NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	333.02
Volume:	290.134
LogP:	0.67
LogD:	0.522
LogS:	-3.225
# Rotatable Bonds:	6
TPSA:	70.62
# H-Bond Aceptor:	5
# H-Bond Donor:	1
# Rings:	2
# Heavy Atoms:	8

MedChem Properties

QED Drug-Likeness Score:	0.658
Synthetic Accessibility Score:	4.034
Fsp3:	0.417
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.274
MDCK Permeability:	1.1510654076118954e-05
Pgp-inhibitor:	0.011
Pgp-substrate:	0.998
Human Intestinal Absorption (HIA):	0.276
20% Bioavailability (F20%):	0.784
30% Bioavailability (F30%):	0.828

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.873
Plasma Protein Binding (PPB):	45.05666732788086%
Volume Distribution (VD):	1.008
Pgp-substrate:	20.371980667114258%

ADMET: Metabolism

CYP1A2-inhibitor:	0.866
CYP1A2-substrate:	0.812
CYP2C19-inhibitor:	0.826
CYP2C19-substrate:	0.87
CYP2C9-inhibitor:	0.495
CYP2C9-substrate:	0.926
CYP2D6-inhibitor:	0.648
CYP2D6-substrate:	0.722
CYP3A4-inhibitor:	0.041
CYP3A4-substrate:	0.277

ADMET: Excretion

Clearance (CL):	6.555
Half-life (T1/2):	0.379

ADMET: Toxicity

hERG Blockers:	0.018
Human Hepatotoxicity (H-HT):	0.143
Drug-inuced Liver Injury (DILI):	0.911
AMES Toxicity:	0.337
Rat Oral Acute Toxicity:	0.957
Maximum Recommended Daily Dose:	0.177
Skin Sensitization:	0.571
Carcinogencity:	0.403
Eye Corrosion:	0.004
Eye Irritation:	0.028
Respiratory Toxicity:	0.974

Download Data

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

Natural Product: NPC474652

Natural Product ID:	NPC474652
*Common Name:**	Varacin C Acetate
IUPAC Name:	N-[2-(4,5-dimethoxy-1-oxo-1$l^{4},2,3-benzotrithiol-7-yl)ethyl]acetamide
Synonyms:	Varacin C Acetate
Standard InCHIKey:	ANNCBKZGYGXSEH-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C12H15NO4S3/c1-7(14)13-5-4-8-6-9(16-2)10(17-3)11-12(8)20(15)19-18-11/h6H,4-5H2,1-3H3,(H,13,14)
SMILES:	CC(=O)NCCC1=CC(=C(C2=C1S(=O)SS2)OC)OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL478174
PubChem CID:	11724398
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000264] Organic acids and derivatives [CHEMONTID:0000265] Carboxylic acids and derivatives [CHEMONTID:0001093] Carboxylic acid derivatives [CHEMONTID:0000475] Carboxylic acid amides [CHEMONTID:0003922] Acetamides [CHEMONTID:0004252] N-acetyl-2-arylethylamines

*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
NPO32529	polycitor sp.	Species	Polycitoridae	Eukaryota	n.a.	n.a.	n.a.	PMID[7769392]

☑ 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
Others	1

Activity Type	# Activity
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT20	Organism	Candida albicans	Candida albicans	IZ	=	20.0	mm	PMID[454388]

☑ 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 NPC474652 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	265
0.1-0.2	3128
0.2-0.3	13966
0.3-0.4	5428
0.4-0.5	12417
0.5-0.6	6393
0.6-0.7	1022
0.7-0.8	70
0.8-0.85	2
0.85-0.9	2
0.9-0.95	1
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC474649
0.9708	High Similarity	NPC475698
0.9357	High Similarity	NPC474553
0.8611	High Similarity	NPC59661
0.8523	High Similarity	NPC296858
0.8258	Intermediate Similarity	NPC131440
0.805	Intermediate Similarity	NPC94292
0.7961	Intermediate Similarity	NPC69623
0.7829	Intermediate Similarity	NPC261940
0.7727	Intermediate Similarity	NPC226601
0.7711	Intermediate Similarity	NPC177023
0.7697	Intermediate Similarity	NPC130921
0.7655	Intermediate Similarity	NPC301713
0.7603	Intermediate Similarity	NPC153990
0.7517	Intermediate Similarity	NPC214869
0.7453	Intermediate Similarity	NPC191200
0.7453	Intermediate Similarity	NPC291583
0.745	Intermediate Similarity	NPC114102
0.74	Intermediate Similarity	NPC130595
0.74	Intermediate Similarity	NPC93882
0.7391	Intermediate Similarity	NPC28414
0.7391	Intermediate Similarity	NPC298924
0.7383	Intermediate Similarity	NPC195749
0.7383	Intermediate Similarity	NPC52029
0.7383	Intermediate Similarity	NPC35961
0.7365	Intermediate Similarity	NPC157740
0.7365	Intermediate Similarity	NPC99798
0.7365	Intermediate Similarity	NPC191302
0.7351	Intermediate Similarity	NPC313737
0.7351	Intermediate Similarity	NPC6854
0.7351	Intermediate Similarity	NPC285078
0.7324	Intermediate Similarity	NPC120075
0.7315	Intermediate Similarity	NPC246974
0.7315	Intermediate Similarity	NPC155838
0.7315	Intermediate Similarity	NPC147247
0.7303	Intermediate Similarity	NPC218530
0.7297	Intermediate Similarity	NPC156944
0.7297	Intermediate Similarity	NPC251466
0.7279	Intermediate Similarity	NPC300955
0.7273	Intermediate Similarity	NPC257143
0.7248	Intermediate Similarity	NPC41331
0.7248	Intermediate Similarity	NPC251571
0.7248	Intermediate Similarity	NPC291449
0.723	Intermediate Similarity	NPC182147
0.723	Intermediate Similarity	NPC152186
0.723	Intermediate Similarity	NPC207541
0.723	Intermediate Similarity	NPC170583
0.723	Intermediate Similarity	NPC246133
0.723	Intermediate Similarity	NPC71105
0.7219	Intermediate Similarity	NPC255550
0.7219	Intermediate Similarity	NPC308885
0.7211	Intermediate Similarity	NPC140359
0.7211	Intermediate Similarity	NPC13020
0.72	Intermediate Similarity	NPC469977
0.7161	Intermediate Similarity	NPC14600
0.7161	Intermediate Similarity	NPC160607
0.7161	Intermediate Similarity	NPC312770
0.7161	Intermediate Similarity	NPC204848
0.7161	Intermediate Similarity	NPC41473
0.7152	Intermediate Similarity	NPC470706
0.7143	Intermediate Similarity	NPC298486
0.7133	Intermediate Similarity	NPC186898
0.7115	Intermediate Similarity	NPC299583
0.7105	Intermediate Similarity	NPC476570
0.7078	Intermediate Similarity	NPC473463
0.707	Intermediate Similarity	NPC77572
0.7051	Intermediate Similarity	NPC254610
0.7006	Intermediate Similarity	NPC296898
0.6993	Remote Similarity	NPC142599
0.697	Remote Similarity	NPC206372
0.697	Remote Similarity	NPC203424
0.6968	Remote Similarity	NPC282477
0.6968	Remote Similarity	NPC284855
0.6939	Remote Similarity	NPC53596
0.6939	Remote Similarity	NPC289330
0.6939	Remote Similarity	NPC160120
0.6939	Remote Similarity	NPC17388
0.6939	Remote Similarity	NPC471308
0.6933	Remote Similarity	NPC105513
0.6923	Remote Similarity	NPC11147
0.6884	Remote Similarity	NPC292792
0.6883	Remote Similarity	NPC329595
0.6883	Remote Similarity	NPC326599
0.6871	Remote Similarity	NPC115144
0.6871	Remote Similarity	NPC277857
0.6852	Remote Similarity	NPC5462
0.6846	Remote Similarity	NPC211992
0.6839	Remote Similarity	NPC118419
0.6835	Remote Similarity	NPC193528
0.6831	Remote Similarity	NPC137685
0.6818	Remote Similarity	NPC160193
0.6818	Remote Similarity	NPC262641
0.6813	Remote Similarity	NPC275150
0.68	Remote Similarity	NPC471314
0.68	Remote Similarity	NPC471315
0.6797	Remote Similarity	NPC291847
0.6797	Remote Similarity	NPC172403
0.6788	Remote Similarity	NPC182119
0.6783	Remote Similarity	NPC156840
0.6783	Remote Similarity	NPC257124
0.6783	Remote Similarity	NPC8547
0.6783	Remote Similarity	NPC173746
0.6783	Remote Similarity	NPC166837
0.6779	Remote Similarity	NPC183262
0.6772	Remote Similarity	NPC416184
0.6772	Remote Similarity	NPC131204
0.6772	Remote Similarity	NPC7018
0.6772	Remote Similarity	NPC301050
0.677	Remote Similarity	NPC222039
0.677	Remote Similarity	NPC100478
0.6757	Remote Similarity	NPC43275
0.6747	Remote Similarity	NPC478189
0.6739	Remote Similarity	NPC310905
0.6739	Remote Similarity	NPC12714
0.6738	Remote Similarity	NPC227894
0.6727	Remote Similarity	NPC470935
0.6727	Remote Similarity	NPC471032
0.6713	Remote Similarity	NPC31279
0.6711	Remote Similarity	NPC263835
0.6688	Remote Similarity	NPC160692
0.6667	Remote Similarity	NPC231884
0.6667	Remote Similarity	NPC167944
0.6667	Remote Similarity	NPC275027
0.6667	Remote Similarity	NPC42793
0.6646	Remote Similarity	NPC327623
0.6645	Remote Similarity	NPC211218
0.6644	Remote Similarity	NPC268572
0.6643	Remote Similarity	NPC7097
0.6643	Remote Similarity	NPC233731
0.6643	Remote Similarity	NPC246358
0.6643	Remote Similarity	NPC36108
0.6643	Remote Similarity	NPC127326
0.6627	Remote Similarity	NPC153644
0.6622	Remote Similarity	NPC293619
0.6607	Remote Similarity	NPC127402
0.6607	Remote Similarity	NPC52475
0.6605	Remote Similarity	NPC66518
0.6604	Remote Similarity	NPC475828
0.6601	Remote Similarity	NPC62101
0.6601	Remote Similarity	NPC95733
0.6577	Remote Similarity	NPC474040
0.6577	Remote Similarity	NPC122009
0.6577	Remote Similarity	NPC63083
0.6577	Remote Similarity	NPC205502
0.6577	Remote Similarity	NPC474214
0.6577	Remote Similarity	NPC255675
0.6577	Remote Similarity	NPC470626
0.6575	Remote Similarity	NPC165106
0.6573	Remote Similarity	NPC146530
0.6568	Remote Similarity	NPC18614
0.6554	Remote Similarity	NPC221049
0.6552	Remote Similarity	NPC139617
0.6552	Remote Similarity	NPC21890
0.6552	Remote Similarity	NPC55300
0.6552	Remote Similarity	NPC195873
0.6552	Remote Similarity	NPC78918
0.6543	Remote Similarity	NPC477838
0.6543	Remote Similarity	NPC477837
0.6536	Remote Similarity	NPC31344
0.6536	Remote Similarity	NPC317769
0.6533	Remote Similarity	NPC474320
0.6533	Remote Similarity	NPC24474
0.6533	Remote Similarity	NPC135961
0.6533	Remote Similarity	NPC311595
0.6533	Remote Similarity	NPC181969
0.6533	Remote Similarity	NPC320987
0.6531	Remote Similarity	NPC294941
0.6529	Remote Similarity	NPC226941
0.6529	Remote Similarity	NPC14005
0.6529	Remote Similarity	NPC108957
0.6522	Remote Similarity	NPC253429
0.651	Remote Similarity	NPC164386
0.651	Remote Similarity	NPC283468
0.6509	Remote Similarity	NPC474560
0.6507	Remote Similarity	NPC165646
0.6503	Remote Similarity	NPC323204
0.6503	Remote Similarity	NPC258171
0.6503	Remote Similarity	NPC213206
0.6503	Remote Similarity	NPC328750
0.6503	Remote Similarity	NPC188163
0.6503	Remote Similarity	NPC474915
0.65	Remote Similarity	NPC264956
0.6491	Remote Similarity	NPC107602
0.649	Remote Similarity	NPC321133
0.649	Remote Similarity	NPC95614
0.649	Remote Similarity	NPC35071
0.649	Remote Similarity	NPC177475
0.649	Remote Similarity	NPC56214
0.649	Remote Similarity	NPC242885
0.649	Remote Similarity	NPC148615
0.649	Remote Similarity	NPC232316
0.649	Remote Similarity	NPC344161
0.649	Remote Similarity	NPC165133
0.649	Remote Similarity	NPC227217
0.649	Remote Similarity	NPC117780
0.6486	Remote Similarity	NPC303370
0.6486	Remote Similarity	NPC473264
0.6486	Remote Similarity	NPC47194
0.6486	Remote Similarity	NPC475815
0.6485	Remote Similarity	NPC294249

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 NPC474652 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	164
0.1-0.2	1002
0.2-0.3	1460
0.3-0.4	2848
0.4-0.5	2429
0.5-0.6	1062
0.6-0.7	176
0.7-0.8	9
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.74	Intermediate Similarity	NPD2674	Phase 3
0.7349	Intermediate Similarity	NPD2644	Approved
0.7337	Intermediate Similarity	NPD730	Discontinued
0.7226	Intermediate Similarity	NPD2161	Phase 2
0.7219	Intermediate Similarity	NPD3144	Approved
0.7219	Intermediate Similarity	NPD3145	Approved
0.7188	Intermediate Similarity	NPD4739	Approved
0.7073	Intermediate Similarity	NPD1642	Discontinued
0.707	Intermediate Similarity	NPD1375	Discontinued
0.7048	Intermediate Similarity	NPD487	Discontinued
0.7044	Intermediate Similarity	NPD6331	Phase 2
0.7025	Intermediate Similarity	NPD7153	Discontinued
0.698	Remote Similarity	NPD1669	Approved
0.697	Remote Similarity	NPD4179	Approved
0.697	Remote Similarity	NPD4180	Approved
0.6948	Remote Similarity	NPD554	Clinical (unspecified phase)
0.6928	Remote Similarity	NPD2669	Clinical (unspecified phase)
0.6897	Remote Similarity	NPD5708	Clinical (unspecified phase)
0.6867	Remote Similarity	NPD3676	Clinical (unspecified phase)
0.6863	Remote Similarity	NPD5752	Clinical (unspecified phase)
0.6832	Remote Similarity	NPD6658	Clinical (unspecified phase)
0.681	Remote Similarity	NPD1787	Approved
0.681	Remote Similarity	NPD1786	Approved
0.681	Remote Similarity	NPD1785	Approved
0.6807	Remote Similarity	NPD6055	Clinical (unspecified phase)
0.6805	Remote Similarity	NPD6374	Clinical (unspecified phase)
0.6783	Remote Similarity	NPD228	Approved
0.6774	Remote Similarity	NPD5718	Phase 2
0.6765	Remote Similarity	NPD3075	Approved
0.6746	Remote Similarity	NPD5772	Approved
0.6746	Remote Similarity	NPD5773	Approved
0.6731	Remote Similarity	NPD1726	Clinical (unspecified phase)
0.6727	Remote Similarity	NPD7526	Approved
0.6727	Remote Similarity	NPD7527	Clinical (unspecified phase)
0.6727	Remote Similarity	NPD52	Approved
0.6711	Remote Similarity	NPD2922	Phase 1
0.6688	Remote Similarity	NPD1712	Approved
0.6667	Remote Similarity	NPD1771	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD4123	Phase 3
0.6667	Remote Similarity	NPD4236	Phase 3
0.6667	Remote Similarity	NPD3060	Approved
0.6667	Remote Similarity	NPD6896	Approved
0.6667	Remote Similarity	NPD4237	Approved
0.6667	Remote Similarity	NPD4162	Approved
0.6667	Remote Similarity	NPD6895	Approved
0.6647	Remote Similarity	NPD5563	Clinical (unspecified phase)
0.6646	Remote Similarity	NPD1803	Phase 3
0.6624	Remote Similarity	NPD839	Approved
0.6624	Remote Similarity	NPD840	Approved
0.6607	Remote Similarity	NPD4005	Discontinued
0.6604	Remote Similarity	NPD2653	Approved
0.6604	Remote Similarity	NPD2157	Approved
0.6575	Remote Similarity	NPD5283	Phase 1
0.6529	Remote Similarity	NPD5089	Approved
0.6529	Remote Similarity	NPD5090	Approved
0.6527	Remote Similarity	NPD5261	Clinical (unspecified phase)
0.6503	Remote Similarity	NPD4664	Clinical (unspecified phase)
0.6497	Remote Similarity	NPD1024	Discontinued
0.649	Remote Similarity	NPD2667	Approved
0.649	Remote Similarity	NPD2668	Approved
0.6485	Remote Similarity	NPD5241	Discontinued
0.6474	Remote Similarity	NPD3674	Clinical (unspecified phase)
0.6471	Remote Similarity	NPD4675	Approved
0.6471	Remote Similarity	NPD1244	Clinical (unspecified phase)
0.6471	Remote Similarity	NPD4678	Approved
0.6456	Remote Similarity	NPD5109	Approved
0.6456	Remote Similarity	NPD5111	Phase 2
0.6456	Remote Similarity	NPD5110	Phase 2
0.6453	Remote Similarity	NPD1006	Clinical (unspecified phase)
0.6437	Remote Similarity	NPD7975	Clinical (unspecified phase)
0.6437	Remote Similarity	NPD4055	Discovery
0.6424	Remote Similarity	NPD1357	Approved
0.642	Remote Similarity	NPD6029	Clinical (unspecified phase)
0.642	Remote Similarity	NPD6028	Clinical (unspecified phase)
0.6419	Remote Similarity	NPD9299	Approved
0.641	Remote Similarity	NPD558	Phase 2
0.6405	Remote Similarity	NPD3705	Approved
0.6405	Remote Similarity	NPD776	Approved
0.6402	Remote Similarity	NPD2030	Discontinued
0.6402	Remote Similarity	NPD1044	Clinical (unspecified phase)
0.6395	Remote Similarity	NPD9379	Approved
0.6395	Remote Similarity	NPD7945	Clinical (unspecified phase)
0.6395	Remote Similarity	NPD9377	Approved
0.6395	Remote Similarity	NPD821	Approved
0.6386	Remote Similarity	NPD5084	Clinical (unspecified phase)
0.6386	Remote Similarity	NPD2219	Phase 1
0.6358	Remote Similarity	NPD2977	Approved
0.6358	Remote Similarity	NPD6111	Discontinued
0.6358	Remote Similarity	NPD6064	Phase 1
0.6358	Remote Similarity	NPD2978	Approved
0.6353	Remote Similarity	NPD3686	Approved
0.6353	Remote Similarity	NPD3687	Approved
0.6353	Remote Similarity	NPD4210	Discontinued
0.6347	Remote Similarity	NPD6783	Clinical (unspecified phase)
0.6347	Remote Similarity	NPD7124	Phase 2
0.6343	Remote Similarity	NPD5604	Discontinued
0.6331	Remote Similarity	NPD2236	Approved
0.6319	Remote Similarity	NPD4108	Discontinued
0.6303	Remote Similarity	NPD1372	Clinical (unspecified phase)
0.6296	Remote Similarity	NPD2492	Phase 1
0.6296	Remote Similarity	NPD1772	Clinical (unspecified phase)
0.6273	Remote Similarity	NPD1558	Phase 1
0.6272	Remote Similarity	NPD4584	Approved
0.6271	Remote Similarity	NPD7201	Clinical (unspecified phase)
0.6267	Remote Similarity	NPD709	Approved
0.6265	Remote Similarity	NPD5177	Phase 3
0.6258	Remote Similarity	NPD2230	Approved
0.6258	Remote Similarity	NPD2233	Approved
0.6258	Remote Similarity	NPD2232	Approved
0.6257	Remote Similarity	NPD4083	Discontinued
0.625	Remote Similarity	NPD1039	Discontinued
0.6243	Remote Similarity	NPD7438	Suspended
0.6242	Remote Similarity	NPD3656	Approved
0.6242	Remote Similarity	NPD5085	Clinical (unspecified phase)
0.6236	Remote Similarity	NPD7802	Discontinued
0.6235	Remote Similarity	NPD6390	Discontinued
0.6229	Remote Similarity	NPD2560	Approved
0.6229	Remote Similarity	NPD2563	Approved
0.622	Remote Similarity	NPD3693	Clinical (unspecified phase)
0.6218	Remote Similarity	NPD3685	Discontinued
0.6213	Remote Similarity	NPD4357	Discontinued
0.6211	Remote Similarity	NPD3058	Clinical (unspecified phase)
0.6207	Remote Similarity	NPD5720	Discontinued
0.6205	Remote Similarity	NPD3655	Clinical (unspecified phase)
0.6199	Remote Similarity	NPD6030	Approved
0.6199	Remote Similarity	NPD6031	Approved
0.6199	Remote Similarity	NPD6662	Clinical (unspecified phase)
0.6199	Remote Similarity	NPD2122	Discontinued
0.619	Remote Similarity	NPD5307	Clinical (unspecified phase)
0.6184	Remote Similarity	NPD5536	Phase 2
0.6178	Remote Similarity	NPD9634	Clinical (unspecified phase)
0.6176	Remote Similarity	NPD1754	Clinical (unspecified phase)
0.6169	Remote Similarity	NPD9381	Approved
0.6169	Remote Similarity	NPD9384	Approved
0.6164	Remote Similarity	NPD2040	Clinical (unspecified phase)
0.6149	Remote Similarity	NPD1757	Discontinued
0.6149	Remote Similarity	NPD4773	Phase 2
0.6149	Remote Similarity	NPD4772	Phase 2
0.6145	Remote Similarity	NPD3540	Phase 1
0.614	Remote Similarity	NPD1350	Approved
0.614	Remote Similarity	NPD1349	Approved
0.614	Remote Similarity	NPD1351	Approved
0.614	Remote Similarity	NPD3647	Clinical (unspecified phase)
0.6135	Remote Similarity	NPD3657	Discovery
0.6127	Remote Similarity	NPD3866	Clinical (unspecified phase)
0.6127	Remote Similarity	NPD746	Clinical (unspecified phase)
0.6127	Remote Similarity	NPD3111	Phase 1
0.6125	Remote Similarity	NPD600	Approved
0.6125	Remote Similarity	NPD596	Approved
0.6122	Remote Similarity	NPD2684	Approved
0.6115	Remote Similarity	NPD9622	Approved
0.6115	Remote Similarity	NPD4379	Clinical (unspecified phase)
0.6111	Remote Similarity	NPD1423	Approved
0.6111	Remote Similarity	NPD7477	Discontinued
0.6105	Remote Similarity	NPD3639	Approved
0.6105	Remote Similarity	NPD3640	Phase 3
0.6105	Remote Similarity	NPD3641	Approved
0.6101	Remote Similarity	NPD9621	Approved
0.6101	Remote Similarity	NPD7905	Discontinued
0.6101	Remote Similarity	NPD6584	Phase 3
0.6101	Remote Similarity	NPD9620	Approved
0.6101	Remote Similarity	NPD9619	Approved
0.6099	Remote Similarity	NPD5602	Clinical (unspecified phase)
0.6093	Remote Similarity	NPD595	Approved
0.6093	Remote Similarity	NPD593	Approved
0.6093	Remote Similarity	NPD475	Phase 2
0.6092	Remote Similarity	NPD6875	Approved
0.6092	Remote Similarity	NPD6876	Approved
0.6087	Remote Similarity	NPD3027	Phase 3
0.6084	Remote Similarity	NPD3539	Phase 1
0.6082	Remote Similarity	NPD1424	Approved
0.608	Remote Similarity	NPD6818	Clinical (unspecified phase)
0.6074	Remote Similarity	NPD2238	Phase 2
0.6074	Remote Similarity	NPD5837	Clinical (unspecified phase)
0.6067	Remote Similarity	NPD7833	Phase 2
0.6067	Remote Similarity	NPD7832	Clinical (unspecified phase)
0.6067	Remote Similarity	NPD7831	Phase 2
0.6067	Remote Similarity	NPD7843	Approved
0.6057	Remote Similarity	NPD3796	Clinical (unspecified phase)
0.6057	Remote Similarity	NPD7110	Phase 1
0.6057	Remote Similarity	NPD7109	Clinical (unspecified phase)
0.6054	Remote Similarity	NPD2759	Clinical (unspecified phase)
0.6053	Remote Similarity	NPD7157	Approved
0.6051	Remote Similarity	NPD2337	Clinical (unspecified phase)
0.6051	Remote Similarity	NPD2231	Phase 2
0.6051	Remote Similarity	NPD2235	Phase 2
0.6039	Remote Similarity	NPD1182	Approved
0.6038	Remote Similarity	NPD1819	Approved
0.6038	Remote Similarity	NPD3055	Approved
0.6038	Remote Similarity	NPD1817	Approved
0.6038	Remote Similarity	NPD1818	Approved
0.6038	Remote Similarity	NPD3053	Approved
0.6038	Remote Similarity	NPD1820	Approved
0.6036	Remote Similarity	NPD4110	Phase 3
0.6036	Remote Similarity	NPD4109	Clinical (unspecified phase)
0.6034	Remote Similarity	NPD4017	Approved
0.6034	Remote Similarity	NPD824	Approved
0.6031	Remote Similarity	NPD7034	Discontinued
0.6025	Remote Similarity	NPD682	Discontinued
0.6024	Remote Similarity	NPD3152	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