NPASS Compound

Natural Product: NPC103616

Natural Product ID	NPC103616
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	Parvispinoside B
IUPAC Name	n.a.
Synonyms	Parvispinoside B
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL447445
PubChem CID	11629532
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0001013] Steroidal glycosides [CHEMONTID:0002364] Steroidal saponins

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 178187 0 0 0 0 0 0 0 0999 V2000 -3.6138 1.6774 -3.3907 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.8931 1.3507 -2.8819 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.6738 0.8014 -1.5147 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.0592 1.6829 -0.6362 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.5139 0.8658 0.3890 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.4777 1.4948 1.0303 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.3016 0.8516 0.7720 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.3203 1.7016 -0.0104 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8657 2.1348 0.8145 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6906 0.9961 1.3093 C 0 0 1 0 0 0 0 0 0 0 0 0 0.7261 -0.1713 1.5707 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.6124 0.2893 2.0237 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4107 -1.1933 2.3974 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6227 -1.6846 1.6764 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4923 -0.6321 1.0667 C 0 0 2 0 0 0 0 0 0 0 0 0 2.6833 0.4486 0.3490 C 0 0 2 0 0 0 0 0 0 0 0 0 3.5511 1.4577 -0.3028 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5938 0.8297 -1.1890 C 0 0 0 0 0 0 0 0 0 0 0 0 5.3420 -0.2631 -0.5064 C 0 0 1 0 0 0 0 0 0 0 0 0 4.3445 -1.2656 0.0310 C 0 0 1 0 0 0 0 0 0 0 0 0 5.2593 -2.3589 0.4994 C 0 0 0 0 0 0 0 0 0 0 0 0 6.2988 -2.3909 -0.5964 C 0 0 1 0 0 0 0 0 0 0 0 0 6.0825 -1.1612 -1.4564 C 0 0 2 0 0 0 0 0 0 0 0 0 7.4467 -0.7323 -1.8293 C 0 0 2 0 0 0 0 0 0 0 0 0 7.6123 -0.9117 -3.3330 C 0 0 0 0 0 0 0 0 0 0 0 0 8.3484 -1.7395 -1.1577 C 0 0 1 0 0 0 0 0 0 0 0 0 7.6013 -2.2822 -0.1097 O 0 0 0 0 0 0 0 0 0 0 0 0 8.7425 -2.7686 -2.0087 O 0 0 0 0 0 0 0 0 0 0 0 0 9.5809 -1.1169 -0.5753 C 0 0 0 0 0 0 0 0 0 0 0 0 10.4167 -0.4237 -1.6266 C 0 0 0 0 0 0 0 0 0 0 0 0 11.6563 0.2154 -1.1152 C 0 0 2 0 0 0 0 0 0 0 0 0 12.6384 -0.7107 -0.4595 C 0 0 0 0 0 0 0 0 0 0 0 0 13.7234 0.0723 -0.0556 O 0 0 0 0 0 0 0 0 0 0 0 0 14.7110 -0.6569 0.5519 C 0 0 2 0 0 0 0 0 0 0 0 0 14.9604 -0.1387 1.8073 O 0 0 0 0 0 0 0 0 0 0 0 0 15.3873 1.1534 1.7364 C 0 0 2 0 0 0 0 0 0 0 0 0 14.4738 2.0726 2.5517 C 0 0 0 0 0 0 0 0 0 0 0 0 14.9131 3.3928 2.4738 O 0 0 0 0 0 0 0 0 0 0 0 0 15.5879 1.7440 0.3849 C 0 0 2 0 0 0 0 0 0 0 0 0 16.2614 0.8166 -0.5888 C 0 0 1 0 0 0 0 0 0 0 0 0 16.0149 -0.6371 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28 1 6 26 29 1 0 29 30 1 0 30 31 1 0 31 32 1 0 32 33 1 0 33 34 1 0 34 35 1 0 35 36 1 0 36 37 1 0 37 38 1 0 36 39 1 0 39 40 1 0 40 41 1 0 41 42 1 0 40 43 1 0 39 44 1 0 31 45 1 0 19 46 1 1 10 47 1 1 5 48 1 0 48 49 1 0 49 50 1 0 50 51 1 0 51 52 1 0 52 53 1 0 53 54 1 0 54 55 1 0 55 56 1 0 54 57 1 0 57 58 1 0 58 59 1 0 59 60 1 0 60 61 1 0 61 62 1 0 62 63 1 0 63 64 1 0 64 65 1 0 63 66 1 0 66 67 1 0 67 68 1 0 68 69 1 0 67 70 1 0 66 71 1 0 58 72 1 0 72 73 1 0 73 74 1 0 74 75 1 0 75 76 1 0 76 77 1 0 77 78 1 0 78 79 1 0 77 80 1 0 76 81 1 0 57 82 1 0 49 83 1 0 48 84 1 0 50 3 1 0 59 52 1 0 68 61 1 0 78 73 1 0 12 7 1 0 20 15 1 0 27 22 1 0 41 34 1 0 16 10 1 0 23 19 1 0 1 85 1 0 2 86 1 0 2 87 1 0 3 88 1 6 5 89 1 6 7 90 1 6 8 91 1 0 8 92 1 0 9 93 1 0 9 94 1 0 11 95 1 6 12 96 1 0 12 97 1 0 13 98 1 0 13 99 1 0 14100 1 0 14101 1 0 15102 1 1 16103 1 6 17104 1 0 17105 1 0 18106 1 0 18107 1 0 20108 1 6 21109 1 0 21110 1 0 22111 1 6 23112 1 6 24113 1 1 25114 1 0 25115 1 0 25116 1 0 28117 1 0 29118 1 0 29119 1 0 30120 1 0 30121 1 0 31122 1 6 32123 1 0 32124 1 0 34125 1 1 36126 1 1 37127 1 0 37128 1 0 38129 1 0 39130 1 6 40131 1 6 41132 1 6 42133 1 0 43134 1 0 44135 1 0 45136 1 0 45137 1 0 45138 1 0 46139 1 0 46140 1 0 46141 1 0 47142 1 0 47143 1 0 47144 1 0 48145 1 1 49146 1 6 50147 1 6 52148 1 6 54149 1 6 55150 1 0 55151 1 0 56152 1 0 57153 1 1 58154 1 6 59155 1 1 61156 1 6 63157 1 6 64158 1 0 64159 1 0 65160 1 0 66161 1 1 67162 1 6 68163 1 1 69164 1 0 70165 1 0 71166 1 0 73167 1 6 75168 1 0 75169 1 0 76170 1 1 77171 1 6 78172 1 1 79173 1 0 80174 1 0 81175 1 0 82176 1 0 83177 1 0 84178 1 0 M END

Standard InCHIKey	FJLUJBDSFBGOPL-AEORFYTQSA-N
Standard InCHI	InChI=1S/C56H94O28/c1-21(19-74-49-43(70)39(66)36(63)30(15-57)77-49)7-12-56(73)22(2)34-29(84-56)14-27-25-6-5-23-13-24(8-10-54(23,3)26(25)9-11-55(27,34)4)76-51-45(72)41(68)46(33(18-60)80-51)81-53-48(83-52-44(71)40(67)37(64)31(16-58)78-52)47(38(65)32(17-59)79-53)82-50-42(69)35(62)28(61)20-75-50/h21-53,57-73H,5-20H2,1-4H3/t21-,22+,23+,24+,25-,26+,27+,28-,29+,30-,31-,32-,33-,34+,35+,36-,37+,38-,39+,40+,41-,42-,43-,44-,45-,46+,47+,48-,49-,50+,51-,52+,53+,54+,55+,56-/m1/s1
SMILES	OC[C@H]1O[C@@H](O[C@H]2CC[C@]3([C@H](C2)CC[C@@H]2[C@@H]3CC[C@]3([C@H]2C[C@H]2[C@@H]3[C@H](C)[C@@](O2)(O)CC[C@H](CO[C@@H]2O[C@H](CO)[C@H]([C@@H]([C@H]2O)O)O)C)C)C)[C@@H]([C@H]([C@H]1O[C@@H]1O[C@H](CO)[C@H]([C@@H]([C@H]1O[C@@H]1O[C@H](CO)[C@@H]([C@@H]([C@H]1O)O)O)O[C@@H]1OC[C@H]([C@@H]([C@H]1O)O)O)O)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	1214.59	Volume:	1137.693 ? Van der Waals volume.
Dense:	1.068	LogP:	0.302 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	0.995 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-3.424 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	18.0	Rigid Bonds:	54.0
TPSA:	445.44 ? Topological Polar Surface Area.	H-Bond Acceptor:	28.0
H-Bond Donor:	17.0	Rings:	10.0
Heavy Atoms:	28.0

MedChem Properties

QED Drug-Likeness Score:	0.057	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	7.248	Fsp³:	1.0
MCE-18:	200.571 ? 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:	1
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.595	Fluc inhibitor:	0.0 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.002 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.0 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.449	Promiscuous compounds:	0.29

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-7.169	MDCK Permeability:	-5.058
Pgp-inhibitor:	0.0	Pgp-substrate:	0.997
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):	0.998
20% Bioavailability (F20%):	0.958	30% Bioavailability (F30%):	1.0
50% Bioavailability (F50%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.009
Plasma Protein Binding (PPB):	22.295%	Volume Distribution (VD):	-0.421
Fu:	51.185% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.002
BSEP inhibitor:	0.0

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	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:	0.82	CYP3A4-substrate:	0.999
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.032
HLM stability:	0.001 ? 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):

-0.702

Half-life (T1/2):

3.491

ADMET: Toxicity

hERG Blockers:	0.001	hERG Blockers (10um):	0.001
Human Hepatotoxicity (H-HT):	0.774	Drug-induced Liver Injury (DILI):	0.971
AMES Toxicity:	0.997	Rat Oral Acute Toxicity:	0.0
Maximum Recommended Daily Dose:	0.0	Skin Sensitization:	1.0
Carcinogencity:	0.033	Eye Corrosion:	0.0
Eye Irritation:	0.0	Respiratory Toxicity:	0.0
Drug-induced Neurotoxicity:	0.0	Ototoxicity:	1.0
Hematotoxicity:	0.959	Drug-induced Nephrotoxicity:	0.997
Genotoxicity:	0.003	RPMI-8226 Immunitoxicity:	0.299
A549 Cytotoxicity:	0.999	Hek293 Cytotoxicity:	0.971
BCF:	1.311 ? 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:	3.327 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.462 ? 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
NPO33193	tribulus parvispinus	Species	n.a.	Eukaryota	n.a.	n.a.	n.a.	PMID[16252924]

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
IC50	3
Activity	2

Activity Type	# Activity
Cell line	5

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
NPT65	Cell line	HepG2	Homo sapiens	IC50	>	100000.0	nM	PMID[17253840]
NPT83	Cell line	MCF7	Homo sapiens	IC50	=	94000.0	nM	PMID[21182258]
NPT466	Cell line	U-937	Homo sapiens	IC50	=	500.0	nM	PMID[17253840]
NPT466	Cell line	U-937	Homo sapiens	Activity	=	27.0	%	PMID[7714533]
NPT466	Cell line	U-937	Homo sapiens	Activity	=	26.0	%	PMID[16203143]

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 NPC103616 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	29277
0.1-0.2	17631
0.2-0.3	2353
0.3-0.4	425
0.4-0.5	73
0.5-0.6	53
0.6-0.7	21
0.7-0.8	0
0.8-0.85	2
0.85-0.9	2
0.9-0.95	3
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC98018
1.0	High Similarity	NPC284104
0.9286	High Similarity	NPC84111
0.9286	High Similarity	NPC287483
0.9286	High Similarity	NPC470865
0.8776	High Similarity	NPC470863
0.8529	High Similarity	NPC92297
0.8485	Intermediate Similarity	NPC51520
0.8485	Intermediate Similarity	NPC303069
0.7982	Intermediate Similarity	NPC273002
0.7619	Intermediate Similarity	NPC116756
0.75	Intermediate Similarity	NPC97700
0.75	Intermediate Similarity	NPC30856
0.7453	Intermediate Similarity	NPC470861
0.7156	Intermediate Similarity	NPC218571
0.7156	Intermediate Similarity	NPC487615
0.7143	Intermediate Similarity	NPC470866
0.7113	Intermediate Similarity	NPC291203
0.7113	Intermediate Similarity	NPC217205
0.7027	Intermediate Similarity	NPC132080
0.6991	Remote Similarity	NPC262050
0.6762	Remote Similarity	NPC475351
0.6757	Remote Similarity	NPC232037
0.6697	Remote Similarity	NPC102016
0.6697	Remote Similarity	NPC95051
0.6696	Remote Similarity	NPC470864
0.6579	Remote Similarity	NPC233433
0.646	Remote Similarity	NPC232611
0.6429	Remote Similarity	NPC485600
0.6396	Remote Similarity	NPC184617
0.6339	Remote Similarity	NPC115165
0.6261	Remote Similarity	NPC249265
0.6216	Remote Similarity	NPC51172
0.6216	Remote Similarity	NPC49032
0.6198	Remote Similarity	NPC220836
0.6176	Remote Similarity	NPC485602
0.6154	Remote Similarity	NPC250393
0.6095	Remote Similarity	NPC206003
0.6095	Remote Similarity	NPC473610
0.6087	Remote Similarity	NPC475625
0.6075	Remote Similarity	NPC485601
0.595	Remote Similarity	NPC94086
0.595	Remote Similarity	NPC473817
0.5932	Remote Similarity	NPC476112
0.5932	Remote Similarity	NPC307534
0.5913	Remote Similarity	NPC475319
0.5865	Remote Similarity	NPC325828
0.5862	Remote Similarity	NPC247037
0.5826	Remote Similarity	NPC73243
0.5826	Remote Similarity	NPC244086
0.5826	Remote Similarity	NPC84956
0.5812	Remote Similarity	NPC473518
0.5804	Remote Similarity	NPC473601
0.5798	Remote Similarity	NPC23808
0.5798	Remote Similarity	NPC87998
0.578	Remote Similarity	NPC107962
0.5667	Remote Similarity	NPC470862
0.5586	Remote Similarity	NPC125324
0.5583	Remote Similarity	NPC92710
0.5574	Remote Similarity	NPC31896
0.5537	Remote Similarity	NPC83137
0.5526	Remote Similarity	NPC98696
0.552	Remote Similarity	NPC248202
0.547	Remote Similarity	NPC128572
0.5455	Remote Similarity	NPC108072
0.5385	Remote Similarity	NPC263359
0.5351	Remote Similarity	NPC485599
0.5349	Remote Similarity	NPC208832
0.5339	Remote Similarity	NPC151134
0.5315	Remote Similarity	NPC107188
0.5315	Remote Similarity	NPC476538
0.5315	Remote Similarity	NPC476539
0.529	Remote Similarity	NPC481189
0.5271	Remote Similarity	NPC210569
0.5246	Remote Similarity	NPC197003
0.5242	Remote Similarity	NPC256983
0.5234	Remote Similarity	NPC473505
0.5225	Remote Similarity	NPC128123
0.5225	Remote Similarity	NPC476540
0.5225	Remote Similarity	NPC476541
0.5214	Remote Similarity	NPC475643
0.5182	Remote Similarity	NPC329807
0.5175	Remote Similarity	NPC6295
0.5143	Remote Similarity	NPC329727
0.5126	Remote Similarity	NPC471464
0.512	Remote Similarity	NPC477811
0.5118	Remote Similarity	NPC470867
0.5086	Remote Similarity	NPC160426
0.5074	Remote Similarity	NPC330026
0.5042	Remote Similarity	NPC92890
0.5041	Remote Similarity	NPC309278
0.5038	Remote Similarity	NPC305771
0.5038	Remote Similarity	NPC94072
0.5038	Remote Similarity	NPC169816

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC103616 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	7992
0.1-0.2	1090
0.2-0.3	60
0.3-0.4	5
0.4-0.5	1
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
0.5865	Remote Similarity	NPD8171	Phase 2
0.5043	Remote Similarity	NPD8170	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