NPASS Compound

Structure

NPC473449 OpenBabel07101718322D 35 41 0 0 1 0 0 0 0 0999 V2000 -2.5024 -2.3716 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9134 -2.0555 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6780 -0.0579 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7292 -1.9201 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1883 0.2658 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8053 1.1719 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1883 1.2400 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4819 0.8461 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3446 -0.2214 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1848 0.7489 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3446 1.7271 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5380 0.0972 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1261 0.2658 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7176 -1.1956 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5009 0.2658 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2410 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9698 -0.2214 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.1261 -1.6827 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.5009 1.2400 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9175 -0.3258 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8135 0.2658 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6766 -1.1719 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9698 -1.1956 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.6572 -0.2214 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6205 -0.4230 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8135 1.2400 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3532 -1.4977 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8135 -1.6827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7176 -0.2214 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.6572 1.7271 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -1.9737 -1.0747 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -0.9698 1.7271 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.4260 -2.4692 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.6572 -1.1956 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 1 28 1 0 0 0 0 2 28 1 0 0 0 0 4 31 1 0 0 0 0 5 7 2 0 0 0 0 5 9 1 0 0 0 0 6 8 2 0 0 0 0 6 10 1 0 0 0 0 7 11 1 0 0 0 0 8 12 1 0 0 0 0 9 15 2 0 0 0 0 10 16 2 0 0 0 0 11 19 2 0 0 0 0 12 20 2 0 0 0 0 13 29 1 0 0 0 0 14 29 1 0 0 0 0 15 19 1 0 0 0 0 15 24 1 0 0 0 0 16 20 1 0 0 0 0 16 25 1 0 0 0 0 17 13 1 1 0 0 0 17 21 1 0 0 0 0 17 23 1 0 0 0 0 18 14 1 6 0 0 0 18 22 1 0 0 0 0 18 23 1 0 0 0 0 19 30 1 0 0 0 0 20 31 1 0 0 0 0 21 24 2 0 0 0 0 21 26 1 0 0 0 0 22 25 2 0 0 0 0 22 27 1 0 0 0 0 23 28 1 6 0 0 0 24 34 1 0 0 0 0 25 35 1 0 0 0 0 26 30 2 0 0 0 0 26 32 1 0 0 0 0 27 31 1 0 0 0 0 27 33 2 0 0 0 0 28 34 1 0 0 0 0 29 3 1 1 0 0 0 29 35 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	468.2
Volume:	481.035
LogP:	6.345
LogD:	4.307
LogS:	-4.572
# Rotatable Bonds:	0
TPSA:	73.32
# H-Bond Aceptor:	6
# H-Bond Donor:	1
# Rings:	7
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.395
Synthetic Accessibility Score:	4.995
Fsp3:	0.379
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.966
MDCK Permeability:	2.358665551582817e-05
Pgp-inhibitor:	0.97
Pgp-substrate:	0.014
Human Intestinal Absorption (HIA):	0.021
20% Bioavailability (F20%):	0.005
30% Bioavailability (F30%):	0.089

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.069
Plasma Protein Binding (PPB):	99.09659576416016%
Volume Distribution (VD):	0.338
Pgp-substrate:	0.7212817668914795%

ADMET: Metabolism

CYP1A2-inhibitor:	0.232
CYP1A2-substrate:	0.964
CYP2C19-inhibitor:	0.577
CYP2C19-substrate:	0.894
CYP2C9-inhibitor:	0.917
CYP2C9-substrate:	0.941
CYP2D6-inhibitor:	0.131
CYP2D6-substrate:	0.065
CYP3A4-inhibitor:	0.645
CYP3A4-substrate:	0.916

ADMET: Excretion

Clearance (CL):	3.836
Half-life (T1/2):	0.114

ADMET: Toxicity

hERG Blockers:	0.463
Human Hepatotoxicity (H-HT):	0.957
Drug-inuced Liver Injury (DILI):	0.974
AMES Toxicity:	0.19
Rat Oral Acute Toxicity:	0.958
Maximum Recommended Daily Dose:	0.945
Skin Sensitization:	0.047
Carcinogencity:	0.769
Eye Corrosion:	0.003
Eye Irritation:	0.02
Respiratory Toxicity:	0.887

Download Data

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

Natural Product: NPC473449

Natural Product ID:	NPC473449
*Common Name:**	TWTOZAQFMDPSKK-LCAWQGBYSA-N
IUPAC Name:	n.a.
Synonyms:	18-Demethylparaensidimerin C
Standard InCHIKey:	TWTOZAQFMDPSKK-LCAWQGBYSA-N
Standard InCHI:	InChI=1S/C29H28N2O4/c1-28(2)23-17(21-24(34-28)15-9-5-7-11-19(15)30-26(21)32)13-29(3)14-18(23)22-25(35-29)16-10-6-8-12-20(16)31(4)27(22)33/h5-12,17-18,23H,13-14H2,1-4H3,(H,30,32)/t17-,18+,23-,29-/m1/s1
SMILES:	Oc1nc2ccccc2c2c1[C@H]1C[C@@]3(C)Oc4c([C@@H]([C@@H]1C(O2)(C)C)C3)c(=O)n(c1c4cccc1)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL436835
PubChem CID:	23642604
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0001253] Quinolines and derivatives [CHEMONTID:0000056] Quinolones and derivatives [CHEMONTID:0001291] Pyranoquinolines

*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
NPO21390	Zanthoxylum integrifoliolum	Species	Rutaceae	Eukaryota	fruit	Lanyu Island, Taitung County, Taiwan	n.a.	PMID[10395498]
NPO21390	Zanthoxylum integrifoliolum	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17822293]
NPO21390	Zanthoxylum integrifoliolum	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO21390	Zanthoxylum integrifoliolum	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	1

Activity Type	# Activity
Cell Line	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT2740	Cell Line	Neutrophils		IC50	>	100000.0	nM	PMID[558700]

☑ 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 NPC473449 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	530
0.1-0.2	2285
0.2-0.3	9100
0.3-0.4	8447
0.4-0.5	10150
0.5-0.6	10221
0.6-0.7	1669
0.7-0.8	280
0.8-0.85	11
0.85-0.9	2
0.9-0.95	0
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.8241	Intermediate Similarity	NPC469439
0.7981	Intermediate Similarity	NPC470931
0.7962	Intermediate Similarity	NPC469440
0.7889	Intermediate Similarity	NPC288943
0.7761	Intermediate Similarity	NPC283152
0.7736	Intermediate Similarity	NPC11017
0.7718	Intermediate Similarity	NPC66083
0.7671	Intermediate Similarity	NPC264176
0.7668	Intermediate Similarity	NPC128115
0.7659	Intermediate Similarity	NPC62069
0.7656	Intermediate Similarity	NPC280964
0.7656	Intermediate Similarity	NPC141915
0.7656	Intermediate Similarity	NPC114335
0.7611	Intermediate Similarity	NPC97746
0.7593	Intermediate Similarity	NPC137929
0.7593	Intermediate Similarity	NPC164374
0.7585	Intermediate Similarity	NPC61350
0.7547	Intermediate Similarity	NPC473053
0.7536	Intermediate Similarity	NPC279401
0.7536	Intermediate Similarity	NPC79293
0.7533	Intermediate Similarity	NPC21638
0.7525	Intermediate Similarity	NPC307640
0.7524	Intermediate Similarity	NPC469390
0.75	Intermediate Similarity	NPC189079
0.7479	Intermediate Similarity	NPC131486
0.7479	Intermediate Similarity	NPC472589
0.7469	Intermediate Similarity	NPC244543
0.7469	Intermediate Similarity	NPC472588
0.7458	Intermediate Similarity	NPC67401
0.7458	Intermediate Similarity	NPC133609
0.7447	Intermediate Similarity	NPC475816
0.7446	Intermediate Similarity	NPC201508
0.7442	Intermediate Similarity	NPC280714
0.7426	Intermediate Similarity	NPC188400
0.7426	Intermediate Similarity	NPC15406
0.7421	Intermediate Similarity	NPC470020
0.7419	Intermediate Similarity	NPC295898
0.7415	Intermediate Similarity	NPC99891
0.7399	Intermediate Similarity	NPC316181
0.7399	Intermediate Similarity	NPC151781
0.7399	Intermediate Similarity	NPC74562
0.7397	Intermediate Similarity	NPC472111
0.7389	Intermediate Similarity	NPC298436
0.7382	Intermediate Similarity	NPC255800
0.7382	Intermediate Similarity	NPC329631
0.7382	Intermediate Similarity	NPC473105
0.7382	Intermediate Similarity	NPC96584
0.7373	Intermediate Similarity	NPC267423
0.7371	Intermediate Similarity	NPC289786
0.7359	Intermediate Similarity	NPC66777
0.7359	Intermediate Similarity	NPC471762
0.7347	Intermediate Similarity	NPC129897
0.7347	Intermediate Similarity	NPC284685
0.7345	Intermediate Similarity	NPC303658
0.7339	Intermediate Similarity	NPC88923
0.7339	Intermediate Similarity	NPC233334
0.7339	Intermediate Similarity	NPC291535
0.7339	Intermediate Similarity	NPC475112
0.7339	Intermediate Similarity	NPC475085
0.7339	Intermediate Similarity	NPC474192
0.7339	Intermediate Similarity	NPC315634
0.7339	Intermediate Similarity	NPC100734
0.7339	Intermediate Similarity	NPC475720
0.7317	Intermediate Similarity	NPC191489
0.7314	Intermediate Similarity	NPC302807
0.7301	Intermediate Similarity	NPC305984
0.7285	Intermediate Similarity	NPC193238
0.7284	Intermediate Similarity	NPC194740
0.7284	Intermediate Similarity	NPC476997
0.7281	Intermediate Similarity	NPC472099
0.7277	Intermediate Similarity	NPC90875
0.7269	Intermediate Similarity	NPC473822
0.7265	Intermediate Similarity	NPC269367
0.7264	Intermediate Similarity	NPC183805
0.726	Intermediate Similarity	NPC15987
0.7254	Intermediate Similarity	NPC329982
0.7253	Intermediate Similarity	NPC476998
0.7253	Intermediate Similarity	NPC24019
0.7253	Intermediate Similarity	NPC476996
0.725	Intermediate Similarity	NPC208522
0.7249	Intermediate Similarity	NPC477532
0.7243	Intermediate Similarity	NPC183537
0.7241	Intermediate Similarity	NPC157931
0.722	Intermediate Similarity	NPC174758
0.7217	Intermediate Similarity	NPC122463
0.7217	Intermediate Similarity	NPC220851
0.7212	Intermediate Similarity	NPC16066
0.721	Intermediate Similarity	NPC311906
0.721	Intermediate Similarity	NPC476994
0.7209	Intermediate Similarity	NPC471825
0.7204	Intermediate Similarity	NPC42591
0.72	Intermediate Similarity	NPC202605
0.72	Intermediate Similarity	NPC472098
0.72	Intermediate Similarity	NPC112206
0.72	Intermediate Similarity	NPC48353
0.7198	Intermediate Similarity	NPC200888
0.7197	Intermediate Similarity	NPC210296
0.7189	Intermediate Similarity	NPC224928
0.7188	Intermediate Similarity	NPC471304
0.7186	Intermediate Similarity	NPC322482
0.7185	Intermediate Similarity	NPC474183
0.7185	Intermediate Similarity	NPC470784
0.7182	Intermediate Similarity	NPC66815
0.7179	Intermediate Similarity	NPC209174
0.7172	Intermediate Similarity	NPC77878
0.7162	Intermediate Similarity	NPC304183
0.7162	Intermediate Similarity	NPC476106
0.7156	Intermediate Similarity	NPC220337
0.7156	Intermediate Similarity	NPC320394
0.7154	Intermediate Similarity	NPC472435
0.7149	Intermediate Similarity	NPC477531
0.7149	Intermediate Similarity	NPC316065
0.7149	Intermediate Similarity	NPC217176
0.7149	Intermediate Similarity	NPC289905
0.7143	Intermediate Similarity	NPC6786
0.7143	Intermediate Similarity	NPC476995
0.7137	Intermediate Similarity	NPC252251
0.713	Intermediate Similarity	NPC53344
0.713	Intermediate Similarity	NPC477533
0.7126	Intermediate Similarity	NPC318068
0.7125	Intermediate Similarity	NPC119134
0.7124	Intermediate Similarity	NPC470018
0.7118	Intermediate Similarity	NPC473041
0.7117	Intermediate Similarity	NPC264166
0.7117	Intermediate Similarity	NPC274291
0.7117	Intermediate Similarity	NPC165349
0.7117	Intermediate Similarity	NPC329708
0.7117	Intermediate Similarity	NPC118832
0.7117	Intermediate Similarity	NPC47059
0.7114	Intermediate Similarity	NPC26850
0.7113	Intermediate Similarity	NPC470785
0.7112	Intermediate Similarity	NPC205372
0.7107	Intermediate Similarity	NPC78609
0.7105	Intermediate Similarity	NPC30570
0.7105	Intermediate Similarity	NPC152768
0.7105	Intermediate Similarity	NPC148183
0.7102	Intermediate Similarity	NPC137353
0.71	Intermediate Similarity	NPC198503
0.7098	Intermediate Similarity	NPC475910
0.7098	Intermediate Similarity	NPC82548
0.7097	Intermediate Similarity	NPC43787
0.7097	Intermediate Similarity	NPC205934
0.7094	Intermediate Similarity	NPC74575
0.7093	Intermediate Similarity	NPC236668
0.7092	Intermediate Similarity	NPC132385
0.7089	Intermediate Similarity	NPC194040
0.7083	Intermediate Similarity	NPC41501
0.708	Intermediate Similarity	NPC87413
0.7078	Intermediate Similarity	NPC72211
0.7072	Intermediate Similarity	NPC53144
0.7072	Intermediate Similarity	NPC317572
0.7071	Intermediate Similarity	NPC184680
0.7069	Intermediate Similarity	NPC280272
0.7069	Intermediate Similarity	NPC210434
0.7068	Intermediate Similarity	NPC472436
0.7067	Intermediate Similarity	NPC201697
0.7067	Intermediate Similarity	NPC174672
0.7064	Intermediate Similarity	NPC70259
0.7061	Intermediate Similarity	NPC146976
0.7061	Intermediate Similarity	NPC237740
0.7059	Intermediate Similarity	NPC253675
0.7056	Intermediate Similarity	NPC174049
0.7056	Intermediate Similarity	NPC174760
0.7056	Intermediate Similarity	NPC150239
0.7054	Intermediate Similarity	NPC475835
0.7051	Intermediate Similarity	NPC45850
0.7048	Intermediate Similarity	NPC305542
0.7046	Intermediate Similarity	NPC49547
0.7043	Intermediate Similarity	NPC469594
0.7043	Intermediate Similarity	NPC96321
0.704	Intermediate Similarity	NPC36229
0.704	Intermediate Similarity	NPC16452
0.704	Intermediate Similarity	NPC476581
0.7037	Intermediate Similarity	NPC472434
0.7037	Intermediate Similarity	NPC124313
0.7035	Intermediate Similarity	NPC290689
0.7034	Intermediate Similarity	NPC469792
0.7032	Intermediate Similarity	NPC70956
0.7032	Intermediate Similarity	NPC243834
0.7031	Intermediate Similarity	NPC330009
0.7031	Intermediate Similarity	NPC274982
0.7029	Intermediate Similarity	NPC477549
0.7029	Intermediate Similarity	NPC473187
0.7029	Intermediate Similarity	NPC108342
0.7026	Intermediate Similarity	NPC280799
0.7025	Intermediate Similarity	NPC84164
0.7025	Intermediate Similarity	NPC207283
0.7021	Intermediate Similarity	NPC478078
0.702	Intermediate Similarity	NPC270515
0.7018	Intermediate Similarity	NPC30749
0.7016	Intermediate Similarity	NPC303374
0.7014	Intermediate Similarity	NPC329747
0.7008	Intermediate Similarity	NPC58209
0.7004	Intermediate Similarity	NPC476999
0.7	Intermediate Similarity	NPC182907
0.7	Intermediate Similarity	NPC234933
0.7	Intermediate Similarity	NPC189903
0.6996	Remote Similarity	NPC223427
0.6996	Remote Similarity	NPC162484
0.6996	Remote Similarity	NPC160100

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 NPC473449 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	340
0.1-0.2	633
0.2-0.3	896
0.3-0.4	1676
0.4-0.5	2710
0.5-0.6	2174
0.6-0.7	640
0.7-0.8	79
0.8-0.85	2
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.7738	Intermediate Similarity	NPD7395	Discontinued
0.7721	Intermediate Similarity	NPD4305	Clinical (unspecified phase)
0.7712	Intermediate Similarity	NPD6525	Clinical (unspecified phase)
0.7685	Intermediate Similarity	NPD5429	Discontinued
0.7655	Intermediate Similarity	NPD7426	Phase 1
0.7639	Intermediate Similarity	NPD7417	Discontinued
0.76	Intermediate Similarity	NPD6824	Clinical (unspecified phase)
0.7597	Intermediate Similarity	NPD7025	Clinical (unspecified phase)
0.7533	Intermediate Similarity	NPD3925	Approved
0.7532	Intermediate Similarity	NPD6716	Phase 1
0.7523	Intermediate Similarity	NPD7222	Phase 2
0.7512	Intermediate Similarity	NPD3946	Clinical (unspecified phase)
0.7511	Intermediate Similarity	NPD7069	Discontinued
0.7489	Intermediate Similarity	NPD2916	Discontinued
0.7478	Intermediate Similarity	NPD7589	Clinical (unspecified phase)
0.7466	Intermediate Similarity	NPD6567	Clinical (unspecified phase)
0.7465	Intermediate Similarity	NPD6550	Discontinued
0.7465	Intermediate Similarity	NPD5512	Phase 3
0.7447	Intermediate Similarity	NPD8016	Phase 3
0.7447	Intermediate Similarity	NPD8017	Clinical (unspecified phase)
0.7444	Intermediate Similarity	NPD5417	Clinical (unspecified phase)
0.7444	Intermediate Similarity	NPD4897	Phase 2
0.7444	Intermediate Similarity	NPD7538	Clinical (unspecified phase)
0.744	Intermediate Similarity	NPD5522	Clinical (unspecified phase)
0.7435	Intermediate Similarity	NPD7710	Clinical (unspecified phase)
0.7424	Intermediate Similarity	NPD3263	Phase 3
0.7418	Intermediate Similarity	NPD6861	Clinical (unspecified phase)
0.7414	Intermediate Similarity	NPD7797	Approved
0.7414	Intermediate Similarity	NPD7796	Approved
0.7411	Intermediate Similarity	NPD2433	Clinical (unspecified phase)
0.7382	Intermediate Similarity	NPD6741	Clinical (unspecified phase)
0.738	Intermediate Similarity	NPD6247	Clinical (unspecified phase)
0.7377	Intermediate Similarity	NPD8091	Phase 3
0.7364	Intermediate Similarity	NPD5488	Discontinued
0.7364	Intermediate Similarity	NPD8359	Phase 2
0.7347	Intermediate Similarity	NPD7955	Approved
0.7347	Intermediate Similarity	NPD7956	Approved
0.7339	Intermediate Similarity	NPD7803	Approved
0.733	Intermediate Similarity	NPD7671	Approved
0.733	Intermediate Similarity	NPD7672	Approved
0.7325	Intermediate Similarity	NPD5507	Approved
0.7325	Intermediate Similarity	NPD5506	Approved
0.7317	Intermediate Similarity	NPD7708	Approved
0.7308	Intermediate Similarity	NPD4204	Approved
0.7308	Intermediate Similarity	NPD4203	Approved
0.7285	Intermediate Similarity	NPD7453	Approved
0.7285	Intermediate Similarity	NPD7452	Approved
0.7265	Intermediate Similarity	NPD4900	Clinical (unspecified phase)
0.7256	Intermediate Similarity	NPD4418	Discontinued
0.7241	Intermediate Similarity	NPD7268	Clinical (unspecified phase)
0.724	Intermediate Similarity	NPD4901	Clinical (unspecified phase)
0.724	Intermediate Similarity	NPD5530	Phase 1
0.7238	Intermediate Similarity	NPD5083	Clinical (unspecified phase)
0.7234	Intermediate Similarity	NPD6494	Phase 2
0.7232	Intermediate Similarity	NPD5416	Discontinued
0.7227	Intermediate Similarity	NPD6991	Approved
0.7222	Intermediate Similarity	NPD6962	Phase 2
0.7212	Intermediate Similarity	NPD5293	Phase 2
0.7209	Intermediate Similarity	NPD6361	Phase 2
0.7184	Intermediate Similarity	NPD8463	Approved
0.7183	Intermediate Similarity	NPD6608	Clinical (unspecified phase)
0.7176	Intermediate Similarity	NPD6491	Clinical (unspecified phase)
0.7176	Intermediate Similarity	NPD6590	Discontinued
0.7163	Intermediate Similarity	NPD6569	Phase 2
0.7161	Intermediate Similarity	NPD4373	Phase 2
0.716	Intermediate Similarity	NPD8102	Discontinued
0.7156	Intermediate Similarity	NPD4502	Phase 2
0.7156	Intermediate Similarity	NPD7889	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD7859	Phase 2
0.7131	Intermediate Similarity	NPD6964	Approved
0.7131	Intermediate Similarity	NPD6963	Approved
0.7125	Intermediate Similarity	NPD6790	Phase 1
0.7119	Intermediate Similarity	NPD4885	Approved
0.7117	Intermediate Similarity	NPD4036	Approved
0.7117	Intermediate Similarity	NPD4033	Approved
0.7117	Intermediate Similarity	NPD4037	Approved
0.7117	Intermediate Similarity	NPD4035	Approved
0.7117	Intermediate Similarity	NPD31	Approved
0.7117	Intermediate Similarity	NPD4122	Approved
0.7117	Intermediate Similarity	NPD4034	Approved
0.7117	Intermediate Similarity	NPD4038	Approved
0.7117	Intermediate Similarity	NPD32	Approved
0.7117	Intermediate Similarity	NPD4039	Approved
0.7106	Intermediate Similarity	NPD4952	Phase 3
0.7087	Intermediate Similarity	NPD3258	Approved
0.7081	Intermediate Similarity	NPD6159	Phase 2
0.7069	Intermediate Similarity	NPD2285	Clinical (unspecified phase)
0.7046	Intermediate Similarity	NPD7031	Phase 1
0.7045	Intermediate Similarity	NPD6874	Approved
0.7042	Intermediate Similarity	NPD4889	Approved
0.7033	Intermediate Similarity	NPD6503	Clinical (unspecified phase)
0.7025	Intermediate Similarity	NPD1483	Discontinued
0.7023	Intermediate Similarity	NPD4334	Discontinued
0.7016	Intermediate Similarity	NPD8246	Approved
0.7016	Intermediate Similarity	NPD8247	Approved
0.7013	Intermediate Similarity	NPD6974	Phase 3
0.7004	Intermediate Similarity	NPD6220	Phase 3
0.7004	Intermediate Similarity	NPD1505	Phase 2
0.6987	Remote Similarity	NPD2951	Discontinued
0.6982	Remote Similarity	NPD6592	Clinical (unspecified phase)
0.6981	Remote Similarity	NPD7414	Clinical (unspecified phase)
0.6979	Remote Similarity	NPD5640	Discontinued
0.6976	Remote Similarity	NPD4926	Clinical (unspecified phase)
0.6972	Remote Similarity	NPD4551	Phase 2
0.697	Remote Similarity	NPD8405	Clinical (unspecified phase)
0.697	Remote Similarity	NPD6568	Discontinued
0.6969	Remote Similarity	NPD7673	Phase 3
0.6967	Remote Similarity	NPD3920	Phase 2
0.696	Remote Similarity	NPD648	Clinical (unspecified phase)
0.6955	Remote Similarity	NPD6769	Clinical (unspecified phase)
0.6955	Remote Similarity	NPD6988	Phase 1
0.6947	Remote Similarity	NPD7467	Discontinued
0.6946	Remote Similarity	NPD5040	Clinical (unspecified phase)
0.6943	Remote Similarity	NPD3243	Approved
0.6942	Remote Similarity	NPD7886	Phase 2
0.6942	Remote Similarity	NPD7885	Phase 2
0.694	Remote Similarity	NPD6955	Clinical (unspecified phase)
0.6933	Remote Similarity	NPD7174	Clinical (unspecified phase)
0.6933	Remote Similarity	NPD3507	Phase 2
0.6929	Remote Similarity	NPD5805	Approved
0.6926	Remote Similarity	NPD4989	Phase 2
0.6923	Remote Similarity	NPD7777	Approved
0.6923	Remote Similarity	NPD7778	Approved
0.6923	Remote Similarity	NPD53	Approved
0.6923	Remote Similarity	NPD4724	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD6995	Phase 1
0.692	Remote Similarity	NPD7654	Discontinued
0.692	Remote Similarity	NPD5014	Discontinued
0.6919	Remote Similarity	NPD5521	Clinical (unspecified phase)
0.6913	Remote Similarity	NPD3257	Approved
0.691	Remote Similarity	NPD7180	Phase 3
0.691	Remote Similarity	NPD6242	Discontinued
0.6907	Remote Similarity	NPD7674	Phase 3
0.6907	Remote Similarity	NPD7676	Clinical (unspecified phase)
0.6907	Remote Similarity	NPD7675	Phase 3
0.6906	Remote Similarity	NPD7566	Clinical (unspecified phase)
0.6897	Remote Similarity	NPD6198	Phase 1
0.6897	Remote Similarity	NPD8109	Clinical (unspecified phase)
0.6892	Remote Similarity	NPD4118	Clinical (unspecified phase)
0.6892	Remote Similarity	NPD3837	Clinical (unspecified phase)
0.6891	Remote Similarity	NPD5801	Clinical (unspecified phase)
0.6888	Remote Similarity	NPD7853	Phase 2
0.6887	Remote Similarity	NPD5900	Clinical (unspecified phase)
0.6887	Remote Similarity	NPD1503	Clinical (unspecified phase)
0.6886	Remote Similarity	NPD4997	Clinical (unspecified phase)
0.6884	Remote Similarity	NPD6344	Clinical (unspecified phase)
0.6883	Remote Similarity	NPD8350	Clinical (unspecified phase)
0.6881	Remote Similarity	NPD3785	Clinical (unspecified phase)
0.6878	Remote Similarity	NPD4328	Approved
0.6878	Remote Similarity	NPD3259	Approved
0.6875	Remote Similarity	NPD7558	Phase 2
0.6872	Remote Similarity	NPD6376	Discontinued
0.6872	Remote Similarity	NPD5658	Approved
0.687	Remote Similarity	NPD7571	Clinical (unspecified phase)
0.6864	Remote Similarity	NPD6246	Approved
0.6864	Remote Similarity	NPD3810	Clinical (unspecified phase)
0.6861	Remote Similarity	NPD5497	Clinical (unspecified phase)
0.6861	Remote Similarity	NPD4500	Approved
0.6861	Remote Similarity	NPD4396	Clinical (unspecified phase)
0.6861	Remote Similarity	NPD4501	Approved
0.6856	Remote Similarity	NPD7703	Clinical (unspecified phase)
0.6855	Remote Similarity	NPD8101	Phase 3
0.6853	Remote Similarity	NPD7823	Clinical (unspecified phase)
0.6849	Remote Similarity	NPD4315	Phase 2
0.6849	Remote Similarity	NPD3921	Approved
0.6849	Remote Similarity	NPD3924	Approved
0.6849	Remote Similarity	NPD4372	Phase 1
0.6849	Remote Similarity	NPD3922	Approved
0.6849	Remote Similarity	NPD3923	Approved
0.6848	Remote Similarity	NPD8364	Approved
0.6848	Remote Similarity	NPD8363	Approved
0.6844	Remote Similarity	NPD7064	Clinical (unspecified phase)
0.6844	Remote Similarity	NPD5513	Phase 2
0.6844	Remote Similarity	NPD8460	Approved
0.6844	Remote Similarity	NPD8459	Approved
0.6842	Remote Similarity	NPD4437	Phase 3
0.6842	Remote Similarity	NPD6276	Discontinued
0.684	Remote Similarity	NPD6641	Approved
0.684	Remote Similarity	NPD6642	Approved
0.6838	Remote Similarity	NPD5930	Phase 3
0.6828	Remote Similarity	NPD7263	Phase 2
0.6826	Remote Similarity	NPD5866	Approved
0.6826	Remote Similarity	NPD3816	Phase 1
0.6826	Remote Similarity	NPD3815	Phase 1
0.6824	Remote Similarity	NPD5632	Approved
0.6822	Remote Similarity	NPD7548	Discontinued
0.6822	Remote Similarity	NPD3386	Phase 2
0.682	Remote Similarity	NPD8052	Clinical (unspecified phase)
0.6816	Remote Similarity	NPD6517	Phase 3
0.6809	Remote Similarity	NPD4923	Phase 1
0.6809	Remote Similarity	NPD7556	Discontinued
0.6808	Remote Similarity	NPD5398	Clinical (unspecified phase)
0.6807	Remote Similarity	NPD7994	Phase 2
0.6802	Remote Similarity	NPD6206	Phase 1
0.6802	Remote Similarity	NPD5003	Discontinued
0.6795	Remote Similarity	NPD8365	Clinical (unspecified phase)
0.6789	Remote Similarity	NPD6965	Clinical (unspecified phase)
0.6787	Remote Similarity	NPD5482	Discontinued
0.6786	Remote Similarity	NPD8255	Phase 2
0.6784	Remote Similarity	NPD3003	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