NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	364.26
Volume:	405.127
LogP:	5.079
LogD:	3.88
LogS:	-3.302
# Rotatable Bonds:	14
TPSA:	80.92
# H-Bond Aceptor:	4
# H-Bond Donor:	4
# Rings:	1
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.139
Synthetic Accessibility Score:	3.004
Fsp3:	0.636
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.0
MDCK Permeability:	2.4437016691081226e-05
Pgp-inhibitor:	0.001
Pgp-substrate:	0.004
Human Intestinal Absorption (HIA):	0.09
20% Bioavailability (F20%):	1.0
30% Bioavailability (F30%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.01
Plasma Protein Binding (PPB):	99.4477310180664%
Volume Distribution (VD):	3.418
Pgp-substrate:	0.6097217798233032%

ADMET: Metabolism

CYP1A2-inhibitor:	0.346
CYP1A2-substrate:	0.452
CYP2C19-inhibitor:	0.585
CYP2C19-substrate:	0.1
CYP2C9-inhibitor:	0.221
CYP2C9-substrate:	0.973
CYP2D6-inhibitor:	0.777
CYP2D6-substrate:	0.803
CYP3A4-inhibitor:	0.143
CYP3A4-substrate:	0.084

ADMET: Excretion

Clearance (CL):	5.334
Half-life (T1/2):	0.915

ADMET: Toxicity

hERG Blockers:	0.032
Human Hepatotoxicity (H-HT):	0.028
Drug-inuced Liver Injury (DILI):	0.014
AMES Toxicity:	0.54
Rat Oral Acute Toxicity:	0.098
Maximum Recommended Daily Dose:	0.273
Skin Sensitization:	0.972
Carcinogencity:	0.067
Eye Corrosion:	0.005
Eye Irritation:	0.938
Respiratory Toxicity:	0.661

Download Data

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

Natural Product: NPC477708

Natural Product ID:	NPC477708
*Common Name:**	Trineurone E
IUPAC Name:	(4R)-2-[(Z)-hexadec-10-enoyl]-3,4-dihydroxycyclohex-2-en-1-one
Synonyms:
Standard InCHIKey:	SQTQWFVWUFUZIO-PXDRNWIDSA-N
Standard InCHI:	InChI=1S/C22H36O4/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-18(23)21-19(24)16-17-20(25)22(21)26/h6-7,20,25-26H,2-5,8-17H2,1H3/b7-6-/t20-/m1/s1
SMILES:	CCCCC/C=C\CCCCCCCCC(=O)C1=C([C@@H](CCC1=O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3289513
PubChem CID:	90681785
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds]

*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
NPO33674	Peperomia trineura	Species	Piperaceae	Eukaryota	aerial parts	Encantado, Rio Grande do Sul, Brazil	2006-DEC	PMID[24905499]

☑ 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	2
Others	2

Activity Type	# Activity
Cell Line	1
Organism	2
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT111	Cell Line	K562	Homo sapiens	IC50	=	26000	nM	PMID[24905499]
NPT487	Organism	Cladosporium cladosporioides	Cladosporium cladosporioides	Activity	=	1	ug	PMID[24905499]
NPT488	Organism	Cladosporium sphaerospermum	Cladosporium sphaerospermum	Activity	=	10	ug	PMID[24905499]
NPT2	Others	Unspecified		IC50	=	14300	nM	PMID[24905499]

☑ 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 NPC477708 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	166
0.1-0.2	1585
0.2-0.3	7510
0.3-0.4	17167
0.4-0.5	9571
0.5-0.6	5245
0.6-0.7	1333
0.7-0.8	102
0.8-0.85	17
0.85-0.9	0
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.8286	Intermediate Similarity	NPC477707
0.8243	Intermediate Similarity	NPC94743
0.8243	Intermediate Similarity	NPC291062
0.8169	Intermediate Similarity	NPC7029
0.8108	Intermediate Similarity	NPC262673
0.8028	Intermediate Similarity	NPC143168
0.8028	Intermediate Similarity	NPC53109
0.8028	Intermediate Similarity	NPC477830
0.7973	Intermediate Similarity	NPC263382
0.7973	Intermediate Similarity	NPC125578
0.7973	Intermediate Similarity	NPC146376
0.7973	Intermediate Similarity	NPC477452
0.7952	Intermediate Similarity	NPC77971
0.7922	Intermediate Similarity	NPC264178
0.7907	Intermediate Similarity	NPC471399
0.7867	Intermediate Similarity	NPC94488
0.7848	Intermediate Similarity	NPC473536
0.7838	Intermediate Similarity	NPC474619
0.7838	Intermediate Similarity	NPC243272
0.7816	Intermediate Similarity	NPC146852
0.775	Intermediate Similarity	NPC231739
0.7727	Intermediate Similarity	NPC61275
0.7703	Intermediate Similarity	NPC16119
0.7568	Intermediate Similarity	NPC98897
0.75	Intermediate Similarity	NPC477786
0.75	Intermediate Similarity	NPC477784
0.75	Intermediate Similarity	NPC477785
0.7465	Intermediate Similarity	NPC320421
0.7432	Intermediate Similarity	NPC474400
0.7432	Intermediate Similarity	NPC34622
0.7407	Intermediate Similarity	NPC471061
0.7349	Intermediate Similarity	NPC74086
0.7317	Intermediate Similarity	NPC248624
0.7308	Intermediate Similarity	NPC173321
0.7308	Intermediate Similarity	NPC477455
0.7303	Intermediate Similarity	NPC469464
0.7297	Intermediate Similarity	NPC151728
0.7297	Intermediate Similarity	NPC57463
0.726	Intermediate Similarity	NPC243532
0.725	Intermediate Similarity	NPC227396
0.7204	Intermediate Similarity	NPC273269
0.7204	Intermediate Similarity	NPC20066
0.7179	Intermediate Similarity	NPC10758
0.7179	Intermediate Similarity	NPC250928
0.7176	Intermediate Similarity	NPC47450
0.7174	Intermediate Similarity	NPC279313
0.7174	Intermediate Similarity	NPC91408
0.7162	Intermediate Similarity	NPC201939
0.7143	Intermediate Similarity	NPC91332
0.7143	Intermediate Similarity	NPC251429
0.7143	Intermediate Similarity	NPC162741
0.7128	Intermediate Similarity	NPC300584
0.7126	Intermediate Similarity	NPC32037
0.7108	Intermediate Similarity	NPC478122
0.7059	Intermediate Similarity	NPC275766
0.7053	Intermediate Similarity	NPC46761
0.7051	Intermediate Similarity	NPC134385
0.7045	Intermediate Similarity	NPC94666
0.7045	Intermediate Similarity	NPC183736
0.7013	Intermediate Similarity	NPC137163
0.7013	Intermediate Similarity	NPC83965
0.7011	Intermediate Similarity	NPC474251
0.6988	Remote Similarity	NPC82666
0.6988	Remote Similarity	NPC97173
0.6977	Remote Similarity	NPC103486
0.6966	Remote Similarity	NPC471738
0.6966	Remote Similarity	NPC472007
0.6962	Remote Similarity	NPC143396
0.6962	Remote Similarity	NPC469914
0.6951	Remote Similarity	NPC175079
0.6941	Remote Similarity	NPC470945
0.6941	Remote Similarity	NPC470946
0.6941	Remote Similarity	NPC470947
0.6933	Remote Similarity	NPC321838
0.6932	Remote Similarity	NPC187529
0.6932	Remote Similarity	NPC79573
0.6932	Remote Similarity	NPC36350
0.6923	Remote Similarity	NPC99619
0.6923	Remote Similarity	NPC96962
0.6923	Remote Similarity	NPC26500
0.6905	Remote Similarity	NPC321180
0.6905	Remote Similarity	NPC475994
0.6897	Remote Similarity	NPC1761
0.6897	Remote Similarity	NPC52609
0.6892	Remote Similarity	NPC106851
0.6892	Remote Similarity	NPC274927
0.6892	Remote Similarity	NPC473494
0.6889	Remote Similarity	NPC472008
0.6883	Remote Similarity	NPC474304
0.6883	Remote Similarity	NPC176215
0.6883	Remote Similarity	NPC474329
0.6883	Remote Similarity	NPC296436
0.6882	Remote Similarity	NPC23170
0.6875	Remote Similarity	NPC318766
0.6875	Remote Similarity	NPC42526
0.686	Remote Similarity	NPC67254
0.6854	Remote Similarity	NPC472009
0.6854	Remote Similarity	NPC203795
0.6849	Remote Similarity	NPC192843
0.6849	Remote Similarity	NPC281230
0.6848	Remote Similarity	NPC99380
0.6837	Remote Similarity	NPC320294
0.6829	Remote Similarity	NPC474321
0.6829	Remote Similarity	NPC215050
0.6824	Remote Similarity	NPC19900
0.6818	Remote Similarity	NPC40687
0.6818	Remote Similarity	NPC469809
0.6804	Remote Similarity	NPC470184
0.6786	Remote Similarity	NPC47844
0.6786	Remote Similarity	NPC197659
0.6786	Remote Similarity	NPC141195
0.6786	Remote Similarity	NPC211279
0.6782	Remote Similarity	NPC38796
0.6782	Remote Similarity	NPC158411
0.6782	Remote Similarity	NPC212083
0.6782	Remote Similarity	NPC279186
0.6782	Remote Similarity	NPC48362
0.6778	Remote Similarity	NPC472324
0.6774	Remote Similarity	NPC109414
0.6774	Remote Similarity	NPC211230
0.6771	Remote Similarity	NPC35717
0.6771	Remote Similarity	NPC306908
0.6753	Remote Similarity	NPC328089
0.6753	Remote Similarity	NPC68343
0.675	Remote Similarity	NPC236208
0.6747	Remote Similarity	NPC114236
0.6747	Remote Similarity	NPC474011
0.6747	Remote Similarity	NPC472256
0.6744	Remote Similarity	NPC172013
0.6744	Remote Similarity	NPC2482
0.6742	Remote Similarity	NPC182383
0.6742	Remote Similarity	NPC476426
0.6742	Remote Similarity	NPC28887
0.6742	Remote Similarity	NPC470177
0.6739	Remote Similarity	NPC166554
0.6739	Remote Similarity	NPC477684
0.6739	Remote Similarity	NPC472325
0.6739	Remote Similarity	NPC265856
0.6739	Remote Similarity	NPC128672
0.6739	Remote Similarity	NPC131864
0.6739	Remote Similarity	NPC134321
0.6714	Remote Similarity	NPC477458
0.6712	Remote Similarity	NPC477201
0.6711	Remote Similarity	NPC40082
0.6709	Remote Similarity	NPC148192
0.6709	Remote Similarity	NPC330426
0.6709	Remote Similarity	NPC127091
0.6709	Remote Similarity	NPC104537
0.6709	Remote Similarity	NPC271921
0.6709	Remote Similarity	NPC22101
0.6709	Remote Similarity	NPC106613
0.6707	Remote Similarity	NPC186042
0.6706	Remote Similarity	NPC192006
0.6706	Remote Similarity	NPC178852
0.6705	Remote Similarity	NPC62214
0.6705	Remote Similarity	NPC185256
0.6703	Remote Similarity	NPC470524
0.6703	Remote Similarity	NPC185059
0.6703	Remote Similarity	NPC475001
0.6703	Remote Similarity	NPC53454
0.6702	Remote Similarity	NPC245972
0.6702	Remote Similarity	NPC212812
0.6702	Remote Similarity	NPC103527
0.6702	Remote Similarity	NPC474328
0.6702	Remote Similarity	NPC196485
0.67	Remote Similarity	NPC85529
0.67	Remote Similarity	NPC32006
0.6667	Remote Similarity	NPC136164
0.6667	Remote Similarity	NPC61473
0.6667	Remote Similarity	NPC189237
0.6667	Remote Similarity	NPC475022
0.6667	Remote Similarity	NPC473687
0.6667	Remote Similarity	NPC222613
0.6667	Remote Similarity	NPC470525
0.6667	Remote Similarity	NPC472684
0.6667	Remote Similarity	NPC111323
0.6667	Remote Similarity	NPC112868
0.6667	Remote Similarity	NPC168027
0.6667	Remote Similarity	NPC47937
0.6667	Remote Similarity	NPC308412
0.6667	Remote Similarity	NPC318420
0.6667	Remote Similarity	NPC245947
0.6667	Remote Similarity	NPC44963
0.6667	Remote Similarity	NPC255863
0.6667	Remote Similarity	NPC471400
0.6667	Remote Similarity	NPC134807
0.6667	Remote Similarity	NPC219498
0.6667	Remote Similarity	NPC118648
0.6667	Remote Similarity	NPC327115
0.6667	Remote Similarity	NPC225515
0.6667	Remote Similarity	NPC469646
0.6667	Remote Similarity	NPC134885
0.6667	Remote Similarity	NPC204686
0.6667	Remote Similarity	NPC185936
0.6667	Remote Similarity	NPC136150
0.6667	Remote Similarity	NPC210218
0.6667	Remote Similarity	NPC107848
0.6667	Remote Similarity	NPC326268
0.6667	Remote Similarity	NPC286229
0.6667	Remote Similarity	NPC205615

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 NPC477708 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	148
0.1-0.2	2291
0.2-0.3	4038
0.3-0.4	1989
0.4-0.5	423
0.5-0.6	214
0.6-0.7	40
0.7-0.8	5
0.8-0.85	2
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8028	Intermediate Similarity	NPD2664	Clinical (unspecified phase)
0.7945	Intermediate Similarity	NPD3704	Approved
0.7703	Intermediate Similarity	NPD6108	Clinical (unspecified phase)
0.7349	Intermediate Similarity	NPD8259	Clinical (unspecified phase)
0.7237	Intermediate Similarity	NPD7331	Phase 2
0.72	Intermediate Similarity	NPD3197	Phase 1
0.7195	Intermediate Similarity	NPD4756	Discovery
0.6744	Remote Similarity	NPD4695	Discontinued
0.6705	Remote Similarity	NPD6110	Phase 1
0.6702	Remote Similarity	NPD5282	Discontinued
0.6667	Remote Similarity	NPD7341	Phase 2
0.6622	Remote Similarity	NPD8779	Phase 3
0.6575	Remote Similarity	NPD4627	Clinical (unspecified phase)
0.6562	Remote Similarity	NPD5222	Approved
0.6562	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6562	Remote Similarity	NPD4697	Phase 3
0.6562	Remote Similarity	NPD5221	Approved
0.6556	Remote Similarity	NPD5363	Approved
0.6552	Remote Similarity	NPD5368	Approved
0.6531	Remote Similarity	NPD4696	Approved
0.6531	Remote Similarity	NPD5286	Approved
0.6531	Remote Similarity	NPD5285	Approved
0.6495	Remote Similarity	NPD5173	Approved
0.6495	Remote Similarity	NPD4755	Approved
0.6489	Remote Similarity	NPD6079	Approved
0.6484	Remote Similarity	NPD5279	Phase 3
0.6484	Remote Similarity	NPD3618	Phase 1
0.6477	Remote Similarity	NPD5369	Approved
0.6465	Remote Similarity	NPD5223	Approved
0.6452	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6452	Remote Similarity	NPD5328	Approved
0.6452	Remote Similarity	NPD6101	Approved
0.6438	Remote Similarity	NPD4266	Approved
0.6438	Remote Similarity	NPD3195	Phase 2
0.6438	Remote Similarity	NPD3194	Approved
0.6438	Remote Similarity	NPD3196	Approved
0.6404	Remote Similarity	NPD4270	Approved
0.6404	Remote Similarity	NPD6435	Approved
0.6404	Remote Similarity	NPD4269	Approved
0.64	Remote Similarity	NPD5225	Approved
0.64	Remote Similarity	NPD5226	Approved
0.64	Remote Similarity	NPD5211	Phase 2
0.64	Remote Similarity	NPD5224	Approved
0.64	Remote Similarity	NPD4633	Approved
0.6364	Remote Similarity	NPD4252	Approved
0.6364	Remote Similarity	NPD4700	Approved
0.6337	Remote Similarity	NPD5174	Approved
0.6337	Remote Similarity	NPD5175	Approved
0.6333	Remote Similarity	NPD7154	Phase 3
0.6316	Remote Similarity	NPD6411	Approved
0.6316	Remote Similarity	NPD7515	Phase 2
0.6304	Remote Similarity	NPD5786	Approved
0.6301	Remote Similarity	NPD3172	Approved
0.6296	Remote Similarity	NPD4247	Clinical (unspecified phase)
0.6289	Remote Similarity	NPD5210	Approved
0.6289	Remote Similarity	NPD4629	Approved
0.6277	Remote Similarity	NPD4753	Phase 2
0.6275	Remote Similarity	NPD5141	Approved
0.6264	Remote Similarity	NPD3666	Approved
0.6264	Remote Similarity	NPD4786	Approved
0.6264	Remote Similarity	NPD3133	Approved
0.6264	Remote Similarity	NPD3665	Phase 1
0.625	Remote Similarity	NPD6899	Approved
0.625	Remote Similarity	NPD5779	Approved
0.625	Remote Similarity	NPD6881	Approved
0.625	Remote Similarity	NPD5778	Approved
0.6226	Remote Similarity	NPD6650	Approved
0.6226	Remote Similarity	NPD6649	Approved
0.6222	Remote Similarity	NPD4800	Clinical (unspecified phase)
0.6222	Remote Similarity	NPD3667	Approved
0.6214	Remote Similarity	NPD6675	Approved
0.6214	Remote Similarity	NPD7128	Approved
0.6214	Remote Similarity	NPD5739	Approved
0.6214	Remote Similarity	NPD6402	Approved
0.6211	Remote Similarity	NPD6698	Approved
0.6211	Remote Similarity	NPD5785	Approved
0.6211	Remote Similarity	NPD46	Approved
0.6196	Remote Similarity	NPD1696	Phase 3
0.619	Remote Similarity	NPD6373	Approved
0.619	Remote Similarity	NPD6372	Approved
0.6176	Remote Similarity	NPD4754	Approved
0.6162	Remote Similarity	NPD7902	Approved
0.6154	Remote Similarity	NPD5362	Discontinued
0.6154	Remote Similarity	NPD4246	Clinical (unspecified phase)
0.6154	Remote Similarity	NPD5697	Approved
0.6136	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6136	Remote Similarity	NPD4271	Approved
0.6136	Remote Similarity	NPD4268	Approved
0.6132	Remote Similarity	NPD7102	Approved
0.6132	Remote Similarity	NPD7290	Approved
0.6132	Remote Similarity	NPD6883	Approved
0.6122	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6105	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6095	Remote Similarity	NPD4729	Approved
0.6095	Remote Similarity	NPD6011	Approved
0.6095	Remote Similarity	NPD7320	Approved
0.6095	Remote Similarity	NPD4730	Approved
0.6082	Remote Similarity	NPD4202	Approved
0.6082	Remote Similarity	NPD6399	Phase 3
0.6075	Remote Similarity	NPD6869	Approved
0.6075	Remote Similarity	NPD6847	Approved
0.6075	Remote Similarity	NPD6617	Approved
0.6075	Remote Similarity	NPD8130	Phase 1
0.6058	Remote Similarity	NPD4768	Approved
0.6058	Remote Similarity	NPD4767	Approved
0.6038	Remote Similarity	NPD6012	Approved
0.6038	Remote Similarity	NPD6014	Approved
0.6038	Remote Similarity	NPD6013	Approved
0.6027	Remote Similarity	NPD29	Approved
0.6027	Remote Similarity	NPD28	Approved
0.6022	Remote Similarity	NPD5329	Approved
0.602	Remote Similarity	NPD7748	Approved
0.6019	Remote Similarity	NPD8297	Approved
0.6019	Remote Similarity	NPD6882	Approved
0.6	Remote Similarity	NPD4821	Approved
0.6	Remote Similarity	NPD4819	Approved
0.6	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6	Remote Similarity	NPD6083	Phase 2
0.6	Remote Similarity	NPD6084	Phase 2
0.6	Remote Similarity	NPD5701	Approved
0.6	Remote Similarity	NPD4822	Approved
0.6	Remote Similarity	NPD4820	Approved
0.5981	Remote Similarity	NPD5135	Approved
0.5981	Remote Similarity	NPD5251	Approved
0.5981	Remote Similarity	NPD5247	Approved
0.5981	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.5981	Remote Similarity	NPD4634	Approved
0.5981	Remote Similarity	NPD5169	Approved
0.5981	Remote Similarity	NPD5248	Approved
0.5981	Remote Similarity	NPD5249	Phase 3
0.5981	Remote Similarity	NPD5250	Approved
0.5979	Remote Similarity	NPD7983	Approved
0.5957	Remote Similarity	NPD5690	Phase 2
0.5955	Remote Similarity	NPD3617	Approved
0.5943	Remote Similarity	NPD5128	Approved
0.5943	Remote Similarity	NPD5168	Approved
0.5926	Remote Similarity	NPD5217	Approved
0.5926	Remote Similarity	NPD5215	Approved
0.5926	Remote Similarity	NPD5216	Approved
0.5926	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.5926	Remote Similarity	NPD5127	Approved
0.5914	Remote Similarity	NPD4197	Approved
0.5859	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.5859	Remote Similarity	NPD7900	Approved
0.5833	Remote Similarity	NPD5737	Approved
0.5833	Remote Similarity	NPD6672	Approved
0.5818	Remote Similarity	NPD4632	Approved
0.5816	Remote Similarity	NPD5284	Approved
0.5816	Remote Similarity	NPD5281	Approved
0.5816	Remote Similarity	NPD4810	Clinical (unspecified phase)
0.5806	Remote Similarity	NPD5332	Approved
0.5806	Remote Similarity	NPD5331	Approved
0.58	Remote Similarity	NPD5695	Phase 3
0.5789	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.5789	Remote Similarity	NPD4694	Approved
0.5789	Remote Similarity	NPD5280	Approved
0.5789	Remote Similarity	NPD6422	Discontinued
0.5784	Remote Similarity	NPD5696	Approved
0.5773	Remote Similarity	NPD5370	Suspended
0.5766	Remote Similarity	NPD5167	Approved
0.5761	Remote Similarity	NPD4790	Discontinued
0.5753	Remote Similarity	NPD3173	Approved
0.5752	Remote Similarity	NPD6335	Approved
0.5745	Remote Similarity	NPD3668	Phase 3
0.5743	Remote Similarity	NPD7839	Suspended
0.5729	Remote Similarity	NPD4251	Approved
0.5729	Remote Similarity	NPD4250	Approved
0.5714	Remote Similarity	NPD6868	Approved
0.5702	Remote Similarity	NPD7100	Approved
0.5702	Remote Similarity	NPD7101	Approved
0.5699	Remote Similarity	NPD4223	Phase 3
0.5699	Remote Similarity	NPD4221	Approved
0.5696	Remote Similarity	NPD6109	Phase 1
0.5684	Remote Similarity	NPD1694	Approved
0.567	Remote Similarity	NPD4518	Approved
0.5664	Remote Similarity	NPD6009	Approved
0.5664	Remote Similarity	NPD6317	Approved
0.5652	Remote Similarity	NPD6054	Approved
0.5631	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.5625	Remote Similarity	NPD7521	Approved
0.5625	Remote Similarity	NPD4249	Approved
0.5625	Remote Similarity	NPD4519	Discontinued
0.5625	Remote Similarity	NPD7146	Approved
0.5625	Remote Similarity	NPD7334	Approved
0.5625	Remote Similarity	NPD4623	Approved
0.5625	Remote Similarity	NPD6409	Approved
0.5625	Remote Similarity	NPD5330	Approved
0.5625	Remote Similarity	NPD6684	Approved
0.5618	Remote Similarity	NPD8264	Approved
0.5618	Remote Similarity	NPD8039	Approved
0.5616	Remote Similarity	NPD622	Approved
0.5614	Remote Similarity	NPD6313	Approved
0.5614	Remote Similarity	NPD6314	Approved
0.5604	Remote Similarity	NPD3732	Approved
0.5603	Remote Similarity	NPD6291	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