Canophyllol

Details

• Internal ID: ad8f8adf-25a2-4ec1-b6af-f953617363dc
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Triterpenoids
• IUPAC Name: (4R,4aS,6aS,6aS,6bR,8aS,12aS,14aS,14bS)-8a-(hydroxymethyl)-4,4a,6a,6b,11,11,14a-heptamethyl-2,4,5,6,6a,7,8,9,10,12,12a,13,14,14b-tetradecahydro-1H-picen-3-one
• SMILES (Canonical): CC1C(=O)CCC2C1(CCC3C2(CCC4(C3(CCC5(C4CC(CC5)(C)C)CO)C)C)C)C
• SMILES (Isomeric): C[C@H]1C(=O)CC[C@@H]2[C@@]1(CC[C@H]3[C@]2(CC[C@@]4([C@@]3(CC[C@@]5([C@H]4CC(CC5)(C)C)CO)C)C)C)C
• InChI: InChI=1S/C30H50O2/c1-20-21(32)8-9-22-26(20,4)11-10-23-27(22,5)13-14-29(7)24-18-25(2,3)12-16-30(24,19-31)17-15-28(23,29)6/h20,22-24,31H,8-19H2,1-7H3/t20-,22+,23-,24-,26+,27-,28+,29-,30+/m0/s1
• InChI Key: YPWQSKQSNNTXOL-TWWFCBCGSA-N
• Popularity: 58 references in papers

Physical and Chemical Properties

• Molecular Formula: C₃₀H₅₀O₂
• Molecular Weight: 442.70 g/mol
• Exact Mass: 442.381080833 g/mol
• Topological Polar Surface Area (TPSA): 37.30 Ų
• XlogP: 8.20
• Atomic LogP (AlogP): 7.43
• H-Bond Acceptor: 2
• H-Bond Donor: 1
• Rotatable Bonds: 1

Synonyms

• 14440-41-6
• 28-Hydroxy-D:A-friedooleanan-3-one
• (4R,4aS,6aS,6aS,6bR,8aS,12aS,14aS,14bS)-8a-(hydroxymethyl)-4,4a,6a,6b,11,11,14a-heptamethyl-2,4,5,6,6a,7,8,9,10,12,12a,13,14,14b-tetradecahydro-1H-picen-3-one
• D:A-Friedooleanan-3-one, 28-hydroxy-
• 28-Hydroxyfriedelin
• CHEMBL483012
• SCHEMBL4413819
• DTXSID101035465
• AKOS040740310

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9967	99.67%
Caco-2	-	0.5153	51.53%
Blood Brain Barrier	+	0.8000	80.00%
Human oral bioavailability	-	0.5143	51.43%
Subcellular localzation	Mitochondria	0.8093	80.93%
OATP2B1 inhibitior	-	0.7187	71.87%
OATP1B1 inhibitior	+	0.9161	91.61%
OATP1B3 inhibitior	+	0.9091	90.91%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	+	0.6186	61.86%
BSEP inhibitior	+	0.8577	85.77%
P-glycoprotein inhibitior	-	0.7487	74.87%
P-glycoprotein substrate	-	0.7968	79.68%
CYP3A4 substrate	+	0.6624	66.24%
CYP2C9 substrate	-	0.8190	81.90%
CYP2D6 substrate	-	0.7841	78.41%
CYP3A4 inhibition	-	0.8125	81.25%
CYP2C9 inhibition	-	0.5753	57.53%
CYP2C19 inhibition	-	0.8255	82.55%
CYP2D6 inhibition	-	0.9574	95.74%
CYP1A2 inhibition	-	0.5837	58.37%
CYP2C8 inhibition	-	0.8125	81.25%
CYP inhibitory promiscuity	-	0.9126	91.26%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.9600	96.00%
Carcinogenicity (trinary)	Non-required	0.6882	68.82%
Eye corrosion	-	0.9759	97.59%
Eye irritation	-	0.8964	89.64%
Skin irritation	-	0.7244	72.44%
Skin corrosion	-	0.9733	97.33%
Ames mutagenesis	-	0.6870	68.70%
Human Ether-a-go-go-Related Gene inhibition	+	0.6467	64.67%
Micronuclear	-	0.9900	99.00%
Hepatotoxicity	-	0.7926	79.26%
skin sensitisation	-	0.5994	59.94%
Respiratory toxicity	+	0.6000	60.00%
Reproductive toxicity	+	0.7333	73.33%
Mitochondrial toxicity	-	0.5125	51.25%
Nephrotoxicity	-	0.6377	63.77%
Acute Oral Toxicity (c)	III	0.8265	82.65%
Estrogen receptor binding	+	0.7781	77.81%
Androgen receptor binding	+	0.6677	66.77%
Thyroid receptor binding	+	0.6264	62.64%
Glucocorticoid receptor binding	+	0.7641	76.41%
Aromatase binding	+	0.6985	69.85%
PPAR gamma	+	0.5570	55.70%
Honey bee toxicity	-	0.8539	85.39%
Biodegradation	-	0.7000	70.00%
Crustacea aquatic toxicity	-	0.5800	58.00%
Fish aquatic toxicity	+	0.9407	94.07%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL253	P34972	Cannabinoid CB2 receptor	94.25%	97.25%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	91.02%	91.11%
CHEMBL2581	P07339	Cathepsin D	90.83%	98.95%
CHEMBL3137262	O60341	LSD1/CoREST complex	90.62%	97.09%
CHEMBL1994	P08235	Mineralocorticoid receptor	90.32%	100.00%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	90.20%	96.09%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	87.62%	82.69%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	87.43%	95.56%
CHEMBL1937	Q92769	Histone deacetylase 2	84.20%	94.75%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	84.02%	94.45%
CHEMBL2664	P23526	Adenosylhomocysteinase	83.60%	86.67%
CHEMBL1871	P10275	Androgen Receptor	81.38%	96.43%

Plants that contains it

• Amanoa oblongifolia
• Balanops australiana
• Calophyllum brasiliense
• Calophyllum calaba
• Calophyllum cordato-oblongum
• Calophyllum inophyllum
• Calophyllum lankaensis
• Calophyllum pinetorum
• Calophyllum walkeri
• Crocus sieberi
• Curculigo orchioides
• Elaeodendron croceum
• Elaeodendron transvaalense
• Eugenia myrcianthes
• Euonymus revolutus
• Garcinia cymosa
• Garcinia gardneriana
• Garcinia subelliptica
• Garcinia xanthochymus
• Gymnosporia diversifolia
• Gynochthodes officinalis
• Jacobaea persoonii
• Lepidobotrys staudtii
• Lithocarpus haipinii
• Maytenus laevis
• Montanoa karwinskii
• Plenckia populnea
• Ruptiliocarpon caracolito
• Salacia petenensis
• Salix babylonica
• Semialarium mexicanum
• Strychnos decussata
• Tanaecium jaroba
• Tripterygium wilfordii
• Verbena bonariensis
• Xanthocercis zambesiaca

Cross-Links

• PubChem: 7330581
• NPASS: NPC180777
• ChEMBL: CHEMBL483012
• LOTUS: LTS0143411
• wikiData: Q103813465