NPASS Compound

Structure

NPC204884 OpenBabel07101719242D 25 28 0 0 1 0 0 0 0 0999 V2000 -2.5454 -1.2396 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2495 -2.2890 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0861 -2.7354 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6585 -0.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0485 -1.3105 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2147 -1.7919 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7154 -1.6069 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0352 -1.3458 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0146 1.0752 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5945 -1.3902 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2147 0.1335 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0485 -0.3478 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.9887 -0.6421 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.3810 -0.3478 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1772 0.0617 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.5662 0.4585 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6656 0.2963 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.3810 -1.3105 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.2611 -0.6802 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.8822 0.1335 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.0760 0.4067 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.5158 1.4199 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8741 -0.4035 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.0572 1.1758 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 10 1 0 0 0 0 2 10 1 0 0 0 0 4 19 1 0 0 0 0 5 6 1 0 0 0 0 5 12 1 0 0 0 0 6 18 1 0 0 0 0 7 8 1 0 0 0 0 7 18 1 0 0 0 0 8 19 1 0 0 0 0 9 11 1 0 0 0 0 9 25 1 0 0 0 0 10 13 1 0 0 0 0 11 12 1 0 0 0 0 11 14 2 0 0 0 0 12 21 1 1 0 0 0 13 15 1 0 0 0 0 13 19 1 1 0 0 0 14 17 1 0 0 0 0 14 18 1 0 0 0 0 15 16 1 0 0 0 0 15 22 1 1 0 0 0 16 20 1 0 0 0 0 16 23 2 0 0 0 0 17 20 1 1 0 0 0 17 25 1 0 0 0 0 18 3 1 6 0 0 0 19 20 1 6 0 0 0 20 24 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	350.21
Volume:	358.929
LogP:	1.892
LogD:	1.022
LogS:	-2.618
# Rotatable Bonds:	1
TPSA:	86.99
# H-Bond Aceptor:	5
# H-Bond Donor:	3
# Rings:	4
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.625
Synthetic Accessibility Score:	5.24
Fsp3:	0.85
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.828
MDCK Permeability:	3.081247632508166e-05
Pgp-inhibitor:	0.001
Pgp-substrate:	0.929
Human Intestinal Absorption (HIA):	0.021
20% Bioavailability (F20%):	0.788
30% Bioavailability (F30%):	0.013

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.749
Plasma Protein Binding (PPB):	77.30302429199219%
Volume Distribution (VD):	2.003
Pgp-substrate:	30.54552459716797%

ADMET: Metabolism

CYP1A2-inhibitor:	0.013
CYP1A2-substrate:	0.223
CYP2C19-inhibitor:	0.011
CYP2C19-substrate:	0.709
CYP2C9-inhibitor:	0.013
CYP2C9-substrate:	0.035
CYP2D6-inhibitor:	0.004
CYP2D6-substrate:	0.139
CYP3A4-inhibitor:	0.029
CYP3A4-substrate:	0.201

ADMET: Excretion

Clearance (CL):	4.072
Half-life (T1/2):	0.316

ADMET: Toxicity

hERG Blockers:	0.027
Human Hepatotoxicity (H-HT):	0.528
Drug-inuced Liver Injury (DILI):	0.887
AMES Toxicity:	0.417
Rat Oral Acute Toxicity:	0.942
Maximum Recommended Daily Dose:	0.966
Skin Sensitization:	0.395
Carcinogencity:	0.453
Eye Corrosion:	0.211
Eye Irritation:	0.037
Respiratory Toxicity:	0.982

Download Data

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

Natural Product: NPC204884

Natural Product ID:	NPC204884
*Common Name:**	GLVVTGQCCKZTDQ-CIQUPHSFSA-N
IUPAC Name:	n.a.
Synonyms:	Rel-Plicatilisin D
Standard InCHIKey:	GLVVTGQCCKZTDQ-CIQUPHSFSA-N
Standard InCHI:	InChI=1S/C20H30O5/c1-10(2)13-15(22)16(23)20(24)17-14-11(9-25-17)12(21)5-6-18(14,3)7-8-19(13,20)4/h10,12-13,15,17,21-22,24H,5-9H2,1-4H3/t12-,13-,15+,17-,18-,19+,20+/m0/s1
SMILES:	O[C@H]1CC[C@@]2(C3=C1CO[C@@H]3[C@]1(O)C(=O)[C@@H]([C@@H]([C@]1(CC2)C)C(C)C)O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2057718
PubChem CID:	62707594
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0001983] Dihydrofurans

*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
NPO32901	coprinus plicatilis	Species	Agaricaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22749279]

☑ 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	6

Activity Type	# Activity
Cell Line	6

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT65	Cell Line	HepG2	Homo sapiens	IC50	=	16900.0	nM	PMID[535965]
NPT165	Cell Line	HeLa	Homo sapiens	IC50	>	50000.0	nM	PMID[535965]
NPT82	Cell Line	MDA-MB-231	Homo sapiens	IC50	=	34800.0	nM	PMID[535965]
NPT547	Cell Line	BGC-823	Homo sapiens	IC50	=	35600.0	nM	PMID[535965]
NPT393	Cell Line	HCT-116	Homo sapiens	IC50	=	19800.0	nM	PMID[535965]
NPT1045	Cell Line	U2OS	Homo sapiens	IC50	=	39700.0	nM	PMID[535965]

☑ 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 NPC204884 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	266
0.1-0.2	1809
0.2-0.3	5814
0.3-0.4	11980
0.4-0.5	11757
0.5-0.6	7143
0.6-0.7	3536
0.7-0.8	381
0.8-0.85	10
0.85-0.9	0
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.8173	Intermediate Similarity	NPC177232
0.8173	Intermediate Similarity	NPC212465
0.8053	Intermediate Similarity	NPC54739
0.8	Intermediate Similarity	NPC101018
0.7885	Intermediate Similarity	NPC37408
0.7885	Intermediate Similarity	NPC469873
0.7863	Intermediate Similarity	NPC471999
0.7863	Intermediate Similarity	NPC472001
0.7863	Intermediate Similarity	NPC472000
0.7857	Intermediate Similarity	NPC472003
0.785	Intermediate Similarity	NPC477950
0.7798	Intermediate Similarity	NPC121099
0.7797	Intermediate Similarity	NPC107493
0.7788	Intermediate Similarity	NPC126691
0.7778	Intermediate Similarity	NPC472004
0.7768	Intermediate Similarity	NPC99760
0.7748	Intermediate Similarity	NPC117604
0.7736	Intermediate Similarity	NPC477949
0.7712	Intermediate Similarity	NPC46570
0.7699	Intermediate Similarity	NPC287311
0.7692	Intermediate Similarity	NPC477092
0.7679	Intermediate Similarity	NPC77089
0.7664	Intermediate Similarity	NPC109556
0.7658	Intermediate Similarity	NPC112780
0.7658	Intermediate Similarity	NPC144459
0.7652	Intermediate Similarity	NPC178289
0.7652	Intermediate Similarity	NPC326542
0.7636	Intermediate Similarity	NPC258532
0.7615	Intermediate Similarity	NPC105725
0.7615	Intermediate Similarity	NPC70369
0.7615	Intermediate Similarity	NPC295791
0.7611	Intermediate Similarity	NPC206595
0.7607	Intermediate Similarity	NPC475401
0.7589	Intermediate Similarity	NPC308191
0.757	Intermediate Similarity	NPC474313
0.7568	Intermediate Similarity	NPC179891
0.7545	Intermediate Similarity	NPC475871
0.7545	Intermediate Similarity	NPC159533
0.7545	Intermediate Similarity	NPC474775
0.7545	Intermediate Similarity	NPC475945
0.7524	Intermediate Similarity	NPC475788
0.7523	Intermediate Similarity	NPC475099
0.7523	Intermediate Similarity	NPC171759
0.7522	Intermediate Similarity	NPC273433
0.7522	Intermediate Similarity	NPC471400
0.7521	Intermediate Similarity	NPC144625
0.7521	Intermediate Similarity	NPC475305
0.75	Intermediate Similarity	NPC470541
0.75	Intermediate Similarity	NPC269642
0.748	Intermediate Similarity	NPC311534
0.748	Intermediate Similarity	NPC476078
0.748	Intermediate Similarity	NPC476091
0.7479	Intermediate Similarity	NPC79579
0.7479	Intermediate Similarity	NPC474585
0.7478	Intermediate Similarity	NPC207251
0.7477	Intermediate Similarity	NPC203659
0.7477	Intermediate Similarity	NPC149124
0.7477	Intermediate Similarity	NPC100487
0.7477	Intermediate Similarity	NPC220964
0.7477	Intermediate Similarity	NPC75531
0.7477	Intermediate Similarity	NPC475676
0.7477	Intermediate Similarity	NPC91771
0.7477	Intermediate Similarity	NPC142529
0.7477	Intermediate Similarity	NPC98165
0.746	Intermediate Similarity	NPC471234
0.7458	Intermediate Similarity	NPC153440
0.7456	Intermediate Similarity	NPC257240
0.7456	Intermediate Similarity	NPC5103
0.7455	Intermediate Similarity	NPC49393
0.7455	Intermediate Similarity	NPC474747
0.7453	Intermediate Similarity	NPC298919
0.7438	Intermediate Similarity	NPC129992
0.7436	Intermediate Similarity	NPC277583
0.7429	Intermediate Similarity	NPC144629
0.7419	Intermediate Similarity	NPC13071
0.7419	Intermediate Similarity	NPC472770
0.7419	Intermediate Similarity	NPC231529
0.7414	Intermediate Similarity	NPC312017
0.7414	Intermediate Similarity	NPC317210
0.7414	Intermediate Similarity	NPC194100
0.7414	Intermediate Similarity	NPC9848
0.7411	Intermediate Similarity	NPC54737
0.7411	Intermediate Similarity	NPC253223
0.7411	Intermediate Similarity	NPC243998
0.7407	Intermediate Similarity	NPC311904
0.7407	Intermediate Similarity	NPC471150
0.7407	Intermediate Similarity	NPC69385
0.7404	Intermediate Similarity	NPC97032
0.7398	Intermediate Similarity	NPC473265
0.7398	Intermediate Similarity	NPC473253
0.7398	Intermediate Similarity	NPC470882
0.7395	Intermediate Similarity	NPC19028
0.7395	Intermediate Similarity	NPC270850
0.7395	Intermediate Similarity	NPC9674
0.7395	Intermediate Similarity	NPC475041
0.7395	Intermediate Similarity	NPC305260
0.7395	Intermediate Similarity	NPC5292
0.7395	Intermediate Similarity	NPC230513
0.7387	Intermediate Similarity	NPC4620
0.7387	Intermediate Similarity	NPC110989
0.7387	Intermediate Similarity	NPC117185
0.7387	Intermediate Similarity	NPC26478
0.7387	Intermediate Similarity	NPC123505
0.7387	Intermediate Similarity	NPC472755
0.7383	Intermediate Similarity	NPC163228
0.7383	Intermediate Similarity	NPC261341
0.7381	Intermediate Similarity	NPC469673
0.7373	Intermediate Similarity	NPC475323
0.7368	Intermediate Similarity	NPC187876
0.7368	Intermediate Similarity	NPC470615
0.7368	Intermediate Similarity	NPC470257
0.7364	Intermediate Similarity	NPC472753
0.7364	Intermediate Similarity	NPC471401
0.7364	Intermediate Similarity	NPC474742
0.736	Intermediate Similarity	NPC220757
0.736	Intermediate Similarity	NPC196921
0.736	Intermediate Similarity	NPC475389
0.736	Intermediate Similarity	NPC473838
0.736	Intermediate Similarity	NPC241935
0.736	Intermediate Similarity	NPC279478
0.7355	Intermediate Similarity	NPC222688
0.7345	Intermediate Similarity	NPC473165
0.7345	Intermediate Similarity	NPC26617
0.7339	Intermediate Similarity	NPC222303
0.7339	Intermediate Similarity	NPC222011
0.7339	Intermediate Similarity	NPC470188
0.7333	Intermediate Similarity	NPC268530
0.7333	Intermediate Similarity	NPC142882
0.7333	Intermediate Similarity	NPC154491
0.7323	Intermediate Similarity	NPC476823
0.7321	Intermediate Similarity	NPC296950
0.7321	Intermediate Similarity	NPC146731
0.7321	Intermediate Similarity	NPC474741
0.7315	Intermediate Similarity	NPC476009
0.7311	Intermediate Similarity	NPC475372
0.7311	Intermediate Similarity	NPC475130
0.7311	Intermediate Similarity	NPC474286
0.7304	Intermediate Similarity	NPC41551
0.7304	Intermediate Similarity	NPC115257
0.7304	Intermediate Similarity	NPC475463
0.7304	Intermediate Similarity	NPC161816
0.7304	Intermediate Similarity	NPC477103
0.7304	Intermediate Similarity	NPC50223
0.7302	Intermediate Similarity	NPC34963
0.7302	Intermediate Similarity	NPC472769
0.7297	Intermediate Similarity	NPC471757
0.7297	Intermediate Similarity	NPC475986
0.7297	Intermediate Similarity	NPC78127
0.7297	Intermediate Similarity	NPC472754
0.7297	Intermediate Similarity	NPC225353
0.7297	Intermediate Similarity	NPC474709
0.7297	Intermediate Similarity	NPC470840
0.7297	Intermediate Similarity	NPC185530
0.7295	Intermediate Similarity	NPC473979
0.7295	Intermediate Similarity	NPC472399
0.7295	Intermediate Similarity	NPC469789
0.7295	Intermediate Similarity	NPC471392
0.729	Intermediate Similarity	NPC473331
0.7288	Intermediate Similarity	NPC138372
0.7288	Intermediate Similarity	NPC190286
0.7288	Intermediate Similarity	NPC106228
0.7281	Intermediate Similarity	NPC10150
0.7281	Intermediate Similarity	NPC65941
0.7281	Intermediate Similarity	NPC233379
0.7281	Intermediate Similarity	NPC14862
0.7281	Intermediate Similarity	NPC474664
0.7281	Intermediate Similarity	NPC329417
0.728	Intermediate Similarity	NPC470880
0.728	Intermediate Similarity	NPC35109
0.7273	Intermediate Similarity	NPC186861
0.7273	Intermediate Similarity	NPC4021
0.7273	Intermediate Similarity	NPC474718
0.7273	Intermediate Similarity	NPC159456
0.7273	Intermediate Similarity	NPC471381
0.7265	Intermediate Similarity	NPC469496
0.7265	Intermediate Similarity	NPC469454
0.7265	Intermediate Similarity	NPC108721
0.7265	Intermediate Similarity	NPC46269
0.7265	Intermediate Similarity	NPC73300
0.7265	Intermediate Similarity	NPC106395
0.7265	Intermediate Similarity	NPC469463
0.7258	Intermediate Similarity	NPC287423
0.7257	Intermediate Similarity	NPC474101
0.7257	Intermediate Similarity	NPC223450
0.7257	Intermediate Similarity	NPC44004
0.7257	Intermediate Similarity	NPC291643
0.7257	Intermediate Similarity	NPC190867
0.7257	Intermediate Similarity	NPC166607
0.725	Intermediate Similarity	NPC312536
0.725	Intermediate Similarity	NPC42673
0.7248	Intermediate Similarity	NPC213947
0.7248	Intermediate Similarity	NPC254121
0.7248	Intermediate Similarity	NPC161493
0.7248	Intermediate Similarity	NPC170143
0.7248	Intermediate Similarity	NPC108475
0.7244	Intermediate Similarity	NPC469674
0.7244	Intermediate Similarity	NPC58029
0.7244	Intermediate Similarity	NPC224623
0.7241	Intermediate Similarity	NPC317107
0.7241	Intermediate Similarity	NPC475668

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 NPC204884 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	283
0.1-0.2	2543
0.2-0.3	3745
0.3-0.4	1757
0.4-0.5	466
0.5-0.6	253
0.6-0.7	99
0.7-0.8	4
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
0.7456	Intermediate Similarity	NPD6371	Approved
0.7345	Intermediate Similarity	NPD7899	Clinical (unspecified phase)
0.719	Intermediate Similarity	NPD6059	Approved
0.719	Intermediate Similarity	NPD6054	Approved
0.719	Intermediate Similarity	NPD6319	Approved
0.7179	Intermediate Similarity	NPD6053	Discontinued
0.7155	Intermediate Similarity	NPD4634	Approved
0.7131	Intermediate Similarity	NPD6016	Approved
0.7131	Intermediate Similarity	NPD6015	Approved
0.7073	Intermediate Similarity	NPD5988	Approved
0.7073	Intermediate Similarity	NPD6370	Approved
0.7008	Intermediate Similarity	NPD7319	Approved
0.6991	Remote Similarity	NPD5211	Phase 2
0.6975	Remote Similarity	NPD4632	Approved
0.696	Remote Similarity	NPD7492	Approved
0.6937	Remote Similarity	NPD4755	Approved
0.6905	Remote Similarity	NPD7507	Approved
0.6905	Remote Similarity	NPD6616	Approved
0.687	Remote Similarity	NPD5141	Approved
0.685	Remote Similarity	NPD8293	Discontinued
0.685	Remote Similarity	NPD7078	Approved
0.6838	Remote Similarity	NPD7320	Approved
0.6818	Remote Similarity	NPD5282	Discontinued
0.6814	Remote Similarity	NPD4700	Approved
0.6814	Remote Similarity	NPD5285	Approved
0.6814	Remote Similarity	NPD4696	Approved
0.6814	Remote Similarity	NPD5286	Approved
0.681	Remote Similarity	NPD7128	Approved
0.681	Remote Similarity	NPD6402	Approved
0.681	Remote Similarity	NPD6675	Approved
0.681	Remote Similarity	NPD5739	Approved
0.6803	Remote Similarity	NPD7115	Discovery
0.6797	Remote Similarity	NPD7736	Approved
0.678	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6757	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6752	Remote Similarity	NPD5697	Approved
0.6752	Remote Similarity	NPD5701	Approved
0.675	Remote Similarity	NPD8297	Approved
0.6696	Remote Similarity	NPD5225	Approved
0.6696	Remote Similarity	NPD5226	Approved
0.6696	Remote Similarity	NPD4633	Approved
0.6696	Remote Similarity	NPD5224	Approved
0.6695	Remote Similarity	NPD6899	Approved
0.6695	Remote Similarity	NPD6881	Approved
0.6695	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6009	Approved
0.6667	Remote Similarity	NPD6033	Approved
0.6639	Remote Similarity	NPD6012	Approved
0.6639	Remote Similarity	NPD6372	Approved
0.6639	Remote Similarity	NPD6013	Approved
0.6639	Remote Similarity	NPD6373	Approved
0.6639	Remote Similarity	NPD6014	Approved
0.6638	Remote Similarity	NPD5174	Approved
0.6638	Remote Similarity	NPD5175	Approved
0.6636	Remote Similarity	NPD7983	Approved
0.661	Remote Similarity	NPD6412	Phase 2
0.6609	Remote Similarity	NPD5223	Approved
0.6606	Remote Similarity	NPD4753	Phase 2
0.6587	Remote Similarity	NPD5983	Phase 2
0.6583	Remote Similarity	NPD6883	Approved
0.6583	Remote Similarity	NPD7102	Approved
0.6583	Remote Similarity	NPD7290	Approved
0.6577	Remote Similarity	NPD5778	Approved
0.6577	Remote Similarity	NPD5779	Approved
0.6555	Remote Similarity	NPD6011	Approved
0.6545	Remote Similarity	NPD5785	Approved
0.6529	Remote Similarity	NPD6869	Approved
0.6529	Remote Similarity	NPD6649	Approved
0.6529	Remote Similarity	NPD6617	Approved
0.6529	Remote Similarity	NPD8130	Phase 1
0.6529	Remote Similarity	NPD6650	Approved
0.6529	Remote Similarity	NPD6847	Approved
0.6525	Remote Similarity	NPD4767	Approved
0.6525	Remote Similarity	NPD6008	Approved
0.6525	Remote Similarity	NPD4768	Approved
0.6496	Remote Similarity	NPD4754	Approved
0.6491	Remote Similarity	NPD6084	Phase 2
0.6491	Remote Similarity	NPD6083	Phase 2
0.6484	Remote Similarity	NPD7604	Phase 2
0.6481	Remote Similarity	NPD5786	Approved
0.6481	Remote Similarity	NPD4249	Approved
0.6475	Remote Similarity	NPD6882	Approved
0.6466	Remote Similarity	NPD1700	Approved
0.646	Remote Similarity	NPD5695	Phase 3
0.6457	Remote Similarity	NPD8033	Approved
0.6446	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6435	Remote Similarity	NPD4225	Approved
0.6422	Remote Similarity	NPD7524	Approved
0.6422	Remote Similarity	NPD4250	Approved
0.6422	Remote Similarity	NPD4251	Approved
0.6417	Remote Similarity	NPD4729	Approved
0.6417	Remote Similarity	NPD6686	Approved
0.6417	Remote Similarity	NPD5128	Approved
0.6417	Remote Similarity	NPD4730	Approved
0.6415	Remote Similarity	NPD6435	Approved
0.64	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6396	Remote Similarity	NPD46	Approved
0.6396	Remote Similarity	NPD6698	Approved
0.6393	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6385	Remote Similarity	NPD6336	Discontinued
0.6379	Remote Similarity	NPD7639	Approved
0.6379	Remote Similarity	NPD7640	Approved
0.6355	Remote Similarity	NPD5362	Discontinued
0.6349	Remote Similarity	NPD7327	Approved
0.6349	Remote Similarity	NPD7328	Approved
0.6339	Remote Similarity	NPD7637	Suspended
0.6328	Remote Similarity	NPD8516	Approved
0.6328	Remote Similarity	NPD8517	Approved
0.6328	Remote Similarity	NPD8515	Approved
0.6328	Remote Similarity	NPD8513	Phase 3
0.632	Remote Similarity	NPD6274	Approved
0.6316	Remote Similarity	NPD5210	Approved
0.6316	Remote Similarity	NPD4629	Approved
0.6316	Remote Similarity	NPD5956	Approved
0.6311	Remote Similarity	NPD5251	Approved
0.6311	Remote Similarity	NPD5248	Approved
0.6311	Remote Similarity	NPD5250	Approved
0.6311	Remote Similarity	NPD5247	Approved
0.6311	Remote Similarity	NPD5249	Phase 3
0.6306	Remote Similarity	NPD1695	Approved
0.6303	Remote Similarity	NPD4056	Clinical (unspecified phase)
0.6303	Remote Similarity	NPD4057	Clinical (unspecified phase)
0.6299	Remote Similarity	NPD4522	Approved
0.6299	Remote Similarity	NPD7516	Approved
0.6296	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6293	Remote Similarity	NPD7638	Approved
0.6293	Remote Similarity	NPD5696	Approved
0.6283	Remote Similarity	NPD4202	Approved
0.6271	Remote Similarity	NPD7632	Discontinued
0.6262	Remote Similarity	NPD4269	Approved
0.6262	Remote Similarity	NPD4800	Clinical (unspecified phase)
0.6262	Remote Similarity	NPD4270	Approved
0.6261	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6261	Remote Similarity	NPD5222	Approved
0.6261	Remote Similarity	NPD4697	Phase 3
0.6261	Remote Similarity	NPD5221	Approved
0.626	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.626	Remote Similarity	NPD5216	Approved
0.626	Remote Similarity	NPD5217	Approved
0.626	Remote Similarity	NPD5215	Approved
0.625	Remote Similarity	NPD8294	Approved
0.625	Remote Similarity	NPD8377	Approved
0.6226	Remote Similarity	NPD4822	Approved
0.6226	Remote Similarity	NPD4820	Approved
0.6226	Remote Similarity	NPD4819	Approved
0.6226	Remote Similarity	NPD5368	Approved
0.6226	Remote Similarity	NPD4821	Approved
0.6226	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6222	Remote Similarity	NPD6845	Suspended
0.6207	Remote Similarity	NPD5173	Approved
0.6204	Remote Similarity	NPD6695	Phase 3
0.6202	Remote Similarity	NPD8378	Approved
0.6202	Remote Similarity	NPD8380	Approved
0.6202	Remote Similarity	NPD8296	Approved
0.6202	Remote Similarity	NPD8335	Approved
0.6202	Remote Similarity	NPD8379	Approved
0.6198	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6195	Remote Similarity	NPD5693	Phase 1
0.6195	Remote Similarity	NPD6411	Approved
0.6182	Remote Similarity	NPD5279	Phase 3
0.6179	Remote Similarity	NPD5169	Approved
0.6179	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.6179	Remote Similarity	NPD5135	Approved
0.6172	Remote Similarity	NPD7100	Approved
0.6172	Remote Similarity	NPD7101	Approved
0.6168	Remote Similarity	NPD5369	Approved
0.6161	Remote Similarity	NPD5328	Approved
0.6148	Remote Similarity	NPD7260	Phase 2
0.6147	Remote Similarity	NPD4786	Approved
0.6147	Remote Similarity	NPD3665	Phase 1
0.6147	Remote Similarity	NPD3666	Approved
0.6147	Remote Similarity	NPD3133	Approved
0.6147	Remote Similarity	NPD4197	Approved
0.6142	Remote Similarity	NPD6317	Approved
0.614	Remote Similarity	NPD6399	Phase 3
0.6129	Remote Similarity	NPD5127	Approved
0.6111	Remote Similarity	NPD3667	Approved
0.6107	Remote Similarity	NPD8328	Phase 3
0.6094	Remote Similarity	NPD6313	Approved
0.6094	Remote Similarity	NPD6335	Approved
0.6094	Remote Similarity	NPD6314	Approved
0.6091	Remote Similarity	NPD5329	Approved
0.6091	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6091	Remote Similarity	NPD5363	Approved
0.609	Remote Similarity	NPD8074	Phase 3
0.6077	Remote Similarity	NPD6908	Approved
0.6077	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.6077	Remote Similarity	NPD7503	Approved
0.6077	Remote Similarity	NPD6921	Approved
0.6077	Remote Similarity	NPD6909	Approved
0.6075	Remote Similarity	NPD4252	Approved
0.6055	Remote Similarity	NPD7154	Phase 3
0.6055	Remote Similarity	NPD6110	Phase 1
0.6053	Remote Similarity	NPD6079	Approved
0.605	Remote Similarity	NPD4159	Approved
0.605	Remote Similarity	NPD5344	Discontinued
0.6038	Remote Similarity	NPD4268	Approved
0.6038	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6038	Remote Similarity	NPD4271	Approved
0.6036	Remote Similarity	NPD5280	Approved

Bioactivity similarity: Similar Natural Products in NPASS

Bioactivity similarity was calculated based on bioactivity descriptors of compounds. The bioactivity descriptors were calculated by a recently developed AI algorithm Chemical Checker (CC) [Nature Biotechnology, 38:1087–1096, 2020; Nature Communications, 12:3932, 2021], which evaluated bioactivity similarities at five levels:
☉ A: chemistry similarity;
☉ B: biological targets similarity;
☉ C: networks similarity;
☉ D: cell-based bioactivity similarity;
☉ E: similarity based on clinical data.

Those 5 categories of CC bioactivity descriptors were calculated and then subjected to manifold projection using UMAP algorithm, to project all NPs on a 2-Dimensional space. The current NP was highlighted with a small circle in the 2-D map. Below figures: left-to-right, A-to-E.

A: chemistry similarity

B: biological targets similarity

C: networks similarity

D: cell-based bioactivity similarity

E: similarity based on clinical data