Cytochalasin B

Details

• Internal ID: 8a5b423a-8154-453d-aec9-f590e45e239f
• Taxonomy: Alkaloids and derivatives > Cytochalasans > Cytochalasins
• IUPAC Name: (1S,4E,6R,10R,12E,14S,15S,17S,18S,19S)-19-benzyl-6,15-dihydroxy-10,17-dimethyl-16-methylidene-2-oxa-20-azatricyclo[12.7.0.01,18]henicosa-4,12-diene-3,21-dione
• SMILES (Canonical): CC1CCCC(C=CC(=O)OC23C(C=CC1)C(C(=C)C(C2C(NC3=O)CC4=CC=CC=C4)C)O)O
• SMILES (Isomeric): C[C@@H]1CCC[C@H](/C=C/C(=O)O[C@]23[C@@H](/C=C/C1)[C@@H](C(=C)[C@H]([C@H]2[C@@H](NC3=O)CC4=CC=CC=C4)C)O)O
• InChI: InChI=1S/C29H37NO5/c1-18-9-7-13-22(31)15-16-25(32)35-29-23(14-8-10-18)27(33)20(3)19(2)26(29)24(30-28(29)34)17-21-11-5-4-6-12-21/h4-6,8,11-12,14-16,18-19,22-24,26-27,31,33H,3,7,9-10,13,17H2,1-2H3,(H,30,34)/b14-8+,16-15+/t18-,19-,22-,23+,24+,26+,27-,29-/m1/s1
• InChI Key: GBOGMAARMMDZGR-TYHYBEHESA-N
• Popularity: 5,123 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₉H₃₇NO₅
• Molecular Weight: 479.60 g/mol
• Exact Mass: 479.26717328 g/mol
• Topological Polar Surface Area (TPSA): 95.90 Ų
• XlogP: 3.40
• Atomic LogP (AlogP): 3.49
• H-Bond Acceptor: 5
• H-Bond Donor: 3
• Rotatable Bonds: 2

Synonyms

• Phomin
• 14930-96-2
• CHEBI:23527
• TAMM
• 3CHI920QS7
• DTXSID30893482
• NSC-107658
• (1S,4E,6R,10R,12E,14S,15S,17S,18S,19S)-19-benzyl-6,15-dihydroxy-10,17-dimethyl-16-methylidene-2-oxa-20-azatricyclo[12.7.0.01,18]henicosa-4,12-diene-3,21-dione
• 24-Oxa(14)cytochalasa-6(12),13,21-triene-1,23-dione, 7,20-dihydroxy-16-methyl-10-phenyl-, (7S,13E,16R,20R,21E)-
• 2H-Oxacyclotetradecino(2,3-d)isoindole-2,18(5H)-dione, 6,7,8,9,10,12a,13,14,15,15a,16,17-dodecahydro-5,13-dihydroxy-9,15-dimethyl-14-methylene-16-(phenylmethyl)-, (3E,5R,9R,11E,12aS,13S,15S,15aS,16S,18aS)-
• (1S,4E,6R,10R,12E,14S,15S,17S,18S,19S)-19-benzyl-6,15-dihydroxy-10,17-dimethyl-16-methylidene-2-oxa-20-azatricyclo(12.7.0.01,18)henicosa-4,12-diene-3,21-dione
• RefChem:130322
• DTXCID201323499
• 16-benzyl-5,13-dihydroxy-9,15-dimethyl-14-methylidene-2H,5H,6H,7H,8H,9H,10H,13H,14H,15H,15aH,16H,17H,18H,18bH-oxacyclotetradeca(3,2-e)isoindole-2,18-dione
• 239-000-2
• cytochalasin-B
• C29H37NO5
• MFCD00077704
• Cytochalasin B (Phomin)
• MLS000028816
• SMR000058787
• (4Z,12Z)-19-Benzyl-6,15-dihydroxy-10,17-dimethyl-16-methylidene-2-oxa-20-azatricyclo[12.7.0.01,18]henicosa-4,12-diene-3,21-dione
• MLS002703001
• UNII-3CHI920QS7
• CCRIS 9284
• NSC107658
• HSDB 3479
• 2H-Oxacyclotetradec(2,3-d)isoindole-2,18(5H)-dione, 16-benzyl-6,7,8,9,10,12a,13,14,15,15a,16,17-dodecahydro-5,13-dihydroxy-9,15-dimethyl-14-methylene-, (E,E)-(5S,9R,12aS,13S,15S,15aS,16S,18aS)-
• EINECS 239-000-2
• ROTHWEILER
• BRN 1096207
• Cytochalasin B from Drechslera dematioidea
• Opera_ID_1877
• Spectrum5_001780
• CYTOCHALASIN B [MI]
• BSPBio_001600
• MLS001148651
• CYTOCHALASIN B [HSDB]
• CHEMBL411729
• GTPL5334
• SCHEMBL20063279
• BCBcMAP01_000011
• REGID_for_CID_5311281
• GLXC-23589
• HMS1361P22
• HMS1791P22
• HMS1989P22
• HMS3402P22
• BDBM50478403
• CCG-39777
• LMPK11000002
• AKOS025311470
• FC11288
• 7,20-Dihydroxy-10-phenyl-5,16-dimethyl-24-oxa-(14)cytochalas-6(12),13,21-trien-23-one
• IDI1_034070
• NCGC00163439-01
• NCGC00163439-02
• NCGC00163439-04
• (E,E)-(5S,9R,12aS,13S,15S,15aS,16S,18aS)-16-Benzyl-6,7,8,9,10,12a,13,14,15,15a,16,17-dodecahydro-5,13-dihydroxy-9,15-dimethyl-14-methylene-2H-oxacyclotetradec(2,3-d)isoindole-2,18(5H)-dione
• HY-16928
• CS-0012975
• NS00011654
• C19954
• Cytochalasin B from Helminthosporium dematioideum
• Q26998028
• Cytochalasin B from Drechslera dematioidea, >=98% (HPLC), powder
• (3E,5R,9R,11E,12aS,13S,15S,15aS,16S,18aS)-16-Benzyl-5,13-dihydroxy-9,15-dimethyl-14-methylene-6,7,8,9,10,12a,13,14,15,15a,16,17-dodecahydro-2H-oxacyclotetradecino[2,3-d]isoindole-2,18(5H)-dione
• (3E,5R,9R,11E,12aS,13S,15S,15aS,16S,18aS)-16-benzyl-5,13-dihydroxy-9,15-dimethyl-14-methylidene-6,7,8,9,10,12a,13,14,15,15a,16,17-dodecahydro-2H-oxacyclotetradecino[2,3-d]isoindole-2,18(5H)-dione
• 11032-95-4
• 2H-Oxacyclotetradec(2,3-d)isoindole-2,18(5H)-dione, 16-benzyl-6,7,8,9,10,12a,13,14,15,15a,16,17-dodecahydro-5,13-dihydroxy-9,15-dimethyl-14-methylene-, (E)-(5S,9R,12aS,13S,15S,15aS,16aS,18aS)-
• 2H-OXACYCLOTETRADECINO(2,3-D)ISOINDOLE-2,18(5H)-DIONE, 16-BENZYL-6,7,8,9,10,12A,13,14,15,15A,16,17-DODECAHYDRO-5,13-DIHYDROXY-9,15-DIMETHYL-14-METHYLENE-, (E,E)-(5R,9R,12AS,13S,15S,15AS,16S,18AS)-
• 2H-Oxacyclotetradecino(2,3-d)isoindole-2,18(5H)-dione, 16-benzyl-6,7,8,9,10,12a,13,14,15,15a,16,17-dodecahydro-5,13-dihydroxy-9,15-dimethyl-14-methylene-, (E,E)-(5S,9R,12aS,13S,15S,15aS,16S,18aS)-
• 2H-OXACYCLOTETRADECINO(2,3-D)ISOINDOLE-2,18(5H)-DIONE, 6,7,8,9,10,12A,13,14,15,15A,16,17-DODECAHYDRO-5,13-DIHYDROXY-9,15-DIMETHYL-14-METHYLENE-16-(PHENYLMETHYL)-, (5R-(3E,5R*,9R*,11E,12AS*,13S*,15S*,15AS*,16S*,18AS*))-

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9762	97.62%
Caco-2	-	0.8162	81.62%
Blood Brain Barrier	+	0.5500	55.00%
Human oral bioavailability	-	0.5143	51.43%
Subcellular localzation	Mitochondria	0.5128	51.28%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8120	81.20%
OATP1B3 inhibitior	+	0.9100	91.00%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	-	0.7322	73.22%
BSEP inhibitior	+	0.7708	77.08%
P-glycoprotein inhibitior	-	0.7683	76.83%
P-glycoprotein substrate	+	0.6212	62.12%
CYP3A4 substrate	+	0.6822	68.22%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8750	87.50%
CYP3A4 inhibition	-	0.7240	72.40%
CYP2C9 inhibition	-	0.8573	85.73%
CYP2C19 inhibition	-	0.8075	80.75%
CYP2D6 inhibition	-	0.9326	93.26%
CYP1A2 inhibition	-	0.8518	85.18%
CYP2C8 inhibition	+	0.6459	64.59%
CYP inhibitory promiscuity	-	0.6783	67.83%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9500	95.00%
Carcinogenicity (trinary)	Danger	0.4648	46.48%
Eye corrosion	-	0.9914	99.14%
Eye irritation	-	0.9690	96.90%
Skin irritation	-	0.6958	69.58%
Skin corrosion	-	0.9233	92.33%
Ames mutagenesis	-	0.6700	67.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.6446	64.46%
Micronuclear	+	0.7300	73.00%
Hepatotoxicity	+	0.5960	59.60%
skin sensitisation	-	0.8270	82.70%
Respiratory toxicity	+	0.7889	78.89%
Reproductive toxicity	+	0.9556	95.56%
Mitochondrial toxicity	+	0.9375	93.75%
Nephrotoxicity	+	0.4567	45.67%
Acute Oral Toxicity (c)	III	0.4483	44.83%
Estrogen receptor binding	+	0.6967	69.67%
Androgen receptor binding	+	0.6474	64.74%
Thyroid receptor binding	-	0.5348	53.48%
Glucocorticoid receptor binding	+	0.7916	79.16%
Aromatase binding	+	0.6217	62.17%
PPAR gamma	+	0.7130	71.30%
Honey bee toxicity	-	0.7902	79.02%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	+	0.6300	63.00%
Fish aquatic toxicity	+	0.9851	98.51%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL4040	P28482	MAP kinase ERK2	8912.5 nM	Potency	via CMAUP
CHEMBL1293277	O15118	Niemann-Pick C1 protein	1122 nM	Potency	via CMAUP
CHEMBL1293235	P02545	Prelamin-A/C	631 nM; 631 nM	Potency; Potency	via CMAUP; via Super-PRED
CHEMBL1293294	P51151	Ras-related protein Rab-9A	6309.6 nM	Potency	via CMAUP

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL2581	P07339	Cathepsin D	99.16%	98.95%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	97.34%	91.11%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	96.31%	95.56%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	95.86%	96.09%
CHEMBL3137262	O60341	LSD1/CoREST complex	94.03%	97.09%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	88.70%	90.71%
CHEMBL5608	Q16288	NT-3 growth factor receptor	88.70%	95.89%
CHEMBL1293249	Q13887	Kruppel-like factor 5	88.33%	86.33%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	88.29%	95.50%
CHEMBL2693	Q9UIQ6	Cystinyl aminopeptidase	87.66%	97.64%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	87.09%	94.45%
CHEMBL221	P23219	Cyclooxygenase-1	83.01%	90.17%
CHEMBL4523377	Q86WV6	Stimulator of interferon genes protein	82.13%	95.48%

Plants that contains it

• Aconitum brevicalcaratum
• Cirsium arvense
• Cirsium dipsacolepis
• Crinum kirkii
• Cytisus scoparius
• Dalea elegans
• Heliomeris longifolia var. annua
• Hypericum triquetrifolium
• Isodon japonicus
• Knightia deplanchei
• Mallotus rhamnifolius
• Malva sylvestris
• Mesembryanthemum emarcidum
• Nephroia diversifolia
• Nerium oleander
• Plantago lanceolata
• Ptilidium ciliare
• Scutellaria seleriana
• Solanum pimpinellifolium
• Sonchus arvensis
• Sophora conollyi
• Teucrium pestalozzae
• Trichotosia subsessilis
• Trifolium apertum
• Tripodanthus acutifolius
• Veronica pectinata

Cross-Links

• PubChem: 5311281
• NPASS: NPC31171
• ChEMBL: CHEMBL411729
• LOTUS: LTS0242278
• wikiData: Q26998028