NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	245.11
Volume:	255.136
LogP:	1.433
LogD:	1.77
LogS:	-1.596
# Rotatable Bonds:	5
TPSA:	62.46
# H-Bond Aceptor:	4
# H-Bond Donor:	2
# Rings:	2
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.787
Synthetic Accessibility Score:	2.281
Fsp3:	0.214
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:	-4.564
MDCK Permeability:	1.2821004929719493e-05
Pgp-inhibitor:	0.006
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.199
20% Bioavailability (F20%):	0.925
30% Bioavailability (F30%):	0.538

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.224
Plasma Protein Binding (PPB):	40.6809196472168%
Volume Distribution (VD):	1.293
Pgp-substrate:	55.75544357299805%

ADMET: Metabolism

CYP1A2-inhibitor:	0.81
CYP1A2-substrate:	0.098
CYP2C19-inhibitor:	0.64
CYP2C19-substrate:	0.083
CYP2C9-inhibitor:	0.412
CYP2C9-substrate:	0.198
CYP2D6-inhibitor:	0.332
CYP2D6-substrate:	0.769
CYP3A4-inhibitor:	0.109
CYP3A4-substrate:	0.269

ADMET: Excretion

Clearance (CL):	9.819
Half-life (T1/2):	0.896

ADMET: Toxicity

hERG Blockers:	0.036
Human Hepatotoxicity (H-HT):	0.096
Drug-inuced Liver Injury (DILI):	0.87
AMES Toxicity:	0.669
Rat Oral Acute Toxicity:	0.173
Maximum Recommended Daily Dose:	0.051
Skin Sensitization:	0.497
Carcinogencity:	0.34
Eye Corrosion:	0.004
Eye Irritation:	0.563
Respiratory Toxicity:	0.157

Download Data

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

Natural Product: NPC295158

Natural Product ID:	NPC295158
*Common Name:**	Fusarine
IUPAC Name:	2-hydroxy-1-[1-[2-(4-hydroxyphenyl)ethyl]pyrrol-2-yl]ethanone
Synonyms:	Fusarine
Standard InCHIKey:	JYXGPDOHRYTOBE-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C14H15NO3/c16-10-14(18)13-2-1-8-15(13)9-7-11-3-5-12(17)6-4-11/h1-6,8,16-17H,7,9-10H2
SMILES:	c1cc(C(=O)CO)n(c1)CCc1ccc(cc1)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2036493
PubChem CID:	57408890
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0004603] Organic oxygen compounds [CHEMONTID:0000323] Organooxygen compounds [CHEMONTID:0001831] Carbonyl compounds [CHEMONTID:0000118] Ketones [CHEMONTID:0003670] Aryl ketones [CHEMONTID:0003671] Aryl alkyl ketones

*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
NPO24024	Fusarium semitectum	Species	Nectriaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10978211]
NPO24024	Fusarium semitectum	Species	Nectriaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22439674]
NPO24024	Fusarium semitectum	Species	Nectriaceae	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
GI50	2
Others	1

Activity Type	# Activity
Cell Line	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT111	Cell Line	K562	Homo sapiens	GI50	>	200000.0	nM	PMID[545955]
NPT737	Cell Line	HUVEC	Homo sapiens	GI50	>	200000.0	nM	PMID[545955]
NPT165	Cell Line	HeLa	Homo sapiens	CC50	>	200000.0	nM	PMID[545955]

☑ 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 NPC295158 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	315
0.1-0.2	3135
0.2-0.3	13321
0.3-0.4	5453
0.4-0.5	15194
0.5-0.6	3135
0.6-0.7	1912
0.7-0.8	219
0.8-0.85	8
0.85-0.9	4
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.8851	High Similarity	NPC241025
0.8571	High Similarity	NPC78767
0.8571	High Similarity	NPC473814
0.8564	High Similarity	NPC93390
0.8424	Intermediate Similarity	NPC472284
0.8407	Intermediate Similarity	NPC473821
0.837	Intermediate Similarity	NPC74153
0.8115	Intermediate Similarity	NPC472287
0.8115	Intermediate Similarity	NPC472286
0.7967	Intermediate Similarity	NPC207851
0.7887	Intermediate Similarity	NPC183777
0.7868	Intermediate Similarity	NPC219087
0.7806	Intermediate Similarity	NPC61038
0.7797	Intermediate Similarity	NPC41717
0.7772	Intermediate Similarity	NPC54066
0.7744	Intermediate Similarity	NPC175602
0.7711	Intermediate Similarity	NPC27041
0.7692	Intermediate Similarity	NPC472259
0.7672	Intermediate Similarity	NPC471448
0.765	Intermediate Similarity	NPC207866
0.7609	Intermediate Similarity	NPC271792
0.7604	Intermediate Similarity	NPC90229
0.7596	Intermediate Similarity	NPC96890
0.7576	Intermediate Similarity	NPC171787
0.7551	Intermediate Similarity	NPC53144
0.7549	Intermediate Similarity	NPC168209
0.7525	Intermediate Similarity	NPC88008
0.7514	Intermediate Similarity	NPC113812
0.7512	Intermediate Similarity	NPC110182
0.7512	Intermediate Similarity	NPC14686
0.75	Intermediate Similarity	NPC146724
0.7487	Intermediate Similarity	NPC56170
0.7474	Intermediate Similarity	NPC154339
0.7473	Intermediate Similarity	NPC273532
0.7473	Intermediate Similarity	NPC253810
0.7463	Intermediate Similarity	NPC269270
0.746	Intermediate Similarity	NPC46580
0.7444	Intermediate Similarity	NPC471178
0.7443	Intermediate Similarity	NPC263455
0.744	Intermediate Similarity	NPC175150
0.744	Intermediate Similarity	NPC243633
0.7435	Intermediate Similarity	NPC114974
0.743	Intermediate Similarity	NPC124542
0.743	Intermediate Similarity	NPC59779
0.743	Intermediate Similarity	NPC471177
0.7421	Intermediate Similarity	NPC209917
0.7419	Intermediate Similarity	NPC52831
0.7419	Intermediate Similarity	NPC325705
0.7411	Intermediate Similarity	NPC57398
0.7399	Intermediate Similarity	NPC302159
0.7398	Intermediate Similarity	NPC213308
0.7398	Intermediate Similarity	NPC315491
0.7398	Intermediate Similarity	NPC45459
0.7379	Intermediate Similarity	NPC313804
0.7379	Intermediate Similarity	NPC315804
0.7376	Intermediate Similarity	NPC146418
0.7374	Intermediate Similarity	NPC200836
0.7368	Intermediate Similarity	NPC278434
0.7366	Intermediate Similarity	NPC164340
0.7366	Intermediate Similarity	NPC472285
0.7358	Intermediate Similarity	NPC267343
0.7353	Intermediate Similarity	NPC237740
0.7337	Intermediate Similarity	NPC472288
0.7327	Intermediate Similarity	NPC309845
0.7327	Intermediate Similarity	NPC85273
0.7323	Intermediate Similarity	NPC211813
0.7312	Intermediate Similarity	NPC184964
0.7296	Intermediate Similarity	NPC474916
0.7295	Intermediate Similarity	NPC74360
0.7293	Intermediate Similarity	NPC102423
0.7292	Intermediate Similarity	NPC83111
0.7288	Intermediate Similarity	NPC312860
0.7277	Intermediate Similarity	NPC238242
0.7277	Intermediate Similarity	NPC206186
0.7264	Intermediate Similarity	NPC193238
0.7263	Intermediate Similarity	NPC282103
0.7263	Intermediate Similarity	NPC314002
0.726	Intermediate Similarity	NPC276657
0.7259	Intermediate Similarity	NPC81535
0.725	Intermediate Similarity	NPC477043
0.7249	Intermediate Similarity	NPC220765
0.7246	Intermediate Similarity	NPC264285
0.7245	Intermediate Similarity	NPC156704
0.7243	Intermediate Similarity	NPC200553
0.7243	Intermediate Similarity	NPC279189
0.7241	Intermediate Similarity	NPC167400
0.724	Intermediate Similarity	NPC44354
0.7234	Intermediate Similarity	NPC317010
0.7234	Intermediate Similarity	NPC73994
0.7233	Intermediate Similarity	NPC322064
0.7228	Intermediate Similarity	NPC473764
0.7228	Intermediate Similarity	NPC314940
0.7225	Intermediate Similarity	NPC171171
0.7222	Intermediate Similarity	NPC80681
0.722	Intermediate Similarity	NPC236668
0.7216	Intermediate Similarity	NPC99666
0.7211	Intermediate Similarity	NPC204717
0.7202	Intermediate Similarity	NPC144381
0.72	Intermediate Similarity	NPC220523
0.72	Intermediate Similarity	NPC161292
0.7198	Intermediate Similarity	NPC473057
0.7184	Intermediate Similarity	NPC146976
0.7183	Intermediate Similarity	NPC246381
0.7179	Intermediate Similarity	NPC230403
0.7178	Intermediate Similarity	NPC316403
0.7178	Intermediate Similarity	NPC53344
0.7178	Intermediate Similarity	NPC270918
0.7172	Intermediate Similarity	NPC474767
0.7171	Intermediate Similarity	NPC12344
0.7164	Intermediate Similarity	NPC470500
0.7164	Intermediate Similarity	NPC210256
0.7159	Intermediate Similarity	NPC100726
0.7156	Intermediate Similarity	NPC122436
0.7151	Intermediate Similarity	NPC33229
0.7151	Intermediate Similarity	NPC63562
0.7151	Intermediate Similarity	NPC209362
0.715	Intermediate Similarity	NPC75544
0.715	Intermediate Similarity	NPC328596
0.715	Intermediate Similarity	NPC328318
0.7143	Intermediate Similarity	NPC477549
0.7143	Intermediate Similarity	NPC210828
0.7143	Intermediate Similarity	NPC473317
0.7143	Intermediate Similarity	NPC256893
0.7143	Intermediate Similarity	NPC162002
0.7143	Intermediate Similarity	NPC86834
0.7143	Intermediate Similarity	NPC326634
0.7143	Intermediate Similarity	NPC61011
0.7135	Intermediate Similarity	NPC472260
0.7135	Intermediate Similarity	NPC118084
0.7135	Intermediate Similarity	NPC114310
0.713	Intermediate Similarity	NPC172222
0.7128	Intermediate Similarity	NPC324149
0.7126	Intermediate Similarity	NPC71236
0.7121	Intermediate Similarity	NPC212213
0.712	Intermediate Similarity	NPC114637
0.712	Intermediate Similarity	NPC46895
0.7114	Intermediate Similarity	NPC134848
0.7112	Intermediate Similarity	NPC303225
0.7107	Intermediate Similarity	NPC109922
0.7101	Intermediate Similarity	NPC50562
0.71	Intermediate Similarity	NPC155792
0.7098	Intermediate Similarity	NPC36498
0.7097	Intermediate Similarity	NPC174489
0.7097	Intermediate Similarity	NPC302647
0.709	Intermediate Similarity	NPC42979
0.7088	Intermediate Similarity	NPC322644
0.7088	Intermediate Similarity	NPC25899
0.7088	Intermediate Similarity	NPC131718
0.7086	Intermediate Similarity	NPC159630
0.7086	Intermediate Similarity	NPC230085
0.7083	Intermediate Similarity	NPC207686
0.7079	Intermediate Similarity	NPC473878
0.7077	Intermediate Similarity	NPC138370
0.7074	Intermediate Similarity	NPC224764
0.7073	Intermediate Similarity	NPC470020
0.7072	Intermediate Similarity	NPC269919
0.7072	Intermediate Similarity	NPC132680
0.7068	Intermediate Similarity	NPC159125
0.7067	Intermediate Similarity	NPC67658
0.7067	Intermediate Similarity	NPC62995
0.7059	Intermediate Similarity	NPC39679
0.7059	Intermediate Similarity	NPC313791
0.7056	Intermediate Similarity	NPC202812
0.7056	Intermediate Similarity	NPC186351
0.7053	Intermediate Similarity	NPC471997
0.7053	Intermediate Similarity	NPC24864
0.7049	Intermediate Similarity	NPC48192
0.7049	Intermediate Similarity	NPC242116
0.7047	Intermediate Similarity	NPC315555
0.7047	Intermediate Similarity	NPC194040
0.7042	Intermediate Similarity	NPC125597
0.7039	Intermediate Similarity	NPC217021
0.7039	Intermediate Similarity	NPC23294
0.7039	Intermediate Similarity	NPC284348
0.7039	Intermediate Similarity	NPC470679
0.7039	Intermediate Similarity	NPC153769
0.7037	Intermediate Similarity	NPC83774
0.7035	Intermediate Similarity	NPC477044
0.7035	Intermediate Similarity	NPC306376
0.7035	Intermediate Similarity	NPC477041
0.7032	Intermediate Similarity	NPC26641
0.7028	Intermediate Similarity	NPC16352
0.7024	Intermediate Similarity	NPC325297
0.7024	Intermediate Similarity	NPC174758
0.7021	Intermediate Similarity	NPC469529
0.7021	Intermediate Similarity	NPC139763
0.702	Intermediate Similarity	NPC251090
0.7018	Intermediate Similarity	NPC182222
0.7018	Intermediate Similarity	NPC475635
0.7014	Intermediate Similarity	NPC210296
0.701	Intermediate Similarity	NPC321428
0.7009	Intermediate Similarity	NPC24370
0.7009	Intermediate Similarity	NPC319232
0.7005	Intermediate Similarity	NPC252590
0.7005	Intermediate Similarity	NPC249614
0.7	Intermediate Similarity	NPC55772
0.7	Intermediate Similarity	NPC107287
0.7	Intermediate Similarity	NPC123395
0.6995	Remote Similarity	NPC324203
0.6995	Remote Similarity	NPC63338

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 NPC295158 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	204
0.1-0.2	679
0.2-0.3	831
0.3-0.4	1066
0.4-0.5	2994
0.5-0.6	2434
0.6-0.7	891
0.7-0.8	51
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
0.78	Intermediate Similarity	NPD3326	Clinical (unspecified phase)
0.7784	Intermediate Similarity	NPD1631	Approved
0.774	Intermediate Similarity	NPD1568	Clinical (unspecified phase)
0.7709	Intermediate Similarity	NPD1575	Approved
0.7709	Intermediate Similarity	NPD1573	Approved
0.7614	Intermediate Similarity	NPD1630	Approved
0.7486	Intermediate Similarity	NPD4736	Clinical (unspecified phase)
0.7473	Intermediate Similarity	NPD3178	Discontinued
0.7426	Intermediate Similarity	NPD5866	Approved
0.7419	Intermediate Similarity	NPD9510	Approved
0.7419	Intermediate Similarity	NPD1643	Phase 3
0.7398	Intermediate Similarity	NPD484	Approved
0.738	Intermediate Similarity	NPD1783	Clinical (unspecified phase)
0.7366	Intermediate Similarity	NPD1587	Approved
0.7311	Intermediate Similarity	NPD5801	Clinical (unspecified phase)
0.7299	Intermediate Similarity	NPD4845	Discontinued
0.7286	Intermediate Similarity	NPD5513	Phase 2
0.7268	Intermediate Similarity	NPD6872	Clinical (unspecified phase)
0.7268	Intermediate Similarity	NPD2781	Approved
0.7259	Intermediate Similarity	NPD6137	Clinical (unspecified phase)
0.7253	Intermediate Similarity	NPD2782	Approved
0.7253	Intermediate Similarity	NPD2780	Approved
0.7241	Intermediate Similarity	NPD9075	Approved
0.7241	Intermediate Similarity	NPD9074	Approved
0.7219	Intermediate Similarity	NPD5751	Clinical (unspecified phase)
0.7211	Intermediate Similarity	NPD1096	Discontinued
0.7206	Intermediate Similarity	NPD3779	Clinical (unspecified phase)
0.7204	Intermediate Similarity	NPD1586	Approved
0.7198	Intermediate Similarity	NPD5088	Discontinued
0.719	Intermediate Similarity	NPD8356	Approved
0.7143	Intermediate Similarity	NPD3395	Approved
0.7143	Intermediate Similarity	NPD3396	Approved
0.7129	Intermediate Similarity	NPD7203	Clinical (unspecified phase)
0.7128	Intermediate Similarity	NPD6569	Phase 2
0.7115	Intermediate Similarity	NPD4989	Phase 2
0.7098	Intermediate Similarity	NPD9363	Approved
0.7098	Intermediate Similarity	NPD9364	Phase 2
0.7083	Intermediate Similarity	NPD6344	Clinical (unspecified phase)
0.7079	Intermediate Similarity	NPD3947	Discontinued
0.7072	Intermediate Similarity	NPD9383	Approved
0.7072	Intermediate Similarity	NPD9382	Approved
0.7071	Intermediate Similarity	NPD7948	Phase 1
0.7065	Intermediate Similarity	NPD6975	Discontinued
0.7056	Intermediate Similarity	NPD5975	Clinical (unspecified phase)
0.7056	Intermediate Similarity	NPD8430	Approved
0.7051	Intermediate Similarity	NPD5040	Clinical (unspecified phase)
0.7047	Intermediate Similarity	NPD3315	Phase 3
0.7044	Intermediate Similarity	NPD6732	Clinical (unspecified phase)
0.7039	Intermediate Similarity	NPD9706	Clinical (unspecified phase)
0.7026	Intermediate Similarity	NPD3321	Discontinued
0.7021	Intermediate Similarity	NPD9690	Approved
0.7014	Intermediate Similarity	NPD8479	Phase 2
0.7011	Intermediate Similarity	NPD107	Approved
0.7009	Intermediate Similarity	NPD5640	Discontinued
0.7005	Intermediate Similarity	NPD5575	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD180	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD8405	Clinical (unspecified phase)
0.6995	Remote Similarity	NPD112	Approved
0.6995	Remote Similarity	NPD6987	Phase 1
0.6995	Remote Similarity	NPD2511	Approved
0.6995	Remote Similarity	NPD9398	Clinical (unspecified phase)
0.6995	Remote Similarity	NPD9705	Discontinued
0.6995	Remote Similarity	NPD5901	Discontinued
0.6976	Remote Similarity	NPD6376	Discontinued
0.6973	Remote Similarity	NPD926	Approved
0.6973	Remote Similarity	NPD925	Approved
0.6968	Remote Similarity	NPD750	Phase 2
0.6965	Remote Similarity	NPD4396	Clinical (unspecified phase)
0.6961	Remote Similarity	NPD7001	Phase 3
0.6954	Remote Similarity	NPD981	Phase 2
0.6944	Remote Similarity	NPD5965	Clinical (unspecified phase)
0.694	Remote Similarity	NPD5255	Approved
0.6937	Remote Similarity	NPD6790	Phase 1
0.6934	Remote Similarity	NPD6242	Discontinued
0.6927	Remote Similarity	NPD9362	Approved
0.6927	Remote Similarity	NPD7414	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD4948	Discontinued
0.6916	Remote Similarity	NPD7547	Clinical (unspecified phase)
0.6912	Remote Similarity	NPD6138	Clinical (unspecified phase)
0.6911	Remote Similarity	NPD1620	Clinical (unspecified phase)
0.6907	Remote Similarity	NPD4889	Approved
0.6905	Remote Similarity	NPD2412	Clinical (unspecified phase)
0.6898	Remote Similarity	NPD3259	Approved
0.6897	Remote Similarity	NPD203	Clinical (unspecified phase)
0.6897	Remote Similarity	NPD2896	Discontinued
0.6893	Remote Similarity	NPD3813	Approved
0.6885	Remote Similarity	NPD820	Phase 3
0.6872	Remote Similarity	NPD9271	Approved
0.6863	Remote Similarity	NPD2121	Clinical (unspecified phase)
0.6857	Remote Similarity	NPD569	Clinical (unspecified phase)
0.6854	Remote Similarity	NPD7180	Phase 3
0.6853	Remote Similarity	NPD1213	Phase 3
0.685	Remote Similarity	NPD2290	Phase 3
0.685	Remote Similarity	NPD2289	Phase 3
0.6849	Remote Similarity	NPD7031	Phase 1
0.6848	Remote Similarity	NPD604	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD7069	Discontinued
0.684	Remote Similarity	NPD2011	Clinical (unspecified phase)
0.6837	Remote Similarity	NPD2383	Phase 1
0.6834	Remote Similarity	NPD802	Phase 2
0.6834	Remote Similarity	NPD1038	Approved
0.6832	Remote Similarity	NPD6999	Discontinued
0.6832	Remote Similarity	NPD7000	Clinical (unspecified phase)
0.6829	Remote Similarity	NPD2831	Approved
0.6827	Remote Similarity	NPD3392	Approved
0.6825	Remote Similarity	NPD2433	Clinical (unspecified phase)
0.6825	Remote Similarity	NPD3393	Approved
0.6825	Remote Similarity	NPD3389	Approved
0.6825	Remote Similarity	NPD3394	Approved
0.6823	Remote Similarity	NPD8304	Clinical (unspecified phase)
0.6821	Remote Similarity	NPD2814	Clinical (unspecified phase)
0.6812	Remote Similarity	NPD2510	Approved
0.6812	Remote Similarity	NPD7467	Discontinued
0.6812	Remote Similarity	NPD2509	Approved
0.6806	Remote Similarity	NPD3004	Clinical (unspecified phase)
0.6802	Remote Similarity	NPD1627	Clinical (unspecified phase)
0.6802	Remote Similarity	NPD4021	Phase 2
0.6798	Remote Similarity	NPD6389	Clinical (unspecified phase)
0.6798	Remote Similarity	NPD5228	Phase 3
0.6793	Remote Similarity	NPD2582	Approved
0.6793	Remote Similarity	NPD2581	Approved
0.6784	Remote Similarity	NPD6665	Discontinued
0.678	Remote Similarity	NPD5020	Approved
0.6778	Remote Similarity	NPD4703	Approved
0.6778	Remote Similarity	NPD4702	Approved
0.6777	Remote Similarity	NPD4897	Phase 2
0.6774	Remote Similarity	NPD7603	Discontinued
0.6757	Remote Similarity	NPD704	Clinical (unspecified phase)
0.6755	Remote Similarity	NPD424	Approved
0.6755	Remote Similarity	NPD425	Approved
0.6754	Remote Similarity	NPD482	Approved
0.6754	Remote Similarity	NPD158	Discontinued
0.6754	Remote Similarity	NPD5065	Approved
0.6753	Remote Similarity	NPD3386	Phase 2
0.6753	Remote Similarity	NPD4011	Clinical (unspecified phase)
0.675	Remote Similarity	NPD1173	Approved
0.675	Remote Similarity	NPD4551	Phase 2
0.6748	Remote Similarity	NPD6323	Clinical (unspecified phase)
0.6748	Remote Similarity	NPD3397	Phase 2
0.6744	Remote Similarity	NPD4923	Phase 1
0.6743	Remote Similarity	NPD9506	Approved
0.6743	Remote Similarity	NPD7994	Phase 2
0.6743	Remote Similarity	NPD7268	Clinical (unspecified phase)
0.6742	Remote Similarity	NPD4373	Phase 2
0.6735	Remote Similarity	NPD5555	Phase 1
0.6734	Remote Similarity	NPD2336	Approved
0.6733	Remote Similarity	NPD1229	Phase 2
0.6728	Remote Similarity	NPD7586	Clinical (unspecified phase)
0.6725	Remote Similarity	NPD6525	Clinical (unspecified phase)
0.672	Remote Similarity	NPD4639	Approved
0.672	Remote Similarity	NPD4640	Approved
0.672	Remote Similarity	NPD4638	Approved
0.6719	Remote Similarity	NPD749	Clinical (unspecified phase)
0.6716	Remote Similarity	NPD5497	Clinical (unspecified phase)
0.6716	Remote Similarity	NPD4491	Clinical (unspecified phase)
0.6715	Remote Similarity	NPD7568	Phase 1
0.6714	Remote Similarity	NPD6710	Phase 3
0.6706	Remote Similarity	NPD9284	Approved
0.6701	Remote Similarity	NPD5898	Approved
0.6701	Remote Similarity	NPD5899	Approved
0.6701	Remote Similarity	NPD4375	Approved
0.6701	Remote Similarity	NPD5897	Approved
0.67	Remote Similarity	NPD4376	Phase 3
0.6697	Remote Similarity	NPD3960	Clinical (unspecified phase)
0.6696	Remote Similarity	NPD6825	Phase 1
0.6685	Remote Similarity	NPD1270	Approved
0.6685	Remote Similarity	NPD2809	Approved
0.6684	Remote Similarity	NPD3569	Discontinued
0.6683	Remote Similarity	NPD1392	Approved
0.6683	Remote Similarity	NPD3871	Clinical (unspecified phase)
0.6683	Remote Similarity	NPD5017	Discontinued
0.6683	Remote Similarity	NPD3870	Clinical (unspecified phase)
0.6682	Remote Similarity	NPD4429	Discontinued
0.6682	Remote Similarity	NPD7853	Phase 2
0.6682	Remote Similarity	NPD4952	Phase 3
0.6682	Remote Similarity	NPD3354	Phase 2
0.6682	Remote Similarity	NPD6568	Discontinued
0.6682	Remote Similarity	NPD5022	Discontinued
0.6682	Remote Similarity	NPD1659	Phase 1
0.6667	Remote Similarity	NPD4529	Approved
0.6667	Remote Similarity	NPD32	Approved
0.6667	Remote Similarity	NPD31	Approved
0.6667	Remote Similarity	NPD7712	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD4122	Approved
0.6667	Remote Similarity	NPD4036	Approved
0.6667	Remote Similarity	NPD4033	Approved
0.6667	Remote Similarity	NPD5612	Discontinued
0.6667	Remote Similarity	NPD4038	Approved
0.6667	Remote Similarity	NPD4035	Approved
0.6667	Remote Similarity	NPD1034	Phase 3
0.6667	Remote Similarity	NPD2921	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD4528	Approved
0.6667	Remote Similarity	NPD4174	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD9695	Approved
0.6667	Remote Similarity	NPD1033	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD4034	Approved
0.6667	Remote Similarity	NPD4526	Approved
0.6667	Remote Similarity	NPD1923	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD4037	Approved
0.6667	Remote Similarity	NPD4039	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