Terpendole I

Details

• Internal ID: be04101e-d64d-4d17-ae99-e8c6a73bbc74
• Taxonomy: Organoheterocyclic compounds > Naphthopyrans
• IUPAC Name: (1S,2R,5S,7S,8R,9R,11S,12S,15S)-7-(2-hydroxypropan-2-yl)-1,2-dimethyl-6,10-dioxa-24-azaheptacyclo[13.10.0.02,12.05,11.09,11.017,25.018,23]pentacosa-17(25),18,20,22-tetraene-8,12-diol
• SMILES (Canonical): CC12CCC3C4(C1(CCC5C2(C6=C(C5)C7=CC=CC=C7N6)C)O)C(O4)C(C(O3)C(C)(C)O)O
• SMILES (Isomeric): C[C@]12CC[C@H]3[C@@]4([C@@]1(CC[C@@H]5[C@@]2(C6=C(C5)C7=CC=CC=C7N6)C)O)[C@H](O4)[C@@H]([C@H](O3)C(C)(C)O)O
• InChI: InChI=1S/C27H35NO5/c1-23(2,30)21-19(29)22-27(33-22)18(32-21)10-11-24(3)25(4)14(9-12-26(24,27)31)13-16-15-7-5-6-8-17(15)28-20(16)25/h5-8,14,18-19,21-22,28-31H,9-13H2,1-4H3/t14-,18-,19+,21-,22+,24+,25+,26-,27-/m0/s1
• InChI Key: AKOANWZRKXOJTC-ZWNZASDISA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₂₇H₃₅NO₅
• Molecular Weight: 453.60 g/mol
• Exact Mass: 453.25152322 g/mol
• Topological Polar Surface Area (TPSA): 98.20 Ų
• XlogP: 3.00
• Atomic LogP (AlogP): 2.96
• H-Bond Acceptor: 5
• H-Bond Donor: 4
• Rotatable Bonds: 1

Synonyms

• 167612-17-1
• (1S,2R,5S,7S,8R,9R,11S,12S,15S)-7-(2-hydroxypropan-2-yl)-1,2-dimethyl-6,10-dioxa-24-azaheptacyclo[13.10.0.02,12.05,11.09,11.017,25.018,23]pentacosa-17(25),18,20,22-tetraene-8,12-diol
• (1S,2R,5S,7S,8R,9R,11S,12S,15S)-7-(2-hydroxypropan-2-yl)-1,2-dimethyl-6,10-dioxa-24-azaheptacyclo(13.10.0.02,12.05,11.09,11.017,25.018,23)pentacosa-17(25),18,20,22-tetraene-8,12-diol
• RefChem:188031
• (2S,3R,3aR,4aS,4bS,6aS,12bS,12cR,14aS)-3,3a,5,6,6a,7,12,12b,12c,13,14,14a-dodecahydro-2-(1-hydroxy-1-methylethyl)-12b,12c-dimethyl-2H,4bH-oxireno[4',4'a]-1-benzopyrano[5',6':6,7]indeno[1,2-b]indole-3,4b-diol
• orb1693836
• SCHEMBL20869892
• CHEBI:144412
• HY-N8331
• CS-0143226
• C20543

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9587	95.87%
Caco-2	-	0.7005	70.05%
Blood Brain Barrier	+	0.5750	57.50%
Human oral bioavailability	-	0.6429	64.29%
Subcellular localzation	Lysosomes	0.3371	33.71%
OATP2B1 inhibitior	-	0.8617	86.17%
OATP1B1 inhibitior	+	0.8735	87.35%
OATP1B3 inhibitior	+	0.9314	93.14%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.7821	78.21%
BSEP inhibitior	+	0.9115	91.15%
P-glycoprotein inhibitior	-	0.6107	61.07%
P-glycoprotein substrate	+	0.6076	60.76%
CYP3A4 substrate	+	0.7117	71.17%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.7328	73.28%
CYP3A4 inhibition	-	0.8498	84.98%
CYP2C9 inhibition	-	0.8573	85.73%
CYP2C19 inhibition	-	0.8254	82.54%
CYP2D6 inhibition	-	0.9075	90.75%
CYP1A2 inhibition	-	0.5855	58.55%
CYP2C8 inhibition	+	0.6779	67.79%
CYP inhibitory promiscuity	-	0.8314	83.14%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9000	90.00%
Carcinogenicity (trinary)	Non-required	0.5873	58.73%
Eye corrosion	-	0.9881	98.81%
Eye irritation	-	0.9574	95.74%
Skin irritation	-	0.7500	75.00%
Skin corrosion	-	0.9182	91.82%
Ames mutagenesis	-	0.5370	53.70%
Human Ether-a-go-go-Related Gene inhibition	-	0.5141	51.41%
Micronuclear	-	0.5500	55.00%
Hepatotoxicity	-	0.6375	63.75%
skin sensitisation	-	0.8206	82.06%
Respiratory toxicity	+	0.7889	78.89%
Reproductive toxicity	+	0.9000	90.00%
Mitochondrial toxicity	+	0.9000	90.00%
Nephrotoxicity	+	0.5456	54.56%
Acute Oral Toxicity (c)	III	0.6214	62.14%
Estrogen receptor binding	+	0.8578	85.78%
Androgen receptor binding	+	0.7147	71.47%
Thyroid receptor binding	+	0.6393	63.93%
Glucocorticoid receptor binding	+	0.7383	73.83%
Aromatase binding	+	0.7979	79.79%
PPAR gamma	+	0.7394	73.94%
Honey bee toxicity	-	0.8445	84.45%
Biodegradation	-	0.9250	92.50%
Crustacea aquatic toxicity	+	0.6500	65.00%
Fish aquatic toxicity	+	0.8948	89.48%

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	97.02%	91.11%
CHEMBL1951	P21397	Monoamine oxidase A	95.73%	91.49%
CHEMBL1806	P11388	DNA topoisomerase II alpha	95.21%	89.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	94.79%	95.56%
CHEMBL216	P11229	Muscarinic acetylcholine receptor M1	93.81%	94.23%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	93.71%	96.09%
CHEMBL2035	P08912	Muscarinic acetylcholine receptor M5	93.46%	94.62%
CHEMBL253	P34972	Cannabinoid CB2 receptor	93.11%	97.25%
CHEMBL3310	Q96DB2	Histone deacetylase 11	88.45%	88.56%
CHEMBL2581	P07339	Cathepsin D	88.27%	98.95%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	86.69%	94.00%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	86.22%	94.45%
CHEMBL255	P29275	Adenosine A2b receptor	86.07%	98.59%
CHEMBL1821	P08173	Muscarinic acetylcholine receptor M4	85.61%	94.08%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	85.53%	99.23%
CHEMBL3192	Q9BY41	Histone deacetylase 8	85.38%	93.99%
CHEMBL3137262	O60341	LSD1/CoREST complex	85.13%	97.09%
CHEMBL5608	Q16288	NT-3 growth factor receptor	84.84%	95.89%
CHEMBL2535	P11166	Glucose transporter	84.75%	98.75%
CHEMBL3351	Q13085	Acetyl-CoA carboxylase 1	84.67%	93.04%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	83.90%	97.14%
CHEMBL2096618	P11274	Bcr/Abl fusion protein	82.73%	85.83%
CHEMBL1163125	O60885	Bromodomain-containing protein 4	82.51%	97.31%
CHEMBL3920	Q04759	Protein kinase C theta	82.38%	97.69%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	81.72%	92.62%
CHEMBL1994	P08235	Mineralocorticoid receptor	81.63%	100.00%
CHEMBL2265	P23141	Acyl coenzyme A:cholesterol acyltransferase	81.58%	85.94%
CHEMBL5028	O14672	ADAM10	81.45%	97.50%
CHEMBL2335	P42785	Lysosomal Pro-X carboxypeptidase	81.36%	100.00%
CHEMBL213	P08588	Beta-1 adrenergic receptor	81.29%	95.56%
CHEMBL2959	Q08881	Tyrosine-protein kinase ITK/TSK	80.69%	95.00%

Plants that contains it

• Cordia americana

Cross-Links

• PubChem: 10026941
• LOTUS: LTS0169127
• wikiData: Q105187780