NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	193.09
Volume:	217.572
LogP:	4.244
LogD:	3.825
LogS:	-5.515
# 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:	0.602
Synthetic Accessibility Score:	2.133
Fsp3:	0.0
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.862
MDCK Permeability:	1.2648592019104399e-05
Pgp-inhibitor:	0.064
Pgp-substrate:	0.004
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.951
30% Bioavailability (F30%):	0.467

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.77
Plasma Protein Binding (PPB):	95.49395751953125%
Volume Distribution (VD):	0.851
Pgp-substrate:	1.7000319957733154%

ADMET: Metabolism

CYP1A2-inhibitor:	0.993
CYP1A2-substrate:	0.76
CYP2C19-inhibitor:	0.716
CYP2C19-substrate:	0.382
CYP2C9-inhibitor:	0.632
CYP2C9-substrate:	0.916
CYP2D6-inhibitor:	0.843
CYP2D6-substrate:	0.91
CYP3A4-inhibitor:	0.512
CYP3A4-substrate:	0.273

ADMET: Excretion

Clearance (CL):	5.034
Half-life (T1/2):	0.225

ADMET: Toxicity

hERG Blockers:	0.012
Human Hepatotoxicity (H-HT):	0.315
Drug-inuced Liver Injury (DILI):	0.862
AMES Toxicity:	0.753
Rat Oral Acute Toxicity:	0.115
Maximum Recommended Daily Dose:	0.729
Skin Sensitization:	0.932
Carcinogencity:	0.832
Eye Corrosion:	0.527
Eye Irritation:	0.994
Respiratory Toxicity:	0.975

Download Data

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

Natural Product: NPC473762

Natural Product ID:	NPC473762
*Common Name:**	Pavettine
IUPAC Name:	1-ethenyl-9H-carbazole
Synonyms:	Pavettine
Standard InCHIKey:	APQXWKHOGQFGTB-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C14H11N/c1-2-10-6-5-8-12-11-7-3-4-9-13(11)15-14(10)12/h2-9,15H,1H2
SMILES:	C=Cc1cccc2c1[nH]c1c2cccc1
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL451160
PubChem CID:	15114296
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	8
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT168	Cell Line	P388	Mus musculus	IC50	=	0.1	ug.mL-1	PMID[551627]
NPT19	Organism	Escherichia coli	Escherichia coli	MIC	=	30.0	ug	PMID[551627]
NPT79	Organism	Bacillus subtilis	Bacillus subtilis	MIC	=	1.9	ug	PMID[551627]
NPT18	Organism	Pseudomonas aeruginosa	Pseudomonas aeruginosa	MIC	>	60.0	ug	PMID[551627]
NPT20	Organism	Candida albicans	Candida albicans	MIC	=	1.9	ug	PMID[551627]
NPT330	Organism	Trichophyton mentagrophytes	Trichophyton mentagrophytes	MIC	=	0.1	ug	PMID[551627]
NPT1223	Organism	Amorphotheca resinae	Amorphotheca resinae	MIC	=	0.9	ug	PMID[551627]
NPT3574	Organism	Herpes simplex virus (type 1 / strain F)	Herpes simplex virus (type 1 / strain F)	IZ	=	1.0	mm	PMID[551627]
NPT1106	Organism	Human poliovirus 1	Human poliovirus 1	IZ	=	1.0	mm	PMID[551627]
NPT27	Others	Unspecified		IZ	=	2.0	mm	PMID[551627]

☑ 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 NPC473762 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	1224
0.1-0.2	13160
0.2-0.3	16621
0.3-0.4	6501
0.4-0.5	2274
0.5-0.6	1531
0.6-0.7	954
0.7-0.8	342
0.8-0.85	53
0.85-0.9	26
0.9-0.95	4
0.95-1	7

Similarity Score	Similarity Level	Natural Product ID
0.9918	High Similarity	NPC473587
0.9837	High Similarity	NPC475428
0.9835	High Similarity	NPC250361
0.9758	High Similarity	NPC179365
0.9758	High Similarity	NPC475450
0.968	High Similarity	NPC473930
0.9344	High Similarity	NPC41174
0.9237	High Similarity	NPC312092
0.9213	High Similarity	NPC22079
0.8931	High Similarity	NPC198988
0.8864	High Similarity	NPC325252
0.8741	High Similarity	NPC284635
0.8741	High Similarity	NPC115611
0.8722	High Similarity	NPC29886
0.8722	High Similarity	NPC96102
0.8722	High Similarity	NPC218268
0.8722	High Similarity	NPC261195
0.871	High Similarity	NPC54102
0.871	High Similarity	NPC162689
0.8667	High Similarity	NPC88097
0.8657	High Similarity	NPC84911
0.8657	High Similarity	NPC105127
0.8603	High Similarity	NPC59084
0.8603	High Similarity	NPC2949
0.8594	High Similarity	NPC122718
0.8571	High Similarity	NPC215519
0.8561	High Similarity	NPC82295
0.8561	High Similarity	NPC288838
0.8548	High Similarity	NPC148140
0.854	High Similarity	NPC473868
0.854	High Similarity	NPC63157
0.8529	High Similarity	NPC110126
0.8529	High Similarity	NPC73767
0.8519	High Similarity	NPC125746
0.85	High Similarity	NPC477134
0.848	Intermediate Similarity	NPC81561
0.8467	Intermediate Similarity	NPC469784
0.8467	Intermediate Similarity	NPC279081
0.8467	Intermediate Similarity	NPC469779
0.8467	Intermediate Similarity	NPC469767
0.8467	Intermediate Similarity	NPC469768
0.8467	Intermediate Similarity	NPC469783
0.8467	Intermediate Similarity	NPC469780
0.8467	Intermediate Similarity	NPC469761
0.844	Intermediate Similarity	NPC124005
0.8429	Intermediate Similarity	NPC63545
0.8417	Intermediate Similarity	NPC242556
0.8406	Intermediate Similarity	NPC469766
0.838	Intermediate Similarity	NPC53947
0.838	Intermediate Similarity	NPC33421
0.8369	Intermediate Similarity	NPC469811
0.8369	Intermediate Similarity	NPC21605
0.8369	Intermediate Similarity	NPC201380
0.8369	Intermediate Similarity	NPC179787
0.8357	Intermediate Similarity	NPC470440
0.8357	Intermediate Similarity	NPC204141
0.8345	Intermediate Similarity	NPC190296
0.8345	Intermediate Similarity	NPC76982
0.8333	Intermediate Similarity	NPC230002
0.831	Intermediate Similarity	NPC321911
0.8298	Intermediate Similarity	NPC143872
0.8288	Intermediate Similarity	NPC474791
0.8264	Intermediate Similarity	NPC325903
0.8231	Intermediate Similarity	NPC215584
0.8231	Intermediate Similarity	NPC44773
0.8227	Intermediate Similarity	NPC159856
0.8227	Intermediate Similarity	NPC314372
0.8207	Intermediate Similarity	NPC38736
0.8182	Intermediate Similarity	NPC187951
0.8182	Intermediate Similarity	NPC37548
0.8169	Intermediate Similarity	NPC129042
0.8151	Intermediate Similarity	NPC184476
0.8125	Intermediate Similarity	NPC148592
0.8112	Intermediate Similarity	NPC471957
0.8095	Intermediate Similarity	NPC216643
0.8095	Intermediate Similarity	NPC286427
0.8056	Intermediate Similarity	NPC2272
0.8041	Intermediate Similarity	NPC206819
0.8041	Intermediate Similarity	NPC92796
0.8041	Intermediate Similarity	NPC135141
0.8041	Intermediate Similarity	NPC474880
0.8041	Intermediate Similarity	NPC318065
0.8041	Intermediate Similarity	NPC56765
0.8041	Intermediate Similarity	NPC475990
0.8041	Intermediate Similarity	NPC221786
0.8041	Intermediate Similarity	NPC41257
0.8	Intermediate Similarity	NPC24678
0.8	Intermediate Similarity	NPC105818
0.7987	Intermediate Similarity	NPC229173
0.7987	Intermediate Similarity	NPC473320
0.7973	Intermediate Similarity	NPC236711
0.7959	Intermediate Similarity	NPC471458
0.7959	Intermediate Similarity	NPC470507
0.7945	Intermediate Similarity	NPC470823
0.7945	Intermediate Similarity	NPC470233
0.7945	Intermediate Similarity	NPC216713
0.7933	Intermediate Similarity	NPC16667
0.7929	Intermediate Similarity	NPC169433
0.7905	Intermediate Similarity	NPC285469
0.7905	Intermediate Similarity	NPC141353
0.7891	Intermediate Similarity	NPC73952
0.7891	Intermediate Similarity	NPC469765
0.7891	Intermediate Similarity	NPC25008
0.7891	Intermediate Similarity	NPC469786
0.7891	Intermediate Similarity	NPC141926
0.7891	Intermediate Similarity	NPC259644
0.7891	Intermediate Similarity	NPC200214
0.7891	Intermediate Similarity	NPC469763
0.7891	Intermediate Similarity	NPC469760
0.7881	Intermediate Similarity	NPC271734
0.7881	Intermediate Similarity	NPC90723
0.7881	Intermediate Similarity	NPC317105
0.7881	Intermediate Similarity	NPC162799
0.7867	Intermediate Similarity	NPC470204
0.7867	Intermediate Similarity	NPC122141
0.7852	Intermediate Similarity	NPC299594
0.7838	Intermediate Similarity	NPC80597
0.7838	Intermediate Similarity	NPC34844
0.7838	Intermediate Similarity	NPC75540
0.7838	Intermediate Similarity	NPC212376
0.7838	Intermediate Similarity	NPC70922
0.7838	Intermediate Similarity	NPC207726
0.7838	Intermediate Similarity	NPC211572
0.782	Intermediate Similarity	NPC46358
0.7815	Intermediate Similarity	NPC470203
0.7793	Intermediate Similarity	NPC316069
0.7785	Intermediate Similarity	NPC469785
0.7778	Intermediate Similarity	NPC476140
0.777	Intermediate Similarity	NPC232798
0.777	Intermediate Similarity	NPC161108
0.7748	Intermediate Similarity	NPC279918
0.7746	Intermediate Similarity	NPC104483
0.774	Intermediate Similarity	NPC114209
0.7733	Intermediate Similarity	NPC469762
0.773	Intermediate Similarity	NPC314102
0.773	Intermediate Similarity	NPC251722
0.773	Intermediate Similarity	NPC150259
0.7727	Intermediate Similarity	NPC201700
0.7727	Intermediate Similarity	NPC63751
0.7727	Intermediate Similarity	NPC154293
0.7718	Intermediate Similarity	NPC476297
0.7718	Intermediate Similarity	NPC476219
0.7712	Intermediate Similarity	NPC274229
0.7712	Intermediate Similarity	NPC115232
0.7697	Intermediate Similarity	NPC282231
0.7682	Intermediate Similarity	NPC67056
0.7682	Intermediate Similarity	NPC230869
0.768	Intermediate Similarity	NPC302790
0.7677	Intermediate Similarity	NPC194411
0.7677	Intermediate Similarity	NPC474897
0.7677	Intermediate Similarity	NPC280548
0.7647	Intermediate Similarity	NPC8104
0.7647	Intermediate Similarity	NPC472587
0.7647	Intermediate Similarity	NPC21174
0.7647	Intermediate Similarity	NPC271797
0.7647	Intermediate Similarity	NPC247987
0.7632	Intermediate Similarity	NPC131718
0.7628	Intermediate Similarity	NPC6982
0.761	Intermediate Similarity	NPC88363
0.7597	Intermediate Similarity	NPC280864
0.7597	Intermediate Similarity	NPC17751
0.7586	Intermediate Similarity	NPC20144
0.7582	Intermediate Similarity	NPC214106
0.758	Intermediate Similarity	NPC97525
0.758	Intermediate Similarity	NPC34508
0.758	Intermediate Similarity	NPC477611
0.758	Intermediate Similarity	NPC474409
0.7564	Intermediate Similarity	NPC97343
0.7551	Intermediate Similarity	NPC478186
0.7548	Intermediate Similarity	NPC49954
0.7548	Intermediate Similarity	NPC474561
0.7548	Intermediate Similarity	NPC54988
0.7532	Intermediate Similarity	NPC189812
0.7532	Intermediate Similarity	NPC275305
0.7532	Intermediate Similarity	NPC329688
0.7532	Intermediate Similarity	NPC37423
0.7532	Intermediate Similarity	NPC311276
0.7532	Intermediate Similarity	NPC40779
0.7532	Intermediate Similarity	NPC194640
0.7532	Intermediate Similarity	NPC102423
0.7516	Intermediate Similarity	NPC82331
0.75	Intermediate Similarity	NPC470111
0.75	Intermediate Similarity	NPC317430
0.7484	Intermediate Similarity	NPC280852
0.7484	Intermediate Similarity	NPC288785
0.7484	Intermediate Similarity	NPC470508
0.7469	Intermediate Similarity	NPC212535
0.7468	Intermediate Similarity	NPC252572
0.7452	Intermediate Similarity	NPC471943
0.7448	Intermediate Similarity	NPC238499
0.7444	Intermediate Similarity	NPC91958
0.7438	Intermediate Similarity	NPC284775
0.7438	Intermediate Similarity	NPC59269
0.7438	Intermediate Similarity	NPC68354
0.7438	Intermediate Similarity	NPC151939
0.7436	Intermediate Similarity	NPC470509
0.7436	Intermediate Similarity	NPC109447
0.7436	Intermediate Similarity	NPC160105
0.7436	Intermediate Similarity	NPC49217
0.7429	Intermediate Similarity	NPC282398

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 NPC473762 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	548
0.1-0.2	877
0.2-0.3	1025
0.3-0.4	2168
0.4-0.5	2393
0.5-0.6	1507
0.6-0.7	523
0.7-0.8	88
0.8-0.85	14
0.85-0.9	6
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9084	High Similarity	NPD1262	Discovery
0.8963	High Similarity	NPD5254	Discontinued
0.8881	High Similarity	NPD3943	Clinical (unspecified phase)
0.8722	High Similarity	NPD198	Clinical (unspecified phase)
0.8561	High Similarity	NPD1528	Clinical (unspecified phase)
0.854	High Similarity	NPD1722	Approved
0.8529	High Similarity	NPD786	Approved
0.8507	High Similarity	NPD4880	Discontinued
0.844	Intermediate Similarity	NPD3100	Discontinued
0.844	Intermediate Similarity	NPD4374	Clinical (unspecified phase)
0.8409	Intermediate Similarity	NPD947	Approved
0.838	Intermediate Similarity	NPD4463	Approved
0.838	Intermediate Similarity	NPD4462	Approved
0.8345	Intermediate Similarity	NPD4637	Clinical (unspecified phase)
0.8298	Intermediate Similarity	NPD1683	Approved
0.8296	Intermediate Similarity	NPD3385	Approved
0.8252	Intermediate Similarity	NPD2172	Phase 1
0.8148	Intermediate Similarity	NPD1251	Discontinued
0.8138	Intermediate Similarity	NPD2837	Discontinued
0.8134	Intermediate Similarity	NPD3654	Approved
0.8043	Intermediate Similarity	NPD1254	Approved
0.8043	Intermediate Similarity	NPD1253	Approved
0.8043	Intermediate Similarity	NPD1255	Approved
0.8043	Intermediate Similarity	NPD1256	Approved
0.8	Intermediate Similarity	NPD3323	Discontinued
0.7933	Intermediate Similarity	NPD972	Clinical (unspecified phase)
0.7887	Intermediate Similarity	NPD1592	Phase 3
0.7877	Intermediate Similarity	NPD3833	Phase 3
0.7877	Intermediate Similarity	NPD3835	Phase 3
0.7867	Intermediate Similarity	NPD1403	Approved
0.7867	Intermediate Similarity	NPD1404	Approved
0.7857	Intermediate Similarity	NPD6554	Approved
0.7857	Intermediate Similarity	NPD45	Approved
0.7829	Intermediate Similarity	NPD5744	Clinical (unspecified phase)
0.7815	Intermediate Similarity	NPD1853	Clinical (unspecified phase)
0.7792	Intermediate Similarity	NPD1326	Approved
0.7792	Intermediate Similarity	NPD1325	Approved
0.7746	Intermediate Similarity	NPD680	Discontinued
0.774	Intermediate Similarity	NPD4547	Phase 3
0.7727	Intermediate Similarity	NPD2641	Approved
0.7727	Intermediate Similarity	NPD2640	Approved
0.7727	Intermediate Similarity	NPD5069	Clinical (unspecified phase)
0.7662	Intermediate Similarity	NPD2639	Approved
0.7662	Intermediate Similarity	NPD2642	Approved
0.7658	Intermediate Similarity	NPD6203	Clinical (unspecified phase)
0.7628	Intermediate Similarity	NPD3609	Approved
0.7628	Intermediate Similarity	NPD3610	Approved
0.7613	Intermediate Similarity	NPD5021	Discontinued
0.7613	Intermediate Similarity	NPD2185	Clinical (unspecified phase)
0.7591	Intermediate Similarity	NPD992	Clinical (unspecified phase)
0.7591	Intermediate Similarity	NPD991	Phase 2
0.758	Intermediate Similarity	NPD4112	Clinical (unspecified phase)
0.7532	Intermediate Similarity	NPD5065	Approved
0.7532	Intermediate Similarity	NPD4128	Approved
0.7484	Intermediate Similarity	NPD4075	Phase 2
0.7481	Intermediate Similarity	NPD1561	Phase 2
0.7469	Intermediate Similarity	NPD5105	Approved
0.7469	Intermediate Similarity	NPD5106	Approved
0.7466	Intermediate Similarity	NPD2006	Phase 2
0.7453	Intermediate Similarity	NPD5473	Discontinued
0.745	Intermediate Similarity	NPD2430	Phase 2
0.7438	Intermediate Similarity	NPD4181	Approved
0.7438	Intermediate Similarity	NPD3506	Approved
0.7438	Intermediate Similarity	NPD3505	Approved
0.7434	Intermediate Similarity	NPD2150	Discontinued
0.7429	Intermediate Similarity	NPD3475	Approved
0.7429	Intermediate Similarity	NPD3476	Approved
0.7415	Intermediate Similarity	NPD4509	Discontinued
0.7415	Intermediate Similarity	NPD3401	Clinical (unspecified phase)
0.7397	Intermediate Similarity	NPD3834	Clinical (unspecified phase)
0.7391	Intermediate Similarity	NPD4079	Approved
0.7391	Intermediate Similarity	NPD8386	Phase 2
0.7391	Intermediate Similarity	NPD4076	Approved
0.7386	Intermediate Similarity	NPD1192	Clinical (unspecified phase)
0.7381	Intermediate Similarity	NPD990	Approved
0.7381	Intermediate Similarity	NPD993	Approved
0.7378	Intermediate Similarity	NPD6610	Clinical (unspecified phase)
0.7347	Intermediate Similarity	NPD4047	Discontinued
0.7346	Intermediate Similarity	NPD6277	Clinical (unspecified phase)
0.7346	Intermediate Similarity	NPD6595	Phase 3
0.7346	Intermediate Similarity	NPD8464	Clinical (unspecified phase)
0.7346	Intermediate Similarity	NPD702	Clinical (unspecified phase)
0.7342	Intermediate Similarity	NPD4184	Clinical (unspecified phase)
0.7342	Intermediate Similarity	NPD5436	Phase 1
0.7338	Intermediate Similarity	NPD2118	Approved
0.7338	Intermediate Similarity	NPD2119	Approved
0.7329	Intermediate Similarity	NPD2144	Approved
0.732	Intermediate Similarity	NPD2580	Discontinued
0.7317	Intermediate Similarity	NPD3607	Clinical (unspecified phase)
0.7301	Intermediate Similarity	NPD1707	Approved
0.7301	Intermediate Similarity	NPD1708	Approved
0.7301	Intermediate Similarity	NPD1895	Discontinued
0.7296	Intermediate Similarity	NPD6828	Phase 2
0.7296	Intermediate Similarity	NPD6827	Clinical (unspecified phase)
0.7289	Intermediate Similarity	NPD8431	Approved
0.7278	Intermediate Similarity	NPD4779	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD4326	Phase 2
0.7256	Intermediate Similarity	NPD3319	Phase 1
0.7256	Intermediate Similarity	NPD3318	Approved
0.7256	Intermediate Similarity	NPD3320	Approved
0.7255	Intermediate Similarity	NPD1597	Phase 1
0.7237	Intermediate Similarity	NPD2882	Phase 1
0.723	Intermediate Similarity	NPD2007	Clinical (unspecified phase)
0.7226	Intermediate Similarity	NPD1554	Clinical (unspecified phase)
0.7219	Intermediate Similarity	NPD5538	Clinical (unspecified phase)
0.7205	Intermediate Similarity	NPD482	Approved
0.7195	Intermediate Similarity	NPD3038	Discontinued
0.716	Intermediate Similarity	NPD749	Clinical (unspecified phase)
0.7153	Intermediate Similarity	NPD4030	Approved
0.7153	Intermediate Similarity	NPD4028	Approved
0.7153	Intermediate Similarity	NPD4029	Approved
0.7143	Intermediate Similarity	NPD9583	Approved
0.7134	Intermediate Similarity	NPD5315	Discontinued
0.7126	Intermediate Similarity	NPD6217	Discontinued
0.7126	Intermediate Similarity	NPD4426	Clinical (unspecified phase)
0.7124	Intermediate Similarity	NPD6476	Clinical (unspecified phase)
0.7124	Intermediate Similarity	NPD6158	Phase 2
0.7107	Intermediate Similarity	NPD1248	Discontinued
0.7101	Intermediate Similarity	NPD5787	Discontinued
0.7097	Intermediate Similarity	NPD473	Clinical (unspecified phase)
0.7089	Intermediate Similarity	NPD5140	Approved
0.7089	Intermediate Similarity	NPD5138	Approved
0.7083	Intermediate Similarity	NPD5590	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD3961	Discontinued
0.7083	Intermediate Similarity	NPD3486	Clinical (unspecified phase)
0.708	Intermediate Similarity	NPD4811	Discontinued
0.7073	Intermediate Similarity	NPD6448	Phase 1
0.7067	Intermediate Similarity	NPD1918	Clinical (unspecified phase)
0.7063	Intermediate Similarity	NPD715	Phase 3
0.7059	Intermediate Similarity	NPD6630	Clinical (unspecified phase)
0.7051	Intermediate Similarity	NPD2330	Approved
0.7051	Intermediate Similarity	NPD2865	Clinical (unspecified phase)
0.7048	Intermediate Similarity	NPD1332	Clinical (unspecified phase)
0.7048	Intermediate Similarity	NPD5728	Clinical (unspecified phase)
0.7044	Intermediate Similarity	NPD4550	Clinical (unspecified phase)
0.7041	Intermediate Similarity	NPD8110	Clinical (unspecified phase)
0.7041	Intermediate Similarity	NPD1534	Approved
0.7034	Intermediate Similarity	NPD3942	Approved
0.7034	Intermediate Similarity	NPD3944	Approved
0.7032	Intermediate Similarity	NPD976	Approved
0.7032	Intermediate Similarity	NPD977	Approved
0.7032	Intermediate Similarity	NPD2165	Phase 1
0.7032	Intermediate Similarity	NPD975	Approved
0.7029	Intermediate Similarity	NPD268	Approved
0.7029	Intermediate Similarity	NPD271	Approved
0.7029	Intermediate Similarity	NPD270	Clinical (unspecified phase)
0.7027	Intermediate Similarity	NPD768	Clinical (unspecified phase)
0.7025	Intermediate Similarity	NPD2385	Clinical (unspecified phase)
0.7012	Intermediate Similarity	NPD4398	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD9357	Approved
0.7	Intermediate Similarity	NPD2392	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD5145	Clinical (unspecified phase)
0.6994	Remote Similarity	NPD3799	Suspended
0.6987	Remote Similarity	NPD2927	Phase 3
0.6987	Remote Similarity	NPD3114	Approved
0.6987	Remote Similarity	NPD3115	Approved
0.6987	Remote Similarity	NPD3113	Approved
0.6987	Remote Similarity	NPD3112	Approved
0.6987	Remote Similarity	NPD2748	Clinical (unspecified phase)
0.6982	Remote Similarity	NPD2310	Clinical (unspecified phase)
0.6982	Remote Similarity	NPD6141	Clinical (unspecified phase)
0.6972	Remote Similarity	NPD1598	Discontinued
0.6959	Remote Similarity	NPD5912	Clinical (unspecified phase)
0.6959	Remote Similarity	NPD6180	Clinical (unspecified phase)
0.6959	Remote Similarity	NPD5913	Phase 3
0.6957	Remote Similarity	NPD4640	Approved
0.6957	Remote Similarity	NPD4639	Approved
0.6957	Remote Similarity	NPD4638	Approved
0.6957	Remote Similarity	NPD2844	Phase 3
0.6946	Remote Similarity	NPD2092	Phase 2
0.6946	Remote Similarity	NPD2095	Phase 2
0.6946	Remote Similarity	NPD2094	Phase 2
0.6937	Remote Similarity	NPD2719	Clinical (unspecified phase)
0.6937	Remote Similarity	NPD2720	Phase 1
0.6936	Remote Similarity	NPD3791	Clinical (unspecified phase)
0.6933	Remote Similarity	NPD5020	Approved
0.6928	Remote Similarity	NPD5962	Phase 2
0.6923	Remote Similarity	NPD6285	Phase 2
0.6905	Remote Similarity	NPD2091	Phase 2
0.6905	Remote Similarity	NPD2096	Phase 2
0.6901	Remote Similarity	NPD4499	Approved
0.6897	Remote Similarity	NPD2960	Clinical (unspecified phase)
0.6897	Remote Similarity	NPD6449	Clinical (unspecified phase)
0.6886	Remote Similarity	NPD4649	Clinical (unspecified phase)
0.6886	Remote Similarity	NPD4399	Phase 2
0.6883	Remote Similarity	NPD3852	Clinical (unspecified phase)
0.6879	Remote Similarity	NPD5575	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD6451	Discontinued
0.6875	Remote Similarity	NPD404	Discontinued
0.6871	Remote Similarity	NPD1567	Clinical (unspecified phase)
0.6864	Remote Similarity	NPD1227	Phase 2
0.6861	Remote Similarity	NPD9392	Approved
0.6861	Remote Similarity	NPD9396	Approved
0.6855	Remote Similarity	NPD6074	Clinical (unspecified phase)
0.6848	Remote Similarity	NPD2382	Approved
0.6848	Remote Similarity	NPD2380	Approved
0.6848	Remote Similarity	NPD2381	Approved
0.6839	Remote Similarity	NPD7618	Phase 3
0.6839	Remote Similarity	NPD7619	Phase 3
0.6838	Remote Similarity	NPD269	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