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Levopimaric acid

Family: Plantae - Pinaceae
Kingdom: Plantae
Class: Terpenoid
- Subclass: Abietane Diterpene

Canonical Smiles	CC(C1=CC[C@H]2C(=C1)CC[C@@H]1[C@]2(C)CCC[C@@]1(C)C(=O)O)C
InChI	InChI=1S/C20H30O2/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/h6,12-13,16-17H,5,7-11H2,1-4H3,(H,21,22)/t16-,17+,19+,20+/m0/s1
InChIKey	RWWVEQKPFPXLGL-ONCXSQPRSA-N
Formula	C₂₀H₃₀O₂
HBA	1
HBD	1
MW	302.46
Rotatable Bonds	2
TPSA	37.3
LogP	5.21
Number Rings	3
Number Aromatic Rings	0
Heavy Atom Count	22
Formal Charge	0
Fraction CSP3	0.75
Exact Mass	302.22
Number of Lipinski Rule Violations	1

#	Species	Family	Kingdom	NCBI Taxonomy ID
1	Cedrus atlantica	Pinaceae	Plantae	123597

Showing of synonyms

Barrero AF, Quílez del Moral JF, et al. (2005). Abietane diterpenes from the cones of Cedrus atlantica. Phytochemistry,2005,66(1),105-111. [View] [PubMed]

Pubchem: 221062

Cas: 79-54-9

Zinc: ZINC000003875511

Kegg Ligand: C11888

Chebi: 29615

Nmrshiftdb2: 60033477

Chembl: CHEMBL5401505

Comptox: DTXSID20878526

CPRiL: 415436

SMILES: C1C=CCC(C=12)C3C(CC2)CCCC3

Level: 0

Mol. Weight: 302.46 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp): -4.39
Human Oral Bioavailability 20%: Bioavailable
Human Intestinal Absorption: Absorbed
Madin-Darby Canine Kidney: -4.66
Human Oral Bioavailability 50%: Non-Bioavailable
P-Glycoprotein Inhibitor: Non-Inhibitor
P-Glycoprotein Substrate: Non-Substrate
Skin Permeability: -2.14

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Penetrable
Fraction Unbound (Human): 1.19
Plasma Protein Binding: 85.09
Steady State Volume of Distribution: -

Metabolism

Breast Cancer Resistance Protein: Inhibitor
CYP 1A2 Inhibitor: Non-Inhibitor
CYP 1A2 Substrate: Non-Substrate
CYP 2C19 Inhibitor: Non-Inhibitor
CYP 2C19 Substrate: Non-Substrate
CYP 2C9 Inhibitor: Inhibitor
CYP 2C9 Substrate: Substrate
CYP 2D6 Inhibitor: Non-Inhibitor
CYP 2D6 Substrate: Non-Substrate
CYP 3A4 Inhibitor: Non-Inhibitor
CYP 3A4 Substrate: Substrate
OATP1B1: Inhibitor
OATP1B3: Non-Inhibitor

Excretion

Clearance: 0.02
Organic Cation Transporter 2: Non-Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Safe
Avian: Safe
Bee: Toxic
Bioconcentration Factor: 0.54
Biodegradation: Safe
Carcinogenesis: Safe
Crustacean: Safe
Liver Injury I (DILI): Safe
Eye Corrosion: Safe
Eye Irritation: Toxic
Maximum Tolerated Dose: 0.56
Liver Injury II: Toxic
hERG Blockers: Safe
Daphnia Maga: 2.56
Micronucleos: Safe
NR-AhR: Toxic
NR-AR: Safe
NR-AR-LBD: Safe
NR-Aromatase: Safe
NR-ER: Safe
NR-ER-LBD: Safe
NR-GR: Safe
NR-PPAR-gamma: Safe
NR-TR: Safe
T. Pyriformis: -0.13
Rat (Acute): 2.18
Rat (Chronic Oral): 1.5
Fathead Minnow: 3.83
Respiratory Disease: Toxic
Skin Sensitisation: Toxic
SR-ARE: Toxic
SR-ATAD5: Safe
SR-HSE: Safe
SR-MMP: Safe
SR-p53: Safe

General Properties

Boiling Point: 353.2
Hydration Free Energy: -4.62
Log(D) at pH=7.4: 2.57
Log(P): 5.32
Log S: -5.2
Log(Vapor Pressure): -6.54
Melting Point: 170.36
pKa Acid: 6.09
pKa Basic: 7.53

Protein Name	UniProt ID	Entry Name	Species	#Pharmacophore Points	Probability (0.7 ≤ Tversky Score ≤ 1.0)
Deacetoxycephalosporin C synthase	P18548	CEFE_STRCL	Streptomyces clavuligerus	3	0.9088
Deacetoxycephalosporin C synthase	P18548	CEFE_STRCL	Streptomyces clavuligerus	3	0.9088
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	3	0.8460
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	3	0.8460
Mycinamicin III 3''-O-methyltransferase	Q49492	MYCF_MICGR	Micromonospora griseorubida	2	0.8429
Mycinamicin III 3''-O-methyltransferase	Q49492	MYCF_MICGR	Micromonospora griseorubida	2	0.8429
Lactoylglutathione lyase	Q9CPU0	LGUL_MOUSE	Mus musculus	3	0.8177
Lactoylglutathione lyase	Q9CPU0	LGUL_MOUSE	Mus musculus	3	0.8177
Retinol-binding protein 1	P02696	RET1_RAT	Rattus norvegicus	3	0.8029
Retinol-binding protein 1	P02696	RET1_RAT	Rattus norvegicus	3	0.8029
Vitamin D3 receptor	P13053	VDR_RAT	Rattus norvegicus	4	0.8009
Vitamin D3 receptor	P13053	VDR_RAT	Rattus norvegicus	4	0.8009
Retinol dehydratase	Q26490	Q26490_SPOFR	Spodoptera frugiperda	3	0.7906
Retinol dehydratase	Q26490	Q26490_SPOFR	Spodoptera frugiperda	3	0.7906
Aldo-keto reductase family 1 member C1	Q04828	AK1C1_HUMAN	Homo sapiens	3	0.7829
Aldo-keto reductase family 1 member C1	Q04828	AK1C1_HUMAN	Homo sapiens	3	0.7829
Ferrochelatase, mitochondrial	P22830	HEMH_HUMAN	Homo sapiens	3	0.7696
Ferrochelatase, mitochondrial	P22830	HEMH_HUMAN	Homo sapiens	3	0.7696
Retinol-binding protein 1	P02696	RET1_RAT	Rattus norvegicus	3	0.7565
Retinol-binding protein 1	P02696	RET1_RAT	Rattus norvegicus	3	0.7565
Prostaglandin reductase 2	Q8N8N7	PTGR2_HUMAN	Homo sapiens	3	0.7159
Prostaglandin reductase 2	Q8N8N7	PTGR2_HUMAN	Homo sapiens	3	0.7159
Retinaldehyde-binding protein 1	P12271	RLBP1_HUMAN	Homo sapiens	4	0.7139
Retinaldehyde-binding protein 1	P12271	RLBP1_HUMAN	Homo sapiens	4	0.7139
Thyroid hormone receptor alpha	P04625	THA_CHICK	Gallus gallus	3	0.7100
Thyroid hormone receptor alpha	P04625	THA_CHICK	Gallus gallus	3	0.7100
Ferrochelatase, mitochondrial	P22830	HEMH_HUMAN	Homo sapiens	3	0.7062
Ferrochelatase, mitochondrial	P22830	HEMH_HUMAN	Homo sapiens	3	0.7062
Vitamin D3 receptor	P13053	VDR_RAT	Rattus norvegicus	4	0.7027
Vitamin D3 receptor	P13053	VDR_RAT	Rattus norvegicus	4	0.7027

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