NPASS Compound

Structure

NPC308392 OpenBabel07101718182D 36 40 0 0 1 0 0 0 0 0999 V2000 5.1962 2.0000 0.0000 C 0 0 0 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 5.1962 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 1.5000 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 4.3301 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9282 2.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 7.7942 1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.0000 2.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 7.7942 0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 6.9282 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 5.1962 0.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -1.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 6.9282 3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 8.6603 2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 8.6603 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 0.5000 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 6.9282 -1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3 5 2 0 0 0 0 3 7 1 0 0 0 0 4 6 2 0 0 0 0 4 8 1 0 0 0 0 5 11 1 0 0 0 0 6 12 1 0 0 0 0 7 13 2 0 0 0 0 8 14 2 0 0 0 0 9 1 1 1 0 0 0 9 17 1 0 0 0 0 9 33 1 0 0 0 0 10 2 1 1 0 0 0 10 18 1 0 0 0 0 10 34 1 0 0 0 0 11 15 2 0 0 0 0 11 26 1 0 0 0 0 12 16 1 0 0 0 0 12 25 2 0 0 0 0 13 15 1 0 0 0 0 13 35 1 0 0 0 0 14 16 1 0 0 0 0 14 36 1 0 0 0 0 15 25 1 0 0 0 0 16 26 2 0 0 0 0 17 19 1 0 0 0 0 17 27 1 6 0 0 0 18 20 1 0 0 0 0 18 28 1 6 0 0 0 19 21 1 0 0 0 0 19 29 1 1 0 0 0 20 22 1 0 0 0 0 20 30 1 1 0 0 0 21 23 1 0 0 0 0 21 31 1 1 0 0 0 22 24 1 0 0 0 0 22 32 1 1 0 0 0 23 33 1 0 0 0 0 23 35 1 6 0 0 0 24 34 1 0 0 0 0 24 36 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	504.17
Volume:	472.318
LogP:	0.98
LogD:	0.057
LogS:	-4.563
# Rotatable Bonds:	4
TPSA:	184.08
# H-Bond Aceptor:	12
# H-Bond Donor:	6
# Rings:	5
# Heavy Atoms:	12

MedChem Properties

QED Drug-Likeness Score:	0.243
Synthetic Accessibility Score:	4.458
Fsp3:	0.5
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:	-6.387
MDCK Permeability:	4.087917841388844e-05
Pgp-inhibitor:	0.007
Pgp-substrate:	0.996
Human Intestinal Absorption (HIA):	0.349
20% Bioavailability (F20%):	0.001
30% Bioavailability (F30%):	0.98

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.065
Plasma Protein Binding (PPB):	90.65750885009766%
Volume Distribution (VD):	0.792
Pgp-substrate:	7.589847564697266%

ADMET: Metabolism

CYP1A2-inhibitor:	0.142
CYP1A2-substrate:	0.097
CYP2C19-inhibitor:	0.021
CYP2C19-substrate:	0.504
CYP2C9-inhibitor:	0.002
CYP2C9-substrate:	0.428
CYP2D6-inhibitor:	0.074
CYP2D6-substrate:	0.36
CYP3A4-inhibitor:	0.018
CYP3A4-substrate:	0.019

ADMET: Excretion

Clearance (CL):	1.113
Half-life (T1/2):	0.574

ADMET: Toxicity

hERG Blockers:	0.113
Human Hepatotoxicity (H-HT):	0.078
Drug-inuced Liver Injury (DILI):	0.897
AMES Toxicity:	0.515
Rat Oral Acute Toxicity:	0.028
Maximum Recommended Daily Dose:	0.006
Skin Sensitization:	0.151
Carcinogencity:	0.293
Eye Corrosion:	0.003
Eye Irritation:	0.015
Respiratory Toxicity:	0.399

Download Data

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

Natural Product: NPC308392

Natural Product ID:	NPC308392
*Common Name:**	Sophenazine F
IUPAC Name:	(2S,3R,4R,5R,6S)-2-methyl-6-[6-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyphenazin-1-yl]oxyoxane-3,4,5-triol
Synonyms:	Sophenazine F
Standard InCHIKey:	HHDAJEKYCDPELA-MQFMLQFSSA-N
Standard InCHI:	InChI=1S/C24H28N2O10/c1-9-17(27)19(29)21(31)23(33-9)35-13-7-3-5-11-15(13)25-12-6-4-8-14(16(12)26-11)36-24-22(32)20(30)18(28)10(2)34-24/h3-10,17-24,27-32H,1-2H3/t9-,10-,17-,18-,19+,20+,21+,22+,23-,24-/m0/s1
SMILES:	O[C@H]1[C@@H](O[C@H]([C@@H]([C@H]1O)O)C)Oc1cccc2c1nc1cccc(c1n2)O[C@@H]1O[C@@H](C)[C@@H]([C@H]([C@H]1O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2334063
PubChem CID:	71524394
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0004603] Organic oxygen compounds [CHEMONTID:0000323] Organooxygen compounds [CHEMONTID:0000011] Carbohydrates and carbohydrate conjugates [CHEMONTID:0002105] Glycosyl compounds [CHEMONTID:0004165] Phenolic glycosides

*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
NPO33439	streptomyces sp. strain dl-93	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[23317013]

☑ 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
MIC	9

Activity Type	# Activity
NON-MOLECULAR	2
Organism	8

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	EC50	=	45000.0	nM	PMID[500061]
NPT20	Organism	Candida albicans	Candida albicans	MIC	>	25.0	ug.mL-1	PMID[500061]
NPT85	Organism	Filobasidiella neoformans	Cryptococcus neoformans	MIC	>	25.0	ug.mL-1	PMID[500061]
NPT173	Organism	Klebsiella pneumoniae	Klebsiella pneumoniae	MIC	>	25.0	ug.mL-1	PMID[500061]
NPT18	Organism	Pseudomonas aeruginosa	Pseudomonas aeruginosa	MIC	>	25.0	ug.mL-1	PMID[500061]
NPT747	Organism	Acinetobacter baumannii	Acinetobacter baumannii	MIC	>	25.0	ug.mL-1	PMID[500061]
NPT19	Organism	Escherichia coli	Escherichia coli	MIC	>	25.0	ug.mL-1	PMID[500061]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	MIC	>	25.0	ug.mL-1	PMID[500061]
NPT175	Organism	Enterococcus faecalis	Enterococcus faecalis	MIC	>	25.0	ug.mL-1	PMID[500061]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	>	25.0	ug.mL-1	PMID[500061]

☑ 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 NPC308392 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	565
0.1-0.2	4826
0.2-0.3	11281
0.3-0.4	12454
0.4-0.5	10542
0.5-0.6	2550
0.6-0.7	429
0.7-0.8	43
0.8-0.85	4
0.85-0.9	2
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9365	High Similarity	NPC471736
0.8571	High Similarity	NPC110741
0.8548	High Similarity	NPC118776
0.8519	High Similarity	NPC310618
0.838	Intermediate Similarity	NPC124300
0.8341	Intermediate Similarity	NPC291609
0.8261	Intermediate Similarity	NPC1527
0.7833	Intermediate Similarity	NPC470586
0.7754	Intermediate Similarity	NPC79911
0.7701	Intermediate Similarity	NPC120798
0.7701	Intermediate Similarity	NPC285635
0.7696	Intermediate Similarity	NPC258773
0.7526	Intermediate Similarity	NPC95898
0.75	Intermediate Similarity	NPC472434
0.7488	Intermediate Similarity	NPC226202
0.7445	Intermediate Similarity	NPC99891
0.7383	Intermediate Similarity	NPC203168
0.7371	Intermediate Similarity	NPC219664
0.7363	Intermediate Similarity	NPC314573
0.7319	Intermediate Similarity	NPC472435
0.7317	Intermediate Similarity	NPC79293
0.7317	Intermediate Similarity	NPC279401
0.7294	Intermediate Similarity	NPC197141
0.7281	Intermediate Similarity	NPC288349
0.7269	Intermediate Similarity	NPC306644
0.7269	Intermediate Similarity	NPC236424
0.7249	Intermediate Similarity	NPC36168
0.7235	Intermediate Similarity	NPC274842
0.7227	Intermediate Similarity	NPC472436
0.7204	Intermediate Similarity	NPC66815
0.7164	Intermediate Similarity	NPC219963
0.7143	Intermediate Similarity	NPC244856
0.7119	Intermediate Similarity	NPC227824
0.7059	Intermediate Similarity	NPC42591
0.7059	Intermediate Similarity	NPC20249
0.703	Intermediate Similarity	NPC478023
0.701	Intermediate Similarity	NPC62069
0.6995	Remote Similarity	NPC161887
0.6995	Remote Similarity	NPC266551
0.6995	Remote Similarity	NPC112766
0.6991	Remote Similarity	NPC474595
0.6951	Remote Similarity	NPC148409
0.6944	Remote Similarity	NPC472111
0.6931	Remote Similarity	NPC220560
0.6931	Remote Similarity	NPC283152
0.6927	Remote Similarity	NPC469589
0.6916	Remote Similarity	NPC200888
0.6906	Remote Similarity	NPC469594
0.6881	Remote Similarity	NPC290069
0.6881	Remote Similarity	NPC194724
0.6872	Remote Similarity	NPC70549
0.6852	Remote Similarity	NPC469440
0.684	Remote Similarity	NPC469554
0.6833	Remote Similarity	NPC473800
0.6826	Remote Similarity	NPC476998
0.6826	Remote Similarity	NPC476996
0.682	Remote Similarity	NPC164374
0.682	Remote Similarity	NPC137929
0.6814	Remote Similarity	NPC90019
0.6802	Remote Similarity	NPC474594
0.6802	Remote Similarity	NPC471080
0.6802	Remote Similarity	NPC469592
0.6783	Remote Similarity	NPC476994
0.6783	Remote Similarity	NPC476997
0.6779	Remote Similarity	NPC204385
0.6771	Remote Similarity	NPC153452
0.6763	Remote Similarity	NPC320394
0.6757	Remote Similarity	NPC26679
0.6754	Remote Similarity	NPC470395
0.6752	Remote Similarity	NPC57453
0.6734	Remote Similarity	NPC118511
0.6733	Remote Similarity	NPC14651
0.6733	Remote Similarity	NPC121658
0.673	Remote Similarity	NPC469390
0.6725	Remote Similarity	NPC212766
0.6725	Remote Similarity	NPC289423
0.6716	Remote Similarity	NPC288943
0.6701	Remote Similarity	NPC26850
0.6683	Remote Similarity	NPC476518
0.6667	Remote Similarity	NPC110151
0.6667	Remote Similarity	NPC18487
0.6667	Remote Similarity	NPC470799
0.6667	Remote Similarity	NPC66083
0.6667	Remote Similarity	NPC8022
0.6667	Remote Similarity	NPC128823
0.6653	Remote Similarity	NPC476995
0.6652	Remote Similarity	NPC250448
0.6652	Remote Similarity	NPC470931
0.6651	Remote Similarity	NPC311357
0.6649	Remote Similarity	NPC470403
0.6649	Remote Similarity	NPC470404
0.6649	Remote Similarity	NPC470394
0.6636	Remote Similarity	NPC304183
0.6636	Remote Similarity	NPC476106
0.6624	Remote Similarity	NPC101543
0.6623	Remote Similarity	NPC128115
0.6622	Remote Similarity	NPC185782
0.6618	Remote Similarity	NPC478032
0.6598	Remote Similarity	NPC58209
0.6591	Remote Similarity	NPC118832
0.6591	Remote Similarity	NPC470930
0.6591	Remote Similarity	NPC47059
0.6591	Remote Similarity	NPC274291
0.6591	Remote Similarity	NPC165349
0.6591	Remote Similarity	NPC329708
0.6591	Remote Similarity	NPC264166
0.6587	Remote Similarity	NPC206201
0.6584	Remote Similarity	NPC165964
0.6582	Remote Similarity	NPC153769
0.6581	Remote Similarity	NPC476999
0.658	Remote Similarity	NPC473769
0.6579	Remote Similarity	NPC473179
0.6574	Remote Similarity	NPC267928
0.6574	Remote Similarity	NPC474188
0.6567	Remote Similarity	NPC314954
0.6561	Remote Similarity	NPC474145
0.6561	Remote Similarity	NPC475841
0.6548	Remote Similarity	NPC26872
0.6547	Remote Similarity	NPC209769
0.6545	Remote Similarity	NPC223427
0.654	Remote Similarity	NPC61350
0.6537	Remote Similarity	NPC111624
0.6533	Remote Similarity	NPC53069
0.6533	Remote Similarity	NPC202768
0.6533	Remote Similarity	NPC296482
0.6517	Remote Similarity	NPC177404
0.6511	Remote Similarity	NPC201508
0.6507	Remote Similarity	NPC213530
0.6507	Remote Similarity	NPC193267
0.6505	Remote Similarity	NPC312872
0.6504	Remote Similarity	NPC476287
0.649	Remote Similarity	NPC472168
0.6484	Remote Similarity	NPC11017
0.6478	Remote Similarity	NPC132642
0.6471	Remote Similarity	NPC245816
0.6471	Remote Similarity	NPC476138
0.6465	Remote Similarity	NPC141915
0.6465	Remote Similarity	NPC280964
0.6465	Remote Similarity	NPC114335
0.6463	Remote Similarity	NPC473822
0.646	Remote Similarity	NPC202605
0.646	Remote Similarity	NPC112206
0.6457	Remote Similarity	NPC313189
0.6456	Remote Similarity	NPC473182
0.6456	Remote Similarity	NPC96584
0.6456	Remote Similarity	NPC255800
0.6452	Remote Similarity	NPC473987
0.645	Remote Similarity	NPC310118
0.6446	Remote Similarity	NPC208364
0.6444	Remote Similarity	NPC167860
0.6444	Remote Similarity	NPC123976
0.6438	Remote Similarity	NPC473449
0.6435	Remote Similarity	NPC289786
0.6429	Remote Similarity	NPC475910
0.6425	Remote Similarity	NPC291535
0.6425	Remote Similarity	NPC475085
0.6425	Remote Similarity	NPC475112
0.6409	Remote Similarity	NPC315957
0.6409	Remote Similarity	NPC19872
0.64	Remote Similarity	NPC477548
0.6396	Remote Similarity	NPC475774
0.6395	Remote Similarity	NPC475271
0.6393	Remote Similarity	NPC72211
0.6391	Remote Similarity	NPC82070
0.6388	Remote Similarity	NPC171409
0.6388	Remote Similarity	NPC96405
0.6387	Remote Similarity	NPC329631
0.6386	Remote Similarity	NPC25899
0.6383	Remote Similarity	NPC473185
0.6379	Remote Similarity	NPC477795
0.6379	Remote Similarity	NPC477532
0.6379	Remote Similarity	NPC477806
0.6379	Remote Similarity	NPC477805
0.6379	Remote Similarity	NPC188400
0.6379	Remote Similarity	NPC477796
0.6379	Remote Similarity	NPC160100
0.6378	Remote Similarity	NPC161292
0.6376	Remote Similarity	NPC473053
0.6375	Remote Similarity	NPC184680
0.6375	Remote Similarity	NPC473183
0.6372	Remote Similarity	NPC314834
0.6371	Remote Similarity	NPC475253
0.6368	Remote Similarity	NPC21638
0.6368	Remote Similarity	NPC36229
0.6368	Remote Similarity	NPC16452
0.6368	Remote Similarity	NPC476581
0.6364	Remote Similarity	NPC475844
0.6364	Remote Similarity	NPC52254
0.636	Remote Similarity	NPC473184
0.6359	Remote Similarity	NPC475190
0.6356	Remote Similarity	NPC287208
0.6355	Remote Similarity	NPC206251
0.6355	Remote Similarity	NPC74382
0.6349	Remote Similarity	NPC470785
0.6347	Remote Similarity	NPC70956
0.6347	Remote Similarity	NPC478049
0.6347	Remote Similarity	NPC243834
0.6347	Remote Similarity	NPC314948
0.6341	Remote Similarity	NPC173250
0.6339	Remote Similarity	NPC309498

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 NPC308392 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	308
0.1-0.2	782
0.2-0.3	1178
0.3-0.4	2543
0.4-0.5	2861
0.5-0.6	1263
0.6-0.7	214
0.7-0.8	1
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
0.7282	Intermediate Similarity	NPD6861	Clinical (unspecified phase)
0.7264	Intermediate Similarity	NPD5083	Clinical (unspecified phase)
0.7244	Intermediate Similarity	NPD7284	Clinical (unspecified phase)
0.7116	Intermediate Similarity	NPD5863	Clinical (unspecified phase)
0.711	Intermediate Similarity	NPD2772	Clinical (unspecified phase)
0.711	Intermediate Similarity	NPD2314	Clinical (unspecified phase)
0.7081	Intermediate Similarity	NPD6550	Discontinued
0.7039	Intermediate Similarity	NPD8117	Approved
0.7039	Intermediate Similarity	NPD8116	Phase 3
0.7035	Intermediate Similarity	NPD6553	Clinical (unspecified phase)
0.699	Remote Similarity	NPD6393	Clinical (unspecified phase)
0.6951	Remote Similarity	NPD7194	Discontinued
0.6944	Remote Similarity	NPD3003	Approved
0.6923	Remote Similarity	NPD5903	Approved
0.6923	Remote Similarity	NPD5902	Approved
0.6916	Remote Similarity	NPD7426	Phase 1
0.6916	Remote Similarity	NPD7676	Clinical (unspecified phase)
0.6916	Remote Similarity	NPD7674	Phase 3
0.6916	Remote Similarity	NPD7675	Phase 3
0.6891	Remote Similarity	NPD8324	Phase 2
0.6889	Remote Similarity	NPD6298	Discontinued
0.6887	Remote Similarity	NPD1622	Discontinued
0.6872	Remote Similarity	NPD6590	Discontinued
0.6864	Remote Similarity	NPD4131	Phase 3
0.6864	Remote Similarity	NPD4502	Phase 2
0.6847	Remote Similarity	NPD5417	Clinical (unspecified phase)
0.6844	Remote Similarity	NPD5930	Phase 3
0.684	Remote Similarity	NPD774	Phase 3
0.6829	Remote Similarity	NPD4204	Approved
0.6829	Remote Similarity	NPD4203	Approved
0.6822	Remote Similarity	NPD1768	Approved
0.681	Remote Similarity	NPD7558	Phase 2
0.6789	Remote Similarity	NPD5530	Phase 1
0.6777	Remote Similarity	NPD4372	Phase 1
0.6777	Remote Similarity	NPD6569	Phase 2
0.6769	Remote Similarity	NPD5640	Discontinued
0.6761	Remote Similarity	NPD3477	Phase 2
0.6761	Remote Similarity	NPD3478	Clinical (unspecified phase)
0.6756	Remote Similarity	NPD6985	Discontinued
0.6738	Remote Similarity	NPD6494	Phase 2
0.6712	Remote Similarity	NPD2540	Clinical (unspecified phase)
0.671	Remote Similarity	NPD8104	Phase 3
0.6699	Remote Similarity	NPD5256	Discontinued
0.6683	Remote Similarity	NPD4724	Clinical (unspecified phase)
0.6682	Remote Similarity	NPD5512	Phase 3
0.6682	Remote Similarity	NPD7222	Phase 2
0.6667	Remote Similarity	NPD1033	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD1034	Phase 3
0.6652	Remote Similarity	NPD3875	Discontinued
0.6651	Remote Similarity	NPD6769	Clinical (unspecified phase)
0.6651	Remote Similarity	NPD6988	Phase 1
0.6636	Remote Similarity	NPD6491	Clinical (unspecified phase)
0.6621	Remote Similarity	NPD6669	Phase 2
0.6608	Remote Similarity	NPD8109	Clinical (unspecified phase)
0.6606	Remote Similarity	NPD1392	Approved
0.6604	Remote Similarity	NPD4081	Clinical (unspecified phase)
0.6598	Remote Similarity	NPD8359	Phase 2
0.6593	Remote Similarity	NPD2433	Clinical (unspecified phase)
0.6591	Remote Similarity	NPD4035	Approved
0.6591	Remote Similarity	NPD32	Approved
0.6591	Remote Similarity	NPD4037	Approved
0.6591	Remote Similarity	NPD4036	Approved
0.6591	Remote Similarity	NPD4122	Approved
0.6591	Remote Similarity	NPD4034	Approved
0.6591	Remote Similarity	NPD4039	Approved
0.6591	Remote Similarity	NPD31	Approved
0.6591	Remote Similarity	NPD4033	Approved
0.6591	Remote Similarity	NPD4038	Approved
0.6568	Remote Similarity	NPD3838	Phase 3
0.6564	Remote Similarity	NPD1744	Approved
0.6561	Remote Similarity	NPD4305	Clinical (unspecified phase)
0.6548	Remote Similarity	NPD789	Phase 2
0.6537	Remote Similarity	NPD6306	Phase 2
0.6533	Remote Similarity	NPD3816	Phase 1
0.6533	Remote Similarity	NPD3815	Phase 1
0.6532	Remote Similarity	NPD5429	Discontinued
0.6531	Remote Similarity	NPD7859	Phase 2
0.6526	Remote Similarity	NPD8063	Discontinued
0.652	Remote Similarity	NPD565	Phase 2
0.6518	Remote Similarity	NPD8244	Phase 2
0.6516	Remote Similarity	NPD5482	Discontinued
0.6512	Remote Similarity	NPD6814	Phase 3
0.6504	Remote Similarity	NPD8370	Discontinued
0.6494	Remote Similarity	NPD1856	Discontinued
0.649	Remote Similarity	NPD3920	Phase 2
0.649	Remote Similarity	NPD3370	Clinical (unspecified phase)
0.6489	Remote Similarity	NPD3570	Phase 2
0.6489	Remote Similarity	NPD5416	Discontinued
0.6486	Remote Similarity	NPD3842	Clinical (unspecified phase)
0.6481	Remote Similarity	NPD1603	Discontinued
0.6481	Remote Similarity	NPD1602	Discontinued
0.6473	Remote Similarity	NPD6716	Phase 1
0.6468	Remote Similarity	NPD8512	Phase 3
0.6463	Remote Similarity	NPD5632	Approved
0.6457	Remote Similarity	NPD7452	Approved
0.6457	Remote Similarity	NPD7453	Approved
0.6457	Remote Similarity	NPD6290	Phase 2
0.6453	Remote Similarity	NPD6326	Phase 2
0.6449	Remote Similarity	NPD6525	Clinical (unspecified phase)
0.6447	Remote Similarity	NPD8510	Clinical (unspecified phase)
0.6438	Remote Similarity	NPD5547	Clinical (unspecified phase)
0.6438	Remote Similarity	NPD6246	Approved
0.6435	Remote Similarity	NPD2785	Clinical (unspecified phase)
0.6429	Remote Similarity	NPD5658	Approved
0.6429	Remote Similarity	NPD3074	Discontinued
0.6425	Remote Similarity	NPD5938	Phase 3
0.6423	Remote Similarity	NPD6503	Clinical (unspecified phase)
0.6417	Remote Similarity	NPD7729	Clinical (unspecified phase)
0.6416	Remote Similarity	NPD7703	Clinical (unspecified phase)
0.6409	Remote Similarity	NPD1740	Approved
0.6409	Remote Similarity	NPD1739	Approved
0.6404	Remote Similarity	NPD7538	Clinical (unspecified phase)
0.6404	Remote Similarity	NPD863	Approved
0.6404	Remote Similarity	NPD861	Approved
0.6404	Remote Similarity	NPD862	Approved
0.6402	Remote Similarity	NPD4021	Phase 2
0.6394	Remote Similarity	NPD4498	Clinical (unspecified phase)
0.6393	Remote Similarity	NPD772	Phase 3
0.6391	Remote Similarity	NPD7395	Discontinued
0.639	Remote Similarity	NPD7025	Clinical (unspecified phase)
0.6388	Remote Similarity	NPD7069	Discontinued
0.6388	Remote Similarity	NPD4927	Discontinued
0.6387	Remote Similarity	NPD4080	Discontinued
0.6387	Remote Similarity	NPD6741	Clinical (unspecified phase)
0.6386	Remote Similarity	NPD8255	Phase 2
0.6383	Remote Similarity	NPD6327	Phase 1
0.638	Remote Similarity	NPD6592	Clinical (unspecified phase)
0.6379	Remote Similarity	NPD7726	Phase 1
0.6376	Remote Similarity	NPD5101	Discontinued
0.6375	Remote Similarity	NPD4368	Phase 2
0.6368	Remote Similarity	NPD4795	Phase 2
0.6368	Remote Similarity	NPD3946	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD6159	Phase 2
0.6348	Remote Similarity	NPD5059	Clinical (unspecified phase)
0.6345	Remote Similarity	NPD8442	Discontinued
0.6344	Remote Similarity	NPD5067	Phase 2
0.6344	Remote Similarity	NPD7468	Clinical (unspecified phase)
0.6344	Remote Similarity	NPD6220	Phase 3
0.6344	Remote Similarity	NPD5066	Phase 2
0.6338	Remote Similarity	NPD6227	Discontinued
0.6337	Remote Similarity	NPD6060	Clinical (unspecified phase)
0.6335	Remote Similarity	NPD4396	Clinical (unspecified phase)
0.6329	Remote Similarity	NPD5022	Discontinued
0.6322	Remote Similarity	NPD2921	Clinical (unspecified phase)
0.6322	Remote Similarity	NPD4858	Phase 2
0.6316	Remote Similarity	NPD4354	Approved
0.6313	Remote Similarity	NPD4324	Phase 2
0.6313	Remote Similarity	NPD4325	Phase 2
0.6311	Remote Similarity	NPD6573	Phase 3
0.6311	Remote Similarity	NPD6572	Phase 2
0.6304	Remote Similarity	NPD6643	Discontinued
0.6303	Remote Similarity	NPD6962	Phase 2
0.6303	Remote Similarity	NPD1505	Phase 2
0.63	Remote Similarity	NPD4900	Clinical (unspecified phase)
0.6296	Remote Similarity	NPD5316	Approved
0.6295	Remote Similarity	NPD5102	Clinical (unspecified phase)
0.6293	Remote Similarity	NPD6974	Phase 3
0.6292	Remote Similarity	NPD6964	Approved
0.6292	Remote Similarity	NPD6963	Approved
0.629	Remote Similarity	NPD2175	Phase 3
0.629	Remote Similarity	NPD2176	Approved
0.629	Remote Similarity	NPD2958	Clinical (unspecified phase)
0.629	Remote Similarity	NPD2177	Approved
0.6288	Remote Similarity	NPD7571	Clinical (unspecified phase)
0.6282	Remote Similarity	NPD6824	Clinical (unspecified phase)
0.6282	Remote Similarity	NPD6736	Discontinued
0.6281	Remote Similarity	NPD8330	Clinical (unspecified phase)
0.6278	Remote Similarity	NPD6477	Clinical (unspecified phase)
0.6275	Remote Similarity	NPD5450	Discontinued
0.6275	Remote Similarity	NPD7012	Phase 3
0.6275	Remote Similarity	NPD7013	Phase 3
0.6273	Remote Similarity	NPD4604	Approved
0.6273	Remote Similarity	NPD2476	Clinical (unspecified phase)
0.6273	Remote Similarity	NPD4605	Approved
0.6272	Remote Similarity	NPD3939	Suspended
0.627	Remote Similarity	NPD7022	Phase 2
0.627	Remote Similarity	NPD7955	Approved
0.627	Remote Similarity	NPD7956	Approved
0.6265	Remote Similarity	NPD6743	Phase 2
0.6265	Remote Similarity	NPD6742	Phase 2
0.6264	Remote Similarity	NPD8421	Discontinued
0.6262	Remote Similarity	NPD4889	Approved
0.6261	Remote Similarity	NPD6140	Clinical (unspecified phase)
0.6261	Remote Similarity	NPD7589	Clinical (unspecified phase)
0.6261	Remote Similarity	NPD4667	Clinical (unspecified phase)
0.626	Remote Similarity	NPD5488	Discontinued
0.6256	Remote Similarity	NPD3324	Clinical (unspecified phase)
0.6255	Remote Similarity	NPD7548	Discontinued
0.625	Remote Similarity	NPD2215	Approved
0.625	Remote Similarity	NPD2216	Approved
0.6245	Remote Similarity	NPD7413	Phase 3
0.6245	Remote Similarity	NPD1941	Approved
0.6245	Remote Similarity	NPD7620	Phase 2
0.6245	Remote Similarity	NPD7067	Approved
0.6245	Remote Similarity	NPD7068	Approved
0.6244	Remote Similarity	NPD7889	Clinical (unspecified phase)
0.6239	Remote Similarity	NPD3924	Approved
0.6239	Remote Similarity	NPD3922	Approved
0.6239	Remote Similarity	NPD3923	Approved
0.6239	Remote Similarity	NPD4881	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