NPASS Compound

Structure

NPC470940 OpenBabel07101719252D 42 46 0 0 1 0 0 0 0 0999 V2000 3.7482 2.1640 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7159 -1.2761 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0545 0.1792 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6217 -0.5704 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7482 0.4328 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4488 2.1100 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.8441 2.6113 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2886 -0.3521 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.8678 0.2912 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2489 -1.2984 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.6849 3.3745 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7496 -0.4328 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9985 0.8656 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5883 0.8609 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9985 2.5968 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0898 -1.5923 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4978 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4993 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2489 -0.4328 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.2489 1.2984 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.2387 0.8446 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 8.3616 2.8348 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9985 -1.7312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4993 0.8656 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.7482 -0.4328 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.0000 0.8656 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6376 -0.1967 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.1889 0.1792 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9985 0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.7496 1.2984 0.0000 C 0 0 2 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 2.9985 3.4624 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.2189 -2.4482 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 8.2326 1.9789 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.9985 -2.5968 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.7496 1.2984 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8533 -0.1453 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 9.1674 3.1510 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.4350 1.0408 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.2489 2.1640 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.7666 -1.0526 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.7482 -1.2984 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 15 1 0 0 0 0 2 16 1 0 0 0 0 3 28 1 0 0 0 0 4 28 1 0 0 0 0 7 38 1 0 0 0 0 8 9 2 0 0 0 0 8 17 1 0 0 0 0 9 39 1 0 0 0 0 10 19 1 0 0 0 0 10 23 1 0 0 0 0 11 21 1 0 0 0 0 11 22 1 0 0 0 0 12 18 2 0 0 0 0 12 31 1 0 0 0 0 13 20 1 0 0 0 0 13 29 1 0 0 0 0 14 17 2 0 0 0 0 14 39 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 19 1 0 0 0 0 18 24 1 0 0 0 0 19 29 1 1 0 0 0 20 24 1 0 0 0 0 20 40 1 6 0 0 0 21 28 1 0 0 0 0 21 30 1 1 0 0 0 22 34 2 0 0 0 0 22 38 1 0 0 0 0 23 35 2 0 0 0 0 23 42 1 0 0 0 0 24 30 1 1 0 0 0 25 29 1 6 0 0 0 25 42 1 0 0 0 0 26 30 1 0 0 0 0 26 31 1 0 0 0 0 26 36 2 0 0 0 0 27 28 1 0 0 0 0 27 31 1 6 0 0 0 27 41 1 0 0 0 0 29 5 1 6 0 0 0 30 6 1 1 0 0 0 31 37 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	586.24
Volume:	577.551
LogP:	3.403
LogD:	2.11
LogS:	-4.631
# Rotatable Bonds:	8
TPSA:	155.64
# H-Bond Aceptor:	11
# H-Bond Donor:	1
# Rings:	5
# Heavy Atoms:	11

MedChem Properties

QED Drug-Likeness Score:	0.307
Synthetic Accessibility Score:	6.095
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:	-5.206
MDCK Permeability:	8.855316991684958e-05
Pgp-inhibitor:	1.0
Pgp-substrate:	0.789
Human Intestinal Absorption (HIA):	0.353
20% Bioavailability (F20%):	0.796
30% Bioavailability (F30%):	0.965

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.849
Plasma Protein Binding (PPB):	71.2624740600586%
Volume Distribution (VD):	0.811
Pgp-substrate:	25.012556076049805%

ADMET: Metabolism

CYP1A2-inhibitor:	0.005
CYP1A2-substrate:	0.063
CYP2C19-inhibitor:	0.126
CYP2C19-substrate:	0.092
CYP2C9-inhibitor:	0.296
CYP2C9-substrate:	0.021
CYP2D6-inhibitor:	0.016
CYP2D6-substrate:	0.05
CYP3A4-inhibitor:	0.822
CYP3A4-substrate:	0.562

ADMET: Excretion

Clearance (CL):	2.14
Half-life (T1/2):	0.294

ADMET: Toxicity

hERG Blockers:	0.003
Human Hepatotoxicity (H-HT):	0.526
Drug-inuced Liver Injury (DILI):	0.878
AMES Toxicity:	0.569
Rat Oral Acute Toxicity:	0.995
Maximum Recommended Daily Dose:	0.908
Skin Sensitization:	0.316
Carcinogencity:	0.567
Eye Corrosion:	0.711
Eye Irritation:	0.136
Respiratory Toxicity:	0.991

Download Data

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

Natural Product: NPC470940

Natural Product ID:	NPC470940
*Common Name:**	JKLCUPWPSAVXMO-VAAZOPOBSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	JKLCUPWPSAVXMO-VAAZOPOBSA-N
Standard InCHI:	InChI=1S/C31H38O11/c1-15(32)40-20-13-29(5)19(10-23(35)42-25(29)17-8-9-39-14-17)18-12-31(37)26(36)30(6,24(18)20)21(11-22(34)38-7)28(3,4)27(31)41-16(2)33/h8-9,12,14,19-21,24-25,27,37H,10-11,13H2,1-7H3/t19-,20+,21-,24+,25-,27-,29+,30-,31-/m0/s1
SMILES:	COC(=O)C[C@H]1C(C)(C)[C@H](OC(=O)C)[C@]2(C(=O)[C@]1(C)[C@H]1[C@H](OC(=O)C)C[C@@]3([C@H](C1=C2)CC(=O)O[C@H]3c1ccoc1)C)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2332198
PubChem CID:	44470604
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0001125] Steroid lactones

*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	=	25.0	ug.mL-1	PMID[495343]
NPT18	Organism	Pseudomonas aeruginosa	Pseudomonas aeruginosa	MIC	=	25.0	ug.mL-1	PMID[495343]

☑ 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 NPC470940 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	358
0.1-0.2	1396
0.2-0.3	3154
0.3-0.4	5310
0.4-0.5	9742
0.5-0.6	9842
0.6-0.7	8286
0.7-0.8	4066
0.8-0.85	304
0.85-0.9	146
0.9-0.95	83
0.95-1	10

Similarity Score	Similarity Level	Natural Product ID
0.9935	High Similarity	NPC292389
0.9935	High Similarity	NPC469338
0.987	High Similarity	NPC469849
0.987	High Similarity	NPC276551
0.9806	High Similarity	NPC470875
0.9744	High Similarity	NPC173516
0.974	High Similarity	NPC69028
0.9682	High Similarity	NPC471397
0.9677	High Similarity	NPC477405
0.9675	High Similarity	NPC477402
0.9613	High Similarity	NPC329938
0.9613	High Similarity	NPC82851
0.961	High Similarity	NPC477403
0.9557	High Similarity	NPC160651
0.9542	High Similarity	NPC264943
0.9494	High Similarity	NPC472774
0.9494	High Similarity	NPC472282
0.9494	High Similarity	NPC472775
0.9487	High Similarity	NPC263432
0.9487	High Similarity	NPC193798
0.9481	High Similarity	NPC469485
0.9427	High Similarity	NPC472773
0.9423	High Similarity	NPC25255
0.9419	High Similarity	NPC472283
0.9419	High Similarity	NPC249021
0.9419	High Similarity	NPC173544
0.9416	High Similarity	NPC469336
0.9367	High Similarity	NPC476858
0.9367	High Similarity	NPC470182
0.9367	High Similarity	NPC476856
0.9367	High Similarity	NPC476857
0.9363	High Similarity	NPC5079
0.9363	High Similarity	NPC200782
0.9363	High Similarity	NPC472771
0.9351	High Similarity	NPC178932
0.9304	High Similarity	NPC51568
0.9304	High Similarity	NPC234660
0.9299	High Similarity	NPC472653
0.9295	High Similarity	NPC261597
0.9295	High Similarity	NPC36655
0.9295	High Similarity	NPC286722
0.929	High Similarity	NPC281258
0.929	High Similarity	NPC44675
0.929	High Similarity	NPC214541
0.9281	High Similarity	NPC159927
0.9281	High Similarity	NPC469335
0.925	High Similarity	NPC476861
0.925	High Similarity	NPC476853
0.925	High Similarity	NPC476850
0.9245	High Similarity	NPC123088
0.9245	High Similarity	NPC476860
0.9241	High Similarity	NPC470939
0.9241	High Similarity	NPC149896
0.9236	High Similarity	NPC475967
0.9236	High Similarity	NPC473473
0.9236	High Similarity	NPC475295
0.9231	High Similarity	NPC60973
0.9231	High Similarity	NPC209364
0.9226	High Similarity	NPC282445
0.9207	High Similarity	NPC478177
0.9193	High Similarity	NPC271235
0.9187	High Similarity	NPC475779
0.9187	High Similarity	NPC23387
0.9182	High Similarity	NPC134254
0.9182	High Similarity	NPC663
0.9182	High Similarity	NPC39986
0.9182	High Similarity	NPC224394
0.9182	High Similarity	NPC302369
0.9177	High Similarity	NPC335761
0.9172	High Similarity	NPC472772
0.9172	High Similarity	NPC167142
0.9172	High Similarity	NPC45101
0.9167	High Similarity	NPC469850
0.9161	High Similarity	NPC44577
0.9161	High Similarity	NPC476201
0.9161	High Similarity	NPC469503
0.9156	High Similarity	NPC477404
0.9156	High Similarity	NPC196864
0.9136	High Similarity	NPC82602
0.913	High Similarity	NPC472651
0.913	High Similarity	NPC473753
0.913	High Similarity	NPC473766
0.9125	High Similarity	NPC271657
0.9119	High Similarity	NPC18347
0.9119	High Similarity	NPC290400
0.9119	High Similarity	NPC96443
0.9114	High Similarity	NPC307383
0.9114	High Similarity	NPC237155
0.9108	High Similarity	NPC107646
0.9103	High Similarity	NPC30222
0.9074	High Similarity	NPC472652
0.9062	High Similarity	NPC476197
0.9062	High Similarity	NPC198047
0.9062	High Similarity	NPC288602
0.9062	High Similarity	NPC88841
0.9057	High Similarity	NPC305016
0.9057	High Similarity	NPC475381
0.9051	High Similarity	NPC299038
0.9051	High Similarity	NPC187149
0.9045	High Similarity	NPC476262
0.9045	High Similarity	NPC35000
0.9032	High Similarity	NPC46551
0.9	High Similarity	NPC117986
0.9	High Similarity	NPC188649
0.9	High Similarity	NPC211777
0.9	High Similarity	NPC207978
0.8987	High Similarity	NPC126723
0.8987	High Similarity	NPC263265
0.897	High Similarity	NPC236004
0.897	High Similarity	NPC471437
0.897	High Similarity	NPC94763
0.8963	High Similarity	NPC160818
0.8963	High Similarity	NPC169299
0.8957	High Similarity	NPC296558
0.8951	High Similarity	NPC121995
0.8951	High Similarity	NPC97574
0.8951	High Similarity	NPC93172
0.8944	High Similarity	NPC419
0.8944	High Similarity	NPC469846
0.8938	High Similarity	NPC191828
0.8938	High Similarity	NPC287559
0.8931	High Similarity	NPC472778
0.8931	High Similarity	NPC472776
0.8931	High Similarity	NPC472777
0.8924	High Similarity	NPC92979
0.891	High Similarity	NPC476122
0.8896	High Similarity	NPC262198
0.8882	High Similarity	NPC18986
0.8882	High Similarity	NPC68848
0.8875	High Similarity	NPC262872
0.8862	High Similarity	NPC472665
0.8854	High Similarity	NPC18135
0.8848	High Similarity	NPC285227
0.8846	High Similarity	NPC125182
0.8846	High Similarity	NPC69647
0.8841	High Similarity	NPC472766
0.8841	High Similarity	NPC472765
0.8839	High Similarity	NPC255414
0.8834	High Similarity	NPC478178
0.8834	High Similarity	NPC149945
0.8834	High Similarity	NPC472141
0.8827	High Similarity	NPC472139
0.882	High Similarity	NPC470789
0.8812	High Similarity	NPC470118
0.8812	High Similarity	NPC88007
0.8812	High Similarity	NPC197137
0.8802	High Similarity	NPC262386
0.8797	High Similarity	NPC75906
0.8797	High Similarity	NPC33938
0.8788	High Similarity	NPC470995
0.878	High Similarity	NPC270312
0.878	High Similarity	NPC472764
0.878	High Similarity	NPC100333
0.8774	High Similarity	NPC346
0.8766	High Similarity	NPC137295
0.8766	High Similarity	NPC142113
0.8766	High Similarity	NPC476944
0.8758	High Similarity	NPC473368
0.8743	High Similarity	NPC469576
0.8743	High Similarity	NPC471632
0.8742	High Similarity	NPC57998
0.8734	High Similarity	NPC272590
0.8718	High Similarity	NPC470941
0.8718	High Similarity	NPC250228
0.8713	High Similarity	NPC247563
0.8713	High Similarity	NPC242068
0.8712	High Similarity	NPC165218
0.8712	High Similarity	NPC285567
0.8701	High Similarity	NPC476946
0.8696	High Similarity	NPC194499
0.8696	High Similarity	NPC195954
0.869	High Similarity	NPC469633
0.8688	High Similarity	NPC141538
0.8688	High Similarity	NPC296807
0.8688	High Similarity	NPC155939
0.8679	High Similarity	NPC268905
0.8675	High Similarity	NPC302392
0.8671	High Similarity	NPC470997
0.8667	High Similarity	NPC476224
0.8667	High Similarity	NPC478179
0.8659	High Similarity	NPC56358
0.8659	High Similarity	NPC146991
0.865	High Similarity	NPC472767
0.865	High Similarity	NPC470792
0.865	High Similarity	NPC197596
0.8647	High Similarity	NPC470938
0.8642	High Similarity	NPC475226
0.8642	High Similarity	NPC474611
0.8636	High Similarity	NPC121158
0.8634	High Similarity	NPC41880
0.8627	High Similarity	NPC90296
0.8623	High Similarity	NPC159232
0.8616	High Similarity	NPC116717
0.8614	High Similarity	NPC327922
0.8608	High Similarity	NPC472654
0.8608	High Similarity	NPC470998
0.8608	High Similarity	NPC234494
0.8608	High Similarity	NPC195325
0.8605	High Similarity	NPC105395
0.8599	High Similarity	NPC221809

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 NPC470940 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	308
0.1-0.2	1004
0.2-0.3	2140
0.3-0.4	2607
0.4-0.5	1836
0.5-0.6	911
0.6-0.7	281
0.7-0.8	59
0.8-0.85	4
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8765	High Similarity	NPD8434	Phase 2
0.8457	Intermediate Similarity	NPD5760	Phase 2
0.8457	Intermediate Similarity	NPD5761	Phase 2
0.8253	Intermediate Similarity	NPD5537	Clinical (unspecified phase)
0.7841	Intermediate Similarity	NPD6764	Approved
0.7841	Intermediate Similarity	NPD6765	Approved
0.7765	Intermediate Similarity	NPD7075	Discontinued
0.7692	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7667	Intermediate Similarity	NPD6785	Approved
0.7667	Intermediate Similarity	NPD6784	Approved
0.7569	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7542	Intermediate Similarity	NPD6559	Discontinued
0.7515	Intermediate Similarity	NPD6599	Discontinued
0.7513	Intermediate Similarity	NPD8404	Phase 2
0.75	Intermediate Similarity	NPD4628	Phase 3
0.7485	Intermediate Similarity	NPD7819	Suspended
0.7471	Intermediate Similarity	NPD7411	Suspended
0.7459	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7442	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7432	Intermediate Similarity	NPD8150	Discontinued
0.7427	Intermediate Similarity	NPD6801	Discontinued
0.7399	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7371	Intermediate Similarity	NPD5494	Approved
0.7356	Intermediate Similarity	NPD3749	Approved
0.7353	Intermediate Similarity	NPD3226	Approved
0.7341	Intermediate Similarity	NPD3817	Phase 2
0.7341	Intermediate Similarity	NPD5402	Approved
0.731	Intermediate Similarity	NPD4380	Phase 2
0.7303	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7303	Intermediate Similarity	NPD6166	Phase 2
0.7303	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7299	Intermediate Similarity	NPD3882	Suspended
0.7283	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7278	Intermediate Similarity	NPD5844	Phase 1
0.7278	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7268	Intermediate Similarity	NPD8312	Approved
0.7268	Intermediate Similarity	NPD8313	Approved
0.7263	Intermediate Similarity	NPD7473	Discontinued
0.7262	Intermediate Similarity	NPD6799	Approved
0.7257	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7235	Intermediate Similarity	NPD5403	Approved
0.7232	Intermediate Similarity	NPD1247	Approved
0.7229	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7225	Intermediate Similarity	NPD1934	Approved
0.7222	Intermediate Similarity	NPD3751	Discontinued
0.7222	Intermediate Similarity	NPD3818	Discontinued
0.7219	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7216	Intermediate Similarity	NPD919	Approved
0.7213	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7212	Intermediate Similarity	NPD1471	Phase 3
0.7207	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7198	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7186	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7158	Intermediate Similarity	NPD7251	Discontinued
0.7143	Intermediate Similarity	NPD7074	Phase 3
0.7135	Intermediate Similarity	NPD920	Approved
0.7135	Intermediate Similarity	NPD8127	Discontinued
0.7127	Intermediate Similarity	NPD7799	Discontinued
0.712	Intermediate Similarity	NPD7808	Phase 3
0.7118	Intermediate Similarity	NPD5401	Approved
0.7118	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7108	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7104	Intermediate Similarity	NPD6797	Phase 2
0.7101	Intermediate Similarity	NPD7236	Approved
0.7095	Intermediate Similarity	NPD6232	Discontinued
0.7088	Intermediate Similarity	NPD7054	Approved
0.7077	Intermediate Similarity	NPD7435	Discontinued
0.7074	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7052	Intermediate Similarity	NPD7458	Discontinued
0.7049	Intermediate Similarity	NPD7472	Approved
0.7043	Intermediate Similarity	NPD8407	Phase 2
0.7039	Intermediate Similarity	NPD6959	Discontinued
0.7024	Intermediate Similarity	NPD7907	Approved
0.7018	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7018	Intermediate Similarity	NPD2532	Approved
0.7018	Intermediate Similarity	NPD2534	Approved
0.7018	Intermediate Similarity	NPD2533	Approved
0.7006	Intermediate Similarity	NPD2346	Discontinued
0.7	Intermediate Similarity	NPD3787	Discontinued
0.6994	Remote Similarity	NPD7239	Suspended
0.6989	Remote Similarity	NPD2801	Approved
0.6989	Remote Similarity	NPD1465	Phase 2
0.6982	Remote Similarity	NPD3750	Approved
0.6977	Remote Similarity	NPD6273	Approved
0.6973	Remote Similarity	NPD7685	Pre-registration
0.6973	Remote Similarity	NPD8368	Discontinued
0.6964	Remote Similarity	NPD1549	Phase 2
0.6961	Remote Similarity	NPD3926	Phase 2
0.6957	Remote Similarity	NPD5619	Clinical (unspecified phase)
0.6954	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6946	Remote Similarity	NPD6099	Approved
0.6946	Remote Similarity	NPD6100	Approved
0.694	Remote Similarity	NPD7893	Clinical (unspecified phase)
0.694	Remote Similarity	NPD7228	Approved
0.6932	Remote Similarity	NPD37	Approved
0.6927	Remote Similarity	NPD4111	Phase 1
0.6927	Remote Similarity	NPD4665	Approved
0.6927	Remote Similarity	NPD6234	Discontinued
0.6923	Remote Similarity	NPD6777	Approved
0.6923	Remote Similarity	NPD6779	Approved
0.6923	Remote Similarity	NPD6776	Approved
0.6923	Remote Similarity	NPD6781	Approved
0.6923	Remote Similarity	NPD6778	Approved
0.6923	Remote Similarity	NPD2800	Approved
0.6923	Remote Similarity	NPD6782	Approved
0.6923	Remote Similarity	NPD6780	Approved
0.6919	Remote Similarity	NPD7410	Clinical (unspecified phase)
0.691	Remote Similarity	NPD7768	Phase 2
0.691	Remote Similarity	NPD4965	Approved
0.691	Remote Similarity	NPD4967	Phase 2
0.691	Remote Similarity	NPD4966	Approved
0.6909	Remote Similarity	NPD6355	Discontinued
0.6905	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.6905	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6901	Remote Similarity	NPD643	Clinical (unspecified phase)
0.6895	Remote Similarity	NPD8360	Approved
0.6895	Remote Similarity	NPD8361	Approved
0.6886	Remote Similarity	NPD2799	Discontinued
0.6879	Remote Similarity	NPD1512	Approved
0.6868	Remote Similarity	NPD7184	Clinical (unspecified phase)
0.6866	Remote Similarity	NPD7875	Clinical (unspecified phase)
0.6866	Remote Similarity	NPD7874	Approved
0.6853	Remote Similarity	NPD3057	Approved
0.6845	Remote Similarity	NPD2796	Approved
0.6845	Remote Similarity	NPD1551	Phase 2
0.6837	Remote Similarity	NPD4107	Approved
0.6829	Remote Similarity	NPD3268	Approved
0.6818	Remote Similarity	NPD7696	Phase 3
0.6818	Remote Similarity	NPD7697	Approved
0.6818	Remote Similarity	NPD7698	Approved
0.6806	Remote Similarity	NPD8435	Approved
0.6805	Remote Similarity	NPD2344	Approved
0.6786	Remote Similarity	NPD3748	Approved
0.6786	Remote Similarity	NPD8285	Discontinued
0.6786	Remote Similarity	NPD7033	Discontinued
0.6784	Remote Similarity	NPD8166	Discontinued
0.6784	Remote Similarity	NPD7871	Phase 2
0.6784	Remote Similarity	NPD7870	Phase 2
0.6784	Remote Similarity	NPD8320	Phase 1
0.6784	Remote Similarity	NPD8319	Approved
0.6768	Remote Similarity	NPD2972	Approved
0.6768	Remote Similarity	NPD3533	Approved
0.6766	Remote Similarity	NPD7701	Phase 2
0.6765	Remote Similarity	NPD970	Clinical (unspecified phase)
0.6763	Remote Similarity	NPD1511	Approved
0.6758	Remote Similarity	NPD7199	Phase 2
0.6749	Remote Similarity	NPD7801	Approved
0.6747	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.6746	Remote Similarity	NPD2935	Discontinued
0.6744	Remote Similarity	NPD6190	Approved
0.6743	Remote Similarity	NPD6980	Clinical (unspecified phase)
0.6739	Remote Similarity	NPD2403	Approved
0.6734	Remote Similarity	NPD7497	Discontinued
0.6727	Remote Similarity	NPD2313	Discontinued
0.6726	Remote Similarity	NPD7097	Phase 1
0.6725	Remote Similarity	NPD1243	Approved
0.672	Remote Similarity	NPD8470	Clinical (unspecified phase)
0.6717	Remote Similarity	NPD4482	Phase 3
0.6707	Remote Similarity	NPD6832	Phase 2
0.6707	Remote Similarity	NPD447	Suspended
0.6706	Remote Similarity	NPD5762	Approved
0.6706	Remote Similarity	NPD5763	Approved
0.6704	Remote Similarity	NPD8455	Phase 2
0.6702	Remote Similarity	NPD8424	Clinical (unspecified phase)
0.6702	Remote Similarity	NPD7240	Approved
0.6686	Remote Similarity	NPD1510	Phase 2
0.6686	Remote Similarity	NPD7003	Approved
0.6684	Remote Similarity	NPD8485	Approved
0.6684	Remote Similarity	NPD8090	Clinical (unspecified phase)
0.6683	Remote Similarity	NPD2491	Approved
0.6667	Remote Similarity	NPD7783	Phase 2
0.6667	Remote Similarity	NPD7782	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD7095	Approved
0.6667	Remote Similarity	NPD6535	Approved
0.6667	Remote Similarity	NPD6534	Approved
0.6667	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.665	Remote Similarity	NPD8151	Discontinued
0.665	Remote Similarity	NPD7700	Phase 2
0.665	Remote Similarity	NPD7699	Phase 2
0.6647	Remote Similarity	NPD2309	Approved
0.663	Remote Similarity	NPD7229	Phase 3
0.663	Remote Similarity	NPD7058	Phase 2
0.663	Remote Similarity	NPD5710	Approved
0.663	Remote Similarity	NPD7057	Phase 3
0.663	Remote Similarity	NPD5711	Approved
0.663	Remote Similarity	NPD6808	Phase 2
0.6627	Remote Similarity	NPD3764	Approved
0.6627	Remote Similarity	NPD6798	Discontinued
0.6627	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6606	Remote Similarity	NPD7048	Phase 3
0.66	Remote Similarity	NPD6823	Phase 2
0.66	Remote Similarity	NPD3448	Approved
0.659	Remote Similarity	NPD4110	Phase 3
0.659	Remote Similarity	NPD4109	Clinical (unspecified phase)
0.6588	Remote Similarity	NPD4308	Phase 3
0.6587	Remote Similarity	NPD6233	Phase 2
0.6585	Remote Similarity	NPD5676	Approved
0.6583	Remote Similarity	NPD7501	Clinical (unspecified phase)
0.6583	Remote Similarity	NPD8486	Clinical (unspecified phase)
0.6568	Remote Similarity	NPD1607	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