NPASS Compound

Structure

CID154962 OpenBabel06191715522D 29 34 0 0 1 0 0 0 0 0999 V2000 2.5665 0.9664 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5937 -2.9919 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3947 -2.0472 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3760 -3.6095 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0296 -2.9496 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2773 -2.0778 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5660 0.0001 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.7584 -2.3919 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.7883 -2.3914 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.0826 -1.4853 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.2307 -2.0349 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.3468 -0.5677 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0114 -1.4668 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0058 -1.0160 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7468 -0.5495 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.6760 -2.6919 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4904 -1.4731 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -0.4492 -1.4680 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 1.7847 -0.5670 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.7883 -0.5575 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -1.2315 -3.0012 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.2660 -0.2696 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.9306 -1.7647 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.6795 -0.0497 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.4880 0.3476 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.0481 -1.4858 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0058 -1.9329 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7123 -0.5487 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 7 1 0 0 0 0 2 16 1 0 0 0 0 3 16 1 0 0 0 0 4 16 1 0 0 0 0 5 8 1 0 0 0 0 5 9 1 0 0 0 0 6 10 1 0 0 0 0 6 17 1 0 0 0 0 7 12 1 0 0 0 0 7 19 1 6 0 0 0 8 16 1 0 0 0 0 8 18 1 1 0 0 0 9 17 1 1 0 0 0 9 27 1 0 0 0 0 10 19 1 6 0 0 0 10 26 1 0 0 0 0 11 13 1 0 0 0 0 11 18 1 1 0 0 0 11 21 1 0 0 0 0 12 22 2 0 0 0 0 12 26 1 0 0 0 0 13 23 2 0 0 0 0 13 28 1 0 0 0 0 14 20 1 0 0 0 0 14 24 2 0 0 0 0 14 27 1 0 0 0 0 15 18 1 6 0 0 0 15 28 1 0 0 0 0 15 29 1 0 0 0 0 17 18 1 0 0 0 0 17 20 1 0 0 0 0 19 20 1 1 0 0 0 19 25 1 0 0 0 0 20 29 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	408.14
Volume:	374.34
LogP:	1.882
LogD:	0.782
LogS:	-4.164
# Rotatable Bonds:	1
TPSA:	128.59
# H-Bond Aceptor:	9
# H-Bond Donor:	2
# Rings:	6
# Heavy Atoms:	9

MedChem Properties

QED Drug-Likeness Score:	0.517
Synthetic Accessibility Score:	6.43
Fsp3:	0.85
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.353
MDCK Permeability:	5.372270243242383e-05
Pgp-inhibitor:	0.969
Pgp-substrate:	0.83
Human Intestinal Absorption (HIA):	0.008
20% Bioavailability (F20%):	0.026
30% Bioavailability (F30%):	0.308

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.533
Plasma Protein Binding (PPB):	45.10321807861328%
Volume Distribution (VD):	1.046
Pgp-substrate:	64.46022033691406%

ADMET: Metabolism

CYP1A2-inhibitor:	0.008
CYP1A2-substrate:	0.825
CYP2C19-inhibitor:	0.021
CYP2C19-substrate:	0.743
CYP2C9-inhibitor:	0.008
CYP2C9-substrate:	0.027
CYP2D6-inhibitor:	0.01
CYP2D6-substrate:	0.166
CYP3A4-inhibitor:	0.041
CYP3A4-substrate:	0.388

ADMET: Excretion

Clearance (CL):	2.221
Half-life (T1/2):	0.25

ADMET: Toxicity

hERG Blockers:	0.006
Human Hepatotoxicity (H-HT):	0.093
Drug-inuced Liver Injury (DILI):	0.81
AMES Toxicity:	0.883
Rat Oral Acute Toxicity:	0.994
Maximum Recommended Daily Dose:	0.948
Skin Sensitization:	0.078
Carcinogencity:	0.931
Eye Corrosion:	0.003
Eye Irritation:	0.028
Respiratory Toxicity:	0.972

Download Data

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

Natural Product: NPC154962

Natural Product ID:	NPC154962
*Common Name:**	FPUXKXIZEIDQKW-QOHNDBQUSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	FPUXKXIZEIDQKW-QOHNDBQUSA-N
Standard InCHI:	InChI=1S/C20H24O9/c1-7-12(22)26-10-6-17-9-5-8(16(2,3)4)18(17)11(21)13(23)28-15(18)29-20(17,14(24)27-9)19(7,10)25/h7-11,15,21,25H,5-6H2,1-4H3/t7-,8+,9-,10-,11+,15-,17?,18?,19-,20?/m1/s1
SMILES:	O=C1O[C@H]2[C@@]([C@@H]1C)(O)C13C4(C2)[C@H](OC3=O)C[C@H](C24[C@@H](O1)OC(=O)[C@@H]2O)C(C)(C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1472160
PubChem CID:	15944765
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001283] Terpene lactones [CHEMONTID:0001538] Diterpene lactones [CHEMONTID:0001768] Ginkgolides and bilobalides

*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
NPO26293	Ginkgo biloba	Species	Ginkgoaceae	Eukaryota	n.a.	leaf	n.a.	DOI[10.1016/S0031-9422(01)00320-X]
NPO26293	Ginkgo biloba	Species	Ginkgoaceae	Eukaryota	n.a.	leaf	n.a.	PMID[11738417]
NPO26293	Ginkgo biloba	Species	Ginkgoaceae	Eukaryota	n.a.	fruit	n.a.	PMID[21462031]
NPO26293	Ginkgo biloba	Species	Ginkgoaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO26293	Ginkgo biloba	Species	Ginkgoaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO26293	Ginkgo biloba	Species	Ginkgoaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO26293	Ginkgo biloba	Species	Ginkgoaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO26293	Ginkgo biloba	Species	Ginkgoaceae	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
Potency	4

Activity Type	# Activity
Individual Protein	4

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT3	Individual Protein	Thioredoxin glutathione reductase	Schistosoma mansoni	Potency	=	25118.9	nM	PMID[485637]
NPT444	Individual Protein	Ubiquitin carboxyl-terminal hydrolase 1	Homo sapiens	Potency	n.a.	251.2	nM	PMID[485637]
NPT535	Individual Protein	Parathyroid hormone receptor	Homo sapiens	Potency	n.a.	125892.5	nM	PMID[485637]
NPT93	Individual Protein	Survival motor neuron protein	Homo sapiens	Potency	=	3548.1	nM	PMID[485637]

☑ 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 NPC154962 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	818
0.1-0.2	5698
0.2-0.3	13689
0.3-0.4	11709
0.4-0.5	7337
0.5-0.6	3039
0.6-0.7	345
0.7-0.8	33
0.8-0.85	9
0.85-0.9	7
0.9-0.95	2
0.95-1	11

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC132304
1.0	High Similarity	NPC88890
1.0	High Similarity	NPC177518
1.0	High Similarity	NPC114365
1.0	High Similarity	NPC18433
1.0	High Similarity	NPC169089
1.0	High Similarity	NPC18044
1.0	High Similarity	NPC123070
0.9792	High Similarity	NPC292803
0.9175	High Similarity	NPC278028
0.9175	High Similarity	NPC328180
0.8762	High Similarity	NPC182185
0.875	High Similarity	NPC220773
0.875	High Similarity	NPC278693
0.8738	High Similarity	NPC168890
0.8667	High Similarity	NPC217041
0.8598	High Similarity	NPC98870
0.8571	High Similarity	NPC167044
0.8558	High Similarity	NPC41674
0.8558	High Similarity	NPC469441
0.8558	High Similarity	NPC228311
0.8476	Intermediate Similarity	NPC469788
0.8476	Intermediate Similarity	NPC176756
0.8476	Intermediate Similarity	NPC469787
0.8476	Intermediate Similarity	NPC290247
0.8396	Intermediate Similarity	NPC329876
0.8021	Intermediate Similarity	NPC157328
0.8	Intermediate Similarity	NPC162024
0.7981	Intermediate Similarity	NPC274695
0.785	Intermediate Similarity	NPC469350
0.7778	Intermediate Similarity	NPC473701
0.7778	Intermediate Similarity	NPC473526
0.7745	Intermediate Similarity	NPC474699
0.77	Intermediate Similarity	NPC31349
0.7692	Intermediate Similarity	NPC470191
0.7632	Intermediate Similarity	NPC470116
0.7632	Intermediate Similarity	NPC470115
0.7624	Intermediate Similarity	NPC470009
0.76	Intermediate Similarity	NPC470657
0.7565	Intermediate Similarity	NPC475490
0.7545	Intermediate Similarity	NPC166079
0.7477	Intermediate Similarity	NPC211087
0.7455	Intermediate Similarity	NPC100078
0.7431	Intermediate Similarity	NPC213528
0.7431	Intermediate Similarity	NPC244969
0.7414	Intermediate Similarity	NPC277583
0.7387	Intermediate Similarity	NPC306776
0.736	Intermediate Similarity	NPC224623
0.7353	Intermediate Similarity	NPC314364
0.735	Intermediate Similarity	NPC179429
0.7339	Intermediate Similarity	NPC469351
0.7333	Intermediate Similarity	NPC472238
0.7333	Intermediate Similarity	NPC472237
0.7328	Intermediate Similarity	NPC79193
0.7297	Intermediate Similarity	NPC88469
0.7258	Intermediate Similarity	NPC13071
0.7238	Intermediate Similarity	NPC474065
0.7217	Intermediate Similarity	NPC473062
0.72	Intermediate Similarity	NPC212340
0.7182	Intermediate Similarity	NPC478181
0.7177	Intermediate Similarity	NPC172823
0.7165	Intermediate Similarity	NPC470117
0.7165	Intermediate Similarity	NPC475376
0.7156	Intermediate Similarity	NPC253995
0.7131	Intermediate Similarity	NPC186339
0.7115	Intermediate Similarity	NPC33398
0.7109	Intermediate Similarity	NPC256618
0.7109	Intermediate Similarity	NPC219058
0.7097	Intermediate Similarity	NPC11732
0.7083	Intermediate Similarity	NPC125164
0.7073	Intermediate Similarity	NPC144625
0.7059	Intermediate Similarity	NPC473791
0.7041	Intermediate Similarity	NPC70996
0.7041	Intermediate Similarity	NPC83108
0.7041	Intermediate Similarity	NPC214030
0.7037	Intermediate Similarity	NPC215570
0.7027	Intermediate Similarity	NPC259654
0.7027	Intermediate Similarity	NPC298266
0.7027	Intermediate Similarity	NPC178853
0.7019	Intermediate Similarity	NPC51662
0.7018	Intermediate Similarity	NPC203974
0.6992	Remote Similarity	NPC1538
0.699	Remote Similarity	NPC478111
0.6983	Remote Similarity	NPC475463
0.6923	Remote Similarity	NPC469824
0.6911	Remote Similarity	NPC192309
0.6909	Remote Similarity	NPC470632
0.6909	Remote Similarity	NPC74466
0.6909	Remote Similarity	NPC58267
0.6909	Remote Similarity	NPC261372
0.6909	Remote Similarity	NPC263674
0.6903	Remote Similarity	NPC471253
0.6897	Remote Similarity	NPC236753
0.6897	Remote Similarity	NPC228190
0.6881	Remote Similarity	NPC21897
0.6875	Remote Similarity	NPC42206
0.6855	Remote Similarity	NPC42747
0.6847	Remote Similarity	NPC292775
0.6842	Remote Similarity	NPC470167
0.6838	Remote Similarity	NPC106760
0.6837	Remote Similarity	NPC228411
0.6825	Remote Similarity	NPC2757
0.6818	Remote Similarity	NPC116683
0.6818	Remote Similarity	NPC193785
0.6818	Remote Similarity	NPC475765
0.6818	Remote Similarity	NPC475785
0.6818	Remote Similarity	NPC476728
0.6814	Remote Similarity	NPC470172
0.681	Remote Similarity	NPC117604
0.681	Remote Similarity	NPC110701
0.6807	Remote Similarity	NPC97002
0.6807	Remote Similarity	NPC285086
0.68	Remote Similarity	NPC475616
0.6796	Remote Similarity	NPC474266
0.6789	Remote Similarity	NPC206878
0.6783	Remote Similarity	NPC215408
0.6783	Remote Similarity	NPC127235
0.6759	Remote Similarity	NPC469627
0.6757	Remote Similarity	NPC471241
0.6757	Remote Similarity	NPC472273
0.6754	Remote Similarity	NPC107385
0.6754	Remote Similarity	NPC329704
0.6754	Remote Similarity	NPC473406
0.6752	Remote Similarity	NPC227879
0.6752	Remote Similarity	NPC208333
0.6746	Remote Similarity	NPC273962
0.6741	Remote Similarity	NPC471171
0.6735	Remote Similarity	NPC477867
0.6731	Remote Similarity	NPC291310
0.6726	Remote Similarity	NPC471767
0.6726	Remote Similarity	NPC67296
0.6726	Remote Similarity	NPC216911
0.6724	Remote Similarity	NPC197813
0.6724	Remote Similarity	NPC80338
0.6724	Remote Similarity	NPC148270
0.6699	Remote Similarity	NPC475849
0.6698	Remote Similarity	NPC475773
0.6697	Remote Similarity	NPC475788
0.6697	Remote Similarity	NPC35164
0.6695	Remote Similarity	NPC193741
0.6695	Remote Similarity	NPC98633
0.6667	Remote Similarity	NPC471254
0.6667	Remote Similarity	NPC474297
0.6667	Remote Similarity	NPC250594
0.6667	Remote Similarity	NPC49393
0.6667	Remote Similarity	NPC475319
0.6667	Remote Similarity	NPC145553
0.6667	Remote Similarity	NPC102619
0.6667	Remote Similarity	NPC65359
0.6667	Remote Similarity	NPC224414
0.6667	Remote Similarity	NPC469826
0.6667	Remote Similarity	NPC179922
0.6667	Remote Similarity	NPC319570
0.6667	Remote Similarity	NPC472079
0.6667	Remote Similarity	NPC92890
0.6667	Remote Similarity	NPC202898
0.6642	Remote Similarity	NPC194854
0.6642	Remote Similarity	NPC48813
0.6639	Remote Similarity	NPC474750
0.6639	Remote Similarity	NPC472003
0.6638	Remote Similarity	NPC474101
0.6638	Remote Similarity	NPC170432
0.6638	Remote Similarity	NPC44004
0.6637	Remote Similarity	NPC476211
0.6637	Remote Similarity	NPC476320
0.6636	Remote Similarity	NPC221993
0.6636	Remote Similarity	NPC217567
0.6636	Remote Similarity	NPC76136
0.6636	Remote Similarity	NPC329713
0.6636	Remote Similarity	NPC470424
0.6633	Remote Similarity	NPC248427
0.6614	Remote Similarity	NPC104427
0.6612	Remote Similarity	NPC300051
0.661	Remote Similarity	NPC273002
0.661	Remote Similarity	NPC94086
0.661	Remote Similarity	NPC233433
0.661	Remote Similarity	NPC473817
0.661	Remote Similarity	NPC92297
0.661	Remote Similarity	NPC220836
0.6609	Remote Similarity	NPC37240
0.6609	Remote Similarity	NPC329834
0.6609	Remote Similarity	NPC473148
0.6607	Remote Similarity	NPC304445
0.6607	Remote Similarity	NPC471150
0.6607	Remote Similarity	NPC236580
0.6606	Remote Similarity	NPC475878
0.6606	Remote Similarity	NPC235051
0.6602	Remote Similarity	NPC216941
0.66	Remote Similarity	NPC279575
0.6594	Remote Similarity	NPC475462
0.6594	Remote Similarity	NPC16729
0.6585	Remote Similarity	NPC475401
0.6583	Remote Similarity	NPC475851
0.6583	Remote Similarity	NPC475924
0.6583	Remote Similarity	NPC477489
0.6579	Remote Similarity	NPC3488
0.6579	Remote Similarity	NPC304624
0.6579	Remote Similarity	NPC476230
0.6579	Remote Similarity	NPC474053
0.6579	Remote Similarity	NPC287539

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 NPC154962 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	1104
0.1-0.2	4642
0.2-0.3	2279
0.3-0.4	698
0.4-0.5	325
0.5-0.6	90
0.6-0.7	10
0.7-0.8	0
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	2

Similarity Score	Similarity Level	Drug ID	Developmental Stage
1.0	High Similarity	NPD4057	Clinical (unspecified phase)
1.0	High Similarity	NPD4056	Clinical (unspecified phase)
0.7339	Intermediate Similarity	NPD1700	Approved
0.6696	Remote Similarity	NPD8170	Clinical (unspecified phase)
0.6562	Remote Similarity	NPD8293	Discontinued
0.6562	Remote Similarity	NPD7078	Approved
0.6512	Remote Similarity	NPD7736	Approved
0.6508	Remote Similarity	NPD6370	Approved
0.6406	Remote Similarity	NPD7492	Approved
0.6357	Remote Similarity	NPD6616	Approved
0.6349	Remote Similarity	NPD6059	Approved
0.6349	Remote Similarity	NPD6054	Approved
0.6299	Remote Similarity	NPD6015	Approved
0.6299	Remote Similarity	NPD6016	Approved
0.625	Remote Similarity	NPD5988	Approved
0.622	Remote Similarity	NPD6319	Approved
0.6154	Remote Similarity	NPD4802	Phase 2
0.6154	Remote Similarity	NPD4238	Approved
0.6122	Remote Similarity	NPD898	Approved
0.6122	Remote Similarity	NPD896	Approved
0.6122	Remote Similarity	NPD897	Approved
0.6111	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6102	Remote Similarity	NPD8085	Approved
0.6102	Remote Similarity	NPD8082	Approved
0.6102	Remote Similarity	NPD8138	Approved
0.6102	Remote Similarity	NPD8086	Approved
0.6102	Remote Similarity	NPD8083	Approved
0.6102	Remote Similarity	NPD8084	Approved
0.6102	Remote Similarity	NPD8139	Approved
0.609	Remote Similarity	NPD7319	Approved
0.605	Remote Similarity	NPD8275	Approved
0.605	Remote Similarity	NPD8276	Approved
0.6033	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6	Remote Similarity	NPD8081	Approved
0.5985	Remote Similarity	NPD7507	Approved
0.5965	Remote Similarity	NPD8171	Discontinued
0.595	Remote Similarity	NPD8393	Approved
0.5943	Remote Similarity	NPD7329	Approved
0.59	Remote Similarity	NPD229	Approved
0.5896	Remote Similarity	NPD6033	Approved
0.5873	Remote Similarity	NPD8133	Approved
0.5859	Remote Similarity	NPD6009	Approved
0.5833	Remote Similarity	NPD8328	Phase 3
0.5794	Remote Similarity	NPD6882	Approved
0.5772	Remote Similarity	NPD8140	Approved
0.5772	Remote Similarity	NPD8307	Discontinued
0.5772	Remote Similarity	NPD6412	Phase 2
0.5726	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.5726	Remote Similarity	NPD7320	Approved
0.5714	Remote Similarity	NPD8961	Approved
0.5714	Remote Similarity	NPD3702	Approved
0.5702	Remote Similarity	NPD8301	Approved
0.5702	Remote Similarity	NPD8300	Approved
0.5693	Remote Similarity	NPD5956	Approved
0.5682	Remote Similarity	NPD8274	Clinical (unspecified phase)
0.568	Remote Similarity	NPD8306	Approved
0.568	Remote Similarity	NPD6373	Approved
0.568	Remote Similarity	NPD8305	Approved
0.568	Remote Similarity	NPD6372	Approved
0.5673	Remote Similarity	NPD3181	Approved
0.5669	Remote Similarity	NPD8297	Approved
0.5657	Remote Similarity	NPD7909	Approved
0.5639	Remote Similarity	NPD8080	Discontinued
0.5636	Remote Similarity	NPD6435	Approved
0.5635	Remote Similarity	NPD6371	Approved
0.5635	Remote Similarity	NPD8087	Discontinued
0.5625	Remote Similarity	NPD4632	Approved
0.56	Remote Similarity	NPD6686	Approved
0.56	Remote Similarity	NPD9496	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