NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	251.17
Volume:	289.393
LogP:	6.226
LogD:	4.81
LogS:	-6.742
# Rotatable Bonds:	5
TPSA:	15.79
# H-Bond Aceptor:	1
# H-Bond Donor:	1
# Rings:	3
# Heavy Atoms:	1

MedChem Properties

QED Drug-Likeness Score:	0.581
Synthetic Accessibility Score:	1.881
Fsp3:	0.333
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:	-4.845
MDCK Permeability:	1.146658087236574e-05
Pgp-inhibitor:	0.985
Pgp-substrate:	0.015
Human Intestinal Absorption (HIA):	0.002
20% Bioavailability (F20%):	0.947
30% Bioavailability (F30%):	0.979

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.606
Plasma Protein Binding (PPB):	98.21134948730469%
Volume Distribution (VD):	3.503
Pgp-substrate:	0.8072892427444458%

ADMET: Metabolism

CYP1A2-inhibitor:	0.985
CYP1A2-substrate:	0.343
CYP2C19-inhibitor:	0.778
CYP2C19-substrate:	0.07
CYP2C9-inhibitor:	0.509
CYP2C9-substrate:	0.904
CYP2D6-inhibitor:	0.805
CYP2D6-substrate:	0.723
CYP3A4-inhibitor:	0.566
CYP3A4-substrate:	0.174

ADMET: Excretion

Clearance (CL):	4.636
Half-life (T1/2):	0.109

ADMET: Toxicity

hERG Blockers:	0.076
Human Hepatotoxicity (H-HT):	0.121
Drug-inuced Liver Injury (DILI):	0.706
AMES Toxicity:	0.208
Rat Oral Acute Toxicity:	0.064
Maximum Recommended Daily Dose:	0.806
Skin Sensitization:	0.929
Carcinogencity:	0.554
Eye Corrosion:	0.204
Eye Irritation:	0.992
Respiratory Toxicity:	0.945

Download Data

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

Natural Product: NPC475450

Natural Product ID:	NPC475450
*Common Name:**	1-Hexyl-9H-Carbazole
IUPAC Name:	1-hexyl-9H-carbazole
Synonyms:
Standard InCHIKey:	ICZIGRGFOIYYPA-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C18H21N/c1-2-3-4-5-9-14-10-8-12-16-15-11-6-7-13-17(15)19-18(14)16/h6-8,10-13,19H,2-5,9H2,1H3
SMILES:	CCCCCCc1cccc2c1[nH]c1c2cccc1
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL505913
PubChem CID:	44576082
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	3

Activity Type	# Activity
Cell Line	1
Organism	7
Others	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT168	Cell Line	P388	Mus musculus	IC50	=	9.0	ug.mL-1	PMID[522917]
NPT19	Organism	Escherichia coli	Escherichia coli	MIC	>	60.0	ug	PMID[522917]
NPT79	Organism	Bacillus subtilis	Bacillus subtilis	MIC	>	60.0	ug	PMID[522917]
NPT18	Organism	Pseudomonas aeruginosa	Pseudomonas aeruginosa	MIC	>	60.0	ug	PMID[522917]
NPT20	Organism	Candida albicans	Candida albicans	MIC	>	60.0	ug	PMID[522917]
NPT330	Organism	Trichophyton mentagrophytes	Trichophyton mentagrophytes	MIC	=	1.9	ug	PMID[522917]
NPT1223	Organism	Amorphotheca resinae	Amorphotheca resinae	MIC	=	7.5	ug	PMID[522917]
NPT3574	Organism	Herpes simplex virus (type 1 / strain F)	Herpes simplex virus (type 1 / strain F)	IZ	=	1.0	mm	PMID[522917]
NPT27	Others	Unspecified		IZ	=	1.0	mm	PMID[522917]

☑ 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 NPC475450 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	1072
0.1-0.2	11083
0.2-0.3	17095
0.3-0.4	7973
0.4-0.5	2427
0.5-0.6	1573
0.6-0.7	993
0.7-0.8	379
0.8-0.85	59
0.85-0.9	33
0.9-0.95	3
0.95-1	7

Similarity Score	Similarity Level	Natural Product ID
0.9839	High Similarity	NPC473587
0.976	High Similarity	NPC475428
0.9758	High Similarity	NPC473762
0.9683	High Similarity	NPC179365
0.9606	High Similarity	NPC473930
0.9597	High Similarity	NPC250361
0.9274	High Similarity	NPC41174
0.9173	High Similarity	NPC312092
0.9147	High Similarity	NPC22079
0.8872	High Similarity	NPC198988
0.8824	High Similarity	NPC59084
0.8824	High Similarity	NPC2949
0.8806	High Similarity	NPC325252
0.8759	High Similarity	NPC63157
0.8759	High Similarity	NPC473868
0.8714	High Similarity	NPC477134
0.8686	High Similarity	NPC469784
0.8686	High Similarity	NPC115611
0.8686	High Similarity	NPC469783
0.8686	High Similarity	NPC469768
0.8686	High Similarity	NPC469761
0.8686	High Similarity	NPC469767
0.8686	High Similarity	NPC469779
0.8686	High Similarity	NPC469780
0.8682	High Similarity	NPC122718
0.8667	High Similarity	NPC29886
0.8667	High Similarity	NPC218268
0.8667	High Similarity	NPC261195
0.8652	High Similarity	NPC124005
0.8633	High Similarity	NPC242556
0.8623	High Similarity	NPC469766
0.8613	High Similarity	NPC88097
0.8613	High Similarity	NPC73767
0.8603	High Similarity	NPC84911
0.8592	High Similarity	NPC53947
0.8592	High Similarity	NPC33421
0.8582	High Similarity	NPC21605
0.8571	High Similarity	NPC81561
0.8551	High Similarity	NPC284635
0.8529	High Similarity	NPC96102
0.8516	High Similarity	NPC215519
0.8511	High Similarity	NPC288838
0.8504	High Similarity	NPC54102
0.8504	High Similarity	NPC162689
0.8492	Intermediate Similarity	NPC148140
0.8478	Intermediate Similarity	NPC110126
0.8467	Intermediate Similarity	NPC105127
0.8414	Intermediate Similarity	NPC38736
0.8392	Intermediate Similarity	NPC187951
0.8392	Intermediate Similarity	NPC37548
0.838	Intermediate Similarity	NPC129042
0.837	Intermediate Similarity	NPC82295
0.8356	Intermediate Similarity	NPC184476
0.8333	Intermediate Similarity	NPC125746
0.8322	Intermediate Similarity	NPC201380
0.8322	Intermediate Similarity	NPC179787
0.8311	Intermediate Similarity	NPC44773
0.8311	Intermediate Similarity	NPC215584
0.831	Intermediate Similarity	NPC314372
0.831	Intermediate Similarity	NPC204141
0.831	Intermediate Similarity	NPC470440
0.8299	Intermediate Similarity	NPC286427
0.8298	Intermediate Similarity	NPC190296
0.8286	Intermediate Similarity	NPC279081
0.8264	Intermediate Similarity	NPC2272
0.8264	Intermediate Similarity	NPC321911
0.8252	Intermediate Similarity	NPC63545
0.8243	Intermediate Similarity	NPC206819
0.8243	Intermediate Similarity	NPC474880
0.8243	Intermediate Similarity	NPC318065
0.8243	Intermediate Similarity	NPC56765
0.8243	Intermediate Similarity	NPC41257
0.8243	Intermediate Similarity	NPC475990
0.8243	Intermediate Similarity	NPC221786
0.8243	Intermediate Similarity	NPC474791
0.8219	Intermediate Similarity	NPC325903
0.8207	Intermediate Similarity	NPC105818
0.8207	Intermediate Similarity	NPC24678
0.8194	Intermediate Similarity	NPC469811
0.8188	Intermediate Similarity	NPC229173
0.8188	Intermediate Similarity	NPC473320
0.8176	Intermediate Similarity	NPC76982
0.8176	Intermediate Similarity	NPC216643
0.8163	Intermediate Similarity	NPC471458
0.8163	Intermediate Similarity	NPC470507
0.8156	Intermediate Similarity	NPC230002
0.8151	Intermediate Similarity	NPC470233
0.8133	Intermediate Similarity	NPC16667
0.8125	Intermediate Similarity	NPC143872
0.8121	Intermediate Similarity	NPC92796
0.8121	Intermediate Similarity	NPC135141
0.8108	Intermediate Similarity	NPC285469
0.8095	Intermediate Similarity	NPC259644
0.8095	Intermediate Similarity	NPC469786
0.8095	Intermediate Similarity	NPC73952
0.8095	Intermediate Similarity	NPC469760
0.8095	Intermediate Similarity	NPC469765
0.8095	Intermediate Similarity	NPC25008
0.8095	Intermediate Similarity	NPC469763
0.8082	Intermediate Similarity	NPC148592
0.8079	Intermediate Similarity	NPC162799
0.8079	Intermediate Similarity	NPC271734
0.8079	Intermediate Similarity	NPC90723
0.8069	Intermediate Similarity	NPC471957
0.8056	Intermediate Similarity	NPC159856
0.8054	Intermediate Similarity	NPC299594
0.8041	Intermediate Similarity	NPC212376
0.8041	Intermediate Similarity	NPC75540
0.8041	Intermediate Similarity	NPC207726
0.8041	Intermediate Similarity	NPC80597
0.8041	Intermediate Similarity	NPC211572
0.8041	Intermediate Similarity	NPC70922
0.7973	Intermediate Similarity	NPC200214
0.7958	Intermediate Similarity	NPC104483
0.7943	Intermediate Similarity	NPC150259
0.7943	Intermediate Similarity	NPC314102
0.7943	Intermediate Similarity	NPC251722
0.7933	Intermediate Similarity	NPC236711
0.7922	Intermediate Similarity	NPC154293
0.7922	Intermediate Similarity	NPC201700
0.7919	Intermediate Similarity	NPC476219
0.7919	Intermediate Similarity	NPC476297
0.7905	Intermediate Similarity	NPC470823
0.7895	Intermediate Similarity	NPC470203
0.7881	Intermediate Similarity	NPC67056
0.7871	Intermediate Similarity	NPC280548
0.7871	Intermediate Similarity	NPC474897
0.7871	Intermediate Similarity	NPC194411
0.7867	Intermediate Similarity	NPC469785
0.7852	Intermediate Similarity	NPC141926
0.7843	Intermediate Similarity	NPC21174
0.7843	Intermediate Similarity	NPC271797
0.7843	Intermediate Similarity	NPC472587
0.7843	Intermediate Similarity	NPC317105
0.7843	Intermediate Similarity	NPC8104
0.7829	Intermediate Similarity	NPC470204
0.7821	Intermediate Similarity	NPC6982
0.7815	Intermediate Similarity	NPC469762
0.7806	Intermediate Similarity	NPC63751
0.78	Intermediate Similarity	NPC34844
0.7793	Intermediate Similarity	NPC20144
0.7785	Intermediate Similarity	NPC216713
0.7771	Intermediate Similarity	NPC97525
0.7771	Intermediate Similarity	NPC34508
0.7762	Intermediate Similarity	NPC169433
0.7748	Intermediate Similarity	NPC141353
0.7742	Intermediate Similarity	NPC474561
0.7742	Intermediate Similarity	NPC49954
0.7737	Intermediate Similarity	NPC476140
0.7733	Intermediate Similarity	NPC161108
0.7727	Intermediate Similarity	NPC194640
0.7727	Intermediate Similarity	NPC40779
0.7727	Intermediate Similarity	NPC311276
0.7722	Intermediate Similarity	NPC275305
0.7722	Intermediate Similarity	NPC329688
0.7722	Intermediate Similarity	NPC189812
0.7722	Intermediate Similarity	NPC37423
0.7712	Intermediate Similarity	NPC122141
0.7677	Intermediate Similarity	NPC115232
0.7677	Intermediate Similarity	NPC470508
0.7673	Intermediate Similarity	NPC288785
0.7673	Intermediate Similarity	NPC280852
0.7662	Intermediate Similarity	NPC282231
0.7658	Intermediate Similarity	NPC477611
0.7647	Intermediate Similarity	NPC46358
0.7635	Intermediate Similarity	NPC316069
0.7628	Intermediate Similarity	NPC470509
0.7628	Intermediate Similarity	NPC160105
0.7628	Intermediate Similarity	NPC109447
0.7625	Intermediate Similarity	NPC151939
0.7625	Intermediate Similarity	NPC68354
0.7616	Intermediate Similarity	NPC232798
0.7616	Intermediate Similarity	NPC200743
0.7613	Intermediate Similarity	NPC247987
0.7607	Intermediate Similarity	NPC190007
0.76	Intermediate Similarity	NPC40070
0.7597	Intermediate Similarity	NPC279918
0.7595	Intermediate Similarity	NPC82331
0.7584	Intermediate Similarity	NPC470111
0.7584	Intermediate Similarity	NPC114209
0.758	Intermediate Similarity	NPC317430
0.7578	Intermediate Similarity	NPC176199
0.7578	Intermediate Similarity	NPC6093
0.7578	Intermediate Similarity	NPC88363
0.7578	Intermediate Similarity	NPC270009
0.7578	Intermediate Similarity	NPC215795
0.7578	Intermediate Similarity	NPC213468
0.7564	Intermediate Similarity	NPC274229
0.7562	Intermediate Similarity	NPC474958
0.7561	Intermediate Similarity	NPC473189
0.7561	Intermediate Similarity	NPC94943
0.7548	Intermediate Similarity	NPC214106
0.7547	Intermediate Similarity	NPC161861
0.7547	Intermediate Similarity	NPC472123
0.7532	Intermediate Similarity	NPC230869
0.7531	Intermediate Similarity	NPC198339
0.7531	Intermediate Similarity	NPC300688
0.7531	Intermediate Similarity	NPC314919
0.7519	Intermediate Similarity	NPC476566
0.7517	Intermediate Similarity	NPC478186

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 NPC475450 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	489
0.1-0.2	785
0.2-0.3	1041
0.3-0.4	2082
0.4-0.5	2430
0.5-0.6	1621
0.6-0.7	573
0.7-0.8	107
0.8-0.85	14
0.85-0.9	6
0.9-0.95	2
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9185	High Similarity	NPD5254	Discontinued
0.9104	High Similarity	NPD3943	Clinical (unspecified phase)
0.8881	High Similarity	NPD1262	Discovery
0.8652	High Similarity	NPD3100	Discontinued
0.8613	High Similarity	NPD786	Approved
0.8593	High Similarity	NPD4880	Discontinued
0.8592	High Similarity	NPD4463	Approved
0.8592	High Similarity	NPD4462	Approved
0.8561	High Similarity	NPD4637	Clinical (unspecified phase)
0.8529	High Similarity	NPD198	Clinical (unspecified phase)
0.8521	High Similarity	NPD4374	Clinical (unspecified phase)
0.8519	High Similarity	NPD3385	Approved
0.8489	Intermediate Similarity	NPD1722	Approved
0.8462	Intermediate Similarity	NPD2172	Phase 1
0.838	Intermediate Similarity	NPD1683	Approved
0.838	Intermediate Similarity	NPD1528	Clinical (unspecified phase)
0.8358	Intermediate Similarity	NPD3654	Approved
0.8222	Intermediate Similarity	NPD947	Approved
0.8219	Intermediate Similarity	NPD2837	Discontinued
0.82	Intermediate Similarity	NPD3323	Discontinued
0.8082	Intermediate Similarity	NPD3835	Phase 3
0.8082	Intermediate Similarity	NPD3833	Phase 3
0.8071	Intermediate Similarity	NPD6554	Approved
0.8071	Intermediate Similarity	NPD45	Approved
0.8026	Intermediate Similarity	NPD5744	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD1253	Approved
0.8	Intermediate Similarity	NPD1254	Approved
0.8	Intermediate Similarity	NPD1256	Approved
0.8	Intermediate Similarity	NPD1255	Approved
0.7971	Intermediate Similarity	NPD1251	Discontinued
0.7947	Intermediate Similarity	NPD1404	Approved
0.7947	Intermediate Similarity	NPD1403	Approved
0.7945	Intermediate Similarity	NPD4547	Phase 3
0.7922	Intermediate Similarity	NPD2641	Approved
0.7922	Intermediate Similarity	NPD2640	Approved
0.7871	Intermediate Similarity	NPD1325	Approved
0.7871	Intermediate Similarity	NPD1326	Approved
0.7857	Intermediate Similarity	NPD2642	Approved
0.7857	Intermediate Similarity	NPD2639	Approved
0.7847	Intermediate Similarity	NPD1592	Phase 3
0.7821	Intermediate Similarity	NPD3609	Approved
0.7821	Intermediate Similarity	NPD3610	Approved
0.7806	Intermediate Similarity	NPD5069	Clinical (unspecified phase)
0.7806	Intermediate Similarity	NPD2185	Clinical (unspecified phase)
0.7806	Intermediate Similarity	NPD5021	Discontinued
0.7778	Intermediate Similarity	NPD972	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD1853	Clinical (unspecified phase)
0.7771	Intermediate Similarity	NPD4112	Clinical (unspecified phase)
0.7736	Intermediate Similarity	NPD6203	Clinical (unspecified phase)
0.7722	Intermediate Similarity	NPD4128	Approved
0.7708	Intermediate Similarity	NPD680	Discontinued
0.7673	Intermediate Similarity	NPD4075	Phase 2
0.7671	Intermediate Similarity	NPD2006	Phase 2
0.7654	Intermediate Similarity	NPD5105	Approved
0.7654	Intermediate Similarity	NPD5106	Approved
0.7651	Intermediate Similarity	NPD2430	Phase 2
0.7643	Intermediate Similarity	NPD3475	Approved
0.7643	Intermediate Similarity	NPD3476	Approved
0.7632	Intermediate Similarity	NPD2150	Discontinued
0.7625	Intermediate Similarity	NPD4181	Approved
0.7625	Intermediate Similarity	NPD3505	Approved
0.7625	Intermediate Similarity	NPD3506	Approved
0.7619	Intermediate Similarity	NPD3401	Clinical (unspecified phase)
0.7619	Intermediate Similarity	NPD4509	Discontinued
0.761	Intermediate Similarity	NPD5065	Approved
0.7603	Intermediate Similarity	NPD3834	Clinical (unspecified phase)
0.7578	Intermediate Similarity	NPD4076	Approved
0.7578	Intermediate Similarity	NPD8386	Phase 2
0.7578	Intermediate Similarity	NPD4079	Approved
0.7561	Intermediate Similarity	NPD6610	Clinical (unspecified phase)
0.7554	Intermediate Similarity	NPD2118	Approved
0.7554	Intermediate Similarity	NPD2119	Approved
0.7551	Intermediate Similarity	NPD4047	Discontinued
0.7532	Intermediate Similarity	NPD5436	Phase 1
0.7532	Intermediate Similarity	NPD4184	Clinical (unspecified phase)
0.7531	Intermediate Similarity	NPD6595	Phase 3
0.7531	Intermediate Similarity	NPD8464	Clinical (unspecified phase)
0.7531	Intermediate Similarity	NPD5473	Discontinued
0.7516	Intermediate Similarity	NPD2580	Discontinued
0.7516	Intermediate Similarity	NPD2144	Approved
0.75	Intermediate Similarity	NPD3607	Clinical (unspecified phase)
0.7484	Intermediate Similarity	NPD6828	Phase 2
0.7484	Intermediate Similarity	NPD6827	Clinical (unspecified phase)
0.747	Intermediate Similarity	NPD8431	Approved
0.7468	Intermediate Similarity	NPD4779	Clinical (unspecified phase)
0.7468	Intermediate Similarity	NPD4326	Phase 2
0.7445	Intermediate Similarity	NPD1561	Phase 2
0.7439	Intermediate Similarity	NPD3319	Phase 1
0.7439	Intermediate Similarity	NPD3320	Approved
0.7439	Intermediate Similarity	NPD3318	Approved
0.7434	Intermediate Similarity	NPD2882	Phase 1
0.7429	Intermediate Similarity	NPD991	Phase 2
0.7429	Intermediate Similarity	NPD992	Clinical (unspecified phase)
0.7423	Intermediate Similarity	NPD6277	Clinical (unspecified phase)
0.7417	Intermediate Similarity	NPD5538	Clinical (unspecified phase)
0.7378	Intermediate Similarity	NPD3038	Discontinued
0.7378	Intermediate Similarity	NPD1707	Approved
0.7378	Intermediate Similarity	NPD1708	Approved
0.7361	Intermediate Similarity	NPD4029	Approved
0.7361	Intermediate Similarity	NPD4028	Approved
0.7361	Intermediate Similarity	NPD4030	Approved
0.7325	Intermediate Similarity	NPD5315	Discontinued
0.732	Intermediate Similarity	NPD6158	Phase 2
0.732	Intermediate Similarity	NPD6476	Clinical (unspecified phase)
0.7319	Intermediate Similarity	NPD5787	Discontinued
0.7317	Intermediate Similarity	NPD702	Clinical (unspecified phase)
0.7315	Intermediate Similarity	NPD2007	Clinical (unspecified phase)
0.7305	Intermediate Similarity	NPD4426	Clinical (unspecified phase)
0.7305	Intermediate Similarity	NPD6217	Discontinued
0.7278	Intermediate Similarity	NPD5140	Approved
0.7278	Intermediate Similarity	NPD5138	Approved
0.7273	Intermediate Similarity	NPD1895	Discontinued
0.7262	Intermediate Similarity	NPD5590	Clinical (unspecified phase)
0.7262	Intermediate Similarity	NPD3486	Clinical (unspecified phase)
0.7262	Intermediate Similarity	NPD3961	Discontinued
0.7244	Intermediate Similarity	NPD2865	Clinical (unspecified phase)
0.7244	Intermediate Similarity	NPD1192	Clinical (unspecified phase)
0.7241	Intermediate Similarity	NPD3942	Approved
0.7241	Intermediate Similarity	NPD3944	Approved
0.7235	Intermediate Similarity	NPD6630	Clinical (unspecified phase)
0.7233	Intermediate Similarity	NPD4550	Clinical (unspecified phase)
0.7226	Intermediate Similarity	NPD1597	Phase 1
0.7226	Intermediate Similarity	NPD2165	Phase 1
0.7219	Intermediate Similarity	NPD8110	Clinical (unspecified phase)
0.7215	Intermediate Similarity	NPD2385	Clinical (unspecified phase)
0.7209	Intermediate Similarity	NPD993	Approved
0.7209	Intermediate Similarity	NPD990	Approved
0.7197	Intermediate Similarity	NPD1554	Clinical (unspecified phase)
0.7179	Intermediate Similarity	NPD3112	Approved
0.7179	Intermediate Similarity	NPD3114	Approved
0.7179	Intermediate Similarity	NPD3115	Approved
0.7179	Intermediate Similarity	NPD3113	Approved
0.7178	Intermediate Similarity	NPD3799	Suspended
0.7176	Intermediate Similarity	NPD5145	Clinical (unspecified phase)
0.7174	Intermediate Similarity	NPD4811	Discontinued
0.716	Intermediate Similarity	NPD6141	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD6448	Phase 1
0.7152	Intermediate Similarity	NPD1918	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD4640	Approved
0.7143	Intermediate Similarity	NPD4639	Approved
0.7143	Intermediate Similarity	NPD2844	Phase 3
0.7143	Intermediate Similarity	NPD4638	Approved
0.7135	Intermediate Similarity	NPD5913	Phase 3
0.7135	Intermediate Similarity	NPD5912	Clinical (unspecified phase)
0.7134	Intermediate Similarity	NPD2330	Approved
0.7134	Intermediate Similarity	NPD749	Clinical (unspecified phase)
0.7133	Intermediate Similarity	NPD5020	Approved
0.7126	Intermediate Similarity	NPD1332	Clinical (unspecified phase)
0.7126	Intermediate Similarity	NPD5728	Clinical (unspecified phase)
0.7115	Intermediate Similarity	NPD6285	Phase 2
0.7113	Intermediate Similarity	NPD9583	Approved
0.711	Intermediate Similarity	NPD3791	Clinical (unspecified phase)
0.7108	Intermediate Similarity	NPD5962	Phase 2
0.7091	Intermediate Similarity	NPD4398	Clinical (unspecified phase)
0.7081	Intermediate Similarity	NPD2392	Clinical (unspecified phase)
0.7081	Intermediate Similarity	NPD1248	Discontinued
0.7076	Intermediate Similarity	NPD4499	Approved
0.7073	Intermediate Similarity	NPD482	Approved
0.707	Intermediate Similarity	NPD2927	Phase 3
0.707	Intermediate Similarity	NPD473	Clinical (unspecified phase)
0.7069	Intermediate Similarity	NPD2960	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD2310	Clinical (unspecified phase)
0.7044	Intermediate Similarity	NPD6074	Clinical (unspecified phase)
0.7035	Intermediate Similarity	NPD6180	Clinical (unspecified phase)
0.7034	Intermediate Similarity	NPD715	Phase 3
0.7024	Intermediate Similarity	NPD2094	Phase 2
0.7024	Intermediate Similarity	NPD2095	Phase 2
0.7024	Intermediate Similarity	NPD2092	Phase 2
0.7019	Intermediate Similarity	NPD2915	Discontinued
0.7018	Intermediate Similarity	NPD1534	Approved
0.7011	Intermediate Similarity	NPD7619	Phase 3
0.7011	Intermediate Similarity	NPD7618	Phase 3
0.7007	Intermediate Similarity	NPD7481	Approved
0.7007	Intermediate Similarity	NPD7480	Approved
0.7	Intermediate Similarity	NPD271	Approved
0.7	Intermediate Similarity	NPD2072	Approved
0.7	Intermediate Similarity	NPD2069	Approved
0.7	Intermediate Similarity	NPD268	Approved
0.7	Intermediate Similarity	NPD270	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD2075	Approved
0.7	Intermediate Similarity	NPD2068	Approved
0.7	Intermediate Similarity	NPD2073	Approved
0.7	Intermediate Similarity	NPD2071	Approved
0.7	Intermediate Similarity	NPD2070	Approved
0.7	Intermediate Similarity	NPD2074	Approved
0.6988	Remote Similarity	NPD7111	Discontinued
0.6982	Remote Similarity	NPD2091	Phase 2
0.6982	Remote Similarity	NPD7564	Discontinued
0.6982	Remote Similarity	NPD2096	Phase 2
0.6972	Remote Similarity	NPD9357	Approved
0.6971	Remote Similarity	NPD6449	Clinical (unspecified phase)
0.6968	Remote Similarity	NPD3852	Clinical (unspecified phase)
0.6966	Remote Similarity	NPD4511	Phase 1
0.6966	Remote Similarity	NPD6451	Discontinued
0.6964	Remote Similarity	NPD4399	Phase 2
0.6964	Remote Similarity	NPD4649	Clinical (unspecified phase)
0.6962	Remote Similarity	NPD2748	Clinical (unspecified phase)
0.6954	Remote Similarity	NPD5575	Clinical (unspecified phase)
0.6951	Remote Similarity	NPD5934	Clinical (unspecified phase)
0.6946	Remote Similarity	NPD40	Phase 2

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