NPASS Compound

Structure

NPC471004 OpenBabel07101718302D 38 44 0 0 1 0 0 0 0 0999 V2000 -2.8045 2.1697 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1261 0.3445 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3653 0.9309 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6344 1.7070 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3534 -1.6289 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5839 -1.3661 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9579 1.0324 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1239 2.9658 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4647 -3.3528 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7326 -3.3528 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4408 -0.1931 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0115 2.5052 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5540 0.4793 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4647 -4.3528 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7326 -4.3528 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3872 -0.5163 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4166 -1.8110 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8288 0.8711 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5986 -2.8528 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8410 -0.9933 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8411 -0.9783 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.5961 -0.5531 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1809 0.7927 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.2812 2.4275 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4652 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.2136 0.9678 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.7326 -0.3528 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.5986 -1.8528 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0563 1.5062 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.3731 -0.3134 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.3260 1.4285 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.5986 -4.8528 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 0.6064 2.8881 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.4647 -1.3528 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.3722 -1.5162 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.4634 -0.0598 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.7326 -1.3528 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5 6 1 0 0 0 0 5 21 1 0 0 0 0 6 22 2 0 0 0 0 7 13 1 0 0 0 0 7 23 1 0 0 0 0 8 12 2 0 0 0 0 8 24 1 0 0 0 0 9 14 1 0 0 0 0 9 19 2 0 0 0 0 10 15 2 0 0 0 0 10 19 1 0 0 0 0 11 16 2 0 0 0 0 11 20 1 0 0 0 0 12 29 1 0 0 0 0 13 30 1 0 0 0 0 14 33 2 0 0 0 0 15 33 1 0 0 0 0 16 36 1 0 0 0 0 17 20 2 0 0 0 0 17 36 1 0 0 0 0 18 29 1 0 0 0 0 18 37 1 0 0 0 0 19 28 1 0 0 0 0 20 21 1 0 0 0 0 21 30 1 6 0 0 0 22 30 1 0 0 0 0 22 31 1 0 0 0 0 23 31 1 1 0 0 0 23 32 1 0 0 0 0 24 32 1 0 0 0 0 24 34 2 0 0 0 0 25 26 1 0 0 0 0 25 27 1 0 0 0 0 25 37 1 6 0 0 0 26 29 1 1 0 0 0 26 32 1 0 0 0 0 27 31 1 6 0 0 0 27 38 1 0 0 0 0 28 35 2 0 0 0 0 28 38 1 0 0 0 0 29 1 1 1 0 0 0 30 2 1 6 0 0 0 31 3 1 1 0 0 0 32 4 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	513.25
Volume:	533.353
LogP:	3.814
LogD:	3.34
LogS:	-4.622
# Rotatable Bonds:	4
TPSA:	78.63
# H-Bond Aceptor:	6
# H-Bond Donor:	0
# Rings:	7
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.375
Synthetic Accessibility Score:	5.226
Fsp3:	0.531
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.115
MDCK Permeability:	2.5303083020844497e-05
Pgp-inhibitor:	1.0
Pgp-substrate:	0.002
Human Intestinal Absorption (HIA):	0.015
20% Bioavailability (F20%):	0.985
30% Bioavailability (F30%):	0.468

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.936
Plasma Protein Binding (PPB):	96.4029312133789%
Volume Distribution (VD):	3.791
Pgp-substrate:	5.717324256896973%

ADMET: Metabolism

CYP1A2-inhibitor:	0.141
CYP1A2-substrate:	0.138
CYP2C19-inhibitor:	0.803
CYP2C19-substrate:	0.171
CYP2C9-inhibitor:	0.827
CYP2C9-substrate:	0.02
CYP2D6-inhibitor:	0.911
CYP2D6-substrate:	0.041
CYP3A4-inhibitor:	0.973
CYP3A4-substrate:	0.578

ADMET: Excretion

Clearance (CL):	11.402
Half-life (T1/2):	0.16

ADMET: Toxicity

hERG Blockers:	0.933
Human Hepatotoxicity (H-HT):	0.399
Drug-inuced Liver Injury (DILI):	0.516
AMES Toxicity:	0.011
Rat Oral Acute Toxicity:	0.978
Maximum Recommended Daily Dose:	0.976
Skin Sensitization:	0.432
Carcinogencity:	0.513
Eye Corrosion:	0.003
Eye Irritation:	0.024
Respiratory Toxicity:	0.981

Download Data

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

Natural Product: NPC471004

Natural Product ID:	NPC471004
*Common Name:**	WLMWPQLTBYZGEW-GATSHTIQSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	WLMWPQLTBYZGEW-GATSHTIQSA-N
Standard InCHI:	InChI=1S/C32H35NO5/c1-29-12-8-24(34)32(4)23-7-13-30(2)21(20-11-16-36-17-20)5-6-22(30)31(23,3)27(25(26(29)32)37-18-29)38-28(35)19-9-14-33-15-10-19/h6,8-12,14-17,21,23,25-27H,5,7,13,18H2,1-4H3/t21-,23-,25+,26-,27+,29-,30-,31-,32-/m0/s1
SMILES:	CC12CCC3C4(C5C(C(C3(C1=CCC2C6=COC=C6)C)OC(=O)C7=CC=NC=C7)OCC5(C=CC4=O)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2335036
PubChem CID:	71567409
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001553] Triterpenoids [CHEMONTID:0002380] Limonoids

*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
NPO5587	Chisocheton ceramicus	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19081726]
NPO5587	Chisocheton ceramicus	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21428417]
NPO5587	Chisocheton ceramicus	Species	Meliaceae	Eukaryota	n.a.	bark	n.a.	PMID[21428417]
NPO5587	Chisocheton ceramicus	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23395661]
NPO5587	Chisocheton ceramicus	Species	Meliaceae	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	1
Others	2

Activity Type	# Activity
NON-MOLECULAR	1
Others	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT2	Others	Unspecified		Ratio CC50/IC50	=	0.9	n.a.	PMID[528808]
NPT27	Others	Unspecified		CC50	=	17200.0	nM	PMID[528808]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	18700.0	nM	PMID[528808]

☑ 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 NPC471004 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	431
0.1-0.2	1781
0.2-0.3	4053
0.3-0.4	11296
0.4-0.5	10380
0.5-0.6	12698
0.6-0.7	1801
0.7-0.8	224
0.8-0.85	24
0.85-0.9	8
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.859	High Similarity	NPC475315
0.859	High Similarity	NPC324619
0.8546	High Similarity	NPC475533
0.8541	High Similarity	NPC473833
0.8528	High Similarity	NPC475301
0.8528	High Similarity	NPC326930
0.8421	Intermediate Similarity	NPC148896
0.8421	Intermediate Similarity	NPC180668
0.8421	Intermediate Similarity	NPC471013
0.8412	Intermediate Similarity	NPC13603
0.8405	Intermediate Similarity	NPC471015
0.839	Intermediate Similarity	NPC328928
0.8369	Intermediate Similarity	NPC53255
0.8369	Intermediate Similarity	NPC85879
0.8365	Intermediate Similarity	NPC470279
0.8355	Intermediate Similarity	NPC10904
0.8159	Intermediate Similarity	NPC471978
0.8133	Intermediate Similarity	NPC471979
0.8037	Intermediate Similarity	NPC4421
0.8036	Intermediate Similarity	NPC26881
0.8	Intermediate Similarity	NPC477907
0.8	Intermediate Similarity	NPC42678
0.8	Intermediate Similarity	NPC477909
0.7982	Intermediate Similarity	NPC477903
0.7965	Intermediate Similarity	NPC124029
0.7956	Intermediate Similarity	NPC477900
0.7956	Intermediate Similarity	NPC477899
0.7955	Intermediate Similarity	NPC264674
0.7946	Intermediate Similarity	NPC235364
0.7937	Intermediate Similarity	NPC477901
0.7928	Intermediate Similarity	NPC6576
0.7928	Intermediate Similarity	NPC75600
0.7928	Intermediate Similarity	NPC212768
0.7928	Intermediate Similarity	NPC473089
0.7928	Intermediate Similarity	NPC62367
0.7928	Intermediate Similarity	NPC473115
0.7928	Intermediate Similarity	NPC158020
0.792	Intermediate Similarity	NPC148860
0.7904	Intermediate Similarity	NPC213143
0.7902	Intermediate Similarity	NPC477912
0.7895	Intermediate Similarity	NPC91125
0.7892	Intermediate Similarity	NPC84815
0.7892	Intermediate Similarity	NPC301368
0.7892	Intermediate Similarity	NPC216428
0.7885	Intermediate Similarity	NPC211920
0.7876	Intermediate Similarity	NPC328154
0.7876	Intermediate Similarity	NPC477902
0.786	Intermediate Similarity	NPC477906
0.786	Intermediate Similarity	NPC96801
0.786	Intermediate Similarity	NPC150698
0.7807	Intermediate Similarity	NPC475600
0.7807	Intermediate Similarity	NPC476110
0.7807	Intermediate Similarity	NPC475631
0.7807	Intermediate Similarity	NPC87152
0.7807	Intermediate Similarity	NPC475601
0.7803	Intermediate Similarity	NPC6981
0.7803	Intermediate Similarity	NPC471016
0.7803	Intermediate Similarity	NPC206343
0.7803	Intermediate Similarity	NPC477908
0.7788	Intermediate Similarity	NPC289086
0.7788	Intermediate Similarity	NPC127720
0.7788	Intermediate Similarity	NPC127026
0.7788	Intermediate Similarity	NPC477788
0.7773	Intermediate Similarity	NPC475644
0.7773	Intermediate Similarity	NPC470486
0.7773	Intermediate Similarity	NPC471190
0.7773	Intermediate Similarity	NPC471977
0.7768	Intermediate Similarity	NPC294579
0.7768	Intermediate Similarity	NPC144779
0.7759	Intermediate Similarity	NPC35208
0.7758	Intermediate Similarity	NPC470306
0.7758	Intermediate Similarity	NPC30570
0.7753	Intermediate Similarity	NPC471980
0.7753	Intermediate Similarity	NPC76565
0.7739	Intermediate Similarity	NPC24019
0.7733	Intermediate Similarity	NPC472555
0.7729	Intermediate Similarity	NPC14116
0.7729	Intermediate Similarity	NPC285411
0.7727	Intermediate Similarity	NPC48042
0.7727	Intermediate Similarity	NPC472550
0.7727	Intermediate Similarity	NPC304179
0.7723	Intermediate Similarity	NPC475408
0.7723	Intermediate Similarity	NPC471014
0.7719	Intermediate Similarity	NPC475137
0.7719	Intermediate Similarity	NPC475498
0.7709	Intermediate Similarity	NPC477911
0.7706	Intermediate Similarity	NPC475596
0.7706	Intermediate Similarity	NPC475303
0.7703	Intermediate Similarity	NPC472553
0.7703	Intermediate Similarity	NPC280473
0.7703	Intermediate Similarity	NPC323551
0.7702	Intermediate Similarity	NPC253482
0.7696	Intermediate Similarity	NPC134384
0.7696	Intermediate Similarity	NPC311196
0.7692	Intermediate Similarity	NPC182907
0.7692	Intermediate Similarity	NPC189903
0.7686	Intermediate Similarity	NPC473506
0.7682	Intermediate Similarity	NPC327769
0.7682	Intermediate Similarity	NPC475426
0.7679	Intermediate Similarity	NPC62844
0.7679	Intermediate Similarity	NPC193361
0.7672	Intermediate Similarity	NPC30456
0.7672	Intermediate Similarity	NPC469748
0.7668	Intermediate Similarity	NPC51008
0.7668	Intermediate Similarity	NPC41724
0.7653	Intermediate Similarity	NPC103230
0.7652	Intermediate Similarity	NPC328186
0.7652	Intermediate Similarity	NPC477787
0.7652	Intermediate Similarity	NPC228377
0.7652	Intermediate Similarity	NPC122968
0.765	Intermediate Similarity	NPC108342
0.7639	Intermediate Similarity	NPC238278
0.7636	Intermediate Similarity	NPC475835
0.7634	Intermediate Similarity	NPC228331
0.7634	Intermediate Similarity	NPC319128
0.7634	Intermediate Similarity	NPC146976
0.7629	Intermediate Similarity	NPC473689
0.7629	Intermediate Similarity	NPC292416
0.7623	Intermediate Similarity	NPC292517
0.7605	Intermediate Similarity	NPC475648
0.7602	Intermediate Similarity	NPC63041
0.76	Intermediate Similarity	NPC477910
0.7598	Intermediate Similarity	NPC250807
0.7598	Intermediate Similarity	NPC57797
0.7597	Intermediate Similarity	NPC244839
0.7597	Intermediate Similarity	NPC319880
0.7597	Intermediate Similarity	NPC320324
0.7589	Intermediate Similarity	NPC236668
0.7576	Intermediate Similarity	NPC146824
0.7566	Intermediate Similarity	NPC162812
0.7565	Intermediate Similarity	NPC473850
0.7564	Intermediate Similarity	NPC237702
0.7564	Intermediate Similarity	NPC22481
0.7554	Intermediate Similarity	NPC316841
0.7543	Intermediate Similarity	NPC475362
0.7533	Intermediate Similarity	NPC187494
0.7533	Intermediate Similarity	NPC319556
0.7532	Intermediate Similarity	NPC475406
0.7532	Intermediate Similarity	NPC170751
0.7532	Intermediate Similarity	NPC90875
0.7511	Intermediate Similarity	NPC166722
0.7511	Intermediate Similarity	NPC165837
0.75	Intermediate Similarity	NPC124313
0.75	Intermediate Similarity	NPC327904
0.75	Intermediate Similarity	NPC38959
0.75	Intermediate Similarity	NPC470189
0.75	Intermediate Similarity	NPC40919
0.749	Intermediate Similarity	NPC84164
0.749	Intermediate Similarity	NPC207283
0.7489	Intermediate Similarity	NPC233727
0.7478	Intermediate Similarity	NPC210434
0.7477	Intermediate Similarity	NPC193238
0.7455	Intermediate Similarity	NPC470020
0.7448	Intermediate Similarity	NPC210296
0.7447	Intermediate Similarity	NPC233334
0.7445	Intermediate Similarity	NPC207531
0.7444	Intermediate Similarity	NPC470190
0.7436	Intermediate Similarity	NPC278525
0.7389	Intermediate Similarity	NPC476467
0.7375	Intermediate Similarity	NPC119134
0.7347	Intermediate Similarity	NPC183537
0.7314	Intermediate Similarity	NPC75179
0.7314	Intermediate Similarity	NPC15406
0.7299	Intermediate Similarity	NPC471997
0.7289	Intermediate Similarity	NPC470280
0.7284	Intermediate Similarity	NPC476090
0.7282	Intermediate Similarity	NPC471003
0.7276	Intermediate Similarity	NPC77878
0.7257	Intermediate Similarity	NPC472752
0.7246	Intermediate Similarity	NPC246381
0.7238	Intermediate Similarity	NPC253675
0.7189	Intermediate Similarity	NPC478045
0.7179	Intermediate Similarity	NPC216612
0.7149	Intermediate Similarity	NPC322482
0.7143	Intermediate Similarity	NPC191489
0.7137	Intermediate Similarity	NPC253314
0.7126	Intermediate Similarity	NPC270515
0.7114	Intermediate Similarity	NPC107123
0.7091	Intermediate Similarity	NPC289786
0.7059	Intermediate Similarity	NPC146724
0.704	Intermediate Similarity	NPC127085
0.7031	Intermediate Similarity	NPC315634
0.7031	Intermediate Similarity	NPC100734
0.7031	Intermediate Similarity	NPC88923
0.7027	Intermediate Similarity	NPC473053
0.7017	Intermediate Similarity	NPC470018
0.7013	Intermediate Similarity	NPC251160
0.7004	Intermediate Similarity	NPC470042
0.7	Intermediate Similarity	NPC290689
0.6987	Remote Similarity	NPC74575
0.6968	Remote Similarity	NPC133140
0.6968	Remote Similarity	NPC195268
0.696	Remote Similarity	NPC134637
0.6951	Remote Similarity	NPC109922
0.6949	Remote Similarity	NPC54066
0.6942	Remote Similarity	NPC49547
0.6932	Remote Similarity	NPC137353
0.6909	Remote Similarity	NPC44354
0.6906	Remote Similarity	NPC135950
0.6892	Remote Similarity	NPC476516

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 NPC471004 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	275
0.1-0.2	616
0.2-0.3	734
0.3-0.4	1805
0.4-0.5	2825
0.5-0.6	2384
0.6-0.7	493
0.7-0.8	18
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
0.7627	Intermediate Similarity	NPD7885	Phase 2
0.7627	Intermediate Similarity	NPD7886	Phase 2
0.7586	Intermediate Similarity	NPD8052	Clinical (unspecified phase)
0.7489	Intermediate Similarity	NPD4989	Phase 2
0.7467	Intermediate Similarity	NPD7069	Discontinued
0.7418	Intermediate Similarity	NPD6257	Clinical (unspecified phase)
0.7397	Intermediate Similarity	NPD8468	Phase 2
0.7376	Intermediate Similarity	NPD6477	Clinical (unspecified phase)
0.7324	Intermediate Similarity	NPD4889	Approved
0.7268	Intermediate Similarity	NPD6635	Approved
0.7236	Intermediate Similarity	NPD6525	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD7708	Approved
0.7137	Intermediate Similarity	NPD3006	Discontinued
0.7137	Intermediate Similarity	NPD7467	Discontinued
0.7089	Intermediate Similarity	NPD8304	Clinical (unspecified phase)
0.7074	Intermediate Similarity	NPD6262	Clinical (unspecified phase)
0.7061	Intermediate Similarity	NPD1483	Discontinued
0.7056	Intermediate Similarity	NPD8350	Clinical (unspecified phase)
0.7054	Intermediate Similarity	NPD6219	Discontinued
0.7043	Intermediate Similarity	NPD7927	Clinical (unspecified phase)
0.7031	Intermediate Similarity	NPD7803	Approved
0.7028	Intermediate Similarity	NPD5482	Discontinued
0.7021	Intermediate Similarity	NPD8479	Phase 2
0.7014	Intermediate Similarity	NPD6361	Phase 2
0.7013	Intermediate Similarity	NPD5866	Approved
0.7009	Intermediate Similarity	NPD7395	Discontinued
0.6983	Remote Similarity	NPD7571	Clinical (unspecified phase)
0.6978	Remote Similarity	NPD5228	Phase 3
0.6976	Remote Similarity	NPD8100	Phase 3
0.6974	Remote Similarity	NPD7010	Phase 3
0.6968	Remote Similarity	NPD3921	Approved
0.6968	Remote Similarity	NPD3923	Approved
0.6968	Remote Similarity	NPD3924	Approved
0.6968	Remote Similarity	NPD3922	Approved
0.6966	Remote Similarity	NPD3326	Clinical (unspecified phase)
0.6939	Remote Similarity	NPD6825	Phase 1
0.6936	Remote Similarity	NPD6568	Discontinued
0.6935	Remote Similarity	NPD5483	Clinical (unspecified phase)
0.693	Remote Similarity	NPD2831	Approved
0.6929	Remote Similarity	NPD4952	Phase 3
0.6917	Remote Similarity	NPD7268	Clinical (unspecified phase)
0.6897	Remote Similarity	NPD7703	Clinical (unspecified phase)
0.6892	Remote Similarity	NPD8101	Phase 3
0.6885	Remote Similarity	NPD7807	Clinical (unspecified phase)
0.6883	Remote Similarity	NPD7417	Discontinued
0.6878	Remote Similarity	NPD6242	Discontinued
0.6875	Remote Similarity	NPD5640	Discontinued
0.687	Remote Similarity	NPD5429	Discontinued
0.6866	Remote Similarity	NPD7414	Clinical (unspecified phase)
0.686	Remote Similarity	NPD5022	Discontinued
0.686	Remote Similarity	NPD5801	Clinical (unspecified phase)
0.6856	Remote Similarity	NPD3946	Clinical (unspecified phase)
0.6855	Remote Similarity	NPD6716	Phase 1
0.6849	Remote Similarity	NPD4923	Phase 1
0.6844	Remote Similarity	NPD4373	Phase 2
0.6842	Remote Similarity	NPD2921	Clinical (unspecified phase)
0.684	Remote Similarity	NPD2510	Approved
0.684	Remote Similarity	NPD6460	Clinical (unspecified phase)
0.684	Remote Similarity	NPD2509	Approved
0.6836	Remote Similarity	NPD7956	Approved
0.6836	Remote Similarity	NPD7955	Approved
0.6835	Remote Similarity	NPD6955	Clinical (unspecified phase)
0.6828	Remote Similarity	NPD4396	Clinical (unspecified phase)
0.6812	Remote Similarity	NPD5513	Phase 2
0.6809	Remote Similarity	NPD6530	Approved
0.6809	Remote Similarity	NPD6531	Approved
0.68	Remote Similarity	NPD6550	Discontinued
0.68	Remote Similarity	NPD5512	Phase 3
0.6795	Remote Similarity	NPD3816	Phase 1
0.6795	Remote Similarity	NPD3815	Phase 1
0.6789	Remote Similarity	NPD3386	Phase 2
0.6784	Remote Similarity	NPD6874	Approved
0.6783	Remote Similarity	NPD7862	Clinical (unspecified phase)
0.678	Remote Similarity	NPD3394	Approved
0.678	Remote Similarity	NPD3389	Approved
0.678	Remote Similarity	NPD3393	Approved
0.6778	Remote Similarity	NPD5147	Discontinued
0.6769	Remote Similarity	NPD5450	Discontinued
0.6762	Remote Similarity	NPD6962	Phase 2
0.6761	Remote Similarity	NPD6872	Clinical (unspecified phase)
0.6757	Remote Similarity	NPD7234	Approved
0.6757	Remote Similarity	NPD7233	Approved
0.6747	Remote Similarity	NPD6790	Phase 1
0.6745	Remote Similarity	NPD4926	Clinical (unspecified phase)
0.6742	Remote Similarity	NPD4375	Approved
0.6741	Remote Similarity	NPD6569	Phase 2
0.6737	Remote Similarity	NPD7538	Clinical (unspecified phase)
0.6735	Remote Similarity	NPD5015	Clinical (unspecified phase)
0.6732	Remote Similarity	NPD8091	Phase 3
0.6729	Remote Similarity	NPD3217	Phase 2
0.6728	Remote Similarity	NPD5751	Clinical (unspecified phase)
0.6726	Remote Similarity	NPD3478	Clinical (unspecified phase)
0.6726	Remote Similarity	NPD3477	Phase 2
0.6723	Remote Similarity	NPD5632	Approved
0.6723	Remote Similarity	NPD4429	Discontinued
0.6708	Remote Similarity	NPD7994	Phase 2
0.6707	Remote Similarity	NPD6741	Clinical (unspecified phase)
0.6699	Remote Similarity	NPD6026	Approved
0.6698	Remote Similarity	NPD5088	Discontinued
0.6681	Remote Similarity	NPD5601	Phase 2
0.6681	Remote Similarity	NPD4107	Approved
0.6667	Remote Similarity	NPD4667	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD7426	Phase 1
0.6653	Remote Similarity	NPD1659	Phase 1
0.6652	Remote Similarity	NPD4081	Clinical (unspecified phase)
0.6651	Remote Similarity	NPD1032	Phase 2
0.6639	Remote Similarity	NPD6298	Discontinued
0.6639	Remote Similarity	NPD7826	Clinical (unspecified phase)
0.6638	Remote Similarity	NPD31	Approved
0.6638	Remote Similarity	NPD4122	Approved
0.6638	Remote Similarity	NPD4037	Approved
0.6638	Remote Similarity	NPD4036	Approved
0.6638	Remote Similarity	NPD4039	Approved
0.6638	Remote Similarity	NPD4034	Approved
0.6638	Remote Similarity	NPD4038	Approved
0.6638	Remote Similarity	NPD5914	Approved
0.6638	Remote Similarity	NPD4033	Approved
0.6638	Remote Similarity	NPD32	Approved
0.6638	Remote Similarity	NPD4035	Approved
0.6637	Remote Similarity	NPD4551	Phase 2
0.6636	Remote Similarity	NPD1923	Clinical (unspecified phase)
0.6627	Remote Similarity	NPD5805	Approved
0.6626	Remote Similarity	NPD6247	Clinical (unspecified phase)
0.6625	Remote Similarity	NPD3763	Approved
0.6625	Remote Similarity	NPD6974	Phase 3
0.6623	Remote Similarity	NPD7238	Clinical (unspecified phase)
0.6621	Remote Similarity	NPD1620	Clinical (unspecified phase)
0.662	Remote Similarity	NPD1078	Clinical (unspecified phase)
0.6617	Remote Similarity	NPD7053	Clinical (unspecified phase)
0.6608	Remote Similarity	NPD5975	Clinical (unspecified phase)
0.6608	Remote Similarity	NPD4418	Discontinued
0.6601	Remote Similarity	NPD7967	Discontinued
0.66	Remote Similarity	NPD7660	Clinical (unspecified phase)
0.6598	Remote Similarity	NPD3263	Phase 3
0.6597	Remote Similarity	NPD7707	Approved
0.6597	Remote Similarity	NPD5149	Phase 2
0.6597	Remote Similarity	NPD5293	Phase 2
0.6597	Remote Similarity	NPD5148	Clinical (unspecified phase)
0.6595	Remote Similarity	NPD2121	Clinical (unspecified phase)
0.6592	Remote Similarity	NPD4919	Phase 3
0.6592	Remote Similarity	NPD4921	Phase 3
0.6592	Remote Similarity	NPD4920	Clinical (unspecified phase)
0.6591	Remote Similarity	NPD7393	Clinical (unspecified phase)
0.6588	Remote Similarity	NPD8102	Discontinued
0.6587	Remote Similarity	NPD5883	Phase 2
0.6586	Remote Similarity	NPD5891	Approved
0.6586	Remote Similarity	NPD7853	Phase 2
0.6585	Remote Similarity	NPD5479	Discontinued
0.6584	Remote Similarity	NPD7278	Phase 2
0.6584	Remote Similarity	NPD7547	Clinical (unspecified phase)
0.6584	Remote Similarity	NPD7279	Phase 2
0.6583	Remote Similarity	NPD1926	Approved
0.6583	Remote Similarity	NPD3354	Phase 2
0.658	Remote Similarity	NPD4482	Phase 3
0.6573	Remote Similarity	NPD6494	Phase 2
0.6573	Remote Similarity	NPD7558	Phase 2
0.6571	Remote Similarity	NPD6553	Clinical (unspecified phase)
0.6567	Remote Similarity	NPD3947	Discontinued
0.6567	Remote Similarity	NPD7396	Approved
0.6562	Remote Similarity	NPD6475	Phase 2
0.6555	Remote Similarity	NPD3795	Approved
0.6555	Remote Similarity	NPD3794	Approved
0.6553	Remote Similarity	NPD4642	Clinical (unspecified phase)
0.6552	Remote Similarity	NPD5867	Clinical (unspecified phase)
0.6552	Remote Similarity	NPD6228	Discontinued
0.6549	Remote Similarity	NPD2334	Discontinued
0.6549	Remote Similarity	NPD6276	Discontinued
0.6549	Remote Similarity	NPD8358	Approved
0.6546	Remote Similarity	NPD4333	Phase 1
0.6546	Remote Similarity	NPD6963	Approved
0.6546	Remote Similarity	NPD6964	Approved
0.6543	Remote Similarity	NPD6824	Clinical (unspecified phase)
0.6543	Remote Similarity	NPD8356	Approved
0.6542	Remote Similarity	NPD8404	Phase 2
0.654	Remote Similarity	NPD5416	Discontinued
0.6535	Remote Similarity	NPD3396	Approved
0.6535	Remote Similarity	NPD7792	Phase 1
0.6535	Remote Similarity	NPD3395	Approved
0.6533	Remote Similarity	NPD4021	Phase 2
0.6529	Remote Similarity	NPD7180	Phase 3
0.652	Remote Similarity	NPD4372	Phase 1
0.6509	Remote Similarity	NPD820	Phase 3
0.65	Remote Similarity	NPD4072	Approved
0.65	Remote Similarity	NPD4071	Approved
0.6494	Remote Similarity	NPD2778	Approved
0.649	Remote Similarity	NPD3925	Approved
0.6489	Remote Similarity	NPD1033	Clinical (unspecified phase)
0.6489	Remote Similarity	NPD1034	Phase 3
0.6485	Remote Similarity	NPD3945	Discontinued
0.6481	Remote Similarity	NPD7123	Suspended
0.6478	Remote Similarity	NPD6759	Phase 2
0.6475	Remote Similarity	NPD6160	Clinical (unspecified phase)
0.6473	Remote Similarity	NPD8327	Clinical (unspecified phase)
0.6473	Remote Similarity	NPD8325	Phase 3
0.6473	Remote Similarity	NPD8326	Phase 3
0.6471	Remote Similarity	NPD6567	Clinical (unspecified phase)
0.6471	Remote Similarity	NPD3920	Phase 2
0.6468	Remote Similarity	NPD6727	Phase 2
0.6468	Remote Similarity	NPD6245	Phase 2
0.6466	Remote Similarity	NPD4491	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