NPASS Compound

Structure

CID321514 OpenBabel06191716152D 36 37 0 0 1 0 0 0 0 0999 V2000 3.4641 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7321 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2321 -0.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4641 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5000 0.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0000 3.4641 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9641 1.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 1.7321 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9641 1.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5000 0.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 1.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.4641 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8660 -0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8660 -0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.4641 2.7321 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5000 2.5981 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 1.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.9641 3.5981 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.4641 2.7321 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 3.4641 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.5000 2.5981 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 20 2 0 0 0 0 2 20 1 0 0 0 0 3 21 1 0 0 0 0 4 22 2 0 0 0 0 5 29 1 0 0 0 0 6 29 1 0 0 0 0 9 36 1 0 0 0 0 10 12 1 0 0 0 0 10 21 2 0 0 0 0 11 15 1 0 0 0 0 11 22 1 0 0 0 0 12 23 1 0 0 0 0 13 14 1 0 0 0 0 13 24 1 0 0 0 0 14 25 1 0 0 0 0 15 26 1 0 0 0 0 16 18 1 0 0 0 0 16 27 1 0 0 0 0 17 19 1 0 0 0 0 17 28 1 0 0 0 0 18 30 1 0 0 0 0 19 31 1 0 0 0 0 20 23 1 0 0 0 0 21 24 1 0 0 0 0 22 25 1 0 0 0 0 23 30 1 6 0 0 0 24 30 1 6 0 0 0 25 31 1 1 0 0 0 26 29 1 0 0 0 0 26 31 1 1 0 0 0 27 32 2 0 0 0 0 27 33 1 0 0 0 0 28 34 2 0 0 0 0 28 36 1 0 0 0 0 29 35 1 0 0 0 0 30 7 1 6 0 0 0 31 8 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	502.37
Volume:	558.388
LogP:	5.792
LogD:	4.351
LogS:	-4.841
# Rotatable Bonds:	12
TPSA:	83.83
# H-Bond Aceptor:	5
# H-Bond Donor:	2
# Rings:	2
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.232
Synthetic Accessibility Score:	5.043
Fsp3:	0.742
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.129
MDCK Permeability:	1.145975875260774e-05
Pgp-inhibitor:	0.464
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.008
20% Bioavailability (F20%):	0.915
30% Bioavailability (F30%):	0.076

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.055
Plasma Protein Binding (PPB):	86.48749542236328%
Volume Distribution (VD):	0.446
Pgp-substrate:	8.730681419372559%

ADMET: Metabolism

CYP1A2-inhibitor:	0.018
CYP1A2-substrate:	0.136
CYP2C19-inhibitor:	0.015
CYP2C19-substrate:	0.341
CYP2C9-inhibitor:	0.142
CYP2C9-substrate:	0.874
CYP2D6-inhibitor:	0.008
CYP2D6-substrate:	0.277
CYP3A4-inhibitor:	0.248
CYP3A4-substrate:	0.187

ADMET: Excretion

Clearance (CL):	5.603
Half-life (T1/2):	0.411

ADMET: Toxicity

hERG Blockers:	0.018
Human Hepatotoxicity (H-HT):	0.52
Drug-inuced Liver Injury (DILI):	0.035
AMES Toxicity:	0.004
Rat Oral Acute Toxicity:	0.144
Maximum Recommended Daily Dose:	0.885
Skin Sensitization:	0.227
Carcinogencity:	0.128
Eye Corrosion:	0.009
Eye Irritation:	0.034
Respiratory Toxicity:	0.936

Download Data

Data Type	Select
General Info & Identifiers & Properties
Structure MOL file
Source Organisms
Biological Activities
Similar NPs/Drugs

Natural Product: NPC321514

Natural Product ID:	NPC321514
*Common Name:**	Lamesticumin A
IUPAC Name:	3-[(1S,2S,6S)-2-[2-[(1S,2R,3R)-3-(2-hydroxypropan-2-yl)-2-(3-methoxy-3-oxopropyl)-2-methyl-6-methylidenecyclohexyl]ethyl]-1,3-dimethyl-6-prop-1-en-2-ylcyclohex-3-en-1-yl]propanoic acid
Synonyms:	Lamesticumin A
Standard InCHIKey:	WWMHSLBXALTJEY-YTASFOGUSA-N
Standard InCHI:	InChI=1S/C31H50O5/c1-20(2)23-12-10-21(3)24(30(23,7)18-16-27(32)33)13-14-25-22(4)11-15-26(29(5,6)35)31(25,8)19-17-28(34)36-9/h10,23-26,35H,1,4,11-19H2,2-3,5-9H3,(H,32,33)/t23-,24-,25-,26-,30-,31+/m0/s1
SMILES:	CC1=CCC(C(C1CCC2C(=C)CCC(C2(C)CCC(=O)OC)C(C)(C)O)(C)CCC(=O)O)C(=C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1782129
PubChem CID:	53262846
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001549] Monoterpenoids [CHEMONTID:0001401] Menthane monoterpenoids

*Note: the InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.
**Note: the Chemical Classification was calculated by NPClassifier Version 1.5. Reference: PMID:34662515.

Species Source

Organism ID	Organism Name	Taxonomy Level	Family	SuperKingdom	Isolation Part	Collection Location	Collection Time	Reference
NPO20633	Lansium domesticum	Species	Meliaceae	Eukaryota	n.a.	exocarp	n.a.	DOI[10.1021/jo00172a004]
NPO20633	Lansium domesticum	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12444710]
NPO20633	Lansium domesticum	Species	Meliaceae	Eukaryota	seeds	n.a.	n.a.	PMID[19299148]
NPO20633	Lansium domesticum	Species	Meliaceae	Eukaryota	twigs	Xishuangbanna, Mengla County, Yunnan Province, China	2005-AUG	PMID[21401117]
NPO20633	Lansium domesticum	Species	Meliaceae	Eukaryota	n.a.	twig	n.a.	PMID[21401117]
NPO20633	Lansium domesticum	Species	Meliaceae	Eukaryota	Leaves	n.a.	n.a.	PMID[30335380]
NPO20633	Lansium domesticum	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	NP ID	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
MIC	11

Activity Type	# Activity
Organism	11

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	=	6.25	ug.mL-1	PMID[551574]
NPT1277	Organism	Staphylococcus epidermidis ATCC 12228	Staphylococcus epidermidis ATCC 12228	MIC	=	12.5	ug.mL-1	PMID[551574]
NPT729	Organism	Micrococcus luteus	Micrococcus luteus	MIC	=	6.25	ug.mL-1	PMID[551574]
NPT79	Organism	Bacillus subtilis	Bacillus subtilis	MIC	=	3.12	ug.mL-1	PMID[551574]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	=	3.12	ug.mL-1	PMID[551574]
NPT314	Organism	Bacillus cereus	Bacillus cereus	MIC	=	3.12	ug.mL-1	PMID[551574]
NPT19	Organism	Escherichia coli	Escherichia coli	MIC	>	50.0	ug.mL-1	PMID[551574]
NPT2909	Organism	Shigella flexneri	Shigella flexneri	MIC	>	50.0	ug.mL-1	PMID[551574]
NPT18	Organism	Pseudomonas aeruginosa	Pseudomonas aeruginosa	MIC	>	50.0	ug.mL-1	PMID[551574]
NPT1248	Organism	Serratia marcescens	Serratia marcescens	MIC	>	50.0	ug.mL-1	PMID[551574]
NPT2227	Organism	Alcaligenes faecalis	Alcaligenes faecalis	MIC	>	50.0	ug.mL-1	PMID[551574]

☑ Note for Activity Records:
☉ The quantitative biological activities were primarily integrated from ChEMBL (Version-30) database and were also directly collected from PubMed literature. PubMed PMID was provided as the reference link for each activity record.

Chemically structural similarity: I. Similar Active Natural Products in NPASS

Top-200 similar NPs were calculated against the active-NP-set (includes 4,3285 NPs with experimentally-derived bioactivity available in NPASS)

Similarity level is defined by Tanimoto coefficient (Tc) between two molecules. Tc lies between [0, 1] where '1' indicates the highest similarity. What is Tanimoto coefficient

● The left chart: Distribution of similarity level between NPC321514 and all remaining natural products in the NPASS database.
● The right table: Most similar natural products (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	156
0.1-0.2	1003
0.2-0.3	4932
0.3-0.4	14958
0.4-0.5	8628
0.5-0.6	6431
0.6-0.7	4793
0.7-0.8	1605
0.8-0.85	152
0.85-0.9	34
0.9-0.95	3
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.96	High Similarity	NPC327002
0.9333	High Similarity	NPC327674
0.9211	High Similarity	NPC104545
0.9211	High Similarity	NPC37038
0.92	High Similarity	NPC179028
0.9167	High Similarity	NPC160817
0.9079	High Similarity	NPC231431
0.9	High Similarity	NPC73038
0.9	High Similarity	NPC324063
0.8987	High Similarity	NPC156981
0.8961	High Similarity	NPC477057
0.8947	High Similarity	NPC110094
0.8947	High Similarity	NPC280654
0.8947	High Similarity	NPC260385
0.8933	High Similarity	NPC180886
0.8861	High Similarity	NPC477373
0.8861	High Similarity	NPC200752
0.8846	High Similarity	NPC278459
0.8846	High Similarity	NPC142244
0.8831	High Similarity	NPC199595
0.8831	High Similarity	NPC477371
0.8816	High Similarity	NPC107039
0.8816	High Similarity	NPC471899
0.8816	High Similarity	NPC471897
0.88	High Similarity	NPC192540
0.88	High Similarity	NPC279666
0.8765	High Similarity	NPC262085
0.8734	High Similarity	NPC133391
0.8701	High Similarity	NPC74410
0.8684	High Similarity	NPC309399
0.8684	High Similarity	NPC89294
0.8684	High Similarity	NPC69143
0.8684	High Similarity	NPC899
0.8667	High Similarity	NPC183503
0.8667	High Similarity	NPC166797
0.8667	High Similarity	NPC161923
0.8667	High Similarity	NPC241854
0.8667	High Similarity	NPC103958
0.8667	High Similarity	NPC306928
0.8667	High Similarity	NPC283908
0.8667	High Similarity	NPC301065
0.8667	High Similarity	NPC476046
0.8667	High Similarity	NPC251970
0.8659	High Similarity	NPC167877
0.8659	High Similarity	NPC128644
0.8608	High Similarity	NPC473420
0.8608	High Similarity	NPC229584
0.8608	High Similarity	NPC38350
0.8608	High Similarity	NPC201912
0.8608	High Similarity	NPC14203
0.8608	High Similarity	NPC162632
0.8608	High Similarity	NPC221647
0.8608	High Similarity	NPC40228
0.8608	High Similarity	NPC263272
0.8608	High Similarity	NPC274050
0.8608	High Similarity	NPC477372
0.8608	High Similarity	NPC267691
0.8608	High Similarity	NPC471898
0.8608	High Similarity	NPC147066
0.859	High Similarity	NPC16394
0.8571	High Similarity	NPC165711
0.8571	High Similarity	NPC472300
0.8554	High Similarity	NPC472870
0.8553	High Similarity	NPC476795
0.8553	High Similarity	NPC476844
0.8537	High Similarity	NPC325594
0.8537	High Similarity	NPC322159
0.8519	High Similarity	NPC165064
0.8519	High Similarity	NPC96095
0.85	High Similarity	NPC251779
0.85	High Similarity	NPC296367
0.85	High Similarity	NPC240302
0.85	High Similarity	NPC260956
0.85	High Similarity	NPC69101
0.8493	Intermediate Similarity	NPC290445
0.8493	Intermediate Similarity	NPC36616
0.8481	Intermediate Similarity	NPC267517
0.8462	Intermediate Similarity	NPC471409
0.8462	Intermediate Similarity	NPC239098
0.8462	Intermediate Similarity	NPC4827
0.8462	Intermediate Similarity	NPC275494
0.8452	Intermediate Similarity	NPC476733
0.8452	Intermediate Similarity	NPC215029
0.8452	Intermediate Similarity	NPC474700
0.8452	Intermediate Similarity	NPC36668
0.8452	Intermediate Similarity	NPC118011
0.8452	Intermediate Similarity	NPC474570
0.8434	Intermediate Similarity	NPC171722
0.8434	Intermediate Similarity	NPC173089
0.8434	Intermediate Similarity	NPC158141
0.8434	Intermediate Similarity	NPC96496
0.8434	Intermediate Similarity	NPC136948
0.8421	Intermediate Similarity	NPC237591
0.8421	Intermediate Similarity	NPC18819
0.8421	Intermediate Similarity	NPC46610
0.8421	Intermediate Similarity	NPC3753
0.8415	Intermediate Similarity	NPC76333
0.8415	Intermediate Similarity	NPC474680
0.8415	Intermediate Similarity	NPC269638
0.8395	Intermediate Similarity	NPC83569
0.8395	Intermediate Similarity	NPC476100
0.8395	Intermediate Similarity	NPC70834
0.8395	Intermediate Similarity	NPC69279
0.8395	Intermediate Similarity	NPC97913
0.8395	Intermediate Similarity	NPC310470
0.8375	Intermediate Similarity	NPC117960
0.8375	Intermediate Similarity	NPC476988
0.8375	Intermediate Similarity	NPC90055
0.8375	Intermediate Similarity	NPC172309
0.8375	Intermediate Similarity	NPC14044
0.8354	Intermediate Similarity	NPC196827
0.8354	Intermediate Similarity	NPC274996
0.8354	Intermediate Similarity	NPC28319
0.8354	Intermediate Similarity	NPC158846
0.8353	Intermediate Similarity	NPC476437
0.8353	Intermediate Similarity	NPC111585
0.8353	Intermediate Similarity	NPC476369
0.8353	Intermediate Similarity	NPC471896
0.8353	Intermediate Similarity	NPC474728
0.8353	Intermediate Similarity	NPC198818
0.8353	Intermediate Similarity	NPC113989
0.8353	Intermediate Similarity	NPC120840
0.8353	Intermediate Similarity	NPC175628
0.8353	Intermediate Similarity	NPC148414
0.8333	Intermediate Similarity	NPC1753
0.8333	Intermediate Similarity	NPC61952
0.8333	Intermediate Similarity	NPC24816
0.8333	Intermediate Similarity	NPC474474
0.8333	Intermediate Similarity	NPC40552
0.8333	Intermediate Similarity	NPC294480
0.8333	Intermediate Similarity	NPC474511
0.8333	Intermediate Similarity	NPC52169
0.8333	Intermediate Similarity	NPC325946
0.8333	Intermediate Similarity	NPC246708
0.8333	Intermediate Similarity	NPC97377
0.8333	Intermediate Similarity	NPC182797
0.8313	Intermediate Similarity	NPC476104
0.8313	Intermediate Similarity	NPC473226
0.8313	Intermediate Similarity	NPC155011
0.8313	Intermediate Similarity	NPC472869
0.8293	Intermediate Similarity	NPC164577
0.8293	Intermediate Similarity	NPC100391
0.8293	Intermediate Similarity	NPC472865
0.8289	Intermediate Similarity	NPC35656
0.8272	Intermediate Similarity	NPC73882
0.8272	Intermediate Similarity	NPC15910
0.8272	Intermediate Similarity	NPC320514
0.8267	Intermediate Similarity	NPC91369
0.8256	Intermediate Similarity	NPC26888
0.8256	Intermediate Similarity	NPC297265
0.8256	Intermediate Similarity	NPC470590
0.8256	Intermediate Similarity	NPC77099
0.8256	Intermediate Similarity	NPC154101
0.8256	Intermediate Similarity	NPC60755
0.8256	Intermediate Similarity	NPC285184
0.825	Intermediate Similarity	NPC2482
0.8235	Intermediate Similarity	NPC270768
0.8235	Intermediate Similarity	NPC474889
0.8235	Intermediate Similarity	NPC61543
0.8235	Intermediate Similarity	NPC225585
0.8235	Intermediate Similarity	NPC477973
0.8235	Intermediate Similarity	NPC198664
0.8235	Intermediate Similarity	NPC475921
0.8235	Intermediate Similarity	NPC121798
0.8235	Intermediate Similarity	NPC234346
0.8235	Intermediate Similarity	NPC263393
0.8235	Intermediate Similarity	NPC5509
0.8235	Intermediate Similarity	NPC262043
0.8235	Intermediate Similarity	NPC471342
0.8235	Intermediate Similarity	NPC127689
0.8235	Intermediate Similarity	NPC64872
0.8235	Intermediate Similarity	NPC470588
0.8235	Intermediate Similarity	NPC474704
0.8235	Intermediate Similarity	NPC59263
0.8235	Intermediate Similarity	NPC130520
0.8235	Intermediate Similarity	NPC274330
0.8235	Intermediate Similarity	NPC281524
0.8235	Intermediate Similarity	NPC25906
0.8235	Intermediate Similarity	NPC290972
0.8235	Intermediate Similarity	NPC469866
0.8235	Intermediate Similarity	NPC293048
0.8235	Intermediate Similarity	NPC30522
0.8235	Intermediate Similarity	NPC143232
0.8228	Intermediate Similarity	NPC198240
0.8228	Intermediate Similarity	NPC59436
0.8214	Intermediate Similarity	NPC142415
0.8214	Intermediate Similarity	NPC307426
0.8214	Intermediate Similarity	NPC159046
0.8214	Intermediate Similarity	NPC88716
0.8214	Intermediate Similarity	NPC51700
0.8214	Intermediate Similarity	NPC102683
0.8214	Intermediate Similarity	NPC71507
0.8214	Intermediate Similarity	NPC233836
0.8214	Intermediate Similarity	NPC187376
0.8214	Intermediate Similarity	NPC312215
0.8214	Intermediate Similarity	NPC68160
0.8214	Intermediate Similarity	NPC171203
0.8214	Intermediate Similarity	NPC293564
0.8214	Intermediate Similarity	NPC130577
0.8214	Intermediate Similarity	NPC242468

Chemically structural similarity: II. Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC321514 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	138
0.1-0.2	1489
0.2-0.3	3825
0.3-0.4	2418
0.4-0.5	737
0.5-0.6	286
0.6-0.7	193
0.7-0.8	64
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
0.8161	Intermediate Similarity	NPD6399	Phase 3
0.8068	Intermediate Similarity	NPD7748	Approved
0.8046	Intermediate Similarity	NPD7515	Phase 2
0.8	Intermediate Similarity	NPD6083	Phase 2
0.8	Intermediate Similarity	NPD6084	Phase 2
0.7978	Intermediate Similarity	NPD5695	Phase 3
0.7907	Intermediate Similarity	NPD5737	Approved
0.7907	Intermediate Similarity	NPD6672	Approved
0.7882	Intermediate Similarity	NPD7146	Approved
0.7882	Intermediate Similarity	NPD5330	Approved
0.7882	Intermediate Similarity	NPD6098	Approved
0.7882	Intermediate Similarity	NPD6409	Approved
0.7882	Intermediate Similarity	NPD7521	Approved
0.7882	Intermediate Similarity	NPD7334	Approved
0.7882	Intermediate Similarity	NPD6684	Approved
0.7857	Intermediate Similarity	NPD4786	Approved
0.7841	Intermediate Similarity	NPD5281	Approved
0.7841	Intermediate Similarity	NPD5284	Approved
0.7831	Intermediate Similarity	NPD4221	Approved
0.7831	Intermediate Similarity	NPD3667	Approved
0.7831	Intermediate Similarity	NPD4223	Phase 3
0.7816	Intermediate Similarity	NPD7285	Clinical (unspecified phase)
0.7816	Intermediate Similarity	NPD6904	Approved
0.7816	Intermediate Similarity	NPD6673	Approved
0.7816	Intermediate Similarity	NPD6080	Approved
0.7805	Intermediate Similarity	NPD4695	Discontinued
0.7802	Intermediate Similarity	NPD7902	Approved
0.7765	Intermediate Similarity	NPD5329	Approved
0.7717	Intermediate Similarity	NPD5696	Approved
0.7701	Intermediate Similarity	NPD6903	Approved
0.7701	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.7647	Intermediate Similarity	NPD4197	Approved
0.7647	Intermediate Similarity	NPD3133	Approved
0.7647	Intermediate Similarity	NPD3666	Approved
0.7647	Intermediate Similarity	NPD3665	Phase 1
0.764	Intermediate Similarity	NPD6050	Approved
0.764	Intermediate Similarity	NPD6411	Approved
0.7619	Intermediate Similarity	NPD4752	Clinical (unspecified phase)
0.7614	Intermediate Similarity	NPD4753	Phase 2
0.7586	Intermediate Similarity	NPD3573	Approved
0.7582	Intermediate Similarity	NPD6356	Clinical (unspecified phase)
0.7528	Intermediate Similarity	NPD5692	Phase 3
0.75	Intermediate Similarity	NPD5208	Approved
0.7473	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.7473	Intermediate Similarity	NPD7900	Approved
0.7471	Intermediate Similarity	NPD4688	Approved
0.7471	Intermediate Similarity	NPD4623	Approved
0.7471	Intermediate Similarity	NPD5280	Approved
0.7471	Intermediate Similarity	NPD4693	Phase 3
0.7471	Intermediate Similarity	NPD5205	Approved
0.7471	Intermediate Similarity	NPD4690	Approved
0.7471	Intermediate Similarity	NPD4519	Discontinued
0.7471	Intermediate Similarity	NPD4138	Approved
0.7471	Intermediate Similarity	NPD4694	Approved
0.7471	Intermediate Similarity	NPD4689	Approved
0.7471	Intermediate Similarity	NPD5690	Phase 2
0.7471	Intermediate Similarity	NPD3574	Clinical (unspecified phase)
0.7471	Intermediate Similarity	NPD3618	Phase 1
0.7444	Intermediate Similarity	NPD5694	Approved
0.7444	Intermediate Similarity	NPD5693	Phase 1
0.7442	Intermediate Similarity	NPD3668	Phase 3
0.7423	Intermediate Similarity	NPD6675	Approved
0.7423	Intermediate Similarity	NPD7128	Approved
0.7423	Intermediate Similarity	NPD6402	Approved
0.7423	Intermediate Similarity	NPD5739	Approved
0.7416	Intermediate Similarity	NPD6101	Approved
0.7416	Intermediate Similarity	NPD5764	Clinical (unspecified phase)
0.7416	Intermediate Similarity	NPD5328	Approved
0.7356	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.7349	Intermediate Similarity	NPD3617	Approved
0.7333	Intermediate Similarity	NPD5207	Approved
0.7312	Intermediate Similarity	NPD7614	Phase 1
0.7294	Intermediate Similarity	NPD4139	Approved
0.7294	Intermediate Similarity	NPD4692	Approved
0.7273	Intermediate Similarity	NPD7331	Phase 2
0.7273	Intermediate Similarity	NPD6881	Approved
0.7273	Intermediate Similarity	NPD5279	Phase 3
0.7273	Intermediate Similarity	NPD7320	Approved
0.7273	Intermediate Similarity	NPD6899	Approved
0.7253	Intermediate Similarity	NPD8034	Phase 2
0.7253	Intermediate Similarity	NPD6079	Approved
0.7253	Intermediate Similarity	NPD8035	Phase 2
0.725	Intermediate Similarity	NPD4243	Approved
0.7204	Intermediate Similarity	NPD5210	Approved
0.7204	Intermediate Similarity	NPD4629	Approved
0.72	Intermediate Similarity	NPD6373	Approved
0.72	Intermediate Similarity	NPD6372	Approved
0.7195	Intermediate Similarity	NPD8039	Approved
0.7174	Intermediate Similarity	NPD5778	Approved
0.7174	Intermediate Similarity	NPD5779	Approved
0.7174	Intermediate Similarity	NPD4202	Approved
0.7172	Intermediate Similarity	NPD5701	Approved
0.7172	Intermediate Similarity	NPD5697	Approved
0.7158	Intermediate Similarity	NPD7638	Approved
0.7143	Intermediate Similarity	NPD5784	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD7341	Phase 2
0.7129	Intermediate Similarity	NPD7102	Approved
0.7129	Intermediate Similarity	NPD6883	Approved
0.7129	Intermediate Similarity	NPD7290	Approved
0.7128	Intermediate Similarity	NPD7732	Phase 3
0.7126	Intermediate Similarity	NPD4788	Approved
0.71	Intermediate Similarity	NPD6011	Approved
0.7097	Intermediate Similarity	NPD6001	Approved
0.7093	Intermediate Similarity	NPD5369	Approved
0.7083	Intermediate Similarity	NPD7639	Approved
0.7083	Intermediate Similarity	NPD7640	Approved
0.7073	Intermediate Similarity	NPD4784	Approved
0.7073	Intermediate Similarity	NPD4785	Approved
0.7059	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD6869	Approved
0.7059	Intermediate Similarity	NPD6617	Approved
0.7059	Intermediate Similarity	NPD6650	Approved
0.7059	Intermediate Similarity	NPD6847	Approved
0.7059	Intermediate Similarity	NPD6649	Approved
0.7059	Intermediate Similarity	NPD7645	Phase 2
0.7059	Intermediate Similarity	NPD8130	Phase 1
0.7059	Intermediate Similarity	NPD4195	Approved
0.7053	Intermediate Similarity	NPD4755	Approved
0.7033	Intermediate Similarity	NPD6051	Approved
0.703	Intermediate Similarity	NPD6014	Approved
0.703	Intermediate Similarity	NPD6013	Approved
0.703	Intermediate Similarity	NPD6012	Approved
0.7021	Intermediate Similarity	NPD5654	Approved
0.7	Intermediate Similarity	NPD4137	Phase 3
0.699	Remote Similarity	NPD8297	Approved
0.699	Remote Similarity	NPD6882	Approved
0.6988	Remote Similarity	NPD6942	Approved
0.6988	Remote Similarity	NPD7339	Approved
0.6977	Remote Similarity	NPD7525	Registered
0.6966	Remote Similarity	NPD1694	Approved
0.6957	Remote Similarity	NPD4096	Approved
0.6947	Remote Similarity	NPD4697	Phase 3
0.6947	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6947	Remote Similarity	NPD5221	Approved
0.6947	Remote Similarity	NPD5222	Approved
0.6932	Remote Similarity	NPD5362	Discontinued
0.6914	Remote Similarity	NPD4691	Approved
0.6914	Remote Similarity	NPD4747	Approved
0.6907	Remote Similarity	NPD4696	Approved
0.6907	Remote Similarity	NPD5285	Approved
0.6907	Remote Similarity	NPD6404	Discontinued
0.6907	Remote Similarity	NPD5286	Approved
0.6907	Remote Similarity	NPD4700	Approved
0.6905	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD5959	Approved
0.6875	Remote Similarity	NPD5173	Approved
0.6875	Remote Similarity	NPD3621	Clinical (unspecified phase)
0.6869	Remote Similarity	NPD6052	Approved
0.6867	Remote Similarity	NPD6926	Approved
0.6867	Remote Similarity	NPD6924	Approved
0.6867	Remote Similarity	NPD5733	Approved
0.6837	Remote Similarity	NPD5223	Approved
0.6835	Remote Similarity	NPD4224	Phase 2
0.6832	Remote Similarity	NPD6412	Phase 2
0.6829	Remote Similarity	NPD6081	Approved
0.6818	Remote Similarity	NPD6435	Approved
0.6809	Remote Similarity	NPD5133	Approved
0.6786	Remote Similarity	NPD5275	Approved
0.6786	Remote Similarity	NPD4190	Phase 3
0.6786	Remote Similarity	NPD3702	Approved
0.6782	Remote Similarity	NPD5368	Approved
0.6768	Remote Similarity	NPD5225	Approved
0.6768	Remote Similarity	NPD4633	Approved
0.6768	Remote Similarity	NPD5224	Approved
0.6768	Remote Similarity	NPD5211	Phase 2
0.6768	Remote Similarity	NPD5226	Approved
0.6765	Remote Similarity	NPD6686	Approved
0.6762	Remote Similarity	NPD4632	Approved
0.6742	Remote Similarity	NPD7154	Phase 3
0.6739	Remote Similarity	NPD4518	Approved
0.6733	Remote Similarity	NPD6008	Approved
0.6729	Remote Similarity	NPD7115	Discovery
0.6712	Remote Similarity	NPD4266	Approved
0.6712	Remote Similarity	NPD3196	Approved
0.6712	Remote Similarity	NPD3194	Approved
0.6712	Remote Similarity	NPD3195	Phase 2
0.6706	Remote Similarity	NPD6117	Approved
0.6706	Remote Similarity	NPD6933	Approved
0.6703	Remote Similarity	NPD6422	Discontinued
0.6702	Remote Similarity	NPD7637	Suspended
0.67	Remote Similarity	NPD4754	Approved
0.67	Remote Similarity	NPD5174	Approved
0.67	Remote Similarity	NPD5175	Approved
0.6667	Remote Similarity	NPD4687	Approved
0.6667	Remote Similarity	NPD6335	Approved
0.6667	Remote Similarity	NPD6113	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6614	Approved
0.6667	Remote Similarity	NPD4058	Approved
0.6636	Remote Similarity	NPD6868	Approved
0.6636	Remote Similarity	NPD6274	Approved
0.6634	Remote Similarity	NPD5141	Approved
0.6633	Remote Similarity	NPD4225	Approved
0.6629	Remote Similarity	NPD4269	Approved
0.6629	Remote Similarity	NPD4270	Approved
0.6628	Remote Similarity	NPD6116	Phase 1
0.6627	Remote Similarity	NPD5276	Approved
0.6606	Remote Similarity	NPD7101	Approved
0.6606	Remote Similarity	NPD7100	Approved
0.66	Remote Similarity	NPD5091	Approved
0.6596	Remote Similarity	NPD5785	Approved

Bioactivity similarity: Similar Natural Products in NPASS

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