NPASS Compound

Structure

CID38181 OpenBabel06191715372D 22 23 0 0 1 0 0 0 0 0999 V2000 1.8353 -6.6779 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9479 2.5032 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1064 -1.1691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5784 -6.0088 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3705 -5.0306 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1136 -4.3615 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9057 -3.3833 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9547 -3.0743 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7468 -2.0962 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2709 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4049 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2709 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7957 -1.7872 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5388 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4049 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5388 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5878 0.8090 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.5878 -0.8090 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.4049 2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.2788 1.7601 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.1554 -1.4781 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 1 4 1 0 0 0 0 2 20 1 0 0 0 0 3 21 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 13 1 0 0 0 0 10 11 2 0 0 0 0 10 12 1 0 0 0 0 11 14 1 0 0 0 0 12 15 2 0 0 0 0 14 16 2 0 0 0 0 14 18 1 0 0 0 0 15 16 1 0 0 0 0 15 19 1 0 0 0 0 16 17 1 0 0 0 0 17 20 1 6 0 0 0 17 22 1 0 0 0 0 18 13 1 6 0 0 0 18 21 1 0 0 0 0 18 22 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	308.2
Volume:	330.023
LogP:	4.486
LogD:	3.743
LogS:	-4.183
# Rotatable Bonds:	9
TPSA:	47.92
# H-Bond Aceptor:	4
# H-Bond Donor:	1
# Rings:	2
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.676
Synthetic Accessibility Score:	3.746
Fsp3:	0.667
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:	-4.554
MDCK Permeability:	2.465463876433205e-05
Pgp-inhibitor:	0.641
Pgp-substrate:	0.02
Human Intestinal Absorption (HIA):	0.003
20% Bioavailability (F20%):	0.005
30% Bioavailability (F30%):	0.088

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.299
Plasma Protein Binding (PPB):	95.74381256103516%
Volume Distribution (VD):	1.812
Pgp-substrate:	2.2521729469299316%

ADMET: Metabolism

CYP1A2-inhibitor:	0.066
CYP1A2-substrate:	0.955
CYP2C19-inhibitor:	0.584
CYP2C19-substrate:	0.939
CYP2C9-inhibitor:	0.446
CYP2C9-substrate:	0.823
CYP2D6-inhibitor:	0.159
CYP2D6-substrate:	0.428
CYP3A4-inhibitor:	0.4
CYP3A4-substrate:	0.551

ADMET: Excretion

Clearance (CL):	7.857
Half-life (T1/2):	0.119

ADMET: Toxicity

hERG Blockers:	0.045
Human Hepatotoxicity (H-HT):	0.062
Drug-inuced Liver Injury (DILI):	0.188
AMES Toxicity:	0.702
Rat Oral Acute Toxicity:	0.175
Maximum Recommended Daily Dose:	0.742
Skin Sensitization:	0.943
Carcinogencity:	0.319
Eye Corrosion:	0.147
Eye Irritation:	0.95
Respiratory Toxicity:	0.839

Download Data

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

Natural Product: NPC38181

Natural Product ID:	NPC38181
*Common Name:**	Paecilocin B
IUPAC Name:	(1S,3S)-1,3-dimethoxy-1-octyl-3H-2-benzofuran-4-ol
Synonyms:	Paecilocin B
Standard InCHIKey:	VKMFJAVAGSMZBP-ROUUACIJSA-N
Standard InCHI:	InChI=1S/C18H28O4/c1-4-5-6-7-8-9-13-18(21-3)14-11-10-12-15(19)16(14)17(20-2)22-18/h10-12,17,19H,4-9,13H2,1-3H3/t17-,18-/m0/s1
SMILES:	CCCCCCCC[C@]1(OC)O[C@@H](c2c1cccc2O)OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1818220
PubChem CID:	53483973
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0004191] Isocoumarans

*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
NPO30646	Paecilomyces variotii	Species	Thermoascaceae	Eukaryota	n.a.	mycelium	n.a.	PMID[21744790]

☑ 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
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	=	5.0	ug.mL-1	PMID[520787]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	=	20.0	ug.mL-1	PMID[520787]
NPT565	Organism	Vibrio parahaemolyticus	Vibrio parahaemolyticus	MIC	>	40.0	ug.mL-1	PMID[520787]

☑ 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 NPC38181 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	254
0.1-0.2	1366
0.2-0.3	3766
0.3-0.4	11318
0.4-0.5	7975
0.5-0.6	7784
0.6-0.7	7937
0.7-0.8	2253
0.8-0.85	35
0.85-0.9	4
0.9-0.95	3
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC20230
0.8534	High Similarity	NPC228452
0.8425	Intermediate Similarity	NPC325003
0.8417	Intermediate Similarity	NPC329980
0.8319	Intermediate Similarity	NPC130817
0.8306	Intermediate Similarity	NPC477152
0.8279	Intermediate Similarity	NPC328485
0.8226	Intermediate Similarity	NPC325301
0.822	Intermediate Similarity	NPC302371
0.8203	Intermediate Similarity	NPC474494
0.8203	Intermediate Similarity	NPC25729
0.819	Intermediate Similarity	NPC169450
0.8182	Intermediate Similarity	NPC475628
0.8168	Intermediate Similarity	NPC211164
0.8167	Intermediate Similarity	NPC232165
0.814	Intermediate Similarity	NPC275950
0.8103	Intermediate Similarity	NPC66834
0.8087	Intermediate Similarity	NPC471350
0.8083	Intermediate Similarity	NPC470837
0.808	Intermediate Similarity	NPC132518
0.808	Intermediate Similarity	NPC327070
0.808	Intermediate Similarity	NPC477151
0.8077	Intermediate Similarity	NPC7012
0.8077	Intermediate Similarity	NPC476345
0.8067	Intermediate Similarity	NPC26615
0.8062	Intermediate Similarity	NPC97326
0.806	Intermediate Similarity	NPC183781
0.8049	Intermediate Similarity	NPC121866
0.8049	Intermediate Similarity	NPC160235
0.8033	Intermediate Similarity	NPC476266
0.8017	Intermediate Similarity	NPC474486
0.8016	Intermediate Similarity	NPC261992
0.8	Intermediate Similarity	NPC173308
0.8	Intermediate Similarity	NPC190212
0.8	Intermediate Similarity	NPC181079
0.8	Intermediate Similarity	NPC475225
0.7984	Intermediate Similarity	NPC282255
0.7983	Intermediate Similarity	NPC275627
0.797	Intermediate Similarity	NPC101624
0.797	Intermediate Similarity	NPC184938
0.7956	Intermediate Similarity	NPC265154
0.7955	Intermediate Similarity	NPC138940
0.7955	Intermediate Similarity	NPC169973
0.7951	Intermediate Similarity	NPC123559
0.7949	Intermediate Similarity	NPC233320
0.7939	Intermediate Similarity	NPC284232
0.7937	Intermediate Similarity	NPC188997
0.7934	Intermediate Similarity	NPC41851
0.7928	Intermediate Similarity	NPC245187
0.7913	Intermediate Similarity	NPC471228
0.7913	Intermediate Similarity	NPC235762
0.7903	Intermediate Similarity	NPC151197
0.7903	Intermediate Similarity	NPC477803
0.7903	Intermediate Similarity	NPC472593
0.7899	Intermediate Similarity	NPC132720
0.7895	Intermediate Similarity	NPC248396
0.7895	Intermediate Similarity	NPC129373
0.7895	Intermediate Similarity	NPC48730
0.7895	Intermediate Similarity	NPC174911
0.7881	Intermediate Similarity	NPC241549
0.7879	Intermediate Similarity	NPC321086
0.7876	Intermediate Similarity	NPC474073
0.7876	Intermediate Similarity	NPC152097
0.7874	Intermediate Similarity	NPC249788
0.7863	Intermediate Similarity	NPC262606
0.7863	Intermediate Similarity	NPC184814
0.7852	Intermediate Similarity	NPC134260
0.7851	Intermediate Similarity	NPC176730
0.7851	Intermediate Similarity	NPC123175
0.7846	Intermediate Similarity	NPC40377
0.7846	Intermediate Similarity	NPC311293
0.7846	Intermediate Similarity	NPC148366
0.7845	Intermediate Similarity	NPC323810
0.7845	Intermediate Similarity	NPC475580
0.784	Intermediate Similarity	NPC3239
0.784	Intermediate Similarity	NPC282409
0.784	Intermediate Similarity	NPC469702
0.784	Intermediate Similarity	NPC135467
0.784	Intermediate Similarity	NPC260832
0.7836	Intermediate Similarity	NPC174191
0.7829	Intermediate Similarity	NPC43000
0.7829	Intermediate Similarity	NPC274356
0.7829	Intermediate Similarity	NPC100414
0.7823	Intermediate Similarity	NPC283616
0.7823	Intermediate Similarity	NPC63010
0.782	Intermediate Similarity	NPC24913
0.782	Intermediate Similarity	NPC112237
0.782	Intermediate Similarity	NPC177712
0.7807	Intermediate Similarity	NPC260775
0.7805	Intermediate Similarity	NPC175771
0.7805	Intermediate Similarity	NPC148055
0.7803	Intermediate Similarity	NPC473047
0.7803	Intermediate Similarity	NPC475067
0.7797	Intermediate Similarity	NPC320439
0.7795	Intermediate Similarity	NPC77789
0.7795	Intermediate Similarity	NPC18128
0.7778	Intermediate Similarity	NPC476445
0.7778	Intermediate Similarity	NPC471872
0.7778	Intermediate Similarity	NPC102639
0.7778	Intermediate Similarity	NPC100108
0.7778	Intermediate Similarity	NPC92932
0.7778	Intermediate Similarity	NPC96423
0.7778	Intermediate Similarity	NPC129176
0.7778	Intermediate Similarity	NPC47284
0.7778	Intermediate Similarity	NPC197166
0.7778	Intermediate Similarity	NPC476448
0.7778	Intermediate Similarity	NPC277798
0.7778	Intermediate Similarity	NPC154485
0.7778	Intermediate Similarity	NPC469548
0.777	Intermediate Similarity	NPC73467
0.777	Intermediate Similarity	NPC121661
0.7769	Intermediate Similarity	NPC473521
0.7769	Intermediate Similarity	NPC473221
0.7769	Intermediate Similarity	NPC257947
0.7769	Intermediate Similarity	NPC108164
0.7769	Intermediate Similarity	NPC66331
0.7769	Intermediate Similarity	NPC469386
0.7769	Intermediate Similarity	NPC98372
0.7761	Intermediate Similarity	NPC470881
0.7759	Intermediate Similarity	NPC168393
0.7759	Intermediate Similarity	NPC108497
0.7754	Intermediate Similarity	NPC230538
0.7754	Intermediate Similarity	NPC184684
0.7754	Intermediate Similarity	NPC229172
0.7754	Intermediate Similarity	NPC253878
0.7754	Intermediate Similarity	NPC103637
0.7754	Intermediate Similarity	NPC41782
0.7754	Intermediate Similarity	NPC133934
0.7754	Intermediate Similarity	NPC184641
0.7754	Intermediate Similarity	NPC36531
0.7752	Intermediate Similarity	NPC470510
0.7752	Intermediate Similarity	NPC113495
0.7752	Intermediate Similarity	NPC90318
0.7752	Intermediate Similarity	NPC33654
0.7752	Intermediate Similarity	NPC124030
0.7744	Intermediate Similarity	NPC106739
0.7744	Intermediate Similarity	NPC97316
0.7744	Intermediate Similarity	NPC227002
0.7744	Intermediate Similarity	NPC7744
0.7744	Intermediate Similarity	NPC471505
0.7742	Intermediate Similarity	NPC33270
0.7742	Intermediate Similarity	NPC69261
0.7742	Intermediate Similarity	NPC320864
0.7739	Intermediate Similarity	NPC72729
0.7739	Intermediate Similarity	NPC70677
0.7739	Intermediate Similarity	NPC12931
0.7739	Intermediate Similarity	NPC130756
0.7737	Intermediate Similarity	NPC284464
0.7734	Intermediate Similarity	NPC473451
0.7734	Intermediate Similarity	NPC248786
0.773	Intermediate Similarity	NPC116019
0.7727	Intermediate Similarity	NPC134764
0.7727	Intermediate Similarity	NPC472793
0.7727	Intermediate Similarity	NPC63574
0.7727	Intermediate Similarity	NPC171550
0.7724	Intermediate Similarity	NPC808
0.7724	Intermediate Similarity	NPC301321
0.7721	Intermediate Similarity	NPC185908
0.7719	Intermediate Similarity	NPC88420
0.7719	Intermediate Similarity	NPC79241
0.7719	Intermediate Similarity	NPC6597
0.7719	Intermediate Similarity	NPC475078
0.7717	Intermediate Similarity	NPC226712
0.7714	Intermediate Similarity	NPC180953
0.7714	Intermediate Similarity	NPC189239
0.7714	Intermediate Similarity	NPC197352
0.7714	Intermediate Similarity	NPC110763
0.7714	Intermediate Similarity	NPC166506
0.7712	Intermediate Similarity	NPC155072
0.7712	Intermediate Similarity	NPC53740
0.7712	Intermediate Similarity	NPC92623
0.7712	Intermediate Similarity	NPC67250
0.7712	Intermediate Similarity	NPC135464
0.7705	Intermediate Similarity	NPC261343
0.7704	Intermediate Similarity	NPC142547
0.7704	Intermediate Similarity	NPC135777
0.7704	Intermediate Similarity	NPC474139
0.7698	Intermediate Similarity	NPC324962
0.7698	Intermediate Similarity	NPC474808
0.7692	Intermediate Similarity	NPC325294
0.7692	Intermediate Similarity	NPC82299
0.7692	Intermediate Similarity	NPC213711
0.7692	Intermediate Similarity	NPC321822
0.7692	Intermediate Similarity	NPC40352
0.7692	Intermediate Similarity	NPC272029
0.7687	Intermediate Similarity	NPC471390
0.7687	Intermediate Similarity	NPC185777
0.7687	Intermediate Similarity	NPC58585
0.7687	Intermediate Similarity	NPC471391
0.7687	Intermediate Similarity	NPC196937
0.7687	Intermediate Similarity	NPC6836
0.7687	Intermediate Similarity	NPC215037
0.7686	Intermediate Similarity	NPC54373
0.7681	Intermediate Similarity	NPC471414
0.7681	Intermediate Similarity	NPC5155
0.7681	Intermediate Similarity	NPC472711
0.7681	Intermediate Similarity	NPC472792
0.7681	Intermediate Similarity	NPC472791
0.7681	Intermediate Similarity	NPC210192
0.768	Intermediate Similarity	NPC206205

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 NPC38181 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	224
0.1-0.2	913
0.2-0.3	1610
0.3-0.4	2789
0.4-0.5	1847
0.5-0.6	1216
0.6-0.7	495
0.7-0.8	56
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
0.7857	Intermediate Similarity	NPD3705	Approved
0.7739	Intermediate Similarity	NPD289	Clinical (unspecified phase)
0.7724	Intermediate Similarity	NPD6671	Approved
0.7717	Intermediate Similarity	NPD1091	Approved
0.7699	Intermediate Similarity	NPD844	Approved
0.7632	Intermediate Similarity	NPD288	Approved
0.7597	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7559	Intermediate Similarity	NPD4626	Approved
0.7538	Intermediate Similarity	NPD6696	Suspended
0.7521	Intermediate Similarity	NPD4750	Phase 3
0.75	Intermediate Similarity	NPD3496	Discontinued
0.7481	Intermediate Similarity	NPD4060	Phase 1
0.748	Intermediate Similarity	NPD1357	Approved
0.748	Intermediate Similarity	NPD5691	Approved
0.748	Intermediate Similarity	NPD7635	Approved
0.744	Intermediate Similarity	NPD709	Approved
0.7422	Intermediate Similarity	NPD5126	Approved
0.7422	Intermediate Similarity	NPD5125	Phase 3
0.7391	Intermediate Similarity	NPD4108	Discontinued
0.7388	Intermediate Similarity	NPD4625	Phase 3
0.7373	Intermediate Similarity	NPD846	Approved
0.7373	Intermediate Similarity	NPD940	Approved
0.7368	Intermediate Similarity	NPD1712	Approved
0.7368	Intermediate Similarity	NPD845	Approved
0.7368	Intermediate Similarity	NPD2861	Phase 2
0.735	Intermediate Similarity	NPD3020	Approved
0.7339	Intermediate Similarity	NPD1138	Approved
0.7328	Intermediate Similarity	NPD4749	Approved
0.7319	Intermediate Similarity	NPD4978	Clinical (unspecified phase)
0.7313	Intermediate Similarity	NPD4908	Phase 1
0.7304	Intermediate Similarity	NPD1432	Clinical (unspecified phase)
0.7293	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7266	Intermediate Similarity	NPD3091	Approved
0.7258	Intermediate Similarity	NPD1139	Approved
0.7258	Intermediate Similarity	NPD1137	Approved
0.7252	Intermediate Similarity	NPD2233	Approved
0.7252	Intermediate Similarity	NPD2230	Approved
0.7252	Intermediate Similarity	NPD2232	Approved
0.7241	Intermediate Similarity	NPD2859	Approved
0.7241	Intermediate Similarity	NPD2860	Approved
0.7236	Intermediate Similarity	NPD3021	Approved
0.7236	Intermediate Similarity	NPD3022	Approved
0.7218	Intermediate Similarity	NPD3094	Phase 2
0.7213	Intermediate Similarity	NPD2342	Discontinued
0.7213	Intermediate Similarity	NPD290	Approved
0.7206	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7206	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7183	Intermediate Similarity	NPD6674	Discontinued
0.7176	Intermediate Similarity	NPD1610	Phase 2
0.7165	Intermediate Similarity	NPD7157	Approved
0.7163	Intermediate Similarity	NPD7266	Discontinued
0.7155	Intermediate Similarity	NPD2934	Approved
0.7155	Intermediate Similarity	NPD2933	Approved
0.7154	Intermediate Similarity	NPD2684	Approved
0.7143	Intermediate Similarity	NPD1398	Phase 1
0.7132	Intermediate Similarity	NPD3027	Phase 3
0.7131	Intermediate Similarity	NPD968	Approved
0.7122	Intermediate Similarity	NPD4097	Suspended
0.7122	Intermediate Similarity	NPD2157	Approved
0.712	Intermediate Similarity	NPD969	Suspended
0.712	Intermediate Similarity	NPD228	Approved
0.7111	Intermediate Similarity	NPD5736	Approved
0.7109	Intermediate Similarity	NPD7340	Approved
0.7094	Intermediate Similarity	NPD1809	Phase 2
0.7067	Intermediate Similarity	NPD37	Approved
0.7063	Intermediate Similarity	NPD7843	Approved
0.7059	Intermediate Similarity	NPD6234	Discontinued
0.7045	Intermediate Similarity	NPD1611	Approved
0.7045	Intermediate Similarity	NPD3092	Approved
0.7042	Intermediate Similarity	NPD5762	Approved
0.7042	Intermediate Similarity	NPD5763	Approved
0.7039	Intermediate Similarity	NPD4965	Approved
0.7039	Intermediate Similarity	NPD4966	Approved
0.7039	Intermediate Similarity	NPD4967	Phase 2
0.7023	Intermediate Similarity	NPD3095	Discontinued
0.7023	Intermediate Similarity	NPD1778	Approved
0.7008	Intermediate Similarity	NPD5283	Phase 1
0.7	Intermediate Similarity	NPD6653	Approved
0.7	Intermediate Similarity	NPD1548	Phase 1
0.6992	Remote Similarity	NPD1444	Approved
0.6992	Remote Similarity	NPD1445	Approved
0.6984	Remote Similarity	NPD6124	Clinical (unspecified phase)
0.6978	Remote Similarity	NPD1612	Clinical (unspecified phase)
0.6978	Remote Similarity	NPD2238	Phase 2
0.6978	Remote Similarity	NPD4140	Approved
0.6978	Remote Similarity	NPD1613	Approved
0.6977	Remote Similarity	NPD9493	Approved
0.6972	Remote Similarity	NPD2935	Discontinued
0.6963	Remote Similarity	NPD2797	Approved
0.696	Remote Similarity	NPD1792	Phase 2
0.6947	Remote Similarity	NPD3443	Approved
0.6947	Remote Similarity	NPD3444	Approved
0.6947	Remote Similarity	NPD3445	Approved
0.6944	Remote Similarity	NPD5698	Clinical (unspecified phase)
0.694	Remote Similarity	NPD3685	Discontinued
0.694	Remote Similarity	NPD5327	Phase 3
0.6939	Remote Similarity	NPD2532	Approved
0.6939	Remote Similarity	NPD2534	Approved
0.6939	Remote Similarity	NPD2533	Approved
0.6934	Remote Similarity	NPD1529	Clinical (unspecified phase)
0.6934	Remote Similarity	NPD596	Approved
0.6934	Remote Similarity	NPD600	Approved
0.6923	Remote Similarity	NPD6005	Phase 3
0.6923	Remote Similarity	NPD6002	Phase 3
0.6923	Remote Similarity	NPD6004	Phase 3
0.6923	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD2029	Clinical (unspecified phase)
0.6912	Remote Similarity	NPD558	Phase 2
0.6912	Remote Similarity	NPD4624	Approved
0.6912	Remote Similarity	NPD6584	Phase 3
0.6906	Remote Similarity	NPD6663	Approved
0.6906	Remote Similarity	NPD840	Approved
0.6906	Remote Similarity	NPD839	Approved
0.6899	Remote Similarity	NPD6387	Discontinued
0.6897	Remote Similarity	NPD3892	Phase 2
0.6894	Remote Similarity	NPD3019	Approved
0.6894	Remote Similarity	NPD2932	Approved
0.6894	Remote Similarity	NPD4059	Approved
0.6875	Remote Similarity	NPD7159	Clinical (unspecified phase)
0.687	Remote Similarity	NPD2226	Clinical (unspecified phase)
0.6866	Remote Similarity	NPD2231	Phase 2
0.6866	Remote Similarity	NPD2235	Phase 2
0.6866	Remote Similarity	NPD1840	Phase 2
0.6861	Remote Similarity	NPD1530	Clinical (unspecified phase)
0.686	Remote Similarity	NPD1242	Phase 1
0.6859	Remote Similarity	NPD7199	Phase 2
0.6857	Remote Similarity	NPD3620	Phase 2
0.6857	Remote Similarity	NPD3619	Clinical (unspecified phase)
0.6857	Remote Similarity	NPD2203	Discontinued
0.6855	Remote Similarity	NPD7228	Approved
0.6838	Remote Similarity	NPD4339	Clinical (unspecified phase)
0.6835	Remote Similarity	NPD3268	Approved
0.6835	Remote Similarity	NPD1699	Clinical (unspecified phase)
0.6835	Remote Similarity	NPD3764	Approved
0.6822	Remote Similarity	NPD497	Approved
0.6818	Remote Similarity	NPD5585	Approved
0.6814	Remote Similarity	NPD111	Approved
0.6809	Remote Similarity	NPD6355	Discontinued
0.6809	Remote Similarity	NPD5735	Approved
0.68	Remote Similarity	NPD1653	Approved
0.6797	Remote Similarity	NPD821	Approved
0.6791	Remote Similarity	NPD422	Phase 1
0.6788	Remote Similarity	NPD3690	Phase 2
0.6788	Remote Similarity	NPD3691	Phase 2
0.6783	Remote Similarity	NPD1753	Discontinued
0.6772	Remote Similarity	NPD7184	Clinical (unspecified phase)
0.6765	Remote Similarity	NPD1283	Approved
0.6763	Remote Similarity	NPD5952	Clinical (unspecified phase)
0.6761	Remote Similarity	NPD6353	Approved
0.6759	Remote Similarity	NPD7037	Approved
0.6759	Remote Similarity	NPD970	Clinical (unspecified phase)
0.6757	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6757	Remote Similarity	NPD7040	Clinical (unspecified phase)
0.6757	Remote Similarity	NPD7041	Phase 2
0.6744	Remote Similarity	NPD498	Approved
0.6744	Remote Similarity	NPD496	Approved
0.6744	Remote Similarity	NPD495	Approved
0.6742	Remote Similarity	NPD7741	Discontinued
0.6739	Remote Similarity	NPD2237	Approved
0.6738	Remote Similarity	NPD2979	Phase 3
0.6736	Remote Similarity	NPD6100	Approved
0.6736	Remote Similarity	NPD6099	Approved
0.6736	Remote Similarity	NPD6032	Approved
0.672	Remote Similarity	NPD3134	Approved
0.6718	Remote Similarity	NPD7325	Clinical (unspecified phase)
0.6715	Remote Similarity	NPD6362	Approved
0.6714	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6711	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6694	Remote Similarity	NPD9273	Approved
0.6692	Remote Similarity	NPD4093	Discontinued
0.6692	Remote Similarity	NPD1651	Approved
0.6692	Remote Similarity	NPD9618	Approved
0.6692	Remote Similarity	NPD9614	Approved
0.6691	Remote Similarity	NPD6583	Phase 3
0.6691	Remote Similarity	NPD1669	Approved
0.6691	Remote Similarity	NPD6582	Phase 2
0.669	Remote Similarity	NPD1375	Discontinued
0.6689	Remote Similarity	NPD5058	Phase 3
0.6667	Remote Similarity	NPD1358	Approved
0.6667	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD5535	Approved
0.6667	Remote Similarity	NPD5350	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD5351	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6090	Discontinued
0.6667	Remote Similarity	NPD776	Approved
0.6667	Remote Similarity	NPD7033	Discontinued
0.6667	Remote Similarity	NPD2798	Approved
0.6667	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6646	Remote Similarity	NPD3818	Discontinued
0.6645	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6644	Remote Similarity	NPD6087	Phase 1
0.6644	Remote Similarity	NPD2424	Discontinued
0.6643	Remote Similarity	NPD7095	Approved
0.6642	Remote Similarity	NPD2667	Approved
0.6642	Remote Similarity	NPD8651	Approved
0.6642	Remote Similarity	NPD2668	Approved
0.6641	Remote Similarity	NPD2181	Clinical (unspecified phase)
0.6641	Remote Similarity	NPD2557	Approved
0.6622	Remote Similarity	NPD3692	Discontinued

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