NPASS Compound

Structure

CID9373 OpenBabel06191715332D 25 27 0 0 1 0 0 0 0 0999 V2000 -0.0000 1.0000 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 -0.5000 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 4.3301 -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 3.4641 -2.0000 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 -0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 2.5000 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 1.7321 -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 2.5981 -1.5000 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 -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 1 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 -0.8660 -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 -2.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -2.0000 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 -1.7321 4.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 22 1 0 0 0 0 2 25 1 0 0 0 0 3 4 2 0 0 0 0 3 5 1 0 0 0 0 4 6 1 0 0 0 0 5 7 2 0 0 0 0 6 14 2 0 0 0 0 7 14 1 0 0 0 0 8 10 1 0 0 0 0 8 15 2 0 0 0 0 9 11 2 0 0 0 0 9 15 1 0 0 0 0 10 16 2 0 0 0 0 11 16 1 0 0 0 0 12 14 1 0 0 0 0 13 15 1 0 0 0 0 13 18 2 0 0 0 0 16 25 1 0 0 0 0 17 12 1 6 0 0 0 17 20 1 0 0 0 0 17 21 1 0 0 0 0 18 19 1 0 0 0 0 18 22 1 0 0 0 0 19 21 2 0 0 0 0 19 23 1 0 0 0 0 20 22 1 0 0 0 0 20 24 2 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	336.15
Volume:	353.443
LogP:	2.75
LogD:	2.53
LogS:	-3.412
# Rotatable Bonds:	5
TPSA:	64.35
# H-Bond Aceptor:	5
# H-Bond Donor:	1
# Rings:	3
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.778
Synthetic Accessibility Score:	2.276
Fsp3:	0.2
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:	-4.681
MDCK Permeability:	3.401467256480828e-05
Pgp-inhibitor:	0.195
Pgp-substrate:	0.003
Human Intestinal Absorption (HIA):	0.005
20% Bioavailability (F20%):	0.001
30% Bioavailability (F30%):	0.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.038
Plasma Protein Binding (PPB):	97.30103302001953%
Volume Distribution (VD):	0.451
Pgp-substrate:	1.3107686042785645%

ADMET: Metabolism

CYP1A2-inhibitor:	0.167
CYP1A2-substrate:	0.83
CYP2C19-inhibitor:	0.749
CYP2C19-substrate:	0.781
CYP2C9-inhibitor:	0.768
CYP2C9-substrate:	0.908
CYP2D6-inhibitor:	0.068
CYP2D6-substrate:	0.491
CYP3A4-inhibitor:	0.478
CYP3A4-substrate:	0.876

ADMET: Excretion

Clearance (CL):	8.49
Half-life (T1/2):	0.811

ADMET: Toxicity

hERG Blockers:	0.024
Human Hepatotoxicity (H-HT):	0.517
Drug-inuced Liver Injury (DILI):	0.958
AMES Toxicity:	0.078
Rat Oral Acute Toxicity:	0.12
Maximum Recommended Daily Dose:	0.02
Skin Sensitization:	0.048
Carcinogencity:	0.428
Eye Corrosion:	0.003
Eye Irritation:	0.046
Respiratory Toxicity:	0.105

Download Data

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

Natural Product: NPC9373

Natural Product ID:	NPC9373
*Common Name:**	Nocazine C
IUPAC Name:	(3S,6Z)-3-benzyl-6-[(4-methoxyphenyl)methylidene]-1-methylpiperazine-2,5-dione
Synonyms:	nocazine C
Standard InCHIKey:	LNJXHMVOPQVJDF-XIDKLXSXSA-N
Standard InCHI:	InChI=1S/C20H20N2O3/c1-22-18(13-15-8-10-16(25-2)11-9-15)19(23)21-17(20(22)24)12-14-6-4-3-5-7-14/h3-11,13,17H,12H2,1-2H3,(H,21,23)/b18-13-/t17-/m0/s1
SMILES:	CN1/C(=Cc2ccc(cc2)OC)/C(=N[C@@H](Cc2ccccc2)C1=O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1835447
PubChem CID:	56600878
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
NPO14429	0cardiopsis dassonvillei	Species	0cardiopsaceae	Bacteria	isolated from marine sediments	The estuary of Yellow River, Dongying, Shandong Province, China	n.a.	PMID[21958359]
NPO14429	0cardiopsis dassonvillei	Species	0cardiopsaceae	Bacteria	n.a.	spore	n.a.	PMID[21958359]
NPO14429	0cardiopsis dassonvillei	Species	0cardiopsaceae	Bacteria	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
Others	1

Activity Type	# Activity
Cell Line	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT116	Cell Line	HL-60	Homo sapiens	IC50	>=	100000.0	nM	PMID[465103]
NPT81	Cell Line	A549	Homo sapiens	IC5	>=	100.0	uM	PMID[465103]

☑ 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 NPC9373 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	197
0.1-0.2	1767
0.2-0.3	8842
0.3-0.4	7995
0.4-0.5	8162
0.5-0.6	13777
0.6-0.7	1715
0.7-0.8	235
0.8-0.85	6
0.85-0.9	0
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.8582	High Similarity	NPC29650
0.8521	High Similarity	NPC138365
0.8366	Intermediate Similarity	NPC319320
0.8366	Intermediate Similarity	NPC287757
0.8267	Intermediate Similarity	NPC324081
0.8112	Intermediate Similarity	NPC257390
0.8088	Intermediate Similarity	NPC220698
0.8082	Intermediate Similarity	NPC313694
0.8082	Intermediate Similarity	NPC242159
0.7987	Intermediate Similarity	NPC254700
0.7958	Intermediate Similarity	NPC218323
0.7947	Intermediate Similarity	NPC16188
0.7914	Intermediate Similarity	NPC164608
0.7877	Intermediate Similarity	NPC266425
0.7857	Intermediate Similarity	NPC233702
0.7831	Intermediate Similarity	NPC32064
0.781	Intermediate Similarity	NPC258992
0.7716	Intermediate Similarity	NPC473502
0.7697	Intermediate Similarity	NPC279871
0.7692	Intermediate Similarity	NPC202198
0.7687	Intermediate Similarity	NPC470392
0.7662	Intermediate Similarity	NPC189908
0.7647	Intermediate Similarity	NPC138083
0.7647	Intermediate Similarity	NPC315542
0.7643	Intermediate Similarity	NPC43275
0.764	Intermediate Similarity	NPC191863
0.764	Intermediate Similarity	NPC133470
0.764	Intermediate Similarity	NPC289776
0.7622	Intermediate Similarity	NPC196091
0.7619	Intermediate Similarity	NPC45191
0.7616	Intermediate Similarity	NPC476989
0.7609	Intermediate Similarity	NPC303370
0.7602	Intermediate Similarity	NPC276120
0.7593	Intermediate Similarity	NPC472923
0.7589	Intermediate Similarity	NPC263835
0.7566	Intermediate Similarity	NPC212850
0.7566	Intermediate Similarity	NPC83289
0.7566	Intermediate Similarity	NPC189724
0.756	Intermediate Similarity	NPC269750
0.756	Intermediate Similarity	NPC194671
0.7532	Intermediate Similarity	NPC81026
0.753	Intermediate Similarity	NPC248670
0.7517	Intermediate Similarity	NPC124776
0.75	Intermediate Similarity	NPC211218
0.75	Intermediate Similarity	NPC245974
0.75	Intermediate Similarity	NPC323948
0.7484	Intermediate Similarity	NPC247298
0.7483	Intermediate Similarity	NPC283079
0.7471	Intermediate Similarity	NPC29531
0.7471	Intermediate Similarity	NPC174122
0.7471	Intermediate Similarity	NPC64140
0.7468	Intermediate Similarity	NPC266741
0.7465	Intermediate Similarity	NPC41801
0.7455	Intermediate Similarity	NPC186617
0.7452	Intermediate Similarity	NPC473491
0.7448	Intermediate Similarity	NPC62101
0.7448	Intermediate Similarity	NPC95733
0.7419	Intermediate Similarity	NPC473804
0.7414	Intermediate Similarity	NPC234069
0.741	Intermediate Similarity	NPC471568
0.741	Intermediate Similarity	NPC473693
0.7407	Intermediate Similarity	NPC469243
0.74	Intermediate Similarity	NPC169766
0.7397	Intermediate Similarity	NPC29477
0.7394	Intermediate Similarity	NPC256369
0.7391	Intermediate Similarity	NPC56635
0.7389	Intermediate Similarity	NPC132771
0.7384	Intermediate Similarity	NPC471049
0.7384	Intermediate Similarity	NPC294951
0.7384	Intermediate Similarity	NPC471050
0.7384	Intermediate Similarity	NPC471048
0.7381	Intermediate Similarity	NPC158277
0.7378	Intermediate Similarity	NPC223207
0.7372	Intermediate Similarity	NPC119569
0.7365	Intermediate Similarity	NPC89831
0.7362	Intermediate Similarity	NPC241794
0.7353	Intermediate Similarity	NPC475421
0.7333	Intermediate Similarity	NPC290755
0.7333	Intermediate Similarity	NPC304074
0.7333	Intermediate Similarity	NPC471771
0.7333	Intermediate Similarity	NPC244866
0.7333	Intermediate Similarity	NPC471953
0.7321	Intermediate Similarity	NPC137627
0.7321	Intermediate Similarity	NPC306804
0.732	Intermediate Similarity	NPC193528
0.7319	Intermediate Similarity	NPC166837
0.7315	Intermediate Similarity	NPC120251
0.7312	Intermediate Similarity	NPC39431
0.7305	Intermediate Similarity	NPC82963
0.7303	Intermediate Similarity	NPC471563
0.7301	Intermediate Similarity	NPC475544
0.7297	Intermediate Similarity	NPC296712
0.7292	Intermediate Similarity	NPC83279
0.7289	Intermediate Similarity	NPC294516
0.7289	Intermediate Similarity	NPC141957
0.7289	Intermediate Similarity	NPC328649
0.7289	Intermediate Similarity	NPC107938
0.7278	Intermediate Similarity	NPC159767
0.7278	Intermediate Similarity	NPC155506
0.7273	Intermediate Similarity	NPC63931
0.7273	Intermediate Similarity	NPC150712
0.7267	Intermediate Similarity	NPC476268
0.7257	Intermediate Similarity	NPC329731
0.7254	Intermediate Similarity	NPC38458
0.7254	Intermediate Similarity	NPC311737
0.725	Intermediate Similarity	NPC262166
0.7248	Intermediate Similarity	NPC325651
0.7237	Intermediate Similarity	NPC473360
0.7232	Intermediate Similarity	NPC473407
0.7232	Intermediate Similarity	NPC477526
0.7232	Intermediate Similarity	NPC473378
0.723	Intermediate Similarity	NPC301713
0.7225	Intermediate Similarity	NPC470903
0.7225	Intermediate Similarity	NPC470112
0.7225	Intermediate Similarity	NPC167763
0.7222	Intermediate Similarity	NPC321133
0.7222	Intermediate Similarity	NPC144314
0.7219	Intermediate Similarity	NPC118419
0.7219	Intermediate Similarity	NPC274732
0.7213	Intermediate Similarity	NPC311357
0.7208	Intermediate Similarity	NPC225745
0.7202	Intermediate Similarity	NPC40234
0.719	Intermediate Similarity	NPC237227
0.7188	Intermediate Similarity	NPC153644
0.7182	Intermediate Similarity	NPC50548
0.7181	Intermediate Similarity	NPC469666
0.7181	Intermediate Similarity	NPC251571
0.7176	Intermediate Similarity	NPC136797
0.7176	Intermediate Similarity	NPC476227
0.7176	Intermediate Similarity	NPC26108
0.7175	Intermediate Similarity	NPC163961
0.7175	Intermediate Similarity	NPC473305
0.7174	Intermediate Similarity	NPC473460
0.7167	Intermediate Similarity	NPC149962
0.716	Intermediate Similarity	NPC473580
0.716	Intermediate Similarity	NPC230611
0.7159	Intermediate Similarity	NPC4910
0.7153	Intermediate Similarity	NPC319950
0.7143	Intermediate Similarity	NPC299806
0.7143	Intermediate Similarity	NPC5194
0.7143	Intermediate Similarity	NPC280022
0.7143	Intermediate Similarity	NPC77992
0.7143	Intermediate Similarity	NPC261934
0.7143	Intermediate Similarity	NPC56685
0.7135	Intermediate Similarity	NPC473422
0.7134	Intermediate Similarity	NPC244336
0.7133	Intermediate Similarity	NPC155838
0.7123	Intermediate Similarity	NPC142577
0.7118	Intermediate Similarity	NPC273755
0.7114	Intermediate Similarity	NPC476353
0.711	Intermediate Similarity	NPC39822
0.7101	Intermediate Similarity	NPC198254
0.7101	Intermediate Similarity	NPC274198
0.7099	Intermediate Similarity	NPC478189
0.7097	Intermediate Similarity	NPC28641
0.7097	Intermediate Similarity	NPC194359
0.7097	Intermediate Similarity	NPC471316
0.7095	Intermediate Similarity	NPC204970
0.7086	Intermediate Similarity	NPC35961
0.7086	Intermediate Similarity	NPC52029
0.7086	Intermediate Similarity	NPC195749
0.7083	Intermediate Similarity	NPC302597
0.7081	Intermediate Similarity	NPC470019
0.7078	Intermediate Similarity	NPC11147
0.7078	Intermediate Similarity	NPC109580
0.7078	Intermediate Similarity	NPC180647
0.7076	Intermediate Similarity	NPC473402
0.7076	Intermediate Similarity	NPC473354
0.7073	Intermediate Similarity	NPC212699
0.7073	Intermediate Similarity	NPC207675
0.7063	Intermediate Similarity	NPC19290
0.7063	Intermediate Similarity	NPC254798
0.7059	Intermediate Similarity	NPC132308
0.7056	Intermediate Similarity	NPC328763
0.7051	Intermediate Similarity	NPC231572
0.7049	Intermediate Similarity	NPC123859
0.7042	Intermediate Similarity	NPC33742
0.7042	Intermediate Similarity	NPC118202
0.7041	Intermediate Similarity	NPC469505
0.7039	Intermediate Similarity	NPC326966
0.7035	Intermediate Similarity	NPC196243
0.7035	Intermediate Similarity	NPC50016
0.7032	Intermediate Similarity	NPC307682
0.7027	Intermediate Similarity	NPC307020
0.7024	Intermediate Similarity	NPC61004
0.7024	Intermediate Similarity	NPC469479
0.7018	Intermediate Similarity	NPC475532
0.7017	Intermediate Similarity	NPC59827
0.7017	Intermediate Similarity	NPC184933
0.7014	Intermediate Similarity	NPC470545
0.7012	Intermediate Similarity	NPC58661
0.7011	Intermediate Similarity	NPC242728
0.7007	Intermediate Similarity	NPC474862
0.7007	Intermediate Similarity	NPC27581
0.7006	Intermediate Similarity	NPC251439
0.7006	Intermediate Similarity	NPC470709
0.7	Intermediate Similarity	NPC276506
0.6993	Remote Similarity	NPC214869
0.6984	Remote Similarity	NPC471561
0.6983	Remote Similarity	NPC174629

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 NPC9373 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	141
0.1-0.2	499
0.2-0.3	990
0.3-0.4	1201
0.4-0.5	2655
0.5-0.6	2694
0.6-0.7	910
0.7-0.8	59
0.8-0.85	0
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8904	High Similarity	NPD7131	Phase 3
0.8881	High Similarity	NPD5481	Discontinued
0.8156	Intermediate Similarity	NPD4993	Discontinued
0.7911	Intermediate Similarity	NPD5967	Approved
0.7738	Intermediate Similarity	NPD7132	Clinical (unspecified phase)
0.7687	Intermediate Similarity	NPD5745	Approved
0.7632	Intermediate Similarity	NPD3655	Clinical (unspecified phase)
0.7622	Intermediate Similarity	NPD7608	Discontinued
0.7561	Intermediate Similarity	NPD7484	Phase 3
0.7561	Intermediate Similarity	NPD7485	Phase 3
0.7551	Intermediate Similarity	NPD5746	Approved
0.75	Intermediate Similarity	NPD1725	Approved
0.7412	Intermediate Similarity	NPD6297	Approved
0.7403	Intermediate Similarity	NPD7596	Clinical (unspecified phase)
0.7386	Intermediate Similarity	NPD7450	Phase 2
0.7378	Intermediate Similarity	NPD6533	Clinical (unspecified phase)
0.7356	Intermediate Similarity	NPD4515	Suspended
0.7355	Intermediate Similarity	NPD6860	Clinical (unspecified phase)
0.7355	Intermediate Similarity	NPD2976	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD7810	Phase 3
0.7333	Intermediate Similarity	NPD7811	Phase 3
0.7303	Intermediate Similarity	NPD4579	Clinical (unspecified phase)
0.7284	Intermediate Similarity	NPD7118	Clinical (unspecified phase)
0.7278	Intermediate Similarity	NPD6720	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD8031	Discontinued
0.726	Intermediate Similarity	NPD3676	Clinical (unspecified phase)
0.725	Intermediate Similarity	NPD6662	Clinical (unspecified phase)
0.7241	Intermediate Similarity	NPD6853	Approved
0.7241	Intermediate Similarity	NPD6851	Approved
0.7235	Intermediate Similarity	NPD5603	Clinical (unspecified phase)
0.7229	Intermediate Similarity	NPD6862	Phase 2
0.7222	Intermediate Similarity	NPD2668	Approved
0.7222	Intermediate Similarity	NPD2667	Approved
0.7216	Intermediate Similarity	NPD6608	Clinical (unspecified phase)
0.7215	Intermediate Similarity	NPD3281	Clinical (unspecified phase)
0.7211	Intermediate Similarity	NPD196	Phase 1
0.7202	Intermediate Similarity	NPD5183	Approved
0.7202	Intermediate Similarity	NPD5186	Approved
0.7195	Intermediate Similarity	NPD5294	Clinical (unspecified phase)
0.719	Intermediate Similarity	NPD3054	Approved
0.719	Intermediate Similarity	NPD3052	Approved
0.7188	Intermediate Similarity	NPD7303	Discontinued
0.7188	Intermediate Similarity	NPD1975	Clinical (unspecified phase)
0.7178	Intermediate Similarity	NPD2541	Clinical (unspecified phase)
0.7178	Intermediate Similarity	NPD7109	Clinical (unspecified phase)
0.7178	Intermediate Similarity	NPD7110	Phase 1
0.7152	Intermediate Similarity	NPD3056	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD3374	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD7318	Phase 3
0.7152	Intermediate Similarity	NPD5718	Phase 2
0.7143	Intermediate Similarity	NPD6583	Phase 3
0.7143	Intermediate Similarity	NPD5688	Approved
0.7143	Intermediate Similarity	NPD6582	Phase 2
0.7143	Intermediate Similarity	NPD5689	Approved
0.7118	Intermediate Similarity	NPD6894	Phase 1
0.7115	Intermediate Similarity	NPD5865	Clinical (unspecified phase)
0.7107	Intermediate Similarity	NPD6884	Clinical (unspecified phase)
0.7105	Intermediate Similarity	NPD2245	Discovery
0.7091	Intermediate Similarity	NPD6668	Clinical (unspecified phase)
0.7091	Intermediate Similarity	NPD6060	Clinical (unspecified phase)
0.7081	Intermediate Similarity	NPD6390	Discontinued
0.7063	Intermediate Similarity	NPD3596	Phase 2
0.7059	Intermediate Similarity	NPD2388	Discontinued
0.7059	Intermediate Similarity	NPD3140	Approved
0.7059	Intermediate Similarity	NPD3142	Approved
0.7052	Intermediate Similarity	NPD5484	Approved
0.7052	Intermediate Similarity	NPD5485	Approved
0.7051	Intermediate Similarity	NPD2239	Approved
0.7051	Intermediate Similarity	NPD2240	Approved
0.7044	Intermediate Similarity	NPD3692	Discontinued
0.7044	Intermediate Similarity	NPD5241	Discontinued
0.7044	Intermediate Similarity	NPD2219	Phase 1
0.7037	Intermediate Similarity	NPD1670	Discontinued
0.7034	Intermediate Similarity	NPD2595	Approved
0.7034	Intermediate Similarity	NPD2594	Approved
0.7032	Intermediate Similarity	NPD743	Approved
0.7031	Intermediate Similarity	NPD8149	Discontinued
0.703	Intermediate Similarity	NPD7317	Phase 3
0.7027	Intermediate Similarity	NPD1669	Approved
0.7027	Intermediate Similarity	NPD4659	Approved
0.7025	Intermediate Similarity	NPD6364	Approved
0.7025	Intermediate Similarity	NPD2459	Approved
0.7025	Intermediate Similarity	NPD2458	Approved
0.7025	Intermediate Similarity	NPD44	Approved
0.7025	Intermediate Similarity	NPD2460	Phase 3
0.7022	Intermediate Similarity	NPD7291	Discontinued
0.7019	Intermediate Similarity	NPD2335	Discontinued
0.7018	Intermediate Similarity	NPD5078	Clinical (unspecified phase)
0.7013	Intermediate Similarity	NPD4618	Approved
0.7013	Intermediate Similarity	NPD4622	Approved
0.7012	Intermediate Similarity	NPD6875	Approved
0.7012	Intermediate Similarity	NPD6502	Phase 2
0.7012	Intermediate Similarity	NPD6876	Approved
0.7012	Intermediate Similarity	NPD2592	Discontinued
0.7011	Intermediate Similarity	NPD6654	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD6584	Phase 3
0.7	Intermediate Similarity	NPD3479	Discontinued
0.6989	Remote Similarity	NPD7280	Phase 3
0.6989	Remote Similarity	NPD7281	Phase 3
0.6986	Remote Similarity	NPD2423	Clinical (unspecified phase)
0.6982	Remote Similarity	NPD2904	Discontinued
0.6981	Remote Similarity	NPD1662	Clinical (unspecified phase)
0.698	Remote Similarity	NPD7258	Clinical (unspecified phase)
0.6971	Remote Similarity	NPD5192	Clinical (unspecified phase)
0.6966	Remote Similarity	NPD6581	Approved
0.6966	Remote Similarity	NPD6580	Approved
0.6959	Remote Similarity	NPD5108	Clinical (unspecified phase)
0.6946	Remote Similarity	NPD3560	Approved
0.6946	Remote Similarity	NPD3557	Approved
0.6946	Remote Similarity	NPD3558	Approved
0.6946	Remote Similarity	NPD3559	Clinical (unspecified phase)
0.6946	Remote Similarity	NPD3556	Approved
0.6944	Remote Similarity	NPD5994	Discontinued
0.6943	Remote Similarity	NPD3175	Clinical (unspecified phase)
0.6943	Remote Similarity	NPD1538	Phase 1
0.6943	Remote Similarity	NPD4477	Approved
0.6943	Remote Similarity	NPD4476	Approved
0.6943	Remote Similarity	NPD1519	Approved
0.6943	Remote Similarity	NPD1537	Approved
0.6941	Remote Similarity	NPD2889	Approved
0.6941	Remote Similarity	NPD2888	Approved
0.6941	Remote Similarity	NPD2890	Approved
0.6941	Remote Similarity	NPD2017	Approved
0.6936	Remote Similarity	NPD6645	Clinical (unspecified phase)
0.6933	Remote Similarity	NPD4104	Clinical (unspecified phase)
0.6933	Remote Similarity	NPD4103	Phase 2
0.6928	Remote Similarity	NPD5355	Approved
0.6928	Remote Similarity	NPD5356	Approved
0.6928	Remote Similarity	NPD7945	Clinical (unspecified phase)
0.6927	Remote Similarity	NPD4435	Approved
0.6923	Remote Similarity	NPD1536	Approved
0.6919	Remote Similarity	NPD3451	Clinical (unspecified phase)
0.6919	Remote Similarity	NPD6607	Clinical (unspecified phase)
0.6918	Remote Similarity	NPD6830	Clinical (unspecified phase)
0.6914	Remote Similarity	NPD5348	Clinical (unspecified phase)
0.6914	Remote Similarity	NPD3536	Discontinued
0.6914	Remote Similarity	NPD5556	Clinical (unspecified phase)
0.6913	Remote Similarity	NPD1421	Approved
0.6913	Remote Similarity	NPD1420	Approved
0.691	Remote Similarity	NPD6967	Phase 2
0.6901	Remote Similarity	NPD2517	Approved
0.6898	Remote Similarity	NPD3802	Phase 3
0.6897	Remote Similarity	NPD3965	Phase 1
0.6894	Remote Similarity	NPD6666	Approved
0.6894	Remote Similarity	NPD6667	Approved
0.689	Remote Similarity	NPD5267	Discontinued
0.6889	Remote Similarity	NPD5112	Approved
0.6889	Remote Similarity	NPD5113	Approved
0.6889	Remote Similarity	NPD5114	Approved
0.6887	Remote Similarity	NPD2990	Approved
0.6887	Remote Similarity	NPD7018	Phase 2
0.6887	Remote Similarity	NPD2987	Approved
0.6886	Remote Similarity	NPD6818	Clinical (unspecified phase)
0.6883	Remote Similarity	NPD7477	Discontinued
0.6882	Remote Similarity	NPD2042	Clinical (unspecified phase)
0.6882	Remote Similarity	NPD2041	Clinical (unspecified phase)
0.6882	Remote Similarity	NPD6746	Phase 2
0.6879	Remote Similarity	NPD5966	Clinical (unspecified phase)
0.6879	Remote Similarity	NPD5602	Clinical (unspecified phase)
0.6872	Remote Similarity	NPD4434	Approved
0.6871	Remote Similarity	NPD7613	Discontinued
0.6868	Remote Similarity	NPD4539	Phase 1
0.6863	Remote Similarity	NPD3136	Phase 2
0.6863	Remote Similarity	NPD5163	Phase 2
0.686	Remote Similarity	NPD8051	Clinical (unspecified phase)
0.6851	Remote Similarity	NPD6505	Approved
0.6851	Remote Similarity	NPD6504	Approved
0.6849	Remote Similarity	NPD2486	Discontinued
0.6848	Remote Similarity	NPD6523	Clinical (unspecified phase)
0.6848	Remote Similarity	NPD3769	Discontinued
0.6848	Remote Similarity	NPD824	Approved
0.6846	Remote Similarity	NPD2232	Approved
0.6846	Remote Similarity	NPD2230	Approved
0.6846	Remote Similarity	NPD2562	Approved
0.6846	Remote Similarity	NPD2561	Approved
0.6846	Remote Similarity	NPD2233	Approved
0.6845	Remote Similarity	NPD6063	Approved
0.6842	Remote Similarity	NPD2516	Approved
0.6835	Remote Similarity	NPD1523	Approved
0.6835	Remote Similarity	NPD1522	Approved
0.6833	Remote Similarity	NPD4157	Discontinued
0.6831	Remote Similarity	NPD6312	Discontinued
0.6831	Remote Similarity	NPD7669	Phase 3
0.6829	Remote Similarity	NPD7427	Discontinued
0.6829	Remote Similarity	NPD2122	Discontinued
0.6828	Remote Similarity	NPD3123	Discovery
0.6826	Remote Similarity	NPD8019	Approved
0.6826	Remote Similarity	NPD3812	Clinical (unspecified phase)
0.6826	Remote Similarity	NPD7248	Discontinued
0.6826	Remote Similarity	NPD7577	Discontinued
0.6824	Remote Similarity	NPD3421	Phase 3
0.6824	Remote Similarity	NPD8245	Clinical (unspecified phase)
0.6824	Remote Similarity	NPD3847	Discontinued
0.6818	Remote Similarity	NPD6211	Clinical (unspecified phase)
0.6815	Remote Similarity	NPD1520	Approved
0.6815	Remote Similarity	NPD1521	Approved
0.681	Remote Similarity	NPD4123	Phase 3
0.681	Remote Similarity	NPD2874	Phase 2
0.6803	Remote Similarity	NPD6382	Discontinued
0.6802	Remote Similarity	NPD6747	Phase 1

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