NPASS Compound

Structure

NPC51391 OpenBabel07101718242D 26 26 0 0 1 0 0 0 0 0999 V2000 -0.3704 6.8772 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3015 -3.0167 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3040 6.5188 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4604 5.5311 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6833 4.9018 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8397 3.9141 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6800 0.7420 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6745 0.6375 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0626 3.2848 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2733 1.6555 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0813 -0.2761 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2190 2.2971 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2788 1.7601 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0758 -0.3806 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1526 1.9387 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6180 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3090 0.9511 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8090 -0.5878 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4825 -1.2941 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3090 0.9511 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8090 -1.5878 0.0000 I 0 0 0 0 0 0 0 0 0 0 0 0 5.4771 -1.3987 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.9511 -0.3090 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.3081 0.9079 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.8948 -2.1032 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 3 1 0 0 0 0 2 26 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 9 1 0 0 0 0 7 8 1 0 0 0 0 7 10 2 0 0 0 0 8 11 1 0 0 0 0 9 12 2 0 0 0 0 10 13 1 0 0 0 0 11 14 1 0 0 0 0 12 15 1 0 0 0 0 13 17 2 0 0 0 0 14 19 1 0 0 0 0 15 21 1 0 0 0 0 16 18 2 0 0 0 0 16 21 1 0 0 0 0 17 20 1 0 0 0 0 17 21 1 0 0 0 0 18 20 1 0 0 0 0 18 22 1 0 0 0 0 19 23 2 0 0 0 0 19 26 1 0 0 0 0 20 24 2 0 0 0 0 21 25 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	304.09
Volume:	296.545
LogP:	1.68
LogD:	1.445
LogS:	-3.314
# Rotatable Bonds:	4
TPSA:	93.04
# H-Bond Aceptor:	6
# H-Bond Donor:	2
# Rings:	3
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.717
Synthetic Accessibility Score:	3.335
Fsp3:	0.312
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.967
MDCK Permeability:	2.4556220523663796e-05
Pgp-inhibitor:	0.005
Pgp-substrate:	0.105
Human Intestinal Absorption (HIA):	0.018
20% Bioavailability (F20%):	0.025
30% Bioavailability (F30%):	0.094

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.031
Plasma Protein Binding (PPB):	82.63475799560547%
Volume Distribution (VD):	0.868
Pgp-substrate:	12.484064102172852%

ADMET: Metabolism

CYP1A2-inhibitor:	0.922
CYP1A2-substrate:	0.328
CYP2C19-inhibitor:	0.163
CYP2C19-substrate:	0.067
CYP2C9-inhibitor:	0.462
CYP2C9-substrate:	0.294
CYP2D6-inhibitor:	0.683
CYP2D6-substrate:	0.346
CYP3A4-inhibitor:	0.258
CYP3A4-substrate:	0.189

ADMET: Excretion

Clearance (CL):	10.868
Half-life (T1/2):	0.679

ADMET: Toxicity

hERG Blockers:	0.029
Human Hepatotoxicity (H-HT):	0.444
Drug-inuced Liver Injury (DILI):	0.948
AMES Toxicity:	0.16
Rat Oral Acute Toxicity:	0.301
Maximum Recommended Daily Dose:	0.836
Skin Sensitization:	0.166
Carcinogencity:	0.838
Eye Corrosion:	0.003
Eye Irritation:	0.018
Respiratory Toxicity:	0.179

Download Data

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

Natural Product: NPC51391

Natural Product ID:	NPC51391
*Common Name:**	Iodovulone Iii
IUPAC Name:	methyl (E,7Z)-7-[(2R)-2-hydroxy-4-iodo-2-[(Z)-oct-2-enyl]-5-oxocyclopent-3-en-1-ylidene]hept-5-enoate
Synonyms:	Iodovulone Iii
Standard InCHIKey:	WBVIHDHLOOPYQN-MNSXJSHLSA-N
Standard InCHI:	InChI=1S/C21H29IO4/c1-3-4-5-6-9-12-15-21(25)16-18(22)20(24)17(21)13-10-7-8-11-14-19(23)26-2/h7,9-10,12-13,16,25H,3-6,8,11,14-15H2,1-2H3/b10-7+,12-9-,17-13+/t21-/m1/s1
SMILES:	CCCCC/C=CC[C@@]1(O)C=C(C(=O)/C/1=CC=CCCCC(=O)OC)I
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL465973
PubChem CID:	11225221
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0003909] Fatty Acyls [CHEMONTID:0000513] Eicosanoids [CHEMONTID:0001021] Clavulones and derivatives

*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
NPO3077	Clavularia viridis	Species	Clavulariidae	Eukaryota	n.a.	Okinawan	n.a.	PMID[11720524]
NPO3077	Clavularia viridis	Species	Clavulariidae	Eukaryota	n.a.	Formosan soft corals	n.a.	PMID[12444673]
NPO3077	Clavularia viridis	Species	Clavulariidae	Eukaryota	n.a.	Taiwanese octocoral	n.a.	PMID[15104481]
NPO3077	Clavularia viridis	Species	Clavulariidae	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	2

Activity Type	# Activity
Cell Line	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT306	Cell Line	PC-3	Homo sapiens	IC50	=	6700.0	nM	PMID[526681]
NPT139	Cell Line	HT-29	Homo sapiens	IC50	>	10000.0	nM	PMID[526681]

☑ 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 NPC51391 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	168
0.1-0.2	1304
0.2-0.3	7855
0.3-0.4	18120
0.4-0.5	9944
0.5-0.6	4265
0.6-0.7	979
0.7-0.8	53
0.8-0.85	0
0.85-0.9	4
0.9-0.95	0
0.95-1	5

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC4492
0.9571	High Similarity	NPC238948
0.9571	High Similarity	NPC215745
0.9571	High Similarity	NPC12815
0.8816	High Similarity	NPC265980
0.8816	High Similarity	NPC63326
0.8514	High Similarity	NPC287878
0.8481	Intermediate Similarity	NPC26624
0.8028	Intermediate Similarity	NPC322457
0.7662	Intermediate Similarity	NPC319163
0.7662	Intermediate Similarity	NPC67076
0.7632	Intermediate Similarity	NPC476059
0.7632	Intermediate Similarity	NPC473603
0.7632	Intermediate Similarity	NPC236208
0.7532	Intermediate Similarity	NPC318766
0.75	Intermediate Similarity	NPC16488
0.747	Intermediate Similarity	NPC474980
0.7468	Intermediate Similarity	NPC122244
0.7442	Intermediate Similarity	NPC316426
0.7442	Intermediate Similarity	NPC315395
0.7436	Intermediate Similarity	NPC106309
0.7397	Intermediate Similarity	NPC64985
0.7375	Intermediate Similarity	NPC260396
0.7356	Intermediate Similarity	NPC72513
0.7349	Intermediate Similarity	NPC160582
0.7326	Intermediate Similarity	NPC125290
0.7317	Intermediate Similarity	NPC279532
0.7297	Intermediate Similarity	NPC190049
0.725	Intermediate Similarity	NPC227396
0.7215	Intermediate Similarity	NPC316185
0.7179	Intermediate Similarity	NPC470693
0.7176	Intermediate Similarity	NPC85772
0.716	Intermediate Similarity	NPC225665
0.716	Intermediate Similarity	NPC166018
0.716	Intermediate Similarity	NPC169056
0.716	Intermediate Similarity	NPC68624
0.7143	Intermediate Similarity	NPC21998
0.7143	Intermediate Similarity	NPC474127
0.7143	Intermediate Similarity	NPC322461
0.7126	Intermediate Similarity	NPC261380
0.7123	Intermediate Similarity	NPC86789
0.7108	Intermediate Similarity	NPC192006
0.7108	Intermediate Similarity	NPC476627
0.7108	Intermediate Similarity	NPC93763
0.7108	Intermediate Similarity	NPC267231
0.7108	Intermediate Similarity	NPC108816
0.7105	Intermediate Similarity	NPC470688
0.7093	Intermediate Similarity	NPC161045
0.7079	Intermediate Similarity	NPC26078
0.7079	Intermediate Similarity	NPC473658
0.7073	Intermediate Similarity	NPC203277
0.7067	Intermediate Similarity	NPC68110
0.7059	Intermediate Similarity	NPC325031
0.7045	Intermediate Similarity	NPC234038
0.7037	Intermediate Similarity	NPC470686
0.7037	Intermediate Similarity	NPC114727
0.7037	Intermediate Similarity	NPC315843
0.7037	Intermediate Similarity	NPC476590
0.7033	Intermediate Similarity	NPC180617
0.7033	Intermediate Similarity	NPC111114
0.7033	Intermediate Similarity	NPC32552
0.7033	Intermediate Similarity	NPC261607
0.7033	Intermediate Similarity	NPC142838
0.7033	Intermediate Similarity	NPC300312
0.7024	Intermediate Similarity	NPC472013
0.7024	Intermediate Similarity	NPC476624
0.7013	Intermediate Similarity	NPC142423
0.7013	Intermediate Similarity	NPC308294
0.7011	Intermediate Similarity	NPC219966
0.7	Intermediate Similarity	NPC293114
0.7	Intermediate Similarity	NPC288667
0.7	Intermediate Similarity	NPC307092
0.7	Intermediate Similarity	NPC126061
0.7	Intermediate Similarity	NPC51358
0.6962	Remote Similarity	NPC67608
0.6962	Remote Similarity	NPC473277
0.6962	Remote Similarity	NPC143396
0.6957	Remote Similarity	NPC29798
0.6957	Remote Similarity	NPC282644
0.6951	Remote Similarity	NPC329852
0.6951	Remote Similarity	NPC161038
0.6944	Remote Similarity	NPC325977
0.6933	Remote Similarity	NPC263732
0.6932	Remote Similarity	NPC11804
0.6932	Remote Similarity	NPC470755
0.6923	Remote Similarity	NPC106613
0.6923	Remote Similarity	NPC475879
0.6914	Remote Similarity	NPC153660
0.6905	Remote Similarity	NPC182292
0.6905	Remote Similarity	NPC264391
0.6905	Remote Similarity	NPC248624
0.6892	Remote Similarity	NPC329249
0.6892	Remote Similarity	NPC318306
0.6889	Remote Similarity	NPC153570
0.6889	Remote Similarity	NPC260343
0.6883	Remote Similarity	NPC220766
0.6882	Remote Similarity	NPC167219
0.6875	Remote Similarity	NPC203819
0.6875	Remote Similarity	NPC67183
0.6867	Remote Similarity	NPC256640
0.6867	Remote Similarity	NPC205615
0.6867	Remote Similarity	NPC16279
0.6854	Remote Similarity	NPC261721
0.6854	Remote Similarity	NPC291712
0.6849	Remote Similarity	NPC283502
0.6848	Remote Similarity	NPC472705
0.6842	Remote Similarity	NPC245521
0.6842	Remote Similarity	NPC155849
0.6835	Remote Similarity	NPC470256
0.6835	Remote Similarity	NPC309466
0.6835	Remote Similarity	NPC476614
0.6829	Remote Similarity	NPC107654
0.6824	Remote Similarity	NPC99651
0.6824	Remote Similarity	NPC164308
0.6818	Remote Similarity	NPC158756
0.6818	Remote Similarity	NPC196487
0.6818	Remote Similarity	NPC14575
0.6813	Remote Similarity	NPC118011
0.6813	Remote Similarity	NPC212598
0.6813	Remote Similarity	NPC36668
0.6813	Remote Similarity	NPC87306
0.6809	Remote Similarity	NPC209355
0.6804	Remote Similarity	NPC469851
0.6795	Remote Similarity	NPC146811
0.6795	Remote Similarity	NPC191233
0.6786	Remote Similarity	NPC82666
0.6786	Remote Similarity	NPC7563
0.6786	Remote Similarity	NPC472014
0.6786	Remote Similarity	NPC97173
0.6786	Remote Similarity	NPC275530
0.6786	Remote Similarity	NPC320630
0.6786	Remote Similarity	NPC116177
0.6778	Remote Similarity	NPC160138
0.6778	Remote Similarity	NPC471738
0.6778	Remote Similarity	NPC473248
0.6757	Remote Similarity	NPC471619
0.675	Remote Similarity	NPC88877
0.675	Remote Similarity	NPC476591
0.675	Remote Similarity	NPC151481
0.675	Remote Similarity	NPC475982
0.6747	Remote Similarity	NPC478191
0.6747	Remote Similarity	NPC478195
0.6747	Remote Similarity	NPC478193
0.6747	Remote Similarity	NPC478192
0.6747	Remote Similarity	NPC478196
0.6747	Remote Similarity	NPC478194
0.6744	Remote Similarity	NPC115418
0.6742	Remote Similarity	NPC476628
0.6742	Remote Similarity	NPC281172
0.6742	Remote Similarity	NPC307112
0.6739	Remote Similarity	NPC77337
0.6739	Remote Similarity	NPC179394
0.6739	Remote Similarity	NPC144133
0.6739	Remote Similarity	NPC473455
0.6714	Remote Similarity	NPC43053
0.6712	Remote Similarity	NPC472808
0.6712	Remote Similarity	NPC324224
0.6711	Remote Similarity	NPC40082
0.6711	Remote Similarity	NPC151648
0.6709	Remote Similarity	NPC203335
0.6709	Remote Similarity	NPC194871
0.6707	Remote Similarity	NPC284006
0.6706	Remote Similarity	NPC478122
0.6706	Remote Similarity	NPC253749
0.6706	Remote Similarity	NPC315765
0.6706	Remote Similarity	NPC169095
0.6705	Remote Similarity	NPC475083
0.6705	Remote Similarity	NPC250315
0.6705	Remote Similarity	NPC40746
0.6705	Remote Similarity	NPC169575
0.6703	Remote Similarity	NPC72397
0.6703	Remote Similarity	NPC475819
0.6703	Remote Similarity	NPC476805
0.6667	Remote Similarity	NPC122502
0.6667	Remote Similarity	NPC469910
0.6667	Remote Similarity	NPC472017
0.6667	Remote Similarity	NPC112868
0.6667	Remote Similarity	NPC42470
0.6667	Remote Similarity	NPC275766
0.6667	Remote Similarity	NPC59994
0.6667	Remote Similarity	NPC329550
0.6667	Remote Similarity	NPC275507
0.6667	Remote Similarity	NPC473986
0.6667	Remote Similarity	NPC68819
0.6667	Remote Similarity	NPC78677
0.6667	Remote Similarity	NPC59558
0.6667	Remote Similarity	NPC471566
0.6667	Remote Similarity	NPC474018
0.6667	Remote Similarity	NPC315597
0.6667	Remote Similarity	NPC472009
0.6667	Remote Similarity	NPC32944
0.6667	Remote Similarity	NPC471556
0.6667	Remote Similarity	NPC193396
0.6667	Remote Similarity	NPC471565
0.6667	Remote Similarity	NPC315285
0.6633	Remote Similarity	NPC206079
0.6632	Remote Similarity	NPC214694
0.663	Remote Similarity	NPC106040
0.663	Remote Similarity	NPC115179
0.6629	Remote Similarity	NPC31086

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 NPC51391 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	143
0.1-0.2	1810
0.2-0.3	4290
0.3-0.4	2175
0.4-0.5	600
0.5-0.6	102
0.6-0.7	30
0.7-0.8	0
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
0.7176	Intermediate Similarity	NPD5209	Approved
0.6988	Remote Similarity	NPD4756	Discovery
0.6932	Remote Similarity	NPD5363	Approved
0.6744	Remote Similarity	NPD4252	Approved
0.6739	Remote Similarity	NPD5785	Approved
0.6591	Remote Similarity	NPD4270	Approved
0.6591	Remote Similarity	NPD4269	Approved
0.6579	Remote Similarity	NPD4246	Clinical (unspecified phase)
0.6517	Remote Similarity	NPD7154	Phase 3
0.6517	Remote Similarity	NPD5362	Discontinued
0.65	Remote Similarity	NPD4247	Clinical (unspecified phase)
0.6484	Remote Similarity	NPD5786	Approved
0.6477	Remote Similarity	NPD5369	Approved
0.6429	Remote Similarity	NPD4220	Pre-registration
0.6364	Remote Similarity	NPD4822	Approved
0.6364	Remote Similarity	NPD4821	Approved
0.6364	Remote Similarity	NPD4820	Approved
0.6364	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD4819	Approved
0.6322	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6322	Remote Similarity	NPD4271	Approved
0.6322	Remote Similarity	NPD4268	Approved
0.6316	Remote Similarity	NPD7983	Approved
0.6316	Remote Similarity	NPD7637	Suspended
0.6289	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6282	Remote Similarity	NPD4193	Approved
0.6282	Remote Similarity	NPD4194	Approved
0.6282	Remote Similarity	NPD4191	Approved
0.6282	Remote Similarity	NPD4192	Approved
0.6277	Remote Similarity	NPD5370	Suspended
0.625	Remote Similarity	NPD5779	Approved
0.625	Remote Similarity	NPD5778	Approved
0.6196	Remote Similarity	NPD1696	Phase 3
0.6176	Remote Similarity	NPD6647	Phase 2
0.6154	Remote Similarity	NPD5332	Approved
0.6154	Remote Similarity	NPD5331	Approved
0.6146	Remote Similarity	NPD4810	Clinical (unspecified phase)
0.6111	Remote Similarity	NPD4790	Discontinued
0.61	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6061	Remote Similarity	NPD7839	Suspended
0.6049	Remote Similarity	NPD2685	Clinical (unspecified phase)
0.6042	Remote Similarity	NPD7838	Discovery
0.6	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.6	Remote Similarity	NPD4222	Approved
0.5981	Remote Similarity	NPD6371	Approved
0.5976	Remote Similarity	NPD7331	Phase 2
0.5972	Remote Similarity	NPD3173	Approved
0.5957	Remote Similarity	NPD4249	Approved
0.5941	Remote Similarity	NPD4225	Approved
0.5938	Remote Similarity	NPD6101	Approved
0.5938	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.5914	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.5895	Remote Similarity	NPD4250	Approved
0.5895	Remote Similarity	NPD4251	Approved
0.5859	Remote Similarity	NPD5282	Discontinued
0.5849	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.5816	Remote Similarity	NPD5281	Approved
0.5816	Remote Similarity	NPD6411	Approved
0.5816	Remote Similarity	NPD5284	Approved
0.5806	Remote Similarity	NPD6110	Phase 1
0.5802	Remote Similarity	NPD2664	Clinical (unspecified phase)
0.5795	Remote Similarity	NPD8039	Approved
0.5789	Remote Similarity	NPD4623	Approved
0.5789	Remote Similarity	NPD4519	Discontinued
0.578	Remote Similarity	NPD7601	Clinical (unspecified phase)
0.5775	Remote Similarity	NPD39	Approved
0.5714	Remote Similarity	NPD9411	Phase 1
0.5714	Remote Similarity	NPD6698	Approved
0.5714	Remote Similarity	NPD46	Approved
0.5699	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.5699	Remote Similarity	NPD4800	Clinical (unspecified phase)
0.5699	Remote Similarity	NPD6435	Approved
0.5664	Remote Similarity	NPD7115	Discovery
0.5658	Remote Similarity	NPD3172	Approved
0.5652	Remote Similarity	NPD5368	Approved
0.5616	Remote Similarity	NPD5343	Approved
0.5604	Remote Similarity	NPD7322	Clinical (unspecified phase)
0.56	Remote Similarity	NPD6927	Phase 3

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