Dihydrocephalomannine

Details

• Internal ID: d477421c-bdc8-4c9b-bbab-c73190fe55cc
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Diterpenoids > Taxanes and derivatives
• IUPAC Name: [(1S,2S,3R,4S,7R,9S,10S,12R,15S)-4,12-diacetyloxy-1,9-dihydroxy-15-[(2R,3S)-2-hydroxy-3-(2-methylbutanoylamino)-3-phenylpropanoyl]oxy-10,14,17,17-tetramethyl-11-oxo-6-oxatetracyclo[11.3.1.03,10.04,7]heptadec-13-en-2-yl] benzoate
• SMILES (Canonical): CCC(C)C(=O)NC(C1=CC=CC=C1)C(C(=O)OC2CC3(C(C4C(C(CC5C4(CO5)OC(=O)C)O)(C(=O)C(C(=C2C)C3(C)C)OC(=O)C)C)OC(=O)C6=CC=CC=C6)O)O
• SMILES (Isomeric): CCC(C)C(=O)N[C@@H](C1=CC=CC=C1)[C@H](C(=O)O[C@H]2C[C@]3([C@H]([C@H]4[C@@]([C@H](C[C@@H]5[C@]4(CO5)OC(=O)C)O)(C(=O)[C@@H](C(=C2C)C3(C)C)OC(=O)C)C)OC(=O)C6=CC=CC=C6)O)O
• InChI: InChI=1S/C45H55NO14/c1-9-23(2)39(52)46-33(27-16-12-10-13-17-27)34(50)41(54)58-29-21-45(55)38(59-40(53)28-18-14-11-15-19-28)36-43(8,30(49)20-31-44(36,22-56-31)60-26(5)48)37(51)35(57-25(4)47)32(24(29)3)42(45,6)7/h10-19,23,29-31,33-36,38,49-50,55H,9,20-22H2,1-8H3,(H,46,52)/t23?,29-,30-,31+,33-,34+,35+,36-,38-,43+,44-,45+/m0/s1
• InChI Key: OKEKLOJNCOIPIT-DYMXBOOHSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₄₅H₅₅NO₁₄
• Molecular Weight: 833.90 g/mol
• Exact Mass: 833.36225543 g/mol
• Topological Polar Surface Area (TPSA): 221.00 Ų
• XlogP: 2.20
• Atomic LogP (AlogP): 3.47
• H-Bond Acceptor: 14
• H-Bond Donor: 4
• Rotatable Bonds: 11

Synonyms

• OKEKLOJNCOIPIT-DYMXBOOHSA-
• 159001-25-9
• InChI=1/C45H55NO14/c1-9-23(2)39(52)46-33(27-16-12-10-13-17-27)34(50)41(54)58-29-21-45(55)38(59-40(53)28-18-14-11-15-19-28)36-43(8,30(49)20-31-44(36,22-56-31)60-26(5)48)37(51)35(57-25(4)47)32(24(29)3)42(45,6)7/h10-19,23,29-31,33-36,38,49-50,55H,9,20-22H2,1

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9770	97.70%
Caco-2	-	0.8852	88.52%
Blood Brain Barrier	-	0.9500	95.00%
Human oral bioavailability	-	0.8714	87.14%
Subcellular localzation	Mitochondria	0.5491	54.91%
OATP2B1 inhibitior	+	0.6331	63.31%
OATP1B1 inhibitior	-	0.5783	57.83%
OATP1B3 inhibitior	+	0.9368	93.68%
MATE1 inhibitior	-	0.8700	87.00%
OCT2 inhibitior	-	0.9500	95.00%
BSEP inhibitior	+	0.9689	96.89%
P-glycoprotein inhibitior	+	0.7888	78.88%
P-glycoprotein substrate	+	0.9397	93.97%
CYP3A4 substrate	+	0.7681	76.81%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8698	86.98%
CYP3A4 inhibition	-	0.5747	57.47%
CYP2C9 inhibition	-	0.8445	84.45%
CYP2C19 inhibition	-	0.8327	83.27%
CYP2D6 inhibition	-	0.9183	91.83%
CYP1A2 inhibition	-	0.8400	84.00%
CYP2C8 inhibition	+	0.9577	95.77%
CYP inhibitory promiscuity	-	0.7520	75.20%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.8600	86.00%
Carcinogenicity (trinary)	Non-required	0.5118	51.18%
Eye corrosion	-	0.9874	98.74%
Eye irritation	-	0.9119	91.19%
Skin irritation	-	0.7585	75.85%
Skin corrosion	-	0.9341	93.41%
Ames mutagenesis	-	0.8200	82.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.6521	65.21%
Micronuclear	+	0.7100	71.00%
Hepatotoxicity	+	0.6974	69.74%
skin sensitisation	-	0.8313	83.13%
Respiratory toxicity	+	0.9222	92.22%
Reproductive toxicity	+	0.9222	92.22%
Mitochondrial toxicity	+	0.8875	88.75%
Nephrotoxicity	-	0.6163	61.63%
Acute Oral Toxicity (c)	III	0.6252	62.52%
Estrogen receptor binding	+	0.8159	81.59%
Androgen receptor binding	+	0.8276	82.76%
Thyroid receptor binding	+	0.7132	71.32%
Glucocorticoid receptor binding	+	0.7860	78.60%
Aromatase binding	+	0.6106	61.06%
PPAR gamma	+	0.7992	79.92%
Honey bee toxicity	-	0.6575	65.75%
Biodegradation	-	0.7250	72.50%
Crustacea aquatic toxicity	+	0.5500	55.00%
Fish aquatic toxicity	+	0.9946	99.46%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL1293294	P51151	Ras-related protein Rab-9A	177.8 nM	Potency	via Super-PRED

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL221	P23219	Cyclooxygenase-1	99.92%	90.17%
CHEMBL2581	P07339	Cathepsin D	99.58%	98.95%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	98.89%	85.14%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	96.45%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	96.30%	91.11%
CHEMBL3130	O00329	PI3-kinase p110-delta subunit	93.85%	96.47%
CHEMBL1293249	Q13887	Kruppel-like factor 5	93.40%	86.33%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	92.29%	95.50%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	91.73%	94.45%
CHEMBL5028	O14672	ADAM10	91.65%	97.50%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	89.47%	95.56%
CHEMBL2535	P11166	Glucose transporter	89.43%	98.75%
CHEMBL2996	Q05655	Protein kinase C delta	89.04%	97.79%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	88.83%	96.00%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	87.94%	99.23%
CHEMBL3137262	O60341	LSD1/CoREST complex	87.61%	97.09%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	86.76%	97.14%
CHEMBL2716	Q8WUI4	Histone deacetylase 7	86.24%	89.44%
CHEMBL1806	P11388	DNA topoisomerase II alpha	85.48%	89.00%
CHEMBL3145	P42338	PI3-kinase p110-beta subunit	85.12%	98.75%
CHEMBL3060	Q9Y345	Glycine transporter 2	84.22%	99.17%
CHEMBL4267	P37173	TGF-beta receptor type II	83.95%	88.18%
CHEMBL1293277	O15118	Niemann-Pick C1 protein	83.59%	81.11%
CHEMBL340	P08684	Cytochrome P450 3A4	83.55%	91.19%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	82.43%	82.69%
CHEMBL1293267	Q9HC97	G-protein coupled receptor 35	81.20%	89.34%
CHEMBL4208	P20618	Proteasome component C5	80.46%	90.00%

Plants that contains it

• Taxus baccata

Cross-Links

• PubChem: 10509711
• NPASS: NPC215025