NPASS Compound

Structure

NPC271734 OpenBabel07101719132D 29 31 0 0 0 0 0 0 0 0999 V2000 3.9811 4.9635 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1835 -2.8512 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.9156 -2.8512 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6150 4.5975 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6150 3.5975 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9811 4.9635 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0495 -1.3512 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1835 -0.8512 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0495 0.6488 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0495 1.6488 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3175 0.6488 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5962 2.1100 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0495 -2.3512 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1835 0.1488 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3175 1.6488 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5743 2.3179 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1835 2.1488 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2872 1.1590 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9811 3.2315 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3090 0.9511 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6473 -0.5352 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6691 -0.7431 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4811 4.0975 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9756 3.1270 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 1.9563 0.4158 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -0.3601 1.6942 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.3164 -1.2784 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.3601 -1.6942 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 6 2 0 0 0 0 2 13 1 0 0 0 0 3 13 1 0 0 0 0 4 23 1 0 0 0 0 5 23 1 0 0 0 0 6 23 1 0 0 0 0 7 8 1 0 0 0 0 7 13 2 0 0 0 0 8 14 1 0 0 0 0 9 10 2 0 0 0 0 9 14 1 0 0 0 0 10 17 1 0 0 0 0 11 14 2 0 0 0 0 11 15 1 0 0 0 0 12 16 1 0 0 0 0 12 18 2 0 0 0 0 15 16 1 0 0 0 0 15 17 2 0 0 0 0 16 19 2 0 0 0 0 17 24 1 0 0 0 0 18 20 1 0 0 0 0 18 25 1 0 0 0 0 19 23 1 0 0 0 0 19 24 1 0 0 0 0 20 26 2 0 0 0 0 20 27 1 0 0 0 0 21 22 1 0 0 0 0 21 25 1 0 0 0 0 21 28 2 0 0 0 0 22 26 1 0 0 0 0 22 29 2 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	391.19
Volume:	413.691
LogP:	4.411
LogD:	2.971
LogS:	-4.671
# Rotatable Bonds:	6
TPSA:	91.39
# H-Bond Aceptor:	6
# H-Bond Donor:	2
# Rings:	3
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.45
Synthetic Accessibility Score:	3.532
Fsp3:	0.304
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
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:	-4.829
MDCK Permeability:	1.6478619727422483e-05
Pgp-inhibitor:	0.997
Pgp-substrate:	0.022
Human Intestinal Absorption (HIA):	0.01
20% Bioavailability (F20%):	0.797
30% Bioavailability (F30%):	0.013

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.114
Plasma Protein Binding (PPB):	94.8913345336914%
Volume Distribution (VD):	0.517
Pgp-substrate:	1.9921034574508667%

ADMET: Metabolism

CYP1A2-inhibitor:	0.583
CYP1A2-substrate:	0.089
CYP2C19-inhibitor:	0.582
CYP2C19-substrate:	0.23
CYP2C9-inhibitor:	0.538
CYP2C9-substrate:	0.954
CYP2D6-inhibitor:	0.14
CYP2D6-substrate:	0.449
CYP3A4-inhibitor:	0.712
CYP3A4-substrate:	0.298

ADMET: Excretion

Clearance (CL):	1.358
Half-life (T1/2):	0.68

ADMET: Toxicity

hERG Blockers:	0.014
Human Hepatotoxicity (H-HT):	0.665
Drug-inuced Liver Injury (DILI):	0.945
AMES Toxicity:	0.063
Rat Oral Acute Toxicity:	0.868
Maximum Recommended Daily Dose:	0.287
Skin Sensitization:	0.198
Carcinogencity:	0.281
Eye Corrosion:	0.003
Eye Irritation:	0.01
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: NPC271734

Natural Product ID:	NPC271734
*Common Name:**	Variecolorin J
IUPAC Name:	(6Z)-6-[[2-(2-methylbut-3-en-2-yl)-5-(3-methylbut-2-enyl)-1H-indol-3-yl]methylidene]piperazine-2,3,5-trione
Synonyms:	Variecolorin J
Standard InCHIKey:	DNBYIRPIGWYFFR-PDGQHHTCSA-N
Standard InCHI:	InChI=1S/C23H25N3O3/c1-6-23(4,5)19-16(12-18-20(27)26-22(29)21(28)25-18)15-11-14(8-7-13(2)3)9-10-17(15)24-19/h6-7,9-12,24H,1,8H2,2-5H3,(H,25,28)(H,26,27,29)/b18-12-
SMILES:	C=CC(c1[nH]c2c(c1/C=C/1NC(=O)C(=O)N=C1O)cc(cc2)CC=C(C)C)(C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL251226
PubChem CID:	23655531
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000264] Organic acids and derivatives [CHEMONTID:0000265] Carboxylic acids and derivatives [CHEMONTID:0000013] Amino acids, peptides, and analogues [CHEMONTID:0000347] Amino acids and derivatives [CHEMONTID:0000060] Alpha amino acids and derivatives

*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
NPO31540	Aspergillus variecolor	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1021/jo00010a040]
NPO31540	Aspergillus variecolor	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17896816]
NPO31540	Aspergillus variecolor	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17965475]

☑ 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	5

Activity Type	# Activity
Cell Line	3
NON-MOLECULAR	1
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT168	Cell Line	P388	Mus musculus	IC50	>	50000.0	nM	PMID[495158]
NPT116	Cell Line	HL-60	Homo sapiens	IC50	>	50000.0	nM	PMID[495158]
NPT181	Cell Line	Bel-7402	Homo sapiens	IC50	>	50000.0	nM	PMID[495158]
NPT35	Others	n.a.		IC50	=	102000.0	nM	PMID[495158]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	>	50000.0	nM	PMID[495158]

☑ 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 NPC271734 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	473
0.1-0.2	4052
0.2-0.3	18097
0.3-0.4	13464
0.4-0.5	2910
0.5-0.6	2085
0.6-0.7	1342
0.7-0.8	245
0.8-0.85	18
0.85-0.9	8
0.9-0.95	1
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9732	High Similarity	NPC299594
0.9329	High Similarity	NPC124005
0.9085	High Similarity	NPC38736
0.9067	High Similarity	NPC129042
0.906	High Similarity	NPC242556
0.9026	High Similarity	NPC184476
0.8854	High Similarity	NPC473320
0.8824	High Similarity	NPC37548
0.8824	High Similarity	NPC187951
0.8704	High Similarity	NPC6982
0.8634	High Similarity	NPC470509
0.8599	High Similarity	NPC471458
0.8599	High Similarity	NPC470507
0.8509	High Similarity	NPC472587
0.8447	Intermediate Similarity	NPC16667
0.8424	Intermediate Similarity	NPC34508
0.8323	Intermediate Similarity	NPC288785
0.8269	Intermediate Similarity	NPC470440
0.8225	Intermediate Similarity	NPC270009
0.821	Intermediate Similarity	NPC67056
0.8199	Intermediate Similarity	NPC285469
0.8193	Intermediate Similarity	NPC280548
0.8176	Intermediate Similarity	NPC91179
0.8137	Intermediate Similarity	NPC207726
0.8129	Intermediate Similarity	NPC192270
0.8118	Intermediate Similarity	NPC11126
0.8079	Intermediate Similarity	NPC475450
0.8079	Intermediate Similarity	NPC179365
0.8035	Intermediate Similarity	NPC228835
0.8013	Intermediate Similarity	NPC22079
0.8012	Intermediate Similarity	NPC470508
0.7975	Intermediate Similarity	NPC141353
0.795	Intermediate Similarity	NPC24678
0.795	Intermediate Similarity	NPC105818
0.7947	Intermediate Similarity	NPC473587
0.7931	Intermediate Similarity	NPC165495
0.7895	Intermediate Similarity	NPC475428
0.7882	Intermediate Similarity	NPC161861
0.7881	Intermediate Similarity	NPC473762
0.7853	Intermediate Similarity	NPC46413
0.7849	Intermediate Similarity	NPC293472
0.7841	Intermediate Similarity	NPC94752
0.7812	Intermediate Similarity	NPC159856
0.7806	Intermediate Similarity	NPC198988
0.7803	Intermediate Similarity	NPC472443
0.7797	Intermediate Similarity	NPC17059
0.7792	Intermediate Similarity	NPC473930
0.7785	Intermediate Similarity	NPC2949
0.7756	Intermediate Similarity	NPC325252
0.7748	Intermediate Similarity	NPC250361
0.7744	Intermediate Similarity	NPC281094
0.7718	Intermediate Similarity	NPC41174
0.7702	Intermediate Similarity	NPC314372
0.7688	Intermediate Similarity	NPC190296
0.767	Intermediate Similarity	NPC472444
0.7665	Intermediate Similarity	NPC92796
0.7665	Intermediate Similarity	NPC135141
0.7654	Intermediate Similarity	NPC478186
0.7647	Intermediate Similarity	NPC474561
0.7647	Intermediate Similarity	NPC49954
0.7643	Intermediate Similarity	NPC218268
0.7637	Intermediate Similarity	NPC294693
0.7633	Intermediate Similarity	NPC194640
0.7622	Intermediate Similarity	NPC33421
0.7616	Intermediate Similarity	NPC470498
0.761	Intermediate Similarity	NPC88097
0.7607	Intermediate Similarity	NPC477134
0.76	Intermediate Similarity	NPC219336
0.76	Intermediate Similarity	NPC215795
0.76	Intermediate Similarity	NPC176199
0.7574	Intermediate Similarity	NPC282231
0.7562	Intermediate Similarity	NPC59084
0.7562	Intermediate Similarity	NPC115611
0.7562	Intermediate Similarity	NPC238499
0.7558	Intermediate Similarity	NPC194411
0.7558	Intermediate Similarity	NPC471943
0.7556	Intermediate Similarity	NPC213629
0.7543	Intermediate Similarity	NPC68354
0.7543	Intermediate Similarity	NPC15573
0.7543	Intermediate Similarity	NPC217372
0.7543	Intermediate Similarity	NPC183662
0.753	Intermediate Similarity	NPC73952
0.753	Intermediate Similarity	NPC469765
0.753	Intermediate Similarity	NPC25008
0.753	Intermediate Similarity	NPC259644
0.753	Intermediate Similarity	NPC469763
0.753	Intermediate Similarity	NPC469786
0.753	Intermediate Similarity	NPC469760
0.7529	Intermediate Similarity	NPC472586
0.7529	Intermediate Similarity	NPC271797
0.7529	Intermediate Similarity	NPC21174
0.7516	Intermediate Similarity	NPC277157
0.7516	Intermediate Similarity	NPC63157
0.7516	Intermediate Similarity	NPC473868
0.7515	Intermediate Similarity	NPC279918
0.7514	Intermediate Similarity	NPC470499
0.75	Intermediate Similarity	NPC76982
0.75	Intermediate Similarity	NPC63751
0.75	Intermediate Similarity	NPC312092
0.75	Intermediate Similarity	NPC21605
0.75	Intermediate Similarity	NPC154293
0.7486	Intermediate Similarity	NPC151635
0.7486	Intermediate Similarity	NPC133003
0.7485	Intermediate Similarity	NPC75540
0.7485	Intermediate Similarity	NPC212376
0.7485	Intermediate Similarity	NPC70922
0.7485	Intermediate Similarity	NPC115232
0.7485	Intermediate Similarity	NPC211572
0.7485	Intermediate Similarity	NPC80597
0.7473	Intermediate Similarity	NPC32200
0.7473	Intermediate Similarity	NPC243716
0.7459	Intermediate Similarity	NPC221873
0.7458	Intermediate Similarity	NPC198339
0.7458	Intermediate Similarity	NPC469896
0.7453	Intermediate Similarity	NPC469783
0.7453	Intermediate Similarity	NPC469784
0.7453	Intermediate Similarity	NPC469780
0.7453	Intermediate Similarity	NPC469768
0.7453	Intermediate Similarity	NPC469767
0.7453	Intermediate Similarity	NPC469779
0.7453	Intermediate Similarity	NPC469761
0.7442	Intermediate Similarity	NPC49217
0.7429	Intermediate Similarity	NPC275305
0.7429	Intermediate Similarity	NPC37423
0.7427	Intermediate Similarity	NPC476118
0.7427	Intermediate Similarity	NPC8104
0.7425	Intermediate Similarity	NPC200214
0.7407	Intermediate Similarity	NPC469766
0.7403	Intermediate Similarity	NPC317030
0.7401	Intermediate Similarity	NPC213468
0.7399	Intermediate Similarity	NPC201700
0.7396	Intermediate Similarity	NPC469762
0.7394	Intermediate Similarity	NPC471944
0.7394	Intermediate Similarity	NPC471957
0.7391	Intermediate Similarity	NPC73767
0.7389	Intermediate Similarity	NPC476319
0.7378	Intermediate Similarity	NPC204141
0.7375	Intermediate Similarity	NPC84911
0.7375	Intermediate Similarity	NPC125746
0.7368	Intermediate Similarity	NPC194881
0.7366	Intermediate Similarity	NPC232130
0.7362	Intermediate Similarity	NPC20144
0.736	Intermediate Similarity	NPC16659
0.736	Intermediate Similarity	NPC88110
0.7356	Intermediate Similarity	NPC65080
0.7353	Intermediate Similarity	NPC206819
0.7353	Intermediate Similarity	NPC475990
0.7353	Intermediate Similarity	NPC318065
0.7351	Intermediate Similarity	NPC133366
0.7351	Intermediate Similarity	NPC215519
0.7349	Intermediate Similarity	NPC2272
0.7346	Intermediate Similarity	NPC284635
0.7345	Intermediate Similarity	NPC248454
0.7341	Intermediate Similarity	NPC54988
0.7341	Intermediate Similarity	NPC160105
0.7341	Intermediate Similarity	NPC109447
0.734	Intermediate Similarity	NPC470497
0.7337	Intermediate Similarity	NPC469785
0.7333	Intermediate Similarity	NPC190007
0.7326	Intermediate Similarity	NPC171317
0.7326	Intermediate Similarity	NPC311276
0.7326	Intermediate Similarity	NPC478182
0.7322	Intermediate Similarity	NPC324091
0.7322	Intermediate Similarity	NPC206967
0.7318	Intermediate Similarity	NPC314394
0.7312	Intermediate Similarity	NPC261195
0.7312	Intermediate Similarity	NPC29886
0.7312	Intermediate Similarity	NPC96102
0.731	Intermediate Similarity	NPC131718
0.7308	Intermediate Similarity	NPC204565
0.7303	Intermediate Similarity	NPC126709
0.7303	Intermediate Similarity	NPC248041
0.7303	Intermediate Similarity	NPC88363
0.7303	Intermediate Similarity	NPC265710
0.7302	Intermediate Similarity	NPC300183
0.7299	Intermediate Similarity	NPC317430
0.7297	Intermediate Similarity	NPC474177
0.7294	Intermediate Similarity	NPC286427
0.7293	Intermediate Similarity	NPC94943
0.7293	Intermediate Similarity	NPC99939
0.7293	Intermediate Similarity	NPC308931
0.7289	Intermediate Similarity	NPC179787
0.7289	Intermediate Similarity	NPC201380
0.7284	Intermediate Similarity	NPC110126
0.7284	Intermediate Similarity	NPC104483
0.7278	Intermediate Similarity	NPC470205
0.7273	Intermediate Similarity	NPC141454
0.7273	Intermediate Similarity	NPC97525
0.7273	Intermediate Similarity	NPC472123
0.7273	Intermediate Similarity	NPC122718
0.7268	Intermediate Similarity	NPC173028
0.7268	Intermediate Similarity	NPC65215
0.7267	Intermediate Similarity	NPC105127
0.7267	Intermediate Similarity	NPC214106
0.7251	Intermediate Similarity	NPC41257
0.7247	Intermediate Similarity	NPC240088
0.7247	Intermediate Similarity	NPC59269
0.7247	Intermediate Similarity	NPC473380
0.7247	Intermediate Similarity	NPC145885
0.7247	Intermediate Similarity	NPC14113

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 NPC271734 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	270
0.1-0.2	643
0.2-0.3	974
0.3-0.4	1807
0.4-0.5	2589
0.5-0.6	2236
0.6-0.7	556
0.7-0.8	74
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8176	Intermediate Similarity	NPD4462	Approved
0.8176	Intermediate Similarity	NPD4463	Approved
0.8103	Intermediate Similarity	NPD3961	Discontinued
0.7904	Intermediate Similarity	NPD5744	Clinical (unspecified phase)
0.7898	Intermediate Similarity	NPD6141	Clinical (unspecified phase)
0.7888	Intermediate Similarity	NPD3100	Discontinued
0.7765	Intermediate Similarity	NPD1325	Approved
0.7765	Intermediate Similarity	NPD1326	Approved
0.773	Intermediate Similarity	NPD2172	Phase 1
0.7706	Intermediate Similarity	NPD5069	Clinical (unspecified phase)
0.7692	Intermediate Similarity	NPD2915	Discontinued
0.7692	Intermediate Similarity	NPD6449	Clinical (unspecified phase)
0.7688	Intermediate Similarity	NPD4075	Phase 2
0.764	Intermediate Similarity	NPD5254	Discontinued
0.7625	Intermediate Similarity	NPD1592	Phase 3
0.7602	Intermediate Similarity	NPD5021	Discontinued
0.7586	Intermediate Similarity	NPD5104	Approved
0.7572	Intermediate Similarity	NPD4112	Clinical (unspecified phase)
0.7562	Intermediate Similarity	NPD3943	Clinical (unspecified phase)
0.7546	Intermediate Similarity	NPD1683	Approved
0.7543	Intermediate Similarity	NPD3506	Approved
0.7543	Intermediate Similarity	NPD3505	Approved
0.7541	Intermediate Similarity	NPD7618	Phase 3
0.7541	Intermediate Similarity	NPD7619	Phase 3
0.7529	Intermediate Similarity	NPD4128	Approved
0.7515	Intermediate Similarity	NPD3833	Phase 3
0.7515	Intermediate Similarity	NPD3835	Phase 3
0.75	Intermediate Similarity	NPD4079	Approved
0.75	Intermediate Similarity	NPD4326	Phase 2
0.75	Intermediate Similarity	NPD8386	Phase 2
0.75	Intermediate Similarity	NPD4076	Approved
0.7443	Intermediate Similarity	NPD2144	Approved
0.7427	Intermediate Similarity	NPD5140	Approved
0.7427	Intermediate Similarity	NPD5138	Approved
0.7403	Intermediate Similarity	NPD3486	Clinical (unspecified phase)
0.7391	Intermediate Similarity	NPD786	Approved
0.7377	Intermediate Similarity	NPD6630	Clinical (unspecified phase)
0.7375	Intermediate Similarity	NPD1262	Discovery
0.7363	Intermediate Similarity	NPD6965	Clinical (unspecified phase)
0.7362	Intermediate Similarity	NPD4637	Clinical (unspecified phase)
0.7349	Intermediate Similarity	NPD4374	Clinical (unspecified phase)
0.7318	Intermediate Similarity	NPD3038	Discontinued
0.7312	Intermediate Similarity	NPD198	Clinical (unspecified phase)
0.731	Intermediate Similarity	NPD1404	Approved
0.731	Intermediate Similarity	NPD1403	Approved
0.7301	Intermediate Similarity	NPD1722	Approved
0.7301	Intermediate Similarity	NPD5020	Approved
0.7301	Intermediate Similarity	NPD3834	Clinical (unspecified phase)
0.7299	Intermediate Similarity	NPD2641	Approved
0.7299	Intermediate Similarity	NPD2640	Approved
0.7299	Intermediate Similarity	NPD2844	Phase 3
0.7293	Intermediate Similarity	NPD5075	Discontinued
0.7262	Intermediate Similarity	NPD2882	Phase 1
0.7257	Intermediate Similarity	NPD4184	Clinical (unspecified phase)
0.7247	Intermediate Similarity	NPD6203	Clinical (unspecified phase)
0.7247	Intermediate Similarity	NPD4181	Approved
0.7241	Intermediate Similarity	NPD2639	Approved
0.7241	Intermediate Similarity	NPD2642	Approved
0.7232	Intermediate Similarity	NPD5065	Approved
0.72	Intermediate Similarity	NPD2185	Clinical (unspecified phase)
0.7198	Intermediate Similarity	NPD6610	Clinical (unspecified phase)
0.7196	Intermediate Similarity	NPD6249	Phase 2
0.7196	Intermediate Similarity	NPD7621	Clinical (unspecified phase)
0.7196	Intermediate Similarity	NPD6248	Phase 2
0.7191	Intermediate Similarity	NPD749	Clinical (unspecified phase)
0.7189	Intermediate Similarity	NPD5592	Clinical (unspecified phase)
0.7184	Intermediate Similarity	NPD2719	Clinical (unspecified phase)
0.7184	Intermediate Similarity	NPD2720	Phase 1
0.7182	Intermediate Similarity	NPD5728	Clinical (unspecified phase)
0.7168	Intermediate Similarity	NPD972	Clinical (unspecified phase)
0.7158	Intermediate Similarity	NPD6217	Discontinued
0.7152	Intermediate Similarity	NPD3654	Approved
0.7143	Intermediate Similarity	NPD3607	Clinical (unspecified phase)
0.7135	Intermediate Similarity	NPD4499	Approved
0.7135	Intermediate Similarity	NPD482	Approved
0.712	Intermediate Similarity	NPD7903	Clinical (unspecified phase)
0.7111	Intermediate Similarity	NPD6448	Phase 1
0.7107	Intermediate Similarity	NPD8093	Discontinued
0.7102	Intermediate Similarity	NPD4638	Approved
0.7102	Intermediate Similarity	NPD4640	Approved
0.7102	Intermediate Similarity	NPD4639	Approved
0.7098	Intermediate Similarity	NPD5901	Discontinued
0.709	Intermediate Similarity	NPD6664	Approved
0.7088	Intermediate Similarity	NPD3320	Approved
0.7088	Intermediate Similarity	NPD2095	Phase 2
0.7088	Intermediate Similarity	NPD2094	Phase 2
0.7088	Intermediate Similarity	NPD3318	Approved
0.7088	Intermediate Similarity	NPD3319	Phase 1
0.7088	Intermediate Similarity	NPD2092	Phase 2
0.7081	Intermediate Similarity	NPD3385	Approved
0.7081	Intermediate Similarity	NPD4334	Discontinued
0.7074	Intermediate Similarity	NPD3791	Clinical (unspecified phase)
0.7072	Intermediate Similarity	NPD8464	Clinical (unspecified phase)
0.7072	Intermediate Similarity	NPD702	Clinical (unspecified phase)
0.7072	Intermediate Similarity	NPD6595	Phase 3
0.7065	Intermediate Similarity	NPD5820	Clinical (unspecified phase)
0.7065	Intermediate Similarity	NPD5809	Phase 3
0.7052	Intermediate Similarity	NPD1554	Clinical (unspecified phase)
0.7049	Intermediate Similarity	NPD2091	Phase 2
0.7049	Intermediate Similarity	NPD2096	Phase 2
0.7047	Intermediate Similarity	NPD5487	Phase 1
0.7045	Intermediate Similarity	NPD4554	Clinical (unspecified phase)
0.7044	Intermediate Similarity	NPD947	Approved
0.7037	Intermediate Similarity	NPD4880	Discontinued
0.7031	Intermediate Similarity	NPD4511	Phase 1
0.7029	Intermediate Similarity	NPD3583	Phase 2
0.7029	Intermediate Similarity	NPD3323	Discontinued
0.7027	Intermediate Similarity	NPD8431	Approved
0.7026	Intermediate Similarity	NPD8493	Clinical (unspecified phase)
0.7026	Intermediate Similarity	NPD8322	Phase 2
0.7026	Intermediate Similarity	NPD6838	Clinical (unspecified phase)
0.7018	Intermediate Similarity	NPD2837	Discontinued
0.7016	Intermediate Similarity	NPD3800	Clinical (unspecified phase)
0.701	Intermediate Similarity	NPD8272	Phase 2
0.7005	Intermediate Similarity	NPD6180	Clinical (unspecified phase)
0.7005	Intermediate Similarity	NPD3785	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD2380	Approved
0.7	Intermediate Similarity	NPD2381	Approved
0.7	Intermediate Similarity	NPD2382	Approved
0.6995	Remote Similarity	NPD5596	Phase 2
0.6982	Remote Similarity	NPD4547	Phase 3
0.6978	Remote Similarity	NPD5473	Discontinued
0.6978	Remote Similarity	NPD6452	Discontinued
0.6973	Remote Similarity	NPD7026	Phase 2
0.6973	Remote Similarity	NPD4426	Clinical (unspecified phase)
0.6959	Remote Similarity	NPD6476	Clinical (unspecified phase)
0.6959	Remote Similarity	NPD6158	Phase 2
0.6952	Remote Similarity	NPD2564	Approved
0.6952	Remote Similarity	NPD2565	Phase 2
0.6946	Remote Similarity	NPD4047	Discontinued
0.6936	Remote Similarity	NPD2580	Discontinued
0.6931	Remote Similarity	NPD8405	Clinical (unspecified phase)
0.6927	Remote Similarity	NPD7716	Approved
0.6927	Remote Similarity	NPD7717	Approved
0.6923	Remote Similarity	NPD1528	Clinical (unspecified phase)
0.6919	Remote Similarity	NPD7998	Clinical (unspecified phase)
0.6911	Remote Similarity	NPD6206	Phase 1
0.6911	Remote Similarity	NPD5003	Discontinued
0.691	Remote Similarity	NPD4779	Clinical (unspecified phase)
0.6904	Remote Similarity	NPD6376	Discontinued
0.6902	Remote Similarity	NPD5105	Approved
0.6902	Remote Similarity	NPD5106	Approved
0.6898	Remote Similarity	NPD8110	Clinical (unspecified phase)
0.6893	Remote Similarity	NPD4550	Clinical (unspecified phase)
0.689	Remote Similarity	NPD1253	Approved
0.689	Remote Similarity	NPD1254	Approved
0.689	Remote Similarity	NPD1255	Approved
0.689	Remote Similarity	NPD1256	Approved
0.6889	Remote Similarity	NPD750	Phase 2
0.6888	Remote Similarity	NPD4862	Clinical (unspecified phase)
0.6882	Remote Similarity	NPD5444	Phase 1
0.6878	Remote Similarity	NPD4315	Phase 2
0.6875	Remote Similarity	NPD6261	Phase 3
0.6869	Remote Similarity	NPD5835	Phase 3
0.6869	Remote Similarity	NPD5834	Phase 3
0.6852	Remote Similarity	NPD1251	Discontinued
0.6851	Remote Similarity	NPD6492	Phase 2
0.6842	Remote Similarity	NPD5575	Clinical (unspecified phase)
0.6833	Remote Similarity	NPD3610	Approved
0.6833	Remote Similarity	NPD3609	Approved
0.6825	Remote Similarity	NPD5912	Clinical (unspecified phase)
0.6825	Remote Similarity	NPD5913	Phase 3
0.6823	Remote Similarity	NPD2880	Discontinued
0.6818	Remote Similarity	NPD7947	Clinical (unspecified phase)
0.6816	Remote Similarity	NPD8094	Discontinued
0.6813	Remote Similarity	NPD6044	Discontinued
0.6806	Remote Similarity	NPD4602	Approved
0.6804	Remote Similarity	NPD4600	Approved
0.6804	Remote Similarity	NPD4601	Approved
0.68	Remote Similarity	NPD4671	Clinical (unspecified phase)
0.68	Remote Similarity	NPD4670	Clinical (unspecified phase)
0.68	Remote Similarity	NPD4669	Clinical (unspecified phase)
0.68	Remote Similarity	NPD7470	Discontinued
0.6798	Remote Similarity	NPD7823	Clinical (unspecified phase)
0.6794	Remote Similarity	NPD7780	Approved
0.6794	Remote Similarity	NPD7781	Approved
0.6789	Remote Similarity	NPD3404	Approved
0.6786	Remote Similarity	NPD6176	Phase 1
0.678	Remote Similarity	NPD6771	Discontinued
0.6774	Remote Similarity	NPD7483	Phase 2
0.6774	Remote Similarity	NPD4957	Phase 2
0.6774	Remote Similarity	NPD7482	Phase 2
0.6762	Remote Similarity	NPD7824	Approved
0.6755	Remote Similarity	NPD7394	Phase 2
0.6754	Remote Similarity	NPD4348	Clinical (unspecified phase)
0.6751	Remote Similarity	NPD2721	Clinical (unspecified phase)
0.6747	Remote Similarity	NPD6554	Approved
0.6747	Remote Similarity	NPD45	Approved
0.674	Remote Similarity	NPD6827	Clinical (unspecified phase)
0.674	Remote Similarity	NPD6828	Phase 2
0.6736	Remote Similarity	NPD7948	Phase 1
0.6731	Remote Similarity	NPD7271	Approved
0.6725	Remote Similarity	NPD7469	Discontinued
0.6723	Remote Similarity	NPD6454	Clinical (unspecified phase)
0.6719	Remote Similarity	NPD7944	Discontinued
0.6718	Remote Similarity	NPD4500	Approved
0.6718	Remote Similarity	NPD4501	Approved
0.6716	Remote Similarity	NPD8406	Clinical (unspecified phase)
0.6703	Remote Similarity	NPD5898	Approved
0.6703	Remote Similarity	NPD5899	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