NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	111.03
Volume:	107.148
LogP:	0.87
LogD:	-0.272
LogS:	-1.571
# Rotatable Bonds:	1
TPSA:	53.09
# H-Bond Aceptor:	3
# H-Bond Donor:	2
# Rings:	1
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.56
Synthetic Accessibility Score:	2.65
Fsp3:	0.0
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.16
MDCK Permeability:	5.045594207331305e-06
Pgp-inhibitor:	0.001
Pgp-substrate:	0.008
Human Intestinal Absorption (HIA):	0.016
20% Bioavailability (F20%):	0.002
30% Bioavailability (F30%):	0.604

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.721
Plasma Protein Binding (PPB):	11.409003257751465%
Volume Distribution (VD):	0.286
Pgp-substrate:	82.92384338378906%

ADMET: Metabolism

CYP1A2-inhibitor:	0.031
CYP1A2-substrate:	0.232
CYP2C19-inhibitor:	0.059
CYP2C19-substrate:	0.051
CYP2C9-inhibitor:	0.024
CYP2C9-substrate:	0.188
CYP2D6-inhibitor:	0.03
CYP2D6-substrate:	0.094
CYP3A4-inhibitor:	0.029
CYP3A4-substrate:	0.089

ADMET: Excretion

Clearance (CL):	4.838
Half-life (T1/2):	0.939

ADMET: Toxicity

hERG Blockers:	0.073
Human Hepatotoxicity (H-HT):	0.259
Drug-inuced Liver Injury (DILI):	0.845
AMES Toxicity:	0.014
Rat Oral Acute Toxicity:	0.532
Maximum Recommended Daily Dose:	0.012
Skin Sensitization:	0.444
Carcinogencity:	0.038
Eye Corrosion:	0.043
Eye Irritation:	0.993
Respiratory Toxicity:	0.105

Download Data

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

Natural Product: NPC194541

Natural Product ID:	NPC194541
*Common Name:**	1H-Pyrrole-3-Carboxylic Acid
IUPAC Name:	1H-pyrrole-3-carboxylic acid
Synonyms:
Standard InCHIKey:	DOYOPBSXEIZLRE-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C5H5NO2/c7-5(8)4-1-2-6-3-4/h1-3,6H,(H,7,8)
SMILES:	OC(=O)c1c[nH]cc1
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL79155
PubChem CID:	101030
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000090] Pyrroles [CHEMONTID:0002554] Pyrrole carboxylic acids and derivatives [CHEMONTID:0002555] Pyrrole carboxylic 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
NPO16076	Penicillium chrysogenum	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[1367520]
NPO16076	Penicillium chrysogenum	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15974609]
NPO16076	Penicillium chrysogenum	Species	Aspergillaceae	Eukaryota	n.a.	mycelium	n.a.	PMID[21381678]
NPO16076	Penicillium chrysogenum	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21667925]
NPO16076	Penicillium chrysogenum	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22118684]
NPO16076	Penicillium chrysogenum	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26692349]
NPO16076	Penicillium chrysogenum	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[33089690]
NPO16076	Penicillium chrysogenum	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[8626236]
NPO16076	Penicillium chrysogenum	Species	Aspergillaceae	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
Others	2

Activity Type	# Activity
Others	1
SINGLE PROTEIN	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT2	Others	Unspecified		Inhibition	=	46.0	%	PMID[515540]
NPT26851	SINGLE PROTEIN	Palmitoleoyl-protein carboxylesterase NOTUM	Homo sapiens	IC50	>	100000.0	nM	PMID[515541]
NPT26851	SINGLE PROTEIN	Palmitoleoyl-protein carboxylesterase NOTUM	Homo sapiens	Inhibition	<	20.0	%	PMID[515541]

☑ 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 NPC194541 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	1079
0.1-0.2	11541
0.2-0.3	22273
0.3-0.4	3916
0.4-0.5	2583
0.5-0.6	1191
0.6-0.7	108
0.7-0.8	5
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
0.7639	Intermediate Similarity	NPC114310
0.753	Intermediate Similarity	NPC278434
0.7517	Intermediate Similarity	NPC167400
0.7516	Intermediate Similarity	NPC33229
0.7105	Intermediate Similarity	NPC159630
0.7105	Intermediate Similarity	NPC230085
0.7044	Intermediate Similarity	NPC113812
0.7006	Intermediate Similarity	NPC312860
0.6994	Remote Similarity	NPC138370
0.6988	Remote Similarity	NPC476419
0.6968	Remote Similarity	NPC112741
0.6962	Remote Similarity	NPC263455
0.696	Remote Similarity	NPC196580
0.6846	Remote Similarity	NPC62151
0.6839	Remote Similarity	NPC83111
0.6792	Remote Similarity	NPC107287
0.6779	Remote Similarity	NPC314646
0.6765	Remote Similarity	NPC317010
0.6707	Remote Similarity	NPC273532
0.6707	Remote Similarity	NPC302647
0.6667	Remote Similarity	NPC322488
0.6645	Remote Similarity	NPC29702
0.6609	Remote Similarity	NPC311282
0.6592	Remote Similarity	NPC202812
0.6582	Remote Similarity	NPC302159
0.6579	Remote Similarity	NPC23215
0.6579	Remote Similarity	NPC291517
0.6554	Remote Similarity	NPC154339
0.6554	Remote Similarity	NPC306397
0.6533	Remote Similarity	NPC327941
0.6505	Remote Similarity	NPC82053
0.6485	Remote Similarity	NPC131718
0.6471	Remote Similarity	NPC183777
0.6467	Remote Similarity	NPC42372
0.6467	Remote Similarity	NPC233380
0.6453	Remote Similarity	NPC111275
0.6444	Remote Similarity	NPC267343
0.6443	Remote Similarity	NPC74360
0.6436	Remote Similarity	NPC171787
0.6429	Remote Similarity	NPC41717
0.642	Remote Similarity	NPC282103
0.6407	Remote Similarity	NPC102423
0.64	Remote Similarity	NPC471589
0.6392	Remote Similarity	NPC141385
0.6364	Remote Similarity	NPC212742
0.6333	Remote Similarity	NPC212125
0.6333	Remote Similarity	NPC165370
0.6302	Remote Similarity	NPC219087
0.6265	Remote Similarity	NPC213914
0.6243	Remote Similarity	NPC293216
0.6242	Remote Similarity	NPC75135
0.6237	Remote Similarity	NPC213308
0.6235	Remote Similarity	NPC105811
0.6234	Remote Similarity	NPC330326
0.6229	Remote Similarity	NPC164340
0.6222	Remote Similarity	NPC209917
0.6216	Remote Similarity	NPC474916
0.6213	Remote Similarity	NPC162268
0.6205	Remote Similarity	NPC169586
0.6203	Remote Similarity	NPC471944
0.6199	Remote Similarity	NPC78020
0.6196	Remote Similarity	NPC77061
0.6196	Remote Similarity	NPC13432
0.6185	Remote Similarity	NPC313791
0.6175	Remote Similarity	NPC473821
0.6172	Remote Similarity	NPC14223
0.6162	Remote Similarity	NPC156704
0.6162	Remote Similarity	NPC74153
0.6159	Remote Similarity	NPC52110
0.6158	Remote Similarity	NPC71037
0.615	Remote Similarity	NPC229893
0.6145	Remote Similarity	NPC209362
0.6145	Remote Similarity	NPC280290
0.6136	Remote Similarity	NPC55772
0.6127	Remote Similarity	NPC249614
0.6115	Remote Similarity	NPC328029
0.6111	Remote Similarity	NPC467188
0.6111	Remote Similarity	NPC159856
0.6094	Remote Similarity	NPC266249
0.6089	Remote Similarity	NPC207851
0.6089	Remote Similarity	NPC477003
0.6082	Remote Similarity	NPC41333
0.6082	Remote Similarity	NPC82370
0.608	Remote Similarity	NPC276657
0.608	Remote Similarity	NPC284775
0.6075	Remote Similarity	NPC90229
0.6067	Remote Similarity	NPC470677
0.6064	Remote Similarity	NPC45459
0.6064	Remote Similarity	NPC315491
0.6057	Remote Similarity	NPC149155
0.6057	Remote Similarity	NPC203468
0.6057	Remote Similarity	NPC110500
0.6056	Remote Similarity	NPC295158
0.6048	Remote Similarity	NPC229055
0.6043	Remote Similarity	NPC131887
0.6036	Remote Similarity	NPC474492
0.6031	Remote Similarity	NPC123839
0.6027	Remote Similarity	NPC291389
0.6023	Remote Similarity	NPC267885
0.6022	Remote Similarity	NPC315555
0.6012	Remote Similarity	NPC74357
0.6	Remote Similarity	NPC110158
0.5989	Remote Similarity	NPC96890
0.5989	Remote Similarity	NPC184964
0.5988	Remote Similarity	NPC251391
0.5976	Remote Similarity	NPC138018
0.5975	Remote Similarity	NPC472288
0.5964	Remote Similarity	NPC105818
0.5964	Remote Similarity	NPC471655
0.5964	Remote Similarity	NPC24678
0.5957	Remote Similarity	NPC67288
0.5956	Remote Similarity	NPC44354
0.5955	Remote Similarity	NPC283219
0.5955	Remote Similarity	NPC126709
0.5955	Remote Similarity	NPC248041
0.5955	Remote Similarity	NPC213468
0.5949	Remote Similarity	NPC309845
0.5944	Remote Similarity	NPC469358
0.5943	Remote Similarity	NPC253810
0.5941	Remote Similarity	NPC230869
0.5936	Remote Similarity	NPC109922
0.5935	Remote Similarity	NPC71236
0.5933	Remote Similarity	NPC15566
0.593	Remote Similarity	NPC27041
0.593	Remote Similarity	NPC472285
0.5928	Remote Similarity	NPC70406
0.5926	Remote Similarity	NPC103361
0.5915	Remote Similarity	NPC314372
0.5906	Remote Similarity	NPC470680
0.5906	Remote Similarity	NPC100104
0.5904	Remote Similarity	NPC78767
0.5904	Remote Similarity	NPC473814
0.5902	Remote Similarity	NPC46580
0.5892	Remote Similarity	NPC114974
0.5892	Remote Similarity	NPC476460
0.589	Remote Similarity	NPC190296
0.5882	Remote Similarity	NPC151489
0.5882	Remote Similarity	NPC135950
0.5882	Remote Similarity	NPC93390
0.5879	Remote Similarity	NPC314002
0.5876	Remote Similarity	NPC88008
0.5873	Remote Similarity	NPC317672
0.5872	Remote Similarity	NPC242116
0.587	Remote Similarity	NPC221873
0.5868	Remote Similarity	NPC313889
0.5866	Remote Similarity	NPC276540
0.5866	Remote Similarity	NPC233050
0.5856	Remote Similarity	NPC220765
0.5847	Remote Similarity	NPC62749
0.5833	Remote Similarity	NPC109158
0.5824	Remote Similarity	NPC204717
0.581	Remote Similarity	NPC219848
0.581	Remote Similarity	NPC182222
0.5808	Remote Similarity	NPC110182
0.5808	Remote Similarity	NPC123906
0.5805	Remote Similarity	NPC474383
0.5803	Remote Similarity	NPC98715
0.5802	Remote Similarity	NPC85443
0.5801	Remote Similarity	NPC191415
0.5801	Remote Similarity	NPC275292
0.5801	Remote Similarity	NPC243381
0.5799	Remote Similarity	NPC259644
0.5799	Remote Similarity	NPC469760
0.5799	Remote Similarity	NPC469765
0.5799	Remote Similarity	NPC73952
0.5799	Remote Similarity	NPC469763
0.5799	Remote Similarity	NPC25008
0.5799	Remote Similarity	NPC469786
0.5798	Remote Similarity	NPC146724
0.5796	Remote Similarity	NPC315320
0.5789	Remote Similarity	NPC469762
0.5789	Remote Similarity	NPC207686
0.5789	Remote Similarity	NPC27296
0.5778	Remote Similarity	NPC256268
0.5778	Remote Similarity	NPC42979
0.5771	Remote Similarity	NPC114637
0.5769	Remote Similarity	NPC102755
0.5769	Remote Similarity	NPC48938
0.5765	Remote Similarity	NPC70922
0.5765	Remote Similarity	NPC211572
0.5765	Remote Similarity	NPC75540
0.5765	Remote Similarity	NPC80597
0.5765	Remote Similarity	NPC212376
0.5761	Remote Similarity	NPC171171
0.5761	Remote Similarity	NPC235684
0.5759	Remote Similarity	NPC293917
0.5759	Remote Similarity	NPC82295
0.5759	Remote Similarity	NPC174421
0.5758	Remote Similarity	NPC471323
0.5756	Remote Similarity	NPC92796
0.5756	Remote Similarity	NPC135141
0.5754	Remote Similarity	NPC224764
0.5753	Remote Similarity	NPC469489
0.5751	Remote Similarity	NPC57398
0.5747	Remote Similarity	NPC274981
0.5747	Remote Similarity	NPC311276
0.5746	Remote Similarity	NPC477042
0.5745	Remote Similarity	NPC304203
0.5745	Remote Similarity	NPC326422
0.5745	Remote Similarity	NPC88315

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 NPC194541 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	268
0.1-0.2	1026
0.2-0.3	2177
0.3-0.4	2987
0.4-0.5	2173
0.5-0.6	493
0.6-0.7	24
0.7-0.8	2
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
0.7517	Intermediate Similarity	NPD9074	Approved
0.7517	Intermediate Similarity	NPD9075	Approved
0.7248	Intermediate Similarity	NPD107	Approved
0.7024	Intermediate Similarity	NPD3178	Discontinued
0.7	Intermediate Similarity	NPD203	Clinical (unspecified phase)
0.6968	Remote Similarity	NPD9271	Approved
0.6667	Remote Similarity	NPD820	Phase 3
0.6576	Remote Similarity	NPD2121	Clinical (unspecified phase)
0.6554	Remote Similarity	NPD9080	Approved
0.6444	Remote Similarity	NPD1173	Approved
0.6437	Remote Similarity	NPD1783	Clinical (unspecified phase)
0.6436	Remote Similarity	NPD2509	Approved
0.6436	Remote Similarity	NPD2510	Approved
0.6402	Remote Similarity	NPD276	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD5901	Discontinued
0.6333	Remote Similarity	NPD9284	Approved
0.6271	Remote Similarity	NPD1096	Discontinued
0.6243	Remote Similarity	NPD4559	Clinical (unspecified phase)
0.6242	Remote Similarity	NPD2061	Approved
0.6234	Remote Similarity	NPD9100	Approved
0.6205	Remote Similarity	NPD3393	Approved
0.6205	Remote Similarity	NPD3389	Approved
0.6205	Remote Similarity	NPD3394	Approved
0.6164	Remote Similarity	NPD9599	Approved
0.6154	Remote Similarity	NPD272	Approved
0.6136	Remote Similarity	NPD8304	Clinical (unspecified phase)
0.6105	Remote Similarity	NPD944	Approved
0.6076	Remote Similarity	NPD9506	Approved
0.6064	Remote Similarity	NPD484	Approved
0.6064	Remote Similarity	NPD8248	Clinical (unspecified phase)
0.6057	Remote Similarity	NPD482	Approved
0.6054	Remote Similarity	NPD5975	Clinical (unspecified phase)
0.6051	Remote Similarity	NPD3916	Clinical (unspecified phase)
0.6051	Remote Similarity	NPD3918	Approved
0.6051	Remote Similarity	NPD3917	Approved
0.6034	Remote Similarity	NPD485	Clinical (unspecified phase)
0.6033	Remote Similarity	NPD6665	Discontinued
0.6024	Remote Similarity	NPD510	Phase 1
0.6023	Remote Similarity	NPD749	Clinical (unspecified phase)
0.6021	Remote Similarity	NPD3947	Discontinued
0.6011	Remote Similarity	NPD1618	Phase 2
0.6	Remote Similarity	NPD3915	Approved
0.6	Remote Similarity	NPD569	Clinical (unspecified phase)
0.6	Remote Similarity	NPD2096	Phase 2
0.6	Remote Similarity	NPD2091	Phase 2
0.5989	Remote Similarity	NPD4948	Discontinued
0.5977	Remote Similarity	NPD1573	Approved
0.5977	Remote Similarity	NPD1575	Approved
0.5966	Remote Similarity	NPD5065	Approved
0.5963	Remote Similarity	NPD1649	Discontinued
0.5944	Remote Similarity	NPD2094	Phase 2
0.5944	Remote Similarity	NPD2095	Phase 2
0.5944	Remote Similarity	NPD2092	Phase 2
0.5941	Remote Similarity	NPD704	Clinical (unspecified phase)
0.5938	Remote Similarity	NPD2896	Discontinued
0.593	Remote Similarity	NPD5088	Discontinued
0.5928	Remote Similarity	NPD5965	Clinical (unspecified phase)
0.5915	Remote Similarity	NPD175	Clinical (unspecified phase)
0.5892	Remote Similarity	NPD5592	Clinical (unspecified phase)
0.586	Remote Similarity	NPD4376	Phase 3
0.586	Remote Similarity	NPD981	Phase 2
0.5856	Remote Similarity	NPD5728	Clinical (unspecified phase)
0.5855	Remote Similarity	NPD7396	Approved
0.5854	Remote Similarity	NPD1352	Discontinued
0.5843	Remote Similarity	NPD1270	Approved
0.5842	Remote Similarity	NPD6137	Clinical (unspecified phase)
0.5838	Remote Similarity	NPD1631	Approved
0.5838	Remote Similarity	NPD5475	Discontinued
0.5829	Remote Similarity	NPD460	Discontinued
0.58	Remote Similarity	NPD5490	Discontinued
0.5796	Remote Similarity	NPD9206	Approved
0.5796	Remote Similarity	NPD9207	Approved
0.5787	Remote Similarity	NPD4883	Approved
0.5779	Remote Similarity	NPD3794	Approved
0.5779	Remote Similarity	NPD3795	Approved
0.5764	Remote Similarity	NPD245	Suspended
0.5759	Remote Similarity	NPD7621	Clinical (unspecified phase)
0.5758	Remote Similarity	NPD3813	Approved
0.5746	Remote Similarity	NPD1643	Phase 3
0.5746	Remote Similarity	NPD1291	Clinical (unspecified phase)
0.5743	Remote Similarity	NPD269	Clinical (unspecified phase)
0.5742	Remote Similarity	NPD9081	Clinical (unspecified phase)
0.573	Remote Similarity	NPD750	Phase 2
0.5729	Remote Similarity	NPD8096	Phase 3
0.5729	Remote Similarity	NPD8097	Phase 3
0.5728	Remote Similarity	NPD7269	Clinical (unspecified phase)
0.5714	Remote Similarity	NPD1568	Clinical (unspecified phase)
0.5714	Remote Similarity	NPD3371	Approved
0.5714	Remote Similarity	NPD6838	Clinical (unspecified phase)
0.5698	Remote Similarity	NPD5322	Clinical (unspecified phase)
0.5692	Remote Similarity	NPD6987	Phase 1
0.5676	Remote Similarity	NPD706	Phase 1
0.5665	Remote Similarity	NPD1630	Approved
0.5663	Remote Similarity	NPD4862	Clinical (unspecified phase)
0.5657	Remote Similarity	NPD5140	Approved
0.5657	Remote Similarity	NPD5138	Approved
0.5652	Remote Similarity	NPD3607	Clinical (unspecified phase)
0.5652	Remote Similarity	NPD3569	Discontinued
0.565	Remote Similarity	NPD5069	Clinical (unspecified phase)
0.565	Remote Similarity	NPD2844	Phase 3
0.565	Remote Similarity	NPD8093	Discontinued
0.5638	Remote Similarity	NPD2336	Approved
0.5638	Remote Similarity	NPD6180	Clinical (unspecified phase)
0.5636	Remote Similarity	NPD1592	Phase 3
0.5636	Remote Similarity	NPD5020	Approved
0.5628	Remote Similarity	NPD7998	Clinical (unspecified phase)
0.5625	Remote Similarity	NPD1627	Clinical (unspecified phase)
0.5622	Remote Similarity	NPD8094	Discontinued
0.5617	Remote Similarity	NPD198	Clinical (unspecified phase)
0.5614	Remote Similarity	NPD180	Clinical (unspecified phase)
0.561	Remote Similarity	NPD3280	Approved
0.5608	Remote Similarity	NPD2127	Suspended
0.5604	Remote Similarity	NPD6173	Approved
0.56	Remote Similarity	NPD7470	Discontinued

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