NPASS Compound

Structure

NPC25316 OpenBabel07101718322D 53 58 0 0 1 0 0 0 0 0999 V2000 5.1483 -4.6786 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0151 2.4000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2947 2.8349 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3582 -4.7682 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.6834 0.1623 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.6055 2.3086 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7234 -4.0639 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.6620 -3.9259 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4160 -1.0315 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2221 -1.7463 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8939 -0.5063 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5062 -1.9358 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1779 -0.6958 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2681 -1.6000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2605 -2.0675 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1773 0.4953 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7805 2.2481 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7669 -3.9706 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 5.0927 -0.2957 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.9486 1.7605 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.3497 -3.4811 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.9841 -1.4105 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3431 -1.1819 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 4.7589 -2.1628 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6949 0.5894 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2210 1.6041 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.1901 -3.2848 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 4.0374 1.2490 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.2382 -2.9960 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.2718 1.1700 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0928 -2.8332 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.6537 0.6366 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4745 -2.2371 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0627 1.6068 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1898 -3.2880 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0956 -1.1987 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3403 -0.4012 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2961 -0.0882 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 1.0324 -1.4529 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 4.3005 -1.4424 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 1.0280 -0.0987 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 1.9819 0.8614 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 3.3466 -2.4024 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 3.3361 0.8657 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 1.9924 -2.4067 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 1.1391 1.9176 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.1931 -3.5858 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.4063 0.7369 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.2821 -2.3017 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4613 1.9394 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.8255 -3.6270 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.4289 -1.5855 0.0000 S 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 S 0 0 0 0 0 0 0 0 0 0 0 0 1 8 1 0 0 0 0 2 17 1 0 0 0 0 3 17 1 0 0 0 0 8 18 1 0 0 0 0 9 10 2 0 0 0 0 9 11 1 0 0 0 0 10 12 1 0 0 0 0 11 13 2 0 0 0 0 12 22 2 0 0 0 0 13 22 1 0 0 0 0 14 22 1 0 0 0 0 15 24 2 0 0 0 0 15 52 1 0 0 0 0 16 25 2 0 0 0 0 16 53 1 0 0 0 0 18 4 1 6 0 0 0 19 5 1 6 0 0 0 19 36 1 0 0 0 0 19 38 1 0 0 0 0 20 6 1 6 0 0 0 20 28 1 0 0 0 0 20 50 1 0 0 0 0 21 7 1 6 0 0 0 21 29 1 0 0 0 0 21 51 1 0 0 0 0 23 14 1 6 0 0 0 23 37 1 0 0 0 0 23 39 1 0 0 0 0 24 31 1 0 0 0 0 24 40 1 0 0 0 0 25 30 1 0 0 0 0 25 41 1 0 0 0 0 26 17 1 1 0 0 0 26 34 1 0 0 0 0 26 42 1 0 0 0 0 27 18 1 1 0 0 0 27 35 1 0 0 0 0 27 43 1 0 0 0 0 28 32 1 1 0 0 0 28 44 1 0 0 0 0 29 33 1 1 0 0 0 29 45 1 0 0 0 0 30 42 2 3 0 0 0 30 46 1 0 0 0 0 31 43 2 3 0 0 0 31 47 1 0 0 0 0 32 38 2 3 0 0 0 32 48 1 0 0 0 0 33 39 2 3 0 0 0 33 49 1 0 0 0 0 34 44 2 0 0 0 0 34 50 1 0 0 0 0 35 45 2 0 0 0 0 35 51 1 0 0 0 0 36 40 2 0 0 0 0 36 52 1 0 0 0 0 37 41 2 0 0 0 0 37 53 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	762.3
Volume:	740.629
LogP:	4.47
LogD:	3.852
LogS:	-2.131
# Rotatable Bonds:	5
TPSA:	203.43
# H-Bond Aceptor:	14
# H-Bond Donor:	5
# Rings:	6
# Heavy Atoms:	16

MedChem Properties

QED Drug-Likeness Score:	0.14
Synthetic Accessibility Score:	7.718
Fsp3:	0.486
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:	-4.642
MDCK Permeability:	1.551350942463614e-05
Pgp-inhibitor:	0.98
Pgp-substrate:	0.999
Human Intestinal Absorption (HIA):	0.013
20% Bioavailability (F20%):	0.017
30% Bioavailability (F30%):	0.437

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.702
Plasma Protein Binding (PPB):	72.94281768798828%
Volume Distribution (VD):	1.258
Pgp-substrate:	16.386255264282227%

ADMET: Metabolism

CYP1A2-inhibitor:	0.06
CYP1A2-substrate:	0.037
CYP2C19-inhibitor:	0.084
CYP2C19-substrate:	0.065
CYP2C9-inhibitor:	0.107
CYP2C9-substrate:	0.028
CYP2D6-inhibitor:	0.005
CYP2D6-substrate:	0.028
CYP3A4-inhibitor:	0.053
CYP3A4-substrate:	0.92

ADMET: Excretion

Clearance (CL):	1.282
Half-life (T1/2):	0.077

ADMET: Toxicity

hERG Blockers:	0.021
Human Hepatotoxicity (H-HT):	1.0
Drug-inuced Liver Injury (DILI):	0.995
AMES Toxicity:	0.006
Rat Oral Acute Toxicity:	0.162
Maximum Recommended Daily Dose:	0.989
Skin Sensitization:	0.007
Carcinogencity:	0.014
Eye Corrosion:	0.003
Eye Irritation:	0.006
Respiratory Toxicity:	0.393

Download Data

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

Natural Product: NPC25316

Natural Product ID:	NPC25316
*Common Name:**	Patellamide C
IUPAC Name:	n.a.
Synonyms:	Patellamide C
Standard InCHIKey:	CFXBLGFMQUFLKS-FUEDQDKVSA-N
Standard InCHI:	InChI=1S/C37H46N8O6S2/c1-8-18(4)27-35-45-29(21(7)51-35)33(49)39-23(14-22-12-10-9-11-13-22)37-41-25(16-53-37)30(46)42-26(17(2)3)34-44-28(20(6)50-34)32(48)38-19(5)36-40-24(15-52-36)31(47)43-27/h9-13,15-21,23,26-29H,8,14H2,1-7H3,(H,38,48)(H,39,49)(H,42,46)(H,43,47)/t18-,19+,20+,21+,23+,26-,27-,28-,29-/m0/s1
SMILES:	CC[C@@H]([C@@H]1N=C(O)c2csc(n2)[C@@H](C)N=C(O)[C@H]2N=C(O[C@@H]2C)[C@@H](N=C(c2nc([C@H](N=C([C@H]3N=C1O[C@@H]3C)O)Cc1ccccc1)sc2)O)C(C)C)C
Synthetic Gene Cluster:	BGC0000475;
ChEMBL Identifier:	CHEMBL501924
PubChem CID:	9767970
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000264] Organic acids and derivatives [CHEMONTID:0000265] Carboxylic acids and derivatives [CHEMONTID:0000013] Amino acids, peptides, and analogues [CHEMONTID:0000348] Peptides [CHEMONTID:0001995] Cyclic peptides

*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
NPO4712	Lissoclinum patella	Species	Didemnidae	Eukaryota	n.a.	n.a.	n.a.	PMID[1593285]
NPO4712	Lissoclinum patella	Species	Didemnidae	Eukaryota	n.a.	n.a.	n.a.	PMID[2095371]
NPO4712	Lissoclinum patella	Species	Didemnidae	Eukaryota	n.a.	n.a.	n.a.	PMID[2809606]
NPO4712	Lissoclinum patella	Species	Didemnidae	Eukaryota	n.a.	n.a.	n.a.	PMID[7623037]
NPO4712	Lissoclinum patella	Species	Didemnidae	Eukaryota	n.a.	n.a.	n.a.	PMID[9868162]
NPO4712	Lissoclinum patella	Species	Didemnidae	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
IC50	3
Others	3

Activity Type	# Activity
Cell Line	4
NON-MOLECULAR	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT137	Cell Line	L1210	Mus musculus	IC50	=	2.0	ug.mL-1	PMID[547020]
NPT91	Cell Line	KB	Homo sapiens	IC50	=	6.0	ug.mL-1	PMID[547022]
NPT137	Cell Line	L1210	Mus musculus	Activity	=	260.0	Zone units	PMID[547022]
NPT730	Cell Line	MC-38	Mus musculus	Activity	=	170.0	Zone units	PMID[547022]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	12.0	nM	PMID[547021]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Activity	=	0.0	Zone units	PMID[547022]

☑ 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 NPC25316 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	241
0.1-0.2	2284
0.2-0.3	15275
0.3-0.4	18219
0.4-0.5	5248
0.5-0.6	1353
0.6-0.7	46
0.7-0.8	20
0.8-0.85	1
0.85-0.9	0
0.9-0.95	2
0.95-1	8

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC263485
1.0	High Similarity	NPC229160
0.9938	High Similarity	NPC475330
0.9876	High Similarity	NPC174652
0.9752	High Similarity	NPC161242
0.963	High Similarity	NPC475534
0.963	High Similarity	NPC476080
0.9259	High Similarity	NPC24990
0.9202	High Similarity	NPC476103
0.8022	Intermediate Similarity	NPC329961
0.8	Intermediate Similarity	NPC96016
0.7935	Intermediate Similarity	NPC165538
0.7923	Intermediate Similarity	NPC122427
0.7705	Intermediate Similarity	NPC49051
0.7688	Intermediate Similarity	NPC74917
0.764	Intermediate Similarity	NPC120917
0.7438	Intermediate Similarity	NPC89592
0.7337	Intermediate Similarity	NPC475350
0.7337	Intermediate Similarity	NPC145178
0.7337	Intermediate Similarity	NPC14877
0.7313	Intermediate Similarity	NPC251036
0.7219	Intermediate Similarity	NPC161143
0.7202	Intermediate Similarity	NPC239660
0.7202	Intermediate Similarity	NPC106235
0.7188	Intermediate Similarity	NPC51692
0.7188	Intermediate Similarity	NPC267605
0.7	Intermediate Similarity	NPC135558
0.6954	Remote Similarity	NPC319751
0.693	Remote Similarity	NPC469858
0.6875	Remote Similarity	NPC473398
0.6836	Remote Similarity	NPC119481
0.677	Remote Similarity	NPC214375
0.6743	Remote Similarity	NPC475196
0.6686	Remote Similarity	NPC469801
0.6667	Remote Similarity	NPC75498
0.661	Remote Similarity	NPC475390
0.6592	Remote Similarity	NPC283783
0.6542	Remote Similarity	NPC313966
0.6542	Remote Similarity	NPC314254
0.6495	Remote Similarity	NPC249662
0.6455	Remote Similarity	NPC475920
0.6449	Remote Similarity	NPC79386
0.6421	Remote Similarity	NPC101980
0.6421	Remote Similarity	NPC470146
0.6421	Remote Similarity	NPC97078
0.6407	Remote Similarity	NPC478030
0.6373	Remote Similarity	NPC326407
0.6373	Remote Similarity	NPC317362
0.6373	Remote Similarity	NPC317725
0.6373	Remote Similarity	NPC318930
0.6364	Remote Similarity	NPC89489
0.6316	Remote Similarity	NPC257511
0.631	Remote Similarity	NPC315252
0.6276	Remote Similarity	NPC75609
0.6276	Remote Similarity	NPC140284
0.6218	Remote Similarity	NPC164006
0.619	Remote Similarity	NPC237219
0.618	Remote Similarity	NPC103268
0.614	Remote Similarity	NPC475568
0.6127	Remote Similarity	NPC475604
0.6119	Remote Similarity	NPC49195
0.6108	Remote Similarity	NPC188104
0.6073	Remote Similarity	NPC522
0.6073	Remote Similarity	NPC56058
0.6067	Remote Similarity	NPC474070
0.6061	Remote Similarity	NPC132662
0.6033	Remote Similarity	NPC470824
0.6009	Remote Similarity	NPC314930
0.6009	Remote Similarity	NPC214827
0.5989	Remote Similarity	NPC474102
0.5989	Remote Similarity	NPC474080
0.5989	Remote Similarity	NPC21449
0.5989	Remote Similarity	NPC475683
0.5989	Remote Similarity	NPC474079
0.5989	Remote Similarity	NPC157194
0.5979	Remote Similarity	NPC268063
0.5979	Remote Similarity	NPC224609
0.5966	Remote Similarity	NPC300315
0.5961	Remote Similarity	NPC197881
0.5953	Remote Similarity	NPC315061
0.5946	Remote Similarity	NPC474069
0.5938	Remote Similarity	NPC315411
0.5938	Remote Similarity	NPC231110
0.5936	Remote Similarity	NPC7817
0.5936	Remote Similarity	NPC82436
0.5936	Remote Similarity	NPC474068
0.5936	Remote Similarity	NPC474064
0.5936	Remote Similarity	NPC475168
0.5936	Remote Similarity	NPC474103
0.5926	Remote Similarity	NPC474090
0.5926	Remote Similarity	NPC154873
0.5926	Remote Similarity	NPC109498
0.5926	Remote Similarity	NPC32583
0.5926	Remote Similarity	NPC163147
0.5926	Remote Similarity	NPC252616
0.5926	Remote Similarity	NPC45576
0.5926	Remote Similarity	NPC14101
0.5926	Remote Similarity	NPC475024
0.5926	Remote Similarity	NPC61667
0.5907	Remote Similarity	NPC312887
0.5902	Remote Similarity	NPC238242
0.589	Remote Similarity	NPC110602
0.589	Remote Similarity	NPC75726
0.589	Remote Similarity	NPC31385
0.5888	Remote Similarity	NPC138562
0.5885	Remote Similarity	NPC127775
0.5885	Remote Similarity	NPC474538
0.5873	Remote Similarity	NPC475737
0.5873	Remote Similarity	NPC474094
0.5873	Remote Similarity	NPC474067
0.5873	Remote Similarity	NPC185665
0.587	Remote Similarity	NPC476978
0.5849	Remote Similarity	NPC313421
0.5842	Remote Similarity	NPC474515
0.5842	Remote Similarity	NPC50274
0.5842	Remote Similarity	NPC164228
0.5842	Remote Similarity	NPC206724
0.5842	Remote Similarity	NPC470902
0.5841	Remote Similarity	NPC182507
0.5829	Remote Similarity	NPC105717
0.5812	Remote Similarity	NPC478029
0.5806	Remote Similarity	NPC190329
0.5806	Remote Similarity	NPC262077
0.5805	Remote Similarity	NPC46427
0.5803	Remote Similarity	NPC52587
0.58	Remote Similarity	NPC477462
0.5784	Remote Similarity	NPC163055
0.5781	Remote Similarity	NPC202591
0.5781	Remote Similarity	NPC212214
0.5778	Remote Similarity	NPC287401
0.5775	Remote Similarity	NPC18487
0.5775	Remote Similarity	NPC83790
0.5775	Remote Similarity	NPC128237
0.5771	Remote Similarity	NPC472122
0.5771	Remote Similarity	NPC24594
0.5767	Remote Similarity	NPC193761
0.5765	Remote Similarity	NPC476118
0.5758	Remote Similarity	NPC34319
0.5753	Remote Similarity	NPC316008
0.5753	Remote Similarity	NPC313867
0.5753	Remote Similarity	NPC478158
0.5753	Remote Similarity	NPC162860
0.5751	Remote Similarity	NPC21126
0.575	Remote Similarity	NPC134480
0.5749	Remote Similarity	NPC329731
0.5749	Remote Similarity	NPC4910
0.5747	Remote Similarity	NPC252878
0.5741	Remote Similarity	NPC143325
0.5736	Remote Similarity	NPC475554
0.5736	Remote Similarity	NPC473886
0.5729	Remote Similarity	NPC161108
0.5726	Remote Similarity	NPC478028
0.5722	Remote Similarity	NPC314358
0.5721	Remote Similarity	NPC46413
0.5721	Remote Similarity	NPC469938
0.5721	Remote Similarity	NPC473704
0.5721	Remote Similarity	NPC475506
0.5707	Remote Similarity	NPC286551
0.5699	Remote Similarity	NPC470507
0.5699	Remote Similarity	NPC315283
0.5699	Remote Similarity	NPC314388
0.5694	Remote Similarity	NPC155143
0.5686	Remote Similarity	NPC472105
0.5686	Remote Similarity	NPC187827
0.5685	Remote Similarity	NPC222391
0.5682	Remote Similarity	NPC223791
0.5682	Remote Similarity	NPC107077
0.568	Remote Similarity	NPC472294
0.5678	Remote Similarity	NPC256912
0.5668	Remote Similarity	NPC322878
0.5667	Remote Similarity	NPC130309
0.5665	Remote Similarity	NPC326575
0.5665	Remote Similarity	NPC248454
0.5665	Remote Similarity	NPC211997
0.5664	Remote Similarity	NPC313804
0.5664	Remote Similarity	NPC315804
0.5663	Remote Similarity	NPC110129
0.5663	Remote Similarity	NPC201014
0.5662	Remote Similarity	NPC54420
0.5662	Remote Similarity	NPC323927
0.566	Remote Similarity	NPC59827
0.566	Remote Similarity	NPC184933
0.5658	Remote Similarity	NPC253987
0.5654	Remote Similarity	NPC473640
0.5645	Remote Similarity	NPC161069
0.5641	Remote Similarity	NPC220852
0.5637	Remote Similarity	NPC141377
0.5632	Remote Similarity	NPC476990
0.5631	Remote Similarity	NPC472108
0.5631	Remote Similarity	NPC472110
0.5631	Remote Similarity	NPC472109
0.5631	Remote Similarity	NPC139291
0.5628	Remote Similarity	NPC100321
0.5625	Remote Similarity	NPC478157
0.5625	Remote Similarity	NPC148592
0.5622	Remote Similarity	NPC158129
0.5619	Remote Similarity	NPC477815
0.5618	Remote Similarity	NPC273714
0.5616	Remote Similarity	NPC134586
0.5616	Remote Similarity	NPC470900

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 NPC25316 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	152
0.1-0.2	567
0.2-0.3	964
0.3-0.4	2300
0.4-0.5	4274
0.5-0.6	856
0.6-0.7	33
0.7-0.8	4
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
0.7323	Intermediate Similarity	NPD8071	Approved
0.7312	Intermediate Similarity	NPD7977	Clinical (unspecified phase)
0.7286	Intermediate Similarity	NPD8260	Approved
0.7202	Intermediate Similarity	NPD8339	Clinical (unspecified phase)
0.6891	Remote Similarity	NPD6632	Clinical (unspecified phase)
0.6778	Remote Similarity	NPD5189	Clinical (unspecified phase)
0.6735	Remote Similarity	NPD6348	Clinical (unspecified phase)
0.6703	Remote Similarity	NPD5634	Approved
0.6697	Remote Similarity	NPD7806	Phase 2
0.6599	Remote Similarity	NPD6349	Phase 1
0.6359	Remote Similarity	NPD2957	Phase 2
0.635	Remote Similarity	NPD2015	Discontinued
0.6324	Remote Similarity	NPD3127	Clinical (unspecified phase)
0.629	Remote Similarity	NPD6915	Approved
0.6262	Remote Similarity	NPD3469	Phase 3
0.625	Remote Similarity	NPD5191	Clinical (unspecified phase)
0.6207	Remote Similarity	NPD4949	Discontinued
0.62	Remote Similarity	NPD6092	Discontinued
0.619	Remote Similarity	NPD6888	Discontinued
0.6168	Remote Similarity	NPD4741	Phase 3
0.6168	Remote Similarity	NPD4742	Phase 3
0.6162	Remote Similarity	NPD3576	Approved
0.6162	Remote Similarity	NPD3575	Approved
0.6143	Remote Similarity	NPD7540	Clinical (unspecified phase)
0.6138	Remote Similarity	NPD4670	Clinical (unspecified phase)
0.6138	Remote Similarity	NPD4669	Clinical (unspecified phase)
0.6138	Remote Similarity	NPD4671	Clinical (unspecified phase)
0.6122	Remote Similarity	NPD924	Discontinued
0.6116	Remote Similarity	NPD4856	Approved
0.6116	Remote Similarity	NPD4855	Phase 1
0.61	Remote Similarity	NPD1745	Approved
0.6091	Remote Similarity	NPD8284	Discontinued
0.6082	Remote Similarity	NPD5702	Clinical (unspecified phase)
0.6077	Remote Similarity	NPD5828	Phase 2
0.6068	Remote Similarity	NPD2717	Phase 2
0.6066	Remote Similarity	NPD6308	Phase 1
0.6066	Remote Similarity	NPD7321	Clinical (unspecified phase)
0.6045	Remote Similarity	NPD3759	Clinical (unspecified phase)
0.6034	Remote Similarity	NPD7816	Clinical (unspecified phase)
0.6033	Remote Similarity	NPD5502	Approved
0.6033	Remote Similarity	NPD5503	Approved
0.6029	Remote Similarity	NPD8110	Clinical (unspecified phase)
0.6027	Remote Similarity	NPD7496	Phase 2
0.602	Remote Similarity	NPD5596	Phase 2
0.6	Remote Similarity	NPD7711	Discontinued
0.5991	Remote Similarity	NPD3015	Discontinued
0.5991	Remote Similarity	NPD4134	Clinical (unspecified phase)
0.598	Remote Similarity	NPD5755	Clinical (unspecified phase)
0.5975	Remote Similarity	NPD6205	Discontinued
0.5963	Remote Similarity	NPD7195	Clinical (unspecified phase)
0.5949	Remote Similarity	NPD7133	Discontinued
0.5946	Remote Similarity	NPD649	Clinical (unspecified phase)
0.5946	Remote Similarity	NPD5595	Clinical (unspecified phase)
0.594	Remote Similarity	NPD7770	Phase 3
0.5939	Remote Similarity	NPD647	Approved
0.5939	Remote Similarity	NPD4929	Approved
0.5939	Remote Similarity	NPD4928	Approved
0.5939	Remote Similarity	NPD4930	Approved
0.5936	Remote Similarity	NPD1005	Phase 2
0.5936	Remote Similarity	NPD1004	Phase 2
0.5935	Remote Similarity	NPD8272	Phase 2
0.5933	Remote Similarity	NPD6347	Phase 2
0.5926	Remote Similarity	NPD7836	Clinical (unspecified phase)
0.592	Remote Similarity	NPD7104	Clinical (unspecified phase)
0.5918	Remote Similarity	NPD6916	Clinical (unspecified phase)
0.5888	Remote Similarity	NPD4650	Approved
0.5888	Remote Similarity	NPD6324	Phase 1
0.5873	Remote Similarity	NPD6907	Phase 2
0.5873	Remote Similarity	NPD3835	Phase 3
0.5873	Remote Similarity	NPD3833	Phase 3
0.5865	Remote Similarity	NPD7127	Clinical (unspecified phase)
0.5865	Remote Similarity	NPD5435	Phase 1
0.586	Remote Similarity	NPD3401	Clinical (unspecified phase)
0.5859	Remote Similarity	NPD754	Clinical (unspecified phase)
0.5858	Remote Similarity	NPD7769	Phase 3
0.5855	Remote Similarity	NPD704	Clinical (unspecified phase)
0.5845	Remote Similarity	NPD8063	Discontinued
0.5842	Remote Similarity	NPD8464	Clinical (unspecified phase)
0.584	Remote Similarity	NPD3328	Phase 2
0.5838	Remote Similarity	NPD3834	Clinical (unspecified phase)
0.5829	Remote Similarity	NPD1219	Approved
0.5829	Remote Similarity	NPD1218	Approved
0.5829	Remote Similarity	NPD7490	Discontinued
0.5825	Remote Similarity	NPD7494	Clinical (unspecified phase)
0.5824	Remote Similarity	NPD6360	Discontinued
0.5822	Remote Similarity	NPD4599	Clinical (unspecified phase)
0.5818	Remote Similarity	NPD5452	Phase 2
0.5813	Remote Similarity	NPD8408	Discontinued
0.5813	Remote Similarity	NPD5461	Discontinued
0.5806	Remote Similarity	NPD8322	Phase 2
0.5805	Remote Similarity	NPD5438	Approved
0.5805	Remote Similarity	NPD5439	Approved
0.58	Remote Similarity	NPD1260	Approved
0.5794	Remote Similarity	NPD8061	Clinical (unspecified phase)
0.5781	Remote Similarity	NPD1597	Phase 1
0.5775	Remote Similarity	NPD4509	Discontinued
0.5773	Remote Similarity	NPD4557	Approved
0.5767	Remote Similarity	NPD5023	Discontinued
0.5765	Remote Similarity	NPD5140	Approved
0.5765	Remote Similarity	NPD5138	Approved
0.5765	Remote Similarity	NPD3907	Clinical (unspecified phase)
0.576	Remote Similarity	NPD7001	Phase 3
0.5756	Remote Similarity	NPD5047	Clinical (unspecified phase)
0.5751	Remote Similarity	NPD6910	Phase 3
0.5749	Remote Similarity	NPD2749	Discontinued
0.5741	Remote Similarity	NPD8072	Approved
0.5741	Remote Similarity	NPD5144	Discontinued
0.574	Remote Similarity	NPD2543	Discontinued
0.5735	Remote Similarity	NPD3396	Approved
0.5735	Remote Similarity	NPD3395	Approved
0.5721	Remote Similarity	NPD4331	Approved
0.5721	Remote Similarity	NPD2152	Clinical (unspecified phase)
0.5721	Remote Similarity	NPD1881	Approved
0.572	Remote Similarity	NPD2893	Phase 3
0.5714	Remote Similarity	NPD3487	Phase 1
0.5714	Remote Similarity	NPD6368	Clinical (unspecified phase)
0.5708	Remote Similarity	NPD6717	Clinical (unspecified phase)
0.5708	Remote Similarity	NPD7981	Discontinued
0.5703	Remote Similarity	NPD8107	Approved
0.5701	Remote Similarity	NPD6137	Clinical (unspecified phase)
0.5699	Remote Similarity	NPD6119	Clinical (unspecified phase)
0.5698	Remote Similarity	NPD7928	Approved
0.5698	Remote Similarity	NPD7929	Approved
0.5696	Remote Similarity	NPD6170	Phase 2
0.569	Remote Similarity	NPD9579	Approved
0.5688	Remote Similarity	NPD7289	Clinical (unspecified phase)
0.5687	Remote Similarity	NPD6751	Clinical (unspecified phase)
0.5686	Remote Similarity	NPD8108	Approved
0.5685	Remote Similarity	NPD8129	Discovery
0.5683	Remote Similarity	NPD6381	Phase 2
0.5681	Remote Similarity	NPD7021	Clinical (unspecified phase)
0.568	Remote Similarity	NPD7483	Phase 2
0.568	Remote Similarity	NPD7482	Phase 2
0.5677	Remote Similarity	NPD5663	Discontinued
0.567	Remote Similarity	NPD6911	Discontinued
0.5668	Remote Similarity	NPD6139	Clinical (unspecified phase)
0.5667	Remote Similarity	NPD5817	Discontinued
0.5665	Remote Similarity	NPD8123	Approved
0.5665	Remote Similarity	NPD8122	Approved
0.5664	Remote Similarity	NPD6455	Phase 3
0.5663	Remote Similarity	NPD7737	Approved
0.5663	Remote Similarity	NPD7738	Approved
0.5662	Remote Similarity	NPD7834	Approved
0.5659	Remote Similarity	NPD5323	Approved
0.5657	Remote Similarity	NPD2389	Approved
0.5656	Remote Similarity	NPD3843	Clinical (unspecified phase)
0.5654	Remote Similarity	NPD7946	Pre-registration
0.5652	Remote Similarity	NPD6227	Discontinued
0.565	Remote Similarity	NPD5367	Discontinued
0.5644	Remote Similarity	NPD5523	Approved
0.5644	Remote Similarity	NPD1976	Approved
0.5644	Remote Similarity	NPD5524	Approved
0.5642	Remote Similarity	NPD7712	Clinical (unspecified phase)
0.5638	Remote Similarity	NPD3525	Discontinued
0.5635	Remote Similarity	NPD3492	Approved
0.5635	Remote Similarity	NPD3494	Approved
0.5635	Remote Similarity	NPD3493	Approved
0.5628	Remote Similarity	NPD6977	Clinical (unspecified phase)
0.5628	Remote Similarity	NPD6978	Phase 2
0.5625	Remote Similarity	NPD6819	Phase 2
0.5625	Remote Similarity	NPD3848	Phase 2
0.5625	Remote Similarity	NPD4273	Approved
0.5622	Remote Similarity	NPD1897	Discontinued
0.5622	Remote Similarity	NPD8073	Approved
0.5619	Remote Similarity	NPD3474	Discovery
0.5616	Remote Similarity	NPD8403	Phase 1
0.5614	Remote Similarity	NPD7399	Clinical (unspecified phase)
0.5609	Remote Similarity	NPD6246	Approved
0.5609	Remote Similarity	NPD6976	Clinical (unspecified phase)
0.5604	Remote Similarity	NPD2306	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