ANPDB

Select a section from the left sidebar

Otostegindiol

Family: Plantae - Lamiaceae
Kingdom: Plantae
Class: Terpenoid
- Subclass: Labdane Diterpenoid

Canonical Smiles	C[C@@H]1CC[C@@H]2[C@@]([C@@]1(O)CCc1cocc1)(C)CC[C@H](C2(C)C)O
InChI	InChI=1S/C20H32O3/c1-14-5-6-16-18(2,3)17(21)8-10-19(16,4)20(14,22)11-7-15-9-12-23-13-15/h9,12-14,16-17,21-22H,5-8,10-11H2,1-4H3/t14-,16+,17-,19-,20-/m1/s1
InChIKey	NWVJHHNURGENGL-NZODBCNPSA-N
Formula	C₂₀H₃₂O₃
HBA	3
HBD	2
MW	320.47
Rotatable Bonds	3
TPSA	53.6
LogP	4.18
Number Rings	3
Number Aromatic Rings	1
Heavy Atom Count	23
Formal Charge	0
Fraction CSP3	0.8
Exact Mass	320.24
Number of Lipinski Rule Violations	0

#	Species	Family	Kingdom	NCBI Taxonomy ID
1	Otostegia integrifolia	Lamiaceae	Plantae	483857

Showing of synonyms

Endale A, Bisrat D, et al. (2013). In vivo antimalarial activity of a labdane diterpenoid from the leaves of Otostegia integrifolia Benth.. Phytotherapy Research,2013,27(12),1805-1809. [View] [PubMed]

No compound-protein relationship available.

SMILES: c1occc1CCC2CCCC(C23)CCCC3

Level: 1

Mol. Weight: 320.47 g/mol

SMILES: C1CCCC(C12)CCCC2

Level: 0

Mol. Weight: 320.47 g/mol

SMILES: c1ccoc1

Level: 0

Mol. Weight: 320.47 g/mol

Antimalarial

Absorption

Caco-2 (logPapp): -4.82
Human Oral Bioavailability 20%: Bioavailable
Human Intestinal Absorption: Absorbed
Madin-Darby Canine Kidney: -4.41
Human Oral Bioavailability 50%: Bioavailable
P-Glycoprotein Inhibitor: Inhibitor
P-Glycoprotein Substrate: Non-Substrate
Skin Permeability: -2.69

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Penetrable
Fraction Unbound (Human): 0.78
Plasma Protein Binding: 67.16
Steady State Volume of Distribution: -

Metabolism

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

Excretion

Clearance: 11.58
Organic Cation Transporter 2: Non-Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Safe
Avian: Safe
Bee: Toxic
Bioconcentration Factor: 0.6
Biodegradation: Safe
Carcinogenesis: Toxic
Crustacean: Safe
Liver Injury I (DILI): Safe
Eye Corrosion: Safe
Eye Irritation: Safe
Maximum Tolerated Dose: -0.36
Liver Injury II: Safe
hERG Blockers: Toxic
Daphnia Maga: 5.52
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: Toxic
T. Pyriformis: -2.2
Rat (Acute): 2.69
Rat (Chronic Oral): 1.78
Fathead Minnow: 3.85
Respiratory Disease: Toxic
Skin Sensitisation: Toxic
SR-ARE: Safe
SR-ATAD5: Safe
SR-HSE: Safe
SR-MMP: Safe
SR-p53: Safe

General Properties

Boiling Point: 361.26
Hydration Free Energy: -6.23
Log(D) at pH=7.4: 3.69
Log(P): 3.9
Log S: -3.77
Log(Vapor Pressure): -6.75
Melting Point: 128.48
pKa Acid: 9.99
pKa Basic: 8.11

Protein Name	UniProt ID	Entry Name	Species	#Pharmacophore Points	Probability (0.7 ≤ Tversky Score ≤ 1.0)
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1	P04191	AT2A1_RABIT	Oryctolagus cuniculus	3	0.8648
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1	P04191	AT2A1_RABIT	Oryctolagus cuniculus	3	0.8648
Neocarzinostatin	P0A3R9	NCZS_STRCZ	Streptomyces carzinostaticus	3	0.8594
Neocarzinostatin	P0A3R9	NCZS_STRCZ	Streptomyces carzinostaticus	3	0.8594
CmeR	Q7B8P6	Q7B8P6_CAMJU	Campylobacter jejuni	3	0.8162
CmeR	Q7B8P6	Q7B8P6_CAMJU	Campylobacter jejuni	3	0.8162
Retinol dehydratase	Q26490	Q26490_SPOFR	Spodoptera frugiperda	3	0.7999
Retinol dehydratase	Q26490	Q26490_SPOFR	Spodoptera frugiperda	3	0.7999
Aldo-keto reductase family 1 member C2	P52895	AK1C2_HUMAN	Homo sapiens	2	0.7855
Aldo-keto reductase family 1 member C2	P52895	AK1C2_HUMAN	Homo sapiens	2	0.7855
Lactoylglutathione lyase	Q9CPU0	LGUL_MOUSE	Mus musculus	2	0.7699
Lactoylglutathione lyase	Q9CPU0	LGUL_MOUSE	Mus musculus	2	0.7699
Sulfotransferase 2B1	O00204	ST2B1_HUMAN	Homo sapiens	2	0.7671
Sulfotransferase 2B1	O00204	ST2B1_HUMAN	Homo sapiens	2	0.7671
Steroid Delta-isomerase	P07445	SDIS_PSEPU	Pseudomonas putida	2	0.7665
Steroid Delta-isomerase	P07445	SDIS_PSEPU	Pseudomonas putida	2	0.7665
Aldo-keto reductase family 1 member C2	P52895	AK1C2_HUMAN	Homo sapiens	2	0.7655
Aldo-keto reductase family 1 member C2	P52895	AK1C2_HUMAN	Homo sapiens	2	0.7655
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	2	0.7588
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	2	0.7588
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	2	0.7569
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	2	0.7569
Beta-1 adrenergic receptor	P07700	ADRB1_MELGA	Meleagris gallopavo	3	0.7547
Beta-1 adrenergic receptor	P07700	ADRB1_MELGA	Meleagris gallopavo	3	0.7547
Aldo-keto reductase family 1 member C3	P42330	AK1C3_HUMAN	Homo sapiens	2	0.7531
Aldo-keto reductase family 1 member C3	P42330	AK1C3_HUMAN	Homo sapiens	2	0.7531
Bifunctional dihydrofolate reductase-thymidylate synthase	P13922	DRTS_PLAFK	Plasmodium falciparum	2	0.7515
Bifunctional dihydrofolate reductase-thymidylate synthase	P13922	DRTS_PLAFK	Plasmodium falciparum	2	0.7515
Probable NDP-rhamnosyltransferase	Q9ALM8	Q9ALM8_SACSN	Saccharopolyspora spinosa	3	0.7492
Probable NDP-rhamnosyltransferase	Q9ALM8	Q9ALM8_SACSN	Saccharopolyspora spinosa	3	0.7492
Nuclear receptor subfamily 1 group I member 2	O75469	NR1I2_HUMAN	Homo sapiens	3	0.7482
Nuclear receptor subfamily 1 group I member 2	O75469	NR1I2_HUMAN	Homo sapiens	3	0.7482
Aldo-keto reductase family 1 member C1	Q04828	AK1C1_HUMAN	Homo sapiens	2	0.7477
Aldo-keto reductase family 1 member C1	Q04828	AK1C1_HUMAN	Homo sapiens	2	0.7477
NADH:flavin oxidoreductase Sye1	Q8EEC8	Q8EEC8_SHEON	Shewanella oneidensis	2	0.7461
NADH:flavin oxidoreductase Sye1	Q8EEC8	Q8EEC8_SHEON	Shewanella oneidensis	2	0.7461
Sulfide-quinone reductase	B7JBP8	SQRD_ACIF2	Acidithiobacillus ferrooxidans)	3	0.7457
Sulfide-quinone reductase	B7JBP8	SQRD_ACIF2	Acidithiobacillus ferrooxidans)	3	0.7457
Steroid Delta-isomerase	P07445	SDIS_PSEPU	Pseudomonas putida	2	0.7433
Steroid Delta-isomerase	P07445	SDIS_PSEPU	Pseudomonas putida	2	0.7433
Carminomycin 4-O-methyltransferase DnrK	Q06528	DNRK_STRPE	Streptomyces peucetius	2	0.7401
Carminomycin 4-O-methyltransferase DnrK	Q06528	DNRK_STRPE	Streptomyces peucetius	2	0.7401
Retinoic acid receptor RXR-alpha	P19793	RXRA_HUMAN	Homo sapiens	3	0.7378
Retinoic acid receptor RXR-alpha	P19793	RXRA_HUMAN	Homo sapiens	3	0.7378
Aldo-keto reductase family 1 member C3	P42330	AK1C3_HUMAN	Homo sapiens	3	0.7377
Aldo-keto reductase family 1 member C3	P42330	AK1C3_HUMAN	Homo sapiens	3	0.7377
Steroid Delta-isomerase	P07445	SDIS_PSEPU	Pseudomonas putida	2	0.7369
Steroid Delta-isomerase	P07445	SDIS_PSEPU	Pseudomonas putida	2	0.7369
Beta-elicitin cryptogein	P15570	ELIB_PHYCR	Phytophthora cryptogea	3	0.7365
Beta-elicitin cryptogein	P15570	ELIB_PHYCR	Phytophthora cryptogea	3	0.7365
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1	P04191	AT2A1_RABIT	Oryctolagus cuniculus	2	0.7354
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1	P04191	AT2A1_RABIT	Oryctolagus cuniculus	2	0.7354
Lanosterol 14-alpha-demethylase	Q385E8	Q385E8_TRYB2	Trypanosoma brucei brucei	3	0.7334
Lanosterol 14-alpha-demethylase	Q385E8	Q385E8_TRYB2	Trypanosoma brucei brucei	3	0.7334
Bifunctional epoxide hydrolase 2	P34913	HYES_HUMAN	Homo sapiens	2	0.7264
Bifunctional epoxide hydrolase 2	P34913	HYES_HUMAN	Homo sapiens	2	0.7264
Acetyl-CoA carboxylase 2	O00763	ACACB_HUMAN	Homo sapiens	3	0.7202
Acetyl-CoA carboxylase 2	O00763	ACACB_HUMAN	Homo sapiens	3	0.7202
Prothrombin	P00734	THRB_HUMAN	Homo sapiens	3	0.7188
Prothrombin	P00734	THRB_HUMAN	Homo sapiens	3	0.7188
Carbonic anhydrase 1	P00915	CAH1_HUMAN	Homo sapiens	2	0.7168
Carbonic anhydrase 1	P00915	CAH1_HUMAN	Homo sapiens	2	0.7168
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	2	0.7162
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	2	0.7162
Tetracycline repressor protein class D	P0ACT4	TETR4_ECOLX	Escherichia coli	3	0.7153
Tetracycline repressor protein class D	P0ACT4	TETR4_ECOLX	Escherichia coli	3	0.7153
Retinol-binding protein 1	P09455	RET1_HUMAN	Homo sapiens	3	0.7137
Retinol-binding protein 1	P09455	RET1_HUMAN	Homo sapiens	3	0.7137
[Pyruvate dehydrogenase (acetyl-transferring)] kinase isozyme 2, mitochondrial	Q15119	PDK2_HUMAN	Homo sapiens	3	0.7123
[Pyruvate dehydrogenase (acetyl-transferring)] kinase isozyme 2, mitochondrial	Q15119	PDK2_HUMAN	Homo sapiens	3	0.7123
Chitinase A	Q9AMP1	Q9AMP1_VIBHA	Vibrio harveyi	2	0.7103
Chitinase A	Q9AMP1	Q9AMP1_VIBHA	Vibrio harveyi	2	0.7103
Lanosterol synthase	P48449	ERG7_HUMAN	Homo sapiens	3	0.7079
Lanosterol synthase	P48449	ERG7_HUMAN	Homo sapiens	3	0.7079
Steroid Delta-isomerase	P07445	SDIS_PSEPU	Pseudomonas putida	2	0.7050
Steroid Delta-isomerase	P07445	SDIS_PSEPU	Pseudomonas putida	2	0.7050
Acetylcholinesterase	P21836	ACES_MOUSE	Mus musculus	2	0.7029
Acetylcholinesterase	P21836	ACES_MOUSE	Mus musculus	2	0.7029
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A	O76083	PDE9A_HUMAN	Homo sapiens	2	0.7027
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A	O76083	PDE9A_HUMAN	Homo sapiens	2	0.7027
glutaryl-CoA dehydrogenase (ETF)	Q3JP94	Q3JP94_BURP1	Burkholderia pseudomallei	2	0.7013
glutaryl-CoA dehydrogenase (ETF)	Q3JP94	Q3JP94_BURP1	Burkholderia pseudomallei	2	0.7013
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	2	0.7006
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	2	0.7006

Download SDF