NPASS Compound

Structure

NPC66490 OpenBabel07101718292D 34 34 0 0 1 0 0 0 0 0999 V2000 3.4641 -7.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -5.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.7942 -7.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9282 -7.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.7942 -8.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 -8.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -6.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 -7.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.0000 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -5.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.4641 -3.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.5981 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 -6.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.6603 -10.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.5263 -10.5000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 7.7942 -10.5000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 8.6603 -9.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 -7.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -2.5000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -4.5000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 6.9282 -9.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 -5.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -4.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 13 1 0 0 0 0 2 13 1 0 0 0 0 3 14 1 0 0 0 0 4 14 1 0 0 0 0 5 6 1 0 0 0 0 5 11 1 0 0 0 0 7 9 1 0 0 0 0 7 15 2 0 0 0 0 8 10 2 0 0 0 0 8 15 1 0 0 0 0 9 17 2 0 0 0 0 10 17 1 0 0 0 0 11 26 1 0 0 0 0 12 16 1 0 0 0 0 12 30 2 0 0 0 0 15 20 1 0 0 0 0 16 6 1 1 0 0 0 16 27 1 0 0 0 0 17 31 1 0 0 0 0 18 13 1 6 0 0 0 18 21 1 0 0 0 0 18 29 1 0 0 0 0 19 14 1 1 0 0 0 19 22 1 0 0 0 0 19 28 1 0 0 0 0 20 28 1 0 0 0 0 20 32 2 0 0 0 0 21 27 2 3 0 0 0 21 33 1 0 0 0 0 22 29 2 3 0 0 0 22 34 1 0 0 0 0 23 24 2 0 0 0 0 23 25 1 0 0 0 0 23 26 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	476.27
Volume:	486.648
LogP:	0.345
LogD:	-0.004
LogS:	-2.815
# Rotatable Bonds:	16
TPSA:	189.0
# H-Bond Aceptor:	11
# H-Bond Donor:	8
# Rings:	1
# Heavy Atoms:	11

MedChem Properties

QED Drug-Likeness Score:	0.1
Synthetic Accessibility Score:	3.466
Fsp3:	0.522
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-6.282
MDCK Permeability:	1.3770384612143971e-05
Pgp-inhibitor:	0.001
Pgp-substrate:	0.997
Human Intestinal Absorption (HIA):	0.015
20% Bioavailability (F20%):	0.016
30% Bioavailability (F30%):	0.005

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.239
Plasma Protein Binding (PPB):	32.863033294677734%
Volume Distribution (VD):	1.197
Pgp-substrate:	67.4716796875%

ADMET: Metabolism

CYP1A2-inhibitor:	0.004
CYP1A2-substrate:	0.04
CYP2C19-inhibitor:	0.03
CYP2C19-substrate:	0.047
CYP2C9-inhibitor:	0.035
CYP2C9-substrate:	0.027
CYP2D6-inhibitor:	0.009
CYP2D6-substrate:	0.132
CYP3A4-inhibitor:	0.049
CYP3A4-substrate:	0.178

ADMET: Excretion

Clearance (CL):	5.73
Half-life (T1/2):	0.414

ADMET: Toxicity

hERG Blockers:	0.181
Human Hepatotoxicity (H-HT):	0.496
Drug-inuced Liver Injury (DILI):	0.504
AMES Toxicity:	0.007
Rat Oral Acute Toxicity:	0.04
Maximum Recommended Daily Dose:	0.033
Skin Sensitization:	0.154
Carcinogencity:	0.023
Eye Corrosion:	0.003
Eye Irritation:	0.005
Respiratory Toxicity:	0.06

Download Data

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

Natural Product: NPC66490

Natural Product ID:	NPC66490
*Common Name:**	Tokaramide A
IUPAC Name:	N-[(2S)-1-[[(2S)-1-[[(2S)-5-(diaminomethylideneamino)-1-oxopentan-2-yl]amino]-3-methyl-1-oxobutan-2-yl]amino]-3-methyl-1-oxobutan-2-yl]-4-hydroxybenzamide
Synonyms:
Standard InCHIKey:	QIOXCWRQNDIISW-WDSOQIARSA-N
Standard InCHI:	InChI=1S/C23H36N6O5/c1-13(2)18(21(33)27-16(12-30)6-5-11-26-23(24)25)29-22(34)19(14(3)4)28-20(32)15-7-9-17(31)10-8-15/h7-10,12-14,16,18-19,31H,5-6,11H2,1-4H3,(H,27,33)(H,28,32)(H,29,34)(H4,24,25,26)/t16-,18-,19-/m0/s1
SMILES:	O=C[C@@H](N=C([C@H](C(C)C)N=C([C@H](C(C)C)NC(=O)c1ccc(cc1)O)O)O)CCCNC(=N)N
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL117479
PubChem CID:	10457697
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:0004830] Dipeptides

*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
NPO32700	theonella aff. mirabilis	Species	Theonellidae	Eukaryota	n.a.	n.a.	n.a.	PMID[10617079]

☑ 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	1
Others	9

Activity Type	# Activity
Individual Protein	10

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT214	Individual Protein	Cathepsin B	Homo sapiens	Inhibition	~	10.0	%	PMID[493223]
NPT214	Individual Protein	Cathepsin B	Homo sapiens	Inhibition	~	12.0	%	PMID[493223]
NPT214	Individual Protein	Cathepsin B	Homo sapiens	Inhibition	~	16.0	%	PMID[493223]
NPT214	Individual Protein	Cathepsin B	Homo sapiens	Inhibition	~	30.0	%	PMID[493223]
NPT214	Individual Protein	Cathepsin B	Homo sapiens	Inhibition	~	45.0	%	PMID[493223]
NPT214	Individual Protein	Cathepsin B	Homo sapiens	Inhibition	~	70.0	%	PMID[493223]
NPT214	Individual Protein	Cathepsin B	Homo sapiens	Inhibition	~	80.0	%	PMID[493223]
NPT214	Individual Protein	Cathepsin B	Homo sapiens	Inhibition	~	90.0	%	PMID[493223]
NPT214	Individual Protein	Cathepsin B	Homo sapiens	Inhibition	~	100.0	%	PMID[493223]
NPT214	Individual Protein	Cathepsin B	Homo sapiens	IC50	=	0.029	ug.mL-1	PMID[493223]

☑ 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 NPC66490 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	203
0.1-0.2	2040
0.2-0.3	10081
0.3-0.4	6999
0.4-0.5	16040
0.5-0.6	6481
0.6-0.7	724
0.7-0.8	119
0.8-0.85	9
0.85-0.9	0
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.8095	Intermediate Similarity	NPC129486
0.8095	Intermediate Similarity	NPC280022
0.8057	Intermediate Similarity	NPC235194
0.8047	Intermediate Similarity	NPC198254
0.8047	Intermediate Similarity	NPC274198
0.8013	Intermediate Similarity	NPC238412
0.7953	Intermediate Similarity	NPC475532
0.7941	Intermediate Similarity	NPC276506
0.7907	Intermediate Similarity	NPC165285
0.7898	Intermediate Similarity	NPC48202
0.7861	Intermediate Similarity	NPC196243
0.7818	Intermediate Similarity	NPC473580
0.7803	Intermediate Similarity	NPC17698
0.7784	Intermediate Similarity	NPC473404
0.7771	Intermediate Similarity	NPC119652
0.7771	Intermediate Similarity	NPC97526
0.7738	Intermediate Similarity	NPC469243
0.768	Intermediate Similarity	NPC240130
0.768	Intermediate Similarity	NPC61332
0.7633	Intermediate Similarity	NPC475544
0.7627	Intermediate Similarity	NPC153554
0.7602	Intermediate Similarity	NPC223207
0.7569	Intermediate Similarity	NPC94862
0.7562	Intermediate Similarity	NPC214988
0.7558	Intermediate Similarity	NPC471771
0.7558	Intermediate Similarity	NPC304074
0.7558	Intermediate Similarity	NPC290755
0.7554	Intermediate Similarity	NPC302715
0.7532	Intermediate Similarity	NPC267237
0.7527	Intermediate Similarity	NPC102959
0.75	Intermediate Similarity	NPC16188
0.75	Intermediate Similarity	NPC311658
0.7486	Intermediate Similarity	NPC60516
0.7469	Intermediate Similarity	NPC168861
0.743	Intermediate Similarity	NPC475409
0.743	Intermediate Similarity	NPC475564
0.743	Intermediate Similarity	NPC170302
0.7381	Intermediate Similarity	NPC262166
0.733	Intermediate Similarity	NPC46009
0.7318	Intermediate Similarity	NPC473546
0.7299	Intermediate Similarity	NPC63931
0.7283	Intermediate Similarity	NPC96275
0.7278	Intermediate Similarity	NPC202198
0.7278	Intermediate Similarity	NPC56685
0.7267	Intermediate Similarity	NPC314835
0.7247	Intermediate Similarity	NPC306804
0.7235	Intermediate Similarity	NPC39431
0.7234	Intermediate Similarity	NPC477638
0.7234	Intermediate Similarity	NPC477632
0.7225	Intermediate Similarity	NPC114806
0.7225	Intermediate Similarity	NPC477551
0.7219	Intermediate Similarity	NPC233702
0.7216	Intermediate Similarity	NPC328649
0.7211	Intermediate Similarity	NPC477550
0.7211	Intermediate Similarity	NPC477552
0.7204	Intermediate Similarity	NPC477636
0.7204	Intermediate Similarity	NPC51047
0.7196	Intermediate Similarity	NPC477639
0.7195	Intermediate Similarity	NPC476989
0.7193	Intermediate Similarity	NPC244509
0.7193	Intermediate Similarity	NPC476268
0.7188	Intermediate Similarity	NPC326966
0.7184	Intermediate Similarity	NPC241794
0.7178	Intermediate Similarity	NPC313694
0.7178	Intermediate Similarity	NPC242159
0.7176	Intermediate Similarity	NPC5194
0.7176	Intermediate Similarity	NPC261934
0.7168	Intermediate Similarity	NPC24617
0.716	Intermediate Similarity	NPC473491
0.7135	Intermediate Similarity	NPC475123
0.7135	Intermediate Similarity	NPC469443
0.7135	Intermediate Similarity	NPC475204
0.7128	Intermediate Similarity	NPC477631
0.7126	Intermediate Similarity	NPC81026
0.7119	Intermediate Similarity	NPC209463
0.7118	Intermediate Similarity	NPC300443
0.711	Intermediate Similarity	NPC326349
0.711	Intermediate Similarity	NPC323336
0.7108	Intermediate Similarity	NPC326241
0.7088	Intermediate Similarity	NPC269750
0.7088	Intermediate Similarity	NPC194671
0.7078	Intermediate Similarity	NPC283760
0.7069	Intermediate Similarity	NPC244336
0.7066	Intermediate Similarity	NPC266741
0.7063	Intermediate Similarity	NPC325651
0.7062	Intermediate Similarity	NPC61004
0.7059	Intermediate Similarity	NPC246591
0.7059	Intermediate Similarity	NPC324081
0.7056	Intermediate Similarity	NPC137627
0.7056	Intermediate Similarity	NPC273755
0.7039	Intermediate Similarity	NPC160179
0.7022	Intermediate Similarity	NPC107938
0.7022	Intermediate Similarity	NPC294516
0.7017	Intermediate Similarity	NPC155506
0.7017	Intermediate Similarity	NPC279871
0.7017	Intermediate Similarity	NPC159767
0.7	Intermediate Similarity	NPC89831
0.6984	Remote Similarity	NPC470728
0.6978	Remote Similarity	NPC50016
0.6971	Remote Similarity	NPC319320
0.6971	Remote Similarity	NPC287757
0.6944	Remote Similarity	NPC40234
0.6943	Remote Similarity	NPC27581
0.6931	Remote Similarity	NPC283207
0.6927	Remote Similarity	NPC141957
0.6927	Remote Similarity	NPC329295
0.6927	Remote Similarity	NPC302597
0.6923	Remote Similarity	NPC476227
0.6923	Remote Similarity	NPC26108
0.6919	Remote Similarity	NPC220060
0.691	Remote Similarity	NPC189116
0.6906	Remote Similarity	NPC230611
0.6906	Remote Similarity	NPC328494
0.6902	Remote Similarity	NPC45037
0.6894	Remote Similarity	NPC296712
0.6884	Remote Similarity	NPC469444
0.6882	Remote Similarity	NPC119569
0.6875	Remote Similarity	NPC80514
0.6854	Remote Similarity	NPC191863
0.6854	Remote Similarity	NPC133470
0.6854	Remote Similarity	NPC289776
0.6852	Remote Similarity	NPC478147
0.6845	Remote Similarity	NPC91953
0.6832	Remote Similarity	NPC305717
0.6831	Remote Similarity	NPC473402
0.6831	Remote Similarity	NPC136797
0.6831	Remote Similarity	NPC473354
0.6831	Remote Similarity	NPC471165
0.6829	Remote Similarity	NPC328070
0.6826	Remote Similarity	NPC471201
0.6826	Remote Similarity	NPC322526
0.6824	Remote Similarity	NPC473804
0.6824	Remote Similarity	NPC314114
0.6818	Remote Similarity	NPC317254
0.6807	Remote Similarity	NPC6570
0.6796	Remote Similarity	NPC315388
0.679	Remote Similarity	NPC311753
0.6788	Remote Similarity	NPC266425
0.6786	Remote Similarity	NPC197921
0.6786	Remote Similarity	NPC473450
0.6782	Remote Similarity	NPC469445
0.678	Remote Similarity	NPC1390
0.678	Remote Similarity	NPC62104
0.6768	Remote Similarity	NPC257390
0.6766	Remote Similarity	NPC473055
0.6766	Remote Similarity	NPC473052
0.6755	Remote Similarity	NPC294951
0.6752	Remote Similarity	NPC319950
0.675	Remote Similarity	NPC194699
0.675	Remote Similarity	NPC219350
0.6747	Remote Similarity	NPC473360
0.6746	Remote Similarity	NPC469360
0.6738	Remote Similarity	NPC477637
0.673	Remote Similarity	NPC474862
0.6727	Remote Similarity	NPC244866
0.672	Remote Similarity	NPC299806
0.672	Remote Similarity	NPC315542
0.6707	Remote Similarity	NPC120251
0.6706	Remote Similarity	NPC13696
0.6705	Remote Similarity	NPC256689
0.6705	Remote Similarity	NPC123011
0.6685	Remote Similarity	NPC248670
0.6683	Remote Similarity	NPC478007
0.6667	Remote Similarity	NPC132636
0.6667	Remote Similarity	NPC471048
0.6667	Remote Similarity	NPC471050
0.6667	Remote Similarity	NPC471049
0.6649	Remote Similarity	NPC248862
0.6649	Remote Similarity	NPC476321
0.6649	Remote Similarity	NPC314083
0.6648	Remote Similarity	NPC473502
0.6634	Remote Similarity	NPC478005
0.6632	Remote Similarity	NPC138083
0.6631	Remote Similarity	NPC182057
0.6631	Remote Similarity	NPC147298
0.6631	Remote Similarity	NPC131450
0.663	Remote Similarity	NPC217804
0.663	Remote Similarity	NPC472923
0.663	Remote Similarity	NPC210377
0.663	Remote Similarity	NPC22883
0.663	Remote Similarity	NPC5719
0.6627	Remote Similarity	NPC208757
0.6625	Remote Similarity	NPC268348
0.6619	Remote Similarity	NPC478008
0.6618	Remote Similarity	NPC277306
0.6618	Remote Similarity	NPC469442
0.6614	Remote Similarity	NPC471526
0.6609	Remote Similarity	NPC476444
0.6609	Remote Similarity	NPC2672
0.6596	Remote Similarity	NPC39822
0.6593	Remote Similarity	NPC15068
0.6593	Remote Similarity	NPC254700
0.6584	Remote Similarity	NPC472538
0.658	Remote Similarity	NPC473305
0.658	Remote Similarity	NPC163961
0.6578	Remote Similarity	NPC14849
0.6576	Remote Similarity	NPC196091
0.6568	Remote Similarity	NPC236795
0.6567	Remote Similarity	NPC81845
0.6564	Remote Similarity	NPC477937

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 NPC66490 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	142
0.1-0.2	460
0.2-0.3	912
0.3-0.4	1506
0.4-0.5	3531
0.5-0.6	2271
0.6-0.7	306
0.7-0.8	21
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8221	Intermediate Similarity	NPD7495	Discontinued
0.7976	Intermediate Similarity	NPD8303	Discontinued
0.7914	Intermediate Similarity	NPD7523	Phase 3
0.7684	Intermediate Similarity	NPD5192	Clinical (unspecified phase)
0.7679	Intermediate Similarity	NPD8019	Approved
0.7546	Intermediate Similarity	NPD7066	Clinical (unspecified phase)
0.7516	Intermediate Similarity	NPD3632	Clinical (unspecified phase)
0.7515	Intermediate Similarity	NPD7118	Clinical (unspecified phase)
0.7469	Intermediate Similarity	NPD6809	Clinical (unspecified phase)
0.7438	Intermediate Similarity	NPD4782	Clinical (unspecified phase)
0.7391	Intermediate Similarity	NPD7617	Discontinued
0.7363	Intermediate Similarity	NPD5946	Clinical (unspecified phase)
0.7337	Intermediate Similarity	NPD6670	Clinical (unspecified phase)
0.7321	Intermediate Similarity	NPD6078	Clinical (unspecified phase)
0.7297	Intermediate Similarity	NPD6377	Clinical (unspecified phase)
0.7292	Intermediate Similarity	NPD5152	Clinical (unspecified phase)
0.7241	Intermediate Similarity	NPD4565	Clinical (unspecified phase)
0.7241	Intermediate Similarity	NPD4564	Clinical (unspecified phase)
0.7233	Intermediate Similarity	NPD3136	Phase 2
0.7195	Intermediate Similarity	NPD7450	Phase 2
0.7178	Intermediate Similarity	NPD4214	Discontinued
0.716	Intermediate Similarity	NPD5348	Clinical (unspecified phase)
0.7151	Intermediate Similarity	NPD3451	Clinical (unspecified phase)
0.7134	Intermediate Similarity	NPD4158	Clinical (unspecified phase)
0.7101	Intermediate Similarity	NPD6631	Clinical (unspecified phase)
0.7099	Intermediate Similarity	NPD4791	Clinical (unspecified phase)
0.7076	Intermediate Similarity	NPD1670	Discontinued
0.7073	Intermediate Similarity	NPD6901	Phase 3
0.7052	Intermediate Similarity	NPD7267	Clinical (unspecified phase)
0.7049	Intermediate Similarity	NPD5445	Approved
0.7037	Intermediate Similarity	NPD5729	Clinical (unspecified phase)
0.7018	Intermediate Similarity	NPD2186	Approved
0.7017	Intermediate Similarity	NPD5200	Clinical (unspecified phase)
0.6946	Remote Similarity	NPD8076	Discontinued
0.6941	Remote Similarity	NPD6884	Clinical (unspecified phase)
0.6927	Remote Similarity	NPD3659	Discontinued
0.6919	Remote Similarity	NPD7303	Discontinued
0.6907	Remote Similarity	NPD7810	Phase 3
0.6907	Remote Similarity	NPD7811	Phase 3
0.6897	Remote Similarity	NPD824	Approved
0.6875	Remote Similarity	NPD4517	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD7011	Discontinued
0.6867	Remote Similarity	NPD743	Approved
0.6857	Remote Similarity	NPD2592	Discontinued
0.6851	Remote Similarity	NPD4652	Approved
0.6845	Remote Similarity	NPD7978	Discontinued
0.6825	Remote Similarity	NPD3863	Clinical (unspecified phase)
0.6823	Remote Similarity	NPD6181	Discontinued
0.6821	Remote Similarity	NPD4186	Clinical (unspecified phase)
0.6816	Remote Similarity	NPD2098	Approved
0.6807	Remote Similarity	NPD6817	Clinical (unspecified phase)
0.6805	Remote Similarity	NPD5341	Clinical (unspecified phase)
0.6796	Remote Similarity	NPD2889	Approved
0.6796	Remote Similarity	NPD2888	Approved
0.6796	Remote Similarity	NPD2017	Approved
0.6796	Remote Similarity	NPD7485	Phase 3
0.6796	Remote Similarity	NPD2890	Approved
0.6796	Remote Similarity	NPD7484	Phase 3
0.6782	Remote Similarity	NPD7131	Phase 3
0.6769	Remote Similarity	NPD5856	Discontinued
0.6765	Remote Similarity	NPD2458	Approved
0.6765	Remote Similarity	NPD2459	Approved
0.6765	Remote Similarity	NPD2460	Phase 3
0.6753	Remote Similarity	NPD3964	Approved
0.6744	Remote Similarity	NPD8290	Clinical (unspecified phase)
0.6726	Remote Similarity	NPD6867	Clinical (unspecified phase)
0.6726	Remote Similarity	NPD6866	Clinical (unspecified phase)
0.6719	Remote Similarity	NPD5042	Phase 1
0.6707	Remote Similarity	NPD6919	Clinical (unspecified phase)
0.6706	Remote Similarity	NPD6681	Discovery
0.6705	Remote Similarity	NPD6682	Clinical (unspecified phase)
0.6704	Remote Similarity	NPD2097	Approved
0.6703	Remote Similarity	NPD3286	Discontinued
0.6702	Remote Similarity	NPD6608	Clinical (unspecified phase)
0.6701	Remote Similarity	NPD4413	Clinical (unspecified phase)
0.6685	Remote Similarity	NPD3589	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD5186	Approved
0.6667	Remote Similarity	NPD5183	Approved
0.6649	Remote Similarity	NPD6613	Clinical (unspecified phase)
0.6646	Remote Similarity	NPD7979	Clinical (unspecified phase)
0.6632	Remote Similarity	NPD5525	Clinical (unspecified phase)
0.6631	Remote Similarity	NPD3997	Approved
0.6631	Remote Similarity	NPD3998	Approved
0.6631	Remote Similarity	NPD3999	Approved
0.663	Remote Similarity	NPD1307	Phase 2
0.663	Remote Similarity	NPD1309	Phase 2
0.6629	Remote Similarity	NPD2541	Clinical (unspecified phase)
0.6626	Remote Similarity	NPD7451	Discontinued
0.6626	Remote Similarity	NPD5339	Clinical (unspecified phase)
0.6614	Remote Similarity	NPD7132	Clinical (unspecified phase)
0.6611	Remote Similarity	NPD5967	Approved
0.6611	Remote Similarity	NPD7318	Phase 3
0.6584	Remote Similarity	NPD2561	Approved
0.6584	Remote Similarity	NPD2562	Approved
0.6578	Remote Similarity	NPD3995	Approved
0.6578	Remote Similarity	NPD4092	Approved
0.6578	Remote Similarity	NPD3996	Approved
0.6578	Remote Similarity	NPD3993	Approved
0.6578	Remote Similarity	NPD3991	Approved
0.6578	Remote Similarity	NPD3994	Approved
0.6578	Remote Similarity	NPD3992	Approved
0.6576	Remote Similarity	NPD7608	Discontinued
0.6562	Remote Similarity	NPD6089	Clinical (unspecified phase)
0.6561	Remote Similarity	NPD9568	Approved
0.6561	Remote Similarity	NPD4087	Phase 2
0.6559	Remote Similarity	NPD3522	Approved
0.6552	Remote Similarity	NPD3519	Discontinued
0.655	Remote Similarity	NPD8162	Phase 2
0.655	Remote Similarity	NPD6795	Clinical (unspecified phase)
0.655	Remote Similarity	NPD8163	Clinical (unspecified phase)
0.6548	Remote Similarity	NPD7282	Approved
0.6545	Remote Similarity	NPD6851	Approved
0.6545	Remote Similarity	NPD6853	Approved
0.6541	Remote Similarity	NPD5137	Approved
0.6524	Remote Similarity	NPD4091	Approved
0.6519	Remote Similarity	NPD856	Approved
0.6519	Remote Similarity	NPD16	Approved
0.6519	Remote Similarity	NPD317	Approved
0.6519	Remote Similarity	NPD318	Approved
0.6517	Remote Similarity	NPD3455	Phase 2
0.6513	Remote Similarity	NPD5165	Clinical (unspecified phase)
0.6513	Remote Similarity	NPD5968	Phase 3
0.651	Remote Similarity	NPD3153	Approved
0.651	Remote Similarity	NPD3154	Approved
0.651	Remote Similarity	NPD6967	Phase 2
0.6508	Remote Similarity	NPD3518	Clinical (unspecified phase)
0.6508	Remote Similarity	NPD6297	Approved
0.6505	Remote Similarity	NPD6894	Phase 1
0.6502	Remote Similarity	NPD6973	Clinical (unspecified phase)
0.65	Remote Similarity	NPD7317	Phase 3
0.6494	Remote Similarity	NPD7602	Clinical (unspecified phase)
0.6489	Remote Similarity	NPD6020	Phase 2
0.6489	Remote Similarity	NPD3965	Phase 1
0.6477	Remote Similarity	NPD5556	Clinical (unspecified phase)
0.6477	Remote Similarity	NPD2874	Phase 2
0.6471	Remote Similarity	NPD3553	Approved
0.6471	Remote Similarity	NPD3552	Approved
0.6471	Remote Similarity	NPD4077	Clinical (unspecified phase)
0.6471	Remote Similarity	NPD6720	Clinical (unspecified phase)
0.6471	Remote Similarity	NPD3555	Approved
0.6471	Remote Similarity	NPD3554	Approved
0.6468	Remote Similarity	NPD7316	Discontinued
0.6462	Remote Similarity	NPD5077	Approved
0.6462	Remote Similarity	NPD5076	Approved
0.6461	Remote Similarity	NPD5267	Discontinued
0.6458	Remote Similarity	NPD6618	Phase 2
0.6458	Remote Similarity	NPD6557	Phase 2
0.6453	Remote Similarity	NPD7607	Clinical (unspecified phase)
0.645	Remote Similarity	NPD3908	Approved
0.6443	Remote Similarity	NPD8025	Phase 2
0.6441	Remote Similarity	NPD7613	Discontinued
0.6436	Remote Similarity	NPD6480	Clinical (unspecified phase)
0.6436	Remote Similarity	NPD2361	Approved
0.6433	Remote Similarity	NPD5301	Clinical (unspecified phase)
0.6433	Remote Similarity	NPD7728	Clinical (unspecified phase)
0.6425	Remote Similarity	NPD3229	Phase 2
0.642	Remote Similarity	NPD8165	Discontinued
0.642	Remote Similarity	NPD6088	Approved
0.6416	Remote Similarity	NPD3655	Clinical (unspecified phase)
0.6412	Remote Similarity	NPD2568	Approved
0.6412	Remote Similarity	NPD3528	Clinical (unspecified phase)
0.641	Remote Similarity	NPD4258	Approved
0.641	Remote Similarity	NPD4259	Approved
0.6406	Remote Similarity	NPD1639	Discontinued
0.6402	Remote Similarity	NPD3125	Approved
0.6396	Remote Similarity	NPD4466	Phase 1
0.6395	Remote Similarity	NPD3175	Clinical (unspecified phase)
0.6392	Remote Similarity	NPD2942	Phase 2
0.6389	Remote Similarity	NPD1337	Clinical (unspecified phase)
0.6387	Remote Similarity	NPD3990	Phase 3
0.6387	Remote Similarity	NPD5637	Discontinued
0.6386	Remote Similarity	NPD4971	Clinical (unspecified phase)
0.6383	Remote Similarity	NPD2359	Approved
0.6383	Remote Similarity	NPD3366	Approved
0.638	Remote Similarity	NPD2584	Suspended
0.6379	Remote Similarity	NPD6860	Clinical (unspecified phase)
0.6379	Remote Similarity	NPD2976	Clinical (unspecified phase)
0.6378	Remote Similarity	NPD5823	Approved
0.6375	Remote Similarity	NPD316	Approved
0.6369	Remote Similarity	NPD598	Approved
0.6369	Remote Similarity	NPD1329	Clinical (unspecified phase)
0.6369	Remote Similarity	NPD601	Approved
0.6369	Remote Similarity	NPD597	Approved
0.6369	Remote Similarity	NPD1330	Phase 2
0.6368	Remote Similarity	NPD7695	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD3606	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD160	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD7669	Phase 3
0.6359	Remote Similarity	NPD7291	Discontinued
0.6359	Remote Similarity	NPD4157	Discontinued
0.6358	Remote Similarity	NPD2688	Clinical (unspecified phase)
0.6355	Remote Similarity	NPD3802	Phase 3
0.6353	Remote Similarity	NPD4757	Clinical (unspecified phase)
0.6353	Remote Similarity	NPD555	Phase 2
0.6349	Remote Similarity	NPD2822	Clinical (unspecified phase)
0.6349	Remote Similarity	NPD5940	Clinical (unspecified phase)
0.6343	Remote Similarity	NPD5481	Discontinued
0.6343	Remote Similarity	NPD1967	Approved
0.6343	Remote Similarity	NPD1968	Approved
0.6335	Remote Similarity	NPD3989	Phase 3

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