NPASS Compound

Structure

NPC20533 OpenBabel07101719402D 45 47 0 0 1 0 0 0 0 0999 V2000 19.3506 3.5146 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0933 -1.7796 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 18.5416 4.1023 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 17.6280 3.6956 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 17.5235 2.7011 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5589 3.3784 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6453 2.9716 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.6634 4.3729 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5408 1.9771 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.5769 4.7796 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6272 1.5704 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 16.6099 2.2944 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.6815 5.7742 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 13.8693 1.0741 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5227 0.5759 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 16.5054 1.2998 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.5950 6.1809 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 14.7828 1.4809 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 13.7648 0.0796 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.3176 5.9999 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.1266 5.4121 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 11.0912 -0.0483 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 10.7821 4.1388 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 10.5034 0.7607 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 11.3699 3.3298 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4013 -0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4067 -0.9135 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.6092 0.1691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 15.5919 0.8931 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 7.4040 5.5931 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 12.8512 -0.3271 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 9.0221 4.4175 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 12.0422 0.2607 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 9.8311 3.8298 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 11.0912 1.5697 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 10.7821 2.5207 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.7431 0.6691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 15.4873 -0.1014 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 7.2995 4.5986 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 12.7467 -1.3216 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 8.1085 4.0108 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.6386 1.6637 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 12.0422 1.2607 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 9.8311 2.8298 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 3 1 0 0 0 0 3 4 1 0 0 0 0 4 5 1 0 0 0 0 5 12 1 0 0 0 0 6 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 13 1 0 0 0 0 11 15 1 0 0 0 0 12 16 1 0 0 0 0 13 17 1 0 0 0 0 14 18 1 0 0 0 0 14 19 1 0 0 0 0 15 28 1 0 0 0 0 16 29 1 0 0 0 0 17 30 1 0 0 0 0 18 29 1 0 0 0 0 19 31 1 0 0 0 0 20 21 1 0 0 0 0 20 30 1 0 0 0 0 21 32 1 0 0 0 0 22 24 1 0 0 0 0 22 33 1 0 0 0 0 23 25 1 0 0 0 0 23 34 1 0 0 0 0 26 27 1 0 0 0 0 26 28 2 0 0 0 0 27 2 1 6 0 0 0 27 43 1 0 0 0 0 28 37 1 0 0 0 0 29 38 1 6 0 0 0 30 39 1 6 0 0 0 31 40 1 6 0 0 0 32 41 1 6 0 0 0 33 31 1 1 0 0 0 33 44 1 0 0 0 0 34 32 1 1 0 0 0 34 45 1 0 0 0 0 35 24 1 1 0 0 0 35 36 1 0 0 0 0 35 44 1 0 0 0 0 36 25 1 6 0 0 0 36 45 1 0 0 0 0 37 42 2 0 0 0 0 37 43 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	638.48
Volume:	687.887
LogP:	7.616
LogD:	4.634
LogS:	-5.462
# Rotatable Bonds:	25
TPSA:	132.75
# H-Bond Aceptor:	8
# H-Bond Donor:	5
# Rings:	3
# Heavy Atoms:	8

MedChem Properties

QED Drug-Likeness Score:	0.07
Synthetic Accessibility Score:	4.881
Fsp3:	0.892
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.322
MDCK Permeability:	1.0609917808324099e-05
Pgp-inhibitor:	0.076
Pgp-substrate:	0.998
Human Intestinal Absorption (HIA):	0.024
20% Bioavailability (F20%):	1.0
30% Bioavailability (F30%):	0.946

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.003
Plasma Protein Binding (PPB):	95.94029998779297%
Volume Distribution (VD):	0.881
Pgp-substrate:	4.013466835021973%

ADMET: Metabolism

CYP1A2-inhibitor:	0.014
CYP1A2-substrate:	0.642
CYP2C19-inhibitor:	0.043
CYP2C19-substrate:	0.057
CYP2C9-inhibitor:	0.071
CYP2C9-substrate:	0.917
CYP2D6-inhibitor:	0.007
CYP2D6-substrate:	0.072
CYP3A4-inhibitor:	0.113
CYP3A4-substrate:	0.022

ADMET: Excretion

Clearance (CL):	7.195
Half-life (T1/2):	0.118

ADMET: Toxicity

hERG Blockers:	0.335
Human Hepatotoxicity (H-HT):	0.285
Drug-inuced Liver Injury (DILI):	0.048
AMES Toxicity:	0.02
Rat Oral Acute Toxicity:	0.226
Maximum Recommended Daily Dose:	0.833
Skin Sensitization:	0.968
Carcinogencity:	0.053
Eye Corrosion:	0.003
Eye Irritation:	0.018
Respiratory Toxicity:	0.633

Download Data

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

Natural Product: NPC20533

Natural Product ID:	NPC20533
*Common Name:**	Salzmanin
IUPAC Name:	(2S)-4-[(10R,13R)-13-[(2R,5R)-5-[(2S,5R)-5-[(1S,5S)-1,5-dihydroxyundecyl]oxolan-2-yl]oxolan-2-yl]-10,13-dihydroxytridecyl]-2-methyl-2H-furan-5-one
Synonyms:	Salzmanin
Standard InCHIKey:	PRWFLCNEESBSRN-ZETXPVFNSA-N
Standard InCHI:	InChI=1S/C37H66O8/c1-3-4-5-12-16-29(38)18-14-19-31(40)33-22-24-35(44-33)36-25-23-34(45-36)32(41)21-20-30(39)17-13-10-8-6-7-9-11-15-28-26-27(2)43-37(28)42/h26-27,29-36,38-41H,3-25H2,1-2H3/t27-,29-,30+,31-,32+,33+,34+,35-,36+/m0/s1
SMILES:	CCCCCC[C@@H](CCC[C@@H]([C@H]1CC[C@@H]([C@H]2CC[C@H]([C@@H](CC[C@@H](CCCCCCCCCC3=C[C@H](C)OC3=O)O)O)O2)O1)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL507402
PubChem CID:	44566356
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0003909] Fatty Acyls [CHEMONTID:0001334] Fatty alcohols [CHEMONTID:0002518] Annonaceous acetogenins

*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
NPO33069	annona salzmanii	Species	Annonaceae	Eukaryota	roots	n.a.	n.a.	PMID[10346951]
NPO33069	annona salzmanii	Species	Annonaceae	Eukaryota	roots	n.a.	n.a.	PMID[12828457]

☑ 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
ED50	2

Activity Type	# Activity
Cell Line	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT91	Cell Line	KB	Homo sapiens	ED50	=	0.1	10'-4 ug/ml	PMID[565716]
NPT189	Cell Line	Vero	Chlorocebus aethiops	ED50	>	0.01	ug ml-1	PMID[565716]

☑ 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 NPC20533 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	193
0.1-0.2	1493
0.2-0.3	6051
0.3-0.4	14929
0.4-0.5	10402
0.5-0.6	6839
0.6-0.7	2268
0.7-0.8	341
0.8-0.85	20
0.85-0.9	26
0.9-0.95	77
0.95-1	58

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC476583
1.0	High Similarity	NPC258068
0.9878	High Similarity	NPC473905
0.9878	High Similarity	NPC320458
0.9877	High Similarity	NPC25703
0.9877	High Similarity	NPC282815
0.9877	High Similarity	NPC132940
0.9877	High Similarity	NPC219652
0.9877	High Similarity	NPC241360
0.9877	High Similarity	NPC473840
0.9877	High Similarity	NPC293136
0.9759	High Similarity	NPC91067
0.9759	High Similarity	NPC20621
0.9759	High Similarity	NPC40066
0.9759	High Similarity	NPC473504
0.9759	High Similarity	NPC93794
0.9759	High Similarity	NPC42598
0.9759	High Similarity	NPC81778
0.9759	High Similarity	NPC318963
0.9753	High Similarity	NPC329838
0.9753	High Similarity	NPC39279
0.9753	High Similarity	NPC39167
0.9753	High Similarity	NPC77871
0.9753	High Similarity	NPC25764
0.9753	High Similarity	NPC319036
0.9753	High Similarity	NPC473156
0.9753	High Similarity	NPC9678
0.9753	High Similarity	NPC475268
0.9753	High Similarity	NPC473671
0.9753	High Similarity	NPC235809
0.9753	High Similarity	NPC329615
0.9753	High Similarity	NPC470400
0.9753	High Similarity	NPC292809
0.9753	High Similarity	NPC202055
0.9643	High Similarity	NPC239517
0.9639	High Similarity	NPC61257
0.9639	High Similarity	NPC81045
0.9639	High Similarity	NPC274446
0.9639	High Similarity	NPC169511
0.9639	High Similarity	NPC100454
0.9639	High Similarity	NPC151403
0.9639	High Similarity	NPC39754
0.9639	High Similarity	NPC191929
0.9639	High Similarity	NPC171135
0.9639	High Similarity	NPC234077
0.9639	High Similarity	NPC133730
0.9639	High Similarity	NPC242364
0.9639	High Similarity	NPC172821
0.9639	High Similarity	NPC261952
0.9639	High Similarity	NPC320569
0.9639	High Similarity	NPC287164
0.963	High Similarity	NPC156804
0.9518	High Similarity	NPC473995
0.9518	High Similarity	NPC473649
0.9518	High Similarity	NPC159750
0.9518	High Similarity	NPC470401
0.9518	High Similarity	NPC154097
0.9512	High Similarity	NPC471567
0.9512	High Similarity	NPC477013
0.9512	High Similarity	NPC120398
0.9512	High Similarity	NPC322529
0.9512	High Similarity	NPC477014
0.9405	High Similarity	NPC280621
0.9405	High Similarity	NPC233551
0.9405	High Similarity	NPC40376
0.9405	High Similarity	NPC20339
0.9405	High Similarity	NPC21208
0.9405	High Similarity	NPC89001
0.9405	High Similarity	NPC48338
0.9398	High Similarity	NPC475581
0.9398	High Similarity	NPC107717
0.9398	High Similarity	NPC240695
0.9398	High Similarity	NPC171174
0.9398	High Similarity	NPC231096
0.9398	High Similarity	NPC114694
0.9398	High Similarity	NPC134865
0.9398	High Similarity	NPC232555
0.9398	High Similarity	NPC142117
0.9398	High Similarity	NPC62118
0.9398	High Similarity	NPC103523
0.9398	High Similarity	NPC477015
0.939	High Similarity	NPC163093
0.9383	High Similarity	NPC11332
0.9383	High Similarity	NPC131002
0.9383	High Similarity	NPC145914
0.9383	High Similarity	NPC73310
0.9383	High Similarity	NPC180363
0.9383	High Similarity	NPC473780
0.9383	High Similarity	NPC473712
0.9383	High Similarity	NPC475159
0.9383	High Similarity	NPC329829
0.9383	High Similarity	NPC94875
0.9383	High Similarity	NPC65930
0.9383	High Similarity	NPC473529
0.9294	High Similarity	NPC477011
0.9294	High Similarity	NPC477016
0.9294	High Similarity	NPC477017
0.9286	High Similarity	NPC178215
0.9277	High Similarity	NPC477018
0.9277	High Similarity	NPC100921
0.9277	High Similarity	NPC82795
0.9277	High Similarity	NPC103284
0.9277	High Similarity	NPC132496
0.9277	High Similarity	NPC283085
0.9277	High Similarity	NPC107986
0.9277	High Similarity	NPC223871
0.9277	High Similarity	NPC286338
0.9277	High Similarity	NPC473478
0.9277	High Similarity	NPC473669
0.9277	High Similarity	NPC1083
0.9277	High Similarity	NPC231009
0.9277	High Similarity	NPC473651
0.9277	High Similarity	NPC66346
0.9277	High Similarity	NPC110710
0.9268	High Similarity	NPC144415
0.9268	High Similarity	NPC253801
0.9195	High Similarity	NPC473520
0.9186	High Similarity	NPC473904
0.9167	High Similarity	NPC473687
0.9167	High Similarity	NPC477010
0.9167	High Similarity	NPC308412
0.9167	High Similarity	NPC219498
0.9167	High Similarity	NPC210218
0.9167	High Similarity	NPC279267
0.9167	High Similarity	NPC204686
0.9167	High Similarity	NPC134807
0.9167	High Similarity	NPC309211
0.9167	High Similarity	NPC69082
0.9167	High Similarity	NPC134885
0.907	High Similarity	NPC139418
0.907	High Similarity	NPC14901
0.907	High Similarity	NPC280612
0.907	High Similarity	NPC130359
0.9059	High Similarity	NPC477012
0.8941	High Similarity	NPC112685
0.8941	High Similarity	NPC47937
0.8824	High Similarity	NPC182383
0.8764	High Similarity	NPC475173
0.8764	High Similarity	NPC473561
0.8764	High Similarity	NPC473723
0.8764	High Similarity	NPC473663
0.8764	High Similarity	NPC11456
0.8652	High Similarity	NPC473707
0.8152	Intermediate Similarity	NPC81419
0.8152	Intermediate Similarity	NPC179746
0.8043	Intermediate Similarity	NPC30515
0.8043	Intermediate Similarity	NPC12172
0.8043	Intermediate Similarity	NPC208886
0.7979	Intermediate Similarity	NPC36954
0.7957	Intermediate Similarity	NPC476300
0.7935	Intermediate Similarity	NPC476004
0.7935	Intermediate Similarity	NPC51004
0.7935	Intermediate Similarity	NPC473619
0.7935	Intermediate Similarity	NPC473448
0.7935	Intermediate Similarity	NPC474761
0.7927	Intermediate Similarity	NPC84038
0.7917	Intermediate Similarity	NPC187268
0.7889	Intermediate Similarity	NPC469483
0.7882	Intermediate Similarity	NPC475711
0.7865	Intermediate Similarity	NPC288471
0.7857	Intermediate Similarity	NPC86077
0.7849	Intermediate Similarity	NPC184463
0.7849	Intermediate Similarity	NPC473321
0.7831	Intermediate Similarity	NPC474705
0.7826	Intermediate Similarity	NPC307411
0.7826	Intermediate Similarity	NPC295312
0.7826	Intermediate Similarity	NPC92974
0.7816	Intermediate Similarity	NPC470147
0.7816	Intermediate Similarity	NPC133226
0.7778	Intermediate Similarity	NPC21469
0.7766	Intermediate Similarity	NPC475912
0.7766	Intermediate Similarity	NPC295204
0.7766	Intermediate Similarity	NPC273579
0.7766	Intermediate Similarity	NPC288240
0.7766	Intermediate Similarity	NPC162205
0.7742	Intermediate Similarity	NPC478003
0.7742	Intermediate Similarity	NPC478004
0.7742	Intermediate Similarity	NPC158388
0.7732	Intermediate Similarity	NPC161855
0.7732	Intermediate Similarity	NPC473326
0.7717	Intermediate Similarity	NPC58219
0.7717	Intermediate Similarity	NPC202672
0.7717	Intermediate Similarity	NPC177629
0.7708	Intermediate Similarity	NPC279621
0.7708	Intermediate Similarity	NPC476315
0.7701	Intermediate Similarity	NPC180725
0.7701	Intermediate Similarity	NPC470148
0.7701	Intermediate Similarity	NPC470149
0.7692	Intermediate Similarity	NPC164393
0.7684	Intermediate Similarity	NPC474035
0.7684	Intermediate Similarity	NPC81386
0.7674	Intermediate Similarity	NPC474026
0.7634	Intermediate Similarity	NPC473564
0.7634	Intermediate Similarity	NPC474032
0.7614	Intermediate Similarity	NPC47653
0.7609	Intermediate Similarity	NPC186148
0.7609	Intermediate Similarity	NPC160138
0.7609	Intermediate Similarity	NPC248602
0.7604	Intermediate Similarity	NPC471141
0.7604	Intermediate Similarity	NPC270013

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 NPC20533 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	174
0.1-0.2	2277
0.2-0.3	3985
0.3-0.4	1915
0.4-0.5	567
0.5-0.6	201
0.6-0.7	29
0.7-0.8	2
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
0.7935	Intermediate Similarity	NPD46	Approved
0.7935	Intermediate Similarity	NPD6698	Approved
0.7553	Intermediate Similarity	NPD7838	Discovery
0.7549	Intermediate Similarity	NPD7899	Clinical (unspecified phase)
0.7308	Intermediate Similarity	NPD6686	Approved
0.7292	Intermediate Similarity	NPD7983	Approved
0.703	Intermediate Similarity	NPD8029	Clinical (unspecified phase)
0.6852	Remote Similarity	NPD6371	Approved
0.6789	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6701	Remote Similarity	NPD4250	Approved
0.6701	Remote Similarity	NPD4251	Approved
0.6667	Remote Similarity	NPD3197	Phase 1
0.6667	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.6598	Remote Similarity	NPD4249	Approved
0.6569	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.65	Remote Similarity	NPD5785	Approved
0.6495	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6458	Remote Similarity	NPD5362	Discontinued
0.6458	Remote Similarity	NPD7154	Phase 3
0.6415	Remote Similarity	NPD5344	Discontinued
0.64	Remote Similarity	NPD1695	Approved
0.6381	Remote Similarity	NPD4225	Approved
0.6381	Remote Similarity	NPD7638	Approved
0.6354	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6344	Remote Similarity	NPD4756	Discovery
0.6333	Remote Similarity	NPD7507	Approved
0.6327	Remote Similarity	NPD5363	Approved
0.6321	Remote Similarity	NPD7640	Approved
0.6321	Remote Similarity	NPD7639	Approved
0.6316	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6306	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6283	Remote Similarity	NPD6053	Discontinued
0.6271	Remote Similarity	NPD8515	Approved
0.6271	Remote Similarity	NPD8513	Phase 3
0.6271	Remote Similarity	NPD8517	Approved
0.6271	Remote Similarity	NPD8516	Approved
0.625	Remote Similarity	NPD4247	Clinical (unspecified phase)
0.619	Remote Similarity	NPD7839	Suspended
0.6186	Remote Similarity	NPD6435	Approved
0.6179	Remote Similarity	NPD7319	Approved
0.6167	Remote Similarity	NPD7830	Approved
0.6167	Remote Similarity	NPD7829	Approved
0.6129	Remote Similarity	NPD8039	Approved
0.6122	Remote Similarity	NPD6110	Phase 1
0.6118	Remote Similarity	NPD4246	Clinical (unspecified phase)
0.6106	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6105	Remote Similarity	NPD4268	Approved
0.6105	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6105	Remote Similarity	NPD4271	Approved
0.6082	Remote Similarity	NPD4790	Discontinued
0.6061	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6058	Remote Similarity	NPD5778	Approved
0.6058	Remote Similarity	NPD5779	Approved
0.605	Remote Similarity	NPD8294	Approved
0.605	Remote Similarity	NPD8377	Approved
0.6023	Remote Similarity	NPD2685	Clinical (unspecified phase)
0.602	Remote Similarity	NPD4270	Approved
0.602	Remote Similarity	NPD5209	Approved
0.602	Remote Similarity	NPD4269	Approved
0.6019	Remote Similarity	NPD6648	Approved
0.6017	Remote Similarity	NPD7328	Approved
0.6017	Remote Similarity	NPD7327	Approved
0.6016	Remote Similarity	NPD8074	Phase 3
0.6	Remote Similarity	NPD8296	Approved
0.6	Remote Similarity	NPD8378	Approved
0.6	Remote Similarity	NPD8379	Approved
0.6	Remote Similarity	NPD8335	Approved
0.6	Remote Similarity	NPD8033	Approved
0.6	Remote Similarity	NPD1694	Approved
0.6	Remote Similarity	NPD5282	Discontinued
0.6	Remote Similarity	NPD8380	Approved
0.5982	Remote Similarity	NPD6412	Phase 2
0.5979	Remote Similarity	NPD5368	Approved
0.5979	Remote Similarity	NPD4821	Approved
0.5979	Remote Similarity	NPD4822	Approved
0.5979	Remote Similarity	NPD4819	Approved
0.5979	Remote Similarity	NPD4820	Approved
0.5979	Remote Similarity	NPD4252	Approved
0.5976	Remote Similarity	NPD3195	Phase 2
0.5976	Remote Similarity	NPD3730	Approved
0.5976	Remote Similarity	NPD4266	Approved
0.5976	Remote Similarity	NPD3196	Approved
0.5976	Remote Similarity	NPD3728	Approved
0.5976	Remote Similarity	NPD3194	Approved
0.5969	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.5966	Remote Similarity	NPD7516	Approved
0.596	Remote Similarity	NPD5331	Approved
0.596	Remote Similarity	NPD5332	Approved
0.5941	Remote Similarity	NPD5786	Approved
0.5932	Remote Similarity	NPD7115	Discovery
0.5918	Remote Similarity	NPD5369	Approved
0.5902	Remote Similarity	NPD7642	Approved
0.5882	Remote Similarity	NPD6109	Phase 1
0.5882	Remote Similarity	NPD7641	Discontinued
0.5868	Remote Similarity	NPD8444	Approved
0.5862	Remote Similarity	NPD8297	Approved
0.5854	Remote Similarity	NPD3172	Approved
0.5841	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.5826	Remote Similarity	NPD6421	Discontinued
0.5812	Remote Similarity	NPD8133	Approved
0.5812	Remote Similarity	NPD4632	Approved
0.5806	Remote Similarity	NPD8273	Phase 1
0.5802	Remote Similarity	NPD6927	Phase 3
0.5798	Remote Similarity	NPD7500	Approved
0.5795	Remote Similarity	NPD2664	Clinical (unspecified phase)
0.5785	Remote Similarity	NPD6319	Approved
0.5778	Remote Similarity	NPD3704	Approved
0.5776	Remote Similarity	NPD7116	Clinical (unspecified phase)
0.5766	Remote Similarity	NPD7632	Discontinued
0.576	Remote Similarity	NPD7078	Approved
0.5738	Remote Similarity	NPD7503	Approved
0.5726	Remote Similarity	NPD7492	Approved
0.5714	Remote Similarity	NPD7736	Approved
0.5703	Remote Similarity	NPD7260	Phase 2
0.5701	Remote Similarity	NPD7748	Approved
0.5698	Remote Similarity	NPD9119	Approved
0.5698	Remote Similarity	NPD69	Approved
0.5688	Remote Similarity	NPD7902	Approved
0.568	Remote Similarity	NPD8451	Approved
0.568	Remote Similarity	NPD6616	Approved
0.5667	Remote Similarity	NPD7505	Discontinued
0.566	Remote Similarity	NPD7637	Suspended
0.5659	Remote Similarity	NPD6845	Suspended
0.5656	Remote Similarity	NPD6054	Approved
0.5645	Remote Similarity	NPD8328	Phase 3
0.5641	Remote Similarity	NPD2204	Approved
0.5635	Remote Similarity	NPD8448	Approved
0.5635	Remote Similarity	NPD8293	Discontinued
0.5619	Remote Similarity	NPD5370	Suspended
0.5619	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.5619	Remote Similarity	NPD6101	Approved
0.561	Remote Similarity	NPD8267	Approved
0.561	Remote Similarity	NPD29	Approved
0.561	Remote Similarity	NPD28	Approved
0.561	Remote Similarity	NPD8269	Approved
0.561	Remote Similarity	NPD8266	Approved
0.561	Remote Similarity	NPD8268	Approved
0.5607	Remote Similarity	NPD6399	Phase 3
0.5604	Remote Similarity	NPD6108	Clinical (unspecified phase)
0.5604	Remote Similarity	NPD7331	Phase 2
0.5603	Remote Similarity	NPD8132	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