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18-hydroxyvoucapan-19-al

Family: Plantae - Caesalpiniaceae
Kingdom: Plantae
Class: Terpenoid
- Subclass: Furanoditerpenoid

Canonical Smiles	O=CC[C@@]1(CO)CCC[C@]2([C@H]1CC[C@@H]1[C@@H]2Cc2c([C@@H]1C)cco2)C
InChI	InChI=1S/C21H30O3/c1-14-15-4-5-19-20(2,7-3-8-21(19,13-23)9-10-22)17(15)12-18-16(14)6-11-24-18/h6,10-11,14-15,17,19,23H,3-5,7-9,12-13H2,1-2H3/t14-,15+,17+,19-,20-,21-/m1/s1
InChIKey	PQZCSTONOODYQA-OZUCVSFASA-N
Formula	C₂₁H₃₀O₃
HBA	3
HBD	1
MW	330.47
Rotatable Bonds	3
TPSA	50.44
LogP	4.34
Number Rings	4
Number Aromatic Rings	1
Heavy Atom Count	24
Formal Charge	0
Fraction CSP3	0.76
Exact Mass	330.22
Number of Lipinski Rule Violations	0

#	Species	Family	Kingdom	NCBI Taxonomy ID
1	Stuhlmannia moavi	Caesalpiniaceae	Plantae	191956

Showing of synonyms

Odalo JO, Joseph CC, et al. (2009). Cytotoxic, anti-proliferative and antimicrobial furanoditerpenoids from Stuhlmania moavi. Phytochemistry,2009,70(17-18),2047-2052. [View] [PubMed]

No compound-protein relationship available.

SMILES: c1coc(c12)CC3C4C(CCC3C2)CCCC4

Level: 0

Mol. Weight: 330.47 g/mol

Anti-proliferative

Antibacterial

Antifungal

Cytotoxic

Absorption

Caco-2 (logPapp): -5.15
Human Oral Bioavailability 20%: Bioavailable
Human Intestinal Absorption: Absorbed
Madin-Darby Canine Kidney: -4.55
Human Oral Bioavailability 50%: Bioavailable
P-Glycoprotein Inhibitor: Non-Inhibitor
P-Glycoprotein Substrate: Non-Substrate
Skin Permeability: -2.43

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Penetrable
Fraction Unbound (Human): 0.88
Plasma Protein Binding: 71.02
Steady State Volume of Distribution: -

Metabolism

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

Excretion

Clearance: 13.52
Organic Cation Transporter 2: Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Toxic
Avian: Safe
Bee: Toxic
Bioconcentration Factor: 0.54
Biodegradation: Safe
Carcinogenesis: Toxic
Crustacean: Safe
Liver Injury I (DILI): Safe
Eye Corrosion: Safe
Eye Irritation: Safe
Maximum Tolerated Dose: 0.05
Liver Injury II: Safe
hERG Blockers: Toxic
Daphnia Maga: 6.81
Micronucleos: Safe
NR-AhR: Safe
NR-AR: Toxic
NR-AR-LBD: Safe
NR-Aromatase: Safe
NR-ER: Toxic
NR-ER-LBD: Safe
NR-GR: Toxic
NR-PPAR-gamma: Safe
NR-TR: Toxic
T. Pyriformis: -1.8
Rat (Acute): 3.28
Rat (Chronic Oral): 1.95
Fathead Minnow: 3.92
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: 401.53
Hydration Free Energy: -5.59
Log(D) at pH=7.4: 3.3
Log(P): 3.81
Log S: -4.24
Log(Vapor Pressure): -8.28
Melting Point: 136.71
pKa Acid: 9.01
pKa Basic: 6.4

Protein Name	UniProt ID	Entry Name	Species	#Pharmacophore Points	Probability (0.7 ≤ Tversky Score ≤ 1.0)
Glutamate receptor 2	P19491	GRIA2_RAT	Rattus norvegicus	3	0.8268
Glutamate receptor 2	P19491	GRIA2_RAT	Rattus norvegicus	3	0.8268
Pentaerythritol tetranitrate reductase	P71278	P71278_ENTCL	Enterobacter cloacae	3	0.7789
Pentaerythritol tetranitrate reductase	P71278	P71278_ENTCL	Enterobacter cloacae	3	0.7789
Lactoylglutathione lyase	Q9CPU0	LGUL_MOUSE	Mus musculus	2	0.7776
Lactoylglutathione lyase	Q9CPU0	LGUL_MOUSE	Mus musculus	2	0.7776
17-beta-hydroxysteroid dehydrogenase type 1	P14061	DHB1_HUMAN	Homo sapiens	3	0.7751
17-beta-hydroxysteroid dehydrogenase type 1	P14061	DHB1_HUMAN	Homo sapiens	3	0.7751
Bifunctional dihydrofolate reductase-thymidylate synthase	P13922	DRTS_PLAFK	Plasmodium falciparum	2	0.7744
Bifunctional dihydrofolate reductase-thymidylate synthase	P13922	DRTS_PLAFK	Plasmodium falciparum	2	0.7744
17-beta-hydroxysteroid dehydrogenase type 1	P14061	DHB1_HUMAN	Homo sapiens	3	0.7712
17-beta-hydroxysteroid dehydrogenase type 1	P14061	DHB1_HUMAN	Homo sapiens	3	0.7712
Steroid Delta-isomerase	P07445	SDIS_PSEPU	Pseudomonas putida	2	0.7686
Steroid Delta-isomerase	P07445	SDIS_PSEPU	Pseudomonas putida	2	0.7686
Steroid Delta-isomerase	P07445	SDIS_PSEPU	Pseudomonas putida	2	0.7597
Steroid Delta-isomerase	P07445	SDIS_PSEPU	Pseudomonas putida	2	0.7597
Photosynthetic reaction center cytochrome c subunit	P07173	CYCR_BLAVI	Blastochloris viridis	3	0.7585
Photosynthetic reaction center cytochrome c subunit	P07173	CYCR_BLAVI	Blastochloris viridis	3	0.7585
Tetracycline repressor protein class D	P0ACT4	TETR4_ECOLX	Escherichia coli	3	0.7567
Tetracycline repressor protein class D	P0ACT4	TETR4_ECOLX	Escherichia coli	3	0.7567
Ferrochelatase, mitochondrial	P22830	HEMH_HUMAN	Homo sapiens	3	0.7548
Ferrochelatase, mitochondrial	P22830	HEMH_HUMAN	Homo sapiens	3	0.7548
Acetylcholinesterase	P04058	ACES_TETCF	Tetronarce californica	3	0.7532
Acetylcholinesterase	P04058	ACES_TETCF	Tetronarce californica	3	0.7532
Soluble acetylcholine receptor	Q8WSF8	Q8WSF8_APLCA	Aplysia californica	3	0.7531
Soluble acetylcholine receptor	Q8WSF8	Q8WSF8_APLCA	Aplysia californica	3	0.7531
Steroid Delta-isomerase	P07445	SDIS_PSEPU	Pseudomonas putida	2	0.7485
Steroid Delta-isomerase	P07445	SDIS_PSEPU	Pseudomonas putida	2	0.7485
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	2	0.7450
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	2	0.7450
Carminomycin 4-O-methyltransferase DnrK	Q06528	DNRK_STRPE	Streptomyces peucetius	2	0.7374
Carminomycin 4-O-methyltransferase DnrK	Q06528	DNRK_STRPE	Streptomyces peucetius	2	0.7374
NADH:flavin oxidoreductase Sye1	Q8EEC8	Q8EEC8_SHEON	Shewanella oneidensis	2	0.7356
NADH:flavin oxidoreductase Sye1	Q8EEC8	Q8EEC8_SHEON	Shewanella oneidensis	2	0.7356
17-beta-hydroxysteroid dehydrogenase type 1	P14061	DHB1_HUMAN	Homo sapiens	3	0.7329
17-beta-hydroxysteroid dehydrogenase type 1	P14061	DHB1_HUMAN	Homo sapiens	3	0.7329
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	2	0.7253
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	2	0.7253
Steroid Delta-isomerase	P07445	SDIS_PSEPU	Pseudomonas putida	2	0.7243
Steroid Delta-isomerase	P07445	SDIS_PSEPU	Pseudomonas putida	2	0.7243
Aldo-keto reductase family 1 member B1	P80276	ALDR_PIG	Sus scrofa	2	0.7230
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	2	0.7230
Aldo-keto reductase family 1 member B1	P80276	ALDR_PIG	Sus scrofa	2	0.7230
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	2	0.7230
17-beta-hydroxysteroid dehydrogenase type 1	P14061	DHB1_HUMAN	Homo sapiens	3	0.7201
17-beta-hydroxysteroid dehydrogenase type 1	P14061	DHB1_HUMAN	Homo sapiens	3	0.7201
17-beta-hydroxysteroid dehydrogenase type 1	P14061	DHB1_HUMAN	Homo sapiens	3	0.7198
17-beta-hydroxysteroid dehydrogenase type 1	P14061	DHB1_HUMAN	Homo sapiens	3	0.7198
Aldo-keto reductase family 1 member C2	P52895	AK1C2_HUMAN	Homo sapiens	2	0.7189
Aldo-keto reductase family 1 member C2	P52895	AK1C2_HUMAN	Homo sapiens	2	0.7189
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	3	0.7163
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	3	0.7163
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	2	0.7139
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	2	0.7139
Ferrochelatase, mitochondrial	P22830	HEMH_HUMAN	Homo sapiens	3	0.7115
Ferrochelatase, mitochondrial	P22830	HEMH_HUMAN	Homo sapiens	3	0.7115
Aldo-keto reductase family 1 member B1	P15121	ALDR_HUMAN	Homo sapiens	2	0.7113
Aldo-keto reductase family 1 member B1	P15121	ALDR_HUMAN	Homo sapiens	2	0.7113
Retinol dehydratase	Q26490	Q26490_SPOFR	Spodoptera frugiperda	3	0.7101
Steroid Delta-isomerase	P07445	SDIS_PSEPU	Pseudomonas putida	2	0.7101
Retinol dehydratase	Q26490	Q26490_SPOFR	Spodoptera frugiperda	3	0.7101
Steroid Delta-isomerase	P07445	SDIS_PSEPU	Pseudomonas putida	2	0.7101
Aldo-keto reductase family 1 member C2	P52895	AK1C2_HUMAN	Homo sapiens	2	0.7090
Aldo-keto reductase family 1 member C2	P52895	AK1C2_HUMAN	Homo sapiens	2	0.7090
Neocarzinostatin	P0A3R9	NCZS_STRCZ	Streptomyces carzinostaticus	3	0.7067
Neocarzinostatin	P0A3R9	NCZS_STRCZ	Streptomyces carzinostaticus	3	0.7067
17-beta-hydroxysteroid dehydrogenase type 1	P14061	DHB1_HUMAN	Homo sapiens	3	0.7059
17-beta-hydroxysteroid dehydrogenase type 1	P14061	DHB1_HUMAN	Homo sapiens	3	0.7059
ATP-dependent molecular chaperone HSP82	P02829	HSP82_YEAST	Saccharomyces cerevisiae	3	0.7015
ATP-dependent molecular chaperone HSP82	P02829	HSP82_YEAST	Saccharomyces cerevisiae	3	0.7015
Pteridine reductase	O76290	O76290_TRYBB	Trypanosoma brucei brucei	2	0.7008
Pteridine reductase	O76290	O76290_TRYBB	Trypanosoma brucei brucei	2	0.7008
CmeR	Q7B8P6	Q7B8P6_CAMJU	Campylobacter jejuni	3	0.7004
CmeR	Q7B8P6	Q7B8P6_CAMJU	Campylobacter jejuni	3	0.7004

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