NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	402.93
Volume:	271.092
LogP:	1.19
LogD:	1.138
LogS:	-3.081
# Rotatable Bonds:	1
TPSA:	120.55
# H-Bond Aceptor:	7
# H-Bond Donor:	6
# Rings:	3
# Heavy Atoms:	9

MedChem Properties

QED Drug-Likeness Score:	0.433
Synthetic Accessibility Score:	4.471
Fsp3:	0.273
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:	-5.69
MDCK Permeability:	1.0043198926723562e-05
Pgp-inhibitor:	0.001
Pgp-substrate:	0.016
Human Intestinal Absorption (HIA):	0.977
20% Bioavailability (F20%):	0.044
30% Bioavailability (F30%):	0.003

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.339
Plasma Protein Binding (PPB):	93.11841583251953%
Volume Distribution (VD):	0.661
Pgp-substrate:	9.26539421081543%

ADMET: Metabolism

CYP1A2-inhibitor:	0.039
CYP1A2-substrate:	0.711
CYP2C19-inhibitor:	0.433
CYP2C19-substrate:	0.035
CYP2C9-inhibitor:	0.301
CYP2C9-substrate:	0.011
CYP2D6-inhibitor:	0.003
CYP2D6-substrate:	0.034
CYP3A4-inhibitor:	0.527
CYP3A4-substrate:	0.507

ADMET: Excretion

Clearance (CL):	3.412
Half-life (T1/2):	0.857

ADMET: Toxicity

hERG Blockers:	0.279
Human Hepatotoxicity (H-HT):	0.979
Drug-inuced Liver Injury (DILI):	0.963
AMES Toxicity:	0.122
Rat Oral Acute Toxicity:	0.988
Maximum Recommended Daily Dose:	0.872
Skin Sensitization:	0.23
Carcinogencity:	0.916
Eye Corrosion:	0.003
Eye Irritation:	0.01
Respiratory Toxicity:	0.979

Download Data

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

Natural Product: NPC474696

Natural Product ID:	NPC474696
*Common Name:**	Spongiacidin A
IUPAC Name:	(4E)-4-(2-amino-5-oxoimidazolidin-4-ylidene)-2,3-dibromo-1,5,6,7-tetrahydropyrrolo[2,3-c]azepin-8-one
Synonyms:
Standard InCHIKey:	CTHGIINQRBTFRV-ZZXKWVIFSA-N
Standard InCHI:	InChI=1S/C11H11Br2N5O2/c12-5-4-3(6-10(20)18-11(14)17-6)1-2-15-9(19)7(4)16-8(5)13/h11,16-17H,1-2,14H2,(H,15,19)(H,18,20)/b6-3+
SMILES:	C1CNC(=O)C2=C(C1=C3C(=O)NC(N3)N)C(=C(N2)Br)Br
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL479512
PubChem CID:	44575454
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0001990] Pyrroloazepines

*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
NPO32740	hymeniacidon sp.	Species	Halichondriidae	Eukaryota	n.a.	southern Australian	n.a.	PMID[11908980]
NPO32740	hymeniacidon sp.	Species	Halichondriidae	Eukaryota	n.a.	Singapore	n.a.	PMID[15043446]
NPO32740	hymeniacidon sp.	Species	Halichondriidae	Eukaryota	n.a.	n.a.	n.a.	PMID[9599282]

☑ 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
Individual Protein	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT286	Individual Protein	Receptor protein-tyrosine kinase erbB-2	Homo sapiens	IC50	=	8.5	ug.mL-1	PMID[493487]
NPT2213	Individual Protein	Cyclin-dependent kinase 4	Homo sapiens	IC50	=	32.0	ug.mL-1	PMID[493487]

☑ 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 NPC474696 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	749
0.1-0.2	12699
0.2-0.3	20415
0.3-0.4	4129
0.4-0.5	3182
0.5-0.6	1306
0.6-0.7	169
0.7-0.8	41
0.8-0.85	2
0.85-0.9	1
0.9-0.95	2
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9742	High Similarity	NPC271927
0.9141	High Similarity	NPC184932
0.9141	High Similarity	NPC472861
0.9068	High Similarity	NPC37268
0.8827	High Similarity	NPC469976
0.8519	High Similarity	NPC73687
0.8214	Intermediate Similarity	NPC80528
0.8024	Intermediate Similarity	NPC2414
0.7857	Intermediate Similarity	NPC206148
0.7647	Intermediate Similarity	NPC476418
0.75	Intermediate Similarity	NPC260041
0.75	Intermediate Similarity	NPC19342
0.7459	Intermediate Similarity	NPC63571
0.7459	Intermediate Similarity	NPC111566
0.7418	Intermediate Similarity	NPC310633
0.7401	Intermediate Similarity	NPC136441
0.7396	Intermediate Similarity	NPC474236
0.7345	Intermediate Similarity	NPC97106
0.733	Intermediate Similarity	NPC54214
0.7316	Intermediate Similarity	NPC9635
0.7312	Intermediate Similarity	NPC150592
0.731	Intermediate Similarity	NPC27296
0.7308	Intermediate Similarity	NPC474258
0.7302	Intermediate Similarity	NPC19696
0.7302	Intermediate Similarity	NPC136957
0.7296	Intermediate Similarity	NPC469715
0.7286	Intermediate Similarity	NPC469717
0.7234	Intermediate Similarity	NPC48117
0.7234	Intermediate Similarity	NPC476526
0.7234	Intermediate Similarity	NPC329765
0.7209	Intermediate Similarity	NPC475870
0.72	Intermediate Similarity	NPC233380
0.7196	Intermediate Similarity	NPC475286
0.7196	Intermediate Similarity	NPC174281
0.7166	Intermediate Similarity	NPC476413
0.7158	Intermediate Similarity	NPC469814
0.7151	Intermediate Similarity	NPC186068
0.7143	Intermediate Similarity	NPC20021
0.7135	Intermediate Similarity	NPC476421
0.7135	Intermediate Similarity	NPC227489
0.7135	Intermediate Similarity	NPC473946
0.7135	Intermediate Similarity	NPC28096
0.7128	Intermediate Similarity	NPC476414
0.712	Intermediate Similarity	NPC476423
0.7102	Intermediate Similarity	NPC474383
0.7092	Intermediate Similarity	NPC476524
0.7045	Intermediate Similarity	NPC306160
0.7039	Intermediate Similarity	NPC226835
0.6932	Remote Similarity	NPC473706
0.6923	Remote Similarity	NPC469716
0.6919	Remote Similarity	NPC52110
0.6919	Remote Similarity	NPC476525
0.6898	Remote Similarity	NPC112489
0.6898	Remote Similarity	NPC46022
0.676	Remote Similarity	NPC274981
0.6758	Remote Similarity	NPC302647
0.6755	Remote Similarity	NPC311282
0.6737	Remote Similarity	NPC473628
0.6736	Remote Similarity	NPC46811
0.672	Remote Similarity	NPC476527
0.6615	Remote Similarity	NPC475874
0.6599	Remote Similarity	NPC477004
0.6573	Remote Similarity	NPC142688
0.6553	Remote Similarity	NPC50562
0.6548	Remote Similarity	NPC474389
0.6543	Remote Similarity	NPC234403
0.6534	Remote Similarity	NPC471655
0.6522	Remote Similarity	NPC67658
0.65	Remote Similarity	NPC474492
0.6497	Remote Similarity	NPC109158
0.6455	Remote Similarity	NPC79777
0.6429	Remote Similarity	NPC188821
0.6429	Remote Similarity	NPC474180
0.641	Remote Similarity	NPC243716
0.6406	Remote Similarity	NPC133003
0.6393	Remote Similarity	NPC162268
0.6381	Remote Similarity	NPC475736
0.6374	Remote Similarity	NPC100104
0.6374	Remote Similarity	NPC470680
0.6368	Remote Similarity	NPC314281
0.6368	Remote Similarity	NPC40530
0.6354	Remote Similarity	NPC212742
0.6318	Remote Similarity	NPC13456
0.6318	Remote Similarity	NPC77241
0.6318	Remote Similarity	NPC269203
0.6318	Remote Similarity	NPC166209
0.6316	Remote Similarity	NPC11126
0.6313	Remote Similarity	NPC472260
0.6287	Remote Similarity	NPC471944
0.6283	Remote Similarity	NPC91179
0.6283	Remote Similarity	NPC182940
0.6281	Remote Similarity	NPC77061
0.6276	Remote Similarity	NPC324091
0.6269	Remote Similarity	NPC475914
0.6269	Remote Similarity	NPC153123
0.6269	Remote Similarity	NPC268744
0.6269	Remote Similarity	NPC220797
0.6269	Remote Similarity	NPC477003
0.6269	Remote Similarity	NPC201266
0.6269	Remote Similarity	NPC474318
0.6268	Remote Similarity	NPC470703
0.6264	Remote Similarity	NPC299594
0.6262	Remote Similarity	NPC243633
0.6262	Remote Similarity	NPC175150
0.6243	Remote Similarity	NPC33229
0.6237	Remote Similarity	NPC109447
0.6223	Remote Similarity	NPC262338
0.622	Remote Similarity	NPC470702
0.622	Remote Similarity	NPC473218
0.6218	Remote Similarity	NPC470205
0.6214	Remote Similarity	NPC270918
0.6203	Remote Similarity	NPC46359
0.6201	Remote Similarity	NPC13432
0.62	Remote Similarity	NPC179701
0.6197	Remote Similarity	NPC168209
0.619	Remote Similarity	NPC161861
0.6188	Remote Similarity	NPC237414
0.6186	Remote Similarity	NPC228835
0.6184	Remote Similarity	NPC143075
0.6181	Remote Similarity	NPC477414
0.6181	Remote Similarity	NPC221726
0.6181	Remote Similarity	NPC225622
0.6173	Remote Similarity	NPC17059
0.6169	Remote Similarity	NPC262898
0.6168	Remote Similarity	NPC474195
0.6165	Remote Similarity	NPC471191
0.6163	Remote Similarity	NPC291517
0.6162	Remote Similarity	NPC210123
0.6162	Remote Similarity	NPC26491
0.6154	Remote Similarity	NPC298288
0.615	Remote Similarity	NPC49217
0.6145	Remote Similarity	NPC100726
0.6136	Remote Similarity	NPC114033
0.6136	Remote Similarity	NPC101130
0.6136	Remote Similarity	NPC58268
0.6136	Remote Similarity	NPC129412
0.6129	Remote Similarity	NPC271734
0.6126	Remote Similarity	NPC151635
0.6122	Remote Similarity	NPC141612
0.6122	Remote Similarity	NPC135601
0.6122	Remote Similarity	NPC94752
0.6122	Remote Similarity	NPC17273
0.6119	Remote Similarity	NPC102592
0.6119	Remote Similarity	NPC79356
0.6119	Remote Similarity	NPC156003
0.6114	Remote Similarity	NPC66642
0.6111	Remote Similarity	NPC102664
0.6105	Remote Similarity	NPC64055
0.6103	Remote Similarity	NPC110158
0.6094	Remote Similarity	NPC240088
0.6094	Remote Similarity	NPC15573
0.6094	Remote Similarity	NPC217372
0.6094	Remote Similarity	NPC473380
0.6094	Remote Similarity	NPC183662
0.6093	Remote Similarity	NPC272174
0.6085	Remote Similarity	NPC471943
0.608	Remote Similarity	NPC476460
0.6077	Remote Similarity	NPC473878
0.6069	Remote Similarity	NPC23215
0.6068	Remote Similarity	NPC317701
0.6062	Remote Similarity	NPC219336
0.6062	Remote Similarity	NPC265710
0.6061	Remote Similarity	NPC209917
0.6056	Remote Similarity	NPC470732
0.6055	Remote Similarity	NPC474196
0.605	Remote Similarity	NPC304187
0.605	Remote Similarity	NPC477166
0.6043	Remote Similarity	NPC247987
0.6042	Remote Similarity	NPC476419
0.6039	Remote Similarity	NPC473376
0.6034	Remote Similarity	NPC14448
0.6034	Remote Similarity	NPC195704
0.6034	Remote Similarity	NPC98156
0.6034	Remote Similarity	NPC470440
0.6034	Remote Similarity	NPC167200
0.6034	Remote Similarity	NPC292434
0.6034	Remote Similarity	NPC138596
0.6034	Remote Similarity	NPC200397
0.6034	Remote Similarity	NPC64661
0.6033	Remote Similarity	NPC74357
0.6031	Remote Similarity	NPC477042
0.6031	Remote Similarity	NPC16659
0.6022	Remote Similarity	NPC123906
0.602	Remote Similarity	NPC21429
0.602	Remote Similarity	NPC473821
0.6011	Remote Similarity	NPC232798
0.601	Remote Similarity	NPC74153
0.601	Remote Similarity	NPC141454
0.6	Remote Similarity	NPC213914
0.5991	Remote Similarity	NPC471194
0.5991	Remote Similarity	NPC471193
0.5991	Remote Similarity	NPC474896
0.599	Remote Similarity	NPC202812
0.599	Remote Similarity	NPC469529
0.5989	Remote Similarity	NPC244087
0.5989	Remote Similarity	NPC205604
0.5989	Remote Similarity	NPC48171
0.5989	Remote Similarity	NPC286529
0.5989	Remote Similarity	NPC169308
0.5989	Remote Similarity	NPC77582

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 NPC474696 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	256
0.1-0.2	930
0.2-0.3	1491
0.3-0.4	2828
0.4-0.5	2885
0.5-0.6	741
0.6-0.7	19
0.7-0.8	0
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
0.658	Remote Similarity	NPD5592	Clinical (unspecified phase)
0.6531	Remote Similarity	NPD2290	Phase 3
0.6531	Remote Similarity	NPD2289	Phase 3
0.6508	Remote Similarity	NPD3178	Discontinued
0.644	Remote Similarity	NPD1096	Discontinued
0.6335	Remote Similarity	NPD1783	Clinical (unspecified phase)
0.6319	Remote Similarity	NPD2213	Approved
0.6319	Remote Similarity	NPD2214	Approved
0.6298	Remote Similarity	NPD276	Clinical (unspecified phase)
0.6219	Remote Similarity	NPD7459	Phase 2
0.6218	Remote Similarity	NPD3318	Approved
0.6218	Remote Similarity	NPD3319	Phase 1
0.6218	Remote Similarity	NPD3320	Approved
0.6207	Remote Similarity	NPD569	Clinical (unspecified phase)
0.6106	Remote Similarity	NPD6376	Discontinued
0.6093	Remote Similarity	NPD1996	Discontinued
0.6091	Remote Similarity	NPD6141	Clinical (unspecified phase)
0.6041	Remote Similarity	NPD5820	Clinical (unspecified phase)
0.5991	Remote Similarity	NPD3918	Approved
0.5991	Remote Similarity	NPD3917	Approved
0.5991	Remote Similarity	NPD3916	Clinical (unspecified phase)
0.599	Remote Similarity	NPD4883	Approved
0.5963	Remote Similarity	NPD5001	Clinical (unspecified phase)
0.5962	Remote Similarity	NPD6288	Clinical (unspecified phase)
0.5961	Remote Similarity	NPD6449	Clinical (unspecified phase)
0.5957	Remote Similarity	NPD5140	Approved
0.5957	Remote Similarity	NPD5138	Approved
0.5956	Remote Similarity	NPD9343	Clinical (unspecified phase)
0.5947	Remote Similarity	NPD2844	Phase 3
0.5943	Remote Similarity	NPD3915	Approved
0.5941	Remote Similarity	NPD460	Discontinued
0.5911	Remote Similarity	NPD7618	Phase 3
0.5911	Remote Similarity	NPD7619	Phase 3
0.5907	Remote Similarity	NPD4736	Clinical (unspecified phase)
0.5905	Remote Similarity	NPD1506	Discontinued
0.5905	Remote Similarity	NPD8493	Clinical (unspecified phase)
0.5903	Remote Similarity	NPD3360	Clinical (unspecified phase)
0.59	Remote Similarity	NPD1284	Clinical (unspecified phase)
0.5894	Remote Similarity	NPD7817	Phase 1
0.5894	Remote Similarity	NPD5017	Discontinued
0.5877	Remote Similarity	NPD2443	Approved
0.5877	Remote Similarity	NPD2442	Approved
0.5871	Remote Similarity	NPD5686	Approved
0.5871	Remote Similarity	NPD5685	Approved
0.5866	Remote Similarity	NPD1592	Phase 3
0.5864	Remote Similarity	NPD7717	Approved
0.5864	Remote Similarity	NPD7716	Approved
0.5854	Remote Similarity	NPD1952	Discontinued
0.5853	Remote Similarity	NPD6578	Clinical (unspecified phase)
0.585	Remote Similarity	NPD3486	Clinical (unspecified phase)
0.5849	Remote Similarity	NPD2408	Discontinued
0.5849	Remote Similarity	NPD1600	Suspended
0.5842	Remote Similarity	NPD6180	Clinical (unspecified phase)
0.5841	Remote Similarity	NPD7656	Approved
0.5841	Remote Similarity	NPD7657	Approved
0.5838	Remote Similarity	NPD3990	Phase 3
0.5829	Remote Similarity	NPD6328	Clinical (unspecified phase)
0.5826	Remote Similarity	NPD5198	Approved
0.5826	Remote Similarity	NPD5199	Approved
0.5825	Remote Similarity	NPD482	Approved
0.5825	Remote Similarity	NPD465	Clinical (unspecified phase)
0.5825	Remote Similarity	NPD7204	Clinical (unspecified phase)
0.5817	Remote Similarity	NPD7727	Phase 2
0.5816	Remote Similarity	NPD2590	Clinical (unspecified phase)
0.5815	Remote Similarity	NPD4463	Approved
0.5815	Remote Similarity	NPD4462	Approved
0.5813	Remote Similarity	NPD4922	Phase 2
0.5795	Remote Similarity	NPD749	Clinical (unspecified phase)
0.5787	Remote Similarity	NPD3989	Phase 3
0.5787	Remote Similarity	NPD7971	Clinical (unspecified phase)
0.5787	Remote Similarity	NPD3757	Clinical (unspecified phase)
0.5787	Remote Similarity	NPD2323	Clinical (unspecified phase)
0.5787	Remote Similarity	NPD1643	Phase 3
0.5787	Remote Similarity	NPD7970	Approved
0.5784	Remote Similarity	NPD5965	Clinical (unspecified phase)
0.5778	Remote Similarity	NPD4464	Clinical (unspecified phase)
0.5778	Remote Similarity	NPD3834	Clinical (unspecified phase)
0.5775	Remote Similarity	NPD7704	Clinical (unspecified phase)
0.576	Remote Similarity	NPD3353	Approved
0.5755	Remote Similarity	NPD6838	Clinical (unspecified phase)
0.5755	Remote Similarity	NPD3410	Approved
0.5755	Remote Similarity	NPD3411	Phase 2
0.5751	Remote Similarity	NPD1573	Approved
0.5751	Remote Similarity	NPD1575	Approved
0.5749	Remote Similarity	NPD2947	Clinical (unspecified phase)
0.5748	Remote Similarity	NPD7998	Clinical (unspecified phase)
0.5744	Remote Similarity	NPD3522	Approved
0.5736	Remote Similarity	NPD3076	Approved
0.5736	Remote Similarity	NPD3077	Approved
0.5736	Remote Similarity	NPD3079	Approved
0.5736	Remote Similarity	NPD3078	Approved
0.5735	Remote Similarity	NPD8098	Approved
0.5735	Remote Similarity	NPD8114	Approved
0.5735	Remote Similarity	NPD8115	Approved
0.5721	Remote Similarity	NPD4426	Clinical (unspecified phase)
0.5721	Remote Similarity	NPD7621	Clinical (unspecified phase)
0.5721	Remote Similarity	NPD5809	Phase 3
0.5714	Remote Similarity	NPD6165	Phase 2
0.5714	Remote Similarity	NPD6164	Phase 2
0.5708	Remote Similarity	NPD4559	Clinical (unspecified phase)
0.5707	Remote Similarity	NPD5146	Suspended
0.5707	Remote Similarity	NPD1631	Approved
0.5707	Remote Similarity	NPD2004	Clinical (unspecified phase)
0.5701	Remote Similarity	NPD3968	Approved
0.5694	Remote Similarity	NPD8096	Phase 3
0.5694	Remote Similarity	NPD8097	Phase 3
0.5693	Remote Similarity	NPD3961	Discontinued
0.5693	Remote Similarity	NPD2009	Clinical (unspecified phase)
0.5691	Remote Similarity	NPD5020	Approved
0.5686	Remote Similarity	NPD1658	Discontinued
0.5685	Remote Similarity	NPD4092	Approved
0.5674	Remote Similarity	NPD7809	Clinical (unspecified phase)
0.5667	Remote Similarity	NPD7903	Clinical (unspecified phase)
0.5665	Remote Similarity	NPD1781	Discontinued
0.5662	Remote Similarity	NPD5643	Phase 2
0.5662	Remote Similarity	NPD1591	Approved
0.566	Remote Similarity	NPD2721	Clinical (unspecified phase)
0.5659	Remote Similarity	NPD7098	Clinical (unspecified phase)
0.5659	Remote Similarity	NPD6665	Discontinued
0.5657	Remote Similarity	NPD3998	Approved
0.5657	Remote Similarity	NPD3999	Approved
0.5657	Remote Similarity	NPD3997	Approved
0.565	Remote Similarity	NPD2095	Phase 2
0.565	Remote Similarity	NPD5728	Clinical (unspecified phase)
0.565	Remote Similarity	NPD2092	Phase 2
0.565	Remote Similarity	NPD2094	Phase 2
0.5648	Remote Similarity	NPD8013	Clinical (unspecified phase)
0.5646	Remote Similarity	NPD2405	Phase 3
0.564	Remote Similarity	NPD9540	Approved
0.5635	Remote Similarity	NPD4091	Approved
0.5634	Remote Similarity	NPD3967	Approved
0.5632	Remote Similarity	NPD1630	Approved
0.5628	Remote Similarity	NPD1618	Phase 2
0.5625	Remote Similarity	NPD6664	Approved
0.5622	Remote Similarity	NPD2096	Phase 2
0.5622	Remote Similarity	NPD8093	Discontinued
0.5622	Remote Similarity	NPD2091	Phase 2
0.5622	Remote Similarity	NPD3607	Clinical (unspecified phase)
0.5619	Remote Similarity	NPD5069	Clinical (unspecified phase)
0.5616	Remote Similarity	NPD3246	Discontinued
0.5614	Remote Similarity	NPD6263	Clinical (unspecified phase)
0.5606	Remote Similarity	NPD3993	Approved
0.5606	Remote Similarity	NPD3991	Approved
0.5606	Remote Similarity	NPD3996	Approved
0.5606	Remote Similarity	NPD3995	Approved
0.5606	Remote Similarity	NPD7865	Approved
0.5606	Remote Similarity	NPD3992	Approved
0.5606	Remote Similarity	NPD3994	Approved
0.5606	Remote Similarity	NPD3041	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