Cytochalasin A

Details

• Internal ID: 992f2d97-e5fb-4ab6-8c8d-dbb8c69439c1
• Taxonomy: Alkaloids and derivatives > Cytochalasans > Cytochalasins
• IUPAC Name: (1S,4E,10R,12E,14S,15S,17S,18S,19S)-19-benzyl-15-hydroxy-10,17-dimethyl-16-methylidene-2-oxa-20-azatricyclo[12.7.0.01,18]henicosa-4,12-diene-3,6,21-trione
• SMILES (Canonical): CC1CCCC(=O)C=CC(=O)OC23C(C=CC1)C(C(=C)C(C2C(NC3=O)CC4=CC=CC=C4)C)O
• SMILES (Isomeric): C[C@@H]1CCCC(=O)/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
• InChI: InChI=1S/C29H35NO5/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/h4-6,8,11-12,14-16,18-19,23-24,26-27,33H,3,7,9-10,13,17H2,1-2H3,(H,30,34)/b14-8+,16-15+/t18-,19-,23+,24+,26+,27-,29-/m1/s1
• InChI Key: ZMAODHOXRBLOQO-TZVKRXPSSA-N
• Popularity: 221 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₉H₃₅NO₅
• Molecular Weight: 477.60 g/mol
• Exact Mass: 477.25152322 g/mol
• Topological Polar Surface Area (TPSA): 92.70 Ų
• XlogP: 3.30
• Atomic LogP (AlogP): 3.70
• H-Bond Acceptor: 5
• H-Bond Donor: 2
• Rotatable Bonds: 2

Synonyms

• Dehydrophomin
• 5-Dehydrophomin
• 5,5-Didehydrophomin
• 14110-64-6
• Phomin, 5,5-didehydro-
• BV8WQ9500E
• EINECS 237-964-9
• NSC174119
• NSC 174119
• Cytochalasin A from Drechslera dematioidea
• 24-Oxa(14)cytochalasa-6(12),13,21-triene-1,20,23-trione, 7-hydroxy-16-methyl-10-phenyl-, (7S,13E,16R,21E)-
• 2H-Oxacyclotetradecino(2,3-d)isoindole-2,5,18-trione, 16-benzyl-6,7,8,9,10,12a,13,14,15,15a,16,17-dodecahydro-13-hydroxy-9,15-dimethyl-14-methylene-
• 2H-Oxacyclotetradecino(2,3-d)isoindole-2,5,18-trione, 6,7,8,9,10,12a,13,14,15,15a,16,17-dodecahydro-13-hydroxy-9,15-dimethyl-14-methylene-16-(phenylmethyl)-, (9R-(3E,9R*,11E,12aS*,13S*,15S*,15aS*,16S*,18aS*))-
• 2H-Oxacyclotetradecino(2,3-d)isoindole-2,5,18-trione, 6,7,8,9,10,12a,13,14,15,15a,16,17-dodecahydro-13-hydroxy-9,15-dimethyl-14-methylene-16-(phenylmethyl)-, (3E,9R,11E,12aS,13S,15S,15aS,16S,18aS)-
• 24-Oxa[14]cytochalasa-6(12),13,21-triene-1,20,23-trione, 7-hydroxy-16-methyl-10-phenyl-, (7S,13E,16R,21E)-
• 2H-Oxacyclotetradecino[2,3-d]isoindole-2,5,18-trione, 6,7,8,9,10,12a,13,14,15,15a,16,17-dodecahydro-13-hydroxy-9,15-dimethyl-14-methylene-16-(phenylmethyl)-, (3E,9R,11E,12aS,13S,15S,15aS,16S,18aS)-
• Spectrum5_001741
• UNII-BV8WQ9500E
• CHEBI:144392
• DTXSID401017587
• (1S,4E,10R,12E,14S,15S,17S,18S,19S)-19-benzyl-15-hydroxy-10,17-dimethyl-16-methylidene-2-oxa-20-azatricyclo[12.7.0.01,18]henicosa-4,12-diene-3,6,21-trione
• 2H-Oxacyclotetradec[2,3-d]isoindole-2,5,18-trione, 16-benzyl-6,7,8,9,10,12a,13,14,15,15a,16,17-dodecahydro-13-hydroxy-9,15-dimethyl-14-methylene-
• 7(S)-Hydroxy-16(R)-methyl-10-phenyl-24-oxa(14)cytochalasa-6(12),13(E),21(E)-triene-1,20,23-trione
• 7(S)-hydroxy-16(R)-methyl-10-phenyl-24-oxa[14]cytochalasa-6(12),13(E),21(E)-triene-1,20,23-trione
• HY-N6773
• CCG-39699
• LMPK11000001
• MFCD00005935
• AKOS030213126
• NCGC00388356-01
• benzyl-hydroxy-dimethyl-methylene-[?]trione
• CS-0091953
• C19953
• Cytochalasin A from Helminthosporium dematioideum
• J-007460
• (7S,13E,16R,21E)-7-Hydroxy-16-methyl-10-phenyl-24-oxa[14]cytochalasa-6(12),13,21-triene-1,20,23-trione
• 16-Benzyl-13-hydroxy-9,15-dimethyl-14-methylene-8,9,10,12a,13,14,15,15a,16,17-decahydro-2H-oxacyclotetradecino[2,3-d]isoindole-2,6,18(5H,7H)-trione
• 2H-Oxacyclotetradecino[2,3-d]isoindole-2,5,18-trione,6,7,8,9,10,12a,13,14,15,15a,16,17-dodecahydro-13-hydroxy-9,15-dimethyl-14-methylene-16-(phenylmethyl)-,(3E,9R,11E,12aS,13S,15S,15aS,16S,18aS)-

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9813	98.13%
Caco-2	-	0.8287	82.87%
Blood Brain Barrier	+	0.5750	57.50%
Human oral bioavailability	+	0.5429	54.29%
Subcellular localzation	Plasma membrane	0.5429	54.29%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8387	83.87%
OATP1B3 inhibitior	+	0.9164	91.64%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.6572	65.72%
BSEP inhibitior	+	0.7867	78.67%
P-glycoprotein inhibitior	-	0.9166	91.66%
P-glycoprotein substrate	+	0.5803	58.03%
CYP3A4 substrate	+	0.6690	66.90%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8583	85.83%
CYP3A4 inhibition	-	0.7024	70.24%
CYP2C9 inhibition	-	0.8708	87.08%
CYP2C19 inhibition	-	0.8275	82.75%
CYP2D6 inhibition	-	0.9222	92.22%
CYP1A2 inhibition	-	0.8206	82.06%
CYP2C8 inhibition	+	0.6313	63.13%
CYP inhibitory promiscuity	-	0.7611	76.11%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9100	91.00%
Carcinogenicity (trinary)	Danger	0.4426	44.26%
Eye corrosion	-	0.9906	99.06%
Eye irritation	-	0.9691	96.91%
Skin irritation	-	0.7044	70.44%
Skin corrosion	-	0.9186	91.86%
Ames mutagenesis	-	0.6900	69.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4137	41.37%
Micronuclear	+	0.7000	70.00%
Hepatotoxicity	+	0.5293	52.93%
skin sensitisation	-	0.8123	81.23%
Respiratory toxicity	+	0.8222	82.22%
Reproductive toxicity	+	0.8889	88.89%
Mitochondrial toxicity	+	0.8750	87.50%
Nephrotoxicity	-	0.6783	67.83%
Acute Oral Toxicity (c)	III	0.4941	49.41%
Estrogen receptor binding	+	0.6189	61.89%
Androgen receptor binding	+	0.6674	66.74%
Thyroid receptor binding	-	0.5499	54.99%
Glucocorticoid receptor binding	+	0.8078	80.78%
Aromatase binding	+	0.5340	53.40%
PPAR gamma	+	0.6979	69.79%
Honey bee toxicity	-	0.8087	80.87%
Biodegradation	-	0.8500	85.00%
Crustacea aquatic toxicity	-	0.5100	51.00%
Fish aquatic toxicity	+	0.9800	98.00%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL2581	P07339	Cathepsin D	99.10%	98.95%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	98.66%	91.11%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	96.60%	95.56%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	95.73%	96.09%
CHEMBL3137262	O60341	LSD1/CoREST complex	94.77%	97.09%
CHEMBL2693	Q9UIQ6	Cystinyl aminopeptidase	92.04%	97.64%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	88.36%	90.71%
CHEMBL1293249	Q13887	Kruppel-like factor 5	87.43%	86.33%
CHEMBL5608	Q16288	NT-3 growth factor receptor	86.69%	95.89%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	86.36%	95.50%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	86.12%	94.45%
CHEMBL4208	P20618	Proteasome component C5	84.35%	90.00%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	82.12%	99.23%
CHEMBL4581	P52732	Kinesin-like protein 1	80.14%	93.18%

Plants that contains it

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

Cross-Links

• PubChem: 5458383
• NPASS: NPC75011
• LOTUS: LTS0034598
• wikiData: Q76306426