NPASS Compound

Structure

NPC268841 OpenBabel07101719512D 48 49 0 0 1 0 0 0 0 0999 V2000 -3.5829 -6.0851 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7169 -7.5851 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3748 1.2340 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6428 1.2340 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9848 2.1736 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7169 2.1736 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0765 -3.6454 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5240 -5.8512 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1069 -2.6454 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1069 -3.6454 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2409 -2.1454 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2409 -4.1454 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3748 -2.6454 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8508 -6.0851 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5088 -0.2660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5088 -4.1454 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.2105 -0.2660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7169 -6.5851 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5088 0.7340 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8508 1.6736 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.2105 -4.1454 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.3748 -3.6454 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6428 -3.6454 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.3445 -0.7660 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.8508 -5.0851 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.6428 -0.7660 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.3445 -3.6454 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.8508 0.6736 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.8356 -4.9115 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9848 -1.7057 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.6865 -2.7057 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -4.4115 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7017 -0.0000 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 0.9848 -2.7057 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -4.6865 -1.7057 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -3.7017 -4.4115 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -4.9115 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -5.2105 0.7340 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.2105 -5.1454 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.1777 -5.8512 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.9696 -1.5321 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.6713 -2.8794 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.6428 -5.1775 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.3445 0.7660 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.5240 1.4397 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 -2.8356 0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 18 1 0 0 0 0 2 18 1 0 0 0 0 3 19 1 0 0 0 0 4 19 1 0 0 0 0 5 20 1 0 0 0 0 6 20 1 0 0 0 0 8 38 1 0 0 0 0 9 10 2 0 0 0 0 9 11 1 0 0 0 0 10 12 1 0 0 0 0 11 13 2 0 0 0 0 12 22 2 0 0 0 0 13 22 1 0 0 0 0 14 18 1 0 0 0 0 15 19 1 0 0 0 0 16 22 1 0 0 0 0 17 39 1 0 0 0 0 21 7 1 6 0 0 0 21 40 1 0 0 0 0 23 16 1 1 0 0 0 23 32 1 0 0 0 0 23 35 1 0 0 0 0 24 17 1 1 0 0 0 24 33 1 0 0 0 0 24 36 1 0 0 0 0 25 14 1 1 0 0 0 25 29 1 0 0 0 0 25 38 1 0 0 0 0 26 15 1 1 0 0 0 26 30 1 0 0 0 0 26 47 1 0 0 0 0 27 21 1 1 0 0 0 27 31 1 0 0 0 0 27 37 1 0 0 0 0 28 20 1 1 0 0 0 28 34 1 0 0 0 0 28 48 1 0 0 0 0 29 37 2 3 0 0 0 29 41 1 0 0 0 0 30 35 2 3 0 0 0 30 42 1 0 0 0 0 31 36 2 3 0 0 0 31 43 1 0 0 0 0 32 38 1 0 0 0 0 32 44 2 0 0 0 0 33 45 2 0 0 0 0 33 48 1 0 0 0 0 34 46 2 0 0 0 0 34 47 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	676.37
Volume:	687.668
LogP:	2.678
LogD:	2.757
LogS:	-3.139
# Rotatable Bonds:	9
TPSA:	200.67
# H-Bond Aceptor:	14
# H-Bond Donor:	5
# Rings:	2
# Heavy Atoms:	14

MedChem Properties

QED Drug-Likeness Score:	0.229
Synthetic Accessibility Score:	5.243
Fsp3:	0.647
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:	-5.702
MDCK Permeability:	0.00012121887266403064
Pgp-inhibitor:	0.999
Pgp-substrate:	0.972
Human Intestinal Absorption (HIA):	0.018
20% Bioavailability (F20%):	0.013
30% Bioavailability (F30%):	0.966

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.059
Plasma Protein Binding (PPB):	67.14556884765625%
Volume Distribution (VD):	0.42
Pgp-substrate:	19.13686752319336%

ADMET: Metabolism

CYP1A2-inhibitor:	0.006
CYP1A2-substrate:	0.014
CYP2C19-inhibitor:	0.056
CYP2C19-substrate:	0.065
CYP2C9-inhibitor:	0.094
CYP2C9-substrate:	0.087
CYP2D6-inhibitor:	0.005
CYP2D6-substrate:	0.082
CYP3A4-inhibitor:	0.714
CYP3A4-substrate:	0.228

ADMET: Excretion

Clearance (CL):	5.034
Half-life (T1/2):	0.407

ADMET: Toxicity

hERG Blockers:	0.008
Human Hepatotoxicity (H-HT):	0.97
Drug-inuced Liver Injury (DILI):	0.877
AMES Toxicity:	0.008
Rat Oral Acute Toxicity:	0.403
Maximum Recommended Daily Dose:	0.073
Skin Sensitization:	0.049
Carcinogencity:	0.064
Eye Corrosion:	0.003
Eye Irritation:	0.006
Respiratory Toxicity:	0.029

Download Data

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

Natural Product: NPC268841

Natural Product ID:	NPC268841
*Common Name:**	Hirsutatin A
IUPAC Name:	(3S,6S,9S,12S,15S,18S)-15-benzyl-9-[(1R)-1-hydroxyethyl]-6-(hydroxymethyl)-13-methyl-12,18-bis(2-methylpropyl)-3-propan-2-yl-1,4-dioxa-7,10,13,16-tetrazacyclooctadecane-2,5,8,11,14,17-hexone
Synonyms:
Standard InCHIKey:	IKUBGKAJYBJGOR-CVSBKWFLSA-N
Standard InCHI:	InChI=1S/C34H52N4O10/c1-18(2)14-25-29(41)37-27(21(7)40)31(43)36-24(17-39)33(45)48-28(20(5)6)34(46)47-26(15-19(3)4)30(42)35-23(32(44)38(25)8)16-22-12-10-9-11-13-22/h9-13,18-21,23-28,39-40H,14-17H2,1-8H3,(H,35,42)(H,36,43)(H,37,41)/t21-,23+,24+,25+,26+,27+,28+/m1/s1
SMILES:	OC[C@@H]1N=C(O)[C@@H](N=C(O)[C@H](CC(C)C)N(C)C(=O)[C@@H](N=C([C@@H](OC(=O)[C@@H](OC1=O)C(C)C)CC(C)C)O)Cc1ccccc1)[C@H](O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL454263
PubChem CID:	11707361
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000264] Organic acids and derivatives [CHEMONTID:0001813] Peptidomimetics [CHEMONTID:0001961] Depsipeptides [CHEMONTID:0001994] Cyclic depsipeptides

*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
NPO32771	hirsutella nivea bcc 2594	Species	Ophiocordycipitaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16309324]

☑ 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
MIC	1

Activity Type	# Activity
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT88	Organism	Mycobacterium tuberculosis	Mycobacterium tuberculosis	MIC	=	50.0	ug.mL-1	PMID[524206]

☑ 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 NPC268841 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	123
0.1-0.2	662
0.2-0.3	3437
0.3-0.4	16330
0.4-0.5	18612
0.5-0.6	2699
0.6-0.7	505
0.7-0.8	246
0.8-0.85	49
0.85-0.9	28
0.9-0.95	3
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC46098
1.0	High Similarity	NPC307357
0.9248	High Similarity	NPC68865
0.8986	High Similarity	NPC201244
0.8986	High Similarity	NPC477217
0.8929	High Similarity	NPC471820
0.8929	High Similarity	NPC471821
0.8873	High Similarity	NPC162104
0.8857	High Similarity	NPC135121
0.8857	High Similarity	NPC145113
0.8759	High Similarity	NPC476133
0.8759	High Similarity	NPC470884
0.8759	High Similarity	NPC92784
0.8759	High Similarity	NPC98424
0.8759	High Similarity	NPC178662
0.8714	High Similarity	NPC5620
0.8705	High Similarity	NPC176226
0.8705	High Similarity	NPC139326
0.8699	High Similarity	NPC197743
0.8699	High Similarity	NPC297145
0.8686	High Similarity	NPC127741
0.8643	High Similarity	NPC52748
0.8633	High Similarity	NPC269398
0.8633	High Similarity	NPC263493
0.8571	High Similarity	NPC197682
0.8561	High Similarity	NPC476259
0.8551	High Similarity	NPC471265
0.8551	High Similarity	NPC471264
0.8521	High Similarity	NPC262077
0.8511	High Similarity	NPC476978
0.85	High Similarity	NPC168113
0.8472	Intermediate Similarity	NPC2501
0.8472	Intermediate Similarity	NPC129666
0.8462	Intermediate Similarity	NPC225648
0.8462	Intermediate Similarity	NPC329761
0.8451	Intermediate Similarity	NPC209509
0.8431	Intermediate Similarity	NPC196091
0.8429	Intermediate Similarity	NPC239762
0.8429	Intermediate Similarity	NPC163392
0.8403	Intermediate Similarity	NPC105717
0.837	Intermediate Similarity	NPC319766
0.831	Intermediate Similarity	NPC161069
0.8299	Intermediate Similarity	NPC122590
0.8276	Intermediate Similarity	NPC240848
0.8273	Intermediate Similarity	NPC248283
0.8244	Intermediate Similarity	NPC237420
0.8239	Intermediate Similarity	NPC469427
0.8239	Intermediate Similarity	NPC469426
0.8176	Intermediate Similarity	NPC286551
0.8168	Intermediate Similarity	NPC169328
0.8106	Intermediate Similarity	NPC310467
0.8105	Intermediate Similarity	NPC471052
0.8105	Intermediate Similarity	NPC471051
0.8105	Intermediate Similarity	NPC471053
0.8082	Intermediate Similarity	NPC138775
0.8014	Intermediate Similarity	NPC314358
0.7985	Intermediate Similarity	NPC478015
0.7985	Intermediate Similarity	NPC45777
0.7985	Intermediate Similarity	NPC478014
0.7985	Intermediate Similarity	NPC200964
0.7985	Intermediate Similarity	NPC478016
0.7985	Intermediate Similarity	NPC477061
0.7974	Intermediate Similarity	NPC471527
0.7971	Intermediate Similarity	NPC89923
0.7971	Intermediate Similarity	NPC239990
0.7971	Intermediate Similarity	NPC152850
0.7971	Intermediate Similarity	NPC71933
0.7971	Intermediate Similarity	NPC105114
0.7945	Intermediate Similarity	NPC313867
0.7945	Intermediate Similarity	NPC316008
0.7943	Intermediate Similarity	NPC287401
0.7941	Intermediate Similarity	NPC46427
0.7941	Intermediate Similarity	NPC6975
0.7908	Intermediate Similarity	NPC62104
0.7908	Intermediate Similarity	NPC1390
0.7899	Intermediate Similarity	NPC136453
0.7877	Intermediate Similarity	NPC315283
0.7877	Intermediate Similarity	NPC314388
0.7872	Intermediate Similarity	NPC246079
0.7868	Intermediate Similarity	NPC252878
0.7836	Intermediate Similarity	NPC470546
0.7823	Intermediate Similarity	NPC315266
0.7815	Intermediate Similarity	NPC473341
0.7801	Intermediate Similarity	NPC130309
0.7801	Intermediate Similarity	NPC157311
0.78	Intermediate Similarity	NPC475168
0.78	Intermediate Similarity	NPC7817
0.7794	Intermediate Similarity	NPC202521
0.7778	Intermediate Similarity	NPC43755
0.7761	Intermediate Similarity	NPC470545
0.7746	Intermediate Similarity	NPC8761
0.7746	Intermediate Similarity	NPC44805
0.7721	Intermediate Similarity	NPC476990
0.7707	Intermediate Similarity	NPC5719
0.7707	Intermediate Similarity	NPC217804
0.7707	Intermediate Similarity	NPC22883
0.7707	Intermediate Similarity	NPC210377
0.7702	Intermediate Similarity	NPC26108
0.7698	Intermediate Similarity	NPC101719
0.7687	Intermediate Similarity	NPC239357
0.7687	Intermediate Similarity	NPC470544
0.7669	Intermediate Similarity	NPC475421
0.7647	Intermediate Similarity	NPC470902
0.7626	Intermediate Similarity	NPC222466
0.7616	Intermediate Similarity	NPC283783
0.761	Intermediate Similarity	NPC63040
0.7603	Intermediate Similarity	NPC132636
0.7593	Intermediate Similarity	NPC477462
0.7593	Intermediate Similarity	NPC318930
0.7593	Intermediate Similarity	NPC317362
0.7591	Intermediate Similarity	NPC80150
0.7591	Intermediate Similarity	NPC190663
0.7571	Intermediate Similarity	NPC47667
0.7554	Intermediate Similarity	NPC175726
0.7554	Intermediate Similarity	NPC474082
0.7552	Intermediate Similarity	NPC255447
0.7547	Intermediate Similarity	NPC15068
0.7535	Intermediate Similarity	NPC473322
0.753	Intermediate Similarity	NPC167763
0.753	Intermediate Similarity	NPC470903
0.753	Intermediate Similarity	NPC470112
0.7519	Intermediate Similarity	NPC273814
0.7516	Intermediate Similarity	NPC471568
0.7516	Intermediate Similarity	NPC473693
0.75	Intermediate Similarity	NPC473502
0.7485	Intermediate Similarity	NPC473354
0.7483	Intermediate Similarity	NPC200589
0.7482	Intermediate Similarity	NPC160493
0.7468	Intermediate Similarity	NPC73655
0.7463	Intermediate Similarity	NPC35850
0.7463	Intermediate Similarity	NPC276949
0.7445	Intermediate Similarity	NPC314992
0.744	Intermediate Similarity	NPC299806
0.7429	Intermediate Similarity	NPC35996
0.7423	Intermediate Similarity	NPC273755
0.7423	Intermediate Similarity	NPC248670
0.7417	Intermediate Similarity	NPC81026
0.7413	Intermediate Similarity	NPC111428
0.7407	Intermediate Similarity	NPC33742
0.7391	Intermediate Similarity	NPC209463
0.7381	Intermediate Similarity	NPC471049
0.7381	Intermediate Similarity	NPC471048
0.7381	Intermediate Similarity	NPC471050
0.7378	Intermediate Similarity	NPC326407
0.7378	Intermediate Similarity	NPC317725
0.7378	Intermediate Similarity	NPC471165
0.7376	Intermediate Similarity	NPC476241
0.7376	Intermediate Similarity	NPC476260
0.7375	Intermediate Similarity	NPC63931
0.7351	Intermediate Similarity	NPC266741
0.7351	Intermediate Similarity	NPC322878
0.7346	Intermediate Similarity	NPC186617
0.7337	Intermediate Similarity	NPC315542
0.7333	Intermediate Similarity	NPC77905
0.7333	Intermediate Similarity	NPC50016
0.7324	Intermediate Similarity	NPC476125
0.7324	Intermediate Similarity	NPC476179
0.7317	Intermediate Similarity	NPC306804
0.7317	Intermediate Similarity	NPC137627
0.7299	Intermediate Similarity	NPC285926
0.7299	Intermediate Similarity	NPC2265
0.7299	Intermediate Similarity	NPC14672
0.7299	Intermediate Similarity	NPC315276
0.7297	Intermediate Similarity	NPC6570
0.7296	Intermediate Similarity	NPC469901
0.7292	Intermediate Similarity	NPC213969
0.7292	Intermediate Similarity	NPC165726
0.7286	Intermediate Similarity	NPC71684
0.7284	Intermediate Similarity	NPC294516
0.7284	Intermediate Similarity	NPC107938
0.7279	Intermediate Similarity	NPC141050
0.7278	Intermediate Similarity	NPC294951
0.7273	Intermediate Similarity	NPC159767
0.7273	Intermediate Similarity	NPC279871
0.7273	Intermediate Similarity	NPC155506
0.7267	Intermediate Similarity	NPC472923
0.7262	Intermediate Similarity	NPC476321
0.7259	Intermediate Similarity	NPC474584
0.7256	Intermediate Similarity	NPC89831
0.7254	Intermediate Similarity	NPC22746
0.7246	Intermediate Similarity	NPC45037
0.7241	Intermediate Similarity	NPC300315
0.7219	Intermediate Similarity	NPC471526
0.7214	Intermediate Similarity	NPC476183
0.7197	Intermediate Similarity	NPC39431
0.7195	Intermediate Similarity	NPC475204
0.7195	Intermediate Similarity	NPC40234
0.7195	Intermediate Similarity	NPC46009
0.7195	Intermediate Similarity	NPC475123
0.7172	Intermediate Similarity	NPC469666
0.7169	Intermediate Similarity	NPC158277
0.7169	Intermediate Similarity	NPC476227
0.7163	Intermediate Similarity	NPC476281
0.7163	Intermediate Similarity	NPC476184
0.7152	Intermediate Similarity	NPC230611
0.7143	Intermediate Similarity	NPC194671
0.7143	Intermediate Similarity	NPC269750
0.7069	Intermediate Similarity	NPC163961
0.7069	Intermediate Similarity	NPC473305
0.7066	Intermediate Similarity	NPC473402

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 NPC268841 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	96
0.1-0.2	297
0.2-0.3	722
0.3-0.4	2604
0.4-0.5	3687
0.5-0.6	1399
0.6-0.7	311
0.7-0.8	30
0.8-0.85	4
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8286	Intermediate Similarity	NPD8173	Phase 2
0.8286	Intermediate Similarity	NPD8172	Phase 2
0.8214	Intermediate Similarity	NPD7113	Clinical (unspecified phase)
0.8074	Intermediate Similarity	NPD2584	Suspended
0.7914	Intermediate Similarity	NPD3626	Phase 3
0.7895	Intermediate Similarity	NPD8417	Discontinued
0.7838	Intermediate Similarity	NPD8323	Discontinued
0.7727	Intermediate Similarity	NPD7749	Clinical (unspecified phase)
0.7639	Intermediate Similarity	NPD8416	Discontinued
0.7552	Intermediate Similarity	NPD4738	Phase 2
0.7517	Intermediate Similarity	NPD8265	Approved
0.7483	Intermediate Similarity	NPD6852	Discontinued
0.7445	Intermediate Similarity	NPD2218	Phase 2
0.7445	Intermediate Similarity	NPD2217	Approved
0.7386	Intermediate Similarity	NPD6088	Approved
0.7365	Intermediate Similarity	NPD6901	Phase 3
0.7343	Intermediate Similarity	NPD3604	Clinical (unspecified phase)
0.7343	Intermediate Similarity	NPD3608	Clinical (unspecified phase)
0.7343	Intermediate Similarity	NPD5339	Clinical (unspecified phase)
0.7292	Intermediate Similarity	NPD4177	Approved
0.7292	Intermediate Similarity	NPD4175	Approved
0.7241	Intermediate Similarity	NPD4125	Approved
0.723	Intermediate Similarity	NPD8643	Discontinued
0.7219	Intermediate Similarity	NPD4152	Approved
0.7219	Intermediate Similarity	NPD8076	Discontinued
0.7192	Intermediate Similarity	NPD6919	Clinical (unspecified phase)
0.7181	Intermediate Similarity	NPD6073	Approved
0.7181	Intermediate Similarity	NPD5725	Approved
0.7171	Intermediate Similarity	NPD6119	Clinical (unspecified phase)
0.7162	Intermediate Similarity	NPD6623	Phase 3
0.7153	Intermediate Similarity	NPD2585	Clinical (unspecified phase)
0.7095	Intermediate Similarity	NPD5747	Discontinued
0.707	Intermediate Similarity	NPD7613	Discontinued
0.7067	Intermediate Similarity	NPD4782	Clinical (unspecified phase)
0.7047	Intermediate Similarity	NPD4791	Clinical (unspecified phase)
0.7047	Intermediate Similarity	NPD4153	Approved
0.702	Intermediate Similarity	NPD6294	Approved
0.702	Intermediate Similarity	NPD6295	Approved
0.7014	Intermediate Similarity	NPD4677	Discontinued
0.7013	Intermediate Similarity	NPD6860	Clinical (unspecified phase)
0.7007	Intermediate Similarity	NPD7979	Clinical (unspecified phase)
0.7007	Intermediate Similarity	NPD2613	Approved
0.6993	Remote Similarity	NPD2608	Approved
0.6993	Remote Similarity	NPD2612	Approved
0.6993	Remote Similarity	NPD3131	Approved
0.6993	Remote Similarity	NPD4218	Approved
0.6993	Remote Similarity	NPD2610	Approved
0.6993	Remote Similarity	NPD3132	Approved
0.6993	Remote Similarity	NPD2609	Approved
0.6993	Remote Similarity	NPD4215	Approved
0.6993	Remote Similarity	NPD2611	Approved
0.6993	Remote Similarity	NPD4216	Approved
0.6993	Remote Similarity	NPD4217	Approved
0.698	Remote Similarity	NPD3087	Approved
0.698	Remote Similarity	NPD3615	Approved
0.698	Remote Similarity	NPD7634	Clinical (unspecified phase)
0.698	Remote Similarity	NPD3088	Approved
0.698	Remote Similarity	NPD2573	Approved
0.698	Remote Similarity	NPD2574	Discontinued
0.698	Remote Similarity	NPD2570	Approved
0.698	Remote Similarity	NPD2566	Approved
0.698	Remote Similarity	NPD2571	Approved
0.698	Remote Similarity	NPD3090	Approved
0.698	Remote Similarity	NPD4745	Approved
0.698	Remote Similarity	NPD3616	Approved
0.698	Remote Similarity	NPD2572	Clinical (unspecified phase)
0.698	Remote Similarity	NPD4746	Phase 3
0.698	Remote Similarity	NPD3089	Approved
0.698	Remote Similarity	NPD3614	Approved
0.6978	Remote Similarity	NPD1348	Approved
0.6975	Remote Similarity	NPD4557	Approved
0.6974	Remote Similarity	NPD5301	Clinical (unspecified phase)
0.6968	Remote Similarity	NPD2575	Approved
0.6959	Remote Similarity	NPD4794	Discontinued
0.6948	Remote Similarity	NPD2436	Approved
0.6948	Remote Similarity	NPD2437	Approved
0.6948	Remote Similarity	NPD6681	Discovery
0.6944	Remote Similarity	NPD3072	Approved
0.6944	Remote Similarity	NPD3073	Approved
0.6944	Remote Similarity	NPD3071	Approved
0.6943	Remote Similarity	NPD6631	Clinical (unspecified phase)
0.6933	Remote Similarity	NPD5296	Approved
0.6918	Remote Similarity	NPD2160	Approved
0.6918	Remote Similarity	NPD2625	Approved
0.6918	Remote Similarity	NPD2628	Approved
0.6918	Remote Similarity	NPD2626	Approved
0.6918	Remote Similarity	NPD2159	Approved
0.6918	Remote Similarity	NPD2627	Approved
0.6905	Remote Similarity	NPD7965	Phase 2
0.6905	Remote Similarity	NPD7964	Clinical (unspecified phase)
0.6901	Remote Similarity	NPD4504	Clinical (unspecified phase)
0.6899	Remote Similarity	NPD4185	Clinical (unspecified phase)
0.6894	Remote Similarity	NPD7267	Clinical (unspecified phase)
0.6892	Remote Similarity	NPD5202	Clinical (unspecified phase)
0.6887	Remote Similarity	NPD4686	Approved
0.6887	Remote Similarity	NPD4685	Phase 3
0.6887	Remote Similarity	NPD4684	Phase 3
0.6875	Remote Similarity	NPD4761	Approved
0.6875	Remote Similarity	NPD4706	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD4806	Approved
0.6875	Remote Similarity	NPD4807	Approved
0.6875	Remote Similarity	NPD4762	Approved
0.6867	Remote Similarity	NPD3561	Clinical (unspecified phase)
0.6861	Remote Similarity	NPD3642	Approved
0.6861	Remote Similarity	NPD3643	Approved
0.6861	Remote Similarity	NPD3644	Approved
0.6859	Remote Similarity	NPD6676	Phase 2
0.6852	Remote Similarity	NPD7118	Clinical (unspecified phase)
0.6849	Remote Similarity	NPD6792	Phase 3
0.6849	Remote Similarity	NPD5367	Discontinued
0.6839	Remote Similarity	NPD5341	Clinical (unspecified phase)
0.6835	Remote Similarity	NPD2650	Approved
0.6835	Remote Similarity	NPD2652	Approved
0.6824	Remote Similarity	NPD3664	Approved
0.6824	Remote Similarity	NPD3661	Approved
0.6824	Remote Similarity	NPD3663	Approved
0.6824	Remote Similarity	NPD3662	Phase 3
0.6818	Remote Similarity	NPD4172	Approved
0.6818	Remote Similarity	NPD4173	Approved
0.6815	Remote Similarity	NPD7130	Phase 3
0.6809	Remote Similarity	NPD5292	Approved
0.6809	Remote Similarity	NPD5291	Approved
0.68	Remote Similarity	NPD3632	Clinical (unspecified phase)
0.68	Remote Similarity	NPD4619	Approved
0.68	Remote Similarity	NPD4621	Approved
0.6792	Remote Similarity	NPD8389	Clinical (unspecified phase)
0.6786	Remote Similarity	NPD7608	Discontinued
0.6783	Remote Similarity	NPD5981	Approved
0.6779	Remote Similarity	NPD5203	Approved
0.6779	Remote Similarity	NPD4620	Approved
0.6779	Remote Similarity	NPD5263	Approved
0.6779	Remote Similarity	NPD5201	Approved
0.6779	Remote Similarity	NPD4617	Approved
0.6779	Remote Similarity	NPD4676	Approved
0.6774	Remote Similarity	NPD7720	Phase 2
0.677	Remote Similarity	NPD8315	Phase 1
0.6768	Remote Similarity	NPD7599	Phase 2
0.6765	Remote Similarity	NPD5979	Clinical (unspecified phase)
0.6757	Remote Similarity	NPD3588	Discontinued
0.6753	Remote Similarity	NPD7728	Clinical (unspecified phase)
0.6752	Remote Similarity	NPD5298	Clinical (unspecified phase)
0.6736	Remote Similarity	NPD7342	Discontinued
0.6736	Remote Similarity	NPD4488	Clinical (unspecified phase)
0.6735	Remote Similarity	NPD3125	Approved
0.673	Remote Similarity	NPD7892	Clinical (unspecified phase)
0.6727	Remote Similarity	NPD7600	Phase 2
0.6711	Remote Similarity	NPD5204	Approved
0.6711	Remote Similarity	NPD5121	Approved
0.6711	Remote Similarity	NPD3040	Approved
0.6711	Remote Similarity	NPD5120	Approved
0.6711	Remote Similarity	NPD5119	Approved
0.6709	Remote Similarity	NPD6552	Clinical (unspecified phase)
0.6708	Remote Similarity	NPD7131	Phase 3
0.669	Remote Similarity	NPD4106	Approved
0.669	Remote Similarity	NPD4135	Approved
0.669	Remote Similarity	NPD4136	Approved
0.6689	Remote Similarity	NPD5581	Approved
0.6688	Remote Similarity	NPD5264	Approved
0.6688	Remote Similarity	NPD5265	Approved
0.6686	Remote Similarity	NPD5681	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD4646	Approved
0.6667	Remote Similarity	NPD4647	Approved
0.6667	Remote Similarity	NPD4648	Approved
0.6667	Remote Similarity	NPD7978	Discontinued
0.6667	Remote Similarity	NPD7972	Discontinued
0.6667	Remote Similarity	NPD2022	Approved
0.6646	Remote Similarity	NPD6078	Clinical (unspecified phase)
0.6645	Remote Similarity	NPD3480	Approved
0.6643	Remote Similarity	NPD7522	Discontinued
0.6627	Remote Similarity	NPD7080	Clinical (unspecified phase)
0.6623	Remote Similarity	NPD2051	Approved
0.6623	Remote Similarity	NPD2045	Approved
0.6623	Remote Similarity	NPD2047	Approved
0.6623	Remote Similarity	NPD2044	Approved
0.6623	Remote Similarity	NPD2048	Approved
0.6623	Remote Similarity	NPD2046	Approved
0.6623	Remote Similarity	NPD2043	Approved
0.6623	Remote Similarity	NPD2049	Clinical (unspecified phase)
0.6623	Remote Similarity	NPD2050	Clinical (unspecified phase)
0.6623	Remote Similarity	NPD21	Approved
0.6622	Remote Similarity	NPD2634	Clinical (unspecified phase)
0.6608	Remote Similarity	NPD8126	Clinical (unspecified phase)
0.6608	Remote Similarity	NPD8124	Phase 3
0.6603	Remote Similarity	NPD7511	Approved
0.6603	Remote Similarity	NPD7512	Approved
0.6601	Remote Similarity	NPD5323	Approved
0.66	Remote Similarity	NPD7828	Discontinued
0.6599	Remote Similarity	NPD5108	Clinical (unspecified phase)
0.6597	Remote Similarity	NPD6343	Approved
0.6597	Remote Similarity	NPD6345	Approved
0.6579	Remote Similarity	NPD2078	Clinical (unspecified phase)
0.6573	Remote Similarity	NPD4574	Approved
0.6573	Remote Similarity	NPD3123	Discovery
0.6573	Remote Similarity	NPD4576	Approved
0.6568	Remote Similarity	NPD4508	Discontinued
0.6561	Remote Similarity	NPD2087	Approved
0.6561	Remote Similarity	NPD2088	Approved
0.6558	Remote Similarity	NPD3908	Approved
0.6552	Remote Similarity	NPD4102	Approved
0.6552	Remote Similarity	NPD4105	Approved

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