NPASS Compound

Natural Product: NPC475484

Natural Product ID	NPC475484
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	Arbortristoside B
IUPAC Name	methyl (1S,4aS,5S,6R,7S,7aS)-6-[(E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy-5-hydroxy-7-(hydroxymethyl)-1-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-1,4a,5,6,7,7a-hexahydrocyclopenta[c]pyran-4-carboxylate
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL506451
PubChem CID	44576088
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0002049] Terpene glycosides [CHEMONTID:0004081] Iridoid O-glycosides

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 73 76 0 0 0 0 0 0 0 0999 V2000 -0.4107 2.0928 -1.0487 O 0 0 0 0 0 0 0 0 0 0 0 0 0.6396 1.1964 -0.8727 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2289 -0.2337 -1.1449 C 0 0 1 0 0 0 0 0 0 0 0 0 1.3327 -1.2103 -0.9647 C 0 0 1 0 0 0 0 0 0 0 0 0 2.5873 -0.6545 -0.7107 O 0 0 0 0 0 0 0 0 0 0 0 0 3.7011 -0.7808 -1.4946 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6303 -1.4420 -2.5349 O 0 0 0 0 0 0 0 0 0 0 0 0 4.9444 -0.1147 -1.0552 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0055 0.5826 0.0488 C 0 0 0 0 0 0 0 0 0 0 0 0 6.2001 1.2604 0.5325 C 0 0 0 0 0 0 0 0 0 0 0 0 6.1453 1.9790 1.7323 C 0 0 0 0 0 0 0 0 0 0 0 0 7.2536 2.6327 2.2212 C 0 0 0 0 0 0 0 0 0 0 0 0 8.4652 2.6169 1.5650 C 0 0 0 0 0 0 0 0 0 0 0 0 8.5306 1.9139 0.3850 C 0 0 0 0 0 0 0 0 0 0 0 0 7.4105 1.2461 -0.1207 C 0 0 0 0 0 0 0 0 0 0 0 0 9.7411 1.8843 -0.2933 O 0 0 0 0 0 0 0 0 0 0 0 0 9.5870 3.2723 2.0497 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8864 -2.2289 0.0346 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.6239 -2.1350 0.0130 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8900 -0.6851 -0.2478 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.1993 -0.4330 -0.9805 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.1664 -1.2291 -2.1918 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.8796 -2.5899 -2.0815 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1539 -3.0050 -1.0392 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9214 -4.4612 -0.9944 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3604 -5.2477 -1.8706 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.1952 -5.0094 0.0444 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0196 -6.4002 0.0787 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3107 -0.7096 -0.2241 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.1070 0.4192 -0.1070 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.1824 0.8157 1.2238 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.6804 2.0925 1.3494 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.5020 2.1678 2.6219 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.5639 1.2725 2.6014 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.4212 2.6010 0.1680 C 0 0 2 0 0 0 0 0 0 0 0 0 -6.1739 1.5693 -0.6055 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.5015 0.2152 -0.6048 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.5532 -0.3951 -1.8520 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.5128 1.4824 -0.2319 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.6007 3.3875 -0.6744 O 0 0 0 0 0 0 0 0 0 0 0 0 1.3101 -1.9831 1.3263 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.5577 2.3563 -1.9722 H 0 0 0 0 0 0 0 0 0 0 0 0 0.9501 1.3186 0.2059 H 0 0 0 0 0 0 0 0 0 0 0 0 1.4378 1.4766 -1.5651 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.1731 -0.2239 -2.1948 H 0 0 0 0 0 0 0 0 0 0 0 0 1.4440 -1.7673 -1.9293 H 0 0 0 0 0 0 0 0 0 0 0 0 5.8253 -0.2116 -1.6705 H 0 0 0 0 0 0 0 0 0 0 0 0 4.0857 0.6512 0.6382 H 0 0 0 0 0 0 0 0 0 0 0 0 5.2207 2.0168 2.2751 H 0 0 0 0 0 0 0 0 0 0 0 0 7.1997 3.1918 3.1609 H 0 0 0 0 0 0 0 0 0 0 0 0 7.5037 0.7075 -1.0472 H 0 0 0 0 0 0 0 0 0 0 0 0 10.5086 1.3836 0.1543 H 0 0 0 0 0 0 0 0 0 0 0 0 9.7758 3.3734 3.0448 H 0 0 0 0 0 0 0 0 0 0 0 0 1.2144 -3.2538 -0.2160 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0230 -2.4436 1.0237 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.9396 -0.0986 0.6940 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.1791 0.6168 -1.3275 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.2592 -3.2389 -2.8449 H 0 0 0 0 0 0 0 0 0 0 0 0 0.9584 -6.5721 0.6450 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.8121 -6.8917 0.6027 H 0 0 0 0 0 0 0 0 0 0 0 0 0.1510 -6.8395 -0.9356 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.6376 1.2590 -0.6586 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.7954 2.7683 1.5120 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.9186 3.2093 2.6514 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.8939 1.9938 3.5123 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.8192 1.1132 3.5418 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.1902 3.3364 0.5523 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.1863 1.9041 -1.6831 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.0953 -0.4294 0.0837 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.7745 -1.3578 -1.7751 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.8742 2.3998 -0.2148 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.4135 4.2624 -0.2434 H 0 0 0 0 0 0 0 0 0 0 0 0 0.5585 -1.7631 1.9301 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 1 0 3 4 1 0 4 5 1 0 5 6 1 0 6 7 2 0 6 8 1 0 8 9 2 0 9 10 1 0 10 11 2 0 11 12 1 0 12 13 2 0 13 14 1 0 14 15 2 0 14 16 1 0 13 17 1 0 4 18 1 0 18 19 1 0 19 20 1 0 20 21 1 0 21 22 1 0 22 23 1 0 23 24 2 0 24 25 1 0 25 26 2 0 25 27 1 0 27 28 1 0 21 29 1 0 29 30 1 0 30 31 1 0 31 32 1 0 32 33 1 0 33 34 1 0 32 35 1 0 35 36 1 0 36 37 1 0 37 38 1 0 36 39 1 0 35 40 1 0 18 41 1 0 20 3 1 0 37 30 1 0 15 10 1 0 24 19 1 0 1 42 1 0 2 43 1 0 2 44 1 0 3 45 1 6 4 46 1 6 8 47 1 0 9 48 1 0 11 49 1 0 12 50 1 0 15 51 1 0 16 52 1 0 17 53 1 0 18 54 1 6 19 55 1 1 20 56 1 1 21 57 1 6 23 58 1 0 28 59 1 0 28 60 1 0 28 61 1 0 30 62 1 6 32 63 1 1 33 64 1 0 33 65 1 0 34 66 1 0 35 67 1 1 36 68 1 6 37 69 1 1 38 70 1 0 39 71 1 0 40 72 1 0 41 73 1 0 M END

Standard InCHIKey	PSFREQJZNFIHKK-OKPJLNDISA-N
Standard InCHI	InChI=1S/C26H32O15/c1-37-24(36)12-9-38-25(41-26-22(35)21(34)19(32)15(8-28)39-26)18-11(7-27)23(20(33)17(12)18)40-16(31)5-3-10-2-4-13(29)14(30)6-10/h2-6,9,11,15,17-23,25-30,32-35H,7-8H2,1H3/b5-3+/t11-,15-,17-,18-,19-,20+,21+,22-,23-,25+,26+/m1/s1
SMILES	OC[C@H]1[C@@H](OC(=O)/C=C/c2ccc(c(c2)O)O)[C@H]([C@H]2[C@@H]1[C@@H](OC=C2C(=O)OC)O[C@@H]1O[C@H](CO)[C@H]([C@@H]([C@H]1O)O)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	584.17	Volume:	537.424 ? Van der Waals volume.
Dense:	1.087	LogP:	0.031 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	0.642 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-2.258 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	10.0	Rigid Bonds:	25.0
TPSA:	242.13 ? Topological Polar Surface Area.	H-Bond Acceptor:	15.0
H-Bond Donor:	8.0	Rings:	4.0
Heavy Atoms:	15.0

MedChem Properties

QED Drug-Likeness Score:	0.089	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.091	Fsp³:	0.538
MCE-18:	102.95 ? MCE-18 stands for medicinal chemistry evolution.MCE-18≥45 is considered a suitable value.	Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected	GSK Rule:	Accepted
Golden Triangle Rule:	Accepted	BMS Rule:	0
Chelating Alert:	1	PAINS Alert:	1
Colloidal aggregators:	0.813	Fluc inhibitor:	0.66 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.31 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.22 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.18	Promiscuous compounds:	0.318

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-6.445	MDCK Permeability:	-5.217
Pgp-inhibitor:	0.0	Pgp-substrate:	0.035
PAMPA:	0.997 ? 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):	0.677
20% Bioavailability (F20%):	0.922	30% Bioavailability (F30%):	0.999
50% Bioavailability (F50%):	0.999

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.164
Plasma Protein Binding (PPB):	55.831%	Volume Distribution (VD):	-0.48
Fu:	44.249% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.007
BSEP inhibitor:	0.002

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.0
CYP3A4-inhibitor:	0.0	CYP3A4-substrate:	0.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.997
HLM stability:	0.002 ? 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):

2.107

Half-life (T1/2):

3.275

ADMET: Toxicity

hERG Blockers:	0.01	hERG Blockers (10um):	0.103
Human Hepatotoxicity (H-HT):	0.585	Drug-induced Liver Injury (DILI):	0.939
AMES Toxicity:	0.86	Rat Oral Acute Toxicity:	0.007
Maximum Recommended Daily Dose:	0.017	Skin Sensitization:	1.0
Carcinogencity:	0.069	Eye Corrosion:	0.0
Eye Irritation:	0.115	Respiratory Toxicity:	0.002
Drug-induced Neurotoxicity:	0.002	Ototoxicity:	0.995
Hematotoxicity:	0.154	Drug-induced Nephrotoxicity:	0.787
Genotoxicity:	0.475	RPMI-8226 Immunitoxicity:	0.03
A549 Cytotoxicity:	0.668	Hek293 Cytotoxicity:	0.146
BCF:	0.449 ? 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:	3.189 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.033 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.136 ? 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
NPO33172	nyctanthes arbortristis	Species	Oleaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[1791475]
NPO33172	nyctanthes arbortristis	Species	Oleaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22608855]

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
Inhibition	12
Activity	6
IC50	2
Survival	1

Activity Type	# Activity
Individual protein	8
Cell line	2
Organism	11

Molecular-level activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT6376	Individual protein	Trypanothione reductase	Leishmania donovani	Inhibition	=	46.87	%	PMID[16562829]
NPT6376	Individual protein	Trypanothione reductase	Leishmania donovani	Inhibition	=	67.87	%	PMID[17503850]
NPT6376	Individual protein	Trypanothione reductase	Leishmania donovani	Inhibition	=	77.53	%	PMID[16038539]
NPT6376	Individual protein	Trypanothione reductase	Leishmania donovani	Inhibition	=	96.88	%	PMID[16038539]
NPT6376	Individual protein	Trypanothione reductase	Leishmania donovani	Inhibition	=	41.87	%	PMID[23570615]
NPT6376	Individual protein	Trypanothione reductase	Leishmania donovani	Inhibition	=	63.63	%	PMID[22085418]
NPT6376	Individual protein	Trypanothione reductase	Leishmania donovani	Inhibition	=	92.58	%	PMID[17503850]

In vitro activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT71	Cell line	HEK293	Homo sapiens	Activity	=	54.83	%	PMID[20606069]
NPT71	Cell line	HEK293	Homo sapiens	Activity	=	93.62	%	DOI[10.1016/0305-1978(94)90001-9]
NPT633	Organism	Leishmania donovani	Leishmania donovani	Inhibition	=	28.13	%	PMID[25464882]
NPT633	Organism	Leishmania donovani	Leishmania donovani	Inhibition	=	41.74	%	PMID[25464882]
NPT633	Organism	Leishmania donovani	Leishmania donovani	Inhibition	=	25.12	%	PMID[25464882]
NPT633	Organism	Leishmania donovani	Leishmania donovani	Inhibition	=	47.34	%	PMID[3404149]
NPT633	Organism	Leishmania donovani	Leishmania donovani	IC50	=	7630.0	nM	PubChem BioAssay data set
NPT633	Organism	Leishmania donovani	Leishmania donovani	IC50	=	3504.0	nM	PMID[23571415]
NPT633	Organism	Leishmania donovani	Leishmania donovani	Activity	=	2.96	%	PMID[25237727]
NPT633	Organism	Leishmania donovani	Leishmania donovani	Activity	=	13.52	%	PMID[25237727]
NPT633	Organism	Leishmania donovani	Leishmania donovani	Activity	=	31.04	%	PMID[25237727]
NPT633	Organism	Leishmania donovani	Leishmania donovani	Activity	=	52.48	%	PMID[25237727]

In vivo activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT633	Organism	Leishmania donovani	Leishmania donovani	Survival	=	59.0	day	PMID[6481359]

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 NPC475484 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	13218
0.1-0.2	32223
0.2-0.3	3591
0.3-0.4	650
0.4-0.5	151
0.5-0.6	12
0.6-0.7	7
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
0.7875	Intermediate Similarity	NPC96599
0.7024	Intermediate Similarity	NPC475379
0.6364	Remote Similarity	NPC31745
0.6364	Remote Similarity	NPC220936
0.6111	Remote Similarity	NPC202391
0.6111	Remote Similarity	NPC296659
0.6087	Remote Similarity	NPC240592
0.6087	Remote Similarity	NPC117346
0.6022	Remote Similarity	NPC203664
0.5789	Remote Similarity	NPC63304
0.5733	Remote Similarity	NPC232880
0.5714	Remote Similarity	NPC475213
0.5714	Remote Similarity	NPC152796
0.5663	Remote Similarity	NPC477294
0.5435	Remote Similarity	NPC18789
0.5408	Remote Similarity	NPC69367
0.5375	Remote Similarity	NPC475928
0.5319	Remote Similarity	NPC486495
0.5294	Remote Similarity	NPC477293
0.525	Remote Similarity	NPC474730
0.525	Remote Similarity	NPC170432

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC475484 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	5458
0.1-0.2	3623
0.2-0.3	66
0.3-0.4	2
0.4-0.5	1
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