NPASS Compound

Structure

CID121100 OpenBabel06191715472D 24 26 0 0 0 0 0 0 0 0999 V2000 2.6228 -1.0990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1294 3.5291 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5549 2.4040 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6228 1.9010 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6228 -0.0990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5633 2.6282 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4888 1.4010 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7568 1.4010 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7568 0.4010 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4888 0.4010 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5605 2.5534 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4311 0.8262 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 1.8019 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9944 1.6525 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4339 0.9010 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9749 -0.2225 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3548 -0.0990 0.0000 Cl 0 0 0 0 0 0 0 0 0 0 0 0 -2.1238 3.3797 0.0000 Cl 0 0 0 0 0 0 0 0 0 0 0 0 -1.8650 -0.0747 0.0000 Cl 0 0 0 0 0 0 0 0 0 0 0 0 4.3548 1.9010 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.1974 -1.1974 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.9916 1.5777 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.9749 2.0245 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 5 1 0 0 0 0 2 6 1 0 0 0 0 3 22 1 0 0 0 0 4 7 1 0 0 0 0 4 8 2 0 0 0 0 5 9 2 0 0 0 0 5 10 1 0 0 0 0 6 11 2 0 0 0 0 6 13 1 0 0 0 0 7 10 2 0 0 0 0 7 20 1 0 0 0 0 8 9 1 0 0 0 0 8 23 1 0 0 0 0 9 16 1 0 0 0 0 10 17 1 0 0 0 0 11 14 1 0 0 0 0 11 18 1 0 0 0 0 12 14 2 0 0 0 0 12 15 1 0 0 0 0 12 19 1 0 0 0 0 13 15 2 0 0 0 0 13 23 1 0 0 0 0 14 22 1 0 0 0 0 15 24 1 0 0 0 0 16 21 2 0 0 0 0 16 24 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	387.97
Volume:	330.752
LogP:	5.674
LogD:	3.819
LogS:	-7.244
# Rotatable Bonds:	1
TPSA:	64.99
# H-Bond Aceptor:	5
# H-Bond Donor:	1
# Rings:	3
# Heavy Atoms:	8

MedChem Properties

QED Drug-Likeness Score:	0.529
Synthetic Accessibility Score:	3.155
Fsp3:	0.188
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.87
MDCK Permeability:	2.14149276871467e-05
Pgp-inhibitor:	0.008
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.137
20% Bioavailability (F20%):	0.001
30% Bioavailability (F30%):	0.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.029
Plasma Protein Binding (PPB):	101.33683776855469%
Volume Distribution (VD):	0.553
Pgp-substrate:	1.0650289058685303%

ADMET: Metabolism

CYP1A2-inhibitor:	0.607
CYP1A2-substrate:	0.867
CYP2C19-inhibitor:	0.726
CYP2C19-substrate:	0.311
CYP2C9-inhibitor:	0.904
CYP2C9-substrate:	0.934
CYP2D6-inhibitor:	0.003
CYP2D6-substrate:	0.398
CYP3A4-inhibitor:	0.156
CYP3A4-substrate:	0.323

ADMET: Excretion

Clearance (CL):	8.782
Half-life (T1/2):	0.179

ADMET: Toxicity

hERG Blockers:	0.006
Human Hepatotoxicity (H-HT):	0.024
Drug-inuced Liver Injury (DILI):	0.452
AMES Toxicity:	0.019
Rat Oral Acute Toxicity:	0.979
Maximum Recommended Daily Dose:	0.932
Skin Sensitization:	0.665
Carcinogencity:	0.467
Eye Corrosion:	0.005
Eye Irritation:	0.954
Respiratory Toxicity:	0.923

Download Data

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

Natural Product: NPC121100

Natural Product ID:	NPC121100
*Common Name:**	Dechlorodeploicin
IUPAC Name:	2,4,8-trichloro-9-hydroxy-3-methoxy-1,7-dimethylbenzo[b][1,4]benzodioxepin-6-one
Synonyms:	Dechlorodeploicin
Standard InCHIKey:	LSRZUHYIVQJJRO-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C16H11Cl3O5/c1-5-9-8(4-7(20)10(5)17)23-13-6(2)11(18)14(22-3)12(19)15(13)24-16(9)21/h4,20H,1-3H3
SMILES:	COc1c(Cl)c2OC(=O)c3c(Oc2c(c1Cl)C)cc(c(c3C)Cl)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1079485
PubChem CID:	46879135
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0001645] Depsides and depsidones

*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
NPO25148	Helichrysum italicum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11678669]
NPO13590	Diploicia canescens	Species	Caliciaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19919064]
NPO25148	Helichrysum italicum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24094434]
NPO25148	Helichrysum italicum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO25148	Helichrysum italicum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO6208	Trichogoniopsis morii	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13590	Diploicia canescens	Species	Caliciaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8523	Haematoxylon campechianum	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO5477	Mycosphaerella laricina	Species	Mycosphaerellaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25148	Helichrysum italicum	Species	Asteraceae	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
IC50	2

Activity Type	# Activity
Cell Line	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT319	Cell Line	B16	Mus musculus	IC50	=	1700.0	nM	PMID[569115]
NPT941	Cell Line	HaCaT	Homo sapiens	IC50	=	4300.0	nM	PMID[569115]

☑ 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 NPC121100 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	507
0.1-0.2	2647
0.2-0.3	7762
0.3-0.4	12100
0.4-0.5	4115
0.5-0.6	6184
0.6-0.7	7428
0.7-0.8	1893
0.8-0.85	29
0.85-0.9	11
0.9-0.95	6
0.95-1	15

Similarity Score	Similarity Level	Natural Product ID
0.9942	High Similarity	NPC471810
0.9942	High Similarity	NPC471806
0.9884	High Similarity	NPC471805
0.9884	High Similarity	NPC471813
0.9828	High Similarity	NPC471807
0.9713	High Similarity	NPC471803
0.9713	High Similarity	NPC471812
0.9713	High Similarity	NPC471804
0.9657	High Similarity	NPC39409
0.9653	High Similarity	NPC195675
0.9598	High Similarity	NPC471809
0.9598	High Similarity	NPC471811
0.954	High Similarity	NPC471814
0.954	High Similarity	NPC471808
0.9477	High Similarity	NPC108278
0.9368	High Similarity	NPC471801
0.9364	High Similarity	NPC175804
0.931	High Similarity	NPC471802
0.9011	High Similarity	NPC220369
0.8962	High Similarity	NPC214901
0.8771	High Similarity	NPC28160
0.877	High Similarity	NPC154720
0.8564	High Similarity	NPC198163
0.8547	High Similarity	NPC188618
0.85	High Similarity	NPC470422
0.8407	Intermediate Similarity	NPC45072
0.8368	Intermediate Similarity	NPC193676
0.8333	Intermediate Similarity	NPC471800
0.8295	Intermediate Similarity	NPC238381
0.8111	Intermediate Similarity	NPC300984
0.8111	Intermediate Similarity	NPC156082
0.8101	Intermediate Similarity	NPC303565
0.8095	Intermediate Similarity	NPC474499
0.8077	Intermediate Similarity	NPC472032
0.8066	Intermediate Similarity	NPC267153
0.8066	Intermediate Similarity	NPC112981
0.8056	Intermediate Similarity	NPC93739
0.8045	Intermediate Similarity	NPC200594
0.8022	Intermediate Similarity	NPC20216
0.8011	Intermediate Similarity	NPC284007
0.801	Intermediate Similarity	NPC470099
0.7989	Intermediate Similarity	NPC83763
0.7989	Intermediate Similarity	NPC168616
0.7978	Intermediate Similarity	NPC292788
0.7978	Intermediate Similarity	NPC272485
0.7978	Intermediate Similarity	NPC54928
0.7967	Intermediate Similarity	NPC8070
0.7956	Intermediate Similarity	NPC474096
0.7946	Intermediate Similarity	NPC474857
0.7935	Intermediate Similarity	NPC26568
0.7917	Intermediate Similarity	NPC470100
0.7912	Intermediate Similarity	NPC474350
0.791	Intermediate Similarity	NPC289968
0.7901	Intermediate Similarity	NPC298401
0.7892	Intermediate Similarity	NPC239440
0.7892	Intermediate Similarity	NPC20543
0.7892	Intermediate Similarity	NPC246716
0.7892	Intermediate Similarity	NPC107283
0.7892	Intermediate Similarity	NPC10576
0.7892	Intermediate Similarity	NPC1827
0.7892	Intermediate Similarity	NPC17219
0.7892	Intermediate Similarity	NPC277865
0.7869	Intermediate Similarity	NPC173352
0.7869	Intermediate Similarity	NPC58653
0.7861	Intermediate Similarity	NPC477568
0.7861	Intermediate Similarity	NPC264922
0.7857	Intermediate Similarity	NPC473696
0.7835	Intermediate Similarity	NPC221185
0.7826	Intermediate Similarity	NPC474061
0.7826	Intermediate Similarity	NPC28669
0.7826	Intermediate Similarity	NPC29160
0.7821	Intermediate Similarity	NPC20541
0.7814	Intermediate Similarity	NPC470081
0.7814	Intermediate Similarity	NPC234004
0.7807	Intermediate Similarity	NPC181523
0.7802	Intermediate Similarity	NPC472405
0.7801	Intermediate Similarity	NPC99937
0.7796	Intermediate Similarity	NPC470562
0.7796	Intermediate Similarity	NPC470565
0.7795	Intermediate Similarity	NPC247104
0.7784	Intermediate Similarity	NPC234331
0.7778	Intermediate Similarity	NPC472456
0.7766	Intermediate Similarity	NPC139350
0.7766	Intermediate Similarity	NPC289147
0.776	Intermediate Similarity	NPC8300
0.7759	Intermediate Similarity	NPC95123
0.7759	Intermediate Similarity	NPC66404
0.7755	Intermediate Similarity	NPC48822
0.7754	Intermediate Similarity	NPC470560
0.7753	Intermediate Similarity	NPC204350
0.7746	Intermediate Similarity	NPC105648
0.7742	Intermediate Similarity	NPC49487
0.7742	Intermediate Similarity	NPC165979
0.7742	Intermediate Similarity	NPC99613
0.7742	Intermediate Similarity	NPC163130
0.774	Intermediate Similarity	NPC328119
0.7735	Intermediate Similarity	NPC300727
0.7735	Intermediate Similarity	NPC217677
0.7735	Intermediate Similarity	NPC241904
0.7735	Intermediate Similarity	NPC472404
0.7735	Intermediate Similarity	NPC165977
0.773	Intermediate Similarity	NPC472452
0.7714	Intermediate Similarity	NPC134621
0.7701	Intermediate Similarity	NPC124470
0.7701	Intermediate Similarity	NPC109827
0.7697	Intermediate Similarity	NPC306821
0.7696	Intermediate Similarity	NPC151292
0.7692	Intermediate Similarity	NPC476242
0.7688	Intermediate Similarity	NPC220106
0.768	Intermediate Similarity	NPC313386
0.768	Intermediate Similarity	NPC316091
0.768	Intermediate Similarity	NPC227062
0.768	Intermediate Similarity	NPC274730
0.768	Intermediate Similarity	NPC136411
0.7676	Intermediate Similarity	NPC85057
0.7676	Intermediate Similarity	NPC130920
0.7676	Intermediate Similarity	NPC68850
0.767	Intermediate Similarity	NPC237208
0.7668	Intermediate Similarity	NPC191606
0.766	Intermediate Similarity	NPC158226
0.7654	Intermediate Similarity	NPC208043
0.7654	Intermediate Similarity	NPC308451
0.7654	Intermediate Similarity	NPC226973
0.7654	Intermediate Similarity	NPC117579
0.765	Intermediate Similarity	NPC474287
0.765	Intermediate Similarity	NPC475886
0.765	Intermediate Similarity	NPC14353
0.765	Intermediate Similarity	NPC56085
0.765	Intermediate Similarity	NPC228785
0.7647	Intermediate Similarity	NPC148480
0.7644	Intermediate Similarity	NPC113446
0.7644	Intermediate Similarity	NPC329161
0.7644	Intermediate Similarity	NPC306240
0.7644	Intermediate Similarity	NPC470091
0.7644	Intermediate Similarity	NPC240887
0.7637	Intermediate Similarity	NPC108456
0.7627	Intermediate Similarity	NPC62536
0.7627	Intermediate Similarity	NPC33265
0.7627	Intermediate Similarity	NPC12200
0.7626	Intermediate Similarity	NPC313541
0.7614	Intermediate Similarity	NPC472917
0.7614	Intermediate Similarity	NPC29577
0.7611	Intermediate Similarity	NPC222830
0.7611	Intermediate Similarity	NPC57030
0.7611	Intermediate Similarity	NPC187498
0.7611	Intermediate Similarity	NPC256283
0.7611	Intermediate Similarity	NPC301123
0.7611	Intermediate Similarity	NPC212678
0.7611	Intermediate Similarity	NPC239128
0.7611	Intermediate Similarity	NPC25270
0.7611	Intermediate Similarity	NPC293183
0.7611	Intermediate Similarity	NPC156222
0.7611	Intermediate Similarity	NPC162313
0.7611	Intermediate Similarity	NPC120163
0.7611	Intermediate Similarity	NPC131624
0.7611	Intermediate Similarity	NPC83508
0.7611	Intermediate Similarity	NPC71334
0.7611	Intermediate Similarity	NPC198826
0.7611	Intermediate Similarity	NPC301323
0.7611	Intermediate Similarity	NPC188203
0.7611	Intermediate Similarity	NPC100887
0.7611	Intermediate Similarity	NPC241498
0.7611	Intermediate Similarity	NPC142540
0.7611	Intermediate Similarity	NPC275836
0.7611	Intermediate Similarity	NPC275722
0.7609	Intermediate Similarity	NPC474186
0.7609	Intermediate Similarity	NPC474351
0.7609	Intermediate Similarity	NPC66288
0.7609	Intermediate Similarity	NPC475883
0.7609	Intermediate Similarity	NPC474187
0.7609	Intermediate Similarity	NPC40491
0.7609	Intermediate Similarity	NPC278052
0.7609	Intermediate Similarity	NPC61010
0.76	Intermediate Similarity	NPC200207
0.76	Intermediate Similarity	NPC108744
0.7598	Intermediate Similarity	NPC179183
0.7596	Intermediate Similarity	NPC267627
0.7596	Intermediate Similarity	NPC40702
0.7596	Intermediate Similarity	NPC100123
0.7596	Intermediate Similarity	NPC37502
0.7596	Intermediate Similarity	NPC45846
0.7584	Intermediate Similarity	NPC120464
0.7584	Intermediate Similarity	NPC195202
0.7581	Intermediate Similarity	NPC234053
0.7577	Intermediate Similarity	NPC470103
0.7571	Intermediate Similarity	NPC267509
0.7571	Intermediate Similarity	NPC138978
0.7569	Intermediate Similarity	NPC22519
0.7569	Intermediate Similarity	NPC250822
0.7569	Intermediate Similarity	NPC472915
0.7569	Intermediate Similarity	NPC274327
0.7569	Intermediate Similarity	NPC69394
0.7569	Intermediate Similarity	NPC47781
0.7569	Intermediate Similarity	NPC183878
0.7569	Intermediate Similarity	NPC276409
0.7569	Intermediate Similarity	NPC475895
0.7569	Intermediate Similarity	NPC86485
0.7569	Intermediate Similarity	NPC255350
0.7569	Intermediate Similarity	NPC280937
0.7569	Intermediate Similarity	NPC231018

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 NPC121100 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	448
0.1-0.2	1251
0.2-0.3	2422
0.3-0.4	2640
0.4-0.5	1514
0.5-0.6	666
0.6-0.7	187
0.7-0.8	22
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
0.767	Intermediate Similarity	NPD1940	Clinical (unspecified phase)
0.7584	Intermediate Similarity	NPD2370	Clinical (unspecified phase)
0.7581	Intermediate Similarity	NPD2403	Approved
0.7569	Intermediate Similarity	NPD2801	Approved
0.7418	Intermediate Similarity	NPD1934	Approved
0.738	Intermediate Similarity	NPD6232	Discontinued
0.7377	Intermediate Similarity	NPD1465	Phase 2
0.7371	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7368	Intermediate Similarity	NPD5844	Phase 1
0.7337	Intermediate Similarity	NPD3817	Phase 2
0.7263	Intermediate Similarity	NPD1511	Approved
0.7263	Intermediate Similarity	NPD7473	Discontinued
0.7204	Intermediate Similarity	NPD3882	Suspended
0.7189	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7182	Intermediate Similarity	NPD1512	Approved
0.7128	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7112	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7097	Intermediate Similarity	NPD7819	Suspended
0.7031	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7031	Intermediate Similarity	NPD6166	Phase 2
0.7031	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.701	Intermediate Similarity	NPD7054	Approved
0.7	Intermediate Similarity	NPD5494	Approved
0.6989	Remote Similarity	NPD958	Approved
0.6978	Remote Similarity	NPD6799	Approved
0.6974	Remote Similarity	NPD7074	Phase 3
0.6974	Remote Similarity	NPD7472	Approved
0.6959	Remote Similarity	NPD3818	Discontinued
0.694	Remote Similarity	NPD2533	Approved
0.694	Remote Similarity	NPD2532	Approved
0.694	Remote Similarity	NPD4378	Clinical (unspecified phase)
0.694	Remote Similarity	NPD2534	Approved
0.6932	Remote Similarity	NPD1184	Approved
0.6932	Remote Similarity	NPD447	Suspended
0.6919	Remote Similarity	NPD957	Approved
0.6906	Remote Similarity	NPD3750	Approved
0.6895	Remote Similarity	NPD7075	Discontinued
0.6895	Remote Similarity	NPD3749	Approved
0.6875	Remote Similarity	NPD6959	Discontinued
0.6872	Remote Similarity	NPD2935	Discontinued
0.6869	Remote Similarity	NPD7808	Phase 3
0.6859	Remote Similarity	NPD919	Approved
0.6853	Remote Similarity	NPD6797	Phase 2
0.6845	Remote Similarity	NPD6599	Discontinued
0.6833	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.6833	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6825	Remote Similarity	NPD7096	Clinical (unspecified phase)
0.6818	Remote Similarity	NPD7251	Discontinued
0.6796	Remote Similarity	NPD1549	Phase 2
0.6789	Remote Similarity	NPD5402	Approved
0.678	Remote Similarity	NPD1240	Approved
0.6778	Remote Similarity	NPD1551	Phase 2
0.6776	Remote Similarity	NPD2354	Approved
0.6772	Remote Similarity	NPD6801	Discontinued
0.6768	Remote Similarity	NPD7993	Clinical (unspecified phase)
0.6742	Remote Similarity	NPD230	Phase 1
0.6722	Remote Similarity	NPD1510	Phase 2
0.672	Remote Similarity	NPD7411	Suspended
0.6719	Remote Similarity	NPD4381	Clinical (unspecified phase)
0.6704	Remote Similarity	NPD1607	Approved
0.6702	Remote Similarity	NPD3226	Approved
0.6701	Remote Similarity	NPD1247	Approved
0.6701	Remote Similarity	NPD7199	Phase 2
0.6699	Remote Similarity	NPD4363	Phase 3
0.6699	Remote Similarity	NPD4360	Phase 2
0.6667	Remote Similarity	NPD8397	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD4380	Phase 2
0.6667	Remote Similarity	NPD7768	Phase 2
0.6667	Remote Similarity	NPD2800	Approved
0.6667	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6648	Remote Similarity	NPD2353	Approved
0.6648	Remote Similarity	NPD2355	Clinical (unspecified phase)
0.6633	Remote Similarity	NPD7184	Clinical (unspecified phase)
0.6633	Remote Similarity	NPD3926	Phase 2
0.663	Remote Similarity	NPD3748	Approved
0.6618	Remote Similarity	NPD6312	Discontinued
0.6615	Remote Similarity	NPD8443	Clinical (unspecified phase)
0.6599	Remote Similarity	NPD7852	Clinical (unspecified phase)
0.6598	Remote Similarity	NPD6234	Discontinued
0.6597	Remote Similarity	NPD37	Approved
0.6596	Remote Similarity	NPD920	Approved
0.6596	Remote Similarity	NPD6980	Clinical (unspecified phase)
0.6595	Remote Similarity	NPD3887	Approved
0.6593	Remote Similarity	NPD2796	Approved
0.6591	Remote Similarity	NPD454	Approved
0.6587	Remote Similarity	NPD4361	Phase 2
0.6587	Remote Similarity	NPD4362	Clinical (unspecified phase)
0.658	Remote Similarity	NPD4966	Approved
0.658	Remote Similarity	NPD4967	Phase 2
0.658	Remote Similarity	NPD4965	Approved
0.6578	Remote Similarity	NPD7410	Clinical (unspecified phase)
0.6578	Remote Similarity	NPD1578	Phase 2
0.6576	Remote Similarity	NPD1243	Approved
0.6571	Remote Similarity	NPD1203	Approved
0.6556	Remote Similarity	NPD1933	Approved
0.6541	Remote Similarity	NPD4628	Phase 3
0.6541	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.6538	Remote Similarity	NPD2799	Discontinued
0.6538	Remote Similarity	NPD651	Clinical (unspecified phase)
0.6524	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6508	Remote Similarity	NPD5403	Approved
0.65	Remote Similarity	NPD7804	Clinical (unspecified phase)
0.65	Remote Similarity	NPD943	Approved
0.6497	Remote Similarity	NPD5710	Approved
0.6497	Remote Similarity	NPD5711	Approved
0.6492	Remote Similarity	NPD4972	Discontinued
0.6489	Remote Similarity	NPD5401	Approved
0.6485	Remote Similarity	NPD6559	Discontinued
0.6474	Remote Similarity	NPD1653	Approved
0.6467	Remote Similarity	NPD2346	Discontinued
0.6464	Remote Similarity	NPD1899	Clinical (unspecified phase)
0.645	Remote Similarity	NPD3751	Discontinued
0.6442	Remote Similarity	NPD7879	Clinical (unspecified phase)
0.6432	Remote Similarity	NPD4534	Discontinued
0.6418	Remote Similarity	NPD7286	Phase 2
0.6404	Remote Similarity	NPD1530	Clinical (unspecified phase)
0.6404	Remote Similarity	NPD3303	Discontinued
0.6402	Remote Similarity	NPD642	Clinical (unspecified phase)
0.64	Remote Similarity	NPD9717	Approved
0.6398	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6385	Remote Similarity	NPD7501	Clinical (unspecified phase)
0.6383	Remote Similarity	NPD643	Clinical (unspecified phase)
0.6382	Remote Similarity	NPD5242	Approved
0.6369	Remote Similarity	NPD1529	Clinical (unspecified phase)
0.6369	Remote Similarity	NPD6832	Phase 2
0.6368	Remote Similarity	NPD7228	Approved
0.6364	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6359	Remote Similarity	NPD8055	Clinical (unspecified phase)
0.6359	Remote Similarity	NPD1509	Clinical (unspecified phase)
0.6359	Remote Similarity	NPD2379	Clinical (unspecified phase)
0.6359	Remote Similarity	NPD8438	Clinical (unspecified phase)
0.6355	Remote Similarity	NPD5953	Discontinued
0.6344	Remote Similarity	NPD5958	Discontinued
0.6343	Remote Similarity	NPD422	Phase 1
0.6332	Remote Similarity	NPD3787	Discontinued
0.6324	Remote Similarity	NPD6099	Approved
0.6324	Remote Similarity	NPD1501	Clinical (unspecified phase)
0.6324	Remote Similarity	NPD6100	Approved
0.6319	Remote Similarity	NPD1613	Approved
0.6319	Remote Similarity	NPD1612	Clinical (unspecified phase)
0.6307	Remote Similarity	NPD1608	Approved
0.6298	Remote Similarity	NPD411	Approved
0.629	Remote Similarity	NPD2344	Approved
0.628	Remote Similarity	NPD1163	Approved
0.6276	Remote Similarity	NPD5353	Approved
0.6276	Remote Similarity	NPD4288	Approved
0.6269	Remote Similarity	NPD5822	Clinical (unspecified phase)
0.6263	Remote Similarity	NPD7390	Discontinued
0.625	Remote Similarity	NPD6651	Approved
0.625	Remote Similarity	NPD7229	Phase 3
0.6244	Remote Similarity	NPD7782	Clinical (unspecified phase)
0.6244	Remote Similarity	NPD7783	Phase 2
0.6243	Remote Similarity	NPD6190	Approved
0.6243	Remote Similarity	NPD3027	Phase 3
0.6216	Remote Similarity	NPD4536	Approved
0.6216	Remote Similarity	NPD4537	Clinical (unspecified phase)
0.6216	Remote Similarity	NPD4538	Approved
0.6215	Remote Similarity	NPD9269	Phase 2
0.6214	Remote Similarity	NPD7549	Discontinued
0.6209	Remote Similarity	NPD3268	Approved
0.6209	Remote Similarity	NPD2313	Discontinued
0.6209	Remote Similarity	NPD1699	Clinical (unspecified phase)
0.6205	Remote Similarity	NPD6385	Approved
0.6205	Remote Similarity	NPD6386	Approved
0.6202	Remote Similarity	NPD6784	Approved
0.6202	Remote Similarity	NPD6785	Approved
0.6201	Remote Similarity	NPD2797	Approved
0.619	Remote Similarity	NPD4287	Approved
0.6184	Remote Similarity	NPD8312	Approved
0.6184	Remote Similarity	NPD8313	Approved
0.6183	Remote Similarity	NPD4308	Phase 3
0.6172	Remote Similarity	NPD8434	Phase 2
0.6171	Remote Similarity	NPD9268	Approved
0.6165	Remote Similarity	NPD7685	Pre-registration
0.6158	Remote Similarity	NPD2309	Approved
0.6154	Remote Similarity	NPD8151	Discontinued
0.615	Remote Similarity	NPD3365	Discontinued
0.6147	Remote Similarity	NPD7435	Discontinued
0.6146	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6145	Remote Similarity	NPD3225	Approved
0.6141	Remote Similarity	NPD4060	Phase 1
0.6136	Remote Similarity	NPD17	Approved
0.6135	Remote Similarity	NPD4419	Clinical (unspecified phase)
0.6133	Remote Similarity	NPD9494	Approved
0.6126	Remote Similarity	NPD5058	Phase 3
0.6124	Remote Similarity	NPD1481	Phase 2
0.612	Remote Similarity	NPD3764	Approved
0.612	Remote Similarity	NPD1296	Phase 2
0.6119	Remote Similarity	NPD8127	Discontinued
0.6103	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6102	Remote Similarity	NPD915	Approved
0.6096	Remote Similarity	NPD7033	Discontinued
0.6096	Remote Similarity	NPD5588	Approved
0.6096	Remote Similarity	NPD5960	Phase 3
0.6095	Remote Similarity	NPD8150	Discontinued
0.6087	Remote Similarity	NPD7240	Approved
0.6087	Remote Similarity	NPD7038	Approved
0.6087	Remote Similarity	NPD7039	Approved
0.6087	Remote Similarity	NPD6233	Phase 2
0.6083	Remote Similarity	NPD6778	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