NPASS Compound

Structure

NPC472664 OpenBabel07101719512D 25 30 0 0 1 0 0 0 0 0999 V2000 -0.7444 0.1564 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1370 -0.8063 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 1.0000 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 -4.8639 -0.1124 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9921 2.2601 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5403 -0.0174 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2525 -0.3295 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6666 1.3094 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.7204 0.9711 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.3063 -0.6677 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6831 1.3090 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.4327 0.6591 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.6831 -0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 0.0000 0.0000 C 0 0 2 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 -0.5000 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -2.1270 -1.6515 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.9921 -1.2601 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.3660 -1.3660 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.4285 0.7932 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.2709 0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 17 1 0 0 0 0 2 5 2 0 0 0 0 2 9 1 0 0 0 0 3 4 1 0 0 0 0 3 18 1 0 0 0 0 4 19 1 0 0 0 0 5 23 1 0 0 0 0 7 11 1 0 0 0 0 7 12 1 0 0 0 0 8 18 1 0 0 0 0 8 24 1 0 0 0 0 9 12 1 0 0 0 0 9 14 2 0 0 0 0 10 6 1 6 0 0 0 10 11 1 0 0 0 0 10 14 1 0 0 0 0 11 18 1 6 0 0 0 12 20 2 0 0 0 0 13 6 1 6 0 0 0 13 15 1 0 0 0 0 13 25 1 0 0 0 0 14 23 1 0 0 0 0 15 17 1 6 0 0 0 15 18 1 0 0 0 0 16 17 1 0 0 0 0 16 21 2 0 0 0 0 16 25 1 0 0 0 0 17 19 1 6 0 0 0 19 22 1 0 0 0 0 19 24 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	344.13
Volume:	328.037
LogP:	1.244
LogD:	1.435
LogS:	-3.857
# Rotatable Bonds:	0
TPSA:	85.97
# H-Bond Aceptor:	6
# H-Bond Donor:	1
# Rings:	7
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.725
Synthetic Accessibility Score:	6.384
Fsp3:	0.684
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:	-5.246
MDCK Permeability:	1.5742854884592816e-05
Pgp-inhibitor:	0.444
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.005
20% Bioavailability (F20%):	0.376
30% Bioavailability (F30%):	0.232

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.091
Plasma Protein Binding (PPB):	85.36798858642578%
Volume Distribution (VD):	1.265
Pgp-substrate:	14.902181625366211%

ADMET: Metabolism

CYP1A2-inhibitor:	0.029
CYP1A2-substrate:	0.775
CYP2C19-inhibitor:	0.336
CYP2C19-substrate:	0.805
CYP2C9-inhibitor:	0.349
CYP2C9-substrate:	0.058
CYP2D6-inhibitor:	0.009
CYP2D6-substrate:	0.226
CYP3A4-inhibitor:	0.769
CYP3A4-substrate:	0.607

ADMET: Excretion

Clearance (CL):	9.1
Half-life (T1/2):	0.383

ADMET: Toxicity

hERG Blockers:	0.025
Human Hepatotoxicity (H-HT):	0.457
Drug-inuced Liver Injury (DILI):	0.793
AMES Toxicity:	0.08
Rat Oral Acute Toxicity:	0.742
Maximum Recommended Daily Dose:	0.806
Skin Sensitization:	0.051
Carcinogencity:	0.56
Eye Corrosion:	0.003
Eye Irritation:	0.023
Respiratory Toxicity:	0.215

Download Data

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

Natural Product: NPC472664

Natural Product ID:	NPC472664
*Common Name:**	CBUZTSOSSFLWTE-IFZAQDRASA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	CBUZTSOSSFLWTE-IFZAQDRASA-N
Standard InCHI:	InChI=1S/C19H20O6/c1-17-15-13(25-16(17)21)6-10-11(7-12(20)9-2-5-23-14(9)10)18(15)3-4-19(17,22)24-8-18/h2,5,10-11,13,15,22H,3-4,6-8H2,1H3/t10-,11-,13-,15+,17+,18?,19?/m1/s1
SMILES:	O=C1C[C@@H]2[C@H](c3c1cco3)C[C@@H]1[C@@H]3C42CCC(OC4)([C@]3(C)C(=O)O1)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3581407
PubChem CID:	n.a.
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0001640] Naphthopyrans

*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
NPO33310	Icacina trichantha	Species	Icacinaceae	Eukaryota	Tuber	n.a.	n.a.	PMID[25782063]
NPO33310	Icacina trichantha	Species	Icacinaceae	Eukaryota	Tuber	n.a.	n.a.	PMID[26523419]
NPO33310	Icacina trichantha	Species	Icacinaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[27340832]

☑ 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	3

Activity Type	# Activity
Cell Line	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT400	Cell Line	MDA-MB-435	Homo sapiens	IC50	>	20000.0	nM	PMID[482894]
NPT82	Cell Line	MDA-MB-231	Homo sapiens	IC50	>	20000.0	nM	PMID[482894]
NPT377	Cell Line	OVCAR-3	Homo sapiens	IC50	>	20000.0	nM	PMID[482894]

☑ 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 NPC472664 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	372
0.1-0.2	1572
0.2-0.3	3028
0.3-0.4	6022
0.4-0.5	10881
0.5-0.6	9126
0.6-0.7	8185
0.7-0.8	3179
0.8-0.85	296
0.85-0.9	33
0.9-0.95	1
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9444	High Similarity	NPC472665
0.9295	High Similarity	NPC81405
0.9236	High Similarity	NPC140952
0.9125	High Similarity	NPC56358
0.9108	High Similarity	NPC104736
0.9062	High Similarity	NPC419
0.9051	High Similarity	NPC304692
0.9018	High Similarity	NPC472660
0.9012	High Similarity	NPC270312
0.8938	High Similarity	NPC287559
0.8922	High Similarity	NPC472661
0.8896	High Similarity	NPC233763
0.8875	High Similarity	NPC474611
0.8868	High Similarity	NPC41880
0.8861	High Similarity	NPC178932
0.8834	High Similarity	NPC121995
0.8827	High Similarity	NPC283209
0.8827	High Similarity	NPC285567
0.8805	High Similarity	NPC469336
0.879	High Similarity	NPC196864
0.879	High Similarity	NPC477404
0.8765	High Similarity	NPC18986
0.8742	High Similarity	NPC30222
0.8726	High Similarity	NPC211625
0.872	High Similarity	NPC475779
0.8718	High Similarity	NPC224418
0.8688	High Similarity	NPC75310
0.8688	High Similarity	NPC35000
0.8679	High Similarity	NPC75906
0.8671	High Similarity	NPC159927
0.8671	High Similarity	NPC469335
0.8671	High Similarity	NPC212257
0.8654	High Similarity	NPC62799
0.865	High Similarity	NPC188649
0.865	High Similarity	NPC68848
0.8625	High Similarity	NPC282445
0.8608	High Similarity	NPC195325
0.8598	High Similarity	NPC88841
0.8598	High Similarity	NPC288602
0.8598	High Similarity	NPC477405
0.8581	High Similarity	NPC267632
0.858	High Similarity	NPC472772
0.858	High Similarity	NPC249021
0.8562	High Similarity	NPC475777
0.8562	High Similarity	NPC469503
0.8554	High Similarity	NPC473766
0.8554	High Similarity	NPC473753
0.8537	High Similarity	NPC69028
0.8537	High Similarity	NPC207978
0.8528	High Similarity	NPC473368
0.8526	High Similarity	NPC251865
0.8526	High Similarity	NPC84479
0.8512	High Similarity	NPC294512
0.8509	High Similarity	NPC57998
0.8509	High Similarity	NPC114880
0.8503	High Similarity	NPC296558
0.8491	Intermediate Similarity	NPC472654
0.8485	Intermediate Similarity	NPC469338
0.8485	Intermediate Similarity	NPC224394
0.8485	Intermediate Similarity	NPC663
0.8485	Intermediate Similarity	NPC292389
0.8481	Intermediate Similarity	NPC10088
0.8481	Intermediate Similarity	NPC250228
0.8476	Intermediate Similarity	NPC305016
0.8476	Intermediate Similarity	NPC333139
0.8471	Intermediate Similarity	NPC56953
0.8471	Intermediate Similarity	NPC176413
0.8466	Intermediate Similarity	NPC194499
0.8466	Intermediate Similarity	NPC88007
0.8466	Intermediate Similarity	NPC195954
0.8466	Intermediate Similarity	NPC299038
0.8462	Intermediate Similarity	NPC205071
0.8457	Intermediate Similarity	NPC472786
0.8457	Intermediate Similarity	NPC214541
0.8457	Intermediate Similarity	NPC469850
0.8457	Intermediate Similarity	NPC44675
0.8457	Intermediate Similarity	NPC264943
0.8452	Intermediate Similarity	NPC82602
0.8447	Intermediate Similarity	NPC246164
0.8447	Intermediate Similarity	NPC121615
0.8447	Intermediate Similarity	NPC476939
0.8447	Intermediate Similarity	NPC476940
0.8447	Intermediate Similarity	NPC294511
0.8443	Intermediate Similarity	NPC476850
0.8443	Intermediate Similarity	NPC100333
0.8443	Intermediate Similarity	NPC476861
0.8438	Intermediate Similarity	NPC228842
0.8438	Intermediate Similarity	NPC476122
0.8434	Intermediate Similarity	NPC469849
0.8434	Intermediate Similarity	NPC276735
0.8434	Intermediate Similarity	NPC276551
0.8434	Intermediate Similarity	NPC123088
0.8434	Intermediate Similarity	NPC470940
0.8434	Intermediate Similarity	NPC470182
0.8428	Intermediate Similarity	NPC19747
0.8424	Intermediate Similarity	NPC263432
0.8424	Intermediate Similarity	NPC211777
0.8424	Intermediate Similarity	NPC82851
0.8424	Intermediate Similarity	NPC472771
0.8418	Intermediate Similarity	NPC346
0.8415	Intermediate Similarity	NPC307383
0.8415	Intermediate Similarity	NPC475967
0.8408	Intermediate Similarity	NPC142113
0.8408	Intermediate Similarity	NPC476944
0.8402	Intermediate Similarity	NPC475237
0.8402	Intermediate Similarity	NPC475641
0.8397	Intermediate Similarity	NPC263337
0.8387	Intermediate Similarity	NPC148374
0.8385	Intermediate Similarity	NPC272590
0.8383	Intermediate Similarity	NPC93172
0.8383	Intermediate Similarity	NPC86800
0.8383	Intermediate Similarity	NPC470875
0.8383	Intermediate Similarity	NPC97574
0.8373	Intermediate Similarity	NPC198047
0.8373	Intermediate Similarity	NPC472773
0.8365	Intermediate Similarity	NPC221809
0.8365	Intermediate Similarity	NPC71821
0.8364	Intermediate Similarity	NPC25255
0.8364	Intermediate Similarity	NPC8389
0.8364	Intermediate Similarity	NPC472299
0.8363	Intermediate Similarity	NPC167340
0.8354	Intermediate Similarity	NPC7059
0.8354	Intermediate Similarity	NPC261597
0.8354	Intermediate Similarity	NPC472283
0.8344	Intermediate Similarity	NPC179170
0.8344	Intermediate Similarity	NPC103134
0.8344	Intermediate Similarity	NPC92979
0.8344	Intermediate Similarity	NPC25351
0.8343	Intermediate Similarity	NPC44602
0.8343	Intermediate Similarity	NPC472662
0.8343	Intermediate Similarity	NPC472663
0.8333	Intermediate Similarity	NPC476201
0.8333	Intermediate Similarity	NPC472282
0.8333	Intermediate Similarity	NPC173516
0.8323	Intermediate Similarity	NPC476936
0.8323	Intermediate Similarity	NPC202260
0.8323	Intermediate Similarity	NPC476856
0.8323	Intermediate Similarity	NPC476858
0.8323	Intermediate Similarity	NPC476860
0.8323	Intermediate Similarity	NPC476857
0.8313	Intermediate Similarity	NPC117986
0.8313	Intermediate Similarity	NPC200782
0.8313	Intermediate Similarity	NPC476942
0.8313	Intermediate Similarity	NPC329938
0.8313	Intermediate Similarity	NPC193798
0.8313	Intermediate Similarity	NPC476941
0.8313	Intermediate Similarity	NPC79571
0.8313	Intermediate Similarity	NPC5079
0.8312	Intermediate Similarity	NPC42400
0.8303	Intermediate Similarity	NPC262872
0.8303	Intermediate Similarity	NPC477403
0.8302	Intermediate Similarity	NPC262198
0.8302	Intermediate Similarity	NPC276676
0.8294	Intermediate Similarity	NPC169299
0.8294	Intermediate Similarity	NPC160818
0.8293	Intermediate Similarity	NPC60973
0.8284	Intermediate Similarity	NPC471397
0.8284	Intermediate Similarity	NPC160651
0.828	Intermediate Similarity	NPC121158
0.8274	Intermediate Similarity	NPC472141
0.8274	Intermediate Similarity	NPC23387
0.8272	Intermediate Similarity	NPC144010
0.8269	Intermediate Similarity	NPC18904
0.8266	Intermediate Similarity	NPC295914
0.8263	Intermediate Similarity	NPC234660
0.8263	Intermediate Similarity	NPC472139
0.8263	Intermediate Similarity	NPC51568
0.8258	Intermediate Similarity	NPC476943
0.8253	Intermediate Similarity	NPC477402
0.8253	Intermediate Similarity	NPC335761
0.8253	Intermediate Similarity	NPC191828
0.825	Intermediate Similarity	NPC476938
0.825	Intermediate Similarity	NPC476937
0.825	Intermediate Similarity	NPC216755
0.825	Intermediate Similarity	NPC471174
0.825	Intermediate Similarity	NPC470941
0.8242	Intermediate Similarity	NPC36655
0.8242	Intermediate Similarity	NPC221992
0.8242	Intermediate Similarity	NPC472778
0.8242	Intermediate Similarity	NPC472777
0.8242	Intermediate Similarity	NPC472776
0.8242	Intermediate Similarity	NPC167142
0.8242	Intermediate Similarity	NPC187149
0.8239	Intermediate Similarity	NPC41182
0.8235	Intermediate Similarity	NPC320789
0.8235	Intermediate Similarity	NPC302392
0.8232	Intermediate Similarity	NPC476262
0.8232	Intermediate Similarity	NPC472785
0.8232	Intermediate Similarity	NPC281258
0.8232	Intermediate Similarity	NPC88958
0.8228	Intermediate Similarity	NPC223415
0.8228	Intermediate Similarity	NPC64568
0.8225	Intermediate Similarity	NPC476853
0.8225	Intermediate Similarity	NPC472775
0.8225	Intermediate Similarity	NPC472774
0.8225	Intermediate Similarity	NPC472784
0.8221	Intermediate Similarity	NPC145830
0.8221	Intermediate Similarity	NPC268905
0.8217	Intermediate Similarity	NPC20500
0.8214	Intermediate Similarity	NPC261184

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 NPC472664 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	320
0.1-0.2	900
0.2-0.3	1832
0.3-0.4	2722
0.4-0.5	2157
0.5-0.6	895
0.6-0.7	270
0.7-0.8	51
0.8-0.85	3
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8476	Intermediate Similarity	NPD5537	Clinical (unspecified phase)
0.8125	Intermediate Similarity	NPD8434	Phase 2
0.8012	Intermediate Similarity	NPD5760	Phase 2
0.8012	Intermediate Similarity	NPD5761	Phase 2
0.7771	Intermediate Similarity	NPD3226	Approved
0.775	Intermediate Similarity	NPD1471	Phase 3
0.774	Intermediate Similarity	NPD6765	Approved
0.774	Intermediate Similarity	NPD6764	Approved
0.7692	Intermediate Similarity	NPD7819	Suspended
0.7679	Intermediate Similarity	NPD7411	Suspended
0.7651	Intermediate Similarity	NPD920	Approved
0.764	Intermediate Similarity	NPD6559	Discontinued
0.764	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7572	Intermediate Similarity	NPD5494	Approved
0.7569	Intermediate Similarity	NPD6784	Approved
0.7569	Intermediate Similarity	NPD6785	Approved
0.7558	Intermediate Similarity	NPD3749	Approved
0.7546	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7544	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7531	Intermediate Similarity	NPD2346	Discontinued
0.7514	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD4628	Phase 3
0.7485	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7459	Intermediate Similarity	NPD8312	Approved
0.7459	Intermediate Similarity	NPD8313	Approved
0.7429	Intermediate Similarity	NPD6959	Discontinued
0.7425	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7425	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7423	Intermediate Similarity	NPD2344	Approved
0.7412	Intermediate Similarity	NPD6599	Discontinued
0.7407	Intermediate Similarity	NPD2799	Discontinued
0.7401	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7381	Intermediate Similarity	NPD6273	Approved
0.7356	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7356	Intermediate Similarity	NPD7075	Discontinued
0.7333	Intermediate Similarity	NPD2800	Approved
0.7321	Intermediate Similarity	NPD2533	Approved
0.7321	Intermediate Similarity	NPD2532	Approved
0.7321	Intermediate Similarity	NPD2534	Approved
0.7305	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7288	Intermediate Similarity	NPD6808	Phase 2
0.7283	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7283	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD1549	Phase 2
0.7256	Intermediate Similarity	NPD2796	Approved
0.7251	Intermediate Similarity	NPD7458	Discontinued
0.725	Intermediate Similarity	NPD2313	Discontinued
0.7246	Intermediate Similarity	NPD2309	Approved
0.7225	Intermediate Similarity	NPD6801	Discontinued
0.7222	Intermediate Similarity	NPD3818	Discontinued
0.7219	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7212	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7212	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7209	Intermediate Similarity	NPD4380	Phase 2
0.7182	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7182	Intermediate Similarity	NPD5844	Phase 1
0.7167	Intermediate Similarity	NPD7473	Discontinued
0.7164	Intermediate Similarity	NPD8404	Phase 2
0.716	Intermediate Similarity	NPD6799	Approved
0.7152	Intermediate Similarity	NPD1551	Phase 2
0.7151	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD7074	Phase 3
0.7135	Intermediate Similarity	NPD1247	Approved
0.7126	Intermediate Similarity	NPD1243	Approved
0.7126	Intermediate Similarity	NPD1934	Approved
0.7119	Intermediate Similarity	NPD919	Approved
0.7107	Intermediate Similarity	NPD2798	Approved
0.7102	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7102	Intermediate Similarity	NPD4965	Approved
0.7102	Intermediate Similarity	NPD4966	Approved
0.7102	Intermediate Similarity	NPD7768	Phase 2
0.7102	Intermediate Similarity	NPD4967	Phase 2
0.7095	Intermediate Similarity	NPD6232	Discontinued
0.7088	Intermediate Similarity	NPD7054	Approved
0.7083	Intermediate Similarity	NPD3750	Approved
0.7083	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7066	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7049	Intermediate Similarity	NPD7472	Approved
0.7048	Intermediate Similarity	NPD2935	Discontinued
0.7045	Intermediate Similarity	NPD5402	Approved
0.7045	Intermediate Similarity	NPD3817	Phase 2
0.7039	Intermediate Similarity	NPD8127	Discontinued
0.7037	Intermediate Similarity	NPD3268	Approved
0.7033	Intermediate Similarity	NPD7799	Discontinued
0.7033	Intermediate Similarity	NPD7228	Approved
0.7027	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7022	Intermediate Similarity	NPD6234	Discontinued
0.7018	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7017	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7017	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7017	Intermediate Similarity	NPD6166	Phase 2
0.7011	Intermediate Similarity	NPD6797	Phase 2
0.7006	Intermediate Similarity	NPD3882	Suspended
0.7	Intermediate Similarity	NPD7236	Approved
0.6988	Remote Similarity	NPD3748	Approved
0.6988	Remote Similarity	NPD7033	Discontinued
0.6988	Remote Similarity	NPD1510	Phase 2
0.6984	Remote Similarity	NPD8397	Clinical (unspecified phase)
0.6982	Remote Similarity	NPD7003	Approved
0.6973	Remote Similarity	NPD7251	Discontinued
0.6962	Remote Similarity	NPD1608	Approved
0.6961	Remote Similarity	NPD3926	Phase 2
0.6959	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6946	Remote Similarity	NPD6099	Approved
0.6946	Remote Similarity	NPD6100	Approved
0.694	Remote Similarity	NPD3751	Discontinued
0.6936	Remote Similarity	NPD5403	Approved
0.6935	Remote Similarity	NPD7808	Phase 3
0.6933	Remote Similarity	NPD1699	Clinical (unspecified phase)
0.6932	Remote Similarity	NPD37	Approved
0.6928	Remote Similarity	NPD7097	Phase 1
0.6919	Remote Similarity	NPD5401	Approved
0.6914	Remote Similarity	NPD6832	Phase 2
0.6906	Remote Similarity	NPD5710	Approved
0.6906	Remote Similarity	NPD5711	Approved
0.6905	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.6905	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.6905	Remote Similarity	NPD6004	Phase 3
0.6905	Remote Similarity	NPD6005	Phase 3
0.6905	Remote Similarity	NPD6002	Phase 3
0.6904	Remote Similarity	NPD7435	Discontinued
0.6899	Remote Similarity	NPD1547	Clinical (unspecified phase)
0.6893	Remote Similarity	NPD2801	Approved
0.6893	Remote Similarity	NPD8455	Phase 2
0.6893	Remote Similarity	NPD1465	Phase 2
0.6882	Remote Similarity	NPD7240	Approved
0.6867	Remote Similarity	NPD1607	Approved
0.6855	Remote Similarity	NPD3972	Approved
0.6851	Remote Similarity	NPD7199	Phase 2
0.6848	Remote Similarity	NPD1240	Approved
0.6839	Remote Similarity	NPD6980	Clinical (unspecified phase)
0.6837	Remote Similarity	NPD6781	Approved
0.6837	Remote Similarity	NPD6778	Approved
0.6837	Remote Similarity	NPD6782	Approved
0.6837	Remote Similarity	NPD6777	Approved
0.6837	Remote Similarity	NPD6780	Approved
0.6837	Remote Similarity	NPD6776	Approved
0.6837	Remote Similarity	NPD6779	Approved
0.6836	Remote Similarity	NPD6280	Approved
0.6836	Remote Similarity	NPD6279	Approved
0.6832	Remote Similarity	NPD3266	Approved
0.6832	Remote Similarity	NPD3267	Approved
0.6829	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6829	Remote Similarity	NPD3764	Approved
0.6828	Remote Similarity	NPD7993	Clinical (unspecified phase)
0.6828	Remote Similarity	NPD5953	Discontinued
0.6818	Remote Similarity	NPD7696	Phase 3
0.6818	Remote Similarity	NPD7698	Approved
0.6818	Remote Similarity	NPD7697	Approved
0.6813	Remote Similarity	NPD3787	Discontinued
0.6813	Remote Similarity	NPD7229	Phase 3
0.6811	Remote Similarity	NPD7286	Phase 2
0.6807	Remote Similarity	NPD1899	Clinical (unspecified phase)
0.6807	Remote Similarity	NPD1933	Approved
0.68	Remote Similarity	NPD7239	Suspended
0.6794	Remote Similarity	NPD5619	Clinical (unspecified phase)
0.6791	Remote Similarity	NPD7685	Pre-registration
0.6789	Remote Similarity	NPD8150	Discontinued
0.6788	Remote Similarity	NPD8032	Phase 2
0.6786	Remote Similarity	NPD8285	Discontinued
0.678	Remote Similarity	NPD5890	Approved
0.678	Remote Similarity	NPD5889	Approved
0.6776	Remote Similarity	NPD7184	Clinical (unspecified phase)
0.6772	Remote Similarity	NPD17	Approved
0.6768	Remote Similarity	NPD5952	Clinical (unspecified phase)
0.6766	Remote Similarity	NPD6651	Approved
0.6763	Remote Similarity	NPD1511	Approved
0.676	Remote Similarity	NPD2296	Approved
0.6757	Remote Similarity	NPD7177	Discontinued
0.675	Remote Similarity	NPD9717	Approved
0.6747	Remote Similarity	NPD4140	Approved
0.6742	Remote Similarity	NPD6844	Discontinued
0.6733	Remote Similarity	NPD8151	Discontinued
0.6728	Remote Similarity	NPD2797	Approved
0.6728	Remote Similarity	NPD1203	Approved
0.6723	Remote Similarity	NPD7028	Phase 2
0.6719	Remote Similarity	NPD4287	Approved
0.6707	Remote Similarity	NPD6355	Discontinued
0.6707	Remote Similarity	NPD447	Suspended
0.67	Remote Similarity	NPD7874	Approved
0.67	Remote Similarity	NPD8320	Phase 1
0.67	Remote Similarity	NPD7870	Phase 2
0.67	Remote Similarity	NPD7875	Clinical (unspecified phase)
0.67	Remote Similarity	NPD7871	Phase 2
0.67	Remote Similarity	NPD8319	Approved
0.6687	Remote Similarity	NPD6007	Clinical (unspecified phase)
0.6686	Remote Similarity	NPD1512	Approved
0.6686	Remote Similarity	NPD4308	Phase 3
0.6686	Remote Similarity	NPD4110	Phase 3
0.6686	Remote Similarity	NPD4109	Clinical (unspecified phase)
0.6684	Remote Similarity	NPD8407	Phase 2
0.6683	Remote Similarity	NPD7701	Phase 2
0.6667	Remote Similarity	NPD7783	Phase 2
0.6667	Remote Similarity	NPD7782	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD4419	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD4107	Approved
0.6667	Remote Similarity	NPD5616	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD1778	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