NPASS Compound

Structure

NPC276949 OpenBabel07101718292D 32 33 0 0 1 0 0 0 0 0999 V2000 6.3196 -10.4088 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5876 -2.4088 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.1857 -9.9088 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.1857 -8.9088 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.3196 -8.4088 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.3196 -7.4088 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.4536 -6.9088 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.4536 -5.9088 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.4536 0.0912 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5876 0.5912 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.4536 -0.9088 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5876 -5.4088 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2470 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6235 0.7818 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7216 0.0912 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5876 -1.4088 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0245 -0.9749 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5876 -4.4088 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6235 0.7818 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8555 -1.4088 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7216 -0.9088 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1235 -1.4088 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.8555 -2.4088 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.7216 -3.9088 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2225 -0.9749 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9895 -2.9088 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 1.1235 -2.4088 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 3.7216 -2.9088 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 2.8555 -4.4088 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.5593 -1.5984 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.9895 -3.9088 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 3 2 0 0 0 0 2 29 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 15 1 0 0 0 0 11 16 2 0 0 0 0 12 18 1 0 0 0 0 13 14 1 0 0 0 0 13 17 1 0 0 0 0 14 19 1 0 0 0 0 15 21 2 0 0 0 0 16 21 1 0 0 0 0 17 22 1 0 0 0 0 18 24 1 0 0 0 0 19 27 1 0 0 0 0 20 21 1 0 0 0 0 22 25 1 0 0 0 0 22 28 1 6 0 0 0 23 20 1 6 0 0 0 23 26 1 0 0 0 0 23 29 1 0 0 0 0 24 29 1 0 0 0 0 24 30 2 0 0 0 0 25 27 2 0 0 0 0 25 31 1 0 0 0 0 26 28 2 3 0 0 0 26 32 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	441.3
Volume:	482.045
LogP:	4.022
LogD:	3.894
LogS:	-3.64
# 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:	0.361
Synthetic Accessibility Score:	3.237
Fsp3:	0.577
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:	-4.698
MDCK Permeability:	3.0900733690941706e-05
Pgp-inhibitor:	0.433
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.117
20% Bioavailability (F20%):	0.486
30% Bioavailability (F30%):	0.891

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.483
Plasma Protein Binding (PPB):	89.76477813720703%
Volume Distribution (VD):	0.607
Pgp-substrate:	5.241426944732666%

ADMET: Metabolism

CYP1A2-inhibitor:	0.032
CYP1A2-substrate:	0.287
CYP2C19-inhibitor:	0.623
CYP2C19-substrate:	0.424
CYP2C9-inhibitor:	0.655
CYP2C9-substrate:	0.536
CYP2D6-inhibitor:	0.181
CYP2D6-substrate:	0.35
CYP3A4-inhibitor:	0.954
CYP3A4-substrate:	0.254

ADMET: Excretion

Clearance (CL):	4.36
Half-life (T1/2):	0.58

ADMET: Toxicity

hERG Blockers:	0.027
Human Hepatotoxicity (H-HT):	0.129
Drug-inuced Liver Injury (DILI):	0.039
AMES Toxicity:	0.017
Rat Oral Acute Toxicity:	0.846
Maximum Recommended Daily Dose:	0.125
Skin Sensitization:	0.633
Carcinogencity:	0.065
Eye Corrosion:	0.003
Eye Irritation:	0.01
Respiratory Toxicity:	0.048

Download Data

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

Natural Product: NPC276949

Natural Product ID:	NPC276949
*Common Name:**	Ciliatamides A
IUPAC Name:	N-methyl-N-[(2S)-1-oxo-1-[[(3S)-2-oxoazepan-3-yl]amino]-3-phenylpropan-2-yl]dec-9-enamide
Synonyms:
Standard InCHIKey:	UNVIKJZRLTXMOH-GOTSBHOMSA-N
Standard InCHI:	InChI=1S/C26H39N3O3/c1-3-4-5-6-7-8-12-18-24(30)29(2)23(20-21-15-10-9-11-16-21)26(32)28-22-17-13-14-19-27-25(22)31/h3,9-11,15-16,22-23H,1,4-8,12-14,17-20H2,2H3,(H,27,31)(H,28,32)/t22-,23-/m0/s1
SMILES:	C=CCCCCCCCC(=O)N(C)[C@@H](Cc1ccccc1)C(=N[C@H]1CCCCN=C1O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL256144
PubChem CID:	24854116
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
Others	1

Activity Type	# Activity
Cell Line	1
Organism	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[523770]
NPT841	Organism	Leishmania major	Leishmania major	GI	=	50.0	%	PMID[523770]

☑ 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 NPC276949 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	113
0.1-0.2	1062
0.2-0.3	6879
0.3-0.4	19303
0.4-0.5	12242
0.5-0.6	2259
0.6-0.7	549
0.7-0.8	262
0.8-0.85	22
0.85-0.9	3
0.9-0.95	1
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC35850
0.9358	High Similarity	NPC33742
0.8772	High Similarity	NPC470545
0.8696	High Similarity	NPC470546
0.8684	High Similarity	NPC470544
0.8547	High Similarity	NPC200964
0.85	High Similarity	NPC101719
0.8475	Intermediate Similarity	NPC71684
0.8417	Intermediate Similarity	NPC222466
0.8362	Intermediate Similarity	NPC14672
0.8362	Intermediate Similarity	NPC285926
0.8362	Intermediate Similarity	NPC315276
0.8333	Intermediate Similarity	NPC6975
0.8293	Intermediate Similarity	NPC111428
0.8293	Intermediate Similarity	NPC473322
0.8205	Intermediate Similarity	NPC239357
0.8167	Intermediate Similarity	NPC202521
0.816	Intermediate Similarity	NPC255447
0.8083	Intermediate Similarity	NPC476990
0.8073	Intermediate Similarity	NPC12730
0.8018	Intermediate Similarity	NPC471317
0.8017	Intermediate Similarity	NPC474584
0.7969	Intermediate Similarity	NPC248283
0.7967	Intermediate Similarity	NPC22746
0.7965	Intermediate Similarity	NPC45033
0.7963	Intermediate Similarity	NPC25565
0.7951	Intermediate Similarity	NPC252878
0.7937	Intermediate Similarity	NPC200589
0.792	Intermediate Similarity	NPC319766
0.789	Intermediate Similarity	NPC473501
0.789	Intermediate Similarity	NPC475439
0.7886	Intermediate Similarity	NPC175726
0.7886	Intermediate Similarity	NPC474082
0.7886	Intermediate Similarity	NPC46427
0.7874	Intermediate Similarity	NPC130309
0.7857	Intermediate Similarity	NPC164859
0.7845	Intermediate Similarity	NPC319579
0.7818	Intermediate Similarity	NPC322598
0.7807	Intermediate Similarity	NPC327481
0.7795	Intermediate Similarity	NPC300315
0.7786	Intermediate Similarity	NPC132636
0.7769	Intermediate Similarity	NPC220698
0.7706	Intermediate Similarity	NPC161972
0.7706	Intermediate Similarity	NPC303045
0.7686	Intermediate Similarity	NPC169328
0.7674	Intermediate Similarity	NPC325479
0.7669	Intermediate Similarity	NPC263493
0.7669	Intermediate Similarity	NPC269398
0.7627	Intermediate Similarity	NPC329011
0.7623	Intermediate Similarity	NPC310467
0.7615	Intermediate Similarity	NPC287401
0.7612	Intermediate Similarity	NPC139326
0.7612	Intermediate Similarity	NPC161069
0.7593	Intermediate Similarity	NPC226438
0.7578	Intermediate Similarity	NPC469666
0.7576	Intermediate Similarity	NPC471264
0.7576	Intermediate Similarity	NPC68865
0.7576	Intermediate Similarity	NPC471265
0.7568	Intermediate Similarity	NPC311242
0.7565	Intermediate Similarity	NPC67043
0.7565	Intermediate Similarity	NPC473418
0.7559	Intermediate Similarity	NPC477937
0.7556	Intermediate Similarity	NPC476978
0.7544	Intermediate Similarity	NPC202613
0.7521	Intermediate Similarity	NPC197470
0.7519	Intermediate Similarity	NPC178662
0.7519	Intermediate Similarity	NPC476133
0.7519	Intermediate Similarity	NPC92784
0.7519	Intermediate Similarity	NPC470884
0.7519	Intermediate Similarity	NPC98424
0.75	Intermediate Similarity	NPC471307
0.75	Intermediate Similarity	NPC478016
0.75	Intermediate Similarity	NPC74936
0.75	Intermediate Similarity	NPC159178
0.75	Intermediate Similarity	NPC78041
0.75	Intermediate Similarity	NPC209764
0.75	Intermediate Similarity	NPC141139
0.75	Intermediate Similarity	NPC5620
0.75	Intermediate Similarity	NPC478014
0.75	Intermediate Similarity	NPC478015
0.75	Intermediate Similarity	NPC121872
0.75	Intermediate Similarity	NPC209509
0.7481	Intermediate Similarity	NPC197682
0.7478	Intermediate Similarity	NPC224610
0.7478	Intermediate Similarity	NPC88267
0.7478	Intermediate Similarity	NPC113326
0.7478	Intermediate Similarity	NPC194390
0.7463	Intermediate Similarity	NPC307357
0.7463	Intermediate Similarity	NPC239762
0.7463	Intermediate Similarity	NPC476259
0.7463	Intermediate Similarity	NPC46098
0.7463	Intermediate Similarity	NPC163392
0.7463	Intermediate Similarity	NPC268841
0.7444	Intermediate Similarity	NPC127741
0.7407	Intermediate Similarity	NPC470877
0.7407	Intermediate Similarity	NPC168113
0.7405	Intermediate Similarity	NPC246079
0.7391	Intermediate Similarity	NPC138775
0.7391	Intermediate Similarity	NPC16188
0.7388	Intermediate Similarity	NPC313694
0.7388	Intermediate Similarity	NPC242159
0.7387	Intermediate Similarity	NPC58674
0.736	Intermediate Similarity	NPC27833
0.7353	Intermediate Similarity	NPC176226
0.735	Intermediate Similarity	NPC474804
0.735	Intermediate Similarity	NPC474973
0.735	Intermediate Similarity	NPC130898
0.7339	Intermediate Similarity	NPC237420
0.7338	Intermediate Similarity	NPC105717
0.7304	Intermediate Similarity	NPC329375
0.7299	Intermediate Similarity	NPC52748
0.7299	Intermediate Similarity	NPC314388
0.7299	Intermediate Similarity	NPC315283
0.7297	Intermediate Similarity	NPC471309
0.7295	Intermediate Similarity	NPC471318
0.7287	Intermediate Similarity	NPC136453
0.7286	Intermediate Similarity	NPC129666
0.7286	Intermediate Similarity	NPC2501
0.7279	Intermediate Similarity	NPC469426
0.7279	Intermediate Similarity	NPC469427
0.7266	Intermediate Similarity	NPC145113
0.7266	Intermediate Similarity	NPC135121
0.7266	Intermediate Similarity	NPC225648
0.7266	Intermediate Similarity	NPC329761
0.7265	Intermediate Similarity	NPC476198
0.7265	Intermediate Similarity	NPC143516
0.7259	Intermediate Similarity	NPC122553
0.7259	Intermediate Similarity	NPC89489
0.7258	Intermediate Similarity	NPC254088
0.7257	Intermediate Similarity	NPC10781
0.7257	Intermediate Similarity	NPC293628
0.7257	Intermediate Similarity	NPC122493
0.7246	Intermediate Similarity	NPC201244
0.7246	Intermediate Similarity	NPC322878
0.7246	Intermediate Similarity	NPC477217
0.7246	Intermediate Similarity	NPC313867
0.7246	Intermediate Similarity	NPC315266
0.7246	Intermediate Similarity	NPC316008
0.7246	Intermediate Similarity	NPC471680
0.7236	Intermediate Similarity	NPC188010
0.7231	Intermediate Similarity	NPC152850
0.7231	Intermediate Similarity	NPC71933
0.7231	Intermediate Similarity	NPC105114
0.7231	Intermediate Similarity	NPC239990
0.7231	Intermediate Similarity	NPC89923
0.7222	Intermediate Similarity	NPC190663
0.7222	Intermediate Similarity	NPC471638
0.7209	Intermediate Similarity	NPC47667
0.7203	Intermediate Similarity	NPC473498
0.72	Intermediate Similarity	NPC314992
0.7194	Intermediate Similarity	NPC314358
0.7194	Intermediate Similarity	NPC262077
0.7188	Intermediate Similarity	NPC35996
0.7183	Intermediate Similarity	NPC233702
0.7182	Intermediate Similarity	NPC316108
0.7182	Intermediate Similarity	NPC172128
0.7164	Intermediate Similarity	NPC141050
0.7156	Intermediate Similarity	NPC325441
0.7143	Intermediate Similarity	NPC71140
0.7133	Intermediate Similarity	NPC122590
0.7133	Intermediate Similarity	NPC202198
0.7133	Intermediate Similarity	NPC286551
0.7113	Intermediate Similarity	NPC324081
0.7111	Intermediate Similarity	NPC314835
0.7109	Intermediate Similarity	NPC160493
0.7105	Intermediate Similarity	NPC324569
0.7101	Intermediate Similarity	NPC468984
0.7092	Intermediate Similarity	NPC471821
0.7092	Intermediate Similarity	NPC471820
0.7087	Intermediate Similarity	NPC302169
0.7087	Intermediate Similarity	NPC80150
0.708	Intermediate Similarity	NPC256452
0.7077	Intermediate Similarity	NPC4974
0.7071	Intermediate Similarity	NPC81026
0.7068	Intermediate Similarity	NPC157311
0.7063	Intermediate Similarity	NPC162104
0.7059	Intermediate Similarity	NPC471447
0.7059	Intermediate Similarity	NPC43755
0.7054	Intermediate Similarity	NPC323164
0.7042	Intermediate Similarity	NPC283783
0.7042	Intermediate Similarity	NPC254798
0.704	Intermediate Similarity	NPC2265
0.7034	Intermediate Similarity	NPC275467
0.7034	Intermediate Similarity	NPC469903
0.7029	Intermediate Similarity	NPC476989
0.7027	Intermediate Similarity	NPC258627
0.7021	Intermediate Similarity	NPC311658
0.7015	Intermediate Similarity	NPC257390
0.7015	Intermediate Similarity	NPC8761
0.7015	Intermediate Similarity	NPC44805
0.7	Intermediate Similarity	NPC266741
0.7	Intermediate Similarity	NPC12429
0.6985	Remote Similarity	NPC475318
0.6985	Remote Similarity	NPC76785
0.6985	Remote Similarity	NPC9687
0.6985	Remote Similarity	NPC49577
0.6985	Remote Similarity	NPC474855
0.6985	Remote Similarity	NPC474811
0.6985	Remote Similarity	NPC118099
0.6985	Remote Similarity	NPC475598

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 NPC276949 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	105
0.1-0.2	395
0.2-0.3	814
0.3-0.4	2236
0.4-0.5	3397
0.5-0.6	1611
0.6-0.7	511
0.7-0.8	79
0.8-0.85	2
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8211	Intermediate Similarity	NPD3608	Clinical (unspecified phase)
0.8182	Intermediate Similarity	NPD2584	Suspended
0.808	Intermediate Similarity	NPD4125	Approved
0.8065	Intermediate Similarity	NPD5339	Clinical (unspecified phase)
0.7907	Intermediate Similarity	NPD7113	Clinical (unspecified phase)
0.7851	Intermediate Similarity	NPD4504	Clinical (unspecified phase)
0.7846	Intermediate Similarity	NPD8172	Phase 2
0.7846	Intermediate Similarity	NPD8173	Phase 2
0.7845	Intermediate Similarity	NPD3644	Approved
0.7845	Intermediate Similarity	NPD3643	Approved
0.7845	Intermediate Similarity	NPD3642	Approved
0.784	Intermediate Similarity	NPD2585	Clinical (unspecified phase)
0.7829	Intermediate Similarity	NPD8416	Discontinued
0.7769	Intermediate Similarity	NPD8643	Discontinued
0.775	Intermediate Similarity	NPD3123	Discovery
0.7734	Intermediate Similarity	NPD6919	Clinical (unspecified phase)
0.7717	Intermediate Similarity	NPD3626	Phase 3
0.7692	Intermediate Similarity	NPD4791	Clinical (unspecified phase)
0.7685	Intermediate Similarity	NPD6690	Approved
0.7615	Intermediate Similarity	NPD3561	Clinical (unspecified phase)
0.7612	Intermediate Similarity	NPD7720	Phase 2
0.76	Intermediate Similarity	NPD3072	Approved
0.76	Intermediate Similarity	NPD3071	Approved
0.76	Intermediate Similarity	NPD3073	Approved
0.7576	Intermediate Similarity	NPD4782	Clinical (unspecified phase)
0.7565	Intermediate Similarity	NPD999	Phase 2
0.754	Intermediate Similarity	NPD4677	Discontinued
0.7538	Intermediate Similarity	NPD3632	Clinical (unspecified phase)
0.7523	Intermediate Similarity	NPD1812	Approved
0.7523	Intermediate Similarity	NPD1814	Approved
0.7522	Intermediate Similarity	NPD4760	Clinical (unspecified phase)
0.7521	Intermediate Similarity	NPD1348	Approved
0.752	Intermediate Similarity	NPD4762	Approved
0.752	Intermediate Similarity	NPD4761	Approved
0.752	Intermediate Similarity	NPD4706	Clinical (unspecified phase)
0.7519	Intermediate Similarity	NPD6901	Phase 3
0.75	Intermediate Similarity	NPD3604	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD6860	Clinical (unspecified phase)
0.748	Intermediate Similarity	NPD998	Approved
0.7456	Intermediate Similarity	NPD4803	Discontinued
0.7436	Intermediate Similarity	NPD6038	Clinical (unspecified phase)
0.7417	Intermediate Similarity	NPD480	Approved
0.7414	Intermediate Similarity	NPD1018	Approved
0.7391	Intermediate Similarity	NPD7602	Clinical (unspecified phase)
0.7391	Intermediate Similarity	NPD8323	Discontinued
0.7391	Intermediate Similarity	NPD6552	Clinical (unspecified phase)
0.7385	Intermediate Similarity	NPD7979	Clinical (unspecified phase)
0.7355	Intermediate Similarity	NPD3598	Phase 3
0.7353	Intermediate Similarity	NPD8076	Discontinued
0.735	Intermediate Similarity	NPD7130	Phase 3
0.7344	Intermediate Similarity	NPD5577	Clinical (unspecified phase)
0.7344	Intermediate Similarity	NPD5578	Approved
0.7344	Intermediate Similarity	NPD5367	Discontinued
0.7344	Intermediate Similarity	NPD3125	Approved
0.7333	Intermediate Similarity	NPD7728	Clinical (unspecified phase)
0.7308	Intermediate Similarity	NPD4177	Approved
0.7308	Intermediate Similarity	NPD3040	Approved
0.7308	Intermediate Similarity	NPD4175	Approved
0.7299	Intermediate Similarity	NPD5341	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD5581	Approved
0.7265	Intermediate Similarity	NPD5717	Approved
0.7265	Intermediate Similarity	NPD1040	Phase 2
0.7258	Intermediate Similarity	NPD7522	Discontinued
0.7257	Intermediate Similarity	NPD9566	Approved
0.7252	Intermediate Similarity	NPD4676	Approved
0.7252	Intermediate Similarity	NPD5263	Approved
0.7231	Intermediate Similarity	NPD4151	Approved
0.7222	Intermediate Similarity	NPD7342	Discontinued
0.72	Intermediate Similarity	NPD2218	Phase 2
0.72	Intermediate Similarity	NPD6343	Approved
0.72	Intermediate Similarity	NPD2217	Approved
0.72	Intermediate Similarity	NPD6345	Approved
0.7197	Intermediate Similarity	NPD2050	Clinical (unspecified phase)
0.7197	Intermediate Similarity	NPD2043	Approved
0.7197	Intermediate Similarity	NPD2044	Approved
0.7197	Intermediate Similarity	NPD2051	Approved
0.7197	Intermediate Similarity	NPD2046	Approved
0.7197	Intermediate Similarity	NPD2045	Approved
0.7197	Intermediate Similarity	NPD2047	Approved
0.7197	Intermediate Similarity	NPD2048	Approved
0.7197	Intermediate Similarity	NPD2049	Clinical (unspecified phase)
0.7197	Intermediate Similarity	NPD21	Approved
0.7188	Intermediate Similarity	NPD5108	Clinical (unspecified phase)
0.7188	Intermediate Similarity	NPD5335	Discontinued
0.7183	Intermediate Similarity	NPD7613	Discontinued
0.7177	Intermediate Similarity	NPD1344	Phase 2
0.7176	Intermediate Similarity	NPD5759	Approved
0.7164	Intermediate Similarity	NPD6623	Phase 3
0.7143	Intermediate Similarity	NPD2078	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD5981	Approved
0.7132	Intermediate Similarity	NPD6852	Discontinued
0.7132	Intermediate Similarity	NPD4214	Discontinued
0.7113	Intermediate Similarity	NPD4432	Discontinued
0.7101	Intermediate Similarity	NPD2088	Approved
0.7101	Intermediate Similarity	NPD2087	Approved
0.7101	Intermediate Similarity	NPD2022	Approved
0.7101	Intermediate Similarity	NPD4152	Approved
0.7092	Intermediate Similarity	NPD8290	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD2679	Approved
0.7083	Intermediate Similarity	NPD2678	Approved
0.708	Intermediate Similarity	NPD4814	Discontinued
0.708	Intermediate Similarity	NPD5301	Clinical (unspecified phase)
0.7077	Intermediate Similarity	NPD6792	Phase 3
0.7077	Intermediate Similarity	NPD2031	Discontinued
0.7077	Intermediate Similarity	NPD6325	Discontinued
0.7073	Intermediate Similarity	NPD2658	Approved
0.7073	Intermediate Similarity	NPD3149	Approved
0.7073	Intermediate Similarity	NPD3148	Approved
0.7073	Intermediate Similarity	NPD2659	Approved
0.7073	Intermediate Similarity	NPD3150	Approved
0.7073	Intermediate Similarity	NPD3147	Approved
0.7071	Intermediate Similarity	NPD1967	Approved
0.7071	Intermediate Similarity	NPD1968	Approved
0.7068	Intermediate Similarity	NPD4497	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD6073	Approved
0.7059	Intermediate Similarity	NPD5725	Approved
0.705	Intermediate Similarity	NPD2437	Approved
0.705	Intermediate Similarity	NPD2436	Approved
0.705	Intermediate Similarity	NPD6681	Discovery
0.7045	Intermediate Similarity	NPD7828	Discontinued
0.7043	Intermediate Similarity	NPD466	Approved
0.704	Intermediate Similarity	NPD5162	Approved
0.7037	Intermediate Similarity	NPD8265	Approved
0.7037	Intermediate Similarity	NPD5296	Approved
0.7037	Intermediate Similarity	NPD5323	Approved
0.7037	Intermediate Similarity	NPD4153	Approved
0.7029	Intermediate Similarity	NPD6897	Clinical (unspecified phase)
0.7025	Intermediate Similarity	NPD3581	Discontinued
0.7015	Intermediate Similarity	NPD2846	Clinical (unspecified phase)
0.7015	Intermediate Similarity	NPD5299	Approved
0.7015	Intermediate Similarity	NPD1330	Phase 2
0.7015	Intermediate Similarity	NPD1329	Clinical (unspecified phase)
0.7014	Intermediate Similarity	NPD7131	Phase 3
0.7009	Intermediate Similarity	NPD4119	Approved
0.7009	Intermediate Similarity	NPD5716	Approved
0.7009	Intermediate Similarity	NPD854	Approved
0.7009	Intermediate Similarity	NPD855	Approved
0.7007	Intermediate Similarity	NPD6295	Approved
0.7007	Intermediate Similarity	NPD6294	Approved
0.6992	Remote Similarity	NPD1762	Approved
0.6992	Remote Similarity	NPD1764	Approved
0.6992	Remote Similarity	NPD6359	Clinical (unspecified phase)
0.6991	Remote Similarity	NPD1080	Approved
0.6985	Remote Similarity	NPD4757	Clinical (unspecified phase)
0.6983	Remote Similarity	NPD742	Approved
0.6975	Remote Similarity	NPD1767	Approved
0.6975	Remote Similarity	NPD1763	Approved
0.6975	Remote Similarity	NPD1766	Approved
0.6975	Remote Similarity	NPD1765	Approved
0.6975	Remote Similarity	NPD1761	Approved
0.6967	Remote Similarity	NPD2583	Phase 2
0.6963	Remote Similarity	NPD941	Approved
0.6963	Remote Similarity	NPD7086	Phase 2
0.696	Remote Similarity	NPD7508	Discontinued
0.6957	Remote Similarity	NPD1099	Approved
0.6957	Remote Similarity	NPD1100	Approved
0.6957	Remote Similarity	NPD6655	Clinical (unspecified phase)
0.6953	Remote Similarity	NPD4733	Approved
0.6939	Remote Similarity	NPD7118	Clinical (unspecified phase)
0.6934	Remote Similarity	NPD6817	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD6088	Approved
0.6923	Remote Similarity	NPD6631	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD7892	Clinical (unspecified phase)
0.6911	Remote Similarity	NPD753	Approved
0.6899	Remote Similarity	NPD2956	Clinical (unspecified phase)
0.6894	Remote Similarity	NPD6302	Clinical (unspecified phase)
0.6892	Remote Similarity	NPD6725	Clinical (unspecified phase)
0.6892	Remote Similarity	NPD6726	Phase 2
0.6884	Remote Similarity	NPD4077	Clinical (unspecified phase)
0.6884	Remote Similarity	NPD4126	Approved
0.688	Remote Similarity	NPD747	Discontinued
0.688	Remote Similarity	NPD3551	Approved
0.6871	Remote Similarity	NPD8417	Discontinued
0.6864	Remote Similarity	NPD813	Approved
0.6861	Remote Similarity	NPD3908	Approved
0.6855	Remote Similarity	NPD3066	Phase 2
0.6855	Remote Similarity	NPD2607	Approved
0.6855	Remote Similarity	NPD4165	Phase 2
0.685	Remote Similarity	NPD5991	Approved
0.685	Remote Similarity	NPD5990	Approved
0.6846	Remote Similarity	NPD7599	Phase 2
0.6842	Remote Similarity	NPD3588	Discontinued
0.6842	Remote Similarity	NPD1066	Discontinued
0.6838	Remote Similarity	NPD7634	Clinical (unspecified phase)
0.6838	Remote Similarity	NPD5747	Discontinued
0.6835	Remote Similarity	NPD4158	Clinical (unspecified phase)
0.6835	Remote Similarity	NPD3480	Approved
0.6818	Remote Similarity	NPD2634	Clinical (unspecified phase)
0.6815	Remote Similarity	NPD4794	Discontinued
0.6815	Remote Similarity	NPD4738	Phase 2
0.681	Remote Similarity	NPD4655	Approved
0.681	Remote Similarity	NPD4657	Approved
0.6806	Remote Similarity	NPD3987	Approved
0.6806	Remote Similarity	NPD3988	Approved
0.6806	Remote Similarity	NPD5613	Approved
0.6806	Remote Similarity	NPD5614	Approved
0.68	Remote Similarity	NPD7600	Phase 2
0.6797	Remote Similarity	NPD6093	Discontinued
0.6786	Remote Similarity	NPD7450	Phase 2
0.6786	Remote Similarity	NPD7511	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