NPASS Compound

Natural Product: NPC110248

Natural Product ID	NPC110248
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	GFEDXTCTEYKKLQ-UJKBSQBPSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	5320846
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000334] Flavonoids [CHEMONTID:0001615] Flavones

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 61 64 0 0 0 0 0 0 0 0999 V2000 -2.3756 -2.1004 -0.8815 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1065 -3.4443 -0.5958 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7092 -4.1257 0.4378 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6236 -3.4820 1.2454 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8859 -2.1681 0.9662 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2803 -1.4479 -0.0873 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6267 -0.0456 -0.2318 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9456 0.8242 -1.0039 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3788 2.1680 -1.0663 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7336 2.9616 -1.7911 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.4781 2.5436 -0.3366 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.8828 3.8784 -0.4169 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.9837 4.2589 0.3135 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.6433 3.3365 1.0869 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.2305 2.0265 1.1538 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1251 1.6037 0.4325 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.6960 0.3787 0.4619 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.7504 3.7383 1.8161 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.1943 4.7984 -1.2117 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.8452 0.4722 -1.7311 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.5414 0.7947 -1.3408 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3990 1.4285 -0.2866 O 0 0 0 0 0 0 0 0 0 0 0 0 0.5479 0.3491 -2.2225 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8842 0.7339 -1.7237 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3487 1.8777 -1.9291 O 0 0 0 0 0 0 0 0 0 0 0 0 2.6212 -0.2005 -1.0186 O 0 0 0 0 0 0 0 0 0 0 0 0 3.9100 0.0733 -0.5015 C 0 0 1 0 0 0 0 0 0 0 0 0 3.8052 -0.0589 1.0158 C 0 0 1 0 0 0 0 0 0 0 0 0 5.1759 -0.0967 1.6359 C 0 0 2 0 0 0 0 0 0 0 0 0 6.2216 0.1904 0.6010 C 0 0 1 0 0 0 0 0 0 0 0 0 6.0917 -0.6674 -0.6145 C 0 0 1 0 0 0 0 0 0 0 0 0 6.6966 -2.0446 -0.3785 C 0 0 0 0 0 0 0 0 0 0 0 0 8.0198 -1.8984 0.0453 O 0 0 0 0 0 0 0 0 0 0 0 0 4.7840 -0.8566 -1.0325 O 0 0 0 0 0 0 0 0 0 0 0 0 6.2617 1.5353 0.2371 O 0 0 0 0 0 0 0 0 0 0 0 0 5.4618 -1.3319 2.2225 O 0 0 0 0 0 0 0 0 0 0 0 0 3.1345 1.0564 1.4871 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.2294 -4.1727 2.2862 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.3802 -5.4714 0.6522 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.8891 -1.6383 -1.7185 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.3762 -3.9222 -1.2571 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.6086 -1.6691 1.6104 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.3265 5.2724 0.2798 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.7365 1.2872 1.7560 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.6135 3.9731 1.3405 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.2737 4.7039 -2.2267 H 0 0 0 0 0 0 0 0 0 0 0 0 0.4594 -0.7647 -2.3676 H 0 0 0 0 0 0 0 0 0 0 0 0 0.3839 0.7833 -3.2459 H 0 0 0 0 0 0 0 0 0 0 0 0 4.1500 1.1264 -0.7863 H 0 0 0 0 0 0 0 0 0 0 0 0 3.2233 -0.9779 1.2481 H 0 0 0 0 0 0 0 0 0 0 0 0 5.2711 0.6897 2.4329 H 0 0 0 0 0 0 0 0 0 0 0 0 7.2213 -0.0373 1.0727 H 0 0 0 0 0 0 0 0 0 0 0 0 6.6637 -0.2259 -1.4636 H 0 0 0 0 0 0 0 0 0 0 0 0 6.6406 -2.6367 -1.3205 H 0 0 0 0 0 0 0 0 0 0 0 0 6.0707 -2.5947 0.3547 H 0 0 0 0 0 0 0 0 0 0 0 0 8.5885 -2.0925 -0.7621 H 0 0 0 0 0 0 0 0 0 0 0 0 7.1939 1.7834 -0.0370 H 0 0 0 0 0 0 0 0 0 0 0 0 4.6433 -1.8391 2.4541 H 0 0 0 0 0 0 0 0 0 0 0 0 3.6597 1.8646 1.2149 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.0911 -4.6980 2.1134 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.1736 -5.8031 1.5760 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 12 19 1 0 8 20 1 0 20 21 1 0 21 22 2 0 21 23 1 0 23 24 1 0 24 25 2 0 24 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 32 33 1 0 31 34 1 0 30 35 1 0 29 36 1 0 28 37 1 0 4 38 1 0 3 39 1 0 6 1 1 0 17 7 1 0 34 27 1 0 16 11 1 0 1 40 1 0 2 41 1 0 5 42 1 0 13 43 1 0 15 44 1 0 18 45 1 0 19 46 1 0 23 47 1 0 23 48 1 0 27 49 1 1 28 50 1 6 29 51 1 1 30 52 1 1 31 53 1 6 32 54 1 0 32 55 1 0 33 56 1 0 35 57 1 0 36 58 1 0 37 59 1 0 38 60 1 0 39 61 1 0 M END

Standard InCHIKey	GFEDXTCTEYKKLQ-UJKBSQBPSA-N
Standard InCHI	InChI=1S/C24H22O15/c25-7-14-18(32)20(34)21(35)24(37-14)39-16(31)6-15(30)38-23-19(33)17-12(29)4-9(26)5-13(17)36-22(23)8-1-2-10(27)11(28)3-8/h1-5,14,18,20-21,24-29,32,34-35H,6-7H2/t14-,18-,20+,21-,24+/m1/s1
SMILES	c1cc(c(cc1c1c(c(=O)c2c(cc(cc2o1)O)O)OC(=O)CC(=O)O[C@H]1[C@@H]([C@H]([C@@H]([C@@H](CO)O1)O)O)O)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	550.1	Volume:	494.923 ? Van der Waals volume.
Dense:	1.111	LogP:	0.825 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	1.169 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-3.364 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	8.0	Rigid Bonds:	26.0
TPSA:	253.88 ? 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:	0.103	GASA:	0.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.26	Fsp³:	0.292
MCE-18:	96.355 ? 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:	1
Colloidal aggregators:	0.703	Fluc inhibitor:	0.281 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.968 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.624 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.101	Promiscuous compounds:	0.597

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-6.274	MDCK Permeability:	-5.059
Pgp-inhibitor:	0.0	Pgp-substrate:	0.001
PAMPA:	0.991 ? 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):	0.267
20% Bioavailability (F20%):	0.068	30% Bioavailability (F30%):	0.991
50% Bioavailability (F50%):	0.999

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.001	MRP1:	0.055
Plasma Protein Binding (PPB):	77.71%	Volume Distribution (VD):	-0.191
Fu:	19.967% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.013
BSEP inhibitor:	0.014

ADMET: Metabolism

CYP1A2-inhibitor:	0.006	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.005
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.69
CYP3A4-inhibitor:	0.0	CYP3A4-substrate:	0.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	1.0
HLM stability:	0.863 ? 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):

2.826

Half-life (T1/2):

3.35

ADMET: Toxicity

hERG Blockers:	0.003	hERG Blockers (10um):	0.075
Human Hepatotoxicity (H-HT):	0.661	Drug-induced Liver Injury (DILI):	0.918
AMES Toxicity:	0.909	Rat Oral Acute Toxicity:	0.08
Maximum Recommended Daily Dose:	0.189	Skin Sensitization:	1.0
Carcinogencity:	0.28	Eye Corrosion:	0.0
Eye Irritation:	0.387	Respiratory Toxicity:	0.022
Drug-induced Neurotoxicity:	0.001	Ototoxicity:	0.916
Hematotoxicity:	0.102	Drug-induced Nephrotoxicity:	0.324
Genotoxicity:	0.995	RPMI-8226 Immunitoxicity:	0.046
A549 Cytotoxicity:	0.813	Hek293 Cytotoxicity:	0.388
BCF:	0.464 ? 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:	3.226 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.532 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.021 ? 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
NPO26589	Artemisia annua L.	Strain	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[ 21030913]
NPO26589	Artemisia annua L.	Strain	Asteraceae	Eukaryota	n.a.	stem	n.a.	DOI[10.1007/s11418-006-0112-9]
NPO26589	Artemisia annua L.	Strain	Asteraceae	Eukaryota	n.a.	flower	n.a.	DOI[10.1007/s11418-006-0112-9]
NPO26589	Artemisia annua L.	Strain	Asteraceae	Eukaryota	n.a.	leaf	n.a.	DOI[10.1007/s11418-006-0112-9]
NPO26589	Artemisia annua L.	Strain	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[6387056]
NPO1854	Cardiospermum hirsutum	Species	Sapindaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO4787	Capuronianthus mahafalensis	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO10756	Callitris drummondii	Species	Cupressaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO26589	Artemisia annua L.	Strain	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO8002	Solanum olgae	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO23847	Lysimachia christinae	Species	Primulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO28334	Pyrola decorata	Species	Ericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO26589	Artemisia annua L.	Strain	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO23847	Lysimachia christinae	Species	Primulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO28334	Pyrola decorata	Species	Ericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO27772	Flos inulae	Species	Lycaenidae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO1854	Cardiospermum hirsutum	Species	Sapindaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO1854	Cardiospermum hirsutum	Species	Sapindaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO23847	Lysimachia christinae	Species	Primulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO28334	Pyrola decorata	Species	Ericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO27772	Flos inulae	Species	Lycaenidae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO26589	Artemisia annua L.	Strain	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO23847	Lysimachia christinae	Species	Primulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO28334	Pyrola decorata	Species	Ericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO26589	Artemisia annua L.	Strain	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO26589	Artemisia annua L.	Strain	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO23847	Lysimachia christinae	Species	Primulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO23847	Lysimachia christinae	Species	Primulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26589	Artemisia annua L.	Strain	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1854	Cardiospermum hirsutum	Species	Sapindaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10756	Callitris drummondii	Species	Cupressaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4787	Capuronianthus mahafalensis	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8002	Solanum olgae	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28334	Pyrola decorata	Species	Ericaceae	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 NPC110248 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	13426
0.1-0.2	31393
0.2-0.3	4042
0.3-0.4	559
0.4-0.5	228
0.5-0.6	146
0.6-0.7	45
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
0.7294	Intermediate Similarity	NPC254855
0.7294	Intermediate Similarity	NPC94610
0.7073	Intermediate Similarity	NPC145038
0.7073	Intermediate Similarity	NPC56077
0.7073	Intermediate Similarity	NPC281131
0.7073	Intermediate Similarity	NPC253662
0.7073	Intermediate Similarity	NPC179950
0.7073	Intermediate Similarity	NPC88789
0.7073	Intermediate Similarity	NPC491374
0.6977	Remote Similarity	NPC170052
0.6977	Remote Similarity	NPC135846
0.6932	Remote Similarity	NPC29958
0.6854	Remote Similarity	NPC470405
0.6854	Remote Similarity	NPC471748
0.6778	Remote Similarity	NPC155877
0.6778	Remote Similarity	NPC156869
0.6747	Remote Similarity	NPC77672
0.6747	Remote Similarity	NPC133671
0.6747	Remote Similarity	NPC135391
0.6747	Remote Similarity	NPC78263
0.6747	Remote Similarity	NPC250069
0.6556	Remote Similarity	NPC139320
0.6522	Remote Similarity	NPC255157
0.6522	Remote Similarity	NPC259896
0.6506	Remote Similarity	NPC67037
0.6506	Remote Similarity	NPC255615
0.6484	Remote Similarity	NPC163242
0.6484	Remote Similarity	NPC272068
0.6353	Remote Similarity	NPC19388
0.6353	Remote Similarity	NPC240431
0.6353	Remote Similarity	NPC55786
0.6333	Remote Similarity	NPC95866
0.6279	Remote Similarity	NPC64305
0.625	Remote Similarity	NPC60735
0.625	Remote Similarity	NPC175107
0.625	Remote Similarity	NPC26230
0.6237	Remote Similarity	NPC304741
0.6237	Remote Similarity	NPC605592
0.6224	Remote Similarity	NPC602448
0.619	Remote Similarity	NPC288084
0.618	Remote Similarity	NPC120099
0.618	Remote Similarity	NPC224530
0.618	Remote Similarity	NPC609478
0.6163	Remote Similarity	NPC127546
0.6163	Remote Similarity	NPC57625
0.6163	Remote Similarity	NPC173637
0.6163	Remote Similarity	NPC317489
0.6163	Remote Similarity	NPC223424
0.6163	Remote Similarity	NPC600591
0.6139	Remote Similarity	NPC292019
0.6139	Remote Similarity	NPC202908
0.6136	Remote Similarity	NPC472459
0.6122	Remote Similarity	NPC292929
0.6044	Remote Similarity	NPC476215
0.5979	Remote Similarity	NPC122467
0.5978	Remote Similarity	NPC116864
0.5978	Remote Similarity	NPC244776
0.5957	Remote Similarity	NPC67326
0.5941	Remote Similarity	NPC203145
0.5938	Remote Similarity	NPC253521
0.5938	Remote Similarity	NPC113836
0.5895	Remote Similarity	NPC203259
0.5895	Remote Similarity	NPC33054
0.5895	Remote Similarity	NPC176740
0.5895	Remote Similarity	NPC471725
0.5895	Remote Similarity	NPC134532
0.5895	Remote Similarity	NPC602582
0.5882	Remote Similarity	NPC189564
0.587	Remote Similarity	NPC203050
0.587	Remote Similarity	NPC225434
0.5862	Remote Similarity	NPC111929
0.5862	Remote Similarity	NPC320283
0.5862	Remote Similarity	NPC41121
0.5859	Remote Similarity	NPC471669
0.5859	Remote Similarity	NPC89127
0.5833	Remote Similarity	NPC480444
0.5826	Remote Similarity	NPC249560
0.5814	Remote Similarity	NPC276222
0.5814	Remote Similarity	NPC274618
0.5814	Remote Similarity	NPC34531
0.5814	Remote Similarity	NPC118284
0.5814	Remote Similarity	NPC608147
0.5773	Remote Similarity	NPC61904
0.5714	Remote Similarity	NPC12013
0.5714	Remote Similarity	NPC11432
0.5714	Remote Similarity	NPC477613
0.57	Remote Similarity	NPC76831
0.57	Remote Similarity	NPC220173
0.5684	Remote Similarity	NPC471079
0.566	Remote Similarity	NPC470718
0.5625	Remote Similarity	NPC173582
0.5625	Remote Similarity	NPC265885
0.5625	Remote Similarity	NPC181465
0.5625	Remote Similarity	NPC215710
0.5625	Remote Similarity	NPC473438
0.5625	Remote Similarity	NPC253788
0.5619	Remote Similarity	NPC470712
0.5604	Remote Similarity	NPC42773
0.5604	Remote Similarity	NPC216496
0.5604	Remote Similarity	NPC45522
0.5604	Remote Similarity	NPC325555
0.5604	Remote Similarity	NPC226304
0.5596	Remote Similarity	NPC162394
0.5588	Remote Similarity	NPC223426
0.5575	Remote Similarity	NPC21359
0.5575	Remote Similarity	NPC460984
0.5556	Remote Similarity	NPC136042
0.5543	Remote Similarity	NPC159579
0.5524	Remote Similarity	NPC219043
0.5517	Remote Similarity	NPC54802
0.5517	Remote Similarity	NPC197304
0.5513	Remote Similarity	NPC286342
0.5506	Remote Similarity	NPC135599
0.5506	Remote Similarity	NPC73855
0.5506	Remote Similarity	NPC113968
0.5506	Remote Similarity	NPC328940
0.5506	Remote Similarity	NPC277174
0.5506	Remote Similarity	NPC606877
0.5505	Remote Similarity	NPC480445
0.55	Remote Similarity	NPC37668
0.5495	Remote Similarity	NPC488737
0.5495	Remote Similarity	NPC84362
0.5484	Remote Similarity	NPC259957
0.5472	Remote Similarity	NPC303694
0.5455	Remote Similarity	NPC488073
0.5455	Remote Similarity	NPC488740
0.5455	Remote Similarity	NPC488736
0.5455	Remote Similarity	NPC488733
0.5435	Remote Similarity	NPC599850
0.5426	Remote Similarity	NPC136761
0.5385	Remote Similarity	NPC297987
0.5377	Remote Similarity	NPC48984
0.5376	Remote Similarity	NPC219904
0.5354	Remote Similarity	NPC35167
0.5354	Remote Similarity	NPC144097
0.5351	Remote Similarity	NPC25946
0.5347	Remote Similarity	NPC270448
0.534	Remote Similarity	NPC221342
0.534	Remote Similarity	NPC476470
0.5333	Remote Similarity	NPC476771
0.5326	Remote Similarity	NPC52550
0.5326	Remote Similarity	NPC488080
0.5326	Remote Similarity	NPC169977
0.5315	Remote Similarity	NPC156785
0.5306	Remote Similarity	NPC39834
0.53	Remote Similarity	NPC154741
0.5275	Remote Similarity	NPC143851
0.5269	Remote Similarity	NPC21100
0.5263	Remote Similarity	NPC605784
0.5258	Remote Similarity	NPC473682
0.5248	Remote Similarity	NPC297503
0.5243	Remote Similarity	NPC85751
0.5243	Remote Similarity	NPC19240
0.5238	Remote Similarity	NPC14187
0.5238	Remote Similarity	NPC81042
0.5221	Remote Similarity	NPC241781
0.5217	Remote Similarity	NPC8573
0.5213	Remote Similarity	NPC235260
0.5213	Remote Similarity	NPC191306
0.5213	Remote Similarity	NPC182121
0.5213	Remote Similarity	NPC155763
0.5213	Remote Similarity	NPC129217
0.5213	Remote Similarity	NPC48093
0.5213	Remote Similarity	NPC488071
0.52	Remote Similarity	NPC129264
0.52	Remote Similarity	NPC33083
0.52	Remote Similarity	NPC470444
0.5196	Remote Similarity	NPC35119
0.5196	Remote Similarity	NPC473327
0.519	Remote Similarity	NPC103342
0.5158	Remote Similarity	NPC85707
0.5158	Remote Similarity	NPC484158
0.5149	Remote Similarity	NPC470125
0.5149	Remote Similarity	NPC296018
0.5149	Remote Similarity	NPC240306
0.5149	Remote Similarity	NPC64425
0.5146	Remote Similarity	NPC205824
0.5146	Remote Similarity	NPC221288
0.5146	Remote Similarity	NPC97119
0.5146	Remote Similarity	NPC194836
0.5146	Remote Similarity	NPC91493
0.5146	Remote Similarity	NPC605081
0.5135	Remote Similarity	NPC488734
0.5135	Remote Similarity	NPC488735
0.5135	Remote Similarity	NPC488739
0.5135	Remote Similarity	NPC488732
0.5135	Remote Similarity	NPC488738
0.5126	Remote Similarity	NPC30011
0.5109	Remote Similarity	NPC104677
0.5104	Remote Similarity	NPC223747
0.5104	Remote Similarity	NPC116458
0.5104	Remote Similarity	NPC246943
0.5096	Remote Similarity	NPC135831
0.5094	Remote Similarity	NPC214621
0.5094	Remote Similarity	NPC34267
0.5089	Remote Similarity	NPC470713
0.5049	Remote Similarity	NPC32641
0.5049	Remote Similarity	NPC256188
0.5049	Remote Similarity	NPC104883
0.5049	Remote Similarity	NPC488679

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC110248 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	4895
0.1-0.2	4164
0.2-0.3	79
0.3-0.4	8
0.4-0.5	3
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
0.5895	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