NPASS Compound

Structure

NPC476042 OpenBabel07101719152D 22 24 0 0 1 0 0 0 0 0999 V2000 1.7321 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -0.5000 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -0.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 22 1 0 0 0 0 2 4 2 0 0 0 0 2 5 1 0 0 0 0 3 6 2 0 0 0 0 3 7 1 0 0 0 0 4 8 1 0 0 0 0 5 9 2 0 0 0 0 6 10 1 0 0 0 0 7 11 2 0 0 0 0 8 13 2 0 0 0 0 9 13 1 0 0 0 0 10 14 2 0 0 0 0 11 14 1 0 0 0 0 12 15 1 0 0 0 0 12 16 2 0 0 0 0 13 15 1 0 0 0 0 14 17 1 0 0 0 0 15 18 1 0 0 0 0 16 17 1 0 0 0 0 16 22 1 0 0 0 0 17 19 1 0 0 0 0 18 19 1 0 0 0 0 18 20 2 0 0 0 0 19 21 2 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	292.11
Volume:	314.153
LogP:	4.223
LogD:	3.373
LogS:	-4.384
# Rotatable Bonds:	3
TPSA:	49.69
# H-Bond Aceptor:	3
# H-Bond Donor:	2
# Rings:	3
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.702
Synthetic Accessibility Score:	1.864
Fsp3:	0.053
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.945
MDCK Permeability:	1.901664109027479e-05
Pgp-inhibitor:	0.142
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.005
20% Bioavailability (F20%):	0.984
30% Bioavailability (F30%):	0.606

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.2
Plasma Protein Binding (PPB):	100.32626342773438%
Volume Distribution (VD):	0.691
Pgp-substrate:	0.8592545986175537%

ADMET: Metabolism

CYP1A2-inhibitor:	0.96
CYP1A2-substrate:	0.6
CYP2C19-inhibitor:	0.894
CYP2C19-substrate:	0.064
CYP2C9-inhibitor:	0.72
CYP2C9-substrate:	0.833
CYP2D6-inhibitor:	0.087
CYP2D6-substrate:	0.782
CYP3A4-inhibitor:	0.249
CYP3A4-substrate:	0.268

ADMET: Excretion

Clearance (CL):	4.839
Half-life (T1/2):	0.569

ADMET: Toxicity

hERG Blockers:	0.05
Human Hepatotoxicity (H-HT):	0.047
Drug-inuced Liver Injury (DILI):	0.954
AMES Toxicity:	0.216
Rat Oral Acute Toxicity:	0.155
Maximum Recommended Daily Dose:	0.026
Skin Sensitization:	0.77
Carcinogencity:	0.27
Eye Corrosion:	0.003
Eye Irritation:	0.716
Respiratory Toxicity:	0.123

Download Data

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

Natural Product: NPC476042

Natural Product ID:	NPC476042
*Common Name:**	4-Methoxy-3,6-Diphenylcyclohex-4-Ene-1,2-Dione
IUPAC Name:	4-methoxy-3,6-diphenylcyclohex-4-ene-1,2-dione
Synonyms:
Standard InCHIKey:	AXYKUSLHKJFTSV-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C19H16O3/c1-22-16-12-15(13-8-4-2-5-9-13)18(20)19(21)17(16)14-10-6-3-7-11-14/h2-12,15,17H,1H3
SMILES:	COC1=CC(C(=O)C(=O)C1C2=CC=CC=C2)C3=CC=CC=C3
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL523237
PubChem CID:	44583823
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0004603] Organic oxygen compounds [CHEMONTID:0000323] Organooxygen compounds [CHEMONTID:0001831] Carbonyl compounds [CHEMONTID:0000118] Ketones [CHEMONTID:0003487] Cyclic ketones [CHEMONTID:0004325] Cyclohexenones

*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
NPO32661	Phoma sp.	Species	Didymellaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16562839]
NPO32661	Phoma sp.	Species	Didymellaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16643061]
NPO32661	Phoma sp.	Species	Didymellaceae	Eukaryota	giant jellyfish Nemopilema nomurai	n.a.	n.a.	PMID[22483395]
NPO32661	Phoma sp.	Species	Didymellaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26651221]
NPO32661	Phoma sp.	Species	Didymellaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[30785282]
NPO32661	Phoma sp.	Species	Didymellaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[31120749]
NPO32661	Phoma sp.	Species	Didymellaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[7561907]

☑ 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	1

Activity Type	# Activity
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT2	Others	Unspecified		IC50	=	900.0	nM	PMID[508295]

☑ 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 NPC476042 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	243
0.1-0.2	1303
0.2-0.3	2974
0.3-0.4	10068
0.4-0.5	13034
0.5-0.6	12360
0.6-0.7	2449
0.7-0.8	257
0.8-0.85	8
0.85-0.9	0
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.8617	High Similarity	NPC231591
0.8571	High Similarity	NPC103048
0.8485	Intermediate Similarity	NPC145052
0.8469	Intermediate Similarity	NPC12695
0.819	Intermediate Similarity	NPC203732
0.8061	Intermediate Similarity	NPC476484
0.8061	Intermediate Similarity	NPC141607
0.8061	Intermediate Similarity	NPC187725
0.8041	Intermediate Similarity	NPC9822
0.8019	Intermediate Similarity	NPC470007
0.7959	Intermediate Similarity	NPC303967
0.7959	Intermediate Similarity	NPC67585
0.7959	Intermediate Similarity	NPC110420
0.7946	Intermediate Similarity	NPC61651
0.7925	Intermediate Similarity	NPC475905
0.7925	Intermediate Similarity	NPC193640
0.7925	Intermediate Similarity	NPC25385
0.7909	Intermediate Similarity	NPC326664
0.7909	Intermediate Similarity	NPC67377
0.79	Intermediate Similarity	NPC34243
0.7864	Intermediate Similarity	NPC7435
0.783	Intermediate Similarity	NPC471186
0.7822	Intermediate Similarity	NPC206764
0.781	Intermediate Similarity	NPC329556
0.7789	Intermediate Similarity	NPC288903
0.7788	Intermediate Similarity	NPC112552
0.7778	Intermediate Similarity	NPC475282
0.7768	Intermediate Similarity	NPC260886
0.7742	Intermediate Similarity	NPC272260
0.7739	Intermediate Similarity	NPC289432
0.7739	Intermediate Similarity	NPC988
0.7727	Intermediate Similarity	NPC218855
0.7719	Intermediate Similarity	NPC318173
0.7717	Intermediate Similarity	NPC9796
0.7692	Intermediate Similarity	NPC221825
0.7679	Intermediate Similarity	NPC228936
0.7679	Intermediate Similarity	NPC474408
0.7672	Intermediate Similarity	NPC144547
0.767	Intermediate Similarity	NPC226041
0.7664	Intermediate Similarity	NPC134120
0.7664	Intermediate Similarity	NPC474307
0.7658	Intermediate Similarity	NPC469547
0.7658	Intermediate Similarity	NPC477476
0.7658	Intermediate Similarity	NPC477475
0.7653	Intermediate Similarity	NPC322387
0.7632	Intermediate Similarity	NPC471553
0.7632	Intermediate Similarity	NPC268930
0.7629	Intermediate Similarity	NPC294134
0.7627	Intermediate Similarity	NPC325740
0.7619	Intermediate Similarity	NPC158623
0.7611	Intermediate Similarity	NPC135730
0.76	Intermediate Similarity	NPC274455
0.76	Intermediate Similarity	NPC70940
0.76	Intermediate Similarity	NPC84288
0.76	Intermediate Similarity	NPC86670
0.7596	Intermediate Similarity	NPC317280
0.7596	Intermediate Similarity	NPC329387
0.7589	Intermediate Similarity	NPC234637
0.7589	Intermediate Similarity	NPC130591
0.7586	Intermediate Similarity	NPC238861
0.7586	Intermediate Similarity	NPC77000
0.7586	Intermediate Similarity	NPC232958
0.7576	Intermediate Similarity	NPC477693
0.7576	Intermediate Similarity	NPC477704
0.7544	Intermediate Similarity	NPC190298
0.7524	Intermediate Similarity	NPC54647
0.75	Intermediate Similarity	NPC471481
0.75	Intermediate Similarity	NPC328997
0.75	Intermediate Similarity	NPC294050
0.75	Intermediate Similarity	NPC13784
0.75	Intermediate Similarity	NPC143768
0.75	Intermediate Similarity	NPC289201
0.7479	Intermediate Similarity	NPC318067
0.7478	Intermediate Similarity	NPC323440
0.7478	Intermediate Similarity	NPC222968
0.7478	Intermediate Similarity	NPC80605
0.7477	Intermediate Similarity	NPC137315
0.7477	Intermediate Similarity	NPC247976
0.7476	Intermediate Similarity	NPC172925
0.7475	Intermediate Similarity	NPC69057
0.7474	Intermediate Similarity	NPC477703
0.7456	Intermediate Similarity	NPC471616
0.7455	Intermediate Similarity	NPC192577
0.7449	Intermediate Similarity	NPC475710
0.7447	Intermediate Similarity	NPC103488
0.7436	Intermediate Similarity	NPC476225
0.7436	Intermediate Similarity	NPC243059
0.7436	Intermediate Similarity	NPC280827
0.7434	Intermediate Similarity	NPC241851
0.7434	Intermediate Similarity	NPC196075
0.7434	Intermediate Similarity	NPC294458
0.7431	Intermediate Similarity	NPC142326
0.7431	Intermediate Similarity	NPC329705
0.7431	Intermediate Similarity	NPC474111
0.7431	Intermediate Similarity	NPC94751
0.7429	Intermediate Similarity	NPC49994
0.7429	Intermediate Similarity	NPC271475
0.7423	Intermediate Similarity	NPC270507
0.7411	Intermediate Similarity	NPC280789
0.7411	Intermediate Similarity	NPC186128
0.7411	Intermediate Similarity	NPC212415
0.7411	Intermediate Similarity	NPC471188
0.7411	Intermediate Similarity	NPC471189
0.7411	Intermediate Similarity	NPC292834
0.74	Intermediate Similarity	NPC329064
0.7383	Intermediate Similarity	NPC474112
0.7377	Intermediate Similarity	NPC316553
0.7368	Intermediate Similarity	NPC474095
0.7368	Intermediate Similarity	NPC151405
0.7368	Intermediate Similarity	NPC470764
0.7368	Intermediate Similarity	NPC139901
0.7368	Intermediate Similarity	NPC215419
0.7364	Intermediate Similarity	NPC470391
0.7358	Intermediate Similarity	NPC474308
0.7347	Intermediate Similarity	NPC95429
0.7345	Intermediate Similarity	NPC128368
0.7345	Intermediate Similarity	NPC470253
0.7333	Intermediate Similarity	NPC278228
0.7333	Intermediate Similarity	NPC239185
0.7333	Intermediate Similarity	NPC328107
0.7333	Intermediate Similarity	NPC477767
0.7333	Intermediate Similarity	NPC51079
0.7333	Intermediate Similarity	NPC270654
0.7327	Intermediate Similarity	NPC298115
0.7321	Intermediate Similarity	NPC321252
0.7321	Intermediate Similarity	NPC474057
0.7321	Intermediate Similarity	NPC252544
0.7321	Intermediate Similarity	NPC265513
0.732	Intermediate Similarity	NPC323103
0.732	Intermediate Similarity	NPC103387
0.7315	Intermediate Similarity	NPC274443
0.7308	Intermediate Similarity	NPC260233
0.7308	Intermediate Similarity	NPC5472
0.7304	Intermediate Similarity	NPC23402
0.7297	Intermediate Similarity	NPC281604
0.7297	Intermediate Similarity	NPC40178
0.7295	Intermediate Similarity	NPC146239
0.7292	Intermediate Similarity	NPC285716
0.7292	Intermediate Similarity	NPC95868
0.7292	Intermediate Similarity	NPC17408
0.729	Intermediate Similarity	NPC133809
0.729	Intermediate Similarity	NPC128248
0.729	Intermediate Similarity	NPC136810
0.729	Intermediate Similarity	NPC225079
0.7288	Intermediate Similarity	NPC475804
0.7288	Intermediate Similarity	NPC474222
0.7288	Intermediate Similarity	NPC474223
0.7288	Intermediate Similarity	NPC475827
0.7283	Intermediate Similarity	NPC285679
0.7282	Intermediate Similarity	NPC153885
0.7282	Intermediate Similarity	NPC1682
0.7282	Intermediate Similarity	NPC188844
0.7281	Intermediate Similarity	NPC477411
0.7273	Intermediate Similarity	NPC123476
0.7273	Intermediate Similarity	NPC100767
0.7265	Intermediate Similarity	NPC64340
0.7264	Intermediate Similarity	NPC476120
0.7264	Intermediate Similarity	NPC134882
0.7258	Intermediate Similarity	NPC471832
0.7257	Intermediate Similarity	NPC177576
0.7248	Intermediate Similarity	NPC329282
0.7248	Intermediate Similarity	NPC19136
0.7248	Intermediate Similarity	NPC269644
0.7248	Intermediate Similarity	NPC120693
0.7248	Intermediate Similarity	NPC261573
0.7248	Intermediate Similarity	NPC8931
0.7245	Intermediate Similarity	NPC44830
0.7245	Intermediate Similarity	NPC273758
0.7245	Intermediate Similarity	NPC285773
0.7241	Intermediate Similarity	NPC325646
0.7241	Intermediate Similarity	NPC28951
0.7238	Intermediate Similarity	NPC261947
0.7236	Intermediate Similarity	NPC478165
0.7236	Intermediate Similarity	NPC478162
0.7222	Intermediate Similarity	NPC244427
0.7222	Intermediate Similarity	NPC222390
0.7217	Intermediate Similarity	NPC221275
0.7217	Intermediate Similarity	NPC472164
0.7216	Intermediate Similarity	NPC273033
0.7216	Intermediate Similarity	NPC12936
0.7212	Intermediate Similarity	NPC238219
0.7207	Intermediate Similarity	NPC47536
0.7203	Intermediate Similarity	NPC201284
0.7188	Intermediate Similarity	NPC309056
0.7184	Intermediate Similarity	NPC133461
0.7184	Intermediate Similarity	NPC284475
0.7182	Intermediate Similarity	NPC321670
0.7182	Intermediate Similarity	NPC172483
0.7179	Intermediate Similarity	NPC76308
0.7179	Intermediate Similarity	NPC469954
0.7179	Intermediate Similarity	NPC325295
0.7174	Intermediate Similarity	NPC74458
0.717	Intermediate Similarity	NPC156021
0.717	Intermediate Similarity	NPC265220
0.7168	Intermediate Similarity	NPC95126
0.7168	Intermediate Similarity	NPC475002
0.7168	Intermediate Similarity	NPC291799
0.7158	Intermediate Similarity	NPC298023
0.7157	Intermediate Similarity	NPC418308
0.7155	Intermediate Similarity	NPC62138

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 NPC476042 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	243
0.1-0.2	956
0.2-0.3	987
0.3-0.4	3020
0.4-0.5	2500
0.5-0.6	1157
0.6-0.7	250
0.7-0.8	36
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.81	Intermediate Similarity	NPD1989	Approved
0.7864	Intermediate Similarity	NPD2066	Phase 3
0.7835	Intermediate Similarity	NPD1087	Approved
0.781	Intermediate Similarity	NPD1930	Approved
0.781	Intermediate Similarity	NPD1931	Clinical (unspecified phase)
0.781	Intermediate Similarity	NPD1929	Approved
0.7736	Intermediate Similarity	NPD5909	Discontinued
0.7723	Intermediate Similarity	NPD1563	Approved
0.7723	Intermediate Similarity	NPD5122	Clinical (unspecified phase)
0.7647	Intermediate Similarity	NPD1693	Approved
0.76	Intermediate Similarity	NPD3672	Approved
0.76	Intermediate Similarity	NPD1086	Approved
0.76	Intermediate Similarity	NPD1090	Approved
0.76	Intermediate Similarity	NPD1089	Approved
0.76	Intermediate Similarity	NPD3673	Approved
0.7586	Intermediate Similarity	NPD3412	Clinical (unspecified phase)
0.7525	Intermediate Similarity	NPD1239	Approved
0.75	Intermediate Similarity	NPD1564	Approved
0.75	Intermediate Similarity	NPD1565	Approved
0.75	Intermediate Similarity	NPD1566	Phase 3
0.75	Intermediate Similarity	NPD800	Approved
0.7476	Intermediate Similarity	NPD688	Clinical (unspecified phase)
0.7451	Intermediate Similarity	NPD1088	Approved
0.7411	Intermediate Similarity	NPD1609	Clinical (unspecified phase)
0.7383	Intermediate Similarity	NPD1932	Approved
0.7368	Intermediate Similarity	NPD9490	Approved
0.7358	Intermediate Similarity	NPD7798	Approved
0.7345	Intermediate Similarity	NPD6858	Approved
0.7345	Intermediate Similarity	NPD7094	Approved
0.7333	Intermediate Similarity	NPD3495	Discontinued
0.7304	Intermediate Similarity	NPD3317	Approved
0.7297	Intermediate Similarity	NPD2329	Discontinued
0.7295	Intermediate Similarity	NPD2798	Approved
0.7292	Intermediate Similarity	NPD1507	Clinical (unspecified phase)
0.7282	Intermediate Similarity	NPD7631	Approved
0.7263	Intermediate Similarity	NPD225	Approved
0.7263	Intermediate Similarity	NPD227	Approved
0.7245	Intermediate Similarity	NPD9491	Approved
0.7241	Intermediate Similarity	NPD4574	Approved
0.7241	Intermediate Similarity	NPD4576	Approved
0.7216	Intermediate Similarity	NPD942	Approved
0.7184	Intermediate Similarity	NPD7609	Phase 3
0.7168	Intermediate Similarity	NPD4141	Clinical (unspecified phase)
0.7157	Intermediate Similarity	NPD5347	Phase 2
0.7157	Intermediate Similarity	NPD5346	Phase 2
0.713	Intermediate Similarity	NPD2652	Approved
0.713	Intermediate Similarity	NPD2650	Approved
0.7091	Intermediate Similarity	NPD1237	Approved
0.7083	Intermediate Similarity	NPD7457	Clinical (unspecified phase)
0.708	Intermediate Similarity	NPD3646	Clinical (unspecified phase)
0.708	Intermediate Similarity	NPD2067	Discontinued
0.7069	Intermediate Similarity	NPD2629	Approved
0.7059	Intermediate Similarity	NPD1651	Approved
0.7041	Intermediate Similarity	NPD226	Approved
0.7027	Intermediate Similarity	NPD5048	Discontinued
0.7018	Intermediate Similarity	NPD2181	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD2932	Approved
0.6992	Remote Similarity	NPD1876	Approved
0.6981	Remote Similarity	NPD4094	Approved
0.6972	Remote Similarity	NPD3135	Clinical (unspecified phase)
0.6967	Remote Similarity	NPD3972	Approved
0.6967	Remote Similarity	NPD4878	Approved
0.6961	Remote Similarity	NPD4793	Discontinued
0.6961	Remote Similarity	NPD650	Approved
0.6952	Remote Similarity	NPD1508	Approved
0.6942	Remote Similarity	NPD4879	Approved
0.6923	Remote Similarity	NPD5951	Approved
0.6917	Remote Similarity	NPD3025	Approved
0.6917	Remote Similarity	NPD3024	Approved
0.6897	Remote Similarity	NPD2607	Approved
0.6891	Remote Similarity	NPD6065	Approved
0.6887	Remote Similarity	NPD1202	Approved
0.6885	Remote Similarity	NPD1547	Clinical (unspecified phase)
0.6885	Remote Similarity	NPD1281	Approved
0.6881	Remote Similarity	NPD1238	Approved
0.6881	Remote Similarity	NPD3020	Approved
0.686	Remote Similarity	NPD3019	Approved
0.686	Remote Similarity	NPD17	Approved
0.6852	Remote Similarity	NPD4655	Approved
0.6852	Remote Similarity	NPD4657	Approved
0.6842	Remote Similarity	NPD2182	Approved
0.6838	Remote Similarity	NPD1241	Discontinued
0.6833	Remote Similarity	NPD7009	Phase 2
0.6803	Remote Similarity	NPD3026	Approved
0.6803	Remote Similarity	NPD3023	Approved
0.6786	Remote Similarity	NPD164	Approved
0.6783	Remote Similarity	NPD1756	Approved
0.6783	Remote Similarity	NPD4233	Approved
0.6783	Remote Similarity	NPD1752	Approved
0.6783	Remote Similarity	NPD4234	Approved
0.678	Remote Similarity	NPD4766	Approved
0.678	Remote Similarity	NPD1711	Phase 2
0.6759	Remote Similarity	NPD1843	Approved
0.6759	Remote Similarity	NPD5206	Clinical (unspecified phase)
0.6757	Remote Similarity	NPD6027	Approved
0.6757	Remote Similarity	NPD6024	Approved
0.675	Remote Similarity	NPD7610	Discontinued
0.6748	Remote Similarity	NPD2612	Approved
0.6748	Remote Similarity	NPD2610	Approved
0.6748	Remote Similarity	NPD2608	Approved
0.6748	Remote Similarity	NPD4217	Approved
0.6748	Remote Similarity	NPD2611	Approved
0.6748	Remote Similarity	NPD1201	Approved
0.6748	Remote Similarity	NPD2609	Approved
0.6748	Remote Similarity	NPD3131	Approved
0.6748	Remote Similarity	NPD3132	Approved
0.6748	Remote Similarity	NPD6287	Discontinued
0.6748	Remote Similarity	NPD4215	Approved
0.6748	Remote Similarity	NPD4218	Approved
0.6748	Remote Similarity	NPD4216	Approved
0.6742	Remote Similarity	NPD2799	Discontinued
0.6721	Remote Similarity	NPD7163	Clinical (unspecified phase)
0.6721	Remote Similarity	NPD2345	Approved
0.6721	Remote Similarity	NPD5305	Approved
0.6721	Remote Similarity	NPD5306	Approved
0.672	Remote Similarity	NPD1283	Approved
0.6696	Remote Similarity	NPD6647	Phase 2
0.6696	Remote Similarity	NPD6831	Clinical (unspecified phase)
0.6695	Remote Similarity	NPD1370	Approved
0.6695	Remote Similarity	NPD1374	Approved
0.6695	Remote Similarity	NPD1371	Approved
0.6695	Remote Similarity	NPD1373	Approved
0.6694	Remote Similarity	NPD1608	Approved
0.6667	Remote Similarity	NPD5705	Approved
0.6667	Remote Similarity	NPD2313	Discontinued
0.6667	Remote Similarity	NPD3266	Approved
0.6667	Remote Similarity	NPD405	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD1470	Approved
0.6667	Remote Similarity	NPD5704	Approved
0.6667	Remote Similarity	NPD2797	Approved
0.6667	Remote Similarity	NPD5706	Approved
0.6667	Remote Similarity	NPD4136	Approved
0.6667	Remote Similarity	NPD3267	Approved
0.6667	Remote Similarity	NPD4106	Approved
0.6667	Remote Similarity	NPD4135	Approved
0.6667	Remote Similarity	NPD6685	Approved
0.6641	Remote Similarity	NPD4622	Approved
0.6641	Remote Similarity	NPD4618	Approved
0.6639	Remote Similarity	NPD4102	Approved
0.6639	Remote Similarity	NPD5585	Approved
0.6639	Remote Similarity	NPD4105	Approved
0.6639	Remote Similarity	NPD690	Clinical (unspecified phase)
0.6638	Remote Similarity	NPD5235	Approved
0.6638	Remote Similarity	NPD5236	Approved
0.6638	Remote Similarity	NPD5240	Approved
0.6638	Remote Similarity	NPD1317	Discontinued
0.6638	Remote Similarity	NPD5239	Approved
0.6638	Remote Similarity	NPD5237	Approved
0.6636	Remote Similarity	NPD5926	Approved
0.6636	Remote Similarity	NPD9495	Approved
0.6614	Remote Similarity	NPD6085	Phase 2
0.6614	Remote Similarity	NPD5740	Clinical (unspecified phase)
0.6613	Remote Similarity	NPD4807	Approved
0.6613	Remote Similarity	NPD7437	Approved
0.6613	Remote Similarity	NPD4806	Approved
0.6613	Remote Similarity	NPD7436	Approved
0.661	Remote Similarity	NPD1279	Clinical (unspecified phase)
0.6606	Remote Similarity	NPD2860	Approved
0.6606	Remote Similarity	NPD2859	Approved
0.6587	Remote Similarity	NPD5667	Approved
0.6581	Remote Similarity	NPD3644	Approved
0.6581	Remote Similarity	NPD3642	Approved
0.6581	Remote Similarity	NPD3643	Approved
0.6567	Remote Similarity	NPD2796	Approved
0.6565	Remote Similarity	NPD2979	Phase 3
0.6557	Remote Similarity	NPD4479	Discontinued
0.6555	Remote Similarity	NPD5283	Phase 1
0.6555	Remote Similarity	NPD6010	Discontinued
0.6549	Remote Similarity	NPD5700	Clinical (unspecified phase)
0.6549	Remote Similarity	NPD5765	Approved
0.6541	Remote Similarity	NPD5688	Approved
0.6541	Remote Similarity	NPD5689	Approved
0.6538	Remote Similarity	NPD9257	Approved
0.6538	Remote Similarity	NPD9259	Approved
0.6538	Remote Similarity	NPD3268	Approved
0.6519	Remote Similarity	NPD2346	Discontinued
0.6514	Remote Similarity	NPD2934	Approved
0.6514	Remote Similarity	NPD2933	Approved
0.6512	Remote Similarity	NPD6832	Phase 2
0.6508	Remote Similarity	NPD5158	Clinical (unspecified phase)
0.6508	Remote Similarity	NPD5159	Phase 2
0.6508	Remote Similarity	NPD5157	Phase 1
0.6504	Remote Similarity	NPD5981	Approved
0.6496	Remote Similarity	NPD5451	Approved
0.6489	Remote Similarity	NPD8032	Phase 2
0.6484	Remote Similarity	NPD2788	Approved
0.6484	Remote Similarity	NPD6007	Clinical (unspecified phase)
0.6471	Remote Similarity	NPD5535	Approved
0.6462	Remote Similarity	NPD7008	Discontinued
0.6462	Remote Similarity	NPD5952	Clinical (unspecified phase)
0.6462	Remote Similarity	NPD6039	Approved
0.6446	Remote Similarity	NPD4198	Discontinued
0.6435	Remote Similarity	NPD1018	Approved
0.6434	Remote Similarity	NPD7084	Phase 3
0.6423	Remote Similarity	NPD1894	Discontinued
0.6415	Remote Similarity	NPD1101	Approved
0.6415	Remote Similarity	NPD531	Approved
0.6404	Remote Similarity	NPD5738	Clinical (unspecified phase)
0.64	Remote Similarity	NPD3847	Discontinued
0.6397	Remote Similarity	NPD2344	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