NPASS Compound

Structure

CID200672 OpenBabel06191715592D 33 36 0 0 1 0 0 0 0 0999 V2000 -4.6431 -2.1197 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.4685 -0.6900 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9922 -1.1788 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2068 3.1376 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2236 3.0235 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1054 1.7699 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8176 -0.6900 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3307 -1.1849 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3307 0.7459 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4946 1.2285 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0360 -0.4814 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.6431 -1.1666 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1667 -0.7022 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1054 2.7849 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5462 2.3357 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1667 0.2632 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.4946 -0.7022 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.8176 0.2632 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6202 -0.2194 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.2013 0.6504 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.2015 -1.0893 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.2601 0.8651 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.4946 0.2632 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.3989 -0.2719 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.8602 3.3868 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.6118 2.5785 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.6431 0.7397 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5458 -0.2193 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.2493 1.8304 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 1.8031 1.4052 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.9922 0.7397 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.2603 -1.3040 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 4 14 1 0 0 0 0 5 15 1 0 0 0 0 6 22 1 0 0 0 0 7 12 1 0 0 0 0 7 18 1 0 0 0 0 8 13 2 0 0 0 0 8 17 1 0 0 0 0 9 16 1 0 0 0 0 9 23 1 0 0 0 0 10 29 1 0 0 0 0 11 24 1 0 0 0 0 11 30 1 0 0 0 0 13 16 1 0 0 0 0 14 25 2 0 0 0 0 14 29 1 0 0 0 0 15 26 2 0 0 0 0 15 31 1 0 0 0 0 16 32 1 1 0 0 0 17 23 1 6 0 0 0 17 33 1 0 0 0 0 18 27 2 0 0 0 0 18 32 1 0 0 0 0 19 20 1 0 0 0 0 19 21 1 0 0 0 0 19 28 1 1 0 0 0 20 22 1 6 0 0 0 20 31 1 0 0 0 0 21 24 1 6 0 0 0 21 33 1 0 0 0 0 22 23 1 1 0 0 0 23 10 1 1 0 0 0 24 22 1 1 0 0 0 24 30 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	466.22
Volume:	458.0
LogP:	2.504
LogD:	1.779
LogS:	-4.444
# Rotatable Bonds:	9
TPSA:	120.89
# H-Bond Aceptor:	9
# H-Bond Donor:	1
# Rings:	4
# Heavy Atoms:	9

MedChem Properties

QED Drug-Likeness Score:	0.27
Synthetic Accessibility Score:	6.062
Fsp3:	0.792
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.288
MDCK Permeability:	6.206853140611202e-05
Pgp-inhibitor:	0.721
Pgp-substrate:	0.993
Human Intestinal Absorption (HIA):	0.05
20% Bioavailability (F20%):	0.183
30% Bioavailability (F30%):	0.911

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.427
Plasma Protein Binding (PPB):	38.368408203125%
Volume Distribution (VD):	1.066
Pgp-substrate:	36.86461639404297%

ADMET: Metabolism

CYP1A2-inhibitor:	0.023
CYP1A2-substrate:	0.078
CYP2C19-inhibitor:	0.033
CYP2C19-substrate:	0.518
CYP2C9-inhibitor:	0.058
CYP2C9-substrate:	0.023
CYP2D6-inhibitor:	0.018
CYP2D6-substrate:	0.068
CYP3A4-inhibitor:	0.478
CYP3A4-substrate:	0.371

ADMET: Excretion

Clearance (CL):	3.222
Half-life (T1/2):	0.644

ADMET: Toxicity

hERG Blockers:	0.038
Human Hepatotoxicity (H-HT):	0.687
Drug-inuced Liver Injury (DILI):	0.903
AMES Toxicity:	0.939
Rat Oral Acute Toxicity:	0.295
Maximum Recommended Daily Dose:	0.139
Skin Sensitization:	0.428
Carcinogencity:	0.101
Eye Corrosion:	0.004
Eye Irritation:	0.039
Respiratory Toxicity:	0.234

Download Data

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

Natural Product: NPC200672

Natural Product ID:	NPC200672
*Common Name:**	T-2 Toxin
IUPAC Name:	n.a.
Synonyms:	T2 toxin
Standard InCHIKey:	BXFOFFBJRFZBQZ-QYWOHJEZSA-N
Standard InCHI:	InChI=1S/C24H34O9/c1-12(2)7-18(27)32-16-9-23(10-29-14(4)25)17(8-13(16)3)33-21-19(28)20(31-15(5)26)22(23,6)24(21)11-30-24/h8,12,16-17,19-21,28H,7,9-11H2,1-6H3/t16-,17+,19+,20+,21+,22+,23+,24-/m0/s1
SMILES:	CC(CC(=O)O[C@H]1C[C@@]2(COC(=O)C)[C@@H](C=C1C)O[C@H]1[C@]3([C@]2(C)[C@H](OC(=O)C)[C@H]1O)CO3)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL152423
PubChem CID:	5284461
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001550] Sesquiterpenoids [CHEMONTID:0001789] Trichothecenes

*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
NPO11220	Fusarium sporotrichioides	Species	Nectriaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[1800633]
NPO25042	Fusarium tricinctum	Species	Nectriaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21090694]
NPO25042	Fusarium tricinctum	Species	Nectriaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24175613]
NPO11220	Fusarium sporotrichioides	Species	Nectriaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25475336]
NPO40950	Verrucarol diacetoxyscirpenol	Species	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[6481362]
NPO15511	Fusarium heterosporum	Species	Nectriaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[7264681]
NPO11220	Fusarium sporotrichioides	Species	Nectriaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[8289061]
NPO25042	Fusarium tricinctum	Species	Nectriaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO15511	Fusarium heterosporum	Species	Nectriaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25042	Fusarium tricinctum	Species	Nectriaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11220	Fusarium sporotrichioides	Species	Nectriaceae	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
EC50	1
ED50	1
LD50	4
Others	7

Activity Type	# Activity
Cell Line	2
Organism	10
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1864	Cell Line	L5178Y	Mus musculus	LC50	=	0.0018	ug.mL-1	PMID[565717]
NPT111	Cell Line	K562	Homo sapiens	EC50	=	2.1	nM	PMID[565719]
NPT27	Others	Unspecified		LC100	=	5.0	ng/ml	PMID[565718]
NPT32	Organism	Mus musculus	Mus musculus	LD50	=	5.2	mg.kg-1	PMID[565719]
NPT32	Organism	Mus musculus	Mus musculus	Activity	=	3.0	n.a.	PMID[565719]
NPT673	Organism	Gallus gallus	Gallus gallus	LD50	=	1.75	mg.kg-1	PMID[565720]
NPT419	Organism	Oryctolagus cuniculus	Oryctolagus cuniculus	ED50	<	0.16	ug	PMID[565720]
NPT32	Organism	Mus musculus	Mus musculus	LD50	>=	3.29	mg.kg-1	PMID[565721]
NPT32	Organism	Mus musculus	Mus musculus	Activity	=	0.005	ug ml-1	PMID[565721]
NPT32	Organism	Mus musculus	Mus musculus	MED	=	50.2	ng	PMID[565721]
NPT312	Organism	Saccharomyces cerevisiae	Saccharomyces cerevisiae	Ratio	=	2400.0	n.a.	PMID[565722]
NPT312	Organism	Saccharomyces cerevisiae	Saccharomyces cerevisiae	Activity	=	2400.0	n.a.	PMID[565722]
NPT1339	Organism	Arabidopsis thaliana	Arabidopsis thaliana	LD50	=	0.5	uM	PMID[565723]

☑ 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 NPC200672 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	192
0.1-0.2	1194
0.2-0.3	4695
0.3-0.4	12516
0.4-0.5	9762
0.5-0.6	6826
0.6-0.7	6274
0.7-0.8	1158
0.8-0.85	23
0.85-0.9	30
0.9-0.95	12
0.95-1	15

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC214714
0.9894	High Similarity	NPC26557
0.9789	High Similarity	NPC475956
0.9789	High Similarity	NPC252242
0.9688	High Similarity	NPC474783
0.9688	High Similarity	NPC232515
0.9688	High Similarity	NPC260809
0.9681	High Similarity	NPC79449
0.9681	High Similarity	NPC474957
0.9583	High Similarity	NPC475986
0.9574	High Similarity	NPC476057
0.9574	High Similarity	NPC347923
0.9474	High Similarity	NPC274458
0.9368	High Similarity	NPC182811
0.9362	High Similarity	NPC240838
0.898	High Similarity	NPC79631
0.8952	High Similarity	NPC305044
0.8952	High Similarity	NPC265290
0.8942	High Similarity	NPC313921
0.8942	High Similarity	NPC98038
0.8911	High Similarity	NPC29389
0.8911	High Similarity	NPC93026
0.8911	High Similarity	NPC469960
0.8911	High Similarity	NPC265502
0.8857	High Similarity	NPC101965
0.8857	High Similarity	NPC101400
0.8824	High Similarity	NPC469959
0.8824	High Similarity	NPC469957
0.8824	High Similarity	NPC472263
0.8824	High Similarity	NPC108682
0.875	High Similarity	NPC50223
0.8737	High Similarity	NPC197107
0.8571	High Similarity	NPC41551
0.8416	Intermediate Similarity	NPC98813
0.8416	Intermediate Similarity	NPC13743
0.8365	Intermediate Similarity	NPC475290
0.8365	Intermediate Similarity	NPC470980
0.8364	Intermediate Similarity	NPC474286
0.8364	Intermediate Similarity	NPC475130
0.8333	Intermediate Similarity	NPC287075
0.8317	Intermediate Similarity	NPC65700
0.8269	Intermediate Similarity	NPC475585
0.8269	Intermediate Similarity	NPC473577
0.8269	Intermediate Similarity	NPC474550
0.8173	Intermediate Similarity	NPC123505
0.8148	Intermediate Similarity	NPC71680
0.81	Intermediate Similarity	NPC281775
0.8095	Intermediate Similarity	NPC121518
0.8095	Intermediate Similarity	NPC169843
0.8095	Intermediate Similarity	NPC201144
0.8095	Intermediate Similarity	NPC80809
0.8095	Intermediate Similarity	NPC103298
0.8095	Intermediate Similarity	NPC475331
0.8095	Intermediate Similarity	NPC181104
0.8095	Intermediate Similarity	NPC288502
0.8095	Intermediate Similarity	NPC475335
0.8077	Intermediate Similarity	NPC470972
0.8073	Intermediate Similarity	NPC126691
0.8073	Intermediate Similarity	NPC241477
0.8056	Intermediate Similarity	NPC15551
0.8019	Intermediate Similarity	NPC60315
0.8	Intermediate Similarity	NPC475623
0.8	Intermediate Similarity	NPC473694
0.8	Intermediate Similarity	NPC474124
0.8	Intermediate Similarity	NPC475334
0.8	Intermediate Similarity	NPC473523
0.7981	Intermediate Similarity	NPC475617
0.7963	Intermediate Similarity	NPC77089
0.7961	Intermediate Similarity	NPC222303
0.7941	Intermediate Similarity	NPC113433
0.7938	Intermediate Similarity	NPC137253
0.7938	Intermediate Similarity	NPC477668
0.7928	Intermediate Similarity	NPC216665
0.7925	Intermediate Similarity	NPC473543
0.7905	Intermediate Similarity	NPC475344
0.7905	Intermediate Similarity	NPC476471
0.7905	Intermediate Similarity	NPC472552
0.7895	Intermediate Similarity	NPC79579
0.789	Intermediate Similarity	NPC472214
0.789	Intermediate Similarity	NPC472215
0.7885	Intermediate Similarity	NPC230546
0.787	Intermediate Similarity	NPC88701
0.7864	Intermediate Similarity	NPC210337
0.783	Intermediate Similarity	NPC474775
0.7812	Intermediate Similarity	NPC231601
0.781	Intermediate Similarity	NPC280991
0.781	Intermediate Similarity	NPC11974
0.781	Intermediate Similarity	NPC472554
0.7807	Intermediate Similarity	NPC278681
0.7807	Intermediate Similarity	NPC5292
0.7798	Intermediate Similarity	NPC284828
0.7798	Intermediate Similarity	NPC173905
0.7798	Intermediate Similarity	NPC472216
0.7798	Intermediate Similarity	NPC5475
0.7788	Intermediate Similarity	NPC203862
0.7788	Intermediate Similarity	NPC290693
0.7778	Intermediate Similarity	NPC72813
0.7778	Intermediate Similarity	NPC324327
0.7778	Intermediate Similarity	NPC475781
0.7778	Intermediate Similarity	NPC326994
0.7778	Intermediate Similarity	NPC194620
0.7778	Intermediate Similarity	NPC474421
0.7768	Intermediate Similarity	NPC43213
0.7768	Intermediate Similarity	NPC178289
0.7768	Intermediate Similarity	NPC106446
0.7767	Intermediate Similarity	NPC57664
0.7767	Intermediate Similarity	NPC88009
0.7759	Intermediate Similarity	NPC115349
0.7745	Intermediate Similarity	NPC472467
0.7739	Intermediate Similarity	NPC112936
0.7736	Intermediate Similarity	NPC109195
0.7736	Intermediate Similarity	NPC475038
0.7723	Intermediate Similarity	NPC235051
0.7719	Intermediate Similarity	NPC153440
0.7719	Intermediate Similarity	NPC16701
0.7719	Intermediate Similarity	NPC475401
0.7714	Intermediate Similarity	NPC473510
0.7714	Intermediate Similarity	NPC79303
0.7714	Intermediate Similarity	NPC130792
0.7714	Intermediate Similarity	NPC167974
0.7714	Intermediate Similarity	NPC272223
0.7706	Intermediate Similarity	NPC474664
0.7706	Intermediate Similarity	NPC128795
0.7706	Intermediate Similarity	NPC48548
0.7706	Intermediate Similarity	NPC55972
0.7706	Intermediate Similarity	NPC327286
0.7706	Intermediate Similarity	NPC217921
0.7706	Intermediate Similarity	NPC135015
0.7706	Intermediate Similarity	NPC233379
0.7706	Intermediate Similarity	NPC169888
0.7706	Intermediate Similarity	NPC14862
0.77	Intermediate Similarity	NPC299527
0.7699	Intermediate Similarity	NPC193382
0.7699	Intermediate Similarity	NPC310341
0.7699	Intermediate Similarity	NPC99620
0.7699	Intermediate Similarity	NPC199428
0.7699	Intermediate Similarity	NPC5311
0.7692	Intermediate Similarity	NPC239547
0.7692	Intermediate Similarity	NPC205143
0.7692	Intermediate Similarity	NPC475033
0.7692	Intermediate Similarity	NPC309503
0.7692	Intermediate Similarity	NPC155319
0.7692	Intermediate Similarity	NPC475032
0.7692	Intermediate Similarity	NPC473244
0.7692	Intermediate Similarity	NPC96597
0.7692	Intermediate Similarity	NPC125551
0.7692	Intermediate Similarity	NPC86843
0.7692	Intermediate Similarity	NPC91197
0.7685	Intermediate Similarity	NPC220217
0.7685	Intermediate Similarity	NPC119855
0.7685	Intermediate Similarity	NPC9303
0.7685	Intermediate Similarity	NPC186668
0.7685	Intermediate Similarity	NPC16313
0.7672	Intermediate Similarity	NPC312481
0.767	Intermediate Similarity	NPC93869
0.767	Intermediate Similarity	NPC6765
0.7664	Intermediate Similarity	NPC472821
0.7664	Intermediate Similarity	NPC329834
0.7664	Intermediate Similarity	NPC69171
0.7664	Intermediate Similarity	NPC474165
0.7664	Intermediate Similarity	NPC4620
0.766	Intermediate Similarity	NPC477089
0.7658	Intermediate Similarity	NPC470076
0.7658	Intermediate Similarity	NPC474750
0.7652	Intermediate Similarity	NPC29639
0.7652	Intermediate Similarity	NPC477092
0.7652	Intermediate Similarity	NPC81222
0.7652	Intermediate Similarity	NPC270850
0.7652	Intermediate Similarity	NPC44899
0.7652	Intermediate Similarity	NPC5883
0.7652	Intermediate Similarity	NPC304260
0.7652	Intermediate Similarity	NPC305260
0.7652	Intermediate Similarity	NPC213761
0.7652	Intermediate Similarity	NPC291820
0.7652	Intermediate Similarity	NPC35171
0.7647	Intermediate Similarity	NPC470187
0.7636	Intermediate Similarity	NPC475922
0.7636	Intermediate Similarity	NPC40728
0.7636	Intermediate Similarity	NPC316974
0.7636	Intermediate Similarity	NPC128133
0.7636	Intermediate Similarity	NPC15218
0.7632	Intermediate Similarity	NPC185287
0.7632	Intermediate Similarity	NPC471355
0.7632	Intermediate Similarity	NPC99728
0.7632	Intermediate Similarity	NPC50305
0.7632	Intermediate Similarity	NPC471353
0.7632	Intermediate Similarity	NPC87250
0.7632	Intermediate Similarity	NPC158344
0.7632	Intermediate Similarity	NPC471351
0.7632	Intermediate Similarity	NPC93883
0.7632	Intermediate Similarity	NPC27507
0.7632	Intermediate Similarity	NPC157380
0.7632	Intermediate Similarity	NPC471354
0.7632	Intermediate Similarity	NPC473852
0.7632	Intermediate Similarity	NPC474418
0.7632	Intermediate Similarity	NPC142066
0.7632	Intermediate Similarity	NPC152615
0.7632	Intermediate Similarity	NPC157376
0.7632	Intermediate Similarity	NPC243196
0.7632	Intermediate Similarity	NPC77319

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 NPC200672 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	152
0.1-0.2	1527
0.2-0.3	4026
0.3-0.4	2389
0.4-0.5	588
0.5-0.6	261
0.6-0.7	197
0.7-0.8	10
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
0.78	Intermediate Similarity	NPD6698	Approved
0.78	Intermediate Similarity	NPD46	Approved
0.7619	Intermediate Similarity	NPD7638	Approved
0.7565	Intermediate Similarity	NPD7328	Approved
0.7565	Intermediate Similarity	NPD7327	Approved
0.7547	Intermediate Similarity	NPD7640	Approved
0.7547	Intermediate Similarity	NPD7639	Approved
0.7521	Intermediate Similarity	NPD7503	Approved
0.7521	Intermediate Similarity	NPD8033	Approved
0.75	Intermediate Similarity	NPD7516	Approved
0.7451	Intermediate Similarity	NPD7838	Discovery
0.7436	Intermediate Similarity	NPD8377	Approved
0.7436	Intermediate Similarity	NPD8294	Approved
0.7417	Intermediate Similarity	NPD7507	Approved
0.7387	Intermediate Similarity	NPD6686	Approved
0.7373	Intermediate Similarity	NPD8378	Approved
0.7373	Intermediate Similarity	NPD8380	Approved
0.7373	Intermediate Similarity	NPD8335	Approved
0.7373	Intermediate Similarity	NPD8379	Approved
0.7373	Intermediate Similarity	NPD8296	Approved
0.7321	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.7297	Intermediate Similarity	NPD6412	Phase 2
0.7281	Intermediate Similarity	NPD6053	Discontinued
0.7257	Intermediate Similarity	NPD6371	Approved
0.7236	Intermediate Similarity	NPD7319	Approved
0.7179	Intermediate Similarity	NPD7115	Discovery
0.7157	Intermediate Similarity	NPD4250	Approved
0.7157	Intermediate Similarity	NPD4251	Approved
0.7156	Intermediate Similarity	NPD5344	Discontinued
0.7143	Intermediate Similarity	NPD4820	Approved
0.7143	Intermediate Similarity	NPD5790	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD4822	Approved
0.7143	Intermediate Similarity	NPD4819	Approved
0.7143	Intermediate Similarity	NPD7899	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD6319	Approved
0.7143	Intermediate Similarity	NPD4821	Approved
0.7129	Intermediate Similarity	NPD6082	Clinical (unspecified phase)
0.7105	Intermediate Similarity	NPD5955	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD4249	Approved
0.7019	Intermediate Similarity	NPD6051	Approved
0.6983	Remote Similarity	NPD8297	Approved
0.6972	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6972	Remote Similarity	NPD4225	Approved
0.6939	Remote Similarity	NPD4271	Approved
0.6939	Remote Similarity	NPD4268	Approved
0.6937	Remote Similarity	NPD7632	Discontinued
0.6923	Remote Similarity	NPD4632	Approved
0.6923	Remote Similarity	NPD8133	Approved
0.6903	Remote Similarity	NPD7128	Approved
0.6903	Remote Similarity	NPD5739	Approved
0.6903	Remote Similarity	NPD6675	Approved
0.6903	Remote Similarity	NPD6402	Approved
0.6897	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6887	Remote Similarity	NPD7637	Suspended
0.6881	Remote Similarity	NPD6083	Phase 2
0.6881	Remote Similarity	NPD6084	Phase 2
0.687	Remote Similarity	NPD6373	Approved
0.687	Remote Similarity	NPD6372	Approved
0.6842	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6832	Remote Similarity	NPD6435	Approved
0.6827	Remote Similarity	NPD7524	Approved
0.6803	Remote Similarity	NPD8513	Phase 3
0.6803	Remote Similarity	NPD8515	Approved
0.6803	Remote Similarity	NPD8517	Approved
0.6803	Remote Similarity	NPD8516	Approved
0.6783	Remote Similarity	NPD6881	Approved
0.6783	Remote Similarity	NPD7320	Approved
0.6783	Remote Similarity	NPD6899	Approved
0.6774	Remote Similarity	NPD7492	Approved
0.6757	Remote Similarity	NPD6648	Approved
0.6754	Remote Similarity	NPD6008	Approved
0.6752	Remote Similarity	NPD6649	Approved
0.6752	Remote Similarity	NPD6650	Approved
0.6729	Remote Similarity	NPD7983	Approved
0.6721	Remote Similarity	NPD6059	Approved
0.6721	Remote Similarity	NPD6054	Approved
0.672	Remote Similarity	NPD6616	Approved
0.6699	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6697	Remote Similarity	NPD5695	Phase 3
0.6696	Remote Similarity	NPD5701	Approved
0.6696	Remote Similarity	NPD5697	Approved
0.6695	Remote Similarity	NPD6882	Approved
0.6694	Remote Similarity	NPD7604	Phase 2
0.6667	Remote Similarity	NPD7290	Approved
0.6667	Remote Similarity	NPD7102	Approved
0.6667	Remote Similarity	NPD6883	Approved
0.6667	Remote Similarity	NPD6399	Phase 3
0.6667	Remote Similarity	NPD8293	Discontinued
0.6667	Remote Similarity	NPD7078	Approved
0.6638	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6636	Remote Similarity	NPD5785	Approved
0.6634	Remote Similarity	NPD5368	Approved
0.6614	Remote Similarity	NPD7736	Approved
0.6613	Remote Similarity	NPD6370	Approved
0.6612	Remote Similarity	NPD6009	Approved
0.661	Remote Similarity	NPD6617	Approved
0.661	Remote Similarity	NPD8130	Phase 1
0.661	Remote Similarity	NPD6847	Approved
0.661	Remote Similarity	NPD6869	Approved
0.6602	Remote Similarity	NPD5362	Discontinued
0.6602	Remote Similarity	NPD7154	Phase 3
0.6602	Remote Similarity	NPD6695	Phase 3
0.6581	Remote Similarity	NPD6013	Approved
0.6581	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6581	Remote Similarity	NPD6014	Approved
0.6581	Remote Similarity	NPD6012	Approved
0.6571	Remote Similarity	NPD6684	Approved
0.6571	Remote Similarity	NPD7334	Approved
0.6571	Remote Similarity	NPD6409	Approved
0.6571	Remote Similarity	NPD7146	Approved
0.6571	Remote Similarity	NPD5330	Approved
0.6571	Remote Similarity	NPD7521	Approved
0.6549	Remote Similarity	NPD4159	Approved
0.6542	Remote Similarity	NPD1695	Approved
0.6535	Remote Similarity	NPD8074	Phase 3
0.6532	Remote Similarity	NPD6016	Approved
0.6532	Remote Similarity	NPD6015	Approved
0.6532	Remote Similarity	NPD5983	Phase 2
0.6525	Remote Similarity	NPD4634	Approved
0.6518	Remote Similarity	NPD5696	Approved
0.6514	Remote Similarity	NPD5778	Approved
0.6514	Remote Similarity	NPD5779	Approved
0.6496	Remote Similarity	NPD6011	Approved
0.648	Remote Similarity	NPD5988	Approved
0.6471	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6462	Remote Similarity	NPD7260	Phase 2
0.6457	Remote Similarity	NPD6336	Discontinued
0.6449	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6449	Remote Similarity	NPD6903	Approved
0.6442	Remote Similarity	NPD5332	Approved
0.6442	Remote Similarity	NPD5331	Approved
0.6436	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6429	Remote Similarity	NPD4755	Approved
0.6422	Remote Similarity	NPD5693	Phase 1
0.6422	Remote Similarity	NPD6411	Approved
0.6408	Remote Similarity	NPD4790	Discontinued
0.6408	Remote Similarity	NPD5369	Approved
0.6396	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6389	Remote Similarity	NPD4753	Phase 2
0.6381	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6381	Remote Similarity	NPD3666	Approved
0.6381	Remote Similarity	NPD3133	Approved
0.6381	Remote Similarity	NPD3665	Phase 1
0.6364	Remote Similarity	NPD4202	Approved
0.6355	Remote Similarity	NPD7750	Discontinued
0.6355	Remote Similarity	NPD4751	Clinical (unspecified phase)
0.6348	Remote Similarity	NPD5211	Phase 2
0.6346	Remote Similarity	NPD4270	Approved
0.6346	Remote Similarity	NPD4269	Approved
0.6339	Remote Similarity	NPD4792	Clinical (unspecified phase)
0.6321	Remote Similarity	NPD1694	Approved
0.6321	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.6316	Remote Similarity	NPD5285	Approved
0.6316	Remote Similarity	NPD5286	Approved
0.6316	Remote Similarity	NPD4700	Approved
0.6316	Remote Similarity	NPD4696	Approved
0.6311	Remote Similarity	NPD6931	Approved
0.6311	Remote Similarity	NPD7525	Registered
0.6311	Remote Similarity	NPD6930	Phase 2
0.6299	Remote Similarity	NPD8328	Phase 3
0.6299	Remote Similarity	NPD6067	Discontinued
0.6273	Remote Similarity	NPD5281	Approved
0.6273	Remote Similarity	NPD5284	Approved
0.6271	Remote Similarity	NPD6685	Approved
0.6262	Remote Similarity	NPD5786	Approved
0.6262	Remote Similarity	NPD6098	Approved
0.626	Remote Similarity	NPD6274	Approved
0.624	Remote Similarity	NPD7101	Approved
0.624	Remote Similarity	NPD7100	Approved
0.6239	Remote Similarity	NPD6673	Approved
0.6239	Remote Similarity	NPD5141	Approved
0.6239	Remote Similarity	NPD6080	Approved
0.6239	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6239	Remote Similarity	NPD6904	Approved
0.6239	Remote Similarity	NPD6101	Approved
0.6238	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.6238	Remote Similarity	NPD6933	Approved
0.6231	Remote Similarity	NPD6033	Approved
0.6226	Remote Similarity	NPD4786	Approved
0.6214	Remote Similarity	NPD6929	Approved
0.621	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6207	Remote Similarity	NPD5226	Approved
0.6207	Remote Similarity	NPD4633	Approved
0.6207	Remote Similarity	NPD5225	Approved
0.6207	Remote Similarity	NPD5224	Approved
0.6202	Remote Similarity	NPD8273	Phase 1
0.619	Remote Similarity	NPD3667	Approved
0.619	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6186	Remote Similarity	NPD4767	Approved
0.6186	Remote Similarity	NPD4768	Approved
0.6168	Remote Similarity	NPD5363	Approved
0.6165	Remote Similarity	NPD6845	Suspended
0.6161	Remote Similarity	NPD5282	Discontinued
0.6161	Remote Similarity	NPD7748	Approved
0.616	Remote Similarity	NPD6335	Approved
0.6154	Remote Similarity	NPD4252	Approved
0.6154	Remote Similarity	NPD7514	Phase 3
0.6154	Remote Similarity	NPD5174	Approved
0.6154	Remote Similarity	NPD5175	Approved
0.6147	Remote Similarity	NPD6672	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