NPASS Compound

Structure

NPC28414 OpenBabel07101718332D 36 38 0 0 0 0 0 0 0 0999 V2000 -1.7321 -5.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -5.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -5.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -5.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -4.5000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -4.5000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -2.0000 0.0000 S 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -2.0000 0.0000 S 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -2.0000 0.0000 S 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 S 0 0 0 0 0 0 0 0 0 0 0 0 1 27 1 0 0 0 0 2 27 1 0 0 0 0 3 28 1 0 0 0 0 4 28 1 0 0 0 0 5 29 1 0 0 0 0 6 30 1 0 0 0 0 7 31 1 0 0 0 0 8 32 1 0 0 0 0 9 33 1 0 0 0 0 10 34 1 0 0 0 0 11 13 1 0 0 0 0 11 15 1 0 0 0 0 12 14 1 0 0 0 0 12 16 1 0 0 0 0 13 27 1 0 0 0 0 14 28 1 0 0 0 0 15 21 2 0 0 0 0 15 23 1 0 0 0 0 16 22 2 0 0 0 0 16 24 1 0 0 0 0 17 19 2 0 0 0 0 17 21 1 0 0 0 0 17 29 1 0 0 0 0 18 20 2 0 0 0 0 18 22 1 0 0 0 0 18 30 1 0 0 0 0 19 25 1 0 0 0 0 19 31 1 0 0 0 0 20 26 1 0 0 0 0 20 32 1 0 0 0 0 21 33 1 0 0 0 0 22 34 1 0 0 0 0 23 25 2 0 0 0 0 23 35 1 0 0 0 0 24 26 2 0 0 0 0 24 35 1 0 0 0 0 25 36 1 0 0 0 0 26 36 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	570.17
Volume:	547.954
LogP:	4.45
LogD:	3.133
LogS:	-4.939
# Rotatable Bonds:	12
TPSA:	43.4
# H-Bond Aceptor:	6
# H-Bond Donor:	0
# Rings:	3
# Heavy Atoms:	10

MedChem Properties

QED Drug-Likeness Score:	0.243
Synthetic Accessibility Score:	3.694
Fsp3:	0.538
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:	-4.978
MDCK Permeability:	3.9061138522811234e-05
Pgp-inhibitor:	0.968
Pgp-substrate:	0.998
Human Intestinal Absorption (HIA):	0.955
20% Bioavailability (F20%):	0.001
30% Bioavailability (F30%):	0.028

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.948
Plasma Protein Binding (PPB):	91.96430969238281%
Volume Distribution (VD):	1.408
Pgp-substrate:	8.089204788208008%

ADMET: Metabolism

CYP1A2-inhibitor:	0.475
CYP1A2-substrate:	0.993
CYP2C19-inhibitor:	0.022
CYP2C19-substrate:	0.992
CYP2C9-inhibitor:	0.0
CYP2C9-substrate:	0.947
CYP2D6-inhibitor:	0.029
CYP2D6-substrate:	0.96
CYP3A4-inhibitor:	0.105
CYP3A4-substrate:	0.944

ADMET: Excretion

Clearance (CL):	7.43
Half-life (T1/2):	0.121

ADMET: Toxicity

hERG Blockers:	0.179
Human Hepatotoxicity (H-HT):	0.317
Drug-inuced Liver Injury (DILI):	0.95
AMES Toxicity:	0.055
Rat Oral Acute Toxicity:	0.991
Maximum Recommended Daily Dose:	0.103
Skin Sensitization:	0.083
Carcinogencity:	0.027
Eye Corrosion:	0.003
Eye Irritation:	0.012
Respiratory Toxicity:	0.971

Download Data

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

Natural Product: NPC28414

Natural Product ID:	NPC28414
*Common Name:**	Lissoclinotoxin E
IUPAC Name:	2-[9-[2-(dimethylamino)ethyl]-3,4,6,7-tetramethoxy-2,8-bis(methylsulfanyl)thianthren-1-yl]-N,N-dimethylethanamine
Synonyms:	Lissoclinotoxin E
Standard InCHIKey:	RKXCFLRMPUNAQQ-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C26H38N2O4S4/c1-27(2)13-11-15-21(33-9)17(29-5)19(31-7)25-23(15)35-24-16(12-14-28(3)4)22(34-10)18(30-6)20(32-8)26(24)36-25/h11-14H2,1-10H3
SMILES:	CN(C)CCc1c(c(c(c2c1Sc1c(CCN(C)C)c(c(c(c1S2)OC)OC)SC)OC)OC)SC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL375626
PubChem CID:	12192125
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0002804] Benzodithiins [CHEMONTID:0002807] 1,4-benzodithiins [CHEMONTID:0002803] Thianthrenes

*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]

☑ 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

Activity Type	# Activity
NON-MOLECULAR	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	EC50	=	270.0	nM	PMID[479535]

☑ 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 NPC28414 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	380
0.1-0.2	3651
0.2-0.3	15213
0.3-0.4	7095
0.4-0.5	12985
0.5-0.6	3116
0.6-0.7	236
0.7-0.8	8
0.8-0.85	3
0.85-0.9	1
0.9-0.95	7
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC298924
0.9658	High Similarity	NPC291583
0.9658	High Similarity	NPC191200
0.953	High Similarity	NPC257143
0.911	High Similarity	NPC226601
0.911	High Similarity	NPC69623
0.9103	High Similarity	NPC130921
0.8868	High Similarity	NPC177023
0.8428	Intermediate Similarity	NPC94292
0.8176	Intermediate Similarity	NPC131440
0.8105	Intermediate Similarity	NPC261940
0.7736	Intermediate Similarity	NPC296858
0.7564	Intermediate Similarity	NPC59661
0.7532	Intermediate Similarity	NPC474553
0.7468	Intermediate Similarity	NPC475698
0.7391	Intermediate Similarity	NPC474649
0.7391	Intermediate Similarity	NPC474652
0.6937	Remote Similarity	NPC42793
0.6937	Remote Similarity	NPC231884
0.6937	Remote Similarity	NPC167944
0.6875	Remote Similarity	NPC11147
0.6859	Remote Similarity	NPC172403
0.6768	Remote Similarity	NPC188163
0.6768	Remote Similarity	NPC474915
0.6768	Remote Similarity	NPC328750
0.6768	Remote Similarity	NPC213206
0.6723	Remote Similarity	NPC206941
0.6707	Remote Similarity	NPC314682
0.6687	Remote Similarity	NPC476567
0.6687	Remote Similarity	NPC128019
0.6687	Remote Similarity	NPC118419
0.6687	Remote Similarity	NPC136860
0.6667	Remote Similarity	NPC160193
0.6667	Remote Similarity	NPC323204
0.6645	Remote Similarity	NPC298486
0.6628	Remote Similarity	NPC206372
0.6628	Remote Similarity	NPC203424
0.6582	Remote Similarity	NPC301713
0.6529	Remote Similarity	NPC51957
0.6529	Remote Similarity	NPC210437
0.6529	Remote Similarity	NPC476144
0.6529	Remote Similarity	NPC106295
0.6529	Remote Similarity	NPC16107
0.6509	Remote Similarity	NPC185838
0.6491	Remote Similarity	NPC475959
0.6491	Remote Similarity	NPC476571
0.6491	Remote Similarity	NPC147390
0.6491	Remote Similarity	NPC428
0.6491	Remote Similarity	NPC24233
0.6491	Remote Similarity	NPC7467
0.6491	Remote Similarity	NPC130941
0.6491	Remote Similarity	NPC135538
0.6491	Remote Similarity	NPC246587
0.6485	Remote Similarity	NPC193528
0.6481	Remote Similarity	NPC214869
0.6457	Remote Similarity	NPC187022
0.6457	Remote Similarity	NPC80129
0.6433	Remote Similarity	NPC179825
0.6433	Remote Similarity	NPC191376
0.6433	Remote Similarity	NPC321505
0.6433	Remote Similarity	NPC476151
0.642	Remote Similarity	NPC247639
0.642	Remote Similarity	NPC114102
0.642	Remote Similarity	NPC25084
0.642	Remote Similarity	NPC476570
0.6416	Remote Similarity	NPC192768
0.6416	Remote Similarity	NPC88249
0.6416	Remote Similarity	NPC151895
0.6416	Remote Similarity	NPC220858
0.6416	Remote Similarity	NPC97221
0.6413	Remote Similarity	NPC20395
0.6412	Remote Similarity	NPC145304
0.6379	Remote Similarity	NPC476568
0.6374	Remote Similarity	NPC473934
0.6364	Remote Similarity	NPC120075
0.6358	Remote Similarity	NPC477565
0.6358	Remote Similarity	NPC219162
0.6358	Remote Similarity	NPC262641
0.6358	Remote Similarity	NPC52029
0.6358	Remote Similarity	NPC211296
0.6358	Remote Similarity	NPC35961
0.6358	Remote Similarity	NPC103379
0.6358	Remote Similarity	NPC195749
0.6358	Remote Similarity	NPC92541
0.6348	Remote Similarity	NPC216816
0.6348	Remote Similarity	NPC186595
0.6343	Remote Similarity	NPC210148
0.6343	Remote Similarity	NPC233029
0.6341	Remote Similarity	NPC160692
0.6325	Remote Similarity	NPC301050
0.6325	Remote Similarity	NPC7018
0.6325	Remote Similarity	NPC416184
0.6325	Remote Similarity	NPC131204
0.6316	Remote Similarity	NPC110337
0.6316	Remote Similarity	NPC130926
0.6313	Remote Similarity	NPC46067
0.6296	Remote Similarity	NPC155838
0.6287	Remote Similarity	NPC253429
0.6286	Remote Similarity	NPC326316
0.6286	Remote Similarity	NPC85747
0.6286	Remote Similarity	NPC8337
0.6286	Remote Similarity	NPC81733
0.6271	Remote Similarity	NPC469817
0.6271	Remote Similarity	NPC110416
0.6271	Remote Similarity	NPC39701
0.6271	Remote Similarity	NPC278799
0.6271	Remote Similarity	NPC127674
0.6271	Remote Similarity	NPC276588
0.6271	Remote Similarity	NPC54379
0.6271	Remote Similarity	NPC5238
0.6271	Remote Similarity	NPC189266
0.6271	Remote Similarity	NPC138487
0.6271	Remote Similarity	NPC193949
0.6271	Remote Similarity	NPC216459
0.6271	Remote Similarity	NPC204828
0.6271	Remote Similarity	NPC325871
0.6271	Remote Similarity	NPC41178
0.6271	Remote Similarity	NPC93593
0.6271	Remote Similarity	NPC249797
0.6271	Remote Similarity	NPC184026
0.6271	Remote Similarity	NPC244112
0.6271	Remote Similarity	NPC99659
0.6271	Remote Similarity	NPC295691
0.6271	Remote Similarity	NPC207757
0.6271	Remote Similarity	NPC172765
0.6271	Remote Similarity	NPC2413
0.6265	Remote Similarity	NPC475828
0.6264	Remote Similarity	NPC207824
0.6264	Remote Similarity	NPC60538
0.625	Remote Similarity	NPC210086
0.6243	Remote Similarity	NPC115144
0.6243	Remote Similarity	NPC277857
0.6243	Remote Similarity	NPC144863
0.6243	Remote Similarity	NPC90844
0.6243	Remote Similarity	NPC253883
0.6243	Remote Similarity	NPC95075
0.6243	Remote Similarity	NPC475393
0.6236	Remote Similarity	NPC186063
0.6236	Remote Similarity	NPC146288
0.6235	Remote Similarity	NPC222039
0.6235	Remote Similarity	NPC153990
0.6235	Remote Similarity	NPC100478
0.6235	Remote Similarity	NPC186898
0.6235	Remote Similarity	NPC251571
0.6234	Remote Similarity	NPC47194
0.6229	Remote Similarity	NPC13397
0.6221	Remote Similarity	NPC5462
0.6209	Remote Similarity	NPC165106
0.6209	Remote Similarity	NPC284183
0.6209	Remote Similarity	NPC4138
0.6209	Remote Similarity	NPC121275
0.6201	Remote Similarity	NPC476572
0.6194	Remote Similarity	NPC9341
0.6194	Remote Similarity	NPC81067
0.6193	Remote Similarity	NPC476579
0.6193	Remote Similarity	NPC277669
0.6193	Remote Similarity	NPC76213
0.619	Remote Similarity	NPC204848
0.619	Remote Similarity	NPC41473
0.619	Remote Similarity	NPC312770
0.619	Remote Similarity	NPC14600
0.619	Remote Similarity	NPC160607
0.6175	Remote Similarity	NPC256012
0.6175	Remote Similarity	NPC317272
0.6175	Remote Similarity	NPC268503
0.6175	Remote Similarity	NPC42549
0.6175	Remote Similarity	NPC240841
0.6175	Remote Similarity	NPC250846
0.6167	Remote Similarity	NPC111485
0.6158	Remote Similarity	NPC476580
0.6158	Remote Similarity	NPC114124
0.6154	Remote Similarity	NPC231572
0.6154	Remote Similarity	NPC299583
0.6149	Remote Similarity	NPC105513
0.6145	Remote Similarity	NPC234392
0.6145	Remote Similarity	NPC313737
0.6145	Remote Similarity	NPC285078
0.6145	Remote Similarity	NPC6854
0.6145	Remote Similarity	NPC31311
0.6139	Remote Similarity	NPC321133
0.6136	Remote Similarity	NPC274026
0.6129	Remote Similarity	NPC473264
0.6129	Remote Similarity	NPC475815
0.6124	Remote Similarity	NPC2295
0.6124	Remote Similarity	NPC292003
0.6124	Remote Similarity	NPC475557
0.6124	Remote Similarity	NPC477564
0.6108	Remote Similarity	NPC66573
0.6099	Remote Similarity	NPC60186
0.6095	Remote Similarity	NPC220923
0.6095	Remote Similarity	NPC252107
0.6087	Remote Similarity	NPC140359
0.6087	Remote Similarity	NPC13020
0.6084	Remote Similarity	NPC93882
0.6084	Remote Similarity	NPC130595
0.6077	Remote Similarity	NPC477080
0.6076	Remote Similarity	NPC474320
0.6075	Remote Similarity	NPC109925
0.6067	Remote Similarity	NPC82285
0.6067	Remote Similarity	NPC148898

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 NPC28414 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	217
0.1-0.2	1066
0.2-0.3	1880
0.3-0.4	3180
0.4-0.5	2025
0.5-0.6	704
0.6-0.7	75
0.7-0.8	3
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
0.7273	Intermediate Similarity	NPD5718	Phase 2
0.7151	Intermediate Similarity	NPD7802	Discontinued
0.7143	Intermediate Similarity	NPD5708	Clinical (unspecified phase)
0.7032	Intermediate Similarity	NPD5752	Clinical (unspecified phase)
0.6937	Remote Similarity	NPD6895	Approved
0.6937	Remote Similarity	NPD6896	Approved
0.6914	Remote Similarity	NPD5085	Clinical (unspecified phase)
0.6768	Remote Similarity	NPD4664	Clinical (unspecified phase)
0.6687	Remote Similarity	NPD6029	Clinical (unspecified phase)
0.6687	Remote Similarity	NPD6028	Clinical (unspecified phase)
0.6686	Remote Similarity	NPD1757	Discontinued
0.6628	Remote Similarity	NPD4179	Approved
0.6628	Remote Similarity	NPD4180	Approved
0.6607	Remote Similarity	NPD7124	Phase 2
0.657	Remote Similarity	NPD6055	Clinical (unspecified phase)
0.6562	Remote Similarity	NPD2669	Clinical (unspecified phase)
0.6529	Remote Similarity	NPD4584	Approved
0.6519	Remote Similarity	NPD730	Discontinued
0.6494	Remote Similarity	NPD7110	Phase 1
0.6494	Remote Similarity	NPD7109	Clinical (unspecified phase)
0.6491	Remote Similarity	NPD2236	Approved
0.6477	Remote Similarity	NPD6374	Clinical (unspecified phase)
0.6457	Remote Similarity	NPD7298	Approved
0.6453	Remote Similarity	NPD6662	Clinical (unspecified phase)
0.645	Remote Similarity	NPD5241	Discontinued
0.6437	Remote Similarity	NPD1642	Discontinued
0.6433	Remote Similarity	NPD4739	Approved
0.6429	Remote Similarity	NPD4162	Approved
0.6429	Remote Similarity	NPD3060	Approved
0.642	Remote Similarity	NPD487	Discontinued
0.6412	Remote Similarity	NPD6066	Clinical (unspecified phase)
0.6412	Remote Similarity	NPD6783	Clinical (unspecified phase)
0.6375	Remote Similarity	NPD7905	Discontinued
0.6358	Remote Similarity	NPD6030	Approved
0.6358	Remote Similarity	NPD6031	Approved
0.6353	Remote Similarity	NPD5084	Clinical (unspecified phase)
0.6343	Remote Similarity	NPD6876	Approved
0.6343	Remote Similarity	NPD6875	Approved
0.6337	Remote Similarity	NPD6322	Clinical (unspecified phase)
0.6329	Remote Similarity	NPD1244	Clinical (unspecified phase)
0.6328	Remote Similarity	NPD6818	Clinical (unspecified phase)
0.6316	Remote Similarity	NPD5188	Clinical (unspecified phase)
0.6296	Remote Similarity	NPD5087	Clinical (unspecified phase)
0.6294	Remote Similarity	NPD6658	Clinical (unspecified phase)
0.6286	Remote Similarity	NPD7261	Clinical (unspecified phase)
0.6286	Remote Similarity	NPD4017	Approved
0.6265	Remote Similarity	NPD2653	Approved
0.6257	Remote Similarity	NPD3075	Approved
0.6235	Remote Similarity	NPD5177	Phase 3
0.6228	Remote Similarity	NPD6111	Discontinued
0.6209	Remote Similarity	NPD5283	Phase 1
0.6207	Remote Similarity	NPD6890	Discontinued
0.6196	Remote Similarity	NPD7016	Phase 3
0.6196	Remote Similarity	NPD7015	Phase 2
0.6182	Remote Similarity	NPD554	Clinical (unspecified phase)
0.618	Remote Similarity	NPD7945	Clinical (unspecified phase)
0.618	Remote Similarity	NPD5720	Discontinued
0.6171	Remote Similarity	NPD3639	Approved
0.6171	Remote Similarity	NPD3640	Phase 3
0.6171	Remote Similarity	NPD3641	Approved
0.6167	Remote Similarity	NPD6788	Approved
0.6163	Remote Similarity	NPD5307	Clinical (unspecified phase)
0.6154	Remote Similarity	NPD2644	Approved
0.6149	Remote Similarity	NPD2922	Phase 1
0.6149	Remote Similarity	NPD4123	Phase 3
0.6149	Remote Similarity	NPD7258	Clinical (unspecified phase)
0.614	Remote Similarity	NPD4236	Phase 3
0.614	Remote Similarity	NPD4237	Approved
0.6139	Remote Similarity	NPD2667	Approved
0.6139	Remote Similarity	NPD2668	Approved
0.6124	Remote Similarity	NPD6873	Phase 2
0.6124	Remote Similarity	NPD4772	Phase 2
0.6124	Remote Similarity	NPD4773	Phase 2
0.6105	Remote Similarity	NPD6331	Phase 2
0.6092	Remote Similarity	NPD3124	Discontinued
0.6084	Remote Similarity	NPD3531	Approved
0.6084	Remote Similarity	NPD3530	Approved
0.6084	Remote Similarity	NPD2674	Phase 3
0.6084	Remote Similarity	NPD3532	Approved
0.6066	Remote Similarity	NPD7201	Clinical (unspecified phase)
0.6057	Remote Similarity	NPD1424	Approved
0.6056	Remote Similarity	NPD5563	Clinical (unspecified phase)
0.6056	Remote Similarity	NPD5772	Approved
0.6056	Remote Similarity	NPD5773	Approved
0.6044	Remote Similarity	NPD7833	Phase 2
0.6044	Remote Similarity	NPD7831	Phase 2
0.6044	Remote Similarity	NPD7832	Clinical (unspecified phase)
0.6043	Remote Similarity	NPD8252	Approved
0.6043	Remote Similarity	NPD8099	Discontinued
0.6043	Remote Similarity	NPD8251	Approved
0.6034	Remote Similarity	NPD6386	Approved
0.6034	Remote Similarity	NPD6385	Approved
0.6033	Remote Similarity	NPD6107	Approved
0.6023	Remote Similarity	NPD3647	Clinical (unspecified phase)
0.6012	Remote Similarity	NPD4098	Discontinued
0.6011	Remote Similarity	NPD8156	Discontinued
0.6011	Remote Similarity	NPD746	Clinical (unspecified phase)
0.6	Remote Similarity	NPD1671	Clinical (unspecified phase)
0.6	Remote Similarity	NPD3693	Clinical (unspecified phase)
0.6	Remote Similarity	NPD4010	Discontinued
0.599	Remote Similarity	NPD6493	Phase 3
0.599	Remote Similarity	NPD4483	Discontinued
0.5989	Remote Similarity	NPD2901	Approved
0.5989	Remote Similarity	NPD2900	Approved
0.5988	Remote Similarity	NPD7153	Discontinued
0.5978	Remote Similarity	NPD5677	Discontinued
0.5978	Remote Similarity	NPD4675	Approved
0.5978	Remote Similarity	NPD4678	Approved
0.5976	Remote Similarity	NPD2492	Phase 1
0.5975	Remote Similarity	NPD6382	Discontinued
0.5968	Remote Similarity	NPD6687	Approved
0.5968	Remote Similarity	NPD6688	Approved
0.5967	Remote Similarity	NPD2978	Approved
0.5967	Remote Similarity	NPD7089	Clinical (unspecified phase)
0.5967	Remote Similarity	NPD2977	Approved
0.5966	Remote Similarity	NPD1754	Clinical (unspecified phase)
0.5956	Remote Similarity	NPD5604	Discontinued
0.5955	Remote Similarity	NPD4210	Discontinued
0.5952	Remote Similarity	NPD3110	Approved
0.5952	Remote Similarity	NPD3109	Approved
0.5951	Remote Similarity	NPD5311	Approved
0.5951	Remote Similarity	NPD5310	Approved
0.5941	Remote Similarity	NPD7590	Clinical (unspecified phase)
0.5934	Remote Similarity	NPD5977	Approved
0.5934	Remote Similarity	NPD5978	Approved
0.593	Remote Similarity	NPD1803	Phase 3
0.5928	Remote Similarity	NPD3145	Approved
0.5928	Remote Similarity	NPD5111	Phase 2
0.5928	Remote Similarity	NPD6812	Clinical (unspecified phase)
0.5928	Remote Similarity	NPD3144	Approved
0.5928	Remote Similarity	NPD5110	Phase 2
0.5928	Remote Similarity	NPD5109	Approved
0.5926	Remote Similarity	NPD2233	Approved
0.5926	Remote Similarity	NPD2232	Approved
0.5926	Remote Similarity	NPD2230	Approved
0.5922	Remote Similarity	NPD6813	Clinical (unspecified phase)
0.5922	Remote Similarity	NPD4005	Discontinued
0.5914	Remote Similarity	NPD6071	Discontinued
0.5904	Remote Similarity	NPD5602	Clinical (unspecified phase)
0.5896	Remote Similarity	NPD1044	Clinical (unspecified phase)
0.589	Remote Similarity	NPD1669	Approved
0.5882	Remote Similarity	NPD4579	Clinical (unspecified phase)
0.5879	Remote Similarity	NPD6064	Phase 1
0.5879	Remote Similarity	NPD6584	Phase 3
0.5879	Remote Similarity	NPD1006	Clinical (unspecified phase)
0.5876	Remote Similarity	NPD1771	Clinical (unspecified phase)
0.5875	Remote Similarity	NPD6830	Clinical (unspecified phase)
0.5872	Remote Similarity	NPD3539	Phase 1
0.5872	Remote Similarity	NPD2161	Phase 2
0.5866	Remote Similarity	NPD3687	Approved
0.5866	Remote Similarity	NPD3686	Approved
0.5864	Remote Similarity	NPD6297	Approved
0.5864	Remote Similarity	NPD2759	Clinical (unspecified phase)
0.5858	Remote Similarity	NPD2238	Phase 2
0.5851	Remote Similarity	NPD4481	Phase 3
0.585	Remote Similarity	NPD7034	Discontinued
0.5849	Remote Similarity	NPD5536	Phase 2
0.5842	Remote Similarity	NPD5312	Approved
0.5842	Remote Similarity	NPD5313	Approved
0.5838	Remote Similarity	NPD1375	Discontinued
0.5838	Remote Similarity	NPD3540	Phase 1
0.5829	Remote Similarity	NPD3051	Approved
0.5829	Remote Similarity	NPD4166	Phase 2
0.5825	Remote Similarity	NPD6853	Approved
0.5825	Remote Similarity	NPD6851	Approved
0.5825	Remote Similarity	NPD6618	Phase 2
0.5825	Remote Similarity	NPD8053	Approved
0.5825	Remote Similarity	NPD8054	Approved
0.5824	Remote Similarity	NPD3657	Discovery
0.5819	Remote Similarity	NPD5297	Approved
0.5818	Remote Similarity	NPD3055	Approved
0.5818	Remote Similarity	NPD3053	Approved
0.5814	Remote Similarity	NPD3152	Clinical (unspecified phase)
0.5813	Remote Similarity	NPD6580	Approved
0.5813	Remote Similarity	NPD2486	Discontinued
0.5813	Remote Similarity	NPD6581	Approved
0.581	Remote Similarity	NPD2122	Discontinued
0.5799	Remote Similarity	NPD2245	Discovery
0.5799	Remote Similarity	NPD4474	Approved
0.5799	Remote Similarity	NPD4475	Approved
0.5798	Remote Similarity	NPD2970	Approved
0.5798	Remote Similarity	NPD2969	Approved
0.5795	Remote Similarity	NPD6990	Approved
0.5795	Remote Similarity	NPD6989	Approved
0.5789	Remote Similarity	NPD5314	Approved
0.5786	Remote Similarity	NPD3596	Phase 2
0.5784	Remote Similarity	NPD7975	Clinical (unspecified phase)
0.5771	Remote Similarity	NPD3599	Approved
0.5771	Remote Similarity	NPD5564	Approved
0.5767	Remote Similarity	NPD27	Approved
0.5767	Remote Similarity	NPD2489	Approved
0.5765	Remote Similarity	NPD4101	Phase 1
0.5763	Remote Similarity	NPD6106	Discontinued
0.5761	Remote Similarity	NPD2563	Approved
0.5761	Remote Similarity	NPD2560	Approved
0.5761	Remote Similarity	NPD7494	Clinical (unspecified phase)
0.5754	Remote Similarity	NPD52	Approved
0.5754	Remote Similarity	NPD5261	Clinical (unspecified phase)
0.5754	Remote Similarity	NPD7527	Clinical (unspecified phase)
0.5754	Remote Similarity	NPD7526	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