NPASS Compound

Structure

NPC165285 OpenBabel07101718292D 61 64 0 0 1 0 0 0 0 0999 V2000 -6.5555 4.9755 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.7710 5.8786 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0318 3.0375 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.7184 4.4286 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.0865 4.6031 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.1707 5.0048 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.1965 3.6092 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.3709 0.2354 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0268 -1.6178 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.3649 4.4126 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.3907 3.0169 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4165 -0.0631 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9293 -1.3246 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1779 6.7094 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3118 8.2094 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4595 5.5448 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0439 7.2094 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1779 8.7094 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4200 5.0689 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.1066 -0.4418 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6011 -0.7992 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4458 6.7094 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5816 2.4208 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.8261 4.8801 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.9476 2.6358 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.3118 7.2094 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.4749 3.4186 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4458 5.7094 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.0439 8.2094 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6808 0.6142 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.3361 1.4514 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.9458 -0.3247 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.0973 4.3331 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9889 4.3331 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.2277 1.4514 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0576 1.6419 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.6692 2.8264 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9458 -0.3247 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3117 5.0689 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4732 2.4208 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7891 0.6142 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.7968 -0.8206 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.5781 -1.7964 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -8.7512 -0.5221 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -7.0610 -0.1433 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 1.4990 3.4174 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 3.7534 3.2281 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -2.4322 5.5448 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -2.8916 0.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 2.2519 1.0497 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -4.3906 3.4174 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 -4.9099 8.7094 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.9345 4.8801 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.1435 1.0497 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.9734 1.2402 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.7792 1.8325 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.1104 -1.3111 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.9259 5.8580 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.4698 2.3382 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.5249 -0.0631 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 4 1 0 0 0 0 4 24 1 0 0 0 0 5 6 2 0 0 0 0 5 7 1 0 0 0 0 6 10 1 0 0 0 0 7 11 2 0 0 0 0 8 12 1 0 0 0 0 8 20 1 0 0 0 0 9 13 1 0 0 0 0 9 21 1 0 0 0 0 10 27 2 0 0 0 0 11 27 1 0 0 0 0 14 17 1 0 0 0 0 14 26 2 0 0 0 0 15 18 2 0 0 0 0 15 26 1 0 0 0 0 16 19 2 0 0 0 0 16 28 1 0 0 0 0 17 29 2 0 0 0 0 18 29 1 0 0 0 0 19 33 1 0 0 0 0 20 45 1 0 0 0 0 21 52 1 0 0 0 0 22 26 1 0 0 0 0 23 31 1 0 0 0 0 23 46 1 0 0 0 0 24 2 1 6 0 0 0 25 3 1 6 0 0 0 25 36 1 0 0 0 0 25 47 1 0 0 0 0 27 37 1 0 0 0 0 28 22 1 1 0 0 0 28 48 1 0 0 0 0 29 53 1 0 0 0 0 30 12 1 1 0 0 0 30 35 1 0 0 0 0 30 49 1 0 0 0 0 31 41 1 0 0 0 0 31 50 1 6 0 0 0 32 13 1 1 0 0 0 32 38 1 0 0 0 0 32 52 1 0 0 0 0 33 46 2 3 0 0 0 33 54 1 0 0 0 0 34 24 1 6 0 0 0 34 39 1 0 0 0 0 34 51 1 0 0 0 0 35 40 1 0 0 0 0 35 55 2 0 0 0 0 36 50 2 3 0 0 0 36 56 1 0 0 0 0 37 47 2 3 0 0 0 37 57 1 0 0 0 0 38 49 2 3 0 0 0 38 58 1 0 0 0 0 39 48 2 3 0 0 0 39 59 1 0 0 0 0 40 51 1 0 0 0 0 40 60 2 0 0 0 0 41 52 1 0 0 0 0 41 61 2 0 0 0 0 42 43 2 0 0 0 0 42 44 1 0 0 0 0 42 45 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	844.42
Volume:	847.658
LogP:	-0.015
LogD:	0.385
LogS:	-3.892
# Rotatable Bonds:	15
TPSA:	297.6
# H-Bond Aceptor:	19
# H-Bond Donor:	11
# Rings:	4
# Heavy Atoms:	19

MedChem Properties

QED Drug-Likeness Score:	0.059
Synthetic Accessibility Score:	5.758
Fsp3:	0.452
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:	-6.718
MDCK Permeability:	8.025337592698634e-06
Pgp-inhibitor:	0.024
Pgp-substrate:	1.0
Human Intestinal Absorption (HIA):	0.971
20% Bioavailability (F20%):	0.997
30% Bioavailability (F30%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.053
Plasma Protein Binding (PPB):	33.8671989440918%
Volume Distribution (VD):	0.32
Pgp-substrate:	57.293174743652344%

ADMET: Metabolism

CYP1A2-inhibitor:	0.001
CYP1A2-substrate:	0.004
CYP2C19-inhibitor:	0.049
CYP2C19-substrate:	0.033
CYP2C9-inhibitor:	0.15
CYP2C9-substrate:	0.033
CYP2D6-inhibitor:	0.012
CYP2D6-substrate:	0.124
CYP3A4-inhibitor:	0.045
CYP3A4-substrate:	0.01

ADMET: Excretion

Clearance (CL):	2.5
Half-life (T1/2):	0.602

ADMET: Toxicity

hERG Blockers:	0.136
Human Hepatotoxicity (H-HT):	0.84
Drug-inuced Liver Injury (DILI):	0.798
AMES Toxicity:	0.008
Rat Oral Acute Toxicity:	0.198
Maximum Recommended Daily Dose:	0.964
Skin Sensitization:	0.175
Carcinogencity:	0.191
Eye Corrosion:	0.003
Eye Irritation:	0.004
Respiratory Toxicity:	0.929

Download Data

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

Natural Product: NPC165285

Natural Product ID:	NPC165285
*Common Name:**	Cyclotheonamide E2
IUPAC Name:	N-[(2S)-1-[[(3S,7E,9S,12R,16S,19S)-12-[(2S)-butan-2-yl]-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]amino]-1-oxopropan-2-yl]benzamide
Synonyms:	Cyclotheonamide E2
Standard InCHIKey:	YSNKBNIOHORIHX-MSQPAANESA-N
Standard InCHI:	InChI=1S/C42H56N10O9/c1-4-24(2)34-39(59)48-28(22-26-14-17-29(53)18-15-26)16-19-33(54)46-23-31(50-36(56)25(3)47-37(57)27-10-6-5-7-11-27)41(61)52-21-9-13-32(52)38(58)49-30(35(55)40(60)51-34)12-8-20-45-42(43)44/h5-7,10-11,14-19,24-25,28,30-32,34,53H,4,8-9,12-13,20-23H2,1-3H3,(H,46,54)(H,47,57)(H,48,59)(H,49,58)(H,50,56)(H,51,60)(H4,43,44,45)/b19-16+/t24-,25-,28+,30-,31-,32-,34+/m0/s1
SMILES:	CC[C@@H]([C@H]1NC(=O)C(=O)[C@H](CCCNC(=N)N)N=C(O)[C@@H]2CCCN2C(=O)[C@H](CN=C(/C=C/[C@@H](N=C1O)Cc1ccc(cc1)O)O)N=C([C@@H](N=C(c1ccccc1)O)C)O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL505589
PubChem CID:	11491382
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:0004831] Oligopeptides

*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	2

Activity Type	# Activity
Individual Protein	1
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT670	Individual Protein	Thrombin	Homo sapiens	IC50	=	13.0	nM	PMID[465153]
NPT2	Others	Unspecified		IC50	=	55.0	nM	PMID[465153]

☑ 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 NPC165285 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	258
0.1-0.2	1600
0.2-0.3	10817
0.3-0.4	7202
0.4-0.5	17887
0.5-0.6	3964
0.6-0.7	700
0.7-0.8	209
0.8-0.85	42
0.85-0.9	13
0.9-0.95	0
0.95-1	5

Similarity Score	Similarity Level	Natural Product ID
0.9936	High Similarity	NPC475532
0.9744	High Similarity	NPC129486
0.9623	High Similarity	NPC17698
0.9074	High Similarity	NPC274198
0.9074	High Similarity	NPC198254
0.8957	High Similarity	NPC276506
0.8855	High Similarity	NPC196243
0.878	High Similarity	NPC280022
0.8642	High Similarity	NPC469243
0.8588	High Similarity	NPC153554
0.8535	High Similarity	NPC16188
0.8529	High Similarity	NPC97526
0.8529	High Similarity	NPC119652
0.8528	High Similarity	NPC475544
0.85	High Similarity	NPC202198
0.8485	Intermediate Similarity	NPC223207
0.8438	Intermediate Similarity	NPC233702
0.8434	Intermediate Similarity	NPC471771
0.8434	Intermediate Similarity	NPC304074
0.8434	Intermediate Similarity	NPC290755
0.8409	Intermediate Similarity	NPC61332
0.8409	Intermediate Similarity	NPC240130
0.8395	Intermediate Similarity	NPC473580
0.8383	Intermediate Similarity	NPC328649
0.8364	Intermediate Similarity	NPC241794
0.8333	Intermediate Similarity	NPC476989
0.8324	Intermediate Similarity	NPC473404
0.8323	Intermediate Similarity	NPC61004
0.8302	Intermediate Similarity	NPC311658
0.8295	Intermediate Similarity	NPC94862
0.8272	Intermediate Similarity	NPC5194
0.8272	Intermediate Similarity	NPC261934
0.8272	Intermediate Similarity	NPC56685
0.8266	Intermediate Similarity	NPC475409
0.8266	Intermediate Similarity	NPC170302
0.8266	Intermediate Similarity	NPC475564
0.8263	Intermediate Similarity	NPC63931
0.8167	Intermediate Similarity	NPC302715
0.8166	Intermediate Similarity	NPC141957
0.816	Intermediate Similarity	NPC262166
0.815	Intermediate Similarity	NPC473546
0.8148	Intermediate Similarity	NPC473491
0.8133	Intermediate Similarity	NPC244336
0.8122	Intermediate Similarity	NPC477638
0.8122	Intermediate Similarity	NPC477632
0.8072	Intermediate Similarity	NPC326349
0.8072	Intermediate Similarity	NPC323336
0.8059	Intermediate Similarity	NPC302597
0.8045	Intermediate Similarity	NPC102959
0.8013	Intermediate Similarity	NPC267237
0.8	Intermediate Similarity	NPC60516
0.7977	Intermediate Similarity	NPC137627
0.7965	Intermediate Similarity	NPC475123
0.7965	Intermediate Similarity	NPC475204
0.7952	Intermediate Similarity	NPC244509
0.7931	Intermediate Similarity	NPC26108
0.7925	Intermediate Similarity	NPC48202
0.7907	Intermediate Similarity	NPC66490
0.7901	Intermediate Similarity	NPC477636
0.7889	Intermediate Similarity	NPC96275
0.788	Intermediate Similarity	NPC329295
0.7874	Intermediate Similarity	NPC306804
0.7862	Intermediate Similarity	NPC242159
0.7862	Intermediate Similarity	NPC313694
0.7861	Intermediate Similarity	NPC46009
0.7844	Intermediate Similarity	NPC476268
0.7829	Intermediate Similarity	NPC471165
0.7814	Intermediate Similarity	NPC477631
0.7812	Intermediate Similarity	NPC214988
0.7802	Intermediate Similarity	NPC51047
0.7797	Intermediate Similarity	NPC194671
0.7797	Intermediate Similarity	NPC269750
0.7784	Intermediate Similarity	NPC477639
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	NPC107938
0.7644	Intermediate Similarity	NPC294516
0.7627	Intermediate Similarity	NPC476227
0.7619	Intermediate Similarity	NPC469443
0.7619	Intermediate Similarity	NPC477551
0.7614	Intermediate Similarity	NPC230611
0.7607	Intermediate Similarity	NPC168861
0.7602	Intermediate Similarity	NPC287757
0.7602	Intermediate Similarity	NPC319320
0.7598	Intermediate Similarity	NPC45037
0.7572	Intermediate Similarity	NPC133470
0.7572	Intermediate Similarity	NPC191863
0.7572	Intermediate Similarity	NPC289776
0.7568	Intermediate Similarity	NPC470728
0.7547	Intermediate Similarity	NPC326966
0.7544	Intermediate Similarity	NPC324850
0.754	Intermediate Similarity	NPC80514
0.7531	Intermediate Similarity	NPC132636
0.7528	Intermediate Similarity	NPC473402
0.7528	Intermediate Similarity	NPC159767
0.7528	Intermediate Similarity	NPC155506
0.7526	Intermediate Similarity	NPC478005
0.7514	Intermediate Similarity	NPC328494
0.75	Intermediate Similarity	NPC324081
0.7472	Intermediate Similarity	NPC248670
0.7457	Intermediate Similarity	NPC114806
0.7438	Intermediate Similarity	NPC257390
0.7432	Intermediate Similarity	NPC294951
0.743	Intermediate Similarity	NPC473354
0.7418	Intermediate Similarity	NPC477637
0.7399	Intermediate Similarity	NPC24617
0.7391	Intermediate Similarity	NPC299806
0.7386	Intermediate Similarity	NPC254700
0.7385	Intermediate Similarity	NPC220060
0.7375	Intermediate Similarity	NPC255447
0.7353	Intermediate Similarity	NPC300443
0.7347	Intermediate Similarity	NPC469444
0.7333	Intermediate Similarity	NPC158277
0.733	Intermediate Similarity	NPC472923
0.7312	Intermediate Similarity	NPC325651
0.7299	Intermediate Similarity	NPC1390
0.7299	Intermediate Similarity	NPC62104
0.7291	Intermediate Similarity	NPC478007
0.7262	Intermediate Similarity	NPC81026
0.7254	Intermediate Similarity	NPC473450
0.725	Intermediate Similarity	NPC473322
0.7247	Intermediate Similarity	NPC209463
0.7246	Intermediate Similarity	NPC323244
0.7246	Intermediate Similarity	NPC326241
0.7244	Intermediate Similarity	NPC71684
0.7243	Intermediate Similarity	NPC471049
0.7243	Intermediate Similarity	NPC471048
0.7243	Intermediate Similarity	NPC471050
0.7236	Intermediate Similarity	NPC469445
0.7234	Intermediate Similarity	NPC163961
0.7234	Intermediate Similarity	NPC473305
0.7228	Intermediate Similarity	NPC476321
0.7225	Intermediate Similarity	NPC469903
0.722	Intermediate Similarity	NPC478008
0.7208	Intermediate Similarity	NPC219350
0.7208	Intermediate Similarity	NPC194699
0.7204	Intermediate Similarity	NPC235194
0.7204	Intermediate Similarity	NPC138083
0.7202	Intermediate Similarity	NPC266741
0.719	Intermediate Similarity	NPC328924
0.7189	Intermediate Similarity	NPC471526
0.7174	Intermediate Similarity	NPC32064
0.7168	Intermediate Similarity	NPC473002
0.7168	Intermediate Similarity	NPC39431
0.7159	Intermediate Similarity	NPC473003
0.7159	Intermediate Similarity	NPC469902
0.7152	Intermediate Similarity	NPC109580
0.7143	Intermediate Similarity	NPC164608
0.7135	Intermediate Similarity	NPC5719
0.7135	Intermediate Similarity	NPC217804
0.7135	Intermediate Similarity	NPC210377
0.7135	Intermediate Similarity	NPC22883
0.712	Intermediate Similarity	NPC475421
0.7118	Intermediate Similarity	NPC119569
0.7115	Intermediate Similarity	NPC283760
0.7111	Intermediate Similarity	NPC186617
0.711	Intermediate Similarity	NPC122590
0.7107	Intermediate Similarity	NPC81845
0.7095	Intermediate Similarity	NPC15068
0.7093	Intermediate Similarity	NPC475168
0.7093	Intermediate Similarity	NPC7817
0.7073	Intermediate Similarity	NPC244866
0.7072	Intermediate Similarity	NPC473693
0.7072	Intermediate Similarity	NPC471568
0.707	Intermediate Similarity	NPC200964
0.7065	Intermediate Similarity	NPC277306
0.7065	Intermediate Similarity	NPC469442
0.7059	Intermediate Similarity	NPC473804
0.7056	Intermediate Similarity	NPC63040
0.7055	Intermediate Similarity	NPC130309
0.7051	Intermediate Similarity	NPC470546
0.7037	Intermediate Similarity	NPC329731
0.7037	Intermediate Similarity	NPC111428
0.7031	Intermediate Similarity	NPC328763
0.7021	Intermediate Similarity	NPC315542
0.7017	Intermediate Similarity	NPC315388
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	NPC209509
0.7	Intermediate Similarity	NPC316008
0.7	Intermediate Similarity	NPC234069
0.7	Intermediate Similarity	NPC313867
0.6995	Remote Similarity	NPC59827
0.6995	Remote Similarity	NPC184933
0.6995	Remote Similarity	NPC25539
0.6994	Remote Similarity	NPC200589
0.6988	Remote Similarity	NPC314835
0.6987	Remote Similarity	NPC470545
0.6984	Remote Similarity	NPC276120
0.6977	Remote Similarity	NPC9373

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 NPC165285 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	158
0.1-0.2	426
0.2-0.3	752
0.3-0.4	1330
0.4-0.5	3686
0.5-0.6	2471
0.6-0.7	291
0.7-0.8	32
0.8-0.85	3
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9006	High Similarity	NPD8303	Discontinued
0.8202	Intermediate Similarity	NPD7617	Discontinued
0.816	Intermediate Similarity	NPD7523	Phase 3
0.814	Intermediate Similarity	NPD5200	Clinical (unspecified phase)
0.8133	Intermediate Similarity	NPD7495	Discontinued
0.8133	Intermediate Similarity	NPD8019	Approved
0.8072	Intermediate Similarity	NPD7118	Clinical (unspecified phase)
0.7914	Intermediate Similarity	NPD8290	Clinical (unspecified phase)
0.7784	Intermediate Similarity	NPD6670	Clinical (unspecified phase)
0.7716	Intermediate Similarity	NPD8076	Discontinued
0.7683	Intermediate Similarity	NPD7066	Clinical (unspecified phase)
0.7665	Intermediate Similarity	NPD6078	Clinical (unspecified phase)
0.7607	Intermediate Similarity	NPD6809	Clinical (unspecified phase)
0.7578	Intermediate Similarity	NPD4782	Clinical (unspecified phase)
0.7562	Intermediate Similarity	NPD4791	Clinical (unspecified phase)
0.756	Intermediate Similarity	NPD7303	Discontinued
0.7546	Intermediate Similarity	NPD7450	Phase 2
0.7485	Intermediate Similarity	NPD7728	Clinical (unspecified phase)
0.7458	Intermediate Similarity	NPD4652	Approved
0.7429	Intermediate Similarity	NPD2098	Approved
0.7423	Intermediate Similarity	NPD6901	Phase 3
0.7405	Intermediate Similarity	NPD5339	Clinical (unspecified phase)
0.7349	Intermediate Similarity	NPD5341	Clinical (unspecified phase)
0.7329	Intermediate Similarity	NPD1329	Clinical (unspecified phase)
0.7329	Intermediate Similarity	NPD1330	Phase 2
0.7314	Intermediate Similarity	NPD2097	Approved
0.731	Intermediate Similarity	NPD7131	Phase 3
0.7303	Intermediate Similarity	NPD7485	Phase 3
0.7303	Intermediate Similarity	NPD7484	Phase 3
0.7222	Intermediate Similarity	NPD3632	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD5137	Approved
0.7195	Intermediate Similarity	NPD4757	Clinical (unspecified phase)
0.7193	Intermediate Similarity	NPD5348	Clinical (unspecified phase)
0.7163	Intermediate Similarity	NPD8292	Phase 2
0.7112	Intermediate Similarity	NPD5946	Clinical (unspecified phase)
0.7104	Intermediate Similarity	NPD8022	Clinical (unspecified phase)
0.7066	Intermediate Similarity	NPD6866	Clinical (unspecified phase)
0.7066	Intermediate Similarity	NPD6867	Clinical (unspecified phase)
0.7055	Intermediate Similarity	NPD3136	Phase 2
0.7052	Intermediate Similarity	NPD7613	Discontinued
0.7041	Intermediate Similarity	NPD6681	Discovery
0.7027	Intermediate Similarity	NPD7695	Clinical (unspecified phase)
0.7017	Intermediate Similarity	NPD2890	Approved
0.7017	Intermediate Similarity	NPD2889	Approved
0.7017	Intermediate Similarity	NPD2888	Approved
0.7017	Intermediate Similarity	NPD2017	Approved
0.7	Intermediate Similarity	NPD6860	Clinical (unspecified phase)
0.6994	Remote Similarity	NPD7979	Clinical (unspecified phase)
0.6982	Remote Similarity	NPD7978	Discontinued
0.6975	Remote Similarity	NPD7451	Discontinued
0.6942	Remote Similarity	NPD8405	Clinical (unspecified phase)
0.6936	Remote Similarity	NPD6682	Clinical (unspecified phase)
0.6912	Remote Similarity	NPD6189	Approved
0.6912	Remote Similarity	NPD6188	Approved
0.689	Remote Similarity	NPD5263	Approved
0.6869	Remote Similarity	NPD6255	Approved
0.6869	Remote Similarity	NPD6256	Approved
0.6869	Remote Similarity	NPD6254	Approved
0.6867	Remote Similarity	NPD5729	Clinical (unspecified phase)
0.6864	Remote Similarity	NPD5301	Clinical (unspecified phase)
0.6863	Remote Similarity	NPD6187	Approved
0.6848	Remote Similarity	NPD4497	Clinical (unspecified phase)
0.6833	Remote Similarity	NPD5967	Approved
0.6832	Remote Similarity	NPD3072	Approved
0.6832	Remote Similarity	NPD3073	Approved
0.6832	Remote Similarity	NPD3071	Approved
0.6818	Remote Similarity	NPD6253	Approved
0.6809	Remote Similarity	NPD5445	Approved
0.6805	Remote Similarity	NPD3552	Approved
0.6805	Remote Similarity	NPD3554	Approved
0.6805	Remote Similarity	NPD3555	Approved
0.6805	Remote Similarity	NPD3553	Approved
0.6793	Remote Similarity	NPD7608	Discontinued
0.6771	Remote Similarity	NPD6089	Clinical (unspecified phase)
0.677	Remote Similarity	NPD4762	Approved
0.677	Remote Similarity	NPD4761	Approved
0.6758	Remote Similarity	NPD8031	Discontinued
0.6754	Remote Similarity	NPD6557	Phase 2
0.6748	Remote Similarity	NPD3125	Approved
0.6747	Remote Similarity	NPD6919	Clinical (unspecified phase)
0.6746	Remote Similarity	NPD8172	Phase 2
0.6746	Remote Similarity	NPD8173	Phase 2
0.6746	Remote Similarity	NPD6073	Approved
0.6743	Remote Similarity	NPD6631	Clinical (unspecified phase)
0.6728	Remote Similarity	NPD2562	Approved
0.6728	Remote Similarity	NPD2561	Approved
0.6727	Remote Similarity	NPD3040	Approved
0.6725	Remote Similarity	NPD6897	Clinical (unspecified phase)
0.672	Remote Similarity	NPD6297	Approved
0.6716	Remote Similarity	NPD6480	Clinical (unspecified phase)
0.6687	Remote Similarity	NPD4676	Approved
0.6686	Remote Similarity	NPD8643	Discontinued
0.6686	Remote Similarity	NPD3908	Approved
0.6686	Remote Similarity	NPD7113	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6853	Approved
0.6667	Remote Similarity	NPD6851	Approved
0.6648	Remote Similarity	NPD6088	Approved
0.6627	Remote Similarity	NPD4177	Approved
0.6627	Remote Similarity	NPD4175	Approved
0.6611	Remote Similarity	NPD7267	Clinical (unspecified phase)
0.661	Remote Similarity	NPD5556	Clinical (unspecified phase)
0.661	Remote Similarity	NPD2874	Phase 2
0.6606	Remote Similarity	NPD3055	Approved
0.6606	Remote Similarity	NPD2585	Clinical (unspecified phase)
0.6606	Remote Similarity	NPD3053	Approved
0.6591	Remote Similarity	NPD6884	Clinical (unspecified phase)
0.659	Remote Similarity	NPD7720	Phase 2
0.6584	Remote Similarity	NPD4504	Clinical (unspecified phase)
0.6584	Remote Similarity	NPD8163	Clinical (unspecified phase)
0.6584	Remote Similarity	NPD8162	Phase 2
0.658	Remote Similarity	NPD6556	Clinical (unspecified phase)
0.6573	Remote Similarity	NPD4186	Clinical (unspecified phase)
0.6571	Remote Similarity	NPD6676	Phase 2
0.6571	Remote Similarity	NPD1967	Approved
0.6571	Remote Similarity	NPD1968	Approved
0.6564	Remote Similarity	NPD8025	Phase 2
0.6564	Remote Similarity	NPD4706	Clinical (unspecified phase)
0.6562	Remote Similarity	NPD7132	Clinical (unspecified phase)
0.6557	Remote Similarity	NPD7080	Clinical (unspecified phase)
0.6554	Remote Similarity	NPD5613	Approved
0.6554	Remote Similarity	NPD5614	Approved
0.6552	Remote Similarity	NPD5152	Clinical (unspecified phase)
0.655	Remote Similarity	NPD2568	Approved
0.655	Remote Similarity	NPD5725	Approved
0.6545	Remote Similarity	NPD5311	Approved
0.6545	Remote Similarity	NPD5310	Approved
0.6534	Remote Similarity	NPD7602	Clinical (unspecified phase)
0.6529	Remote Similarity	NPD4153	Approved
0.6529	Remote Similarity	NPD6346	Approved
0.6529	Remote Similarity	NPD5323	Approved
0.6528	Remote Similarity	NPD7280	Phase 3
0.6528	Remote Similarity	NPD7281	Phase 3
0.6526	Remote Similarity	NPD6796	Discontinued
0.6522	Remote Similarity	NPD4565	Clinical (unspecified phase)
0.6522	Remote Similarity	NPD4564	Clinical (unspecified phase)
0.6514	Remote Similarity	NPD2209	Approved
0.6514	Remote Similarity	NPD2459	Approved
0.6514	Remote Similarity	NPD2211	Approved
0.6514	Remote Similarity	NPD2458	Approved
0.6514	Remote Similarity	NPD2460	Phase 3
0.651	Remote Similarity	NPD5192	Clinical (unspecified phase)
0.6505	Remote Similarity	NPD6767	Clinical (unspecified phase)
0.65	Remote Similarity	NPD7282	Approved
0.65	Remote Similarity	NPD8315	Phase 1
0.65	Remote Similarity	NPD9568	Approved
0.6494	Remote Similarity	NPD2087	Approved
0.6494	Remote Similarity	NPD2088	Approved
0.6492	Remote Similarity	NPD5484	Approved
0.6492	Remote Similarity	NPD5485	Approved
0.6485	Remote Similarity	NPD4677	Discontinued
0.6484	Remote Similarity	NPD7193	Clinical (unspecified phase)
0.6484	Remote Similarity	NPD2541	Clinical (unspecified phase)
0.648	Remote Similarity	NPD4157	Discontinued
0.6477	Remote Similarity	NPD5481	Discontinued
0.6471	Remote Similarity	NPD7086	Phase 2
0.6461	Remote Similarity	NPD3988	Approved
0.6461	Remote Similarity	NPD7892	Clinical (unspecified phase)
0.6461	Remote Similarity	NPD3987	Approved
0.6453	Remote Similarity	NPD5314	Approved
0.645	Remote Similarity	NPD3659	Discontinued
0.6448	Remote Similarity	NPD7011	Discontinued
0.6448	Remote Similarity	NPD3589	Clinical (unspecified phase)
0.6447	Remote Similarity	NPD6836	Approved
0.6447	Remote Similarity	NPD6377	Clinical (unspecified phase)
0.6436	Remote Similarity	NPD7811	Phase 3
0.6436	Remote Similarity	NPD7810	Phase 3
0.6433	Remote Similarity	NPD8416	Discontinued
0.6429	Remote Similarity	NPD8103	Clinical (unspecified phase)
0.642	Remote Similarity	NPD5304	Approved
0.642	Remote Similarity	NPD5303	Approved
0.6416	Remote Similarity	NPD4214	Discontinued
0.6416	Remote Similarity	NPD6852	Discontinued
0.6413	Remote Similarity	NPD4566	Approved
0.6413	Remote Similarity	NPD4567	Approved
0.6412	Remote Similarity	NPD5581	Approved
0.6412	Remote Similarity	NPD5299	Approved
0.6406	Remote Similarity	NPD5557	Phase 1
0.6404	Remote Similarity	NPD7554	Discontinued
0.6402	Remote Similarity	NPD3421	Phase 3
0.6396	Remote Similarity	NPD6835	Approved
0.6393	Remote Similarity	NPD2468	Approved
0.6393	Remote Similarity	NPD2469	Approved
0.6391	Remote Similarity	NPD4125	Approved
0.6387	Remote Similarity	NPD3909	Discontinued
0.6386	Remote Similarity	NPD4659	Approved
0.6386	Remote Similarity	NPD5856	Discontinued
0.6383	Remote Similarity	NPD3286	Discontinued
0.6382	Remote Similarity	NPD5165	Clinical (unspecified phase)
0.6378	Remote Similarity	NPD6967	Phase 2
0.6377	Remote Similarity	NPD8493	Clinical (unspecified phase)
0.6374	Remote Similarity	NPD7634	Clinical (unspecified phase)
0.6374	Remote Similarity	NPD6523	Clinical (unspecified phase)
0.6374	Remote Similarity	NPD5747	Discontinued
0.6369	Remote Similarity	NPD3588	Discontinued
0.6358	Remote Similarity	NPD317	Approved
0.6358	Remote Similarity	NPD856	Approved
0.6358	Remote Similarity	NPD16	Approved
0.6358	Remote Similarity	NPD318	Approved
0.6355	Remote Similarity	NPD3814	Phase 1
0.6354	Remote Similarity	NPD8362	Clinical (unspecified phase)

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