NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	209.12
Volume:	237.505
LogP:	4.605
LogD:	4.314
LogS:	-5.666
# Rotatable Bonds:	1
TPSA:	15.79
# H-Bond Aceptor:	1
# H-Bond Donor:	1
# Rings:	3
# Heavy Atoms:	1

MedChem Properties

QED Drug-Likeness Score:	0.609
Synthetic Accessibility Score:	1.881
Fsp3:	0.2
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.767
MDCK Permeability:	1.570928725413978e-05
Pgp-inhibitor:	0.151
Pgp-substrate:	0.182
Human Intestinal Absorption (HIA):	0.006
20% Bioavailability (F20%):	0.954
30% Bioavailability (F30%):	0.974

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.548
Plasma Protein Binding (PPB):	97.22489166259766%
Volume Distribution (VD):	2.394
Pgp-substrate:	1.1317083835601807%

ADMET: Metabolism

CYP1A2-inhibitor:	0.99
CYP1A2-substrate:	0.855
CYP2C19-inhibitor:	0.736
CYP2C19-substrate:	0.449
CYP2C9-inhibitor:	0.694
CYP2C9-substrate:	0.871
CYP2D6-inhibitor:	0.913
CYP2D6-substrate:	0.75
CYP3A4-inhibitor:	0.617
CYP3A4-substrate:	0.441

ADMET: Excretion

Clearance (CL):	3.903
Half-life (T1/2):	0.2

ADMET: Toxicity

hERG Blockers:	0.016
Human Hepatotoxicity (H-HT):	0.111
Drug-inuced Liver Injury (DILI):	0.825
AMES Toxicity:	0.4
Rat Oral Acute Toxicity:	0.157
Maximum Recommended Daily Dose:	0.513
Skin Sensitization:	0.64
Carcinogencity:	0.704
Eye Corrosion:	0.104
Eye Irritation:	0.988
Respiratory Toxicity:	0.957

Download Data

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

Natural Product: NPC475428

Natural Product ID:	NPC475428
*Common Name:**	1-Propan-2-Yl-9H-Carbazole
IUPAC Name:	1-propan-2-yl-9H-carbazole
Synonyms:
Standard InCHIKey:	ZTOFNRMEKUYYOE-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C15H15N/c1-10(2)11-7-5-8-13-12-6-3-4-9-14(12)16-15(11)13/h3-10,16H,1-2H3
SMILES:	CC(C)C1=CC=CC2=C1NC3=CC=CC=C23
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL505444
PubChem CID:	44576081
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000211] Indoles and derivatives [CHEMONTID:0000210] Carbazoles

*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
NPO2833	Cribricellina cribraria	Species	Catenicellidae	Eukaryota	n.a.	n.a.	n.a.	PMID[1791472]
NPO2833	Cribricellina cribraria	Species	Catenicellidae	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
MIC	6

Activity Type	# Activity
Cell Line	1
Organism	6

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT168	Cell Line	P388	Mus musculus	IC50	=	13.0	ug.mL-1	PMID[556194]
NPT19	Organism	Escherichia coli	Escherichia coli	MIC	>	120.0	ug	PMID[556194]
NPT79	Organism	Bacillus subtilis	Bacillus subtilis	MIC	=	7.5	ug	PMID[556194]
NPT18	Organism	Pseudomonas aeruginosa	Pseudomonas aeruginosa	MIC	>	60.0	ug	PMID[556194]
NPT20	Organism	Candida albicans	Candida albicans	MIC	=	1.9	ug	PMID[556194]
NPT330	Organism	Trichophyton mentagrophytes	Trichophyton mentagrophytes	MIC	=	0.45	ug	PMID[556194]
NPT1223	Organism	Amorphotheca resinae	Amorphotheca resinae	MIC	=	15.0	ug	PMID[556194]

☑ 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 NPC475428 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	1124
0.1-0.2	11167
0.2-0.3	17651
0.3-0.4	7392
0.4-0.5	2378
0.5-0.6	1555
0.6-0.7	994
0.7-0.8	345
0.8-0.85	59
0.85-0.9	22
0.9-0.95	3
0.95-1	7

Similarity Score	Similarity Level	Natural Product ID
0.9919	High Similarity	NPC473587
0.9837	High Similarity	NPC473762
0.976	High Similarity	NPC475450
0.976	High Similarity	NPC179365
0.9675	High Similarity	NPC250361
0.9528	High Similarity	NPC473930
0.935	High Similarity	NPC41174
0.9219	High Similarity	NPC22079
0.9098	High Similarity	NPC312092
0.8939	High Similarity	NPC198988
0.8872	High Similarity	NPC325252
0.875	High Similarity	NPC59084
0.875	High Similarity	NPC115611
0.8731	High Similarity	NPC29886
0.8731	High Similarity	NPC261195
0.8686	High Similarity	NPC473868
0.8686	High Similarity	NPC63157
0.8667	High Similarity	NPC84911
0.8643	High Similarity	NPC477134
0.8613	High Similarity	NPC2949
0.8613	High Similarity	NPC284635
0.8605	High Similarity	NPC122718
0.8593	High Similarity	NPC218268
0.8593	High Similarity	NPC96102
0.8583	High Similarity	NPC215519
0.8571	High Similarity	NPC162689
0.8571	High Similarity	NPC54102
0.856	High Similarity	NPC148140
0.854	High Similarity	NPC73767
0.854	High Similarity	NPC88097
0.854	High Similarity	NPC110126
0.8529	High Similarity	NPC105127
0.8521	High Similarity	NPC33421
0.8521	High Similarity	NPC53947
0.8511	High Similarity	NPC21605
0.8492	Intermediate Similarity	NPC81561
0.8478	Intermediate Similarity	NPC469784
0.8478	Intermediate Similarity	NPC469779
0.8478	Intermediate Similarity	NPC469768
0.8478	Intermediate Similarity	NPC469780
0.8478	Intermediate Similarity	NPC469767
0.8478	Intermediate Similarity	NPC469783
0.8478	Intermediate Similarity	NPC469761
0.8451	Intermediate Similarity	NPC124005
0.844	Intermediate Similarity	NPC288838
0.8433	Intermediate Similarity	NPC82295
0.8429	Intermediate Similarity	NPC242556
0.8417	Intermediate Similarity	NPC469766
0.8394	Intermediate Similarity	NPC125746
0.838	Intermediate Similarity	NPC179787
0.838	Intermediate Similarity	NPC201380
0.8369	Intermediate Similarity	NPC470440
0.8357	Intermediate Similarity	NPC190296
0.8345	Intermediate Similarity	NPC279081
0.8322	Intermediate Similarity	NPC321911
0.831	Intermediate Similarity	NPC63545
0.8299	Intermediate Similarity	NPC474791
0.8252	Intermediate Similarity	NPC469811
0.8243	Intermediate Similarity	NPC215584
0.8243	Intermediate Similarity	NPC44773
0.8239	Intermediate Similarity	NPC204141
0.8239	Intermediate Similarity	NPC314372
0.8231	Intermediate Similarity	NPC286427
0.8231	Intermediate Similarity	NPC76982
0.8219	Intermediate Similarity	NPC38736
0.8214	Intermediate Similarity	NPC230002
0.8194	Intermediate Similarity	NPC187951
0.8194	Intermediate Similarity	NPC37548
0.8182	Intermediate Similarity	NPC129042
0.8182	Intermediate Similarity	NPC143872
0.8176	Intermediate Similarity	NPC221786
0.8176	Intermediate Similarity	NPC475990
0.8176	Intermediate Similarity	NPC41257
0.8176	Intermediate Similarity	NPC206819
0.8176	Intermediate Similarity	NPC474880
0.8176	Intermediate Similarity	NPC318065
0.8176	Intermediate Similarity	NPC56765
0.8163	Intermediate Similarity	NPC184476
0.8151	Intermediate Similarity	NPC325903
0.8138	Intermediate Similarity	NPC148592
0.8125	Intermediate Similarity	NPC471957
0.8121	Intermediate Similarity	NPC229173
0.8112	Intermediate Similarity	NPC159856
0.8108	Intermediate Similarity	NPC216643
0.8082	Intermediate Similarity	NPC470233
0.8069	Intermediate Similarity	NPC2272
0.8014	Intermediate Similarity	NPC24678
0.8014	Intermediate Similarity	NPC105818
0.8013	Intermediate Similarity	NPC162799
0.8013	Intermediate Similarity	NPC90723
0.8	Intermediate Similarity	NPC473320
0.7987	Intermediate Similarity	NPC236711
0.7973	Intermediate Similarity	NPC470507
0.7973	Intermediate Similarity	NPC471458
0.7959	Intermediate Similarity	NPC470823
0.7947	Intermediate Similarity	NPC16667
0.7933	Intermediate Similarity	NPC135141
0.7933	Intermediate Similarity	NPC92796
0.7919	Intermediate Similarity	NPC285469
0.7905	Intermediate Similarity	NPC141926
0.7905	Intermediate Similarity	NPC469760
0.7905	Intermediate Similarity	NPC73952
0.7905	Intermediate Similarity	NPC469763
0.7905	Intermediate Similarity	NPC469786
0.7905	Intermediate Similarity	NPC259644
0.7905	Intermediate Similarity	NPC200214
0.7905	Intermediate Similarity	NPC469765
0.7905	Intermediate Similarity	NPC25008
0.7895	Intermediate Similarity	NPC271734
0.7867	Intermediate Similarity	NPC299594
0.7857	Intermediate Similarity	NPC154293
0.7857	Intermediate Similarity	NPC201700
0.7852	Intermediate Similarity	NPC75540
0.7852	Intermediate Similarity	NPC212376
0.7852	Intermediate Similarity	NPC207726
0.7852	Intermediate Similarity	NPC34844
0.7852	Intermediate Similarity	NPC80597
0.7852	Intermediate Similarity	NPC70922
0.7852	Intermediate Similarity	NPC211572
0.7838	Intermediate Similarity	NPC216713
0.7817	Intermediate Similarity	NPC169433
0.7806	Intermediate Similarity	NPC474897
0.7806	Intermediate Similarity	NPC194411
0.78	Intermediate Similarity	NPC141353
0.7794	Intermediate Similarity	NPC476140
0.7785	Intermediate Similarity	NPC161108
0.7778	Intermediate Similarity	NPC317105
0.7778	Intermediate Similarity	NPC21174
0.7778	Intermediate Similarity	NPC271797
0.7763	Intermediate Similarity	NPC122141
0.7763	Intermediate Similarity	NPC470204
0.7762	Intermediate Similarity	NPC104483
0.7756	Intermediate Similarity	NPC6982
0.7746	Intermediate Similarity	NPC251722
0.7746	Intermediate Similarity	NPC150259
0.7746	Intermediate Similarity	NPC314102
0.7733	Intermediate Similarity	NPC476297
0.7733	Intermediate Similarity	NPC476219
0.7727	Intermediate Similarity	NPC115232
0.7712	Intermediate Similarity	NPC470203
0.7712	Intermediate Similarity	NPC282231
0.7707	Intermediate Similarity	NPC97525
0.7704	Intermediate Similarity	NPC46358
0.7697	Intermediate Similarity	NPC67056
0.7692	Intermediate Similarity	NPC280548
0.7687	Intermediate Similarity	NPC316069
0.7682	Intermediate Similarity	NPC469785
0.7677	Intermediate Similarity	NPC474561
0.7677	Intermediate Similarity	NPC49954
0.7667	Intermediate Similarity	NPC232798
0.7662	Intermediate Similarity	NPC472587
0.7662	Intermediate Similarity	NPC8104
0.7658	Intermediate Similarity	NPC37423
0.7658	Intermediate Similarity	NPC189812
0.7658	Intermediate Similarity	NPC329688
0.7658	Intermediate Similarity	NPC275305
0.7647	Intermediate Similarity	NPC279918
0.7635	Intermediate Similarity	NPC114209
0.7635	Intermediate Similarity	NPC470111
0.7632	Intermediate Similarity	NPC469762
0.7628	Intermediate Similarity	NPC63751
0.7625	Intermediate Similarity	NPC88363
0.7613	Intermediate Similarity	NPC274229
0.761	Intermediate Similarity	NPC280852
0.7603	Intermediate Similarity	NPC20144
0.7597	Intermediate Similarity	NPC214106
0.7595	Intermediate Similarity	NPC477611
0.7595	Intermediate Similarity	NPC34508
0.7582	Intermediate Similarity	NPC230869
0.7568	Intermediate Similarity	NPC478186
0.7564	Intermediate Similarity	NPC109447
0.7564	Intermediate Similarity	NPC160105
0.7562	Intermediate Similarity	NPC68354
0.7562	Intermediate Similarity	NPC151939
0.7559	Intermediate Similarity	NPC302790
0.755	Intermediate Similarity	NPC200743
0.7548	Intermediate Similarity	NPC40779
0.7548	Intermediate Similarity	NPC247987
0.7548	Intermediate Similarity	NPC194640
0.7548	Intermediate Similarity	NPC311276
0.7532	Intermediate Similarity	NPC131718
0.7532	Intermediate Similarity	NPC82331
0.7516	Intermediate Similarity	NPC6093
0.7516	Intermediate Similarity	NPC213468
0.7516	Intermediate Similarity	NPC176199
0.7516	Intermediate Similarity	NPC317430
0.7516	Intermediate Similarity	NPC215795
0.75	Intermediate Similarity	NPC470508
0.75	Intermediate Similarity	NPC280864
0.75	Intermediate Similarity	NPC288785
0.75	Intermediate Similarity	NPC474958
0.75	Intermediate Similarity	NPC17751
0.7485	Intermediate Similarity	NPC212535
0.7484	Intermediate Similarity	NPC472123
0.7484	Intermediate Similarity	NPC474409
0.7469	Intermediate Similarity	NPC198339
0.7469	Intermediate Similarity	NPC300688
0.7468	Intermediate Similarity	NPC97343
0.7466	Intermediate Similarity	NPC238499
0.7452	Intermediate Similarity	NPC470509

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 NPC475428 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	520
0.1-0.2	775
0.2-0.3	1083
0.3-0.4	2148
0.4-0.5	2418
0.5-0.6	1549
0.6-0.7	541
0.7-0.8	95
0.8-0.85	15
0.85-0.9	5
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8971	High Similarity	NPD5254	Discontinued
0.8947	High Similarity	NPD1262	Discovery
0.8889	High Similarity	NPD3943	Clinical (unspecified phase)
0.8593	High Similarity	NPD198	Clinical (unspecified phase)
0.8551	High Similarity	NPD1722	Approved
0.854	High Similarity	NPD786	Approved
0.8519	High Similarity	NPD4880	Discontinued
0.8451	Intermediate Similarity	NPD3100	Discontinued
0.844	Intermediate Similarity	NPD1528	Clinical (unspecified phase)
0.8392	Intermediate Similarity	NPD4463	Approved
0.8392	Intermediate Similarity	NPD4462	Approved
0.8357	Intermediate Similarity	NPD4637	Clinical (unspecified phase)
0.8322	Intermediate Similarity	NPD4374	Clinical (unspecified phase)
0.831	Intermediate Similarity	NPD1683	Approved
0.8309	Intermediate Similarity	NPD3385	Approved
0.8284	Intermediate Similarity	NPD947	Approved
0.8264	Intermediate Similarity	NPD2172	Phase 1
0.8162	Intermediate Similarity	NPD1251	Discontinued
0.8148	Intermediate Similarity	NPD3654	Approved
0.8133	Intermediate Similarity	NPD3323	Discontinued
0.8058	Intermediate Similarity	NPD1254	Approved
0.8058	Intermediate Similarity	NPD1255	Approved
0.8058	Intermediate Similarity	NPD1253	Approved
0.8058	Intermediate Similarity	NPD1256	Approved
0.8027	Intermediate Similarity	NPD2837	Discontinued
0.7961	Intermediate Similarity	NPD5744	Clinical (unspecified phase)
0.7947	Intermediate Similarity	NPD972	Clinical (unspecified phase)
0.7902	Intermediate Similarity	NPD1592	Phase 3
0.7891	Intermediate Similarity	NPD3833	Phase 3
0.7891	Intermediate Similarity	NPD3835	Phase 3
0.7881	Intermediate Similarity	NPD1403	Approved
0.7881	Intermediate Similarity	NPD1404	Approved
0.7872	Intermediate Similarity	NPD6554	Approved
0.7872	Intermediate Similarity	NPD45	Approved
0.7857	Intermediate Similarity	NPD2641	Approved
0.7857	Intermediate Similarity	NPD2640	Approved
0.7806	Intermediate Similarity	NPD1325	Approved
0.7806	Intermediate Similarity	NPD1326	Approved
0.7762	Intermediate Similarity	NPD680	Discontinued
0.7756	Intermediate Similarity	NPD3610	Approved
0.7756	Intermediate Similarity	NPD3609	Approved
0.7755	Intermediate Similarity	NPD4547	Phase 3
0.7712	Intermediate Similarity	NPD1853	Clinical (unspecified phase)
0.7707	Intermediate Similarity	NPD4112	Clinical (unspecified phase)
0.7677	Intermediate Similarity	NPD2642	Approved
0.7677	Intermediate Similarity	NPD2639	Approved
0.7628	Intermediate Similarity	NPD5021	Discontinued
0.7628	Intermediate Similarity	NPD2185	Clinical (unspecified phase)
0.7628	Intermediate Similarity	NPD5069	Clinical (unspecified phase)
0.761	Intermediate Similarity	NPD4075	Phase 2
0.7562	Intermediate Similarity	NPD6203	Clinical (unspecified phase)
0.7562	Intermediate Similarity	NPD4181	Approved
0.7562	Intermediate Similarity	NPD3505	Approved
0.7562	Intermediate Similarity	NPD3506	Approved
0.7547	Intermediate Similarity	NPD4128	Approved
0.7516	Intermediate Similarity	NPD4076	Approved
0.7516	Intermediate Similarity	NPD4079	Approved
0.75	Intermediate Similarity	NPD1561	Phase 2
0.7485	Intermediate Similarity	NPD5105	Approved
0.7485	Intermediate Similarity	NPD5106	Approved
0.7483	Intermediate Similarity	NPD2006	Phase 2
0.7482	Intermediate Similarity	NPD2118	Approved
0.7482	Intermediate Similarity	NPD992	Clinical (unspecified phase)
0.7482	Intermediate Similarity	NPD2119	Approved
0.7482	Intermediate Similarity	NPD991	Phase 2
0.7469	Intermediate Similarity	NPD5473	Discontinued
0.7468	Intermediate Similarity	NPD4184	Clinical (unspecified phase)
0.7467	Intermediate Similarity	NPD2430	Phase 2
0.7451	Intermediate Similarity	NPD2150	Discontinued
0.7447	Intermediate Similarity	NPD3476	Approved
0.7447	Intermediate Similarity	NPD3475	Approved
0.7438	Intermediate Similarity	NPD5065	Approved
0.7432	Intermediate Similarity	NPD3401	Clinical (unspecified phase)
0.7432	Intermediate Similarity	NPD4509	Discontinued
0.7415	Intermediate Similarity	NPD3834	Clinical (unspecified phase)
0.7407	Intermediate Similarity	NPD8386	Phase 2
0.7405	Intermediate Similarity	NPD4779	Clinical (unspecified phase)
0.7394	Intermediate Similarity	NPD6610	Clinical (unspecified phase)
0.7365	Intermediate Similarity	NPD4047	Discontinued
0.7362	Intermediate Similarity	NPD702	Clinical (unspecified phase)
0.7362	Intermediate Similarity	NPD6277	Clinical (unspecified phase)
0.7362	Intermediate Similarity	NPD6595	Phase 3
0.7362	Intermediate Similarity	NPD8464	Clinical (unspecified phase)
0.7358	Intermediate Similarity	NPD5436	Phase 1
0.7346	Intermediate Similarity	NPD2144	Approved
0.7338	Intermediate Similarity	NPD2580	Discontinued
0.7333	Intermediate Similarity	NPD3607	Clinical (unspecified phase)
0.7317	Intermediate Similarity	NPD1708	Approved
0.7317	Intermediate Similarity	NPD1707	Approved
0.7317	Intermediate Similarity	NPD3038	Discontinued
0.7312	Intermediate Similarity	NPD6827	Clinical (unspecified phase)
0.7312	Intermediate Similarity	NPD6828	Phase 2
0.7305	Intermediate Similarity	NPD8431	Approved
0.7292	Intermediate Similarity	NPD4030	Approved
0.7292	Intermediate Similarity	NPD4029	Approved
0.7292	Intermediate Similarity	NPD4028	Approved
0.729	Intermediate Similarity	NPD4326	Phase 2
0.729	Intermediate Similarity	NPD1192	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD3318	Approved
0.7273	Intermediate Similarity	NPD1597	Phase 1
0.7273	Intermediate Similarity	NPD3319	Phase 1
0.7273	Intermediate Similarity	NPD3320	Approved
0.7266	Intermediate Similarity	NPD993	Approved
0.7266	Intermediate Similarity	NPD990	Approved
0.7261	Intermediate Similarity	NPD5315	Discontinued
0.7255	Intermediate Similarity	NPD2882	Phase 1
0.7248	Intermediate Similarity	NPD2007	Clinical (unspecified phase)
0.7246	Intermediate Similarity	NPD6217	Discontinued
0.7246	Intermediate Similarity	NPD4426	Clinical (unspecified phase)
0.7244	Intermediate Similarity	NPD1554	Clinical (unspecified phase)
0.7237	Intermediate Similarity	NPD5538	Clinical (unspecified phase)
0.7212	Intermediate Similarity	NPD1895	Discontinued
0.7202	Intermediate Similarity	NPD3961	Discontinued
0.7202	Intermediate Similarity	NPD3486	Clinical (unspecified phase)
0.7178	Intermediate Similarity	NPD749	Clinical (unspecified phase)
0.7176	Intermediate Similarity	NPD6630	Clinical (unspecified phase)
0.7163	Intermediate Similarity	NPD9583	Approved
0.716	Intermediate Similarity	NPD1534	Approved
0.716	Intermediate Similarity	NPD8110	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD6158	Phase 2
0.7143	Intermediate Similarity	NPD6476	Clinical (unspecified phase)
0.7125	Intermediate Similarity	NPD1248	Discontinued
0.7122	Intermediate Similarity	NPD5787	Discontinued
0.7117	Intermediate Similarity	NPD482	Approved
0.7115	Intermediate Similarity	NPD473	Clinical (unspecified phase)
0.7107	Intermediate Similarity	NPD5138	Approved
0.7107	Intermediate Similarity	NPD5140	Approved
0.7101	Intermediate Similarity	NPD5590	Clinical (unspecified phase)
0.7086	Intermediate Similarity	NPD1918	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD715	Phase 3
0.7081	Intermediate Similarity	NPD4638	Approved
0.7081	Intermediate Similarity	NPD4640	Approved
0.7081	Intermediate Similarity	NPD4639	Approved
0.707	Intermediate Similarity	NPD2330	Approved
0.707	Intermediate Similarity	NPD2865	Clinical (unspecified phase)
0.7066	Intermediate Similarity	NPD5728	Clinical (unspecified phase)
0.7066	Intermediate Similarity	NPD1332	Clinical (unspecified phase)
0.7063	Intermediate Similarity	NPD4550	Clinical (unspecified phase)
0.7055	Intermediate Similarity	NPD3944	Approved
0.7055	Intermediate Similarity	NPD3942	Approved
0.7051	Intermediate Similarity	NPD975	Approved
0.7051	Intermediate Similarity	NPD2165	Phase 1
0.7051	Intermediate Similarity	NPD977	Approved
0.7051	Intermediate Similarity	NPD976	Approved
0.705	Intermediate Similarity	NPD270	Clinical (unspecified phase)
0.705	Intermediate Similarity	NPD268	Approved
0.705	Intermediate Similarity	NPD271	Approved
0.7047	Intermediate Similarity	NPD768	Clinical (unspecified phase)
0.7044	Intermediate Similarity	NPD2385	Clinical (unspecified phase)
0.7021	Intermediate Similarity	NPD9357	Approved
0.7018	Intermediate Similarity	NPD5145	Clinical (unspecified phase)
0.7018	Intermediate Similarity	NPD4499	Approved
0.7012	Intermediate Similarity	NPD3799	Suspended
0.7011	Intermediate Similarity	NPD2960	Clinical (unspecified phase)
0.7006	Intermediate Similarity	NPD3112	Approved
0.7006	Intermediate Similarity	NPD3115	Approved
0.7006	Intermediate Similarity	NPD3113	Approved
0.7006	Intermediate Similarity	NPD3114	Approved
0.7	Intermediate Similarity	NPD2310	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD6141	Clinical (unspecified phase)
0.6988	Remote Similarity	NPD6448	Phase 1
0.6978	Remote Similarity	NPD4811	Discontinued
0.6977	Remote Similarity	NPD5913	Phase 3
0.6977	Remote Similarity	NPD5912	Clinical (unspecified phase)
0.6975	Remote Similarity	NPD2844	Phase 3
0.6957	Remote Similarity	NPD1313	Approved
0.6954	Remote Similarity	NPD3791	Clinical (unspecified phase)
0.6954	Remote Similarity	NPD5020	Approved
0.6946	Remote Similarity	NPD5962	Phase 2
0.6943	Remote Similarity	NPD6285	Phase 2
0.6933	Remote Similarity	NPD2069	Approved
0.6933	Remote Similarity	NPD2075	Approved
0.6933	Remote Similarity	NPD2073	Approved
0.6933	Remote Similarity	NPD2074	Approved
0.6933	Remote Similarity	NPD2072	Approved
0.6933	Remote Similarity	NPD2068	Approved
0.6933	Remote Similarity	NPD2071	Approved
0.6933	Remote Similarity	NPD2070	Approved
0.6928	Remote Similarity	NPD4398	Clinical (unspecified phase)
0.6928	Remote Similarity	NPD7111	Discontinued
0.6914	Remote Similarity	NPD2392	Clinical (unspecified phase)
0.6899	Remote Similarity	NPD2748	Clinical (unspecified phase)
0.6899	Remote Similarity	NPD2927	Phase 3
0.6897	Remote Similarity	NPD6451	Discontinued
0.689	Remote Similarity	NPD1567	Clinical (unspecified phase)
0.6886	Remote Similarity	NPD40	Phase 2
0.6886	Remote Similarity	NPD5730	Phase 2
0.6884	Remote Similarity	NPD9396	Approved
0.6884	Remote Similarity	NPD9392	Approved
0.6879	Remote Similarity	NPD6180	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD1598	Discontinued
0.6875	Remote Similarity	NPD5003	Discontinued
0.6875	Remote Similarity	NPD6664	Approved
0.6875	Remote Similarity	NPD6074	Clinical (unspecified phase)
0.6867	Remote Similarity	NPD6375	Clinical (unspecified phase)
0.6867	Remote Similarity	NPD5501	Discontinued
0.6864	Remote Similarity	NPD2095	Phase 2
0.6864	Remote Similarity	NPD2094	Phase 2
0.6864	Remote Similarity	NPD2092	Phase 2
0.6864	Remote Similarity	NPD3512	Clinical (unspecified phase)

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