NPASS Compound

Natural Product: NPC173837

Natural Product ID	NPC173837
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	3'-O-Methylquercetin3-O-Alpha-L-Rhamnopyranosyl(1->6)-2''-O-Acetyl-Beta-D-Glucopyranoside
IUPAC Name	[(2S,3R,4S,5S,6R)-2-[5,7-dihydroxy-2-(4-hydroxy-3-methoxyphenyl)-4-oxochromen-3-yl]oxy-4,5-dihydroxy-6-[[(2R,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxymethyl]oxan-3-yl] acetate
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL499959
PubChem CID	10032376
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 81 85 0 0 0 0 0 0 0 0999 V2000 -7.7049 -0.9640 1.5882 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9513 -1.8997 2.3284 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.5819 -2.0007 2.0222 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.9835 -1.2461 1.0720 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6213 -1.3160 0.7308 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9003 -2.2293 1.4439 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4878 -3.0299 2.4416 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.8286 -2.9122 2.7266 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.4439 -3.6959 3.7151 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.1618 -0.4924 -0.3565 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0728 0.0716 -1.1729 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.7839 0.8188 -2.1806 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.7651 1.3659 -2.9795 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4614 2.1611 -4.0540 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.4534 2.7249 -4.8760 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.1520 2.4569 -4.3956 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1581 1.9223 -3.6125 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4700 1.1258 -2.5358 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5004 0.5806 -1.7385 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2665 0.7839 -1.9534 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.8729 -0.2359 -0.6366 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8239 -0.7365 0.1375 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.2894 0.2074 1.0860 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8706 0.7023 0.4555 O 0 0 0 0 0 0 0 0 0 0 0 0 1.9153 0.9493 1.3240 C 0 0 2 0 0 0 0 0 0 0 0 0 2.9352 1.8524 0.7492 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5182 1.5449 -0.3929 O 0 0 0 0 0 0 0 0 0 0 0 0 4.3289 0.4890 -0.6144 C 0 0 2 0 0 0 0 0 0 0 0 0 5.6611 0.9505 -0.8764 O 0 0 0 0 0 0 0 0 0 0 0 0 6.1163 0.5797 -2.1277 C 0 0 1 0 0 0 0 0 0 0 0 0 7.5311 1.1781 -2.2275 C 0 0 0 0 0 0 0 0 0 0 0 0 6.2146 -0.9341 -2.1622 C 0 0 1 0 0 0 0 0 0 0 0 0 4.8057 -1.4696 -2.1234 C 0 0 2 0 0 0 0 0 0 0 0 0 3.8516 -0.3534 -1.7571 C 0 0 1 0 0 0 0 0 0 0 0 0 2.6409 -0.9349 -1.4395 O 0 0 0 0 0 0 0 0 0 0 0 0 4.6613 -2.4768 -1.1802 O 0 0 0 0 0 0 0 0 0 0 0 0 6.9058 -1.3807 -3.2890 O 0 0 0 0 0 0 0 0 0 0 0 0 2.3583 -0.3214 1.9499 C 0 0 2 0 0 0 0 0 0 0 0 0 1.2109 -0.8934 2.7820 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.1214 -0.2536 2.4656 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.2325 0.8381 3.4175 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.1014 0.8145 4.4753 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8342 -0.2110 4.6153 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.2417 1.9207 5.4739 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0584 -2.2650 2.5352 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4371 -0.1590 2.8216 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8427 2.2016 -3.9270 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.3993 0.0846 1.7398 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.8022 -1.1117 1.7441 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.5101 -1.1839 0.5008 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.6063 -0.5262 0.5300 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.8725 -2.3658 1.2343 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.9132 -3.7468 3.0023 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.1995 -3.2530 4.2521 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.8139 1.1683 -2.7640 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.0461 3.4283 -4.4445 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.9349 3.0895 -5.2520 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.9460 1.1402 1.1244 H 0 0 0 0 0 0 0 0 0 0 0 0 1.4709 1.6102 2.1958 H 0 0 0 0 0 0 0 0 0 0 0 0 2.4866 2.9055 0.6325 H 0 0 0 0 0 0 0 0 0 0 0 0 3.7336 2.0922 1.5594 H 0 0 0 0 0 0 0 0 0 0 0 0 4.4058 -0.1424 0.2939 H 0 0 0 0 0 0 0 0 0 0 0 0 5.4949 0.9455 -2.9731 H 0 0 0 0 0 0 0 0 0 0 0 0 7.4847 2.2843 -2.2295 H 0 0 0 0 0 0 0 0 0 0 0 0 8.1302 0.8826 -1.3416 H 0 0 0 0 0 0 0 0 0 0 0 0 8.0477 0.8744 -3.1424 H 0 0 0 0 0 0 0 0 0 0 0 0 6.7259 -1.2368 -1.2376 H 0 0 0 0 0 0 0 0 0 0 0 0 4.4835 -1.8796 -3.1111 H 0 0 0 0 0 0 0 0 0 0 0 0 3.6368 0.2937 -2.6639 H 0 0 0 0 0 0 0 0 0 0 0 0 2.5045 -1.6809 -2.0923 H 0 0 0 0 0 0 0 0 0 0 0 0 5.2630 -2.2456 -0.4314 H 0 0 0 0 0 0 0 0 0 0 0 0 7.3772 -2.2144 -3.0283 H 0 0 0 0 0 0 0 0 0 0 0 0 2.5915 -1.1001 1.2220 H 0 0 0 0 0 0 0 0 0 0 0 0 1.4158 -0.7866 3.8643 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.8861 -0.9960 2.8282 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.4513 1.8349 6.2386 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0945 2.8818 4.9364 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.2645 1.9304 5.9065 H 0 0 0 0 0 0 0 0 0 0 0 0 1.8821 -2.5526 2.0578 H 0 0 0 0 0 0 0 0 0 0 0 0 3.2679 0.5640 3.4842 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.5748 3.1832 -4.1075 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 5 10 1 0 10 11 1 0 11 12 1 0 12 13 2 0 13 14 1 0 14 15 1 0 14 16 2 0 16 17 1 0 17 18 2 0 18 19 1 0 19 20 2 0 19 21 1 0 21 22 1 0 22 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 1 0 29 30 1 0 30 31 1 0 30 32 1 0 32 33 1 0 33 34 1 0 34 35 1 0 33 36 1 0 32 37 1 0 25 38 1 0 38 39 1 0 39 40 1 0 40 41 1 0 41 42 1 0 42 43 2 0 42 44 1 0 39 45 1 0 38 46 1 0 17 47 1 0 8 3 1 0 21 10 2 0 40 23 1 0 18 12 1 0 34 28 1 0 1 48 1 0 1 49 1 0 1 50 1 0 4 51 1 0 6 52 1 0 7 53 1 0 9 54 1 0 13 55 1 0 15 56 1 0 16 57 1 0 23 58 1 1 25 59 1 1 26 60 1 0 26 61 1 0 28 62 1 1 30 63 1 6 31 64 1 0 31 65 1 0 31 66 1 0 32 67 1 1 33 68 1 6 34 69 1 6 35 70 1 0 36 71 1 0 37 72 1 0 38 73 1 6 39 74 1 1 40 75 1 1 44 76 1 0 44 77 1 0 44 78 1 0 45 79 1 0 46 80 1 0 47 81 1 0 M END

Standard InCHIKey	HVTVSIKZCOWXGV-HWXBTJPQSA-N
Standard InCHI	InChI=1S/C30H34O17/c1-10-20(35)23(38)25(40)29(43-10)42-9-18-21(36)24(39)28(44-11(2)31)30(46-18)47-27-22(37)19-15(34)7-13(32)8-17(19)45-26(27)12-4-5-14(33)16(6-12)41-3/h4-8,10,18,20-21,23-25,28-30,32-36,38-40H,9H2,1-3H3/t10-,18+,20-,21+,23+,24-,25+,28+,29+,30-/m0/s1
SMILES	COc1cc(ccc1O)c1oc2cc(O)cc(c2c(=O)c1O[C@@H]1O[C@H](CO[C@@H]2O[C@@H](C)[C@@H]([C@H]([C@H]2O)O)O)[C@H]([C@@H]([C@H]1OC(=O)C)O)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	666.18	Volume:	610.359 ? Van der Waals volume.
Dense:	1.091	LogP:	0.741 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	1.154 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-3.339 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	9.0	Rigid Bonds:	31.0
TPSA:	264.5 ? Topological Polar Surface Area.	H-Bond Acceptor:	17.0
H-Bond Donor:	8.0	Rings:	5.0
Heavy Atoms:	17.0

MedChem Properties

QED Drug-Likeness Score:	0.137	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.853	Fsp³:	0.467
MCE-18:	124.364 ? 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:	0.608	Fluc inhibitor:	0.248 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.768 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.586 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.073	Promiscuous compounds:	0.401

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-6.227	MDCK Permeability:	-5.376
Pgp-inhibitor:	0.007	Pgp-substrate:	0.905
PAMPA:	0.986 ? 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):	0.299
20% Bioavailability (F20%):	0.162	30% Bioavailability (F30%):	0.991
50% Bioavailability (F50%):	0.999

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.148
Plasma Protein Binding (PPB):	82.451%	Volume Distribution (VD):	-0.131
Fu:	15.005% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.98
BSEP inhibitor:	0.203

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:	0.106
CYP3A4-inhibitor:	0.0	CYP3A4-substrate:	0.034
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.999
HLM stability:	0.779 ? 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):

0.936

Half-life (T1/2):

3.409

ADMET: Toxicity

hERG Blockers:	0.014	hERG Blockers (10um):	0.127
Human Hepatotoxicity (H-HT):	0.431	Drug-induced Liver Injury (DILI):	0.876
AMES Toxicity:	0.865	Rat Oral Acute Toxicity:	0.01
Maximum Recommended Daily Dose:	0.03	Skin Sensitization:	0.996
Carcinogencity:	0.065	Eye Corrosion:	0.0
Eye Irritation:	0.366	Respiratory Toxicity:	0.003
Drug-induced Neurotoxicity:	0.001	Ototoxicity:	0.885
Hematotoxicity:	0.061	Drug-induced Nephrotoxicity:	0.303
Genotoxicity:	0.905	RPMI-8226 Immunitoxicity:	0.167
A549 Cytotoxicity:	0.426	Hek293 Cytotoxicity:	0.552
BCF:	0.448 ? 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:	3.114 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.542 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	3.72 ? 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
NPO28679	Prunus mume	Species	Rosaceae	Eukaryota	flowers	n.a.	n.a.	PMID[12193020]
NPO28679	Prunus mume	Species	Rosaceae	Eukaryota	fruits	n.a.	n.a.	PMID[24485782]
NPO28679	Prunus mume	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO28679	Prunus mume	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO28679	Prunus mume	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO28679	Prunus mume	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO28679	Prunus mume	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO28679	Prunus mume	Species	Rosaceae	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	1

Activity Type	# Activity
Individual protein	1

Molecular-level activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT68	Individual protein	Aldose reductase	Rattus norvegicus	IC50	=	9800.0	nM	PMID[12193020]

In vitro activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference

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 NPC173837 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	15509
0.1-0.2	30485
0.2-0.3	2998
0.3-0.4	460
0.4-0.5	201
0.5-0.6	132
0.6-0.7	39
0.7-0.8	0
0.8-0.85	4
0.85-0.9	0
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.9121	High Similarity	NPC89052
0.8478	Intermediate Similarity	NPC89127
0.8085	Intermediate Similarity	NPC476472
0.8085	Intermediate Similarity	NPC294815
0.8085	Intermediate Similarity	NPC16194
0.7766	Intermediate Similarity	NPC12013
0.7766	Intermediate Similarity	NPC11432
0.7766	Intermediate Similarity	NPC477613
0.7684	Intermediate Similarity	NPC122467
0.7547	Intermediate Similarity	NPC192539
0.7526	Intermediate Similarity	NPC220173
0.7449	Intermediate Similarity	NPC221342
0.7449	Intermediate Similarity	NPC476470
0.7374	Intermediate Similarity	NPC602448
0.7264	Intermediate Similarity	NPC162394
0.7143	Intermediate Similarity	NPC473327
0.7113	Intermediate Similarity	NPC153755
0.7019	Intermediate Similarity	NPC303694
0.6989	Remote Similarity	NPC223747
0.6903	Remote Similarity	NPC473554
0.6804	Remote Similarity	NPC173582
0.6804	Remote Similarity	NPC265885
0.6804	Remote Similarity	NPC181465
0.6804	Remote Similarity	NPC215710
0.6804	Remote Similarity	NPC473438
0.6804	Remote Similarity	NPC253788
0.6735	Remote Similarity	NPC203259
0.6735	Remote Similarity	NPC33054
0.6735	Remote Similarity	NPC176740
0.6735	Remote Similarity	NPC471725
0.6735	Remote Similarity	NPC134532
0.6735	Remote Similarity	NPC602582
0.6733	Remote Similarity	NPC142142
0.6697	Remote Similarity	NPC480445
0.6667	Remote Similarity	NPC216496
0.6602	Remote Similarity	NPC292929
0.6583	Remote Similarity	NPC487501
0.6577	Remote Similarity	NPC480444
0.6562	Remote Similarity	NPC476215
0.65	Remote Similarity	NPC487500
0.6495	Remote Similarity	NPC95866
0.6379	Remote Similarity	NPC487499
0.6303	Remote Similarity	NPC487502
0.63	Remote Similarity	NPC39834
0.63	Remote Similarity	NPC163242
0.63	Remote Similarity	NPC272068
0.6296	Remote Similarity	NPC219043
0.6238	Remote Similarity	NPC155877
0.6224	Remote Similarity	NPC203050
0.6224	Remote Similarity	NPC225434
0.6186	Remote Similarity	NPC224530
0.6116	Remote Similarity	NPC249560
0.6091	Remote Similarity	NPC217520
0.6082	Remote Similarity	NPC219904
0.604	Remote Similarity	NPC609888
0.6019	Remote Similarity	NPC473571
0.6019	Remote Similarity	NPC110941
0.5982	Remote Similarity	NPC139571
0.5963	Remote Similarity	NPC203145
0.5962	Remote Similarity	NPC126784
0.5962	Remote Similarity	NPC241423
0.5948	Remote Similarity	NPC209550
0.5946	Remote Similarity	NPC25523
0.5926	Remote Similarity	NPC218161
0.5922	Remote Similarity	NPC156869
0.5917	Remote Similarity	NPC275977
0.5882	Remote Similarity	NPC471079
0.5877	Remote Similarity	NPC488734
0.5877	Remote Similarity	NPC488735
0.5877	Remote Similarity	NPC488739
0.5877	Remote Similarity	NPC488732
0.5877	Remote Similarity	NPC488738
0.5842	Remote Similarity	NPC116864
0.5842	Remote Similarity	NPC244776
0.5825	Remote Similarity	NPC67326
0.582	Remote Similarity	NPC72554
0.5812	Remote Similarity	NPC241781
0.5804	Remote Similarity	NPC480441
0.5798	Remote Similarity	NPC25946
0.5785	Remote Similarity	NPC231787
0.5776	Remote Similarity	NPC488740
0.5776	Remote Similarity	NPC488736
0.5776	Remote Similarity	NPC488733
0.5769	Remote Similarity	NPC304741
0.575	Remote Similarity	NPC21359
0.575	Remote Similarity	NPC460984
0.5743	Remote Similarity	NPC170052
0.5743	Remote Similarity	NPC135846
0.5741	Remote Similarity	NPC470447
0.5729	Remote Similarity	NPC111929
0.5729	Remote Similarity	NPC320283
0.5729	Remote Similarity	NPC41121
0.5728	Remote Similarity	NPC187379
0.5714	Remote Similarity	NPC48984
0.5714	Remote Similarity	NPC255157
0.5714	Remote Similarity	NPC259896
0.57	Remote Similarity	NPC259957
0.5691	Remote Similarity	NPC30011
0.5688	Remote Similarity	NPC470445
0.5686	Remote Similarity	NPC254855
0.5686	Remote Similarity	NPC94610
0.5678	Remote Similarity	NPC488737
0.567	Remote Similarity	NPC127546
0.567	Remote Similarity	NPC57625
0.567	Remote Similarity	NPC173637
0.567	Remote Similarity	NPC317489
0.567	Remote Similarity	NPC223424
0.567	Remote Similarity	NPC600591
0.5641	Remote Similarity	NPC156785
0.5641	Remote Similarity	NPC474522
0.5635	Remote Similarity	NPC97817
0.563	Remote Similarity	NPC480443
0.5625	Remote Similarity	NPC473072
0.5625	Remote Similarity	NPC189564
0.5619	Remote Similarity	NPC65563
0.5619	Remote Similarity	NPC470949
0.5612	Remote Similarity	NPC265530
0.5607	Remote Similarity	NPC470443
0.5596	Remote Similarity	NPC471669
0.5583	Remote Similarity	NPC480442
0.5575	Remote Similarity	NPC292019
0.5575	Remote Similarity	NPC202908
0.5566	Remote Similarity	NPC470444
0.5566	Remote Similarity	NPC186816
0.5524	Remote Similarity	NPC470405
0.5514	Remote Similarity	NPC240306
0.5506	Remote Similarity	NPC279989
0.5505	Remote Similarity	NPC97119
0.5505	Remote Similarity	NPC603079
0.5472	Remote Similarity	NPC605592
0.5455	Remote Similarity	NPC76831
0.5446	Remote Similarity	NPC48093
0.5439	Remote Similarity	NPC477895
0.5424	Remote Similarity	NPC470713
0.5421	Remote Similarity	NPC35167
0.5405	Remote Similarity	NPC470449
0.5392	Remote Similarity	NPC120099
0.5392	Remote Similarity	NPC609478
0.5357	Remote Similarity	NPC470446
0.5321	Remote Similarity	NPC483414
0.5299	Remote Similarity	NPC470718
0.5294	Remote Similarity	NPC159579
0.5294	Remote Similarity	NPC60735
0.5294	Remote Similarity	NPC175107
0.5294	Remote Similarity	NPC26230
0.5263	Remote Similarity	NPC11468
0.5253	Remote Similarity	NPC135599
0.5253	Remote Similarity	NPC73855
0.5253	Remote Similarity	NPC113968
0.5253	Remote Similarity	NPC328940
0.5253	Remote Similarity	NPC277174
0.5253	Remote Similarity	NPC606877
0.5246	Remote Similarity	NPC175429
0.5243	Remote Similarity	NPC484158
0.5229	Remote Similarity	NPC488073
0.5229	Remote Similarity	NPC488074
0.52	Remote Similarity	NPC104677
0.5196	Remote Similarity	NPC472459
0.5196	Remote Similarity	NPC325555
0.5196	Remote Similarity	NPC226304
0.5192	Remote Similarity	NPC209023
0.5179	Remote Similarity	NPC85751
0.5179	Remote Similarity	NPC19240
0.5167	Remote Similarity	NPC198199
0.5164	Remote Similarity	NPC120952
0.5149	Remote Similarity	NPC33083
0.5146	Remote Similarity	NPC129217
0.514	Remote Similarity	NPC258044
0.514	Remote Similarity	NPC217387
0.5138	Remote Similarity	NPC129264
0.5128	Remote Similarity	NPC470712
0.5096	Remote Similarity	NPC101026
0.5096	Remote Similarity	NPC488077
0.5091	Remote Similarity	NPC64425
0.5088	Remote Similarity	NPC223426
0.5086	Remote Similarity	NPC470451
0.505	Remote Similarity	NPC77672
0.505	Remote Similarity	NPC133671
0.505	Remote Similarity	NPC135391
0.505	Remote Similarity	NPC78263
0.505	Remote Similarity	NPC250069
0.5044	Remote Similarity	NPC195257
0.5044	Remote Similarity	NPC473073
0.5043	Remote Similarity	NPC470455
0.5043	Remote Similarity	NPC214621
0.5043	Remote Similarity	NPC34267
0.5043	Remote Similarity	NPC483765
0.5043	Remote Similarity	NPC81042
0.5041	Remote Similarity	NPC298666

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC173837 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	5139
0.1-0.2	3962
0.2-0.3	40
0.3-0.4	4
0.4-0.5	1
0.5-0.6	2
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	Drug ID	Developmental Stage
0.6735	Remote Similarity	NPD6797	Phase 2
0.5263	Remote Similarity	NPD7808	Phase 3
0.5179	Remote Similarity	NPD7251	Phase 2

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