NP-MRD: Showing NP-Card for (5S,8R,9R,10S)-2S-Acetoxy-6S-hydroxyclerod-3,12,14-trien-18,19-dial (NP0333182)

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Record Information

Version

2.0

Created at

2024-05-12 05:29:50 UTC

Updated at

2024-09-03 04:21:30 UTC

NP-MRD ID

NP0333182

Natural Product DOI

https://doi.org/10.57994/2507

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(5S,8R,9R,10S)-2S-Acetoxy-6S-hydroxyclerod-3,12,14-trien-18,19-dial

Description

(5S,8R,9R,10S)-2S-Acetoxy-6S-hydroxyclerod-3,12,14-trien-18,19-dial belongs to the class of organic compounds known as colensane and clerodane diterpenoids. These are diterpenoids with a structure based on the clerodane or the colensane skeleton. Clerodanes arise from labdanes by two methyl migrations. (5S,8R,9R,10S)-2S-Acetoxy-6S-hydroxyclerod-3,12,14-trien-18,19-dial was first documented in 2022 (PMID: 35475609). Based on a literature review very few articles have been published on (5S,8R,9R,10S)-2S-Acetoxy-6S-hydroxyclerod-3,12,14-trien-18,19-dial .

Structure

MOL SDF PDB SMILES InChI


  Mrv2104 01242308062D          

 27 28  0  0  1  0            999 V2000
   -2.8579    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -0.4125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7145   -2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0000   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -0.0000    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.8986    0.6320    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9592    0.6320    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6771    1.4072    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2074    2.0392    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0198    1.8960    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9252    2.8145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1127    2.9577    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.8579   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.9139   -2.3174    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  2  4  1  0  0  0  0
  5  4  1  1  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
 10  7  1  0  0  0  0
 10 11  1  6  0  0  0
 11 12  2  0  0  0  0
 10 13  1  0  0  0  0
 13 14  1  1  0  0  0
  5 14  1  0  0  0  0
 13 15  1  0  0  0  0
 15 16  1  1  0  0  0
 15 17  1  6  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 19 20  1  0  0  0  0
 19 21  1  0  0  0  0
 21 22  2  0  0  0  0
 15 23  1  0  0  0  0
 23 24  1  6  0  0  0
 23 25  1  0  0  0  0
 26 25  1  0  0  0  0
 10 26  1  0  0  0  0
 26 27  1  6  0  0  0
M  END


  Mrv2104 01242308062D          

 27 28  0  0  1  0            999 V2000
   -2.8579    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -0.4125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7145   -2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0000   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -0.0000    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.8986    0.6320    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9592    0.6320    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6771    1.4072    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2074    2.0392    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0198    1.8960    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9252    2.8145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1127    2.9577    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.8579   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.9139   -2.3174    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  2  4  1  0  0  0  0
  5  4  1  1  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
 10  7  1  0  0  0  0
 10 11  1  6  0  0  0
 11 12  2  0  0  0  0
 10 13  1  0  0  0  0
 13 14  1  1  0  0  0
  5 14  1  0  0  0  0
 13 15  1  0  0  0  0
 15 16  1  1  0  0  0
 15 17  1  6  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 19 20  1  0  0  0  0
 19 21  1  0  0  0  0
 21 22  2  0  0  0  0
 15 23  1  0  0  0  0
 23 24  1  6  0  0  0
 23 25  1  0  0  0  0
 26 25  1  0  0  0  0
 10 26  1  0  0  0  0
 26 27  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0333182

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@@H]1C[C@H](O)[C@]2(C=O)[C@@H](C[C@H](OC(C)=O)C=C2C=O)[C@]1(C)C\C=C(/C)C=C

> <INCHI_IDENTIFIER>
InChI=1S/C22H30O5/c1-6-14(2)7-8-21(5)15(3)9-20(26)22(13-24)17(12-23)10-18(11-19(21)22)27-16(4)25/h6-7,10,12-13,15,18-20,26H,1,8-9,11H2,2-5H3/b14-7+/t15-,18-,19+,20+,21-,22+/m1/s1

> <INCHI_KEY>
RGJCQUBRIXHGCY-SEFCAVFISA-N

> <FORMULA>
C22H30O5

> <MOLECULAR_WEIGHT>
374.477

> <EXACT_MASS>
374.209324066

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
57

> <JCHEM_AVERAGE_POLARIZABILITY>
41.2751977531128

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2S,4aS,5S,7R,8R,8aS)-4,4a-diformyl-5-hydroxy-7,8-dimethyl-8-[(2E)-3-methylpenta-2,4-dien-1-yl]-1,2,4a,5,6,7,8,8a-octahydronaphthalen-2-yl acetate

> <JCHEM_LOGP>
2.1238159159999994

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.44545512983921

> <JCHEM_PKA_STRONGEST_BASIC>
-3.0413579262083292

> <JCHEM_POLAR_SURFACE_AREA>
80.67

> <JCHEM_REFRACTIVITY>
105.16179999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(2S,4aS,5S,7R,8R,8aS)-4,4a-diformyl-5-hydroxy-7,8-dimethyl-8-[(2E)-3-methylpenta-2,4-dien-1-yl]-1,2,5,6,7,8a-hexahydronaphthalen-2-yl acetate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 24-JAN-23   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-JAN-23         0                                  
HETATM    1  C   UNK     0      -5.335   0.000   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -4.001  -0.770   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0      -4.001  -2.310   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0      -2.667   0.000   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.000  -3.080   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.000  -4.620   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0      -1.334  -5.390   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.334  -3.850   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       2.667  -4.620   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       0.000  -0.000   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       2.667  -0.000   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       1.677   1.180   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       3.657   1.180   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       3.131   2.627   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       4.120   3.807   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       5.637   3.539   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       3.594   5.254   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       2.077   5.521   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       5.335  -0.000   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0       3.573  -4.326   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6   14                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8   10                                                  
CONECT    8    7    9                                                       
CONECT    9    8                                                            
CONECT   10    7   11   13   26                                             
CONECT   11   10   12                                                       
CONECT   12   11                                                            
CONECT   13   10   14   15                                                  
CONECT   14   13    5                                                       
CONECT   15   13   16   17   23                                             
CONECT   16   15                                                            
CONECT   17   15   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19   22                                                       
CONECT   22   21                                                            
CONECT   23   15   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23   26                                                       
CONECT   26   25   10   27                                                  
CONECT   27   26                                                            
MASTER        0    0    0    0    0    0    0    0   27    0   56    0
END

View in JSmol

Synonyms

Value	Source
(2S,4AR,5S,7R,8S,8as)-4,4a-diformyl-5-hydroxy-7,8-dimethyl-8-[(2E)-3-methylpenta-2,4-dien-1-yl]-2,4a,5,6,7,8a-hexahydro-1H-naphthalen-2-yl acetic acid	Generator

Chemical Formula

C₂₂H₃₀O₅

Average Mass

374.4770 Da

Monoisotopic Mass

374.20932 Da

IUPAC Name

(2S,4aS,5S,7R,8R,8aS)-4,4a-diformyl-5-hydroxy-7,8-dimethyl-8-[(2E)-3-methylpenta-2,4-dien-1-yl]-1,2,4a,5,6,7,8,8a-octahydronaphthalen-2-yl acetate

Traditional Name

(2S,4aS,5S,7R,8R,8aS)-4,4a-diformyl-5-hydroxy-7,8-dimethyl-8-[(2E)-3-methylpenta-2,4-dien-1-yl]-1,2,5,6,7,8a-hexahydronaphthalen-2-yl acetate

CAS Registry Number

Not Available

SMILES

C[C@@H]1C[C@H](O)[C@]2(C=O)[C@@H](C[C@H](OC(C)=O)C=C2C=O)[C@]1(C)C\C=C(/C)C=C

InChI Identifier

InChI=1S/C22H30O5/c1-6-14(2)7-8-21(5)15(3)9-20(26)22(13-24)17(12-23)10-18(11-19(21)22)27-16(4)25/h6-7,10,12-13,15,18-20,26H,1,8-9,11H2,2-5H3/b14-7+/t15-,18-,19+,20+,21-,22+/m1/s1

InChI Key

RGJCQUBRIXHGCY-SEFCAVFISA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
HSQC NMR	[¹H, ¹³C] NMR Spectrum (2D, 500 MHz, CDCl3, experimental)	eliane.garo@unibas.ch	Not Available	Not Available	2024-05-12	View Spectrum
COSY NMR	[¹H, ¹H] NMR Spectrum (2D, 500 MHz, CDCl3, experimental)	eliane.garo@unibas.ch	Not Available	Not Available	2024-05-12	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, CDCl3, experimental)	eliane.garo@unibas.ch	Not Available	Not Available	2024-05-12	View Spectrum
HMBC NMR	[¹H, ¹³C] NMR Spectrum (2D, 500 MHz, CDCl3, experimental)	eliane.garo@unibas.ch	Not Available	Not Available	2024-05-12	View Spectrum
NOESY NMR	[¹H, ¹H] NMR Spectrum (2D, 500 MHz, CDCl3, experimental)	eliane.garo@unibas.ch	Not Available	Not Available	2024-05-12	View Spectrum

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Casearia corymbosa		Not Available

Chemical Taxonomy

Description

This compound belongs to the class of organic compounds known as colensane and clerodane diterpenoids. These are diterpenoids with a structure based on the clerodane or the colensane skeleton. Clerodanes arise from labdanes by two methyl migrations.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Diterpenoids

Direct Parent

Colensane and clerodane diterpenoids

Alternative Parents

Substituents

Clerodane diterpenoid
Fatty alcohol ester
Beta-hydroxy aldehyde
Cyclic alcohol
Secondary alcohol
Carboxylic acid ester
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aldehyde
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	2.12	ChemAxon
pKa (Strongest Acidic)	14.45	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	80.67 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	105.16 m³·mol⁻¹	ChemAxon
Polarizability	41.28 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

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

168293772

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Syafni N, Faleschini MT, Garifulina A, Danton O, Gupta MP, Hering S, Hamburger M: Clerodane Diterpenes from Casearia corymbosa as Allosteric GABA(A) Receptor Modulators. J Nat Prod. 2022 May 27;85(5):1201-1210. doi: 10.1021/acs.jnatprod.1c00840. Epub 2022 Apr 27. [PubMed:35475609 ]
DOI: 10.1021/acs.jnatprod.1c00840

Showing NP-Card for (5S,8R,9R,10S)-2S-Acetoxy-6S-hydroxyclerod-3,12,14-trien-18,19-dial (NP0333182)

MOL for NP0333182 ((5S,8R,9R,10S)-2S-Acetoxy-6S-hydroxyclerod-3,12,14-trien-18,19-dial )

3D MOL for NP0333182 ((5S,8R,9R,10S)-2S-Acetoxy-6S-hydroxyclerod-3,12,14-trien-18,19-dial )

3D SDF for NP0333182 ((5S,8R,9R,10S)-2S-Acetoxy-6S-hydroxyclerod-3,12,14-trien-18,19-dial )

3D-SDF for NP0333182 ((5S,8R,9R,10S)-2S-Acetoxy-6S-hydroxyclerod-3,12,14-trien-18,19-dial )

PDB for NP0333182 ((5S,8R,9R,10S)-2S-Acetoxy-6S-hydroxyclerod-3,12,14-trien-18,19-dial )

3D PDB for NP0333182 ((5S,8R,9R,10S)-2S-Acetoxy-6S-hydroxyclerod-3,12,14-trien-18,19-dial )

SMILES for NP0333182 ((5S,8R,9R,10S)-2S-Acetoxy-6S-hydroxyclerod-3,12,14-trien-18,19-dial )

INCHI for NP0333182 ((5S,8R,9R,10S)-2S-Acetoxy-6S-hydroxyclerod-3,12,14-trien-18,19-dial )

Structure for NP0333182 ((5S,8R,9R,10S)-2S-Acetoxy-6S-hydroxyclerod-3,12,14-trien-18,19-dial )

3D Structure for NP0333182 ((5S,8R,9R,10S)-2S-Acetoxy-6S-hydroxyclerod-3,12,14-trien-18,19-dial )