Sapelenin B - Compound Card

Sapelenin B

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Sapelenin B

Structure
Zoomed Structure
  • Family: Plantae - Meliaceae
  • Kingdom: Plantae
  • Class: Terpenoid
    • Subclass: Acyclic Triterpenoid
Canonical Smiles C/C(=C\CC/C=C(/CCC(C(CCC(C(O)(C)C)O)(O)C)O)\C)/CC/C=C(/CCC=C(C)C)\C
InChI InChI=1S/C30H54O4/c1-23(2)13-11-16-25(4)18-12-17-24(3)14-9-10-15-26(5)19-20-28(32)30(8,34)22-21-27(31)29(6,7)33/h13-15,18,27-28,31-34H,9-12,16-17,19-22H2,1-8H3/b24-14+,25-18+,26-15+
InChIKey ILPRRIDIERTIPO-IEYWHCGYSA-N
Formula C30H54O4
HBA 4
HBD 4
MW 478.76
Rotatable Bonds 17
TPSA 80.92
LogP 6.94
Number Rings 0
Number Aromatic Rings 0
Heavy Atom Count 34
Formal Charge 0
Fraction CSP3 0.73
Exact Mass 478.4
Number of Lipinski Rule Violations 1
# Species Family Kingdom NCBI Taxonomy ID
1 Entandrophragma cylindricum Meliaceae Plantae 179994

Showing of synonyms

  • Ngnokam D, Massiot G, et al. (1993). Sapelenins A, B and C, acyclic triterpenoids from the stem bark of Entandrophragma cylindricum. Phytochemistry, 1993, 34(6), 1603-1607. [View]

No compound-protein relationship available.

No scaffolds available.

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.95
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.95
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Substrate
Skin Permeability
-3.0

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
1.08
Plasma Protein Binding
26.12
Steady State Volume of Distribution
-

Metabolism

Breast Cancer Resistance Protein
Non-Inhibitor
CYP 1A2 Inhibitor
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
-1.1
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
1.21
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.06
Liver Injury II
Safe
hERG Blockers
Safe
Daphnia Maga
5.94
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
-34.28
Rat (Acute)
1.54
Rat (Chronic Oral)
2.8
Fathead Minnow
5.79
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
447.81
Hydration Free Energy
-4.29
Log(D) at pH=7.4
3.79
Log(P)
7.06
Log S
-4.92
Log(Vapor Pressure)
-7.53
Melting Point
52.16
pKa Acid
9.84
pKa Basic
6.81
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 0.9624
Rhodopsin P02699 OPSD_BOVIN Bos taurus 3 0.9371
Beta-lactoglobulin P02754 LACB_BOVIN Bos taurus 3 0.9301
17-beta-hydroxysteroid dehydrogenase type 1 P14061 DHB1_HUMAN Homo sapiens 3 0.9183
Vitamin D3 receptor P13053 VDR_RAT Rattus norvegicus 3 0.9137
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 3 0.9117
Beta-lactoglobulin P02754 LACB_BOVIN Bos taurus 3 0.9082
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.9061
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.9041
Bacteriorhodopsin P02945 BACR_HALSA Halobacterium salinarum 3 0.8981
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 3 0.8923
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.8888
Retinol dehydratase Q26490 Q26490_SPOFR Spodoptera frugiperda 3 0.8789
Probable NDP-rhamnosyltransferase Q9ALM8 Q9ALM8_SACSN Saccharopolyspora spinosa 3 0.8765
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.8751
Sex hormone-binding globulin P04278 SHBG_HUMAN Homo sapiens 3 0.8467
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8465
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.8413
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 3 0.8382
Peptidyl-prolyl cis-trans isomerase FKBP1A P62942 FKB1A_HUMAN Homo sapiens 4 0.8378
Cholesterol side-chain cleavage enzyme, mitochondrial P05108 CP11A_HUMAN Homo sapiens 3 0.8374
Vitamin D(3) 25-hydroxylase C4B644 CPVDH_PSEAH Pseudonocardia autotrophica 3 0.8321
Prolyl tripeptidyl peptidase Q7MUW6 PTP_PORGI Porphyromonas gingivalis 3 0.8287
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.8190
Retinol-binding protein 2 P50120 RET2_HUMAN Homo sapiens 3 0.8134
Vitamin D3 receptor P13053 VDR_RAT Rattus norvegicus 3 0.8120
Phospholipase A2, major isoenzyme P00592 PA21B_PIG Sus scrofa 4 0.8112
Retinol-binding protein 2 P50120 RET2_HUMAN Homo sapiens 3 0.8108
Cellular retinol-binding protein type II Q8UVG6 Q8UVG6_DANRE Danio rerio 3 0.8077
Sulfotransferase 2B1 O00204 ST2B1_HUMAN Homo sapiens 2 0.8025
3-alpha-hydroxysteroid dehydrogenase P23457 DIDH_RAT Rattus norvegicus 3 0.8002
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 3 0.7994
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 3 0.7967
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7959
17-beta-hydroxysteroid dehydrogenase type 1 P14061 DHB1_HUMAN Homo sapiens 3 0.7958
Lanosterol 14-alpha-demethylase Q385E8 Q385E8_TRYB2 Trypanosoma brucei brucei 3 0.7955
Cartilage oligomeric matrix protein P35444 COMP_RAT Rattus norvegicus 3 0.7952
Retinaldehyde-binding protein 1 P12271 RLBP1_HUMAN Homo sapiens 3 0.7931
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 3 0.7917
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7907
Soluble cytochrome b562 P0ABE7 C562_ECOLX Escherichia coli 2 0.7903
Gastrotropin P51161 FABP6_HUMAN Homo sapiens 3 0.7890
Methylketone synthase I E0YCS2 E0YCS2_SOLHA Solanum habrochaites 2 0.7876
Beta-elicitin cryptogein P15570 ELIB_PHYCR Phytophthora cryptogea 3 0.7875
Sulfotransferase 2A1 Q06520 ST2A1_HUMAN Homo sapiens 3 0.7874
Integrin alpha-L P20701 ITAL_HUMAN Homo sapiens 3 0.7874
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7859
Aldo-keto reductase family 1 member C1 Q04828 AK1C1_HUMAN Homo sapiens 2 0.7855
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 2 0.7848
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7838
Neocarzinostatin P0A3R9 NCZS_STRCZ Streptomyces carzinostaticus 3 0.7834
NPC intracellular cholesterol transporter 1 O15118 NPC1_HUMAN Homo sapiens 3 0.7825
Putative cytochrome P450 120 Q59990 CP120_SYNY3 Synechocystis sp 3 0.7822
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7816
Beta-1 adrenergic receptor P07700 ADRB1_MELGA Meleagris gallopavo 3 0.7815
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7802
Retinol-binding protein 1 P09455 RET1_HUMAN Homo sapiens 3 0.7799
Retinoic acid receptor RXR Q8T5C6 RXR_BIOGL Biomphalaria glabrata 3 0.7799
Methylketone synthase I E0YCS2 E0YCS2_SOLHA Solanum habrochaites 2 0.7794
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 2 0.7790
Acetylcholinesterase P21836 ACES_MOUSE Mus musculus 3 0.7786
Retinol-binding protein 1 P09455 RET1_HUMAN Homo sapiens 3 0.7775
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7774
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7765
Vitamin D3 receptor P13053 VDR_RAT Rattus norvegicus 3 0.7746
Retinol-binding protein 4 P18902 RET4_BOVIN Bos taurus 3 0.7743
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 2 0.7738
Lysozyme C II P11941 LYSC2_ONCMY Oncorhynchus mykiss 3 0.7736
Retinol-binding protein 4 P18902 RET4_BOVIN Bos taurus 3 0.7731
Prostaglandin reductase 2 Q8N8N7 PTGR2_HUMAN Homo sapiens 2 0.7723
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7707
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.7691
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7679
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7672
Hemolymph juvenile hormone binding protein Q9U556 Q9U556_BOMMO Bombyx mori 3 0.7666
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7656
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7645
Lanosterol synthase P48449 ERG7_HUMAN Homo sapiens 4 0.7644
Beta-1 adrenergic receptor P07700 ADRB1_MELGA Meleagris gallopavo 3 0.7627
Abscisic acid receptor PYL3 Q9SSM7 PYL3_ARATH Arabidopsis thaliana 2 0.7627
Sulfotransferase 2A1 Q06520 ST2A1_HUMAN Homo sapiens 2 0.7612
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 2 0.7604
Beta-lactoglobulin P02754 LACB_BOVIN Bos taurus 2 0.7588
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 2 0.7581
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 2 0.7580
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 3 0.7579
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7578
Cellular retinoic acid-binding protein 2 P29373 RABP2_HUMAN Homo sapiens 2 0.7572
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7563
Retinoic acid receptor beta P10826 RARB_HUMAN Homo sapiens 3 0.7560
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 3 0.7540
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 2 0.7530
Progesterone receptor P06401 PRGR_HUMAN Homo sapiens 2 0.7528
11-beta-hydroxysteroid dehydrogenase 1 P50172 DHI1_MOUSE Mus musculus 3 0.7526
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 3 0.7512
17-beta-hydroxysteroid dehydrogenase type 1 P14061 DHB1_HUMAN Homo sapiens 2 0.7490
Nuclear receptor ROR-alpha P35398 RORA_HUMAN Homo sapiens 3 0.7488
Corticosteroid-binding globulin P08185 CBG_HUMAN Homo sapiens 3 0.7483
Progesterone receptor P06401 PRGR_HUMAN Homo sapiens 3 0.7482
Abscisic acid receptor PYL10 Q8H1R0 PYL10_ARATH Arabidopsis thaliana 3 0.7481
Cartilage oligomeric matrix protein Q9R0G6 COMP_MOUSE Mus musculus 3 0.7451
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7450
Retinol-binding protein 2 P06768 RET2_RAT Rattus norvegicus 3 0.7434
Cytochrome P450 monooxygenase Q5YNS8 Q5YNS8_NOCFA Nocardia farcinica 2 0.7434
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 3 0.7433
Retinol-binding protein 2 P50120 RET2_HUMAN Homo sapiens 3 0.7433
Protein BRASSINOSTEROID INSENSITIVE 1 O22476 BRI1_ARATH Arabidopsis thaliana 3 0.7432
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7414
Aromatase P11511 CP19A_HUMAN Homo sapiens 2 0.7398
Serpin domain-containing protein H0ZQY2 H0ZQY2_TAEGU Taeniopygia guttata 3 0.7396
Cytochrome P450 monooxygenase Q5YNS8 Q5YNS8_NOCFA Nocardia farcinica 2 0.7392
Sulfotransferase 2B1 O00204 ST2B1_HUMAN Homo sapiens 2 0.7390
Protein farnesyltransferase/geranylgeranyltransferase type-1 subunit alpha Q04631 FNTA_RAT Rattus norvegicus 3 0.7384
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 4 0.7382
Acetylcholinesterase P21836 ACES_MOUSE Mus musculus 2 0.7363
Protein BRASSINOSTEROID INSENSITIVE 1 O22476 BRI1_ARATH Arabidopsis thaliana 3 0.7352
Abscisic acid receptor PYL2 O80992 PYL2_ARATH Arabidopsis thaliana 2 0.7342
Retinaldehyde-binding protein 1 P12271 RLBP1_HUMAN Homo sapiens 3 0.7331
Fatty acid-binding protein, liver P80226 FABPL_CHICK Gallus gallus 2 0.7326
Alcohol dehydrogenase 1C P00326 ADH1G_HUMAN Homo sapiens 2 0.7315
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 2 0.7278
Fatty acid-binding protein 10-A, liver basic Q9I8L5 FA10A_DANRE Danio rerio 2 0.7273
Peroxisome proliferator-activated receptor gamma P37231 PPARG_HUMAN Homo sapiens 2 0.7271
17-beta-hydroxysteroid dehydrogenase type 1 P14061 DHB1_HUMAN Homo sapiens 2 0.7265
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7262
Beta-1 adrenergic receptor P07700 ADRB1_MELGA Meleagris gallopavo 2 0.7262
Steroid 17-alpha-hydroxylase/17,20 lyase P05093 CP17A_HUMAN Homo sapiens 2 0.7201
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 3 0.7170
Vitamin D-binding protein P02774 VTDB_HUMAN Homo sapiens 2 0.7166
Cytochrome P450 monooxygenase Q5YNS8 Q5YNS8_NOCFA Nocardia farcinica 2 0.7159
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 2 0.7143
Epoxide hydrolase Q41415 Q41415_SOLTU Solanum tuberosum 2 0.7141
Steroid C26-monooxygenase P9WPP1 CP125_MYCTU Mycobacterium tuberculosis 3 0.7140
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7133
Nuclear receptor subfamily 1 group I member 2 O75469 NR1I2_HUMAN Homo sapiens 3 0.7130
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 2 0.7127
Abscisic acid receptor PYR1 O49686 PYR1_ARATH Arabidopsis thaliana 3 0.7122
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7084
Beta-1 adrenergic receptor P07700 ADRB1_MELGA Meleagris gallopavo 3 0.7076
3-ketosteroid dehydrogenase Q9RA02 Q9RA02_RHOER Rhodococcus erythropolis 2 0.7066
Vitamin D3 dihydroxylase P18326 CPXE_STRGO Streptomyces griseolus 3 0.7062
Albumin P02768 ALBU_HUMAN Homo sapiens 2 0.7058
Cytochrome P450 monooxygenase Q5YNS8 Q5YNS8_NOCFA Nocardia farcinica 2 0.7049
Aromatase P11511 CP19A_HUMAN Homo sapiens 2 0.7048
Camphor 5-monooxygenase P00183 CPXA_PSEPU Pseudomonas putida 3 0.7044
Retinol-binding protein 4 P02753 RET4_HUMAN Homo sapiens 3 0.7043
4,4'-diapophytoene synthase A9JQL9 CRTM_STAAU Staphylococcus aureus 2 0.7031
Phospholipase A2, major isoenzyme P00592 PA21B_PIG Sus scrofa 4 0.7014
Sulfotransferase 2A1 Q06520 ST2A1_HUMAN Homo sapiens 2 0.7004
Protein farnesyltransferase/geranylgeranyltransferase type-1 subunit alpha Q04631 FNTA_RAT Rattus norvegicus 3 0.7002

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