NPASS Compound

Structure

NPC470017 OpenBabel07101719522D 23 26 0 0 0 0 0 0 0 0999 V2000 3.4641 -4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8965 -1.6241 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8388 -2.3928 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2596 -1.1898 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1444 -2.7272 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 0.8660 0.5000 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 -0.5651 -1.5243 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5075 -2.2930 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 0.8660 -2.5000 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 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -1.0000 0.0000 C 0 0 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 0.1294 -2.7272 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 3.4641 -1.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -0.0196 -3.7160 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 3.4641 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 23 1 0 0 0 0 2 3 2 0 0 0 0 2 4 1 0 0 0 0 3 5 1 0 0 0 0 4 9 2 0 0 0 0 5 10 2 0 0 0 0 6 7 2 0 0 0 0 6 11 1 0 0 0 0 7 18 1 0 0 0 0 8 12 2 0 0 0 0 8 13 1 0 0 0 0 9 10 1 0 0 0 0 9 15 1 0 0 0 0 10 17 1 0 0 0 0 11 14 2 0 0 0 0 11 16 1 0 0 0 0 12 14 1 0 0 0 0 12 17 1 0 0 0 0 13 16 2 0 0 0 0 13 23 1 0 0 0 0 14 15 1 0 0 0 0 15 18 2 0 0 0 0 16 19 1 0 0 0 0 17 20 2 0 0 0 0 19 21 2 0 0 0 0 19 22 2 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	306.06
Volume:	299.152
LogP:	3.369
LogD:	2.863
LogS:	-6.244
# Rotatable Bonds:	2
TPSA:	82.33
# H-Bond Aceptor:	6
# H-Bond Donor:	0
# Rings:	4
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.419
Synthetic Accessibility Score:	2.481
Fsp3:	0.059
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:	-4.697
MDCK Permeability:	6.853624654468149e-05
Pgp-inhibitor:	0.307
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.001
30% Bioavailability (F30%):	0.036

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.179
Plasma Protein Binding (PPB):	97.3967514038086%
Volume Distribution (VD):	0.526
Pgp-substrate:	1.523471713066101%

ADMET: Metabolism

CYP1A2-inhibitor:	0.94
CYP1A2-substrate:	0.751
CYP2C19-inhibitor:	0.792
CYP2C19-substrate:	0.134
CYP2C9-inhibitor:	0.826
CYP2C9-substrate:	0.875
CYP2D6-inhibitor:	0.428
CYP2D6-substrate:	0.353
CYP3A4-inhibitor:	0.656
CYP3A4-substrate:	0.136

ADMET: Excretion

Clearance (CL):	1.644
Half-life (T1/2):	0.176

ADMET: Toxicity

hERG Blockers:	0.223
Human Hepatotoxicity (H-HT):	0.673
Drug-inuced Liver Injury (DILI):	0.949
AMES Toxicity:	0.959
Rat Oral Acute Toxicity:	0.047
Maximum Recommended Daily Dose:	0.761
Skin Sensitization:	0.608
Carcinogencity:	0.922
Eye Corrosion:	0.006
Eye Irritation:	0.922
Respiratory Toxicity:	0.936

Download Data

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

Natural Product: NPC470017

Natural Product ID:	NPC470017
*Common Name:**	DLZDROOSVPZQLL-UHFFFAOYSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	DLZDROOSVPZQLL-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C17H10N2O4/c1-23-13-8-12-14-11(16(13)19(21)22)6-7-18-15(14)9-4-2-3-5-10(9)17(12)20/h2-8H,1H3
SMILES:	COC1=C(C2=C3C(=C1)C(=O)C4=CC=CC=C4C3=NC=C2)[N+](=O)[O-]
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1651049
PubChem CID:	50908785
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000279] Alkaloids and derivatives [CHEMONTID:0003018] Isoaporphines [CHEMONTID:0004118] Oxoisoaporphines

*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
NPO21789	Sciadotenia toxifera	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20961068]
NPO21789	Sciadotenia toxifera	Species	Menispermaceae	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	8
Others	4

Activity Type	# Activity
Cell Line	6
NON-MOLECULAR	1
Organism	1
Others	4

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT196	Cell Line	AGS	Homo sapiens	IC50	=	4500.0	nM	PMID[545083]
NPT171	Cell Line	MRC5	Homo sapiens	IC50	=	10200.0	nM	PMID[545084]
NPT1505	Cell Line	J82	Homo sapiens	IC50	=	25400.0	nM	PMID[545085]
NPT1506	Cell Line	SK-MES-1	Homo sapiens	IC50	=	17100.0	nM	PMID[545085]
NPT171	Cell Line	MRC5	Homo sapiens	IC50	=	10200.0	nM	PMID[545085]
NPT196	Cell Line	AGS	Homo sapiens	IC50	=	4500.0	nM	PMID[545085]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	4500.0	nM	PMID[545083]
NPT2	Others	Unspecified		Ratio IC50	=	0.49	n.a.	PMID[545084]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	21000.0	nM	PMID[545084]
NPT27	Others	Unspecified		Ratio IC50	=	2.3	n.a.	PMID[545085]
NPT27	Others	Unspecified		Ratio IC50	=	0.6	n.a.	PMID[545085]
NPT27	Others	Unspecified		Ratio IC50	=	0.4	n.a.	PMID[545085]

☑ 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 NPC470017 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	683
0.1-0.2	3965
0.2-0.3	13076
0.3-0.4	5243
0.4-0.5	14698
0.5-0.6	3269
0.6-0.7	1508
0.7-0.8	236
0.8-0.85	11
0.85-0.9	4
0.9-0.95	2
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9763	High Similarity	NPC470022
0.9429	High Similarity	NPC470018
0.9202	High Similarity	NPC74575
0.9032	High Similarity	NPC49547
0.8942	High Similarity	NPC470020
0.8717	High Similarity	NPC208522
0.8603	High Similarity	NPC270515
0.8291	Intermediate Similarity	NPC137353
0.8288	Intermediate Similarity	NPC322482
0.8243	Intermediate Similarity	NPC210434
0.8225	Intermediate Similarity	NPC72905
0.819	Intermediate Similarity	NPC142385
0.8186	Intermediate Similarity	NPC24019
0.8174	Intermediate Similarity	NPC132385
0.8143	Intermediate Similarity	NPC470023
0.808	Intermediate Similarity	NPC216612
0.8079	Intermediate Similarity	NPC22481
0.8052	Intermediate Similarity	NPC472061
0.8009	Intermediate Similarity	NPC146976
0.7974	Intermediate Similarity	NPC189903
0.7974	Intermediate Similarity	NPC182907
0.7965	Intermediate Similarity	NPC90875
0.7964	Intermediate Similarity	NPC236668
0.7957	Intermediate Similarity	NPC233334
0.7948	Intermediate Similarity	NPC278525
0.7934	Intermediate Similarity	NPC470021
0.7931	Intermediate Similarity	NPC108342
0.792	Intermediate Similarity	NPC144452
0.7911	Intermediate Similarity	NPC225279
0.7835	Intermediate Similarity	NPC474688
0.7826	Intermediate Similarity	NPC274640
0.7811	Intermediate Similarity	NPC253675
0.7806	Intermediate Similarity	NPC15406
0.7787	Intermediate Similarity	NPC166722
0.7773	Intermediate Similarity	NPC124313
0.7764	Intermediate Similarity	NPC207283
0.7764	Intermediate Similarity	NPC84164
0.7735	Intermediate Similarity	NPC39370
0.7722	Intermediate Similarity	NPC210296
0.7692	Intermediate Similarity	NPC329631
0.765	Intermediate Similarity	NPC473186
0.7647	Intermediate Similarity	NPC475844
0.7644	Intermediate Similarity	NPC39500
0.7634	Intermediate Similarity	NPC187501
0.7632	Intermediate Similarity	NPC208084
0.7613	Intermediate Similarity	NPC183537
0.7589	Intermediate Similarity	NPC188420
0.7556	Intermediate Similarity	NPC208284
0.7555	Intermediate Similarity	NPC17565
0.7541	Intermediate Similarity	NPC77878
0.7534	Intermediate Similarity	NPC193238
0.7511	Intermediate Similarity	NPC184408
0.75	Intermediate Similarity	NPC51388
0.75	Intermediate Similarity	NPC133140
0.75	Intermediate Similarity	NPC195268
0.7489	Intermediate Similarity	NPC323345
0.7489	Intermediate Similarity	NPC149471
0.7489	Intermediate Similarity	NPC470164
0.7489	Intermediate Similarity	NPC271215
0.7458	Intermediate Similarity	NPC41501
0.7458	Intermediate Similarity	NPC474701
0.7456	Intermediate Similarity	NPC235076
0.7455	Intermediate Similarity	NPC476578
0.7455	Intermediate Similarity	NPC476582
0.7455	Intermediate Similarity	NPC4071
0.7445	Intermediate Similarity	NPC251160
0.7425	Intermediate Similarity	NPC65277
0.7424	Intermediate Similarity	NPC274982
0.7414	Intermediate Similarity	NPC280799
0.7412	Intermediate Similarity	NPC324361
0.7411	Intermediate Similarity	NPC300156
0.7411	Intermediate Similarity	NPC45190
0.7401	Intermediate Similarity	NPC220337
0.7393	Intermediate Similarity	NPC179287
0.7384	Intermediate Similarity	NPC477112
0.7378	Intermediate Similarity	NPC4687
0.7378	Intermediate Similarity	NPC249583
0.7375	Intermediate Similarity	NPC235685
0.7368	Intermediate Similarity	NPC474428
0.7366	Intermediate Similarity	NPC36229
0.7366	Intermediate Similarity	NPC16452
0.7366	Intermediate Similarity	NPC476581
0.7359	Intermediate Similarity	NPC100079
0.7359	Intermediate Similarity	NPC23614
0.7359	Intermediate Similarity	NPC204446
0.735	Intermediate Similarity	NPC122436
0.7349	Intermediate Similarity	NPC53534
0.7344	Intermediate Similarity	NPC101350
0.7342	Intermediate Similarity	NPC234197
0.7336	Intermediate Similarity	NPC162530
0.7328	Intermediate Similarity	NPC46451
0.7316	Intermediate Similarity	NPC293151
0.7304	Intermediate Similarity	NPC237740
0.73	Intermediate Similarity	NPC246381
0.7289	Intermediate Similarity	NPC327592
0.7284	Intermediate Similarity	NPC119134
0.7281	Intermediate Similarity	NPC199667
0.7269	Intermediate Similarity	NPC82548
0.7257	Intermediate Similarity	NPC317373
0.7249	Intermediate Similarity	NPC87413
0.7244	Intermediate Similarity	NPC152620
0.7244	Intermediate Similarity	NPC475774
0.7241	Intermediate Similarity	NPC473513
0.7241	Intermediate Similarity	NPC169402
0.7238	Intermediate Similarity	NPC260434
0.7237	Intermediate Similarity	NPC174758
0.7237	Intermediate Similarity	NPC473181
0.7234	Intermediate Similarity	NPC118121
0.7234	Intermediate Similarity	NPC122463
0.7232	Intermediate Similarity	NPC31930
0.7229	Intermediate Similarity	NPC118228
0.7225	Intermediate Similarity	NPC313189
0.7225	Intermediate Similarity	NPC308943
0.722	Intermediate Similarity	NPC287437
0.7217	Intermediate Similarity	NPC310211
0.7217	Intermediate Similarity	NPC308137
0.7217	Intermediate Similarity	NPC264176
0.7213	Intermediate Similarity	NPC148889
0.721	Intermediate Similarity	NPC46561
0.7205	Intermediate Similarity	NPC290689
0.7195	Intermediate Similarity	NPC146724
0.7191	Intermediate Similarity	NPC60621
0.7188	Intermediate Similarity	NPC477019
0.7185	Intermediate Similarity	NPC257851
0.7185	Intermediate Similarity	NPC478078
0.7168	Intermediate Similarity	NPC245816
0.7168	Intermediate Similarity	NPC476138
0.716	Intermediate Similarity	NPC6786
0.7155	Intermediate Similarity	NPC116238
0.7149	Intermediate Similarity	NPC135549
0.7143	Intermediate Similarity	NPC478083
0.7143	Intermediate Similarity	NPC472098
0.7143	Intermediate Similarity	NPC112206
0.7143	Intermediate Similarity	NPC53069
0.7143	Intermediate Similarity	NPC473180
0.7143	Intermediate Similarity	NPC94157
0.7143	Intermediate Similarity	NPC202768
0.7143	Intermediate Similarity	NPC202605
0.7143	Intermediate Similarity	NPC296482
0.7143	Intermediate Similarity	NPC318299
0.7137	Intermediate Similarity	NPC173080
0.7137	Intermediate Similarity	NPC285558
0.713	Intermediate Similarity	NPC267928
0.713	Intermediate Similarity	NPC309845
0.713	Intermediate Similarity	NPC471304
0.7119	Intermediate Similarity	NPC198503
0.7112	Intermediate Similarity	NPC317752
0.7103	Intermediate Similarity	NPC478045
0.71	Intermediate Similarity	NPC146418
0.7076	Intermediate Similarity	NPC150239
0.7076	Intermediate Similarity	NPC472099
0.7076	Intermediate Similarity	NPC174760
0.7074	Intermediate Similarity	NPC222561
0.7069	Intermediate Similarity	NPC96405
0.7069	Intermediate Similarity	NPC171409
0.7069	Intermediate Similarity	NPC38237
0.7064	Intermediate Similarity	NPC247803
0.7059	Intermediate Similarity	NPC94842
0.7056	Intermediate Similarity	NPC84347
0.7054	Intermediate Similarity	NPC90229
0.7048	Intermediate Similarity	NPC328318
0.7048	Intermediate Similarity	NPC328596
0.7043	Intermediate Similarity	NPC39679
0.7043	Intermediate Similarity	NPC287208
0.7042	Intermediate Similarity	NPC157931
0.704	Intermediate Similarity	NPC63971
0.704	Intermediate Similarity	NPC91868
0.7039	Intermediate Similarity	NPC476287
0.7039	Intermediate Similarity	NPC232225
0.7034	Intermediate Similarity	NPC288987
0.7026	Intermediate Similarity	NPC9894
0.702	Intermediate Similarity	NPC15801
0.7013	Intermediate Similarity	NPC174672
0.7012	Intermediate Similarity	NPC471762
0.7012	Intermediate Similarity	NPC134637
0.7009	Intermediate Similarity	NPC55470
0.7004	Intermediate Similarity	NPC323969
0.7004	Intermediate Similarity	NPC174049
0.7004	Intermediate Similarity	NPC276657
0.7	Intermediate Similarity	NPC161801
0.7	Intermediate Similarity	NPC283117
0.6996	Remote Similarity	NPC230403
0.6992	Remote Similarity	NPC96321
0.6992	Remote Similarity	NPC131885
0.6992	Remote Similarity	NPC473041
0.6991	Remote Similarity	NPC280714
0.6986	Remote Similarity	NPC282103
0.6983	Remote Similarity	NPC167860
0.6983	Remote Similarity	NPC123976
0.6978	Remote Similarity	NPC224928
0.6968	Remote Similarity	NPC242928
0.6967	Remote Similarity	NPC141053
0.696	Remote Similarity	NPC176538
0.6958	Remote Similarity	NPC473449
0.6953	Remote Similarity	NPC294375
0.6951	Remote Similarity	NPC280964
0.6951	Remote Similarity	NPC114335
0.6951	Remote Similarity	NPC184225
0.6951	Remote Similarity	NPC141915
0.694	Remote Similarity	NPC185782

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 NPC470017 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	385
0.1-0.2	674
0.2-0.3	1056
0.3-0.4	1550
0.4-0.5	2660
0.5-0.6	2019
0.6-0.7	748
0.7-0.8	58
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
0.7982	Intermediate Similarity	NPD4429	Discontinued
0.7841	Intermediate Similarity	NPD2285	Clinical (unspecified phase)
0.7797	Intermediate Similarity	NPD6790	Phase 1
0.7792	Intermediate Similarity	NPD5801	Clinical (unspecified phase)
0.7743	Intermediate Similarity	NPD7395	Discontinued
0.7692	Intermediate Similarity	NPD6741	Clinical (unspecified phase)
0.7639	Intermediate Similarity	NPD5022	Discontinued
0.7598	Intermediate Similarity	NPD6242	Discontinued
0.7593	Intermediate Similarity	NPD5488	Discontinued
0.7542	Intermediate Similarity	NPD6716	Phase 1
0.7532	Intermediate Similarity	NPD6160	Clinical (unspecified phase)
0.7522	Intermediate Similarity	NPD7069	Discontinued
0.75	Intermediate Similarity	NPD3924	Approved
0.75	Intermediate Similarity	NPD7925	Phase 2
0.75	Intermediate Similarity	NPD7924	Phase 2
0.75	Intermediate Similarity	NPD3922	Approved
0.75	Intermediate Similarity	NPD3923	Approved
0.75	Intermediate Similarity	NPD3921	Approved
0.746	Intermediate Similarity	NPD8091	Phase 3
0.7455	Intermediate Similarity	NPD5429	Discontinued
0.7434	Intermediate Similarity	NPD1166	Clinical (unspecified phase)
0.7422	Intermediate Similarity	NPD7467	Discontinued
0.7414	Intermediate Similarity	NPD6298	Discontinued
0.7407	Intermediate Similarity	NPD5483	Clinical (unspecified phase)
0.7358	Intermediate Similarity	NPD6525	Clinical (unspecified phase)
0.7339	Intermediate Similarity	NPD4926	Clinical (unspecified phase)
0.7328	Intermediate Similarity	NPD3763	Approved
0.725	Intermediate Similarity	NPD5040	Clinical (unspecified phase)
0.7243	Intermediate Similarity	NPD7414	Clinical (unspecified phase)
0.7197	Intermediate Similarity	NPD8052	Clinical (unspecified phase)
0.719	Intermediate Similarity	NPD5891	Approved
0.7181	Intermediate Similarity	NPD7010	Phase 3
0.7178	Intermediate Similarity	NPD6494	Phase 2
0.7155	Intermediate Similarity	NPD7710	Clinical (unspecified phase)
0.7149	Intermediate Similarity	NPD5482	Discontinued
0.7143	Intermediate Similarity	NPD4889	Approved
0.7143	Intermediate Similarity	NPD3816	Phase 1
0.7143	Intermediate Similarity	NPD3815	Phase 1
0.7137	Intermediate Similarity	NPD6568	Discontinued
0.7119	Intermediate Similarity	NPD3006	Discontinued
0.7105	Intermediate Similarity	NPD5530	Phase 1
0.7104	Intermediate Similarity	NPD6569	Phase 2
0.7102	Intermediate Similarity	NPD2921	Clinical (unspecified phase)
0.71	Intermediate Similarity	NPD4502	Phase 2
0.7089	Intermediate Similarity	NPD1856	Discontinued
0.7085	Intermediate Similarity	NPD6550	Discontinued
0.7082	Intermediate Similarity	NPD7538	Clinical (unspecified phase)
0.7082	Intermediate Similarity	NPD3257	Approved
0.7074	Intermediate Similarity	NPD7222	Phase 2
0.7073	Intermediate Similarity	NPD7417	Discontinued
0.7071	Intermediate Similarity	NPD7426	Phase 1
0.7064	Intermediate Similarity	NPD3354	Phase 2
0.7059	Intermediate Similarity	NPD6531	Approved
0.7059	Intermediate Similarity	NPD6530	Approved
0.7059	Intermediate Similarity	NPD2334	Discontinued
0.7054	Intermediate Similarity	NPD5479	Discontinued
0.7048	Intermediate Similarity	NPD6477	Clinical (unspecified phase)
0.7042	Intermediate Similarity	NPD7268	Clinical (unspecified phase)
0.7042	Intermediate Similarity	NPD3259	Approved
0.7034	Intermediate Similarity	NPD6770	Approved
0.7033	Intermediate Similarity	NPD8016	Phase 3
0.7033	Intermediate Similarity	NPD8017	Clinical (unspecified phase)
0.7029	Intermediate Similarity	NPD6247	Clinical (unspecified phase)
0.7029	Intermediate Similarity	NPD7586	Clinical (unspecified phase)
0.7028	Intermediate Similarity	NPD8100	Phase 3
0.7026	Intermediate Similarity	NPD6567	Clinical (unspecified phase)
0.7017	Intermediate Similarity	NPD6824	Clinical (unspecified phase)
0.7012	Intermediate Similarity	NPD3809	Discontinued
0.7009	Intermediate Similarity	NPD5512	Phase 3
0.7009	Intermediate Similarity	NPD5417	Clinical (unspecified phase)
0.6991	Remote Similarity	NPD3920	Phase 2
0.6987	Remote Similarity	NPD4795	Phase 2
0.6987	Remote Similarity	NPD3946	Clinical (unspecified phase)
0.6972	Remote Similarity	NPD4369	Phase 2
0.6971	Remote Similarity	NPD7994	Phase 2
0.6964	Remote Similarity	NPD7885	Phase 2
0.6964	Remote Similarity	NPD7886	Phase 2
0.6964	Remote Similarity	NPD4418	Discontinued
0.6962	Remote Similarity	NPD3258	Approved
0.6955	Remote Similarity	NPD7688	Phase 1
0.6949	Remote Similarity	NPD3326	Clinical (unspecified phase)
0.6946	Remote Similarity	NPD6995	Phase 1
0.6944	Remote Similarity	NPD8101	Phase 3
0.6943	Remote Similarity	NPD5513	Phase 2
0.6936	Remote Similarity	NPD6140	Clinical (unspecified phase)
0.6933	Remote Similarity	NPD3478	Clinical (unspecified phase)
0.6933	Remote Similarity	NPD3477	Phase 2
0.6933	Remote Similarity	NPD7858	Clinical (unspecified phase)
0.6929	Remote Similarity	NPD8463	Approved
0.6926	Remote Similarity	NPD7708	Approved
0.692	Remote Similarity	NPD7206	Clinical (unspecified phase)
0.6916	Remote Similarity	NPD6661	Clinical (unspecified phase)
0.6914	Remote Similarity	NPD4952	Phase 3
0.6913	Remote Similarity	NPD4037	Approved
0.6913	Remote Similarity	NPD4122	Approved
0.6913	Remote Similarity	NPD32	Approved
0.6913	Remote Similarity	NPD5901	Discontinued
0.6913	Remote Similarity	NPD4038	Approved
0.6913	Remote Similarity	NPD4034	Approved
0.6913	Remote Similarity	NPD4036	Approved
0.6913	Remote Similarity	NPD4033	Approved
0.6913	Remote Similarity	NPD6987	Phase 1
0.6913	Remote Similarity	NPD4039	Approved
0.6913	Remote Similarity	NPD3947	Discontinued
0.6913	Remote Similarity	NPD31	Approved
0.6913	Remote Similarity	NPD4035	Approved
0.6905	Remote Similarity	NPD8102	Discontinued
0.6905	Remote Similarity	NPD4558	Phase 2
0.6903	Remote Similarity	NPD4899	Clinical (unspecified phase)
0.6898	Remote Similarity	NPD6223	Clinical (unspecified phase)
0.6894	Remote Similarity	NPD3945	Discontinued
0.6889	Remote Similarity	NPD6861	Clinical (unspecified phase)
0.6889	Remote Similarity	NPD5975	Clinical (unspecified phase)
0.6888	Remote Similarity	NPD3925	Approved
0.6886	Remote Similarity	NPD1740	Approved
0.6886	Remote Similarity	NPD1739	Approved
0.6885	Remote Similarity	NPD1867	Approved
0.6883	Remote Similarity	NPD4958	Clinical (unspecified phase)
0.688	Remote Similarity	NPD7927	Clinical (unspecified phase)
0.688	Remote Similarity	NPD5416	Discontinued
0.6872	Remote Similarity	NPD7555	Discontinued
0.687	Remote Similarity	NPD6964	Approved
0.687	Remote Similarity	NPD6963	Approved
0.6866	Remote Similarity	NPD2753	Discontinued
0.6862	Remote Similarity	NPD5850	Phase 3
0.6861	Remote Similarity	NPD6281	Approved
0.686	Remote Similarity	NPD6228	Discontinued
0.6857	Remote Similarity	NPD4885	Approved
0.6857	Remote Similarity	NPD3746	Discontinued
0.6853	Remote Similarity	NPD7452	Approved
0.6853	Remote Similarity	NPD7453	Approved
0.6851	Remote Similarity	NPD5866	Approved
0.6851	Remote Similarity	NPD4852	Phase 2
0.6846	Remote Similarity	NPD4894	Discontinued
0.6844	Remote Similarity	NPD9695	Approved
0.6844	Remote Similarity	NPD1304	Clinical (unspecified phase)
0.6844	Remote Similarity	NPD1038	Approved
0.6842	Remote Similarity	NPD4548	Discontinued
0.684	Remote Similarity	NPD1483	Discontinued
0.6838	Remote Similarity	NPD6172	Clinical (unspecified phase)
0.6835	Remote Similarity	NPD2433	Clinical (unspecified phase)
0.6831	Remote Similarity	NPD4845	Discontinued
0.6829	Remote Similarity	NPD4373	Phase 2
0.6825	Remote Similarity	NPD9705	Discontinued
0.6825	Remote Similarity	NPD6460	Clinical (unspecified phase)
0.6825	Remote Similarity	NPD112	Approved
0.6822	Remote Similarity	NPD7571	Clinical (unspecified phase)
0.6822	Remote Similarity	NPD6872	Clinical (unspecified phase)
0.682	Remote Similarity	NPD7803	Approved
0.682	Remote Similarity	NPD5450	Discontinued
0.682	Remote Similarity	NPD3238	Discontinued
0.6815	Remote Similarity	NPD5805	Approved
0.6812	Remote Similarity	NPD7255	Clinical (unspecified phase)
0.681	Remote Similarity	NPD5601	Phase 2
0.6809	Remote Similarity	NPD7703	Clinical (unspecified phase)
0.6809	Remote Similarity	NPD5475	Discontinued
0.6804	Remote Similarity	NPD6293	Clinical (unspecified phase)
0.6803	Remote Similarity	NPD5559	Phase 2
0.6802	Remote Similarity	NPD2951	Discontinued
0.6795	Remote Similarity	NPD5867	Clinical (unspecified phase)
0.6795	Remote Similarity	NPD6529	Discontinued
0.6778	Remote Similarity	NPD5632	Approved
0.6774	Remote Similarity	NPD7853	Phase 2
0.6772	Remote Similarity	NPD8350	Clinical (unspecified phase)
0.6771	Remote Similarity	NPD6257	Clinical (unspecified phase)
0.6769	Remote Similarity	NPD5999	Phase 2
0.6769	Remote Similarity	NPD4118	Clinical (unspecified phase)
0.6766	Remote Similarity	NPD6204	Clinical (unspecified phase)
0.6765	Remote Similarity	NPD5612	Discontinued
0.6763	Remote Similarity	NPD4923	Phase 1
0.6763	Remote Similarity	NPD4881	Clinical (unspecified phase)
0.6762	Remote Similarity	NPD4328	Approved
0.6759	Remote Similarity	NPD1078	Clinical (unspecified phase)
0.6757	Remote Similarity	NPD7955	Approved
0.6757	Remote Similarity	NPD7956	Approved
0.6756	Remote Similarity	NPD2336	Approved
0.6754	Remote Similarity	NPD1622	Discontinued
0.675	Remote Similarity	NPD7404	Approved
0.6748	Remote Similarity	NPD6962	Phase 2
0.6742	Remote Similarity	NPD5522	Clinical (unspecified phase)
0.674	Remote Similarity	NPD6491	Clinical (unspecified phase)
0.6737	Remote Similarity	NPD5939	Approved
0.6737	Remote Similarity	NPD5936	Approved
0.6736	Remote Similarity	NPD3440	Clinical (unspecified phase)
0.6732	Remote Similarity	NPD8358	Approved
0.6729	Remote Similarity	NPD2782	Approved
0.6729	Remote Similarity	NPD2780	Approved
0.6726	Remote Similarity	NPD4372	Phase 1
0.6725	Remote Similarity	NPD4987	Clinical (unspecified phase)
0.6724	Remote Similarity	NPD2121	Clinical (unspecified phase)
0.6723	Remote Similarity	NPD4506	Discontinued
0.6722	Remote Similarity	NPD7180	Phase 3
0.6719	Remote Similarity	NPD6230	Discontinued
0.6718	Remote Similarity	NPD6456	Discontinued
0.6716	Remote Similarity	NPD3217	Phase 2
0.6712	Remote Similarity	NPD3607	Clinical (unspecified phase)
0.6712	Remote Similarity	NPD5083	Clinical (unspecified phase)
0.6711	Remote Similarity	NPD5896	Clinical (unspecified phase)
0.6709	Remote Similarity	NPD6657	Clinical (unspecified phase)
0.6707	Remote Similarity	NPD5861	Clinical (unspecified phase)

Bioactivity similarity: Similar Natural Products in NPASS

Bioactivity similarity was calculated based on bioactivity descriptors of compounds. The bioactivity descriptors were calculated by a recently developed AI algorithm Chemical Checker (CC) [Nature Biotechnology, 38:1087–1096, 2020; Nature Communications, 12:3932, 2021], which evaluated bioactivity similarities at five levels:
☉ A: chemistry similarity;
☉ B: biological targets similarity;
☉ C: networks similarity;
☉ D: cell-based bioactivity similarity;
☉ E: similarity based on clinical data.

Those 5 categories of CC bioactivity descriptors were calculated and then subjected to manifold projection using UMAP algorithm, to project all NPs on a 2-Dimensional space. The current NP was highlighted with a small circle in the 2-D map. Below figures: left-to-right, A-to-E.

A: chemistry similarity

B: biological targets similarity

C: networks similarity

D: cell-based bioactivity similarity

E: similarity based on clinical data