NPASS Compound

Structure

CID311737 OpenBabel06191716122D 24 26 0 0 1 0 0 0 0 0999 V2000 1.7321 0.0000 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 -3.4641 2.0000 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 2.5981 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -1.0000 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 -1.7321 3.0000 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 -2.5981 0.5000 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 -2.5981 1.5000 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 -2.5981 3.5000 0.0000 C 0 0 0 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 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 -0.8660 0.5000 0.0000 C 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 -1.7321 -1.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 4.5000 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 -0.8660 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 5 1 0 0 0 0 1 11 2 0 0 0 0 2 6 2 0 0 0 0 2 11 1 0 0 0 0 3 7 1 0 0 0 0 3 12 2 0 0 0 0 4 8 2 0 0 0 0 4 12 1 0 0 0 0 5 13 2 0 0 0 0 6 13 1 0 0 0 0 7 14 2 0 0 0 0 8 14 1 0 0 0 0 9 11 1 0 0 0 0 10 12 1 0 0 0 0 13 21 1 0 0 0 0 14 22 1 0 0 0 0 15 9 1 1 0 0 0 15 17 1 0 0 0 0 15 19 1 0 0 0 0 16 10 1 1 0 0 0 16 18 1 0 0 0 0 16 20 1 0 0 0 0 17 20 2 0 0 0 0 17 23 1 0 0 0 0 18 19 2 0 0 0 0 18 24 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	326.13
Volume:	330.278
LogP:	1.318
LogD:	1.871
LogS:	-3.228
# Rotatable Bonds:	4
TPSA:	98.66
# H-Bond Aceptor:	6
# H-Bond Donor:	4
# Rings:	3
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.67
Synthetic Accessibility Score:	2.904
Fsp3:	0.222
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:	-5.204
MDCK Permeability:	3.845158062176779e-06
Pgp-inhibitor:	0.022
Pgp-substrate:	0.002
Human Intestinal Absorption (HIA):	0.843
20% Bioavailability (F20%):	0.996
30% Bioavailability (F30%):	0.911

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.028
Plasma Protein Binding (PPB):	77.98358917236328%
Volume Distribution (VD):	0.48
Pgp-substrate:	28.494380950927734%

ADMET: Metabolism

CYP1A2-inhibitor:	0.038
CYP1A2-substrate:	0.065
CYP2C19-inhibitor:	0.446
CYP2C19-substrate:	0.055
CYP2C9-inhibitor:	0.582
CYP2C9-substrate:	0.938
CYP2D6-inhibitor:	0.114
CYP2D6-substrate:	0.816
CYP3A4-inhibitor:	0.785
CYP3A4-substrate:	0.135

ADMET: Excretion

Clearance (CL):	10.678
Half-life (T1/2):	0.832

ADMET: Toxicity

hERG Blockers:	0.178
Human Hepatotoxicity (H-HT):	0.34
Drug-inuced Liver Injury (DILI):	0.049
AMES Toxicity:	0.321
Rat Oral Acute Toxicity:	0.389
Maximum Recommended Daily Dose:	0.36
Skin Sensitization:	0.319
Carcinogencity:	0.449
Eye Corrosion:	0.003
Eye Irritation:	0.011
Respiratory Toxicity:	0.028

Download Data

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

Natural Product: NPC311737

Natural Product ID:	NPC311737
*Common Name:**	Cyclo(-Trp-Tyr)
IUPAC Name:	(3S,6S)-3,6-bis[(4-hydroxyphenyl)methyl]piperazine-2,5-dione
Synonyms:	Cyclo(-Trp-Tyr)
Standard InCHIKey:	NGPCLOGFGKJCBP-HOTGVXAUSA-N
Standard InCHI:	InChI=1S/C18H18N2O4/c21-13-5-1-11(2-6-13)9-15-17(23)20-16(18(24)19-15)10-12-3-7-14(22)8-4-12/h1-8,15-16,21-22H,9-10H2,(H,19,24)(H,20,23)/t15-,16-/m0/s1
SMILES:	OC1=N[C@@H](Cc2ccc(cc2)O)C(=N[C@H]1Cc1ccc(cc1)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL189558
PubChem CID:	11267350
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
NPO30270	Cordyceps sinensis	Species	Cordycipitaceae	Eukaryota	n.a.	mycelium	n.a.	PMID[10423860]
NPO30270	Cordyceps sinensis	Species	Cordycipitaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15863936]
NPO30270	Cordyceps sinensis	Species	Cordycipitaceae	Eukaryota	n.a.	mycelium	n.a.	PMID[21848266]
NPO30270	Cordyceps sinensis	Species	Cordycipitaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21848266]
NPO30270	Cordyceps sinensis	Species	Cordycipitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO30270	Cordyceps sinensis	Species	Cordycipitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]

☑ 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
Kd	2
MIC	5
Others	7

Activity Type	# Activity
Individual Protein	1
Organism	7
Others	3
SINGLE PROTEIN	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT3579	Individual Protein	Calpain 1	Homo sapiens	Inhibition	=	0.0	%	PMID[494917]
NPT27	Others	Unspecified		LogP app	=	-6.17	n.a.	PMID[494918]
NPT35	Others	n.a.		LogP	=	1.11	n.a.	PMID[494918]
NPT2	Others	Unspecified		Kd	=	5820.0	nM	PMID[494919]
NPT26232	SINGLE PROTEIN	Cytochrome P450	Mycobacterium tuberculosis	Kd	=	30000.0	nM	PMID[494920]
NPT26232	SINGLE PROTEIN	Cytochrome P450	Mycobacterium tuberculosis	Activity	=	52.0	%	PMID[494920]
NPT26232	SINGLE PROTEIN	Cytochrome P450	Mycobacterium tuberculosis	Activity	=	2.7	%	PMID[494920]
NPT878	Organism	Streptococcus mutans	Streptococcus mutans	MIC	=	96.0	ug.mL-1	PMID[494921]
NPT878	Organism	Streptococcus mutans	Streptococcus mutans	MBC	>	192.0	ug ml-1	PMID[494921]
NPT19	Organism	Escherichia coli	Escherichia coli	MIC	>	192.0	ug.mL-1	PMID[494921]
NPT18	Organism	Pseudomonas aeruginosa	Pseudomonas aeruginosa	MIC	>	192.0	ug.mL-1	PMID[494921]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	>	192.0	ug.mL-1	PMID[494921]
NPT564	Organism	Listeria monocytogenes	Listeria monocytogenes	MIC	>	192.0	ug.mL-1	PMID[494921]
NPT20	Organism	Candida albicans	Candida albicans	Activity	=	20.0	%	PMID[494921]

☑ 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 NPC311737 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	204
0.1-0.2	1993
0.2-0.3	9981
0.3-0.4	7805
0.4-0.5	10989
0.5-0.6	9060
0.6-0.7	2248
0.7-0.8	376
0.8-0.85	22
0.85-0.9	15
0.9-0.95	1
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC38458
0.9908	High Similarity	NPC82963
0.9369	High Similarity	NPC118202
0.9115	High Similarity	NPC317254
0.9	High Similarity	NPC24101
0.9	High Similarity	NPC96224
0.8829	High Similarity	NPC153690
0.8818	High Similarity	NPC231705
0.8803	High Similarity	NPC283760
0.875	High Similarity	NPC258056
0.8673	High Similarity	NPC474149
0.8644	High Similarity	NPC268572
0.8571	High Similarity	NPC142297
0.8548	High Similarity	NPC325651
0.8545	High Similarity	NPC178902
0.8492	Intermediate Similarity	NPC244866
0.8413	Intermediate Similarity	NPC326966
0.8403	Intermediate Similarity	NPC122009
0.8319	Intermediate Similarity	NPC283468
0.8281	Intermediate Similarity	NPC267237
0.8279	Intermediate Similarity	NPC474862
0.8257	Intermediate Similarity	NPC311242
0.8189	Intermediate Similarity	NPC474091
0.8182	Intermediate Similarity	NPC43275
0.8182	Intermediate Similarity	NPC319950
0.813	Intermediate Similarity	NPC27581
0.807	Intermediate Similarity	NPC211551
0.8049	Intermediate Similarity	NPC284078
0.803	Intermediate Similarity	NPC214988
0.8018	Intermediate Similarity	NPC107619
0.8	Intermediate Similarity	NPC307020
0.7984	Intermediate Similarity	NPC45191
0.7984	Intermediate Similarity	NPC475735
0.797	Intermediate Similarity	NPC476989
0.7969	Intermediate Similarity	NPC478147
0.7937	Intermediate Similarity	NPC95733
0.7937	Intermediate Similarity	NPC62101
0.7928	Intermediate Similarity	NPC33168
0.7917	Intermediate Similarity	NPC142599
0.791	Intermediate Similarity	NPC168861
0.7909	Intermediate Similarity	NPC151715
0.7891	Intermediate Similarity	NPC296712
0.7891	Intermediate Similarity	NPC477839
0.7879	Intermediate Similarity	NPC6913
0.7876	Intermediate Similarity	NPC289381
0.7876	Intermediate Similarity	NPC155847
0.7874	Intermediate Similarity	NPC29477
0.7857	Intermediate Similarity	NPC211218
0.7851	Intermediate Similarity	NPC37302
0.7846	Intermediate Similarity	NPC114102
0.7846	Intermediate Similarity	NPC473724
0.784	Intermediate Similarity	NPC142577
0.7838	Intermediate Similarity	NPC26244
0.7829	Intermediate Similarity	NPC271808
0.7823	Intermediate Similarity	NPC263835
0.782	Intermediate Similarity	NPC313694
0.782	Intermediate Similarity	NPC242159
0.7798	Intermediate Similarity	NPC226438
0.7788	Intermediate Similarity	NPC125732
0.7768	Intermediate Similarity	NPC473388
0.7752	Intermediate Similarity	NPC251571
0.7748	Intermediate Similarity	NPC161972
0.7748	Intermediate Similarity	NPC303045
0.7744	Intermediate Similarity	NPC64205
0.7744	Intermediate Similarity	NPC6570
0.7727	Intermediate Similarity	NPC45040
0.771	Intermediate Similarity	NPC257390
0.7706	Intermediate Similarity	NPC172128
0.7681	Intermediate Similarity	NPC16188
0.7674	Intermediate Similarity	NPC476353
0.7652	Intermediate Similarity	NPC7686
0.7652	Intermediate Similarity	NPC40258
0.7652	Intermediate Similarity	NPC471953
0.7652	Intermediate Similarity	NPC91461
0.7652	Intermediate Similarity	NPC214869
0.7647	Intermediate Similarity	NPC83289
0.7647	Intermediate Similarity	NPC290566
0.7647	Intermediate Similarity	NPC189724
0.7647	Intermediate Similarity	NPC212850
0.7647	Intermediate Similarity	NPC145638
0.7638	Intermediate Similarity	NPC471314
0.7638	Intermediate Similarity	NPC471315
0.7634	Intermediate Similarity	NPC52029
0.7634	Intermediate Similarity	NPC195749
0.7634	Intermediate Similarity	NPC35961
0.7632	Intermediate Similarity	NPC78119
0.7632	Intermediate Similarity	NPC132078
0.7632	Intermediate Similarity	NPC216468
0.7632	Intermediate Similarity	NPC51333
0.7611	Intermediate Similarity	NPC292730
0.7611	Intermediate Similarity	NPC132271
0.7611	Intermediate Similarity	NPC82664
0.7611	Intermediate Similarity	NPC216520
0.7597	Intermediate Similarity	NPC476249
0.7591	Intermediate Similarity	NPC474128
0.7589	Intermediate Similarity	NPC128062
0.7589	Intermediate Similarity	NPC233702
0.7574	Intermediate Similarity	NPC197921
0.7571	Intermediate Similarity	NPC245974
0.7565	Intermediate Similarity	NPC213730
0.7561	Intermediate Similarity	NPC303370
0.7557	Intermediate Similarity	NPC155838
0.7554	Intermediate Similarity	NPC247298
0.7545	Intermediate Similarity	NPC280347
0.7545	Intermediate Similarity	NPC177420
0.7541	Intermediate Similarity	NPC474544
0.7541	Intermediate Similarity	NPC1986
0.754	Intermediate Similarity	NPC41801
0.754	Intermediate Similarity	NPC252817
0.7538	Intermediate Similarity	NPC301713
0.7537	Intermediate Similarity	NPC120114
0.7537	Intermediate Similarity	NPC71888
0.7522	Intermediate Similarity	NPC274678
0.7522	Intermediate Similarity	NPC25565
0.7521	Intermediate Similarity	NPC227553
0.7521	Intermediate Similarity	NPC163674
0.7521	Intermediate Similarity	NPC166837
0.7519	Intermediate Similarity	NPC328070
0.7518	Intermediate Similarity	NPC469360
0.7518	Intermediate Similarity	NPC91953
0.7518	Intermediate Similarity	NPC473491
0.75	Intermediate Similarity	NPC160607
0.75	Intermediate Similarity	NPC204848
0.75	Intermediate Similarity	NPC258992
0.75	Intermediate Similarity	NPC106551
0.75	Intermediate Similarity	NPC48202
0.75	Intermediate Similarity	NPC188867
0.75	Intermediate Similarity	NPC281686
0.75	Intermediate Similarity	NPC14600
0.75	Intermediate Similarity	NPC312770
0.75	Intermediate Similarity	NPC41473
0.7481	Intermediate Similarity	NPC186898
0.748	Intermediate Similarity	NPC83279
0.7478	Intermediate Similarity	NPC130193
0.7478	Intermediate Similarity	NPC92730
0.7477	Intermediate Similarity	NPC55561
0.7456	Intermediate Similarity	NPC475439
0.7456	Intermediate Similarity	NPC473501
0.7455	Intermediate Similarity	NPC113460
0.7455	Intermediate Similarity	NPC25493
0.7447	Intermediate Similarity	NPC132771
0.7445	Intermediate Similarity	NPC299583
0.7436	Intermediate Similarity	NPC68055
0.7436	Intermediate Similarity	NPC168829
0.7436	Intermediate Similarity	NPC135784
0.7434	Intermediate Similarity	NPC76938
0.7426	Intermediate Similarity	NPC473055
0.7426	Intermediate Similarity	NPC309667
0.7426	Intermediate Similarity	NPC473052
0.7419	Intermediate Similarity	NPC10286
0.7419	Intermediate Similarity	NPC213
0.7414	Intermediate Similarity	NPC29601
0.7413	Intermediate Similarity	NPC202198
0.741	Intermediate Similarity	NPC266741
0.7402	Intermediate Similarity	NPC17388
0.7402	Intermediate Similarity	NPC289330
0.7402	Intermediate Similarity	NPC160120
0.7402	Intermediate Similarity	NPC471308
0.7402	Intermediate Similarity	NPC53596
0.7398	Intermediate Similarity	NPC309808
0.7395	Intermediate Similarity	NPC188677
0.7395	Intermediate Similarity	NPC70843
0.7391	Intermediate Similarity	NPC225464
0.7391	Intermediate Similarity	NPC201967
0.7388	Intermediate Similarity	NPC470392
0.7387	Intermediate Similarity	NPC318325
0.7387	Intermediate Similarity	NPC123273
0.7387	Intermediate Similarity	NPC242240
0.7385	Intermediate Similarity	NPC4974
0.7376	Intermediate Similarity	NPC5462
0.7373	Intermediate Similarity	NPC120693
0.7373	Intermediate Similarity	NPC288411
0.7373	Intermediate Similarity	NPC261573
0.7373	Intermediate Similarity	NPC8931
0.7372	Intermediate Similarity	NPC471201
0.7372	Intermediate Similarity	NPC322526
0.7372	Intermediate Similarity	NPC193528
0.7368	Intermediate Similarity	NPC32714
0.7368	Intermediate Similarity	NPC259665
0.7368	Intermediate Similarity	NPC126859
0.7368	Intermediate Similarity	NPC89769
0.7364	Intermediate Similarity	NPC23167
0.7357	Intermediate Similarity	NPC81026
0.7355	Intermediate Similarity	NPC265211
0.7355	Intermediate Similarity	NPC306045
0.7348	Intermediate Similarity	NPC268763
0.7348	Intermediate Similarity	NPC153990
0.7348	Intermediate Similarity	NPC66177
0.7348	Intermediate Similarity	NPC8305
0.7344	Intermediate Similarity	NPC324702
0.7339	Intermediate Similarity	NPC175313
0.7338	Intermediate Similarity	NPC326241
0.7329	Intermediate Similarity	NPC56635
0.7323	Intermediate Similarity	NPC256369
0.7323	Intermediate Similarity	NPC239697
0.7321	Intermediate Similarity	NPC300017
0.7317	Intermediate Similarity	NPC146422
0.7311	Intermediate Similarity	NPC474839
0.7311	Intermediate Similarity	NPC154899
0.7311	Intermediate Similarity	NPC233396

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 NPC311737 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	136
0.1-0.2	651
0.2-0.3	1050
0.3-0.4	1647
0.4-0.5	2971
0.5-0.6	1971
0.6-0.7	620
0.7-0.8	101
0.8-0.85	2
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8843	High Similarity	NPD7451	Discontinued
0.8145	Intermediate Similarity	NPD3676	Clinical (unspecified phase)
0.8106	Intermediate Similarity	NPD7450	Phase 2
0.8049	Intermediate Similarity	NPD3421	Phase 3
0.8047	Intermediate Similarity	NPD3136	Phase 2
0.803	Intermediate Similarity	NPD6866	Clinical (unspecified phase)
0.803	Intermediate Similarity	NPD6867	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD4659	Approved
0.7983	Intermediate Similarity	NPD2229	Approved
0.7983	Intermediate Similarity	NPD2228	Approved
0.7983	Intermediate Similarity	NPD2234	Approved
0.7982	Intermediate Similarity	NPD9610	Approved
0.7982	Intermediate Similarity	NPD9608	Approved
0.7923	Intermediate Similarity	NPD5729	Clinical (unspecified phase)
0.792	Intermediate Similarity	NPD2562	Approved
0.792	Intermediate Similarity	NPD2561	Approved
0.791	Intermediate Similarity	NPD6809	Clinical (unspecified phase)
0.7909	Intermediate Similarity	NPD2933	Approved
0.7909	Intermediate Similarity	NPD2934	Approved
0.7874	Intermediate Similarity	NPD4104	Clinical (unspecified phase)
0.7874	Intermediate Similarity	NPD4103	Phase 2
0.7838	Intermediate Similarity	NPD2860	Approved
0.7838	Intermediate Similarity	NPD2859	Approved
0.7805	Intermediate Similarity	NPD5303	Approved
0.7805	Intermediate Similarity	NPD5304	Approved
0.7778	Intermediate Similarity	NPD2337	Clinical (unspecified phase)
0.7742	Intermediate Similarity	NPD4093	Discontinued
0.7737	Intermediate Similarity	NPD7066	Clinical (unspecified phase)
0.7727	Intermediate Similarity	NPD6346	Approved
0.7687	Intermediate Similarity	NPD3552	Approved
0.7687	Intermediate Similarity	NPD3553	Approved
0.7687	Intermediate Similarity	NPD3554	Approved
0.7687	Intermediate Similarity	NPD3555	Approved
0.768	Intermediate Similarity	NPD5238	Clinical (unspecified phase)
0.7647	Intermediate Similarity	NPD9380	Clinical (unspecified phase)
0.7632	Intermediate Similarity	NPD3020	Approved
0.7597	Intermediate Similarity	NPD3053	Approved
0.7597	Intermediate Similarity	NPD3055	Approved
0.7581	Intermediate Similarity	NPD318	Approved
0.7581	Intermediate Similarity	NPD317	Approved
0.752	Intermediate Similarity	NPD1759	Phase 1
0.752	Intermediate Similarity	NPD2226	Clinical (unspecified phase)
0.7519	Intermediate Similarity	NPD5311	Approved
0.7519	Intermediate Similarity	NPD5310	Approved
0.7519	Intermediate Similarity	NPD7477	Discontinued
0.7518	Intermediate Similarity	NPD7978	Discontinued
0.75	Intermediate Similarity	NPD1792	Phase 2
0.75	Intermediate Similarity	NPD2372	Approved
0.75	Intermediate Similarity	NPD9568	Approved
0.7481	Intermediate Similarity	NPD4993	Discontinued
0.7465	Intermediate Similarity	NPD7303	Discontinued
0.7464	Intermediate Similarity	NPD7596	Clinical (unspecified phase)
0.7442	Intermediate Similarity	NPD1669	Approved
0.744	Intermediate Similarity	NPD856	Approved
0.744	Intermediate Similarity	NPD1758	Phase 1
0.744	Intermediate Similarity	NPD16	Approved
0.7395	Intermediate Similarity	NPD1445	Approved
0.7395	Intermediate Similarity	NPD1444	Approved
0.7368	Intermediate Similarity	NPD5155	Approved
0.7368	Intermediate Similarity	NPD5156	Approved
0.7357	Intermediate Similarity	NPD3400	Discontinued
0.7353	Intermediate Similarity	NPD2568	Approved
0.7348	Intermediate Similarity	NPD3637	Approved
0.7348	Intermediate Similarity	NPD3635	Approved
0.7348	Intermediate Similarity	NPD3636	Approved
0.7339	Intermediate Similarity	NPD9614	Approved
0.7339	Intermediate Similarity	NPD9618	Approved
0.7317	Intermediate Similarity	NPD9379	Approved
0.7317	Intermediate Similarity	NPD9377	Approved
0.7308	Intermediate Similarity	NPD6583	Phase 3
0.7308	Intermediate Similarity	NPD6582	Phase 2
0.7293	Intermediate Similarity	NPD3595	Approved
0.7293	Intermediate Similarity	NPD2606	Approved
0.7293	Intermediate Similarity	NPD3594	Approved
0.7293	Intermediate Similarity	NPD2605	Approved
0.7279	Intermediate Similarity	NPD8019	Approved
0.7266	Intermediate Similarity	NPD2667	Approved
0.7266	Intermediate Similarity	NPD2668	Approved
0.7265	Intermediate Similarity	NPD4760	Clinical (unspecified phase)
0.7259	Intermediate Similarity	NPD2674	Phase 3
0.7259	Intermediate Similarity	NPD6407	Approved
0.7259	Intermediate Similarity	NPD6405	Approved
0.7254	Intermediate Similarity	NPD7554	Discontinued
0.7234	Intermediate Similarity	NPD6331	Phase 2
0.7231	Intermediate Similarity	NPD5108	Clinical (unspecified phase)
0.7227	Intermediate Similarity	NPD179	Clinical (unspecified phase)
0.7226	Intermediate Similarity	NPD5314	Approved
0.7226	Intermediate Similarity	NPD3052	Approved
0.7226	Intermediate Similarity	NPD3054	Approved
0.7213	Intermediate Similarity	NPD3021	Approved
0.7213	Intermediate Similarity	NPD3022	Approved
0.7209	Intermediate Similarity	NPD1981	Approved
0.7209	Intermediate Similarity	NPD1983	Approved
0.7209	Intermediate Similarity	NPD1980	Approved
0.7206	Intermediate Similarity	NPD3062	Approved
0.7206	Intermediate Similarity	NPD3061	Approved
0.7206	Intermediate Similarity	NPD3059	Approved
0.7203	Intermediate Similarity	NPD6682	Clinical (unspecified phase)
0.719	Intermediate Similarity	NPD6038	Clinical (unspecified phase)
0.7163	Intermediate Similarity	NPD2459	Approved
0.7163	Intermediate Similarity	NPD2458	Approved
0.7163	Intermediate Similarity	NPD2460	Phase 3
0.7162	Intermediate Similarity	NPD7495	Discontinued
0.7154	Intermediate Similarity	NPD5350	Clinical (unspecified phase)
0.7154	Intermediate Similarity	NPD5351	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD2194	Approved
0.7143	Intermediate Similarity	NPD4656	Approved
0.7143	Intermediate Similarity	NPD4658	Approved
0.7143	Intermediate Similarity	NPD255	Approved
0.7143	Intermediate Similarity	NPD6584	Phase 3
0.7143	Intermediate Similarity	NPD256	Approved
0.7143	Intermediate Similarity	NPD2195	Approved
0.7132	Intermediate Similarity	NPD1751	Approved
0.713	Intermediate Similarity	NPD1432	Clinical (unspecified phase)
0.7119	Intermediate Similarity	NPD3028	Approved
0.7113	Intermediate Similarity	NPD6658	Clinical (unspecified phase)
0.7105	Intermediate Similarity	NPD6690	Approved
0.7105	Intermediate Similarity	NPD1814	Approved
0.7105	Intermediate Similarity	NPD1812	Approved
0.7095	Intermediate Similarity	NPD7438	Suspended
0.7094	Intermediate Similarity	NPD9273	Approved
0.7091	Intermediate Similarity	NPD111	Approved
0.7087	Intermediate Similarity	NPD7325	Clinical (unspecified phase)
0.7077	Intermediate Similarity	NPD3143	Discontinued
0.7075	Intermediate Similarity	NPD4005	Discontinued
0.7068	Intermediate Similarity	NPD1133	Approved
0.7068	Intermediate Similarity	NPD1135	Approved
0.7068	Intermediate Similarity	NPD1131	Approved
0.7068	Intermediate Similarity	NPD1134	Approved
0.7068	Intermediate Similarity	NPD1129	Approved
0.7063	Intermediate Similarity	NPD1791	Approved
0.7063	Intermediate Similarity	NPD1793	Approved
0.7059	Intermediate Similarity	NPD854	Approved
0.7059	Intermediate Similarity	NPD8011	Discontinued
0.7059	Intermediate Similarity	NPD855	Approved
0.7059	Intermediate Similarity	NPD3056	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD3145	Approved
0.7059	Intermediate Similarity	NPD3144	Approved
0.7059	Intermediate Similarity	NPD2028	Clinical (unspecified phase)
0.7055	Intermediate Similarity	NPD7523	Phase 3
0.7055	Intermediate Similarity	NPD7131	Phase 3
0.7049	Intermediate Similarity	NPD4095	Clinical (unspecified phase)
0.7045	Intermediate Similarity	NPD9622	Approved
0.704	Intermediate Similarity	NPD821	Approved
0.7034	Intermediate Similarity	NPD2874	Phase 2
0.7031	Intermediate Similarity	NPD9615	Approved
0.7031	Intermediate Similarity	NPD9616	Approved
0.7031	Intermediate Similarity	NPD9613	Approved
0.7025	Intermediate Similarity	NPD999	Phase 2
0.7021	Intermediate Similarity	NPD4721	Approved
0.7021	Intermediate Similarity	NPD4725	Approved
0.7021	Intermediate Similarity	NPD4726	Approved
0.7016	Intermediate Similarity	NPD4254	Approved
0.7016	Intermediate Similarity	NPD4253	Approved
0.7009	Intermediate Similarity	NPD1875	Phase 1
0.7007	Intermediate Similarity	NPD840	Approved
0.7007	Intermediate Similarity	NPD839	Approved
0.7	Intermediate Similarity	NPD1753	Discontinued
0.7	Intermediate Similarity	NPD9384	Approved
0.7	Intermediate Similarity	NPD9381	Approved
0.7	Intermediate Similarity	NPD4231	Approved
0.7	Intermediate Similarity	NPD4229	Approved
0.6985	Remote Similarity	NPD1024	Discontinued
0.6978	Remote Similarity	NPD1772	Clinical (unspecified phase)
0.6977	Remote Similarity	NPD316	Approved
0.6975	Remote Similarity	NPD1242	Phase 1
0.6963	Remote Similarity	NPD9569	Approved
0.6957	Remote Similarity	NPD5837	Clinical (unspecified phase)
0.6953	Remote Similarity	NPD6775	Clinical (unspecified phase)
0.6949	Remote Similarity	NPD9612	Approved
0.6949	Remote Similarity	NPD9611	Approved
0.6949	Remote Similarity	NPD9609	Approved
0.6934	Remote Similarity	NPD601	Approved
0.6934	Remote Similarity	NPD597	Approved
0.6934	Remote Similarity	NPD598	Approved
0.6929	Remote Similarity	NPD475	Phase 2
0.6918	Remote Similarity	NPD5348	Clinical (unspecified phase)
0.6918	Remote Similarity	NPD3985	Discontinued
0.6918	Remote Similarity	NPD4123	Phase 3
0.6918	Remote Similarity	NPD4739	Approved
0.6917	Remote Similarity	NPD3685	Discontinued
0.6917	Remote Similarity	NPD4817	Approved
0.6917	Remote Similarity	NPD846	Approved
0.6917	Remote Similarity	NPD4818	Approved
0.6917	Remote Similarity	NPD940	Approved
0.6885	Remote Similarity	NPD5717	Approved
0.6884	Remote Similarity	NPD1132	Approved
0.6884	Remote Similarity	NPD1136	Approved
0.6884	Remote Similarity	NPD5745	Approved
0.6884	Remote Similarity	NPD1130	Approved
0.6884	Remote Similarity	NPD1423	Approved
0.688	Remote Similarity	NPD9280	Clinical (unspecified phase)
0.688	Remote Similarity	NPD4025	Clinical (unspecified phase)
0.6879	Remote Similarity	NPD4108	Discontinued
0.6875	Remote Similarity	NPD5481	Discontinued
0.6871	Remote Similarity	NPD6390	Discontinued
0.687	Remote Similarity	NPD2286	Discontinued
0.6867	Remote Similarity	NPD7118	Clinical (unspecified phase)
0.6867	Remote Similarity	NPD6072	Discontinued
0.6867	Remote Similarity	NPD3778	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