NPASS Compound

Structure

NPC471437 OpenBabel07101719252D 40 45 0 0 1 0 0 0 0 0999 V2000 1.9890 -0.2091 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1369 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8945 -1.6406 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1756 -1.6180 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5743 -3.9360 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4049 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1075 -0.4945 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 -6.0856 -0.7024 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4049 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.9165 0.9067 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9511 -0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5823 0.7045 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0029 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5388 -0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.4049 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2709 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8978 -0.3141 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.3090 -2.5691 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0000 -1.6180 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.5878 0.8090 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.2129 -1.2567 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1369 1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.2872 -2.7770 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2709 0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.9511 -1.3090 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.5878 -0.8090 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.5388 0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.1701 1.5135 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.2709 3.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.8817 -0.4927 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.3601 -3.3122 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.6868 -2.1373 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.9563 -2.0339 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.9456 1.4135 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.5962 -3.7281 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.5856 0.1636 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.1369 2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.5878 0.8090 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 13 1 0 0 0 0 4 27 1 0 0 0 0 5 37 1 0 0 0 0 6 8 1 0 0 0 0 6 15 1 0 0 0 0 7 9 2 0 0 0 0 7 14 1 0 0 0 0 8 25 1 0 0 0 0 9 38 1 0 0 0 0 10 16 2 0 0 0 0 10 17 1 0 0 0 0 11 14 2 0 0 0 0 11 38 1 0 0 0 0 12 26 1 0 0 0 0 12 28 1 0 0 0 0 13 30 2 0 0 0 0 13 40 1 0 0 0 0 14 23 1 0 0 0 0 15 27 1 1 0 0 0 15 29 1 0 0 0 0 16 25 1 0 0 0 0 16 29 1 0 0 0 0 17 31 2 0 0 0 0 17 39 1 0 0 0 0 18 21 1 0 0 0 0 18 22 1 0 0 0 0 18 32 1 6 0 0 0 19 20 1 0 0 0 0 19 24 1 0 0 0 0 19 33 1 1 0 0 0 20 26 1 6 0 0 0 20 27 1 0 0 0 0 21 28 1 6 0 0 0 21 29 1 0 0 0 0 22 26 1 0 0 0 0 22 34 2 0 0 0 0 23 25 1 6 0 0 0 23 39 1 0 0 0 0 24 35 2 0 0 0 0 24 37 1 0 0 0 0 25 2 1 6 0 0 0 26 3 1 6 0 0 0 27 28 1 6 0 0 0 28 40 1 6 0 0 0 29 36 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	558.21
Volume:	537.039
LogP:	1.407
LogD:	0.57
LogS:	-3.326
# Rotatable Bonds:	6
TPSA:	169.8
# H-Bond Aceptor:	11
# H-Bond Donor:	3
# Rings:	6
# Heavy Atoms:	11

MedChem Properties

QED Drug-Likeness Score:	0.36
Synthetic Accessibility Score:	6.405
Fsp3:	0.655
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:	-5.432
MDCK Permeability:	5.432952457340434e-05
Pgp-inhibitor:	0.868
Pgp-substrate:	0.96
Human Intestinal Absorption (HIA):	0.777
20% Bioavailability (F20%):	0.941
30% Bioavailability (F30%):	0.771

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.447
Plasma Protein Binding (PPB):	67.92583465576172%
Volume Distribution (VD):	0.833
Pgp-substrate:	29.672348022460938%

ADMET: Metabolism

CYP1A2-inhibitor:	0.002
CYP1A2-substrate:	0.866
CYP2C19-inhibitor:	0.033
CYP2C19-substrate:	0.473
CYP2C9-inhibitor:	0.081
CYP2C9-substrate:	0.027
CYP2D6-inhibitor:	0.004
CYP2D6-substrate:	0.067
CYP3A4-inhibitor:	0.793
CYP3A4-substrate:	0.396

ADMET: Excretion

Clearance (CL):	2.014
Half-life (T1/2):	0.373

ADMET: Toxicity

hERG Blockers:	0.074
Human Hepatotoxicity (H-HT):	0.312
Drug-inuced Liver Injury (DILI):	0.28
AMES Toxicity:	0.111
Rat Oral Acute Toxicity:	0.993
Maximum Recommended Daily Dose:	0.53
Skin Sensitization:	0.06
Carcinogencity:	0.231
Eye Corrosion:	0.003
Eye Irritation:	0.011
Respiratory Toxicity:	0.983

Download Data

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

Natural Product: NPC471437

Natural Product ID:	NPC471437
*Common Name:**	HNJAWPSGFNODRH-WGTDDYQRSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	HNJAWPSGFNODRH-WGTDDYQRSA-N
Standard InCHI:	InChI=1S/C29H34O11/c1-13(30)40-28-12-26(3)20(19(33)24(35)37-5)27(28,4)15-6-8-25(2)16(29(15,36)21(28)18(32)22(26)34)10-17(31)39-23(25)14-7-9-38-11-14/h7,9-11,15,18-21,23,32-33,36H,6,8,12H2,1-5H3/t15-,18-,19-,20+,21+,23+,25-,26+,27-,28+,29+/m1/s1
SMILES:	CC(=O)OC12CC3(C(C1(C4CCC5(C(OC(=O)C=C5C4(C2C(C3=O)O)O)C6=COC=C6)C)C)C(C(=O)OC)O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2448528
PubChem CID:	71718798
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000264] Organic acids and derivatives [CHEMONTID:0000265] Carboxylic acids and derivatives [CHEMONTID:0001986] Tricarboxylic 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
NPO6774	Khaya senegalensis	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12193039]
NPO6774	Khaya senegalensis	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23210623]
NPO6774	Khaya senegalensis	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
MIC	4

Activity Type	# Activity
Organism	4

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	>	50.0	ug.mL-1	PMID[448649]
NPT18	Organism	Pseudomonas aeruginosa	Pseudomonas aeruginosa	MIC	>	50.0	ug.mL-1	PMID[448649]

☑ 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 NPC471437 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	379
0.1-0.2	1420
0.2-0.3	3288
0.3-0.4	5732
0.4-0.5	11062
0.5-0.6	10212
0.6-0.7	9023
0.7-0.8	1204
0.8-0.85	265
0.85-0.9	91
0.9-0.95	19
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9398	High Similarity	NPC478177
0.9277	High Similarity	NPC469576
0.9277	High Similarity	NPC236004
0.9277	High Similarity	NPC94763
0.9273	High Similarity	NPC285227
0.9222	High Similarity	NPC469633
0.9198	High Similarity	NPC329938
0.9172	High Similarity	NPC470938
0.9152	High Similarity	NPC472766
0.9152	High Similarity	NPC472765
0.9146	High Similarity	NPC149945
0.9141	High Similarity	NPC165218
0.9136	High Similarity	NPC477402
0.9091	High Similarity	NPC472764
0.9068	High Similarity	NPC469485
0.9048	High Similarity	NPC471632
0.903	High Similarity	NPC478178
0.9024	High Similarity	NPC477405
0.9024	High Similarity	NPC663
0.9024	High Similarity	NPC224394
0.9012	High Similarity	NPC105395
0.9012	High Similarity	NPC173544
0.9012	High Similarity	NPC247563
0.9012	High Similarity	NPC242068
0.8976	High Similarity	NPC472775
0.8976	High Similarity	NPC472774
0.8976	High Similarity	NPC478179
0.897	High Similarity	NPC123088
0.897	High Similarity	NPC276551
0.897	High Similarity	NPC470940
0.8963	High Similarity	NPC69028
0.8963	High Similarity	NPC263432
0.8963	High Similarity	NPC472767
0.8963	High Similarity	NPC193798
0.8957	High Similarity	NPC477403
0.8929	High Similarity	NPC159232
0.8922	High Similarity	NPC471397
0.8922	High Similarity	NPC327922
0.8916	High Similarity	NPC470875
0.8916	High Similarity	NPC214600
0.8909	High Similarity	NPC292389
0.8909	High Similarity	NPC469338
0.8909	High Similarity	NPC472773
0.8902	High Similarity	NPC25255
0.8876	High Similarity	NPC469848
0.8869	High Similarity	NPC472659
0.8862	High Similarity	NPC476850
0.8862	High Similarity	NPC173516
0.8862	High Similarity	NPC472282
0.8862	High Similarity	NPC476861
0.8862	High Similarity	NPC476224
0.8855	High Similarity	NPC476857
0.8855	High Similarity	NPC476858
0.8855	High Similarity	NPC469849
0.8855	High Similarity	NPC476856
0.8848	High Similarity	NPC472771
0.8848	High Similarity	NPC82851
0.8848	High Similarity	NPC6326
0.8841	High Similarity	NPC475967
0.881	High Similarity	NPC160651
0.8795	High Similarity	NPC471168
0.8788	High Similarity	NPC470789
0.878	High Similarity	NPC195131
0.878	High Similarity	NPC45101
0.878	High Similarity	NPC472772
0.878	High Similarity	NPC249021
0.878	High Similarity	NPC261597
0.878	High Similarity	NPC36655
0.8773	High Similarity	NPC264943
0.8757	High Similarity	NPC470995
0.875	High Similarity	NPC476853
0.8735	High Similarity	NPC470792
0.8735	High Similarity	NPC197596
0.8735	High Similarity	NPC471166
0.8735	High Similarity	NPC471167
0.8735	High Similarity	NPC200782
0.8727	High Similarity	NPC475226
0.872	High Similarity	NPC204663
0.8698	High Similarity	NPC271235
0.869	High Similarity	NPC23387
0.869	High Similarity	NPC472141
0.8683	High Similarity	NPC39986
0.8683	High Similarity	NPC134254
0.8683	High Similarity	NPC302369
0.8675	High Similarity	NPC191828
0.8667	High Similarity	NPC472776
0.8667	High Similarity	NPC472778
0.8667	High Similarity	NPC472777
0.8667	High Similarity	NPC197137
0.8659	High Similarity	NPC44675
0.8659	High Similarity	NPC281258
0.8659	High Similarity	NPC92979
0.8659	High Similarity	NPC214541
0.8659	High Similarity	NPC469336
0.865	High Similarity	NPC75906
0.8639	High Similarity	NPC472651
0.8631	High Similarity	NPC261184
0.8631	High Similarity	NPC476860
0.8623	High Similarity	NPC470939
0.8623	High Similarity	NPC5741
0.8623	High Similarity	NPC472668
0.8623	High Similarity	NPC5079
0.8614	High Similarity	NPC307383
0.8614	High Similarity	NPC237155
0.8598	High Similarity	NPC282445
0.8598	High Similarity	NPC178932
0.8588	High Similarity	NPC472652
0.858	High Similarity	NPC472654
0.858	High Similarity	NPC121995
0.8571	High Similarity	NPC51568
0.8571	High Similarity	NPC88841
0.8571	High Similarity	NPC234660
0.8571	High Similarity	NPC472669
0.8571	High Similarity	NPC288602
0.8563	High Similarity	NPC472653
0.8563	High Similarity	NPC305016
0.8563	High Similarity	NPC335761
0.8554	High Similarity	NPC187149
0.8554	High Similarity	NPC167142
0.8554	High Similarity	NPC470118
0.8554	High Similarity	NPC472283
0.8554	High Similarity	NPC299038
0.8545	High Similarity	NPC296807
0.8545	High Similarity	NPC35000
0.8545	High Similarity	NPC141538
0.8545	High Similarity	NPC155939
0.8538	High Similarity	NPC82602
0.8537	High Similarity	NPC33938
0.8537	High Similarity	NPC469503
0.8537	High Similarity	NPC470996
0.8521	High Similarity	NPC470182
0.8521	High Similarity	NPC271657
0.8512	High Similarity	NPC117986
0.8512	High Similarity	NPC207978
0.8512	High Similarity	NPC18986
0.8512	High Similarity	NPC188649
0.8506	High Similarity	NPC470181
0.8503	High Similarity	NPC472671
0.8503	High Similarity	NPC472779
0.8494	Intermediate Similarity	NPC263265
0.8494	Intermediate Similarity	NPC60973
0.8488	Intermediate Similarity	NPC169299
0.8488	Intermediate Similarity	NPC160818
0.8485	Intermediate Similarity	NPC34421
0.8485	Intermediate Similarity	NPC98206
0.8485	Intermediate Similarity	NPC30222
0.8485	Intermediate Similarity	NPC302054
0.8485	Intermediate Similarity	NPC253201
0.8485	Intermediate Similarity	NPC237259
0.848	Intermediate Similarity	NPC472673
0.8476	Intermediate Similarity	NPC272590
0.8471	Intermediate Similarity	NPC475779
0.8466	Intermediate Similarity	NPC69647
0.8466	Intermediate Similarity	NPC195325
0.8466	Intermediate Similarity	NPC125182
0.8462	Intermediate Similarity	NPC419
0.8462	Intermediate Similarity	NPC472139
0.8443	Intermediate Similarity	NPC286722
0.8443	Intermediate Similarity	NPC470119
0.8443	Intermediate Similarity	NPC469847
0.8443	Intermediate Similarity	NPC214495
0.8443	Intermediate Similarity	NPC475066
0.8424	Intermediate Similarity	NPC44577
0.8424	Intermediate Similarity	NPC476201
0.8424	Intermediate Similarity	NPC472672
0.8415	Intermediate Similarity	NPC477404
0.8415	Intermediate Similarity	NPC159927
0.8415	Intermediate Similarity	NPC470997
0.8415	Intermediate Similarity	NPC156189
0.8415	Intermediate Similarity	NPC469335
0.8415	Intermediate Similarity	NPC196864
0.8412	Intermediate Similarity	NPC259943
0.8402	Intermediate Similarity	NPC18347
0.8402	Intermediate Similarity	NPC96443
0.8402	Intermediate Similarity	NPC149896
0.8402	Intermediate Similarity	NPC68848
0.8402	Intermediate Similarity	NPC290400
0.8393	Intermediate Similarity	NPC475295
0.8393	Intermediate Similarity	NPC473473
0.8393	Intermediate Similarity	NPC474932
0.8393	Intermediate Similarity	NPC116639
0.8391	Intermediate Similarity	NPC477824
0.8383	Intermediate Similarity	NPC126723
0.8383	Intermediate Similarity	NPC209364
0.8383	Intermediate Similarity	NPC107646
0.8382	Intermediate Similarity	NPC475237
0.8382	Intermediate Similarity	NPC475641
0.8372	Intermediate Similarity	NPC296558
0.8372	Intermediate Similarity	NPC242334
0.8364	Intermediate Similarity	NPC18135
0.8364	Intermediate Similarity	NPC116717
0.8363	Intermediate Similarity	NPC93172
0.8363	Intermediate Similarity	NPC97574
0.8354	Intermediate Similarity	NPC470998
0.8354	Intermediate Similarity	NPC234494
0.8353	Intermediate Similarity	NPC285567
0.8353	Intermediate Similarity	NPC476197
0.8353	Intermediate Similarity	NPC469846
0.8353	Intermediate Similarity	NPC283209
0.8353	Intermediate Similarity	NPC198047

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 NPC471437 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	316
0.1-0.2	993
0.2-0.3	2332
0.3-0.4	2762
0.4-0.5	1768
0.5-0.6	733
0.6-0.7	230
0.7-0.8	14
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
0.8889	High Similarity	NPD5760	Phase 2
0.8889	High Similarity	NPD5761	Phase 2
0.8315	Intermediate Similarity	NPD8434	Phase 2
0.8034	Intermediate Similarity	NPD6764	Approved
0.8034	Intermediate Similarity	NPD6765	Approved
0.7919	Intermediate Similarity	NPD5537	Clinical (unspecified phase)
0.7857	Intermediate Similarity	NPD6785	Approved
0.7857	Intermediate Similarity	NPD6784	Approved
0.736	Intermediate Similarity	NPD7075	Discontinued
0.733	Intermediate Similarity	NPD6801	Discontinued
0.7288	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7287	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7258	Intermediate Similarity	NPD6559	Discontinued
0.7247	Intermediate Similarity	NPD5402	Approved
0.7228	Intermediate Similarity	NPD7799	Discontinued
0.7216	Intermediate Similarity	NPD6599	Discontinued
0.7193	Intermediate Similarity	NPD4628	Phase 3
0.7171	Intermediate Similarity	NPD8404	Phase 2
0.7143	Intermediate Similarity	NPD5403	Approved
0.711	Intermediate Similarity	NPD7236	Approved
0.7098	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7095	Intermediate Similarity	NPD7819	Suspended
0.7074	Intermediate Similarity	NPD7685	Pre-registration
0.7062	Intermediate Similarity	NPD3226	Approved
0.7056	Intermediate Similarity	NPD3817	Phase 2
0.7043	Intermediate Similarity	NPD3818	Discontinued
0.7029	Intermediate Similarity	NPD5401	Approved
0.7022	Intermediate Similarity	NPD4380	Phase 2
0.7018	Intermediate Similarity	NPD5762	Approved
0.7018	Intermediate Similarity	NPD5763	Approved
0.7006	Intermediate Similarity	NPD7239	Suspended
0.7005	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.6989	Remote Similarity	NPD6273	Approved
0.6983	Remote Similarity	NPD7411	Suspended
0.6978	Remote Similarity	NPD4381	Clinical (unspecified phase)
0.6971	Remote Similarity	NPD6799	Approved
0.6961	Remote Similarity	NPD8443	Clinical (unspecified phase)
0.6957	Remote Similarity	NPD8127	Discontinued
0.6957	Remote Similarity	NPD1247	Approved
0.6949	Remote Similarity	NPD920	Approved
0.694	Remote Similarity	NPD919	Approved
0.6932	Remote Similarity	NPD4378	Clinical (unspecified phase)
0.6932	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD3882	Suspended
0.6919	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.6919	Remote Similarity	NPD6005	Phase 3
0.6919	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.6919	Remote Similarity	NPD6004	Phase 3
0.6919	Remote Similarity	NPD6002	Phase 3
0.6911	Remote Similarity	NPD8313	Approved
0.6911	Remote Similarity	NPD8312	Approved
0.6898	Remote Similarity	NPD7473	Discontinued
0.6891	Remote Similarity	NPD8150	Discontinued
0.6885	Remote Similarity	NPD3749	Approved
0.6882	Remote Similarity	NPD7184	Clinical (unspecified phase)
0.6865	Remote Similarity	NPD7199	Phase 2
0.6859	Remote Similarity	NPD4338	Clinical (unspecified phase)
0.6845	Remote Similarity	NPD6168	Clinical (unspecified phase)
0.6845	Remote Similarity	NPD6167	Clinical (unspecified phase)
0.6845	Remote Similarity	NPD6166	Phase 2
0.6839	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6836	Remote Similarity	NPD642	Clinical (unspecified phase)
0.6832	Remote Similarity	NPD7497	Discontinued
0.6831	Remote Similarity	NPD4868	Clinical (unspecified phase)
0.6825	Remote Similarity	NPD5844	Phase 1
0.6821	Remote Similarity	NPD2343	Clinical (unspecified phase)
0.6821	Remote Similarity	NPD1471	Phase 3
0.6813	Remote Similarity	NPD2393	Clinical (unspecified phase)
0.6811	Remote Similarity	NPD5494	Approved
0.6806	Remote Similarity	NPD7251	Discontinued
0.6802	Remote Similarity	NPD7033	Discontinued
0.68	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6771	Remote Similarity	NPD7808	Phase 3
0.6758	Remote Similarity	NPD1934	Approved
0.6755	Remote Similarity	NPD7852	Clinical (unspecified phase)
0.6754	Remote Similarity	NPD7993	Clinical (unspecified phase)
0.6754	Remote Similarity	NPD6797	Phase 2
0.6749	Remote Similarity	NPD7435	Discontinued
0.6742	Remote Similarity	NPD2534	Approved
0.6742	Remote Similarity	NPD2533	Approved
0.6742	Remote Similarity	NPD2532	Approved
0.6739	Remote Similarity	NPD4965	Approved
0.6739	Remote Similarity	NPD4967	Phase 2
0.6739	Remote Similarity	NPD4966	Approved
0.6738	Remote Similarity	NPD6232	Discontinued
0.6737	Remote Similarity	NPD7054	Approved
0.6723	Remote Similarity	NPD643	Clinical (unspecified phase)
0.6721	Remote Similarity	NPD2801	Approved
0.6707	Remote Similarity	NPD5647	Approved
0.6707	Remote Similarity	NPD6007	Clinical (unspecified phase)
0.6702	Remote Similarity	NPD7472	Approved
0.6702	Remote Similarity	NPD7074	Phase 3
0.6701	Remote Similarity	NPD8407	Phase 2
0.6686	Remote Similarity	NPD6653	Approved
0.6684	Remote Similarity	NPD3751	Discontinued
0.6667	Remote Similarity	NPD2796	Approved
0.6667	Remote Similarity	NPD6099	Approved
0.6667	Remote Similarity	NPD6234	Discontinued
0.6667	Remote Similarity	NPD37	Approved
0.6667	Remote Similarity	NPD1551	Phase 2
0.6667	Remote Similarity	NPD6100	Approved
0.6649	Remote Similarity	NPD7057	Phase 3
0.6649	Remote Similarity	NPD7058	Phase 2
0.6648	Remote Similarity	NPD7410	Clinical (unspecified phase)
0.6647	Remote Similarity	NPD3268	Approved
0.6632	Remote Similarity	NPD8368	Discontinued
0.6629	Remote Similarity	NPD2346	Discontinued
0.6628	Remote Similarity	NPD6355	Discontinued
0.6614	Remote Similarity	NPD3926	Phase 2
0.6611	Remote Similarity	NPD1512	Approved
0.661	Remote Similarity	NPD3750	Approved
0.6601	Remote Similarity	NPD6782	Approved
0.6601	Remote Similarity	NPD6778	Approved
0.6601	Remote Similarity	NPD6777	Approved
0.6601	Remote Similarity	NPD6776	Approved
0.6601	Remote Similarity	NPD6779	Approved
0.6601	Remote Similarity	NPD6781	Approved
0.6601	Remote Similarity	NPD6780	Approved
0.6597	Remote Similarity	NPD7228	Approved
0.6597	Remote Similarity	NPD7893	Clinical (unspecified phase)
0.6596	Remote Similarity	NPD6959	Discontinued
0.6593	Remote Similarity	NPD7458	Discontinued
0.6593	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6591	Remote Similarity	NPD970	Clinical (unspecified phase)
0.6591	Remote Similarity	NPD1549	Phase 2
0.6561	Remote Similarity	NPD3787	Discontinued
0.6559	Remote Similarity	NPD7768	Phase 2
0.6555	Remote Similarity	NPD7874	Approved
0.6555	Remote Similarity	NPD7875	Clinical (unspecified phase)
0.6554	Remote Similarity	NPD1243	Approved
0.6554	Remote Similarity	NPD2800	Approved
0.655	Remote Similarity	NPD2313	Discontinued
0.6535	Remote Similarity	NPD8090	Clinical (unspecified phase)
0.6534	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.6534	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6532	Remote Similarity	NPD5735	Approved
0.6517	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.6514	Remote Similarity	NPD2799	Discontinued
0.6514	Remote Similarity	NPD1510	Phase 2
0.6505	Remote Similarity	NPD7697	Approved
0.6505	Remote Similarity	NPD7696	Phase 3
0.6505	Remote Similarity	NPD7698	Approved
0.65	Remote Similarity	NPD1511	Approved
0.6482	Remote Similarity	NPD8361	Approved
0.6482	Remote Similarity	NPD8397	Clinical (unspecified phase)
0.6482	Remote Similarity	NPD8360	Approved
0.6481	Remote Similarity	NPD7907	Approved
0.648	Remote Similarity	NPD6190	Approved
0.6474	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.6474	Remote Similarity	NPD4140	Approved
0.6473	Remote Similarity	NPD7871	Phase 2
0.6473	Remote Similarity	NPD8320	Phase 1
0.6473	Remote Similarity	NPD8319	Approved
0.6473	Remote Similarity	NPD7870	Phase 2
0.6471	Remote Similarity	NPD8285	Discontinued
0.6467	Remote Similarity	NPD7028	Phase 2
0.6465	Remote Similarity	NPD4665	Approved
0.6465	Remote Similarity	NPD4111	Phase 1
0.6459	Remote Similarity	NPD7701	Phase 2
0.6452	Remote Similarity	NPD1465	Phase 2
0.6445	Remote Similarity	NPD7801	Approved
0.6441	Remote Similarity	NPD2344	Approved
0.6433	Remote Similarity	NPD6832	Phase 2
0.6422	Remote Similarity	NPD5619	Clinical (unspecified phase)
0.642	Remote Similarity	NPD4308	Phase 3
0.642	Remote Similarity	NPD3748	Approved
0.6416	Remote Similarity	NPD6663	Approved
0.6406	Remote Similarity	NPD4575	Clinical (unspecified phase)
0.64	Remote Similarity	NPD8435	Approved
0.6393	Remote Similarity	NPD6980	Clinical (unspecified phase)
0.6387	Remote Similarity	NPD7315	Approved
0.6387	Remote Similarity	NPD7229	Phase 3
0.6384	Remote Similarity	NPD2935	Discontinued
0.6378	Remote Similarity	NPD7240	Approved
0.6358	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6355	Remote Similarity	NPD7930	Approved
0.6355	Remote Similarity	NPD6534	Approved
0.6355	Remote Similarity	NPD6535	Approved
0.6353	Remote Similarity	NPD3267	Approved
0.6353	Remote Similarity	NPD7319	Approved
0.6353	Remote Similarity	NPD3266	Approved
0.6353	Remote Similarity	NPD2797	Approved
0.6345	Remote Similarity	NPD4419	Clinical (unspecified phase)
0.6343	Remote Similarity	NPD447	Suspended
0.6341	Remote Similarity	NPD7699	Phase 2
0.6341	Remote Similarity	NPD7700	Phase 2
0.6331	Remote Similarity	NPD7078	Approved
0.6327	Remote Similarity	NPD5953	Discontinued
0.6322	Remote Similarity	NPD8032	Phase 2
0.6321	Remote Similarity	NPD7784	Clinical (unspecified phase)
0.6321	Remote Similarity	NPD2403	Approved
0.6319	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6308	Remote Similarity	NPD7286	Phase 2
0.6307	Remote Similarity	NPD1607	Approved
0.6307	Remote Similarity	NPD6353	Approved
0.6302	Remote Similarity	NPD6808	Phase 2
0.6302	Remote Similarity	NPD5710	Approved
0.6302	Remote Similarity	NPD5711	Approved
0.6301	Remote Similarity	NPD7095	Approved
0.6298	Remote Similarity	NPD3057	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