NPASS Compound

Natural Product: NPC602263

Natural Product ID	NPC602263
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	ODLCLZLDYDHRGT-NEGPAABLSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL1075850
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 84 89 0 0 0 0 0 0 0 0999 V2000 1.1885 2.6771 4.1215 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9092 2.2451 2.9101 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0233 2.6808 2.5515 O 0 0 0 0 0 0 0 0 0 0 0 0 1.3614 1.2795 2.0552 O 0 0 0 0 0 0 0 0 0 0 0 0 1.9432 0.8011 0.8992 C 0 0 1 0 0 0 0 0 0 0 0 0 2.4210 -0.6279 1.0476 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5202 -0.8461 0.0570 C 0 0 1 0 0 0 0 0 0 0 0 0 3.8637 -2.1979 0.0649 O 0 0 0 0 0 0 0 0 0 0 0 0 5.1238 -2.6084 0.4628 C 0 0 0 0 0 0 0 0 0 0 0 0 5.5505 -4.0320 0.4934 C 0 0 0 0 0 0 0 0 0 0 0 0 5.9493 -1.7068 0.8184 O 0 0 0 0 0 0 0 0 0 0 0 0 3.1360 -0.3160 -1.3015 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3224 -1.5084 -2.2634 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0290 0.7439 -1.8220 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6718 -0.0433 -1.3152 C 0 0 2 0 0 0 0 0 0 0 0 0 1.0303 -0.0258 -2.6596 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4447 -0.3544 -2.4095 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.4041 -1.5324 -1.6333 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.9629 -2.7277 -1.9728 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8135 -3.8710 -1.0111 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5679 -2.8374 -3.0454 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.0427 0.7340 -1.5171 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.0388 1.9417 -2.4358 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2678 0.9013 -0.2707 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.9805 1.9420 0.5181 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1547 1.2457 1.1866 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8841 0.3487 0.2377 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.9083 -1.0896 0.7772 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3487 0.7668 0.2832 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.8860 0.9682 1.6430 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.2339 0.0208 2.5683 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.6812 0.6982 3.6804 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.5995 1.9725 3.4197 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.1351 2.1899 2.2272 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0670 -0.2805 -0.3553 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.6042 -0.8069 -1.5814 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.2061 -1.7103 -2.1912 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.3419 -0.2148 -2.1109 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.4378 1.2001 -2.0704 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.4696 0.4349 -1.1939 C 0 0 2 0 0 0 0 0 0 0 0 0 1.2231 1.0762 -0.3996 C 0 0 1 0 0 0 0 0 0 0 0 0 1.6230 2.4476 -0.8674 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5901 3.6050 3.9024 H 0 0 0 0 0 0 0 0 0 0 0 0 0.5655 1.8616 4.5194 H 0 0 0 0 0 0 0 0 0 0 0 0 1.9488 2.9991 4.8754 H 0 0 0 0 0 0 0 0 0 0 0 0 2.9237 1.3730 0.8282 H 0 0 0 0 0 0 0 0 0 0 0 0 2.9248 -0.6362 2.0632 H 0 0 0 0 0 0 0 0 0 0 0 0 1.6529 -1.3826 1.1108 H 0 0 0 0 0 0 0 0 0 0 0 0 4.3962 -0.2382 0.4061 H 0 0 0 0 0 0 0 0 0 0 0 0 6.4873 -4.1550 -0.1214 H 0 0 0 0 0 0 0 0 0 0 0 0 4.7784 -4.6714 0.0623 H 0 0 0 0 0 0 0 0 0 0 0 0 5.8196 -4.3537 1.5402 H 0 0 0 0 0 0 0 0 0 0 0 0 2.5352 -2.2636 -2.1158 H 0 0 0 0 0 0 0 0 0 0 0 0 4.2860 -2.0243 -1.9843 H 0 0 0 0 0 0 0 0 0 0 0 0 3.4474 -1.1751 -3.2973 H 0 0 0 0 0 0 0 0 0 0 0 0 3.6981 0.9952 -2.8531 H 0 0 0 0 0 0 0 0 0 0 0 0 5.0407 0.2584 -1.9794 H 0 0 0 0 0 0 0 0 0 0 0 0 4.2174 1.5953 -1.1768 H 0 0 0 0 0 0 0 0 0 0 0 0 1.2363 -0.9726 -0.8195 H 0 0 0 0 0 0 0 0 0 0 0 0 1.2149 0.8124 -3.2968 H 0 0 0 0 0 0 0 0 0 0 0 0 1.4235 -0.9383 -3.1982 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.9917 -0.4765 -3.3499 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.5266 -3.5035 -0.0110 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.8072 -4.3846 -0.8772 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.0271 -4.5739 -1.3435 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.6586 2.7742 -2.1344 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.5558 1.5574 -3.3761 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.0820 2.2826 -2.7845 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.3394 -0.0623 0.2870 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.4922 2.7136 -0.1355 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.4028 2.5316 1.2100 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.7624 2.0477 1.6284 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.7350 0.6645 2.0341 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.8546 -1.0609 1.9105 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.8736 -1.5969 0.5765 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.0389 -1.6826 0.5073 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.4881 1.7194 -0.3180 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.1794 -1.0788 2.4666 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.0403 0.2521 4.6139 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.9692 3.1866 1.7633 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0712 -0.5457 -3.1353 H 0 0 0 0 0 0 0 0 0 0 0 0 2.4168 2.8949 -0.1907 H 0 0 0 0 0 0 0 0 0 0 0 0 2.0992 2.4762 -1.8621 H 0 0 0 0 0 0 0 0 0 0 0 0 0.7846 3.1979 -0.7586 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 2 0 2 4 1 0 4 5 1 0 5 6 1 0 6 7 1 0 7 8 1 0 8 9 1 0 9 10 1 0 9 11 2 0 7 12 1 0 12 13 1 0 12 14 1 0 12 15 1 0 15 16 1 0 16 17 1 0 17 18 1 0 18 19 1 0 19 20 1 0 19 21 2 0 17 22 1 0 22 23 1 6 22 24 1 0 24 25 1 0 25 26 1 0 26 27 1 0 27 28 1 1 27 29 1 0 29 30 1 0 30 31 1 0 31 32 2 0 32 33 1 0 33 34 1 0 29 35 1 0 35 36 1 0 36 37 2 0 36 38 1 0 38 39 1 0 40 39 1 6 24 41 1 0 41 42 1 6 41 5 1 0 41 15 1 0 40 22 1 0 40 27 1 0 34 30 2 0 40 38 1 0 1 43 1 0 1 44 1 0 1 45 1 0 5 46 1 6 6 47 1 0 6 48 1 0 7 49 1 1 10 50 1 0 10 51 1 0 10 52 1 0 13 53 1 0 13 54 1 0 13 55 1 0 14 56 1 0 14 57 1 0 14 58 1 0 15 59 1 1 16 60 1 0 16 61 1 0 17 62 1 6 20 63 1 0 20 64 1 0 20 65 1 0 23 66 1 0 23 67 1 0 23 68 1 0 24 69 1 1 25 70 1 0 25 71 1 0 26 72 1 0 26 73 1 0 28 74 1 0 28 75 1 0 28 76 1 0 29 77 1 6 31 78 1 0 32 79 1 0 34 80 1 0 38 81 1 6 42 82 1 0 42 83 1 0 42 84 1 0 M END

Standard InCHIKey	ODLCLZLDYDHRGT-NEGPAABLSA-N
Standard InCHI	InChI=1S/C32H42O10/c1-16(33)38-22-14-23(39-17(2)34)30(7)20-9-11-29(6)25(19-10-12-37-15-19)41-27(36)26-32(29,42-26)31(20,8)24(40-18(3)35)13-21(30)28(22,4)5/h10,12,15,20-26H,9,11,13-14H2,1-8H3/t20-,21+,22-,23+,24-,25+,26-,29+,30-,31+,32-/m1/s1
SMILES	CC(=O)O[C@H]1C[C@@H](OC(C)=O)C(C)(C)[C@@H]2C[C@@H](OC(C)=O)[C@]3(C)[C@H](CC[C@@]4(C)[C@H](c5ccoc5)OC(=O)[C@H]5O[C@@]534)[C@@]12C

Calculated Properties

Physi-Chem Properties

Molecular Weight:	586.28	Volume:	582.773 ? Van der Waals volume.
Dense:	1.006	LogP:	1.638 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	1.922 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-3.459 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	7.0	Rigid Bonds:	32.0
TPSA:	130.87 ? Topological Polar Surface Area.	H-Bond Acceptor:	10.0
H-Bond Donor:	0.0	Rings:	6.0
Heavy Atoms:	10.0

MedChem Properties

QED Drug-Likeness Score:	0.278	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.726	Fsp³:	0.75
MCE-18:	205.714 ? 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:	0
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.52	Fluc inhibitor:	0.002 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.011 ? 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:	0.205	Promiscuous compounds:	0.344

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.23	MDCK Permeability:	-4.937
Pgp-inhibitor:	1.0	Pgp-substrate:	0.07
PAMPA:	0.162 ? 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):	0.015
20% Bioavailability (F20%):	0.741	30% Bioavailability (F30%):	0.966
50% Bioavailability (F50%):	0.952

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.977
Plasma Protein Binding (PPB):	66.037%	Volume Distribution (VD):	-0.436
Fu:	32.617% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	0.979	BCRP inhibitor:	0.015
BSEP inhibitor:	0.996

ADMET: Metabolism

CYP1A2-inhibitor:	0.033	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.984	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.001
CYP3A4-inhibitor:	0.119	CYP3A4-substrate:	0.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.988
HLM stability:	0.693 ? 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):

4.63

Half-life (T1/2):

0.748

ADMET: Toxicity

hERG Blockers:	0.043	hERG Blockers (10um):	0.165
Human Hepatotoxicity (H-HT):	0.382	Drug-induced Liver Injury (DILI):	0.877
AMES Toxicity:	0.491	Rat Oral Acute Toxicity:	0.916
Maximum Recommended Daily Dose:	0.933	Skin Sensitization:	0.645
Carcinogencity:	0.715	Eye Corrosion:	0.002
Eye Irritation:	0.385	Respiratory Toxicity:	0.708
Drug-induced Neurotoxicity:	0.063	Ototoxicity:	0.454
Hematotoxicity:	0.322	Drug-induced Nephrotoxicity:	0.784
Genotoxicity:	0.985	RPMI-8226 Immunitoxicity:	0.123
A549 Cytotoxicity:	0.06	Hek293 Cytotoxicity:	0.052
BCF:	0.705 ? 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:	3.729 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.975 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	5.467 ? 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
NPO3494	Swietenia mahagoni	Species	Meliaceae	Eukaryota	fruits	n.a.	n.a.	PMID[19902967]
NPO58381	Khaya anthotheca	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO3494	Swietenia mahagoni	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO3494	Swietenia mahagoni	Species	Meliaceae	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	2
Activity	11

Activity Type	# Activity
Individual protein	2
Organism	11

Molecular-level activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT72	Individual protein	Solute carrier organic anion transporter family member 1B3	Homo sapiens	Inhibition	=	94.96	%	PMID[23571415]
NPT73	Individual protein	Solute carrier organic anion transporter family member 1B1	Homo sapiens	Inhibition	=	77.22	%	PMID[23571415]

In vitro activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT2909	Organism	Shigella flexneri	Shigella flexneri	Activity	n.a.	n.a.	n.a.	PMID[19902967]
NPT329	Organism	Trichophyton rubrum	Trichophyton rubrum	Activity	n.a.	n.a.	n.a.	PMID[19902967]
NPT20	Organism	Candida albicans	Candida albicans	Activity	n.a.	n.a.	n.a.	PMID[19902967]
NPT79	Organism	Bacillus subtilis	Bacillus subtilis	Activity	n.a.	n.a.	n.a.	PMID[19902967]
NPT19	Organism	Escherichia coli	Escherichia coli	Activity	n.a.	n.a.	n.a.	PMID[19902967]
NPT17	Organism	Staphylococcus epidermidis	Staphylococcus epidermidis	Activity	n.a.	n.a.	n.a.	PMID[19902967]
NPT18	Organism	Pseudomonas aeruginosa	Pseudomonas aeruginosa	Activity	n.a.	n.a.	n.a.	PMID[19902967]
NPT28601	Organism	Nannizzia gypsea	Nannizzia gypsea	Activity	n.a.	n.a.	n.a.	PMID[19902967]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	Activity	n.a.	n.a.	n.a.	PMID[19902967]
NPT1533	Organism	Saccharomyces	Saccharomyces	Activity	n.a.	n.a.	n.a.	PMID[19902967]
NPT3147	Organism	Kocuria rhizophila	Kocuria rhizophila	Activity	n.a.	n.a.	n.a.	PMID[19902967]

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 NPC602263 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	15028
0.1-0.2	32884
0.2-0.3	1683
0.3-0.4	199
0.4-0.5	26
0.5-0.6	23
0.6-0.7	7
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
0.7778	Intermediate Similarity	NPC134254
0.7778	Intermediate Similarity	NPC470939
0.7432	Intermediate Similarity	NPC302369
0.7237	Intermediate Similarity	NPC475381
0.7162	Intermediate Similarity	NPC107646
0.7067	Intermediate Similarity	NPC335761
0.6883	Remote Similarity	NPC209364
0.6883	Remote Similarity	NPC605015
0.6623	Remote Similarity	NPC39986
0.65	Remote Similarity	NPC126723
0.6429	Remote Similarity	NPC469846
0.6296	Remote Similarity	NPC472653
0.6265	Remote Similarity	NPC271235
0.5904	Remote Similarity	NPC237155
0.5696	Remote Similarity	NPC604270
0.5663	Remote Similarity	NPC286722
0.5568	Remote Similarity	NPC302392
0.5543	Remote Similarity	NPC472652
0.5529	Remote Similarity	NPC96443
0.5529	Remote Similarity	NPC473473
0.5529	Remote Similarity	NPC290400
0.5529	Remote Similarity	NPC475295
0.5444	Remote Similarity	NPC472651
0.5412	Remote Similarity	NPC609366
0.5412	Remote Similarity	NPC611370
0.5402	Remote Similarity	NPC473753
0.5366	Remote Similarity	NPC60973
0.5366	Remote Similarity	NPC605384
0.5357	Remote Similarity	NPC5079
0.5349	Remote Similarity	NPC473766
0.5281	Remote Similarity	NPC25255
0.5227	Remote Similarity	NPC117986
0.5172	Remote Similarity	NPC305016
0.5172	Remote Similarity	NPC282445
0.5116	Remote Similarity	NPC263265
0.5114	Remote Similarity	NPC611267

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC602263 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	4056
0.1-0.2	5068
0.2-0.3	26
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