NPASS Compound

Natural Product: NPC162569

Natural Product ID	NPC162569
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	Casearborin E
IUPAC Name	[(1S,3R,5R,6aS,7R,8R,10S,10aS)-1,3,5-triacetyloxy-7,8-dimethyl-7-[(2E)-3-methylpenta-2,4-dienyl]-1,3,5,6,6a,8,9,10-octahydrobenzo[d][2]benzofuran-10-yl] 4-hydroxybenzoate
Synonyms	Casearborin E
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL509263
PubChem CID	10371296
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001551] Diterpenoids [CHEMONTID:0001757] Colensane and clerodane diterpenoids

The Chemical Classification was calculated by Classyfire, a software for chemical taxonomy calculation. Reference: DOI:10.1186/s13321-016-0174-y.

Chemical Representations

RDKit 3D 83 86 0 0 0 0 0 0 0 0999 V2000 -6.6883 1.4600 -2.9203 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.5617 0.9798 -2.4657 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3100 1.6862 -2.5913 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2147 1.1020 -2.0876 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8617 1.7004 -2.1365 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2168 1.8662 -0.7668 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.2607 2.7896 -0.0837 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0638 2.6335 -0.7675 C 0 0 2 0 0 0 0 0 0 0 0 0 0.4043 3.1386 -2.1565 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2756 2.0079 -0.1851 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1642 0.7613 0.5894 C 0 0 1 0 0 0 0 0 0 0 0 0 0.1414 -0.1502 -0.0300 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.1428 0.5799 0.0043 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.3573 1.0534 1.4612 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1997 0.0499 2.5205 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.4435 -0.1820 3.2081 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5436 -0.0998 4.5683 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5180 0.1857 5.2249 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.8763 -0.3573 5.1792 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7133 -1.2740 1.9648 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1185 -1.3689 0.8314 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4081 -2.4787 0.0058 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0631 -2.0272 -1.3167 O 0 0 0 0 0 0 0 0 0 0 0 0 0.7162 -0.7755 -1.1902 C 0 0 1 0 0 0 0 0 0 0 0 0 0.9554 -0.1722 -2.3825 O 0 0 0 0 0 0 0 0 0 0 0 0 2.1695 -0.1138 -3.0057 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1947 -0.6296 -2.5044 O 0 0 0 0 0 0 0 0 0 0 0 0 2.2834 0.5783 -4.3149 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2538 -3.6892 0.1817 O 0 0 0 0 0 0 0 0 0 0 0 0 0.3492 -4.9102 0.3398 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6056 -4.9844 0.3317 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.5031 -6.1130 0.5171 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4151 0.0635 0.5514 O 0 0 0 0 0 0 0 0 0 0 0 0 3.1452 -0.2063 1.7100 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6038 0.2209 2.7865 O 0 0 0 0 0 0 0 0 0 0 0 0 4.4137 -0.9075 1.7442 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0081 -1.0962 2.9833 C 0 0 0 0 0 0 0 0 0 0 0 0 6.2056 -1.7478 3.1363 C 0 0 0 0 0 0 0 0 0 0 0 0 6.8665 -2.2444 2.0346 C 0 0 0 0 0 0 0 0 0 0 0 0 6.3075 -2.0749 0.7963 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0852 -1.4066 0.6699 C 0 0 0 0 0 0 0 0 0 0 0 0 8.0835 -2.9124 2.1441 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.1631 3.0028 -3.2542 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.6422 0.9146 -2.8213 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.7688 2.4088 -3.4159 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.6011 0.0150 -1.9823 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.3509 0.1412 -1.6347 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.3146 1.0205 -2.8143 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.0088 2.7070 -2.6075 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.8947 3.2535 0.8232 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.2569 2.3573 -0.0814 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.3247 3.6535 -0.8222 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.0838 3.6021 -0.1906 H 0 0 0 0 0 0 0 0 0 0 0 0 0.1739 2.3980 -2.9369 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.0410 4.1329 -2.3666 H 0 0 0 0 0 0 0 0 0 0 0 0 1.5021 3.2973 -2.1766 H 0 0 0 0 0 0 0 0 0 0 0 0 1.8168 2.7352 0.5110 H 0 0 0 0 0 0 0 0 0 0 0 0 2.0808 1.8737 -0.9680 H 0 0 0 0 0 0 0 0 0 0 0 0 0.9976 0.9808 1.6392 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.9990 -0.0525 -0.2401 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.7324 1.9242 1.7067 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.4180 1.4252 1.5028 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.4809 0.2824 3.3335 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.8465 -0.2156 6.2802 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.6214 0.3629 4.7872 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.2698 -1.3601 4.9768 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.8983 -2.1325 2.5844 H 0 0 0 0 0 0 0 0 0 0 0 0 1.5058 -2.5605 -0.0012 H 0 0 0 0 0 0 0 0 0 0 0 0 1.7573 -1.1433 -0.8518 H 0 0 0 0 0 0 0 0 0 0 0 0 1.3735 1.1582 -4.5530 H 0 0 0 0 0 0 0 0 0 0 0 0 2.4955 -0.1519 -5.1256 H 0 0 0 0 0 0 0 0 0 0 0 0 3.1244 1.3300 -4.2695 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.4744 -5.8577 1.0147 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.0258 -6.8651 1.2059 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.7642 -6.6014 -0.4409 H 0 0 0 0 0 0 0 0 0 0 0 0 4.5292 -0.7262 3.8671 H 0 0 0 0 0 0 0 0 0 0 0 0 6.6860 -1.9048 4.1006 H 0 0 0 0 0 0 0 0 0 0 0 0 6.7642 -2.4362 -0.1233 H 0 0 0 0 0 0 0 0 0 0 0 0 4.6505 -1.2772 -0.3043 H 0 0 0 0 0 0 0 0 0 0 0 0 8.7889 -2.6924 1.4282 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.9658 3.8090 -2.5259 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.0764 3.2867 -3.7905 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.3677 2.9697 -4.0424 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 2 0 2 3 1 0 3 4 2 0 4 5 1 0 6 5 1 6 6 7 1 0 6 8 1 0 8 9 1 0 8 10 1 0 10 11 1 0 11 12 1 0 12 13 1 0 13 14 1 0 14 15 1 0 15 16 1 0 16 17 1 0 17 18 2 0 17 19 1 0 15 20 1 0 20 21 2 0 21 22 1 0 22 23 1 0 23 24 1 0 24 25 1 0 25 26 1 0 26 27 2 0 26 28 1 0 22 29 1 0 29 30 1 0 30 31 2 0 30 32 1 0 11 33 1 0 33 34 1 0 34 35 2 0 34 36 1 0 36 37 2 0 37 38 1 0 38 39 2 0 39 40 1 0 40 41 2 0 39 42 1 0 3 43 1 0 13 6 1 0 41 36 1 0 24 12 1 0 12 21 1 1 1 44 1 0 1 45 1 0 2 46 1 0 4 47 1 0 5 48 1 0 5 49 1 0 7 50 1 0 7 51 1 0 7 52 1 0 8 53 1 1 9 54 1 0 9 55 1 0 9 56 1 0 10 57 1 0 10 58 1 0 11 59 1 1 13 60 1 6 14 61 1 0 14 62 1 0 15 63 1 1 19 64 1 0 19 65 1 0 19 66 1 0 20 67 1 0 22 68 1 6 24 69 1 1 28 70 1 0 28 71 1 0 28 72 1 0 32 73 1 0 32 74 1 0 32 75 1 0 37 76 1 0 38 77 1 0 40 78 1 0 41 79 1 0 42 80 1 0 43 81 1 0 43 82 1 0 43 83 1 0 M END

Standard InCHIKey	NVVFTAMNEDAOEH-MYSRHRGASA-N
Standard InCHI	InChI=1S/C33H40O10/c1-8-18(2)13-14-32(7)19(3)15-28(42-29(38)23-9-11-24(37)12-10-23)33-26(16-25(17-27(32)33)39-20(4)34)30(40-21(5)35)43-31(33)41-22(6)36/h8-13,16,19,25,27-28,30-31,37H,1,14-15,17H2,2-7H3/b18-13+/t19-,25+,27+,28+,30+,31-,32-,33-/m1/s1
SMILES	C=C/C(=C/C[C@]1(C)[C@H](C)C[C@@H]([C@@]23[C@H]1C[C@@H](OC(=O)C)C=C3[C@H](O[C@H]2OC(=O)C)OC(=O)C)OC(=O)c1ccc(cc1)O)/C

Calculated Properties

Physi-Chem Properties

Molecular Weight:	596.26	Volume:	606.636 ? Van der Waals volume.
Dense:	0.983	LogP:	3.557 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	3.244 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.85 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	12.0	Rigid Bonds:	27.0
TPSA:	134.66 ? Topological Polar Surface Area.	H-Bond Acceptor:	10.0
H-Bond Donor:	1.0	Rings:	4.0
Heavy Atoms:	10.0

MedChem Properties

QED Drug-Likeness Score:	0.186	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.609	Fsp³:	0.515
MCE-18:	140.8 ? MCE-18 stands for medicinal chemistry evolution.MCE-18≥45 is considered a suitable value.	Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Rejected	GSK Rule:	Accepted
Golden Triangle Rule:	Accepted	BMS Rule:	0
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.889	Fluc inhibitor:	0.024 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.007 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.11 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.292	Promiscuous compounds:	0.339

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.02	MDCK Permeability:	-4.741
Pgp-inhibitor:	0.968	Pgp-substrate:	0.371
PAMPA:	0.455 ? The experimental data for Peff was logarithmically transformed (logPeff). Molecules with log Peff values below 2.0 were classified as low-permeability (Category 0), while those with log Peff values exceeding 2.5 were classified as high-permeability (Category 1).	Human Intestinal Absorption (HIA):	0.0
20% Bioavailability (F20%):	0.995	30% Bioavailability (F30%):	0.999
50% Bioavailability (F50%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.998
Plasma Protein Binding (PPB):	95.623%	Volume Distribution (VD):	-0.04
Fu:	4.256% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	0.878	BCRP inhibitor:	0.363
BSEP inhibitor:	0.979

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.016
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.043
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.054
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.002
CYP3A4-inhibitor:	0.002	CYP3A4-substrate:	0.977
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.999
HLM stability:	0.988 ? Human liver microsomal (HLM) stability. Category 0: stable+ (HLM > 30 min); Category 1: unstable- (HLM ≤ 30 min). The output value is the probability of human liver microsomal instability, where a value closer to 1 indicates a higher likelihood of instability.

ADMET: Excretion

Clearance (CL):

6.645

Half-life (T1/2):

0.862

ADMET: Toxicity

hERG Blockers:	0.072	hERG Blockers (10um):	0.427
Human Hepatotoxicity (H-HT):	0.239	Drug-induced Liver Injury (DILI):	0.905
AMES Toxicity:	0.919	Rat Oral Acute Toxicity:	0.858
Maximum Recommended Daily Dose:	0.989	Skin Sensitization:	0.989
Carcinogencity:	0.724	Eye Corrosion:	0.0
Eye Irritation:	0.034	Respiratory Toxicity:	0.783
Drug-induced Neurotoxicity:	0.843	Ototoxicity:	0.335
Hematotoxicity:	0.257	Drug-induced Nephrotoxicity:	0.804
Genotoxicity:	0.997	RPMI-8226 Immunitoxicity:	0.236
A549 Cytotoxicity:	0.789	Hek293 Cytotoxicity:	0.691
BCF:	0.9 ? Bioconcentration factors are used for considering secondary poisoning potential and assessing risks to human health via the food chain. The unit is -log10[(mg/L)/(1000*MW)].	IGC50:	4.089 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.583 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	5.288 ? 96 hour fathead minnow LC50. The unit of LC50FM is -log10[(mg/L)/(1000*MW)].

Species Source

Organism ID	Organism Name	Taxonomy Level	Family	SuperKingdom	Isolation Part	Collection Location	Collection Time	Reference
NPO28776	Casearia arborea	Species	Salicaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10843580]
NPO28776	Casearia arborea	Species	Salicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO28776	Casearia arborea	Species	Salicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	Organism Name	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
IC50	2

Activity Type	# Activity
Cell line	2

Molecular-level activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference

In vitro activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT390	Cell line	LOX IMVI	Homo sapiens	IC50	=	290.0	nM	PMID[15026054]
NPT374	Cell line	SF-539	Homo sapiens	IC50	=	290.0	nM	PMID[18955526]

In vivo activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference

Experimental ADME

Experiment Model	Experiment Tissue	ADME Type	ADME Relation	ADME Value	ADME Unit	Reference

Experimental Toxicity

Quantitative toxicity

Experiment Model	Experiment Organism	Toxicity Type	Toxicity Relation	Toxicity Value	Toxicity Unit	Reference

Common Abbreviations:
LC: Lethal Concentration; LD: Lethal Dose; LT:Lethal Time; NOAEL: No-observed-adverse-effect Level; BMDL: Benchmark Dose Lower Confidence Limit; BMD: Benchmark Dose; BMC:Benchmark Concentration; LOAEL: Lowest Observed Adverse Effect Level; RfD:Reference Dose; RfC:Reference Concentration; MRL: Minimal Risk Level; MEG: Maximum Exposure Guideline; PAC: Protective Action Criteria

Categorical toxicity labels

Hepatotoxicity	Carcinogenicity	Mutagenicity	Cardiotoxicity	Respiratory Toxicity	Eye Irritation	Endocrine Disruption

Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP toxicity records from domain-specific databases. These databases include:
☉ ToxValDB: a curated database that compiles quantitative toxicity values for chemicals from diverse public sources to support toxicological research and risk assessment.
☉ TOXRIC: a comprehensive, free-to-access, online database providing toxicological/feature data. The toxicity labels are retrieved from this database. [PMID: 36400569]

Chemically structural similarity

Similar Active Natural Products in NPASS

Top-200 similar NPs were calculated against the active-NP-set (includes approximately 50,000 NPs with experimentally-derived bioactivity available in NPASS)

Similarity is measured using the Tanimoto coefficient (Tc) , which compares the binary fingerprints of two molecules. Tc is calculated as the intersection divided by the union of '1' bits in the fingerprints, ranging from 0 to 1, with 1 indicating highest similarity.

● The left chart: Distribution of similarity level between NPC162569 and all remaining natural products in the NPASS database.
● The right table: Most similar natural products (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	9299
0.1-0.2	37922
0.2-0.3	2491
0.3-0.4	46
0.4-0.5	58
0.5-0.6	30
0.6-0.7	6
0.7-0.8	0
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC35160
0.7895	Intermediate Similarity	NPC267469
0.7763	Intermediate Similarity	NPC473399
0.7763	Intermediate Similarity	NPC473216
0.7101	Intermediate Similarity	NPC603601
0.6962	Remote Similarity	NPC208293
0.6901	Remote Similarity	NPC606965
0.6875	Remote Similarity	NPC116292
0.6712	Remote Similarity	NPC488235
0.6575	Remote Similarity	NPC600724
0.6533	Remote Similarity	NPC473204
0.5761	Remote Similarity	NPC320734
0.5604	Remote Similarity	NPC100420
0.5517	Remote Similarity	NPC87630
0.5455	Remote Similarity	NPC230331
0.5443	Remote Similarity	NPC602188
0.5435	Remote Similarity	NPC488962
0.5385	Remote Similarity	NPC171598
0.5375	Remote Similarity	NPC488236
0.5244	Remote Similarity	NPC201880
0.5244	Remote Similarity	NPC81567
0.5244	Remote Similarity	NPC488652
0.5181	Remote Similarity	NPC330003
0.5181	Remote Similarity	NPC473545
0.5181	Remote Similarity	NPC470321
0.5181	Remote Similarity	NPC264867
0.5181	Remote Similarity	NPC473207
0.5169	Remote Similarity	NPC179128
0.5122	Remote Similarity	NPC471366
0.5122	Remote Similarity	NPC476800
0.5122	Remote Similarity	NPC488237
0.5063	Remote Similarity	NPC472189
0.5062	Remote Similarity	NPC88507
0.5062	Remote Similarity	NPC318917
0.5062	Remote Similarity	NPC488659
0.5062	Remote Similarity	NPC481019
0.5062	Remote Similarity	NPC604149
0.506	Remote Similarity	NPC329623
0.506	Remote Similarity	NPC609711
0.5059	Remote Similarity	NPC488964
0.5059	Remote Similarity	NPC184512

Similar Clinical/Approved Drugs

Similarity level is defined by Tanimoto coefficient (Tc) between two molecules.

● The left chart: Distribution of similarity level between NPC162569 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	4635
0.1-0.2	4479
0.2-0.3	36
0.3-0.4	0
0.4-0.5	0
0.5-0.6	0
0.6-0.7	0
0.7-0.8	0
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
		NPD

Bioactivity similarity

Similar Natural Products in NPASS

Similarity level is defined by Bioactivity similarity was calculated based on bioactivity descriptors of compounds. The bioactivity descriptors were calculated by a recently developed AI algorithm Chemical Checker (CC) [Nature Biotechnology, 38:1087–1096, 2020; Nature Communications, 12:3932, 2021], which evaluated bioactivity similarities at five levels:
☉ A: chemistry similarity;
☉ B: biological targets similarity;
☉ C: networks similarity;
☉ D: cell-based bioactivity similarity;
☉ E: similarity based on clinical data.
Those 5 categories of CC bioactivity descriptors were calculated and then subjected to manifold projection using UMAP algorithm, to project all NPs on a 2-Dimensional space. The current NP was highlighted with a small circle in the 2-D map. Below figures: left-to-right, A-to-E.

A: chemistry similarity

B: biological targets similarity

C: networks similarity

D: cell-based bioactivity similarity

E: similarity based on clinical data