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Lambertiamic acid

Family: Plantae - Leguminosae/Fabaceae
Kingdom: Plantae
Class: Terpenoid

Canonical Smiles	C=C1CC[C@@H]2[C@]([C@H]1CCc1cocc1)(C)CCC[C@]2(C)C(=O)O
InChI	InChI=1S/C20H28O3/c1-14-5-8-17-19(2,10-4-11-20(17,3)18(21)22)16(14)7-6-15-9-12-23-13-15/h9,12-13,16-17H,1,4-8,10-11H2,2-3H3,(H,21,22)/t16-,17+,19+,20-/m0/s1
InChIKey	ZQHJXKYYELWEOK-CUDHKJQZSA-N
Formula	C₂₀H₂₈O₃
HBA	2
HBD	1
MW	316.44
Rotatable Bonds	4
TPSA	50.44
LogP	5.08
Number Rings	3
Number Aromatic Rings	1
Heavy Atom Count	23
Formal Charge	0
Fraction CSP3	0.65
Exact Mass	316.2
Number of Lipinski Rule Violations	1

#	Species	Family	Kingdom	NCBI Taxonomy ID
1	Piliostigma thonningii	Leguminosae/Fabaceae	Plantae	653098

Showing of synonyms

Snatzke F, Wolff P. (1989). Constituents of the roots of Pillostigma Thonningh (lhguminosah).. Bulletin of the Chemical Society of Ethiopia,1989,3(2),135-138. [View] [PubMed]

Pubchem: 11869599

Cas: 4966-13-6

Zinc: ZINC000003881834

Nmrshiftdb2: 60067581

Chembl: CHEMBL463690

CPRiL: 71270

SMILES: C1CCCC(C12)CCC(=C)C2CCc3ccoc3

Level: 1

Mol. Weight: 316.44 g/mol

SMILES: C=C(C1)CCC(C12)CCCC2

Level: 0

Mol. Weight: 316.44 g/mol

SMILES: c1ccoc1

Level: 0

Mol. Weight: 316.44 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp): -4.48
Human Oral Bioavailability 20%: Bioavailable
Human Intestinal Absorption: Absorbed
Madin-Darby Canine Kidney: -4.69
Human Oral Bioavailability 50%: Non-Bioavailable
P-Glycoprotein Inhibitor: Inhibitor
P-Glycoprotein Substrate: Non-Substrate
Skin Permeability: -2.3

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Penetrable
Fraction Unbound (Human): 1.23
Plasma Protein Binding: 88.85
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: 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: 0.73
Organic Cation Transporter 2: Non-Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Safe
Avian: Safe
Bee: Toxic
Bioconcentration Factor: 0.39
Biodegradation: Safe
Carcinogenesis: Toxic
Crustacean: Safe
Liver Injury I (DILI): Safe
Eye Corrosion: Safe
Eye Irritation: Safe
Maximum Tolerated Dose: -0.24
Liver Injury II: Toxic
hERG Blockers: Safe
Daphnia Maga: 2.66
Micronucleos: Safe
NR-AhR: Safe
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: -0.94
Rat (Acute): 3.27
Rat (Chronic Oral): 2.11
Fathead Minnow: 3.96
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: 363.48
Hydration Free Energy: -5.35
Log(D) at pH=7.4: 2.24
Log(P): 4.84
Log S: -4.97
Log(Vapor Pressure): -8.02
Melting Point: 139.16
pKa Acid: 5.57
pKa Basic: 7.52

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	0.9908
Photosynthetic reaction center cytochrome c subunit	P07173	CYCR_BLAVI	Blastochloris viridis	3	0.9908
Probable NDP-rhamnosyltransferase	Q9ALM8	Q9ALM8_SACSN	Saccharopolyspora spinosa	3	0.9545
Probable NDP-rhamnosyltransferase	Q9ALM8	Q9ALM8_SACSN	Saccharopolyspora spinosa	3	0.9545
ABC-type polar amino acid transport system, ATPase component	Q8RCC2	Q8RCC2_CALS4	Caldanaerobacter subterraneus subsp. tengcongensis	3	0.9114
ABC-type polar amino acid transport system, ATPase component	Q8RCC2	Q8RCC2_CALS4	Caldanaerobacter subterraneus subsp. tengcongensis	3	0.9114
Lactoylglutathione lyase	Q9CPU0	LGUL_MOUSE	Mus musculus	3	0.9019
Lactoylglutathione lyase	Q9CPU0	LGUL_MOUSE	Mus musculus	3	0.9019
Soluble acetylcholine receptor	Q8WSF8	Q8WSF8_APLCA	Aplysia californica	3	0.8786
Soluble acetylcholine receptor	Q8WSF8	Q8WSF8_APLCA	Aplysia californica	3	0.8786
Protein LlR18A	P52778	L18A_LUPLU	Lupinus luteus	3	0.8749
Protein LlR18A	P52778	L18A_LUPLU	Lupinus luteus	3	0.8749
Steroid Delta-isomerase	P07445	SDIS_PSEPU	Pseudomonas putida	2	0.8429
Steroid Delta-isomerase	P07445	SDIS_PSEPU	Pseudomonas putida	2	0.8429
Cellular retinoic acid-binding protein 2	P29373	RABP2_HUMAN	Homo sapiens	3	0.8373
Cellular retinoic acid-binding protein 2	P29373	RABP2_HUMAN	Homo sapiens	3	0.8373
Branched-chain-amino-acid aminotransferase, mitochondrial	O15382	BCAT2_HUMAN	Homo sapiens	3	0.8005
Branched-chain-amino-acid aminotransferase, mitochondrial	O15382	BCAT2_HUMAN	Homo sapiens	3	0.8005
Abscisic acid receptor PYR1	O49686	PYR1_ARATH	Arabidopsis thaliana	3	0.7999
Abscisic acid receptor PYR1	O49686	PYR1_ARATH	Arabidopsis thaliana	3	0.7999
Beta-1 adrenergic receptor	P07700	ADRB1_MELGA	Meleagris gallopavo	3	0.7927
Beta-1 adrenergic receptor	P07700	ADRB1_MELGA	Meleagris gallopavo	3	0.7927
Ferrochelatase, mitochondrial	P22830	HEMH_HUMAN	Homo sapiens	3	0.7901
Ferrochelatase, mitochondrial	P22830	HEMH_HUMAN	Homo sapiens	3	0.7901
Aldo-keto reductase family 1 member C3	P42330	AK1C3_HUMAN	Homo sapiens	3	0.7889
Aldo-keto reductase family 1 member C3	P42330	AK1C3_HUMAN	Homo sapiens	3	0.7889
Aldo-keto reductase family 1 member C2	P52895	AK1C2_HUMAN	Homo sapiens	3	0.7873
Aldo-keto reductase family 1 member C2	P52895	AK1C2_HUMAN	Homo sapiens	3	0.7873
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	2	0.7837
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	2	0.7837
Progesterone receptor	P06401	PRGR_HUMAN	Homo sapiens	2	0.7797
Progesterone receptor	P06401	PRGR_HUMAN	Homo sapiens	2	0.7797
Aldo-keto reductase family 1 member C3	P42330	AK1C3_HUMAN	Homo sapiens	2	0.7790
Aldo-keto reductase family 1 member C3	P42330	AK1C3_HUMAN	Homo sapiens	2	0.7790
Aldo-keto reductase family 1 member C2	P52895	AK1C2_HUMAN	Homo sapiens	2	0.7772
Aldo-keto reductase family 1 member C2	P52895	AK1C2_HUMAN	Homo sapiens	2	0.7772
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	2	0.7756
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	2	0.7756
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	2	0.7721
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	2	0.7721
3-ketosteroid dehydrogenase	Q9RA02	Q9RA02_RHOER	Rhodococcus erythropolis	2	0.7718
3-ketosteroid dehydrogenase	Q9RA02	Q9RA02_RHOER	Rhodococcus erythropolis	2	0.7718
ActVA 6 protein	Q53908	Q53908_STRCH	Streptomyces coelicolor	2	0.7673
ActVA 6 protein	Q53908	Q53908_STRCH	Streptomyces coelicolor	2	0.7673
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	3	0.7644
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	3	0.7644
Cytochrome P450 monooxygenase	Q5YNS8	Q5YNS8_NOCFA	Nocardia farcinica	3	0.7629
Cytochrome P450 monooxygenase	Q5YNS8	Q5YNS8_NOCFA	Nocardia farcinica	3	0.7629
17-beta-hydroxysteroid dehydrogenase 14	Q9BPX1	DHB14_HUMAN	Homo sapiens	2	0.7625
17-beta-hydroxysteroid dehydrogenase 14	Q9BPX1	DHB14_HUMAN	Homo sapiens	2	0.7625
Abscisic acid receptor PYL9	Q84MC7	PYL9_ARATH	Arabidopsis thaliana	3	0.7623
Abscisic acid receptor PYL9	Q84MC7	PYL9_ARATH	Arabidopsis thaliana	3	0.7623
[Pyruvate dehydrogenase (acetyl-transferring)] kinase isozyme 2, mitochondrial	Q15119	PDK2_HUMAN	Homo sapiens	3	0.7599
[Pyruvate dehydrogenase (acetyl-transferring)] kinase isozyme 2, mitochondrial	Q15119	PDK2_HUMAN	Homo sapiens	3	0.7599
Aldo-keto reductase family 1 member C1	Q04828	AK1C1_HUMAN	Homo sapiens	2	0.7581
Aldo-keto reductase family 1 member C1	Q04828	AK1C1_HUMAN	Homo sapiens	2	0.7581
Pentaerythritol tetranitrate reductase	P71278	P71278_ENTCL	Enterobacter cloacae	3	0.7581
Pentaerythritol tetranitrate reductase	P71278	P71278_ENTCL	Enterobacter cloacae	3	0.7581
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	2	0.7578
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	2	0.7578
Acetylcholinesterase	P21836	ACES_MOUSE	Mus musculus	3	0.7566
Acetylcholinesterase	P21836	ACES_MOUSE	Mus musculus	3	0.7566
Steroid Delta-isomerase	P00947	SDIS_COMTE	Comamonas testosteroni	2	0.7563
Steroid Delta-isomerase	P00947	SDIS_COMTE	Comamonas testosteroni	2	0.7563
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	2	0.7516
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	2	0.7516
Acetylcholinesterase	P04058	ACES_TETCF	Tetronarce californica	3	0.7494
Acetylcholinesterase	P04058	ACES_TETCF	Tetronarce californica	3	0.7494
Retinol-binding protein 4	P18902	RET4_BOVIN	Bos taurus	2	0.7425
Retinol-binding protein 4	P18902	RET4_BOVIN	Bos taurus	2	0.7425
Ferrochelatase, mitochondrial	P22830	HEMH_HUMAN	Homo sapiens	2	0.7416
Ferrochelatase, mitochondrial	P22830	HEMH_HUMAN	Homo sapiens	2	0.7416
Steroid 17-alpha-hydroxylase/17,20 lyase	P05093	CP17A_HUMAN	Homo sapiens	2	0.7393
Steroid 17-alpha-hydroxylase/17,20 lyase	P05093	CP17A_HUMAN	Homo sapiens	2	0.7393
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	2	0.7350
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	2	0.7350
Steroid Delta-isomerase	P00947	SDIS_COMTE	Comamonas testosteroni	2	0.7343
Steroid Delta-isomerase	P00947	SDIS_COMTE	Comamonas testosteroni	2	0.7343
Sulfotransferase 2B1	O00204	ST2B1_HUMAN	Homo sapiens	2	0.7314
Sulfotransferase 2B1	O00204	ST2B1_HUMAN	Homo sapiens	2	0.7314
cGMP-dependent 3',5'-cyclic phosphodiesterase	O00408	PDE2A_HUMAN	Homo sapiens	2	0.7313
cGMP-dependent 3',5'-cyclic phosphodiesterase	O00408	PDE2A_HUMAN	Homo sapiens	2	0.7313
Cytochrome P450 monooxygenase	Q5YNS8	Q5YNS8_NOCFA	Nocardia farcinica	3	0.7298
Cytochrome P450 monooxygenase	Q5YNS8	Q5YNS8_NOCFA	Nocardia farcinica	3	0.7298
MutT/nudix family protein	Q5SJY9	Q5SJY9_THET8	Thermus thermophilus	2	0.7294
MutT/nudix family protein	Q5SJY9	Q5SJY9_THET8	Thermus thermophilus	2	0.7294
Prostaglandin reductase 2	Q8N8N7	PTGR2_HUMAN	Homo sapiens	3	0.7291
Prostaglandin reductase 2	Q8N8N7	PTGR2_HUMAN	Homo sapiens	3	0.7291
Chalcone synthase 2	P30074	CHS2_MEDSA	Medicago sativa	2	0.7289
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	2	0.7289
Chalcone synthase 2	P30074	CHS2_MEDSA	Medicago sativa	2	0.7289
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	2	0.7289
Cytochrome P450	S6BVH1	S6BVH1_RHOER	Rhodococcus erythropolis	2	0.7285
Glutamate receptor 2	P19491	GRIA2_RAT	Rattus norvegicus	3	0.7285
Cytochrome P450	S6BVH1	S6BVH1_RHOER	Rhodococcus erythropolis	2	0.7285
Abscisic acid receptor PYL2	O80992	PYL2_ARATH	Arabidopsis thaliana	3	0.7285
Glutamate receptor 2	P19491	GRIA2_RAT	Rattus norvegicus	3	0.7285
Abscisic acid receptor PYL2	O80992	PYL2_ARATH	Arabidopsis thaliana	3	0.7285
Beta-1 adrenergic receptor	P07700	ADRB1_MELGA	Meleagris gallopavo	2	0.7275
Beta-1 adrenergic receptor	P07700	ADRB1_MELGA	Meleagris gallopavo	2	0.7275
CmeR	Q7B8P6	Q7B8P6_CAMJU	Campylobacter jejuni	2	0.7271
CmeR	Q7B8P6	Q7B8P6_CAMJU	Campylobacter jejuni	2	0.7271
Ferrochelatase, mitochondrial	P22830	HEMH_HUMAN	Homo sapiens	2	0.7254
Ferrochelatase, mitochondrial	P22830	HEMH_HUMAN	Homo sapiens	2	0.7254
12-oxophytodienoate reductase 1	Q9XG54	OPR1_SOLLC	Solanum lycopersicum	2	0.7198
12-oxophytodienoate reductase 1	Q9XG54	OPR1_SOLLC	Solanum lycopersicum	2	0.7198
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1	P04191	AT2A1_RABIT	Oryctolagus cuniculus	2	0.7194
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1	P04191	AT2A1_RABIT	Oryctolagus cuniculus	2	0.7194
Cellular retinol-binding protein type II	Q8UVG6	Q8UVG6_DANRE	Danio rerio	3	0.7190
Cellular retinol-binding protein type II	Q8UVG6	Q8UVG6_DANRE	Danio rerio	3	0.7190
Acetyl-CoA carboxylase 2	O00763	ACACB_HUMAN	Homo sapiens	3	0.7187
Acetyl-CoA carboxylase 2	O00763	ACACB_HUMAN	Homo sapiens	3	0.7187
Steroid Delta-isomerase	P07445	SDIS_PSEPU	Pseudomonas putida	2	0.7185
Steroid Delta-isomerase	P07445	SDIS_PSEPU	Pseudomonas putida	2	0.7185
CCA-adding enzyme	O28126	CCA_ARCFU	Archaeoglobus fulgidus	2	0.7181
CCA-adding enzyme	O28126	CCA_ARCFU	Archaeoglobus fulgidus	2	0.7181
Succinate dehydrogenase [ubiquinone] flavoprotein subunit, mitochondrial	Q0QF01	SDHA_PIG	Sus scrofa	2	0.7180
Succinate dehydrogenase [ubiquinone] flavoprotein subunit, mitochondrial	Q0QF01	SDHA_PIG	Sus scrofa	2	0.7180
Phospholipase A2, major isoenzyme	P00592	PA21B_PIG	Sus scrofa	3	0.7138
Phospholipase A2, major isoenzyme	P00592	PA21B_PIG	Sus scrofa	3	0.7138
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A	O76083	PDE9A_HUMAN	Homo sapiens	2	0.7137
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A	O76083	PDE9A_HUMAN	Homo sapiens	2	0.7137
Steroid 21-hydroxylase	P08686	CP21A_HUMAN	Homo sapiens	2	0.7133
Steroid 21-hydroxylase	P08686	CP21A_HUMAN	Homo sapiens	2	0.7133
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A	O76083	PDE9A_HUMAN	Homo sapiens	2	0.7128
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A	O76083	PDE9A_HUMAN	Homo sapiens	2	0.7128
Chitinase	Q54276	Q54276_SERMA	Serratia marcescens	2	0.7121
Chitinase	Q54276	Q54276_SERMA	Serratia marcescens	2	0.7121
Alcohol dehydrogenase 1C	P00326	ADH1G_HUMAN	Homo sapiens	2	0.7114
Alcohol dehydrogenase 1C	P00326	ADH1G_HUMAN	Homo sapiens	2	0.7114
Progesterone receptor	P06401	PRGR_HUMAN	Homo sapiens	3	0.7111
Progesterone receptor	P06401	PRGR_HUMAN	Homo sapiens	3	0.7111
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1	P04191	AT2A1_RABIT	Oryctolagus cuniculus	2	0.7109
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1	P04191	AT2A1_RABIT	Oryctolagus cuniculus	2	0.7109
Vitamin D3 dihydroxylase	P18326	CPXE_STRGO	Streptomyces griseolus	3	0.7090
Vitamin D3 dihydroxylase	P18326	CPXE_STRGO	Streptomyces griseolus	3	0.7090
Heat shock cognate 90 kDa protein	P54651	HSC90_DICDI	Dictyostelium discoideum	2	0.7086
Heat shock cognate 90 kDa protein	P54651	HSC90_DICDI	Dictyostelium discoideum	2	0.7086
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	2	0.7082
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	2	0.7082
17-beta-hydroxysteroid dehydrogenase type 1	P14061	DHB1_HUMAN	Homo sapiens	2	0.7064
17-beta-hydroxysteroid dehydrogenase type 1	P14061	DHB1_HUMAN	Homo sapiens	2	0.7064
17-beta-hydroxysteroid dehydrogenase type 1	P14061	DHB1_HUMAN	Homo sapiens	2	0.7052
17-beta-hydroxysteroid dehydrogenase type 1	P14061	DHB1_HUMAN	Homo sapiens	2	0.7052
Amino acid ABC transporter	D0VWX4	D0VWX4_GEOSE	Geobacillus stearothermophilus	2	0.7029
Amino acid ABC transporter	D0VWX4	D0VWX4_GEOSE	Geobacillus stearothermophilus	2	0.7029
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	2	0.7019
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	2	0.7019
Succinate dehydrogenase [ubiquinone] iron-sulfur subunit, mitochondrial	Q33862	Q33862_ASCSU	Ascaris suum	2	0.7014
Succinate dehydrogenase [ubiquinone] iron-sulfur subunit, mitochondrial	Q33862	Q33862_ASCSU	Ascaris suum	2	0.7014
ADP-ribosylation factor 1	P84080	ARF1_BOVIN	Bos taurus	2	0.7005
ADP-ribosylation factor 1	P84080	ARF1_BOVIN	Bos taurus	2	0.7005

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