NPASS Compound

Natural Product: NPC80188

Natural Product ID	NPC80188
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	LADIAAQZFHPJSX-PFKOEMKTSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	5318496
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000334] Flavonoids [CHEMONTID:0001111] Flavonoid glycosides [CHEMONTID:0001583] Flavonoid O-glycosides [CHEMONTID:0003533] Flavonoid-7-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 59 62 0 0 0 0 0 0 0 0999 V2000 -1.8168 3.2791 1.8386 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6504 2.6283 0.8206 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9404 3.0966 -0.2946 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.1796 1.3731 1.0962 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.9796 0.6466 0.2306 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.3404 0.3098 0.7226 C 0 0 2 0 0 0 0 0 0 0 0 0 -6.0554 -0.5082 -0.3194 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.2302 -1.6692 -0.8209 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.9223 -2.3702 -1.9794 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.9104 -1.5647 -3.1276 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.9292 -1.3705 -1.0858 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.2744 -0.6523 -0.1064 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.9594 -0.3477 -0.4089 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8136 -0.6979 0.2618 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8220 -1.4527 1.4065 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3658 -1.7963 2.0721 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5872 -1.3821 1.5915 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7470 -1.7177 2.2416 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7503 -2.4092 3.2918 O 0 0 0 0 0 0 0 0 0 0 0 0 3.9322 -1.2531 1.6802 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9011 -0.5084 0.5460 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1385 -0.0070 -0.0650 C 0 0 0 0 0 0 0 0 0 0 0 0 6.3789 -0.2594 0.4689 C 0 0 0 0 0 0 0 0 0 0 0 0 7.5069 0.2584 -0.1803 C 0 0 0 0 0 0 0 0 0 0 0 0 7.4063 1.0089 -1.3317 C 0 0 0 0 0 0 0 0 0 0 0 0 6.1581 1.2565 -1.8593 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0449 0.7557 -1.2341 C 0 0 0 0 0 0 0 0 0 0 0 0 8.5719 1.4877 -1.9170 O 0 0 0 0 0 0 0 0 0 0 0 0 8.4935 2.2551 -3.0917 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7590 -0.2337 -0.0095 O 0 0 0 0 0 0 0 0 0 0 0 0 1.5946 -0.6244 0.4422 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4393 -0.2824 -0.2170 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3343 -2.5563 3.2220 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.2609 -0.9916 0.2364 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.1324 1.4576 0.9348 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.1852 2.5544 2.4183 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0794 3.9602 1.3257 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.3840 3.9269 2.5331 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.1030 1.2645 -0.7024 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.2941 -0.3125 1.6435 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.3529 0.0927 -1.2033 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.2305 -2.4128 0.0189 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.3989 -3.3053 -2.2641 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.9511 -2.6697 -1.7013 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.8358 -1.5639 -3.4788 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.3226 -1.2622 0.8119 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.7446 -1.8064 1.8317 H 0 0 0 0 0 0 0 0 0 0 0 0 4.8287 -1.5302 2.2096 H 0 0 0 0 0 0 0 0 0 0 0 0 6.4916 -0.8393 1.3630 H 0 0 0 0 0 0 0 0 0 0 0 0 8.4736 0.0351 0.2761 H 0 0 0 0 0 0 0 0 0 0 0 0 6.0848 1.8512 -2.7708 H 0 0 0 0 0 0 0 0 0 0 0 0 4.0598 0.9534 -1.6539 H 0 0 0 0 0 0 0 0 0 0 0 0 7.8304 1.7807 -3.8311 H 0 0 0 0 0 0 0 0 0 0 0 0 9.4753 2.3860 -3.5725 H 0 0 0 0 0 0 0 0 0 0 0 0 8.0222 3.2371 -2.8160 H 0 0 0 0 0 0 0 0 0 0 0 0 0.4234 0.3092 -1.1168 H 0 0 0 0 0 0 0 0 0 0 0 0 0.2103 -3.5517 3.1778 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.8573 -0.2743 0.4975 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.0535 2.0191 0.1276 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 2 0 2 4 1 0 4 5 1 0 5 6 1 0 6 7 1 0 7 8 1 0 8 9 1 0 9 10 1 0 8 11 1 0 11 12 1 0 12 13 1 0 13 14 1 0 14 15 2 0 15 16 1 0 16 17 2 0 17 18 1 0 18 19 2 0 18 20 1 0 20 21 2 0 21 22 1 0 22 23 2 0 23 24 1 0 24 25 2 0 25 26 1 0 26 27 2 0 25 28 1 0 28 29 1 0 21 30 1 0 30 31 1 0 31 32 2 0 16 33 1 0 7 34 1 0 6 35 1 0 12 5 1 0 32 14 1 0 31 17 1 0 27 22 1 0 1 36 1 0 1 37 1 0 1 38 1 0 5 39 1 6 6 40 1 1 7 41 1 6 8 42 1 1 9 43 1 0 9 44 1 0 10 45 1 0 12 46 1 1 15 47 1 0 20 48 1 0 23 49 1 0 24 50 1 0 26 51 1 0 27 52 1 0 29 53 1 0 29 54 1 0 29 55 1 0 32 56 1 0 33 57 1 0 34 58 1 0 35 59 1 0 M END

Standard InCHIKey	LADIAAQZFHPJSX-PFKOEMKTSA-N
Standard InCHI	InChI=1S/C24H24O11/c1-11(26)32-23-22(30)21(29)19(10-25)35-24(23)33-14-7-15(27)20-16(28)9-17(34-18(20)8-14)12-3-5-13(31-2)6-4-12/h3-9,19,21-25,27,29-30H,10H2,1-2H3/t19-,21-,22+,23-,24-/m1/s1
SMILES	CC(=O)O[C@@H]1[C@H]([C@@H]([C@@H](CO)O[C@H]1Oc1cc(c2c(=O)cc(c3ccc(cc3)OC)oc2c1)O)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	488.13	Volume:	462.399 ? Van der Waals volume.
Dense:	1.056	LogP:	1.482 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	1.88 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-3.555 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	7.0	Rigid Bonds:	25.0
TPSA:	165.12 ? Topological Polar Surface Area.	H-Bond Acceptor:	11.0
H-Bond Donor:	4.0	Rings:	4.0
Heavy Atoms:	11.0

MedChem Properties

QED Drug-Likeness Score:	0.365	GASA:	0.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	3.851	Fsp³:	0.333
MCE-18:	86.125 ? MCE-18 stands for medicinal chemistry evolution.MCE-18≥45 is considered a suitable value.	Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Rejected	GSK Rule:	Accepted
Golden Triangle Rule:	Rejected	BMS Rule:	0
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.67	Fluc inhibitor:	0.547 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.949 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.877 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.112	Promiscuous compounds:	0.375

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.892	MDCK Permeability:	-5.021
Pgp-inhibitor:	0.019	Pgp-substrate:	0.519
PAMPA:	0.931 ? 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):	0.97
20% Bioavailability (F20%):	0.718	30% Bioavailability (F30%):	0.999
50% Bioavailability (F50%):	0.998

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.001	MRP1:	0.456
Plasma Protein Binding (PPB):	83.851%	Volume Distribution (VD):	-0.11
Fu:	17.201% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.609
BSEP inhibitor:	0.028

ADMET: Metabolism

CYP1A2-inhibitor:	0.002	CYP1A2-substrate:	0.001
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.001
CYP2C9-inhibitor:	0.032	CYP2C9-substrate:	0.236
CYP2D6-inhibitor:	0.091	CYP2D6-substrate:	0.196
CYP3A4-inhibitor:	0.0	CYP3A4-substrate:	0.042
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	1.0
HLM stability:	0.318 ? 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):

2.702

Half-life (T1/2):

1.855

ADMET: Toxicity

hERG Blockers:	0.033	hERG Blockers (10um):	0.083
Human Hepatotoxicity (H-HT):	0.729	Drug-induced Liver Injury (DILI):	0.997
AMES Toxicity:	0.951	Rat Oral Acute Toxicity:	0.043
Maximum Recommended Daily Dose:	0.051	Skin Sensitization:	0.994
Carcinogencity:	0.658	Eye Corrosion:	0.0
Eye Irritation:	0.451	Respiratory Toxicity:	0.035
Drug-induced Neurotoxicity:	0.008	Ototoxicity:	0.736
Hematotoxicity:	0.361	Drug-induced Nephrotoxicity:	0.734
Genotoxicity:	0.954	RPMI-8226 Immunitoxicity:	0.119
A549 Cytotoxicity:	0.336	Hek293 Cytotoxicity:	0.344
BCF:	0.455 ? 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:	3.244 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.658 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	3.895 ? 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
NPO26351	Agastache rugosa	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11908994]
NPO26351	Agastache rugosa	Species	Lamiaceae	Eukaryota	n.a.	root	n.a.	PMID[1823989]
NPO26351	Agastache rugosa	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[31747281]
NPO26351	Agastache rugosa	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[38791403]
NPO26351	Agastache rugosa	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[8594148]
NPO12265	Aquilaria agallochum	Species	Thymelaeaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO3392	Agastache rugosus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO26351	Agastache rugosa	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO3392	Agastache rugosus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO3392	Agastache rugosus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO12265	Aquilaria agallochum	Species	Thymelaeaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO26351	Agastache rugosa	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO26351	Agastache rugosa	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO12265	Aquilaria agallochum	Species	Thymelaeaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO26351	Agastache rugosa	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12265	Aquilaria agallochum	Species	Thymelaeaceae	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
Cell line	1

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
NPT113	Cell line	RAW264.7	Mus musculus	IC50	=	4700.0	nM	PMID[31747281]

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 NPC80188 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	12192
0.1-0.2	33552
0.2-0.3	3100
0.3-0.4	690
0.4-0.5	218
0.5-0.6	66
0.6-0.7	29
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
0.7403	Intermediate Similarity	NPC95090
0.7403	Intermediate Similarity	NPC27408
0.7375	Intermediate Similarity	NPC220169
0.7241	Intermediate Similarity	NPC479766
0.686	Remote Similarity	NPC65003
0.6842	Remote Similarity	NPC488083
0.6782	Remote Similarity	NPC122809
0.6737	Remote Similarity	NPC311850
0.6706	Remote Similarity	NPC8856
0.6667	Remote Similarity	NPC181712
0.6593	Remote Similarity	NPC195257
0.6593	Remote Similarity	NPC475382
0.6591	Remote Similarity	NPC115674
0.6531	Remote Similarity	NPC68592
0.6429	Remote Similarity	NPC22832
0.6429	Remote Similarity	NPC243930
0.6316	Remote Similarity	NPC11468
0.6311	Remote Similarity	NPC262222
0.6286	Remote Similarity	NPC29353
0.622	Remote Similarity	NPC39360
0.622	Remote Similarity	NPC29763
0.622	Remote Similarity	NPC210003
0.6163	Remote Similarity	NPC607707
0.6162	Remote Similarity	NPC488087
0.6154	Remote Similarity	NPC64425
0.6136	Remote Similarity	NPC606546
0.6129	Remote Similarity	NPC488089
0.6111	Remote Similarity	NPC22062
0.6111	Remote Similarity	NPC473634
0.6111	Remote Similarity	NPC138811
0.61	Remote Similarity	NPC488088
0.6087	Remote Similarity	NPC477628
0.604	Remote Similarity	NPC488086
0.598	Remote Similarity	NPC198199
0.5977	Remote Similarity	NPC311830
0.596	Remote Similarity	NPC473644
0.5952	Remote Similarity	NPC189142
0.5952	Remote Similarity	NPC77660
0.5938	Remote Similarity	NPC253685
0.5895	Remote Similarity	NPC479765
0.5882	Remote Similarity	NPC186807
0.5851	Remote Similarity	NPC473623
0.5833	Remote Similarity	NPC58053
0.5833	Remote Similarity	NPC261866
0.5825	Remote Similarity	NPC298666
0.5814	Remote Similarity	NPC27942
0.581	Remote Similarity	NPC120952
0.5806	Remote Similarity	NPC46202
0.5794	Remote Similarity	NPC199172
0.5714	Remote Similarity	NPC331652
0.5682	Remote Similarity	NPC601144
0.5682	Remote Similarity	NPC608742
0.5647	Remote Similarity	NPC143851
0.5638	Remote Similarity	NPC472992
0.5596	Remote Similarity	NPC35924
0.5506	Remote Similarity	NPC224530
0.5465	Remote Similarity	NPC19709
0.5405	Remote Similarity	NPC127447
0.5385	Remote Similarity	NPC190003
0.5361	Remote Similarity	NPC210961
0.5361	Remote Similarity	NPC209296
0.5357	Remote Similarity	NPC248739
0.5349	Remote Similarity	NPC14606
0.5349	Remote Similarity	NPC473043
0.534	Remote Similarity	NPC470715
0.5333	Remote Similarity	NPC234133
0.5326	Remote Similarity	NPC211594
0.5325	Remote Similarity	NPC195202
0.5325	Remote Similarity	NPC223579
0.5312	Remote Similarity	NPC240306
0.5306	Remote Similarity	NPC472991
0.5287	Remote Similarity	NPC289667
0.5287	Remote Similarity	NPC121649
0.5283	Remote Similarity	NPC295625
0.5233	Remote Similarity	NPC158027
0.5227	Remote Similarity	NPC18699
0.5208	Remote Similarity	NPC257566
0.52	Remote Similarity	NPC101636
0.52	Remote Similarity	NPC298171
0.5192	Remote Similarity	NPC164704
0.5169	Remote Similarity	NPC602537
0.5165	Remote Similarity	NPC486578
0.5158	Remote Similarity	NPC44931
0.5138	Remote Similarity	NPC470720
0.5132	Remote Similarity	NPC231772
0.5132	Remote Similarity	NPC145379
0.5109	Remote Similarity	NPC88023
0.5109	Remote Similarity	NPC309025
0.5065	Remote Similarity	NPC108406
0.5056	Remote Similarity	NPC93337
0.5055	Remote Similarity	NPC285197
0.5055	Remote Similarity	NPC609451
0.5051	Remote Similarity	NPC124155
0.5051	Remote Similarity	NPC32641
0.5051	Remote Similarity	NPC256188
0.5051	Remote Similarity	NPC139060
0.5051	Remote Similarity	NPC35119
0.5046	Remote Similarity	NPC470719
0.5046	Remote Similarity	NPC470717

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC80188 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	4228
0.1-0.2	4829
0.2-0.3	80
0.3-0.4	11
0.4-0.5	1
0.5-0.6	1
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
0.5361	Remote Similarity	NPD7054	Phase 4

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