NPASS Compound

Natural Product: NPC89709

Natural Product ID	NPC89709
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	OJNIAAPQTVLMGK-UINLEYECSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	5317157
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 73 77 0 0 0 0 0 0 0 0999 V2000 6.7511 -2.9892 0.1559 C 0 0 0 0 0 0 0 0 0 0 0 0 7.6261 -3.7783 -0.6267 C 0 0 0 0 0 0 0 0 0 0 0 0 7.4712 -3.8838 -1.9882 C 0 0 0 0 0 0 0 0 0 0 0 0 6.4326 -3.1973 -2.5904 C 0 0 0 0 0 0 0 0 0 0 0 0 5.6021 -2.4415 -1.8059 C 0 0 0 0 0 0 0 0 0 0 0 0 5.7284 -2.3108 -0.4221 C 0 0 0 0 0 0 0 0 0 0 0 0 4.7818 -1.4753 0.3095 C 0 0 0 0 0 0 0 0 0 0 0 0 4.7756 -1.2479 1.6533 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8213 -0.4250 2.2739 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8257 -0.2254 3.4983 O 0 0 0 0 0 0 0 0 0 0 0 0 2.8569 0.1752 1.5038 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8848 0.9959 2.0298 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9024 1.6062 1.2395 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9474 1.3485 -0.1104 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9441 0.5096 -0.6345 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9054 -0.0856 0.1511 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8182 -0.8613 -0.3736 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0212 1.9054 -0.9673 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.9998 2.7374 -0.5973 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8480 4.0830 -1.3342 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.1698 4.5734 -1.8780 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.2687 4.4233 -0.8479 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.1972 3.0157 -0.2780 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.5283 2.3567 -0.2186 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4955 1.1570 0.3959 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.7880 0.1237 -0.1518 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.6739 -0.1983 0.8634 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.1326 -1.2277 1.8748 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.4928 -2.5052 1.1386 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.0384 -2.1901 -0.2418 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.0748 -3.2349 -0.5963 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5250 -4.5173 -0.5926 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.6730 -0.9563 -0.2706 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.3844 -3.3237 1.0861 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.1432 -0.7584 2.6825 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.5792 -0.6770 0.1548 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.2687 2.2717 -0.9800 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.0433 5.3772 0.1407 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.4925 3.9564 -3.0834 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.4049 5.0557 -0.4183 O 0 0 0 0 0 0 0 0 0 0 0 0 1.8840 1.2253 3.4106 O 0 0 0 0 0 0 0 0 0 0 0 0 5.7173 -1.8239 2.4653 O 0 0 0 0 0 0 0 0 0 0 0 0 8.3040 -4.6440 -2.7887 O 0 0 0 0 0 0 0 0 0 0 0 0 6.9333 -2.9554 1.2069 H 0 0 0 0 0 0 0 0 0 0 0 0 8.4339 -4.3096 -0.1417 H 0 0 0 0 0 0 0 0 0 0 0 0 6.3034 -3.2762 -3.6710 H 0 0 0 0 0 0 0 0 0 0 0 0 4.7947 -1.9078 -2.2754 H 0 0 0 0 0 0 0 0 0 0 0 0 0.1840 2.2291 1.7271 H 0 0 0 0 0 0 0 0 0 0 0 0 1.9482 0.3322 -1.6870 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0711 2.9653 0.4682 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.1564 3.9814 -2.1947 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.0296 5.6725 -2.0688 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.2496 4.5912 -1.3365 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.7473 3.1340 0.7555 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.9821 2.3178 -1.2509 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.2118 3.0178 0.3946 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.3082 0.3296 -1.1102 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.3693 0.7013 1.4126 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.2541 -1.4518 2.5103 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.2713 -3.0153 1.7422 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.2032 -2.2731 -0.9637 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.5272 -3.0517 -1.5844 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.9093 -3.2453 0.1343 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.1719 -5.0875 -1.1101 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.6040 -4.2744 0.9148 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.1316 0.2311 2.6434 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.8410 -0.7999 0.7818 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.8474 5.6312 0.6337 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.8749 3.2021 -3.2547 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.7388 4.7547 0.4705 H 0 0 0 0 0 0 0 0 0 0 0 0 1.4126 0.5564 4.0209 H 0 0 0 0 0 0 0 0 0 0 0 0 6.3950 -1.3018 3.0082 H 0 0 0 0 0 0 0 0 0 0 0 0 9.3153 -4.6169 -2.6107 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 2 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 9 10 2 0 9 11 1 0 11 12 2 0 12 13 1 0 13 14 2 0 14 15 1 0 15 16 2 0 16 17 1 0 14 18 1 0 18 19 1 0 19 20 1 0 20 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 31 32 1 0 30 33 1 0 29 34 1 0 28 35 1 0 27 36 1 0 23 37 1 0 22 38 1 0 21 39 1 0 20 40 1 0 12 41 1 0 8 42 1 0 3 43 1 0 6 1 1 0 17 7 1 0 37 19 1 0 16 11 1 0 33 26 1 0 1 44 1 0 2 45 1 0 4 46 1 0 5 47 1 0 13 48 1 0 15 49 1 0 19 50 1 1 20 51 1 6 21 52 1 6 22 53 1 6 23 54 1 1 24 55 1 0 24 56 1 0 26 57 1 6 27 58 1 1 28 59 1 1 29 60 1 1 30 61 1 6 31 62 1 0 31 63 1 0 32 64 1 0 34 65 1 0 35 66 1 0 36 67 1 0 38 68 1 0 39 69 1 0 40 70 1 0 41 71 1 0 42 72 1 0 43 73 1 0 M END

Standard InCHIKey	OJNIAAPQTVLMGK-UINLEYECSA-N
Standard InCHI	InChI=1S/C27H30O16/c28-7-14-17(31)20(34)23(37)26(42-14)39-8-15-18(32)21(35)24(38)27(43-15)40-11-5-12(30)16-13(6-11)41-25(22(36)19(16)33)9-1-3-10(29)4-2-9/h1-6,14-15,17-18,20-21,23-24,26-32,34-38H,7-8H2/t14-,15-,17-,18-,20+,21+,23-,24-,26-,27-/m1/s1
SMILES	c1cc(ccc1c1c(c(=O)c2c(cc(cc2o1)O[C@H]1[C@@H]([C@H]([C@@H]([C@@H](CO[C@H]2[C@@H]([C@H]([C@@H]([C@@H](CO)O2)O)O)O)O1)O)O)O)O)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	610.15	Volume:	552.318 ? Van der Waals volume.
Dense:	1.105	LogP:	-0.194 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	0.685 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-3.143 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	7.0	Rigid Bonds:	30.0
TPSA:	269.43 ? Topological Polar Surface Area.	H-Bond Acceptor:	16.0
H-Bond Donor:	10.0	Rings:	5.0
Heavy Atoms:	16.0

MedChem Properties

QED Drug-Likeness Score:	0.133	GASA:	0.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.697	Fsp³:	0.444
MCE-18:	119.436 ? 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:	0.618	Fluc inhibitor:	0.32 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.844 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.628 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.179	Promiscuous compounds:	0.564

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-6.676	MDCK Permeability:	-4.94
Pgp-inhibitor:	0.0	Pgp-substrate:	0.509
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):	0.981
20% Bioavailability (F20%):	0.033	30% Bioavailability (F30%):	0.999
50% Bioavailability (F50%):	0.995

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.112
Plasma Protein Binding (PPB):	82.198%	Volume Distribution (VD):	-0.165
Fu:	18.278% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.389
BSEP inhibitor:	0.001

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:	0.0
CYP3A4-inhibitor:	0.0	CYP3A4-substrate:	0.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.782
HLM stability:	0.022 ? 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):

1.688

Half-life (T1/2):

4.752

ADMET: Toxicity

hERG Blockers:	0.009	hERG Blockers (10um):	0.037
Human Hepatotoxicity (H-HT):	0.492	Drug-induced Liver Injury (DILI):	0.979
AMES Toxicity:	0.946	Rat Oral Acute Toxicity:	0.005
Maximum Recommended Daily Dose:	0.011	Skin Sensitization:	0.997
Carcinogencity:	0.103	Eye Corrosion:	0.0
Eye Irritation:	0.098	Respiratory Toxicity:	0.001
Drug-induced Neurotoxicity:	0.0	Ototoxicity:	0.973
Hematotoxicity:	0.099	Drug-induced Nephrotoxicity:	0.451
Genotoxicity:	0.878	RPMI-8226 Immunitoxicity:	0.11
A549 Cytotoxicity:	0.462	Hek293 Cytotoxicity:	0.507
BCF:	0.369 ? 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:	2.724 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.219 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	3.47 ? 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
NPO2884	Annona squamosa	Species	Annonaceae	Eukaryota	seeds	n.a.	n.a.	PMID[11141125]
NPO2884	Annona squamosa	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12398544]
NPO2884	Annona squamosa	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18419154]
NPO2884	Annona squamosa	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19296389]
NPO2884	Annona squamosa	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21910504]
NPO2884	Annona squamosa	Species	Annonaceae	Eukaryota	seeds	n.a.	n.a.	PMID[22011319]
NPO2884	Annona squamosa	Species	Annonaceae	Eukaryota	n.a.	seed	n.a.	PMID[22011319]
NPO2884	Annona squamosa	Species	Annonaceae	Eukaryota	Barks	n.a.	n.a.	PMID[2348205]
NPO2884	Annona squamosa	Species	Annonaceae	Eukaryota	n.a.	fruit	n.a.	PMID[8786370]
NPO2884	Annona squamosa	Species	Annonaceae	Eukaryota	bark	n.a.	n.a.	PMID[9214729]
NPO21528	Equisetum arvense	Species	Equisetaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO2884	Annona squamosa	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO2884	Annona squamosa	Species	Annonaceae	Eukaryota	Fruit	n.a.	n.a.	Database[FooDB]
NPO2884	Annona squamosa	Species	Annonaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO2884	Annona squamosa	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO21528	Equisetum arvense	Species	Equisetaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO21528	Equisetum arvense	Species	Equisetaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO2884	Annona squamosa	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO21528	Equisetum arvense	Species	Equisetaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO2884	Annona squamosa	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO2884	Annona squamosa	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21528	Equisetum arvense	Species	Equisetaceae	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

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

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 NPC89709 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	22147
0.1-0.2	23341
0.2-0.3	3120
0.3-0.4	767
0.4-0.5	302
0.5-0.6	129
0.6-0.7	29
0.7-0.8	0
0.8-0.85	3
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.8421	Intermediate Similarity	NPC323593
0.8421	Intermediate Similarity	NPC203500
0.8293	Intermediate Similarity	NPC275454
0.7857	Intermediate Similarity	NPC67105
0.75	Intermediate Similarity	NPC277205
0.75	Intermediate Similarity	NPC37919
0.7375	Intermediate Similarity	NPC108831
0.7375	Intermediate Similarity	NPC182634
0.7283	Intermediate Similarity	NPC135358
0.7241	Intermediate Similarity	NPC227508
0.7065	Intermediate Similarity	NPC80068
0.7045	Intermediate Similarity	NPC44931
0.7024	Intermediate Similarity	NPC307938
0.6966	Remote Similarity	NPC479405
0.6889	Remote Similarity	NPC479404
0.6889	Remote Similarity	NPC186816
0.6824	Remote Similarity	NPC285197
0.6782	Remote Similarity	NPC601586
0.6633	Remote Similarity	NPC480796
0.6588	Remote Similarity	NPC84265
0.6566	Remote Similarity	NPC25523
0.6559	Remote Similarity	NPC479403
0.6556	Remote Similarity	NPC187379
0.6552	Remote Similarity	NPC486578
0.6548	Remote Similarity	NPC39360
0.6548	Remote Similarity	NPC29763
0.6548	Remote Similarity	NPC210003
0.6548	Remote Similarity	NPC238376
0.6471	Remote Similarity	NPC297987
0.6458	Remote Similarity	NPC287889
0.6413	Remote Similarity	NPC210073
0.6333	Remote Similarity	NPC477848
0.6237	Remote Similarity	NPC156869
0.6211	Remote Similarity	NPC65711
0.6122	Remote Similarity	NPC101636
0.6111	Remote Similarity	NPC116458
0.6111	Remote Similarity	NPC246943
0.6078	Remote Similarity	NPC480441
0.6064	Remote Similarity	NPC22062
0.6064	Remote Similarity	NPC473634
0.6064	Remote Similarity	NPC303913
0.6064	Remote Similarity	NPC138811
0.5943	Remote Similarity	NPC298666
0.5938	Remote Similarity	NPC64051
0.5909	Remote Similarity	NPC136042
0.5909	Remote Similarity	NPC189142
0.5909	Remote Similarity	NPC77660
0.5843	Remote Similarity	NPC245014
0.5843	Remote Similarity	NPC84362
0.5842	Remote Similarity	NPC244875
0.5824	Remote Similarity	NPC197285
0.5816	Remote Similarity	NPC209296
0.5816	Remote Similarity	NPC35119
0.58	Remote Similarity	NPC298171
0.5789	Remote Similarity	NPC173582
0.5789	Remote Similarity	NPC265885
0.5789	Remote Similarity	NPC181465
0.5789	Remote Similarity	NPC215710
0.5789	Remote Similarity	NPC473438
0.5789	Remote Similarity	NPC253788
0.5778	Remote Similarity	NPC117260
0.5773	Remote Similarity	NPC488073
0.5773	Remote Similarity	NPC64425
0.5758	Remote Similarity	NPC270675
0.5758	Remote Similarity	NPC195685
0.5729	Remote Similarity	NPC183672
0.5728	Remote Similarity	NPC189564
0.5714	Remote Similarity	NPC143799
0.5684	Remote Similarity	NPC471079
0.5682	Remote Similarity	NPC331652
0.567	Remote Similarity	NPC169733
0.5657	Remote Similarity	NPC32641
0.5657	Remote Similarity	NPC256188
0.5657	Remote Similarity	NPC473623
0.5652	Remote Similarity	NPC601144
0.5618	Remote Similarity	NPC289667
0.5618	Remote Similarity	NPC261866
0.5618	Remote Similarity	NPC249281
0.5618	Remote Similarity	NPC476405
0.5604	Remote Similarity	NPC21100
0.5604	Remote Similarity	NPC27942
0.56	Remote Similarity	NPC142142
0.56	Remote Similarity	NPC488089
0.5591	Remote Similarity	NPC136761
0.5591	Remote Similarity	NPC311830
0.5591	Remote Similarity	NPC605784
0.5588	Remote Similarity	NPC472994
0.5567	Remote Similarity	NPC473512
0.5567	Remote Similarity	NPC65003
0.5567	Remote Similarity	NPC129827
0.5567	Remote Similarity	NPC65563
0.5567	Remote Similarity	NPC470949
0.5567	Remote Similarity	NPC102028
0.5556	Remote Similarity	NPC197896
0.5556	Remote Similarity	NPC95090
0.5556	Remote Similarity	NPC313163
0.5556	Remote Similarity	NPC27408
0.5556	Remote Similarity	NPC609879
0.5532	Remote Similarity	NPC276377
0.551	Remote Similarity	NPC473571
0.551	Remote Similarity	NPC110941
0.55	Remote Similarity	NPC57751
0.5495	Remote Similarity	NPC46420
0.5484	Remote Similarity	NPC243930
0.5481	Remote Similarity	NPC121703
0.5481	Remote Similarity	NPC599948
0.5426	Remote Similarity	NPC607707
0.5421	Remote Similarity	NPC311850
0.5417	Remote Similarity	NPC8856
0.5408	Remote Similarity	NPC233994
0.5408	Remote Similarity	NPC203259
0.5408	Remote Similarity	NPC33054
0.5408	Remote Similarity	NPC176740
0.5408	Remote Similarity	NPC471725
0.5408	Remote Similarity	NPC134532
0.5408	Remote Similarity	NPC150164
0.5408	Remote Similarity	NPC602582
0.5385	Remote Similarity	NPC282987
0.5385	Remote Similarity	NPC14187
0.5377	Remote Similarity	NPC292019
0.5377	Remote Similarity	NPC202908
0.5377	Remote Similarity	NPC472993
0.537	Remote Similarity	NPC488083
0.5347	Remote Similarity	NPC139060
0.5347	Remote Similarity	NPC229409
0.534	Remote Similarity	NPC292929
0.5333	Remote Similarity	NPC203145
0.5319	Remote Similarity	NPC22832
0.5306	Remote Similarity	NPC67326
0.5306	Remote Similarity	NPC47923
0.53	Remote Similarity	NPC240306
0.5288	Remote Similarity	NPC602448
0.5278	Remote Similarity	NPC277532
0.5275	Remote Similarity	NPC77672
0.5275	Remote Similarity	NPC133671
0.5275	Remote Similarity	NPC135391
0.5275	Remote Similarity	NPC78263
0.5275	Remote Similarity	NPC250069
0.5273	Remote Similarity	NPC68592
0.5248	Remote Similarity	NPC211532
0.5248	Remote Similarity	NPC488364
0.5225	Remote Similarity	NPC198199
0.5217	Remote Similarity	NPC93337
0.5217	Remote Similarity	NPC146792
0.5213	Remote Similarity	NPC80140
0.52	Remote Similarity	NPC122809
0.5185	Remote Similarity	NPC164704
0.5172	Remote Similarity	NPC191154
0.5161	Remote Similarity	NPC24043
0.5161	Remote Similarity	NPC105025
0.5161	Remote Similarity	NPC610763
0.5155	Remote Similarity	NPC172807
0.5149	Remote Similarity	NPC46202
0.5109	Remote Similarity	NPC19709
0.5109	Remote Similarity	NPC83283
0.5102	Remote Similarity	NPC251417
0.5098	Remote Similarity	NPC470443
0.5096	Remote Similarity	NPC476472
0.5096	Remote Similarity	NPC294815
0.5096	Remote Similarity	NPC16194
0.5096	Remote Similarity	NPC188815
0.5088	Remote Similarity	NPC120952
0.5052	Remote Similarity	NPC61791
0.5052	Remote Similarity	NPC190003
0.505	Remote Similarity	NPC204693
0.505	Remote Similarity	NPC115674
0.505	Remote Similarity	NPC131745
0.5049	Remote Similarity	NPC483707
0.5049	Remote Similarity	NPC72016
0.5048	Remote Similarity	NPC470449
0.5047	Remote Similarity	NPC11468

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC89709 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	5574
0.1-0.2	3497
0.2-0.3	64
0.3-0.4	9
0.4-0.5	2
0.5-0.6	3
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
0.602	Remote Similarity	NPD7251	Phase 2
0.5816	Remote Similarity	NPD7054	Phase 4
0.5631	Remote Similarity	NPD7808	Phase 3
0.5408	Remote Similarity	NPD6797	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