NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	854.47
Volume:	873.119
LogP:	4.459
LogD:	4.692
LogS:	-4.546
# Rotatable Bonds:	15
TPSA:	209.92
# H-Bond Aceptor:	16
# H-Bond Donor:	2
# Rings:	4
# Heavy Atoms:	16

MedChem Properties

QED Drug-Likeness Score:	0.114
Synthetic Accessibility Score:	7.785
Fsp3:	0.644
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:	-4.789
MDCK Permeability:	7.80392383603612e-06
Pgp-inhibitor:	0.996
Pgp-substrate:	1.0
Human Intestinal Absorption (HIA):	0.287
20% Bioavailability (F20%):	0.054
30% Bioavailability (F30%):	0.996

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.012
Plasma Protein Binding (PPB):	75.44551849365234%
Volume Distribution (VD):	5.157
Pgp-substrate:	11.50550365447998%

ADMET: Metabolism

CYP1A2-inhibitor:	0.016
CYP1A2-substrate:	0.186
CYP2C19-inhibitor:	0.008
CYP2C19-substrate:	0.053
CYP2C9-inhibitor:	0.309
CYP2C9-substrate:	0.022
CYP2D6-inhibitor:	0.013
CYP2D6-substrate:	0.126
CYP3A4-inhibitor:	0.685
CYP3A4-substrate:	0.312

ADMET: Excretion

Clearance (CL):	9.312
Half-life (T1/2):	0.06

ADMET: Toxicity

hERG Blockers:	0.319
Human Hepatotoxicity (H-HT):	0.688
Drug-inuced Liver Injury (DILI):	0.945
AMES Toxicity:	0.007
Rat Oral Acute Toxicity:	0.965
Maximum Recommended Daily Dose:	0.934
Skin Sensitization:	0.037
Carcinogencity:	0.403
Eye Corrosion:	0.003
Eye Irritation:	0.006
Respiratory Toxicity:	0.893

Download Data

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

Natural Product: NPC477219

Natural Product ID:	NPC477219
*Common Name:**	33-Methyltetrahydrohalichondramide
IUPAC Name:	N-[(E,3R,4R,5R,9S,10S)-11-[(10S,11S,12S,16S,20S,21R,24E)-12,16-dihydroxy-10-methoxy-11,21-dimethyl-18-oxo-3,7,19,27-tetraoxa-29,30,31-triazatetracyclo[24.2.1.12,5.16,9]hentriaconta-1(28),2(31),4,6(30),8,24,26(29)-heptaen-20-yl]-4,10-dimethoxy-3,5,9-trimethyl-6-oxoundec-1-enyl]-N-methylformamide
Synonyms:	33-Methyltetrahydrohalichondramide
Standard InCHIKey:	HSWMTNMCGWWOOK-OBOSSNHOSA-N
Standard InCHI:	InChI=1S/C45H66N4O12/c1-27-13-10-11-16-40-46-34(24-58-40)44-48-35(25-60-44)45-47-33(23-59-45)43(57-9)31(5)36(52)15-12-14-32(51)21-41(54)61-39(27)22-38(55-7)28(2)17-18-37(53)30(4)42(56-8)29(3)19-20-49(6)26-50/h11,16,19-20,23-32,36,38-39,42-43,51-52H,10,12-15,17-18,21-22H2,1-9H3/b16-11+,20-19+/t27-,28+,29-,30+,31+,32+,36+,38+,39+,42-,43+/m1/s1
SMILES:	C[C@@H]1CC/C=C/C2=NC(=CO2)C3=NC(=CO3)C4=NC(=CO4)[C@H]([C@H]([C@H](CCC[C@@H](CC(=O)O[C@H]1C[C@@H]([C@@H](C)CCC(=O)[C@H](C)[C@@H]([C@H](C)/C=C/N(C)C=O)OC)OC)O)O)C)OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	n.a.
PubChem CID:	45268860
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001283] Terpene lactones [CHEMONTID:0001538] Diterpene lactones

*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
NPO10690	Hexabranchus sanguineus	Species	Hexabranchidae	Eukaryota	n.a.	n.a.	n.a.	PMID[19254038]
NPO10690	Hexabranchus sanguineus	Species	Hexabranchidae	Eukaryota	n.a.	n.a.	n.a.	PMID[28098996]
NPO10690	Hexabranchus sanguineus	Species	Hexabranchidae	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
MIC	3

Activity Type	# Activity
Organism	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT20	Organism	Candida albicans	Candida albicans	MIC	=	0.25	ug/ml	PMID[19254038]
NPT554	Organism	Candida glabrata	Candida glabrata	MIC	=	0.125	ug/ml	PMID[19254038]
NPT85	Organism	Filobasidiella neoformans	Cryptococcus neoformans	MIC	=	0.5	ug/ml	PMID[19254038]

☑ 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 NPC477219 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	258
0.1-0.2	1535
0.2-0.3	8075
0.3-0.4	20511
0.4-0.5	11022
0.5-0.6	1196
0.6-0.7	52
0.7-0.8	15
0.8-0.85	2
0.85-0.9	5
0.9-0.95	4
0.95-1	22

Similarity Score	Similarity Level	Natural Product ID
0.995	High Similarity	NPC37924
0.99	High Similarity	NPC325683
0.9802	High Similarity	NPC476828
0.9755	High Similarity	NPC177432
0.9755	High Similarity	NPC299035
0.9707	High Similarity	NPC322800
0.9707	High Similarity	NPC477218
0.9707	High Similarity	NPC168135
0.9653	High Similarity	NPC476826
0.9653	High Similarity	NPC476827
0.9653	High Similarity	NPC476831
0.9606	High Similarity	NPC476830
0.9048	High Similarity	NPC476832
0.8164	Intermediate Similarity	NPC476829
0.744	Intermediate Similarity	NPC314523
0.744	Intermediate Similarity	NPC58001
0.7327	Intermediate Similarity	NPC224395
0.7327	Intermediate Similarity	NPC208297
0.7291	Intermediate Similarity	NPC30527
0.7207	Intermediate Similarity	NPC258022
0.7155	Intermediate Similarity	NPC477588
0.7155	Intermediate Similarity	NPC477585
0.7155	Intermediate Similarity	NPC477586
0.7155	Intermediate Similarity	NPC477590
0.7123	Intermediate Similarity	NPC107458
0.7123	Intermediate Similarity	NPC295653
0.7097	Intermediate Similarity	NPC58112
0.7097	Intermediate Similarity	NPC88938
0.7097	Intermediate Similarity	NPC306300
0.7071	Intermediate Similarity	NPC477587
0.7071	Intermediate Similarity	NPC477589
0.6982	Remote Similarity	NPC48323
0.6982	Remote Similarity	NPC289029
0.6895	Remote Similarity	NPC199461
0.6895	Remote Similarity	NPC46313
0.6895	Remote Similarity	NPC103452
0.6824	Remote Similarity	NPC49195
0.6742	Remote Similarity	NPC315411
0.6681	Remote Similarity	NPC309919
0.6667	Remote Similarity	NPC472436
0.6652	Remote Similarity	NPC315872
0.6568	Remote Similarity	NPC315061
0.6549	Remote Similarity	NPC472435
0.653	Remote Similarity	NPC314222
0.653	Remote Similarity	NPC196449
0.6476	Remote Similarity	NPC211555
0.6457	Remote Similarity	NPC165964
0.6429	Remote Similarity	NPC186452
0.6423	Remote Similarity	NPC102593
0.6423	Remote Similarity	NPC196718
0.6308	Remote Similarity	NPC12660
0.6308	Remote Similarity	NPC258048
0.6299	Remote Similarity	NPC472434
0.6279	Remote Similarity	NPC54983
0.6275	Remote Similarity	NPC72715
0.627	Remote Similarity	NPC314633
0.625	Remote Similarity	NPC161801
0.6245	Remote Similarity	NPC148889
0.6206	Remote Similarity	NPC207620
0.6203	Remote Similarity	NPC471979
0.6184	Remote Similarity	NPC169716
0.6175	Remote Similarity	NPC182222
0.6173	Remote Similarity	NPC315804
0.6173	Remote Similarity	NPC313804
0.6133	Remote Similarity	NPC316224
0.609	Remote Similarity	NPC471978
0.6085	Remote Similarity	NPC58209
0.6077	Remote Similarity	NPC10904
0.6075	Remote Similarity	NPC473833
0.6074	Remote Similarity	NPC477979
0.6071	Remote Similarity	NPC141053
0.6067	Remote Similarity	NPC152620
0.6064	Remote Similarity	NPC140296
0.6064	Remote Similarity	NPC186351
0.605	Remote Similarity	NPC316403
0.6048	Remote Similarity	NPC97746
0.6031	Remote Similarity	NPC124300
0.603	Remote Similarity	NPC328928
0.6026	Remote Similarity	NPC220408
0.6023	Remote Similarity	NPC53534
0.6023	Remote Similarity	NPC310618
0.6008	Remote Similarity	NPC471015
0.6008	Remote Similarity	NPC291609
0.6008	Remote Similarity	NPC205372
0.6	Remote Similarity	NPC131885
0.5985	Remote Similarity	NPC475301
0.5985	Remote Similarity	NPC326930
0.5976	Remote Similarity	NPC298436
0.5975	Remote Similarity	NPC269367
0.5963	Remote Similarity	NPC470042
0.5962	Remote Similarity	NPC13603
0.5954	Remote Similarity	NPC26543
0.5945	Remote Similarity	NPC220852
0.5925	Remote Similarity	NPC85879
0.5925	Remote Similarity	NPC53255
0.5923	Remote Similarity	NPC148896
0.5923	Remote Similarity	NPC180668
0.5923	Remote Similarity	NPC471013
0.5913	Remote Similarity	NPC194740
0.5911	Remote Similarity	NPC230683
0.5911	Remote Similarity	NPC209981
0.5907	Remote Similarity	NPC166712
0.5885	Remote Similarity	NPC146418
0.5885	Remote Similarity	NPC75179
0.5885	Remote Similarity	NPC208364
0.5885	Remote Similarity	NPC160100
0.5885	Remote Similarity	NPC188400
0.5878	Remote Similarity	NPC16066
0.5875	Remote Similarity	NPC240384
0.5875	Remote Similarity	NPC285343
0.5873	Remote Similarity	NPC244536
0.5871	Remote Similarity	NPC67401
0.587	Remote Similarity	NPC314270
0.5859	Remote Similarity	NPC34770
0.5856	Remote Similarity	NPC63971
0.5856	Remote Similarity	NPC91868
0.5853	Remote Similarity	NPC474183
0.5836	Remote Similarity	NPC185197
0.5833	Remote Similarity	NPC203373
0.583	Remote Similarity	NPC312645
0.5826	Remote Similarity	NPC287208
0.5823	Remote Similarity	NPC323969
0.5817	Remote Similarity	NPC324619
0.5817	Remote Similarity	NPC475315
0.5814	Remote Similarity	NPC184680
0.5811	Remote Similarity	NPC313587
0.5811	Remote Similarity	NPC316110
0.5811	Remote Similarity	NPC256912
0.5811	Remote Similarity	NPC315893
0.5809	Remote Similarity	NPC472286
0.5809	Remote Similarity	NPC472287
0.5804	Remote Similarity	NPC260434
0.5797	Remote Similarity	NPC314254
0.5797	Remote Similarity	NPC313966
0.5795	Remote Similarity	NPC173250
0.5794	Remote Similarity	NPC212766
0.5794	Remote Similarity	NPC289423
0.5792	Remote Similarity	NPC470785
0.5792	Remote Similarity	NPC470784
0.5792	Remote Similarity	NPC317572
0.5788	Remote Similarity	NPC227824
0.5784	Remote Similarity	NPC120513
0.5779	Remote Similarity	NPC314834
0.5779	Remote Similarity	NPC475533
0.5777	Remote Similarity	NPC478141
0.5775	Remote Similarity	NPC57453
0.5769	Remote Similarity	NPC168922
0.5768	Remote Similarity	NPC472259
0.5768	Remote Similarity	NPC329982
0.5762	Remote Similarity	NPC476514
0.5759	Remote Similarity	NPC284888
0.5758	Remote Similarity	NPC1608
0.5756	Remote Similarity	NPC282346
0.5756	Remote Similarity	NPC187558
0.5756	Remote Similarity	NPC18487
0.5752	Remote Similarity	NPC473800
0.5752	Remote Similarity	NPC181081
0.5752	Remote Similarity	NPC475455
0.5749	Remote Similarity	NPC153452
0.5747	Remote Similarity	NPC99891
0.5744	Remote Similarity	NPC313345
0.5744	Remote Similarity	NPC313796
0.5744	Remote Similarity	NPC315638
0.5744	Remote Similarity	NPC314855
0.5743	Remote Similarity	NPC281049
0.5742	Remote Similarity	NPC14288
0.5742	Remote Similarity	NPC217176
0.574	Remote Similarity	NPC34319
0.5731	Remote Similarity	NPC473449
0.5731	Remote Similarity	NPC101350
0.5726	Remote Similarity	NPC85702
0.5725	Remote Similarity	NPC101312
0.5725	Remote Similarity	NPC473639
0.572	Remote Similarity	NPC471004
0.572	Remote Similarity	NPC321592
0.572	Remote Similarity	NPC54803
0.572	Remote Similarity	NPC314297
0.572	Remote Similarity	NPC315545
0.5714	Remote Similarity	NPC123839
0.5714	Remote Similarity	NPC102008
0.5709	Remote Similarity	NPC89508
0.5709	Remote Similarity	NPC319232
0.5709	Remote Similarity	NPC24370
0.5703	Remote Similarity	NPC322135
0.5703	Remote Similarity	NPC223409
0.5699	Remote Similarity	NPC215837
0.5698	Remote Similarity	NPC329631
0.5697	Remote Similarity	NPC128115
0.5697	Remote Similarity	NPC54066
0.5693	Remote Similarity	NPC100734
0.5693	Remote Similarity	NPC315634
0.5693	Remote Similarity	NPC88923
0.5692	Remote Similarity	NPC235685
0.5692	Remote Similarity	NPC28945
0.5692	Remote Similarity	NPC15801
0.5683	Remote Similarity	NPC129897
0.568	Remote Similarity	NPC303658
0.5678	Remote Similarity	NPC192306
0.5676	Remote Similarity	NPC475619
0.5675	Remote Similarity	NPC90019

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 NPC477219 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	166
0.1-0.2	526
0.2-0.3	1676
0.3-0.4	3663
0.4-0.5	2736
0.5-0.6	366
0.6-0.7	16
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
0.7091	Intermediate Similarity	NPD7896	Approved
0.6652	Remote Similarity	NPD6444	Clinical (unspecified phase)
0.6533	Remote Similarity	NPD6347	Phase 2
0.6513	Remote Similarity	NPD6974	Phase 3
0.6478	Remote Similarity	NPD7853	Phase 2
0.6449	Remote Similarity	NPD7284	Clinical (unspecified phase)
0.6432	Remote Similarity	NPD7490	Discontinued
0.6381	Remote Similarity	NPD8370	Discontinued
0.6356	Remote Similarity	NPD7031	Phase 1
0.6337	Remote Similarity	NPD7547	Clinical (unspecified phase)
0.6318	Remote Similarity	NPD2433	Clinical (unspecified phase)
0.6281	Remote Similarity	NPD7180	Phase 3
0.6223	Remote Similarity	NPD2779	Approved
0.6208	Remote Similarity	NPD4667	Clinical (unspecified phase)
0.6206	Remote Similarity	NPD7690	Clinical (unspecified phase)
0.6179	Remote Similarity	NPD6247	Clinical (unspecified phase)
0.6145	Remote Similarity	NPD4898	Clinical (unspecified phase)
0.6126	Remote Similarity	NPD4368	Phase 2
0.6111	Remote Similarity	NPD5922	Phase 3
0.6102	Remote Similarity	NPD4394	Clinical (unspecified phase)
0.6098	Remote Similarity	NPD8356	Approved
0.6094	Remote Similarity	NPD8117	Approved
0.6094	Remote Similarity	NPD2778	Approved
0.6094	Remote Similarity	NPD8116	Phase 3
0.6089	Remote Similarity	NPD3263	Phase 3
0.608	Remote Similarity	NPD5924	Discontinued
0.6064	Remote Similarity	NPD8430	Approved
0.6047	Remote Similarity	NPD2951	Discontinued
0.6042	Remote Similarity	NPD3392	Approved
0.6038	Remote Similarity	NPD8324	Phase 2
0.6033	Remote Similarity	NPD3945	Discontinued
0.6031	Remote Similarity	NPD7022	Phase 2
0.6025	Remote Similarity	NPD5443	Clinical (unspecified phase)
0.6024	Remote Similarity	NPD5640	Discontinued
0.6023	Remote Similarity	NPD8255	Phase 2
0.6017	Remote Similarity	NPD6567	Clinical (unspecified phase)
0.6016	Remote Similarity	NPD5908	Clinical (unspecified phase)
0.6015	Remote Similarity	NPD6525	Clinical (unspecified phase)
0.6008	Remote Similarity	NPD5532	Phase 2
0.6008	Remote Similarity	NPD6169	Phase 1
0.6	Remote Similarity	NPD4958	Clinical (unspecified phase)
0.6	Remote Similarity	NPD7268	Clinical (unspecified phase)
0.5992	Remote Similarity	NPD5866	Approved
0.5977	Remote Similarity	NPD3801	Clinical (unspecified phase)
0.5973	Remote Similarity	NPD8279	Clinical (unspecified phase)
0.5961	Remote Similarity	NPD3006	Discontinued
0.5957	Remote Similarity	NPD6857	Phase 3
0.5954	Remote Similarity	NPD5482	Discontinued
0.5953	Remote Similarity	NPD2921	Clinical (unspecified phase)
0.5951	Remote Similarity	NPD8479	Phase 2
0.5945	Remote Similarity	NPD4373	Phase 2
0.5943	Remote Similarity	NPD5293	Phase 2
0.5943	Remote Similarity	NPD1638	Discovery
0.5941	Remote Similarity	NPD7393	Clinical (unspecified phase)
0.5941	Remote Similarity	NPD3507	Phase 2
0.5925	Remote Similarity	NPD8246	Approved
0.5925	Remote Similarity	NPD8247	Approved
0.5922	Remote Similarity	NPD3074	Discontinued
0.5904	Remote Similarity	NPD6824	Clinical (unspecified phase)
0.59	Remote Similarity	NPD8291	Clinical (unspecified phase)
0.59	Remote Similarity	NPD8375	Approved
0.5889	Remote Similarity	NPD7589	Clinical (unspecified phase)
0.5889	Remote Similarity	NPD4952	Phase 3
0.5887	Remote Similarity	NPD8463	Approved
0.5887	Remote Similarity	NPD5850	Phase 3
0.5873	Remote Similarity	NPD4086	Phase 1
0.5869	Remote Similarity	NPD7417	Discontinued
0.5866	Remote Similarity	NPD1867	Approved
0.5856	Remote Similarity	NPD8371	Clinical (unspecified phase)
0.5851	Remote Similarity	NPD4392	Phase 2
0.585	Remote Similarity	NPD8104	Phase 3
0.5846	Remote Similarity	NPD6716	Phase 1
0.583	Remote Similarity	NPD7885	Phase 2
0.583	Remote Similarity	NPD7886	Phase 2
0.5827	Remote Similarity	NPD6252	Clinical (unspecified phase)
0.5827	Remote Similarity	NPD1480	Clinical (unspecified phase)
0.5827	Remote Similarity	NPD8374	Phase 3
0.5824	Remote Similarity	NPD6495	Clinical (unspecified phase)
0.581	Remote Similarity	NPD7994	Phase 2
0.5806	Remote Similarity	NPD7878	Phase 2
0.5804	Remote Similarity	NPD1505	Phase 2
0.5802	Remote Similarity	NPD5483	Clinical (unspecified phase)
0.5798	Remote Similarity	NPD8329	Phase 3
0.5797	Remote Similarity	NPD7053	Clinical (unspecified phase)
0.5795	Remote Similarity	NPD1955	Discontinued
0.5795	Remote Similarity	NPD4369	Phase 2
0.5789	Remote Similarity	NPD8160	Phase 2
0.5781	Remote Similarity	NPD772	Phase 3
0.5779	Remote Similarity	NPD4900	Clinical (unspecified phase)
0.5765	Remote Similarity	NPD5479	Discontinued
0.5765	Remote Similarity	NPD1659	Phase 1
0.5751	Remote Similarity	NPD5450	Discontinued
0.573	Remote Similarity	NPD5857	Phase 3
0.573	Remote Similarity	NPD6023	Discontinued
0.5725	Remote Similarity	NPD4322	Discontinued
0.572	Remote Similarity	NPD5817	Discontinued
0.572	Remote Similarity	NPD7796	Approved
0.572	Remote Similarity	NPD7797	Approved
0.5719	Remote Similarity	NPD8421	Discontinued
0.5714	Remote Similarity	NPD53	Approved
0.5714	Remote Similarity	NPD7777	Approved
0.5714	Remote Similarity	NPD7778	Approved
0.5709	Remote Similarity	NPD8289	Discontinued
0.5709	Remote Similarity	NPD5887	Clinical (unspecified phase)
0.5709	Remote Similarity	NPD1927	Discontinued
0.5703	Remote Similarity	NPD8327	Clinical (unspecified phase)
0.5703	Remote Similarity	NPD8326	Phase 3
0.5703	Remote Similarity	NPD8325	Phase 3
0.5698	Remote Similarity	NPD6741	Clinical (unspecified phase)
0.5694	Remote Similarity	NPD8107	Approved
0.5693	Remote Similarity	NPD7803	Approved
0.5691	Remote Similarity	NPD7070	Clinical (unspecified phase)
0.5691	Remote Similarity	NPD7703	Clinical (unspecified phase)
0.5691	Remote Similarity	NPD5416	Discontinued
0.5686	Remote Similarity	NPD3259	Approved
0.5681	Remote Similarity	NPD6962	Phase 2
0.568	Remote Similarity	NPD5632	Approved
0.5679	Remote Similarity	NPD8108	Approved
0.5674	Remote Similarity	NPD7416	Clinical (unspecified phase)
0.5662	Remote Similarity	NPD7708	Approved
0.566	Remote Similarity	NPD8359	Phase 2
0.5658	Remote Similarity	NPD6627	Discontinued
0.5654	Remote Similarity	NPD8460	Approved
0.5654	Remote Similarity	NPD8459	Approved
0.5651	Remote Similarity	NPD8253	Phase 3
0.565	Remote Similarity	NPD1166	Clinical (unspecified phase)
0.565	Remote Similarity	NPD5726	Clinical (unspecified phase)
0.5641	Remote Similarity	NPD4334	Discontinued
0.5628	Remote Similarity	NPD7470	Discontinued
0.5627	Remote Similarity	NPD5499	Approved
0.5627	Remote Similarity	NPD6790	Phase 1
0.5625	Remote Similarity	NPD7955	Approved
0.5625	Remote Similarity	NPD7956	Approved
0.5622	Remote Similarity	NPD7538	Clinical (unspecified phase)
0.5622	Remote Similarity	NPD5417	Clinical (unspecified phase)
0.562	Remote Similarity	NPD8372	Clinical (unspecified phase)
0.562	Remote Similarity	NPD5461	Discontinued
0.5618	Remote Similarity	NPD4896	Clinical (unspecified phase)
0.5618	Remote Similarity	NPD6231	Phase 3
0.5618	Remote Similarity	NPD6198	Phase 1
0.5615	Remote Similarity	NPD4901	Clinical (unspecified phase)
0.5609	Remote Similarity	NPD8049	Phase 2
0.5605	Remote Similarity	NPD8097	Phase 3
0.5605	Remote Similarity	NPD8096	Phase 3
0.5605	Remote Similarity	NPD7605	Discovery
0.5603	Remote Similarity	NPD7710	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