Hellebrigenin 3,5-diacetate - Compound Card

Hellebrigenin 3,5-diacetate

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Hellebrigenin 3,5-diacetate

Structure
Zoomed Structure
  • Family: Plantae - Melianthaceae
  • Kingdom: Plantae
  • Class: Steroid
Canonical Smiles O=C[C@@]12CC[C@@H](C[C@]2(CC[C@@H]2[C@@H]1CC[C@]1([C@]2(O)CC[C@@H]1c1ccc(=O)oc1)C)OC(=O)C)OC(=O)C
InChI InChI=1S/C28H36O8/c1-17(30)35-20-6-11-26(16-29)22-7-10-25(3)21(19-4-5-24(32)34-15-19)9-13-28(25,33)23(22)8-12-27(26,14-20)36-18(2)31/h4-5,15-16,20-23,33H,6-14H2,1-3H3/t20-,21+,22-,23+,25+,26-,27-,28-/m0/s1
InChIKey CCZLIPXVLKAJFW-GBGREZBSSA-N
Formula C28H36O8
HBA 8
HBD 1
MW 500.59
Rotatable Bonds 4
TPSA 120.11
LogP 3.68
Number Rings 5
Number Aromatic Rings 1
Heavy Atom Count 36
Formal Charge 0
Fraction CSP3 0.71
Exact Mass 500.24
Number of Lipinski Rule Violations 1
# Species Family Kingdom NCBI Taxonomy ID
1 Bersama abyssinica Melianthaceae Plantae 113247
2 Bersama abyssinica Melianthaceae Plantae 113247

Showing of synonyms

  • Kupchan SM, Hemingway RJ, et al. (1968). The isolation and characterization of hellebrigenin 3-acetate and hellebrigenin 3, 5-diacetate, bufadienolide tumor inhibitors from Bersama abyssinica.. Tetrahedron letters,1968,9(2),149-152. [View] [PubMed]
  • Kupchan SM, Hemingway RJ, et al. (1969). XLIV. Isolation and characterization of hellebrigenin 3-acetate and hellebrigenin 3, 5-diacetate, Bufadienolide tumor inhibitors from Bersama abyssinica.. The Journal of organic chemistry,1969,34(12),3894-3898. [View] [PubMed]
Pubchem: 268867

No compound-protein relationship available.

Structure

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

Level: 1

Mol. Weight: 500.59 g/mol

Structure

SMILES: C1CCC(C12)CCC3C2CCC4C3CCCC4

Level: 0

Mol. Weight: 500.59 g/mol

Structure

SMILES: O=c1cccco1

Level: 0

Mol. Weight: 500.59 g/mol

Cytotoxic

Absorption

Caco-2 (logPapp)
-4.82
Human Oral Bioavailability 20%
Non-Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.73
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-1.73

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.66
Plasma Protein Binding
69.9
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
Non-Substrate
OATP1B1
Non-Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
7.2
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-1.11
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
-0.02
Liver Injury II
Toxic
hERG Blockers
Toxic
Daphnia Maga
6.66
Micronucleos
Toxic
NR-AhR
Safe
NR-AR
Toxic
NR-AR-LBD
Toxic
NR-Aromatase
Safe
NR-ER
Toxic
NR-ER-LBD
Safe
NR-GR
Toxic
NR-PPAR-gamma
Safe
NR-TR
Safe
T. Pyriformis
-560.33
Rat (Acute)
5.32
Rat (Chronic Oral)
1.32
Fathead Minnow
4.01
Respiratory Disease
Safe
Skin Sensitisation
Safe
SR-ARE
Safe
SR-ATAD5
Toxic
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Safe

General Properties

Boiling Point
481.31
Hydration Free Energy
-2.97
Log(D) at pH=7.4
2.31
Log(P)
2.27
Log S
-4.68
Log(Vapor Pressure)
-9.19
Melting Point
227.39
pKa Acid
7.78
pKa Basic
5.47
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.9739
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.9739
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.8744
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.8744
Pantothenate synthetase P9WIL5 PANC_MYCTU Mycobacterium tuberculosis 3 0.8231
Pantothenate synthetase P9WIL5 PANC_MYCTU Mycobacterium tuberculosis 3 0.8231
High affinity 3',5'-cyclic-AMP phosphodiesterase 7A Q13946 PDE7A_HUMAN Homo sapiens 3 0.7976
High affinity 3',5'-cyclic-AMP phosphodiesterase 7A Q13946 PDE7A_HUMAN Homo sapiens 3 0.7976
Norsolorinic acid synthase Q12053 AFLC_ASPPU Aspergillus parasiticus 3 0.7861
Norsolorinic acid synthase Q12053 AFLC_ASPPU Aspergillus parasiticus 3 0.7861
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 3 0.7858
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 3 0.7858
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7821
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7821
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase Q05603 COBT_SALTY Salmonella typhimurium 2 0.7613
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase Q05603 COBT_SALTY Salmonella typhimurium 2 0.7613
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 3 0.7556
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 3 0.7556
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 3 0.7495
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 3 0.7495
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7469
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7469
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7461
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7461
Polymerase acidic protein C3W5S0 C3W5S0_I09A0 Influenza A virus 2 0.7459
Polymerase acidic protein C3W5S0 C3W5S0_I09A0 Influenza A virus 2 0.7459
cGMP-dependent 3',5'-cyclic phosphodiesterase O00408 PDE2A_HUMAN Homo sapiens 2 0.7430
cGMP-dependent 3',5'-cyclic phosphodiesterase O00408 PDE2A_HUMAN Homo sapiens 2 0.7430
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 3 0.7392
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 3 0.7392
LIM domain kinase 1 P53667 LIMK1_HUMAN Homo sapiens 2 0.7386
LIM domain kinase 1 P53667 LIMK1_HUMAN Homo sapiens 2 0.7386
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 2 0.7341
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 2 0.7341
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 2 0.7324
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 2 0.7324
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 2 0.7294
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 2 0.7294
Beta-galactoside-specific lectin 4 Q6ITZ3 ML4_VISAL Viscum album 2 0.7255
Beta-galactoside-specific lectin 4 Q6ITZ3 ML4_VISAL Viscum album 2 0.7255
Ribosomal small subunit pseudouridine synthase A P0AA43 RSUA_ECOLI Escherichia coli 2 0.7247
Ribosomal small subunit pseudouridine synthase A P0AA43 RSUA_ECOLI Escherichia coli 2 0.7247
Pheromone-binding protein ASP1 Q9U9J6 Q9U9J6_APIME Apis mellifera 3 0.7158
Pheromone-binding protein ASP1 Q9U9J6 Q9U9J6_APIME Apis mellifera 3 0.7158
5'-methylthioadenosine/S-adenosylhomocysteine nucleosidase Q81LL4 MTNN_BACAN Bacillus anthracis 2 0.7142
5'-methylthioadenosine/S-adenosylhomocysteine nucleosidase Q81LL4 MTNN_BACAN Bacillus anthracis 2 0.7142
Avidin P02701 AVID_CHICK Gallus gallus 2 0.7120
Avidin P02701 AVID_CHICK Gallus gallus 2 0.7120
Bifunctional epoxide hydrolase 2 P34913 HYES_HUMAN Homo sapiens 2 0.7113
Bifunctional epoxide hydrolase 2 P34913 HYES_HUMAN Homo sapiens 2 0.7113
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 2 0.7110
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 2 0.7110
cGMP-specific 3',5'-cyclic phosphodiesterase O76074 PDE5A_HUMAN Homo sapiens 3 0.7103
cGMP-specific 3',5'-cyclic phosphodiesterase O76074 PDE5A_HUMAN Homo sapiens 3 0.7103

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