NPASS Compound

Structure

NPC113325 OpenBabel07101718272D 31 33 0 0 1 0 0 0 0 0999 V2000 -3.8005 0.4173 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5296 -3.0827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2024 -4.0827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.6665 1.9173 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3119 -3.9746 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3338 -3.7667 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9811 -3.2315 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8005 -1.5827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.6665 -1.0827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0248 -2.8157 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6720 -2.2804 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9345 -1.0827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3849 -1.1215 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.6665 -0.0827 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.3364 -2.5827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2024 -3.0827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.5326 1.4173 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6939 -2.0725 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0685 -1.5827 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.4067 -0.9135 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.3364 -1.5827 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.5326 0.4173 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.0685 -2.5827 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.9945 -0.1045 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2024 -1.0827 0.0000 C 0 0 1 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 -6.3986 1.9173 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.3986 -0.0827 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.9345 -3.0827 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.6637 0.6386 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.1970 -0.9781 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2 15 1 0 0 0 0 3 16 1 0 0 0 0 4 17 1 0 0 0 0 5 6 2 0 0 0 0 5 7 1 0 0 0 0 6 10 1 0 0 0 0 7 11 2 0 0 0 0 8 9 1 0 0 0 0 8 12 2 0 0 0 0 9 14 1 0 0 0 0 10 18 2 0 0 0 0 11 18 1 0 0 0 0 12 19 1 0 0 0 0 13 18 1 0 0 0 0 14 1 1 1 0 0 0 14 22 1 0 0 0 0 15 16 2 0 0 0 0 15 21 1 0 0 0 0 16 23 1 0 0 0 0 17 22 1 0 0 0 0 17 27 2 0 0 0 0 19 23 1 0 0 0 0 19 25 1 6 0 0 0 20 13 1 1 0 0 0 20 21 1 0 0 0 0 20 26 1 0 0 0 0 21 25 1 6 0 0 0 22 28 1 1 0 0 0 23 29 1 1 0 0 0 24 25 1 0 0 0 0 24 26 2 0 0 0 0 24 30 1 0 0 0 0 25 31 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	427.24
Volume:	451.779
LogP:	2.717
LogD:	2.718
LogS:	-3.71
# Rotatable Bonds:	7
TPSA:	106.86
# H-Bond Aceptor:	6
# H-Bond Donor:	4
# Rings:	3
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.498
Synthetic Accessibility Score:	4.791
Fsp3:	0.52
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
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:	-5.185
MDCK Permeability:	6.0166938055772334e-05
Pgp-inhibitor:	0.009
Pgp-substrate:	0.988
Human Intestinal Absorption (HIA):	0.047
20% Bioavailability (F20%):	0.005
30% Bioavailability (F30%):	0.002

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.734
Plasma Protein Binding (PPB):	97.07748413085938%
Volume Distribution (VD):	1.452
Pgp-substrate:	3.7018940448760986%

ADMET: Metabolism

CYP1A2-inhibitor:	0.038
CYP1A2-substrate:	0.122
CYP2C19-inhibitor:	0.098
CYP2C19-substrate:	0.743
CYP2C9-inhibitor:	0.038
CYP2C9-substrate:	0.121
CYP2D6-inhibitor:	0.009
CYP2D6-substrate:	0.45
CYP3A4-inhibitor:	0.144
CYP3A4-substrate:	0.359

ADMET: Excretion

Clearance (CL):	8.967
Half-life (T1/2):	0.093

ADMET: Toxicity

hERG Blockers:	0.025
Human Hepatotoxicity (H-HT):	0.663
Drug-inuced Liver Injury (DILI):	0.337
AMES Toxicity:	0.012
Rat Oral Acute Toxicity:	0.82
Maximum Recommended Daily Dose:	0.568
Skin Sensitization:	0.254
Carcinogencity:	0.124
Eye Corrosion:	0.003
Eye Irritation:	0.01
Respiratory Toxicity:	0.977

Download Data

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

Natural Product: NPC113325

Natural Product ID:	NPC113325
*Common Name:**	Cytochalasin Z15
IUPAC Name:	(3S,3aS,6S,7S,7aS)-3-benzyl-6,7a-dihydroxy-7-[(E,4S,5R)-5-hydroxy-4-methyl-6-oxohept-1-enyl]-4,5-dimethyl-3,3a,6,7-tetrahydro-2H-isoindol-1-one
Synonyms:	Cytochalasin Z15
Standard InCHIKey:	RQWVQCYJRCZFED-LYRHPEFXSA-N
Standard InCHI:	InChI=1S/C25H33NO5/c1-14(22(28)17(4)27)9-8-12-19-23(29)16(3)15(2)21-20(26-24(30)25(19,21)31)13-18-10-6-5-7-11-18/h5-8,10-12,14,19-23,28-29,31H,9,13H2,1-4H3,(H,26,30)/b12-8+/t14-,19-,20-,21-,22+,23+,25+/m0/s1
SMILES:	C[C@@H](C/C=C/[C@H]1[C@@H](C(=C(C)[C@H]2[C@H](Cc3ccccc3)N=C([C@@]12O)O)C)O)[C@H](C(=O)C)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL460271
PubChem CID:	24970445
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0001819] Isoindoles and derivatives [CHEMONTID:0002496] Isoindolines [CHEMONTID:0001820] Isoindolones

*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
NPO33507	spicaria elegans	Species	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[16792402]
NPO33507	spicaria elegans	Species	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[18507474]

☑ 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	4

Activity Type	# Activity
Cell Line	4

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT168	Cell Line	P388	Mus musculus	IC50	>	100000.0	nM	PMID[476027]
NPT81	Cell Line	A549	Homo sapiens	IC50	>	100000.0	nM	PMID[476027]
NPT116	Cell Line	HL-60	Homo sapiens	IC50	>	100000.0	nM	PMID[476027]
NPT181	Cell Line	Bel-7402	Homo sapiens	IC50	>	100000.0	nM	PMID[476027]

☑ 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 NPC113325 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	121
0.1-0.2	652
0.2-0.3	2098
0.3-0.4	8442
0.4-0.5	22586
0.5-0.6	7885
0.6-0.7	818
0.7-0.8	74
0.8-0.85	6
0.85-0.9	8
0.9-0.95	4
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC279045
0.9921	High Similarity	NPC228511
0.9462	High Similarity	NPC175870
0.9365	High Similarity	NPC278097
0.9302	High Similarity	NPC42423
0.9259	High Similarity	NPC49565
0.9219	High Similarity	NPC71271
0.8984	High Similarity	NPC472414
0.8923	High Similarity	NPC295478
0.8828	High Similarity	NPC472415
0.8824	High Similarity	NPC239770
0.8759	High Similarity	NPC111586
0.8759	High Similarity	NPC108852
0.8759	High Similarity	NPC261709
0.8507	High Similarity	NPC183722
0.8472	Intermediate Similarity	NPC4108
0.8467	Intermediate Similarity	NPC208725
0.8456	Intermediate Similarity	NPC64897
0.8456	Intermediate Similarity	NPC90693
0.844	Intermediate Similarity	NPC262216
0.838	Intermediate Similarity	NPC237240
0.838	Intermediate Similarity	NPC31171
0.8222	Intermediate Similarity	NPC472413
0.8207	Intermediate Similarity	NPC201692
0.8088	Intermediate Similarity	NPC116057
0.8069	Intermediate Similarity	NPC173934
0.7806	Intermediate Similarity	NPC15506
0.7799	Intermediate Similarity	NPC477115
0.7727	Intermediate Similarity	NPC156348
0.7519	Intermediate Similarity	NPC188010
0.7431	Intermediate Similarity	NPC477680
0.7246	Intermediate Similarity	NPC190663
0.7234	Intermediate Similarity	NPC477249
0.7234	Intermediate Similarity	NPC477248
0.723	Intermediate Similarity	NPC471201
0.7226	Intermediate Similarity	NPC314992
0.719	Intermediate Similarity	NPC146097
0.719	Intermediate Similarity	NPC339338
0.719	Intermediate Similarity	NPC227905
0.7143	Intermediate Similarity	NPC160493
0.7123	Intermediate Similarity	NPC328070
0.7114	Intermediate Similarity	NPC322526
0.7097	Intermediate Similarity	NPC185404
0.7092	Intermediate Similarity	NPC35996
0.7089	Intermediate Similarity	NPC217801
0.708	Intermediate Similarity	NPC2265
0.7077	Intermediate Similarity	NPC113326
0.7077	Intermediate Similarity	NPC194390
0.7077	Intermediate Similarity	NPC224610
0.7077	Intermediate Similarity	NPC88267
0.7059	Intermediate Similarity	NPC328824
0.7047	Intermediate Similarity	NPC473052
0.7047	Intermediate Similarity	NPC473055
0.7	Intermediate Similarity	NPC478016
0.7	Intermediate Similarity	NPC478015
0.7	Intermediate Similarity	NPC478014
0.7	Intermediate Similarity	NPC80150
0.6993	Remote Similarity	NPC47667
0.6985	Remote Similarity	NPC474544
0.6985	Remote Similarity	NPC1986
0.6978	Remote Similarity	NPC237420
0.6968	Remote Similarity	NPC94602
0.6968	Remote Similarity	NPC476757
0.6948	Remote Similarity	NPC44649
0.6913	Remote Similarity	NPC118099
0.6913	Remote Similarity	NPC79465
0.6913	Remote Similarity	NPC475318
0.6913	Remote Similarity	NPC49577
0.6913	Remote Similarity	NPC476102
0.6913	Remote Similarity	NPC151706
0.6913	Remote Similarity	NPC475598
0.6913	Remote Similarity	NPC474787
0.6913	Remote Similarity	NPC273907
0.6913	Remote Similarity	NPC293377
0.6913	Remote Similarity	NPC260045
0.6913	Remote Similarity	NPC76785
0.6913	Remote Similarity	NPC474811
0.6913	Remote Similarity	NPC90194
0.6913	Remote Similarity	NPC9687
0.6913	Remote Similarity	NPC474855
0.6894	Remote Similarity	NPC235460
0.6882	Remote Similarity	NPC475345
0.6867	Remote Similarity	NPC64205
0.6857	Remote Similarity	NPC310467
0.6846	Remote Similarity	NPC132847
0.6846	Remote Similarity	NPC469457
0.6842	Remote Similarity	NPC191215
0.6842	Remote Similarity	NPC475649
0.6842	Remote Similarity	NPC274089
0.679	Remote Similarity	NPC476194
0.6786	Remote Similarity	NPC278272
0.6786	Remote Similarity	NPC120667
0.6786	Remote Similarity	NPC169328
0.6782	Remote Similarity	NPC295531
0.6779	Remote Similarity	NPC3202
0.6772	Remote Similarity	NPC470274
0.6765	Remote Similarity	NPC476113
0.6765	Remote Similarity	NPC203005
0.6761	Remote Similarity	NPC453583
0.6761	Remote Similarity	NPC475336
0.6761	Remote Similarity	NPC473300
0.6761	Remote Similarity	NPC317882
0.6761	Remote Similarity	NPC471754
0.6757	Remote Similarity	NPC49272
0.6755	Remote Similarity	NPC6570
0.6746	Remote Similarity	NPC211713
0.6746	Remote Similarity	NPC88378
0.6744	Remote Similarity	NPC469973
0.6743	Remote Similarity	NPC327699
0.6736	Remote Similarity	NPC108286
0.6732	Remote Similarity	NPC150712
0.6731	Remote Similarity	NPC260194
0.6731	Remote Similarity	NPC475578
0.6723	Remote Similarity	NPC33372
0.6723	Remote Similarity	NPC67246
0.6719	Remote Similarity	NPC58674
0.6715	Remote Similarity	NPC471189
0.6713	Remote Similarity	NPC476184
0.6713	Remote Similarity	NPC476281
0.6712	Remote Similarity	NPC65310
0.6688	Remote Similarity	NPC91953
0.6687	Remote Similarity	NPC275839
0.6667	Remote Similarity	NPC474862
0.6667	Remote Similarity	NPC473400
0.6667	Remote Similarity	NPC207675
0.6667	Remote Similarity	NPC306001
0.6667	Remote Similarity	NPC324251
0.6667	Remote Similarity	NPC153007
0.6667	Remote Similarity	NPC275170
0.6667	Remote Similarity	NPC471629
0.6667	Remote Similarity	NPC212699
0.6667	Remote Similarity	NPC206211
0.6648	Remote Similarity	NPC471395
0.6646	Remote Similarity	NPC476268
0.6645	Remote Similarity	NPC68865
0.6645	Remote Similarity	NPC475128
0.6643	Remote Similarity	NPC476183
0.6643	Remote Similarity	NPC477061
0.6643	Remote Similarity	NPC45777
0.6642	Remote Similarity	NPC211551
0.6625	Remote Similarity	NPC472761
0.6623	Remote Similarity	NPC197921
0.6621	Remote Similarity	NPC476278
0.6621	Remote Similarity	NPC6975
0.6617	Remote Similarity	NPC471317
0.6611	Remote Similarity	NPC242662
0.6611	Remote Similarity	NPC321072
0.6611	Remote Similarity	NPC215892
0.6611	Remote Similarity	NPC191193
0.6606	Remote Similarity	NPC67080
0.66	Remote Similarity	NPC246913
0.6594	Remote Similarity	NPC111108
0.6582	Remote Similarity	NPC473541
0.6581	Remote Similarity	NPC251439
0.6577	Remote Similarity	NPC478147
0.6575	Remote Similarity	NPC476241
0.6575	Remote Similarity	NPC208553
0.6575	Remote Similarity	NPC181964
0.6575	Remote Similarity	NPC471606
0.6575	Remote Similarity	NPC476260
0.6569	Remote Similarity	NPC113012
0.6569	Remote Similarity	NPC122926
0.6564	Remote Similarity	NPC197743
0.6564	Remote Similarity	NPC297145
0.6564	Remote Similarity	NPC93343
0.6558	Remote Similarity	NPC476259
0.6556	Remote Similarity	NPC80599
0.6556	Remote Similarity	NPC313663
0.6554	Remote Similarity	NPC81135
0.6552	Remote Similarity	NPC213126
0.6552	Remote Similarity	NPC252878
0.6552	Remote Similarity	NPC317474
0.6552	Remote Similarity	NPC84281
0.6552	Remote Similarity	NPC169485
0.6552	Remote Similarity	NPC291027
0.6549	Remote Similarity	NPC471553
0.6547	Remote Similarity	NPC273814
0.6544	Remote Similarity	NPC140251
0.6544	Remote Similarity	NPC472980
0.6544	Remote Similarity	NPC307903
0.6541	Remote Similarity	NPC132771
0.6538	Remote Similarity	NPC25565
0.6538	Remote Similarity	NPC473558
0.6535	Remote Similarity	NPC316108
0.6533	Remote Similarity	NPC262819
0.6531	Remote Similarity	NPC476179
0.6531	Remote Similarity	NPC476125
0.6517	Remote Similarity	NPC471623
0.651	Remote Similarity	NPC40488
0.651	Remote Similarity	NPC197680
0.651	Remote Similarity	NPC259098
0.651	Remote Similarity	NPC296712
0.6507	Remote Similarity	NPC473870
0.6507	Remote Similarity	NPC46427
0.6507	Remote Similarity	NPC473871
0.6497	Remote Similarity	NPC315266
0.6497	Remote Similarity	NPC473922
0.6496	Remote Similarity	NPC475282
0.6494	Remote Similarity	NPC291305
0.6493	Remote Similarity	NPC202613

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 NPC113325 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	107
0.1-0.2	412
0.2-0.3	816
0.3-0.4	2275
0.4-0.5	3562
0.5-0.6	1677
0.6-0.7	293
0.7-0.8	8
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
0.838	Intermediate Similarity	NPD7274	Clinical (unspecified phase)
0.7357	Intermediate Similarity	NPD6325	Discontinued
0.7226	Intermediate Similarity	NPD2217	Approved
0.7226	Intermediate Similarity	NPD2218	Phase 2
0.7045	Intermediate Similarity	NPD6406	Approved
0.6986	Remote Similarity	NPD4738	Phase 2
0.6929	Remote Similarity	NPD5981	Approved
0.6889	Remote Similarity	NPD3644	Approved
0.6889	Remote Similarity	NPD3643	Approved
0.6889	Remote Similarity	NPD3642	Approved
0.6846	Remote Similarity	NPD8265	Approved
0.6821	Remote Similarity	NPD5036	Approved
0.6802	Remote Similarity	NPD5035	Approved
0.6786	Remote Similarity	NPD7522	Discontinued
0.6784	Remote Similarity	NPD5030	Phase 2
0.6782	Remote Similarity	NPD5037	Approved
0.6782	Remote Similarity	NPD5038	Approved
0.6774	Remote Similarity	NPD6676	Phase 2
0.6744	Remote Similarity	NPD5026	Approved
0.6744	Remote Similarity	NPD5034	Approved
0.6744	Remote Similarity	NPD36	Approved
0.6744	Remote Similarity	NPD4955	Approved
0.6744	Remote Similarity	NPD5028	Approved
0.6744	Remote Similarity	NPD4954	Approved
0.6718	Remote Similarity	NPD4760	Clinical (unspecified phase)
0.6714	Remote Similarity	NPD3123	Discovery
0.6712	Remote Similarity	NPD2626	Approved
0.6712	Remote Similarity	NPD2625	Approved
0.6712	Remote Similarity	NPD2628	Approved
0.6712	Remote Similarity	NPD2160	Approved
0.6712	Remote Similarity	NPD2627	Approved
0.6712	Remote Similarity	NPD2159	Approved
0.6667	Remote Similarity	NPD2575	Approved
0.6667	Remote Similarity	NPD5618	Discontinued
0.6647	Remote Similarity	NPD5032	Approved
0.6644	Remote Similarity	NPD3136	Phase 2
0.6642	Remote Similarity	NPD4141	Clinical (unspecified phase)
0.662	Remote Similarity	NPD4479	Discontinued
0.661	Remote Similarity	NPD8360	Approved
0.661	Remote Similarity	NPD8361	Approved
0.6608	Remote Similarity	NPD8470	Clinical (unspecified phase)
0.6605	Remote Similarity	NPD8417	Discontinued
0.66	Remote Similarity	NPD4619	Approved
0.66	Remote Similarity	NPD4621	Approved
0.6591	Remote Similarity	NPD8424	Clinical (unspecified phase)
0.6589	Remote Similarity	NPD4814	Discontinued
0.6575	Remote Similarity	NPD8485	Approved
0.6571	Remote Similarity	NPD8407	Phase 2
0.6561	Remote Similarity	NPD3400	Discontinued
0.6556	Remote Similarity	NPD7715	Approved
0.6556	Remote Similarity	NPD7714	Approved
0.6552	Remote Similarity	NPD4217	Approved
0.6552	Remote Similarity	NPD3131	Approved
0.6552	Remote Similarity	NPD4218	Approved
0.6552	Remote Similarity	NPD4806	Approved
0.6552	Remote Similarity	NPD2609	Approved
0.6552	Remote Similarity	NPD2612	Approved
0.6552	Remote Similarity	NPD4807	Approved
0.6552	Remote Similarity	NPD2608	Approved
0.6552	Remote Similarity	NPD4215	Approved
0.6552	Remote Similarity	NPD3132	Approved
0.6552	Remote Similarity	NPD2610	Approved
0.6552	Remote Similarity	NPD2611	Approved
0.6552	Remote Similarity	NPD4216	Approved
0.6536	Remote Similarity	NPD8173	Phase 2
0.6536	Remote Similarity	NPD8172	Phase 2
0.6528	Remote Similarity	NPD5305	Approved
0.6528	Remote Similarity	NPD5306	Approved
0.6517	Remote Similarity	NPD6836	Approved
0.6517	Remote Similarity	NPD8435	Approved
0.6516	Remote Similarity	NPD6897	Clinical (unspecified phase)
0.6513	Remote Similarity	NPD6310	Approved
0.6513	Remote Similarity	NPD6309	Approved
0.6513	Remote Similarity	NPD6311	Approved
0.651	Remote Similarity	NPD3662	Phase 3
0.651	Remote Similarity	NPD3663	Approved
0.651	Remote Similarity	NPD3664	Approved
0.651	Remote Similarity	NPD5204	Approved
0.651	Remote Similarity	NPD3661	Approved
0.6507	Remote Similarity	NPD5108	Clinical (unspecified phase)
0.6503	Remote Similarity	NPD2227	Clinical (unspecified phase)
0.6494	Remote Similarity	NPD5039	Approved
0.6494	Remote Similarity	NPD5029	Approved
0.6494	Remote Similarity	NPD8368	Discontinued
0.6494	Remote Similarity	NPD5027	Approved
0.6494	Remote Similarity	NPD5031	Approved
0.6493	Remote Similarity	NPD5738	Clinical (unspecified phase)
0.6483	Remote Similarity	NPD2956	Clinical (unspecified phase)
0.6474	Remote Similarity	NPD7978	Discontinued
0.6474	Remote Similarity	NPD4956	Approved
0.6467	Remote Similarity	NPD4620	Approved
0.6467	Remote Similarity	NPD5201	Approved
0.6467	Remote Similarity	NPD5203	Approved
0.6467	Remote Similarity	NPD8486	Clinical (unspecified phase)
0.6467	Remote Similarity	NPD4617	Approved
0.6467	Remote Similarity	NPD5202	Clinical (unspecified phase)
0.6467	Remote Similarity	NPD2613	Approved
0.6463	Remote Similarity	NPD5158	Clinical (unspecified phase)
0.6463	Remote Similarity	NPD5157	Phase 1
0.6463	Remote Similarity	NPD5159	Phase 2
0.646	Remote Similarity	NPD7613	Discontinued
0.6456	Remote Similarity	NPD7488	Clinical (unspecified phase)
0.6454	Remote Similarity	NPD2629	Approved
0.6454	Remote Similarity	NPD1711	Phase 2
0.6447	Remote Similarity	NPD5729	Clinical (unspecified phase)
0.6444	Remote Similarity	NPD179	Clinical (unspecified phase)
0.6418	Remote Similarity	NPD4719	Phase 2
0.6418	Remote Similarity	NPD4818	Approved
0.6418	Remote Similarity	NPD4817	Approved
0.6415	Remote Similarity	NPD8323	Discontinued
0.6414	Remote Similarity	NPD7725	Approved
0.6405	Remote Similarity	NPD5119	Approved
0.6405	Remote Similarity	NPD5120	Approved
0.6405	Remote Similarity	NPD5121	Approved
0.6405	Remote Similarity	NPD2238	Phase 2
0.64	Remote Similarity	NPD3626	Phase 3
0.64	Remote Similarity	NPD7084	Phase 3
0.6397	Remote Similarity	NPD999	Phase 2
0.6386	Remote Similarity	NPD7972	Discontinued
0.637	Remote Similarity	NPD4135	Approved
0.637	Remote Similarity	NPD6647	Phase 2
0.637	Remote Similarity	NPD4136	Approved
0.637	Remote Similarity	NPD4106	Approved
0.6364	Remote Similarity	NPD7113	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD7749	Clinical (unspecified phase)
0.6358	Remote Similarity	NPD7527	Clinical (unspecified phase)
0.6358	Remote Similarity	NPD52	Approved
0.6358	Remote Similarity	NPD7526	Approved
0.6354	Remote Similarity	NPD5968	Phase 3
0.6345	Remote Similarity	NPD1710	Approved
0.634	Remote Similarity	NPD3089	Approved
0.634	Remote Similarity	NPD3614	Approved
0.634	Remote Similarity	NPD3087	Approved
0.634	Remote Similarity	NPD3088	Approved
0.634	Remote Similarity	NPD3616	Approved
0.634	Remote Similarity	NPD2573	Approved
0.634	Remote Similarity	NPD2574	Discontinued
0.634	Remote Similarity	NPD2570	Approved
0.634	Remote Similarity	NPD2572	Clinical (unspecified phase)
0.634	Remote Similarity	NPD4745	Approved
0.634	Remote Similarity	NPD3615	Approved
0.634	Remote Similarity	NPD2566	Approved
0.634	Remote Similarity	NPD4746	Phase 3
0.634	Remote Similarity	NPD2571	Approved
0.634	Remote Similarity	NPD3090	Approved
0.6327	Remote Similarity	NPD3529	Phase 2
0.6327	Remote Similarity	NPD2173	Clinical (unspecified phase)
0.6312	Remote Similarity	NPD7910	Clinical (unspecified phase)
0.6308	Remote Similarity	NPD6690	Approved
0.6306	Remote Similarity	NPD2161	Phase 2
0.6304	Remote Similarity	NPD4095	Clinical (unspecified phase)
0.6301	Remote Similarity	NPD5033	Approved
0.6296	Remote Similarity	NPD854	Approved
0.6296	Remote Similarity	NPD855	Approved
0.6294	Remote Similarity	NPD1348	Approved
0.6286	Remote Similarity	NPD5190	Phase 2
0.6282	Remote Similarity	NPD6852	Discontinued
0.6277	Remote Similarity	NPD1018	Approved
0.6273	Remote Similarity	NPD3300	Phase 2
0.6273	Remote Similarity	NPD7236	Approved
0.6268	Remote Similarity	NPD4869	Clinical (unspecified phase)
0.6268	Remote Similarity	NPD2228	Approved
0.6268	Remote Similarity	NPD2234	Approved
0.6268	Remote Similarity	NPD2229	Approved
0.6258	Remote Similarity	NPD4685	Phase 3
0.6258	Remote Similarity	NPD4686	Approved
0.6258	Remote Similarity	NPD4684	Phase 3
0.625	Remote Similarity	NPD3682	Approved
0.625	Remote Similarity	NPD5765	Approved
0.625	Remote Similarity	NPD3681	Approved
0.625	Remote Similarity	NPD6775	Clinical (unspecified phase)
0.625	Remote Similarity	NPD3683	Approved
0.625	Remote Similarity	NPD3680	Approved
0.6233	Remote Similarity	NPD4102	Approved
0.6233	Remote Similarity	NPD4105	Approved
0.6233	Remote Similarity	NPD4209	Clinical (unspecified phase)
0.6232	Remote Similarity	NPD6685	Approved
0.6229	Remote Similarity	NPD4603	Phase 2
0.6228	Remote Similarity	NPD7011	Discontinued
0.6224	Remote Similarity	NPD9614	Approved
0.6224	Remote Similarity	NPD9618	Approved
0.6221	Remote Similarity	NPD7315	Approved
0.6216	Remote Similarity	NPD7282	Approved
0.6216	Remote Similarity	NPD5350	Clinical (unspecified phase)
0.6216	Remote Similarity	NPD5351	Clinical (unspecified phase)
0.6207	Remote Similarity	NPD1758	Phase 1
0.6203	Remote Similarity	NPD4914	Approved
0.6203	Remote Similarity	NPD4173	Approved
0.6203	Remote Similarity	NPD4172	Approved
0.6203	Remote Similarity	NPD9570	Approved
0.62	Remote Similarity	NPD6330	Clinical (unspecified phase)
0.6197	Remote Similarity	NPD2607	Approved
0.6196	Remote Similarity	NPD8389	Clinical (unspecified phase)
0.6194	Remote Similarity	NPD9612	Approved
0.6194	Remote Similarity	NPD9609	Approved
0.6194	Remote Similarity	NPD8416	Discontinued
0.6194	Remote Similarity	NPD9611	Approved
0.6187	Remote Similarity	NPD6038	Clinical (unspecified phase)
0.6182	Remote Similarity	NPD7239	Suspended
0.6181	Remote Similarity	NPD7508	Discontinued

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