NPASS Compound

Structure

NPC472442 OpenBabel07101718322D 30 32 0 0 1 0 0 0 0 0999 V2000 -5.9868 -3.2742 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1208 1.2258 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1880 4.5222 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1894 4.4698 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6250 3.1772 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.9868 -2.2742 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3853 0.7173 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3887 -2.7742 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2548 -3.2742 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3887 -1.7742 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.9868 -0.2742 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5817 0.1741 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.9868 -1.2742 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2888 -0.5330 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2574 -1.0183 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1208 -2.7742 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1208 0.2258 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.6158 -0.0847 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2548 -1.2742 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.2588 -0.9659 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8387 0.5446 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -0.0523 2.0879 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7340 3.6312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1208 -1.7742 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.2548 -0.2742 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.3705 -1.7431 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8387 1.6339 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 -0.8910 1.5433 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.1047 3.0865 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 16 1 0 0 0 0 2 17 1 0 0 0 0 3 23 1 0 0 0 0 4 23 1 0 0 0 0 5 23 1 0 0 0 0 8 9 1 0 0 0 0 8 10 1 0 0 0 0 9 16 2 0 0 0 0 10 19 1 0 0 0 0 11 13 1 0 0 0 0 11 17 1 0 0 0 0 12 14 1 0 0 0 0 12 18 1 0 0 0 0 13 24 1 0 0 0 0 14 25 1 0 0 0 0 15 18 2 0 0 0 0 15 20 1 0 0 0 0 16 24 1 0 0 0 0 17 25 1 1 0 0 0 18 21 1 0 0 0 0 19 24 1 1 0 0 0 19 25 1 0 0 0 0 20 26 2 0 0 0 0 20 28 1 0 0 0 0 21 28 1 0 0 0 0 21 29 1 0 0 0 0 22 27 2 0 0 0 0 22 29 1 0 0 0 0 22 30 1 0 0 0 0 23 30 1 0 0 0 0 24 6 1 1 0 0 0 25 7 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	418.27
Volume:	448.692
LogP:	5.798
LogD:	4.994
LogS:	-5.601
# Rotatable Bonds:	7
TPSA:	68.9
# H-Bond Aceptor:	5
# H-Bond Donor:	1
# Rings:	3
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.42
Synthetic Accessibility Score:	4.566
Fsp3:	0.72
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:	-4.812
MDCK Permeability:	2.79582709481474e-05
Pgp-inhibitor:	0.361
Pgp-substrate:	0.002
Human Intestinal Absorption (HIA):	0.008
20% Bioavailability (F20%):	0.065
30% Bioavailability (F30%):	0.757

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.487
Plasma Protein Binding (PPB):	98.24109649658203%
Volume Distribution (VD):	1.216
Pgp-substrate:	3.12500262260437%

ADMET: Metabolism

CYP1A2-inhibitor:	0.102
CYP1A2-substrate:	0.264
CYP2C19-inhibitor:	0.376
CYP2C19-substrate:	0.857
CYP2C9-inhibitor:	0.334
CYP2C9-substrate:	0.885
CYP2D6-inhibitor:	0.091
CYP2D6-substrate:	0.608
CYP3A4-inhibitor:	0.419
CYP3A4-substrate:	0.209

ADMET: Excretion

Clearance (CL):	11.481
Half-life (T1/2):	0.687

ADMET: Toxicity

hERG Blockers:	0.0
Human Hepatotoxicity (H-HT):	0.046
Drug-inuced Liver Injury (DILI):	0.084
AMES Toxicity:	0.005
Rat Oral Acute Toxicity:	0.067
Maximum Recommended Daily Dose:	0.083
Skin Sensitization:	0.877
Carcinogencity:	0.133
Eye Corrosion:	0.588
Eye Irritation:	0.374
Respiratory Toxicity:	0.965

Download Data

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

Natural Product: NPC472442

Natural Product ID:	NPC472442
*Common Name:**	UJVJNBBSPRJHGY-NXXIYKHGSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	UJVJNBBSPRJHGY-NXXIYKHGSA-N
Standard InCHI:	InChI=1S/C25H38O5/c1-16-9-8-10-19-24(16,6)13-11-17(2)25(19,7)14-12-18-15-20(26)28-21(18)29-22(27)30-23(3,4)5/h9,15,17,19,21H,8,10-14H2,1-7H3/t17-,19+,21?,24+,25+/m1/s1
SMILES:	O=C(OC(C)(C)C)OC1OC(=O)C=C1CC[C@@]1(C)[C@H](C)CC[C@@]2([C@@H]1CCC=C2C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3415666
PubChem CID:	n.a.
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001283] Terpene lactones [CHEMONTID:0001538] Diterpene lactones

*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
NPO30067.1	Polyalthia longifolia var. pendula	Varieties	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11087586]
NPO30067.1	Polyalthia longifolia var. pendula	Varieties	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19860383]
NPO30067.1	Polyalthia longifolia var. pendula	Varieties	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25747495]
NPO30067.1	Polyalthia longifolia var. pendula	Varieties	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]

☑ 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
Others	10

Activity Type	# Activity
Organism	9
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT20	Organism	Candida albicans	Candida albicans	Activity	=	153.1	uM	PMID[545019]
NPT27	Others	Unspecified		Activity	<	15.0	%	PMID[545019]
NPT3644	Organism	Neurospora crassa	Neurospora crassa	MIC90	>	600000.0	nM	PMID[545019]
NPT637	Organism	Fusarium oxysporum	Fusarium oxysporum	MIC90	>	600000.0	nM	PMID[545019]
NPT21	Organism	Aspergillus niger	Aspergillus niger	MIC90	>	600000.0	nM	PMID[545019]
NPT87	Organism	Aspergillus fumigatus	Aspergillus fumigatus	MIC90	>	600000.0	nM	PMID[545019]
NPT85	Organism	Filobasidiella neoformans	Cryptococcus neoformans	MIC90	>	600000.0	nM	PMID[545019]
NPT554	Organism	Candida glabrata	Candida glabrata	MIC90	>	600000.0	nM	PMID[545019]
NPT20	Organism	Candida albicans	Candida albicans	MIC90	>	600000.0	nM	PMID[545019]

☑ 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 NPC472442 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	192
0.1-0.2	1386
0.2-0.3	5493
0.3-0.4	14984
0.4-0.5	8918
0.5-0.6	7522
0.6-0.7	3495
0.7-0.8	657
0.8-0.85	37
0.85-0.9	11
0.9-0.95	0
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9747	High Similarity	NPC472440
0.8837	High Similarity	NPC470734
0.881	High Similarity	NPC42586
0.881	High Similarity	NPC473251
0.869	High Similarity	NPC71626
0.8675	High Similarity	NPC471218
0.8652	High Similarity	NPC298973
0.8652	High Similarity	NPC104925
0.8652	High Similarity	NPC477722
0.8636	High Similarity	NPC477122
0.8621	High Similarity	NPC293044
0.8571	High Similarity	NPC477124
0.8506	High Similarity	NPC472810
0.8506	High Similarity	NPC472809
0.8488	Intermediate Similarity	NPC118266
0.8481	Intermediate Similarity	NPC476489
0.8481	Intermediate Similarity	NPC476490
0.8471	Intermediate Similarity	NPC471302
0.8471	Intermediate Similarity	NPC471301
0.8444	Intermediate Similarity	NPC469697
0.8427	Intermediate Similarity	NPC65513
0.8372	Intermediate Similarity	NPC189311
0.8372	Intermediate Similarity	NPC474013
0.8352	Intermediate Similarity	NPC472441
0.8295	Intermediate Similarity	NPC474629
0.8295	Intermediate Similarity	NPC93411
0.8276	Intermediate Similarity	NPC471219
0.8261	Intermediate Similarity	NPC319692
0.8261	Intermediate Similarity	NPC325960
0.8261	Intermediate Similarity	NPC162346
0.8261	Intermediate Similarity	NPC112654
0.8256	Intermediate Similarity	NPC318515
0.8242	Intermediate Similarity	NPC324078
0.8242	Intermediate Similarity	NPC88507
0.8235	Intermediate Similarity	NPC471298
0.8222	Intermediate Similarity	NPC329842
0.8222	Intermediate Similarity	NPC472811
0.8214	Intermediate Similarity	NPC473685
0.8191	Intermediate Similarity	NPC477721
0.8191	Intermediate Similarity	NPC324841
0.8191	Intermediate Similarity	NPC477716
0.8172	Intermediate Similarity	NPC477719
0.8172	Intermediate Similarity	NPC257726
0.8172	Intermediate Similarity	NPC477718
0.8172	Intermediate Similarity	NPC204054
0.8152	Intermediate Similarity	NPC471372
0.8152	Intermediate Similarity	NPC472189
0.8152	Intermediate Similarity	NPC471362
0.814	Intermediate Similarity	NPC30502
0.814	Intermediate Similarity	NPC324243
0.814	Intermediate Similarity	NPC471297
0.814	Intermediate Similarity	NPC474193
0.814	Intermediate Similarity	NPC12283
0.8132	Intermediate Similarity	NPC472812
0.8125	Intermediate Similarity	NPC120009
0.8111	Intermediate Similarity	NPC477782
0.8105	Intermediate Similarity	NPC477717
0.8095	Intermediate Similarity	NPC242767
0.809	Intermediate Similarity	NPC472378
0.809	Intermediate Similarity	NPC196407
0.809	Intermediate Similarity	NPC226863
0.8065	Intermediate Similarity	NPC94905
0.8065	Intermediate Similarity	NPC171598
0.8065	Intermediate Similarity	NPC311166
0.8065	Intermediate Similarity	NPC8954
0.8046	Intermediate Similarity	NPC96055
0.8043	Intermediate Similarity	NPC470255
0.8043	Intermediate Similarity	NPC474554
0.8023	Intermediate Similarity	NPC256112
0.8023	Intermediate Similarity	NPC200513
0.8022	Intermediate Similarity	NPC141831
0.8022	Intermediate Similarity	NPC179517
0.8022	Intermediate Similarity	NPC165904
0.8022	Intermediate Similarity	NPC477783
0.8	Intermediate Similarity	NPC177141
0.8	Intermediate Similarity	NPC233332
0.8	Intermediate Similarity	NPC251528
0.8	Intermediate Similarity	NPC5509
0.7979	Intermediate Similarity	NPC476768
0.7979	Intermediate Similarity	NPC98112
0.7979	Intermediate Similarity	NPC472188
0.7975	Intermediate Similarity	NPC476945
0.7959	Intermediate Similarity	NPC127790
0.7957	Intermediate Similarity	NPC473369
0.7955	Intermediate Similarity	NPC30984
0.7955	Intermediate Similarity	NPC163606
0.7938	Intermediate Similarity	NPC132395
0.7938	Intermediate Similarity	NPC471365
0.7938	Intermediate Similarity	NPC471364
0.7935	Intermediate Similarity	NPC7349
0.7931	Intermediate Similarity	NPC193198
0.7931	Intermediate Similarity	NPC311070
0.7931	Intermediate Similarity	NPC476927
0.7931	Intermediate Similarity	NPC469
0.7912	Intermediate Similarity	NPC281942
0.7912	Intermediate Similarity	NPC232426
0.7912	Intermediate Similarity	NPC469403
0.7912	Intermediate Similarity	NPC78973
0.7907	Intermediate Similarity	NPC25554
0.7895	Intermediate Similarity	NPC474440
0.7895	Intermediate Similarity	NPC471366
0.7895	Intermediate Similarity	NPC472186
0.7895	Intermediate Similarity	NPC476800
0.7895	Intermediate Similarity	NPC318917
0.7895	Intermediate Similarity	NPC473154
0.7889	Intermediate Similarity	NPC106332
0.7889	Intermediate Similarity	NPC472302
0.7872	Intermediate Similarity	NPC73858
0.7872	Intermediate Similarity	NPC240673
0.7872	Intermediate Similarity	NPC17578
0.7865	Intermediate Similarity	NPC131813
0.7865	Intermediate Similarity	NPC474062
0.7865	Intermediate Similarity	NPC220478
0.7857	Intermediate Similarity	NPC316500
0.7857	Intermediate Similarity	NPC54996
0.7857	Intermediate Similarity	NPC473756
0.7857	Intermediate Similarity	NPC189206
0.7857	Intermediate Similarity	NPC476763
0.7857	Intermediate Similarity	NPC476764
0.7849	Intermediate Similarity	NPC105490
0.7849	Intermediate Similarity	NPC304968
0.7849	Intermediate Similarity	NPC140277
0.7849	Intermediate Similarity	NPC128488
0.7841	Intermediate Similarity	NPC126518
0.7841	Intermediate Similarity	NPC470800
0.7835	Intermediate Similarity	NPC134077
0.7835	Intermediate Similarity	NPC472815
0.7816	Intermediate Similarity	NPC323251
0.7812	Intermediate Similarity	NPC473204
0.7812	Intermediate Similarity	NPC477720
0.7812	Intermediate Similarity	NPC472187
0.7812	Intermediate Similarity	NPC473545
0.7805	Intermediate Similarity	NPC16349
0.7805	Intermediate Similarity	NPC222244
0.7802	Intermediate Similarity	NPC284561
0.7802	Intermediate Similarity	NPC174342
0.7791	Intermediate Similarity	NPC268827
0.7791	Intermediate Similarity	NPC469802
0.7789	Intermediate Similarity	NPC309503
0.7789	Intermediate Similarity	NPC475709
0.7789	Intermediate Similarity	NPC96597
0.7789	Intermediate Similarity	NPC125551
0.7789	Intermediate Similarity	NPC91197
0.7789	Intermediate Similarity	NPC239547
0.7789	Intermediate Similarity	NPC155319
0.7778	Intermediate Similarity	NPC476762
0.7778	Intermediate Similarity	NPC476600
0.7778	Intermediate Similarity	NPC476761
0.7778	Intermediate Similarity	NPC166857
0.7778	Intermediate Similarity	NPC172867
0.7778	Intermediate Similarity	NPC476760
0.7766	Intermediate Similarity	NPC276110
0.7765	Intermediate Similarity	NPC184737
0.7755	Intermediate Similarity	NPC45897
0.7753	Intermediate Similarity	NPC329630
0.7753	Intermediate Similarity	NPC65661
0.7753	Intermediate Similarity	NPC471795
0.7742	Intermediate Similarity	NPC166346
0.7742	Intermediate Similarity	NPC472303
0.7742	Intermediate Similarity	NPC471571
0.7742	Intermediate Similarity	NPC475657
0.7732	Intermediate Similarity	NPC63249
0.7727	Intermediate Similarity	NPC49208
0.7727	Intermediate Similarity	NPC22611
0.7727	Intermediate Similarity	NPC42476
0.7727	Intermediate Similarity	NPC23748
0.7727	Intermediate Similarity	NPC474809
0.7723	Intermediate Similarity	NPC206618
0.7717	Intermediate Similarity	NPC469595
0.7717	Intermediate Similarity	NPC273199
0.7717	Intermediate Similarity	NPC212679
0.7717	Intermediate Similarity	NPC220454
0.7717	Intermediate Similarity	NPC302280
0.7701	Intermediate Similarity	NPC282293
0.7701	Intermediate Similarity	NPC170303
0.77	Intermediate Similarity	NPC475074
0.77	Intermediate Similarity	NPC109376
0.7692	Intermediate Similarity	NPC144069
0.7684	Intermediate Similarity	NPC209297
0.7684	Intermediate Similarity	NPC475380
0.7684	Intermediate Similarity	NPC470801
0.7684	Intermediate Similarity	NPC194132
0.7674	Intermediate Similarity	NPC17550
0.7667	Intermediate Similarity	NPC286153
0.7667	Intermediate Similarity	NPC173917
0.766	Intermediate Similarity	NPC120351
0.766	Intermediate Similarity	NPC475572
0.766	Intermediate Similarity	NPC474555
0.766	Intermediate Similarity	NPC166143
0.766	Intermediate Similarity	NPC471994
0.7653	Intermediate Similarity	NPC476769
0.7653	Intermediate Similarity	NPC471363
0.7653	Intermediate Similarity	NPC471993
0.7653	Intermediate Similarity	NPC238397
0.764	Intermediate Similarity	NPC30486
0.764	Intermediate Similarity	NPC306951
0.764	Intermediate Similarity	NPC149869
0.7634	Intermediate Similarity	NPC289479
0.7634	Intermediate Similarity	NPC177641
0.7629	Intermediate Similarity	NPC477971

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 NPC472442 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	167
0.1-0.2	1657
0.2-0.3	4191
0.3-0.4	2215
0.4-0.5	550
0.5-0.6	280
0.6-0.7	84
0.7-0.8	6
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
0.8023	Intermediate Similarity	NPD4752	Clinical (unspecified phase)
0.7841	Intermediate Similarity	NPD6400	Clinical (unspecified phase)
0.7802	Intermediate Similarity	NPD6051	Approved
0.7451	Intermediate Similarity	NPD6686	Approved
0.7312	Intermediate Similarity	NPD6672	Approved
0.7312	Intermediate Similarity	NPD5737	Approved
0.7283	Intermediate Similarity	NPD7146	Approved
0.7283	Intermediate Similarity	NPD7521	Approved
0.7283	Intermediate Similarity	NPD7334	Approved
0.7283	Intermediate Similarity	NPD6684	Approved
0.7283	Intermediate Similarity	NPD6409	Approved
0.7283	Intermediate Similarity	NPD5330	Approved
0.7263	Intermediate Similarity	NPD5693	Phase 1
0.7174	Intermediate Similarity	NPD1694	Approved
0.7172	Intermediate Similarity	NPD7638	Approved
0.7156	Intermediate Similarity	NPD7328	Approved
0.7156	Intermediate Similarity	NPD7327	Approved
0.7128	Intermediate Similarity	NPD6903	Approved
0.7128	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.71	Intermediate Similarity	NPD7639	Approved
0.71	Intermediate Similarity	NPD7640	Approved
0.7091	Intermediate Similarity	NPD7516	Approved
0.7053	Intermediate Similarity	NPD6904	Approved
0.7053	Intermediate Similarity	NPD6080	Approved
0.7053	Intermediate Similarity	NPD6673	Approved
0.7027	Intermediate Similarity	NPD8377	Approved
0.7027	Intermediate Similarity	NPD8294	Approved
0.6964	Remote Similarity	NPD7503	Approved
0.6964	Remote Similarity	NPD8380	Approved
0.6964	Remote Similarity	NPD8379	Approved
0.6964	Remote Similarity	NPD8296	Approved
0.6964	Remote Similarity	NPD8033	Approved
0.6964	Remote Similarity	NPD8378	Approved
0.6964	Remote Similarity	NPD8335	Approved
0.6951	Remote Similarity	NPD2685	Clinical (unspecified phase)
0.6907	Remote Similarity	NPD6050	Approved
0.69	Remote Similarity	NPD6084	Phase 2
0.69	Remote Similarity	NPD6083	Phase 2
0.6869	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6869	Remote Similarity	NPD5695	Phase 3
0.6832	Remote Similarity	NPD4225	Approved
0.6829	Remote Similarity	NPD5325	Clinical (unspecified phase)
0.6818	Remote Similarity	NPD8039	Approved
0.6804	Remote Similarity	NPD5692	Phase 3
0.6771	Remote Similarity	NPD5208	Approved
0.6768	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6768	Remote Similarity	NPD7900	Approved
0.6768	Remote Similarity	NPD7748	Approved
0.6737	Remote Similarity	NPD6098	Approved
0.6735	Remote Similarity	NPD5694	Approved
0.6724	Remote Similarity	NPD7507	Approved
0.6698	Remote Similarity	NPD6412	Phase 2
0.6667	Remote Similarity	NPD5696	Approved
0.6667	Remote Similarity	NPD6399	Phase 3
0.6667	Remote Similarity	NPD3573	Approved
0.6633	Remote Similarity	NPD5207	Approved
0.6569	Remote Similarity	NPD7902	Approved
0.6566	Remote Similarity	NPD7515	Phase 2
0.6555	Remote Similarity	NPD7319	Approved
0.6545	Remote Similarity	NPD6882	Approved
0.6542	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6522	Remote Similarity	NPD4195	Approved
0.6489	Remote Similarity	NPD5209	Approved
0.6476	Remote Similarity	NPD7632	Discontinued
0.646	Remote Similarity	NPD7115	Discovery
0.6449	Remote Similarity	NPD6675	Approved
0.6449	Remote Similarity	NPD7128	Approved
0.6449	Remote Similarity	NPD6402	Approved
0.6449	Remote Similarity	NPD5739	Approved
0.6436	Remote Similarity	NPD6001	Approved
0.6422	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.64	Remote Similarity	NPD5281	Approved
0.64	Remote Similarity	NPD5284	Approved
0.6392	Remote Similarity	NPD4623	Approved
0.6392	Remote Similarity	NPD4519	Discontinued
0.6373	Remote Similarity	NPD5654	Approved
0.6364	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD4753	Phase 2
0.6354	Remote Similarity	NPD3666	Approved
0.6354	Remote Similarity	NPD3133	Approved
0.6354	Remote Similarity	NPD3665	Phase 1
0.6346	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.633	Remote Similarity	NPD7320	Approved
0.633	Remote Similarity	NPD6899	Approved
0.633	Remote Similarity	NPD6881	Approved
0.6316	Remote Similarity	NPD4221	Approved
0.6316	Remote Similarity	NPD4223	Phase 3
0.6296	Remote Similarity	NPD6008	Approved
0.6292	Remote Similarity	NPD4243	Approved
0.6289	Remote Similarity	NPD5329	Approved
0.6286	Remote Similarity	NPD6648	Approved
0.6277	Remote Similarity	NPD7525	Registered
0.6273	Remote Similarity	NPD6373	Approved
0.6273	Remote Similarity	NPD6372	Approved
0.6265	Remote Similarity	NPD1145	Discontinued
0.6264	Remote Similarity	NPD6942	Approved
0.6264	Remote Similarity	NPD7339	Approved
0.6262	Remote Similarity	NPD6052	Approved
0.625	Remote Similarity	NPD6695	Phase 3
0.625	Remote Similarity	NPD6053	Discontinued
0.625	Remote Similarity	NPD5959	Approved
0.6239	Remote Similarity	NPD5701	Approved
0.6239	Remote Similarity	NPD5697	Approved
0.6238	Remote Similarity	NPD7637	Suspended
0.6226	Remote Similarity	NPD5344	Discontinued
0.6224	Remote Similarity	NPD3618	Phase 1
0.6216	Remote Similarity	NPD6883	Approved
0.6216	Remote Similarity	NPD7102	Approved
0.6216	Remote Similarity	NPD7290	Approved
0.62	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.62	Remote Similarity	NPD5328	Approved
0.6196	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.6195	Remote Similarity	NPD8133	Approved
0.6186	Remote Similarity	NPD3668	Phase 3
0.6186	Remote Similarity	NPD4197	Approved
0.6186	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6186	Remote Similarity	NPD4786	Approved
0.6182	Remote Similarity	NPD6011	Approved
0.617	Remote Similarity	NPD7645	Phase 2
0.6161	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6161	Remote Similarity	NPD6650	Approved
0.6161	Remote Similarity	NPD6617	Approved
0.6161	Remote Similarity	NPD6649	Approved
0.6161	Remote Similarity	NPD6869	Approved
0.6161	Remote Similarity	NPD6847	Approved
0.6161	Remote Similarity	NPD8130	Phase 1
0.6154	Remote Similarity	NPD6924	Approved
0.6154	Remote Similarity	NPD7732	Phase 3
0.6154	Remote Similarity	NPD4784	Approved
0.6154	Remote Similarity	NPD4785	Approved
0.6154	Remote Similarity	NPD6926	Approved
0.6146	Remote Similarity	NPD3667	Approved
0.6139	Remote Similarity	NPD5785	Approved
0.6126	Remote Similarity	NPD6014	Approved
0.6126	Remote Similarity	NPD6013	Approved
0.6126	Remote Similarity	NPD6012	Approved
0.6122	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6117	Remote Similarity	NPD5707	Approved
0.6116	Remote Similarity	NPD8293	Discontinued
0.6106	Remote Similarity	NPD8297	Approved
0.6105	Remote Similarity	NPD4695	Discontinued
0.6091	Remote Similarity	NPD6614	Approved
0.6078	Remote Similarity	NPD6411	Approved
0.6078	Remote Similarity	NPD6079	Approved
0.6067	Remote Similarity	NPD4137	Phase 3
0.6066	Remote Similarity	NPD7736	Approved
0.6061	Remote Similarity	NPD5690	Phase 2
0.6061	Remote Similarity	NPD4690	Approved
0.6061	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6061	Remote Similarity	NPD4138	Approved
0.6061	Remote Similarity	NPD4693	Phase 3
0.6061	Remote Similarity	NPD4689	Approved
0.6061	Remote Similarity	NPD5205	Approved
0.6061	Remote Similarity	NPD4694	Approved
0.6061	Remote Similarity	NPD4688	Approved
0.6061	Remote Similarity	NPD5279	Phase 3
0.6061	Remote Similarity	NPD5280	Approved
0.6058	Remote Similarity	NPD5210	Approved
0.6058	Remote Similarity	NPD4629	Approved
0.605	Remote Similarity	NPD6370	Approved
0.6034	Remote Similarity	NPD6009	Approved
0.6022	Remote Similarity	NPD6933	Approved
0.6019	Remote Similarity	NPD4202	Approved
0.6019	Remote Similarity	NPD5779	Approved
0.6019	Remote Similarity	NPD5778	Approved
0.6	Remote Similarity	NPD4192	Approved
0.6	Remote Similarity	NPD4751	Clinical (unspecified phase)
0.6	Remote Similarity	NPD7750	Discontinued
0.6	Remote Similarity	NPD4194	Approved
0.6	Remote Similarity	NPD4691	Approved
0.6	Remote Similarity	NPD4193	Approved
0.6	Remote Similarity	NPD7524	Approved
0.6	Remote Similarity	NPD4747	Approved
0.6	Remote Similarity	NPD8328	Phase 3
0.6	Remote Similarity	NPD4191	Approved
0.5982	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.5981	Remote Similarity	NPD6404	Discontinued
0.598	Remote Similarity	NPD6698	Approved
0.598	Remote Similarity	NPD7838	Discovery
0.598	Remote Similarity	NPD46	Approved
0.5978	Remote Similarity	NPD5733	Approved
0.5968	Remote Similarity	NPD6914	Discontinued
0.595	Remote Similarity	NPD7492	Approved
0.5943	Remote Similarity	NPD4755	Approved
0.5938	Remote Similarity	NPD6931	Approved
0.5938	Remote Similarity	NPD6930	Phase 2
0.5922	Remote Similarity	NPD8035	Phase 2
0.5922	Remote Similarity	NPD8034	Phase 2
0.5914	Remote Similarity	NPD8264	Approved
0.5914	Remote Similarity	NPD4190	Phase 3
0.5914	Remote Similarity	NPD5275	Approved
0.5905	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.5902	Remote Similarity	NPD6616	Approved
0.5895	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.5895	Remote Similarity	NPD7322	Clinical (unspecified phase)
0.5895	Remote Similarity	NPD3617	Approved
0.5882	Remote Similarity	NPD6101	Approved
0.5882	Remote Similarity	NPD6059	Approved
0.5882	Remote Similarity	NPD6054	Approved
0.5882	Remote Similarity	NPD5764	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