NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	209.12
Volume:	237.505
LogP:	4.893
LogD:	4.281
LogS:	-6.213
# Rotatable Bonds:	2
TPSA:	15.79
# H-Bond Aceptor:	1
# H-Bond Donor:	1
# Rings:	3
# Heavy Atoms:	1

MedChem Properties

QED Drug-Likeness Score:	0.648
Synthetic Accessibility Score:	1.852
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:	-4.779
MDCK Permeability:	1.4518986063194461e-05
Pgp-inhibitor:	0.502
Pgp-substrate:	0.07
Human Intestinal Absorption (HIA):	0.003
20% Bioavailability (F20%):	0.96
30% Bioavailability (F30%):	0.966

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.672
Plasma Protein Binding (PPB):	96.90705108642578%
Volume Distribution (VD):	2.556
Pgp-substrate:	1.2814545631408691%

ADMET: Metabolism

CYP1A2-inhibitor:	0.992
CYP1A2-substrate:	0.643
CYP2C19-inhibitor:	0.83
CYP2C19-substrate:	0.164
CYP2C9-inhibitor:	0.648
CYP2C9-substrate:	0.88
CYP2D6-inhibitor:	0.854
CYP2D6-substrate:	0.886
CYP3A4-inhibitor:	0.549
CYP3A4-substrate:	0.231

ADMET: Excretion

Clearance (CL):	5.12
Half-life (T1/2):	0.232

ADMET: Toxicity

hERG Blockers:	0.028
Human Hepatotoxicity (H-HT):	0.156
Drug-inuced Liver Injury (DILI):	0.575
AMES Toxicity:	0.354
Rat Oral Acute Toxicity:	0.083
Maximum Recommended Daily Dose:	0.795
Skin Sensitization:	0.843
Carcinogencity:	0.662
Eye Corrosion:	0.141
Eye Irritation:	0.99
Respiratory Toxicity:	0.954

Download Data

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

Natural Product: NPC473587

Natural Product ID:	NPC473587
*Common Name:**	1-Propyl-9H-Carbazole
IUPAC Name:	1-propyl-9H-carbazole
Synonyms:
Standard InCHIKey:	NEKVNWJRLIKKJA-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C15H15N/c1-2-6-11-7-5-9-13-12-8-3-4-10-14(12)16-15(11)13/h3-5,7-10,16H,2,6H2,1H3
SMILES:	CCCc1cccc2c1[nH]c1c2cccc1
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL446537
PubChem CID:	18401421
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	=	25.0	ug.mL-1	PMID[515794]
NPT19	Organism	Escherichia coli	Escherichia coli	MIC	>	120.0	ug	PMID[515794]
NPT79	Organism	Bacillus subtilis	Bacillus subtilis	MIC	>	120.0	ug	PMID[515794]
NPT18	Organism	Pseudomonas aeruginosa	Pseudomonas aeruginosa	MIC	>	60.0	ug	PMID[515794]
NPT20	Organism	Candida albicans	Candida albicans	MIC	>	120.0	ug	PMID[515794]
NPT330	Organism	Trichophyton mentagrophytes	Trichophyton mentagrophytes	MIC	=	15.0	ug	PMID[515794]
NPT1223	Organism	Amorphotheca resinae	Amorphotheca resinae	MIC	>	120.0	ug	PMID[515794]

☑ 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 NPC473587 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	1167
0.1-0.2	12170
0.2-0.3	16877
0.3-0.4	7177
0.4-0.5	2329
0.5-0.6	1547
0.6-0.7	987
0.7-0.8	347
0.8-0.85	58
0.85-0.9	27
0.9-0.95	4
0.95-1	7

Similarity Score	Similarity Level	Natural Product ID
0.9919	High Similarity	NPC475428
0.9918	High Similarity	NPC473762
0.9839	High Similarity	NPC475450
0.9839	High Similarity	NPC179365
0.9754	High Similarity	NPC250361
0.9603	High Similarity	NPC473930
0.9426	High Similarity	NPC41174
0.9291	High Similarity	NPC22079
0.9167	High Similarity	NPC312092
0.9008	High Similarity	NPC198988
0.8939	High Similarity	NPC325252
0.8815	High Similarity	NPC115611
0.8797	High Similarity	NPC29886
0.8797	High Similarity	NPC261195
0.8731	High Similarity	NPC84911
0.8676	High Similarity	NPC2949
0.8676	High Similarity	NPC59084
0.8676	High Similarity	NPC284635
0.8672	High Similarity	NPC122718
0.8657	High Similarity	NPC96102
0.8657	High Similarity	NPC218268
0.8651	High Similarity	NPC215519
0.864	High Similarity	NPC54102
0.864	High Similarity	NPC162689
0.8629	High Similarity	NPC148140
0.8613	High Similarity	NPC63157
0.8613	High Similarity	NPC473868
0.8603	High Similarity	NPC88097
0.8603	High Similarity	NPC110126
0.8603	High Similarity	NPC73767
0.8593	High Similarity	NPC105127
0.8571	High Similarity	NPC477134
0.856	High Similarity	NPC81561
0.854	High Similarity	NPC469767
0.854	High Similarity	NPC469783
0.854	High Similarity	NPC469780
0.854	High Similarity	NPC469779
0.854	High Similarity	NPC469784
0.854	High Similarity	NPC469768
0.854	High Similarity	NPC469761
0.8511	High Similarity	NPC124005
0.85	High Similarity	NPC288838
0.8496	Intermediate Similarity	NPC82295
0.8489	Intermediate Similarity	NPC242556
0.8478	Intermediate Similarity	NPC469766
0.8456	Intermediate Similarity	NPC125746
0.8451	Intermediate Similarity	NPC33421
0.8451	Intermediate Similarity	NPC53947
0.844	Intermediate Similarity	NPC21605
0.844	Intermediate Similarity	NPC201380
0.844	Intermediate Similarity	NPC179787
0.8429	Intermediate Similarity	NPC470440
0.8417	Intermediate Similarity	NPC190296
0.8406	Intermediate Similarity	NPC279081
0.838	Intermediate Similarity	NPC321911
0.8369	Intermediate Similarity	NPC63545
0.8356	Intermediate Similarity	NPC474791
0.831	Intermediate Similarity	NPC469811
0.8299	Intermediate Similarity	NPC215584
0.8299	Intermediate Similarity	NPC44773
0.8298	Intermediate Similarity	NPC314372
0.8298	Intermediate Similarity	NPC204141
0.8288	Intermediate Similarity	NPC76982
0.8276	Intermediate Similarity	NPC38736
0.8273	Intermediate Similarity	NPC230002
0.8252	Intermediate Similarity	NPC37548
0.8252	Intermediate Similarity	NPC187951
0.8239	Intermediate Similarity	NPC129042
0.8239	Intermediate Similarity	NPC143872
0.8219	Intermediate Similarity	NPC184476
0.8207	Intermediate Similarity	NPC325903
0.8194	Intermediate Similarity	NPC148592
0.8182	Intermediate Similarity	NPC471957
0.8169	Intermediate Similarity	NPC159856
0.8163	Intermediate Similarity	NPC286427
0.8125	Intermediate Similarity	NPC2272
0.8108	Intermediate Similarity	NPC41257
0.8108	Intermediate Similarity	NPC474880
0.8108	Intermediate Similarity	NPC318065
0.8108	Intermediate Similarity	NPC221786
0.8108	Intermediate Similarity	NPC206819
0.8108	Intermediate Similarity	NPC56765
0.8108	Intermediate Similarity	NPC475990
0.8069	Intermediate Similarity	NPC105818
0.8069	Intermediate Similarity	NPC24678
0.8054	Intermediate Similarity	NPC473320
0.8054	Intermediate Similarity	NPC229173
0.8041	Intermediate Similarity	NPC236711
0.8041	Intermediate Similarity	NPC216643
0.8027	Intermediate Similarity	NPC471458
0.8027	Intermediate Similarity	NPC470507
0.8014	Intermediate Similarity	NPC470823
0.8014	Intermediate Similarity	NPC470233
0.8	Intermediate Similarity	NPC16667
0.7987	Intermediate Similarity	NPC135141
0.7987	Intermediate Similarity	NPC92796
0.7973	Intermediate Similarity	NPC285469
0.7959	Intermediate Similarity	NPC469765
0.7959	Intermediate Similarity	NPC200214
0.7959	Intermediate Similarity	NPC469763
0.7959	Intermediate Similarity	NPC73952
0.7959	Intermediate Similarity	NPC25008
0.7959	Intermediate Similarity	NPC469786
0.7959	Intermediate Similarity	NPC469760
0.7959	Intermediate Similarity	NPC259644
0.7959	Intermediate Similarity	NPC141926
0.7947	Intermediate Similarity	NPC162799
0.7947	Intermediate Similarity	NPC271734
0.7947	Intermediate Similarity	NPC90723
0.7919	Intermediate Similarity	NPC299594
0.7905	Intermediate Similarity	NPC80597
0.7905	Intermediate Similarity	NPC212376
0.7905	Intermediate Similarity	NPC75540
0.7905	Intermediate Similarity	NPC34844
0.7905	Intermediate Similarity	NPC70922
0.7905	Intermediate Similarity	NPC207726
0.7905	Intermediate Similarity	NPC211572
0.7891	Intermediate Similarity	NPC216713
0.7872	Intermediate Similarity	NPC169433
0.7852	Intermediate Similarity	NPC141353
0.7852	Intermediate Similarity	NPC476140
0.7838	Intermediate Similarity	NPC161108
0.7829	Intermediate Similarity	NPC317105
0.7817	Intermediate Similarity	NPC104483
0.7815	Intermediate Similarity	NPC122141
0.7815	Intermediate Similarity	NPC470204
0.7801	Intermediate Similarity	NPC314102
0.7801	Intermediate Similarity	NPC150259
0.7801	Intermediate Similarity	NPC251722
0.7792	Intermediate Similarity	NPC201700
0.7792	Intermediate Similarity	NPC154293
0.7785	Intermediate Similarity	NPC476219
0.7785	Intermediate Similarity	NPC476297
0.7778	Intermediate Similarity	NPC115232
0.7763	Intermediate Similarity	NPC282231
0.7763	Intermediate Similarity	NPC470203
0.7761	Intermediate Similarity	NPC46358
0.7748	Intermediate Similarity	NPC67056
0.7742	Intermediate Similarity	NPC474897
0.7742	Intermediate Similarity	NPC280548
0.7742	Intermediate Similarity	NPC194411
0.774	Intermediate Similarity	NPC316069
0.7733	Intermediate Similarity	NPC469785
0.7718	Intermediate Similarity	NPC232798
0.7712	Intermediate Similarity	NPC472587
0.7712	Intermediate Similarity	NPC21174
0.7712	Intermediate Similarity	NPC271797
0.7712	Intermediate Similarity	NPC8104
0.7697	Intermediate Similarity	NPC279918
0.7692	Intermediate Similarity	NPC6982
0.7687	Intermediate Similarity	NPC114209
0.7682	Intermediate Similarity	NPC469762
0.7677	Intermediate Similarity	NPC63751
0.7673	Intermediate Similarity	NPC88363
0.7662	Intermediate Similarity	NPC274229
0.7655	Intermediate Similarity	NPC20144
0.7647	Intermediate Similarity	NPC214106
0.7643	Intermediate Similarity	NPC97525
0.7643	Intermediate Similarity	NPC34508
0.7632	Intermediate Similarity	NPC230869
0.7619	Intermediate Similarity	NPC478186
0.7619	Intermediate Similarity	NPC302790
0.7613	Intermediate Similarity	NPC49954
0.7613	Intermediate Similarity	NPC474561
0.7597	Intermediate Similarity	NPC311276
0.7597	Intermediate Similarity	NPC247987
0.7597	Intermediate Similarity	NPC194640
0.7597	Intermediate Similarity	NPC40779
0.7595	Intermediate Similarity	NPC329688
0.7595	Intermediate Similarity	NPC275305
0.7595	Intermediate Similarity	NPC37423
0.7595	Intermediate Similarity	NPC189812
0.7582	Intermediate Similarity	NPC131718
0.758	Intermediate Similarity	NPC82331
0.7568	Intermediate Similarity	NPC470111
0.7548	Intermediate Similarity	NPC280864
0.7548	Intermediate Similarity	NPC470508
0.7548	Intermediate Similarity	NPC17751
0.7547	Intermediate Similarity	NPC288785
0.7547	Intermediate Similarity	NPC280852
0.7532	Intermediate Similarity	NPC477611
0.7532	Intermediate Similarity	NPC474409
0.7531	Intermediate Similarity	NPC212535
0.7517	Intermediate Similarity	NPC238499
0.7516	Intermediate Similarity	NPC97343
0.75	Intermediate Similarity	NPC151939
0.75	Intermediate Similarity	NPC68354
0.75	Intermediate Similarity	NPC109447
0.75	Intermediate Similarity	NPC54988
0.75	Intermediate Similarity	NPC49217
0.75	Intermediate Similarity	NPC470509
0.75	Intermediate Similarity	NPC160105
0.7485	Intermediate Similarity	NPC190007
0.7484	Intermediate Similarity	NPC102423
0.7484	Intermediate Similarity	NPC149265
0.7483	Intermediate Similarity	NPC200743
0.7468	Intermediate Similarity	NPC470498
0.7467	Intermediate Similarity	NPC40070
0.7466	Intermediate Similarity	NPC277157
0.7453	Intermediate Similarity	NPC270009

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 NPC473587 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	524
0.1-0.2	818
0.2-0.3	1029
0.3-0.4	2155
0.4-0.5	2388
0.5-0.6	1578
0.6-0.7	537
0.7-0.8	99
0.8-0.85	15
0.85-0.9	6
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9037	High Similarity	NPD5254	Discontinued
0.9015	High Similarity	NPD1262	Discovery
0.8955	High Similarity	NPD3943	Clinical (unspecified phase)
0.8657	High Similarity	NPD198	Clinical (unspecified phase)
0.8603	High Similarity	NPD786	Approved
0.8511	High Similarity	NPD3100	Discontinued
0.85	High Similarity	NPD1528	Clinical (unspecified phase)
0.8478	Intermediate Similarity	NPD1722	Approved
0.8451	Intermediate Similarity	NPD4463	Approved
0.8451	Intermediate Similarity	NPD4462	Approved
0.8444	Intermediate Similarity	NPD4880	Discontinued
0.8417	Intermediate Similarity	NPD4637	Clinical (unspecified phase)
0.838	Intermediate Similarity	NPD4374	Clinical (unspecified phase)
0.837	Intermediate Similarity	NPD3385	Approved
0.8369	Intermediate Similarity	NPD1683	Approved
0.8346	Intermediate Similarity	NPD947	Approved
0.8322	Intermediate Similarity	NPD2172	Phase 1
0.8209	Intermediate Similarity	NPD3654	Approved
0.8116	Intermediate Similarity	NPD1253	Approved
0.8116	Intermediate Similarity	NPD1256	Approved
0.8116	Intermediate Similarity	NPD1254	Approved
0.8116	Intermediate Similarity	NPD1255	Approved
0.8088	Intermediate Similarity	NPD1251	Discontinued
0.8082	Intermediate Similarity	NPD2837	Discontinued
0.8067	Intermediate Similarity	NPD3323	Discontinued
0.7958	Intermediate Similarity	NPD1592	Phase 3
0.7945	Intermediate Similarity	NPD3833	Phase 3
0.7945	Intermediate Similarity	NPD3835	Phase 3
0.7933	Intermediate Similarity	NPD1404	Approved
0.7933	Intermediate Similarity	NPD1403	Approved
0.7929	Intermediate Similarity	NPD6554	Approved
0.7929	Intermediate Similarity	NPD45	Approved
0.7895	Intermediate Similarity	NPD5744	Clinical (unspecified phase)
0.7881	Intermediate Similarity	NPD972	Clinical (unspecified phase)
0.7857	Intermediate Similarity	NPD1326	Approved
0.7857	Intermediate Similarity	NPD1325	Approved
0.7817	Intermediate Similarity	NPD680	Discontinued
0.7808	Intermediate Similarity	NPD4547	Phase 3
0.7792	Intermediate Similarity	NPD2641	Approved
0.7792	Intermediate Similarity	NPD2640	Approved
0.7763	Intermediate Similarity	NPD1853	Clinical (unspecified phase)
0.7727	Intermediate Similarity	NPD2639	Approved
0.7727	Intermediate Similarity	NPD2642	Approved
0.7692	Intermediate Similarity	NPD3609	Approved
0.7692	Intermediate Similarity	NPD3610	Approved
0.7677	Intermediate Similarity	NPD5069	Clinical (unspecified phase)
0.7677	Intermediate Similarity	NPD2185	Clinical (unspecified phase)
0.7677	Intermediate Similarity	NPD5021	Discontinued
0.7643	Intermediate Similarity	NPD4112	Clinical (unspecified phase)
0.761	Intermediate Similarity	NPD6203	Clinical (unspecified phase)
0.7595	Intermediate Similarity	NPD4128	Approved
0.7556	Intermediate Similarity	NPD1561	Phase 2
0.7547	Intermediate Similarity	NPD4075	Phase 2
0.7536	Intermediate Similarity	NPD991	Phase 2
0.7536	Intermediate Similarity	NPD992	Clinical (unspecified phase)
0.7534	Intermediate Similarity	NPD2006	Phase 2
0.7531	Intermediate Similarity	NPD5105	Approved
0.7531	Intermediate Similarity	NPD5106	Approved
0.7517	Intermediate Similarity	NPD2430	Phase 2
0.75	Intermediate Similarity	NPD3506	Approved
0.75	Intermediate Similarity	NPD3476	Approved
0.75	Intermediate Similarity	NPD3475	Approved
0.75	Intermediate Similarity	NPD2150	Discontinued
0.75	Intermediate Similarity	NPD3505	Approved
0.75	Intermediate Similarity	NPD4181	Approved
0.7484	Intermediate Similarity	NPD5065	Approved
0.7483	Intermediate Similarity	NPD3401	Clinical (unspecified phase)
0.7483	Intermediate Similarity	NPD4509	Discontinued
0.7466	Intermediate Similarity	NPD3834	Clinical (unspecified phase)
0.7453	Intermediate Similarity	NPD4079	Approved
0.7453	Intermediate Similarity	NPD8386	Phase 2
0.7453	Intermediate Similarity	NPD4076	Approved
0.7439	Intermediate Similarity	NPD6610	Clinical (unspecified phase)
0.7415	Intermediate Similarity	NPD4047	Discontinued
0.741	Intermediate Similarity	NPD2119	Approved
0.741	Intermediate Similarity	NPD2118	Approved
0.7407	Intermediate Similarity	NPD6595	Phase 3
0.7407	Intermediate Similarity	NPD702	Clinical (unspecified phase)
0.7407	Intermediate Similarity	NPD8464	Clinical (unspecified phase)
0.7407	Intermediate Similarity	NPD5473	Discontinued
0.7405	Intermediate Similarity	NPD4184	Clinical (unspecified phase)
0.7405	Intermediate Similarity	NPD5436	Phase 1
0.7391	Intermediate Similarity	NPD2144	Approved
0.7386	Intermediate Similarity	NPD2580	Discontinued
0.7378	Intermediate Similarity	NPD3607	Clinical (unspecified phase)
0.7362	Intermediate Similarity	NPD1708	Approved
0.7362	Intermediate Similarity	NPD1707	Approved
0.7358	Intermediate Similarity	NPD6827	Clinical (unspecified phase)
0.7358	Intermediate Similarity	NPD6828	Phase 2
0.7349	Intermediate Similarity	NPD8431	Approved
0.7342	Intermediate Similarity	NPD4779	Clinical (unspecified phase)
0.7338	Intermediate Similarity	NPD1192	Clinical (unspecified phase)
0.7338	Intermediate Similarity	NPD4326	Phase 2
0.7323	Intermediate Similarity	NPD993	Approved
0.7323	Intermediate Similarity	NPD990	Approved
0.732	Intermediate Similarity	NPD1597	Phase 1
0.7317	Intermediate Similarity	NPD3320	Approved
0.7317	Intermediate Similarity	NPD3319	Phase 1
0.7317	Intermediate Similarity	NPD3318	Approved
0.7303	Intermediate Similarity	NPD2882	Phase 1
0.7301	Intermediate Similarity	NPD6277	Clinical (unspecified phase)
0.729	Intermediate Similarity	NPD1554	Clinical (unspecified phase)
0.7285	Intermediate Similarity	NPD5538	Clinical (unspecified phase)
0.7256	Intermediate Similarity	NPD3038	Discontinued
0.7256	Intermediate Similarity	NPD1895	Discontinued
0.7222	Intermediate Similarity	NPD4029	Approved
0.7222	Intermediate Similarity	NPD4030	Approved
0.7222	Intermediate Similarity	NPD749	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD4028	Approved
0.7214	Intermediate Similarity	NPD9583	Approved
0.7197	Intermediate Similarity	NPD5315	Discontinued
0.719	Intermediate Similarity	NPD6476	Clinical (unspecified phase)
0.719	Intermediate Similarity	NPD6158	Phase 2
0.7186	Intermediate Similarity	NPD6217	Discontinued
0.7186	Intermediate Similarity	NPD4426	Clinical (unspecified phase)
0.7181	Intermediate Similarity	NPD2007	Clinical (unspecified phase)
0.7174	Intermediate Similarity	NPD5787	Discontinued
0.717	Intermediate Similarity	NPD1248	Discontinued
0.7161	Intermediate Similarity	NPD473	Clinical (unspecified phase)
0.716	Intermediate Similarity	NPD482	Approved
0.7152	Intermediate Similarity	NPD5138	Approved
0.7152	Intermediate Similarity	NPD5140	Approved
0.7143	Intermediate Similarity	NPD3486	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD5590	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD3961	Discontinued
0.7133	Intermediate Similarity	NPD715	Phase 3
0.7133	Intermediate Similarity	NPD1918	Clinical (unspecified phase)
0.7118	Intermediate Similarity	NPD6630	Clinical (unspecified phase)
0.7115	Intermediate Similarity	NPD2330	Approved
0.7115	Intermediate Similarity	NPD2865	Clinical (unspecified phase)
0.7108	Intermediate Similarity	NPD1332	Clinical (unspecified phase)
0.7107	Intermediate Similarity	NPD4550	Clinical (unspecified phase)
0.7103	Intermediate Similarity	NPD3944	Approved
0.7103	Intermediate Similarity	NPD3942	Approved
0.7101	Intermediate Similarity	NPD270	Clinical (unspecified phase)
0.7101	Intermediate Similarity	NPD271	Approved
0.7101	Intermediate Similarity	NPD268	Approved
0.7101	Intermediate Similarity	NPD1534	Approved
0.7101	Intermediate Similarity	NPD8110	Clinical (unspecified phase)
0.7097	Intermediate Similarity	NPD2165	Phase 1
0.7089	Intermediate Similarity	NPD2385	Clinical (unspecified phase)
0.7071	Intermediate Similarity	NPD9357	Approved
0.7059	Intermediate Similarity	NPD5145	Clinical (unspecified phase)
0.7055	Intermediate Similarity	NPD3799	Suspended
0.7051	Intermediate Similarity	NPD3113	Approved
0.7051	Intermediate Similarity	NPD3115	Approved
0.7051	Intermediate Similarity	NPD3114	Approved
0.7051	Intermediate Similarity	NPD3112	Approved
0.7041	Intermediate Similarity	NPD2310	Clinical (unspecified phase)
0.7041	Intermediate Similarity	NPD6141	Clinical (unspecified phase)
0.703	Intermediate Similarity	NPD6448	Phase 1
0.7029	Intermediate Similarity	NPD4811	Discontinued
0.7019	Intermediate Similarity	NPD4638	Approved
0.7019	Intermediate Similarity	NPD2844	Phase 3
0.7019	Intermediate Similarity	NPD4639	Approved
0.7019	Intermediate Similarity	NPD4640	Approved
0.7018	Intermediate Similarity	NPD5912	Clinical (unspecified phase)
0.7018	Intermediate Similarity	NPD5913	Phase 3
0.7006	Intermediate Similarity	NPD5728	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD5020	Approved
0.6994	Remote Similarity	NPD3791	Clinical (unspecified phase)
0.6988	Remote Similarity	NPD5962	Phase 2
0.6987	Remote Similarity	NPD976	Approved
0.6987	Remote Similarity	NPD977	Approved
0.6987	Remote Similarity	NPD6285	Phase 2
0.6987	Remote Similarity	NPD975	Approved
0.698	Remote Similarity	NPD768	Clinical (unspecified phase)
0.697	Remote Similarity	NPD4398	Clinical (unspecified phase)
0.6959	Remote Similarity	NPD4499	Approved
0.6957	Remote Similarity	NPD2392	Clinical (unspecified phase)
0.6954	Remote Similarity	NPD2960	Clinical (unspecified phase)
0.6943	Remote Similarity	NPD2927	Phase 3
0.6943	Remote Similarity	NPD2748	Clinical (unspecified phase)
0.6934	Remote Similarity	NPD9396	Approved
0.6934	Remote Similarity	NPD9392	Approved
0.6933	Remote Similarity	NPD1567	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD1598	Discontinued
0.6919	Remote Similarity	NPD6180	Clinical (unspecified phase)
0.6918	Remote Similarity	NPD6074	Clinical (unspecified phase)
0.6912	Remote Similarity	NPD269	Clinical (unspecified phase)
0.6905	Remote Similarity	NPD2095	Phase 2
0.6905	Remote Similarity	NPD2094	Phase 2
0.6905	Remote Similarity	NPD2092	Phase 2
0.6899	Remote Similarity	NPD1648	Phase 1
0.6899	Remote Similarity	NPD1647	Phase 1
0.6897	Remote Similarity	NPD7618	Phase 3
0.6897	Remote Similarity	NPD7619	Phase 3
0.6894	Remote Similarity	NPD509	Phase 3
0.6894	Remote Similarity	NPD1313	Approved
0.6894	Remote Similarity	NPD2915	Discontinued
0.6894	Remote Similarity	NPD2720	Phase 1
0.6894	Remote Similarity	NPD2719	Clinical (unspecified phase)
0.689	Remote Similarity	NPD750	Phase 2
0.6867	Remote Similarity	NPD2074	Approved
0.6867	Remote Similarity	NPD2071	Approved
0.6867	Remote Similarity	NPD2072	Approved
0.6867	Remote Similarity	NPD2069	Approved
0.6867	Remote Similarity	NPD2070	Approved
0.6867	Remote Similarity	NPD7111	Discontinued
0.6867	Remote Similarity	NPD2075	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