NPASS Compound

Structure

NPC72151 OpenBabel07101719252D 39 41 0 0 1 0 0 0 0 0999 V2000 -3.1653 4.3212 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5909 2.0032 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.1519 6.5651 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.3598 5.5869 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4067 0.9135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5981 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1216 4.7370 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.8126 3.7859 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5254 2.6270 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5472 2.4190 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0997 4.9449 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 0.8660 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9511 -1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8344 3.5780 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2601 1.2601 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2382 1.4680 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5388 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -1.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0000 -1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.5981 -2.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.9511 0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0981 -0.6340 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.4087 5.8959 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 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 2.5981 -1.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 4.3301 -4.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.9074 0.7248 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5388 -0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.0981 -0.6340 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 0.2321 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.7396 6.6391 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 19 1 0 0 0 0 2 20 1 0 0 0 0 3 21 1 0 0 0 0 4 29 1 0 0 0 0 5 29 1 0 0 0 0 9 10 1 0 0 0 0 9 15 2 0 0 0 0 10 19 2 0 0 0 0 11 12 2 0 0 0 0 11 19 1 0 0 0 0 12 22 1 0 0 0 0 13 16 1 0 0 0 0 13 24 1 0 0 0 0 14 17 1 0 0 0 0 14 26 1 0 0 0 0 15 29 1 0 0 0 0 16 31 1 0 0 0 0 17 30 1 0 0 0 0 18 23 1 0 0 0 0 18 25 1 0 0 0 0 20 22 1 0 0 0 0 20 27 2 0 0 0 0 21 33 2 0 0 0 0 21 39 1 0 0 0 0 22 34 2 0 0 0 0 23 27 1 0 0 0 0 23 35 2 0 0 0 0 24 30 1 1 0 0 0 24 32 1 0 0 0 0 25 30 1 6 0 0 0 25 31 1 0 0 0 0 26 32 1 6 0 0 0 26 39 1 0 0 0 0 27 31 1 0 0 0 0 28 32 1 0 0 0 0 28 36 2 0 0 0 0 28 37 1 0 0 0 0 29 38 1 0 0 0 0 30 6 1 1 0 0 0 31 7 1 6 0 0 0 32 8 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	540.31
Volume:	576.799
LogP:	2.773
LogD:	1.906
LogS:	-4.323
# Rotatable Bonds:	9
TPSA:	117.97
# H-Bond Aceptor:	7
# H-Bond Donor:	2
# Rings:	3
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.231
Synthetic Accessibility Score:	5.069
Fsp3:	0.625
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.28
MDCK Permeability:	1.9815441191894934e-05
Pgp-inhibitor:	0.643
Pgp-substrate:	0.032
Human Intestinal Absorption (HIA):	0.005
20% Bioavailability (F20%):	0.002
30% Bioavailability (F30%):	0.013

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.108
Plasma Protein Binding (PPB):	86.35723876953125%
Volume Distribution (VD):	0.494
Pgp-substrate:	9.016358375549316%

ADMET: Metabolism

CYP1A2-inhibitor:	0.015
CYP1A2-substrate:	0.534
CYP2C19-inhibitor:	0.053
CYP2C19-substrate:	0.614
CYP2C9-inhibitor:	0.19
CYP2C9-substrate:	0.948
CYP2D6-inhibitor:	0.094
CYP2D6-substrate:	0.057
CYP3A4-inhibitor:	0.416
CYP3A4-substrate:	0.494

ADMET: Excretion

Clearance (CL):	1.335
Half-life (T1/2):	0.606

ADMET: Toxicity

hERG Blockers:	0.009
Human Hepatotoxicity (H-HT):	0.341
Drug-inuced Liver Injury (DILI):	0.11
AMES Toxicity:	0.06
Rat Oral Acute Toxicity:	0.146
Maximum Recommended Daily Dose:	0.725
Skin Sensitization:	0.413
Carcinogencity:	0.756
Eye Corrosion:	0.004
Eye Irritation:	0.011
Respiratory Toxicity:	0.969

Download Data

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

Natural Product: NPC72151

Natural Product ID:	NPC72151
*Common Name:**	Globostellatic Acids A
IUPAC Name:	(3Z,3aS,5aR,6R,7R,9aR,9bS)-7-acetyloxy-3-[(4E,6E,8E)-10-hydroxy-6,10-dimethyl-3-oxoundeca-4,6,8-trien-2-ylidene]-3a,6,9a-trimethyl-2-oxo-1,4,5,5a,7,8,9,9b-octahydrocyclopenta[a]naphthalene-6-carboxylic acid
Synonyms:
Standard InCHIKey:	FCEBMUDWBVZUAU-JZOYBAOCSA-N
Standard InCHI:	InChI=1S/C32H44O7/c1-19(10-9-15-29(4,5)38)11-12-22(34)20(2)27-23(35)18-25-30(6)17-14-26(39-21(3)33)32(8,28(36)37)24(30)13-16-31(25,27)7/h9-12,15,24-26,38H,13-14,16-18H2,1-8H3,(H,36,37)/b12-11+,15-9+,19-10+,27-20+/t24-,25+,26-,30+,31+,32-/m1/s1
SMILES:	CC(=O)O[C@@H]1CC[C@]2([C@H]([C@@]1(C)C(=O)O)CC[C@]1([C@H]2CC(=O)/C/1=C(C(=O)/C=C/C(=C/C=C/C(O)(C)C)/C)/C)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL524184
PubChem CID:	10530497
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001553] Triterpenoids

*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
NPO28502	Rhabdastrella globostellata	Species	Ancorinidae	Eukaryota	n.a.	n.a.	n.a.	PMID[11858759]
NPO28502	Rhabdastrella globostellata	Species	Ancorinidae	Eukaryota	n.a.	n.a.	n.a.	PMID[16499318]
NPO28502	Rhabdastrella globostellata	Species	Ancorinidae	Eukaryota	n.a.	n.a.	n.a.	PMID[16562838]
NPO28502	Rhabdastrella globostellata	Species	Ancorinidae	Eukaryota	n.a.	n.a.	n.a.	PMID[17524651]
NPO28502	Rhabdastrella globostellata	Species	Ancorinidae	Eukaryota	n.a.	n.a.	n.a.	PMID[20627740]
NPO28502	Rhabdastrella globostellata	Species	Ancorinidae	Eukaryota	n.a.	n.a.	n.a.	PMID[20718449]
NPO28502	Rhabdastrella globostellata	Species	Ancorinidae	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
Others	6

Activity Type	# Activity
Cell Line	6

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1864	Cell Line	L5178Y	Mus musculus	Inhibition	=	100.0	%	PMID[540256]
NPT165	Cell Line	HeLa	Homo sapiens	Inhibition	=	0.0	%	PMID[540256]
NPT681	Cell Line	PC-12	Rattus norvegicus	Inhibition	=	0.0	%	PMID[540256]

☑ 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 NPC72151 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	186
0.1-0.2	921
0.2-0.3	3471
0.3-0.4	7332
0.4-0.5	13808
0.5-0.6	7231
0.6-0.7	6612
0.7-0.8	2890
0.8-0.85	191
0.85-0.9	24
0.9-0.95	24
0.95-1	7

Similarity Score	Similarity Level	Natural Product ID
0.9895	High Similarity	NPC320447
0.9588	High Similarity	NPC329345
0.9588	High Similarity	NPC475526
0.9588	High Similarity	NPC473283
0.9583	High Similarity	NPC282524
0.9495	High Similarity	NPC473284
0.9381	High Similarity	NPC115899
0.9278	High Similarity	NPC35751
0.9278	High Similarity	NPC266955
0.9208	High Similarity	NPC318363
0.9208	High Similarity	NPC475418
0.9208	High Similarity	NPC473482
0.9192	High Similarity	NPC475050
0.9167	High Similarity	NPC301534
0.9167	High Similarity	NPC250757
0.9167	High Similarity	NPC471153
0.9158	High Similarity	NPC473435
0.9158	High Similarity	NPC473431
0.9158	High Similarity	NPC473280
0.9158	High Similarity	NPC471078
0.9118	High Similarity	NPC475065
0.9091	High Similarity	NPC32577
0.9091	High Similarity	NPC114540
0.9091	High Similarity	NPC155332
0.9072	High Similarity	NPC2049
0.9062	High Similarity	NPC88310
0.9062	High Similarity	NPC180950
0.898	High Similarity	NPC108368
0.898	High Similarity	NPC57079
0.8969	High Similarity	NPC122324
0.8969	High Similarity	NPC151725
0.8969	High Similarity	NPC106425
0.8958	High Similarity	NPC299100
0.8947	High Similarity	NPC473986
0.8947	High Similarity	NPC474018
0.8922	High Similarity	NPC329048
0.8922	High Similarity	NPC330011
0.8878	High Similarity	NPC110937
0.8842	High Similarity	NPC474842
0.8842	High Similarity	NPC475965
0.8824	High Similarity	NPC266570
0.8763	High Similarity	NPC474690
0.8762	High Similarity	NPC474315
0.8687	High Similarity	NPC474785
0.8687	High Similarity	NPC474938
0.8679	High Similarity	NPC475970
0.8627	High Similarity	NPC180204
0.8614	High Similarity	NPC118174
0.8614	High Similarity	NPC168319
0.8614	High Similarity	NPC194028
0.86	High Similarity	NPC316598
0.8598	High Similarity	NPC122056
0.8586	High Similarity	NPC242848
0.8519	High Similarity	NPC147912
0.8519	High Similarity	NPC67259
0.8515	High Similarity	NPC477521
0.85	High Similarity	NPC253826
0.8491	Intermediate Similarity	NPC16270
0.8476	Intermediate Similarity	NPC102843
0.8476	Intermediate Similarity	NPC220155
0.8469	Intermediate Similarity	NPC38232
0.8468	Intermediate Similarity	NPC476962
0.8454	Intermediate Similarity	NPC161638
0.8447	Intermediate Similarity	NPC112009
0.8438	Intermediate Similarity	NPC104560
0.8438	Intermediate Similarity	NPC310752
0.8438	Intermediate Similarity	NPC292491
0.8431	Intermediate Similarity	NPC99411
0.8431	Intermediate Similarity	NPC224720
0.8431	Intermediate Similarity	NPC476240
0.8431	Intermediate Similarity	NPC476223
0.84	Intermediate Similarity	NPC327788
0.8396	Intermediate Similarity	NPC475941
0.8396	Intermediate Similarity	NPC474901
0.8367	Intermediate Similarity	NPC252433
0.8367	Intermediate Similarity	NPC470113
0.8364	Intermediate Similarity	NPC167606
0.8364	Intermediate Similarity	NPC470492
0.8364	Intermediate Similarity	NPC286528
0.8364	Intermediate Similarity	NPC20302
0.8364	Intermediate Similarity	NPC140055
0.8351	Intermediate Similarity	NPC118011
0.8351	Intermediate Similarity	NPC36668
0.835	Intermediate Similarity	NPC40918
0.8333	Intermediate Similarity	NPC141292
0.8333	Intermediate Similarity	NPC69291
0.8333	Intermediate Similarity	NPC476274
0.8317	Intermediate Similarity	NPC26413
0.8317	Intermediate Similarity	NPC156546
0.8317	Intermediate Similarity	NPC141401
0.83	Intermediate Similarity	NPC209355
0.83	Intermediate Similarity	NPC84383
0.83	Intermediate Similarity	NPC293052
0.8288	Intermediate Similarity	NPC50774
0.8288	Intermediate Similarity	NPC709
0.8286	Intermediate Similarity	NPC189863
0.8283	Intermediate Similarity	NPC472871
0.8283	Intermediate Similarity	NPC139692
0.8273	Intermediate Similarity	NPC270929
0.8269	Intermediate Similarity	NPC476889
0.8269	Intermediate Similarity	NPC95899
0.8269	Intermediate Similarity	NPC478057
0.8265	Intermediate Similarity	NPC471896
0.8252	Intermediate Similarity	NPC473514
0.8252	Intermediate Similarity	NPC476888
0.8252	Intermediate Similarity	NPC115862
0.8252	Intermediate Similarity	NPC93744
0.8247	Intermediate Similarity	NPC80335
0.8247	Intermediate Similarity	NPC472870
0.8235	Intermediate Similarity	NPC478056
0.8235	Intermediate Similarity	NPC103051
0.8224	Intermediate Similarity	NPC10064
0.8224	Intermediate Similarity	NPC170221
0.8218	Intermediate Similarity	NPC29152
0.8218	Intermediate Similarity	NPC114743
0.8218	Intermediate Similarity	NPC234993
0.8218	Intermediate Similarity	NPC134072
0.8218	Intermediate Similarity	NPC195366
0.8214	Intermediate Similarity	NPC264954
0.8208	Intermediate Similarity	NPC91034
0.8208	Intermediate Similarity	NPC475294
0.8208	Intermediate Similarity	NPC220974
0.82	Intermediate Similarity	NPC469406
0.82	Intermediate Similarity	NPC8993
0.82	Intermediate Similarity	NPC124207
0.8198	Intermediate Similarity	NPC470493
0.8198	Intermediate Similarity	NPC471854
0.8198	Intermediate Similarity	NPC183580
0.8198	Intermediate Similarity	NPC312824
0.8198	Intermediate Similarity	NPC243065
0.819	Intermediate Similarity	NPC472868
0.8182	Intermediate Similarity	NPC177037
0.8182	Intermediate Similarity	NPC475806
0.8182	Intermediate Similarity	NPC472814
0.8182	Intermediate Similarity	NPC204341
0.8173	Intermediate Similarity	NPC22388
0.8173	Intermediate Similarity	NPC473163
0.8173	Intermediate Similarity	NPC476890
0.8173	Intermediate Similarity	NPC136289
0.8165	Intermediate Similarity	NPC264634
0.8165	Intermediate Similarity	NPC147180
0.8163	Intermediate Similarity	NPC262043
0.8163	Intermediate Similarity	NPC66344
0.8163	Intermediate Similarity	NPC474570
0.8155	Intermediate Similarity	NPC474012
0.8155	Intermediate Similarity	NPC476299
0.8155	Intermediate Similarity	NPC201406
0.8155	Intermediate Similarity	NPC117685
0.8155	Intermediate Similarity	NPC471041
0.8155	Intermediate Similarity	NPC471413
0.8155	Intermediate Similarity	NPC470074
0.8148	Intermediate Similarity	NPC179642
0.8148	Intermediate Similarity	NPC6206
0.8144	Intermediate Similarity	NPC128644
0.8142	Intermediate Similarity	NPC474370
0.8137	Intermediate Similarity	NPC53844
0.8137	Intermediate Similarity	NPC108078
0.8137	Intermediate Similarity	NPC99726
0.8131	Intermediate Similarity	NPC472219
0.8131	Intermediate Similarity	NPC472217
0.8131	Intermediate Similarity	NPC472218
0.8125	Intermediate Similarity	NPC329736
0.8119	Intermediate Similarity	NPC476174
0.8119	Intermediate Similarity	NPC171395
0.8119	Intermediate Similarity	NPC139459
0.8119	Intermediate Similarity	NPC279974
0.8113	Intermediate Similarity	NPC34768
0.8113	Intermediate Similarity	NPC472935
0.8108	Intermediate Similarity	NPC64318
0.8108	Intermediate Similarity	NPC476963
0.8105	Intermediate Similarity	NPC279639
0.8105	Intermediate Similarity	NPC3856
0.8105	Intermediate Similarity	NPC476927
0.81	Intermediate Similarity	NPC162615
0.81	Intermediate Similarity	NPC115021
0.81	Intermediate Similarity	NPC214697
0.81	Intermediate Similarity	NPC205034
0.81	Intermediate Similarity	NPC152778
0.8095	Intermediate Similarity	NPC222153
0.8095	Intermediate Similarity	NPC476237
0.8091	Intermediate Similarity	NPC472926
0.8081	Intermediate Similarity	NPC477149
0.8081	Intermediate Similarity	NPC148414
0.8081	Intermediate Similarity	NPC477147
0.8081	Intermediate Similarity	NPC51486
0.8081	Intermediate Similarity	NPC472866
0.8081	Intermediate Similarity	NPC175628
0.8081	Intermediate Similarity	NPC111585
0.8077	Intermediate Similarity	NPC81530
0.8077	Intermediate Similarity	NPC146822
0.8077	Intermediate Similarity	NPC471412
0.8077	Intermediate Similarity	NPC472924
0.807	Intermediate Similarity	NPC67569
0.8061	Intermediate Similarity	NPC117122
0.8061	Intermediate Similarity	NPC48107
0.8061	Intermediate Similarity	NPC72397
0.8058	Intermediate Similarity	NPC235464
0.8058	Intermediate Similarity	NPC166745
0.8058	Intermediate Similarity	NPC98868
0.8058	Intermediate Similarity	NPC119036

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 NPC72151 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	158
0.1-0.2	1114
0.2-0.3	3329
0.3-0.4	2862
0.4-0.5	1071
0.5-0.6	273
0.6-0.7	181
0.7-0.8	148
0.8-0.85	14
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8364	Intermediate Similarity	NPD7115	Discovery
0.8131	Intermediate Similarity	NPD6899	Approved
0.8131	Intermediate Similarity	NPD6881	Approved
0.8073	Intermediate Similarity	NPD8130	Phase 1
0.8037	Intermediate Similarity	NPD5697	Approved
0.802	Intermediate Similarity	NPD7748	Approved
0.8	Intermediate Similarity	NPD8297	Approved
0.7982	Intermediate Similarity	NPD7102	Approved
0.7982	Intermediate Similarity	NPD6883	Approved
0.7982	Intermediate Similarity	NPD7290	Approved
0.7981	Intermediate Similarity	NPD7640	Approved
0.7981	Intermediate Similarity	NPD7639	Approved
0.7944	Intermediate Similarity	NPD6402	Approved
0.7944	Intermediate Similarity	NPD6675	Approved
0.7944	Intermediate Similarity	NPD7128	Approved
0.7944	Intermediate Similarity	NPD5739	Approved
0.7909	Intermediate Similarity	NPD6869	Approved
0.7909	Intermediate Similarity	NPD6649	Approved
0.7909	Intermediate Similarity	NPD6847	Approved
0.7909	Intermediate Similarity	NPD6650	Approved
0.7909	Intermediate Similarity	NPD6617	Approved
0.789	Intermediate Similarity	NPD6013	Approved
0.789	Intermediate Similarity	NPD6012	Approved
0.789	Intermediate Similarity	NPD6014	Approved
0.7885	Intermediate Similarity	NPD4225	Approved
0.7885	Intermediate Similarity	NPD7638	Approved
0.7838	Intermediate Similarity	NPD6882	Approved
0.783	Intermediate Similarity	NPD5211	Phase 2
0.7822	Intermediate Similarity	NPD6079	Approved
0.7822	Intermediate Similarity	NPD7637	Suspended
0.7798	Intermediate Similarity	NPD7320	Approved
0.7798	Intermediate Similarity	NPD6011	Approved
0.7788	Intermediate Similarity	NPD7902	Approved
0.7788	Intermediate Similarity	NPD6084	Phase 2
0.7788	Intermediate Similarity	NPD6083	Phase 2
0.7745	Intermediate Similarity	NPD6399	Phase 3
0.7727	Intermediate Similarity	NPD6373	Approved
0.7727	Intermediate Similarity	NPD6372	Approved
0.7706	Intermediate Similarity	NPD5701	Approved
0.7685	Intermediate Similarity	NPD5141	Approved
0.7677	Intermediate Similarity	NPD7146	Approved
0.7677	Intermediate Similarity	NPD6409	Approved
0.7677	Intermediate Similarity	NPD3618	Phase 1
0.7677	Intermediate Similarity	NPD5330	Approved
0.7677	Intermediate Similarity	NPD7521	Approved
0.7677	Intermediate Similarity	NPD7334	Approved
0.7677	Intermediate Similarity	NPD6684	Approved
0.7677	Intermediate Similarity	NPD3574	Clinical (unspecified phase)
0.7647	Intermediate Similarity	NPD7515	Phase 2
0.7642	Intermediate Similarity	NPD5286	Approved
0.7642	Intermediate Similarity	NPD4696	Approved
0.7642	Intermediate Similarity	NPD5285	Approved
0.7624	Intermediate Similarity	NPD5328	Approved
0.7596	Intermediate Similarity	NPD5695	Phase 3
0.7573	Intermediate Similarity	NPD5779	Approved
0.7573	Intermediate Similarity	NPD5778	Approved
0.7549	Intermediate Similarity	NPD5785	Approved
0.7547	Intermediate Similarity	NPD5696	Approved
0.7525	Intermediate Similarity	NPD6903	Approved
0.7525	Intermediate Similarity	NPD6672	Approved
0.7525	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.7525	Intermediate Similarity	NPD5737	Approved
0.7524	Intermediate Similarity	NPD5221	Approved
0.7524	Intermediate Similarity	NPD5222	Approved
0.7524	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.7521	Intermediate Similarity	NPD6319	Approved
0.75	Intermediate Similarity	NPD5225	Approved
0.75	Intermediate Similarity	NPD4633	Approved
0.75	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD5226	Approved
0.75	Intermediate Similarity	NPD7900	Approved
0.75	Intermediate Similarity	NPD5224	Approved
0.7476	Intermediate Similarity	NPD5281	Approved
0.7476	Intermediate Similarity	NPD5284	Approved
0.7476	Intermediate Similarity	NPD8035	Phase 2
0.7476	Intermediate Similarity	NPD8034	Phase 2
0.7476	Intermediate Similarity	NPD6411	Approved
0.7453	Intermediate Similarity	NPD4755	Approved
0.7453	Intermediate Similarity	NPD5173	Approved
0.7449	Intermediate Similarity	NPD4752	Clinical (unspecified phase)
0.7436	Intermediate Similarity	NPD7100	Approved
0.7436	Intermediate Similarity	NPD7101	Approved
0.7434	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.7431	Intermediate Similarity	NPD5175	Approved
0.7431	Intermediate Similarity	NPD5174	Approved
0.7429	Intermediate Similarity	NPD6356	Clinical (unspecified phase)
0.7426	Intermediate Similarity	NPD3573	Approved
0.7417	Intermediate Similarity	NPD7492	Approved
0.7407	Intermediate Similarity	NPD5223	Approved
0.7404	Intermediate Similarity	NPD4202	Approved
0.74	Intermediate Similarity	NPD5363	Approved
0.74	Intermediate Similarity	NPD1694	Approved
0.7377	Intermediate Similarity	NPD7736	Approved
0.7373	Intermediate Similarity	NPD6054	Approved
0.7355	Intermediate Similarity	NPD6616	Approved
0.735	Intermediate Similarity	NPD6335	Approved
0.7345	Intermediate Similarity	NPD4634	Approved
0.7339	Intermediate Similarity	NPD7632	Discontinued
0.7328	Intermediate Similarity	NPD6274	Approved
0.7328	Intermediate Similarity	NPD6868	Approved
0.7315	Intermediate Similarity	NPD4700	Approved
0.7308	Intermediate Similarity	NPD6050	Approved
0.7308	Intermediate Similarity	NPD5694	Approved
0.7304	Intermediate Similarity	NPD4632	Approved
0.73	Intermediate Similarity	NPD3665	Phase 1
0.73	Intermediate Similarity	NPD3133	Approved
0.73	Intermediate Similarity	NPD3666	Approved
0.73	Intermediate Similarity	NPD4786	Approved
0.7295	Intermediate Similarity	NPD7078	Approved
0.7282	Intermediate Similarity	NPD6904	Approved
0.7282	Intermediate Similarity	NPD5764	Clinical (unspecified phase)
0.7282	Intermediate Similarity	NPD6080	Approved
0.7282	Intermediate Similarity	NPD4753	Phase 2
0.7282	Intermediate Similarity	NPD6673	Approved
0.7282	Intermediate Similarity	NPD6101	Approved
0.7273	Intermediate Similarity	NPD3667	Approved
0.7265	Intermediate Similarity	NPD6317	Approved
0.7264	Intermediate Similarity	NPD5210	Approved
0.7264	Intermediate Similarity	NPD4629	Approved
0.725	Intermediate Similarity	NPD6370	Approved
0.7228	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.7216	Intermediate Similarity	NPD5784	Clinical (unspecified phase)
0.7212	Intermediate Similarity	NPD5207	Approved
0.7212	Intermediate Similarity	NPD5692	Phase 3
0.7203	Intermediate Similarity	NPD6313	Approved
0.7203	Intermediate Similarity	NPD6314	Approved
0.7196	Intermediate Similarity	NPD4697	Phase 3
0.7168	Intermediate Similarity	NPD4729	Approved
0.7168	Intermediate Similarity	NPD4730	Approved
0.7167	Intermediate Similarity	NPD6015	Approved
0.7167	Intermediate Similarity	NPD6016	Approved
0.7157	Intermediate Similarity	NPD4623	Approved
0.7157	Intermediate Similarity	NPD4519	Discontinued
0.7157	Intermediate Similarity	NPD5279	Phase 3
0.7154	Intermediate Similarity	NPD8293	Discontinued
0.7143	Intermediate Similarity	NPD6008	Approved
0.7143	Intermediate Similarity	NPD5693	Phase 1
0.7119	Intermediate Similarity	NPD6009	Approved
0.7107	Intermediate Similarity	NPD5988	Approved
0.71	Intermediate Similarity	NPD4270	Approved
0.71	Intermediate Similarity	NPD4269	Approved
0.71	Intermediate Similarity	NPD4221	Approved
0.71	Intermediate Similarity	NPD4223	Phase 3
0.7083	Intermediate Similarity	NPD6059	Approved
0.7059	Intermediate Similarity	NPD5329	Approved
0.7049	Intermediate Similarity	NPD7604	Phase 2
0.7043	Intermediate Similarity	NPD5247	Approved
0.7043	Intermediate Similarity	NPD5248	Approved
0.7043	Intermediate Similarity	NPD5249	Phase 3
0.7043	Intermediate Similarity	NPD5250	Approved
0.7043	Intermediate Similarity	NPD5251	Approved
0.704	Intermediate Similarity	NPD7319	Approved
0.703	Intermediate Similarity	NPD6695	Phase 3
0.7025	Intermediate Similarity	NPD6909	Approved
0.7025	Intermediate Similarity	NPD6291	Clinical (unspecified phase)
0.7025	Intermediate Similarity	NPD5983	Phase 2
0.7025	Intermediate Similarity	NPD6908	Approved
0.7019	Intermediate Similarity	NPD5208	Approved
0.7018	Intermediate Similarity	NPD6686	Approved
0.7018	Intermediate Similarity	NPD5128	Approved
0.7009	Intermediate Similarity	NPD6001	Approved
0.7	Intermediate Similarity	NPD6404	Discontinued
0.7	Intermediate Similarity	NPD5369	Approved
0.6991	Remote Similarity	NPD4767	Approved
0.6991	Remote Similarity	NPD4768	Approved
0.699	Remote Similarity	NPD5280	Approved
0.699	Remote Similarity	NPD5690	Phase 2
0.699	Remote Similarity	NPD5786	Approved
0.699	Remote Similarity	NPD6098	Approved
0.699	Remote Similarity	NPD4694	Approved
0.6983	Remote Similarity	NPD5217	Approved
0.6983	Remote Similarity	NPD5216	Approved
0.6983	Remote Similarity	NPD5215	Approved
0.6964	Remote Similarity	NPD4754	Approved
0.6961	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6961	Remote Similarity	NPD3668	Phase 3
0.6961	Remote Similarity	NPD4197	Approved
0.6957	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6952	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6944	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6935	Remote Similarity	NPD6336	Discontinued
0.6935	Remote Similarity	NPD7507	Approved
0.6931	Remote Similarity	NPD5209	Approved
0.693	Remote Similarity	NPD6412	Phase 2
0.6923	Remote Similarity	NPD7750	Discontinued
0.69	Remote Similarity	NPD7525	Registered
0.69	Remote Similarity	NPD4252	Approved
0.6897	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6897	Remote Similarity	NPD5169	Approved
0.6897	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.6897	Remote Similarity	NPD5135	Approved
0.6885	Remote Similarity	NPD7503	Approved
0.687	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.687	Remote Similarity	NPD5168	Approved
0.6863	Remote Similarity	NPD7154	Phase 3
0.6863	Remote Similarity	NPD4788	Approved
0.6863	Remote Similarity	NPD5362	Discontinued
0.6847	Remote Similarity	NPD6648	Approved
0.6838	Remote Similarity	NPD5127	Approved
0.6827	Remote Similarity	NPD4690	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