NPASS Compound

Structure

NPC17698 OpenBabel07101718202D 53 56 0 0 1 0 0 0 0 0999 V2000 0.5616 8.2708 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6332 7.2734 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3380 8.7075 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4024 4.8094 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4013 -0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1948 6.7127 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1660 8.1468 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1998 3.8302 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6092 0.1691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.8949 4.4934 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0042 3.0080 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.6240 3.0943 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.7525 3.9792 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.8618 2.4937 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.6350 2.0943 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3517 5.1237 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4067 -0.9135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1631 4.5221 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9224 6.5887 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8842 -0.2070 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1957 -2.0376 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0944 7.1494 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0207 4.0078 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2889 4.0365 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -7.7360 2.9793 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2505 3.5159 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.8508 5.5912 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.9176 -0.4632 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.7431 0.6691 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.3208 1.1450 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7843 4.4006 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8229 5.3565 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2288 1.5433 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0561 5.0859 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9201 -0.3916 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5036 6.4172 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2504 5.7522 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 4.7061 7.3965 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 3.5542 6.1030 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -3.7153 0.3491 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -2.0111 -1.4588 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -3.6660 4.8188 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 1.4042 2.5278 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -0.8552 5.4977 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -1.2893 -3.0332 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.5936 2.4651 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.2054 0.6788 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.5801 5.0061 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.2145 6.2766 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.1709 1.2082 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.6122 5.9170 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.6854 -1.3636 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 2 2 0 0 0 0 1 3 1 0 0 0 0 2 6 1 0 0 0 0 3 7 2 0 0 0 0 4 8 1 0 0 0 0 4 16 1 0 0 0 0 5 9 1 0 0 0 0 5 17 1 0 0 0 0 6 22 2 0 0 0 0 7 22 1 0 0 0 0 10 13 1 0 0 0 0 10 23 2 0 0 0 0 11 14 2 0 0 0 0 11 23 1 0 0 0 0 12 15 2 0 0 0 0 12 24 1 0 0 0 0 13 25 2 0 0 0 0 14 25 1 0 0 0 0 15 30 1 0 0 0 0 16 39 1 0 0 0 0 17 45 1 0 0 0 0 18 23 1 0 0 0 0 19 22 1 0 0 0 0 20 28 1 0 0 0 0 20 40 1 0 0 0 0 21 41 2 3 0 0 0 21 46 1 0 0 0 0 24 18 1 6 0 0 0 24 42 1 0 0 0 0 25 47 1 0 0 0 0 26 8 1 6 0 0 0 26 31 1 0 0 0 0 26 43 1 0 0 0 0 27 19 1 1 0 0 0 27 32 1 0 0 0 0 27 44 1 0 0 0 0 28 35 1 0 0 0 0 28 41 1 1 0 0 0 29 9 1 6 0 0 0 29 33 1 0 0 0 0 29 45 1 0 0 0 0 30 40 2 3 0 0 0 30 48 1 0 0 0 0 31 34 1 0 0 0 0 31 49 2 0 0 0 0 32 42 2 3 0 0 0 32 50 1 0 0 0 0 33 43 2 3 0 0 0 33 51 1 0 0 0 0 34 44 1 0 0 0 0 34 52 2 0 0 0 0 35 45 1 0 0 0 0 35 53 2 0 0 0 0 36 37 2 0 0 0 0 36 38 1 0 0 0 0 36 39 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	731.34
Volume:	726.732
LogP:	-0.722
LogD:	0.062
LogS:	-3.826
# Rotatable Bonds:	11
TPSA:	265.01
# H-Bond Aceptor:	17
# H-Bond Donor:	10
# Rings:	4
# Heavy Atoms:	17

MedChem Properties

QED Drug-Likeness Score:	0.044
Synthetic Accessibility Score:	5.297
Fsp3:	0.389
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:	-6.404
MDCK Permeability:	1.1427167009969708e-05
Pgp-inhibitor:	0.001
Pgp-substrate:	0.994
Human Intestinal Absorption (HIA):	0.975
20% Bioavailability (F20%):	1.0
30% Bioavailability (F30%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.073
Plasma Protein Binding (PPB):	47.157718658447266%
Volume Distribution (VD):	0.272
Pgp-substrate:	53.62807083129883%

ADMET: Metabolism

CYP1A2-inhibitor:	0.001
CYP1A2-substrate:	0.009
CYP2C19-inhibitor:	0.136
CYP2C19-substrate:	0.037
CYP2C9-inhibitor:	0.368
CYP2C9-substrate:	0.089
CYP2D6-inhibitor:	0.012
CYP2D6-substrate:	0.234
CYP3A4-inhibitor:	0.181
CYP3A4-substrate:	0.015

ADMET: Excretion

Clearance (CL):	2.374
Half-life (T1/2):	0.556

ADMET: Toxicity

hERG Blockers:	0.122
Human Hepatotoxicity (H-HT):	0.123
Drug-inuced Liver Injury (DILI):	0.241
AMES Toxicity:	0.065
Rat Oral Acute Toxicity:	0.36
Maximum Recommended Daily Dose:	0.97
Skin Sensitization:	0.232
Carcinogencity:	0.199
Eye Corrosion:	0.003
Eye Irritation:	0.004
Respiratory Toxicity:	0.887

Download Data

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

Natural Product: NPC17698

Natural Product ID:	NPC17698
*Common Name:**	Cyclotheonamide A
IUPAC Name:	N-[(3S,7E,9S,12R,16S,19S)-12-benzyl-16-[3-(diaminomethylideneamino)propyl]-9-[(4-hydroxyphenyl)methyl]-2,6,11,14,15,18-hexaoxo-1,5,10,13,17-pentazabicyclo[17.3.0]docos-7-en-3-yl]formamide
Synonyms:
Standard InCHIKey:	CDWXSPKJKIUEQF-BIXWYCRZSA-N
Standard InCHI:	InChI=1S/C36H45N9O8/c37-36(38)39-16-4-8-26-31(49)34(52)44-27(19-22-6-2-1-3-7-22)32(50)42-24(18-23-10-13-25(47)14-11-23)12-15-30(48)40-20-28(41-21-46)35(53)45-17-5-9-29(45)33(51)43-26/h1-3,6-7,10-15,21,24,26-29,47H,4-5,8-9,16-20H2,(H,40,48)(H,41,46)(H,42,50)(H,43,51)(H,44,52)(H4,37,38,39)/b15-12+/t24-,26+,27-,28+,29+/m1/s1
SMILES:	c1ccc(cc1)C[C@@H]1C(=N[C@H](/C=C/C(=NC[C@@H](C(=O)N2CCC[C@H]2C(=N[C@@H](CCCNC(=N)N)C(=O)C(=O)N1)O)N=CO)O)Cc1ccc(cc1)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL342672
PubChem CID:	5287991
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
NPO33174	theonella	Genus	Theonellidae	Eukaryota	n.a.	n.a.	n.a.	PMID[9599274]

☑ 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
Ki	2

Activity Type	# Activity
Individual Protein	4
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT670	Individual Protein	Thrombin	Homo sapiens	Ki	=	1.0	nM	PMID[549780]
NPT670	Individual Protein	Thrombin	Homo sapiens	IC50	=	23.0	nM	PMID[549781]
NPT2	Others	Unspecified		IC50	=	16.0	nM	PMID[549781]
NPT670	Individual Protein	Thrombin	Homo sapiens	IC50	=	1500.0	nM	PMID[549782]
NPT670	Individual Protein	Thrombin	Homo sapiens	Ki	=	180.0	nM	PMID[549783]

☑ 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 NPC17698 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	259
0.1-0.2	1650
0.2-0.3	11052
0.3-0.4	7004
0.4-0.5	17960
0.5-0.6	3855
0.6-0.7	660
0.7-0.8	210
0.8-0.85	33
0.85-0.9	9
0.9-0.95	2
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9684	High Similarity	NPC475532
0.9623	High Similarity	NPC165285
0.9494	High Similarity	NPC129486
0.8841	High Similarity	NPC274198
0.8841	High Similarity	NPC198254
0.878	High Similarity	NPC280022
0.8727	High Similarity	NPC276506
0.8639	High Similarity	NPC119652
0.8639	High Similarity	NPC97526
0.8631	High Similarity	NPC196243
0.848	Intermediate Similarity	NPC153554
0.8415	Intermediate Similarity	NPC469243
0.8409	Intermediate Similarity	NPC61332
0.8409	Intermediate Similarity	NPC240130
0.8324	Intermediate Similarity	NPC473404
0.8303	Intermediate Similarity	NPC475544
0.8302	Intermediate Similarity	NPC16188
0.8295	Intermediate Similarity	NPC94862
0.8272	Intermediate Similarity	NPC202198
0.8263	Intermediate Similarity	NPC63931
0.8263	Intermediate Similarity	NPC223207
0.8242	Intermediate Similarity	NPC244336
0.8214	Intermediate Similarity	NPC304074
0.8214	Intermediate Similarity	NPC471771
0.8214	Intermediate Similarity	NPC290755
0.821	Intermediate Similarity	NPC233702
0.8171	Intermediate Similarity	NPC473580
0.8167	Intermediate Similarity	NPC302715
0.8166	Intermediate Similarity	NPC328649
0.816	Intermediate Similarity	NPC262166
0.8148	Intermediate Similarity	NPC473491
0.8144	Intermediate Similarity	NPC241794
0.8122	Intermediate Similarity	NPC477638
0.8122	Intermediate Similarity	NPC477632
0.8107	Intermediate Similarity	NPC61004
0.8101	Intermediate Similarity	NPC476989
0.8061	Intermediate Similarity	NPC244509
0.8059	Intermediate Similarity	NPC302597
0.8057	Intermediate Similarity	NPC475409
0.8057	Intermediate Similarity	NPC170302
0.8057	Intermediate Similarity	NPC475564
0.8049	Intermediate Similarity	NPC5194
0.8049	Intermediate Similarity	NPC56685
0.8049	Intermediate Similarity	NPC261934
0.8046	Intermediate Similarity	NPC473546
0.8045	Intermediate Similarity	NPC102959
0.8038	Intermediate Similarity	NPC214988
0.8013	Intermediate Similarity	NPC267237
0.8	Intermediate Similarity	NPC60516
0.7978	Intermediate Similarity	NPC329295
0.7977	Intermediate Similarity	NPC137627
0.7965	Intermediate Similarity	NPC475123
0.7965	Intermediate Similarity	NPC475204
0.7963	Intermediate Similarity	NPC311658
0.7953	Intermediate Similarity	NPC141957
0.7931	Intermediate Similarity	NPC26108
0.7925	Intermediate Similarity	NPC48202
0.7901	Intermediate Similarity	NPC477636
0.7889	Intermediate Similarity	NPC96275
0.7874	Intermediate Similarity	NPC306804
0.7862	Intermediate Similarity	NPC242159
0.7862	Intermediate Similarity	NPC313694
0.7861	Intermediate Similarity	NPC46009
0.7857	Intermediate Similarity	NPC323336
0.7857	Intermediate Similarity	NPC326349
0.7844	Intermediate Similarity	NPC476268
0.7829	Intermediate Similarity	NPC471165
0.7814	Intermediate Similarity	NPC477631
0.7803	Intermediate Similarity	NPC66490
0.7802	Intermediate Similarity	NPC51047
0.7797	Intermediate Similarity	NPC194671
0.7797	Intermediate Similarity	NPC269750
0.7784	Intermediate Similarity	NPC477639
0.7751	Intermediate Similarity	NPC324850
0.7727	Intermediate Similarity	NPC279871
0.7727	Intermediate Similarity	NPC136797
0.7714	Intermediate Similarity	NPC89831
0.7701	Intermediate Similarity	NPC477552
0.7701	Intermediate Similarity	NPC477550
0.7684	Intermediate Similarity	NPC50016
0.767	Intermediate Similarity	NPC273755
0.7657	Intermediate Similarity	NPC40234
0.765	Intermediate Similarity	NPC246591
0.7644	Intermediate Similarity	NPC294516
0.7644	Intermediate Similarity	NPC107938
0.7627	Intermediate Similarity	NPC476227
0.7619	Intermediate Similarity	NPC469443
0.7619	Intermediate Similarity	NPC477551
0.7617	Intermediate Similarity	NPC478005
0.7614	Intermediate Similarity	NPC230611
0.7607	Intermediate Similarity	NPC168861
0.7598	Intermediate Similarity	NPC45037
0.7568	Intermediate Similarity	NPC470728
0.754	Intermediate Similarity	NPC80514
0.7528	Intermediate Similarity	NPC473402
0.7528	Intermediate Similarity	NPC155506
0.7528	Intermediate Similarity	NPC159767
0.7514	Intermediate Similarity	NPC328494
0.75	Intermediate Similarity	NPC287757
0.75	Intermediate Similarity	NPC319320
0.7472	Intermediate Similarity	NPC248670
0.7432	Intermediate Similarity	NPC294951
0.743	Intermediate Similarity	NPC473354
0.7418	Intermediate Similarity	NPC477637
0.7396	Intermediate Similarity	NPC324081
0.7391	Intermediate Similarity	NPC299806
0.7385	Intermediate Similarity	NPC220060
0.7376	Intermediate Similarity	NPC478007
0.7356	Intermediate Similarity	NPC114806
0.7347	Intermediate Similarity	NPC469444
0.7333	Intermediate Similarity	NPC158277
0.7329	Intermediate Similarity	NPC257390
0.7329	Intermediate Similarity	NPC326966
0.7317	Intermediate Similarity	NPC132636
0.7312	Intermediate Similarity	NPC325651
0.7304	Intermediate Similarity	NPC478008
0.7299	Intermediate Similarity	NPC1390
0.7299	Intermediate Similarity	NPC24617
0.7299	Intermediate Similarity	NPC62104
0.7288	Intermediate Similarity	NPC254700
0.7273	Intermediate Similarity	NPC191863
0.7273	Intermediate Similarity	NPC289776
0.7273	Intermediate Similarity	NPC133470
0.7254	Intermediate Similarity	NPC473450
0.7251	Intermediate Similarity	NPC300443
0.7247	Intermediate Similarity	NPC209463
0.7246	Intermediate Similarity	NPC326241
0.7243	Intermediate Similarity	NPC471049
0.7243	Intermediate Similarity	NPC471050
0.7243	Intermediate Similarity	NPC471048
0.7236	Intermediate Similarity	NPC469445
0.7234	Intermediate Similarity	NPC163961
0.7234	Intermediate Similarity	NPC473305
0.7232	Intermediate Similarity	NPC472923
0.7228	Intermediate Similarity	NPC476321
0.7208	Intermediate Similarity	NPC194699
0.7208	Intermediate Similarity	NPC219350
0.7204	Intermediate Similarity	NPC235194
0.7204	Intermediate Similarity	NPC138083
0.7189	Intermediate Similarity	NPC471526
0.7174	Intermediate Similarity	NPC32064
0.7163	Intermediate Similarity	NPC323244
0.716	Intermediate Similarity	NPC81026
0.716	Intermediate Similarity	NPC255447
0.7143	Intermediate Similarity	NPC164608
0.7135	Intermediate Similarity	NPC210377
0.7135	Intermediate Similarity	NPC5719
0.7135	Intermediate Similarity	NPC22883
0.7135	Intermediate Similarity	NPC217804
0.712	Intermediate Similarity	NPC475421
0.711	Intermediate Similarity	NPC122590
0.7109	Intermediate Similarity	NPC328924
0.7107	Intermediate Similarity	NPC81845
0.7101	Intermediate Similarity	NPC266741
0.7093	Intermediate Similarity	NPC7817
0.7093	Intermediate Similarity	NPC475168
0.7074	Intermediate Similarity	NPC276120
0.7069	Intermediate Similarity	NPC39431
0.7065	Intermediate Similarity	NPC469442
0.7065	Intermediate Similarity	NPC277306
0.7056	Intermediate Similarity	NPC63040
0.7055	Intermediate Similarity	NPC130309
0.7048	Intermediate Similarity	NPC109580
0.7037	Intermediate Similarity	NPC473322
0.7031	Intermediate Similarity	NPC328763
0.7029	Intermediate Similarity	NPC469903
0.7025	Intermediate Similarity	NPC71684
0.7021	Intermediate Similarity	NPC315542
0.7018	Intermediate Similarity	NPC119569
0.7017	Intermediate Similarity	NPC186617
0.7016	Intermediate Similarity	NPC248822
0.7015	Intermediate Similarity	NPC295795
0.7005	Intermediate Similarity	NPC167763
0.7005	Intermediate Similarity	NPC470903
0.7005	Intermediate Similarity	NPC470112
0.7	Intermediate Similarity	NPC15068
0.6995	Remote Similarity	NPC59827
0.6995	Remote Similarity	NPC184933
0.6995	Remote Similarity	NPC25539
0.6978	Remote Similarity	NPC471568
0.6978	Remote Similarity	NPC473693
0.6977	Remote Similarity	NPC9373
0.6971	Remote Similarity	NPC470902
0.6971	Remote Similarity	NPC473002
0.697	Remote Similarity	NPC244866
0.6966	Remote Similarity	NPC469902
0.6966	Remote Similarity	NPC473003
0.6963	Remote Similarity	NPC64140
0.6963	Remote Similarity	NPC174122
0.6963	Remote Similarity	NPC283207
0.6959	Remote Similarity	NPC473804
0.6959	Remote Similarity	NPC314358
0.6947	Remote Similarity	NPC329731
0.6943	Remote Similarity	NPC65714
0.6941	Remote Similarity	NPC315283
0.6941	Remote Similarity	NPC314388
0.6937	Remote Similarity	NPC6975
0.6936	Remote Similarity	NPC2501
0.6933	Remote Similarity	NPC111428
0.6928	Remote Similarity	NPC141050

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 NPC17698 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	157
0.1-0.2	442
0.2-0.3	745
0.3-0.4	1436
0.4-0.5	3721
0.5-0.6	2336
0.6-0.7	280
0.7-0.8	30
0.8-0.85	2
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8773	High Similarity	NPD8303	Discontinued
0.8202	Intermediate Similarity	NPD7617	Discontinued
0.8182	Intermediate Similarity	NPD7118	Clinical (unspecified phase)
0.8133	Intermediate Similarity	NPD8019	Approved
0.8035	Intermediate Similarity	NPD5200	Clinical (unspecified phase)
0.8024	Intermediate Similarity	NPD7495	Discontinued
0.7939	Intermediate Similarity	NPD7523	Phase 3
0.7697	Intermediate Similarity	NPD8290	Clinical (unspecified phase)
0.7578	Intermediate Similarity	NPD4782	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD6809	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD8076	Discontinued
0.7471	Intermediate Similarity	NPD6670	Clinical (unspecified phase)
0.747	Intermediate Similarity	NPD7066	Clinical (unspecified phase)
0.7456	Intermediate Similarity	NPD7303	Discontinued
0.7456	Intermediate Similarity	NPD6078	Clinical (unspecified phase)
0.7453	Intermediate Similarity	NPD4791	Clinical (unspecified phase)
0.7439	Intermediate Similarity	NPD7450	Phase 2
0.7416	Intermediate Similarity	NPD5137	Approved
0.736	Intermediate Similarity	NPD4652	Approved
0.733	Intermediate Similarity	NPD2098	Approved
0.7329	Intermediate Similarity	NPD3632	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD7728	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD1330	Phase 2
0.7222	Intermediate Similarity	NPD1329	Clinical (unspecified phase)
0.7216	Intermediate Similarity	NPD2097	Approved
0.7212	Intermediate Similarity	NPD6901	Phase 3
0.7209	Intermediate Similarity	NPD7131	Phase 3
0.7207	Intermediate Similarity	NPD7484	Phase 3
0.7207	Intermediate Similarity	NPD7485	Phase 3
0.7195	Intermediate Similarity	NPD4757	Clinical (unspecified phase)
0.7193	Intermediate Similarity	NPD5348	Clinical (unspecified phase)
0.7188	Intermediate Similarity	NPD5339	Clinical (unspecified phase)
0.7151	Intermediate Similarity	NPD7613	Discontinued
0.7143	Intermediate Similarity	NPD5341	Clinical (unspecified phase)
0.7112	Intermediate Similarity	NPD5946	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD7978	Discontinued
0.7081	Intermediate Similarity	NPD8292	Phase 2
0.7055	Intermediate Similarity	NPD3136	Phase 2
0.7027	Intermediate Similarity	NPD7695	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD6860	Clinical (unspecified phase)
0.6964	Remote Similarity	NPD6867	Clinical (unspecified phase)
0.6964	Remote Similarity	NPD6866	Clinical (unspecified phase)
0.6941	Remote Similarity	NPD6681	Discovery
0.6931	Remote Similarity	NPD6557	Phase 2
0.6923	Remote Similarity	NPD2888	Approved
0.6923	Remote Similarity	NPD2017	Approved
0.6923	Remote Similarity	NPD2890	Approved
0.6923	Remote Similarity	NPD2889	Approved
0.6919	Remote Similarity	NPD8022	Clinical (unspecified phase)
0.6871	Remote Similarity	NPD7451	Discontinued
0.6851	Remote Similarity	NPD8031	Discontinued
0.6839	Remote Similarity	NPD6682	Clinical (unspecified phase)
0.6833	Remote Similarity	NPD5967	Approved
0.6832	Remote Similarity	NPD2562	Approved
0.6832	Remote Similarity	NPD2561	Approved
0.6829	Remote Similarity	NPD6189	Approved
0.6829	Remote Similarity	NPD6188	Approved
0.6805	Remote Similarity	NPD3554	Approved
0.6805	Remote Similarity	NPD3555	Approved
0.6805	Remote Similarity	NPD3552	Approved
0.6805	Remote Similarity	NPD3553	Approved
0.6788	Remote Similarity	NPD7979	Clinical (unspecified phase)
0.6784	Remote Similarity	NPD6256	Approved
0.6784	Remote Similarity	NPD6254	Approved
0.6784	Remote Similarity	NPD6255	Approved
0.678	Remote Similarity	NPD6187	Approved
0.6779	Remote Similarity	NPD8405	Clinical (unspecified phase)
0.677	Remote Similarity	NPD4761	Approved
0.677	Remote Similarity	NPD4762	Approved
0.6766	Remote Similarity	NPD5729	Clinical (unspecified phase)
0.675	Remote Similarity	NPD8163	Clinical (unspecified phase)
0.675	Remote Similarity	NPD8162	Phase 2
0.6734	Remote Similarity	NPD6253	Approved
0.6728	Remote Similarity	NPD3072	Approved
0.6728	Remote Similarity	NPD3071	Approved
0.6728	Remote Similarity	NPD3073	Approved
0.672	Remote Similarity	NPD5445	Approved
0.672	Remote Similarity	NPD6297	Approved
0.6705	Remote Similarity	NPD2874	Phase 2
0.6703	Remote Similarity	NPD7608	Discontinued
0.6687	Remote Similarity	NPD5263	Approved
0.6686	Remote Similarity	NPD7113	Clinical (unspecified phase)
0.6686	Remote Similarity	NPD3908	Approved
0.6667	Remote Similarity	NPD2541	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6853	Approved
0.6667	Remote Similarity	NPD6851	Approved
0.6667	Remote Similarity	NPD5301	Clinical (unspecified phase)
0.6647	Remote Similarity	NPD4497	Clinical (unspecified phase)
0.6647	Remote Similarity	NPD2568	Approved
0.6647	Remote Similarity	NPD6073	Approved
0.6647	Remote Similarity	NPD5314	Approved
0.6647	Remote Similarity	NPD8173	Phase 2
0.6647	Remote Similarity	NPD8172	Phase 2
0.6634	Remote Similarity	NPD5152	Clinical (unspecified phase)
0.6627	Remote Similarity	NPD3040	Approved
0.6627	Remote Similarity	NPD4177	Approved
0.6627	Remote Similarity	NPD4175	Approved
0.6604	Remote Similarity	NPD6796	Discontinued
0.6598	Remote Similarity	NPD6089	Clinical (unspecified phase)
0.6584	Remote Similarity	NPD4504	Clinical (unspecified phase)
0.6571	Remote Similarity	NPD1967	Approved
0.6571	Remote Similarity	NPD1968	Approved
0.6571	Remote Similarity	NPD6676	Phase 2
0.6566	Remote Similarity	NPD3588	Discontinued
0.6564	Remote Similarity	NPD4706	Clinical (unspecified phase)
0.6564	Remote Similarity	NPD4157	Discontinued
0.6557	Remote Similarity	NPD7080	Clinical (unspecified phase)
0.6554	Remote Similarity	NPD6631	Clinical (unspecified phase)
0.6552	Remote Similarity	NPD6480	Clinical (unspecified phase)
0.6548	Remote Similarity	NPD6919	Clinical (unspecified phase)
0.6545	Remote Similarity	NPD5311	Approved
0.6545	Remote Similarity	NPD3125	Approved
0.6545	Remote Similarity	NPD5310	Approved
0.6538	Remote Similarity	NPD7011	Discontinued
0.6533	Remote Similarity	NPD3659	Discontinued
0.6532	Remote Similarity	NPD6897	Clinical (unspecified phase)
0.6529	Remote Similarity	NPD3059	Approved
0.6529	Remote Similarity	NPD4153	Approved
0.6529	Remote Similarity	NPD3062	Approved
0.6529	Remote Similarity	NPD3061	Approved
0.6519	Remote Similarity	NPD7267	Clinical (unspecified phase)
0.6514	Remote Similarity	NPD2458	Approved
0.6514	Remote Similarity	NPD2459	Approved
0.6514	Remote Similarity	NPD2460	Phase 3
0.6514	Remote Similarity	NPD2976	Clinical (unspecified phase)
0.6506	Remote Similarity	NPD2585	Clinical (unspecified phase)
0.6506	Remote Similarity	NPD3053	Approved
0.6506	Remote Similarity	NPD3055	Approved
0.6505	Remote Similarity	NPD6767	Clinical (unspecified phase)
0.65	Remote Similarity	NPD8315	Phase 1
0.65	Remote Similarity	NPD9568	Approved
0.6497	Remote Similarity	NPD6884	Clinical (unspecified phase)
0.6494	Remote Similarity	NPD7720	Phase 2
0.6491	Remote Similarity	NPD8643	Discontinued
0.6488	Remote Similarity	NPD4676	Approved
0.648	Remote Similarity	NPD8025	Phase 2
0.6477	Remote Similarity	NPD7132	Clinical (unspecified phase)
0.6477	Remote Similarity	NPD3400	Discontinued
0.6471	Remote Similarity	NPD6407	Approved
0.6471	Remote Similarity	NPD6405	Approved
0.6465	Remote Similarity	NPD5165	Clinical (unspecified phase)
0.6461	Remote Similarity	NPD5613	Approved
0.6461	Remote Similarity	NPD5614	Approved
0.6461	Remote Similarity	NPD6088	Approved
0.646	Remote Similarity	NPD318	Approved
0.646	Remote Similarity	NPD16	Approved
0.646	Remote Similarity	NPD856	Approved
0.646	Remote Similarity	NPD317	Approved
0.6453	Remote Similarity	NPD5725	Approved
0.6443	Remote Similarity	NPD7281	Phase 3
0.6443	Remote Similarity	NPD7280	Phase 3
0.6441	Remote Similarity	NPD7602	Clinical (unspecified phase)
0.6436	Remote Similarity	NPD7810	Phase 3
0.6436	Remote Similarity	NPD7811	Phase 3
0.6435	Remote Similarity	NPD3043	Approved
0.6435	Remote Similarity	NPD3042	Approved
0.6433	Remote Similarity	NPD5323	Approved
0.6433	Remote Similarity	NPD8416	Discontinued
0.6432	Remote Similarity	NPD4564	Clinical (unspecified phase)
0.6432	Remote Similarity	NPD4565	Clinical (unspecified phase)
0.6429	Remote Similarity	NPD8103	Clinical (unspecified phase)
0.6425	Remote Similarity	NPD5192	Clinical (unspecified phase)
0.6425	Remote Similarity	NPD5556	Clinical (unspecified phase)
0.6425	Remote Similarity	NPD6419	Discontinued
0.642	Remote Similarity	NPD2209	Approved
0.642	Remote Similarity	NPD2211	Approved
0.6416	Remote Similarity	NPD6852	Discontinued
0.641	Remote Similarity	NPD6556	Clinical (unspecified phase)
0.641	Remote Similarity	NPD6237	Clinical (unspecified phase)
0.6404	Remote Similarity	NPD7554	Discontinued
0.64	Remote Similarity	NPD2087	Approved
0.64	Remote Similarity	NPD2088	Approved
0.6393	Remote Similarity	NPD7193	Clinical (unspecified phase)
0.6389	Remote Similarity	NPD4186	Clinical (unspecified phase)
0.6386	Remote Similarity	NPD4659	Approved
0.6384	Remote Similarity	NPD5481	Discontinued
0.6378	Remote Similarity	NPD6967	Phase 2
0.6374	Remote Similarity	NPD5747	Discontinued
0.6369	Remote Similarity	NPD3987	Approved
0.6369	Remote Similarity	NPD3988	Approved
0.6369	Remote Similarity	NPD7892	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD2853	Approved
0.6364	Remote Similarity	NPD6377	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD3803	Clinical (unspecified phase)
0.6358	Remote Similarity	NPD3052	Approved
0.6358	Remote Similarity	NPD3054	Approved
0.6348	Remote Similarity	NPD7910	Clinical (unspecified phase)
0.6348	Remote Similarity	NPD8323	Discontinued
0.6343	Remote Similarity	NPD8356	Approved
0.6341	Remote Similarity	NPD7342	Discontinued
0.6337	Remote Similarity	NPD6623	Phase 3
0.6337	Remote Similarity	NPD6346	Approved
0.6337	Remote Similarity	NPD7282	Approved
0.6333	Remote Similarity	NPD3985	Discontinued
0.6325	Remote Similarity	NPD2584	Suspended
0.6324	Remote Similarity	NPD4567	Approved
0.6324	Remote Similarity	NPD4514	Approved
0.6324	Remote Similarity	NPD4566	Approved
0.6321	Remote Similarity	NPD5484	Approved
0.6321	Remote Similarity	NPD5485	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