NPASS Compound

Natural Product: NPC101636

Natural Product ID	NPC101636
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	Apigenin 7-O-Alpha-L-3-O-Acetylrhamnopyranosyl-(1->6)-Beta-D-Glucopyranoside
IUPAC Name	[(2S,3S,4R,5R,6R)-3,5-dihydroxy-2-methyl-6-[[(2R,3S,4S,5R,6S)-3,4,5-trihydroxy-6-[5-hydroxy-2-(4-hydroxyphenyl)-4-oxochromen-7-yl]oxyoxan-2-yl]methoxy]oxan-4-yl] acetate
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL465135
PubChem CID	11250565
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 76 80 0 0 0 0 0 0 0 0999 V2000 -3.6294 1.3620 -3.5646 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2110 0.6989 -2.3547 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.6113 1.2239 -2.0418 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.9168 0.7733 -0.6377 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.9079 -0.7201 -0.6088 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.6027 -1.2028 -1.2058 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.5874 -0.9657 -0.2751 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.0145 -2.1427 0.1485 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9140 -1.9192 1.1593 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.3993 -1.1795 2.3632 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.0732 0.2828 2.3716 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.5932 0.4758 2.2859 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0052 -0.6960 1.5071 C 0 0 2 0 0 0 0 0 0 0 0 0 1.1009 -0.2237 0.8241 O 0 0 0 0 0 0 0 0 0 0 0 0 2.3747 -0.7459 0.9182 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6952 -1.8159 1.7158 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9991 -2.3110 1.7798 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0033 -1.7291 1.0351 C 0 0 0 0 0 0 0 0 0 0 0 0 6.2998 -2.1771 1.0624 C 0 0 0 0 0 0 0 0 0 0 0 0 6.5704 -3.1585 1.8003 O 0 0 0 0 0 0 0 0 0 0 0 0 7.2773 -1.5458 0.2839 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9337 -0.4753 -0.5081 C 0 0 0 0 0 0 0 0 0 0 0 0 7.9145 0.2316 -1.3495 C 0 0 0 0 0 0 0 0 0 0 0 0 7.5352 1.3064 -2.1324 C 0 0 0 0 0 0 0 0 0 0 0 0 8.4065 2.0054 -2.9385 C 0 0 0 0 0 0 0 0 0 0 0 0 9.7236 1.6011 -2.9561 C 0 0 0 0 0 0 0 0 0 0 0 0 10.1325 0.5347 -2.1880 C 0 0 0 0 0 0 0 0 0 0 0 0 9.2099 -0.1467 -1.3826 C 0 0 0 0 0 0 0 0 0 0 0 0 10.6416 2.2720 -3.7515 O 0 0 0 0 0 0 0 0 0 0 0 0 5.6776 -0.0974 -0.4885 O 0 0 0 0 0 0 0 0 0 0 0 0 4.7233 -0.6524 0.2209 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4253 -0.1961 0.1874 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2977 -3.3882 2.5895 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.9349 -1.1264 0.5365 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0431 0.6150 3.5370 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.6630 0.9311 1.2961 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.9601 -1.7623 3.5581 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.3192 -0.6691 -2.4441 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.9500 -1.2329 -1.3648 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.0909 1.3416 -0.1190 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.1774 2.1638 0.9783 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.1176 2.4416 1.5846 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.4908 2.7246 1.4558 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.7137 2.5845 -2.2210 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.6461 0.8924 -3.7590 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.2481 1.2566 -4.4593 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.4207 2.4203 -3.2961 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.5903 0.9401 -1.4736 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.2905 0.6507 -2.7294 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.0824 1.1229 0.0099 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.9242 -1.1289 0.4357 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.6739 -2.3143 -1.3525 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.6632 -2.7283 -0.7234 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.7632 -2.8141 0.6629 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.4209 -2.8796 1.4158 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.5231 -1.2730 2.3692 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.4986 0.6916 3.3242 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.3794 1.4121 1.6936 H 0 0 0 0 0 0 0 0 0 0 0 0 0.1732 -1.5535 2.1640 H 0 0 0 0 0 0 0 0 0 0 0 0 1.9693 -2.3077 2.3127 H 0 0 0 0 0 0 0 0 0 0 0 0 8.2837 -1.9228 0.3297 H 0 0 0 0 0 0 0 0 0 0 0 0 6.5016 1.6203 -2.1158 H 0 0 0 0 0 0 0 0 0 0 0 0 8.0803 2.8538 -3.5493 H 0 0 0 0 0 0 0 0 0 0 0 0 11.1468 0.1987 -2.1817 H 0 0 0 0 0 0 0 0 0 0 0 0 9.5861 -0.9731 -0.8032 H 0 0 0 0 0 0 0 0 0 0 0 0 10.4374 3.2086 -4.0492 H 0 0 0 0 0 0 0 0 0 0 0 0 3.2203 0.6447 -0.4523 H 0 0 0 0 0 0 0 0 0 0 0 0 4.7974 -3.2207 3.4451 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.1354 1.5821 3.7848 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.4654 1.8996 1.3716 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.1839 -1.1382 4.2862 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.6451 -1.9172 -2.0235 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.4854 2.7894 2.5622 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.2744 1.9889 1.1703 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.7185 3.6889 0.9978 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.1897 3.0191 -1.5088 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 1 0 3 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 10 11 1 0 11 12 1 0 12 13 1 0 13 14 1 0 14 15 1 0 15 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 2 0 22 23 1 0 23 24 2 0 24 25 1 0 25 26 2 0 26 27 1 0 27 28 2 0 26 29 1 0 22 30 1 0 30 31 1 0 31 32 2 0 17 33 1 0 13 34 1 0 12 35 1 0 11 36 1 0 10 37 1 0 6 38 1 0 5 39 1 0 4 40 1 0 40 41 1 0 41 42 2 0 41 43 1 0 3 44 1 0 38 2 1 0 34 9 1 0 32 15 1 0 31 18 1 0 28 23 1 0 1 45 1 0 1 46 1 0 1 47 1 0 2 48 1 1 3 49 1 6 4 50 1 1 5 51 1 1 6 52 1 6 8 53 1 0 8 54 1 0 9 55 1 1 10 56 1 1 11 57 1 1 12 58 1 6 13 59 1 1 16 60 1 0 21 61 1 0 24 62 1 0 25 63 1 0 27 64 1 0 28 65 1 0 29 66 1 0 32 67 1 0 33 68 1 0 35 69 1 0 36 70 1 0 37 71 1 0 39 72 1 0 43 73 1 0 43 74 1 0 43 75 1 0 44 76 1 0 M END

Standard InCHIKey	WXBYVUCALCQKLS-MRBYITRJSA-N
Standard InCHI	InChI=1S/C29H32O15/c1-11-22(34)27(41-12(2)30)26(38)28(40-11)39-10-20-23(35)24(36)25(37)29(44-20)42-15-7-16(32)21-17(33)9-18(43-19(21)8-15)13-3-5-14(31)6-4-13/h3-9,11,20,22-29,31-32,34-38H,10H2,1-2H3/t11-,20+,22-,23+,24-,25+,26+,27+,28+,29+/m0/s1
SMILES	C[C@H]1[C@@H]([C@H]([C@H]([C@H](OC[C@@H]2[C@H]([C@@H]([C@H]([C@H](Oc3cc(c4c(=O)cc(c5ccc(cc5)O)oc4c3)O)O2)O)O)O)O1)O)OC(=O)C)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	620.17	Volume:	575.483 ? Van der Waals volume.
Dense:	1.078	LogP:	1.061 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	1.531 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-3.239 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	8.0	Rigid Bonds:	31.0
TPSA:	235.04 ? Topological Polar Surface Area.	H-Bond Acceptor:	15.0
H-Bond Donor:	7.0	Rings:	5.0
Heavy Atoms:	15.0

MedChem Properties

QED Drug-Likeness Score:	0.165	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.728	Fsp³:	0.448
MCE-18:	118.19 ? 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:	0.637	Fluc inhibitor:	0.349 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.934 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.594 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.085	Promiscuous compounds:	0.313

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-6.399	MDCK Permeability:	-5.161
Pgp-inhibitor:	0.0	Pgp-substrate:	0.886
PAMPA:	1.0 ? 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):	0.541
20% Bioavailability (F20%):	0.541	30% Bioavailability (F30%):	0.991
50% Bioavailability (F50%):	0.998

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.002	MRP1:	0.462
Plasma Protein Binding (PPB):	83.463%	Volume Distribution (VD):	-0.003
Fu:	15.201% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.998
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.407
BSEP inhibitor:	0.007

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.002
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.013	CYP2C9-substrate:	0.021
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.608
CYP3A4-inhibitor:	0.0	CYP3A4-substrate:	0.897
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.999
HLM stability:	0.073 ? 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):

1.637

Half-life (T1/2):

3.967

ADMET: Toxicity

hERG Blockers:	0.028	hERG Blockers (10um):	0.237
Human Hepatotoxicity (H-HT):	0.42	Drug-induced Liver Injury (DILI):	0.987
AMES Toxicity:	0.825	Rat Oral Acute Toxicity:	0.032
Maximum Recommended Daily Dose:	0.112	Skin Sensitization:	0.911
Carcinogencity:	0.112	Eye Corrosion:	0.0
Eye Irritation:	0.571	Respiratory Toxicity:	0.016
Drug-induced Neurotoxicity:	0.002	Ototoxicity:	0.709
Hematotoxicity:	0.049	Drug-induced Nephrotoxicity:	0.491
Genotoxicity:	0.844	RPMI-8226 Immunitoxicity:	0.152
A549 Cytotoxicity:	0.36	Hek293 Cytotoxicity:	0.509
BCF:	0.42 ? 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:	3.122 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.669 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	3.723 ? 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
NPO15289	Scoparia dulcis	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12880314]
NPO15289	Scoparia dulcis	Species	Plantaginaceae	Eukaryota	n.a.	whole plant	n.a.	PMID[1294695]
NPO15289	Scoparia dulcis	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15104516]
NPO15289	Scoparia dulcis	Species	Plantaginaceae	Eukaryota	leaves and twigs	Taiwan	n.a.	PMID[1659612]
NPO15289	Scoparia dulcis	Species	Plantaginaceae	Eukaryota	aerial parts	Nanning, Guangxi Zhuang Autonomous Region, Peoples Republic of China	2012-OCT	PMID[24955889]
NPO15289	Scoparia dulcis	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO15289	Scoparia dulcis	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO15289	Scoparia dulcis	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO15289	Scoparia dulcis	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO15289	Scoparia dulcis	Species	Plantaginaceae	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
Activity	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
NPT681	Cell line	PC-12	Rattus norvegicus	Activity	=	16.1	%	PubChem BioAssay data set

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 NPC101636 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	17592
0.1-0.2	28663
0.2-0.3	2658
0.3-0.4	585
0.4-0.5	227
0.5-0.6	90
0.6-0.7	25
0.7-0.8	0
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.8161	Intermediate Similarity	NPC44931
0.7849	Intermediate Similarity	NPC298171
0.7283	Intermediate Similarity	NPC22062
0.7283	Intermediate Similarity	NPC473634
0.7283	Intermediate Similarity	NPC210073
0.7283	Intermediate Similarity	NPC138811
0.7255	Intermediate Similarity	NPC488086
0.7083	Intermediate Similarity	NPC488089
0.6977	Remote Similarity	NPC331652
0.6947	Remote Similarity	NPC64051
0.6804	Remote Similarity	NPC209296
0.6735	Remote Similarity	NPC270675
0.6735	Remote Similarity	NPC195685
0.6667	Remote Similarity	NPC27942
0.6633	Remote Similarity	NPC473623
0.6535	Remote Similarity	NPC472994
0.6531	Remote Similarity	NPC65711
0.6517	Remote Similarity	NPC39360
0.6517	Remote Similarity	NPC29763
0.6517	Remote Similarity	NPC210003
0.6495	Remote Similarity	NPC186816
0.6316	Remote Similarity	NPC172807
0.63	Remote Similarity	NPC229409
0.6286	Remote Similarity	NPC472993
0.6239	Remote Similarity	NPC298666
0.6154	Remote Similarity	NPC19709
0.6122	Remote Similarity	NPC67105
0.61	Remote Similarity	NPC46202
0.6095	Remote Similarity	NPC11468
0.6055	Remote Similarity	NPC488088
0.6042	Remote Similarity	NPC190003
0.6019	Remote Similarity	NPC479765
0.6	Remote Similarity	NPC204693
0.5981	Remote Similarity	NPC473278
0.5938	Remote Similarity	NPC220169
0.59	Remote Similarity	NPC473512
0.59	Remote Similarity	NPC65003
0.59	Remote Similarity	NPC129827
0.5851	Remote Similarity	NPC181712
0.5818	Remote Similarity	NPC488087
0.5745	Remote Similarity	NPC95090
0.5745	Remote Similarity	NPC27408
0.5745	Remote Similarity	NPC189142
0.5745	Remote Similarity	NPC77660
0.5743	Remote Similarity	NPC303913
0.5741	Remote Similarity	NPC189564
0.5699	Remote Similarity	NPC473043
0.5676	Remote Similarity	NPC488083
0.5673	Remote Similarity	NPC210961
0.5657	Remote Similarity	NPC211594
0.5644	Remote Similarity	NPC227508
0.5638	Remote Similarity	NPC108831
0.5638	Remote Similarity	NPC182634
0.5636	Remote Similarity	NPC473644
0.5607	Remote Similarity	NPC179862
0.56	Remote Similarity	NPC254540
0.5586	Remote Similarity	NPC311850
0.5575	Remote Similarity	NPC68592
0.5566	Remote Similarity	NPC80068
0.5556	Remote Similarity	NPC262222
0.5524	Remote Similarity	NPC483707
0.5524	Remote Similarity	NPC606657
0.551	Remote Similarity	NPC243930
0.551	Remote Similarity	NPC601144
0.5495	Remote Similarity	NPC25523
0.5474	Remote Similarity	NPC261866
0.5474	Remote Similarity	NPC249281
0.5455	Remote Similarity	NPC311830
0.5455	Remote Similarity	NPC607707
0.5421	Remote Similarity	NPC475382
0.5408	Remote Similarity	NPC282169
0.5405	Remote Similarity	NPC292019
0.5405	Remote Similarity	NPC202908
0.54	Remote Similarity	NPC276377
0.5361	Remote Similarity	NPC46420
0.5354	Remote Similarity	NPC22832
0.5345	Remote Similarity	NPC471030
0.534	Remote Similarity	NPC173582
0.534	Remote Similarity	NPC265885
0.534	Remote Similarity	NPC181465
0.534	Remote Similarity	NPC215710
0.534	Remote Similarity	NPC473438
0.534	Remote Similarity	NPC253788
0.5333	Remote Similarity	NPC475366
0.5327	Remote Similarity	NPC142142
0.5288	Remote Similarity	NPC479405
0.5278	Remote Similarity	NPC477629
0.5259	Remote Similarity	NPC198199
0.5258	Remote Similarity	NPC323593
0.5258	Remote Similarity	NPC203500
0.5254	Remote Similarity	NPC120952
0.5243	Remote Similarity	NPC295613
0.5243	Remote Similarity	NPC473657
0.5238	Remote Similarity	NPC122809
0.5238	Remote Similarity	NPC115674
0.5238	Remote Similarity	NPC479404
0.5234	Remote Similarity	NPC72016
0.5225	Remote Similarity	NPC121703
0.52	Remote Similarity	NPC80188
0.5196	Remote Similarity	NPC477848
0.5192	Remote Similarity	NPC275454
0.5189	Remote Similarity	NPC64425
0.5185	Remote Similarity	NPC479766
0.5176	Remote Similarity	NPC234133
0.5155	Remote Similarity	NPC238376
0.5149	Remote Similarity	NPC116458
0.5149	Remote Similarity	NPC246943
0.5143	Remote Similarity	NPC65563
0.5143	Remote Similarity	NPC470949
0.5143	Remote Similarity	NPC150164
0.5133	Remote Similarity	NPC480796
0.5102	Remote Similarity	NPC93337
0.5102	Remote Similarity	NPC297987
0.5102	Remote Similarity	NPC146792
0.5096	Remote Similarity	NPC187379
0.5094	Remote Similarity	NPC473571
0.5094	Remote Similarity	NPC110941
0.5091	Remote Similarity	NPC470449
0.5088	Remote Similarity	NPC480441
0.5051	Remote Similarity	NPC105025
0.5047	Remote Similarity	NPC284277
0.5047	Remote Similarity	NPC475497
0.5045	Remote Similarity	NPC135358

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC101636 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	5009
0.1-0.2	4075
0.2-0.3	55
0.3-0.4	6
0.4-0.5	0
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
0.6804	Remote Similarity	NPD7054	Phase 4
0.5566	Remote Similarity	NPD7251	Phase 2
0.5364	Remote Similarity	NPD7808	Phase 3
0.5089	Remote Similarity	NPD7472	Pre-clinical

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