Tiamenone B - Compound Card

Tiamenone B

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Tiamenone B

Structure
Zoomed Structure
  • Family: Plantae - Meliaceae
  • Kingdom: Plantae
  • Class: Terpenoid
    • Subclass: Ergostane Steroid
Canonical Smiles C=C(C(C)C)CC[C@@]([C@H]1CC[C@@H]2[C@]1(C)CC[C@H]1[C@H]2CCC2=CC(=O)CC[C@]12C)(O)C
InChI InChI=1S/C28H44O2/c1-18(2)19(3)11-16-28(6,30)25-10-9-23-22-8-7-20-17-21(29)12-14-26(20,4)24(22)13-15-27(23,25)5/h17-18,22-25,30H,3,7-16H2,1-2,4-6H3/t22-,23-,24-,25-,26-,27-,28-/m0/s1
InChIKey IPPUVIIFVXVUFR-RMIXPHLWSA-N
Formula C28H44O2
HBA 2
HBD 1
MW 412.66
Rotatable Bonds 5
TPSA 37.3
LogP 6.88
Number Rings 4
Number Aromatic Rings 0
Heavy Atom Count 30
Formal Charge 0
Fraction CSP3 0.82
Exact Mass 412.33
Number of Lipinski Rule Violations 1
# Species Family Kingdom NCBI Taxonomy ID
1 Entandrophragma angolense Meliaceae Plantae 587577

Showing of synonyms

  • Happi GM, Wouamba SCN, et al. (2020). Ergostane-type steroids from the Cameroonian 'white tiama' Entandrophragma angolense.. Steroids,2020, 156, 108584. [View] [PubMed]
Pubchem: 122390694

No compound-protein relationship available.

Structure

SMILES: C1CCC(C12)CCC3C2CCC=4C3CCC(=O)C4

Level: 0

Mol. Weight: 412.66 g/mol

Antiviral

Absorption

Caco-2 (logPapp)
-4.73
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.45
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.88

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
1.82
Plasma Protein Binding
85.43
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
8.84
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
0.49
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.98
Liver Injury II
Toxic
hERG Blockers
Toxic
Daphnia Maga
6.31
Micronucleos
Safe
NR-AhR
Safe
NR-AR
Toxic
NR-AR-LBD
Toxic
NR-Aromatase
Safe
NR-ER
Safe
NR-ER-LBD
Safe
NR-GR
Toxic
NR-PPAR-gamma
Safe
NR-TR
Toxic
T. Pyriformis
-25.26
Rat (Acute)
2.56
Rat (Chronic Oral)
1.98
Fathead Minnow
3.92
Respiratory Disease
Toxic
Skin Sensitisation
Toxic
SR-ARE
Toxic
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Safe

General Properties

Boiling Point
428.36
Hydration Free Energy
-3.65
Log(D) at pH=7.4
5.62
Log(P)
6.17
Log S
-6.22
Log(Vapor Pressure)
-7.74
Melting Point
155.85
pKa Acid
11.77
pKa Basic
6.68
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.9467
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.9461
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.9343
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 3 0.9128
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.9066
Corticosteroid-binding globulin P08185 CBG_HUMAN Homo sapiens 3 0.8943
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8934
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 3 0.8928
Vitamin D(3) 25-hydroxylase C4B644 CPVDH_PSEAH Pseudonocardia autotrophica 3 0.8847
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.8714
Progesterone receptor P06401 PRGR_HUMAN Homo sapiens 4 0.8579
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.8538
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.8388
Retinol-binding protein 1 P02696 RET1_RAT Rattus norvegicus 3 0.8373
Progesterone receptor P06401 PRGR_HUMAN Homo sapiens 3 0.8367
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 4 0.8354
17-beta-hydroxysteroid dehydrogenase type 1 P14061 DHB1_HUMAN Homo sapiens 3 0.8306
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 4 0.8282
NPC intracellular cholesterol transporter 1 O15118 NPC1_HUMAN Homo sapiens 3 0.8215
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 4 0.8181
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 4 0.8168
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 4 0.8144
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 4 0.8139
Sex hormone-binding globulin P04278 SHBG_HUMAN Homo sapiens 3 0.8137
Beta-lactoglobulin P02754 LACB_BOVIN Bos taurus 3 0.8131
Progesterone receptor P06401 PRGR_HUMAN Homo sapiens 3 0.8122
Androgen receptor O97775 ANDR_PANTR Pan troglodytes 4 0.8061
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 4 0.8052
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8018
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 4 0.8011
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 4 0.7989
Androgen receptor O97775 ANDR_PANTR Pan troglodytes 4 0.7984
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 4 0.7959
Oxysterols receptor LXR-beta P55055 NR1H2_HUMAN Homo sapiens 4 0.7952
Androgen receptor O97775 ANDR_PANTR Pan troglodytes 4 0.7942
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 4 0.7939
Androgen receptor O97775 ANDR_PANTR Pan troglodytes 4 0.7937
Androgen receptor O97775 ANDR_PANTR Pan troglodytes 4 0.7905
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 4 0.7891
Androgen receptor O97775 ANDR_PANTR Pan troglodytes 4 0.7891
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.7886
Protein BRASSINOSTEROID INSENSITIVE 1 O22476 BRI1_ARATH Arabidopsis thaliana 3 0.7864
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 4 0.7861
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 4 0.7857
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 4 0.7853
Retinol dehydratase Q26490 Q26490_SPOFR Spodoptera frugiperda 3 0.7843
Mineralocorticoid receptor P08235 MCR_HUMAN Homo sapiens 3 0.7840
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 4 0.7831
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 4 0.7808
Protein BRASSINOSTEROID INSENSITIVE 1 O22476 BRI1_ARATH Arabidopsis thaliana 3 0.7799
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.7789
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 4 0.7761
Type IV / VI secretion system DotU domain-containing protein Q9KN50 Q9KN50_VIBCH Vibrio cholerae serotype O1 2 0.7758
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 4 0.7755
Sex hormone-binding globulin P04278 SHBG_HUMAN Homo sapiens 4 0.7755
Androgen receptor P19091 ANDR_MOUSE Mus musculus 4 0.7725
Protein BRASSINOSTEROID INSENSITIVE 1 O22476 BRI1_ARATH Arabidopsis thaliana 3 0.7704
Androgen receptor O97775 ANDR_PANTR Pan troglodytes 4 0.7688
Sex hormone-binding globulin P04278 SHBG_HUMAN Homo sapiens 3 0.7678
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 4 0.7668
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 4 0.7660
Androgen receptor O97775 ANDR_PANTR Pan troglodytes 4 0.7637
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 4 0.7624
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 4 0.7597
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 4 0.7578
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 4 0.7552
Beta-1 adrenergic receptor P07700 ADRB1_MELGA Meleagris gallopavo 3 0.7527
Beta-lactoglobulin P02754 LACB_BOVIN Bos taurus 3 0.7467
Lanosterol 14-alpha-demethylase Q385E8 Q385E8_TRYB2 Trypanosoma brucei brucei 3 0.7448
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 4 0.7431
Peptidyl-prolyl cis-trans isomerase FKBP1A P62942 FKB1A_HUMAN Homo sapiens 4 0.7326
Probable NDP-rhamnosyltransferase Q9ALM8 Q9ALM8_SACSN Saccharopolyspora spinosa 3 0.7302
Beta-1 adrenergic receptor P07700 ADRB1_MELGA Meleagris gallopavo 3 0.7248
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 2 0.7167
Steroid C26-monooxygenase P9WPP1 CP125_MYCTU Mycobacterium tuberculosis 3 0.7140
Mineralocorticoid receptor P08235 MCR_HUMAN Homo sapiens 3 0.7126
NPC intracellular cholesterol transporter 1 O15118 NPC1_HUMAN Homo sapiens 4 0.7074
Vitamin D3 receptor P13053 VDR_RAT Rattus norvegicus 3 0.7061
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7021

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