Dehydroabietic acid

Details

Top
Internal ID 1628acab-804a-4241-b16e-9976f32f3801
Taxonomy Lipids and lipid-like molecules > Prenol lipids > Diterpenoids
IUPAC Name (1R,4aS,10aR)-1,4a-dimethyl-7-propan-2-yl-2,3,4,9,10,10a-hexahydrophenanthrene-1-carboxylic acid
SMILES (Canonical) CC(C)C1=CC2=C(C=C1)C3(CCCC(C3CC2)(C)C(=O)O)C
SMILES (Isomeric) CC(C)C1=CC2=C(C=C1)[C@]3(CCC[C@@]([C@@H]3CC2)(C)C(=O)O)C
InChI InChI=1S/C20H28O2/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/h6,8,12-13,17H,5,7,9-11H2,1-4H3,(H,21,22)/t17-,19-,20-/m1/s1
InChI Key NFWKVWVWBFBAOV-MISYRCLQSA-N
Popularity 855 references in papers

Physical and Chemical Properties

Top
Molecular Formula C20H28O2
Molecular Weight 300.40 g/mol
Exact Mass 300.208930132 g/mol
Topological Polar Surface Area (TPSA) 37.30 Ų
XlogP 5.60
Atomic LogP (AlogP) 4.90
H-Bond Acceptor 1
H-Bond Donor 1
Rotatable Bonds 2

Synonyms

Top
1740-19-8
Dehydroabietate
(+)-Dehydroabietic acid
Abieta-8,11,13-trien-18-oic acid
Abietic acid, dehydro-
(-)-Dehydroabietic acid
13-Isopropylpodocarpa-8,11,13-trien-15-oic acid
NSC 2952
1-Phenanthrenecarboxylic acid, 1,2,3,4,4a,9,10,10a-octahydro-1,4a-dimethyl-7-(1-methylethyl)-, (1R,4aS,10aR)-
CHEBI:29571
There are more than 10 synonyms. If you wish to see them all click here.

2D Structure

Top
2D Structure of Dehydroabietic acid

3D Structure

Top

ADMET Properties (via admetSAR 2)

Top
Target Value Probability (raw) Probability (%)
Human Intestinal Absorption + 0.9974 99.74%
Caco-2 + 0.8110 81.10%
Blood Brain Barrier + 0.8250 82.50%
Human oral bioavailability + 0.5286 52.86%
Subcellular localzation Mitochondria 0.6168 61.68%
OATP2B1 inhibitior - 0.8611 86.11%
OATP1B1 inhibitior + 0.8991 89.91%
OATP1B3 inhibitior + 0.8518 85.18%
MATE1 inhibitior - 0.9400 94.00%
OCT2 inhibitior - 0.5500 55.00%
BSEP inhibitior + 0.7895 78.95%
P-glycoprotein inhibitior - 0.8317 83.17%
P-glycoprotein substrate - 0.6894 68.94%
CYP3A4 substrate + 0.5474 54.74%
CYP2C9 substrate - 0.5630 56.30%
CYP2D6 substrate - 0.8425 84.25%
CYP3A4 inhibition - 0.9308 93.08%
CYP2C9 inhibition - 0.6708 67.08%
CYP2C19 inhibition + 0.5086 50.86%
CYP2D6 inhibition - 0.8989 89.89%
CYP1A2 inhibition - 0.6448 64.48%
CYP2C8 inhibition - 0.7410 74.10%
CYP inhibitory promiscuity - 0.9408 94.08%
UGT catelyzed - 0.0000 0.00%
Carcinogenicity (binary) - 0.7611 76.11%
Carcinogenicity (trinary) Non-required 0.6380 63.80%
Eye corrosion - 0.9659 96.59%
Eye irritation - 0.8837 88.37%
Skin irritation - 0.7310 73.10%
Skin corrosion - 0.9760 97.60%
Ames mutagenesis - 0.8444 84.44%
Human Ether-a-go-go-Related Gene inhibition - 0.4437 44.37%
Micronuclear - 0.9841 98.41%
Hepatotoxicity - 0.6749 67.49%
skin sensitisation - 0.6804 68.04%
Respiratory toxicity - 0.7556 75.56%
Reproductive toxicity + 0.6667 66.67%
Mitochondrial toxicity - 0.7500 75.00%
Nephrotoxicity - 0.8954 89.54%
Acute Oral Toxicity (c) III 0.7869 78.69%
Estrogen receptor binding - 0.4744 47.44%
Androgen receptor binding + 0.5208 52.08%
Thyroid receptor binding + 0.6653 66.53%
Glucocorticoid receptor binding - 0.5074 50.74%
Aromatase binding + 0.5438 54.38%
PPAR gamma + 0.8090 80.90%
Honey bee toxicity - 0.8972 89.72%
Biodegradation - 0.9000 90.00%
Crustacea aquatic toxicity - 0.6500 65.00%
Fish aquatic toxicity + 1.0000 100.00%

Targets

Top

Proven Targets:

CHEMBL ID UniProt ID Name Min activity Assay type Source
CHEMBL5575 Q15046 Lysyl-tRNA synthetase 27.7 nM
IC50
via Super-PRED

Predicted Targets (via Super-PRED):

CHEMBL ID UniProt ID Name Probability Model accuracy
CHEMBL5619 P27695 DNA-(apurinic or apyrimidinic site) lyase 98.18% 91.11%
CHEMBL4203 Q9HAZ1 Dual specificity protein kinase CLK4 95.01% 94.45%
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 94.17% 96.09%
CHEMBL2581 P07339 Cathepsin D 93.18% 98.95%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 89.57% 95.56%
CHEMBL5845 P23415 Glycine receptor subunit alpha-1 89.15% 90.71%
CHEMBL340 P08684 Cytochrome P450 3A4 85.33% 91.19%
CHEMBL5608 Q16288 NT-3 growth factor receptor 84.91% 95.89%
CHEMBL4040 P28482 MAP kinase ERK2 84.85% 83.82%
CHEMBL253 P34972 Cannabinoid CB2 receptor 83.98% 97.25%
CHEMBL3359 P21462 Formyl peptide receptor 1 83.92% 93.56%
CHEMBL3351 Q13085 Acetyl-CoA carboxylase 1 81.23% 93.04%
CHEMBL1994 P08235 Mineralocorticoid receptor 80.47% 100.00%
CHEMBL2781 P19634 Sodium/hydrogen exchanger 1 80.25% 90.24%
CHEMBL4208 P20618 Proteasome component C5 80.14% 90.00%

Plants that contains it

Top
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 forrestii var. georgei
Abies spectabilis
Acacia simplicifolia
Adina trichotoma
Afraegle paniculata
Alcea rosea
Alpinia roxburghii
Anisochilus harmandii
Artemisia argyi
Asparagus racemosus
Astragalus glycyphyllos
Athrixia elata
Balanops australiana
Bowdichia virgilioides
Brucea antidysenterica
Cassinia subtropica
Cedrus deodara
Cedrus libani
Centaurea cheiranthifolia
Centaurea zuccariniana
Cladanthus arabicus
Colchicum arenarium
Cousinia canescens
Cratoxylum formosum subsp. pruniflorum
Daphnandra johnsonii
Davallia perdurans
Dianella revoluta
Erythrina burttii
Euonymus tingens
Euphorbia cornigera
Firmiana simplex
Gonzalezia decurrens
Gyrothyra underwoodiana
Hippeastrum aulicum
Hylocomium splendens
Isodon nervosus
Jacobaea erucifolia subsp. argunensis
Kokoona ochracea
Kokoona reflexa
Lamprolobium fruticosum
Larix decidua
Larix kaempferi
Lepechinia caulescens
Liquidambar formosana
Machilus obovatifolia
Maesa ramentacea
Maprounea guianensis
Mentha pulegium
Mikania grazielae
Millettia laurentii
Monodora tenuifolia
Nauclea parva
Ocimum tenuiflorum
Peritassa campestris
Phagnalon bicolor
Pinus densiflora
Pinus halepensis
Pinus luchuensis
Pinus massoniana
Pinus palustris
Pinus pumila
Pinus resinosa
Pinus strobus
Pinus sylvestris
Pinus taeda
Pinus yunnanensis
Piper callosum
Pittocaulon bombycophole
Pluchea odorata
Polyachyrus sphaerocephalus
Prioria pinnata
Pseudoconyza viscosa
Pseudotsuga sinensis var. sinensis
Rubus pungens
Salacia lehmbachii
Salvia barrelieri
Salvia yosgadensis
Sanguisorba minor
Sideritis brevibracteata
Sideritis lanata
Sideroxylon cubense
Squamopappus skutchii
Symplocos glauca
Syzygium cumini
Tamarix gallica
Teucrium scorodonia
Tinospora hainanensis
Titanotrichum oldhamii
Tripterygium wilfordii
Uvaria littoralis
Veronica anagallis
Viola hondoensis
Waitzia acuminata
Wrightia tinctoria

Cross-Links

Top
PubChem 94391
NPASS NPC128248
ChEMBL CHEMBL12850
LOTUS LTS0252977
wikiData Q27110153