NPASS Compound

Structure

NPC19170 OpenBabel07101719522D 51 57 0 0 1 0 0 0 0 0999 V2000 6.8556 -1.4016 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.2068 1.8345 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 7.0820 -1.4105 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9131 1.7226 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.7302 -1.4704 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5000 -1.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9262 3.1921 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.9540 -0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.9540 -1.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0352 2.7381 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.7649 2.6474 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0880 -0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0880 -2.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9829 1.7394 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.4074 1.0981 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9657 0.0507 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6831 0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.9393 0.5186 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0000 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.4197 0.9417 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.7126 1.6488 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2219 -0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2219 -1.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8216 1.1948 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6831 -1.3090 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 7.6245 1.1300 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 8.4379 -0.6971 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2709 -0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 7.0367 0.3210 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.7321 0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 9.0257 0.1119 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0000 -1.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.2709 -2.1180 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 7.4434 -0.5926 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 8.6190 1.0255 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -0.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 3.9780 0.2071 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -1.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 10.7483 -0.0691 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.5000 -0.1340 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 7.2177 2.0435 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 8.8447 -1.6107 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.5595 -0.5578 0.0000 S 0 0 0 0 0 0 0 0 0 0 0 0 1.3253 0.9135 0.0000 S 0 0 0 0 0 0 0 0 0 0 0 0 9.8347 -0.4759 0.0000 S 0 0 0 0 0 0 0 0 0 0 0 0 -0.5000 -1.8660 0.0000 S 0 0 0 0 0 0 0 0 0 0 0 0 1 37 1 0 0 0 0 2 38 1 0 0 0 0 3 39 1 0 0 0 0 4 48 1 0 0 0 0 5 49 1 0 0 0 0 6 50 1 0 0 0 0 7 51 1 0 0 0 0 8 11 2 0 0 0 0 8 12 1 0 0 0 0 9 10 2 0 0 0 0 9 13 1 0 0 0 0 10 14 1 0 0 0 0 11 15 1 0 0 0 0 12 22 2 0 0 0 0 13 23 2 0 0 0 0 14 24 2 0 0 0 0 15 25 2 0 0 0 0 16 21 1 0 0 0 0 17 21 2 0 0 0 0 17 40 1 0 0 0 0 18 33 1 0 0 0 0 19 42 1 0 0 0 0 20 43 1 0 0 0 0 21 22 1 0 0 0 0 22 25 1 0 0 0 0 23 24 1 0 0 0 0 23 31 1 0 0 0 0 24 36 1 0 0 0 0 25 40 1 0 0 0 0 26 31 1 6 0 0 0 26 36 1 0 0 0 0 26 41 1 0 0 0 0 27 32 1 0 0 0 0 27 38 1 0 0 0 0 27 44 2 0 0 0 0 28 33 1 0 0 0 0 28 39 1 0 0 0 0 28 45 2 0 0 0 0 29 34 1 0 0 0 0 29 37 1 0 0 0 0 29 46 2 0 0 0 0 30 35 1 0 0 0 0 30 41 1 0 0 0 0 30 47 2 0 0 0 0 31 18 1 6 0 0 0 31 40 1 0 0 0 0 32 16 1 6 0 0 0 32 37 1 0 0 0 0 32 48 1 0 0 0 0 33 41 1 0 0 0 0 33 49 1 6 0 0 0 34 19 1 6 0 0 0 34 38 1 0 0 0 0 34 50 1 0 0 0 0 35 20 1 1 0 0 0 35 39 1 0 0 0 0 35 51 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	770.2
Volume:	717.778
LogP:	4.774
LogD:	2.148
LogS:	-4.744
# Rotatable Bonds:	9
TPSA:	138.66
# H-Bond Aceptor:	12
# H-Bond Donor:	3
# Rings:	7
# Heavy Atoms:	16

MedChem Properties

QED Drug-Likeness Score:	0.296
Synthetic Accessibility Score:	5.949
Fsp3:	0.486
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:	-5.536
MDCK Permeability:	8.360837455256842e-06
Pgp-inhibitor:	0.811
Pgp-substrate:	0.968
Human Intestinal Absorption (HIA):	0.67
20% Bioavailability (F20%):	0.008
30% Bioavailability (F30%):	0.056

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.227
Plasma Protein Binding (PPB):	95.93021392822266%
Volume Distribution (VD):	1.705
Pgp-substrate:	2.08379864692688%

ADMET: Metabolism

CYP1A2-inhibitor:	0.019
CYP1A2-substrate:	0.666
CYP2C19-inhibitor:	0.967
CYP2C19-substrate:	0.973
CYP2C9-inhibitor:	0.967
CYP2C9-substrate:	0.092
CYP2D6-inhibitor:	0.041
CYP2D6-substrate:	0.015
CYP3A4-inhibitor:	0.978
CYP3A4-substrate:	0.994

ADMET: Excretion

Clearance (CL):	6.668
Half-life (T1/2):	0.006

ADMET: Toxicity

hERG Blockers:	0.0
Human Hepatotoxicity (H-HT):	0.302
Drug-inuced Liver Injury (DILI):	0.987
AMES Toxicity:	0.004
Rat Oral Acute Toxicity:	0.751
Maximum Recommended Daily Dose:	0.011
Skin Sensitization:	0.797
Carcinogencity:	0.41
Eye Corrosion:	0.003
Eye Irritation:	0.004
Respiratory Toxicity:	0.0

Download Data

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

Natural Product: NPC19170

Natural Product ID:	NPC19170
*Common Name:**	YDUJBQZOCBSEQA-JLYHLUBJSA-N
IUPAC Name:	n.a.
Synonyms:	Dethio-Tetra(Methylthio) Chetomin
Standard InCHIKey:	YDUJBQZOCBSEQA-JLYHLUBJSA-N
Standard InCHI:	InChI=1S/C35H42N6O6S4/c1-37-29(46)34(19-42,50-6)38(2)27(44)32(37,48-4)16-21-17-40(25-15-11-8-12-22(21)25)31-18-33(49-5)28(45)39(3)35(20-43,51-7)30(47)41(33)26(31)36-24-14-10-9-13-23(24)31/h8-15,17,26,36,42-43H,16,18-20H2,1-7H3/t26-,31+,32+,33+,34+,35+/m1/s1
SMILES:	CS[C@]1(Cc2cn(c3c2cccc3)[C@@]23C[C@]4(N([C@H]3Nc3c2cccc3)C(=O)[C@](N(C4=O)C)(CO)SC)SC)N(C)C(=O)[C@](N(C1=O)C)(CO)SC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL510163
PubChem CID:	16040180
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000211] Indoles and derivatives [CHEMONTID:0001733] Pyrroloindoles

*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
NPO9444	Chaetomium cochliodes	Species	Chaetomiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16989540]
NPO9444	Chaetomium cochliodes	Species	Chaetomiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[32115958]
NPO9444	Chaetomium cochliodes	Species	Chaetomiaceae	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
GI50	3

Activity Type	# Activity
NON-MOLECULAR	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	GI50	=	0.06	ug.mL-1	PMID[545974]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	GI50	=	0.05	ug.mL-1	PMID[545974]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	GI50	=	0.2	ug.mL-1	PMID[545974]

☑ 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 NPC19170 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	401
0.1-0.2	3374
0.2-0.3	22927
0.3-0.4	9785
0.4-0.5	2340
0.5-0.6	2574
0.6-0.7	1137
0.7-0.8	137
0.8-0.85	11
0.85-0.9	5
0.9-0.95	3
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9851	High Similarity	NPC297862
0.9604	High Similarity	NPC253987
0.9412	High Similarity	NPC327095
0.9412	High Similarity	NPC312942
0.9366	High Similarity	NPC40455
0.9118	High Similarity	NPC470731
0.9087	High Similarity	NPC476817
0.8841	High Similarity	NPC470732
0.875	High Similarity	NPC63279
0.871	High Similarity	NPC297642
0.8657	High Similarity	NPC475859
0.8657	High Similarity	NPC475969
0.8618	High Similarity	NPC165743
0.8611	High Similarity	NPC477175
0.8611	High Similarity	NPC470730
0.8402	Intermediate Similarity	NPC474877
0.8402	Intermediate Similarity	NPC477177
0.8356	Intermediate Similarity	NPC477176
0.8356	Intermediate Similarity	NPC470729
0.8098	Intermediate Similarity	NPC294693
0.7934	Intermediate Similarity	NPC54420
0.786	Intermediate Similarity	NPC162860
0.7671	Intermediate Similarity	NPC31385
0.7671	Intermediate Similarity	NPC75726
0.7671	Intermediate Similarity	NPC110602
0.7642	Intermediate Similarity	NPC171317
0.7615	Intermediate Similarity	NPC223791
0.7615	Intermediate Similarity	NPC107077
0.7569	Intermediate Similarity	NPC470491
0.756	Intermediate Similarity	NPC128582
0.7559	Intermediate Similarity	NPC473640
0.7543	Intermediate Similarity	NPC478028
0.7535	Intermediate Similarity	NPC475506
0.7534	Intermediate Similarity	NPC478158
0.7522	Intermediate Similarity	NPC31097
0.7511	Intermediate Similarity	NPC75634
0.75	Intermediate Similarity	NPC155143
0.75	Intermediate Similarity	NPC94752
0.75	Intermediate Similarity	NPC477714
0.7479	Intermediate Similarity	NPC478029
0.7478	Intermediate Similarity	NPC474896
0.7464	Intermediate Similarity	NPC17059
0.7463	Intermediate Similarity	NPC11126
0.7455	Intermediate Similarity	NPC477715
0.7444	Intermediate Similarity	NPC478157
0.7435	Intermediate Similarity	NPC191382
0.7435	Intermediate Similarity	NPC56109
0.7434	Intermediate Similarity	NPC272174
0.7431	Intermediate Similarity	NPC473376
0.7422	Intermediate Similarity	NPC281049
0.7404	Intermediate Similarity	NPC228835
0.7368	Intermediate Similarity	NPC99939
0.7368	Intermediate Similarity	NPC155444
0.7368	Intermediate Similarity	NPC308931
0.7361	Intermediate Similarity	NPC100321
0.7353	Intermediate Similarity	NPC161861
0.7346	Intermediate Similarity	NPC213629
0.7328	Intermediate Similarity	NPC69843
0.7321	Intermediate Similarity	NPC54744
0.7309	Intermediate Similarity	NPC320968
0.7277	Intermediate Similarity	NPC117244
0.7277	Intermediate Similarity	NPC473763
0.7251	Intermediate Similarity	NPC135601
0.7251	Intermediate Similarity	NPC17273
0.7251	Intermediate Similarity	NPC141612
0.7243	Intermediate Similarity	NPC14812
0.7202	Intermediate Similarity	NPC293917
0.7186	Intermediate Similarity	NPC64216
0.7177	Intermediate Similarity	NPC16659
0.7175	Intermediate Similarity	NPC471945
0.7175	Intermediate Similarity	NPC475259
0.7175	Intermediate Similarity	NPC471950
0.7163	Intermediate Similarity	NPC471386
0.7157	Intermediate Similarity	NPC56233
0.7149	Intermediate Similarity	NPC477179
0.7149	Intermediate Similarity	NPC317701
0.7143	Intermediate Similarity	NPC28945
0.7143	Intermediate Similarity	NPC471946
0.7143	Intermediate Similarity	NPC471951
0.7129	Intermediate Similarity	NPC265710
0.7119	Intermediate Similarity	NPC89987
0.7117	Intermediate Similarity	NPC477181
0.7117	Intermediate Similarity	NPC254850
0.7117	Intermediate Similarity	NPC477178
0.7117	Intermediate Similarity	NPC477180
0.7109	Intermediate Similarity	NPC314176
0.7103	Intermediate Similarity	NPC255909
0.7103	Intermediate Similarity	NPC103119
0.7095	Intermediate Similarity	NPC91179
0.7094	Intermediate Similarity	NPC476491
0.7085	Intermediate Similarity	NPC477174
0.7085	Intermediate Similarity	NPC470490
0.7085	Intermediate Similarity	NPC477173
0.7081	Intermediate Similarity	NPC473380
0.7081	Intermediate Similarity	NPC240088
0.7073	Intermediate Similarity	NPC153400
0.707	Intermediate Similarity	NPC478011
0.707	Intermediate Similarity	NPC478012
0.7067	Intermediate Similarity	NPC469938
0.7063	Intermediate Similarity	NPC314056
0.7063	Intermediate Similarity	NPC263117
0.7063	Intermediate Similarity	NPC125181
0.7063	Intermediate Similarity	NPC242872
0.7059	Intermediate Similarity	NPC325976
0.7054	Intermediate Similarity	NPC323927
0.7054	Intermediate Similarity	NPC470488
0.7051	Intermediate Similarity	NPC304203
0.7037	Intermediate Similarity	NPC476460
0.7035	Intermediate Similarity	NPC475359
0.7035	Intermediate Similarity	NPC191817
0.7031	Intermediate Similarity	NPC471192
0.7028	Intermediate Similarity	NPC163055
0.7027	Intermediate Similarity	NPC182507
0.7023	Intermediate Similarity	NPC321708
0.7017	Intermediate Similarity	NPC220852
0.7014	Intermediate Similarity	NPC24864
0.7005	Intermediate Similarity	NPC91895
0.7	Intermediate Similarity	NPC238945
0.7	Intermediate Similarity	NPC474389
0.7	Intermediate Similarity	NPC285343
0.698	Remote Similarity	NPC478013
0.6975	Remote Similarity	NPC477516
0.6974	Remote Similarity	NPC471194
0.6974	Remote Similarity	NPC471193
0.6974	Remote Similarity	NPC153980
0.6974	Remote Similarity	NPC6865
0.697	Remote Similarity	NPC473310
0.6963	Remote Similarity	NPC133003
0.6962	Remote Similarity	NPC326363
0.6951	Remote Similarity	NPC476874
0.6948	Remote Similarity	NPC470205
0.6938	Remote Similarity	NPC242269
0.693	Remote Similarity	NPC72956
0.6927	Remote Similarity	NPC194881
0.6926	Remote Similarity	NPC79386
0.6919	Remote Similarity	NPC64436
0.6919	Remote Similarity	NPC248454
0.6916	Remote Similarity	NPC477003
0.6897	Remote Similarity	NPC475736
0.6894	Remote Similarity	NPC477633
0.6892	Remote Similarity	NPC475914
0.6892	Remote Similarity	NPC220797
0.6892	Remote Similarity	NPC474318
0.6892	Remote Similarity	NPC201266
0.6892	Remote Similarity	NPC268744
0.6892	Remote Similarity	NPC153123
0.6889	Remote Similarity	NPC314930
0.6889	Remote Similarity	NPC214827
0.6887	Remote Similarity	NPC248462
0.6881	Remote Similarity	NPC200214
0.6878	Remote Similarity	NPC475258
0.6873	Remote Similarity	NPC321939
0.6866	Remote Similarity	NPC175474
0.6861	Remote Similarity	NPC77241
0.6861	Remote Similarity	NPC470497
0.6861	Remote Similarity	NPC269203
0.6861	Remote Similarity	NPC13456
0.6861	Remote Similarity	NPC166209
0.6854	Remote Similarity	NPC15840
0.6852	Remote Similarity	NPC478077
0.6847	Remote Similarity	NPC476219
0.684	Remote Similarity	NPC314882
0.6836	Remote Similarity	NPC315467
0.6835	Remote Similarity	NPC24370
0.6835	Remote Similarity	NPC319232
0.683	Remote Similarity	NPC300183
0.6829	Remote Similarity	NPC276085
0.6818	Remote Similarity	NPC326422
0.6816	Remote Similarity	NPC313421
0.6814	Remote Similarity	NPC470489
0.6814	Remote Similarity	NPC88115
0.6812	Remote Similarity	NPC21174
0.6812	Remote Similarity	NPC271797
0.6808	Remote Similarity	NPC126709
0.6808	Remote Similarity	NPC248041
0.6808	Remote Similarity	NPC283219
0.6802	Remote Similarity	NPC227582
0.68	Remote Similarity	NPC193761
0.6798	Remote Similarity	NPC475024
0.6798	Remote Similarity	NPC478006
0.6793	Remote Similarity	NPC474196
0.6789	Remote Similarity	NPC477109
0.6789	Remote Similarity	NPC477108
0.6789	Remote Similarity	NPC477107
0.6787	Remote Similarity	NPC477635
0.6787	Remote Similarity	NPC477630
0.6786	Remote Similarity	NPC252338
0.6783	Remote Similarity	NPC54981
0.6778	Remote Similarity	NPC33949
0.6773	Remote Similarity	NPC47190
0.6771	Remote Similarity	NPC131887
0.6771	Remote Similarity	NPC52557
0.6766	Remote Similarity	NPC474195
0.6765	Remote Similarity	NPC475338
0.6765	Remote Similarity	NPC909
0.6763	Remote Similarity	NPC63031
0.6761	Remote Similarity	NPC145885
0.6761	Remote Similarity	NPC157583
0.6761	Remote Similarity	NPC14113
0.6761	Remote Similarity	NPC84827

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 NPC19170 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	207
0.1-0.2	572
0.2-0.3	1139
0.3-0.4	2143
0.4-0.5	2152
0.5-0.6	2187
0.6-0.7	700
0.7-0.8	50
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
0.7752	Intermediate Similarity	NPD7594	Clinical (unspecified phase)
0.7751	Intermediate Similarity	NPD7619	Phase 3
0.7751	Intermediate Similarity	NPD7618	Phase 3
0.7617	Intermediate Similarity	NPD7903	Clinical (unspecified phase)
0.7604	Intermediate Similarity	NPD8493	Clinical (unspecified phase)
0.7602	Intermediate Similarity	NPD7971	Clinical (unspecified phase)
0.7602	Intermediate Similarity	NPD7970	Approved
0.7593	Intermediate Similarity	NPD8272	Phase 2
0.75	Intermediate Similarity	NPD7809	Clinical (unspecified phase)
0.7489	Intermediate Similarity	NPD7661	Clinical (unspecified phase)
0.7457	Intermediate Similarity	NPD7791	Approved
0.7457	Intermediate Similarity	NPD7950	Approved
0.7457	Intermediate Similarity	NPD7951	Approved
0.7457	Intermediate Similarity	NPD7952	Approved
0.7457	Intermediate Similarity	NPD7953	Approved
0.7457	Intermediate Similarity	NPD7790	Approved
0.7457	Intermediate Similarity	NPD7789	Approved
0.7451	Intermediate Similarity	NPD6044	Discontinued
0.7435	Intermediate Similarity	NPD7780	Approved
0.7435	Intermediate Similarity	NPD7781	Approved
0.7432	Intermediate Similarity	NPD7195	Clinical (unspecified phase)
0.7418	Intermediate Similarity	NPD7944	Discontinued
0.7391	Intermediate Similarity	NPD7730	Approved
0.7391	Intermediate Similarity	NPD7731	Approved
0.7378	Intermediate Similarity	NPD8000	Clinical (unspecified phase)
0.7352	Intermediate Similarity	NPD8114	Approved
0.7352	Intermediate Similarity	NPD8115	Approved
0.7339	Intermediate Similarity	NPD6268	Phase 1
0.7339	Intermediate Similarity	NPD6269	Clinical (unspecified phase)
0.7328	Intermediate Similarity	NPD7824	Approved
0.7304	Intermediate Similarity	NPD7271	Approved
0.7285	Intermediate Similarity	NPD6838	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD8169	Discontinued
0.7273	Intermediate Similarity	NPD7711	Discontinued
0.7252	Intermediate Similarity	NPD7666	Phase 3
0.7252	Intermediate Similarity	NPD7665	Phase 2
0.7232	Intermediate Similarity	NPD8013	Clinical (unspecified phase)
0.7215	Intermediate Similarity	NPD7817	Phase 1
0.7202	Intermediate Similarity	NPD7621	Clinical (unspecified phase)
0.7198	Intermediate Similarity	NPD8289	Discontinued
0.7195	Intermediate Similarity	NPD7712	Clinical (unspecified phase)
0.7189	Intermediate Similarity	NPD6664	Approved
0.717	Intermediate Similarity	NPD5820	Clinical (unspecified phase)
0.7156	Intermediate Similarity	NPD7564	Discontinued
0.7156	Intermediate Similarity	NPD7470	Discontinued
0.7136	Intermediate Similarity	NPD3486	Clinical (unspecified phase)
0.713	Intermediate Similarity	NPD8322	Phase 2
0.711	Intermediate Similarity	NPD2880	Discontinued
0.7103	Intermediate Similarity	NPD8110	Clinical (unspecified phase)
0.7098	Intermediate Similarity	NPD2442	Approved
0.7098	Intermediate Similarity	NPD2443	Approved
0.7087	Intermediate Similarity	NPD5199	Approved
0.7087	Intermediate Similarity	NPD5198	Approved
0.7072	Intermediate Similarity	NPD8072	Approved
0.7064	Intermediate Similarity	NPD7023	Clinical (unspecified phase)
0.7056	Intermediate Similarity	NPD3961	Discontinued
0.704	Intermediate Similarity	NPD5426	Phase 3
0.7035	Intermediate Similarity	NPD7998	Clinical (unspecified phase)
0.7028	Intermediate Similarity	NPD5728	Clinical (unspecified phase)
0.7021	Intermediate Similarity	NPD6164	Phase 2
0.7021	Intermediate Similarity	NPD6165	Phase 2
0.7018	Intermediate Similarity	NPD8094	Discontinued
0.701	Intermediate Similarity	NPD6771	Discontinued
0.7009	Intermediate Similarity	NPD7026	Phase 2
0.7005	Intermediate Similarity	NPD4615	Phase 2
0.7	Intermediate Similarity	NPD8256	Approved
0.7	Intermediate Similarity	NPD8258	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD8257	Approved
0.6982	Remote Similarity	NPD7727	Phase 2
0.6982	Remote Similarity	NPD5017	Discontinued
0.698	Remote Similarity	NPD8250	Phase 2
0.6978	Remote Similarity	NPD6328	Clinical (unspecified phase)
0.6974	Remote Similarity	NPD8093	Discontinued
0.697	Remote Similarity	NPD6470	Phase 3
0.6968	Remote Similarity	NPD7000	Clinical (unspecified phase)
0.6968	Remote Similarity	NPD6999	Discontinued
0.6961	Remote Similarity	NPD6454	Clinical (unspecified phase)
0.6959	Remote Similarity	NPD6180	Clinical (unspecified phase)
0.6951	Remote Similarity	NPD8073	Approved
0.6946	Remote Similarity	NPD8047	Clinical (unspecified phase)
0.6934	Remote Similarity	NPD6595	Phase 3
0.6933	Remote Similarity	NPD5489	Phase 1
0.6933	Remote Similarity	NPD7001	Phase 3
0.6933	Remote Similarity	NPD5491	Phase 3
0.6926	Remote Similarity	NPD2787	Clinical (unspecified phase)
0.6926	Remote Similarity	NPD8406	Clinical (unspecified phase)
0.6926	Remote Similarity	NPD7823	Clinical (unspecified phase)
0.692	Remote Similarity	NPD8484	Phase 2
0.6916	Remote Similarity	NPD2408	Discontinued
0.6916	Remote Similarity	NPD7482	Phase 2
0.6916	Remote Similarity	NPD7483	Phase 2
0.6916	Remote Similarity	NPD7704	Clinical (unspecified phase)
0.6909	Remote Similarity	NPD7818	Clinical (unspecified phase)
0.6909	Remote Similarity	NPD7027	Phase 3
0.6907	Remote Similarity	NPD7603	Discontinued
0.6903	Remote Similarity	NPD5864	Phase 2
0.69	Remote Similarity	NPD8458	Clinical (unspecified phase)
0.6897	Remote Similarity	NPD8405	Clinical (unspecified phase)
0.6894	Remote Similarity	NPD6173	Approved
0.6892	Remote Similarity	NPD6137	Clinical (unspecified phase)
0.6892	Remote Similarity	NPD7049	Clinical (unspecified phase)
0.6892	Remote Similarity	NPD2405	Phase 3
0.6888	Remote Similarity	NPD6986	Phase 1
0.6875	Remote Similarity	NPD3015	Discontinued
0.687	Remote Similarity	NPD8488	Clinical (unspecified phase)
0.6864	Remote Similarity	NPD5987	Approved
0.6864	Remote Similarity	NPD5986	Approved
0.6858	Remote Similarity	NPD2849	Clinical (unspecified phase)
0.6857	Remote Similarity	NPD750	Phase 2
0.6856	Remote Similarity	NPD4614	Clinical (unspecified phase)
0.6854	Remote Similarity	NPD6277	Clinical (unspecified phase)
0.6852	Remote Similarity	NPD4426	Clinical (unspecified phase)
0.6844	Remote Similarity	NPD5487	Phase 1
0.6838	Remote Similarity	NPD5884	Clinical (unspecified phase)
0.6838	Remote Similarity	NPD6210	Phase 3
0.6824	Remote Similarity	NPD6578	Clinical (unspecified phase)
0.682	Remote Similarity	NPD5590	Clinical (unspecified phase)
0.682	Remote Similarity	NPD7394	Phase 2
0.6818	Remote Similarity	NPD5274	Clinical (unspecified phase)
0.6812	Remote Similarity	NPD3583	Phase 2
0.6812	Remote Similarity	NPD4051	Discontinued
0.6812	Remote Similarity	NPD7825	Clinical (unspecified phase)
0.681	Remote Similarity	NPD7543	Phase 2
0.6809	Remote Similarity	NPD6615	Clinical (unspecified phase)
0.6806	Remote Similarity	NPD6610	Clinical (unspecified phase)
0.6798	Remote Similarity	NPD4959	Approved
0.6798	Remote Similarity	NPD6521	Phase 3
0.6798	Remote Similarity	NPD6520	Phase 3
0.6798	Remote Similarity	NPD4960	Approved
0.6797	Remote Similarity	NPD7557	Clinical (unspecified phase)
0.6794	Remote Similarity	NPD5069	Clinical (unspecified phase)
0.6792	Remote Similarity	NPD749	Clinical (unspecified phase)
0.6789	Remote Similarity	NPD2850	Phase 1
0.6789	Remote Similarity	NPD2851	Clinical (unspecified phase)
0.6787	Remote Similarity	NPD7024	Clinical (unspecified phase)
0.6786	Remote Similarity	NPD8248	Clinical (unspecified phase)
0.6784	Remote Similarity	NPD6732	Clinical (unspecified phase)
0.6778	Remote Similarity	NPD7888	Approved
0.6778	Remote Similarity	NPD7887	Approved
0.6774	Remote Similarity	NPD5809	Phase 3
0.6771	Remote Similarity	NPD7204	Clinical (unspecified phase)
0.6771	Remote Similarity	NPD4364	Phase 1
0.6767	Remote Similarity	NPD8112	Clinical (unspecified phase)
0.6761	Remote Similarity	NPD3506	Approved
0.6761	Remote Similarity	NPD3505	Approved
0.6761	Remote Similarity	NPD6203	Clinical (unspecified phase)
0.6759	Remote Similarity	NPD2091	Phase 2
0.6759	Remote Similarity	NPD6178	Phase 3
0.6759	Remote Similarity	NPD2096	Phase 2
0.6754	Remote Similarity	NPD4415	Approved
0.6751	Remote Similarity	NPD7717	Approved
0.6751	Remote Similarity	NPD7716	Approved
0.6741	Remote Similarity	NPD6248	Phase 2
0.6741	Remote Similarity	NPD6249	Phase 2
0.674	Remote Similarity	NPD7208	Approved
0.674	Remote Similarity	NPD7209	Approved
0.674	Remote Similarity	NPD7207	Approved
0.674	Remote Similarity	NPD6288	Clinical (unspecified phase)
0.6729	Remote Similarity	NPD4079	Approved
0.6729	Remote Similarity	NPD4076	Approved
0.6727	Remote Similarity	NPD8240	Discontinued
0.6726	Remote Similarity	NPD3830	Phase 1
0.6726	Remote Similarity	NPD5446	Phase 2
0.6722	Remote Similarity	NPD8372	Clinical (unspecified phase)
0.6722	Remote Similarity	NPD8316	Phase 2
0.6722	Remote Similarity	NPD8317	Phase 2
0.6719	Remote Similarity	NPD5461	Discontinued
0.6715	Remote Similarity	NPD2511	Approved
0.6714	Remote Similarity	NPD4075	Phase 2
0.6714	Remote Similarity	NPD5021	Discontinued
0.6714	Remote Similarity	NPD4779	Clinical (unspecified phase)
0.6713	Remote Similarity	NPD2095	Phase 2
0.6713	Remote Similarity	NPD2092	Phase 2
0.6713	Remote Similarity	NPD2094	Phase 2
0.6712	Remote Similarity	NPD7175	Phase 1
0.6711	Remote Similarity	NPD7958	Clinical (unspecified phase)
0.6711	Remote Similarity	NPD4600	Approved
0.6711	Remote Similarity	NPD4601	Approved
0.6711	Remote Similarity	NPD7957	Phase 1
0.6711	Remote Similarity	NPD2008	Discontinued
0.6711	Remote Similarity	NPD7289	Clinical (unspecified phase)
0.6699	Remote Similarity	NPD2719	Clinical (unspecified phase)
0.6699	Remote Similarity	NPD2720	Phase 1
0.6697	Remote Similarity	NPD4922	Phase 2
0.6697	Remote Similarity	NPD3431	Approved
0.6697	Remote Similarity	NPD6665	Discontinued
0.6697	Remote Similarity	NPD3430	Approved
0.6681	Remote Similarity	NPD2411	Approved
0.6681	Remote Similarity	NPD3905	Phase 3
0.6681	Remote Similarity	NPD1506	Discontinued
0.6667	Remote Similarity	NPD482	Approved
0.6667	Remote Similarity	NPD2717	Phase 2
0.6667	Remote Similarity	NPD5322	Clinical (unspecified phase)
0.6653	Remote Similarity	NPD5935	Discontinued
0.6652	Remote Similarity	NPD6224	Clinical (unspecified phase)
0.6652	Remote Similarity	NPD7434	Approved
0.6651	Remote Similarity	NPD3610	Approved
0.6651	Remote Similarity	NPD3609	Approved
0.6651	Remote Similarity	NPD5555	Phase 1
0.665	Remote Similarity	NPD4637	Clinical (unspecified phase)

Bioactivity similarity: Similar Natural Products in NPASS

Bioactivity similarity was calculated based on bioactivity descriptors of compounds. The bioactivity descriptors were calculated by a recently developed AI algorithm Chemical Checker (CC) [Nature Biotechnology, 38:1087–1096, 2020; Nature Communications, 12:3932, 2021], which evaluated bioactivity similarities at five levels:
☉ A: chemistry similarity;
☉ B: biological targets similarity;
☉ C: networks similarity;
☉ D: cell-based bioactivity similarity;
☉ E: similarity based on clinical data.

Those 5 categories of CC bioactivity descriptors were calculated and then subjected to manifold projection using UMAP algorithm, to project all NPs on a 2-Dimensional space. The current NP was highlighted with a small circle in the 2-D map. Below figures: left-to-right, A-to-E.

A: chemistry similarity

B: biological targets similarity

C: networks similarity

D: cell-based bioactivity similarity

E: similarity based on clinical data