NPASS Compound

Structure

NPC472764 OpenBabel07101719152D 43 47 0 0 1 0 0 0 0 0999 V2000 -0.9176 -0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7864 0.8612 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3668 -1.4739 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1348 -2.0101 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6348 -1.1441 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1349 -0.3508 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6158 -0.2045 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6524 -2.9792 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6245 -0.9000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.6245 -0.9000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0543 -2.4792 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4623 0.9781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1245 0.6389 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0824 -0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9204 1.3612 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3668 -0.4739 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3155 0.0511 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0543 -1.4792 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.9204 -2.9792 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2054 1.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6702 -1.6180 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.0543 -0.1388 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.0000 -1.6180 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6213 -1.3090 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.3644 0.3601 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.6348 -0.4739 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.4739 -0.4739 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.6348 -1.1441 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4739 -1.1441 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.6213 -0.3090 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.6702 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.9204 2.3612 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.2328 0.0261 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.9204 -3.9792 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.9975 2.6254 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.3827 -2.5419 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.4303 -1.8968 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.7864 -2.4792 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.9335 0.0511 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.0543 0.8612 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5008 0.0261 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.1565 1.3383 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 1 14 2 0 0 0 0 2 15 1 0 0 0 0 3 16 1 0 0 0 0 4 28 1 0 0 0 0 5 28 1 0 0 0 0 7 30 1 0 0 0 0 8 38 1 0 0 0 0 9 10 2 0 0 0 0 9 17 1 0 0 0 0 10 39 1 0 0 0 0 11 18 1 0 0 0 0 11 19 1 0 0 0 0 12 20 1 0 0 0 0 13 17 2 0 0 0 0 13 39 1 0 0 0 0 14 31 1 0 0 0 0 15 32 2 0 0 0 0 15 40 1 0 0 0 0 16 33 2 0 0 0 0 16 41 1 0 0 0 0 17 25 1 0 0 0 0 18 28 1 0 0 0 0 18 29 1 1 0 0 0 19 34 2 0 0 0 0 19 38 1 0 0 0 0 20 35 2 0 0 0 0 20 42 1 0 0 0 0 21 14 1 1 0 0 0 21 23 1 0 0 0 0 21 24 1 0 0 0 0 22 26 1 0 0 0 0 22 27 1 0 0 0 0 22 40 1 6 0 0 0 23 29 1 0 0 0 0 23 36 2 0 0 0 0 24 30 1 1 0 0 0 24 37 1 0 0 0 0 25 30 1 1 0 0 0 25 42 1 0 0 0 0 26 28 1 0 0 0 0 26 41 1 6 0 0 0 27 29 1 6 0 0 0 27 43 1 0 0 0 0 29 6 1 1 0 0 0 30 31 1 1 0 0 0 31 12 1 1 0 0 0 31 43 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	602.24
Volume:	586.341
LogP:	2.401
LogD:	2.143
LogS:	-4.351
# Rotatable Bonds:	8
TPSA:	164.87
# H-Bond Aceptor:	12
# H-Bond Donor:	1
# Rings:	5
# Heavy Atoms:	12

MedChem Properties

QED Drug-Likeness Score:	0.388
Synthetic Accessibility Score:	6.594
Fsp3:	0.645
Lipinski Rule-of-5:	Rejected
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:	-5.237
MDCK Permeability:	6.072648102417588e-05
Pgp-inhibitor:	1.0
Pgp-substrate:	0.725
Human Intestinal Absorption (HIA):	0.731
20% Bioavailability (F20%):	0.309
30% Bioavailability (F30%):	0.983

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.443
Plasma Protein Binding (PPB):	65.87889862060547%
Volume Distribution (VD):	0.771
Pgp-substrate:	32.60242462158203%

ADMET: Metabolism

CYP1A2-inhibitor:	0.004
CYP1A2-substrate:	0.053
CYP2C19-inhibitor:	0.021
CYP2C19-substrate:	0.257
CYP2C9-inhibitor:	0.153
CYP2C9-substrate:	0.023
CYP2D6-inhibitor:	0.119
CYP2D6-substrate:	0.087
CYP3A4-inhibitor:	0.446
CYP3A4-substrate:	0.65

ADMET: Excretion

Clearance (CL):	7.607
Half-life (T1/2):	0.11

ADMET: Toxicity

hERG Blockers:	0.004
Human Hepatotoxicity (H-HT):	0.602
Drug-inuced Liver Injury (DILI):	0.872
AMES Toxicity:	0.037
Rat Oral Acute Toxicity:	0.994
Maximum Recommended Daily Dose:	0.781
Skin Sensitization:	0.068
Carcinogencity:	0.094
Eye Corrosion:	0.003
Eye Irritation:	0.009
Respiratory Toxicity:	0.966

Download Data

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

Natural Product: NPC472764

Natural Product ID:	NPC472764
*Common Name:**	MFLYZNIXAUNUGD-PCMDOYLASA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	MFLYZNIXAUNUGD-PCMDOYLASA-N
Standard InCHI:	InChI=1S/C31H38O12/c1-14-21-23(36)29(6)18(11-19(34)38-8)28(4,5)26(41-16(3)33)22(40-15(2)32)27(29)43-31(14)12-20(35)42-25(17-9-10-39-13-17)30(31,7)24(21)37/h9-10,13,18,21-22,24-27,37H,1,11-12H2,2-8H3/t18-,21-,22-,24-,25-,26+,27-,29-,30-,31-/m0/s1
SMILES:	CC(=O)OC1C2C(C(C(C1OC(=O)C)(C)C)CC(=O)OC)(C(=O)C3C(C4(C(OC(=O)CC4(C3=C)O2)C5=COC=C5)C)O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3582093
PubChem CID:	n.a.
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000264] Organic acids and derivatives [CHEMONTID:0000265] Carboxylic acids and derivatives [CHEMONTID:0002966] Tetracarboxylic acids and derivatives

*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
NPO4584	Cipadessa cinerascens	Species	Meliaceae	Eukaryota	leaves	n.a.	n.a.	PMID[17655260]
NPO4584	Cipadessa cinerascens	Species	Meliaceae	Eukaryota	Leaves	n.a.	n.a.	PMID[19296669]
NPO4584	Cipadessa cinerascens	Species	Meliaceae	Eukaryota	leaves	Longlin County of Guangxi Province, China	2012-JUL	PMID[25970729]
NPO4584	Cipadessa cinerascens	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
EC50	1

Activity Type	# Activity
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT24	Organism	Human immunodeficiency virus 1	Human immunodeficiency virus 1	EC50	>	100000.0	nM	PMID[506304]

☑ 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 NPC472764 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	355
0.1-0.2	1428
0.2-0.3	3243
0.3-0.4	5702
0.4-0.5	10911
0.5-0.6	10219
0.6-0.7	9098
0.7-0.8	1320
0.8-0.85	311
0.85-0.9	97
0.9-0.95	5
0.95-1	8

Similarity Score	Similarity Level	Natural Product ID
0.9936	High Similarity	NPC472765
0.9936	High Similarity	NPC472766
0.9742	High Similarity	NPC472767
0.9557	High Similarity	NPC149945
0.9548	High Similarity	NPC195131
0.9497	High Similarity	NPC476224
0.9484	High Similarity	NPC204663
0.9367	High Similarity	NPC6326
0.9367	High Similarity	NPC472771
0.9308	High Similarity	NPC472773
0.9207	High Similarity	NPC471632
0.9202	High Similarity	NPC285227
0.9187	High Similarity	NPC165218
0.9177	High Similarity	NPC472772
0.9136	High Similarity	NPC472774
0.9136	High Similarity	NPC472775
0.9096	High Similarity	NPC478177
0.9091	High Similarity	NPC94763
0.9091	High Similarity	NPC236004
0.9091	High Similarity	NPC471437
0.9068	High Similarity	NPC472669
0.9057	High Similarity	NPC167142
0.9024	High Similarity	NPC472659
0.9006	High Similarity	NPC472668
0.9006	High Similarity	NPC471167
0.9006	High Similarity	NPC471166
0.8951	High Similarity	NPC471168
0.8931	High Similarity	NPC264943
0.8902	High Similarity	NPC476853
0.8896	High Similarity	NPC276551
0.8889	High Similarity	NPC5741
0.8882	High Similarity	NPC475226
0.8876	High Similarity	NPC470938
0.8862	High Similarity	NPC469576
0.8848	High Similarity	NPC327922
0.8848	High Similarity	NPC471397
0.8841	High Similarity	NPC470875
0.8841	High Similarity	NPC214600
0.8841	High Similarity	NPC478178
0.8834	High Similarity	NPC477405
0.8834	High Similarity	NPC292389
0.8834	High Similarity	NPC469338
0.8827	High Similarity	NPC470789
0.8827	High Similarity	NPC477402
0.882	High Similarity	NPC472776
0.882	High Similarity	NPC472777
0.882	High Similarity	NPC197137
0.882	High Similarity	NPC45101
0.882	High Similarity	NPC472778
0.882	High Similarity	NPC475066
0.8812	High Similarity	NPC469336
0.881	High Similarity	NPC469633
0.8797	High Similarity	NPC156189
0.8788	High Similarity	NPC476861
0.8788	High Similarity	NPC472651
0.8788	High Similarity	NPC476850
0.8788	High Similarity	NPC173516
0.878	High Similarity	NPC476857
0.878	High Similarity	NPC469849
0.878	High Similarity	NPC470940
0.878	High Similarity	NPC476856
0.878	High Similarity	NPC123088
0.878	High Similarity	NPC476858
0.8773	High Similarity	NPC82851
0.8773	High Similarity	NPC69028
0.8773	High Similarity	NPC200782
0.8765	High Similarity	NPC475967
0.8765	High Similarity	NPC477403
0.875	High Similarity	NPC178932
0.8743	High Similarity	NPC159232
0.8735	High Similarity	NPC472652
0.8735	High Similarity	NPC160651
0.8735	High Similarity	NPC472673
0.8734	High Similarity	NPC472654
0.8727	High Similarity	NPC23387
0.8721	High Similarity	NPC247563
0.8721	High Similarity	NPC242068
0.8721	High Similarity	NPC105395
0.872	High Similarity	NPC663
0.872	High Similarity	NPC224394
0.8712	High Similarity	NPC25255
0.8704	High Similarity	NPC299038
0.8704	High Similarity	NPC470118
0.8696	High Similarity	NPC92979
0.8696	High Similarity	NPC471175
0.869	High Similarity	NPC469848
0.8688	High Similarity	NPC469503
0.8688	High Similarity	NPC75906
0.8688	High Similarity	NPC476201
0.8675	High Similarity	NPC478179
0.8675	High Similarity	NPC472282
0.8667	High Similarity	NPC476860
0.8659	High Similarity	NPC329938
0.8659	High Similarity	NPC263432
0.8659	High Similarity	NPC193798
0.865	High Similarity	NPC237155
0.865	High Similarity	NPC472671
0.865	High Similarity	NPC472779
0.8642	High Similarity	NPC471169
0.8642	High Similarity	NPC175964
0.8634	High Similarity	NPC282445
0.8625	High Similarity	NPC116717
0.8625	High Similarity	NPC18135
0.8623	High Similarity	NPC271235
0.8616	High Similarity	NPC470791
0.8616	High Similarity	NPC69647
0.8616	High Similarity	NPC125182
0.8616	High Similarity	NPC470790
0.8614	High Similarity	NPC121995
0.8608	High Similarity	NPC470941
0.8608	High Similarity	NPC255414
0.8606	High Similarity	NPC134254
0.8606	High Similarity	NPC39986
0.8606	High Similarity	NPC476197
0.8606	High Similarity	NPC302369
0.8598	High Similarity	NPC472653
0.8589	High Similarity	NPC36655
0.8589	High Similarity	NPC470119
0.8589	High Similarity	NPC214495
0.8589	High Similarity	NPC249021
0.8589	High Similarity	NPC261597
0.858	High Similarity	NPC44675
0.858	High Similarity	NPC214541
0.858	High Similarity	NPC476262
0.8571	High Similarity	NPC470995
0.8571	High Similarity	NPC29695
0.8571	High Similarity	NPC472672
0.8571	High Similarity	NPC84063
0.8571	High Similarity	NPC182427
0.8562	High Similarity	NPC469335
0.8562	High Similarity	NPC196864
0.8562	High Similarity	NPC159927
0.8562	High Similarity	NPC477404
0.8554	High Similarity	NPC470182
0.8554	High Similarity	NPC259943
0.8554	High Similarity	NPC271657
0.8545	High Similarity	NPC470939
0.8545	High Similarity	NPC188649
0.8545	High Similarity	NPC197596
0.8545	High Similarity	NPC18986
0.8545	High Similarity	NPC5079
0.8545	High Similarity	NPC470792
0.8537	High Similarity	NPC474932
0.8528	High Similarity	NPC469485
0.8519	High Similarity	NPC253201
0.8519	High Similarity	NPC302054
0.8519	High Similarity	NPC57998
0.8503	High Similarity	NPC307781
0.8503	High Similarity	NPC472141
0.8503	High Similarity	NPC93172
0.8503	High Similarity	NPC472670
0.8503	High Similarity	NPC97574
0.85	High Similarity	NPC195325
0.85	High Similarity	NPC329180
0.8494	Intermediate Similarity	NPC51568
0.8494	Intermediate Similarity	NPC472139
0.8494	Intermediate Similarity	NPC88841
0.8494	Intermediate Similarity	NPC419
0.8494	Intermediate Similarity	NPC288602
0.8494	Intermediate Similarity	NPC234660
0.8485	Intermediate Similarity	NPC191828
0.8485	Intermediate Similarity	NPC335761
0.8476	Intermediate Similarity	NPC469847
0.8476	Intermediate Similarity	NPC187149
0.8476	Intermediate Similarity	NPC472283
0.8476	Intermediate Similarity	NPC173544
0.8466	Intermediate Similarity	NPC469850
0.8466	Intermediate Similarity	NPC296807
0.8466	Intermediate Similarity	NPC155939
0.8466	Intermediate Similarity	NPC141538
0.8462	Intermediate Similarity	NPC82602
0.8462	Intermediate Similarity	NPC472650
0.8457	Intermediate Similarity	NPC33938
0.8457	Intermediate Similarity	NPC470996
0.8457	Intermediate Similarity	NPC268905
0.8452	Intermediate Similarity	NPC270312
0.8447	Intermediate Similarity	NPC476122
0.8447	Intermediate Similarity	NPC470997
0.8443	Intermediate Similarity	NPC261184
0.8434	Intermediate Similarity	NPC207978
0.8434	Intermediate Similarity	NPC117986
0.8434	Intermediate Similarity	NPC18347
0.8434	Intermediate Similarity	NPC149896
0.8434	Intermediate Similarity	NPC211777
0.8434	Intermediate Similarity	NPC68848
0.8424	Intermediate Similarity	NPC307383
0.8421	Intermediate Similarity	NPC477824
0.8415	Intermediate Similarity	NPC263265
0.8415	Intermediate Similarity	NPC126723
0.8412	Intermediate Similarity	NPC475641
0.8412	Intermediate Similarity	NPC160818
0.8412	Intermediate Similarity	NPC475237
0.8412	Intermediate Similarity	NPC169299
0.8405	Intermediate Similarity	NPC237259
0.8405	Intermediate Similarity	NPC98206
0.8405	Intermediate Similarity	NPC34421
0.8395	Intermediate Similarity	NPC291150
0.8385	Intermediate Similarity	NPC234494
0.8383	Intermediate Similarity	NPC469846
0.8383	Intermediate Similarity	NPC283209

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 NPC472764 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	305
0.1-0.2	1004
0.2-0.3	2320
0.3-0.4	2698
0.4-0.5	1809
0.5-0.6	774
0.6-0.7	222
0.7-0.8	16
0.8-0.85	0
0.85-0.9	2
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8812	High Similarity	NPD5760	Phase 2
0.8812	High Similarity	NPD5761	Phase 2
0.8034	Intermediate Similarity	NPD8434	Phase 2
0.7941	Intermediate Similarity	NPD5537	Clinical (unspecified phase)
0.7853	Intermediate Similarity	NPD6765	Approved
0.7853	Intermediate Similarity	NPD6764	Approved
0.768	Intermediate Similarity	NPD6785	Approved
0.768	Intermediate Similarity	NPD6784	Approved
0.7299	Intermediate Similarity	NPD7819	Suspended
0.7204	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.72	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7175	Intermediate Similarity	NPD7075	Discontinued
0.7174	Intermediate Similarity	NPD6559	Discontinued
0.7151	Intermediate Similarity	NPD920	Approved
0.7101	Intermediate Similarity	NPD4628	Phase 3
0.7095	Intermediate Similarity	NPD5494	Approved
0.7086	Intermediate Similarity	NPD7411	Suspended
0.7081	Intermediate Similarity	NPD7685	Pre-registration
0.7062	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7056	Intermediate Similarity	NPD1247	Approved
0.7056	Intermediate Similarity	NPD8127	Discontinued
0.7049	Intermediate Similarity	NPD7799	Discontinued
0.7039	Intermediate Similarity	NPD919	Approved
0.7035	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7029	Intermediate Similarity	NPD6599	Discontinued
0.7024	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.7024	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.7024	Intermediate Similarity	NPD6004	Phase 3
0.7024	Intermediate Similarity	NPD6005	Phase 3
0.7024	Intermediate Similarity	NPD6002	Phase 3
0.6994	Remote Similarity	NPD6273	Approved
0.6983	Remote Similarity	NPD3749	Approved
0.6961	Remote Similarity	NPD7199	Phase 2
0.6957	Remote Similarity	NPD3818	Discontinued
0.6949	Remote Similarity	NPD6801	Discontinued
0.6932	Remote Similarity	NPD4380	Phase 2
0.6927	Remote Similarity	NPD8404	Phase 2
0.6927	Remote Similarity	NPD4868	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD2343	Clinical (unspecified phase)
0.6919	Remote Similarity	NPD5844	Phase 1
0.6919	Remote Similarity	NPD7236	Approved
0.6919	Remote Similarity	NPD643	Clinical (unspecified phase)
0.691	Remote Similarity	NPD2393	Clinical (unspecified phase)
0.6905	Remote Similarity	NPD2799	Discontinued
0.6902	Remote Similarity	NPD7473	Discontinued
0.6889	Remote Similarity	NPD4381	Clinical (unspecified phase)
0.6879	Remote Similarity	NPD6799	Approved
0.6875	Remote Similarity	NPD3226	Approved
0.6872	Remote Similarity	NPD3817	Phase 2
0.6854	Remote Similarity	NPD1934	Approved
0.6848	Remote Similarity	NPD7852	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6839	Remote Similarity	NPD2534	Approved
0.6839	Remote Similarity	NPD2532	Approved
0.6839	Remote Similarity	NPD7879	Clinical (unspecified phase)
0.6839	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6839	Remote Similarity	NPD2533	Approved
0.6834	Remote Similarity	NPD7497	Discontinued
0.6833	Remote Similarity	NPD3882	Suspended
0.6818	Remote Similarity	NPD7239	Suspended
0.6802	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6793	Remote Similarity	NPD7184	Clinical (unspecified phase)
0.6791	Remote Similarity	NPD7074	Phase 3
0.6778	Remote Similarity	NPD5402	Approved
0.6757	Remote Similarity	NPD6167	Clinical (unspecified phase)
0.6757	Remote Similarity	NPD6166	Phase 2
0.6757	Remote Similarity	NPD6168	Clinical (unspecified phase)
0.6755	Remote Similarity	NPD7993	Clinical (unspecified phase)
0.6744	Remote Similarity	NPD1243	Approved
0.6744	Remote Similarity	NPD2800	Approved
0.674	Remote Similarity	NPD4966	Approved
0.674	Remote Similarity	NPD4967	Phase 2
0.674	Remote Similarity	NPD4965	Approved
0.6739	Remote Similarity	NPD6232	Discontinued
0.6738	Remote Similarity	NPD7804	Clinical (unspecified phase)
0.6738	Remote Similarity	NPD7054	Approved
0.6737	Remote Similarity	NPD8313	Approved
0.6737	Remote Similarity	NPD8312	Approved
0.6725	Remote Similarity	NPD5762	Approved
0.6725	Remote Similarity	NPD1471	Phase 3
0.6725	Remote Similarity	NPD5763	Approved
0.6707	Remote Similarity	NPD5647	Approved
0.6707	Remote Similarity	NPD6007	Clinical (unspecified phase)
0.6703	Remote Similarity	NPD3926	Phase 2
0.6702	Remote Similarity	NPD7472	Approved
0.6686	Remote Similarity	NPD6653	Approved
0.6686	Remote Similarity	NPD970	Clinical (unspecified phase)
0.6686	Remote Similarity	NPD1549	Phase 2
0.6684	Remote Similarity	NPD7893	Clinical (unspecified phase)
0.6684	Remote Similarity	NPD4338	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD2796	Approved
0.6667	Remote Similarity	NPD5403	Approved
0.6667	Remote Similarity	NPD37	Approved
0.6648	Remote Similarity	NPD5401	Approved
0.6648	Remote Similarity	NPD4378	Clinical (unspecified phase)
0.6632	Remote Similarity	NPD8150	Discontinued
0.6632	Remote Similarity	NPD7251	Discontinued
0.663	Remote Similarity	NPD2801	Approved
0.6628	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.6628	Remote Similarity	NPD2346	Discontinued
0.6628	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6609	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.6608	Remote Similarity	NPD7033	Discontinued
0.6597	Remote Similarity	NPD7808	Phase 3
0.6596	Remote Similarity	NPD7228	Approved
0.6596	Remote Similarity	NPD3751	Discontinued
0.6595	Remote Similarity	NPD6959	Discontinued
0.6579	Remote Similarity	NPD6797	Phase 2
0.6576	Remote Similarity	NPD6234	Discontinued
0.6573	Remote Similarity	NPD6980	Clinical (unspecified phase)
0.657	Remote Similarity	NPD6100	Approved
0.657	Remote Similarity	NPD6099	Approved
0.657	Remote Similarity	NPD1551	Phase 2
0.6559	Remote Similarity	NPD3787	Discontinued
0.6557	Remote Similarity	NPD7768	Phase 2
0.6556	Remote Similarity	NPD7028	Phase 2
0.6554	Remote Similarity	NPD7410	Clinical (unspecified phase)
0.6548	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6538	Remote Similarity	NPD1465	Phase 2
0.6532	Remote Similarity	NPD2344	Approved
0.6529	Remote Similarity	NPD447	Suspended
0.6529	Remote Similarity	NPD6355	Discontinued
0.6528	Remote Similarity	NPD8407	Phase 2
0.6527	Remote Similarity	NPD6832	Phase 2
0.6514	Remote Similarity	NPD3750	Approved
0.6502	Remote Similarity	NPD7435	Discontinued
0.65	Remote Similarity	NPD7458	Discontinued
0.65	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6489	Remote Similarity	NPD2403	Approved
0.6474	Remote Similarity	NPD2935	Discontinued
0.6471	Remote Similarity	NPD5711	Approved
0.6471	Remote Similarity	NPD4140	Approved
0.6471	Remote Similarity	NPD6808	Phase 2
0.6471	Remote Similarity	NPD7229	Phase 3
0.6471	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.6471	Remote Similarity	NPD5710	Approved
0.6471	Remote Similarity	NPD7315	Approved
0.6467	Remote Similarity	NPD7057	Phase 3
0.6467	Remote Similarity	NPD7058	Phase 2
0.6458	Remote Similarity	NPD8368	Discontinued
0.6458	Remote Similarity	NPD7240	Approved
0.645	Remote Similarity	NPD3268	Approved
0.645	Remote Similarity	NPD2313	Discontinued
0.6446	Remote Similarity	NPD6362	Approved
0.642	Remote Similarity	NPD4110	Phase 3
0.642	Remote Similarity	NPD4109	Clinical (unspecified phase)
0.6416	Remote Similarity	NPD1510	Phase 2
0.6416	Remote Similarity	NPD3748	Approved
0.6413	Remote Similarity	NPD5353	Approved
0.6406	Remote Similarity	NPD5953	Discontinued
0.6404	Remote Similarity	NPD1511	Approved
0.6404	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6402	Remote Similarity	NPD7907	Approved
0.64	Remote Similarity	NPD2424	Discontinued
0.6396	Remote Similarity	NPD8397	Clinical (unspecified phase)
0.6395	Remote Similarity	NPD6651	Approved
0.6387	Remote Similarity	NPD7286	Phase 2
0.6386	Remote Similarity	NPD8285	Discontinued
0.6385	Remote Similarity	NPD4111	Phase 1
0.6385	Remote Similarity	NPD4665	Approved
0.6384	Remote Similarity	NPD2309	Approved
0.6374	Remote Similarity	NPD1240	Approved
0.6364	Remote Similarity	NPD1608	Approved
0.6359	Remote Similarity	NPD8455	Phase 2
0.6358	Remote Similarity	NPD7097	Phase 1
0.6355	Remote Similarity	NPD6776	Approved
0.6355	Remote Similarity	NPD6782	Approved
0.6355	Remote Similarity	NPD6777	Approved
0.6355	Remote Similarity	NPD6779	Approved
0.6355	Remote Similarity	NPD6778	Approved
0.6355	Remote Similarity	NPD6781	Approved
0.6355	Remote Similarity	NPD6780	Approved
0.6355	Remote Similarity	NPD7501	Clinical (unspecified phase)
0.6351	Remote Similarity	NPD7930	Approved
0.6347	Remote Similarity	NPD7319	Approved
0.6343	Remote Similarity	NPD5619	Clinical (unspecified phase)
0.6341	Remote Similarity	NPD7696	Phase 3
0.6341	Remote Similarity	NPD7697	Approved
0.6341	Remote Similarity	NPD7698	Approved
0.6337	Remote Similarity	NPD230	Phase 1
0.6337	Remote Similarity	NPD5735	Approved
0.6333	Remote Similarity	NPD1512	Approved
0.6333	Remote Similarity	NPD7314	Clinical (unspecified phase)
0.6316	Remote Similarity	NPD8032	Phase 2
0.6316	Remote Similarity	NPD7874	Approved
0.6316	Remote Similarity	NPD7875	Clinical (unspecified phase)
0.6311	Remote Similarity	NPD7870	Phase 2
0.6311	Remote Similarity	NPD7871	Phase 2
0.6301	Remote Similarity	NPD1607	Approved
0.6292	Remote Similarity	NPD6190	Approved
0.6275	Remote Similarity	NPD4107	Approved
0.6268	Remote Similarity	NPD8151	Discontinued
0.6265	Remote Similarity	NPD9717	Approved
0.6257	Remote Similarity	NPD1699	Clinical (unspecified phase)
0.6257	Remote Similarity	NPD3764	Approved
0.6256	Remote Similarity	NPD4419	Clinical (unspecified phase)
0.625	Remote Similarity	NPD2163	Approved
0.625	Remote Similarity	NPD3267	Approved
0.625	Remote Similarity	NPD3266	Approved
0.625	Remote Similarity	NPD7615	Clinical (unspecified phase)

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