NPASS Compound

Structure

NPC473224 OpenBabel07101719242D 26 27 0 0 1 0 0 0 0 0999 V2000 -3.3668 -3.3003 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0678 -1.4254 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5867 -2.7335 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7058 -3.1257 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1345 -0.3813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9256 -2.5589 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2994 -0.8635 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1345 0.5829 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4643 -0.3813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2994 1.0651 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0447 -2.9512 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4643 0.5829 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.7354 -2.3844 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 0.6346 -1.4254 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.6292 1.0651 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.2005 -0.9432 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9590 1.0651 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3512 -0.7801 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.9590 0.1008 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 1.6163 -2.7766 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.6292 2.0294 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.0814 -1.3354 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7941 1.5472 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.1239 1.5472 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.2683 -0.4821 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 3 1 0 0 0 0 2 18 1 0 0 0 0 3 4 1 0 0 0 0 4 6 1 0 0 0 0 5 7 1 0 0 0 0 5 8 1 0 0 0 0 6 11 1 0 0 0 0 7 9 2 0 0 0 0 8 10 1 0 0 0 0 9 12 1 0 0 0 0 10 12 1 0 0 0 0 11 13 1 0 0 0 0 12 15 1 1 0 0 0 13 14 1 0 0 0 0 13 21 1 0 0 0 0 14 16 1 0 0 0 0 14 18 1 1 0 0 0 15 19 1 0 0 0 0 15 22 1 1 0 0 0 16 20 2 0 0 0 0 16 23 1 0 0 0 0 17 24 2 0 0 0 0 17 25 1 0 0 0 0 18 19 1 6 0 0 0 18 26 1 0 0 0 0 19 17 1 1 0 0 0 19 20 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	369.22
Volume:	375.896
LogP:	2.428
LogD:	1.71
LogS:	-2.614
# Rotatable Bonds:	8
TPSA:	127.09
# H-Bond Aceptor:	7
# H-Bond Donor:	5
# Rings:	2
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.32
Synthetic Accessibility Score:	4.736
Fsp3:	0.789
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
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:	-5.525
MDCK Permeability:	6.544931238749996e-05
Pgp-inhibitor:	0.001
Pgp-substrate:	0.086
Human Intestinal Absorption (HIA):	0.905
20% Bioavailability (F20%):	0.008
30% Bioavailability (F30%):	0.172

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.476
Plasma Protein Binding (PPB):	85.61034393310547%
Volume Distribution (VD):	0.454
Pgp-substrate:	20.645709991455078%

ADMET: Metabolism

CYP1A2-inhibitor:	0.014
CYP1A2-substrate:	0.541
CYP2C19-inhibitor:	0.026
CYP2C19-substrate:	0.54
CYP2C9-inhibitor:	0.054
CYP2C9-substrate:	0.858
CYP2D6-inhibitor:	0.005
CYP2D6-substrate:	0.091
CYP3A4-inhibitor:	0.029
CYP3A4-substrate:	0.05

ADMET: Excretion

Clearance (CL):	2.743
Half-life (T1/2):	0.762

ADMET: Toxicity

hERG Blockers:	0.014
Human Hepatotoxicity (H-HT):	0.096
Drug-inuced Liver Injury (DILI):	0.027
AMES Toxicity:	0.009
Rat Oral Acute Toxicity:	0.062
Maximum Recommended Daily Dose:	0.043
Skin Sensitization:	0.258
Carcinogencity:	0.312
Eye Corrosion:	0.006
Eye Irritation:	0.035
Respiratory Toxicity:	0.174

Download Data

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

Natural Product: NPC473224

Natural Product ID:	NPC473224
*Common Name:**	Cinnabaramide D
IUPAC Name:	(2R,3S,4R)-2-[(S)-[(1S)-cyclohex-2-en-1-yl]-hydroxymethyl]-3-hydroxy-4-(1-hydroxyhexyl)-3-methyl-5-oxopyrrolidine-2-carboxylic acid
Synonyms:	Cinnabaramide D
Standard InCHIKey:	HZMVPYGKRJDSSJ-MOEJHERCSA-N
Standard InCHI:	InChI=1S/C19H31NO6/c1-3-4-6-11-13(21)14-16(23)20-19(17(24)25,18(14,2)26)15(22)12-9-7-5-8-10-12/h7,9,12-15,21-22,26H,3-6,8,10-11H2,1-2H3,(H,20,23)(H,24,25)/t12-,13?,14+,15+,18+,19+/m1/s1
SMILES:	CCCCCC([C@H]1C(=N[C@]([C@@]1(C)O)(C(=O)O)[C@H]([C@H]1CCCC=C1)O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL374495
PubChem CID:	16109812
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

*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
NPO32890	terrestrial streptomycete	Species	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[17249727]

☑ 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
PROTEIN COMPLEX	19

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT24354	PROTEIN COMPLEX	20S proteasome	Homo sapiens	IC50	=	100.0	nM	PMID[470933]

☑ 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 NPC473224 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	86
0.1-0.2	525
0.2-0.3	4364
0.3-0.4	20133
0.4-0.5	11012
0.5-0.6	6244
0.6-0.7	307
0.7-0.8	15
0.8-0.85	5
0.85-0.9	2
0.9-0.95	2
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9891	High Similarity	NPC234542
0.9485	High Similarity	NPC473252
0.9381	High Similarity	NPC14537
0.866	High Similarity	NPC123141
0.8654	High Similarity	NPC12270
0.8585	High Similarity	NPC50694
0.8426	Intermediate Similarity	NPC201968
0.7593	Intermediate Similarity	NPC475800
0.7525	Intermediate Similarity	NPC314500
0.7455	Intermediate Similarity	NPC474725
0.7339	Intermediate Similarity	NPC472615
0.7248	Intermediate Similarity	NPC472616
0.7207	Intermediate Similarity	NPC70235
0.7115	Intermediate Similarity	NPC226513
0.7054	Intermediate Similarity	NPC307903
0.7054	Intermediate Similarity	NPC140251
0.703	Intermediate Similarity	NPC475753
0.7	Intermediate Similarity	NPC474563
0.7	Intermediate Similarity	NPC215988
0.6991	Remote Similarity	NPC133729
0.699	Remote Similarity	NPC118193
0.699	Remote Similarity	NPC256902
0.6875	Remote Similarity	NPC271269
0.6863	Remote Similarity	NPC258824
0.6842	Remote Similarity	NPC473578
0.6814	Remote Similarity	NPC251330
0.6796	Remote Similarity	NPC86005
0.6783	Remote Similarity	NPC476290
0.6759	Remote Similarity	NPC180722
0.6759	Remote Similarity	NPC165332
0.6759	Remote Similarity	NPC195645
0.6754	Remote Similarity	NPC475150
0.6729	Remote Similarity	NPC5418
0.6726	Remote Similarity	NPC154601
0.6701	Remote Similarity	NPC469514
0.6697	Remote Similarity	NPC475438
0.6667	Remote Similarity	NPC316250
0.6667	Remote Similarity	NPC469865
0.6667	Remote Similarity	NPC476269
0.6667	Remote Similarity	NPC39290
0.6667	Remote Similarity	NPC159369
0.6667	Remote Similarity	NPC97577
0.6638	Remote Similarity	NPC46764
0.6637	Remote Similarity	NPC74035
0.6635	Remote Similarity	NPC477959
0.6634	Remote Similarity	NPC474312
0.6633	Remote Similarity	NPC281296
0.6633	Remote Similarity	NPC240170
0.6633	Remote Similarity	NPC120776
0.6612	Remote Similarity	NPC323532
0.6583	Remote Similarity	NPC147707
0.6574	Remote Similarity	NPC473314
0.6571	Remote Similarity	NPC193386
0.6566	Remote Similarity	NPC121200
0.6555	Remote Similarity	NPC471645
0.6542	Remote Similarity	NPC36491
0.6542	Remote Similarity	NPC319473
0.6525	Remote Similarity	NPC1111
0.6525	Remote Similarity	NPC7797
0.6525	Remote Similarity	NPC261750
0.6508	Remote Similarity	NPC204556
0.65	Remote Similarity	NPC113363
0.6496	Remote Similarity	NPC113012
0.6496	Remote Similarity	NPC122926
0.6476	Remote Similarity	NPC472614
0.6471	Remote Similarity	NPC7414
0.646	Remote Similarity	NPC72401
0.646	Remote Similarity	NPC325339
0.6455	Remote Similarity	NPC477853
0.6449	Remote Similarity	NPC313670
0.6446	Remote Similarity	NPC188010
0.6446	Remote Similarity	NPC476190
0.6446	Remote Similarity	NPC316325
0.6436	Remote Similarity	NPC103634
0.6435	Remote Similarity	NPC475918
0.6429	Remote Similarity	NPC199445
0.6429	Remote Similarity	NPC60718
0.6422	Remote Similarity	NPC477290
0.6417	Remote Similarity	NPC476813
0.6417	Remote Similarity	NPC476814
0.641	Remote Similarity	NPC329305
0.6408	Remote Similarity	NPC69469
0.64	Remote Similarity	NPC218817
0.64	Remote Similarity	NPC11796
0.6396	Remote Similarity	NPC167380
0.6396	Remote Similarity	NPC4834
0.6393	Remote Similarity	NPC471118
0.6393	Remote Similarity	NPC471121
0.6393	Remote Similarity	NPC9714
0.6392	Remote Similarity	NPC167145
0.6392	Remote Similarity	NPC326024
0.6387	Remote Similarity	NPC60432
0.6381	Remote Similarity	NPC476982
0.6379	Remote Similarity	NPC315531
0.6373	Remote Similarity	NPC172309
0.6373	Remote Similarity	NPC14044
0.6373	Remote Similarity	NPC47031
0.6373	Remote Similarity	NPC88735
0.6373	Remote Similarity	NPC117960
0.6372	Remote Similarity	NPC474873
0.6371	Remote Similarity	NPC23963
0.6371	Remote Similarity	NPC469515
0.6364	Remote Similarity	NPC30196
0.6364	Remote Similarity	NPC54905
0.6364	Remote Similarity	NPC314009
0.6364	Remote Similarity	NPC279537
0.6356	Remote Similarity	NPC127578
0.6349	Remote Similarity	NPC469494
0.6346	Remote Similarity	NPC295799
0.6346	Remote Similarity	NPC477199
0.6339	Remote Similarity	NPC132931
0.6339	Remote Similarity	NPC477854
0.6337	Remote Similarity	NPC164308
0.6337	Remote Similarity	NPC308545
0.6337	Remote Similarity	NPC82488
0.6328	Remote Similarity	NPC329919
0.6328	Remote Similarity	NPC477793
0.6327	Remote Similarity	NPC330016
0.6321	Remote Similarity	NPC298904
0.632	Remote Similarity	NPC478014
0.632	Remote Similarity	NPC478015
0.632	Remote Similarity	NPC478016
0.6316	Remote Similarity	NPC469598
0.6316	Remote Similarity	NPC474747
0.6311	Remote Similarity	NPC47135
0.6311	Remote Similarity	NPC471120
0.6311	Remote Similarity	NPC216335
0.6311	Remote Similarity	NPC474252
0.6311	Remote Similarity	NPC6531
0.6311	Remote Similarity	NPC471117
0.6306	Remote Similarity	NPC469528
0.6306	Remote Similarity	NPC473859
0.6306	Remote Similarity	NPC475503
0.6306	Remote Similarity	NPC121857
0.6306	Remote Similarity	NPC469369
0.63	Remote Similarity	NPC145898
0.63	Remote Similarity	NPC316242
0.6296	Remote Similarity	NPC473448
0.6289	Remote Similarity	NPC126061
0.6286	Remote Similarity	NPC475206
0.6275	Remote Similarity	NPC115418
0.6273	Remote Similarity	NPC470958
0.6273	Remote Similarity	NPC470957
0.6271	Remote Similarity	NPC474891
0.6262	Remote Similarity	NPC34754
0.6262	Remote Similarity	NPC202672
0.6261	Remote Similarity	NPC4620
0.6261	Remote Similarity	NPC475945
0.6261	Remote Similarity	NPC475871
0.626	Remote Similarity	NPC314361
0.626	Remote Similarity	NPC476952
0.625	Remote Similarity	NPC40812
0.625	Remote Similarity	NPC199557
0.625	Remote Similarity	NPC476983
0.625	Remote Similarity	NPC11620
0.625	Remote Similarity	NPC66108
0.6239	Remote Similarity	NPC300312
0.6239	Remote Similarity	NPC261607
0.6239	Remote Similarity	NPC111114
0.6239	Remote Similarity	NPC184463
0.6238	Remote Similarity	NPC315535
0.6238	Remote Similarity	NPC192006
0.6238	Remote Similarity	NPC478017
0.6238	Remote Similarity	NPC253703
0.6238	Remote Similarity	NPC315131
0.6238	Remote Similarity	NPC314858
0.6238	Remote Similarity	NPC200085
0.6238	Remote Similarity	NPC127526
0.6238	Remote Similarity	NPC51695
0.6228	Remote Similarity	NPC474742
0.6228	Remote Similarity	NPC472753
0.6226	Remote Similarity	NPC477994
0.6226	Remote Similarity	NPC116575
0.6226	Remote Similarity	NPC262085
0.6226	Remote Similarity	NPC477993
0.6218	Remote Similarity	NPC477997
0.6218	Remote Similarity	NPC92829
0.6216	Remote Similarity	NPC266899
0.6216	Remote Similarity	NPC475659
0.6214	Remote Similarity	NPC191711
0.6207	Remote Similarity	NPC475036
0.6207	Remote Similarity	NPC259476
0.6207	Remote Similarity	NPC220964
0.6207	Remote Similarity	NPC201763
0.6207	Remote Similarity	NPC475676
0.6207	Remote Similarity	NPC119329
0.6204	Remote Similarity	NPC295312
0.6204	Remote Similarity	NPC52198
0.6204	Remote Similarity	NPC117405
0.6202	Remote Similarity	NPC476957
0.62	Remote Similarity	NPC474447
0.6198	Remote Similarity	NPC106479
0.6195	Remote Similarity	NPC308567
0.6195	Remote Similarity	NPC83895
0.6195	Remote Similarity	NPC255592
0.6195	Remote Similarity	NPC187761
0.6195	Remote Similarity	NPC114274
0.6195	Remote Similarity	NPC261377
0.619	Remote Similarity	NPC474776
0.619	Remote Similarity	NPC80150

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 NPC473224 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	97
0.1-0.2	568
0.2-0.3	3650
0.3-0.4	3403
0.4-0.5	1120
0.5-0.6	275
0.6-0.7	35
0.7-0.8	1
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8654	High Similarity	NPD1719	Phase 1
0.7083	Intermediate Similarity	NPD3732	Approved
0.708	Intermediate Similarity	NPD6420	Discontinued
0.6792	Remote Similarity	NPD5781	Clinical (unspecified phase)
0.6792	Remote Similarity	NPD5778	Approved
0.6792	Remote Similarity	NPD5779	Approved
0.6783	Remote Similarity	NPD6421	Discontinued
0.6769	Remote Similarity	NPD6333	Approved
0.6769	Remote Similarity	NPD6334	Approved
0.6759	Remote Similarity	NPD7839	Suspended
0.67	Remote Similarity	NPD5369	Approved
0.6667	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6101	Approved
0.66	Remote Similarity	NPD5368	Approved
0.6542	Remote Similarity	NPD6411	Approved
0.6538	Remote Similarity	NPD5786	Approved
0.6508	Remote Similarity	NPD8074	Phase 3
0.6471	Remote Similarity	NPD6435	Approved
0.6471	Remote Similarity	NPD4270	Approved
0.6471	Remote Similarity	NPD4269	Approved
0.6455	Remote Similarity	NPD4228	Discovery
0.6446	Remote Similarity	NPD7500	Approved
0.6389	Remote Similarity	NPD7983	Approved
0.6311	Remote Similarity	NPD7345	Approved
0.6286	Remote Similarity	NPD5363	Approved
0.6275	Remote Similarity	NPD4819	Approved
0.6275	Remote Similarity	NPD4252	Approved
0.6275	Remote Similarity	NPD4821	Approved
0.6275	Remote Similarity	NPD4822	Approved
0.6275	Remote Similarity	NPD4820	Approved
0.6238	Remote Similarity	NPD7917	Clinical (unspecified phase)
0.6238	Remote Similarity	NPD7918	Clinical (unspecified phase)
0.6231	Remote Similarity	NPD6914	Discontinued
0.6179	Remote Similarity	NPD8137	Clinical (unspecified phase)
0.6167	Remote Similarity	NPD7116	Clinical (unspecified phase)
0.6154	Remote Similarity	NPD4211	Phase 1
0.6134	Remote Similarity	NPD6413	Approved
0.6095	Remote Similarity	NPD7154	Phase 3
0.6095	Remote Similarity	NPD5362	Discontinued
0.6094	Remote Similarity	NPD8342	Approved
0.6094	Remote Similarity	NPD8340	Approved
0.6094	Remote Similarity	NPD8341	Approved
0.6094	Remote Similarity	NPD8299	Approved
0.6078	Remote Similarity	NPD4271	Approved
0.6078	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6078	Remote Similarity	NPD4268	Approved
0.6071	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6047	Remote Similarity	NPD8451	Approved
0.6016	Remote Similarity	NPD7642	Approved
0.6	Remote Similarity	NPD5785	Approved
0.6	Remote Similarity	NPD6404	Discontinued
0.6	Remote Similarity	NPD8448	Approved
0.6	Remote Similarity	NPD7641	Discontinued
0.5985	Remote Similarity	NPD8390	Approved
0.5985	Remote Similarity	NPD8392	Approved
0.5985	Remote Similarity	NPD8391	Approved
0.5984	Remote Similarity	NPD8444	Approved
0.5984	Remote Similarity	NPD8274	Clinical (unspecified phase)
0.5982	Remote Similarity	NPD5282	Discontinued
0.5962	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.5946	Remote Similarity	NPD7637	Suspended
0.5938	Remote Similarity	NPD8080	Discontinued
0.5926	Remote Similarity	NPD4249	Approved
0.5905	Remote Similarity	NPD1448	Clinical (unspecified phase)
0.5902	Remote Similarity	NPD2204	Approved
0.5891	Remote Similarity	NPD7829	Approved
0.5891	Remote Similarity	NPD7830	Approved
0.5872	Remote Similarity	NPD4251	Approved
0.5872	Remote Similarity	NPD4250	Approved
0.5856	Remote Similarity	NPD6698	Approved
0.5856	Remote Similarity	NPD46	Approved
0.5833	Remote Similarity	NPD467	Phase 1
0.5818	Remote Similarity	NPD4264	Clinical (unspecified phase)
0.5806	Remote Similarity	NPD1376	Discontinued
0.5802	Remote Similarity	NPD8273	Phase 1
0.5794	Remote Similarity	NPD5332	Approved
0.5794	Remote Similarity	NPD7505	Discontinued
0.5794	Remote Similarity	NPD5331	Approved
0.5778	Remote Similarity	NPD2613	Approved
0.5773	Remote Similarity	NPD7331	Phase 2
0.5772	Remote Similarity	NPD3642	Approved
0.5772	Remote Similarity	NPD7601	Clinical (unspecified phase)
0.5772	Remote Similarity	NPD3643	Approved
0.5772	Remote Similarity	NPD3644	Approved
0.5755	Remote Similarity	NPD4790	Discontinued
0.5755	Remote Similarity	NPD857	Phase 3
0.5739	Remote Similarity	NPD5349	Clinical (unspecified phase)
0.5736	Remote Similarity	NPD8513	Phase 3
0.5736	Remote Similarity	NPD6909	Approved
0.5736	Remote Similarity	NPD8515	Approved
0.5736	Remote Similarity	NPD8516	Approved
0.5736	Remote Similarity	NPD8517	Approved
0.5736	Remote Similarity	NPD6908	Approved
0.5736	Remote Similarity	NPD7739	Clinical (unspecified phase)
0.5735	Remote Similarity	NPD4738	Phase 2
0.5726	Remote Similarity	NPD6053	Discontinued
0.5714	Remote Similarity	NPD4247	Clinical (unspecified phase)
0.5702	Remote Similarity	NPD5697	Approved
0.5701	Remote Similarity	NPD3667	Approved
0.5693	Remote Similarity	NPD8415	Approved
0.5692	Remote Similarity	NPD7623	Phase 3
0.5692	Remote Similarity	NPD7624	Clinical (unspecified phase)
0.5691	Remote Similarity	NPD4634	Approved
0.5688	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.5688	Remote Similarity	NPD619	Phase 3
0.5664	Remote Similarity	NPD4810	Clinical (unspecified phase)
0.5659	Remote Similarity	NPD2218	Phase 2
0.5659	Remote Similarity	NPD2217	Approved
0.5659	Remote Similarity	NPD6319	Approved
0.5656	Remote Similarity	NPD6899	Approved
0.5656	Remote Similarity	NPD6881	Approved
0.5652	Remote Similarity	NPD3615	Approved
0.5652	Remote Similarity	NPD2574	Discontinued
0.5652	Remote Similarity	NPD2573	Approved
0.5652	Remote Similarity	NPD3614	Approved
0.5652	Remote Similarity	NPD3087	Approved
0.5652	Remote Similarity	NPD3088	Approved
0.5652	Remote Similarity	NPD4746	Phase 3
0.5652	Remote Similarity	NPD2571	Approved
0.5652	Remote Similarity	NPD2570	Approved
0.5652	Remote Similarity	NPD2566	Approved
0.5652	Remote Similarity	NPD3616	Approved
0.5652	Remote Similarity	NPD4745	Approved
0.5652	Remote Similarity	NPD2572	Clinical (unspecified phase)
0.5652	Remote Similarity	NPD3090	Approved
0.5652	Remote Similarity	NPD3089	Approved
0.5635	Remote Similarity	NPD2650	Approved
0.5635	Remote Similarity	NPD2652	Approved
0.5625	Remote Similarity	NPD5370	Suspended
0.562	Remote Similarity	NPD5357	Phase 1
0.562	Remote Similarity	NPD7128	Approved
0.562	Remote Similarity	NPD7333	Discontinued
0.562	Remote Similarity	NPD6402	Approved
0.562	Remote Similarity	NPD5739	Approved
0.562	Remote Similarity	NPD6675	Approved
0.5615	Remote Similarity	NPD5981	Approved
0.5614	Remote Similarity	NPD6399	Phase 3
0.561	Remote Similarity	NPD6014	Approved
0.561	Remote Similarity	NPD8306	Approved
0.561	Remote Similarity	NPD6013	Approved
0.561	Remote Similarity	NPD6012	Approved
0.561	Remote Similarity	NPD8305	Approved
0.5606	Remote Similarity	NPD4217	Approved
0.5606	Remote Similarity	NPD2611	Approved
0.5606	Remote Similarity	NPD3131	Approved
0.5606	Remote Similarity	NPD2610	Approved
0.5606	Remote Similarity	NPD4216	Approved
0.5606	Remote Similarity	NPD3132	Approved
0.5606	Remote Similarity	NPD2612	Approved
0.5606	Remote Similarity	NPD4218	Approved
0.5606	Remote Similarity	NPD2609	Approved
0.5606	Remote Similarity	NPD2608	Approved
0.5606	Remote Similarity	NPD4215	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