NPASS Compound

Structure

NPC292517 OpenBabel07101718292D 37 42 0 0 1 0 0 0 0 0999 V2000 3.4856 -1.9588 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3315 -0.4937 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7438 2.4365 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1021 -0.0054 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3740 -2.7407 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8856 -1.8948 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9480 2.4365 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7939 1.9481 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7939 -0.9821 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3315 0.4830 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9480 -0.4937 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4856 -0.0054 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8856 -3.5866 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4438 -1.0490 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4205 -2.7407 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6398 1.4598 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4856 -0.9821 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1021 1.9481 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9089 -1.8948 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6398 -0.4937 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.4205 -1.0490 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9554 -0.2031 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7939 0.9714 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 4.3315 1.4598 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4438 0.6428 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7902 1.3687 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.4205 0.6428 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9480 0.4830 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.6398 0.4830 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.1021 0.9714 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.9089 -3.5866 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 5.1774 1.9481 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.1964 3.2795 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.9089 1.4887 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4856 1.9481 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.9089 -0.2031 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 17 2 0 0 0 0 2 17 1 0 0 0 0 3 18 1 0 0 0 0 4 28 1 0 0 0 0 5 6 2 0 0 0 0 5 13 1 0 0 0 0 6 19 1 0 0 0 0 7 8 1 0 0 0 0 7 18 2 0 0 0 0 8 23 1 0 0 0 0 9 11 1 0 0 0 0 9 20 1 0 0 0 0 10 12 1 0 0 0 0 10 24 1 0 0 0 0 11 28 1 0 0 0 0 13 31 2 0 0 0 0 14 21 2 0 0 0 0 14 22 1 0 0 0 0 15 19 2 0 0 0 0 15 31 1 0 0 0 0 16 29 1 0 0 0 0 16 35 1 0 0 0 0 17 20 1 0 0 0 0 19 21 1 0 0 0 0 20 29 1 6 0 0 0 21 36 1 0 0 0 0 22 25 2 0 0 0 0 22 37 1 0 0 0 0 23 28 1 6 0 0 0 23 29 1 0 0 0 0 24 32 2 0 0 0 0 24 35 1 0 0 0 0 25 26 1 0 0 0 0 25 27 1 0 0 0 0 26 30 1 6 0 0 0 26 33 1 0 0 0 0 27 34 2 0 0 0 0 27 36 1 0 0 0 0 28 30 1 1 0 0 0 29 12 1 1 0 0 0 30 18 1 1 0 0 0 30 37 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	503.23
Volume:	516.107
LogP:	3.972
LogD:	3.256
LogS:	-4.471
# Rotatable Bonds:	2
TPSA:	98.86
# H-Bond Aceptor:	7
# H-Bond Donor:	1
# Rings:	6
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.447
Synthetic Accessibility Score:	5.611
Fsp3:	0.5
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:	-4.88
MDCK Permeability:	2.484581091266591e-05
Pgp-inhibitor:	0.097
Pgp-substrate:	0.865
Human Intestinal Absorption (HIA):	0.009
20% Bioavailability (F20%):	0.031
30% Bioavailability (F30%):	0.977

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.858
Plasma Protein Binding (PPB):	82.32950592041016%
Volume Distribution (VD):	1.331
Pgp-substrate:	13.981459617614746%

ADMET: Metabolism

CYP1A2-inhibitor:	0.207
CYP1A2-substrate:	0.34
CYP2C19-inhibitor:	0.455
CYP2C19-substrate:	0.442
CYP2C9-inhibitor:	0.644
CYP2C9-substrate:	0.104
CYP2D6-inhibitor:	0.025
CYP2D6-substrate:	0.136
CYP3A4-inhibitor:	0.938
CYP3A4-substrate:	0.505

ADMET: Excretion

Clearance (CL):	8.634
Half-life (T1/2):	0.422

ADMET: Toxicity

hERG Blockers:	0.621
Human Hepatotoxicity (H-HT):	0.834
Drug-inuced Liver Injury (DILI):	0.929
AMES Toxicity:	0.015
Rat Oral Acute Toxicity:	0.93
Maximum Recommended Daily Dose:	0.99
Skin Sensitization:	0.185
Carcinogencity:	0.212
Eye Corrosion:	0.003
Eye Irritation:	0.013
Respiratory Toxicity:	0.957

Download Data

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

Natural Product: NPC292517

Natural Product ID:	NPC292517
*Common Name:**	Oxalicine A
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	HYMLFCZXNWRIQS-RZUCXZKQSA-N
Standard InCHI:	InChI=1S/C30H33NO6/c1-17(2)20-9-11-28(4)23(29(20)12-10-24(32)35-16-29)8-7-18(3)30(28)26(33)25-22(37-30)14-21(36-27(25)34)19-6-5-13-31-15-19/h5-7,13-15,20,23,26,33H,1,8-12,16H2,2-4H3/t20-,23-,26-,28+,29+,30+/m0/s1
SMILES:	O=C1CC[C@@]2(CO1)[C@@H](CC[C@@]1([C@@H]2CC=C([C@@]21Oc1c([C@@H]2O)c(=O)oc(c1)c1cccnc1)C)C)C(=C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL475274
PubChem CID:	21593945
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001283] Terpene 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
NPO302	Penicillium thiersii	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15787428]
NPO302	Penicillium thiersii	Species	Aspergillaceae	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	1

Activity Type	# Activity
Cell Line	1
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT804	Cell Line	HT-22	Mus musculus	IC50	=	5900.0	nM	PMID[559512]
NPT1192	Organism	Spodoptera frugiperda	Spodoptera frugiperda	Activity	=	98.0	%	PMID[559511]

☑ 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 NPC292517 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	399
0.1-0.2	1687
0.2-0.3	4464
0.3-0.4	11343
0.4-0.5	9593
0.5-0.6	12902
0.6-0.7	1996
0.7-0.8	232
0.8-0.85	70
0.85-0.9	6
0.9-0.95	2
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9843	High Similarity	NPC30570
0.9689	High Similarity	NPC162812
0.9223	High Similarity	NPC475835
0.8895	High Similarity	NPC103230
0.8883	High Similarity	NPC124029
0.8878	High Similarity	NPC477902
0.8792	High Similarity	NPC211920
0.8756	High Similarity	NPC477906
0.8725	High Similarity	NPC216428
0.8713	High Similarity	NPC264674
0.8676	High Similarity	NPC62367
0.867	High Similarity	NPC477910
0.867	High Similarity	NPC42678
0.867	High Similarity	NPC477907
0.867	High Similarity	NPC477909
0.865	High Similarity	NPC48042
0.865	High Similarity	NPC472550
0.865	High Similarity	NPC304179
0.8641	High Similarity	NPC477912
0.8614	High Similarity	NPC472553
0.86	High Similarity	NPC63041
0.8592	High Similarity	NPC477901
0.8565	High Similarity	NPC148860
0.8551	High Similarity	NPC477903
0.8544	High Similarity	NPC472555
0.8537	High Similarity	NPC206343
0.8537	High Similarity	NPC477908
0.8517	High Similarity	NPC26881
0.851	High Similarity	NPC235364
0.851	High Similarity	NPC477911
0.8491	Intermediate Similarity	NPC150698
0.8491	Intermediate Similarity	NPC96801
0.8469	Intermediate Similarity	NPC471980
0.8454	Intermediate Similarity	NPC84815
0.8454	Intermediate Similarity	NPC301368
0.8447	Intermediate Similarity	NPC471016
0.8447	Intermediate Similarity	NPC471014
0.8447	Intermediate Similarity	NPC475408
0.8439	Intermediate Similarity	NPC319128
0.8439	Intermediate Similarity	NPC228331
0.8436	Intermediate Similarity	NPC475601
0.8429	Intermediate Similarity	NPC477899
0.8429	Intermediate Similarity	NPC477900
0.8421	Intermediate Similarity	NPC127026
0.8421	Intermediate Similarity	NPC127720
0.8406	Intermediate Similarity	NPC294579
0.8406	Intermediate Similarity	NPC144779
0.8398	Intermediate Similarity	NPC470306
0.8364	Intermediate Similarity	NPC469748
0.8357	Intermediate Similarity	NPC6981
0.8357	Intermediate Similarity	NPC91125
0.8341	Intermediate Similarity	NPC328154
0.8284	Intermediate Similarity	NPC472752
0.8261	Intermediate Similarity	NPC4421
0.8255	Intermediate Similarity	NPC475498
0.8255	Intermediate Similarity	NPC475137
0.8255	Intermediate Similarity	NPC473850
0.8252	Intermediate Similarity	NPC476467
0.823	Intermediate Similarity	NPC75600
0.823	Intermediate Similarity	NPC6576
0.823	Intermediate Similarity	NPC158020
0.823	Intermediate Similarity	NPC473089
0.823	Intermediate Similarity	NPC473115
0.823	Intermediate Similarity	NPC212768
0.8224	Intermediate Similarity	NPC471190
0.8224	Intermediate Similarity	NPC471977
0.8224	Intermediate Similarity	NPC470486
0.8224	Intermediate Similarity	NPC475644
0.8208	Intermediate Similarity	NPC250807
0.8208	Intermediate Similarity	NPC57797
0.8208	Intermediate Similarity	NPC76565
0.8203	Intermediate Similarity	NPC475426
0.8203	Intermediate Similarity	NPC35208
0.8194	Intermediate Similarity	NPC30456
0.8178	Intermediate Similarity	NPC475631
0.8178	Intermediate Similarity	NPC477787
0.8178	Intermediate Similarity	NPC476110
0.8178	Intermediate Similarity	NPC328186
0.8178	Intermediate Similarity	NPC122968
0.8178	Intermediate Similarity	NPC87152
0.8178	Intermediate Similarity	NPC228377
0.8178	Intermediate Similarity	NPC475600
0.8157	Intermediate Similarity	NPC238278
0.8148	Intermediate Similarity	NPC475303
0.8148	Intermediate Similarity	NPC475596
0.8148	Intermediate Similarity	NPC316841
0.814	Intermediate Similarity	NPC475362
0.8136	Intermediate Similarity	NPC253482
0.8131	Intermediate Similarity	NPC473506
0.8119	Intermediate Similarity	NPC327769
0.8119	Intermediate Similarity	NPC170751
0.8108	Intermediate Similarity	NPC475648
0.8093	Intermediate Similarity	NPC146824
0.8088	Intermediate Similarity	NPC289086
0.8084	Intermediate Similarity	NPC233727
0.8073	Intermediate Similarity	NPC237702
0.8065	Intermediate Similarity	NPC292416
0.8065	Intermediate Similarity	NPC473689
0.8048	Intermediate Similarity	NPC62844
0.8048	Intermediate Similarity	NPC193361
0.8037	Intermediate Similarity	NPC475406
0.8028	Intermediate Similarity	NPC244839
0.8028	Intermediate Similarity	NPC319880
0.8028	Intermediate Similarity	NPC320324
0.8009	Intermediate Similarity	NPC14116
0.8009	Intermediate Similarity	NPC285411
0.8	Intermediate Similarity	NPC327904
0.8	Intermediate Similarity	NPC38959
0.7991	Intermediate Similarity	NPC477788
0.799	Intermediate Similarity	NPC323551
0.799	Intermediate Similarity	NPC280473
0.7972	Intermediate Similarity	NPC311196
0.7972	Intermediate Similarity	NPC134384
0.7972	Intermediate Similarity	NPC187494
0.7952	Intermediate Similarity	NPC51008
0.7952	Intermediate Similarity	NPC41724
0.7945	Intermediate Similarity	NPC213143
0.7857	Intermediate Similarity	NPC470189
0.7857	Intermediate Similarity	NPC40919
0.7843	Intermediate Similarity	NPC50997
0.7843	Intermediate Similarity	NPC160127
0.7832	Intermediate Similarity	NPC148896
0.7832	Intermediate Similarity	NPC471013
0.7832	Intermediate Similarity	NPC180668
0.7826	Intermediate Similarity	NPC471015
0.782	Intermediate Similarity	NPC111732
0.7805	Intermediate Similarity	NPC470279
0.7804	Intermediate Similarity	NPC319556
0.7799	Intermediate Similarity	NPC470190
0.7794	Intermediate Similarity	NPC320748
0.7794	Intermediate Similarity	NPC324245
0.7789	Intermediate Similarity	NPC325775
0.7789	Intermediate Similarity	NPC328798
0.7783	Intermediate Similarity	NPC165837
0.7767	Intermediate Similarity	NPC32451
0.7767	Intermediate Similarity	NPC328559
0.7745	Intermediate Similarity	NPC329024
0.7719	Intermediate Similarity	NPC475533
0.7718	Intermediate Similarity	NPC79223
0.771	Intermediate Similarity	NPC207531
0.7703	Intermediate Similarity	NPC309498
0.7696	Intermediate Similarity	NPC10904
0.7696	Intermediate Similarity	NPC253314
0.7686	Intermediate Similarity	NPC324619
0.7686	Intermediate Similarity	NPC475315
0.7677	Intermediate Similarity	NPC327373
0.7675	Intermediate Similarity	NPC476090
0.7667	Intermediate Similarity	NPC156044
0.766	Intermediate Similarity	NPC473833
0.7623	Intermediate Similarity	NPC471004
0.7621	Intermediate Similarity	NPC317672
0.7621	Intermediate Similarity	NPC59033
0.7619	Intermediate Similarity	NPC476516
0.7598	Intermediate Similarity	NPC289786
0.7595	Intermediate Similarity	NPC471978
0.7588	Intermediate Similarity	NPC322043
0.7588	Intermediate Similarity	NPC325093
0.7586	Intermediate Similarity	NPC127647
0.7576	Intermediate Similarity	NPC471997
0.7571	Intermediate Similarity	NPC12944
0.7571	Intermediate Similarity	NPC25442
0.7564	Intermediate Similarity	NPC475301
0.7564	Intermediate Similarity	NPC53255
0.7564	Intermediate Similarity	NPC326930
0.7564	Intermediate Similarity	NPC85879
0.7532	Intermediate Similarity	NPC13603
0.7521	Intermediate Similarity	NPC328928
0.7512	Intermediate Similarity	NPC318020
0.7488	Intermediate Similarity	NPC182814
0.7427	Intermediate Similarity	NPC471979
0.7397	Intermediate Similarity	NPC314270
0.7376	Intermediate Similarity	NPC2395
0.7371	Intermediate Similarity	NPC476517
0.7346	Intermediate Similarity	NPC155792
0.7317	Intermediate Similarity	NPC44354
0.7308	Intermediate Similarity	NPC20593
0.7294	Intermediate Similarity	NPC317752
0.7277	Intermediate Similarity	NPC235885
0.7273	Intermediate Similarity	NPC473053
0.7251	Intermediate Similarity	NPC123395
0.7248	Intermediate Similarity	NPC318299
0.7248	Intermediate Similarity	NPC151976
0.7245	Intermediate Similarity	NPC477975
0.7212	Intermediate Similarity	NPC57690
0.7206	Intermediate Similarity	NPC207851
0.7204	Intermediate Similarity	NPC102008
0.72	Intermediate Similarity	NPC141428
0.7194	Intermediate Similarity	NPC474217
0.719	Intermediate Similarity	NPC109922
0.7162	Intermediate Similarity	NPC82070
0.7149	Intermediate Similarity	NPC204491
0.7143	Intermediate Similarity	NPC127677
0.7143	Intermediate Similarity	NPC317010
0.7143	Intermediate Similarity	NPC146724
0.7143	Intermediate Similarity	NPC71079
0.713	Intermediate Similarity	NPC238457
0.7125	Intermediate Similarity	NPC478045
0.7119	Intermediate Similarity	NPC107123
0.7097	Intermediate Similarity	NPC474905
0.7097	Intermediate Similarity	NPC46225

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 NPC292517 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	260
0.1-0.2	587
0.2-0.3	859
0.3-0.4	1950
0.4-0.5	2782
0.5-0.6	2136
0.6-0.7	552
0.7-0.8	24
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
0.7642	Intermediate Similarity	NPD8468	Phase 2
0.7614	Intermediate Similarity	NPD8304	Clinical (unspecified phase)
0.7593	Intermediate Similarity	NPD8327	Clinical (unspecified phase)
0.7593	Intermediate Similarity	NPD8326	Phase 3
0.7593	Intermediate Similarity	NPD8325	Phase 3
0.7461	Intermediate Similarity	NPD5088	Discontinued
0.7461	Intermediate Similarity	NPD6635	Approved
0.743	Intermediate Similarity	NPD6529	Discontinued
0.7387	Intermediate Similarity	NPD6641	Approved
0.7387	Intermediate Similarity	NPD5751	Clinical (unspecified phase)
0.7387	Intermediate Similarity	NPD6642	Approved
0.7327	Intermediate Similarity	NPD7069	Discontinued
0.7324	Intermediate Similarity	NPD7396	Approved
0.7233	Intermediate Similarity	NPD7234	Approved
0.7233	Intermediate Similarity	NPD7233	Approved
0.723	Intermediate Similarity	NPD5721	Clinical (unspecified phase)
0.7225	Intermediate Similarity	NPD5975	Clinical (unspecified phase)
0.7204	Intermediate Similarity	NPD53	Approved
0.7204	Intermediate Similarity	NPD7778	Approved
0.7204	Intermediate Similarity	NPD7777	Approved
0.7202	Intermediate Similarity	NPD6026	Approved
0.7202	Intermediate Similarity	NPD7927	Clinical (unspecified phase)
0.7177	Intermediate Similarity	NPD6361	Phase 2
0.715	Intermediate Similarity	NPD6477	Clinical (unspecified phase)
0.7136	Intermediate Similarity	NPD3794	Approved
0.7136	Intermediate Similarity	NPD3795	Approved
0.713	Intermediate Similarity	NPD4901	Clinical (unspecified phase)
0.7115	Intermediate Similarity	NPD8063	Discontinued
0.7112	Intermediate Similarity	NPD8409	Suspended
0.7092	Intermediate Similarity	NPD2511	Approved
0.7064	Intermediate Similarity	NPD1483	Discontinued
0.7061	Intermediate Similarity	NPD4086	Phase 1
0.7051	Intermediate Similarity	NPD7010	Phase 3
0.704	Intermediate Similarity	NPD4989	Phase 2
0.7029	Intermediate Similarity	NPD6525	Clinical (unspecified phase)
0.7022	Intermediate Similarity	NPD8479	Phase 2
0.7	Intermediate Similarity	NPD4900	Clinical (unspecified phase)
0.699	Remote Similarity	NPD820	Phase 3
0.6981	Remote Similarity	NPD4427	Phase 2
0.6979	Remote Similarity	NPD7886	Phase 2
0.6979	Remote Similarity	NPD7885	Phase 2
0.6977	Remote Similarity	NPD4396	Clinical (unspecified phase)
0.6948	Remote Similarity	NPD7061	Clinical (unspecified phase)
0.6941	Remote Similarity	NPD7562	Approved
0.6931	Remote Similarity	NPD6739	Clinical (unspecified phase)
0.693	Remote Similarity	NPD6661	Clinical (unspecified phase)
0.6916	Remote Similarity	NPD6298	Discontinued
0.6897	Remote Similarity	NPD8372	Clinical (unspecified phase)
0.689	Remote Similarity	NPD4375	Approved
0.6872	Remote Similarity	NPD3321	Discontinued
0.687	Remote Similarity	NPD7426	Phase 1
0.686	Remote Similarity	NPD7414	Clinical (unspecified phase)
0.6854	Remote Similarity	NPD4526	Approved
0.6854	Remote Similarity	NPD4528	Approved
0.6854	Remote Similarity	NPD4529	Approved
0.6853	Remote Similarity	NPD8052	Clinical (unspecified phase)
0.6847	Remote Similarity	NPD485	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD4889	Approved
0.6842	Remote Similarity	NPD5147	Discontinued
0.6837	Remote Similarity	NPD6206	Phase 1
0.6825	Remote Similarity	NPD2896	Discontinued
0.6818	Remote Similarity	NPD6732	Clinical (unspecified phase)
0.6808	Remote Similarity	NPD6665	Discontinued
0.6803	Remote Similarity	NPD8370	Discontinued
0.68	Remote Similarity	NPD4897	Phase 2
0.68	Remote Similarity	NPD7707	Approved
0.6798	Remote Similarity	NPD3280	Approved
0.6777	Remote Similarity	NPD8020	Approved
0.6777	Remote Similarity	NPD6257	Clinical (unspecified phase)
0.6777	Remote Similarity	NPD8021	Approved
0.6773	Remote Similarity	NPD4035	Approved
0.6773	Remote Similarity	NPD4039	Approved
0.6773	Remote Similarity	NPD4037	Approved
0.6773	Remote Similarity	NPD4034	Approved
0.6773	Remote Similarity	NPD4033	Approved
0.6773	Remote Similarity	NPD31	Approved
0.6773	Remote Similarity	NPD4122	Approved
0.6773	Remote Similarity	NPD4038	Approved
0.6773	Remote Similarity	NPD32	Approved
0.6773	Remote Similarity	NPD4036	Approved
0.6771	Remote Similarity	NPD6262	Clinical (unspecified phase)
0.677	Remote Similarity	NPD3394	Approved
0.677	Remote Similarity	NPD3389	Approved
0.677	Remote Similarity	NPD3393	Approved
0.6769	Remote Similarity	NPD5506	Approved
0.6769	Remote Similarity	NPD5507	Approved
0.6763	Remote Similarity	NPD1620	Clinical (unspecified phase)
0.6761	Remote Similarity	NPD7955	Approved
0.6761	Remote Similarity	NPD2336	Approved
0.6761	Remote Similarity	NPD7956	Approved
0.6761	Remote Similarity	NPD3785	Clinical (unspecified phase)
0.6759	Remote Similarity	NPD5003	Discontinued
0.6749	Remote Similarity	NPD6872	Clinical (unspecified phase)
0.6748	Remote Similarity	NPD8373	Clinical (unspecified phase)
0.6745	Remote Similarity	NPD4021	Phase 2
0.6745	Remote Similarity	NPD4334	Discontinued
0.6743	Remote Similarity	NPD4501	Approved
0.6743	Remote Similarity	NPD4500	Approved
0.6741	Remote Similarity	NPD4417	Approved
0.6736	Remote Similarity	NPD6276	Discontinued
0.6734	Remote Similarity	NPD2581	Approved
0.6734	Remote Similarity	NPD2582	Approved
0.6734	Remote Similarity	NPD7708	Approved
0.6724	Remote Similarity	NPD5640	Discontinued
0.6723	Remote Similarity	NPD7797	Approved
0.6723	Remote Similarity	NPD7796	Approved
0.6714	Remote Similarity	NPD2544	Clinical (unspecified phase)
0.6711	Remote Similarity	NPD7878	Phase 2
0.6709	Remote Similarity	NPD5891	Approved
0.6699	Remote Similarity	NPD3386	Phase 2
0.6698	Remote Similarity	NPD4551	Phase 2
0.6693	Remote Similarity	NPD7803	Approved
0.6682	Remote Similarity	NPD2509	Approved
0.6682	Remote Similarity	NPD2510	Approved
0.6682	Remote Similarity	NPD8485	Approved
0.6667	Remote Similarity	NPD7470	Discontinued
0.6667	Remote Similarity	NPD5100	Phase 3
0.6667	Remote Similarity	NPD4862	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6479	Discontinued
0.6667	Remote Similarity	NPD4600	Approved
0.6667	Remote Similarity	NPD4601	Approved
0.6652	Remote Similarity	NPD5148	Clinical (unspecified phase)
0.6652	Remote Similarity	NPD5513	Phase 2
0.6652	Remote Similarity	NPD5487	Phase 1
0.6652	Remote Similarity	NPD5149	Phase 2
0.6652	Remote Similarity	NPD8289	Discontinued
0.6651	Remote Similarity	NPD5898	Approved
0.6651	Remote Similarity	NPD6569	Phase 2
0.6651	Remote Similarity	NPD6261	Phase 3
0.6651	Remote Similarity	NPD5899	Approved
0.6651	Remote Similarity	NPD5897	Approved
0.6651	Remote Similarity	NPD4376	Phase 3
0.665	Remote Similarity	NPD6183	Clinical (unspecified phase)
0.665	Remote Similarity	NPD43	Approved
0.665	Remote Similarity	NPD6182	Approved
0.6649	Remote Similarity	NPD751	Clinical (unspecified phase)
0.6649	Remote Similarity	NPD203	Clinical (unspecified phase)
0.6649	Remote Similarity	NPD3813	Approved
0.6639	Remote Similarity	NPD8412	Phase 1
0.6638	Remote Similarity	NPD7589	Clinical (unspecified phase)
0.6637	Remote Similarity	NPD6657	Clinical (unspecified phase)
0.6636	Remote Similarity	NPD2307	Discontinued
0.6636	Remote Similarity	NPD2564	Approved
0.6636	Remote Similarity	NPD2565	Phase 2
0.6636	Remote Similarity	NPD4081	Clinical (unspecified phase)
0.6636	Remote Similarity	NPD6281	Approved
0.6635	Remote Similarity	NPD1032	Phase 2
0.6633	Remote Similarity	NPD2809	Approved
0.6633	Remote Similarity	NPD9271	Approved
0.6622	Remote Similarity	NPD2831	Approved
0.6622	Remote Similarity	NPD3946	Clinical (unspecified phase)
0.6621	Remote Similarity	NPD6249	Phase 2
0.6621	Remote Similarity	NPD6248	Phase 2
0.662	Remote Similarity	NPD6791	Phase 2
0.6617	Remote Similarity	NPD5255	Approved
0.6609	Remote Similarity	NPD3925	Approved
0.6607	Remote Similarity	NPD7947	Clinical (unspecified phase)
0.6602	Remote Similarity	NPD1078	Clinical (unspecified phase)
0.6597	Remote Similarity	NPD7807	Clinical (unspecified phase)
0.6595	Remote Similarity	NPD8356	Approved
0.6594	Remote Similarity	NPD3326	Clinical (unspecified phase)
0.6592	Remote Similarity	NPD7958	Clinical (unspecified phase)
0.6592	Remote Similarity	NPD7957	Phase 1
0.6591	Remote Similarity	NPD8486	Clinical (unspecified phase)
0.6584	Remote Similarity	NPD7967	Discontinued
0.6578	Remote Similarity	NPD4437	Phase 3
0.6578	Remote Similarity	NPD4506	Discontinued
0.6577	Remote Similarity	NPD2121	Clinical (unspecified phase)
0.6574	Remote Similarity	NPD3924	Approved
0.6574	Remote Similarity	NPD3921	Approved
0.6574	Remote Similarity	NPD3922	Approved
0.6574	Remote Similarity	NPD3923	Approved
0.6574	Remote Similarity	NPD4315	Phase 2
0.6565	Remote Similarity	NPD1926	Approved
0.6565	Remote Similarity	NPD7395	Discontinued
0.6555	Remote Similarity	NPD7558	Phase 2
0.6553	Remote Similarity	NPD6553	Clinical (unspecified phase)
0.6547	Remote Similarity	NPD6323	Clinical (unspecified phase)
0.6547	Remote Similarity	NPD5901	Discontinued
0.6547	Remote Similarity	NPD3947	Discontinued
0.6546	Remote Similarity	NPD4805	Approved
0.6545	Remote Similarity	NPD6874	Approved
0.6545	Remote Similarity	NPD3800	Clinical (unspecified phase)
0.6545	Remote Similarity	NPD5482	Discontinued
0.6545	Remote Similarity	NPD8101	Phase 3
0.6538	Remote Similarity	NPD5322	Clinical (unspecified phase)
0.6537	Remote Similarity	NPD4174	Clinical (unspecified phase)
0.6532	Remote Similarity	NPD7561	Approved
0.6531	Remote Similarity	NPD9074	Approved
0.6531	Remote Similarity	NPD9075	Approved
0.653	Remote Similarity	NPD7021	Clinical (unspecified phase)
0.6529	Remote Similarity	NPD7417	Discontinued
0.6526	Remote Similarity	NPD6241	Phase 1
0.6518	Remote Similarity	NPD7001	Phase 3
0.6516	Remote Similarity	NPD5497	Clinical (unspecified phase)
0.6514	Remote Similarity	NPD3395	Approved
0.6514	Remote Similarity	NPD3396	Approved
0.6507	Remote Similarity	NPD8112	Clinical (unspecified phase)
0.6498	Remote Similarity	NPD4950	Approved
0.6495	Remote Similarity	NPD5444	Phase 1

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