NPASS Compound

Structure

NPC189237 OpenBabel07101718202D 29 30 0 0 1 0 0 0 0 0999 V2000 -3.0872 1.8625 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3120 0.6378 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -4.0000 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 3.9716 -0.7070 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8376 0.7930 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1305 0.9914 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6730 0.4483 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6390 0.1895 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 -0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9659 -0.2588 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 -3.3461 0.8966 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9716 0.2930 0.0000 C 0 0 0 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 1.7321 -1.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.2395 0.2930 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 3.1055 0.7930 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2971 -0.4757 0.0000 C 0 0 0 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 1.6026 0.7272 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.1055 1.7930 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.2280 -0.8410 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7517 1.7160 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 14 1 0 0 0 0 2 14 1 0 0 0 0 3 15 1 0 0 0 0 4 15 1 0 0 0 0 5 16 1 0 0 0 0 6 16 1 0 0 0 0 8 9 1 0 0 0 0 8 12 1 0 0 0 0 9 14 2 0 0 0 0 10 11 1 0 0 0 0 10 15 2 0 0 0 0 11 17 1 0 0 0 0 12 25 1 0 0 0 0 13 17 1 0 0 0 0 16 21 1 0 0 0 0 17 25 1 1 0 0 0 18 13 1 1 0 0 0 18 22 1 0 0 0 0 18 23 1 0 0 0 0 19 21 1 0 0 0 0 19 22 1 0 0 0 0 19 24 2 0 0 0 0 20 23 1 0 0 0 0 20 24 1 0 0 0 0 20 25 1 1 0 0 0 21 26 2 0 0 0 0 22 27 2 0 0 0 0 23 28 2 0 0 0 0 24 29 1 0 0 0 0 25 7 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	400.26
Volume:	443.185
LogP:	7.074
LogD:	4.115
LogS:	-4.255
# Rotatable Bonds:	7
TPSA:	77.76
# H-Bond Aceptor:	4
# H-Bond Donor:	3
# Rings:	2
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.377
Synthetic Accessibility Score:	4.928
Fsp3:	0.56
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:	-4.831
MDCK Permeability:	1.4552420907421038e-05
Pgp-inhibitor:	0.873
Pgp-substrate:	0.216
Human Intestinal Absorption (HIA):	0.033
20% Bioavailability (F20%):	0.96
30% Bioavailability (F30%):	0.019

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.017
Plasma Protein Binding (PPB):	93.92839813232422%
Volume Distribution (VD):	5.494
Pgp-substrate:	7.49669075012207%

ADMET: Metabolism

CYP1A2-inhibitor:	0.457
CYP1A2-substrate:	0.262
CYP2C19-inhibitor:	0.511
CYP2C19-substrate:	0.624
CYP2C9-inhibitor:	0.733
CYP2C9-substrate:	0.913
CYP2D6-inhibitor:	0.656
CYP2D6-substrate:	0.192
CYP3A4-inhibitor:	0.27
CYP3A4-substrate:	0.228

ADMET: Excretion

Clearance (CL):	14.481
Half-life (T1/2):	0.04

ADMET: Toxicity

hERG Blockers:	0.018
Human Hepatotoxicity (H-HT):	0.866
Drug-inuced Liver Injury (DILI):	0.038
AMES Toxicity:	0.009
Rat Oral Acute Toxicity:	0.286
Maximum Recommended Daily Dose:	0.045
Skin Sensitization:	0.901
Carcinogencity:	0.095
Eye Corrosion:	0.003
Eye Irritation:	0.635
Respiratory Toxicity:	0.888

Download Data

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

Natural Product: NPC189237

Natural Product ID:	NPC189237
*Common Name:**	Hyperatomarin
IUPAC Name:	n.a.
Synonyms:	Hyperatomarin
Standard InCHIKey:	VENDSUCOZZAVBB-QNRRCFITSA-N
Standard InCHI:	InChI=1S/C25H36O4/c1-14(2)9-8-12-25(7)17(11-10-15(3)4)13-18-22(27)19(21(26)16(5)6)24(29)20(25)23(18)28/h9-10,16-18,20,29H,8,11-13H2,1-7H3/t17-,18-,20-,25+/m1/s1
SMILES:	CC(=CCC[C@@]1(C)[C@H](CC=C(C)C)C[C@H]2C(=O)[C@@H]1C(=C(C2=O)C(=O)C(C)C)O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL467830
PubChem CID:	n.a.
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001549] Monoterpenoids [CHEMONTID:0001564] Bicyclic monoterpenoids

*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
NPO33448	hypericumatomarium ssp. degenii	Species	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[14510605]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	NP ID	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
MIC	4

Activity Type	# Activity
Organism	4

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	=	1.56	ug.mL-1	PMID[490167]
NPT729	Organism	Micrococcus luteus	Micrococcus luteus	MIC	=	1.56	ug.mL-1	PMID[490167]
NPT79	Organism	Bacillus subtilis	Bacillus subtilis	MIC	=	3.12	ug.mL-1	PMID[490167]
NPT3598	Organism	Bacillus	Bacillus	MIC	=	3.12	ug.mL-1	PMID[490167]

☑ 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 NPC189237 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	173
0.1-0.2	1290
0.2-0.3	6380
0.3-0.4	14017
0.4-0.5	10674
0.5-0.6	6548
0.6-0.7	2933
0.7-0.8	624
0.8-0.85	47
0.85-0.9	4
0.9-0.95	4
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9481	High Similarity	NPC44963
0.9481	High Similarity	NPC472684
0.859	High Similarity	NPC180886
0.8519	High Similarity	NPC116797
0.8452	Intermediate Similarity	NPC229717
0.8427	Intermediate Similarity	NPC21681
0.8427	Intermediate Similarity	NPC472675
0.8415	Intermediate Similarity	NPC477270
0.8415	Intermediate Similarity	NPC477271
0.8415	Intermediate Similarity	NPC129080
0.8415	Intermediate Similarity	NPC477269
0.8395	Intermediate Similarity	NPC26139
0.8375	Intermediate Similarity	NPC478246
0.8375	Intermediate Similarity	NPC478247
0.8375	Intermediate Similarity	NPC189485
0.8375	Intermediate Similarity	NPC471409
0.8375	Intermediate Similarity	NPC275494
0.8372	Intermediate Similarity	NPC472676
0.8372	Intermediate Similarity	NPC472688
0.8333	Intermediate Similarity	NPC472690
0.8333	Intermediate Similarity	NPC472689
0.8333	Intermediate Similarity	NPC477268
0.8333	Intermediate Similarity	NPC477267
0.8293	Intermediate Similarity	NPC278459
0.8293	Intermediate Similarity	NPC55869
0.8272	Intermediate Similarity	NPC28319
0.8242	Intermediate Similarity	NPC177680
0.8242	Intermediate Similarity	NPC472730
0.8242	Intermediate Similarity	NPC153776
0.8242	Intermediate Similarity	NPC472729
0.8235	Intermediate Similarity	NPC477478
0.8235	Intermediate Similarity	NPC477479
0.8193	Intermediate Similarity	NPC469325
0.8193	Intermediate Similarity	NPC302661
0.8193	Intermediate Similarity	NPC238991
0.8171	Intermediate Similarity	NPC108955
0.8171	Intermediate Similarity	NPC2482
0.8171	Intermediate Similarity	NPC279667
0.8161	Intermediate Similarity	NPC184663
0.8152	Intermediate Similarity	NPC472727
0.8152	Intermediate Similarity	NPC472728
0.8148	Intermediate Similarity	NPC30321
0.8148	Intermediate Similarity	NPC74410
0.814	Intermediate Similarity	NPC38885
0.814	Intermediate Similarity	NPC476409
0.8118	Intermediate Similarity	NPC311702
0.8118	Intermediate Similarity	NPC123319
0.8118	Intermediate Similarity	NPC94531
0.8095	Intermediate Similarity	NPC102197
0.8095	Intermediate Similarity	NPC477373
0.8095	Intermediate Similarity	NPC53733
0.8077	Intermediate Similarity	NPC160817
0.8072	Intermediate Similarity	NPC477372
0.8072	Intermediate Similarity	NPC471898
0.8043	Intermediate Similarity	NPC147954
0.8025	Intermediate Similarity	NPC266193
0.8025	Intermediate Similarity	NPC257666
0.8025	Intermediate Similarity	NPC165711
0.8022	Intermediate Similarity	NPC472734
0.8022	Intermediate Similarity	NPC472733
0.8	Intermediate Similarity	NPC96095
0.7978	Intermediate Similarity	NPC230064
0.7976	Intermediate Similarity	NPC103486
0.7976	Intermediate Similarity	NPC320514
0.7952	Intermediate Similarity	NPC476809
0.7935	Intermediate Similarity	NPC273269
0.7935	Intermediate Similarity	NPC472732
0.7935	Intermediate Similarity	NPC472731
0.7935	Intermediate Similarity	NPC27105
0.7927	Intermediate Similarity	NPC207772
0.7927	Intermediate Similarity	NPC62336
0.7927	Intermediate Similarity	NPC321514
0.7907	Intermediate Similarity	NPC469948
0.7907	Intermediate Similarity	NPC263997
0.7907	Intermediate Similarity	NPC241512
0.7907	Intermediate Similarity	NPC8518
0.7907	Intermediate Similarity	NPC473038
0.7907	Intermediate Similarity	NPC132228
0.7907	Intermediate Similarity	NPC11711
0.7907	Intermediate Similarity	NPC142649
0.7907	Intermediate Similarity	NPC6185
0.7901	Intermediate Similarity	NPC263582
0.7901	Intermediate Similarity	NPC92080
0.7889	Intermediate Similarity	NPC474807
0.7882	Intermediate Similarity	NPC105803
0.7882	Intermediate Similarity	NPC470015
0.7882	Intermediate Similarity	NPC168188
0.7865	Intermediate Similarity	NPC476369
0.7865	Intermediate Similarity	NPC213636
0.7865	Intermediate Similarity	NPC280592
0.7865	Intermediate Similarity	NPC476437
0.7865	Intermediate Similarity	NPC253177
0.7857	Intermediate Similarity	NPC226068
0.7857	Intermediate Similarity	NPC121984
0.7857	Intermediate Similarity	NPC221647
0.7857	Intermediate Similarity	NPC473217
0.7857	Intermediate Similarity	NPC225515
0.7849	Intermediate Similarity	NPC99657
0.7849	Intermediate Similarity	NPC471330
0.7849	Intermediate Similarity	NPC472687
0.7849	Intermediate Similarity	NPC203388
0.7849	Intermediate Similarity	NPC471331
0.7841	Intermediate Similarity	NPC474854
0.7841	Intermediate Similarity	NPC72397
0.7831	Intermediate Similarity	NPC477371
0.7831	Intermediate Similarity	NPC27817
0.7831	Intermediate Similarity	NPC192329
0.7826	Intermediate Similarity	NPC269492
0.7816	Intermediate Similarity	NPC194417
0.7816	Intermediate Similarity	NPC158393
0.7805	Intermediate Similarity	NPC97377
0.7805	Intermediate Similarity	NPC197659
0.7805	Intermediate Similarity	NPC325946
0.7791	Intermediate Similarity	NPC209882
0.7791	Intermediate Similarity	NPC85774
0.7791	Intermediate Similarity	NPC476412
0.7791	Intermediate Similarity	NPC473246
0.7791	Intermediate Similarity	NPC251170
0.7791	Intermediate Similarity	NPC214043
0.7778	Intermediate Similarity	NPC296114
0.7778	Intermediate Similarity	NPC471329
0.7778	Intermediate Similarity	NPC175079
0.7766	Intermediate Similarity	NPC46761
0.7765	Intermediate Similarity	NPC193347
0.7765	Intermediate Similarity	NPC133391
0.7753	Intermediate Similarity	NPC477943
0.7742	Intermediate Similarity	NPC473161
0.7738	Intermediate Similarity	NPC37038
0.7738	Intermediate Similarity	NPC472478
0.7738	Intermediate Similarity	NPC18955
0.7738	Intermediate Similarity	NPC306095
0.7727	Intermediate Similarity	NPC158141
0.7727	Intermediate Similarity	NPC173089
0.7727	Intermediate Similarity	NPC136948
0.7727	Intermediate Similarity	NPC96496
0.7717	Intermediate Similarity	NPC777
0.7711	Intermediate Similarity	NPC476808
0.7711	Intermediate Similarity	NPC280654
0.7711	Intermediate Similarity	NPC110094
0.7711	Intermediate Similarity	NPC179028
0.7711	Intermediate Similarity	NPC178852
0.7711	Intermediate Similarity	NPC260385
0.7701	Intermediate Similarity	NPC476426
0.7701	Intermediate Similarity	NPC29447
0.7701	Intermediate Similarity	NPC474537
0.7701	Intermediate Similarity	NPC474680
0.7692	Intermediate Similarity	NPC131840
0.7683	Intermediate Similarity	NPC1254
0.7683	Intermediate Similarity	NPC472305
0.7683	Intermediate Similarity	NPC470525
0.7683	Intermediate Similarity	NPC186554
0.7683	Intermediate Similarity	NPC76966
0.7683	Intermediate Similarity	NPC151622
0.7683	Intermediate Similarity	NPC7629
0.7674	Intermediate Similarity	NPC258985
0.7674	Intermediate Similarity	NPC49019
0.7674	Intermediate Similarity	NPC64600
0.7674	Intermediate Similarity	NPC97913
0.7654	Intermediate Similarity	NPC251970
0.7654	Intermediate Similarity	NPC241854
0.7654	Intermediate Similarity	NPC476046
0.7647	Intermediate Similarity	NPC267691
0.7647	Intermediate Similarity	NPC162632
0.7647	Intermediate Similarity	NPC201912
0.7647	Intermediate Similarity	NPC147066
0.7647	Intermediate Similarity	NPC263272
0.7647	Intermediate Similarity	NPC3915
0.7647	Intermediate Similarity	NPC274050
0.7647	Intermediate Similarity	NPC327002
0.7647	Intermediate Similarity	NPC38350
0.7647	Intermediate Similarity	NPC90055
0.7647	Intermediate Similarity	NPC14151
0.764	Intermediate Similarity	NPC470524
0.764	Intermediate Similarity	NPC1753
0.764	Intermediate Similarity	NPC474511
0.7634	Intermediate Similarity	NPC473164
0.7625	Intermediate Similarity	NPC84790
0.7619	Intermediate Similarity	NPC327674
0.7619	Intermediate Similarity	NPC231431
0.7619	Intermediate Similarity	NPC308038
0.7619	Intermediate Similarity	NPC199595
0.7619	Intermediate Similarity	NPC215843
0.7619	Intermediate Similarity	NPC472490
0.7614	Intermediate Similarity	NPC470345
0.7614	Intermediate Similarity	NPC118648
0.7614	Intermediate Similarity	NPC327115
0.7614	Intermediate Similarity	NPC470955
0.7614	Intermediate Similarity	NPC475022
0.7614	Intermediate Similarity	NPC475181
0.7614	Intermediate Similarity	NPC262085
0.7614	Intermediate Similarity	NPC474732
0.7614	Intermediate Similarity	NPC474733
0.7614	Intermediate Similarity	NPC6247
0.7614	Intermediate Similarity	NPC31564
0.7614	Intermediate Similarity	NPC474778
0.7614	Intermediate Similarity	NPC222613
0.7614	Intermediate Similarity	NPC145879
0.7609	Intermediate Similarity	NPC114162
0.7609	Intermediate Similarity	NPC469819
0.7604	Intermediate Similarity	NPC163249

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 NPC189237 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	171
0.1-0.2	1781
0.2-0.3	4073
0.3-0.4	2201
0.4-0.5	524
0.5-0.6	223
0.6-0.7	141
0.7-0.8	35
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8171	Intermediate Similarity	NPD4695	Discontinued
0.7816	Intermediate Similarity	NPD3574	Clinical (unspecified phase)
0.7765	Intermediate Similarity	NPD4221	Approved
0.7765	Intermediate Similarity	NPD4223	Phase 3
0.7711	Intermediate Similarity	NPD3617	Approved
0.7701	Intermediate Similarity	NPD5329	Approved
0.7662	Intermediate Similarity	NPD7331	Phase 2
0.7586	Intermediate Similarity	NPD3666	Approved
0.7586	Intermediate Similarity	NPD3665	Phase 1
0.7586	Intermediate Similarity	NPD3133	Approved
0.7586	Intermediate Similarity	NPD4197	Approved
0.7556	Intermediate Similarity	NPD7285	Clinical (unspecified phase)
0.7556	Intermediate Similarity	NPD5328	Approved
0.7447	Intermediate Similarity	NPD7614	Phase 1
0.7416	Intermediate Similarity	NPD4689	Approved
0.7416	Intermediate Similarity	NPD4693	Phase 3
0.7416	Intermediate Similarity	NPD4688	Approved
0.7416	Intermediate Similarity	NPD4519	Discontinued
0.7416	Intermediate Similarity	NPD4138	Approved
0.7416	Intermediate Similarity	NPD4623	Approved
0.7416	Intermediate Similarity	NPD3618	Phase 1
0.7416	Intermediate Similarity	NPD5205	Approved
0.7416	Intermediate Similarity	NPD4690	Approved
0.7416	Intermediate Similarity	NPD4694	Approved
0.7416	Intermediate Similarity	NPD5690	Phase 2
0.7416	Intermediate Similarity	NPD5280	Approved
0.7391	Intermediate Similarity	NPD7515	Phase 2
0.7391	Intermediate Similarity	NPD6079	Approved
0.7386	Intermediate Similarity	NPD4786	Approved
0.7375	Intermediate Similarity	NPD4137	Phase 3
0.7363	Intermediate Similarity	NPD4753	Phase 2
0.7356	Intermediate Similarity	NPD3667	Approved
0.734	Intermediate Similarity	NPD5210	Approved
0.734	Intermediate Similarity	NPD4629	Approved
0.7308	Intermediate Similarity	NPD7341	Phase 2
0.7284	Intermediate Similarity	NPD4691	Approved
0.7284	Intermediate Similarity	NPD4747	Approved
0.7234	Intermediate Similarity	NPD7748	Approved
0.7229	Intermediate Similarity	NPD5733	Approved
0.7222	Intermediate Similarity	NPD5279	Phase 3
0.7204	Intermediate Similarity	NPD5284	Approved
0.7204	Intermediate Similarity	NPD5281	Approved
0.7113	Intermediate Similarity	NPD5696	Approved
0.7083	Intermediate Similarity	NPD5221	Approved
0.7083	Intermediate Similarity	NPD5222	Approved
0.7083	Intermediate Similarity	NPD4697	Phase 3
0.7083	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.7065	Intermediate Similarity	NPD5737	Approved
0.7065	Intermediate Similarity	NPD6672	Approved
0.7033	Intermediate Similarity	NPD7334	Approved
0.7033	Intermediate Similarity	NPD5330	Approved
0.7033	Intermediate Similarity	NPD7521	Approved
0.7033	Intermediate Similarity	NPD6409	Approved
0.7033	Intermediate Similarity	NPD7146	Approved
0.7033	Intermediate Similarity	NPD6684	Approved
0.7024	Intermediate Similarity	NPD4687	Approved
0.7024	Intermediate Similarity	NPD4058	Approved
0.7011	Intermediate Similarity	NPD4195	Approved
0.701	Intermediate Similarity	NPD4755	Approved
0.701	Intermediate Similarity	NPD7902	Approved
0.701	Intermediate Similarity	NPD6083	Phase 2
0.701	Intermediate Similarity	NPD6084	Phase 2
0.701	Intermediate Similarity	NPD5173	Approved
0.7	Intermediate Similarity	NPD3668	Phase 3
0.6989	Remote Similarity	NPD6904	Approved
0.6989	Remote Similarity	NPD6080	Approved
0.6989	Remote Similarity	NPD6673	Approved
0.6988	Remote Similarity	NPD5276	Approved
0.6979	Remote Similarity	NPD5695	Phase 3
0.6957	Remote Similarity	NPD3573	Approved
0.6947	Remote Similarity	NPD6399	Phase 3
0.6947	Remote Similarity	NPD4202	Approved
0.6915	Remote Similarity	NPD4096	Approved
0.6907	Remote Similarity	NPD7732	Phase 3
0.69	Remote Similarity	NPD5091	Approved
0.6889	Remote Similarity	NPD4788	Approved
0.6882	Remote Similarity	NPD6903	Approved
0.6882	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6869	Remote Similarity	NPD4700	Approved
0.6869	Remote Similarity	NPD4696	Approved
0.6869	Remote Similarity	NPD5285	Approved
0.6869	Remote Similarity	NPD5286	Approved
0.6854	Remote Similarity	NPD4692	Approved
0.6854	Remote Similarity	NPD4139	Approved
0.6842	Remote Similarity	NPD6411	Approved
0.6842	Remote Similarity	NPD6050	Approved
0.6835	Remote Similarity	NPD2664	Clinical (unspecified phase)
0.6829	Remote Similarity	NPD3621	Clinical (unspecified phase)
0.68	Remote Similarity	NPD5223	Approved
0.6778	Remote Similarity	NPD4800	Clinical (unspecified phase)
0.6771	Remote Similarity	NPD5133	Approved
0.6753	Remote Similarity	NPD287	Approved
0.6742	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.6737	Remote Similarity	NPD5692	Phase 3
0.6733	Remote Similarity	NPD5226	Approved
0.6733	Remote Similarity	NPD5224	Approved
0.6733	Remote Similarity	NPD5211	Phase 2
0.6733	Remote Similarity	NPD5225	Approved
0.6733	Remote Similarity	NPD4633	Approved
0.6702	Remote Similarity	NPD5208	Approved
0.6702	Remote Similarity	NPD4518	Approved
0.6701	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6701	Remote Similarity	NPD7900	Approved
0.6699	Remote Similarity	NPD6675	Approved
0.6699	Remote Similarity	NPD7128	Approved
0.6699	Remote Similarity	NPD6402	Approved
0.6699	Remote Similarity	NPD5739	Approved
0.6667	Remote Similarity	NPD5175	Approved
0.6667	Remote Similarity	NPD4754	Approved
0.6667	Remote Similarity	NPD5174	Approved
0.6667	Remote Similarity	NPD6098	Approved
0.6667	Remote Similarity	NPD5694	Approved
0.6667	Remote Similarity	NPD5693	Phase 1
0.6633	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6632	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6632	Remote Similarity	NPD6101	Approved
0.6604	Remote Similarity	NPD4634	Approved
0.6602	Remote Similarity	NPD5141	Approved
0.6593	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6588	Remote Similarity	NPD4243	Approved
0.6571	Remote Similarity	NPD7320	Approved
0.6571	Remote Similarity	NPD6899	Approved
0.6571	Remote Similarity	NPD6881	Approved
0.6562	Remote Similarity	NPD5207	Approved
0.6538	Remote Similarity	NPD4767	Approved
0.6538	Remote Similarity	NPD4768	Approved
0.6531	Remote Similarity	NPD5282	Discontinued
0.6509	Remote Similarity	NPD6372	Approved
0.6509	Remote Similarity	NPD6373	Approved
0.6484	Remote Similarity	NPD8028	Phase 2
0.6476	Remote Similarity	NPD6412	Phase 2
0.6476	Remote Similarity	NPD5697	Approved
0.6476	Remote Similarity	NPD5701	Approved
0.6449	Remote Similarity	NPD7290	Approved
0.6449	Remote Similarity	NPD7102	Approved
0.6449	Remote Similarity	NPD6883	Approved
0.6437	Remote Similarity	NPD4784	Approved
0.6437	Remote Similarity	NPD4785	Approved
0.6429	Remote Similarity	NPD5779	Approved
0.6429	Remote Similarity	NPD5778	Approved
0.6415	Remote Similarity	NPD4729	Approved
0.6415	Remote Similarity	NPD6011	Approved
0.6415	Remote Similarity	NPD5128	Approved
0.6415	Remote Similarity	NPD5168	Approved
0.6415	Remote Similarity	NPD4730	Approved
0.6395	Remote Similarity	NPD6081	Approved
0.6392	Remote Similarity	NPD5785	Approved
0.6389	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6389	Remote Similarity	NPD6650	Approved
0.6389	Remote Similarity	NPD8130	Phase 1
0.6389	Remote Similarity	NPD6617	Approved
0.6389	Remote Similarity	NPD6649	Approved
0.6389	Remote Similarity	NPD6869	Approved
0.6389	Remote Similarity	NPD6847	Approved
0.6383	Remote Similarity	NPD5363	Approved
0.6383	Remote Similarity	NPD1696	Phase 3
0.6373	Remote Similarity	NPD6404	Discontinued
0.6364	Remote Similarity	NPD7339	Approved
0.6364	Remote Similarity	NPD6001	Approved
0.6364	Remote Similarity	NPD6942	Approved
0.6355	Remote Similarity	NPD6013	Approved
0.6355	Remote Similarity	NPD6014	Approved
0.6355	Remote Similarity	NPD6012	Approved
0.6344	Remote Similarity	NPD3527	Clinical (unspecified phase)
0.6333	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.633	Remote Similarity	NPD6882	Approved
0.633	Remote Similarity	NPD8297	Approved
0.6321	Remote Similarity	NPD6614	Approved
0.6304	Remote Similarity	NPD5369	Approved
0.63	Remote Similarity	NPD5654	Approved
0.6296	Remote Similarity	NPD5248	Approved
0.6296	Remote Similarity	NPD5247	Approved
0.6296	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.6296	Remote Similarity	NPD5135	Approved
0.6296	Remote Similarity	NPD5250	Approved
0.6296	Remote Similarity	NPD5251	Approved
0.6296	Remote Similarity	NPD5169	Approved
0.6296	Remote Similarity	NPD5249	Phase 3
0.6292	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.6275	Remote Similarity	NPD7638	Approved
0.6264	Remote Similarity	NPD7645	Phase 2
0.625	Remote Similarity	NPD7115	Discovery
0.6239	Remote Similarity	NPD5217	Approved
0.6239	Remote Similarity	NPD5127	Approved
0.6239	Remote Similarity	NPD5215	Approved
0.6239	Remote Similarity	NPD5216	Approved
0.6237	Remote Similarity	NPD4269	Approved
0.6237	Remote Similarity	NPD4270	Approved
0.6228	Remote Similarity	NPD6054	Approved
0.6228	Remote Similarity	NPD6059	Approved
0.6214	Remote Similarity	NPD7639	Approved
0.6214	Remote Similarity	NPD7640	Approved
0.6211	Remote Similarity	NPD1694	Approved
0.6211	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.62	Remote Similarity	NPD5122	Clinical (unspecified phase)
0.6196	Remote Similarity	NPD7525	Registered
0.6196	Remote Similarity	NPD5368	Approved
0.619	Remote Similarity	NPD3704	Approved
0.619	Remote Similarity	NPD6052	Approved
0.619	Remote Similarity	NPD6108	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