NPASS Compound

Structure

CID311242 OpenBabel06191716122D 22 24 0 0 1 0 0 0 0 0999 V2000 -0.8660 4.5000 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 -0.0000 4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 -0.0000 0.0000 C 0 0 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 -0.0000 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 4.3301 -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 -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 -0.8660 2.5000 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 -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 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 3 2 0 0 0 0 1 4 1 0 0 0 0 2 5 2 0 0 0 0 2 6 1 0 0 0 0 3 7 1 0 0 0 0 4 8 2 0 0 0 0 5 9 1 0 0 0 0 6 10 2 0 0 0 0 7 13 2 0 0 0 0 8 13 1 0 0 0 0 9 14 2 0 0 0 0 10 14 1 0 0 0 0 11 13 1 0 0 0 0 12 14 1 0 0 0 0 15 11 1 1 0 0 0 15 17 1 0 0 0 0 15 19 1 0 0 0 0 16 12 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 21 1 0 0 0 0 18 19 2 0 0 0 0 18 22 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	294.14
Volume:	312.697
LogP:	2.523
LogD:	3.1
LogS:	-3.362
# Rotatable Bonds:	4
TPSA:	58.2
# H-Bond Aceptor:	4
# H-Bond Donor:	2
# Rings:	3
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.897
Synthetic Accessibility Score:	2.61
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:	-4.783
MDCK Permeability:	0.0001352037797914818
Pgp-inhibitor:	0.008
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.844
20% Bioavailability (F20%):	0.994
30% Bioavailability (F30%):	0.178

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.145
Plasma Protein Binding (PPB):	93.68856048583984%
Volume Distribution (VD):	0.655
Pgp-substrate:	9.01041030883789%

ADMET: Metabolism

CYP1A2-inhibitor:	0.142
CYP1A2-substrate:	0.082
CYP2C19-inhibitor:	0.828
CYP2C19-substrate:	0.097
CYP2C9-inhibitor:	0.646
CYP2C9-substrate:	0.321
CYP2D6-inhibitor:	0.144
CYP2D6-substrate:	0.52
CYP3A4-inhibitor:	0.794
CYP3A4-substrate:	0.344

ADMET: Excretion

Clearance (CL):	3.544
Half-life (T1/2):	0.651

ADMET: Toxicity

hERG Blockers:	0.125
Human Hepatotoxicity (H-HT):	0.445
Drug-inuced Liver Injury (DILI):	0.284
AMES Toxicity:	0.681
Rat Oral Acute Toxicity:	0.663
Maximum Recommended Daily Dose:	0.342
Skin Sensitization:	0.111
Carcinogencity:	0.218
Eye Corrosion:	0.003
Eye Irritation:	0.012
Respiratory Toxicity:	0.033

Download Data

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

Natural Product: NPC311242

Natural Product ID:	NPC311242
*Common Name:**	(3S,6S)-3,6-Dibenzylpiperazine-2,5-Dione
IUPAC Name:	(3S,6S)-3,6-dibenzylpiperazine-2,5-dione
Synonyms:
Standard InCHIKey:	JUAPMRSLDANLAS-HOTGVXAUSA-N
Standard InCHI:	InChI=1S/C18H18N2O2/c21-17-15(11-13-7-3-1-4-8-13)19-18(22)16(20-17)12-14-9-5-2-6-10-14/h1-10,15-16H,11-12H2,(H,19,22)(H,20,21)/t15-,16-/m0/s1
SMILES:	OC1=N[C@@H](Cc2ccccc2)C(=N[C@H]1Cc1ccccc1)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL126124
PubChem CID:	76116
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0002279] Benzene and substituted 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
NPO18557	Epicoccum nigrum	Species	Didymellaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17711348]
NPO18557	Epicoccum nigrum	Species	Didymellaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19919067]
NPO18557	Epicoccum nigrum	Species	Didymellaceae	Eukaryota	n.a.	The fungus is isolated from the leaves of L. rhodostegia, collected in June 2007 at Nanning, Guangxi Province, China	2007-JUN	PMID[20550196]
NPO28219	Euphorbia peplus	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21612217]
NPO18557	Epicoccum nigrum	Species	Didymellaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24328302]
NPO28219	Euphorbia peplus	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[27203291]
NPO18557	Epicoccum nigrum	Species	Didymellaceae	Eukaryota	n.a.	n.a.	n.a.	Database[Title]
NPO28129	Reticulitermes virginicus	Species	Termitoidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23676	Fleroya rubrostipulata	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28219	Euphorbia peplus	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18557	Epicoccum nigrum	Species	Didymellaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28114	Peltophorum adnatum	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23882	Cremastosperma microcarpum	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27974	Swertia leduci	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28310	Phacelocarpus labillardieri	Species	Phacelocarpaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28982	Calliandra confusa	Species	Fabaceae	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
IC50	1
Kd	1
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[505675]
NPT35	Others	n.a.		LogP	=	1.59	n.a.	PMID[505674]
NPT27	Others	Unspecified		Log Phep	<	3.0	n.a.	PMID[505674]
NPT35	Others	n.a.		LogP	=	2.86	n.a.	PMID[505674]
NPT474	Organism	Plasmodium berghei	Plasmodium berghei	Activity	=	84.33	%	PMID[505677]
NPT474	Organism	Plasmodium berghei	Plasmodium berghei	IC50	=	2540.0	nM	PMID[505677]
NPT26232	SINGLE PROTEIN	Cytochrome P450	Mycobacterium tuberculosis	Kd	=	2400.0	nM	PMID[505678]
NPT26232	SINGLE PROTEIN	Cytochrome P450	Mycobacterium tuberculosis	Activity	=	3.0	%	PMID[505678]
NPT26232	SINGLE PROTEIN	Cytochrome P450	Mycobacterium tuberculosis	Activity	=	0.0	%	PMID[505678]
NPT88	Organism	Mycobacterium tuberculosis	Mycobacterium tuberculosis	MIC	>	100000.0	nM	PMID[505678]
NPT19	Organism	Escherichia coli	Escherichia coli	MIC	>	192.0	ug.mL-1	PMID[505679]
NPT18	Organism	Pseudomonas aeruginosa	Pseudomonas aeruginosa	MIC	>	192.0	ug.mL-1	PMID[505679]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	>	192.0	ug.mL-1	PMID[505679]
NPT564	Organism	Listeria monocytogenes	Listeria monocytogenes	MIC	>	192.0	ug.mL-1	PMID[505679]

☑ 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 NPC311242 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	125
0.1-0.2	1589
0.2-0.3	10336
0.3-0.4	16418
0.4-0.5	10986
0.5-0.6	2645
0.6-0.7	444
0.7-0.8	123
0.8-0.85	24
0.85-0.9	3
0.9-0.95	2
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9444	High Similarity	NPC226438
0.9348	High Similarity	NPC161972
0.9348	High Similarity	NPC303045
0.8913	High Similarity	NPC172128
0.8842	High Similarity	NPC25565
0.875	High Similarity	NPC473501
0.875	High Similarity	NPC475439
0.8404	Intermediate Similarity	NPC470877
0.8387	Intermediate Similarity	NPC471638
0.8333	Intermediate Similarity	NPC211551
0.8333	Intermediate Similarity	NPC82963
0.8316	Intermediate Similarity	NPC159178
0.8316	Intermediate Similarity	NPC78041
0.8316	Intermediate Similarity	NPC209764
0.8316	Intermediate Similarity	NPC471307
0.8316	Intermediate Similarity	NPC141139
0.8316	Intermediate Similarity	NPC74936
0.8316	Intermediate Similarity	NPC121872
0.8316	Intermediate Similarity	NPC316108
0.8286	Intermediate Similarity	NPC319579
0.8257	Intermediate Similarity	NPC311737
0.8257	Intermediate Similarity	NPC38458
0.8235	Intermediate Similarity	NPC194390
0.8235	Intermediate Similarity	NPC88267
0.8235	Intermediate Similarity	NPC224610
0.8235	Intermediate Similarity	NPC113326
0.8182	Intermediate Similarity	NPC33168
0.8163	Intermediate Similarity	NPC58674
0.8085	Intermediate Similarity	NPC203076
0.8061	Intermediate Similarity	NPC471309
0.7982	Intermediate Similarity	NPC33742
0.7917	Intermediate Similarity	NPC325441
0.7917	Intermediate Similarity	NPC12429
0.7905	Intermediate Similarity	NPC327481
0.7857	Intermediate Similarity	NPC245259
0.7843	Intermediate Similarity	NPC12730
0.7838	Intermediate Similarity	NPC470544
0.7818	Intermediate Similarity	NPC118202
0.7788	Intermediate Similarity	NPC164859
0.7768	Intermediate Similarity	NPC470545
0.7755	Intermediate Similarity	NPC258627
0.7732	Intermediate Similarity	NPC262393
0.7699	Intermediate Similarity	NPC470546
0.7636	Intermediate Similarity	NPC474584
0.7619	Intermediate Similarity	NPC471317
0.7568	Intermediate Similarity	NPC276949
0.7568	Intermediate Similarity	NPC35850
0.7565	Intermediate Similarity	NPC477061
0.7565	Intermediate Similarity	NPC45777
0.7545	Intermediate Similarity	NPC329011
0.75	Intermediate Similarity	NPC71684
0.7453	Intermediate Similarity	NPC471310
0.7453	Intermediate Similarity	NPC202613
0.7449	Intermediate Similarity	NPC473031
0.7447	Intermediate Similarity	NPC192623
0.7434	Intermediate Similarity	NPC317254
0.7431	Intermediate Similarity	NPC24101
0.7431	Intermediate Similarity	NPC96224
0.7429	Intermediate Similarity	NPC469457
0.7423	Intermediate Similarity	NPC3210
0.7411	Intermediate Similarity	NPC1986
0.7411	Intermediate Similarity	NPC474544
0.7395	Intermediate Similarity	NPC4974
0.7373	Intermediate Similarity	NPC35996
0.7368	Intermediate Similarity	NPC315276
0.7368	Intermediate Similarity	NPC285926
0.7368	Intermediate Similarity	NPC14672
0.7304	Intermediate Similarity	NPC169328
0.7304	Intermediate Similarity	NPC254088
0.7292	Intermediate Similarity	NPC14326
0.7281	Intermediate Similarity	NPC197470
0.7273	Intermediate Similarity	NPC153690
0.7255	Intermediate Similarity	NPC265521
0.725	Intermediate Similarity	NPC47667
0.7248	Intermediate Similarity	NPC231705
0.7241	Intermediate Similarity	NPC310467
0.7241	Intermediate Similarity	NPC314992
0.7241	Intermediate Similarity	NPC237420
0.7217	Intermediate Similarity	NPC2265
0.7213	Intermediate Similarity	NPC473322
0.7213	Intermediate Similarity	NPC111428
0.7207	Intermediate Similarity	NPC292758
0.7207	Intermediate Similarity	NPC258056
0.7207	Intermediate Similarity	NPC65855
0.719	Intermediate Similarity	NPC477937
0.7179	Intermediate Similarity	NPC283760
0.7143	Intermediate Similarity	NPC474149
0.7143	Intermediate Similarity	NPC10781
0.7143	Intermediate Similarity	NPC293628
0.7143	Intermediate Similarity	NPC122493
0.7131	Intermediate Similarity	NPC210950
0.7131	Intermediate Similarity	NPC199738
0.7119	Intermediate Similarity	NPC478014
0.7119	Intermediate Similarity	NPC478016
0.7119	Intermediate Similarity	NPC476990
0.7119	Intermediate Similarity	NPC478015
0.7113	Intermediate Similarity	NPC121478
0.7113	Intermediate Similarity	NPC73637
0.7103	Intermediate Similarity	NPC214200
0.7103	Intermediate Similarity	NPC228400
0.71	Intermediate Similarity	NPC198747
0.7097	Intermediate Similarity	NPC255447
0.7094	Intermediate Similarity	NPC220698
0.7091	Intermediate Similarity	NPC274089
0.7091	Intermediate Similarity	NPC473498
0.7091	Intermediate Similarity	NPC191215
0.7083	Intermediate Similarity	NPC184030
0.7083	Intermediate Similarity	NPC164449
0.7059	Intermediate Similarity	NPC273830
0.7059	Intermediate Similarity	NPC202521
0.7048	Intermediate Similarity	NPC3371
0.7043	Intermediate Similarity	NPC205652
0.704	Intermediate Similarity	NPC325479
0.704	Intermediate Similarity	NPC246913
0.7034	Intermediate Similarity	NPC268572
0.7027	Intermediate Similarity	NPC142297
0.7019	Intermediate Similarity	NPC476483
0.7016	Intermediate Similarity	NPC325651
0.7	Intermediate Similarity	NPC252878
0.6984	Remote Similarity	NPC244866
0.6983	Remote Similarity	NPC188010
0.6981	Remote Similarity	NPC324569
0.6972	Remote Similarity	NPC178902
0.6942	Remote Similarity	NPC474082
0.6942	Remote Similarity	NPC46427
0.6942	Remote Similarity	NPC6975
0.6942	Remote Similarity	NPC175726
0.6939	Remote Similarity	NPC283012
0.6939	Remote Similarity	NPC475199
0.6937	Remote Similarity	NPC45033
0.6923	Remote Similarity	NPC147957
0.6923	Remote Similarity	NPC323164
0.6916	Remote Similarity	NPC226096
0.6916	Remote Similarity	NPC108606
0.6916	Remote Similarity	NPC290515
0.6916	Remote Similarity	NPC164514
0.6916	Remote Similarity	NPC322598
0.6916	Remote Similarity	NPC303611
0.6909	Remote Similarity	NPC275467
0.6905	Remote Similarity	NPC326966
0.69	Remote Similarity	NPC99482
0.6897	Remote Similarity	NPC471318
0.6891	Remote Similarity	NPC43275
0.6882	Remote Similarity	NPC244738
0.6881	Remote Similarity	NPC318154
0.687	Remote Similarity	NPC273814
0.6869	Remote Similarity	NPC119677
0.6864	Remote Similarity	NPC283468
0.686	Remote Similarity	NPC109151
0.6847	Remote Similarity	NPC67043
0.6833	Remote Similarity	NPC190663
0.6833	Remote Similarity	NPC200964
0.6833	Remote Similarity	NPC80150
0.6829	Remote Similarity	NPC101719
0.6822	Remote Similarity	NPC472258
0.6818	Remote Similarity	NPC178681
0.6807	Remote Similarity	NPC122009
0.6803	Remote Similarity	NPC471314
0.6803	Remote Similarity	NPC471315
0.6797	Remote Similarity	NPC267237
0.6792	Remote Similarity	NPC215351
0.6792	Remote Similarity	NPC20142
0.6792	Remote Similarity	NPC108339
0.6783	Remote Similarity	NPC275410
0.678	Remote Similarity	NPC239357
0.6774	Remote Similarity	NPC208302
0.6769	Remote Similarity	NPC77992
0.6757	Remote Similarity	NPC147000
0.6757	Remote Similarity	NPC150254
0.6757	Remote Similarity	NPC226778
0.6757	Remote Similarity	NPC304761
0.6748	Remote Similarity	NPC22746
0.6748	Remote Similarity	NPC222466
0.6746	Remote Similarity	NPC200589
0.6735	Remote Similarity	NPC309279
0.6721	Remote Similarity	NPC160493
0.6721	Remote Similarity	NPC474862
0.672	Remote Similarity	NPC319766
0.67	Remote Similarity	NPC477770
0.6696	Remote Similarity	NPC473418
0.6694	Remote Similarity	NPC474479
0.6694	Remote Similarity	NPC95733
0.6694	Remote Similarity	NPC62101
0.6693	Remote Similarity	NPC474091
0.6667	Remote Similarity	NPC470926
0.6667	Remote Similarity	NPC472415
0.6667	Remote Similarity	NPC477839
0.6641	Remote Similarity	NPC132636
0.664	Remote Similarity	NPC29477
0.6637	Remote Similarity	NPC474804
0.6637	Remote Similarity	NPC474973
0.6637	Remote Similarity	NPC130898
0.6632	Remote Similarity	NPC112609
0.6632	Remote Similarity	NPC108218
0.6632	Remote Similarity	NPC122327
0.6632	Remote Similarity	NPC113000
0.6614	Remote Similarity	NPC300315
0.6613	Remote Similarity	NPC211218
0.6613	Remote Similarity	NPC307020
0.6612	Remote Similarity	NPC319950

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 NPC311242 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	559
0.2-0.3	1028
0.3-0.4	2325
0.4-0.5	3136
0.5-0.6	1528
0.6-0.7	400
0.7-0.8	60
0.8-0.85	6
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8526	High Similarity	NPD1814	Approved
0.8526	High Similarity	NPD6690	Approved
0.8526	High Similarity	NPD1812	Approved
0.8485	Intermediate Similarity	NPD4760	Clinical (unspecified phase)
0.8173	Intermediate Similarity	NPD6038	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD2487	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD1875	Phase 1
0.7981	Intermediate Similarity	NPD999	Phase 2
0.7944	Intermediate Similarity	NPD3644	Approved
0.7944	Intermediate Similarity	NPD3642	Approved
0.7944	Intermediate Similarity	NPD3643	Approved
0.79	Intermediate Similarity	NPD2895	Discontinued
0.79	Intermediate Similarity	NPD2507	Clinical (unspecified phase)
0.7879	Intermediate Similarity	NPD1080	Approved
0.781	Intermediate Similarity	NPD5717	Approved
0.78	Intermediate Similarity	NPD4814	Discontinued
0.7788	Intermediate Similarity	NPD1542	Approved
0.7778	Intermediate Similarity	NPD752	Approved
0.7768	Intermediate Similarity	NPD6360	Discontinued
0.7692	Intermediate Similarity	NPD4119	Approved
0.7692	Intermediate Similarity	NPD1540	Approved
0.7632	Intermediate Similarity	NPD4504	Clinical (unspecified phase)
0.7629	Intermediate Similarity	NPD9538	Approved
0.7611	Intermediate Similarity	NPD7522	Discontinued
0.7525	Intermediate Similarity	NPD719	Approved
0.7525	Intermediate Similarity	NPD720	Approved
0.7524	Intermediate Similarity	NPD5716	Approved
0.75	Intermediate Similarity	NPD2956	Clinical (unspecified phase)
0.7477	Intermediate Similarity	NPD1040	Phase 2
0.7451	Intermediate Similarity	NPD1081	Clinical (unspecified phase)
0.7434	Intermediate Similarity	NPD7508	Discontinued
0.7404	Intermediate Similarity	NPD4117	Approved
0.7383	Intermediate Similarity	NPD179	Clinical (unspecified phase)
0.7373	Intermediate Similarity	NPD5108	Clinical (unspecified phase)
0.7358	Intermediate Similarity	NPD4719	Phase 2
0.7328	Intermediate Similarity	NPD5981	Approved
0.7327	Intermediate Similarity	NPD530	Approved
0.7315	Intermediate Similarity	NPD1018	Approved
0.729	Intermediate Similarity	NPD5103	Approved
0.7281	Intermediate Similarity	NPD1348	Approved
0.7273	Intermediate Similarity	NPD187	Approved
0.7273	Intermediate Similarity	NPD7451	Discontinued
0.7257	Intermediate Similarity	NPD2658	Approved
0.7257	Intermediate Similarity	NPD3148	Approved
0.7257	Intermediate Similarity	NPD3149	Approved
0.7257	Intermediate Similarity	NPD3150	Approved
0.7257	Intermediate Similarity	NPD3147	Approved
0.7257	Intermediate Similarity	NPD2659	Approved
0.725	Intermediate Similarity	NPD5578	Approved
0.725	Intermediate Similarity	NPD5577	Clinical (unspecified phase)
0.7241	Intermediate Similarity	NPD2218	Phase 2
0.7241	Intermediate Similarity	NPD2217	Approved
0.7232	Intermediate Similarity	NPD3651	Discontinued
0.72	Intermediate Similarity	NPD1101	Approved
0.719	Intermediate Similarity	NPD6302	Clinical (unspecified phase)
0.7179	Intermediate Similarity	NPD1922	Discontinued
0.7172	Intermediate Similarity	NPD5252	Clinical (unspecified phase)
0.717	Intermediate Similarity	NPD1067	Discontinued
0.7168	Intermediate Similarity	NPD1762	Approved
0.7168	Intermediate Similarity	NPD1764	Approved
0.7143	Intermediate Similarity	NPD9566	Approved
0.7143	Intermediate Similarity	NPD2583	Phase 2
0.713	Intermediate Similarity	NPD4031	Approved
0.713	Intermediate Similarity	NPD4656	Approved
0.713	Intermediate Similarity	NPD4658	Approved
0.713	Intermediate Similarity	NPD4032	Approved
0.7119	Intermediate Similarity	NPD7342	Discontinued
0.7117	Intermediate Similarity	NPD2679	Approved
0.7117	Intermediate Similarity	NPD2678	Approved
0.7115	Intermediate Similarity	NPD3772	Phase 3
0.7083	Intermediate Similarity	NPD5702	Clinical (unspecified phase)
0.7073	Intermediate Similarity	NPD7828	Discontinued
0.7073	Intermediate Similarity	NPD4895	Clinical (unspecified phase)
0.7064	Intermediate Similarity	NPD3407	Phase 3
0.704	Intermediate Similarity	NPD8011	Discontinued
0.7037	Intermediate Similarity	NPD855	Approved
0.7037	Intermediate Similarity	NPD854	Approved
0.7027	Intermediate Similarity	NPD4095	Clinical (unspecified phase)
0.7019	Intermediate Similarity	NPD1394	Approved
0.7019	Intermediate Similarity	NPD1066	Discontinued
0.7019	Intermediate Similarity	NPD3718	Approved
0.7019	Intermediate Similarity	NPD3719	Approved
0.7018	Intermediate Similarity	NPD3066	Phase 2
0.7018	Intermediate Similarity	NPD4165	Phase 2
0.7016	Intermediate Similarity	NPD6359	Clinical (unspecified phase)
0.701	Intermediate Similarity	NPD3035	Approved
0.7	Intermediate Similarity	NPD564	Approved
0.7	Intermediate Similarity	NPD563	Approved
0.6991	Remote Similarity	NPD4253	Approved
0.6991	Remote Similarity	NPD4254	Approved
0.6984	Remote Similarity	NPD8118	Discontinued
0.6981	Remote Similarity	NPD528	Clinical (unspecified phase)
0.6972	Remote Similarity	NPD4229	Approved
0.6972	Remote Similarity	NPD4231	Approved
0.697	Remote Similarity	NPD2538	Approved
0.697	Remote Similarity	NPD2539	Approved
0.6957	Remote Similarity	NPD6854	Phase 3
0.6947	Remote Similarity	NPD4144	Approved
0.6947	Remote Similarity	NPD4147	Approved
0.6939	Remote Similarity	NPD4169	Approved
0.6939	Remote Similarity	NPD4170	Approved
0.6939	Remote Similarity	NPD4701	Clinical (unspecified phase)
0.6929	Remote Similarity	NPD8265	Approved
0.6923	Remote Similarity	NPD3123	Discovery
0.6923	Remote Similarity	NPD6775	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD1841	Clinical (unspecified phase)
0.6916	Remote Similarity	NPD1724	Approved
0.6916	Remote Similarity	NPD9612	Approved
0.6916	Remote Similarity	NPD9611	Approved
0.6916	Remote Similarity	NPD9609	Approved
0.69	Remote Similarity	NPD5916	Discontinued
0.6897	Remote Similarity	NPD5631	Phase 3
0.6885	Remote Similarity	NPD3676	Clinical (unspecified phase)
0.6882	Remote Similarity	NPD9728	Phase 1
0.6881	Remote Similarity	NPD4817	Approved
0.6881	Remote Similarity	NPD4818	Approved
0.6875	Remote Similarity	NPD6406	Approved
0.6864	Remote Similarity	NPD1837	Clinical (unspecified phase)
0.6863	Remote Similarity	NPD3345	Approved
0.686	Remote Similarity	NPD7462	Clinical (unspecified phase)
0.6857	Remote Similarity	NPD1409	Phase 3
0.6852	Remote Similarity	NPD9712	Approved
0.6842	Remote Similarity	NPD4025	Clinical (unspecified phase)
0.6837	Remote Similarity	NPD472	Approved
0.6837	Remote Similarity	NPD4026	Approved
0.6837	Remote Similarity	NPD4027	Approved
0.6829	Remote Similarity	NPD5367	Discontinued
0.6827	Remote Similarity	NPD3000	Approved
0.6827	Remote Similarity	NPD2998	Approved
0.6827	Remote Similarity	NPD2997	Approved
0.6827	Remote Similarity	NPD517	Discontinued
0.6818	Remote Similarity	NPD3680	Approved
0.6818	Remote Similarity	NPD3682	Approved
0.6818	Remote Similarity	NPD2244	Clinical (unspecified phase)
0.6807	Remote Similarity	NPD6093	Discontinued
0.6807	Remote Similarity	NPD4479	Discontinued
0.6803	Remote Similarity	NPD6624	Discontinued
0.68	Remote Similarity	NPD5178	Approved
0.6789	Remote Similarity	NPD1275	Phase 2
0.6786	Remote Similarity	NPD5706	Approved
0.6786	Remote Similarity	NPD7130	Phase 3
0.6786	Remote Similarity	NPD5704	Approved
0.6786	Remote Similarity	NPD5705	Approved
0.6783	Remote Similarity	NPD4991	Discontinued
0.678	Remote Similarity	NPD4431	Clinical (unspecified phase)
0.678	Remote Similarity	NPD5162	Approved
0.6777	Remote Similarity	NPD4651	Clinical (unspecified phase)
0.6772	Remote Similarity	NPD7908	Discontinued
0.6769	Remote Similarity	NPD8154	Clinical (unspecified phase)
0.6762	Remote Similarity	NPD159	Clinical (unspecified phase)
0.6759	Remote Similarity	NPD9711	Approved
0.6759	Remote Similarity	NPD9710	Approved
0.6757	Remote Similarity	NPD10	Approved
0.6757	Remote Similarity	NPD311	Approved
0.6757	Remote Similarity	NPD314	Approved
0.6757	Remote Similarity	NPD315	Approved
0.6757	Remote Similarity	NPD309	Approved
0.6757	Remote Similarity	NPD310	Approved
0.6754	Remote Similarity	NPD1107	Approved
0.6754	Remote Similarity	NPD1108	Approved
0.675	Remote Similarity	NPD2212	Approved
0.675	Remote Similarity	NPD2210	Approved
0.6731	Remote Similarity	NPD5915	Approved
0.6727	Remote Similarity	NPD1737	Approved
0.6727	Remote Similarity	NPD1736	Approved
0.6727	Remote Similarity	NPD1419	Approved
0.6727	Remote Similarity	NPD1417	Approved
0.6727	Remote Similarity	NPD1735	Approved
0.6726	Remote Similarity	NPD2243	Clinical (unspecified phase)
0.6721	Remote Similarity	NPD2173	Clinical (unspecified phase)
0.672	Remote Similarity	NPD5339	Clinical (unspecified phase)
0.6719	Remote Similarity	NPD7477	Discontinued
0.6698	Remote Similarity	NPD6549	Approved
0.6698	Remote Similarity	NPD6548	Approved
0.6695	Remote Similarity	NPD2622	Approved
0.6694	Remote Similarity	NPD6325	Discontinued
0.6694	Remote Similarity	NPD5723	Approved
0.6667	Remote Similarity	NPD5655	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD9701	Discontinued
0.6667	Remote Similarity	NPD998	Approved
0.6667	Remote Similarity	NPD7450	Phase 2
0.6667	Remote Similarity	NPD3683	Approved
0.6667	Remote Similarity	NPD4636	Approved
0.6667	Remote Similarity	NPD2584	Suspended
0.6667	Remote Similarity	NPD3681	Approved
0.6641	Remote Similarity	NPD6852	Discontinued
0.664	Remote Similarity	NPD2585	Clinical (unspecified phase)
0.6639	Remote Similarity	NPD3881	Discontinued
0.6639	Remote Similarity	NPD3421	Phase 3
0.6633	Remote Similarity	NPD1051	Approved
0.6633	Remote Similarity	NPD1052	Approved
0.6633	Remote Similarity	NPD1053	Approved
0.6632	Remote Similarity	NPD9591	Approved
0.6632	Remote Similarity	NPD9588	Approved
0.6632	Remote Similarity	NPD9593	Approved
0.6632	Remote Similarity	NPD9589	Approved
0.6632	Remote Similarity	NPD9590	Approved
0.6632	Remote Similarity	NPD9592	Approved
0.6632	Remote Similarity	NPD9594	Approved
0.6632	Remote Similarity	NPD80	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