NPASS Compound

Natural Product: NPC88557

Natural Product ID	NPC88557
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	Schisantherin A
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL565966
PubChem CID	45484556
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000238] Tannins [CHEMONTID:0001710] Hydrolyzable tannins

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 68 72 0 0 0 0 0 0 0 0999 V2000 0.1316 -4.5958 0.7128 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8794 -3.8246 1.3334 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.0185 -2.4979 0.9626 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1882 -1.9210 0.0005 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3353 -0.6068 -0.3632 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3582 0.1141 0.2804 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1868 -0.4034 1.2291 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0138 -1.7278 1.5695 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7994 -2.3595 2.5126 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.9998 -3.0330 2.2150 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1224 0.4253 1.7983 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.8830 1.1774 2.9794 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8471 1.4749 0.0951 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1705 2.7041 0.0389 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9304 3.8235 -0.0747 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3174 3.7283 -0.1325 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9366 2.4839 -0.0772 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2016 1.3258 0.0355 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7145 0.0496 0.0741 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.3059 2.6967 -0.1557 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.5504 4.0908 -0.1436 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2887 4.7038 -0.2431 O 0 0 0 0 0 0 0 0 0 0 0 0 0.2664 3.0755 0.0199 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1279 1.8702 -0.3270 C 0 0 1 0 0 0 0 0 0 0 0 0 0.7676 1.1763 -1.5851 C 0 0 2 0 0 0 0 0 0 0 0 0 0.7220 -0.3248 -1.3510 C 0 0 1 0 0 0 0 0 0 0 0 0 1.9927 -0.7262 -0.8800 O 0 0 0 0 0 0 0 0 0 0 0 0 2.8167 -1.6207 -1.5061 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4265 -2.1326 -2.5833 O 0 0 0 0 0 0 0 0 0 0 0 0 4.1147 -1.9567 -0.9165 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5091 -1.3818 0.2572 C 0 0 0 0 0 0 0 0 0 0 0 0 5.7287 -1.6830 0.8325 C 0 0 0 0 0 0 0 0 0 0 0 0 6.5945 -2.5835 0.2321 C 0 0 0 0 0 0 0 0 0 0 0 0 6.2073 -3.1688 -0.9509 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9783 -2.8528 -1.5122 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8636 1.3320 -2.6607 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3886 1.6482 -2.2081 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5499 2.4081 -0.4661 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1478 -4.2573 0.9759 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.0109 -5.6882 0.9313 H 0 0 0 0 0 0 0 0 0 0 0 0 0.0628 -4.5288 -0.4098 H 0 0 0 0 0 0 0 0 0 0 0 0 0.5866 -2.5438 -0.4594 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.5693 -3.1352 3.1631 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.8428 -4.0533 1.8229 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.6370 -2.4400 1.5151 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.8818 0.9824 3.3597 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.6932 0.9741 3.7405 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0257 2.2431 2.7231 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.4238 4.7896 -0.1188 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.9684 -0.5048 -0.7168 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.0227 4.3878 0.8021 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.1858 4.3160 -1.0291 H 0 0 0 0 0 0 0 0 0 0 0 0 0.4122 3.8810 -0.7210 H 0 0 0 0 0 0 0 0 0 0 0 0 0.5449 3.3815 1.0366 H 0 0 0 0 0 0 0 0 0 0 0 0 1.1355 1.2211 0.5760 H 0 0 0 0 0 0 0 0 0 0 0 0 0.5179 -0.8656 -2.3150 H 0 0 0 0 0 0 0 0 0 0 0 0 3.8861 -0.6627 0.7938 H 0 0 0 0 0 0 0 0 0 0 0 0 6.0572 -1.2389 1.7590 H 0 0 0 0 0 0 0 0 0 0 0 0 7.5640 -2.8384 0.6667 H 0 0 0 0 0 0 0 0 0 0 0 0 6.8781 -3.8734 -1.4261 H 0 0 0 0 0 0 0 0 0 0 0 0 4.6998 -3.3235 -2.4361 H 0 0 0 0 0 0 0 0 0 0 0 0 2.0712 2.3768 -2.8794 H 0 0 0 0 0 0 0 0 0 0 0 0 2.7283 0.6998 -2.4485 H 0 0 0 0 0 0 0 0 0 0 0 0 1.3829 0.9033 -3.5899 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.4593 1.1741 -3.0730 H 0 0 0 0 0 0 0 0 0 0 0 0 2.8378 2.7897 0.5567 H 0 0 0 0 0 0 0 0 0 0 0 0 2.5726 3.2951 -1.1245 H 0 0 0 0 0 0 0 0 0 0 0 0 3.2741 1.6307 -0.7172 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 1 0 3 4 2 0 4 5 1 0 5 6 2 0 6 7 1 0 7 8 2 0 8 9 1 0 9 10 1 0 7 11 1 0 11 12 1 0 6 13 1 0 13 14 2 0 14 15 1 0 15 16 2 0 16 17 1 0 17 18 2 0 18 19 1 0 17 20 1 0 20 21 1 0 21 22 1 0 14 23 1 0 23 24 1 0 24 25 1 0 25 26 1 0 26 27 1 0 27 28 1 0 28 29 2 0 28 30 1 0 30 31 2 0 31 32 1 0 32 33 2 0 33 34 1 0 34 35 2 0 25 36 1 0 25 37 1 6 24 38 1 0 8 3 1 0 18 13 1 0 35 30 1 0 26 5 1 0 22 16 1 0 1 39 1 0 1 40 1 0 1 41 1 0 4 42 1 0 10 43 1 0 10 44 1 0 10 45 1 0 12 46 1 0 12 47 1 0 12 48 1 0 15 49 1 0 19 50 1 0 21 51 1 0 21 52 1 0 23 53 1 0 23 54 1 0 24 55 1 1 26 56 1 6 31 57 1 0 32 58 1 0 33 59 1 0 34 60 1 0 35 61 1 0 36 62 1 0 36 63 1 0 36 64 1 0 37 65 1 0 38 66 1 0 38 67 1 0 38 68 1 0 M END

Standard InCHIKey	VJGNXZQPNWMFAQ-SSEZWIOCSA-N
Standard InCHI	InChI=1S/C29H30O9/c1-15-11-17-12-20-24(37-14-36-20)23(30)21(17)22-18(13-19(33-3)25(34-4)26(22)35-5)27(29(15,2)32)38-28(31)16-9-7-6-8-10-16/h6-10,12-13,15,27,30,32H,11,14H2,1-5H3/t15-,27-,29-/m0/s1
SMILES	COc1cc2c(c(c1OC)OC)c1c(cc3c(c1O)OCO3)C[C@@H]([C@]([C@H]2OC(=O)c1ccccc1)(C)O)C

Calculated Properties

Physi-Chem Properties

Molecular Weight:	522.19	Volume:	520.105 ? Van der Waals volume.
Dense:	1.004	LogP:	3.982 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	3.378 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-5.51 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	6.0	Rigid Bonds:	29.0
TPSA:	112.91 ? Topological Polar Surface Area.	H-Bond Acceptor:	9.0
H-Bond Donor:	2.0	Rings:	5.0
Heavy Atoms:	9.0

MedChem Properties

QED Drug-Likeness Score:	0.462	GASA:	0.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	3.905	Fsp³:	0.345
MCE-18:	104.205 ? 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:	1	PAINS Alert:	0
Colloidal aggregators:	0.444	Fluc inhibitor:	0.104 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.436 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.74 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.052	Promiscuous compounds:	0.158

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.115	MDCK Permeability:	-4.789
Pgp-inhibitor:	0.01	Pgp-substrate:	0.007
PAMPA:	0.751 ? 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%):	0.045	30% Bioavailability (F30%):	0.001
50% Bioavailability (F50%):	0.815

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.066	MRP1:	1.0
Plasma Protein Binding (PPB):	96.546%	Volume Distribution (VD):	0.017
Fu:	2.971% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.974
OATP1B3 inhibitor:	0.981	BCRP inhibitor:	0.018
BSEP inhibitor:	0.996

ADMET: Metabolism

CYP1A2-inhibitor:	0.373	CYP1A2-substrate:	0.947
CYP2C19-inhibitor:	0.994	CYP2C19-substrate:	0.424
CYP2C9-inhibitor:	0.406	CYP2C9-substrate:	0.013
CYP2D6-inhibitor:	0.008	CYP2D6-substrate:	0.779
CYP3A4-inhibitor:	0.999	CYP3A4-substrate:	1.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.979
HLM stability:	0.598 ? 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):

2.779

Half-life (T1/2):

1.164

ADMET: Toxicity

hERG Blockers:	0.208	hERG Blockers (10um):	0.741
Human Hepatotoxicity (H-HT):	0.294	Drug-induced Liver Injury (DILI):	0.908
AMES Toxicity:	0.424	Rat Oral Acute Toxicity:	0.319
Maximum Recommended Daily Dose:	0.761	Skin Sensitization:	0.917
Carcinogencity:	0.946	Eye Corrosion:	0.0
Eye Irritation:	0.429	Respiratory Toxicity:	0.628
Drug-induced Neurotoxicity:	0.848	Ototoxicity:	0.347
Hematotoxicity:	0.16	Drug-induced Nephrotoxicity:	0.848
Genotoxicity:	0.567	RPMI-8226 Immunitoxicity:	0.279
A549 Cytotoxicity:	0.716	Hek293 Cytotoxicity:	0.839
BCF:	1.333 ? 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:	4.101 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.641 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.901 ? 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
NPO33401	schisandra sphenathera	Species	Schisandraceae	Eukaryota	stems	n.a.	n.a.	PMID[23237974]
NPO8367	Fructus schiandrae	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[COCONUT]
NPO25239	Kadsura peltigera	Species	Schisandraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO8367	Fructus schiandrae	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[HerDing]
NPO25239	Kadsura peltigera	Species	Schisandraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO25239	Kadsura peltigera	Species	Schisandraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO8367	Fructus schiandrae	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[TCMID]
NPO25239	Kadsura peltigera	Species	Schisandraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO25239	Kadsura peltigera	Species	Schisandraceae	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	10
Inhibition	8

Activity Type	# Activity
Individual protein	9
Cell line	3
Organism	4
Non-molecular	2

Molecular-level activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1594	Individual protein	Multidrug resistance-associated protein 1	Homo sapiens	IC50	=	0.0004	ug.mL-1	PMID[17129588]
NPT1594	Individual protein	Multidrug resistance-associated protein 1	Homo sapiens	IC50	=	1.597	ug.mL-1	PMID[17129588]
NPT1594	Individual protein	Multidrug resistance-associated protein 1	Homo sapiens	IC50	=	0.0033	ug.mL-1	PMID[17129588]
NPT1594	Individual protein	Multidrug resistance-associated protein 1	Homo sapiens	IC50	=	0.058	ug.mL-1	PMID[17129588]
NPT1594	Individual protein	Multidrug resistance-associated protein 1	Homo sapiens	IC50	=	0.085	ug.mL-1	PMID[17129588]
NPT1594	Individual protein	Multidrug resistance-associated protein 1	Homo sapiens	IC50	=	0.855	ug.mL-1	PMID[17129588]
NPT67	Individual protein	Cholinesterase	Equus caballus	Inhibition	=	-0.32	%	PMID[23062825]
NPT4026	Individual protein	DNA-binding protein inhibitor ID-1	Homo sapiens	Inhibition	=	41.0	%	PMID[23237974]
NPT66	Individual protein	Acetylcholinesterase	Electrophorus electricus	Inhibition	=	5.31	%	PMID[23062825]

In vitro activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT659	Cell line	SMMC-7721	Homo sapiens	IC50	>	100000.0	nM	PMID[23237974]
NPT165	Cell line	HeLa	Homo sapiens	IC50	=	74300.0	nM	PMID[23237974]
NPT71	Cell line	HEK293	Homo sapiens	Inhibition	=	10.9	%	PMID[24018191]
NPT20529	Non-molecular	NON-PROTEIN TARGET	n.a.	IC50	>	100000.0	nM	PMID[23237974]
NPT20529	Non-molecular	NON-PROTEIN TARGET	n.a.	IC50	=	100000.0	nM	PMID[23237974]
NPT963	Organism	Hepatitis B virus	Hepatitis B virus	Inhibition	=	23.9	%	PMID[19640714]
NPT963	Organism	Hepatitis B virus	Hepatitis B virus	Inhibition	=	0.0	%	PMID[19640714]

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
-	Artemia salina	LC50	=	73.5	ug.mL-1	PMID[23237974]

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 NPC88557 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	11434
0.1-0.2	34123
0.2-0.3	4095
0.3-0.4	143
0.4-0.5	31
0.5-0.6	22
0.6-0.7	1
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	Natural Product ID
0.7703	Intermediate Similarity	NPC83049
0.7703	Intermediate Similarity	NPC320471
0.7703	Intermediate Similarity	NPC118162
0.7432	Intermediate Similarity	NPC79322
0.7105	Intermediate Similarity	NPC42797
0.7089	Intermediate Similarity	NPC485504
0.679	Remote Similarity	NPC311912
0.5714	Remote Similarity	NPC291977
0.557	Remote Similarity	NPC252286
0.5541	Remote Similarity	NPC184684
0.5541	Remote Similarity	NPC184641
0.5529	Remote Similarity	NPC483405
0.5309	Remote Similarity	NPC121661
0.5301	Remote Similarity	NPC473445
0.5294	Remote Similarity	NPC475756
0.5294	Remote Similarity	NPC280778
0.5244	Remote Similarity	NPC191352
0.5238	Remote Similarity	NPC126405
0.5238	Remote Similarity	NPC53669
0.5238	Remote Similarity	NPC77237
0.5238	Remote Similarity	NPC297271
0.5238	Remote Similarity	NPC224472
0.5238	Remote Similarity	NPC16791
0.5238	Remote Similarity	NPC217708
0.5172	Remote Similarity	NPC474606
0.5114	Remote Similarity	NPC29727
0.5109	Remote Similarity	NPC230531
0.5062	Remote Similarity	NPC73467
0.5059	Remote Similarity	NPC258322

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC88557 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	2567
0.1-0.2	6378
0.2-0.3	205
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