NPASS Compound

Natural Product: NPC473682

Natural Product ID	NPC473682
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	Eupalitin 3-O-Beta-D-Glucopyranosyl-(1->2)-Beta-D-Glucopyranoside
IUPAC Name	3-[(2S,3R,4S,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]oxy-5-hydroxy-2-(4-hydroxyphenyl)-6,7-dimethoxychromen-4-one
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL449077
PubChem CID	10794364
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000334] Flavonoids [CHEMONTID:0001111] Flavonoid glycosides [CHEMONTID:0001583] Flavonoid O-glycosides [CHEMONTID:0003531] Flavonoid-3-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 80 84 0 0 0 0 0 0 0 0999 V2000 1.6269 -0.8330 -5.5959 O 0 0 0 0 0 0 0 0 0 0 0 0 1.3401 0.1434 -4.6278 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9538 -0.3331 -3.3323 C 0 0 1 0 0 0 0 0 0 0 0 0 1.7098 0.6122 -2.3742 O 0 0 0 0 0 0 0 0 0 0 0 0 0.9782 0.2081 -1.2936 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.3587 0.0305 -1.7042 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.4966 0.2380 -0.9990 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0972 1.4569 -0.9028 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2140 1.5867 -0.1731 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.7916 0.6160 0.4699 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2544 -0.6474 0.4217 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0911 -0.8109 -0.3318 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6463 -1.9715 -0.3509 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.8526 -1.6746 1.0983 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2931 -2.9442 1.0342 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.9780 -1.5090 1.8361 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.5584 -0.2213 1.9076 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.9337 0.8229 1.2068 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.6424 0.0223 2.6000 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.6661 0.5821 3.1756 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.6443 -2.4771 2.5499 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.6900 -3.2861 2.1264 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6543 2.7035 -1.5217 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7748 2.7409 -2.5492 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3158 3.9583 -3.0840 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7423 5.1558 -2.5880 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6465 5.1459 -1.5360 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0775 3.9374 -1.0324 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2616 6.3613 -3.1450 O 0 0 0 0 0 0 0 0 0 0 0 0 1.4978 -0.9900 -0.5978 C 0 0 1 0 0 0 0 0 0 0 0 0 1.6832 -2.1037 -1.5755 C 0 0 2 0 0 0 0 0 0 0 0 0 1.4798 -1.7083 -3.0072 C 0 0 2 0 0 0 0 0 0 0 0 0 2.0905 -2.6658 -3.8115 O 0 0 0 0 0 0 0 0 0 0 0 0 0.9624 -3.2389 -1.2421 O 0 0 0 0 0 0 0 0 0 0 0 0 2.6243 -0.7627 0.1790 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5618 -0.9155 1.4950 C 0 0 2 0 0 0 0 0 0 0 0 0 2.9678 0.1778 2.2049 O 0 0 0 0 0 0 0 0 0 0 0 0 4.2367 0.6136 2.1543 C 0 0 2 0 0 0 0 0 0 0 0 0 4.5474 1.2940 0.8266 C 0 0 0 0 0 0 0 0 0 0 0 0 5.8881 1.7520 0.8454 O 0 0 0 0 0 0 0 0 0 0 0 0 5.2760 -0.4387 2.3796 C 0 0 1 0 0 0 0 0 0 0 0 0 4.9265 -1.6950 1.6689 C 0 0 1 0 0 0 0 0 0 0 0 0 3.4847 -2.0884 1.8777 C 0 0 1 0 0 0 0 0 0 0 0 0 3.3061 -2.4532 3.1982 O 0 0 0 0 0 0 0 0 0 0 0 0 5.3260 -1.7357 0.3442 O 0 0 0 0 0 0 0 0 0 0 0 0 6.5447 0.0245 1.9690 O 0 0 0 0 0 0 0 0 0 0 0 0 1.1769 -0.5055 -6.4363 H 0 0 0 0 0 0 0 0 0 0 0 0 0.2190 0.1945 -4.5667 H 0 0 0 0 0 0 0 0 0 0 0 0 1.6907 1.1378 -4.9310 H 0 0 0 0 0 0 0 0 0 0 0 0 3.0505 -0.3684 -3.4995 H 0 0 0 0 0 0 0 0 0 0 0 0 1.0112 1.0302 -0.5112 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.9259 -3.7525 1.0814 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.3318 1.8304 1.2213 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.6081 1.7066 3.3661 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.6497 0.4842 2.6277 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.9123 0.1431 4.1952 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.2552 -4.2220 1.7182 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.2920 -3.5854 3.0237 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.3939 -2.8099 1.4058 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.4090 1.8699 -3.0528 H 0 0 0 0 0 0 0 0 0 0 0 0 0.3895 3.9829 -3.9078 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.9747 6.0946 -1.1577 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.7881 3.8989 -0.2010 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.3342 7.2372 -2.6558 H 0 0 0 0 0 0 0 0 0 0 0 0 0.7495 -1.2980 0.1523 H 0 0 0 0 0 0 0 0 0 0 0 0 2.7730 -2.4265 -1.4372 H 0 0 0 0 0 0 0 0 0 0 0 0 0.3953 -1.7681 -3.2249 H 0 0 0 0 0 0 0 0 0 0 0 0 3.0644 -2.6584 -3.7734 H 0 0 0 0 0 0 0 0 0 0 0 0 1.4829 -4.0714 -1.3440 H 0 0 0 0 0 0 0 0 0 0 0 0 1.5765 -1.2327 1.9110 H 0 0 0 0 0 0 0 0 0 0 0 0 4.3568 1.4020 2.9654 H 0 0 0 0 0 0 0 0 0 0 0 0 4.4775 0.5407 0.0398 H 0 0 0 0 0 0 0 0 0 0 0 0 3.8867 2.1517 0.7454 H 0 0 0 0 0 0 0 0 0 0 0 0 5.8563 2.7061 1.1045 H 0 0 0 0 0 0 0 0 0 0 0 0 5.3549 -0.6286 3.4890 H 0 0 0 0 0 0 0 0 0 0 0 0 5.5222 -2.5161 2.1733 H 0 0 0 0 0 0 0 0 0 0 0 0 3.2845 -2.9825 1.2585 H 0 0 0 0 0 0 0 0 0 0 0 0 3.7201 -1.7632 3.7694 H 0 0 0 0 0 0 0 0 0 0 0 0 6.2284 -2.1148 0.2383 H 0 0 0 0 0 0 0 0 0 0 0 0 7.2766 -0.3870 2.5014 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 1 0 7 8 2 0 8 9 1 0 9 10 1 0 10 11 2 0 11 12 1 0 12 13 2 0 11 14 1 0 14 15 1 0 14 16 2 0 16 17 1 0 17 18 2 0 17 19 1 0 19 20 1 0 16 21 1 0 21 22 1 0 8 23 1 0 23 24 2 0 24 25 1 0 25 26 2 0 26 27 1 0 27 28 2 0 26 29 1 0 5 30 1 0 30 31 1 0 31 32 1 0 32 33 1 0 31 34 1 0 30 35 1 0 35 36 1 0 36 37 1 0 37 38 1 0 38 39 1 0 39 40 1 0 38 41 1 0 41 42 1 0 42 43 1 0 43 44 1 0 42 45 1 0 41 46 1 0 32 3 1 0 43 36 1 0 12 7 1 0 28 23 1 0 18 10 1 0 1 47 1 0 2 48 1 0 2 49 1 0 3 50 1 6 5 51 1 1 15 52 1 0 18 53 1 0 20 54 1 0 20 55 1 0 20 56 1 0 22 57 1 0 22 58 1 0 22 59 1 0 24 60 1 0 25 61 1 0 27 62 1 0 28 63 1 0 29 64 1 0 30 65 1 1 31 66 1 6 32 67 1 6 33 68 1 0 34 69 1 0 36 70 1 6 38 71 1 1 39 72 1 0 39 73 1 0 40 74 1 0 41 75 1 1 42 76 1 1 43 77 1 6 44 78 1 0 45 79 1 0 46 80 1 0 M END

Standard InCHIKey	RUQZEYSGSQAXQA-LZIGPTKVSA-N
Standard InCHI	InChI=1S/C29H34O17/c1-40-13-7-12-16(19(35)25(13)41-2)20(36)26(24(42-12)10-3-5-11(32)6-4-10)45-29-27(22(38)18(34)15(9-31)44-29)46-28-23(39)21(37)17(33)14(8-30)43-28/h3-7,14-15,17-18,21-23,27-35,37-39H,8-9H2,1-2H3/t14-,15-,17+,18-,21+,22+,23-,27-,28+,29+/m1/s1
SMILES	OC[C@H]1O[C@@H](Oc2c(oc3c(c2=O)c(O)c(c(c3)OC)OC)c2ccc(cc2)O)[C@@H]([C@H]([C@@H]1O)O)O[C@@H]1O[C@H](CO)[C@@H]([C@@H]([C@H]1O)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	654.18	Volume:	595.7 ? Van der Waals volume.
Dense:	1.098	LogP:	-0.001 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	0.812 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-2.643 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	9.0	Rigid Bonds:	30.0
TPSA:	267.66 ? Topological Polar Surface Area.	H-Bond Acceptor:	17.0
H-Bond Donor:	9.0	Rings:	5.0
Heavy Atoms:	17.0

MedChem Properties

QED Drug-Likeness Score:	0.119	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.741	Fsp³:	0.483
MCE-18:	121.279 ? 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:	1
Chelating Alert:	1	PAINS Alert:	0
Colloidal aggregators:	0.593	Fluc inhibitor:	0.261 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.671 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.6 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.113	Promiscuous compounds:	0.455

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-6.41	MDCK Permeability:	-5.327
Pgp-inhibitor:	0.0	Pgp-substrate:	0.58
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):	0.994
20% Bioavailability (F20%):	0.62	30% Bioavailability (F30%):	0.999
50% Bioavailability (F50%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.271
Plasma Protein Binding (PPB):	80.9%	Volume Distribution (VD):	-0.07
Fu:	17.094% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.998
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.139
BSEP inhibitor:	0.0

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:	0.002
CYP3A4-inhibitor:	0.0	CYP3A4-substrate:	0.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.829
HLM stability:	0.019 ? 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):

1.656

Half-life (T1/2):

2.942

ADMET: Toxicity

hERG Blockers:	0.008	hERG Blockers (10um):	0.035
Human Hepatotoxicity (H-HT):	0.736	Drug-induced Liver Injury (DILI):	0.932
AMES Toxicity:	0.946	Rat Oral Acute Toxicity:	0.015
Maximum Recommended Daily Dose:	0.009	Skin Sensitization:	1.0
Carcinogencity:	0.274	Eye Corrosion:	0.0
Eye Irritation:	0.178	Respiratory Toxicity:	0.007
Drug-induced Neurotoxicity:	0.017	Ototoxicity:	0.977
Hematotoxicity:	0.603	Drug-induced Nephrotoxicity:	0.695
Genotoxicity:	0.719	RPMI-8226 Immunitoxicity:	0.141
A549 Cytotoxicity:	0.893	Hek293 Cytotoxicity:	0.727
BCF:	0.311 ? 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:	2.825 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.607 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	3.565 ? 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
NPO32923	boerhaavia repens	Species	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[8946741]

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	3

Activity Type	# Activity
Tissue	3

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
NPT6346	Tissue	Bone	Mus musculus	Inhibition	=	38.0	%	PMID[23398362]
NPT6346	Tissue	Bone	Mus musculus	Inhibition	=	60.3	%	PMID[23398362]
NPT6346	Tissue	Bone	Mus musculus	Inhibition	=	29.1	%	PMID[23398362]

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 NPC473682 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	24018
0.1-0.2	21485
0.2-0.3	3389
0.3-0.4	557
0.4-0.5	275
0.5-0.6	96
0.6-0.7	21
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
0.7821	Intermediate Similarity	NPC24043
0.7647	Intermediate Similarity	NPC470444
0.7561	Intermediate Similarity	NPC170052
0.7561	Intermediate Similarity	NPC135846
0.7558	Intermediate Similarity	NPC240306
0.7191	Intermediate Similarity	NPC35119
0.7033	Intermediate Similarity	NPC473071
0.7021	Intermediate Similarity	NPC473072
0.7011	Intermediate Similarity	NPC163242
0.7011	Intermediate Similarity	NPC272068
0.7	Intermediate Similarity	NPC32641
0.7	Intermediate Similarity	NPC256188
0.686	Remote Similarity	NPC254855
0.686	Remote Similarity	NPC94610
0.6588	Remote Similarity	NPC488071
0.6556	Remote Similarity	NPC304741
0.6444	Remote Similarity	NPC470405
0.6413	Remote Similarity	NPC64425
0.6374	Remote Similarity	NPC155877
0.6364	Remote Similarity	NPC488072
0.6353	Remote Similarity	NPC488080
0.6353	Remote Similarity	NPC169977
0.6316	Remote Similarity	NPC220173
0.6211	Remote Similarity	NPC142142
0.62	Remote Similarity	NPC25523
0.6186	Remote Similarity	NPC602448
0.618	Remote Similarity	NPC476215
0.6136	Remote Similarity	NPC21666
0.6082	Remote Similarity	NPC292929
0.6081	Remote Similarity	NPC101830
0.6047	Remote Similarity	NPC93337
0.6047	Remote Similarity	NPC297987
0.6	Remote Similarity	NPC488075
0.5979	Remote Similarity	NPC76831
0.5977	Remote Similarity	NPC27640
0.5977	Remote Similarity	NPC105025
0.5977	Remote Similarity	NPC603655
0.5957	Remote Similarity	NPC255157
0.5957	Remote Similarity	NPC259896
0.5955	Remote Similarity	NPC224530
0.5851	Remote Similarity	NPC65003
0.5833	Remote Similarity	NPC480471
0.5833	Remote Similarity	NPC488076
0.5784	Remote Similarity	NPC48984
0.5747	Remote Similarity	NPC77672
0.5747	Remote Similarity	NPC133671
0.5747	Remote Similarity	NPC135391
0.5747	Remote Similarity	NPC78263
0.5747	Remote Similarity	NPC250069
0.5728	Remote Similarity	NPC164704
0.5727	Remote Similarity	NPC25946
0.5714	Remote Similarity	NPC116458
0.5714	Remote Similarity	NPC246943
0.5701	Remote Similarity	NPC470717
0.5699	Remote Similarity	NPC8856
0.567	Remote Similarity	NPC12013
0.567	Remote Similarity	NPC483414
0.567	Remote Similarity	NPC11432
0.567	Remote Similarity	NPC477613
0.5638	Remote Similarity	NPC139320
0.5631	Remote Similarity	NPC219043
0.5591	Remote Similarity	NPC95866
0.5577	Remote Similarity	NPC480441
0.5577	Remote Similarity	NPC470715
0.5568	Remote Similarity	NPC289667
0.5568	Remote Similarity	NPC58053
0.5556	Remote Similarity	NPC42773
0.5556	Remote Similarity	NPC45522
0.5543	Remote Similarity	NPC136761
0.5505	Remote Similarity	NPC470720
0.549	Remote Similarity	NPC14187
0.5455	Remote Similarity	NPC209550
0.5444	Remote Similarity	NPC46420
0.5444	Remote Similarity	NPC84362
0.5444	Remote Similarity	NPC45638
0.5435	Remote Similarity	NPC101026
0.5435	Remote Similarity	NPC488077
0.5408	Remote Similarity	NPC61904
0.5385	Remote Similarity	NPC472459
0.5385	Remote Similarity	NPC117260
0.5385	Remote Similarity	NPC201292
0.537	Remote Similarity	NPC295625
0.5347	Remote Similarity	NPC195257
0.5333	Remote Similarity	NPC8573
0.5333	Remote Similarity	NPC64305
0.5333	Remote Similarity	NPC136042
0.5326	Remote Similarity	NPC168584
0.5326	Remote Similarity	NPC609451
0.5315	Remote Similarity	NPC138990
0.5306	Remote Similarity	NPC115674
0.5294	Remote Similarity	NPC221342
0.5294	Remote Similarity	NPC476470
0.5283	Remote Similarity	NPC470712
0.5275	Remote Similarity	NPC186807
0.5269	Remote Similarity	NPC605067
0.5268	Remote Similarity	NPC175429
0.5263	Remote Similarity	NPC21359
0.5263	Remote Similarity	NPC460984
0.5256	Remote Similarity	NPC110070
0.5253	Remote Similarity	NPC488073
0.5227	Remote Similarity	NPC288084
0.5222	Remote Similarity	NPC249281
0.5217	Remote Similarity	NPC205076
0.5213	Remote Similarity	NPC602805
0.5196	Remote Similarity	NPC483412
0.519	Remote Similarity	NPC18772
0.5182	Remote Similarity	NPC470713
0.5165	Remote Similarity	NPC145038
0.5165	Remote Similarity	NPC56077
0.5165	Remote Similarity	NPC281131
0.5165	Remote Similarity	NPC253662
0.5165	Remote Similarity	NPC179950
0.5165	Remote Similarity	NPC88789
0.5165	Remote Similarity	NPC491374
0.5158	Remote Similarity	NPC203050
0.5158	Remote Similarity	NPC225434
0.5155	Remote Similarity	NPC29958
0.5152	Remote Similarity	NPC473571
0.5152	Remote Similarity	NPC110941
0.5149	Remote Similarity	NPC122467
0.5149	Remote Similarity	NPC482026
0.5143	Remote Similarity	NPC89052
0.5106	Remote Similarity	NPC120099
0.5102	Remote Similarity	NPC471748
0.5054	Remote Similarity	NPC216496
0.5054	Remote Similarity	NPC599850
0.5053	Remote Similarity	NPC605784
0.505	Remote Similarity	NPC483415
0.5045	Remote Similarity	NPC480445

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC473682 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	5957
0.1-0.2	3108
0.2-0.3	76
0.3-0.4	4
0.4-0.5	5
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