Sapelenin H - Compound Card

Sapelenin H

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Sapelenin H

Structure
Zoomed Structure
  • Family: Meliaceae
  • Kingdom: Plantae
  • Class: Terpenoid
    • Subclass: Acyclic Triterpenoid
Canonical Smiles C/C(=C\CC/C=C(/CC[C@@H]([C@@]1(C)CC[C@H](O1)C(O)(C)C)O)\C)/CC/C=C(/CCC1OC1(C)C)\C
InChI InChI=1S/C30H52O4/c1-22(14-11-15-24(3)17-19-27-29(6,7)33-27)12-9-10-13-23(2)16-18-25(31)30(8)21-20-26(34-30)28(4,5)32/h12-13,15,25-27,31-32H,9-11,14,16-21H2,1-8H3/b22-12+,23-13+,24-15+/t25-,26-,27?,30+/m0/s1
InChIKey DJKSJAZDBWRFLH-VEHOLORFSA-N
Formula C30H52O4
HBA 4
HBD 2
MW 476.74
Rotatable Bonds 14
TPSA 62.22
LogP 7.19
Number Rings 2
Number Aromatic Rings 0
Heavy Atom Count 34
Formal Charge 0
Fraction CSP3 0.8
Exact Mass 476.39
Number of Lipinski Rule Violations 1
# Species Family Kingdom NCBI Taxonomy ID
1 Entandrophragma cylindricum Meliaceae Plantae 179994

Showing of synonyms

  • Kouam SF, Kusari S, et al. (2012). Sapelenins G-J, acyclic triterpenoids with strong anti-inflammatory activities from the bark of the Cameroonian medicinal plant Entandrophragma cylindricum.. Phytochemistry,2012, 83, 79-86. [View] [PubMed]
Pubchem: 71500884

No compound-protein relationship available.

Structure

SMILES: O1CC1CCC=CCCC=CCCC=CCCCC2CCCO2

Level: 1

Mol. Weight: 318.5 g/mol

Structure

SMILES: C1CCOC1

Level: 0

Mol. Weight: 72.11 g/mol

Structure

SMILES: C1CO1

Level: 0

Mol. Weight: 44.05 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-5.04
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.78
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Inhibitor
P-Glycoprotein Substrate
Substrate
Skin Permeability
-3.53

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.85
Plasma Protein Binding
55.23
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
6.85
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
2.21
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.12
Liver Injury II
Safe
hERG Blockers
Safe
Daphnia Maga
6.8
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
-78.81
Rat (Acute)
2.33
Rat (Chronic Oral)
1.98
Fathead Minnow
5.91
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
448.89
Hydration Free Energy
-2.94
Log(D) at pH=7.4
4.46
Log(P)
6.68
Log S
-5.8
Log(Vapor Pressure)
-6.85
Melting Point
19.25
pKa Acid
8.93
pKa Basic
5.17
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 0.9728
Rhodopsin P02699 OPSD_BOVIN Bos taurus 3 0.9468
Methylketone synthase I E0YCS2 E0YCS2_SOLHA Solanum habrochaites 3 0.9455
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 3 0.9451
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.9378
Corticosteroid-binding globulin P08185 CBG_HUMAN Homo sapiens 3 0.9233
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 3 0.9222
Beta-lactoglobulin P02754 LACB_BOVIN Bos taurus 3 0.9188
Prolyl tripeptidyl peptidase Q7MUW6 PTP_PORGI Porphyromonas gingivalis 3 0.9176
Neocarzinostatin P0A3R9 NCZS_STRCZ Streptomyces carzinostaticus 3 0.9146
Retinol-binding protein 2 P50120 RET2_HUMAN Homo sapiens 3 0.9125
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.9035
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 4 0.9026
Beta-lactoglobulin P02754 LACB_BOVIN Bos taurus 3 0.8988
Trichothecene 15-O-acetyltransferase TRI3 Q9C1B7 TRI3_FUSSP Fusarium sporotrichioides 3 0.8950
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.8905
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.8896
Retinol dehydratase Q26490 Q26490_SPOFR Spodoptera frugiperda 3 0.8762
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.8761
Cytochrome P450 monooxygenase Q5YNS8 Q5YNS8_NOCFA Nocardia farcinica 3 0.8634
Probable NDP-rhamnosyltransferase Q9ALM8 Q9ALM8_SACSN Saccharopolyspora spinosa 3 0.8600
Vitamin D(3) 25-hydroxylase C4B644 CPVDH_PSEAH Pseudonocardia autotrophica 3 0.8597
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 3 0.8530
Sex hormone-binding globulin P04278 SHBG_HUMAN Homo sapiens 3 0.8527
Vitamin D3 receptor P13053 VDR_RAT Rattus norvegicus 3 0.8524
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.8496
Cytochrome P450 monooxygenase Q5YNS8 Q5YNS8_NOCFA Nocardia farcinica 3 0.8472
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.8425
Aldo-keto reductase family 1 member C3 P42330 AK1C3_HUMAN Homo sapiens 3 0.8396
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.8387
Bacteriorhodopsin P02945 BACR_HALSA Halobacterium salinarum 3 0.8360
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8347
Cholesterol side-chain cleavage enzyme, mitochondrial P05108 CP11A_HUMAN Homo sapiens 3 0.8328
Soluble cytochrome b562 P0ABE7 C562_ECOLX Escherichia coli 4 0.8279
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 3 0.8211
Protein BRASSINOSTEROID INSENSITIVE 1 O22476 BRI1_ARATH Arabidopsis thaliana 4 0.8149
Hemolymph juvenile hormone binding protein Q9U556 Q9U556_BOMMO Bombyx mori 3 0.8132
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.8107
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.8093
Nuclear receptor ROR-gamma P51449 RORG_HUMAN Homo sapiens 3 0.8088
Sulfotransferase 2B1 O00204 ST2B1_HUMAN Homo sapiens 2 0.8069
Retinaldehyde-binding protein 1 P12271 RLBP1_HUMAN Homo sapiens 3 0.8034
Peptidyl-prolyl cis-trans isomerase FKBP1A P62942 FKB1A_HUMAN Homo sapiens 4 0.7988
Japanin M1MR49 M1MR49_RHIAP Rhipicephalus appendiculatus 3 0.7981
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7941
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7935
Nuclear receptor ROR-alpha P35398 RORA_HUMAN Homo sapiens 3 0.7921
Acetylcholinesterase P04058 ACES_TETCF Tetronarce californica 3 0.7917
Beta-lactoglobulin P02754 LACB_BOVIN Bos taurus 3 0.7889
Retinol-binding protein 2 P06768 RET2_RAT Rattus norvegicus 3 0.7882
Retinol-binding protein 1 P09455 RET1_HUMAN Homo sapiens 3 0.7875
11-beta-hydroxysteroid dehydrogenase 1 P50172 DHI1_MOUSE Mus musculus 3 0.7868
Retinol-binding protein 1 P02696 RET1_RAT Rattus norvegicus 3 0.7867
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 3 0.7852
Acetylcholinesterase P21836 ACES_MOUSE Mus musculus 3 0.7823
3-ketosteroid dehydrogenase Q9RA02 Q9RA02_RHOER Rhodococcus erythropolis 2 0.7817
Sulfotransferase 2A1 Q06520 ST2A1_HUMAN Homo sapiens 3 0.7810
Abscisic acid receptor PYL10 Q8H1R0 PYL10_ARATH Arabidopsis thaliana 3 0.7801
Nuclear receptor coactivator 2 Q15596 NCOA2_HUMAN Homo sapiens 3 0.7789
Retinoic acid receptor RXR Q8T5C6 RXR_BIOGL Biomphalaria glabrata 3 0.7772
Lanosterol synthase P48449 ERG7_HUMAN Homo sapiens 3 0.7765
NPC intracellular cholesterol transporter 1 O15118 NPC1_HUMAN Homo sapiens 3 0.7756
Nuclear receptor ROR-gamma P51449 RORG_HUMAN Homo sapiens 2 0.7721
Integrin alpha-L P20701 ITAL_HUMAN Homo sapiens 3 0.7718
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7709
Protein BRASSINOSTEROID INSENSITIVE 1 O22476 BRI1_ARATH Arabidopsis thaliana 4 0.7704
Lanosterol 14-alpha-demethylase Q385E8 Q385E8_TRYB2 Trypanosoma brucei brucei 3 0.7689
Phospholipase A2, major isoenzyme P00592 PA21B_PIG Sus scrofa 4 0.7685
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.7667
Gastrotropin P51161 FABP6_HUMAN Homo sapiens 3 0.7658
Beta-1 adrenergic receptor P07700 ADRB1_MELGA Meleagris gallopavo 3 0.7648
Retinaldehyde-binding protein 1 P12271 RLBP1_HUMAN Homo sapiens 3 0.7642
Putative cytochrome P450 120 Q59990 CP120_SYNY3 Synechocystis sp 3 0.7628
Retinol-binding protein 4 P18902 RET4_BOVIN Bos taurus 3 0.7624
Chloramphenicol acetyltransferase P62577 CAT_ECOLX Escherichia coli 4 0.7620
Soluble cytochrome b562 P0ABE7 C562_ECOLX Escherichia coli 3 0.7611
Cellular retinol-binding protein type II Q8UVG6 Q8UVG6_DANRE Danio rerio 3 0.7590
Beta-1 adrenergic receptor P07700 ADRB1_MELGA Meleagris gallopavo 2 0.7578
17-beta-hydroxysteroid dehydrogenase type 1 P14061 DHB1_HUMAN Homo sapiens 3 0.7571
ADP-ribosylation factor 1 P84077 ARF1_HUMAN Homo sapiens 2 0.7567
Retinol-binding protein 4 P18902 RET4_BOVIN Bos taurus 3 0.7552
Fatty acid-binding protein, liver P80226 FABPL_CHICK Gallus gallus 2 0.7551
Progesterone receptor P06401 PRGR_HUMAN Homo sapiens 3 0.7541
Phospholipase A2, major isoenzyme P00592 PA21B_PIG Sus scrofa 3 0.7535
NPC intracellular cholesterol transporter 1 O15118 NPC1_HUMAN Homo sapiens 2 0.7530
Bile acid receptor Q62735 NR1H4_RAT Rattus norvegicus 4 0.7526
Multidrug transporter MdfA P0AEY8 MDFA_ECOLI Escherichia coli 3 0.7518
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 2 0.7512
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 3 0.7504
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7473
Sulfotransferase 2B1 O00204 ST2B1_HUMAN Homo sapiens 3 0.7466
Cartilage oligomeric matrix protein P35444 COMP_RAT Rattus norvegicus 3 0.7453
Peptidyl-prolyl cis-trans isomerase FKBP1A P62942 FKB1A_HUMAN Homo sapiens 3 0.7447
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7447
Protein BRASSINOSTEROID INSENSITIVE 1 O22476 BRI1_ARATH Arabidopsis thaliana 4 0.7444
Abscisic acid receptor PYL2 O80992 PYL2_ARATH Arabidopsis thaliana 2 0.7432
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7425
Gastrotropin Q6IMW5 Q6IMW5_DANRE Danio rerio 3 0.7413
Nuclear receptor subfamily 1 group I member 3 O35627 NR1I3_MOUSE Mus musculus 3 0.7402
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7400
Beta-1 adrenergic receptor P07700 ADRB1_MELGA Meleagris gallopavo 3 0.7399
4,4'-diapophytoene synthase A9JQL9 CRTM_STAAU Staphylococcus aureus 2 0.7383
17-beta-hydroxysteroid dehydrogenase type 1 P14061 DHB1_HUMAN Homo sapiens 3 0.7372
Fatty acid-binding protein, liver P80226 FABPL_CHICK Gallus gallus 2 0.7363
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 3 0.7350
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7345
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 2 0.7334
Methionine aminopeptidase 2 P9WK19 MAP12_MYCTU Mycobacterium tuberculosis 3 0.7272
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 2 0.7269
Sex hormone-binding globulin P04278 SHBG_HUMAN Homo sapiens 3 0.7267
Sodium-dependent dopamine transporter Q7K4Y6 DAT_DROME Drosophila melanogaster 2 0.7253
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7252
Retinol-binding protein 1 P09455 RET1_HUMAN Homo sapiens 3 0.7250
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7249
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 2 0.7244
Abscisic acid receptor PYL3 Q9SSM7 PYL3_ARATH Arabidopsis thaliana 2 0.7240
Phospholipase A2, major isoenzyme P00592 PA21B_PIG Sus scrofa 3 0.7229
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.7219
Vitamin D3 receptor P13053 VDR_RAT Rattus norvegicus 3 0.7214
Retinol-binding protein 2 P06768 RET2_RAT Rattus norvegicus 3 0.7212
3-alpha-hydroxysteroid dehydrogenase P23457 DIDH_RAT Rattus norvegicus 2 0.7192
Steroid C26-monooxygenase P9WPP1 CP125_MYCTU Mycobacterium tuberculosis 3 0.7188
Retinol-binding protein 4 P18902 RET4_BOVIN Bos taurus 3 0.7156
Gibberellin receptor GID1 Q6L545 GID1_ORYSJ Oryza sativa subsp. japonica 3 0.7150
Gibberellin receptor GID1A Q9MAA7 GID1A_ARATH Arabidopsis thaliana 3 0.7145
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 3 0.7142
Type IV / VI secretion system DotU domain-containing protein Q9KN50 Q9KN50_VIBCH Vibrio cholerae serotype O1 2 0.7128
Beta-1 adrenergic receptor P07700 ADRB1_MELGA Meleagris gallopavo 3 0.7113
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7108
Corticosteroid-binding globulin P31211 CBG_RAT Rattus norvegicus 3 0.7107
Vitamin D3 dihydroxylase P18326 CPXE_STRGO Streptomyces griseolus 3 0.7104
Beta-1 adrenergic receptor P07700 ADRB1_MELGA Meleagris gallopavo 2 0.7103
Cellular retinoic acid-binding protein 2 P29373 RABP2_HUMAN Homo sapiens 2 0.7102
Steroid 17-alpha-hydroxylase/17,20 lyase P05093 CP17A_HUMAN Homo sapiens 3 0.7089
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7087
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7066
Carnitine O-acetyltransferase P47934 CACP_MOUSE Mus musculus 2 0.7066
Vitamin D3 receptor P13053 VDR_RAT Rattus norvegicus 3 0.7058
ADP-ribosylation factor 1 P84080 ARF1_BOVIN Bos taurus 3 0.7057
Angiotensin-converting enzyme Q10714 ACE_DROME Drosophila melanogaster 3 0.7049
Vitamin D 25-hydroxylase Q6VVX0 CP2R1_HUMAN Homo sapiens 3 0.7048
Nuclear receptor subfamily 1 group I member 2 O75469 NR1I2_HUMAN Homo sapiens 3 0.7048
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7030
Beta-1 adrenergic receptor P07700 ADRB1_MELGA Meleagris gallopavo 3 0.7023
Phospholipase A2, major isoenzyme P00592 PA21B_PIG Sus scrofa 2 0.7008

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