NP-MRD: Showing NP-Card for 1,4a-dihydroxy-1-isopropyl-3a,8a-dimethyl-5-methylidene-2h,3h,4h,6h,7h,8h,9h-cyclohexa[f]azulen-8-yl acetate (NP0273933)

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Record Information

Version

2.0

Created at

2022-09-08 21:08:20 UTC

Updated at

2022-09-08 21:08:20 UTC

NP-MRD ID

NP0273933

Secondary Accession Numbers

None

Natural Product Identification

Common Name

1,4a-dihydroxy-1-isopropyl-3a,8a-dimethyl-5-methylidene-2h,3h,4h,6h,7h,8h,9h-cyclohexa[f]azulen-8-yl acetate

Description

1,4A-dihydroxy-3a,8a-dimethyl-5-methylidene-1-(propan-2-yl)-1H,2H,3H,3aH,4H,4aH,5H,6H,7H,8H,8aH,9H-cyclohexa[f]azulen-8-yl acetate belongs to the class of organic compounds known as diterpenoids. These are terpene compounds formed by four isoprene units. 1,4a-dihydroxy-1-isopropyl-3a,8a-dimethyl-5-methylidene-2h,3h,4h,6h,7h,8h,9h-cyclohexa[f]azulen-8-yl acetate is found in Canistrocarpus cervicornis and Dictyota divaricata. 1,4A-dihydroxy-3a,8a-dimethyl-5-methylidene-1-(propan-2-yl)-1H,2H,3H,3aH,4H,4aH,5H,6H,7H,8H,8aH,9H-cyclohexa[f]azulen-8-yl acetate is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL SDF PDB SMILES InChI


  Mrv1533004181502232D          

 26 28  0  0  0  0            999 V2000
   -0.5826   -1.2410    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0158   -1.8088    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1767   -2.6111    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8068   -1.5745    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9572   -2.3857    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4911   -0.8123    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1184   -0.2765    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8219   -0.7075    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8681    0.1162    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5691   -0.3579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3084   -0.7241    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1945    0.0930    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9194   -0.1698    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7448    0.6365    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7050   -0.4218    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8795   -1.2281    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2685   -1.7824    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4431   -2.5887    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8321   -3.1431    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0067   -3.9494    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0465   -2.8911    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4829   -1.5305    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7173   -2.3215    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9614   -2.1697    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1364   -2.1605    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6293   -1.5097    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
  2  4  1  0  0  0  0
  4  5  1  0  0  0  0
  4  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  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
 11 13  1  0  0  0  0
 13 14  2  0  0  0  0
 13 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 19 21  1  0  0  0  0
 17 22  1  0  0  0  0
 11 22  1  0  0  0  0
 22 23  1  0  0  0  0
 22 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  2  0  0  0  0
  4 26  1  0  0  0  0
  8 26  1  0  0  0  0
M  END


  Mrv1533004181502232D          

 26 28  0  0  0  0            999 V2000
   -0.5826   -1.2410    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0158   -1.8088    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1767   -2.6111    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8068   -1.5745    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9572   -2.3857    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4911   -0.8123    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1184   -0.2765    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8219   -0.7075    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8681    0.1162    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5691   -0.3579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3084   -0.7241    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1945    0.0930    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9194   -0.1698    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7448    0.6365    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7050   -0.4218    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8795   -1.2281    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2685   -1.7824    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4431   -2.5887    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8321   -3.1431    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0067   -3.9494    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0465   -2.8911    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4829   -1.5305    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7173   -2.3215    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9614   -2.1697    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1364   -2.1605    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6293   -1.5097    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
  2  4  1  0  0  0  0
  4  5  1  0  0  0  0
  4  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  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
 11 13  1  0  0  0  0
 13 14  2  0  0  0  0
 13 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 19 21  1  0  0  0  0
 17 22  1  0  0  0  0
 11 22  1  0  0  0  0
 22 23  1  0  0  0  0
 22 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  2  0  0  0  0
  4 26  1  0  0  0  0
  8 26  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0273933

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)C1(O)CCC2(C)CC3(O)C(=C)CCC(OC(C)=O)C3(C)CC=C12

> <INCHI_IDENTIFIER>
InChI=1S/C22H34O4/c1-14(2)21(24)12-11-19(5)13-22(25)15(3)7-8-18(26-16(4)23)20(22,6)10-9-17(19)21/h9,14,18,24-25H,3,7-8,10-13H2,1-2,4-6H3

> <INCHI_KEY>
OSLRAIGSKXDEKP-UHFFFAOYSA-N

> <FORMULA>
C22H34O4

> <MOLECULAR_WEIGHT>
362.51

> <EXACT_MASS>
362.245709575

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
60

> <JCHEM_AVERAGE_POLARIZABILITY>
41.4306262859243

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
1,4a-dihydroxy-3a,8a-dimethyl-5-methylidene-1-(propan-2-yl)-1H,2H,3H,3aH,4H,4aH,5H,6H,7H,8H,8aH,9H-cyclohexa[f]azulen-8-yl acetate

> <ALOGPS_LOGP>
4.46

> <JCHEM_LOGP>
2.944382135

> <ALOGPS_LOGS>
-3.97

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.743576201293113

> <JCHEM_PKA_STRONGEST_BASIC>
-0.4560704457849226

> <JCHEM_POLAR_SURFACE_AREA>
66.75999999999999

> <JCHEM_REFRACTIVITY>
101.9167

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.91e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
1,4a-dihydroxy-1-isopropyl-3a,8a-dimethyl-5-methylidene-2H,3H,4H,6H,7H,8H,9H-cyclohexa[f]azulen-8-yl acetate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 18-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   18-APR-15         0                                  
HETATM    1  C   UNK     0      -1.088  -2.316   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.030  -3.377   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -0.330  -4.874   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.506  -2.939   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0       1.787  -4.453   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       0.917  -1.516   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.088  -0.516   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       3.401  -1.321   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       3.487   0.217   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.796  -0.668   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       6.176  -1.352   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       5.963   0.174   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       7.316  -0.317   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       6.990   1.188   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       8.783  -0.787   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       9.108  -2.292   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       7.968  -3.327   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       8.294  -4.832   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       7.153  -5.867   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       7.479  -7.372   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       5.687  -5.397   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       6.501  -2.857   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       6.939  -4.333   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       5.528  -4.050   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       3.988  -4.033   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       3.041  -2.818   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5    6   26                                             
CONECT    5    4                                                            
CONECT    6    4    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9   10   26                                             
CONECT    9    8                                                            
CONECT   10    8   11                                                       
CONECT   11   10   12   13   22                                             
CONECT   12   11                                                            
CONECT   13   11   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18   22                                                  
CONECT   18   17   19                                                       
CONECT   19   18   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19                                                            
CONECT   22   17   11   23   24                                             
CONECT   23   22                                                            
CONECT   24   22   25                                                       
CONECT   25   24   26                                                       
CONECT   26   25    4    8                                                  
MASTER        0    0    0    0    0    0    0    0   26    0   56    0
END

View in JSmol

Synonyms

Value	Source
1,4a-Dihydroxy-3a,8a-dimethyl-5-methylidene-1-(propan-2-yl)-1H,2H,3H,3ah,4H,4ah,5H,6H,7H,8H,8ah,9H-cyclohexa[F]azulen-8-yl acetic acid	Generator

Chemical Formula

C₂₂H₃₄O₄

Average Mass

362.5100 Da

Monoisotopic Mass

362.24571 Da

IUPAC Name

1,4a-dihydroxy-3a,8a-dimethyl-5-methylidene-1-(propan-2-yl)-1H,2H,3H,3aH,4H,4aH,5H,6H,7H,8H,8aH,9H-cyclohexa[f]azulen-8-yl acetate

Traditional Name

1,4a-dihydroxy-1-isopropyl-3a,8a-dimethyl-5-methylidene-2H,3H,4H,6H,7H,8H,9H-cyclohexa[f]azulen-8-yl acetate

CAS Registry Number

Not Available

SMILES

CC(C)C1(O)CCC2(C)CC3(O)C(=C)CCC(OC(C)=O)C3(C)CC=C12

InChI Identifier

InChI=1S/C22H34O4/c1-14(2)21(24)12-11-19(5)13-22(25)15(3)7-8-18(26-16(4)23)20(22,6)10-9-17(19)21/h9,14,18,24-25H,3,7-8,10-13H2,1-2,4-6H3

InChI Key

OSLRAIGSKXDEKP-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Canistrocarpus cervicornis	LOTUS Database	35616633
Dictyota divaricata	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as diterpenoids. These are terpene compounds formed by four isoprene units.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Diterpenoids

Direct Parent

Diterpenoids

Alternative Parents

Substituents

Dolastane diterpenoid
Diterpenoid
Tertiary alcohol
Cyclic alcohol
Carboxylic acid ester
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
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	4.46	ALOGPS
logP	2.94	ChemAxon
logS	-4	ALOGPS
pKa (Strongest Acidic)	13.74	ChemAxon
pKa (Strongest Basic)	-0.46	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	66.76 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	101.92 m³·mol⁻¹	ChemAxon
Polarizability	41.43 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

73816995

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 1,4a-dihydroxy-1-isopropyl-3a,8a-dimethyl-5-methylidene-2h,3h,4h,6h,7h,8h,9h-cyclohexa[f]azulen-8-yl acetate (NP0273933)

MOL for NP0273933 (1,4a-dihydroxy-1-isopropyl-3a,8a-dimethyl-5-methylidene-2h,3h,4h,6h,7h,8h,9h-cyclohexa[f]azulen-8-yl acetate)

3D MOL for NP0273933 (1,4a-dihydroxy-1-isopropyl-3a,8a-dimethyl-5-methylidene-2h,3h,4h,6h,7h,8h,9h-cyclohexa[f]azulen-8-yl acetate)

3D SDF for NP0273933 (1,4a-dihydroxy-1-isopropyl-3a,8a-dimethyl-5-methylidene-2h,3h,4h,6h,7h,8h,9h-cyclohexa[f]azulen-8-yl acetate)

3D-SDF for NP0273933 (1,4a-dihydroxy-1-isopropyl-3a,8a-dimethyl-5-methylidene-2h,3h,4h,6h,7h,8h,9h-cyclohexa[f]azulen-8-yl acetate)

PDB for NP0273933 (1,4a-dihydroxy-1-isopropyl-3a,8a-dimethyl-5-methylidene-2h,3h,4h,6h,7h,8h,9h-cyclohexa[f]azulen-8-yl acetate)

3D PDB for NP0273933 (1,4a-dihydroxy-1-isopropyl-3a,8a-dimethyl-5-methylidene-2h,3h,4h,6h,7h,8h,9h-cyclohexa[f]azulen-8-yl acetate)

SMILES for NP0273933 (1,4a-dihydroxy-1-isopropyl-3a,8a-dimethyl-5-methylidene-2h,3h,4h,6h,7h,8h,9h-cyclohexa[f]azulen-8-yl acetate)

INCHI for NP0273933 (1,4a-dihydroxy-1-isopropyl-3a,8a-dimethyl-5-methylidene-2h,3h,4h,6h,7h,8h,9h-cyclohexa[f]azulen-8-yl acetate)

Structure for NP0273933 (1,4a-dihydroxy-1-isopropyl-3a,8a-dimethyl-5-methylidene-2h,3h,4h,6h,7h,8h,9h-cyclohexa[f]azulen-8-yl acetate)

3D Structure for NP0273933 (1,4a-dihydroxy-1-isopropyl-3a,8a-dimethyl-5-methylidene-2h,3h,4h,6h,7h,8h,9h-cyclohexa[f]azulen-8-yl acetate)