Psymberin, (+)-

Details

• Internal ID: ab1c5bb4-baed-437a-8cc5-b4a7ade21314
• Taxonomy: Benzenoids > Benzene and substituted derivatives > Benzoic acids and derivatives > Hydroxybenzoic acid derivatives
• IUPAC Name: (2S,3S)-N-[(S)-[(2S,4R,6R)-6-[(2S,3R)-3-[(3R)-6,8-dihydroxy-5-methyl-1-oxo-3,4-dihydroisochromen-3-yl]-2-hydroxybutyl]-4-hydroxy-5,5-dimethyloxan-2-yl]-methoxymethyl]-2-hydroxy-3-methoxy-5-methylhex-5-enamide
• InChI: InChI=1S/C31H47NO11/c1-14(2)9-22(40-7)27(37)28(38)32-29(41-8)23-13-24(36)31(5,6)25(42-23)12-19(34)16(4)21-10-17-15(3)18(33)11-20(35)26(17)30(39)43-21/h11,16,19,21-25,27,29,33-37H,1,9-10,12-13H2,2-8H3,(H,32,38)/t16-,19+,21-,22+,23+,24-,25-,27+,29+/m1/s1
• InChI Key: BNNIEBYABSNREN-CYRUSRGFSA-N
• Popularity: 77 references in papers

Physical and Chemical Properties

• Molecular Formula: C₃₁H₄₇NO₁₁
• Molecular Weight: 609.70 g/mol
• Exact Mass: 609.31491132 g/mol
• Topological Polar Surface Area (TPSA): 184.00 Ų
• XlogP: 3.70
• Atomic LogP (AlogP): 1.85
• H-Bond Acceptor: 11
• H-Bond Donor: 6
• Rotatable Bonds: 12

Synonyms

• IRCINIASTATIN A
• 714954-37-7
• (2S,3S)-N-[(S)-[(2S,4R,6R)-6-[(2S,3R)-3-[(3R)-6,8-dihydroxy-5-methyl-1-oxo-3,4-dihydroisochromen-3-yl]-2-hydroxybutyl]-4-hydroxy-5,5-dimethyloxan-2-yl]-methoxymethyl]-2-hydroxy-3-methoxy-5-methylhex-5-enamide
• (+)-psymberin
• (2S,3S)-N-((S)-((2S,4R,6R)-6-((2S,3R)-3-((3R)-3,4-Dihydro-6,8-dihydroxy-5-methyl-1-oxo-1H-2-benzopyran-3-yl)-2-hydroxybutyl)tetrahydro-4-hydroxy-5,5-dimethyl-2H-pyran-2-yl)methoxymethyl)-2-hydroxy-3-methoxy-5-methyl-5-hexenamide
• (2S,3S)-N-[(S)-[(2S,4R,6R)-6-[(2S,3R)-3-[(3R)-3,4-Dihydro-6,8-dihydroxy-5-methyl-1-oxo-1H-2-benzopyran-3-yl]-2-hydroxybutyl]tetrahydro-4-hydroxy-5,5-dimethyl-2H-pyran-2-yl]methoxymethyl]-2-hydroxy-3-methoxy-5-methyl-5-hexenamide
• Psymberin, (+)-
• (+)-Irciniastatin A
• (+)-Iriciniastatin A
• SAK6W44ZUP
• SCHEMBL13496618
• CHEBI:182709
• DTXSID301098104
• 5-Hexenamide, N-((S)-((2S,4R,6R)-6-((2S,3R)-3-((3R)-3,4-dihydro-6,8-dihydroxy-5-methyl-1-oxo-1H-2-benzopyran-3-yl)-2-hydroxybutyl)tetrahydro-4-hydroxy-5,5-dimethyl-2H-pyran-2-yl)methoxymethyl)-2-hydroxy-3-methoxy-5-methyl-, (2S,3S)-

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.8198	81.98%
Caco-2	-	0.8254	82.54%
Blood Brain Barrier	-	0.9000	90.00%
Human oral bioavailability	-	0.7143	71.43%
Subcellular localzation	Mitochondria	0.4391	43.91%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8009	80.09%
OATP1B3 inhibitior	+	0.9063	90.63%
MATE1 inhibitior	-	0.8446	84.46%
OCT2 inhibitior	-	0.9500	95.00%
BSEP inhibitior	-	0.5000	50.00%
P-glycoprotein inhibitior	+	0.6952	69.52%
P-glycoprotein substrate	+	0.7739	77.39%
CYP3A4 substrate	+	0.7212	72.12%
CYP2C9 substrate	-	0.5900	59.00%
CYP2D6 substrate	-	0.8600	86.00%
CYP3A4 inhibition	-	0.7771	77.71%
CYP2C9 inhibition	-	0.7839	78.39%
CYP2C19 inhibition	-	0.8141	81.41%
CYP2D6 inhibition	-	0.9108	91.08%
CYP1A2 inhibition	-	0.7104	71.04%
CYP2C8 inhibition	+	0.6312	63.12%
CYP inhibitory promiscuity	-	0.7836	78.36%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.9800	98.00%
Carcinogenicity (trinary)	Non-required	0.5623	56.23%
Eye corrosion	-	0.9878	98.78%
Eye irritation	-	0.9230	92.30%
Skin irritation	-	0.7632	76.32%
Skin corrosion	-	0.9303	93.03%
Ames mutagenesis	-	0.7100	71.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4218	42.18%
Micronuclear	+	0.7500	75.00%
Hepatotoxicity	+	0.7292	72.92%
skin sensitisation	-	0.8376	83.76%
Respiratory toxicity	+	0.7889	78.89%
Reproductive toxicity	+	0.9778	97.78%
Mitochondrial toxicity	+	0.9750	97.50%
Nephrotoxicity	+	0.6144	61.44%
Acute Oral Toxicity (c)	III	0.5345	53.45%
Estrogen receptor binding	+	0.7598	75.98%
Androgen receptor binding	+	0.6670	66.70%
Thyroid receptor binding	+	0.5309	53.09%
Glucocorticoid receptor binding	+	0.7905	79.05%
Aromatase binding	+	0.7805	78.05%
PPAR gamma	+	0.6880	68.80%
Honey bee toxicity	-	0.6126	61.26%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	-	0.6347	63.47%
Fish aquatic toxicity	+	0.9763	97.63%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	99.62%	91.11%
CHEMBL1951	P21397	Monoamine oxidase A	99.21%	91.49%
CHEMBL4040	P28482	MAP kinase ERK2	99.10%	83.82%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	98.62%	85.14%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	98.60%	94.45%
CHEMBL2581	P07339	Cathepsin D	98.56%	98.95%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	95.87%	96.09%
CHEMBL1806	P11388	DNA topoisomerase II alpha	92.47%	89.00%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	91.14%	95.89%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	90.13%	95.50%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	89.44%	91.07%
CHEMBL340	P08684	Cytochrome P450 3A4	89.41%	91.19%
CHEMBL3137262	O60341	LSD1/CoREST complex	88.81%	97.09%
CHEMBL3060	Q9Y345	Glycine transporter 2	88.39%	99.17%
CHEMBL3401	O75469	Pregnane X receptor	88.34%	94.73%
CHEMBL4657	Q6V1X1	Dipeptidyl peptidase VIII	87.82%	97.21%
CHEMBL1907602	P06493	Cyclin-dependent kinase 1/cyclin B1	86.18%	91.24%
CHEMBL5608	Q16288	NT-3 growth factor receptor	86.18%	95.89%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	85.09%	97.14%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	84.45%	99.23%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	84.42%	95.56%
CHEMBL2413	P32246	C-C chemokine receptor type 1	83.59%	89.50%
CHEMBL3880	P07900	Heat shock protein HSP 90-alpha	82.72%	96.21%
CHEMBL5028	O14672	ADAM10	82.50%	97.50%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	82.48%	96.95%
CHEMBL3130	O00329	PI3-kinase p110-delta subunit	82.11%	96.47%
CHEMBL5697	Q9GZT9	Egl nine homolog 1	81.15%	93.40%
CHEMBL3359	P21462	Formyl peptide receptor 1	81.12%	93.56%
CHEMBL4685	P14902	Indoleamine 2,3-dioxygenase	80.12%	96.38%

Plants that contains it

There are no matching plants.

Cross-Links

• PubChem: 11692946
• LOTUS: LTS0268912
• wikiData: Q104250715