NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	280.11
Volume:	274.974
LogP:	0.757
LogD:	0.832
LogS:	-2.535
# Rotatable Bonds:	8
TPSA:	104.73
# H-Bond Aceptor:	7
# H-Bond Donor:	3
# Rings:	1
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.758
Synthetic Accessibility Score:	2.368
Fsp3:	0.308
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.728
MDCK Permeability:	2.9252414606162347e-05
Pgp-inhibitor:	0.0
Pgp-substrate:	0.734
Human Intestinal Absorption (HIA):	0.037
20% Bioavailability (F20%):	0.003
30% Bioavailability (F30%):	0.182

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.874
Plasma Protein Binding (PPB):	33.550086975097656%
Volume Distribution (VD):	0.232
Pgp-substrate:	64.46192932128906%

ADMET: Metabolism

CYP1A2-inhibitor:	0.014
CYP1A2-substrate:	0.099
CYP2C19-inhibitor:	0.057
CYP2C19-substrate:	0.079
CYP2C9-inhibitor:	0.011
CYP2C9-substrate:	0.802
CYP2D6-inhibitor:	0.008
CYP2D6-substrate:	0.157
CYP3A4-inhibitor:	0.011
CYP3A4-substrate:	0.086

ADMET: Excretion

Clearance (CL):	1.374
Half-life (T1/2):	0.875

ADMET: Toxicity

hERG Blockers:	0.014
Human Hepatotoxicity (H-HT):	0.168
Drug-inuced Liver Injury (DILI):	0.954
AMES Toxicity:	0.021
Rat Oral Acute Toxicity:	0.008
Maximum Recommended Daily Dose:	0.006
Skin Sensitization:	0.09
Carcinogencity:	0.05
Eye Corrosion:	0.003
Eye Irritation:	0.03
Respiratory Toxicity:	0.013

Download Data

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

Natural Product: NPC287358

Natural Product ID:	NPC287358
*Common Name:**	Giganticine
IUPAC Name:	(2S)-2-acetamido-2-[4-(ethoxycarbonylamino)phenyl]acetic acid
Synonyms:	Giganticine
Standard InCHIKey:	LXZCEJOKBHKJLM-NSHDSACASA-N
Standard InCHI:	InChI=1S/C13H16N2O5/c1-3-20-13(19)15-10-6-4-9(5-7-10)11(12(17)18)14-8(2)16/h4-7,11H,3H2,1-2H3,(H,14,16)(H,15,19)(H,17,18)/t11-/m0/s1
SMILES:	CCOC(=O)Nc1ccc(cc1)[C@@H](C(=O)O)N=C(O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL477129
PubChem CID:	10850332
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:0000347] Amino acids and derivatives [CHEMONTID:0000060] Alpha amino acids and derivatives [CHEMONTID:0001189] N-acyl-alpha amino acids and derivatives [CHEMONTID:0002402] N-acyl-alpha amino acids [CHEMONTID:0004148] N-acyl-L-alpha-amino acids

*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
NPO30295	Calotropis gigantea	Species	Apocynaceae	Eukaryota	leaves	n.a.	n.a.	PMID[16933890]
NPO30295	Calotropis gigantea	Species	Apocynaceae	Eukaryota	n.a.	root	n.a.	PMID[19052526]
NPO30295	Calotropis gigantea	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[28817274]
NPO30295	Calotropis gigantea	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[31967821]
NPO30295	Calotropis gigantea	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[32649211]
NPO30295	Calotropis gigantea	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[9548837]

☑ 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
Others	4

Activity Type	# Activity
Organism	4

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT3772	Organism	Schistocerca gregaria	Schistocerca gregaria	Activity	=	80.0	%	PMID[494326]
NPT3772	Organism	Schistocerca gregaria	Schistocerca gregaria	Activity	=	90.0	%	PMID[494326]
NPT3772	Organism	Schistocerca gregaria	Schistocerca gregaria	Activity	=	68.0	%	PMID[494326]
NPT3772	Organism	Schistocerca gregaria	Schistocerca gregaria	Activity	=	55.0	%	PMID[494326]

☑ 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 NPC287358 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	140
0.1-0.2	1370
0.2-0.3	8020
0.3-0.4	17440
0.4-0.5	11148
0.5-0.6	3758
0.6-0.7	780
0.7-0.8	40
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.7568	Intermediate Similarity	NPC472241
0.7533	Intermediate Similarity	NPC472242
0.75	Intermediate Similarity	NPC474926
0.7483	Intermediate Similarity	NPC478039
0.7432	Intermediate Similarity	NPC472243
0.7407	Intermediate Similarity	NPC197470
0.7383	Intermediate Similarity	NPC43477
0.7351	Intermediate Similarity	NPC314186
0.7329	Intermediate Similarity	NPC253476
0.7324	Intermediate Similarity	NPC322433
0.7315	Intermediate Similarity	NPC242933
0.7313	Intermediate Similarity	NPC474584
0.7287	Intermediate Similarity	NPC164859
0.7254	Intermediate Similarity	NPC205946
0.7252	Intermediate Similarity	NPC327481
0.7241	Intermediate Similarity	NPC314098
0.7239	Intermediate Similarity	NPC329011
0.7205	Intermediate Similarity	NPC189116
0.7188	Intermediate Similarity	NPC12730
0.7179	Intermediate Similarity	NPC314223
0.7172	Intermediate Similarity	NPC314431
0.7164	Intermediate Similarity	NPC319579
0.7162	Intermediate Similarity	NPC173295
0.7153	Intermediate Similarity	NPC58827
0.7153	Intermediate Similarity	NPC307437
0.7153	Intermediate Similarity	NPC72473
0.7143	Intermediate Similarity	NPC259678
0.7133	Intermediate Similarity	NPC319645
0.7055	Intermediate Similarity	NPC472245
0.705	Intermediate Similarity	NPC169328
0.7045	Intermediate Similarity	NPC476198
0.7045	Intermediate Similarity	NPC67043
0.7039	Intermediate Similarity	NPC316202
0.7006	Intermediate Similarity	NPC248862
0.7	Intermediate Similarity	NPC314992
0.7	Intermediate Similarity	NPC310467
0.6993	Remote Similarity	NPC35996
0.6986	Remote Similarity	NPC150863
0.6978	Remote Similarity	NPC2265
0.6966	Remote Similarity	NPC477937
0.6948	Remote Similarity	NPC314287
0.6944	Remote Similarity	NPC317758
0.6923	Remote Similarity	NPC14849
0.6905	Remote Similarity	NPC328611
0.6901	Remote Similarity	NPC150323
0.6899	Remote Similarity	NPC122493
0.6899	Remote Similarity	NPC10781
0.6899	Remote Similarity	NPC293628
0.6897	Remote Similarity	NPC4974
0.6897	Remote Similarity	NPC470343
0.6897	Remote Similarity	NPC472244
0.6882	Remote Similarity	NPC182057
0.6882	Remote Similarity	NPC131450
0.6882	Remote Similarity	NPC147298
0.6867	Remote Similarity	NPC470971
0.6835	Remote Similarity	NPC300596
0.6835	Remote Similarity	NPC237649
0.6824	Remote Similarity	NPC280807
0.6821	Remote Similarity	NPC314835
0.6805	Remote Similarity	NPC13367
0.6797	Remote Similarity	NPC181527
0.6783	Remote Similarity	NPC80150
0.6783	Remote Similarity	NPC190663
0.6781	Remote Similarity	NPC47667
0.6772	Remote Similarity	NPC254798
0.6769	Remote Similarity	NPC324569
0.6768	Remote Similarity	NPC143457
0.6768	Remote Similarity	NPC68650
0.6768	Remote Similarity	NPC472102
0.6768	Remote Similarity	NPC309531
0.6763	Remote Similarity	NPC57051
0.6761	Remote Similarity	NPC229353
0.6761	Remote Similarity	NPC237420
0.6748	Remote Similarity	NPC153694
0.6748	Remote Similarity	NPC211525
0.6743	Remote Similarity	NPC282092
0.6733	Remote Similarity	NPC476689
0.6733	Remote Similarity	NPC476687
0.6733	Remote Similarity	NPC476685
0.6732	Remote Similarity	NPC132636
0.6727	Remote Similarity	NPC176983
0.6727	Remote Similarity	NPC286871
0.6712	Remote Similarity	NPC226794
0.6711	Remote Similarity	NPC194562
0.6707	Remote Similarity	NPC148468
0.6707	Remote Similarity	NPC243673
0.6707	Remote Similarity	NPC36495
0.6707	Remote Similarity	NPC63210
0.6707	Remote Similarity	NPC310403
0.6707	Remote Similarity	NPC263709
0.6707	Remote Similarity	NPC182131
0.6707	Remote Similarity	NPC97380
0.669	Remote Similarity	NPC160493
0.669	Remote Similarity	NPC27581
0.6688	Remote Similarity	NPC315224
0.6667	Remote Similarity	NPC474479
0.6667	Remote Similarity	NPC201424
0.6667	Remote Similarity	NPC267885
0.6667	Remote Similarity	NPC316405
0.6667	Remote Similarity	NPC130931
0.6667	Remote Similarity	NPC478016
0.6667	Remote Similarity	NPC478015
0.6667	Remote Similarity	NPC477159
0.6667	Remote Similarity	NPC478014
0.6648	Remote Similarity	NPC235684
0.6647	Remote Similarity	NPC285622
0.6646	Remote Similarity	NPC61013
0.6646	Remote Similarity	NPC123241
0.6645	Remote Similarity	NPC315051
0.6643	Remote Similarity	NPC35850
0.6643	Remote Similarity	NPC276949
0.6642	Remote Similarity	NPC471317
0.6629	Remote Similarity	NPC473298
0.6627	Remote Similarity	NPC253667
0.6627	Remote Similarity	NPC35510
0.6627	Remote Similarity	NPC472121
0.6624	Remote Similarity	NPC478040
0.6623	Remote Similarity	NPC246913
0.6623	Remote Similarity	NPC122553
0.6621	Remote Similarity	NPC71684
0.6608	Remote Similarity	NPC149155
0.6608	Remote Similarity	NPC203468
0.6608	Remote Similarity	NPC110500
0.6607	Remote Similarity	NPC472115
0.6607	Remote Similarity	NPC472114
0.6606	Remote Similarity	NPC193410
0.66	Remote Similarity	NPC187231
0.66	Remote Similarity	NPC325651
0.6597	Remote Similarity	NPC226143
0.6597	Remote Similarity	NPC319950
0.6596	Remote Similarity	NPC470550
0.6596	Remote Similarity	NPC33742
0.6596	Remote Similarity	NPC205652
0.6591	Remote Similarity	NPC322598
0.659	Remote Similarity	NPC126709
0.659	Remote Similarity	NPC248041
0.659	Remote Similarity	NPC283219
0.659	Remote Similarity	NPC219336
0.6577	Remote Similarity	NPC210950
0.6577	Remote Similarity	NPC199738
0.6573	Remote Similarity	NPC284706
0.6566	Remote Similarity	NPC248117
0.6564	Remote Similarity	NPC471132
0.6562	Remote Similarity	NPC315829
0.6554	Remote Similarity	NPC101719
0.6552	Remote Similarity	NPC279385
0.6552	Remote Similarity	NPC179605
0.6552	Remote Similarity	NPC469896
0.6548	Remote Similarity	NPC52059
0.6548	Remote Similarity	NPC470069
0.6545	Remote Similarity	NPC104345
0.6545	Remote Similarity	NPC24617
0.6536	Remote Similarity	NPC316104
0.6536	Remote Similarity	NPC162417
0.6534	Remote Similarity	NPC245741
0.6534	Remote Similarity	NPC471742
0.6534	Remote Similarity	NPC97584
0.6533	Remote Similarity	NPC311753
0.6533	Remote Similarity	NPC101372
0.6533	Remote Similarity	NPC122235
0.6533	Remote Similarity	NPC296712
0.6532	Remote Similarity	NPC15573
0.6532	Remote Similarity	NPC183662
0.6532	Remote Similarity	NPC217372
0.6531	Remote Similarity	NPC254698
0.6527	Remote Similarity	NPC99632
0.6527	Remote Similarity	NPC282339
0.6527	Remote Similarity	NPC472120
0.6527	Remote Similarity	NPC472101
0.6527	Remote Similarity	NPC293458
0.6524	Remote Similarity	NPC161827
0.6519	Remote Similarity	NPC474430
0.6519	Remote Similarity	NPC178681
0.6507	Remote Similarity	NPC103292
0.6506	Remote Similarity	NPC114806
0.6503	Remote Similarity	NPC90967
0.65	Remote Similarity	NPC146370
0.6497	Remote Similarity	NPC468984
0.6494	Remote Similarity	NPC475094
0.6494	Remote Similarity	NPC218594
0.6494	Remote Similarity	NPC99043
0.649	Remote Similarity	NPC477432
0.6488	Remote Similarity	NPC113056
0.6488	Remote Similarity	NPC292143
0.6488	Remote Similarity	NPC138293
0.6488	Remote Similarity	NPC139506
0.6486	Remote Similarity	NPC222466
0.6485	Remote Similarity	NPC63370
0.6485	Remote Similarity	NPC36836
0.6485	Remote Similarity	NPC29285
0.6481	Remote Similarity	NPC473329
0.6481	Remote Similarity	NPC300443
0.648	Remote Similarity	NPC175474
0.6478	Remote Similarity	NPC314114
0.6471	Remote Similarity	NPC470392
0.6467	Remote Similarity	NPC474058
0.6467	Remote Similarity	NPC225319
0.6467	Remote Similarity	NPC27904
0.6463	Remote Similarity	NPC469903
0.6463	Remote Similarity	NPC142577

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 NPC287358 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	110
0.1-0.2	395
0.2-0.3	926
0.3-0.4	1167
0.4-0.5	3363
0.5-0.6	2539
0.6-0.7	588
0.7-0.8	60
0.8-0.85	2
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8378	Intermediate Similarity	NPD7105	Phase 1
0.8125	Intermediate Similarity	NPD181	Approved
0.7987	Intermediate Similarity	NPD5982	Phase 2
0.7986	Intermediate Similarity	NPD1070	Approved
0.7986	Intermediate Similarity	NPD1069	Approved
0.777	Intermediate Similarity	NPD2887	Clinical (unspecified phase)
0.7733	Intermediate Similarity	NPD5942	Approved
0.7733	Intermediate Similarity	NPD5941	Approved
0.7703	Intermediate Similarity	NPD3016	Clinical (unspecified phase)
0.766	Intermediate Similarity	NPD6359	Clinical (unspecified phase)
0.7635	Intermediate Similarity	NPD5024	Approved
0.7517	Intermediate Similarity	NPD1071	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD1036	Approved
0.75	Intermediate Similarity	NPD3625	Discontinued
0.7482	Intermediate Similarity	NPD1360	Approved
0.7464	Intermediate Similarity	NPD1079	Discontinued
0.7448	Intermediate Similarity	NPD5185	Approved
0.7448	Intermediate Similarity	NPD5182	Approved
0.7448	Intermediate Similarity	NPD5184	Approved
0.7434	Intermediate Similarity	NPD1801	Approved
0.7434	Intermediate Similarity	NPD1802	Approved
0.7407	Intermediate Similarity	NPD1348	Approved
0.7386	Intermediate Similarity	NPD4432	Discontinued
0.7378	Intermediate Similarity	NPD8022	Clinical (unspecified phase)
0.7343	Intermediate Similarity	NPD1781	Discontinued
0.7342	Intermediate Similarity	NPD7599	Phase 2
0.7338	Intermediate Similarity	NPD5748	Phase 2
0.7324	Intermediate Similarity	NPD9540	Approved
0.7296	Intermediate Similarity	NPD7600	Phase 2
0.7285	Intermediate Similarity	NPD2820	Phase 3
0.7273	Intermediate Similarity	NPD1664	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD7528	Approved
0.7267	Intermediate Similarity	NPD5430	Discontinued
0.7241	Intermediate Similarity	NPD1619	Phase 3
0.7222	Intermediate Similarity	NPD766	Clinical (unspecified phase)
0.7219	Intermediate Similarity	NPD2365	Approved
0.7215	Intermediate Similarity	NPD1663	Discontinued
0.7212	Intermediate Similarity	NPD5466	Approved
0.7197	Intermediate Similarity	NPD2603	Clinical (unspecified phase)
0.7184	Intermediate Similarity	NPD7429	Clinical (unspecified phase)
0.7183	Intermediate Similarity	NPD9539	Approved
0.7183	Intermediate Similarity	NPD9541	Approved
0.7181	Intermediate Similarity	NPD4077	Clinical (unspecified phase)
0.7162	Intermediate Similarity	NPD1228	Phase 2
0.7161	Intermediate Similarity	NPD4161	Discontinued
0.7143	Intermediate Similarity	NPD5445	Approved
0.7133	Intermediate Similarity	NPD1110	Approved
0.7133	Intermediate Similarity	NPD3170	Approved
0.7133	Intermediate Similarity	NPD6864	Phase 2
0.7133	Intermediate Similarity	NPD6865	Phase 2
0.7133	Intermediate Similarity	NPD1109	Approved
0.7123	Intermediate Similarity	NPD4738	Phase 2
0.7108	Intermediate Similarity	NPD5919	Clinical (unspecified phase)
0.7107	Intermediate Similarity	NPD6913	Approved
0.7091	Intermediate Similarity	NPD4150	Clinical (unspecified phase)
0.7089	Intermediate Similarity	NPD5086	Approved
0.7086	Intermediate Similarity	NPD989	Approved
0.7078	Intermediate Similarity	NPD5060	Phase 1
0.7071	Intermediate Similarity	NPD4504	Clinical (unspecified phase)
0.7067	Intermediate Similarity	NPD2670	Approved
0.7063	Intermediate Similarity	NPD212	Discontinued
0.7051	Intermediate Similarity	NPD4888	Discontinued
0.7048	Intermediate Similarity	NPD7854	Phase 2
0.7047	Intermediate Similarity	NPD2470	Clinical (unspecified phase)
0.7045	Intermediate Similarity	NPD1040	Phase 2
0.7012	Intermediate Similarity	NPD3587	Clinical (unspecified phase)
0.7007	Intermediate Similarity	NPD1681	Approved
0.7007	Intermediate Similarity	NPD1680	Approved
0.7007	Intermediate Similarity	NPD1682	Approved
0.7	Intermediate Similarity	NPD2217	Approved
0.7	Intermediate Similarity	NPD2218	Phase 2
0.6993	Remote Similarity	NPD2584	Suspended
0.6987	Remote Similarity	NPD1553	Approved
0.6974	Remote Similarity	NPD1209	Approved
0.6974	Remote Similarity	NPD1205	Approved
0.6966	Remote Similarity	NPD553	Approved
0.6966	Remote Similarity	NPD9567	Approved
0.6966	Remote Similarity	NPD552	Approved
0.6964	Remote Similarity	NPD4091	Approved
0.6963	Remote Similarity	NPD1107	Approved
0.6963	Remote Similarity	NPD1108	Approved
0.6954	Remote Similarity	NPD3096	Phase 2
0.6954	Remote Similarity	NPD6294	Approved
0.6954	Remote Similarity	NPD6295	Approved
0.6948	Remote Similarity	NPD1625	Approved
0.6943	Remote Similarity	NPD4682	Phase 2
0.6941	Remote Similarity	NPD6833	Clinical (unspecified phase)
0.6939	Remote Similarity	NPD2919	Clinical (unspecified phase)
0.6939	Remote Similarity	NPD2918	Clinical (unspecified phase)
0.6928	Remote Similarity	NPD3434	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD3991	Approved
0.6923	Remote Similarity	NPD3992	Approved
0.6923	Remote Similarity	NPD3995	Approved
0.6923	Remote Similarity	NPD3996	Approved
0.6923	Remote Similarity	NPD3993	Approved
0.6923	Remote Similarity	NPD3994	Approved
0.6923	Remote Similarity	NPD4092	Approved
0.6918	Remote Similarity	NPD5993	Phase 1
0.6914	Remote Similarity	NPD4335	Clinical (unspecified phase)
0.6905	Remote Similarity	NPD3522	Approved
0.6901	Remote Similarity	NPD9272	Approved
0.6899	Remote Similarity	NPD9566	Approved
0.6897	Remote Similarity	NPD8103	Clinical (unspecified phase)
0.6882	Remote Similarity	NPD3997	Approved
0.6882	Remote Similarity	NPD3999	Approved
0.6882	Remote Similarity	NPD3998	Approved
0.6875	Remote Similarity	NPD5042	Phase 1
0.6859	Remote Similarity	NPD4711	Clinical (unspecified phase)
0.6853	Remote Similarity	NPD1124	Approved
0.6853	Remote Similarity	NPD1123	Approved
0.6846	Remote Similarity	NPD5581	Approved
0.6846	Remote Similarity	NPD864	Approved
0.6846	Remote Similarity	NPD865	Approved
0.6842	Remote Similarity	NPD4214	Discontinued
0.6832	Remote Similarity	NPD5257	Clinical (unspecified phase)
0.6828	Remote Similarity	NPD1640	Clinical (unspecified phase)
0.6818	Remote Similarity	NPD2093	Discontinued
0.6813	Remote Similarity	NPD1879	Approved
0.68	Remote Similarity	NPD1316	Discontinued
0.6797	Remote Similarity	NPD1626	Approved
0.6788	Remote Similarity	NPD3643	Approved
0.6788	Remote Similarity	NPD3642	Approved
0.6788	Remote Similarity	NPD3644	Approved
0.6788	Remote Similarity	NPD3790	Phase 2
0.6776	Remote Similarity	NPD1206	Approved
0.6776	Remote Similarity	NPD1207	Approved
0.6774	Remote Similarity	NPD1189	Approved
0.6772	Remote Similarity	NPD7441	Clinical (unspecified phase)
0.677	Remote Similarity	NPD1634	Approved
0.6765	Remote Similarity	NPD476	Approved
0.6763	Remote Similarity	NPD1373	Approved
0.6763	Remote Similarity	NPD1374	Approved
0.6763	Remote Similarity	NPD1371	Approved
0.6763	Remote Similarity	NPD23	Approved
0.6763	Remote Similarity	NPD1370	Approved
0.6761	Remote Similarity	NPD922	Approved
0.6759	Remote Similarity	NPD5108	Clinical (unspecified phase)
0.6757	Remote Similarity	NPD4177	Approved
0.6757	Remote Similarity	NPD4175	Approved
0.6753	Remote Similarity	NPD4707	Clinical (unspecified phase)
0.6748	Remote Similarity	NPD8630	Approved
0.6744	Remote Similarity	NPD3989	Phase 3
0.6742	Remote Similarity	NPD7570	Approved
0.6742	Remote Similarity	NPD7569	Approved
0.6738	Remote Similarity	NPD732	Approved
0.6738	Remote Similarity	NPD733	Approved
0.6738	Remote Similarity	NPD5162	Approved
0.6735	Remote Similarity	NPD6302	Clinical (unspecified phase)
0.6735	Remote Similarity	NPD3606	Clinical (unspecified phase)
0.6732	Remote Similarity	NPD6852	Discontinued
0.6731	Remote Similarity	NPD4464	Clinical (unspecified phase)
0.6726	Remote Similarity	NPD2369	Discontinued
0.6725	Remote Similarity	NPD7587	Clinical (unspecified phase)
0.6712	Remote Similarity	NPD4677	Discontinued
0.6711	Remote Similarity	NPD2331	Discontinued
0.6708	Remote Similarity	NPD1633	Approved
0.6707	Remote Similarity	NPD4514	Approved
0.6705	Remote Similarity	NPD3990	Phase 3
0.669	Remote Similarity	NPD4176	Approved
0.669	Remote Similarity	NPD4178	Approved
0.6689	Remote Similarity	NPD3137	Clinical (unspecified phase)
0.6688	Remote Similarity	NPD12	Approved
0.6688	Remote Similarity	NPD4158	Clinical (unspecified phase)
0.6688	Remote Similarity	NPD1967	Approved
0.6688	Remote Similarity	NPD1968	Approved
0.6688	Remote Similarity	NPD699	Approved
0.6688	Remote Similarity	NPD697	Approved
0.6688	Remote Similarity	NPD700	Approved
0.6688	Remote Similarity	NPD13	Approved
0.6687	Remote Similarity	NPD2836	Approved
0.6687	Remote Similarity	NPD2737	Clinical (unspecified phase)
0.6686	Remote Similarity	NPD6557	Phase 2
0.6686	Remote Similarity	NPD6163	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD2844	Phase 3
0.6667	Remote Similarity	NPD1324	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6768	Approved
0.6667	Remote Similarity	NPD564	Approved
0.6667	Remote Similarity	NPD3136	Phase 2
0.6667	Remote Similarity	NPD7794	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD2360	Approved
0.6667	Remote Similarity	NPD6489	Phase 3
0.6667	Remote Similarity	NPD563	Approved
0.6647	Remote Similarity	NPD750	Phase 2
0.6647	Remote Similarity	NPD7014	Clinical (unspecified phase)
0.6646	Remote Similarity	NPD5715	Clinical (unspecified phase)
0.6644	Remote Similarity	NPD519	Approved
0.6644	Remote Similarity	NPD3072	Approved
0.6644	Remote Similarity	NPD3071	Approved
0.6644	Remote Similarity	NPD3073	Approved
0.6627	Remote Similarity	NPD2350	Clinical (unspecified phase)
0.6625	Remote Similarity	NPD979	Approved
0.6624	Remote Similarity	NPD6301	Phase 2
0.6623	Remote Similarity	NPD5299	Approved
0.6621	Remote Similarity	NPD9692	Approved
0.6621	Remote Similarity	NPD9693	Approved
0.6608	Remote Similarity	NPD482	Approved
0.6597	Remote Similarity	NPD5981	Approved
0.6597	Remote Similarity	NPD2212	Approved
0.6597	Remote Similarity	NPD2210	Approved
0.6592	Remote Similarity	NPD5077	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