NPASS Compound

Structure

NPC14537 OpenBabel07101718182D 24 26 0 0 1 0 0 0 0 0999 V2000 6.3916 -0.1293 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9975 0.0707 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.6485 0.5398 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.6974 0.2308 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9543 0.9000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3102 2.7682 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3127 2.6976 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8701 1.9397 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0032 0.5909 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8751 1.7984 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4326 1.0405 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2601 1.2601 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4351 0.9698 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.3090 0.9511 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.9975 0.0707 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.5000 1.5388 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0000 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.3090 0.9511 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -1.5574 -0.7579 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.5000 2.5388 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.7071 -1.7071 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.0000 -1.0000 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 5 1 0 0 0 0 5 9 1 0 0 0 0 6 7 1 0 0 0 0 6 8 1 0 0 0 0 7 10 2 0 0 0 0 8 11 1 0 0 0 0 9 12 1 0 0 0 0 10 13 1 0 0 0 0 11 13 1 0 0 0 0 12 14 1 0 0 0 0 13 15 1 1 0 0 0 14 16 1 0 0 0 0 14 18 1 6 0 0 0 15 21 1 1 0 0 0 16 20 2 0 0 0 0 16 22 1 0 0 0 0 17 19 1 0 0 0 0 17 23 2 0 0 0 0 17 24 1 0 0 0 0 18 19 1 1 0 0 0 18 24 1 0 0 0 0 19 15 1 1 0 0 0 19 20 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	335.21
Volume:	349.759
LogP:	4.084
LogD:	3.771
LogS:	-4.328
# Rotatable Bonds:	7
TPSA:	75.63
# H-Bond Aceptor:	5
# H-Bond Donor:	2
# Rings:	3
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.426
Synthetic Accessibility Score:	4.504
Fsp3:	0.789
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:	-4.632
MDCK Permeability:	3.095469219260849e-05
Pgp-inhibitor:	0.905
Pgp-substrate:	0.054
Human Intestinal Absorption (HIA):	0.011
20% Bioavailability (F20%):	0.767
30% Bioavailability (F30%):	0.912

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.857
Plasma Protein Binding (PPB):	94.25614929199219%
Volume Distribution (VD):	0.977
Pgp-substrate:	5.547638893127441%

ADMET: Metabolism

CYP1A2-inhibitor:	0.049
CYP1A2-substrate:	0.774
CYP2C19-inhibitor:	0.427
CYP2C19-substrate:	0.8
CYP2C9-inhibitor:	0.493
CYP2C9-substrate:	0.176
CYP2D6-inhibitor:	0.008
CYP2D6-substrate:	0.14
CYP3A4-inhibitor:	0.864
CYP3A4-substrate:	0.251

ADMET: Excretion

Clearance (CL):	10.437
Half-life (T1/2):	0.228

ADMET: Toxicity

hERG Blockers:	0.013
Human Hepatotoxicity (H-HT):	0.067
Drug-inuced Liver Injury (DILI):	0.045
AMES Toxicity:	0.017
Rat Oral Acute Toxicity:	0.467
Maximum Recommended Daily Dose:	0.338
Skin Sensitization:	0.381
Carcinogencity:	0.918
Eye Corrosion:	0.021
Eye Irritation:	0.03
Respiratory Toxicity:	0.502

Download Data

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

Natural Product: NPC14537

Natural Product ID:	NPC14537
*Common Name:**	Cinnabaramide A
IUPAC Name:	(1S,2R,5R)-5-[(S)-[(1S)-cyclohex-2-en-1-yl]-hydroxymethyl]-2-hexyl-1-methyl-7-oxa-4-azabicyclo[3.2.0]heptane-3,6-dione
Synonyms:
Standard InCHIKey:	KAZLTNBVAYOUNF-MUAMBBPCSA-N
Standard InCHI:	InChI=1S/C19H29NO4/c1-3-4-5-9-12-14-16(22)20-19(17(23)24-18(14,19)2)15(21)13-10-7-6-8-11-13/h7,10,13-15,21H,3-6,8-9,11-12H2,1-2H3,(H,20,22)/t13-,14+,15+,18+,19+/m1/s1
SMILES:	C[C@]12OC(=O)[C@]2([C@H]([C@H]2CCCC=C2)O)N=C([C@@H]1CCCCCC)O
Synthetic Gene Cluster:	BGC0000971;
ChEMBL Identifier:	CHEMBL384099
PubChem CID:	9862556
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	4
Others	2

Activity Type	# Activity
Cell Line	4
Others	1
PROTEIN COMPLEX	19

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT393	Cell Line	HCT-116	Homo sapiens	Activity	=	10.0	nM	PMID[496136]
NPT927	Cell Line	PBMC	Homo sapiens	IC50	=	500.0	nM	PMID[496136]
NPT82	Cell Line	MDA-MB-231	Homo sapiens	IC50	=	1000.0	nM	PMID[496136]
NPT397	Cell Line	NCI-H460	Homo sapiens	IC50	=	1000.0	nM	PMID[496136]
NPT24354	PROTEIN COMPLEX	20S proteasome	Homo sapiens	IC50	=	1.0	nM	PMID[496136]
NPT35	Others	n.a.		Stability	=	50.0	%	PMID[496136]

☑ 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 NPC14537 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	96
0.1-0.2	582
0.2-0.3	4649
0.3-0.4	20566
0.4-0.5	11372
0.5-0.6	5217
0.6-0.7	198
0.7-0.8	5
0.8-0.85	4
0.85-0.9	2
0.9-0.95	4
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9897	High Similarity	NPC473252
0.9479	High Similarity	NPC234542
0.9381	High Similarity	NPC473224
0.9271	High Similarity	NPC123141
0.9223	High Similarity	NPC12270
0.8455	Intermediate Similarity	NPC201968
0.8273	Intermediate Similarity	NPC50694
0.767	Intermediate Similarity	NPC226513
0.7193	Intermediate Similarity	NPC474725
0.7168	Intermediate Similarity	NPC475800
0.7105	Intermediate Similarity	NPC70235
0.708	Intermediate Similarity	NPC472615
0.7075	Intermediate Similarity	NPC314500
0.6991	Remote Similarity	NPC472616
0.693	Remote Similarity	NPC271269
0.6923	Remote Similarity	NPC475753
0.6903	Remote Similarity	NPC215988
0.6897	Remote Similarity	NPC473578
0.6887	Remote Similarity	NPC118193
0.6887	Remote Similarity	NPC256902
0.6863	Remote Similarity	NPC474312
0.6842	Remote Similarity	NPC74035
0.681	Remote Similarity	NPC140251
0.681	Remote Similarity	NPC307903
0.681	Remote Similarity	NPC475150
0.6783	Remote Similarity	NPC154601
0.6754	Remote Similarity	NPC474563
0.6752	Remote Similarity	NPC133729
0.6729	Remote Similarity	NPC39290
0.6729	Remote Similarity	NPC159369
0.6724	Remote Similarity	NPC251330
0.6723	Remote Similarity	NPC469865
0.6699	Remote Similarity	NPC47135
0.6698	Remote Similarity	NPC86005
0.6667	Remote Similarity	NPC165332
0.6667	Remote Similarity	NPC180722
0.6667	Remote Similarity	NPC195645
0.6638	Remote Similarity	NPC475918
0.6612	Remote Similarity	NPC471645
0.6607	Remote Similarity	NPC475438
0.6604	Remote Similarity	NPC258824
0.6585	Remote Similarity	NPC471118
0.6585	Remote Similarity	NPC471121
0.6574	Remote Similarity	NPC97577
0.6562	Remote Similarity	NPC204556
0.6555	Remote Similarity	NPC122926
0.6555	Remote Similarity	NPC113012
0.6555	Remote Similarity	NPC127578
0.6542	Remote Similarity	NPC477959
0.6512	Remote Similarity	NPC329919
0.6512	Remote Similarity	NPC477793
0.6504	Remote Similarity	NPC147707
0.6504	Remote Similarity	NPC471120
0.6504	Remote Similarity	NPC471117
0.6486	Remote Similarity	NPC5418
0.6471	Remote Similarity	NPC474891
0.6471	Remote Similarity	NPC11796
0.6471	Remote Similarity	NPC329305
0.6471	Remote Similarity	NPC218817
0.646	Remote Similarity	NPC4834
0.646	Remote Similarity	NPC167380
0.6455	Remote Similarity	NPC36491
0.6452	Remote Similarity	NPC9714
0.6446	Remote Similarity	NPC1111
0.6446	Remote Similarity	NPC261750
0.6436	Remote Similarity	NPC469514
0.6435	Remote Similarity	NPC474873
0.6429	Remote Similarity	NPC469515
0.6429	Remote Similarity	NPC54905
0.6429	Remote Similarity	NPC314009
0.6429	Remote Similarity	NPC23963
0.6417	Remote Similarity	NPC476290
0.6417	Remote Similarity	NPC46764
0.6415	Remote Similarity	NPC295799
0.6406	Remote Similarity	NPC469494
0.64	Remote Similarity	NPC323532
0.6381	Remote Similarity	NPC474252
0.6379	Remote Similarity	NPC469598
0.6378	Remote Similarity	NPC80150
0.6373	Remote Similarity	NPC281296
0.6372	Remote Similarity	NPC475503
0.6372	Remote Similarity	NPC121857
0.6372	Remote Similarity	NPC469528
0.6372	Remote Similarity	NPC469369
0.6371	Remote Similarity	NPC316325
0.6364	Remote Similarity	NPC29501
0.6364	Remote Similarity	NPC313670
0.6364	Remote Similarity	NPC473448
0.6356	Remote Similarity	NPC135216
0.6356	Remote Similarity	NPC101106
0.6346	Remote Similarity	NPC103634
0.6339	Remote Similarity	NPC473314
0.633	Remote Similarity	NPC193386
0.6327	Remote Similarity	NPC199557
0.6325	Remote Similarity	NPC4620
0.6321	Remote Similarity	NPC69469
0.6311	Remote Similarity	NPC476269
0.6311	Remote Similarity	NPC279383
0.6311	Remote Similarity	NPC268327
0.6311	Remote Similarity	NPC121200
0.6311	Remote Similarity	NPC60432
0.6311	Remote Similarity	NPC295444
0.6311	Remote Similarity	NPC7797
0.6311	Remote Similarity	NPC273215
0.63	Remote Similarity	NPC167145
0.6296	Remote Similarity	NPC116575
0.6296	Remote Similarity	NPC477994
0.6296	Remote Similarity	NPC477993
0.6293	Remote Similarity	NPC316250
0.629	Remote Similarity	NPC30196
0.6286	Remote Similarity	NPC191711
0.6271	Remote Similarity	NPC220964
0.6271	Remote Similarity	NPC119329
0.6271	Remote Similarity	NPC475676
0.6269	Remote Similarity	NPC76999
0.6262	Remote Similarity	NPC474776
0.625	Remote Similarity	NPC273185
0.625	Remote Similarity	NPC287572
0.625	Remote Similarity	NPC476049
0.625	Remote Similarity	NPC471636
0.625	Remote Similarity	NPC113363
0.6241	Remote Similarity	NPC139585
0.624	Remote Similarity	NPC6531
0.624	Remote Similarity	NPC188010
0.624	Remote Similarity	NPC476190
0.6239	Remote Similarity	NPC128501
0.6239	Remote Similarity	NPC472614
0.6239	Remote Similarity	NPC474747
0.6239	Remote Similarity	NPC477198
0.6238	Remote Similarity	NPC330016
0.6228	Remote Similarity	NPC473859
0.6226	Remote Similarity	NPC7414
0.6222	Remote Similarity	NPC75318
0.622	Remote Similarity	NPC310467
0.6216	Remote Similarity	NPC158388
0.6216	Remote Similarity	NPC478003
0.6216	Remote Similarity	NPC478004
0.6214	Remote Similarity	NPC107668
0.6214	Remote Similarity	NPC120776
0.6214	Remote Similarity	NPC240170
0.621	Remote Similarity	NPC476814
0.621	Remote Similarity	NPC476813
0.621	Remote Similarity	NPC470540
0.6207	Remote Similarity	NPC314050
0.6207	Remote Similarity	NPC315809
0.6207	Remote Similarity	NPC474718
0.6207	Remote Similarity	NPC54705
0.6204	Remote Similarity	NPC475206
0.6204	Remote Similarity	NPC125290
0.6198	Remote Similarity	NPC24389
0.6195	Remote Similarity	NPC477290
0.6194	Remote Similarity	NPC314361
0.619	Remote Similarity	NPC106791
0.619	Remote Similarity	NPC201889
0.619	Remote Similarity	NPC200446
0.6186	Remote Similarity	NPC475871
0.6186	Remote Similarity	NPC69171
0.6186	Remote Similarity	NPC475945
0.6186	Remote Similarity	NPC474165
0.6182	Remote Similarity	NPC202672
0.6182	Remote Similarity	NPC309656
0.6179	Remote Similarity	NPC66108
0.6176	Remote Similarity	NPC199445
0.6176	Remote Similarity	NPC217725
0.6176	Remote Similarity	NPC60718
0.6176	Remote Similarity	NPC145899
0.6176	Remote Similarity	NPC472430
0.6174	Remote Similarity	NPC40812
0.6174	Remote Similarity	NPC53844
0.6174	Remote Similarity	NPC475646
0.6167	Remote Similarity	NPC474421
0.6167	Remote Similarity	NPC72813
0.6167	Remote Similarity	NPC324327
0.6167	Remote Similarity	NPC250187
0.6167	Remote Similarity	NPC326994
0.6167	Remote Similarity	NPC194620
0.6161	Remote Similarity	NPC472264
0.6161	Remote Similarity	NPC184463
0.6161	Remote Similarity	NPC319473
0.6161	Remote Similarity	NPC472705
0.6161	Remote Similarity	NPC261607
0.6161	Remote Similarity	NPC111114
0.6161	Remote Similarity	NPC300312
0.6161	Remote Similarity	NPC475972
0.6154	Remote Similarity	NPC473984
0.6154	Remote Similarity	NPC472753
0.6154	Remote Similarity	NPC474742
0.6154	Remote Similarity	NPC469495
0.6154	Remote Similarity	NPC474833
0.6154	Remote Similarity	NPC127526
0.6154	Remote Similarity	NPC314451
0.6154	Remote Similarity	NPC313333
0.6154	Remote Similarity	NPC313342
0.6154	Remote Similarity	NPC175531
0.6154	Remote Similarity	NPC314512
0.6154	Remote Similarity	NPC204639
0.6147	Remote Similarity	NPC278283
0.6147	Remote Similarity	NPC476982
0.6147	Remote Similarity	NPC261721
0.6147	Remote Similarity	NPC478112

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 NPC14537 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	102
0.1-0.2	627
0.2-0.3	3629
0.3-0.4	3451
0.4-0.5	1102
0.5-0.6	213
0.6-0.7	25
0.7-0.8	0
0.8-0.85	0
0.85-0.9	0
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9223	High Similarity	NPD1719	Phase 1
0.6983	Remote Similarity	NPD6421	Discontinued
0.6983	Remote Similarity	NPD6420	Discontinued
0.6852	Remote Similarity	NPD5781	Clinical (unspecified phase)
0.6818	Remote Similarity	NPD6334	Approved
0.6818	Remote Similarity	NPD6333	Approved
0.68	Remote Similarity	NPD3732	Approved
0.6699	Remote Similarity	NPD7345	Approved
0.6697	Remote Similarity	NPD5779	Approved
0.6697	Remote Similarity	NPD5778	Approved
0.6667	Remote Similarity	NPD7839	Suspended
0.6602	Remote Similarity	NPD5369	Approved
0.6574	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6574	Remote Similarity	NPD6101	Approved
0.6518	Remote Similarity	NPD4228	Discovery
0.6455	Remote Similarity	NPD6411	Approved
0.6434	Remote Similarity	NPD8074	Phase 3
0.6381	Remote Similarity	NPD6435	Approved
0.6371	Remote Similarity	NPD7500	Approved
0.6356	Remote Similarity	NPD4211	Phase 1
0.6333	Remote Similarity	NPD6413	Approved
0.6306	Remote Similarity	NPD7983	Approved
0.6296	Remote Similarity	NPD5786	Approved
0.6288	Remote Similarity	NPD6914	Discontinued
0.6226	Remote Similarity	NPD4269	Approved
0.6226	Remote Similarity	NPD4270	Approved
0.619	Remote Similarity	NPD5368	Approved
0.6168	Remote Similarity	NPD7154	Phase 3
0.6154	Remote Similarity	NPD8342	Approved
0.6154	Remote Similarity	NPD8341	Approved
0.6154	Remote Similarity	NPD8340	Approved
0.6154	Remote Similarity	NPD8299	Approved
0.6132	Remote Similarity	NPD1448	Clinical (unspecified phase)
0.6111	Remote Similarity	NPD8137	Clinical (unspecified phase)
0.6107	Remote Similarity	NPD8451	Approved
0.6098	Remote Similarity	NPD2204	Approved
0.6098	Remote Similarity	NPD7116	Clinical (unspecified phase)
0.6061	Remote Similarity	NPD8448	Approved
0.6055	Remote Similarity	NPD5363	Approved
0.6053	Remote Similarity	NPD5282	Discontinued
0.6045	Remote Similarity	NPD8392	Approved
0.6045	Remote Similarity	NPD8391	Approved
0.6045	Remote Similarity	NPD8390	Approved
0.6038	Remote Similarity	NPD4822	Approved
0.6038	Remote Similarity	NPD4252	Approved
0.6038	Remote Similarity	NPD4820	Approved
0.6038	Remote Similarity	NPD4819	Approved
0.6038	Remote Similarity	NPD4821	Approved
0.6038	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6019	Remote Similarity	NPD5362	Discontinued
0.6018	Remote Similarity	NPD7637	Suspended
0.6	Remote Similarity	NPD4249	Approved
0.6	Remote Similarity	NPD1376	Discontinued
0.6	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6	Remote Similarity	NPD7917	Clinical (unspecified phase)
0.6	Remote Similarity	NPD7918	Clinical (unspecified phase)
0.5954	Remote Similarity	NPD7642	Approved
0.5946	Remote Similarity	NPD4250	Approved
0.5946	Remote Similarity	NPD4251	Approved
0.5938	Remote Similarity	NPD7641	Discontinued
0.5929	Remote Similarity	NPD5785	Approved
0.5929	Remote Similarity	NPD6698	Approved
0.5929	Remote Similarity	NPD46	Approved
0.5923	Remote Similarity	NPD8444	Approved
0.5923	Remote Similarity	NPD8274	Clinical (unspecified phase)
0.5912	Remote Similarity	NPD4738	Phase 2
0.5893	Remote Similarity	NPD4264	Clinical (unspecified phase)
0.5878	Remote Similarity	NPD8080	Discontinued
0.5865	Remote Similarity	NPD8273	Phase 1
0.5859	Remote Similarity	NPD7505	Discontinued
0.5849	Remote Similarity	NPD4271	Approved
0.5849	Remote Similarity	NPD4268	Approved
0.5849	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.584	Remote Similarity	NPD7601	Clinical (unspecified phase)
0.5839	Remote Similarity	NPD2613	Approved
0.5833	Remote Similarity	NPD7829	Approved
0.5833	Remote Similarity	NPD7830	Approved
0.5827	Remote Similarity	NPD2566	Approved
0.5827	Remote Similarity	NPD2574	Discontinued
0.5827	Remote Similarity	NPD2570	Approved
0.5827	Remote Similarity	NPD2573	Approved
0.5827	Remote Similarity	NPD3090	Approved
0.5827	Remote Similarity	NPD3615	Approved
0.5827	Remote Similarity	NPD2650	Approved
0.5827	Remote Similarity	NPD3088	Approved
0.5827	Remote Similarity	NPD4746	Phase 3
0.5827	Remote Similarity	NPD3614	Approved
0.5827	Remote Similarity	NPD3087	Approved
0.5827	Remote Similarity	NPD2652	Approved
0.5827	Remote Similarity	NPD3089	Approved
0.5827	Remote Similarity	NPD4745	Approved
0.5827	Remote Similarity	NPD3616	Approved
0.5827	Remote Similarity	NPD2572	Clinical (unspecified phase)
0.5827	Remote Similarity	NPD2571	Approved
0.5812	Remote Similarity	NPD5349	Clinical (unspecified phase)
0.5802	Remote Similarity	NPD6908	Approved
0.5802	Remote Similarity	NPD6909	Approved
0.5798	Remote Similarity	NPD6404	Discontinued
0.5785	Remote Similarity	NPD2259	Approved
0.5785	Remote Similarity	NPD2258	Approved
0.5755	Remote Similarity	NPD8415	Approved
0.5745	Remote Similarity	NPD4684	Phase 3
0.5745	Remote Similarity	NPD4686	Approved
0.5745	Remote Similarity	NPD4685	Phase 3
0.5728	Remote Similarity	NPD2256	Clinical (unspecified phase)
0.5691	Remote Similarity	NPD5357	Phase 1
0.569	Remote Similarity	NPD6399	Phase 3
0.5688	Remote Similarity	NPD857	Phase 3
0.5682	Remote Similarity	NPD5981	Approved
0.5682	Remote Similarity	NPD7739	Clinical (unspecified phase)
0.5682	Remote Similarity	NPD8517	Approved
0.5682	Remote Similarity	NPD8515	Approved
0.5682	Remote Similarity	NPD8513	Phase 3
0.5682	Remote Similarity	NPD8516	Approved
0.5672	Remote Similarity	NPD3131	Approved
0.5672	Remote Similarity	NPD2612	Approved
0.5672	Remote Similarity	NPD2609	Approved
0.5672	Remote Similarity	NPD2611	Approved
0.5672	Remote Similarity	NPD4217	Approved
0.5672	Remote Similarity	NPD4218	Approved
0.5672	Remote Similarity	NPD2610	Approved
0.5672	Remote Similarity	NPD2608	Approved
0.5672	Remote Similarity	NPD3132	Approved
0.5672	Remote Similarity	NPD4216	Approved
0.5672	Remote Similarity	NPD4215	Approved
0.5669	Remote Similarity	NPD6053	Discontinued
0.5662	Remote Similarity	NPD8336	Approved
0.5662	Remote Similarity	NPD8337	Approved
0.5645	Remote Similarity	NPD467	Phase 1
0.5645	Remote Similarity	NPD5697	Approved
0.5645	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.5639	Remote Similarity	NPD7624	Clinical (unspecified phase)
0.5639	Remote Similarity	NPD7623	Phase 3
0.5635	Remote Similarity	NPD6371	Approved
0.563	Remote Similarity	NPD6084	Phase 2
0.563	Remote Similarity	NPD6083	Phase 2
0.5625	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.5615	Remote Similarity	NPD6936	Clinical (unspecified phase)
0.5615	Remote Similarity	NPD6935	Phase 3
0.5612	Remote Similarity	NPD8338	Approved
0.5606	Remote Similarity	NPD6319	Approved
0.5603	Remote Similarity	NPD4810	Clinical (unspecified phase)
0.5603	Remote Similarity	NPD8387	Clinical (unspecified phase)
0.56	Remote Similarity	NPD6881	Approved
0.56	Remote Similarity	NPD6899	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