NPASS Compound

Structure

NPC219350 OpenBabel07101719132D 63 65 0 0 1 0 0 0 0 0999 V2000 0.1229 -7.9814 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2903 0.0722 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0489 -1.4268 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8537 -7.1055 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8266 1.2280 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3146 -5.6180 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.3341 -1.2280 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3464 -3.7743 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1763 -7.0130 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0848 -0.3347 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9252 -1.2914 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.6541 -4.1378 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0028 -3.8353 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.4941 -3.6529 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1618 -3.9689 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.9932 0.0054 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8142 -2.6829 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1342 -4.6228 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4638 3.3394 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2369 -0.8963 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0417 -6.5750 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.9333 0.2639 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.8142 -3.6529 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.6541 -2.1980 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0168 -1.6315 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.6316 -4.4096 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.2942 -4.1378 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 4.1774 2.6825 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.4941 -2.6829 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7419 -4.7097 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.3715 -1.3342 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.9018 0.2105 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.0952 -5.6066 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 4.2028 -2.5834 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6343 -3.2295 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9653 1.7360 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8004 -0.1545 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9364 -5.0859 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1487 -5.3945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7971 -0.5527 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.0612 1.3022 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.6541 -1.2280 0.0000 Cl 0 0 0 0 0 0 0 0 0 0 0 0 7.8099 0.6856 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 7.2208 2.2589 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 6.1528 0.9621 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 3.5319 -0.7915 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 4.0695 -3.5442 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -1.6610 -2.2599 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 2.1139 1.1569 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -0.6776 -4.8865 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 2.0592 -5.4999 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 3.6759 4.2858 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.1031 2.9720 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.1723 -2.5567 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5862 -3.4154 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.6789 1.0791 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.3084 0.6718 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4890 -5.8830 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.2163 -6.2931 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.4734 0.1426 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.3341 -2.1980 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.7741 -4.6448 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 1 9 1 0 0 0 0 2 20 1 0 0 0 0 3 20 1 0 0 0 0 6 50 1 0 0 0 0 7 61 1 0 0 0 0 8 62 1 0 0 0 0 9 21 1 0 0 0 0 10 11 1 0 0 0 0 10 16 1 0 0 0 0 12 14 2 0 0 0 0 12 23 1 0 0 0 0 13 15 1 0 0 0 0 14 29 1 0 0 0 0 15 30 1 0 0 0 0 16 45 1 0 0 0 0 17 23 2 0 0 0 0 17 24 1 0 0 0 0 18 23 1 0 0 0 0 19 28 1 0 0 0 0 19 52 1 0 0 0 0 21 4 1 1 0 0 0 22 5 1 6 0 0 0 22 32 1 0 0 0 0 22 63 1 0 0 0 0 24 29 2 0 0 0 0 24 42 1 0 0 0 0 25 11 1 1 0 0 0 25 34 1 0 0 0 0 25 46 1 0 0 0 0 26 13 1 1 0 0 0 26 38 1 0 0 0 0 26 47 1 0 0 0 0 27 18 1 1 0 0 0 27 35 1 0 0 0 0 27 50 1 0 0 0 0 28 36 1 0 0 0 0 28 53 1 1 0 0 0 29 61 1 0 0 0 0 30 51 1 0 0 0 0 30 62 1 6 0 0 0 31 20 1 1 0 0 0 31 40 1 0 0 0 0 31 48 1 0 0 0 0 32 37 1 0 0 0 0 32 49 1 6 0 0 0 33 21 1 1 0 0 0 33 39 1 0 0 0 0 33 51 1 0 0 0 0 34 47 2 3 0 0 0 34 54 1 0 0 0 0 35 48 2 3 0 0 0 35 55 1 0 0 0 0 36 49 2 3 0 0 0 36 56 1 0 0 0 0 37 46 2 3 0 0 0 37 57 1 0 0 0 0 38 51 1 0 0 0 0 38 58 2 0 0 0 0 39 50 1 0 0 0 0 39 59 2 0 0 0 0 40 60 2 0 0 0 0 40 63 1 0 0 0 0 41 43 2 0 0 0 0 41 44 1 0 0 0 0 41 45 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	909.44
Volume:	882.686
LogP:	0.617
LogD:	0.31
LogS:	-2.126
# Rotatable Bonds:	16
TPSA:	304.14
# H-Bond Aceptor:	21
# H-Bond Donor:	10
# Rings:	3
# Heavy Atoms:	22

MedChem Properties

QED Drug-Likeness Score:	0.046
Synthetic Accessibility Score:	6.781
Fsp3:	0.659
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:	-6.792
MDCK Permeability:	3.352672138134949e-05
Pgp-inhibitor:	0.712
Pgp-substrate:	1.0
Human Intestinal Absorption (HIA):	0.882
20% Bioavailability (F20%):	0.955
30% Bioavailability (F30%):	0.981

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.071
Plasma Protein Binding (PPB):	63.64691162109375%
Volume Distribution (VD):	0.387
Pgp-substrate:	23.596750259399414%

ADMET: Metabolism

CYP1A2-inhibitor:	0.0
CYP1A2-substrate:	0.014
CYP2C19-inhibitor:	0.036
CYP2C19-substrate:	0.046
CYP2C9-inhibitor:	0.079
CYP2C9-substrate:	0.017
CYP2D6-inhibitor:	0.003
CYP2D6-substrate:	0.084
CYP3A4-inhibitor:	0.094
CYP3A4-substrate:	0.039

ADMET: Excretion

Clearance (CL):	3.457
Half-life (T1/2):	0.46

ADMET: Toxicity

hERG Blockers:	0.031
Human Hepatotoxicity (H-HT):	0.937
Drug-inuced Liver Injury (DILI):	0.955
AMES Toxicity:	0.007
Rat Oral Acute Toxicity:	0.389
Maximum Recommended Daily Dose:	0.92
Skin Sensitization:	0.089
Carcinogencity:	0.028
Eye Corrosion:	0.003
Eye Irritation:	0.003
Respiratory Toxicity:	0.045

Download Data

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

Natural Product: NPC219350

Natural Product ID:	NPC219350
*Common Name:**	Amino(3-((2S,5S,8S,11R,12S,15S,18S,21R)-2-Sec-Butyl-5-(3-Chloro-4-Methoxybenzyl)-12-((R)-2,3-Dihydroxypropanamido)-8-Isopropyl-21-Methoxy-4,11-Dimethyl-3,6,9,13,16,22-Hexaoxo-10-Oxa-1,4,7,14,17-Pentaazabicyclo[16.3.1]Docosan-15-Yl)Propylamino)Methaniminium
IUPAC Name:	(2R)-N-[(2S,5S,8S,11R,12S,15S,18S,21R)-2-[(2S)-butan-2-yl]-5-[(3-chloro-4-methoxyphenyl)methyl]-15-[3-(diaminomethylideneamino)propyl]-21-methoxy-4,11-dimethyl-3,6,9,13,16,22-hexaoxo-8-propan-2-yl-10-oxa-1,4,7,14,17-pentazabicyclo[16.3.1]docosan-12-yl]-2,3-dihydroxypropanamide
Synonyms:
Standard InCHIKey:	LURNUBHCAYLVKT-PDLQKTGISA-N
Standard InCHI:	InChI=1S/C41H64ClN9O12/c1-9-21(4)33-39(59)50(6)27(18-23-12-14-29(61-7)24(42)17-23)35(55)48-31(20(2)3)40(60)63-22(5)32(49-36(56)28(53)19-52)37(57)46-25(11-10-16-45-41(43)44)34(54)47-26-13-15-30(62-8)51(33)38(26)58/h12,14,17,20-22,25-28,30-33,52-53H,9-11,13,15-16,18-19H2,1-8H3,(H,46,57)(H,47,54)(H,48,55)(H,49,56)(H4,43,44,45)/t21-,22+,25-,26-,27-,28+,30+,31-,32-,33-/m0/s1
SMILES:	CC[C@@H]([C@@H]1N2[C@H](OC)CC[C@@H](C2=O)N=C(O)[C@H](CCCNC(=N)N)N=C(O)[C@H]([C@H](OC(=O)[C@@H](N=C([C@@H](N(C1=O)C)Cc1ccc(c(c1)Cl)OC)O)C(C)C)C)N=C([C@@H](CO)O)O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1078915
PubChem CID:	44254880
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
NPO3288	Microcystis aeruginosa	Species	Microcystaceae	Bacteria	n.a.	n.a.	n.a.	PMID[11000050]
NPO3288	Microcystis aeruginosa	Species	Microcystaceae	Bacteria	n.a.	n.a.	n.a.	PMID[11374973]
NPO3288	Microcystis aeruginosa	Species	Microcystaceae	Bacteria	n.a.	Einan Reservoir in Israel	n.a.	PMID[12141855]
NPO3288	Microcystis aeruginosa	Species	Microcystaceae	Bacteria	n.a.	n.a.	n.a.	PMID[12141855]
NPO3288	Microcystis aeruginosa	Species	Microcystaceae	Bacteria	n.a.	n.a.	n.a.	PMID[18163584]
NPO3288	Microcystis aeruginosa	Species	Microcystaceae	Bacteria	n.a.	n.a.	n.a.	PMID[18558743]
NPO3288	Microcystis aeruginosa	Species	Microcystaceae	Bacteria	n.a.	n.a.	n.a.	PMID[18973386]
NPO3288	Microcystis aeruginosa	Species	Microcystaceae	Bacteria	water bloom of the cyanobacterium Microcystis aeruginosa	n.a.	n.a.	PMID[19650639]
NPO3288	Microcystis aeruginosa	Species	Microcystaceae	Bacteria	bloom material	Lake Kinneret, Israel	n.a.	PMID[22280481]
NPO3288	Microcystis aeruginosa	Species	Microcystaceae	Bacteria	n.a.	Kibbutz Geva, Israel	n.a.	PMID[23153007]
NPO3288	Microcystis aeruginosa	Species	Microcystaceae	Bacteria	n.a.	Water Reservoir near Kibbutz Hafetz Haim, Israel	n.a.	PMID[23718637]
NPO3288	Microcystis aeruginosa	Species	Microcystaceae	Bacteria	Bloom	n.a.	n.a.	PMID[24261937]
NPO3288	Microcystis aeruginosa	Species	Microcystaceae	Bacteria	n.a.	n.a.	n.a.	PMID[24642434]
NPO3288	Microcystis aeruginosa	Species	Microcystaceae	Bacteria	n.a.	n.a.	n.a.	PMID[24868986]
NPO3288	Microcystis aeruginosa	Species	Microcystaceae	Bacteria	n.a.	n.a.	n.a.	PMID[29405714]
NPO3288	Microcystis aeruginosa	Species	Microcystaceae	Bacteria	Bloom	n.a.	n.a.	PMID[29847132]
NPO3288	Microcystis aeruginosa	Species	Microcystaceae	Bacteria	n.a.	n.a.	n.a.	PMID[9249979]
NPO3288	Microcystis aeruginosa	Species	Microcystaceae	Bacteria	n.a.	n.a.	n.a.	PMID[9842728]
NPO3288	Microcystis aeruginosa	Species	Microcystaceae	Bacteria	n.a.	n.a.	n.a.	Database[Title]
NPO3288	Microcystis aeruginosa	Species	Microcystaceae	Bacteria	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	2

Activity Type	# Activity
Others	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT2	Others	Unspecified		IC50	=	1100.0	nM	PMID[519167]
NPT2	Others	Unspecified		IC50	=	2800.0	nM	PMID[519167]

☑ 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 NPC219350 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	243
0.1-0.2	1462
0.2-0.3	8699
0.3-0.4	9914
0.4-0.5	18347
0.5-0.6	3444
0.6-0.7	388
0.7-0.8	176
0.8-0.85	15
0.85-0.9	1
0.9-0.95	3
0.95-1	5

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC194699
0.9786	High Similarity	NPC469442
0.9786	High Similarity	NPC277306
0.9683	High Similarity	NPC25539
0.9459	High Similarity	NPC469443
0.9162	High Similarity	NPC220060
0.9115	High Similarity	NPC469444
0.8974	High Similarity	NPC469445
0.8446	Intermediate Similarity	NPC473371
0.8421	Intermediate Similarity	NPC102959
0.8396	Intermediate Similarity	NPC473404
0.8377	Intermediate Similarity	NPC60516
0.8247	Intermediate Similarity	NPC302715
0.8187	Intermediate Similarity	NPC51047
0.8182	Intermediate Similarity	NPC473450
0.8182	Intermediate Similarity	NPC477551
0.8173	Intermediate Similarity	NPC477550
0.8173	Intermediate Similarity	NPC477552
0.8093	Intermediate Similarity	NPC61332
0.8093	Intermediate Similarity	NPC240130
0.7968	Intermediate Similarity	NPC46009
0.7959	Intermediate Similarity	NPC248822
0.7959	Intermediate Similarity	NPC470728
0.7923	Intermediate Similarity	NPC1390
0.7923	Intermediate Similarity	NPC62104
0.7895	Intermediate Similarity	NPC50016
0.7884	Intermediate Similarity	NPC273755
0.7812	Intermediate Similarity	NPC45037
0.7778	Intermediate Similarity	NPC473378
0.7778	Intermediate Similarity	NPC475123
0.7778	Intermediate Similarity	NPC473407
0.7778	Intermediate Similarity	NPC475204
0.7754	Intermediate Similarity	NPC22883
0.7754	Intermediate Similarity	NPC210377
0.7754	Intermediate Similarity	NPC5719
0.7754	Intermediate Similarity	NPC217804
0.7723	Intermediate Similarity	NPC323662
0.7696	Intermediate Similarity	NPC306804
0.7672	Intermediate Similarity	NPC63040
0.7656	Intermediate Similarity	NPC473354
0.7619	Intermediate Similarity	NPC15068
0.7614	Intermediate Similarity	NPC299806
0.7612	Intermediate Similarity	NPC328763
0.7592	Intermediate Similarity	NPC471568
0.7592	Intermediate Similarity	NPC196091
0.7592	Intermediate Similarity	NPC198254
0.7592	Intermediate Similarity	NPC473693
0.7592	Intermediate Similarity	NPC274198
0.7579	Intermediate Similarity	NPC107938
0.7579	Intermediate Similarity	NPC294516
0.7566	Intermediate Similarity	NPC472923
0.7552	Intermediate Similarity	NPC230611
0.7547	Intermediate Similarity	NPC326027
0.7539	Intermediate Similarity	NPC186617
0.7538	Intermediate Similarity	NPC194671
0.7538	Intermediate Similarity	NPC269750
0.7538	Intermediate Similarity	NPC94862
0.7536	Intermediate Similarity	NPC326333
0.7513	Intermediate Similarity	NPC137627
0.75	Intermediate Similarity	NPC81845
0.75	Intermediate Similarity	NPC276506
0.75	Intermediate Similarity	NPC40234
0.7475	Intermediate Similarity	NPC294951
0.7474	Intermediate Similarity	NPC473402
0.7474	Intermediate Similarity	NPC471165
0.7474	Intermediate Similarity	NPC279871
0.7474	Intermediate Similarity	NPC26108
0.7462	Intermediate Similarity	NPC476321
0.7448	Intermediate Similarity	NPC280022
0.7436	Intermediate Similarity	NPC196243
0.7424	Intermediate Similarity	NPC471526
0.7409	Intermediate Similarity	NPC151030
0.7409	Intermediate Similarity	NPC269383
0.7406	Intermediate Similarity	NPC295795
0.7387	Intermediate Similarity	NPC471048
0.7387	Intermediate Similarity	NPC471049
0.7387	Intermediate Similarity	NPC471050
0.7385	Intermediate Similarity	NPC159767
0.7385	Intermediate Similarity	NPC476227
0.7385	Intermediate Similarity	NPC155506
0.736	Intermediate Similarity	NPC475421
0.7333	Intermediate Similarity	NPC248670
0.7323	Intermediate Similarity	NPC271958
0.7323	Intermediate Similarity	NPC45112
0.7323	Intermediate Similarity	NPC263507
0.7323	Intermediate Similarity	NPC134413
0.7317	Intermediate Similarity	NPC477638
0.7317	Intermediate Similarity	NPC477632
0.7306	Intermediate Similarity	NPC209463
0.7292	Intermediate Similarity	NPC63931
0.7291	Intermediate Similarity	NPC163961
0.7291	Intermediate Similarity	NPC473305
0.7273	Intermediate Similarity	NPC97526
0.7273	Intermediate Similarity	NPC119652
0.7268	Intermediate Similarity	NPC129486
0.725	Intermediate Similarity	NPC470903
0.725	Intermediate Similarity	NPC167763
0.725	Intermediate Similarity	NPC470112
0.7245	Intermediate Similarity	NPC49315
0.7245	Intermediate Similarity	NPC475532
0.7236	Intermediate Similarity	NPC153554
0.7225	Intermediate Similarity	NPC469243
0.722	Intermediate Similarity	NPC477631
0.7208	Intermediate Similarity	NPC165285
0.7208	Intermediate Similarity	NPC17698
0.7206	Intermediate Similarity	NPC477636
0.7196	Intermediate Similarity	NPC473580
0.7184	Intermediate Similarity	NPC65714
0.7181	Intermediate Similarity	NPC473341
0.7178	Intermediate Similarity	NPC315542
0.7165	Intermediate Similarity	NPC254700
0.7164	Intermediate Similarity	NPC86678
0.7135	Intermediate Similarity	NPC471527
0.7135	Intermediate Similarity	NPC475544
0.7128	Intermediate Similarity	NPC473502
0.7113	Intermediate Similarity	NPC223207
0.7083	Intermediate Similarity	NPC319320
0.7083	Intermediate Similarity	NPC287757
0.7081	Intermediate Similarity	NPC471592
0.7077	Intermediate Similarity	NPC304074
0.7077	Intermediate Similarity	NPC471771
0.7077	Intermediate Similarity	NPC290755
0.707	Intermediate Similarity	NPC478005
0.7065	Intermediate Similarity	NPC475564
0.7065	Intermediate Similarity	NPC170302
0.7065	Intermediate Similarity	NPC475409
0.7062	Intermediate Similarity	NPC242728
0.7049	Intermediate Similarity	NPC163392
0.7049	Intermediate Similarity	NPC239762
0.7039	Intermediate Similarity	NPC64140
0.7039	Intermediate Similarity	NPC174122
0.7035	Intermediate Similarity	NPC227778
0.7033	Intermediate Similarity	NPC477639
0.7024	Intermediate Similarity	NPC4910
0.702	Intermediate Similarity	NPC89831
0.701	Intermediate Similarity	NPC138083
0.7005	Intermediate Similarity	NPC477526
0.699	Remote Similarity	NPC234069
0.6984	Remote Similarity	NPC324081
0.6965	Remote Similarity	NPC473546
0.6951	Remote Similarity	NPC478007
0.6947	Remote Similarity	NPC300443
0.6942	Remote Similarity	NPC96275
0.6911	Remote Similarity	NPC262166
0.6905	Remote Similarity	NPC184933
0.6905	Remote Similarity	NPC59827
0.6904	Remote Similarity	NPC61004
0.6889	Remote Similarity	NPC478008
0.6875	Remote Similarity	NPC274268
0.6872	Remote Similarity	NPC114806
0.6872	Remote Similarity	NPC149962
0.6866	Remote Similarity	NPC158277
0.6866	Remote Similarity	NPC164608
0.6865	Remote Similarity	NPC48202
0.6863	Remote Similarity	NPC477637
0.6862	Remote Similarity	NPC81026
0.686	Remote Similarity	NPC329731
0.6857	Remote Similarity	NPC314083
0.685	Remote Similarity	NPC328494
0.6845	Remote Similarity	NPC235194
0.6842	Remote Similarity	NPC2501
0.684	Remote Similarity	NPC144314
0.6839	Remote Similarity	NPC476268
0.6823	Remote Similarity	NPC122590
0.6821	Remote Similarity	NPC24617
0.6814	Remote Similarity	NPC32064
0.6812	Remote Similarity	NPC276120
0.6809	Remote Similarity	NPC266741
0.6808	Remote Similarity	NPC477527
0.6808	Remote Similarity	NPC50548
0.6802	Remote Similarity	NPC471052
0.6802	Remote Similarity	NPC471053
0.6802	Remote Similarity	NPC471051
0.6792	Remote Similarity	NPC329295
0.6791	Remote Similarity	NPC91953
0.6791	Remote Similarity	NPC168861
0.6788	Remote Similarity	NPC39431
0.6784	Remote Similarity	NPC302597
0.6776	Remote Similarity	NPC123859
0.6769	Remote Similarity	NPC56635
0.6763	Remote Similarity	NPC319774
0.6753	Remote Similarity	NPC244509
0.675	Remote Similarity	NPC314743
0.675	Remote Similarity	NPC66490
0.6746	Remote Similarity	NPC246591
0.6738	Remote Similarity	NPC197921
0.6737	Remote Similarity	NPC135121
0.6736	Remote Similarity	NPC56685
0.6735	Remote Similarity	NPC244336
0.672	Remote Similarity	NPC477217
0.672	Remote Similarity	NPC201244
0.6702	Remote Similarity	NPC469360
0.6684	Remote Similarity	NPC297145
0.6684	Remote Similarity	NPC214988
0.6684	Remote Similarity	NPC197743
0.6667	Remote Similarity	NPC6570
0.6667	Remote Similarity	NPC52748
0.6667	Remote Similarity	NPC80514
0.6667	Remote Similarity	NPC127741
0.6649	Remote Similarity	NPC5194

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 NPC219350 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	480
0.2-0.3	980
0.3-0.4	2190
0.4-0.5	3217
0.5-0.6	1955
0.6-0.7	177
0.7-0.8	11
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
0.7526	Intermediate Similarity	NPD8303	Discontinued
0.7323	Intermediate Similarity	NPD7959	Clinical (unspecified phase)
0.7286	Intermediate Similarity	NPD8014	Clinical (unspecified phase)
0.7268	Intermediate Similarity	NPD7484	Phase 3
0.7268	Intermediate Similarity	NPD7485	Phase 3
0.7231	Intermediate Similarity	NPD7608	Discontinued
0.7166	Intermediate Similarity	NPD5348	Clinical (unspecified phase)
0.7135	Intermediate Similarity	NPD3465	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD8019	Approved
0.7083	Intermediate Similarity	NPD4018	Clinical (unspecified phase)
0.7067	Intermediate Similarity	NPD6312	Discontinued
0.7037	Intermediate Similarity	NPD6689	Clinical (unspecified phase)
0.7026	Intermediate Similarity	NPD8031	Discontinued
0.701	Intermediate Similarity	NPD6853	Approved
0.701	Intermediate Similarity	NPD6851	Approved
0.6995	Remote Similarity	NPD3936	Clinical (unspecified phase)
0.6995	Remote Similarity	NPD7495	Discontinued
0.6911	Remote Similarity	NPD7523	Phase 3
0.6895	Remote Similarity	NPD6419	Discontinued
0.686	Remote Similarity	NPD6089	Clinical (unspecified phase)
0.6837	Remote Similarity	NPD8163	Clinical (unspecified phase)
0.6837	Remote Similarity	NPD8162	Phase 2
0.6837	Remote Similarity	NPD4971	Clinical (unspecified phase)
0.6823	Remote Similarity	NPD7131	Phase 3
0.6814	Remote Similarity	NPD6297	Approved
0.6798	Remote Similarity	NPD5095	Phase 3
0.6798	Remote Similarity	NPD3933	Discontinued
0.6798	Remote Similarity	NPD5096	Phase 3
0.6791	Remote Similarity	NPD8076	Discontinued
0.6779	Remote Similarity	NPD3857	Clinical (unspecified phase)
0.6769	Remote Similarity	NPD7118	Clinical (unspecified phase)
0.6755	Remote Similarity	NPD6681	Discovery
0.6698	Remote Similarity	NPD7811	Phase 3
0.6698	Remote Similarity	NPD7810	Phase 3
0.6684	Remote Similarity	NPD2541	Clinical (unspecified phase)
0.6598	Remote Similarity	NPD6078	Clinical (unspecified phase)
0.6595	Remote Similarity	NPD5745	Approved
0.6591	Remote Similarity	NPD6905	Phase 2
0.6588	Remote Similarity	NPD4157	Discontinued
0.6587	Remote Similarity	NPD7132	Clinical (unspecified phase)
0.6566	Remote Similarity	NPD5356	Approved
0.6566	Remote Similarity	NPD5355	Approved
0.6561	Remote Similarity	NPD2239	Approved
0.6561	Remote Similarity	NPD2240	Approved
0.6561	Remote Similarity	NPD3175	Clinical (unspecified phase)
0.6545	Remote Similarity	NPD2976	Clinical (unspecified phase)
0.6538	Remote Similarity	NPD5192	Clinical (unspecified phase)
0.6531	Remote Similarity	NPD6670	Clinical (unspecified phase)
0.653	Remote Similarity	NPD6863	Phase 2
0.6526	Remote Similarity	NPD7978	Discontinued
0.6524	Remote Similarity	NPD5946	Clinical (unspecified phase)
0.6513	Remote Similarity	NPD4186	Clinical (unspecified phase)
0.65	Remote Similarity	NPD5152	Clinical (unspecified phase)
0.6486	Remote Similarity	NPD5746	Approved
0.6486	Remote Similarity	NPD3136	Phase 2
0.6462	Remote Similarity	NPD3536	Discontinued
0.6456	Remote Similarity	NPD3366	Approved
0.6455	Remote Similarity	NPD6901	Phase 3
0.645	Remote Similarity	NPD7972	Discontinued
0.6438	Remote Similarity	NPD3602	Clinical (unspecified phase)
0.6429	Remote Similarity	NPD4731	Phase 3
0.6422	Remote Similarity	NPD6107	Approved
0.6418	Remote Similarity	NPD5967	Approved
0.6417	Remote Similarity	NPD1423	Approved
0.6402	Remote Similarity	NPD7617	Discontinued
0.6377	Remote Similarity	NPD5200	Clinical (unspecified phase)
0.6373	Remote Similarity	NPD1416	Approved
0.6368	Remote Similarity	NPD6237	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD5542	Phase 2
0.6359	Remote Similarity	NPD5308	Clinical (unspecified phase)
0.6359	Remote Similarity	NPD4588	Clinical (unspecified phase)
0.6355	Remote Similarity	NPD8070	Approved
0.635	Remote Similarity	NPD6677	Suspended
0.6345	Remote Similarity	NPD6390	Discontinued
0.6343	Remote Similarity	NPD5165	Clinical (unspecified phase)
0.6338	Remote Similarity	NPD6967	Phase 2
0.6336	Remote Similarity	NPD7805	Phase 3
0.633	Remote Similarity	NPD2245	Discovery
0.6318	Remote Similarity	NPD4227	Discontinued
0.6316	Remote Similarity	NPD4782	Clinical (unspecified phase)
0.6308	Remote Similarity	NPD5309	Clinical (unspecified phase)
0.6306	Remote Similarity	NPD6510	Phase 1
0.6306	Remote Similarity	NPD6511	Phase 1
0.6291	Remote Similarity	NPD6556	Clinical (unspecified phase)
0.6289	Remote Similarity	NPD2459	Approved
0.6289	Remote Similarity	NPD2460	Phase 3
0.6289	Remote Similarity	NPD2458	Approved
0.6286	Remote Similarity	NPD5557	Phase 1
0.6284	Remote Similarity	NPD4413	Clinical (unspecified phase)
0.6277	Remote Similarity	NPD3056	Clinical (unspecified phase)
0.6276	Remote Similarity	NPD8290	Clinical (unspecified phase)
0.6271	Remote Similarity	NPD5567	Approved
0.6269	Remote Similarity	NPD469	Approved
0.6269	Remote Similarity	NPD470	Approved
0.6268	Remote Similarity	NPD3909	Discontinued
0.6263	Remote Similarity	NPD4757	Clinical (unspecified phase)
0.6263	Remote Similarity	NPD2186	Approved
0.6262	Remote Similarity	NPD5649	Clinical (unspecified phase)
0.6256	Remote Similarity	NPD1662	Clinical (unspecified phase)
0.625	Remote Similarity	NPD3451	Clinical (unspecified phase)
0.625	Remote Similarity	NPD5910	Clinical (unspecified phase)
0.625	Remote Similarity	NPD2661	Clinical (unspecified phase)
0.6237	Remote Similarity	NPD7596	Clinical (unspecified phase)
0.623	Remote Similarity	NPD3054	Approved
0.623	Remote Similarity	NPD3052	Approved
0.6218	Remote Similarity	NPD1725	Approved
0.6214	Remote Similarity	NPD2904	Discontinued
0.6212	Remote Similarity	NPD3985	Discontinued
0.6212	Remote Similarity	NPD3157	Approved
0.6212	Remote Similarity	NPD3158	Phase 1
0.6211	Remote Similarity	NPD4917	Discontinued
0.6211	Remote Similarity	NPD3591	Approved
0.6211	Remote Similarity	NPD3592	Approved
0.6209	Remote Similarity	NPD3885	Approved
0.6207	Remote Similarity	NPD5773	Approved
0.6207	Remote Similarity	NPD5772	Approved
0.6205	Remote Similarity	NPD3804	Discontinued
0.6205	Remote Similarity	NPD6860	Clinical (unspecified phase)
0.62	Remote Similarity	NPD3686	Approved
0.62	Remote Similarity	NPD5267	Discontinued
0.62	Remote Similarity	NPD3687	Approved
0.6197	Remote Similarity	NPD1381	Clinical (unspecified phase)
0.6195	Remote Similarity	NPD4064	Discontinued
0.6195	Remote Similarity	NPD5218	Approved
0.6195	Remote Similarity	NPD5219	Approved
0.6193	Remote Similarity	NPD3819	Phase 2
0.6193	Remote Similarity	NPD3281	Clinical (unspecified phase)
0.6188	Remote Similarity	NPD4424	Discontinued
0.6186	Remote Similarity	NPD3656	Approved
0.6182	Remote Similarity	NPD7667	Clinical (unspecified phase)
0.6182	Remote Similarity	NPD3964	Approved
0.6182	Remote Similarity	NPD3659	Discontinued
0.6181	Remote Similarity	NPD7527	Clinical (unspecified phase)
0.6181	Remote Similarity	NPD7526	Approved
0.6181	Remote Similarity	NPD7303	Discontinued
0.6181	Remote Similarity	NPD52	Approved
0.6181	Remote Similarity	NPD7613	Discontinued
0.6179	Remote Similarity	NPD7792	Phase 1
0.6176	Remote Similarity	NPD2097	Approved
0.6175	Remote Similarity	NPD6377	Clinical (unspecified phase)
0.6173	Remote Similarity	NPD7066	Clinical (unspecified phase)
0.6171	Remote Similarity	NPD7565	Approved
0.6169	Remote Similarity	NPD6056	Approved
0.6169	Remote Similarity	NPD6057	Approved
0.6168	Remote Similarity	NPD8064	Clinical (unspecified phase)
0.6168	Remote Similarity	NPD7280	Phase 3
0.6168	Remote Similarity	NPD7281	Phase 3
0.6165	Remote Similarity	NPD8245	Clinical (unspecified phase)
0.6161	Remote Similarity	NPD42	Phase 2
0.6161	Remote Similarity	NPD5313	Approved
0.6161	Remote Similarity	NPD6042	Phase 2
0.6161	Remote Similarity	NPD5312	Approved
0.6158	Remote Similarity	NPD2515	Approved
0.6158	Remote Similarity	NPD3007	Approved
0.6157	Remote Similarity	NPD3863	Clinical (unspecified phase)
0.6154	Remote Similarity	NPD5650	Approved
0.6154	Remote Similarity	NPD5651	Approved
0.6154	Remote Similarity	NPD5341	Clinical (unspecified phase)
0.6154	Remote Similarity	NPD6034	Phase 2
0.6154	Remote Similarity	NPD4652	Approved
0.6154	Remote Similarity	NPD5652	Approved
0.6143	Remote Similarity	NPD5605	Phase 2
0.6138	Remote Similarity	NPD3166	Approved
0.6138	Remote Similarity	NPD3165	Approved
0.6138	Remote Similarity	NPD3164	Approved
0.6138	Remote Similarity	NPD3167	Approved
0.6136	Remote Similarity	NPD7669	Phase 3
0.6135	Remote Similarity	NPD3365	Discontinued
0.6132	Remote Similarity	NPD5485	Approved
0.6132	Remote Similarity	NPD7574	Phase 2
0.6132	Remote Similarity	NPD5484	Approved
0.6131	Remote Similarity	NPD2874	Phase 2
0.6131	Remote Similarity	NPD1771	Clinical (unspecified phase)
0.6127	Remote Similarity	NPD6668	Clinical (unspecified phase)
0.6126	Remote Similarity	NPD4791	Clinical (unspecified phase)
0.6124	Remote Similarity	NPD5137	Approved
0.6122	Remote Similarity	NPD4162	Approved
0.6122	Remote Similarity	NPD4487	Clinical (unspecified phase)
0.6121	Remote Similarity	NPD2166	Phase 3
0.6119	Remote Similarity	NPD4124	Clinical (unspecified phase)
0.6117	Remote Similarity	NPD2098	Approved
0.6117	Remote Similarity	NPD454	Approved
0.6117	Remote Similarity	NPD4521	Clinical (unspecified phase)
0.6111	Remote Similarity	NPD5295	Discontinued
0.6108	Remote Similarity	NPD6072	Discontinued
0.6108	Remote Similarity	NPD3274	Phase 2
0.6108	Remote Similarity	NPD2513	Approved
0.6103	Remote Similarity	NPD6809	Clinical (unspecified phase)
0.6098	Remote Similarity	NPD2379	Clinical (unspecified phase)
0.6096	Remote Similarity	NPD1819	Approved
0.6096	Remote Similarity	NPD1817	Approved
0.6096	Remote Similarity	NPD8027	Approved
0.6096	Remote Similarity	NPD1818	Approved
0.6096	Remote Similarity	NPD1820	Approved
0.6091	Remote Similarity	NPD5984	Phase 2
0.6091	Remote Similarity	NPD6181	Discontinued
0.6089	Remote Similarity	NPD2498	Approved
0.6089	Remote Similarity	NPD3106	Clinical (unspecified phase)
0.6087	Remote Similarity	NPD6315	Phase 2
0.608	Remote Similarity	NPD6088	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