NPASS Compound

Structure

NPC472430 OpenBabel07101719512D 30 33 0 0 1 0 0 0 0 0999 V2000 -4.2365 -10.7446 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6096 -7.0904 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7906 -5.3679 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8298 -9.8311 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8352 -9.7266 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4285 -8.8130 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4340 -8.7085 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0272 -7.7949 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3893 -4.3498 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3948 -4.2453 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2083 -6.0724 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8090 -1.4013 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6150 -6.9859 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.7961 -5.2634 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1691 -1.6092 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0119 -3.3317 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6456 0.5933 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7796 1.0933 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.6456 -0.4067 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.9135 0.5933 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.7796 -0.9067 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.6691 -0.7431 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 0.9135 -0.4067 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.5759 -2.5227 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 1.0064 -3.2272 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.5116 1.0933 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.6637 -0.6386 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.9135 1.5933 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.6456 -1.4067 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 4 1 0 0 0 0 3 14 1 0 0 0 0 4 5 1 0 0 0 0 5 6 1 0 0 0 0 6 7 1 0 0 0 0 7 8 1 0 0 0 0 8 13 1 0 0 0 0 9 10 2 0 0 0 0 9 14 1 0 0 0 0 10 16 1 0 0 0 0 11 13 1 0 0 0 0 11 14 2 0 0 0 0 12 15 1 0 0 0 0 13 2 1 1 0 0 0 15 22 1 0 0 0 0 15 24 1 6 0 0 0 16 24 2 3 0 0 0 16 25 1 0 0 0 0 17 26 2 0 0 0 0 18 17 1 6 0 0 0 18 20 1 0 0 0 0 18 28 1 0 0 0 0 19 17 1 6 0 0 0 19 21 1 0 0 0 0 19 29 1 0 0 0 0 20 23 1 6 0 0 0 20 28 1 0 0 0 0 21 23 1 6 0 0 0 21 29 1 0 0 0 0 22 27 1 0 0 0 0 22 30 1 0 0 0 0 23 12 1 6 0 0 0 23 30 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	419.23
Volume:	425.331
LogP:	2.44
LogD:	1.112
LogS:	-2.497
# Rotatable Bonds:	10
TPSA:	100.69
# H-Bond Aceptor:	7
# H-Bond Donor:	2
# Rings:	4
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.338
Synthetic Accessibility Score:	5.508
Fsp3:	0.739
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:	-4.837
MDCK Permeability:	3.646508776000701e-05
Pgp-inhibitor:	0.257
Pgp-substrate:	0.644
Human Intestinal Absorption (HIA):	0.47
20% Bioavailability (F20%):	0.149
30% Bioavailability (F30%):	0.064

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.144
Plasma Protein Binding (PPB):	86.8263168334961%
Volume Distribution (VD):	2.33
Pgp-substrate:	14.617792129516602%

ADMET: Metabolism

CYP1A2-inhibitor:	0.017
CYP1A2-substrate:	0.214
CYP2C19-inhibitor:	0.261
CYP2C19-substrate:	0.645
CYP2C9-inhibitor:	0.324
CYP2C9-substrate:	0.06
CYP2D6-inhibitor:	0.013
CYP2D6-substrate:	0.521
CYP3A4-inhibitor:	0.412
CYP3A4-substrate:	0.234

ADMET: Excretion

Clearance (CL):	6.621
Half-life (T1/2):	0.743

ADMET: Toxicity

hERG Blockers:	0.071
Human Hepatotoxicity (H-HT):	0.554
Drug-inuced Liver Injury (DILI):	0.584
AMES Toxicity:	0.034
Rat Oral Acute Toxicity:	0.907
Maximum Recommended Daily Dose:	0.671
Skin Sensitization:	0.808
Carcinogencity:	0.176
Eye Corrosion:	0.004
Eye Irritation:	0.017
Respiratory Toxicity:	0.518

Download Data

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

Natural Product: NPC472430

Natural Product ID:	NPC472430
*Common Name:**	JHTWWPWUODMKEO-NDMFEFOCSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	JHTWWPWUODMKEO-NDMFEFOCSA-N
Standard InCHI:	InChI=1S/C23H33NO6/c1-4-5-6-7-8-13(2)11-14(3)9-10-16(25)24-15-12-23(30-22(15)27)20-18(28-20)17(26)19-21(23)29-19/h9-11,13,15,18-22,27H,4-8,12H2,1-3H3,(H,24,25)/b10-9+,14-11+/t13-,15+,18-,19+,20-,21+,22?,23+/m1/s1
SMILES:	CCCCCC[C@H](/C=C(/C=C/C(=N[C@H]1C[C@]2(OC1O)[C@@H]1O[C@@H]1C(=O)[C@H]1[C@@H]2O1)O)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3402609
PubChem CID:	n.a.
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0001729] Oxepanes

*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
NPO33119	gymnascella dankaliensis	Species	Gymnoascaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17067147]
NPO33119	gymnascella dankaliensis	Species	Gymnoascaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17988094]
NPO33119	gymnascella dankaliensis	Species	Gymnoascaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18284207]
NPO33119	gymnascella dankaliensis	Species	Gymnoascaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25600409]

☑ 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
IC50	1

Activity Type	# Activity
Cell Line	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1864	Cell Line	L5178Y	Mus musculus	IC50	=	580.0	nM	PMID[570102]

☑ 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 NPC472430 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	148
0.1-0.2	801
0.2-0.3	3468
0.3-0.4	15734
0.4-0.5	17038
0.5-0.6	5037
0.6-0.7	455
0.7-0.8	14
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.976	High Similarity	NPC472428
0.8195	Intermediate Similarity	NPC164476
0.8195	Intermediate Similarity	NPC121601
0.8195	Intermediate Similarity	NPC471471
0.7808	Intermediate Similarity	NPC475837
0.7426	Intermediate Similarity	NPC280498
0.7292	Intermediate Similarity	NPC230889
0.7279	Intermediate Similarity	NPC469515
0.7246	Intermediate Similarity	NPC469494
0.7133	Intermediate Similarity	NPC314361
0.7092	Intermediate Similarity	NPC329919
0.7092	Intermediate Similarity	NPC477793
0.7083	Intermediate Similarity	NPC78189
0.7023	Intermediate Similarity	NPC70235
0.702	Intermediate Similarity	NPC77481
0.702	Intermediate Similarity	NPC233770
0.7007	Intermediate Similarity	NPC323532
0.7	Intermediate Similarity	NPC314451
0.7	Intermediate Similarity	NPC313342
0.7	Intermediate Similarity	NPC313333
0.7	Intermediate Similarity	NPC314512
0.6985	Remote Similarity	NPC147707
0.6963	Remote Similarity	NPC80650
0.695	Remote Similarity	NPC225049
0.6923	Remote Similarity	NPC100612
0.6923	Remote Similarity	NPC475599
0.6923	Remote Similarity	NPC174336
0.6923	Remote Similarity	NPC113620
0.6923	Remote Similarity	NPC187497
0.6913	Remote Similarity	NPC172365
0.6913	Remote Similarity	NPC82931
0.6913	Remote Similarity	NPC210729
0.6887	Remote Similarity	NPC475892
0.6883	Remote Similarity	NPC36463
0.6883	Remote Similarity	NPC298005
0.6879	Remote Similarity	NPC204639
0.6871	Remote Similarity	NPC145899
0.6866	Remote Similarity	NPC29501
0.6859	Remote Similarity	NPC475527
0.6859	Remote Similarity	NPC265699
0.6849	Remote Similarity	NPC76999
0.6846	Remote Similarity	NPC215988
0.6842	Remote Similarity	NPC214821
0.6842	Remote Similarity	NPC298067
0.6828	Remote Similarity	NPC139585
0.6821	Remote Similarity	NPC475394
0.6821	Remote Similarity	NPC475584
0.6821	Remote Similarity	NPC475152
0.6803	Remote Similarity	NPC75318
0.6788	Remote Similarity	NPC30196
0.6783	Remote Similarity	NPC314282
0.6783	Remote Similarity	NPC204556
0.6779	Remote Similarity	NPC200788
0.6779	Remote Similarity	NPC243680
0.6753	Remote Similarity	NPC244380
0.6753	Remote Similarity	NPC61717
0.6739	Remote Similarity	NPC6531
0.6719	Remote Similarity	NPC236176
0.6712	Remote Similarity	NPC316401
0.6712	Remote Similarity	NPC475472
0.669	Remote Similarity	NPC316133
0.669	Remote Similarity	NPC318445
0.6689	Remote Similarity	NPC99864
0.6667	Remote Similarity	NPC119794
0.6667	Remote Similarity	NPC193579
0.6667	Remote Similarity	NPC298469
0.6667	Remote Similarity	NPC23963
0.6667	Remote Similarity	NPC73829
0.6667	Remote Similarity	NPC141669
0.6644	Remote Similarity	NPC475314
0.6644	Remote Similarity	NPC477189
0.6644	Remote Similarity	NPC475606
0.6644	Remote Similarity	NPC251564
0.6644	Remote Similarity	NPC68282
0.6642	Remote Similarity	NPC475150
0.6623	Remote Similarity	NPC302276
0.6623	Remote Similarity	NPC265908
0.6623	Remote Similarity	NPC180770
0.6622	Remote Similarity	NPC120420
0.6619	Remote Similarity	NPC477116
0.6619	Remote Similarity	NPC296822
0.6619	Remote Similarity	NPC27999
0.6617	Remote Similarity	NPC475918
0.6599	Remote Similarity	NPC473485
0.6599	Remote Similarity	NPC474508
0.6596	Remote Similarity	NPC475003
0.6577	Remote Similarity	NPC280941
0.6577	Remote Similarity	NPC235772
0.6575	Remote Similarity	NPC315387
0.6575	Remote Similarity	NPC476851
0.6575	Remote Similarity	NPC316205
0.6573	Remote Similarity	NPC16709
0.6573	Remote Similarity	NPC315783
0.6573	Remote Similarity	NPC314629
0.6569	Remote Similarity	NPC469865
0.6569	Remote Similarity	NPC261750
0.6569	Remote Similarity	NPC1111
0.6558	Remote Similarity	NPC160222
0.6558	Remote Similarity	NPC193753
0.6552	Remote Similarity	NPC471940
0.6547	Remote Similarity	NPC474333
0.6536	Remote Similarity	NPC162910
0.6533	Remote Similarity	NPC243902
0.6531	Remote Similarity	NPC476852
0.6525	Remote Similarity	NPC313802
0.6525	Remote Similarity	NPC67917
0.6525	Remote Similarity	NPC470186
0.6525	Remote Similarity	NPC314268
0.6525	Remote Similarity	NPC477515
0.6512	Remote Similarity	NPC279722
0.651	Remote Similarity	NPC471136
0.651	Remote Similarity	NPC475154
0.651	Remote Similarity	NPC182266
0.651	Remote Similarity	NPC477072
0.651	Remote Similarity	NPC473548
0.651	Remote Similarity	NPC471137
0.651	Remote Similarity	NPC475500
0.651	Remote Similarity	NPC223356
0.651	Remote Similarity	NPC100017
0.6507	Remote Similarity	NPC476091
0.6507	Remote Similarity	NPC476859
0.6507	Remote Similarity	NPC476078
0.6503	Remote Similarity	NPC469943
0.6496	Remote Similarity	NPC476023
0.6494	Remote Similarity	NPC803
0.6493	Remote Similarity	NPC201128
0.6489	Remote Similarity	NPC324667
0.6486	Remote Similarity	NPC90814
0.6486	Remote Similarity	NPC96425
0.6486	Remote Similarity	NPC189393
0.6483	Remote Similarity	NPC471939
0.6475	Remote Similarity	NPC471645
0.6471	Remote Similarity	NPC474725
0.6463	Remote Similarity	NPC162495
0.6463	Remote Similarity	NPC476854
0.6452	Remote Similarity	NPC69176
0.6452	Remote Similarity	NPC284625
0.6449	Remote Similarity	NPC60432
0.6447	Remote Similarity	NPC476558
0.6444	Remote Similarity	NPC474716
0.6444	Remote Similarity	NPC469558
0.6429	Remote Similarity	NPC476710
0.6429	Remote Similarity	NPC476711
0.6429	Remote Similarity	NPC179626
0.6423	Remote Similarity	NPC46407
0.6419	Remote Similarity	NPC476855
0.6419	Remote Similarity	NPC476863
0.6419	Remote Similarity	NPC476862
0.6419	Remote Similarity	NPC475389
0.6419	Remote Similarity	NPC473838
0.6414	Remote Similarity	NPC473919
0.6414	Remote Similarity	NPC473709
0.6403	Remote Similarity	NPC477266
0.6398	Remote Similarity	NPC4108
0.6391	Remote Similarity	NPC477198
0.6383	Remote Similarity	NPC316325
0.6383	Remote Similarity	NPC476713
0.6383	Remote Similarity	NPC476712
0.6377	Remote Similarity	NPC194619
0.6377	Remote Similarity	NPC170375
0.6376	Remote Similarity	NPC475139
0.6376	Remote Similarity	NPC470185
0.6376	Remote Similarity	NPC180902
0.637	Remote Similarity	NPC217901
0.6369	Remote Similarity	NPC316249
0.6357	Remote Similarity	NPC73314
0.635	Remote Similarity	NPC473578
0.6345	Remote Similarity	NPC473802
0.6338	Remote Similarity	NPC9714
0.6338	Remote Similarity	NPC240509
0.6331	Remote Similarity	NPC473877
0.6327	Remote Similarity	NPC470780
0.6327	Remote Similarity	NPC475273
0.6327	Remote Similarity	NPC168849
0.6324	Remote Similarity	NPC475800
0.6324	Remote Similarity	NPC477513
0.6319	Remote Similarity	NPC475383
0.6319	Remote Similarity	NPC472401
0.6319	Remote Similarity	NPC315915
0.6319	Remote Similarity	NPC477046
0.6319	Remote Similarity	NPC102822
0.6319	Remote Similarity	NPC156379
0.6316	Remote Similarity	NPC305085
0.6316	Remote Similarity	NPC84042
0.6312	Remote Similarity	NPC477509
0.6304	Remote Similarity	NPC474586
0.6304	Remote Similarity	NPC281624
0.6304	Remote Similarity	NPC473975
0.6304	Remote Similarity	NPC473843
0.6304	Remote Similarity	NPC473594
0.6296	Remote Similarity	NPC74035
0.6296	Remote Similarity	NPC471143
0.6296	Remote Similarity	NPC477510
0.6294	Remote Similarity	NPC241050
0.6294	Remote Similarity	NPC268958
0.6291	Remote Similarity	NPC471234
0.6291	Remote Similarity	NPC242486
0.6291	Remote Similarity	NPC15215
0.6284	Remote Similarity	NPC236999
0.6277	Remote Similarity	NPC14862

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 NPC472430 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	109
0.1-0.2	591
0.2-0.3	3095
0.3-0.4	3912
0.4-0.5	1124
0.5-0.6	288
0.6-0.7	31
0.7-0.8	0
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
0.7	Intermediate Similarity	NPD8340	Approved
0.7	Intermediate Similarity	NPD8342	Approved
0.7	Intermediate Similarity	NPD8299	Approved
0.7	Intermediate Similarity	NPD8341	Approved
0.6831	Remote Similarity	NPD8451	Approved
0.6783	Remote Similarity	NPD8448	Approved
0.6759	Remote Similarity	NPD8390	Approved
0.6759	Remote Similarity	NPD8391	Approved
0.6759	Remote Similarity	NPD8392	Approved
0.6757	Remote Similarity	NPD8387	Clinical (unspecified phase)
0.6742	Remote Similarity	NPD5357	Phase 1
0.669	Remote Similarity	NPD7642	Approved
0.6689	Remote Similarity	NPD8415	Approved
0.6573	Remote Similarity	NPD7830	Approved
0.6573	Remote Similarity	NPD7829	Approved
0.6571	Remote Similarity	NPD7641	Discontinued
0.6552	Remote Similarity	NPD8074	Phase 3
0.6549	Remote Similarity	NPD8444	Approved
0.6549	Remote Similarity	NPD8274	Clinical (unspecified phase)
0.6544	Remote Similarity	NPD6421	Discontinued
0.6531	Remote Similarity	NPD6914	Discontinued
0.6503	Remote Similarity	NPD8080	Discontinued
0.6383	Remote Similarity	NPD7500	Approved
0.6377	Remote Similarity	NPD7601	Clinical (unspecified phase)
0.634	Remote Similarity	NPD6334	Approved
0.634	Remote Similarity	NPD6333	Approved
0.6333	Remote Similarity	NPD8338	Approved
0.6268	Remote Similarity	NPD8137	Clinical (unspecified phase)
0.6259	Remote Similarity	NPD8273	Phase 1
0.625	Remote Similarity	NPD3168	Discontinued
0.6218	Remote Similarity	NPD8384	Approved
0.6207	Remote Similarity	NPD8517	Approved
0.6207	Remote Similarity	NPD6921	Approved
0.6207	Remote Similarity	NPD8516	Approved
0.6207	Remote Similarity	NPD8515	Approved
0.6207	Remote Similarity	NPD8513	Phase 3
0.6164	Remote Similarity	NPD6370	Approved
0.6136	Remote Similarity	NPD7839	Suspended
0.6089	Remote Similarity	NPD8407	Phase 2
0.6077	Remote Similarity	NPD7983	Approved
0.6029	Remote Similarity	NPD8300	Approved
0.6029	Remote Similarity	NPD8301	Approved
0.6027	Remote Similarity	NPD6054	Approved
0.6025	Remote Similarity	NPD2575	Approved
0.6024	Remote Similarity	NPD8414	Discontinued
0.6	Remote Similarity	NPD6648	Approved
0.6	Remote Similarity	NPD8522	Clinical (unspecified phase)
0.5986	Remote Similarity	NPD8269	Approved
0.5986	Remote Similarity	NPD8268	Approved
0.5986	Remote Similarity	NPD8267	Approved
0.5986	Remote Similarity	NPD8266	Approved
0.5985	Remote Similarity	NPD8275	Approved
0.5985	Remote Similarity	NPD8276	Approved
0.5971	Remote Similarity	NPD8307	Discontinued
0.596	Remote Similarity	NPD7736	Approved
0.5957	Remote Similarity	NPD6420	Discontinued
0.5956	Remote Similarity	NPD5344	Discontinued
0.5929	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.5922	Remote Similarity	NPD8368	Discontinued
0.5918	Remote Similarity	NPD6059	Approved
0.5915	Remote Similarity	NPD7116	Clinical (unspecified phase)
0.5915	Remote Similarity	NPD2204	Approved
0.5912	Remote Similarity	NPD3653	Clinical (unspecified phase)
0.5912	Remote Similarity	NPD8085	Approved
0.5912	Remote Similarity	NPD8082	Approved
0.5912	Remote Similarity	NPD8084	Approved
0.5912	Remote Similarity	NPD8138	Approved
0.5912	Remote Similarity	NPD8083	Approved
0.5912	Remote Similarity	NPD8086	Approved
0.5912	Remote Similarity	NPD8139	Approved
0.5909	Remote Similarity	NPD5778	Approved
0.5909	Remote Similarity	NPD1446	Phase 3
0.5909	Remote Similarity	NPD5781	Clinical (unspecified phase)
0.5909	Remote Similarity	NPD5779	Approved
0.5909	Remote Similarity	NPD1447	Phase 3
0.5899	Remote Similarity	NPD8393	Approved
0.5894	Remote Similarity	NPD8293	Discontinued
0.5879	Remote Similarity	NPD8389	Clinical (unspecified phase)
0.5878	Remote Similarity	NPD6015	Approved
0.5878	Remote Similarity	NPD6016	Approved
0.587	Remote Similarity	NPD1407	Approved
0.587	Remote Similarity	NPD8435	Approved
0.587	Remote Similarity	NPD8361	Approved
0.587	Remote Similarity	NPD8360	Approved
0.5867	Remote Similarity	NPD7492	Approved
0.5857	Remote Similarity	NPD8140	Approved
0.5845	Remote Similarity	NPD8087	Discontinued
0.5842	Remote Similarity	NPD8486	Clinical (unspecified phase)
0.5839	Remote Similarity	NPD5988	Approved
0.5828	Remote Similarity	NPD6616	Approved
0.5827	Remote Similarity	NPD8081	Approved
0.5809	Remote Similarity	NPD2255	Approved
0.5804	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.5804	Remote Similarity	NPD1719	Phase 1
0.58	Remote Similarity	NPD8328	Phase 3
0.5797	Remote Similarity	NPD7139	Approved
0.5797	Remote Similarity	NPD7140	Approved
0.5797	Remote Similarity	NPD7141	Clinical (unspecified phase)
0.5793	Remote Similarity	NPD7274	Clinical (unspecified phase)
0.5789	Remote Similarity	NPD7078	Approved
0.5775	Remote Similarity	NPD6413	Approved
0.5775	Remote Similarity	NPD8306	Approved
0.5775	Remote Similarity	NPD8305	Approved
0.5775	Remote Similarity	NPD6941	Approved
0.5767	Remote Similarity	NPD8485	Approved
0.5752	Remote Similarity	NPD8336	Approved
0.5752	Remote Similarity	NPD8337	Approved
0.5733	Remote Similarity	NPD7623	Phase 3
0.5733	Remote Similarity	NPD7624	Clinical (unspecified phase)
0.5725	Remote Similarity	NPD618	Clinical (unspecified phase)
0.5723	Remote Similarity	NPD4685	Phase 3
0.5723	Remote Similarity	NPD4684	Phase 3
0.5723	Remote Similarity	NPD4686	Approved
0.5696	Remote Similarity	NPD3616	Approved
0.5696	Remote Similarity	NPD2566	Approved
0.5696	Remote Similarity	NPD2570	Approved
0.5696	Remote Similarity	NPD4745	Approved
0.5696	Remote Similarity	NPD3087	Approved
0.5696	Remote Similarity	NPD2573	Approved
0.5696	Remote Similarity	NPD3089	Approved
0.5696	Remote Similarity	NPD2574	Discontinued
0.5696	Remote Similarity	NPD3615	Approved
0.5696	Remote Similarity	NPD2572	Clinical (unspecified phase)
0.5696	Remote Similarity	NPD3088	Approved
0.5696	Remote Similarity	NPD3614	Approved
0.5696	Remote Similarity	NPD2571	Approved
0.5696	Remote Similarity	NPD3090	Approved
0.5696	Remote Similarity	NPD4746	Phase 3
0.5695	Remote Similarity	NPD7604	Phase 2
0.5676	Remote Similarity	NPD8424	Clinical (unspecified phase)
0.5667	Remote Similarity	NPD8470	Clinical (unspecified phase)
0.5667	Remote Similarity	NPD6909	Approved
0.5667	Remote Similarity	NPD6908	Approved
0.5667	Remote Similarity	NPD7739	Clinical (unspecified phase)
0.5664	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.566	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.566	Remote Similarity	NPD8265	Approved
0.5641	Remote Similarity	NPD7260	Phase 2
0.563	Remote Similarity	NPD5282	Discontinued
0.5625	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.5613	Remote Similarity	NPD7319	Approved
0.5608	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.56	Remote Similarity	NPD6319	Approved
0.56	Remote Similarity	NPD8346	Approved
0.56	Remote Similarity	NPD8347	Approved
0.56	Remote Similarity	NPD8345	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