Dolicholide

Details

Physical and Chemical Properties

Synonyms

2D Structure

3D Structure

ADMET Properties

Targets (proven and/or predicted)

Plants that contains it

Cross-Links

Details

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Internal ID	00bb2c55-b3be-4583-a3db-d427b8e787e5
Taxonomy	Lipids and lipid-like molecules > Steroids and steroid derivatives > Steroid lactones > Brassinolides and derivatives
IUPAC Name	(1S,2R,4R,5S,7S,11S,12S,15R,16S)-15-[(2S,3R,4R)-3,4-dihydroxy-6-methyl-5-methylideneheptan-2-yl]-4,5-dihydroxy-2,16-dimethyl-9-oxatetracyclo[9.7.0.02,7.012,16]octadecan-8-one
SMILES (Canonical)	CC(C)C(=C)C(C(C(C)C1CCC2C1(CCC3C2COC(=O)C4C3(CC(C(C4)O)O)C)C)O)O
SMILES (Isomeric)	C[C@@H]([C@H]1CC[C@@H]2[C@@]1(CC[C@H]3[C@H]2COC(=O)[C@@H]4[C@@]3(C[C@H]([C@H](C4)O)O)C)C)[C@H]([C@@H](C(=C)C(C)C)O)O
InChI	InChI=1S/C28H46O6/c1-14(2)15(3)24(31)25(32)16(4)18-7-8-19-17-13-34-26(33)21-11-22(29)23(30)12-28(21,6)20(17)9-10-27(18,19)5/h14,16-25,29-32H,3,7-13H2,1-2,4-6H3/t16-,17-,18+,19-,20-,21+,22-,23+,24+,25+,27+,28+/m0/s1
InChI Key	PPFRJNLKWADOTL-WOGJWQOOSA-N
Popularity	0 references in papers

Physical and Chemical Properties

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Molecular Formula	C₂₈H₄₆O₆
Molecular Weight	478.70 g/mol
Exact Mass	478.32943918 g/mol
Topological Polar Surface Area (TPSA)	107.00 Å²
XlogP	4.70
Atomic LogP (AlogP)	3.31
H-Bond Acceptor	6
H-Bond Donor	4
Rotatable Bonds	5

Synonyms

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CHEBI:166786

DTXSID601318264

85228-11-1

(22R,23R)-2alpha,3alpha,22,23-tetrahydroxy-homo-7-oxa-5alpha-ergost-24(28)-en-6-one

(1S,2R,4R,5S,7S,11S,12S,15R,16S)-15-[(2S,3R,4R)-3,4-dihydroxy-6-methyl-5-methylideneheptan-2-yl]-4,5-dihydroxy-2,16-dimethyl-9-oxatetracyclo[9.7.0.02,7.012,16]octadecan-8-one

15-(2,3-dihydroxy-1,5-dimethyl-4-methylene-hexyl)-4,5-dihydroxy-2,16-dimethyl-9-oxatetracyclo[9.7.0.02,7.012,16]octadecan-8-one

2D Structure

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3D Structure

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ADMET Properties (via admetSAR 2)

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Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9737	97.37%
Caco-2	-	0.7164	71.64%
Blood Brain Barrier	-	0.6500	65.00%
Human oral bioavailability	-	0.5000	50.00%
Subcellular localzation	Mitochondria	0.7969	79.69%
OATP2B1 inhibitior	-	0.5733	57.33%
OATP1B1 inhibitior	+	0.8177	81.77%
OATP1B3 inhibitior	+	0.8921	89.21%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.5818	58.18%
BSEP inhibitior	-	0.4697	46.97%
P-glycoprotein inhibitior	-	0.6084	60.84%
P-glycoprotein substrate	-	0.5301	53.01%
CYP3A4 substrate	+	0.7172	71.72%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8461	84.61%
CYP3A4 inhibition	-	0.7821	78.21%
CYP2C9 inhibition	-	0.7449	74.49%
CYP2C19 inhibition	-	0.8073	80.73%
CYP2D6 inhibition	-	0.9345	93.45%
CYP1A2 inhibition	-	0.7856	78.56%
CYP2C8 inhibition	-	0.7993	79.93%
CYP inhibitory promiscuity	-	0.9537	95.37%
UGT catelyzed	+	0.9000	90.00%
Carcinogenicity (binary)	-	0.9800	98.00%
Carcinogenicity (trinary)	Non-required	0.6562	65.62%
Eye corrosion	-	0.9910	99.10%
Eye irritation	-	0.9403	94.03%
Skin irritation	+	0.5434	54.34%
Skin corrosion	-	0.9395	93.95%
Ames mutagenesis	-	0.7100	71.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4130	41.30%
Micronuclear	-	0.8600	86.00%
Hepatotoxicity	+	0.5314	53.14%
skin sensitisation	-	0.7981	79.81%
Respiratory toxicity	+	0.8222	82.22%
Reproductive toxicity	+	0.8778	87.78%
Mitochondrial toxicity	+	0.7875	78.75%
Nephrotoxicity	-	0.6616	66.16%
Acute Oral Toxicity (c)	III	0.5612	56.12%
Estrogen receptor binding	+	0.5974	59.74%
Androgen receptor binding	+	0.7225	72.25%
Thyroid receptor binding	+	0.5711	57.11%
Glucocorticoid receptor binding	+	0.6615	66.15%
Aromatase binding	+	0.5637	56.37%
PPAR gamma	+	0.5443	54.43%
Honey bee toxicity	-	0.6149	61.49%
Biodegradation	-	0.8500	85.00%
Crustacea aquatic toxicity	-	0.5400	54.00%
Fish aquatic toxicity	+	0.9952	99.52%

Targets

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Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
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	97.12%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	95.04%	96.09%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	93.68%	85.14%
CHEMBL4685	P14902	Indoleamine 2,3-dioxygenase	93.32%	96.38%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	93.05%	94.45%
CHEMBL1994	P08235	Mineralocorticoid receptor	92.81%	100.00%
CHEMBL253	P34972	Cannabinoid CB2 receptor	91.08%	97.25%
CHEMBL2581	P07339	Cathepsin D	90.23%	98.95%
CHEMBL3137262	O60341	LSD1/CoREST complex	89.96%	97.09%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	88.95%	96.77%
CHEMBL204	P00734	Thrombin	87.29%	96.01%
CHEMBL226	P30542	Adenosine A1 receptor	87.08%	95.93%
CHEMBL1806	P11388	DNA topoisomerase II alpha	85.88%	89.00%
CHEMBL1871	P10275	Androgen Receptor	83.75%	96.43%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	82.88%	99.23%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	81.49%	97.14%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	80.29%	95.89%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	80.22%	92.62%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	80.15%	90.71%

Plants that contains it

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Below are displayed all the plants proven (via scientific papers) to contain this compound!
To see more specific details click the taxa you are interested in.

Codiaeum variegatum

Croton cajucara

Digitalis isabelliana

Garcinia lancilimba

Madhuca longifolia

Pilocarpus goudotianus

Pinus elliottii

Rhizophora mucronata

Samanea saman