NPASS Compound

Structure

NPC33742 OpenBabel07101718192D 31 32 0 0 1 0 0 0 0 0999 V2000 6.0622 -10.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9282 -10.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9282 -9.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 -8.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 -7.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 -7.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 -6.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -5.5000 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 3.4641 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -4.5000 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 2.5981 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.5981 -2.5000 0.0000 C 0 0 1 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 0.0000 -1.0000 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 -0.0000 -0.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -2.5000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -3.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -4.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -4.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 3 2 0 0 0 0 2 28 1 0 0 0 0 3 4 1 0 0 0 0 4 5 1 0 0 0 0 5 6 1 0 0 0 0 6 7 1 0 0 0 0 7 8 1 0 0 0 0 8 12 1 0 0 0 0 9 10 2 0 0 0 0 9 11 1 0 0 0 0 10 14 1 0 0 0 0 11 15 2 0 0 0 0 12 17 1 0 0 0 0 13 16 1 0 0 0 0 13 18 1 0 0 0 0 14 20 2 0 0 0 0 15 20 1 0 0 0 0 16 21 1 0 0 0 0 17 23 1 0 0 0 0 18 26 1 0 0 0 0 19 20 1 0 0 0 0 21 24 1 0 0 0 0 21 27 1 6 0 0 0 22 19 1 6 0 0 0 22 25 1 0 0 0 0 22 28 1 0 0 0 0 23 28 1 0 0 0 0 23 29 2 0 0 0 0 24 26 2 0 0 0 0 24 30 1 0 0 0 0 25 27 2 3 0 0 0 25 31 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	427.28
Volume:	464.749
LogP:	3.73
LogD:	3.701
LogS:	-3.548
# Rotatable Bonds:	15
TPSA:	78.51
# H-Bond Aceptor:	6
# H-Bond Donor:	2
# Rings:	2
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.374
Synthetic Accessibility Score:	3.221
Fsp3:	0.56
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.677
MDCK Permeability:	3.518921585055068e-05
Pgp-inhibitor:	0.231
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.171
20% Bioavailability (F20%):	0.411
30% Bioavailability (F30%):	0.844

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.672
Plasma Protein Binding (PPB):	86.13436126708984%
Volume Distribution (VD):	0.608
Pgp-substrate:	9.49817943572998%

ADMET: Metabolism

CYP1A2-inhibitor:	0.028
CYP1A2-substrate:	0.186
CYP2C19-inhibitor:	0.545
CYP2C19-substrate:	0.475
CYP2C9-inhibitor:	0.578
CYP2C9-substrate:	0.469
CYP2D6-inhibitor:	0.133
CYP2D6-substrate:	0.346
CYP3A4-inhibitor:	0.947
CYP3A4-substrate:	0.265

ADMET: Excretion

Clearance (CL):	4.697
Half-life (T1/2):	0.624

ADMET: Toxicity

hERG Blockers:	0.023
Human Hepatotoxicity (H-HT):	0.121
Drug-inuced Liver Injury (DILI):	0.04
AMES Toxicity:	0.016
Rat Oral Acute Toxicity:	0.838
Maximum Recommended Daily Dose:	0.139
Skin Sensitization:	0.576
Carcinogencity:	0.056
Eye Corrosion:	0.003
Eye Irritation:	0.009
Respiratory Toxicity:	0.044

Download Data

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

Natural Product: NPC33742

Natural Product ID:	NPC33742
*Common Name:**	Ciliatamides C
IUPAC Name:	N-methyl-N-[(2S)-1-oxo-1-[[(3S)-2-oxopiperidin-3-yl]amino]-3-phenylpropan-2-yl]dec-9-enamide
Synonyms:	Ciliatamides C
Standard InCHIKey:	KBRMYAFKZQPUNJ-VXKWHMMOSA-N
Standard InCHI:	InChI=1S/C25H37N3O3/c1-3-4-5-6-7-8-12-17-23(29)28(2)22(19-20-14-10-9-11-15-20)25(31)27-21-16-13-18-26-24(21)30/h3,9-11,14-15,21-22H,1,4-8,12-13,16-19H2,2H3,(H,26,30)(H,27,31)/t21-,22-/m0/s1
SMILES:	C=CCCCCCCCC(=O)N(C)[C@@H](Cc1ccccc1)C(=N[C@H]1CCCN=C1O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL403314
PubChem CID:	24854118
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000264] Organic acids and derivatives [CHEMONTID:0000265] Carboxylic acids and derivatives [CHEMONTID:0000013] Amino acids, peptides, and analogues [CHEMONTID:0000348] Peptides [CHEMONTID:0004830] Dipeptides

*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
NPO8025	Aaptos ciliata	Species	Suberitidae	Eukaryota	n.a.	n.a.	n.a.	PMID[18257536]
NPO8025	Aaptos ciliata	Species	Suberitidae	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

Activity Type	# Activity
Cell Line	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT165	Cell Line	HeLa	Homo sapiens	IC50	=	50.0	ug.mL-1	PMID[509492]

☑ 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 NPC33742 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	114
0.1-0.2	1066
0.2-0.3	6459
0.3-0.4	18497
0.4-0.5	13093
0.5-0.6	2562
0.6-0.7	607
0.7-0.8	264
0.8-0.85	26
0.85-0.9	6
0.9-0.95	2
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9358	High Similarity	NPC35850
0.9358	High Similarity	NPC276949
0.8938	High Similarity	NPC285926
0.8938	High Similarity	NPC315276
0.8938	High Similarity	NPC14672
0.886	High Similarity	NPC470545
0.8783	High Similarity	NPC470546
0.8772	High Similarity	NPC470544
0.8632	High Similarity	NPC200964
0.8559	High Similarity	NPC71684
0.8525	High Similarity	NPC111428
0.843	Intermediate Similarity	NPC101719
0.8417	Intermediate Similarity	NPC6975
0.8417	Intermediate Similarity	NPC474082
0.8417	Intermediate Similarity	NPC175726
0.8387	Intermediate Similarity	NPC255447
0.8374	Intermediate Similarity	NPC473322
0.8347	Intermediate Similarity	NPC222466
0.825	Intermediate Similarity	NPC202521
0.8167	Intermediate Similarity	NPC476990
0.816	Intermediate Similarity	NPC200589
0.8151	Intermediate Similarity	NPC220698
0.8136	Intermediate Similarity	NPC239357
0.8131	Intermediate Similarity	NPC303045
0.8131	Intermediate Similarity	NPC161972
0.8053	Intermediate Similarity	NPC45033
0.8047	Intermediate Similarity	NPC248283
0.8033	Intermediate Similarity	NPC252878
0.8019	Intermediate Similarity	NPC226438
0.8	Intermediate Similarity	NPC12730
0.7982	Intermediate Similarity	NPC311242
0.7967	Intermediate Similarity	NPC46427
0.7953	Intermediate Similarity	NPC130309
0.7949	Intermediate Similarity	NPC474584
0.7946	Intermediate Similarity	NPC471317
0.7931	Intermediate Similarity	NPC319579
0.7903	Intermediate Similarity	NPC22746
0.789	Intermediate Similarity	NPC25565
0.7874	Intermediate Similarity	NPC300315
0.7863	Intermediate Similarity	NPC242159
0.7863	Intermediate Similarity	NPC313694
0.7863	Intermediate Similarity	NPC132636
0.7857	Intermediate Similarity	NPC319766
0.7818	Intermediate Similarity	NPC475439
0.7818	Intermediate Similarity	NPC473501
0.7788	Intermediate Similarity	NPC164859
0.7752	Intermediate Similarity	NPC325479
0.7748	Intermediate Similarity	NPC322598
0.7739	Intermediate Similarity	NPC327481
0.7704	Intermediate Similarity	NPC471680
0.7704	Intermediate Similarity	NPC209509
0.7692	Intermediate Similarity	NPC287401
0.7687	Intermediate Similarity	NPC161069
0.7669	Intermediate Similarity	NPC163392
0.7669	Intermediate Similarity	NPC239762
0.7656	Intermediate Similarity	NPC469666
0.7652	Intermediate Similarity	NPC471264
0.7652	Intermediate Similarity	NPC471265
0.7652	Intermediate Similarity	NPC473418
0.7638	Intermediate Similarity	NPC477937
0.763	Intermediate Similarity	NPC476978
0.7623	Intermediate Similarity	NPC169328
0.7612	Intermediate Similarity	NPC263493
0.7612	Intermediate Similarity	NPC269398
0.7594	Intermediate Similarity	NPC98424
0.7594	Intermediate Similarity	NPC470884
0.7594	Intermediate Similarity	NPC92784
0.7594	Intermediate Similarity	NPC178662
0.7594	Intermediate Similarity	NPC476133
0.7591	Intermediate Similarity	NPC16188
0.7586	Intermediate Similarity	NPC473498
0.7574	Intermediate Similarity	NPC5620
0.7563	Intermediate Similarity	NPC329011
0.7561	Intermediate Similarity	NPC310467
0.7556	Intermediate Similarity	NPC139326
0.7519	Intermediate Similarity	NPC127741
0.7519	Intermediate Similarity	NPC68865
0.75	Intermediate Similarity	NPC67043
0.7478	Intermediate Similarity	NPC202613
0.7477	Intermediate Similarity	NPC256452
0.7464	Intermediate Similarity	NPC138775
0.7459	Intermediate Similarity	NPC197470
0.744	Intermediate Similarity	NPC478015
0.744	Intermediate Similarity	NPC27833
0.744	Intermediate Similarity	NPC478016
0.744	Intermediate Similarity	NPC478014
0.7431	Intermediate Similarity	NPC141139
0.7431	Intermediate Similarity	NPC471307
0.7431	Intermediate Similarity	NPC121872
0.7431	Intermediate Similarity	NPC78041
0.7431	Intermediate Similarity	NPC159178
0.7431	Intermediate Similarity	NPC74936
0.7431	Intermediate Similarity	NPC209764
0.7426	Intermediate Similarity	NPC197682
0.7414	Intermediate Similarity	NPC224610
0.7414	Intermediate Similarity	NPC88267
0.7414	Intermediate Similarity	NPC194390
0.7414	Intermediate Similarity	NPC113326
0.7414	Intermediate Similarity	NPC275467
0.741	Intermediate Similarity	NPC105717
0.7407	Intermediate Similarity	NPC268841
0.7407	Intermediate Similarity	NPC46098
0.7407	Intermediate Similarity	NPC307357
0.7407	Intermediate Similarity	NPC476259
0.7391	Intermediate Similarity	NPC262077
0.7372	Intermediate Similarity	NPC315283
0.7372	Intermediate Similarity	NPC314388
0.7372	Intermediate Similarity	NPC52748
0.7364	Intermediate Similarity	NPC136453
0.7357	Intermediate Similarity	NPC2501
0.7357	Intermediate Similarity	NPC129666
0.7353	Intermediate Similarity	NPC168113
0.7348	Intermediate Similarity	NPC246079
0.7345	Intermediate Similarity	NPC472258
0.7339	Intermediate Similarity	NPC470877
0.7333	Intermediate Similarity	NPC89489
0.7324	Intermediate Similarity	NPC122590
0.7324	Intermediate Similarity	NPC202198
0.7321	Intermediate Similarity	NPC58674
0.7319	Intermediate Similarity	NPC316008
0.7319	Intermediate Similarity	NPC322878
0.7319	Intermediate Similarity	NPC315266
0.7319	Intermediate Similarity	NPC313867
0.7308	Intermediate Similarity	NPC89923
0.7308	Intermediate Similarity	NPC152850
0.7308	Intermediate Similarity	NPC71933
0.7308	Intermediate Similarity	NPC239990
0.7308	Intermediate Similarity	NPC105114
0.7299	Intermediate Similarity	NPC176226
0.7288	Intermediate Similarity	NPC474804
0.7288	Intermediate Similarity	NPC130898
0.7288	Intermediate Similarity	NPC474973
0.7287	Intermediate Similarity	NPC474479
0.7287	Intermediate Similarity	NPC47667
0.728	Intermediate Similarity	NPC237420
0.7273	Intermediate Similarity	NPC172128
0.7266	Intermediate Similarity	NPC35996
0.7266	Intermediate Similarity	NPC314358
0.7254	Intermediate Similarity	NPC233702
0.7241	Intermediate Similarity	NPC329375
0.7239	Intermediate Similarity	NPC141050
0.7236	Intermediate Similarity	NPC471318
0.7232	Intermediate Similarity	NPC471309
0.7226	Intermediate Similarity	NPC469427
0.7226	Intermediate Similarity	NPC469426
0.7226	Intermediate Similarity	NPC476989
0.7222	Intermediate Similarity	NPC469903
0.7214	Intermediate Similarity	NPC329761
0.7214	Intermediate Similarity	NPC135121
0.7214	Intermediate Similarity	NPC225648
0.7214	Intermediate Similarity	NPC145113
0.7203	Intermediate Similarity	NPC476198
0.7203	Intermediate Similarity	NPC143516
0.7203	Intermediate Similarity	NPC286551
0.72	Intermediate Similarity	NPC254088
0.7194	Intermediate Similarity	NPC477217
0.7194	Intermediate Similarity	NPC201244
0.7193	Intermediate Similarity	NPC122493
0.7193	Intermediate Similarity	NPC293628
0.7193	Intermediate Similarity	NPC10781
0.7185	Intermediate Similarity	NPC474787
0.7185	Intermediate Similarity	NPC9687
0.7185	Intermediate Similarity	NPC476102
0.7185	Intermediate Similarity	NPC474811
0.7185	Intermediate Similarity	NPC474855
0.7185	Intermediate Similarity	NPC90194
0.7185	Intermediate Similarity	NPC293377
0.7185	Intermediate Similarity	NPC118099
0.7185	Intermediate Similarity	NPC273907
0.7185	Intermediate Similarity	NPC314835
0.7185	Intermediate Similarity	NPC76785
0.7185	Intermediate Similarity	NPC475598
0.7185	Intermediate Similarity	NPC260045
0.7185	Intermediate Similarity	NPC49577
0.7185	Intermediate Similarity	NPC79465
0.7185	Intermediate Similarity	NPC151706
0.7185	Intermediate Similarity	NPC475318
0.7177	Intermediate Similarity	NPC188010
0.7165	Intermediate Similarity	NPC302169
0.7165	Intermediate Similarity	NPC190663
0.7163	Intermediate Similarity	NPC471820
0.7163	Intermediate Similarity	NPC471821
0.7156	Intermediate Similarity	NPC471638
0.7154	Intermediate Similarity	NPC4974
0.7154	Intermediate Similarity	NPC474926
0.7143	Intermediate Similarity	NPC157311
0.7143	Intermediate Similarity	NPC314992
0.7133	Intermediate Similarity	NPC162104
0.7132	Intermediate Similarity	NPC43755
0.7117	Intermediate Similarity	NPC316108
0.7113	Intermediate Similarity	NPC254798
0.7113	Intermediate Similarity	NPC283783
0.7092	Intermediate Similarity	NPC311658
0.7091	Intermediate Similarity	NPC325441
0.709	Intermediate Similarity	NPC8761
0.709	Intermediate Similarity	NPC257390
0.709	Intermediate Similarity	NPC44805
0.7083	Intermediate Similarity	NPC473341
0.708	Intermediate Similarity	NPC77992
0.708	Intermediate Similarity	NPC71140

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 NPC33742 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	106
0.1-0.2	394
0.2-0.3	761
0.3-0.4	2086
0.4-0.5	3417
0.5-0.6	1758
0.6-0.7	529
0.7-0.8	94
0.8-0.85	5
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8293	Intermediate Similarity	NPD5339	Clinical (unspecified phase)
0.8264	Intermediate Similarity	NPD2584	Suspended
0.816	Intermediate Similarity	NPD4125	Approved
0.8125	Intermediate Similarity	NPD999	Phase 2
0.8	Intermediate Similarity	NPD3608	Clinical (unspecified phase)
0.7984	Intermediate Similarity	NPD7113	Clinical (unspecified phase)
0.7965	Intermediate Similarity	NPD1018	Approved
0.7934	Intermediate Similarity	NPD4504	Clinical (unspecified phase)
0.7931	Intermediate Similarity	NPD3642	Approved
0.7931	Intermediate Similarity	NPD3643	Approved
0.7931	Intermediate Similarity	NPD3644	Approved
0.7923	Intermediate Similarity	NPD8172	Phase 2
0.7923	Intermediate Similarity	NPD8173	Phase 2
0.792	Intermediate Similarity	NPD2585	Clinical (unspecified phase)
0.7857	Intermediate Similarity	NPD3604	Clinical (unspecified phase)
0.7851	Intermediate Similarity	NPD998	Approved
0.7846	Intermediate Similarity	NPD8643	Discontinued
0.784	Intermediate Similarity	NPD5577	Clinical (unspecified phase)
0.784	Intermediate Similarity	NPD5578	Approved
0.7769	Intermediate Similarity	NPD8416	Discontinued
0.7769	Intermediate Similarity	NPD4791	Clinical (unspecified phase)
0.7704	Intermediate Similarity	NPD6860	Clinical (unspecified phase)
0.7687	Intermediate Similarity	NPD7720	Phase 2
0.7686	Intermediate Similarity	NPD3123	Discovery
0.768	Intermediate Similarity	NPD3072	Approved
0.768	Intermediate Similarity	NPD3073	Approved
0.768	Intermediate Similarity	NPD3071	Approved
0.7674	Intermediate Similarity	NPD6919	Clinical (unspecified phase)
0.7652	Intermediate Similarity	NPD4782	Clinical (unspecified phase)
0.7619	Intermediate Similarity	NPD4677	Discontinued
0.7615	Intermediate Similarity	NPD6690	Approved
0.7615	Intermediate Similarity	NPD3632	Clinical (unspecified phase)
0.76	Intermediate Similarity	NPD4762	Approved
0.76	Intermediate Similarity	NPD4706	Clinical (unspecified phase)
0.76	Intermediate Similarity	NPD4761	Approved
0.7594	Intermediate Similarity	NPD6901	Phase 3
0.7591	Intermediate Similarity	NPD8323	Discontinued
0.7557	Intermediate Similarity	NPD3561	Clinical (unspecified phase)
0.7544	Intermediate Similarity	NPD4803	Discontinued
0.7537	Intermediate Similarity	NPD7728	Clinical (unspecified phase)
0.7521	Intermediate Similarity	NPD6038	Clinical (unspecified phase)
0.7519	Intermediate Similarity	NPD3626	Phase 3
0.75	Intermediate Similarity	NPD5341	Clinical (unspecified phase)
0.7464	Intermediate Similarity	NPD7602	Clinical (unspecified phase)
0.7462	Intermediate Similarity	NPD5263	Approved
0.7459	Intermediate Similarity	NPD1348	Approved
0.7456	Intermediate Similarity	NPD4760	Clinical (unspecified phase)
0.7455	Intermediate Similarity	NPD1814	Approved
0.7455	Intermediate Similarity	NPD1812	Approved
0.7438	Intermediate Similarity	NPD3598	Phase 3
0.7436	Intermediate Similarity	NPD7130	Phase 3
0.7426	Intermediate Similarity	NPD8076	Discontinued
0.7426	Intermediate Similarity	NPD4152	Approved
0.7424	Intermediate Similarity	NPD941	Approved
0.7422	Intermediate Similarity	NPD2031	Discontinued
0.7422	Intermediate Similarity	NPD3125	Approved
0.7391	Intermediate Similarity	NPD1967	Approved
0.7391	Intermediate Similarity	NPD1968	Approved
0.7385	Intermediate Similarity	NPD4177	Approved
0.7385	Intermediate Similarity	NPD4175	Approved
0.7385	Intermediate Similarity	NPD5759	Approved
0.7376	Intermediate Similarity	NPD7613	Discontinued
0.7355	Intermediate Similarity	NPD480	Approved
0.735	Intermediate Similarity	NPD5717	Approved
0.7348	Intermediate Similarity	NPD5581	Approved
0.7339	Intermediate Similarity	NPD7522	Discontinued
0.7338	Intermediate Similarity	NPD6552	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD2583	Phase 2
0.7328	Intermediate Similarity	NPD7979	Clinical (unspecified phase)
0.7328	Intermediate Similarity	NPD4676	Approved
0.7308	Intermediate Similarity	NPD4151	Approved
0.7287	Intermediate Similarity	NPD5367	Discontinued
0.7286	Intermediate Similarity	NPD8290	Clinical (unspecified phase)
0.728	Intermediate Similarity	NPD6343	Approved
0.728	Intermediate Similarity	NPD6345	Approved
0.7266	Intermediate Similarity	NPD5335	Discontinued
0.7266	Intermediate Similarity	NPD5108	Clinical (unspecified phase)
0.7259	Intermediate Similarity	NPD6073	Approved
0.7252	Intermediate Similarity	NPD3040	Approved
0.7239	Intermediate Similarity	NPD6623	Phase 3
0.7226	Intermediate Similarity	NPD6897	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD5981	Approved
0.7218	Intermediate Similarity	NPD2078	Clinical (unspecified phase)
0.7206	Intermediate Similarity	NPD6852	Discontinued
0.7203	Intermediate Similarity	NPD1040	Phase 2
0.7193	Intermediate Similarity	NPD9566	Approved
0.7165	Intermediate Similarity	NPD7342	Discontinued
0.7154	Intermediate Similarity	NPD3148	Approved
0.7154	Intermediate Similarity	NPD2658	Approved
0.7154	Intermediate Similarity	NPD6792	Phase 3
0.7154	Intermediate Similarity	NPD3150	Approved
0.7154	Intermediate Similarity	NPD6325	Discontinued
0.7154	Intermediate Similarity	NPD1036	Approved
0.7154	Intermediate Similarity	NPD3147	Approved
0.7154	Intermediate Similarity	NPD3149	Approved
0.7154	Intermediate Similarity	NPD2659	Approved
0.7153	Intermediate Similarity	NPD5301	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD2047	Approved
0.7143	Intermediate Similarity	NPD4497	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD21	Approved
0.7143	Intermediate Similarity	NPD2051	Approved
0.7143	Intermediate Similarity	NPD2045	Approved
0.7143	Intermediate Similarity	NPD2049	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD2050	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD2046	Approved
0.7143	Intermediate Similarity	NPD2044	Approved
0.7143	Intermediate Similarity	NPD2217	Approved
0.7143	Intermediate Similarity	NPD2048	Approved
0.7143	Intermediate Similarity	NPD2043	Approved
0.7143	Intermediate Similarity	NPD2218	Phase 2
0.7132	Intermediate Similarity	NPD5725	Approved
0.7122	Intermediate Similarity	NPD6681	Discovery
0.7121	Intermediate Similarity	NPD7828	Discontinued
0.712	Intermediate Similarity	NPD1344	Phase 2
0.7111	Intermediate Similarity	NPD8265	Approved
0.7111	Intermediate Similarity	NPD5296	Approved
0.7107	Intermediate Similarity	NPD3581	Discontinued
0.7094	Intermediate Similarity	NPD4119	Approved
0.7094	Intermediate Similarity	NPD5716	Approved
0.709	Intermediate Similarity	NPD1330	Phase 2
0.709	Intermediate Similarity	NPD1329	Clinical (unspecified phase)
0.709	Intermediate Similarity	NPD2846	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD7131	Phase 3
0.708	Intermediate Similarity	NPD6294	Approved
0.708	Intermediate Similarity	NPD4214	Discontinued
0.708	Intermediate Similarity	NPD6295	Approved
0.7073	Intermediate Similarity	NPD1764	Approved
0.7073	Intermediate Similarity	NPD1762	Approved
0.7068	Intermediate Similarity	NPD6359	Clinical (unspecified phase)
0.7063	Intermediate Similarity	NPD4432	Discontinued
0.7059	Intermediate Similarity	NPD3908	Approved
0.7055	Intermediate Similarity	NPD8417	Discontinued
0.705	Intermediate Similarity	NPD2022	Approved
0.705	Intermediate Similarity	NPD2088	Approved
0.705	Intermediate Similarity	NPD2087	Approved
0.704	Intermediate Similarity	NPD7508	Discontinued
0.7037	Intermediate Similarity	NPD7086	Phase 2
0.7031	Intermediate Similarity	NPD4733	Approved
0.7029	Intermediate Similarity	NPD6655	Clinical (unspecified phase)
0.7025	Intermediate Similarity	NPD2678	Approved
0.7025	Intermediate Similarity	NPD2679	Approved
0.7018	Intermediate Similarity	NPD4814	Discontinued
0.7007	Intermediate Similarity	NPD7118	Clinical (unspecified phase)
0.7007	Intermediate Similarity	NPD6817	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD2437	Approved
0.7	Intermediate Similarity	NPD3655	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD2436	Approved
0.6993	Remote Similarity	NPD6631	Clinical (unspecified phase)
0.6993	Remote Similarity	NPD2013	Approved
0.6993	Remote Similarity	NPD2014	Approved
0.6993	Remote Similarity	NPD6088	Approved
0.6993	Remote Similarity	NPD2016	Approved
0.6985	Remote Similarity	NPD5323	Approved
0.6985	Remote Similarity	NPD4153	Approved
0.6984	Remote Similarity	NPD5162	Approved
0.6983	Remote Similarity	NPD466	Approved
0.6978	Remote Similarity	NPD7511	Approved
0.6978	Remote Similarity	NPD7512	Approved
0.6977	Remote Similarity	NPD2956	Clinical (unspecified phase)
0.697	Remote Similarity	NPD6302	Clinical (unspecified phase)
0.6963	Remote Similarity	NPD5299	Approved
0.696	Remote Similarity	NPD3551	Approved
0.696	Remote Similarity	NPD747	Discontinued
0.6959	Remote Similarity	NPD7011	Discontinued
0.6957	Remote Similarity	NPD4126	Approved
0.6957	Remote Similarity	NPD4077	Clinical (unspecified phase)
0.6949	Remote Similarity	NPD854	Approved
0.6949	Remote Similarity	NPD855	Approved
0.6935	Remote Similarity	NPD2607	Approved
0.6934	Remote Similarity	NPD4757	Clinical (unspecified phase)
0.693	Remote Similarity	NPD720	Approved
0.693	Remote Similarity	NPD1080	Approved
0.693	Remote Similarity	NPD719	Approved
0.6929	Remote Similarity	NPD5990	Approved
0.6929	Remote Similarity	NPD5991	Approved
0.6923	Remote Similarity	NPD742	Approved
0.6917	Remote Similarity	NPD1766	Approved
0.6917	Remote Similarity	NPD1767	Approved
0.6917	Remote Similarity	NPD1763	Approved
0.6917	Remote Similarity	NPD1765	Approved
0.6917	Remote Similarity	NPD1761	Approved
0.6912	Remote Similarity	NPD5747	Discontinued
0.6912	Remote Similarity	NPD7634	Clinical (unspecified phase)
0.6897	Remote Similarity	NPD1099	Approved
0.6897	Remote Similarity	NPD1100	Approved
0.6897	Remote Similarity	NPD4657	Approved
0.6897	Remote Similarity	NPD4655	Approved
0.6889	Remote Similarity	NPD4794	Discontinued
0.6875	Remote Similarity	NPD7892	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD5613	Approved
0.6875	Remote Similarity	NPD5614	Approved
0.6857	Remote Similarity	NPD7450	Phase 2
0.6855	Remote Similarity	NPD753	Approved
0.685	Remote Similarity	NPD7679	Phase 2
0.6842	Remote Similarity	NPD752	Approved
0.6842	Remote Similarity	NPD3029	Clinical (unspecified phase)
0.6838	Remote Similarity	NPD4117	Approved
0.6824	Remote Similarity	NPD7267	Clinical (unspecified phase)
0.6807	Remote Similarity	NPD6027	Approved
0.6807	Remote Similarity	NPD813	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