Turraeanin F - Compound Card

Turraeanin F

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Turraeanin F

Structure
Zoomed Structure
  • Family: Plantae - Meliaceae
  • Kingdom: Plantae
  • Class: Steroid
    • Subclass: Pregnane Steroid
Canonical Smiles OC[C@]1(C)CCC[C@@]2([C@@H]1CCC(=C)[C@H]2C/C=C/1\COCC1)C
InChI InChI=1S/C20H32O2/c1-15-5-8-18-19(2,14-21)10-4-11-20(18,3)17(15)7-6-16-9-12-22-13-16/h6,17-18,21H,1,4-5,7-14H2,2-3H3/b16-6-/t17-,18-,19+,20+/m1/s1
InChIKey YSZDIVGECYPNEY-WOTLCARSSA-N
Formula C20H32O2
HBA 2
HBD 1
MW 304.47
Rotatable Bonds 3
TPSA 29.46
LogP 4.49
Number Rings 3
Number Aromatic Rings 0
Heavy Atom Count 22
Formal Charge 0
Fraction CSP3 0.8
Exact Mass 304.24
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Turraeanthus africanus Meliaceae Plantae 1672009

Showing of synonyms

  • Chenda LBN, Kouam SF, et al. (2014). Isolation and characterization of six labdane diterpenes and one pregnane steroid of Turraeanthus africanus.. Phytochemistry,2014, 103, 137-144. [View] [PubMed]
Pubchem: 102125210

No compound-protein relationship available.

Structure

SMILES: C1OCCC1=CCC2C(=C)CCC(C23)CCCC3

Level: 1

Mol. Weight: 304.47 g/mol

Structure

SMILES: C=C(C1)CCC(C12)CCCC2

Level: 0

Mol. Weight: 304.47 g/mol

Structure

SMILES: C=C1CCOC1

Level: 0

Mol. Weight: 304.47 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.71
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.45
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-3.25

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
1.03
Plasma Protein Binding
64.89
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
Inhibitor
CYP 2C19 Substrate
Substrate
CYP 2C9 Inhibitor
Inhibitor
CYP 2C9 Substrate
Non-Substrate
CYP 2D6 Inhibitor
Non-Inhibitor
CYP 2D6 Substrate
Substrate
CYP 3A4 Inhibitor
Inhibitor
CYP 3A4 Substrate
Non-Substrate
OATP1B1
Non-Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
14.15
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
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
-1.96
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
4.7
Micronucleos
Safe
NR-AhR
Safe
NR-AR
Safe
NR-AR-LBD
Safe
NR-Aromatase
Safe
NR-ER
Safe
NR-ER-LBD
Safe
NR-GR
Safe
NR-PPAR-gamma
Safe
NR-TR
Safe
T. Pyriformis
-0.03
Rat (Acute)
2.63
Rat (Chronic Oral)
1.72
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
349.15
Hydration Free Energy
-3.42
Log(D) at pH=7.4
3.61
Log(P)
4.3
Log S
-4.95
Log(Vapor Pressure)
-6.09
Melting Point
84.74
pKa Acid
11.85
pKa Basic
7.49
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Retinol-binding protein 1 P02696 RET1_RAT Rattus norvegicus 3 0.8969
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 3 0.8946
Vitamin D(3) 25-hydroxylase C4B644 CPVDH_PSEAH Pseudonocardia autotrophica 3 0.8913
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 3 0.8783
Beta-lactoglobulin P02754 LACB_BOVIN Bos taurus 3 0.8677
Probable NDP-rhamnosyltransferase Q9ALM8 Q9ALM8_SACSN Saccharopolyspora spinosa 3 0.8527
Beta-lactoglobulin P02754 LACB_BOVIN Bos taurus 3 0.8447
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 3 0.8295
Cellular retinol-binding protein type II Q8UVG6 Q8UVG6_DANRE Danio rerio 3 0.8143
Lanosterol 14-alpha-demethylase Q385E8 Q385E8_TRYB2 Trypanosoma brucei brucei 3 0.8045
3-ketosteroid dehydrogenase Q9RA02 Q9RA02_RHOER Rhodococcus erythropolis 2 0.7994
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7949
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 2 0.7885
Epoxide hydrolase Q41415 Q41415_SOLTU Solanum tuberosum 3 0.7853
Retinol dehydratase Q26490 Q26490_SPOFR Spodoptera frugiperda 3 0.7848
Retinol-binding protein 2 P50120 RET2_HUMAN Homo sapiens 3 0.7814
Retinol-binding protein 1 P09455 RET1_HUMAN Homo sapiens 3 0.7808
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 3 0.7804
11-beta-hydroxysteroid dehydrogenase 1 P50172 DHI1_MOUSE Mus musculus 3 0.7803
Phospholipase A2, major isoenzyme P00592 PA21B_PIG Sus scrofa 3 0.7781
Aldo-keto reductase family 1 member C1 Q04828 AK1C1_HUMAN Homo sapiens 2 0.7682
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.7678
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 2 0.7566
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7565
NPC intracellular cholesterol transporter 1 O15118 NPC1_HUMAN Homo sapiens 2 0.7550
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 2 0.7529
Abscisic acid receptor PYL3 Q9SSM7 PYL3_ARATH Arabidopsis thaliana 2 0.7527
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 2 0.7524
Retinol-binding protein 2 P06768 RET2_RAT Rattus norvegicus 3 0.7487
17-beta-hydroxysteroid dehydrogenase type 1 P14061 DHB1_HUMAN Homo sapiens 3 0.7475
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7472
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 3 0.7461
Methylketone synthase I E0YCS2 E0YCS2_SOLHA Solanum habrochaites 2 0.7429
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 3 0.7399
NPC intracellular cholesterol transporter 1 O15118 NPC1_HUMAN Homo sapiens 3 0.7389
Cellular retinoic acid-binding protein 2 P29373 RABP2_HUMAN Homo sapiens 2 0.7386
Fatty acid-binding protein 10-A, liver basic Q9I8L5 FA10A_DANRE Danio rerio 2 0.7376
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7376
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 3 0.7373
Sulfotransferase 2A1 Q06520 ST2A1_HUMAN Homo sapiens 2 0.7362
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.7346
Vitamin D-binding protein P02774 VTDB_HUMAN Homo sapiens 2 0.7316
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 2 0.7312
Lanosterol synthase P48449 ERG7_HUMAN Homo sapiens 3 0.7293
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 2 0.7263
Sulfotransferase 2A1 Q06520 ST2A1_HUMAN Homo sapiens 2 0.7261
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7234
Type IV / VI secretion system DotU domain-containing protein Q9KN50 Q9KN50_VIBCH Vibrio cholerae serotype O1 2 0.7168
Retinaldehyde-binding protein 1 P12271 RLBP1_HUMAN Homo sapiens 3 0.7149
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7122
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7120
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7100
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 2 0.7092
Steroid 17-alpha-hydroxylase/17,20 lyase P05093 CP17A_HUMAN Homo sapiens 2 0.7082
Progesterone receptor P06401 PRGR_HUMAN Homo sapiens 2 0.7078
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 3 0.7078
Retinol-binding protein 2 P50120 RET2_HUMAN Homo sapiens 3 0.7065
Nuclear receptor ROR-gamma P51449 RORG_HUMAN Homo sapiens 2 0.7058
Beta-1 adrenergic receptor P07700 ADRB1_MELGA Meleagris gallopavo 3 0.7050
Progesterone receptor P06401 PRGR_HUMAN Homo sapiens 2 0.7040
Beta-elicitin cryptogein P15570 ELIB_PHYCR Phytophthora cryptogea 3 0.7034

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