NPASS Compound

Structure

NPC474544 OpenBabel07101718322D 23 24 0 0 1 0 0 0 0 0999 V2000 0.0496 -2.4375 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5830 -2.2556 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9600 1.6628 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8392 0.1808 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.7655 -0.1286 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9342 -0.6086 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.7655 0.8314 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1028 -0.1286 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9342 1.3114 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7285 -1.7587 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1028 0.8314 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2714 1.3114 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.4400 -0.8314 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4800 0.8314 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4400 0.8314 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.4800 -0.8314 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.9200 -0.0000 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 2.2714 2.2714 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.9200 -1.6628 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.4400 1.7914 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 1.6628 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.4718 -0.7061 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 10 1 0 0 0 0 2 10 1 0 0 0 0 3 22 1 0 0 0 0 4 23 1 0 0 0 0 5 6 2 0 0 0 0 5 7 1 0 0 0 0 6 8 1 0 0 0 0 7 9 2 0 0 0 0 8 11 2 0 0 0 0 9 11 1 0 0 0 0 11 12 1 0 0 0 0 12 15 1 0 0 0 0 12 19 1 6 0 0 0 13 16 1 0 0 0 0 13 17 2 0 0 0 0 13 20 1 0 0 0 0 14 15 1 0 0 0 0 14 18 2 0 0 0 0 14 22 1 0 0 0 0 15 17 1 0 0 0 0 15 21 1 1 0 0 0 16 10 1 6 0 0 0 16 18 1 0 0 0 0 16 23 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	322.15
Volume:	320.942
LogP:	1.445
LogD:	1.338
LogS:	-2.06
# Rotatable Bonds:	5
TPSA:	100.38
# H-Bond Aceptor:	7
# H-Bond Donor:	3
# Rings:	2
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.753
Synthetic Accessibility Score:	4.325
Fsp3:	0.5
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
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:	-4.722
MDCK Permeability:	2.9536455258494243e-05
Pgp-inhibitor:	0.009
Pgp-substrate:	0.125
Human Intestinal Absorption (HIA):	0.017
20% Bioavailability (F20%):	0.006
30% Bioavailability (F30%):	0.141

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.981
Plasma Protein Binding (PPB):	64.03254699707031%
Volume Distribution (VD):	1.466
Pgp-substrate:	42.449317932128906%

ADMET: Metabolism

CYP1A2-inhibitor:	0.031
CYP1A2-substrate:	0.238
CYP2C19-inhibitor:	0.039
CYP2C19-substrate:	0.89
CYP2C9-inhibitor:	0.026
CYP2C9-substrate:	0.079
CYP2D6-inhibitor:	0.002
CYP2D6-substrate:	0.276
CYP3A4-inhibitor:	0.022
CYP3A4-substrate:	0.86

ADMET: Excretion

Clearance (CL):	5.28
Half-life (T1/2):	0.786

ADMET: Toxicity

hERG Blockers:	0.01
Human Hepatotoxicity (H-HT):	0.925
Drug-inuced Liver Injury (DILI):	0.919
AMES Toxicity:	0.223
Rat Oral Acute Toxicity:	0.04
Maximum Recommended Daily Dose:	0.835
Skin Sensitization:	0.247
Carcinogencity:	0.039
Eye Corrosion:	0.003
Eye Irritation:	0.031
Respiratory Toxicity:	0.03

Download Data

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

Natural Product: NPC474544

Natural Product ID:	NPC474544
*Common Name:**	Terezine C
IUPAC Name:	(3R,6R)-6-hydroxy-6-[(R)-hydroxy(phenyl)methyl]-3,5-dimethoxy-3-propan-2-yl-1H-pyrazin-2-one
Synonyms:	Terezine C
Standard InCHIKey:	GOQWKAOJTXJMMW-DAXOMENPSA-N
Standard InCHI:	InChI=1S/C16H22N2O5/c1-10(2)16(23-4)13(20)17-15(21,14(18-16)22-3)12(19)11-8-6-5-7-9-11/h5-10,12,19,21H,1-4H3,(H,17,20)/t12-,15-,16-/m1/s1
SMILES:	COC1=N[C@@](OC)(C(C)C)C(=N[C@@]1(O)[C@@H](c1ccccc1)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL471598
PubChem CID:	10041796
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000264] Organic acids and derivatives [CHEMONTID:0000265] Carboxylic acids and derivatives [CHEMONTID:0000013] Amino acids, peptides, and analogues [CHEMONTID:0000347] Amino acids and derivatives [CHEMONTID:0000060] Alpha amino acids 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
NPO19344	Sporormiella teretispora	Species	Sporormiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[7760082]
NPO19344	Sporormiella teretispora	Species	Sporormiaceae	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
Others	3

Activity Type	# Activity
Organism	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT79	Organism	Bacillus subtilis	Bacillus subtilis	IZ	=	8.0	mm	PMID[495944]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	IZ	=	8.0	mm	PMID[495944]
NPT3095	Organism	Sordaria fimicola	Sordaria fimicola	Activity	=	41.0	%	PMID[495944]

☑ 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 NPC474544 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	114
0.1-0.2	776
0.2-0.3	3637
0.3-0.4	13082
0.4-0.5	15540
0.5-0.6	8260
0.6-0.7	1143
0.7-0.8	143
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC1986
0.8036	Intermediate Similarity	NPC211551
0.7788	Intermediate Similarity	NPC113326
0.7788	Intermediate Similarity	NPC224610
0.7788	Intermediate Similarity	NPC194390
0.7788	Intermediate Similarity	NPC88267
0.7787	Intermediate Similarity	NPC476183
0.776	Intermediate Similarity	NPC474479
0.7731	Intermediate Similarity	NPC118202
0.7724	Intermediate Similarity	NPC476184
0.7724	Intermediate Similarity	NPC476281
0.7706	Intermediate Similarity	NPC161972
0.7706	Intermediate Similarity	NPC303045
0.7706	Intermediate Similarity	NPC58674
0.7679	Intermediate Similarity	NPC214200
0.7679	Intermediate Similarity	NPC228400
0.7623	Intermediate Similarity	NPC237420
0.76	Intermediate Similarity	NPC476278
0.7576	Intermediate Similarity	NPC6570
0.7541	Intermediate Similarity	NPC311737
0.7541	Intermediate Similarity	NPC38458
0.754	Intermediate Similarity	NPC476241
0.754	Intermediate Similarity	NPC476260
0.7523	Intermediate Similarity	NPC265521
0.7521	Intermediate Similarity	NPC317254
0.75	Intermediate Similarity	NPC226096
0.75	Intermediate Similarity	NPC290515
0.75	Intermediate Similarity	NPC190663
0.75	Intermediate Similarity	NPC164514
0.75	Intermediate Similarity	NPC108606
0.75	Intermediate Similarity	NPC303611
0.748	Intermediate Similarity	NPC476179
0.748	Intermediate Similarity	NPC476125
0.7477	Intermediate Similarity	NPC25565
0.7459	Intermediate Similarity	NPC82963
0.7431	Intermediate Similarity	NPC226438
0.7422	Intermediate Similarity	NPC278097
0.7411	Intermediate Similarity	NPC475439
0.7411	Intermediate Similarity	NPC311242
0.7411	Intermediate Similarity	NPC33168
0.7411	Intermediate Similarity	NPC473501
0.7387	Intermediate Similarity	NPC20142
0.7387	Intermediate Similarity	NPC215351
0.7381	Intermediate Similarity	NPC160493
0.736	Intermediate Similarity	NPC477061
0.736	Intermediate Similarity	NPC45777
0.735	Intermediate Similarity	NPC136962
0.7344	Intermediate Similarity	NPC4974
0.7344	Intermediate Similarity	NPC325013
0.7339	Intermediate Similarity	NPC314992
0.7328	Intermediate Similarity	NPC150254
0.7328	Intermediate Similarity	NPC147000
0.7328	Intermediate Similarity	NPC304761
0.7328	Intermediate Similarity	NPC226778
0.7317	Intermediate Similarity	NPC2265
0.7313	Intermediate Similarity	NPC64205
0.7311	Intermediate Similarity	NPC65855
0.7311	Intermediate Similarity	NPC292758
0.7308	Intermediate Similarity	NPC259098
0.7308	Intermediate Similarity	NPC197680
0.7308	Intermediate Similarity	NPC101372
0.7304	Intermediate Similarity	NPC327226
0.728	Intermediate Similarity	NPC283760
0.7264	Intermediate Similarity	NPC304538
0.7258	Intermediate Similarity	NPC169328
0.725	Intermediate Similarity	NPC474149
0.7244	Intermediate Similarity	NPC474862
0.7238	Intermediate Similarity	NPC103326
0.7238	Intermediate Similarity	NPC99394
0.7238	Intermediate Similarity	NPC329319
0.7238	Intermediate Similarity	NPC87299
0.7226	Intermediate Similarity	NPC168861
0.7222	Intermediate Similarity	NPC198747
0.7222	Intermediate Similarity	NPC80150
0.7203	Intermediate Similarity	NPC475203
0.7203	Intermediate Similarity	NPC472315
0.7203	Intermediate Similarity	NPC231705
0.7203	Intermediate Similarity	NPC472316
0.7203	Intermediate Similarity	NPC474376
0.72	Intermediate Similarity	NPC310467
0.7188	Intermediate Similarity	NPC35996
0.7182	Intermediate Similarity	NPC172128
0.7179	Intermediate Similarity	NPC171831
0.7179	Intermediate Similarity	NPC242913
0.7179	Intermediate Similarity	NPC280616
0.7176	Intermediate Similarity	NPC477839
0.7176	Intermediate Similarity	NPC295478
0.7167	Intermediate Similarity	NPC258056
0.7154	Intermediate Similarity	NPC29477
0.7153	Intermediate Similarity	NPC197921
0.7143	Intermediate Similarity	NPC45191
0.7143	Intermediate Similarity	NPC117180
0.7131	Intermediate Similarity	NPC273814
0.7101	Intermediate Similarity	NPC91953
0.7101	Intermediate Similarity	NPC469360
0.7099	Intermediate Similarity	NPC210950
0.7099	Intermediate Similarity	NPC199738
0.7097	Intermediate Similarity	NPC37302
0.7077	Intermediate Similarity	NPC472414
0.7077	Intermediate Similarity	NPC47667
0.7077	Intermediate Similarity	NPC95733
0.7077	Intermediate Similarity	NPC62101
0.7069	Intermediate Similarity	NPC469457
0.7064	Intermediate Similarity	NPC211237
0.7063	Intermediate Similarity	NPC476744
0.7059	Intermediate Similarity	NPC37115
0.7054	Intermediate Similarity	NPC472415
0.7049	Intermediate Similarity	NPC234376
0.7045	Intermediate Similarity	NPC469666
0.704	Intermediate Similarity	NPC258992
0.7037	Intermediate Similarity	NPC228511
0.7037	Intermediate Similarity	NPC99482
0.7015	Intermediate Similarity	NPC275538
0.7015	Intermediate Similarity	NPC473724
0.7008	Intermediate Similarity	NPC43275
0.7008	Intermediate Similarity	NPC14950
0.7008	Intermediate Similarity	NPC268572
0.7	Intermediate Similarity	NPC142297
0.7	Intermediate Similarity	NPC211218
0.6993	Remote Similarity	NPC476743
0.6992	Remote Similarity	NPC265002
0.6985	Remote Similarity	NPC113325
0.6985	Remote Similarity	NPC279045
0.6978	Remote Similarity	NPC83289
0.6978	Remote Similarity	NPC108852
0.6978	Remote Similarity	NPC477838
0.6978	Remote Similarity	NPC212850
0.6978	Remote Similarity	NPC111586
0.6978	Remote Similarity	NPC189724
0.6978	Remote Similarity	NPC477837
0.6978	Remote Similarity	NPC261709
0.6967	Remote Similarity	NPC323007
0.6964	Remote Similarity	NPC245259
0.6963	Remote Similarity	NPC471953
0.6957	Remote Similarity	NPC312770
0.6957	Remote Similarity	NPC204848
0.6957	Remote Similarity	NPC160607
0.6957	Remote Similarity	NPC41473
0.6957	Remote Similarity	NPC14600
0.6957	Remote Similarity	NPC471201
0.6953	Remote Similarity	NPC478014
0.6953	Remote Similarity	NPC478015
0.6953	Remote Similarity	NPC478016
0.695	Remote Similarity	NPC178466
0.695	Remote Similarity	NPC63628
0.6949	Remote Similarity	NPC178902
0.6942	Remote Similarity	NPC114741
0.6942	Remote Similarity	NPC153690
0.6942	Remote Similarity	NPC24101
0.6942	Remote Similarity	NPC182549
0.6942	Remote Similarity	NPC96224
0.6937	Remote Similarity	NPC1793
0.6937	Remote Similarity	NPC470877
0.6935	Remote Similarity	NPC120217
0.6934	Remote Similarity	NPC127741
0.6923	Remote Similarity	NPC316797
0.6923	Remote Similarity	NPC245974
0.6918	Remote Similarity	NPC476741
0.6917	Remote Similarity	NPC71271
0.6917	Remote Similarity	NPC296712
0.6916	Remote Similarity	NPC475199
0.6916	Remote Similarity	NPC283012
0.6912	Remote Similarity	NPC132847
0.6912	Remote Similarity	NPC477680
0.6906	Remote Similarity	NPC299583
0.6894	Remote Similarity	NPC65310
0.6889	Remote Similarity	NPC114102
0.6875	Remote Similarity	NPC471307
0.6875	Remote Similarity	NPC121872
0.6875	Remote Similarity	NPC141139
0.6875	Remote Similarity	NPC78041
0.6875	Remote Similarity	NPC74936
0.6875	Remote Similarity	NPC209764
0.6875	Remote Similarity	NPC159178
0.687	Remote Similarity	NPC307020
0.687	Remote Similarity	NPC3371
0.6864	Remote Similarity	NPC40258
0.6864	Remote Similarity	NPC91461
0.6864	Remote Similarity	NPC7686
0.6864	Remote Similarity	NPC318154
0.686	Remote Similarity	NPC277788
0.6852	Remote Similarity	NPC172984
0.685	Remote Similarity	NPC266389
0.685	Remote Similarity	NPC216605
0.685	Remote Similarity	NPC122245
0.6849	Remote Similarity	NPC476742
0.6846	Remote Similarity	NPC252878
0.6833	Remote Similarity	NPC37714
0.6833	Remote Similarity	NPC154899
0.6833	Remote Similarity	NPC233396
0.6833	Remote Similarity	NPC152384
0.6831	Remote Similarity	NPC49565
0.6829	Remote Similarity	NPC30563
0.6825	Remote Similarity	NPC235421
0.6818	Remote Similarity	NPC93843
0.6812	Remote Similarity	NPC68865
0.6812	Remote Similarity	NPC175870
0.6807	Remote Similarity	NPC160382
0.6806	Remote Similarity	NPC132771
0.6797	Remote Similarity	NPC5932

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 NPC474544 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	108
0.1-0.2	472
0.2-0.3	926
0.3-0.4	2432
0.4-0.5	3073
0.5-0.6	1670
0.6-0.7	443
0.7-0.8	26
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
0.7611	Intermediate Similarity	NPD855	Approved
0.7611	Intermediate Similarity	NPD854	Approved
0.75	Intermediate Similarity	NPD9611	Approved
0.75	Intermediate Similarity	NPD9612	Approved
0.75	Intermediate Similarity	NPD9609	Approved
0.75	Intermediate Similarity	NPD5723	Approved
0.7458	Intermediate Similarity	NPD9713	Approved
0.7436	Intermediate Similarity	NPD6406	Approved
0.7339	Intermediate Similarity	NPD2218	Phase 2
0.7339	Intermediate Similarity	NPD2217	Approved
0.7328	Intermediate Similarity	NPD315	Approved
0.7328	Intermediate Similarity	NPD179	Clinical (unspecified phase)
0.7328	Intermediate Similarity	NPD314	Approved
0.7328	Intermediate Similarity	NPD309	Approved
0.7328	Intermediate Similarity	NPD10	Approved
0.7328	Intermediate Similarity	NPD311	Approved
0.7328	Intermediate Similarity	NPD310	Approved
0.7328	Intermediate Similarity	NPD4738	Phase 2
0.7323	Intermediate Similarity	NPD5108	Clinical (unspecified phase)
0.7288	Intermediate Similarity	NPD4095	Clinical (unspecified phase)
0.725	Intermediate Similarity	NPD2583	Phase 2
0.7217	Intermediate Similarity	NPD4760	Clinical (unspecified phase)
0.7207	Intermediate Similarity	NPD752	Approved
0.7197	Intermediate Similarity	NPD3136	Phase 2
0.7177	Intermediate Similarity	NPD3123	Discovery
0.7143	Intermediate Similarity	NPD719	Approved
0.7143	Intermediate Similarity	NPD720	Approved
0.7143	Intermediate Similarity	NPD1080	Approved
0.7132	Intermediate Similarity	NPD3676	Clinical (unspecified phase)
0.7107	Intermediate Similarity	NPD4025	Clinical (unspecified phase)
0.708	Intermediate Similarity	NPD4814	Discontinued
0.7059	Intermediate Similarity	NPD810	Approved
0.7059	Intermediate Similarity	NPD811	Approved
0.7059	Intermediate Similarity	NPD812	Approved
0.704	Intermediate Similarity	NPD6775	Clinical (unspecified phase)
0.7009	Intermediate Similarity	NPD4817	Approved
0.7009	Intermediate Similarity	NPD4818	Approved
0.6984	Remote Similarity	NPD7522	Discontinued
0.6967	Remote Similarity	NPD4254	Approved
0.6967	Remote Similarity	NPD4253	Approved
0.696	Remote Similarity	NPD7508	Discontinued
0.6957	Remote Similarity	NPD1875	Phase 1
0.6929	Remote Similarity	NPD2227	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD2549	Approved
0.6923	Remote Similarity	NPD2550	Approved
0.6923	Remote Similarity	NPD2555	Approved
0.6923	Remote Similarity	NPD2553	Approved
0.6923	Remote Similarity	NPD2552	Approved
0.6923	Remote Similarity	NPD2558	Approved
0.6906	Remote Similarity	NPD4172	Approved
0.6906	Remote Similarity	NPD4173	Approved
0.6903	Remote Similarity	NPD1812	Approved
0.6903	Remote Similarity	NPD1814	Approved
0.6903	Remote Similarity	NPD6690	Approved
0.6903	Remote Similarity	NPD159	Clinical (unspecified phase)
0.6894	Remote Similarity	NPD2159	Approved
0.6894	Remote Similarity	NPD2160	Approved
0.6894	Remote Similarity	NPD2628	Approved
0.6894	Remote Similarity	NPD2625	Approved
0.6894	Remote Similarity	NPD2627	Approved
0.6894	Remote Similarity	NPD2626	Approved
0.6894	Remote Similarity	NPD2579	Approved
0.687	Remote Similarity	NPD4659	Approved
0.6864	Remote Similarity	NPD4189	Approved
0.6864	Remote Similarity	NPD4719	Phase 2
0.6864	Remote Similarity	NPD4188	Approved
0.686	Remote Similarity	NPD9532	Phase 3
0.6846	Remote Similarity	NPD4806	Approved
0.6846	Remote Similarity	NPD4807	Approved
0.6846	Remote Similarity	NPD4480	Approved
0.6842	Remote Similarity	NPD3718	Approved
0.6842	Remote Similarity	NPD7451	Discontinued
0.6842	Remote Similarity	NPD3719	Approved
0.6838	Remote Similarity	NPD840	Approved
0.6838	Remote Similarity	NPD839	Approved
0.6838	Remote Similarity	NPD5729	Clinical (unspecified phase)
0.6822	Remote Similarity	NPD7342	Discontinued
0.6814	Remote Similarity	NPD530	Approved
0.6807	Remote Similarity	NPD3682	Approved
0.6807	Remote Similarity	NPD4229	Approved
0.6807	Remote Similarity	NPD1542	Approved
0.6807	Remote Similarity	NPD3683	Approved
0.6807	Remote Similarity	NPD4231	Approved
0.6807	Remote Similarity	NPD3681	Approved
0.6807	Remote Similarity	NPD3680	Approved
0.6794	Remote Similarity	NPD2562	Approved
0.6794	Remote Similarity	NPD2561	Approved
0.6791	Remote Similarity	NPD767	Phase 1
0.6783	Remote Similarity	NPD7274	Clinical (unspecified phase)
0.6769	Remote Similarity	NPD4136	Approved
0.6769	Remote Similarity	NPD4106	Approved
0.6769	Remote Similarity	NPD4135	Approved
0.6765	Remote Similarity	NPD3056	Clinical (unspecified phase)
0.6763	Remote Similarity	NPD3553	Approved
0.6763	Remote Similarity	NPD3552	Approved
0.6763	Remote Similarity	NPD3555	Approved
0.6763	Remote Similarity	NPD3554	Approved
0.6762	Remote Similarity	NPD9294	Approved
0.6757	Remote Similarity	NPD9538	Approved
0.675	Remote Similarity	NPD3046	Approved
0.675	Remote Similarity	NPD3048	Approved
0.675	Remote Similarity	NPD3047	Approved
0.6748	Remote Similarity	NPD9380	Clinical (unspecified phase)
0.6748	Remote Similarity	NPD550	Approved
0.6748	Remote Similarity	NPD551	Approved
0.6746	Remote Similarity	NPD9614	Approved
0.6746	Remote Similarity	NPD2629	Approved
0.6746	Remote Similarity	NPD9618	Approved
0.6744	Remote Similarity	NPD1710	Approved
0.6742	Remote Similarity	NPD3685	Discontinued
0.6741	Remote Similarity	NPD4617	Approved
0.6741	Remote Similarity	NPD5203	Approved
0.6741	Remote Similarity	NPD4620	Approved
0.6741	Remote Similarity	NPD5202	Clinical (unspecified phase)
0.6741	Remote Similarity	NPD5201	Approved
0.6738	Remote Similarity	NPD7978	Discontinued
0.6723	Remote Similarity	NPD1540	Approved
0.6721	Remote Similarity	NPD6038	Clinical (unspecified phase)
0.6719	Remote Similarity	NPD828	Approved
0.6719	Remote Similarity	NPD317	Approved
0.6719	Remote Similarity	NPD318	Approved
0.6719	Remote Similarity	NPD16	Approved
0.6719	Remote Similarity	NPD856	Approved
0.6711	Remote Similarity	NPD8070	Approved
0.6696	Remote Similarity	NPD531	Approved
0.6696	Remote Similarity	NPD1101	Approved
0.6695	Remote Similarity	NPD9712	Approved
0.6694	Remote Similarity	NPD999	Phase 2
0.6692	Remote Similarity	NPD5305	Approved
0.6692	Remote Similarity	NPD7725	Approved
0.6692	Remote Similarity	NPD5306	Approved
0.6692	Remote Similarity	NPD5238	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD3663	Approved
0.6667	Remote Similarity	NPD5204	Approved
0.6667	Remote Similarity	NPD5119	Approved
0.6667	Remote Similarity	NPD3662	Phase 3
0.6667	Remote Similarity	NPD2229	Approved
0.6667	Remote Similarity	NPD3661	Approved
0.6667	Remote Similarity	NPD4658	Approved
0.6667	Remote Similarity	NPD2228	Approved
0.6667	Remote Similarity	NPD5121	Approved
0.6667	Remote Similarity	NPD5120	Approved
0.6667	Remote Similarity	NPD5595	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD5700	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD2234	Approved
0.6667	Remote Similarity	NPD6624	Discontinued
0.6667	Remote Similarity	NPD3664	Approved
0.6667	Remote Similarity	NPD4656	Approved
0.6642	Remote Similarity	NPD4619	Approved
0.6642	Remote Similarity	NPD1048	Approved
0.6642	Remote Similarity	NPD4103	Phase 2
0.6642	Remote Similarity	NPD4104	Clinical (unspecified phase)
0.6642	Remote Similarity	NPD4621	Approved
0.6641	Remote Similarity	NPD3421	Phase 3
0.6639	Remote Similarity	NPD3524	Approved
0.6639	Remote Similarity	NPD3526	Approved
0.6639	Remote Similarity	NPD2559	Approved
0.6639	Remote Similarity	NPD2551	Approved
0.662	Remote Similarity	NPD2174	Clinical (unspecified phase)
0.662	Remote Similarity	NPD4152	Approved
0.6615	Remote Similarity	NPD4105	Approved
0.6615	Remote Similarity	NPD4102	Approved
0.6615	Remote Similarity	NPD770	Discontinued
0.661	Remote Similarity	NPD9711	Approved
0.661	Remote Similarity	NPD9710	Approved
0.661	Remote Similarity	NPD9495	Approved
0.6599	Remote Similarity	NPD7527	Clinical (unspecified phase)
0.6599	Remote Similarity	NPD52	Approved
0.6599	Remote Similarity	NPD7526	Approved
0.6597	Remote Similarity	NPD2575	Approved
0.6597	Remote Similarity	NPD6331	Phase 2
0.6597	Remote Similarity	NPD6676	Phase 2
0.6594	Remote Similarity	NPD1423	Approved
0.6594	Remote Similarity	NPD2674	Phase 3
0.6591	Remote Similarity	NPD3974	Phase 2
0.6591	Remote Similarity	NPD5350	Clinical (unspecified phase)
0.6591	Remote Similarity	NPD2173	Clinical (unspecified phase)
0.6591	Remote Similarity	NPD5338	Clinical (unspecified phase)
0.6591	Remote Similarity	NPD5351	Clinical (unspecified phase)
0.6589	Remote Similarity	NPD1758	Phase 1
0.6589	Remote Similarity	NPD9616	Approved
0.6589	Remote Similarity	NPD9615	Approved
0.6589	Remote Similarity	NPD1359	Approved
0.6589	Remote Similarity	NPD9613	Approved
0.6583	Remote Similarity	NPD4119	Approved
0.6562	Remote Similarity	NPD1348	Approved
0.656	Remote Similarity	NPD3642	Approved
0.656	Remote Similarity	NPD3643	Approved
0.656	Remote Similarity	NPD3644	Approved
0.6557	Remote Similarity	NPD5717	Approved
0.6552	Remote Similarity	NPD1066	Discontinued
0.6544	Remote Similarity	NPD4993	Discontinued
0.6541	Remote Similarity	NPD4273	Approved
0.6538	Remote Similarity	NPD1759	Phase 1
0.6538	Remote Similarity	NPD316	Approved
0.6532	Remote Similarity	NPD4717	Approved
0.6532	Remote Similarity	NPD4720	Approved
0.6532	Remote Similarity	NPD4718	Approved
0.6525	Remote Similarity	NPD6852	Discontinued
0.6522	Remote Similarity	NPD3144	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