NPASS Compound

Structure

NPC473806 OpenBabel07101719192D 51 58 0 0 1 0 0 0 0 0999 V2000 -6.7880 2.4576 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.4907 2.4576 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5609 0.9074 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.8491 -4.2484 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -10.7471 -3.8485 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -11.0279 -1.1775 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -10.2326 -0.5997 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3403 -0.3038 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3348 -2.1849 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0891 -0.8803 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.6394 0.9831 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6376 -3.2529 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.7880 0.4915 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7863 -2.7614 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6376 -0.3038 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7863 0.1877 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4239 -3.0652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.7880 -2.4576 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.9741 -3.1679 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -1.5906 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.6394 1.9661 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0524 0.0560 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.4890 -2.7614 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -6.7880 -0.4915 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.6394 -1.9661 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.9367 -1.9661 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0017 -2.2699 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.5743 -2.2699 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5778 -0.7953 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.7863 -1.7784 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -7.6394 -0.9831 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.1521 -1.4746 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.9367 -0.9831 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5609 -0.7953 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -8.5743 -0.6793 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.4239 -1.4746 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0354 0.0560 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.9518 -3.2707 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -10.1298 -1.5773 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6376 -1.2868 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.9349 -1.2868 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.4890 -1.7784 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.9349 -0.3038 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.0017 -0.6793 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 2.0524 -1.6467 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.8781 0.2557 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.5270 0.9074 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.5270 -0.7953 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.3348 0.5943 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 -10.5296 -2.4754 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 21 1 0 0 0 0 2 21 1 0 0 0 0 4 38 1 0 0 0 0 5 38 1 0 0 0 0 6 39 1 0 0 0 0 7 39 1 0 0 0 0 8 40 1 0 0 0 0 9 41 1 0 0 0 0 11 13 1 0 0 0 0 11 21 2 0 0 0 0 12 14 1 0 0 0 0 12 23 1 0 0 0 0 13 24 1 0 0 0 0 14 30 1 0 0 0 0 15 16 1 0 0 0 0 15 40 1 0 0 0 0 16 43 1 0 0 0 0 17 23 1 0 0 0 0 17 27 1 0 0 0 0 18 25 2 0 0 0 0 18 26 1 0 0 0 0 19 28 2 0 0 0 0 19 38 1 0 0 0 0 20 29 1 0 0 0 0 20 41 1 0 0 0 0 22 3 1 6 0 0 0 22 34 1 0 0 0 0 22 37 1 0 0 0 0 23 42 1 1 0 0 0 24 31 2 0 0 0 0 24 33 1 0 0 0 0 25 28 1 0 0 0 0 25 31 1 0 0 0 0 26 27 1 0 0 0 0 26 33 2 0 0 0 0 27 36 2 0 0 0 0 29 34 1 6 0 0 0 29 50 1 0 0 0 0 30 40 1 6 0 0 0 30 41 1 0 0 0 0 31 35 1 0 0 0 0 32 28 1 1 0 0 0 32 35 1 0 0 0 0 32 39 1 0 0 0 0 33 44 1 0 0 0 0 34 45 1 1 0 0 0 35 46 1 6 0 0 0 36 42 1 0 0 0 0 36 44 1 0 0 0 0 37 47 2 0 0 0 0 37 48 1 0 0 0 0 38 51 1 0 0 0 0 39 51 1 0 0 0 0 40 42 1 1 0 0 0 41 43 1 6 0 0 0 42 10 1 1 0 0 0 43 49 1 1 0 0 0 43 50 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	701.43
Volume:	737.905
LogP:	7.02
LogD:	3.904
LogS:	-3.665
# Rotatable Bonds:	5
TPSA:	132.24
# H-Bond Aceptor:	8
# H-Bond Donor:	5
# Rings:	8
# Heavy Atoms:	8

MedChem Properties

QED Drug-Likeness Score:	0.202
Synthetic Accessibility Score:	6.07
Fsp3:	0.698
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:	-5.367
MDCK Permeability:	1.1571121831366327e-05
Pgp-inhibitor:	0.855
Pgp-substrate:	0.994
Human Intestinal Absorption (HIA):	0.074
20% Bioavailability (F20%):	0.081
30% Bioavailability (F30%):	0.35

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.657
Plasma Protein Binding (PPB):	94.63982391357422%
Volume Distribution (VD):	1.698
Pgp-substrate:	6.609545707702637%

ADMET: Metabolism

CYP1A2-inhibitor:	0.017
CYP1A2-substrate:	0.942
CYP2C19-inhibitor:	0.034
CYP2C19-substrate:	0.715
CYP2C9-inhibitor:	0.203
CYP2C9-substrate:	0.16
CYP2D6-inhibitor:	0.014
CYP2D6-substrate:	0.081
CYP3A4-inhibitor:	0.482
CYP3A4-substrate:	0.738

ADMET: Excretion

Clearance (CL):	6.037
Half-life (T1/2):	0.03

ADMET: Toxicity

hERG Blockers:	0.272
Human Hepatotoxicity (H-HT):	0.795
Drug-inuced Liver Injury (DILI):	0.821
AMES Toxicity:	0.006
Rat Oral Acute Toxicity:	0.987
Maximum Recommended Daily Dose:	0.986
Skin Sensitization:	0.235
Carcinogencity:	0.91
Eye Corrosion:	0.003
Eye Irritation:	0.006
Respiratory Toxicity:	0.987

Download Data

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

Natural Product: NPC473806

Natural Product ID:	NPC473806
*Common Name:**	Nodulisporic Acid C2
IUPAC Name:	n.a.
Synonyms:	Nodulisporic Acid C2
Standard InCHIKey:	RJBBYXNTYMCJHA-CSPUUSRHSA-N
Standard InCHI:	InChI=1S/C43H59NO7/c1-21(2)11-13-24-31-25(28-19-38(4,5)51-39(6,7)32(28)35(31)46)18-26-27-17-23-12-14-30-40(8,42(23,10)36(27)44-33(24)26)15-16-43(49)41(30,9)20-29(50-43)34(45)22(3)37(47)48/h11,18-19,22-23,29-30,32,34-35,44-46,49H,12-17,20H2,1-10H3,(H,47,48)/t22-,23-,29-,30+,32+,34+,35+,40-,41-,42+,43-/m0/s1
SMILES:	CC(=CCc1c2c(cc3c1[nH]c1c3C[C@H]3[C@@]1(C)[C@@]1(C)CC[C@]4([C@@]([C@@H]1CC3)(C)C[C@H](O4)[C@@H]([C@@H](C(=O)O)C)O)O)C1=CC(OC([C@H]1[C@@H]2O)(C)C)(C)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL452371
PubChem CID:	44584355
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0001634] Naphthofurans

*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
NPO32628	nodulisporium	Genus	Xylariaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15387649]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	NP ID	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
IC50	1
Others	1

Activity Type	# Activity
Organism	1
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT2523	Organism	Ctenocephalides felis	Ctenocephalides felis	LD90	>	142.5	uM	PMID[456210]
NPT2	Others	Unspecified		IC50	=	71.5	nM	PMID[456210]

☑ 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 NPC473806 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	1508
0.2-0.3	3349
0.3-0.4	11785
0.4-0.5	19850
0.5-0.6	4675
0.6-0.7	1032
0.7-0.8	88
0.8-0.85	25
0.85-0.9	10
0.9-0.95	5
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC471634
0.9469	High Similarity	NPC79107
0.9469	High Similarity	NPC475424
0.9272	High Similarity	NPC475476
0.9272	High Similarity	NPC242446
0.912	High Similarity	NPC473565
0.8986	High Similarity	NPC473650
0.8986	High Similarity	NPC160527
0.8824	High Similarity	NPC470843
0.8824	High Similarity	NPC94541
0.8714	High Similarity	NPC97388
0.867	High Similarity	NPC282033
0.8667	High Similarity	NPC473547
0.864	High Similarity	NPC131273
0.864	High Similarity	NPC473441
0.8599	High Similarity	NPC187456
0.8512	High Similarity	NPC61813
0.8483	Intermediate Similarity	NPC250129
0.8447	Intermediate Similarity	NPC183426
0.8436	Intermediate Similarity	NPC475165
0.8349	Intermediate Similarity	NPC469312
0.8349	Intermediate Similarity	NPC41318
0.8333	Intermediate Similarity	NPC311451
0.8302	Intermediate Similarity	NPC284102
0.8287	Intermediate Similarity	NPC96131
0.8274	Intermediate Similarity	NPC278540
0.8238	Intermediate Similarity	NPC471782
0.8238	Intermediate Similarity	NPC471583
0.8194	Intermediate Similarity	NPC471284
0.816	Intermediate Similarity	NPC18661
0.8102	Intermediate Similarity	NPC235900
0.8095	Intermediate Similarity	NPC475151
0.8	Intermediate Similarity	NPC473747
0.7946	Intermediate Similarity	NPC245756
0.7857	Intermediate Similarity	NPC181502
0.7857	Intermediate Similarity	NPC85066
0.785	Intermediate Similarity	NPC123019
0.7848	Intermediate Similarity	NPC470874
0.7788	Intermediate Similarity	NPC34271
0.7719	Intermediate Similarity	NPC470873
0.7656	Intermediate Similarity	NPC119700
0.7653	Intermediate Similarity	NPC231342
0.7583	Intermediate Similarity	NPC206967
0.7565	Intermediate Similarity	NPC249342
0.7546	Intermediate Similarity	NPC32200
0.7512	Intermediate Similarity	NPC165201
0.7452	Intermediate Similarity	NPC198339
0.7441	Intermediate Similarity	NPC99428
0.7416	Intermediate Similarity	NPC302191
0.7407	Intermediate Similarity	NPC205403
0.7404	Intermediate Similarity	NPC6093
0.7333	Intermediate Similarity	NPC204303
0.7289	Intermediate Similarity	NPC234999
0.728	Intermediate Similarity	NPC188239
0.7253	Intermediate Similarity	NPC235885
0.7252	Intermediate Similarity	NPC477135
0.7232	Intermediate Similarity	NPC474905
0.7225	Intermediate Similarity	NPC475778
0.7212	Intermediate Similarity	NPC97525
0.7209	Intermediate Similarity	NPC46413
0.72	Intermediate Similarity	NPC470280
0.713	Intermediate Similarity	NPC204491
0.7106	Intermediate Similarity	NPC141428
0.7098	Intermediate Similarity	NPC476115
0.7076	Intermediate Similarity	NPC472762
0.7073	Intermediate Similarity	NPC473389
0.7073	Intermediate Similarity	NPC107836
0.7051	Intermediate Similarity	NPC2395
0.7046	Intermediate Similarity	NPC57690
0.7033	Intermediate Similarity	NPC199259
0.7026	Intermediate Similarity	NPC249428
0.7008	Intermediate Similarity	NPC37473
0.6991	Remote Similarity	NPC476319
0.6983	Remote Similarity	NPC203614
0.6977	Remote Similarity	NPC472444
0.6974	Remote Similarity	NPC61637
0.6973	Remote Similarity	NPC237901
0.6973	Remote Similarity	NPC195788
0.6964	Remote Similarity	NPC214428
0.6953	Remote Similarity	NPC162812
0.6953	Remote Similarity	NPC314552
0.6944	Remote Similarity	NPC472589
0.6942	Remote Similarity	NPC94428
0.6942	Remote Similarity	NPC263937
0.6939	Remote Similarity	NPC475844
0.6933	Remote Similarity	NPC112547
0.6932	Remote Similarity	NPC472588
0.6926	Remote Similarity	NPC151976
0.6923	Remote Similarity	NPC82070
0.692	Remote Similarity	NPC147446
0.6919	Remote Similarity	NPC126492
0.6916	Remote Similarity	NPC270009
0.6905	Remote Similarity	NPC478080
0.6905	Remote Similarity	NPC154293
0.69	Remote Similarity	NPC127677
0.6889	Remote Similarity	NPC49196
0.6889	Remote Similarity	NPC249150
0.6889	Remote Similarity	NPC79129
0.6889	Remote Similarity	NPC195461
0.6889	Remote Similarity	NPC313985
0.6889	Remote Similarity	NPC81654
0.6888	Remote Similarity	NPC290529
0.6886	Remote Similarity	NPC277350
0.688	Remote Similarity	NPC476516
0.6875	Remote Similarity	NPC471977
0.6875	Remote Similarity	NPC102008
0.6875	Remote Similarity	NPC475644
0.6875	Remote Similarity	NPC471190
0.6875	Remote Similarity	NPC470486
0.687	Remote Similarity	NPC469743
0.6868	Remote Similarity	NPC260909
0.6862	Remote Similarity	NPC267926
0.6856	Remote Similarity	NPC46225
0.6855	Remote Similarity	NPC476517
0.6849	Remote Similarity	NPC266192
0.6849	Remote Similarity	NPC475271
0.6844	Remote Similarity	NPC57453
0.6838	Remote Similarity	NPC30570
0.6838	Remote Similarity	NPC476114
0.6837	Remote Similarity	NPC472443
0.6833	Remote Similarity	NPC87152
0.6833	Remote Similarity	NPC476110
0.6833	Remote Similarity	NPC475631
0.6833	Remote Similarity	NPC475600
0.6828	Remote Similarity	NPC475223
0.6825	Remote Similarity	NPC189079
0.6824	Remote Similarity	NPC229348
0.6822	Remote Similarity	NPC52254
0.6818	Remote Similarity	NPC474701
0.6809	Remote Similarity	NPC1203
0.6803	Remote Similarity	NPC475619
0.68	Remote Similarity	NPC50503
0.6798	Remote Similarity	NPC246983
0.6798	Remote Similarity	NPC475448
0.6797	Remote Similarity	NPC477548
0.6797	Remote Similarity	NPC89549
0.6792	Remote Similarity	NPC473506
0.679	Remote Similarity	NPC30456
0.6787	Remote Similarity	NPC476090
0.6781	Remote Similarity	NPC87856
0.6781	Remote Similarity	NPC292517
0.6778	Remote Similarity	NPC51388
0.6776	Remote Similarity	NPC472586
0.6766	Remote Similarity	NPC132211
0.6765	Remote Similarity	NPC280799
0.6763	Remote Similarity	NPC228377
0.6763	Remote Similarity	NPC122968
0.6763	Remote Similarity	NPC211920
0.6763	Remote Similarity	NPC328186
0.6763	Remote Similarity	NPC477787
0.6762	Remote Similarity	NPC237702
0.6761	Remote Similarity	NPC253482
0.6754	Remote Similarity	NPC474116
0.6754	Remote Similarity	NPC162730
0.6753	Remote Similarity	NPC258062
0.6752	Remote Similarity	NPC267965
0.675	Remote Similarity	NPC475498
0.675	Remote Similarity	NPC475137
0.675	Remote Similarity	NPC477902
0.6749	Remote Similarity	NPC475596
0.6749	Remote Similarity	NPC473689
0.6749	Remote Similarity	NPC477531
0.6749	Remote Similarity	NPC475303
0.6749	Remote Similarity	NPC292416
0.6736	Remote Similarity	NPC252251
0.6736	Remote Similarity	NPC274640
0.6735	Remote Similarity	NPC277351
0.6729	Remote Similarity	NPC34508
0.6726	Remote Similarity	NPC55493
0.6725	Remote Similarity	NPC98715
0.6722	Remote Similarity	NPC202503
0.6721	Remote Similarity	NPC320324
0.6721	Remote Similarity	NPC319880
0.6721	Remote Similarity	NPC244839
0.6719	Remote Similarity	NPC133609
0.671	Remote Similarity	NPC225821
0.6708	Remote Similarity	NPC209174
0.6708	Remote Similarity	NPC76565
0.6696	Remote Similarity	NPC241024
0.6694	Remote Similarity	NPC124029
0.6681	Remote Similarity	NPC137589
0.6681	Remote Similarity	NPC84815
0.6681	Remote Similarity	NPC301368
0.6681	Remote Similarity	NPC31700
0.668	Remote Similarity	NPC475648
0.668	Remote Similarity	NPC316841
0.668	Remote Similarity	NPC473850
0.668	Remote Similarity	NPC6786
0.668	Remote Similarity	NPC150698
0.668	Remote Similarity	NPC96801
0.6667	Remote Similarity	NPC476106
0.6667	Remote Similarity	NPC327769
0.6667	Remote Similarity	NPC475362
0.6667	Remote Similarity	NPC170751
0.6667	Remote Similarity	NPC9894
0.6667	Remote Similarity	NPC475426
0.6667	Remote Similarity	NPC475406
0.6667	Remote Similarity	NPC35208
0.6654	Remote Similarity	NPC473800
0.6653	Remote Similarity	NPC474192

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 NPC473806 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	255
0.1-0.2	549
0.2-0.3	747
0.3-0.4	2267
0.4-0.5	3672
0.5-0.6	1449
0.6-0.7	194
0.7-0.8	17
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
0.7409	Intermediate Similarity	NPD2920	Discontinued
0.7336	Intermediate Similarity	NPD2565	Phase 2
0.7336	Intermediate Similarity	NPD2564	Approved
0.7215	Intermediate Similarity	NPD5003	Discontinued
0.7021	Intermediate Similarity	NPD6995	Phase 1
0.6973	Remote Similarity	NPD8466	Approved
0.6973	Remote Similarity	NPD8465	Approved
0.6973	Remote Similarity	NPD8428	Approved
0.6973	Remote Similarity	NPD8427	Approved
0.6973	Remote Similarity	NPD8429	Approved
0.6973	Remote Similarity	NPD8467	Approved
0.6958	Remote Similarity	NPD7688	Phase 1
0.6953	Remote Similarity	NPD5164	Discontinued
0.6938	Remote Similarity	NPD8363	Approved
0.6938	Remote Similarity	NPD8364	Approved
0.6909	Remote Similarity	NPD6630	Clinical (unspecified phase)
0.6889	Remote Similarity	NPD4601	Approved
0.6889	Remote Similarity	NPD4600	Approved
0.6885	Remote Similarity	NPD8365	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD53	Approved
0.6875	Remote Similarity	NPD7777	Approved
0.6875	Remote Similarity	NPD7778	Approved
0.6868	Remote Similarity	NPD8460	Approved
0.6868	Remote Similarity	NPD8425	Approved
0.6868	Remote Similarity	NPD8459	Approved
0.6868	Remote Similarity	NPD8426	Approved
0.6795	Remote Similarity	NPD7707	Approved
0.6783	Remote Similarity	NPD6456	Discontinued
0.6753	Remote Similarity	NPD8423	Phase 2
0.6753	Remote Similarity	NPD8399	Phase 1
0.6746	Remote Similarity	NPD7769	Phase 3
0.6726	Remote Similarity	NPD7946	Pre-registration
0.6707	Remote Similarity	NPD7770	Phase 3
0.6681	Remote Similarity	NPD6455	Phase 3
0.6667	Remote Similarity	NPD7957	Phase 1
0.6667	Remote Similarity	NPD7958	Clinical (unspecified phase)
0.6653	Remote Similarity	NPD6717	Clinical (unspecified phase)
0.6638	Remote Similarity	NPD5429	Discontinued
0.6636	Remote Similarity	NPD6641	Approved
0.6636	Remote Similarity	NPD6642	Approved
0.6628	Remote Similarity	NPD7955	Approved
0.6628	Remote Similarity	NPD7956	Approved
0.6625	Remote Similarity	NPD5507	Approved
0.6625	Remote Similarity	NPD5506	Approved
0.661	Remote Similarity	NPD7571	Clinical (unspecified phase)
0.6609	Remote Similarity	NPD5721	Clinical (unspecified phase)
0.6602	Remote Similarity	NPD7708	Approved
0.6594	Remote Similarity	NPD8489	Phase 1
0.6588	Remote Similarity	NPD6503	Clinical (unspecified phase)
0.6581	Remote Similarity	NPD5835	Phase 3
0.6581	Remote Similarity	NPD5834	Phase 3
0.6569	Remote Similarity	NPD7878	Phase 2
0.6561	Remote Similarity	NPD8468	Phase 2
0.6557	Remote Similarity	NPD6977	Clinical (unspecified phase)
0.6557	Remote Similarity	NPD6978	Phase 2
0.6555	Remote Similarity	NPD8160	Phase 2
0.6543	Remote Similarity	NPD3925	Approved
0.6538	Remote Similarity	NPD7947	Clinical (unspecified phase)
0.6528	Remote Similarity	NPD6739	Clinical (unspecified phase)
0.6527	Remote Similarity	NPD8327	Clinical (unspecified phase)
0.6527	Remote Similarity	NPD8325	Phase 3
0.6527	Remote Similarity	NPD8326	Phase 3
0.6525	Remote Similarity	NPD7470	Discontinued
0.6524	Remote Similarity	NPD4901	Clinical (unspecified phase)
0.6518	Remote Similarity	NPD7234	Approved
0.6518	Remote Similarity	NPD7233	Approved
0.6513	Remote Similarity	NPD8112	Clinical (unspecified phase)
0.6502	Remote Similarity	NPD7803	Approved
0.65	Remote Similarity	NPD5899	Approved
0.65	Remote Similarity	NPD5898	Approved
0.65	Remote Similarity	NPD5897	Approved
0.6498	Remote Similarity	NPD43	Approved
0.6498	Remote Similarity	NPD6182	Approved
0.6498	Remote Similarity	NPD6183	Clinical (unspecified phase)
0.6485	Remote Similarity	NPD7496	Phase 2
0.6481	Remote Similarity	NPD8283	Approved
0.6481	Remote Similarity	NPD6138	Clinical (unspecified phase)
0.6481	Remote Similarity	NPD56	Approved
0.6481	Remote Similarity	NPD8282	Approved
0.6475	Remote Similarity	NPD6976	Clinical (unspecified phase)
0.6471	Remote Similarity	NPD8358	Approved
0.6471	Remote Similarity	NPD8094	Discontinued
0.6457	Remote Similarity	NPD7921	Approved
0.6453	Remote Similarity	NPD4862	Clinical (unspecified phase)
0.6452	Remote Similarity	NPD3746	Discontinued
0.6444	Remote Similarity	NPD4897	Phase 2
0.6435	Remote Similarity	NPD2844	Phase 3
0.6429	Remote Similarity	NPD8093	Discontinued
0.6421	Remote Similarity	NPD7181	Phase 3
0.6416	Remote Similarity	NPD6281	Approved
0.641	Remote Similarity	NPD5901	Discontinued
0.6407	Remote Similarity	NPD6661	Clinical (unspecified phase)
0.6407	Remote Similarity	NPD6249	Phase 2
0.6407	Remote Similarity	NPD6248	Phase 2
0.6406	Remote Similarity	NPD7474	Suspended
0.6398	Remote Similarity	NPD7772	Phase 3
0.6393	Remote Similarity	NPD6160	Clinical (unspecified phase)
0.6388	Remote Similarity	NPD5913	Phase 3
0.6388	Remote Similarity	NPD5912	Clinical (unspecified phase)
0.6387	Remote Similarity	NPD5936	Approved
0.6387	Remote Similarity	NPD5939	Approved
0.638	Remote Similarity	NPD5398	Clinical (unspecified phase)
0.6375	Remote Similarity	NPD7073	Clinical (unspecified phase)
0.6371	Remote Similarity	NPD7941	Phase 3
0.6364	Remote Similarity	NPD8016	Phase 3
0.6364	Remote Similarity	NPD7395	Discontinued
0.6364	Remote Similarity	NPD8017	Clinical (unspecified phase)
0.636	Remote Similarity	NPD7069	Discontinued
0.6353	Remote Similarity	NPD6773	Clinical (unspecified phase)
0.6348	Remote Similarity	NPD5512	Phase 3
0.6347	Remote Similarity	NPD7418	Discontinued
0.6344	Remote Similarity	NPD4499	Approved
0.6333	Remote Similarity	NPD3795	Approved
0.6333	Remote Similarity	NPD3794	Approved
0.633	Remote Similarity	NPD1326	Approved
0.633	Remote Similarity	NPD1325	Approved
0.6329	Remote Similarity	NPD2509	Approved
0.6329	Remote Similarity	NPD2510	Approved
0.6318	Remote Similarity	NPD7927	Clinical (unspecified phase)
0.6316	Remote Similarity	NPD3785	Clinical (unspecified phase)
0.6314	Remote Similarity	NPD6517	Phase 3
0.6314	Remote Similarity	NPD7010	Phase 3
0.6313	Remote Similarity	NPD4554	Clinical (unspecified phase)
0.6309	Remote Similarity	NPD4501	Approved
0.6309	Remote Similarity	NPD4500	Approved
0.6305	Remote Similarity	NPD7824	Approved
0.6305	Remote Similarity	NPD7589	Clinical (unspecified phase)
0.6303	Remote Similarity	NPD4506	Discontinued
0.63	Remote Similarity	NPD4334	Discontinued
0.6298	Remote Similarity	NPD6176	Phase 1
0.6295	Remote Similarity	NPD7950	Approved
0.6295	Remote Similarity	NPD7951	Approved
0.6295	Remote Similarity	NPD7953	Approved
0.6295	Remote Similarity	NPD7790	Approved
0.6295	Remote Similarity	NPD7952	Approved
0.6295	Remote Similarity	NPD7789	Approved
0.6295	Remote Similarity	NPD7791	Approved
0.629	Remote Similarity	NPD7268	Clinical (unspecified phase)
0.6287	Remote Similarity	NPD6838	Clinical (unspecified phase)
0.6282	Remote Similarity	NPD4511	Phase 1
0.628	Remote Similarity	NPD8372	Clinical (unspecified phase)
0.6276	Remote Similarity	NPD4900	Clinical (unspecified phase)
0.6275	Remote Similarity	NPD7417	Discontinued
0.6266	Remote Similarity	NPD3800	Clinical (unspecified phase)
0.6265	Remote Similarity	NPD7780	Approved
0.6265	Remote Similarity	NPD7781	Approved
0.6261	Remote Similarity	NPD6376	Discontinued
0.6256	Remote Similarity	NPD4948	Discontinued
0.625	Remote Similarity	NPD6206	Phase 1
0.624	Remote Similarity	NPD5488	Discontinued
0.6239	Remote Similarity	NPD6479	Discontinued
0.6234	Remote Similarity	NPD2125	Clinical (unspecified phase)
0.623	Remote Similarity	NPD8109	Clinical (unspecified phase)
0.6229	Remote Similarity	NPD5487	Phase 1
0.6228	Remote Similarity	NPD1534	Approved
0.6225	Remote Similarity	NPD7731	Approved
0.6225	Remote Similarity	NPD6292	Clinical (unspecified phase)
0.6225	Remote Similarity	NPD7730	Approved
0.6223	Remote Similarity	NPD6261	Phase 3
0.6222	Remote Similarity	NPD8658	Clinical (unspecified phase)
0.6217	Remote Similarity	NPD4315	Phase 2
0.6214	Remote Similarity	NPD3394	Approved
0.6214	Remote Similarity	NPD7218	Clinical (unspecified phase)
0.6214	Remote Similarity	NPD3393	Approved
0.6214	Remote Similarity	NPD3389	Approved
0.6213	Remote Similarity	NPD7931	Approved
0.6213	Remote Similarity	NPD7933	Approved
0.6213	Remote Similarity	NPD7932	Clinical (unspecified phase)
0.6213	Remote Similarity	NPD7934	Discovery
0.6193	Remote Similarity	NPD5744	Clinical (unspecified phase)
0.6192	Remote Similarity	NPD2916	Discontinued
0.619	Remote Similarity	NPD4885	Approved
0.619	Remote Similarity	NPD7797	Approved
0.619	Remote Similarity	NPD7796	Approved
0.618	Remote Similarity	NPD7238	Clinical (unspecified phase)
0.6176	Remote Similarity	NPD6732	Clinical (unspecified phase)
0.6169	Remote Similarity	NPD7717	Approved
0.6169	Remote Similarity	NPD7716	Approved
0.6168	Remote Similarity	NPD5257	Clinical (unspecified phase)
0.616	Remote Similarity	NPD8072	Approved
0.6157	Remote Similarity	NPD6657	Clinical (unspecified phase)
0.615	Remote Similarity	NPD5728	Clinical (unspecified phase)
0.615	Remote Similarity	NPD5596	Phase 2
0.6148	Remote Similarity	NPD7576	Discontinued
0.6145	Remote Similarity	NPD7271	Approved
0.6141	Remote Similarity	NPD7998	Clinical (unspecified phase)
0.6138	Remote Similarity	NPD6770	Approved
0.6138	Remote Similarity	NPD3763	Approved
0.6137	Remote Similarity	NPD6550	Discontinued
0.6135	Remote Similarity	NPD7710	Clinical (unspecified phase)
0.6135	Remote Similarity	NPD7767	Approved
0.6134	Remote Similarity	NPD8098	Approved
0.6128	Remote Similarity	NPD8395	Approved
0.6128	Remote Similarity	NPD8396	Approved
0.6118	Remote Similarity	NPD8073	Approved
0.6118	Remote Similarity	NPD5891	Approved
0.6116	Remote Similarity	NPD7070	Clinical (unspecified phase)
0.6114	Remote Similarity	NPD8431	Approved
0.6109	Remote Similarity	NPD3003	Approved
0.6109	Remote Similarity	NPD6245	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