NPASS Compound

Natural Product: NPC143480

Natural Product ID	NPC143480
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	Lapathoside B
IUPAC Name	[(2S,3S,4R,5R)-4-hydroxy-2,5-bis[[(E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoyl]oxymethyl]-2-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-[[(E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoyl]oxymethyl]oxan-2-yl]oxyoxolan-3-yl] (E)-3-(4-hydroxyphenyl)prop-2-enoate
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL505183
PubChem CID	11147473
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000476] Cinnamic acids and derivatives [CHEMONTID:0001391] Hydroxycinnamic acids and derivatives [CHEMONTID:0003002] Hydroxycinnamic acid esters [CHEMONTID:0000465] Coumaric acid esters

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

Chemical Representations

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0 0 0 -5.2301 -15.9151 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0810 -16.8793 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9319 -17.8434 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.1924 -19.3207 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.6019 -19.8337 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.0433 -20.2848 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3038 -21.7620 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1547 -22.7262 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4152 -24.2034 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2661 -25.1676 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1434 -24.6546 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4039 -23.1774 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2548 -22.2132 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8134 -22.6644 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.0739 -21.1871 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2925 -25.6188 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.1510 -14.8731 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.1164 -16.6016 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.7904 -13.6290 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.6291 -14.8726 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.1408 -16.2909 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -10.1255 -14.7679 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -10.9643 -16.0115 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -12.4606 -15.9069 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -13.2994 -17.1504 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -14.7958 -17.0458 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -15.4533 -15.6976 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -14.6145 -14.4540 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -13.1182 -14.5587 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -16.9497 -15.5930 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.5800 -13.0119 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8296 -10.5705 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.5800 -8.1291 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.0490 -0.5490 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 2.4510 -2.0490 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 4.5000 -2.5981 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 1.5000 -2.5981 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0000 -0.0000 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.5000 2.5981 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 3.0000 2.5981 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0000 -2.5981 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 0.7500 -3.8971 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.7337 -8.0139 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.7990 -7.0442 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.3991 -8.1291 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 0.6595 -9.6063 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 0.1700 -12.3825 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.4791 -13.3467 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.5940 -11.1717 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.8471 -11.3652 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.6603 -12.2522 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.2601 -7.7031 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.8600 -9.3736 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.6230 -6.2477 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.3488 -3.3368 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -11.6648 -7.5047 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -14.2089 -3.5013 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -11.3531 -2.6008 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -13.1164 -1.6830 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -11.6133 -1.9238 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.5287 -12.2521 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.0536 -15.1586 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.0688 -17.1586 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.1168 -15.7302 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.0452 -18.0283 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.6338 -19.7718 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.7133 -22.2751 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.8247 -24.7165 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.5266 -26.6448 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 0.5153 -20.7360 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 4.5511 -21.4476 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 1.5967 -20.9267 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 3.3344 -19.7099 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 3.7020 -25.1057 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.5653 -16.9899 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.7830 -13.4198 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.3067 -17.3597 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -12.6419 -18.4986 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -15.6345 -18.2893 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -15.2721 -13.1059 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -12.2794 -13.3151 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1 75 1 0 1 76 1 0 4 77 1 0 6 78 1 0 7 79 1 0 9 80 1 0 10 81 1 0 11 82 1 0 15 83 1 0 15 84 1 0 16 85 1 1 17 86 1 6 18 87 1 1 19 88 1 6 20 89 1 6 24 90 1 0 24 91 1 0 28 92 1 0 29 93 1 0 31 94 1 0 32 95 1 0 35 96 1 0 37 97 1 0 37 98 1 0 37 99 1 0 38100 1 0 39101 1 1 40102 1 6 41103 1 1 42104 1 0 42105 1 0 46106 1 0 47107 1 0 49108 1 0 50109 1 0 53110 1 0 55111 1 0 55112 1 0 55113 1 0 56114 1 0 58115 1 0 62116 1 0 63117 1 0 65118 1 0 66119 1 0 68120 1 0 69121 1 0 70122 1 0 71123 1 0 72124 1 0 73125 1 0 M END

Standard InCHIKey	IZEAEHCVLNYCTN-WGWFIJCNSA-N
Standard InCHI	InChI=1S/C51H52O22/c1-64-36-22-29(6-15-33(36)53)10-18-41(56)67-25-39-45(60)47(62)48(63)50(70-39)73-51(27-69-43(58)20-12-31-8-17-35(55)38(24-31)66-3)49(71-44(59)21-9-28-4-13-32(52)14-5-28)46(61)40(72-51)26-68-42(57)19-11-30-7-16-34(54)37(23-30)65-2/h4-24,39-40,45-50,52-55,60-63H,25-27H2,1-3H3/b18-10+,19-11+,20-12+,21-9+/t39-,40-,45-,46-,47+,48-,49+,50-,51+/m1/s1
SMILES	COc1cc(ccc1O)/C=C/C(=O)OC[C@@H]1[C@H]([C@@H]([C@H]([C@H](O1)O[C@@]1(COC(=O)/C=C/c2ccc(c(c2)OC)O)[C@H]([C@@H]([C@@H](COC(=O)/C=C/c2ccc(c(c2)OC)O)O1)O)OC(=O)/C=C/c1ccc(cc1)O)O)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	1016.3	Volume:	979.969 ? Van der Waals volume.
Dense:	1.037	LogP:	2.363 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	2.302 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.04 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	24.0	Rigid Bonds:	43.0
TPSA:	322.42 ? Topological Polar Surface Area.	H-Bond Acceptor:	22.0
H-Bond Donor:	8.0	Rings:	6.0
Heavy Atoms:	22.0

MedChem Properties

QED Drug-Likeness Score:	0.036	GASA:	0.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.546	Fsp³:	0.294
MCE-18:	144.0 ? 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:	0
Colloidal aggregators:	0.995	Fluc inhibitor:	1.0 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.246 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.665 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.138	Promiscuous compounds:	0.193

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-6.15	MDCK Permeability:	-5.393
Pgp-inhibitor:	0.956	Pgp-substrate:	0.002
PAMPA:	0.342 ? 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):	0.085
20% Bioavailability (F20%):	0.999	30% Bioavailability (F30%):	1.0
50% Bioavailability (F50%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.0
Plasma Protein Binding (PPB):	87.9%	Volume Distribution (VD):	-0.407
Fu:	10.387% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.079
BSEP inhibitor:	1.0

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.445
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.986
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.023
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.855
CYP3A4-inhibitor:	0.0	CYP3A4-substrate:	1.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	1.0
HLM stability:	0.764 ? 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):

1.607

Half-life (T1/2):

4.145

ADMET: Toxicity

hERG Blockers:	0.142	hERG Blockers (10um):	0.77
Human Hepatotoxicity (H-HT):	0.355	Drug-induced Liver Injury (DILI):	0.792
AMES Toxicity:	0.882	Rat Oral Acute Toxicity:	0.015
Maximum Recommended Daily Dose:	0.82	Skin Sensitization:	1.0
Carcinogencity:	0.014	Eye Corrosion:	0.0
Eye Irritation:	0.004	Respiratory Toxicity:	0.006
Drug-induced Neurotoxicity:	0.073	Ototoxicity:	0.893
Hematotoxicity:	0.017	Drug-induced Nephrotoxicity:	0.853
Genotoxicity:	0.334	RPMI-8226 Immunitoxicity:	0.511
A549 Cytotoxicity:	0.73	Hek293 Cytotoxicity:	0.962
BCF:	0.409 ? 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:	3.653 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.046 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.604 ? 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
NPO7193	Persicaria lapathifolia	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11678656]
NPO7193	Persicaria lapathifolia	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO7193	Persicaria lapathifolia	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO7193	Persicaria lapathifolia	Species	Polygonaceae	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
Activity	8

Activity Type	# Activity
Cell line	4
Others	4

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
NPT80	Cell line	Raji	Homo sapiens	Activity	=	60.0	%	PMID[11678656]
NPT80	Cell line	Raji	Homo sapiens	Activity	>	80.0	%	PMID[11678656]
NPT2	Others	Unspecified	n.a.	Activity	=	26.8	%	PMID[11678656]
NPT2	Others	Unspecified	n.a.	Activity	=	51.6	%	PMID[11678656]
NPT2	Others	Unspecified	n.a.	Activity	=	77.9	%	PMID[11678656]
NPT2	Others	Unspecified	n.a.	Activity	=	100.0	%	PMID[11678656]

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 NPC143480 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	13778
0.1-0.2	30849
0.2-0.3	4233
0.3-0.4	773
0.4-0.5	161
0.5-0.6	39
0.6-0.7	13
0.7-0.8	0
0.8-0.85	1
0.85-0.9	0
0.9-0.95	1
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC125823
1.0	High Similarity	NPC7145
0.9625	High Similarity	NPC201148
0.9136	High Similarity	NPC3460
0.8313	Intermediate Similarity	NPC300262
0.7816	Intermediate Similarity	NPC85192
0.7778	Intermediate Similarity	NPC28637
0.7727	Intermediate Similarity	NPC215095
0.7241	Intermediate Similarity	NPC83743
0.7126	Intermediate Similarity	NPC262182
0.6915	Remote Similarity	NPC28651
0.6782	Remote Similarity	NPC226005
0.6667	Remote Similarity	NPC472612
0.6632	Remote Similarity	NPC261122
0.6421	Remote Similarity	NPC472611
0.6413	Remote Similarity	NPC80732
0.6322	Remote Similarity	NPC225307
0.6222	Remote Similarity	NPC476869
0.6211	Remote Similarity	NPC287615
0.6211	Remote Similarity	NPC199311
0.6154	Remote Similarity	NPC90896
0.6154	Remote Similarity	NPC471881
0.6082	Remote Similarity	NPC210611
0.5895	Remote Similarity	NPC216819
0.5851	Remote Similarity	NPC476865
0.5833	Remote Similarity	NPC283839
0.5684	Remote Similarity	NPC289967
0.567	Remote Similarity	NPC192763
0.567	Remote Similarity	NPC11411
0.5652	Remote Similarity	NPC35288
0.5648	Remote Similarity	NPC484988
0.5638	Remote Similarity	NPC476868
0.5543	Remote Similarity	NPC291296
0.5532	Remote Similarity	NPC471882
0.5532	Remote Similarity	NPC476866
0.5484	Remote Similarity	NPC45224
0.5484	Remote Similarity	NPC471405
0.5402	Remote Similarity	NPC479473
0.5402	Remote Similarity	NPC275721
0.5402	Remote Similarity	NPC288416
0.5402	Remote Similarity	NPC479468
0.5402	Remote Similarity	NPC479474
0.5385	Remote Similarity	NPC219677
0.5376	Remote Similarity	NPC10205
0.5357	Remote Similarity	NPC157554
0.5333	Remote Similarity	NPC34293
0.5294	Remote Similarity	NPC600370
0.5253	Remote Similarity	NPC488081
0.5248	Remote Similarity	NPC173343
0.5234	Remote Similarity	NPC479771
0.5222	Remote Similarity	NPC291153
0.5169	Remote Similarity	NPC246024
0.5167	Remote Similarity	NPC601579
0.5161	Remote Similarity	NPC252833
0.5155	Remote Similarity	NPC488082
0.5152	Remote Similarity	NPC479767
0.5149	Remote Similarity	NPC133984
0.5114	Remote Similarity	NPC470572
0.5104	Remote Similarity	NPC157816
0.5054	Remote Similarity	NPC252114
0.5053	Remote Similarity	NPC281798
0.5049	Remote Similarity	NPC7191

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC143480 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	4418
0.1-0.2	4642
0.2-0.3	86
0.3-0.4	3
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