NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	872.44
Volume:	885.243
LogP:	2.256
LogD:	2.391
LogS:	-4.808
# Rotatable Bonds:	33
TPSA:	250.12
# H-Bond Aceptor:	18
# H-Bond Donor:	3
# Rings:	2
# Heavy Atoms:	18

MedChem Properties

QED Drug-Likeness Score:	0.043
Synthetic Accessibility Score:	6.224
Fsp3:	0.591
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.905
MDCK Permeability:	1.509320645709522e-05
Pgp-inhibitor:	0.997
Pgp-substrate:	0.995
Human Intestinal Absorption (HIA):	0.529
20% Bioavailability (F20%):	0.009
30% Bioavailability (F30%):	0.999

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.235
Plasma Protein Binding (PPB):	90.5140151977539%
Volume Distribution (VD):	3.119
Pgp-substrate:	4.1215996742248535%

ADMET: Metabolism

CYP1A2-inhibitor:	0.002
CYP1A2-substrate:	0.099
CYP2C19-inhibitor:	0.007
CYP2C19-substrate:	0.051
CYP2C9-inhibitor:	0.011
CYP2C9-substrate:	0.038
CYP2D6-inhibitor:	0.002
CYP2D6-substrate:	0.108
CYP3A4-inhibitor:	0.57
CYP3A4-substrate:	0.264

ADMET: Excretion

Clearance (CL):	10.545
Half-life (T1/2):	0.158

ADMET: Toxicity

hERG Blockers:	0.007
Human Hepatotoxicity (H-HT):	0.517
Drug-inuced Liver Injury (DILI):	0.928
AMES Toxicity:	0.005
Rat Oral Acute Toxicity:	0.962
Maximum Recommended Daily Dose:	0.94
Skin Sensitization:	0.018
Carcinogencity:	0.932
Eye Corrosion:	0.003
Eye Irritation:	0.004
Respiratory Toxicity:	0.036

Download Data

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

Natural Product: NPC476832

Natural Product ID:	NPC476832
*Common Name:**	Secohalichondramide
IUPAC Name:	methyl 4-[4-[(E)-9-[(2E,17E)-1-amino-18-[formyl(methyl)amino]-9,15-dimethoxy-6,10,14-trimethyl-1,13-dioxooctadeca-2,17-dien-7-yl]oxy-7-hydroxy-1-methoxy-2-methyl-3,9-dioxonon-4-enyl]-1,3-oxazol-2-yl]-1,3-oxazole-2-carboxylate
Synonyms:	Secohalichondramide
Standard InCHIKey:	NWHQAZYYZFUYMW-JKQLDQSBSA-N
Standard InCHI:	InChI=1S/C44H64N4O14/c1-27(14-10-11-18-39(45)53)38(23-37(57-7)28(2)19-20-35(52)29(3)36(56-6)17-13-21-48(5)26-49)62-40(54)22-31(50)15-12-16-34(51)30(4)41(58-8)32-24-60-42(46-32)33-25-61-43(47-33)44(55)59-9/h11-13,16,18,21,24-31,36-38,41,50H,10,14-15,17,19-20,22-23H2,1-9H3,(H2,45,53)/b16-12+,18-11+,21-13+
SMILES:	CC(CC/C=C/C(=O)N)C(CC(C(C)CCC(=O)C(C)C(C/C=C/N(C)C=O)OC)OC)OC(=O)CC(C/C=C/C(=O)C(C)C(C1=COC(=N1)C2=COC(=N2)C(=O)OC)OC)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	n.a.
PubChem CID:	11787796
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001551] Diterpenoids

*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
NPO17255	Chondrosia corticata	Species	Chondrillidae	Eukaryota	n.a.	n.a.	n.a.	PMID[15568783]
NPO17255	Chondrosia corticata	Species	Chondrillidae	Eukaryota	n.a.	reef slopes on the south side of Cocos Lagoon, Guam	n.a.	PMID[21550239]
NPO17255	Chondrosia corticata	Species	Chondrillidae	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
Others	2

Activity Type	# Activity
Cell Line	1
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT111	Cell Line	K562	Homo sapiens	LC50	>	500	ug/ml	PMID[15568783]
NPT20	Organism	Candida albicans	Candida albicans	IZ	=	15	mm	PMID[15568783]

☑ 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 NPC476832 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	253
0.1-0.2	1619
0.2-0.3	9202
0.3-0.4	20881
0.4-0.5	9577
0.5-0.6	1075
0.6-0.7	43
0.7-0.8	16
0.8-0.85	0
0.85-0.9	14
0.9-0.95	15
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9417	High Similarity	NPC476830
0.9369	High Similarity	NPC476826
0.9369	High Similarity	NPC476827
0.9369	High Similarity	NPC476831
0.9234	High Similarity	NPC476828
0.9061	High Similarity	NPC477218
0.9048	High Similarity	NPC477219
0.9014	High Similarity	NPC299035
0.9014	High Similarity	NPC177432
0.9005	High Similarity	NPC37924
0.8972	High Similarity	NPC322800
0.8972	High Similarity	NPC168135
0.8962	High Similarity	NPC325683
0.8806	High Similarity	NPC476829
0.7376	Intermediate Similarity	NPC258022
0.7204	Intermediate Similarity	NPC58001
0.7204	Intermediate Similarity	NPC314523
0.7167	Intermediate Similarity	NPC477586
0.7167	Intermediate Similarity	NPC477588
0.7167	Intermediate Similarity	NPC477585
0.7167	Intermediate Similarity	NPC477590
0.7149	Intermediate Similarity	NPC48323
0.7149	Intermediate Similarity	NPC289029
0.7104	Intermediate Similarity	NPC208297
0.7104	Intermediate Similarity	NPC224395
0.7083	Intermediate Similarity	NPC477589
0.7083	Intermediate Similarity	NPC477587
0.7059	Intermediate Similarity	NPC295653
0.7059	Intermediate Similarity	NPC107458
0.6971	Remote Similarity	NPC30527
0.6878	Remote Similarity	NPC306300
0.6878	Remote Similarity	NPC58112
0.6878	Remote Similarity	NPC88938
0.6833	Remote Similarity	NPC199461
0.6833	Remote Similarity	NPC103452
0.6833	Remote Similarity	NPC46313
0.6624	Remote Similarity	NPC309919
0.6601	Remote Similarity	NPC165964
0.6568	Remote Similarity	NPC315411
0.6486	Remote Similarity	NPC472436
0.6485	Remote Similarity	NPC49195
0.6448	Remote Similarity	NPC258048
0.6437	Remote Similarity	NPC102593
0.6437	Remote Similarity	NPC196718
0.6421	Remote Similarity	NPC196449
0.6421	Remote Similarity	NPC314222
0.6415	Remote Similarity	NPC211555
0.64	Remote Similarity	NPC315061
0.6371	Remote Similarity	NPC472435
0.6368	Remote Similarity	NPC186452
0.6339	Remote Similarity	NPC316224
0.625	Remote Similarity	NPC12660
0.6239	Remote Similarity	NPC315872
0.6221	Remote Similarity	NPC54983
0.622	Remote Similarity	NPC314633
0.6214	Remote Similarity	NPC314270
0.6212	Remote Similarity	NPC473833
0.6139	Remote Similarity	NPC161801
0.6122	Remote Similarity	NPC313804
0.6122	Remote Similarity	NPC315804
0.6122	Remote Similarity	NPC475301
0.6122	Remote Similarity	NPC326930
0.6105	Remote Similarity	NPC471978
0.61	Remote Similarity	NPC72715
0.6091	Remote Similarity	NPC477979
0.6078	Remote Similarity	NPC184680
0.6062	Remote Similarity	NPC472434
0.6061	Remote Similarity	NPC53255
0.6061	Remote Similarity	NPC85879
0.6055	Remote Similarity	NPC470784
0.6055	Remote Similarity	NPC470785
0.6049	Remote Similarity	NPC207620
0.6045	Remote Similarity	NPC328928
0.6038	Remote Similarity	NPC13603
0.6028	Remote Similarity	NPC169716
0.6024	Remote Similarity	NPC323752
0.6023	Remote Similarity	NPC471015
0.6008	Remote Similarity	NPC148889
0.6	Remote Similarity	NPC316403
0.6	Remote Similarity	NPC182222
0.5992	Remote Similarity	NPC194740
0.5992	Remote Similarity	NPC474183
0.5978	Remote Similarity	NPC471979
0.5968	Remote Similarity	NPC128115
0.5963	Remote Similarity	NPC152620
0.5961	Remote Similarity	NPC323198
0.596	Remote Similarity	NPC205372
0.5954	Remote Similarity	NPC324619
0.5954	Remote Similarity	NPC475315
0.5952	Remote Similarity	NPC186351
0.5952	Remote Similarity	NPC244536
0.5916	Remote Similarity	NPC58209
0.5916	Remote Similarity	NPC475533
0.5911	Remote Similarity	NPC312645
0.59	Remote Similarity	NPC291609
0.5892	Remote Similarity	NPC472287
0.5892	Remote Similarity	NPC472286
0.5891	Remote Similarity	NPC240384
0.5887	Remote Similarity	NPC181081
0.5887	Remote Similarity	NPC131885
0.5871	Remote Similarity	NPC91868
0.5871	Remote Similarity	NPC63971
0.5862	Remote Similarity	NPC124300
0.5861	Remote Similarity	NPC269367
0.5857	Remote Similarity	NPC478141
0.5856	Remote Similarity	NPC310618
0.5855	Remote Similarity	NPC473639
0.5841	Remote Similarity	NPC475455
0.584	Remote Similarity	NPC323969
0.5837	Remote Similarity	NPC141053
0.5837	Remote Similarity	NPC284888
0.5833	Remote Similarity	NPC143977
0.583	Remote Similarity	NPC215837
0.5827	Remote Similarity	NPC315893
0.5827	Remote Similarity	NPC313587
0.5827	Remote Similarity	NPC316110
0.582	Remote Similarity	NPC260434
0.582	Remote Similarity	NPC14288
0.5817	Remote Similarity	NPC471013
0.5817	Remote Similarity	NPC180668
0.5817	Remote Similarity	NPC148896
0.581	Remote Similarity	NPC289423
0.581	Remote Similarity	NPC212766
0.581	Remote Similarity	NPC97746
0.5809	Remote Similarity	NPC209981
0.5809	Remote Similarity	NPC317572
0.5806	Remote Similarity	NPC85702
0.5803	Remote Similarity	NPC470042
0.5799	Remote Similarity	NPC53534
0.5798	Remote Similarity	NPC89987
0.5792	Remote Similarity	NPC57453
0.5789	Remote Similarity	NPC89508
0.5787	Remote Similarity	NPC319232
0.5787	Remote Similarity	NPC24370
0.5784	Remote Similarity	NPC314882
0.5781	Remote Similarity	NPC322135
0.5779	Remote Similarity	NPC160100
0.5779	Remote Similarity	NPC75179
0.5778	Remote Similarity	NPC476514
0.5775	Remote Similarity	NPC220852
0.5766	Remote Similarity	NPC153452
0.5766	Remote Similarity	NPC16066
0.5765	Remote Similarity	NPC140296
0.576	Remote Similarity	NPC303658
0.5753	Remote Similarity	NPC475619
0.5751	Remote Similarity	NPC230683
0.5747	Remote Similarity	NPC101350
0.5745	Remote Similarity	NPC227824
0.5742	Remote Similarity	NPC100547
0.5741	Remote Similarity	NPC166712
0.5737	Remote Similarity	NPC288987
0.5732	Remote Similarity	NPC123839
0.573	Remote Similarity	NPC10904
0.5726	Remote Similarity	NPC74562
0.5726	Remote Similarity	NPC316181
0.5726	Remote Similarity	NPC151781
0.572	Remote Similarity	NPC223409
0.572	Remote Similarity	NPC95240
0.572	Remote Similarity	NPC472259
0.572	Remote Similarity	NPC208364
0.572	Remote Similarity	NPC188400
0.5714	Remote Similarity	NPC470903
0.5714	Remote Similarity	NPC167763
0.5714	Remote Similarity	NPC470112
0.5709	Remote Similarity	NPC14812
0.5709	Remote Similarity	NPC67401
0.5709	Remote Similarity	NPC285343
0.5709	Remote Similarity	NPC473800
0.5709	Remote Similarity	NPC235685
0.5708	Remote Similarity	NPC220408
0.5708	Remote Similarity	NPC18487
0.5703	Remote Similarity	NPC261251
0.5703	Remote Similarity	NPC66191
0.5703	Remote Similarity	NPC34580
0.5703	Remote Similarity	NPC304307
0.5703	Remote Similarity	NPC316297
0.5703	Remote Similarity	NPC118559
0.5703	Remote Similarity	NPC314817
0.5703	Remote Similarity	NPC124920
0.5699	Remote Similarity	NPC478006
0.5692	Remote Similarity	NPC90019
0.5692	Remote Similarity	NPC34770
0.5691	Remote Similarity	NPC478158
0.5686	Remote Similarity	NPC122886
0.5685	Remote Similarity	NPC121327
0.5685	Remote Similarity	NPC473493
0.5678	Remote Similarity	NPC185197
0.5678	Remote Similarity	NPC129909
0.5676	Remote Similarity	NPC54803
0.5676	Remote Similarity	NPC321592
0.5675	Remote Similarity	NPC298436
0.5672	Remote Similarity	NPC203373
0.5672	Remote Similarity	NPC26543
0.5669	Remote Similarity	NPC260909
0.5667	Remote Similarity	NPC244543
0.5664	Remote Similarity	NPC214142
0.5657	Remote Similarity	NPC472285
0.5654	Remote Similarity	NPC329631
0.5652	Remote Similarity	NPC54066
0.565	Remote Similarity	NPC266249

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 NPC476832 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	154
0.1-0.2	514
0.2-0.3	1644
0.3-0.4	3587
0.4-0.5	2871
0.5-0.6	362
0.6-0.7	17
0.7-0.8	1
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
0.6875	Remote Similarity	NPD7896	Approved
0.6571	Remote Similarity	NPD7031	Phase 1
0.6498	Remote Similarity	NPD4667	Clinical (unspecified phase)
0.6492	Remote Similarity	NPD7853	Phase 2
0.6352	Remote Similarity	NPD7547	Clinical (unspecified phase)
0.6332	Remote Similarity	NPD6347	Phase 2
0.6331	Remote Similarity	NPD7284	Clinical (unspecified phase)
0.631	Remote Similarity	NPD4394	Clinical (unspecified phase)
0.6306	Remote Similarity	NPD5922	Phase 3
0.628	Remote Similarity	NPD4373	Phase 2
0.6269	Remote Similarity	NPD8370	Discontinued
0.6239	Remote Similarity	NPD6444	Clinical (unspecified phase)
0.6234	Remote Similarity	NPD7490	Discontinued
0.6225	Remote Similarity	NPD4952	Phase 3
0.6225	Remote Similarity	NPD7589	Clinical (unspecified phase)
0.6225	Remote Similarity	NPD4898	Clinical (unspecified phase)
0.6224	Remote Similarity	NPD1638	Discovery
0.6189	Remote Similarity	NPD6974	Phase 3
0.6172	Remote Similarity	NPD7022	Phase 2
0.6163	Remote Similarity	NPD7180	Phase 3
0.6142	Remote Similarity	NPD4368	Phase 2
0.6132	Remote Similarity	NPD2433	Clinical (unspecified phase)
0.6126	Remote Similarity	NPD2951	Discontinued
0.6107	Remote Similarity	NPD5443	Clinical (unspecified phase)
0.6104	Remote Similarity	NPD5640	Discontinued
0.6102	Remote Similarity	NPD2779	Approved
0.6084	Remote Similarity	NPD5532	Phase 2
0.6067	Remote Similarity	NPD4392	Phase 2
0.6064	Remote Similarity	NPD6247	Clinical (unspecified phase)
0.6049	Remote Similarity	NPD3945	Discontinued
0.6032	Remote Similarity	NPD8479	Phase 2
0.6025	Remote Similarity	NPD5293	Phase 2
0.6023	Remote Similarity	NPD6495	Clinical (unspecified phase)
0.6016	Remote Similarity	NPD4958	Clinical (unspecified phase)
0.6015	Remote Similarity	NPD7393	Clinical (unspecified phase)
0.6008	Remote Similarity	NPD5866	Approved
0.6	Remote Similarity	NPD8329	Phase 3
0.5993	Remote Similarity	NPD3801	Clinical (unspecified phase)
0.5993	Remote Similarity	NPD7690	Clinical (unspecified phase)
0.5992	Remote Similarity	NPD4900	Clinical (unspecified phase)
0.5985	Remote Similarity	NPD8117	Approved
0.5985	Remote Similarity	NPD8116	Phase 3
0.5984	Remote Similarity	NPD8356	Approved
0.5975	Remote Similarity	NPD2778	Approved
0.5968	Remote Similarity	NPD1659	Phase 1
0.5952	Remote Similarity	NPD7268	Clinical (unspecified phase)
0.5952	Remote Similarity	NPD8430	Approved
0.5952	Remote Similarity	NPD4086	Phase 1
0.5945	Remote Similarity	NPD6962	Phase 2
0.5932	Remote Similarity	NPD8324	Phase 2
0.5932	Remote Similarity	NPD8279	Clinical (unspecified phase)
0.5926	Remote Similarity	NPD3392	Approved
0.5925	Remote Similarity	NPD5857	Phase 3
0.5923	Remote Similarity	NPD6716	Phase 1
0.5922	Remote Similarity	NPD7796	Approved
0.5922	Remote Similarity	NPD7797	Approved
0.592	Remote Similarity	NPD6824	Clinical (unspecified phase)
0.5913	Remote Similarity	NPD3263	Phase 3
0.5907	Remote Similarity	NPD6857	Phase 3
0.5907	Remote Similarity	NPD2921	Clinical (unspecified phase)
0.5907	Remote Similarity	NPD5908	Clinical (unspecified phase)
0.5902	Remote Similarity	NPD8463	Approved
0.5902	Remote Similarity	NPD6567	Clinical (unspecified phase)
0.5894	Remote Similarity	NPD6169	Phase 1
0.5892	Remote Similarity	NPD3507	Phase 2
0.588	Remote Similarity	NPD8247	Approved
0.588	Remote Similarity	NPD8246	Approved
0.5873	Remote Similarity	NPD3925	Approved
0.5853	Remote Similarity	NPD3006	Discontinued
0.5843	Remote Similarity	NPD8374	Phase 3
0.5843	Remote Similarity	NPD5924	Discontinued
0.5827	Remote Similarity	NPD7994	Phase 2
0.5826	Remote Similarity	NPD4901	Clinical (unspecified phase)
0.5823	Remote Similarity	NPD7878	Phase 2
0.5814	Remote Similarity	NPD3074	Discontinued
0.5812	Remote Similarity	NPD7053	Clinical (unspecified phase)
0.5804	Remote Similarity	NPD8104	Phase 3
0.5799	Remote Similarity	NPD8255	Phase 2
0.5795	Remote Similarity	NPD8375	Approved
0.5795	Remote Similarity	NPD8291	Clinical (unspecified phase)
0.5789	Remote Similarity	NPD6525	Clinical (unspecified phase)
0.5788	Remote Similarity	NPD8421	Discontinued
0.5785	Remote Similarity	NPD7712	Clinical (unspecified phase)
0.5784	Remote Similarity	NPD6252	Clinical (unspecified phase)
0.5781	Remote Similarity	NPD5479	Discontinued
0.5777	Remote Similarity	NPD5850	Phase 3
0.5761	Remote Similarity	NPD4130	Phase 3
0.576	Remote Similarity	NPD5632	Approved
0.5759	Remote Similarity	NPD1867	Approved
0.5758	Remote Similarity	NPD5483	Clinical (unspecified phase)
0.5754	Remote Similarity	NPD1955	Discontinued
0.5752	Remote Similarity	NPD8371	Clinical (unspecified phase)
0.5732	Remote Similarity	NPD772	Phase 3
0.573	Remote Similarity	NPD5482	Discontinued
0.5709	Remote Similarity	NPD5416	Discontinued
0.5703	Remote Similarity	NPD5417	Clinical (unspecified phase)
0.5703	Remote Similarity	NPD4897	Phase 2
0.5693	Remote Similarity	NPD4369	Phase 2
0.5685	Remote Similarity	NPD6745	Discontinued
0.5685	Remote Similarity	NPD7605	Discovery
0.5682	Remote Similarity	NPD4322	Discontinued
0.5679	Remote Similarity	NPD5487	Phase 1
0.5678	Remote Similarity	NPD3785	Clinical (unspecified phase)
0.5669	Remote Similarity	NPD8460	Approved
0.5669	Remote Similarity	NPD8459	Approved
0.5667	Remote Similarity	NPD1480	Clinical (unspecified phase)
0.5665	Remote Similarity	NPD7886	Phase 2
0.5665	Remote Similarity	NPD7025	Clinical (unspecified phase)
0.5665	Remote Similarity	NPD7885	Phase 2
0.5664	Remote Similarity	NPD8289	Discontinued
0.566	Remote Similarity	NPD4334	Discontinued
0.5659	Remote Similarity	NPD5022	Discontinued
0.5657	Remote Similarity	NPD3326	Clinical (unspecified phase)
0.5656	Remote Similarity	NPD3946	Clinical (unspecified phase)
0.5654	Remote Similarity	NPD6741	Clinical (unspecified phase)
0.5645	Remote Similarity	NPD7470	Discontinued
0.5644	Remote Similarity	NPD7417	Discontinued
0.5643	Remote Similarity	NPD6249	Phase 2
0.5643	Remote Similarity	NPD3800	Clinical (unspecified phase)
0.5643	Remote Similarity	NPD6248	Phase 2
0.5642	Remote Similarity	NPD3259	Approved
0.5637	Remote Similarity	NPD8372	Clinical (unspecified phase)
0.5634	Remote Similarity	NPD1936	Clinical (unspecified phase)
0.5634	Remote Similarity	NPD4887	Discontinued
0.5632	Remote Similarity	NPD6023	Discontinued
0.5622	Remote Similarity	NPD7573	Discontinued
0.5613	Remote Similarity	NPD2785	Clinical (unspecified phase)
0.5607	Remote Similarity	NPD7689	Approved
0.5605	Remote Similarity	NPD2081	Clinical (unspecified phase)
0.5603	Remote Similarity	NPD5887	Clinical (unspecified phase)
0.5603	Remote Similarity	NPD4516	Clinical (unspecified phase)

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