NPASS Compound

Structure

NPC165538 OpenBabel07101719252D 44 46 0 0 1 0 0 0 0 0999 V2000 2.6942 -1.8801 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4296 4.6932 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6543 3.4684 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5418 -0.7187 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7140 4.5078 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9842 -0.7187 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2000 0.4971 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2000 3.0231 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9871 -1.1730 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3570 3.6563 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3693 3.8127 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.7153 2.7227 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2459 -0.2071 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7399 3.0356 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0860 1.9456 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4690 1.3249 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6266 2.8479 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6884 3.7273 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0878 0.1723 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.5575 3.5201 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.5302 0.1723 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.0983 2.1020 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5388 0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.0388 2.0388 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4813 1.4813 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.9813 3.0201 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.0388 1.4813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5302 3.3479 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0878 3.3479 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9813 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4813 2.0388 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5575 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 3.5201 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 1.8666 0.9511 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 1.0878 2.3479 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -1.3090 0.9511 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -1.3090 2.5691 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 3.0265 1.3249 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.9842 4.2389 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.6884 -0.2071 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.4690 2.1953 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.7140 -0.9877 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.0388 3.6569 0.0000 S 0 0 0 0 0 0 0 0 0 0 0 0 1 9 1 0 0 0 0 2 18 1 0 0 0 0 3 18 1 0 0 0 0 7 36 1 0 0 0 0 8 37 1 0 0 0 0 9 13 1 0 0 0 0 10 11 2 0 0 0 0 10 12 1 0 0 0 0 11 14 1 0 0 0 0 12 15 2 0 0 0 0 14 22 2 0 0 0 0 15 22 1 0 0 0 0 16 22 1 0 0 0 0 17 24 2 0 0 0 0 17 44 1 0 0 0 0 19 4 1 1 0 0 0 19 23 1 0 0 0 0 19 32 1 0 0 0 0 20 5 1 1 0 0 0 20 29 1 0 0 0 0 20 33 1 0 0 0 0 21 6 1 1 0 0 0 21 30 1 0 0 0 0 21 43 1 0 0 0 0 23 13 1 6 0 0 0 23 34 1 0 0 0 0 24 27 1 0 0 0 0 24 35 1 0 0 0 0 25 16 1 1 0 0 0 25 31 1 0 0 0 0 25 36 1 0 0 0 0 26 18 1 1 0 0 0 26 28 1 0 0 0 0 26 37 1 0 0 0 0 27 34 2 3 0 0 0 27 38 1 0 0 0 0 28 33 2 3 0 0 0 28 39 1 0 0 0 0 29 35 2 0 0 0 0 29 44 1 0 0 0 0 30 36 1 0 0 0 0 30 40 2 0 0 0 0 31 37 1 0 0 0 0 31 41 2 0 0 0 0 32 42 2 0 0 0 0 32 43 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	627.31
Volume:	636.228
LogP:	4.222
LogD:	3.483
LogS:	-4.557
# Rotatable Bonds:	5
TPSA:	138.01
# H-Bond Aceptor:	11
# H-Bond Donor:	2
# Rings:	3
# Heavy Atoms:	12

MedChem Properties

QED Drug-Likeness Score:	0.485
Synthetic Accessibility Score:	5.749
Fsp3:	0.562
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:	-4.956
MDCK Permeability:	1.8109320080839097e-05
Pgp-inhibitor:	0.999
Pgp-substrate:	0.56
Human Intestinal Absorption (HIA):	0.005
20% Bioavailability (F20%):	0.008
30% Bioavailability (F30%):	0.668

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.1
Plasma Protein Binding (PPB):	82.89850616455078%
Volume Distribution (VD):	0.412
Pgp-substrate:	13.005367279052734%

ADMET: Metabolism

CYP1A2-inhibitor:	0.037
CYP1A2-substrate:	0.09
CYP2C19-inhibitor:	0.492
CYP2C19-substrate:	0.654
CYP2C9-inhibitor:	0.761
CYP2C9-substrate:	0.057
CYP2D6-inhibitor:	0.024
CYP2D6-substrate:	0.101
CYP3A4-inhibitor:	0.938
CYP3A4-substrate:	0.83

ADMET: Excretion

Clearance (CL):	4.63
Half-life (T1/2):	0.056

ADMET: Toxicity

hERG Blockers:	0.007
Human Hepatotoxicity (H-HT):	0.966
Drug-inuced Liver Injury (DILI):	0.98
AMES Toxicity:	0.004
Rat Oral Acute Toxicity:	0.13
Maximum Recommended Daily Dose:	0.446
Skin Sensitization:	0.027
Carcinogencity:	0.018
Eye Corrosion:	0.003
Eye Irritation:	0.006
Respiratory Toxicity:	0.088

Download Data

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

Natural Product: NPC165538

Natural Product ID:	NPC165538
*Common Name:**	Ulongamide A
IUPAC Name:	(4R,5R,8S,11S,14S,17S)-11-benzyl-5,8,10,13,17-pentamethyl-14-propan-2-yl-4-propyl-7-oxa-19-thia-3,10,13,16,21-pentazabicyclo[16.2.1]henicosa-1(20),18(21)-diene-2,6,9,12,15-pentone
Synonyms:
Standard InCHIKey:	LKFYCKOJWDHZOF-XJRDRPONSA-N
Standard InCHI:	InChI=1S/C32H45N5O6S/c1-9-13-23-19(4)32(42)43-21(6)30(40)36(7)25(16-22-14-11-10-12-15-22)31(41)37(8)26(18(2)3)28(39)33-20(5)29-35-24(17-44-29)27(38)34-23/h10-12,14-15,17-21,23,25-26H,9,13,16H2,1-8H3,(H,33,39)(H,34,38)/t19-,20+,21+,23-,25+,26+/m1/s1
SMILES:	CCC[C@@H]1[C@@H](C)C(=O)O[C@@H](C)C(=O)N(C)[C@@H](Cc2ccccc2)C(=O)N(C)[C@@H](C(C)C)C(=N[C@@H](C)c2nc(cs2)C(=N1)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL505257
PubChem CID:	10985040
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000264] Organic acids and derivatives [CHEMONTID:0001813] Peptidomimetics [CHEMONTID:0001961] Depsipeptides [CHEMONTID:0001994] Cyclic depsipeptides

*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
NPO32881	Lyngbya sp.	Species	Oscillatoriaceae	Bacteria	n.a.	Palauan	n.a.	PMID[12141859]
NPO32881	Lyngbya sp.	Species	Oscillatoriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[12502348]
NPO32881	Lyngbya sp.	Species	Oscillatoriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[12762789]
NPO32881	Lyngbya sp.	Species	Oscillatoriaceae	Bacteria	n.a.	Palauan	n.a.	PMID[12762800]
NPO32881	Lyngbya sp.	Species	Oscillatoriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[14695793]
NPO32881	Lyngbya sp.	Species	Oscillatoriaceae	Bacteria	n.a.	Florida Everglades	n.a.	PMID[17432902]
NPO32881	Lyngbya sp.	Species	Oscillatoriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[18693761]
NPO32881	Lyngbya sp.	Species	Oscillatoriaceae	Bacteria	n.a.	Florida Keys	n.a.	PMID[21705224]

☑ 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
IC50	2

Activity Type	# Activity
Cell Line	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT91	Cell Line	KB	Homo sapiens	IC50	=	1000.0	nM	PMID[508802]
NPT114	Cell Line	LoVo	Homo sapiens	IC50	=	5000.0	nM	PMID[508802]

☑ 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 NPC165538 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	208
0.1-0.2	1686
0.2-0.3	10924
0.3-0.4	20987
0.4-0.5	6258
0.5-0.6	2186
0.6-0.7	404
0.7-0.8	37
0.8-0.85	0
0.85-0.9	1
0.9-0.95	3
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9766	High Similarity	NPC329961
0.9766	High Similarity	NPC122427
0.9189	High Similarity	NPC145178
0.9189	High Similarity	NPC475350
0.9189	High Similarity	NPC14877
0.9043	High Similarity	NPC251036
0.8251	Intermediate Similarity	NPC96016
0.8142	Intermediate Similarity	NPC161143
0.8022	Intermediate Similarity	NPC161242
0.7989	Intermediate Similarity	NPC24990
0.7935	Intermediate Similarity	NPC25316
0.7935	Intermediate Similarity	NPC229160
0.7935	Intermediate Similarity	NPC263485
0.7923	Intermediate Similarity	NPC476080
0.7923	Intermediate Similarity	NPC475534
0.7906	Intermediate Similarity	NPC106235
0.7906	Intermediate Similarity	NPC239660
0.788	Intermediate Similarity	NPC475330
0.7845	Intermediate Similarity	NPC476103
0.7838	Intermediate Similarity	NPC174652
0.7606	Intermediate Similarity	NPC475196
0.7586	Intermediate Similarity	NPC105717
0.7416	Intermediate Similarity	NPC286551
0.7413	Intermediate Similarity	NPC75498
0.7341	Intermediate Similarity	NPC263493
0.7341	Intermediate Similarity	NPC269398
0.734	Intermediate Similarity	NPC317362
0.734	Intermediate Similarity	NPC317725
0.734	Intermediate Similarity	NPC326407
0.734	Intermediate Similarity	NPC318930
0.7326	Intermediate Similarity	NPC98424
0.7326	Intermediate Similarity	NPC178662
0.7326	Intermediate Similarity	NPC470884
0.7326	Intermediate Similarity	NPC476133
0.7326	Intermediate Similarity	NPC92784
0.7314	Intermediate Similarity	NPC209509
0.7168	Intermediate Similarity	NPC471265
0.7168	Intermediate Similarity	NPC471264
0.7151	Intermediate Similarity	NPC283783
0.7039	Intermediate Similarity	NPC257511
0.7039	Intermediate Similarity	NPC319751
0.7022	Intermediate Similarity	NPC5620
0.7006	Intermediate Similarity	NPC139326
0.7	Intermediate Similarity	NPC469858
0.6983	Remote Similarity	NPC475390
0.6927	Remote Similarity	NPC322878
0.6923	Remote Similarity	NPC119481
0.691	Remote Similarity	NPC161069
0.6906	Remote Similarity	NPC240848
0.6872	Remote Similarity	NPC469801
0.6868	Remote Similarity	NPC129666
0.6868	Remote Similarity	NPC473398
0.6851	Remote Similarity	NPC329761
0.6851	Remote Similarity	NPC225648
0.6813	Remote Similarity	NPC471821
0.6813	Remote Similarity	NPC471820
0.6806	Remote Similarity	NPC475920
0.6798	Remote Similarity	NPC46098
0.6798	Remote Similarity	NPC268841
0.6798	Remote Similarity	NPC307357
0.6796	Remote Similarity	NPC262077
0.6791	Remote Similarity	NPC297145
0.6791	Remote Similarity	NPC197743
0.678	Remote Similarity	NPC68865
0.6758	Remote Similarity	NPC138775
0.6758	Remote Similarity	NPC145113
0.674	Remote Similarity	NPC313867
0.674	Remote Similarity	NPC316008
0.6739	Remote Similarity	NPC475168
0.6739	Remote Similarity	NPC7817
0.6718	Remote Similarity	NPC477462
0.6716	Remote Similarity	NPC329731
0.6716	Remote Similarity	NPC4910
0.6703	Remote Similarity	NPC162104
0.6703	Remote Similarity	NPC314358
0.6697	Remote Similarity	NPC313804
0.6697	Remote Similarity	NPC315804
0.6685	Remote Similarity	NPC52748
0.6685	Remote Similarity	NPC314388
0.6685	Remote Similarity	NPC315283
0.6685	Remote Similarity	NPC476978
0.6682	Remote Similarity	NPC79386
0.6649	Remote Similarity	NPC471051
0.6649	Remote Similarity	NPC471053
0.6649	Remote Similarity	NPC471052
0.6648	Remote Similarity	NPC89489
0.6631	Remote Similarity	NPC470902
0.663	Remote Similarity	NPC197682
0.6629	Remote Similarity	NPC300315
0.6612	Remote Similarity	NPC190329
0.6602	Remote Similarity	NPC59827
0.6602	Remote Similarity	NPC184933
0.6598	Remote Similarity	NPC101980
0.6598	Remote Similarity	NPC470146
0.6598	Remote Similarity	NPC97078
0.6595	Remote Similarity	NPC2501
0.6592	Remote Similarity	NPC127741
0.6579	Remote Similarity	NPC315252
0.6578	Remote Similarity	NPC122590
0.6576	Remote Similarity	NPC135121
0.6575	Remote Similarity	NPC168113
0.6573	Remote Similarity	NPC248283
0.6557	Remote Similarity	NPC477217
0.6557	Remote Similarity	NPC201244
0.6557	Remote Similarity	NPC214827
0.6557	Remote Similarity	NPC314930
0.6538	Remote Similarity	NPC176226
0.6538	Remote Similarity	NPC468984
0.6537	Remote Similarity	NPC477526
0.6535	Remote Similarity	NPC49051
0.6532	Remote Similarity	NPC478141
0.6524	Remote Similarity	NPC21449
0.6524	Remote Similarity	NPC157194
0.6524	Remote Similarity	NPC475683
0.6524	Remote Similarity	NPC474080
0.6524	Remote Similarity	NPC474102
0.6524	Remote Similarity	NPC474079
0.6509	Remote Similarity	NPC143325
0.6508	Remote Similarity	NPC224609
0.6508	Remote Similarity	NPC268063
0.6507	Remote Similarity	NPC477527
0.6491	Remote Similarity	NPC323752
0.6491	Remote Similarity	NPC323198
0.6486	Remote Similarity	NPC474069
0.648	Remote Similarity	NPC164006
0.6478	Remote Similarity	NPC313966
0.6478	Remote Similarity	NPC314254
0.6471	Remote Similarity	NPC474068
0.6471	Remote Similarity	NPC82436
0.6471	Remote Similarity	NPC474103
0.6471	Remote Similarity	NPC474064
0.6467	Remote Similarity	NPC471680
0.6465	Remote Similarity	NPC475024
0.6458	Remote Similarity	NPC231110
0.6455	Remote Similarity	NPC163147
0.6455	Remote Similarity	NPC252616
0.6455	Remote Similarity	NPC109498
0.6455	Remote Similarity	NPC32583
0.6455	Remote Similarity	NPC474090
0.6455	Remote Similarity	NPC45576
0.6455	Remote Similarity	NPC154873
0.6455	Remote Similarity	NPC61667
0.6444	Remote Similarity	NPC474070
0.6435	Remote Similarity	NPC478158
0.6429	Remote Similarity	NPC239762
0.6429	Remote Similarity	NPC476259
0.6429	Remote Similarity	NPC163392
0.6425	Remote Similarity	NPC312887
0.642	Remote Similarity	NPC475604
0.6419	Remote Similarity	NPC316403
0.6416	Remote Similarity	NPC186351
0.6406	Remote Similarity	NPC127775
0.6406	Remote Similarity	NPC474538
0.6402	Remote Similarity	NPC474067
0.6402	Remote Similarity	NPC185665
0.6402	Remote Similarity	NPC475737
0.6402	Remote Similarity	NPC474094
0.64	Remote Similarity	NPC132662
0.6398	Remote Similarity	NPC313421
0.6395	Remote Similarity	NPC200964
0.6393	Remote Similarity	NPC469426
0.6393	Remote Similarity	NPC469427
0.6385	Remote Similarity	NPC182507
0.6384	Remote Similarity	NPC473322
0.6382	Remote Similarity	NPC26108
0.6382	Remote Similarity	NPC469938
0.6382	Remote Similarity	NPC279871
0.6378	Remote Similarity	NPC473502
0.6378	Remote Similarity	NPC315266
0.6377	Remote Similarity	NPC473763
0.6377	Remote Similarity	NPC117244
0.6372	Remote Similarity	NPC319232
0.6372	Remote Similarity	NPC24370
0.6368	Remote Similarity	NPC206724
0.6368	Remote Similarity	NPC474515
0.6351	Remote Similarity	NPC49195
0.6351	Remote Similarity	NPC281049
0.6344	Remote Similarity	NPC34580
0.6344	Remote Similarity	NPC304307
0.6344	Remote Similarity	NPC118559
0.6344	Remote Similarity	NPC124920
0.6343	Remote Similarity	NPC475568
0.6337	Remote Similarity	NPC249662
0.6332	Remote Similarity	NPC137627
0.633	Remote Similarity	NPC13470
0.6328	Remote Similarity	NPC71933
0.6328	Remote Similarity	NPC105114
0.6328	Remote Similarity	NPC89923
0.6328	Remote Similarity	NPC239990
0.6328	Remote Similarity	NPC152850
0.6324	Remote Similarity	NPC471050
0.6324	Remote Similarity	NPC471049
0.6324	Remote Similarity	NPC471048
0.6321	Remote Similarity	NPC52587
0.6318	Remote Similarity	NPC313587
0.6318	Remote Similarity	NPC315893
0.6318	Remote Similarity	NPC54744
0.6318	Remote Similarity	NPC316110
0.6316	Remote Similarity	NPC100547
0.6302	Remote Similarity	NPC202591

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 NPC165538 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	140
0.1-0.2	437
0.2-0.3	836
0.3-0.4	1920
0.4-0.5	4149
0.5-0.6	1485
0.6-0.7	177
0.7-0.8	6
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
0.7906	Intermediate Similarity	NPD8339	Clinical (unspecified phase)
0.7592	Intermediate Similarity	NPD6632	Clinical (unspecified phase)
0.7513	Intermediate Similarity	NPD6348	Clinical (unspecified phase)
0.7371	Intermediate Similarity	NPD6349	Phase 1
0.7202	Intermediate Similarity	NPD7977	Clinical (unspecified phase)
0.7049	Intermediate Similarity	NPD5189	Clinical (unspecified phase)
0.6973	Remote Similarity	NPD5634	Approved
0.6959	Remote Similarity	NPD2957	Phase 2
0.6908	Remote Similarity	NPD6888	Discontinued
0.689	Remote Similarity	NPD8071	Approved
0.6821	Remote Similarity	NPD4125	Approved
0.6793	Remote Similarity	NPD5638	Approved
0.6782	Remote Similarity	NPD4949	Discontinued
0.6777	Remote Similarity	NPD8260	Approved
0.665	Remote Similarity	NPD6347	Phase 2
0.6649	Remote Similarity	NPD6915	Approved
0.6635	Remote Similarity	NPD7712	Clinical (unspecified phase)
0.6632	Remote Similarity	NPD4557	Approved
0.6631	Remote Similarity	NPD4648	Approved
0.6631	Remote Similarity	NPD4647	Approved
0.6631	Remote Similarity	NPD4646	Approved
0.663	Remote Similarity	NPD2022	Approved
0.6611	Remote Similarity	NPD3480	Approved
0.6593	Remote Similarity	NPD2437	Approved
0.6593	Remote Similarity	NPD2436	Approved
0.6592	Remote Similarity	NPD8172	Phase 2
0.6592	Remote Similarity	NPD8173	Phase 2
0.6591	Remote Similarity	NPD2043	Approved
0.6591	Remote Similarity	NPD2045	Approved
0.6591	Remote Similarity	NPD2051	Approved
0.6591	Remote Similarity	NPD2049	Clinical (unspecified phase)
0.6591	Remote Similarity	NPD2048	Approved
0.6591	Remote Similarity	NPD21	Approved
0.6591	Remote Similarity	NPD2047	Approved
0.6591	Remote Similarity	NPD2044	Approved
0.6591	Remote Similarity	NPD2046	Approved
0.6591	Remote Similarity	NPD2050	Clinical (unspecified phase)
0.6573	Remote Similarity	NPD5323	Approved
0.6567	Remote Similarity	NPD7483	Phase 2
0.6567	Remote Similarity	NPD7482	Phase 2
0.6559	Remote Similarity	NPD1004	Phase 2
0.6559	Remote Similarity	NPD1005	Phase 2
0.6557	Remote Similarity	NPD8272	Phase 2
0.654	Remote Similarity	NPD4134	Clinical (unspecified phase)
0.6538	Remote Similarity	NPD2087	Approved
0.6538	Remote Similarity	NPD2088	Approved
0.6538	Remote Similarity	NPD7490	Discontinued
0.6536	Remote Similarity	NPD7113	Clinical (unspecified phase)
0.6532	Remote Similarity	NPD8356	Approved
0.6524	Remote Similarity	NPD5230	Approved
0.6524	Remote Similarity	NPD5229	Approved
0.652	Remote Similarity	NPD2015	Discontinued
0.6518	Remote Similarity	NPD7711	Discontinued
0.6505	Remote Similarity	NPD7892	Clinical (unspecified phase)
0.6498	Remote Similarity	NPD7195	Clinical (unspecified phase)
0.6484	Remote Similarity	NPD7496	Phase 2
0.6474	Remote Similarity	NPD2891	Approved
0.6474	Remote Similarity	NPD2584	Suspended
0.6474	Remote Similarity	NPD2020	Approved
0.6468	Remote Similarity	NPD2852	Approved
0.6467	Remote Similarity	NPD5264	Approved
0.6467	Remote Similarity	NPD5265	Approved
0.6462	Remote Similarity	NPD4508	Discontinued
0.6461	Remote Similarity	NPD5299	Approved
0.6457	Remote Similarity	NPD2585	Clinical (unspecified phase)
0.6452	Remote Similarity	NPD1979	Approved
0.6432	Remote Similarity	NPD5298	Clinical (unspecified phase)
0.6429	Remote Similarity	NPD6916	Clinical (unspecified phase)
0.6425	Remote Similarity	NPD3561	Clinical (unspecified phase)
0.6421	Remote Similarity	NPD2019	Approved
0.6421	Remote Similarity	NPD2018	Approved
0.642	Remote Similarity	NPD5461	Discontinued
0.6417	Remote Similarity	NPD5614	Approved
0.6417	Remote Similarity	NPD3988	Approved
0.6417	Remote Similarity	NPD3987	Approved
0.6417	Remote Similarity	NPD5613	Approved
0.6416	Remote Similarity	NPD8430	Approved
0.6402	Remote Similarity	NPD6907	Phase 2
0.6398	Remote Similarity	NPD2054	Approved
0.6398	Remote Similarity	NPD2055	Phase 3
0.6398	Remote Similarity	NPD6857	Phase 3
0.6394	Remote Similarity	NPD6751	Clinical (unspecified phase)
0.6377	Remote Similarity	NPD5077	Approved
0.6377	Remote Similarity	NPD5076	Approved
0.6376	Remote Similarity	NPD4928	Approved
0.6376	Remote Similarity	NPD4930	Approved
0.6376	Remote Similarity	NPD3223	Clinical (unspecified phase)
0.6376	Remote Similarity	NPD4929	Approved
0.6373	Remote Similarity	NPD6092	Discontinued
0.6364	Remote Similarity	NPD5633	Discontinued
0.6364	Remote Similarity	NPD647	Approved
0.6359	Remote Similarity	NPD3335	Approved
0.6356	Remote Similarity	NPD6173	Approved
0.6346	Remote Similarity	NPD3288	Approved
0.6344	Remote Similarity	NPD1978	Approved
0.6341	Remote Similarity	NPD3334	Approved
0.6338	Remote Similarity	NPD7903	Clinical (unspecified phase)
0.633	Remote Similarity	NPD2016	Approved
0.633	Remote Similarity	NPD2013	Approved
0.633	Remote Similarity	NPD2014	Approved
0.6329	Remote Similarity	NPD3328	Phase 2
0.6328	Remote Similarity	NPD3608	Clinical (unspecified phase)
0.6318	Remote Similarity	NPD5755	Clinical (unspecified phase)
0.6313	Remote Similarity	NPD3351	Approved
0.6313	Remote Similarity	NPD4652	Approved
0.631	Remote Similarity	NPD6552	Clinical (unspecified phase)
0.6308	Remote Similarity	NPD7321	Clinical (unspecified phase)
0.6301	Remote Similarity	NPD3878	Approved
0.6298	Remote Similarity	NPD1977	Clinical (unspecified phase)
0.6298	Remote Similarity	NPD6659	Phase 2
0.6298	Remote Similarity	NPD8416	Discontinued
0.6296	Remote Similarity	NPD4432	Discontinued
0.6287	Remote Similarity	NPD7695	Clinical (unspecified phase)
0.6287	Remote Similarity	NPD6368	Clinical (unspecified phase)
0.6286	Remote Similarity	NPD7944	Discontinued
0.628	Remote Similarity	NPD5852	Approved
0.628	Remote Similarity	NPD4334	Discontinued
0.628	Remote Similarity	NPD5851	Approved
0.6276	Remote Similarity	NPD2098	Approved
0.6275	Remote Similarity	NPD1745	Approved
0.6273	Remote Similarity	NPD5452	Phase 2
0.6273	Remote Similarity	NPD3879	Approved
0.6271	Remote Similarity	NPD6495	Clinical (unspecified phase)
0.6269	Remote Similarity	NPD6910	Phase 3
0.6269	Remote Similarity	NPD7749	Clinical (unspecified phase)
0.6267	Remote Similarity	NPD3350	Approved
0.6263	Remote Similarity	NPD7613	Discontinued
0.6256	Remote Similarity	NPD4900	Clinical (unspecified phase)
0.6256	Remote Similarity	NPD2097	Approved
0.625	Remote Similarity	NPD8169	Discontinued
0.625	Remote Similarity	NPD4906	Approved
0.625	Remote Similarity	NPD4905	Approved
0.625	Remote Similarity	NPD4903	Approved
0.6244	Remote Similarity	NPD2416	Approved
0.6244	Remote Similarity	NPD2417	Approved
0.6233	Remote Similarity	NPD8271	Discontinued
0.6232	Remote Similarity	NPD6891	Phase 2
0.623	Remote Similarity	NPD5004	Approved
0.6224	Remote Similarity	NPD3487	Phase 1
0.6223	Remote Similarity	NPD8323	Discontinued
0.6221	Remote Similarity	NPD7289	Clinical (unspecified phase)
0.6221	Remote Similarity	NPD4904	Approved
0.622	Remote Similarity	NPD3785	Clinical (unspecified phase)
0.622	Remote Similarity	NPD5994	Discontinued
0.6216	Remote Similarity	NPD7970	Approved
0.6216	Remote Similarity	NPD7971	Clinical (unspecified phase)
0.6214	Remote Similarity	NPD8255	Phase 2
0.6213	Remote Similarity	NPD2893	Phase 3
0.6212	Remote Similarity	NPD4174	Clinical (unspecified phase)
0.6209	Remote Similarity	NPD4602	Approved
0.6207	Remote Similarity	NPD5485	Approved
0.6207	Remote Similarity	NPD5484	Approved
0.6205	Remote Similarity	NPD7599	Phase 2
0.6204	Remote Similarity	NPD8072	Approved
0.6202	Remote Similarity	NPD2856	Approved
0.6202	Remote Similarity	NPD2855	Approved
0.6202	Remote Similarity	NPD2854	Approved
0.6196	Remote Similarity	NPD6852	Discontinued
0.6196	Remote Similarity	NPD4126	Approved
0.6194	Remote Similarity	NPD4884	Discovery
0.6193	Remote Similarity	NPD4415	Approved
0.619	Remote Similarity	NPD6665	Discontinued
0.6186	Remote Similarity	NPD7817	Phase 1
0.6186	Remote Similarity	NPD7727	Phase 2
0.6181	Remote Similarity	NPD6304	Approved
0.6181	Remote Similarity	NPD6627	Discontinued
0.6181	Remote Similarity	NPD6303	Approved
0.618	Remote Similarity	NPD7807	Clinical (unspecified phase)
0.6175	Remote Similarity	NPD8643	Discontinued
0.6173	Remote Similarity	NPD7600	Phase 2
0.6172	Remote Similarity	NPD5112	Approved
0.6172	Remote Similarity	NPD5113	Approved
0.6172	Remote Similarity	NPD5114	Approved
0.6169	Remote Similarity	NPD7965	Phase 2
0.6169	Remote Similarity	NPD7964	Clinical (unspecified phase)
0.6164	Remote Similarity	NPD4960	Approved
0.6164	Remote Similarity	NPD4959	Approved
0.6157	Remote Similarity	NPD8107	Approved
0.6154	Remote Similarity	NPD8103	Clinical (unspecified phase)
0.615	Remote Similarity	NPD6119	Clinical (unspecified phase)
0.6142	Remote Similarity	NPD8108	Approved
0.6142	Remote Similarity	NPD3494	Approved
0.6142	Remote Similarity	NPD3492	Approved
0.6142	Remote Similarity	NPD3493	Approved
0.6141	Remote Similarity	NPD6475	Phase 2
0.6133	Remote Similarity	NPD3759	Clinical (unspecified phase)
0.6125	Remote Similarity	NPD6205	Discontinued
0.6124	Remote Similarity	NPD5367	Discontinued
0.6122	Remote Similarity	NPD4567	Approved
0.6122	Remote Similarity	NPD4566	Approved
0.6121	Remote Similarity	NPD7806	Phase 2
0.612	Remote Similarity	NPD4153	Approved
0.6117	Remote Similarity	NPD6860	Clinical (unspecified phase)
0.6114	Remote Similarity	NPD4315	Phase 2
0.6111	Remote Similarity	NPD4177	Approved
0.6111	Remote Similarity	NPD3074	Discontinued
0.6111	Remote Similarity	NPD4175	Approved
0.6106	Remote Similarity	NPD5444	Phase 1
0.6104	Remote Similarity	NPD8284	Discontinued
0.6103	Remote Similarity	NPD6911	Discontinued

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