7,19-tetraol.

Structure

MOL SDF PDB SMILES InChI


  Mrv2104 03092315302D          

 26 28  0  0  1  0            999 V2000
    1.1157   -2.6732    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0509   -1.8507    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.3475   -1.4197    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5401   -0.6175    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0043    0.0099    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3625   -0.5527    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.8776    0.1147    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6783    0.2095    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.5706    1.0274    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2251    1.5296    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9336    0.5646    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4405    0.5252    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2027    0.2095    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5184   -0.5527    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.6934   -0.5527    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2027   -1.3149    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.8300   -1.8507    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5334   -1.4197    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3408   -0.6175    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.8766    0.0099    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6012    0.7875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6878   -0.1405    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0736   -2.1298    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4405   -1.6307    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6783   -1.3149    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.2616   -0.7316    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  1  0  0  0
  2  3  1  0  0  0  0
  4  3  1  0  0  0  0
  4  5  1  6  0  0  0
  6  4  1  0  0  0  0
  6  7  1  6  0  0  0
  6  8  1  0  0  0  0
  8  9  1  1  0  0  0
  9 10  1  0  0  0  0
  8 11  1  6  0  0  0
  8 12  1  0  0  0  0
 12 13  1  0  0  0  0
 14 13  1  0  0  0  0
 14 15  1  6  0  0  0
 14 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 19 18  1  0  0  0  0
 14 19  1  0  0  0  0
 19 20  1  6  0  0  0
 20 21  1  0  0  0  0
 20 22  2  0  0  0  0
 16 23  1  1  0  0  0
 16 24  1  0  0  0  0
 25 24  1  0  0  0  0
  6 25  1  0  0  0  0
 25  2  1  0  0  0  0
 25 26  1  6  0  0  0
M  END


  Mrv2104 03092315302D          

 26 28  0  0  1  0            999 V2000
    1.1157   -2.6732    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0509   -1.8507    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.3475   -1.4197    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5401   -0.6175    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0043    0.0099    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3625   -0.5527    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.8776    0.1147    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6783    0.2095    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.5706    1.0274    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2251    1.5296    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9336    0.5646    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4405    0.5252    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2027    0.2095    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5184   -0.5527    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.6934   -0.5527    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2027   -1.3149    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.8300   -1.8507    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5334   -1.4197    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3408   -0.6175    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.8766    0.0099    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6012    0.7875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6878   -0.1405    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0736   -2.1298    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4405   -1.6307    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6783   -1.3149    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.2616   -0.7316    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  1  0  0  0
  2  3  1  0  0  0  0
  4  3  1  0  0  0  0
  4  5  1  6  0  0  0
  6  4  1  0  0  0  0
  6  7  1  6  0  0  0
  6  8  1  0  0  0  0
  8  9  1  1  0  0  0
  9 10  1  0  0  0  0
  8 11  1  6  0  0  0
  8 12  1  0  0  0  0
 12 13  1  0  0  0  0
 14 13  1  0  0  0  0
 14 15  1  6  0  0  0
 14 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 19 18  1  0  0  0  0
 14 19  1  0  0  0  0
 19 20  1  6  0  0  0
 20 21  1  0  0  0  0
 20 22  2  0  0  0  0
 16 23  1  1  0  0  0
 16 24  1  0  0  0  0
 25 24  1  0  0  0  0
  6 25  1  0  0  0  0
 25  2  1  0  0  0  0
 25 26  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0333515

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H][C@@]12CC[C@](O)(CO)[C@]3(O)[C@@H](O)C[C@H](C)[C@]3([H])C[C@@]1(C)CC[C@H]2C(C)=C

> <INCHI_IDENTIFIER>
InChI=1S/C20H34O4/c1-12(2)14-5-7-18(4)10-16-13(3)9-17(22)20(16,24)19(23,11-21)8-6-15(14)18/h13-17,21-24H,1,5-11H2,2-4H3/t13-,14-,15-,16-,17-,18+,19-,20+/m0/s1

> <INCHI_KEY>
YOVCQFKRQWOIAM-KKVRMWHZSA-N

> <FORMULA>
C20H34O4

> <MOLECULAR_WEIGHT>
338.488

> <EXACT_MASS>
338.245709575

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
58

> <JCHEM_AVERAGE_POLARIZABILITY>
38.67395274026232

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1R,3S,4S,6S,7R,8S,11S,12R)-8-(hydroxymethyl)-1,4-dimethyl-12-(prop-1-en-2-yl)tricyclo[9.3.0.0^{3,7}]tetradecane-6,7,8-triol

> <JCHEM_LOGP>
1.7709444856666674

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.63345250409405

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.375124381482058

> <JCHEM_PKA_STRONGEST_BASIC>
-3.1128777226929745

> <JCHEM_POLAR_SURFACE_AREA>
80.92

> <JCHEM_REFRACTIVITY>
93.6094

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(1R,3S,4S,6S,7R,8S,11S,12R)-8-(hydroxymethyl)-1,4-dimethyl-12-(prop-1-en-2-yl)tricyclo[9.3.0.0^{3,7}]tetradecane-6,7,8-triol

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 09-MAR-23   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   09-MAR-23         0                                  
HETATM    1  C   UNK     0       2.083  -4.990   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.962  -3.455   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.649  -2.650   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.008  -1.153   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0       0.008   0.018   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       2.543  -1.032   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       1.638   0.214   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       3.133   0.391   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.932   1.918   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       4.154   2.855   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0       1.743   1.054   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       4.556   0.980   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       5.978   0.391   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       6.568  -1.032   0.000  0.00  0.00           C+0
HETATM   15  H   UNK     0       5.028  -1.032   0.000  0.00  0.00           H+0
HETATM   16  C   UNK     0       5.978  -2.455   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       7.149  -3.455   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       8.462  -2.650   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       8.103  -1.153   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       9.103   0.018   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       8.589   1.470   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      10.617  -0.262   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       5.737  -3.976   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       4.556  -3.044   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       3.133  -2.455   0.000  0.00  0.00           C+0
HETATM   26  H   UNK     0       4.222  -1.366   0.000  0.00  0.00           H+0
CONECT    1    2                                                            
CONECT    2    1    3   25                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7    8   25                                             
CONECT    7    6                                                            
CONECT    8    6    9   11   12                                             
CONECT    9    8   10                                                       
CONECT   10    9                                                            
CONECT   11    8                                                            
CONECT   12    8   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15   16   19                                             
CONECT   15   14                                                            
CONECT   16   14   17   23   24                                             
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   14   20                                                  
CONECT   20   19   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20                                                            
CONECT   23   16                                                            
CONECT   24   16   25                                                       
CONECT   25   24    6    2   26                                             
CONECT   26   25                                                            
MASTER        0    0    0    0    0    0    0    0   26    0   56    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₀H₃₄O₄

Average Mass

338.4880 Da

Monoisotopic Mass

338.24571 Da

IUPAC Name

(1R,3S,4S,6S,7R,8S,11S,12R)-8-(hydroxymethyl)-1,4-dimethyl-12-(prop-1-en-2-yl)tricyclo[9.3.0.0^{3,7}]tetradecane-6,7,8-triol

Traditional Name

(1R,3S,4S,6S,7R,8S,11S,12R)-8-(hydroxymethyl)-1,4-dimethyl-12-(prop-1-en-2-yl)tricyclo[9.3.0.0^{3,7}]tetradecane-6,7,8-triol

CAS Registry Number

Not Available

SMILES

[H][C@@]12CC[C@](O)(CO)[C@]3(O)[C@@H](O)C[C@H](C)[C@]3([H])C[C@@]1(C)CC[C@H]2C(C)=C

InChI Identifier

InChI=1S/C20H34O4/c1-12(2)14-5-7-18(4)10-16-13(3)9-17(22)20(16,24)19(23,11-21)8-6-15(14)18/h13-17,21-24H,1,5-11H2,2-4H3/t13-,14-,15-,16-,17-,18+,19-,20+/m0/s1

InChI Key

YOVCQFKRQWOIAM-KKVRMWHZSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, CD3OD, experimental)	838071903@qq.com	jinan university	FuLong Lin	2024-06-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, CD3OD, experimental)	838071903@qq.com	jinan university	FuLong Lin	2024-06-25	View Spectrum

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View

Chemical Shift Submissions

Not Available

Species

Species of Origin

Not Available

Chemical Taxonomy

Description

This compound belongs to the class of organic compounds known as fusicoccane diterpenoids. These are diterpenoids with a structure based on a 20-carbon dicyclopenta[a,d]cyclooctane skeleton (5->8->5 ring system) known as fusicoccane.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Diterpenoids

Direct Parent

Fusicoccane diterpenoids

Alternative Parents

Substituents

Fusicoccane diterpenoid
Long chain fatty alcohol
Fatty alcohol
Fatty acyl
Tertiary alcohol
Cyclic alcohol
Secondary alcohol
Organic oxygen compound
Hydrocarbon derivative
Organooxygen compound
Alcohol
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic 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	1.77	ChemAxon
pKa (Strongest Acidic)	12.38	ChemAxon
pKa (Strongest Basic)	-3.1	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	80.92 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	93.61 m³·mol⁻¹	ChemAxon
Polarizability	38.67 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	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

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Myrothec-15(17)-en-5,6,7,19-tetraol (NP0333515)

MOL for NP0333515 (Myrothec-15(17)-en-5,6,7,19-tetraol)

3D MOL for NP0333515 (Myrothec-15(17)-en-5,6,7,19-tetraol)

3D SDF for NP0333515 (Myrothec-15(17)-en-5,6,7,19-tetraol)

3D-SDF for NP0333515 (Myrothec-15(17)-en-5,6,7,19-tetraol)

PDB for NP0333515 (Myrothec-15(17)-en-5,6,7,19-tetraol)

3D PDB for NP0333515 (Myrothec-15(17)-en-5,6,7,19-tetraol)

SMILES for NP0333515 (Myrothec-15(17)-en-5,6,7,19-tetraol)

INCHI for NP0333515 (Myrothec-15(17)-en-5,6,7,19-tetraol)

Structure for NP0333515 (Myrothec-15(17)-en-5,6,7,19-tetraol)

3D Structure for NP0333515 (Myrothec-15(17)-en-5,6,7,19-tetraol)