Abietic acid

Details

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Internal ID 5ca387aa-765a-4bd8-86df-06dbb2c96bea
Taxonomy Lipids and lipid-like molecules > Prenol lipids > Diterpenoids
IUPAC Name (1R,4aR,4bR,10aR)-1,4a-dimethyl-7-propan-2-yl-2,3,4,4b,5,6,10,10a-octahydrophenanthrene-1-carboxylic acid
SMILES (Canonical) CC(C)C1=CC2=CCC3C(C2CC1)(CCCC3(C)C(=O)O)C
SMILES (Isomeric) CC(C)C1=CC2=CC[C@@H]3[C@@]([C@H]2CC1)(CCC[C@@]3(C)C(=O)O)C
InChI 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
Popularity 1,273 references in papers

Physical and Chemical Properties

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Molecular Formula C20H30O2
Molecular Weight 302.50 g/mol
Exact Mass 302.224580195 g/mol
Topological Polar Surface Area (TPSA) 37.30 Ų
XlogP 4.80
Atomic LogP (AlogP) 5.21
H-Bond Acceptor 1
H-Bond Donor 1
Rotatable Bonds 2

Synonyms

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514-10-3
Sylvic acid
Abietate
l-Abietic acid
Rosin Acid
7,13-Abietadien-18-oic acid
Kyselina abietova
13-Isopropylpodocarpa-7,13-dien-15-oic acid
CCRIS 3183
Abietic acid, technical
There are more than 10 synonyms. If you wish to see them all click here.

2D Structure

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2D Structure of Abietic acid

3D Structure

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ADMET Properties (via admetSAR 2)

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Target Value Probability (raw) Probability (%)
Human Intestinal Absorption + 0.9971 99.71%
Caco-2 + 0.8501 85.01%
Blood Brain Barrier + 0.7000 70.00%
Human oral bioavailability + 0.6143 61.43%
Subcellular localzation Mitochondria 0.5180 51.80%
OATP2B1 inhibitior - 0.8634 86.34%
OATP1B1 inhibitior - 0.7737 77.37%
OATP1B3 inhibitior - 0.5698 56.98%
MATE1 inhibitior - 0.9200 92.00%
OCT2 inhibitior + 0.5500 55.00%
BSEP inhibitior + 0.7884 78.84%
P-glycoprotein inhibitior - 0.8263 82.63%
P-glycoprotein substrate - 0.8345 83.45%
CYP3A4 substrate + 0.5889 58.89%
CYP2C9 substrate - 0.6168 61.68%
CYP2D6 substrate - 0.8908 89.08%
CYP3A4 inhibition - 0.9288 92.88%
CYP2C9 inhibition + 0.8611 86.11%
CYP2C19 inhibition + 0.8347 83.47%
CYP2D6 inhibition - 0.9231 92.31%
CYP1A2 inhibition - 0.8620 86.20%
CYP2C8 inhibition - 0.7966 79.66%
CYP inhibitory promiscuity - 0.8602 86.02%
UGT catelyzed - 0.0000 0.00%
Carcinogenicity (binary) - 0.8700 87.00%
Carcinogenicity (trinary) Non-required 0.6088 60.88%
Eye corrosion - 0.9780 97.80%
Eye irritation - 0.6445 64.45%
Skin irritation - 0.6792 67.92%
Skin corrosion - 0.9810 98.10%
Ames mutagenesis - 0.9754 97.54%
Human Ether-a-go-go-Related Gene inhibition - 0.4477 44.77%
Micronuclear - 0.9200 92.00%
Hepatotoxicity - 0.5551 55.51%
skin sensitisation + 0.7847 78.47%
Respiratory toxicity + 0.8333 83.33%
Reproductive toxicity + 0.6333 63.33%
Mitochondrial toxicity + 0.7375 73.75%
Nephrotoxicity - 0.7125 71.25%
Acute Oral Toxicity (c) III 0.6392 63.92%
Estrogen receptor binding - 0.5000 50.00%
Androgen receptor binding - 0.4911 49.11%
Thyroid receptor binding + 0.6946 69.46%
Glucocorticoid receptor binding + 0.7476 74.76%
Aromatase binding - 0.7430 74.30%
PPAR gamma + 0.8707 87.07%
Honey bee toxicity - 0.9235 92.35%
Biodegradation - 0.7750 77.50%
Crustacea aquatic toxicity - 0.6900 69.00%
Fish aquatic toxicity + 1.0000 100.00%

Targets

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Proven Targets:

CHEMBL ID UniProt ID Name Min activity Assay type Source
CHEMBL1293235 P02545 Prelamin-A/C 1995.3 nM
Potency
via CMAUP
CHEMBL1697668 Q9Y6L6 Solute carrier organic anion transporter family member 1B1 2691.53 nM
IC50
PMID: 23571415
CHEMBL1743121 Q9NPD5 Solute carrier organic anion transporter family member 1B3 5248.07 nM
IC50
PMID: 23571415

Predicted Targets (via Super-PRED):

CHEMBL ID UniProt ID Name Probability Model accuracy
CHEMBL4040 P28482 MAP kinase ERK2 94.89% 83.82%
CHEMBL5619 P27695 DNA-(apurinic or apyrimidinic site) lyase 94.01% 91.11%
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 92.29% 96.09%
CHEMBL253 P34972 Cannabinoid CB2 receptor 92.10% 97.25%
CHEMBL2581 P07339 Cathepsin D 89.63% 98.95%
CHEMBL4203 Q9HAZ1 Dual specificity protein kinase CLK4 89.40% 94.45%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 85.46% 95.56%
CHEMBL1994 P08235 Mineralocorticoid receptor 84.75% 100.00%
CHEMBL3137262 O60341 LSD1/CoREST complex 84.37% 97.09%
CHEMBL3359 P21462 Formyl peptide receptor 1 83.51% 93.56%
CHEMBL340 P08684 Cytochrome P450 3A4 83.16% 91.19%
CHEMBL221 P23219 Cyclooxygenase-1 81.65% 90.17%
CHEMBL4227 P25090 Lipoxin A4 receptor 80.80% 100.00%
CHEMBL5608 Q16288 NT-3 growth factor receptor 80.68% 95.89%
CHEMBL3038477 P67870 Casein kinase II alpha/beta 80.59% 99.23%

Plants that contains it

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Below are displayed all the plants proven (via scientific papers) to contain this compound!
To see more specific details click the taxa you are interested in.
Abies alba
Abies forrestii var. georgei
Abies grandis
Abies nordmanniana
Abies sibirica subsp. semenovii
Abies spectabilis
Acacia simplicifolia
Adina trichotoma
Afraegle paniculata
Agathis australis
Agathis macrophylla
Aglaia meridionalis
Allium ursinum
Ammi majus
Arcangelisia gusanlung
Arctotis arctotoides
Artemisia argyi
Artemisia schmidtiana
Asparagus racemosus
Astragalus glycyphyllos
Athrixia elata
Bowdichia virgilioides
Brickellia pendula
Brucea antidysenterica
Calamus draco
Cassinia subtropica
Cedrus libani
Centaurea cheiranthifolia
Centaurea zuccariniana
Citrus deliciosa
Cladanthus arabicus
Cladanthus scariosus
Cleidion brevipetiolatum
Colchicum arenarium
Copaifera paupera
Cousinia canescens
Cratoxylum formosum subsp. pruniflorum
Crotalaria spectabilis
Daphnandra johnsonii
Dianella revoluta
Endosamara racemosa
Entandrophragma cylindricum
Erythrina burttii
Escallonia virgata
Ficus maxima
Firmiana simplex
Gleichenia polypodioides
Gyrothyra underwoodiana
Hesperocyparis nevadensis
Hippeastrum aulicum
Jacobaea erratica
Jacobaea erucifolia subsp. argunensis
Juniperus thurifera
Kokoona ochracea
Lamprolobium fruticosum
Larix gmelinii var. gmelinii
Larix gmelinii var. olgensis
Larix kaempferi
Lathyrus linifolius
Leptospermum scoparium
Liquidambar formosana
Liquidambar orientalis
Loropetalum chinense
Machilus obovatifolia
Magnolia acuminata
Mentha pulegium
Mikania grazielae
Nauclea parva
Onoclea struthiopteris
Ophioglossum vulgatum
Phagnalon bicolor
Picea obovata
Pimenta racemosa
Pinus brutia var. pityusa
Pinus densiflora
Pinus heldreichii
Pinus massoniana
Pinus merkusii
Pinus nigra
Pinus palustris
Pinus pinaster
Pinus ponderosa
Pinus pumila
Pinus resinosa
Pinus sibirica
Pinus strobus
Pinus yunnanensis
Piper callosum
Pittocaulon bombycophole
Plectranthus amboinicus
Plumbago europaea
Polyachyrus sphaerocephalus
Prioria pinnata
Pseudoconyza viscosa
Pseudotsuga menziesii
Reissantia indica
Rhodanthe stricta
Rubus pungens
Salvia barrelieri
Sanguisorba minor
Sideritis lanata
Simmondsia chinensis
Squamopappus skutchii
Symplocos glauca
Syzygium cumini
Tabebuia rosea
Tamarix gallica
Tanacetum santolina
Teucrium scorodonia
Timonius kaniensis
Tinospora hainanensis
Titanotrichum oldhamii
Uvaria littoralis
Veronica anagallis
Viola hondoensis
Waitzia acuminata
Wrightia tinctoria

Cross-Links

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PubChem 10569
NPASS NPC309399
ChEMBL CHEMBL71893
LOTUS LTS0088895
wikiData Q321068