NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	180.04
Volume:	177.642
LogP:	1.552
LogD:	1.845
LogS:	-1.142
# Rotatable Bonds:	2
TPSA:	77.76
# H-Bond Aceptor:	4
# H-Bond Donor:	3
# Rings:	1
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.472
Synthetic Accessibility Score:	2.207
Fsp3:	0.0
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	1
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.111
MDCK Permeability:	1.0435876902192831e-05
Pgp-inhibitor:	0.0
Pgp-substrate:	0.015
Human Intestinal Absorption (HIA):	0.01
20% Bioavailability (F20%):	0.019
30% Bioavailability (F30%):	0.422

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.133
Plasma Protein Binding (PPB):	86.7691421508789%
Volume Distribution (VD):	0.36
Pgp-substrate:	14.088726043701172%

ADMET: Metabolism

CYP1A2-inhibitor:	0.048
CYP1A2-substrate:	0.082
CYP2C19-inhibitor:	0.033
CYP2C19-substrate:	0.048
CYP2C9-inhibitor:	0.26
CYP2C9-substrate:	0.605
CYP2D6-inhibitor:	0.021
CYP2D6-substrate:	0.193
CYP3A4-inhibitor:	0.032
CYP3A4-substrate:	0.053

ADMET: Excretion

Clearance (CL):	9.352
Half-life (T1/2):	0.935

ADMET: Toxicity

hERG Blockers:	0.017
Human Hepatotoxicity (H-HT):	0.621
Drug-inuced Liver Injury (DILI):	0.147
AMES Toxicity:	0.11
Rat Oral Acute Toxicity:	0.852
Maximum Recommended Daily Dose:	0.046
Skin Sensitization:	0.933
Carcinogencity:	0.206
Eye Corrosion:	0.85
Eye Irritation:	0.965
Respiratory Toxicity:	0.326

Download Data

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

Natural Product: NPC93831

Natural Product ID:	NPC93831
*Common Name:**	2,5-Dihydroxystyrylcarbamic Acid
IUPAC Name:	(E)-3-(2,5-dihydroxyphenyl)prop-2-enoic acid
Synonyms:	2,5-Dihydroxystyrylcarbamic Acid
Standard InCHIKey:	JXIPYOZBOMUUCA-DAFODLJHSA-N
Standard InCHI:	InChI=1S/C9H8O4/c10-7-2-3-8(11)6(5-7)1-4-9(12)13/h1-5,10-11H,(H,12,13)/b4-1+
SMILES:	OC(=O)/C=C/c1cc(O)ccc1O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL450484
PubChem CID:	6442618
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000476] Cinnamic acids and derivatives [CHEMONTID:0001391] Hydroxycinnamic acids and derivatives [CHEMONTID:0002503] Hydroxycinnamic 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
NPO523	Tussilago farfara	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10543912]
NPO523	Tussilago farfara	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[32881525]
NPO523	Tussilago farfara	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO523	Tussilago farfara	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO523	Tussilago farfara	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO523	Tussilago farfara	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO523	Tussilago farfara	Species	Asteraceae	Eukaryota	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	1

Activity Type	# Activity
Individual Protein	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT285	Individual Protein	Epidermal growth factor receptor erbB1	Homo sapiens	IC50	=	8.0	ug.mL-1	PMID[536418]

☑ 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 NPC93831 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	297
0.1-0.2	1928
0.2-0.3	5262
0.3-0.4	13374
0.4-0.5	5582
0.5-0.6	10392
0.6-0.7	4796
0.7-0.8	946
0.8-0.85	93
0.85-0.9	21
0.9-0.95	5
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.932	High Similarity	NPC228609
0.9271	High Similarity	NPC246679
0.9271	High Similarity	NPC257182
0.9057	High Similarity	NPC197513
0.8879	High Similarity	NPC114918
0.8866	High Similarity	NPC29373
0.8857	High Similarity	NPC471535
0.8812	High Similarity	NPC94343
0.8776	High Similarity	NPC81010
0.8776	High Similarity	NPC32977
0.8762	High Similarity	NPC98392
0.8725	High Similarity	NPC470202
0.87	High Similarity	NPC152097
0.87	High Similarity	NPC475078
0.8654	High Similarity	NPC1075
0.8654	High Similarity	NPC1786
0.8654	High Similarity	NPC294902
0.8614	High Similarity	NPC260775
0.86	High Similarity	NPC283711
0.8558	High Similarity	NPC303141
0.8545	High Similarity	NPC163398
0.8545	High Similarity	NPC312800
0.8532	High Similarity	NPC41851
0.8529	High Similarity	NPC130756
0.8529	High Similarity	NPC70677
0.8529	High Similarity	NPC12931
0.8529	High Similarity	NPC130103
0.8529	High Similarity	NPC248396
0.8529	High Similarity	NPC129373
0.8529	High Similarity	NPC48730
0.8515	High Similarity	NPC88420
0.8505	High Similarity	NPC208229
0.8491	Intermediate Similarity	NPC68260
0.8491	Intermediate Similarity	NPC279887
0.8476	Intermediate Similarity	NPC187913
0.8447	Intermediate Similarity	NPC12221
0.8447	Intermediate Similarity	NPC80800
0.8411	Intermediate Similarity	NPC26013
0.8411	Intermediate Similarity	NPC282855
0.8407	Intermediate Similarity	NPC14177
0.8384	Intermediate Similarity	NPC231150
0.8381	Intermediate Similarity	NPC243677
0.8365	Intermediate Similarity	NPC233827
0.8365	Intermediate Similarity	NPC13426
0.8365	Intermediate Similarity	NPC108497
0.835	Intermediate Similarity	NPC253746
0.8348	Intermediate Similarity	NPC477151
0.8348	Intermediate Similarity	NPC132518
0.8333	Intermediate Similarity	NPC140619
0.8304	Intermediate Similarity	NPC278652
0.8304	Intermediate Similarity	NPC160199
0.83	Intermediate Similarity	NPC181709
0.8288	Intermediate Similarity	NPC240163
0.8286	Intermediate Similarity	NPC475580
0.8286	Intermediate Similarity	NPC130817
0.8283	Intermediate Similarity	NPC312304
0.8276	Intermediate Similarity	NPC477153
0.8276	Intermediate Similarity	NPC477152
0.8273	Intermediate Similarity	NPC296144
0.8273	Intermediate Similarity	NPC28784
0.8269	Intermediate Similarity	NPC477685
0.8265	Intermediate Similarity	NPC27974
0.8257	Intermediate Similarity	NPC226250
0.8247	Intermediate Similarity	NPC155393
0.8241	Intermediate Similarity	NPC471954
0.8241	Intermediate Similarity	NPC75272
0.823	Intermediate Similarity	NPC206205
0.8224	Intermediate Similarity	NPC474352
0.8218	Intermediate Similarity	NPC245187
0.8208	Intermediate Similarity	NPC227255
0.8208	Intermediate Similarity	NPC288760
0.8208	Intermediate Similarity	NPC47284
0.8198	Intermediate Similarity	NPC474050
0.8198	Intermediate Similarity	NPC473931
0.8198	Intermediate Similarity	NPC81808
0.8198	Intermediate Similarity	NPC474114
0.819	Intermediate Similarity	NPC304638
0.819	Intermediate Similarity	NPC269212
0.8182	Intermediate Similarity	NPC26615
0.8174	Intermediate Similarity	NPC165197
0.8173	Intermediate Similarity	NPC174911
0.8163	Intermediate Similarity	NPC407
0.8163	Intermediate Similarity	NPC307235
0.8148	Intermediate Similarity	NPC169450
0.8148	Intermediate Similarity	NPC470039
0.8144	Intermediate Similarity	NPC286904
0.8144	Intermediate Similarity	NPC150837
0.8142	Intermediate Similarity	NPC269414
0.8137	Intermediate Similarity	NPC286006
0.8131	Intermediate Similarity	NPC54765
0.8131	Intermediate Similarity	NPC53740
0.8131	Intermediate Similarity	NPC317592
0.8131	Intermediate Similarity	NPC155072
0.8131	Intermediate Similarity	NPC67250
0.8113	Intermediate Similarity	NPC79672
0.8113	Intermediate Similarity	NPC52087
0.8113	Intermediate Similarity	NPC272029
0.8108	Intermediate Similarity	NPC95381
0.8108	Intermediate Similarity	NPC190212
0.8103	Intermediate Similarity	NPC25168
0.81	Intermediate Similarity	NPC192
0.8091	Intermediate Similarity	NPC163674
0.8077	Intermediate Similarity	NPC130193
0.8077	Intermediate Similarity	NPC245561
0.8073	Intermediate Similarity	NPC473524
0.8058	Intermediate Similarity	NPC259512
0.8058	Intermediate Similarity	NPC312132
0.8056	Intermediate Similarity	NPC34715
0.8056	Intermediate Similarity	NPC320439
0.8056	Intermediate Similarity	NPC233320
0.8037	Intermediate Similarity	NPC127676
0.8036	Intermediate Similarity	NPC87563
0.8036	Intermediate Similarity	NPC33749
0.8036	Intermediate Similarity	NPC163154
0.8036	Intermediate Similarity	NPC328593
0.8036	Intermediate Similarity	NPC217472
0.8036	Intermediate Similarity	NPC261453
0.8034	Intermediate Similarity	NPC297193
0.8034	Intermediate Similarity	NPC325301
0.8034	Intermediate Similarity	NPC327070
0.8019	Intermediate Similarity	NPC471228
0.8019	Intermediate Similarity	NPC235762
0.8018	Intermediate Similarity	NPC131530
0.8	Intermediate Similarity	NPC183700
0.8	Intermediate Similarity	NPC95034
0.8	Intermediate Similarity	NPC71525
0.8	Intermediate Similarity	NPC142087
0.8	Intermediate Similarity	NPC72729
0.8	Intermediate Similarity	NPC476020
0.8	Intermediate Similarity	NPC222084
0.8	Intermediate Similarity	NPC52472
0.7982	Intermediate Similarity	NPC95344
0.7982	Intermediate Similarity	NPC125252
0.7982	Intermediate Similarity	NPC206341
0.7982	Intermediate Similarity	NPC100551
0.7981	Intermediate Similarity	NPC6597
0.7981	Intermediate Similarity	NPC156313
0.7981	Intermediate Similarity	NPC474073
0.7981	Intermediate Similarity	NPC79241
0.7981	Intermediate Similarity	NPC201967
0.7966	Intermediate Similarity	NPC248786
0.7965	Intermediate Similarity	NPC233669
0.7965	Intermediate Similarity	NPC474967
0.7963	Intermediate Similarity	NPC19149
0.7963	Intermediate Similarity	NPC469913
0.7961	Intermediate Similarity	NPC274678
0.7946	Intermediate Similarity	NPC98543
0.7944	Intermediate Similarity	NPC475225
0.7941	Intermediate Similarity	NPC147284
0.7941	Intermediate Similarity	NPC55903
0.7941	Intermediate Similarity	NPC306884
0.7941	Intermediate Similarity	NPC162314
0.7941	Intermediate Similarity	NPC3358
0.7941	Intermediate Similarity	NPC210497
0.7941	Intermediate Similarity	NPC94139
0.7931	Intermediate Similarity	NPC260837
0.7928	Intermediate Similarity	NPC297657
0.7921	Intermediate Similarity	NPC47950
0.7913	Intermediate Similarity	NPC309434
0.7913	Intermediate Similarity	NPC275519
0.7913	Intermediate Similarity	NPC203124
0.7909	Intermediate Similarity	NPC316052
0.7909	Intermediate Similarity	NPC79543
0.7905	Intermediate Similarity	NPC33675
0.7905	Intermediate Similarity	NPC299762
0.7905	Intermediate Similarity	NPC171843
0.79	Intermediate Similarity	NPC19680
0.7899	Intermediate Similarity	NPC117794
0.7895	Intermediate Similarity	NPC281277
0.789	Intermediate Similarity	NPC260952
0.789	Intermediate Similarity	NPC141523
0.7881	Intermediate Similarity	NPC46634
0.787	Intermediate Similarity	NPC13495
0.787	Intermediate Similarity	NPC292452
0.7864	Intermediate Similarity	NPC76938
0.7864	Intermediate Similarity	NPC152415
0.7864	Intermediate Similarity	NPC128062
0.7857	Intermediate Similarity	NPC265146
0.785	Intermediate Similarity	NPC168393
0.785	Intermediate Similarity	NPC68269
0.785	Intermediate Similarity	NPC135784
0.7845	Intermediate Similarity	NPC263386
0.7845	Intermediate Similarity	NPC232178
0.7845	Intermediate Similarity	NPC184579
0.7845	Intermediate Similarity	NPC141791
0.7845	Intermediate Similarity	NPC233165
0.7845	Intermediate Similarity	NPC160235
0.7843	Intermediate Similarity	NPC306074
0.7843	Intermediate Similarity	NPC204210
0.7833	Intermediate Similarity	NPC287473
0.7833	Intermediate Similarity	NPC472592
0.7826	Intermediate Similarity	NPC65791
0.7826	Intermediate Similarity	NPC240664
0.7818	Intermediate Similarity	NPC224584
0.7818	Intermediate Similarity	NPC241549
0.781	Intermediate Similarity	NPC109955
0.7807	Intermediate Similarity	NPC161304
0.7805	Intermediate Similarity	NPC31539
0.78	Intermediate Similarity	NPC23167
0.7797	Intermediate Similarity	NPC476165

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 NPC93831 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	263
0.1-0.2	1045
0.2-0.3	1595
0.3-0.4	2977
0.4-0.5	1872
0.5-0.6	1013
0.6-0.7	323
0.7-0.8	59
0.8-0.85	3
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8529	High Similarity	NPD289	Clinical (unspecified phase)
0.8137	Intermediate Similarity	NPD844	Approved
0.8058	Intermediate Similarity	NPD288	Approved
0.8017	Intermediate Similarity	NPD3496	Discontinued
0.7982	Intermediate Similarity	NPD9266	Approved
0.7982	Intermediate Similarity	NPD74	Approved
0.789	Intermediate Similarity	NPD9264	Approved
0.789	Intermediate Similarity	NPD9263	Approved
0.789	Intermediate Similarity	NPD9267	Approved
0.7739	Intermediate Similarity	NPD9493	Approved
0.7727	Intermediate Similarity	NPD9265	Clinical (unspecified phase)
0.7677	Intermediate Similarity	NPD111	Approved
0.7596	Intermediate Similarity	NPD845	Approved
0.7586	Intermediate Similarity	NPD405	Clinical (unspecified phase)
0.7565	Intermediate Similarity	NPD9281	Approved
0.7545	Intermediate Similarity	NPD9697	Approved
0.7544	Intermediate Similarity	NPD7635	Approved
0.7524	Intermediate Similarity	NPD1432	Clinical (unspecified phase)
0.7524	Intermediate Similarity	NPD2933	Approved
0.7524	Intermediate Similarity	NPD2934	Approved
0.7523	Intermediate Similarity	NPD9261	Approved
0.75	Intermediate Similarity	NPD9088	Approved
0.75	Intermediate Similarity	NPD1242	Phase 1
0.75	Intermediate Similarity	NPD6671	Approved
0.7479	Intermediate Similarity	NPD4626	Approved
0.7453	Intermediate Similarity	NPD2860	Approved
0.7453	Intermediate Similarity	NPD2859	Approved
0.7431	Intermediate Similarity	NPD846	Approved
0.7431	Intermediate Similarity	NPD940	Approved
0.7407	Intermediate Similarity	NPD3020	Approved
0.7385	Intermediate Similarity	NPD2935	Discontinued
0.7321	Intermediate Similarity	NPD968	Approved
0.7315	Intermediate Similarity	NPD9273	Approved
0.7311	Intermediate Similarity	NPD9545	Approved
0.7311	Intermediate Similarity	NPD1759	Phase 1
0.7308	Intermediate Similarity	NPD9256	Approved
0.7308	Intermediate Similarity	NPD9258	Approved
0.7295	Intermediate Similarity	NPD9269	Phase 2
0.7295	Intermediate Similarity	NPD9717	Approved
0.729	Intermediate Similarity	NPD1809	Phase 2
0.7281	Intermediate Similarity	NPD3022	Approved
0.7281	Intermediate Similarity	NPD4750	Phase 3
0.7281	Intermediate Similarity	NPD3021	Approved
0.7258	Intermediate Similarity	NPD1203	Approved
0.7258	Intermediate Similarity	NPD1164	Approved
0.7258	Intermediate Similarity	NPD1470	Approved
0.7257	Intermediate Similarity	NPD2342	Discontinued
0.7257	Intermediate Similarity	NPD1358	Approved
0.725	Intermediate Similarity	NPD9268	Approved
0.7227	Intermediate Similarity	NPD1758	Phase 1
0.7213	Intermediate Similarity	NPD422	Phase 1
0.7213	Intermediate Similarity	NPD1611	Approved
0.7213	Intermediate Similarity	NPD1201	Approved
0.7213	Intermediate Similarity	NPD1535	Discovery
0.7209	Intermediate Similarity	NPD447	Suspended
0.719	Intermediate Similarity	NPD1778	Approved
0.7188	Intermediate Similarity	NPD9716	Approved
0.7168	Intermediate Similarity	NPD1445	Approved
0.7168	Intermediate Similarity	NPD3134	Approved
0.7168	Intermediate Similarity	NPD1444	Approved
0.7154	Intermediate Similarity	NPD1481	Phase 2
0.7119	Intermediate Similarity	NPD497	Approved
0.7109	Intermediate Similarity	NPD411	Approved
0.7107	Intermediate Similarity	NPD5691	Approved
0.7083	Intermediate Similarity	NPD9087	Approved
0.7069	Intermediate Similarity	NPD9280	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD255	Approved
0.7059	Intermediate Similarity	NPD256	Approved
0.7054	Intermediate Similarity	NPD9500	Approved
0.704	Intermediate Similarity	NPD3225	Approved
0.7034	Intermediate Similarity	NPD498	Approved
0.7034	Intermediate Similarity	NPD496	Approved
0.7034	Intermediate Similarity	NPD495	Approved
0.7009	Intermediate Similarity	NPD228	Approved
0.7	Intermediate Similarity	NPD9568	Approved
0.6983	Remote Similarity	NPD1792	Phase 2
0.6975	Remote Similarity	NPD9614	Approved
0.6975	Remote Similarity	NPD9618	Approved
0.696	Remote Similarity	NPD4379	Clinical (unspecified phase)
0.6949	Remote Similarity	NPD9377	Approved
0.6949	Remote Similarity	NPD9379	Approved
0.6947	Remote Similarity	NPD230	Phase 1
0.6944	Remote Similarity	NPD1202	Approved
0.6929	Remote Similarity	NPD258	Approved
0.6929	Remote Similarity	NPD257	Approved
0.6923	Remote Similarity	NPD9257	Approved
0.6923	Remote Similarity	NPD520	Approved
0.6923	Remote Similarity	NPD9259	Approved
0.6887	Remote Similarity	NPD9295	Approved
0.6875	Remote Similarity	NPD9569	Approved
0.687	Remote Similarity	NPD943	Approved
0.687	Remote Similarity	NPD4060	Phase 1
0.6869	Remote Similarity	NPD9294	Approved
0.6866	Remote Similarity	NPD5404	Approved
0.6866	Remote Similarity	NPD5406	Approved
0.6866	Remote Similarity	NPD5408	Approved
0.6866	Remote Similarity	NPD5405	Approved
0.685	Remote Similarity	NPD2797	Approved
0.6847	Remote Similarity	NPD9495	Approved
0.6846	Remote Similarity	NPD2313	Discontinued
0.6846	Remote Similarity	NPD3764	Approved
0.6842	Remote Similarity	NPD9610	Approved
0.6842	Remote Similarity	NPD9608	Approved
0.6829	Remote Similarity	NPD4196	Clinical (unspecified phase)
0.6815	Remote Similarity	NPD7266	Discontinued
0.681	Remote Similarity	NPD290	Approved
0.6809	Remote Similarity	NPD1653	Approved
0.6803	Remote Similarity	NPD9613	Approved
0.6803	Remote Similarity	NPD9615	Approved
0.6803	Remote Similarity	NPD9616	Approved
0.6796	Remote Similarity	NPD9491	Approved
0.6791	Remote Similarity	NPD651	Clinical (unspecified phase)
0.6777	Remote Similarity	NPD709	Approved
0.6774	Remote Similarity	NPD2932	Approved
0.6774	Remote Similarity	NPD3019	Approved
0.6765	Remote Similarity	NPD226	Approved
0.6752	Remote Similarity	NPD6831	Clinical (unspecified phase)
0.6748	Remote Similarity	NPD316	Approved
0.6748	Remote Similarity	NPD2226	Clinical (unspecified phase)
0.6746	Remote Similarity	NPD1608	Approved
0.6744	Remote Similarity	NPD2861	Phase 2
0.6744	Remote Similarity	NPD5736	Approved
0.6741	Remote Similarity	NPD1551	Phase 2
0.6739	Remote Similarity	NPD6190	Approved
0.6726	Remote Similarity	NPD3028	Approved
0.6723	Remote Similarity	NPD969	Suspended
0.6723	Remote Similarity	NPD6124	Clinical (unspecified phase)
0.6718	Remote Similarity	NPD3268	Approved
0.6699	Remote Similarity	NPD9089	Approved
0.6695	Remote Similarity	NPD9380	Clinical (unspecified phase)
0.6694	Remote Similarity	NPD1791	Approved
0.6694	Remote Similarity	NPD5585	Approved
0.6694	Remote Similarity	NPD1476	Clinical (unspecified phase)
0.6694	Remote Similarity	NPD1793	Approved
0.6693	Remote Similarity	NPD3600	Clinical (unspecified phase)
0.6692	Remote Similarity	NPD1899	Clinical (unspecified phase)
0.6691	Remote Similarity	NPD2346	Discontinued
0.6667	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD259	Phase 1
0.6667	Remote Similarity	NPD1019	Discontinued
0.6667	Remote Similarity	NPD5535	Approved
0.6667	Remote Similarity	NPD4308	Phase 3
0.6667	Remote Similarity	NPD5536	Phase 2
0.6642	Remote Similarity	NPD970	Clinical (unspecified phase)
0.6641	Remote Similarity	NPD1283	Approved
0.6641	Remote Similarity	NPD9537	Phase 1
0.6641	Remote Similarity	NPD9536	Phase 1
0.6641	Remote Similarity	NPD6696	Suspended
0.664	Remote Similarity	NPD9381	Approved
0.664	Remote Similarity	NPD9384	Approved
0.6637	Remote Similarity	NPD9712	Approved
0.6617	Remote Similarity	NPD6346	Approved
0.6617	Remote Similarity	NPD825	Approved
0.6617	Remote Similarity	NPD826	Approved
0.6615	Remote Similarity	NPD2237	Approved
0.6615	Remote Similarity	NPD9494	Approved
0.6613	Remote Similarity	NPD3091	Approved
0.6612	Remote Similarity	NPD2228	Approved
0.6612	Remote Similarity	NPD2229	Approved
0.6612	Remote Similarity	NPD2234	Approved
0.6612	Remote Similarity	NPD1398	Phase 1
0.6612	Remote Similarity	NPD7159	Clinical (unspecified phase)
0.6609	Remote Similarity	NPD6647	Phase 2
0.6602	Remote Similarity	NPD9093	Approved
0.6587	Remote Similarity	NPD1980	Approved
0.6587	Remote Similarity	NPD1981	Approved
0.6587	Remote Similarity	NPD1983	Approved
0.6587	Remote Similarity	NPD3847	Discontinued
0.6583	Remote Similarity	NPD9508	Approved
0.6567	Remote Similarity	NPD274	Approved
0.6567	Remote Similarity	NPD555	Phase 2
0.6567	Remote Similarity	NPD275	Approved
0.6565	Remote Similarity	NPD1529	Clinical (unspecified phase)
0.6565	Remote Similarity	NPD596	Approved
0.6565	Remote Similarity	NPD600	Approved
0.6562	Remote Similarity	NPD1755	Approved
0.6557	Remote Similarity	NPD690	Clinical (unspecified phase)
0.6552	Remote Similarity	NPD164	Approved
0.6552	Remote Similarity	NPD1237	Approved
0.6549	Remote Similarity	NPD9710	Approved
0.6549	Remote Similarity	NPD9711	Approved
0.6547	Remote Similarity	NPD8166	Discontinued
0.6547	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.6547	Remote Similarity	NPD3750	Approved
0.6544	Remote Similarity	NPD2799	Discontinued
0.6544	Remote Similarity	NPD1509	Clinical (unspecified phase)
0.6544	Remote Similarity	NPD3299	Clinical (unspecified phase)
0.6541	Remote Similarity	NPD840	Approved
0.6541	Remote Similarity	NPD839	Approved
0.6541	Remote Similarity	NPD6663	Approved
0.6538	Remote Similarity	NPD2798	Approved
0.6535	Remote Similarity	NPD1091	Approved
0.6519	Remote Similarity	NPD6653	Approved
0.6515	Remote Similarity	NPD7095	Approved
0.6508	Remote Similarity	NPD17	Approved
0.6508	Remote Similarity	NPD4059	Approved
0.6508	Remote Similarity	NPD2286	Discontinued
0.6496	Remote Similarity	NPD9570	Approved
0.6496	Remote Similarity	NPD6032	Approved
0.6493	Remote Similarity	NPD468	Phase 1

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