NPASS Compound

Structure

NPC209981 OpenBabel07101718242D 28 31 0 0 1 0 0 0 0 0999 V2000 -4.8250 2.2985 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9590 -2.2015 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6948 0.5507 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.8250 1.2985 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2235 -1.6930 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1964 -4.0476 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2269 1.7985 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0929 2.2985 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2269 0.7985 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.8250 -0.7015 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.8250 0.2985 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0057 -2.5640 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1270 -0.4427 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9590 1.7985 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9590 -1.2015 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.9877 -0.1564 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4199 -1.1498 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2531 -1.5981 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9716 -2.8229 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0929 0.2985 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.6787 -2.1158 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4540 -0.8910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9590 0.7985 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.0929 -0.7015 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.1441 -1.1441 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -2.6447 -2.3746 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.2304 -3.7888 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 14 1 0 0 0 0 2 15 1 0 0 0 0 3 16 1 0 0 0 0 6 27 1 0 0 0 0 7 8 1 0 0 0 0 7 9 1 0 0 0 0 8 14 2 0 0 0 0 9 20 1 0 0 0 0 10 11 1 0 0 0 0 10 15 1 0 0 0 0 11 23 1 0 0 0 0 12 18 1 0 0 0 0 12 19 2 0 0 0 0 13 17 1 0 0 0 0 13 24 1 0 0 0 0 14 23 1 0 0 0 0 15 24 1 1 0 0 0 16 25 2 0 0 0 0 16 28 1 0 0 0 0 17 21 2 0 0 0 0 17 22 1 0 0 0 0 18 22 2 0 0 0 0 18 25 1 0 0 0 0 19 21 1 0 0 0 0 19 27 1 0 0 0 0 20 23 1 1 0 0 0 20 24 1 0 0 0 0 21 26 1 0 0 0 0 22 28 1 0 0 0 0 23 4 1 6 0 0 0 24 5 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	383.25
Volume:	413.619
LogP:	5.371
LogD:	4.417
LogS:	-5.15
# Rotatable Bonds:	3
TPSA:	55.49
# H-Bond Aceptor:	4
# H-Bond Donor:	1
# Rings:	4
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.642
Synthetic Accessibility Score:	4.337
Fsp3:	0.625
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.656
MDCK Permeability:	1.8553870177129284e-05
Pgp-inhibitor:	0.958
Pgp-substrate:	0.002
Human Intestinal Absorption (HIA):	0.007
20% Bioavailability (F20%):	0.158
30% Bioavailability (F30%):	0.286

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.378
Plasma Protein Binding (PPB):	94.93516540527344%
Volume Distribution (VD):	2.845
Pgp-substrate:	5.2577900886535645%

ADMET: Metabolism

CYP1A2-inhibitor:	0.414
CYP1A2-substrate:	0.965
CYP2C19-inhibitor:	0.332
CYP2C19-substrate:	0.633
CYP2C9-inhibitor:	0.647
CYP2C9-substrate:	0.74
CYP2D6-inhibitor:	0.536
CYP2D6-substrate:	0.779
CYP3A4-inhibitor:	0.432
CYP3A4-substrate:	0.366

ADMET: Excretion

Clearance (CL):	6.496
Half-life (T1/2):	0.148

ADMET: Toxicity

hERG Blockers:	0.01
Human Hepatotoxicity (H-HT):	0.567
Drug-inuced Liver Injury (DILI):	0.432
AMES Toxicity:	0.026
Rat Oral Acute Toxicity:	0.269
Maximum Recommended Daily Dose:	0.72
Skin Sensitization:	0.875
Carcinogencity:	0.295
Eye Corrosion:	0.004
Eye Irritation:	0.047
Respiratory Toxicity:	0.911

Download Data

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

Natural Product: NPC209981

Natural Product ID:	NPC209981
*Common Name:**	5-Epi-Nakijinol C
IUPAC Name:	7-[[(1R,2S,4aR,8aS)-1,2,4a,5-tetramethyl-2,3,4,7,8,8a-hexahydronaphthalen-1-yl]methyl]-5-methoxy-2-methyl-1,3-benzoxazol-6-ol
Synonyms:
Standard InCHIKey:	ATQVAIUSAHRLDF-KSVBPBMVSA-N
Standard InCHI:	InChI=1S/C24H33NO3/c1-14-8-7-9-20-23(14,4)11-10-15(2)24(20,5)13-17-21(26)19(27-6)12-18-22(17)28-16(3)25-18/h8,12,15,20,26H,7,9-11,13H2,1-6H3/t15-,20+,23-,24+/m0/s1
SMILES:	CC1=CCC[C@@H]2[C@@]1(C)CC[C@H](C)[C@@]2(C)Cc1c(c(cc2c1oc(C)n2)OC)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3109402
PubChem CID:	76335685
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000302] Benzoxazoles

*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
NPO13603	Dactylospongia metachromia	Species	Thorectidae	Eukaryota	n.a.	n.a.	n.a.	PMID[24479418]
NPO13603	Dactylospongia metachromia	Species	Thorectidae	Eukaryota	n.a.	n.a.	n.a.	PMID[33387695]
NPO13603	Dactylospongia metachromia	Species	Thorectidae	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	17

Activity Type	# Activity
Cell Line	1
Individual Protein	16

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1478	Individual Protein	Vascular endothelial growth factor receptor 2	Homo sapiens	IC50	=	3660.0	nM	PMID[475387]
NPT36	Individual Protein	Tyrosine-protein kinase SRC	Homo sapiens	IC50	=	19700.0	nM	PMID[475387]
NPT1656	Individual Protein	Protein kinase N1	Homo sapiens	IC50	>	100000.0	nM	PMID[475387]
NPT1265	Individual Protein	Serine/threonine-protein kinase PIM1	Homo sapiens	IC50	>	100000.0	nM	PMID[475387]
NPT1657	Individual Protein	Serine/threonine-protein kinase NEK6	Homo sapiens	IC50	>	100000.0	nM	PMID[475387]
NPT1658	Individual Protein	Serine/threonine-protein kinase NEK2	Homo sapiens	IC50	>	100000.0	nM	PMID[475387]
NPT1337	Individual Protein	Hepatocyte growth factor receptor	Homo sapiens	IC50	>	100000.0	nM	PMID[475387]
NPT491	Individual Protein	Dual specificity mitogen-activated protein kinase kinase 1	Homo sapiens	IC50	>	100000.0	nM	PMID[475387]
NPT1438	Individual Protein	Insulin-like growth factor I receptor	Homo sapiens	IC50	=	3310.0	nM	PMID[475387]
NPT1436	Individual Protein	Focal adhesion kinase 1	Homo sapiens	IC50	=	7780.0	nM	PMID[475387]
NPT1659	Individual Protein	Tyrosine-protein kinase receptor UFO	Homo sapiens	IC50	=	14700.0	nM	PMID[475387]
NPT1433	Individual Protein	Serine/threonine-protein kinase Aurora-B	Homo sapiens	IC50	>	100000.0	nM	PMID[475387]
NPT1660	Individual Protein	NUAK family SNF1-like kinase 1	Homo sapiens	IC50	>	100000.0	nM	PMID[475387]
NPT1661	Individual Protein	ALK tyrosine kinase receptor	Homo sapiens	IC50	=	3380.0	nM	PMID[475387]
NPT1864	Cell Line	L5178Y	Mus musculus	IC50	>	10000.0	nM	PMID[475387]
NPT831	Individual Protein	Serine/threonine-protein kinase PLK1	Homo sapiens	IC50	>	100000.0	nM	PMID[475387]
NPT728	Individual Protein	Serine/threonine-protein kinase AKT	Homo sapiens	IC50	>	100000.0	nM	PMID[475387]

☑ 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 NPC209981 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	576
0.1-0.2	2321
0.2-0.3	8717
0.3-0.4	9468
0.4-0.5	9077
0.5-0.6	11104
0.6-0.7	1284
0.7-0.8	134
0.8-0.85	12
0.85-0.9	1
0.9-0.95	1
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9283	High Similarity	NPC282346
0.905	High Similarity	NPC470042
0.8238	Intermediate Similarity	NPC72715
0.8065	Intermediate Similarity	NPC203373
0.8054	Intermediate Similarity	NPC101312
0.8031	Intermediate Similarity	NPC230683
0.7863	Intermediate Similarity	NPC160100
0.7812	Intermediate Similarity	NPC185197
0.7765	Intermediate Similarity	NPC120513
0.7729	Intermediate Similarity	NPC58209
0.7649	Intermediate Similarity	NPC188400
0.7608	Intermediate Similarity	NPC302807
0.7581	Intermediate Similarity	NPC34770
0.7568	Intermediate Similarity	NPC129897
0.754	Intermediate Similarity	NPC166712
0.7529	Intermediate Similarity	NPC173250
0.75	Intermediate Similarity	NPC94842
0.75	Intermediate Similarity	NPC314633
0.75	Intermediate Similarity	NPC119134
0.749	Intermediate Similarity	NPC472589
0.749	Intermediate Similarity	NPC1608
0.748	Intermediate Similarity	NPC140296
0.746	Intermediate Similarity	NPC217176
0.7448	Intermediate Similarity	NPC38237
0.7439	Intermediate Similarity	NPC200888
0.7418	Intermediate Similarity	NPC118189
0.7413	Intermediate Similarity	NPC472588
0.7383	Intermediate Similarity	NPC107123
0.7373	Intermediate Similarity	NPC15406
0.7373	Intermediate Similarity	NPC208364
0.7358	Intermediate Similarity	NPC205372
0.7347	Intermediate Similarity	NPC76478
0.7331	Intermediate Similarity	NPC207620
0.7328	Intermediate Similarity	NPC97746
0.7306	Intermediate Similarity	NPC469439
0.7305	Intermediate Similarity	NPC169716
0.7297	Intermediate Similarity	NPC134637
0.7295	Intermediate Similarity	NPC134702
0.7294	Intermediate Similarity	NPC49672
0.7273	Intermediate Similarity	NPC89549
0.7269	Intermediate Similarity	NPC77878
0.7269	Intermediate Similarity	NPC183537
0.7255	Intermediate Similarity	NPC168922
0.7247	Intermediate Similarity	NPC251071
0.7229	Intermediate Similarity	NPC285254
0.7224	Intermediate Similarity	NPC182853
0.7224	Intermediate Similarity	NPC131885
0.7224	Intermediate Similarity	NPC318068
0.7201	Intermediate Similarity	NPC227824
0.7188	Intermediate Similarity	NPC41501
0.7161	Intermediate Similarity	NPC220408
0.7137	Intermediate Similarity	NPC7560
0.7131	Intermediate Similarity	NPC13249
0.7131	Intermediate Similarity	NPC232225
0.7131	Intermediate Similarity	NPC114468
0.7131	Intermediate Similarity	NPC268223
0.7126	Intermediate Similarity	NPC298436
0.7109	Intermediate Similarity	NPC477587
0.7109	Intermediate Similarity	NPC6786
0.7109	Intermediate Similarity	NPC477589
0.7103	Intermediate Similarity	NPC476997
0.7103	Intermediate Similarity	NPC476994
0.7102	Intermediate Similarity	NPC148391
0.7102	Intermediate Similarity	NPC2905
0.7102	Intermediate Similarity	NPC16066
0.7098	Intermediate Similarity	NPC90875
0.709	Intermediate Similarity	NPC203168
0.709	Intermediate Similarity	NPC474428
0.7078	Intermediate Similarity	NPC219664
0.7077	Intermediate Similarity	NPC124313
0.7075	Intermediate Similarity	NPC476998
0.7075	Intermediate Similarity	NPC476996
0.7072	Intermediate Similarity	NPC473188
0.7054	Intermediate Similarity	NPC477588
0.7054	Intermediate Similarity	NPC477590
0.7054	Intermediate Similarity	NPC477586
0.7054	Intermediate Similarity	NPC477585
0.7049	Intermediate Similarity	NPC220241
0.7049	Intermediate Similarity	NPC295479
0.7049	Intermediate Similarity	NPC220337
0.7047	Intermediate Similarity	NPC227033
0.7047	Intermediate Similarity	NPC289905
0.7047	Intermediate Similarity	NPC316065
0.7043	Intermediate Similarity	NPC476995
0.7037	Intermediate Similarity	NPC315634
0.7037	Intermediate Similarity	NPC88923
0.7037	Intermediate Similarity	NPC100734
0.7028	Intermediate Similarity	NPC157983
0.7028	Intermediate Similarity	NPC118154
0.7027	Intermediate Similarity	NPC475844
0.702	Intermediate Similarity	NPC233334
0.7008	Intermediate Similarity	NPC67401
0.7	Intermediate Similarity	NPC207283
0.7	Intermediate Similarity	NPC132385
0.7	Intermediate Similarity	NPC84164
0.6992	Remote Similarity	NPC324361
0.6989	Remote Similarity	NPC215837
0.6988	Remote Similarity	NPC148409
0.6962	Remote Similarity	NPC210296
0.6958	Remote Similarity	NPC161801
0.6952	Remote Similarity	NPC473833
0.6948	Remote Similarity	NPC87560
0.6948	Remote Similarity	NPC195120
0.6941	Remote Similarity	NPC24019
0.6939	Remote Similarity	NPC269367
0.6932	Remote Similarity	NPC270515
0.6929	Remote Similarity	NPC66815
0.6926	Remote Similarity	NPC316292
0.6923	Remote Similarity	NPC474594
0.6914	Remote Similarity	NPC304183
0.6911	Remote Similarity	NPC146418
0.6902	Remote Similarity	NPC315914
0.69	Remote Similarity	NPC471978
0.6893	Remote Similarity	NPC196449
0.6893	Remote Similarity	NPC314222
0.6892	Remote Similarity	NPC54066
0.6889	Remote Similarity	NPC191489
0.6885	Remote Similarity	NPC166722
0.686	Remote Similarity	NPC172222
0.686	Remote Similarity	NPC473182
0.6855	Remote Similarity	NPC30749
0.6852	Remote Similarity	NPC284685
0.685	Remote Similarity	NPC179287
0.685	Remote Similarity	NPC473449
0.6848	Remote Similarity	NPC474688
0.6846	Remote Similarity	NPC189903
0.6846	Remote Similarity	NPC182907
0.6844	Remote Similarity	NPC291609
0.684	Remote Similarity	NPC13603
0.6836	Remote Similarity	NPC274640
0.6825	Remote Similarity	NPC471979
0.6815	Remote Similarity	NPC116178
0.6813	Remote Similarity	NPC184408
0.6812	Remote Similarity	NPC473639
0.6808	Remote Similarity	NPC108342
0.6806	Remote Similarity	NPC124300
0.6803	Remote Similarity	NPC326930
0.6803	Remote Similarity	NPC53255
0.6803	Remote Similarity	NPC475301
0.6803	Remote Similarity	NPC85879
0.6787	Remote Similarity	NPC217903
0.6786	Remote Similarity	NPC172355
0.6783	Remote Similarity	NPC474701
0.6783	Remote Similarity	NPC476999
0.678	Remote Similarity	NPC316224
0.6772	Remote Similarity	NPC210434
0.6772	Remote Similarity	NPC144452
0.6769	Remote Similarity	NPC208898
0.6766	Remote Similarity	NPC471015
0.676	Remote Similarity	NPC146976
0.6759	Remote Similarity	NPC150239
0.6758	Remote Similarity	NPC315499
0.6755	Remote Similarity	NPC180668
0.6755	Remote Similarity	NPC148896
0.6755	Remote Similarity	NPC471013
0.6748	Remote Similarity	NPC212123
0.6748	Remote Similarity	NPC198160
0.6747	Remote Similarity	NPC305542
0.6746	Remote Similarity	NPC473822
0.6745	Remote Similarity	NPC51388
0.6734	Remote Similarity	NPC474366
0.6732	Remote Similarity	NPC280799
0.6731	Remote Similarity	NPC22481
0.673	Remote Similarity	NPC304837
0.673	Remote Similarity	NPC476258
0.6729	Remote Similarity	NPC310618
0.6721	Remote Similarity	NPC90185
0.6721	Remote Similarity	NPC207873
0.6721	Remote Similarity	NPC100573
0.672	Remote Similarity	NPC236668
0.672	Remote Similarity	NPC321166
0.6719	Remote Similarity	NPC208084
0.6707	Remote Similarity	NPC218303
0.6706	Remote Similarity	NPC122463
0.6705	Remote Similarity	NPC246381
0.6704	Remote Similarity	NPC218388
0.6694	Remote Similarity	NPC317572
0.6693	Remote Similarity	NPC225279
0.6693	Remote Similarity	NPC176113
0.6693	Remote Similarity	NPC174760
0.668	Remote Similarity	NPC278525
0.668	Remote Similarity	NPC247803
0.668	Remote Similarity	NPC470482
0.668	Remote Similarity	NPC321428
0.668	Remote Similarity	NPC46561
0.668	Remote Similarity	NPC470481
0.6679	Remote Similarity	NPC478045
0.6667	Remote Similarity	NPC198503
0.6667	Remote Similarity	NPC137929
0.6667	Remote Similarity	NPC329631
0.6667	Remote Similarity	NPC164374
0.6667	Remote Similarity	NPC279589
0.6667	Remote Similarity	NPC280714
0.6655	Remote Similarity	NPC328928
0.6654	Remote Similarity	NPC473183
0.6654	Remote Similarity	NPC10904
0.6654	Remote Similarity	NPC165964
0.6653	Remote Similarity	NPC39500
0.6653	Remote Similarity	NPC469390
0.6653	Remote Similarity	NPC135887

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 NPC209981 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	363
0.1-0.2	630
0.2-0.3	1132
0.3-0.4	2369
0.4-0.5	2719
0.5-0.6	1617
0.6-0.7	307
0.7-0.8	12
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
0.8117	Intermediate Similarity	NPD1505	Phase 2
0.7573	Intermediate Similarity	NPD2433	Clinical (unspecified phase)
0.7336	Intermediate Similarity	NPD2899	Discontinued
0.7297	Intermediate Similarity	NPD6525	Clinical (unspecified phase)
0.7266	Intermediate Similarity	NPD1483	Discontinued
0.7195	Intermediate Similarity	NPD6974	Phase 3
0.7183	Intermediate Similarity	NPD1867	Approved
0.7165	Intermediate Similarity	NPD2951	Discontinued
0.7143	Intermediate Similarity	NPD2779	Approved
0.7093	Intermediate Similarity	NPD7417	Discontinued
0.7088	Intermediate Similarity	NPD7690	Clinical (unspecified phase)
0.7075	Intermediate Similarity	NPD4898	Clinical (unspecified phase)
0.7047	Intermediate Similarity	NPD8067	Phase 3
0.7037	Intermediate Similarity	NPD7803	Approved
0.7033	Intermediate Similarity	NPD4667	Clinical (unspecified phase)
0.7017	Intermediate Similarity	NPD2778	Approved
0.7004	Intermediate Similarity	NPD8461	Discontinued
0.7	Intermediate Similarity	NPD7022	Phase 2
0.6992	Remote Similarity	NPD3945	Discontinued
0.696	Remote Similarity	NPD7180	Phase 3
0.6914	Remote Similarity	NPD1467	Approved
0.6914	Remote Similarity	NPD1466	Phase 3
0.6911	Remote Similarity	NPD4846	Phase 2
0.6889	Remote Similarity	NPD7708	Approved
0.688	Remote Similarity	NPD6503	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD5924	Discontinued
0.687	Remote Similarity	NPD6716	Phase 1
0.6852	Remote Similarity	NPD7956	Approved
0.6852	Remote Similarity	NPD7955	Approved
0.6828	Remote Similarity	NPD5532	Phase 2
0.6824	Remote Similarity	NPD3263	Phase 3
0.6815	Remote Similarity	NPD5866	Approved
0.6811	Remote Similarity	NPD7547	Clinical (unspecified phase)
0.6811	Remote Similarity	NPD7279	Phase 2
0.6811	Remote Similarity	NPD7278	Phase 2
0.6802	Remote Similarity	NPD1166	Clinical (unspecified phase)
0.6801	Remote Similarity	NPD7862	Clinical (unspecified phase)
0.6797	Remote Similarity	NPD7268	Clinical (unspecified phase)
0.6795	Remote Similarity	NPD4373	Phase 2
0.6784	Remote Similarity	NPD6247	Clinical (unspecified phase)
0.6784	Remote Similarity	NPD3925	Approved
0.6757	Remote Similarity	NPD7031	Phase 1
0.6743	Remote Similarity	NPD3250	Phase 1
0.6743	Remote Similarity	NPD7853	Phase 2
0.6729	Remote Similarity	NPD5488	Discontinued
0.6718	Remote Similarity	NPD7048	Phase 3
0.6718	Remote Similarity	NPD4368	Phase 2
0.6706	Remote Similarity	NPD5443	Clinical (unspecified phase)
0.668	Remote Similarity	NPD4952	Phase 3
0.6667	Remote Similarity	NPD7885	Phase 2
0.6667	Remote Similarity	NPD7886	Phase 2
0.6667	Remote Similarity	NPD6741	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD7025	Clinical (unspecified phase)
0.6654	Remote Similarity	NPD7284	Clinical (unspecified phase)
0.6654	Remote Similarity	NPD6962	Phase 2
0.6643	Remote Similarity	NPD6773	Clinical (unspecified phase)
0.6642	Remote Similarity	NPD6252	Clinical (unspecified phase)
0.663	Remote Similarity	NPD8091	Phase 3
0.6629	Remote Similarity	NPD4394	Clinical (unspecified phase)
0.6614	Remote Similarity	NPD5632	Approved
0.6607	Remote Similarity	NPD5922	Phase 3
0.6605	Remote Similarity	NPD5857	Phase 3
0.6603	Remote Similarity	NPD6625	Approved
0.66	Remote Similarity	NPD8279	Clinical (unspecified phase)
0.66	Remote Similarity	NPD2081	Clinical (unspecified phase)
0.6593	Remote Similarity	NPD5482	Discontinued
0.6576	Remote Similarity	NPD6160	Clinical (unspecified phase)
0.6567	Remote Similarity	NPD8357	Approved
0.6564	Remote Similarity	NPD5640	Discontinued
0.6562	Remote Similarity	NPD5850	Phase 3
0.6561	Remote Similarity	NPD1638	Discovery
0.6561	Remote Similarity	NPD5417	Clinical (unspecified phase)
0.6559	Remote Similarity	NPD7597	Clinical (unspecified phase)
0.6544	Remote Similarity	NPD7859	Phase 2
0.6538	Remote Similarity	NPD4328	Approved
0.6532	Remote Similarity	NPD6138	Clinical (unspecified phase)
0.6531	Remote Similarity	NPD6745	Discontinued
0.653	Remote Similarity	NPD6495	Clinical (unspecified phase)
0.6528	Remote Similarity	NPD5805	Approved
0.6525	Remote Similarity	NPD6104	Discontinued
0.6523	Remote Similarity	NPD3258	Approved
0.6517	Remote Similarity	NPD6790	Phase 1
0.6513	Remote Similarity	NPD7710	Clinical (unspecified phase)
0.6513	Remote Similarity	NPD7654	Discontinued
0.651	Remote Similarity	NPD3949	Clinical (unspecified phase)
0.651	Remote Similarity	NPD5164	Discontinued
0.6505	Remote Similarity	NPD1955	Discontinued
0.6496	Remote Similarity	NPD5902	Approved
0.6496	Remote Similarity	NPD5903	Approved
0.6493	Remote Similarity	NPD6517	Phase 3
0.6489	Remote Similarity	NPD5479	Discontinued
0.6484	Remote Similarity	NPD7395	Discontinued
0.6481	Remote Similarity	NPD5817	Discontinued
0.648	Remote Similarity	NPD5429	Discontinued
0.6477	Remote Similarity	NPD6494	Phase 2
0.6471	Remote Similarity	NPD8367	Approved
0.6468	Remote Similarity	NPD3392	Approved
0.646	Remote Similarity	NPD4926	Clinical (unspecified phase)
0.646	Remote Similarity	NPD8463	Approved
0.6449	Remote Similarity	NPD7169	Suspended
0.6448	Remote Similarity	NPD6997	Phase 2
0.6448	Remote Similarity	NPD2285	Clinical (unspecified phase)
0.6444	Remote Similarity	NPD5483	Clinical (unspecified phase)
0.6443	Remote Similarity	NPD5416	Discontinued
0.6443	Remote Similarity	NPD7703	Clinical (unspecified phase)
0.6436	Remote Similarity	NPD8492	Approved
0.6434	Remote Similarity	NPD5930	Phase 3
0.6432	Remote Similarity	NPD1898	Discontinued
0.6426	Remote Similarity	NPD7589	Clinical (unspecified phase)
0.6426	Remote Similarity	NPD5022	Discontinued
0.6414	Remote Similarity	NPD7222	Phase 2
0.6414	Remote Similarity	NPD7452	Approved
0.6414	Remote Similarity	NPD7453	Approved
0.6411	Remote Similarity	NPD7566	Clinical (unspecified phase)
0.6411	Remote Similarity	NPD6321	Discontinued
0.6409	Remote Similarity	NPD7907	Approved
0.6409	Remote Similarity	NPD5507	Approved
0.6409	Remote Similarity	NPD5506	Approved
0.6408	Remote Similarity	NPD5512	Phase 3
0.6406	Remote Similarity	NPD7047	Phase 3
0.6403	Remote Similarity	NPD6530	Approved
0.6403	Remote Similarity	NPD6531	Approved
0.6397	Remote Similarity	NPD3328	Phase 2
0.6397	Remote Similarity	NPD6874	Approved
0.6392	Remote Similarity	NPD7571	Clinical (unspecified phase)
0.6389	Remote Similarity	NPD2916	Discontinued
0.6389	Remote Similarity	NPD6376	Discontinued
0.6385	Remote Similarity	NPD6824	Clinical (unspecified phase)
0.6374	Remote Similarity	NPD7426	Phase 1
0.6371	Remote Similarity	NPD7501	Clinical (unspecified phase)
0.6367	Remote Similarity	NPD8460	Approved
0.6367	Remote Similarity	NPD8459	Approved
0.6367	Remote Similarity	NPD7538	Clinical (unspecified phase)
0.6367	Remote Similarity	NPD3257	Approved
0.6357	Remote Similarity	NPD2921	Clinical (unspecified phase)
0.6351	Remote Similarity	NPD7684	Approved
0.6351	Remote Similarity	NPD7682	Approved
0.635	Remote Similarity	NPD3259	Approved
0.635	Remote Similarity	NPD3809	Discontinued
0.635	Remote Similarity	NPD3986	Discontinued
0.635	Remote Similarity	NPD6475	Phase 2
0.6349	Remote Similarity	NPD7584	Approved
0.6349	Remote Similarity	NPD7263	Phase 2
0.6341	Remote Similarity	NPD8467	Approved
0.6341	Remote Similarity	NPD8465	Approved
0.6341	Remote Similarity	NPD8466	Approved
0.6341	Remote Similarity	NPD8429	Approved
0.6341	Remote Similarity	NPD8427	Approved
0.6341	Remote Similarity	NPD8428	Approved
0.6339	Remote Similarity	NPD5726	Clinical (unspecified phase)
0.6335	Remote Similarity	NPD6456	Discontinued
0.6335	Remote Similarity	NPD4465	Phase 2
0.6335	Remote Similarity	NPD4467	Phase 2
0.6335	Remote Similarity	NPD3946	Clinical (unspecified phase)
0.6332	Remote Similarity	NPD4665	Approved
0.6332	Remote Similarity	NPD2785	Clinical (unspecified phase)
0.6332	Remote Similarity	NPD4111	Phase 1
0.6332	Remote Similarity	NPD3875	Discontinued
0.6331	Remote Similarity	NPD5608	Approved
0.6331	Remote Similarity	NPD5609	Approved
0.633	Remote Similarity	NPD6963	Approved
0.633	Remote Similarity	NPD6964	Approved
0.6324	Remote Similarity	NPD7300	Phase 3
0.6324	Remote Similarity	NPD7302	Phase 3
0.6324	Remote Similarity	NPD6593	Clinical (unspecified phase)
0.6316	Remote Similarity	NPD7490	Discontinued
0.6314	Remote Similarity	NPD8324	Phase 2
0.6314	Remote Similarity	NPD8350	Clinical (unspecified phase)
0.6312	Remote Similarity	NPD5450	Discontinued
0.631	Remote Similarity	NPD3507	Phase 2
0.631	Remote Similarity	NPD3003	Approved
0.6303	Remote Similarity	NPD8363	Approved
0.6303	Remote Similarity	NPD8364	Approved
0.63	Remote Similarity	NPD8359	Phase 2
0.6296	Remote Similarity	NPD4561	Discontinued
0.6293	Remote Similarity	NPD6198	Phase 1
0.6292	Remote Similarity	NPD5040	Clinical (unspecified phase)
0.6292	Remote Similarity	NPD4460	Clinical (unspecified phase)
0.6289	Remote Similarity	NPD7069	Discontinued
0.6288	Remote Similarity	NPD3899	Clinical (unspecified phase)
0.6285	Remote Similarity	NPD7043	Discontinued
0.6285	Remote Similarity	NPD6296	Discontinued
0.6284	Remote Similarity	NPD7556	Discontinued
0.6275	Remote Similarity	NPD6347	Phase 2
0.6268	Remote Similarity	NPD7393	Clinical (unspecified phase)
0.6266	Remote Similarity	NPD5083	Clinical (unspecified phase)
0.626	Remote Similarity	NPD7467	Discontinued
0.626	Remote Similarity	NPD4049	Phase 2
0.626	Remote Similarity	NPD5658	Approved
0.6259	Remote Similarity	NPD8365	Clinical (unspecified phase)
0.6255	Remote Similarity	NPD8102	Discontinued
0.6255	Remote Similarity	NPD8404	Phase 2
0.6255	Remote Similarity	NPD6719	Approved
0.6255	Remote Similarity	NPD7797	Approved
0.6255	Remote Similarity	NPD7796	Approved
0.6255	Remote Similarity	NPD4989	Phase 2
0.6254	Remote Similarity	NPD8426	Approved
0.6254	Remote Similarity	NPD8425	Approved
0.625	Remote Similarity	NPD4605	Approved
0.625	Remote Similarity	NPD8116	Phase 3

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