NP-MRD: Showing NP-Card for 7,13-Abietadien-18-oic acid (NP0050542)

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Record Information

Version

2.0

Created at

2022-04-27 21:56:21 UTC

Updated at

2022-04-27 21:56:21 UTC

NP-MRD ID

NP0050542

Secondary Accession Numbers

None

Natural Product Identification

Common Name

7,13-Abietadien-18-oic acid

Description

Abietic acid, also known as sylvic acid or sylvate, belongs to the class of organic compounds known as diterpenoids. These are terpene compounds formed by four isoprene units. 7,13-Abietadien-18-oic acid is found in Abies alba Mill. , Abies grandis, Abies nordmanniana, Abies pinsapo, Abies sibirica, Abies spectabilis, Agathis australis, Agathis macrophylla, Araucaria angustifolia, Arctotis arctotoides, Calamus draco, Cedrus atlantica, Cedrus libani, Ceroplastes pseudoceriferus, Commiphora myrrha , Juniperus phoenicea , Juniperus thurifera, Juniperus thurifera var.africana, Larix gmelinii, Larix gmelinii, Larix kaempferi, Liquidambar orientalis, Picea glehnii L., Picea jezoensis, Picea ajanensis, Picea koraiensis, Picea obovata, Sitka spruce, Pimenta racemosa, Pinus brutia, Pinus contorta , Pinus densiflora, Pinus grandis, Pinus heldreichii, Pinus massoniana, Pinus merkusii, Pinus nigra, Pinus palustris, Pinus pinaster, Pinus ponderosa, Pinus pumila, Pinus resinosa, Pinus sibirica, Pinus strobus, Pinus taeda, Pinus yunnanensis and Pseudotsuga menziesii. 7,13-Abietadien-18-oic acid was first documented in 2014 (PMID: 25104764). Abietic acid is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral.

Structure

MOL SDF PDB SMILES InChI

  Mrv1652309272007372D          

 24 26  0  0  0  0            999 V2000
10011.687110013.2090    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10014.546710014.0339    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10015.262210013.6215    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10014.546710014.8589    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10012.403710011.9725    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
10010.973510012.7968    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10010.259210012.3842    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10011.688010012.3842    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
10012.402310012.7967    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
10012.402310011.1467    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10013.116810011.5591    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10013.116810012.3841    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10013.117410014.0339    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10012.402910013.6215    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10013.831910012.7965    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10013.831910013.6215    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10011.687610010.8458    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
10010.258710011.5593    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10011.688510011.5593    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
10010.456810010.5021    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10011.500110010.5121    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10010.973510011.1466    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
10009.640310010.6273    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10010.756610009.7324    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 24  2  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>
NP0050542

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C20H30O2/c1-13(2)14-6-8-16-15(12-14)7-9-17-19(16,3)10-5-11-20(17,4)18(21)22/h7,12-13,16-17H,5-6,8-11H2,1-4H3,(H,21,22)/t16-,17+,19+,20+/m0/s1

> <INCHI_KEY>
RSWGJHLUYNHPMX-ONCXSQPRSA-N

> <FORMULA>
C20H30O2

> <MOLECULAR_WEIGHT>
302.451

> <EXACT_MASS>
302.224580204

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
52

> <JCHEM_AVERAGE_POLARIZABILITY>
36.39183641249039

> <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-decahydrophenanthrene-1-carboxylic acid

> <ALOGPS_LOGP>
5.28

> <JCHEM_LOGP>
4.952565060333334

> <ALOGPS_LOGS>
-4.46

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.589813146961616

> <JCHEM_POLAR_SURFACE_AREA>
37.3

> <JCHEM_REFRACTIVITY>
91.21419999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.05e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
abietic acid

> <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    8688.4838691.323   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0    8693.8208692.863   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0    8695.1568692.093   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0    8693.8208694.403   0.000  0.00  0.00           C+0
HETATM    5  H   UNK     0    8689.8208689.015   0.000  0.00  0.00           H+0
HETATM    6  C   UNK     0    8687.1518690.554   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0    8685.8178689.784   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0    8688.4848689.784   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0    8689.8188690.554   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0    8689.8188687.474   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0    8691.1518688.244   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0    8691.1518689.784   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0    8691.1528692.863   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0    8689.8198692.093   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0    8692.4868690.553   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0    8692.4868692.093   0.000  0.00  0.00           C+0
HETATM   17  H   UNK     0    8688.4848686.912   0.000  0.00  0.00           H+0
HETATM   18  C   UNK     0    8685.8168688.244   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0    8688.4858688.244   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0    8686.1868686.271   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0    8688.1338686.289   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0    8687.1518687.474   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0    8684.6628686.504   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0    8686.7468684.834   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   24   23                                                  
CONECT   21   22                                                            
CONECT   22   20   21   18   19                                             
CONECT   23   20                                                            
CONECT   24   20                                                            
MASTER        0    0    0    0    0    0    0    0   24    0   52    0
END

View in JSmol

Synonyms

Value	Source
(1R,4AR,10ar)-1,4a-dimethyl-7-(propan-2-yl)-1,2,3,4,4a,5,6,10,10a-decahydrophenanthrene-1-carboxylic acid	ChEBI
13-Isopropylpodocarpa-7,13-dien-15-Oic acid	ChEBI
7,13-Abietadien-18-Oic acid	ChEBI
Sylvic acid	ChEBI
Abieta-7,13-dien-18-Oate	Kegg
(1R,4AR,10ar)-1,4a-dimethyl-7-(propan-2-yl)-1,2,3,4,4a,5,6,10,10a-decahydrophenanthrene-1-carboxylate	Generator
13-Isopropylpodocarpa-7,13-dien-15-Oate	Generator
7,13-Abietadien-18-Oate	Generator
Sylvate	Generator
Abieta-7,13-dien-18-Oic acid	Generator
Abietate	Generator
Abietic acid, 2-aminoethanol	MeSH
Abietic acid, barium salt	MeSH
Abietic acid, palladium (+2) salt	MeSH
Abietic acid, potassium salt	MeSH
Abietic acid, sodium salt	MeSH
Abietic acid, strontium salt	MeSH
Abietic acid, zinc salt	MeSH
Abietic acid, ammonium salt	MeSH
Abietic acid, calcium salt	MeSH
Abietic acid, cobalt salt	MeSH
Abietic acid, copper salt	MeSH
(-)-Abietic acid	PhytoBank

Chemical Formula

C₂₀H₃₀O₂

Average Mass

302.4510 Da

Monoisotopic Mass

302.22458 Da

IUPAC Name

(1R,4aR,4bR,10aR)-1,4a-dimethyl-7-(propan-2-yl)-1,2,3,4,4a,4b,5,6,10,10a-decahydrophenanthrene-1-carboxylic acid

Traditional Name

abietic acid

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C20H30O2/c1-13(2)14-6-8-16-15(12-14)7-9-17-19(16,3)10-5-11-20(17,4)18(21)22/h7,12-13,16-17H,5-6,8-11H2,1-4H3,(H,21,22)/t16-,17+,19+,20+/m0/s1

InChI Key

RSWGJHLUYNHPMX-ONCXSQPRSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Abies alba	Plant	KNApSAcK
Abies grandis	LOTUS Database	35616633
Abies nordmanniana	LOTUS Database	35616633
Abies pinsapo	LOTUS Database	35616633
Abies sibirica	LOTUS Database	35616633
Abies spectabilis	LOTUS Database	35616633
Agathis australis	LOTUS Database	35616633
Agathis macrophylla	LOTUS Database	35616633
Araucaria angustifolia	Plant	KNApSAcK
Arctotis arctotoides	LOTUS Database	35616633
Calamus draco	LOTUS Database	35616633
Cedrus atlantica	LOTUS Database	35616633
Cedrus libani	LOTUS Database	35616633
Ceroplastes pseudoceriferus	LOTUS Database	35616633
Commiphora myrrha	Plant	KNApSAcK
Juniperus phoenicea	Plant	KNApSAcK
Juniperus thurifera	LOTUS Database	35616633
Juniperus thurifera var.africana	Plant	KNApSAcK
Larix gmelini	LOTUS Database	35616633
Larix gmelinii var. olgensis	LOTUS Database	35616633
Larix kaempferi	LOTUS Database	35616633
Liquidambar orientalis	LOTUS Database	35616633
Picea glehnii L.	Plant	KNApSAcK
Picea jezoensis	LOTUS Database	35616633
Picea jezoensis var. jezoensis	Plant	KNApSAcK
Picea koraiensis	Plant	KNApSAcK
Picea obovata	LOTUS Database	35616633
Picea sitchensis	-	KNApSAcK
Pimenta racemosa	LOTUS Database	35616633
Pinus brutia	LOTUS Database	35616633
Pinus contorta	Plant	KNApSAcK
Pinus densiflora	LOTUS Database	35616633
Pinus grandis	Plant	KNApSAcK
Pinus heldreichii	LOTUS Database	35616633
Pinus massoniana	Plant	KNApSAcK
Pinus merkusii	LOTUS Database	35616633
Pinus nigra	LOTUS Database	35616633
Pinus palustris	LOTUS Database	35616633
Pinus pinaster	LOTUS Database	35616633
Pinus ponderosa	LOTUS Database	35616633
Pinus pumila	LOTUS Database	35616633
Pinus resinosa	LOTUS Database	35616633
Pinus sibirica	Plant	KNApSAcK
Pinus strobus	LOTUS Database	35616633
Pinus taeda	Plant	KNApSAcK
Pinus yunnanensis	LOTUS Database	35616633
Pseudotsuga menziesii	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
Monocarboxylic acid or derivatives
Carboxylic acid
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

monocarboxylic acid (CHEBI:28987 )
abietane diterpenoid (CHEBI:28987 )
Abietane diterpenoids (C06087 )
Abietanes (C06087 )
Abietane diterpenoids (LMPR0104050001 )

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	5.28	ALOGPS
logP	4.95	ChemAxon
logS	-4.5	ALOGPS
pKa (Strongest Acidic)	4.59	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	37.3 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	91.21 m³·mol⁻¹	ChemAxon
Polarizability	36.39 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

C00000871

Chemspider ID

Not Available

KEGG Compound ID

C06087

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Abietic_acid

METLIN ID

Not Available

PubChem Compound

10569

PDB ID

Not Available

ChEBI ID

28987

Good Scents ID

Not Available

References

General References

Zhu Y, Zhang S, Geng Z, Wang D, Liu F, Zhang M, Bian H, Xu W: Analysis of abietic acid and dehydroabietic acid residues in raw ducks and cooked ducks. Poult Sci. 2014 Oct;93(10):2663-7. doi: 10.3382/ps.2014-04045. Epub 2014 Aug 7. [PubMed:25104764 ]

Showing NP-Card for 7,13-Abietadien-18-oic acid (NP0050542)

MOL for NP0050542 (7,13-Abietadien-18-oic acid)

3D MOL for NP0050542 (7,13-Abietadien-18-oic acid)

3D SDF for NP0050542 (7,13-Abietadien-18-oic acid)

3D-SDF for NP0050542 (7,13-Abietadien-18-oic acid)

PDB for NP0050542 (7,13-Abietadien-18-oic acid)

3D PDB for NP0050542 (7,13-Abietadien-18-oic acid)

SMILES for NP0050542 (7,13-Abietadien-18-oic acid)

INCHI for NP0050542 (7,13-Abietadien-18-oic acid)

Structure for NP0050542 (7,13-Abietadien-18-oic acid)

3D Structure for NP0050542 (7,13-Abietadien-18-oic acid)