NPASS Compound

Structure

NPC161861 OpenBabel07101719242D 26 30 0 0 1 0 0 0 0 0999 V2000 -2.5981 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0844 2.3271 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.6722 1.5181 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2709 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0898 2.2226 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2654 0.6045 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 2.6831 1.3090 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 -0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6831 1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2709 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8660 -0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.0000 1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.7321 -0.0000 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 0.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6831 -0.3090 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 -0.0000 -0.0000 0.0000 N 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 0.8660 -1.5000 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 4 2 0 0 0 0 3 6 1 0 0 0 0 4 7 1 0 0 0 0 5 8 1 0 0 0 0 5 9 1 0 0 0 0 6 13 2 0 0 0 0 7 15 2 0 0 0 0 9 23 1 0 0 0 0 10 12 2 0 0 0 0 11 14 1 0 0 0 0 13 14 1 0 0 0 0 13 15 1 0 0 0 0 14 19 2 0 0 0 0 15 22 1 0 0 0 0 16 8 1 1 0 0 0 16 21 1 0 0 0 0 16 23 1 0 0 0 0 17 10 1 1 0 0 0 17 19 1 0 0 0 0 17 24 1 0 0 0 0 18 11 1 1 0 0 0 18 20 1 0 0 0 0 18 24 1 0 0 0 0 19 22 1 0 0 0 0 20 23 1 0 0 0 0 20 25 2 0 0 0 0 21 24 1 0 0 0 0 21 26 2 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	349.18
Volume:	361.105
LogP:	3.535
LogD:	3.044
LogS:	-3.534
# Rotatable Bonds:	1
TPSA:	56.41
# H-Bond Aceptor:	5
# H-Bond Donor:	1
# Rings:	5
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.805
Synthetic Accessibility Score:	3.751
Fsp3:	0.429
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.703
MDCK Permeability:	1.762174542818684e-05
Pgp-inhibitor:	0.032
Pgp-substrate:	0.363
Human Intestinal Absorption (HIA):	0.006
20% Bioavailability (F20%):	0.016
30% Bioavailability (F30%):	0.905

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.393
Plasma Protein Binding (PPB):	93.18448638916016%
Volume Distribution (VD):	0.81
Pgp-substrate:	5.528369903564453%

ADMET: Metabolism

CYP1A2-inhibitor:	0.063
CYP1A2-substrate:	0.245
CYP2C19-inhibitor:	0.892
CYP2C19-substrate:	0.324
CYP2C9-inhibitor:	0.736
CYP2C9-substrate:	0.888
CYP2D6-inhibitor:	0.021
CYP2D6-substrate:	0.182
CYP3A4-inhibitor:	0.744
CYP3A4-substrate:	0.85

ADMET: Excretion

Clearance (CL):	8.164
Half-life (T1/2):	0.178

ADMET: Toxicity

hERG Blockers:	0.022
Human Hepatotoxicity (H-HT):	0.957
Drug-inuced Liver Injury (DILI):	0.977
AMES Toxicity:	0.016
Rat Oral Acute Toxicity:	0.813
Maximum Recommended Daily Dose:	0.886
Skin Sensitization:	0.588
Carcinogencity:	0.566
Eye Corrosion:	0.003
Eye Irritation:	0.009
Respiratory Toxicity:	0.985

Download Data

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

Natural Product: NPC161861

Natural Product ID:	NPC161861
*Common Name:**	Demethoxyfumitremorgin C
IUPAC Name:	n.a.
Synonyms:	Demethoxyfumitremorgin C
Standard InCHIKey:	LQXCSIKDOISJTI-BZSNNMDCSA-N
Standard InCHI:	InChI=1S/C21H23N3O2/c1-12(2)10-17-19-14(13-6-3-4-7-15(13)22-19)11-18-20(25)23-9-5-8-16(23)21(26)24(17)18/h3-4,6-7,10,16-18,22H,5,8-9,11H2,1-2H3/t16-,17-,18-/m0/s1
SMILES:	CC(=C[C@@H]1N2C(=O)[C@@H]3CCCN3C(=O)[C@@H]2Cc2c1[nH]c1c2cccc1)C
Synthetic Gene Cluster:	BGC0000356;
ChEMBL Identifier:	CHEMBL39346
PubChem CID:	10337896
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000211] Indoles and derivatives [CHEMONTID:0001213] Pyridoindoles [CHEMONTID:0001914] Beta carbolines

*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
NPO10538	Aspergillus fumigatus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17616609]
NPO10538	Aspergillus fumigatus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17929896]
NPO10538	Aspergillus fumigatus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19113967]
NPO10538	Aspergillus fumigatus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19159274]
NPO10538	Aspergillus fumigatus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19256529]
NPO10538	Aspergillus fumigatus	Species	Aspergillaceae	Eukaryota	n.a.	isolated from sediment collected using a hand held deep water sampling device at >33 m depth in Vanuatu	2003	PMID[20303767]
NPO10538	Aspergillus fumigatus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21667925]
NPO10538	Aspergillus fumigatus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21954885]
NPO10538	Aspergillus fumigatus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22106303]
NPO10538	Aspergillus fumigatus	Species	Aspergillaceae	Eukaryota	stem bark of Melia azedarach	n.a.	n.a.	PMID[22409377]
NPO10538	Aspergillus fumigatus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23557488]
NPO10538	Aspergillus fumigatus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23563483]
NPO10538	Aspergillus fumigatus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[7622436]
NPO10538	Aspergillus fumigatus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO10538	Aspergillus fumigatus	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
GI50	2
IC50	19
Others	4

Activity Type	# Activity
Cell Line	25

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT2589	Cell Line	Panel leukemia (Carcinoma cell lines)	Homo sapiens	IC50	=	34673.69	nM	PMID[536064]
NPT6278	Cell Line	NSO	Mus musculus	IC50	=	52480.75	nM	PMID[536064]
NPT6511	Cell Line	Colon cells	Homo sapiens	IC50	=	53703.18	nM	PMID[536064]
NPT5530	Cell Line	CNS cells	Homo sapiens	IC50	=	43651.58	nM	PMID[536064]
NPT3880	Cell Line	Melanoma cells	Homo sapiens	IC50	=	47863.01	nM	PMID[536064]
NPT6428	Cell Line	Ovarian carcinoma cells	Homo sapiens	IC50	=	70794.58	nM	PMID[536064]
NPT6593	Cell Line	Renal cells	Homo sapiens	IC50	=	24547.09	nM	PMID[536064]
NPT6369	Cell Line	Prostate cells	Homo sapiens	IC50	=	50118.72	nM	PMID[536064]
NPT5230	Cell Line	Breast carcinoma cells	Homo sapiens	IC50	=	37153.52	nM	PMID[536064]
NPT6581	Cell Line	3Y1 cell line		GI50	=	43651.58	nM	PMID[536064]
NPT6581	Cell Line	3Y1 cell line		TGI	=	-4.02	n.a.	PMID[536064]
NPT6581	Cell Line	3Y1 cell line		LC50	>	-4.0	n.a.	PMID[536064]
NPT2589	Cell Line	Panel leukemia (Carcinoma cell lines)	Homo sapiens	IC50	=	69183.1	nM	PMID[536065]
NPT6278	Cell Line	NSO	Mus musculus	IC50	=	93325.43	nM	PMID[536065]
NPT6511	Cell Line	Colon cells	Homo sapiens	IC50	=	95499.26	nM	PMID[536065]
NPT5530	Cell Line	CNS cells	Homo sapiens	IC50	=	100000.0	nM	PMID[536065]
NPT3880	Cell Line	Melanoma cells	Homo sapiens	IC50	>	100000.0	nM	PMID[536065]
NPT6428	Cell Line	Ovarian carcinoma cells	Homo sapiens	IC50	>	100000.0	nM	PMID[536065]
NPT6593	Cell Line	Renal cells	Homo sapiens	IC50	>	100000.0	nM	PMID[536065]
NPT6369	Cell Line	Prostate cells	Homo sapiens	IC50	>	100000.0	nM	PMID[536065]
NPT5230	Cell Line	Breast carcinoma cells	Homo sapiens	IC50	>	100000.0	nM	PMID[536065]
NPT6581	Cell Line	3Y1 cell line		GI50	=	95499.26	nM	PMID[536065]
NPT6581	Cell Line	3Y1 cell line		TGI	>	4.0	n.a.	PMID[536065]
NPT6581	Cell Line	3Y1 cell line		LC50	>	-4.0	n.a.	PMID[536065]
NPT111	Cell Line	K562	Homo sapiens	IC50	=	41000.0	nM	PMID[536066]

☑ 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 NPC161861 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	480
0.1-0.2	3468
0.2-0.3	19552
0.3-0.4	12390
0.4-0.5	2387
0.5-0.6	2200
0.6-0.7	1557
0.7-0.8	602
0.8-0.85	50
0.85-0.9	9
0.9-0.95	1
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9119	High Similarity	NPC21174
0.9119	High Similarity	NPC271797
0.8976	High Similarity	NPC91179
0.8774	High Similarity	NPC470440
0.8765	High Similarity	NPC133003
0.8757	High Similarity	NPC470205
0.8704	High Similarity	NPC194881
0.8471	Intermediate Similarity	NPC11126
0.8457	Intermediate Similarity	NPC324091
0.8452	Intermediate Similarity	NPC88097
0.8448	Intermediate Similarity	NPC17059
0.8439	Intermediate Similarity	NPC99939
0.8439	Intermediate Similarity	NPC308931
0.8391	Intermediate Similarity	NPC17273
0.8391	Intermediate Similarity	NPC141612
0.8391	Intermediate Similarity	NPC135601
0.8382	Intermediate Similarity	NPC228835
0.8314	Intermediate Similarity	NPC469896
0.8295	Intermediate Similarity	NPC63199
0.8295	Intermediate Similarity	NPC196251
0.8295	Intermediate Similarity	NPC102338
0.8295	Intermediate Similarity	NPC175474
0.8295	Intermediate Similarity	NPC111602
0.8256	Intermediate Similarity	NPC219336
0.8249	Intermediate Similarity	NPC472112
0.8242	Intermediate Similarity	NPC474880
0.8242	Intermediate Similarity	NPC475990
0.8242	Intermediate Similarity	NPC221786
0.8207	Intermediate Similarity	NPC317701
0.8198	Intermediate Similarity	NPC183662
0.8198	Intermediate Similarity	NPC217372
0.8198	Intermediate Similarity	NPC15573
0.8194	Intermediate Similarity	NPC198988
0.8193	Intermediate Similarity	NPC229173
0.8156	Intermediate Similarity	NPC472113
0.8141	Intermediate Similarity	NPC325252
0.814	Intermediate Similarity	NPC151635
0.8118	Intermediate Similarity	NPC471943
0.8107	Intermediate Similarity	NPC56233
0.8101	Intermediate Similarity	NPC476460
0.8086	Intermediate Similarity	NPC21605
0.8079	Intermediate Similarity	NPC94752
0.8073	Intermediate Similarity	NPC305984
0.8072	Intermediate Similarity	NPC299594
0.8068	Intermediate Similarity	NPC21429
0.8011	Intermediate Similarity	NPC143533
0.8	Intermediate Similarity	NPC63157
0.8	Intermediate Similarity	NPC473868
0.7989	Intermediate Similarity	NPC213629
0.7978	Intermediate Similarity	NPC478077
0.7966	Intermediate Similarity	NPC472119
0.7966	Intermediate Similarity	NPC477003
0.7937	Intermediate Similarity	NPC59084
0.7937	Intermediate Similarity	NPC2949
0.7935	Intermediate Similarity	NPC52557
0.7935	Intermediate Similarity	NPC171317
0.7927	Intermediate Similarity	NPC470731
0.7923	Intermediate Similarity	NPC79356
0.7923	Intermediate Similarity	NPC102592
0.7907	Intermediate Similarity	NPC474897
0.7898	Intermediate Similarity	NPC15840
0.7898	Intermediate Similarity	NPC16659
0.7892	Intermediate Similarity	NPC281094
0.7889	Intermediate Similarity	NPC473666
0.7886	Intermediate Similarity	NPC145885
0.7886	Intermediate Similarity	NPC84827
0.7886	Intermediate Similarity	NPC14113
0.7882	Intermediate Similarity	NPC271734
0.7869	Intermediate Similarity	NPC19692
0.7869	Intermediate Similarity	NPC220151
0.7869	Intermediate Similarity	NPC294693
0.7857	Intermediate Similarity	NPC471386
0.7849	Intermediate Similarity	NPC254240
0.7849	Intermediate Similarity	NPC81654
0.7849	Intermediate Similarity	NPC317430
0.7849	Intermediate Similarity	NPC199851
0.7849	Intermediate Similarity	NPC128265
0.7849	Intermediate Similarity	NPC79129
0.7849	Intermediate Similarity	NPC195461
0.7849	Intermediate Similarity	NPC49196
0.7849	Intermediate Similarity	NPC294909
0.7849	Intermediate Similarity	NPC249150
0.7849	Intermediate Similarity	NPC313985
0.7849	Intermediate Similarity	NPC312870
0.7841	Intermediate Similarity	NPC265710
0.7838	Intermediate Similarity	NPC50503
0.7816	Intermediate Similarity	NPC252572
0.7816	Intermediate Similarity	NPC472123
0.7814	Intermediate Similarity	NPC81802
0.7814	Intermediate Similarity	NPC472210
0.7814	Intermediate Similarity	NPC247735
0.7814	Intermediate Similarity	NPC472295
0.7814	Intermediate Similarity	NPC269886
0.7799	Intermediate Similarity	NPC218268
0.7796	Intermediate Similarity	NPC220797
0.7796	Intermediate Similarity	NPC474318
0.7796	Intermediate Similarity	NPC475914
0.7796	Intermediate Similarity	NPC201266
0.7796	Intermediate Similarity	NPC268744
0.7796	Intermediate Similarity	NPC153123
0.7789	Intermediate Similarity	NPC54420
0.7784	Intermediate Similarity	NPC240088
0.7784	Intermediate Similarity	NPC284775
0.7784	Intermediate Similarity	NPC473380
0.7778	Intermediate Similarity	NPC473376
0.7771	Intermediate Similarity	NPC33421
0.7765	Intermediate Similarity	NPC472294
0.7765	Intermediate Similarity	NPC258480
0.7759	Intermediate Similarity	NPC6982
0.7754	Intermediate Similarity	NPC166209
0.7754	Intermediate Similarity	NPC269203
0.7754	Intermediate Similarity	NPC13456
0.7754	Intermediate Similarity	NPC77241
0.7753	Intermediate Similarity	NPC191415
0.7747	Intermediate Similarity	NPC329858
0.7747	Intermediate Similarity	NPC314333
0.7744	Intermediate Similarity	NPC204141
0.7744	Intermediate Similarity	NPC470732
0.7742	Intermediate Similarity	NPC474389
0.7733	Intermediate Similarity	NPC115232
0.773	Intermediate Similarity	NPC245916
0.773	Intermediate Similarity	NPC20144
0.7727	Intermediate Similarity	NPC280852
0.7722	Intermediate Similarity	NPC79062
0.7722	Intermediate Similarity	NPC472107
0.7717	Intermediate Similarity	NPC326422
0.7716	Intermediate Similarity	NPC115611
0.7713	Intermediate Similarity	NPC471944
0.7711	Intermediate Similarity	NPC37548
0.7708	Intermediate Similarity	NPC478158
0.7708	Intermediate Similarity	NPC162860
0.7707	Intermediate Similarity	NPC22079
0.7692	Intermediate Similarity	NPC321708
0.7688	Intermediate Similarity	NPC470509
0.7684	Intermediate Similarity	NPC234987
0.768	Intermediate Similarity	NPC66210
0.7679	Intermediate Similarity	NPC200214
0.7677	Intermediate Similarity	NPC272174
0.7663	Intermediate Similarity	NPC472292
0.764	Intermediate Similarity	NPC248041
0.764	Intermediate Similarity	NPC248462
0.764	Intermediate Similarity	NPC126709
0.7638	Intermediate Similarity	NPC474896
0.7637	Intermediate Similarity	NPC472323
0.7633	Intermediate Similarity	NPC476219
0.7627	Intermediate Similarity	NPC267885
0.7622	Intermediate Similarity	NPC304203
0.7619	Intermediate Similarity	NPC470233
0.7616	Intermediate Similarity	NPC214106
0.7611	Intermediate Similarity	NPC139291
0.7611	Intermediate Similarity	NPC472108
0.7611	Intermediate Similarity	NPC102755
0.7611	Intermediate Similarity	NPC117027
0.7607	Intermediate Similarity	NPC238499
0.7606	Intermediate Similarity	NPC293917
0.7604	Intermediate Similarity	NPC477065
0.7602	Intermediate Similarity	NPC478157
0.76	Intermediate Similarity	NPC31097
0.759	Intermediate Similarity	NPC478186
0.7582	Intermediate Similarity	NPC62749
0.7581	Intermediate Similarity	NPC57994
0.7581	Intermediate Similarity	NPC289299
0.7576	Intermediate Similarity	NPC242556
0.7574	Intermediate Similarity	NPC200743
0.7572	Intermediate Similarity	NPC478182
0.7571	Intermediate Similarity	NPC110500
0.7571	Intermediate Similarity	NPC203468
0.7571	Intermediate Similarity	NPC149155
0.756	Intermediate Similarity	NPC53947
0.7556	Intermediate Similarity	NPC113626
0.7553	Intermediate Similarity	NPC473640
0.7547	Intermediate Similarity	NPC475450
0.7546	Intermediate Similarity	NPC73767
0.7545	Intermediate Similarity	NPC179787
0.7545	Intermediate Similarity	NPC201380
0.7544	Intermediate Similarity	NPC76982
0.7542	Intermediate Similarity	NPC283219
0.754	Intermediate Similarity	NPC472293
0.754	Intermediate Similarity	NPC472116
0.753	Intermediate Similarity	NPC314372
0.7529	Intermediate Similarity	NPC38736
0.7529	Intermediate Similarity	NPC470507
0.7526	Intermediate Similarity	NPC475506
0.7515	Intermediate Similarity	NPC190296
0.7514	Intermediate Similarity	NPC473763
0.7514	Intermediate Similarity	NPC472097
0.7514	Intermediate Similarity	NPC117244
0.7514	Intermediate Similarity	NPC243716
0.7513	Intermediate Similarity	NPC100321
0.75	Intermediate Similarity	NPC469780
0.75	Intermediate Similarity	NPC469768
0.75	Intermediate Similarity	NPC469761
0.75	Intermediate Similarity	NPC65080
0.75	Intermediate Similarity	NPC469783
0.75	Intermediate Similarity	NPC469779
0.75	Intermediate Similarity	NPC187951
0.75	Intermediate Similarity	NPC88110
0.75	Intermediate Similarity	NPC75634
0.75	Intermediate Similarity	NPC227582
0.75	Intermediate Similarity	NPC167710

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 NPC161861 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	242
0.1-0.2	528
0.2-0.3	1037
0.3-0.4	1758
0.4-0.5	2171
0.5-0.6	2289
0.6-0.7	938
0.7-0.8	185
0.8-0.85	2
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8268	Intermediate Similarity	NPD7618	Phase 3
0.8268	Intermediate Similarity	NPD7619	Phase 3
0.7978	Intermediate Similarity	NPD2880	Discontinued
0.7978	Intermediate Similarity	NPD6664	Approved
0.795	Intermediate Similarity	NPD4637	Clinical (unspecified phase)
0.791	Intermediate Similarity	NPD3318	Approved
0.791	Intermediate Similarity	NPD3319	Phase 1
0.791	Intermediate Similarity	NPD3320	Approved
0.7901	Intermediate Similarity	NPD6180	Clinical (unspecified phase)
0.7877	Intermediate Similarity	NPD4426	Clinical (unspecified phase)
0.7872	Intermediate Similarity	NPD6288	Clinical (unspecified phase)
0.7849	Intermediate Similarity	NPD4500	Approved
0.7849	Intermediate Similarity	NPD4601	Approved
0.7849	Intermediate Similarity	NPD4501	Approved
0.7849	Intermediate Similarity	NPD4600	Approved
0.7841	Intermediate Similarity	NPD3078	Approved
0.7841	Intermediate Similarity	NPD3076	Approved
0.7841	Intermediate Similarity	NPD3077	Approved
0.7841	Intermediate Similarity	NPD2590	Clinical (unspecified phase)
0.7841	Intermediate Similarity	NPD3079	Approved
0.7836	Intermediate Similarity	NPD5744	Clinical (unspecified phase)
0.7829	Intermediate Similarity	NPD4075	Phase 2
0.7797	Intermediate Similarity	NPD5473	Discontinued
0.7789	Intermediate Similarity	NPD6838	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD3583	Phase 2
0.7765	Intermediate Similarity	NPD7564	Discontinued
0.7747	Intermediate Similarity	NPD4499	Approved
0.7716	Intermediate Similarity	NPD3943	Clinical (unspecified phase)
0.7709	Intermediate Similarity	NPD5728	Clinical (unspecified phase)
0.7697	Intermediate Similarity	NPD1683	Approved
0.7696	Intermediate Similarity	NPD8493	Clinical (unspecified phase)
0.768	Intermediate Similarity	NPD6217	Discontinued
0.7679	Intermediate Similarity	NPD2837	Discontinued
0.7667	Intermediate Similarity	NPD3607	Clinical (unspecified phase)
0.7665	Intermediate Similarity	NPD4462	Approved
0.7665	Intermediate Similarity	NPD4463	Approved
0.7661	Intermediate Similarity	NPD6454	Clinical (unspecified phase)
0.7656	Intermediate Similarity	NPD2443	Approved
0.7656	Intermediate Similarity	NPD2442	Approved
0.7637	Intermediate Similarity	NPD3961	Discontinued
0.763	Intermediate Similarity	NPD2915	Discontinued
0.7627	Intermediate Similarity	NPD4385	Clinical (unspecified phase)
0.7619	Intermediate Similarity	NPD7903	Clinical (unspecified phase)
0.7616	Intermediate Similarity	NPD6771	Discontinued
0.7614	Intermediate Similarity	NPD4112	Clinical (unspecified phase)
0.7609	Intermediate Similarity	NPD5592	Clinical (unspecified phase)
0.7606	Intermediate Similarity	NPD7621	Clinical (unspecified phase)
0.7598	Intermediate Similarity	NPD6277	Clinical (unspecified phase)
0.7592	Intermediate Similarity	NPD5426	Phase 3
0.759	Intermediate Similarity	NPD7594	Clinical (unspecified phase)
0.7581	Intermediate Similarity	NPD4602	Approved
0.7576	Intermediate Similarity	NPD5254	Discontinued
0.7571	Intermediate Similarity	NPD482	Approved
0.7562	Intermediate Similarity	NPD3385	Approved
0.7561	Intermediate Similarity	NPD1722	Approved
0.7546	Intermediate Similarity	NPD786	Approved
0.7544	Intermediate Similarity	NPD4326	Phase 2
0.7541	Intermediate Similarity	NPD6141	Clinical (unspecified phase)
0.7541	Intermediate Similarity	NPD3486	Clinical (unspecified phase)
0.7538	Intermediate Similarity	NPD5198	Approved
0.7538	Intermediate Similarity	NPD5199	Approved
0.7528	Intermediate Similarity	NPD5104	Approved
0.7528	Intermediate Similarity	NPD6044	Discontinued
0.7528	Intermediate Similarity	NPD749	Clinical (unspecified phase)
0.7514	Intermediate Similarity	NPD2095	Phase 2
0.7514	Intermediate Similarity	NPD2094	Phase 2
0.7514	Intermediate Similarity	NPD2092	Phase 2
0.7514	Intermediate Similarity	NPD6630	Clinical (unspecified phase)
0.7486	Intermediate Similarity	NPD5809	Phase 3
0.7486	Intermediate Similarity	NPD4643	Clinical (unspecified phase)
0.7476	Intermediate Similarity	NPD4885	Approved
0.7473	Intermediate Similarity	NPD7482	Phase 2
0.7473	Intermediate Similarity	NPD4922	Phase 2
0.7473	Intermediate Similarity	NPD2091	Phase 2
0.7473	Intermediate Similarity	NPD7483	Phase 2
0.7473	Intermediate Similarity	NPD2096	Phase 2
0.7456	Intermediate Similarity	NPD2172	Phase 1
0.7447	Intermediate Similarity	NPD6449	Clinical (unspecified phase)
0.7446	Intermediate Similarity	NPD2009	Clinical (unspecified phase)
0.7446	Intermediate Similarity	NPD6507	Clinical (unspecified phase)
0.7436	Intermediate Similarity	NPD2408	Discontinued
0.7433	Intermediate Similarity	NPD4348	Clinical (unspecified phase)
0.7423	Intermediate Similarity	NPD8322	Phase 2
0.7416	Intermediate Similarity	NPD750	Phase 2
0.7409	Intermediate Similarity	NPD8114	Approved
0.7409	Intermediate Similarity	NPD8115	Approved
0.7396	Intermediate Similarity	NPD3100	Discontinued
0.7391	Intermediate Similarity	NPD5820	Clinical (unspecified phase)
0.7389	Intermediate Similarity	NPD4181	Approved
0.7385	Intermediate Similarity	NPD7666	Phase 3
0.7385	Intermediate Similarity	NPD7665	Phase 2
0.7371	Intermediate Similarity	NPD3323	Discontinued
0.7366	Intermediate Similarity	NPD7730	Approved
0.7366	Intermediate Similarity	NPD7731	Approved
0.7362	Intermediate Similarity	NPD198	Clinical (unspecified phase)
0.736	Intermediate Similarity	NPD8013	Clinical (unspecified phase)
0.736	Intermediate Similarity	NPD7470	Discontinued
0.7356	Intermediate Similarity	NPD7950	Approved
0.7356	Intermediate Similarity	NPD7952	Approved
0.7356	Intermediate Similarity	NPD7953	Approved
0.7356	Intermediate Similarity	NPD7791	Approved
0.7356	Intermediate Similarity	NPD7790	Approved
0.7356	Intermediate Similarity	NPD7951	Approved
0.7356	Intermediate Similarity	NPD7789	Approved
0.7353	Intermediate Similarity	NPD7271	Approved
0.7345	Intermediate Similarity	NPD2185	Clinical (unspecified phase)
0.7345	Intermediate Similarity	NPD2844	Phase 3
0.7344	Intermediate Similarity	NPD5017	Discontinued
0.7337	Intermediate Similarity	NPD6610	Clinical (unspecified phase)
0.7337	Intermediate Similarity	NPD7970	Approved
0.7337	Intermediate Similarity	NPD7971	Clinical (unspecified phase)
0.733	Intermediate Similarity	NPD6249	Phase 2
0.733	Intermediate Similarity	NPD7781	Approved
0.733	Intermediate Similarity	NPD6248	Phase 2
0.733	Intermediate Similarity	NPD7780	Approved
0.7317	Intermediate Similarity	NPD200	Phase 2
0.7317	Intermediate Similarity	NPD201	Phase 2
0.7312	Intermediate Similarity	NPD3654	Approved
0.731	Intermediate Similarity	NPD7998	Clinical (unspecified phase)
0.7304	Intermediate Similarity	NPD7717	Approved
0.7304	Intermediate Similarity	NPD7716	Approved
0.7302	Intermediate Similarity	NPD7024	Clinical (unspecified phase)
0.7302	Intermediate Similarity	NPD7944	Discontinued
0.7295	Intermediate Similarity	NPD7824	Approved
0.7294	Intermediate Similarity	NPD4374	Clinical (unspecified phase)
0.7293	Intermediate Similarity	NPD6203	Clinical (unspecified phase)
0.7288	Intermediate Similarity	NPD2642	Approved
0.7288	Intermediate Similarity	NPD2639	Approved
0.7278	Intermediate Similarity	NPD5065	Approved
0.7278	Intermediate Similarity	NPD4128	Approved
0.7254	Intermediate Similarity	NPD7817	Phase 1
0.7251	Intermediate Similarity	NPD3835	Phase 3
0.7251	Intermediate Similarity	NPD3833	Phase 3
0.7247	Intermediate Similarity	NPD2641	Approved
0.7247	Intermediate Similarity	NPD1292	Clinical (unspecified phase)
0.7247	Intermediate Similarity	NPD2640	Approved
0.7247	Intermediate Similarity	NPD4779	Clinical (unspecified phase)
0.7245	Intermediate Similarity	NPD6328	Clinical (unspecified phase)
0.7243	Intermediate Similarity	NPD5075	Discontinued
0.724	Intermediate Similarity	NPD6999	Discontinued
0.724	Intermediate Similarity	NPD7000	Clinical (unspecified phase)
0.7236	Intermediate Similarity	NPD7656	Approved
0.7236	Intermediate Similarity	NPD7455	Approved
0.7236	Intermediate Similarity	NPD7657	Approved
0.7236	Intermediate Similarity	NPD7454	Approved
0.7235	Intermediate Similarity	NPD4547	Phase 3
0.7222	Intermediate Similarity	NPD3868	Phase 1
0.7222	Intermediate Similarity	NPD7809	Clinical (unspecified phase)
0.7219	Intermediate Similarity	NPD4334	Discontinued
0.7216	Intermediate Similarity	NPD1853	Clinical (unspecified phase)
0.7213	Intermediate Similarity	NPD8464	Clinical (unspecified phase)
0.7213	Intermediate Similarity	NPD6595	Phase 3
0.7208	Intermediate Similarity	NPD6459	Phase 2
0.7208	Intermediate Similarity	NPD2510	Approved
0.7208	Intermediate Similarity	NPD6376	Discontinued
0.7208	Intermediate Similarity	NPD2509	Approved
0.7204	Intermediate Similarity	NPD5444	Phase 1
0.7204	Intermediate Similarity	NPD7026	Phase 2
0.7198	Intermediate Similarity	NPD3505	Approved
0.7198	Intermediate Similarity	NPD3506	Approved
0.7194	Intermediate Similarity	NPD2008	Discontinued
0.7189	Intermediate Similarity	NPD6178	Phase 3
0.7188	Intermediate Similarity	NPD7204	Clinical (unspecified phase)
0.7179	Intermediate Similarity	NPD6176	Phase 1
0.7175	Intermediate Similarity	NPD5138	Approved
0.7175	Intermediate Similarity	NPD5140	Approved
0.7173	Intermediate Similarity	NPD4848	Phase 1
0.7167	Intermediate Similarity	NPD3609	Approved
0.7167	Intermediate Similarity	NPD3610	Approved
0.7165	Intermediate Similarity	NPD7727	Phase 2
0.7164	Intermediate Similarity	NPD3757	Clinical (unspecified phase)
0.7158	Intermediate Similarity	NPD4076	Approved
0.7158	Intermediate Similarity	NPD4079	Approved
0.7151	Intermediate Similarity	NPD5069	Clinical (unspecified phase)
0.715	Intermediate Similarity	NPD8093	Discontinued
0.715	Intermediate Similarity	NPD7308	Discontinued
0.715	Intermediate Similarity	NPD7603	Discontinued
0.7143	Intermediate Similarity	NPD8272	Phase 2
0.7143	Intermediate Similarity	NPD6263	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD8405	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD1658	Discontinued
0.7143	Intermediate Similarity	NPD6470	Phase 3
0.7143	Intermediate Similarity	NPD5020	Approved
0.7128	Intermediate Similarity	NPD6268	Phase 1
0.7128	Intermediate Similarity	NPD6269	Clinical (unspecified phase)
0.712	Intermediate Similarity	NPD5146	Suspended
0.712	Intermediate Similarity	NPD3927	Phase 2
0.7115	Intermediate Similarity	NPD6165	Phase 2
0.7115	Intermediate Similarity	NPD6164	Phase 2
0.7114	Intermediate Similarity	NPD6787	Phase 2
0.7111	Intermediate Similarity	NPD4184	Clinical (unspecified phase)
0.7109	Intermediate Similarity	NPD8047	Clinical (unspecified phase)
0.7108	Intermediate Similarity	NPD6554	Approved
0.7108	Intermediate Similarity	NPD45	Approved
0.7108	Intermediate Similarity	NPD1262	Discovery
0.7105	Intermediate Similarity	NPD5505	Discontinued
0.7104	Intermediate Similarity	NPD2144	Approved
0.7102	Intermediate Similarity	NPD2214	Approved
0.7102	Intermediate Similarity	NPD2213	Approved
0.7101	Intermediate Similarity	NPD4047	Discontinued

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