NPASS Compound

Natural Product: NPC225307

Natural Product ID	NPC225307
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	Lapathoside D
IUPAC Name	[(2R,3R,4S,5S)-3-hydroxy-5-(hydroxymethyl)-4-[(E)-3-(4-hydroxyphenyl)prop-2-enoyl]oxy-5-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxolan-2-yl]methyl (E)-3-(4-hydroxyphenyl)prop-2-enoate
Synonyms	Lapathoside D
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL508200
PubChem CID	10077800
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

RDKit 3D 79 82 0 0 0 0 0 0 0 0999 V2000 -1.9600 -4.9784 -2.5994 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.8704 -4.4514 -1.6674 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2437 -4.3652 -0.2867 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.1336 -3.5651 -0.2599 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.4493 -2.1935 -0.3605 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.2616 -1.5144 -0.3094 O 0 0 0 0 0 0 0 0 0 0 0 0 0.1627 -0.9458 -1.5073 C 0 0 2 0 0 0 0 0 0 0 0 0 0.4253 -2.0168 -2.5491 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8217 -1.3923 -3.7185 O 0 0 0 0 0 0 0 0 0 0 0 0 1.3691 -0.3263 -1.2174 O 0 0 0 0 0 0 0 0 0 0 0 0 1.6347 0.6398 -2.1451 C 0 0 1 0 0 0 0 0 0 0 0 0 0.3125 1.1551 -2.6104 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.6924 0.1585 -2.0169 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.5031 0.7904 -1.0660 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.8474 0.9874 -1.2460 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4120 0.5992 -2.2937 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.6160 1.6534 -0.2070 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.9139 1.8350 -0.3961 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.8008 2.4882 0.5649 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.3417 2.9777 1.7626 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.1915 3.5875 2.6547 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.5221 3.7041 2.3324 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.9831 3.2139 1.1325 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.1472 2.6010 0.2280 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.4050 4.3219 3.2274 O 0 0 0 0 0 0 0 0 0 0 0 0 0.2870 1.1533 -3.9951 O 0 0 0 0 0 0 0 0 0 0 0 0 2.4397 1.7500 -1.4550 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6463 1.2064 -0.9431 O 0 0 0 0 0 0 0 0 0 0 0 0 4.5788 1.9784 -0.2705 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3319 3.2012 -0.1182 O 0 0 0 0 0 0 0 0 0 0 0 0 5.8193 1.4173 0.2564 C 0 0 0 0 0 0 0 0 0 0 0 0 6.7159 2.1221 0.8921 C 0 0 0 0 0 0 0 0 0 0 0 0 7.9665 1.6355 1.4416 C 0 0 0 0 0 0 0 0 0 0 0 0 8.8227 2.4813 2.0824 C 0 0 0 0 0 0 0 0 0 0 0 0 10.0176 2.0421 2.6137 C 0 0 0 0 0 0 0 0 0 0 0 0 10.3832 0.7177 2.5097 C 0 0 0 0 0 0 0 0 0 0 0 0 9.5350 -0.1491 1.8685 C 0 0 0 0 0 0 0 0 0 0 0 0 8.3271 0.3117 1.3351 C 0 0 0 0 0 0 0 0 0 0 0 0 11.5718 0.2245 3.0256 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.3303 -1.7517 0.7565 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.7599 -2.9353 1.6218 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.3255 -3.9651 0.6659 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.7329 -5.0566 1.4431 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.7424 -2.4917 2.4905 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7756 -0.7529 1.5646 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.1482 -4.6160 -3.5112 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.7247 -5.1640 -1.6573 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.2260 -3.4743 -2.0210 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.9212 -5.3942 -0.0248 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.8830 -2.0847 -1.3748 H 0 0 0 0 0 0 0 0 0 0 0 0 1.2611 -2.6821 -2.2453 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.4496 -2.6839 -2.6953 H 0 0 0 0 0 0 0 0 0 0 0 0 0.6812 -1.9393 -4.5288 H 0 0 0 0 0 0 0 0 0 0 0 0 2.2287 0.2566 -3.0140 H 0 0 0 0 0 0 0 0 0 0 0 0 0.1007 2.1632 -2.1874 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.3557 -0.1388 -2.8652 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.1483 1.9964 0.7031 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.3422 1.4736 -1.3271 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.3016 2.8873 2.0155 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.7734 3.9539 3.5825 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.0327 3.3054 0.8779 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.4846 2.2096 -0.7165 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.6477 5.3025 3.0417 H 0 0 0 0 0 0 0 0 0 0 0 0 1.2015 1.2507 -4.3941 H 0 0 0 0 0 0 0 0 0 0 0 0 2.7262 2.4954 -2.2248 H 0 0 0 0 0 0 0 0 0 0 0 0 1.8310 2.2596 -0.6925 H 0 0 0 0 0 0 0 0 0 0 0 0 5.9938 0.3635 0.1069 H 0 0 0 0 0 0 0 0 0 0 0 0 6.4819 3.1908 1.0133 H 0 0 0 0 0 0 0 0 0 0 0 0 8.5457 3.5218 2.1694 H 0 0 0 0 0 0 0 0 0 0 0 0 10.6804 2.7291 3.1171 H 0 0 0 0 0 0 0 0 0 0 0 0 9.7751 -1.2156 1.7561 H 0 0 0 0 0 0 0 0 0 0 0 0 7.6991 -0.4163 0.8410 H 0 0 0 0 0 0 0 0 0 0 0 0 11.8541 0.5010 3.9647 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.2749 -1.3490 0.3450 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.8429 -3.2882 2.1386 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.1936 -3.4881 0.1669 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.2089 -5.7412 0.9009 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.9902 -3.1818 3.1506 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.3187 -1.1063 2.3577 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 7 6 1 1 7 8 1 0 8 9 1 0 7 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 2 0 15 17 1 0 17 18 2 0 18 19 1 0 19 20 2 0 20 21 1 0 21 22 2 0 22 23 1 0 23 24 2 0 22 25 1 0 12 26 1 0 11 27 1 0 27 28 1 0 28 29 1 0 29 30 2 0 29 31 1 0 31 32 2 0 32 33 1 0 33 34 2 0 34 35 1 0 35 36 2 0 36 37 1 0 37 38 2 0 36 39 1 0 5 40 1 0 40 41 1 0 41 42 1 0 42 43 1 0 41 44 1 0 40 45 1 0 42 3 1 0 13 7 1 0 24 19 1 0 38 33 1 0 1 46 1 0 2 47 1 0 2 48 1 0 3 49 1 1 5 50 1 6 8 51 1 0 8 52 1 0 9 53 1 0 11 54 1 6 12 55 1 1 13 56 1 6 17 57 1 0 18 58 1 0 20 59 1 0 21 60 1 0 23 61 1 0 24 62 1 0 25 63 1 0 26 64 1 0 27 65 1 0 27 66 1 0 31 67 1 0 32 68 1 0 34 69 1 0 35 70 1 0 37 71 1 0 38 72 1 0 39 73 1 0 40 74 1 6 41 75 1 1 42 76 1 6 43 77 1 0 44 78 1 0 45 79 1 0 M END

Standard InCHIKey	BZSLWPMWZXMHEW-JSCCKXNGSA-N
Standard InCHI	InChI=1S/C30H34O15/c31-13-20-24(37)26(39)27(40)29(42-20)45-30(15-32)28(43-23(36)12-6-17-3-9-19(34)10-4-17)25(38)21(44-30)14-41-22(35)11-5-16-1-7-18(33)8-2-16/h1-12,20-21,24-29,31-34,37-40H,13-15H2/b11-5+,12-6+/t20-,21-,24-,25-,26+,27-,28+,29-,30+/m1/s1
SMILES	OC[C@H]1O[C@H](O[C@]2(CO)O[C@@H]([C@H]([C@@H]2OC(=O)/C=C/c2ccc(cc2)O)O)COC(=O)/C=C/c2ccc(cc2)O)[C@@H]([C@H]([C@@H]1O)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	634.19	Volume:	598.699 ? Van der Waals volume.
Dense:	1.059	LogP:	1.065 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	1.468 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-2.985 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	13.0	Rigid Bonds:	27.0
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:	0.104	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.764	Fsp³:	0.4
MCE-18:	99.429 ? 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:	0	PAINS Alert:	0
Colloidal aggregators:	0.728	Fluc inhibitor:	0.668 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.252 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.634 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.416	Promiscuous compounds:	0.333

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-6.392	MDCK Permeability:	-5.198
Pgp-inhibitor:	0.001	Pgp-substrate:	0.017
PAMPA:	0.999 ? 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):	0.301
20% Bioavailability (F20%):	0.964	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):	80.607%	Volume Distribution (VD):	-0.207
Fu:	20.204% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.0
BSEP inhibitor:	0.704

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.106
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.001
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.012
CYP3A4-inhibitor:	0.0	CYP3A4-substrate:	0.736
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	1.0
HLM stability:	0.026 ? 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):

1.379

Half-life (T1/2):

3.043

ADMET: Toxicity

hERG Blockers:	0.06	hERG Blockers (10um):	0.475
Human Hepatotoxicity (H-HT):	0.574	Drug-induced Liver Injury (DILI):	0.823
AMES Toxicity:	0.841	Rat Oral Acute Toxicity:	0.03
Maximum Recommended Daily Dose:	0.407	Skin Sensitization:	1.0
Carcinogencity:	0.03	Eye Corrosion:	0.0
Eye Irritation:	0.241	Respiratory Toxicity:	0.01
Drug-induced Neurotoxicity:	0.129	Ototoxicity:	0.896
Hematotoxicity:	0.057	Drug-induced Nephrotoxicity:	0.66
Genotoxicity:	0.697	RPMI-8226 Immunitoxicity:	0.152
A549 Cytotoxicity:	0.327	Hek293 Cytotoxicity:	0.747
BCF:	0.581 ? 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:	3.318 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.096 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.383 ? 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
IC50	1

Activity Type	# Activity
Cell line	5
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	=	70.0	%	PMID[11678656]
NPT80	Cell line	Raji	Homo sapiens	Activity	>	80.0	%	PMID[11678656]
NPT165	Cell line	HeLa	Homo sapiens	IC50	>	100000.0	nM	PMID[22542106]
NPT2	Others	Unspecified	n.a.	Activity	=	10.5	%	PMID[11678656]
NPT2	Others	Unspecified	n.a.	Activity	=	38.3	%	PMID[11678656]
NPT2	Others	Unspecified	n.a.	Activity	=	71.4	%	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 NPC225307 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	13004
0.1-0.2	31238
0.2-0.3	4579
0.3-0.4	818
0.4-0.5	158
0.5-0.6	37
0.6-0.7	20
0.7-0.8	0
0.8-0.85	2
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.8082	Intermediate Similarity	NPC28637
0.8026	Intermediate Similarity	NPC262182
0.7722	Intermediate Similarity	NPC300262
0.7024	Intermediate Similarity	NPC3460
0.6835	Remote Similarity	NPC472612
0.6829	Remote Similarity	NPC83743
0.6591	Remote Similarity	NPC261122
0.6548	Remote Similarity	NPC80732
0.6463	Remote Similarity	NPC90896
0.6322	Remote Similarity	NPC125823
0.6322	Remote Similarity	NPC7145
0.6322	Remote Similarity	NPC143480
0.625	Remote Similarity	NPC52097
0.6203	Remote Similarity	NPC219677
0.6176	Remote Similarity	NPC11724
0.6173	Remote Similarity	NPC156692
0.6163	Remote Similarity	NPC216819
0.6136	Remote Similarity	NPC287615
0.6136	Remote Similarity	NPC199311
0.6136	Remote Similarity	NPC173343
0.6111	Remote Similarity	NPC201148
0.6092	Remote Similarity	NPC283839
0.6076	Remote Similarity	NPC297342
0.6	Remote Similarity	NPC210611
0.5952	Remote Similarity	NPC173150
0.5952	Remote Similarity	NPC476866
0.5882	Remote Similarity	NPC471881
0.5765	Remote Similarity	NPC476869
0.5641	Remote Similarity	NPC479473
0.5641	Remote Similarity	NPC275721
0.5641	Remote Similarity	NPC288416
0.5641	Remote Similarity	NPC479468
0.5641	Remote Similarity	NPC479474
0.5638	Remote Similarity	NPC28651
0.5581	Remote Similarity	NPC226005
0.5581	Remote Similarity	NPC471882
0.557	Remote Similarity	NPC477294
0.557	Remote Similarity	NPC477293
0.5556	Remote Similarity	NPC192763
0.5556	Remote Similarity	NPC34293
0.5529	Remote Similarity	NPC35288
0.5529	Remote Similarity	NPC45224
0.5529	Remote Similarity	NPC476867
0.5484	Remote Similarity	NPC472611
0.5422	Remote Similarity	NPC252114
0.5417	Remote Similarity	NPC232880
0.5393	Remote Similarity	NPC289967
0.5352	Remote Similarity	NPC313193
0.5341	Remote Similarity	NPC205195
0.5316	Remote Similarity	NPC470572
0.5287	Remote Similarity	NPC476864
0.5244	Remote Similarity	NPC291153
0.5233	Remote Similarity	NPC281798
0.5213	Remote Similarity	NPC85192
0.5185	Remote Similarity	NPC229784
0.5169	Remote Similarity	NPC254819
0.5169	Remote Similarity	NPC476868
0.5158	Remote Similarity	NPC215095
0.5114	Remote Similarity	NPC235294
0.5067	Remote Similarity	NPC476872
0.5055	Remote Similarity	NPC476865

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC225307 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	4931
0.1-0.2	4118
0.2-0.3	95
0.3-0.4	5
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