NPASS Compound

Structure

CID320064 OpenBabel06191716152D 34 37 0 0 1 0 0 0 0 0999 V2000 -4.3301 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -1.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -1.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8660 3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 -1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.1962 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.7321 -1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.3301 0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.7321 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.4641 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8660 0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.7321 3.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 4.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2 23 1 0 0 0 0 3 4 2 0 0 0 0 3 5 1 0 0 0 0 4 6 1 0 0 0 0 5 10 2 0 0 0 0 6 11 2 0 0 0 0 7 12 2 0 0 0 0 7 14 1 0 0 0 0 8 24 1 0 0 0 0 9 1 1 1 0 0 0 9 15 1 0 0 0 0 9 31 1 0 0 0 0 10 11 1 0 0 0 0 10 12 1 0 0 0 0 11 23 1 0 0 0 0 12 32 1 0 0 0 0 13 8 1 6 0 0 0 13 16 1 0 0 0 0 13 33 1 0 0 0 0 14 23 1 0 0 0 0 14 25 2 0 0 0 0 15 17 1 0 0 0 0 15 26 1 6 0 0 0 16 18 1 0 0 0 0 16 27 1 1 0 0 0 17 19 1 0 0 0 0 17 28 1 1 0 0 0 18 20 1 0 0 0 0 18 29 1 6 0 0 0 19 21 1 0 0 0 0 19 30 1 1 0 0 0 20 22 1 0 0 0 0 20 34 1 1 0 0 0 21 31 1 0 0 0 0 21 34 1 6 0 0 0 22 32 1 6 0 0 0 22 33 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	483.17
Volume:	449.349
LogP:	-0.372
LogD:	-0.35
LogS:	-2.089
# Rotatable Bonds:	5
TPSA:	180.3
# H-Bond Aceptor:	12
# H-Bond Donor:	6
# Rings:	4
# Heavy Atoms:	12

MedChem Properties

QED Drug-Likeness Score:	0.266
Synthetic Accessibility Score:	4.363
Fsp3:	0.591
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
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:	-6.412
MDCK Permeability:	6.317777297226712e-05
Pgp-inhibitor:	0.022
Pgp-substrate:	0.99
Human Intestinal Absorption (HIA):	0.954
20% Bioavailability (F20%):	0.015
30% Bioavailability (F30%):	0.997

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.238
Plasma Protein Binding (PPB):	63.0186767578125%
Volume Distribution (VD):	0.477
Pgp-substrate:	28.66377830505371%

ADMET: Metabolism

CYP1A2-inhibitor:	0.041
CYP1A2-substrate:	0.113
CYP2C19-inhibitor:	0.015
CYP2C19-substrate:	0.757
CYP2C9-inhibitor:	0.001
CYP2C9-substrate:	0.1
CYP2D6-inhibitor:	0.006
CYP2D6-substrate:	0.133
CYP3A4-inhibitor:	0.005
CYP3A4-substrate:	0.023

ADMET: Excretion

Clearance (CL):	1.084
Half-life (T1/2):	0.703

ADMET: Toxicity

hERG Blockers:	0.09
Human Hepatotoxicity (H-HT):	0.143
Drug-inuced Liver Injury (DILI):	0.473
AMES Toxicity:	0.268
Rat Oral Acute Toxicity:	0.034
Maximum Recommended Daily Dose:	0.003
Skin Sensitization:	0.338
Carcinogencity:	0.187
Eye Corrosion:	0.003
Eye Irritation:	0.133
Respiratory Toxicity:	0.037

Download Data

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

Natural Product: NPC320064

Natural Product ID:	NPC320064
*Common Name:**	Katimborine
IUPAC Name:	4-[(2S,3R,4S,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyoxan-2-yl]oxy-1-methylquinolin-2-one
Synonyms:	katimborine
Standard InCHIKey:	ASAXLUXKTGJUKN-KNEOXYRNSA-N
Standard InCHI:	InChI=1S/C22H29NO11/c1-9-15(26)17(28)19(30)21(31-9)34-20-18(29)16(27)13(8-24)33-22(20)32-12-7-14(25)23(2)11-6-4-3-5-10(11)12/h3-7,9,13,15-22,24,26-30H,8H2,1-2H3/t9-,13+,15-,16+,17+,18-,19+,20+,21-,22+/m0/s1
SMILES:	CC1C(C(C(C(O1)OC2C(C(C(OC2OC3=CC(=O)N(C4=CC=CC=C43)C)CO)O)O)O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1928407
PubChem CID:	56602472
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0001253] Quinolines and derivatives [CHEMONTID:0000056] Quinolones and derivatives [CHEMONTID:0001716] Hydroquinolones

*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
NPO1762	Citropsis articulata	Species	Rutaceae	Eukaryota	Root Bark	n.a.	n.a.	PMID[21985060]
NPO1762	Citropsis articulata	Species	Rutaceae	Eukaryota	n.a.	root	n.a.	PMID[21985060]
NPO1762	Citropsis articulata	Species	Rutaceae	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
EC50	2
IC50	2

Activity Type	# Activity
Cell Line	1
Organism	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT189	Cell Line	Vero	Chlorocebus aethiops	IC50	>	50.0	ug.mL-1	PMID[543536]
NPT1225	Organism	Plasmodium falciparum (isolate FcB1 / Columbia)	Plasmodium falciparum FcB1/Columbia	IC50	>	100.0	ug.mL-1	PMID[543536]
NPT633	Organism	Leishmania donovani	Leishmania donovani	EC50	>	125.0	ug.mL-1	PMID[543536]
NPT471	Organism	Trypanosoma brucei brucei	Trypanosoma brucei brucei	EC50	>	125.0	ug.mL-1	PMID[543536]

☑ 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 NPC320064 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	368
0.1-0.2	1853
0.2-0.3	7921
0.3-0.4	9693
0.4-0.5	9893
0.5-0.6	10826
0.6-0.7	1906
0.7-0.8	225
0.8-0.85	11
0.85-0.9	0
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.8027	Intermediate Similarity	NPC250476
0.7933	Intermediate Similarity	NPC231382
0.7931	Intermediate Similarity	NPC291759
0.7874	Intermediate Similarity	NPC133591
0.7829	Intermediate Similarity	NPC38823
0.7829	Intermediate Similarity	NPC207033
0.761	Intermediate Similarity	NPC308197
0.7588	Intermediate Similarity	NPC470971
0.7446	Intermediate Similarity	NPC472191
0.7378	Intermediate Similarity	NPC242000
0.734	Intermediate Similarity	NPC311357
0.7333	Intermediate Similarity	NPC262725
0.7292	Intermediate Similarity	NPC477548
0.7273	Intermediate Similarity	NPC129624
0.72	Intermediate Similarity	NPC14950
0.7159	Intermediate Similarity	NPC307640
0.7143	Intermediate Similarity	NPC248903
0.7135	Intermediate Similarity	NPC220560
0.7114	Intermediate Similarity	NPC148124
0.7095	Intermediate Similarity	NPC287152
0.7094	Intermediate Similarity	NPC26928
0.7079	Intermediate Similarity	NPC290069
0.7065	Intermediate Similarity	NPC99724
0.7065	Intermediate Similarity	NPC316405
0.7052	Intermediate Similarity	NPC253667
0.7052	Intermediate Similarity	NPC35510
0.7005	Intermediate Similarity	NPC471825
0.6943	Remote Similarity	NPC475448
0.6943	Remote Similarity	NPC246983
0.6939	Remote Similarity	NPC30563
0.6936	Remote Similarity	NPC301163
0.6914	Remote Similarity	NPC139506
0.6914	Remote Similarity	NPC292143
0.6891	Remote Similarity	NPC475223
0.6871	Remote Similarity	NPC474148
0.6871	Remote Similarity	NPC276061
0.6842	Remote Similarity	NPC216605
0.6842	Remote Similarity	NPC266389
0.6842	Remote Similarity	NPC122245
0.6834	Remote Similarity	NPC244856
0.6831	Remote Similarity	NPC116096
0.6815	Remote Similarity	NPC325013
0.68	Remote Similarity	NPC306644
0.68	Remote Similarity	NPC236424
0.6771	Remote Similarity	NPC324245
0.6771	Remote Similarity	NPC320748
0.6766	Remote Similarity	NPC274842
0.6763	Remote Similarity	NPC471073
0.6763	Remote Similarity	NPC270811
0.6751	Remote Similarity	NPC474905
0.6738	Remote Similarity	NPC328798
0.6738	Remote Similarity	NPC325775
0.6736	Remote Similarity	NPC267414
0.6721	Remote Similarity	NPC49353
0.672	Remote Similarity	NPC127647
0.6708	Remote Similarity	NPC314473
0.6705	Remote Similarity	NPC471132
0.6703	Remote Similarity	NPC327373
0.6701	Remote Similarity	NPC79223
0.6701	Remote Similarity	NPC309498
0.6698	Remote Similarity	NPC99891
0.6686	Remote Similarity	NPC136951
0.6686	Remote Similarity	NPC161155
0.6686	Remote Similarity	NPC97004
0.6685	Remote Similarity	NPC472106
0.6685	Remote Similarity	NPC85613
0.6682	Remote Similarity	NPC472434
0.6667	Remote Similarity	NPC229600
0.6667	Remote Similarity	NPC32451
0.6667	Remote Similarity	NPC328559
0.6667	Remote Similarity	NPC470825
0.6647	Remote Similarity	NPC97282
0.6632	Remote Similarity	NPC329024
0.663	Remote Similarity	NPC475094
0.6629	Remote Similarity	NPC10875
0.6629	Remote Similarity	NPC112766
0.6629	Remote Similarity	NPC313757
0.6629	Remote Similarity	NPC10730
0.6626	Remote Similarity	NPC138777
0.6626	Remote Similarity	NPC246869
0.6626	Remote Similarity	NPC225384
0.6625	Remote Similarity	NPC114096
0.6614	Remote Similarity	NPC182814
0.6613	Remote Similarity	NPC325093
0.6613	Remote Similarity	NPC322043
0.6605	Remote Similarity	NPC295970
0.66	Remote Similarity	NPC264784
0.6599	Remote Similarity	NPC476115
0.6599	Remote Similarity	NPC37714
0.6599	Remote Similarity	NPC152384
0.6587	Remote Similarity	NPC36434
0.6585	Remote Similarity	NPC184437
0.6585	Remote Similarity	NPC174788
0.6584	Remote Similarity	NPC148026
0.6583	Remote Similarity	NPC156044
0.6579	Remote Similarity	NPC120217
0.6575	Remote Similarity	NPC469915
0.6573	Remote Similarity	NPC472120
0.6573	Remote Similarity	NPC472101
0.6573	Remote Similarity	NPC472117
0.6566	Remote Similarity	NPC268077
0.6564	Remote Similarity	NPC160127
0.6564	Remote Similarity	NPC50997
0.6548	Remote Similarity	NPC298821
0.6543	Remote Similarity	NPC318020
0.6529	Remote Similarity	NPC178466
0.6529	Remote Similarity	NPC63628
0.6524	Remote Similarity	NPC235294
0.6524	Remote Similarity	NPC46137
0.6518	Remote Similarity	NPC472435
0.6517	Remote Similarity	NPC477160
0.6515	Remote Similarity	NPC207971
0.6513	Remote Similarity	NPC317672
0.6513	Remote Similarity	NPC59033
0.6509	Remote Similarity	NPC123761
0.6505	Remote Similarity	NPC5167
0.6505	Remote Similarity	NPC82070
0.6502	Remote Similarity	NPC111732
0.65	Remote Similarity	NPC57607
0.65	Remote Similarity	NPC70172
0.65	Remote Similarity	NPC145287
0.6497	Remote Similarity	NPC70549
0.6489	Remote Similarity	NPC97584
0.6488	Remote Similarity	NPC315051
0.6486	Remote Similarity	NPC127082
0.6482	Remote Similarity	NPC25442
0.6482	Remote Similarity	NPC12944
0.6481	Remote Similarity	NPC106677
0.648	Remote Similarity	NPC85651
0.6478	Remote Similarity	NPC476142
0.6467	Remote Similarity	NPC184633
0.6463	Remote Similarity	NPC319995
0.6463	Remote Similarity	NPC289415
0.6463	Remote Similarity	NPC469527
0.6458	Remote Similarity	NPC129909
0.6447	Remote Similarity	NPC127178
0.6446	Remote Similarity	NPC173295
0.6443	Remote Similarity	NPC21483
0.6443	Remote Similarity	NPC198205
0.6441	Remote Similarity	NPC140915
0.6441	Remote Similarity	NPC10221
0.6441	Remote Similarity	NPC305700
0.6441	Remote Similarity	NPC187028
0.6441	Remote Similarity	NPC197741
0.6441	Remote Similarity	NPC18249
0.644	Remote Similarity	NPC477998
0.6436	Remote Similarity	NPC477159
0.6433	Remote Similarity	NPC282578
0.6432	Remote Similarity	NPC472436
0.6429	Remote Similarity	NPC71124
0.6429	Remote Similarity	NPC311054
0.6429	Remote Similarity	NPC112752
0.6425	Remote Similarity	NPC19023
0.6425	Remote Similarity	NPC93653
0.6425	Remote Similarity	NPC474058
0.642	Remote Similarity	NPC276047
0.642	Remote Similarity	NPC267733
0.642	Remote Similarity	NPC471157
0.6414	Remote Similarity	NPC136573
0.6414	Remote Similarity	NPC176371
0.6413	Remote Similarity	NPC276993
0.6413	Remote Similarity	NPC293255
0.6413	Remote Similarity	NPC181138
0.6413	Remote Similarity	NPC298851
0.6413	Remote Similarity	NPC210415
0.6413	Remote Similarity	NPC21752
0.641	Remote Similarity	NPC162653
0.6409	Remote Similarity	NPC24954
0.6406	Remote Similarity	NPC105055
0.6406	Remote Similarity	NPC314702
0.6406	Remote Similarity	NPC22689
0.6404	Remote Similarity	NPC25961
0.6402	Remote Similarity	NPC253595
0.64	Remote Similarity	NPC87714
0.64	Remote Similarity	NPC139699
0.64	Remote Similarity	NPC114659
0.6398	Remote Similarity	NPC186669
0.6396	Remote Similarity	NPC90358
0.6396	Remote Similarity	NPC5374
0.6396	Remote Similarity	NPC107828
0.6394	Remote Similarity	NPC52254
0.6392	Remote Similarity	NPC254957
0.6391	Remote Similarity	NPC101686
0.6391	Remote Similarity	NPC469364
0.6391	Remote Similarity	NPC65262
0.639	Remote Similarity	NPC217903
0.639	Remote Similarity	NPC151781
0.639	Remote Similarity	NPC74562
0.639	Remote Similarity	NPC316181
0.638	Remote Similarity	NPC81092
0.638	Remote Similarity	NPC197680
0.638	Remote Similarity	NPC288416
0.638	Remote Similarity	NPC103605
0.638	Remote Similarity	NPC259098
0.638	Remote Similarity	NPC101372
0.6378	Remote Similarity	NPC198390
0.6377	Remote Similarity	NPC162812
0.6375	Remote Similarity	NPC52097
0.6374	Remote Similarity	NPC19555
0.6374	Remote Similarity	NPC168750

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 NPC320064 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	237
0.1-0.2	585
0.2-0.3	962
0.3-0.4	1484
0.4-0.5	2689
0.5-0.6	2405
0.6-0.7	696
0.7-0.8	92
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
0.7613	Intermediate Similarity	NPD2791	Discontinued
0.7284	Intermediate Similarity	NPD4430	Phase 2
0.7151	Intermediate Similarity	NPD4871	Phase 2
0.7151	Intermediate Similarity	NPD2995	Approved
0.7135	Intermediate Similarity	NPD5521	Clinical (unspecified phase)
0.7095	Intermediate Similarity	NPD5900	Clinical (unspecified phase)
0.7039	Intermediate Similarity	NPD3793	Phase 3
0.6982	Remote Similarity	NPD3277	Phase 3
0.6931	Remote Similarity	NPD5582	Discontinued
0.6914	Remote Similarity	NPD3789	Approved
0.6864	Remote Similarity	NPD8389	Clinical (unspecified phase)
0.6845	Remote Similarity	NPD3278	Clinical (unspecified phase)
0.6837	Remote Similarity	NPD7263	Phase 2
0.6826	Remote Similarity	NPD2387	Approved
0.6734	Remote Similarity	NPD4900	Clinical (unspecified phase)
0.6724	Remote Similarity	NPD2836	Approved
0.6722	Remote Similarity	NPD2388	Discontinued
0.6707	Remote Similarity	NPD4168	Approved
0.6702	Remote Similarity	NPD6608	Clinical (unspecified phase)
0.6701	Remote Similarity	NPD4901	Clinical (unspecified phase)
0.6685	Remote Similarity	NPD6496	Clinical (unspecified phase)
0.6685	Remote Similarity	NPD6211	Clinical (unspecified phase)
0.6684	Remote Similarity	NPD7064	Clinical (unspecified phase)
0.663	Remote Similarity	NPD2215	Approved
0.663	Remote Similarity	NPD2216	Approved
0.6593	Remote Similarity	NPD5997	Discontinued
0.6587	Remote Similarity	NPD3605	Approved
0.6587	Remote Similarity	NPD3068	Approved
0.6582	Remote Similarity	NPD519	Approved
0.658	Remote Similarity	NPD7880	Clinical (unspecified phase)
0.6575	Remote Similarity	NPD5847	Phase 1
0.657	Remote Similarity	NPD7528	Approved
0.6566	Remote Similarity	NPD5102	Clinical (unspecified phase)
0.6566	Remote Similarity	NPD2670	Approved
0.6557	Remote Similarity	NPD5938	Phase 3
0.6552	Remote Similarity	NPD1678	Clinical (unspecified phase)
0.6546	Remote Similarity	NPD6621	Clinical (unspecified phase)
0.6534	Remote Similarity	NPD6396	Clinical (unspecified phase)
0.6534	Remote Similarity	NPD4201	Clinical (unspecified phase)
0.6534	Remote Similarity	NPD6395	Phase 2
0.6529	Remote Similarity	NPD2241	Approved
0.6509	Remote Similarity	NPD2578	Phase 3
0.6505	Remote Similarity	NPD6654	Clinical (unspecified phase)
0.6505	Remote Similarity	NPD6878	Phase 2
0.6505	Remote Similarity	NPD6879	Phase 2
0.6497	Remote Similarity	NPD1769	Discontinued
0.6474	Remote Similarity	NPD4644	Clinical (unspecified phase)
0.6474	Remote Similarity	NPD8103	Clinical (unspecified phase)
0.6474	Remote Similarity	NPD4515	Suspended
0.6458	Remote Similarity	NPD5042	Phase 1
0.6458	Remote Similarity	NPD3785	Clinical (unspecified phase)
0.6455	Remote Similarity	NPD6021	Clinical (unspecified phase)
0.645	Remote Similarity	NPD3069	Approved
0.645	Remote Similarity	NPD521	Clinical (unspecified phase)
0.6443	Remote Similarity	NPD1065	Approved
0.6443	Remote Similarity	NPD1064	Approved
0.644	Remote Similarity	NPD7444	Clinical (unspecified phase)
0.6432	Remote Similarity	NPD6669	Phase 2
0.6429	Remote Similarity	NPD7890	Discontinued
0.6425	Remote Similarity	NPD6063	Approved
0.6416	Remote Similarity	NPD7441	Clinical (unspecified phase)
0.6413	Remote Similarity	NPD5858	Discontinued
0.6412	Remote Similarity	NPD1908	Phase 2
0.6412	Remote Similarity	NPD6414	Clinical (unspecified phase)
0.64	Remote Similarity	NPD8330	Clinical (unspecified phase)
0.6396	Remote Similarity	NPD6874	Approved
0.6393	Remote Similarity	NPD5186	Approved
0.6393	Remote Similarity	NPD5183	Approved
0.6387	Remote Similarity	NPD6793	Clinical (unspecified phase)
0.6378	Remote Similarity	NPD7238	Clinical (unspecified phase)
0.6374	Remote Similarity	NPD2162	Clinical (unspecified phase)
0.6374	Remote Similarity	NPD2904	Discontinued
0.6364	Remote Similarity	NPD5542	Phase 2
0.6359	Remote Similarity	NPD4897	Phase 2
0.6359	Remote Similarity	NPD3824	Phase 1
0.6359	Remote Similarity	NPD7256	Discontinued
0.6354	Remote Similarity	NPD4334	Discontinued
0.6343	Remote Similarity	NPD2737	Clinical (unspecified phase)
0.6337	Remote Similarity	NPD7584	Approved
0.6337	Remote Similarity	NPD7583	Approved
0.6331	Remote Similarity	NPD822	Approved
0.6331	Remote Similarity	NPD3170	Approved
0.6328	Remote Similarity	NPD4121	Phase 3
0.6328	Remote Similarity	NPD4120	Approved
0.6325	Remote Similarity	NPD1594	Phase 3
0.6325	Remote Similarity	NPD1595	Approved
0.6324	Remote Similarity	NPD6365	Clinical (unspecified phase)
0.6319	Remote Similarity	NPD7247	Discontinued
0.6316	Remote Similarity	NPD4598	Approved
0.6316	Remote Similarity	NPD4597	Approved
0.6313	Remote Similarity	NPD7735	Clinical (unspecified phase)
0.631	Remote Similarity	NPD5334	Clinical (unspecified phase)
0.6308	Remote Similarity	NPD5150	Phase 2
0.6305	Remote Similarity	NPD7585	Approved
0.6302	Remote Similarity	NPD6891	Phase 2
0.6296	Remote Similarity	NPD6320	Approved
0.6294	Remote Similarity	NPD6206	Phase 1
0.6292	Remote Similarity	NPD5741	Approved
0.6292	Remote Similarity	NPD5742	Approved
0.6292	Remote Similarity	NPD5743	Approved
0.6291	Remote Similarity	NPD7186	Phase 3
0.629	Remote Similarity	NPD6316	Clinical (unspecified phase)
0.6289	Remote Similarity	NPD5723	Approved
0.6278	Remote Similarity	NPD4485	Approved
0.6278	Remote Similarity	NPD6060	Clinical (unspecified phase)
0.6278	Remote Similarity	NPD5294	Clinical (unspecified phase)
0.6278	Remote Similarity	NPD3388	Phase 1
0.6272	Remote Similarity	NPD6636	Phase 3
0.6264	Remote Similarity	NPD6533	Clinical (unspecified phase)
0.6263	Remote Similarity	NPD6261	Phase 3
0.6257	Remote Similarity	NPD7266	Discontinued
0.6256	Remote Similarity	NPD7569	Approved
0.6256	Remote Similarity	NPD7570	Approved
0.625	Remote Similarity	NPD5444	Phase 1
0.625	Remote Similarity	NPD7476	Discontinued
0.625	Remote Similarity	NPD6457	Approved
0.6242	Remote Similarity	NPD4365	Phase 2
0.6237	Remote Similarity	NPD4428	Discontinued
0.6237	Remote Similarity	NPD3321	Discontinued
0.6237	Remote Similarity	NPD7630	Phase 3
0.6237	Remote Similarity	NPD7628	Phase 3
0.6237	Remote Similarity	NPD7629	Clinical (unspecified phase)
0.6236	Remote Similarity	NPD6357	Discontinued
0.6231	Remote Similarity	NPD3800	Clinical (unspecified phase)
0.6231	Remote Similarity	NPD6249	Phase 2
0.6231	Remote Similarity	NPD1880	Phase 3
0.6231	Remote Similarity	NPD6248	Phase 2
0.6229	Remote Similarity	NPD1802	Approved
0.6229	Remote Similarity	NPD1801	Approved
0.6226	Remote Similarity	NPD1306	Clinical (unspecified phase)
0.6224	Remote Similarity	NPD7262	Phase 1
0.6223	Remote Similarity	NPD3449	Discontinued
0.622	Remote Similarity	NPD8326	Phase 3
0.622	Remote Similarity	NPD8325	Phase 3
0.622	Remote Similarity	NPD8327	Clinical (unspecified phase)
0.6211	Remote Similarity	NPD7149	Clinical (unspecified phase)
0.6209	Remote Similarity	NPD3437	Discontinued
0.6205	Remote Similarity	NPD6659	Phase 2
0.6205	Remote Similarity	NPD3808	Clinical (unspecified phase)
0.6204	Remote Similarity	NPD7589	Clinical (unspecified phase)
0.6203	Remote Similarity	NPD5919	Clinical (unspecified phase)
0.6198	Remote Similarity	NPD8167	Discontinued
0.6196	Remote Similarity	NPD5823	Approved
0.6196	Remote Similarity	NPD2041	Clinical (unspecified phase)
0.6196	Remote Similarity	NPD2042	Clinical (unspecified phase)
0.6193	Remote Similarity	NPD5941	Approved
0.6193	Remote Similarity	NPD5942	Approved
0.6193	Remote Similarity	NPD2335	Discontinued
0.6188	Remote Similarity	NPD2842	Clinical (unspecified phase)
0.6186	Remote Similarity	NPD5620	Clinical (unspecified phase)
0.6185	Remote Similarity	NPD2820	Phase 3
0.6185	Remote Similarity	NPD6301	Phase 2
0.6181	Remote Similarity	NPD5071	Phase 2
0.6179	Remote Similarity	NPD7805	Phase 3
0.6179	Remote Similarity	NPD5506	Approved
0.6179	Remote Similarity	NPD5507	Approved
0.6176	Remote Similarity	NPD3864	Clinical (unspecified phase)
0.6176	Remote Similarity	NPD7043	Discontinued
0.6173	Remote Similarity	NPD4315	Phase 2
0.6173	Remote Similarity	NPD5214	Phase 2
0.6171	Remote Similarity	NPD3141	Discontinued
0.617	Remote Similarity	NPD5603	Clinical (unspecified phase)
0.617	Remote Similarity	NPD4020	Clinical (unspecified phase)
0.6164	Remote Similarity	NPD1668	Clinical (unspecified phase)
0.6163	Remote Similarity	NPD3656	Approved
0.6163	Remote Similarity	NPD2093	Discontinued
0.6162	Remote Similarity	NPD7126	Discontinued
0.6158	Remote Similarity	NPD4513	Discontinued
0.6158	Remote Similarity	NPD7891	Discontinued
0.6154	Remote Similarity	NPD6136	Phase 2
0.6154	Remote Similarity	NPD5896	Clinical (unspecified phase)
0.6154	Remote Similarity	NPD5181	Approved
0.6154	Remote Similarity	NPD1012	Discontinued
0.6154	Remote Similarity	NPD5179	Approved
0.6154	Remote Similarity	NPD7600	Phase 2
0.6154	Remote Similarity	NPD5180	Approved
0.615	Remote Similarity	NPD5078	Clinical (unspecified phase)
0.6147	Remote Similarity	NPD7796	Approved
0.6147	Remote Similarity	NPD7797	Approved
0.6141	Remote Similarity	NPD7035	Approved
0.6141	Remote Similarity	NPD3363	Clinical (unspecified phase)
0.6141	Remote Similarity	NPD7036	Phase 3
0.614	Remote Similarity	NPD7224	Discontinued
0.614	Remote Similarity	NPD7223	Discontinued
0.6136	Remote Similarity	NPD7794	Clinical (unspecified phase)
0.6134	Remote Similarity	NPD6484	Approved
0.6134	Remote Similarity	NPD6483	Approved
0.6134	Remote Similarity	NPD4951	Discontinued
0.6133	Remote Similarity	NPD5715	Clinical (unspecified phase)
0.6133	Remote Similarity	NPD6886	Approved
0.6133	Remote Similarity	NPD6885	Approved
0.6132	Remote Similarity	NPD8479	Phase 2
0.6129	Remote Similarity	NPD969	Suspended
0.6127	Remote Similarity	NPD2365	Approved
0.6121	Remote Similarity	NPD3912	Discontinued
0.6119	Remote Similarity	NPD6519	Phase 2
0.6118	Remote Similarity	NPD2492	Phase 1
0.6117	Remote Similarity	NPD7449	Clinical (unspecified phase)
0.6114	Remote Similarity	NPD6622	Phase 1
0.6114	Remote Similarity	NPD5595	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