NPASS Compound

Structure

NPC169766 OpenBabel07101718322D 23 24 0 0 0 0 0 0 0 0999 V2000 7.1449 1.7024 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.0109 3.2024 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1977 3.8745 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7330 2.2272 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9487 2.7024 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8147 1.2024 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8147 3.2024 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6808 1.7024 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.2788 3.2024 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.4128 2.7024 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0388 2.5873 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.1449 2.7024 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9898 2.8963 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9487 1.7024 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6808 2.7024 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1691 1.6092 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0827 1.2024 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5000 0.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9781 0.2079 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -1.4945 0.9706 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7213 -0.4612 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.5468 3.2024 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 12 1 0 0 0 0 2 12 1 0 0 0 0 3 13 1 0 0 0 0 4 13 1 0 0 0 0 5 7 1 0 0 0 0 5 14 2 0 0 0 0 6 8 2 0 0 0 0 6 14 1 0 0 0 0 7 15 2 0 0 0 0 8 15 1 0 0 0 0 9 10 1 0 0 0 0 9 12 2 0 0 0 0 10 23 1 0 0 0 0 11 13 1 0 0 0 0 11 16 1 0 0 0 0 14 17 1 0 0 0 0 15 23 1 0 0 0 0 16 17 2 0 0 0 0 16 18 1 0 0 0 0 17 19 1 0 0 0 0 18 20 2 0 0 0 0 18 21 1 0 0 0 0 19 20 1 0 0 0 0 19 22 2 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	313.17
Volume:	338.979
LogP:	5.259
LogD:	4.318
LogS:	-3.135
# Rotatable Bonds:	5
TPSA:	65.48
# H-Bond Aceptor:	4
# H-Bond Donor:	3
# Rings:	2
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.691
Synthetic Accessibility Score:	2.894
Fsp3:	0.263
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:	-4.8
MDCK Permeability:	1.5887952031334862e-05
Pgp-inhibitor:	0.507
Pgp-substrate:	0.274
Human Intestinal Absorption (HIA):	0.006
20% Bioavailability (F20%):	0.585
30% Bioavailability (F30%):	0.008

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.083
Plasma Protein Binding (PPB):	97.9638671875%
Volume Distribution (VD):	2.847
Pgp-substrate:	1.982932686805725%

ADMET: Metabolism

CYP1A2-inhibitor:	0.934
CYP1A2-substrate:	0.783
CYP2C19-inhibitor:	0.847
CYP2C19-substrate:	0.072
CYP2C9-inhibitor:	0.821
CYP2C9-substrate:	0.959
CYP2D6-inhibitor:	0.906
CYP2D6-substrate:	0.9
CYP3A4-inhibitor:	0.329
CYP3A4-substrate:	0.202

ADMET: Excretion

Clearance (CL):	11.289
Half-life (T1/2):	0.442

ADMET: Toxicity

hERG Blockers:	0.038
Human Hepatotoxicity (H-HT):	0.97
Drug-inuced Liver Injury (DILI):	0.986
AMES Toxicity:	0.016
Rat Oral Acute Toxicity:	0.045
Maximum Recommended Daily Dose:	0.062
Skin Sensitization:	0.318
Carcinogencity:	0.237
Eye Corrosion:	0.003
Eye Irritation:	0.081
Respiratory Toxicity:	0.426

Download Data

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

Natural Product: NPC169766

Natural Product ID:	NPC169766
*Common Name:**
IUPAC Name:	3-[4-(3-methylbut-2-enoxy)phenyl]-4-(2-methylpropyl)pyrrole-2,5-dione
Synonyms:
Standard InCHIKey:	AILGRWSIRAPLCJ-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C19H23NO3/c1-12(2)9-10-23-15-7-5-14(6-8-15)17-16(11-13(3)4)18(21)20-19(17)22/h5-9,13H,10-11H2,1-4H3,(H,20,21,22)
SMILES:	CC(=CCOc1ccc(cc1)C1=C(CC(C)C)C(=NC1=O)O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL471118
PubChem CID:	5255246
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0002341] Phenol ethers

*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
NPO30573	Antrodia camphorata	Species	Fomitopsidaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[14738384]
NPO30573	Antrodia camphorata	Species	Fomitopsidaceae	Eukaryota	fruiting bodies	n.a.	n.a.	PMID[16643055]
NPO30573	Antrodia camphorata	Species	Fomitopsidaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17559265]
NPO32621	antrodia cinnamomea	Species	Fomitopsidaceae	Eukaryota	mycelia	n.a.	n.a.	PMID[18522430]
NPO30573	Antrodia camphorata	Species	Fomitopsidaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24387703]
NPO32621	antrodia cinnamomea	Species	Fomitopsidaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[28898082]
NPO30573	Antrodia camphorata	Species	Fomitopsidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]

☑ 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
ED50	1
IC50	2
Others	2

Activity Type	# Activity
Cell Line	2
Individual Protein	2
NON-MOLECULAR	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT113	Cell Line	RAW264.7	Mus musculus	Activity	=	10.6	uM	PMID[454270]
NPT113	Cell Line	RAW264.7	Mus musculus	Activity	=	69.1	%	PMID[454270]
NPT4524	Individual Protein	Genome polyprotein	Hepatitis C virus genotype 1a (isolate H) (HCV)	IC50	=	54000.0	nM	PMID[454271]
NPT4524	Individual Protein	Genome polyprotein	Hepatitis C virus genotype 1a (isolate H) (HCV)	IC50	=	54000	nM	PMID[23398362]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	ED50	=	3.6	ug ml-1	PMID[454269]

☑ 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 NPC169766 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	177
0.1-0.2	1287
0.2-0.3	4666
0.3-0.4	12135
0.4-0.5	5236
0.5-0.6	12560
0.6-0.7	6392
0.7-0.8	237
0.8-0.85	5
0.85-0.9	1
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.8797	High Similarity	NPC132308
0.8529	High Similarity	NPC196708
0.8175	Intermediate Similarity	NPC470392
0.8092	Intermediate Similarity	NPC263835
0.8077	Intermediate Similarity	NPC293424
0.8074	Intermediate Similarity	NPC474476
0.7974	Intermediate Similarity	NPC71205
0.7943	Intermediate Similarity	NPC106606
0.7914	Intermediate Similarity	NPC328070
0.7879	Intermediate Similarity	NPC43275
0.7842	Intermediate Similarity	NPC477645
0.7836	Intermediate Similarity	NPC268348
0.7812	Intermediate Similarity	NPC166837
0.7762	Intermediate Similarity	NPC471316
0.7762	Intermediate Similarity	NPC471201
0.7692	Intermediate Similarity	NPC473055
0.7692	Intermediate Similarity	NPC473052
0.7681	Intermediate Similarity	NPC218323
0.7664	Intermediate Similarity	NPC221798
0.7652	Intermediate Similarity	NPC19290
0.7639	Intermediate Similarity	NPC322526
0.7612	Intermediate Similarity	NPC256369
0.7609	Intermediate Similarity	NPC29477
0.7606	Intermediate Similarity	NPC266425
0.7564	Intermediate Similarity	NPC293164
0.7564	Intermediate Similarity	NPC471394
0.7536	Intermediate Similarity	NPC95733
0.7536	Intermediate Similarity	NPC62101
0.7519	Intermediate Similarity	NPC234639
0.7518	Intermediate Similarity	NPC69403
0.7518	Intermediate Similarity	NPC291189
0.75	Intermediate Similarity	NPC252004
0.75	Intermediate Similarity	NPC67080
0.7483	Intermediate Similarity	NPC153644
0.7481	Intermediate Similarity	NPC17693
0.7481	Intermediate Similarity	NPC264976
0.748	Intermediate Similarity	NPC470393
0.7467	Intermediate Similarity	NPC132771
0.7464	Intermediate Similarity	NPC211218
0.746	Intermediate Similarity	NPC192596
0.7448	Intermediate Similarity	NPC307682
0.7444	Intermediate Similarity	NPC51345
0.7431	Intermediate Similarity	NPC473360
0.7429	Intermediate Similarity	NPC475236
0.7426	Intermediate Similarity	NPC53596
0.7426	Intermediate Similarity	NPC289330
0.7426	Intermediate Similarity	NPC474874
0.7426	Intermediate Similarity	NPC17388
0.7426	Intermediate Similarity	NPC160120
0.7426	Intermediate Similarity	NPC471308
0.7424	Intermediate Similarity	NPC109241
0.7413	Intermediate Similarity	NPC471953
0.7402	Intermediate Similarity	NPC108875
0.7402	Intermediate Similarity	NPC38209
0.7402	Intermediate Similarity	NPC38079
0.74	Intermediate Similarity	NPC313414
0.74	Intermediate Similarity	NPC9373
0.7394	Intermediate Similarity	NPC120251
0.7394	Intermediate Similarity	NPC939
0.7388	Intermediate Similarity	NPC258992
0.7388	Intermediate Similarity	NPC128249
0.7386	Intermediate Similarity	NPC478189
0.7381	Intermediate Similarity	NPC51633
0.7376	Intermediate Similarity	NPC296712
0.7372	Intermediate Similarity	NPC473051
0.7372	Intermediate Similarity	NPC473050
0.7364	Intermediate Similarity	NPC151530
0.7364	Intermediate Similarity	NPC157473
0.7357	Intermediate Similarity	NPC470858
0.7355	Intermediate Similarity	NPC56635
0.7338	Intermediate Similarity	NPC118853
0.7338	Intermediate Similarity	NPC473942
0.7328	Intermediate Similarity	NPC183648
0.7324	Intermediate Similarity	NPC2596
0.7324	Intermediate Similarity	NPC283079
0.7323	Intermediate Similarity	NPC298224
0.7319	Intermediate Similarity	NPC474862
0.7313	Intermediate Similarity	NPC296526
0.7313	Intermediate Similarity	NPC303370
0.7303	Intermediate Similarity	NPC324081
0.7287	Intermediate Similarity	NPC1065
0.7287	Intermediate Similarity	NPC176971
0.7287	Intermediate Similarity	NPC231705
0.7287	Intermediate Similarity	NPC326447
0.7286	Intermediate Similarity	NPC89630
0.7273	Intermediate Similarity	NPC57879
0.7273	Intermediate Similarity	NPC23332
0.7266	Intermediate Similarity	NPC471314
0.7266	Intermediate Similarity	NPC471315
0.7261	Intermediate Similarity	NPC471203
0.7259	Intermediate Similarity	NPC470860
0.7254	Intermediate Similarity	NPC153990
0.7254	Intermediate Similarity	NPC251571
0.7252	Intermediate Similarity	NPC259554
0.7239	Intermediate Similarity	NPC114144
0.7237	Intermediate Similarity	NPC290404
0.7231	Intermediate Similarity	NPC142297
0.723	Intermediate Similarity	NPC187826
0.723	Intermediate Similarity	NPC160747
0.7226	Intermediate Similarity	NPC61779
0.7222	Intermediate Similarity	NPC45191
0.7222	Intermediate Similarity	NPC255550
0.7222	Intermediate Similarity	NPC308885
0.7214	Intermediate Similarity	NPC4181
0.7214	Intermediate Similarity	NPC257976
0.7214	Intermediate Similarity	NPC11799
0.7214	Intermediate Similarity	NPC164778
0.7214	Intermediate Similarity	NPC242372
0.7214	Intermediate Similarity	NPC141252
0.7211	Intermediate Similarity	NPC204592
0.7211	Intermediate Similarity	NPC236974
0.7211	Intermediate Similarity	NPC144027
0.7209	Intermediate Similarity	NPC128730
0.7209	Intermediate Similarity	NPC473855
0.7206	Intermediate Similarity	NPC469954
0.7203	Intermediate Similarity	NPC478147
0.7203	Intermediate Similarity	NPC155838
0.7197	Intermediate Similarity	NPC474149
0.7192	Intermediate Similarity	NPC203817
0.7192	Intermediate Similarity	NPC218530
0.7183	Intermediate Similarity	NPC301713
0.7181	Intermediate Similarity	NPC212850
0.7181	Intermediate Similarity	NPC83289
0.7181	Intermediate Similarity	NPC189724
0.7176	Intermediate Similarity	NPC31274
0.7174	Intermediate Similarity	NPC193193
0.7174	Intermediate Similarity	NPC31314
0.7174	Intermediate Similarity	NPC321133
0.7172	Intermediate Similarity	NPC93882
0.7172	Intermediate Similarity	NPC274732
0.7172	Intermediate Similarity	NPC130595
0.7172	Intermediate Similarity	NPC470977
0.7172	Intermediate Similarity	NPC196979
0.7172	Intermediate Similarity	NPC470976
0.7164	Intermediate Similarity	NPC26524
0.7163	Intermediate Similarity	NPC312404
0.7163	Intermediate Similarity	NPC273686
0.7153	Intermediate Similarity	NPC21831
0.7153	Intermediate Similarity	NPC311091
0.7153	Intermediate Similarity	NPC35961
0.7153	Intermediate Similarity	NPC187547
0.7153	Intermediate Similarity	NPC238309
0.7153	Intermediate Similarity	NPC52029
0.7153	Intermediate Similarity	NPC471033
0.7153	Intermediate Similarity	NPC195749
0.7152	Intermediate Similarity	NPC476194
0.7143	Intermediate Similarity	NPC114298
0.7143	Intermediate Similarity	NPC161544
0.7134	Intermediate Similarity	NPC207675
0.7134	Intermediate Similarity	NPC212699
0.7132	Intermediate Similarity	NPC33717
0.7132	Intermediate Similarity	NPC2518
0.7123	Intermediate Similarity	NPC313737
0.7123	Intermediate Similarity	NPC6854
0.7123	Intermediate Similarity	NPC105541
0.7123	Intermediate Similarity	NPC285078
0.7122	Intermediate Similarity	NPC158949
0.7122	Intermediate Similarity	NPC83279
0.7121	Intermediate Similarity	NPC258056
0.7115	Intermediate Similarity	NPC256689
0.7115	Intermediate Similarity	NPC123011
0.7114	Intermediate Similarity	NPC240593
0.7114	Intermediate Similarity	NPC470397
0.7114	Intermediate Similarity	NPC156910
0.7114	Intermediate Similarity	NPC470398
0.7113	Intermediate Similarity	NPC88403
0.7113	Intermediate Similarity	NPC473626
0.7113	Intermediate Similarity	NPC280767
0.7111	Intermediate Similarity	NPC235250
0.7103	Intermediate Similarity	NPC327457
0.7103	Intermediate Similarity	NPC282230
0.7103	Intermediate Similarity	NPC298268
0.7103	Intermediate Similarity	NPC245395
0.7103	Intermediate Similarity	NPC469929
0.7103	Intermediate Similarity	NPC114102
0.7103	Intermediate Similarity	NPC86774
0.7103	Intermediate Similarity	NPC183348
0.7101	Intermediate Similarity	NPC319950
0.7101	Intermediate Similarity	NPC315542
0.7091	Intermediate Similarity	NPC211713
0.7091	Intermediate Similarity	NPC88378
0.7089	Intermediate Similarity	NPC319320
0.7089	Intermediate Similarity	NPC287757
0.7087	Intermediate Similarity	NPC100870
0.7087	Intermediate Similarity	NPC471576
0.7086	Intermediate Similarity	NPC908
0.7086	Intermediate Similarity	NPC138438
0.7083	Intermediate Similarity	NPC226661
0.7081	Intermediate Similarity	NPC254700
0.708	Intermediate Similarity	NPC240664
0.7077	Intermediate Similarity	NPC8302
0.7071	Intermediate Similarity	NPC142577
0.7071	Intermediate Similarity	NPC201777
0.7068	Intermediate Similarity	NPC46844
0.7067	Intermediate Similarity	NPC148738
0.7067	Intermediate Similarity	NPC327612
0.7067	Intermediate Similarity	NPC319870
0.7067	Intermediate Similarity	NPC73078
0.7067	Intermediate Similarity	NPC188879
0.7063	Intermediate Similarity	NPC476353

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 NPC169766 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	143
0.1-0.2	687
0.2-0.3	968
0.3-0.4	1949
0.4-0.5	2560
0.5-0.6	2064
0.6-0.7	726
0.7-0.8	53
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
0.7905	Intermediate Similarity	NPD7131	Phase 3
0.7752	Intermediate Similarity	NPD821	Approved
0.7724	Intermediate Similarity	NPD7596	Clinical (unspecified phase)
0.7692	Intermediate Similarity	NPD1241	Discontinued
0.766	Intermediate Similarity	NPD3058	Clinical (unspecified phase)
0.7632	Intermediate Similarity	NPD6502	Phase 2
0.7606	Intermediate Similarity	NPD3140	Approved
0.7606	Intermediate Similarity	NPD3142	Approved
0.7586	Intermediate Similarity	NPD2161	Phase 2
0.7584	Intermediate Similarity	NPD4357	Discontinued
0.7483	Intermediate Similarity	NPD6390	Discontinued
0.7483	Intermediate Similarity	NPD3655	Clinical (unspecified phase)
0.7464	Intermediate Similarity	NPD3676	Clinical (unspecified phase)
0.7447	Intermediate Similarity	NPD2614	Approved
0.7436	Intermediate Similarity	NPD7318	Phase 3
0.7432	Intermediate Similarity	NPD2976	Clinical (unspecified phase)
0.7379	Intermediate Similarity	NPD2157	Approved
0.7376	Intermediate Similarity	NPD1712	Approved
0.7368	Intermediate Similarity	NPD4186	Clinical (unspecified phase)
0.7342	Intermediate Similarity	NPD6971	Discontinued
0.7338	Intermediate Similarity	NPD3685	Discontinued
0.7324	Intermediate Similarity	NPD682	Discontinued
0.7308	Intermediate Similarity	NPD7317	Phase 3
0.7292	Intermediate Similarity	NPD7477	Discontinued
0.729	Intermediate Similarity	NPD2592	Discontinued
0.7287	Intermediate Similarity	NPD3134	Approved
0.7279	Intermediate Similarity	NPD1894	Discontinued
0.7279	Intermediate Similarity	NPD3846	Clinical (unspecified phase)
0.7261	Intermediate Similarity	NPD7972	Discontinued
0.7244	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7234	Intermediate Similarity	NPD2797	Approved
0.723	Intermediate Similarity	NPD5712	Approved
0.723	Intermediate Similarity	NPD4476	Approved
0.723	Intermediate Similarity	NPD4477	Approved
0.7222	Intermediate Similarity	NPD3144	Approved
0.7222	Intermediate Similarity	NPD3145	Approved
0.7214	Intermediate Similarity	NPD4129	Approved
0.7212	Intermediate Similarity	NPD5557	Phase 1
0.7211	Intermediate Similarity	NPD743	Approved
0.7211	Intermediate Similarity	NPD696	Discontinued
0.7208	Intermediate Similarity	NPD3873	Phase 3
0.7208	Intermediate Similarity	NPD3869	Phase 3
0.7197	Intermediate Similarity	NPD3812	Clinical (unspecified phase)
0.7197	Intermediate Similarity	NPD7577	Discontinued
0.7192	Intermediate Similarity	NPD654	Phase 3
0.7178	Intermediate Similarity	NPD3451	Clinical (unspecified phase)
0.7176	Intermediate Similarity	NPD2684	Approved
0.7174	Intermediate Similarity	NPD2667	Approved
0.7174	Intermediate Similarity	NPD2668	Approved
0.7172	Intermediate Similarity	NPD2674	Phase 3
0.7169	Intermediate Similarity	NPD3823	Discontinued
0.7163	Intermediate Similarity	NPD196	Phase 1
0.7153	Intermediate Similarity	NPD5163	Phase 2
0.7152	Intermediate Similarity	NPD6331	Phase 2
0.7134	Intermediate Similarity	NPD2541	Clinical (unspecified phase)
0.7133	Intermediate Similarity	NPD7153	Discontinued
0.7133	Intermediate Similarity	NPD4993	Discontinued
0.7122	Intermediate Similarity	NPD3847	Discontinued
0.7115	Intermediate Similarity	NPD3866	Clinical (unspecified phase)
0.7114	Intermediate Similarity	NPD1725	Approved
0.7113	Intermediate Similarity	NPD3567	Approved
0.7113	Intermediate Similarity	NPD3568	Approved
0.7107	Intermediate Similarity	NPD5967	Approved
0.7103	Intermediate Similarity	NPD1048	Approved
0.7097	Intermediate Similarity	NPD1670	Discontinued
0.7097	Intermediate Similarity	NPD7427	Discontinued
0.7092	Intermediate Similarity	NPD6583	Phase 3
0.7092	Intermediate Similarity	NPD6582	Phase 2
0.7091	Intermediate Similarity	NPD3909	Discontinued
0.708	Intermediate Similarity	NPD1758	Phase 1
0.7075	Intermediate Similarity	NPD6355	Discontinued
0.7063	Intermediate Similarity	NPD5647	Approved
0.7055	Intermediate Similarity	NPD5745	Approved
0.7055	Intermediate Similarity	NPD7608	Discontinued
0.7039	Intermediate Similarity	NPD5481	Discontinued
0.7039	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.7039	Intermediate Similarity	NPD4110	Phase 3
0.7034	Intermediate Similarity	NPD3136	Phase 2
0.7032	Intermediate Similarity	NPD1975	Clinical (unspecified phase)
0.7029	Intermediate Similarity	NPD1759	Phase 1
0.7029	Intermediate Similarity	NPD9545	Approved
0.7024	Intermediate Similarity	NPD5192	Clinical (unspecified phase)
0.7021	Intermediate Similarity	NPD1481	Phase 2
0.7021	Intermediate Similarity	NPD9717	Approved
0.7021	Intermediate Similarity	NPD2231	Phase 2
0.7021	Intermediate Similarity	NPD2235	Phase 2
0.702	Intermediate Similarity	NPD4149	Clinical (unspecified phase)
0.7011	Intermediate Similarity	NPD4466	Phase 1
0.7006	Intermediate Similarity	NPD824	Approved
0.7006	Intermediate Similarity	NPD5811	Approved
0.7	Intermediate Similarity	NPD2239	Approved
0.7	Intermediate Similarity	NPD2379	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD2240	Approved
0.6988	Remote Similarity	NPD2822	Clinical (unspecified phase)
0.6987	Remote Similarity	NPD5586	Clinical (unspecified phase)
0.6986	Remote Similarity	NPD6798	Discontinued
0.6986	Remote Similarity	NPD3268	Approved
0.6986	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6975	Remote Similarity	NPD6862	Phase 2
0.6974	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6972	Remote Similarity	NPD1669	Approved
0.697	Remote Similarity	NPD1358	Approved
0.6968	Remote Similarity	NPD4123	Phase 3
0.6963	Remote Similarity	NPD7843	Approved
0.6959	Remote Similarity	NPD4618	Approved
0.6959	Remote Similarity	NPD4622	Approved
0.6954	Remote Similarity	NPD1375	Discontinued
0.6951	Remote Similarity	NPD7315	Approved
0.695	Remote Similarity	NPD1535	Discovery
0.6946	Remote Similarity	NPD3965	Phase 1
0.6944	Remote Similarity	NPD3690	Phase 2
0.6944	Remote Similarity	NPD6584	Phase 3
0.6944	Remote Similarity	NPD3691	Phase 2
0.6939	Remote Similarity	NPD4062	Phase 3
0.6939	Remote Similarity	NPD6233	Phase 2
0.6933	Remote Similarity	NPD2799	Discontinued
0.6929	Remote Similarity	NPD2423	Clinical (unspecified phase)
0.6928	Remote Similarity	NPD4628	Phase 3
0.6923	Remote Similarity	NPD2186	Approved
0.6923	Remote Similarity	NPD1876	Approved
0.6918	Remote Similarity	NPD3796	Clinical (unspecified phase)
0.6918	Remote Similarity	NPD5746	Approved
0.6913	Remote Similarity	NPD3052	Approved
0.6913	Remote Similarity	NPD3054	Approved
0.6908	Remote Similarity	NPD2424	Discontinued
0.6901	Remote Similarity	NPD1608	Approved
0.6901	Remote Similarity	NPD3972	Approved
0.6897	Remote Similarity	NPD454	Approved
0.6897	Remote Similarity	NPD9494	Approved
0.6892	Remote Similarity	NPD5837	Clinical (unspecified phase)
0.689	Remote Similarity	NPD2821	Approved
0.6887	Remote Similarity	NPD1537	Approved
0.6887	Remote Similarity	NPD1538	Phase 1
0.6887	Remote Similarity	NPD1519	Approved
0.6884	Remote Similarity	NPD3596	Phase 2
0.6883	Remote Similarity	NPD3692	Discontinued
0.6882	Remote Similarity	NPD7132	Clinical (unspecified phase)
0.6879	Remote Similarity	NPD3496	Discontinued
0.6875	Remote Similarity	NPD5356	Approved
0.6875	Remote Similarity	NPD5355	Approved
0.6871	Remote Similarity	NPD3056	Clinical (unspecified phase)
0.6867	Remote Similarity	NPD5689	Approved
0.6867	Remote Similarity	NPD6894	Phase 1
0.6867	Remote Similarity	NPD5688	Approved
0.6867	Remote Similarity	NPD1536	Approved
0.6863	Remote Similarity	NPD2458	Approved
0.6863	Remote Similarity	NPD2460	Phase 3
0.6863	Remote Similarity	NPD2459	Approved
0.6857	Remote Similarity	NPD2595	Approved
0.6857	Remote Similarity	NPD2594	Approved
0.6855	Remote Similarity	NPD1337	Clinical (unspecified phase)
0.6852	Remote Similarity	NPD7773	Phase 2
0.6849	Remote Similarity	NPD6832	Phase 2
0.6842	Remote Similarity	NPD7546	Discontinued
0.6842	Remote Similarity	NPD2344	Approved
0.6842	Remote Similarity	NPD3656	Approved
0.6842	Remote Similarity	NPD7083	Clinical (unspecified phase)
0.6839	Remote Similarity	NPD6377	Clinical (unspecified phase)
0.6839	Remote Similarity	NPD6666	Approved
0.6839	Remote Similarity	NPD6667	Approved
0.6839	Remote Similarity	NPD3281	Clinical (unspecified phase)
0.6835	Remote Similarity	NPD4003	Phase 3
0.6831	Remote Similarity	NPD1547	Clinical (unspecified phase)
0.6831	Remote Similarity	NPD776	Approved
0.6824	Remote Similarity	NPD2245	Discovery
0.6824	Remote Similarity	NPD1423	Approved
0.6824	Remote Similarity	NPD6104	Discontinued
0.6824	Remote Similarity	NPD1726	Clinical (unspecified phase)
0.6824	Remote Similarity	NPD5729	Clinical (unspecified phase)
0.6821	Remote Similarity	NPD6380	Phase 1
0.6815	Remote Similarity	NPD4319	Phase 2
0.6815	Remote Similarity	NPD6273	Approved
0.6813	Remote Similarity	NPD2366	Approved
0.6812	Remote Similarity	NPD256	Approved
0.6812	Remote Similarity	NPD255	Approved
0.6812	Remote Similarity	NPD7157	Approved
0.681	Remote Similarity	NPD8005	Clinical (unspecified phase)
0.6809	Remote Similarity	NPD1778	Approved
0.6806	Remote Similarity	NPD1283	Approved
0.6805	Remote Similarity	NPD5441	Clinical (unspecified phase)
0.6802	Remote Similarity	NPD6556	Clinical (unspecified phase)
0.68	Remote Similarity	NPD5525	Clinical (unspecified phase)
0.6792	Remote Similarity	NPD3111	Phase 1
0.6792	Remote Similarity	NPD3769	Discontinued
0.6788	Remote Similarity	NPD7485	Phase 3
0.6788	Remote Similarity	NPD7484	Phase 3
0.6786	Remote Similarity	NPD6581	Approved
0.6786	Remote Similarity	NPD6580	Approved
0.6783	Remote Similarity	NPD5108	Clinical (unspecified phase)
0.6783	Remote Similarity	NPD2230	Approved
0.6783	Remote Similarity	NPD2233	Approved
0.6783	Remote Similarity	NPD2232	Approved
0.6782	Remote Similarity	NPD7291	Discontinued
0.6776	Remote Similarity	NPD1523	Approved
0.6776	Remote Similarity	NPD3175	Clinical (unspecified phase)
0.6776	Remote Similarity	NPD7450	Phase 2
0.6776	Remote Similarity	NPD1522	Approved
0.677	Remote Similarity	NPD6844	Discontinued
0.6767	Remote Similarity	NPD968	Approved
0.6761	Remote Similarity	NPD3819	Phase 2

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