NPASS Compound

Structure

CID310981 OpenBabel06191716122D 32 36 0 0 1 0 0 0 0 0999 V2000 -2.0482 -3.3704 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9936 -3.1665 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0931 0.8926 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6645 1.9762 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3910 0.0004 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5431 -0.4892 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8473 -1.4676 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -1.9568 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3905 2.9365 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8479 1.4686 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5429 2.4475 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.9791 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8716 -1.6856 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2386 1.4685 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8474 0.4892 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4463 -2.4770 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4190 -2.3751 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6951 -0.0008 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.3910 0.9794 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2384 2.4470 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6953 0.0003 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8479 -0.4896 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.6953 0.9794 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8474 -0.4892 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.2697 -0.7922 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.8171 -1.4817 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5432 1.4689 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 -0.7451 1.4623 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.1042 2.9473 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.7898 -1.3798 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.2424 -0.6903 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 16 1 0 0 0 0 2 17 1 0 0 0 0 5 6 1 0 0 0 0 5 19 1 0 0 0 0 7 8 1 0 0 0 0 7 22 1 0 0 0 0 8 24 1 0 0 0 0 9 11 2 0 0 0 0 9 20 1 0 0 0 0 10 12 1 0 0 0 0 10 23 1 0 0 0 0 11 27 1 0 0 0 0 12 28 1 0 0 0 0 13 16 1 0 0 0 0 13 25 1 0 0 0 0 14 19 2 0 0 0 0 14 20 1 0 0 0 0 15 29 2 0 0 0 0 16 17 2 0 0 0 0 17 26 1 0 0 0 0 18 3 1 1 0 0 0 18 22 1 0 0 0 0 19 27 1 0 0 0 0 20 30 2 0 0 0 0 21 6 1 1 0 0 0 21 23 1 0 0 0 0 21 24 1 0 0 0 0 22 28 1 6 0 0 0 23 27 1 6 0 0 0 24 28 1 6 0 0 0 25 18 1 1 0 0 0 25 32 1 0 0 0 0 26 31 2 0 0 0 0 26 32 1 0 0 0 0 27 4 1 6 0 0 0 28 15 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	436.26
Volume:	469.404
LogP:	4.726
LogD:	4.484
LogS:	-4.739
# Rotatable Bonds:	3
TPSA:	60.44
# H-Bond Aceptor:	4
# H-Bond Donor:	0
# Rings:	5
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.339
Synthetic Accessibility Score:	5.104
Fsp3:	0.679
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.786
MDCK Permeability:	2.4946513804025017e-05
Pgp-inhibitor:	0.993
Pgp-substrate:	0.025
Human Intestinal Absorption (HIA):	0.012
20% Bioavailability (F20%):	0.868
30% Bioavailability (F30%):	0.869

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.661
Plasma Protein Binding (PPB):	78.75875091552734%
Volume Distribution (VD):	1.935
Pgp-substrate:	11.834095001220703%

ADMET: Metabolism

CYP1A2-inhibitor:	0.04
CYP1A2-substrate:	0.129
CYP2C19-inhibitor:	0.47
CYP2C19-substrate:	0.55
CYP2C9-inhibitor:	0.468
CYP2C9-substrate:	0.076
CYP2D6-inhibitor:	0.894
CYP2D6-substrate:	0.016
CYP3A4-inhibitor:	0.953
CYP3A4-substrate:	0.82

ADMET: Excretion

Clearance (CL):	11.398
Half-life (T1/2):	0.223

ADMET: Toxicity

hERG Blockers:	0.357
Human Hepatotoxicity (H-HT):	0.45
Drug-inuced Liver Injury (DILI):	0.669
AMES Toxicity:	0.14
Rat Oral Acute Toxicity:	0.767
Maximum Recommended Daily Dose:	0.897
Skin Sensitization:	0.981
Carcinogencity:	0.796
Eye Corrosion:	0.882
Eye Irritation:	0.311
Respiratory Toxicity:	0.981

Download Data

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

Natural Product: NPC310981

Natural Product ID:	NPC310981
*Common Name:**	Paraminabeolide A
IUPAC Name:	(8R,9S,10R,13R,14S,17R)-17-[(1S)-1-[(2R)-4,5-dimethyl-6-oxo-2,3-dihydropyran-2-yl]ethyl]-10-methyl-3-oxo-6,7,8,9,11,12,14,15,16,17-decahydrocyclopenta[a]phenanthrene-13-carbaldehyde
Synonyms:	Paraminabeolide A
Standard InCHIKey:	TXZGYZBGLCFIQO-JFDBTBFLSA-N
Standard InCHI:	InChI=1S/C28H36O4/c1-16-13-25(32-26(31)17(16)2)18(3)22-7-8-24-21-6-5-19-14-20(30)9-11-27(19,4)23(21)10-12-28(22,24)15-29/h9,11,14-15,18,21-25H,5-8,10,12-13H2,1-4H3/t18-,21+,22+,23-,24-,25+,27-,28-/m0/s1
SMILES:	O=C[C@]12CC[C@H]3[C@H]([C@@H]1CC[C@@H]2[C@@H]([C@H]1CC(=C(C(=O)O1)C)C)C)CCC1=CC(=O)C=C[C@]31C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1782222
PubChem CID:	53262728
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0001125] Steroid lactones [CHEMONTID:0001560] Withanolides 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
NPO27202	Paraminabea acronocephala	Species	Alcyoniidae	Eukaryota	n.a.	the western coast of Pingtung county, Taiwan, at a depth of 10 m	2009-MAY	PMID[21425785]
NPO27202	Paraminabea acronocephala	Species	Alcyoniidae	Eukaryota	n.a.	n.a.	n.a.	PMID[21425785]
NPO27202	Paraminabea acronocephala	Species	Alcyoniidae	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	1
Others	2

Activity Type	# Activity
Cell Line	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT65	Cell Line	HepG2	Homo sapiens	IC50	=	8000.0	nM	PMID[491195]
NPT113	Cell Line	RAW264.7	Mus musculus	Inhibition	=	11.0	%	PMID[491195]
NPT113	Cell Line	RAW264.7	Mus musculus	Inhibition	=	66.5	%	PMID[491195]

☑ 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 NPC310981 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	233
0.1-0.2	1217
0.2-0.3	4514
0.3-0.4	10269
0.4-0.5	11683
0.5-0.6	7202
0.6-0.7	5634
0.7-0.8	1796
0.8-0.85	128
0.85-0.9	19
0.9-0.95	1
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9053	High Similarity	NPC33473
0.9032	High Similarity	NPC273199
0.8936	High Similarity	NPC218301
0.8925	High Similarity	NPC177141
0.8854	High Similarity	NPC281134
0.8776	High Similarity	NPC98868
0.8763	High Similarity	NPC111684
0.8763	High Similarity	NPC58052
0.8725	High Similarity	NPC475294
0.8713	High Similarity	NPC189616
0.8654	High Similarity	NPC37116
0.8654	High Similarity	NPC473627
0.8614	High Similarity	NPC470954
0.8602	High Similarity	NPC220478
0.8586	High Similarity	NPC176845
0.8544	High Similarity	NPC91034
0.8526	High Similarity	NPC474844
0.8485	Intermediate Similarity	NPC84335
0.8485	Intermediate Similarity	NPC38530
0.8462	Intermediate Similarity	NPC177064
0.8454	Intermediate Similarity	NPC79117
0.8454	Intermediate Similarity	NPC229976
0.8447	Intermediate Similarity	NPC470267
0.8438	Intermediate Similarity	NPC101651
0.8438	Intermediate Similarity	NPC159748
0.8416	Intermediate Similarity	NPC168319
0.8416	Intermediate Similarity	NPC194028
0.8396	Intermediate Similarity	NPC474315
0.8396	Intermediate Similarity	NPC470960
0.8367	Intermediate Similarity	NPC294266
0.8365	Intermediate Similarity	NPC476958
0.8351	Intermediate Similarity	NPC190442
0.8333	Intermediate Similarity	NPC271266
0.8333	Intermediate Similarity	NPC474181
0.8333	Intermediate Similarity	NPC475320
0.8333	Intermediate Similarity	NPC284561
0.8333	Intermediate Similarity	NPC308351
0.8318	Intermediate Similarity	NPC475524
0.8318	Intermediate Similarity	NPC100267
0.8317	Intermediate Similarity	NPC470906
0.83	Intermediate Similarity	NPC202705
0.83	Intermediate Similarity	NPC292133
0.83	Intermediate Similarity	NPC110937
0.8298	Intermediate Similarity	NPC189311
0.8286	Intermediate Similarity	NPC220155
0.8283	Intermediate Similarity	NPC274417
0.828	Intermediate Similarity	NPC470047
0.828	Intermediate Similarity	NPC470046
0.8269	Intermediate Similarity	NPC189863
0.8257	Intermediate Similarity	NPC190286
0.8252	Intermediate Similarity	NPC254202
0.8247	Intermediate Similarity	NPC212679
0.8247	Intermediate Similarity	NPC469595
0.8247	Intermediate Similarity	NPC328141
0.8247	Intermediate Similarity	NPC220454
0.8241	Intermediate Similarity	NPC122056
0.8241	Intermediate Similarity	NPC73050
0.8235	Intermediate Similarity	NPC476223
0.8235	Intermediate Similarity	NPC224720
0.8235	Intermediate Similarity	NPC474327
0.8235	Intermediate Similarity	NPC476240
0.8218	Intermediate Similarity	NPC197386
0.8218	Intermediate Similarity	NPC252295
0.8211	Intermediate Similarity	NPC264127
0.8211	Intermediate Similarity	NPC470051
0.8211	Intermediate Similarity	NPC470050
0.8211	Intermediate Similarity	NPC195640
0.82	Intermediate Similarity	NPC328371
0.8198	Intermediate Similarity	NPC475520
0.8182	Intermediate Similarity	NPC269729
0.8173	Intermediate Similarity	NPC235889
0.8173	Intermediate Similarity	NPC472868
0.8172	Intermediate Similarity	NPC100297
0.8165	Intermediate Similarity	NPC67259
0.8165	Intermediate Similarity	NPC147912
0.8155	Intermediate Similarity	NPC136289
0.8148	Intermediate Similarity	NPC191620
0.8148	Intermediate Similarity	NPC236217
0.8148	Intermediate Similarity	NPC221144
0.8148	Intermediate Similarity	NPC69291
0.8144	Intermediate Similarity	NPC285982
0.8144	Intermediate Similarity	NPC469546
0.8137	Intermediate Similarity	NPC476274
0.8131	Intermediate Similarity	NPC29133
0.8125	Intermediate Similarity	NPC477228
0.8119	Intermediate Similarity	NPC253826
0.8119	Intermediate Similarity	NPC151488
0.8119	Intermediate Similarity	NPC2049
0.8119	Intermediate Similarity	NPC476768
0.8119	Intermediate Similarity	NPC226986
0.8119	Intermediate Similarity	NPC23680
0.8108	Intermediate Similarity	NPC153440
0.8105	Intermediate Similarity	NPC137493
0.8105	Intermediate Similarity	NPC323765
0.8105	Intermediate Similarity	NPC2709
0.81	Intermediate Similarity	NPC174948
0.81	Intermediate Similarity	NPC171395
0.81	Intermediate Similarity	NPC173875
0.81	Intermediate Similarity	NPC469995
0.81	Intermediate Similarity	NPC318282
0.81	Intermediate Similarity	NPC293052
0.8095	Intermediate Similarity	NPC266570
0.8095	Intermediate Similarity	NPC60681
0.8095	Intermediate Similarity	NPC181265
0.8095	Intermediate Similarity	NPC127790
0.8091	Intermediate Similarity	NPC148458
0.8091	Intermediate Similarity	NPC176840
0.8085	Intermediate Similarity	NPC193198
0.8081	Intermediate Similarity	NPC474185
0.8077	Intermediate Similarity	NPC176883
0.8061	Intermediate Similarity	NPC152467
0.8061	Intermediate Similarity	NPC475965
0.8061	Intermediate Similarity	NPC474842
0.8061	Intermediate Similarity	NPC469372
0.8058	Intermediate Similarity	NPC99411
0.8058	Intermediate Similarity	NPC81530
0.8056	Intermediate Similarity	NPC470961
0.8041	Intermediate Similarity	NPC472220
0.8041	Intermediate Similarity	NPC97884
0.8041	Intermediate Similarity	NPC215831
0.8041	Intermediate Similarity	NPC226863
0.8039	Intermediate Similarity	NPC57079
0.8039	Intermediate Similarity	NPC108368
0.8039	Intermediate Similarity	NPC114274
0.8036	Intermediate Similarity	NPC5292
0.8021	Intermediate Similarity	NPC168248
0.802	Intermediate Similarity	NPC106425
0.802	Intermediate Similarity	NPC471039
0.802	Intermediate Similarity	NPC122324
0.802	Intermediate Similarity	NPC322063
0.802	Intermediate Similarity	NPC307164
0.802	Intermediate Similarity	NPC151725
0.8018	Intermediate Similarity	NPC476965
0.8018	Intermediate Similarity	NPC286528
0.8018	Intermediate Similarity	NPC20302
0.8018	Intermediate Similarity	NPC167606
0.8018	Intermediate Similarity	NPC239273
0.8018	Intermediate Similarity	NPC140055
0.8018	Intermediate Similarity	NPC470959
0.8	Intermediate Similarity	NPC164835
0.8	Intermediate Similarity	NPC120351
0.8	Intermediate Similarity	NPC228669
0.8	Intermediate Similarity	NPC184870
0.8	Intermediate Similarity	NPC109512
0.8	Intermediate Similarity	NPC166143
0.8	Intermediate Similarity	NPC476415
0.8	Intermediate Similarity	NPC471040
0.8	Intermediate Similarity	NPC471994
0.8	Intermediate Similarity	NPC477129
0.8	Intermediate Similarity	NPC470297
0.8	Intermediate Similarity	NPC477130
0.8	Intermediate Similarity	NPC255309
0.7982	Intermediate Similarity	NPC264634
0.7982	Intermediate Similarity	NPC170538
0.7981	Intermediate Similarity	NPC185530
0.7981	Intermediate Similarity	NPC114540
0.7981	Intermediate Similarity	NPC155332
0.7981	Intermediate Similarity	NPC32577
0.798	Intermediate Similarity	NPC221282
0.7979	Intermediate Similarity	NPC327969
0.7979	Intermediate Similarity	NPC200513
0.7979	Intermediate Similarity	NPC321289
0.7965	Intermediate Similarity	NPC79579
0.7965	Intermediate Similarity	NPC474585
0.7963	Intermediate Similarity	NPC16270
0.7963	Intermediate Similarity	NPC470496
0.7963	Intermediate Similarity	NPC197428
0.7961	Intermediate Similarity	NPC201406
0.7961	Intermediate Similarity	NPC475202
0.7961	Intermediate Similarity	NPC287833
0.7961	Intermediate Similarity	NPC475385
0.7961	Intermediate Similarity	NPC475392
0.7959	Intermediate Similarity	NPC5509
0.7959	Intermediate Similarity	NPC262043
0.7959	Intermediate Similarity	NPC73995
0.7946	Intermediate Similarity	NPC311554
0.7946	Intermediate Similarity	NPC473720
0.7946	Intermediate Similarity	NPC257457
0.7946	Intermediate Similarity	NPC50774
0.7946	Intermediate Similarity	NPC709
0.7944	Intermediate Similarity	NPC275539
0.7944	Intermediate Similarity	NPC470269
0.7944	Intermediate Similarity	NPC189075
0.7944	Intermediate Similarity	NPC61411
0.7941	Intermediate Similarity	NPC257726
0.7941	Intermediate Similarity	NPC126815
0.7941	Intermediate Similarity	NPC291634
0.7941	Intermediate Similarity	NPC108078
0.7941	Intermediate Similarity	NPC474343
0.7941	Intermediate Similarity	NPC204054
0.7938	Intermediate Similarity	NPC163016
0.7938	Intermediate Similarity	NPC75315
0.7925	Intermediate Similarity	NPC96377
0.7921	Intermediate Similarity	NPC476174
0.7921	Intermediate Similarity	NPC280877
0.7921	Intermediate Similarity	NPC470016
0.7921	Intermediate Similarity	NPC317586
0.7921	Intermediate Similarity	NPC470978
0.7921	Intermediate Similarity	NPC470974
0.7921	Intermediate Similarity	NPC469599

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 NPC310981 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	192
0.1-0.2	1403
0.2-0.3	3741
0.3-0.4	2497
0.4-0.5	823
0.5-0.6	211
0.6-0.7	163
0.7-0.8	110
0.8-0.85	10
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8229	Intermediate Similarity	NPD6672	Approved
0.8229	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.8229	Intermediate Similarity	NPD5737	Approved
0.8211	Intermediate Similarity	NPD5330	Approved
0.8211	Intermediate Similarity	NPD7334	Approved
0.8211	Intermediate Similarity	NPD7146	Approved
0.8211	Intermediate Similarity	NPD6684	Approved
0.8211	Intermediate Similarity	NPD7521	Approved
0.8211	Intermediate Similarity	NPD6409	Approved
0.8041	Intermediate Similarity	NPD6903	Approved
0.8018	Intermediate Similarity	NPD7115	Discovery
0.798	Intermediate Similarity	NPD5693	Phase 1
0.7979	Intermediate Similarity	NPD4752	Clinical (unspecified phase)
0.79	Intermediate Similarity	NPD6399	Phase 3
0.78	Intermediate Similarity	NPD6079	Approved
0.7778	Intermediate Similarity	NPD6080	Approved
0.7778	Intermediate Similarity	NPD6881	Approved
0.7778	Intermediate Similarity	NPD6904	Approved
0.7778	Intermediate Similarity	NPD6673	Approved
0.7778	Intermediate Similarity	NPD6899	Approved
0.7755	Intermediate Similarity	NPD3573	Approved
0.7732	Intermediate Similarity	NPD1694	Approved
0.7685	Intermediate Similarity	NPD5697	Approved
0.7636	Intermediate Similarity	NPD7102	Approved
0.7636	Intermediate Similarity	NPD6883	Approved
0.7636	Intermediate Similarity	NPD7290	Approved
0.7615	Intermediate Similarity	NPD6011	Approved
0.76	Intermediate Similarity	NPD6051	Approved
0.76	Intermediate Similarity	NPD5328	Approved
0.7596	Intermediate Similarity	NPD6083	Phase 2
0.7596	Intermediate Similarity	NPD6084	Phase 2
0.7593	Intermediate Similarity	NPD6008	Approved
0.7593	Intermediate Similarity	NPD5739	Approved
0.7593	Intermediate Similarity	NPD6675	Approved
0.7593	Intermediate Similarity	NPD7128	Approved
0.7593	Intermediate Similarity	NPD6402	Approved
0.7573	Intermediate Similarity	NPD6356	Clinical (unspecified phase)
0.7568	Intermediate Similarity	NPD6869	Approved
0.7568	Intermediate Similarity	NPD6649	Approved
0.7568	Intermediate Similarity	NPD6847	Approved
0.7568	Intermediate Similarity	NPD8130	Phase 1
0.7568	Intermediate Similarity	NPD6617	Approved
0.7568	Intermediate Similarity	NPD6650	Approved
0.7545	Intermediate Similarity	NPD6012	Approved
0.7545	Intermediate Similarity	NPD6014	Approved
0.7545	Intermediate Similarity	NPD6013	Approved
0.7524	Intermediate Similarity	NPD7638	Approved
0.75	Intermediate Similarity	NPD5208	Approved
0.75	Intermediate Similarity	NPD6882	Approved
0.75	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD4697	Phase 3
0.75	Intermediate Similarity	NPD8297	Approved
0.75	Intermediate Similarity	NPD5222	Approved
0.75	Intermediate Similarity	NPD5221	Approved
0.7476	Intermediate Similarity	NPD7748	Approved
0.7476	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.7476	Intermediate Similarity	NPD7900	Approved
0.7475	Intermediate Similarity	NPD6098	Approved
0.7455	Intermediate Similarity	NPD7320	Approved
0.7453	Intermediate Similarity	NPD7639	Approved
0.7453	Intermediate Similarity	NPD7640	Approved
0.7451	Intermediate Similarity	NPD6050	Approved
0.7451	Intermediate Similarity	NPD5694	Approved
0.7449	Intermediate Similarity	NPD4786	Approved
0.7429	Intermediate Similarity	NPD5173	Approved
0.7404	Intermediate Similarity	NPD5695	Phase 3
0.7387	Intermediate Similarity	NPD6373	Approved
0.7387	Intermediate Similarity	NPD6372	Approved
0.7364	Intermediate Similarity	NPD5701	Approved
0.7358	Intermediate Similarity	NPD5696	Approved
0.7353	Intermediate Similarity	NPD5207	Approved
0.7353	Intermediate Similarity	NPD5692	Phase 3
0.7345	Intermediate Similarity	NPD6053	Discontinued
0.7315	Intermediate Similarity	NPD5211	Phase 2
0.7304	Intermediate Similarity	NPD6868	Approved
0.729	Intermediate Similarity	NPD5286	Approved
0.729	Intermediate Similarity	NPD4696	Approved
0.729	Intermediate Similarity	NPD5285	Approved
0.7282	Intermediate Similarity	NPD7515	Phase 2
0.7273	Intermediate Similarity	NPD3666	Approved
0.7273	Intermediate Similarity	NPD3133	Approved
0.7273	Intermediate Similarity	NPD3665	Phase 1
0.7273	Intermediate Similarity	NPD3668	Phase 3
0.7264	Intermediate Similarity	NPD7902	Approved
0.7257	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.7245	Intermediate Similarity	NPD3667	Approved
0.7222	Intermediate Similarity	NPD5223	Approved
0.719	Intermediate Similarity	NPD7507	Approved
0.7184	Intermediate Similarity	NPD5785	Approved
0.7182	Intermediate Similarity	NPD5141	Approved
0.7179	Intermediate Similarity	NPD6335	Approved
0.7156	Intermediate Similarity	NPD5225	Approved
0.7156	Intermediate Similarity	NPD5224	Approved
0.7156	Intermediate Similarity	NPD4633	Approved
0.7156	Intermediate Similarity	NPD5226	Approved
0.7143	Intermediate Similarity	NPD6001	Approved
0.713	Intermediate Similarity	NPD4632	Approved
0.7129	Intermediate Similarity	NPD3618	Phase 1
0.7119	Intermediate Similarity	NPD7100	Approved
0.7119	Intermediate Similarity	NPD7101	Approved
0.7115	Intermediate Similarity	NPD5284	Approved
0.7115	Intermediate Similarity	NPD5281	Approved
0.7103	Intermediate Similarity	NPD4755	Approved
0.7094	Intermediate Similarity	NPD6317	Approved
0.7091	Intermediate Similarity	NPD5174	Approved
0.7091	Intermediate Similarity	NPD5175	Approved
0.7087	Intermediate Similarity	NPD4753	Phase 2
0.7075	Intermediate Similarity	NPD4629	Approved
0.7075	Intermediate Similarity	NPD5210	Approved
0.7071	Intermediate Similarity	NPD4223	Phase 3
0.7071	Intermediate Similarity	NPD4221	Approved
0.7054	Intermediate Similarity	NPD6614	Approved
0.7034	Intermediate Similarity	NPD6313	Approved
0.7034	Intermediate Similarity	NPD6314	Approved
0.703	Intermediate Similarity	NPD5329	Approved
0.7016	Intermediate Similarity	NPD7319	Approved
0.7009	Intermediate Similarity	NPD6274	Approved
0.7009	Intermediate Similarity	NPD7732	Phase 3
0.6991	Remote Similarity	NPD6686	Approved
0.6989	Remote Similarity	NPD4691	Approved
0.6989	Remote Similarity	NPD4747	Approved
0.6972	Remote Similarity	NPD4700	Approved
0.6961	Remote Similarity	NPD5690	Phase 2
0.6961	Remote Similarity	NPD5279	Phase 3
0.6952	Remote Similarity	NPD8034	Phase 2
0.6952	Remote Similarity	NPD6411	Approved
0.6952	Remote Similarity	NPD8035	Phase 2
0.6949	Remote Similarity	NPD6009	Approved
0.6947	Remote Similarity	NPD4058	Approved
0.6937	Remote Similarity	NPD6052	Approved
0.6931	Remote Similarity	NPD4197	Approved
0.6923	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6917	Remote Similarity	NPD6319	Approved
0.6916	Remote Similarity	NPD5654	Approved
0.6916	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6903	Remote Similarity	NPD6412	Phase 2
0.6887	Remote Similarity	NPD4202	Approved
0.6885	Remote Similarity	NPD7604	Phase 2
0.6882	Remote Similarity	NPD4137	Phase 3
0.6881	Remote Similarity	NPD4225	Approved
0.6875	Remote Similarity	NPD8039	Approved
0.6869	Remote Similarity	NPD4695	Discontinued
0.6863	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.686	Remote Similarity	NPD5983	Phase 2
0.686	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.6847	Remote Similarity	NPD7632	Discontinued
0.6842	Remote Similarity	NPD4729	Approved
0.6842	Remote Similarity	NPD4730	Approved
0.6842	Remote Similarity	NPD5168	Approved
0.6838	Remote Similarity	NPD6858	Approved
0.6838	Remote Similarity	NPD7094	Approved
0.6837	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6829	Remote Similarity	NPD7492	Approved
0.68	Remote Similarity	NPD7736	Approved
0.6796	Remote Similarity	NPD4519	Discontinued
0.6796	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6796	Remote Similarity	NPD4138	Approved
0.6796	Remote Similarity	NPD4689	Approved
0.6796	Remote Similarity	NPD5205	Approved
0.6796	Remote Similarity	NPD4688	Approved
0.6796	Remote Similarity	NPD4690	Approved
0.6796	Remote Similarity	NPD4693	Phase 3
0.6796	Remote Similarity	NPD4623	Approved
0.6792	Remote Similarity	NPD7637	Suspended
0.6789	Remote Similarity	NPD5959	Approved
0.6786	Remote Similarity	NPD4754	Approved
0.6777	Remote Similarity	NPD6054	Approved
0.6774	Remote Similarity	NPD6616	Approved
0.6774	Remote Similarity	NPD6336	Discontinued
0.6772	Remote Similarity	NPD7260	Phase 2
0.6771	Remote Similarity	NPD5733	Approved
0.6771	Remote Similarity	NPD4687	Approved
0.6768	Remote Similarity	NPD4195	Approved
0.6762	Remote Similarity	NPD6101	Approved
0.6762	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6733	Remote Similarity	NPD5209	Approved
0.6729	Remote Similarity	NPD5778	Approved
0.6729	Remote Similarity	NPD5779	Approved
0.6724	Remote Similarity	NPD5249	Phase 3
0.6724	Remote Similarity	NPD5251	Approved
0.6724	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.6724	Remote Similarity	NPD5247	Approved
0.6724	Remote Similarity	NPD5135	Approved
0.6724	Remote Similarity	NPD5250	Approved
0.6724	Remote Similarity	NPD5169	Approved
0.6724	Remote Similarity	NPD5248	Approved
0.6724	Remote Similarity	NPD4634	Approved
0.6721	Remote Similarity	NPD6909	Approved
0.6721	Remote Similarity	NPD6908	Approved
0.6721	Remote Similarity	NPD7503	Approved
0.672	Remote Similarity	NPD7078	Approved
0.6699	Remote Similarity	NPD5363	Approved
0.6697	Remote Similarity	NPD7614	Phase 1
0.6696	Remote Similarity	NPD5128	Approved
0.6667	Remote Similarity	NPD4767	Approved
0.6667	Remote Similarity	NPD3617	Approved
0.6667	Remote Similarity	NPD5215	Approved
0.6667	Remote Similarity	NPD5127	Approved
0.6667	Remote Similarity	NPD5216	Approved
0.6667	Remote Similarity	NPD6404	Discontinued

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