NPASS Compound

Structure

NPC470874 OpenBabel07101719512D 42 50 0 0 1 0 0 0 0 0999 V2000 -2.6356 1.1849 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7386 -0.0396 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8240 1.4272 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0377 -1.0637 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1206 -2.0115 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3431 -3.9871 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3232 -3.1041 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0803 -1.4552 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9561 -2.1072 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1635 -1.7653 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9360 -1.9153 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5022 -2.3061 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2702 -1.3745 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6480 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9515 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1377 -0.5931 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8336 0.2542 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8240 0.4757 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6480 -0.9515 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0420 -2.3362 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.2592 -1.1641 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9515 -0.9515 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.3688 -2.4166 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5714 -0.2024 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.8145 -1.3443 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8240 -1.4272 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.9515 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.7607 -2.1504 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2474 -2.6637 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1267 -0.3826 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.4757 -2.7270 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.6348 -3.0875 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2583 -1.6094 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9470 -2.1258 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.5132 -2.5165 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8255 -1.5548 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.1954 -2.9640 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -1.3734 0.7283 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.6274 -0.6242 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.2482 -0.9536 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.0704 -2.3106 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 2 0 0 0 0 4 34 1 0 0 0 0 5 34 1 0 0 0 0 6 35 1 0 0 0 0 8 9 2 0 0 0 0 8 19 1 0 0 0 0 9 24 1 0 0 0 0 10 13 1 0 0 0 0 10 21 1 0 0 0 0 11 12 1 0 0 0 0 12 35 1 0 0 0 0 13 37 1 0 0 0 0 14 18 1 0 0 0 0 14 19 1 0 0 0 0 16 22 2 0 0 0 0 16 25 1 0 0 0 0 18 20 1 0 0 0 0 19 27 2 0 0 0 0 20 15 1 1 0 0 0 20 28 1 0 0 0 0 21 32 1 0 0 0 0 21 36 1 1 0 0 0 22 26 1 0 0 0 0 22 37 1 0 0 0 0 23 15 1 1 0 0 0 23 28 1 0 0 0 0 23 34 1 0 0 0 0 24 29 2 0 0 0 0 24 38 1 0 0 0 0 25 31 1 0 0 0 0 25 39 1 6 0 0 0 26 11 1 6 0 0 0 26 41 1 0 0 0 0 27 29 1 0 0 0 0 28 27 1 1 0 0 0 29 30 1 0 0 0 0 30 33 2 0 0 0 0 31 17 1 6 0 0 0 31 41 1 0 0 0 0 32 30 1 6 0 0 0 32 42 1 0 0 0 0 33 36 1 0 0 0 0 33 38 1 0 0 0 0 34 42 1 0 0 0 0 35 36 1 1 0 0 0 36 7 1 1 0 0 0 37 35 1 1 0 0 0 37 40 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	567.33
Volume:	599.202
LogP:	6.794
LogD:	4.137
LogS:	-5.567
# Rotatable Bonds:	1
TPSA:	74.71
# H-Bond Aceptor:	5
# H-Bond Donor:	3
# Rings:	9
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.336
Synthetic Accessibility Score:	5.978
Fsp3:	0.622
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Rejected
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:	-5.257
MDCK Permeability:	9.774513273441698e-06
Pgp-inhibitor:	0.992
Pgp-substrate:	0.984
Human Intestinal Absorption (HIA):	0.01
20% Bioavailability (F20%):	0.772
30% Bioavailability (F30%):	0.279

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.76
Plasma Protein Binding (PPB):	88.94742584228516%
Volume Distribution (VD):	2.452
Pgp-substrate:	6.624977111816406%

ADMET: Metabolism

CYP1A2-inhibitor:	0.022
CYP1A2-substrate:	0.935
CYP2C19-inhibitor:	0.407
CYP2C19-substrate:	0.85
CYP2C9-inhibitor:	0.283
CYP2C9-substrate:	0.167
CYP2D6-inhibitor:	0.153
CYP2D6-substrate:	0.459
CYP3A4-inhibitor:	0.753
CYP3A4-substrate:	0.92

ADMET: Excretion

Clearance (CL):	5.46
Half-life (T1/2):	0.01

ADMET: Toxicity

hERG Blockers:	0.826
Human Hepatotoxicity (H-HT):	0.425
Drug-inuced Liver Injury (DILI):	0.407
AMES Toxicity:	0.013
Rat Oral Acute Toxicity:	0.991
Maximum Recommended Daily Dose:	0.977
Skin Sensitization:	0.072
Carcinogencity:	0.869
Eye Corrosion:	0.003
Eye Irritation:	0.012
Respiratory Toxicity:	0.99

Download Data

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

Natural Product: NPC470874

Natural Product ID:	NPC470874
*Common Name:**	Penitrem D
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	XOASTWITKYDKAJ-NDYNHIGJSA-N
Standard InCHI:	InChI=1S/C37H45NO4/c1-17(2)31-25(39)16-22-26(41-31)11-12-35(6)36(7)21(10-13-37(22,35)40)32-30-29-24(38-33(30)36)9-8-19-14-18(3)20-15-23(28(20)27(19)29)34(4,5)42-32/h8-9,16,20-21,23,25-26,28,31-32,38-40H,1,3,10-15H2,2,4-7H3/t20-,21+,23-,25-,26+,28+,31-,32+,35-,36-,37-/m1/s1
SMILES:	CC(=C)[C@H]1O[C@H]2CC[C@]3([C@@](C2=C[C@H]1O)(O)CC[C@@H]1[C@]3(C)c2[nH]c3c4c2[C@H]1OC(C)(C)[C@H]1[C@H]2c4c(cc3)CC(=C)[C@H]2C1)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2272677
PubChem CID:	76308902
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0001640] Naphthopyrans

*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
NPO13779	Penicillium crustosum	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12670149]
NPO13779	Penicillium crustosum	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	3
Others	7

Activity Type	# Activity
Cell Line	4
Organism	6

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT82	Cell Line	MDA-MB-231	Homo sapiens	Inhibition	=	50.0	%	PMID[492534]
NPT82	Cell Line	MDA-MB-231	Homo sapiens	IC50	=	9200.0	nM	PMID[492534]
NPT82	Cell Line	MDA-MB-231	Homo sapiens	IC50	=	29700.0	nM	PMID[492534]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	=	8300.0	nM	PMID[492534]
NPT6649	Organism	Ceratitis capitata	Ceratitis capitata	Activity	=	52.5	%	PMID[492533]
NPT6649	Organism	Ceratitis capitata	Ceratitis capitata	Activity	=	42.8	%	PMID[492533]
NPT6649	Organism	Ceratitis capitata	Ceratitis capitata	Activity	=	77.1	%	PMID[492533]
NPT6649	Organism	Ceratitis capitata	Ceratitis capitata	mortality	=	41.7	%	PMID[492533]
NPT2212	Organism	Oncopeltus fasciatus	Oncopeltus fasciatus	Survival	=	58.3	%	PMID[492533]
NPT2212	Organism	Oncopeltus fasciatus	Oncopeltus fasciatus	mortality	=	11.1	%	PMID[492533]

☑ 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 NPC470874 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	505
0.1-0.2	1783
0.2-0.3	5951
0.3-0.4	16113
0.4-0.5	13782
0.5-0.6	3355
0.6-0.7	1079
0.7-0.8	76
0.8-0.85	36
0.85-0.9	8
0.9-0.95	6
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9701	High Similarity	NPC470873
0.9507	High Similarity	NPC249342
0.9104	High Similarity	NPC188239
0.8727	High Similarity	NPC473389
0.8682	High Similarity	NPC199259
0.814	Intermediate Similarity	NPC61813
0.8084	Intermediate Similarity	NPC96131
0.7991	Intermediate Similarity	NPC473650
0.7991	Intermediate Similarity	NPC160527
0.7974	Intermediate Similarity	NPC94541
0.7974	Intermediate Similarity	NPC470843
0.7921	Intermediate Similarity	NPC34271
0.7907	Intermediate Similarity	NPC471284
0.7897	Intermediate Similarity	NPC235900
0.785	Intermediate Similarity	NPC250129
0.7848	Intermediate Similarity	NPC471634
0.7848	Intermediate Similarity	NPC473806
0.7837	Intermediate Similarity	NPC32200
0.7812	Intermediate Similarity	NPC282033
0.7804	Intermediate Similarity	NPC475165
0.7763	Intermediate Similarity	NPC242446
0.7763	Intermediate Similarity	NPC475476
0.7713	Intermediate Similarity	NPC79107
0.7713	Intermediate Similarity	NPC475424
0.77	Intermediate Similarity	NPC187456
0.7696	Intermediate Similarity	NPC119700
0.7692	Intermediate Similarity	NPC231342
0.7635	Intermediate Similarity	NPC165201
0.7624	Intermediate Similarity	NPC302191
0.7608	Intermediate Similarity	NPC205403
0.758	Intermediate Similarity	NPC97388
0.7574	Intermediate Similarity	NPC198339
0.7547	Intermediate Similarity	NPC475151
0.7534	Intermediate Similarity	NPC473547
0.7523	Intermediate Similarity	NPC477135
0.7477	Intermediate Similarity	NPC123019
0.7453	Intermediate Similarity	NPC473747
0.7373	Intermediate Similarity	NPC18661
0.7353	Intermediate Similarity	NPC6093
0.7352	Intermediate Similarity	NPC284102
0.735	Intermediate Similarity	NPC154293
0.7327	Intermediate Similarity	NPC97525
0.7269	Intermediate Similarity	NPC41318
0.7269	Intermediate Similarity	NPC469312
0.726	Intermediate Similarity	NPC476319
0.7204	Intermediate Similarity	NPC206967
0.7184	Intermediate Similarity	NPC270009
0.7161	Intermediate Similarity	NPC473565
0.7156	Intermediate Similarity	NPC46413
0.7149	Intermediate Similarity	NPC61637
0.7081	Intermediate Similarity	NPC472444
0.7069	Intermediate Similarity	NPC183426
0.6991	Remote Similarity	NPC85066
0.6991	Remote Similarity	NPC181502
0.699	Remote Similarity	NPC34508
0.6982	Remote Similarity	NPC476106
0.6979	Remote Similarity	NPC477531
0.6966	Remote Similarity	NPC252251
0.6947	Remote Similarity	NPC48353
0.6938	Remote Similarity	NPC472443
0.6936	Remote Similarity	NPC209174
0.6919	Remote Similarity	NPC19679
0.69	Remote Similarity	NPC314552
0.6875	Remote Similarity	NPC193777
0.6864	Remote Similarity	NPC476175
0.6853	Remote Similarity	NPC477532
0.6846	Remote Similarity	NPC471782
0.6846	Remote Similarity	NPC471583
0.6822	Remote Similarity	NPC99428
0.6818	Remote Similarity	NPC37473
0.6815	Remote Similarity	NPC131273
0.6815	Remote Similarity	NPC473441
0.6814	Remote Similarity	NPC201697
0.6805	Remote Similarity	NPC278540
0.6794	Remote Similarity	NPC472586
0.6792	Remote Similarity	NPC192270
0.6776	Remote Similarity	NPC473189
0.6773	Remote Similarity	NPC153042
0.6771	Remote Similarity	NPC475085
0.6771	Remote Similarity	NPC291535
0.6771	Remote Similarity	NPC475112
0.6769	Remote Similarity	NPC475602
0.6765	Remote Similarity	NPC473320
0.6759	Remote Similarity	NPC246700
0.675	Remote Similarity	NPC277351
0.6745	Remote Similarity	NPC300688
0.673	Remote Similarity	NPC151939
0.6728	Remote Similarity	NPC469497
0.6728	Remote Similarity	NPC106833
0.6726	Remote Similarity	NPC476044
0.6726	Remote Similarity	NPC267423
0.671	Remote Similarity	NPC204491
0.6709	Remote Similarity	NPC57690
0.67	Remote Similarity	NPC184476
0.6697	Remote Similarity	NPC243834
0.6697	Remote Similarity	NPC70956
0.6696	Remote Similarity	NPC127677
0.6695	Remote Similarity	NPC141428
0.6695	Remote Similarity	NPC245756
0.6682	Remote Similarity	NPC128751
0.6667	Remote Similarity	NPC162484
0.6667	Remote Similarity	NPC311451
0.6667	Remote Similarity	NPC72211
0.6652	Remote Similarity	NPC46225
0.6651	Remote Similarity	NPC280548
0.6651	Remote Similarity	NPC293472
0.6639	Remote Similarity	NPC476492
0.6638	Remote Similarity	NPC30570
0.6638	Remote Similarity	NPC475422
0.6624	Remote Similarity	NPC235885
0.6623	Remote Similarity	NPC478074
0.6618	Remote Similarity	NPC472587
0.6613	Remote Similarity	NPC107836
0.6609	Remote Similarity	NPC249428
0.6609	Remote Similarity	NPC162812
0.6606	Remote Similarity	NPC205934
0.6606	Remote Similarity	NPC195314
0.6606	Remote Similarity	NPC43787
0.6599	Remote Similarity	NPC284141
0.6597	Remote Similarity	NPC112547
0.6581	Remote Similarity	NPC469594
0.658	Remote Similarity	NPC151976
0.658	Remote Similarity	NPC292517
0.6579	Remote Similarity	NPC474905
0.6577	Remote Similarity	NPC70259
0.6575	Remote Similarity	NPC95783
0.6574	Remote Similarity	NPC190007
0.657	Remote Similarity	NPC473182
0.6569	Remote Similarity	NPC470126
0.6569	Remote Similarity	NPC471458
0.6567	Remote Similarity	NPC477907
0.6567	Remote Similarity	NPC203614
0.6567	Remote Similarity	NPC42678
0.6567	Remote Similarity	NPC477909
0.6565	Remote Similarity	NPC234999
0.6561	Remote Similarity	NPC279401
0.6561	Remote Similarity	NPC79293
0.6561	Remote Similarity	NPC472589
0.6556	Remote Similarity	NPC290529
0.6555	Remote Similarity	NPC98371
0.6555	Remote Similarity	NPC475137
0.6555	Remote Similarity	NPC475498
0.6555	Remote Similarity	NPC313884
0.6553	Remote Similarity	NPC216428
0.655	Remote Similarity	NPC258062
0.655	Remote Similarity	NPC470280
0.655	Remote Similarity	NPC87755
0.6544	Remote Similarity	NPC94943
0.6542	Remote Similarity	NPC471190
0.6542	Remote Similarity	NPC470486
0.6542	Remote Similarity	NPC475644
0.6542	Remote Similarity	NPC471977
0.654	Remote Similarity	NPC126492
0.6537	Remote Similarity	NPC204303
0.6529	Remote Similarity	NPC30456
0.6528	Remote Similarity	NPC472108
0.6528	Remote Similarity	NPC139291
0.6527	Remote Similarity	NPC267926
0.6527	Remote Similarity	NPC202503
0.6525	Remote Similarity	NPC477533
0.6522	Remote Similarity	NPC477548
0.6522	Remote Similarity	NPC472550
0.6522	Remote Similarity	NPC304179
0.6522	Remote Similarity	NPC48042
0.652	Remote Similarity	NPC471564
0.652	Remote Similarity	NPC98715
0.6513	Remote Similarity	NPC147446
0.6513	Remote Similarity	NPC266192
0.6513	Remote Similarity	NPC76565
0.6511	Remote Similarity	NPC62367
0.6509	Remote Similarity	NPC472553
0.6509	Remote Similarity	NPC473180
0.6509	Remote Similarity	NPC475778
0.6509	Remote Similarity	NPC313791
0.6507	Remote Similarity	NPC225821
0.6507	Remote Similarity	NPC470508
0.65	Remote Similarity	NPC87152
0.65	Remote Similarity	NPC475631
0.65	Remote Similarity	NPC476110
0.65	Remote Similarity	NPC475600
0.65	Remote Similarity	NPC110151
0.6498	Remote Similarity	NPC2395
0.6494	Remote Similarity	NPC199667
0.6494	Remote Similarity	NPC476516
0.6494	Remote Similarity	NPC126066
0.6489	Remote Similarity	NPC128823
0.6488	Remote Similarity	NPC475303
0.6488	Remote Similarity	NPC475596
0.6485	Remote Similarity	NPC473850
0.6484	Remote Similarity	NPC473177
0.6482	Remote Similarity	NPC472588
0.6481	Remote Similarity	NPC314394
0.6478	Remote Similarity	NPC217554
0.6478	Remote Similarity	NPC63041
0.6478	Remote Similarity	NPC470931
0.6475	Remote Similarity	NPC170751
0.6473	Remote Similarity	NPC253580
0.6473	Remote Similarity	NPC232130
0.6473	Remote Similarity	NPC475362
0.6471	Remote Similarity	NPC122463

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 NPC470874 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	299
0.1-0.2	590
0.2-0.3	706
0.3-0.4	2292
0.4-0.5	3462
0.5-0.6	1525
0.6-0.7	274
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
0.69	Remote Similarity	NPD5164	Discontinued
0.687	Remote Similarity	NPD6503	Clinical (unspecified phase)
0.6639	Remote Similarity	NPD6977	Clinical (unspecified phase)
0.6639	Remote Similarity	NPD6978	Phase 2
0.6624	Remote Similarity	NPD6455	Phase 3
0.6622	Remote Similarity	NPD5003	Discontinued
0.6621	Remote Similarity	NPD5913	Phase 3
0.6621	Remote Similarity	NPD5912	Clinical (unspecified phase)
0.6615	Remote Similarity	NPD6773	Clinical (unspecified phase)
0.6609	Remote Similarity	NPD5939	Approved
0.6609	Remote Similarity	NPD5936	Approved
0.6605	Remote Similarity	NPD5596	Phase 2
0.6596	Remote Similarity	NPD6717	Clinical (unspecified phase)
0.6571	Remote Similarity	NPD1326	Approved
0.6571	Remote Similarity	NPD1325	Approved
0.6555	Remote Similarity	NPD6976	Clinical (unspecified phase)
0.6522	Remote Similarity	NPD2125	Clinical (unspecified phase)
0.6504	Remote Similarity	NPD4511	Phase 1
0.6471	Remote Similarity	NPD6995	Phase 1
0.6466	Remote Similarity	NPD4502	Phase 2
0.6463	Remote Similarity	NPD3003	Approved
0.6447	Remote Similarity	NPD2920	Discontinued
0.6444	Remote Similarity	NPD7889	Clinical (unspecified phase)
0.6441	Remote Similarity	NPD8109	Clinical (unspecified phase)
0.6434	Remote Similarity	NPD7558	Phase 2
0.6429	Remote Similarity	NPD5744	Clinical (unspecified phase)
0.6425	Remote Similarity	NPD2565	Phase 2
0.6425	Remote Similarity	NPD2564	Approved
0.6415	Remote Similarity	NPD8429	Approved
0.6415	Remote Similarity	NPD7474	Suspended
0.6415	Remote Similarity	NPD8428	Approved
0.6415	Remote Similarity	NPD8427	Approved
0.6395	Remote Similarity	NPD6220	Phase 3
0.6389	Remote Similarity	NPD4079	Approved
0.6389	Remote Similarity	NPD4076	Approved
0.6384	Remote Similarity	NPD6491	Clinical (unspecified phase)
0.6383	Remote Similarity	NPD5902	Approved
0.6383	Remote Similarity	NPD5903	Approved
0.6376	Remote Similarity	NPD5522	Clinical (unspecified phase)
0.6374	Remote Similarity	NPD8364	Approved
0.6374	Remote Similarity	NPD8363	Approved
0.6372	Remote Similarity	NPD2380	Approved
0.6372	Remote Similarity	NPD2381	Approved
0.6372	Remote Similarity	NPD2382	Approved
0.6364	Remote Similarity	NPD6290	Phase 2
0.6355	Remote Similarity	NPD7418	Discontinued
0.6351	Remote Similarity	NPD6281	Approved
0.6344	Remote Similarity	NPD2175	Phase 3
0.6344	Remote Similarity	NPD2176	Approved
0.6344	Remote Similarity	NPD2177	Approved
0.6343	Remote Similarity	NPD3506	Approved
0.6343	Remote Similarity	NPD3505	Approved
0.6326	Remote Similarity	NPD8365	Clinical (unspecified phase)
0.6323	Remote Similarity	NPD6630	Clinical (unspecified phase)
0.632	Remote Similarity	NPD8425	Approved
0.632	Remote Similarity	NPD8426	Approved
0.6318	Remote Similarity	NPD1592	Phase 3
0.631	Remote Similarity	NPD8468	Phase 2
0.6303	Remote Similarity	NPD5138	Approved
0.6303	Remote Similarity	NPD5140	Approved
0.6292	Remote Similarity	NPD8467	Approved
0.6292	Remote Similarity	NPD8466	Approved
0.6292	Remote Similarity	NPD8465	Approved
0.6287	Remote Similarity	NPD5612	Discontinued
0.6273	Remote Similarity	NPD5083	Clinical (unspecified phase)
0.6272	Remote Similarity	NPD1768	Approved
0.6266	Remote Similarity	NPD7947	Clinical (unspecified phase)
0.6256	Remote Similarity	NPD3038	Discontinued
0.6255	Remote Similarity	NPD5067	Phase 2
0.6255	Remote Similarity	NPD5066	Phase 2
0.6245	Remote Similarity	NPD4601	Approved
0.6245	Remote Similarity	NPD4600	Approved
0.6245	Remote Similarity	NPD7707	Approved
0.6245	Remote Similarity	NPD7073	Clinical (unspecified phase)
0.6239	Remote Similarity	NPD5834	Phase 3
0.6239	Remote Similarity	NPD5835	Phase 3
0.6235	Remote Similarity	NPD6494	Phase 2
0.6234	Remote Similarity	NPD6985	Discontinued
0.6232	Remote Similarity	NPD6158	Phase 2
0.6232	Remote Similarity	NPD6476	Clinical (unspecified phase)
0.6224	Remote Similarity	NPD5507	Approved
0.6224	Remote Similarity	NPD5506	Approved
0.622	Remote Similarity	NPD6026	Approved
0.622	Remote Similarity	NPD7688	Phase 1
0.6215	Remote Similarity	NPD5021	Discontinued
0.6203	Remote Similarity	NPD8094	Discontinued
0.6201	Remote Similarity	NPD8395	Approved
0.6201	Remote Similarity	NPD4118	Clinical (unspecified phase)
0.6201	Remote Similarity	NPD8396	Approved
0.6199	Remote Similarity	NPD8459	Approved
0.6199	Remote Similarity	NPD8460	Approved
0.6198	Remote Similarity	NPD6160	Clinical (unspecified phase)
0.6197	Remote Similarity	NPD7671	Approved
0.6197	Remote Similarity	NPD7672	Approved
0.6192	Remote Similarity	NPD7955	Approved
0.6192	Remote Similarity	NPD7956	Approved
0.619	Remote Similarity	NPD4670	Clinical (unspecified phase)
0.619	Remote Similarity	NPD4669	Clinical (unspecified phase)
0.619	Remote Similarity	NPD4671	Clinical (unspecified phase)
0.6188	Remote Similarity	NPD8431	Approved
0.6188	Remote Similarity	NPD4951	Discontinued
0.618	Remote Similarity	NPD5530	Phase 1
0.618	Remote Similarity	NPD4901	Clinical (unspecified phase)
0.618	Remote Similarity	NPD8403	Phase 1
0.616	Remote Similarity	NPD8093	Discontinued
0.6157	Remote Similarity	NPD7777	Approved
0.6157	Remote Similarity	NPD53	Approved
0.6157	Remote Similarity	NPD7946	Pre-registration
0.6157	Remote Similarity	NPD7778	Approved
0.6157	Remote Similarity	NPD8358	Approved
0.6154	Remote Similarity	NPD2882	Phase 1
0.6154	Remote Similarity	NPD5429	Discontinued
0.6141	Remote Similarity	NPD7194	Discontinued
0.6137	Remote Similarity	NPD4039	Approved
0.6137	Remote Similarity	NPD4037	Approved
0.6137	Remote Similarity	NPD4036	Approved
0.6137	Remote Similarity	NPD31	Approved
0.6137	Remote Similarity	NPD4034	Approved
0.6137	Remote Similarity	NPD4038	Approved
0.6137	Remote Similarity	NPD4035	Approved
0.6137	Remote Similarity	NPD32	Approved
0.6137	Remote Similarity	NPD4122	Approved
0.6137	Remote Similarity	NPD4033	Approved
0.6134	Remote Similarity	NPD3795	Approved
0.6134	Remote Similarity	NPD3794	Approved
0.6128	Remote Similarity	NPD8423	Phase 2
0.6128	Remote Similarity	NPD8399	Phase 1
0.6128	Remote Similarity	NPD5658	Approved
0.6121	Remote Similarity	NPD5721	Clinical (unspecified phase)
0.6119	Remote Similarity	NPD6641	Approved
0.6119	Remote Similarity	NPD2144	Approved
0.6119	Remote Similarity	NPD6642	Approved
0.6115	Remote Similarity	NPD8244	Phase 2
0.6114	Remote Similarity	NPD7948	Phase 1
0.6111	Remote Similarity	NPD7957	Phase 1
0.6111	Remote Similarity	NPD7958	Clinical (unspecified phase)
0.6109	Remote Similarity	NPD7867	Phase 1
0.6107	Remote Similarity	NPD7708	Approved
0.6103	Remote Similarity	NPD1685	Approved
0.6103	Remote Similarity	NPD1684	Approved
0.6102	Remote Similarity	NPD4506	Discontinued
0.6101	Remote Similarity	NPD6492	Phase 2
0.6101	Remote Similarity	NPD5065	Approved
0.6099	Remote Similarity	NPD7424	Clinical (unspecified phase)
0.6098	Remote Similarity	NPD6456	Discontinued
0.6092	Remote Similarity	NPD7069	Discontinued
0.6091	Remote Similarity	NPD8386	Phase 2
0.6085	Remote Similarity	NPD1392	Approved
0.6078	Remote Similarity	NPD7921	Approved
0.6075	Remote Similarity	NPD6635	Approved
0.6075	Remote Similarity	NPD7803	Approved
0.607	Remote Similarity	NPD6550	Discontinued
0.6065	Remote Similarity	NPD4638	Approved
0.6065	Remote Similarity	NPD4640	Approved
0.6065	Remote Similarity	NPD2844	Phase 3
0.6065	Remote Similarity	NPD4639	Approved
0.6063	Remote Similarity	NPD8464	Clinical (unspecified phase)
0.6061	Remote Similarity	NPD6248	Phase 2
0.6061	Remote Similarity	NPD6249	Phase 2
0.6055	Remote Similarity	NPD4112	Clinical (unspecified phase)
0.6053	Remote Similarity	NPD5575	Clinical (unspecified phase)
0.6053	Remote Similarity	NPD1038	Approved
0.605	Remote Similarity	NPD7927	Clinical (unspecified phase)
0.605	Remote Similarity	NPD7470	Discontinued
0.6047	Remote Similarity	NPD7769	Phase 3
0.6043	Remote Similarity	NPD7010	Phase 3
0.6043	Remote Similarity	NPD4862	Clinical (unspecified phase)
0.6042	Remote Similarity	NPD4897	Phase 2
0.6029	Remote Similarity	NPD4463	Approved
0.6029	Remote Similarity	NPD4462	Approved
0.6028	Remote Similarity	NPD972	Clinical (unspecified phase)
0.6026	Remote Similarity	NPD6590	Discontinued
0.6025	Remote Similarity	NPD3330	Phase 1
0.6025	Remote Similarity	NPD6657	Clinical (unspecified phase)
0.6018	Remote Similarity	NPD3417	Phase 1
0.6018	Remote Similarity	NPD3920	Phase 2
0.6017	Remote Similarity	NPD8160	Phase 2
0.6017	Remote Similarity	NPD7222	Phase 2
0.6009	Remote Similarity	NPD6739	Clinical (unspecified phase)
0.6009	Remote Similarity	NPD6145	Phase 1
0.6008	Remote Similarity	NPD4900	Clinical (unspecified phase)
0.6008	Remote Similarity	NPD8321	Discontinued
0.6008	Remote Similarity	NPD7710	Clinical (unspecified phase)
0.6	Remote Similarity	NPD7770	Phase 3
0.6	Remote Similarity	NPD6375	Clinical (unspecified phase)
0.6	Remote Similarity	NPD7571	Clinical (unspecified phase)
0.5992	Remote Similarity	NPD8326	Phase 3
0.5992	Remote Similarity	NPD8327	Clinical (unspecified phase)
0.5992	Remote Similarity	NPD8325	Phase 3
0.5991	Remote Similarity	NPD8063	Discontinued
0.5984	Remote Similarity	NPD5930	Phase 3
0.5984	Remote Similarity	NPD7589	Clinical (unspecified phase)
0.5983	Remote Similarity	NPD6975	Discontinued
0.5983	Remote Similarity	NPD1304	Clinical (unspecified phase)
0.5982	Remote Similarity	NPD6182	Approved
0.5982	Remote Similarity	NPD43	Approved
0.5982	Remote Similarity	NPD6183	Clinical (unspecified phase)
0.5975	Remote Similarity	NPD8112	Clinical (unspecified phase)
0.5973	Remote Similarity	NPD6159	Phase 2
0.5973	Remote Similarity	NPD5751	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