NPASS Compound

Structure

NPC176215 OpenBabel07101718192D 25 24 0 0 1 0 0 0 0 0999 V2000 12.9904 8.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 12.9904 7.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 12.1244 7.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 11.2583 7.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 10.3923 7.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.5263 7.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.6603 7.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.7942 7.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9282 7.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 7.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 7.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 5.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 7.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 6.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 7.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.7321 1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 7.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 0 0 0 2 3 1 0 0 0 0 3 4 1 0 0 0 0 4 5 1 0 0 0 0 5 6 1 0 0 0 0 6 7 1 0 0 0 0 7 8 1 0 0 0 0 8 9 1 0 0 0 0 9 10 1 0 0 0 0 10 12 1 0 0 0 0 11 13 1 0 0 0 0 11 14 1 0 0 0 0 12 15 1 0 0 0 0 13 16 2 0 0 0 0 14 17 1 0 0 0 0 15 20 1 0 0 0 0 16 20 1 0 0 0 0 17 25 1 0 0 0 0 18 21 1 0 0 0 0 18 22 1 0 0 0 0 19 21 1 0 0 0 0 19 25 1 0 0 0 0 20 23 2 0 0 0 0 21 24 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	356.29
Volume:	401.66
LogP:	4.815
LogD:	3.816
LogS:	-4.2
# Rotatable Bonds:	19
TPSA:	66.76
# H-Bond Aceptor:	4
# H-Bond Donor:	2
# Rings:	0
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.263
Synthetic Accessibility Score:	2.897
Fsp3:	0.857
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
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:	-4.767
MDCK Permeability:	2.7031905119656585e-05
Pgp-inhibitor:	0.376
Pgp-substrate:	0.765
Human Intestinal Absorption (HIA):	0.005
20% Bioavailability (F20%):	0.984
30% Bioavailability (F30%):	0.546

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.129
Plasma Protein Binding (PPB):	97.2308120727539%
Volume Distribution (VD):	0.751
Pgp-substrate:	1.54379141330719%

ADMET: Metabolism

CYP1A2-inhibitor:	0.152
CYP1A2-substrate:	0.149
CYP2C19-inhibitor:	0.288
CYP2C19-substrate:	0.064
CYP2C9-inhibitor:	0.343
CYP2C9-substrate:	0.377
CYP2D6-inhibitor:	0.005
CYP2D6-substrate:	0.051
CYP3A4-inhibitor:	0.406
CYP3A4-substrate:	0.066

ADMET: Excretion

Clearance (CL):	8.034
Half-life (T1/2):	0.688

ADMET: Toxicity

hERG Blockers:	0.169
Human Hepatotoxicity (H-HT):	0.417
Drug-inuced Liver Injury (DILI):	0.017
AMES Toxicity:	0.098
Rat Oral Acute Toxicity:	0.052
Maximum Recommended Daily Dose:	0.11
Skin Sensitization:	0.965
Carcinogencity:	0.432
Eye Corrosion:	0.362
Eye Irritation:	0.86
Respiratory Toxicity:	0.929

Download Data

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

Natural Product: NPC176215

Natural Product ID:	NPC176215
*Common Name:**	Niphatenone B
IUPAC Name:	(E)-1-[(2S)-2,3-dihydroxypropoxy]octadec-4-en-6-one
Synonyms:	Niphatenone B
Standard InCHIKey:	UJRKZHMKHFVGBP-WMJZSHNHSA-N
Standard InCHI:	InChI=1S/C21H40O4/c1-2-3-4-5-6-7-8-9-10-12-15-20(23)16-13-11-14-17-25-19-21(24)18-22/h13,16,21-22,24H,2-12,14-15,17-19H2,1H3/b16-13+/t21-/m0/s1
SMILES:	CCCCCCCCCCCCC(=O)/C=C/CCCOC[C@H](CO)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1946012
PubChem CID:	56946740
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000175] Glycerolipids [CHEMONTID:0003808] Monoradylglycerols [CHEMONTID:0003263] Monoalkylglycerols

*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
NPO20398	Niphates digitalis	Species	Niphatidae	Eukaryota	n.a.	n.a.	n.a.	PMID[22148427]
NPO20398	Niphates digitalis	Species	Niphatidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

☑ 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
Others	1

Activity Type	# Activity
Individual Protein	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT153	Individual Protein	Androgen Receptor	Homo sapiens	Inhibition	=	50.0	%	PMID[496867]

☑ 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 NPC176215 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	160
0.1-0.2	2334
0.2-0.3	9651
0.3-0.4	17384
0.4-0.5	8571
0.5-0.6	3656
0.6-0.7	849
0.7-0.8	66
0.8-0.85	22
0.85-0.9	1
0.9-0.95	1
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC296436
0.9206	High Similarity	NPC83965
0.8824	High Similarity	NPC474321
0.8485	Intermediate Similarity	NPC127091
0.8485	Intermediate Similarity	NPC271921
0.8485	Intermediate Similarity	NPC330426
0.8485	Intermediate Similarity	NPC22101
0.8485	Intermediate Similarity	NPC104537
0.8485	Intermediate Similarity	NPC148192
0.8358	Intermediate Similarity	NPC141481
0.8358	Intermediate Similarity	NPC324981
0.8358	Intermediate Similarity	NPC473559
0.8358	Intermediate Similarity	NPC48218
0.8209	Intermediate Similarity	NPC475443
0.8209	Intermediate Similarity	NPC473829
0.8182	Intermediate Similarity	NPC476657
0.8182	Intermediate Similarity	NPC476655
0.8182	Intermediate Similarity	NPC476654
0.8125	Intermediate Similarity	NPC81896
0.8125	Intermediate Similarity	NPC321919
0.8116	Intermediate Similarity	NPC476660
0.8116	Intermediate Similarity	NPC42526
0.806	Intermediate Similarity	NPC476656
0.806	Intermediate Similarity	NPC476659
0.803	Intermediate Similarity	NPC476658
0.7971	Intermediate Similarity	NPC473772
0.7826	Intermediate Similarity	NPC273508
0.7826	Intermediate Similarity	NPC209327
0.7612	Intermediate Similarity	NPC54925
0.7606	Intermediate Similarity	NPC477455
0.7576	Intermediate Similarity	NPC229252
0.7576	Intermediate Similarity	NPC143857
0.7541	Intermediate Similarity	NPC477458
0.75	Intermediate Similarity	NPC475221
0.7465	Intermediate Similarity	NPC143396
0.7465	Intermediate Similarity	NPC475982
0.7463	Intermediate Similarity	NPC321838
0.7463	Intermediate Similarity	NPC201939
0.7429	Intermediate Similarity	NPC99619
0.7429	Intermediate Similarity	NPC26500
0.7424	Intermediate Similarity	NPC106851
0.7424	Intermediate Similarity	NPC274927
0.7403	Intermediate Similarity	NPC472948
0.7385	Intermediate Similarity	NPC323436
0.7342	Intermediate Similarity	NPC144415
0.7342	Intermediate Similarity	NPC253801
0.7313	Intermediate Similarity	NPC243532
0.7297	Intermediate Similarity	NPC160540
0.7286	Intermediate Similarity	NPC137163
0.7284	Intermediate Similarity	NPC477015
0.725	Intermediate Similarity	NPC163093
0.7246	Intermediate Similarity	NPC68343
0.7246	Intermediate Similarity	NPC328089
0.7215	Intermediate Similarity	NPC473712
0.7215	Intermediate Similarity	NPC94875
0.7215	Intermediate Similarity	NPC180363
0.7215	Intermediate Similarity	NPC65930
0.7215	Intermediate Similarity	NPC473529
0.7215	Intermediate Similarity	NPC473780
0.7215	Intermediate Similarity	NPC145914
0.7215	Intermediate Similarity	NPC11332
0.7215	Intermediate Similarity	NPC73310
0.7215	Intermediate Similarity	NPC475159
0.7215	Intermediate Similarity	NPC131002
0.7215	Intermediate Similarity	NPC329829
0.7206	Intermediate Similarity	NPC64971
0.7206	Intermediate Similarity	NPC168407
0.7206	Intermediate Similarity	NPC40082
0.72	Intermediate Similarity	NPC260396
0.7183	Intermediate Similarity	NPC478100
0.7183	Intermediate Similarity	NPC25298
0.716	Intermediate Similarity	NPC477013
0.716	Intermediate Similarity	NPC120398
0.716	Intermediate Similarity	NPC477014
0.716	Intermediate Similarity	NPC322529
0.716	Intermediate Similarity	NPC471567
0.7143	Intermediate Similarity	NPC218817
0.7143	Intermediate Similarity	NPC473471
0.7143	Intermediate Similarity	NPC11796
0.7125	Intermediate Similarity	NPC477786
0.7125	Intermediate Similarity	NPC477784
0.7125	Intermediate Similarity	NPC477785
0.7123	Intermediate Similarity	NPC94743
0.7123	Intermediate Similarity	NPC291062
0.7108	Intermediate Similarity	NPC476707
0.7108	Intermediate Similarity	NPC476706
0.7105	Intermediate Similarity	NPC470899
0.7105	Intermediate Similarity	NPC190400
0.7105	Intermediate Similarity	NPC49392
0.7097	Intermediate Similarity	NPC288381
0.7097	Intermediate Similarity	NPC20934
0.7097	Intermediate Similarity	NPC225974
0.7089	Intermediate Similarity	NPC21693
0.7089	Intermediate Similarity	NPC236649
0.7089	Intermediate Similarity	NPC280367
0.7073	Intermediate Similarity	NPC69082
0.7073	Intermediate Similarity	NPC279267
0.7073	Intermediate Similarity	NPC308412
0.7073	Intermediate Similarity	NPC210218
0.7073	Intermediate Similarity	NPC204686
0.7073	Intermediate Similarity	NPC473687
0.7073	Intermediate Similarity	NPC309211
0.7073	Intermediate Similarity	NPC477010
0.7073	Intermediate Similarity	NPC134885
0.7073	Intermediate Similarity	NPC134807
0.7073	Intermediate Similarity	NPC219498
0.7067	Intermediate Similarity	NPC227396
0.7059	Intermediate Similarity	NPC122521
0.7059	Intermediate Similarity	NPC251042
0.7059	Intermediate Similarity	NPC235242
0.7059	Intermediate Similarity	NPC174447
0.7042	Intermediate Similarity	NPC478101
0.7037	Intermediate Similarity	NPC156804
0.7024	Intermediate Similarity	NPC477016
0.7024	Intermediate Similarity	NPC280612
0.7024	Intermediate Similarity	NPC477017
0.7013	Intermediate Similarity	NPC176329
0.7013	Intermediate Similarity	NPC51809
0.7013	Intermediate Similarity	NPC474818
0.7013	Intermediate Similarity	NPC125365
0.7013	Intermediate Similarity	NPC49302
0.6988	Remote Similarity	NPC178215
0.6988	Remote Similarity	NPC477012
0.6986	Remote Similarity	NPC130618
0.6986	Remote Similarity	NPC94488
0.6986	Remote Similarity	NPC262673
0.697	Remote Similarity	NPC477201
0.697	Remote Similarity	NPC325977
0.6962	Remote Similarity	NPC47653
0.6957	Remote Similarity	NPC260573
0.6957	Remote Similarity	NPC328776
0.6957	Remote Similarity	NPC320305
0.6951	Remote Similarity	NPC473671
0.6951	Remote Similarity	NPC329838
0.6951	Remote Similarity	NPC132496
0.6951	Remote Similarity	NPC473156
0.6951	Remote Similarity	NPC77871
0.6951	Remote Similarity	NPC473651
0.6951	Remote Similarity	NPC82795
0.6951	Remote Similarity	NPC182383
0.6951	Remote Similarity	NPC286338
0.6951	Remote Similarity	NPC66346
0.6951	Remote Similarity	NPC473478
0.6951	Remote Similarity	NPC473669
0.6951	Remote Similarity	NPC319036
0.6951	Remote Similarity	NPC292809
0.6951	Remote Similarity	NPC103284
0.6951	Remote Similarity	NPC477018
0.6951	Remote Similarity	NPC39279
0.6951	Remote Similarity	NPC223871
0.6951	Remote Similarity	NPC1083
0.6951	Remote Similarity	NPC39167
0.6951	Remote Similarity	NPC235809
0.6951	Remote Similarity	NPC202055
0.6951	Remote Similarity	NPC329615
0.6951	Remote Similarity	NPC475268
0.6951	Remote Similarity	NPC283085
0.6951	Remote Similarity	NPC107986
0.6951	Remote Similarity	NPC9678
0.6951	Remote Similarity	NPC100921
0.6951	Remote Similarity	NPC231009
0.6951	Remote Similarity	NPC25764
0.6951	Remote Similarity	NPC470400
0.6951	Remote Similarity	NPC110710
0.6944	Remote Similarity	NPC478097
0.6941	Remote Similarity	NPC478003
0.6941	Remote Similarity	NPC158388
0.6941	Remote Similarity	NPC478004
0.6933	Remote Similarity	NPC470435
0.6923	Remote Similarity	NPC221095
0.6923	Remote Similarity	NPC248775
0.6923	Remote Similarity	NPC231739
0.6923	Remote Similarity	NPC300121
0.6923	Remote Similarity	NPC192006
0.6923	Remote Similarity	NPC182292
0.6923	Remote Similarity	NPC279214
0.6914	Remote Similarity	NPC473500
0.6914	Remote Similarity	NPC284472
0.6914	Remote Similarity	NPC38295
0.6914	Remote Similarity	NPC286770
0.6914	Remote Similarity	NPC229799
0.6914	Remote Similarity	NPC156089
0.6914	Remote Similarity	NPC470313
0.6912	Remote Similarity	NPC278202
0.6912	Remote Similarity	NPC473652
0.6905	Remote Similarity	NPC21208
0.6905	Remote Similarity	NPC89001
0.6905	Remote Similarity	NPC233551
0.6905	Remote Similarity	NPC476708
0.6905	Remote Similarity	NPC476704
0.6905	Remote Similarity	NPC320458
0.6905	Remote Similarity	NPC280621
0.6905	Remote Similarity	NPC40376
0.6905	Remote Similarity	NPC473905
0.6905	Remote Similarity	NPC48338
0.6905	Remote Similarity	NPC20339
0.6901	Remote Similarity	NPC255863
0.6901	Remote Similarity	NPC318420
0.6901	Remote Similarity	NPC326268
0.6901	Remote Similarity	NPC136164

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 NPC176215 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	136
0.1-0.2	3067
0.2-0.3	4019
0.3-0.4	1395
0.4-0.5	395
0.5-0.6	110
0.6-0.7	27
0.7-0.8	1
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
0.75	Intermediate Similarity	NPD3197	Phase 1
0.7015	Intermediate Similarity	NPD6109	Phase 1
0.6667	Remote Similarity	NPD3195	Phase 2
0.6667	Remote Similarity	NPD3730	Approved
0.6667	Remote Similarity	NPD4266	Approved
0.6667	Remote Similarity	NPD3728	Approved
0.6667	Remote Similarity	NPD3196	Approved
0.6667	Remote Similarity	NPD3194	Approved
0.662	Remote Similarity	NPD2664	Clinical (unspecified phase)
0.6585	Remote Similarity	NPD6435	Approved
0.6575	Remote Similarity	NPD6108	Clinical (unspecified phase)
0.6575	Remote Similarity	NPD3704	Approved
0.6571	Remote Similarity	NPD4246	Clinical (unspecified phase)
0.6567	Remote Similarity	NPD4627	Clinical (unspecified phase)
0.6552	Remote Similarity	NPD6698	Approved
0.6552	Remote Similarity	NPD46	Approved
0.6515	Remote Similarity	NPD3172	Approved
0.6353	Remote Similarity	NPD5363	Approved
0.6351	Remote Similarity	NPD7331	Phase 2
0.6341	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.6341	Remote Similarity	NPD5368	Approved
0.631	Remote Similarity	NPD7154	Phase 3
0.6296	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6292	Remote Similarity	NPD7983	Approved
0.6286	Remote Similarity	NPD585	Clinical (unspecified phase)
0.6267	Remote Similarity	NPD4247	Clinical (unspecified phase)
0.6265	Remote Similarity	NPD5369	Approved
0.625	Remote Similarity	NPD5343	Approved
0.6212	Remote Similarity	NPD28	Approved
0.6212	Remote Similarity	NPD29	Approved
0.619	Remote Similarity	NPD39	Approved
0.618	Remote Similarity	NPD7838	Discovery
0.618	Remote Similarity	NPD5785	Approved
0.6173	Remote Similarity	NPD4756	Discovery
0.6154	Remote Similarity	NPD3173	Approved
0.6145	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6145	Remote Similarity	NPD4252	Approved
0.6118	Remote Similarity	NPD6110	Phase 1
0.6049	Remote Similarity	NPD818	Approved
0.6049	Remote Similarity	NPD819	Approved
0.6032	Remote Similarity	NPD6096	Approved
0.6032	Remote Similarity	NPD6097	Approved
0.6	Remote Similarity	NPD4269	Approved
0.6	Remote Similarity	NPD4270	Approved
0.5938	Remote Similarity	NPD4222	Approved
0.593	Remote Similarity	NPD5362	Discontinued
0.5914	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.5909	Remote Similarity	NPD5786	Approved
0.5904	Remote Similarity	NPD4268	Approved
0.5904	Remote Similarity	NPD4271	Approved
0.5889	Remote Similarity	NPD6101	Approved
0.5889	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.5873	Remote Similarity	NPD5326	Phase 3
0.5806	Remote Similarity	NPD5282	Discontinued
0.58	Remote Similarity	NPD6412	Phase 2
0.5789	Remote Similarity	NPD7341	Phase 2
0.5784	Remote Similarity	NPD6371	Approved
0.5765	Remote Similarity	NPD4821	Approved
0.5765	Remote Similarity	NPD4822	Approved
0.5765	Remote Similarity	NPD4820	Approved
0.5765	Remote Similarity	NPD4819	Approved
0.5761	Remote Similarity	NPD6079	Approved
0.5761	Remote Similarity	NPD6411	Approved
0.5758	Remote Similarity	NPD6125	Clinical (unspecified phase)
0.5758	Remote Similarity	NPD622	Approved
0.5743	Remote Similarity	NPD6686	Approved
0.5733	Remote Similarity	NPD3210	Clinical (unspecified phase)
0.5714	Remote Similarity	NPD3732	Approved
0.5699	Remote Similarity	NPD5779	Approved
0.5699	Remote Similarity	NPD5778	Approved
0.5694	Remote Similarity	NPD8779	Phase 3
0.5692	Remote Similarity	NPD3174	Discontinued
0.5682	Remote Similarity	NPD3133	Approved
0.5682	Remote Similarity	NPD3665	Phase 1
0.5682	Remote Similarity	NPD3666	Approved
0.5673	Remote Similarity	NPD8297	Approved
0.5667	Remote Similarity	NPD4250	Approved
0.5667	Remote Similarity	NPD4251	Approved
0.5644	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.5638	Remote Similarity	NPD7748	Approved
0.5632	Remote Similarity	NPD5209	Approved
0.5625	Remote Similarity	NPD6084	Phase 2
0.5625	Remote Similarity	NPD6083	Phase 2
0.5607	Remote Similarity	NPD7115	Discovery

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