NPASS Compound

Structure

NPC473484 OpenBabel07101719252D 43 47 0 0 1 0 0 0 0 0999 V2000 -0.4896 4.2399 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9375 3.3919 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9583 1.6960 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4687 -1.8271 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8480 2.1855 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3167 1.3376 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4687 4.2399 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5439 6.1022 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6960 5.6126 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3919 5.6126 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.9359 0.2272 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0879 -0.2624 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.9359 1.2064 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2399 0.2272 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6960 4.6335 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3919 4.6335 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0879 2.6751 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2399 3.1647 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8480 3.1647 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6960 2.6751 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3919 1.6960 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9583 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4896 -0.8480 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9583 3.3919 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 1.4688 0.8480 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 5.0879 1.6960 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2399 1.2064 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5439 4.1439 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3919 2.6751 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 2.6751 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9792 1.6960 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.4896 0.8480 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.9792 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4688 -0.8480 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0000 1.6960 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.4688 0.8480 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.0000 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.5439 3.1647 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -0.8480 3.1647 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.4688 -0.8480 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.3167 -1.3376 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.3167 0.3584 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.4896 -0.8480 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 7 1 0 0 0 0 2 24 1 0 0 0 0 7 24 1 0 0 0 0 8 9 2 0 0 0 0 8 10 1 0 0 0 0 9 15 1 0 0 0 0 10 16 2 0 0 0 0 11 12 2 0 0 0 0 11 13 1 0 0 0 0 12 14 1 0 0 0 0 13 26 2 0 0 0 0 14 27 2 0 0 0 0 15 28 2 0 0 0 0 16 28 1 0 0 0 0 17 18 2 0 0 0 0 17 26 1 0 0 0 0 18 29 1 0 0 0 0 19 20 2 0 0 0 0 19 30 1 0 0 0 0 20 38 1 0 0 0 0 21 27 1 0 0 0 0 21 29 2 0 0 0 0 22 25 1 0 0 0 0 22 34 1 0 0 0 0 23 34 1 0 0 0 0 23 37 1 0 0 0 0 24 31 1 0 0 0 0 25 3 1 6 0 0 0 25 32 1 0 0 0 0 26 27 1 0 0 0 0 28 38 1 0 0 0 0 29 38 1 0 0 0 0 30 35 1 0 0 0 0 30 39 2 0 0 0 0 31 35 1 6 0 0 0 31 36 1 0 0 0 0 32 35 1 1 0 0 0 32 37 1 0 0 0 0 33 36 1 0 0 0 0 33 37 1 0 0 0 0 33 40 2 0 0 0 0 34 4 1 6 0 0 0 34 41 1 0 0 0 0 35 5 1 6 0 0 0 36 6 1 6 0 0 0 36 42 1 0 0 0 0 37 43 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	583.33
Volume:	631.672
LogP:	5.496
LogD:	5.031
LogS:	-5.864
# Rotatable Bonds:	7
TPSA:	98.07
# H-Bond Aceptor:	6
# H-Bond Donor:	3
# Rings:	5
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.272
Synthetic Accessibility Score:	5.125
Fsp3:	0.459
Lipinski Rule-of-5:	Rejected
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:	-4.982
MDCK Permeability:	3.50991940649692e-05
Pgp-inhibitor:	0.997
Pgp-substrate:	0.006
Human Intestinal Absorption (HIA):	0.01
20% Bioavailability (F20%):	0.008
30% Bioavailability (F30%):	0.003

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.668
Plasma Protein Binding (PPB):	97.9167251586914%
Volume Distribution (VD):	1.221
Pgp-substrate:	2.1283624172210693%

ADMET: Metabolism

CYP1A2-inhibitor:	0.02
CYP1A2-substrate:	0.821
CYP2C19-inhibitor:	0.871
CYP2C19-substrate:	0.901
CYP2C9-inhibitor:	0.94
CYP2C9-substrate:	0.874
CYP2D6-inhibitor:	0.794
CYP2D6-substrate:	0.08
CYP3A4-inhibitor:	0.974
CYP3A4-substrate:	0.921

ADMET: Excretion

Clearance (CL):	8.783
Half-life (T1/2):	0.332

ADMET: Toxicity

hERG Blockers:	0.268
Human Hepatotoxicity (H-HT):	0.344
Drug-inuced Liver Injury (DILI):	0.977
AMES Toxicity:	0.185
Rat Oral Acute Toxicity:	0.257
Maximum Recommended Daily Dose:	0.311
Skin Sensitization:	0.69
Carcinogencity:	0.078
Eye Corrosion:	0.004
Eye Irritation:	0.083
Respiratory Toxicity:	0.483

Download Data

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

Natural Product: NPC473484

Natural Product ID:	NPC473484
*Common Name:**	10-Hydroxy-18-N-2-Naphthyl-N-Phenylaminobetaenone
IUPAC Name:	(2S,3R,4R,4aR,5R,7R,8aR)-3-butan-2-yl-2,7,8a-trihydroxy-2,4,5,7-tetramethyl-4-[(E)-3-(N-naphthalen-2-ylanilino)prop-2-enoyl]-4a,5,6,8-tetrahydro-3H-naphthalen-1-one
Synonyms:
Standard InCHIKey:	PBODNUVAXAPXJH-YTOGWHTISA-N
Standard InCHI:	InChI=1S/C37H45NO5/c1-7-24(2)31-35(5,32-25(3)22-34(4,41)23-37(32,43)33(40)36(31,6)42)30(39)19-20-38(28-15-9-8-10-16-28)29-18-17-26-13-11-12-14-27(26)21-29/h8-21,24-25,31-32,41-43H,7,22-23H2,1-6H3/b20-19+/t24?,25-,31-,32-,34-,35-,36+,37-/m1/s1
SMILES:	CCC(C)C1C(C2C(CC(CC2(C(=O)C1(C)O)O)(C)O)C)(C)C(=O)C=CN(C3=CC=CC=C3)C4=CC5=CC=CC=C5C=C4
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL443169
PubChem CID:	10674806
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0000023] Naphthalenes

*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
NPO33476	microsphaeropsis sp.	Species	n.a.	Eukaryota	n.a.	n.a.	n.a.	PMID[10869191]
NPO33476	microsphaeropsis sp.	Species	n.a.	Eukaryota	n.a.	n.a.	n.a.	PMID[12027766]
NPO33476	microsphaeropsis sp.	Species	n.a.	Eukaryota	n.a.	n.a.	n.a.	PMID[32243151]
NPO33476	microsphaeropsis sp.	Species	n.a.	Eukaryota	n.a.	n.a.	n.a.	PMID[9917295]

☑ 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
Individual Protein	2
Protein Complex	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT6611	Individual Protein	Protein kinase C epsilon	Mus musculus	IC50	>	100000.0	nM	PMID[486003]
NPT285	Individual Protein	Epidermal growth factor receptor erbB1	Homo sapiens	IC50	>	100000.0	nM	PMID[486003]
NPT1560	Protein Complex	Cyclin-dependent kinase 4/cyclin D1	Homo sapiens	IC50	>	100000.0	nM	PMID[486003]

☑ 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 NPC473484 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	282
0.1-0.2	1344
0.2-0.3	3914
0.3-0.4	11541
0.4-0.5	20668
0.5-0.6	4577
0.6-0.7	369
0.7-0.8	1
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.7095	Intermediate Similarity	NPC126676
0.7095	Intermediate Similarity	NPC469671
0.6941	Remote Similarity	NPC470579
0.6893	Remote Similarity	NPC315368
0.6842	Remote Similarity	NPC313293
0.6802	Remote Similarity	NPC212799
0.6686	Remote Similarity	NPC315051
0.6615	Remote Similarity	NPC181502
0.6615	Remote Similarity	NPC85066
0.6614	Remote Similarity	NPC470317
0.6613	Remote Similarity	NPC475427
0.6595	Remote Similarity	NPC307640
0.6588	Remote Similarity	NPC472243
0.6545	Remote Similarity	NPC314431
0.6545	Remote Similarity	NPC52262
0.6541	Remote Similarity	NPC226143
0.6532	Remote Similarity	NPC311330
0.6531	Remote Similarity	NPC198205
0.6531	Remote Similarity	NPC221687
0.6531	Remote Similarity	NPC21483
0.6519	Remote Similarity	NPC225319
0.65	Remote Similarity	NPC104345
0.65	Remote Similarity	NPC471512
0.6497	Remote Similarity	NPC473375
0.6497	Remote Similarity	NPC97100
0.6486	Remote Similarity	NPC469915
0.6485	Remote Similarity	NPC133156
0.648	Remote Similarity	NPC114808
0.6468	Remote Similarity	NPC475223
0.6465	Remote Similarity	NPC198390
0.6463	Remote Similarity	NPC119326
0.6436	Remote Similarity	NPC246983
0.6436	Remote Similarity	NPC475448
0.6436	Remote Similarity	NPC471743
0.6432	Remote Similarity	NPC63047
0.6432	Remote Similarity	NPC112752
0.6432	Remote Similarity	NPC311054
0.6432	Remote Similarity	NPC475248
0.6429	Remote Similarity	NPC73644
0.6429	Remote Similarity	NPC201424
0.6416	Remote Similarity	NPC472241
0.6402	Remote Similarity	NPC472244
0.6402	Remote Similarity	NPC470343
0.64	Remote Similarity	NPC472242
0.64	Remote Similarity	NPC107828
0.64	Remote Similarity	NPC90358
0.6398	Remote Similarity	NPC472680
0.6398	Remote Similarity	NPC472679
0.6393	Remote Similarity	NPC282339
0.6393	Remote Similarity	NPC99632
0.6393	Remote Similarity	NPC469741
0.6383	Remote Similarity	NPC475097
0.6364	Remote Similarity	NPC478039
0.6358	Remote Similarity	NPC257490
0.6354	Remote Similarity	NPC477157
0.6354	Remote Similarity	NPC477156
0.6341	Remote Similarity	NPC472681
0.6337	Remote Similarity	NPC136573
0.6337	Remote Similarity	NPC471489
0.6337	Remote Similarity	NPC176371
0.6335	Remote Similarity	NPC471997
0.6335	Remote Similarity	NPC286994
0.633	Remote Similarity	NPC477976
0.6328	Remote Similarity	NPC94602
0.6327	Remote Similarity	NPC22689
0.6327	Remote Similarity	NPC105055
0.6318	Remote Similarity	NPC475406
0.6308	Remote Similarity	NPC127026
0.6308	Remote Similarity	NPC127720
0.6307	Remote Similarity	NPC260194
0.6304	Remote Similarity	NPC472117
0.6304	Remote Similarity	NPC199737
0.6296	Remote Similarity	NPC112373
0.6296	Remote Similarity	NPC161956
0.6296	Remote Similarity	NPC267926
0.6296	Remote Similarity	NPC258531
0.6291	Remote Similarity	NPC61813
0.629	Remote Similarity	NPC327904
0.629	Remote Similarity	NPC38959
0.6289	Remote Similarity	NPC49184
0.6287	Remote Similarity	NPC150863
0.6284	Remote Similarity	NPC36495
0.6283	Remote Similarity	NPC474815
0.628	Remote Similarity	NPC284102
0.6279	Remote Similarity	NPC471980
0.6277	Remote Similarity	NPC474814
0.6277	Remote Similarity	NPC112336
0.6277	Remote Similarity	NPC318183
0.6276	Remote Similarity	NPC477998
0.6272	Remote Similarity	NPC53044
0.6271	Remote Similarity	NPC473541
0.6267	Remote Similarity	NPC475648
0.6256	Remote Similarity	NPC475596
0.6256	Remote Similarity	NPC475303
0.6256	Remote Similarity	NPC473781
0.6256	Remote Similarity	NPC99428
0.6256	Remote Similarity	NPC35390
0.6256	Remote Similarity	NPC470631
0.6256	Remote Similarity	NPC316841
0.625	Remote Similarity	NPC245756
0.625	Remote Similarity	NPC472245
0.625	Remote Similarity	NPC280807
0.625	Remote Similarity	NPC11149
0.6244	Remote Similarity	NPC223590
0.6242	Remote Similarity	NPC192533
0.6238	Remote Similarity	NPC317727
0.6237	Remote Similarity	NPC472106
0.6236	Remote Similarity	NPC2672
0.6235	Remote Similarity	NPC177684
0.6235	Remote Similarity	NPC291962
0.6233	Remote Similarity	NPC106593
0.6229	Remote Similarity	NPC475128
0.6227	Remote Similarity	NPC30456
0.6227	Remote Similarity	NPC475316
0.6227	Remote Similarity	NPC473486
0.6226	Remote Similarity	NPC96131
0.6226	Remote Similarity	NPC473837
0.6223	Remote Similarity	NPC30171
0.6219	Remote Similarity	NPC36607
0.6219	Remote Similarity	NPC90967
0.6216	Remote Similarity	NPC253667
0.6216	Remote Similarity	NPC35510
0.6216	Remote Similarity	NPC472101
0.6216	Remote Similarity	NPC472120
0.6215	Remote Similarity	NPC140311
0.6205	Remote Similarity	NPC79698
0.6204	Remote Similarity	NPC266192
0.6197	Remote Similarity	NPC212768
0.6197	Remote Similarity	NPC473115
0.6197	Remote Similarity	NPC75600
0.6197	Remote Similarity	NPC158020
0.6197	Remote Similarity	NPC473089
0.6197	Remote Similarity	NPC6576
0.6193	Remote Similarity	NPC320088
0.6188	Remote Similarity	NPC17677
0.6186	Remote Similarity	NPC477912
0.6182	Remote Similarity	NPC96801
0.6182	Remote Similarity	NPC150698
0.6182	Remote Similarity	NPC473689
0.6182	Remote Similarity	NPC292416
0.6181	Remote Similarity	NPC47190
0.618	Remote Similarity	NPC264589
0.6179	Remote Similarity	NPC477907
0.6179	Remote Similarity	NPC42678
0.6179	Remote Similarity	NPC477909
0.6179	Remote Similarity	NPC203614
0.6175	Remote Similarity	NPC141428
0.6175	Remote Similarity	NPC328154
0.6172	Remote Similarity	NPC124086
0.617	Remote Similarity	NPC224970
0.617	Remote Similarity	NPC167724
0.617	Remote Similarity	NPC223595
0.6168	Remote Similarity	NPC301368
0.6168	Remote Similarity	NPC84815
0.6167	Remote Similarity	NPC144691
0.6165	Remote Similarity	NPC329833
0.6162	Remote Similarity	NPC472102
0.6162	Remote Similarity	NPC309531
0.6158	Remote Similarity	NPC473880
0.6158	Remote Similarity	NPC473743
0.6154	Remote Similarity	NPC200743
0.6154	Remote Similarity	NPC97584
0.6154	Remote Similarity	NPC244839
0.6154	Remote Similarity	NPC320324
0.6154	Remote Similarity	NPC319880
0.6149	Remote Similarity	NPC153007
0.6143	Remote Similarity	NPC204303
0.614	Remote Similarity	NPC313663
0.6135	Remote Similarity	NPC18661
0.6134	Remote Similarity	NPC190461
0.6133	Remote Similarity	NPC66936
0.6133	Remote Similarity	NPC471782
0.6133	Remote Similarity	NPC471583
0.6133	Remote Similarity	NPC253482
0.6132	Remote Similarity	NPC471284
0.6129	Remote Similarity	NPC473667
0.6129	Remote Similarity	NPC476231
0.6127	Remote Similarity	NPC475489
0.6126	Remote Similarity	NPC237702
0.6124	Remote Similarity	NPC116519
0.6121	Remote Similarity	NPC39818
0.6121	Remote Similarity	NPC62367
0.612	Remote Similarity	NPC473297
0.6119	Remote Similarity	NPC475631
0.6119	Remote Similarity	NPC57690
0.6119	Remote Similarity	NPC228377
0.6119	Remote Similarity	NPC211920
0.6119	Remote Similarity	NPC475600
0.6119	Remote Similarity	NPC476110
0.6119	Remote Similarity	NPC87152
0.6119	Remote Similarity	NPC328186
0.6119	Remote Similarity	NPC477787
0.6119	Remote Similarity	NPC122968
0.6118	Remote Similarity	NPC316746
0.6118	Remote Similarity	NPC183722
0.6114	Remote Similarity	NPC235900
0.6114	Remote Similarity	NPC99043
0.6114	Remote Similarity	NPC218594
0.6111	Remote Similarity	NPC242000
0.6111	Remote Similarity	NPC477903

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 NPC473484 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	180
0.1-0.2	615
0.2-0.3	816
0.3-0.4	1512
0.4-0.5	4030
0.5-0.6	1863
0.6-0.7	126
0.7-0.8	8
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.7702	Intermediate Similarity	NPD7082	Approved
0.7542	Intermediate Similarity	NPD8658	Clinical (unspecified phase)
0.7444	Intermediate Similarity	NPD7962	Phase 2
0.7439	Intermediate Similarity	NPD7259	Approved
0.7394	Intermediate Similarity	NPD7295	Approved
0.7305	Intermediate Similarity	NPD7478	Approved
0.7278	Intermediate Similarity	NPD7606	Phase 3
0.7202	Intermediate Similarity	NPD7794	Clinical (unspecified phase)
0.7126	Intermediate Similarity	NPD7487	Discontinued
0.6944	Remote Similarity	NPD7795	Phase 2
0.6911	Remote Similarity	NPD5610	Approved
0.6897	Remote Similarity	NPD5086	Approved
0.6864	Remote Similarity	NPD2820	Phase 3
0.6805	Remote Similarity	NPD2365	Approved
0.67	Remote Similarity	NPD7927	Clinical (unspecified phase)
0.6595	Remote Similarity	NPD7854	Phase 2
0.6588	Remote Similarity	NPD6522	Clinical (unspecified phase)
0.6571	Remote Similarity	NPD4888	Discontinued
0.6559	Remote Similarity	NPD5466	Approved
0.6526	Remote Similarity	NPD8281	Discontinued
0.6505	Remote Similarity	NPD7301	Phase 3
0.6503	Remote Similarity	NPD6320	Approved
0.6481	Remote Similarity	NPD1360	Approved
0.6471	Remote Similarity	NPD5919	Clinical (unspecified phase)
0.6468	Remote Similarity	NPD7187	Phase 2
0.6467	Remote Similarity	NPD8003	Clinical (unspecified phase)
0.6467	Remote Similarity	NPD8002	Clinical (unspecified phase)
0.6453	Remote Similarity	NPD2010	Phase 3
0.6448	Remote Similarity	NPD8007	Approved
0.6448	Remote Similarity	NPD8008	Approved
0.6429	Remote Similarity	NPD7293	Approved
0.6429	Remote Similarity	NPD8146	Phase 2
0.6402	Remote Similarity	NPD8006	Clinical (unspecified phase)
0.64	Remote Similarity	NPD6622	Phase 1
0.6382	Remote Similarity	NPD7238	Clinical (unspecified phase)
0.6379	Remote Similarity	NPD4430	Phase 2
0.6374	Remote Similarity	NPD6342	Discontinued
0.6368	Remote Similarity	NPD7881	Approved
0.6335	Remote Similarity	NPD6293	Clinical (unspecified phase)
0.6335	Remote Similarity	NPD6496	Clinical (unspecified phase)
0.6333	Remote Similarity	NPD2790	Discontinued
0.6331	Remote Similarity	NPD6740	Clinical (unspecified phase)
0.6331	Remote Similarity	NPD1527	Phase 2
0.6327	Remote Similarity	NPD5928	Phase 1
0.6322	Remote Similarity	NPD6768	Approved
0.6296	Remote Similarity	NPD7449	Clinical (unspecified phase)
0.6294	Remote Similarity	NPD5182	Approved
0.6294	Remote Similarity	NPD5185	Approved
0.6294	Remote Similarity	NPD5184	Approved
0.6294	Remote Similarity	NPD5504	Discontinued
0.6294	Remote Similarity	NPD6630	Clinical (unspecified phase)
0.6286	Remote Similarity	NPD1625	Approved
0.6284	Remote Similarity	NPD7599	Phase 2
0.6277	Remote Similarity	NPD7663	Clinical (unspecified phase)
0.6276	Remote Similarity	NPD7233	Approved
0.6276	Remote Similarity	NPD7234	Approved
0.6273	Remote Similarity	NPD1668	Clinical (unspecified phase)
0.6271	Remote Similarity	NPD1956	Clinical (unspecified phase)
0.6257	Remote Similarity	NPD2331	Discontinued
0.6257	Remote Similarity	NPD2470	Clinical (unspecified phase)
0.625	Remote Similarity	NPD5992	Approved
0.625	Remote Similarity	NPD7600	Phase 2
0.625	Remote Similarity	NPD6833	Clinical (unspecified phase)
0.6244	Remote Similarity	NPD6987	Phase 1
0.6243	Remote Similarity	NPD5997	Discontinued
0.6238	Remote Similarity	NPD5609	Approved
0.6238	Remote Similarity	NPD5608	Approved
0.6237	Remote Similarity	NPD5430	Discontinued
0.6236	Remote Similarity	NPD8165	Discontinued
0.6235	Remote Similarity	NPD1874	Clinical (unspecified phase)
0.6232	Remote Similarity	NPD7302	Phase 3
0.6232	Remote Similarity	NPD7191	Phase 2
0.6232	Remote Similarity	NPD7300	Phase 3
0.623	Remote Similarity	NPD5715	Clinical (unspecified phase)
0.623	Remote Similarity	NPD8060	Phase 1
0.6215	Remote Similarity	NPD5931	Phase 3
0.6215	Remote Similarity	NPD8239	Clinical (unspecified phase)
0.6215	Remote Similarity	NPD5933	Phase 3
0.6215	Remote Similarity	NPD5932	Phase 3
0.6211	Remote Similarity	NPD5033	Approved
0.6211	Remote Similarity	NPD7662	Clinical (unspecified phase)
0.6211	Remote Similarity	NPD7940	Phase 3
0.6207	Remote Similarity	NPD6606	Clinical (unspecified phase)
0.6198	Remote Similarity	NPD4956	Approved
0.6167	Remote Similarity	NPD5748	Phase 2
0.6163	Remote Similarity	NPD1410	Phase 1
0.6162	Remote Similarity	NPD7244	Discontinued
0.6158	Remote Similarity	NPD5918	Discontinued
0.6154	Remote Similarity	NPD2919	Clinical (unspecified phase)
0.6154	Remote Similarity	NPD2918	Clinical (unspecified phase)
0.6154	Remote Similarity	NPD8354	Approved
0.6149	Remote Similarity	NPD1626	Approved
0.6149	Remote Similarity	NPD7254	Discontinued
0.6146	Remote Similarity	NPD5498	Phase 2
0.6145	Remote Similarity	NPD7088	Discontinued
0.6141	Remote Similarity	NPD8630	Approved
0.614	Remote Similarity	NPD7858	Clinical (unspecified phase)
0.614	Remote Similarity	NPD7714	Approved
0.614	Remote Similarity	NPD7715	Approved
0.6136	Remote Similarity	NPD6513	Approved
0.6136	Remote Similarity	NPD6566	Discontinued
0.6136	Remote Similarity	NPD6512	Approved
0.6134	Remote Similarity	NPD5039	Approved
0.6133	Remote Similarity	NPD8353	Approved
0.6133	Remote Similarity	NPD8355	Approved
0.6132	Remote Similarity	NPD7707	Approved
0.6127	Remote Similarity	NPD8248	Clinical (unspecified phase)
0.6124	Remote Similarity	NPD7785	Clinical (unspecified phase)
0.6122	Remote Similarity	NPD8167	Discontinued
0.6118	Remote Similarity	NPD1069	Approved
0.6118	Remote Similarity	NPD1070	Approved
0.6115	Remote Similarity	NPD7633	Discontinued
0.6114	Remote Similarity	NPD7775	Approved
0.6114	Remote Similarity	NPD989	Approved
0.6108	Remote Similarity	NPD4335	Clinical (unspecified phase)
0.6105	Remote Similarity	NPD8051	Clinical (unspecified phase)
0.6103	Remote Similarity	NPD5522	Clinical (unspecified phase)
0.6102	Remote Similarity	NPD5024	Approved
0.61	Remote Similarity	NPD5937	Approved
0.6095	Remote Similarity	NPD6204	Clinical (unspecified phase)
0.6094	Remote Similarity	NPD6375	Clinical (unspecified phase)
0.6091	Remote Similarity	NPD7654	Discontinued
0.6089	Remote Similarity	NPD6416	Phase 2
0.6089	Remote Similarity	NPD3141	Discontinued
0.6087	Remote Similarity	NPD7091	Discontinued
0.6087	Remote Similarity	NPD6571	Approved
0.6087	Remote Similarity	NPD6570	Approved
0.6085	Remote Similarity	NPD7581	Clinical (unspecified phase)
0.6085	Remote Similarity	NPD7580	Phase 3
0.6082	Remote Similarity	NPD4330	Approved
0.6082	Remote Similarity	NPD4329	Approved
0.608	Remote Similarity	NPD3625	Discontinued
0.6078	Remote Similarity	NPD4734	Approved
0.6078	Remote Similarity	NPD4735	Approved
0.6073	Remote Similarity	NPD3377	Discontinued
0.6067	Remote Similarity	NPD6506	Clinical (unspecified phase)
0.6064	Remote Similarity	NPD7035	Approved
0.6064	Remote Similarity	NPD7591	Clinical (unspecified phase)
0.6064	Remote Similarity	NPD7036	Phase 3
0.6062	Remote Similarity	NPD3792	Approved
0.6061	Remote Similarity	NPD6483	Approved
0.6061	Remote Similarity	NPD6484	Approved
0.6059	Remote Similarity	NPD8485	Approved
0.6057	Remote Similarity	NPD6655	Clinical (unspecified phase)
0.6056	Remote Similarity	NPD7441	Clinical (unspecified phase)
0.6053	Remote Similarity	NPD2369	Discontinued
0.6051	Remote Similarity	NPD3470	Approved
0.6051	Remote Similarity	NPD3471	Approved
0.6045	Remote Similarity	NPD3482	Approved
0.6042	Remote Similarity	NPD7324	Discontinued
0.6041	Remote Similarity	NPD6163	Clinical (unspecified phase)
0.6034	Remote Similarity	NPD7602	Clinical (unspecified phase)
0.6034	Remote Similarity	NPD6017	Discontinued
0.6031	Remote Similarity	NPD7771	Discontinued
0.6031	Remote Similarity	NPD3782	Discontinued
0.6031	Remote Similarity	NPD7479	Phase 2
0.603	Remote Similarity	NPD6835	Approved
0.6029	Remote Similarity	NPD5194	Approved
0.6029	Remote Similarity	NPD7778	Approved
0.6029	Remote Similarity	NPD5197	Approved
0.6029	Remote Similarity	NPD5196	Approved
0.6029	Remote Similarity	NPD7777	Approved
0.6029	Remote Similarity	NPD53	Approved
0.6024	Remote Similarity	NPD4775	Clinical (unspecified phase)
0.6022	Remote Similarity	NPD33	Approved
0.6022	Remote Similarity	NPD4393	Approved
0.6021	Remote Similarity	NPD3776	Discontinued
0.6013	Remote Similarity	NPD4116	Approved
0.6012	Remote Similarity	NPD5578	Approved
0.6012	Remote Similarity	NPD5577	Clinical (unspecified phase)
0.6012	Remote Similarity	NPD1036	Approved
0.6011	Remote Similarity	NPD6707	Clinical (unspecified phase)
0.6	Remote Similarity	NPD6855	Clinical (unspecified phase)
0.6	Remote Similarity	NPD5896	Clinical (unspecified phase)
0.6	Remote Similarity	NPD8360	Approved
0.6	Remote Similarity	NPD5921	Clinical (unspecified phase)
0.6	Remote Similarity	NPD8361	Approved
0.6	Remote Similarity	NPD6661	Clinical (unspecified phase)
0.6	Remote Similarity	NPD8435	Approved
0.6	Remote Similarity	NPD6211	Clinical (unspecified phase)
0.599	Remote Similarity	NPD5721	Clinical (unspecified phase)
0.599	Remote Similarity	NPD4412	Phase 2
0.5989	Remote Similarity	NPD2506	Approved
0.5989	Remote Similarity	NPD6789	Approved
0.5989	Remote Similarity	NPD7720	Phase 2
0.5989	Remote Similarity	NPD2737	Clinical (unspecified phase)
0.5989	Remote Similarity	NPD3434	Clinical (unspecified phase)
0.5989	Remote Similarity	NPD4461	Discontinued
0.5988	Remote Similarity	NPD2846	Clinical (unspecified phase)
0.5981	Remote Similarity	NPD7957	Phase 1
0.5981	Remote Similarity	NPD7958	Clinical (unspecified phase)
0.598	Remote Similarity	NPD8424	Clinical (unspecified phase)
0.598	Remote Similarity	NPD6161	Approved
0.598	Remote Similarity	NPD6162	Approved
0.5978	Remote Similarity	NPD3481	Approved
0.5978	Remote Similarity	NPD7774	Clinical (unspecified phase)
0.5978	Remote Similarity	NPD7612	Clinical (unspecified phase)
0.5978	Remote Similarity	NPD4046	Approved
0.5978	Remote Similarity	NPD4043	Approved
0.5977	Remote Similarity	NPD2791	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