NPASS Compound

Structure

NPC310618 OpenBabel07101718272D 38 42 0 0 1 0 0 0 0 0999 V2000 3.4641 -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 1.7321 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 5.0000 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 2.5981 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 0.5000 0.0000 C 0 0 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 0.8660 1.5000 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 2.5981 3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 3.5000 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 3.4641 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 0.0000 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 6.0622 0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.7321 -1.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 6.0622 1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.7321 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.0000 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 2.0000 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 1.7321 3.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 2.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 -1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.9282 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.9282 2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 0.5000 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 4.3301 1.5000 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 5.1962 3.0000 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 3 5 2 0 0 0 0 3 6 1 0 0 0 0 4 7 2 0 0 0 0 4 8 1 0 0 0 0 5 11 1 0 0 0 0 6 12 2 0 0 0 0 7 13 1 0 0 0 0 8 14 2 0 0 0 0 9 1 1 6 0 0 0 9 17 1 0 0 0 0 9 35 1 0 0 0 0 10 2 1 1 0 0 0 10 18 1 0 0 0 0 10 36 1 0 0 0 0 11 15 2 0 0 0 0 11 23 1 0 0 0 0 12 15 1 0 0 0 0 12 27 1 0 0 0 0 13 16 1 0 0 0 0 13 26 2 0 0 0 0 14 16 1 0 0 0 0 14 37 1 0 0 0 0 15 26 1 0 0 0 0 16 27 2 0 0 0 0 17 19 1 0 0 0 0 17 28 1 1 0 0 0 18 20 1 0 0 0 0 18 29 1 6 0 0 0 19 21 1 0 0 0 0 19 30 1 6 0 0 0 20 22 1 0 0 0 0 20 31 1 1 0 0 0 21 24 1 0 0 0 0 21 32 1 6 0 0 0 22 25 1 0 0 0 0 22 33 1 1 0 0 0 23 34 2 0 0 0 0 23 38 1 0 0 0 0 24 35 1 0 0 0 0 24 37 1 1 0 0 0 25 36 1 0 0 0 0 25 38 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	532.17
Volume:	495.768
LogP:	0.861
LogD:	0.051
LogS:	-4.508
# Rotatable Bonds:	5
TPSA:	201.15
# H-Bond Aceptor:	13
# H-Bond Donor:	6
# Rings:	5
# Heavy Atoms:	13

MedChem Properties

QED Drug-Likeness Score:	0.176
Synthetic Accessibility Score:	4.524
Fsp3:	0.48
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:	-6.346
MDCK Permeability:	5.521393904928118e-05
Pgp-inhibitor:	0.01
Pgp-substrate:	0.996
Human Intestinal Absorption (HIA):	0.625
20% Bioavailability (F20%):	0.001
30% Bioavailability (F30%):	0.988

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.099
Plasma Protein Binding (PPB):	92.42057800292969%
Volume Distribution (VD):	0.914
Pgp-substrate:	7.830225467681885%

ADMET: Metabolism

CYP1A2-inhibitor:	0.158
CYP1A2-substrate:	0.068
CYP2C19-inhibitor:	0.022
CYP2C19-substrate:	0.295
CYP2C9-inhibitor:	0.003
CYP2C9-substrate:	0.278
CYP2D6-inhibitor:	0.075
CYP2D6-substrate:	0.188
CYP3A4-inhibitor:	0.018
CYP3A4-substrate:	0.013

ADMET: Excretion

Clearance (CL):	1.298
Half-life (T1/2):	0.525

ADMET: Toxicity

hERG Blockers:	0.128
Human Hepatotoxicity (H-HT):	0.135
Drug-inuced Liver Injury (DILI):	0.953
AMES Toxicity:	0.252
Rat Oral Acute Toxicity:	0.011
Maximum Recommended Daily Dose:	0.005
Skin Sensitization:	0.086
Carcinogencity:	0.078
Eye Corrosion:	0.003
Eye Irritation:	0.024
Respiratory Toxicity:	0.1

Download Data

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

Natural Product: NPC310618

Natural Product ID:	NPC310618
*Common Name:**	Sophenazine D
IUPAC Name:	[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl] 6-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyphenazine-1-carboxylate
Synonyms:	Sophenazine D
Standard InCHIKey:	NWTDQEJBZQIDSM-MDDLDUBOSA-N
Standard InCHI:	InChI=1S/C25H28N2O11/c1-9-17(28)19(30)21(32)24(35-9)37-14-8-4-7-13-16(14)27-12-6-3-5-11(15(12)26-13)23(34)38-25-22(33)20(31)18(29)10(2)36-25/h3-10,17-22,24-25,28-33H,1-2H3/t9-,10-,17-,18-,19+,20+,21+,22+,24-,25-/m0/s1
SMILES:	C[C@H]1[C@@H]([C@H]([C@H]([C@@H](O1)Oc1cccc2c1nc1cccc(c1n2)C(=O)O[C@H]1[C@@H]([C@@H]([C@H]([C@H](C)O1)O)O)O)O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2334061
PubChem CID:	71524392
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
MIC	9

Activity Type	# Activity
NON-MOLECULAR	1
Organism	8

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT20	Organism	Candida albicans	Candida albicans	MIC	>	25.0	ug.mL-1	PMID[551728]
NPT85	Organism	Filobasidiella neoformans	Cryptococcus neoformans	MIC	>	25.0	ug.mL-1	PMID[551728]
NPT173	Organism	Klebsiella pneumoniae	Klebsiella pneumoniae	MIC	>	25.0	ug.mL-1	PMID[551728]
NPT18	Organism	Pseudomonas aeruginosa	Pseudomonas aeruginosa	MIC	>	25.0	ug.mL-1	PMID[551728]
NPT747	Organism	Acinetobacter baumannii	Acinetobacter baumannii	MIC	>	25.0	ug.mL-1	PMID[551728]
NPT19	Organism	Escherichia coli	Escherichia coli	MIC	>	25.0	ug.mL-1	PMID[551728]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	MIC	>	25.0	ug.mL-1	PMID[551728]
NPT175	Organism	Enterococcus faecalis	Enterococcus faecalis	MIC	>	25.0	ug.mL-1	PMID[551728]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	>	25.0	ug.mL-1	PMID[551728]

☑ 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 NPC310618 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	477
0.1-0.2	2483
0.2-0.3	10161
0.3-0.4	8917
0.4-0.5	14507
0.5-0.6	4842
0.6-0.7	1201
0.7-0.8	97
0.8-0.85	5
0.85-0.9	4
0.9-0.95	0
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9861	High Similarity	NPC124300
0.9816	High Similarity	NPC291609
0.875	High Similarity	NPC236424
0.875	High Similarity	NPC306644
0.871	High Similarity	NPC274842
0.8618	High Similarity	NPC244856
0.8519	High Similarity	NPC308392
0.8436	Intermediate Similarity	NPC227824
0.8009	Intermediate Similarity	NPC471736
0.7909	Intermediate Similarity	NPC470586
0.7846	Intermediate Similarity	NPC472435
0.7788	Intermediate Similarity	NPC314834
0.7768	Intermediate Similarity	NPC314855
0.7768	Intermediate Similarity	NPC313796
0.7768	Intermediate Similarity	NPC315638
0.7768	Intermediate Similarity	NPC313345
0.7751	Intermediate Similarity	NPC472436
0.7733	Intermediate Similarity	NPC314297
0.7733	Intermediate Similarity	NPC315545
0.7724	Intermediate Similarity	NPC473800
0.7664	Intermediate Similarity	NPC472434
0.7611	Intermediate Similarity	NPC165964
0.7593	Intermediate Similarity	NPC57453
0.7566	Intermediate Similarity	NPC314648
0.7541	Intermediate Similarity	NPC99891
0.7489	Intermediate Similarity	NPC110741
0.7477	Intermediate Similarity	NPC90415
0.746	Intermediate Similarity	NPC218388
0.7454	Intermediate Similarity	NPC118776
0.7419	Intermediate Similarity	NPC58209
0.7385	Intermediate Similarity	NPC203635
0.7382	Intermediate Similarity	NPC250448
0.7366	Intermediate Similarity	NPC329631
0.7339	Intermediate Similarity	NPC243058
0.7328	Intermediate Similarity	NPC475844
0.7281	Intermediate Similarity	NPC256268
0.7269	Intermediate Similarity	NPC208364
0.7235	Intermediate Similarity	NPC219848
0.7217	Intermediate Similarity	NPC317572
0.7214	Intermediate Similarity	NPC101312
0.72	Intermediate Similarity	NPC160100
0.72	Intermediate Similarity	NPC188400
0.7191	Intermediate Similarity	NPC203168
0.7189	Intermediate Similarity	NPC148889
0.7179	Intermediate Similarity	NPC219664
0.7162	Intermediate Similarity	NPC314573
0.716	Intermediate Similarity	NPC258048
0.716	Intermediate Similarity	NPC166712
0.7155	Intermediate Similarity	NPC309498
0.7154	Intermediate Similarity	NPC173250
0.7143	Intermediate Similarity	NPC312645
0.7126	Intermediate Similarity	NPC34770
0.7124	Intermediate Similarity	NPC279401
0.7124	Intermediate Similarity	NPC79293
0.7088	Intermediate Similarity	NPC152620
0.7078	Intermediate Similarity	NPC97746
0.7077	Intermediate Similarity	NPC215837
0.7073	Intermediate Similarity	NPC474688
0.7054	Intermediate Similarity	NPC53534
0.7048	Intermediate Similarity	NPC230403
0.7047	Intermediate Similarity	NPC161801
0.7037	Intermediate Similarity	NPC1527
0.7029	Intermediate Similarity	NPC288349
0.7023	Intermediate Similarity	NPC132385
0.702	Intermediate Similarity	NPC140296
0.702	Intermediate Similarity	NPC270515
0.7017	Intermediate Similarity	NPC89508
0.7016	Intermediate Similarity	NPC478045
0.7012	Intermediate Similarity	NPC168922
0.7012	Intermediate Similarity	NPC298436
0.7009	Intermediate Similarity	NPC194040
0.7004	Intermediate Similarity	NPC260434
0.6996	Remote Similarity	NPC100734
0.6996	Remote Similarity	NPC88923
0.6996	Remote Similarity	NPC315634
0.6992	Remote Similarity	NPC274640
0.6988	Remote Similarity	NPC120513
0.6983	Remote Similarity	NPC128115
0.6974	Remote Similarity	NPC196449
0.6974	Remote Similarity	NPC314222
0.6971	Remote Similarity	NPC131885
0.6971	Remote Similarity	NPC82070
0.6971	Remote Similarity	NPC184408
0.697	Remote Similarity	NPC280714
0.6969	Remote Similarity	NPC208522
0.6967	Remote Similarity	NPC205372
0.6967	Remote Similarity	NPC475271
0.6967	Remote Similarity	NPC314633
0.6965	Remote Similarity	NPC67401
0.6953	Remote Similarity	NPC66815
0.6944	Remote Similarity	NPC41501
0.6942	Remote Similarity	NPC52254
0.6939	Remote Similarity	NPC21638
0.6935	Remote Similarity	NPC284685
0.6933	Remote Similarity	NPC146418
0.6926	Remote Similarity	NPC203373
0.6926	Remote Similarity	NPC144452
0.692	Remote Similarity	NPC182222
0.692	Remote Similarity	NPC328928
0.6911	Remote Similarity	NPC200888
0.691	Remote Similarity	NPC328559
0.6908	Remote Similarity	NPC49547
0.6904	Remote Similarity	NPC111732
0.6901	Remote Similarity	NPC174576
0.6899	Remote Similarity	NPC473188
0.6891	Remote Similarity	NPC473639
0.6888	Remote Similarity	NPC152768
0.6888	Remote Similarity	NPC148183
0.6883	Remote Similarity	NPC74575
0.6875	Remote Similarity	NPC39500
0.687	Remote Similarity	NPC473449
0.6867	Remote Similarity	NPC217176
0.6867	Remote Similarity	NPC474701
0.6867	Remote Similarity	NPC79223
0.6863	Remote Similarity	NPC172355
0.6863	Remote Similarity	NPC316224
0.6848	Remote Similarity	NPC1608
0.6844	Remote Similarity	NPC191489
0.6844	Remote Similarity	NPC320394
0.6842	Remote Similarity	NPC144381
0.6838	Remote Similarity	NPC32451
0.6831	Remote Similarity	NPC314270
0.682	Remote Similarity	NPC269367
0.682	Remote Similarity	NPC475301
0.682	Remote Similarity	NPC326930
0.6818	Remote Similarity	NPC476114
0.6814	Remote Similarity	NPC42591
0.6813	Remote Similarity	NPC473105
0.6809	Remote Similarity	NPC311357
0.6805	Remote Similarity	NPC232225
0.6803	Remote Similarity	NPC148409
0.6803	Remote Similarity	NPC208084
0.6802	Remote Similarity	NPC179287
0.6794	Remote Similarity	NPC13603
0.6793	Remote Similarity	NPC472287
0.6793	Remote Similarity	NPC472286
0.6793	Remote Similarity	NPC472111
0.6792	Remote Similarity	NPC87413
0.6786	Remote Similarity	NPC327769
0.6781	Remote Similarity	NPC324245
0.6781	Remote Similarity	NPC320748
0.6778	Remote Similarity	NPC469589
0.6776	Remote Similarity	NPC469439
0.6776	Remote Similarity	NPC472099
0.6774	Remote Similarity	NPC473506
0.6773	Remote Similarity	NPC30456
0.6772	Remote Similarity	NPC101350
0.677	Remote Similarity	NPC62069
0.6765	Remote Similarity	NPC474595
0.6765	Remote Similarity	NPC156044
0.6765	Remote Similarity	NPC474905
0.6765	Remote Similarity	NPC193238
0.6765	Remote Similarity	NPC244741
0.6763	Remote Similarity	NPC264176
0.6762	Remote Similarity	NPC469594
0.6761	Remote Similarity	NPC51388
0.6759	Remote Similarity	NPC473187
0.6756	Remote Similarity	NPC85879
0.6756	Remote Similarity	NPC303374
0.6756	Remote Similarity	NPC53255
0.6748	Remote Similarity	NPC60621
0.6747	Remote Similarity	NPC248903
0.6742	Remote Similarity	NPC129897
0.6733	Remote Similarity	NPC475303
0.6733	Remote Similarity	NPC475596
0.6732	Remote Similarity	NPC472061
0.6732	Remote Similarity	NPC184680
0.6732	Remote Similarity	NPC235685
0.6732	Remote Similarity	NPC470022
0.6729	Remote Similarity	NPC471978
0.6729	Remote Similarity	NPC209981
0.6721	Remote Similarity	NPC148124
0.672	Remote Similarity	NPC471977
0.672	Remote Similarity	NPC471762
0.672	Remote Similarity	NPC475644
0.672	Remote Similarity	NPC471190
0.672	Remote Similarity	NPC470486
0.6717	Remote Similarity	NPC185197
0.6717	Remote Similarity	NPC473833
0.6709	Remote Similarity	NPC317672
0.6709	Remote Similarity	NPC59033
0.6708	Remote Similarity	NPC16066
0.6708	Remote Similarity	NPC118228
0.6707	Remote Similarity	NPC470018
0.6707	Remote Similarity	NPC174760
0.6707	Remote Similarity	NPC225279
0.6707	Remote Similarity	NPC26928
0.6706	Remote Similarity	NPC474192
0.6706	Remote Similarity	NPC475720
0.6706	Remote Similarity	NPC470785
0.6706	Remote Similarity	NPC469554
0.6696	Remote Similarity	NPC283152
0.6695	Remote Similarity	NPC4687
0.6695	Remote Similarity	NPC321428
0.6694	Remote Similarity	NPC472098
0.6694	Remote Similarity	NPC122436
0.6694	Remote Similarity	NPC94842
0.6694	Remote Similarity	NPC174788
0.6694	Remote Similarity	NPC197141
0.6692	Remote Similarity	NPC91868

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 NPC310618 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	300
0.1-0.2	625
0.2-0.3	1132
0.3-0.4	2070
0.4-0.5	2849
0.5-0.6	1711
0.6-0.7	442
0.7-0.8	21
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
0.7965	Intermediate Similarity	NPD5417	Clinical (unspecified phase)
0.7675	Intermediate Similarity	NPD5416	Discontinued
0.7582	Intermediate Similarity	NPD6716	Phase 1
0.7427	Intermediate Similarity	NPD6962	Phase 2
0.7404	Intermediate Similarity	NPD5632	Approved
0.7366	Intermediate Similarity	NPD6741	Clinical (unspecified phase)
0.735	Intermediate Similarity	NPD7538	Clinical (unspecified phase)
0.7349	Intermediate Similarity	NPD5488	Discontinued
0.7333	Intermediate Similarity	NPD5640	Discontinued
0.7331	Intermediate Similarity	NPD5482	Discontinued
0.7314	Intermediate Similarity	NPD5022	Discontinued
0.7261	Intermediate Similarity	NPD7426	Phase 1
0.7258	Intermediate Similarity	NPD7417	Discontinued
0.7257	Intermediate Similarity	NPD7395	Discontinued
0.7231	Intermediate Similarity	NPD7268	Clinical (unspecified phase)
0.7224	Intermediate Similarity	NPD4373	Phase 2
0.7222	Intermediate Similarity	NPD7703	Clinical (unspecified phase)
0.7213	Intermediate Similarity	NPD7284	Clinical (unspecified phase)
0.7212	Intermediate Similarity	NPD5512	Phase 3
0.7212	Intermediate Similarity	NPD6550	Discontinued
0.7173	Intermediate Similarity	NPD2433	Clinical (unspecified phase)
0.7149	Intermediate Similarity	NPD2921	Clinical (unspecified phase)
0.7126	Intermediate Similarity	NPD6525	Clinical (unspecified phase)
0.7102	Intermediate Similarity	NPD4952	Phase 3
0.7097	Intermediate Similarity	NPD7853	Phase 2
0.7095	Intermediate Similarity	NPD6298	Discontinued
0.7078	Intermediate Similarity	NPD3925	Approved
0.7068	Intermediate Similarity	NPD4368	Phase 2
0.7061	Intermediate Similarity	NPD5450	Discontinued
0.7051	Intermediate Similarity	NPD5429	Discontinued
0.7036	Intermediate Similarity	NPD5483	Clinical (unspecified phase)
0.7018	Intermediate Similarity	NPD6861	Clinical (unspecified phase)
0.7012	Intermediate Similarity	NPD6974	Phase 3
0.7004	Intermediate Similarity	NPD1505	Phase 2
0.6996	Remote Similarity	NPD7803	Approved
0.6996	Remote Similarity	NPD6160	Clinical (unspecified phase)
0.6996	Remote Similarity	NPD5083	Clinical (unspecified phase)
0.6988	Remote Similarity	NPD2951	Discontinued
0.6987	Remote Similarity	NPD4667	Clinical (unspecified phase)
0.696	Remote Similarity	NPD3006	Discontinued
0.6951	Remote Similarity	NPD3259	Approved
0.6939	Remote Similarity	NPD6247	Clinical (unspecified phase)
0.6935	Remote Similarity	NPD7956	Approved
0.6935	Remote Similarity	NPD7955	Approved
0.6933	Remote Similarity	NPD6567	Clinical (unspecified phase)
0.6914	Remote Similarity	NPD7180	Phase 3
0.6911	Remote Similarity	NPD3263	Phase 3
0.6911	Remote Similarity	NPD8370	Discontinued
0.6901	Remote Similarity	NPD4429	Discontinued
0.6898	Remote Similarity	NPD7547	Clinical (unspecified phase)
0.6894	Remote Similarity	NPD6456	Discontinued
0.689	Remote Similarity	NPD7022	Phase 2
0.688	Remote Similarity	NPD2779	Approved
0.6862	Remote Similarity	NPD4502	Phase 2
0.6858	Remote Similarity	NPD8255	Phase 2
0.6848	Remote Similarity	NPD3328	Phase 2
0.6846	Remote Similarity	NPD8463	Approved
0.6844	Remote Similarity	NPD7708	Approved
0.6844	Remote Similarity	NPD8479	Phase 2
0.6844	Remote Similarity	NPD5930	Phase 3
0.684	Remote Similarity	NPD7031	Phase 1
0.6833	Remote Similarity	NPD5866	Approved
0.6829	Remote Similarity	NPD7548	Discontinued
0.6824	Remote Similarity	NPD8117	Approved
0.6824	Remote Similarity	NPD8116	Phase 3
0.6822	Remote Similarity	NPD5102	Clinical (unspecified phase)
0.682	Remote Similarity	NPD4900	Clinical (unspecified phase)
0.6815	Remote Similarity	NPD7994	Phase 2
0.6811	Remote Similarity	NPD7025	Clinical (unspecified phase)
0.6809	Remote Similarity	NPD8359	Phase 2
0.6809	Remote Similarity	NPD8468	Phase 2
0.6805	Remote Similarity	NPD3945	Discontinued
0.6803	Remote Similarity	NPD7194	Discontinued
0.68	Remote Similarity	NPD1867	Approved
0.6793	Remote Similarity	NPD5530	Phase 1
0.6793	Remote Similarity	NPD3003	Approved
0.6789	Remote Similarity	NPD6824	Clinical (unspecified phase)
0.6786	Remote Similarity	NPD3074	Discontinued
0.6777	Remote Similarity	NPD5903	Approved
0.6777	Remote Similarity	NPD5902	Approved
0.6772	Remote Similarity	NPD4394	Clinical (unspecified phase)
0.676	Remote Similarity	NPD5479	Discontinued
0.676	Remote Similarity	NPD4898	Clinical (unspecified phase)
0.6757	Remote Similarity	NPD7013	Phase 3
0.6757	Remote Similarity	NPD8324	Phase 2
0.6757	Remote Similarity	NPD7012	Phase 3
0.6752	Remote Similarity	NPD2778	Approved
0.6751	Remote Similarity	NPD3946	Clinical (unspecified phase)
0.6747	Remote Similarity	NPD6553	Clinical (unspecified phase)
0.6747	Remote Similarity	NPD4328	Approved
0.6738	Remote Similarity	NPD6988	Phase 1
0.6736	Remote Similarity	NPD3794	Approved
0.6736	Remote Similarity	NPD7571	Clinical (unspecified phase)
0.6736	Remote Similarity	NPD3795	Approved
0.6732	Remote Similarity	NPD4958	Clinical (unspecified phase)
0.6732	Remote Similarity	NPD5805	Approved
0.6707	Remote Similarity	NPD7675	Phase 3
0.6707	Remote Similarity	NPD7676	Clinical (unspecified phase)
0.6707	Remote Similarity	NPD7674	Phase 3
0.6707	Remote Similarity	NPD5850	Phase 3
0.6694	Remote Similarity	NPD7069	Discontinued
0.6693	Remote Similarity	NPD7589	Clinical (unspecified phase)
0.6691	Remote Similarity	NPD7925	Phase 2
0.6691	Remote Similarity	NPD7924	Phase 2
0.669	Remote Similarity	NPD7690	Clinical (unspecified phase)
0.6681	Remote Similarity	NPD1768	Approved
0.6681	Remote Similarity	NPD4203	Approved
0.6681	Remote Similarity	NPD4204	Approved
0.6681	Remote Similarity	NPD7396	Approved
0.668	Remote Similarity	NPD7558	Phase 2
0.6679	Remote Similarity	NPD5922	Phase 3
0.6679	Remote Similarity	NPD7859	Phase 2
0.6667	Remote Similarity	NPD5863	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD8364	Approved
0.6667	Remote Similarity	NPD3258	Approved
0.6667	Remote Similarity	NPD8363	Approved
0.6667	Remote Similarity	NPD7467	Discontinued
0.6655	Remote Similarity	NPD7181	Phase 3
0.6654	Remote Similarity	NPD6228	Discontinued
0.6653	Remote Similarity	NPD4989	Phase 2
0.6653	Remote Similarity	NPD2285	Clinical (unspecified phase)
0.6652	Remote Similarity	NPD6590	Discontinued
0.6642	Remote Similarity	NPD8091	Phase 3
0.6642	Remote Similarity	NPD4894	Discontinued
0.6638	Remote Similarity	NPD4987	Clinical (unspecified phase)
0.6628	Remote Similarity	NPD8102	Discontinued
0.6626	Remote Similarity	NPD8109	Clinical (unspecified phase)
0.6626	Remote Similarity	NPD6985	Discontinued
0.6624	Remote Similarity	NPD7566	Clinical (unspecified phase)
0.6618	Remote Similarity	NPD8365	Clinical (unspecified phase)
0.6614	Remote Similarity	NPD6494	Phase 2
0.6612	Remote Similarity	NPD648	Clinical (unspecified phase)
0.6612	Remote Similarity	NPD1166	Clinical (unspecified phase)
0.6599	Remote Similarity	NPD6770	Approved
0.6599	Remote Similarity	NPD5519	Discontinued
0.6598	Remote Similarity	NPD6593	Clinical (unspecified phase)
0.6596	Remote Similarity	NPD5003	Discontinued
0.6591	Remote Similarity	NPD4926	Clinical (unspecified phase)
0.6586	Remote Similarity	NPD8356	Approved
0.6585	Remote Similarity	NPD8325	Phase 3
0.6585	Remote Similarity	NPD8421	Discontinued
0.6585	Remote Similarity	NPD8326	Phase 3
0.6585	Remote Similarity	NPD8327	Clinical (unspecified phase)
0.6584	Remote Similarity	NPD7468	Clinical (unspecified phase)
0.6583	Remote Similarity	NPD6245	Phase 2
0.6582	Remote Similarity	NPD8466	Approved
0.6582	Remote Similarity	NPD8467	Approved
0.6582	Remote Similarity	NPD8465	Approved
0.6581	Remote Similarity	NPD6491	Clinical (unspecified phase)
0.658	Remote Similarity	NPD1898	Discontinued
0.6579	Remote Similarity	NPD8461	Discontinued
0.6575	Remote Similarity	NPD7796	Approved
0.6575	Remote Similarity	NPD7797	Approved
0.6573	Remote Similarity	NPD3280	Approved
0.6571	Remote Similarity	NPD5293	Phase 2
0.6571	Remote Similarity	NPD1638	Discovery
0.657	Remote Similarity	NPD4506	Discontinued
0.6567	Remote Similarity	NPD4372	Phase 1
0.6564	Remote Similarity	NPD6211	Clinical (unspecified phase)
0.6561	Remote Similarity	NPD5801	Clinical (unspecified phase)
0.656	Remote Similarity	NPD3912	Discontinued
0.6556	Remote Similarity	NPD7043	Discontinued
0.6556	Remote Similarity	NPD6296	Discontinued
0.6556	Remote Similarity	NPD7222	Phase 2
0.655	Remote Similarity	NPD7885	Phase 2
0.655	Remote Similarity	NPD7886	Phase 2
0.6549	Remote Similarity	NPD6625	Approved
0.6548	Remote Similarity	NPD8430	Approved
0.6546	Remote Similarity	NPD7556	Discontinued
0.6541	Remote Similarity	NPD8244	Phase 2
0.654	Remote Similarity	NPD8101	Phase 3
0.6535	Remote Similarity	NPD1466	Phase 3
0.6535	Remote Similarity	NPD1467	Approved
0.6532	Remote Similarity	NPD3875	Discontinued
0.6532	Remote Similarity	NPD7404	Approved
0.6532	Remote Similarity	NPD2785	Clinical (unspecified phase)
0.6531	Remote Similarity	NPD2772	Clinical (unspecified phase)
0.6531	Remote Similarity	NPD2314	Clinical (unspecified phase)
0.653	Remote Similarity	NPD6530	Approved
0.653	Remote Similarity	NPD6531	Approved
0.6523	Remote Similarity	NPD6964	Approved
0.6523	Remote Similarity	NPD6963	Approved
0.652	Remote Similarity	NPD1856	Discontinued
0.6519	Remote Similarity	NPD8357	Approved
0.6518	Remote Similarity	NPD3949	Clinical (unspecified phase)
0.6516	Remote Similarity	NPD4131	Phase 3
0.6515	Remote Similarity	NPD4901	Clinical (unspecified phase)
0.6513	Remote Similarity	NPD7921	Approved
0.6513	Remote Similarity	NPD4396	Clinical (unspecified phase)
0.651	Remote Similarity	NPD4885	Approved
0.6508	Remote Similarity	NPD8289	Discontinued
0.6506	Remote Similarity	NPD3437	Discontinued
0.6504	Remote Similarity	NPD8247	Approved
0.6504	Remote Similarity	NPD3257	Approved
0.6504	Remote Similarity	NPD8246	Approved
0.6502	Remote Similarity	NPD6172	Clinical (unspecified phase)
0.6502	Remote Similarity	NPD7398	Approved
0.6502	Remote Similarity	NPD7397	Approved
0.65	Remote Similarity	NPD6517	Phase 3
0.65	Remote Similarity	NPD1483	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