NPASS Compound

Structure

NPC208293 OpenBabel07101718272D 39 42 0 0 1 0 0 0 0 0999 V2000 1.0057 -7.2404 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9824 -5.5486 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2091 -3.0110 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3677 1.7558 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6598 0.3563 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0289 -3.8569 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5173 -6.3945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5580 -1.0575 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8662 -1.0575 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5580 -0.0808 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8662 -0.0808 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5173 -4.7028 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3632 -1.5459 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0057 -3.8569 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5173 -1.0575 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0204 -1.5459 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1745 -3.0110 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0057 -5.5486 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3632 -2.5226 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.3231 1.5527 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9616 -0.5726 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7121 -1.5459 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7121 0.4076 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0204 -2.5226 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.1745 -1.0575 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3286 -2.5226 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.7121 -2.5226 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9714 -0.1021 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.3973 -0.8923 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.5173 -3.0110 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.3286 -1.5459 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.9767 2.2786 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.9170 -0.7757 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.7121 1.3844 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.5580 -3.0110 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.6250 0.6238 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.3081 -1.2985 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.8662 -3.0110 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 7 2 0 0 0 0 2 18 1 0 0 0 0 3 19 1 0 0 0 0 4 20 1 0 0 0 0 5 21 1 0 0 0 0 7 18 1 0 0 0 0 8 10 1 0 0 0 0 8 22 2 0 0 0 0 9 11 2 0 0 0 0 9 22 1 0 0 0 0 10 23 2 0 0 0 0 11 23 1 0 0 0 0 12 14 1 0 0 0 0 12 18 2 0 0 0 0 13 15 1 0 0 0 0 13 19 1 0 0 0 0 14 30 1 0 0 0 0 16 24 1 0 0 0 0 16 25 2 0 0 0 0 17 24 1 0 0 0 0 17 26 1 0 0 0 0 19 30 1 1 0 0 0 20 32 2 0 0 0 0 20 36 1 0 0 0 0 21 33 2 0 0 0 0 21 37 1 0 0 0 0 22 27 1 0 0 0 0 23 34 1 0 0 0 0 24 38 1 1 0 0 0 25 28 1 0 0 0 0 25 31 1 0 0 0 0 26 30 1 6 0 0 0 26 31 1 0 0 0 0 27 35 2 0 0 0 0 27 38 1 0 0 0 0 28 36 1 1 0 0 0 28 39 1 0 0 0 0 29 31 1 1 0 0 0 29 37 1 0 0 0 0 29 39 1 0 0 0 0 30 6 1 6 0 0 0 31 15 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	536.35
Volume:	563.37
LogP:	5.238
LogD:	4.587
LogS:	-3.774
# Rotatable Bonds:	22
TPSA:	139.05
# H-Bond Aceptor:	9
# H-Bond Donor:	3
# Rings:	2
# Heavy Atoms:	9

MedChem Properties

QED Drug-Likeness Score:	0.136
Synthetic Accessibility Score:	4.346
Fsp3:	0.759
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.834
MDCK Permeability:	3.638725684140809e-05
Pgp-inhibitor:	0.368
Pgp-substrate:	0.844
Human Intestinal Absorption (HIA):	0.031
20% Bioavailability (F20%):	0.964
30% Bioavailability (F30%):	0.985

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.042
Plasma Protein Binding (PPB):	95.668701171875%
Volume Distribution (VD):	5.197
Pgp-substrate:	1.9613219499588013%

ADMET: Metabolism

CYP1A2-inhibitor:	0.089
CYP1A2-substrate:	0.145
CYP2C19-inhibitor:	0.771
CYP2C19-substrate:	0.065
CYP2C9-inhibitor:	0.948
CYP2C9-substrate:	0.942
CYP2D6-inhibitor:	0.191
CYP2D6-substrate:	0.017
CYP3A4-inhibitor:	0.961
CYP3A4-substrate:	0.366

ADMET: Excretion

Clearance (CL):	8.621
Half-life (T1/2):	0.635

ADMET: Toxicity

hERG Blockers:	0.068
Human Hepatotoxicity (H-HT):	0.411
Drug-inuced Liver Injury (DILI):	0.941
AMES Toxicity:	0.022
Rat Oral Acute Toxicity:	0.834
Maximum Recommended Daily Dose:	0.631
Skin Sensitization:	0.362
Carcinogencity:	0.212
Eye Corrosion:	0.003
Eye Irritation:	0.01
Respiratory Toxicity:	0.972

Download Data

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

Natural Product: NPC208293

Natural Product ID:	NPC208293
*Common Name:**	Casearborin A
IUPAC Name:	[(1S,3R,5R,6aS,7R,8R,10aS)-1,3-diacetyloxy-7,8-dimethyl-7-[(2E)-3-methylpenta-2,4-dienyl]-1,3,5,6,6a,8,9,10-octahydrobenzo[d][2]benzofuran-5-yl] 4-hydroxybenzoate
Synonyms:
Standard InCHIKey:	RKOVIXOSRVSKPI-OLAUXWBOSA-N
Standard InCHI:	InChI=1S/C31H38O8/c1-7-18(2)12-14-30(6)19(3)13-15-31-25(28(36-20(4)32)39-29(31)37-21(5)33)16-24(17-26(30)31)38-27(35)22-8-10-23(34)11-9-22/h7-12,16,19,24,26,28-29,34H,1,13-15,17H2,2-6H3/b18-12+/t19-,24+,26+,28+,29-,30-,31-/m1/s1
SMILES:	C=C/C(=C/C[C@]1(C)[C@H](C)CC[C@@]23[C@H]1C[C@@H](OC(=O)c1ccc(cc1)O)C=C3[C@H](O[C@H]2OC(=O)C)OC(=O)C)/C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL501177
PubChem CID:	5352094
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001551] Diterpenoids [CHEMONTID:0001757] Colensane and clerodane diterpenoids

*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
NPO28776	Casearia arborea	Species	Salicaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10843580]
NPO28776	Casearia arborea	Species	Salicaceae	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
Cell Line	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT390	Cell Line	LOX IMVI	Homo sapiens	IC50	=	290.0	nM	PMID[568334]
NPT374	Cell Line	SF-539	Homo sapiens	IC50	=	290.0	nM	PMID[568334]

☑ 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 NPC208293 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	304
0.1-0.2	1203
0.2-0.3	2349
0.3-0.4	4574
0.4-0.5	9529
0.5-0.6	9822
0.6-0.7	9930
0.7-0.8	4834
0.8-0.85	126
0.85-0.9	18
0.9-0.95	1
0.95-1	7

Similarity Score	Similarity Level	Natural Product ID
0.9718	High Similarity	NPC267469
0.9718	High Similarity	NPC87630
0.9718	High Similarity	NPC35160
0.9718	High Similarity	NPC162569
0.9718	High Similarity	NPC116292
0.9718	High Similarity	NPC179128
0.8961	High Similarity	NPC100420
0.8831	High Similarity	NPC477627
0.8776	High Similarity	NPC320734
0.8759	High Similarity	NPC477595
0.8726	High Similarity	NPC469459
0.8726	High Similarity	NPC469396
0.8726	High Similarity	NPC469419
0.8726	High Similarity	NPC469458
0.8726	High Similarity	NPC88176
0.8726	High Similarity	NPC149002
0.871	High Similarity	NPC293568
0.871	High Similarity	NPC117943
0.8699	High Similarity	NPC478250
0.8667	High Similarity	NPC327962
0.8662	High Similarity	NPC473216
0.8662	High Similarity	NPC473399
0.8658	High Similarity	NPC325032
0.8658	High Similarity	NPC477483
0.8623	High Similarity	NPC204579
0.8618	High Similarity	NPC257847
0.86	High Similarity	NPC279442
0.8591	High Similarity	NPC470330
0.8544	High Similarity	NPC265600
0.8543	High Similarity	NPC247219
0.8509	High Similarity	NPC477617
0.8509	High Similarity	NPC148185
0.8489	Intermediate Similarity	NPC110211
0.8487	Intermediate Similarity	NPC289021
0.8487	Intermediate Similarity	NPC158546
0.8477	Intermediate Similarity	NPC161955
0.8446	Intermediate Similarity	NPC204644
0.844	Intermediate Similarity	NPC117899
0.8435	Intermediate Similarity	NPC172311
0.8417	Intermediate Similarity	NPC137416
0.8414	Intermediate Similarity	NPC471345
0.8408	Intermediate Similarity	NPC130489
0.8408	Intermediate Similarity	NPC208676
0.8403	Intermediate Similarity	NPC194970
0.84	Intermediate Similarity	NPC258856
0.8397	Intermediate Similarity	NPC4747
0.8397	Intermediate Similarity	NPC104275
0.8389	Intermediate Similarity	NPC77922
0.8389	Intermediate Similarity	NPC100242
0.8389	Intermediate Similarity	NPC202391
0.8389	Intermediate Similarity	NPC296659
0.8389	Intermediate Similarity	NPC473281
0.8369	Intermediate Similarity	NPC193203
0.8366	Intermediate Similarity	NPC37642
0.8366	Intermediate Similarity	NPC140133
0.8365	Intermediate Similarity	NPC120012
0.8356	Intermediate Similarity	NPC119542
0.8356	Intermediate Similarity	NPC477592
0.8355	Intermediate Similarity	NPC17600
0.8344	Intermediate Similarity	NPC68619
0.8333	Intermediate Similarity	NPC114116
0.8322	Intermediate Similarity	NPC18798
0.8312	Intermediate Similarity	NPC478235
0.831	Intermediate Similarity	NPC194979
0.8303	Intermediate Similarity	NPC80360
0.8303	Intermediate Similarity	NPC469418
0.8303	Intermediate Similarity	NPC260300
0.8301	Intermediate Similarity	NPC52931
0.8299	Intermediate Similarity	NPC477593
0.8293	Intermediate Similarity	NPC469438
0.8289	Intermediate Similarity	NPC66991
0.8286	Intermediate Similarity	NPC49938
0.8282	Intermediate Similarity	NPC13989
0.8278	Intermediate Similarity	NPC97188
0.8278	Intermediate Similarity	NPC75295
0.8276	Intermediate Similarity	NPC477594
0.8269	Intermediate Similarity	NPC472807
0.8269	Intermediate Similarity	NPC172920
0.8269	Intermediate Similarity	NPC156624
0.8258	Intermediate Similarity	NPC229354
0.8253	Intermediate Similarity	NPC195114
0.825	Intermediate Similarity	NPC161151
0.8247	Intermediate Similarity	NPC474620
0.8239	Intermediate Similarity	NPC473744
0.8239	Intermediate Similarity	NPC229894
0.8235	Intermediate Similarity	NPC96599
0.8235	Intermediate Similarity	NPC478236
0.8235	Intermediate Similarity	NPC473719
0.8235	Intermediate Similarity	NPC478234
0.8232	Intermediate Similarity	NPC195972
0.8231	Intermediate Similarity	NPC170718
0.8224	Intermediate Similarity	NPC286038
0.8224	Intermediate Similarity	NPC473149
0.8219	Intermediate Similarity	NPC477874
0.8219	Intermediate Similarity	NPC477596
0.8219	Intermediate Similarity	NPC173569
0.8219	Intermediate Similarity	NPC472374
0.8219	Intermediate Similarity	NPC472372
0.8214	Intermediate Similarity	NPC474532
0.8212	Intermediate Similarity	NPC210330
0.8204	Intermediate Similarity	NPC188217
0.8194	Intermediate Similarity	NPC48671
0.8194	Intermediate Similarity	NPC11892
0.8194	Intermediate Similarity	NPC475093
0.8188	Intermediate Similarity	NPC469911
0.8187	Intermediate Similarity	NPC145847
0.8182	Intermediate Similarity	NPC469354
0.8182	Intermediate Similarity	NPC240592
0.8182	Intermediate Similarity	NPC117346
0.8182	Intermediate Similarity	NPC35097
0.817	Intermediate Similarity	NPC5568
0.817	Intermediate Similarity	NPC469448
0.817	Intermediate Similarity	NPC120728
0.8165	Intermediate Similarity	NPC187205
0.8165	Intermediate Similarity	NPC226759
0.8163	Intermediate Similarity	NPC249817
0.8158	Intermediate Similarity	NPC473147
0.8158	Intermediate Similarity	NPC143246
0.8158	Intermediate Similarity	NPC473867
0.8158	Intermediate Similarity	NPC474268
0.8158	Intermediate Similarity	NPC119773
0.8158	Intermediate Similarity	NPC475539
0.8158	Intermediate Similarity	NPC291153
0.8156	Intermediate Similarity	NPC470816
0.8156	Intermediate Similarity	NPC100402
0.8156	Intermediate Similarity	NPC9180
0.8153	Intermediate Similarity	NPC472835
0.8151	Intermediate Similarity	NPC477893
0.8146	Intermediate Similarity	NPC194938
0.8146	Intermediate Similarity	NPC271451
0.8138	Intermediate Similarity	NPC477407
0.8138	Intermediate Similarity	NPC302844
0.8137	Intermediate Similarity	NPC109990
0.8133	Intermediate Similarity	NPC469397
0.8129	Intermediate Similarity	NPC469477
0.8129	Intermediate Similarity	NPC133430
0.8125	Intermediate Similarity	NPC266365
0.8113	Intermediate Similarity	NPC314795
0.8112	Intermediate Similarity	NPC2596
0.8108	Intermediate Similarity	NPC216940
0.8108	Intermediate Similarity	NPC198621
0.8108	Intermediate Similarity	NPC22676
0.8108	Intermediate Similarity	NPC475482
0.8105	Intermediate Similarity	NPC469498
0.8101	Intermediate Similarity	NPC283480
0.8101	Intermediate Similarity	NPC148323
0.8092	Intermediate Similarity	NPC469513
0.8092	Intermediate Similarity	NPC471305
0.8092	Intermediate Similarity	NPC475528
0.8089	Intermediate Similarity	NPC469417
0.8086	Intermediate Similarity	NPC474301
0.8085	Intermediate Similarity	NPC184219
0.8082	Intermediate Similarity	NPC48929
0.8077	Intermediate Similarity	NPC194705
0.8077	Intermediate Similarity	NPC267091
0.8075	Intermediate Similarity	NPC187934
0.8075	Intermediate Similarity	NPC97637
0.8069	Intermediate Similarity	NPC473777
0.8065	Intermediate Similarity	NPC104172
0.8065	Intermediate Similarity	NPC182350
0.8065	Intermediate Similarity	NPC88886
0.8065	Intermediate Similarity	NPC142654
0.8065	Intermediate Similarity	NPC212257
0.8056	Intermediate Similarity	NPC214246
0.8056	Intermediate Similarity	NPC147561
0.8054	Intermediate Similarity	NPC472547
0.8054	Intermediate Similarity	NPC234548
0.8054	Intermediate Similarity	NPC90614
0.8054	Intermediate Similarity	NPC171207
0.8054	Intermediate Similarity	NPC248287
0.8054	Intermediate Similarity	NPC475400
0.8054	Intermediate Similarity	NPC97667
0.8042	Intermediate Similarity	NPC230331
0.8039	Intermediate Similarity	NPC212808
0.8038	Intermediate Similarity	NPC41880
0.8038	Intermediate Similarity	NPC469399
0.8038	Intermediate Similarity	NPC174599
0.8038	Intermediate Similarity	NPC159692
0.8038	Intermediate Similarity	NPC192219
0.8038	Intermediate Similarity	NPC82190
0.8028	Intermediate Similarity	NPC470818
0.8028	Intermediate Similarity	NPC275576
0.8027	Intermediate Similarity	NPC477896
0.8027	Intermediate Similarity	NPC169398
0.8026	Intermediate Similarity	NPC63304
0.8026	Intermediate Similarity	NPC476473
0.8025	Intermediate Similarity	NPC91288
0.8025	Intermediate Similarity	NPC471861
0.8024	Intermediate Similarity	NPC475054
0.8014	Intermediate Similarity	NPC470815
0.8014	Intermediate Similarity	NPC165612
0.8014	Intermediate Similarity	NPC174991
0.8013	Intermediate Similarity	NPC243891
0.8013	Intermediate Similarity	NPC475379
0.8013	Intermediate Similarity	NPC472658
0.8013	Intermediate Similarity	NPC477894
0.8013	Intermediate Similarity	NPC140151
0.8013	Intermediate Similarity	NPC472657
0.8012	Intermediate Similarity	NPC316539
0.8	Intermediate Similarity	NPC41481

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 NPC208293 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	246
0.1-0.2	767
0.2-0.3	1391
0.3-0.4	2482
0.4-0.5	2334
0.5-0.6	1399
0.6-0.7	453
0.7-0.8	78
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
0.8133	Intermediate Similarity	NPD4628	Phase 3
0.8125	Intermediate Similarity	NPD3764	Approved
0.8065	Intermediate Similarity	NPD7458	Discontinued
0.7971	Intermediate Similarity	NPD9545	Approved
0.7931	Intermediate Similarity	NPD5952	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD8166	Discontinued
0.7742	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7712	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7703	Intermediate Similarity	NPD6663	Approved
0.7671	Intermediate Similarity	NPD5736	Approved
0.7665	Intermediate Similarity	NPD7799	Discontinued
0.7643	Intermediate Similarity	NPD6273	Approved
0.7616	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7607	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7588	Intermediate Similarity	NPD7685	Pre-registration
0.7582	Intermediate Similarity	NPD7266	Discontinued
0.7578	Intermediate Similarity	NPD37	Approved
0.7564	Intermediate Similarity	NPD7236	Approved
0.7561	Intermediate Similarity	NPD6234	Discontinued
0.7548	Intermediate Similarity	NPD7003	Approved
0.7546	Intermediate Similarity	NPD4965	Approved
0.7546	Intermediate Similarity	NPD4966	Approved
0.7546	Intermediate Similarity	NPD4967	Phase 2
0.7531	Intermediate Similarity	NPD7819	Suspended
0.75	Intermediate Similarity	NPD7075	Discontinued
0.7485	Intermediate Similarity	NPD6559	Discontinued
0.7484	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7471	Intermediate Similarity	NPD8434	Phase 2
0.7468	Intermediate Similarity	NPD2532	Approved
0.7468	Intermediate Similarity	NPD2534	Approved
0.7468	Intermediate Similarity	NPD2533	Approved
0.7456	Intermediate Similarity	NPD3818	Discontinued
0.7456	Intermediate Similarity	NPD7228	Approved
0.7438	Intermediate Similarity	NPD7239	Suspended
0.7436	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7436	Intermediate Similarity	NPD3750	Approved
0.7412	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7401	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7399	Intermediate Similarity	NPD8313	Approved
0.7399	Intermediate Similarity	NPD8312	Approved
0.7386	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7378	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7368	Intermediate Similarity	NPD230	Phase 1
0.7365	Intermediate Similarity	NPD6007	Clinical (unspecified phase)
0.7365	Intermediate Similarity	NPD8127	Discontinued
0.7361	Intermediate Similarity	NPD2932	Approved
0.7358	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7346	Intermediate Similarity	NPD4380	Phase 2
0.7329	Intermediate Similarity	NPD3972	Approved
0.7317	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7317	Intermediate Similarity	NPD8455	Phase 2
0.7308	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7301	Intermediate Similarity	NPD7411	Suspended
0.7294	Intermediate Similarity	NPD7473	Discontinued
0.729	Intermediate Similarity	NPD2935	Discontinued
0.7284	Intermediate Similarity	NPD3226	Approved
0.7278	Intermediate Similarity	NPD6190	Approved
0.7267	Intermediate Similarity	NPD7074	Phase 3
0.725	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7241	Intermediate Similarity	NPD3412	Clinical (unspecified phase)
0.7241	Intermediate Similarity	NPD3019	Approved
0.7239	Intermediate Similarity	NPD7028	Phase 2
0.7239	Intermediate Similarity	NPD6599	Discontinued
0.7229	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7229	Intermediate Similarity	NPD7768	Phase 2
0.7226	Intermediate Similarity	NPD2799	Discontinued
0.7226	Intermediate Similarity	NPD1510	Phase 2
0.7219	Intermediate Similarity	NPD6232	Discontinued
0.7219	Intermediate Similarity	NPD7008	Discontinued
0.7212	Intermediate Similarity	NPD5761	Phase 2
0.7212	Intermediate Similarity	NPD5760	Phase 2
0.7211	Intermediate Similarity	NPD1608	Approved
0.7209	Intermediate Similarity	NPD8470	Clinical (unspecified phase)
0.7209	Intermediate Similarity	NPD7054	Approved
0.7209	Intermediate Similarity	NPD5844	Phase 1
0.7197	Intermediate Similarity	NPD1549	Phase 2
0.7175	Intermediate Similarity	NPD8150	Discontinued
0.7174	Intermediate Similarity	NPD9265	Clinical (unspecified phase)
0.7171	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7168	Intermediate Similarity	NPD7472	Approved
0.7161	Intermediate Similarity	NPD4978	Clinical (unspecified phase)
0.716	Intermediate Similarity	NPD7199	Phase 2
0.7159	Intermediate Similarity	NPD8407	Phase 2
0.7152	Intermediate Similarity	NPD2800	Approved
0.7152	Intermediate Similarity	NPD6801	Discontinued
0.7143	Intermediate Similarity	NPD6355	Discontinued
0.7143	Intermediate Similarity	NPD2181	Clinical (unspecified phase)
0.7135	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7134	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7134	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7134	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7133	Intermediate Similarity	NPD2798	Approved
0.7124	Intermediate Similarity	NPD8032	Phase 2
0.7122	Intermediate Similarity	NPD6831	Clinical (unspecified phase)
0.7115	Intermediate Similarity	NPD3748	Approved
0.7114	Intermediate Similarity	NPD1283	Approved
0.7108	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7107	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7097	Intermediate Similarity	NPD1607	Approved
0.7097	Intermediate Similarity	NPD6651	Approved
0.7086	Intermediate Similarity	NPD6764	Approved
0.7086	Intermediate Similarity	NPD7240	Approved
0.7086	Intermediate Similarity	NPD7251	Discontinued
0.7086	Intermediate Similarity	NPD8368	Discontinued
0.7086	Intermediate Similarity	NPD6765	Approved
0.7083	Intermediate Similarity	NPD3749	Approved
0.7078	Intermediate Similarity	NPD2979	Phase 3
0.7078	Intermediate Similarity	NPD4140	Approved
0.7078	Intermediate Similarity	NPD7966	Clinical (unspecified phase)
0.7078	Intermediate Similarity	NPD1240	Approved
0.7076	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7073	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.707	Intermediate Similarity	NPD5405	Approved
0.707	Intermediate Similarity	NPD5404	Approved
0.707	Intermediate Similarity	NPD6100	Approved
0.707	Intermediate Similarity	NPD5406	Approved
0.707	Intermediate Similarity	NPD6099	Approved
0.707	Intermediate Similarity	NPD5408	Approved
0.707	Intermediate Similarity	NPD2796	Approved
0.7063	Intermediate Similarity	NPD5951	Approved
0.7059	Intermediate Similarity	NPD8320	Phase 1
0.7059	Intermediate Similarity	NPD8319	Approved
0.7059	Intermediate Similarity	NPD6959	Discontinued
0.7055	Intermediate Similarity	NPD4196	Clinical (unspecified phase)
0.7051	Intermediate Similarity	NPD7097	Phase 1
0.7045	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7045	Intermediate Similarity	NPD7808	Phase 3
0.7037	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7029	Intermediate Similarity	NPD6797	Phase 2
0.7025	Intermediate Similarity	NPD6005	Phase 3
0.7025	Intermediate Similarity	NPD6004	Phase 3
0.7025	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.7025	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.7025	Intermediate Similarity	NPD2346	Discontinued
0.7025	Intermediate Similarity	NPD6002	Phase 3
0.7025	Intermediate Similarity	NPD2344	Approved
0.7024	Intermediate Similarity	NPD7058	Phase 2
0.7024	Intermediate Similarity	NPD7057	Phase 3
0.7007	Intermediate Similarity	NPD17	Approved
0.7006	Intermediate Similarity	NPD7033	Discontinued
0.7005	Intermediate Similarity	NPD7435	Discontinued
0.7	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD1876	Approved
0.7	Intermediate Similarity	NPD4110	Phase 3
0.6975	Remote Similarity	NPD6799	Approved
0.6966	Remote Similarity	NPD9493	Approved
0.6962	Remote Similarity	NPD2438	Suspended
0.6962	Remote Similarity	NPD1551	Phase 2
0.6954	Remote Similarity	NPD2797	Approved
0.6954	Remote Similarity	NPD1470	Approved
0.6948	Remote Similarity	NPD3268	Approved
0.6948	Remote Similarity	NPD2313	Discontinued
0.6946	Remote Similarity	NPD1934	Approved
0.694	Remote Similarity	NPD6534	Approved
0.694	Remote Similarity	NPD6535	Approved
0.6931	Remote Similarity	NPD7999	Approved
0.6928	Remote Similarity	NPD6832	Phase 2
0.6927	Remote Similarity	NPD6785	Approved
0.6927	Remote Similarity	NPD6784	Approved
0.6919	Remote Similarity	NPD5710	Approved
0.6919	Remote Similarity	NPD5711	Approved
0.6919	Remote Similarity	NPD7229	Phase 3
0.6919	Remote Similarity	NPD7699	Phase 2
0.6919	Remote Similarity	NPD7700	Phase 2
0.6914	Remote Similarity	NPD7440	Discontinued
0.6913	Remote Similarity	NPD1281	Approved
0.6913	Remote Similarity	NPD1201	Approved
0.6901	Remote Similarity	NPD5494	Approved
0.6899	Remote Similarity	NPD1509	Clinical (unspecified phase)
0.6899	Remote Similarity	NPD4308	Phase 3
0.6892	Remote Similarity	NPD5125	Phase 3
0.6892	Remote Similarity	NPD5126	Approved
0.6892	Remote Similarity	NPD7163	Clinical (unspecified phase)
0.6879	Remote Similarity	NPD2182	Approved
0.6871	Remote Similarity	NPD3091	Approved
0.6871	Remote Similarity	NPD7390	Discontinued
0.6867	Remote Similarity	NPD6591	Clinical (unspecified phase)
0.6864	Remote Similarity	NPD3817	Phase 2
0.6857	Remote Similarity	NPD7177	Discontinued
0.6857	Remote Similarity	NPD7893	Clinical (unspecified phase)
0.6852	Remote Similarity	NPD2309	Approved
0.6848	Remote Similarity	NPD920	Approved
0.6846	Remote Similarity	NPD7457	Clinical (unspecified phase)
0.6846	Remote Similarity	NPD3026	Approved
0.6846	Remote Similarity	NPD3023	Approved
0.6845	Remote Similarity	NPD6777	Approved
0.6845	Remote Similarity	NPD6779	Approved
0.6845	Remote Similarity	NPD6776	Approved
0.6845	Remote Similarity	NPD6780	Approved
0.6845	Remote Similarity	NPD6778	Approved
0.6845	Remote Similarity	NPD6782	Approved
0.6845	Remote Similarity	NPD6781	Approved
0.6842	Remote Similarity	NPD5537	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD3094	Phase 2
0.6842	Remote Similarity	NPD1164	Approved
0.6839	Remote Similarity	NPD3451	Clinical (unspecified phase)
0.6839	Remote Similarity	NPD6798	Discontinued
0.6829	Remote Similarity	NPD7422	Clinical (unspecified phase)
0.6828	Remote Similarity	NPD2629	Approved
0.6825	Remote Similarity	NPD7698	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