4-Epicommunic acid

Details

• Internal ID: 59cc590a-1650-4b1b-a914-eb03b31bc165
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Diterpenoids
• IUPAC Name: (1R,4aR,5S,8aR)-1,4a-dimethyl-6-methylidene-5-[(2E)-3-methylpenta-2,4-dienyl]-3,4,5,7,8,8a-hexahydro-2H-naphthalene-1-carboxylic acid
• SMILES (Canonical): CC(=CCC1C(=C)CCC2C1(CCCC2(C)C(=O)O)C)C=C
• SMILES (Isomeric): C/C(=C\C[C@H]1C(=C)CC[C@@H]2[C@@]1(CCC[C@@]2(C)C(=O)O)C)/C=C
• InChI: InChI=1S/C20H30O2/c1-6-14(2)8-10-16-15(3)9-11-17-19(16,4)12-7-13-20(17,5)18(21)22/h6,8,16-17H,1,3,7,9-13H2,2,4-5H3,(H,21,22)/b14-8+/t16-,17+,19+,20+/m0/s1
• InChI Key: YGBZFOQXPOGACY-ONIUZDBUSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₂₀H₃₀O₂
• Molecular Weight: 302.50 g/mol
• Exact Mass: 302.224580195 g/mol
• Topological Polar Surface Area (TPSA): 37.30 Ų
• XlogP: 5.70
• Atomic LogP (AlogP): 5.37
• H-Bond Acceptor: 1
• H-Bond Donor: 1
• Rotatable Bonds: 4

Synonyms

• 83945-57-7
• trans-Ozic acid
• (1R,4AR,5S,8aR)-1,4a-dimethyl-6-methylene-5-((E)-3-methylpenta-2,4-dien-1-yl)decahydronaphthalene-1-carboxylic acid
• (1R,4aR,5S,8aR)-1,4a-dimethyl-6-methylidene-5-[(2E)-3-methylpenta-2,4-dienyl]-3,4,5,7,8,8a-hexahydro-2H-naphthalene-1-carboxylic acid
• (+)-trans-Ozic acid
• (+)-trans-Ozic acid; 4-epi-trans-Communic acid
• CHEMBL3402737
• AKOS040761135
• Labda-8(20),12,14-trien-18-oic acid

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9955	99.55%
Caco-2	+	0.8034	80.34%
Blood Brain Barrier	+	0.8000	80.00%
Human oral bioavailability	-	0.6429	64.29%
Subcellular localzation	Mitochondria	0.4306	43.06%
OATP2B1 inhibitior	-	0.8614	86.14%
OATP1B1 inhibitior	+	0.8140	81.40%
OATP1B3 inhibitior	-	0.3817	38.17%
MATE1 inhibitior	-	0.9200	92.00%
OCT2 inhibitior	-	0.5750	57.50%
BSEP inhibitior	+	0.7419	74.19%
P-glycoprotein inhibitior	-	0.8359	83.59%
P-glycoprotein substrate	-	0.7881	78.81%
CYP3A4 substrate	+	0.6317	63.17%
CYP2C9 substrate	-	0.6168	61.68%
CYP2D6 substrate	-	0.8908	89.08%
CYP3A4 inhibition	-	0.7540	75.40%
CYP2C9 inhibition	+	0.5318	53.18%
CYP2C19 inhibition	-	0.5426	54.26%
CYP2D6 inhibition	-	0.9415	94.15%
CYP1A2 inhibition	-	0.8039	80.39%
CYP2C8 inhibition	-	0.6987	69.87%
CYP inhibitory promiscuity	-	0.7759	77.59%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.8800	88.00%
Carcinogenicity (trinary)	Non-required	0.6308	63.08%
Eye corrosion	-	0.9820	98.20%
Eye irritation	-	0.8841	88.41%
Skin irritation	-	0.6085	60.85%
Skin corrosion	-	0.9804	98.04%
Ames mutagenesis	-	0.7854	78.54%
Human Ether-a-go-go-Related Gene inhibition	+	0.7819	78.19%
Micronuclear	-	0.9400	94.00%
Hepatotoxicity	-	0.6494	64.94%
skin sensitisation	+	0.7207	72.07%
Respiratory toxicity	+	0.5778	57.78%
Reproductive toxicity	+	0.6778	67.78%
Mitochondrial toxicity	+	0.6250	62.50%
Nephrotoxicity	+	0.5266	52.66%
Acute Oral Toxicity (c)	III	0.7493	74.93%
Estrogen receptor binding	-	0.5000	50.00%
Androgen receptor binding	+	0.5409	54.09%
Thyroid receptor binding	+	0.5473	54.73%
Glucocorticoid receptor binding	+	0.6434	64.34%
Aromatase binding	+	0.6461	64.61%
PPAR gamma	+	0.6072	60.72%
Honey bee toxicity	-	0.8980	89.80%
Biodegradation	-	0.5250	52.50%
Crustacea aquatic toxicity	-	0.7000	70.00%
Fish aquatic toxicity	+	1.0000	100.00%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	93.29%	91.11%
CHEMBL253	P34972	Cannabinoid CB2 receptor	90.95%	97.25%
CHEMBL340	P08684	Cytochrome P450 3A4	88.73%	91.19%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	87.99%	94.45%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	84.17%	95.56%
CHEMBL4246	P42680	Tyrosine-protein kinase TEC	83.56%	82.05%
CHEMBL221	P23219	Cyclooxygenase-1	82.18%	90.17%
CHEMBL2581	P07339	Cathepsin D	82.14%	98.95%
CHEMBL4227	P25090	Lipoxin A4 receptor	81.75%	100.00%
CHEMBL1994	P08235	Mineralocorticoid receptor	81.67%	100.00%
CHEMBL233	P35372	Mu opioid receptor	81.61%	97.93%
CHEMBL4187	Q99250	Sodium channel protein type II alpha subunit	81.38%	95.50%
CHEMBL5028	O14672	ADAM10	80.31%	97.50%

Plants that contains it

• Aglaia meridionalis
• Allium ursinum
• Ammi majus
• Arcangelisia gusanlung
• Artemisia schmidtiana
• Brickellia pendula
• Chloranthus spicatus
• Citrus deliciosa
• Cladanthus scariosus
• Cleidion brevipetiolatum
• Copaifera paupera
• Crotalaria spectabilis
• Cunninghamia lanceolata
• Endosamara racemosa
• Entandrophragma cylindricum
• Erucastrum gallicum
• Escallonia virgata
• Ficus maxima
• Gleichenia polypodioides
• Hesperocyparis nevadensis
• Jacobaea erratica
• Juniperus thurifera
• Lathyrus linifolius
• Leptospermum scoparium
• Magnolia acuminata
• Ocimum labiatum
• Onoclea struthiopteris
• Ophioglossum vulgatum
• Panax stipuleanatus
• Pinus densiflora
• Pinus nigra
• Plectranthus amboinicus
• Plumbago europaea
• Reissantia indica
• Rhodanthe stricta
• Simmondsia chinensis
• Tabebuia rosea
• Tanacetum santolina
• Timonius kaniensis

Cross-Links

• PubChem: 12303810
• NPASS: NPC3753
• LOTUS: LTS0202814
• wikiData: Q105347973