NPASS Compound

Structure

NPC475609 OpenBabel07101719132D 44 48 0 0 1 0 0 0 0 0999 V2000 -5.5415 7.7007 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0754 6.3404 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5649 4.6853 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0544 3.0302 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5352 -2.5181 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4538 2.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.7641 6.7258 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6831 1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8171 1.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6831 0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.6969 -0.1171 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1307 -1.0181 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9890 -1.8271 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7219 -2.1416 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0310 6.0456 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5205 4.3905 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -4.0099 2.7354 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -2.9401 -1.5181 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9511 1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8171 -0.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7219 0.1054 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.9401 -0.5181 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.9511 0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.2535 5.0707 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.7430 3.4156 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -0.0000 1.6180 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.2325 1.7605 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4067 -0.9135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5823 0.7045 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4013 -1.0181 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.5878 0.8090 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.9890 -0.2091 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -0.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 1.8171 -1.1910 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.2091 4.7760 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.6986 3.1209 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.3090 2.5691 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.1880 1.4658 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.1810 -1.7226 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.1701 1.5135 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.6969 -1.9190 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4994 1.0803 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.5352 -1.5181 0.0000 S 0 0 0 0 0 0 0 0 0 0 0 0 -1.4538 1.3090 0.0000 S 0 0 0 0 0 0 0 0 0 0 0 0 1 7 1 0 0 0 0 2 15 1 0 0 0 0 3 16 1 0 0 0 0 4 17 1 0 0 0 0 5 43 1 0 0 0 0 6 44 1 0 0 0 0 7 15 2 0 0 0 0 8 9 2 0 0 0 0 8 10 1 0 0 0 0 9 19 1 0 0 0 0 10 20 2 0 0 0 0 11 12 2 0 0 0 0 11 21 1 0 0 0 0 12 41 1 0 0 0 0 13 18 1 0 0 0 0 13 30 1 0 0 0 0 14 18 2 0 0 0 0 14 41 1 0 0 0 0 15 24 1 0 0 0 0 16 24 1 0 0 0 0 16 25 1 0 0 0 0 17 25 1 0 0 0 0 17 27 1 0 0 0 0 19 23 2 0 0 0 0 19 26 1 0 0 0 0 20 23 1 0 0 0 0 20 34 1 0 0 0 0 21 22 1 0 0 0 0 21 42 1 6 0 0 0 22 18 1 1 0 0 0 22 32 1 0 0 0 0 23 33 1 0 0 0 0 24 35 2 0 0 0 0 25 36 1 0 0 0 0 26 31 1 6 0 0 0 26 37 1 0 0 0 0 27 38 2 0 0 0 0 27 42 1 0 0 0 0 28 30 1 0 0 0 0 28 33 1 0 0 0 0 28 39 2 0 0 0 0 29 31 1 0 0 0 0 29 32 1 0 0 0 0 29 40 2 0 0 0 0 30 32 1 0 0 0 0 30 43 1 1 0 0 0 31 33 1 0 0 0 0 31 44 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	644.19
Volume:	613.709
LogP:	1.984
LogD:	2.084
LogS:	-3.518
# Rotatable Bonds:	9
TPSA:	153.91
# H-Bond Aceptor:	11
# H-Bond Donor:	3
# Rings:	5
# Heavy Atoms:	13

MedChem Properties

QED Drug-Likeness Score:	0.283
Synthetic Accessibility Score:	5.936
Fsp3:	0.484
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.527
MDCK Permeability:	1.1827868547698017e-05
Pgp-inhibitor:	0.009
Pgp-substrate:	0.86
Human Intestinal Absorption (HIA):	0.45
20% Bioavailability (F20%):	0.008
30% Bioavailability (F30%):	0.279

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.029
Plasma Protein Binding (PPB):	80.03421020507812%
Volume Distribution (VD):	1.033
Pgp-substrate:	19.859050750732422%

ADMET: Metabolism

CYP1A2-inhibitor:	0.014
CYP1A2-substrate:	0.085
CYP2C19-inhibitor:	0.677
CYP2C19-substrate:	0.842
CYP2C9-inhibitor:	0.931
CYP2C9-substrate:	0.116
CYP2D6-inhibitor:	0.363
CYP2D6-substrate:	0.034
CYP3A4-inhibitor:	0.916
CYP3A4-substrate:	0.972

ADMET: Excretion

Clearance (CL):	6.663
Half-life (T1/2):	0.616

ADMET: Toxicity

hERG Blockers:	0.064
Human Hepatotoxicity (H-HT):	0.31
Drug-inuced Liver Injury (DILI):	0.982
AMES Toxicity:	0.004
Rat Oral Acute Toxicity:	0.938
Maximum Recommended Daily Dose:	0.978
Skin Sensitization:	0.5
Carcinogencity:	0.962
Eye Corrosion:	0.003
Eye Irritation:	0.004
Respiratory Toxicity:	0.793

Download Data

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

Natural Product: NPC475609

Natural Product ID:	NPC475609
*Common Name:**	NUNCDQJROUUESZ-UBQWZBIISA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	NUNCDQJROUUESZ-UBQWZBIISA-N
Standard InCHI:	InChI=1S/C31H36N2O9S2/c1-7-15(2)24(35)16(3)25(36)17(4)27(38)42-21-11-12-41-14-18-13-30(43-5)28(39)33-23-19(9-8-10-20(23)34)26(37)31(33,44-6)29(40)32(30)22(18)21/h7-12,14,16-17,21-22,25-26,34,36-37H,13H2,1-6H3/b15-7+/t16?,17?,21-,22-,25?,26+,30+,31+/m0/s1
SMILES:	C/C=C(/C(=O)C(C(C(C(=O)O[C@H]1C=COC=C2[C@@H]1N1C(=O)[C@]3(SC)[C@H](O)c4c(N3C(=O)[C@@]1(C2)SC)c(O)ccc4)C)O)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL509235
PubChem CID:	16091526
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000211] Indoles and derivatives [CHEMONTID:0002013] Indolecarboxylic acids and derivatives

*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
NPO33429	menisporopsis theobromae bcc 3975	Species	n.a.	Eukaryota	n.a.	n.a.	n.a.	PMID[17067151]

☑ 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	4
MIC	1

Activity Type	# Activity
Cell Line	2
NON-MOLECULAR	1
Organism	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT91	Cell Line	KB	Homo sapiens	IC50	>	31000.0	nM	PMID[491173]
NPT639	Cell Line	NCI-H187	Homo sapiens	IC50	=	20300.0	nM	PMID[491173]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	>	31000.0	nM	PMID[491173]
NPT485	Organism	Plasmodium falciparum (isolate K1 / Thailand)	Plasmodium falciparum K1	IC50	=	2950.0	nM	PMID[491173]
NPT88	Organism	Mycobacterium tuberculosis	Mycobacterium tuberculosis	MIC	=	1240.0	nM	PMID[491173]

☑ 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 NPC475609 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	286
0.1-0.2	1409
0.2-0.3	5286
0.3-0.4	11986
0.4-0.5	16487
0.5-0.6	6282
0.6-0.7	933
0.7-0.8	26
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.8402	Intermediate Similarity	NPC302235
0.797	Intermediate Similarity	NPC166169
0.774	Intermediate Similarity	NPC218733
0.774	Intermediate Similarity	NPC132874
0.774	Intermediate Similarity	NPC265642
0.774	Intermediate Similarity	NPC138615
0.7678	Intermediate Similarity	NPC1464
0.7488	Intermediate Similarity	NPC195787
0.7488	Intermediate Similarity	NPC246140
0.7302	Intermediate Similarity	NPC469732
0.7265	Intermediate Similarity	NPC234772
0.7237	Intermediate Similarity	NPC122886
0.7217	Intermediate Similarity	NPC470485
0.7179	Intermediate Similarity	NPC475342
0.7177	Intermediate Similarity	NPC262725
0.7174	Intermediate Similarity	NPC471513
0.7123	Intermediate Similarity	NPC470483
0.7087	Intermediate Similarity	NPC477394
0.7074	Intermediate Similarity	NPC148124
0.7067	Intermediate Similarity	NPC316297
0.7067	Intermediate Similarity	NPC66191
0.7067	Intermediate Similarity	NPC314817
0.7054	Intermediate Similarity	NPC470482
0.7054	Intermediate Similarity	NPC470481
0.7044	Intermediate Similarity	NPC33507
0.7031	Intermediate Similarity	NPC99724
0.7029	Intermediate Similarity	NPC477395
0.7026	Intermediate Similarity	NPC248903
0.7018	Intermediate Similarity	NPC138830
0.7018	Intermediate Similarity	NPC222046
0.6983	Remote Similarity	NPC26928
0.6966	Remote Similarity	NPC477397
0.6953	Remote Similarity	NPC473458
0.6943	Remote Similarity	NPC288110
0.6912	Remote Similarity	NPC472114
0.6912	Remote Similarity	NPC472115
0.69	Remote Similarity	NPC77777
0.6892	Remote Similarity	NPC470484
0.6881	Remote Similarity	NPC474058
0.6875	Remote Similarity	NPC330683
0.6875	Remote Similarity	NPC329567
0.6864	Remote Similarity	NPC67904
0.6852	Remote Similarity	NPC204970
0.6849	Remote Similarity	NPC160113
0.6849	Remote Similarity	NPC476220
0.6849	Remote Similarity	NPC100863
0.6837	Remote Similarity	NPC5630
0.6833	Remote Similarity	NPC301501
0.6832	Remote Similarity	NPC301163
0.6828	Remote Similarity	NPC127996
0.6822	Remote Similarity	NPC329731
0.682	Remote Similarity	NPC291173
0.6792	Remote Similarity	NPC167763
0.6792	Remote Similarity	NPC470903
0.6792	Remote Similarity	NPC470112
0.6789	Remote Similarity	NPC184933
0.6789	Remote Similarity	NPC59827
0.678	Remote Similarity	NPC74216
0.6779	Remote Similarity	NPC137627
0.6773	Remote Similarity	NPC112937
0.6766	Remote Similarity	NPC266994
0.6763	Remote Similarity	NPC475123
0.6763	Remote Similarity	NPC475204
0.6762	Remote Similarity	NPC329932
0.6762	Remote Similarity	NPC477393
0.6756	Remote Similarity	NPC478075
0.675	Remote Similarity	NPC154922
0.6749	Remote Similarity	NPC469452
0.6746	Remote Similarity	NPC476227
0.6737	Remote Similarity	NPC470480
0.6736	Remote Similarity	NPC476258
0.6736	Remote Similarity	NPC304837
0.6728	Remote Similarity	NPC203628
0.6727	Remote Similarity	NPC161804
0.6726	Remote Similarity	NPC470491
0.6709	Remote Similarity	NPC478141
0.6707	Remote Similarity	NPC477396
0.6697	Remote Similarity	NPC473004
0.6697	Remote Similarity	NPC477527
0.6695	Remote Similarity	NPC10653
0.6695	Remote Similarity	NPC318525
0.6695	Remote Similarity	NPC476436
0.6682	Remote Similarity	NPC232600
0.6681	Remote Similarity	NPC223242
0.6681	Remote Similarity	NPC159815
0.668	Remote Similarity	NPC113455
0.668	Remote Similarity	NPC469451
0.6667	Remote Similarity	NPC270301
0.6667	Remote Similarity	NPC469450
0.6667	Remote Similarity	NPC4910
0.6667	Remote Similarity	NPC279871
0.6667	Remote Similarity	NPC87714
0.6653	Remote Similarity	NPC19175
0.6652	Remote Similarity	NPC90967
0.6651	Remote Similarity	NPC477526
0.6651	Remote Similarity	NPC475421
0.6638	Remote Similarity	NPC250960
0.6638	Remote Similarity	NPC126556
0.6638	Remote Similarity	NPC71539
0.6637	Remote Similarity	NPC246303
0.6636	Remote Similarity	NPC243626
0.6636	Remote Similarity	NPC314659
0.6635	Remote Similarity	NPC129624
0.6625	Remote Similarity	NPC139373
0.6623	Remote Similarity	NPC477160
0.6618	Remote Similarity	NPC52059
0.6618	Remote Similarity	NPC470069
0.6609	Remote Similarity	NPC10732
0.6608	Remote Similarity	NPC212123
0.6606	Remote Similarity	NPC174629
0.6606	Remote Similarity	NPC22689
0.6606	Remote Similarity	NPC303214
0.6606	Remote Similarity	NPC105055
0.6603	Remote Similarity	NPC40234
0.6599	Remote Similarity	NPC120239
0.6593	Remote Similarity	NPC268077
0.659	Remote Similarity	NPC21425
0.6589	Remote Similarity	NPC197335
0.6588	Remote Similarity	NPC26108
0.6584	Remote Similarity	NPC131977
0.6581	Remote Similarity	NPC219397
0.6581	Remote Similarity	NPC315804
0.6581	Remote Similarity	NPC313804
0.6573	Remote Similarity	NPC269750
0.6573	Remote Similarity	NPC194671
0.657	Remote Similarity	NPC472923
0.6557	Remote Similarity	NPC474183
0.6556	Remote Similarity	NPC476429
0.6553	Remote Similarity	NPC478007
0.6552	Remote Similarity	NPC189661
0.6549	Remote Similarity	NPC207971
0.6542	Remote Similarity	NPC470821
0.6542	Remote Similarity	NPC39822
0.654	Remote Similarity	NPC139085
0.654	Remote Similarity	NPC251212
0.654	Remote Similarity	NPC214626
0.654	Remote Similarity	NPC306804
0.6537	Remote Similarity	NPC314056
0.6532	Remote Similarity	NPC170333
0.653	Remote Similarity	NPC474059
0.6528	Remote Similarity	NPC294951
0.6525	Remote Similarity	NPC46259
0.6525	Remote Similarity	NPC128476
0.6522	Remote Similarity	NPC269449
0.652	Remote Similarity	NPC14339
0.6516	Remote Similarity	NPC314702
0.6516	Remote Similarity	NPC314083
0.6513	Remote Similarity	NPC231924
0.6511	Remote Similarity	NPC37957
0.6509	Remote Similarity	NPC155506
0.6509	Remote Similarity	NPC473006
0.6509	Remote Similarity	NPC159767
0.6509	Remote Similarity	NPC30749
0.6507	Remote Similarity	NPC107938
0.6507	Remote Similarity	NPC294516
0.6505	Remote Similarity	NPC263709
0.6505	Remote Similarity	NPC310403
0.6505	Remote Similarity	NPC97380
0.6505	Remote Similarity	NPC63210
0.6505	Remote Similarity	NPC243673
0.6505	Remote Similarity	NPC148468
0.65	Remote Similarity	NPC28510
0.65	Remote Similarity	NPC25401
0.6498	Remote Similarity	NPC251071
0.6498	Remote Similarity	NPC322621
0.6498	Remote Similarity	NPC473007
0.6498	Remote Similarity	NPC299806
0.6498	Remote Similarity	NPC478008
0.6496	Remote Similarity	NPC195636
0.6495	Remote Similarity	NPC99043
0.6495	Remote Similarity	NPC218594
0.6494	Remote Similarity	NPC313587
0.6494	Remote Similarity	NPC315893
0.6494	Remote Similarity	NPC316110
0.6493	Remote Similarity	NPC89831
0.6491	Remote Similarity	NPC477161
0.649	Remote Similarity	NPC470784
0.6489	Remote Similarity	NPC478012
0.6489	Remote Similarity	NPC478011
0.6486	Remote Similarity	NPC230313
0.6481	Remote Similarity	NPC148391
0.6479	Remote Similarity	NPC50016
0.6479	Remote Similarity	NPC476441
0.6468	Remote Similarity	NPC87391
0.6466	Remote Similarity	NPC305542
0.6466	Remote Similarity	NPC119722
0.6464	Remote Similarity	NPC314176
0.6463	Remote Similarity	NPC53344
0.6462	Remote Similarity	NPC181138
0.6462	Remote Similarity	NPC21752
0.6462	Remote Similarity	NPC293255
0.6462	Remote Similarity	NPC210415
0.6462	Remote Similarity	NPC298851
0.6462	Remote Similarity	NPC276993
0.6462	Remote Similarity	NPC478013
0.6462	Remote Similarity	NPC96901
0.6461	Remote Similarity	NPC220852
0.6456	Remote Similarity	NPC211525
0.6456	Remote Similarity	NPC153694
0.6455	Remote Similarity	NPC473298

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 NPC475609 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	175
0.1-0.2	540
0.2-0.3	744
0.3-0.4	1871
0.4-0.5	3216
0.5-0.6	2353
0.6-0.7	251
0.7-0.8	0
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
0.6963	Remote Similarity	NPD6659	Phase 2
0.6906	Remote Similarity	NPD6518	Discontinued
0.6903	Remote Similarity	NPD4494	Approved
0.6903	Remote Similarity	NPD4492	Approved
0.6901	Remote Similarity	NPD8103	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD4082	Approved
0.6875	Remote Similarity	NPD2907	Approved
0.6875	Remote Similarity	NPD2906	Approved
0.6856	Remote Similarity	NPD3940	Clinical (unspecified phase)
0.6833	Remote Similarity	NPD6321	Discontinued
0.6822	Remote Similarity	NPD6891	Phase 2
0.6816	Remote Similarity	NPD4465	Phase 2
0.6816	Remote Similarity	NPD4467	Phase 2
0.6814	Remote Similarity	NPD5860	Discontinued
0.6787	Remote Similarity	NPD6805	Discontinued
0.6726	Remote Similarity	NPD3472	Approved
0.6726	Remote Similarity	NPD4022	Approved
0.6711	Remote Similarity	NPD4493	Discontinued
0.6711	Remote Similarity	NPD1945	Phase 1
0.6695	Remote Similarity	NPD3437	Discontinued
0.6695	Remote Similarity	NPD7186	Phase 3
0.6682	Remote Similarity	NPD6238	Discontinued
0.6681	Remote Similarity	NPD3888	Discontinued
0.6667	Remote Similarity	NPD4456	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD7805	Phase 3
0.6667	Remote Similarity	NPD3372	Discontinued
0.6667	Remote Similarity	NPD3893	Discontinued
0.6652	Remote Similarity	NPD4455	Discontinued
0.6651	Remote Similarity	NPD5994	Discontinued
0.662	Remote Similarity	NPD6654	Clinical (unspecified phase)
0.661	Remote Similarity	NPD3912	Discontinued
0.6608	Remote Similarity	NPD4596	Phase 1
0.6606	Remote Similarity	NPD5113	Approved
0.6606	Remote Similarity	NPD5114	Approved
0.6606	Remote Similarity	NPD5112	Approved
0.6592	Remote Similarity	NPD6874	Approved
0.6588	Remote Similarity	NPD7449	Clinical (unspecified phase)
0.6574	Remote Similarity	NPD8463	Approved
0.6569	Remote Similarity	NPD7118	Clinical (unspecified phase)
0.6557	Remote Similarity	NPD5603	Clinical (unspecified phase)
0.6553	Remote Similarity	NPD5433	Clinical (unspecified phase)
0.6553	Remote Similarity	NPD3783	Clinical (unspecified phase)
0.6549	Remote Similarity	NPD7205	Discontinued
0.6547	Remote Similarity	NPD4668	Phase 2
0.6528	Remote Similarity	NPD7281	Phase 3
0.6528	Remote Similarity	NPD7280	Phase 3
0.6516	Remote Similarity	NPD8157	Clinical (unspecified phase)
0.6507	Remote Similarity	NPD3351	Approved
0.6507	Remote Similarity	NPD2162	Clinical (unspecified phase)
0.6496	Remote Similarity	NPD8461	Discontinued
0.6484	Remote Similarity	NPD6608	Clinical (unspecified phase)
0.6476	Remote Similarity	NPD6478	Clinical (unspecified phase)
0.6476	Remote Similarity	NPD7597	Clinical (unspecified phase)
0.6473	Remote Similarity	NPD6199	Discontinued
0.6463	Remote Similarity	NPD3350	Approved
0.6463	Remote Similarity	NPD7560	Approved
0.646	Remote Similarity	NPD7566	Clinical (unspecified phase)
0.6447	Remote Similarity	NPD5102	Clinical (unspecified phase)
0.6444	Remote Similarity	NPD7821	Clinical (unspecified phase)
0.6444	Remote Similarity	NPD7810	Phase 3
0.6444	Remote Similarity	NPD7811	Phase 3
0.6435	Remote Similarity	NPD7149	Clinical (unspecified phase)
0.6432	Remote Similarity	NPD7071	Clinical (unspecified phase)
0.6432	Remote Similarity	NPD6795	Clinical (unspecified phase)
0.6425	Remote Similarity	NPD5077	Approved
0.6425	Remote Similarity	NPD5294	Clinical (unspecified phase)
0.6425	Remote Similarity	NPD5076	Approved
0.6422	Remote Similarity	NPD6851	Approved
0.6422	Remote Similarity	NPD6853	Approved
0.642	Remote Similarity	NPD7664	Discontinued
0.6402	Remote Similarity	NPD7820	Phase 3
0.6398	Remote Similarity	NPD2680	Approved
0.6398	Remote Similarity	NPD2681	Approved
0.6396	Remote Similarity	NPD3479	Discontinued
0.6392	Remote Similarity	NPD8255	Phase 2
0.6391	Remote Similarity	NPD6973	Clinical (unspecified phase)
0.6389	Remote Similarity	NPD6879	Phase 2
0.6389	Remote Similarity	NPD6878	Phase 2
0.6383	Remote Similarity	NPD7167	Discontinued
0.6376	Remote Similarity	NPD6644	Discontinued
0.6372	Remote Similarity	NPD5312	Approved
0.6372	Remote Similarity	NPD5313	Approved
0.6371	Remote Similarity	NPD7432	Phase 2
0.6368	Remote Similarity	NPD4652	Approved
0.636	Remote Similarity	NPD8356	Approved
0.6359	Remote Similarity	NPD3684	Discontinued
0.6351	Remote Similarity	NPD6505	Approved
0.6351	Remote Similarity	NPD6504	Approved
0.6348	Remote Similarity	NPD6260	Discontinued
0.6343	Remote Similarity	NPD5484	Approved
0.6343	Remote Similarity	NPD5485	Approved
0.6343	Remote Similarity	NPD7695	Clinical (unspecified phase)
0.634	Remote Similarity	NPD4897	Phase 2
0.6337	Remote Similarity	NPD4898	Clinical (unspecified phase)
0.6333	Remote Similarity	NPD2098	Approved
0.6332	Remote Similarity	NPD7064	Clinical (unspecified phase)
0.6329	Remote Similarity	NPD7692	Discontinued
0.6327	Remote Similarity	NPD6625	Approved
0.6322	Remote Similarity	NPD8430	Approved
0.6321	Remote Similarity	NPD2017	Approved
0.6321	Remote Similarity	NPD2888	Approved
0.6321	Remote Similarity	NPD2889	Approved
0.6321	Remote Similarity	NPD2890	Approved
0.6316	Remote Similarity	NPD7600	Phase 2
0.6313	Remote Similarity	NPD6211	Clinical (unspecified phase)
0.6313	Remote Similarity	NPD6293	Clinical (unspecified phase)
0.6311	Remote Similarity	NPD5582	Discontinued
0.6309	Remote Similarity	NPD4997	Clinical (unspecified phase)
0.6306	Remote Similarity	NPD7628	Phase 3
0.6306	Remote Similarity	NPD5928	Phase 1
0.6306	Remote Similarity	NPD7630	Phase 3
0.6306	Remote Similarity	NPD7629	Clinical (unspecified phase)
0.6304	Remote Similarity	NPD3298	Approved
0.6303	Remote Similarity	NPD2899	Discontinued
0.6301	Remote Similarity	NPD7550	Clinical (unspecified phase)
0.6301	Remote Similarity	NPD7551	Clinical (unspecified phase)
0.6291	Remote Similarity	NPD5186	Approved
0.6291	Remote Similarity	NPD5183	Approved
0.629	Remote Similarity	NPD4515	Suspended
0.6281	Remote Similarity	NPD7223	Discontinued
0.6281	Remote Similarity	NPD7224	Discontinued
0.628	Remote Similarity	NPD6716	Phase 1
0.6278	Remote Similarity	NPD4370	Phase 3
0.6277	Remote Similarity	NPD7174	Clinical (unspecified phase)
0.6274	Remote Similarity	NPD5823	Approved
0.6271	Remote Similarity	NPD4679	Discontinued
0.6268	Remote Similarity	NPD7599	Phase 2
0.6267	Remote Similarity	NPD5900	Clinical (unspecified phase)
0.6262	Remote Similarity	NPD5137	Approved
0.6256	Remote Similarity	NPD3253	Clinical (unspecified phase)
0.6256	Remote Similarity	NPD6884	Clinical (unspecified phase)
0.6255	Remote Similarity	NPD3879	Approved
0.6255	Remote Similarity	NPD7412	Clinical (unspecified phase)
0.625	Remote Similarity	NPD7048	Phase 3
0.625	Remote Similarity	NPD4846	Phase 2
0.625	Remote Similarity	NPD6982	Phase 2
0.6245	Remote Similarity	NPD5025	Approved
0.6239	Remote Similarity	NPD5445	Approved
0.6239	Remote Similarity	NPD6297	Approved
0.6238	Remote Similarity	NPD2097	Approved
0.6234	Remote Similarity	NPD5055	Clinical (unspecified phase)
0.6234	Remote Similarity	NPD5496	Approved
0.6221	Remote Similarity	NPD5521	Clinical (unspecified phase)
0.6221	Remote Similarity	NPD3449	Discontinued
0.622	Remote Similarity	NPD8102	Discontinued
0.622	Remote Similarity	NPD7031	Phase 1
0.6217	Remote Similarity	NPD956	Clinical (unspecified phase)
0.6213	Remote Similarity	NPD3878	Approved
0.6211	Remote Similarity	NPD6621	Clinical (unspecified phase)
0.6211	Remote Similarity	NPD5564	Approved
0.6211	Remote Similarity	NPD7238	Clinical (unspecified phase)
0.6208	Remote Similarity	NPD3308	Approved
0.6207	Remote Similarity	NPD6551	Clinical (unspecified phase)
0.6207	Remote Similarity	NPD8161	Suspended
0.6204	Remote Similarity	NPD4981	Phase 2
0.6204	Remote Similarity	NPD7589	Clinical (unspecified phase)
0.6195	Remote Similarity	NPD5941	Approved
0.6195	Remote Similarity	NPD5942	Approved
0.619	Remote Similarity	NPD6060	Clinical (unspecified phase)
0.619	Remote Similarity	NPD3802	Phase 3
0.6189	Remote Similarity	NPD4086	Phase 1
0.6188	Remote Similarity	NPD5852	Approved
0.6188	Remote Similarity	NPD5265	Approved
0.6188	Remote Similarity	NPD5851	Approved
0.6188	Remote Similarity	NPD5264	Approved
0.6186	Remote Similarity	NPD7178	Clinical (unspecified phase)
0.6184	Remote Similarity	NPD4420	Approved
0.6184	Remote Similarity	NPD5071	Phase 2
0.6183	Remote Similarity	NPD5506	Approved
0.6183	Remote Similarity	NPD5507	Approved
0.6181	Remote Similarity	NPD2569	Approved
0.6181	Remote Similarity	NPD2567	Approved
0.618	Remote Similarity	NPD7043	Discontinued
0.618	Remote Similarity	NPD5514	Discontinued
0.6179	Remote Similarity	NPD7284	Clinical (unspecified phase)
0.6176	Remote Similarity	NPD2433	Clinical (unspecified phase)
0.617	Remote Similarity	NPD4900	Clinical (unspecified phase)
0.6168	Remote Similarity	NPD7126	Discontinued
0.6167	Remote Similarity	NPD3307	Approved
0.6164	Remote Similarity	NPD1294	Discontinued
0.6163	Remote Similarity	NPD8492	Approved
0.616	Remote Similarity	NPD7677	Discontinued
0.6157	Remote Similarity	NPD6824	Clinical (unspecified phase)
0.6157	Remote Similarity	NPD3271	Approved
0.6157	Remote Similarity	NPD3275	Approved
0.6157	Remote Similarity	NPD3297	Approved
0.615	Remote Similarity	NPD5610	Approved
0.6148	Remote Similarity	NPD7603	Discontinued
0.6147	Remote Similarity	NPD5005	Approved
0.6147	Remote Similarity	NPD5006	Approved
0.6147	Remote Similarity	NPD3050	Clinical (unspecified phase)
0.6147	Remote Similarity	NPD5600	Discontinued
0.6145	Remote Similarity	NPD3006	Discontinued
0.6144	Remote Similarity	NPD7272	Discontinued
0.6143	Remote Similarity	NPD1769	Discontinued
0.6141	Remote Similarity	NPD7858	Clinical (unspecified phase)
0.6135	Remote Similarity	NPD1670	Discontinued
0.6135	Remote Similarity	NPD8330	Clinical (unspecified phase)
0.6133	Remote Similarity	NPD6475	Phase 2
0.613	Remote Similarity	NPD6519	Phase 2

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