NP-MRD: Showing NP-Card for Abieta-7,13-diene-18-ol (NP0050541)

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Record Information

Version

2.0

Created at

2022-04-27 21:56:20 UTC

Updated at

2022-04-27 21:56:20 UTC

NP-MRD ID

NP0050541

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Abieta-7,13-diene-18-ol

Description

Abietol, also known as abietadienol or abietyl alcohol, belongs to the class of organic compounds known as diterpenoids. These are terpene compounds formed by four isoprene units. Thus, abietol is considered to be an isoprenoid lipid molecule. Abieta-7,13-diene-18-ol is found in Abies firma, Abies nordmanniana, Abies pinsapo, Abies sibirica, Cedrus atlantica, Juniperus phoenicea , Juniperus sabina, Juniperus thurifera, Juniperus thurifera var.africana, Larix gmelinii, Larix kaempferi, Pinus contorta , Pinus grandis, Pinus koraiensis , Pinus sibirica and Pinus sylvestris . Abieta-7,13-diene-18-ol was first documented in 2001 (PMID: 11182488). Abietol is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral (PMID: 22459455).

Structure

MOL SDF PDB SMILES InChI


  Mrv1652309272006262D          

 23 25  0  0  0  0            999 V2000
10010.438610011.9605    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10013.298010012.7854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10014.013610012.3729    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10013.298010013.6104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10011.155110010.7239    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
10009.725010011.5482    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10009.010610011.1356    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10010.439510011.1356    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
10011.153710011.5481    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
10011.153710009.8981    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10011.868110010.3105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10011.868110011.1355    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10011.868710012.7854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10011.154310012.3729    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10012.583210011.5479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10012.583210012.3729    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10010.439110009.5972    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
10009.010110010.3107    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10010.440010010.3107    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
10009.208210009.2534    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10010.251510009.2635    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10009.725010009.8980    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
10008.391710009.3787    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  3  1  0  0  0  0
  2  4  1  0  0  0  0
  6  7  1  0  0  0  0
  6  8  1  0  0  0  0
  9 12  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 13 14  1  0  0  0  0
 13 16  1  0  0  0  0
 15 16  2  0  0  0  0
 16  2  1  0  0  0  0
 14  9  1  0  0  0  0
  9  5  1  6  0  0  0
 12 15  1  0  0  0  0
  9  8  1  0  0  0  0
  8  1  1  1  0  0  0
 19 17  1  6  0  0  0
  7 18  1  0  0  0  0
 19  8  1  0  0  0  0
 19 10  1  0  0  0  0
 22 20  1  6  0  0  0
 22 21  1  0  0  0  0
 20 23  1  0  0  0  0
 18 22  1  0  0  0  0
 22 19  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0050541

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H][C@]12CCC(=CC1=CC[C@@]1([H])[C@](C)(CO)CCC[C@]21C)C(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C20H32O/c1-14(2)15-6-8-17-16(12-15)7-9-18-19(3,13-21)10-5-11-20(17,18)4/h7,12,14,17-18,21H,5-6,8-11,13H2,1-4H3/t17-,18-,19-,20+/m0/s1

> <INCHI_KEY>
GQRUHVMVWNKUFW-LWYYNNOASA-N

> <FORMULA>
C20H32O

> <MOLECULAR_WEIGHT>
288.475

> <EXACT_MASS>
288.24531565

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_ATOM_COUNT>
53

> <JCHEM_AVERAGE_POLARIZABILITY>
36.08779662231689

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
[(1R,4aR,4bR,10aR)-1,4a-dimethyl-7-(propan-2-yl)-1,2,3,4,4a,4b,5,6,10,10a-decahydrophenanthren-1-yl]methanol

> <ALOGPS_LOGP>
5.72

> <JCHEM_LOGP>
4.480101304666667

> <ALOGPS_LOGS>
-4.59

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
18.65208138301447

> <JCHEM_PKA_STRONGEST_BASIC>
-1.201379603069471

> <JCHEM_POLAR_SURFACE_AREA>
20.23

> <JCHEM_REFRACTIVITY>
91.2717

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
7.39e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
abietyl alcohol

> <JCHEM_VEBER_RULE>
1

$$$$

HEADER    PROTEIN                                 27-SEP-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-SEP-20         0                                  
HETATM    1  C   UNK     0    8686.1528688.993   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0    8691.4908690.533   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0    8692.8258689.763   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0    8691.4908692.073   0.000  0.00  0.00           C+0
HETATM    5  H   UNK     0    8687.4898686.685   0.000  0.00  0.00           H+0
HETATM    6  C   UNK     0    8684.8208688.223   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0    8683.4868687.453   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0    8686.1548687.453   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0    8687.4878688.223   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0    8687.4878685.143   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0    8688.8218685.913   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0    8688.8218687.453   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0    8688.8228690.533   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0    8687.4888689.763   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0    8690.1558688.223   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0    8690.1558689.763   0.000  0.00  0.00           C+0
HETATM   17  H   UNK     0    8686.1538684.581   0.000  0.00  0.00           H+0
HETATM   18  C   UNK     0    8683.4858685.913   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0    8686.1558685.913   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0    8683.8558683.940   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0    8685.8038683.958   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0    8684.8208685.143   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0    8682.3318684.174   0.000  0.00  0.00           O+0
CONECT    1    8                                                            
CONECT    2    3    4   16                                                  
CONECT    3    2                                                            
CONECT    4    2                                                            
CONECT    5    9                                                            
CONECT    6    7    8                                                       
CONECT    7    6   18                                                       
CONECT    8    6    9    1   19                                             
CONECT    9   12   14    5    8                                             
CONECT   10   11   19                                                       
CONECT   11   10   12                                                       
CONECT   12    9   11   15                                                  
CONECT   13   14   16                                                       
CONECT   14   13    9                                                       
CONECT   15   16   12                                                       
CONECT   16   13   15    2                                                  
CONECT   17   19                                                            
CONECT   18    7   22                                                       
CONECT   19   17    8   10   22                                             
CONECT   20   22   23                                                       
CONECT   21   22                                                            
CONECT   22   20   21   18   19                                             
CONECT   23   20                                                            
MASTER        0    0    0    0    0    0    0    0   23    0   50    0
END

View in JSmol

Synonyms

Value	Source
Abieta-7,13-dien-18-ol	ChEBI
Abietadienol	ChEBI
Abietinol	ChEBI
Abietyl alcohol	ChEBI
((1R,4AR,4BR,10ar)-7-isopropyl-1,4a-dimethyl-1,2,3,4,4a,4b,5,6,10,10a-decahydrophenanthren-1-yl)methanol	Kegg

Chemical Formula

C₂₀H₃₂O

Average Mass

288.4750 Da

Monoisotopic Mass

288.24532 Da

IUPAC Name

[(1R,4aR,4bR,10aR)-1,4a-dimethyl-7-(propan-2-yl)-1,2,3,4,4a,4b,5,6,10,10a-decahydrophenanthren-1-yl]methanol

Traditional Name

abietyl alcohol

CAS Registry Number

Not Available

SMILES

[H][C@]12CCC(=CC1=CC[C@@]1([H])[C@](C)(CO)CCC[C@]21C)C(C)C

InChI Identifier

InChI=1S/C20H32O/c1-14(2)15-6-8-17-16(12-15)7-9-18-19(3,13-21)10-5-11-20(17,18)4/h7,12,14,17-18,21H,5-6,8-11,13H2,1-4H3/t17-,18-,19-,20+/m0/s1

InChI Key

GQRUHVMVWNKUFW-LWYYNNOASA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Abies firma	LOTUS Database	35616633
Abies nordmanniana	LOTUS Database	35616633
Abies pinsapo	LOTUS Database	35616633
Abies sibirica	LOTUS Database	35616633
Cedrus atlantica	LOTUS Database	35616633
Juniperus phoenicea	Plant	KNApSAcK
Juniperus sabina	LOTUS Database	35616633
Juniperus thurifera	LOTUS Database	35616633
Juniperus thurifera var.africana	Plant	KNApSAcK
Larix gmelini	LOTUS Database	35616633
Larix kaempferi	LOTUS Database	35616633
Pinus contorta	Plant	KNApSAcK
Pinus grandis	Plant	KNApSAcK
Pinus koraiensis	Plant	KNApSAcK
Pinus sibirica	Plant	KNApSAcK
Pinus sylvestris	Plant	KNApSAcK

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
Organic oxygen compound
Hydrocarbon derivative
Primary alcohol
Organooxygen compound
Alcohol
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

abietane diterpenoid (CHEBI:29510 )
Abietane diterpenoids (C11882 )
Abietane diterpenoids (LMPR0104050006 )

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	5.72	ALOGPS
logP	4.48	ChemAxon
logS	-4.6	ALOGPS
pKa (Strongest Acidic)	18.65	ChemAxon
pKa (Strongest Basic)	-1.2	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	20.23 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	91.27 m³·mol⁻¹	ChemAxon
Polarizability	36.09 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

C00000870

Chemspider ID

391688

KEGG Compound ID

C11882

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

443474

PDB ID

Not Available

ChEBI ID

29510

Good Scents ID

Not Available

References

General References

Alqasoumi SI, Abdel-Kader MS: Terpenoids from Juniperus procera with hepatoprotective activity. Pak J Pharm Sci. 2012 Apr;25(2):315-22. [PubMed:22459455 ]
Angelopoulou D, Demetzos C, Perdetzoglou D: An interpopulation study of the essential oils of Cistus parviflorus L. growing in Crete (Greece). Biochem Syst Ecol. 2001 Apr;29(4):405-415. doi: 10.1016/s0305-1978(00)00071-5. [PubMed:11182488 ]

Showing NP-Card for Abieta-7,13-diene-18-ol (NP0050541)

MOL for NP0050541 (Abieta-7,13-diene-18-ol)

3D MOL for NP0050541 (Abieta-7,13-diene-18-ol)

3D SDF for NP0050541 (Abieta-7,13-diene-18-ol)

3D-SDF for NP0050541 (Abieta-7,13-diene-18-ol)

PDB for NP0050541 (Abieta-7,13-diene-18-ol)

3D PDB for NP0050541 (Abieta-7,13-diene-18-ol)

SMILES for NP0050541 (Abieta-7,13-diene-18-ol)

INCHI for NP0050541 (Abieta-7,13-diene-18-ol)

Structure for NP0050541 (Abieta-7,13-diene-18-ol)

3D Structure for NP0050541 (Abieta-7,13-diene-18-ol)