NP-MRD: Showing NP-Card for 2-[(2e,4ar,4br,8ar)-4b,8,8-trimethyl-4,4a,5,6,7,8a,9,10-octahydro-3h-phenanthren-2-ylidene]-3-hydroxypropanal (NP0221882)

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Record Information

Version

2.0

Created at

2022-09-05 23:34:12 UTC

Updated at

2022-09-05 23:34:13 UTC

NP-MRD ID

NP0221882

Secondary Accession Numbers

None

Natural Product Identification

Common Name

2-[(2e,4ar,4br,8ar)-4b,8,8-trimethyl-4,4a,5,6,7,8a,9,10-octahydro-3h-phenanthren-2-ylidene]-3-hydroxypropanal

Description

(5Beta,9beta,10alpha)-17-Hydroxyabieta-8(14),13(15)-dien-16-al belongs to the class of organic compounds known as diterpenoids. These are terpene compounds formed by four isoprene units. 2-[(2e,4ar,4br,8ar)-4b,8,8-trimethyl-4,4a,5,6,7,8a,9,10-octahydro-3h-phenanthren-2-ylidene]-3-hydroxypropanal is found in Euphorbia plumerioides. Based on a literature review very few articles have been published on (5beta,9beta,10alpha)-17-Hydroxyabieta-8(14),13(15)-dien-16-al.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652309062201342D          

 22 24  0  0  1  0            999 V2000
   -0.4733   -3.0591    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3020   -2.7770    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4452   -3.5894    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1105   -2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3020   -1.3480    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1270   -1.3480    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5395   -2.0625    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.9520   -1.3480    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645   -2.0625    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.7770   -1.3480    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6020   -1.3480    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0145   -2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8395   -2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2520   -1.3480    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8395   -0.6336    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2520   -2.7770    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0770   -2.7770    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6020   -2.7770    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7770   -2.7770    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645   -3.4914    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5395   -3.4914    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1270   -2.7770    0.0000 C   0  0  2  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
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  6  0  0  0
  7  9  1  0  0  0  0
  9 10  1  6  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 13 16  1  0  0  0  0
 16 17  1  0  0  0  0
 12 18  1  0  0  0  0
 18 19  2  0  0  0  0
  9 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 22 21  1  6  0  0  0
  2 22  1  0  0  0  0
  7 22  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0221882

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1(C)CCC[C@@]2(C)[C@@H]3CC\C(C=C3CC[C@H]12)=C(\CO)C=O

> <INCHI_IDENTIFIER>
InChI=1S/C20H30O2/c1-19(2)9-4-10-20(3)17-7-5-14(16(12-21)13-22)11-15(17)6-8-18(19)20/h11-12,17-18,22H,4-10,13H2,1-3H3/b16-14-/t17-,18-,20+/m1/s1

> <INCHI_KEY>
DZRCZGSKSCJAQO-LQSIBPKLSA-N

> <FORMULA>
C20H30O2

> <MOLECULAR_WEIGHT>
302.458

> <EXACT_MASS>
302.224580206

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
52

> <JCHEM_AVERAGE_POLARIZABILITY>
36.10345961843852

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-[(2E,4aR,4bR,8aR)-4b,8,8-trimethyl-2,3,4,4a,4b,5,6,7,8,8a,9,10-dodecahydrophenanthren-2-ylidene]-3-hydroxypropanal

> <JCHEM_LOGP>
3.469519826666667

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.957941884610303

> <JCHEM_PKA_STRONGEST_BASIC>
-2.8171962196714526

> <JCHEM_POLAR_SURFACE_AREA>
37.3

> <JCHEM_REFRACTIVITY>
91.7969

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
2-[(2E,4aR,4bR,8aR)-4b,8,8-trimethyl-4,4a,5,6,7,8a,9,10-octahydro-3H-phenanthren-2-ylidene]-3-hydroxypropanal

> <JCHEM_VEBER_RULE>
1

$$$$

HEADER    PROTEIN                                 06-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-SEP-22         0                                  
HETATM    1  C   UNK     0      -0.883  -5.710   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.564  -5.184   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.831  -6.700   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -0.206  -3.850   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.564  -2.516   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.104  -2.516   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.874  -3.850   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       3.644  -2.516   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.414  -3.850   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.184  -2.516   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       6.724  -2.516   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       7.494  -3.850   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       9.034  -3.850   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       9.804  -2.516   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       9.034  -1.183   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       9.804  -5.184   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      11.344  -5.184   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       6.724  -5.184   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       5.184  -5.184   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       4.414  -6.517   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       2.874  -6.517   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       2.104  -5.184   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    4   22                                             
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8    9   22                                             
CONECT    8    7                                                            
CONECT    9    7   10   19                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13   18                                                  
CONECT   13   12   14   16                                                  
CONECT   14   13   15                                                       
CONECT   15   14                                                            
CONECT   16   13   17                                                       
CONECT   17   16                                                            
CONECT   18   12   19                                                       
CONECT   19   18    9   20                                                  
CONECT   20   19   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21    2    7                                                  
MASTER        0    0    0    0    0    0    0    0   22    0   48    0
END

View in JSmol

Synonyms

Value	Source
(5b,9b,10a)-17-Hydroxyabieta-8(14),13(15)-dien-16-al	Generator
(5Β,9β,10α)-17-hydroxyabieta-8(14),13(15)-dien-16-al	Generator

Chemical Formula

C₂₀H₃₀O₂

Average Mass

302.4580 Da

Monoisotopic Mass

302.22458 Da

IUPAC Name

2-[(2E,4aR,4bR,8aR)-4b,8,8-trimethyl-2,3,4,4a,4b,5,6,7,8,8a,9,10-dodecahydrophenanthren-2-ylidene]-3-hydroxypropanal

Traditional Name

2-[(2E,4aR,4bR,8aR)-4b,8,8-trimethyl-4,4a,5,6,7,8a,9,10-octahydro-3H-phenanthren-2-ylidene]-3-hydroxypropanal

CAS Registry Number

Not Available

SMILES

CC1(C)CCC[C@@]2(C)[C@@H]3CC\C(C=C3CC[C@H]12)=C(\CO)C=O

InChI Identifier

InChI=1S/C20H30O2/c1-19(2)9-4-10-20(3)17-7-5-14(16(12-21)13-22)11-15(17)6-8-18(19)20/h11-12,17-18,22H,4-10,13H2,1-3H3/b16-14-/t17-,18-,20+/m1/s1

InChI Key

DZRCZGSKSCJAQO-LQSIBPKLSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Euphorbia plumerioides	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

Diterpenoid
Abietane diterpenoid
Phenanthrene
Hydrophenanthrene
Enal
Alpha,beta-unsaturated aldehyde
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Primary alcohol
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	3.47	ChemAxon
pKa (Strongest Acidic)	14.96	ChemAxon
pKa (Strongest Basic)	-2.8	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	37.3 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	91.8 m³·mol⁻¹	ChemAxon
Polarizability	36.1 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	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

102056139

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 2-[(2e,4ar,4br,8ar)-4b,8,8-trimethyl-4,4a,5,6,7,8a,9,10-octahydro-3h-phenanthren-2-ylidene]-3-hydroxypropanal (NP0221882)

MOL for NP0221882 (2-[(2e,4ar,4br,8ar)-4b,8,8-trimethyl-4,4a,5,6,7,8a,9,10-octahydro-3h-phenanthren-2-ylidene]-3-hydroxypropanal)

3D MOL for NP0221882 (2-[(2e,4ar,4br,8ar)-4b,8,8-trimethyl-4,4a,5,6,7,8a,9,10-octahydro-3h-phenanthren-2-ylidene]-3-hydroxypropanal)

3D SDF for NP0221882 (2-[(2e,4ar,4br,8ar)-4b,8,8-trimethyl-4,4a,5,6,7,8a,9,10-octahydro-3h-phenanthren-2-ylidene]-3-hydroxypropanal)

3D-SDF for NP0221882 (2-[(2e,4ar,4br,8ar)-4b,8,8-trimethyl-4,4a,5,6,7,8a,9,10-octahydro-3h-phenanthren-2-ylidene]-3-hydroxypropanal)

PDB for NP0221882 (2-[(2e,4ar,4br,8ar)-4b,8,8-trimethyl-4,4a,5,6,7,8a,9,10-octahydro-3h-phenanthren-2-ylidene]-3-hydroxypropanal)

3D PDB for NP0221882 (2-[(2e,4ar,4br,8ar)-4b,8,8-trimethyl-4,4a,5,6,7,8a,9,10-octahydro-3h-phenanthren-2-ylidene]-3-hydroxypropanal)

SMILES for NP0221882 (2-[(2e,4ar,4br,8ar)-4b,8,8-trimethyl-4,4a,5,6,7,8a,9,10-octahydro-3h-phenanthren-2-ylidene]-3-hydroxypropanal)

INCHI for NP0221882 (2-[(2e,4ar,4br,8ar)-4b,8,8-trimethyl-4,4a,5,6,7,8a,9,10-octahydro-3h-phenanthren-2-ylidene]-3-hydroxypropanal)

Structure for NP0221882 (2-[(2e,4ar,4br,8ar)-4b,8,8-trimethyl-4,4a,5,6,7,8a,9,10-octahydro-3h-phenanthren-2-ylidene]-3-hydroxypropanal)

3D Structure for NP0221882 (2-[(2e,4ar,4br,8ar)-4b,8,8-trimethyl-4,4a,5,6,7,8a,9,10-octahydro-3h-phenanthren-2-ylidene]-3-hydroxypropanal)