NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	210.13
Volume:	226.013
LogP:	1.356
LogD:	1.098
LogS:	-2.18
# Rotatable Bonds:	4
TPSA:	46.53
# H-Bond Aceptor:	3
# H-Bond Donor:	1
# Rings:	1
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.57
Synthetic Accessibility Score:	3.779
Fsp3:	0.583
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:	-4.474
MDCK Permeability:	4.682135840994306e-05
Pgp-inhibitor:	0.006
Pgp-substrate:	0.555
Human Intestinal Absorption (HIA):	0.005
20% Bioavailability (F20%):	0.003
30% Bioavailability (F30%):	0.03

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.777
Plasma Protein Binding (PPB):	53.369022369384766%
Volume Distribution (VD):	0.897
Pgp-substrate:	45.66411209106445%

ADMET: Metabolism

CYP1A2-inhibitor:	0.038
CYP1A2-substrate:	0.077
CYP2C19-inhibitor:	0.026
CYP2C19-substrate:	0.723
CYP2C9-inhibitor:	0.012
CYP2C9-substrate:	0.788
CYP2D6-inhibitor:	0.004
CYP2D6-substrate:	0.647
CYP3A4-inhibitor:	0.058
CYP3A4-substrate:	0.257

ADMET: Excretion

Clearance (CL):	6.266
Half-life (T1/2):	0.794

ADMET: Toxicity

hERG Blockers:	0.006
Human Hepatotoxicity (H-HT):	0.663
Drug-inuced Liver Injury (DILI):	0.341
AMES Toxicity:	0.793
Rat Oral Acute Toxicity:	0.014
Maximum Recommended Daily Dose:	0.977
Skin Sensitization:	0.928
Carcinogencity:	0.924
Eye Corrosion:	0.92
Eye Irritation:	0.922
Respiratory Toxicity:	0.959

Download Data

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

Natural Product: NPC320119

Natural Product ID:	NPC320119
*Common Name:**	Ieodomycin B
IUPAC Name:	(4S,6R)-4-hydroxy-6-[(3E)-3-methylhexa-3,5-dienyl]oxan-2-one
Synonyms:	Ieodomycin B
Standard InCHIKey:	UFMCBVUOEQAWAI-LTJOXERKSA-N
Standard InCHI:	InChI=1S/C12H18O3/c1-3-4-9(2)5-6-11-7-10(13)8-12(14)15-11/h3-4,10-11,13H,1,5-8H2,2H3/b9-4+/t10-,11+/m0/s1
SMILES:	CC(=CC=C)CCC1CC(CC(=O)O1)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1814286
PubChem CID:	53387505
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000050] Lactones [CHEMONTID:0001244] Delta valerolactones

*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
NPO30477	Bacillus sp.	Species	Bacillidae	Eukaryota	n.a.	n.a.	n.a.	PMID[19322840]
NPO30477	Bacillus sp.	Species	Bacillidae	Eukaryota	n.a.	n.a.	n.a.	PMID[21699149]
NPO30477	Bacillus sp.	Species	Bacillidae	Eukaryota	n.a.	n.a.	n.a.	PMID[22133265]
NPO30477	Bacillus sp.	Species	Bacillidae	Eukaryota	n.a.	n.a.	n.a.	PMID[8641995]
NPO30477	Bacillus sp.	Species	Bacillidae	Eukaryota	n.a.	n.a.	n.a.	PMID[9099230]

☑ 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
MIC	3

Activity Type	# Activity
Organism	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT79	Organism	Bacillus subtilis	Bacillus subtilis	MIC	=	32.0	ug.mL-1	PMID[505799]
NPT19	Organism	Escherichia coli	Escherichia coli	MIC	=	32.0	ug.mL-1	PMID[505799]
NPT312	Organism	Saccharomyces cerevisiae	Saccharomyces cerevisiae	MIC	=	256.0	ug.mL-1	PMID[505799]

☑ 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 NPC320119 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	145
0.1-0.2	1095
0.2-0.3	5988
0.3-0.4	14725
0.4-0.5	11665
0.5-0.6	7533
0.6-0.7	1403
0.7-0.8	132
0.8-0.85	9
0.85-0.9	1
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9	High Similarity	NPC326024
0.8148	Intermediate Similarity	NPC86005
0.7952	Intermediate Similarity	NPC97577
0.7945	Intermediate Similarity	NPC476660
0.7895	Intermediate Similarity	NPC190400
0.7895	Intermediate Similarity	NPC49392
0.7826	Intermediate Similarity	NPC201939
0.7821	Intermediate Similarity	NPC263574
0.7821	Intermediate Similarity	NPC469747
0.7808	Intermediate Similarity	NPC473772
0.7778	Intermediate Similarity	NPC271921
0.7778	Intermediate Similarity	NPC104537
0.7778	Intermediate Similarity	NPC127091
0.7778	Intermediate Similarity	NPC330426
0.7778	Intermediate Similarity	NPC22101
0.7778	Intermediate Similarity	NPC148192
0.7765	Intermediate Similarity	NPC36491
0.7763	Intermediate Similarity	NPC255060
0.7746	Intermediate Similarity	NPC255863
0.7746	Intermediate Similarity	NPC245947
0.7746	Intermediate Similarity	NPC136164
0.7738	Intermediate Similarity	NPC118193
0.7738	Intermediate Similarity	NPC256902
0.7711	Intermediate Similarity	NPC477959
0.7703	Intermediate Similarity	NPC477455
0.7703	Intermediate Similarity	NPC42526
0.7692	Intermediate Similarity	NPC127526
0.7681	Intermediate Similarity	NPC243532
0.7671	Intermediate Similarity	NPC141481
0.7671	Intermediate Similarity	NPC473559
0.7671	Intermediate Similarity	NPC48218
0.7671	Intermediate Similarity	NPC324981
0.7662	Intermediate Similarity	NPC239127
0.7632	Intermediate Similarity	NPC474321
0.7606	Intermediate Similarity	NPC328089
0.7606	Intermediate Similarity	NPC68343
0.7568	Intermediate Similarity	NPC317583
0.7534	Intermediate Similarity	NPC473829
0.7534	Intermediate Similarity	NPC475443
0.7532	Intermediate Similarity	NPC473948
0.7532	Intermediate Similarity	NPC60718
0.75	Intermediate Similarity	NPC326268
0.75	Intermediate Similarity	NPC476655
0.75	Intermediate Similarity	NPC103634
0.75	Intermediate Similarity	NPC318420
0.75	Intermediate Similarity	NPC476654
0.75	Intermediate Similarity	NPC476657
0.7468	Intermediate Similarity	NPC218817
0.7468	Intermediate Similarity	NPC11796
0.7468	Intermediate Similarity	NPC121200
0.7463	Intermediate Similarity	NPC52264
0.7442	Intermediate Similarity	NPC313670
0.7436	Intermediate Similarity	NPC469514
0.7416	Intermediate Similarity	NPC195645
0.7416	Intermediate Similarity	NPC180722
0.7416	Intermediate Similarity	NPC165332
0.7403	Intermediate Similarity	NPC92558
0.7403	Intermediate Similarity	NPC227396
0.7403	Intermediate Similarity	NPC476649
0.7397	Intermediate Similarity	NPC476656
0.7397	Intermediate Similarity	NPC476659
0.7381	Intermediate Similarity	NPC475753
0.7381	Intermediate Similarity	NPC116575
0.7361	Intermediate Similarity	NPC470320
0.7353	Intermediate Similarity	NPC18951
0.7342	Intermediate Similarity	NPC281296
0.7333	Intermediate Similarity	NPC143396
0.7333	Intermediate Similarity	NPC475438
0.7333	Intermediate Similarity	NPC470436
0.7333	Intermediate Similarity	NPC475004
0.7324	Intermediate Similarity	NPC328776
0.7324	Intermediate Similarity	NPC320305
0.7324	Intermediate Similarity	NPC113293
0.7313	Intermediate Similarity	NPC137538
0.7308	Intermediate Similarity	NPC469414
0.7308	Intermediate Similarity	NPC329826
0.7286	Intermediate Similarity	NPC318306
0.7284	Intermediate Similarity	NPC233377
0.7284	Intermediate Similarity	NPC469920
0.7273	Intermediate Similarity	NPC325627
0.7273	Intermediate Similarity	NPC281245
0.7273	Intermediate Similarity	NPC167145
0.726	Intermediate Similarity	NPC317881
0.726	Intermediate Similarity	NPC323045
0.7246	Intermediate Similarity	NPC225929
0.7229	Intermediate Similarity	NPC69469
0.7222	Intermediate Similarity	NPC54925
0.7215	Intermediate Similarity	NPC474447
0.7215	Intermediate Similarity	NPC12740
0.7215	Intermediate Similarity	NPC110461
0.7215	Intermediate Similarity	NPC61863
0.7206	Intermediate Similarity	NPC223677
0.7206	Intermediate Similarity	NPC10316
0.7206	Intermediate Similarity	NPC28779
0.7206	Intermediate Similarity	NPC128061
0.7206	Intermediate Similarity	NPC200845
0.7206	Intermediate Similarity	NPC228473
0.72	Intermediate Similarity	NPC474823
0.7183	Intermediate Similarity	NPC122521
0.7183	Intermediate Similarity	NPC327112
0.7183	Intermediate Similarity	NPC251042
0.7183	Intermediate Similarity	NPC174447
0.7179	Intermediate Similarity	NPC472966
0.7179	Intermediate Similarity	NPC330016
0.7176	Intermediate Similarity	NPC477993
0.7176	Intermediate Similarity	NPC477994
0.7164	Intermediate Similarity	NPC71761
0.7164	Intermediate Similarity	NPC36061
0.7164	Intermediate Similarity	NPC294548
0.7164	Intermediate Similarity	NPC1813
0.7164	Intermediate Similarity	NPC139029
0.716	Intermediate Similarity	NPC113363
0.716	Intermediate Similarity	NPC308545
0.716	Intermediate Similarity	NPC82488
0.7143	Intermediate Similarity	NPC9868
0.7143	Intermediate Similarity	NPC126061
0.7143	Intermediate Similarity	NPC70424
0.7143	Intermediate Similarity	NPC243618
0.7126	Intermediate Similarity	NPC212598
0.7125	Intermediate Similarity	NPC107668
0.7125	Intermediate Similarity	NPC120776
0.7125	Intermediate Similarity	NPC240170
0.7123	Intermediate Similarity	NPC476658
0.7123	Intermediate Similarity	NPC226592
0.7105	Intermediate Similarity	NPC236208
0.7105	Intermediate Similarity	NPC250928
0.7105	Intermediate Similarity	NPC10758
0.7101	Intermediate Similarity	NPC477201
0.7089	Intermediate Similarity	NPC260396
0.7089	Intermediate Similarity	NPC199445
0.7083	Intermediate Similarity	NPC40082
0.7083	Intermediate Similarity	NPC321838
0.7079	Intermediate Similarity	NPC478037
0.7079	Intermediate Similarity	NPC478036
0.7067	Intermediate Similarity	NPC49863
0.7067	Intermediate Similarity	NPC26500
0.7067	Intermediate Similarity	NPC99619
0.7059	Intermediate Similarity	NPC88966
0.7059	Intermediate Similarity	NPC290563
0.7059	Intermediate Similarity	NPC25417
0.7059	Intermediate Similarity	NPC85813
0.7059	Intermediate Similarity	NPC6095
0.7059	Intermediate Similarity	NPC154245
0.7059	Intermediate Similarity	NPC87564
0.7059	Intermediate Similarity	NPC261831
0.7059	Intermediate Similarity	NPC32467
0.7059	Intermediate Similarity	NPC474369
0.7059	Intermediate Similarity	NPC424
0.7059	Intermediate Similarity	NPC281972
0.7051	Intermediate Similarity	NPC144419
0.7051	Intermediate Similarity	NPC470435
0.7027	Intermediate Similarity	NPC323477
0.7027	Intermediate Similarity	NPC320642
0.7024	Intermediate Similarity	NPC16488
0.7013	Intermediate Similarity	NPC69462
0.7013	Intermediate Similarity	NPC475310
0.7011	Intermediate Similarity	NPC201046
0.7011	Intermediate Similarity	NPC472008
0.7	Intermediate Similarity	NPC266119
0.7	Intermediate Similarity	NPC5418
0.6989	Remote Similarity	NPC469871
0.6989	Remote Similarity	NPC469870
0.6988	Remote Similarity	NPC21693
0.6988	Remote Similarity	NPC117960
0.6988	Remote Similarity	NPC14044
0.6988	Remote Similarity	NPC172309
0.6988	Remote Similarity	NPC236649
0.6977	Remote Similarity	NPC315395
0.6977	Remote Similarity	NPC316426
0.6974	Remote Similarity	NPC273508
0.6974	Remote Similarity	NPC477452
0.6974	Remote Similarity	NPC218477
0.6974	Remote Similarity	NPC209327
0.6962	Remote Similarity	NPC474551
0.6944	Remote Similarity	NPC143857
0.6944	Remote Similarity	NPC229252
0.6944	Remote Similarity	NPC81896
0.6944	Remote Similarity	NPC328311
0.6944	Remote Similarity	NPC321919
0.6941	Remote Similarity	NPC474251
0.6941	Remote Similarity	NPC72464
0.6941	Remote Similarity	NPC196487
0.6941	Remote Similarity	NPC14575
0.6933	Remote Similarity	NPC328653
0.6932	Remote Similarity	NPC52198
0.6932	Remote Similarity	NPC117405
0.6923	Remote Similarity	NPC474590
0.6914	Remote Similarity	NPC145898
0.6914	Remote Similarity	NPC476325
0.6914	Remote Similarity	NPC476264
0.6912	Remote Similarity	NPC309606
0.6912	Remote Similarity	NPC139545
0.6912	Remote Similarity	NPC321062
0.6912	Remote Similarity	NPC39633
0.6912	Remote Similarity	NPC70387
0.6905	Remote Similarity	NPC474252
0.6901	Remote Similarity	NPC469373
0.6897	Remote Similarity	NPC471738
0.6889	Remote Similarity	NPC476049
0.6883	Remote Similarity	NPC107130

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 NPC320119 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	130
0.1-0.2	1526
0.2-0.3	4035
0.3-0.4	2336
0.4-0.5	740
0.5-0.6	342
0.6-0.7	33
0.7-0.8	5
0.8-0.85	3
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.7952	Intermediate Similarity	NPD5764	Clinical (unspecified phase)
0.7952	Intermediate Similarity	NPD6101	Approved
0.7765	Intermediate Similarity	NPD6411	Approved
0.7471	Intermediate Similarity	NPD5779	Approved
0.7471	Intermediate Similarity	NPD5778	Approved
0.7416	Intermediate Similarity	NPD7839	Suspended
0.7361	Intermediate Similarity	NPD3197	Phase 1
0.7356	Intermediate Similarity	NPD7983	Approved
0.7183	Intermediate Similarity	NPD4246	Clinical (unspecified phase)
0.7164	Intermediate Similarity	NPD3172	Approved
0.7108	Intermediate Similarity	NPD6435	Approved
0.7067	Intermediate Similarity	NPD4247	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD3194	Approved
0.7059	Intermediate Similarity	NPD3195	Phase 2
0.7059	Intermediate Similarity	NPD3196	Approved
0.7059	Intermediate Similarity	NPD4266	Approved
0.6867	Remote Similarity	NPD5368	Approved
0.6824	Remote Similarity	NPD7154	Phase 3
0.6786	Remote Similarity	NPD5369	Approved
0.6782	Remote Similarity	NPD5786	Approved
0.6739	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6707	Remote Similarity	NPD4756	Discovery
0.6667	Remote Similarity	NPD622	Approved
0.6667	Remote Similarity	NPD8039	Approved
0.6627	Remote Similarity	NPD3732	Approved
0.6618	Remote Similarity	NPD29	Approved
0.6618	Remote Similarity	NPD28	Approved
0.6591	Remote Similarity	NPD6422	Discontinued
0.6567	Remote Similarity	NPD3173	Approved
0.6512	Remote Similarity	NPD4270	Approved
0.6512	Remote Similarity	NPD4269	Approved
0.6494	Remote Similarity	NPD7331	Phase 2
0.6484	Remote Similarity	NPD46	Approved
0.6484	Remote Similarity	NPD6698	Approved
0.6471	Remote Similarity	NPD4252	Approved
0.6471	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6437	Remote Similarity	NPD5362	Discontinued
0.6413	Remote Similarity	NPD7637	Suspended
0.6292	Remote Similarity	NPD5363	Approved
0.6282	Remote Similarity	NPD3704	Approved
0.6235	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6235	Remote Similarity	NPD4268	Approved
0.6235	Remote Similarity	NPD4271	Approved
0.6216	Remote Similarity	NPD6109	Phase 1
0.6176	Remote Similarity	NPD5343	Approved
0.6139	Remote Similarity	NPD5048	Discontinued
0.6136	Remote Similarity	NPD5209	Approved
0.6129	Remote Similarity	NPD5785	Approved
0.6119	Remote Similarity	NPD4222	Approved
0.6119	Remote Similarity	NPD3174	Discontinued
0.6111	Remote Similarity	NPD3728	Approved
0.6111	Remote Similarity	NPD3730	Approved
0.6111	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.6105	Remote Similarity	NPD5282	Discontinued
0.6104	Remote Similarity	NPD2664	Clinical (unspecified phase)
0.6092	Remote Similarity	NPD4820	Approved
0.6092	Remote Similarity	NPD4822	Approved
0.6092	Remote Similarity	NPD4819	Approved
0.6092	Remote Similarity	NPD4821	Approved
0.6076	Remote Similarity	NPD6108	Clinical (unspecified phase)
0.6064	Remote Similarity	NPD4810	Clinical (unspecified phase)
0.6044	Remote Similarity	NPD4249	Approved
0.6022	Remote Similarity	NPD5370	Suspended
0.5981	Remote Similarity	NPD6010	Discontinued
0.5978	Remote Similarity	NPD4251	Approved
0.5978	Remote Similarity	NPD4250	Approved
0.5957	Remote Similarity	NPD7838	Discovery
0.5949	Remote Similarity	NPD7341	Phase 2
0.5946	Remote Similarity	NPD8513	Phase 3
0.5946	Remote Similarity	NPD8515	Approved
0.5946	Remote Similarity	NPD8516	Approved
0.5946	Remote Similarity	NPD8517	Approved
0.5922	Remote Similarity	NPD5697	Approved
0.5909	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.5889	Remote Similarity	NPD5332	Approved
0.5889	Remote Similarity	NPD5331	Approved
0.5882	Remote Similarity	NPD39	Approved
0.587	Remote Similarity	NPD5279	Phase 3
0.5865	Remote Similarity	NPD6899	Approved
0.5865	Remote Similarity	NPD6881	Approved
0.5859	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.5843	Remote Similarity	NPD4790	Discontinued
0.5833	Remote Similarity	NPD6399	Phase 3
0.5825	Remote Similarity	NPD5739	Approved
0.5825	Remote Similarity	NPD7128	Approved
0.5825	Remote Similarity	NPD6402	Approved
0.5825	Remote Similarity	NPD6675	Approved
0.5818	Remote Similarity	NPD7641	Discontinued
0.5814	Remote Similarity	NPD819	Approved
0.5814	Remote Similarity	NPD818	Approved
0.5811	Remote Similarity	NPD4627	Clinical (unspecified phase)
0.581	Remote Similarity	NPD6012	Approved
0.581	Remote Similarity	NPD6014	Approved
0.581	Remote Similarity	NPD6013	Approved
0.5806	Remote Similarity	NPD3573	Approved
0.5804	Remote Similarity	NPD8444	Approved
0.5778	Remote Similarity	NPD3667	Approved
0.5773	Remote Similarity	NPD7748	Approved
0.5769	Remote Similarity	NPD5701	Approved
0.5761	Remote Similarity	NPD1694	Approved
0.5761	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.5758	Remote Similarity	NPD6084	Phase 2
0.5758	Remote Similarity	NPD6083	Phase 2
0.5755	Remote Similarity	NPD7102	Approved
0.5755	Remote Similarity	NPD7290	Approved
0.5755	Remote Similarity	NPD6883	Approved
0.575	Remote Similarity	NPD2685	Clinical (unspecified phase)
0.5735	Remote Similarity	NPD6096	Approved
0.5735	Remote Similarity	NPD2699	Approved
0.5735	Remote Similarity	NPD6097	Approved
0.5729	Remote Similarity	NPD6079	Approved
0.5729	Remote Similarity	NPD7515	Phase 2
0.5714	Remote Similarity	NPD7320	Approved
0.5714	Remote Similarity	NPD6011	Approved
0.5714	Remote Similarity	NPD5695	Phase 3
0.5702	Remote Similarity	NPD7830	Approved
0.5702	Remote Similarity	NPD7829	Approved
0.5701	Remote Similarity	NPD1719	Phase 1
0.5701	Remote Similarity	NPD6847	Approved
0.5701	Remote Similarity	NPD6649	Approved
0.5701	Remote Similarity	NPD8130	Phase 1
0.5701	Remote Similarity	NPD6650	Approved
0.5701	Remote Similarity	NPD6617	Approved
0.5701	Remote Similarity	NPD6869	Approved
0.57	Remote Similarity	NPD4225	Approved
0.5699	Remote Similarity	NPD5330	Approved
0.5699	Remote Similarity	NPD7521	Approved
0.5699	Remote Similarity	NPD6409	Approved
0.5699	Remote Similarity	NPD6684	Approved
0.5699	Remote Similarity	NPD7146	Approved
0.5699	Remote Similarity	NPD7334	Approved
0.5694	Remote Similarity	NPD6927	Phase 3
0.569	Remote Similarity	NPD8074	Phase 3
0.5684	Remote Similarity	NPD5328	Approved
0.5676	Remote Similarity	NPD3729	Clinical (unspecified phase)
0.5667	Remote Similarity	NPD226	Approved
0.566	Remote Similarity	NPD6372	Approved
0.566	Remote Similarity	NPD6373	Approved
0.5658	Remote Similarity	NPD8959	Approved
0.5652	Remote Similarity	NPD8341	Approved
0.5652	Remote Similarity	NPD3133	Approved
0.5652	Remote Similarity	NPD8340	Approved
0.5652	Remote Similarity	NPD4786	Approved
0.5652	Remote Similarity	NPD8299	Approved
0.5652	Remote Similarity	NPD3665	Phase 1
0.5652	Remote Similarity	NPD8342	Approved
0.5652	Remote Similarity	NPD3666	Approved
0.5648	Remote Similarity	NPD6882	Approved
0.5648	Remote Similarity	NPD8297	Approved
0.5631	Remote Similarity	NPD6647	Phase 2
0.5625	Remote Similarity	NPD3673	Approved
0.5625	Remote Similarity	NPD5325	Clinical (unspecified phase)
0.5625	Remote Similarity	NPD3672	Approved
0.5619	Remote Similarity	NPD6685	Approved
0.5604	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.5603	Remote Similarity	NPD8451	Approved
0.56	Remote Similarity	NPD7902	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