NPASS Compound

Structure

NPC218323 OpenBabel07101719402D 23 24 0 0 0 0 0 0 0 0999 V2000 3.4641 4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9282 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9282 3.0000 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 0.0000 1.0000 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 4.3301 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 2.5000 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 1.7321 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.7942 2.5000 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 4.3301 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 3.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 8.6603 3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 20 1 0 0 0 0 2 23 1 0 0 0 0 3 8 1 0 0 0 0 3 15 2 0 0 0 0 4 9 2 0 0 0 0 4 15 1 0 0 0 0 5 10 1 0 0 0 0 5 16 2 0 0 0 0 6 11 2 0 0 0 0 6 16 1 0 0 0 0 7 12 2 0 0 0 0 7 15 1 0 0 0 0 8 17 2 0 0 0 0 9 17 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 14 1 0 0 0 0 13 16 1 0 0 0 0 14 20 1 0 0 0 0 17 21 1 0 0 0 0 18 23 1 0 0 0 0 19 20 1 0 0 0 0 19 22 2 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	311.15
Volume:	336.343
LogP:	3.05
LogD:	3.325
LogS:	-3.287
# Rotatable Bonds:	7
TPSA:	49.77
# H-Bond Aceptor:	4
# H-Bond Donor:	1
# Rings:	2
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.834
Synthetic Accessibility Score:	1.974
Fsp3:	0.211
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.71
MDCK Permeability:	1.67256839631591e-05
Pgp-inhibitor:	0.794
Pgp-substrate:	0.002
Human Intestinal Absorption (HIA):	0.007
20% Bioavailability (F20%):	0.002
30% Bioavailability (F30%):	0.004

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.273
Plasma Protein Binding (PPB):	96.14435577392578%
Volume Distribution (VD):	0.499
Pgp-substrate:	1.98712158203125%

ADMET: Metabolism

CYP1A2-inhibitor:	0.833
CYP1A2-substrate:	0.954
CYP2C19-inhibitor:	0.836
CYP2C19-substrate:	0.685
CYP2C9-inhibitor:	0.585
CYP2C9-substrate:	0.95
CYP2D6-inhibitor:	0.523
CYP2D6-substrate:	0.924
CYP3A4-inhibitor:	0.519
CYP3A4-substrate:	0.55

ADMET: Excretion

Clearance (CL):	10.17
Half-life (T1/2):	0.865

ADMET: Toxicity

hERG Blockers:	0.873
Human Hepatotoxicity (H-HT):	0.346
Drug-inuced Liver Injury (DILI):	0.047
AMES Toxicity:	0.029
Rat Oral Acute Toxicity:	0.715
Maximum Recommended Daily Dose:	0.413
Skin Sensitization:	0.948
Carcinogencity:	0.57
Eye Corrosion:	0.004
Eye Irritation:	0.226
Respiratory Toxicity:	0.941

Download Data

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

Natural Product: NPC218323

Natural Product ID:	NPC218323
*Common Name:**	Ailanthamide
IUPAC Name:	(E)-3-(4-hydroxyphenyl)-N-[2-(4-methoxyphenyl)ethyl]-N-methylprop-2-enamide
Synonyms:	Ailanthamide
Standard InCHIKey:	FELKBIBTBNGNOU-KPKJPENVSA-N
Standard InCHI:	InChI=1S/C19H21NO3/c1-20(14-13-16-5-10-18(23-2)11-6-16)19(22)12-7-15-3-8-17(21)9-4-15/h3-12,21H,13-14H2,1-2H3/b12-7+
SMILES:	COc1ccc(cc1)CCN(C(=O)/C=C/c1ccc(cc1)O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL556469
PubChem CID:	25195168
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000476] Cinnamic acids and derivatives [CHEMONTID:0001391] Hydroxycinnamic acids and derivatives [CHEMONTID:0000059] Coumaric acids and derivatives

*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
NPO23557	Zanthoxylum ailanthoides	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19128011]
NPO23557	Zanthoxylum ailanthoides	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO23557	Zanthoxylum ailanthoides	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO23557	Zanthoxylum ailanthoides	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	NP ID	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
IC50	2

Activity Type	# Activity
NON-MOLECULAR	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	3.71	ug.mL-1	PMID[572962]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	4.23	ug.mL-1	PMID[572962]

☑ 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 NPC218323 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	163
0.1-0.2	2039
0.2-0.3	7467
0.3-0.4	9854
0.4-0.5	5568
0.5-0.6	12038
0.6-0.7	5108
0.7-0.8	452
0.8-0.85	4
0.85-0.9	3
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.8769	High Similarity	NPC266425
0.8722	High Similarity	NPC231572
0.8333	Intermediate Similarity	NPC321133
0.8254	Intermediate Similarity	NPC43275
0.8162	Intermediate Similarity	NPC307682
0.812	Intermediate Similarity	NPC120251
0.8047	Intermediate Similarity	NPC263835
0.8045	Intermediate Similarity	NPC283079
0.8029	Intermediate Similarity	NPC99078
0.8028	Intermediate Similarity	NPC296085
0.8016	Intermediate Similarity	NPC19290
0.8015	Intermediate Similarity	NPC473360
0.7971	Intermediate Similarity	NPC252107
0.7971	Intermediate Similarity	NPC220923
0.7971	Intermediate Similarity	NPC470707
0.7971	Intermediate Similarity	NPC193528
0.7958	Intermediate Similarity	NPC9373
0.7956	Intermediate Similarity	NPC255817
0.7956	Intermediate Similarity	NPC277042
0.7956	Intermediate Similarity	NPC73883
0.7956	Intermediate Similarity	NPC136330
0.7956	Intermediate Similarity	NPC196609
0.7956	Intermediate Similarity	NPC230698
0.7956	Intermediate Similarity	NPC251454
0.7956	Intermediate Similarity	NPC205178
0.7934	Intermediate Similarity	NPC113457
0.7902	Intermediate Similarity	NPC71629
0.7883	Intermediate Similarity	NPC29650
0.7883	Intermediate Similarity	NPC167096
0.7879	Intermediate Similarity	NPC62101
0.7879	Intermediate Similarity	NPC95733
0.7836	Intermediate Similarity	NPC172403
0.7836	Intermediate Similarity	NPC251571
0.7826	Intermediate Similarity	NPC96406
0.7826	Intermediate Similarity	NPC138365
0.782	Intermediate Similarity	NPC29477
0.7815	Intermediate Similarity	NPC289381
0.7815	Intermediate Similarity	NPC155847
0.7805	Intermediate Similarity	NPC201959
0.7803	Intermediate Similarity	NPC211218
0.7795	Intermediate Similarity	NPC296526
0.7795	Intermediate Similarity	NPC303370
0.7794	Intermediate Similarity	NPC257390
0.7778	Intermediate Similarity	NPC155838
0.777	Intermediate Similarity	NPC145446
0.777	Intermediate Similarity	NPC137172
0.7769	Intermediate Similarity	NPC41801
0.776	Intermediate Similarity	NPC166837
0.7754	Intermediate Similarity	NPC193673
0.7754	Intermediate Similarity	NPC328419
0.7754	Intermediate Similarity	NPC45783
0.7754	Intermediate Similarity	NPC94280
0.7754	Intermediate Similarity	NPC103947
0.7754	Intermediate Similarity	NPC159150
0.7744	Intermediate Similarity	NPC171372
0.7727	Intermediate Similarity	NPC471314
0.7727	Intermediate Similarity	NPC471315
0.7721	Intermediate Similarity	NPC35961
0.7721	Intermediate Similarity	NPC52029
0.7721	Intermediate Similarity	NPC195749
0.7714	Intermediate Similarity	NPC95366
0.7714	Intermediate Similarity	NPC113236
0.7714	Intermediate Similarity	NPC248505
0.7714	Intermediate Similarity	NPC214036
0.771	Intermediate Similarity	NPC83279
0.771	Intermediate Similarity	NPC131868
0.7703	Intermediate Similarity	NPC471073
0.7703	Intermediate Similarity	NPC270811
0.7698	Intermediate Similarity	NPC237227
0.7681	Intermediate Similarity	NPC132308
0.7681	Intermediate Similarity	NPC169766
0.7664	Intermediate Similarity	NPC114102
0.7661	Intermediate Similarity	NPC24101
0.7661	Intermediate Similarity	NPC75440
0.7661	Intermediate Similarity	NPC96224
0.7652	Intermediate Similarity	NPC251259
0.763	Intermediate Similarity	NPC301713
0.7623	Intermediate Similarity	NPC2518
0.7623	Intermediate Similarity	NPC474603
0.7623	Intermediate Similarity	NPC12987
0.7609	Intermediate Similarity	NPC214869
0.7609	Intermediate Similarity	NPC118419
0.7609	Intermediate Similarity	NPC217574
0.7589	Intermediate Similarity	NPC471316
0.7586	Intermediate Similarity	NPC185838
0.7581	Intermediate Similarity	NPC260952
0.7576	Intermediate Similarity	NPC269843
0.7576	Intermediate Similarity	NPC318357
0.7576	Intermediate Similarity	NPC189844
0.7576	Intermediate Similarity	NPC60962
0.7576	Intermediate Similarity	NPC14007
0.7576	Intermediate Similarity	NPC224814
0.7576	Intermediate Similarity	NPC109083
0.7574	Intermediate Similarity	NPC17374
0.7561	Intermediate Similarity	NPC42383
0.7557	Intermediate Similarity	NPC256369
0.754	Intermediate Similarity	NPC183700
0.7538	Intermediate Similarity	NPC280001
0.7538	Intermediate Similarity	NPC323948
0.7537	Intermediate Similarity	NPC307020
0.752	Intermediate Similarity	NPC206341
0.75	Intermediate Similarity	NPC53596
0.75	Intermediate Similarity	NPC289330
0.75	Intermediate Similarity	NPC201967
0.75	Intermediate Similarity	NPC908
0.75	Intermediate Similarity	NPC141003
0.75	Intermediate Similarity	NPC17388
0.75	Intermediate Similarity	NPC231705
0.75	Intermediate Similarity	NPC138438
0.75	Intermediate Similarity	NPC35344
0.75	Intermediate Similarity	NPC471308
0.75	Intermediate Similarity	NPC470441
0.75	Intermediate Similarity	NPC160120
0.75	Intermediate Similarity	NPC175298
0.7483	Intermediate Similarity	NPC324081
0.7483	Intermediate Similarity	NPC321505
0.7483	Intermediate Similarity	NPC191376
0.7483	Intermediate Similarity	NPC476151
0.7483	Intermediate Similarity	NPC319320
0.7483	Intermediate Similarity	NPC287757
0.7483	Intermediate Similarity	NPC179825
0.7465	Intermediate Similarity	NPC225745
0.746	Intermediate Similarity	NPC474272
0.7447	Intermediate Similarity	NPC196708
0.7447	Intermediate Similarity	NPC11147
0.7447	Intermediate Similarity	NPC180647
0.7445	Intermediate Similarity	NPC186898
0.7445	Intermediate Similarity	NPC153990
0.744	Intermediate Similarity	NPC142297
0.7438	Intermediate Similarity	NPC130193
0.7432	Intermediate Similarity	NPC428
0.7432	Intermediate Similarity	NPC246587
0.7432	Intermediate Similarity	NPC476571
0.7432	Intermediate Similarity	NPC135538
0.7432	Intermediate Similarity	NPC147390
0.7432	Intermediate Similarity	NPC24233
0.7432	Intermediate Similarity	NPC153644
0.7422	Intermediate Similarity	NPC199462
0.7413	Intermediate Similarity	NPC476989
0.7413	Intermediate Similarity	NPC150712
0.7407	Intermediate Similarity	NPC18984
0.7407	Intermediate Similarity	NPC106659
0.7407	Intermediate Similarity	NPC328267
0.7407	Intermediate Similarity	NPC229084
0.7407	Intermediate Similarity	NPC160900
0.7403	Intermediate Similarity	NPC135006
0.7398	Intermediate Similarity	NPC178902
0.7394	Intermediate Similarity	NPC131204
0.7394	Intermediate Similarity	NPC301050
0.7388	Intermediate Similarity	NPC268348
0.7385	Intermediate Similarity	NPC185541
0.7385	Intermediate Similarity	NPC464
0.7383	Intermediate Similarity	NPC477565
0.7383	Intermediate Similarity	NPC103379
0.7381	Intermediate Similarity	NPC146530
0.7381	Intermediate Similarity	NPC97811
0.7381	Intermediate Similarity	NPC153690
0.7377	Intermediate Similarity	NPC13755
0.7377	Intermediate Similarity	NPC253746
0.7372	Intermediate Similarity	NPC120225
0.7372	Intermediate Similarity	NPC213552
0.7372	Intermediate Similarity	NPC179777
0.7372	Intermediate Similarity	NPC305717
0.7361	Intermediate Similarity	NPC212850
0.7361	Intermediate Similarity	NPC189724
0.7361	Intermediate Similarity	NPC83289
0.736	Intermediate Similarity	NPC326447
0.7357	Intermediate Similarity	NPC318862
0.7357	Intermediate Similarity	NPC93882
0.7357	Intermediate Similarity	NPC130595
0.7353	Intermediate Similarity	NPC246704
0.7347	Intermediate Similarity	NPC189908
0.7346	Intermediate Similarity	NPC99723
0.7343	Intermediate Similarity	NPC312770
0.7343	Intermediate Similarity	NPC160607
0.7343	Intermediate Similarity	NPC41473
0.7343	Intermediate Similarity	NPC204848
0.7343	Intermediate Similarity	NPC28641
0.7343	Intermediate Similarity	NPC14600
0.7343	Intermediate Similarity	NPC194359
0.7328	Intermediate Similarity	NPC85292
0.7328	Intermediate Similarity	NPC54507
0.7328	Intermediate Similarity	NPC229147
0.7323	Intermediate Similarity	NPC79543
0.7323	Intermediate Similarity	NPC258056
0.7319	Intermediate Similarity	NPC151167
0.7319	Intermediate Similarity	NPC276466
0.7319	Intermediate Similarity	NPC123228
0.7319	Intermediate Similarity	NPC5018
0.7319	Intermediate Similarity	NPC123722
0.7308	Intermediate Similarity	NPC228287
0.7308	Intermediate Similarity	NPC180508
0.7308	Intermediate Similarity	NPC114144
0.7305	Intermediate Similarity	NPC313737
0.7305	Intermediate Similarity	NPC6854
0.7305	Intermediate Similarity	NPC285078
0.7302	Intermediate Similarity	NPC151530
0.7302	Intermediate Similarity	NPC157473
0.7299	Intermediate Similarity	NPC289459
0.7299	Intermediate Similarity	NPC87113

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 NPC218323 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	130
0.1-0.2	699
0.2-0.3	1024
0.3-0.4	1652
0.4-0.5	2538
0.5-0.6	2030
0.6-0.7	930
0.7-0.8	145
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
0.8333	Intermediate Similarity	NPD2667	Approved
0.8333	Intermediate Similarity	NPD2668	Approved
0.8201	Intermediate Similarity	NPD5481	Discontinued
0.8047	Intermediate Similarity	NPD2423	Clinical (unspecified phase)
0.7956	Intermediate Similarity	NPD2492	Phase 1
0.7939	Intermediate Similarity	NPD6582	Phase 2
0.7939	Intermediate Similarity	NPD6583	Phase 3
0.7863	Intermediate Similarity	NPD2232	Approved
0.7863	Intermediate Similarity	NPD2233	Approved
0.7863	Intermediate Similarity	NPD2230	Approved
0.7862	Intermediate Similarity	NPD7131	Phase 3
0.7852	Intermediate Similarity	NPD5163	Phase 2
0.7829	Intermediate Similarity	NPD2594	Approved
0.7829	Intermediate Similarity	NPD2595	Approved
0.7826	Intermediate Similarity	NPD3052	Approved
0.7826	Intermediate Similarity	NPD3054	Approved
0.7778	Intermediate Similarity	NPD2228	Approved
0.7778	Intermediate Similarity	NPD2234	Approved
0.7778	Intermediate Similarity	NPD2229	Approved
0.777	Intermediate Similarity	NPD743	Approved
0.7761	Intermediate Similarity	NPD6584	Phase 3
0.7755	Intermediate Similarity	NPD824	Approved
0.7752	Intermediate Similarity	NPD2486	Discontinued
0.7744	Intermediate Similarity	NPD7258	Clinical (unspecified phase)
0.7734	Intermediate Similarity	NPD3596	Phase 2
0.771	Intermediate Similarity	NPD3294	Phase 2
0.7698	Intermediate Similarity	NPD4579	Clinical (unspecified phase)
0.7681	Intermediate Similarity	NPD3140	Approved
0.7681	Intermediate Similarity	NPD3142	Approved
0.7664	Intermediate Similarity	NPD3374	Clinical (unspecified phase)
0.7664	Intermediate Similarity	NPD3056	Clinical (unspecified phase)
0.7647	Intermediate Similarity	NPD5752	Clinical (unspecified phase)
0.7634	Intermediate Similarity	NPD5238	Clinical (unspecified phase)
0.7619	Intermediate Similarity	NPD1670	Discontinued
0.7609	Intermediate Similarity	NPD5745	Approved
0.7557	Intermediate Similarity	NPD4093	Discontinued
0.7557	Intermediate Similarity	NPD6382	Discontinued
0.7537	Intermediate Similarity	NPD1421	Approved
0.7537	Intermediate Similarity	NPD1420	Approved
0.7537	Intermediate Similarity	NPD4659	Approved
0.7537	Intermediate Similarity	NPD1669	Approved
0.7536	Intermediate Similarity	NPD5718	Phase 2
0.7535	Intermediate Similarity	NPD1725	Approved
0.7518	Intermediate Similarity	NPD4207	Discontinued
0.75	Intermediate Similarity	NPD2976	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD3060	Approved
0.75	Intermediate Similarity	NPD7905	Discontinued
0.7483	Intermediate Similarity	NPD5865	Clinical (unspecified phase)
0.7483	Intermediate Similarity	NPD3536	Discontinued
0.7482	Intermediate Similarity	NPD2245	Discovery
0.7481	Intermediate Similarity	NPD5303	Approved
0.7481	Intermediate Similarity	NPD5304	Approved
0.7481	Intermediate Similarity	NPD6581	Approved
0.7481	Intermediate Similarity	NPD6580	Approved
0.7466	Intermediate Similarity	NPD3281	Clinical (unspecified phase)
0.7466	Intermediate Similarity	NPD6666	Approved
0.7466	Intermediate Similarity	NPD6667	Approved
0.7464	Intermediate Similarity	NPD5746	Approved
0.7463	Intermediate Similarity	NPD2562	Approved
0.7463	Intermediate Similarity	NPD2561	Approved
0.7452	Intermediate Similarity	NPD3451	Clinical (unspecified phase)
0.7444	Intermediate Similarity	NPD3447	Discontinued
0.7444	Intermediate Similarity	NPD3847	Discontinued
0.7429	Intermediate Similarity	NPD2238	Phase 2
0.7426	Intermediate Similarity	NPD4104	Clinical (unspecified phase)
0.7426	Intermediate Similarity	NPD4098	Discontinued
0.7426	Intermediate Similarity	NPD4103	Phase 2
0.7424	Intermediate Similarity	NPD6830	Clinical (unspecified phase)
0.7415	Intermediate Similarity	NPD5297	Approved
0.7407	Intermediate Similarity	NPD3676	Clinical (unspecified phase)
0.7407	Intermediate Similarity	NPD2428	Approved
0.7407	Intermediate Similarity	NPD2429	Approved
0.7407	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7397	Intermediate Similarity	NPD5241	Discontinued
0.7386	Intermediate Similarity	NPD5967	Approved
0.7385	Intermediate Similarity	NPD2557	Approved
0.7383	Intermediate Similarity	NPD6662	Clinical (unspecified phase)
0.7372	Intermediate Similarity	NPD2990	Approved
0.7372	Intermediate Similarity	NPD7018	Phase 2
0.7372	Intermediate Similarity	NPD2987	Approved
0.7368	Intermediate Similarity	NPD2554	Approved
0.7368	Intermediate Similarity	NPD7577	Discontinued
0.7368	Intermediate Similarity	NPD2556	Approved
0.7365	Intermediate Similarity	NPD2335	Discontinued
0.736	Intermediate Similarity	NPD3134	Approved
0.7357	Intermediate Similarity	NPD2674	Phase 3
0.7347	Intermediate Similarity	NPD6884	Clinical (unspecified phase)
0.7323	Intermediate Similarity	NPD1792	Phase 2
0.7319	Intermediate Similarity	NPD4993	Discontinued
0.7319	Intermediate Similarity	NPD4208	Discontinued
0.731	Intermediate Similarity	NPD3655	Clinical (unspecified phase)
0.731	Intermediate Similarity	NPD7037	Approved
0.7308	Intermediate Similarity	NPD595	Approved
0.7308	Intermediate Similarity	NPD593	Approved
0.7297	Intermediate Similarity	NPD7213	Phase 3
0.7297	Intermediate Similarity	NPD7212	Phase 2
0.7293	Intermediate Similarity	NPD3445	Approved
0.7293	Intermediate Similarity	NPD3443	Approved
0.7293	Intermediate Similarity	NPD3444	Approved
0.7293	Intermediate Similarity	NPD3049	Approved
0.7292	Intermediate Similarity	NPD4476	Approved
0.7292	Intermediate Similarity	NPD4477	Approved
0.729	Intermediate Similarity	NPD8031	Discontinued
0.7286	Intermediate Similarity	NPD3144	Approved
0.7286	Intermediate Similarity	NPD3145	Approved
0.7279	Intermediate Similarity	NPD6542	Approved
0.7279	Intermediate Similarity	NPD6540	Phase 3
0.7279	Intermediate Similarity	NPD6543	Approved
0.7279	Intermediate Similarity	NPD6539	Approved
0.7278	Intermediate Similarity	NPD2388	Discontinued
0.7273	Intermediate Similarity	NPD6895	Approved
0.7273	Intermediate Similarity	NPD16	Approved
0.7273	Intermediate Similarity	NPD856	Approved
0.7273	Intermediate Similarity	NPD6896	Approved
0.7267	Intermediate Similarity	NPD5441	Clinical (unspecified phase)
0.7267	Intermediate Similarity	NPD5586	Clinical (unspecified phase)
0.726	Intermediate Similarity	NPD2458	Approved
0.726	Intermediate Similarity	NPD5177	Phase 3
0.726	Intermediate Similarity	NPD2459	Approved
0.726	Intermediate Similarity	NPD6364	Approved
0.726	Intermediate Similarity	NPD2460	Phase 3
0.726	Intermediate Similarity	NPD44	Approved
0.725	Intermediate Similarity	NPD5940	Clinical (unspecified phase)
0.725	Intermediate Similarity	NPD2934	Approved
0.725	Intermediate Similarity	NPD2933	Approved
0.7248	Intermediate Similarity	NPD7447	Phase 1
0.7234	Intermediate Similarity	NPD7477	Discontinued
0.7233	Intermediate Similarity	NPD6894	Phase 1
0.7222	Intermediate Similarity	NPD1445	Approved
0.7222	Intermediate Similarity	NPD1444	Approved
0.7218	Intermediate Similarity	NPD2226	Clinical (unspecified phase)
0.7206	Intermediate Similarity	NPD2235	Phase 2
0.7206	Intermediate Similarity	NPD2231	Phase 2
0.7192	Intermediate Similarity	NPD4664	Clinical (unspecified phase)
0.719	Intermediate Similarity	NPD7109	Clinical (unspecified phase)
0.719	Intermediate Similarity	NPD2859	Approved
0.719	Intermediate Similarity	NPD7110	Phase 1
0.719	Intermediate Similarity	NPD2860	Approved
0.7188	Intermediate Similarity	NPD3366	Approved
0.7183	Intermediate Similarity	NPD3109	Approved
0.7183	Intermediate Similarity	NPD3110	Approved
0.7181	Intermediate Similarity	NPD4357	Discontinued
0.7174	Intermediate Similarity	NPD3055	Approved
0.7174	Intermediate Similarity	NPD3053	Approved
0.7165	Intermediate Similarity	NPD1358	Approved
0.7165	Intermediate Similarity	NPD5374	Approved
0.7165	Intermediate Similarity	NPD5373	Approved
0.7163	Intermediate Similarity	NPD6812	Clinical (unspecified phase)
0.7163	Intermediate Similarity	NPD1039	Discontinued
0.7154	Intermediate Similarity	NPD821	Approved
0.7152	Intermediate Similarity	NPD7427	Discontinued
0.7152	Intermediate Similarity	NPD1914	Approved
0.7143	Intermediate Similarity	NPD4236	Phase 3
0.7143	Intermediate Similarity	NPD4237	Approved
0.7143	Intermediate Similarity	NPD5536	Phase 2
0.7143	Intermediate Similarity	NPD4162	Approved
0.7143	Intermediate Similarity	NPD7177	Discontinued
0.7143	Intermediate Similarity	NPD2614	Approved
0.7134	Intermediate Similarity	NPD8245	Clinical (unspecified phase)
0.7132	Intermediate Similarity	NPD5351	Clinical (unspecified phase)
0.7132	Intermediate Similarity	NPD5350	Clinical (unspecified phase)
0.7124	Intermediate Similarity	NPD6876	Approved
0.7124	Intermediate Similarity	NPD1337	Clinical (unspecified phase)
0.7124	Intermediate Similarity	NPD6875	Approved
0.7123	Intermediate Similarity	NPD7030	Discontinued
0.7123	Intermediate Similarity	NPD3656	Approved
0.7114	Intermediate Similarity	NPD160	Clinical (unspecified phase)
0.7114	Intermediate Similarity	NPD5295	Discontinued
0.7113	Intermediate Similarity	NPD4475	Approved
0.7113	Intermediate Similarity	NPD4474	Approved
0.7111	Intermediate Similarity	NPD1751	Approved
0.7107	Intermediate Similarity	NPD5186	Approved
0.7107	Intermediate Similarity	NPD5183	Approved
0.7103	Intermediate Similarity	NPD6029	Clinical (unspecified phase)
0.7103	Intermediate Similarity	NPD6028	Clinical (unspecified phase)
0.7103	Intermediate Similarity	NPD6380	Phase 1
0.7103	Intermediate Similarity	NPD1753	Discontinued
0.7101	Intermediate Similarity	NPD196	Phase 1
0.7101	Intermediate Similarity	NPD5311	Approved
0.7101	Intermediate Similarity	NPD5310	Approved
0.7101	Intermediate Similarity	NPD6538	Approved
0.7101	Intermediate Similarity	NPD6541	Approved
0.7092	Intermediate Similarity	NPD6179	Discontinued
0.7092	Intermediate Similarity	NPD2669	Clinical (unspecified phase)
0.7089	Intermediate Similarity	NPD2042	Clinical (unspecified phase)
0.7089	Intermediate Similarity	NPD2904	Discontinued
0.7089	Intermediate Similarity	NPD2041	Clinical (unspecified phase)
0.7087	Intermediate Similarity	NPD968	Approved
0.7086	Intermediate Similarity	NPD1975	Clinical (unspecified phase)
0.7086	Intermediate Similarity	NPD6090	Discontinued
0.7078	Intermediate Similarity	NPD6385	Approved
0.7078	Intermediate Similarity	NPD6386	Approved
0.7078	Intermediate Similarity	NPD6873	Phase 2
0.7075	Intermediate Similarity	NPD7596	Clinical (unspecified phase)
0.7071	Intermediate Similarity	NPD3636	Approved
0.7071	Intermediate Similarity	NPD3635	Approved
0.7071	Intermediate Similarity	NPD3637	Approved
0.707	Intermediate Similarity	NPD6533	Clinical (unspecified phase)
0.707	Intermediate Similarity	NPD8005	Clinical (unspecified phase)
0.7063	Intermediate Similarity	NPD9610	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