NPASS Compound

Structure

NPC472157 OpenBabel07101718202D 25 29 0 0 0 0 0 0 0 0999 V2000 3.1631 0.9757 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4311 -2.0243 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1631 -0.0243 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2971 -1.5243 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2971 1.4757 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5651 -1.5243 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6744 -1.2313 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5405 -0.7313 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8084 2.2687 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0576 1.7687 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2971 -0.5243 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8084 -0.7313 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5405 0.2687 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6744 1.7687 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4311 0.9757 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5651 -0.5243 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4311 -0.0243 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6744 0.7687 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8084 0.2687 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0576 0.7687 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0576 -1.2313 0.0000 Cl 0 0 0 0 0 0 0 0 0 0 0 0 -3.4065 0.7687 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5405 2.2687 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.6945 1.2029 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 3 2 0 0 0 0 1 5 1 0 0 0 0 2 4 2 0 0 0 0 2 6 1 0 0 0 0 3 11 1 0 0 0 0 4 11 1 0 0 0 0 5 15 2 0 0 0 0 6 16 2 0 0 0 0 7 8 2 0 0 0 0 7 12 1 0 0 0 0 8 13 1 0 0 0 0 9 10 1 0 0 0 0 9 14 1 0 0 0 0 10 20 1 0 0 0 0 11 17 2 0 0 0 0 12 19 2 0 0 0 0 12 21 1 0 0 0 0 13 18 2 0 0 0 0 13 22 1 0 0 0 0 14 18 1 0 0 0 0 14 23 2 0 0 0 0 15 17 1 0 0 0 0 15 24 1 0 0 0 0 16 17 1 0 0 0 0 16 25 1 0 0 0 0 18 19 1 0 0 0 0 19 20 1 0 0 0 0 20 24 1 0 0 0 0 20 25 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	352.05
Volume:	338.338
LogP:	4.727
LogD:	3.458
LogS:	-4.839
# Rotatable Bonds:	0
TPSA:	55.76
# H-Bond Aceptor:	4
# H-Bond Donor:	1
# Rings:	5
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.631
Synthetic Accessibility Score:	3.327
Fsp3:	0.15
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:	-4.992
MDCK Permeability:	1.7932137780007906e-05
Pgp-inhibitor:	0.115
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.003
20% Bioavailability (F20%):	0.003
30% Bioavailability (F30%):	0.008

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.21
Plasma Protein Binding (PPB):	98.40184783935547%
Volume Distribution (VD):	0.583
Pgp-substrate:	0.8572680950164795%

ADMET: Metabolism

CYP1A2-inhibitor:	0.937
CYP1A2-substrate:	0.312
CYP2C19-inhibitor:	0.939
CYP2C19-substrate:	0.082
CYP2C9-inhibitor:	0.924
CYP2C9-substrate:	0.937
CYP2D6-inhibitor:	0.753
CYP2D6-substrate:	0.417
CYP3A4-inhibitor:	0.74
CYP3A4-substrate:	0.339

ADMET: Excretion

Clearance (CL):	5.77
Half-life (T1/2):	0.444

ADMET: Toxicity

hERG Blockers:	0.027
Human Hepatotoxicity (H-HT):	0.4
Drug-inuced Liver Injury (DILI):	0.952
AMES Toxicity:	0.932
Rat Oral Acute Toxicity:	0.77
Maximum Recommended Daily Dose:	0.585
Skin Sensitization:	0.64
Carcinogencity:	0.93
Eye Corrosion:	0.003
Eye Irritation:	0.742
Respiratory Toxicity:	0.898

Download Data

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

Natural Product: NPC472157

Natural Product ID:	NPC472157
*Common Name:**	YWUWMXDEUDNGHC-UHFFFAOYSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	YWUWMXDEUDNGHC-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C20H13ClO4/c21-12-7-8-13(22)18-14(23)9-10-20(19(12)18)24-15-5-1-3-11-4-2-6-16(25-20)17(11)15/h1-8,22H,9-10H2
SMILES:	Clc1ccc(c2c1C1(CCC2=O)Oc2cccc3c2c(O1)ccc3)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3342637
PubChem CID:	n.a.
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0000048] Tetralins

*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
NPO33512	berkleasmium sp.	Species	n.a.	Eukaryota	n.a.	n.a.	n.a.	PMID[25237727]

☑ 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	6
MIC	6
Others	1

Activity Type	# Activity
Cell Line	2
NON-MOLECULAR	3
Organism	8

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT81	Cell Line	A549	Homo sapiens	IC50	>	10000.0	nM	PMID[497404]
NPT179	Cell Line	A2780	Homo sapiens	IC50	>	10000.0	nM	PMID[497404]
NPT79	Organism	Bacillus subtilis	Bacillus subtilis	MIC	>	250.0	ug.mL-1	PMID[497404]
NPT141	Organism	Agrobacterium tumefaciens	Agrobacterium tumefaciens	MIC	>	250.0	ug.mL-1	PMID[497404]
NPT1477	Organism	Staphylococcus haemolyticus	Staphylococcus haemolyticus	MIC	>	250.0	ug.mL-1	PMID[497404]
NPT331	Organism	Ralstonia solanacearum	Ralstonia solanacearum	MIC	>	250.0	ug.mL-1	PMID[497404]
NPT2921	Organism	Pseudomonas	Pseudomonas	MIC	>	250.0	ug.mL-1	PMID[497404]
NPT4150	Organism	Xanthomonas vesicatoria	Xanthomonas vesicatoria	MIC	>	250.0	ug.mL-1	PMID[497404]
NPT826	Organism	Magnaporthe oryzae	Magnaporthe oryzae	IC50	>	200.0	ug.mL-1	PMID[497404]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	>	10000.0	nM	PMID[497404]
NPT6274	Organism	Aedes albopictus	Aedes albopictus	LC50	=	227300.0	nM	PMID[497405]

☑ 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 NPC472157 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	472
0.1-0.2	2263
0.2-0.3	6009
0.3-0.4	13185
0.4-0.5	4083
0.5-0.6	6710
0.6-0.7	7954
0.7-0.8	2012
0.8-0.85	5
0.85-0.9	3
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9013	High Similarity	NPC306816
0.8896	High Similarity	NPC301949
0.8831	High Similarity	NPC47152
0.8471	Intermediate Similarity	NPC473951
0.8232	Intermediate Similarity	NPC57141
0.8204	Intermediate Similarity	NPC73148
0.805	Intermediate Similarity	NPC133585
0.805	Intermediate Similarity	NPC197461
0.8038	Intermediate Similarity	NPC473499
0.8012	Intermediate Similarity	NPC97662
0.7888	Intermediate Similarity	NPC257404
0.7829	Intermediate Similarity	NPC474857
0.7784	Intermediate Similarity	NPC85368
0.7771	Intermediate Similarity	NPC277865
0.7765	Intermediate Similarity	NPC151292
0.7744	Intermediate Similarity	NPC206579
0.7744	Intermediate Similarity	NPC11800
0.774	Intermediate Similarity	NPC264922
0.7735	Intermediate Similarity	NPC191606
0.7719	Intermediate Similarity	NPC292863
0.7719	Intermediate Similarity	NPC184326
0.7697	Intermediate Similarity	NPC45072
0.7692	Intermediate Similarity	NPC254351
0.7692	Intermediate Similarity	NPC141549
0.7684	Intermediate Similarity	NPC470422
0.7674	Intermediate Similarity	NPC137232
0.7674	Intermediate Similarity	NPC18380
0.767	Intermediate Similarity	NPC472160
0.767	Intermediate Similarity	NPC472159
0.7661	Intermediate Similarity	NPC195167
0.7661	Intermediate Similarity	NPC183402
0.7657	Intermediate Similarity	NPC472032
0.7651	Intermediate Similarity	NPC35150
0.7651	Intermediate Similarity	NPC106328
0.765	Intermediate Similarity	NPC313386
0.765	Intermediate Similarity	NPC316091
0.7644	Intermediate Similarity	NPC11608
0.7644	Intermediate Similarity	NPC297404
0.764	Intermediate Similarity	NPC18457
0.7636	Intermediate Similarity	NPC211565
0.7628	Intermediate Similarity	NPC278787
0.7628	Intermediate Similarity	NPC7569
0.7619	Intermediate Similarity	NPC39819
0.7614	Intermediate Similarity	NPC137460
0.7614	Intermediate Similarity	NPC472152
0.7611	Intermediate Similarity	NPC153578
0.7611	Intermediate Similarity	NPC306240
0.7611	Intermediate Similarity	NPC277710
0.7611	Intermediate Similarity	NPC114257
0.7611	Intermediate Similarity	NPC299149
0.7611	Intermediate Similarity	NPC471801
0.7607	Intermediate Similarity	NPC69755
0.7605	Intermediate Similarity	NPC70764
0.7595	Intermediate Similarity	NPC138940
0.759	Intermediate Similarity	NPC71055
0.7586	Intermediate Similarity	NPC290160
0.7584	Intermediate Similarity	NPC59491
0.7584	Intermediate Similarity	NPC24748
0.7584	Intermediate Similarity	NPC203751
0.7574	Intermediate Similarity	NPC281272
0.7561	Intermediate Similarity	NPC310340
0.756	Intermediate Similarity	NPC325983
0.756	Intermediate Similarity	NPC470107
0.756	Intermediate Similarity	NPC295036
0.756	Intermediate Similarity	NPC227122
0.7558	Intermediate Similarity	NPC193749
0.7558	Intermediate Similarity	NPC18699
0.7558	Intermediate Similarity	NPC177650
0.7558	Intermediate Similarity	NPC55443
0.7557	Intermediate Similarity	NPC103633
0.7546	Intermediate Similarity	NPC275734
0.7546	Intermediate Similarity	NPC145673
0.7544	Intermediate Similarity	NPC137100
0.7543	Intermediate Similarity	NPC68850
0.7543	Intermediate Similarity	NPC477834
0.7542	Intermediate Similarity	NPC472158
0.753	Intermediate Similarity	NPC60389
0.7529	Intermediate Similarity	NPC216752
0.7529	Intermediate Similarity	NPC178964
0.7529	Intermediate Similarity	NPC278329
0.7529	Intermediate Similarity	NPC185103
0.7529	Intermediate Similarity	NPC95842
0.7529	Intermediate Similarity	NPC101116
0.7529	Intermediate Similarity	NPC212099
0.7529	Intermediate Similarity	NPC146837
0.7529	Intermediate Similarity	NPC280530
0.7528	Intermediate Similarity	NPC188618
0.7515	Intermediate Similarity	NPC138299
0.7515	Intermediate Similarity	NPC115324
0.7515	Intermediate Similarity	NPC111112
0.7515	Intermediate Similarity	NPC193976
0.7515	Intermediate Similarity	NPC222713
0.7515	Intermediate Similarity	NPC67322
0.7515	Intermediate Similarity	NPC23668
0.7514	Intermediate Similarity	NPC186325
0.7514	Intermediate Similarity	NPC222455
0.7514	Intermediate Similarity	NPC312993
0.75	Intermediate Similarity	NPC101991
0.75	Intermediate Similarity	NPC289876
0.75	Intermediate Similarity	NPC177742
0.75	Intermediate Similarity	NPC102053
0.7486	Intermediate Similarity	NPC231254
0.7485	Intermediate Similarity	NPC182555
0.7485	Intermediate Similarity	NPC201227
0.7485	Intermediate Similarity	NPC12305
0.7485	Intermediate Similarity	NPC300668
0.7485	Intermediate Similarity	NPC134171
0.7485	Intermediate Similarity	NPC55662
0.7485	Intermediate Similarity	NPC66441
0.7485	Intermediate Similarity	NPC166054
0.7485	Intermediate Similarity	NPC99199
0.7485	Intermediate Similarity	NPC258474
0.7472	Intermediate Similarity	NPC474004
0.7472	Intermediate Similarity	NPC470565
0.7471	Intermediate Similarity	NPC273467
0.7471	Intermediate Similarity	NPC207624
0.7471	Intermediate Similarity	NPC189552
0.7471	Intermediate Similarity	NPC474843
0.7471	Intermediate Similarity	NPC473967
0.7471	Intermediate Similarity	NPC472261
0.7471	Intermediate Similarity	NPC142308
0.747	Intermediate Similarity	NPC32470
0.747	Intermediate Similarity	NPC131766
0.7468	Intermediate Similarity	NPC137264
0.7468	Intermediate Similarity	NPC193805
0.7455	Intermediate Similarity	NPC169479
0.7455	Intermediate Similarity	NPC159855
0.7446	Intermediate Similarity	NPC87583
0.7444	Intermediate Similarity	NPC470667
0.7444	Intermediate Similarity	NPC3718
0.7443	Intermediate Similarity	NPC474591
0.7443	Intermediate Similarity	NPC178281
0.7442	Intermediate Similarity	NPC32867
0.7442	Intermediate Similarity	NPC469507
0.7442	Intermediate Similarity	NPC69531
0.7442	Intermediate Similarity	NPC13879
0.7442	Intermediate Similarity	NPC198489
0.7442	Intermediate Similarity	NPC61112
0.7442	Intermediate Similarity	NPC309648
0.7429	Intermediate Similarity	NPC477239
0.7429	Intermediate Similarity	NPC15374
0.7429	Intermediate Similarity	NPC3448
0.7427	Intermediate Similarity	NPC303485
0.7427	Intermediate Similarity	NPC72425
0.7427	Intermediate Similarity	NPC329844
0.7427	Intermediate Similarity	NPC290830
0.7427	Intermediate Similarity	NPC71061
0.7427	Intermediate Similarity	NPC92153
0.7427	Intermediate Similarity	NPC194593
0.7427	Intermediate Similarity	NPC235333
0.7427	Intermediate Similarity	NPC299761
0.7427	Intermediate Similarity	NPC230439
0.7427	Intermediate Similarity	NPC135522
0.7427	Intermediate Similarity	NPC279281
0.7425	Intermediate Similarity	NPC267509
0.7418	Intermediate Similarity	NPC58538
0.7418	Intermediate Similarity	NPC121888
0.7416	Intermediate Similarity	NPC300307
0.7414	Intermediate Similarity	NPC328093
0.7412	Intermediate Similarity	NPC106372
0.7412	Intermediate Similarity	NPC149085
0.7412	Intermediate Similarity	NPC58668
0.741	Intermediate Similarity	NPC113770
0.7407	Intermediate Similarity	NPC477534
0.7407	Intermediate Similarity	NPC313541
0.7405	Intermediate Similarity	NPC65489
0.7405	Intermediate Similarity	NPC115998
0.7405	Intermediate Similarity	NPC39753
0.7403	Intermediate Similarity	NPC170018
0.7403	Intermediate Similarity	NPC76112
0.7403	Intermediate Similarity	NPC92403
0.7403	Intermediate Similarity	NPC66820
0.7403	Intermediate Similarity	NPC475246
0.7401	Intermediate Similarity	NPC272560
0.7401	Intermediate Similarity	NPC30027
0.7399	Intermediate Similarity	NPC268360
0.7399	Intermediate Similarity	NPC287789
0.7399	Intermediate Similarity	NPC67197
0.7399	Intermediate Similarity	NPC271741
0.7396	Intermediate Similarity	NPC288840
0.7396	Intermediate Similarity	NPC10027
0.7396	Intermediate Similarity	NPC291746
0.7396	Intermediate Similarity	NPC473978
0.7396	Intermediate Similarity	NPC65775
0.7394	Intermediate Similarity	NPC105648
0.7386	Intermediate Similarity	NPC470081
0.7386	Intermediate Similarity	NPC159508
0.7384	Intermediate Similarity	NPC52611
0.7384	Intermediate Similarity	NPC226656
0.7384	Intermediate Similarity	NPC100049
0.7384	Intermediate Similarity	NPC159707
0.7384	Intermediate Similarity	NPC148938
0.7384	Intermediate Similarity	NPC297531
0.7384	Intermediate Similarity	NPC186227
0.7384	Intermediate Similarity	NPC150908
0.7384	Intermediate Similarity	NPC14606
0.7384	Intermediate Similarity	NPC215203
0.7384	Intermediate Similarity	NPC158027
0.7384	Intermediate Similarity	NPC66508
0.7384	Intermediate Similarity	NPC205026

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 NPC472157 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	439
0.1-0.2	1077
0.2-0.3	1614
0.3-0.4	2807
0.4-0.5	1916
0.5-0.6	958
0.6-0.7	285
0.7-0.8	54
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
0.7578	Intermediate Similarity	NPD2346	Discontinued
0.75	Intermediate Similarity	NPD3749	Approved
0.7471	Intermediate Similarity	NPD6959	Discontinued
0.7403	Intermediate Similarity	NPD8312	Approved
0.7403	Intermediate Similarity	NPD8313	Approved
0.7333	Intermediate Similarity	NPD3750	Approved
0.7308	Intermediate Similarity	NPD1203	Approved
0.7296	Intermediate Similarity	NPD2313	Discontinued
0.7294	Intermediate Similarity	NPD3226	Approved
0.7294	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7263	Intermediate Similarity	NPD3751	Discontinued
0.7235	Intermediate Similarity	NPD2370	Clinical (unspecified phase)
0.7232	Intermediate Similarity	NPD3787	Discontinued
0.7202	Intermediate Similarity	NPD1511	Approved
0.72	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.716	Intermediate Similarity	NPD1578	Phase 2
0.716	Intermediate Similarity	NPD1184	Approved
0.7152	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD2344	Approved
0.7152	Intermediate Similarity	NPD2798	Approved
0.7151	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD7768	Phase 2
0.7127	Intermediate Similarity	NPD7054	Approved
0.7126	Intermediate Similarity	NPD7819	Suspended
0.7118	Intermediate Similarity	NPD1512	Approved
0.7108	Intermediate Similarity	NPD1549	Phase 2
0.7091	Intermediate Similarity	NPD2935	Discontinued
0.7088	Intermediate Similarity	NPD7074	Phase 3
0.7088	Intermediate Similarity	NPD7472	Approved
0.7086	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7069	Intermediate Similarity	NPD1934	Approved
0.7059	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7056	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7056	Intermediate Similarity	NPD6166	Phase 2
0.7056	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7055	Intermediate Similarity	NPD1933	Approved
0.7055	Intermediate Similarity	NPD447	Suspended
0.7053	Intermediate Similarity	NPD4360	Phase 2
0.7053	Intermediate Similarity	NPD4363	Phase 3
0.7049	Intermediate Similarity	NPD6797	Phase 2
0.7039	Intermediate Similarity	NPD6232	Discontinued
0.703	Intermediate Similarity	NPD2799	Discontinued
0.703	Intermediate Similarity	NPD3748	Approved
0.7029	Intermediate Similarity	NPD2801	Approved
0.7029	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7024	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7017	Intermediate Similarity	NPD7473	Discontinued
0.7011	Intermediate Similarity	NPD7411	Suspended
0.7011	Intermediate Similarity	NPD6559	Discontinued
0.7011	Intermediate Similarity	NPD7251	Discontinued
0.7006	Intermediate Similarity	NPD9717	Approved
0.7006	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD7390	Discontinued
0.6989	Remote Similarity	NPD2379	Clinical (unspecified phase)
0.6989	Remote Similarity	NPD5402	Approved
0.6988	Remote Similarity	NPD1551	Phase 2
0.6988	Remote Similarity	NPD5404	Approved
0.6988	Remote Similarity	NPD5405	Approved
0.6988	Remote Similarity	NPD5406	Approved
0.6988	Remote Similarity	NPD5408	Approved
0.6982	Remote Similarity	NPD2309	Approved
0.6981	Remote Similarity	NPD1470	Approved
0.6978	Remote Similarity	NPD3818	Discontinued
0.6973	Remote Similarity	NPD7808	Phase 3
0.6973	Remote Similarity	NPD4338	Clinical (unspecified phase)
0.697	Remote Similarity	NPD4978	Clinical (unspecified phase)
0.6951	Remote Similarity	NPD1899	Clinical (unspecified phase)
0.6949	Remote Similarity	NPD4868	Clinical (unspecified phase)
0.6947	Remote Similarity	NPD7879	Clinical (unspecified phase)
0.6943	Remote Similarity	NPD1201	Approved
0.6943	Remote Similarity	NPD1547	Clinical (unspecified phase)
0.694	Remote Similarity	NPD7804	Clinical (unspecified phase)
0.6932	Remote Similarity	NPD1465	Phase 2
0.6931	Remote Similarity	NPD8397	Clinical (unspecified phase)
0.6928	Remote Similarity	NPD1510	Phase 2
0.6923	Remote Similarity	NPD7003	Approved
0.6901	Remote Similarity	NPD7041	Phase 2
0.6901	Remote Similarity	NPD7040	Clinical (unspecified phase)
0.6882	Remote Similarity	NPD2354	Approved
0.6875	Remote Similarity	NPD2797	Approved
0.6871	Remote Similarity	NPD411	Approved
0.6871	Remote Similarity	NPD3268	Approved
0.686	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6857	Remote Similarity	NPD4380	Phase 2
0.6852	Remote Similarity	NPD6832	Phase 2
0.6848	Remote Similarity	NPD5844	Phase 1
0.6826	Remote Similarity	NPD4308	Phase 3
0.6798	Remote Similarity	NPD8438	Clinical (unspecified phase)
0.6788	Remote Similarity	NPD1240	Approved
0.6782	Remote Similarity	NPD5403	Approved
0.678	Remote Similarity	NPD6844	Discontinued
0.6776	Remote Similarity	NPD2403	Approved
0.6774	Remote Similarity	NPD7993	Clinical (unspecified phase)
0.6774	Remote Similarity	NPD405	Clinical (unspecified phase)
0.6768	Remote Similarity	NPD3764	Approved
0.6763	Remote Similarity	NPD5401	Approved
0.676	Remote Similarity	NPD3882	Suspended
0.6753	Remote Similarity	NPD4362	Clinical (unspecified phase)
0.6753	Remote Similarity	NPD4361	Phase 2
0.6746	Remote Similarity	NPD2353	Approved
0.6746	Remote Similarity	NPD2343	Clinical (unspecified phase)
0.6746	Remote Similarity	NPD2355	Clinical (unspecified phase)
0.6742	Remote Similarity	NPD8455	Phase 2
0.6726	Remote Similarity	NPD1509	Clinical (unspecified phase)
0.6724	Remote Similarity	NPD1940	Clinical (unspecified phase)
0.6722	Remote Similarity	NPD7075	Discontinued
0.6708	Remote Similarity	NPD3225	Approved
0.6707	Remote Similarity	NPD1607	Approved
0.6705	Remote Similarity	NPD7458	Discontinued
0.6704	Remote Similarity	NPD3817	Phase 2
0.6701	Remote Similarity	NPD6777	Approved
0.6701	Remote Similarity	NPD6781	Approved
0.6701	Remote Similarity	NPD6779	Approved
0.6701	Remote Similarity	NPD6780	Approved
0.6701	Remote Similarity	NPD6782	Approved
0.6701	Remote Similarity	NPD6778	Approved
0.6701	Remote Similarity	NPD6776	Approved
0.6687	Remote Similarity	NPD454	Approved
0.6686	Remote Similarity	NPD6099	Approved
0.6686	Remote Similarity	NPD6100	Approved
0.6686	Remote Similarity	NPD2796	Approved
0.6686	Remote Similarity	NPD1501	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD3266	Approved
0.6667	Remote Similarity	NPD2532	Approved
0.6667	Remote Similarity	NPD2533	Approved
0.6667	Remote Similarity	NPD2534	Approved
0.6667	Remote Similarity	NPD4287	Approved
0.6667	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD3267	Approved
0.6667	Remote Similarity	NPD4972	Discontinued
0.6667	Remote Similarity	NPD2800	Approved
0.665	Remote Similarity	NPD7871	Phase 2
0.665	Remote Similarity	NPD7870	Phase 2
0.6648	Remote Similarity	NPD5494	Approved
0.6648	Remote Similarity	NPD7096	Clinical (unspecified phase)
0.6633	Remote Similarity	NPD6823	Phase 2
0.6629	Remote Similarity	NPD6273	Approved
0.6628	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6618	Remote Similarity	NPD7782	Clinical (unspecified phase)
0.6618	Remote Similarity	NPD7783	Phase 2
0.6609	Remote Similarity	NPD6799	Approved
0.6606	Remote Similarity	NPD4625	Phase 3
0.6601	Remote Similarity	NPD8151	Discontinued
0.66	Remote Similarity	NPD7698	Approved
0.66	Remote Similarity	NPD7697	Approved
0.66	Remote Similarity	NPD7435	Discontinued
0.66	Remote Similarity	NPD7696	Phase 3
0.659	Remote Similarity	NPD3887	Approved
0.6587	Remote Similarity	NPD4307	Phase 2
0.6584	Remote Similarity	NPD4878	Approved
0.6561	Remote Similarity	NPD9493	Approved
0.6552	Remote Similarity	NPD5058	Phase 3
0.655	Remote Similarity	NPD1471	Phase 3
0.6545	Remote Similarity	NPD4908	Phase 1
0.6528	Remote Similarity	NPD5800	Discontinued
0.6524	Remote Similarity	NPD1019	Discontinued
0.6524	Remote Similarity	NPD7177	Discontinued
0.6519	Remote Similarity	NPD4288	Approved
0.6519	Remote Similarity	NPD2296	Approved
0.6512	Remote Similarity	NPD5958	Discontinued
0.6512	Remote Similarity	NPD4534	Discontinued
0.6505	Remote Similarity	NPD5822	Clinical (unspecified phase)
0.6488	Remote Similarity	NPD943	Approved
0.6481	Remote Similarity	NPD1481	Phase 2
0.6481	Remote Similarity	NPD1608	Approved
0.648	Remote Similarity	NPD6599	Discontinued
0.648	Remote Similarity	NPD6212	Phase 3
0.648	Remote Similarity	NPD6214	Clinical (unspecified phase)
0.648	Remote Similarity	NPD6213	Phase 3
0.6477	Remote Similarity	NPD7422	Clinical (unspecified phase)
0.6471	Remote Similarity	NPD4538	Approved
0.6471	Remote Similarity	NPD4537	Clinical (unspecified phase)
0.6471	Remote Similarity	NPD7701	Phase 2
0.6471	Remote Similarity	NPD4536	Approved
0.6467	Remote Similarity	NPD4907	Clinical (unspecified phase)
0.6463	Remote Similarity	NPD1164	Approved
0.6447	Remote Similarity	NPD6534	Approved
0.6447	Remote Similarity	NPD6535	Approved
0.6436	Remote Similarity	NPD7228	Approved
0.6433	Remote Similarity	NPD5960	Phase 3
0.6433	Remote Similarity	NPD651	Clinical (unspecified phase)
0.6433	Remote Similarity	NPD5588	Approved
0.6432	Remote Similarity	NPD7199	Phase 2
0.642	Remote Similarity	NPD1535	Discovery
0.642	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6413	Remote Similarity	NPD6234	Discontinued
0.6409	Remote Similarity	NPD6801	Discontinued
0.6409	Remote Similarity	NPD37	Approved
0.6408	Remote Similarity	NPD7875	Clinical (unspecified phase)
0.6408	Remote Similarity	NPD7874	Approved
0.6407	Remote Similarity	NPD2598	Clinical (unspecified phase)
0.6404	Remote Similarity	NPD920	Approved
0.6404	Remote Similarity	NPD6980	Clinical (unspecified phase)
0.6402	Remote Similarity	NPD1283	Approved
0.6398	Remote Similarity	NPD7229	Phase 3
0.6393	Remote Similarity	NPD4965	Approved
0.6393	Remote Similarity	NPD4967	Phase 2
0.6393	Remote Similarity	NPD4966	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