NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	1029.56
Volume:	1015.019
LogP:	-0.543
LogD:	1.097
LogS:	-0.806
# Rotatable Bonds:	23
TPSA:	438.85
# H-Bond Aceptor:	26
# H-Bond Donor:	15
# Rings:	1
# Heavy Atoms:	26

MedChem Properties

QED Drug-Likeness Score:	0.03
Synthetic Accessibility Score:	6.941
Fsp3:	0.761
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	2
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.474
MDCK Permeability:	0.00039054383523762226
Pgp-inhibitor:	0.556
Pgp-substrate:	1.0
Human Intestinal Absorption (HIA):	0.999
20% Bioavailability (F20%):	0.997
30% Bioavailability (F30%):	0.999

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.258
Plasma Protein Binding (PPB):	22.530517578125%
Volume Distribution (VD):	0.37
Pgp-substrate:	57.988868713378906%

ADMET: Metabolism

CYP1A2-inhibitor:	0.0
CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.002
CYP2C19-substrate:	0.02
CYP2C9-inhibitor:	0.001
CYP2C9-substrate:	0.055
CYP2D6-inhibitor:	0.0
CYP2D6-substrate:	0.019
CYP3A4-inhibitor:	0.027
CYP3A4-substrate:	0.0

ADMET: Excretion

Clearance (CL):	1.903
Half-life (T1/2):	0.797

ADMET: Toxicity

hERG Blockers:	0.0
Human Hepatotoxicity (H-HT):	1.0
Drug-inuced Liver Injury (DILI):	0.852
AMES Toxicity:	0.003
Rat Oral Acute Toxicity:	0.0
Maximum Recommended Daily Dose:	0.003
Skin Sensitization:	0.714
Carcinogencity:	0.079
Eye Corrosion:	0.003
Eye Irritation:	0.017
Respiratory Toxicity:	0.942

Download Data

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

Natural Product: NPC477729

Natural Product ID:	NPC477729
*Common Name:**	3-[(6R,9R,12S,18S,24S)-9-(2-amino-2-oxo-ethyl)-6-[(1S)-1-hydroxyethyl]-3,21-bis(2-hydroxyethyl)-12-(hydroxymethyl)-24-methyl-28-(1-methyltridecyl)-2,5,8,11,14,17,20,23,26-nonaoxo-1-oxa-4,7,10,13,16,19,22,25-octazacyclooctacos-18-yl]propanoic acid
IUPAC Name:	3-[(6R,9R,12S,18S,24S)-9-(2-amino-2-oxoethyl)-6-[(1S)-1-hydroxyethyl]-3,21-bis(2-hydroxyethyl)-12-(hydroxymethyl)-24-methyl-2,5,8,11,14,17,20,23,26-nonaoxo-28-tetradecan-2-yl-1-oxa-4,7,10,13,16,19,22,25-octazacyclooctacos-18-yl]propanoic acid
Synonyms:	Phomafungin
Standard InCHIKey:	YCYMGGDRXJWJAS-LXZOVAIASA-N
Standard InCHI:	InChI=1S/C46H79N9O17/c1-5-6-7-8-9-10-11-12-13-14-15-26(2)34-23-36(61)49-27(3)40(65)51-30(18-20-56)42(67)52-29(16-17-38(63)64)41(66)48-24-37(62)50-33(25-58)44(69)54-32(22-35(47)60)43(68)55-39(28(4)59)45(70)53-31(19-21-57)46(71)72-34/h26-34,39,56-59H,5-25H2,1-4H3,(H2,47,60)(H,48,66)(H,49,61)(H,50,62)(H,51,65)(H,52,67)(H,53,70)(H,54,69)(H,55,68)(H,63,64)/t26?,27-,28-,29-,30?,31?,32+,33-,34?,39+/m0/s1
SMILES:	CCCCCCCCCCCCC(C)C1CC(=O)N[C@H](C(=O)NC(C(=O)N[C@H](C(=O)NCC(=O)N[C@H](C(=O)N[C@@H](C(=O)N[C@@H](C(=O)NC(C(=O)O1)CCO)[C@H](C)O)CC(=O)N)CO)CCC(=O)O)CCO)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	n.a.
PubChem CID:	25242460
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000264] Organic acids and derivatives [CHEMONTID:0001813] Peptidomimetics [CHEMONTID:0001961] Depsipeptides [CHEMONTID:0001994] Cyclic depsipeptides

*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
NPO32545	Phaeosphaeria sp.	Species	Phaeosphaeriaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18570471]
NPO32545	Phaeosphaeria sp.	Species	Phaeosphaeriaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22276650]
NPO32545	Phaeosphaeria sp.	Species	Phaeosphaeriaceae	Eukaryota	isolated from living stems and leaves of a Sedum sp.	Motilleja, Albacete, Spain	n.a.	PMID[23259972]

☑ 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	4
Others	13

Activity Type	# Activity
Cell Line	3
Organism	13
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT393	Cell Line	HCT-116	Homo sapiens	IC50	=	20000	nM	PMID[19112025]
NPT306	Cell Line	PC-3	Homo sapiens	IC50	=	19000	nM	PMID[19112025]
NPT2192	Cell Line	HEL	Homo sapiens	IC50	=	15500	nM	PMID[19112025]
NPT27	Others	Unspecified		IC50	=	26000	nM	PMID[19112025]
NPT330	Organism	Trichophyton mentagrophytes	Trichophyton mentagrophytes	MIC80	=	1	ug/ml	PMID[19112025]
NPT330	Organism	Trichophyton mentagrophytes	Trichophyton mentagrophytes	MIC100	=	2	ug/ml	PMID[19112025]
NPT20	Organism	Candida albicans	Candida albicans	MIC100	=	4	ug/ml	PMID[19112025]
NPT554	Organism	Candida glabrata	Candida glabrata	MIC80	=	4	ug/ml	PMID[19112025]
NPT188	Organism	Candida parapsilosis	Candida parapsilosis	MIC100	=	4	ug/ml	PMID[19112025]
NPT820	Organism	Clavispora lusitaniae	Clavispora lusitaniae	MIC100	=	4	ug/ml	PMID[19112025]
NPT187	Organism	Issatchenkia orientalis	Pichia kudriavzevii	MIC100	=	4	ug/ml	PMID[19112025]
NPT87	Organism	Aspergillus fumigatus	Aspergillus fumigatus	MIC100	=	4	ug/ml	PMID[19112025]
NPT554	Organism	Candida glabrata	Candida glabrata	MIC100	=	8	ug/ml	PMID[19112025]
NPT20	Organism	Candida albicans	Candida albicans	MIC100	>	32	ug/ml	PMID[19112025]
NPT186	Organism	Candida tropicalis	Candida tropicalis	MIC100	>	32	ug/ml	PMID[19112025]
NPT87	Organism	Aspergillus fumigatus	Aspergillus fumigatus	MIC100	>	32	ug/ml	PMID[19112025]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC100	>	32	ug/ml	PMID[19112025]

☑ 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 NPC477729 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	124
0.1-0.2	2493
0.2-0.3	21094
0.3-0.4	14429
0.4-0.5	3843
0.5-0.6	521
0.6-0.7	118
0.7-0.8	43
0.8-0.85	9
0.85-0.9	6
0.9-0.95	14
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9167	High Similarity	NPC227051
0.9048	High Similarity	NPC155670
0.9048	High Similarity	NPC95478
0.9048	High Similarity	NPC145748
0.8193	Intermediate Similarity	NPC86064
0.8111	Intermediate Similarity	NPC477728
0.8072	Intermediate Similarity	NPC43219
0.7865	Intermediate Similarity	NPC477730
0.7816	Intermediate Similarity	NPC478017
0.7816	Intermediate Similarity	NPC315535
0.7816	Intermediate Similarity	NPC315131
0.7711	Intermediate Similarity	NPC478256
0.7701	Intermediate Similarity	NPC316242
0.7582	Intermediate Similarity	NPC320936
0.747	Intermediate Similarity	NPC470110
0.7416	Intermediate Similarity	NPC473984
0.7349	Intermediate Similarity	NPC470109
0.7297	Intermediate Similarity	NPC477237
0.7273	Intermediate Similarity	NPC476130
0.7273	Intermediate Similarity	NPC476324
0.7253	Intermediate Similarity	NPC314466
0.7241	Intermediate Similarity	NPC138435
0.7229	Intermediate Similarity	NPC470108
0.7176	Intermediate Similarity	NPC475808
0.7176	Intermediate Similarity	NPC474298
0.7176	Intermediate Similarity	NPC28348
0.7176	Intermediate Similarity	NPC472579
0.7176	Intermediate Similarity	NPC473985
0.7176	Intermediate Similarity	NPC474299
0.7168	Intermediate Similarity	NPC477238
0.7143	Intermediate Similarity	NPC270005
0.7143	Intermediate Similarity	NPC208537
0.7126	Intermediate Similarity	NPC141325
0.7097	Intermediate Similarity	NPC47135
0.7	Intermediate Similarity	NPC470283
0.6893	Remote Similarity	NPC220234
0.6786	Remote Similarity	NPC471645
0.6782	Remote Similarity	NPC314273
0.6782	Remote Similarity	NPC193280
0.6705	Remote Similarity	NPC476285
0.6705	Remote Similarity	NPC476291
0.6667	Remote Similarity	NPC476248
0.6667	Remote Similarity	NPC195165
0.6667	Remote Similarity	NPC193386
0.663	Remote Similarity	NPC472594
0.6629	Remote Similarity	NPC477200
0.6598	Remote Similarity	NPC476523
0.6556	Remote Similarity	NPC320865
0.6556	Remote Similarity	NPC474403
0.6556	Remote Similarity	NPC477641
0.6556	Remote Similarity	NPC477643
0.6542	Remote Similarity	NPC301148
0.6542	Remote Similarity	NPC124554
0.6542	Remote Similarity	NPC5864
0.6517	Remote Similarity	NPC477642
0.65	Remote Similarity	NPC470284
0.6471	Remote Similarity	NPC315237
0.6471	Remote Similarity	NPC327252
0.6458	Remote Similarity	NPC53858
0.6458	Remote Similarity	NPC84128
0.6436	Remote Similarity	NPC159369
0.6436	Remote Similarity	NPC39290
0.6422	Remote Similarity	NPC124549
0.6413	Remote Similarity	NPC472595
0.6408	Remote Similarity	NPC226513
0.6404	Remote Similarity	NPC471202
0.6404	Remote Similarity	NPC63191
0.6396	Remote Similarity	NPC67009
0.6386	Remote Similarity	NPC472578
0.6383	Remote Similarity	NPC37681
0.6381	Remote Similarity	NPC160066
0.6364	Remote Similarity	NPC241394
0.6364	Remote Similarity	NPC475918
0.6356	Remote Similarity	NPC470652
0.6353	Remote Similarity	NPC477644
0.6337	Remote Similarity	NPC292345
0.633	Remote Similarity	NPC198344
0.6281	Remote Similarity	NPC470650
0.6281	Remote Similarity	NPC470653
0.6281	Remote Similarity	NPC470654
0.6273	Remote Similarity	NPC128303
0.6262	Remote Similarity	NPC475440
0.626	Remote Similarity	NPC477793
0.626	Remote Similarity	NPC329919
0.625	Remote Similarity	NPC171734
0.6239	Remote Similarity	NPC227622
0.6235	Remote Similarity	NPC327170
0.6235	Remote Similarity	NPC329564
0.6224	Remote Similarity	NPC474312
0.6147	Remote Similarity	NPC188453
0.6147	Remote Similarity	NPC42320
0.6126	Remote Similarity	NPC74035
0.6118	Remote Similarity	NPC317143
0.6118	Remote Similarity	NPC473599
0.6118	Remote Similarity	NPC321536
0.6118	Remote Similarity	NPC321468
0.6118	Remote Similarity	NPC316826
0.6118	Remote Similarity	NPC327748
0.6106	Remote Similarity	NPC15413
0.6102	Remote Similarity	NPC329216
0.6102	Remote Similarity	NPC209734
0.6092	Remote Similarity	NPC145627
0.6078	Remote Similarity	NPC470282
0.6075	Remote Similarity	NPC47076
0.6075	Remote Similarity	NPC134504
0.6071	Remote Similarity	NPC317147
0.6071	Remote Similarity	NPC318260
0.6047	Remote Similarity	NPC143722
0.6044	Remote Similarity	NPC126779
0.604	Remote Similarity	NPC83839
0.6033	Remote Similarity	NPC315188
0.6033	Remote Similarity	NPC160688
0.6032	Remote Similarity	NPC313657
0.6024	Remote Similarity	NPC322573
0.6023	Remote Similarity	NPC145658
0.6017	Remote Similarity	NPC296043
0.6	Remote Similarity	NPC190385
0.6	Remote Similarity	NPC470651
0.6	Remote Similarity	NPC62263
0.6	Remote Similarity	NPC470655
0.6	Remote Similarity	NPC471098
0.6	Remote Similarity	NPC173763
0.5982	Remote Similarity	NPC14537
0.5982	Remote Similarity	NPC323720
0.5966	Remote Similarity	NPC201968
0.5962	Remote Similarity	NPC474593
0.5962	Remote Similarity	NPC475801
0.5948	Remote Similarity	NPC476875
0.5941	Remote Similarity	NPC125253
0.5941	Remote Similarity	NPC192025
0.5941	Remote Similarity	NPC253975
0.5929	Remote Similarity	NPC475637
0.5929	Remote Similarity	NPC473252
0.5905	Remote Similarity	NPC474576
0.5889	Remote Similarity	NPC474402
0.5882	Remote Similarity	NPC470621
0.5882	Remote Similarity	NPC222481
0.5877	Remote Similarity	NPC137453
0.5865	Remote Similarity	NPC322966
0.5862	Remote Similarity	NPC471129
0.5851	Remote Similarity	NPC55274
0.5826	Remote Similarity	NPC475150
0.5826	Remote Similarity	NPC70235
0.5818	Remote Similarity	NPC234542
0.5818	Remote Similarity	NPC474952
0.5816	Remote Similarity	NPC474833
0.5804	Remote Similarity	NPC477198
0.58	Remote Similarity	NPC246005
0.5798	Remote Similarity	NPC50694
0.5798	Remote Similarity	NPC259586
0.5784	Remote Similarity	NPC477199
0.578	Remote Similarity	NPC313821
0.578	Remote Similarity	NPC189629
0.5776	Remote Similarity	NPC329305
0.5776	Remote Similarity	NPC473578
0.5766	Remote Similarity	NPC473224
0.5765	Remote Similarity	NPC38463
0.5765	Remote Similarity	NPC325985
0.5763	Remote Similarity	NPC76660
0.5763	Remote Similarity	NPC276995
0.5758	Remote Similarity	NPC474702
0.5747	Remote Similarity	NPC254541
0.5747	Remote Similarity	NPC320598
0.5726	Remote Similarity	NPC273185
0.5714	Remote Similarity	NPC477145
0.5714	Remote Similarity	NPC275715
0.5714	Remote Similarity	NPC203170
0.5714	Remote Similarity	NPC270041
0.5714	Remote Similarity	NPC326651
0.5714	Remote Similarity	NPC325117
0.5714	Remote Similarity	NPC473741
0.5714	Remote Similarity	NPC474003
0.5714	Remote Similarity	NPC322319
0.5702	Remote Similarity	NPC471120
0.5702	Remote Similarity	NPC471117
0.5699	Remote Similarity	NPC82315
0.5699	Remote Similarity	NPC474812
0.5691	Remote Similarity	NPC310467
0.5686	Remote Similarity	NPC472351
0.5686	Remote Similarity	NPC323180
0.5684	Remote Similarity	NPC315897
0.5682	Remote Similarity	NPC470363
0.568	Remote Similarity	NPC50520
0.5673	Remote Similarity	NPC119633
0.5673	Remote Similarity	NPC270957
0.5673	Remote Similarity	NPC321340
0.5673	Remote Similarity	NPC171698
0.5667	Remote Similarity	NPC472536
0.5667	Remote Similarity	NPC106216
0.5667	Remote Similarity	NPC88898
0.5667	Remote Similarity	NPC103391
0.5664	Remote Similarity	NPC325339
0.5664	Remote Similarity	NPC72401
0.5663	Remote Similarity	NPC322946
0.5657	Remote Similarity	NPC475616
0.5656	Remote Similarity	NPC471121
0.5656	Remote Similarity	NPC471118
0.5652	Remote Similarity	NPC471844
0.5652	Remote Similarity	NPC118524
0.5648	Remote Similarity	NPC469998

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 NPC477729 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	78
0.1-0.2	1878
0.2-0.3	4688
0.3-0.4	1858
0.4-0.5	472
0.5-0.6	147
0.6-0.7	26
0.7-0.8	3
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
0.7816	Intermediate Similarity	NPD7917	Clinical (unspecified phase)
0.7816	Intermediate Similarity	NPD7918	Clinical (unspecified phase)
0.7708	Intermediate Similarity	NPD8394	Approved
0.7113	Intermediate Similarity	NPD3716	Discontinued
0.7097	Intermediate Similarity	NPD7345	Approved
0.6977	Remote Similarity	NPD3724	Clinical (unspecified phase)
0.6932	Remote Similarity	NPD6944	Clinical (unspecified phase)
0.6809	Remote Similarity	NPD1448	Clinical (unspecified phase)
0.6744	Remote Similarity	NPD2263	Discontinued
0.6744	Remote Similarity	NPD1429	Clinical (unspecified phase)
0.6739	Remote Similarity	NPD3160	Suspended
0.6737	Remote Similarity	NPD7643	Phase 1
0.6699	Remote Similarity	NPD6428	Approved
0.6556	Remote Similarity	NPD2256	Clinical (unspecified phase)
0.6548	Remote Similarity	NPD574	Approved
0.6486	Remote Similarity	NPD8306	Approved
0.6486	Remote Similarity	NPD6941	Approved
0.6486	Remote Similarity	NPD8305	Approved
0.6476	Remote Similarity	NPD8038	Phase 2
0.6471	Remote Similarity	NPD575	Clinical (unspecified phase)
0.6374	Remote Similarity	NPD1147	Phase 2
0.6364	Remote Similarity	NPD8393	Approved
0.6364	Remote Similarity	NPD619	Phase 3
0.6337	Remote Similarity	NPD618	Clinical (unspecified phase)
0.633	Remote Similarity	NPD8276	Approved
0.633	Remote Similarity	NPD8045	Clinical (unspecified phase)
0.633	Remote Similarity	NPD8275	Approved
0.6283	Remote Similarity	NPD8087	Discontinued
0.6277	Remote Similarity	NPD2689	Clinical (unspecified phase)
0.6239	Remote Similarity	NPD8084	Approved
0.6239	Remote Similarity	NPD8083	Approved
0.6239	Remote Similarity	NPD8138	Approved
0.6239	Remote Similarity	NPD8086	Approved
0.6239	Remote Similarity	NPD8085	Approved
0.6239	Remote Similarity	NPD8139	Approved
0.6239	Remote Similarity	NPD8082	Approved
0.6196	Remote Similarity	NPD3187	Discontinued
0.6176	Remote Similarity	NPD4264	Clinical (unspecified phase)
0.617	Remote Similarity	NPD1453	Phase 1
0.6162	Remote Similarity	NPD3733	Clinical (unspecified phase)
0.6161	Remote Similarity	NPD8307	Discontinued
0.6161	Remote Similarity	NPD8140	Approved
0.6154	Remote Similarity	NPD6699	Clinical (unspecified phase)
0.614	Remote Similarity	NPD6421	Discontinued
0.6126	Remote Similarity	NPD8081	Approved
0.6121	Remote Similarity	NPD8298	Phase 2
0.6095	Remote Similarity	NPD5781	Clinical (unspecified phase)
0.6068	Remote Similarity	NPD7915	Approved
0.6068	Remote Similarity	NPD7916	Approved
0.6061	Remote Similarity	NPD4829	Discontinued
0.6044	Remote Similarity	NPD4242	Approved
0.604	Remote Similarity	NPD7760	Phase 2
0.604	Remote Similarity	NPD7759	Phase 2
0.6038	Remote Similarity	NPD573	Clinical (unspecified phase)
0.6018	Remote Similarity	NPD8175	Discontinued
0.6	Remote Similarity	NPD9023	Clinical (unspecified phase)
0.6	Remote Similarity	NPD9433	Approved
0.6	Remote Similarity	NPD2257	Approved
0.5981	Remote Similarity	NPD7841	Clinical (unspecified phase)
0.5955	Remote Similarity	NPD7909	Approved
0.595	Remote Similarity	NPD8346	Approved
0.595	Remote Similarity	NPD8347	Approved
0.595	Remote Similarity	NPD8345	Approved
0.5946	Remote Similarity	NPD7140	Approved
0.5946	Remote Similarity	NPD7139	Approved
0.5946	Remote Similarity	NPD7141	Clinical (unspecified phase)
0.5934	Remote Similarity	NPD4241	Registered
0.5922	Remote Similarity	NPD4759	Clinical (unspecified phase)
0.5893	Remote Similarity	NPD6122	Discontinued
0.5882	Remote Similarity	NPD3723	Clinical (unspecified phase)
0.5877	Remote Similarity	NPD1827	Clinical (unspecified phase)
0.5877	Remote Similarity	NPD1829	Clinical (unspecified phase)
0.5877	Remote Similarity	NPD1828	Approved
0.5833	Remote Similarity	NPD7844	Discontinued
0.5826	Remote Similarity	NPD8174	Phase 2
0.5824	Remote Similarity	NPD9421	Phase 1
0.5794	Remote Similarity	NPD1447	Phase 3
0.5794	Remote Similarity	NPD1446	Phase 3
0.578	Remote Similarity	NPD4228	Discovery
0.578	Remote Similarity	NPD3190	Approved
0.578	Remote Similarity	NPD3191	Approved
0.578	Remote Similarity	NPD3189	Approved
0.5776	Remote Similarity	NPD6413	Approved
0.5766	Remote Similarity	NPD8418	Phase 2
0.5755	Remote Similarity	NPD4261	Phase 1
0.5745	Remote Similarity	NPD9446	Approved
0.5745	Remote Similarity	NPD2262	Clinical (unspecified phase)
0.5684	Remote Similarity	NPD1825	Clinical (unspecified phase)
0.5676	Remote Similarity	NPD2255	Approved
0.5664	Remote Similarity	NPD8300	Approved
0.5664	Remote Similarity	NPD8301	Approved
0.5663	Remote Similarity	NPD9441	Phase 2
0.5652	Remote Similarity	NPD886	Clinical (unspecified phase)
0.5638	Remote Similarity	NPD2696	Approved
0.5638	Remote Similarity	NPD2694	Approved
0.5638	Remote Similarity	NPD2697	Approved
0.5638	Remote Similarity	NPD2695	Approved
0.5604	Remote Similarity	NPD1831	Phase 3
0.5604	Remote Similarity	NPD348	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