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2beta-hydroxyhardwickiic acid

Family: Sapindaceae
Kingdom: Plantae
Class: Terpenoid
- Subclass: Clerodane Diterpenoid

Canonical Smiles	O[C@@H]1C=C(C(=O)O)[C@]2([C@H](C1)[C@@](C)(CCc1cocc1)[C@@H](CC2)C)C
InChI	InChI=1S/C20H28O4/c1-13-4-7-20(3)16(18(22)23)10-15(21)11-17(20)19(13,2)8-5-14-6-9-24-12-14/h6,9-10,12-13,15,17,21H,4-5,7-8,11H2,1-3H3,(H,22,23)/t13-,15-,17-,19+,20+/m1/s1
InChIKey	VVCXPQBVJROEEN-RPELPBHHSA-N
Formula	C₂₀H₂₈O₄
HBA	3
HBD	2
MW	332.44
Rotatable Bonds	4
TPSA	70.67
LogP	4.05
Number Rings	3
Number Aromatic Rings	1
Heavy Atom Count	24
Formal Charge	0
Fraction CSP3	0.65
Exact Mass	332.2
Number of Lipinski Rule Violations	0

#	Species	Family	Kingdom	NCBI Taxonomy ID
1	Dodonaea angustifolia	Sapindaceae	Plantae	379228

Showing of synonyms

Omosa LK, Amugune B, et al. (2014). Antimicrobial flavonoids and diterpenoids from Dodonaea angustifolia. South African Journal of Botany,2014,91,58-62. [View] [PubMed]

Pubchem: 14021511

Zinc: ZINC000071404379

Nmrshiftdb2: 70020418

No compound-protein relationship available.

SMILES: c1occc1CCC(CCC2)C(C23)CCC=C3

Level: 1

Mol. Weight: 230.35 g/mol

SMILES: C1=CCCC(C12)CCCC2

Level: 0

Mol. Weight: 136.24 g/mol

SMILES: c1ccoc1

Level: 0

Mol. Weight: 68.07 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp): -4.86
Human Oral Bioavailability 20%: Bioavailable
Human Intestinal Absorption: Absorbed
Madin-Darby Canine Kidney: -4.77
Human Oral Bioavailability 50%: Non-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): 0.89
Plasma Protein Binding: 78.25
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: Non-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: 3.18
Organic Cation Transporter 2: Non-Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Safe
Avian: Safe
Bee: Toxic
Bioconcentration Factor: -0.11
Biodegradation: Safe
Carcinogenesis: Toxic
Crustacean: Safe
Liver Injury I (DILI): Safe
Eye Corrosion: Safe
Eye Irritation: Safe
Maximum Tolerated Dose: -0.21
Liver Injury II: Toxic
hERG Blockers: Safe
Daphnia Maga: 3.08
Micronucleos: Safe
NR-AhR: Safe
NR-AR: Safe
NR-AR-LBD: Safe
NR-Aromatase: Safe
NR-ER: Safe
NR-ER-LBD: Safe
NR-GR: Toxic
NR-PPAR-gamma: Safe
NR-TR: Safe
T. Pyriformis: -2.1
Rat (Acute): 2.68
Rat (Chronic Oral): 2.28
Fathead Minnow: 3.99
Respiratory Disease: Toxic
Skin Sensitisation: Safe
SR-ARE: Safe
SR-ATAD5: Safe
SR-HSE: Safe
SR-MMP: Safe
SR-p53: Safe

General Properties

Boiling Point: 370.22
Hydration Free Energy: -6.56
Log(D) at pH=7.4: 1.37
Log(P): 3.75
Log S: -4.14
Log(Vapor Pressure): -8.23
Melting Point: 158.36
pKa Acid: 4.13
pKa Basic: 7.42

Protein Name	UniProt ID	Entry Name	Species	#Pharmacophore Points	Probability (0.7 ≤ Tversky Score ≤ 1.0)
Tetracycline repressor protein class D	P0ACT4	TETR4_ECOLX	Escherichia coli	3	0.8779
Tetracycline repressor protein class D	P0ACT4	TETR4_ECOLX	Escherichia coli	3	0.8779
ABC-type polar amino acid transport system, ATPase component	Q8RCC2	Q8RCC2_CALS4	Caldanaerobacter subterraneus subsp. tengcongensis	3	0.8560
ABC-type polar amino acid transport system, ATPase component	Q8RCC2	Q8RCC2_CALS4	Caldanaerobacter subterraneus subsp. tengcongensis	3	0.8560
Photosynthetic reaction center cytochrome c subunit	P07173	CYCR_BLAVI	Blastochloris viridis	3	0.8544
Photosynthetic reaction center cytochrome c subunit	P07173	CYCR_BLAVI	Blastochloris viridis	3	0.8544
Sterol 14alpha-demethylase	P9WPP9	CP51_MYCTU	Mycobacterium tuberculosis	3	0.8493
Sterol 14alpha-demethylase	P9WPP9	CP51_MYCTU	Mycobacterium tuberculosis	3	0.8493
Tetracycline repressor protein class D	P0ACT4	TETR4_ECOLX	Escherichia coli	3	0.8432
Tetracycline repressor protein class D	P0ACT4	TETR4_ECOLX	Escherichia coli	3	0.8432
Tetracycline repressor protein class D	P0ACT4	TETR4_ECOLX	Escherichia coli	3	0.8197
Tetracycline repressor protein class D	P0ACT4	TETR4_ECOLX	Escherichia coli	3	0.8197
Carboxyethyl-arginine beta-lactam-synthase	P0DJQ7	BLS_STRCL	Streptomyces clavuligerus	3	0.8000
Carboxyethyl-arginine beta-lactam-synthase	P0DJQ7	BLS_STRCL	Streptomyces clavuligerus	3	0.8000
Lactoylglutathione lyase	Q9CPU0	LGUL_MOUSE	Mus musculus	2	0.7982
Lactoylglutathione lyase	Q9CPU0	LGUL_MOUSE	Mus musculus	2	0.7982
Metallo-beta-lactamase type 2	C7C422	BLAN1_KLEPN	Klebsiella pneumoniae	3	0.7943
Metallo-beta-lactamase type 2	C7C422	BLAN1_KLEPN	Klebsiella pneumoniae	3	0.7943
Steroid Delta-isomerase	P00947	SDIS_COMTE	Comamonas testosteroni	2	0.7898
Steroid Delta-isomerase	P00947	SDIS_COMTE	Comamonas testosteroni	2	0.7898
Streptavidin	P22629	SAV_STRAV	Streptomyces avidinii	2	0.7894
Streptavidin	P22629	SAV_STRAV	Streptomyces avidinii	2	0.7894
Aldo-keto reductase family 1 member C2	P52895	AK1C2_HUMAN	Homo sapiens	2	0.7803
Aldo-keto reductase family 1 member C2	P52895	AK1C2_HUMAN	Homo sapiens	2	0.7803
Aldo-keto reductase family 1 member C2	P52895	AK1C2_HUMAN	Homo sapiens	2	0.7802
Aldo-keto reductase family 1 member C2	P52895	AK1C2_HUMAN	Homo sapiens	2	0.7802
Steroid Delta-isomerase	P07445	SDIS_PSEPU	Pseudomonas putida	2	0.7693
Steroid Delta-isomerase	P07445	SDIS_PSEPU	Pseudomonas putida	2	0.7693
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A	O76083	PDE9A_HUMAN	Homo sapiens	2	0.7679
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A	O76083	PDE9A_HUMAN	Homo sapiens	2	0.7679
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	2	0.7678
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	2	0.7678
Branched-chain-amino-acid aminotransferase, mitochondrial	O15382	BCAT2_HUMAN	Homo sapiens	3	0.7575
Branched-chain-amino-acid aminotransferase, mitochondrial	O15382	BCAT2_HUMAN	Homo sapiens	3	0.7575
Soluble acetylcholine receptor	Q8WSF8	Q8WSF8_APLCA	Aplysia californica	3	0.7556
Soluble acetylcholine receptor	Q8WSF8	Q8WSF8_APLCA	Aplysia californica	3	0.7556
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	2	0.7500
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	2	0.7500
Mycinamicin III 3''-O-methyltransferase	Q49492	MYCF_MICGR	Micromonospora griseorubida	3	0.7350
Mycinamicin III 3''-O-methyltransferase	Q49492	MYCF_MICGR	Micromonospora griseorubida	3	0.7350
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A	O76083	PDE9A_HUMAN	Homo sapiens	2	0.7333
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A	O76083	PDE9A_HUMAN	Homo sapiens	2	0.7333
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	2	0.7289
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	2	0.7289
cGMP-dependent 3',5'-cyclic phosphodiesterase	O00408	PDE2A_HUMAN	Homo sapiens	2	0.7288
cGMP-dependent 3',5'-cyclic phosphodiesterase	O00408	PDE2A_HUMAN	Homo sapiens	2	0.7288
Ribonuclease 4	P15468	RNAS4_PIG	Sus scrofa	3	0.7275
Ribonuclease 4	P15468	RNAS4_PIG	Sus scrofa	3	0.7275
Aldo-keto reductase family 1 member C2	P52895	AK1C2_HUMAN	Homo sapiens	2	0.7273
Aldo-keto reductase family 1 member C2	P52895	AK1C2_HUMAN	Homo sapiens	2	0.7273
Chalcone synthase 2	P30074	CHS2_MEDSA	Medicago sativa	2	0.7263
NADPH-dependent oxidoreductase 2-alkenal reductase	Q39172	AER_ARATH	Arabidopsis thaliana	2	0.7263
NADPH-dependent oxidoreductase 2-alkenal reductase	Q39172	AER_ARATH	Arabidopsis thaliana	2	0.7263
Chalcone synthase 2	P30074	CHS2_MEDSA	Medicago sativa	2	0.7263
Methionine aminopeptidase 1	P53582	MAP11_HUMAN	Homo sapiens	3	0.7255
Methionine aminopeptidase 1	P53582	MAP11_HUMAN	Homo sapiens	3	0.7255
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1	P04191	AT2A1_RABIT	Oryctolagus cuniculus	3	0.7242
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1	P04191	AT2A1_RABIT	Oryctolagus cuniculus	3	0.7242
Hydroxymethylglutaryl-CoA synthase	Q9FD71	HMGCS_ENTFL	Enterococcus faecalis	2	0.7134
Hydroxymethylglutaryl-CoA synthase	Q9FD71	HMGCS_ENTFL	Enterococcus faecalis	2	0.7134
Deacetoxycephalosporin C synthase	P18548	CEFE_STRCL	Streptomyces clavuligerus	3	0.7109
Deacetoxycephalosporin C synthase	P18548	CEFE_STRCL	Streptomyces clavuligerus	3	0.7109
Genome polyprotein	Q2YHF0	POLG_DEN4T	Dengue virus type 4	3	0.7074
Genome polyprotein	Q2YHF0	POLG_DEN4T	Dengue virus type 4	3	0.7074
Chloramphenicol acetyltransferase	P62577	CAT_ECOLX	Escherichia coli	3	0.7071
Chloramphenicol acetyltransferase	P62577	CAT_ECOLX	Escherichia coli	3	0.7071
Sulfide-quinone reductase	B7JBP8	SQRD_ACIF2	Acidithiobacillus ferrooxidans)	2	0.7070
Sulfide-quinone reductase	B7JBP8	SQRD_ACIF2	Acidithiobacillus ferrooxidans)	2	0.7070
Abscisic acid receptor PYL3	Q9SSM7	PYL3_ARATH	Arabidopsis thaliana	3	0.7053
Abscisic acid receptor PYL3	Q9SSM7	PYL3_ARATH	Arabidopsis thaliana	3	0.7053
Carbonic anhydrase 4	Q64444	CAH4_MOUSE	Mus musculus	2	0.7045
Carbonic anhydrase 4	Q64444	CAH4_MOUSE	Mus musculus	2	0.7045
ATP-dependent molecular chaperone HSP82	P02829	HSP82_YEAST	Saccharomyces cerevisiae	2	0.7031
ATP-dependent molecular chaperone HSP82	P02829	HSP82_YEAST	Saccharomyces cerevisiae	2	0.7031
Poly [ADP-ribose] polymerase 1	P09874	PARP1_HUMAN	Homo sapiens	3	0.7030
Poly [ADP-ribose] polymerase 1	P09874	PARP1_HUMAN	Homo sapiens	3	0.7030

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