NP-MRD: Showing NP-Card for (3ar,6as,7s,8r,10s,10ar,10bs)-3a,7,8,10a-tetrahydroxy-5-(hydroxymethyl)-2,10-dimethyl-8-(prop-1-en-2-yl)-4h,6ah,7h,9h,10h,10bh-cyclohexa[e]azulen-3-one (NP0304418)

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Record Information

Version

2.0

Created at

2022-09-10 19:29:47 UTC

Updated at

2022-09-10 19:29:47 UTC

NP-MRD ID

NP0304418

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(3ar,6as,7s,8r,10s,10ar,10bs)-3a,7,8,10a-tetrahydroxy-5-(hydroxymethyl)-2,10-dimethyl-8-(prop-1-en-2-yl)-4h,6ah,7h,9h,10h,10bh-cyclohexa[e]azulen-3-one

Description

(3AR,6aS,7S,8R,10S,10aR,10bS)-3a,7,8,10a-tetrahydroxy-5-(hydroxymethyl)-2,10-dimethyl-8-(prop-1-en-2-yl)-3H,3aH,4H,6aH,7H,8H,9H,10H,10aH,10bH-cyclohexa[e]azulen-3-one belongs to the class of organic compounds known as rhamnofolane and daphnane diterpenoids. These are diterpenoids with a structure based on one the rhamnofolane or daphnane skeleton. The rhamnofolane and daphnane skeletons are closely related, being formally derived from casbane by two cyclizations (6,10 and 5,14) followed by cleavage of the 1,15 (daphnane) or 2,15 (rhamnofolane) cyclopropane bonds. (3ar,6as,7s,8r,10s,10ar,10bs)-3a,7,8,10a-tetrahydroxy-5-(hydroxymethyl)-2,10-dimethyl-8-(prop-1-en-2-yl)-4h,6ah,7h,9h,10h,10bh-cyclohexa[e]azulen-3-one is found in Euphorbia resinifera. Based on a literature review very few articles have been published on (3aR,6aS,7S,8R,10S,10aR,10bS)-3a,7,8,10a-tetrahydroxy-5-(hydroxymethyl)-2,10-dimethyl-8-(prop-1-en-2-yl)-3H,3aH,4H,6aH,7H,8H,9H,10H,10aH,10bH-cyclohexa[e]azulen-3-one.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652309102221292D          

 26 28  0  0  1  0            999 V2000
    5.6410    1.2740    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8731    0.4823    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6747    0.2874    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3034   -0.1145    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.9901   -0.5718    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8146    0.5501    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9947    0.4591    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.5059    1.1237    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6635   -0.2965    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.2257    0.4028    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1523   -0.9611    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.9375   -1.7576    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1808   -2.0863    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1486   -2.9107    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4186   -3.2950    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4520   -1.6996    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3000   -0.8888    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.6580   -1.4069    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5395   -0.5689    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8338   -0.9962    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6087    0.2531    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9842    0.7923    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4119    0.4414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8392   -0.2643    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.9723   -0.8701    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.4611   -1.5347    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  4  2  1  1  0  0  0
  4  5  1  6  0  0  0
  4  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  1  0  0  0
  7  9  1  0  0  0  0
  9 10  1  6  0  0  0
  9 11  1  0  0  0  0
 11 12  1  6  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 13 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  1  0  0  0
 17 19  1  0  0  0  0
 19 20  2  0  0  0  0
 19 21  1  0  0  0  0
 21 22  1  0  0  0  0
 21 23  2  0  0  0  0
 24 23  1  1  0  0  0
 17 24  1  0  0  0  0
  9 24  1  0  0  0  0
 11 25  1  0  0  0  0
  4 25  1  0  0  0  0
 25 26  1  1  0  0  0
M  END


  Mrv1652309102221292D          

 26 28  0  0  1  0            999 V2000
    5.6410    1.2740    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8731    0.4823    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6747    0.2874    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3034   -0.1145    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.9901   -0.5718    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8146    0.5501    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9947    0.4591    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.5059    1.1237    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6635   -0.2965    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.2257    0.4028    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1523   -0.9611    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.9375   -1.7576    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1808   -2.0863    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1486   -2.9107    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4186   -3.2950    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4520   -1.6996    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3000   -0.8888    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.6580   -1.4069    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5395   -0.5689    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8338   -0.9962    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6087    0.2531    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9842    0.7923    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4119    0.4414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8392   -0.2643    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.9723   -0.8701    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.4611   -1.5347    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  4  2  1  1  0  0  0
  4  5  1  6  0  0  0
  4  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  1  0  0  0
  7  9  1  0  0  0  0
  9 10  1  6  0  0  0
  9 11  1  0  0  0  0
 11 12  1  6  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 13 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  1  0  0  0
 17 19  1  0  0  0  0
 19 20  2  0  0  0  0
 19 21  1  0  0  0  0
 21 22  1  0  0  0  0
 21 23  2  0  0  0  0
 24 23  1  1  0  0  0
 17 24  1  0  0  0  0
  9 24  1  0  0  0  0
 11 25  1  0  0  0  0
  4 25  1  0  0  0  0
 25 26  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0304418

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@H]1C[C@](O)([C@@H](O)[C@@H]2C=C(CO)C[C@@]3(O)[C@@H](C=C(C)C3=O)[C@@]12O)C(C)=C

> <INCHI_IDENTIFIER>
InChI=1S/C20H28O6/c1-10(2)18(24)7-12(4)20(26)14(17(18)23)6-13(9-21)8-19(25)15(20)5-11(3)16(19)22/h5-6,12,14-15,17,21,23-26H,1,7-9H2,2-4H3/t12-,14-,15+,17-,18+,19+,20+/m0/s1

> <INCHI_KEY>
XJOIANWCBZYENR-DBCWNCDWSA-N

> <FORMULA>
C20H28O6

> <MOLECULAR_WEIGHT>
364.438

> <EXACT_MASS>
364.188588622

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
54

> <JCHEM_AVERAGE_POLARIZABILITY>
38.398418656385424

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(3aR,6aS,7S,8R,10S,10aR,10bS)-3a,7,8,10a-tetrahydroxy-5-(hydroxymethyl)-2,10-dimethyl-8-(prop-1-en-2-yl)-3H,3aH,4H,6aH,7H,8H,9H,10H,10aH,10bH-cyclohexa[e]azulen-3-one

> <JCHEM_LOGP>
-0.4406852689999987

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.154011673932455

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.459181790278958

> <JCHEM_PKA_STRONGEST_BASIC>
-2.7319993017817037

> <JCHEM_POLAR_SURFACE_AREA>
118.22000000000001

> <JCHEM_REFRACTIVITY>
97.6124

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(3aR,6aS,7S,8R,10S,10aR,10bS)-3a,7,8,10a-tetrahydroxy-5-(hydroxymethyl)-2,10-dimethyl-8-(prop-1-en-2-yl)-4H,6aH,7H,9H,10H,10bH-cyclohexa[e]azulen-3-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 10-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   10-SEP-22         0                                  
HETATM    1  C   UNK     0      10.530   2.378   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      10.963   0.900   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      12.459   0.537   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       9.900  -0.214   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0      11.181  -1.067   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       8.987   1.027   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       7.457   0.857   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       6.544   2.098   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       6.839  -0.553   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       6.021   0.752   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       7.751  -1.794   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       7.350  -3.281   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       5.937  -3.894   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       5.877  -5.433   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       4.515  -6.151   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       4.577  -3.173   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       4.293  -1.659   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       3.095  -2.626   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       2.874  -1.062   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       1.556  -1.860   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       3.003   0.473   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       1.837   1.479   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       4.502   0.824   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       5.300  -0.493   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       9.282  -1.624   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0      10.194  -2.865   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5    6   25                                             
CONECT    5    4                                                            
CONECT    6    4    7                                                       
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10   11   24                                             
CONECT   10    9                                                            
CONECT   11    9   12   25                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14   16                                                  
CONECT   14   13   15                                                       
CONECT   15   14                                                            
CONECT   16   13   17                                                       
CONECT   17   16   18   19   24                                             
CONECT   18   17                                                            
CONECT   19   17   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21   24                                                       
CONECT   24   23   17    9                                                  
CONECT   25   11    4   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

C₂₀H₂₈O₆

Average Mass

364.4380 Da

Monoisotopic Mass

364.18859 Da

IUPAC Name

(3aR,6aS,7S,8R,10S,10aR,10bS)-3a,7,8,10a-tetrahydroxy-5-(hydroxymethyl)-2,10-dimethyl-8-(prop-1-en-2-yl)-3H,3aH,4H,6aH,7H,8H,9H,10H,10aH,10bH-cyclohexa[e]azulen-3-one

Traditional Name

(3aR,6aS,7S,8R,10S,10aR,10bS)-3a,7,8,10a-tetrahydroxy-5-(hydroxymethyl)-2,10-dimethyl-8-(prop-1-en-2-yl)-4H,6aH,7H,9H,10H,10bH-cyclohexa[e]azulen-3-one

CAS Registry Number

Not Available

SMILES

C[C@H]1C[C@](O)([C@@H](O)[C@@H]2C=C(CO)C[C@@]3(O)[C@@H](C=C(C)C3=O)[C@@]12O)C(C)=C

InChI Identifier

InChI=1S/C20H28O6/c1-10(2)18(24)7-12(4)20(26)14(17(18)23)6-13(9-21)8-19(25)15(20)5-11(3)16(19)22/h5-6,12,14-15,17,21,23-26H,1,7-9H2,2-4H3/t12-,14-,15+,17-,18+,19+,20+/m0/s1

InChI Key

XJOIANWCBZYENR-DBCWNCDWSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Euphorbia resinifera	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as rhamnofolane and daphnane diterpenoids. These are diterpenoids with a structure based on one the rhamnofolane or daphnane skeleton. The rhamnofolane and daphnane skeletons are closely related, being formally derived from casbane by two cyclizations (6,10 and 5,14) followed by cleavage of the 1,15 (daphnane) or 2,15 (rhamnofolane) cyclopropane bonds.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Diterpenoids

Direct Parent

Rhamnofolane and daphnane diterpenoids

Alternative Parents

Substituents

Daphnane diterpenoid
Tertiary alcohol
Cyclic alcohol
Secondary alcohol
Ketone
Polyol
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Primary alcohol
Organooxygen compound
Carbonyl group
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	-0.44	ChemAxon
pKa (Strongest Acidic)	12.46	ChemAxon
pKa (Strongest Basic)	-2.7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	118.22 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	97.61 m³·mol⁻¹	ChemAxon
Polarizability	38.4 Å³	ChemAxon
Number of Rings	3	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

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

162995428

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (3ar,6as,7s,8r,10s,10ar,10bs)-3a,7,8,10a-tetrahydroxy-5-(hydroxymethyl)-2,10-dimethyl-8-(prop-1-en-2-yl)-4h,6ah,7h,9h,10h,10bh-cyclohexa[e]azulen-3-one (NP0304418)

MOL for NP0304418 ((3ar,6as,7s,8r,10s,10ar,10bs)-3a,7,8,10a-tetrahydroxy-5-(hydroxymethyl)-2,10-dimethyl-8-(prop-1-en-2-yl)-4h,6ah,7h,9h,10h,10bh-cyclohexa[e]azulen-3-one)

3D MOL for NP0304418 ((3ar,6as,7s,8r,10s,10ar,10bs)-3a,7,8,10a-tetrahydroxy-5-(hydroxymethyl)-2,10-dimethyl-8-(prop-1-en-2-yl)-4h,6ah,7h,9h,10h,10bh-cyclohexa[e]azulen-3-one)

3D SDF for NP0304418 ((3ar,6as,7s,8r,10s,10ar,10bs)-3a,7,8,10a-tetrahydroxy-5-(hydroxymethyl)-2,10-dimethyl-8-(prop-1-en-2-yl)-4h,6ah,7h,9h,10h,10bh-cyclohexa[e]azulen-3-one)

3D-SDF for NP0304418 ((3ar,6as,7s,8r,10s,10ar,10bs)-3a,7,8,10a-tetrahydroxy-5-(hydroxymethyl)-2,10-dimethyl-8-(prop-1-en-2-yl)-4h,6ah,7h,9h,10h,10bh-cyclohexa[e]azulen-3-one)

PDB for NP0304418 ((3ar,6as,7s,8r,10s,10ar,10bs)-3a,7,8,10a-tetrahydroxy-5-(hydroxymethyl)-2,10-dimethyl-8-(prop-1-en-2-yl)-4h,6ah,7h,9h,10h,10bh-cyclohexa[e]azulen-3-one)

3D PDB for NP0304418 ((3ar,6as,7s,8r,10s,10ar,10bs)-3a,7,8,10a-tetrahydroxy-5-(hydroxymethyl)-2,10-dimethyl-8-(prop-1-en-2-yl)-4h,6ah,7h,9h,10h,10bh-cyclohexa[e]azulen-3-one)

SMILES for NP0304418 ((3ar,6as,7s,8r,10s,10ar,10bs)-3a,7,8,10a-tetrahydroxy-5-(hydroxymethyl)-2,10-dimethyl-8-(prop-1-en-2-yl)-4h,6ah,7h,9h,10h,10bh-cyclohexa[e]azulen-3-one)

INCHI for NP0304418 ((3ar,6as,7s,8r,10s,10ar,10bs)-3a,7,8,10a-tetrahydroxy-5-(hydroxymethyl)-2,10-dimethyl-8-(prop-1-en-2-yl)-4h,6ah,7h,9h,10h,10bh-cyclohexa[e]azulen-3-one)

Structure for NP0304418 ((3ar,6as,7s,8r,10s,10ar,10bs)-3a,7,8,10a-tetrahydroxy-5-(hydroxymethyl)-2,10-dimethyl-8-(prop-1-en-2-yl)-4h,6ah,7h,9h,10h,10bh-cyclohexa[e]azulen-3-one)

3D Structure for NP0304418 ((3ar,6as,7s,8r,10s,10ar,10bs)-3a,7,8,10a-tetrahydroxy-5-(hydroxymethyl)-2,10-dimethyl-8-(prop-1-en-2-yl)-4h,6ah,7h,9h,10h,10bh-cyclohexa[e]azulen-3-one)