NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	243.1
Volume:	272.927
LogP:	5.141
LogD:	4.314
LogS:	-6.413
# Rotatable Bonds:	1
TPSA:	15.79
# H-Bond Aceptor:	1
# H-Bond Donor:	1
# Rings:	4
# Heavy Atoms:	1

MedChem Properties

QED Drug-Likeness Score:	0.485
Synthetic Accessibility Score:	1.682
Fsp3:	0.0
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:	-4.879
MDCK Permeability:	1.5077835996635258e-05
Pgp-inhibitor:	0.055
Pgp-substrate:	0.743
Human Intestinal Absorption (HIA):	0.005
20% Bioavailability (F20%):	0.999
30% Bioavailability (F30%):	0.917

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.508
Plasma Protein Binding (PPB):	98.65532684326172%
Volume Distribution (VD):	1.065
Pgp-substrate:	0.8408879637718201%

ADMET: Metabolism

CYP1A2-inhibitor:	0.995
CYP1A2-substrate:	0.284
CYP2C19-inhibitor:	0.768
CYP2C19-substrate:	0.063
CYP2C9-inhibitor:	0.6
CYP2C9-substrate:	0.819
CYP2D6-inhibitor:	0.661
CYP2D6-substrate:	0.85
CYP3A4-inhibitor:	0.439
CYP3A4-substrate:	0.216

ADMET: Excretion

Clearance (CL):	4.973
Half-life (T1/2):	0.119

ADMET: Toxicity

hERG Blockers:	0.061
Human Hepatotoxicity (H-HT):	0.114
Drug-inuced Liver Injury (DILI):	0.845
AMES Toxicity:	0.772
Rat Oral Acute Toxicity:	0.069
Maximum Recommended Daily Dose:	0.738
Skin Sensitization:	0.87
Carcinogencity:	0.778
Eye Corrosion:	0.018
Eye Irritation:	0.986
Respiratory Toxicity:	0.923

Download Data

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

Natural Product: NPC473930

Natural Product ID:	NPC473930
*Common Name:**	1-Phenyl-9H-Carbazole
IUPAC Name:	1-phenyl-9H-carbazole
Synonyms:
Standard InCHIKey:	FBTOLQFRGURPJH-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C18H13N/c1-2-7-13(8-3-1)14-10-6-11-16-15-9-4-5-12-17(15)19-18(14)16/h1-12,19H
SMILES:	C1=CC=C(C=C1)C2=CC=CC3=C2NC4=CC=CC=C34
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL455562
PubChem CID:	13497474
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
Others	1

Activity Type	# Activity
Cell Line	1
Individual Protein	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	=	90.0	ug.mL-1	PMID[492379]
NPT19	Organism	Escherichia coli	Escherichia coli	MIC	>	60.0	ug	PMID[492379]
NPT79	Organism	Bacillus subtilis	Bacillus subtilis	MIC	>	60.0	ug	PMID[492379]
NPT18	Organism	Pseudomonas aeruginosa	Pseudomonas aeruginosa	MIC	>	60.0	ug	PMID[492379]
NPT20	Organism	Candida albicans	Candida albicans	MIC	>	60.0	ug	PMID[492379]
NPT330	Organism	Trichophyton mentagrophytes	Trichophyton mentagrophytes	MIC	>	60.0	ug	PMID[492379]
NPT1223	Organism	Amorphotheca resinae	Amorphotheca resinae	MIC	>	60.0	ug	PMID[492379]
NPT832	Individual Protein	Kinesin-like protein 1	Homo sapiens	Inhibition	<	50.0	%	PMID[492380]

☑ 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 NPC473930 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	1405
0.1-0.2	13632
0.2-0.3	16547
0.3-0.4	6115
0.4-0.5	2203
0.5-0.6	1477
0.6-0.7	965
0.7-0.8	275
0.8-0.85	54
0.85-0.9	14
0.9-0.95	2
0.95-1	8

Similarity Score	Similarity Level	Natural Product ID
0.968	High Similarity	NPC473762
0.9606	High Similarity	NPC475450
0.9603	High Similarity	NPC473587
0.9542	High Similarity	NPC312092
0.9528	High Similarity	NPC475428
0.952	High Similarity	NPC250361
0.9453	High Similarity	NPC179365
0.9048	High Similarity	NPC41174
0.8931	High Similarity	NPC22079
0.8759	High Similarity	NPC284635
0.8667	High Similarity	NPC198988
0.8652	High Similarity	NPC477134
0.8615	High Similarity	NPC122718
0.8603	High Similarity	NPC325252
0.8583	High Similarity	NPC162689
0.8583	High Similarity	NPC54102
0.8582	High Similarity	NPC288838
0.8551	High Similarity	NPC88097
0.8489	Intermediate Similarity	NPC59084
0.8489	Intermediate Similarity	NPC2949
0.8489	Intermediate Similarity	NPC115611
0.8467	Intermediate Similarity	NPC29886
0.8467	Intermediate Similarity	NPC96102
0.8467	Intermediate Similarity	NPC218268
0.8467	Intermediate Similarity	NPC261195
0.8429	Intermediate Similarity	NPC63157
0.8429	Intermediate Similarity	NPC473868
0.8414	Intermediate Similarity	NPC325903
0.8406	Intermediate Similarity	NPC84911
0.8406	Intermediate Similarity	NPC105127
0.8403	Intermediate Similarity	NPC33421
0.8403	Intermediate Similarity	NPC53947
0.8392	Intermediate Similarity	NPC21605
0.8378	Intermediate Similarity	NPC44773
0.8378	Intermediate Similarity	NPC215584
0.8367	Intermediate Similarity	NPC216643
0.8357	Intermediate Similarity	NPC469783
0.8357	Intermediate Similarity	NPC469784
0.8357	Intermediate Similarity	NPC469761
0.8357	Intermediate Similarity	NPC469779
0.8357	Intermediate Similarity	NPC469780
0.8357	Intermediate Similarity	NPC469767
0.8357	Intermediate Similarity	NPC469768
0.8333	Intermediate Similarity	NPC124005
0.831	Intermediate Similarity	NPC242556
0.8309	Intermediate Similarity	NPC82295
0.8308	Intermediate Similarity	NPC215519
0.8298	Intermediate Similarity	NPC469766
0.8286	Intermediate Similarity	NPC110126
0.8286	Intermediate Similarity	NPC73767
0.8281	Intermediate Similarity	NPC148140
0.8273	Intermediate Similarity	NPC125746
0.8227	Intermediate Similarity	NPC279081
0.8217	Intermediate Similarity	NPC81561
0.8194	Intermediate Similarity	NPC63545
0.8188	Intermediate Similarity	NPC41257
0.8138	Intermediate Similarity	NPC469811
0.8138	Intermediate Similarity	NPC179787
0.8138	Intermediate Similarity	NPC201380
0.8133	Intermediate Similarity	NPC229173
0.8125	Intermediate Similarity	NPC204141
0.8125	Intermediate Similarity	NPC470440
0.8121	Intermediate Similarity	NPC76982
0.8121	Intermediate Similarity	NPC286427
0.8112	Intermediate Similarity	NPC190296
0.8108	Intermediate Similarity	NPC38736
0.8099	Intermediate Similarity	NPC230002
0.8082	Intermediate Similarity	NPC187951
0.8082	Intermediate Similarity	NPC37548
0.8082	Intermediate Similarity	NPC321911
0.8069	Intermediate Similarity	NPC129042
0.8069	Intermediate Similarity	NPC143872
0.8067	Intermediate Similarity	NPC206819
0.8067	Intermediate Similarity	NPC135141
0.8067	Intermediate Similarity	NPC474880
0.8067	Intermediate Similarity	NPC318065
0.8067	Intermediate Similarity	NPC56765
0.8067	Intermediate Similarity	NPC475990
0.8067	Intermediate Similarity	NPC221786
0.8067	Intermediate Similarity	NPC474791
0.8067	Intermediate Similarity	NPC92796
0.8054	Intermediate Similarity	NPC184476
0.8026	Intermediate Similarity	NPC317105
0.8	Intermediate Similarity	NPC159856
0.8	Intermediate Similarity	NPC314372
0.7973	Intermediate Similarity	NPC470233
0.7959	Intermediate Similarity	NPC2272
0.7908	Intermediate Similarity	NPC162799
0.7905	Intermediate Similarity	NPC148592
0.7905	Intermediate Similarity	NPC24678
0.7905	Intermediate Similarity	NPC105818
0.7895	Intermediate Similarity	NPC473320
0.7891	Intermediate Similarity	NPC471957
0.7867	Intermediate Similarity	NPC471458
0.7867	Intermediate Similarity	NPC470507
0.7843	Intermediate Similarity	NPC16667
0.7832	Intermediate Similarity	NPC169433
0.7821	Intermediate Similarity	NPC474897
0.7815	Intermediate Similarity	NPC285469
0.78	Intermediate Similarity	NPC73952
0.78	Intermediate Similarity	NPC469765
0.78	Intermediate Similarity	NPC469760
0.78	Intermediate Similarity	NPC259644
0.78	Intermediate Similarity	NPC469763
0.78	Intermediate Similarity	NPC469786
0.78	Intermediate Similarity	NPC25008
0.7792	Intermediate Similarity	NPC90723
0.7792	Intermediate Similarity	NPC271734
0.7778	Intermediate Similarity	NPC122141
0.7763	Intermediate Similarity	NPC299594
0.7763	Intermediate Similarity	NPC236711
0.7762	Intermediate Similarity	NPC251722
0.7762	Intermediate Similarity	NPC314102
0.7756	Intermediate Similarity	NPC63751
0.7756	Intermediate Similarity	NPC154293
0.7748	Intermediate Similarity	NPC476219
0.7748	Intermediate Similarity	NPC80597
0.7748	Intermediate Similarity	NPC211572
0.7748	Intermediate Similarity	NPC70922
0.7748	Intermediate Similarity	NPC212376
0.7748	Intermediate Similarity	NPC75540
0.7748	Intermediate Similarity	NPC207726
0.7733	Intermediate Similarity	NPC216713
0.7733	Intermediate Similarity	NPC470823
0.7727	Intermediate Similarity	NPC470203
0.7722	Intermediate Similarity	NPC97525
0.7707	Intermediate Similarity	NPC194411
0.7697	Intermediate Similarity	NPC141353
0.7697	Intermediate Similarity	NPC469785
0.7682	Intermediate Similarity	NPC141926
0.7682	Intermediate Similarity	NPC200214
0.7677	Intermediate Similarity	NPC21174
0.7677	Intermediate Similarity	NPC271797
0.7677	Intermediate Similarity	NPC8104
0.7662	Intermediate Similarity	NPC470204
0.7655	Intermediate Similarity	NPC104483
0.7647	Intermediate Similarity	NPC469762
0.7643	Intermediate Similarity	NPC201700
0.7639	Intermediate Similarity	NPC150259
0.7632	Intermediate Similarity	NPC34844
0.7632	Intermediate Similarity	NPC476297
0.7625	Intermediate Similarity	NPC280852
0.7622	Intermediate Similarity	NPC473189
0.7619	Intermediate Similarity	NPC20144
0.761	Intermediate Similarity	NPC477611
0.7597	Intermediate Similarity	NPC67056
0.7595	Intermediate Similarity	NPC280548
0.7591	Intermediate Similarity	NPC46358
0.7584	Intermediate Similarity	NPC316069
0.7578	Intermediate Similarity	NPC59269
0.7578	Intermediate Similarity	NPC302790
0.7566	Intermediate Similarity	NPC200743
0.7566	Intermediate Similarity	NPC161108
0.7566	Intermediate Similarity	NPC232798
0.7564	Intermediate Similarity	NPC472587
0.7562	Intermediate Similarity	NPC275305
0.7562	Intermediate Similarity	NPC329688
0.7562	Intermediate Similarity	NPC189812
0.7562	Intermediate Similarity	NPC37423
0.7554	Intermediate Similarity	NPC476140
0.7548	Intermediate Similarity	NPC279918
0.7547	Intermediate Similarity	NPC6982
0.7533	Intermediate Similarity	NPC114209
0.7532	Intermediate Similarity	NPC317430
0.7531	Intermediate Similarity	NPC6093
0.7516	Intermediate Similarity	NPC274229
0.7516	Intermediate Similarity	NPC115232
0.75	Intermediate Similarity	NPC117027
0.75	Intermediate Similarity	NPC282231
0.75	Intermediate Similarity	NPC34508
0.7485	Intermediate Similarity	NPC198339
0.7485	Intermediate Similarity	NPC300688
0.7484	Intermediate Similarity	NPC471943
0.7484	Intermediate Similarity	NPC230869
0.7469	Intermediate Similarity	NPC151939
0.7469	Intermediate Similarity	NPC68354
0.7468	Intermediate Similarity	NPC49954
0.7468	Intermediate Similarity	NPC474561
0.7467	Intermediate Similarity	NPC478186
0.7452	Intermediate Similarity	NPC40779
0.7452	Intermediate Similarity	NPC247987
0.7452	Intermediate Similarity	NPC311276
0.7452	Intermediate Similarity	NPC194640
0.7439	Intermediate Similarity	NPC302191
0.7436	Intermediate Similarity	NPC131718
0.7434	Intermediate Similarity	NPC40070
0.7423	Intermediate Similarity	NPC88363
0.7423	Intermediate Similarity	NPC176199
0.7423	Intermediate Similarity	NPC215795
0.7407	Intermediate Similarity	NPC288785
0.7405	Intermediate Similarity	NPC17751
0.7405	Intermediate Similarity	NPC470508
0.7405	Intermediate Similarity	NPC280864
0.7391	Intermediate Similarity	NPC474409
0.7391	Intermediate Similarity	NPC472123
0.7391	Intermediate Similarity	NPC252572
0.7391	Intermediate Similarity	NPC161861
0.7389	Intermediate Similarity	NPC214106
0.7378	Intermediate Similarity	NPC314919
0.7378	Intermediate Similarity	NPC88110

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 NPC473930 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	599
0.1-0.2	868
0.2-0.3	1063
0.3-0.4	2245
0.4-0.5	2334
0.5-0.6	1497
0.6-0.7	450
0.7-0.8	75
0.8-0.85	13
0.85-0.9	6
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8841	High Similarity	NPD5254	Discontinued
0.8815	High Similarity	NPD1262	Discovery
0.8759	High Similarity	NPD3943	Clinical (unspecified phase)
0.8667	High Similarity	NPD4880	Discontinued
0.8467	Intermediate Similarity	NPD198	Clinical (unspecified phase)
0.8462	Intermediate Similarity	NPD4374	Clinical (unspecified phase)
0.8451	Intermediate Similarity	NPD1528	Clinical (unspecified phase)
0.8369	Intermediate Similarity	NPD4637	Clinical (unspecified phase)
0.8333	Intermediate Similarity	NPD3100	Discontinued
0.8321	Intermediate Similarity	NPD3385	Approved
0.8298	Intermediate Similarity	NPD1722	Approved
0.8296	Intermediate Similarity	NPD947	Approved
0.8286	Intermediate Similarity	NPD786	Approved
0.8276	Intermediate Similarity	NPD4462	Approved
0.8276	Intermediate Similarity	NPD4463	Approved
0.8194	Intermediate Similarity	NPD1683	Approved
0.8163	Intermediate Similarity	NPD2837	Discontinued
0.8151	Intermediate Similarity	NPD2172	Phase 1
0.8146	Intermediate Similarity	NPD3323	Discontinued
0.8043	Intermediate Similarity	NPD1251	Discontinued
0.8029	Intermediate Similarity	NPD3654	Approved
0.8014	Intermediate Similarity	NPD45	Approved
0.8014	Intermediate Similarity	NPD6554	Approved
0.7961	Intermediate Similarity	NPD1853	Clinical (unspecified phase)
0.7943	Intermediate Similarity	NPD1256	Approved
0.7943	Intermediate Similarity	NPD1254	Approved
0.7943	Intermediate Similarity	NPD1255	Approved
0.7943	Intermediate Similarity	NPD1253	Approved
0.7911	Intermediate Similarity	NPD6203	Clinical (unspecified phase)
0.7871	Intermediate Similarity	NPD5021	Discontinued
0.7857	Intermediate Similarity	NPD5744	Clinical (unspecified phase)
0.7785	Intermediate Similarity	NPD3833	Phase 3
0.7785	Intermediate Similarity	NPD3835	Phase 3
0.777	Intermediate Similarity	NPD4547	Phase 3
0.7727	Intermediate Similarity	NPD972	Clinical (unspecified phase)
0.7671	Intermediate Similarity	NPD1592	Phase 3
0.7662	Intermediate Similarity	NPD1403	Approved
0.7662	Intermediate Similarity	NPD1404	Approved
0.7658	Intermediate Similarity	NPD3610	Approved
0.7658	Intermediate Similarity	NPD3609	Approved
0.7643	Intermediate Similarity	NPD2641	Approved
0.7643	Intermediate Similarity	NPD5069	Clinical (unspecified phase)
0.7643	Intermediate Similarity	NPD2640	Approved
0.761	Intermediate Similarity	NPD4112	Clinical (unspecified phase)
0.7595	Intermediate Similarity	NPD1325	Approved
0.7595	Intermediate Similarity	NPD1326	Approved
0.7593	Intermediate Similarity	NPD8464	Clinical (unspecified phase)
0.7593	Intermediate Similarity	NPD5473	Discontinued
0.758	Intermediate Similarity	NPD2642	Approved
0.758	Intermediate Similarity	NPD2639	Approved
0.7562	Intermediate Similarity	NPD4128	Approved
0.7562	Intermediate Similarity	NPD5065	Approved
0.7534	Intermediate Similarity	NPD680	Discontinued
0.7532	Intermediate Similarity	NPD2185	Clinical (unspecified phase)
0.753	Intermediate Similarity	NPD8431	Approved
0.7516	Intermediate Similarity	NPD4075	Phase 2
0.7515	Intermediate Similarity	NPD6610	Clinical (unspecified phase)
0.7469	Intermediate Similarity	NPD3505	Approved
0.7469	Intermediate Similarity	NPD4181	Approved
0.7469	Intermediate Similarity	NPD3506	Approved
0.745	Intermediate Similarity	NPD3401	Clinical (unspecified phase)
0.745	Intermediate Similarity	NPD4509	Discontinued
0.7423	Intermediate Similarity	NPD4076	Approved
0.7423	Intermediate Similarity	NPD4079	Approved
0.7419	Intermediate Similarity	NPD4326	Phase 2
0.7394	Intermediate Similarity	NPD5106	Approved
0.7394	Intermediate Similarity	NPD5105	Approved
0.7386	Intermediate Similarity	NPD6158	Phase 2
0.7386	Intermediate Similarity	NPD6476	Clinical (unspecified phase)
0.7383	Intermediate Similarity	NPD2006	Phase 2
0.7383	Intermediate Similarity	NPD4047	Discontinued
0.7378	Intermediate Similarity	NPD6277	Clinical (unspecified phase)
0.7378	Intermediate Similarity	NPD6595	Phase 3
0.7376	Intermediate Similarity	NPD991	Phase 2
0.7376	Intermediate Similarity	NPD992	Clinical (unspecified phase)
0.7375	Intermediate Similarity	NPD5436	Phase 1
0.7368	Intermediate Similarity	NPD2430	Phase 2
0.7355	Intermediate Similarity	NPD2150	Discontinued
0.7343	Intermediate Similarity	NPD3476	Approved
0.7343	Intermediate Similarity	NPD3475	Approved
0.7333	Intermediate Similarity	NPD1895	Discontinued
0.7329	Intermediate Similarity	NPD6827	Clinical (unspecified phase)
0.7329	Intermediate Similarity	NPD6828	Phase 2
0.7317	Intermediate Similarity	NPD6448	Phase 1
0.7317	Intermediate Similarity	NPD8386	Phase 2
0.7315	Intermediate Similarity	NPD3834	Clinical (unspecified phase)
0.7312	Intermediate Similarity	NPD4779	Clinical (unspecified phase)
0.7287	Intermediate Similarity	NPD993	Approved
0.7287	Intermediate Similarity	NPD990	Approved
0.7273	Intermediate Similarity	NPD2882	Phase 1
0.7267	Intermediate Similarity	NPD4184	Clinical (unspecified phase)
0.7266	Intermediate Similarity	NPD1561	Phase 2
0.7256	Intermediate Similarity	NPD2144	Approved
0.7255	Intermediate Similarity	NPD5538	Clinical (unspecified phase)
0.7254	Intermediate Similarity	NPD2119	Approved
0.7254	Intermediate Similarity	NPD2118	Approved
0.7246	Intermediate Similarity	NPD3607	Clinical (unspecified phase)
0.7244	Intermediate Similarity	NPD2580	Discontinued
0.7239	Intermediate Similarity	NPD3799	Suspended
0.7219	Intermediate Similarity	NPD6141	Clinical (unspecified phase)
0.7197	Intermediate Similarity	NPD1192	Clinical (unspecified phase)
0.7193	Intermediate Similarity	NPD6630	Clinical (unspecified phase)
0.7186	Intermediate Similarity	NPD3319	Phase 1
0.7186	Intermediate Similarity	NPD3318	Approved
0.7186	Intermediate Similarity	NPD3320	Approved
0.717	Intermediate Similarity	NPD5315	Discontinued
0.7169	Intermediate Similarity	NPD702	Clinical (unspecified phase)
0.716	Intermediate Similarity	NPD4426	Clinical (unspecified phase)
0.716	Intermediate Similarity	NPD6217	Discontinued
0.7152	Intermediate Similarity	NPD2007	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD4398	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD5787	Discontinued
0.7135	Intermediate Similarity	NPD5145	Clinical (unspecified phase)
0.7126	Intermediate Similarity	NPD1707	Approved
0.7126	Intermediate Similarity	NPD1708	Approved
0.7126	Intermediate Similarity	NPD6449	Clinical (unspecified phase)
0.7126	Intermediate Similarity	NPD3038	Discontinued
0.7122	Intermediate Similarity	NPD4811	Discontinued
0.7118	Intermediate Similarity	NPD5590	Clinical (unspecified phase)
0.7118	Intermediate Similarity	NPD3961	Discontinued
0.7118	Intermediate Similarity	NPD3486	Clinical (unspecified phase)
0.7105	Intermediate Similarity	NPD1918	Clinical (unspecified phase)
0.7093	Intermediate Similarity	NPD5913	Phase 3
0.7093	Intermediate Similarity	NPD5912	Clinical (unspecified phase)
0.7081	Intermediate Similarity	NPD4550	Clinical (unspecified phase)
0.7075	Intermediate Similarity	NPD4030	Approved
0.7075	Intermediate Similarity	NPD4029	Approved
0.7075	Intermediate Similarity	NPD3944	Approved
0.7075	Intermediate Similarity	NPD4028	Approved
0.7075	Intermediate Similarity	NPD3942	Approved
0.707	Intermediate Similarity	NPD1597	Phase 1
0.7044	Intermediate Similarity	NPD1554	Clinical (unspecified phase)
0.7041	Intermediate Similarity	NPD7564	Discontinued
0.7037	Intermediate Similarity	NPD2392	Clinical (unspecified phase)
0.703	Intermediate Similarity	NPD482	Approved
0.7025	Intermediate Similarity	NPD2748	Clinical (unspecified phase)
0.7025	Intermediate Similarity	NPD2927	Phase 3
0.7024	Intermediate Similarity	NPD4399	Phase 2
0.7019	Intermediate Similarity	NPD5140	Approved
0.7019	Intermediate Similarity	NPD5138	Approved
0.6994	Remote Similarity	NPD4638	Approved
0.6994	Remote Similarity	NPD4639	Approved
0.6994	Remote Similarity	NPD6180	Clinical (unspecified phase)
0.6994	Remote Similarity	NPD4640	Approved
0.6989	Remote Similarity	NPD7948	Phase 1
0.6988	Remote Similarity	NPD749	Clinical (unspecified phase)
0.6982	Remote Similarity	NPD5728	Clinical (unspecified phase)
0.6981	Remote Similarity	NPD2330	Approved
0.6981	Remote Similarity	NPD2865	Clinical (unspecified phase)
0.6977	Remote Similarity	NPD8110	Clinical (unspecified phase)
0.6975	Remote Similarity	NPD2720	Phase 1
0.6975	Remote Similarity	NPD2719	Clinical (unspecified phase)
0.6962	Remote Similarity	NPD975	Approved
0.6962	Remote Similarity	NPD6285	Phase 2
0.6962	Remote Similarity	NPD2165	Phase 1
0.6962	Remote Similarity	NPD976	Approved
0.6962	Remote Similarity	NPD977	Approved
0.6957	Remote Similarity	NPD2385	Clinical (unspecified phase)
0.6944	Remote Similarity	NPD9583	Approved
0.6936	Remote Similarity	NPD4499	Approved
0.6933	Remote Similarity	NPD1248	Discontinued
0.6932	Remote Similarity	NPD6278	Clinical (unspecified phase)
0.6932	Remote Similarity	NPD2960	Clinical (unspecified phase)
0.6928	Remote Similarity	NPD6492	Phase 2
0.6923	Remote Similarity	NPD4649	Clinical (unspecified phase)
0.6919	Remote Similarity	NPD2310	Clinical (unspecified phase)
0.6918	Remote Similarity	NPD3114	Approved
0.6918	Remote Similarity	NPD3112	Approved
0.6918	Remote Similarity	NPD473	Clinical (unspecified phase)
0.6918	Remote Similarity	NPD3113	Approved
0.6918	Remote Similarity	NPD3115	Approved
0.6914	Remote Similarity	NPD5575	Clinical (unspecified phase)
0.6899	Remote Similarity	NPD4297	Phase 1
0.6894	Remote Similarity	NPD6454	Clinical (unspecified phase)
0.689	Remote Similarity	NPD2844	Phase 3
0.6886	Remote Similarity	NPD2382	Approved
0.6886	Remote Similarity	NPD2381	Approved
0.6886	Remote Similarity	NPD6375	Clinical (unspecified phase)
0.6886	Remote Similarity	NPD2380	Approved
0.6886	Remote Similarity	NPD4332	Phase 3
0.6882	Remote Similarity	NPD1332	Clinical (unspecified phase)
0.6882	Remote Similarity	NPD2095	Phase 2
0.6882	Remote Similarity	NPD2092	Phase 2
0.6882	Remote Similarity	NPD2094	Phase 2
0.6879	Remote Similarity	NPD1534	Approved
0.6875	Remote Similarity	NPD3791	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD7618	Phase 3
0.6875	Remote Similarity	NPD7619	Phase 3
0.6871	Remote Similarity	NPD2915	Discontinued
0.6871	Remote Similarity	NPD715	Phase 3
0.6864	Remote Similarity	NPD5962	Phase 2
0.6863	Remote Similarity	NPD5020	Approved
0.686	Remote Similarity	NPD5809	Phase 3
0.6857	Remote Similarity	NPD3404	Approved
0.6848	Remote Similarity	NPD5412	Discontinued
0.6845	Remote Similarity	NPD7111	Discontinued
0.6842	Remote Similarity	NPD2096	Phase 2
0.6842	Remote Similarity	NPD2091	Phase 2
0.6842	Remote Similarity	NPD768	Clinical (unspecified phase)
0.6839	Remote Similarity	NPD6133	Discontinued

Bioactivity similarity: Similar Natural Products in NPASS

Bioactivity similarity was calculated based on bioactivity descriptors of compounds. The bioactivity descriptors were calculated by a recently developed AI algorithm Chemical Checker (CC) [Nature Biotechnology, 38:1087–1096, 2020; Nature Communications, 12:3932, 2021], which evaluated bioactivity similarities at five levels:
☉ A: chemistry similarity;
☉ B: biological targets similarity;
☉ C: networks similarity;
☉ D: cell-based bioactivity similarity;
☉ E: similarity based on clinical data.

Those 5 categories of CC bioactivity descriptors were calculated and then subjected to manifold projection using UMAP algorithm, to project all NPs on a 2-Dimensional space. The current NP was highlighted with a small circle in the 2-D map. Below figures: left-to-right, A-to-E.

A: chemistry similarity

B: biological targets similarity

C: networks similarity

D: cell-based bioactivity similarity

E: similarity based on clinical data