NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	416.19
Volume:	431.518
LogP:	1.855
LogD:	0.931
LogS:	-3.269
# Rotatable Bonds:	12
TPSA:	124.34
# H-Bond Aceptor:	8
# H-Bond Donor:	2
# Rings:	1
# Heavy Atoms:	8

MedChem Properties

QED Drug-Likeness Score:	0.322
Synthetic Accessibility Score:	3.47
Fsp3:	0.409
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:	-5.715
MDCK Permeability:	8.82483072928153e-06
Pgp-inhibitor:	0.002
Pgp-substrate:	0.008
Human Intestinal Absorption (HIA):	0.771
20% Bioavailability (F20%):	0.01
30% Bioavailability (F30%):	0.03

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.02
Plasma Protein Binding (PPB):	93.93700408935547%
Volume Distribution (VD):	0.284
Pgp-substrate:	2.3321750164031982%

ADMET: Metabolism

CYP1A2-inhibitor:	0.092
CYP1A2-substrate:	0.086
CYP2C19-inhibitor:	0.097
CYP2C19-substrate:	0.045
CYP2C9-inhibitor:	0.137
CYP2C9-substrate:	0.499
CYP2D6-inhibitor:	0.281
CYP2D6-substrate:	0.136
CYP3A4-inhibitor:	0.035
CYP3A4-substrate:	0.061

ADMET: Excretion

Clearance (CL):	1.329
Half-life (T1/2):	0.853

ADMET: Toxicity

hERG Blockers:	0.014
Human Hepatotoxicity (H-HT):	0.889
Drug-inuced Liver Injury (DILI):	0.973
AMES Toxicity:	0.021
Rat Oral Acute Toxicity:	0.057
Maximum Recommended Daily Dose:	0.012
Skin Sensitization:	0.101
Carcinogencity:	0.786
Eye Corrosion:	0.003
Eye Irritation:	0.013
Respiratory Toxicity:	0.081

Download Data

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

Natural Product: NPC478039

Natural Product ID:	NPC478039
*Common Name:**	(2S)-2-[[(2E,4E,6R)-7-[4-(dimethylamino)phenyl]-4,6-dimethyl-7-oxohepta-2,4-dienoyl]amino]pentanedioic acid
IUPAC Name:	(2S)-2-[[(2E,4E,6R)-7-[4-(dimethylamino)phenyl]-4,6-dimethyl-7-oxohepta-2,4-dienoyl]amino]pentanedioic acid
Synonyms:
Standard InCHIKey:	MROXIWXRMZGHLJ-DFYRDPISSA-N
Standard InCHI:	InChI=1S/C22H28N2O6/c1-14(5-11-19(25)23-18(22(29)30)10-12-20(26)27)13-15(2)21(28)16-6-8-17(9-7-16)24(3)4/h5-9,11,13,15,18H,10,12H2,1-4H3,(H,23,25)(H,26,27)(H,29,30)/b11-5+,14-13+/t15-,18+/m1/s1
SMILES:	C[C@H](/C=C(\C)/C=C/C(=O)N[C@@H](CCC(=O)O)C(=O)O)C(=O)C1=CC=C(C=C1)N(C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	n.a.
PubChem CID:	57331970
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000264] Organic acids and derivatives [CHEMONTID:0000265] Carboxylic acids and derivatives [CHEMONTID:0000013] Amino acids, peptides, and analogues [CHEMONTID:0000347] Amino acids and derivatives [CHEMONTID:0000060] Alpha amino acids and derivatives [CHEMONTID:0004323] Glutamic acid 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
NPO33673	Streptomyces sp. RM72	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[22276693]

☑ 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	1

Activity Type	# Activity
Individual Protein	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT684	Individual Protein	Histone deacetylase 1	Homo sapiens	IC50	=	48000	nM	PMID[22276693]

☑ 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 NPC478039 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	186
0.1-0.2	1447
0.2-0.3	6466
0.3-0.4	15011
0.4-0.5	14486
0.5-0.6	4435
0.6-0.7	632
0.7-0.8	23
0.8-0.85	6
0.85-0.9	4
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.8881	High Similarity	NPC314186
0.8824	High Similarity	NPC150863
0.8623	High Similarity	NPC472245
0.8623	High Similarity	NPC280807
0.8603	High Similarity	NPC472244
0.8603	High Similarity	NPC470343
0.8489	Intermediate Similarity	NPC314431
0.8345	Intermediate Similarity	NPC472243
0.8299	Intermediate Similarity	NPC478040
0.8108	Intermediate Similarity	NPC472241
0.8067	Intermediate Similarity	NPC472242
0.7862	Intermediate Similarity	NPC253667
0.7862	Intermediate Similarity	NPC35510
0.7818	Intermediate Similarity	NPC14849
0.7805	Intermediate Similarity	NPC248862
0.7793	Intermediate Similarity	NPC314098
0.777	Intermediate Similarity	NPC226143
0.7697	Intermediate Similarity	NPC328611
0.7665	Intermediate Similarity	NPC147298
0.7665	Intermediate Similarity	NPC131450
0.7665	Intermediate Similarity	NPC182057
0.7569	Intermediate Similarity	NPC205946
0.7483	Intermediate Similarity	NPC287358
0.7362	Intermediate Similarity	NPC27904
0.7358	Intermediate Similarity	NPC314223
0.7225	Intermediate Similarity	NPC470317
0.7214	Intermediate Similarity	NPC57051
0.7169	Intermediate Similarity	NPC189116
0.7162	Intermediate Similarity	NPC322433
0.7119	Intermediate Similarity	NPC316405
0.7115	Intermediate Similarity	NPC316202
0.7115	Intermediate Similarity	NPC43477
0.7086	Intermediate Similarity	NPC471742
0.7079	Intermediate Similarity	NPC313293
0.7059	Intermediate Similarity	NPC253476
0.7051	Intermediate Similarity	NPC242933
0.7048	Intermediate Similarity	NPC474058
0.7034	Intermediate Similarity	NPC177684
0.7034	Intermediate Similarity	NPC291962
0.7025	Intermediate Similarity	NPC314287
0.702	Intermediate Similarity	NPC194562
0.7019	Intermediate Similarity	NPC300596
0.7019	Intermediate Similarity	NPC237649
0.7006	Intermediate Similarity	NPC476231
0.7	Intermediate Similarity	NPC307437
0.7	Intermediate Similarity	NPC58827
0.7	Intermediate Similarity	NPC72473
0.6988	Remote Similarity	NPC36495
0.6986	Remote Similarity	NPC112373
0.6986	Remote Similarity	NPC161956
0.6986	Remote Similarity	NPC258531
0.6959	Remote Similarity	NPC318183
0.6957	Remote Similarity	NPC315829
0.6928	Remote Similarity	NPC153694
0.6928	Remote Similarity	NPC211525
0.6927	Remote Similarity	NPC471741
0.6894	Remote Similarity	NPC259678
0.6886	Remote Similarity	NPC154478
0.6879	Remote Similarity	NPC315224
0.6879	Remote Similarity	NPC319645
0.6871	Remote Similarity	NPC150323
0.6867	Remote Similarity	NPC84317
0.6824	Remote Similarity	NPC52059
0.6824	Remote Similarity	NPC257490
0.6824	Remote Similarity	NPC470069
0.6818	Remote Similarity	NPC475685
0.6815	Remote Similarity	NPC122553
0.6805	Remote Similarity	NPC199737
0.68	Remote Similarity	NPC474081
0.6792	Remote Similarity	NPC471574
0.6786	Remote Similarity	NPC310403
0.6786	Remote Similarity	NPC97380
0.6786	Remote Similarity	NPC243673
0.6786	Remote Similarity	NPC263709
0.6786	Remote Similarity	NPC148468
0.6786	Remote Similarity	NPC63210
0.6784	Remote Similarity	NPC472114
0.6784	Remote Similarity	NPC472115
0.6779	Remote Similarity	NPC39818
0.677	Remote Similarity	NPC323798
0.6763	Remote Similarity	NPC292265
0.6757	Remote Similarity	NPC80150
0.6757	Remote Similarity	NPC27833
0.6753	Remote Similarity	NPC316746
0.6744	Remote Similarity	NPC223595
0.6744	Remote Similarity	NPC167724
0.6744	Remote Similarity	NPC224970
0.6743	Remote Similarity	NPC475607
0.6743	Remote Similarity	NPC471743
0.6735	Remote Similarity	NPC229353
0.673	Remote Similarity	NPC315051
0.6724	Remote Similarity	NPC293255
0.6724	Remote Similarity	NPC181138
0.6724	Remote Similarity	NPC298851
0.6724	Remote Similarity	NPC21752
0.6724	Remote Similarity	NPC210415
0.6724	Remote Similarity	NPC276993
0.6711	Remote Similarity	NPC314278
0.6703	Remote Similarity	NPC472293
0.6689	Remote Similarity	NPC317758
0.6686	Remote Similarity	NPC41717
0.6686	Remote Similarity	NPC475594
0.6685	Remote Similarity	NPC473815
0.6667	Remote Similarity	NPC144691
0.6667	Remote Similarity	NPC474815
0.6667	Remote Similarity	NPC136002
0.6667	Remote Similarity	NPC475761
0.6667	Remote Similarity	NPC99043
0.6667	Remote Similarity	NPC218594
0.6647	Remote Similarity	NPC470971
0.6646	Remote Similarity	NPC254798
0.6645	Remote Similarity	NPC474926
0.6644	Remote Similarity	NPC190663
0.6644	Remote Similarity	NPC279385
0.6644	Remote Similarity	NPC179605
0.663	Remote Similarity	NPC472292
0.6628	Remote Similarity	NPC471130
0.6627	Remote Similarity	NPC104345
0.6619	Remote Similarity	NPC202613
0.6611	Remote Similarity	NPC97584
0.6609	Remote Similarity	NPC472118
0.6608	Remote Similarity	NPC293458
0.6607	Remote Similarity	NPC161827
0.66	Remote Similarity	NPC103292
0.6596	Remote Similarity	NPC472297
0.6596	Remote Similarity	NPC472296
0.6595	Remote Similarity	NPC472295
0.6595	Remote Similarity	NPC269886
0.6595	Remote Similarity	NPC81802
0.6595	Remote Similarity	NPC247735
0.6595	Remote Similarity	NPC472210
0.659	Remote Similarity	NPC278887
0.6588	Remote Similarity	NPC193410
0.6582	Remote Similarity	NPC300299
0.6582	Remote Similarity	NPC173295
0.6579	Remote Similarity	NPC192533
0.6573	Remote Similarity	NPC474041
0.6571	Remote Similarity	NPC355
0.6571	Remote Similarity	NPC474814
0.6571	Remote Similarity	NPC6982
0.6571	Remote Similarity	NPC112336
0.6562	Remote Similarity	NPC181527
0.6562	Remote Similarity	NPC83214
0.6556	Remote Similarity	NPC160493
0.6552	Remote Similarity	NPC474584
0.655	Remote Similarity	NPC322644
0.655	Remote Similarity	NPC248117
0.655	Remote Similarity	NPC201424
0.6533	Remote Similarity	NPC478014
0.6533	Remote Similarity	NPC478016
0.6533	Remote Similarity	NPC478015
0.6529	Remote Similarity	NPC61013
0.6529	Remote Similarity	NPC123241
0.6527	Remote Similarity	NPC154602
0.6524	Remote Similarity	NPC472116
0.6522	Remote Similarity	NPC471195
0.6522	Remote Similarity	NPC471196
0.6522	Remote Similarity	NPC12730
0.6519	Remote Similarity	NPC285923
0.6517	Remote Similarity	NPC315631
0.6512	Remote Similarity	NPC88970
0.651	Remote Similarity	NPC310467
0.6508	Remote Similarity	NPC317727
0.6503	Remote Similarity	NPC472323
0.65	Remote Similarity	NPC475962
0.65	Remote Similarity	NPC471317
0.6497	Remote Similarity	NPC469726
0.6497	Remote Similarity	NPC329338
0.6497	Remote Similarity	NPC470548
0.6497	Remote Similarity	NPC53044
0.6489	Remote Similarity	NPC472541
0.6489	Remote Similarity	NPC472542
0.6488	Remote Similarity	NPC285381
0.6481	Remote Similarity	NPC471164
0.648	Remote Similarity	NPC6974
0.6474	Remote Similarity	NPC313757
0.6474	Remote Similarity	NPC138293
0.6474	Remote Similarity	NPC113056
0.6471	Remote Similarity	NPC63370
0.6471	Remote Similarity	NPC36836
0.6467	Remote Similarity	NPC183805
0.6464	Remote Similarity	NPC243058
0.6464	Remote Similarity	NPC159125
0.6463	Remote Similarity	NPC130797
0.6461	Remote Similarity	NPC264482
0.6461	Remote Similarity	NPC203202
0.646	Remote Similarity	NPC153007
0.6453	Remote Similarity	NPC315368
0.6452	Remote Similarity	NPC476950
0.6443	Remote Similarity	NPC169328
0.6441	Remote Similarity	NPC477976
0.6436	Remote Similarity	NPC472540
0.6436	Remote Similarity	NPC472539
0.6436	Remote Similarity	NPC470787
0.6432	Remote Similarity	NPC147983
0.6432	Remote Similarity	NPC177996
0.6429	Remote Similarity	NPC203635
0.6429	Remote Similarity	NPC207851
0.6425	Remote Similarity	NPC186669
0.6424	Remote Similarity	NPC130931

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 NPC478039 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	134
0.1-0.2	422
0.2-0.3	846
0.3-0.4	1435
0.4-0.5	3408
0.5-0.6	2389
0.6-0.7	495
0.7-0.8	21
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
0.7818	Intermediate Similarity	NPD4092	Approved
0.7758	Intermediate Similarity	NPD4091	Approved
0.7697	Intermediate Similarity	NPD3522	Approved
0.7665	Intermediate Similarity	NPD3998	Approved
0.7665	Intermediate Similarity	NPD3999	Approved
0.7665	Intermediate Similarity	NPD3997	Approved
0.7605	Intermediate Similarity	NPD3991	Approved
0.7605	Intermediate Similarity	NPD3995	Approved
0.7605	Intermediate Similarity	NPD3994	Approved
0.7605	Intermediate Similarity	NPD3996	Approved
0.7605	Intermediate Similarity	NPD3992	Approved
0.7605	Intermediate Similarity	NPD3993	Approved
0.7574	Intermediate Similarity	NPD3990	Phase 3
0.7566	Intermediate Similarity	NPD3434	Clinical (unspecified phase)
0.7515	Intermediate Similarity	NPD3989	Phase 3
0.7484	Intermediate Similarity	NPD6017	Discontinued
0.7468	Intermediate Similarity	NPD2820	Phase 3
0.7403	Intermediate Similarity	NPD2365	Approved
0.7368	Intermediate Similarity	NPD2670	Approved
0.7355	Intermediate Similarity	NPD4464	Clinical (unspecified phase)
0.7297	Intermediate Similarity	NPD1781	Discontinued
0.7267	Intermediate Similarity	NPD2360	Approved
0.7219	Intermediate Similarity	NPD1527	Phase 2
0.7208	Intermediate Similarity	NPD6655	Clinical (unspecified phase)
0.72	Intermediate Similarity	NPD1069	Approved
0.72	Intermediate Similarity	NPD1070	Approved
0.7188	Intermediate Similarity	NPD5748	Phase 2
0.7182	Intermediate Similarity	NPD5856	Discontinued
0.7172	Intermediate Similarity	NPD1079	Discontinued
0.7162	Intermediate Similarity	NPD9540	Approved
0.7143	Intermediate Similarity	NPD181	Approved
0.7135	Intermediate Similarity	NPD5871	Discontinued
0.7134	Intermediate Similarity	NPD212	Discontinued
0.711	Intermediate Similarity	NPD5445	Approved
0.7101	Intermediate Similarity	NPD1575	Approved
0.7101	Intermediate Similarity	NPD1573	Approved
0.7076	Intermediate Similarity	NPD5466	Approved
0.7075	Intermediate Similarity	NPD1360	Approved
0.7063	Intermediate Similarity	NPD1802	Approved
0.7063	Intermediate Similarity	NPD1801	Approved
0.7059	Intermediate Similarity	NPD5727	Clinical (unspecified phase)
0.7048	Intermediate Similarity	NPD2506	Approved
0.7037	Intermediate Similarity	NPD5982	Phase 2
0.7027	Intermediate Similarity	NPD9541	Approved
0.7027	Intermediate Similarity	NPD9539	Approved
0.702	Intermediate Similarity	NPD2919	Clinical (unspecified phase)
0.702	Intermediate Similarity	NPD2918	Clinical (unspecified phase)
0.7013	Intermediate Similarity	NPD2470	Clinical (unspecified phase)
0.7006	Intermediate Similarity	NPD4461	Discontinued
0.6994	Remote Similarity	NPD3965	Phase 1
0.6987	Remote Similarity	NPD3170	Approved
0.6974	Remote Similarity	NPD1619	Phase 3
0.6964	Remote Similarity	NPD1631	Approved
0.6959	Remote Similarity	NPD1165	Clinical (unspecified phase)
0.6954	Remote Similarity	NPD663	Approved
0.6954	Remote Similarity	NPD662	Approved
0.6954	Remote Similarity	NPD658	Approved
0.6954	Remote Similarity	NPD659	Approved
0.6954	Remote Similarity	NPD656	Approved
0.6946	Remote Similarity	NPD7600	Phase 2
0.6919	Remote Similarity	NPD3377	Discontinued
0.6914	Remote Similarity	NPD7528	Approved
0.6914	Remote Similarity	NPD4432	Discontinued
0.6914	Remote Similarity	NPD4161	Discontinued
0.6908	Remote Similarity	NPD6359	Clinical (unspecified phase)
0.6903	Remote Similarity	NPD1410	Phase 1
0.6903	Remote Similarity	NPD2331	Discontinued
0.6901	Remote Similarity	NPD3376	Clinical (unspecified phase)
0.6887	Remote Similarity	NPD701	Approved
0.6887	Remote Similarity	NPD698	Approved
0.6886	Remote Similarity	NPD2427	Approved
0.6882	Remote Similarity	NPD4643	Clinical (unspecified phase)
0.6879	Remote Similarity	NPD12	Approved
0.6879	Remote Similarity	NPD1109	Approved
0.6879	Remote Similarity	NPD697	Approved
0.6879	Remote Similarity	NPD13	Approved
0.6879	Remote Similarity	NPD700	Approved
0.6879	Remote Similarity	NPD699	Approved
0.6879	Remote Similarity	NPD1110	Approved
0.6875	Remote Similarity	NPD5918	Discontinued
0.6871	Remote Similarity	NPD9272	Approved
0.6867	Remote Similarity	NPD7105	Phase 1
0.6857	Remote Similarity	NPD3782	Discontinued
0.6853	Remote Similarity	NPD23	Approved
0.6842	Remote Similarity	NPD2037	Approved
0.6824	Remote Similarity	NPD9692	Approved
0.6824	Remote Similarity	NPD1123	Approved
0.6824	Remote Similarity	NPD9693	Approved
0.6824	Remote Similarity	NPD1124	Approved
0.6818	Remote Similarity	NPD4329	Approved
0.6818	Remote Similarity	NPD7014	Clinical (unspecified phase)
0.6818	Remote Similarity	NPD4330	Approved
0.6815	Remote Similarity	NPD4077	Clinical (unspecified phase)
0.681	Remote Similarity	NPD4888	Discontinued
0.681	Remote Similarity	NPD979	Approved
0.6805	Remote Similarity	NPD4564	Clinical (unspecified phase)
0.6805	Remote Similarity	NPD4565	Clinical (unspecified phase)
0.6802	Remote Similarity	NPD7795	Phase 2
0.6798	Remote Similarity	NPD4412	Phase 2
0.6795	Remote Similarity	NPD1071	Clinical (unspecified phase)
0.6786	Remote Similarity	NPD7599	Phase 2
0.6786	Remote Similarity	NPD1630	Approved
0.6782	Remote Similarity	NPD4736	Clinical (unspecified phase)
0.6782	Remote Similarity	NPD3422	Phase 3
0.6782	Remote Similarity	NPD3423	Phase 2
0.6774	Remote Similarity	NPD6740	Clinical (unspecified phase)
0.6763	Remote Similarity	NPD2432	Approved
0.6763	Remote Similarity	NPD2431	Approved
0.676	Remote Similarity	NPD6163	Clinical (unspecified phase)
0.6755	Remote Similarity	NPD6325	Discontinued
0.6753	Remote Similarity	NPD486	Clinical (unspecified phase)
0.6752	Remote Similarity	NPD5227	Clinical (unspecified phase)
0.675	Remote Similarity	NPD6768	Approved
0.675	Remote Similarity	NPD6566	Discontinued
0.6747	Remote Similarity	NPD5086	Approved
0.6746	Remote Similarity	NPD4311	Approved
0.6744	Remote Similarity	NPD2455	Approved
0.6744	Remote Similarity	NPD2454	Approved
0.673	Remote Similarity	NPD989	Approved
0.6728	Remote Similarity	NPD2887	Clinical (unspecified phase)
0.6725	Remote Similarity	NPD5430	Discontinued
0.6721	Remote Similarity	NPD7570	Approved
0.6721	Remote Similarity	NPD7569	Approved
0.6709	Remote Similarity	NPD6342	Discontinued
0.6708	Remote Similarity	NPD5020	Approved
0.6708	Remote Similarity	NPD5024	Approved
0.6708	Remote Similarity	NPD7082	Approved
0.6705	Remote Similarity	NPD3792	Approved
0.669	Remote Similarity	NPD5631	Phase 3
0.6689	Remote Similarity	NPD1640	Clinical (unspecified phase)
0.6687	Remote Similarity	NPD3625	Discontinued
0.6686	Remote Similarity	NPD7449	Clinical (unspecified phase)
0.6685	Remote Similarity	NPD7429	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD4158	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD1541	Approved
0.6667	Remote Similarity	NPD5088	Discontinued
0.6667	Remote Similarity	NPD7142	Discontinued
0.6667	Remote Similarity	NPD3016	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD7259	Approved
0.6667	Remote Similarity	NPD5504	Discontinued
0.6667	Remote Similarity	NPD2336	Approved
0.6667	Remote Similarity	NPD951	Approved
0.6667	Remote Similarity	NPD5993	Phase 1
0.6667	Remote Similarity	NPD1663	Discontinued
0.6648	Remote Similarity	NPD2083	Clinical (unspecified phase)
0.6647	Remote Similarity	NPD2404	Discontinued
0.6646	Remote Similarity	NPD7478	Approved
0.6646	Remote Similarity	NPD6631	Clinical (unspecified phase)
0.6646	Remote Similarity	NPD7088	Discontinued
0.6645	Remote Similarity	NPD1036	Approved
0.6645	Remote Similarity	NPD6919	Clinical (unspecified phase)
0.6632	Remote Similarity	NPD3968	Approved
0.663	Remote Similarity	NPD3315	Phase 3
0.6628	Remote Similarity	NPD7591	Clinical (unspecified phase)
0.6627	Remote Similarity	NPD5715	Clinical (unspecified phase)
0.6627	Remote Similarity	NPD4517	Clinical (unspecified phase)
0.6626	Remote Similarity	NPD7295	Approved
0.6626	Remote Similarity	NPD5931	Phase 3
0.6626	Remote Similarity	NPD5932	Phase 3
0.6626	Remote Similarity	NPD5933	Phase 3
0.6624	Remote Similarity	NPD5182	Approved
0.6624	Remote Similarity	NPD5185	Approved
0.6624	Remote Similarity	NPD5184	Approved
0.6623	Remote Similarity	NPD4549	Discontinued
0.6623	Remote Similarity	NPD766	Clinical (unspecified phase)
0.6621	Remote Similarity	NPD1681	Approved
0.6621	Remote Similarity	NPD1682	Approved
0.6621	Remote Similarity	NPD1680	Approved
0.661	Remote Similarity	NPD8006	Clinical (unspecified phase)
0.6609	Remote Similarity	NPD2369	Discontinued
0.6606	Remote Similarity	NPD1664	Clinical (unspecified phase)
0.6606	Remote Similarity	NPD4682	Phase 2
0.6605	Remote Similarity	NPD1625	Approved
0.6604	Remote Similarity	NPD4214	Discontinued
0.6596	Remote Similarity	NPD6874	Approved
0.6593	Remote Similarity	NPD6891	Phase 2
0.6592	Remote Similarity	NPD3470	Approved
0.6592	Remote Similarity	NPD3471	Approved
0.6591	Remote Similarity	NPD5919	Clinical (unspecified phase)
0.659	Remote Similarity	NPD3587	Clinical (unspecified phase)
0.6588	Remote Similarity	NPD4335	Clinical (unspecified phase)
0.6584	Remote Similarity	NPD2010	Phase 3
0.6581	Remote Similarity	NPD1271	Clinical (unspecified phase)
0.6579	Remote Similarity	NPD660	Approved
0.6579	Remote Similarity	NPD657	Approved
0.6579	Remote Similarity	NPD661	Approved
0.6579	Remote Similarity	NPD655	Approved
0.6576	Remote Similarity	NPD5076	Approved
0.6576	Remote Similarity	NPD6659	Phase 2
0.6576	Remote Similarity	NPD5077	Approved
0.6573	Remote Similarity	NPD2869	Clinical (unspecified phase)
0.6573	Remote Similarity	NPD1587	Approved
0.6571	Remote Similarity	NPD3776	Discontinued
0.6568	Remote Similarity	NPD6913	Approved
0.6568	Remote Similarity	NPD6855	Clinical (unspecified phase)
0.6566	Remote Similarity	NPD2737	Clinical (unspecified phase)
0.6562	Remote Similarity	NPD4167	Phase 3
0.6561	Remote Similarity	NPD1874	Clinical (unspecified phase)
0.6561	Remote Similarity	NPD3137	Clinical (unspecified phase)
0.6561	Remote Similarity	NPD941	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