NPASS Compound

Structure

NPC246913 OpenBabel07101718322D 37 40 0 0 1 0 0 0 0 0999 V2000 3.4641 -5.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -5.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9282 -5.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.7942 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9282 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.7942 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7226 2.8966 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8698 -0.8226 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2556 2.6887 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2007 -1.5657 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9282 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3917 2.1535 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5608 0.1285 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5646 1.7377 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2226 -1.3578 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 -2.0000 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 2.5981 -4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0827 1.2024 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5827 0.3364 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1045 0.9945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9135 -0.4067 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 -3.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.5981 -3.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.4641 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 -3.5000 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 4.3301 -3.5000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -3.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.9282 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 -4.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 19 1 0 0 0 0 2 19 1 0 0 0 0 3 36 1 0 0 0 0 4 5 2 0 0 0 0 4 6 1 0 0 0 0 5 11 1 0 0 0 0 6 12 2 0 0 0 0 7 9 2 0 0 0 0 7 13 1 0 0 0 0 8 10 2 0 0 0 0 8 14 1 0 0 0 0 9 15 1 0 0 0 0 10 16 1 0 0 0 0 11 20 2 0 0 0 0 12 20 1 0 0 0 0 13 21 2 0 0 0 0 14 22 2 0 0 0 0 15 23 2 0 0 0 0 16 24 2 0 0 0 0 17 20 1 0 0 0 0 18 25 1 0 0 0 0 18 37 1 0 0 0 0 21 22 1 0 0 0 0 21 23 1 0 0 0 0 22 24 1 0 0 0 0 23 25 1 0 0 0 0 24 25 1 0 0 0 0 26 17 1 1 0 0 0 26 29 1 0 0 0 0 26 31 1 0 0 0 0 27 19 1 6 0 0 0 27 28 1 0 0 0 0 27 32 1 0 0 0 0 28 31 2 3 0 0 0 28 33 1 0 0 0 0 29 34 2 0 0 0 0 29 36 1 0 0 0 0 30 32 2 3 0 0 0 30 35 1 0 0 0 0 30 37 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	500.23
Volume:	527.517
LogP:	4.818
LogD:	4.206
LogS:	-4.824
# Rotatable Bonds:	13
TPSA:	93.73
# H-Bond Aceptor:	7
# H-Bond Donor:	2
# Rings:	4
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.424
Synthetic Accessibility Score:	2.997
Fsp3:	0.3
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.912
MDCK Permeability:	0.00014855047629680485
Pgp-inhibitor:	0.985
Pgp-substrate:	0.731
Human Intestinal Absorption (HIA):	0.005
20% Bioavailability (F20%):	0.023
30% Bioavailability (F30%):	0.049

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.518
Plasma Protein Binding (PPB):	96.66651916503906%
Volume Distribution (VD):	0.735
Pgp-substrate:	1.5047794580459595%

ADMET: Metabolism

CYP1A2-inhibitor:	0.084
CYP1A2-substrate:	0.174
CYP2C19-inhibitor:	0.944
CYP2C19-substrate:	0.515
CYP2C9-inhibitor:	0.88
CYP2C9-substrate:	0.18
CYP2D6-inhibitor:	0.895
CYP2D6-substrate:	0.768
CYP3A4-inhibitor:	0.959
CYP3A4-substrate:	0.771

ADMET: Excretion

Clearance (CL):	2.513
Half-life (T1/2):	0.109

ADMET: Toxicity

hERG Blockers:	0.603
Human Hepatotoxicity (H-HT):	0.804
Drug-inuced Liver Injury (DILI):	0.942
AMES Toxicity:	0.715
Rat Oral Acute Toxicity:	0.82
Maximum Recommended Daily Dose:	0.492
Skin Sensitization:	0.041
Carcinogencity:	0.193
Eye Corrosion:	0.003
Eye Irritation:	0.007
Respiratory Toxicity:	0.031

Download Data

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

Natural Product: NPC246913

Natural Product ID:	NPC246913
*Common Name:**	Ixorapeptide I
IUPAC Name:	methyl (2S)-2-[[(2S)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-3-methylbutanoyl]amino]-3-phenylpropanoate
Synonyms:	Ixorapeptide I
Standard InCHIKey:	MOTXJERIRYLGLC-SVBPBHIXSA-N
Standard InCHI:	InChI=1S/C30H32N2O5/c1-19(2)27(28(33)31-26(29(34)36-3)17-20-11-5-4-6-12-20)32-30(35)37-18-25-23-15-9-7-13-21(23)22-14-8-10-16-24(22)25/h4-16,19,25-27H,17-18H2,1-3H3,(H,31,33)(H,32,35)/t26-,27-/m0/s1
SMILES:	CC(C)[C@@H](C(=N[C@@H](Cc1ccccc1)C(=O)OC)O)N=C(O)OCC1c2ccccc2-c2ccccc12
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1288061
PubChem CID:	15484640
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:0000348] Peptides

*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
NPO6876	Ixora coccinea	Species	Rubiaceae	Eukaryota	aerial parts	collected on the campus of Kaohsiung Medical University, Taiwan	2007-Oct	PMID[21106454]
NPO6876	Ixora coccinea	Species	Rubiaceae	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

Activity Type	# Activity
Cell Line	5
NON-MOLECULAR	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT65	Cell Line	HepG2	Homo sapiens	IC50	>	20.0	ug.mL-1	PMID[456132]
NPT1031	Cell Line	Ca9-22	Homo sapiens	IC50	=	20.0	ug.mL-1	PMID[456132]
NPT81	Cell Line	A549	Homo sapiens	IC50	>	20.0	ug.mL-1	PMID[456132]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	>	20.0	ug.mL-1	PMID[456132]
NPT82	Cell Line	MDA-MB-231	Homo sapiens	IC50	>	20.0	ug.mL-1	PMID[456132]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	3.36	ug.mL-1	PMID[456132]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	29.52	ug.mL-1	PMID[456132]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	20.51	ug.mL-1	PMID[456132]

☑ 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 NPC246913 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	111
0.1-0.2	708
0.2-0.3	2114
0.3-0.4	9174
0.4-0.5	22122
0.5-0.6	7469
0.6-0.7	889
0.7-0.8	101
0.8-0.85	8
0.85-0.9	0
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.8321	Intermediate Similarity	NPC4974
0.8062	Intermediate Similarity	NPC310467
0.7984	Intermediate Similarity	NPC169328
0.7926	Intermediate Similarity	NPC210950
0.7926	Intermediate Similarity	NPC199738
0.791	Intermediate Similarity	NPC47667
0.7823	Intermediate Similarity	NPC470274
0.7803	Intermediate Similarity	NPC190663
0.7761	Intermediate Similarity	NPC35996
0.7734	Intermediate Similarity	NPC474584
0.7717	Intermediate Similarity	NPC319579
0.7687	Intermediate Similarity	NPC160493
0.7669	Intermediate Similarity	NPC80150
0.7669	Intermediate Similarity	NPC45777
0.7669	Intermediate Similarity	NPC477061
0.7652	Intermediate Similarity	NPC237420
0.7643	Intermediate Similarity	NPC244866
0.7557	Intermediate Similarity	NPC197470
0.7537	Intermediate Similarity	NPC478016
0.7537	Intermediate Similarity	NPC478014
0.7537	Intermediate Similarity	NPC478015
0.748	Intermediate Similarity	NPC12730
0.7402	Intermediate Similarity	NPC327481
0.7397	Intermediate Similarity	NPC161069
0.7388	Intermediate Similarity	NPC314992
0.7357	Intermediate Similarity	NPC473322
0.7357	Intermediate Similarity	NPC296712
0.7338	Intermediate Similarity	NPC477937
0.7305	Intermediate Similarity	NPC478147
0.7302	Intermediate Similarity	NPC164859
0.7297	Intermediate Similarity	NPC473922
0.7266	Intermediate Similarity	NPC191215
0.7266	Intermediate Similarity	NPC274089
0.7254	Intermediate Similarity	NPC255447
0.7252	Intermediate Similarity	NPC329011
0.7246	Intermediate Similarity	NPC476278
0.7241	Intermediate Similarity	NPC127741
0.7239	Intermediate Similarity	NPC2265
0.72	Intermediate Similarity	NPC138775
0.7197	Intermediate Similarity	NPC273814
0.7185	Intermediate Similarity	NPC470545
0.7181	Intermediate Similarity	NPC209509
0.7163	Intermediate Similarity	NPC89923
0.7163	Intermediate Similarity	NPC105114
0.7163	Intermediate Similarity	NPC239990
0.7163	Intermediate Similarity	NPC152850
0.7163	Intermediate Similarity	NPC71933
0.7153	Intermediate Similarity	NPC476183
0.7152	Intermediate Similarity	NPC476750
0.7143	Intermediate Similarity	NPC153007
0.7132	Intermediate Similarity	NPC470546
0.7115	Intermediate Similarity	NPC93343
0.7113	Intermediate Similarity	NPC111428
0.7111	Intermediate Similarity	NPC470544
0.7101	Intermediate Similarity	NPC476281
0.7101	Intermediate Similarity	NPC476184
0.7097	Intermediate Similarity	NPC25565
0.7095	Intermediate Similarity	NPC263493
0.7095	Intermediate Similarity	NPC269398
0.7092	Intermediate Similarity	NPC136453
0.7083	Intermediate Similarity	NPC326966
0.7078	Intermediate Similarity	NPC472761
0.7071	Intermediate Similarity	NPC473938
0.7063	Intermediate Similarity	NPC325651
0.704	Intermediate Similarity	NPC475439
0.704	Intermediate Similarity	NPC473501
0.704	Intermediate Similarity	NPC311242
0.7037	Intermediate Similarity	NPC188010
0.7032	Intermediate Similarity	NPC275839
0.7014	Intermediate Similarity	NPC183722
0.7014	Intermediate Similarity	NPC157311
0.7007	Intermediate Similarity	NPC6570
0.7006	Intermediate Similarity	NPC56635
0.7	Intermediate Similarity	NPC94751
0.7	Intermediate Similarity	NPC142326
0.7	Intermediate Similarity	NPC476978
0.6977	Remote Similarity	NPC194390
0.6977	Remote Similarity	NPC224610
0.6977	Remote Similarity	NPC88267
0.6977	Remote Similarity	NPC113326
0.6974	Remote Similarity	NPC225648
0.6974	Remote Similarity	NPC329761
0.6974	Remote Similarity	NPC475578
0.6968	Remote Similarity	NPC122590
0.6966	Remote Similarity	NPC8761
0.6966	Remote Similarity	NPC45191
0.6966	Remote Similarity	NPC44805
0.6963	Remote Similarity	NPC33742
0.6954	Remote Similarity	NPC5620
0.695	Remote Similarity	NPC476241
0.695	Remote Similarity	NPC476260
0.6933	Remote Similarity	NPC91953
0.6933	Remote Similarity	NPC139326
0.6933	Remote Similarity	NPC476749
0.6929	Remote Similarity	NPC213126
0.6929	Remote Similarity	NPC291027
0.6929	Remote Similarity	NPC84281
0.6929	Remote Similarity	NPC317474
0.6929	Remote Similarity	NPC142577
0.6929	Remote Similarity	NPC7435
0.6929	Remote Similarity	NPC169485
0.6928	Remote Similarity	NPC105717
0.6923	Remote Similarity	NPC476353
0.6918	Remote Similarity	NPC313663
0.6908	Remote Similarity	NPC262077
0.6908	Remote Similarity	NPC314114
0.6901	Remote Similarity	NPC476125
0.6901	Remote Similarity	NPC476179
0.6899	Remote Similarity	NPC471317
0.6892	Remote Similarity	NPC471264
0.6892	Remote Similarity	NPC471265
0.6892	Remote Similarity	NPC478140
0.6889	Remote Similarity	NPC35850
0.6889	Remote Similarity	NPC276949
0.688	Remote Similarity	NPC58674
0.688	Remote Similarity	NPC303045
0.688	Remote Similarity	NPC161972
0.6879	Remote Similarity	NPC6975
0.6875	Remote Similarity	NPC116057
0.6875	Remote Similarity	NPC472413
0.6871	Remote Similarity	NPC64897
0.6871	Remote Similarity	NPC90693
0.6871	Remote Similarity	NPC132847
0.6867	Remote Similarity	NPC197921
0.6867	Remote Similarity	NPC239770
0.6863	Remote Similarity	NPC328824
0.6863	Remote Similarity	NPC145113
0.6857	Remote Similarity	NPC71684
0.6849	Remote Similarity	NPC246079
0.6846	Remote Similarity	NPC98424
0.6846	Remote Similarity	NPC132636
0.6846	Remote Similarity	NPC470884
0.6846	Remote Similarity	NPC92784
0.6846	Remote Similarity	NPC178662
0.6846	Remote Similarity	NPC476133
0.6835	Remote Similarity	NPC319950
0.6829	Remote Similarity	NPC258627
0.6829	Remote Similarity	NPC172128
0.6828	Remote Similarity	NPC69496
0.6825	Remote Similarity	NPC261947
0.6824	Remote Similarity	NPC314835
0.6809	Remote Similarity	NPC474862
0.6809	Remote Similarity	NPC109151
0.6803	Remote Similarity	NPC233910
0.6803	Remote Similarity	NPC470392
0.6803	Remote Similarity	NPC245836
0.68	Remote Similarity	NPC239762
0.68	Remote Similarity	NPC163392
0.6795	Remote Similarity	NPC162104
0.6794	Remote Similarity	NPC211551
0.6788	Remote Similarity	NPC9274
0.6786	Remote Similarity	NPC200964
0.6783	Remote Similarity	NPC101719
0.6783	Remote Similarity	NPC472414
0.6779	Remote Similarity	NPC208725
0.6779	Remote Similarity	NPC68865
0.6774	Remote Similarity	NPC245259
0.6774	Remote Similarity	NPC2501
0.6774	Remote Similarity	NPC129666
0.6774	Remote Similarity	NPC476757
0.6772	Remote Similarity	NPC122493
0.6772	Remote Similarity	NPC10781
0.6772	Remote Similarity	NPC293628
0.6772	Remote Similarity	NPC324569
0.677	Remote Similarity	NPC73644
0.6761	Remote Similarity	NPC472415
0.6753	Remote Similarity	NPC135121
0.6752	Remote Similarity	NPC286551
0.6746	Remote Similarity	NPC172925
0.6744	Remote Similarity	NPC128248
0.6744	Remote Similarity	NPC469457
0.6744	Remote Similarity	NPC264728
0.6744	Remote Similarity	NPC136810
0.6744	Remote Similarity	NPC133809
0.6738	Remote Similarity	NPC202521
0.6735	Remote Similarity	NPC42423
0.6719	Remote Similarity	NPC322598
0.6713	Remote Similarity	NPC222466
0.6712	Remote Similarity	NPC200589
0.6711	Remote Similarity	NPC469360
0.6708	Remote Similarity	NPC235460
0.6707	Remote Similarity	NPC317725
0.6707	Remote Similarity	NPC326407
0.6692	Remote Similarity	NPC21929
0.6692	Remote Similarity	NPC318154
0.6691	Remote Similarity	NPC45794
0.669	Remote Similarity	NPC27581
0.6689	Remote Similarity	NPC46098
0.6689	Remote Similarity	NPC268841
0.6689	Remote Similarity	NPC307357
0.6688	Remote Similarity	NPC262216
0.6688	Remote Similarity	NPC49565
0.6688	Remote Similarity	NPC233702
0.6687	Remote Similarity	NPC217801
0.6667	Remote Similarity	NPC474847
0.6667	Remote Similarity	NPC476990
0.6667	Remote Similarity	NPC67043
0.6667	Remote Similarity	NPC471186
0.6667	Remote Similarity	NPC221825
0.6667	Remote Similarity	NPC6913

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 NPC246913 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	97
0.1-0.2	421
0.2-0.3	780
0.3-0.4	1705
0.4-0.5	3464
0.5-0.6	2118
0.6-0.7	517
0.7-0.8	41
0.8-0.85	5
0.85-0.9	2
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8943	High Similarity	NPD4479	Discontinued
0.8661	High Similarity	NPD5618	Discontinued
0.8145	Intermediate Similarity	NPD3644	Approved
0.8145	Intermediate Similarity	NPD3642	Approved
0.8145	Intermediate Similarity	NPD3643	Approved
0.803	Intermediate Similarity	NPD5108	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD5981	Approved
0.7754	Intermediate Similarity	NPD4738	Phase 2
0.7612	Intermediate Similarity	NPD2956	Clinical (unspecified phase)
0.7557	Intermediate Similarity	NPD1348	Approved
0.7552	Intermediate Similarity	NPD6852	Discontinued
0.7551	Intermediate Similarity	NPD8323	Discontinued
0.7465	Intermediate Similarity	NPD6623	Phase 3
0.7463	Intermediate Similarity	NPD4209	Clinical (unspecified phase)
0.7388	Intermediate Similarity	NPD2217	Approved
0.7388	Intermediate Similarity	NPD2218	Phase 2
0.7379	Intermediate Similarity	NPD6865	Phase 2
0.7379	Intermediate Similarity	NPD6864	Phase 2
0.7375	Intermediate Similarity	NPD7997	Clinical (unspecified phase)
0.7353	Intermediate Similarity	NPD3881	Discontinued
0.7333	Intermediate Similarity	NPD4504	Clinical (unspecified phase)
0.7246	Intermediate Similarity	NPD2584	Suspended
0.7246	Intermediate Similarity	NPD3880	Clinical (unspecified phase)
0.7244	Intermediate Similarity	NPD4335	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD8265	Approved
0.7188	Intermediate Similarity	NPD1040	Phase 2
0.7185	Intermediate Similarity	NPD6065	Approved
0.7181	Intermediate Similarity	NPD6860	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD2650	Approved
0.7143	Intermediate Similarity	NPD2652	Approved
0.7143	Intermediate Similarity	NPD4760	Clinical (unspecified phase)
0.7114	Intermediate Similarity	NPD7596	Clinical (unspecified phase)
0.7113	Intermediate Similarity	NPD7828	Discontinued
0.7111	Intermediate Similarity	NPD4574	Approved
0.7111	Intermediate Similarity	NPD4576	Approved
0.7095	Intermediate Similarity	NPD6897	Clinical (unspecified phase)
0.7092	Intermediate Similarity	NPD6302	Clinical (unspecified phase)
0.7086	Intermediate Similarity	NPD7602	Clinical (unspecified phase)
0.7086	Intermediate Similarity	NPD7740	Clinical (unspecified phase)
0.7077	Intermediate Similarity	NPD6038	Clinical (unspecified phase)
0.7075	Intermediate Similarity	NPD6294	Approved
0.7075	Intermediate Similarity	NPD6295	Approved
0.7055	Intermediate Similarity	NPD8643	Discontinued
0.7047	Intermediate Similarity	NPD7720	Phase 2
0.7037	Intermediate Similarity	NPD4031	Approved
0.7037	Intermediate Similarity	NPD4032	Approved
0.7034	Intermediate Similarity	NPD8118	Discontinued
0.7007	Intermediate Similarity	NPD2617	Discontinued
0.7	Intermediate Similarity	NPD6624	Discontinued
0.6963	Remote Similarity	NPD4766	Approved
0.6959	Remote Similarity	NPD8154	Clinical (unspecified phase)
0.6944	Remote Similarity	NPD5202	Clinical (unspecified phase)
0.694	Remote Similarity	NPD2607	Approved
0.6934	Remote Similarity	NPD7522	Discontinued
0.6929	Remote Similarity	NPD2608	Approved
0.6929	Remote Similarity	NPD3132	Approved
0.6929	Remote Similarity	NPD4215	Approved
0.6929	Remote Similarity	NPD2610	Approved
0.6929	Remote Similarity	NPD2609	Approved
0.6929	Remote Similarity	NPD2611	Approved
0.6929	Remote Similarity	NPD3603	Phase 3
0.6929	Remote Similarity	NPD4480	Approved
0.6929	Remote Similarity	NPD4218	Approved
0.6929	Remote Similarity	NPD3131	Approved
0.6929	Remote Similarity	NPD4217	Approved
0.6929	Remote Similarity	NPD7437	Approved
0.6929	Remote Similarity	NPD7436	Approved
0.6929	Remote Similarity	NPD4216	Approved
0.6929	Remote Similarity	NPD2612	Approved
0.6918	Remote Similarity	NPD7715	Approved
0.6918	Remote Similarity	NPD7714	Approved
0.6903	Remote Similarity	NPD6390	Discontinued
0.6897	Remote Similarity	NPD3136	Phase 2
0.6892	Remote Similarity	NPD8172	Phase 2
0.6892	Remote Similarity	NPD8173	Phase 2
0.6884	Remote Similarity	NPD6093	Discontinued
0.6871	Remote Similarity	NPD8416	Discontinued
0.6867	Remote Similarity	NPD7450	Phase 2
0.6867	Remote Similarity	NPD7512	Approved
0.6867	Remote Similarity	NPD7511	Approved
0.6863	Remote Similarity	NPD6552	Clinical (unspecified phase)
0.6861	Remote Similarity	NPD5162	Approved
0.6855	Remote Similarity	NPD7011	Discontinued
0.6855	Remote Similarity	NPD8019	Approved
0.6853	Remote Similarity	NPD6563	Approved
0.6853	Remote Similarity	NPD6564	Approved
0.6853	Remote Similarity	NPD6565	Approved
0.6849	Remote Similarity	NPD4619	Approved
0.6849	Remote Similarity	NPD5581	Approved
0.6849	Remote Similarity	NPD4621	Approved
0.6842	Remote Similarity	NPD4233	Approved
0.6842	Remote Similarity	NPD3646	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD4234	Approved
0.6835	Remote Similarity	NPD6994	Approved
0.6835	Remote Similarity	NPD8417	Discontinued
0.6835	Remote Similarity	NPD6993	Approved
0.6828	Remote Similarity	NPD4125	Approved
0.6828	Remote Similarity	NPD2613	Approved
0.6828	Remote Similarity	NPD6359	Clinical (unspecified phase)
0.6825	Remote Similarity	NPD2895	Discontinued
0.6815	Remote Similarity	NPD8315	Phase 1
0.6809	Remote Similarity	NPD4806	Approved
0.6809	Remote Similarity	NPD4807	Approved
0.6803	Remote Similarity	NPD3088	Approved
0.6803	Remote Similarity	NPD3614	Approved
0.6803	Remote Similarity	NPD3090	Approved
0.6803	Remote Similarity	NPD2573	Approved
0.6803	Remote Similarity	NPD3615	Approved
0.6803	Remote Similarity	NPD4746	Phase 3
0.6803	Remote Similarity	NPD2572	Clinical (unspecified phase)
0.6803	Remote Similarity	NPD2566	Approved
0.6803	Remote Similarity	NPD3089	Approved
0.6803	Remote Similarity	NPD3616	Approved
0.6803	Remote Similarity	NPD2574	Discontinued
0.6803	Remote Similarity	NPD3087	Approved
0.6803	Remote Similarity	NPD4745	Approved
0.6803	Remote Similarity	NPD5729	Clinical (unspecified phase)
0.6803	Remote Similarity	NPD2570	Approved
0.6803	Remote Similarity	NPD2571	Approved
0.6797	Remote Similarity	NPD7253	Phase 3
0.6797	Remote Similarity	NPD3400	Discontinued
0.6795	Remote Similarity	NPD7613	Discontinued
0.6794	Remote Similarity	NPD999	Phase 2
0.6788	Remote Similarity	NPD7508	Discontinued
0.6779	Remote Similarity	NPD6073	Approved
0.6774	Remote Similarity	NPD8165	Discontinued
0.6772	Remote Similarity	NPD9566	Approved
0.6772	Remote Similarity	NPD2487	Clinical (unspecified phase)
0.6765	Remote Similarity	NPD1374	Approved
0.6765	Remote Similarity	NPD1371	Approved
0.6765	Remote Similarity	NPD1373	Approved
0.6765	Remote Similarity	NPD1370	Approved
0.6757	Remote Similarity	NPD6346	Approved
0.6746	Remote Similarity	NPD4814	Discontinued
0.6746	Remote Similarity	NPD688	Clinical (unspecified phase)
0.6742	Remote Similarity	NPD5705	Approved
0.6742	Remote Similarity	NPD5704	Approved
0.6742	Remote Similarity	NPD5706	Approved
0.6739	Remote Similarity	NPD1841	Clinical (unspecified phase)
0.6738	Remote Similarity	NPD4106	Approved
0.6738	Remote Similarity	NPD4135	Approved
0.6738	Remote Similarity	NPD4136	Approved
0.6735	Remote Similarity	NPD8011	Discontinued
0.6713	Remote Similarity	NPD4677	Discontinued
0.6712	Remote Similarity	NPD5201	Approved
0.6712	Remote Similarity	NPD4617	Approved
0.6712	Remote Similarity	NPD5203	Approved
0.6712	Remote Similarity	NPD4620	Approved
0.6711	Remote Similarity	NPD4684	Phase 3
0.6711	Remote Similarity	NPD4152	Approved
0.6711	Remote Similarity	NPD4685	Phase 3
0.6711	Remote Similarity	NPD4686	Approved
0.6708	Remote Similarity	NPD7599	Phase 2
0.6707	Remote Similarity	NPD6746	Phase 2
0.6693	Remote Similarity	NPD1989	Approved
0.6691	Remote Similarity	NPD1837	Clinical (unspecified phase)
0.6691	Remote Similarity	NPD6360	Discontinued
0.669	Remote Similarity	NPD3608	Clinical (unspecified phase)
0.6687	Remote Similarity	NPD7749	Clinical (unspecified phase)
0.6687	Remote Similarity	NPD7105	Phase 1
0.6667	Remote Similarity	NPD6681	Discovery
0.6667	Remote Similarity	NPD7600	Phase 2
0.6667	Remote Similarity	NPD6919	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6325	Discontinued
0.6667	Remote Similarity	NPD5578	Approved
0.6667	Remote Similarity	NPD5725	Approved
0.6667	Remote Similarity	NPD5577	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD5717	Approved
0.6667	Remote Similarity	NPD7510	Approved
0.6667	Remote Similarity	NPD1018	Approved
0.6645	Remote Similarity	NPD4172	Approved
0.6645	Remote Similarity	NPD4173	Approved
0.6644	Remote Similarity	NPD5121	Approved
0.6644	Remote Similarity	NPD5120	Approved
0.6644	Remote Similarity	NPD7084	Phase 3
0.6644	Remote Similarity	NPD4175	Approved
0.6644	Remote Similarity	NPD5204	Approved
0.6644	Remote Similarity	NPD5119	Approved
0.6644	Remote Similarity	NPD3626	Phase 3
0.6644	Remote Similarity	NPD5323	Approved
0.6644	Remote Similarity	NPD5759	Approved
0.6644	Remote Similarity	NPD4177	Approved
0.6642	Remote Similarity	NPD3598	Phase 3
0.6627	Remote Similarity	NPD7795	Phase 2
0.6626	Remote Similarity	NPD8351	Phase 2
0.6623	Remote Similarity	NPD8147	Approved
0.6623	Remote Similarity	NPD8148	Approved
0.6622	Remote Similarity	NPD5299	Approved
0.6619	Remote Similarity	NPD6775	Clinical (unspecified phase)
0.6619	Remote Similarity	NPD3123	Discovery
0.66	Remote Similarity	NPD7113	Clinical (unspecified phase)
0.6597	Remote Similarity	NPD182	Clinical (unspecified phase)
0.6596	Remote Similarity	NPD4105	Approved
0.6596	Remote Similarity	NPD4102	Approved
0.6593	Remote Similarity	NPD1752	Approved
0.6593	Remote Similarity	NPD1756	Approved
0.6589	Remote Similarity	NPD253	Approved
0.6587	Remote Similarity	NPD6690	Approved
0.6581	Remote Similarity	NPD7488	Clinical (unspecified phase)
0.6579	Remote Similarity	NPD6866	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