NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	109.05
Volume:	115.654
LogP:	0.967
LogD:	1.082
LogS:	-1.044
# Rotatable Bonds:	1
TPSA:	22
# H-Bond Aceptor:	2
# H-Bond Donor:	0
# Rings:	1
# Heavy Atoms:	2

MedChem Properties

QED Drug-Likeness Score:	0.49
Synthetic Accessibility Score:	2.613
Fsp3:	0.167
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:	-4.524
MDCK Permeability:	2.35E-05
Pgp-inhibitor:	0
Pgp-substrate:	0.003
Human Intestinal Absorption (HIA):	0.053
20% Bioavailability (F20%):	0.004
30% Bioavailability (F30%):	0.01

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.897
Plasma Protein Binding (PPB):	23.51%
Volume Distribution (VD):	1.724
Pgp-substrate:	76.75%

ADMET: Metabolism

CYP1A2-inhibitor:	0.897
CYP1A2-substrate:	0.757
CYP2C19-inhibitor:	0.099
CYP2C19-substrate:	0.53
CYP2C9-inhibitor:	0.015
CYP2C9-substrate:	0.262
CYP2D6-inhibitor:	0.003
CYP2D6-substrate:	0.501
CYP3A4-inhibitor:	0.008
CYP3A4-substrate:	0.246

ADMET: Excretion

Clearance (CL):	9.187
Half-life (T1/2):	0.839

ADMET: Toxicity

hERG Blockers:	0.007
Human Hepatotoxicity (H-HT):	0.102
Drug-inuced Liver Injury (DILI):	0.039
AMES Toxicity:	0.05
Rat Oral Acute Toxicity:	0.075
Maximum Recommended Daily Dose:	0.115
Skin Sensitization:	0.105
Carcinogencity:	0.224
Eye Corrosion:	0.438
Eye Irritation:	0.893
Respiratory Toxicity:	0.783

Download Data

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

Natural Product: NPC71236

Natural Product ID:	NPC71236
*Common Name:**	1-Methylpyrrole-2-Carbaldehyde
IUPAC Name:	1-methylpyrrole-2-carbaldehyde
Synonyms:
Standard InCHIKey:	OUKQTRFCDKSEPL-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C6H7NO/c1-7-4-2-3-6(7)5-8/h2-5H,1H3
SMILES:	O=Cc1cccn1C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2229659
PubChem CID:	14504
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0004603] Organic oxygen compounds [CHEMONTID:0000323] Organooxygen compounds [CHEMONTID:0001831] Carbonyl compounds [CHEMONTID:0000124] Aldehydes [CHEMONTID:0003213] Aryl-aldehydes

*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
NPO1099	Capparis spinosa	Species	Capparaceae	Eukaryota	aerial parts and buds	Cagliari, Sardinia	2012-FEB	PMID[22769561]
NPO1099	Capparis spinosa	Species	Capparaceae	Eukaryota	Flower	n.a.	n.a.	Database[FooDB]
NPO1099	Capparis spinosa	Species	Capparaceae	Eukaryota	Fruit	n.a.	n.a.	Database[FooDB]
NPO1099	Capparis spinosa	Species	Capparaceae	Eukaryota	Leaf	n.a.	n.a.	Database[FooDB]
NPO1099	Capparis spinosa	Species	Capparaceae	Eukaryota	Seed	n.a.	n.a.	Database[FooDB]
NPO1099	Capparis spinosa	Species	Capparaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO1099	Capparis spinosa	Species	Capparaceae	Eukaryota	n.a.	n.a.		Database[FooDB]
NPO1099	Capparis spinosa	Species	Capparaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO1099	Capparis spinosa	Species	Capparaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO1099	Capparis spinosa	Species	Capparaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]

☑ 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
EC50	2
IC50	2

Activity Type	# Activity
Organism	2
SINGLE PROTEIN	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT450	Organism	Meloidogyne incognita	Meloidogyne incognita	EC50	>	1000.0	ug.mL-1	PMID[520015]
NPT24039	SINGLE PROTEIN	E3 ubiquitin-protein ligase TRIM33	Homo sapiens	IC50	=	305.4	nM	PMID[520016]
NPT24040	SINGLE PROTEIN	Transcription intermediary factor 1-alpha	Homo sapiens	IC50	=	180.2	nM	PMID[520016]

☑ 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 NPC71236 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	1551
0.1-0.2	13520
0.2-0.3	18850
0.3-0.4	4235
0.4-0.5	2273
0.5-0.6	1695
0.6-0.7	490
0.7-0.8	76
0.8-0.85	2
0.85-0.9	2
0.9-0.95	1
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9457	High Similarity	NPC472288
0.9154	High Similarity	NPC23215
0.8984	High Similarity	NPC313823
0.8722	High Similarity	NPC291517
0.8138	Intermediate Similarity	NPC472260
0.8134	Intermediate Similarity	NPC471589
0.7857	Intermediate Similarity	NPC64661
0.7857	Intermediate Similarity	NPC98156
0.7857	Intermediate Similarity	NPC195704
0.7857	Intermediate Similarity	NPC200397
0.7857	Intermediate Similarity	NPC167200
0.7857	Intermediate Similarity	NPC14448
0.7857	Intermediate Similarity	NPC292434
0.7857	Intermediate Similarity	NPC138596
0.7815	Intermediate Similarity	NPC473706
0.7808	Intermediate Similarity	NPC100726
0.7667	Intermediate Similarity	NPC33229
0.7613	Intermediate Similarity	NPC114637
0.7586	Intermediate Similarity	NPC101130
0.7586	Intermediate Similarity	NPC114033
0.7586	Intermediate Similarity	NPC58268
0.7586	Intermediate Similarity	NPC129412
0.7584	Intermediate Similarity	NPC473878
0.7532	Intermediate Similarity	NPC242116
0.7517	Intermediate Similarity	NPC205604
0.7517	Intermediate Similarity	NPC97230
0.7517	Intermediate Similarity	NPC286529
0.7517	Intermediate Similarity	NPC12831
0.7517	Intermediate Similarity	NPC74928
0.7517	Intermediate Similarity	NPC59839
0.7517	Intermediate Similarity	NPC48171
0.7517	Intermediate Similarity	NPC302717
0.7517	Intermediate Similarity	NPC77582
0.7517	Intermediate Similarity	NPC129753
0.7517	Intermediate Similarity	NPC169308
0.7517	Intermediate Similarity	NPC3698
0.7517	Intermediate Similarity	NPC244087
0.7517	Intermediate Similarity	NPC209281
0.75	Intermediate Similarity	NPC302159
0.748	Intermediate Similarity	NPC231655
0.7432	Intermediate Similarity	NPC467188
0.7417	Intermediate Similarity	NPC470679
0.7417	Intermediate Similarity	NPC217021
0.7403	Intermediate Similarity	NPC80681
0.7358	Intermediate Similarity	NPC54214
0.7351	Intermediate Similarity	NPC471655
0.7325	Intermediate Similarity	NPC42372
0.732	Intermediate Similarity	NPC209362
0.7285	Intermediate Similarity	NPC102664
0.7273	Intermediate Similarity	NPC20021
0.7248	Intermediate Similarity	NPC230085
0.7248	Intermediate Similarity	NPC159630
0.7219	Intermediate Similarity	NPC105811
0.7215	Intermediate Similarity	NPC233380
0.7208	Intermediate Similarity	NPC474236
0.719	Intermediate Similarity	NPC70406
0.7171	Intermediate Similarity	NPC13432
0.716	Intermediate Similarity	NPC293216
0.7153	Intermediate Similarity	NPC330326
0.7143	Intermediate Similarity	NPC251391
0.7143	Intermediate Similarity	NPC83987
0.7126	Intermediate Similarity	NPC295158
0.7124	Intermediate Similarity	NPC313889
0.7108	Intermediate Similarity	NPC270834
0.7103	Intermediate Similarity	NPC150592
0.7097	Intermediate Similarity	NPC298288
0.7091	Intermediate Similarity	NPC314281
0.7091	Intermediate Similarity	NPC40530
0.7086	Intermediate Similarity	NPC260041
0.7078	Intermediate Similarity	NPC109158
0.7075	Intermediate Similarity	NPC65408
0.7055	Intermediate Similarity	NPC469529
0.7032	Intermediate Similarity	NPC312860
0.7025	Intermediate Similarity	NPC100104
0.7025	Intermediate Similarity	NPC470680
0.7019	Intermediate Similarity	NPC70949
0.7006	Intermediate Similarity	NPC27296
0.7006	Intermediate Similarity	NPC102755
0.7006	Intermediate Similarity	NPC213914
0.6993	Remote Similarity	NPC112741
0.6988	Remote Similarity	NPC73994
0.6987	Remote Similarity	NPC229055
0.6987	Remote Similarity	NPC263455
0.697	Remote Similarity	NPC83774
0.6959	Remote Similarity	NPC114310
0.6957	Remote Similarity	NPC41717
0.6948	Remote Similarity	NPC123906
0.6947	Remote Similarity	NPC76540
0.6946	Remote Similarity	NPC470677
0.6943	Remote Similarity	NPC74357
0.6937	Remote Similarity	NPC265100
0.6923	Remote Similarity	NPC107287
0.6905	Remote Similarity	NPC159125
0.6901	Remote Similarity	NPC209917
0.6886	Remote Similarity	NPC61011
0.6886	Remote Similarity	NPC477042
0.6863	Remote Similarity	NPC167400
0.6857	Remote Similarity	NPC182570
0.6857	Remote Similarity	NPC48564
0.6857	Remote Similarity	NPC265605
0.6855	Remote Similarity	NPC474492
0.6832	Remote Similarity	NPC306160
0.6832	Remote Similarity	NPC476418
0.6829	Remote Similarity	NPC273532
0.68	Remote Similarity	NPC104049
0.6791	Remote Similarity	NPC27802
0.6772	Remote Similarity	NPC75135
0.6766	Remote Similarity	NPC284775
0.6765	Remote Similarity	NPC110158
0.6765	Remote Similarity	NPC46895
0.6746	Remote Similarity	NPC191415
0.6735	Remote Similarity	NPC256893
0.673	Remote Similarity	NPC169586
0.6728	Remote Similarity	NPC206148
0.6725	Remote Similarity	NPC241025
0.6724	Remote Similarity	NPC210123
0.6721	Remote Similarity	NPC14223
0.6689	Remote Similarity	NPC322488
0.6687	Remote Similarity	NPC474383
0.6686	Remote Similarity	NPC476527
0.6667	Remote Similarity	NPC328029
0.6667	Remote Similarity	NPC477003
0.6648	Remote Similarity	NPC474767
0.6648	Remote Similarity	NPC477045
0.6646	Remote Similarity	NPC293487
0.6645	Remote Similarity	NPC85443
0.6642	Remote Similarity	NPC473901
0.6627	Remote Similarity	NPC226835
0.6627	Remote Similarity	NPC249614
0.6627	Remote Similarity	NPC253810
0.6627	Remote Similarity	NPC262338
0.6626	Remote Similarity	NPC478182
0.6623	Remote Similarity	NPC150259
0.6589	Remote Similarity	NPC213774
0.6588	Remote Similarity	NPC182940
0.6584	Remote Similarity	NPC76982
0.6571	Remote Similarity	NPC297486
0.6571	Remote Similarity	NPC471402
0.6571	Remote Similarity	NPC240136
0.657	Remote Similarity	NPC207851
0.6569	Remote Similarity	NPC235843
0.6568	Remote Similarity	NPC237188
0.6568	Remote Similarity	NPC157583
0.6564	Remote Similarity	NPC478185
0.6556	Remote Similarity	NPC81535
0.6548	Remote Similarity	NPC97106
0.6545	Remote Similarity	NPC56233
0.6532	Remote Similarity	NPC282103
0.6528	Remote Similarity	NPC46358
0.6527	Remote Similarity	NPC476421
0.6527	Remote Similarity	NPC227489
0.6527	Remote Similarity	NPC28096
0.6524	Remote Similarity	NPC274981
0.6522	Remote Similarity	NPC142688
0.6517	Remote Similarity	NPC93390
0.6516	Remote Similarity	NPC190296
0.651	Remote Similarity	NPC82295
0.6509	Remote Similarity	NPC476419
0.65	Remote Similarity	NPC477041
0.65	Remote Similarity	NPC477044
0.65	Remote Similarity	NPC281094
0.6494	Remote Similarity	NPC118084
0.6494	Remote Similarity	NPC238499
0.6491	Remote Similarity	NPC317010
0.6483	Remote Similarity	NPC27740
0.648	Remote Similarity	NPC77061
0.6479	Remote Similarity	NPC11863
0.6477	Remote Similarity	NPC268966
0.6471	Remote Similarity	NPC234987
0.6471	Remote Similarity	NPC84827
0.6471	Remote Similarity	NPC145885
0.6471	Remote Similarity	NPC14113
0.6463	Remote Similarity	NPC165370
0.645	Remote Similarity	NPC469938
0.6448	Remote Similarity	NPC106757
0.6448	Remote Similarity	NPC57398
0.6447	Remote Similarity	NPC29886
0.6447	Remote Similarity	NPC261195
0.6446	Remote Similarity	NPC478183
0.6444	Remote Similarity	NPC78767
0.6444	Remote Similarity	NPC473814
0.6442	Remote Similarity	NPC113812
0.6441	Remote Similarity	NPC476460
0.6433	Remote Similarity	NPC314372
0.6433	Remote Similarity	NPC285731
0.6429	Remote Similarity	NPC110126
0.6429	Remote Similarity	NPC84268
0.6429	Remote Similarity	NPC73767
0.6424	Remote Similarity	NPC478184
0.6412	Remote Similarity	NPC136441
0.6405	Remote Similarity	NPC84911
0.6395	Remote Similarity	NPC24864
0.6395	Remote Similarity	NPC79777
0.6391	Remote Similarity	NPC80528
0.6386	Remote Similarity	NPC115232
0.6386	Remote Similarity	NPC2414
0.6384	Remote Similarity	NPC154339
0.6378	Remote Similarity	NPC88115
0.6375	Remote Similarity	NPC52110
0.6374	Remote Similarity	NPC473380

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 NPC71236 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	341
0.1-0.2	1105
0.2-0.3	1388
0.3-0.4	2575
0.4-0.5	2375
0.5-0.6	1136
0.6-0.7	220
0.7-0.8	10
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
0.7868	Intermediate Similarity	NPD1031	Discontinued
0.7817	Intermediate Similarity	NPD569	Clinical (unspecified phase)
0.7662	Intermediate Similarity	NPD1568	Clinical (unspecified phase)
0.76	Intermediate Similarity	NPD180	Clinical (unspecified phase)
0.7535	Intermediate Similarity	NPD272	Approved
0.748	Intermediate Similarity	NPD9099	Clinical (unspecified phase)
0.748	Intermediate Similarity	NPD9098	Phase 3
0.7303	Intermediate Similarity	NPD9343	Clinical (unspecified phase)
0.72	Intermediate Similarity	NPD175	Clinical (unspecified phase)
0.7153	Intermediate Similarity	NPD9100	Approved
0.7075	Intermediate Similarity	NPD200	Phase 2
0.7075	Intermediate Similarity	NPD201	Phase 2
0.707	Intermediate Similarity	NPD1630	Approved
0.7047	Intermediate Similarity	NPD9599	Approved
0.7047	Intermediate Similarity	NPD107	Approved
0.7034	Intermediate Similarity	NPD1627	Clinical (unspecified phase)
0.6993	Remote Similarity	NPD9271	Approved
0.694	Remote Similarity	NPD4823	Approved
0.694	Remote Similarity	NPD4824	Approved
0.6937	Remote Similarity	NPD1631	Approved
0.6934	Remote Similarity	NPD9396	Approved
0.6934	Remote Similarity	NPD9392	Approved
0.6883	Remote Similarity	NPD1270	Approved
0.6867	Remote Similarity	NPD4804	Approved
0.6863	Remote Similarity	NPD9075	Approved
0.6863	Remote Similarity	NPD9074	Approved
0.686	Remote Similarity	NPD5685	Approved
0.686	Remote Similarity	NPD5686	Approved
0.6857	Remote Similarity	NPD9598	Discontinued
0.6857	Remote Similarity	NPD271	Approved
0.6857	Remote Similarity	NPD268	Approved
0.6857	Remote Similarity	NPD270	Clinical (unspecified phase)
0.6848	Remote Similarity	NPD4736	Clinical (unspecified phase)
0.6845	Remote Similarity	NPD3178	Discontinued
0.681	Remote Similarity	NPD1343	Approved
0.6792	Remote Similarity	NPD820	Phase 3
0.6781	Remote Similarity	NPD3475	Approved
0.6781	Remote Similarity	NPD3476	Approved
0.6779	Remote Similarity	NPD206	Clinical (unspecified phase)
0.6776	Remote Similarity	NPD4805	Approved
0.6768	Remote Similarity	NPD1573	Approved
0.6768	Remote Similarity	NPD1575	Approved
0.6746	Remote Similarity	NPD4011	Clinical (unspecified phase)
0.6746	Remote Similarity	NPD1783	Clinical (unspecified phase)
0.6707	Remote Similarity	NPD1292	Clinical (unspecified phase)
0.6686	Remote Similarity	NPD1291	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD1096	Discontinued
0.6667	Remote Similarity	NPD4436	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD3607	Clinical (unspecified phase)
0.6647	Remote Similarity	NPD1586	Approved
0.6646	Remote Similarity	NPD5965	Clinical (unspecified phase)
0.6646	Remote Similarity	NPD4174	Clinical (unspecified phase)
0.6597	Remote Similarity	NPD9357	Approved
0.6587	Remote Similarity	NPD750	Phase 2
0.6582	Remote Similarity	NPD7913	Clinical (unspecified phase)
0.6575	Remote Similarity	NPD2118	Approved
0.6575	Remote Similarity	NPD2119	Approved
0.6573	Remote Similarity	NPD2289	Phase 3
0.6573	Remote Similarity	NPD2290	Phase 3
0.6564	Remote Similarity	NPD5400	Approved
0.6552	Remote Similarity	NPD4988	Discontinued
0.6547	Remote Similarity	NPD60	Approved
0.6547	Remote Similarity	NPD269	Clinical (unspecified phase)
0.6541	Remote Similarity	NPD510	Phase 1
0.6536	Remote Similarity	NPD174	Discontinued
0.6529	Remote Similarity	NPD1587	Approved
0.6512	Remote Similarity	NPD7401	Clinical (unspecified phase)
0.6509	Remote Similarity	NPD3238	Discontinued
0.6507	Remote Similarity	NPD9583	Approved
0.65	Remote Similarity	NPD7459	Phase 2
0.6494	Remote Similarity	NPD4426	Clinical (unspecified phase)
0.6494	Remote Similarity	NPD5820	Clinical (unspecified phase)
0.6488	Remote Similarity	NPD4524	Discontinued
0.6484	Remote Similarity	NPD5017	Discontinued
0.6474	Remote Similarity	NPD751	Clinical (unspecified phase)
0.6471	Remote Similarity	NPD2753	Discontinued
0.6471	Remote Similarity	NPD9076	Clinical (unspecified phase)
0.6461	Remote Similarity	NPD460	Discontinued
0.6454	Remote Similarity	NPD8840	Approved
0.6452	Remote Similarity	NPD5020	Approved
0.6424	Remote Similarity	NPD4030	Approved
0.6424	Remote Similarity	NPD4029	Approved
0.6424	Remote Similarity	NPD4028	Approved
0.6419	Remote Similarity	NPD1095	Clinical (unspecified phase)
0.6402	Remote Similarity	NPD6454	Clinical (unspecified phase)
0.64	Remote Similarity	NPD803	Phase 1
0.6395	Remote Similarity	NPD3927	Phase 2
0.6395	Remote Similarity	NPD1643	Phase 3
0.6389	Remote Similarity	NPD4848	Phase 1
0.6387	Remote Similarity	NPD2222	Discontinued
0.6364	Remote Similarity	NPD2896	Discontinued
0.6358	Remote Similarity	NPD2061	Approved
0.6352	Remote Similarity	NPD1004	Phase 2
0.6352	Remote Similarity	NPD1005	Phase 2
0.6351	Remote Similarity	NPD991	Phase 2
0.6351	Remote Similarity	NPD9284	Approved
0.6351	Remote Similarity	NPD992	Clinical (unspecified phase)
0.6345	Remote Similarity	NPD748	Clinical (unspecified phase)
0.634	Remote Similarity	NPD198	Clinical (unspecified phase)
0.6333	Remote Similarity	NPD715	Phase 3
0.6323	Remote Similarity	NPD786	Approved
0.6319	Remote Similarity	NPD7204	Clinical (unspecified phase)
0.6316	Remote Similarity	NPD749	Clinical (unspecified phase)
0.6316	Remote Similarity	NPD3944	Approved
0.6316	Remote Similarity	NPD3942	Approved
0.6306	Remote Similarity	NPD3717	Discontinued
0.6294	Remote Similarity	NPD1037	Clinical (unspecified phase)
0.6291	Remote Similarity	NPD9726	Discontinued
0.629	Remote Similarity	NPD6288	Clinical (unspecified phase)
0.629	Remote Similarity	NPD3947	Discontinued
0.6286	Remote Similarity	NPD7564	Discontinued
0.6267	Remote Similarity	NPD3654	Approved
0.6267	Remote Similarity	NPD9305	Clinical (unspecified phase)
0.6264	Remote Similarity	NPD1952	Discontinued
0.6258	Remote Similarity	NPD203	Clinical (unspecified phase)
0.6258	Remote Similarity	NPD2809	Approved
0.6257	Remote Similarity	NPD6180	Clinical (unspecified phase)
0.6257	Remote Similarity	NPD1658	Discontinued
0.6257	Remote Similarity	NPD482	Approved
0.625	Remote Similarity	NPD4547	Phase 3
0.6243	Remote Similarity	NPD8304	Clinical (unspecified phase)
0.6243	Remote Similarity	NPD1600	Suspended
0.6243	Remote Similarity	NPD3432	Approved
0.6243	Remote Similarity	NPD7704	Clinical (unspecified phase)
0.6242	Remote Similarity	NPD9080	Approved
0.6228	Remote Similarity	NPD8129	Discovery
0.6222	Remote Similarity	NPD7098	Clinical (unspecified phase)
0.6213	Remote Similarity	NPD4640	Approved
0.6213	Remote Similarity	NPD4639	Approved
0.6213	Remote Similarity	NPD4638	Approved
0.6205	Remote Similarity	NPD2511	Approved
0.6203	Remote Similarity	NPD2006	Phase 2
0.6201	Remote Similarity	NPD1905	Clinical (unspecified phase)
0.619	Remote Similarity	NPD2915	Discontinued
0.6188	Remote Similarity	NPD7469	Discontinued
0.6178	Remote Similarity	NPD1395	Clinical (unspecified phase)
0.6168	Remote Similarity	NPD6771	Discontinued
0.6164	Remote Similarity	NPD649	Clinical (unspecified phase)
0.6163	Remote Similarity	NPD4883	Approved
0.6162	Remote Similarity	NPD8248	Clinical (unspecified phase)
0.6154	Remote Similarity	NPD4643	Clinical (unspecified phase)
0.6154	Remote Similarity	NPD7944	Discontinued
0.6154	Remote Similarity	NPD1380	Discovery
0.6154	Remote Similarity	NPD6446	Discontinued
0.6154	Remote Similarity	NPD1623	Approved
0.6149	Remote Similarity	NPD4703	Approved
0.6149	Remote Similarity	NPD4702	Approved
0.6145	Remote Similarity	NPD704	Clinical (unspecified phase)
0.614	Remote Similarity	NPD754	Clinical (unspecified phase)
0.6139	Remote Similarity	NPD1722	Approved
0.6133	Remote Similarity	NPD981	Phase 2
0.6131	Remote Similarity	NPD3583	Phase 2
0.6131	Remote Similarity	NPD1545	Discontinued
0.6131	Remote Similarity	NPD5088	Discontinued
0.6127	Remote Similarity	NPD4385	Clinical (unspecified phase)
0.6124	Remote Similarity	NPD5809	Phase 3
0.6121	Remote Similarity	NPD276	Clinical (unspecified phase)
0.612	Remote Similarity	NPD1851	Clinical (unspecified phase)
0.6118	Remote Similarity	NPD9207	Approved
0.6118	Remote Similarity	NPD9206	Approved
0.6117	Remote Similarity	NPD6987	Phase 1
0.6115	Remote Similarity	NPD2071	Approved
0.6115	Remote Similarity	NPD2073	Approved
0.6115	Remote Similarity	NPD2075	Approved
0.6115	Remote Similarity	NPD2074	Approved
0.6115	Remote Similarity	NPD2068	Approved
0.6115	Remote Similarity	NPD2070	Approved
0.6115	Remote Similarity	NPD2072	Approved
0.6115	Remote Similarity	NPD2069	Approved
0.6114	Remote Similarity	NPD1618	Phase 2
0.6111	Remote Similarity	NPD3100	Discontinued
0.6108	Remote Similarity	NPD6137	Clinical (unspecified phase)
0.6104	Remote Similarity	NPD3385	Approved
0.6096	Remote Similarity	NPD2879	Approved
0.6096	Remote Similarity	NPD2881	Approved
0.6092	Remote Similarity	NPD5755	Clinical (unspecified phase)
0.609	Remote Similarity	NPD9506	Approved
0.6085	Remote Similarity	NPD7289	Clinical (unspecified phase)
0.6085	Remote Similarity	NPD2008	Discontinued
0.6084	Remote Similarity	NPD2582	Approved
0.6084	Remote Similarity	NPD2581	Approved
0.6084	Remote Similarity	NPD4326	Phase 2
0.6078	Remote Similarity	NPD809	Discontinued
0.6067	Remote Similarity	NPD5555	Phase 1
0.6067	Remote Similarity	NPD1308	Approved
0.6064	Remote Similarity	NPD2121	Clinical (unspecified phase)
0.6053	Remote Similarity	NPD1506	Discontinued
0.6053	Remote Similarity	NPD3839	Phase 2
0.6053	Remote Similarity	NPD3840	Phase 2
0.6049	Remote Similarity	NPD2089	Clinical (unspecified phase)
0.6045	Remote Similarity	NPD2095	Phase 2
0.6045	Remote Similarity	NPD2094	Phase 2
0.6045	Remote Similarity	NPD2092	Phase 2
0.6038	Remote Similarity	NPD1383	Phase 3
0.6038	Remote Similarity	NPD1382	Phase 2
0.6034	Remote Similarity	NPD4075	Phase 2
0.6034	Remote Similarity	NPD5104	Approved
0.6034	Remote Similarity	NPD6471	Clinical (unspecified phase)
0.6032	Remote Similarity	NPD3247	Clinical (unspecified phase)
0.6031	Remote Similarity	NPD6787	Phase 2

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