hyacinthacine C2

Details

• Internal ID: cd13a55e-54c9-4aa4-b155-15706a4c56b4
• Taxonomy: Organoheterocyclic compounds > Pyrrolizidines
• IUPAC Name: (1S,2R,3R,5S,7S,8R)-3,5-bis(hydroxymethyl)-2,3,5,6,7,8-hexahydro-1H-pyrrolizine-1,2,7-triol
• SMILES (Canonical): C1C(N2C(C(C(C2C1O)O)O)CO)CO
• SMILES (Isomeric): C1[C@H](N2[C@@H]([C@H]([C@H]([C@H]2[C@H]1O)O)O)CO)CO
• InChI: InChI=1S/C9H17NO5/c11-2-4-1-6(13)7-9(15)8(14)5(3-12)10(4)7/h4-9,11-15H,1-3H2/t4-,5+,6-,7+,8+,9-/m0/s1
• InChI Key: FKQQQROPNALGDM-ARADLNFTSA-N
• Popularity: 2 references in papers

Physical and Chemical Properties

• Molecular Formula: C₉H₁₇NO₅
• Molecular Weight: 219.23 g/mol
• Exact Mass: 219.11067264 g/mol
• Topological Polar Surface Area (TPSA): 104.00 Ų
• XlogP: -2.30
• Atomic LogP (AlogP): -3.12
• H-Bond Acceptor: 6
• H-Bond Donor: 5
• Rotatable Bonds: 2

Synonyms

• RefChem:146945
• (1S,2R,3R,5S,7S,8R)-3,5-bis(hydroxymethyl)-2,3,5,6,7,8-hexahydro-1H-pyrrolizine-1,2,7-triol
• CHEMBL226576
• BDBM50214382
• [(1S*,2R*,3R*,5R*,7S*,7a*R)-3,5-dihydroxymethyl-1,2,7-trihydroxypyrrolizidine]

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.8531	85.31%
Caco-2	-	0.9109	91.09%
Blood Brain Barrier	+	0.6000	60.00%
Human oral bioavailability	+	0.7571	75.71%
Subcellular localzation	Lysosomes	0.5250	52.50%
OATP2B1 inhibitior	-	0.8551	85.51%
OATP1B1 inhibitior	+	0.9646	96.46%
OATP1B3 inhibitior	+	0.9440	94.40%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	-	0.8500	85.00%
BSEP inhibitior	-	0.9393	93.93%
P-glycoprotein inhibitior	-	0.9816	98.16%
P-glycoprotein substrate	-	0.8864	88.64%
CYP3A4 substrate	-	0.5987	59.87%
CYP2C9 substrate	-	0.5905	59.05%
CYP2D6 substrate	+	0.5956	59.56%
CYP3A4 inhibition	-	0.9798	97.98%
CYP2C9 inhibition	-	0.9129	91.29%
CYP2C19 inhibition	-	0.9353	93.53%
CYP2D6 inhibition	-	0.9366	93.66%
CYP1A2 inhibition	-	0.8511	85.11%
CYP2C8 inhibition	-	0.9376	93.76%
CYP inhibitory promiscuity	-	0.9828	98.28%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.9400	94.00%
Carcinogenicity (trinary)	Non-required	0.5994	59.94%
Eye corrosion	-	0.9799	97.99%
Eye irritation	-	0.8191	81.91%
Skin irritation	-	0.7330	73.30%
Skin corrosion	-	0.8967	89.67%
Ames mutagenesis	-	0.5300	53.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.6612	66.12%
Micronuclear	+	0.7200	72.00%
Hepatotoxicity	-	0.5500	55.00%
skin sensitisation	-	0.8895	88.95%
Respiratory toxicity	+	0.5444	54.44%
Reproductive toxicity	+	0.6556	65.56%
Mitochondrial toxicity	+	0.8125	81.25%
Nephrotoxicity	-	0.5817	58.17%
Acute Oral Toxicity (c)	III	0.4689	46.89%
Estrogen receptor binding	-	0.8663	86.63%
Androgen receptor binding	-	0.6467	64.67%
Thyroid receptor binding	-	0.7310	73.10%
Glucocorticoid receptor binding	-	0.7260	72.60%
Aromatase binding	-	0.8558	85.58%
PPAR gamma	-	0.8527	85.27%
Honey bee toxicity	-	0.7512	75.12%
Biodegradation	-	0.5000	50.00%
Crustacea aquatic toxicity	-	0.7800	78.00%
Fish aquatic toxicity	-	0.9794	97.94%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL4176	P04066	Alpha-L-fucosidase I	17000 nM	IC50	PMID: 25380299

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	96.66%	96.09%
CHEMBL3137262	O60341	LSD1/CoREST complex	93.00%	97.09%
CHEMBL4040	P28482	MAP kinase ERK2	91.06%	83.82%
CHEMBL226	P30542	Adenosine A1 receptor	90.74%	95.93%
CHEMBL4394	Q9NYA1	Sphingosine kinase 1	90.47%	96.03%
CHEMBL3023	Q9NRA0	Sphingosine kinase 2	85.59%	95.61%
CHEMBL230	P35354	Cyclooxygenase-2	82.35%	89.63%

Plants that contains it

• Ledebouria socialis

Cross-Links

• PubChem: 16737240
• NPASS: NPC184150
• ChEMBL: CHEMBL226576
• LOTUS: LTS0163377
• wikiData: Q104996748