NPASS Compound

Structure

NPC473347 OpenBabel07101718272D 21 22 0 0 1 0 0 0 0 0999 V2000 1.5000 2.5981 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0000 -1.7321 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 0.0000 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 -3.4641 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -0.5000 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 -0.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5000 -0.8660 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 -3.4641 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0000 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5000 0.8660 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 -0.0000 -0.0000 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 3.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.0000 1.7321 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -1.7321 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 20 1 0 0 0 0 2 21 1 0 0 0 0 3 4 2 0 0 0 0 3 5 1 0 0 0 0 4 7 1 0 0 0 0 5 8 2 0 0 0 0 6 9 2 0 0 0 0 6 10 1 0 0 0 0 7 13 2 0 0 0 0 8 13 1 0 0 0 0 9 13 1 0 0 0 0 10 17 1 0 0 0 0 11 14 1 0 0 0 0 11 16 2 0 0 0 0 12 15 2 0 0 0 0 12 17 1 0 0 0 0 14 15 1 0 0 0 0 14 18 2 0 0 0 0 15 20 1 0 0 0 0 16 17 1 0 0 0 0 16 21 1 0 0 0 0 17 19 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	286.12
Volume:	302.181
LogP:	1.948
LogD:	2.148
LogS:	-3.788
# Rotatable Bonds:	5
TPSA:	55.76
# H-Bond Aceptor:	4
# H-Bond Donor:	1
# Rings:	2
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.903
Synthetic Accessibility Score:	3.365
Fsp3:	0.235
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:	-4.65
MDCK Permeability:	1.536039235361386e-05
Pgp-inhibitor:	0.659
Pgp-substrate:	0.002
Human Intestinal Absorption (HIA):	0.01
20% Bioavailability (F20%):	0.011
30% Bioavailability (F30%):	0.874

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.765
Plasma Protein Binding (PPB):	94.4719467163086%
Volume Distribution (VD):	0.67
Pgp-substrate:	1.6906503438949585%

ADMET: Metabolism

CYP1A2-inhibitor:	0.97
CYP1A2-substrate:	0.865
CYP2C19-inhibitor:	0.847
CYP2C19-substrate:	0.812
CYP2C9-inhibitor:	0.504
CYP2C9-substrate:	0.254
CYP2D6-inhibitor:	0.259
CYP2D6-substrate:	0.13
CYP3A4-inhibitor:	0.694
CYP3A4-substrate:	0.633

ADMET: Excretion

Clearance (CL):	6.603
Half-life (T1/2):	0.668

ADMET: Toxicity

hERG Blockers:	0.06
Human Hepatotoxicity (H-HT):	0.903
Drug-inuced Liver Injury (DILI):	0.064
AMES Toxicity:	0.467
Rat Oral Acute Toxicity:	0.049
Maximum Recommended Daily Dose:	0.776
Skin Sensitization:	0.944
Carcinogencity:	0.862
Eye Corrosion:	0.008
Eye Irritation:	0.901
Respiratory Toxicity:	0.908

Download Data

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

Natural Product: NPC473347

Natural Product ID:	NPC473347
*Common Name:**	4-Cinnamyl-4-Hydroxy-2,5-Dimethoxycyclohexa-2,5-Dienone
IUPAC Name:	4-hydroxy-2,5-dimethoxy-4-[(E)-3-phenylprop-2-enyl]cyclohexa-2,5-dien-1-one
Synonyms:
Standard InCHIKey:	UJUNVNYVYMHQIS-RMKNXTFCSA-N
Standard InCHI:	InChI=1S/C17H18O4/c1-20-15-12-17(19,16(21-2)11-14(15)18)10-6-9-13-7-4-3-5-8-13/h3-9,11-12,19H,10H2,1-2H3/b9-6+
SMILES:	COC1=CC(=O)C(=CC1(CC=CC2=CC=CC=C2)O)OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL402025
PubChem CID:	24761040
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0002279] Benzene and substituted derivatives [CHEMONTID:0000037] Styrenes

*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
NPO1830	Dalbergia sissoo	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18154272]
NPO1830	Dalbergia sissoo	Species	Fabaceae	Eukaryota	leaves	n.a.	n.a.	PMID[22212722]
NPO1830	Dalbergia sissoo	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO1830	Dalbergia sissoo	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO1830	Dalbergia sissoo	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO1830	Dalbergia sissoo	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

☑ 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
CELL-LINE	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT20763	CELL-LINE	J774.1	Mus musculus	IC50	=	6220.0	nM	PMID[454493]

☑ 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 NPC473347 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	169
0.1-0.2	1258
0.2-0.3	4134
0.3-0.4	12568
0.4-0.5	12973
0.5-0.6	10234
0.6-0.7	1258
0.7-0.8	98
0.8-0.85	3
0.85-0.9	1
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.8557	High Similarity	NPC474308
0.8454	Intermediate Similarity	NPC135951
0.8454	Intermediate Similarity	NPC154517
0.8367	Intermediate Similarity	NPC80115
0.819	Intermediate Similarity	NPC477250
0.8081	Intermediate Similarity	NPC476120
0.8019	Intermediate Similarity	NPC470355
0.798	Intermediate Similarity	NPC278228
0.7979	Intermediate Similarity	NPC194326
0.7917	Intermediate Similarity	NPC108026
0.7818	Intermediate Similarity	NPC108532
0.7732	Intermediate Similarity	NPC303967
0.7732	Intermediate Similarity	NPC67585
0.7732	Intermediate Similarity	NPC110420
0.7723	Intermediate Similarity	NPC145052
0.7723	Intermediate Similarity	NPC179411
0.7653	Intermediate Similarity	NPC472319
0.7653	Intermediate Similarity	NPC476484
0.7624	Intermediate Similarity	NPC103048
0.757	Intermediate Similarity	NPC475282
0.7525	Intermediate Similarity	NPC12695
0.7477	Intermediate Similarity	NPC469509
0.7434	Intermediate Similarity	NPC471553
0.7431	Intermediate Similarity	NPC477247
0.7396	Intermediate Similarity	NPC53299
0.7396	Intermediate Similarity	NPC123476
0.7383	Intermediate Similarity	NPC136962
0.7345	Intermediate Similarity	NPC28951
0.7345	Intermediate Similarity	NPC325646
0.7327	Intermediate Similarity	NPC34243
0.7312	Intermediate Similarity	NPC469894
0.7308	Intermediate Similarity	NPC130193
0.7297	Intermediate Similarity	NPC477245
0.7297	Intermediate Similarity	NPC477246
0.7292	Intermediate Similarity	NPC44546
0.7282	Intermediate Similarity	NPC472788
0.7282	Intermediate Similarity	NPC240042
0.7282	Intermediate Similarity	NPC289201
0.7264	Intermediate Similarity	NPC91820
0.7264	Intermediate Similarity	NPC82426
0.7263	Intermediate Similarity	NPC99240
0.7255	Intermediate Similarity	NPC5472
0.7253	Intermediate Similarity	NPC32203
0.7253	Intermediate Similarity	NPC206800
0.7248	Intermediate Similarity	NPC281604
0.7245	Intermediate Similarity	NPC286608
0.7245	Intermediate Similarity	NPC169050
0.7232	Intermediate Similarity	NPC474641
0.7222	Intermediate Similarity	NPC475203
0.7222	Intermediate Similarity	NPC472315
0.7222	Intermediate Similarity	NPC477251
0.7222	Intermediate Similarity	NPC472316
0.7222	Intermediate Similarity	NPC474376
0.7212	Intermediate Similarity	NPC201967
0.7204	Intermediate Similarity	NPC50192
0.7203	Intermediate Similarity	NPC286573
0.7203	Intermediate Similarity	NPC139171
0.7196	Intermediate Similarity	NPC280616
0.7196	Intermediate Similarity	NPC242913
0.7196	Intermediate Similarity	NPC171831
0.7172	Intermediate Similarity	NPC477704
0.7172	Intermediate Similarity	NPC477693
0.7168	Intermediate Similarity	NPC114144
0.7159	Intermediate Similarity	NPC311343
0.7158	Intermediate Similarity	NPC71795
0.7157	Intermediate Similarity	NPC181709
0.7156	Intermediate Similarity	NPC156648
0.7107	Intermediate Similarity	NPC81135
0.7103	Intermediate Similarity	NPC68269
0.7097	Intermediate Similarity	NPC179726
0.7097	Intermediate Similarity	NPC287790
0.7097	Intermediate Similarity	NPC3672
0.7094	Intermediate Similarity	NPC105709
0.7079	Intermediate Similarity	NPC98880
0.7075	Intermediate Similarity	NPC112552
0.7075	Intermediate Similarity	NPC158623
0.7071	Intermediate Similarity	NPC96625
0.7064	Intermediate Similarity	NPC37115
0.7064	Intermediate Similarity	NPC51174
0.7054	Intermediate Similarity	NPC234376
0.7048	Intermediate Similarity	NPC329387
0.7048	Intermediate Similarity	NPC317280
0.7034	Intermediate Similarity	NPC14007
0.7034	Intermediate Similarity	NPC224814
0.7034	Intermediate Similarity	NPC189844
0.7034	Intermediate Similarity	NPC109083
0.7034	Intermediate Similarity	NPC269843
0.7034	Intermediate Similarity	NPC60962
0.7025	Intermediate Similarity	NPC236405
0.7016	Intermediate Similarity	NPC172673
0.701	Intermediate Similarity	NPC208183
0.701	Intermediate Similarity	NPC324835
0.701	Intermediate Similarity	NPC243289
0.701	Intermediate Similarity	NPC127491
0.701	Intermediate Similarity	NPC308619
0.7	Intermediate Similarity	NPC95289
0.7	Intermediate Similarity	NPC470391
0.7	Intermediate Similarity	NPC471466
0.7	Intermediate Similarity	NPC14141
0.6992	Remote Similarity	NPC110313
0.6991	Remote Similarity	NPC265002
0.699	Remote Similarity	NPC23453
0.6983	Remote Similarity	NPC280001
0.6979	Remote Similarity	NPC303245
0.6979	Remote Similarity	NPC89950
0.6975	Remote Similarity	NPC475328
0.6972	Remote Similarity	NPC127676
0.6964	Remote Similarity	NPC222905
0.6964	Remote Similarity	NPC43584
0.6947	Remote Similarity	NPC78517
0.6947	Remote Similarity	NPC167577
0.6944	Remote Similarity	NPC135784
0.6944	Remote Similarity	NPC160382
0.6937	Remote Similarity	NPC184633
0.6937	Remote Similarity	NPC469511
0.6917	Remote Similarity	NPC65627
0.6916	Remote Similarity	NPC253746
0.6909	Remote Similarity	NPC100767
0.6907	Remote Similarity	NPC283012
0.6907	Remote Similarity	NPC475199
0.6905	Remote Similarity	NPC239302
0.6903	Remote Similarity	NPC292834
0.6903	Remote Similarity	NPC470825
0.6903	Remote Similarity	NPC297657
0.6897	Remote Similarity	NPC268317
0.6893	Remote Similarity	NPC77273
0.6881	Remote Similarity	NPC472222
0.6881	Remote Similarity	NPC472221
0.6881	Remote Similarity	NPC79672
0.6881	Remote Similarity	NPC52087
0.6881	Remote Similarity	NPC249067
0.687	Remote Similarity	NPC217111
0.687	Remote Similarity	NPC93181
0.6869	Remote Similarity	NPC99482
0.6864	Remote Similarity	NPC204784
0.6863	Remote Similarity	NPC26224
0.6863	Remote Similarity	NPC213156
0.6863	Remote Similarity	NPC240108
0.686	Remote Similarity	NPC160900
0.686	Remote Similarity	NPC18984
0.686	Remote Similarity	NPC229084
0.686	Remote Similarity	NPC106659
0.6857	Remote Similarity	NPC286006
0.6857	Remote Similarity	NPC30361
0.6852	Remote Similarity	NPC472585
0.6852	Remote Similarity	NPC244427
0.6852	Remote Similarity	NPC94343
0.6852	Remote Similarity	NPC222390
0.6847	Remote Similarity	NPC260952
0.6847	Remote Similarity	NPC277788
0.6847	Remote Similarity	NPC20485
0.6842	Remote Similarity	NPC176228
0.6842	Remote Similarity	NPC51698
0.6842	Remote Similarity	NPC48525
0.6822	Remote Similarity	NPC54647
0.6818	Remote Similarity	NPC472919
0.6814	Remote Similarity	NPC133308
0.6814	Remote Similarity	NPC21162
0.6814	Remote Similarity	NPC471535
0.6814	Remote Similarity	NPC183700
0.6814	Remote Similarity	NPC291799
0.681	Remote Similarity	NPC471616
0.681	Remote Similarity	NPC23402
0.681	Remote Similarity	NPC216387
0.6804	Remote Similarity	NPC242628
0.6804	Remote Similarity	NPC133050
0.6803	Remote Similarity	NPC474803
0.6803	Remote Similarity	NPC474766
0.68	Remote Similarity	NPC253595
0.68	Remote Similarity	NPC474211
0.6792	Remote Similarity	NPC156021
0.6792	Remote Similarity	NPC133135
0.6792	Remote Similarity	NPC283711
0.6792	Remote Similarity	NPC251579
0.6789	Remote Similarity	NPC274443
0.6789	Remote Similarity	NPC304638
0.6786	Remote Similarity	NPC182549
0.6786	Remote Similarity	NPC114741
0.6783	Remote Similarity	NPC11824
0.6783	Remote Similarity	NPC474363
0.6778	Remote Similarity	NPC82770
0.6778	Remote Similarity	NPC78954
0.6778	Remote Similarity	NPC239931
0.6777	Remote Similarity	NPC164947
0.6771	Remote Similarity	NPC151405
0.6771	Remote Similarity	NPC139901
0.6768	Remote Similarity	NPC304538
0.6765	Remote Similarity	NPC1793
0.6762	Remote Similarity	NPC81010
0.6762	Remote Similarity	NPC32977
0.6762	Remote Similarity	NPC206764
0.6757	Remote Similarity	NPC69332
0.6757	Remote Similarity	NPC95178
0.6757	Remote Similarity	NPC70843
0.6757	Remote Similarity	NPC29989
0.6754	Remote Similarity	NPC226250
0.6754	Remote Similarity	NPC474314
0.6752	Remote Similarity	NPC281277
0.6752	Remote Similarity	NPC19290
0.675	Remote Similarity	NPC158949

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 NPC473347 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	156
0.1-0.2	886
0.2-0.3	1466
0.3-0.4	3363
0.4-0.5	2365
0.5-0.6	839
0.6-0.7	71
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
0.7321	Intermediate Similarity	NPD690	Clinical (unspecified phase)
0.7253	Intermediate Similarity	NPD9716	Approved
0.7245	Intermediate Similarity	NPD1282	Approved
0.7188	Intermediate Similarity	NPD3971	Phase 1
0.7103	Intermediate Similarity	NPD6647	Phase 2
0.7027	Intermediate Similarity	NPD2067	Discontinued
0.699	Remote Similarity	NPD5122	Clinical (unspecified phase)
0.6957	Remote Similarity	NPD4198	Discontinued
0.6881	Remote Similarity	NPD1237	Approved
0.6869	Remote Similarity	NPD5734	Clinical (unspecified phase)
0.686	Remote Similarity	NPD4379	Clinical (unspecified phase)
0.6814	Remote Similarity	NPD4141	Clinical (unspecified phase)
0.6765	Remote Similarity	NPD689	Discontinued
0.6754	Remote Similarity	NPD969	Suspended
0.6729	Remote Similarity	NPD9495	Approved
0.6727	Remote Similarity	NPD5909	Discontinued
0.6724	Remote Similarity	NPD2629	Approved
0.6696	Remote Similarity	NPD1358	Approved
0.6667	Remote Similarity	NPD2066	Phase 3
0.6637	Remote Similarity	NPD6831	Clinical (unspecified phase)
0.661	Remote Similarity	NPD694	Clinical (unspecified phase)
0.6604	Remote Similarity	NPD2934	Approved
0.6604	Remote Similarity	NPD2933	Approved
0.6562	Remote Similarity	NPD9294	Approved
0.6555	Remote Similarity	NPD5536	Phase 2
0.6542	Remote Similarity	NPD2860	Approved
0.6542	Remote Similarity	NPD2859	Approved
0.6529	Remote Similarity	NPD5305	Approved
0.6529	Remote Similarity	NPD5306	Approved
0.6518	Remote Similarity	NPD5048	Discontinued
0.6476	Remote Similarity	NPD7609	Phase 3
0.6475	Remote Similarity	NPD4106	Approved
0.6475	Remote Similarity	NPD4135	Approved
0.6475	Remote Similarity	NPD4136	Approved
0.646	Remote Similarity	NPD3134	Approved
0.6449	Remote Similarity	NPD6048	Clinical (unspecified phase)
0.6449	Remote Similarity	NPD6049	Phase 2
0.6446	Remote Similarity	NPD4105	Approved
0.6446	Remote Similarity	NPD4102	Approved
0.6423	Remote Similarity	NPD4807	Approved
0.6423	Remote Similarity	NPD4806	Approved
0.6415	Remote Similarity	NPD7631	Approved
0.6408	Remote Similarity	NPD650	Approved
0.6381	Remote Similarity	NPD9258	Approved
0.6381	Remote Similarity	NPD9256	Approved
0.6373	Remote Similarity	NPD111	Approved
0.6364	Remote Similarity	NPD3020	Approved
0.6348	Remote Similarity	NPD2684	Approved
0.6339	Remote Similarity	NPD1930	Approved
0.6339	Remote Similarity	NPD1931	Clinical (unspecified phase)
0.6339	Remote Similarity	NPD5738	Clinical (unspecified phase)
0.6339	Remote Similarity	NPD1929	Approved
0.6325	Remote Similarity	NPD1609	Clinical (unspecified phase)
0.63	Remote Similarity	NPD942	Approved
0.6293	Remote Similarity	NPD3021	Approved
0.6293	Remote Similarity	NPD3022	Approved
0.6279	Remote Similarity	NPD7095	Approved
0.6273	Remote Similarity	NPD5926	Approved
0.6271	Remote Similarity	NPD7843	Approved
0.6261	Remote Similarity	NPD290	Approved
0.6261	Remote Similarity	NPD5979	Clinical (unspecified phase)
0.626	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.626	Remote Similarity	NPD4060	Phase 1
0.6231	Remote Similarity	NPD6798	Discontinued
0.6218	Remote Similarity	NPD1241	Discontinued
0.6212	Remote Similarity	NPD4340	Discontinued
0.6204	Remote Similarity	NPD1202	Approved
0.6204	Remote Similarity	NPD845	Approved
0.62	Remote Similarity	NPD1507	Clinical (unspecified phase)
0.6186	Remote Similarity	NPD228	Approved
0.6183	Remote Similarity	NPD6233	Phase 2
0.6183	Remote Similarity	NPD4062	Phase 3
0.6182	Remote Similarity	NPD3495	Discontinued
0.6176	Remote Similarity	NPD9491	Approved
0.6147	Remote Similarity	NPD1432	Clinical (unspecified phase)
0.6147	Remote Similarity	NPD1693	Approved
0.6139	Remote Similarity	NPD226	Approved
0.6132	Remote Similarity	NPD5347	Phase 2
0.6132	Remote Similarity	NPD800	Approved
0.6132	Remote Similarity	NPD5346	Phase 2
0.6124	Remote Similarity	NPD5204	Approved
0.6116	Remote Similarity	NPD7157	Approved
0.6106	Remote Similarity	NPD4817	Approved
0.6106	Remote Similarity	NPD4818	Approved
0.6106	Remote Similarity	NPD1932	Approved
0.6095	Remote Similarity	NPD4793	Discontinued
0.6094	Remote Similarity	NPD2625	Approved
0.6094	Remote Similarity	NPD2628	Approved
0.6094	Remote Similarity	NPD2627	Approved
0.6094	Remote Similarity	NPD2626	Approved
0.6094	Remote Similarity	NPD2160	Approved
0.6094	Remote Similarity	NPD2159	Approved
0.6091	Remote Similarity	NPD844	Approved
0.609	Remote Similarity	NPD6355	Discontinued
0.6083	Remote Similarity	NPD4869	Clinical (unspecified phase)
0.608	Remote Similarity	NPD3496	Discontinued
0.6077	Remote Similarity	NPD5202	Clinical (unspecified phase)
0.6077	Remote Similarity	NPD4620	Approved
0.6077	Remote Similarity	NPD5201	Approved
0.6077	Remote Similarity	NPD5203	Approved
0.6077	Remote Similarity	NPD4617	Approved
0.6075	Remote Similarity	NPD1090	Approved
0.6075	Remote Similarity	NPD1086	Approved
0.6075	Remote Similarity	NPD1089	Approved
0.6071	Remote Similarity	NPD7798	Approved
0.6071	Remote Similarity	NPD1238	Approved
0.6068	Remote Similarity	NPD2182	Approved
0.6066	Remote Similarity	NPD9493	Approved
0.6053	Remote Similarity	NPD5700	Clinical (unspecified phase)
0.6047	Remote Similarity	NPD6007	Clinical (unspecified phase)
0.6047	Remote Similarity	NPD2788	Approved
0.6043	Remote Similarity	NPD6190	Approved
0.6043	Remote Similarity	NPD2354	Approved
0.6034	Remote Similarity	NPD968	Approved
0.6033	Remote Similarity	NPD5951	Approved
0.6031	Remote Similarity	NPD5952	Clinical (unspecified phase)
0.6019	Remote Similarity	NPD1007	Discontinued
0.6018	Remote Similarity	NPD3028	Approved
0.6	Remote Similarity	NPD5277	Phase 2
0.6	Remote Similarity	NPD4626	Approved
0.6	Remote Similarity	NPD9494	Approved
0.6	Remote Similarity	NPD9259	Approved
0.6	Remote Similarity	NPD3664	Approved
0.6	Remote Similarity	NPD3663	Approved
0.6	Remote Similarity	NPD9257	Approved
0.6	Remote Similarity	NPD3662	Phase 3
0.6	Remote Similarity	NPD164	Approved
0.6	Remote Similarity	NPD3661	Approved
0.5986	Remote Similarity	NPD5049	Phase 3
0.5985	Remote Similarity	NPD1048	Approved
0.5985	Remote Similarity	NPD4621	Approved
0.5985	Remote Similarity	NPD4619	Approved
0.5984	Remote Similarity	NPD4878	Approved
0.5984	Remote Similarity	NPD6671	Approved
0.5983	Remote Similarity	NPD9532	Phase 3
0.5983	Remote Similarity	NPD6406	Approved
0.5969	Remote Similarity	NPD987	Approved
0.5968	Remote Similarity	NPD9545	Approved
0.5966	Remote Similarity	NPD2181	Clinical (unspecified phase)
0.5965	Remote Similarity	NPD846	Approved
0.5965	Remote Similarity	NPD940	Approved
0.5963	Remote Similarity	NPD1088	Approved
0.5963	Remote Similarity	NPD159	Clinical (unspecified phase)
0.5957	Remote Similarity	NPD6799	Approved
0.5952	Remote Similarity	NPD4879	Approved
0.5952	Remote Similarity	NPD3847	Discontinued
0.595	Remote Similarity	NPD6010	Discontinued
0.595	Remote Similarity	NPD5283	Phase 1
0.5948	Remote Similarity	NPD9697	Approved
0.5946	Remote Similarity	NPD1989	Approved
0.5946	Remote Similarity	NPD1809	Phase 2
0.5943	Remote Similarity	NPD506	Clinical (unspecified phase)
0.5942	Remote Similarity	NPD2424	Discontinued
0.594	Remote Similarity	NPD4248	Discontinued
0.5938	Remote Similarity	NPD5157	Phase 1
0.5938	Remote Similarity	NPD5158	Clinical (unspecified phase)
0.5938	Remote Similarity	NPD5159	Phase 2
0.5935	Remote Similarity	NPD405	Clinical (unspecified phase)
0.5932	Remote Similarity	NPD2329	Discontinued
0.5926	Remote Similarity	NPD3672	Approved
0.5926	Remote Similarity	NPD3673	Approved
0.5923	Remote Similarity	NPD5647	Approved
0.592	Remote Similarity	NPD4196	Clinical (unspecified phase)
0.5913	Remote Similarity	NPD4231	Approved
0.5913	Remote Similarity	NPD4658	Approved
0.5913	Remote Similarity	NPD3682	Approved
0.5913	Remote Similarity	NPD3683	Approved
0.5913	Remote Similarity	NPD4229	Approved
0.5913	Remote Similarity	NPD3680	Approved
0.5913	Remote Similarity	NPD3681	Approved
0.5913	Remote Similarity	NPD4656	Approved
0.5909	Remote Similarity	NPD1066	Discontinued
0.5906	Remote Similarity	NPD1091	Approved
0.59	Remote Similarity	NPD4756	Discovery
0.5897	Remote Similarity	NPD6685	Approved
0.5896	Remote Similarity	NPD5121	Approved
0.5896	Remote Similarity	NPD5120	Approved
0.5896	Remote Similarity	NPD5119	Approved
0.5893	Remote Similarity	NPD288	Approved
0.5888	Remote Similarity	NPD1101	Approved
0.5888	Remote Similarity	NPD531	Approved
0.5882	Remote Similarity	NPD4750	Phase 3
0.5882	Remote Similarity	NPD1317	Discontinued
0.5877	Remote Similarity	NPD1616	Discontinued
0.5877	Remote Similarity	NPD289	Clinical (unspecified phase)
0.5877	Remote Similarity	NPD3135	Clinical (unspecified phase)
0.5877	Remote Similarity	NPD1242	Phase 1
0.5873	Remote Similarity	NPD5126	Approved
0.5873	Remote Similarity	NPD5125	Phase 3
0.5873	Remote Similarity	NPD7163	Clinical (unspecified phase)
0.5873	Remote Similarity	NPD2932	Approved
0.5873	Remote Similarity	NPD3412	Clinical (unspecified phase)
0.5872	Remote Similarity	NPD1239	Approved
0.587	Remote Similarity	NPD7266	Discontinued
0.587	Remote Similarity	NPD5763	Approved
0.587	Remote Similarity	NPD5762	Approved
0.5868	Remote Similarity	NPD5535	Approved
0.5865	Remote Similarity	NPD3268	Approved
0.5859	Remote Similarity	NPD3972	Approved
0.5859	Remote Similarity	NPD9717	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