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4beta,8beta,14beta-trihydroxy-5beta,6beta-epoxy-2alpha-O,3beta-O-[(2’beta,3’beta-methylenedioxy-4′-desoxy-5′-dehydroxymethyl-hexosulose]-card-20(22)-enolide

Family: Plantae - Celastraceae
Kingdom: Plantae
Class: Steroid

Canonical Smiles	CO[C@H]1CC(C)O[C@@H]2[C@@]1(O)O[C@@H]1C[C@@]3(C)C(=C[C@H]1O2)CCC1C3CC[C@]2([C@]1(O)CC[C@@H]2C1=CC(=O)OC1)C
InChI	InChI=1S/C30H42O8/c1-16-11-24(34-4)30(33)26(36-16)37-22-13-18-5-6-21-20(27(18,2)14-23(22)38-30)7-9-28(3)19(8-10-29(21,28)32)17-12-25(31)35-15-17/h12-13,16,19-24,26,32-33H,5-11,14-15H2,1-4H3/t16?,19-,20?,21?,22-,23-,24+,26+,27+,28-,29+,30+/m1/s1
InChIKey	BEWNMBOZHCLTKT-LLMTXIQKSA-N
Formula	C₃₀H₄₂O₈
HBA	8
HBD	2
MW	530.66
Rotatable Bonds	2
TPSA	103.68
LogP	3.4
Number Rings	7
Number Aromatic Rings	0
Heavy Atom Count	38
Formal Charge	0
Fraction CSP3	0.83
Exact Mass	530.29
Number of Lipinski Rule Violations	1

#	Species	Family	Kingdom	NCBI Taxonomy ID
1	Salacia staudtiana	Celastraceae	Plantae	662028

Showing of synonyms

Kamtcha DW, Tene M, et al. (2018). Cardenolides and dihydro-β-agarofuran sesquiterpenes from the seeds of Salacia staudtiana.. Fitoterapia,2018, 131, 174-181. [View] [PubMed]

No compound-protein relationship available.

SMILES: C1OC(=O)C=C1C2CCC(C23)C4C(CC3)C5C(CC4)=CC6C(C5)OC7C(O6)OCCC7

Level: 1

Mol. Weight: 530.66 g/mol

SMILES: C1CCC(C12)CCC3C2CCC=4C3CC5C(C4)OC6C(O5)CCCO6

Level: 0

Mol. Weight: 530.66 g/mol

SMILES: O=C1C=CCO1

Level: 0

Mol. Weight: 530.66 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp): -5.15
Human Oral Bioavailability 20%: Bioavailable
Human Intestinal Absorption: Absorbed
Madin-Darby Canine Kidney: -4.830
Human Oral Bioavailability 50%: Bioavailable
P-Glycoprotein Inhibitor: Non-Inhibitor
P-Glycoprotein Substrate: Substrate
Skin Permeability: -0.42

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Penetrable
Fraction Unbound (Human): 0.990
Plasma Protein Binding: 61.03
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: Non-Substrate
CYP 2D6 Inhibitor: Non-Inhibitor
CYP 2D6 Substrate: Non-Substrate
CYP 3A4 Inhibitor: Non-Inhibitor
CYP 3A4 Substrate: Substrate
OATP1B1: Non-Inhibitor
OATP1B3: Non-Inhibitor

Excretion

Clearance: 6.020
Organic Cation Transporter 2: Non-Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Safe
Avian: Safe
Bee: Toxic
Bioconcentration Factor: -1.420
Biodegradation: Safe
Carcinogenesis: Safe
Crustacean: Safe
Liver Injury I (DILI): Safe
Eye Corrosion: Safe
Eye Irritation: Safe
Maximum Tolerated Dose: -2.580
Liver Injury II: Toxic
hERG Blockers: Toxic
Daphnia Maga: 7.500
Micronucleos: Toxic
NR-AhR: Safe
NR-AR: Safe
NR-AR-LBD: Toxic
NR-Aromatase: Toxic
NR-ER: Toxic
NR-ER-LBD: Safe
NR-GR: Toxic
NR-PPAR-gamma: Safe
NR-TR: Toxic
T. Pyriformis: -2826.740
Rat (Acute): 4.100
Rat (Chronic Oral): 1.660
Fathead Minnow: 10.660
Respiratory Disease: Toxic
Skin Sensitisation: Toxic
SR-ARE: Safe
SR-ATAD5: Safe
SR-HSE: Safe
SR-MMP: Toxic
SR-p53: Toxic

General Properties

Boiling Point: 424.590
Hydration Free Energy: -2.900
Log(D) at pH=7.4: 3.500
Log(P): 2.77
Log S: -5.08
Log(Vapor Pressure): -9.29
Melting Point: 233.56
pKa Acid: 7.93
pKa Basic: 5.68

Protein Name	UniProt ID	Entry Name	Species	#Pharmacophore Points	Probability (0.7 ≤ Tversky Score ≤ 1.0)
Aldo-keto reductase family 1 member C2	P52895	AK1C2_HUMAN	Homo sapiens	3	0.9702
Aldo-keto reductase family 1 member C2	P52895	AK1C2_HUMAN	Homo sapiens	3	0.8997
Lactoylglutathione lyase	Q9CPU0	LGUL_MOUSE	Mus musculus	2	0.7597
Neocarzinostatin	P0A3R9	NCZS_STRCZ	Streptomyces carzinostaticus	3	0.7507

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