NPASS Compound

Structure

NPC63041 OpenBabel07101719122D 33 36 0 0 1 0 0 0 0 0999 V2000 0.8426 3.4054 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7156 -0.4782 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8426 2.4324 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4865 -0.8426 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6852 2.9189 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2131 -1.4595 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8426 3.4054 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3705 -0.9730 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6852 1.9459 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4704 0.0503 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7824 0.7383 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2131 -2.4324 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7589 1.2105 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5279 -2.4324 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1664 -0.3102 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 2.9189 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4103 0.3021 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5279 -1.4595 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8426 1.4595 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.7306 1.1596 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8426 1.4595 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8426 0.4865 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.6852 -0.9730 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8426 0.4865 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.0000 1.9459 0.0000 C 0 0 2 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 3.3705 -2.9189 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -5.3429 1.9157 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.6852 1.9459 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8426 -1.4595 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.9730 -1.6852 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.9824 0.2197 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.6852 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 16 1 0 0 0 0 2 24 1 0 0 0 0 5 7 1 0 0 0 0 5 9 1 0 0 0 0 6 8 2 0 0 0 0 6 12 1 0 0 0 0 7 16 2 0 0 0 0 8 18 1 0 0 0 0 9 19 1 0 0 0 0 10 11 2 0 0 0 0 10 17 1 0 0 0 0 11 24 1 0 0 0 0 12 27 2 0 0 0 0 13 17 2 0 0 0 0 13 20 1 0 0 0 0 14 18 2 0 0 0 0 14 27 1 0 0 0 0 15 17 1 0 0 0 0 15 32 1 0 0 0 0 16 25 1 0 0 0 0 18 23 1 0 0 0 0 19 24 1 1 0 0 0 19 25 1 0 0 0 0 20 28 2 0 0 0 0 20 32 1 0 0 0 0 21 22 1 0 0 0 0 21 25 1 1 0 0 0 21 29 1 0 0 0 0 22 26 1 6 0 0 0 22 33 1 0 0 0 0 23 30 2 0 0 0 0 23 33 1 0 0 0 0 24 26 1 6 0 0 0 25 3 1 1 0 0 0 26 4 1 1 0 0 0 26 31 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	453.22
Volume:	466.673
LogP:	2.553
LogD:	1.734
LogS:	-3.698
# Rotatable Bonds:	5
TPSA:	113.02
# H-Bond Aceptor:	7
# H-Bond Donor:	3
# Rings:	4
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.472
Synthetic Accessibility Score:	5.049
Fsp3:	0.462
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:	-5.116
MDCK Permeability:	1.8743410691968165e-05
Pgp-inhibitor:	0.028
Pgp-substrate:	0.323
Human Intestinal Absorption (HIA):	0.09
20% Bioavailability (F20%):	0.602
30% Bioavailability (F30%):	0.463

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.772
Plasma Protein Binding (PPB):	94.34370422363281%
Volume Distribution (VD):	1.807
Pgp-substrate:	9.641390800476074%

ADMET: Metabolism

CYP1A2-inhibitor:	0.532
CYP1A2-substrate:	0.281
CYP2C19-inhibitor:	0.305
CYP2C19-substrate:	0.144
CYP2C9-inhibitor:	0.359
CYP2C9-substrate:	0.889
CYP2D6-inhibitor:	0.667
CYP2D6-substrate:	0.242
CYP3A4-inhibitor:	0.862
CYP3A4-substrate:	0.277

ADMET: Excretion

Clearance (CL):	10.096
Half-life (T1/2):	0.785

ADMET: Toxicity

hERG Blockers:	0.313
Human Hepatotoxicity (H-HT):	0.115
Drug-inuced Liver Injury (DILI):	0.744
AMES Toxicity:	0.004
Rat Oral Acute Toxicity:	0.139
Maximum Recommended Daily Dose:	0.039
Skin Sensitization:	0.657
Carcinogencity:	0.15
Eye Corrosion:	0.003
Eye Irritation:	0.022
Respiratory Toxicity:	0.457

Download Data

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

Natural Product: NPC63041

Natural Product ID:	NPC63041
*Common Name:**	Scutehenanine A
IUPAC Name:	[(1R,2S,3R,4R,4aS,8aR)-1,3-dihydroxy-3,4,8,8a-tetramethyl-4-[(E)-2-(5-oxo-2H-furan-3-yl)ethenyl]-2,4a,5,6-tetrahydro-1H-naphthalen-2-yl] pyridine-3-carboxylate
Synonyms:
Standard InCHIKey:	RWNSVOOPOYYRLS-GLTZHHDWSA-N
Standard InCHI:	InChI=1S/C26H31NO6/c1-16-7-5-9-19-24(2,11-10-17-13-20(28)32-15-17)26(4,31)22(21(29)25(16,19)3)33-23(30)18-8-6-12-27-14-18/h6-8,10-14,19,21-22,29,31H,5,9,15H2,1-4H3/b11-10+/t19-,21+,22+,24-,25+,26+/m1/s1
SMILES:	O=C1OCC(=C1)/C=C/[C@]1(C)[C@H]2CCC=C([C@]2(C)[C@H]([C@@H]([C@]1(C)O)OC(=O)c1cccnc1)O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1078786
PubChem CID:	44556879
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001283] Terpene lactones [CHEMONTID:0001538] Diterpene lactones

*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
NPO16039	Scutellaria barbata	Species	Lamiaceae	Eukaryota	n.a.	whole plant	n.a.	PMID[16755060]
NPO16039	Scutellaria barbata	Species	Lamiaceae	Eukaryota	n.a.	aerial part	n.a.	PMID[17666848]
NPO16039	Scutellaria barbata	Species	Lamiaceae	Eukaryota	n.a.	aerial part	n.a.	PMID[18239311]
NPO16039	Scutellaria barbata	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19785430]
NPO16039	Scutellaria barbata	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19962306]
NPO16039	Scutellaria barbata	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20078074]
NPO16039	Scutellaria barbata	Species	Lamiaceae	Eukaryota	whole plants	Nanning District, Guangxi Province, China	2012-Sep	PMID[25647077]
NPO16039	Scutellaria barbata	Species	Lamiaceae	Eukaryota	aerial parts	Seoul, Korea	n.a.	PMID[26331882]
NPO16039	Scutellaria barbata	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO16039	Scutellaria barbata	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO16039	Scutellaria barbata	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO16039	Scutellaria barbata	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO16039	Scutellaria barbata	Species	Lamiaceae	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
IC50	3

Activity Type	# Activity
Cell Line	2
NON-MOLECULAR	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT91	Cell Line	KB	Homo sapiens	IC50	=	4500.0	nM	PMID[455751]
NPT139	Cell Line	HT-29	Homo sapiens	IC50	=	5800.0	nM	PMID[455751]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	3100.0	nM	PMID[455751]

☑ 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 NPC63041 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	279
0.1-0.2	1260
0.2-0.3	3314
0.3-0.4	10551
0.4-0.5	19172
0.5-0.6	6274
0.6-0.7	1528
0.7-0.8	157
0.8-0.85	51
0.85-0.9	82
0.9-0.95	14
0.95-1	15

Similarity Score	Similarity Level	Natural Product ID
0.9839	High Similarity	NPC472550
0.9839	High Similarity	NPC304179
0.9839	High Similarity	NPC48042
0.9683	High Similarity	NPC472553
0.9634	High Similarity	NPC477910
0.9581	High Similarity	NPC319128
0.9581	High Similarity	NPC228331
0.9531	High Similarity	NPC477907
0.9531	High Similarity	NPC477909
0.9531	High Similarity	NPC42678
0.9482	High Similarity	NPC477908
0.9482	High Similarity	NPC206343
0.9433	High Similarity	NPC62367
0.9385	High Similarity	NPC472555
0.9385	High Similarity	NPC216428
0.9381	High Similarity	NPC475408
0.9381	High Similarity	NPC471014
0.9333	High Similarity	NPC294579
0.9333	High Similarity	NPC144779
0.933	High Similarity	NPC470306
0.9289	High Similarity	NPC477912
0.9282	High Similarity	NPC471016
0.9282	High Similarity	NPC6981
0.9242	High Similarity	NPC477911
0.9188	High Similarity	NPC301368
0.9188	High Similarity	NPC84815
0.915	High Similarity	NPC477902
0.9104	High Similarity	NPC148860
0.91	High Similarity	NPC471980
0.9082	High Similarity	NPC264674
0.9059	High Similarity	NPC124029
0.9055	High Similarity	NPC475137
0.9055	High Similarity	NPC475498
0.9055	High Similarity	NPC473850
0.905	High Similarity	NPC127720
0.905	High Similarity	NPC127026
0.9005	High Similarity	NPC57797
0.9005	High Similarity	NPC250807
0.9005	High Similarity	NPC76565
0.8985	High Similarity	NPC4421
0.8966	High Similarity	NPC211920
0.896	High Similarity	NPC328154
0.8927	High Similarity	NPC477906
0.8922	High Similarity	NPC475362
0.8922	High Similarity	NPC470486
0.8922	High Similarity	NPC471190
0.8922	High Similarity	NPC475644
0.8922	High Similarity	NPC471977
0.8873	High Similarity	NPC476110
0.8873	High Similarity	NPC87152
0.8873	High Similarity	NPC146824
0.8873	High Similarity	NPC228377
0.8873	High Similarity	NPC475600
0.8873	High Similarity	NPC122968
0.8873	High Similarity	NPC477787
0.8873	High Similarity	NPC475601
0.8873	High Similarity	NPC475631
0.8873	High Similarity	NPC328186
0.885	High Similarity	NPC158020
0.885	High Similarity	NPC212768
0.885	High Similarity	NPC473115
0.885	High Similarity	NPC75600
0.885	High Similarity	NPC6576
0.885	High Similarity	NPC473089
0.8835	High Similarity	NPC150698
0.8835	High Similarity	NPC96801
0.8824	High Similarity	NPC473506
0.8812	High Similarity	NPC477903
0.8792	High Similarity	NPC30456
0.8792	High Similarity	NPC469748
0.8768	High Similarity	NPC235364
0.8762	High Similarity	NPC477901
0.875	High Similarity	NPC237702
0.8744	High Similarity	NPC475596
0.8744	High Similarity	NPC473689
0.8744	High Similarity	NPC316841
0.8744	High Similarity	NPC475303
0.8744	High Similarity	NPC292416
0.8718	High Similarity	NPC289086
0.8708	High Similarity	NPC170751
0.8702	High Similarity	NPC244839
0.8702	High Similarity	NPC320324
0.8702	High Similarity	NPC319880
0.8693	High Similarity	NPC476467
0.8683	High Similarity	NPC477900
0.8683	High Similarity	NPC477899
0.8683	High Similarity	NPC26881
0.8676	High Similarity	NPC477788
0.8657	High Similarity	NPC30570
0.8636	High Similarity	NPC472752
0.8619	High Similarity	NPC327769
0.8619	High Similarity	NPC35208
0.8619	High Similarity	NPC475406
0.8619	High Similarity	NPC475426
0.8614	High Similarity	NPC162812
0.86	High Similarity	NPC292517
0.8578	High Similarity	NPC327904
0.8578	High Similarity	NPC38959
0.8517	High Similarity	NPC91125
0.8458	Intermediate Similarity	NPC253482
0.8442	Intermediate Similarity	NPC475835
0.8421	Intermediate Similarity	NPC285411
0.8421	Intermediate Similarity	NPC14116
0.8416	Intermediate Similarity	NPC280473
0.8416	Intermediate Similarity	NPC323551
0.8396	Intermediate Similarity	NPC238278
0.8381	Intermediate Similarity	NPC311196
0.8381	Intermediate Similarity	NPC134384
0.8374	Intermediate Similarity	NPC51008
0.8374	Intermediate Similarity	NPC41724
0.8341	Intermediate Similarity	NPC475648
0.8303	Intermediate Similarity	NPC471013
0.8303	Intermediate Similarity	NPC180668
0.8303	Intermediate Similarity	NPC148896
0.8284	Intermediate Similarity	NPC165837
0.8265	Intermediate Similarity	NPC475533
0.8227	Intermediate Similarity	NPC475315
0.8227	Intermediate Similarity	NPC324619
0.8209	Intermediate Similarity	NPC309498
0.8178	Intermediate Similarity	NPC213143
0.8153	Intermediate Similarity	NPC10904
0.8152	Intermediate Similarity	NPC233727
0.8141	Intermediate Similarity	NPC470279
0.8125	Intermediate Similarity	NPC471015
0.8116	Intermediate Similarity	NPC193361
0.8116	Intermediate Similarity	NPC62844
0.8112	Intermediate Similarity	NPC103230
0.8098	Intermediate Similarity	NPC40919
0.8098	Intermediate Similarity	NPC470189
0.804	Intermediate Similarity	NPC324245
0.804	Intermediate Similarity	NPC320748
0.8039	Intermediate Similarity	NPC470190
0.8038	Intermediate Similarity	NPC187494
0.8009	Intermediate Similarity	NPC475301
0.8009	Intermediate Similarity	NPC85879
0.8009	Intermediate Similarity	NPC53255
0.8009	Intermediate Similarity	NPC326930
0.7974	Intermediate Similarity	NPC13603
0.796	Intermediate Similarity	NPC79223
0.7952	Intermediate Similarity	NPC319556
0.7925	Intermediate Similarity	NPC253314
0.7921	Intermediate Similarity	NPC32451
0.79	Intermediate Similarity	NPC329024
0.7892	Intermediate Similarity	NPC476090
0.7879	Intermediate Similarity	NPC471978
0.787	Intermediate Similarity	NPC473833
0.7857	Intermediate Similarity	NPC207531
0.7833	Intermediate Similarity	NPC328559
0.7824	Intermediate Similarity	NPC317010
0.7802	Intermediate Similarity	NPC328928
0.7772	Intermediate Similarity	NPC317672
0.7772	Intermediate Similarity	NPC59033
0.7729	Intermediate Similarity	NPC156044
0.7717	Intermediate Similarity	NPC107287
0.7702	Intermediate Similarity	NPC471979
0.7641	Intermediate Similarity	NPC471997
0.7638	Intermediate Similarity	NPC44354
0.7633	Intermediate Similarity	NPC12944
0.7633	Intermediate Similarity	NPC25442
0.763	Intermediate Similarity	NPC111732
0.7624	Intermediate Similarity	NPC135950
0.7602	Intermediate Similarity	NPC471004
0.76	Intermediate Similarity	NPC37473
0.7586	Intermediate Similarity	NPC109922
0.7561	Intermediate Similarity	NPC123395
0.7561	Intermediate Similarity	NPC103361
0.7535	Intermediate Similarity	NPC141385
0.7513	Intermediate Similarity	NPC249614
0.75	Intermediate Similarity	NPC112741
0.7488	Intermediate Similarity	NPC155792
0.7437	Intermediate Similarity	NPC207851
0.7394	Intermediate Similarity	NPC263455
0.7387	Intermediate Similarity	NPC327373
0.7371	Intermediate Similarity	NPC314834
0.7327	Intermediate Similarity	NPC325775
0.7327	Intermediate Similarity	NPC328798
0.7323	Intermediate Similarity	NPC164340
0.7317	Intermediate Similarity	NPC289786
0.7297	Intermediate Similarity	NPC167400
0.7282	Intermediate Similarity	NPC146724
0.7241	Intermediate Similarity	NPC107123
0.723	Intermediate Similarity	NPC314297
0.723	Intermediate Similarity	NPC315545
0.7227	Intermediate Similarity	NPC54066
0.7222	Intermediate Similarity	NPC476516
0.722	Intermediate Similarity	NPC114974
0.722	Intermediate Similarity	NPC127647
0.7217	Intermediate Similarity	NPC477043
0.7216	Intermediate Similarity	NPC477975
0.7214	Intermediate Similarity	NPC325093
0.7214	Intermediate Similarity	NPC322043
0.7208	Intermediate Similarity	NPC191310
0.7189	Intermediate Similarity	NPC317752
0.7184	Intermediate Similarity	NPC56170
0.7183	Intermediate Similarity	NPC314855
0.7183	Intermediate Similarity	NPC313345
0.7183	Intermediate Similarity	NPC315638
0.7183	Intermediate Similarity	NPC313796
0.7158	Intermediate Similarity	NPC312860
0.7151	Intermediate Similarity	NPC159630

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 NPC63041 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	190
0.1-0.2	525
0.2-0.3	659
0.3-0.4	1510
0.4-0.5	3458
0.5-0.6	2238
0.6-0.7	543
0.7-0.8	26
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
0.8245	Intermediate Similarity	NPD8304	Clinical (unspecified phase)
0.7937	Intermediate Similarity	NPD8468	Phase 2
0.788	Intermediate Similarity	NPD820	Phase 3
0.7805	Intermediate Similarity	NPD7396	Approved
0.78	Intermediate Similarity	NPD5975	Clinical (unspecified phase)
0.7678	Intermediate Similarity	NPD3794	Approved
0.7678	Intermediate Similarity	NPD3795	Approved
0.7526	Intermediate Similarity	NPD6635	Approved
0.75	Intermediate Similarity	NPD9271	Approved
0.736	Intermediate Similarity	NPD5751	Clinical (unspecified phase)
0.7354	Intermediate Similarity	NPD6026	Approved
0.7346	Intermediate Similarity	NPD7010	Phase 3
0.7345	Intermediate Similarity	NPD5891	Approved
0.7336	Intermediate Similarity	NPD7927	Clinical (unspecified phase)
0.7336	Intermediate Similarity	NPD4417	Approved
0.7333	Intermediate Similarity	NPD485	Clinical (unspecified phase)
0.7306	Intermediate Similarity	NPD3280	Approved
0.7297	Intermediate Similarity	NPD9074	Approved
0.7297	Intermediate Similarity	NPD9075	Approved
0.7286	Intermediate Similarity	NPD5721	Clinical (unspecified phase)
0.7254	Intermediate Similarity	NPD5088	Discontinued
0.7222	Intermediate Similarity	NPD7069	Discontinued
0.7217	Intermediate Similarity	NPD2831	Approved
0.7196	Intermediate Similarity	NPD2510	Approved
0.7196	Intermediate Similarity	NPD2509	Approved
0.7186	Intermediate Similarity	NPD1483	Discontinued
0.7174	Intermediate Similarity	NPD107	Approved
0.7163	Intermediate Similarity	NPD6529	Discontinued
0.7136	Intermediate Similarity	NPD3947	Discontinued
0.7123	Intermediate Similarity	NPD3393	Approved
0.7123	Intermediate Similarity	NPD3394	Approved
0.7123	Intermediate Similarity	NPD3389	Approved
0.7123	Intermediate Similarity	NPD6477	Clinical (unspecified phase)
0.7089	Intermediate Similarity	NPD2121	Clinical (unspecified phase)
0.7053	Intermediate Similarity	NPD2336	Approved
0.7033	Intermediate Similarity	NPD4427	Phase 2
0.7015	Intermediate Similarity	NPD6641	Approved
0.7015	Intermediate Similarity	NPD6642	Approved
0.7014	Intermediate Similarity	NPD8325	Phase 3
0.7014	Intermediate Similarity	NPD8327	Clinical (unspecified phase)
0.7014	Intermediate Similarity	NPD8326	Phase 3
0.7005	Intermediate Similarity	NPD4506	Discontinued
0.7005	Intermediate Similarity	NPD8063	Discontinued
0.699	Remote Similarity	NPD6257	Clinical (unspecified phase)
0.6986	Remote Similarity	NPD6361	Phase 2
0.6977	Remote Similarity	NPD6987	Phase 1
0.6974	Remote Similarity	NPD2511	Approved
0.6957	Remote Similarity	NPD7234	Approved
0.6957	Remote Similarity	NPD7233	Approved
0.6953	Remote Similarity	NPD7885	Phase 2
0.6953	Remote Similarity	NPD7886	Phase 2
0.6948	Remote Similarity	NPD4396	Clinical (unspecified phase)
0.6941	Remote Similarity	NPD5475	Discontinued
0.6938	Remote Similarity	NPD4376	Phase 3
0.6934	Remote Similarity	NPD4987	Clinical (unspecified phase)
0.6919	Remote Similarity	NPD2307	Discontinued
0.6909	Remote Similarity	NPD6657	Clinical (unspecified phase)
0.6905	Remote Similarity	NPD4528	Approved
0.6905	Remote Similarity	NPD4529	Approved
0.6905	Remote Similarity	NPD4526	Approved
0.6893	Remote Similarity	NPD4889	Approved
0.6889	Remote Similarity	NPD4301	Approved
0.6889	Remote Similarity	NPD6298	Discontinued
0.6882	Remote Similarity	NPD2896	Discontinued
0.6875	Remote Similarity	NPD6770	Approved
0.6872	Remote Similarity	NPD2582	Approved
0.6872	Remote Similarity	NPD2581	Approved
0.6866	Remote Similarity	NPD6732	Clinical (unspecified phase)
0.6866	Remote Similarity	NPD4901	Clinical (unspecified phase)
0.6861	Remote Similarity	NPD4989	Phase 2
0.6844	Remote Similarity	NPD8479	Phase 2
0.6835	Remote Similarity	NPD3371	Approved
0.6827	Remote Similarity	NPD6791	Phase 2
0.6826	Remote Similarity	NPD5801	Clinical (unspecified phase)
0.6822	Remote Similarity	NPD6661	Clinical (unspecified phase)
0.6818	Remote Similarity	NPD6262	Clinical (unspecified phase)
0.6818	Remote Similarity	NPD4900	Clinical (unspecified phase)
0.6816	Remote Similarity	NPD5490	Discontinued
0.6789	Remote Similarity	NPD751	Clinical (unspecified phase)
0.6786	Remote Similarity	NPD3326	Clinical (unspecified phase)
0.6777	Remote Similarity	NPD3922	Approved
0.6777	Remote Similarity	NPD3921	Approved
0.6777	Remote Similarity	NPD3924	Approved
0.6777	Remote Similarity	NPD3923	Approved
0.6776	Remote Similarity	NPD7778	Approved
0.6776	Remote Similarity	NPD53	Approved
0.6776	Remote Similarity	NPD7777	Approved
0.6771	Remote Similarity	NPD1270	Approved
0.6761	Remote Similarity	NPD7061	Clinical (unspecified phase)
0.6756	Remote Similarity	NPD7878	Phase 2
0.6753	Remote Similarity	NPD5022	Discontinued
0.675	Remote Similarity	NPD4174	Clinical (unspecified phase)
0.6748	Remote Similarity	NPD7414	Clinical (unspecified phase)
0.6746	Remote Similarity	NPD4948	Discontinued
0.6743	Remote Similarity	NPD5901	Discontinued
0.6743	Remote Similarity	NPD6323	Clinical (unspecified phase)
0.6728	Remote Similarity	NPD7187	Phase 2
0.6725	Remote Similarity	NPD3925	Approved
0.6716	Remote Similarity	NPD5100	Phase 3
0.6712	Remote Similarity	NPD4862	Clinical (unspecified phase)
0.6702	Remote Similarity	NPD3813	Approved
0.6702	Remote Similarity	NPD203	Clinical (unspecified phase)
0.6699	Remote Similarity	NPD4375	Approved
0.6684	Remote Similarity	NPD2809	Approved
0.6682	Remote Similarity	NPD5866	Approved
0.6682	Remote Similarity	NPD6226	Phase 3
0.6682	Remote Similarity	NPD6281	Approved
0.6667	Remote Similarity	NPD1783	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD3386	Phase 2
0.6667	Remote Similarity	NPD3178	Discontinued
0.6667	Remote Similarity	NPD4551	Phase 2
0.6667	Remote Similarity	NPD5147	Discontinued
0.6667	Remote Similarity	NPD1173	Approved
0.6653	Remote Similarity	NPD6525	Clinical (unspecified phase)
0.6652	Remote Similarity	NPD7404	Approved
0.6652	Remote Similarity	NPD7269	Clinical (unspecified phase)
0.665	Remote Similarity	NPD1620	Clinical (unspecified phase)
0.6639	Remote Similarity	NPD6790	Phase 1
0.6637	Remote Similarity	NPD7470	Discontinued
0.6636	Remote Similarity	NPD6219	Discontinued
0.6634	Remote Similarity	NPD6872	Clinical (unspecified phase)
0.6622	Remote Similarity	NPD7707	Approved
0.662	Remote Similarity	NPD6665	Discontinued
0.661	Remote Similarity	NPD3006	Discontinued
0.6609	Remote Similarity	NPD8052	Clinical (unspecified phase)
0.6608	Remote Similarity	NPD7395	Discontinued
0.6608	Remote Similarity	NPD1926	Approved
0.6606	Remote Similarity	NPD7562	Approved
0.6604	Remote Similarity	NPD2544	Clinical (unspecified phase)
0.6604	Remote Similarity	NPD3321	Discontinued
0.6588	Remote Similarity	NPD8020	Approved
0.6588	Remote Similarity	NPD8021	Approved
0.6583	Remote Similarity	NPD5255	Approved
0.6582	Remote Similarity	NPD5965	Clinical (unspecified phase)
0.6582	Remote Similarity	NPD8409	Suspended
0.6581	Remote Similarity	NPD6962	Phase 2
0.6577	Remote Similarity	NPD7947	Clinical (unspecified phase)
0.6574	Remote Similarity	NPD5003	Discontinued
0.6574	Remote Similarity	NPD6206	Phase 1
0.6574	Remote Similarity	NPD8485	Approved
0.6571	Remote Similarity	NPD6241	Phase 1
0.657	Remote Similarity	NPD6276	Discontinued
0.6569	Remote Similarity	NPD1078	Clinical (unspecified phase)
0.6569	Remote Similarity	NPD7417	Discontinued
0.6569	Remote Similarity	NPD6739	Clinical (unspecified phase)
0.6567	Remote Similarity	NPD1631	Approved
0.6565	Remote Similarity	NPD6995	Phase 1
0.6561	Remote Similarity	NPD7001	Phase 3
0.656	Remote Similarity	NPD4601	Approved
0.656	Remote Similarity	NPD4600	Approved
0.656	Remote Similarity	NPD6479	Discontinued
0.6558	Remote Similarity	NPD3395	Approved
0.6558	Remote Similarity	NPD3396	Approved
0.6557	Remote Similarity	NPD4334	Discontinued
0.6557	Remote Similarity	NPD4021	Phase 2
0.6553	Remote Similarity	NPD3238	Discontinued
0.6552	Remote Similarity	NPD7426	Phase 1
0.6552	Remote Similarity	NPD5640	Discontinued
0.6552	Remote Similarity	NPD8289	Discontinued
0.655	Remote Similarity	NPD1996	Discontinued
0.6549	Remote Similarity	NPD5148	Clinical (unspecified phase)
0.6549	Remote Similarity	NPD4897	Phase 2
0.6549	Remote Similarity	NPD5149	Phase 2
0.6547	Remote Similarity	NPD5583	Clinical (unspecified phase)
0.6545	Remote Similarity	NPD5513	Phase 2
0.6545	Remote Similarity	NPD6176	Phase 1
0.6542	Remote Similarity	NPD6569	Phase 2
0.6533	Remote Similarity	NPD3815	Phase 1
0.6533	Remote Similarity	NPD3816	Phase 1
0.6525	Remote Similarity	NPD4373	Phase 2
0.6524	Remote Similarity	NPD1096	Discontinued
0.6524	Remote Similarity	NPD4086	Phase 1
0.6524	Remote Similarity	NPD1627	Clinical (unspecified phase)
0.6522	Remote Similarity	NPD1032	Phase 2
0.6522	Remote Similarity	NPD2753	Discontinued
0.6522	Remote Similarity	NPD5506	Approved
0.6522	Remote Similarity	NPD4923	Phase 1
0.6522	Remote Similarity	NPD5507	Approved
0.6516	Remote Similarity	NPD3946	Clinical (unspecified phase)
0.6516	Remote Similarity	NPD4037	Approved
0.6516	Remote Similarity	NPD4036	Approved
0.6516	Remote Similarity	NPD31	Approved
0.6516	Remote Similarity	NPD4039	Approved
0.6516	Remote Similarity	NPD4122	Approved
0.6516	Remote Similarity	NPD4038	Approved
0.6516	Remote Similarity	NPD4033	Approved
0.6516	Remote Similarity	NPD4034	Approved
0.6516	Remote Similarity	NPD4035	Approved
0.6516	Remote Similarity	NPD32	Approved
0.6514	Remote Similarity	NPD6999	Discontinued
0.6514	Remote Similarity	NPD7000	Clinical (unspecified phase)
0.6513	Remote Similarity	NPD4702	Approved
0.6513	Remote Similarity	NPD5805	Approved
0.6513	Remote Similarity	NPD4703	Approved
0.6506	Remote Similarity	NPD7708	Approved
0.6505	Remote Similarity	NPD5322	Clinical (unspecified phase)
0.6504	Remote Similarity	NPD7571	Clinical (unspecified phase)
0.6502	Remote Similarity	NPD7467	Discontinued
0.6502	Remote Similarity	NPD6446	Discontinued
0.6502	Remote Similarity	NPD7191	Phase 2

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