NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	191.06
Volume:	188.589
LogP:	2.294
LogD:	2.221
LogS:	-2.966
# Rotatable Bonds:	2
TPSA:	62.32
# H-Bond Aceptor:	4
# H-Bond Donor:	2
# Rings:	2
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.761
Synthetic Accessibility Score:	1.887
Fsp3:	0.1
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	2
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.846
MDCK Permeability:	6.0125134950794745e-06
Pgp-inhibitor:	0.0
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.007
20% Bioavailability (F20%):	0.002
30% Bioavailability (F30%):	0.776

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.595
Plasma Protein Binding (PPB):	64.61670684814453%
Volume Distribution (VD):	0.571
Pgp-substrate:	26.67962074279785%

ADMET: Metabolism

CYP1A2-inhibitor:	0.25
CYP1A2-substrate:	0.814
CYP2C19-inhibitor:	0.066
CYP2C19-substrate:	0.055
CYP2C9-inhibitor:	0.032
CYP2C9-substrate:	0.343
CYP2D6-inhibitor:	0.014
CYP2D6-substrate:	0.178
CYP3A4-inhibitor:	0.025
CYP3A4-substrate:	0.082

ADMET: Excretion

Clearance (CL):	4.832
Half-life (T1/2):	0.877

ADMET: Toxicity

hERG Blockers:	0.035
Human Hepatotoxicity (H-HT):	0.544
Drug-inuced Liver Injury (DILI):	0.968
AMES Toxicity:	0.013
Rat Oral Acute Toxicity:	0.865
Maximum Recommended Daily Dose:	0.161
Skin Sensitization:	0.095
Carcinogencity:	0.089
Eye Corrosion:	0.014
Eye Irritation:	0.979
Respiratory Toxicity:	0.912

Download Data

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

Natural Product: NPC321428

Natural Product ID:	NPC321428
*Common Name:**	5-Methoxy-1H-Indole-2-Carboxylic Acid
IUPAC Name:	5-methoxy-1H-indole-2-carboxylic acid
Synonyms:
Standard InCHIKey:	YEBJVSLNUMZXRJ-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C10H9NO3/c1-14-7-2-3-8-6(4-7)5-9(11-8)10(12)13/h2-5,11H,1H3,(H,12,13)
SMILES:	COC1=CC2=C(C=C1)NC(=C2)C(=O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL23961
PubChem CID:	20401
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000211] Indoles and derivatives [CHEMONTID:0002013] Indolecarboxylic acids and derivatives

*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
NPO21080	Solanum lycopersicum	Species	Solanaceae	Eukaryota	n.a.	fruit	n.a.	DOI[10.1007/s11306-014-0728-9]
NPO21080	Solanum lycopersicum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1038/sdata.2014.29]
NPO21080	Solanum lycopersicum	Species	Solanaceae	Eukaryota	n.a.	fruit	n.a.	PMID[11171227]
NPO21080	Solanum lycopersicum	Species	Solanaceae	Eukaryota	n.a.	fruit	n.a.	PMID[12576668]
NPO21080	Solanum lycopersicum	Species	Solanaceae	Eukaryota	n.a.	seed	n.a.	PMID[25891114]
NPO21080	Solanum lycopersicum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[8987503]
NPO21080	Solanum lycopersicum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[MetaboLights]
NPO21080	Solanum lycopersicum	Species	Solanaceae	Eukaryota	n.a.	fruit	n.a.	Database[MetaboLights]
NPO21080	Solanum lycopersicum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO21080	Solanum lycopersicum	Species	Solanaceae	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
Kd	1
Ki	1

Activity Type	# Activity
Individual Protein	1
Protein Complex	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT5224	Individual Protein	NS3	Hepatitis C virus	Kd	~	4000.0	nM	PMID[470260]
NPT1496	Protein Complex	Glutamate NMDA receptor	Rattus norvegicus	Ki	>	100000.0	nM	PMID[470259]

☑ 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 NPC321428 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	387
0.1-0.2	3401
0.2-0.3	12694
0.3-0.4	4041
0.4-0.5	16395
0.5-0.6	3477
0.6-0.7	1761
0.7-0.8	489
0.8-0.85	44
0.85-0.9	7
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.901	High Similarity	NPC300156
0.8894	High Similarity	NPC184408
0.8718	High Similarity	NPC45190
0.8693	High Similarity	NPC39500
0.8687	High Similarity	NPC87413
0.868	High Similarity	NPC325297
0.865	High Similarity	NPC118228
0.8485	Intermediate Similarity	NPC4687
0.8442	Intermediate Similarity	NPC39679
0.8426	Intermediate Similarity	NPC476098
0.8421	Intermediate Similarity	NPC274640
0.8408	Intermediate Similarity	NPC187501
0.8398	Intermediate Similarity	NPC280799
0.8365	Intermediate Similarity	NPC179287
0.8357	Intermediate Similarity	NPC144452
0.835	Intermediate Similarity	NPC174760
0.8342	Intermediate Similarity	NPC230403
0.8318	Intermediate Similarity	NPC15801
0.8317	Intermediate Similarity	NPC51388
0.8317	Intermediate Similarity	NPC294375
0.83	Intermediate Similarity	NPC270918
0.8299	Intermediate Similarity	NPC276517
0.8252	Intermediate Similarity	NPC46561
0.8235	Intermediate Similarity	NPC89508
0.8214	Intermediate Similarity	NPC141454
0.8213	Intermediate Similarity	NPC208084
0.8213	Intermediate Similarity	NPC74360
0.8209	Intermediate Similarity	NPC249583
0.8195	Intermediate Similarity	NPC116238
0.8182	Intermediate Similarity	NPC213308
0.8164	Intermediate Similarity	NPC247803
0.8155	Intermediate Similarity	NPC3207
0.815	Intermediate Similarity	NPC165599
0.8137	Intermediate Similarity	NPC9894
0.8125	Intermediate Similarity	NPC160381
0.8119	Intermediate Similarity	NPC283117
0.8116	Intermediate Similarity	NPC169402
0.8116	Intermediate Similarity	NPC312645
0.8109	Intermediate Similarity	NPC132539
0.809	Intermediate Similarity	NPC315491
0.809	Intermediate Similarity	NPC45459
0.8086	Intermediate Similarity	NPC225279
0.8086	Intermediate Similarity	NPC150239
0.8084	Intermediate Similarity	NPC474688
0.8084	Intermediate Similarity	NPC474701
0.8075	Intermediate Similarity	NPC194740
0.8063	Intermediate Similarity	NPC176127
0.804	Intermediate Similarity	NPC280714
0.8037	Intermediate Similarity	NPC475844
0.803	Intermediate Similarity	NPC244741
0.8028	Intermediate Similarity	NPC478078
0.801	Intermediate Similarity	NPC308137
0.801	Intermediate Similarity	NPC310211
0.7991	Intermediate Similarity	NPC473800
0.799	Intermediate Similarity	NPC96321
0.799	Intermediate Similarity	NPC306376
0.7982	Intermediate Similarity	NPC6786
0.798	Intermediate Similarity	NPC251090
0.7952	Intermediate Similarity	NPC288987
0.795	Intermediate Similarity	NPC128823
0.7941	Intermediate Similarity	NPC193238
0.7917	Intermediate Similarity	NPC260434
0.7915	Intermediate Similarity	NPC472099
0.7879	Intermediate Similarity	NPC307963
0.7874	Intermediate Similarity	NPC146418
0.7867	Intermediate Similarity	NPC165964
0.7857	Intermediate Similarity	NPC293151
0.7854	Intermediate Similarity	NPC88008
0.7846	Intermediate Similarity	NPC194040
0.7837	Intermediate Similarity	NPC219087
0.7833	Intermediate Similarity	NPC199277
0.7833	Intermediate Similarity	NPC135887
0.7826	Intermediate Similarity	NPC471304
0.782	Intermediate Similarity	NPC303658
0.7817	Intermediate Similarity	NPC144381
0.7816	Intermediate Similarity	NPC171787
0.781	Intermediate Similarity	NPC148183
0.781	Intermediate Similarity	NPC469928
0.781	Intermediate Similarity	NPC152768
0.7808	Intermediate Similarity	NPC39370
0.7798	Intermediate Similarity	NPC473186
0.7798	Intermediate Similarity	NPC474192
0.7798	Intermediate Similarity	NPC475720
0.7794	Intermediate Similarity	NPC223427
0.7794	Intermediate Similarity	NPC134848
0.7793	Intermediate Similarity	NPC60621
0.7778	Intermediate Similarity	NPC157931
0.7766	Intermediate Similarity	NPC296527
0.7766	Intermediate Similarity	NPC242928
0.7751	Intermediate Similarity	NPC118940
0.775	Intermediate Similarity	NPC131017
0.7742	Intermediate Similarity	NPC322644
0.7742	Intermediate Similarity	NPC311906
0.7736	Intermediate Similarity	NPC174576
0.7729	Intermediate Similarity	NPC210828
0.7729	Intermediate Similarity	NPC86834
0.7727	Intermediate Similarity	NPC76748
0.772	Intermediate Similarity	NPC88363
0.7718	Intermediate Similarity	NPC472287
0.7718	Intermediate Similarity	NPC472286
0.771	Intermediate Similarity	NPC198503
0.7704	Intermediate Similarity	NPC241025
0.7703	Intermediate Similarity	NPC23294
0.77	Intermediate Similarity	NPC475190
0.7688	Intermediate Similarity	NPC92111
0.7681	Intermediate Similarity	NPC193777
0.7677	Intermediate Similarity	NPC221873
0.7673	Intermediate Similarity	NPC156704
0.7668	Intermediate Similarity	NPC475816
0.7664	Intermediate Similarity	NPC54066
0.7656	Intermediate Similarity	NPC303951
0.7647	Intermediate Similarity	NPC182222
0.7641	Intermediate Similarity	NPC474798
0.7639	Intermediate Similarity	NPC122436
0.7638	Intermediate Similarity	NPC83111
0.7594	Intermediate Similarity	NPC16066
0.7586	Intermediate Similarity	NPC70956
0.7586	Intermediate Similarity	NPC243834
0.7583	Intermediate Similarity	NPC472098
0.7581	Intermediate Similarity	NPC323969
0.7581	Intermediate Similarity	NPC276657
0.7571	Intermediate Similarity	NPC309845
0.757	Intermediate Similarity	NPC473041
0.7565	Intermediate Similarity	NPC303225
0.7563	Intermediate Similarity	NPC84478
0.7559	Intermediate Similarity	NPC36405
0.7556	Intermediate Similarity	NPC148889
0.7549	Intermediate Similarity	NPC472284
0.7536	Intermediate Similarity	NPC82370
0.7536	Intermediate Similarity	NPC220337
0.7534	Intermediate Similarity	NPC57453
0.7526	Intermediate Similarity	NPC84347
0.7525	Intermediate Similarity	NPC314002
0.7523	Intermediate Similarity	NPC305984
0.7523	Intermediate Similarity	NPC21638
0.7512	Intermediate Similarity	NPC53344
0.7512	Intermediate Similarity	NPC138370
0.7512	Intermediate Similarity	NPC477979
0.75	Intermediate Similarity	NPC12344
0.7487	Intermediate Similarity	NPC184964
0.7477	Intermediate Similarity	NPC205372
0.7476	Intermediate Similarity	NPC329793
0.7476	Intermediate Similarity	NPC176538
0.7475	Intermediate Similarity	NPC204717
0.7468	Intermediate Similarity	NPC478083
0.7467	Intermediate Similarity	NPC470784
0.7455	Intermediate Similarity	NPC473187
0.7452	Intermediate Similarity	NPC162484
0.7449	Intermediate Similarity	NPC219336
0.7437	Intermediate Similarity	NPC42591
0.7436	Intermediate Similarity	NPC258048
0.7429	Intermediate Similarity	NPC183777
0.7424	Intermediate Similarity	NPC220765
0.7422	Intermediate Similarity	NPC184680
0.7418	Intermediate Similarity	NPC48353
0.7418	Intermediate Similarity	NPC316981
0.7413	Intermediate Similarity	NPC128751
0.7413	Intermediate Similarity	NPC246700
0.7406	Intermediate Similarity	NPC269367
0.7404	Intermediate Similarity	NPC216369
0.7404	Intermediate Similarity	NPC57398
0.74	Intermediate Similarity	NPC171171
0.7399	Intermediate Similarity	NPC207686
0.7398	Intermediate Similarity	NPC183662
0.7398	Intermediate Similarity	NPC15573
0.7398	Intermediate Similarity	NPC217372
0.7397	Intermediate Similarity	NPC314633
0.7395	Intermediate Similarity	NPC330009
0.7393	Intermediate Similarity	NPC266249
0.7389	Intermediate Similarity	NPC470785
0.7383	Intermediate Similarity	NPC266931
0.7382	Intermediate Similarity	NPC118511
0.7376	Intermediate Similarity	NPC106833
0.7376	Intermediate Similarity	NPC469497
0.7376	Intermediate Similarity	NPC257851
0.7373	Intermediate Similarity	NPC89549
0.7368	Intermediate Similarity	NPC317572
0.7366	Intermediate Similarity	NPC473105
0.7364	Intermediate Similarity	NPC97746
0.7363	Intermediate Similarity	NPC278434
0.7363	Intermediate Similarity	NPC66083
0.7361	Intermediate Similarity	NPC472285
0.7359	Intermediate Similarity	NPC91868
0.7359	Intermediate Similarity	NPC63971
0.7356	Intermediate Similarity	NPC471944
0.7354	Intermediate Similarity	NPC116573
0.7345	Intermediate Similarity	NPC235685
0.7342	Intermediate Similarity	NPC471762
0.7339	Intermediate Similarity	NPC132642
0.7333	Intermediate Similarity	NPC208898
0.7333	Intermediate Similarity	NPC474409
0.7331	Intermediate Similarity	NPC74619
0.733	Intermediate Similarity	NPC90229
0.7327	Intermediate Similarity	NPC131885
0.7325	Intermediate Similarity	NPC49672
0.7324	Intermediate Similarity	NPC123839
0.7323	Intermediate Similarity	NPC469896
0.7321	Intermediate Similarity	NPC475085
0.7321	Intermediate Similarity	NPC475112
0.7321	Intermediate Similarity	NPC291535

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 NPC321428 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	256
0.1-0.2	676
0.2-0.3	942
0.3-0.4	1304
0.4-0.5	2889
0.5-0.6	2185
0.6-0.7	787
0.7-0.8	104
0.8-0.85	7
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8269	Intermediate Similarity	NPD6160	Clinical (unspecified phase)
0.8137	Intermediate Similarity	NPD5416	Discontinued
0.8125	Intermediate Similarity	NPD3258	Approved
0.8091	Intermediate Similarity	NPD5483	Clinical (unspecified phase)
0.809	Intermediate Similarity	NPD484	Approved
0.8077	Intermediate Similarity	NPD5632	Approved
0.8019	Intermediate Similarity	NPD5417	Clinical (unspecified phase)
0.8019	Intermediate Similarity	NPD3257	Approved
0.7915	Intermediate Similarity	NPD6242	Discontinued
0.7909	Intermediate Similarity	NPD2921	Clinical (unspecified phase)
0.7879	Intermediate Similarity	NPD1038	Approved
0.7778	Intermediate Similarity	NPD4328	Approved
0.7761	Intermediate Similarity	NPD5003	Discontinued
0.7678	Intermediate Similarity	NPD7538	Clinical (unspecified phase)
0.7659	Intermediate Similarity	NPD2779	Approved
0.7642	Intermediate Similarity	NPD2433	Clinical (unspecified phase)
0.7638	Intermediate Similarity	NPD2565	Phase 2
0.7638	Intermediate Similarity	NPD2564	Approved
0.7632	Intermediate Similarity	NPD5482	Discontinued
0.7632	Intermediate Similarity	NPD2844	Phase 3
0.7624	Intermediate Similarity	NPD5512	Phase 3
0.7612	Intermediate Similarity	NPD1304	Clinical (unspecified phase)
0.7591	Intermediate Similarity	NPD1466	Phase 3
0.7591	Intermediate Similarity	NPD1867	Approved
0.7591	Intermediate Similarity	NPD1467	Approved
0.7588	Intermediate Similarity	NPD4558	Phase 2
0.7574	Intermediate Similarity	NPD3324	Clinical (unspecified phase)
0.7548	Intermediate Similarity	NPD2715	Clinical (unspecified phase)
0.7534	Intermediate Similarity	NPD3259	Approved
0.7512	Intermediate Similarity	NPD1768	Approved
0.7512	Intermediate Similarity	NPD4118	Clinical (unspecified phase)
0.7512	Intermediate Similarity	NPD2778	Approved
0.75	Intermediate Similarity	NPD5866	Approved
0.75	Intermediate Similarity	NPD2721	Clinical (unspecified phase)
0.7489	Intermediate Similarity	NPD2951	Discontinued
0.7488	Intermediate Similarity	NPD3354	Phase 2
0.7488	Intermediate Similarity	NPD7395	Discontinued
0.7488	Intermediate Similarity	NPD4418	Discontinued
0.7488	Intermediate Similarity	NPD4429	Discontinued
0.7477	Intermediate Similarity	NPD7547	Clinical (unspecified phase)
0.7462	Intermediate Similarity	NPD3178	Discontinued
0.7457	Intermediate Similarity	NPD8463	Approved
0.7455	Intermediate Similarity	NPD7853	Phase 2
0.7429	Intermediate Similarity	NPD5429	Discontinued
0.7406	Intermediate Similarity	NPD1166	Clinical (unspecified phase)
0.7399	Intermediate Similarity	NPD4885	Approved
0.7395	Intermediate Similarity	NPD5612	Discontinued
0.7387	Intermediate Similarity	NPD5479	Discontinued
0.7383	Intermediate Similarity	NPD3945	Discontinued
0.7378	Intermediate Similarity	NPD3006	Discontinued
0.7376	Intermediate Similarity	NPD7268	Clinical (unspecified phase)
0.7366	Intermediate Similarity	NPD4373	Phase 2
0.7333	Intermediate Similarity	NPD5901	Discontinued
0.7316	Intermediate Similarity	NPD3328	Phase 2
0.7311	Intermediate Similarity	NPD5658	Approved
0.7309	Intermediate Similarity	NPD4952	Phase 3
0.7309	Intermediate Similarity	NPD5801	Clinical (unspecified phase)
0.7309	Intermediate Similarity	NPD5022	Discontinued
0.73	Intermediate Similarity	NPD5083	Clinical (unspecified phase)
0.7299	Intermediate Similarity	NPD3003	Approved
0.7297	Intermediate Similarity	NPD7994	Phase 2
0.7294	Intermediate Similarity	NPD6974	Phase 3
0.7293	Intermediate Similarity	NPD6716	Phase 1
0.7277	Intermediate Similarity	NPD1505	Phase 2
0.7273	Intermediate Similarity	NPD6824	Clinical (unspecified phase)
0.7269	Intermediate Similarity	NPD4667	Clinical (unspecified phase)
0.7264	Intermediate Similarity	NPD7452	Approved
0.7264	Intermediate Similarity	NPD7222	Phase 2
0.7264	Intermediate Similarity	NPD1392	Approved
0.7264	Intermediate Similarity	NPD7453	Approved
0.7252	Intermediate Similarity	NPD3263	Phase 3
0.725	Intermediate Similarity	NPD5450	Discontinued
0.7243	Intermediate Similarity	NPD648	Clinical (unspecified phase)
0.723	Intermediate Similarity	NPD6376	Discontinued
0.7222	Intermediate Similarity	NPD3243	Approved
0.721	Intermediate Similarity	NPD8102	Discontinued
0.7209	Intermediate Similarity	NPD7703	Clinical (unspecified phase)
0.7204	Intermediate Similarity	NPD2920	Discontinued
0.7204	Intermediate Similarity	NPD2121	Clinical (unspecified phase)
0.72	Intermediate Similarity	NPD6962	Phase 2
0.7198	Intermediate Similarity	NPD5488	Discontinued
0.7196	Intermediate Similarity	NPD4506	Discontinued
0.7195	Intermediate Similarity	NPD6209	Approved
0.7182	Intermediate Similarity	NPD7180	Phase 3
0.7176	Intermediate Similarity	NPD6657	Clinical (unspecified phase)
0.7174	Intermediate Similarity	NPD7417	Discontinued
0.7172	Intermediate Similarity	NPD749	Clinical (unspecified phase)
0.7167	Intermediate Similarity	NPD8358	Approved
0.7156	Intermediate Similarity	NPD7589	Clinical (unspecified phase)
0.7155	Intermediate Similarity	NPD7708	Approved
0.715	Intermediate Similarity	NPD2189	Approved
0.715	Intermediate Similarity	NPD2187	Approved
0.7143	Intermediate Similarity	NPD1322	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD4845	Discontinued
0.7143	Intermediate Similarity	NPD7571	Clinical (unspecified phase)
0.7137	Intermediate Similarity	NPD5040	Clinical (unspecified phase)
0.7136	Intermediate Similarity	NPD4862	Clinical (unspecified phase)
0.713	Intermediate Similarity	NPD7470	Discontinued
0.7121	Intermediate Similarity	NPD4736	Clinical (unspecified phase)
0.7121	Intermediate Similarity	NPD482	Approved
0.7118	Intermediate Similarity	NPD4368	Phase 2
0.7118	Intermediate Similarity	NPD5805	Approved
0.7113	Intermediate Similarity	NPD1631	Approved
0.711	Intermediate Similarity	NPD1638	Discovery
0.7101	Intermediate Similarity	NPD5575	Clinical (unspecified phase)
0.7093	Intermediate Similarity	NPD6263	Clinical (unspecified phase)
0.7089	Intermediate Similarity	NPD6138	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD6531	Approved
0.7083	Intermediate Similarity	NPD6530	Approved
0.707	Intermediate Similarity	NPD2509	Approved
0.707	Intermediate Similarity	NPD2510	Approved
0.7059	Intermediate Similarity	NPD3875	Discontinued
0.7054	Intermediate Similarity	NPD6247	Clinical (unspecified phase)
0.7051	Intermediate Similarity	NPD4502	Phase 2
0.7051	Intermediate Similarity	NPD6567	Clinical (unspecified phase)
0.7037	Intermediate Similarity	NPD7803	Approved
0.7032	Intermediate Similarity	NPD5902	Approved
0.7032	Intermediate Similarity	NPD5903	Approved
0.7024	Intermediate Similarity	NPD4948	Discontinued
0.7018	Intermediate Similarity	NPD3746	Discontinued
0.701	Intermediate Similarity	NPD6344	Clinical (unspecified phase)
0.7009	Intermediate Similarity	NPD3947	Discontinued
0.7005	Intermediate Similarity	NPD3392	Approved
0.7	Intermediate Similarity	NPD3394	Approved
0.7	Intermediate Similarity	NPD3389	Approved
0.7	Intermediate Similarity	NPD3393	Approved
0.6995	Remote Similarity	NPD2095	Phase 2
0.6995	Remote Similarity	NPD2094	Phase 2
0.6995	Remote Similarity	NPD2092	Phase 2
0.699	Remote Similarity	NPD1534	Approved
0.6982	Remote Similarity	NPD6770	Approved
0.6981	Remote Similarity	NPD1739	Approved
0.6981	Remote Similarity	NPD1740	Approved
0.6981	Remote Similarity	NPD4500	Approved
0.6981	Remote Similarity	NPD4501	Approved
0.6978	Remote Similarity	NPD3925	Approved
0.6971	Remote Similarity	NPD7955	Approved
0.6971	Remote Similarity	NPD7956	Approved
0.697	Remote Similarity	NPD1573	Approved
0.697	Remote Similarity	NPD1575	Approved
0.6968	Remote Similarity	NPD5164	Discontinued
0.6967	Remote Similarity	NPD7946	Pre-registration
0.6964	Remote Similarity	NPD2285	Clinical (unspecified phase)
0.6961	Remote Similarity	NPD2096	Phase 2
0.6961	Remote Similarity	NPD2091	Phase 2
0.696	Remote Similarity	NPD7710	Clinical (unspecified phase)
0.6959	Remote Similarity	NPD1630	Approved
0.6955	Remote Similarity	NPD5293	Phase 2
0.6955	Remote Similarity	NPD4897	Phase 2
0.6955	Remote Similarity	NPD3757	Clinical (unspecified phase)
0.6952	Remote Similarity	NPD6550	Discontinued
0.6951	Remote Similarity	NPD8364	Approved
0.6951	Remote Similarity	NPD8363	Approved
0.6949	Remote Similarity	NPD7868	Clinical (unspecified phase)
0.6946	Remote Similarity	NPD4204	Approved
0.6946	Remote Similarity	NPD4203	Approved
0.6937	Remote Similarity	NPD8405	Clinical (unspecified phase)
0.6934	Remote Similarity	NPD3825	Phase 3
0.6931	Remote Similarity	NPD5398	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD8160	Phase 2
0.6923	Remote Similarity	NPD6517	Phase 3
0.6919	Remote Similarity	NPD6988	Phase 1
0.6913	Remote Similarity	NPD6741	Clinical (unspecified phase)
0.6912	Remote Similarity	NPD2916	Discontinued
0.6908	Remote Similarity	NPD2792	Approved
0.69	Remote Similarity	NPD750	Phase 2
0.6898	Remote Similarity	NPD1592	Phase 3
0.6897	Remote Similarity	NPD4958	Clinical (unspecified phase)
0.6895	Remote Similarity	NPD8365	Clinical (unspecified phase)
0.6891	Remote Similarity	NPD8101	Phase 3
0.6887	Remote Similarity	NPD772	Phase 3
0.6887	Remote Similarity	NPD4987	Clinical (unspecified phase)
0.6886	Remote Similarity	NPD5559	Phase 2
0.6884	Remote Similarity	NPD6176	Phase 1
0.6875	Remote Similarity	NPD4926	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD5850	Phase 3
0.6872	Remote Similarity	NPD7603	Discontinued
0.687	Remote Similarity	NPD7797	Approved
0.687	Remote Similarity	NPD7796	Approved
0.6864	Remote Similarity	NPD8097	Phase 3
0.6864	Remote Similarity	NPD8096	Phase 3
0.6861	Remote Similarity	NPD6985	Discontinued
0.686	Remote Similarity	NPD8091	Phase 3
0.6856	Remote Similarity	NPD5924	Discontinued
0.6853	Remote Similarity	NPD4454	Phase 2
0.6852	Remote Similarity	NPD8283	Approved
0.6852	Remote Similarity	NPD4033	Approved
0.6852	Remote Similarity	NPD4795	Phase 2
0.6852	Remote Similarity	NPD4038	Approved
0.6852	Remote Similarity	NPD56	Approved
0.6852	Remote Similarity	NPD4036	Approved
0.6852	Remote Similarity	NPD4037	Approved
0.6852	Remote Similarity	NPD4035	Approved
0.6852	Remote Similarity	NPD3946	Clinical (unspecified phase)
0.6852	Remote Similarity	NPD4039	Approved
0.6852	Remote Similarity	NPD8282	Approved
0.6852	Remote Similarity	NPD31	Approved
0.6852	Remote Similarity	NPD4122	Approved
0.6852	Remote Similarity	NPD4034	Approved
0.6852	Remote Similarity	NPD32	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