NPASS Compound

Structure

NPC199259 OpenBabel07101718282D 44 53 0 0 1 0 0 0 0 0999 V2000 9.0401 -3.1198 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.6546 -1.5749 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2795 -0.1182 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9185 1.7760 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9613 1.7039 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0736 -2.5362 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2012 -1.8025 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3026 0.5538 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.6109 -2.6506 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.7189 -2.2958 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1946 0.1990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2764 -0.9213 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6457 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7689 -2.2837 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.9014 -2.1700 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3600 -0.3941 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 0.1879 -1.1846 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5494 -0.0413 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8452 0.6141 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.2137 -1.8740 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4353 -2.1051 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.3641 -2.0555 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.5326 -0.0358 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.7108 -0.7345 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2965 -1.1552 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1570 -0.7297 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.8706 -0.8653 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 8.0094 -1.8152 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.6031 0.1203 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.8276 -1.4167 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9786 -0.5105 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.5024 0.9109 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5801 -1.3459 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.6881 -0.9912 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 5.3334 -0.7508 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 6.2254 -1.1056 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.6350 -2.3226 0.0000 Cl 0 0 0 0 0 0 0 0 0 0 0 0 2.3815 -2.2667 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 8.6239 -0.2702 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.8399 0.4394 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 7.2561 -2.4103 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.1966 0.7159 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.0866 -0.1557 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 15 2 0 0 0 0 2 15 1 0 0 0 0 3 16 2 0 0 0 0 4 33 1 0 0 0 0 5 33 1 0 0 0 0 6 34 1 0 0 0 0 8 11 1 0 0 0 0 8 19 1 0 0 0 0 9 10 1 0 0 0 0 9 23 1 0 0 0 0 10 34 1 0 0 0 0 11 36 1 0 0 0 0 12 16 1 0 0 0 0 12 18 1 0 0 0 0 14 21 2 0 0 0 0 14 22 1 0 0 0 0 16 17 1 0 0 0 0 17 13 1 1 0 0 0 17 24 1 0 0 0 0 18 21 1 0 0 0 0 18 25 2 0 0 0 0 19 30 1 0 0 0 0 19 35 1 6 0 0 0 20 13 1 6 0 0 0 20 24 1 0 0 0 0 20 33 1 0 0 0 0 21 38 1 0 0 0 0 22 26 2 0 0 0 0 22 39 1 0 0 0 0 23 37 1 1 0 0 0 23 42 1 0 0 0 0 24 25 1 1 0 0 0 25 26 1 0 0 0 0 26 27 1 0 0 0 0 27 31 2 0 0 0 0 28 29 1 0 0 0 0 28 32 1 0 0 0 0 28 40 1 1 0 0 0 29 15 1 1 0 0 0 29 42 1 0 0 0 0 30 27 1 1 0 0 0 30 43 1 0 0 0 0 31 35 1 0 0 0 0 31 39 1 0 0 0 0 32 37 1 6 0 0 0 32 44 1 0 0 0 0 33 43 1 0 0 0 0 34 35 1 6 0 0 0 35 7 1 6 0 0 0 36 34 1 6 0 0 0 36 41 1 0 0 0 0 37 36 1 1 0 0 0 37 44 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	617.29
Volume:	617.284
LogP:	7.263
LogD:	4.295
LogS:	-5.124
# Rotatable Bonds:	1
TPSA:	87.24
# H-Bond Aceptor:	6
# H-Bond Donor:	3
# Rings:	10
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.249
Synthetic Accessibility Score:	6.548
Fsp3:	0.676
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:	-5.319
MDCK Permeability:	1.072281247616047e-05
Pgp-inhibitor:	0.946
Pgp-substrate:	0.994
Human Intestinal Absorption (HIA):	0.013
20% Bioavailability (F20%):	0.845
30% Bioavailability (F30%):	0.559

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.915
Plasma Protein Binding (PPB):	93.14514923095703%
Volume Distribution (VD):	2.279
Pgp-substrate:	3.0711960792541504%

ADMET: Metabolism

CYP1A2-inhibitor:	0.041
CYP1A2-substrate:	0.973
CYP2C19-inhibitor:	0.199
CYP2C19-substrate:	0.795
CYP2C9-inhibitor:	0.374
CYP2C9-substrate:	0.062
CYP2D6-inhibitor:	0.079
CYP2D6-substrate:	0.31
CYP3A4-inhibitor:	0.73
CYP3A4-substrate:	0.914

ADMET: Excretion

Clearance (CL):	7.264
Half-life (T1/2):	0.013

ADMET: Toxicity

hERG Blockers:	0.968
Human Hepatotoxicity (H-HT):	0.336
Drug-inuced Liver Injury (DILI):	0.888
AMES Toxicity:	0.017
Rat Oral Acute Toxicity:	0.979
Maximum Recommended Daily Dose:	0.984
Skin Sensitization:	0.462
Carcinogencity:	0.916
Eye Corrosion:	0.003
Eye Irritation:	0.01
Respiratory Toxicity:	0.992

Download Data

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

Natural Product: NPC199259

Natural Product ID:	NPC199259
*Common Name:**	Penitrem F
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	YWORPEZTBDVGCS-JCMMWUKFSA-N
Standard InCHI:	InChI=1S/C37H44ClNO5/c1-15(2)29-28(40)32-37(44-32)23(42-29)9-10-34(6)35(7)19(8-11-36(34,37)41)30-27-26-22(39-31(27)35)14-21(38)18-12-16(3)17-13-20(24(17)25(18)26)33(4,5)43-30/h14,17,19-20,23-24,28-30,32,39-41H,1,3,8-13H2,2,4-7H3/t17-,19+,20+,23+,24+,28+,29-,30+,32-,34-,35-,36+,37+/m1/s1
SMILES:	CC(=C)[C@H]1O[C@H]2CC[C@]3([C@@]([C@]42[C@@H]([C@H]1O)O4)(O)CC[C@@H]1[C@]3(C)c2[nH]c3c4c2[C@H]1OC(C)(C)[C@@H]1[C@H]2c4c(c(c3)Cl)CC(=C)[C@H]2C1)C
Synthetic Gene Cluster:	BGC0001375;
ChEMBL Identifier:	CHEMBL2272678
PubChem CID:	3086086
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]
NPO40568	Mucor irregularis QEN-189	Strain	Mucoraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[27462726]
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	5
Others	6

Activity Type	# Activity
Cell Line	3
NON-MOLECULAR	2
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	IC50	=	35000.0	nM	PMID[456508]
NPT82	Cell Line	MDA-MB-231	Homo sapiens	IC50	=	13800.0	nM	PMID[456508]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	=	15000.0	nM	PMID[456508]
NPT6649	Organism	Ceratitis capitata	Ceratitis capitata	Activity	=	100.0	%	PMID[456507]
NPT6649	Organism	Ceratitis capitata	Ceratitis capitata	Activity	=	0.0	%	PMID[456507]
NPT6649	Organism	Ceratitis capitata	Ceratitis capitata	mortality	=	66.6	%	PMID[456507]
NPT2212	Organism	Oncopeltus fasciatus	Oncopeltus fasciatus	Survival	=	9.5	%	PMID[456507]
NPT2212	Organism	Oncopeltus fasciatus	Oncopeltus fasciatus	mortality	=	20.3	%	PMID[456507]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	8200.0	nM	PMID[456509]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	3300.0	nM	PMID[456509]

☑ 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 NPC199259 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	654
0.1-0.2	2369
0.2-0.3	8334
0.3-0.4	21430
0.4-0.5	7324
0.5-0.6	2062
0.6-0.7	462
0.7-0.8	40
0.8-0.85	10
0.85-0.9	3
0.9-0.95	6
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9954	High Similarity	NPC473389
0.9541	High Similarity	NPC188239
0.9128	High Similarity	NPC249342
0.8784	High Similarity	NPC470873
0.8682	High Similarity	NPC470874
0.7298	Intermediate Similarity	NPC470843
0.7298	Intermediate Similarity	NPC94541
0.7289	Intermediate Similarity	NPC231342
0.7197	Intermediate Similarity	NPC61813
0.7071	Intermediate Similarity	NPC96131
0.7069	Intermediate Similarity	NPC477135
0.7033	Intermediate Similarity	NPC473806
0.7033	Intermediate Similarity	NPC471634
0.7021	Intermediate Similarity	NPC61637
0.6987	Remote Similarity	NPC473650
0.6987	Remote Similarity	NPC160527
0.698	Remote Similarity	NPC79107
0.698	Remote Similarity	NPC475424
0.6978	Remote Similarity	NPC119700
0.6947	Remote Similarity	NPC34271
0.6942	Remote Similarity	NPC475476
0.6942	Remote Similarity	NPC242446
0.6935	Remote Similarity	NPC282033
0.6917	Remote Similarity	NPC471284
0.6904	Remote Similarity	NPC235900
0.6897	Remote Similarity	NPC32200
0.6891	Remote Similarity	NPC475165
0.6862	Remote Similarity	NPC250129
0.6844	Remote Similarity	NPC165201
0.6805	Remote Similarity	NPC473547
0.6795	Remote Similarity	NPC475151
0.6793	Remote Similarity	NPC187456
0.6777	Remote Similarity	NPC97388
0.6767	Remote Similarity	NPC205403
0.6756	Remote Similarity	NPC302191
0.6681	Remote Similarity	NPC476175
0.6653	Remote Similarity	NPC18661
0.6653	Remote Similarity	NPC204303
0.6641	Remote Similarity	NPC473565
0.664	Remote Similarity	NPC112547
0.6638	Remote Similarity	NPC473747
0.6637	Remote Similarity	NPC198339
0.6597	Remote Similarity	NPC123019
0.6586	Remote Similarity	NPC41318
0.6586	Remote Similarity	NPC469312
0.6548	Remote Similarity	NPC183426
0.652	Remote Similarity	NPC6093
0.6518	Remote Similarity	NPC314552
0.6502	Remote Similarity	NPC154293
0.6489	Remote Similarity	NPC97525
0.6454	Remote Similarity	NPC472842
0.6435	Remote Similarity	NPC19679
0.6434	Remote Similarity	NPC284102
0.6421	Remote Similarity	NPC1203
0.6406	Remote Similarity	NPC477531
0.6392	Remote Similarity	NPC252251
0.6379	Remote Similarity	NPC476319
0.6379	Remote Similarity	NPC476106
0.6367	Remote Similarity	NPC209174
0.6364	Remote Similarity	NPC472444
0.6343	Remote Similarity	NPC131273
0.6343	Remote Similarity	NPC473441
0.634	Remote Similarity	NPC206967
0.629	Remote Similarity	NPC48353
0.6289	Remote Similarity	NPC57690
0.6286	Remote Similarity	NPC193777
0.6285	Remote Similarity	NPC477532
0.6281	Remote Similarity	NPC267423
0.6281	Remote Similarity	NPC476044
0.6274	Remote Similarity	NPC37473
0.6269	Remote Similarity	NPC277351
0.6265	Remote Similarity	NPC475602
0.6265	Remote Similarity	NPC478074
0.626	Remote Similarity	NPC278540
0.6255	Remote Similarity	NPC249428
0.625	Remote Similarity	NPC192270
0.6239	Remote Similarity	NPC473189
0.6236	Remote Similarity	NPC471583
0.6236	Remote Similarity	NPC471782
0.6235	Remote Similarity	NPC201697
0.6235	Remote Similarity	NPC473667
0.6234	Remote Similarity	NPC85066
0.6234	Remote Similarity	NPC270009
0.6234	Remote Similarity	NPC181502
0.6234	Remote Similarity	NPC472443
0.6229	Remote Similarity	NPC46413
0.6226	Remote Similarity	NPC476492
0.6217	Remote Similarity	NPC107836
0.6216	Remote Similarity	NPC290529
0.6211	Remote Similarity	NPC475137
0.6211	Remote Similarity	NPC473850
0.6211	Remote Similarity	NPC141428
0.6211	Remote Similarity	NPC475498
0.621	Remote Similarity	NPC234999
0.6203	Remote Similarity	NPC284141
0.6203	Remote Similarity	NPC311451
0.6202	Remote Similarity	NPC475644
0.6202	Remote Similarity	NPC471190
0.6202	Remote Similarity	NPC470486
0.6202	Remote Similarity	NPC475362
0.6202	Remote Similarity	NPC471977
0.6192	Remote Similarity	NPC79293
0.6192	Remote Similarity	NPC30456
0.6192	Remote Similarity	NPC279401
0.6187	Remote Similarity	NPC267926
0.6183	Remote Similarity	NPC153042
0.6174	Remote Similarity	NPC472586
0.6172	Remote Similarity	NPC76565
0.6172	Remote Similarity	NPC266192
0.6172	Remote Similarity	NPC57797
0.6172	Remote Similarity	NPC250807
0.6169	Remote Similarity	NPC70155
0.6169	Remote Similarity	NPC237702
0.6166	Remote Similarity	NPC62367
0.6163	Remote Similarity	NPC228377
0.6163	Remote Similarity	NPC87152
0.6163	Remote Similarity	NPC122968
0.6163	Remote Similarity	NPC146824
0.6163	Remote Similarity	NPC477787
0.6163	Remote Similarity	NPC475631
0.6163	Remote Similarity	NPC475600
0.6163	Remote Similarity	NPC476110
0.6163	Remote Similarity	NPC328186
0.6163	Remote Similarity	NPC110151
0.616	Remote Similarity	NPC177056
0.616	Remote Similarity	NPC472553
0.616	Remote Similarity	NPC246700
0.616	Remote Similarity	NPC475778
0.6154	Remote Similarity	NPC316841
0.6154	Remote Similarity	NPC475303
0.6154	Remote Similarity	NPC473689
0.6154	Remote Similarity	NPC292416
0.6154	Remote Similarity	NPC475596
0.6151	Remote Similarity	NPC477907
0.6151	Remote Similarity	NPC477909
0.6151	Remote Similarity	NPC42678
0.6151	Remote Similarity	NPC204491
0.6148	Remote Similarity	NPC98371
0.6148	Remote Similarity	NPC313884
0.6145	Remote Similarity	NPC475406
0.6142	Remote Similarity	NPC216428
0.6134	Remote Similarity	NPC106833
0.6134	Remote Similarity	NPC469497
0.6134	Remote Similarity	NPC95783
0.6134	Remote Similarity	NPC471564
0.6133	Remote Similarity	NPC106593
0.613	Remote Similarity	NPC319880
0.613	Remote Similarity	NPC244839
0.613	Remote Similarity	NPC320324
0.6124	Remote Similarity	NPC200888
0.6124	Remote Similarity	NPC473506
0.6122	Remote Similarity	NPC475085
0.6122	Remote Similarity	NPC475112
0.6122	Remote Similarity	NPC38959
0.6122	Remote Similarity	NPC327904
0.6122	Remote Similarity	NPC291535
0.6121	Remote Similarity	NPC293472
0.6116	Remote Similarity	NPC243834
0.6116	Remote Similarity	NPC70956
0.6107	Remote Similarity	NPC473182
0.6104	Remote Similarity	NPC472550
0.6104	Remote Similarity	NPC48042
0.6104	Remote Similarity	NPC304179
0.6102	Remote Similarity	NPC469594
0.6102	Remote Similarity	NPC144779
0.6102	Remote Similarity	NPC294579
0.6098	Remote Similarity	NPC162484
0.6095	Remote Similarity	NPC476514
0.6095	Remote Similarity	NPC472843
0.6094	Remote Similarity	NPC477912
0.6092	Remote Similarity	NPC128751
0.6091	Remote Similarity	NPC72211
0.609	Remote Similarity	NPC217554
0.609	Remote Similarity	NPC475844
0.6087	Remote Similarity	NPC30570
0.6087	Remote Similarity	NPC477910
0.6085	Remote Similarity	NPC139291
0.6085	Remote Similarity	NPC235885
0.6085	Remote Similarity	NPC477902
0.6085	Remote Similarity	NPC472108
0.6084	Remote Similarity	NPC327769
0.6084	Remote Similarity	NPC170751
0.608	Remote Similarity	NPC475422
0.6078	Remote Similarity	NPC472555
0.6078	Remote Similarity	NPC223590
0.6076	Remote Similarity	NPC99428
0.6075	Remote Similarity	NPC11408
0.607	Remote Similarity	NPC122463
0.6066	Remote Similarity	NPC476493
0.6064	Remote Similarity	NPC63041
0.6063	Remote Similarity	NPC206343
0.6063	Remote Similarity	NPC477908
0.6063	Remote Similarity	NPC162812
0.6063	Remote Similarity	NPC475408
0.6063	Remote Similarity	NPC471014
0.6063	Remote Similarity	NPC6981
0.6062	Remote Similarity	NPC148860
0.6062	Remote Similarity	NPC202503
0.6061	Remote Similarity	NPC34508
0.6055	Remote Similarity	NPC477533

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 NPC199259 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	353
0.1-0.2	632
0.2-0.3	1051
0.3-0.4	3108
0.4-0.5	3066
0.5-0.6	873
0.6-0.7	67
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
0.6578	Remote Similarity	NPD6503	Clinical (unspecified phase)
0.6518	Remote Similarity	NPD5164	Discontinued
0.635	Remote Similarity	NPD6773	Clinical (unspecified phase)
0.6333	Remote Similarity	NPD7169	Suspended
0.6296	Remote Similarity	NPD8244	Phase 2
0.6292	Remote Similarity	NPD2727	Phase 2
0.6245	Remote Similarity	NPD4305	Clinical (unspecified phase)
0.6226	Remote Similarity	NPD6978	Phase 2
0.6226	Remote Similarity	NPD6977	Clinical (unspecified phase)
0.6196	Remote Similarity	NPD7221	Approved
0.6196	Remote Similarity	NPD7219	Approved
0.6183	Remote Similarity	NPD5003	Discontinued
0.6176	Remote Similarity	NPD5913	Phase 3
0.6176	Remote Similarity	NPD5912	Clinical (unspecified phase)
0.6148	Remote Similarity	NPD7931	Approved
0.6148	Remote Similarity	NPD6976	Clinical (unspecified phase)
0.6148	Remote Similarity	NPD7932	Clinical (unspecified phase)
0.6148	Remote Similarity	NPD7933	Approved
0.6148	Remote Similarity	NPD7934	Discovery
0.6142	Remote Similarity	NPD6455	Phase 3
0.6118	Remote Similarity	NPD6717	Clinical (unspecified phase)
0.6106	Remote Similarity	NPD972	Clinical (unspecified phase)
0.6091	Remote Similarity	NPD3230	Clinical (unspecified phase)
0.6071	Remote Similarity	NPD8364	Approved
0.6071	Remote Similarity	NPD8363	Approved
0.6056	Remote Similarity	NPD5936	Approved
0.6056	Remote Similarity	NPD8427	Approved
0.6056	Remote Similarity	NPD5939	Approved
0.6056	Remote Similarity	NPD8429	Approved
0.6056	Remote Similarity	NPD8428	Approved
0.6055	Remote Similarity	NPD3280	Approved
0.604	Remote Similarity	NPD2125	Clinical (unspecified phase)
0.6033	Remote Similarity	NPD3791	Clinical (unspecified phase)
0.6032	Remote Similarity	NPD2920	Discontinued
0.603	Remote Similarity	NPD7576	Discontinued
0.6028	Remote Similarity	NPD8426	Approved
0.6028	Remote Similarity	NPD8365	Clinical (unspecified phase)
0.6028	Remote Similarity	NPD8425	Approved
0.6024	Remote Similarity	NPD7218	Clinical (unspecified phase)
0.6008	Remote Similarity	NPD6736	Discontinued
0.6008	Remote Similarity	NPD1322	Clinical (unspecified phase)
0.6008	Remote Similarity	NPD6995	Phase 1
0.6	Remote Similarity	NPD8465	Approved
0.6	Remote Similarity	NPD8467	Approved
0.6	Remote Similarity	NPD2565	Phase 2
0.6	Remote Similarity	NPD2564	Approved
0.6	Remote Similarity	NPD8466	Approved
0.5991	Remote Similarity	NPD4112	Clinical (unspecified phase)
0.5985	Remote Similarity	NPD7558	Phase 2
0.5985	Remote Similarity	NPD6494	Phase 2
0.5985	Remote Similarity	NPD7548	Discontinued
0.5984	Remote Similarity	NPD3003	Approved
0.5984	Remote Similarity	NPD5902	Approved
0.5984	Remote Similarity	NPD7073	Clinical (unspecified phase)
0.5984	Remote Similarity	NPD5903	Approved
0.5978	Remote Similarity	NPD7772	Phase 3
0.5974	Remote Similarity	NPD1325	Approved
0.5974	Remote Similarity	NPD1326	Approved
0.5974	Remote Similarity	NPD7474	Suspended
0.5963	Remote Similarity	NPD4350	Approved
0.5963	Remote Similarity	NPD4349	Approved
0.5961	Remote Similarity	NPD6803	Clinical (unspecified phase)
0.5958	Remote Similarity	NPD1534	Approved
0.5957	Remote Similarity	NPD7956	Approved
0.5957	Remote Similarity	NPD7955	Approved
0.5957	Remote Similarity	NPD1503	Clinical (unspecified phase)
0.5949	Remote Similarity	NPD5596	Phase 2
0.5948	Remote Similarity	NPD4876	Phase 3
0.5948	Remote Similarity	NPD4875	Phase 3
0.5947	Remote Similarity	NPD1554	Clinical (unspecified phase)
0.5929	Remote Similarity	NPD4502	Phase 2
0.5923	Remote Similarity	NPD7418	Discontinued
0.5917	Remote Similarity	NPD8460	Approved
0.5917	Remote Similarity	NPD8459	Approved
0.5914	Remote Similarity	NPD8109	Clinical (unspecified phase)
0.5909	Remote Similarity	NPD4699	Discontinued
0.5894	Remote Similarity	NPD7889	Clinical (unspecified phase)
0.5882	Remote Similarity	NPD8468	Phase 2
0.5878	Remote Similarity	NPD7708	Approved
0.5863	Remote Similarity	NPD5669	Clinical (unspecified phase)
0.5857	Remote Similarity	NPD2715	Clinical (unspecified phase)
0.5857	Remote Similarity	NPD3932	Clinical (unspecified phase)
0.5851	Remote Similarity	NPD7803	Approved
0.5847	Remote Similarity	NPD4600	Approved
0.5847	Remote Similarity	NPD4601	Approved
0.5833	Remote Similarity	NPD3930	Clinical (unspecified phase)
0.5833	Remote Similarity	NPD6290	Phase 2
0.583	Remote Similarity	NPD7673	Phase 3
0.5821	Remote Similarity	NPD4454	Phase 2
0.5817	Remote Similarity	NPD2721	Clinical (unspecified phase)
0.5816	Remote Similarity	NPD7252	Clinical (unspecified phase)
0.581	Remote Similarity	NPD8399	Phase 1
0.581	Remote Similarity	NPD5658	Approved
0.581	Remote Similarity	NPD8423	Phase 2
0.5806	Remote Similarity	NPD4118	Clinical (unspecified phase)
0.5806	Remote Similarity	NPD1768	Approved
0.5806	Remote Similarity	NPD2176	Approved
0.5806	Remote Similarity	NPD2177	Approved
0.5806	Remote Similarity	NPD2175	Phase 3
0.5804	Remote Similarity	NPD6220	Phase 3
0.5803	Remote Similarity	NPD8358	Approved
0.58	Remote Similarity	NPD3931	Approved
0.58	Remote Similarity	NPD3928	Approved
0.5792	Remote Similarity	NPD6985	Discontinued
0.5789	Remote Similarity	NPD1229	Phase 2
0.5789	Remote Similarity	NPD7688	Phase 1
0.5776	Remote Similarity	NPD5744	Clinical (unspecified phase)
0.5772	Remote Similarity	NPD6491	Clinical (unspecified phase)
0.5769	Remote Similarity	NPD7194	Discontinued
0.5766	Remote Similarity	NPD5807	Phase 2
0.5766	Remote Similarity	NPD7946	Pre-registration
0.5763	Remote Similarity	NPD6160	Clinical (unspecified phase)
0.576	Remote Similarity	NPD6456	Discontinued
0.5759	Remote Similarity	NPD2615	Phase 3
0.5759	Remote Similarity	NPD2616	Phase 3
0.5749	Remote Similarity	NPD5411	Discontinued
0.5748	Remote Similarity	NPD7671	Approved
0.5748	Remote Similarity	NPD7672	Approved
0.5738	Remote Similarity	NPD6281	Approved
0.5737	Remote Similarity	NPD5721	Clinical (unspecified phase)
0.5736	Remote Similarity	NPD4328	Approved
0.5731	Remote Similarity	NPD5530	Phase 1
0.573	Remote Similarity	NPD7921	Approved
0.5725	Remote Similarity	NPD4506	Discontinued
0.572	Remote Similarity	NPD4951	Discontinued
0.5714	Remote Similarity	NPD6642	Approved
0.5714	Remote Similarity	NPD8160	Phase 2
0.5714	Remote Similarity	NPD5612	Discontinued
0.5714	Remote Similarity	NPD6630	Clinical (unspecified phase)
0.5714	Remote Similarity	NPD6641	Approved
0.57	Remote Similarity	NPD8489	Phase 1
0.5698	Remote Similarity	NPD7571	Clinical (unspecified phase)
0.5697	Remote Similarity	NPD4511	Phase 1
0.569	Remote Similarity	NPD3920	Phase 2
0.5687	Remote Similarity	NPD5930	Phase 3
0.5686	Remote Similarity	NPD7947	Clinical (unspecified phase)
0.5685	Remote Similarity	NPD5522	Clinical (unspecified phase)
0.568	Remote Similarity	NPD8396	Approved
0.568	Remote Similarity	NPD8395	Approved
0.5679	Remote Similarity	NPD8442	Discontinued
0.5676	Remote Similarity	NPD7707	Approved
0.5672	Remote Similarity	NPD2380	Approved
0.5672	Remote Similarity	NPD2381	Approved
0.5672	Remote Similarity	NPD2382	Approved
0.5669	Remote Similarity	NPD7958	Clinical (unspecified phase)
0.5669	Remote Similarity	NPD7957	Phase 1
0.5669	Remote Similarity	NPD4901	Clinical (unspecified phase)
0.5664	Remote Similarity	NPD5835	Phase 3
0.5664	Remote Similarity	NPD5834	Phase 3
0.5661	Remote Similarity	NPD5083	Clinical (unspecified phase)
0.5659	Remote Similarity	NPD6657	Clinical (unspecified phase)
0.5657	Remote Similarity	NPD5497	Clinical (unspecified phase)
0.5656	Remote Similarity	NPD8431	Approved
0.5649	Remote Similarity	NPD3258	Approved
0.5647	Remote Similarity	NPD7769	Phase 3
0.5647	Remote Similarity	NPD1392	Approved
0.5642	Remote Similarity	NPD648	Clinical (unspecified phase)
0.5631	Remote Similarity	NPD7181	Phase 3
0.5625	Remote Similarity	NPD8386	Phase 2
0.5625	Remote Similarity	NPD4079	Approved
0.5625	Remote Similarity	NPD4076	Approved
0.5625	Remote Similarity	NPD2739	Clinical (unspecified phase)
0.562	Remote Similarity	NPD5066	Phase 2
0.562	Remote Similarity	NPD5067	Phase 2
0.5607	Remote Similarity	NPD7859	Phase 2
0.5607	Remote Similarity	NPD6375	Clinical (unspecified phase)
0.5606	Remote Similarity	NPD6615	Clinical (unspecified phase)
0.5605	Remote Similarity	NPD4526	Approved
0.5605	Remote Similarity	NPD4528	Approved
0.5605	Remote Similarity	NPD4529	Approved
0.5604	Remote Similarity	NPD3849	Clinical (unspecified phase)
0.5602	Remote Similarity	NPD8464	Clinical (unspecified phase)
0.56	Remote Similarity	NPD7770	Phase 3
0.56	Remote Similarity	NPD6517	Phase 3

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