NPASS Compound

Structure

NPC112752 OpenBabel07101718312D 38 42 0 0 1 0 0 0 0 0999 V2000 -3.5663 -3.9874 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -5.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4242 -2.6195 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9227 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5139 0.6235 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1123 1.1828 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3438 -3.0125 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.7321 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4888 0.4010 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4888 -1.4010 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.5139 -1.6235 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.7321 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.7321 -4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0017 -2.2594 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0000 -1.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8660 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -1.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.0000 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8660 -4.5000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -3.7470 2.1137 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.9977 -2.3491 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.2954 -0.1738 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -0.5000 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 17 1 0 0 0 0 4 28 1 0 0 0 0 5 28 1 0 0 0 0 6 31 1 0 0 0 0 7 8 2 0 0 0 0 7 9 1 0 0 0 0 8 10 1 0 0 0 0 9 19 2 0 0 0 0 10 23 2 0 0 0 0 11 15 2 0 0 0 0 11 21 1 0 0 0 0 12 18 1 0 0 0 0 13 18 2 0 0 0 0 13 22 1 0 0 0 0 14 18 1 0 0 0 0 14 32 1 0 0 0 0 15 24 1 0 0 0 0 16 26 1 0 0 0 0 16 29 1 1 0 0 0 17 33 2 0 0 0 0 17 38 1 0 0 0 0 19 23 1 0 0 0 0 19 27 1 0 0 0 0 20 12 1 1 0 0 0 20 21 1 0 0 0 0 20 24 1 0 0 0 0 21 29 1 6 0 0 0 22 25 1 0 0 0 0 22 29 1 1 0 0 0 23 31 1 0 0 0 0 24 34 2 0 0 0 0 25 28 1 0 0 0 0 25 30 1 1 0 0 0 26 30 1 6 0 0 0 26 37 1 0 0 0 0 27 35 2 0 0 0 0 27 37 1 0 0 0 0 28 30 1 0 0 0 0 29 36 1 1 0 0 0 30 38 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	523.26
Volume:	536.09
LogP:	3.768
LogD:	2.634
LogS:	-4.638
# Rotatable Bonds:	7
TPSA:	122.16
# H-Bond Aceptor:	8
# H-Bond Donor:	3
# Rings:	5
# Heavy Atoms:	8

MedChem Properties

QED Drug-Likeness Score:	0.397
Synthetic Accessibility Score:	4.997
Fsp3:	0.567
Lipinski Rule-of-5:	Accepted
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:	-5.077
MDCK Permeability:	2.943302388302982e-05
Pgp-inhibitor:	0.968
Pgp-substrate:	0.012
Human Intestinal Absorption (HIA):	0.29
20% Bioavailability (F20%):	0.018
30% Bioavailability (F30%):	0.495

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.25
Plasma Protein Binding (PPB):	73.229736328125%
Volume Distribution (VD):	1.058
Pgp-substrate:	32.19479751586914%

ADMET: Metabolism

CYP1A2-inhibitor:	0.146
CYP1A2-substrate:	0.086
CYP2C19-inhibitor:	0.443
CYP2C19-substrate:	0.316
CYP2C9-inhibitor:	0.87
CYP2C9-substrate:	0.072
CYP2D6-inhibitor:	0.168
CYP2D6-substrate:	0.141
CYP3A4-inhibitor:	0.895
CYP3A4-substrate:	0.234

ADMET: Excretion

Clearance (CL):	5.296
Half-life (T1/2):	0.681

ADMET: Toxicity

hERG Blockers:	0.838
Human Hepatotoxicity (H-HT):	0.983
Drug-inuced Liver Injury (DILI):	0.941
AMES Toxicity:	0.027
Rat Oral Acute Toxicity:	0.837
Maximum Recommended Daily Dose:	0.956
Skin Sensitization:	0.246
Carcinogencity:	0.024
Eye Corrosion:	0.003
Eye Irritation:	0.011
Respiratory Toxicity:	0.962

Download Data

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

Natural Product: NPC112752

Natural Product ID:	NPC112752
*Common Name:**	Sapintoxin A
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	KBSBUGUKMIUBEE-WQYXQGCUSA-N
Standard InCHI:	InChI=1S/C30H37NO7/c1-15-11-21-20(24(15)34)12-18(14-32)13-22-25-28(4,5)30(25,38-17(3)33)26(16(2)29(21,22)36)37-27(35)19-9-7-8-10-23(19)31-6/h7-11,13,16,20-22,25-26,31-32,36H,12,14H2,1-6H3/t16-,20+,21-,22+,25-,26-,29+,30-/m1/s1
SMILES:	CC1=C[C@@H]2[C@H](CC(=C[C@H]3[C@@H]4C(C)(C)[C@@]4([C@@H]([C@@H](C)[C@]23O)OC(=O)c2ccccc2NC)OC(=O)C)CO)C1=O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL503534
PubChem CID:	108085
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001551] Diterpenoids [CHEMONTID:0002875] Tigliane and ingenane diterpenoids

*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
NPO25366	Sapium indicum	Species	Euphorbiaceae	Eukaryota	Fruits	n.a.	n.a.	PMID[12713411]
NPO25366	Sapium indicum	Species	Euphorbiaceae	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	1

Activity Type	# Activity
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT88	Organism	Mycobacterium tuberculosis	Mycobacterium tuberculosis	MIC	=	3.12	ug.mL-1	PMID[518314]

☑ 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 NPC112752 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	249
0.1-0.2	1119
0.2-0.3	2810
0.3-0.4	7842
0.4-0.5	14783
0.5-0.6	14058
0.6-0.7	1754
0.7-0.8	60
0.8-0.85	13
0.85-0.9	0
0.9-0.95	0
0.95-1	9

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC311054
0.9831	High Similarity	NPC136573
0.9831	High Similarity	NPC107828
0.9831	High Similarity	NPC90358
0.9831	High Similarity	NPC176371
0.9829	High Similarity	NPC198205
0.9829	High Similarity	NPC21483
0.9718	High Similarity	NPC198390
0.873	High Similarity	NPC475223
0.8684	High Similarity	NPC246983
0.8684	High Similarity	NPC475448
0.8125	Intermediate Similarity	NPC476218
0.8125	Intermediate Similarity	NPC108804
0.8073	Intermediate Similarity	NPC476256
0.8073	Intermediate Similarity	NPC476212
0.8073	Intermediate Similarity	NPC476205
0.8073	Intermediate Similarity	NPC476206
0.8073	Intermediate Similarity	NPC476257
0.8073	Intermediate Similarity	NPC476129
0.8073	Intermediate Similarity	NPC476207
0.8073	Intermediate Similarity	NPC259791
0.7684	Intermediate Similarity	NPC132652
0.7644	Intermediate Similarity	NPC473837
0.7611	Intermediate Similarity	NPC469648
0.7611	Intermediate Similarity	NPC469647
0.7611	Intermediate Similarity	NPC22571
0.7611	Intermediate Similarity	NPC138641
0.7611	Intermediate Similarity	NPC283875
0.7514	Intermediate Similarity	NPC233581
0.7514	Intermediate Similarity	NPC145649
0.75	Intermediate Similarity	NPC140021
0.7488	Intermediate Similarity	NPC223590
0.7486	Intermediate Similarity	NPC11410
0.7459	Intermediate Similarity	NPC472398
0.7303	Intermediate Similarity	NPC183540
0.7302	Intermediate Similarity	NPC470971
0.729	Intermediate Similarity	NPC140311
0.7273	Intermediate Similarity	NPC473486
0.7273	Intermediate Similarity	NPC475316
0.7269	Intermediate Similarity	NPC473667
0.7235	Intermediate Similarity	NPC473850
0.7235	Intermediate Similarity	NPC475137
0.7235	Intermediate Similarity	NPC475498
0.723	Intermediate Similarity	NPC475408
0.723	Intermediate Similarity	NPC471014
0.723	Intermediate Similarity	NPC471016
0.7227	Intermediate Similarity	NPC35390
0.7227	Intermediate Similarity	NPC470631
0.7227	Intermediate Similarity	NPC473781
0.7222	Intermediate Similarity	NPC106593
0.72	Intermediate Similarity	NPC173295
0.72	Intermediate Similarity	NPC317882
0.72	Intermediate Similarity	NPC473300
0.72	Intermediate Similarity	NPC471754
0.72	Intermediate Similarity	NPC475336
0.72	Intermediate Similarity	NPC453583
0.7192	Intermediate Similarity	NPC36607
0.7189	Intermediate Similarity	NPC76565
0.7189	Intermediate Similarity	NPC57797
0.7189	Intermediate Similarity	NPC250807
0.7189	Intermediate Similarity	NPC114808
0.7186	Intermediate Similarity	NPC477998
0.7183	Intermediate Similarity	NPC470306
0.7169	Intermediate Similarity	NPC475601
0.7167	Intermediate Similarity	NPC477894
0.7167	Intermediate Similarity	NPC95449
0.7164	Intermediate Similarity	NPC67246
0.7164	Intermediate Similarity	NPC33372
0.7163	Intermediate Similarity	NPC301368
0.7163	Intermediate Similarity	NPC84815
0.7163	Intermediate Similarity	NPC216428
0.7151	Intermediate Similarity	NPC251139
0.715	Intermediate Similarity	NPC471623
0.7149	Intermediate Similarity	NPC96801
0.7149	Intermediate Similarity	NPC150698
0.7143	Intermediate Similarity	NPC253476
0.7136	Intermediate Similarity	NPC471190
0.7136	Intermediate Similarity	NPC475362
0.7136	Intermediate Similarity	NPC475644
0.7136	Intermediate Similarity	NPC470486
0.7136	Intermediate Similarity	NPC471977
0.713	Intermediate Similarity	NPC475426
0.713	Intermediate Similarity	NPC35208
0.7127	Intermediate Similarity	NPC34943
0.7117	Intermediate Similarity	NPC469748
0.7116	Intermediate Similarity	NPC62367
0.7116	Intermediate Similarity	NPC294579
0.7116	Intermediate Similarity	NPC144779
0.7114	Intermediate Similarity	NPC275170
0.7114	Intermediate Similarity	NPC306001
0.7114	Intermediate Similarity	NPC473400
0.7114	Intermediate Similarity	NPC324251
0.7114	Intermediate Similarity	NPC206211
0.7114	Intermediate Similarity	NPC471629
0.711	Intermediate Similarity	NPC471980
0.7109	Intermediate Similarity	NPC25961
0.7105	Intermediate Similarity	NPC253738
0.7103	Intermediate Similarity	NPC477907
0.7103	Intermediate Similarity	NPC42678
0.7103	Intermediate Similarity	NPC477909
0.71	Intermediate Similarity	NPC316405
0.7095	Intermediate Similarity	NPC100913
0.7095	Intermediate Similarity	NPC275592
0.7095	Intermediate Similarity	NPC90614
0.7091	Intermediate Similarity	NPC475631
0.7091	Intermediate Similarity	NPC328186
0.7091	Intermediate Similarity	NPC476110
0.7091	Intermediate Similarity	NPC211920
0.7091	Intermediate Similarity	NPC14116
0.7091	Intermediate Similarity	NPC475600
0.7091	Intermediate Similarity	NPC146824
0.7091	Intermediate Similarity	NPC122968
0.7091	Intermediate Similarity	NPC87152
0.7091	Intermediate Similarity	NPC285411
0.7091	Intermediate Similarity	NPC477787
0.7091	Intermediate Similarity	NPC228377
0.7091	Intermediate Similarity	NPC124029
0.7088	Intermediate Similarity	NPC92867
0.7088	Intermediate Similarity	NPC311825
0.7088	Intermediate Similarity	NPC125882
0.7078	Intermediate Similarity	NPC477902
0.7078	Intermediate Similarity	NPC328154
0.7071	Intermediate Similarity	NPC97584
0.707	Intermediate Similarity	NPC6981
0.7064	Intermediate Similarity	NPC127720
0.7064	Intermediate Similarity	NPC127026
0.7062	Intermediate Similarity	NPC48042
0.7062	Intermediate Similarity	NPC472550
0.7062	Intermediate Similarity	NPC304179
0.7059	Intermediate Similarity	NPC134384
0.7059	Intermediate Similarity	NPC215892
0.7059	Intermediate Similarity	NPC242662
0.7059	Intermediate Similarity	NPC311196
0.7059	Intermediate Similarity	NPC191193
0.7059	Intermediate Similarity	NPC321072
0.7056	Intermediate Similarity	NPC41481
0.7056	Intermediate Similarity	NPC472576
0.7056	Intermediate Similarity	NPC27377
0.7056	Intermediate Similarity	NPC4421
0.7056	Intermediate Similarity	NPC97947
0.7056	Intermediate Similarity	NPC291599
0.7056	Intermediate Similarity	NPC118080
0.7056	Intermediate Similarity	NPC87448
0.7049	Intermediate Similarity	NPC240115
0.7049	Intermediate Similarity	NPC20255
0.7045	Intermediate Similarity	NPC473506
0.7042	Intermediate Similarity	NPC472553
0.704	Intermediate Similarity	NPC30456
0.7039	Intermediate Similarity	NPC9905
0.7035	Intermediate Similarity	NPC49184
0.7024	Intermediate Similarity	NPC208553
0.7024	Intermediate Similarity	NPC181964
0.7024	Intermediate Similarity	NPC471606
0.7023	Intermediate Similarity	NPC477910
0.7018	Intermediate Similarity	NPC477912
0.7017	Intermediate Similarity	NPC192658
0.7015	Intermediate Similarity	NPC327699
0.7014	Intermediate Similarity	NPC63041
0.7009	Intermediate Similarity	NPC237702
0.7004	Intermediate Similarity	NPC253482
0.7	Intermediate Similarity	NPC472547
0.7	Intermediate Similarity	NPC87934
0.7	Intermediate Similarity	NPC171207
0.7	Intermediate Similarity	NPC97667
0.7	Intermediate Similarity	NPC162613
0.6996	Remote Similarity	NPC316841
0.6996	Remote Similarity	NPC292416
0.6996	Remote Similarity	NPC473689
0.6996	Remote Similarity	NPC475596
0.6996	Remote Similarity	NPC475303
0.6995	Remote Similarity	NPC30171
0.699	Remote Similarity	NPC473558
0.6989	Remote Similarity	NPC471103
0.6989	Remote Similarity	NPC197037
0.6986	Remote Similarity	NPC477788
0.6983	Remote Similarity	NPC39549
0.6978	Remote Similarity	NPC170751
0.6978	Remote Similarity	NPC163087
0.6977	Remote Similarity	NPC264674
0.6977	Remote Similarity	NPC228331
0.6968	Remote Similarity	NPC473632
0.6968	Remote Similarity	NPC132599
0.6968	Remote Similarity	NPC469730
0.6966	Remote Similarity	NPC477893
0.6964	Remote Similarity	NPC319880
0.6964	Remote Similarity	NPC244839
0.6964	Remote Similarity	NPC320324
0.6961	Remote Similarity	NPC16912
0.6959	Remote Similarity	NPC212768
0.6959	Remote Similarity	NPC6576
0.6959	Remote Similarity	NPC473115
0.6959	Remote Similarity	NPC75600
0.6959	Remote Similarity	NPC158020
0.6959	Remote Similarity	NPC473089
0.6957	Remote Similarity	NPC473602
0.6957	Remote Similarity	NPC94602
0.6957	Remote Similarity	NPC312393
0.6957	Remote Similarity	NPC478263
0.6946	Remote Similarity	NPC25401
0.694	Remote Similarity	NPC38696

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 NPC112752 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	172
0.1-0.2	536
0.2-0.3	819
0.3-0.4	1736
0.4-0.5	3613
0.5-0.6	2046
0.6-0.7	224
0.7-0.8	4
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.7253	Intermediate Similarity	NPD2737	Clinical (unspecified phase)
0.7243	Intermediate Similarity	NPD2836	Approved
0.7236	Intermediate Similarity	NPD8360	Approved
0.7236	Intermediate Similarity	NPD8361	Approved
0.7222	Intermediate Similarity	NPD8424	Clinical (unspecified phase)
0.715	Intermediate Similarity	NPD8435	Approved
0.7059	Intermediate Similarity	NPD2672	Discontinued
0.7024	Intermediate Similarity	NPD8485	Approved
0.7024	Intermediate Similarity	NPD7238	Clinical (unspecified phase)
0.7017	Intermediate Similarity	NPD1625	Approved
0.7011	Intermediate Similarity	NPD4888	Discontinued
0.695	Remote Similarity	NPD8407	Phase 2
0.6923	Remote Similarity	NPD8486	Clinical (unspecified phase)
0.6919	Remote Similarity	NPD7528	Approved
0.6908	Remote Similarity	NPD4668	Phase 2
0.6897	Remote Similarity	NPD5928	Phase 1
0.6884	Remote Similarity	NPD8368	Discontinued
0.6862	Remote Similarity	NPD5086	Approved
0.685	Remote Similarity	NPD7962	Phase 2
0.6825	Remote Similarity	NPD7597	Clinical (unspecified phase)
0.6818	Remote Similarity	NPD8470	Clinical (unspecified phase)
0.6802	Remote Similarity	NPD5466	Approved
0.6796	Remote Similarity	NPD1626	Approved
0.6766	Remote Similarity	NPD8658	Clinical (unspecified phase)
0.6753	Remote Similarity	NPD5430	Discontinued
0.6714	Remote Similarity	NPD6874	Approved
0.6685	Remote Similarity	NPD1189	Approved
0.6667	Remote Similarity	NPD5997	Discontinued
0.6667	Remote Similarity	NPD5197	Approved
0.6667	Remote Similarity	NPD7295	Approved
0.6667	Remote Similarity	NPD5194	Approved
0.6667	Remote Similarity	NPD5196	Approved
0.6667	Remote Similarity	NPD7606	Phase 3
0.6651	Remote Similarity	NPD7880	Clinical (unspecified phase)
0.6633	Remote Similarity	NPD5919	Clinical (unspecified phase)
0.6599	Remote Similarity	NPD2821	Approved
0.6595	Remote Similarity	NPD6414	Clinical (unspecified phase)
0.6593	Remote Similarity	NPD3528	Clinical (unspecified phase)
0.6592	Remote Similarity	NPD5433	Clinical (unspecified phase)
0.6587	Remote Similarity	NPD5937	Approved
0.6575	Remote Similarity	NPD8462	Phase 1
0.6575	Remote Similarity	NPD6657	Clinical (unspecified phase)
0.6567	Remote Similarity	NPD5498	Phase 2
0.6562	Remote Similarity	NPD8155	Clinical (unspecified phase)
0.6557	Remote Similarity	NPD2670	Approved
0.6544	Remote Similarity	NPD7302	Phase 3
0.6544	Remote Similarity	NPD7300	Phase 3
0.6532	Remote Similarity	NPD8404	Phase 2
0.6512	Remote Similarity	NPD7497	Discontinued
0.6508	Remote Similarity	NPD1802	Approved
0.6508	Remote Similarity	NPD7478	Approved
0.6508	Remote Similarity	NPD1801	Approved
0.6507	Remote Similarity	NPD8146	Phase 2
0.6507	Remote Similarity	NPD7570	Approved
0.6507	Remote Similarity	NPD7569	Approved
0.6494	Remote Similarity	NPD7922	Phase 1
0.6492	Remote Similarity	NPD1230	Approved
0.6489	Remote Similarity	NPD7274	Clinical (unspecified phase)
0.6479	Remote Similarity	NPD5608	Approved
0.6479	Remote Similarity	NPD5609	Approved
0.6471	Remote Similarity	NPD3794	Approved
0.6471	Remote Similarity	NPD3795	Approved
0.6455	Remote Similarity	NPD7236	Approved
0.6445	Remote Similarity	NPD7256	Discontinued
0.6438	Remote Similarity	NPD4506	Discontinued
0.6436	Remote Similarity	NPD7487	Discontinued
0.6432	Remote Similarity	NPD3170	Approved
0.6429	Remote Similarity	NPD8468	Phase 2
0.6425	Remote Similarity	NPD6591	Clinical (unspecified phase)
0.6419	Remote Similarity	NPD7476	Discontinued
0.6418	Remote Similarity	NPD3451	Clinical (unspecified phase)
0.6415	Remote Similarity	NPD5411	Discontinued
0.6408	Remote Similarity	NPD7546	Discontinued
0.64	Remote Similarity	NPD2899	Discontinued
0.6394	Remote Similarity	NPD6793	Clinical (unspecified phase)
0.6393	Remote Similarity	NPD4082	Approved
0.6385	Remote Similarity	NPD5195	Discontinued
0.6383	Remote Similarity	NPD7082	Approved
0.638	Remote Similarity	NPD1945	Phase 1
0.638	Remote Similarity	NPD4493	Discontinued
0.6377	Remote Similarity	NPD6021	Clinical (unspecified phase)
0.6373	Remote Similarity	NPD7239	Suspended
0.6368	Remote Similarity	NPD4607	Approved
0.6368	Remote Similarity	NPD5242	Approved
0.6364	Remote Similarity	NPD7693	Approved
0.6354	Remote Similarity	NPD4513	Discontinued
0.6352	Remote Similarity	NPD6723	Discontinued
0.6349	Remote Similarity	NPD7259	Approved
0.6349	Remote Similarity	NPD2387	Approved
0.6347	Remote Similarity	NPD6973	Clinical (unspecified phase)
0.6345	Remote Similarity	NPD7244	Discontinued
0.6313	Remote Similarity	NPD1574	Approved
0.6313	Remote Similarity	NPD956	Clinical (unspecified phase)
0.6311	Remote Similarity	NPD7038	Approved
0.6311	Remote Similarity	NPD7039	Approved
0.6308	Remote Similarity	NPD3684	Discontinued
0.6303	Remote Similarity	NPD5042	Phase 1
0.6301	Remote Similarity	NPD7999	Approved
0.6296	Remote Similarity	NPD6519	Phase 2
0.6296	Remote Similarity	NPD2820	Phase 3
0.6295	Remote Similarity	NPD4562	Clinical (unspecified phase)
0.6293	Remote Similarity	NPD4981	Phase 2
0.6291	Remote Similarity	NPD6534	Approved
0.6291	Remote Similarity	NPD6535	Approved
0.6287	Remote Similarity	NPD1913	Phase 1
0.6279	Remote Similarity	NPD7699	Phase 2
0.6279	Remote Similarity	NPD7700	Phase 2
0.6278	Remote Similarity	NPD7301	Phase 3
0.6277	Remote Similarity	NPD7702	Clinical (unspecified phase)
0.6275	Remote Similarity	NPD7799	Discontinued
0.6273	Remote Similarity	NPD4596	Phase 1
0.6263	Remote Similarity	NPD7600	Phase 2
0.6261	Remote Similarity	NPD3893	Discontinued
0.6256	Remote Similarity	NPD7891	Discontinued
0.6256	Remote Similarity	NPD4575	Clinical (unspecified phase)
0.625	Remote Similarity	NPD6758	Approved
0.6244	Remote Similarity	NPD5610	Approved
0.6243	Remote Similarity	NPD2365	Approved
0.6239	Remote Similarity	NPD3949	Clinical (unspecified phase)
0.6238	Remote Similarity	NPD3863	Clinical (unspecified phase)
0.6238	Remote Similarity	NPD5186	Approved
0.6238	Remote Similarity	NPD8434	Phase 2
0.6238	Remote Similarity	NPD8150	Discontinued
0.6238	Remote Similarity	NPD5183	Approved
0.6238	Remote Similarity	NPD6891	Phase 2
0.6238	Remote Similarity	NPD6483	Approved
0.6238	Remote Similarity	NPD6484	Approved
0.6231	Remote Similarity	NPD1210	Approved
0.6222	Remote Similarity	NPD7930	Approved
0.622	Remote Similarity	NPD8167	Discontinued
0.6219	Remote Similarity	NPD8002	Clinical (unspecified phase)
0.6219	Remote Similarity	NPD8003	Clinical (unspecified phase)
0.6218	Remote Similarity	NPD4161	Discontinued
0.6213	Remote Similarity	NPD6625	Approved
0.6212	Remote Similarity	NPD7599	Phase 2
0.6212	Remote Similarity	NPD7114	Clinical (unspecified phase)
0.6211	Remote Similarity	NPD7292	Approved
0.6211	Remote Similarity	NPD7878	Phase 2
0.621	Remote Similarity	NPD6176	Phase 1
0.621	Remote Similarity	NPD7435	Discontinued
0.6205	Remote Similarity	NPD4492	Approved
0.6205	Remote Similarity	NPD3399	Approved
0.6205	Remote Similarity	NPD3888	Discontinued
0.6205	Remote Similarity	NPD4494	Approved
0.6202	Remote Similarity	NPD3253	Clinical (unspecified phase)
0.6199	Remote Similarity	NPD5143	Clinical (unspecified phase)
0.6199	Remote Similarity	NPD6296	Discontinued
0.6199	Remote Similarity	NPD7583	Approved
0.6198	Remote Similarity	NPD4041	Approved
0.6197	Remote Similarity	NPD8067	Phase 3
0.6193	Remote Similarity	NPD6570	Approved
0.6193	Remote Similarity	NPD7105	Phase 1
0.6193	Remote Similarity	NPD6571	Approved
0.619	Remote Similarity	NPD3154	Approved
0.619	Remote Similarity	NPD8055	Clinical (unspecified phase)
0.619	Remote Similarity	NPD3153	Approved
0.6188	Remote Similarity	NPD9567	Approved
0.6188	Remote Similarity	NPD552	Approved
0.6188	Remote Similarity	NPD553	Approved
0.6186	Remote Similarity	NPD9509	Clinical (unspecified phase)
0.6184	Remote Similarity	NPD6496	Clinical (unspecified phase)
0.6184	Remote Similarity	NPD5496	Approved
0.6182	Remote Similarity	NPD8320	Phase 1
0.6182	Remote Similarity	NPD8319	Approved
0.6182	Remote Similarity	NPD1294	Discontinued
0.6179	Remote Similarity	NPD7235	Clinical (unspecified phase)
0.6178	Remote Similarity	NPD4455	Discontinued
0.6176	Remote Similarity	NPD7997	Clinical (unspecified phase)
0.6175	Remote Similarity	NPD7565	Approved
0.6172	Remote Similarity	NPD4412	Phase 2
0.6171	Remote Similarity	NPD2509	Approved
0.6171	Remote Similarity	NPD2510	Approved
0.6171	Remote Similarity	NPD3472	Approved
0.6171	Remote Similarity	NPD4022	Approved
0.6171	Remote Similarity	NPD7585	Approved
0.617	Remote Similarity	NPD1109	Approved
0.617	Remote Similarity	NPD1110	Approved
0.6169	Remote Similarity	NPD7035	Approved
0.6169	Remote Similarity	NPD7036	Phase 3
0.6166	Remote Similarity	NPD3352	Approved
0.6161	Remote Similarity	NPD4948	Discontinued
0.6158	Remote Similarity	NPD2369	Discontinued
0.6158	Remote Similarity	NPD7795	Phase 2
0.6158	Remote Similarity	NPD2923	Approved
0.6157	Remote Similarity	NPD7858	Clinical (unspecified phase)
0.6157	Remote Similarity	NPD3280	Approved
0.6154	Remote Similarity	NPD3470	Approved
0.6154	Remote Similarity	NPD3471	Approved
0.615	Remote Similarity	NPD6659	Phase 2
0.6147	Remote Similarity	NPD6776	Approved
0.6147	Remote Similarity	NPD6779	Approved
0.6147	Remote Similarity	NPD6781	Approved
0.6147	Remote Similarity	NPD6782	Approved
0.6147	Remote Similarity	NPD6780	Approved
0.6147	Remote Similarity	NPD6777	Approved
0.6147	Remote Similarity	NPD6778	Approved
0.6146	Remote Similarity	NPD6185	Discontinued
0.6145	Remote Similarity	NPD7708	Approved
0.6143	Remote Similarity	NPD6163	Clinical (unspecified phase)
0.6136	Remote Similarity	NPD7064	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