NPASS Compound

Structure

NPC188400 OpenBabel07101718282D 23 26 0 0 1 0 0 0 0 0999 V2000 -7.8793 -0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.5132 1.0570 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9511 -3.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -1.6180 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5878 -0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5491 -1.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5491 0.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.1472 -1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9511 -1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6831 -1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6831 -0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4152 -1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4152 -0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.1472 -0.3090 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.8171 -1.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9511 -0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.0132 0.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8171 0.1910 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -7.5132 1.0570 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.8171 -2.8090 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.2812 -1.8090 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.2812 0.1910 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 17 1 0 0 0 0 2 17 1 0 0 0 0 3 20 1 0 0 0 0 4 5 2 0 0 0 0 4 9 1 0 0 0 0 5 21 1 0 0 0 0 6 10 2 0 0 0 0 6 12 1 0 0 0 0 7 11 2 0 0 0 0 7 13 1 0 0 0 0 8 14 1 0 0 0 0 8 22 1 0 0 0 0 9 15 2 0 0 0 0 9 16 1 0 0 0 0 10 11 1 0 0 0 0 10 15 1 0 0 0 0 11 18 1 0 0 0 0 12 13 2 0 0 0 0 12 22 1 0 0 0 0 13 23 1 0 0 0 0 14 17 1 6 0 0 0 14 23 1 0 0 0 0 15 20 1 0 0 0 0 16 18 2 0 0 0 0 16 21 1 0 0 0 0 17 19 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	315.11
Volume:	307.492
LogP:	3.274
LogD:	2.913
LogS:	-3.559
# Rotatable Bonds:	2
TPSA:	73.95
# H-Bond Aceptor:	6
# H-Bond Donor:	1
# Rings:	4
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.784
Synthetic Accessibility Score:	3.535
Fsp3:	0.353
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
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:	-4.876
MDCK Permeability:	1.8138493032893166e-05
Pgp-inhibitor:	0.002
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.016
20% Bioavailability (F20%):	0.002
30% Bioavailability (F30%):	0.001

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.196
Plasma Protein Binding (PPB):	90.60497283935547%
Volume Distribution (VD):	0.486
Pgp-substrate:	7.226681709289551%

ADMET: Metabolism

CYP1A2-inhibitor:	0.963
CYP1A2-substrate:	0.81
CYP2C19-inhibitor:	0.58
CYP2C19-substrate:	0.417
CYP2C9-inhibitor:	0.667
CYP2C9-substrate:	0.738
CYP2D6-inhibitor:	0.612
CYP2D6-substrate:	0.743
CYP3A4-inhibitor:	0.276
CYP3A4-substrate:	0.393

ADMET: Excretion

Clearance (CL):	6.539
Half-life (T1/2):	0.311

ADMET: Toxicity

hERG Blockers:	0.062
Human Hepatotoxicity (H-HT):	0.615
Drug-inuced Liver Injury (DILI):	0.899
AMES Toxicity:	0.126
Rat Oral Acute Toxicity:	0.176
Maximum Recommended Daily Dose:	0.691
Skin Sensitization:	0.249
Carcinogencity:	0.487
Eye Corrosion:	0.003
Eye Irritation:	0.026
Respiratory Toxicity:	0.859

Download Data

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

Natural Product: NPC188400

Natural Product ID:	NPC188400
*Common Name:**	Quinosuaveoline B
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	OXDIHTWLYDWMMZ-CQSZACIVSA-N
Standard InCHI:	InChI=1S/C17H17NO5/c1-17(2,19)14-8-22-12-6-10-11(7-13(12)23-14)18-16-9(4-5-21-16)15(10)20-3/h4-7,14,19H,8H2,1-3H3/t14-/m1/s1
SMILES:	COc1c2cc3OC[C@@H](Oc3cc2nc2c1cco2)C(O)(C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL574554
PubChem CID:	25157869
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0001253] Quinolines and derivatives [CHEMONTID:0002374] Furanoquinolines

*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
NPO20206	Oricia suaveolens	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18950230]
NPO20206	Oricia suaveolens	Species	Rutaceae	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	2

Activity Type	# Activity
NON-MOLECULAR	1
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	56800.0	nM	PMID[518289]
NPT2	Others	Unspecified		IC50	=	14500.0	nM	PMID[518289]

☑ 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 NPC188400 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	526
0.1-0.2	2543
0.2-0.3	11426
0.3-0.4	6286
0.4-0.5	9116
0.5-0.6	11175
0.6-0.7	1369
0.7-0.8	231
0.8-0.85	8
0.85-0.9	11
0.9-0.95	5
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9533	High Similarity	NPC217176
0.9283	High Similarity	NPC58209
0.9231	High Similarity	NPC168922
0.9062	High Similarity	NPC166712
0.9032	High Similarity	NPC97746
0.9022	High Similarity	NPC160100
0.8987	High Similarity	NPC1608
0.8977	High Similarity	NPC298436
0.8964	High Similarity	NPC34770
0.8826	High Similarity	NPC203373
0.8791	High Similarity	NPC16066
0.8701	High Similarity	NPC173250
0.869	High Similarity	NPC208364
0.8605	High Similarity	NPC269367
0.8554	High Similarity	NPC101312
0.8481	Intermediate Similarity	NPC120513
0.8444	Intermediate Similarity	NPC140296
0.8311	Intermediate Similarity	NPC205372
0.8251	Intermediate Similarity	NPC131885
0.8018	Intermediate Similarity	NPC219664
0.7946	Intermediate Similarity	NPC203168
0.7927	Intermediate Similarity	NPC89549
0.7824	Intermediate Similarity	NPC79293
0.7824	Intermediate Similarity	NPC279401
0.7773	Intermediate Similarity	NPC6786
0.7729	Intermediate Similarity	NPC315634
0.7729	Intermediate Similarity	NPC88923
0.7729	Intermediate Similarity	NPC100734
0.7672	Intermediate Similarity	NPC198503
0.7671	Intermediate Similarity	NPC284685
0.7649	Intermediate Similarity	NPC209981
0.7619	Intermediate Similarity	NPC46561
0.757	Intermediate Similarity	NPC191489
0.7554	Intermediate Similarity	NPC150239
0.7554	Intermediate Similarity	NPC469439
0.7531	Intermediate Similarity	NPC119134
0.7468	Intermediate Similarity	NPC247803
0.746	Intermediate Similarity	NPC134637
0.7441	Intermediate Similarity	NPC230683
0.7441	Intermediate Similarity	NPC471978
0.7426	Intermediate Similarity	NPC473449
0.7422	Intermediate Similarity	NPC471979
0.7411	Intermediate Similarity	NPC280714
0.7409	Intermediate Similarity	NPC107123
0.7404	Intermediate Similarity	NPC174760
0.7403	Intermediate Similarity	NPC308137
0.7403	Intermediate Similarity	NPC310211
0.7389	Intermediate Similarity	NPC66815
0.7388	Intermediate Similarity	NPC99891
0.7377	Intermediate Similarity	NPC470785
0.7354	Intermediate Similarity	NPC227824
0.7352	Intermediate Similarity	NPC66083
0.735	Intermediate Similarity	NPC169402
0.7336	Intermediate Similarity	NPC249583
0.7336	Intermediate Similarity	NPC184680
0.7328	Intermediate Similarity	NPC264176
0.7317	Intermediate Similarity	NPC475844
0.7306	Intermediate Similarity	NPC470784
0.7306	Intermediate Similarity	NPC474183
0.7295	Intermediate Similarity	NPC473187
0.7294	Intermediate Similarity	NPC473833
0.7294	Intermediate Similarity	NPC62069
0.7293	Intermediate Similarity	NPC45190
0.7291	Intermediate Similarity	NPC473188
0.7291	Intermediate Similarity	NPC302807
0.7287	Intermediate Similarity	NPC124300
0.7287	Intermediate Similarity	NPC470042
0.7284	Intermediate Similarity	NPC295479
0.7284	Intermediate Similarity	NPC146418
0.7284	Intermediate Similarity	NPC220241
0.7281	Intermediate Similarity	NPC41216
0.728	Intermediate Similarity	NPC179287
0.7266	Intermediate Similarity	NPC282346
0.7265	Intermediate Similarity	NPC116238
0.7258	Intermediate Similarity	NPC291609
0.7257	Intermediate Similarity	NPC128115
0.7254	Intermediate Similarity	NPC253675
0.7253	Intermediate Similarity	NPC116178
0.7244	Intermediate Similarity	NPC13603
0.7237	Intermediate Similarity	NPC199277
0.7237	Intermediate Similarity	NPC135887
0.7229	Intermediate Similarity	NPC148896
0.7229	Intermediate Similarity	NPC471013
0.7229	Intermediate Similarity	NPC180668
0.7222	Intermediate Similarity	NPC473800
0.7222	Intermediate Similarity	NPC67401
0.7222	Intermediate Similarity	NPC217903
0.7215	Intermediate Similarity	NPC208084
0.721	Intermediate Similarity	NPC87413
0.721	Intermediate Similarity	NPC23294
0.7205	Intermediate Similarity	NPC326930
0.7205	Intermediate Similarity	NPC85879
0.7205	Intermediate Similarity	NPC317572
0.7205	Intermediate Similarity	NPC53255
0.7205	Intermediate Similarity	NPC475301
0.72	Intermediate Similarity	NPC310618
0.7198	Intermediate Similarity	NPC215837
0.7191	Intermediate Similarity	NPC146976
0.7189	Intermediate Similarity	NPC15406
0.7188	Intermediate Similarity	NPC129897
0.7184	Intermediate Similarity	NPC90875
0.7183	Intermediate Similarity	NPC10904
0.7179	Intermediate Similarity	NPC472098
0.7171	Intermediate Similarity	NPC328928
0.7167	Intermediate Similarity	NPC314633
0.7167	Intermediate Similarity	NPC303951
0.7161	Intermediate Similarity	NPC3207
0.7155	Intermediate Similarity	NPC280799
0.7154	Intermediate Similarity	NPC183537
0.7154	Intermediate Similarity	NPC77878
0.7149	Intermediate Similarity	NPC321166
0.7149	Intermediate Similarity	NPC236668
0.7149	Intermediate Similarity	NPC204385
0.7137	Intermediate Similarity	NPC303374
0.7137	Intermediate Similarity	NPC21638
0.713	Intermediate Similarity	NPC312872
0.7125	Intermediate Similarity	NPC148124
0.7119	Intermediate Similarity	NPC476997
0.7114	Intermediate Similarity	NPC277351
0.7112	Intermediate Similarity	NPC193238
0.7112	Intermediate Similarity	NPC474595
0.7112	Intermediate Similarity	NPC4687
0.7109	Intermediate Similarity	NPC472589
0.7107	Intermediate Similarity	NPC200888
0.7101	Intermediate Similarity	NPC182853
0.7101	Intermediate Similarity	NPC473822
0.7098	Intermediate Similarity	NPC471015
0.7098	Intermediate Similarity	NPC469390
0.7093	Intermediate Similarity	NPC185197
0.7092	Intermediate Similarity	NPC124313
0.7092	Intermediate Similarity	NPC78609
0.709	Intermediate Similarity	NPC476996
0.709	Intermediate Similarity	NPC476998
0.709	Intermediate Similarity	NPC24019
0.709	Intermediate Similarity	NPC314222
0.709	Intermediate Similarity	NPC196449
0.7083	Intermediate Similarity	NPC118189
0.7083	Intermediate Similarity	NPC99724
0.7082	Intermediate Similarity	NPC86834
0.7082	Intermediate Similarity	NPC210828
0.708	Intermediate Similarity	NPC84164
0.708	Intermediate Similarity	NPC207283
0.7078	Intermediate Similarity	NPC248903
0.7076	Intermediate Similarity	NPC74562
0.7076	Intermediate Similarity	NPC151781
0.7076	Intermediate Similarity	NPC474594
0.7076	Intermediate Similarity	NPC316181
0.7072	Intermediate Similarity	NPC194040
0.707	Intermediate Similarity	NPC472435
0.7069	Intermediate Similarity	NPC300156
0.7069	Intermediate Similarity	NPC472111
0.7069	Intermediate Similarity	NPC472286
0.7069	Intermediate Similarity	NPC472287
0.7068	Intermediate Similarity	NPC475816
0.7068	Intermediate Similarity	NPC41501
0.7064	Intermediate Similarity	NPC283152
0.7049	Intermediate Similarity	NPC246381
0.7049	Intermediate Similarity	NPC194740
0.7049	Intermediate Similarity	NPC476994
0.7043	Intermediate Similarity	NPC318068
0.7042	Intermediate Similarity	NPC54066
0.7042	Intermediate Similarity	NPC472099
0.7039	Intermediate Similarity	NPC198160
0.7039	Intermediate Similarity	NPC321428
0.7037	Intermediate Similarity	NPC26928
0.7033	Intermediate Similarity	NPC233334
0.7031	Intermediate Similarity	NPC472588
0.7029	Intermediate Similarity	NPC87560
0.7028	Intermediate Similarity	NPC166722
0.7021	Intermediate Similarity	NPC314834
0.7012	Intermediate Similarity	NPC329830
0.7012	Intermediate Similarity	NPC76478
0.7009	Intermediate Similarity	NPC39679
0.7008	Intermediate Similarity	NPC473639
0.7008	Intermediate Similarity	NPC270515
0.7004	Intermediate Similarity	NPC268223
0.7004	Intermediate Similarity	NPC172222
0.7004	Intermediate Similarity	NPC473105
0.7	Intermediate Similarity	NPC148409
0.6992	Remote Similarity	NPC474688
0.6988	Remote Similarity	NPC476995
0.6988	Remote Similarity	NPC182907
0.6988	Remote Similarity	NPC189903
0.6988	Remote Similarity	NPC472436
0.6988	Remote Similarity	NPC477589
0.6988	Remote Similarity	NPC477587
0.6987	Remote Similarity	NPC305984
0.6983	Remote Similarity	NPC162484
0.6983	Remote Similarity	NPC469440
0.698	Remote Similarity	NPC274640
0.698	Remote Similarity	NPC165964
0.6979	Remote Similarity	NPC325297
0.6978	Remote Similarity	NPC207620
0.6978	Remote Similarity	NPC45389
0.6972	Remote Similarity	NPC210296
0.6972	Remote Similarity	NPC49672
0.6971	Remote Similarity	NPC225279
0.6969	Remote Similarity	NPC161801
0.6968	Remote Similarity	NPC206201
0.6966	Remote Similarity	NPC53344

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 NPC188400 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	334
0.1-0.2	656
0.2-0.3	1197
0.3-0.4	1921
0.4-0.5	2685
0.5-0.6	1816
0.6-0.7	488
0.7-0.8	53
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
0.7819	Intermediate Similarity	NPD6525	Clinical (unspecified phase)
0.7782	Intermediate Similarity	NPD7025	Clinical (unspecified phase)
0.7729	Intermediate Similarity	NPD7803	Approved
0.7671	Intermediate Similarity	NPD7955	Approved
0.7671	Intermediate Similarity	NPD7956	Approved
0.757	Intermediate Similarity	NPD7708	Approved
0.7511	Intermediate Similarity	NPD4328	Approved
0.749	Intermediate Similarity	NPD6962	Phase 2
0.744	Intermediate Similarity	NPD4926	Clinical (unspecified phase)
0.7436	Intermediate Similarity	NPD3258	Approved
0.74	Intermediate Similarity	NPD7859	Phase 2
0.7382	Intermediate Similarity	NPD2433	Clinical (unspecified phase)
0.7362	Intermediate Similarity	NPD6974	Phase 3
0.7358	Intermediate Similarity	NPD6716	Phase 1
0.7355	Intermediate Similarity	NPD4373	Phase 2
0.7352	Intermediate Similarity	NPD8091	Phase 3
0.7325	Intermediate Similarity	NPD6963	Approved
0.7325	Intermediate Similarity	NPD6964	Approved
0.7287	Intermediate Similarity	NPD1483	Discontinued
0.7284	Intermediate Similarity	NPD6567	Clinical (unspecified phase)
0.728	Intermediate Similarity	NPD3925	Approved
0.7273	Intermediate Similarity	NPD1505	Phase 2
0.7269	Intermediate Similarity	NPD5488	Discontinued
0.7265	Intermediate Similarity	NPD5805	Approved
0.7265	Intermediate Similarity	NPD3257	Approved
0.7247	Intermediate Similarity	NPD7417	Discontinued
0.7231	Intermediate Similarity	NPD4898	Clinical (unspecified phase)
0.7231	Intermediate Similarity	NPD4952	Phase 3
0.7227	Intermediate Similarity	NPD6228	Discontinued
0.7222	Intermediate Similarity	NPD7571	Clinical (unspecified phase)
0.7213	Intermediate Similarity	NPD6494	Phase 2
0.7211	Intermediate Similarity	NPD8102	Discontinued
0.7191	Intermediate Similarity	NPD5417	Clinical (unspecified phase)
0.7177	Intermediate Similarity	NPD6790	Phase 1
0.716	Intermediate Similarity	NPD7589	Clinical (unspecified phase)
0.7155	Intermediate Similarity	NPD5658	Approved
0.7137	Intermediate Similarity	NPD7885	Phase 2
0.7137	Intermediate Similarity	NPD7886	Phase 2
0.7125	Intermediate Similarity	NPD6824	Clinical (unspecified phase)
0.7124	Intermediate Similarity	NPD5512	Phase 3
0.7119	Intermediate Similarity	NPD5293	Phase 2
0.7102	Intermediate Similarity	NPD4885	Approved
0.7102	Intermediate Similarity	NPD7797	Approved
0.7102	Intermediate Similarity	NPD7796	Approved
0.7101	Intermediate Similarity	NPD5632	Approved
0.7071	Intermediate Similarity	NPD2899	Discontinued
0.7064	Intermediate Similarity	NPD5416	Discontinued
0.7047	Intermediate Similarity	NPD5482	Discontinued
0.7046	Intermediate Similarity	NPD4897	Phase 2
0.7037	Intermediate Similarity	NPD7426	Phase 1
0.7037	Intermediate Similarity	NPD5640	Discontinued
0.7034	Intermediate Similarity	NPD5866	Approved
0.7032	Intermediate Similarity	NPD3920	Phase 2
0.7031	Intermediate Similarity	NPD8463	Approved
0.7029	Intermediate Similarity	NPD7395	Discontinued
0.7024	Intermediate Similarity	NPD5483	Clinical (unspecified phase)
0.7016	Intermediate Similarity	NPD7853	Phase 2
0.7013	Intermediate Similarity	NPD2779	Approved
0.6996	Remote Similarity	NPD8359	Phase 2
0.6996	Remote Similarity	NPD3507	Phase 2
0.6982	Remote Similarity	NPD5083	Clinical (unspecified phase)
0.6981	Remote Similarity	NPD5922	Phase 3
0.6975	Remote Similarity	NPD5902	Approved
0.6975	Remote Similarity	NPD4667	Clinical (unspecified phase)
0.6975	Remote Similarity	NPD5903	Approved
0.6971	Remote Similarity	NPD7180	Phase 3
0.6971	Remote Similarity	NPD5930	Phase 3
0.6969	Remote Similarity	NPD3328	Phase 2
0.6967	Remote Similarity	NPD3263	Phase 3
0.6966	Remote Similarity	NPD7222	Phase 2
0.6966	Remote Similarity	NPD5429	Discontinued
0.6963	Remote Similarity	NPD8459	Approved
0.6963	Remote Similarity	NPD8460	Approved
0.6962	Remote Similarity	NPD7069	Discontinued
0.6955	Remote Similarity	NPD7547	Clinical (unspecified phase)
0.693	Remote Similarity	NPD4418	Discontinued
0.6926	Remote Similarity	NPD6247	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD1867	Approved
0.6918	Remote Similarity	NPD7690	Clinical (unspecified phase)
0.6904	Remote Similarity	NPD7538	Clinical (unspecified phase)
0.69	Remote Similarity	NPD6550	Discontinued
0.6892	Remote Similarity	NPD7729	Clinical (unspecified phase)
0.6883	Remote Similarity	NPD2778	Approved
0.6883	Remote Similarity	NPD5022	Discontinued
0.6878	Remote Similarity	NPD648	Clinical (unspecified phase)
0.6877	Remote Similarity	NPD6517	Phase 3
0.6877	Remote Similarity	NPD4875	Phase 3
0.6877	Remote Similarity	NPD8466	Approved
0.6877	Remote Similarity	NPD4876	Phase 3
0.6877	Remote Similarity	NPD8467	Approved
0.6877	Remote Similarity	NPD8465	Approved
0.6872	Remote Similarity	NPD5507	Approved
0.6872	Remote Similarity	NPD5506	Approved
0.687	Remote Similarity	NPD3259	Approved
0.6867	Remote Similarity	NPD7558	Phase 2
0.6865	Remote Similarity	NPD2921	Clinical (unspecified phase)
0.6831	Remote Similarity	NPD8479	Phase 2
0.6822	Remote Similarity	NPD7452	Approved
0.6822	Remote Similarity	NPD7453	Approved
0.6821	Remote Similarity	NPD6745	Discontinued
0.6809	Remote Similarity	NPD3946	Clinical (unspecified phase)
0.6809	Remote Similarity	NPD4369	Phase 2
0.6802	Remote Similarity	NPD7268	Clinical (unspecified phase)
0.6792	Remote Similarity	NPD3945	Discontinued
0.6792	Remote Similarity	NPD5450	Discontinued
0.6783	Remote Similarity	NPD6243	Phase 3
0.6783	Remote Similarity	NPD6244	Phase 3
0.6783	Remote Similarity	NPD6861	Clinical (unspecified phase)
0.678	Remote Similarity	NPD4305	Clinical (unspecified phase)
0.678	Remote Similarity	NPD3003	Approved
0.678	Remote Similarity	NPD4901	Clinical (unspecified phase)
0.6778	Remote Similarity	NPD7703	Clinical (unspecified phase)
0.6777	Remote Similarity	NPD8425	Approved
0.6777	Remote Similarity	NPD3949	Clinical (unspecified phase)
0.6777	Remote Similarity	NPD8426	Approved
0.6776	Remote Similarity	NPD6160	Clinical (unspecified phase)
0.6773	Remote Similarity	NPD2951	Discontinued
0.6769	Remote Similarity	NPD3921	Approved
0.6769	Remote Similarity	NPD3922	Approved
0.6769	Remote Similarity	NPD3924	Approved
0.6769	Remote Similarity	NPD3923	Approved
0.6768	Remote Similarity	NPD6531	Approved
0.6768	Remote Similarity	NPD6530	Approved
0.6762	Remote Similarity	NPD6242	Discontinued
0.676	Remote Similarity	NPD7031	Phase 1
0.6758	Remote Similarity	NPD4724	Clinical (unspecified phase)
0.6757	Remote Similarity	NPD6503	Clinical (unspecified phase)
0.6753	Remote Similarity	NPD8428	Approved
0.6753	Remote Similarity	NPD3217	Phase 2
0.6753	Remote Similarity	NPD8427	Approved
0.6753	Remote Similarity	NPD8429	Approved
0.675	Remote Similarity	NPD3816	Phase 1
0.675	Remote Similarity	NPD3815	Phase 1
0.6747	Remote Similarity	NPD5801	Clinical (unspecified phase)
0.6747	Remote Similarity	NPD5924	Discontinued
0.6745	Remote Similarity	NPD5833	Phase 1
0.6744	Remote Similarity	NPD8350	Clinical (unspecified phase)
0.6742	Remote Similarity	NPD7862	Clinical (unspecified phase)
0.6741	Remote Similarity	NPD4203	Approved
0.6741	Remote Similarity	NPD4204	Approved
0.6738	Remote Similarity	NPD6874	Approved
0.6736	Remote Similarity	NPD4900	Clinical (unspecified phase)
0.6734	Remote Similarity	NPD6553	Clinical (unspecified phase)
0.6733	Remote Similarity	NPD6741	Clinical (unspecified phase)
0.6721	Remote Similarity	NPD3875	Discontinued
0.672	Remote Similarity	NPD1467	Approved
0.672	Remote Similarity	NPD1466	Phase 3
0.672	Remote Similarity	NPD7284	Clinical (unspecified phase)
0.6719	Remote Similarity	NPD6495	Clinical (unspecified phase)
0.6716	Remote Similarity	NPD8364	Approved
0.6716	Remote Similarity	NPD8363	Approved
0.6711	Remote Similarity	NPD6608	Clinical (unspecified phase)
0.6708	Remote Similarity	NPD4989	Phase 2
0.6708	Remote Similarity	NPD683	Approved
0.6707	Remote Similarity	NPD7710	Clinical (unspecified phase)
0.6705	Remote Similarity	NPD5532	Phase 2
0.6705	Remote Similarity	NPD6276	Discontinued
0.6694	Remote Similarity	NPD5070	Clinical (unspecified phase)
0.668	Remote Similarity	NPD5479	Discontinued
0.668	Remote Similarity	NPD4558	Phase 2
0.668	Remote Similarity	NPD7022	Phase 2
0.6667	Remote Similarity	NPD1768	Approved
0.6667	Remote Similarity	NPD5612	Discontinued
0.6667	Remote Similarity	NPD5914	Approved
0.6667	Remote Similarity	NPD4997	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD5857	Phase 3
0.6667	Remote Similarity	NPD1166	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD8365	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD5905	Phase 1
0.6654	Remote Similarity	NPD8255	Phase 2
0.6654	Remote Similarity	NPD7588	Discontinued
0.6654	Remote Similarity	NPD4846	Phase 2
0.6654	Remote Similarity	NPD8101	Phase 3
0.6653	Remote Similarity	NPD3441	Approved
0.6653	Remote Similarity	NPD3442	Approved
0.6653	Remote Similarity	NPD956	Clinical (unspecified phase)
0.6653	Remote Similarity	NPD5519	Discontinued
0.6652	Remote Similarity	NPD5003	Discontinued
0.664	Remote Similarity	NPD2285	Clinical (unspecified phase)
0.6639	Remote Similarity	NPD3326	Clinical (unspecified phase)
0.6638	Remote Similarity	NPD6590	Discontinued
0.6638	Remote Similarity	NPD7255	Clinical (unspecified phase)
0.6626	Remote Similarity	NPD1638	Discovery
0.6626	Remote Similarity	NPD7559	Phase 2
0.6612	Remote Similarity	NPD1926	Approved
0.6612	Remote Similarity	NPD3354	Phase 2
0.6597	Remote Similarity	NPD4035	Approved
0.6597	Remote Similarity	NPD32	Approved
0.6597	Remote Similarity	NPD4036	Approved
0.6597	Remote Similarity	NPD6138	Clinical (unspecified phase)
0.6597	Remote Similarity	NPD4122	Approved
0.6597	Remote Similarity	NPD4037	Approved
0.6597	Remote Similarity	NPD4038	Approved
0.6597	Remote Similarity	NPD4033	Approved
0.6597	Remote Similarity	NPD31	Approved
0.6597	Remote Similarity	NPD4039	Approved
0.6597	Remote Similarity	NPD4034	Approved
0.6594	Remote Similarity	NPD6257	Clinical (unspecified phase)
0.6589	Remote Similarity	NPD7620	Phase 2
0.6588	Remote Similarity	NPD4368	Phase 2

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