NPASS Compound

Natural Product: NPC158034

Natural Product ID	NPC158034
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	XXUHDKDDHQURGH-PUIBNRJISA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	14825846
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 5.3877 2.4832 1.7691 C 0 0 0 0 0 0 0 0 0 0 0 0 6.4949 1.9174 1.1215 O 0 0 0 0 0 0 0 0 0 0 0 0 6.2909 0.8934 0.2211 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0320 0.4105 -0.0607 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8539 -0.6311 -0.9802 C 0 0 0 0 0 0 0 0 0 0 0 0 5.9790 -1.1301 -1.5694 C 0 0 0 0 0 0 0 0 0 0 0 0 7.2654 -0.6632 -1.3055 C 0 0 0 0 0 0 0 0 0 0 0 0 7.4027 0.3607 -0.3969 C 0 0 0 0 0 0 0 0 0 0 0 0 8.6843 0.8449 -0.1168 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4851 -1.1179 -1.2527 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2807 -2.1379 -2.1478 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0084 -2.6129 -2.4213 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7444 -3.5278 -3.2143 O 0 0 0 0 0 0 0 0 0 0 0 0 0.9610 -1.9917 -1.7334 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3359 -2.3927 -1.9371 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3492 -1.7715 -1.2535 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1536 -0.7487 -0.3549 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1771 -0.3553 -0.1620 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2072 -0.9693 -0.8412 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4635 -0.5734 -0.6371 O 0 0 0 0 0 0 0 0 0 0 0 0 0.4618 0.6711 0.7292 O 0 0 0 0 0 0 0 0 0 0 0 0 0.5218 2.0249 0.3916 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1661 -0.1163 0.3388 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.5297 -0.3670 0.2784 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.9957 -0.7998 1.6631 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.4374 0.4384 2.3896 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.6763 1.0062 1.7081 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.5782 0.7179 0.2443 C 0 0 1 0 0 0 0 0 0 0 0 0 -6.3609 1.7124 -0.5895 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.8671 2.9896 -0.4378 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.2651 0.7414 -0.1616 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.8393 0.4730 2.2743 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4139 1.3818 2.2963 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.9977 -1.7573 1.5783 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.5853 -3.4348 -2.8468 O 0 0 0 0 0 0 0 0 0 0 0 0 5.7252 3.1141 2.6340 H 0 0 0 0 0 0 0 0 0 0 0 0 4.6886 1.7099 2.1819 H 0 0 0 0 0 0 0 0 0 0 0 0 4.8426 3.1085 1.0251 H 0 0 0 0 0 0 0 0 0 0 0 0 4.1484 0.8150 0.4134 H 0 0 0 0 0 0 0 0 0 0 0 0 5.8881 -1.9320 -2.2831 H 0 0 0 0 0 0 0 0 0 0 0 0 8.1135 -1.1206 -1.8231 H 0 0 0 0 0 0 0 0 0 0 0 0 9.4070 0.1181 -0.0488 H 0 0 0 0 0 0 0 0 0 0 0 0 4.0935 -2.6227 -2.6840 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.3622 -2.1208 -1.4451 H 0 0 0 0 0 0 0 0 0 0 0 0 0.3002 2.6212 1.3103 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.1786 2.3378 -0.3891 H 0 0 0 0 0 0 0 0 0 0 0 0 1.5789 2.2653 0.1343 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.7508 -1.1791 -0.4264 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.1359 -1.2715 2.1616 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.6267 0.2709 3.4727 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.6980 2.1046 1.8607 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.0617 -0.2771 0.0628 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.3979 1.3645 -1.6415 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.4331 1.7199 -0.2462 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.0365 3.0758 -0.9347 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.5083 1.1725 2.4487 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.5199 2.0779 2.9952 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.7086 -2.6419 1.9071 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.5185 -3.4222 -3.2688 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 2 0 6 7 1 0 7 8 2 0 8 9 1 0 5 10 1 0 10 11 2 0 11 12 1 0 12 13 2 0 12 14 1 0 14 15 2 0 15 16 1 0 16 17 2 0 17 18 1 0 18 19 2 0 19 20 1 0 18 21 1 0 21 22 1 0 17 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 28 31 1 0 27 32 1 0 26 33 1 0 25 34 1 0 15 35 1 0 8 3 1 0 20 10 1 0 31 24 1 0 19 14 1 0 1 36 1 0 1 37 1 0 1 38 1 0 4 39 1 0 6 40 1 0 7 41 1 0 9 42 1 0 11 43 1 0 16 44 1 0 22 45 1 0 22 46 1 0 22 47 1 0 24 48 1 6 25 49 1 1 26 50 1 1 27 51 1 6 28 52 1 1 29 53 1 0 29 54 1 0 30 55 1 0 32 56 1 0 33 57 1 0 34 58 1 0 35 59 1 0 M END

Standard InCHIKey	XXUHDKDDHQURGH-PUIBNRJISA-N
Standard InCHI	InChI=1S/C23H24O12/c1-31-14-5-9(3-4-10(14)25)13-6-11(26)17-12(27)7-15(21(32-2)22(17)33-13)34-23-20(30)19(29)18(28)16(8-24)35-23/h3-7,16,18-20,23-25,27-30H,8H2,1-2H3/t16-,18-,19+,20-,23-/m1/s1
SMILES	COc1cc(ccc1O)c1cc(=O)c2c(cc(c(c2o1)OC)O[C@H]1[C@@H]([C@H]([C@@H]([C@@H](CO)O1)O)O)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	492.13	Volume:	456.529 ? Van der Waals volume.
Dense:	1.078	LogP:	1.067 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	1.447 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-3.315 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	6.0	Rigid Bonds:	24.0
TPSA:	188.51 ? Topological Polar Surface Area.	H-Bond Acceptor:	12.0
H-Bond Donor:	6.0	Rings:	4.0
Heavy Atoms:	12.0

MedChem Properties

QED Drug-Likeness Score:	0.272	GASA:	0.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	3.997	Fsp³:	0.348
MCE-18:	89.71 ? 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:	Rejected	BMS Rule:	0
Chelating Alert:	1	PAINS Alert:	0
Colloidal aggregators:	0.576	Fluc inhibitor:	0.276 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.962 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.912 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.091	Promiscuous compounds:	0.669

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-6.097	MDCK Permeability:	-5.287
Pgp-inhibitor:	0.002	Pgp-substrate:	0.542
PAMPA:	0.87 ? 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):	0.492
20% Bioavailability (F20%):	0.138	30% Bioavailability (F30%):	0.947
50% Bioavailability (F50%):	0.99

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.006	MRP1:	0.523
Plasma Protein Binding (PPB):	84.615%	Volume Distribution (VD):	-0.093
Fu:	14.434% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.999
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.776
BSEP inhibitor:	0.04

ADMET: Metabolism

CYP1A2-inhibitor:	0.002	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.003	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.005	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.008
CYP3A4-inhibitor:	0.001	CYP3A4-substrate:	0.001
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.063
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):

2.951

Half-life (T1/2):

3.928

ADMET: Toxicity

hERG Blockers:	0.014	hERG Blockers (10um):	0.118
Human Hepatotoxicity (H-HT):	0.581	Drug-induced Liver Injury (DILI):	0.948
AMES Toxicity:	0.884	Rat Oral Acute Toxicity:	0.049
Maximum Recommended Daily Dose:	0.108	Skin Sensitization:	0.992
Carcinogencity:	0.392	Eye Corrosion:	0.0
Eye Irritation:	0.356	Respiratory Toxicity:	0.077
Drug-induced Neurotoxicity:	0.004	Ototoxicity:	0.77
Hematotoxicity:	0.266	Drug-induced Nephrotoxicity:	0.437
Genotoxicity:	0.9	RPMI-8226 Immunitoxicity:	0.171
A549 Cytotoxicity:	0.389	Hek293 Cytotoxicity:	0.5
BCF:	0.462 ? 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:	3.02 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.282 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	3.571 ? 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
NPO16297	Gentiana arisanensis	Species	Gentianaceae	Eukaryota	Whole Plant	Yu Shieh, Chiayi Hsieh, Taiwan	1994-APR	PMID[9287421]
NPO18413	Eucalyptus ovata	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO12948	Solanum dulcamara	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO15721	Derris reticulata	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO16297	Gentiana arisanensis	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO16918	Ballota lanata	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO12948	Solanum dulcamara	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO12948	Solanum dulcamara	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO12948	Solanum dulcamara	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO16297	Gentiana arisanensis	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15721	Derris reticulata	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16918	Ballota lanata	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18413	Eucalyptus ovata	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12948	Solanum dulcamara	Species	Solanaceae	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 NPC158034 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	22102
0.1-0.2	23732
0.2-0.3	2747
0.3-0.4	916
0.4-0.5	267
0.5-0.6	63
0.6-0.7	18
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
0.7625	Intermediate Similarity	NPC311830
0.7407	Intermediate Similarity	NPC602805
0.7073	Intermediate Similarity	NPC601144
0.6667	Remote Similarity	NPC601710
0.6395	Remote Similarity	NPC607707
0.6279	Remote Similarity	NPC243930
0.6136	Remote Similarity	NPC488072
0.6136	Remote Similarity	NPC601586
0.6118	Remote Similarity	NPC105025
0.6092	Remote Similarity	NPC22832
0.6071	Remote Similarity	NPC39360
0.6071	Remote Similarity	NPC29763
0.6071	Remote Similarity	NPC210003
0.6047	Remote Similarity	NPC201292
0.6023	Remote Similarity	NPC88023
0.6023	Remote Similarity	NPC309025
0.6	Remote Similarity	NPC93337
0.6	Remote Similarity	NPC95090
0.6	Remote Similarity	NPC27408
0.6	Remote Similarity	NPC189142
0.6	Remote Similarity	NPC77660
0.5977	Remote Similarity	NPC609451
0.5955	Remote Similarity	NPC203050
0.5955	Remote Similarity	NPC225434
0.593	Remote Similarity	NPC45638
0.5909	Remote Similarity	NPC101026
0.5909	Remote Similarity	NPC488077
0.5833	Remote Similarity	NPC93099
0.5814	Remote Similarity	NPC259152
0.5778	Remote Similarity	NPC469931
0.5773	Remote Similarity	NPC195257
0.5761	Remote Similarity	NPC480466
0.5747	Remote Similarity	NPC186807
0.573	Remote Similarity	NPC605067
0.5698	Remote Similarity	NPC58053
0.5698	Remote Similarity	NPC261866
0.5667	Remote Similarity	NPC206123
0.5652	Remote Similarity	NPC472607
0.5632	Remote Similarity	NPC146792
0.5568	Remote Similarity	NPC58716
0.5556	Remote Similarity	NPC197285
0.5556	Remote Similarity	NPC606560
0.5543	Remote Similarity	NPC4390
0.5517	Remote Similarity	NPC210042
0.5506	Remote Similarity	NPC222936
0.5495	Remote Similarity	NPC111249
0.5444	Remote Similarity	NPC191306
0.5393	Remote Similarity	NPC84362
0.5393	Remote Similarity	NPC610763
0.5385	Remote Similarity	NPC128863
0.5341	Remote Similarity	NPC45618
0.5341	Remote Similarity	NPC44558
0.5341	Remote Similarity	NPC83283
0.5341	Remote Similarity	NPC143851
0.5333	Remote Similarity	NPC198324
0.5319	Remote Similarity	NPC480463
0.5316	Remote Similarity	NPC227325
0.5269	Remote Similarity	NPC48773
0.5253	Remote Similarity	NPC124155
0.5222	Remote Similarity	NPC603655
0.5217	Remote Similarity	NPC284960
0.5217	Remote Similarity	NPC486578
0.5165	Remote Similarity	NPC182045
0.5165	Remote Similarity	NPC117260
0.5125	Remote Similarity	NPC137062
0.5125	Remote Similarity	NPC152166
0.5111	Remote Similarity	NPC282987
0.5111	Remote Similarity	NPC8573
0.5111	Remote Similarity	NPC297987
0.5111	Remote Similarity	NPC168822
0.5111	Remote Similarity	NPC277205
0.5111	Remote Similarity	NPC37919
0.5111	Remote Similarity	NPC136042
0.5111	Remote Similarity	NPC323593
0.5111	Remote Similarity	NPC203500
0.5109	Remote Similarity	NPC168584
0.5109	Remote Similarity	NPC488071
0.5065	Remote Similarity	NPC306821
0.5056	Remote Similarity	NPC331652
0.5055	Remote Similarity	NPC24043
0.5055	Remote Similarity	NPC488080
0.5055	Remote Similarity	NPC472385
0.5055	Remote Similarity	NPC169977
0.5054	Remote Similarity	NPC21666

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC158034 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	5716
0.1-0.2	3351
0.2-0.3	68
0.3-0.4	11
0.4-0.5	4
0.5-0.6	0
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
		NPD

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