3beta,16beta-dihydroxy-5beta-bufa-20,22-dienolide - Compound Card

3beta,16beta-dihydroxy-5beta-bufa-20,22-dienolide

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3beta,16beta-dihydroxy-5beta-bufa-20,22-dienolide

Structure
Zoomed Structure
  • Family: Plantae - Hyacinthaceae
  • Kingdom: Plantae
  • Class: Steroid
    • Subclass: Bufadienolide
Canonical Smiles O[C@H]1CC[C@]2([C@@H](C1)CC[C@@H]1[C@@H]2CC[C@]2([C@@H]1C[C@@H]([C@@H]2c1ccc(=O)oc1)O)C)C
InChI InChI=1S/C24H34O4/c1-23-9-7-16(25)11-15(23)4-5-17-18(23)8-10-24(2)19(17)12-20(26)22(24)14-3-6-21(27)28-13-14/h3,6,13,15-20,22,25-26H,4-5,7-12H2,1-2H3/t15-,16+,17-,18+,19-,20+,22+,23+,24+/m1/s1
InChIKey LOQBMALJVSKCDP-CQIAZTITSA-N
Formula C24H34O4
HBA 4
HBD 2
MW 386.53
Rotatable Bonds 1
TPSA 70.67
LogP 4.1
Number Rings 5
Number Aromatic Rings 1
Heavy Atom Count 28
Formal Charge 0
Fraction CSP3 0.79
Exact Mass 386.25
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Drimia depressa Hyacinthaceae Plantae 65772

Showing of synonyms

  • Crouch NR, Langlois A, et al. (2007). Bufadienolides from the southern African Drimia depressa (Hyacinthaceae: Urgineoideae). Phytochemistry, 2007, 68(13), 1731–1734. [View]
Pubchem: 102321429
Nmrshiftdb2: 70085400

No compound-protein relationship available.

Structure

SMILES: C1CCCC(CC2)C1C(CC3)C2C(C34)CCC4c5ccc(=O)oc5

Level: 1

Mol. Weight: 386.53 g/mol

Structure

SMILES: C1CCC(C12)CCC3C2CCC4C3CCCC4

Level: 0

Mol. Weight: 386.53 g/mol

Structure

SMILES: O=c1cccco1

Level: 0

Mol. Weight: 386.53 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.77
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.26
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.9

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.97
Plasma Protein Binding
81.56
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
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
11.21
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-0.59
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.0
Liver Injury II
Toxic
hERG Blockers
Toxic
Daphnia Maga
5.49
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
Safe
T. Pyriformis
-18.66
Rat (Acute)
3.5
Rat (Chronic Oral)
1.73
Fathead Minnow
3.92
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
465.63
Hydration Free Energy
-3.77
Log(D) at pH=7.4
3.81
Log(P)
3.61
Log S
-4.84
Log(Vapor Pressure)
-8.7
Melting Point
230.99
pKa Acid
8.63
pKa Basic
7.39
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 3 0.9327
3-alpha-hydroxysteroid dehydrogenase P23457 DIDH_RAT Rattus norvegicus 3 0.9175
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.9166
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8925
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8835
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8482
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.8453
Rhodopsin P02699 OPSD_BOVIN Bos taurus 3 0.8306
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 3 0.8298
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 3 0.8213
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8167
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.8107
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8095
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 3 0.8007
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.7997
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 3 0.7927
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.7918
Gastrotropin Q6IMW5 Q6IMW5_DANRE Danio rerio 3 0.7905
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7897
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 3 0.7767
High affinity 3',5'-cyclic-AMP phosphodiesterase 7A Q13946 PDE7A_HUMAN Homo sapiens 3 0.7685
Sulfide-quinone reductase B7JBP8 SQRD_ACIF2 Acidithiobacillus ferrooxidans) 3 0.7549
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase Q05603 COBT_SALTY Salmonella typhimurium 2 0.7538
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.7533
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 2 0.7434
Mitochondrial poly(A) polymerase F1NBW0 F1NBW0_CHICK Gallus gallus 2 0.7359
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 2 0.7355
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7351
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 2 0.7330
Polymerase acidic protein C3W5S0 C3W5S0_I09A0 Influenza A virus 2 0.7329
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7313
Beta-galactoside-specific lectin 4 Q6ITZ3 ML4_VISAL Viscum album 2 0.7293
Norsolorinic acid synthase Q12053 AFLC_ASPPU Aspergillus parasiticus 3 0.7281
Bilin-binding protein P09464 BBP_PIEBR Pieris brassicae 4 0.7275
17-beta-hydroxysteroid dehydrogenase 14 Q9BPX1 DHB14_HUMAN Homo sapiens 2 0.7232
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7207
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 4 0.7195
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7176
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7151
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7131
cGMP-dependent 3',5'-cyclic phosphodiesterase O00408 PDE2A_HUMAN Homo sapiens 2 0.7108
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 2 0.7081
5-methyltetrahydropteroyltriglutamate--homocysteine methyltransferase 1 O50008 METE1_ARATH Arabidopsis thaliana 2 0.7078
ActVA 6 protein Q53908 Q53908_STRCH Streptomyces coelicolor 3 0.7060
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7045

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