NPASS Compound

Natural Product: NPC475366

Natural Product ID	NPC475366
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	5,7,4'-Trimethoxyflavone-7-O-Glucorhamnoside
IUPAC Name	2-(3,4-dimethoxyphenyl)-5-methoxy-7-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-[[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxymethyl]oxan-2-yl]oxychromen-4-one
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL504375
PubChem CID	44575347
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 81 85 0 0 0 0 0 0 0 0999 V2000 -0.2395 3.5189 2.9977 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5125 3.0545 2.5863 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.5456 1.9914 1.6648 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3953 1.4220 1.1793 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4341 0.3730 0.2698 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7529 -0.1398 -0.1666 O 0 0 0 0 0 0 0 0 0 0 0 0 0.9815 -1.1880 -1.0694 C 0 0 2 0 0 0 0 0 0 0 0 0 1.6610 -2.1798 -0.3858 O 0 0 0 0 0 0 0 0 0 0 0 0 3.0197 -2.0763 -0.3465 C 0 0 2 0 0 0 0 0 0 0 0 0 3.4304 -0.9228 0.5260 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8160 -0.7855 0.5924 O 0 0 0 0 0 0 0 0 0 0 0 0 5.1901 0.2803 1.3997 C 0 0 1 0 0 0 0 0 0 0 0 0 5.9646 -0.2012 2.4173 O 0 0 0 0 0 0 0 0 0 0 0 0 7.3186 -0.1636 2.2352 C 0 0 2 0 0 0 0 0 0 0 0 0 7.9906 0.9982 2.9391 C 0 0 0 0 0 0 0 0 0 0 0 0 7.7566 -0.2523 0.8117 C 0 0 2 0 0 0 0 0 0 0 0 0 7.2204 0.9093 0.0423 C 0 0 1 0 0 0 0 0 0 0 0 0 5.8591 1.2977 0.5113 C 0 0 1 0 0 0 0 0 0 0 0 0 4.9971 1.5495 -0.5685 O 0 0 0 0 0 0 0 0 0 0 0 0 8.1090 1.9980 0.0348 O 0 0 0 0 0 0 0 0 0 0 0 0 7.3365 -1.4283 0.2160 O 0 0 0 0 0 0 0 0 0 0 0 0 3.6644 -2.0231 -1.7088 C 0 0 2 0 0 0 0 0 0 0 0 0 2.6523 -1.6753 -2.7836 C 0 0 1 0 0 0 0 0 0 0 0 0 1.6840 -0.6443 -2.2720 C 0 0 1 0 0 0 0 0 0 0 0 0 0.7457 -0.4347 -3.2808 O 0 0 0 0 0 0 0 0 0 0 0 0 3.2729 -1.2573 -3.9562 O 0 0 0 0 0 0 0 0 0 0 0 0 4.2956 -3.2311 -1.9864 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.6532 -0.0938 -0.1433 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8645 0.4501 0.3196 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7533 1.4861 1.2184 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9321 2.0290 1.6807 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8726 2.9701 2.4970 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.1226 1.5008 1.2144 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1774 0.4635 0.3149 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0087 -0.0264 -0.1015 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.4214 -0.1174 -0.1973 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.3938 -1.1612 -1.0988 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.5570 -1.7112 -1.5847 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.7982 -1.2150 -1.1675 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.8367 -0.1735 -0.2681 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.6275 0.3627 0.2064 C 0 0 0 0 0 0 0 0 0 0 0 0 -10.0686 0.3120 0.1398 O 0 0 0 0 0 0 0 0 0 0 0 0 -10.1652 1.3959 1.0749 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.9662 -1.7736 -1.6610 O 0 0 0 0 0 0 0 0 0 0 0 0 -9.9046 -2.8459 -2.5870 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2991 4.2723 3.7908 H 0 0 0 0 0 0 0 0 0 0 0 0 0.3276 3.9750 2.1506 H 0 0 0 0 0 0 0 0 0 0 0 0 0.4034 2.6874 3.3670 H 0 0 0 0 0 0 0 0 0 0 0 0 0.5691 1.8164 1.5285 H 0 0 0 0 0 0 0 0 0 0 0 0 0.0048 -1.6090 -1.4015 H 0 0 0 0 0 0 0 0 0 0 0 0 3.4018 -2.9920 0.1604 H 0 0 0 0 0 0 0 0 0 0 0 0 3.0812 -1.0257 1.5660 H 0 0 0 0 0 0 0 0 0 0 0 0 3.0505 0.0542 0.1632 H 0 0 0 0 0 0 0 0 0 0 0 0 4.2356 0.7381 1.7794 H 0 0 0 0 0 0 0 0 0 0 0 0 7.7320 -1.0809 2.7457 H 0 0 0 0 0 0 0 0 0 0 0 0 7.4304 1.9318 2.9029 H 0 0 0 0 0 0 0 0 0 0 0 0 8.0797 0.7344 4.0320 H 0 0 0 0 0 0 0 0 0 0 0 0 9.0324 1.0637 2.5573 H 0 0 0 0 0 0 0 0 0 0 0 0 8.8728 -0.2353 0.8032 H 0 0 0 0 0 0 0 0 0 0 0 0 7.1290 0.5976 -1.0377 H 0 0 0 0 0 0 0 0 0 0 0 0 5.9172 2.2535 1.0759 H 0 0 0 0 0 0 0 0 0 0 0 0 5.4195 1.2114 -1.3967 H 0 0 0 0 0 0 0 0 0 0 0 0 9.0224 1.6369 -0.0834 H 0 0 0 0 0 0 0 0 0 0 0 0 7.8345 -1.6538 -0.5992 H 0 0 0 0 0 0 0 0 0 0 0 0 4.4488 -1.2405 -1.6751 H 0 0 0 0 0 0 0 0 0 0 0 0 2.1054 -2.6107 -3.0185 H 0 0 0 0 0 0 0 0 0 0 0 0 2.1759 0.3251 -2.0501 H 0 0 0 0 0 0 0 0 0 0 0 0 0.1252 -1.2309 -3.2476 H 0 0 0 0 0 0 0 0 0 0 0 0 4.1761 -0.9176 -3.7230 H 0 0 0 0 0 0 0 0 0 0 0 0 4.9388 -3.1416 -2.7430 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.7644 -0.9067 -0.8494 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.0461 1.9352 1.5840 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.4574 -1.5624 -1.4367 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.4847 -2.5260 -2.2884 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.7457 1.1694 0.9023 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.6350 1.1555 2.0187 H 0 0 0 0 0 0 0 0 0 0 0 0 -11.2230 1.6653 1.2507 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.6458 2.3052 0.6631 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.3013 -2.5636 -3.4716 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.4657 -3.7222 -2.0422 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.9142 -3.1511 -2.9162 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 1 0 6 7 1 0 7 8 1 0 8 9 1 0 9 10 1 0 10 11 1 0 11 12 1 0 12 13 1 0 13 14 1 0 14 15 1 0 14 16 1 0 16 17 1 0 17 18 1 0 18 19 1 0 17 20 1 0 16 21 1 0 9 22 1 0 22 23 1 0 23 24 1 0 24 25 1 0 23 26 1 0 22 27 1 0 5 28 2 0 28 29 1 0 29 30 2 0 30 31 1 0 31 32 2 0 31 33 1 0 33 34 2 0 34 35 1 0 34 36 1 0 36 37 2 0 37 38 1 0 38 39 2 0 39 40 1 0 40 41 2 0 40 42 1 0 42 43 1 0 39 44 1 0 44 45 1 0 30 3 1 0 41 36 1 0 24 7 1 0 35 29 1 0 18 12 1 0 1 46 1 0 1 47 1 0 1 48 1 0 4 49 1 0 7 50 1 6 9 51 1 1 10 52 1 0 10 53 1 0 12 54 1 1 14 55 1 1 15 56 1 0 15 57 1 0 15 58 1 0 16 59 1 1 17 60 1 6 18 61 1 1 19 62 1 0 20 63 1 0 21 64 1 0 22 65 1 1 23 66 1 6 24 67 1 1 25 68 1 0 26 69 1 0 27 70 1 0 28 71 1 0 33 72 1 0 37 73 1 0 38 74 1 0 41 75 1 0 43 76 1 0 43 77 1 0 43 78 1 0 45 79 1 0 45 80 1 0 45 81 1 0 M END

Standard InCHIKey	BZSRRACZBYSKRB-UPMDXQIVSA-N
Standard InCHI	InChI=1S/C30H36O15/c1-12-23(32)25(34)27(36)29(42-12)41-11-21-24(33)26(35)28(37)30(45-21)43-14-8-19(40-4)22-15(31)10-17(44-20(22)9-14)13-5-6-16(38-2)18(7-13)39-3/h5-10,12,21,23-30,32-37H,11H2,1-4H3/t12-,21-,23-,24-,25+,26+,27-,28-,29+,30-/m1/s1
SMILES	COc1cc(O[C@@H]2O[C@H](CO[C@H]3O[C@H](C)[C@H]([C@@H]([C@H]3O)O)O)[C@H]([C@@H]([C@H]2O)O)O)cc2c1c(=O)cc(o2)c1ccc(c(c1)OC)OC

Calculated Properties

Physi-Chem Properties

Molecular Weight:	636.21	Volume:	595.415 ? Van der Waals volume.
Dense:	1.069	LogP:	1.532 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	1.833 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-3.05 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	9.0	Rigid Bonds:	30.0
TPSA:	216.2 ? Topological Polar Surface Area.	H-Bond Acceptor:	15.0
H-Bond Donor:	6.0	Rings:	5.0
Heavy Atoms:	15.0

MedChem Properties

QED Drug-Likeness Score:	0.175	GASA:	0.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.614	Fsp³:	0.5
MCE-18:	117.111 ? 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:	0	PAINS Alert:	0
Colloidal aggregators:	0.592	Fluc inhibitor:	0.238 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.899 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.559 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.033	Promiscuous compounds:	0.157

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.903	MDCK Permeability:	-5.138
Pgp-inhibitor:	0.005	Pgp-substrate:	0.768
PAMPA:	0.957 ? 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):	0.37
20% Bioavailability (F20%):	0.015	30% Bioavailability (F30%):	0.42
50% Bioavailability (F50%):	0.937

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.062
Plasma Protein Binding (PPB):	81.262%	Volume Distribution (VD):	-0.25
Fu:	16.476% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.957
BSEP inhibitor:	0.948

ADMET: Metabolism

CYP1A2-inhibitor:	0.006	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:	0.008
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.127
HLM stability:	0.002 ? 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):

1.531

Half-life (T1/2):

6.197

ADMET: Toxicity

hERG Blockers:	0.034	hERG Blockers (10um):	0.201
Human Hepatotoxicity (H-HT):	0.413	Drug-induced Liver Injury (DILI):	0.936
AMES Toxicity:	0.836	Rat Oral Acute Toxicity:	0.016
Maximum Recommended Daily Dose:	0.048	Skin Sensitization:	0.863
Carcinogencity:	0.095	Eye Corrosion:	0.0
Eye Irritation:	0.112	Respiratory Toxicity:	0.01
Drug-induced Neurotoxicity:	0.004	Ototoxicity:	0.954
Hematotoxicity:	0.321	Drug-induced Nephrotoxicity:	0.803
Genotoxicity:	0.64	RPMI-8226 Immunitoxicity:	0.219
A549 Cytotoxicity:	0.06	Hek293 Cytotoxicity:	0.228
BCF:	0.184 ? 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:	2.996 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.392 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	3.62 ? 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
NPO23424	Dirca palustris	Species	Thymelaeaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10579873]
NPO23424	Dirca palustris	Species	Thymelaeaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26225905]
NPO23424	Dirca palustris	Species	Thymelaeaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO23424	Dirca palustris	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
Inhibition	1

Activity Type	# Activity
Others	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
NPT35	Others	n.a.	n.a.	Inhibition	=	67.0	%	PMID[25847767]

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 NPC475366 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	19578
0.1-0.2	26526
0.2-0.3	2919
0.3-0.4	594
0.4-0.5	187
0.5-0.6	36
0.6-0.7	10
0.7-0.8	1
0.8-0.85	1
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.8571	High Similarity	NPC475497
0.814	Intermediate Similarity	NPC284277
0.7471	Intermediate Similarity	NPC473657
0.7079	Intermediate Similarity	NPC295613
0.7	Intermediate Similarity	NPC15358
0.6923	Remote Similarity	NPC473512
0.686	Remote Similarity	NPC182045
0.6739	Remote Similarity	NPC22062
0.6739	Remote Similarity	NPC473634
0.6739	Remote Similarity	NPC138811
0.6667	Remote Similarity	NPC204693
0.6559	Remote Similarity	NPC129827
0.6458	Remote Similarity	NPC209296
0.6211	Remote Similarity	NPC210073
0.6105	Remote Similarity	NPC44931
0.5825	Remote Similarity	NPC244875
0.5778	Remote Similarity	NPC110349
0.5743	Remote Similarity	NPC488089
0.5696	Remote Similarity	NPC70853
0.5652	Remote Similarity	NPC610763
0.5644	Remote Similarity	NPC473623
0.5612	Remote Similarity	NPC67105
0.5556	Remote Similarity	NPC475155
0.551	Remote Similarity	NPC187379
0.549	Remote Similarity	NPC483707
0.5474	Remote Similarity	NPC243930
0.5474	Remote Similarity	NPC284960
0.5472	Remote Similarity	NPC11468
0.5464	Remote Similarity	NPC211594
0.5455	Remote Similarity	NPC227508
0.5417	Remote Similarity	NPC607707
0.5333	Remote Similarity	NPC101636
0.5273	Remote Similarity	NPC311850
0.5253	Remote Similarity	NPC254540
0.5243	Remote Similarity	NPC470443
0.5204	Remote Similarity	NPC61791
0.5196	Remote Similarity	NPC186816
0.5192	Remote Similarity	NPC473327
0.5182	Remote Similarity	NPC473644
0.5161	Remote Similarity	NPC114740
0.5152	Remote Similarity	NPC172807
0.5146	Remote Similarity	NPC126784
0.5146	Remote Similarity	NPC241423
0.5133	Remote Similarity	NPC68592
0.5102	Remote Similarity	NPC99957
0.5102	Remote Similarity	NPC293004
0.5088	Remote Similarity	NPC198199
0.5052	Remote Similarity	NPC609451
0.505	Remote Similarity	NPC414831
0.5049	Remote Similarity	NPC473571
0.5049	Remote Similarity	NPC110941

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC475366 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	4890
0.1-0.2	4170
0.2-0.3	78
0.3-0.4	6
0.4-0.5	1
0.5-0.6	3
0.6-0.7	1
0.7-0.8	1
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
0.7447	Intermediate Similarity	NPD7472	Pre-clinical
0.6458	Remote Similarity	NPD7054	Phase 4
0.5769	Remote Similarity	NPD7808	Phase 3
0.5227	Remote Similarity	NPD3817	Phase 3
0.5094	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