NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	246.13
Volume:	269.992
LogP:	4.061
LogD:	3.807
LogS:	-3.839
# Rotatable Bonds:	5
TPSA:	46.53
# H-Bond Aceptor:	3
# H-Bond Donor:	1
# Rings:	1
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.504
Synthetic Accessibility Score:	2.384
Fsp3:	0.267
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.618
MDCK Permeability:	2.7332471290719695e-05
Pgp-inhibitor:	0.109
Pgp-substrate:	0.019
Human Intestinal Absorption (HIA):	0.024
20% Bioavailability (F20%):	0.013
30% Bioavailability (F30%):	0.139

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.697
Plasma Protein Binding (PPB):	97.88153839111328%
Volume Distribution (VD):	2.036
Pgp-substrate:	3.8326966762542725%

ADMET: Metabolism

CYP1A2-inhibitor:	0.976
CYP1A2-substrate:	0.661
CYP2C19-inhibitor:	0.918
CYP2C19-substrate:	0.386
CYP2C9-inhibitor:	0.806
CYP2C9-substrate:	0.932
CYP2D6-inhibitor:	0.585
CYP2D6-substrate:	0.837
CYP3A4-inhibitor:	0.323
CYP3A4-substrate:	0.243

ADMET: Excretion

Clearance (CL):	14.788
Half-life (T1/2):	0.849

ADMET: Toxicity

hERG Blockers:	0.066
Human Hepatotoxicity (H-HT):	0.736
Drug-inuced Liver Injury (DILI):	0.063
AMES Toxicity:	0.146
Rat Oral Acute Toxicity:	0.168
Maximum Recommended Daily Dose:	0.736
Skin Sensitization:	0.877
Carcinogencity:	0.192
Eye Corrosion:	0.006
Eye Irritation:	0.098
Respiratory Toxicity:	0.704

Download Data

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

Natural Product: NPC471954

Natural Product ID:	NPC471954
*Common Name:**	LZEOAWXRNGQEHO-TWGQIWQCSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	LZEOAWXRNGQEHO-TWGQIWQCSA-N
Standard InCHI:	InChI=1S/C15H18O3/c1-11(2)4-7-13-10-12(5-8-14(13)16)6-9-15(17)18-3/h4-6,8-10,16H,7H2,1-3H3/b9-6-
SMILES:	CC(=CCC1=C(C=CC(=C1)C=CC(=O)OC)O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3310872
PubChem CID:	n.a.
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000476] Cinnamic acids and derivatives [CHEMONTID:0001391] Hydroxycinnamic acids and derivatives [CHEMONTID:0003002] Hydroxycinnamic acid esters [CHEMONTID:0000465] Coumaric acid esters

*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
NPO32782	ducrosia ismaelis	Species	Apiaceae	Eukaryota	aerial parts	n.a.	n.a.	PMID[24953601]

☑ 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
Cell Line	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT113	Cell Line	RAW264.7	Mus musculus	Activity	=	85.05	%	PMID[482528]

☑ 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 NPC471954 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	207
0.1-0.2	1371
0.2-0.3	3808
0.3-0.4	10422
0.4-0.5	8550
0.5-0.6	7667
0.6-0.7	8532
0.7-0.8	1976
0.8-0.85	129
0.85-0.9	23
0.9-0.95	9
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC75272
0.9604	High Similarity	NPC303141
0.9412	High Similarity	NPC243677
0.9406	High Similarity	NPC470202
0.934	High Similarity	NPC199462
0.9208	High Similarity	NPC253746
0.9143	High Similarity	NPC470039
0.9029	High Similarity	NPC304638
0.8972	High Similarity	NPC473809
0.8889	High Similarity	NPC139946
0.8818	High Similarity	NPC41851
0.8812	High Similarity	NPC246679
0.8796	High Similarity	NPC183700
0.8783	High Similarity	NPC67300
0.875	High Similarity	NPC94343
0.8738	High Similarity	NPC128723
0.8738	High Similarity	NPC171843
0.8713	High Similarity	NPC81010
0.8713	High Similarity	NPC32977
0.8692	High Similarity	NPC260952
0.8679	High Similarity	NPC227255
0.8679	High Similarity	NPC127676
0.8632	High Similarity	NPC184219
0.8611	High Similarity	NPC206341
0.8585	High Similarity	NPC2518
0.8584	High Similarity	NPC183154
0.8584	High Similarity	NPC122117
0.8584	High Similarity	NPC263754
0.8515	High Similarity	NPC204210
0.8509	High Similarity	NPC161943
0.8509	High Similarity	NPC273282
0.8509	High Similarity	NPC474890
0.8468	Intermediate Similarity	NPC26615
0.8468	Intermediate Similarity	NPC228988
0.8462	Intermediate Similarity	NPC77492
0.8448	Intermediate Similarity	NPC131868
0.8447	Intermediate Similarity	NPC8392
0.8431	Intermediate Similarity	NPC181709
0.8393	Intermediate Similarity	NPC242136
0.8393	Intermediate Similarity	NPC190212
0.8381	Intermediate Similarity	NPC122005
0.8381	Intermediate Similarity	NPC252821
0.8378	Intermediate Similarity	NPC226250
0.8376	Intermediate Similarity	NPC251259
0.8365	Intermediate Similarity	NPC283711
0.8364	Intermediate Similarity	NPC79543
0.8349	Intermediate Similarity	NPC228737
0.8348	Intermediate Similarity	NPC203124
0.8348	Intermediate Similarity	NPC309434
0.8347	Intermediate Similarity	NPC473744
0.8333	Intermediate Similarity	NPC83718
0.8319	Intermediate Similarity	NPC33749
0.8319	Intermediate Similarity	NPC114918
0.8319	Intermediate Similarity	NPC328593
0.8319	Intermediate Similarity	NPC261453
0.8319	Intermediate Similarity	NPC265413
0.8319	Intermediate Similarity	NPC10154
0.8317	Intermediate Similarity	NPC318325
0.8317	Intermediate Similarity	NPC123273
0.8317	Intermediate Similarity	NPC70436
0.8317	Intermediate Similarity	NPC242240
0.8304	Intermediate Similarity	NPC17693
0.8302	Intermediate Similarity	NPC225506
0.8288	Intermediate Similarity	NPC63345
0.8273	Intermediate Similarity	NPC31274
0.8269	Intermediate Similarity	NPC286006
0.8269	Intermediate Similarity	NPC257182
0.8269	Intermediate Similarity	NPC144682
0.8264	Intermediate Similarity	NPC243688
0.825	Intermediate Similarity	NPC244495
0.825	Intermediate Similarity	NPC93219
0.8246	Intermediate Similarity	NPC474967
0.8246	Intermediate Similarity	NPC296526
0.8246	Intermediate Similarity	NPC233669
0.8241	Intermediate Similarity	NPC93831
0.823	Intermediate Similarity	NPC35344
0.823	Intermediate Similarity	NPC95381
0.823	Intermediate Similarity	NPC141003
0.8218	Intermediate Similarity	NPC113460
0.8218	Intermediate Similarity	NPC25493
0.8214	Intermediate Similarity	NPC470355
0.8214	Intermediate Similarity	NPC228609
0.8208	Intermediate Similarity	NPC245561
0.8197	Intermediate Similarity	NPC217431
0.8197	Intermediate Similarity	NPC478215
0.8174	Intermediate Similarity	NPC131192
0.8174	Intermediate Similarity	NPC128825
0.8174	Intermediate Similarity	NPC281277
0.8173	Intermediate Similarity	NPC289769
0.8173	Intermediate Similarity	NPC128062
0.8167	Intermediate Similarity	NPC89630
0.8167	Intermediate Similarity	NPC474532
0.8165	Intermediate Similarity	NPC138942
0.8165	Intermediate Similarity	NPC288760
0.8165	Intermediate Similarity	NPC154899
0.8165	Intermediate Similarity	NPC233396
0.8158	Intermediate Similarity	NPC197513
0.8151	Intermediate Similarity	NPC325301
0.8151	Intermediate Similarity	NPC327070
0.8148	Intermediate Similarity	NPC179686
0.8148	Intermediate Similarity	NPC168829
0.8148	Intermediate Similarity	NPC135784
0.8145	Intermediate Similarity	NPC473777
0.8137	Intermediate Similarity	NPC177420
0.8137	Intermediate Similarity	NPC280347
0.8137	Intermediate Similarity	NPC258219
0.8136	Intermediate Similarity	NPC470848
0.8136	Intermediate Similarity	NPC470849
0.8131	Intermediate Similarity	NPC52472
0.812	Intermediate Similarity	NPC263386
0.812	Intermediate Similarity	NPC141791
0.812	Intermediate Similarity	NPC328459
0.812	Intermediate Similarity	NPC90522
0.812	Intermediate Similarity	NPC473767
0.8119	Intermediate Similarity	NPC23167
0.8119	Intermediate Similarity	NPC407
0.8119	Intermediate Similarity	NPC307235
0.8115	Intermediate Similarity	NPC473993
0.8115	Intermediate Similarity	NPC121104
0.8113	Intermediate Similarity	NPC201967
0.8113	Intermediate Similarity	NPC140619
0.8108	Intermediate Similarity	NPC68260
0.8108	Intermediate Similarity	NPC279887
0.8099	Intermediate Similarity	NPC137416
0.8095	Intermediate Similarity	NPC26244
0.8091	Intermediate Similarity	NPC113457
0.8091	Intermediate Similarity	NPC92623
0.8091	Intermediate Similarity	NPC326447
0.8091	Intermediate Similarity	NPC176971
0.8091	Intermediate Similarity	NPC135464
0.8083	Intermediate Similarity	NPC174991
0.808	Intermediate Similarity	NPC302844
0.8077	Intermediate Similarity	NPC138117
0.8077	Intermediate Similarity	NPC325292
0.8073	Intermediate Similarity	NPC288411
0.807	Intermediate Similarity	NPC211421
0.8058	Intermediate Similarity	NPC55561
0.8058	Intermediate Similarity	NPC300017
0.8056	Intermediate Similarity	NPC472585
0.8051	Intermediate Similarity	NPC478121
0.8051	Intermediate Similarity	NPC72977
0.8049	Intermediate Similarity	NPC185066
0.8037	Intermediate Similarity	NPC130193
0.8036	Intermediate Similarity	NPC95172
0.8036	Intermediate Similarity	NPC282855
0.8036	Intermediate Similarity	NPC234639
0.8036	Intermediate Similarity	NPC98392
0.8036	Intermediate Similarity	NPC26013
0.8034	Intermediate Similarity	NPC94298
0.8034	Intermediate Similarity	NPC27633
0.8034	Intermediate Similarity	NPC94637
0.802	Intermediate Similarity	NPC155393
0.802	Intermediate Similarity	NPC197783
0.8019	Intermediate Similarity	NPC473388
0.8018	Intermediate Similarity	NPC157473
0.8018	Intermediate Similarity	NPC151530
0.8017	Intermediate Similarity	NPC19290
0.8017	Intermediate Similarity	NPC128249
0.8017	Intermediate Similarity	NPC471936
0.8	Intermediate Similarity	NPC121168
0.8	Intermediate Similarity	NPC477151
0.8	Intermediate Similarity	NPC316301
0.8	Intermediate Similarity	NPC151715
0.8	Intermediate Similarity	NPC128730
0.8	Intermediate Similarity	NPC27323
0.8	Intermediate Similarity	NPC132518
0.8	Intermediate Similarity	NPC81808
0.8	Intermediate Similarity	NPC217472
0.8	Intermediate Similarity	NPC473855
0.8	Intermediate Similarity	NPC96286
0.8	Intermediate Similarity	NPC248429
0.8	Intermediate Similarity	NPC475192
0.8	Intermediate Similarity	NPC152415
0.7984	Intermediate Similarity	NPC86257
0.7984	Intermediate Similarity	NPC288290
0.7982	Intermediate Similarity	NPC108497
0.7982	Intermediate Similarity	NPC13426
0.7981	Intermediate Similarity	NPC45040
0.7981	Intermediate Similarity	NPC306074
0.7981	Intermediate Similarity	NPC304541
0.7965	Intermediate Similarity	NPC208229
0.7949	Intermediate Similarity	NPC174087
0.7949	Intermediate Similarity	NPC65791
0.7949	Intermediate Similarity	NPC160199
0.7946	Intermediate Similarity	NPC63698
0.7946	Intermediate Similarity	NPC262365
0.7946	Intermediate Similarity	NPC61885
0.7946	Intermediate Similarity	NPC75440
0.7944	Intermediate Similarity	NPC260000
0.7944	Intermediate Similarity	NPC175298
0.7941	Intermediate Similarity	NPC184169
0.7937	Intermediate Similarity	NPC173034
0.7937	Intermediate Similarity	NPC194277
0.7934	Intermediate Similarity	NPC14141
0.7934	Intermediate Similarity	NPC477152
0.7934	Intermediate Similarity	NPC472518
0.7931	Intermediate Similarity	NPC23402
0.7928	Intermediate Similarity	NPC69332
0.7928	Intermediate Similarity	NPC271274
0.7928	Intermediate Similarity	NPC1786

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 NPC471954 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	193
0.1-0.2	960
0.2-0.3	1368
0.3-0.4	2644
0.4-0.5	2049
0.5-0.6	1245
0.6-0.7	603
0.7-0.8	80
0.8-0.85	7
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8522	High Similarity	NPD4626	Approved
0.8269	Intermediate Similarity	NPD1809	Phase 2
0.8252	Intermediate Similarity	NPD845	Approved
0.8174	Intermediate Similarity	NPD9493	Approved
0.812	Intermediate Similarity	NPD5691	Approved
0.8095	Intermediate Similarity	NPD2859	Approved
0.8095	Intermediate Similarity	NPD2860	Approved
0.8091	Intermediate Similarity	NPD3134	Approved
0.8056	Intermediate Similarity	NPD940	Approved
0.8056	Intermediate Similarity	NPD846	Approved
0.8034	Intermediate Similarity	NPD9545	Approved
0.8018	Intermediate Similarity	NPD1358	Approved
0.8	Intermediate Similarity	NPD2934	Approved
0.8	Intermediate Similarity	NPD1432	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD2933	Approved
0.7925	Intermediate Similarity	NPD844	Approved
0.7917	Intermediate Similarity	NPD422	Phase 1
0.787	Intermediate Similarity	NPD3020	Approved
0.7822	Intermediate Similarity	NPD111	Approved
0.7769	Intermediate Similarity	NPD2935	Discontinued
0.7699	Intermediate Similarity	NPD9265	Clinical (unspecified phase)
0.7686	Intermediate Similarity	NPD3496	Discontinued
0.7685	Intermediate Similarity	NPD288	Approved
0.7679	Intermediate Similarity	NPD9697	Approved
0.7667	Intermediate Similarity	NPD4196	Clinical (unspecified phase)
0.7661	Intermediate Similarity	NPD1164	Approved
0.7656	Intermediate Similarity	NPD4060	Phase 1
0.7636	Intermediate Similarity	NPD289	Clinical (unspecified phase)
0.7632	Intermediate Similarity	NPD74	Approved
0.7632	Intermediate Similarity	NPD9266	Approved
0.7586	Intermediate Similarity	NPD6124	Clinical (unspecified phase)
0.7544	Intermediate Similarity	NPD9267	Approved
0.7544	Intermediate Similarity	NPD9263	Approved
0.7544	Intermediate Similarity	NPD9264	Approved
0.7541	Intermediate Similarity	NPD3847	Discontinued
0.7521	Intermediate Similarity	NPD5535	Approved
0.752	Intermediate Similarity	NPD2797	Approved
0.75	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7479	Intermediate Similarity	NPD256	Approved
0.7479	Intermediate Similarity	NPD255	Approved
0.7478	Intermediate Similarity	NPD2684	Approved
0.7463	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7458	Intermediate Similarity	NPD7159	Clinical (unspecified phase)
0.744	Intermediate Similarity	NPD1283	Approved
0.7436	Intermediate Similarity	NPD228	Approved
0.7424	Intermediate Similarity	NPD2799	Discontinued
0.7419	Intermediate Similarity	NPD9717	Approved
0.7407	Intermediate Similarity	NPD7003	Approved
0.7373	Intermediate Similarity	NPD1138	Approved
0.7333	Intermediate Similarity	NPD6671	Approved
0.7328	Intermediate Similarity	NPD5124	Phase 1
0.7328	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7317	Intermediate Similarity	NPD1778	Approved
0.7311	Intermediate Similarity	NPD1241	Discontinued
0.7288	Intermediate Similarity	NPD1137	Approved
0.7288	Intermediate Similarity	NPD1139	Approved
0.7266	Intermediate Similarity	NPD5736	Approved
0.7266	Intermediate Similarity	NPD4208	Discontinued
0.7265	Intermediate Similarity	NPD3022	Approved
0.7265	Intermediate Similarity	NPD3021	Approved
0.7252	Intermediate Similarity	NPD1240	Approved
0.7244	Intermediate Similarity	NPD1203	Approved
0.7241	Intermediate Similarity	NPD290	Approved
0.7231	Intermediate Similarity	NPD3268	Approved
0.7231	Intermediate Similarity	NPD3764	Approved
0.7231	Intermediate Similarity	NPD6798	Discontinued
0.7227	Intermediate Similarity	NPD7635	Approved
0.7227	Intermediate Similarity	NPD821	Approved
0.7227	Intermediate Similarity	NPD7843	Approved
0.7222	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7209	Intermediate Similarity	NPD4207	Discontinued
0.72	Intermediate Similarity	NPD1535	Discovery
0.72	Intermediate Similarity	NPD1281	Approved
0.7193	Intermediate Similarity	NPD9261	Approved
0.7179	Intermediate Similarity	NPD6831	Clinical (unspecified phase)
0.7155	Intermediate Similarity	NPD968	Approved
0.7154	Intermediate Similarity	NPD5304	Approved
0.7154	Intermediate Similarity	NPD1548	Phase 1
0.7154	Intermediate Similarity	NPD1759	Phase 1
0.7154	Intermediate Similarity	NPD5303	Approved
0.7154	Intermediate Similarity	NPD1894	Discontinued
0.7153	Intermediate Similarity	NPD8166	Discontinued
0.7143	Intermediate Similarity	NPD1481	Phase 2
0.7143	Intermediate Similarity	NPD1607	Approved
0.7132	Intermediate Similarity	NPD4212	Discontinued
0.7131	Intermediate Similarity	NPD9568	Approved
0.713	Intermediate Similarity	NPD9608	Approved
0.713	Intermediate Similarity	NPD9610	Approved
0.7119	Intermediate Similarity	NPD4750	Phase 3
0.7119	Intermediate Similarity	NPD5451	Approved
0.7111	Intermediate Similarity	NPD4476	Approved
0.7111	Intermediate Similarity	NPD4477	Approved
0.7107	Intermediate Similarity	NPD9281	Approved
0.7099	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7099	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7099	Intermediate Similarity	NPD2313	Discontinued
0.7097	Intermediate Similarity	NPD1651	Approved
0.7094	Intermediate Similarity	NPD2342	Discontinued
0.7073	Intermediate Similarity	NPD1758	Phase 1
0.7068	Intermediate Similarity	NPD6355	Discontinued
0.7063	Intermediate Similarity	NPD1611	Approved
0.7063	Intermediate Similarity	NPD1610	Phase 2
0.7059	Intermediate Similarity	NPD7266	Discontinued
0.7054	Intermediate Similarity	NPD3691	Phase 2
0.7054	Intermediate Similarity	NPD3690	Phase 2
0.7054	Intermediate Similarity	NPD2798	Approved
0.7049	Intermediate Similarity	NPD7157	Approved
0.7045	Intermediate Similarity	NPD6663	Approved
0.704	Intermediate Similarity	NPD3019	Approved
0.704	Intermediate Similarity	NPD2932	Approved
0.704	Intermediate Similarity	NPD4589	Approved
0.7031	Intermediate Similarity	NPD3225	Approved
0.7025	Intermediate Similarity	NPD2234	Approved
0.7025	Intermediate Similarity	NPD2229	Approved
0.7025	Intermediate Similarity	NPD2228	Approved
0.7018	Intermediate Similarity	NPD3028	Approved
0.7018	Intermediate Similarity	NPD1242	Phase 1
0.7016	Intermediate Similarity	NPD3091	Approved
0.7009	Intermediate Similarity	NPD1444	Approved
0.7009	Intermediate Similarity	NPD1445	Approved
0.7008	Intermediate Similarity	NPD3972	Approved
0.6993	Remote Similarity	NPD7458	Discontinued
0.6992	Remote Similarity	NPD4140	Approved
0.6992	Remote Similarity	NPD405	Clinical (unspecified phase)
0.6992	Remote Similarity	NPD2203	Discontinued
0.6991	Remote Similarity	NPD9273	Approved
0.6985	Remote Similarity	NPD5404	Approved
0.6985	Remote Similarity	NPD5405	Approved
0.6985	Remote Similarity	NPD5406	Approved
0.6985	Remote Similarity	NPD5408	Approved
0.6983	Remote Similarity	NPD5909	Discontinued
0.6981	Remote Similarity	NPD5734	Clinical (unspecified phase)
0.6977	Remote Similarity	NPD1131	Approved
0.6977	Remote Similarity	NPD1134	Approved
0.6977	Remote Similarity	NPD1129	Approved
0.6977	Remote Similarity	NPD1135	Approved
0.6977	Remote Similarity	NPD1133	Approved
0.6977	Remote Similarity	NPD987	Approved
0.6975	Remote Similarity	NPD9380	Clinical (unspecified phase)
0.6972	Remote Similarity	NPD9258	Approved
0.6972	Remote Similarity	NPD9256	Approved
0.6967	Remote Similarity	NPD690	Clinical (unspecified phase)
0.6963	Remote Similarity	NPD7097	Phase 1
0.696	Remote Similarity	NPD4235	Clinical (unspecified phase)
0.6953	Remote Similarity	NPD6583	Phase 3
0.6953	Remote Similarity	NPD6582	Phase 2
0.6947	Remote Similarity	NPD6832	Phase 2
0.6947	Remote Similarity	NPD4908	Phase 1
0.694	Remote Similarity	NPD230	Phase 1
0.6935	Remote Similarity	NPD5536	Phase 2
0.6934	Remote Similarity	NPD2343	Clinical (unspecified phase)
0.6929	Remote Similarity	NPD1201	Approved
0.6929	Remote Similarity	NPD6666	Approved
0.6929	Remote Similarity	NPD6667	Approved
0.6917	Remote Similarity	NPD4248	Discontinued
0.6917	Remote Similarity	NPD2181	Clinical (unspecified phase)
0.6912	Remote Similarity	NPD4308	Phase 3
0.6912	Remote Similarity	NPD1510	Phase 2
0.6911	Remote Similarity	NPD6387	Discontinued
0.6906	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6906	Remote Similarity	NPD4628	Phase 3
0.6906	Remote Similarity	NPD3750	Approved
0.6905	Remote Similarity	NPD2667	Approved
0.6905	Remote Similarity	NPD2668	Approved
0.6899	Remote Similarity	NPD196	Phase 1
0.6897	Remote Similarity	NPD6647	Phase 2
0.6897	Remote Similarity	NPD7411	Suspended
0.6897	Remote Similarity	NPD9500	Approved
0.6894	Remote Similarity	NPD7095	Approved
0.6894	Remote Similarity	NPD5163	Phase 2
0.6885	Remote Similarity	NPD5283	Phase 1
0.6884	Remote Similarity	NPD2424	Discontinued
0.6884	Remote Similarity	NPD970	Clinical (unspecified phase)
0.6881	Remote Similarity	NPD9295	Approved
0.6875	Remote Similarity	NPD1608	Approved
0.687	Remote Similarity	NPD2861	Phase 2
0.687	Remote Similarity	NPD9494	Approved
0.6866	Remote Similarity	NPD825	Approved
0.6866	Remote Similarity	NPD826	Approved
0.6855	Remote Similarity	NPD694	Clinical (unspecified phase)
0.6852	Remote Similarity	NPD1282	Approved
0.685	Remote Similarity	NPD3143	Discontinued
0.6846	Remote Similarity	NPD3266	Approved
0.6846	Remote Similarity	NPD1470	Approved
0.6846	Remote Similarity	NPD3267	Approved
0.6842	Remote Similarity	NPD1048	Approved
0.6842	Remote Similarity	NPD9495	Approved
0.6842	Remote Similarity	NPD411	Approved
0.6838	Remote Similarity	NPD4978	Clinical (unspecified phase)
0.6838	Remote Similarity	NPD164	Approved
0.6835	Remote Similarity	NPD1652	Phase 2
0.6833	Remote Similarity	NPD1792	Phase 2
0.6832	Remote Similarity	NPD9716	Approved
0.6831	Remote Similarity	NPD4378	Clinical (unspecified phase)
0.6829	Remote Similarity	NPD5951	Approved
0.6825	Remote Similarity	NPD1357	Approved
0.6824	Remote Similarity	NPD7768	Phase 2
0.6822	Remote Similarity	NPD1669	Approved
0.6822	Remote Similarity	NPD3685	Discontinued
0.6818	Remote Similarity	NPD1008	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