NPASS Compound

Structure

NPC264819 OpenBabel07101718182D 30 31 0 0 1 0 0 0 0 0999 V2000 0.7765 2.8978 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 0.5000 -1.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0000 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2247 1.2247 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2588 0.9659 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4495 2.4495 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 5.0191 -1.3449 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 6.2438 -0.1201 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4836 2.1907 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2779 -0.3789 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0532 -1.6037 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.1566 1.7424 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5708 0.3282 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3461 -0.8966 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.6049 0.0694 0.0000 C 0 0 1 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 0.0000 0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 6.9509 -0.8272 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.7944 -2.5696 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.1225 2.0012 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.8296 1.2941 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.3801 -1.1554 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.7934 -0.6088 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.8978 0.7765 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 12 1 0 0 0 0 2 13 1 0 0 0 0 3 21 1 0 0 0 0 4 21 1 0 0 0 0 5 6 2 0 0 0 0 5 12 1 0 0 0 0 6 22 1 0 0 0 0 7 12 2 0 0 0 0 7 17 1 0 0 0 0 8 13 2 0 0 0 0 8 15 1 0 0 0 0 9 14 2 0 0 0 0 9 16 1 0 0 0 0 10 15 1 0 0 0 0 10 21 1 0 0 0 0 11 14 1 0 0 0 0 11 23 1 0 0 0 0 13 22 1 0 0 0 0 14 18 1 0 0 0 0 15 24 2 0 0 0 0 16 19 1 0 0 0 0 16 25 1 1 0 0 0 17 26 2 0 0 0 0 17 30 1 0 0 0 0 18 20 1 0 0 0 0 18 27 2 0 0 0 0 19 20 1 0 0 0 0 19 28 1 6 0 0 0 20 30 1 1 0 0 0 21 22 1 0 0 0 0 22 29 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	420.18
Volume:	423.822
LogP:	0.948
LogD:	0.909
LogS:	-2.584
# Rotatable Bonds:	6
TPSA:	138.2
# H-Bond Aceptor:	8
# H-Bond Donor:	3
# Rings:	2
# Heavy Atoms:	8

MedChem Properties

QED Drug-Likeness Score:	0.254
Synthetic Accessibility Score:	4.796
Fsp3:	0.545
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.178
MDCK Permeability:	9.770200267666951e-05
Pgp-inhibitor:	0.031
Pgp-substrate:	0.552
Human Intestinal Absorption (HIA):	0.861
20% Bioavailability (F20%):	0.535
30% Bioavailability (F30%):	0.545

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.694
Plasma Protein Binding (PPB):	71.89020538330078%
Volume Distribution (VD):	0.262
Pgp-substrate:	15.701677322387695%

ADMET: Metabolism

CYP1A2-inhibitor:	0.007
CYP1A2-substrate:	0.116
CYP2C19-inhibitor:	0.056
CYP2C19-substrate:	0.578
CYP2C9-inhibitor:	0.045
CYP2C9-substrate:	0.079
CYP2D6-inhibitor:	0.001
CYP2D6-substrate:	0.061
CYP3A4-inhibitor:	0.08
CYP3A4-substrate:	0.511

ADMET: Excretion

Clearance (CL):	2.501
Half-life (T1/2):	0.778

ADMET: Toxicity

hERG Blockers:	0.027
Human Hepatotoxicity (H-HT):	0.298
Drug-inuced Liver Injury (DILI):	0.401
AMES Toxicity:	0.081
Rat Oral Acute Toxicity:	0.869
Maximum Recommended Daily Dose:	0.944
Skin Sensitization:	0.401
Carcinogencity:	0.66
Eye Corrosion:	0.003
Eye Irritation:	0.011
Respiratory Toxicity:	0.752

Download Data

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

Natural Product: NPC264819

Natural Product ID:	NPC264819
*Common Name:**	Nigrospoxydon A
IUPAC Name:	[(1R,5R,6S)-5,6-dihydroxy-3-(hydroxymethyl)-2-oxocyclohex-3-en-1-yl] (2Z,4E)-5-[(1S)-1-hydroxy-2,6,6-trimethyl-4-oxocyclohex-2-en-1-yl]-3-methylpenta-2,4-dienoate
Synonyms:
Standard InCHIKey:	DMBDZHVALRXOEF-OQNJJOTNSA-N
Standard InCHI:	InChI=1S/C22H28O8/c1-12(5-6-22(29)13(2)8-15(24)10-21(22,3)4)7-17(26)30-20-18(27)14(11-23)9-16(25)19(20)28/h5-9,16,19-20,23,25,28-29H,10-11H2,1-4H3/b6-5+,12-7-/t16-,19+,20+,22-/m1/s1
SMILES:	OCC1=C[C@@H](O)[C@@H]([C@H](C1=O)OC(=O)/C=C(C=C[C@@]1(O)C(=CC(=O)CC1(C)C)C)/C)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL526455
PubChem CID:	25016662
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001550] Sesquiterpenoids [CHEMONTID:0002245] Abscisic acids and derivatives

*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
NPO32983	nigrospora sp. psu-f5	Species	Trichosphaeriaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18646829]

☑ 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	2

Activity Type	# Activity
Organism	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	=	64.0	ug.mL-1	PMID[489180]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	>	128.0	ug.mL-1	PMID[489180]

☑ 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 NPC264819 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	228
0.1-0.2	1206
0.2-0.3	4267
0.3-0.4	7920
0.4-0.5	15438
0.5-0.6	8569
0.6-0.7	4376
0.7-0.8	670
0.8-0.85	17
0.85-0.9	5
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.8762	High Similarity	NPC266514
0.8654	High Similarity	NPC118902
0.8654	High Similarity	NPC469980
0.8654	High Similarity	NPC104161
0.8364	Intermediate Similarity	NPC317687
0.8349	Intermediate Similarity	NPC89408
0.8273	Intermediate Similarity	NPC317107
0.8241	Intermediate Similarity	NPC469853
0.8208	Intermediate Similarity	NPC39996
0.8148	Intermediate Similarity	NPC477125
0.8125	Intermediate Similarity	NPC469454
0.8125	Intermediate Similarity	NPC469463
0.8125	Intermediate Similarity	NPC469496
0.8108	Intermediate Similarity	NPC179798
0.8108	Intermediate Similarity	NPC304180
0.8039	Intermediate Similarity	NPC142838
0.8018	Intermediate Similarity	NPC5103
0.8	Intermediate Similarity	NPC151393
0.8	Intermediate Similarity	NPC322903
0.7965	Intermediate Similarity	NPC56448
0.7965	Intermediate Similarity	NPC471204
0.7928	Intermediate Similarity	NPC87335
0.7925	Intermediate Similarity	NPC61630
0.7925	Intermediate Similarity	NPC307517
0.7925	Intermediate Similarity	NPC81483
0.7925	Intermediate Similarity	NPC169468
0.7899	Intermediate Similarity	NPC24651
0.7899	Intermediate Similarity	NPC470922
0.789	Intermediate Similarity	NPC146731
0.789	Intermediate Similarity	NPC296950
0.7881	Intermediate Similarity	NPC470265
0.7881	Intermediate Similarity	NPC23786
0.7857	Intermediate Similarity	NPC115257
0.7857	Intermediate Similarity	NPC161816
0.7845	Intermediate Similarity	NPC251310
0.7845	Intermediate Similarity	NPC186525
0.783	Intermediate Similarity	NPC474194
0.7826	Intermediate Similarity	NPC64318
0.7826	Intermediate Similarity	NPC270478
0.7818	Intermediate Similarity	NPC469852
0.7815	Intermediate Similarity	NPC67251
0.7798	Intermediate Similarity	NPC473624
0.7798	Intermediate Similarity	NPC472755
0.7798	Intermediate Similarity	NPC159533
0.7797	Intermediate Similarity	NPC67569
0.7797	Intermediate Similarity	NPC472001
0.7778	Intermediate Similarity	NPC207885
0.7778	Intermediate Similarity	NPC268958
0.7778	Intermediate Similarity	NPC112613
0.7768	Intermediate Similarity	NPC475065
0.7768	Intermediate Similarity	NPC42662
0.7768	Intermediate Similarity	NPC475922
0.7759	Intermediate Similarity	NPC27999
0.7759	Intermediate Similarity	NPC477116
0.7759	Intermediate Similarity	NPC23046
0.7757	Intermediate Similarity	NPC159763
0.7757	Intermediate Similarity	NPC316598
0.7757	Intermediate Similarity	NPC124512
0.7757	Intermediate Similarity	NPC278386
0.775	Intermediate Similarity	NPC476729
0.7748	Intermediate Similarity	NPC67321
0.7748	Intermediate Similarity	NPC187435
0.7748	Intermediate Similarity	NPC143609
0.7748	Intermediate Similarity	NPC330011
0.7748	Intermediate Similarity	NPC329048
0.7742	Intermediate Similarity	NPC168879
0.7736	Intermediate Similarity	NPC57664
0.7731	Intermediate Similarity	NPC312833
0.7727	Intermediate Similarity	NPC118911
0.7727	Intermediate Similarity	NPC220964
0.7727	Intermediate Similarity	NPC475676
0.7727	Intermediate Similarity	NPC472756
0.7719	Intermediate Similarity	NPC476801
0.7719	Intermediate Similarity	NPC473877
0.7719	Intermediate Similarity	NPC269530
0.7719	Intermediate Similarity	NPC66108
0.7712	Intermediate Similarity	NPC48692
0.7706	Intermediate Similarity	NPC472754
0.7706	Intermediate Similarity	NPC473596
0.7705	Intermediate Similarity	NPC236999
0.7699	Intermediate Similarity	NPC235014
0.7699	Intermediate Similarity	NPC286880
0.7692	Intermediate Similarity	NPC32552
0.7692	Intermediate Similarity	NPC284707
0.7692	Intermediate Similarity	NPC474286
0.7692	Intermediate Similarity	NPC709
0.7692	Intermediate Similarity	NPC50774
0.7692	Intermediate Similarity	NPC475130
0.7692	Intermediate Similarity	NPC21326
0.7686	Intermediate Similarity	NPC181999
0.7679	Intermediate Similarity	NPC318363
0.7679	Intermediate Similarity	NPC474664
0.7679	Intermediate Similarity	NPC233379
0.7679	Intermediate Similarity	NPC473482
0.7679	Intermediate Similarity	NPC102843
0.7679	Intermediate Similarity	NPC475418
0.7679	Intermediate Similarity	NPC14862
0.7679	Intermediate Similarity	NPC327106
0.7672	Intermediate Similarity	NPC477509
0.7667	Intermediate Similarity	NPC265557
0.7667	Intermediate Similarity	NPC18945
0.7667	Intermediate Similarity	NPC120724
0.7667	Intermediate Similarity	NPC469789
0.7667	Intermediate Similarity	NPC105926
0.7667	Intermediate Similarity	NPC91693
0.7664	Intermediate Similarity	NPC287668
0.7661	Intermediate Similarity	NPC476193
0.7658	Intermediate Similarity	NPC1679
0.7658	Intermediate Similarity	NPC111952
0.7658	Intermediate Similarity	NPC472645
0.7652	Intermediate Similarity	NPC477126
0.7652	Intermediate Similarity	NPC198539
0.7652	Intermediate Similarity	NPC159333
0.7647	Intermediate Similarity	NPC46570
0.7636	Intermediate Similarity	NPC474165
0.7636	Intermediate Similarity	NPC99266
0.7636	Intermediate Similarity	NPC4620
0.7636	Intermediate Similarity	NPC69171
0.7636	Intermediate Similarity	NPC8196
0.7632	Intermediate Similarity	NPC324683
0.7632	Intermediate Similarity	NPC188738
0.7627	Intermediate Similarity	NPC77689
0.7627	Intermediate Similarity	NPC472933
0.7627	Intermediate Similarity	NPC473636
0.7623	Intermediate Similarity	NPC471940
0.7623	Intermediate Similarity	NPC476008
0.7615	Intermediate Similarity	NPC472753
0.7615	Intermediate Similarity	NPC244456
0.7615	Intermediate Similarity	NPC470184
0.7615	Intermediate Similarity	NPC469657
0.7611	Intermediate Similarity	NPC20192
0.7611	Intermediate Similarity	NPC15218
0.7607	Intermediate Similarity	NPC286528
0.7607	Intermediate Similarity	NPC20302
0.7607	Intermediate Similarity	NPC98249
0.7607	Intermediate Similarity	NPC469684
0.7607	Intermediate Similarity	NPC470493
0.7607	Intermediate Similarity	NPC470492
0.7607	Intermediate Similarity	NPC183580
0.7607	Intermediate Similarity	NPC134430
0.7607	Intermediate Similarity	NPC312824
0.7607	Intermediate Similarity	NPC167606
0.7607	Intermediate Similarity	NPC140055
0.7607	Intermediate Similarity	NPC53396
0.7603	Intermediate Similarity	NPC8374
0.7603	Intermediate Similarity	NPC145238
0.7593	Intermediate Similarity	NPC278008
0.7593	Intermediate Similarity	NPC475653
0.7593	Intermediate Similarity	NPC161855
0.7589	Intermediate Similarity	NPC473284
0.7589	Intermediate Similarity	NPC112780
0.7589	Intermediate Similarity	NPC474421
0.7589	Intermediate Similarity	NPC324327
0.7589	Intermediate Similarity	NPC72813
0.7589	Intermediate Similarity	NPC326994
0.7589	Intermediate Similarity	NPC194620
0.7586	Intermediate Similarity	NPC67259
0.7586	Intermediate Similarity	NPC147912
0.7583	Intermediate Similarity	NPC107493
0.757	Intermediate Similarity	NPC255410
0.757	Intermediate Similarity	NPC202833
0.7568	Intermediate Similarity	NPC258532
0.7565	Intermediate Similarity	NPC236217
0.7563	Intermediate Similarity	NPC19336
0.7563	Intermediate Similarity	NPC185876
0.7563	Intermediate Similarity	NPC107338
0.7563	Intermediate Similarity	NPC475885
0.7563	Intermediate Similarity	NPC474370
0.7563	Intermediate Similarity	NPC109607
0.7547	Intermediate Similarity	NPC469491
0.7545	Intermediate Similarity	NPC478176
0.7545	Intermediate Similarity	NPC183571
0.7545	Intermediate Similarity	NPC137430
0.7544	Intermediate Similarity	NPC210005
0.7544	Intermediate Similarity	NPC29133
0.7544	Intermediate Similarity	NPC281624
0.7542	Intermediate Similarity	NPC17772
0.7542	Intermediate Similarity	NPC234522
0.7542	Intermediate Similarity	NPC470776
0.7541	Intermediate Similarity	NPC293112
0.7541	Intermediate Similarity	NPC471939
0.7541	Intermediate Similarity	NPC477745
0.7541	Intermediate Similarity	NPC225049
0.7522	Intermediate Similarity	NPC476802
0.7522	Intermediate Similarity	NPC476479
0.7522	Intermediate Similarity	NPC55972
0.7522	Intermediate Similarity	NPC327286
0.7522	Intermediate Similarity	NPC306265
0.7522	Intermediate Similarity	NPC169888
0.7522	Intermediate Similarity	NPC469916
0.7522	Intermediate Similarity	NPC89171
0.7522	Intermediate Similarity	NPC472439
0.7521	Intermediate Similarity	NPC478216
0.7521	Intermediate Similarity	NPC472399
0.7521	Intermediate Similarity	NPC474333
0.752	Intermediate Similarity	NPC102316
0.75	Intermediate Similarity	NPC470779
0.75	Intermediate Similarity	NPC9303
0.75	Intermediate Similarity	NPC120299
0.75	Intermediate Similarity	NPC472751

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 NPC264819 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	205
0.1-0.2	1548
0.2-0.3	3624
0.3-0.4	2396
0.4-0.5	958
0.5-0.6	337
0.6-0.7	75
0.7-0.8	7
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
0.7757	Intermediate Similarity	NPD4225	Approved
0.7607	Intermediate Similarity	NPD7115	Discovery
0.7417	Intermediate Similarity	NPD6319	Approved
0.729	Intermediate Similarity	NPD5778	Approved
0.729	Intermediate Similarity	NPD5779	Approved
0.7119	Intermediate Similarity	NPD8297	Approved
0.7117	Intermediate Similarity	NPD8029	Clinical (unspecified phase)
0.7094	Intermediate Similarity	NPD6371	Approved
0.7073	Intermediate Similarity	NPD8515	Approved
0.7073	Intermediate Similarity	NPD8513	Phase 3
0.7073	Intermediate Similarity	NPD8516	Approved
0.7073	Intermediate Similarity	NPD8517	Approved
0.7069	Intermediate Similarity	NPD5345	Clinical (unspecified phase)
0.7037	Intermediate Similarity	NPD7983	Approved
0.7034	Intermediate Similarity	NPD6649	Approved
0.7034	Intermediate Similarity	NPD6650	Approved
0.6991	Remote Similarity	NPD5344	Discontinued
0.6983	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6983	Remote Similarity	NPD5697	Approved
0.696	Remote Similarity	NPD8328	Phase 3
0.6944	Remote Similarity	NPD7838	Discovery
0.6944	Remote Similarity	NPD6698	Approved
0.6944	Remote Similarity	NPD46	Approved
0.6923	Remote Similarity	NPD6686	Approved
0.6923	Remote Similarity	NPD6899	Approved
0.6923	Remote Similarity	NPD6881	Approved
0.6917	Remote Similarity	NPD4632	Approved
0.6905	Remote Similarity	NPD7492	Approved
0.6903	Remote Similarity	NPD6648	Approved
0.6881	Remote Similarity	NPD6411	Approved
0.6864	Remote Similarity	NPD6014	Approved
0.6864	Remote Similarity	NPD6013	Approved
0.6864	Remote Similarity	NPD6372	Approved
0.6864	Remote Similarity	NPD6012	Approved
0.6864	Remote Similarity	NPD6373	Approved
0.6864	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6855	Remote Similarity	NPD6054	Approved
0.685	Remote Similarity	NPD6616	Approved
0.6846	Remote Similarity	NPD7260	Phase 2
0.6833	Remote Similarity	NPD6882	Approved
0.6807	Remote Similarity	NPD4634	Approved
0.6807	Remote Similarity	NPD7102	Approved
0.6807	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6807	Remote Similarity	NPD6883	Approved
0.6807	Remote Similarity	NPD7290	Approved
0.68	Remote Similarity	NPD6016	Approved
0.68	Remote Similarity	NPD6015	Approved
0.6797	Remote Similarity	NPD7078	Approved
0.6797	Remote Similarity	NPD8074	Phase 3
0.6796	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.6789	Remote Similarity	NPD5785	Approved
0.678	Remote Similarity	NPD6011	Approved
0.6754	Remote Similarity	NPD7639	Approved
0.6754	Remote Similarity	NPD7640	Approved
0.6752	Remote Similarity	NPD6675	Approved
0.6752	Remote Similarity	NPD7128	Approved
0.6752	Remote Similarity	NPD6402	Approved
0.6752	Remote Similarity	NPD5739	Approved
0.675	Remote Similarity	NPD6847	Approved
0.675	Remote Similarity	NPD6617	Approved
0.675	Remote Similarity	NPD8130	Phase 1
0.675	Remote Similarity	NPD6869	Approved
0.6748	Remote Similarity	NPD6009	Approved
0.6746	Remote Similarity	NPD6370	Approved
0.6746	Remote Similarity	NPD5988	Approved
0.6744	Remote Similarity	NPD7736	Approved
0.6727	Remote Similarity	NPD7637	Suspended
0.6697	Remote Similarity	NPD6101	Approved
0.6697	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6696	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6695	Remote Similarity	NPD5701	Approved
0.6667	Remote Similarity	NPD7638	Approved
0.6667	Remote Similarity	NPD5983	Phase 2
0.6667	Remote Similarity	NPD7503	Approved
0.6639	Remote Similarity	NPD7320	Approved
0.6638	Remote Similarity	NPD5211	Phase 2
0.6636	Remote Similarity	NPD1696	Phase 3
0.6613	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6612	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6607	Remote Similarity	NPD5282	Discontinued
0.6604	Remote Similarity	NPD6110	Phase 1
0.6587	Remote Similarity	NPD6059	Approved
0.6565	Remote Similarity	NPD7319	Approved
0.6562	Remote Similarity	NPD7604	Phase 2
0.6555	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6549	Remote Similarity	NPD5695	Phase 3
0.6538	Remote Similarity	NPD8293	Discontinued
0.6535	Remote Similarity	NPD6921	Approved
0.6525	Remote Similarity	NPD5141	Approved
0.6509	Remote Similarity	NPD5209	Approved
0.6505	Remote Similarity	NPD4756	Discovery
0.6481	Remote Similarity	NPD1694	Approved
0.6466	Remote Similarity	NPD5285	Approved
0.6466	Remote Similarity	NPD4696	Approved
0.6466	Remote Similarity	NPD5286	Approved
0.6462	Remote Similarity	NPD6336	Discontinued
0.6462	Remote Similarity	NPD7507	Approved
0.6446	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6435	Remote Similarity	NPD7902	Approved
0.6435	Remote Similarity	NPD6084	Phase 2
0.6435	Remote Similarity	NPD6083	Phase 2
0.6418	Remote Similarity	NPD6845	Suspended
0.64	Remote Similarity	NPD6274	Approved
0.6379	Remote Similarity	NPD5696	Approved
0.6378	Remote Similarity	NPD7100	Approved
0.6378	Remote Similarity	NPD7101	Approved
0.6356	Remote Similarity	NPD5224	Approved
0.6356	Remote Similarity	NPD5226	Approved
0.6356	Remote Similarity	NPD5225	Approved
0.6356	Remote Similarity	NPD4633	Approved
0.635	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.6349	Remote Similarity	NPD6317	Approved
0.6348	Remote Similarity	NPD7839	Suspended
0.6341	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.633	Remote Similarity	NPD5363	Approved
0.6316	Remote Similarity	NPD7748	Approved
0.6303	Remote Similarity	NPD5174	Approved
0.6303	Remote Similarity	NPD5175	Approved
0.6299	Remote Similarity	NPD7328	Approved
0.6299	Remote Similarity	NPD7327	Approved
0.6299	Remote Similarity	NPD6314	Approved
0.6299	Remote Similarity	NPD6313	Approved
0.6299	Remote Similarity	NPD6335	Approved
0.6293	Remote Similarity	NPD4755	Approved
0.6283	Remote Similarity	NPD7515	Phase 2
0.6283	Remote Similarity	NPD5694	Approved
0.6283	Remote Similarity	NPD5281	Approved
0.6283	Remote Similarity	NPD5284	Approved
0.6279	Remote Similarity	NPD8033	Approved
0.6273	Remote Similarity	NPD5279	Phase 3
0.6271	Remote Similarity	NPD5223	Approved
0.625	Remote Similarity	NPD7516	Approved
0.6239	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.623	Remote Similarity	NPD4730	Approved
0.623	Remote Similarity	NPD4729	Approved
0.6228	Remote Similarity	NPD6399	Phase 3
0.6218	Remote Similarity	NPD7632	Discontinued
0.6207	Remote Similarity	NPD5221	Approved
0.6207	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6207	Remote Similarity	NPD5222	Approved
0.6204	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6202	Remote Similarity	NPD8377	Approved
0.6202	Remote Similarity	NPD8294	Approved
0.6198	Remote Similarity	NPD6008	Approved
0.6195	Remote Similarity	NPD5692	Phase 3
0.6186	Remote Similarity	NPD4700	Approved
0.6183	Remote Similarity	NPD7830	Approved
0.6183	Remote Similarity	NPD7829	Approved
0.6174	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6174	Remote Similarity	NPD7900	Approved
0.616	Remote Similarity	NPD6053	Discontinued
0.6154	Remote Similarity	NPD8380	Approved
0.6154	Remote Similarity	NPD8335	Approved
0.6154	Remote Similarity	NPD8379	Approved
0.6154	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.6154	Remote Similarity	NPD5173	Approved
0.6154	Remote Similarity	NPD8264	Approved
0.6154	Remote Similarity	NPD8378	Approved
0.6154	Remote Similarity	NPD8039	Approved
0.6154	Remote Similarity	NPD8296	Approved
0.6148	Remote Similarity	NPD6412	Phase 2
0.6142	Remote Similarity	NPD6868	Approved
0.614	Remote Similarity	NPD5693	Phase 1
0.614	Remote Similarity	NPD6050	Approved
0.6129	Remote Similarity	NPD5250	Approved
0.6129	Remote Similarity	NPD5247	Approved
0.6129	Remote Similarity	NPD5249	Phase 3
0.6129	Remote Similarity	NPD5248	Approved
0.6129	Remote Similarity	NPD5251	Approved
0.6126	Remote Similarity	NPD3618	Phase 1
0.6121	Remote Similarity	NPD5210	Approved
0.6121	Remote Similarity	NPD4629	Approved
0.6119	Remote Similarity	NPD6033	Approved
0.6106	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6094	Remote Similarity	NPD7500	Approved
0.6071	Remote Similarity	NPD3573	Approved
0.6071	Remote Similarity	NPD7524	Approved
0.6068	Remote Similarity	NPD4697	Phase 3
0.6066	Remote Similarity	NPD4767	Approved
0.6066	Remote Similarity	NPD4768	Approved
0.6061	Remote Similarity	NPD7642	Approved
0.6055	Remote Similarity	NPD4270	Approved
0.6055	Remote Similarity	NPD4269	Approved
0.6031	Remote Similarity	NPD6909	Approved
0.6031	Remote Similarity	NPD6908	Approved
0.6029	Remote Similarity	NPD5956	Approved
0.6019	Remote Similarity	NPD4695	Discontinued
0.6019	Remote Similarity	NPD4252	Approved
0.6019	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6018	Remote Similarity	NPD6672	Approved
0.6018	Remote Similarity	NPD5737	Approved
0.6	Remote Similarity	NPD6079	Approved
0.6	Remote Similarity	NPD4522	Approved
0.5986	Remote Similarity	NPD7236	Approved
0.5984	Remote Similarity	NPD8133	Approved
0.5982	Remote Similarity	NPD5786	Approved
0.5982	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.5982	Remote Similarity	NPD4249	Approved
0.597	Remote Similarity	NPD8273	Phase 1
0.597	Remote Similarity	NPD8451	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