Sapelenin I - Compound Card

Sapelenin I

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Sapelenin I

Structure
Zoomed Structure
  • Family: Plantae - Meliaceae
  • Kingdom: Plantae
  • Class: Terpenoid
    • Subclass: Acyclic Triterpenoid
Canonical Smiles C/C(=C\CCC(C(CC[C@@H]([C@@]1(C)CC[C@H](O1)C(O)(C)C)O)(O)C)O)/CC/C=C(/CCC=C(C)C)\C
InChI InChI=1S/C30H54O5/c1-22(2)12-9-13-23(3)14-10-15-24(4)16-11-17-25(31)29(7,34)20-18-26(32)30(8)21-19-27(35-30)28(5,6)33/h12,14,16,25-27,31-34H,9-11,13,15,17-21H2,1-8H3/b23-14+,24-16+/t25?,26-,27-,29?,30+/m0/s1
InChIKey BJJSTHFFAHQGAA-JMKXVNJXSA-N
Formula C30H54O5
HBA 5
HBD 4
MW 494.76
Rotatable Bonds 15
TPSA 90.15
LogP 6.15
Number Rings 1
Number Aromatic Rings 0
Heavy Atom Count 35
Formal Charge 0
Fraction CSP3 0.8
Exact Mass 494.4
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: 71501069

No compound-protein relationship available.

Structure

SMILES: C1CCOC1

Level: 0

Mol. Weight: 494.76 g/mol

High potency in suppressing the secretion of il-17

Absorption

Caco-2 (logPapp)
-4.99
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.95
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Inhibitor
P-Glycoprotein Substrate
Substrate
Skin Permeability
-2.51

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
1.04
Plasma Protein Binding
60.33
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
Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
0.31
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
0.45
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
-0.67
Liver Injury II
Safe
hERG Blockers
Safe
Daphnia Maga
6.02
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
-87.83
Rat (Acute)
2.26
Rat (Chronic Oral)
2.26
Fathead Minnow
5.01
Respiratory Disease
Toxic
Skin Sensitisation
Toxic
SR-ARE
Safe
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Toxic
SR-p53
Safe

General Properties

Boiling Point
454.53
Hydration Free Energy
-3.35
Log(D) at pH=7.4
3.82
Log(P)
6.34
Log S
-4.79
Log(Vapor Pressure)
-7.88
Melting Point
55.92
pKa Acid
9.54
pKa Basic
6.61
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Beta-lactoglobulin P02754 LACB_BOVIN Bos taurus 3 0.9316
Rhodopsin P02699 OPSD_BOVIN Bos taurus 3 0.9174
Neocarzinostatin P0A3R9 NCZS_STRCZ Streptomyces carzinostaticus 3 0.9109
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 3 0.8977
Beta-lactoglobulin P02754 LACB_BOVIN Bos taurus 3 0.8893
Probable NDP-rhamnosyltransferase Q9ALM8 Q9ALM8_SACSN Saccharopolyspora spinosa 3 0.8771
Beta-lactoglobulin P02754 LACB_BOVIN Bos taurus 3 0.8641
Prolyl tripeptidyl peptidase Q7MUW6 PTP_PORGI Porphyromonas gingivalis 3 0.8571
Serpin domain-containing protein H0ZQY2 H0ZQY2_TAEGU Taeniopygia guttata 3 0.8565
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.8557
Enoyl-[acyl-carrier-protein] reductase [NADH] P9WGR1 INHA_MYCTU Mycobacterium tuberculosis 3 0.8465
Rhodopsin P02699 OPSD_BOVIN Bos taurus 3 0.8459
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.8384
Lanosterol 14-alpha-demethylase Q385E8 Q385E8_TRYB2 Trypanosoma brucei brucei 4 0.8382
Vitamin D3 receptor P13053 VDR_RAT Rattus norvegicus 3 0.8361
Corticosteroid-binding globulin P08185 CBG_HUMAN Homo sapiens 3 0.8281
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 3 0.8170
Retinol-binding protein 4 P02753 RET4_HUMAN Homo sapiens 4 0.8099
Retinol-binding protein 1 P02696 RET1_RAT Rattus norvegicus 3 0.8041
Acetylcholinesterase P21836 ACES_MOUSE Mus musculus 3 0.8032
Fatty acid-binding protein, liver P80226 FABPL_CHICK Gallus gallus 3 0.7956
Vitamin D(3) 25-hydroxylase C4B644 CPVDH_PSEAH Pseudonocardia autotrophica 3 0.7897
Integrin alpha-L P20701 ITAL_HUMAN Homo sapiens 3 0.7862
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 3 0.7853
Sex hormone-binding globulin P04278 SHBG_HUMAN Homo sapiens 3 0.7848
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7835
Trichothecene 15-O-acetyltransferase TRI3 Q9C1B7 TRI3_FUSSP Fusarium sporotrichioides 3 0.7790
Putative cytochrome P450 120 Q59990 CP120_SYNY3 Synechocystis sp 3 0.7774
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.7630
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7623
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 3 0.7608
Beta-1 adrenergic receptor P07700 ADRB1_MELGA Meleagris gallopavo 3 0.7581
Methylketone synthase I E0YCS2 E0YCS2_SOLHA Solanum habrochaites 2 0.7559
Type IV / VI secretion system DotU domain-containing protein Q9KN50 Q9KN50_VIBCH Vibrio cholerae serotype O1 3 0.7536
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 2 0.7516
Cytochrome P450 Q93H81 Q93H81_STRAX Streptomyces avermitilis 3 0.7481
Retinaldehyde-binding protein 1 P12271 RLBP1_HUMAN Homo sapiens 3 0.7476
Retinol dehydratase Q26490 Q26490_SPOFR Spodoptera frugiperda 3 0.7475
17-beta-hydroxysteroid dehydrogenase type 1 P14061 DHB1_HUMAN Homo sapiens 3 0.7462
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.7429
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.7398
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 2 0.7373
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 2 0.7360
Beta-1 adrenergic receptor P07700 ADRB1_MELGA Meleagris gallopavo 3 0.7309
Vitamin D3 receptor P13053 VDR_RAT Rattus norvegicus 3 0.7298
Retinol-binding protein 4 P18902 RET4_BOVIN Bos taurus 3 0.7264
Camphor 5-monooxygenase P00183 CPXA_PSEPU Pseudomonas putida 3 0.7241
Retinol-binding protein 2 P50120 RET2_HUMAN Homo sapiens 3 0.7175
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7172
Abscisic acid receptor PYL10 Q8H1R0 PYL10_ARATH Arabidopsis thaliana 3 0.7159
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7120
Abscisic acid receptor PYR1 O49686 PYR1_ARATH Arabidopsis thaliana 2 0.7102
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 2 0.7098
Beta-1 adrenergic receptor P07700 ADRB1_MELGA Meleagris gallopavo 3 0.7093
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7093
Retinol-binding protein 2 P50120 RET2_HUMAN Homo sapiens 3 0.7088
Gag-Pol polyprotein P03366 POL_HV1B1 Human immunodeficiency virus type 1 group M subtype B 3 0.7081
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7064
Sulfotransferase 2B1 O00204 ST2B1_HUMAN Homo sapiens 2 0.7054
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7023
Abscisic acid receptor PYL3 Q9SSM7 PYL3_ARATH Arabidopsis thaliana 2 0.7003

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