NPASS Compound

Structure

NPC469787 OpenBabel07101718192D 42 49 0 0 1 0 0 0 0 0999 V2000 -2.0084 2.9313 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5481 2.4821 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6471 2.9160 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3238 0.9797 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8559 -0.2452 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0568 0.5991 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3351 1.7319 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8090 1.2580 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0469 2.4631 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3704 -0.6755 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7453 0.2364 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3013 2.2242 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.0509 2.3734 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.7379 1.7403 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.3865 -0.8541 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4062 1.5623 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.5000 1.5388 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.7699 1.2067 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.6394 2.3291 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5000 1.5388 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7186 0.7006 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.5229 0.8747 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7219 1.9188 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3351 1.7319 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.1840 0.4955 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8090 1.2580 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8090 0.5878 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.6037 0.7493 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.5047 0.3154 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8090 0.5878 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.5380 3.2319 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.9526 -1.7550 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.1854 3.2201 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.0878 2.3479 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.5178 0.7739 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.8786 -0.4567 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.4056 -0.1185 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.2670 1.3143 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.9126 0.0265 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.2910 0.4252 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.1957 1.0382 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 2 23 1 0 0 0 0 3 23 1 0 0 0 0 4 24 1 0 0 0 0 6 26 1 0 0 0 0 7 8 1 0 0 0 0 7 24 1 0 0 0 0 9 13 1 0 0 0 0 9 14 1 0 0 0 0 10 15 1 0 0 0 0 10 29 1 0 0 0 0 11 27 1 0 0 0 0 11 28 1 0 0 0 0 12 1 1 1 0 0 0 12 16 1 0 0 0 0 12 19 1 0 0 0 0 13 17 1 0 0 0 0 13 31 1 1 0 0 0 14 23 1 0 0 0 0 14 28 1 1 0 0 0 15 32 2 0 0 0 0 15 39 1 0 0 0 0 16 18 1 0 0 0 0 16 26 1 1 0 0 0 17 20 1 0 0 0 0 17 27 1 6 0 0 0 18 21 1 0 0 0 0 18 38 1 6 0 0 0 19 24 1 0 0 0 0 19 33 2 0 0 0 0 20 34 2 0 0 0 0 21 25 1 6 0 0 0 21 40 1 0 0 0 0 22 25 1 0 0 0 0 22 35 2 0 0 0 0 22 38 1 0 0 0 0 23 41 1 0 0 0 0 24 26 1 1 0 0 0 25 5 1 6 0 0 0 25 36 1 0 0 0 0 26 30 1 1 0 0 0 27 8 1 1 0 0 0 27 42 1 0 0 0 0 28 29 1 1 0 0 0 28 39 1 0 0 0 0 29 37 1 1 0 0 0 29 41 1 0 0 0 0 30 20 1 6 0 0 0 30 40 1 0 0 0 0 30 42 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	590.24
Volume:	553.921
LogP:	1.914
LogD:	1.131
LogS:	-4.208
# Rotatable Bonds:	0
TPSA:	175.12
# H-Bond Aceptor:	12
# H-Bond Donor:	3
# Rings:	8
# Heavy Atoms:	12

MedChem Properties

QED Drug-Likeness Score:	0.33
Synthetic Accessibility Score:	7.813
Fsp3:	0.867
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:	-5.447
MDCK Permeability:	5.996118125040084e-05
Pgp-inhibitor:	0.96
Pgp-substrate:	0.99
Human Intestinal Absorption (HIA):	0.772
20% Bioavailability (F20%):	0.998
30% Bioavailability (F30%):	0.995

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.428
Plasma Protein Binding (PPB):	43.35068130493164%
Volume Distribution (VD):	0.507
Pgp-substrate:	47.89554977416992%

ADMET: Metabolism

CYP1A2-inhibitor:	0.002
CYP1A2-substrate:	0.991
CYP2C19-inhibitor:	0.008
CYP2C19-substrate:	0.608
CYP2C9-inhibitor:	0.003
CYP2C9-substrate:	0.001
CYP2D6-inhibitor:	0.001
CYP2D6-substrate:	0.026
CYP3A4-inhibitor:	0.855
CYP3A4-substrate:	0.853

ADMET: Excretion

Clearance (CL):	8.188
Half-life (T1/2):	0.201

ADMET: Toxicity

hERG Blockers:	0.013
Human Hepatotoxicity (H-HT):	0.088
Drug-inuced Liver Injury (DILI):	0.821
AMES Toxicity:	0.69
Rat Oral Acute Toxicity:	0.995
Maximum Recommended Daily Dose:	0.714
Skin Sensitization:	0.137
Carcinogencity:	0.968
Eye Corrosion:	0.003
Eye Irritation:	0.012
Respiratory Toxicity:	0.981

Download Data

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

Natural Product: NPC469787

Natural Product ID:	NPC469787
*Common Name:**	Arisanlactone B
IUPAC Name:	n.a.
Synonyms:	Arisanlactone B
Standard InCHIKey:	AZJCWYJWWDUDMB-VZYFBGLHSA-N
Standard InCHI:	InChI=1S/C30H38O12/c1-12-16-18-21(25(5,36)22(35)38-18)40-30-20(34)17-13(31)9-14-23(2,3)41-29(37)10-15(32)39-28(14,29)11-27(17,42-30)8-7-24(4,19(12)33)26(16,30)6/h12-14,16-18,21,31,36-37H,7-11H2,1-6H3/t12-,13+,14+,16-,17+,18-,21+,24-,25-,26+,27+,28-,29-,30-/m1/s1
SMILES:	O=C1O[C@]23[C@](C1)(O)OC([C@@H]3C[C@@H]([C@@H]1[C@@]3(C2)CC[C@]2([C@]4([C@](O3)(C1=O)O[C@H]1[C@@H]([C@H]4[C@H](C2=O)C)OC(=O)[C@]1(C)O)C)C)O)(C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1171809
PubChem CID:	49799343
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0003909] Fatty Acyls [CHEMONTID:0000513] Eicosanoids [CHEMONTID:0000514] Prostaglandins and related compounds

*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
NPO8584	Schisandra arisanensis	Species	Schisandraceae	Eukaryota	fruits	n.a.	n.a.	PMID[19673515]
NPO8584	Schisandra arisanensis	Species	Schisandraceae	Eukaryota	fruits	n.a.	n.a.	PMID[20536188]
NPO8584	Schisandra arisanensis	Species	Schisandraceae	Eukaryota	fruits	n.a.	n.a.	PMID[23265871]
NPO8584	Schisandra arisanensis	Species	Schisandraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO8584	Schisandra arisanensis	Species	Schisandraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO8584	Schisandra arisanensis	Species	Schisandraceae	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
Others	2

Activity Type	# Activity
Cell Line	1
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT2740	Cell Line	Neutrophils		Inhibition	=	22.24	%	PMID[520342]
NPT190	Organism	Human herpesvirus 1	Human herpesvirus 1	Inhibition	=	25.0	%	PMID[520342]

☑ 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 NPC469787 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	671
0.1-0.2	5292
0.2-0.3	12781
0.3-0.4	12377
0.4-0.5	7908
0.5-0.6	3312
0.6-0.7	292
0.7-0.8	30
0.8-0.85	15
0.85-0.9	3
0.9-0.95	8
0.95-1	8

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC469788
1.0	High Similarity	NPC290247
0.98	High Similarity	NPC217041
0.9703	High Similarity	NPC182185
0.9697	High Similarity	NPC41674
0.9697	High Similarity	NPC469441
0.9697	High Similarity	NPC228311
0.9515	High Similarity	NPC98870
0.9505	High Similarity	NPC329876
0.9406	High Similarity	NPC176756
0.9314	High Similarity	NPC167044
0.9314	High Similarity	NPC220773
0.9314	High Similarity	NPC278693
0.93	High Similarity	NPC469350
0.9118	High Similarity	NPC168890
0.91	High Similarity	NPC162024
0.89	High Similarity	NPC274695
0.8476	Intermediate Similarity	NPC18433
0.8476	Intermediate Similarity	NPC114365
0.8476	Intermediate Similarity	NPC88890
0.8476	Intermediate Similarity	NPC169089
0.8476	Intermediate Similarity	NPC177518
0.8476	Intermediate Similarity	NPC154962
0.8476	Intermediate Similarity	NPC18044
0.8476	Intermediate Similarity	NPC132304
0.8476	Intermediate Similarity	NPC123070
0.8348	Intermediate Similarity	NPC186339
0.8286	Intermediate Similarity	NPC292803
0.8136	Intermediate Similarity	NPC11732
0.8077	Intermediate Similarity	NPC278028
0.8077	Intermediate Similarity	NPC328180
0.7951	Intermediate Similarity	NPC224623
0.7934	Intermediate Similarity	NPC469351
0.7881	Intermediate Similarity	NPC1538
0.7798	Intermediate Similarity	NPC473526
0.7798	Intermediate Similarity	NPC473701
0.7797	Intermediate Similarity	NPC192309
0.7739	Intermediate Similarity	NPC475490
0.7723	Intermediate Similarity	NPC314364
0.7705	Intermediate Similarity	NPC13071
0.7647	Intermediate Similarity	NPC470009
0.7623	Intermediate Similarity	NPC172823
0.7583	Intermediate Similarity	NPC42747
0.7521	Intermediate Similarity	NPC144625
0.7479	Intermediate Similarity	NPC147635
0.7479	Intermediate Similarity	NPC163693
0.7426	Intermediate Similarity	NPC473791
0.7411	Intermediate Similarity	NPC166079
0.7379	Intermediate Similarity	NPC51662
0.7364	Intermediate Similarity	NPC478181
0.7339	Intermediate Similarity	NPC211087
0.7321	Intermediate Similarity	NPC100078
0.7304	Intermediate Similarity	NPC475463
0.7297	Intermediate Similarity	NPC244969
0.7297	Intermediate Similarity	NPC213528
0.7257	Intermediate Similarity	NPC306776
0.7248	Intermediate Similarity	NPC74466
0.7222	Intermediate Similarity	NPC470191
0.7203	Intermediate Similarity	NPC470115
0.7203	Intermediate Similarity	NPC470116
0.7196	Intermediate Similarity	NPC472238
0.7196	Intermediate Similarity	NPC472237
0.7157	Intermediate Similarity	NPC157328
0.7157	Intermediate Similarity	NPC474266
0.713	Intermediate Similarity	NPC76136
0.713	Intermediate Similarity	NPC329713
0.713	Intermediate Similarity	NPC217567
0.7115	Intermediate Similarity	NPC470657
0.7094	Intermediate Similarity	NPC473062
0.7091	Intermediate Similarity	NPC470632
0.7083	Intermediate Similarity	NPC179429
0.7059	Intermediate Similarity	NPC475849
0.7059	Intermediate Similarity	NPC79193
0.7054	Intermediate Similarity	NPC178853
0.7048	Intermediate Similarity	NPC31349
0.7043	Intermediate Similarity	NPC203974
0.7041	Intermediate Similarity	NPC179922
0.7027	Intermediate Similarity	NPC253995
0.7019	Intermediate Similarity	NPC478111
0.7018	Intermediate Similarity	NPC88469
0.7	Intermediate Similarity	NPC475616
0.6991	Remote Similarity	NPC470172
0.6991	Remote Similarity	NPC471254
0.6972	Remote Similarity	NPC470424
0.6961	Remote Similarity	NPC216941
0.6952	Remote Similarity	NPC476717
0.6944	Remote Similarity	NPC474699
0.6939	Remote Similarity	NPC215030
0.6939	Remote Similarity	NPC477867
0.6939	Remote Similarity	NPC125164
0.6937	Remote Similarity	NPC263674
0.6937	Remote Similarity	NPC261372
0.6937	Remote Similarity	NPC58267
0.693	Remote Similarity	NPC471253
0.693	Remote Similarity	NPC473406
0.6929	Remote Similarity	NPC188291
0.6923	Remote Similarity	NPC228190
0.6923	Remote Similarity	NPC236753
0.6911	Remote Similarity	NPC329008
0.6911	Remote Similarity	NPC317635
0.69	Remote Similarity	NPC474003
0.6869	Remote Similarity	NPC228411
0.686	Remote Similarity	NPC277583
0.6852	Remote Similarity	NPC477444
0.6852	Remote Similarity	NPC477442
0.6852	Remote Similarity	NPC477433
0.6847	Remote Similarity	NPC476728
0.6847	Remote Similarity	NPC193785
0.6833	Remote Similarity	NPC97002
0.6818	Remote Similarity	NPC247877
0.6818	Remote Similarity	NPC206878
0.6818	Remote Similarity	NPC309127
0.6792	Remote Similarity	NPC92139
0.6789	Remote Similarity	NPC469627
0.6789	Remote Similarity	NPC474065
0.6786	Remote Similarity	NPC472273
0.6783	Remote Similarity	NPC473148
0.678	Remote Similarity	NPC469825
0.6777	Remote Similarity	NPC308858
0.6777	Remote Similarity	NPC475537
0.6769	Remote Similarity	NPC100390
0.6769	Remote Similarity	NPC254614
0.6759	Remote Similarity	NPC477440
0.6759	Remote Similarity	NPC200580
0.6759	Remote Similarity	NPC477443
0.6757	Remote Similarity	NPC215570
0.6757	Remote Similarity	NPC287354
0.6757	Remote Similarity	NPC62407
0.6754	Remote Similarity	NPC298266
0.6754	Remote Similarity	NPC259654
0.6754	Remote Similarity	NPC67296
0.6754	Remote Similarity	NPC474053
0.6754	Remote Similarity	NPC304624
0.6735	Remote Similarity	NPC470243
0.6733	Remote Similarity	NPC83108
0.6733	Remote Similarity	NPC214030
0.6731	Remote Similarity	NPC148740
0.6731	Remote Similarity	NPC212340
0.6731	Remote Similarity	NPC102156
0.6729	Remote Similarity	NPC239938
0.6727	Remote Similarity	NPC475788
0.6724	Remote Similarity	NPC470167
0.6719	Remote Similarity	NPC2757
0.6698	Remote Similarity	NPC51267
0.6697	Remote Similarity	NPC65359
0.6696	Remote Similarity	NPC475765
0.6696	Remote Similarity	NPC116683
0.6696	Remote Similarity	NPC476009
0.6696	Remote Similarity	NPC475785
0.6696	Remote Similarity	NPC474297
0.6695	Remote Similarity	NPC224414
0.6695	Remote Similarity	NPC469826
0.6667	Remote Similarity	NPC475376
0.6667	Remote Similarity	NPC469824
0.6667	Remote Similarity	NPC215408
0.6667	Remote Similarity	NPC53158
0.6667	Remote Similarity	NPC471221
0.6667	Remote Similarity	NPC470117
0.664	Remote Similarity	NPC142882
0.664	Remote Similarity	NPC476849
0.6639	Remote Similarity	NPC227879
0.6639	Remote Similarity	NPC208333
0.6638	Remote Similarity	NPC34562
0.6637	Remote Similarity	NPC304445
0.6637	Remote Similarity	NPC236580
0.6636	Remote Similarity	NPC216137
0.6617	Remote Similarity	NPC256618
0.6617	Remote Similarity	NPC219058
0.6615	Remote Similarity	NPC264192
0.6612	Remote Similarity	NPC471570
0.6612	Remote Similarity	NPC312498
0.6612	Remote Similarity	NPC473849
0.6607	Remote Similarity	NPC475900
0.6607	Remote Similarity	NPC305808
0.6607	Remote Similarity	NPC322188
0.6604	Remote Similarity	NPC115995
0.6585	Remote Similarity	NPC213084
0.6585	Remote Similarity	NPC190185
0.6583	Remote Similarity	NPC106760
0.6583	Remote Similarity	NPC470622
0.6581	Remote Similarity	NPC469629
0.6577	Remote Similarity	NPC161035
0.6574	Remote Similarity	NPC475773
0.6571	Remote Similarity	NPC311642
0.6571	Remote Similarity	NPC100366
0.6571	Remote Similarity	NPC164289
0.6571	Remote Similarity	NPC242771
0.6569	Remote Similarity	NPC70996
0.6569	Remote Similarity	NPC188793
0.656	Remote Similarity	NPC258592
0.656	Remote Similarity	NPC319570
0.656	Remote Similarity	NPC178548
0.6557	Remote Similarity	NPC209058
0.6555	Remote Similarity	NPC475319
0.6555	Remote Similarity	NPC202898
0.6555	Remote Similarity	NPC92890
0.6555	Remote Similarity	NPC472079
0.6552	Remote Similarity	NPC80144
0.6542	Remote Similarity	NPC473350
0.6542	Remote Similarity	NPC476715

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 NPC469787 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	781
0.1-0.2	4587
0.2-0.3	2589
0.3-0.4	771
0.4-0.5	319
0.5-0.6	95
0.6-0.7	6
0.7-0.8	0
0.8-0.85	2
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8476	Intermediate Similarity	NPD4057	Clinical (unspecified phase)
0.8476	Intermediate Similarity	NPD4056	Clinical (unspecified phase)
0.6903	Remote Similarity	NPD1700	Approved
0.6581	Remote Similarity	NPD8170	Clinical (unspecified phase)
0.6346	Remote Similarity	NPD4238	Approved
0.6346	Remote Similarity	NPD4802	Phase 2
0.6336	Remote Similarity	NPD7078	Approved
0.6308	Remote Similarity	NPD7492	Approved
0.6271	Remote Similarity	NPD8085	Approved
0.6271	Remote Similarity	NPD8083	Approved
0.6271	Remote Similarity	NPD8139	Approved
0.6271	Remote Similarity	NPD8086	Approved
0.6271	Remote Similarity	NPD8082	Approved
0.6271	Remote Similarity	NPD8138	Approved
0.6271	Remote Similarity	NPD8084	Approved
0.626	Remote Similarity	NPD6616	Approved
0.625	Remote Similarity	NPD6059	Approved
0.625	Remote Similarity	NPD6054	Approved
0.6218	Remote Similarity	NPD8276	Approved
0.6218	Remote Similarity	NPD8275	Approved
0.6212	Remote Similarity	NPD8293	Discontinued
0.6202	Remote Similarity	NPD8267	Approved
0.6202	Remote Similarity	NPD8269	Approved
0.6202	Remote Similarity	NPD8268	Approved
0.6202	Remote Similarity	NPD8266	Approved
0.6167	Remote Similarity	NPD8081	Approved
0.6165	Remote Similarity	NPD7736	Approved
0.6154	Remote Similarity	NPD6370	Approved
0.6148	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6142	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6116	Remote Similarity	NPD8393	Approved
0.6077	Remote Similarity	NPD6015	Approved
0.6077	Remote Similarity	NPD6016	Approved
0.6066	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6031	Remote Similarity	NPD5988	Approved
0.6	Remote Similarity	NPD898	Approved
0.6	Remote Similarity	NPD897	Approved
0.6	Remote Similarity	NPD6319	Approved
0.6	Remote Similarity	NPD896	Approved
0.5985	Remote Similarity	NPD8328	Phase 3
0.5981	Remote Similarity	NPD7329	Approved
0.592	Remote Similarity	NPD6371	Approved
0.5882	Remote Similarity	NPD7319	Approved
0.5868	Remote Similarity	NPD8300	Approved
0.5868	Remote Similarity	NPD8301	Approved
0.5833	Remote Similarity	NPD8274	Clinical (unspecified phase)
0.5827	Remote Similarity	NPD6882	Approved
0.5812	Remote Similarity	NPD5282	Discontinued
0.5809	Remote Similarity	NPD6033	Approved
0.5806	Remote Similarity	NPD8307	Discontinued
0.5806	Remote Similarity	NPD8140	Approved
0.5789	Remote Similarity	NPD8080	Discontinued
0.5784	Remote Similarity	NPD229	Approved
0.5781	Remote Similarity	NPD8133	Approved
0.5778	Remote Similarity	NPD7507	Approved
0.5769	Remote Similarity	NPD6009	Approved
0.5766	Remote Similarity	NPD3670	Clinical (unspecified phase)
0.5766	Remote Similarity	NPD3669	Approved
0.5748	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.5727	Remote Similarity	NPD1779	Approved
0.5727	Remote Similarity	NPD1780	Approved
0.5726	Remote Similarity	NPD8171	Discontinued
0.5714	Remote Similarity	NPD6921	Approved
0.5714	Remote Similarity	NPD3181	Approved
0.5714	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.5714	Remote Similarity	NPD8305	Approved
0.5714	Remote Similarity	NPD8306	Approved
0.5714	Remote Similarity	NPD6372	Approved
0.5714	Remote Similarity	NPD6373	Approved
0.5703	Remote Similarity	NPD8297	Approved
0.57	Remote Similarity	NPD7909	Approved
0.568	Remote Similarity	NPD6412	Phase 2
0.5669	Remote Similarity	NPD8087	Discontinued
0.5635	Remote Similarity	NPD7320	Approved
0.5635	Remote Similarity	NPD6686	Approved
0.563	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.5625	Remote Similarity	NPD6649	Approved
0.5625	Remote Similarity	NPD6650	Approved
0.5607	Remote Similarity	NPD3702	Approved
0.56	Remote Similarity	NPD6402	Approved
0.56	Remote Similarity	NPD5739	Approved
0.56	Remote Similarity	NPD8961	Approved
0.56	Remote Similarity	NPD6675	Approved
0.56	Remote Similarity	NPD7128	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