NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	349.03
Volume:	310.995
LogP:	2.696
LogD:	2.948
LogS:	-5.033
# Rotatable Bonds:	6
TPSA:	21.7
# H-Bond Aceptor:	3
# H-Bond Donor:	0
# Rings:	2
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.557
Synthetic Accessibility Score:	3.612
Fsp3:	0.538
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:	-4.9
MDCK Permeability:	2.297192986588925e-05
Pgp-inhibitor:	0.016
Pgp-substrate:	0.913
Human Intestinal Absorption (HIA):	0.023
20% Bioavailability (F20%):	0.002
30% Bioavailability (F30%):	0.001

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.725
Plasma Protein Binding (PPB):	73.751220703125%
Volume Distribution (VD):	1.935
Pgp-substrate:	10.765872955322266%

ADMET: Metabolism

CYP1A2-inhibitor:	0.927
CYP1A2-substrate:	0.968
CYP2C19-inhibitor:	0.984
CYP2C19-substrate:	0.969
CYP2C9-inhibitor:	0.486
CYP2C9-substrate:	0.914
CYP2D6-inhibitor:	0.2
CYP2D6-substrate:	0.907
CYP3A4-inhibitor:	0.047
CYP3A4-substrate:	0.887

ADMET: Excretion

Clearance (CL):	10.659
Half-life (T1/2):	0.105

ADMET: Toxicity

hERG Blockers:	0.118
Human Hepatotoxicity (H-HT):	0.394
Drug-inuced Liver Injury (DILI):	0.92
AMES Toxicity:	0.491
Rat Oral Acute Toxicity:	0.978
Maximum Recommended Daily Dose:	0.098
Skin Sensitization:	0.891
Carcinogencity:	0.072
Eye Corrosion:	0.266
Eye Irritation:	0.064
Respiratory Toxicity:	0.985

Download Data

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

Natural Product: NPC69623

Natural Product ID:	NPC69623
*Common Name:**	3,4-Dimethoxy-6-(2'-N,N-Dimethylaminoethyl)-5-(Methylthio)Benzotrithiane
IUPAC Name:	2-(4,5-dimethoxy-6-methylsulfanyl-1,2,3-benzotrithiol-7-yl)-N,N-dimethylethanamine
Synonyms:
Standard InCHIKey:	VDPRVSQPQCVGDF-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C13H19NO2S4/c1-14(2)7-6-8-11(17-5)9(15-3)10(16-4)13-12(8)18-20-19-13/h6-7H2,1-5H3
SMILES:	CSc1c(CCN(C)C)c2SSSc2c(c1OC)OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL222469
PubChem CID:	9997973
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0002279] Benzene and substituted derivatives [CHEMONTID:0000186] Phenethylamines

*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
NPO32940	lissoclinum cf. badium	Species	Didemnidae	Eukaryota	n.a.	Indonesian	n.a.	PMID[17269824]
NPO32940	lissoclinum cf. badium	Species	Didemnidae	Eukaryota	n.a.	n.a.	n.a.	PMID[18977148]
NPO32940	lissoclinum cf. badium	Species	Didemnidae	Eukaryota	n.a.	n.a.	n.a.	PMID[28181805]
NPO17937	[hypocrea] muroiana	Species	Hypocreaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5938	Veronica filiformis	Species	Plantaginaceae	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
EC50	1
IC50	3
Others	11

Activity Type	# Activity
Cell Line	1
NON-MOLECULAR	1
Organism	11
Others	1
Protein Family	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT3171	Cell Line	V79	Cricetulus griseus	IC50	=	190.0	nM	PMID[546202]
NPT3481	Organism	Mucor hiemalis	Mucor hiemalis	IZ	=	23.0	mm	PMID[546201]
NPT3481	Organism	Mucor hiemalis	Mucor hiemalis	IZ	=	17.4	mm	PMID[546201]
NPT312	Organism	Saccharomyces cerevisiae	Saccharomyces cerevisiae	IZ	=	11.8	mm	PMID[546201]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	IZ	=	10.3	mm	PMID[546201]
NPT19	Organism	Escherichia coli	Escherichia coli	IZ	=	17.8	mm	PMID[546201]
NPT19	Organism	Escherichia coli	Escherichia coli	IZ	=	14.4	mm	PMID[546201]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	EC50	=	190.0	nM	PMID[546201]
NPT316	Protein Family	Protein kinase C (PKC)	Homo sapiens	IC50	=	0.3	ug.mL-1	PMID[546202]
NPT2	Others	Unspecified		IC50	>	25.0	ug.mL-1	PMID[546202]
NPT3481	Organism	Mucor hiemalis	Mucor hiemalis	IZ	=	10.3	mm	PMID[546202]
NPT26456	ORGANISM	Ruegeria atlantica	Ruegeria atlantica	IZ	=	10.3	mm	PMID[546202]
NPT312	Organism	Saccharomyces cerevisiae	Saccharomyces cerevisiae	IZ	=	10.3	mm	PMID[546202]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	IZ	=	10.3	mm	PMID[546202]
NPT19	Organism	Escherichia coli	Escherichia coli	IZ	=	10.3	mm	PMID[546202]

☑ 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 NPC69623 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	352
0.1-0.2	4648
0.2-0.3	14711
0.3-0.4	9015
0.4-0.5	11505
0.5-0.6	2316
0.6-0.7	130
0.7-0.8	5
0.8-0.85	6
0.85-0.9	5
0.9-0.95	2
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.971	High Similarity	NPC226601
0.9178	High Similarity	NPC191200
0.9178	High Similarity	NPC291583
0.911	High Similarity	NPC298924
0.911	High Similarity	NPC28414
0.8933	High Similarity	NPC257143
0.8621	High Similarity	NPC261940
0.8428	Intermediate Similarity	NPC177023
0.8302	Intermediate Similarity	NPC130921
0.8212	Intermediate Similarity	NPC296858
0.8176	Intermediate Similarity	NPC475698
0.8101	Intermediate Similarity	NPC94292
0.8041	Intermediate Similarity	NPC59661
0.8	Intermediate Similarity	NPC474553
0.7962	Intermediate Similarity	NPC131440
0.7961	Intermediate Similarity	NPC474652
0.7961	Intermediate Similarity	NPC474649
0.6959	Remote Similarity	NPC298486
0.6802	Remote Similarity	NPC206941
0.6753	Remote Similarity	NPC160193
0.6752	Remote Similarity	NPC11147
0.6732	Remote Similarity	NPC172403
0.6667	Remote Similarity	NPC118419
0.6667	Remote Similarity	NPC120075
0.6645	Remote Similarity	NPC262641
0.6604	Remote Similarity	NPC7018
0.6604	Remote Similarity	NPC416184
0.6603	Remote Similarity	NPC476570
0.65	Remote Similarity	NPC231884
0.65	Remote Similarity	NPC42793
0.65	Remote Similarity	NPC167944
0.648	Remote Similarity	NPC20395
0.646	Remote Similarity	NPC193528
0.6452	Remote Similarity	NPC301713
0.6429	Remote Similarity	NPC105513
0.6415	Remote Similarity	NPC160692
0.641	Remote Similarity	NPC153990
0.6398	Remote Similarity	NPC131204
0.6398	Remote Similarity	NPC301050
0.6386	Remote Similarity	NPC145304
0.638	Remote Similarity	NPC314682
0.6364	Remote Similarity	NPC140359
0.6364	Remote Similarity	NPC13020
0.6358	Remote Similarity	NPC253429
0.6341	Remote Similarity	NPC188163
0.6341	Remote Similarity	NPC474915
0.6341	Remote Similarity	NPC328750
0.6341	Remote Similarity	NPC213206
0.634	Remote Similarity	NPC211992
0.6335	Remote Similarity	NPC475828
0.6316	Remote Similarity	NPC203424
0.6316	Remote Similarity	NPC206372
0.6306	Remote Similarity	NPC291847
0.6287	Remote Similarity	NPC110337
0.6287	Remote Similarity	NPC130926
0.6272	Remote Similarity	NPC130941
0.6272	Remote Similarity	NPC475959
0.6265	Remote Similarity	NPC128019
0.6265	Remote Similarity	NPC476567
0.6265	Remote Similarity	NPC136860
0.6258	Remote Similarity	NPC252107
0.625	Remote Similarity	NPC214869
0.625	Remote Similarity	NPC130595
0.625	Remote Similarity	NPC93882
0.6242	Remote Similarity	NPC323204
0.6235	Remote Similarity	NPC219162
0.6235	Remote Similarity	NPC211296
0.6224	Remote Similarity	NPC292792
0.622	Remote Similarity	NPC210086
0.6211	Remote Similarity	NPC6854
0.6211	Remote Similarity	NPC313737
0.6211	Remote Similarity	NPC285078
0.6203	Remote Similarity	NPC191302
0.6203	Remote Similarity	NPC99798
0.6203	Remote Similarity	NPC157740
0.6196	Remote Similarity	NPC145446
0.6196	Remote Similarity	NPC137172
0.6196	Remote Similarity	NPC99078
0.619	Remote Similarity	NPC185838
0.6188	Remote Similarity	NPC114102
0.6176	Remote Similarity	NPC59907
0.6176	Remote Similarity	NPC37144
0.6173	Remote Similarity	NPC218530
0.6173	Remote Similarity	NPC167096
0.6164	Remote Similarity	NPC155838
0.6164	Remote Similarity	NPC147247
0.6164	Remote Similarity	NPC246974
0.6159	Remote Similarity	NPC220923
0.6159	Remote Similarity	NPC28641
0.6159	Remote Similarity	NPC248505
0.6159	Remote Similarity	NPC194359
0.6159	Remote Similarity	NPC470707
0.6159	Remote Similarity	NPC95366
0.6159	Remote Similarity	NPC225745
0.6154	Remote Similarity	NPC473934
0.6149	Remote Similarity	NPC318862
0.614	Remote Similarity	NPC470088
0.6139	Remote Similarity	NPC251466
0.6139	Remote Similarity	NPC156944
0.6135	Remote Similarity	NPC205178
0.6135	Remote Similarity	NPC180647
0.6135	Remote Similarity	NPC255817
0.6135	Remote Similarity	NPC196609
0.6135	Remote Similarity	NPC96406
0.6135	Remote Similarity	NPC73883
0.6135	Remote Similarity	NPC277042
0.6135	Remote Similarity	NPC230698
0.6135	Remote Similarity	NPC251454
0.6135	Remote Similarity	NPC136330
0.6127	Remote Similarity	NPC148898
0.6127	Remote Similarity	NPC210148
0.6127	Remote Similarity	NPC233029
0.6125	Remote Similarity	NPC195749
0.6125	Remote Similarity	NPC52029
0.6125	Remote Similarity	NPC35961
0.6121	Remote Similarity	NPC231572
0.6118	Remote Similarity	NPC95075
0.6118	Remote Similarity	NPC179825
0.6118	Remote Similarity	NPC321505
0.6118	Remote Similarity	NPC51957
0.6118	Remote Similarity	NPC253883
0.6118	Remote Similarity	NPC476144
0.6118	Remote Similarity	NPC191376
0.6118	Remote Similarity	NPC210437
0.6118	Remote Similarity	NPC90844
0.6118	Remote Similarity	NPC16107
0.6118	Remote Similarity	NPC106295
0.6118	Remote Similarity	NPC476151
0.6115	Remote Similarity	NPC300955
0.6105	Remote Similarity	NPC274026
0.6105	Remote Similarity	NPC13397
0.6104	Remote Similarity	NPC321133
0.6101	Remote Similarity	NPC41331
0.6101	Remote Similarity	NPC291449
0.6087	Remote Similarity	NPC308885
0.6087	Remote Similarity	NPC329595
0.6087	Remote Similarity	NPC255550
0.6087	Remote Similarity	NPC326599
0.6084	Remote Similarity	NPC310905
0.6084	Remote Similarity	NPC12714
0.6082	Remote Similarity	NPC246587
0.6082	Remote Similarity	NPC24233
0.6082	Remote Similarity	NPC135538
0.6082	Remote Similarity	NPC7467
0.6082	Remote Similarity	NPC147390
0.6082	Remote Similarity	NPC476571
0.6082	Remote Similarity	NPC428
0.6081	Remote Similarity	NPC137685
0.6081	Remote Similarity	NPC31279
0.6076	Remote Similarity	NPC182147
0.6076	Remote Similarity	NPC71105
0.6076	Remote Similarity	NPC207541
0.6076	Remote Similarity	NPC170583
0.6076	Remote Similarity	NPC246133
0.6076	Remote Similarity	NPC152186
0.6074	Remote Similarity	NPC103947
0.6074	Remote Similarity	NPC94280
0.6074	Remote Similarity	NPC328419
0.6074	Remote Similarity	NPC45783
0.6074	Remote Similarity	NPC193673
0.6074	Remote Similarity	NPC159150
0.6062	Remote Similarity	NPC469977
0.6057	Remote Similarity	NPC93593
0.6057	Remote Similarity	NPC78733
0.6057	Remote Similarity	NPC216459
0.6057	Remote Similarity	NPC41178
0.6057	Remote Similarity	NPC244112
0.6057	Remote Similarity	NPC138487
0.6049	Remote Similarity	NPC217574
0.6047	Remote Similarity	NPC92541
0.6047	Remote Similarity	NPC477565
0.6047	Remote Similarity	NPC103379
0.6036	Remote Similarity	NPC294249
0.6034	Remote Similarity	NPC82285
0.6034	Remote Similarity	NPC133011
0.6025	Remote Similarity	NPC470706
0.6023	Remote Similarity	NPC186063
0.6023	Remote Similarity	NPC323443
0.6023	Remote Similarity	NPC147091
0.6023	Remote Similarity	NPC180756
0.6023	Remote Similarity	NPC146288
0.6014	Remote Similarity	NPC127326
0.6012	Remote Similarity	NPC88249
0.6012	Remote Similarity	NPC138438
0.6012	Remote Similarity	NPC97221
0.6012	Remote Similarity	NPC223125
0.6012	Remote Similarity	NPC908
0.6012	Remote Similarity	NPC151895
0.6012	Remote Similarity	NPC220858
0.6012	Remote Similarity	NPC192768
0.6	Remote Similarity	NPC292003
0.6	Remote Similarity	NPC469978
0.6	Remote Similarity	NPC251571
0.5989	Remote Similarity	NPC148014
0.5989	Remote Similarity	NPC65490
0.5989	Remote Similarity	NPC40389
0.5989	Remote Similarity	NPC129603
0.5989	Remote Similarity	NPC315707
0.5989	Remote Similarity	NPC78359
0.5988	Remote Similarity	NPC77572

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 NPC69623 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	212
0.1-0.2	1195
0.2-0.3	2118
0.3-0.4	3296
0.4-0.5	1735
0.5-0.6	554
0.6-0.7	40
0.7-0.8	0
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
0.6863	Remote Similarity	NPD2669	Clinical (unspecified phase)
0.6839	Remote Similarity	NPD5708	Clinical (unspecified phase)
0.6797	Remote Similarity	NPD5752	Clinical (unspecified phase)
0.671	Remote Similarity	NPD5718	Phase 2
0.6667	Remote Similarity	NPD554	Clinical (unspecified phase)
0.6591	Remote Similarity	NPD730	Discontinued
0.6588	Remote Similarity	NPD487	Discontinued
0.6568	Remote Similarity	NPD1757	Discontinued
0.6509	Remote Similarity	NPD1642	Discontinued
0.65	Remote Similarity	NPD6895	Approved
0.65	Remote Similarity	NPD6896	Approved
0.6481	Remote Similarity	NPD5085	Clinical (unspecified phase)
0.6457	Remote Similarity	NPD7802	Discontinued
0.645	Remote Similarity	NPD6055	Clinical (unspecified phase)
0.6407	Remote Similarity	NPD4739	Approved
0.6369	Remote Similarity	NPD2236	Approved
0.6358	Remote Similarity	NPD6029	Clinical (unspecified phase)
0.6358	Remote Similarity	NPD6028	Clinical (unspecified phase)
0.6341	Remote Similarity	NPD4664	Clinical (unspecified phase)
0.6335	Remote Similarity	NPD2653	Approved
0.6325	Remote Similarity	NPD5084	Clinical (unspecified phase)
0.6316	Remote Similarity	NPD4179	Approved
0.6316	Remote Similarity	NPD4180	Approved
0.6307	Remote Similarity	NPD2644	Approved
0.6287	Remote Similarity	NPD6783	Clinical (unspecified phase)
0.6272	Remote Similarity	NPD6890	Discontinued
0.6264	Remote Similarity	NPD6374	Clinical (unspecified phase)
0.625	Remote Similarity	NPD2674	Phase 3
0.6228	Remote Similarity	NPD5241	Discontinued
0.6205	Remote Similarity	NPD4236	Phase 3
0.6205	Remote Similarity	NPD4162	Approved
0.6205	Remote Similarity	NPD3060	Approved
0.6205	Remote Similarity	NPD4237	Approved
0.6199	Remote Similarity	NPD4210	Discontinued
0.6196	Remote Similarity	NPD6111	Discontinued
0.619	Remote Similarity	NPD7124	Phase 2
0.6135	Remote Similarity	NPD2492	Phase 1
0.6121	Remote Similarity	NPD2161	Phase 2
0.6118	Remote Similarity	NPD4584	Approved
0.6118	Remote Similarity	NPD1771	Clinical (unspecified phase)
0.6104	Remote Similarity	NPD2667	Approved
0.6104	Remote Similarity	NPD2668	Approved
0.6087	Remote Similarity	NPD3144	Approved
0.6087	Remote Similarity	NPD3145	Approved
0.6084	Remote Similarity	NPD1375	Discontinued
0.6069	Remote Similarity	NPD6813	Clinical (unspecified phase)
0.6069	Remote Similarity	NPD746	Clinical (unspecified phase)
0.6048	Remote Similarity	NPD1372	Clinical (unspecified phase)
0.6047	Remote Similarity	NPD3641	Approved
0.6047	Remote Similarity	NPD6662	Clinical (unspecified phase)
0.6047	Remote Similarity	NPD3640	Phase 3
0.6047	Remote Similarity	NPD3639	Approved
0.6038	Remote Similarity	NPD7905	Discontinued
0.6032	Remote Similarity	NPD5188	Clinical (unspecified phase)
0.6023	Remote Similarity	NPD1424	Approved
0.6023	Remote Similarity	NPD1006	Clinical (unspecified phase)
0.6011	Remote Similarity	NPD5087	Clinical (unspecified phase)
0.6	Remote Similarity	NPD6066	Clinical (unspecified phase)
0.5989	Remote Similarity	NPD2563	Approved
0.5989	Remote Similarity	NPD2560	Approved
0.5988	Remote Similarity	NPD1803	Phase 3
0.5987	Remote Similarity	NPD1244	Clinical (unspecified phase)
0.5977	Remote Similarity	NPD4017	Approved
0.5976	Remote Similarity	NPD6331	Phase 2
0.596	Remote Similarity	NPD5283	Phase 1
0.5955	Remote Similarity	NPD3075	Approved
0.5954	Remote Similarity	NPD6030	Approved
0.5954	Remote Similarity	NPD6031	Approved
0.5954	Remote Similarity	NPD2900	Approved
0.5954	Remote Similarity	NPD2901	Approved
0.5952	Remote Similarity	NPD7153	Discontinued
0.5952	Remote Similarity	NPD1044	Clinical (unspecified phase)
0.5943	Remote Similarity	NPD6876	Approved
0.5943	Remote Similarity	NPD6875	Approved
0.5941	Remote Similarity	NPD5307	Clinical (unspecified phase)
0.5933	Remote Similarity	NPD228	Approved
0.5932	Remote Similarity	NPD5563	Clinical (unspecified phase)
0.5932	Remote Similarity	NPD5772	Approved
0.5932	Remote Similarity	NPD2978	Approved
0.5932	Remote Similarity	NPD2977	Approved
0.5932	Remote Similarity	NPD5773	Approved
0.593	Remote Similarity	NPD1754	Clinical (unspecified phase)
0.592	Remote Similarity	NPD3686	Approved
0.592	Remote Similarity	NPD3687	Approved
0.5917	Remote Similarity	NPD5177	Phase 3
0.5909	Remote Similarity	NPD4773	Phase 2
0.5909	Remote Similarity	NPD4772	Phase 2
0.5909	Remote Similarity	NPD7109	Clinical (unspecified phase)
0.5909	Remote Similarity	NPD7110	Phase 1
0.5902	Remote Similarity	NPD7015	Phase 2
0.5902	Remote Similarity	NPD7016	Phase 3
0.5896	Remote Similarity	NPD3647	Clinical (unspecified phase)
0.5886	Remote Similarity	NPD7261	Clinical (unspecified phase)
0.5886	Remote Similarity	NPD2230	Approved
0.5886	Remote Similarity	NPD2232	Approved
0.5886	Remote Similarity	NPD2233	Approved
0.5882	Remote Similarity	NPD6658	Clinical (unspecified phase)
0.5876	Remote Similarity	NPD7298	Approved
0.5876	Remote Similarity	NPD5720	Discontinued
0.5872	Remote Similarity	NPD3124	Discontinued
0.586	Remote Similarity	NPD1671	Clinical (unspecified phase)
0.5854	Remote Similarity	NPD2245	Discovery
0.5849	Remote Similarity	NPD1420	Approved
0.5849	Remote Similarity	NPD1421	Approved
0.5849	Remote Similarity	NPD1669	Approved
0.5843	Remote Similarity	NPD6818	Clinical (unspecified phase)
0.5838	Remote Similarity	NPD4123	Phase 3
0.5838	Remote Similarity	NPD6322	Clinical (unspecified phase)
0.5833	Remote Similarity	NPD7833	Phase 2
0.5833	Remote Similarity	NPD7832	Clinical (unspecified phase)
0.5833	Remote Similarity	NPD7831	Phase 2
0.5823	Remote Similarity	NPD3705	Approved
0.5818	Remote Similarity	NPD2238	Phase 2
0.5817	Remote Similarity	NPD595	Approved
0.5817	Remote Similarity	NPD593	Approved
0.5813	Remote Similarity	NPD2922	Phase 1
0.5795	Remote Similarity	NPD824	Approved
0.5792	Remote Similarity	NPD4166	Phase 2
0.5792	Remote Similarity	NPD6071	Discontinued
0.5792	Remote Similarity	NPD3051	Approved
0.578	Remote Similarity	NPD1786	Approved
0.578	Remote Similarity	NPD1787	Approved
0.578	Remote Similarity	NPD5297	Approved
0.578	Remote Similarity	NPD1785	Approved
0.5778	Remote Similarity	NPD6788	Approved
0.5774	Remote Similarity	NPD3693	Clinical (unspecified phase)
0.5774	Remote Similarity	NPD3152	Clinical (unspecified phase)
0.5771	Remote Similarity	NPD5976	Discontinued
0.5761	Remote Similarity	NPD2970	Approved
0.5761	Remote Similarity	NPD2969	Approved
0.5758	Remote Similarity	NPD3531	Approved
0.5758	Remote Similarity	NPD3532	Approved
0.5758	Remote Similarity	NPD3530	Approved
0.5746	Remote Similarity	NPD5604	Discontinued
0.5736	Remote Similarity	NPD5564	Approved
0.5732	Remote Similarity	NPD1357	Approved
0.5731	Remote Similarity	NPD3599	Approved
0.573	Remote Similarity	NPD4481	Phase 3
0.573	Remote Similarity	NPD6873	Phase 2
0.573	Remote Similarity	NPD27	Approved
0.573	Remote Similarity	NPD6385	Approved
0.573	Remote Similarity	NPD6386	Approved
0.573	Remote Similarity	NPD2489	Approved
0.5723	Remote Similarity	NPD3110	Approved
0.5723	Remote Similarity	NPD3109	Approved
0.5722	Remote Similarity	NPD5977	Approved
0.5722	Remote Similarity	NPD5978	Approved
0.5714	Remote Similarity	NPD1349	Approved
0.5714	Remote Similarity	NPD1351	Approved
0.5714	Remote Similarity	NPD6493	Phase 3
0.5714	Remote Similarity	NPD1350	Approved
0.5714	Remote Similarity	NPD7258	Clinical (unspecified phase)
0.5707	Remote Similarity	NPD4483	Discontinued
0.5706	Remote Similarity	NPD2040	Clinical (unspecified phase)
0.5697	Remote Similarity	NPD1039	Discontinued
0.5697	Remote Similarity	NPD6812	Clinical (unspecified phase)
0.5683	Remote Similarity	NPD7201	Clinical (unspecified phase)
0.5679	Remote Similarity	NPD3055	Approved
0.5679	Remote Similarity	NPD4098	Discontinued
0.5679	Remote Similarity	NPD3053	Approved
0.5674	Remote Similarity	NPD1337	Clinical (unspecified phase)
0.5674	Remote Similarity	NPD4678	Approved
0.5674	Remote Similarity	NPD4675	Approved
0.5669	Remote Similarity	NPD2486	Discontinued
0.5667	Remote Similarity	NPD4585	Approved
0.5667	Remote Similarity	NPD6064	Phase 1
0.5663	Remote Similarity	NPD1726	Clinical (unspecified phase)
0.5655	Remote Similarity	NPD4579	Clinical (unspecified phase)
0.5652	Remote Similarity	NPD3676	Clinical (unspecified phase)
0.5652	Remote Similarity	NPD6107	Approved
0.5647	Remote Similarity	NPD3539	Phase 1
0.5645	Remote Similarity	NPD2898	Approved
0.5644	Remote Similarity	NPD558	Phase 2
0.5644	Remote Similarity	NPD6584	Phase 3
0.5644	Remote Similarity	NPD9619	Approved
0.5644	Remote Similarity	NPD7018	Phase 2
0.5644	Remote Similarity	NPD9621	Approved
0.5644	Remote Similarity	NPD9620	Approved
0.5641	Remote Similarity	NPD3596	Phase 2
0.5636	Remote Similarity	NPD5746	Approved
0.5625	Remote Similarity	NPD52	Approved
0.5625	Remote Similarity	NPD7526	Approved
0.5625	Remote Similarity	NPD7527	Clinical (unspecified phase)
0.5622	Remote Similarity	NPD4010	Discontinued
0.5618	Remote Similarity	NPD4005	Discontinued
0.5617	Remote Similarity	NPD5310	Approved
0.5617	Remote Similarity	NPD5311	Approved
0.5617	Remote Similarity	NPD9634	Clinical (unspecified phase)
0.5614	Remote Similarity	NPD3540	Phase 1
0.5611	Remote Similarity	NPD7945	Clinical (unspecified phase)
0.561	Remote Similarity	NPD1712	Approved
0.5607	Remote Similarity	NPD5754	Discontinued
0.5605	Remote Similarity	NPD5536	Phase 2
0.5604	Remote Similarity	NPD3674	Clinical (unspecified phase)
0.5602	Remote Similarity	NPD598	Approved
0.5602	Remote Similarity	NPD5111	Phase 2
0.5602	Remote Similarity	NPD5110	Phase 2
0.5602	Remote Similarity	NPD601	Approved
0.5602	Remote Similarity	NPD597	Approved
0.5602	Remote Similarity	NPD5109	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