NPASS Compound

Structure

NPC470871 OpenBabel07101719512D 32 34 0 0 1 0 0 0 0 0999 V2000 -5.1962 2.0000 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 -6.0622 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9282 2.0000 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 -7.7942 1.5000 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 -8.6603 2.0000 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 -9.5263 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -11.2583 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -12.1244 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -1.0000 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 -12.8675 3.6691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -12.4608 4.5827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -10.3923 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -10.3923 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -12.1244 3.0000 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 1.7321 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -1.0000 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -11.2583 3.5000 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 0.0000 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -11.4662 4.4781 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 0 0 0 1 3 1 0 0 0 0 2 4 1 0 0 0 0 3 5 1 0 0 0 0 4 6 1 0 0 0 0 5 7 1 0 0 0 0 6 8 1 0 0 0 0 7 9 1 0 0 0 0 8 10 1 0 0 0 0 9 11 1 0 0 0 0 10 12 1 0 0 0 0 11 20 1 0 0 0 0 12 22 1 0 0 0 0 13 14 2 0 0 0 0 13 20 1 0 0 0 0 14 21 1 0 0 0 0 15 16 1 0 0 0 0 15 23 1 0 0 0 0 16 24 1 0 0 0 0 17 18 1 0 0 0 0 17 21 1 0 0 0 0 18 32 1 0 0 0 0 19 20 2 0 0 0 0 19 25 1 0 0 0 0 21 25 2 0 0 0 0 22 26 1 0 0 0 0 22 28 2 0 0 0 0 23 26 2 0 0 0 0 23 29 1 0 0 0 0 24 27 1 0 0 0 0 24 30 1 0 0 0 0 25 32 1 0 0 0 0 26 27 1 0 0 0 0 27 31 2 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	442.27
Volume:	478.011
LogP:	6.765
LogD:	4.093
LogS:	-3.289
# Rotatable Bonds:	14
TPSA:	90.15
# H-Bond Aceptor:	5
# H-Bond Donor:	4
# Rings:	3
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.156
Synthetic Accessibility Score:	3.046
Fsp3:	0.556
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.255
MDCK Permeability:	1.5318692021537572e-05
Pgp-inhibitor:	0.64
Pgp-substrate:	0.007
Human Intestinal Absorption (HIA):	0.02
20% Bioavailability (F20%):	1.0
30% Bioavailability (F30%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.007
Plasma Protein Binding (PPB):	99.99508666992188%
Volume Distribution (VD):	1.273
Pgp-substrate:	0.4846608340740204%

ADMET: Metabolism

CYP1A2-inhibitor:	0.389
CYP1A2-substrate:	0.208
CYP2C19-inhibitor:	0.726
CYP2C19-substrate:	0.059
CYP2C9-inhibitor:	0.178
CYP2C9-substrate:	0.966
CYP2D6-inhibitor:	0.784
CYP2D6-substrate:	0.905
CYP3A4-inhibitor:	0.182
CYP3A4-substrate:	0.125

ADMET: Excretion

Clearance (CL):	7.341
Half-life (T1/2):	0.576

ADMET: Toxicity

hERG Blockers:	0.049
Human Hepatotoxicity (H-HT):	0.025
Drug-inuced Liver Injury (DILI):	0.023
AMES Toxicity:	0.602
Rat Oral Acute Toxicity:	0.115
Maximum Recommended Daily Dose:	0.654
Skin Sensitization:	0.972
Carcinogencity:	0.047
Eye Corrosion:	0.003
Eye Irritation:	0.907
Respiratory Toxicity:	0.239

Download Data

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

Natural Product: NPC470871

Natural Product ID:	NPC470871
*Common Name:**	MRQNTXNVJYAQEC-UHFFFAOYSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	MRQNTXNVJYAQEC-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C27H38O5/c28-22(26-23(29)15-16-24(30)27(26)31)12-10-8-6-4-2-1-3-5-7-9-11-20-13-14-21-17-18-32-25(21)19-20/h13-14,19,24,29-30H,1-12,15-18H2
SMILES:	OC1CCC(=C(C1=O)C(=O)CCCCCCCCCCCCc1ccc2c(c1)OCC2)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL227266
PubChem CID:	n.a.
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0004189] Coumarans

*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
NPO17040	Peperomia duclouxii	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16499322]
NPO17040	Peperomia duclouxii	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17358082]
NPO17040	Peperomia duclouxii	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17547458]
NPO17040	Peperomia duclouxii	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO17040	Peperomia duclouxii	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO17040	Peperomia duclouxii	Species	Piperaceae	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
NPT81	Cell Line	A549	Homo sapiens	IC50	=	43.3	ug.mL-1	PMID[504052]
NPT81	Cell Line	A549	Homo sapiens	IC50	=	27.2	ug.mL-1	PMID[504052]

☑ 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 NPC470871 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	317
0.1-0.2	1295
0.2-0.3	3323
0.3-0.4	8185
0.4-0.5	10901
0.5-0.6	4150
0.6-0.7	11505
0.7-0.8	2967
0.8-0.85	47
0.85-0.9	6
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.8741	High Similarity	NPC477210
0.8571	High Similarity	NPC201419
0.8561	High Similarity	NPC470855
0.8519	High Similarity	NPC474246
0.8519	High Similarity	NPC474143
0.8507	High Similarity	NPC59654
0.85	High Similarity	NPC475044
0.85	High Similarity	NPC475063
0.8496	Intermediate Similarity	NPC477214
0.8496	Intermediate Similarity	NPC477212
0.8496	Intermediate Similarity	NPC319422
0.8496	Intermediate Similarity	NPC477211
0.8489	Intermediate Similarity	NPC474943
0.8489	Intermediate Similarity	NPC475005
0.8478	Intermediate Similarity	NPC194847
0.8478	Intermediate Similarity	NPC21797
0.8444	Intermediate Similarity	NPC475880
0.8429	Intermediate Similarity	NPC475045
0.837	Intermediate Similarity	NPC271832
0.8369	Intermediate Similarity	NPC477535
0.8357	Intermediate Similarity	NPC475028
0.8357	Intermediate Similarity	NPC476025
0.8346	Intermediate Similarity	NPC477213
0.8298	Intermediate Similarity	NPC477408
0.8239	Intermediate Similarity	NPC477537
0.8227	Intermediate Similarity	NPC98395
0.8201	Intermediate Similarity	NPC265793
0.8188	Intermediate Similarity	NPC251549
0.8156	Intermediate Similarity	NPC130976
0.8143	Intermediate Similarity	NPC475011
0.8138	Intermediate Similarity	NPC477409
0.8125	Intermediate Similarity	NPC474154
0.8125	Intermediate Similarity	NPC329493
0.8116	Intermediate Similarity	NPC324488
0.8116	Intermediate Similarity	NPC477412
0.8085	Intermediate Similarity	NPC278832
0.8085	Intermediate Similarity	NPC64157
0.8085	Intermediate Similarity	NPC232996
0.8058	Intermediate Similarity	NPC329427
0.8058	Intermediate Similarity	NPC317601
0.8058	Intermediate Similarity	NPC312560
0.8015	Intermediate Similarity	NPC152159
0.8014	Intermediate Similarity	NPC476018
0.8014	Intermediate Similarity	NPC471600
0.8014	Intermediate Similarity	NPC469385
0.8014	Intermediate Similarity	NPC475029
0.8	Intermediate Similarity	NPC477536
0.7986	Intermediate Similarity	NPC473982
0.7986	Intermediate Similarity	NPC477706
0.7986	Intermediate Similarity	NPC205360
0.7985	Intermediate Similarity	NPC49441
0.7971	Intermediate Similarity	NPC939
0.7961	Intermediate Similarity	NPC326910
0.7955	Intermediate Similarity	NPC98748
0.7945	Intermediate Similarity	NPC158871
0.7945	Intermediate Similarity	NPC316691
0.7929	Intermediate Similarity	NPC477406
0.7917	Intermediate Similarity	NPC475012
0.7917	Intermediate Similarity	NPC268691
0.7914	Intermediate Similarity	NPC477705
0.7914	Intermediate Similarity	NPC196621
0.7914	Intermediate Similarity	NPC477694
0.7902	Intermediate Similarity	NPC477534
0.7895	Intermediate Similarity	NPC193200
0.7895	Intermediate Similarity	NPC84721
0.7895	Intermediate Similarity	NPC301233
0.7891	Intermediate Similarity	NPC469642
0.7891	Intermediate Similarity	NPC471451
0.7887	Intermediate Similarity	NPC22644
0.7887	Intermediate Similarity	NPC22222
0.7887	Intermediate Similarity	NPC281513
0.7868	Intermediate Similarity	NPC190086
0.7868	Intermediate Similarity	NPC276962
0.7868	Intermediate Similarity	NPC56332
0.7862	Intermediate Similarity	NPC136649
0.7857	Intermediate Similarity	NPC279596
0.7857	Intermediate Similarity	NPC141549
0.7857	Intermediate Similarity	NPC15083
0.7852	Intermediate Similarity	NPC469425
0.7852	Intermediate Similarity	NPC188997
0.7852	Intermediate Similarity	NPC478163
0.7847	Intermediate Similarity	NPC475104
0.7846	Intermediate Similarity	NPC114144
0.7843	Intermediate Similarity	NPC478159
0.7843	Intermediate Similarity	NPC478161
0.7838	Intermediate Similarity	NPC212697
0.7838	Intermediate Similarity	NPC97662
0.7836	Intermediate Similarity	NPC322569
0.7829	Intermediate Similarity	NPC60211
0.7826	Intermediate Similarity	NPC142087
0.7826	Intermediate Similarity	NPC470841
0.7826	Intermediate Similarity	NPC95034
0.781	Intermediate Similarity	NPC224657
0.781	Intermediate Similarity	NPC470858
0.7808	Intermediate Similarity	NPC104956
0.7801	Intermediate Similarity	NPC474340
0.7801	Intermediate Similarity	NPC118253
0.78	Intermediate Similarity	NPC228012
0.78	Intermediate Similarity	NPC474556
0.7794	Intermediate Similarity	NPC261992
0.7794	Intermediate Similarity	NPC11799
0.7794	Intermediate Similarity	NPC141252
0.7793	Intermediate Similarity	NPC322021
0.7786	Intermediate Similarity	NPC278787
0.7786	Intermediate Similarity	NPC282230
0.7786	Intermediate Similarity	NPC7569
0.7786	Intermediate Similarity	NPC470725
0.7786	Intermediate Similarity	NPC146615
0.7786	Intermediate Similarity	NPC183348
0.7785	Intermediate Similarity	NPC308799
0.7778	Intermediate Similarity	NPC301341
0.7778	Intermediate Similarity	NPC476165
0.7778	Intermediate Similarity	NPC284184
0.7778	Intermediate Similarity	NPC470331
0.777	Intermediate Similarity	NPC89664
0.777	Intermediate Similarity	NPC274085
0.7763	Intermediate Similarity	NPC175617
0.7762	Intermediate Similarity	NPC51087
0.7762	Intermediate Similarity	NPC291119
0.7762	Intermediate Similarity	NPC217914
0.7762	Intermediate Similarity	NPC161856
0.7762	Intermediate Similarity	NPC281169
0.7761	Intermediate Similarity	NPC232295
0.7756	Intermediate Similarity	NPC313368
0.7744	Intermediate Similarity	NPC283616
0.7742	Intermediate Similarity	NPC294300
0.7742	Intermediate Similarity	NPC281137
0.7742	Intermediate Similarity	NPC317900
0.7742	Intermediate Similarity	NPC476404
0.7742	Intermediate Similarity	NPC282390
0.774	Intermediate Similarity	NPC473499
0.7737	Intermediate Similarity	NPC147896
0.7733	Intermediate Similarity	NPC252208
0.7733	Intermediate Similarity	NPC113428
0.7733	Intermediate Similarity	NPC61284
0.773	Intermediate Similarity	NPC196979
0.773	Intermediate Similarity	NPC470976
0.773	Intermediate Similarity	NPC470977
0.7721	Intermediate Similarity	NPC204535
0.7721	Intermediate Similarity	NPC46586
0.7714	Intermediate Similarity	NPC170546
0.7714	Intermediate Similarity	NPC66246
0.7712	Intermediate Similarity	NPC321363
0.7712	Intermediate Similarity	NPC44606
0.7712	Intermediate Similarity	NPC253904
0.7712	Intermediate Similarity	NPC471347
0.7712	Intermediate Similarity	NPC471349
0.7708	Intermediate Similarity	NPC471670
0.7708	Intermediate Similarity	NPC266245
0.7698	Intermediate Similarity	NPC298884
0.7697	Intermediate Similarity	NPC475718
0.7697	Intermediate Similarity	NPC475717
0.7692	Intermediate Similarity	NPC27394
0.7687	Intermediate Similarity	NPC32152
0.7687	Intermediate Similarity	NPC43435
0.7682	Intermediate Similarity	NPC191634
0.7676	Intermediate Similarity	NPC470160
0.7676	Intermediate Similarity	NPC280476
0.7676	Intermediate Similarity	NPC119985
0.7673	Intermediate Similarity	NPC316262
0.7673	Intermediate Similarity	NPC314653
0.7671	Intermediate Similarity	NPC470407
0.7671	Intermediate Similarity	NPC18904
0.7671	Intermediate Similarity	NPC112757
0.7667	Intermediate Similarity	NPC469758
0.7664	Intermediate Similarity	NPC474130
0.7664	Intermediate Similarity	NPC244876
0.7664	Intermediate Similarity	NPC93730
0.766	Intermediate Similarity	NPC163169
0.766	Intermediate Similarity	NPC172673
0.766	Intermediate Similarity	NPC253488
0.766	Intermediate Similarity	NPC123
0.7655	Intermediate Similarity	NPC470721
0.7655	Intermediate Similarity	NPC156888
0.7655	Intermediate Similarity	NPC6100
0.7655	Intermediate Similarity	NPC470722
0.7655	Intermediate Similarity	NPC98804
0.7655	Intermediate Similarity	NPC309452
0.7651	Intermediate Similarity	NPC105381
0.7651	Intermediate Similarity	NPC10302
0.7643	Intermediate Similarity	NPC472961
0.7643	Intermediate Similarity	NPC472962
0.7635	Intermediate Similarity	NPC133585
0.7635	Intermediate Similarity	NPC474966
0.7635	Intermediate Similarity	NPC197461
0.7635	Intermediate Similarity	NPC229916
0.7632	Intermediate Similarity	NPC146014
0.7632	Intermediate Similarity	NPC269420
0.763	Intermediate Similarity	NPC31314
0.763	Intermediate Similarity	NPC168050
0.763	Intermediate Similarity	NPC474874
0.763	Intermediate Similarity	NPC193193
0.763	Intermediate Similarity	NPC474131
0.7628	Intermediate Similarity	NPC473282
0.7628	Intermediate Similarity	NPC104380
0.7628	Intermediate Similarity	NPC217602
0.7622	Intermediate Similarity	NPC263817
0.7622	Intermediate Similarity	NPC472591
0.7622	Intermediate Similarity	NPC59459
0.7616	Intermediate Similarity	NPC478018

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 NPC470871 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	273
0.1-0.2	888
0.2-0.3	1511
0.3-0.4	2497
0.4-0.5	2066
0.5-0.6	1225
0.6-0.7	590
0.7-0.8	100
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
0.7872	Intermediate Similarity	NPD6355	Discontinued
0.7761	Intermediate Similarity	NPD1778	Approved
0.7704	Intermediate Similarity	NPD3496	Discontinued
0.766	Intermediate Similarity	NPD6798	Discontinued
0.7652	Intermediate Similarity	NPD6671	Approved
0.7634	Intermediate Similarity	NPD1241	Discontinued
0.7603	Intermediate Similarity	NPD2346	Discontinued
0.76	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7551	Intermediate Similarity	NPD2424	Discontinued
0.7535	Intermediate Similarity	NPD2313	Discontinued
0.7535	Intermediate Similarity	NPD3268	Approved
0.7518	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7484	Intermediate Similarity	NPD6844	Discontinued
0.7483	Intermediate Similarity	NPD5763	Approved
0.7483	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7483	Intermediate Similarity	NPD2344	Approved
0.7483	Intermediate Similarity	NPD5762	Approved
0.7483	Intermediate Similarity	NPD6233	Phase 2
0.745	Intermediate Similarity	NPD4628	Phase 3
0.745	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7429	Intermediate Similarity	NPD2797	Approved
0.7415	Intermediate Similarity	NPD6100	Approved
0.7415	Intermediate Similarity	NPD6099	Approved
0.7413	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7413	Intermediate Similarity	NPD1699	Clinical (unspecified phase)
0.7403	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7389	Intermediate Similarity	NPD5402	Approved
0.7368	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7365	Intermediate Similarity	NPD6004	Phase 3
0.7365	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.7365	Intermediate Similarity	NPD6002	Phase 3
0.7365	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.7365	Intermediate Similarity	NPD6005	Phase 3
0.7365	Intermediate Similarity	NPD1471	Phase 3
0.7347	Intermediate Similarity	NPD7033	Discontinued
0.7347	Intermediate Similarity	NPD2799	Discontinued
0.7342	Intermediate Similarity	NPD3882	Suspended
0.7338	Intermediate Similarity	NPD1608	Approved
0.7338	Intermediate Similarity	NPD3972	Approved
0.7329	Intermediate Similarity	NPD6653	Approved
0.7324	Intermediate Similarity	NPD2861	Phase 2
0.7305	Intermediate Similarity	NPD3266	Approved
0.7305	Intermediate Similarity	NPD3267	Approved
0.7299	Intermediate Similarity	NPD5691	Approved
0.7299	Intermediate Similarity	NPD1651	Approved
0.7297	Intermediate Similarity	NPD6032	Approved
0.7297	Intermediate Similarity	NPD2935	Discontinued
0.729	Intermediate Similarity	NPD3226	Approved
0.7285	Intermediate Similarity	NPD2309	Approved
0.7273	Intermediate Similarity	NPD6832	Phase 2
0.7267	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7254	Intermediate Similarity	NPD5647	Approved
0.7248	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7248	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7246	Intermediate Similarity	NPD4626	Approved
0.7241	Intermediate Similarity	NPD4062	Phase 3
0.7234	Intermediate Similarity	NPD6696	Suspended
0.723	Intermediate Similarity	NPD4308	Phase 3
0.7226	Intermediate Similarity	NPD1894	Discontinued
0.7222	Intermediate Similarity	NPD7095	Approved
0.7219	Intermediate Similarity	NPD4110	Phase 3
0.7219	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.7215	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7215	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7208	Intermediate Similarity	NPD6273	Approved
0.72	Intermediate Similarity	NPD1549	Phase 2
0.7192	Intermediate Similarity	NPD4060	Phase 1
0.7183	Intermediate Similarity	NPD6362	Approved
0.7181	Intermediate Similarity	NPD2796	Approved
0.7176	Intermediate Similarity	NPD290	Approved
0.7174	Intermediate Similarity	NPD5585	Approved
0.7172	Intermediate Similarity	NPD7985	Registered
0.7172	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7172	Intermediate Similarity	NPD411	Approved
0.7164	Intermediate Similarity	NPD7843	Approved
0.7152	Intermediate Similarity	NPD3818	Discontinued
0.7152	Intermediate Similarity	NPD2800	Approved
0.7152	Intermediate Similarity	NPD1934	Approved
0.7152	Intermediate Similarity	NPD3751	Discontinued
0.7143	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD447	Suspended
0.7143	Intermediate Similarity	NPD2533	Approved
0.7143	Intermediate Similarity	NPD1611	Approved
0.7143	Intermediate Similarity	NPD2534	Approved
0.7143	Intermediate Similarity	NPD2532	Approved
0.7143	Intermediate Similarity	NPD1535	Discovery
0.7134	Intermediate Similarity	NPD6599	Discontinued
0.7134	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7134	Intermediate Similarity	NPD6166	Phase 2
0.7134	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7133	Intermediate Similarity	NPD6800	Clinical (unspecified phase)
0.7133	Intermediate Similarity	NPD2798	Approved
0.7132	Intermediate Similarity	NPD7157	Approved
0.7123	Intermediate Similarity	NPD8032	Phase 2
0.7122	Intermediate Similarity	NPD17	Approved
0.7121	Intermediate Similarity	NPD2684	Approved
0.7117	Intermediate Similarity	NPD3787	Discontinued
0.7113	Intermediate Similarity	NPD3225	Approved
0.7113	Intermediate Similarity	NPD1283	Approved
0.7107	Intermediate Similarity	NPD2801	Approved
0.7107	Intermediate Similarity	NPD7819	Suspended
0.7105	Intermediate Similarity	NPD7982	Clinical (unspecified phase)
0.7099	Intermediate Similarity	NPD968	Approved
0.7099	Intermediate Similarity	NPD5494	Approved
0.7097	Intermediate Similarity	NPD1512	Approved
0.7092	Intermediate Similarity	NPD2235	Phase 2
0.7092	Intermediate Similarity	NPD1481	Phase 2
0.7092	Intermediate Similarity	NPD9717	Approved
0.7092	Intermediate Similarity	NPD2231	Phase 2
0.7086	Intermediate Similarity	NPD5958	Discontinued
0.7081	Intermediate Similarity	NPD7075	Discontinued
0.7078	Intermediate Similarity	NPD6799	Approved
0.7076	Intermediate Similarity	NPD8434	Phase 2
0.7075	Intermediate Similarity	NPD2979	Phase 3
0.7075	Intermediate Similarity	NPD4307	Phase 2
0.7075	Intermediate Similarity	NPD4140	Approved
0.707	Intermediate Similarity	NPD2651	Approved
0.707	Intermediate Similarity	NPD2649	Approved
0.7067	Intermediate Similarity	NPD1551	Phase 2
0.7063	Intermediate Similarity	NPD1203	Approved
0.7063	Intermediate Similarity	NPD3817	Phase 2
0.7055	Intermediate Similarity	NPD8127	Discontinued
0.7051	Intermediate Similarity	NPD5403	Approved
0.7047	Intermediate Similarity	NPD7097	Phase 1
0.7042	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7042	Intermediate Similarity	NPD4749	Approved
0.7034	Intermediate Similarity	NPD2614	Approved
0.7032	Intermediate Similarity	NPD5401	Approved
0.7029	Intermediate Similarity	NPD5536	Phase 2
0.7025	Intermediate Similarity	NPD4380	Phase 2
0.7019	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7014	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7014	Intermediate Similarity	NPD558	Phase 2
0.7006	Intermediate Similarity	NPD5844	Phase 1
0.7	Intermediate Similarity	NPD1510	Phase 2
0.6993	Remote Similarity	NPD1876	Approved
0.6993	Remote Similarity	NPD3750	Approved
0.6982	Remote Similarity	NPD6559	Discontinued
0.698	Remote Similarity	NPD1607	Approved
0.6975	Remote Similarity	NPD4381	Clinical (unspecified phase)
0.6974	Remote Similarity	NPD4534	Discontinued
0.6968	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6968	Remote Similarity	NPD1511	Approved
0.6966	Remote Similarity	NPD2237	Approved
0.6962	Remote Similarity	NPD7458	Discontinued
0.6957	Remote Similarity	NPD7340	Approved
0.6957	Remote Similarity	NPD8443	Clinical (unspecified phase)
0.6954	Remote Similarity	NPD4476	Approved
0.6954	Remote Similarity	NPD1501	Clinical (unspecified phase)
0.6954	Remote Similarity	NPD4477	Approved
0.6951	Remote Similarity	NPD1247	Approved
0.6951	Remote Similarity	NPD6959	Discontinued
0.6948	Remote Similarity	NPD6190	Approved
0.6948	Remote Similarity	NPD3887	Approved
0.6941	Remote Similarity	NPD4338	Clinical (unspecified phase)
0.694	Remote Similarity	NPD2067	Discontinued
0.6937	Remote Similarity	NPD6801	Discontinued
0.6928	Remote Similarity	NPD4575	Clinical (unspecified phase)
0.6928	Remote Similarity	NPD5698	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD4661	Approved
0.6923	Remote Similarity	NPD4359	Approved
0.6923	Remote Similarity	NPD4662	Approved
0.6923	Remote Similarity	NPD7993	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD5327	Phase 3
0.6919	Remote Similarity	NPD8055	Clinical (unspecified phase)
0.6913	Remote Similarity	NPD4622	Approved
0.6913	Remote Similarity	NPD5735	Approved
0.6913	Remote Similarity	NPD4618	Approved
0.6909	Remote Similarity	NPD7229	Phase 3
0.6905	Remote Similarity	NPD7804	Clinical (unspecified phase)
0.6901	Remote Similarity	NPD8313	Approved
0.6901	Remote Similarity	NPD1091	Approved
0.6901	Remote Similarity	NPD8312	Approved
0.6901	Remote Similarity	NPD1281	Approved
0.6897	Remote Similarity	NPD1019	Discontinued
0.6894	Remote Similarity	NPD9697	Approved
0.6887	Remote Similarity	NPD3748	Approved
0.6887	Remote Similarity	NPD3299	Clinical (unspecified phase)
0.6883	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.6882	Remote Similarity	NPD7251	Discontinued
0.6879	Remote Similarity	NPD3412	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD8651	Approved
0.6867	Remote Similarity	NPD3926	Phase 2
0.6864	Remote Similarity	NPD7074	Phase 3
0.6863	Remote Similarity	NPD2897	Discontinued
0.6861	Remote Similarity	NPD1398	Phase 1
0.6852	Remote Similarity	NPD5616	Clinical (unspecified phase)
0.6849	Remote Similarity	NPD9494	Approved
0.6849	Remote Similarity	NPD1712	Approved
0.6846	Remote Similarity	NPD1613	Approved
0.6846	Remote Similarity	NPD3140	Approved
0.6846	Remote Similarity	NPD3142	Approved
0.6846	Remote Similarity	NPD1240	Approved
0.6846	Remote Similarity	NPD1612	Clinical (unspecified phase)
0.6845	Remote Similarity	NPD2163	Approved
0.6845	Remote Similarity	NPD7893	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD2438	Suspended
0.6842	Remote Similarity	NPD7808	Phase 3
0.6839	Remote Similarity	NPD2354	Approved
0.6835	Remote Similarity	NPD405	Clinical (unspecified phase)

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