Hardwickiic acid

Details

• Internal ID: 8c85ca7e-b32e-4f91-a706-9810b37359ad
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Diterpenoids > Colensane and clerodane diterpenoids
• IUPAC Name: (4aR,5S,6R,8aR)-5-[2-(furan-3-yl)ethyl]-5,6,8a-trimethyl-3,4,4a,6,7,8-hexahydronaphthalene-1-carboxylic acid
• SMILES (Canonical): CC1CCC2(C(C1(C)CCC3=COC=C3)CCC=C2C(=O)O)C
• SMILES (Isomeric): C[C@@H]1CC[C@@]2([C@@H]([C@@]1(C)CCC3=COC=C3)CCC=C2C(=O)O)C
• InChI: InChI=1S/C20H28O3/c1-14-7-10-20(3)16(18(21)22)5-4-6-17(20)19(14,2)11-8-15-9-12-23-13-15/h5,9,12-14,17H,4,6-8,10-11H2,1-3H3,(H,21,22)/t14-,17-,19+,20+/m1/s1
• InChI Key: HHWOKJDCJVESIF-JBCDFXQESA-N
• Popularity: 14 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₀H₂₈O₃
• Molecular Weight: 316.40 g/mol
• Exact Mass: 316.20384475 g/mol
• Topological Polar Surface Area (TPSA): 50.40 Ų
• XlogP: 5.60
• Atomic LogP (AlogP): 5.08
• H-Bond Acceptor: 2
• H-Bond Donor: 1
• Rotatable Bonds: 4

Synonyms

• (-)-Hardwickiic acid
• 1782-65-6
• (-)-Hardwickic Acid
• (?)-Hardwickiic acid
• (5R,8R,9S,10R)-(-)-Hardwikiic acid; Hardwickiic acid, (-)-
• CHEMBL461615
• MEGxp0_001619
• ACon1_001998
• AKOS040761815
• NCGC00179931-01
• MS-24669
• BRD-K78473285-001-01-5
• (4~{a}~{R},5~{S},6~{R},8~{a}~{R})-5-[2-(furan-3-yl)ethyl]-5,6,8~{a}-trimethyl-3,4,4~{a},6,7,8-hexahydronaphthalene-1-carboxylic acid
• (4AR,5S,6R,8AR)-5-[2-(FURAN-3-YL)ETHYL]-5,6,8A-TRIMETHYL-3,4,4A,6,7,8-HEXAHYDRONAPHTHALENE-1-CARBOXYLIC ACID
• UK0

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9940	99.40%
Caco-2	+	0.8421	84.21%
Blood Brain Barrier	+	0.7250	72.50%
Human oral bioavailability	-	0.5571	55.71%
Subcellular localzation	Plasma membrane	0.5247	52.47%
OATP2B1 inhibitior	-	0.8633	86.33%
OATP1B1 inhibitior	+	0.7405	74.05%
OATP1B3 inhibitior	+	0.8723	87.23%
MATE1 inhibitior	-	0.8800	88.00%
OCT2 inhibitior	-	0.5750	57.50%
BSEP inhibitior	-	0.5149	51.49%
P-glycoprotein inhibitior	-	0.7621	76.21%
P-glycoprotein substrate	-	0.7915	79.15%
CYP3A4 substrate	+	0.5889	58.89%
CYP2C9 substrate	+	0.5821	58.21%
CYP2D6 substrate	-	0.9051	90.51%
CYP3A4 inhibition	+	0.5299	52.99%
CYP2C9 inhibition	-	0.6753	67.53%
CYP2C19 inhibition	-	0.5273	52.73%
CYP2D6 inhibition	-	0.8963	89.63%
CYP1A2 inhibition	+	0.5607	56.07%
CYP2C8 inhibition	+	0.5242	52.42%
CYP inhibitory promiscuity	+	0.5466	54.66%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.8600	86.00%
Carcinogenicity (trinary)	Non-required	0.5769	57.69%
Eye corrosion	-	0.9905	99.05%
Eye irritation	-	0.9636	96.36%
Skin irritation	-	0.5995	59.95%
Skin corrosion	-	0.9596	95.96%
Ames mutagenesis	-	0.7570	75.70%
Human Ether-a-go-go-Related Gene inhibition	+	0.7757	77.57%
Micronuclear	-	0.8200	82.00%
Hepatotoxicity	-	0.5848	58.48%
skin sensitisation	-	0.6149	61.49%
Respiratory toxicity	+	0.5444	54.44%
Reproductive toxicity	+	0.6444	64.44%
Mitochondrial toxicity	+	0.7125	71.25%
Nephrotoxicity	-	0.5644	56.44%
Acute Oral Toxicity (c)	III	0.6341	63.41%
Estrogen receptor binding	+	0.8169	81.69%
Androgen receptor binding	+	0.5676	56.76%
Thyroid receptor binding	+	0.6220	62.20%
Glucocorticoid receptor binding	+	0.6381	63.81%
Aromatase binding	+	0.7916	79.16%
PPAR gamma	+	0.6002	60.02%
Honey bee toxicity	-	0.8988	89.88%
Biodegradation	-	0.8750	87.50%
Crustacea aquatic toxicity	-	0.6600	66.00%
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
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	95.14%	96.09%
CHEMBL253	P34972	Cannabinoid CB2 receptor	95.06%	97.25%
CHEMBL2581	P07339	Cathepsin D	93.29%	98.95%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	91.92%	91.11%
CHEMBL3807	P17706	T-cell protein-tyrosine phosphatase	91.32%	93.00%
CHEMBL3137262	O60341	LSD1/CoREST complex	89.90%	97.09%
CHEMBL4040	P28482	MAP kinase ERK2	85.87%	83.82%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	85.23%	94.45%
CHEMBL1293249	Q13887	Kruppel-like factor 5	83.92%	86.33%
CHEMBL221	P23219	Cyclooxygenase-1	82.21%	90.17%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	81.18%	95.56%

Plants that contains it

• Baccharis macraei
• Baccharis tola subsp. tola
• Chromolaena pulchella
• Chrozophora oblongifolia
• Copaifera duckei
• Croton aromaticus
• Croton californicus
• Croton lechleri
• Croton megistocarpus
• Croton sonderianus
• Diplostephium meyenii
• Grangea maderaspatana
• Ipomoea nil
• Laennecia coulteri
• Microglossa pyrifolia
• Pulicaria salviifolia
• Salvia divinorum
• Salvia regla
• Salvia wagneriana
• Solidago rugosa

Cross-Links

• PubChem: 15559629
• NPASS: NPC207294
• LOTUS: LTS0196249
• wikiData: Q104254227