NPASS Compound

Natural Product: NPC483848

Natural Product ID	NPC483848
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	RVDLUHBVRBFQRM-JUHDBQHNSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	134152829
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 83 86 0 0 0 0 0 0 0 0999 V2000 -2.1623 -2.2010 2.6304 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8067 -1.3000 1.6308 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.5056 -2.0327 0.5105 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3622 -1.3435 -0.8187 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9370 -1.0901 -1.2046 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.0490 -0.6420 -0.0524 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.2388 -1.8634 0.3362 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5113 -2.2317 -0.8315 O 0 0 0 0 0 0 0 0 0 0 0 0 1.3395 -3.3276 -0.7341 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4134 -3.9560 0.3354 O 0 0 0 0 0 0 0 0 0 0 0 0 2.1359 -3.7524 -1.8958 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0654 0.4182 -0.4431 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.3221 1.8000 0.1094 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.0284 1.8492 1.4181 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.1140 0.4748 2.1000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.9599 -0.2074 1.0770 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.8194 0.7726 0.6080 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5318 1.9859 1.1545 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8186 3.0237 0.0907 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2814 2.3450 2.3943 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7729 0.6531 3.3367 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.1987 0.3181 4.5445 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0302 -0.1676 4.5279 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.8900 0.5030 5.8482 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9266 2.4772 0.1043 O 0 0 0 0 0 0 0 0 0 0 0 0 1.2147 3.6164 -0.6179 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2651 4.0476 -1.3076 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5449 4.2617 -0.5675 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6423 5.3553 -1.3684 O 0 0 0 0 0 0 0 0 0 0 0 0 2.4733 5.1304 -2.7014 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2764 0.0259 -0.4180 O 0 0 0 0 0 0 0 0 0 0 0 0 2.1372 -0.1223 -1.4615 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7207 0.1091 -2.5868 O 0 0 0 0 0 0 0 0 0 0 0 0 3.5180 -0.5424 -1.2802 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0493 -0.8182 -0.0153 C 0 0 0 0 0 0 0 0 0 0 0 0 5.3572 -1.2157 0.1370 C 0 0 0 0 0 0 0 0 0 0 0 0 6.1668 -1.3492 -0.9541 C 0 0 0 0 0 0 0 0 0 0 0 0 5.6646 -1.0832 -2.2034 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3541 -0.6860 -2.3459 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4561 -2.2104 -1.8857 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.0747 -2.1484 -3.1994 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1719 -1.0334 -3.7762 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.5659 -3.3425 -3.9266 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3645 -3.2726 2.3281 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0995 -2.0225 2.8197 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.6442 -2.1481 3.6546 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.6418 -0.7731 2.1910 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.6214 -2.1117 0.6831 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.1906 -3.0962 0.4108 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.7770 -2.0725 -1.5780 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.0326 -0.4636 -0.9394 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.9271 -0.2190 -1.9214 H 0 0 0 0 0 0 0 0 0 0 0 0 0.5246 -1.6338 1.1011 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.8335 -2.7489 0.5626 H 0 0 0 0 0 0 0 0 0 0 0 0 2.1219 -2.9887 -2.7098 H 0 0 0 0 0 0 0 0 0 0 0 0 3.2113 -3.9107 -1.6061 H 0 0 0 0 0 0 0 0 0 0 0 0 1.7569 -4.7215 -2.2761 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.2157 0.5476 -1.5516 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.9291 2.4214 -0.5876 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.6542 2.5459 2.1533 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.1461 0.0424 2.3070 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.1630 3.8872 0.1124 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.9309 2.5621 -0.9309 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.8585 3.4142 0.3071 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.6175 2.8242 3.1710 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.8825 1.5222 2.8301 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.0385 3.1567 2.1724 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.3807 1.5126 5.8158 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.1184 0.5488 6.6419 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.6020 -0.2912 6.0816 H 0 0 0 0 0 0 0 0 0 0 0 0 2.7413 4.4936 0.5005 H 0 0 0 0 0 0 0 0 0 0 0 0 3.2764 3.4782 -0.9336 H 0 0 0 0 0 0 0 0 0 0 0 0 3.2313 4.4062 -3.0794 H 0 0 0 0 0 0 0 0 0 0 0 0 2.7442 6.1017 -3.2310 H 0 0 0 0 0 0 0 0 0 0 0 0 1.4473 4.9276 -3.0461 H 0 0 0 0 0 0 0 0 0 0 0 0 3.3798 -0.7017 0.8235 H 0 0 0 0 0 0 0 0 0 0 0 0 5.7532 -1.4244 1.1141 H 0 0 0 0 0 0 0 0 0 0 0 0 7.1944 -1.6651 -0.7939 H 0 0 0 0 0 0 0 0 0 0 0 0 6.3163 -1.1900 -3.0847 H 0 0 0 0 0 0 0 0 0 0 0 0 3.9750 -0.4818 -3.3237 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.3678 -4.1881 -3.2677 H 0 0 0 0 0 0 0 0 0 0 0 0 0.2461 -3.0969 -4.6408 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.4314 -3.6710 -4.5780 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 1 7 8 1 0 8 9 1 0 9 10 2 0 9 11 1 0 6 12 1 0 12 13 1 0 13 14 1 0 14 15 1 0 15 16 1 0 16 17 1 6 17 18 1 0 18 19 1 0 18 20 1 0 15 21 1 0 21 22 1 0 22 23 2 0 22 24 1 0 13 25 1 0 25 26 1 0 26 27 2 0 26 28 1 0 28 29 1 0 29 30 1 0 12 31 1 0 31 32 1 0 32 33 2 0 32 34 1 0 34 35 2 0 35 36 1 0 36 37 2 0 37 38 1 0 38 39 2 0 5 40 1 0 40 41 1 0 41 42 2 0 41 43 1 0 16 2 1 0 39 34 1 0 16 6 1 0 18 14 1 0 1 44 1 0 1 45 1 0 1 46 1 0 2 47 1 1 3 48 1 0 3 49 1 0 4 50 1 0 4 51 1 0 5 52 1 6 7 53 1 0 7 54 1 0 11 55 1 0 11 56 1 0 11 57 1 0 12 58 1 6 13 59 1 6 14 60 1 1 15 61 1 1 19 62 1 0 19 63 1 0 19 64 1 0 20 65 1 0 20 66 1 0 20 67 1 0 24 68 1 0 24 69 1 0 24 70 1 0 28 71 1 0 28 72 1 0 30 73 1 0 30 74 1 0 30 75 1 0 35 76 1 0 36 77 1 0 37 78 1 0 38 79 1 0 39 80 1 0 43 81 1 0 43 82 1 0 43 83 1 0 M END

Standard InCHIKey	RVDLUHBVRBFQRM-JUHDBQHNSA-N
Standard InCHI	InChI=1S/C31H40O12/c1-17-13-14-22(39-19(3)33)30(16-38-18(2)32)27(42-28(36)21-11-9-8-10-12-21)25(41-23(35)15-37-7)24-26(40-20(4)34)31(17,30)43-29(24,5)6/h8-12,17,22,24-27H,13-16H2,1-7H3/t17-,22+,24-,25-,26-,27-,30+,31-/m1/s1
SMILES	C[C@@H]1CC[C@@H]([C@@]2(COC(=O)C)[C@@H]([C@@H]([C@@H]3[C@H]([C@]12OC3(C)C)OC(=O)C)OC(=O)COC)OC(=O)c1ccccc1)OC(=O)C

Calculated Properties

Physi-Chem Properties

Molecular Weight:	604.25	Volume:	594.897 ? Van der Waals volume.
Dense:	1.016	LogP:	2.781 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	2.839 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.121 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	14.0	Rigid Bonds:	25.0
TPSA:	149.96 ? Topological Polar Surface Area.	H-Bond Acceptor:	12.0
H-Bond Donor:	0.0	Rings:	4.0
Heavy Atoms:	12.0

MedChem Properties

QED Drug-Likeness Score:	0.301	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.872	Fsp³:	0.645
MCE-18:	146.235 ? 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:	0.314	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:	0.07 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.219	Promiscuous compounds:	0.197

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-4.982	MDCK Permeability:	-4.852
Pgp-inhibitor:	0.991	Pgp-substrate:	0.574
PAMPA:	0.539 ? 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):	0.0
20% Bioavailability (F20%):	0.043	30% Bioavailability (F30%):	0.338
50% Bioavailability (F50%):	0.978

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.59	MRP1:	0.999
Plasma Protein Binding (PPB):	60.57%	Volume Distribution (VD):	-0.214
Fu:	40.864% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.999
OATP1B3 inhibitor:	0.972	BCRP inhibitor:	0.004
BSEP inhibitor:	0.928

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.177
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.028
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.121
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.14
CYP3A4-inhibitor:	0.001	CYP3A4-substrate:	0.179
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	1.0
HLM stability:	1.0 ? 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):

3.402

Half-life (T1/2):

0.762

ADMET: Toxicity

hERG Blockers:	0.049	hERG Blockers (10um):	0.215
Human Hepatotoxicity (H-HT):	0.155	Drug-induced Liver Injury (DILI):	0.594
AMES Toxicity:	0.782	Rat Oral Acute Toxicity:	0.299
Maximum Recommended Daily Dose:	0.206	Skin Sensitization:	0.992
Carcinogencity:	0.942	Eye Corrosion:	0.001
Eye Irritation:	0.138	Respiratory Toxicity:	0.041
Drug-induced Neurotoxicity:	0.314	Ototoxicity:	0.255
Hematotoxicity:	0.163	Drug-induced Nephrotoxicity:	0.879
Genotoxicity:	0.196	RPMI-8226 Immunitoxicity:	0.125
A549 Cytotoxicity:	0.033	Hek293 Cytotoxicity:	0.177
BCF:	0.566 ? 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:	3.44 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.063 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.499 ? 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
NPO40494	Maytenus bilocularis	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[27120798]

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
Non-molecular	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
NPT20529	Non-molecular	NON-PROTEIN TARGET	n.a.	Inhibition	>	30.0	%	PMID[27120798]

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 NPC483848 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	15154
0.1-0.2	32761
0.2-0.3	1461
0.3-0.4	327
0.4-0.5	93
0.5-0.6	33
0.6-0.7	19
0.7-0.8	0
0.8-0.85	2
0.85-0.9	2
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.8769	High Similarity	NPC90257
0.8769	High Similarity	NPC69357
0.8485	Intermediate Similarity	NPC483845
0.8382	Intermediate Similarity	NPC483844
0.7671	Intermediate Similarity	NPC483849
0.6857	Remote Similarity	NPC66761
0.6857	Remote Similarity	NPC483843
0.6622	Remote Similarity	NPC483842
0.662	Remote Similarity	NPC211137
0.662	Remote Similarity	NPC476094
0.6579	Remote Similarity	NPC481059
0.6575	Remote Similarity	NPC473060
0.6575	Remote Similarity	NPC17877
0.6463	Remote Similarity	NPC473115
0.64	Remote Similarity	NPC137718
0.64	Remote Similarity	NPC148062
0.6389	Remote Similarity	NPC475429
0.6364	Remote Similarity	NPC479043
0.6351	Remote Similarity	NPC51314
0.6267	Remote Similarity	NPC147880
0.6234	Remote Similarity	NPC306146
0.6234	Remote Similarity	NPC483841
0.6154	Remote Similarity	NPC252314
0.6104	Remote Similarity	NPC473758
0.5904	Remote Similarity	NPC488900
0.5904	Remote Similarity	NPC479040
0.5904	Remote Similarity	NPC488899
0.5844	Remote Similarity	NPC48017
0.5778	Remote Similarity	NPC488902
0.5778	Remote Similarity	NPC488903
0.5769	Remote Similarity	NPC483846
0.575	Remote Similarity	NPC57628
0.5696	Remote Similarity	NPC473088
0.5641	Remote Similarity	NPC246480
0.5584	Remote Similarity	NPC90614
0.557	Remote Similarity	NPC147217
0.5556	Remote Similarity	NPC472569
0.5443	Remote Similarity	NPC4341
0.5443	Remote Similarity	NPC479047
0.5443	Remote Similarity	NPC291638
0.5412	Remote Similarity	NPC4421
0.5366	Remote Similarity	NPC16912
0.5325	Remote Similarity	NPC481047
0.5325	Remote Similarity	NPC481045
0.5263	Remote Similarity	NPC474608
0.525	Remote Similarity	NPC191082
0.5244	Remote Similarity	NPC479044
0.5233	Remote Similarity	NPC212768
0.5181	Remote Similarity	NPC11685
0.5181	Remote Similarity	NPC472570
0.5122	Remote Similarity	NPC254558
0.5122	Remote Similarity	NPC471107
0.5116	Remote Similarity	NPC481488
0.5116	Remote Similarity	NPC481486
0.5065	Remote Similarity	NPC283375
0.5065	Remote Similarity	NPC183122
0.506	Remote Similarity	NPC41481

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC483848 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	3781
0.1-0.2	5245
0.2-0.3	124
0.3-0.4	0
0.4-0.5	0
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