Costic acid

Details

• Internal ID: 24d5529f-925e-456e-8191-ac238300ac00
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Sesquiterpenoids > Eudesmane, isoeudesmane or cycloeudesmane sesquiterpenoids
• IUPAC Name: 2-[(2R,4aR,8aS)-4a-methyl-8-methylidene-1,2,3,4,5,6,7,8a-octahydronaphthalen-2-yl]prop-2-enoic acid
• SMILES (Canonical): CC12CCCC(=C)C1CC(CC2)C(=C)C(=O)O
• SMILES (Isomeric): C[C@]12CCCC(=C)[C@@H]1C[C@@H](CC2)C(=C)C(=O)O
• InChI: InChI=1S/C15H22O2/c1-10-5-4-7-15(3)8-6-12(9-13(10)15)11(2)14(16)17/h12-13H,1-2,4-9H2,3H3,(H,16,17)/t12-,13+,15-/m1/s1
• InChI Key: UJQGVDNQDFTTLZ-VNHYZAJKSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₁₅H₂₂O₂
• Molecular Weight: 234.33 g/mol
• Exact Mass: 234.161979940 g/mol
• Topological Polar Surface Area (TPSA): 37.30 Ų
• XlogP: 4.10
• Atomic LogP (AlogP): 3.79
• H-Bond Acceptor: 1
• H-Bond Donor: 1
• Rotatable Bonds: 2

Synonyms

• 3650-43-9
• beta-Costic acid
• Costus acid
• Cosstic acid
• UNII-6109CN8DDD
• 6109CN8DDD
• Eudesma-4(14),11(13)-dien-12-oic acid
• 2-Naphthaleneacetic acid, decahydro-4a-methyl-alpha,8-bis(methylene)-, (2R-(2alpha,4aalpha,8abeta))-
• Costic acid; Costus acid
• beta-Costicacid
• -Costic acid
• 2-NAPHTHALENEACETIC ACID, DECAHYDRO-4A-METHYL-.ALPHA.,8-BIS(METHYLENE)-, (2R-(2.ALPHA.,4A.ALPHA.,8A.BETA.))-
• 2-Naphthaleneacetic acid, decahydro-4a-methyl-.alpha.,8-bis(methylene)-, [2R-(2.alpha.,4a.alpha.,8a.beta.)]-
• .BETA.-COSTIC ACID
• 2-[(2R,4aR,8aS)-4a-methyl-8-methylidene-1,2,3,4,5,6,7,8a-octahydronaphthalen-2-yl]prop-2-enoic acid
• CHEMBL486398
• DTXSID50190001
• AKOS032948521
• A874339
• Q27263263
• (2R,4aR,8aS)-Decahydro-4a-methyl-alpha,8-bis(methylene)-2-naphthaleneacetic acid
• 2-NAPHTHALENEACETIC ACID, 1,2.BETA.,3,4,4A,5,6,7,8,8A.BETA.-DECAHYDRO-4A.ALPHA.-METHYL-.ALPHA.,8-DIMETHYLENE-
• 2-NAPHTHALENEACETIC ACID, 1,2beta,3,4,4A,5,6,7,8,8Abeta-DECAHYDRO-4Aalpha-METHYL-alpha,8-DIMETHYLENE-
• 2-NAPHTHALENEACETIC ACID, DECAHYDRO-4A-METHYL-.ALPHA.,8-BIS(METHYLENE)-, (2R,4AR,8AS)-
• 2-NAPHTHALENEACETIC ACID, DECAHYDRO-4A-METHYL-alpha,8-BIS(METHYLENE)-, (2R,4AR,8AS)-

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9950	99.50%
Caco-2	+	0.7249	72.49%
Blood Brain Barrier	+	0.7250	72.50%
Human oral bioavailability	+	0.6286	62.86%
Subcellular localzation	Plasma membrane	0.4759	47.59%
OATP2B1 inhibitior	-	0.8506	85.06%
OATP1B1 inhibitior	+	0.9038	90.38%
OATP1B3 inhibitior	-	0.2148	21.48%
MATE1 inhibitior	-	0.9200	92.00%
OCT2 inhibitior	+	0.6500	65.00%
BSEP inhibitior	-	0.8915	89.15%
P-glycoprotein inhibitior	-	0.9316	93.16%
P-glycoprotein substrate	-	0.8912	89.12%
CYP3A4 substrate	+	0.5496	54.96%
CYP2C9 substrate	-	0.6131	61.31%
CYP2D6 substrate	-	0.8970	89.70%
CYP3A4 inhibition	-	0.8231	82.31%
CYP2C9 inhibition	-	0.6758	67.58%
CYP2C19 inhibition	-	0.5000	50.00%
CYP2D6 inhibition	-	0.9229	92.29%
CYP1A2 inhibition	-	0.6574	65.74%
CYP2C8 inhibition	-	0.7892	78.92%
CYP inhibitory promiscuity	-	0.8993	89.93%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.8900	89.00%
Carcinogenicity (trinary)	Non-required	0.5709	57.09%
Eye corrosion	-	0.9301	93.01%
Eye irritation	+	0.5728	57.28%
Skin irritation	-	0.5530	55.30%
Skin corrosion	-	0.9649	96.49%
Ames mutagenesis	-	0.6537	65.37%
Human Ether-a-go-go-Related Gene inhibition	-	0.5000	50.00%
Micronuclear	-	0.8900	89.00%
Hepatotoxicity	+	0.5553	55.53%
skin sensitisation	+	0.7331	73.31%
Respiratory toxicity	-	0.6222	62.22%
Reproductive toxicity	+	0.5596	55.96%
Mitochondrial toxicity	+	0.5500	55.00%
Nephrotoxicity	-	0.6684	66.84%
Acute Oral Toxicity (c)	III	0.8523	85.23%
Estrogen receptor binding	-	0.5092	50.92%
Androgen receptor binding	-	0.5000	50.00%
Thyroid receptor binding	-	0.6073	60.73%
Glucocorticoid receptor binding	+	0.6539	65.39%
Aromatase binding	-	0.6269	62.69%
PPAR gamma	+	0.5354	53.54%
Honey bee toxicity	-	0.9272	92.72%
Biodegradation	-	0.6000	60.00%
Crustacea aquatic toxicity	-	0.5700	57.00%
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
CHEMBL253	P34972	Cannabinoid CB2 receptor	96.21%	97.25%
CHEMBL221	P23219	Cyclooxygenase-1	91.00%	90.17%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	90.28%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	89.20%	91.11%
CHEMBL3137262	O60341	LSD1/CoREST complex	88.87%	97.09%
CHEMBL340	P08684	Cytochrome P450 3A4	85.30%	91.19%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	84.58%	95.56%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	82.40%	99.23%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	81.76%	95.50%
CHEMBL1994	P08235	Mineralocorticoid receptor	80.11%	100.00%

Plants that contains it

• Ambrosia artemisioides
• Ambrosia ilicifolia
• Apalochlamys spectabilis
• Arctium lappa
• Artemisia phaeolepis
• Chiliadenus montanus
• Cratystylis microphylla
• Cronquistianthus bishopii
• Dimerostemma lippioides
• Dittrichia graveolens
• Dolomiaea souliei
• Echinops ritro
• Eupatorium capillifolium
• Ficus mucuso
• Fitchia speciosa
• Heracleum maximum
• Heterocoma ekmaniana
• Klasea latifolia
• Laggera alata
• Laggera crispata
• Machilus wangchiana
• Marshallia obovata
• Ophryosporus floribundus
• Schisandra sphenanthera
• Schistostephium crataegifolium
• Stevia chamaedrys
• Stevia polyphylla

Cross-Links

• PubChem: 6451579
• NPASS: NPC235586
• LOTUS: LTS0263923
• wikiData: Q27263263