NPASS Compound

Natural Product: NPC605067

Natural Product ID	NPC605067
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	GLTCTFBPNQJRQT-FZFRBNDOSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL487212
PubChem CID	n.a.
Chemical Classification	CHEMONTID:0000000 [Organic compounds]

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 6.1520 3.6386 0.2084 C 0 0 0 0 0 0 0 0 0 0 0 0 6.8889 2.4339 -0.0126 O 0 0 0 0 0 0 0 0 0 0 0 0 6.1543 1.2633 -0.1687 C 0 0 0 0 0 0 0 0 0 0 0 0 4.7812 1.2328 -0.1172 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0384 0.0816 -0.2699 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7323 0.0811 -0.2164 O 0 0 0 0 0 0 0 0 0 0 0 0 1.9770 -0.9753 -0.3535 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5085 -0.8801 -0.2781 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0496 0.3686 -0.0560 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4116 0.5070 0.0218 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3027 -0.5765 -0.1147 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6294 -0.3038 -0.0168 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.7797 -1.0381 -0.0881 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.6404 -0.6577 -1.1167 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.2418 0.5472 -0.9486 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.3420 1.7215 -1.3448 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.9657 1.6518 -2.6711 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.8244 0.8195 0.3908 C 0 0 1 0 0 0 0 0 0 0 0 0 -8.0805 0.2312 0.5461 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.9495 0.3567 1.5327 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.8579 1.2002 1.6213 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.5453 -1.0585 1.2512 C 0 0 1 0 0 0 0 0 0 0 0 0 -6.6883 -1.8237 1.0278 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7090 -1.7958 -0.3335 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5257 -2.9134 -0.4784 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.3155 -1.9573 -0.4162 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6017 -2.1847 -0.5715 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9967 -2.2635 -0.6413 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5596 -3.3680 -0.8400 O 0 0 0 0 0 0 0 0 0 0 0 0 4.7360 -1.1124 -0.4885 C 0 0 0 0 0 0 0 0 0 0 0 0 6.1177 -1.1107 -0.5449 C 0 0 0 0 0 0 0 0 0 0 0 0 6.7916 -2.3051 -0.7626 O 0 0 0 0 0 0 0 0 0 0 0 0 6.8367 0.0619 -0.3878 C 0 0 0 0 0 0 0 0 0 0 0 0 8.2144 0.0718 -0.4428 O 0 0 0 0 0 0 0 0 0 0 0 0 9.0472 -0.1056 0.6737 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9093 4.4475 0.3054 H 0 0 0 0 0 0 0 0 0 0 0 0 5.5993 3.5124 1.1507 H 0 0 0 0 0 0 0 0 0 0 0 0 5.4864 3.8205 -0.6692 H 0 0 0 0 0 0 0 0 0 0 0 0 4.2562 2.1563 0.0510 H 0 0 0 0 0 0 0 0 0 0 0 0 0.5707 1.2453 0.0586 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.8721 1.4826 0.1964 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.5682 -2.1050 -0.2728 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.0937 0.5935 -1.6917 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.8883 2.6758 -1.1936 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.4580 1.7879 -0.6481 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.8489 2.5746 -3.0106 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.9692 1.9174 0.5015 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.4953 0.5317 1.3889 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.5872 0.4072 2.4542 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.2000 2.0815 1.9573 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.8802 -1.5002 2.0039 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.4243 -2.7795 0.8582 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.1669 -3.7936 -0.1464 H 0 0 0 0 0 0 0 0 0 0 0 0 0.0644 -2.9439 -0.5891 H 0 0 0 0 0 0 0 0 0 0 0 0 2.0700 -3.0950 -0.6944 H 0 0 0 0 0 0 0 0 0 0 0 0 7.4255 -2.3942 -1.5406 H 0 0 0 0 0 0 0 0 0 0 0 0 8.4389 -0.3661 1.5632 H 0 0 0 0 0 0 0 0 0 0 0 0 9.5941 0.8347 0.8895 H 0 0 0 0 0 0 0 0 0 0 0 0 9.7623 -0.9303 0.4287 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 2 0 9 10 1 0 10 11 2 0 11 12 1 0 12 13 1 0 13 14 1 0 14 15 1 0 15 16 1 0 16 17 1 0 15 18 1 0 18 19 1 0 18 20 1 0 20 21 1 0 20 22 1 0 22 23 1 0 11 24 1 0 24 25 1 0 24 26 2 0 7 27 2 0 27 28 1 0 28 29 2 0 28 30 1 0 30 31 1 0 31 32 1 0 31 33 2 0 33 34 1 0 34 35 1 0 33 3 1 0 30 5 2 0 26 8 1 0 22 13 1 0 1 36 1 0 1 37 1 0 1 38 1 0 4 39 1 0 9 40 1 0 10 41 1 0 13 42 1 6 15 43 1 6 16 44 1 0 16 45 1 0 17 46 1 0 18 47 1 1 19 48 1 0 20 49 1 1 21 50 1 0 22 51 1 1 23 52 1 0 25 53 1 0 26 54 1 0 27 55 1 0 32 56 1 0 35 57 1 0 35 58 1 0 35 59 1 0 M END

Standard InCHIKey	GLTCTFBPNQJRQT-FZFRBNDOSA-N
Standard InCHI	InChI=1S/C23H24O12/c1-31-15-7-14-17(19(28)22(15)32-2)11(26)6-13(33-14)9-3-4-12(10(25)5-9)34-23-21(30)20(29)18(27)16(8-24)35-23/h3-7,16,18,20-21,23-25,27-30H,8H2,1-2H3/t16-,18-,20+,21-,23-/m1/s1
SMILES	COc1cc2oc(-c3ccc(O[C@@H]4O[C@H](CO)[C@@H](O)[C@H](O)[C@H]4O)c(O)c3)cc(=O)c2c(O)c1OC

Calculated Properties

Physi-Chem Properties

Molecular Weight:	492.13	Volume:	456.529 ? Van der Waals volume.
Dense:	1.078	LogP:	1.221 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	1.584 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-3.379 ? 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:	3.971	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:	0.571	Fluc inhibitor:	0.301 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.95 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.911 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.092	Promiscuous compounds:	0.681

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-6.129	MDCK Permeability:	-5.379
Pgp-inhibitor:	0.003	Pgp-substrate:	0.274
PAMPA:	0.916 ? 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):	0.619
20% Bioavailability (F20%):	0.229	30% Bioavailability (F30%):	0.975
50% Bioavailability (F50%):	0.995

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.004	MRP1:	0.543
Plasma Protein Binding (PPB):	83.57%	Volume Distribution (VD):	-0.096
Fu:	14.501% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.774
BSEP inhibitor:	0.012

ADMET: Metabolism

CYP1A2-inhibitor:	0.003	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.004	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.014
CYP3A4-inhibitor:	0.0	CYP3A4-substrate:	0.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.602
HLM stability:	0.029 ? 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):

2.911

Half-life (T1/2):

3.388

ADMET: Toxicity

hERG Blockers:	0.021	hERG Blockers (10um):	0.107
Human Hepatotoxicity (H-HT):	0.578	Drug-induced Liver Injury (DILI):	0.925
AMES Toxicity:	0.838	Rat Oral Acute Toxicity:	0.047
Maximum Recommended Daily Dose:	0.074	Skin Sensitization:	0.988
Carcinogencity:	0.34	Eye Corrosion:	0.0
Eye Irritation:	0.565	Respiratory Toxicity:	0.046
Drug-induced Neurotoxicity:	0.004	Ototoxicity:	0.808
Hematotoxicity:	0.261	Drug-induced Nephrotoxicity:	0.37
Genotoxicity:	0.705	RPMI-8226 Immunitoxicity:	0.128
A549 Cytotoxicity:	0.304	Hek293 Cytotoxicity:	0.336
BCF:	0.403 ? 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:	3.004 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.428 ? 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
NPO1765	Cirsium lineare	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO1765	Cirsium lineare	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO1765	Cirsium lineare	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO1765	Cirsium lineare	Species	Asteraceae	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
Individual protein	1

Molecular-level activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1310	Individual protein	Xanthine dehydrogenase	Bos taurus	Inhibition	=	0.0	%	PMID[3379415]

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 NPC605067 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	21416
0.1-0.2	24365
0.2-0.3	2703
0.3-0.4	948
0.4-0.5	301
0.5-0.6	71
0.6-0.7	35
0.7-0.8	0
0.8-0.85	4
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.8472	Intermediate Similarity	NPC58053
0.8026	Intermediate Similarity	NPC609451
0.8	Intermediate Similarity	NPC186807
0.8	Intermediate Similarity	NPC45638
0.7895	Intermediate Similarity	NPC201292
0.7692	Intermediate Similarity	NPC22832
0.7632	Intermediate Similarity	NPC93337
0.7595	Intermediate Similarity	NPC602805
0.7532	Intermediate Similarity	NPC105025
0.7342	Intermediate Similarity	NPC191306
0.725	Intermediate Similarity	NPC21666
0.6857	Remote Similarity	NPC160951
0.675	Remote Similarity	NPC95090
0.675	Remote Similarity	NPC27408
0.6667	Remote Similarity	NPC58716
0.6627	Remote Similarity	NPC243930
0.6627	Remote Similarity	NPC486578
0.6548	Remote Similarity	NPC607707
0.642	Remote Similarity	NPC45618
0.6353	Remote Similarity	NPC311830
0.6341	Remote Similarity	NPC146792
0.6341	Remote Similarity	NPC189142
0.6341	Remote Similarity	NPC77660
0.6322	Remote Similarity	NPC254540
0.631	Remote Similarity	NPC285197
0.6265	Remote Similarity	NPC24043
0.6237	Remote Similarity	NPC256760
0.6235	Remote Similarity	NPC284960
0.6235	Remote Similarity	NPC601144
0.6235	Remote Similarity	NPC609478
0.622	Remote Similarity	NPC143851
0.6207	Remote Similarity	NPC211594
0.619	Remote Similarity	NPC117260
0.6163	Remote Similarity	NPC88023
0.6163	Remote Similarity	NPC307518
0.6163	Remote Similarity	NPC309025
0.6145	Remote Similarity	NPC168822
0.6118	Remote Similarity	NPC488071
0.6092	Remote Similarity	NPC488072
0.6071	Remote Similarity	NPC603655
0.6024	Remote Similarity	NPC261866
0.6024	Remote Similarity	NPC39360
0.6024	Remote Similarity	NPC29763
0.6024	Remote Similarity	NPC210003
0.6023	Remote Similarity	NPC172807
0.6	Remote Similarity	NPC21100
0.5955	Remote Similarity	NPC251417
0.593	Remote Similarity	NPC60735
0.593	Remote Similarity	NPC26230
0.587	Remote Similarity	NPC204693
0.5862	Remote Similarity	NPC120099
0.5862	Remote Similarity	NPC601710
0.5851	Remote Similarity	NPC483707
0.5814	Remote Similarity	NPC182045
0.5753	Remote Similarity	NPC145379
0.5747	Remote Similarity	NPC224462
0.5698	Remote Similarity	NPC610763
0.5684	Remote Similarity	NPC209296
0.5676	Remote Similarity	NPC25270
0.5647	Remote Similarity	NPC289667
0.5647	Remote Similarity	NPC110349
0.56	Remote Similarity	NPC69394
0.5591	Remote Similarity	NPC3583
0.5591	Remote Similarity	NPC607513
0.5556	Remote Similarity	NPC48773
0.5543	Remote Similarity	NPC603300
0.5517	Remote Similarity	NPC181712
0.5506	Remote Similarity	NPC229729
0.5455	Remote Similarity	NPC222936
0.5455	Remote Similarity	NPC205076
0.5455	Remote Similarity	NPC47781
0.5405	Remote Similarity	NPC239128
0.5402	Remote Similarity	NPC259152
0.5385	Remote Similarity	NPC469931
0.5385	Remote Similarity	NPC601586
0.5377	Remote Similarity	NPC198199
0.5361	Remote Similarity	NPC150767
0.5341	Remote Similarity	NPC245014
0.5341	Remote Similarity	NPC84362
0.5341	Remote Similarity	NPC27640
0.5333	Remote Similarity	NPC120163
0.5333	Remote Similarity	NPC276409
0.5287	Remote Similarity	NPC254306
0.5287	Remote Similarity	NPC19709
0.5287	Remote Similarity	NPC83283
0.5281	Remote Similarity	NPC42773
0.5281	Remote Similarity	NPC472459
0.5281	Remote Similarity	NPC45522
0.527	Remote Similarity	NPC75279
0.5269	Remote Similarity	NPC8856
0.5269	Remote Similarity	NPC473682
0.5263	Remote Similarity	NPC256283
0.5229	Remote Similarity	NPC120952
0.5227	Remote Similarity	NPC64305
0.5222	Remote Similarity	NPC611303
0.5204	Remote Similarity	NPC124155
0.5195	Remote Similarity	NPC212678
0.5169	Remote Similarity	NPC84265
0.5169	Remote Similarity	NPC488080
0.5169	Remote Similarity	NPC169977
0.5165	Remote Similarity	NPC101026
0.5165	Remote Similarity	NPC488077
0.5128	Remote Similarity	NPC25495
0.5128	Remote Similarity	NPC93376
0.5128	Remote Similarity	NPC223579
0.5114	Remote Similarity	NPC210042
0.5111	Remote Similarity	NPC27942
0.51	Remote Similarity	NPC475382
0.5063	Remote Similarity	NPC25292
0.5056	Remote Similarity	NPC297987
0.5056	Remote Similarity	NPC277205
0.5056	Remote Similarity	NPC37919
0.5056	Remote Similarity	NPC136042
0.5054	Remote Similarity	NPC203050
0.5054	Remote Similarity	NPC225434
0.5054	Remote Similarity	NPC190003
0.5046	Remote Similarity	NPC470719

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC605067 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	5164
0.1-0.2	3893
0.2-0.3	75
0.3-0.4	11
0.4-0.5	5
0.5-0.6	2
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
0.5684	Remote Similarity	NPD7054	Phase 4
0.5049	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