NPASS Compound

Structure

NPC469847 OpenBabel07101719252D 44 49 0 0 1 0 0 0 0 0999 V2000 2.5981 -4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3612 1.1950 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6320 4.2052 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3198 0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5120 1.8685 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 0.1142 2.1594 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 -0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1965 -1.1303 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 -5.0625 -0.6303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0739 -1.4781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8943 2.5438 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8601 0.4523 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2709 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -3.0000 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 4.3163 2.1940 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6680 3.9391 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4533 -0.4612 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0685 -1.5827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 1.0000 0.0000 C 0 0 1 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 2.5860 2.1163 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.1288 2.2695 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.4752 -0.6691 0.0000 C 0 0 2 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 1.7321 1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8660 -0.5000 0.0000 C 0 0 2 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 1 0 0 0 0 0 0 0 0 0 2.6831 1.3090 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 5.1591 2.7324 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0443 4.6409 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5685 -2.4487 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.8546 0.3478 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.6831 -0.3090 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4287 2.6547 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.4165 2.9713 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 1 9 1 0 0 0 0 2 18 1 0 0 0 0 3 19 1 0 0 0 0 4 20 1 0 0 0 0 9 18 1 0 0 0 0 10 12 1 0 0 0 0 10 23 1 0 0 0 0 11 13 2 0 0 0 0 11 21 1 0 0 0 0 12 32 1 0 0 0 0 13 40 1 0 0 0 0 14 22 1 0 0 0 0 14 24 2 0 0 0 0 15 25 1 0 0 0 0 15 26 1 0 0 0 0 16 21 2 0 0 0 0 16 40 1 0 0 0 0 17 33 1 0 0 0 0 17 41 1 0 0 0 0 18 31 1 0 0 0 0 19 36 2 0 0 0 0 19 42 1 0 0 0 0 20 37 2 0 0 0 0 20 43 1 0 0 0 0 21 27 1 0 0 0 0 22 27 1 0 0 0 0 22 38 2 0 0 0 0 23 34 1 6 0 0 0 23 35 1 0 0 0 0 24 32 1 0 0 0 0 24 34 1 0 0 0 0 25 33 1 1 0 0 0 25 42 1 0 0 0 0 26 35 1 1 0 0 0 26 43 1 0 0 0 0 27 32 1 1 0 0 0 28 29 1 0 0 0 0 28 30 1 0 0 0 0 28 41 1 1 0 0 0 29 33 1 6 0 0 0 29 35 1 0 0 0 0 30 34 1 1 0 0 0 30 44 1 0 0 0 0 31 39 2 0 0 0 0 31 44 1 0 0 0 0 32 5 1 1 0 0 0 33 6 1 6 0 0 0 34 7 1 6 0 0 0 35 8 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	610.31
Volume:	623.234
LogP:	3.837
LogD:	3.068
LogS:	-5.08
# Rotatable Bonds:	9
TPSA:	118.34
# H-Bond Aceptor:	9
# H-Bond Donor:	0
# Rings:	6
# Heavy Atoms:	9

MedChem Properties

QED Drug-Likeness Score:	0.301
Synthetic Accessibility Score:	5.608
Fsp3:	0.714
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.204
MDCK Permeability:	4.2486790334805846e-05
Pgp-inhibitor:	1.0
Pgp-substrate:	0.003
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.948
30% Bioavailability (F30%):	0.905

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.371
Plasma Protein Binding (PPB):	86.48303985595703%
Volume Distribution (VD):	2.429
Pgp-substrate:	11.841465950012207%

ADMET: Metabolism

CYP1A2-inhibitor:	0.014
CYP1A2-substrate:	0.076
CYP2C19-inhibitor:	0.079
CYP2C19-substrate:	0.597
CYP2C9-inhibitor:	0.209
CYP2C9-substrate:	0.016
CYP2D6-inhibitor:	0.013
CYP2D6-substrate:	0.04
CYP3A4-inhibitor:	0.816
CYP3A4-substrate:	0.712

ADMET: Excretion

Clearance (CL):	4.727
Half-life (T1/2):	0.306

ADMET: Toxicity

hERG Blockers:	0.345
Human Hepatotoxicity (H-HT):	0.77
Drug-inuced Liver Injury (DILI):	0.556
AMES Toxicity:	0.006
Rat Oral Acute Toxicity:	0.842
Maximum Recommended Daily Dose:	0.941
Skin Sensitization:	0.156
Carcinogencity:	0.023
Eye Corrosion:	0.003
Eye Irritation:	0.012
Respiratory Toxicity:	0.975

Download Data

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

Natural Product: NPC469847

Natural Product ID:	NPC469847
*Common Name:**	Cipadesin L
IUPAC Name:	n.a.
Synonyms:	Cipadesin L
Standard InCHIKey:	GDQFZORSNBPGFF-QORDLJGISA-N
Standard InCHI:	InChI=1S/C35H46O9/c1-9-18(2)31(39)44-30-28-29-33(6,17-41-28)25(42-19(3)36)15-26(43-20(4)37)35(29,8)23-10-12-32(5)24(34(23,30)7)14-22(38)27(32)21-11-13-40-16-21/h11,13-14,16,18,23,25-30H,9-10,12,15,17H2,1-8H3/t18?,23-,25+,26-,27+,28+,29-,30+,32+,33+,34+,35-/m0/s1
SMILES:	CCC(C(=O)O[C@@H]1[C@@H]2OC[C@]3([C@H]2[C@]([C@@H]2[C@]1(C)C1=CC(=O)[C@H]([C@@]1(CC2)C)c1ccoc1)(C)[C@H](C[C@H]3OC(=O)C)OC(=O)C)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1215109
PubChem CID:	46918557
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001553] Triterpenoids [CHEMONTID:0002380] Limonoids

*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
NPO14263	Cipadessa baccifera	Species	Meliaceae	Eukaryota	leaves	n.a.	n.a.	PMID[20666364]
NPO14263	Cipadessa baccifera	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[32468815]
NPO14263	Cipadessa baccifera	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO14263	Cipadessa baccifera	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO14263	Cipadessa baccifera	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO14263	Cipadessa baccifera	Species	Meliaceae	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	5

Activity Type	# Activity
Cell Line	5

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT116	Cell Line	HL-60	Homo sapiens	IC50	>	40000.0	nM	PMID[518009]
NPT659	Cell Line	SMMC-7721	Homo sapiens	IC50	>	40000.0	nM	PMID[518009]
NPT81	Cell Line	A549	Homo sapiens	IC50	>	40000.0	nM	PMID[518009]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	>	40000.0	nM	PMID[518009]
NPT660	Cell Line	SW480	Homo sapiens	IC50	>	40000.0	nM	PMID[518009]

☑ 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 NPC469847 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	404
0.1-0.2	1447
0.2-0.3	3190
0.3-0.4	5774
0.4-0.5	10944
0.5-0.6	10494
0.6-0.7	9038
0.7-0.8	977
0.8-0.85	299
0.85-0.9	117
0.9-0.95	12
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.929	High Similarity	NPC470792
0.9272	High Similarity	NPC116717
0.9267	High Similarity	NPC471001
0.9211	High Similarity	NPC322546
0.9211	High Similarity	NPC308205
0.9211	High Similarity	NPC182427
0.9211	High Similarity	NPC472672
0.9211	High Similarity	NPC29695
0.9187	High Similarity	NPC469848
0.915	High Similarity	NPC34421
0.915	High Similarity	NPC98206
0.915	High Similarity	NPC302054
0.915	High Similarity	NPC237259
0.915	High Similarity	NPC253201
0.9067	High Similarity	NPC470999
0.9067	High Similarity	NPC471292
0.9038	High Similarity	NPC475226
0.902	High Similarity	NPC291150
0.8987	High Similarity	NPC471168
0.8974	High Similarity	NPC167142
0.8974	High Similarity	NPC470118
0.8974	High Similarity	NPC475066
0.8974	High Similarity	NPC214495
0.8974	High Similarity	NPC197137
0.8974	High Similarity	NPC470119
0.8968	High Similarity	NPC296807
0.8968	High Similarity	NPC92979
0.8968	High Similarity	NPC155939
0.8968	High Similarity	NPC141538
0.8961	High Similarity	NPC471002
0.8954	High Similarity	NPC5180
0.8933	High Similarity	NPC199044
0.8933	High Similarity	NPC238843
0.8931	High Similarity	NPC62692
0.8931	High Similarity	NPC126984
0.8931	High Similarity	NPC61967
0.8931	High Similarity	NPC27541
0.8924	High Similarity	NPC471166
0.8924	High Similarity	NPC471167
0.8924	High Similarity	NPC471003
0.8917	High Similarity	NPC472671
0.8896	High Similarity	NPC471000
0.8874	High Similarity	NPC34056
0.8868	High Similarity	NPC476197
0.8868	High Similarity	NPC285567
0.8861	High Similarity	NPC191828
0.8831	High Similarity	NPC156189
0.8824	High Similarity	NPC471007
0.8805	High Similarity	NPC68848
0.8774	High Similarity	NPC272590
0.8774	High Similarity	NPC18135
0.8773	High Similarity	NPC475237
0.8773	High Similarity	NPC285227
0.8773	High Similarity	NPC475641
0.8766	High Similarity	NPC470791
0.8766	High Similarity	NPC470790
0.8758	High Similarity	NPC216755
0.875	High Similarity	NPC469846
0.875	High Similarity	NPC14499
0.875	High Similarity	NPC283209
0.875	High Similarity	NPC476035
0.875	High Similarity	NPC475039
0.875	High Similarity	NPC472669
0.8734	High Similarity	NPC472283
0.8726	High Similarity	NPC476262
0.8718	High Similarity	NPC476201
0.8718	High Similarity	NPC470996
0.8718	High Similarity	NPC33938
0.8712	High Similarity	NPC118086
0.8712	High Similarity	NPC88593
0.871	High Similarity	NPC196846
0.871	High Similarity	NPC159927
0.871	High Similarity	NPC470997
0.871	High Similarity	NPC469335
0.8704	High Similarity	NPC310572
0.8688	High Similarity	NPC470939
0.8688	High Similarity	NPC472668
0.8688	High Similarity	NPC472771
0.8671	High Similarity	NPC175964
0.8671	High Similarity	NPC41880
0.8671	High Similarity	NPC471169
0.8671	High Similarity	NPC104736
0.8667	High Similarity	NPC56197
0.865	High Similarity	NPC160651
0.8645	High Similarity	NPC234494
0.8645	High Similarity	NPC472654
0.8642	High Similarity	NPC472141
0.8642	High Similarity	NPC121995
0.8642	High Similarity	NPC472670
0.8642	High Similarity	NPC307781
0.8639	High Similarity	NPC105395
0.8636	High Similarity	NPC255414
0.8636	High Similarity	NPC471174
0.8636	High Similarity	NPC71821
0.8634	High Similarity	NPC663
0.8634	High Similarity	NPC224394
0.8634	High Similarity	NPC472773
0.8616	High Similarity	NPC88007
0.8616	High Similarity	NPC195954
0.8616	High Similarity	NPC304692
0.8608	High Similarity	NPC471175
0.8608	High Similarity	NPC25351
0.8608	High Similarity	NPC469850
0.8599	High Similarity	NPC268905
0.8598	High Similarity	NPC470995
0.859	High Similarity	NPC196864
0.859	High Similarity	NPC477404
0.8589	High Similarity	NPC270312
0.8589	High Similarity	NPC476224
0.858	High Similarity	NPC469849
0.858	High Similarity	NPC276735
0.8571	High Similarity	NPC197596
0.8571	High Similarity	NPC329938
0.8553	High Similarity	NPC204663
0.8537	High Similarity	NPC327922
0.8537	High Similarity	NPC472673
0.8529	High Similarity	NPC242068
0.8529	High Similarity	NPC247563
0.8528	High Similarity	NPC470875
0.8526	High Similarity	NPC69647
0.8526	High Similarity	NPC125182
0.8519	High Similarity	NPC472139
0.8519	High Similarity	NPC469338
0.8519	High Similarity	NPC292389
0.8516	High Similarity	NPC302987
0.8516	High Similarity	NPC221809
0.8509	High Similarity	NPC470789
0.8509	High Similarity	NPC305016
0.8509	High Similarity	NPC287559
0.8506	High Similarity	NPC185456
0.85	High Similarity	NPC472777
0.85	High Similarity	NPC472776
0.85	High Similarity	NPC195131
0.85	High Similarity	NPC299038
0.85	High Similarity	NPC472778
0.85	High Similarity	NPC194499
0.85	High Similarity	NPC472772
0.8491	Intermediate Similarity	NPC264943
0.8491	Intermediate Similarity	NPC469336
0.8487	Intermediate Similarity	NPC20500
0.8481	Intermediate Similarity	NPC246164
0.8476	Intermediate Similarity	NPC476861
0.8476	Intermediate Similarity	NPC173516
0.8476	Intermediate Similarity	NPC472775
0.8476	Intermediate Similarity	NPC472282
0.8476	Intermediate Similarity	NPC476850
0.8476	Intermediate Similarity	NPC472774
0.8476	Intermediate Similarity	NPC472764
0.8471	Intermediate Similarity	NPC476122
0.8466	Intermediate Similarity	NPC276551
0.8466	Intermediate Similarity	NPC123088
0.8466	Intermediate Similarity	NPC56358
0.8466	Intermediate Similarity	NPC470940
0.8457	Intermediate Similarity	NPC18986
0.8457	Intermediate Similarity	NPC82851
0.8457	Intermediate Similarity	NPC69028
0.8457	Intermediate Similarity	NPC188649
0.8452	Intermediate Similarity	NPC478177
0.8447	Intermediate Similarity	NPC475967
0.8447	Intermediate Similarity	NPC237155
0.8447	Intermediate Similarity	NPC474932
0.8443	Intermediate Similarity	NPC94763
0.8443	Intermediate Similarity	NPC471437
0.8442	Intermediate Similarity	NPC251865
0.8438	Intermediate Similarity	NPC107646
0.8434	Intermediate Similarity	NPC294512
0.8428	Intermediate Similarity	NPC178932
0.8424	Intermediate Similarity	NPC472765
0.8424	Intermediate Similarity	NPC271235
0.8424	Intermediate Similarity	NPC471397
0.8424	Intermediate Similarity	NPC472766
0.8408	Intermediate Similarity	NPC470998
0.8408	Intermediate Similarity	NPC195325
0.8405	Intermediate Similarity	NPC477405
0.8405	Intermediate Similarity	NPC88841
0.8405	Intermediate Similarity	NPC419
0.8405	Intermediate Similarity	NPC165218
0.8405	Intermediate Similarity	NPC288602
0.8402	Intermediate Similarity	NPC11062
0.8395	Intermediate Similarity	NPC475381
0.8395	Intermediate Similarity	NPC25255
0.8395	Intermediate Similarity	NPC472653
0.8385	Intermediate Similarity	NPC1408
0.8385	Intermediate Similarity	NPC246841
0.8385	Intermediate Similarity	NPC286722
0.8377	Intermediate Similarity	NPC80635
0.8377	Intermediate Similarity	NPC223415
0.8377	Intermediate Similarity	NPC267632
0.8365	Intermediate Similarity	NPC84063
0.8365	Intermediate Similarity	NPC75906
0.8365	Intermediate Similarity	NPC294511
0.8365	Intermediate Similarity	NPC121615
0.8365	Intermediate Similarity	NPC469503
0.8354	Intermediate Similarity	NPC476856
0.8354	Intermediate Similarity	NPC476858
0.8354	Intermediate Similarity	NPC476857
0.8354	Intermediate Similarity	NPC212257
0.8344	Intermediate Similarity	NPC193798
0.8344	Intermediate Similarity	NPC5741
0.8344	Intermediate Similarity	NPC310043

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 NPC469847 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	332
0.1-0.2	951
0.2-0.3	2169
0.3-0.4	2729
0.4-0.5	1910
0.5-0.6	813
0.6-0.7	234
0.7-0.8	10
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
0.8148	Intermediate Similarity	NPD5760	Phase 2
0.8148	Intermediate Similarity	NPD5761	Phase 2
0.8046	Intermediate Similarity	NPD8434	Phase 2
0.7952	Intermediate Similarity	NPD5537	Clinical (unspecified phase)
0.7557	Intermediate Similarity	NPD6765	Approved
0.7557	Intermediate Similarity	NPD6764	Approved
0.7389	Intermediate Similarity	NPD6785	Approved
0.7389	Intermediate Similarity	NPD6784	Approved
0.7341	Intermediate Similarity	NPD8127	Discontinued
0.7293	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.716	Intermediate Similarity	NPD3226	Approved
0.7117	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7093	Intermediate Similarity	NPD7819	Suspended
0.7091	Intermediate Similarity	NPD4628	Phase 3
0.7086	Intermediate Similarity	NPD5494	Approved
0.7041	Intermediate Similarity	NPD920	Approved
0.7039	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.703	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7012	Intermediate Similarity	NPD1471	Phase 3
0.7011	Intermediate Similarity	NPD4965	Approved
0.7011	Intermediate Similarity	NPD4967	Phase 2
0.7011	Intermediate Similarity	NPD4966	Approved
0.7	Intermediate Similarity	NPD8032	Phase 2
0.6983	Remote Similarity	NPD7473	Discontinued
0.6982	Remote Similarity	NPD6273	Approved
0.6978	Remote Similarity	NPD6559	Discontinued
0.6954	Remote Similarity	NPD8443	Clinical (unspecified phase)
0.6949	Remote Similarity	NPD1247	Approved
0.6941	Remote Similarity	NPD6980	Clinical (unspecified phase)
0.6932	Remote Similarity	NPD6234	Discontinued
0.6932	Remote Similarity	NPD919	Approved
0.6923	Remote Similarity	NPD642	Clinical (unspecified phase)
0.6919	Remote Similarity	NPD6599	Discontinued
0.6915	Remote Similarity	NPD8404	Phase 2
0.6914	Remote Similarity	NPD4868	Clinical (unspecified phase)
0.6906	Remote Similarity	NPD5844	Phase 1
0.6897	Remote Similarity	NPD7096	Clinical (unspecified phase)
0.6879	Remote Similarity	NPD7411	Suspended
0.6875	Remote Similarity	NPD7075	Discontinued
0.6854	Remote Similarity	NPD7199	Phase 2
0.6839	Remote Similarity	NPD37	Approved
0.6816	Remote Similarity	NPD6232	Discontinued
0.6811	Remote Similarity	NPD8312	Approved
0.6811	Remote Similarity	NPD8313	Approved
0.6805	Remote Similarity	NPD643	Clinical (unspecified phase)
0.6788	Remote Similarity	NPD3748	Approved
0.6778	Remote Similarity	NPD7184	Clinical (unspecified phase)
0.6778	Remote Similarity	NPD3926	Phase 2
0.6763	Remote Similarity	NPD7458	Discontinued
0.6761	Remote Similarity	NPD3817	Phase 2
0.6758	Remote Similarity	NPD7228	Approved
0.6758	Remote Similarity	NPD7799	Discontinued
0.6747	Remote Similarity	NPD2796	Approved
0.6743	Remote Similarity	NPD6801	Discontinued
0.674	Remote Similarity	NPD7852	Clinical (unspecified phase)
0.6737	Remote Similarity	NPD7879	Clinical (unspecified phase)
0.6725	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6706	Remote Similarity	NPD7236	Approved
0.6686	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6685	Remote Similarity	NPD3749	Approved
0.6667	Remote Similarity	NPD5402	Approved
0.6667	Remote Similarity	NPD3818	Discontinued
0.6667	Remote Similarity	NPD6799	Approved
0.665	Remote Similarity	NPD7497	Discontinued
0.6649	Remote Similarity	NPD7993	Clinical (unspecified phase)
0.6632	Remote Similarity	NPD8397	Clinical (unspecified phase)
0.663	Remote Similarity	NPD6808	Phase 2
0.6629	Remote Similarity	NPD7768	Phase 2
0.6627	Remote Similarity	NPD1243	Approved
0.6625	Remote Similarity	NPD3266	Approved
0.6625	Remote Similarity	NPD3267	Approved
0.6615	Remote Similarity	NPD8285	Discontinued
0.6613	Remote Similarity	NPD7240	Approved
0.6613	Remote Similarity	NPD7685	Pre-registration
0.661	Remote Similarity	NPD2393	Clinical (unspecified phase)
0.6609	Remote Similarity	NPD7239	Suspended
0.6607	Remote Similarity	NPD2346	Discontinued
0.6605	Remote Similarity	NPD6832	Phase 2
0.659	Remote Similarity	NPD7314	Clinical (unspecified phase)
0.6588	Remote Similarity	NPD3750	Approved
0.6587	Remote Similarity	NPD2799	Discontinued
0.6573	Remote Similarity	NPD5616	Clinical (unspecified phase)
0.6571	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.657	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6562	Remote Similarity	NPD1876	Approved
0.6554	Remote Similarity	NPD1934	Approved
0.6552	Remote Similarity	NPD5403	Approved
0.6548	Remote Similarity	NPD2438	Suspended
0.6538	Remote Similarity	NPD7229	Phase 3
0.6536	Remote Similarity	NPD3882	Suspended
0.6534	Remote Similarity	NPD4380	Phase 2
0.6532	Remote Similarity	NPD2532	Approved
0.6532	Remote Similarity	NPD2533	Approved
0.6532	Remote Similarity	NPD5401	Approved
0.6532	Remote Similarity	NPD2534	Approved
0.6527	Remote Similarity	NPD7097	Phase 1
0.6524	Remote Similarity	NPD3268	Approved
0.6517	Remote Similarity	NPD8455	Phase 2
0.6509	Remote Similarity	NPD6004	Phase 3
0.6509	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.6509	Remote Similarity	NPD6005	Phase 3
0.6509	Remote Similarity	NPD6002	Phase 3
0.6509	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.6509	Remote Similarity	NPD5762	Approved
0.6509	Remote Similarity	NPD5763	Approved
0.6506	Remote Similarity	NPD6355	Discontinued
0.65	Remote Similarity	NPD4381	Clinical (unspecified phase)
0.6497	Remote Similarity	NPD4107	Approved
0.6491	Remote Similarity	NPD4110	Phase 3
0.6491	Remote Similarity	NPD4109	Clinical (unspecified phase)
0.6491	Remote Similarity	NPD8166	Discontinued
0.6491	Remote Similarity	NPD7003	Approved
0.6484	Remote Similarity	NPD6959	Discontinued
0.6467	Remote Similarity	NPD6167	Clinical (unspecified phase)
0.6467	Remote Similarity	NPD6168	Clinical (unspecified phase)
0.6467	Remote Similarity	NPD6166	Phase 2
0.6456	Remote Similarity	NPD17	Approved
0.6452	Remote Similarity	NPD7804	Clinical (unspecified phase)
0.645	Remote Similarity	NPD6100	Approved
0.645	Remote Similarity	NPD1551	Phase 2
0.645	Remote Similarity	NPD6099	Approved
0.6446	Remote Similarity	NPD4140	Approved
0.6441	Remote Similarity	NPD7028	Phase 2
0.644	Remote Similarity	NPD8150	Discontinued
0.6438	Remote Similarity	NPD3972	Approved
0.6437	Remote Similarity	NPD4378	Clinical (unspecified phase)
0.6425	Remote Similarity	NPD2801	Approved
0.6425	Remote Similarity	NPD1465	Phase 2
0.6424	Remote Similarity	NPD3764	Approved
0.6424	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6424	Remote Similarity	NPD2313	Discontinued
0.6421	Remote Similarity	NPD8407	Phase 2
0.6417	Remote Similarity	NPD7074	Phase 3
0.6412	Remote Similarity	NPD2344	Approved
0.6404	Remote Similarity	NPD6385	Approved
0.6404	Remote Similarity	NPD6386	Approved
0.6398	Remote Similarity	NPD5327	Phase 3
0.6389	Remote Similarity	NPD5353	Approved
0.6382	Remote Similarity	NPD4482	Phase 3
0.6374	Remote Similarity	NPD1549	Phase 2
0.6364	Remote Similarity	NPD7054	Approved
0.6364	Remote Similarity	NPD5952	Clinical (unspecified phase)
0.6358	Remote Similarity	NPD3887	Approved
0.6352	Remote Similarity	NPD3412	Clinical (unspecified phase)
0.6349	Remote Similarity	NPD8368	Discontinued
0.6347	Remote Similarity	NPD2979	Phase 3
0.6347	Remote Similarity	NPD4307	Phase 2
0.6343	Remote Similarity	NPD7410	Clinical (unspecified phase)
0.6337	Remote Similarity	NPD2800	Approved
0.6335	Remote Similarity	NPD1608	Approved
0.633	Remote Similarity	NPD7472	Approved
0.6325	Remote Similarity	NPD6798	Discontinued
0.6324	Remote Similarity	NPD5242	Approved
0.6319	Remote Similarity	NPD1049	Clinical (unspecified phase)
0.6318	Remote Similarity	NPD7435	Discontinued
0.6318	Remote Similarity	NPD7680	Approved
0.6316	Remote Similarity	NPD4338	Clinical (unspecified phase)
0.6316	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6316	Remote Similarity	NPD7808	Phase 3
0.6316	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.631	Remote Similarity	NPD5735	Approved
0.631	Remote Similarity	NPD3751	Discontinued
0.631	Remote Similarity	NPD1899	Clinical (unspecified phase)
0.631	Remote Similarity	NPD1933	Approved
0.629	Remote Similarity	NPD7784	Clinical (unspecified phase)
0.629	Remote Similarity	NPD2403	Approved
0.6289	Remote Similarity	NPD5585	Approved
0.6287	Remote Similarity	NPD6663	Approved
0.6287	Remote Similarity	NPD6233	Phase 2
0.628	Remote Similarity	NPD6007	Clinical (unspecified phase)
0.6279	Remote Similarity	NPD970	Clinical (unspecified phase)
0.6273	Remote Similarity	NPD1547	Clinical (unspecified phase)
0.627	Remote Similarity	NPD7315	Approved
0.6265	Remote Similarity	NPD7095	Approved
0.6264	Remote Similarity	NPD7058	Phase 2
0.6264	Remote Similarity	NPD2309	Approved
0.6264	Remote Similarity	NPD7057	Phase 3
0.6264	Remote Similarity	NPD6190	Approved
0.6263	Remote Similarity	NPD7251	Discontinued
0.6257	Remote Similarity	NPD2935	Discontinued
0.6244	Remote Similarity	NPD8151	Discontinued
0.6238	Remote Similarity	NPD7697	Approved
0.6238	Remote Similarity	NPD7696	Phase 3
0.6238	Remote Similarity	NPD7698	Approved
0.6223	Remote Similarity	NPD7177	Discontinued
0.6222	Remote Similarity	NPD7615	Clinical (unspecified phase)
0.6222	Remote Similarity	NPD6873	Phase 2
0.622	Remote Similarity	NPD2797	Approved
0.622	Remote Similarity	NPD7047	Phase 3
0.6214	Remote Similarity	NPD7874	Approved
0.6214	Remote Similarity	NPD7875	Clinical (unspecified phase)
0.6213	Remote Similarity	NPD447	Suspended
0.6211	Remote Similarity	NPD6797	Phase 2
0.6211	Remote Similarity	NPD5953	Discontinued
0.6207	Remote Similarity	NPD7871	Phase 2
0.6207	Remote Similarity	NPD7870	Phase 2
0.6207	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.6205	Remote Similarity	NPD8361	Approved
0.6205	Remote Similarity	NPD8360	Approved
0.6205	Remote Similarity	NPD8435	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