Cepharanthine

Details

• Internal ID: f4b504f5-1e3e-45d6-bcb7-5e93f88afd59
• Taxonomy: Lignans, neolignans and related compounds
• IUPAC Name: (14S,27R)-22,33-dimethoxy-13,28-dimethyl-2,5,7,20-tetraoxa-13,28-diazaoctacyclo[25.6.2.216,19.13,10.121,25.04,8.031,35.014,39]nonatriaconta-1(33),3(39),4(8),9,16(38),17,19(37),21,23,25(36),31,34-dodecaene
• SMILES (Canonical): CN1CCC2=CC3=C(C4=C2C1CC5=CC=C(C=C5)OC6=C(C=CC(=C6)CC7C8=CC(=C(C=C8CCN7C)OC)O4)OC)OCO3
• SMILES (Isomeric): CN1CCC2=CC3=C(C4=C2[C@@H]1CC5=CC=C(C=C5)OC6=C(C=CC(=C6)C[C@@H]7C8=CC(=C(C=C8CCN7C)OC)O4)OC)OCO3
• InChI: InChI=1S/C37H38N2O6/c1-38-13-11-24-18-31(41-4)33-20-27(24)28(38)16-23-7-10-30(40-3)32(17-23)44-26-8-5-22(6-9-26)15-29-35-25(12-14-39(29)2)19-34-36(37(35)45-33)43-21-42-34/h5-10,17-20,28-29H,11-16,21H2,1-4H3/t28-,29+/m1/s1
• InChI Key: YVPXVXANRNDGTA-WDYNHAJCSA-N
• Popularity: 538 references in papers

Physical and Chemical Properties

• Molecular Formula: C₃₇H₃₈N₂O₆
• Molecular Weight: 606.70 g/mol
• Exact Mass: 606.27298694 g/mol
• Topological Polar Surface Area (TPSA): 61.90 Ų
• XlogP: 6.50
• Atomic LogP (AlogP): 6.87
• H-Bond Acceptor: 8
• H-Bond Donor: 0
• Rotatable Bonds: 2

Synonyms

• 481-49-2
• Cepharanthin
• (+)-Cepharanthine
• O-Methylcepharanoline
• Cepharantin
• Cepharanthine [JAN]
• C37H38N2O6
• 6',12'-Dimethoxy-2,2'-dimethyl-6,7-(methylenebis(oxy))oxyacanthan
• NSC-623442
• CCRIS 6539
• NSC 623442
• BRN 0075231
• UNII-7592YJ0J6T
• CHEBI:3546
• DTXSID6045957
• 7592YJ0J6T
• NSC623442
• Cepharanthine (JAN)
• (14S,27R)-22,33-dimethoxy-13,28-dimethyl-2,5,7,20-tetraoxa-13,28-diazaoctacyclo[25.6.2.216,19.13,10.121,25.04,8.031,35.014,39]nonatriaconta-1(33),3(39),4(8),9,16(38),17,19(37),21,23,25(36),31,34-dodecaene
• Oxyacanthan, 6',12'-dimethoxy-2,2'-dimethyl-6,7-(methylenebis(oxy))-
• ecaene (non-preferred name)
• 22,33-Dimethoxy-13,28-dimethyl-2,5,7,20-tetraoxa-13,28-diazaoctacyclo[25.6.2.216,19.13,10.121,25.04,8.031,35.014,39]nonatriaconta-1(33),3(39),4(8),9,16(38),17,19(37),21,23,25(36),31,34-dodecaene
• 4-27-00-09061 (Beilstein Handbook Reference)
• DTXCID4025957
• CAS-481-49-2
• SR-01000779734
• Cepharanthin,(S)
• NCGC00095194-01
• (14S,27R)-22,33-dimethoxy-13,28-dimethyl-2,5,7,20-tetraoxa-13,28-diazaoctacyclo[25.6.2.2~16,19~.1~3,10~.1~21,25~.0~4,8~.0~14,39~.0~31,35~]nonatriaconta-1(33),3,8,10(39),16,18,21(36),22,24,31,34,37-dod
• Cepharanthine (TN)
• Spectrum2_000832
• Spectrum3_001963
• 12-O-Methylcepharanoline
• CEPHARANTHINE [MI]
• UPCMLD-DP054
• BSPBio_003563
• MLS000728518
• SCHEMBL154545
• SPECTRUM1505322
• SPBio_000783
• CEPHARANTHINE [WHO-DD]
• CHEMBL449782
• UPCMLD-DP054:001
• KBio3_002909
• Cepharanthine, >=95% (HPLC)
• Cepharanthine, >=98% (HPLC)
• HMS1922J12
• HMS2232F21
• Pharmakon1600-01505322
• HY-N6972
• Tox21_111483
• BBL030154
• BDBM50423643
• CCG-40294
• MFCD00210482
• NSC758965
• s4238
• STK801907
• AKOS004119865
• Tox21_111483_1
• NSC-758965
• SDCCGMLS-0066893.P001
• NCGC00161621-01
• NCGC00161621-02
• NCGC00161621-03
• NCGC00161621-05
• NCGC00161621-13
• AC-15206
• AS-17451
• LS-52756
• SMR000445632
• SBI-0207049.P001
• CS-0007138
• M2968
• C09391
• D01035
• AB00643356_08
• AB00643356_09
• A871948
• Q-100524
• SR-01000779734-3
• SR-01000779734-4
• BRD-K96194081-001-06-0
• Q15410888
• C1CN(C)C2Cc3ccc(OC)c(Oc4ccc(cc4)CC5N(C)CCc6cc7OCOc7c(Oc8cc2c1cc8OC)c56)c3
• (14S,27R)-22,33-dimethoxy-13,28-dimethyl-2,5,7,20-tetraoxa-13,28-diazaoctacyclo[25.6.2.2(16,19).1(3,10).1(21,25).0(4,8).0(14,39).0(31,35)]nonatriaconta-1(33),3,8,10(39),16,18,21(36),22,24,31,34,37-dodecaene
• (14S,27R)-22,33-dimethoxy-13,28-dimethyl-2,5,7,20-tetraoxa-13,28-diazaoctacyclo[25.6.2.2??,??.1?,??.1??,??.0?,?.0??,??.0??,??]nonatriaconta-1(33),3,8,10(39),16,18,21(36),22,24,31,34,37-dodecaene

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9342	93.42%
Caco-2	+	0.9313	93.13%
Blood Brain Barrier	+	0.9000	90.00%
Human oral bioavailability	-	0.6857	68.57%
Subcellular localzation	Lysosomes	0.4848	48.48%
OATP2B1 inhibitior	-	0.8589	85.89%
OATP1B1 inhibitior	+	0.9413	94.13%
OATP1B3 inhibitior	+	0.9480	94.80%
MATE1 inhibitior	-	0.8000	80.00%
OCT2 inhibitior	-	0.6000	60.00%
BSEP inhibitior	+	1.0000	100.00%
P-glycoprotein inhibitior	+	0.9665	96.65%
P-glycoprotein substrate	+	0.5888	58.88%
CYP3A4 substrate	+	0.6650	66.50%
CYP2C9 substrate	-	0.6090	60.90%
CYP2D6 substrate	+	0.6093	60.93%
CYP3A4 inhibition	-	0.8308	83.08%
CYP2C9 inhibition	-	0.8647	86.47%
CYP2C19 inhibition	-	0.6496	64.96%
CYP2D6 inhibition	+	0.5611	56.11%
CYP1A2 inhibition	-	0.6778	67.78%
CYP2C8 inhibition	+	0.4530	45.30%
CYP inhibitory promiscuity	-	0.6742	67.42%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.9800	98.00%
Carcinogenicity (trinary)	Non-required	0.5923	59.23%
Eye corrosion	-	0.9888	98.88%
Eye irritation	-	0.9475	94.75%
Skin irritation	-	0.8027	80.27%
Skin corrosion	-	0.9519	95.19%
Ames mutagenesis	+	0.9100	91.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.9549	95.49%
Micronuclear	+	0.5600	56.00%
Hepatotoxicity	-	0.9625	96.25%
skin sensitisation	-	0.8764	87.64%
Respiratory toxicity	+	0.8000	80.00%
Reproductive toxicity	+	0.8778	87.78%
Mitochondrial toxicity	+	0.7750	77.50%
Nephrotoxicity	-	0.7179	71.79%
Acute Oral Toxicity (c)	III	0.7902	79.02%
Estrogen receptor binding	+	0.6826	68.26%
Androgen receptor binding	+	0.7361	73.61%
Thyroid receptor binding	+	0.6450	64.50%
Glucocorticoid receptor binding	+	0.8831	88.31%
Aromatase binding	-	0.4834	48.34%
PPAR gamma	+	0.6100	61.00%
Honey bee toxicity	-	0.6990	69.90%
Biodegradation	-	0.8500	85.00%
Crustacea aquatic toxicity	+	0.6800	68.00%
Fish aquatic toxicity	+	0.8910	89.10%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL1293226	B2RXH2	Lysine-specific demethylase 4D-like	39810.7 nM	Potency	via CMAUP
CHEMBL1293224	P10636	Microtubule-associated protein tau	89.1 nM; 89.1 nM	Potency; Potency	via Super-PRED; via CMAUP
CHEMBL1293277	O15118	Niemann-Pick C1 protein	3981.1 nM	Potency	via CMAUP
CHEMBL1075138	Q9NUW8	Tyrosyl-DNA phosphodiesterase 1	15848.9 nM	Potency	via CMAUP

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	99.43%	96.09%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	96.04%	96.77%
CHEMBL225	P28335	Serotonin 2c (5-HT2c) receptor	94.38%	89.62%
CHEMBL2056	P21728	Dopamine D1 receptor	93.61%	91.00%
CHEMBL3192	Q9BY41	Histone deacetylase 8	93.16%	93.99%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	90.07%	95.56%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	89.47%	94.45%
CHEMBL5697	Q9GZT9	Egl nine homolog 1	89.40%	93.40%
CHEMBL5608	Q16288	NT-3 growth factor receptor	89.22%	95.89%
CHEMBL2581	P07339	Cathepsin D	89.14%	98.95%
CHEMBL4895	P30530	Tyrosine-protein kinase receptor UFO	88.92%	90.95%
CHEMBL5339	Q5NUL3	G-protein coupled receptor 120	87.41%	95.78%
CHEMBL217	P14416	Dopamine D2 receptor	87.25%	95.62%
CHEMBL2069156	Q14145	Kelch-like ECH-associated protein 1	86.99%	82.38%
CHEMBL5311	P37023	Serine/threonine-protein kinase receptor R3	86.34%	82.67%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	86.16%	85.14%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	85.01%	92.62%
CHEMBL4247	Q9UM73	ALK tyrosine kinase receptor	84.97%	96.86%
CHEMBL1293249	Q13887	Kruppel-like factor 5	84.44%	86.33%
CHEMBL5925	P22413	Ectonucleotide pyrophosphatase/phosphodiesterase family member 1	84.34%	92.38%
CHEMBL2335	P42785	Lysosomal Pro-X carboxypeptidase	84.34%	100.00%
CHEMBL1163125	O60885	Bromodomain-containing protein 4	83.83%	97.31%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	83.70%	95.89%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	83.64%	91.11%
CHEMBL2535	P11166	Glucose transporter	83.28%	98.75%
CHEMBL2413	P32246	C-C chemokine receptor type 1	83.07%	89.50%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	81.40%	94.00%
CHEMBL1806	P11388	DNA topoisomerase II alpha	80.45%	89.00%
CHEMBL5896	O75164	Lysine-specific demethylase 4A	80.32%	99.09%

Plants that contains it

• Ardisia crispa
• Doronicum grandiflorum
• Leibnitzia anandria
• Lithocarpus haipinii
• Oxytropis lanata
• Populus balsamifera
• Sphaerophysa salsula
• Stephania cephalantha
• Stephania delavayi
• Stephania epigaea
• Stephania pierrei
• Stephania sinica
• Stephania suberosa
• Strychnos gossweileri

Cross-Links

• PubChem: 10206
• NPASS: NPC73492
• ChEMBL: CHEMBL449782
• LOTUS: LTS0128547
• wikiData: Q15410888