NPASS Compound

Structure

NPC24990 OpenBabel07101718322D 39 43 0 0 1 0 0 0 0 0999 V2000 3.5984 3.1659 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9881 0.4783 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.7340 2.1771 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.7506 1.1772 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8599 2.6627 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8929 0.6630 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0022 2.1485 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3477 0.3107 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2699 0.6972 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1611 0.6343 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9600 3.6378 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0655 2.0150 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5335 -0.1414 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8195 2.5387 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 4.0188 1.1486 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5518 0.9162 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.2869 1.1200 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8005 2.5150 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9227 0.2500 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.4019 3.5977 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3048 2.7379 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8987 1.9641 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4666 0.3813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9660 3.1832 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4745 1.6472 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1443 0.5327 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5009 3.4944 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -0.5926 3.4932 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -0.8127 1.4112 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 1.9384 0.6822 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 0.3656 0.3023 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 2.4806 2.2067 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -1.8986 1.9752 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.8582 -0.5388 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.6513 3.9114 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.9043 1.9933 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.0658 0.0918 0.0000 S 0 0 0 0 0 0 0 0 0 0 0 0 0.8087 2.6842 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 2 37 1 0 0 0 0 3 4 2 0 0 0 0 3 5 1 0 0 0 0 4 6 1 0 0 0 0 5 7 2 0 0 0 0 6 15 2 0 0 0 0 7 15 1 0 0 0 0 8 9 1 0 0 0 0 9 37 1 0 0 0 0 10 15 1 0 0 0 0 11 20 1 0 0 0 0 11 27 1 0 0 0 0 12 18 2 0 0 0 0 12 38 1 0 0 0 0 13 39 1 0 0 0 0 14 1 1 1 0 0 0 14 21 1 0 0 0 0 14 36 1 0 0 0 0 16 8 1 6 0 0 0 16 26 1 0 0 0 0 16 29 1 0 0 0 0 17 10 1 6 0 0 0 17 25 1 0 0 0 0 17 30 1 0 0 0 0 18 22 1 0 0 0 0 18 28 1 0 0 0 0 19 13 1 6 0 0 0 19 23 1 0 0 0 0 19 31 1 0 0 0 0 20 28 2 0 0 0 0 20 38 1 0 0 0 0 21 24 1 6 0 0 0 21 32 1 0 0 0 0 22 29 2 3 0 0 0 22 33 1 0 0 0 0 23 30 2 3 0 0 0 23 34 1 0 0 0 0 24 27 2 3 0 0 0 24 35 1 0 0 0 0 25 32 2 0 0 0 0 25 36 1 0 0 0 0 26 31 2 0 0 0 0 26 39 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	586.15
Volume:	545.774
LogP:	1.838
LogD:	3.304
LogS:	-3.083
# Rotatable Bonds:	5
TPSA:	145.23
# H-Bond Aceptor:	10
# H-Bond Donor:	4
# Rings:	5
# Heavy Atoms:	13

MedChem Properties

QED Drug-Likeness Score:	0.352
Synthetic Accessibility Score:	6.746
Fsp3:	0.423
Lipinski Rule-of-5:	Accepted
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:	-5.529
MDCK Permeability:	1.2018550478387624e-05
Pgp-inhibitor:	0.001
Pgp-substrate:	0.973
Human Intestinal Absorption (HIA):	0.028
20% Bioavailability (F20%):	0.004
30% Bioavailability (F30%):	0.014

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.227
Plasma Protein Binding (PPB):	91.2652359008789%
Volume Distribution (VD):	2.615
Pgp-substrate:	8.1427640914917%

ADMET: Metabolism

CYP1A2-inhibitor:	0.091
CYP1A2-substrate:	0.108
CYP2C19-inhibitor:	0.241
CYP2C19-substrate:	0.192
CYP2C9-inhibitor:	0.319
CYP2C9-substrate:	0.314
CYP2D6-inhibitor:	0.005
CYP2D6-substrate:	0.137
CYP3A4-inhibitor:	0.218
CYP3A4-substrate:	0.801

ADMET: Excretion

Clearance (CL):	2.189
Half-life (T1/2):	0.318

ADMET: Toxicity

hERG Blockers:	0.169
Human Hepatotoxicity (H-HT):	0.998
Drug-inuced Liver Injury (DILI):	0.984
AMES Toxicity:	0.015
Rat Oral Acute Toxicity:	0.115
Maximum Recommended Daily Dose:	0.975
Skin Sensitization:	0.114
Carcinogencity:	0.081
Eye Corrosion:	0.003
Eye Irritation:	0.005
Respiratory Toxicity:	0.955

Download Data

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

Natural Product: NPC24990

Natural Product ID:	NPC24990
*Common Name:**	Aerucyclamide D
IUPAC Name:	n.a.
Synonyms:	Aerucyclamide D
Standard InCHIKey:	MLBROOJXUZKDHY-PKPICYNOSA-N
Standard InCHI:	InChI=1S/C26H30N6O4S3/c1-14-21-24(35)27-11-20-28-18(12-38-20)22(33)29-16(8-9-37-2)26-31-19(13-39-26)23(34)30-17(25(32-21)36-14)10-15-6-4-3-5-7-15/h3-7,12,14,16-17,19,21H,8-11,13H2,1-2H3,(H,27,35)(H,29,33)(H,30,34)/t14-,16+,17+,19+,21+/m1/s1
SMILES:	C[C@@H]1[C@H]2C(=NCc3nc(cs3)C(=N[C@@H](CCSC)C3=N[C@@H](CS3)C(=N[C@@H](Cc3ccccc3)C(=N2)O1)O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL584196
PubChem CID:	25156432
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
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.	n.a.	n.a.	PMID[12141855]
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[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	3

Activity Type	# Activity
Cell Line	1
Organism	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT839	Cell Line	L6	Rattus norvegicus	IC50	>	153000.0	nM	PMID[566058]
NPT485	Organism	Plasmodium falciparum (isolate K1 / Thailand)	Plasmodium falciparum K1	IC50	=	6300.0	nM	PMID[566058]
NPT844	Organism	Trypanosoma brucei rhodesiense	Trypanosoma brucei rhodesiense	IC50	=	50100.0	nM	PMID[566058]

☑ 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 NPC24990 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	236
0.1-0.2	2068
0.2-0.3	14319
0.3-0.4	18733
0.4-0.5	5786
0.5-0.6	1455
0.6-0.7	73
0.7-0.8	15
0.8-0.85	2
0.85-0.9	1
0.9-0.95	8
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9259	High Similarity	NPC25316
0.9259	High Similarity	NPC263485
0.9259	High Similarity	NPC229160
0.9198	High Similarity	NPC475330
0.9141	High Similarity	NPC174652
0.9136	High Similarity	NPC161242
0.9018	High Similarity	NPC476080
0.9018	High Similarity	NPC475534
0.8598	High Similarity	NPC476103
0.8182	Intermediate Similarity	NPC329961
0.8182	Intermediate Similarity	NPC122427
0.7989	Intermediate Similarity	NPC165538
0.7753	Intermediate Similarity	NPC96016
0.7556	Intermediate Similarity	NPC49051
0.7461	Intermediate Similarity	NPC475350
0.7461	Intermediate Similarity	NPC145178
0.7461	Intermediate Similarity	NPC14877
0.7347	Intermediate Similarity	NPC251036
0.7338	Intermediate Similarity	NPC267605
0.7158	Intermediate Similarity	NPC161143
0.7152	Intermediate Similarity	NPC89592
0.7143	Intermediate Similarity	NPC239660
0.7143	Intermediate Similarity	NPC106235
0.7081	Intermediate Similarity	NPC74917
0.7037	Intermediate Similarity	NPC120917
0.7033	Intermediate Similarity	NPC469858
0.7032	Intermediate Similarity	NPC135558
0.6899	Remote Similarity	NPC51692
0.6882	Remote Similarity	NPC319751
0.6865	Remote Similarity	NPC249662
0.6805	Remote Similarity	NPC469801
0.6802	Remote Similarity	NPC473398
0.6763	Remote Similarity	NPC119481
0.6682	Remote Similarity	NPC475196
0.66	Remote Similarity	NPC75498
0.6592	Remote Similarity	NPC315252
0.6557	Remote Similarity	NPC475920
0.6514	Remote Similarity	NPC283783
0.6478	Remote Similarity	NPC214375
0.6437	Remote Similarity	NPC475390
0.6432	Remote Similarity	NPC97078
0.6432	Remote Similarity	NPC101980
0.6432	Remote Similarity	NPC470146
0.64	Remote Similarity	NPC470824
0.6383	Remote Similarity	NPC318930
0.6383	Remote Similarity	NPC317362
0.6381	Remote Similarity	NPC79386
0.6359	Remote Similarity	NPC188104
0.6341	Remote Similarity	NPC475568
0.6325	Remote Similarity	NPC475604
0.6307	Remote Similarity	NPC474069
0.6296	Remote Similarity	NPC317725
0.6296	Remote Similarity	NPC326407
0.6257	Remote Similarity	NPC157194
0.6257	Remote Similarity	NPC474070
0.6257	Remote Similarity	NPC474079
0.6257	Remote Similarity	NPC475683
0.6257	Remote Similarity	NPC474102
0.6257	Remote Similarity	NPC21449
0.6257	Remote Similarity	NPC474080
0.6244	Remote Similarity	NPC257511
0.6243	Remote Similarity	NPC268063
0.6243	Remote Similarity	NPC224609
0.6224	Remote Similarity	NPC238242
0.6208	Remote Similarity	NPC314254
0.6208	Remote Similarity	NPC313966
0.6201	Remote Similarity	NPC474068
0.6201	Remote Similarity	NPC474064
0.6201	Remote Similarity	NPC474103
0.6201	Remote Similarity	NPC82436
0.6196	Remote Similarity	NPC231110
0.6188	Remote Similarity	NPC474090
0.6188	Remote Similarity	NPC154873
0.6188	Remote Similarity	NPC163147
0.6188	Remote Similarity	NPC109498
0.6188	Remote Similarity	NPC32583
0.6188	Remote Similarity	NPC61667
0.6188	Remote Similarity	NPC45576
0.6188	Remote Similarity	NPC252616
0.6162	Remote Similarity	NPC522
0.6162	Remote Similarity	NPC56058
0.6162	Remote Similarity	NPC312887
0.6141	Remote Similarity	NPC127775
0.6138	Remote Similarity	NPC164006
0.6133	Remote Similarity	NPC185665
0.6133	Remote Similarity	NPC475737
0.6133	Remote Similarity	NPC474067
0.6133	Remote Similarity	NPC474094
0.6124	Remote Similarity	NPC128237
0.6124	Remote Similarity	NPC83790
0.6103	Remote Similarity	NPC163055
0.6099	Remote Similarity	NPC206724
0.6099	Remote Similarity	NPC474515
0.6096	Remote Similarity	NPC476118
0.6092	Remote Similarity	NPC89489
0.6067	Remote Similarity	NPC190329
0.6061	Remote Similarity	NPC478030
0.6054	Remote Similarity	NPC52587
0.6054	Remote Similarity	NPC474538
0.6033	Remote Similarity	NPC212214
0.6033	Remote Similarity	NPC202591
0.601	Remote Similarity	NPC472122
0.601	Remote Similarity	NPC24594
0.6	Remote Similarity	NPC21126
0.5979	Remote Similarity	NPC132662
0.5979	Remote Similarity	NPC211997
0.5979	Remote Similarity	NPC248454
0.5965	Remote Similarity	NPC300315
0.5941	Remote Similarity	NPC75609
0.5941	Remote Similarity	NPC140284
0.5938	Remote Similarity	NPC158129
0.5936	Remote Similarity	NPC237219
0.5934	Remote Similarity	NPC7817
0.5934	Remote Similarity	NPC475168
0.5928	Remote Similarity	NPC252878
0.5928	Remote Similarity	NPC134586
0.5922	Remote Similarity	NPC471680
0.5918	Remote Similarity	NPC472105
0.5918	Remote Similarity	NPC187827
0.5912	Remote Similarity	NPC105717
0.5907	Remote Similarity	NPC34508
0.5897	Remote Similarity	NPC326575
0.5895	Remote Similarity	NPC475554
0.5893	Remote Similarity	NPC46427
0.5885	Remote Similarity	NPC143325
0.5871	Remote Similarity	NPC46413
0.5868	Remote Similarity	NPC86966
0.5867	Remote Similarity	NPC133261
0.5867	Remote Similarity	NPC270009
0.586	Remote Similarity	NPC470507
0.5859	Remote Similarity	NPC139291
0.5859	Remote Similarity	NPC472108
0.5859	Remote Similarity	NPC472109
0.5859	Remote Similarity	NPC472110
0.5856	Remote Similarity	NPC477556
0.5842	Remote Similarity	NPC311276
0.5838	Remote Similarity	NPC168486
0.5838	Remote Similarity	NPC222592
0.5838	Remote Similarity	NPC470902
0.5821	Remote Similarity	NPC4910
0.5821	Remote Similarity	NPC329731
0.5819	Remote Similarity	NPC477557
0.5819	Remote Similarity	NPC103268
0.581	Remote Similarity	NPC138562
0.5808	Remote Similarity	NPC112823
0.5808	Remote Similarity	NPC476990
0.5806	Remote Similarity	NPC161108
0.5796	Remote Similarity	NPC113326
0.5796	Remote Similarity	NPC224610
0.5796	Remote Similarity	NPC194390
0.5796	Remote Similarity	NPC88267
0.5795	Remote Similarity	NPC469938
0.5789	Remote Similarity	NPC273714
0.5787	Remote Similarity	NPC472443
0.5784	Remote Similarity	NPC148592
0.5784	Remote Similarity	NPC286551
0.5779	Remote Similarity	NPC472444
0.5774	Remote Similarity	NPC324702
0.5774	Remote Similarity	NPC202521
0.5769	Remote Similarity	NPC18487
0.5756	Remote Similarity	NPC151779
0.5753	Remote Similarity	NPC49195
0.5753	Remote Similarity	NPC14101
0.5746	Remote Similarity	NPC88121
0.5746	Remote Similarity	NPC322878
0.5745	Remote Similarity	NPC141353
0.5745	Remote Similarity	NPC285469
0.5736	Remote Similarity	NPC293472
0.5735	Remote Similarity	NPC243716
0.573	Remote Similarity	NPC37548
0.5729	Remote Similarity	NPC192270
0.5728	Remote Similarity	NPC59827
0.5728	Remote Similarity	NPC184933
0.5728	Remote Similarity	NPC294693
0.5723	Remote Similarity	NPC169328
0.5722	Remote Similarity	NPC468984
0.5722	Remote Similarity	NPC161069
0.5721	Remote Similarity	NPC62510
0.5721	Remote Similarity	NPC478141
0.5714	Remote Similarity	NPC477061
0.5714	Remote Similarity	NPC45777
0.5708	Remote Similarity	NPC214827
0.5708	Remote Similarity	NPC314930
0.5706	Remote Similarity	NPC6975
0.5703	Remote Similarity	NPC315061
0.5699	Remote Similarity	NPC160105
0.5691	Remote Similarity	NPC476978
0.5691	Remote Similarity	NPC471458
0.5691	Remote Similarity	NPC315283
0.5691	Remote Similarity	NPC314388
0.5689	Remote Similarity	NPC237420
0.5689	Remote Similarity	NPC310467
0.5686	Remote Similarity	NPC315411
0.5678	Remote Similarity	NPC164228
0.5674	Remote Similarity	NPC471264
0.5674	Remote Similarity	NPC478158
0.5674	Remote Similarity	NPC471265
0.5672	Remote Similarity	NPC320394
0.5671	Remote Similarity	NPC1986
0.5671	Remote Similarity	NPC474544

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 NPC24990 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	141
0.1-0.2	545
0.2-0.3	963
0.3-0.4	2190
0.4-0.5	4351
0.5-0.6	918
0.6-0.7	39
0.7-0.8	3
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
0.7444	Intermediate Similarity	NPD7977	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD8339	Clinical (unspecified phase)
0.7092	Intermediate Similarity	NPD8071	Approved
0.7021	Intermediate Similarity	NPD6348	Clinical (unspecified phase)
0.6897	Remote Similarity	NPD5189	Clinical (unspecified phase)
0.6884	Remote Similarity	NPD8260	Approved
0.6878	Remote Similarity	NPD6349	Phase 1
0.6818	Remote Similarity	NPD5634	Approved
0.6737	Remote Similarity	NPD6632	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD3127	Clinical (unspecified phase)
0.6573	Remote Similarity	NPD6915	Approved
0.6569	Remote Similarity	NPD4742	Phase 3
0.6569	Remote Similarity	NPD4741	Phase 3
0.6558	Remote Similarity	NPD7806	Phase 2
0.649	Remote Similarity	NPD5191	Clinical (unspecified phase)
0.6481	Remote Similarity	NPD5702	Clinical (unspecified phase)
0.6455	Remote Similarity	NPD2957	Phase 2
0.6441	Remote Similarity	NPD3575	Approved
0.6441	Remote Similarity	NPD3576	Approved
0.6409	Remote Similarity	NPD4669	Clinical (unspecified phase)
0.6409	Remote Similarity	NPD4671	Clinical (unspecified phase)
0.6409	Remote Similarity	NPD4670	Clinical (unspecified phase)
0.6378	Remote Similarity	NPD4949	Discontinued
0.6359	Remote Similarity	NPD2015	Discontinued
0.6354	Remote Similarity	NPD5596	Phase 2
0.6275	Remote Similarity	NPD6888	Discontinued
0.6238	Remote Similarity	NPD5828	Phase 2
0.6215	Remote Similarity	NPD5595	Clinical (unspecified phase)
0.6205	Remote Similarity	NPD6092	Discontinued
0.6203	Remote Similarity	NPD7133	Discontinued
0.6188	Remote Similarity	NPD3469	Phase 3
0.6179	Remote Similarity	NPD7496	Phase 2
0.617	Remote Similarity	NPD6916	Clinical (unspecified phase)
0.6147	Remote Similarity	NPD7540	Clinical (unspecified phase)
0.6133	Remote Similarity	NPD6907	Phase 2
0.6126	Remote Similarity	NPD1260	Approved
0.6111	Remote Similarity	NPD1005	Phase 2
0.6111	Remote Similarity	NPD1004	Phase 2
0.6111	Remote Similarity	NPD6360	Discontinued
0.6105	Remote Similarity	NPD647	Approved
0.6103	Remote Similarity	NPD1745	Approved
0.6096	Remote Similarity	NPD5138	Approved
0.6096	Remote Similarity	NPD5140	Approved
0.6053	Remote Similarity	NPD4650	Approved
0.6049	Remote Similarity	NPD3907	Clinical (unspecified phase)
0.6047	Remote Similarity	NPD3759	Clinical (unspecified phase)
0.6045	Remote Similarity	NPD4856	Approved
0.6045	Remote Similarity	NPD4855	Phase 1
0.604	Remote Similarity	NPD3395	Approved
0.604	Remote Similarity	NPD3396	Approved
0.6039	Remote Similarity	NPD6324	Phase 1
0.6035	Remote Similarity	NPD7816	Clinical (unspecified phase)
0.6034	Remote Similarity	NPD649	Clinical (unspecified phase)
0.6022	Remote Similarity	NPD4557	Approved
0.6011	Remote Similarity	NPD5663	Discontinued
0.6011	Remote Similarity	NPD7836	Clinical (unspecified phase)
0.6011	Remote Similarity	NPD3834	Clinical (unspecified phase)
0.601	Remote Similarity	NPD6347	Phase 2
0.6	Remote Similarity	NPD6910	Phase 3
0.599	Remote Similarity	NPD4134	Clinical (unspecified phase)
0.599	Remote Similarity	NPD6751	Clinical (unspecified phase)
0.599	Remote Similarity	NPD6308	Phase 1
0.599	Remote Similarity	NPD7321	Clinical (unspecified phase)
0.5989	Remote Similarity	NPD7494	Clinical (unspecified phase)
0.598	Remote Similarity	NPD1219	Approved
0.598	Remote Similarity	NPD1218	Approved
0.598	Remote Similarity	NPD2749	Discontinued
0.5978	Remote Similarity	NPD3525	Discontinued
0.5977	Remote Similarity	NPD2202	Clinical (unspecified phase)
0.5974	Remote Similarity	NPD3328	Phase 2
0.5962	Remote Similarity	NPD7195	Clinical (unspecified phase)
0.5962	Remote Similarity	NPD5452	Phase 2
0.5959	Remote Similarity	NPD924	Discontinued
0.595	Remote Similarity	NPD8110	Clinical (unspecified phase)
0.5944	Remote Similarity	NPD3401	Clinical (unspecified phase)
0.5944	Remote Similarity	NPD5502	Approved
0.5944	Remote Similarity	NPD5503	Approved
0.5938	Remote Similarity	NPD754	Clinical (unspecified phase)
0.5938	Remote Similarity	NPD4929	Approved
0.5938	Remote Similarity	NPD4928	Approved
0.5938	Remote Similarity	NPD4930	Approved
0.5935	Remote Similarity	NPD4331	Approved
0.5933	Remote Similarity	NPD8272	Phase 2
0.5928	Remote Similarity	NPD2389	Approved
0.5926	Remote Similarity	NPD2543	Discontinued
0.5922	Remote Similarity	NPD1592	Phase 3
0.592	Remote Similarity	NPD5323	Approved
0.5918	Remote Similarity	NPD7104	Clinical (unspecified phase)
0.5914	Remote Similarity	NPD6911	Discontinued
0.5913	Remote Similarity	NPD5023	Discontinued
0.5911	Remote Similarity	NPD2717	Phase 2
0.5905	Remote Similarity	NPD6205	Discontinued
0.5902	Remote Similarity	NPD7490	Discontinued
0.5902	Remote Similarity	NPD5638	Approved
0.5897	Remote Similarity	NPD5755	Clinical (unspecified phase)
0.5896	Remote Similarity	NPD5299	Approved
0.5893	Remote Similarity	NPD4273	Approved
0.5892	Remote Similarity	NPD8284	Discontinued
0.5888	Remote Similarity	NPD2852	Approved
0.5882	Remote Similarity	NPD2581	Approved
0.5882	Remote Similarity	NPD2582	Approved
0.5879	Remote Similarity	NPD5439	Approved
0.5879	Remote Similarity	NPD3988	Approved
0.5879	Remote Similarity	NPD3987	Approved
0.5879	Remote Similarity	NPD6227	Discontinued
0.5879	Remote Similarity	NPD5438	Approved
0.5873	Remote Similarity	NPD3487	Phase 1
0.5868	Remote Similarity	NPD9579	Approved
0.5866	Remote Similarity	NPD6119	Clinical (unspecified phase)
0.586	Remote Similarity	NPD1597	Phase 1
0.5856	Remote Similarity	NPD4509	Discontinued
0.5853	Remote Similarity	NPD1976	Approved
0.5851	Remote Similarity	NPD5255	Approved
0.5843	Remote Similarity	NPD4209	Clinical (unspecified phase)
0.5842	Remote Similarity	NPD8129	Discovery
0.5838	Remote Similarity	NPD4646	Approved
0.5838	Remote Similarity	NPD4648	Approved
0.5838	Remote Similarity	NPD4647	Approved
0.5829	Remote Similarity	NPD1274	Clinical (unspecified phase)
0.5829	Remote Similarity	NPD2306	Approved
0.5824	Remote Similarity	NPD5367	Discontinued
0.5816	Remote Similarity	NPD2144	Approved
0.5814	Remote Similarity	NPD767	Phase 1
0.5813	Remote Similarity	NPD954	Phase 1
0.581	Remote Similarity	NPD2022	Approved
0.58	Remote Similarity	NPD3082	Discontinued
0.5794	Remote Similarity	NPD5435	Phase 1
0.5792	Remote Similarity	NPD2152	Clinical (unspecified phase)
0.5792	Remote Similarity	NPD3335	Approved
0.5792	Remote Similarity	NPD3611	Phase 3
0.5789	Remote Similarity	NPD1881	Approved
0.5789	Remote Similarity	NPD3494	Approved
0.5789	Remote Similarity	NPD5259	Phase 3
0.5789	Remote Similarity	NPD3493	Approved
0.5789	Remote Similarity	NPD3492	Approved
0.5787	Remote Similarity	NPD3480	Approved
0.5785	Remote Similarity	NPD7711	Discontinued
0.5784	Remote Similarity	NPD6819	Phase 2
0.5783	Remote Similarity	NPD2893	Phase 3
0.578	Remote Similarity	NPD4125	Approved
0.578	Remote Similarity	NPD5453	Phase 2
0.5775	Remote Similarity	NPD2891	Approved
0.5775	Remote Similarity	NPD7981	Discontinued
0.5771	Remote Similarity	NPD3334	Approved
0.5769	Remote Similarity	NPD1315	Clinical (unspecified phase)
0.5767	Remote Similarity	NPD704	Clinical (unspecified phase)
0.5767	Remote Similarity	NPD3223	Clinical (unspecified phase)
0.5764	Remote Similarity	NPD8063	Discontinued
0.5763	Remote Similarity	NPD740	Clinical (unspecified phase)
0.5762	Remote Similarity	NPD3015	Discontinued
0.5762	Remote Similarity	NPD1897	Discontinued
0.5759	Remote Similarity	NPD6170	Phase 2
0.5755	Remote Similarity	NPD7001	Phase 3
0.5755	Remote Similarity	NPD7289	Clinical (unspecified phase)
0.5753	Remote Similarity	NPD2882	Phase 1
0.5747	Remote Similarity	NPD2048	Approved
0.5747	Remote Similarity	NPD2044	Approved
0.5747	Remote Similarity	NPD2047	Approved
0.5747	Remote Similarity	NPD2043	Approved
0.5747	Remote Similarity	NPD2046	Approved
0.5747	Remote Similarity	NPD2045	Approved
0.5747	Remote Similarity	NPD2051	Approved
0.5747	Remote Similarity	NPD21	Approved
0.5747	Remote Similarity	NPD2050	Clinical (unspecified phase)
0.5747	Remote Similarity	NPD2049	Clinical (unspecified phase)
0.5746	Remote Similarity	NPD3838	Phase 3
0.5744	Remote Similarity	NPD5461	Discontinued
0.5743	Remote Similarity	NPD2383	Phase 1
0.5742	Remote Similarity	NPD4599	Clinical (unspecified phase)
0.574	Remote Similarity	NPD4480	Approved
0.574	Remote Similarity	NPD6246	Approved
0.5738	Remote Similarity	NPD1979	Approved
0.5738	Remote Similarity	NPD5414	Phase 2
0.5737	Remote Similarity	NPD7737	Approved
0.5737	Remote Similarity	NPD7738	Approved
0.5736	Remote Similarity	NPD3449	Discontinued
0.5736	Remote Similarity	NPD8122	Approved
0.5736	Remote Similarity	NPD8123	Approved
0.5735	Remote Similarity	NPD5144	Discontinued
0.5735	Remote Similarity	NPD6139	Clinical (unspecified phase)
0.5735	Remote Similarity	NPD8072	Approved
0.573	Remote Similarity	NPD5229	Approved
0.573	Remote Similarity	NPD5230	Approved
0.5729	Remote Similarity	NPD3038	Discontinued
0.5728	Remote Similarity	NPD4415	Approved
0.5728	Remote Similarity	NPD7834	Approved
0.5726	Remote Similarity	NPD8061	Clinical (unspecified phase)
0.5726	Remote Similarity	NPD5817	Discontinued
0.5722	Remote Similarity	NPD2088	Approved
0.5722	Remote Similarity	NPD2087	Approved
0.5721	Remote Similarity	NPD1789	Approved
0.5721	Remote Similarity	NPD1788	Approved
0.5714	Remote Similarity	NPD6492	Phase 2
0.5714	Remote Similarity	NPD5298	Clinical (unspecified phase)
0.5708	Remote Similarity	NPD4906	Approved
0.5708	Remote Similarity	NPD4905	Approved
0.5708	Remote Similarity	NPD4903	Approved
0.5708	Remote Similarity	NPD5524	Approved
0.5708	Remote Similarity	NPD4898	Clinical (unspecified phase)
0.5708	Remote Similarity	NPD5523	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