Pinifolic Acid

Details

• Internal ID: 19af29c1-997c-4389-845b-ace7cd971ff7
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Diterpenoids
• IUPAC Name: (1R,4aR,5S,8aR)-5-[(3S)-4-carboxy-3-methylbutyl]-1,4a-dimethyl-6-methylidene-3,4,5,7,8,8a-hexahydro-2H-naphthalene-1-carboxylic acid
• SMILES (Canonical): CC(CCC1C(=C)CCC2C1(CCCC2(C)C(=O)O)C)CC(=O)O
• SMILES (Isomeric): C[C@@H](CC[C@H]1C(=C)CC[C@@H]2[C@@]1(CCC[C@@]2(C)C(=O)O)C)CC(=O)O
• InChI: InChI=1S/C20H32O4/c1-13(12-17(21)22)6-8-15-14(2)7-9-16-19(15,3)10-5-11-20(16,4)18(23)24/h13,15-16H,2,5-12H2,1,3-4H3,(H,21,22)(H,23,24)/t13-,15-,16+,19+,20+/m0/s1
• InChI Key: HPQKNJHVWUWAOR-QBSBYYDBSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₂₀H₃₂O₄
• Molecular Weight: 336.50 g/mol
• Exact Mass: 336.23005950 g/mol
• Topological Polar Surface Area (TPSA): 74.60 Ų
• XlogP: 4.70
• Atomic LogP (AlogP): 4.74
• H-Bond Acceptor: 2
• H-Bond Donor: 2
• Rotatable Bonds: 6

Synonyms

• 1412-99-3
• (1R,4aR,5S,8aR)-5-[(3S)-4-carboxy-3-methylbutyl]-1,4a-dimethyl-6-methylidene-3,4,5,7,8,8a-hexahydro-2H-naphthalene-1-carboxylic acid
• CHEMBL2048915
• XP170490
• Pinifolic acid - Pinus sylvestris (Scots pine)

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9798	97.98%
Caco-2	+	0.6434	64.34%
Blood Brain Barrier	+	0.6000	60.00%
Human oral bioavailability	-	0.5714	57.14%
Subcellular localzation	Mitochondria	0.7206	72.06%
OATP2B1 inhibitior	-	0.8634	86.34%
OATP1B1 inhibitior	+	0.8382	83.82%
OATP1B3 inhibitior	-	0.2411	24.11%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.6521	65.21%
BSEP inhibitior	+	0.5939	59.39%
P-glycoprotein inhibitior	-	0.7537	75.37%
P-glycoprotein substrate	-	0.7328	73.28%
CYP3A4 substrate	+	0.6046	60.46%
CYP2C9 substrate	-	0.5859	58.59%
CYP2D6 substrate	-	0.8733	87.33%
CYP3A4 inhibition	-	0.6135	61.35%
CYP2C9 inhibition	-	0.9265	92.65%
CYP2C19 inhibition	-	0.9317	93.17%
CYP2D6 inhibition	-	0.9508	95.08%
CYP1A2 inhibition	-	0.8934	89.34%
CYP2C8 inhibition	-	0.8449	84.49%
CYP inhibitory promiscuity	-	0.9165	91.65%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.9100	91.00%
Carcinogenicity (trinary)	Non-required	0.7190	71.90%
Eye corrosion	-	0.9882	98.82%
Eye irritation	-	0.7287	72.87%
Skin irritation	-	0.5470	54.70%
Skin corrosion	-	0.9676	96.76%
Ames mutagenesis	-	0.7900	79.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4818	48.18%
Micronuclear	-	0.8200	82.00%
Hepatotoxicity	-	0.5766	57.66%
skin sensitisation	+	0.6397	63.97%
Respiratory toxicity	+	0.5444	54.44%
Reproductive toxicity	+	0.7444	74.44%
Mitochondrial toxicity	+	0.7500	75.00%
Nephrotoxicity	-	0.5680	56.80%
Acute Oral Toxicity (c)	III	0.7339	73.39%
Estrogen receptor binding	+	0.6507	65.07%
Androgen receptor binding	+	0.5853	58.53%
Thyroid receptor binding	+	0.6666	66.66%
Glucocorticoid receptor binding	+	0.7450	74.50%
Aromatase binding	-	0.5150	51.50%
PPAR gamma	-	0.5834	58.34%
Honey bee toxicity	-	0.9017	90.17%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	-	0.7200	72.00%
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
CHEMBL221	P23219	Cyclooxygenase-1	94.50%	90.17%
CHEMBL253	P34972	Cannabinoid CB2 receptor	94.31%	97.25%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	93.78%	94.45%
CHEMBL4685	P14902	Indoleamine 2,3-dioxygenase	90.65%	96.38%
CHEMBL2581	P07339	Cathepsin D	89.27%	98.95%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	88.61%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	87.70%	96.09%
CHEMBL1907598	P05106	Integrin alpha-V/beta-3	86.06%	95.71%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	84.30%	90.71%
CHEMBL4227	P25090	Lipoxin A4 receptor	83.06%	100.00%
CHEMBL3130	O00329	PI3-kinase p110-delta subunit	82.62%	96.47%
CHEMBL340	P08684	Cytochrome P450 3A4	82.55%	91.19%
CHEMBL1994	P08235	Mineralocorticoid receptor	80.23%	100.00%

Plants that contains it

• Alcea rosea
• Alpinia roxburghii
• Balanops australiana
• Davallia perdurans
• Euonymus tingens
• Euphorbia cornigera
• Gonzalezia decurrens
• Hylocomium splendens
• Kokoona reflexa
• Maesa ramentacea
• Millettia laurentii
• Monodora tenuifolia
• Ocimum tenuiflorum
• Pinus nigra
• Pinus strobus
• Pinus sylvestris
• Pluchea odorata
• Salacia lehmbachii
• Salvia yosgadensis
• Sideritis brevibracteata
• Sideroxylon cubense

Cross-Links

• PubChem: 12314311
• NPASS: NPC36616
• ChEMBL: CHEMBL2048915
• LOTUS: LTS0084876
• wikiData: Q104253487