NPASS Compound

Structure

NPC50694 OpenBabel07101719252D 34 35 0 0 1 0 0 0 0 0999 V2000 -3.3945 -3.3275 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6508 3.9905 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0848 -1.4371 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6080 -2.7560 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7198 -3.1515 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9333 -2.5800 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1767 -0.3845 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3348 -0.8706 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1767 0.5877 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0451 -2.9754 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4928 -0.3845 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3348 1.0738 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7415 -2.4040 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1249 2.5322 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6508 3.0183 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4928 0.5877 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.6398 -1.4371 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.9669 3.0183 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.6508 1.0738 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.2021 -0.9510 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9669 3.9905 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9669 1.0738 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3623 -0.7865 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.9669 0.1016 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.8089 2.5322 0.0000 N 0 0 0 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 3.4928 2.5322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.6508 2.0461 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.0903 -1.3464 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.1249 4.4766 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.8089 4.4766 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.8089 1.5600 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.2870 -0.4861 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.1249 1.5600 0.0000 S 0 0 0 0 0 0 0 0 0 0 0 0 1 4 1 0 0 0 0 2 15 1 0 0 0 0 3 23 1 0 0 0 0 4 5 1 0 0 0 0 5 6 1 0 0 0 0 6 10 1 0 0 0 0 7 8 1 0 0 0 0 7 9 1 0 0 0 0 8 11 2 0 0 0 0 9 12 1 0 0 0 0 10 13 1 0 0 0 0 11 16 1 0 0 0 0 12 16 1 0 0 0 0 13 17 1 0 0 0 0 14 34 1 0 0 0 0 15 25 2 3 0 0 0 15 27 1 0 0 0 0 16 19 1 1 0 0 0 17 20 1 0 0 0 0 17 23 1 1 0 0 0 18 14 1 1 0 0 0 18 21 1 0 0 0 0 18 25 1 0 0 0 0 19 24 1 0 0 0 0 19 28 1 1 0 0 0 20 26 2 0 0 0 0 20 29 1 0 0 0 0 21 30 2 0 0 0 0 21 31 1 0 0 0 0 22 32 2 0 0 0 0 22 34 1 0 0 0 0 23 24 1 6 0 0 0 23 33 1 0 0 0 0 24 22 1 1 0 0 0 24 26 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	498.24
Volume:	495.399
LogP:	2.922
LogD:	1.808
LogS:	-2.904
# Rotatable Bonds:	14
TPSA:	153.03
# H-Bond Aceptor:	9
# H-Bond Donor:	5
# Rings:	2
# Heavy Atoms:	10

MedChem Properties

QED Drug-Likeness Score:	0.202
Synthetic Accessibility Score:	4.713
Fsp3:	0.75
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.752
MDCK Permeability:	2.970703917526407e-06
Pgp-inhibitor:	0.003
Pgp-substrate:	0.513
Human Intestinal Absorption (HIA):	0.962
20% Bioavailability (F20%):	0.028
30% Bioavailability (F30%):	0.876

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.201
Plasma Protein Binding (PPB):	88.5229263305664%
Volume Distribution (VD):	0.4
Pgp-substrate:	17.340444564819336%

ADMET: Metabolism

CYP1A2-inhibitor:	0.004
CYP1A2-substrate:	0.342
CYP2C19-inhibitor:	0.029
CYP2C19-substrate:	0.075
CYP2C9-inhibitor:	0.054
CYP2C9-substrate:	0.866
CYP2D6-inhibitor:	0.003
CYP2D6-substrate:	0.093
CYP3A4-inhibitor:	0.066
CYP3A4-substrate:	0.043

ADMET: Excretion

Clearance (CL):	2.569
Half-life (T1/2):	0.714

ADMET: Toxicity

hERG Blockers:	0.006
Human Hepatotoxicity (H-HT):	0.069
Drug-inuced Liver Injury (DILI):	0.048
AMES Toxicity:	0.013
Rat Oral Acute Toxicity:	0.008
Maximum Recommended Daily Dose:	0.016
Skin Sensitization:	0.399
Carcinogencity:	0.778
Eye Corrosion:	0.003
Eye Irritation:	0.033
Respiratory Toxicity:	0.145

Download Data

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

Natural Product: NPC50694

Natural Product ID:	NPC50694
*Common Name:**	Cinnabaramide F
IUPAC Name:	(2R)-2-acetamido-3-[(2R,3S,4R)-2-[(S)-[(1S)-cyclohex-2-en-1-yl]-hydroxymethyl]-4-hexyl-3-hydroxy-3-methyl-5-oxopyrrolidine-2-carbonyl]sulfanylpropanoic acid
Synonyms:	Cinnabaramide F
Standard InCHIKey:	LNANRAACAKDGBI-HIOGCZMJSA-N
Standard InCHI:	InChI=1S/C24H38N2O7S/c1-4-5-6-10-13-17-20(29)26-24(23(17,3)33,19(28)16-11-8-7-9-12-16)22(32)34-14-18(21(30)31)25-15(2)27/h8,11,16-19,28,33H,4-7,9-10,12-14H2,1-3H3,(H,25,27)(H,26,29)(H,30,31)/t16-,17+,18+,19+,23+,24+/m1/s1
SMILES:	CCCCCC[C@H]1C(=N[C@]([C@@]1(C)O)(C(=O)SC[C@@H](C(=O)O)N=C(O)C)[C@H]([C@H]1CCCC=C1)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL221585
PubChem CID:	16109813
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:0001189] N-acyl-alpha amino acids and derivatives [CHEMONTID:0002402] N-acyl-alpha amino acids [CHEMONTID:0004148] N-acyl-L-alpha-amino acids

*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
Others	1

Activity Type	# Activity
Others	1
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	=	6.0	nM	PMID[497431]
NPT35	Others	n.a.		Stability	>	90.0	%	PMID[497431]

☑ 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 NPC50694 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	66
0.1-0.2	589
0.2-0.3	7445
0.3-0.4	20782
0.4-0.5	11770
0.5-0.6	1905
0.6-0.7	114
0.7-0.8	15
0.8-0.85	3
0.85-0.9	4
0.9-0.95	1
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9813	High Similarity	NPC201968
0.8667	High Similarity	NPC234542
0.8585	High Similarity	NPC473224
0.8273	Intermediate Similarity	NPC14537
0.8198	Intermediate Similarity	NPC473252
0.781	Intermediate Similarity	NPC193386
0.7692	Intermediate Similarity	NPC12270
0.7636	Intermediate Similarity	NPC123141
0.7611	Intermediate Similarity	NPC325339
0.7611	Intermediate Similarity	NPC72401
0.7593	Intermediate Similarity	NPC319473
0.7521	Intermediate Similarity	NPC329305
0.75	Intermediate Similarity	NPC132931
0.7227	Intermediate Similarity	NPC474891
0.7217	Intermediate Similarity	NPC474873
0.7203	Intermediate Similarity	NPC475800
0.7167	Intermediate Similarity	NPC127578
0.7083	Intermediate Similarity	NPC474725
0.7049	Intermediate Similarity	NPC268327
0.7049	Intermediate Similarity	NPC273215
0.7049	Intermediate Similarity	NPC295444
0.7049	Intermediate Similarity	NPC279383
0.6975	Remote Similarity	NPC135216
0.6975	Remote Similarity	NPC101106
0.6875	Remote Similarity	NPC319021
0.686	Remote Similarity	NPC471636
0.686	Remote Similarity	NPC307903
0.686	Remote Similarity	NPC474969
0.686	Remote Similarity	NPC140251
0.686	Remote Similarity	NPC287572
0.686	Remote Similarity	NPC476034
0.6857	Remote Similarity	NPC160222
0.6857	Remote Similarity	NPC193753
0.6855	Remote Similarity	NPC475988
0.6807	Remote Similarity	NPC474563
0.6777	Remote Similarity	NPC250187
0.6694	Remote Similarity	NPC472615
0.6667	Remote Similarity	NPC473578
0.6614	Remote Similarity	NPC477554
0.6612	Remote Similarity	NPC472616
0.6612	Remote Similarity	NPC74035
0.6606	Remote Similarity	NPC474312
0.6585	Remote Similarity	NPC70235
0.6585	Remote Similarity	NPC475150
0.6562	Remote Similarity	NPC477553
0.6522	Remote Similarity	NPC314500
0.6512	Remote Similarity	NPC477555
0.6508	Remote Similarity	NPC469865
0.6491	Remote Similarity	NPC39290
0.6491	Remote Similarity	NPC159369
0.6423	Remote Similarity	NPC475918
0.6406	Remote Similarity	NPC471645
0.64	Remote Similarity	NPC133729
0.6393	Remote Similarity	NPC215988
0.6349	Remote Similarity	NPC476290
0.6349	Remote Similarity	NPC113012
0.6349	Remote Similarity	NPC122926
0.6325	Remote Similarity	NPC226513
0.6324	Remote Similarity	NPC329919
0.6324	Remote Similarity	NPC477793
0.6316	Remote Similarity	NPC478015
0.6316	Remote Similarity	NPC478014
0.6316	Remote Similarity	NPC478016
0.6304	Remote Similarity	NPC314686
0.6304	Remote Similarity	NPC268844
0.6296	Remote Similarity	NPC316242
0.629	Remote Similarity	NPC271269
0.6279	Remote Similarity	NPC476814
0.6279	Remote Similarity	NPC476813
0.625	Remote Similarity	NPC476269
0.625	Remote Similarity	NPC474995
0.625	Remote Similarity	NPC261750
0.625	Remote Similarity	NPC204556
0.625	Remote Similarity	NPC1111
0.624	Remote Similarity	NPC251330
0.6239	Remote Similarity	NPC315535
0.6239	Remote Similarity	NPC315131
0.6239	Remote Similarity	NPC478017
0.623	Remote Similarity	NPC316250
0.6228	Remote Similarity	NPC258824
0.6228	Remote Similarity	NPC475753
0.622	Remote Similarity	NPC46764
0.6212	Remote Similarity	NPC323532
0.6207	Remote Similarity	NPC256902
0.6207	Remote Similarity	NPC118193
0.6195	Remote Similarity	NPC477199
0.6183	Remote Similarity	NPC147707
0.6183	Remote Similarity	NPC188010
0.6167	Remote Similarity	NPC475503
0.616	Remote Similarity	NPC154601
0.6136	Remote Similarity	NPC9714
0.6136	Remote Similarity	NPC471118
0.6136	Remote Similarity	NPC471121
0.6124	Remote Similarity	NPC60432
0.6116	Remote Similarity	NPC4834
0.6111	Remote Similarity	NPC315531
0.6107	Remote Similarity	NPC30196
0.608	Remote Similarity	NPC119329
0.6074	Remote Similarity	NPC273185
0.6061	Remote Similarity	NPC6531
0.6061	Remote Similarity	NPC316325
0.6061	Remote Similarity	NPC471117
0.6061	Remote Similarity	NPC471120
0.6061	Remote Similarity	NPC476190
0.6055	Remote Similarity	NPC469514
0.6047	Remote Similarity	NPC476875
0.6047	Remote Similarity	NPC29501
0.6045	Remote Similarity	NPC310467
0.6034	Remote Similarity	NPC86005
0.6033	Remote Similarity	NPC165332
0.6033	Remote Similarity	NPC180722
0.6033	Remote Similarity	NPC195645
0.6031	Remote Similarity	NPC474984
0.6028	Remote Similarity	NPC314361
0.6018	Remote Similarity	NPC47135
0.6016	Remote Similarity	NPC233932
0.6015	Remote Similarity	NPC315974
0.6	Remote Similarity	NPC469515
0.6	Remote Similarity	NPC5418
0.6	Remote Similarity	NPC476877
0.6	Remote Similarity	NPC23963
0.6	Remote Similarity	NPC281296
0.5986	Remote Similarity	NPC76999
0.5985	Remote Similarity	NPC469494
0.5984	Remote Similarity	NPC475438
0.5984	Remote Similarity	NPC475646
0.5983	Remote Similarity	NPC34754
0.597	Remote Similarity	NPC169328
0.5969	Remote Similarity	NPC477997
0.5957	Remote Similarity	NPC139585
0.5956	Remote Similarity	NPC80150
0.5946	Remote Similarity	NPC121200
0.5944	Remote Similarity	NPC75318
0.594	Remote Similarity	NPC209734
0.5938	Remote Similarity	NPC207820
0.5932	Remote Similarity	NPC97577
0.592	Remote Similarity	NPC128501
0.592	Remote Similarity	NPC477198
0.5909	Remote Similarity	NPC470540
0.5906	Remote Similarity	NPC258130
0.5906	Remote Similarity	NPC476876
0.5903	Remote Similarity	NPC145899
0.5903	Remote Similarity	NPC472430
0.5897	Remote Similarity	NPC472614
0.5897	Remote Similarity	NPC477959
0.5882	Remote Similarity	NPC314293
0.5882	Remote Similarity	NPC315188
0.5878	Remote Similarity	NPC7797
0.5878	Remote Similarity	NPC475394
0.5878	Remote Similarity	NPC475152
0.5878	Remote Similarity	NPC475584
0.5877	Remote Similarity	NPC7414
0.587	Remote Similarity	NPC314512
0.587	Remote Similarity	NPC314451
0.587	Remote Similarity	NPC204639
0.587	Remote Similarity	NPC313333
0.587	Remote Similarity	NPC313342
0.5868	Remote Similarity	NPC477290
0.5868	Remote Similarity	NPC473314
0.5862	Remote Similarity	NPC230889
0.5857	Remote Similarity	NPC47667
0.5856	Remote Similarity	NPC120776
0.5856	Remote Similarity	NPC240170
0.5854	Remote Similarity	NPC167380
0.5852	Remote Similarity	NPC67917
0.5852	Remote Similarity	NPC313802
0.5852	Remote Similarity	NPC477515
0.5852	Remote Similarity	NPC314268
0.585	Remote Similarity	NPC210729
0.585	Remote Similarity	NPC82931
0.585	Remote Similarity	NPC172365
0.5847	Remote Similarity	NPC316186
0.5845	Remote Similarity	NPC475472
0.5841	Remote Similarity	NPC311369
0.584	Remote Similarity	NPC77703
0.5839	Remote Similarity	NPC190663
0.5839	Remote Similarity	NPC475892
0.5833	Remote Similarity	NPC469597
0.5833	Remote Similarity	NPC106479
0.5833	Remote Similarity	NPC36491
0.5826	Remote Similarity	NPC69469
0.5822	Remote Similarity	NPC200788
0.5822	Remote Similarity	NPC243680
0.582	Remote Similarity	NPC314009
0.582	Remote Similarity	NPC54905
0.5818	Remote Similarity	NPC199445
0.5816	Remote Similarity	NPC471471
0.5816	Remote Similarity	NPC121601
0.5816	Remote Similarity	NPC164476
0.5814	Remote Similarity	NPC171734
0.5814	Remote Similarity	NPC15413
0.5814	Remote Similarity	NPC476276
0.5812	Remote Similarity	NPC476982
0.5804	Remote Similarity	NPC474833
0.5804	Remote Similarity	NPC218817
0.5804	Remote Similarity	NPC473984
0.5804	Remote Similarity	NPC73829
0.5804	Remote Similarity	NPC11796
0.5804	Remote Similarity	NPC119794
0.5802	Remote Similarity	NPC21713

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 NPC50694 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	70
0.1-0.2	421
0.2-0.3	3442
0.3-0.4	3805
0.4-0.5	1153
0.5-0.6	246
0.6-0.7	11
0.7-0.8	2
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
0.7692	Intermediate Similarity	NPD1719	Phase 1
0.7018	Intermediate Similarity	NPD4228	Discovery
0.6975	Remote Similarity	NPD4211	Phase 1
0.6885	Remote Similarity	NPD6420	Discontinued
0.6803	Remote Similarity	NPD6413	Approved
0.6748	Remote Similarity	NPD6421	Discontinued
0.6609	Remote Similarity	NPD5781	Clinical (unspecified phase)
0.6389	Remote Similarity	NPD3732	Approved
0.6379	Remote Similarity	NPD4810	Clinical (unspecified phase)
0.6348	Remote Similarity	NPD5370	Suspended
0.6239	Remote Similarity	NPD7917	Clinical (unspecified phase)
0.6239	Remote Similarity	NPD7918	Clinical (unspecified phase)
0.6212	Remote Similarity	NPD7519	Approved
0.6212	Remote Similarity	NPD7518	Approved
0.6212	Remote Similarity	NPD7517	Approved
0.6138	Remote Similarity	NPD6865	Phase 2
0.6138	Remote Similarity	NPD6864	Phase 2
0.6115	Remote Similarity	NPD6914	Discontinued
0.6087	Remote Similarity	NPD6422	Discontinued
0.6071	Remote Similarity	NPD5369	Approved
0.6061	Remote Similarity	NPD7505	Discontinued
0.6061	Remote Similarity	NPD7500	Approved
0.605	Remote Similarity	NPD5778	Approved
0.605	Remote Similarity	NPD5779	Approved
0.6045	Remote Similarity	NPD7148	Clinical (unspecified phase)
0.6045	Remote Similarity	NPD7147	Phase 3
0.6042	Remote Similarity	NPD6334	Approved
0.6042	Remote Similarity	NPD6333	Approved
0.6033	Remote Similarity	NPD7839	Suspended
0.6018	Remote Similarity	NPD7345	Approved
0.6	Remote Similarity	NPD7751	Phase 1
0.6	Remote Similarity	NPD4209	Clinical (unspecified phase)
0.5966	Remote Similarity	NPD1749	Approved
0.594	Remote Similarity	NPD8137	Clinical (unspecified phase)
0.5932	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.5932	Remote Similarity	NPD6101	Approved
0.5926	Remote Similarity	NPD6093	Discontinued
0.5918	Remote Similarity	NPD6077	Discontinued
0.5915	Remote Similarity	NPD4125	Approved
0.5909	Remote Similarity	NPD7915	Approved
0.5909	Remote Similarity	NPD7916	Approved
0.5906	Remote Similarity	NPD2436	Approved
0.5906	Remote Similarity	NPD2437	Approved
0.5899	Remote Similarity	NPD8074	Phase 3
0.5897	Remote Similarity	NPD6915	Approved
0.5887	Remote Similarity	NPD8392	Approved
0.5887	Remote Similarity	NPD8390	Approved
0.5887	Remote Similarity	NPD8391	Approved
0.5882	Remote Similarity	NPD6095	Approved
0.5882	Remote Similarity	NPD6094	Approved
0.5877	Remote Similarity	NPD4269	Approved
0.5877	Remote Similarity	NPD4270	Approved
0.587	Remote Similarity	NPD8341	Approved
0.587	Remote Similarity	NPD8340	Approved
0.587	Remote Similarity	NPD8299	Approved
0.587	Remote Similarity	NPD8342	Approved
0.586	Remote Similarity	NPD7749	Clinical (unspecified phase)
0.5844	Remote Similarity	NPD6390	Discontinued
0.5841	Remote Similarity	NPD5368	Approved
0.5833	Remote Similarity	NPD6411	Approved
0.5827	Remote Similarity	NPD8451	Approved
0.5827	Remote Similarity	NPD8273	Phase 1
0.5827	Remote Similarity	NPD3677	Clinical (unspecified phase)
0.5812	Remote Similarity	NPD5786	Approved
0.5802	Remote Similarity	NPD7116	Clinical (unspecified phase)
0.5797	Remote Similarity	NPD7642	Approved
0.5786	Remote Similarity	NPD8448	Approved
0.5778	Remote Similarity	NPD7641	Discontinued
0.5766	Remote Similarity	NPD8444	Approved
0.5766	Remote Similarity	NPD8274	Clinical (unspecified phase)
0.5753	Remote Similarity	NPD5323	Approved
0.5739	Remote Similarity	NPD6435	Approved
0.5736	Remote Similarity	NPD2147	Approved
0.5735	Remote Similarity	NPD3159	Discontinued
0.5734	Remote Similarity	NPD7828	Discontinued
0.5726	Remote Similarity	NPD842	Phase 3
0.5726	Remote Similarity	NPD5363	Approved
0.5725	Remote Similarity	NPD8080	Discontinued
0.5725	Remote Similarity	NPD1748	Approved
0.5724	Remote Similarity	NPD5299	Approved
0.5714	Remote Similarity	NPD4264	Clinical (unspecified phase)
0.5705	Remote Similarity	NPD3648	Clinical (unspecified phase)
0.5702	Remote Similarity	NPD4819	Approved
0.5702	Remote Similarity	NPD4252	Approved
0.5702	Remote Similarity	NPD4821	Approved
0.5702	Remote Similarity	NPD7983	Approved
0.5702	Remote Similarity	NPD4822	Approved
0.5702	Remote Similarity	NPD4820	Approved
0.5683	Remote Similarity	NPD7829	Approved
0.5683	Remote Similarity	NPD7830	Approved
0.5682	Remote Similarity	NPD2204	Approved
0.5659	Remote Similarity	NPD5357	Phase 1
0.5656	Remote Similarity	NPD2252	Approved
0.5656	Remote Similarity	NPD2251	Approved
0.5655	Remote Similarity	NPD4738	Phase 2
0.5652	Remote Similarity	NPD1448	Clinical (unspecified phase)
0.5652	Remote Similarity	NPD7739	Clinical (unspecified phase)
0.5645	Remote Similarity	NPD3190	Approved
0.5645	Remote Similarity	NPD3191	Approved
0.5645	Remote Similarity	NPD3189	Approved
0.5645	Remote Similarity	NPD5349	Clinical (unspecified phase)
0.5612	Remote Similarity	NPD7624	Clinical (unspecified phase)
0.5612	Remote Similarity	NPD7623	Phase 3
0.5603	Remote Similarity	NPD2148	Clinical (unspecified phase)

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