4-epi-abietic acid - Compound Card

4-epi-abietic acid

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4-epi-abietic acid

Structure
Zoomed Structure
  • Family: Plantae - Cupressaceae
  • Kingdom: Plantae
  • Class: Terpenoid
    • Subclass: Diterpenoid
Canonical Smiles CC(C1=CC2=CCC3[C@]([C@H]2CC1)(C)CCC[C@]3(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/h7,12-13,16-17H,5-6,8-11H2,1-4H3,(H,21,22)/t16-,17?,19+,20-/m0/s1
InChIKey RSWGJHLUYNHPMX-NGWLPYQTSA-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 Juniperus species Cupressaceae Plantae 13100

Showing of synonyms

  • Barrero AF, Quılez del Moral JF, et al. (2004). Oxygenated diterpenes and other constituents from Moroccan Juniperus phoenicea and Juniperus thurifera var. africana. Phytochemistry,2004,65,2507-2515. [View] [PubMed]
Pubchem: 44135363

No compound-protein relationship available.

Structure

SMILES: C1=CCCC(C1=2)C3C(CC2)CCCC3

Level: 0

Mol. Weight: 302.46 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.44
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.58
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.16

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.97
Plasma Protein Binding
78.75
Steady State Volume of Distribution
-

Metabolism

Breast Cancer Resistance Protein
Non-Inhibitor
CYP 1A2 Inhibitor
Non-Inhibitor
CYP 1A2 Substrate
Non-Substrate
CYP 2C19 Inhibitor
Inhibitor
CYP 2C19 Substrate
Non-Substrate
CYP 2C9 Inhibitor
Non-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
1.71
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
0.59
Biodegradation
Safe
Carcinogenesis
Toxic
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Toxic
Maximum Tolerated Dose
0.9
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
2.64
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
0.29
Rat (Acute)
2.09
Rat (Chronic Oral)
1.79
Fathead Minnow
3.92
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
355.8
Hydration Free Energy
-4.9
Log(D) at pH=7.4
2.71
Log(P)
5.68
Log S
-4.82
Log(Vapor Pressure)
-6.28
Melting Point
160.12
pKa Acid
6.29
pKa Basic
7.94
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 3 0.8914
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 3 0.8914
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.8386
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.8386
Vitamin D3 receptor P13053 VDR_RAT Rattus norvegicus 4 0.8363
Vitamin D3 receptor P13053 VDR_RAT Rattus norvegicus 4 0.8363
Retinol-binding protein 1 P02696 RET1_RAT Rattus norvegicus 3 0.8082
Retinol-binding protein 1 P02696 RET1_RAT Rattus norvegicus 3 0.8082
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.7983
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.7983
Beta-1 adrenergic receptor P07700 ADRB1_MELGA Meleagris gallopavo 3 0.7886
Beta-1 adrenergic receptor P07700 ADRB1_MELGA Meleagris gallopavo 3 0.7886
Sex hormone-binding globulin P04278 SHBG_HUMAN Homo sapiens 3 0.7833
Sex hormone-binding globulin P04278 SHBG_HUMAN Homo sapiens 3 0.7833
Abscisic acid receptor PYL3 Q9SSM7 PYL3_ARATH Arabidopsis thaliana 3 0.7767
Abscisic acid receptor PYL3 Q9SSM7 PYL3_ARATH Arabidopsis thaliana 3 0.7767
Acetylcholinesterase P04058 ACES_TETCF Tetronarce californica 3 0.7736
Acetylcholinesterase P04058 ACES_TETCF Tetronarce californica 3 0.7736
Beta-lactoglobulin P02754 LACB_BOVIN Bos taurus 3 0.7729
Beta-lactoglobulin P02754 LACB_BOVIN Bos taurus 3 0.7729
Retinaldehyde-binding protein 1 P12271 RLBP1_HUMAN Homo sapiens 4 0.7712
Retinaldehyde-binding protein 1 P12271 RLBP1_HUMAN Homo sapiens 4 0.7712
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 3 0.7699
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 3 0.7699
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7697
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7697
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.7667
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.7667
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.7646
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.7646
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7592
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7592
Cellular retinoic acid-binding protein 2 P29373 RABP2_HUMAN Homo sapiens 3 0.7591
Cellular retinoic acid-binding protein 2 P29373 RABP2_HUMAN Homo sapiens 3 0.7591
Fatty acid-binding protein, liver P80226 FABPL_CHICK Gallus gallus 3 0.7448
Fatty acid-binding protein, liver P80226 FABPL_CHICK Gallus gallus 3 0.7448
Multidrug transporter MdfA P0AEY8 MDFA_ECOLI Escherichia coli 3 0.7381
Multidrug transporter MdfA P0AEY8 MDFA_ECOLI Escherichia coli 3 0.7381
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7377
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7377
Probable NDP-rhamnosyltransferase Q9ALM8 Q9ALM8_SACSN Saccharopolyspora spinosa 3 0.7296
Probable NDP-rhamnosyltransferase Q9ALM8 Q9ALM8_SACSN Saccharopolyspora spinosa 3 0.7296
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.7295
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.7295
Beta-elicitin cryptogein P15570 ELIB_PHYCR Phytophthora cryptogea 3 0.7289
Beta-elicitin cryptogein P15570 ELIB_PHYCR Phytophthora cryptogea 3 0.7289
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7233
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7233
Retinol dehydratase Q26490 Q26490_SPOFR Spodoptera frugiperda 3 0.7190
Retinol dehydratase Q26490 Q26490_SPOFR Spodoptera frugiperda 3 0.7190
Vitamin D3 receptor P13053 VDR_RAT Rattus norvegicus 3 0.7126
Vitamin D3 receptor P13053 VDR_RAT Rattus norvegicus 3 0.7126
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7097
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7097
Vitamin D3 receptor P13053 VDR_RAT Rattus norvegicus 4 0.7096
Vitamin D3 receptor P13053 VDR_RAT Rattus norvegicus 4 0.7096

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