Sapelenin D - Compound Card

Sapelenin D

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Sapelenin D

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)OC(=O)C)\C)/CC/C=C(/CCC=C(C)C)\C
InChI InChI=1S/C32H56O5/c1-24(2)14-12-17-26(4)19-13-18-25(3)15-10-11-16-27(5)20-21-30(37-28(6)33)32(9,36)23-22-29(34)31(7,8)35/h14-16,19,29-30,34-36H,10-13,17-18,20-23H2,1-9H3/b25-15+,26-19+,27-16+/t29?,30?,32-/m1/s1
InChIKey ASYOJPLQOSAOMD-HIZICJKISA-N
Formula C32H56O5
HBA 5
HBD 3
MW 520.8
Rotatable Bonds 18
TPSA 86.99
LogP 7.51
Number Rings 0
Number Aromatic Rings 0
Heavy Atom Count 37
Formal Charge 0
Fraction CSP3 0.72
Exact Mass 520.41
Number of Lipinski Rule Violations 2
# Species Family Kingdom NCBI Taxonomy ID
1 Entandrophragma cylindricum Meliaceae Plantae 179994

Showing of synonyms

  • Ngnokam D, Massiot G, et al. (1995). Sapelenin D, a New Acyclic Triterpenoid from the Stem Bark of Entandrophragma cylindricum. Natural Product Letters, 1995, 5(4), 289–293. [View]

No compound-protein relationship available.

No scaffolds available.

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.77
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.99
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Substrate
Skin Permeability
-3.05

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.9
Plasma Protein Binding
36.07
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
-0.59
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
1.16
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.56
Liver Injury II
Safe
hERG Blockers
Safe
Daphnia Maga
7.04
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
-140.07
Rat (Acute)
1.57
Rat (Chronic Oral)
2.54
Fathead Minnow
6.12
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
460.33
Hydration Free Energy
-3.11
Log(D) at pH=7.4
3.78
Log(P)
7.69
Log S
-5.34
Log(Vapor Pressure)
-7.58
Melting Point
44.28
pKa Acid
10.5
pKa Basic
6.11
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Rhodopsin P02699 OPSD_BOVIN Bos taurus 3 0.9715
Bacteriorhodopsin P02945 BACR_HALSA Halobacterium salinarum 3 0.9548
Retinol-binding protein 1 P02696 RET1_RAT Rattus norvegicus 3 0.9546
Beta-lactoglobulin P02754 LACB_BOVIN Bos taurus 3 0.9466
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.9345
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.9055
Cholesterol side-chain cleavage enzyme, mitochondrial P05108 CP11A_HUMAN Homo sapiens 3 0.8990
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.8915
Neocarzinostatin P0A3R9 NCZS_STRCZ Streptomyces carzinostaticus 3 0.8884
Retinol-binding protein 2 P50120 RET2_HUMAN Homo sapiens 3 0.8874
Prolyl tripeptidyl peptidase Q7MUW6 PTP_PORGI Porphyromonas gingivalis 3 0.8868
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 3 0.8832
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.8690
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 3 0.8604
Retinol dehydratase Q26490 Q26490_SPOFR Spodoptera frugiperda 3 0.8561
Beta-lactoglobulin P02754 LACB_BOVIN Bos taurus 3 0.8505
Vitamin D(3) 25-hydroxylase C4B644 CPVDH_PSEAH Pseudonocardia autotrophica 3 0.8502
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8497
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.8449
Cartilage oligomeric matrix protein P35444 COMP_RAT Rattus norvegicus 3 0.8346
Sulfotransferase 2B1 O00204 ST2B1_HUMAN Homo sapiens 2 0.8345
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.8339
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8293
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.8293
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 3 0.8228
Retinol-binding protein 1 P09455 RET1_HUMAN Homo sapiens 3 0.8219
Corticosteroid-binding globulin P31211 CBG_RAT Rattus norvegicus 4 0.8186
Putative cytochrome P450 120 Q59990 CP120_SYNY3 Synechocystis sp 3 0.8141
Retinol-binding protein 4 P18902 RET4_BOVIN Bos taurus 3 0.8131
Nuclear receptor ROR-gamma P51449 RORG_HUMAN Homo sapiens 3 0.8108
Retinol-binding protein 4 P18902 RET4_BOVIN Bos taurus 3 0.8099
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 3 0.8098
Probable NDP-rhamnosyltransferase Q9ALM8 Q9ALM8_SACSN Saccharopolyspora spinosa 3 0.8087
Retinoic acid receptor gamma P13631 RARG_HUMAN Homo sapiens 3 0.8070
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.8069
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.8017
Retinol-binding protein 4 P18902 RET4_BOVIN Bos taurus 3 0.8003
3-ketosteroid dehydrogenase Q9RA02 Q9RA02_RHOER Rhodococcus erythropolis 2 0.7998
Phospholipase A2, major isoenzyme P00592 PA21B_PIG Sus scrofa 4 0.7974
Retinoic acid receptor RXR-alpha P28700 RXRA_MOUSE Mus musculus 3 0.7973
Retinaldehyde-binding protein 1 P12271 RLBP1_HUMAN Homo sapiens 3 0.7967
17-beta-hydroxysteroid dehydrogenase type 1 P14061 DHB1_HUMAN Homo sapiens 2 0.7901
Aldo-keto reductase family 1 member C1 Q04828 AK1C1_HUMAN Homo sapiens 2 0.7898
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.7898
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 2 0.7896
Retinol-binding protein 2 P50120 RET2_HUMAN Homo sapiens 3 0.7890
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 3 0.7890
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 2 0.7877
11-beta-hydroxysteroid dehydrogenase 1 P50172 DHI1_MOUSE Mus musculus 3 0.7877
Hemolymph juvenile hormone binding protein Q9U556 Q9U556_BOMMO Bombyx mori 3 0.7863
Peptidyl-prolyl cis-trans isomerase FKBP1A P62942 FKB1A_HUMAN Homo sapiens 3 0.7862
Protein BRASSINOSTEROID INSENSITIVE 1 O22476 BRI1_ARATH Arabidopsis thaliana 3 0.7857
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 3 0.7857
3-alpha-hydroxysteroid dehydrogenase P23457 DIDH_RAT Rattus norvegicus 2 0.7834
Cellular retinol-binding protein type II Q8UVG6 Q8UVG6_DANRE Danio rerio 3 0.7814
Retinaldehyde-binding protein 1 P12271 RLBP1_HUMAN Homo sapiens 3 0.7812
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7811
Mineralocorticoid receptor P08235 MCR_HUMAN Homo sapiens 4 0.7787
Retinol-binding protein 2 P50120 RET2_HUMAN Homo sapiens 3 0.7778
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7769
Protein BRASSINOSTEROID INSENSITIVE 1 O22476 BRI1_ARATH Arabidopsis thaliana 3 0.7759
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 3 0.7755
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7738
Lanosterol synthase P48449 ERG7_HUMAN Homo sapiens 3 0.7735
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7725
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 2 0.7715
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 2 0.7707
Prostaglandin reductase 2 Q8N8N7 PTGR2_HUMAN Homo sapiens 2 0.7701
17-beta-hydroxysteroid dehydrogenase type 1 P14061 DHB1_HUMAN Homo sapiens 2 0.7700
Beta-1 adrenergic receptor P07700 ADRB1_MELGA Meleagris gallopavo 2 0.7695
Cytochrome P450 monooxygenase Q5YNS8 Q5YNS8_NOCFA Nocardia farcinica 2 0.7694
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7680
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7675
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 2 0.7665
Corticosteroid-binding globulin P08185 CBG_HUMAN Homo sapiens 2 0.7664
Vitamin D3 receptor P13053 VDR_RAT Rattus norvegicus 3 0.7662
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7643
Fatty acid-binding protein, liver P80226 FABPL_CHICK Gallus gallus 2 0.7643
Acetylcholinesterase P21836 ACES_MOUSE Mus musculus 3 0.7641
Retinoic acid receptor beta P10826 RARB_HUMAN Homo sapiens 3 0.7633
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7632
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7630
11-beta-hydroxysteroid dehydrogenase 1 P28845 DHI1_HUMAN Homo sapiens 3 0.7619
Retinol-binding protein 1 P02696 RET1_RAT Rattus norvegicus 3 0.7615
4,4'-diapophytoene synthase A9JQL9 CRTM_STAAU Staphylococcus aureus 2 0.7613
Aldo-keto reductase family 1 member C3 P42330 AK1C3_HUMAN Homo sapiens 3 0.7613
Methylketone synthase I E0YCS2 E0YCS2_SOLHA Solanum habrochaites 2 0.7612
Adenylate cyclase type 5 P30803 ADCY5_CANLF Canis lupus familiaris 4 0.7595
Cholesterol side-chain cleavage enzyme, mitochondrial P00189 CP11A_BOVIN Bos taurus 3 0.7595
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 3 0.7581
Lanosterol 14-alpha-demethylase Q385E8 Q385E8_TRYB2 Trypanosoma brucei brucei 3 0.7567
Beta-elicitin cryptogein P15570 ELIB_PHYCR Phytophthora cryptogea 3 0.7560
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7557
Fatty acid-binding protein 10-A, liver basic Q9I8L5 FA10A_DANRE Danio rerio 2 0.7555
Gastrotropin Q6IMW5 Q6IMW5_DANRE Danio rerio 2 0.7548
Enoyl-[acyl-carrier-protein] reductase [NADH] P9WGR1 INHA_MYCTU Mycobacterium tuberculosis 2 0.7531
Cytochrome P450 monooxygenase Q5YNS8 Q5YNS8_NOCFA Nocardia farcinica 2 0.7519
Beta-1 adrenergic receptor P07700 ADRB1_MELGA Meleagris gallopavo 3 0.7509
Integrin alpha-L P20701 ITAL_HUMAN Homo sapiens 3 0.7498
Mineralocorticoid receptor P08235 MCR_HUMAN Homo sapiens 4 0.7493
17-beta-hydroxysteroid dehydrogenase type 1 P14061 DHB1_HUMAN Homo sapiens 2 0.7479
Acetylcholinesterase P04058 ACES_TETCF Tetronarce californica 3 0.7468
Abscisic acid receptor PYL3 Q9SSM7 PYL3_ARATH Arabidopsis thaliana 2 0.7468
Aromatase P11511 CP19A_HUMAN Homo sapiens 3 0.7464
Abscisic acid receptor PYR1 O49686 PYR1_ARATH Arabidopsis thaliana 2 0.7459
Soluble cytochrome b562 P0ABE7 C562_ECOLX Escherichia coli 2 0.7453
Beta-lactoglobulin P02754 LACB_BOVIN Bos taurus 2 0.7453
Steroid C26-monooxygenase P9WPP1 CP125_MYCTU Mycobacterium tuberculosis 2 0.7441
NPC intracellular cholesterol transporter 1 O15118 NPC1_HUMAN Homo sapiens 3 0.7436
Beta-1 adrenergic receptor P07700 ADRB1_MELGA Meleagris gallopavo 3 0.7434
Vitamin D3 receptor P13053 VDR_RAT Rattus norvegicus 3 0.7430
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 3 0.7424
Progesterone receptor P06401 PRGR_HUMAN Homo sapiens 2 0.7424
Epoxide hydrolase Q41415 Q41415_SOLTU Solanum tuberosum 2 0.7418
Rhodopsin P02699 OPSD_BOVIN Bos taurus 2 0.7410
Steroid 17-alpha-hydroxylase/17,20 lyase P05093 CP17A_HUMAN Homo sapiens 2 0.7409
Retinol-binding protein 2 P06768 RET2_RAT Rattus norvegicus 3 0.7407
Alcohol dehydrogenase 1C P00326 ADH1G_HUMAN Homo sapiens 2 0.7406
Protein BRASSINOSTEROID INSENSITIVE 1 O22476 BRI1_ARATH Arabidopsis thaliana 3 0.7400
Methylketone synthase I E0YCS2 E0YCS2_SOLHA Solanum habrochaites 2 0.7397
Sulfotransferase 2B1 O00204 ST2B1_HUMAN Homo sapiens 2 0.7391
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 2 0.7384
Beta-1 adrenergic receptor P07700 ADRB1_MELGA Meleagris gallopavo 2 0.7373
Nuclear receptor coactivator 2 Q15596 NCOA2_HUMAN Homo sapiens 3 0.7371
Serpin domain-containing protein H0ZQY2 H0ZQY2_TAEGU Taeniopygia guttata 3 0.7369
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7366
Peroxisome proliferator-activated receptor gamma P37231 PPARG_HUMAN Homo sapiens 2 0.7341
Nuclear receptor subfamily 1 group I member 3 O35627 NR1I3_MOUSE Mus musculus 2 0.7336
Acetylcholinesterase P21836 ACES_MOUSE Mus musculus 2 0.7331
Retinol-binding protein 4 P18902 RET4_BOVIN Bos taurus 3 0.7330
Vitamin D-binding protein P02774 VTDB_HUMAN Homo sapiens 2 0.7327
Mineralocorticoid receptor P08235 MCR_HUMAN Homo sapiens 2 0.7322
Chloramphenicol acetyltransferase P62577 CAT_ECOLX Escherichia coli 3 0.7276
Beta-1 adrenergic receptor P07700 ADRB1_MELGA Meleagris gallopavo 2 0.7273
Abscisic acid receptor PYL10 Q8H1R0 PYL10_ARATH Arabidopsis thaliana 3 0.7261
Thyroid hormone receptor alpha P04625 THA_CHICK Gallus gallus 3 0.7251
Cellular retinoic acid-binding protein 2 P29373 RABP2_HUMAN Homo sapiens 2 0.7237
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7234
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7225
Sulfotransferase 2A1 Q06520 ST2A1_HUMAN Homo sapiens 2 0.7224
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 2 0.7214
Glucocorticoid receptor P04150 GCR_HUMAN Homo sapiens 4 0.7210
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 3 0.7203
Aromatase P11511 CP19A_HUMAN Homo sapiens 2 0.7203
Nuclear receptor subfamily 1 group I member 2 O75469 NR1I2_HUMAN Homo sapiens 4 0.7194
Gag-Pol polyprotein P03366 POL_HV1B1 Human immunodeficiency virus type 1 group M subtype B 3 0.7193
Vitamin D3 receptor P13053 VDR_RAT Rattus norvegicus 3 0.7188
Steroid 21-hydroxylase P08686 CP21A_HUMAN Homo sapiens 2 0.7185
Adenylate cyclase type 5 P30803 ADCY5_CANLF Canis lupus familiaris 4 0.7182
Sex hormone-binding globulin P04278 SHBG_HUMAN Homo sapiens 3 0.7167
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 2 0.7162
Trichodiene synthase P13513 TRI5_FUSSP Fusarium sporotrichioides 2 0.7157
Abscisic acid receptor PYL2 O80992 PYL2_ARATH Arabidopsis thaliana 2 0.7154
Oxysterols receptor LXR-beta P55055 NR1H2_HUMAN Homo sapiens 3 0.7145
Protein farnesyltransferase/geranylgeranyltransferase type-1 subunit alpha Q04631 FNTA_RAT Rattus norvegicus 3 0.7138
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 3 0.7117
Retinoic acid receptor RXR Q8T5C6 RXR_BIOGL Biomphalaria glabrata 3 0.7106
Retinol-binding protein 4 P02753 RET4_HUMAN Homo sapiens 3 0.7100
Adenylate cyclase type 5 P30803 ADCY5_CANLF Canis lupus familiaris 4 0.7077
Beta-1 adrenergic receptor P07700 ADRB1_MELGA Meleagris gallopavo 3 0.7071
Vitamin D3 receptor P13053 VDR_RAT Rattus norvegicus 3 0.7046
Abscisic acid receptor PYR1 O49686 PYR1_ARATH Arabidopsis thaliana 3 0.7018
Cytochrome P450 monooxygenase Q5YNS8 Q5YNS8_NOCFA Nocardia farcinica 2 0.7016
17-beta-hydroxysteroid dehydrogenase type 1 P14061 DHB1_HUMAN Homo sapiens 2 0.7003
Nuclear receptor ROR-beta P45446 RORB_RAT Rattus norvegicus 2 0.7003

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