NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	161.05
Volume:	162.502
LogP:	2.127
LogD:	2.021
LogS:	-2.725
# Rotatable Bonds:	1
TPSA:	53.09
# H-Bond Aceptor:	3
# H-Bond Donor:	2
# Rings:	2
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.67
Synthetic Accessibility Score:	1.705
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:	-4.659
MDCK Permeability:	5.7560009736334905e-06
Pgp-inhibitor:	0.0
Pgp-substrate:	0.003
Human Intestinal Absorption (HIA):	0.017
20% Bioavailability (F20%):	0.002
30% Bioavailability (F30%):	0.921

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.548
Plasma Protein Binding (PPB):	68.19196319580078%
Volume Distribution (VD):	0.323
Pgp-substrate:	26.1390380859375%

ADMET: Metabolism

CYP1A2-inhibitor:	0.264
CYP1A2-substrate:	0.119
CYP2C19-inhibitor:	0.094
CYP2C19-substrate:	0.056
CYP2C9-inhibitor:	0.122
CYP2C9-substrate:	0.394
CYP2D6-inhibitor:	0.051
CYP2D6-substrate:	0.163
CYP3A4-inhibitor:	0.028
CYP3A4-substrate:	0.076

ADMET: Excretion

Clearance (CL):	3.567
Half-life (T1/2):	0.904

ADMET: Toxicity

hERG Blockers:	0.065
Human Hepatotoxicity (H-HT):	0.463
Drug-inuced Liver Injury (DILI):	0.908
AMES Toxicity:	0.008
Rat Oral Acute Toxicity:	0.911
Maximum Recommended Daily Dose:	0.025
Skin Sensitization:	0.257
Carcinogencity:	0.086
Eye Corrosion:	0.012
Eye Irritation:	0.987
Respiratory Toxicity:	0.746

Download Data

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

Natural Product: NPC278434

Natural Product ID:	NPC278434
*Common Name:**	Indole-3-Carboxylic Acid
IUPAC Name:	1H-indole-3-carboxylic acid
Synonyms:	Indole-3-Carboxylic Acid
Standard InCHIKey:	KMAKOBLIOCQGJP-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C9H7NO2/c11-9(12)7-5-10-8-4-2-1-3-6(7)8/h1-5,10H,(H,11,12)
SMILES:	c1ccc2c(c1)c(c[nH]2)C(=O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL387527
PubChem CID:	69867
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

☑ 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	13

Activity Type	# Activity
Cell Line	1
Individual Protein	1
NON-MOLECULAR	3
Organism	7
Others	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT153	Individual Protein	Androgen Receptor	Homo sapiens	Inhibition	=	1.0	%	PMID[534428]
NPT113	Cell Line	RAW264.7	Mus musculus	IC50	>	10000.0	nM	PMID[534431]
NPT27	Others	Unspecified		LogP app	=	-6.1	n.a.	PMID[534427]
NPT35	Others	n.a.		LogP	=	1.99	n.a.	PMID[534427]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Activity	=	0.092	n.a.	PMID[534429]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Activity	=	-10.1	n.a.	PMID[534429]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Activity	=	-6.5	n.a.	PMID[534429]
NPT20	Organism	Candida albicans	Candida albicans	Inhibition	=	6.48	%	PMID[534433]
NPT85	Organism	Filobasidiella neoformans	Cryptococcus neoformans	Inhibition	=	-9.05	%	PMID[534433]
NPT19	Organism	Escherichia coli	Escherichia coli	Inhibition	=	-2.29	%	PMID[534433]
NPT173	Organism	Klebsiella pneumoniae	Klebsiella pneumoniae	Inhibition	=	-9.13	%	PMID[534433]
NPT18	Organism	Pseudomonas aeruginosa	Pseudomonas aeruginosa	Inhibition	=	16.88	%	PMID[534433]
NPT747	Organism	Acinetobacter baumannii	Acinetobacter baumannii	Inhibition	=	1.08	%	PMID[534433]
NPT2922	Organism	Staphylococcus aureus subsp. aureus	Staphylococcus aureus subsp. aureus	Inhibition	=	-3.47	%	PMID[534433]

☑ 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 NPC278434 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	449
0.1-0.2	3826
0.2-0.3	12977
0.3-0.4	16206
0.4-0.5	4923
0.5-0.6	1719
0.6-0.7	1927
0.7-0.8	593
0.8-0.85	55
0.85-0.9	18
0.9-0.95	3
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9364	High Similarity	NPC138370
0.9086	High Similarity	NPC83111
0.887	High Similarity	NPC154339
0.8837	High Similarity	NPC111275
0.875	High Similarity	NPC282103
0.8722	High Similarity	NPC267343
0.871	High Similarity	NPC82053
0.8631	High Similarity	NPC131718
0.8617	High Similarity	NPC171787
0.8596	High Similarity	NPC78020
0.8588	High Similarity	NPC42372
0.8564	High Similarity	NPC183777
0.8557	High Similarity	NPC74360
0.8529	High Similarity	NPC102423
0.847	Intermediate Similarity	NPC202812
0.8466	Intermediate Similarity	NPC55772
0.8441	Intermediate Similarity	NPC213308
0.8438	Intermediate Similarity	NPC219087
0.8432	Intermediate Similarity	NPC474916
0.84	Intermediate Similarity	NPC203468
0.84	Intermediate Similarity	NPC149155
0.84	Intermediate Similarity	NPC110500
0.8396	Intermediate Similarity	NPC471944
0.8352	Intermediate Similarity	NPC267885
0.8295	Intermediate Similarity	NPC293216
0.8287	Intermediate Similarity	NPC315555
0.8268	Intermediate Similarity	NPC71037
0.8258	Intermediate Similarity	NPC283219
0.8258	Intermediate Similarity	NPC213468
0.8258	Intermediate Similarity	NPC126709
0.8258	Intermediate Similarity	NPC248041
0.8245	Intermediate Similarity	NPC45459
0.8245	Intermediate Similarity	NPC315491
0.8239	Intermediate Similarity	NPC313791
0.8235	Intermediate Similarity	NPC131887
0.8229	Intermediate Similarity	NPC266249
0.82	Intermediate Similarity	NPC229893
0.8196	Intermediate Similarity	NPC82370
0.8182	Intermediate Similarity	NPC90229
0.8144	Intermediate Similarity	NPC123839
0.8141	Intermediate Similarity	NPC276657
0.8138	Intermediate Similarity	NPC67288
0.8101	Intermediate Similarity	NPC284775
0.8098	Intermediate Similarity	NPC221873
0.8087	Intermediate Similarity	NPC62749
0.8085	Intermediate Similarity	NPC156704
0.8077	Intermediate Similarity	NPC477003
0.8066	Intermediate Similarity	NPC470677
0.8035	Intermediate Similarity	NPC230869
0.8	Intermediate Similarity	NPC14113
0.8	Intermediate Similarity	NPC145885
0.8	Intermediate Similarity	NPC84827
0.799	Intermediate Similarity	NPC27041
0.799	Intermediate Similarity	NPC472285
0.799	Intermediate Similarity	NPC88008
0.7989	Intermediate Similarity	NPC235684
0.7978	Intermediate Similarity	NPC110158
0.7976	Intermediate Similarity	NPC159856
0.7959	Intermediate Similarity	NPC309845
0.7943	Intermediate Similarity	NPC242116
0.7935	Intermediate Similarity	NPC280290
0.7927	Intermediate Similarity	NPC98715
0.7926	Intermediate Similarity	NPC88315
0.7923	Intermediate Similarity	NPC469358
0.791	Intermediate Similarity	NPC41717
0.7907	Intermediate Similarity	NPC469760
0.7907	Intermediate Similarity	NPC259644
0.7907	Intermediate Similarity	NPC73952
0.7907	Intermediate Similarity	NPC469763
0.7907	Intermediate Similarity	NPC469786
0.7907	Intermediate Similarity	NPC469765
0.7907	Intermediate Similarity	NPC25008
0.7903	Intermediate Similarity	NPC321708
0.7884	Intermediate Similarity	NPC157828
0.7884	Intermediate Similarity	NPC276517
0.7884	Intermediate Similarity	NPC195239
0.7876	Intermediate Similarity	NPC57398
0.7874	Intermediate Similarity	NPC469762
0.7861	Intermediate Similarity	NPC75540
0.7861	Intermediate Similarity	NPC212376
0.7861	Intermediate Similarity	NPC70922
0.7861	Intermediate Similarity	NPC211572
0.7861	Intermediate Similarity	NPC80597
0.7849	Intermediate Similarity	NPC46580
0.7842	Intermediate Similarity	NPC11445
0.7838	Intermediate Similarity	NPC314002
0.7826	Intermediate Similarity	NPC220765
0.7819	Intermediate Similarity	NPC476460
0.7816	Intermediate Similarity	NPC469785
0.7809	Intermediate Similarity	NPC114637
0.7806	Intermediate Similarity	NPC225821
0.7806	Intermediate Similarity	NPC46225
0.7802	Intermediate Similarity	NPC184964
0.7801	Intermediate Similarity	NPC227582
0.7801	Intermediate Similarity	NPC141454
0.7797	Intermediate Similarity	NPC311276
0.7796	Intermediate Similarity	NPC160381
0.7791	Intermediate Similarity	NPC105818
0.7791	Intermediate Similarity	NPC24678
0.779	Intermediate Similarity	NPC303225
0.7789	Intermediate Similarity	NPC118940
0.7784	Intermediate Similarity	NPC204717
0.7784	Intermediate Similarity	NPC322644
0.7784	Intermediate Similarity	NPC279918
0.7784	Intermediate Similarity	NPC207851
0.7778	Intermediate Similarity	NPC302647
0.7772	Intermediate Similarity	NPC191415
0.7772	Intermediate Similarity	NPC264285
0.7766	Intermediate Similarity	NPC127677
0.7766	Intermediate Similarity	NPC258062
0.7765	Intermediate Similarity	NPC314372
0.7762	Intermediate Similarity	NPC182222
0.776	Intermediate Similarity	NPC164340
0.7759	Intermediate Similarity	NPC33229
0.7751	Intermediate Similarity	NPC190296
0.7751	Intermediate Similarity	NPC207686
0.774	Intermediate Similarity	NPC282231
0.7732	Intermediate Similarity	NPC300183
0.773	Intermediate Similarity	NPC48938
0.773	Intermediate Similarity	NPC102755
0.7705	Intermediate Similarity	NPC219848
0.7705	Intermediate Similarity	NPC96890
0.7701	Intermediate Similarity	NPC171171
0.7684	Intermediate Similarity	NPC67551
0.768	Intermediate Similarity	NPC273532
0.768	Intermediate Similarity	NPC252338
0.7673	Intermediate Similarity	NPC36405
0.7663	Intermediate Similarity	NPC256268
0.7661	Intermediate Similarity	NPC167400
0.7656	Intermediate Similarity	NPC179701
0.7653	Intermediate Similarity	NPC134848
0.7653	Intermediate Similarity	NPC165599
0.765	Intermediate Similarity	NPC72956
0.7647	Intermediate Similarity	NPC311282
0.7644	Intermediate Similarity	NPC326422
0.7644	Intermediate Similarity	NPC304203
0.7638	Intermediate Similarity	NPC271862
0.7634	Intermediate Similarity	NPC243058
0.7629	Intermediate Similarity	NPC293917
0.7626	Intermediate Similarity	NPC244741
0.7626	Intermediate Similarity	NPC193238
0.7621	Intermediate Similarity	NPC16352
0.7617	Intermediate Similarity	NPC74153
0.7617	Intermediate Similarity	NPC272483
0.7617	Intermediate Similarity	NPC262898
0.7614	Intermediate Similarity	NPC141353
0.7612	Intermediate Similarity	NPC471194
0.7612	Intermediate Similarity	NPC471193
0.7612	Intermediate Similarity	NPC151976
0.7612	Intermediate Similarity	NPC6865
0.7612	Intermediate Similarity	NPC153980
0.7612	Intermediate Similarity	NPC110182
0.7612	Intermediate Similarity	NPC87856
0.7611	Intermediate Similarity	NPC49954
0.7611	Intermediate Similarity	NPC54988
0.7611	Intermediate Similarity	NPC160105
0.7611	Intermediate Similarity	NPC474561
0.7609	Intermediate Similarity	NPC183662
0.7609	Intermediate Similarity	NPC217372
0.7609	Intermediate Similarity	NPC15573
0.7604	Intermediate Similarity	NPC178858
0.7602	Intermediate Similarity	NPC476874
0.7602	Intermediate Similarity	NPC476073
0.7598	Intermediate Similarity	NPC40779
0.7594	Intermediate Similarity	NPC228835
0.7592	Intermediate Similarity	NPC99666
0.7592	Intermediate Similarity	NPC47190
0.7574	Intermediate Similarity	NPC267965
0.7574	Intermediate Similarity	NPC229348
0.7573	Intermediate Similarity	NPC2395
0.7569	Intermediate Similarity	NPC63751
0.7568	Intermediate Similarity	NPC276540
0.7568	Intermediate Similarity	NPC219336
0.7568	Intermediate Similarity	NPC233050
0.7568	Intermediate Similarity	NPC42979
0.7568	Intermediate Similarity	NPC11126
0.7565	Intermediate Similarity	NPC472293
0.756	Intermediate Similarity	NPC114310
0.7556	Intermediate Similarity	NPC115232
0.7554	Intermediate Similarity	NPC224764
0.7552	Intermediate Similarity	NPC473821
0.7548	Intermediate Similarity	NPC476818
0.7542	Intermediate Similarity	NPC214106
0.7541	Intermediate Similarity	NPC314603
0.7538	Intermediate Similarity	NPC477004
0.7538	Intermediate Similarity	NPC270918
0.753	Intermediate Similarity	NPC194541
0.7528	Intermediate Similarity	NPC135141
0.7528	Intermediate Similarity	NPC92796
0.7513	Intermediate Similarity	NPC90415
0.7513	Intermediate Similarity	NPC94752
0.75	Intermediate Similarity	NPC132211
0.75	Intermediate Similarity	NPC279189
0.75	Intermediate Similarity	NPC39679
0.75	Intermediate Similarity	NPC203635
0.75	Intermediate Similarity	NPC200553
0.75	Intermediate Similarity	NPC472292
0.75	Intermediate Similarity	NPC96102
0.75	Intermediate Similarity	NPC204491
0.75	Intermediate Similarity	NPC471192

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 NPC278434 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	259
0.1-0.2	641
0.2-0.3	852
0.3-0.4	1709
0.4-0.5	2613
0.5-0.6	1968
0.6-0.7	937
0.7-0.8	157
0.8-0.85	12
0.85-0.9	2
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8804	High Similarity	NPD2121	Clinical (unspecified phase)
0.8617	High Similarity	NPD2509	Approved
0.8617	High Similarity	NPD2510	Approved
0.8556	High Similarity	NPD5901	Discontinued
0.84	Intermediate Similarity	NPD482	Approved
0.8371	Intermediate Similarity	NPD3178	Discontinued
0.8352	Intermediate Similarity	NPD749	Clinical (unspecified phase)
0.8308	Intermediate Similarity	NPD3393	Approved
0.8308	Intermediate Similarity	NPD3389	Approved
0.8308	Intermediate Similarity	NPD3394	Approved
0.8278	Intermediate Similarity	NPD2091	Phase 2
0.8278	Intermediate Similarity	NPD2096	Phase 2
0.8245	Intermediate Similarity	NPD484	Approved
0.8242	Intermediate Similarity	NPD4948	Discontinued
0.8222	Intermediate Similarity	NPD2092	Phase 2
0.8222	Intermediate Similarity	NPD2094	Phase 2
0.8222	Intermediate Similarity	NPD2095	Phase 2
0.8122	Intermediate Similarity	NPD5728	Clinical (unspecified phase)
0.8034	Intermediate Similarity	NPD750	Phase 2
0.7989	Intermediate Similarity	NPD5065	Approved
0.7958	Intermediate Similarity	NPD8248	Clinical (unspecified phase)
0.7828	Intermediate Similarity	NPD5475	Discontinued
0.7795	Intermediate Similarity	NPD6987	Phase 1
0.7789	Intermediate Similarity	NPD5975	Clinical (unspecified phase)
0.7755	Intermediate Similarity	NPD4862	Clinical (unspecified phase)
0.775	Intermediate Similarity	NPD3795	Approved
0.775	Intermediate Similarity	NPD3794	Approved
0.7722	Intermediate Similarity	NPD1573	Approved
0.7722	Intermediate Similarity	NPD1575	Approved
0.7716	Intermediate Similarity	NPD6838	Clinical (unspecified phase)
0.7714	Intermediate Similarity	NPD276	Clinical (unspecified phase)
0.7704	Intermediate Similarity	NPD3947	Discontinued
0.77	Intermediate Similarity	NPD8093	Discontinued
0.7688	Intermediate Similarity	NPD7998	Clinical (unspecified phase)
0.7667	Intermediate Similarity	NPD2844	Phase 3
0.7662	Intermediate Similarity	NPD8094	Discontinued
0.7661	Intermediate Similarity	NPD9075	Approved
0.7661	Intermediate Similarity	NPD9074	Approved
0.765	Intermediate Similarity	NPD7470	Discontinued
0.7632	Intermediate Similarity	NPD5592	Clinical (unspecified phase)
0.7629	Intermediate Similarity	NPD7621	Clinical (unspecified phase)
0.7598	Intermediate Similarity	NPD1631	Approved
0.7594	Intermediate Similarity	NPD3607	Clinical (unspecified phase)
0.7577	Intermediate Similarity	NPD4987	Clinical (unspecified phase)
0.7568	Intermediate Similarity	NPD5398	Clinical (unspecified phase)
0.7563	Intermediate Similarity	NPD6176	Phase 1
0.756	Intermediate Similarity	NPD4845	Discontinued
0.7539	Intermediate Similarity	NPD6180	Clinical (unspecified phase)
0.7539	Intermediate Similarity	NPD2336	Approved
0.7527	Intermediate Similarity	NPD4184	Clinical (unspecified phase)
0.7525	Intermediate Similarity	NPD5426	Phase 3
0.7524	Intermediate Similarity	NPD6242	Discontinued
0.7513	Intermediate Similarity	NPD4426	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD198	Clinical (unspecified phase)
0.7461	Intermediate Similarity	NPD5575	Clinical (unspecified phase)
0.7461	Intermediate Similarity	NPD1173	Approved
0.7449	Intermediate Similarity	NPD6999	Discontinued
0.7449	Intermediate Similarity	NPD7000	Clinical (unspecified phase)
0.744	Intermediate Similarity	NPD3280	Approved
0.7438	Intermediate Similarity	NPD3917	Approved
0.7438	Intermediate Similarity	NPD3918	Approved
0.7438	Intermediate Similarity	NPD3916	Clinical (unspecified phase)
0.7438	Intermediate Similarity	NPD6657	Clinical (unspecified phase)
0.7432	Intermediate Similarity	NPD1326	Approved
0.7432	Intermediate Similarity	NPD1325	Approved
0.743	Intermediate Similarity	NPD1630	Approved
0.7427	Intermediate Similarity	NPD107	Approved
0.7416	Intermediate Similarity	NPD3222	Phase 2
0.7415	Intermediate Similarity	NPD6733	Discontinued
0.7403	Intermediate Similarity	NPD5140	Approved
0.7403	Intermediate Similarity	NPD5138	Approved
0.74	Intermediate Similarity	NPD2715	Clinical (unspecified phase)
0.7394	Intermediate Similarity	NPD1783	Clinical (unspecified phase)
0.7389	Intermediate Similarity	NPD3915	Approved
0.7385	Intermediate Similarity	NPD2307	Discontinued
0.7384	Intermediate Similarity	NPD1592	Phase 3
0.7377	Intermediate Similarity	NPD5069	Clinical (unspecified phase)
0.7371	Intermediate Similarity	NPD1038	Approved
0.7371	Intermediate Similarity	NPD802	Phase 2
0.7368	Intermediate Similarity	NPD786	Approved
0.7353	Intermediate Similarity	NPD8096	Phase 3
0.7353	Intermediate Similarity	NPD8097	Phase 3
0.735	Intermediate Similarity	NPD2721	Clinical (unspecified phase)
0.735	Intermediate Similarity	NPD6323	Clinical (unspecified phase)
0.7347	Intermediate Similarity	NPD5003	Discontinued
0.7347	Intermediate Similarity	NPD7948	Phase 1
0.7343	Intermediate Similarity	NPD7878	Phase 2
0.7337	Intermediate Similarity	NPD8073	Approved
0.7327	Intermediate Similarity	NPD7947	Clinical (unspecified phase)
0.7326	Intermediate Similarity	NPD2144	Approved
0.7324	Intermediate Similarity	NPD5801	Clinical (unspecified phase)
0.732	Intermediate Similarity	NPD6665	Discontinued
0.7315	Intermediate Similarity	NPD3006	Discontinued
0.7313	Intermediate Similarity	NPD6732	Clinical (unspecified phase)
0.7313	Intermediate Similarity	NPD7001	Phase 3
0.7308	Intermediate Similarity	NPD7404	Approved
0.7306	Intermediate Similarity	NPD4499	Approved
0.73	Intermediate Similarity	NPD8072	Approved
0.7296	Intermediate Similarity	NPD4848	Phase 1
0.7283	Intermediate Similarity	NPD1722	Approved
0.7273	Intermediate Similarity	NPD6137	Clinical (unspecified phase)
0.7268	Intermediate Similarity	NPD6630	Clinical (unspecified phase)
0.7264	Intermediate Similarity	NPD944	Approved
0.726	Intermediate Similarity	NPD8405	Clinical (unspecified phase)
0.7249	Intermediate Similarity	NPD6595	Phase 3
0.7249	Intermediate Similarity	NPD1291	Clinical (unspecified phase)
0.7231	Intermediate Similarity	NPD3404	Approved
0.7231	Intermediate Similarity	NPD4922	Phase 2
0.7231	Intermediate Similarity	NPD5505	Discontinued
0.723	Intermediate Similarity	NPD6165	Phase 2
0.723	Intermediate Similarity	NPD6164	Phase 2
0.7228	Intermediate Similarity	NPD2008	Discontinued
0.7228	Intermediate Similarity	NPD7010	Phase 3
0.7225	Intermediate Similarity	NPD1096	Discontinued
0.7225	Intermediate Similarity	NPD6178	Phase 3
0.7217	Intermediate Similarity	NPD7269	Clinical (unspecified phase)
0.7216	Intermediate Similarity	NPD2564	Approved
0.7216	Intermediate Similarity	NPD2565	Phase 2
0.7211	Intermediate Similarity	NPD3038	Discontinued
0.7209	Intermediate Similarity	NPD203	Clinical (unspecified phase)
0.7209	Intermediate Similarity	NPD2896	Discontinued
0.7206	Intermediate Similarity	NPD4506	Discontinued
0.7198	Intermediate Similarity	NPD5293	Phase 2
0.7198	Intermediate Similarity	NPD8112	Clinical (unspecified phase)
0.7196	Intermediate Similarity	NPD1587	Approved
0.7196	Intermediate Similarity	NPD4076	Approved
0.7196	Intermediate Similarity	NPD4079	Approved
0.7191	Intermediate Similarity	NPD4462	Approved
0.7191	Intermediate Similarity	NPD4463	Approved
0.719	Intermediate Similarity	NPD1996	Discontinued
0.7184	Intermediate Similarity	NPD1625	Approved
0.7175	Intermediate Similarity	NPD9271	Approved
0.7174	Intermediate Similarity	NPD1568	Clinical (unspecified phase)
0.7171	Intermediate Similarity	NPD7825	Clinical (unspecified phase)
0.7167	Intermediate Similarity	NPD5257	Clinical (unspecified phase)
0.7165	Intermediate Similarity	NPD1534	Approved
0.7158	Intermediate Similarity	NPD2479	Phase 3
0.7158	Intermediate Similarity	NPD2481	Approved
0.7157	Intermediate Similarity	NPD7618	Phase 3
0.7157	Intermediate Similarity	NPD7619	Phase 3
0.7157	Intermediate Similarity	NPD7666	Phase 3
0.7157	Intermediate Similarity	NPD7665	Phase 2
0.7143	Intermediate Similarity	NPD3506	Approved
0.7143	Intermediate Similarity	NPD3505	Approved
0.7136	Intermediate Similarity	NPD8013	Clinical (unspecified phase)
0.7121	Intermediate Similarity	NPD7818	Clinical (unspecified phase)
0.712	Intermediate Similarity	NPD5088	Discontinued
0.7115	Intermediate Similarity	NPD7970	Approved
0.7115	Intermediate Similarity	NPD3757	Clinical (unspecified phase)
0.7115	Intermediate Similarity	NPD7971	Clinical (unspecified phase)
0.7109	Intermediate Similarity	NPD5827	Discontinued
0.7107	Intermediate Similarity	NPD1304	Clinical (unspecified phase)
0.7105	Intermediate Similarity	NPD8304	Clinical (unspecified phase)
0.7103	Intermediate Similarity	NPD7603	Discontinued
0.7101	Intermediate Similarity	NPD7594	Clinical (unspecified phase)
0.7095	Intermediate Similarity	NPD5632	Approved
0.7083	Intermediate Similarity	NPD3320	Approved
0.7083	Intermediate Similarity	NPD3318	Approved
0.7083	Intermediate Similarity	NPD3319	Phase 1
0.7079	Intermediate Similarity	NPD4702	Approved
0.7079	Intermediate Similarity	NPD4703	Approved
0.7077	Intermediate Similarity	NPD8110	Clinical (unspecified phase)
0.7068	Intermediate Similarity	NPD5473	Discontinued
0.7067	Intermediate Similarity	NPD3243	Approved
0.7065	Intermediate Similarity	NPD2305	Discontinued
0.7064	Intermediate Similarity	NPD5040	Clinical (unspecified phase)
0.7062	Intermediate Similarity	NPD6770	Approved
0.7062	Intermediate Similarity	NPD706	Phase 1
0.7059	Intermediate Similarity	NPD2921	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD7958	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD7957	Phase 1
0.7056	Intermediate Similarity	NPD4376	Phase 3
0.7053	Intermediate Similarity	NPD5416	Discontinued
0.7053	Intermediate Similarity	NPD6203	Clinical (unspecified phase)
0.7048	Intermediate Similarity	NPD8406	Clinical (unspecified phase)
0.7047	Intermediate Similarity	NPD7564	Discontinued
0.7039	Intermediate Similarity	NPD3100	Discontinued
0.7039	Intermediate Similarity	NPD6529	Discontinued
0.7039	Intermediate Similarity	NPD4374	Clinical (unspecified phase)
0.7037	Intermediate Similarity	NPD1586	Approved
0.7031	Intermediate Similarity	NPD4383	Clinical (unspecified phase)
0.703	Intermediate Similarity	NPD7903	Clinical (unspecified phase)
0.7029	Intermediate Similarity	NPD1189	Approved
0.7026	Intermediate Similarity	NPD6141	Clinical (unspecified phase)
0.7026	Intermediate Similarity	NPD8431	Approved
0.7019	Intermediate Similarity	NPD2411	Approved
0.7019	Intermediate Similarity	NPD4852	Phase 2
0.7014	Intermediate Similarity	NPD4429	Discontinued
0.701	Intermediate Similarity	NPD6610	Clinical (unspecified phase)
0.701	Intermediate Similarity	NPD8098	Approved
0.701	Intermediate Similarity	NPD6138	Clinical (unspecified phase)
0.7009	Intermediate Similarity	NPD6173	Approved
0.7005	Intermediate Similarity	NPD4051	Discontinued
0.7005	Intermediate Similarity	NPD7809	Clinical (unspecified phase)
0.7005	Intermediate Similarity	NPD1343	Approved
0.7	Intermediate Similarity	NPD4075	Phase 2
0.7	Intermediate Similarity	NPD2172	Phase 1
0.7	Intermediate Similarity	NPD6664	Approved
0.6995	Remote Similarity	NPD4345	Clinical (unspecified phase)
0.6995	Remote Similarity	NPD820	Phase 3

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