NPASS Compound

Natural Product: NPC555893

Natural Product ID	NPC555893
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	(1~{S},3~{R},5~{S},7~{R},9~{R},10~{R},12~{R},14~{R},15~{S},18~{R},19~{R},22~{S},23~{R})-10,22-dihydroxy-7,18-dimethyl-19-(5-oxo-2~{H}-furan-3-yl)spiro[4,6,11-trioxahexacyclo[12.11.0.0^{3,12}.0^{5,10}.0^{15,23}.0^{18,22}]pentacosane-9,2'-5~{H}-thiazole]-14-carbaldehyde
IUPAC Name	(1~{S},3~{R},5~{S},7~{R},9~{R},10~{R},12~{R},14~{R},15~{S},18~{R},19~{R},22~{S},23~{R})-10,22-dihydroxy-7,18-dimethyl-19-(5-oxo-2~{H}-furan-3-yl)spiro[4,6,11-trioxahexacyclo[12.11.0.0^{3,12}.0^{5,10}.0^{15,23}.0^{18,22}]pentacosane-9,2'-5~{H}-thiazole]-14-carbaldehyde
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
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 82 89 0 0 0 0 0 0 0 0999 V2000 -6.7164 0.4877 2.7837 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.3267 -0.0044 1.4052 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.7612 -1.3961 1.5554 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.3194 -1.8712 0.1948 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.8983 -3.2015 0.1801 N 0 0 0 0 0 0 0 0 0 0 0 0 -5.3515 -4.0219 -0.6064 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.3825 -3.5883 -1.5763 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.8319 -1.9792 -0.8507 S 0 0 0 0 0 0 0 0 0 0 0 0 -4.3734 -0.9098 -0.4832 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.4015 -1.2418 -1.8580 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.0722 -1.0562 -0.0693 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.3073 -0.0416 -0.6522 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8702 -0.2788 -0.4404 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0039 0.9611 -0.5437 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.0624 1.5158 -1.9293 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7200 1.0232 -2.8288 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.5950 1.9847 0.3689 C 0 0 1 0 0 0 0 0 0 0 0 0 0.3202 3.1504 0.6385 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5492 2.5726 1.3084 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2395 1.7206 0.2430 C 0 0 2 0 0 0 0 0 0 0 0 0 1.4152 0.5703 -0.2106 C 0 0 2 0 0 0 0 0 0 0 0 0 2.0813 -0.0187 -1.4505 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4453 0.5816 -1.6963 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3033 0.6079 -0.4779 C 0 0 2 0 0 0 0 0 0 0 0 0 5.6047 1.3074 -0.7800 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4878 -0.7549 0.1393 C 0 0 1 0 0 0 0 0 0 0 0 0 5.5301 -1.5918 -0.4280 C 0 0 0 0 0 0 0 0 0 0 0 0 6.2769 -1.4903 -1.4980 C 0 0 0 0 0 0 0 0 0 0 0 0 7.1903 -2.6296 -1.6083 C 0 0 0 0 0 0 0 0 0 0 0 0 8.0317 -2.8196 -2.5252 O 0 0 0 0 0 0 0 0 0 0 0 0 6.9518 -3.4367 -0.5318 O 0 0 0 0 0 0 0 0 0 0 0 0 5.9459 -2.8762 0.2467 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9335 -0.3597 1.5642 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7547 0.5701 1.9002 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6223 1.3723 0.6649 C 0 0 2 0 0 0 0 0 0 0 0 0 4.2743 2.5973 0.9180 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.9259 2.4073 -0.2165 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8480 1.2493 -0.1435 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.0669 1.4656 -0.8038 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.9304 0.4655 -0.3560 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.2925 0.8078 0.9462 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.7875 0.7575 3.3567 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.2806 -0.3199 3.2855 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.3440 1.4101 2.7117 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.1891 0.0160 0.7251 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.5805 -2.0534 1.8928 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.9747 -1.3928 2.3084 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.0188 -5.0902 -0.6242 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.2531 -4.2719 -1.6072 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.9686 -3.3839 -2.5844 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.8024 -2.0455 -1.9723 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.5173 -0.1121 -1.7548 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.7121 -0.6925 0.5750 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.5203 -1.0749 -1.1445 H 0 0 0 0 0 0 0 0 0 0 0 0 0.5081 2.4070 -2.1609 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.8059 1.4816 1.3427 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.1982 3.8300 1.3219 H 0 0 0 0 0 0 0 0 0 0 0 0 0.6207 3.5899 -0.3209 H 0 0 0 0 0 0 0 0 0 0 0 0 1.3124 1.9959 2.2089 H 0 0 0 0 0 0 0 0 0 0 0 0 2.2411 3.4267 1.4943 H 0 0 0 0 0 0 0 0 0 0 0 0 2.3404 2.4168 -0.6422 H 0 0 0 0 0 0 0 0 0 0 0 0 1.3460 -0.2529 0.5270 H 0 0 0 0 0 0 0 0 0 0 0 0 2.1907 -1.1005 -1.3916 H 0 0 0 0 0 0 0 0 0 0 0 0 1.4541 0.2330 -2.3299 H 0 0 0 0 0 0 0 0 0 0 0 0 3.9449 -0.0876 -2.4390 H 0 0 0 0 0 0 0 0 0 0 0 0 3.3978 1.5725 -2.1678 H 0 0 0 0 0 0 0 0 0 0 0 0 6.4877 0.7551 -0.3816 H 0 0 0 0 0 0 0 0 0 0 0 0 5.6869 2.3172 -0.2916 H 0 0 0 0 0 0 0 0 0 0 0 0 5.7136 1.5596 -1.8749 H 0 0 0 0 0 0 0 0 0 0 0 0 3.5041 -1.2397 0.2316 H 0 0 0 0 0 0 0 0 0 0 0 0 6.2496 -0.7074 -2.2194 H 0 0 0 0 0 0 0 0 0 0 0 0 6.2172 -2.7204 1.2905 H 0 0 0 0 0 0 0 0 0 0 0 0 5.0523 -3.5573 0.1777 H 0 0 0 0 0 0 0 0 0 0 0 0 4.9836 -1.2204 2.2275 H 0 0 0 0 0 0 0 0 0 0 0 0 5.8352 0.2602 1.5076 H 0 0 0 0 0 0 0 0 0 0 0 0 2.9094 -0.1040 2.1213 H 0 0 0 0 0 0 0 0 0 0 0 0 3.9668 1.1552 2.8039 H 0 0 0 0 0 0 0 0 0 0 0 0 4.2375 2.8010 1.9028 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.8213 2.7843 -1.2533 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.3195 3.2084 0.4566 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.1255 1.1068 0.9423 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.8811 0.4922 -0.9656 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 2 0 6 7 1 0 7 8 1 0 4 9 1 0 9 10 1 6 9 11 1 0 11 12 1 0 12 13 1 0 13 14 1 0 14 15 1 6 15 16 2 0 14 17 1 0 17 18 1 0 18 19 1 0 19 20 1 0 20 21 1 0 21 22 1 0 22 23 1 0 23 24 1 0 24 25 1 6 24 26 1 0 26 27 1 0 27 28 2 0 28 29 1 0 29 30 2 0 29 31 1 0 31 32 1 0 26 33 1 0 33 34 1 0 34 35 1 0 35 36 1 1 17 37 1 0 37 38 1 0 38 39 1 0 39 40 1 0 40 41 1 0 41 2 1 0 4 8 1 6 40 9 1 0 38 12 1 0 21 14 1 0 35 24 1 0 35 20 1 0 32 27 1 0 1 42 1 0 1 43 1 0 1 44 1 0 2 45 1 6 3 46 1 0 3 47 1 0 6 48 1 0 7 49 1 0 7 50 1 0 10 51 1 0 12 52 1 6 13 53 1 0 13 54 1 0 15 55 1 0 17 56 1 1 18 57 1 0 18 58 1 0 19 59 1 0 19 60 1 0 20 61 1 6 21 62 1 1 22 63 1 0 22 64 1 0 23 65 1 0 23 66 1 0 25 67 1 0 25 68 1 0 25 69 1 0 26 70 1 1 28 71 1 0 32 72 1 0 32 73 1 0 33 74 1 0 33 75 1 0 34 76 1 0 34 77 1 0 36 78 1 0 37 79 1 0 37 80 1 0 38 81 1 1 40 82 1 6 M END

Standard InCHIKey	DONIPVCAKBPJLH-DMSJIHDJSA-N
Standard InCHI	InChI=1S/C31H41NO8S/c1-17-13-30(32-9-10-41-30)31(36)26(38-17)39-23-12-19-3-4-22-21(28(19,16-33)14-24(23)40-31)5-7-27(2)20(6-8-29(22,27)35)18-11-25(34)37-15-18/h9,11,16-17,19-24,26,35-36H,3-8,10,12-15H2,1-2H3/t17-,19+,20-,21+,22-,23-,24-,26+,27-,28-,29+,30-,31-/m1/s1
SMILES	C[C@@H]1C[C@]2(N=CCS2)[C@]2(O)O[C@@H]3C[C@@]4(C=O)[C@@H](CC[C@@H]5[C@@H]4CC[C@]4(C)[C@@H](C6=CC(=O)OC6)CC[C@]54O)C[C@H]3O[C@@H]2O1

Calculated Properties

Physi-Chem Properties

Molecular Weight:	587.26	Volume:	565.562 ? Van der Waals volume.
Dense:	1.038	LogP:	1.417 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	2.007 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-3.549 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	2.0	Rigid Bonds:	42.0
TPSA:	123.88 ? Topological Polar Surface Area.	H-Bond Acceptor:	9.0
H-Bond Donor:	2.0	Rings:	8.0
Heavy Atoms:	10.0

MedChem Properties

QED Drug-Likeness Score:	0.285	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	6.429	Fsp³:	0.839
MCE-18:	188.263 ? MCE-18 stands for medicinal chemistry evolution.MCE-18≥45 is considered a suitable value.	Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Rejected	GSK Rule:	Accepted
Golden Triangle Rule:	Accepted	BMS Rule:	1
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.629	Fluc inhibitor:	0.001 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.005 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.003 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.079	Promiscuous compounds:	0.3

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.292	MDCK Permeability:	-4.835
Pgp-inhibitor:	0.186	Pgp-substrate:	0.647
PAMPA:	0.48 ? 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):	0.002
20% Bioavailability (F20%):	0.682	30% Bioavailability (F30%):	0.623
50% Bioavailability (F50%):	0.986

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.117	MRP1:	0.512
Plasma Protein Binding (PPB):	94.118%	Volume Distribution (VD):	0.381
Fu:	4.393% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.99
OATP1B3 inhibitor:	0.967	BCRP inhibitor:	0.017
BSEP inhibitor:	0.993

ADMET: Metabolism

CYP1A2-inhibitor:	0.076	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.095	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.077	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.002
CYP3A4-inhibitor:	0.997	CYP3A4-substrate:	0.013
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.016
HLM stability:	0.346 ? 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):

2.579

Half-life (T1/2):

2.708

ADMET: Toxicity

hERG Blockers:	0.051	hERG Blockers (10um):	0.36
Human Hepatotoxicity (H-HT):	0.757	Drug-induced Liver Injury (DILI):	0.755
AMES Toxicity:	0.997	Rat Oral Acute Toxicity:	0.996
Maximum Recommended Daily Dose:	1.0	Skin Sensitization:	1.0
Carcinogencity:	0.991	Eye Corrosion:	0.0
Eye Irritation:	0.0	Respiratory Toxicity:	0.972
Drug-induced Neurotoxicity:	0.049	Ototoxicity:	0.399
Hematotoxicity:	0.945	Drug-induced Nephrotoxicity:	0.992
Genotoxicity:	1.0	RPMI-8226 Immunitoxicity:	0.856
A549 Cytotoxicity:	0.51	Hek293 Cytotoxicity:	0.996
BCF:	0.628 ? 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:	3.618 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.29 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.651 ? 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
NPO46925	Asclepias curassavica L.	Genus	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO63778	Asclepias fruticosa R.Br.	Genus	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]

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 NPC555893 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	16267
0.1-0.2	31883
0.2-0.3	1473
0.3-0.4	102
0.4-0.5	94
0.5-0.6	21
0.6-0.7	9
0.7-0.8	1
0.8-0.85	2
0.85-0.9	0
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC163365
0.8353	Intermediate Similarity	NPC85369
0.8313	Intermediate Similarity	NPC33934
0.7294	Intermediate Similarity	NPC253456
0.7294	Intermediate Similarity	NPC159338
0.7294	Intermediate Similarity	NPC171619
0.7241	Intermediate Similarity	NPC91
0.6818	Remote Similarity	NPC277374
0.6774	Remote Similarity	NPC480905
0.6667	Remote Similarity	NPC488161
0.6667	Remote Similarity	NPC16569
0.6596	Remote Similarity	NPC470094
0.6526	Remote Similarity	NPC473040
0.6495	Remote Similarity	NPC476221
0.6495	Remote Similarity	NPC477709
0.6044	Remote Similarity	NPC104585
0.5957	Remote Similarity	NPC488162
0.5957	Remote Similarity	NPC298783
0.5957	Remote Similarity	NPC93416
0.5938	Remote Similarity	NPC142756
0.5895	Remote Similarity	NPC157817
0.5851	Remote Similarity	NPC42670
0.5851	Remote Similarity	NPC19124
0.5625	Remote Similarity	NPC329905
0.54	Remote Similarity	NPC225385
0.5354	Remote Similarity	NPC488158
0.5354	Remote Similarity	NPC488159
0.5306	Remote Similarity	NPC609258
0.5294	Remote Similarity	NPC196931
0.5258	Remote Similarity	NPC488160
0.5155	Remote Similarity	NPC88668
0.5155	Remote Similarity	NPC250556
0.5104	Remote Similarity	NPC469750
0.5104	Remote Similarity	NPC480915
0.51	Remote Similarity	NPC474466
0.5098	Remote Similarity	NPC488163
0.5052	Remote Similarity	NPC480914

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC555893 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	6158
0.1-0.2	2940
0.2-0.3	38
0.3-0.4	8
0.4-0.5	4
0.5-0.6	1
0.6-0.7	0
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
0.7065	Intermediate Similarity	NPD7625	Phase 1
0.5155	Remote Similarity	NPD7507	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