NPASS Compound

Structure

NPC179411 OpenBabel07101719512D 22 23 0 0 1 0 0 0 0 0999 V2000 1.7321 -4.0000 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 5.1962 0.0000 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 -1.7321 -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 3.4641 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 C 0 0 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 2.5981 0.5000 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 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 0.0000 -1.0000 0.0000 C 0 0 2 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 0.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -2.5000 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 -0.8660 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 22 1 0 0 0 0 2 3 2 0 0 0 0 2 4 1 0 0 0 0 3 6 1 0 0 0 0 4 7 2 0 0 0 0 5 8 1 0 0 0 0 5 9 2 0 0 0 0 6 13 2 0 0 0 0 7 13 1 0 0 0 0 8 14 1 0 0 0 0 9 15 1 0 0 0 0 10 11 2 0 0 0 0 10 13 1 0 0 0 0 11 16 1 0 0 0 0 12 17 1 0 0 0 0 14 12 1 1 0 0 0 14 18 1 0 0 0 0 15 18 1 0 0 0 0 15 19 2 0 0 0 0 16 18 2 0 0 0 0 16 20 1 0 0 0 0 17 21 2 0 0 0 0 17 22 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	298.12
Volume:	316.841
LogP:	2.375
LogD:	1.153
LogS:	-3.586
# Rotatable Bonds:	6
TPSA:	60.44
# H-Bond Aceptor:	4
# H-Bond Donor:	0
# Rings:	2
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.363
Synthetic Accessibility Score:	3.521
Fsp3:	0.278
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	2
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.602
MDCK Permeability:	2.8302336431806907e-05
Pgp-inhibitor:	0.002
Pgp-substrate:	0.005
Human Intestinal Absorption (HIA):	0.016
20% Bioavailability (F20%):	0.002
30% Bioavailability (F30%):	0.014

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.938
Plasma Protein Binding (PPB):	87.8560562133789%
Volume Distribution (VD):	0.249
Pgp-substrate:	11.944249153137207%

ADMET: Metabolism

CYP1A2-inhibitor:	0.59
CYP1A2-substrate:	0.385
CYP2C19-inhibitor:	0.17
CYP2C19-substrate:	0.116
CYP2C9-inhibitor:	0.189
CYP2C9-substrate:	0.359
CYP2D6-inhibitor:	0.013
CYP2D6-substrate:	0.187
CYP3A4-inhibitor:	0.532
CYP3A4-substrate:	0.247

ADMET: Excretion

Clearance (CL):	12.269
Half-life (T1/2):	0.833

ADMET: Toxicity

hERG Blockers:	0.018
Human Hepatotoxicity (H-HT):	0.086
Drug-inuced Liver Injury (DILI):	0.438
AMES Toxicity:	0.057
Rat Oral Acute Toxicity:	0.359
Maximum Recommended Daily Dose:	0.036
Skin Sensitization:	0.693
Carcinogencity:	0.84
Eye Corrosion:	0.66
Eye Irritation:	0.765
Respiratory Toxicity:	0.416

Download Data

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

Natural Product: NPC179411

Natural Product ID:	NPC179411
*Common Name:**	Infectocaryone
IUPAC Name:	methyl 2-[(1R,6Z)-6-[(E)-1-hydroxy-3-phenylprop-2-enylidene]-5-oxocyclohex-3-en-1-yl]acetate
Synonyms:	Infectocaryone
Standard InCHIKey:	HAXYQNFQUDHACW-LVJWOEPNSA-N
Standard InCHI:	InChI=1S/C18H18O4/c1-22-17(21)12-14-8-5-9-15(19)18(14)16(20)11-10-13-6-3-2-4-7-13/h2-7,9-11,14,20H,8,12H2,1H3/b11-10+,18-16-/t14-/m1/s1
SMILES:	COC(=O)C[C@H]1CC=CC(=O)/C/1=C(/C=C/c1ccccc1)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1223794
PubChem CID:	10379922
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:0000125] Quinomethanes [CHEMONTID:0002122] O-quinomethanes

*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
NPO15311	Cryptocarya chinensis	Species	Lauraceae	Eukaryota	leaves	Lai-I, Pingtung County, Taiwan	2005-May	PMID[20704331]
NPO15311	Cryptocarya chinensis	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO15311	Cryptocarya chinensis	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO15311	Cryptocarya chinensis	Species	Lauraceae	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	4

Activity Type	# Activity
Cell Line	4

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT83	Cell Line	MCF7	Homo sapiens	IC50	=	24300.0	nM	PMID[533787]
NPT397	Cell Line	NCI-H460	Homo sapiens	IC50	=	11000.0	nM	PMID[533787]
NPT395	Cell Line	SF-268	Homo sapiens	IC50	=	3700.0	nM	PMID[533787]
NPT91	Cell Line	KB	Homo sapiens	IC50	=	1700.0	nM	PMID[533787]

☑ 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 NPC179411 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	181
0.1-0.2	962
0.2-0.3	3048
0.3-0.4	9617
0.4-0.5	14484
0.5-0.6	11831
0.6-0.7	2295
0.7-0.8	269
0.8-0.85	5
0.85-0.9	3
0.9-0.95	0
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.89	High Similarity	NPC51174
0.866	High Similarity	NPC278228
0.8571	High Similarity	NPC476120
0.83	Intermediate Similarity	NPC474308
0.8131	Intermediate Similarity	NPC474689
0.8105	Intermediate Similarity	NPC194326
0.8021	Intermediate Similarity	NPC477693
0.8021	Intermediate Similarity	NPC477704
0.7941	Intermediate Similarity	NPC54647
0.7925	Intermediate Similarity	NPC20485
0.7895	Intermediate Similarity	NPC123476
0.785	Intermediate Similarity	NPC475282
0.7843	Intermediate Similarity	NPC145052
0.7843	Intermediate Similarity	NPC317280
0.7843	Intermediate Similarity	NPC329387
0.781	Intermediate Similarity	NPC329282
0.7807	Intermediate Similarity	NPC474223
0.7807	Intermediate Similarity	NPC474222
0.7807	Intermediate Similarity	NPC475804
0.7807	Intermediate Similarity	NPC475827
0.7757	Intermediate Similarity	NPC47536
0.7745	Intermediate Similarity	NPC289201
0.7723	Intermediate Similarity	NPC473347
0.7714	Intermediate Similarity	NPC301943
0.7714	Intermediate Similarity	NPC474365
0.7708	Intermediate Similarity	NPC53299
0.77	Intermediate Similarity	NPC77273
0.7685	Intermediate Similarity	NPC281604
0.7685	Intermediate Similarity	NPC469511
0.7685	Intermediate Similarity	NPC40178
0.7664	Intermediate Similarity	NPC477251
0.7658	Intermediate Similarity	NPC294458
0.7607	Intermediate Similarity	NPC474159
0.7607	Intermediate Similarity	NPC474254
0.7604	Intermediate Similarity	NPC44546
0.76	Intermediate Similarity	NPC476484
0.7582	Intermediate Similarity	NPC32203
0.7582	Intermediate Similarity	NPC206800
0.7573	Intermediate Similarity	NPC103048
0.7565	Intermediate Similarity	NPC204784
0.7551	Intermediate Similarity	NPC96625
0.7542	Intermediate Similarity	NPC85511
0.7527	Intermediate Similarity	NPC50192
0.75	Intermediate Similarity	NPC110420
0.75	Intermediate Similarity	NPC243059
0.75	Intermediate Similarity	NPC67585
0.75	Intermediate Similarity	NPC244933
0.75	Intermediate Similarity	NPC303967
0.75	Intermediate Similarity	NPC85560
0.75	Intermediate Similarity	NPC44830
0.75	Intermediate Similarity	NPC280827
0.7477	Intermediate Similarity	NPC280789
0.7476	Intermediate Similarity	NPC12695
0.7474	Intermediate Similarity	NPC303245
0.7456	Intermediate Similarity	NPC190298
0.7453	Intermediate Similarity	NPC284477
0.7453	Intermediate Similarity	NPC25458
0.7451	Intermediate Similarity	NPC34243
0.7431	Intermediate Similarity	NPC156648
0.7429	Intermediate Similarity	NPC228435
0.7429	Intermediate Similarity	NPC325497
0.7429	Intermediate Similarity	NPC146351
0.7419	Intermediate Similarity	NPC3672
0.7419	Intermediate Similarity	NPC287790
0.7411	Intermediate Similarity	NPC93287
0.7411	Intermediate Similarity	NPC306977
0.7411	Intermediate Similarity	NPC477475
0.7411	Intermediate Similarity	NPC287055
0.7411	Intermediate Similarity	NPC477476
0.7411	Intermediate Similarity	NPC242957
0.7411	Intermediate Similarity	NPC471481
0.7411	Intermediate Similarity	NPC206414
0.7407	Intermediate Similarity	NPC321670
0.7404	Intermediate Similarity	NPC253423
0.7404	Intermediate Similarity	NPC477767
0.7404	Intermediate Similarity	NPC240042
0.7396	Intermediate Similarity	NPC99240
0.7387	Intermediate Similarity	NPC476003
0.7387	Intermediate Similarity	NPC222905
0.7383	Intermediate Similarity	NPC329556
0.7379	Intermediate Similarity	NPC206764
0.7379	Intermediate Similarity	NPC130398
0.7373	Intermediate Similarity	NPC269923
0.7373	Intermediate Similarity	NPC167323
0.7368	Intermediate Similarity	NPC127343
0.7347	Intermediate Similarity	NPC95965
0.7345	Intermediate Similarity	NPC153053
0.7345	Intermediate Similarity	NPC234637
0.7345	Intermediate Similarity	NPC130591
0.7345	Intermediate Similarity	NPC471721
0.7333	Intermediate Similarity	NPC229242
0.7333	Intermediate Similarity	NPC35448
0.7333	Intermediate Similarity	NPC135951
0.7333	Intermediate Similarity	NPC154517
0.7333	Intermediate Similarity	NPC271475
0.7333	Intermediate Similarity	NPC225060
0.7333	Intermediate Similarity	NPC78701
0.7327	Intermediate Similarity	NPC62765
0.7327	Intermediate Similarity	NPC240108
0.7327	Intermediate Similarity	NPC26224
0.7327	Intermediate Similarity	NPC213156
0.7327	Intermediate Similarity	NPC84288
0.732	Intermediate Similarity	NPC288903
0.732	Intermediate Similarity	NPC270507
0.732	Intermediate Similarity	NPC243289
0.732	Intermediate Similarity	NPC208183
0.7308	Intermediate Similarity	NPC61944
0.7308	Intermediate Similarity	NPC469893
0.7304	Intermediate Similarity	NPC28951
0.7304	Intermediate Similarity	NPC325646
0.7304	Intermediate Similarity	NPC108532
0.7292	Intermediate Similarity	NPC71795
0.7292	Intermediate Similarity	NPC89950
0.729	Intermediate Similarity	NPC304873
0.7282	Intermediate Similarity	NPC261181
0.7282	Intermediate Similarity	NPC23453
0.7281	Intermediate Similarity	NPC114144
0.7281	Intermediate Similarity	NPC217111
0.7281	Intermediate Similarity	NPC210092
0.7273	Intermediate Similarity	NPC470007
0.7264	Intermediate Similarity	NPC217621
0.7264	Intermediate Similarity	NPC203925
0.7264	Intermediate Similarity	NPC80115
0.7263	Intermediate Similarity	NPC78517
0.7263	Intermediate Similarity	NPC151405
0.7263	Intermediate Similarity	NPC139901
0.7263	Intermediate Similarity	NPC167577
0.7257	Intermediate Similarity	NPC272524
0.7255	Intermediate Similarity	NPC110704
0.725	Intermediate Similarity	NPC140118
0.725	Intermediate Similarity	NPC12881
0.7248	Intermediate Similarity	NPC269457
0.7241	Intermediate Similarity	NPC152812
0.7238	Intermediate Similarity	NPC469892
0.7238	Intermediate Similarity	NPC469890
0.7238	Intermediate Similarity	NPC133135
0.7238	Intermediate Similarity	NPC270654
0.7238	Intermediate Similarity	NPC249912
0.7238	Intermediate Similarity	NPC276775
0.7238	Intermediate Similarity	NPC92754
0.7238	Intermediate Similarity	NPC251579
0.7238	Intermediate Similarity	NPC469891
0.7234	Intermediate Similarity	NPC179726
0.7228	Intermediate Similarity	NPC9822
0.7228	Intermediate Similarity	NPC231591
0.7228	Intermediate Similarity	NPC173443
0.7228	Intermediate Similarity	NPC220893
0.7222	Intermediate Similarity	NPC68269
0.7222	Intermediate Similarity	NPC247976
0.7217	Intermediate Similarity	NPC23402
0.7217	Intermediate Similarity	NPC471616
0.7216	Intermediate Similarity	NPC103387
0.7216	Intermediate Similarity	NPC323103
0.7212	Intermediate Similarity	NPC5472
0.7207	Intermediate Similarity	NPC474364
0.7207	Intermediate Similarity	NPC85493
0.7207	Intermediate Similarity	NPC469636
0.7207	Intermediate Similarity	NPC182549
0.7207	Intermediate Similarity	NPC114741
0.7207	Intermediate Similarity	NPC31274
0.72	Intermediate Similarity	NPC169050
0.72	Intermediate Similarity	NPC286608
0.72	Intermediate Similarity	NPC322387
0.7196	Intermediate Similarity	NPC112552
0.7196	Intermediate Similarity	NPC253746
0.7193	Intermediate Similarity	NPC474363
0.7193	Intermediate Similarity	NPC87069
0.719	Intermediate Similarity	NPC295664
0.7188	Intermediate Similarity	NPC477703
0.7182	Intermediate Similarity	NPC136962
0.7182	Intermediate Similarity	NPC69332
0.7182	Intermediate Similarity	NPC100767
0.7182	Intermediate Similarity	NPC70843
0.7182	Intermediate Similarity	NPC29989
0.7182	Intermediate Similarity	NPC95178
0.7172	Intermediate Similarity	NPC475710
0.7172	Intermediate Similarity	NPC294134
0.717	Intermediate Similarity	NPC120393
0.7168	Intermediate Similarity	NPC218855
0.7168	Intermediate Similarity	NPC228609
0.7168	Intermediate Similarity	NPC321852
0.7168	Intermediate Similarity	NPC292834
0.7168	Intermediate Similarity	NPC477250
0.7168	Intermediate Similarity	NPC474314
0.7158	Intermediate Similarity	NPC176228
0.7157	Intermediate Similarity	NPC86670
0.7157	Intermediate Similarity	NPC70940
0.7157	Intermediate Similarity	NPC108026
0.7157	Intermediate Similarity	NPC274455
0.7156	Intermediate Similarity	NPC269644
0.7156	Intermediate Similarity	NPC472222
0.7156	Intermediate Similarity	NPC472221
0.7155	Intermediate Similarity	NPC158157
0.7143	Intermediate Similarity	NPC308619
0.7143	Intermediate Similarity	NPC127491
0.7143	Intermediate Similarity	NPC285773
0.7143	Intermediate Similarity	NPC88141
0.7143	Intermediate Similarity	NPC196246
0.7143	Intermediate Similarity	NPC214067
0.7143	Intermediate Similarity	NPC324835

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 NPC179411 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	160
0.1-0.2	759
0.2-0.3	1399
0.3-0.4	3033
0.4-0.5	2523
0.5-0.6	1067
0.6-0.7	175
0.7-0.8	32
0.8-0.85	2
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8351	Intermediate Similarity	NPD5122	Clinical (unspecified phase)
0.8235	Intermediate Similarity	NPD6647	Phase 2
0.7981	Intermediate Similarity	NPD5909	Discontinued
0.7767	Intermediate Similarity	NPD2066	Phase 3
0.7736	Intermediate Similarity	NPD5048	Discontinued
0.7582	Intermediate Similarity	NPD9716	Approved
0.7523	Intermediate Similarity	NPD6831	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD3971	Phase 1
0.74	Intermediate Similarity	NPD5346	Phase 2
0.74	Intermediate Similarity	NPD5347	Phase 2
0.7383	Intermediate Similarity	NPD1929	Approved
0.7383	Intermediate Similarity	NPD1930	Approved
0.7383	Intermediate Similarity	NPD1931	Clinical (unspecified phase)
0.7327	Intermediate Similarity	NPD3672	Approved
0.7327	Intermediate Similarity	NPD9258	Approved
0.7327	Intermediate Similarity	NPD9256	Approved
0.7327	Intermediate Similarity	NPD3673	Approved
0.7292	Intermediate Similarity	NPD226	Approved
0.7282	Intermediate Similarity	NPD1202	Approved
0.7228	Intermediate Similarity	NPD800	Approved
0.7222	Intermediate Similarity	NPD5738	Clinical (unspecified phase)
0.7212	Intermediate Similarity	NPD1693	Approved
0.72	Intermediate Similarity	NPD4793	Discontinued
0.72	Intermediate Similarity	NPD1282	Approved
0.7172	Intermediate Similarity	NPD5734	Clinical (unspecified phase)
0.717	Intermediate Similarity	NPD5926	Approved
0.7158	Intermediate Similarity	NPD227	Approved
0.7158	Intermediate Similarity	NPD225	Approved
0.7157	Intermediate Similarity	NPD1090	Approved
0.7157	Intermediate Similarity	NPD1086	Approved
0.7157	Intermediate Similarity	NPD1089	Approved
0.7143	Intermediate Similarity	NPD9491	Approved
0.7143	Intermediate Similarity	NPD2067	Discontinued
0.713	Intermediate Similarity	NPD690	Clinical (unspecified phase)
0.713	Intermediate Similarity	NPD1932	Approved
0.7103	Intermediate Similarity	NPD1238	Approved
0.71	Intermediate Similarity	NPD9257	Approved
0.71	Intermediate Similarity	NPD9259	Approved
0.708	Intermediate Similarity	NPD4141	Clinical (unspecified phase)
0.7054	Intermediate Similarity	NPD2182	Approved
0.7054	Intermediate Similarity	NPD2329	Discontinued
0.7043	Intermediate Similarity	NPD6010	Discontinued
0.703	Intermediate Similarity	NPD1087	Approved
0.7019	Intermediate Similarity	NPD7631	Approved
0.7019	Intermediate Similarity	NPD1088	Approved
0.7009	Intermediate Similarity	NPD9495	Approved
0.7	Intermediate Similarity	NPD1237	Approved
0.7	Intermediate Similarity	NPD164	Approved
0.6991	Remote Similarity	NPD1317	Discontinued
0.6984	Remote Similarity	NPD3268	Approved
0.6983	Remote Similarity	NPD2629	Approved
0.6981	Remote Similarity	NPD1989	Approved
0.6957	Remote Similarity	NPD6858	Approved
0.6957	Remote Similarity	NPD7094	Approved
0.6944	Remote Similarity	NPD7798	Approved
0.693	Remote Similarity	NPD2181	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD7609	Phase 3
0.6907	Remote Similarity	NPD9490	Approved
0.6891	Remote Similarity	NPD9545	Approved
0.6887	Remote Similarity	NPD6048	Clinical (unspecified phase)
0.6887	Remote Similarity	NPD6049	Phase 2
0.6885	Remote Similarity	NPD6637	Approved
0.6875	Remote Similarity	NPD3134	Approved
0.6875	Remote Similarity	NPD6685	Approved
0.6864	Remote Similarity	NPD9493	Approved
0.6863	Remote Similarity	NPD650	Approved
0.6838	Remote Similarity	NPD5951	Approved
0.6822	Remote Similarity	NPD5206	Clinical (unspecified phase)
0.6814	Remote Similarity	NPD9265	Clinical (unspecified phase)
0.681	Remote Similarity	NPD5277	Phase 2
0.68	Remote Similarity	NPD6007	Clinical (unspecified phase)
0.6768	Remote Similarity	NPD942	Approved
0.6762	Remote Similarity	NPD1239	Approved
0.6759	Remote Similarity	NPD1565	Approved
0.6759	Remote Similarity	NPD1566	Phase 3
0.6759	Remote Similarity	NPD1564	Approved
0.6759	Remote Similarity	NPD3495	Discontinued
0.6757	Remote Similarity	NPD5765	Approved
0.6731	Remote Similarity	NPD689	Discontinued
0.6724	Remote Similarity	NPD1609	Clinical (unspecified phase)
0.672	Remote Similarity	NPD3266	Approved
0.672	Remote Similarity	NPD3267	Approved
0.6667	Remote Similarity	NPD6287	Discontinued
0.6667	Remote Similarity	NPD9267	Approved
0.6667	Remote Similarity	NPD9264	Approved
0.6667	Remote Similarity	NPD1507	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD9263	Approved
0.6667	Remote Similarity	NPD1358	Approved
0.6639	Remote Similarity	NPD5305	Approved
0.6639	Remote Similarity	NPD5306	Approved
0.6639	Remote Similarity	NPD7163	Clinical (unspecified phase)
0.6636	Remote Similarity	NPD1066	Discontinued
0.6636	Remote Similarity	NPD1563	Approved
0.6615	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.6613	Remote Similarity	NPD4878	Approved
0.661	Remote Similarity	NPD1241	Discontinued
0.6609	Remote Similarity	NPD9266	Approved
0.6609	Remote Similarity	NPD74	Approved
0.6593	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6587	Remote Similarity	NPD2797	Approved
0.6574	Remote Similarity	NPD688	Clinical (unspecified phase)
0.6574	Remote Similarity	NPD9260	Approved
0.6532	Remote Similarity	NPD4807	Approved
0.6532	Remote Similarity	NPD4806	Approved
0.6512	Remote Similarity	NPD5952	Clinical (unspecified phase)
0.6508	Remote Similarity	NPD3225	Approved
0.6504	Remote Similarity	NPD3412	Clinical (unspecified phase)
0.6486	Remote Similarity	NPD3097	Clinical (unspecified phase)
0.648	Remote Similarity	NPD9717	Approved
0.6471	Remote Similarity	NPD2650	Approved
0.6471	Remote Similarity	NPD2652	Approved
0.646	Remote Similarity	NPD9261	Approved
0.6452	Remote Similarity	NPD4135	Approved
0.6452	Remote Similarity	NPD4106	Approved
0.6452	Remote Similarity	NPD4136	Approved
0.6452	Remote Similarity	NPD3847	Discontinued
0.6441	Remote Similarity	NPD6912	Phase 3
0.6441	Remote Similarity	NPD9508	Approved
0.6429	Remote Similarity	NPD4379	Clinical (unspecified phase)
0.6429	Remote Similarity	NPD3135	Clinical (unspecified phase)
0.6423	Remote Similarity	NPD4105	Approved
0.6423	Remote Similarity	NPD8166	Discontinued
0.6423	Remote Similarity	NPD4102	Approved
0.6423	Remote Similarity	NPD4196	Clinical (unspecified phase)
0.6422	Remote Similarity	NPD2933	Approved
0.6422	Remote Similarity	NPD2934	Approved
0.6417	Remote Similarity	NPD1246	Approved
0.6417	Remote Similarity	NPD9281	Approved
0.6406	Remote Similarity	NPD6085	Phase 2
0.6406	Remote Similarity	NPD5740	Clinical (unspecified phase)
0.6406	Remote Similarity	NPD2798	Approved
0.6396	Remote Similarity	NPD253	Approved
0.6393	Remote Similarity	NPD2347	Approved
0.6393	Remote Similarity	NPD5536	Phase 2
0.6389	Remote Similarity	NPD1508	Approved
0.6385	Remote Similarity	NPD7008	Discontinued
0.6381	Remote Similarity	NPD506	Clinical (unspecified phase)
0.6371	Remote Similarity	NPD1104	Approved
0.6371	Remote Similarity	NPD2345	Approved
0.6371	Remote Similarity	NPD2932	Approved
0.6364	Remote Similarity	NPD9294	Approved
0.6364	Remote Similarity	NPD2859	Approved
0.6364	Remote Similarity	NPD2860	Approved
0.6364	Remote Similarity	NPD4198	Discontinued
0.6356	Remote Similarity	NPD3642	Approved
0.6356	Remote Similarity	NPD3643	Approved
0.6356	Remote Similarity	NPD3644	Approved
0.6349	Remote Similarity	NPD3972	Approved
0.6341	Remote Similarity	NPD1894	Discontinued
0.6341	Remote Similarity	NPD7009	Phase 2
0.6339	Remote Similarity	NPD3020	Approved
0.6328	Remote Similarity	NPD1203	Approved
0.632	Remote Similarity	NPD3496	Discontinued
0.632	Remote Similarity	NPD4879	Approved
0.632	Remote Similarity	NPD7457	Clinical (unspecified phase)
0.6311	Remote Similarity	NPD405	Clinical (unspecified phase)
0.6311	Remote Similarity	NPD694	Clinical (unspecified phase)
0.6308	Remote Similarity	NPD6832	Phase 2
0.6306	Remote Similarity	NPD9566	Approved
0.6303	Remote Similarity	NPD969	Suspended
0.6299	Remote Similarity	NPD5158	Clinical (unspecified phase)
0.6299	Remote Similarity	NPD5157	Phase 1
0.6299	Remote Similarity	NPD5159	Phase 2
0.6296	Remote Similarity	NPD2799	Discontinued
0.629	Remote Similarity	NPD5981	Approved
0.629	Remote Similarity	NPD5585	Approved
0.6288	Remote Similarity	NPD7961	Discontinued
0.6279	Remote Similarity	NPD5647	Approved
0.6271	Remote Similarity	NPD5235	Approved
0.6271	Remote Similarity	NPD5237	Approved
0.6271	Remote Similarity	NPD5240	Approved
0.6271	Remote Similarity	NPD5236	Approved
0.6271	Remote Similarity	NPD5239	Approved
0.626	Remote Similarity	NPD7610	Discontinued
0.626	Remote Similarity	NPD1758	Phase 1
0.625	Remote Similarity	NPD2607	Approved
0.625	Remote Similarity	NPD2198	Approved
0.625	Remote Similarity	NPD2199	Approved
0.625	Remote Similarity	NPD2935	Discontinued
0.624	Remote Similarity	NPD4626	Approved
0.624	Remote Similarity	NPD1778	Approved
0.624	Remote Similarity	NPD3019	Approved
0.624	Remote Similarity	NPD1362	Clinical (unspecified phase)
0.6231	Remote Similarity	NPD5736	Approved
0.623	Remote Similarity	NPD3317	Approved
0.623	Remote Similarity	NPD255	Approved
0.623	Remote Similarity	NPD256	Approved
0.6228	Remote Similarity	NPD2171	Approved
0.6228	Remote Similarity	NPD2193	Phase 2
0.6228	Remote Similarity	NPD2648	Phase 3
0.622	Remote Similarity	NPD1608	Approved
0.6218	Remote Similarity	NPD2201	Approved
0.6216	Remote Similarity	NPD1843	Approved
0.6214	Remote Similarity	NPD7236	Approved
0.6212	Remote Similarity	NPD3764	Approved
0.6212	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6212	Remote Similarity	NPD2313	Discontinued
0.621	Remote Similarity	NPD1759	Phase 1
0.621	Remote Similarity	NPD4479	Discontinued
0.6207	Remote Similarity	NPD9697	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