NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	838.44
Volume:	853.186
LogP:	3.281
LogD:	3.351
LogS:	-4.925
# Rotatable Bonds:	15
TPSA:	206.76
# H-Bond Aceptor:	16
# H-Bond Donor:	1
# Rings:	4
# Heavy Atoms:	16

MedChem Properties

QED Drug-Likeness Score:	0.119
Synthetic Accessibility Score:	7.661
Fsp3:	0.614
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:	-4.733
MDCK Permeability:	6.4858500081754755e-06
Pgp-inhibitor:	0.996
Pgp-substrate:	0.998
Human Intestinal Absorption (HIA):	0.169
20% Bioavailability (F20%):	0.007
30% Bioavailability (F30%):	0.991

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.009
Plasma Protein Binding (PPB):	75.07141876220703%
Volume Distribution (VD):	5.954
Pgp-substrate:	2.5198299884796143%

ADMET: Metabolism

CYP1A2-inhibitor:	0.006
CYP1A2-substrate:	0.213
CYP2C19-inhibitor:	0.009
CYP2C19-substrate:	0.047
CYP2C9-inhibitor:	0.293
CYP2C9-substrate:	0.044
CYP2D6-inhibitor:	0.006
CYP2D6-substrate:	0.433
CYP3A4-inhibitor:	0.71
CYP3A4-substrate:	0.307

ADMET: Excretion

Clearance (CL):	10.037
Half-life (T1/2):	0.068

ADMET: Toxicity

hERG Blockers:	0.015
Human Hepatotoxicity (H-HT):	0.874
Drug-inuced Liver Injury (DILI):	0.957
AMES Toxicity:	0.004
Rat Oral Acute Toxicity:	1.0
Maximum Recommended Daily Dose:	0.879
Skin Sensitization:	0.013
Carcinogencity:	0.641
Eye Corrosion:	0.003
Eye Irritation:	0.004
Respiratory Toxicity:	0.015

Download Data

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

Natural Product: NPC476827

Natural Product ID:	NPC476827
*Common Name:**	Dihydrohalichondramide
IUPAC Name:	N-[(E)-11-[(24E)-16-hydroxy-10-methoxy-11,21-dimethyl-12,18-dioxo-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-5,9-dimethyl-6-oxoundec-1-enyl]-N-methylformamide
Synonyms:	Dihydrohalichondramide
Standard InCHIKey:	YOEZYKWLOADELV-APXUAPHXSA-N
Standard InCHI:	InChI=1S/C44H62N4O12/c1-27-13-9-10-17-40-45-33(24-57-40)43-47-34(25-59-43)44-46-32(23-58-44)42(56-8)30(4)35(51)15-11-14-31(50)21-41(53)60-39(27)22-38(55-7)28(2)18-19-36(52)29(3)37(54-6)16-12-20-48(5)26-49/h10,12,17,20,23-31,37-39,42,50H,9,11,13-16,18-19,21-22H2,1-8H3/b17-10+,20-12+
SMILES:	CC1CC/C=C/C2=NC(=CO2)C3=NC(=CO3)C4=NC(=CO4)C(C(C(=O)CCCC(CC(=O)OC1CC(C(C)CCC(=O)C(C)C(C/C=C/N(C)C=O)OC)OC)O)C)OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	n.a.
PubChem CID:	10259927
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
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	3

Activity Type	# Activity
Cell Line	1
Organism	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT111	Cell Line	K562	Homo sapiens	LC50	=	0.32	ug/ml	PMID[15568783]
NPT20	Organism	Candida albicans	Candida albicans	IZ	=	19	mm	PMID[15568783]
NPT21	Organism	Aspergillus niger	Aspergillus niger	IZ	=	11	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 NPC476827 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	257
0.1-0.2	1610
0.2-0.3	9155
0.3-0.4	22064
0.4-0.5	8570
0.5-0.6	953
0.6-0.7	45
0.7-0.8	12
0.8-0.85	0
0.85-0.9	3
0.9-0.95	11
0.95-1	17

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC476831
1.0	High Similarity	NPC476826
0.995	High Similarity	NPC476830
0.9851	High Similarity	NPC476828
0.9653	High Similarity	NPC477219
0.9606	High Similarity	NPC37924
0.9559	High Similarity	NPC325683
0.942	High Similarity	NPC177432
0.942	High Similarity	NPC299035
0.9375	High Similarity	NPC322800
0.9375	High Similarity	NPC477218
0.9375	High Similarity	NPC168135
0.9369	High Similarity	NPC476832
0.8473	Intermediate Similarity	NPC476829
0.7225	Intermediate Similarity	NPC58001
0.7225	Intermediate Similarity	NPC314523
0.7185	Intermediate Similarity	NPC477586
0.7185	Intermediate Similarity	NPC477590
0.7185	Intermediate Similarity	NPC477588
0.7185	Intermediate Similarity	NPC477585
0.7123	Intermediate Similarity	NPC224395
0.7123	Intermediate Similarity	NPC208297
0.7101	Intermediate Similarity	NPC477589
0.7101	Intermediate Similarity	NPC477587
0.7073	Intermediate Similarity	NPC30527
0.7009	Intermediate Similarity	NPC258022
0.6923	Remote Similarity	NPC107458
0.6923	Remote Similarity	NPC295653
0.6895	Remote Similarity	NPC306300
0.6895	Remote Similarity	NPC88938
0.6895	Remote Similarity	NPC58112
0.6853	Remote Similarity	NPC49195
0.6786	Remote Similarity	NPC289029
0.6786	Remote Similarity	NPC48323
0.6767	Remote Similarity	NPC315411
0.6697	Remote Similarity	NPC103452
0.6697	Remote Similarity	NPC199461
0.6697	Remote Similarity	NPC46313
0.6681	Remote Similarity	NPC315872
0.6593	Remote Similarity	NPC315061
0.6507	Remote Similarity	NPC211555
0.6498	Remote Similarity	NPC309919
0.6498	Remote Similarity	NPC472436
0.6459	Remote Similarity	NPC186452
0.6449	Remote Similarity	NPC196718
0.6449	Remote Similarity	NPC102593
0.6381	Remote Similarity	NPC472435
0.637	Remote Similarity	NPC314222
0.637	Remote Similarity	NPC196449
0.6353	Remote Similarity	NPC165964
0.6338	Remote Similarity	NPC12660
0.6308	Remote Similarity	NPC54983
0.6296	Remote Similarity	NPC314633
0.6235	Remote Similarity	NPC72715
0.6211	Remote Similarity	NPC161801
0.6207	Remote Similarity	NPC258048
0.6132	Remote Similarity	NPC315804
0.6132	Remote Similarity	NPC313804
0.61	Remote Similarity	NPC477979
0.6094	Remote Similarity	NPC316224
0.607	Remote Similarity	NPC472434
0.6056	Remote Similarity	NPC207620
0.6035	Remote Similarity	NPC169716
0.6032	Remote Similarity	NPC205372
0.6032	Remote Similarity	NPC141053
0.6025	Remote Similarity	NPC131885
0.6024	Remote Similarity	NPC186351
0.6016	Remote Similarity	NPC148889
0.6008	Remote Similarity	NPC316403
0.6	Remote Similarity	NPC269367
0.5985	Remote Similarity	NPC471979
0.5977	Remote Similarity	NPC473833
0.5945	Remote Similarity	NPC182222
0.5936	Remote Similarity	NPC194740
0.5933	Remote Similarity	NPC328928
0.5923	Remote Similarity	NPC58209
0.5916	Remote Similarity	NPC10904
0.5907	Remote Similarity	NPC75179
0.5906	Remote Similarity	NPC220852
0.5902	Remote Similarity	NPC16066
0.5898	Remote Similarity	NPC240384
0.5896	Remote Similarity	NPC140296
0.5894	Remote Similarity	NPC314270
0.5887	Remote Similarity	NPC475301
0.5887	Remote Similarity	NPC326930
0.588	Remote Similarity	NPC97746
0.5878	Remote Similarity	NPC91868
0.5878	Remote Similarity	NPC85702
0.5878	Remote Similarity	NPC63971
0.5874	Remote Similarity	NPC230683
0.5874	Remote Similarity	NPC471978
0.5869	Remote Similarity	NPC124300
0.5865	Remote Similarity	NPC53534
0.5862	Remote Similarity	NPC310618
0.5852	Remote Similarity	NPC152620
0.5849	Remote Similarity	NPC471015
0.5847	Remote Similarity	NPC323969
0.5846	Remote Similarity	NPC291609
0.5837	Remote Similarity	NPC256912
0.5837	Remote Similarity	NPC285343
0.5827	Remote Similarity	NPC53255
0.5827	Remote Similarity	NPC260434
0.5827	Remote Similarity	NPC85879
0.5816	Remote Similarity	NPC317572
0.5814	Remote Similarity	NPC101350
0.5814	Remote Similarity	NPC474183
0.5806	Remote Similarity	NPC298436
0.5805	Remote Similarity	NPC13603
0.5799	Remote Similarity	NPC185197
0.5792	Remote Similarity	NPC472259
0.5789	Remote Similarity	NPC312645
0.5785	Remote Similarity	NPC287208
0.5781	Remote Similarity	NPC220408
0.5781	Remote Similarity	NPC284888
0.5781	Remote Similarity	NPC329631
0.5775	Remote Similarity	NPC235685
0.5775	Remote Similarity	NPC184680
0.5774	Remote Similarity	NPC181081
0.5774	Remote Similarity	NPC315893
0.5774	Remote Similarity	NPC313587
0.5774	Remote Similarity	NPC316110
0.5768	Remote Similarity	NPC314855
0.5768	Remote Similarity	NPC472286
0.5768	Remote Similarity	NPC313345
0.5768	Remote Similarity	NPC315638
0.5768	Remote Similarity	NPC313796
0.5768	Remote Similarity	NPC472287
0.5766	Remote Similarity	NPC34319
0.5765	Remote Similarity	NPC14288
0.5763	Remote Similarity	NPC180668
0.5763	Remote Similarity	NPC471013
0.5763	Remote Similarity	NPC148896
0.5755	Remote Similarity	NPC473493
0.5753	Remote Similarity	NPC470785
0.5753	Remote Similarity	NPC470784
0.5751	Remote Similarity	NPC470042
0.5747	Remote Similarity	NPC166712
0.5744	Remote Similarity	NPC314297
0.5744	Remote Similarity	NPC315545
0.5738	Remote Similarity	NPC123839
0.5737	Remote Similarity	NPC478141
0.5736	Remote Similarity	NPC26543
0.5731	Remote Similarity	NPC24370
0.5731	Remote Similarity	NPC319232
0.5725	Remote Similarity	NPC208364
0.5725	Remote Similarity	NPC322135
0.5725	Remote Similarity	NPC188400
0.5725	Remote Similarity	NPC160100
0.572	Remote Similarity	NPC475315
0.572	Remote Similarity	NPC128115
0.572	Remote Similarity	NPC324619
0.5714	Remote Similarity	NPC18487
0.5714	Remote Similarity	NPC187558
0.5714	Remote Similarity	NPC146418
0.5709	Remote Similarity	NPC244536
0.5708	Remote Similarity	NPC143977
0.5703	Remote Similarity	NPC303658
0.5699	Remote Similarity	NPC209981
0.5698	Remote Similarity	NPC34770
0.5698	Remote Similarity	NPC475619
0.5697	Remote Similarity	NPC162860
0.5697	Remote Similarity	NPC478158
0.5693	Remote Similarity	NPC227824
0.5686	Remote Similarity	NPC100547
0.5682	Remote Similarity	NPC475533
0.5681	Remote Similarity	NPC475196
0.568	Remote Similarity	NPC288987
0.5677	Remote Similarity	NPC203373
0.5673	Remote Similarity	NPC314834
0.5668	Remote Similarity	NPC89508
0.5664	Remote Similarity	NPC95240
0.5664	Remote Similarity	NPC223409
0.5659	Remote Similarity	NPC323752
0.5656	Remote Similarity	NPC266249
0.5655	Remote Similarity	NPC67401
0.5654	Remote Similarity	NPC28945
0.5654	Remote Similarity	NPC15801
0.5647	Remote Similarity	NPC118559
0.5647	Remote Similarity	NPC34580
0.5647	Remote Similarity	NPC261251
0.5647	Remote Similarity	NPC124920
0.5647	Remote Similarity	NPC304307
0.5646	Remote Similarity	NPC315499
0.5645	Remote Similarity	NPC478157
0.564	Remote Similarity	NPC281049
0.5639	Remote Similarity	NPC173250
0.5636	Remote Similarity	NPC192306
0.5633	Remote Similarity	NPC107077
0.5633	Remote Similarity	NPC223791
0.5632	Remote Similarity	NPC478029
0.5631	Remote Similarity	NPC222391
0.563	Remote Similarity	NPC212766
0.563	Remote Similarity	NPC120513
0.563	Remote Similarity	NPC122886
0.563	Remote Similarity	NPC289423
0.562	Remote Similarity	NPC54803
0.562	Remote Similarity	NPC321592
0.5618	Remote Similarity	NPC260909
0.5615	Remote Similarity	NPC54420
0.5615	Remote Similarity	NPC57453

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 NPC476827 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	538
0.2-0.3	1660
0.3-0.4	3745
0.4-0.5	2681
0.5-0.6	342
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
0.6892	Remote Similarity	NPD7896	Approved
0.6681	Remote Similarity	NPD6444	Clinical (unspecified phase)
0.6504	Remote Similarity	NPD7853	Phase 2
0.6489	Remote Similarity	NPD6347	Phase 2
0.6449	Remote Similarity	NPD7031	Phase 1
0.6408	Remote Similarity	NPD7284	Clinical (unspecified phase)
0.6388	Remote Similarity	NPD7490	Discontinued
0.6364	Remote Similarity	NPD7547	Clinical (unspecified phase)
0.6333	Remote Similarity	NPD6974	Phase 3
0.6307	Remote Similarity	NPD7180	Phase 3
0.625	Remote Similarity	NPD5443	Clinical (unspecified phase)
0.625	Remote Similarity	NPD2779	Approved
0.6234	Remote Similarity	NPD4667	Clinical (unspecified phase)
0.6208	Remote Similarity	NPD2433	Clinical (unspecified phase)
0.6204	Remote Similarity	NPD6247	Clinical (unspecified phase)
0.6169	Remote Similarity	NPD4898	Clinical (unspecified phase)
0.6154	Remote Similarity	NPD8370	Discontinued
0.6151	Remote Similarity	NPD4368	Phase 2
0.6134	Remote Similarity	NPD5922	Phase 3
0.6126	Remote Similarity	NPD4394	Clinical (unspecified phase)
0.6121	Remote Similarity	NPD2778	Approved
0.6082	Remote Similarity	NPD7393	Clinical (unspecified phase)
0.6071	Remote Similarity	NPD2951	Discontinued
0.6067	Remote Similarity	NPD3392	Approved
0.6058	Remote Similarity	NPD3945	Discontinued
0.6057	Remote Similarity	NPD8356	Approved
0.6056	Remote Similarity	NPD7690	Clinical (unspecified phase)
0.6055	Remote Similarity	NPD8116	Phase 3
0.6055	Remote Similarity	NPD8117	Approved
0.6042	Remote Similarity	NPD6567	Clinical (unspecified phase)
0.6033	Remote Similarity	NPD6169	Phase 1
0.6024	Remote Similarity	NPD4958	Clinical (unspecified phase)
0.6024	Remote Similarity	NPD7268	Clinical (unspecified phase)
0.6024	Remote Similarity	NPD8430	Approved
0.6017	Remote Similarity	NPD5866	Approved
0.6	Remote Similarity	NPD8324	Phase 2
0.6	Remote Similarity	NPD3801	Clinical (unspecified phase)
0.5992	Remote Similarity	NPD7022	Phase 2
0.5983	Remote Similarity	NPD6857	Phase 3
0.5976	Remote Similarity	NPD8479	Phase 2
0.597	Remote Similarity	NPD8463	Approved
0.597	Remote Similarity	NPD5532	Phase 2
0.5968	Remote Similarity	NPD4373	Phase 2
0.5967	Remote Similarity	NPD5293	Phase 2
0.5967	Remote Similarity	NPD1638	Discovery
0.5966	Remote Similarity	NPD3507	Phase 2
0.5947	Remote Similarity	NPD8246	Approved
0.5947	Remote Similarity	NPD8247	Approved
0.5927	Remote Similarity	NPD6824	Clinical (unspecified phase)
0.5914	Remote Similarity	NPD2921	Clinical (unspecified phase)
0.5913	Remote Similarity	NPD1659	Phase 1
0.5913	Remote Similarity	NPD4952	Phase 3
0.5913	Remote Similarity	NPD5924	Discontinued
0.5911	Remote Similarity	NPD5850	Phase 3
0.5889	Remote Similarity	NPD1867	Approved
0.5884	Remote Similarity	NPD8279	Clinical (unspecified phase)
0.5875	Remote Similarity	NPD4392	Phase 2
0.5869	Remote Similarity	NPD6716	Phase 1
0.5857	Remote Similarity	NPD3263	Phase 3
0.5856	Remote Similarity	NPD6525	Clinical (unspecified phase)
0.5853	Remote Similarity	NPD5908	Clinical (unspecified phase)
0.585	Remote Similarity	NPD7589	Clinical (unspecified phase)
0.5849	Remote Similarity	NPD1480	Clinical (unspecified phase)
0.5846	Remote Similarity	NPD6495	Clinical (unspecified phase)
0.5833	Remote Similarity	NPD7994	Phase 2
0.5818	Remote Similarity	NPD7053	Clinical (unspecified phase)
0.5817	Remote Similarity	NPD4369	Phase 2
0.5816	Remote Similarity	NPD1955	Discontinued
0.5813	Remote Similarity	NPD8160	Phase 2
0.5808	Remote Similarity	NPD4322	Discontinued
0.5805	Remote Similarity	NPD8255	Phase 2
0.5805	Remote Similarity	NPD772	Phase 3
0.5798	Remote Similarity	NPD3006	Discontinued
0.5794	Remote Similarity	NPD5640	Discontinued
0.5789	Remote Similarity	NPD6252	Clinical (unspecified phase)
0.5787	Remote Similarity	NPD5479	Discontinued
0.5781	Remote Similarity	NPD6741	Clinical (unspecified phase)
0.5771	Remote Similarity	NPD3259	Approved
0.5766	Remote Similarity	NPD7878	Phase 2
0.5765	Remote Similarity	NPD6962	Phase 2
0.5763	Remote Similarity	NPD5483	Clinical (unspecified phase)
0.5752	Remote Similarity	NPD5857	Phase 3
0.5748	Remote Similarity	NPD8104	Phase 3
0.5741	Remote Similarity	NPD8375	Approved
0.5741	Remote Similarity	NPD8291	Clinical (unspecified phase)
0.5741	Remote Similarity	NPD5817	Discontinued
0.5738	Remote Similarity	NPD4900	Clinical (unspecified phase)
0.5736	Remote Similarity	NPD5482	Discontinued
0.5731	Remote Similarity	NPD1927	Discontinued
0.5731	Remote Similarity	NPD5887	Clinical (unspecified phase)
0.5709	Remote Similarity	NPD6790	Phase 1
0.5709	Remote Similarity	NPD7417	Discontinued
0.5709	Remote Similarity	NPD4086	Phase 1
0.5698	Remote Similarity	NPD3074	Discontinued
0.5698	Remote Similarity	NPD8371	Clinical (unspecified phase)
0.5681	Remote Similarity	NPD7796	Approved
0.5681	Remote Similarity	NPD7797	Approved
0.5673	Remote Similarity	NPD1166	Clinical (unspecified phase)
0.567	Remote Similarity	NPD7886	Phase 2
0.567	Remote Similarity	NPD7885	Phase 2
0.5669	Remote Similarity	NPD8289	Discontinued
0.5665	Remote Similarity	NPD4334	Discontinued
0.5664	Remote Similarity	NPD8374	Phase 3
0.565	Remote Similarity	NPD7470	Discontinued
0.565	Remote Similarity	NPD7703	Clinical (unspecified phase)
0.565	Remote Similarity	NPD5416	Discontinued
0.5647	Remote Similarity	NPD5499	Approved
0.5645	Remote Similarity	NPD5417	Clinical (unspecified phase)
0.5642	Remote Similarity	NPD7688	Phase 1
0.5642	Remote Similarity	NPD1505	Phase 2
0.5641	Remote Similarity	NPD5461	Discontinued
0.564	Remote Similarity	NPD5632	Approved
0.5638	Remote Similarity	NPD6231	Phase 3
0.5637	Remote Similarity	NPD8329	Phase 3
0.563	Remote Similarity	NPD8049	Phase 2
0.5628	Remote Similarity	NPD8097	Phase 3
0.5628	Remote Similarity	NPD7605	Discovery
0.5628	Remote Similarity	NPD8096	Phase 3
0.5622	Remote Similarity	NPD6393	Clinical (unspecified phase)
0.5618	Remote Similarity	NPD8459	Approved
0.5618	Remote Similarity	NPD8460	Approved
0.5615	Remote Similarity	NPD8322	Phase 2
0.5613	Remote Similarity	NPD2311	Clinical (unspecified phase)
0.561	Remote Similarity	NPD2081	Clinical (unspecified phase)
0.56	Remote Similarity	NPD8000	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