NPASS Compound

Structure

CID316368 OpenBabel06191716132D 40 45 0 0 1 0 0 0 0 0999 V2000 -2.7395 0.6773 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0267 -0.4817 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6720 -0.9781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.7203 -3.9781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5241 -5.9781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6581 -5.4781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3902 -5.4781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3794 -1.0169 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9400 -0.9781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8060 -2.4781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1222 -5.4781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0485 -0.2738 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8060 -1.4781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.8543 -4.4781 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.6581 -4.4781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0739 -1.4781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4013 -0.8090 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.9400 -2.9781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.9882 -5.9781 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.3902 -4.4781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1222 -4.4781 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.0739 -2.4781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5241 -3.9781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2079 -2.9781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6581 -2.4781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.8543 -5.4781 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.2079 -3.9781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5241 -2.9781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2079 -0.9781 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.9945 0.1045 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6581 -1.4781 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 1.9400 -3.9781 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.9882 -6.9781 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.7203 -5.9781 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.0739 -4.4781 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.3902 -2.4781 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.4945 0.9706 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.9882 -3.9781 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.2562 -3.9781 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 1 12 1 0 0 0 0 2 12 1 0 0 0 0 3 13 1 0 0 0 0 5 6 2 0 0 0 0 5 7 1 0 0 0 0 6 15 1 0 0 0 0 7 20 2 0 0 0 0 8 12 1 0 0 0 0 9 13 2 0 0 0 0 9 16 1 0 0 0 0 10 13 1 0 0 0 0 10 18 2 0 0 0 0 11 19 1 0 0 0 0 11 21 1 0 0 0 0 14 4 1 6 0 0 0 14 26 1 0 0 0 0 14 38 1 0 0 0 0 15 23 2 0 0 0 0 15 27 1 0 0 0 0 16 22 2 0 0 0 0 17 8 1 1 0 0 0 17 30 1 0 0 0 0 17 31 1 0 0 0 0 18 22 1 0 0 0 0 18 32 1 0 0 0 0 19 26 1 0 0 0 0 19 33 1 1 0 0 0 20 23 1 0 0 0 0 20 39 1 0 0 0 0 21 38 1 0 0 0 0 21 39 1 1 0 0 0 22 24 1 0 0 0 0 23 28 1 0 0 0 0 24 25 2 0 0 0 0 24 27 1 0 0 0 0 25 28 1 0 0 0 0 25 31 1 0 0 0 0 26 34 1 1 0 0 0 27 35 2 0 0 0 0 28 36 2 0 0 0 0 29 16 1 1 0 0 0 29 31 1 0 0 0 0 29 40 1 0 0 0 0 30 37 2 0 0 0 0 30 40 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	549.2
Volume:	539.841
LogP:	5.419
LogD:	3.324
LogS:	-4.598
# Rotatable Bonds:	4
TPSA:	154.23
# H-Bond Aceptor:	10
# H-Bond Donor:	5
# Rings:	6
# Heavy Atoms:	10

MedChem Properties

QED Drug-Likeness Score:	0.164
Synthetic Accessibility Score:	4.712
Fsp3:	0.367
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Rejected
Chelating Alert:	1
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.061
MDCK Permeability:	1.0507286788197234e-05
Pgp-inhibitor:	0.104
Pgp-substrate:	0.985
Human Intestinal Absorption (HIA):	0.017
20% Bioavailability (F20%):	0.002
30% Bioavailability (F30%):	0.21

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.008
Plasma Protein Binding (PPB):	94.42005157470703%
Volume Distribution (VD):	0.375
Pgp-substrate:	4.008613586425781%

ADMET: Metabolism

CYP1A2-inhibitor:	0.332
CYP1A2-substrate:	0.132
CYP2C19-inhibitor:	0.064
CYP2C19-substrate:	0.088
CYP2C9-inhibitor:	0.822
CYP2C9-substrate:	0.924
CYP2D6-inhibitor:	0.365
CYP2D6-substrate:	0.167
CYP3A4-inhibitor:	0.106
CYP3A4-substrate:	0.077

ADMET: Excretion

Clearance (CL):	2.258
Half-life (T1/2):	0.414

ADMET: Toxicity

hERG Blockers:	0.01
Human Hepatotoxicity (H-HT):	0.794
Drug-inuced Liver Injury (DILI):	0.971
AMES Toxicity:	0.791
Rat Oral Acute Toxicity:	0.067
Maximum Recommended Daily Dose:	0.993
Skin Sensitization:	0.175
Carcinogencity:	0.967
Eye Corrosion:	0.003
Eye Irritation:	0.13
Respiratory Toxicity:	0.679

Download Data

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

Natural Product: NPC316368

Natural Product ID:	NPC316368
*Common Name:**	Jadomycin L
IUPAC Name:	n.a.
Synonyms:	Jadomycin L
Standard InCHIKey:	WJUCKDQZAWZICN-OTHGIPIRSA-N
Standard InCHI:	InChI=1S/C30H31NO9/c1-12(2)8-17-30(37)40-29-16-9-13(3)10-18(32)22(16)24-25(31(17)29)28(36)23-15(27(24)35)6-5-7-20(23)39-21-11-19(33)26(34)14(4)38-21/h5-7,9-10,12,14,17,19,21,26,29,32-34H,8,11H2,1-4H3/t14-,17-,19+,21-,26-,29-/m0/s1
SMILES:	CC1C(C(CC(O1)OC2=CC=CC3=C2C(=O)C4=C(C3=O)C5=C(C=C(C=C5O)C)C6N4C(C(=O)O6)CC(C)C)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1631685
PubChem CID:	53318487
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0001253] Quinolines and derivatives [CHEMONTID:0001908] Benzoquinolines [CHEMONTID:0000100] Phenanthridines and derivatives

*Note: the InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.
**Note: the Chemical Classification was calculated by NPClassifier Version 1.5. Reference: PMID:34662515.

Species Source

Organism ID	Organism Name	Taxonomy Level	Family	SuperKingdom	Isolation Part	Collection Location	Collection Time	Reference
NPO28993	Streptomyces venezuelae	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[11720530]
NPO28993	Streptomyces venezuelae	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[16724858]
NPO28993	Streptomyces venezuelae	Species	Streptomycetaceae	Bacteria	n.a.	Guam Island, Pacific Ocean	n.a.	PMID[21774474]
NPO28993	Streptomyces venezuelae	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[22050382]
NPO28993	Streptomyces venezuelae	Species	Streptomycetaceae	Bacteria	n.a.	Guam Island, Pacific Ocean	n.a.	PMID[23164710]
NPO28993	Streptomyces venezuelae	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[26203536]
NPO28993	Streptomyces venezuelae	Species	Streptomycetaceae	Bacteria	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
GI50	1
MIC	14
Others	2

Activity Type	# Activity
NON-MOLECULAR	3
Organism	14

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	<	1.0	ug.mL-1	PMID[540269]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	=	8.0	ug.mL-1	PMID[540269]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	=	16.0	ug.mL-1	PMID[540269]
NPT17	Organism	Staphylococcus epidermidis	Staphylococcus epidermidis	MIC	<	1.0	ug.mL-1	PMID[540269]
NPT17	Organism	Staphylococcus epidermidis	Staphylococcus epidermidis	MIC	=	4.0	ug.mL-1	PMID[540269]
NPT18	Organism	Pseudomonas aeruginosa	Pseudomonas aeruginosa	MIC	<	128.0	ug.mL-1	PMID[540269]
NPT175	Organism	Enterococcus faecalis	Enterococcus faecalis	MIC	<	128.0	ug.mL-1	PMID[540269]
NPT79	Organism	Bacillus subtilis	Bacillus subtilis	MIC	=	16.0	ug.mL-1	PMID[540269]
NPT17	Organism	Staphylococcus epidermidis	Staphylococcus epidermidis	MIC	=	0.5	ug.mL-1	PMID[540269]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	GI50	=	1820.0	nM	PMID[540270]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	TGI	=	4100.0	nM	PMID[540270]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	LC50	=	9300.0	nM	PMID[540270]

☑ 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 NPC316368 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	307
0.1-0.2	1303
0.2-0.3	3128
0.3-0.4	9151
0.4-0.5	9740
0.5-0.6	8738
0.6-0.7	9725
0.7-0.8	589
0.8-0.85	5
0.85-0.9	0
0.9-0.95	0
0.95-1	11

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC284236
0.9948	High Similarity	NPC321226
0.9948	High Similarity	NPC328856
0.9948	High Similarity	NPC478047
0.9948	High Similarity	NPC180210
0.9948	High Similarity	NPC478046
0.9948	High Similarity	NPC314914
0.9896	High Similarity	NPC478048
0.9796	High Similarity	NPC170101
0.8104	Intermediate Similarity	NPC315253
0.8088	Intermediate Similarity	NPC42286
0.7981	Intermediate Similarity	NPC314941
0.7973	Intermediate Similarity	NPC316292
0.7943	Intermediate Similarity	NPC314946
0.7938	Intermediate Similarity	NPC178281
0.7867	Intermediate Similarity	NPC315889
0.7857	Intermediate Similarity	NPC63470
0.7835	Intermediate Similarity	NPC212099
0.7835	Intermediate Similarity	NPC101116
0.7835	Intermediate Similarity	NPC278329
0.7835	Intermediate Similarity	NPC146837
0.7826	Intermediate Similarity	NPC313453
0.7793	Intermediate Similarity	NPC315914
0.7788	Intermediate Similarity	NPC313274
0.7778	Intermediate Similarity	NPC215098
0.7778	Intermediate Similarity	NPC124302
0.7778	Intermediate Similarity	NPC316412
0.7778	Intermediate Similarity	NPC46744
0.7778	Intermediate Similarity	NPC14622
0.7778	Intermediate Similarity	NPC73020
0.7778	Intermediate Similarity	NPC70290
0.7778	Intermediate Similarity	NPC315351
0.7778	Intermediate Similarity	NPC83019
0.7751	Intermediate Similarity	NPC316164
0.7729	Intermediate Similarity	NPC204580
0.7727	Intermediate Similarity	NPC246274
0.7706	Intermediate Similarity	NPC313582
0.7703	Intermediate Similarity	NPC109403
0.7703	Intermediate Similarity	NPC261012
0.7703	Intermediate Similarity	NPC226652
0.7703	Intermediate Similarity	NPC120671
0.7703	Intermediate Similarity	NPC314100
0.7703	Intermediate Similarity	NPC314738
0.7703	Intermediate Similarity	NPC72788
0.77	Intermediate Similarity	NPC203751
0.77	Intermediate Similarity	NPC257728
0.77	Intermediate Similarity	NPC85368
0.7696	Intermediate Similarity	NPC469437
0.7689	Intermediate Similarity	NPC80472
0.7685	Intermediate Similarity	NPC475161
0.7685	Intermediate Similarity	NPC477860
0.7664	Intermediate Similarity	NPC153365
0.7662	Intermediate Similarity	NPC68381
0.7662	Intermediate Similarity	NPC470667
0.7662	Intermediate Similarity	NPC223735
0.7662	Intermediate Similarity	NPC186800
0.7662	Intermediate Similarity	NPC307754
0.7653	Intermediate Similarity	NPC257266
0.765	Intermediate Similarity	NPC315619
0.763	Intermediate Similarity	NPC2173
0.763	Intermediate Similarity	NPC202771
0.763	Intermediate Similarity	NPC328700
0.763	Intermediate Similarity	NPC119818
0.7624	Intermediate Similarity	NPC102053
0.7624	Intermediate Similarity	NPC76112
0.7624	Intermediate Similarity	NPC92403
0.7624	Intermediate Similarity	NPC475246
0.7624	Intermediate Similarity	NPC66820
0.7624	Intermediate Similarity	NPC289876
0.7624	Intermediate Similarity	NPC475233
0.7624	Intermediate Similarity	NPC170018
0.7613	Intermediate Similarity	NPC252156
0.7612	Intermediate Similarity	NPC199357
0.7596	Intermediate Similarity	NPC33256
0.7574	Intermediate Similarity	NPC3718
0.757	Intermediate Similarity	NPC314596
0.7563	Intermediate Similarity	NPC97637
0.7563	Intermediate Similarity	NPC187934
0.7563	Intermediate Similarity	NPC216752
0.7562	Intermediate Similarity	NPC30432
0.7562	Intermediate Similarity	NPC271385
0.7562	Intermediate Similarity	NPC111536
0.7562	Intermediate Similarity	NPC76128
0.7562	Intermediate Similarity	NPC5029
0.755	Intermediate Similarity	NPC191653
0.7549	Intermediate Similarity	NPC277710
0.7549	Intermediate Similarity	NPC153578
0.7549	Intermediate Similarity	NPC299149
0.7549	Intermediate Similarity	NPC114257
0.7549	Intermediate Similarity	NPC58538
0.7537	Intermediate Similarity	NPC198893
0.7537	Intermediate Similarity	NPC232818
0.7537	Intermediate Similarity	NPC46958
0.7537	Intermediate Similarity	NPC314489
0.7536	Intermediate Similarity	NPC105591
0.7536	Intermediate Similarity	NPC226708
0.7525	Intermediate Similarity	NPC98776
0.7524	Intermediate Similarity	NPC166979
0.7512	Intermediate Similarity	NPC298778
0.7512	Intermediate Similarity	NPC197357
0.7512	Intermediate Similarity	NPC85316
0.75	Intermediate Similarity	NPC185031
0.75	Intermediate Similarity	NPC205721
0.7488	Intermediate Similarity	NPC199533
0.7488	Intermediate Similarity	NPC470454
0.7488	Intermediate Similarity	NPC63105
0.7488	Intermediate Similarity	NPC474345
0.7487	Intermediate Similarity	NPC148323
0.7487	Intermediate Similarity	NPC283480
0.7465	Intermediate Similarity	NPC286135
0.7464	Intermediate Similarity	NPC314672
0.7463	Intermediate Similarity	NPC222455
0.7463	Intermediate Similarity	NPC245059
0.7463	Intermediate Similarity	NPC259905
0.7463	Intermediate Similarity	NPC84494
0.7449	Intermediate Similarity	NPC208651
0.7449	Intermediate Similarity	NPC206641
0.744	Intermediate Similarity	NPC224557
0.744	Intermediate Similarity	NPC292706
0.7438	Intermediate Similarity	NPC213052
0.7438	Intermediate Similarity	NPC309692
0.7438	Intermediate Similarity	NPC472054
0.7437	Intermediate Similarity	NPC17432
0.7436	Intermediate Similarity	NPC192219
0.7436	Intermediate Similarity	NPC82190
0.7436	Intermediate Similarity	NPC174599
0.7427	Intermediate Similarity	NPC18306
0.7427	Intermediate Similarity	NPC470448
0.7427	Intermediate Similarity	NPC470452
0.7427	Intermediate Similarity	NPC164047
0.7427	Intermediate Similarity	NPC470453
0.7416	Intermediate Similarity	NPC94499
0.7412	Intermediate Similarity	NPC211215
0.7411	Intermediate Similarity	NPC53139
0.7406	Intermediate Similarity	NPC267414
0.7406	Intermediate Similarity	NPC478045
0.7406	Intermediate Similarity	NPC207239
0.7404	Intermediate Similarity	NPC87583
0.74	Intermediate Similarity	NPC478022
0.74	Intermediate Similarity	NPC478020
0.74	Intermediate Similarity	NPC99216
0.74	Intermediate Similarity	NPC478026
0.7391	Intermediate Similarity	NPC478001
0.7391	Intermediate Similarity	NPC473631
0.7391	Intermediate Similarity	NPC473717
0.7391	Intermediate Similarity	NPC475662
0.7391	Intermediate Similarity	NPC162694
0.7391	Intermediate Similarity	NPC293227
0.7389	Intermediate Similarity	NPC478002
0.7385	Intermediate Similarity	NPC209393
0.7385	Intermediate Similarity	NPC205172
0.7381	Intermediate Similarity	NPC469816
0.7381	Intermediate Similarity	NPC469815
0.7379	Intermediate Similarity	NPC212290
0.7374	Intermediate Similarity	NPC328093
0.7371	Intermediate Similarity	NPC108487
0.7366	Intermediate Similarity	NPC312630
0.7366	Intermediate Similarity	NPC324220
0.7363	Intermediate Similarity	NPC178851
0.736	Intermediate Similarity	NPC29552
0.736	Intermediate Similarity	NPC177742
0.7358	Intermediate Similarity	NPC314020
0.7347	Intermediate Similarity	NPC3449
0.7346	Intermediate Similarity	NPC308895
0.7346	Intermediate Similarity	NPC48474
0.7339	Intermediate Similarity	NPC46990
0.733	Intermediate Similarity	NPC478000
0.7321	Intermediate Similarity	NPC475352
0.7321	Intermediate Similarity	NPC475220
0.7321	Intermediate Similarity	NPC473686
0.7321	Intermediate Similarity	NPC229817
0.7321	Intermediate Similarity	NPC241847
0.7321	Intermediate Similarity	NPC221140
0.7317	Intermediate Similarity	NPC146803
0.7317	Intermediate Similarity	NPC193377
0.7313	Intermediate Similarity	NPC474301
0.7311	Intermediate Similarity	NPC24228
0.7304	Intermediate Similarity	NPC183441
0.7302	Intermediate Similarity	NPC131405
0.73	Intermediate Similarity	NPC22324
0.7296	Intermediate Similarity	NPC470331
0.7296	Intermediate Similarity	NPC185103
0.7295	Intermediate Similarity	NPC474746
0.7295	Intermediate Similarity	NPC475981
0.7291	Intermediate Similarity	NPC473202
0.729	Intermediate Similarity	NPC133775
0.7286	Intermediate Similarity	NPC174486
0.7282	Intermediate Similarity	NPC475054
0.7273	Intermediate Similarity	NPC106700
0.7273	Intermediate Similarity	NPC141440
0.7268	Intermediate Similarity	NPC316539
0.7264	Intermediate Similarity	NPC477258
0.7264	Intermediate Similarity	NPC125924
0.726	Intermediate Similarity	NPC170203
0.726	Intermediate Similarity	NPC315221
0.7257	Intermediate Similarity	NPC148124
0.7255	Intermediate Similarity	NPC477573
0.7255	Intermediate Similarity	NPC76047
0.7255	Intermediate Similarity	NPC478021
0.7255	Intermediate Similarity	NPC52598

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 NPC316368 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	198
0.1-0.2	558
0.2-0.3	1061
0.3-0.4	2113
0.4-0.5	2724
0.5-0.6	1811
0.6-0.7	604
0.7-0.8	77
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
0.8093	Intermediate Similarity	NPD8155	Clinical (unspecified phase)
0.8038	Intermediate Similarity	NPD7701	Phase 2
0.7981	Intermediate Similarity	NPD8319	Approved
0.7981	Intermediate Similarity	NPD8320	Phase 1
0.7778	Intermediate Similarity	NPD4420	Approved
0.7736	Intermediate Similarity	NPD7584	Approved
0.7703	Intermediate Similarity	NPD6782	Approved
0.7703	Intermediate Similarity	NPD6778	Approved
0.7703	Intermediate Similarity	NPD6777	Approved
0.7703	Intermediate Similarity	NPD6776	Approved
0.7703	Intermediate Similarity	NPD6781	Approved
0.7703	Intermediate Similarity	NPD6779	Approved
0.7703	Intermediate Similarity	NPD6780	Approved
0.77	Intermediate Similarity	NPD7585	Approved
0.7674	Intermediate Similarity	NPD7783	Phase 2
0.7674	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7653	Intermediate Similarity	NPD7583	Approved
0.763	Intermediate Similarity	NPD5005	Approved
0.763	Intermediate Similarity	NPD5006	Approved
0.7628	Intermediate Similarity	NPD7874	Approved
0.7628	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7624	Intermediate Similarity	NPD8312	Approved
0.7624	Intermediate Similarity	NPD8313	Approved
0.7613	Intermediate Similarity	NPD5619	Clinical (unspecified phase)
0.7594	Intermediate Similarity	NPD7696	Phase 3
0.7594	Intermediate Similarity	NPD7698	Approved
0.7594	Intermediate Similarity	NPD7697	Approved
0.7581	Intermediate Similarity	NPD8151	Discontinued
0.7574	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7573	Intermediate Similarity	NPD3808	Clinical (unspecified phase)
0.7569	Intermediate Similarity	NPD7930	Approved
0.7559	Intermediate Similarity	NPD7871	Phase 2
0.7559	Intermediate Similarity	NPD7870	Phase 2
0.7512	Intermediate Similarity	NPD7801	Approved
0.7511	Intermediate Similarity	NPD8059	Phase 3
0.7511	Intermediate Similarity	NPD8058	Clinical (unspecified phase)
0.7488	Intermediate Similarity	NPD8285	Discontinued
0.7465	Intermediate Similarity	NPD6823	Phase 2
0.7464	Intermediate Similarity	NPD6535	Approved
0.7464	Intermediate Similarity	NPD6534	Approved
0.7442	Intermediate Similarity	NPD7211	Clinical (unspecified phase)
0.743	Intermediate Similarity	NPD7435	Discontinued
0.7421	Intermediate Similarity	NPD8404	Phase 2
0.7416	Intermediate Similarity	NPD6212	Phase 3
0.7416	Intermediate Similarity	NPD6214	Clinical (unspecified phase)
0.7416	Intermediate Similarity	NPD6213	Phase 3
0.7368	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7361	Intermediate Similarity	NPD7999	Approved
0.7358	Intermediate Similarity	NPD7700	Phase 2
0.7358	Intermediate Similarity	NPD7699	Phase 2
0.7356	Intermediate Similarity	NPD7235	Clinical (unspecified phase)
0.7324	Intermediate Similarity	NPD7565	Approved
0.7313	Intermediate Similarity	NPD8491	Approved
0.7289	Intermediate Similarity	NPD8366	Approved
0.7273	Intermediate Similarity	NPD8461	Discontinued
0.7268	Intermediate Similarity	NPD6559	Discontinued
0.7257	Intermediate Similarity	NPD6997	Phase 2
0.7241	Intermediate Similarity	NPD7177	Discontinued
0.7214	Intermediate Similarity	NPD5711	Approved
0.7214	Intermediate Similarity	NPD5710	Approved
0.7209	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7205	Intermediate Similarity	NPD8469	Approved
0.7183	Intermediate Similarity	NPD7667	Clinical (unspecified phase)
0.7183	Intermediate Similarity	NPD4361	Phase 2
0.7183	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.7179	Intermediate Similarity	NPD7048	Phase 3
0.7163	Intermediate Similarity	NPD6874	Approved
0.7137	Intermediate Similarity	NPD7907	Approved
0.7124	Intermediate Similarity	NPD4665	Approved
0.7124	Intermediate Similarity	NPD4111	Phase 1
0.7107	Intermediate Similarity	NPD5889	Approved
0.7107	Intermediate Similarity	NPD5890	Approved
0.71	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7095	Intermediate Similarity	NPD8150	Discontinued
0.7091	Intermediate Similarity	NPD6973	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD7810	Phase 3
0.7083	Intermediate Similarity	NPD7811	Phase 3
0.7073	Intermediate Similarity	NPD3818	Discontinued
0.7073	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.7071	Intermediate Similarity	NPD6844	Discontinued
0.707	Intermediate Similarity	NPD7238	Clinical (unspecified phase)
0.7056	Intermediate Similarity	NPD4360	Phase 2
0.7056	Intermediate Similarity	NPD4363	Phase 3
0.704	Intermediate Similarity	NPD5676	Approved
0.7039	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7028	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7018	Intermediate Similarity	NPD3450	Approved
0.7018	Intermediate Similarity	NPD3452	Approved
0.7018	Intermediate Similarity	NPD2493	Approved
0.7018	Intermediate Similarity	NPD2494	Approved
0.7015	Intermediate Similarity	NPD8005	Clinical (unspecified phase)
0.7014	Intermediate Similarity	NPD3863	Clinical (unspecified phase)
0.7005	Intermediate Similarity	NPD3226	Approved
0.7	Intermediate Similarity	NPD4582	Approved
0.7	Intermediate Similarity	NPD4583	Approved
0.6986	Remote Similarity	NPD5034	Approved
0.6986	Remote Similarity	NPD4954	Approved
0.6986	Remote Similarity	NPD3057	Approved
0.6986	Remote Similarity	NPD5026	Approved
0.6986	Remote Similarity	NPD4955	Approved
0.6986	Remote Similarity	NPD5028	Approved
0.6986	Remote Similarity	NPD36	Approved
0.6979	Remote Similarity	NPD6625	Approved
0.6976	Remote Similarity	NPD3451	Clinical (unspecified phase)
0.697	Remote Similarity	NPD6585	Discontinued
0.6966	Remote Similarity	NPD8067	Phase 3
0.6957	Remote Similarity	NPD3050	Clinical (unspecified phase)
0.6957	Remote Similarity	NPD7054	Approved
0.6955	Remote Similarity	NPD4004	Approved
0.6955	Remote Similarity	NPD4002	Approved
0.6955	Remote Similarity	NPD8152	Approved
0.6955	Remote Similarity	NPD8153	Approved
0.6946	Remote Similarity	NPD4666	Phase 3
0.6943	Remote Similarity	NPD5433	Clinical (unspecified phase)
0.6942	Remote Similarity	NPD3446	Phase 1
0.6938	Remote Similarity	NPD5030	Phase 2
0.6934	Remote Similarity	NPD5038	Approved
0.6934	Remote Similarity	NPD5037	Approved
0.6927	Remote Similarity	NPD5242	Approved
0.6923	Remote Similarity	NPD7074	Phase 3
0.6923	Remote Similarity	NPD7472	Approved
0.6912	Remote Similarity	NPD2974	Approved
0.6912	Remote Similarity	NPD2975	Approved
0.6912	Remote Similarity	NPD2973	Approved
0.6909	Remote Similarity	NPD2972	Approved
0.6909	Remote Similarity	NPD2491	Approved
0.6909	Remote Similarity	NPD3448	Approved
0.6909	Remote Similarity	NPD3533	Approved
0.6905	Remote Similarity	NPD4338	Clinical (unspecified phase)
0.6897	Remote Similarity	NPD5709	Phase 3
0.6895	Remote Similarity	NPD4580	Approved
0.6895	Remote Similarity	NPD4107	Approved
0.6895	Remote Similarity	NPD5457	Discontinued
0.6892	Remote Similarity	NPD8161	Suspended
0.689	Remote Similarity	NPD6797	Phase 2
0.689	Remote Similarity	NPD3823	Discontinued
0.6887	Remote Similarity	NPD5036	Approved
0.6878	Remote Similarity	NPD7597	Clinical (unspecified phase)
0.6869	Remote Similarity	NPD8361	Approved
0.6869	Remote Similarity	NPD8360	Approved
0.6857	Remote Similarity	NPD7039	Approved
0.6857	Remote Similarity	NPD7251	Discontinued
0.6857	Remote Similarity	NPD7038	Approved
0.6853	Remote Similarity	NPD6090	Discontinued
0.6842	Remote Similarity	NPD7047	Phase 3
0.6842	Remote Similarity	NPD8492	Approved
0.6837	Remote Similarity	NPD2490	Approved
0.6837	Remote Similarity	NPD2488	Approved
0.6834	Remote Similarity	NPD6591	Clinical (unspecified phase)
0.6833	Remote Similarity	NPD6863	Phase 2
0.6832	Remote Similarity	NPD5616	Clinical (unspecified phase)
0.6825	Remote Similarity	NPD7808	Phase 3
0.6816	Remote Similarity	NPD8367	Approved
0.6812	Remote Similarity	NPD4575	Clinical (unspecified phase)
0.6806	Remote Similarity	NPD5968	Phase 3
0.6806	Remote Similarity	NPD7296	Approved
0.68	Remote Similarity	NPD4380	Phase 2
0.6795	Remote Similarity	NPD7186	Phase 3
0.6791	Remote Similarity	NPD6836	Approved
0.6791	Remote Similarity	NPD8435	Approved
0.6788	Remote Similarity	NPD2346	Discontinued
0.6787	Remote Similarity	NPD4482	Phase 3
0.6787	Remote Similarity	NPD7566	Clinical (unspecified phase)
0.6782	Remote Similarity	NPD7819	Suspended
0.6779	Remote Similarity	NPD7473	Discontinued
0.6766	Remote Similarity	NPD6386	Approved
0.6766	Remote Similarity	NPD6385	Approved
0.6765	Remote Similarity	NPD7075	Discontinued
0.6761	Remote Similarity	NPD7090	Clinical (unspecified phase)
0.6757	Remote Similarity	NPD8163	Clinical (unspecified phase)
0.6757	Remote Similarity	NPD8162	Phase 2
0.6756	Remote Similarity	NPD6593	Clinical (unspecified phase)
0.675	Remote Similarity	NPD2651	Approved
0.675	Remote Similarity	NPD2649	Approved
0.6749	Remote Similarity	NPD5402	Approved
0.6748	Remote Similarity	NPD6959	Discontinued
0.6746	Remote Similarity	NPD7228	Approved
0.6742	Remote Similarity	NPD8486	Clinical (unspecified phase)
0.6735	Remote Similarity	NPD3295	Clinical (unspecified phase)
0.6731	Remote Similarity	NPD7784	Clinical (unspecified phase)
0.6715	Remote Similarity	NPD6808	Phase 2
0.6715	Remote Similarity	NPD6232	Discontinued
0.6714	Remote Similarity	NPD5844	Phase 1
0.6712	Remote Similarity	NPD7476	Discontinued
0.6711	Remote Similarity	NPD7827	Phase 1
0.6698	Remote Similarity	NPD5031	Approved
0.6698	Remote Similarity	NPD8434	Phase 2
0.6698	Remote Similarity	NPD5029	Approved
0.6698	Remote Similarity	NPD5027	Approved
0.6698	Remote Similarity	NPD8424	Clinical (unspecified phase)
0.6683	Remote Similarity	NPD2970	Approved
0.6683	Remote Similarity	NPD2969	Approved
0.6682	Remote Similarity	NPD5441	Clinical (unspecified phase)
0.6681	Remote Similarity	NPD4859	Phase 1
0.6667	Remote Similarity	NPD7256	Discontinued
0.6667	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD5978	Approved
0.6667	Remote Similarity	NPD5977	Approved
0.6667	Remote Similarity	NPD7906	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