NPASS Compound

Structure

NPC131440 OpenBabel07101719522D 32 34 0 0 0 0 0 0 0 0999 V2000 1.5731 -5.2071 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3052 -5.2071 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5731 2.7929 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3052 2.7929 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3052 0.7929 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1712 -1.7071 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5731 -3.2071 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5731 0.7929 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4392 -3.7071 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4392 1.2929 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4392 -1.7071 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4392 -0.7071 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5731 -2.2071 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5731 -0.2071 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4392 -0.7071 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4392 -1.7071 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5731 -0.2071 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5731 -2.2071 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7071 -1.7071 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7071 -0.7071 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7071 -0.7071 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7071 -1.7071 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4392 -4.7071 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -3.4392 2.2929 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 1.5731 0.7929 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5731 -3.2071 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.3052 -0.2071 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.3052 -2.2071 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -2.4142 0.0000 S 0 0 0 0 0 0 0 0 0 0 0 0 -1.0000 0.0000 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 -1.0000 -2.4142 0.0000 S 0 0 0 0 0 0 0 0 0 0 0 0 1 23 1 0 0 0 0 2 23 1 0 0 0 0 3 24 1 0 0 0 0 4 24 1 0 0 0 0 5 27 1 0 0 0 0 6 28 1 0 0 0 0 7 9 1 0 0 0 0 7 13 1 0 0 0 0 8 10 1 0 0 0 0 8 14 1 0 0 0 0 9 23 1 0 0 0 0 10 24 1 0 0 0 0 11 13 2 0 0 0 0 11 15 1 0 0 0 0 12 14 2 0 0 0 0 12 16 1 0 0 0 0 13 19 1 0 0 0 0 14 20 1 0 0 0 0 15 17 2 0 0 0 0 15 27 1 0 0 0 0 16 18 2 0 0 0 0 16 28 1 0 0 0 0 17 21 1 0 0 0 0 17 25 1 0 0 0 0 18 22 1 0 0 0 0 18 26 1 0 0 0 0 19 21 2 0 0 0 0 19 29 1 0 0 0 0 20 22 2 0 0 0 0 20 30 1 0 0 0 0 21 31 1 0 0 0 0 22 32 1 0 0 0 0 29 32 1 0 0 0 0 30 31 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	514.11
Volume:	478.771
LogP:	4.017
LogD:	3.003
LogS:	-4.907
# Rotatable Bonds:	8
TPSA:	65.4
# H-Bond Aceptor:	6
# H-Bond Donor:	2
# Rings:	3
# Heavy Atoms:	10

MedChem Properties

QED Drug-Likeness Score:	0.458
Synthetic Accessibility Score:	3.646
Fsp3:	0.455
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	1
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.14
MDCK Permeability:	1.0872794518945739e-05
Pgp-inhibitor:	0.808
Pgp-substrate:	0.966
Human Intestinal Absorption (HIA):	0.04
20% Bioavailability (F20%):	0.008
30% Bioavailability (F30%):	0.029

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.859
Plasma Protein Binding (PPB):	92.4712142944336%
Volume Distribution (VD):	1.774
Pgp-substrate:	14.697188377380371%

ADMET: Metabolism

CYP1A2-inhibitor:	0.439
CYP1A2-substrate:	0.963
CYP2C19-inhibitor:	0.577
CYP2C19-substrate:	0.954
CYP2C9-inhibitor:	0.073
CYP2C9-substrate:	0.799
CYP2D6-inhibitor:	0.297
CYP2D6-substrate:	0.946
CYP3A4-inhibitor:	0.033
CYP3A4-substrate:	0.707

ADMET: Excretion

Clearance (CL):	11.056
Half-life (T1/2):	0.213

ADMET: Toxicity

hERG Blockers:	0.126
Human Hepatotoxicity (H-HT):	0.309
Drug-inuced Liver Injury (DILI):	0.965
AMES Toxicity:	0.237
Rat Oral Acute Toxicity:	0.796
Maximum Recommended Daily Dose:	0.653
Skin Sensitization:	0.919
Carcinogencity:	0.026
Eye Corrosion:	0.057
Eye Irritation:	0.025
Respiratory Toxicity:	0.979

Download Data

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

Natural Product: NPC131440

Natural Product ID:	NPC131440
*Common Name:**	Lissoclibadin 7
IUPAC Name:	4,10-bis[2-(dimethylamino)ethyl]-2,8-dimethoxybenzo[c][1,2,5,6]benzotetrathiocine-1,7-diol
Synonyms:	Lissoclibadin 7
Standard InCHIKey:	SYDGARHBWHZCIW-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C22H30N2O4S4/c1-23(2)9-7-13-11-15(27-5)17(25)21-19(13)29-32-22-18(26)16(28-6)12-14(8-10-24(3)4)20(22)30-31-21/h11-12,25-26H,7-10H2,1-6H3
SMILES:	COc1cc(CCN(C)C)c2c(c1O)SSc1c(SS2)c(O)c(cc1CCN(C)C)OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL223616
PubChem CID:	16116098
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]

☑ 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	2
Others	4

Activity Type	# Activity
Cell Line	1
CELL-LINE	1
NON-MOLECULAR	1
Organism	4

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT148	Cell Line	HCT-15	Homo sapiens	IC50	=	15700.0	nM	PMID[556093]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	IZ	=	13.1	mm	PMID[556092]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	IZ	=	9.4	mm	PMID[556092]
NPT19	Organism	Escherichia coli	Escherichia coli	IZ	=	9.9	mm	PMID[556092]
NPT312	Organism	Saccharomyces cerevisiae	Saccharomyces cerevisiae	IZ	=	16.8	mm	PMID[556092]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	EC50	=	170.0	nM	PMID[556092]
NPT20987	CELL-LINE	HeLa S3	Homo sapiens	IC50	=	14200.0	nM	PMID[556093]

☑ 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 NPC131440 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	277
0.1-0.2	2352
0.2-0.3	13380
0.3-0.4	6289
0.4-0.5	9124
0.5-0.6	8887
0.6-0.7	2196
0.7-0.8	176
0.8-0.85	9
0.85-0.9	3
0.9-0.95	3
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9346	High Similarity	NPC94292
0.9257	High Similarity	NPC296858
0.9057	High Similarity	NPC177023
0.8931	High Similarity	NPC130921
0.8421	Intermediate Similarity	NPC474553
0.8355	Intermediate Similarity	NPC475698
0.8258	Intermediate Similarity	NPC474652
0.8258	Intermediate Similarity	NPC474649
0.8239	Intermediate Similarity	NPC291583
0.8239	Intermediate Similarity	NPC191200
0.8224	Intermediate Similarity	NPC59661
0.8176	Intermediate Similarity	NPC298924
0.8176	Intermediate Similarity	NPC28414
0.8065	Intermediate Similarity	NPC261940
0.8037	Intermediate Similarity	NPC257143
0.7962	Intermediate Similarity	NPC69623
0.7962	Intermediate Similarity	NPC226601
0.7763	Intermediate Similarity	NPC214869
0.7697	Intermediate Similarity	NPC114102
0.7632	Intermediate Similarity	NPC52029
0.7632	Intermediate Similarity	NPC195749
0.7632	Intermediate Similarity	NPC35961
0.7566	Intermediate Similarity	NPC155838
0.75	Intermediate Similarity	NPC186898
0.75	Intermediate Similarity	NPC251571
0.75	Intermediate Similarity	NPC153990
0.7485	Intermediate Similarity	NPC246587
0.7485	Intermediate Similarity	NPC147390
0.7485	Intermediate Similarity	NPC476571
0.7485	Intermediate Similarity	NPC428
0.7485	Intermediate Similarity	NPC24233
0.7485	Intermediate Similarity	NPC135538
0.7452	Intermediate Similarity	NPC131204
0.7452	Intermediate Similarity	NPC301050
0.7434	Intermediate Similarity	NPC301713
0.7423	Intermediate Similarity	NPC321505
0.7423	Intermediate Similarity	NPC191376
0.7423	Intermediate Similarity	NPC179825
0.7405	Intermediate Similarity	NPC312770
0.7405	Intermediate Similarity	NPC160607
0.7405	Intermediate Similarity	NPC41473
0.7405	Intermediate Similarity	NPC14600
0.7405	Intermediate Similarity	NPC193528
0.7405	Intermediate Similarity	NPC204848
0.7394	Intermediate Similarity	NPC151895
0.7394	Intermediate Similarity	NPC97221
0.7394	Intermediate Similarity	NPC220858
0.7394	Intermediate Similarity	NPC192768
0.7394	Intermediate Similarity	NPC88249
0.7386	Intermediate Similarity	NPC172403
0.7358	Intermediate Similarity	NPC299583
0.7351	Intermediate Similarity	NPC13020
0.7351	Intermediate Similarity	NPC140359
0.7342	Intermediate Similarity	NPC167944
0.7342	Intermediate Similarity	NPC231884
0.7342	Intermediate Similarity	NPC42793
0.7333	Intermediate Similarity	NPC103379
0.7333	Intermediate Similarity	NPC477565
0.7308	Intermediate Similarity	NPC93882
0.7308	Intermediate Similarity	NPC130595
0.7301	Intermediate Similarity	NPC185838
0.7297	Intermediate Similarity	NPC470626
0.7278	Intermediate Similarity	NPC11147
0.7262	Intermediate Similarity	NPC475557
0.7261	Intermediate Similarity	NPC6854
0.7261	Intermediate Similarity	NPC313737
0.7261	Intermediate Similarity	NPC285078
0.725	Intermediate Similarity	NPC296898
0.725	Intermediate Similarity	NPC231572
0.723	Intermediate Similarity	NPC293619
0.7222	Intermediate Similarity	NPC222039
0.7222	Intermediate Similarity	NPC100478
0.7219	Intermediate Similarity	NPC193949
0.7219	Intermediate Similarity	NPC207757
0.7219	Intermediate Similarity	NPC5238
0.7219	Intermediate Similarity	NPC127674
0.7219	Intermediate Similarity	NPC204828
0.7219	Intermediate Similarity	NPC172765
0.7219	Intermediate Similarity	NPC469817
0.7219	Intermediate Similarity	NPC295691
0.7219	Intermediate Similarity	NPC2413
0.7219	Intermediate Similarity	NPC278799
0.7219	Intermediate Similarity	NPC39701
0.7219	Intermediate Similarity	NPC184026
0.7219	Intermediate Similarity	NPC110416
0.7219	Intermediate Similarity	NPC189266
0.7219	Intermediate Similarity	NPC276588
0.7219	Intermediate Similarity	NPC249797
0.7219	Intermediate Similarity	NPC54379
0.7215	Intermediate Similarity	NPC218530
0.7212	Intermediate Similarity	NPC476151
0.7212	Intermediate Similarity	NPC277857
0.7212	Intermediate Similarity	NPC115144
0.72	Intermediate Similarity	NPC242885
0.72	Intermediate Similarity	NPC56214
0.72	Intermediate Similarity	NPC227217
0.72	Intermediate Similarity	NPC232316
0.72	Intermediate Similarity	NPC117780
0.72	Intermediate Similarity	NPC95614
0.72	Intermediate Similarity	NPC165133
0.7195	Intermediate Similarity	NPC5462
0.7171	Intermediate Similarity	NPC298486
0.7152	Intermediate Similarity	NPC207613
0.7143	Intermediate Similarity	NPC76213
0.7143	Intermediate Similarity	NPC277669
0.7134	Intermediate Similarity	NPC255550
0.7134	Intermediate Similarity	NPC308885
0.7133	Intermediate Similarity	NPC310338
0.7133	Intermediate Similarity	NPC281298
0.7105	Intermediate Similarity	NPC470212
0.7105	Intermediate Similarity	NPC54872
0.7105	Intermediate Similarity	NPC262156
0.7105	Intermediate Similarity	NPC113865
0.7105	Intermediate Similarity	NPC184651
0.7105	Intermediate Similarity	NPC38996
0.7105	Intermediate Similarity	NPC343720
0.7105	Intermediate Similarity	NPC324571
0.7105	Intermediate Similarity	NPC473853
0.7105	Intermediate Similarity	NPC160380
0.7105	Intermediate Similarity	NPC312675
0.7101	Intermediate Similarity	NPC206372
0.7101	Intermediate Similarity	NPC203424
0.7093	Intermediate Similarity	NPC111485
0.7089	Intermediate Similarity	NPC118419
0.7076	Intermediate Similarity	NPC186063
0.707	Intermediate Similarity	NPC160193
0.7059	Intermediate Similarity	NPC477564
0.7059	Intermediate Similarity	NPC85488
0.7059	Intermediate Similarity	NPC2295
0.7055	Intermediate Similarity	NPC188163
0.7055	Intermediate Similarity	NPC474915
0.7055	Intermediate Similarity	NPC323204
0.7055	Intermediate Similarity	NPC213206
0.7055	Intermediate Similarity	NPC328750
0.703	Intermediate Similarity	NPC294249
0.7029	Intermediate Similarity	NPC4138
0.7029	Intermediate Similarity	NPC284183
0.7029	Intermediate Similarity	NPC121275
0.7025	Intermediate Similarity	NPC326599
0.7025	Intermediate Similarity	NPC329595
0.7024	Intermediate Similarity	NPC207824
0.7024	Intermediate Similarity	NPC60538
0.7013	Intermediate Similarity	NPC31344
0.7013	Intermediate Similarity	NPC471693
0.7013	Intermediate Similarity	NPC317769
0.7013	Intermediate Similarity	NPC280704
0.7011	Intermediate Similarity	NPC247251
0.7011	Intermediate Similarity	NPC60186
0.7	Intermediate Similarity	NPC86947
0.7	Intermediate Similarity	NPC275027
0.7	Intermediate Similarity	NPC82285
0.7	Intermediate Similarity	NPC133011
0.6994	Remote Similarity	NPC314682
0.6994	Remote Similarity	NPC477837
0.6994	Remote Similarity	NPC477838
0.6989	Remote Similarity	NPC268503
0.6989	Remote Similarity	NPC42549
0.6989	Remote Similarity	NPC240841
0.6989	Remote Similarity	NPC317272
0.6989	Remote Similarity	NPC250846
0.6989	Remote Similarity	NPC256012
0.6974	Remote Similarity	NPC321133
0.6971	Remote Similarity	NPC324144
0.697	Remote Similarity	NPC136860
0.697	Remote Similarity	NPC128019
0.697	Remote Similarity	NPC476567
0.6964	Remote Similarity	NPC470935
0.6964	Remote Similarity	NPC471032
0.6954	Remote Similarity	NPC166014
0.6954	Remote Similarity	NPC226428
0.6954	Remote Similarity	NPC27410
0.6944	Remote Similarity	NPC20395
0.6941	Remote Similarity	NPC127402
0.6939	Remote Similarity	NPC173746
0.6939	Remote Similarity	NPC156840
0.6939	Remote Similarity	NPC257124
0.6939	Remote Similarity	NPC8547
0.6932	Remote Similarity	NPC306843
0.6932	Remote Similarity	NPC196447
0.6932	Remote Similarity	NPC477563
0.6932	Remote Similarity	NPC276944
0.6932	Remote Similarity	NPC238530
0.6932	Remote Similarity	NPC136508
0.6932	Remote Similarity	NPC24465
0.6932	Remote Similarity	NPC13504
0.6932	Remote Similarity	NPC253043
0.6932	Remote Similarity	NPC212794
0.6932	Remote Similarity	NPC96603
0.6932	Remote Similarity	NPC232514
0.6932	Remote Similarity	NPC78222
0.6928	Remote Similarity	NPC109083
0.6928	Remote Similarity	NPC189844
0.6928	Remote Similarity	NPC224814
0.6928	Remote Similarity	NPC14007
0.6928	Remote Similarity	NPC60962
0.6928	Remote Similarity	NPC269843
0.6923	Remote Similarity	NPC472093
0.6923	Remote Similarity	NPC203133
0.6923	Remote Similarity	NPC116907
0.6923	Remote Similarity	NPC251855

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 NPC131440 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	180
0.1-0.2	868
0.2-0.3	1591
0.3-0.4	2592
0.4-0.5	2369
0.5-0.6	1179
0.6-0.7	351
0.7-0.8	20
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
0.7468	Intermediate Similarity	NPD5718	Phase 2
0.7451	Intermediate Similarity	NPD5752	Clinical (unspecified phase)
0.7438	Intermediate Similarity	NPD3060	Approved
0.7342	Intermediate Similarity	NPD6895	Approved
0.7342	Intermediate Similarity	NPD6896	Approved
0.7308	Intermediate Similarity	NPD2674	Phase 3
0.7239	Intermediate Similarity	NPD5241	Discontinued
0.7222	Intermediate Similarity	NPD4162	Approved
0.7134	Intermediate Similarity	NPD3144	Approved
0.7134	Intermediate Similarity	NPD3145	Approved
0.7101	Intermediate Similarity	NPD4179	Approved
0.7101	Intermediate Similarity	NPD4180	Approved
0.7093	Intermediate Similarity	NPD3075	Approved
0.7078	Intermediate Similarity	NPD5311	Approved
0.7078	Intermediate Similarity	NPD5310	Approved
0.7076	Intermediate Similarity	NPD2977	Approved
0.7076	Intermediate Similarity	NPD2978	Approved
0.707	Intermediate Similarity	NPD2669	Clinical (unspecified phase)
0.7055	Intermediate Similarity	NPD4664	Clinical (unspecified phase)
0.7032	Intermediate Similarity	NPD3055	Approved
0.7032	Intermediate Similarity	NPD3053	Approved
0.7022	Intermediate Similarity	NPD5708	Clinical (unspecified phase)
0.7006	Intermediate Similarity	NPD4123	Phase 3
0.6988	Remote Similarity	NPD7124	Phase 2
0.6975	Remote Similarity	NPD6028	Clinical (unspecified phase)
0.6975	Remote Similarity	NPD6029	Clinical (unspecified phase)
0.6974	Remote Similarity	NPD2667	Approved
0.6974	Remote Similarity	NPD2668	Approved
0.6971	Remote Similarity	NPD2644	Approved
0.6939	Remote Similarity	NPD228	Approved
0.6909	Remote Similarity	NPD5177	Phase 3
0.6909	Remote Similarity	NPD4237	Approved
0.6909	Remote Similarity	NPD4236	Phase 3
0.6905	Remote Similarity	NPD1754	Clinical (unspecified phase)
0.6893	Remote Similarity	NPD4010	Discontinued
0.6879	Remote Similarity	NPD6818	Clinical (unspecified phase)
0.6852	Remote Similarity	NPD5314	Approved
0.6839	Remote Similarity	NPD2232	Approved
0.6839	Remote Similarity	NPD2233	Approved
0.6839	Remote Similarity	NPD2230	Approved
0.6836	Remote Similarity	NPD7802	Discontinued
0.6832	Remote Similarity	NPD3059	Approved
0.6832	Remote Similarity	NPD3062	Approved
0.6832	Remote Similarity	NPD3061	Approved
0.6824	Remote Similarity	NPD6662	Clinical (unspecified phase)
0.6805	Remote Similarity	NPD4584	Approved
0.6805	Remote Similarity	NPD4739	Approved
0.6802	Remote Similarity	NPD4675	Approved
0.6802	Remote Similarity	NPD4678	Approved
0.6795	Remote Similarity	NPD4379	Clinical (unspecified phase)
0.6772	Remote Similarity	NPD7905	Discontinued
0.6772	Remote Similarity	NPD6584	Phase 3
0.6766	Remote Similarity	NPD6331	Phase 2
0.6761	Remote Similarity	NPD7833	Phase 2
0.6761	Remote Similarity	NPD7832	Clinical (unspecified phase)
0.6761	Remote Similarity	NPD7831	Phase 2
0.675	Remote Similarity	NPD3027	Phase 3
0.6748	Remote Similarity	NPD2653	Approved
0.6733	Remote Similarity	NPD5283	Phase 1
0.6728	Remote Similarity	NPD2238	Phase 2
0.6726	Remote Similarity	NPD5084	Clinical (unspecified phase)
0.6708	Remote Similarity	NPD2028	Clinical (unspecified phase)
0.6705	Remote Similarity	NPD1642	Discontinued
0.6705	Remote Similarity	NPD6876	Approved
0.6705	Remote Similarity	NPD6875	Approved
0.6687	Remote Similarity	NPD5085	Clinical (unspecified phase)
0.6686	Remote Similarity	NPD3687	Approved
0.6686	Remote Similarity	NPD3686	Approved
0.6686	Remote Similarity	NPD6064	Phase 1
0.6686	Remote Similarity	NPD5773	Approved
0.6686	Remote Similarity	NPD5772	Approved
0.6686	Remote Similarity	NPD6783	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD7109	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD554	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD7110	Phase 1
0.6647	Remote Similarity	NPD824	Approved
0.6647	Remote Similarity	NPD7153	Discontinued
0.6646	Remote Similarity	NPD2922	Phase 1
0.6646	Remote Similarity	NPD9634	Clinical (unspecified phase)
0.663	Remote Similarity	NPD2489	Approved
0.663	Remote Similarity	NPD27	Approved
0.6629	Remote Similarity	NPD7945	Clinical (unspecified phase)
0.6629	Remote Similarity	NPD7298	Approved
0.6628	Remote Similarity	NPD6031	Approved
0.6628	Remote Similarity	NPD6030	Approved
0.6627	Remote Similarity	NPD2161	Phase 2
0.6627	Remote Similarity	NPD5307	Clinical (unspecified phase)
0.6606	Remote Similarity	NPD6111	Discontinued
0.6593	Remote Similarity	NPD730	Discontinued
0.6592	Remote Similarity	NPD7201	Clinical (unspecified phase)
0.6582	Remote Similarity	NPD1669	Approved
0.6582	Remote Similarity	NPD6582	Phase 2
0.6582	Remote Similarity	NPD6583	Phase 3
0.6578	Remote Similarity	NPD8054	Approved
0.6578	Remote Similarity	NPD8053	Approved
0.6573	Remote Similarity	NPD5604	Discontinued
0.6571	Remote Similarity	NPD4773	Phase 2
0.6571	Remote Similarity	NPD4772	Phase 2
0.657	Remote Similarity	NPD2236	Approved
0.6568	Remote Similarity	NPD6658	Clinical (unspecified phase)
0.6562	Remote Similarity	NPD9621	Approved
0.6562	Remote Similarity	NPD9619	Approved
0.6562	Remote Similarity	NPD9620	Approved
0.6556	Remote Similarity	NPD9379	Approved
0.6556	Remote Similarity	NPD9377	Approved
0.6554	Remote Similarity	NPD2560	Approved
0.6554	Remote Similarity	NPD2563	Approved
0.6552	Remote Similarity	NPD4005	Discontinued
0.6552	Remote Similarity	NPD7261	Clinical (unspecified phase)
0.6552	Remote Similarity	NPD4017	Approved
0.6538	Remote Similarity	NPD2898	Approved
0.6534	Remote Similarity	NPD5720	Discontinued
0.6524	Remote Similarity	NPD1558	Phase 1
0.6513	Remote Similarity	NPD2228	Approved
0.6513	Remote Similarity	NPD2234	Approved
0.6513	Remote Similarity	NPD2229	Approved
0.6512	Remote Similarity	NPD1771	Clinical (unspecified phase)
0.6503	Remote Similarity	NPD598	Approved
0.6503	Remote Similarity	NPD597	Approved
0.6503	Remote Similarity	NPD601	Approved
0.6497	Remote Similarity	NPD487	Discontinued
0.6497	Remote Similarity	NPD1671	Clinical (unspecified phase)
0.6489	Remote Similarity	NPD7090	Clinical (unspecified phase)
0.6488	Remote Similarity	NPD2029	Clinical (unspecified phase)
0.6488	Remote Similarity	NPD1375	Discontinued
0.6484	Remote Similarity	NPD2969	Approved
0.6484	Remote Similarity	NPD2970	Approved
0.6484	Remote Similarity	NPD4083	Discontinued
0.6478	Remote Similarity	NPD3676	Clinical (unspecified phase)
0.6477	Remote Similarity	NPD6873	Phase 2
0.6474	Remote Similarity	NPD5261	Clinical (unspecified phase)
0.6474	Remote Similarity	NPD3647	Clinical (unspecified phase)
0.6474	Remote Similarity	NPD4093	Discontinued
0.6467	Remote Similarity	NPD3022	Approved
0.6467	Remote Similarity	NPD3021	Approved
0.6463	Remote Similarity	NPD1136	Approved
0.6463	Remote Similarity	NPD1130	Approved
0.6463	Remote Similarity	NPD1132	Approved
0.6461	Remote Similarity	NPD6374	Clinical (unspecified phase)
0.6457	Remote Similarity	NPD6055	Clinical (unspecified phase)
0.6448	Remote Similarity	NPD7015	Phase 2
0.6448	Remote Similarity	NPD7016	Phase 3
0.6446	Remote Similarity	NPD3052	Approved
0.6446	Remote Similarity	NPD4579	Clinical (unspecified phase)
0.6446	Remote Similarity	NPD3054	Approved
0.6437	Remote Similarity	NPD3640	Phase 3
0.6437	Remote Similarity	NPD3641	Approved
0.6437	Remote Similarity	NPD2122	Discontinued
0.6437	Remote Similarity	NPD3639	Approved
0.6436	Remote Similarity	NPD3534	Clinical (unspecified phase)
0.6433	Remote Similarity	NPD2219	Phase 1
0.6429	Remote Similarity	NPD6071	Discontinued
0.6429	Remote Similarity	NPD3051	Approved
0.6425	Remote Similarity	NPD6788	Approved
0.6424	Remote Similarity	NPD3620	Phase 2
0.6424	Remote Similarity	NPD3619	Clinical (unspecified phase)
0.6416	Remote Similarity	NPD3536	Discontinued
0.6416	Remote Similarity	NPD1424	Approved
0.6415	Remote Similarity	NPD2337	Clinical (unspecified phase)
0.6402	Remote Similarity	NPD5110	Phase 2
0.6402	Remote Similarity	NPD5111	Phase 2
0.6402	Remote Similarity	NPD5109	Approved
0.64	Remote Similarity	NPD4210	Discontinued
0.6389	Remote Similarity	NPD7975	Clinical (unspecified phase)
0.6384	Remote Similarity	NPD1757	Discontinued
0.6384	Remote Similarity	NPD6385	Approved
0.6384	Remote Similarity	NPD6386	Approved
0.6384	Remote Similarity	NPD6072	Discontinued
0.6379	Remote Similarity	NPD52	Approved
0.6379	Remote Similarity	NPD7526	Approved
0.6379	Remote Similarity	NPD7527	Clinical (unspecified phase)
0.6369	Remote Similarity	NPD1753	Discontinued
0.6364	Remote Similarity	NPD3530	Approved
0.6364	Remote Similarity	NPD3532	Approved
0.6364	Remote Similarity	NPD6297	Approved
0.6364	Remote Similarity	NPD3455	Phase 2
0.6364	Remote Similarity	NPD3531	Approved
0.6358	Remote Similarity	NPD2420	Approved
0.6358	Remote Similarity	NPD1792	Phase 2
0.6358	Remote Similarity	NPD2421	Approved
0.6358	Remote Similarity	NPD1786	Approved
0.6358	Remote Similarity	NPD1785	Approved
0.6358	Remote Similarity	NPD1787	Approved
0.6353	Remote Similarity	NPD7037	Approved
0.6353	Remote Similarity	NPD1044	Clinical (unspecified phase)
0.6353	Remote Similarity	NPD2030	Discontinued
0.6349	Remote Similarity	NPD7312	Approved
0.6349	Remote Similarity	NPD7313	Approved
0.6349	Remote Similarity	NPD7310	Approved
0.6349	Remote Similarity	NPD7311	Approved
0.6347	Remote Similarity	NPD823	Approved
0.6347	Remote Similarity	NPD2492	Phase 1
0.6347	Remote Similarity	NPD817	Approved
0.6346	Remote Similarity	NPD5536	Phase 2
0.6337	Remote Similarity	NPD3692	Discontinued
0.6335	Remote Similarity	NPD7258	Clinical (unspecified phase)
0.6331	Remote Similarity	NPD1632	Clinical (unspecified phase)
0.6331	Remote Similarity	NPD6032	Approved
0.6329	Remote Similarity	NPD9381	Approved
0.6329	Remote Similarity	NPD9384	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