NPASS Compound

Structure

NPC329626 OpenBabel07101718292D 23 25 0 0 1 0 0 0 0 0999 V2000 1.5388 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2709 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4049 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1756 1.6180 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5000 -1.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2709 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2709 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9511 -0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5878 -0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4049 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4049 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5878 0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4049 -1.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.9511 0.3090 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.5878 0.8090 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.5388 0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.5388 -0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.5878 -0.8090 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.0000 -1.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.9021 0.6180 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.5000 -1.8660 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 11 1 0 0 0 0 2 11 1 0 0 0 0 3 12 2 0 0 0 0 4 13 2 0 0 0 0 5 20 1 0 0 0 0 6 7 1 0 0 0 0 6 12 1 0 0 0 0 7 14 1 0 0 0 0 8 9 1 0 0 0 0 8 15 1 0 0 0 0 9 20 1 0 0 0 0 10 13 1 0 0 0 0 13 15 1 0 0 0 0 14 11 1 6 0 0 0 14 18 1 0 0 0 0 15 21 1 6 0 0 0 16 10 1 1 0 0 0 16 17 1 0 0 0 0 16 23 1 0 0 0 0 17 12 1 1 0 0 0 17 18 1 0 0 0 0 18 19 1 0 0 0 0 19 20 1 0 0 0 0 19 23 1 0 0 0 0 20 22 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	320.24
Volume:	349.905
LogP:	3.349
LogD:	3.657
LogS:	-3.938
# Rotatable Bonds:	1
TPSA:	49.69
# H-Bond Aceptor:	3
# H-Bond Donor:	2
# Rings:	3
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.728
Synthetic Accessibility Score:	5.937
Fsp3:	0.8
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
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:	-4.561
MDCK Permeability:	1.1961075870203786e-05
Pgp-inhibitor:	0.001
Pgp-substrate:	0.201
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.266
30% Bioavailability (F30%):	0.029

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.45
Plasma Protein Binding (PPB):	57.16522216796875%
Volume Distribution (VD):	0.752
Pgp-substrate:	38.21257781982422%

ADMET: Metabolism

CYP1A2-inhibitor:	0.04
CYP1A2-substrate:	0.164
CYP2C19-inhibitor:	0.014
CYP2C19-substrate:	0.801
CYP2C9-inhibitor:	0.023
CYP2C9-substrate:	0.056
CYP2D6-inhibitor:	0.003
CYP2D6-substrate:	0.131
CYP3A4-inhibitor:	0.095
CYP3A4-substrate:	0.379

ADMET: Excretion

Clearance (CL):	12.228
Half-life (T1/2):	0.295

ADMET: Toxicity

hERG Blockers:	0.042
Human Hepatotoxicity (H-HT):	0.257
Drug-inuced Liver Injury (DILI):	0.241
AMES Toxicity:	0.012
Rat Oral Acute Toxicity:	0.61
Maximum Recommended Daily Dose:	0.886
Skin Sensitization:	0.052
Carcinogencity:	0.455
Eye Corrosion:	0.035
Eye Irritation:	0.067
Respiratory Toxicity:	0.955

Download Data

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

Natural Product: NPC329626

Natural Product ID:	NPC329626
*Common Name:**	Cladiellisin
IUPAC Name:	n.a.
Synonyms:	Cladiellisin
Standard InCHIKey:	KIZAKRQUJAYYGA-SCDLFQHWSA-N
Standard InCHI:	InChI=1S/C20H32O3/c1-11(2)14-7-6-12(3)17-16-10-13(4)15(21)8-9-20(5,22)19(23-16)18(14)17/h11,14-19,21-22H,3-4,6-10H2,1-2,5H3/t14-,15+,16+,17-,18-,19+,20+/m1/s1
SMILES:	C=C1CC[C@@H]([C@@H]2[C@H]1[C@@H]1CC(=C)[C@@H](O)CC[C@]([C@H]2O1)(C)O)C(C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL464225
PubChem CID:	44567169
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001551] Diterpenoids [CHEMONTID:0002916] Eunicellane and asbestinane 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
NPO3452	Virgularia juncea	Species	Virgulariidae	Eukaryota	n.a.	n.a.	n.a.	PMID[11575967]
NPO22114	Cladiella pachyclados	Species	Alcyoniidae	Eukaryota	n.a.	red sea soft coral	n.a.	PMID[20420415]
NPO3452	Virgularia juncea	Species	Virgulariidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22114	Cladiella pachyclados	Species	Alcyoniidae	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
ED50	1
IC50	2

Activity Type	# Activity
Cell Line	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT168	Cell Line	P388	Mus musculus	ED50	=	2.0	ug ml-1	PMID[558477]
NPT306	Cell Line	PC-3	Homo sapiens	IC50	=	88000.0	nM	PMID[558480]
NPT306	Cell Line	PC-3	Homo sapiens	IC50	=	11363627.79	nM	PMID[558480]

☑ 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 NPC329626 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	160
0.1-0.2	1796
0.2-0.3	7173
0.3-0.4	15979
0.4-0.5	7893
0.5-0.6	7927
0.6-0.7	1685
0.7-0.8	57
0.8-0.85	13
0.85-0.9	9
0.9-0.95	4
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9444	High Similarity	NPC293223
0.9306	High Similarity	NPC36479
0.9079	High Similarity	NPC77003
0.8861	High Similarity	NPC196911
0.8861	High Similarity	NPC471379
0.8846	High Similarity	NPC5958
0.8831	High Similarity	NPC118116
0.8718	High Similarity	NPC103171
0.8608	High Similarity	NPC239308
0.8533	High Similarity	NPC12696
0.8519	High Similarity	NPC321812
0.8519	High Similarity	NPC475684
0.8519	High Similarity	NPC322922
0.8415	Intermediate Similarity	NPC44538
0.8333	Intermediate Similarity	NPC471378
0.8333	Intermediate Similarity	NPC312471
0.8313	Intermediate Similarity	NPC92370
0.8313	Intermediate Similarity	NPC476723
0.8313	Intermediate Similarity	NPC476724
0.8313	Intermediate Similarity	NPC470260
0.8313	Intermediate Similarity	NPC75443
0.8228	Intermediate Similarity	NPC76054
0.8214	Intermediate Similarity	NPC161560
0.8214	Intermediate Similarity	NPC291875
0.8205	Intermediate Similarity	NPC264610
0.8023	Intermediate Similarity	NPC208839
0.8023	Intermediate Similarity	NPC122057
0.8023	Intermediate Similarity	NPC91251
0.7882	Intermediate Similarity	NPC309656
0.7875	Intermediate Similarity	NPC72755
0.7875	Intermediate Similarity	NPC476367
0.7848	Intermediate Similarity	NPC476703
0.7816	Intermediate Similarity	NPC312805
0.7808	Intermediate Similarity	NPC250836
0.7792	Intermediate Similarity	NPC476709
0.7738	Intermediate Similarity	NPC476725
0.7711	Intermediate Similarity	NPC127917
0.7654	Intermediate Similarity	NPC476701
0.7647	Intermediate Similarity	NPC476217
0.7586	Intermediate Similarity	NPC115607
0.7564	Intermediate Similarity	NPC143576
0.7558	Intermediate Similarity	NPC476948
0.7531	Intermediate Similarity	NPC477089
0.7531	Intermediate Similarity	NPC52755
0.7529	Intermediate Similarity	NPC290731
0.75	Intermediate Similarity	NPC256720
0.75	Intermediate Similarity	NPC236228
0.7471	Intermediate Similarity	NPC473436
0.7416	Intermediate Similarity	NPC8729
0.7412	Intermediate Similarity	NPC83702
0.7403	Intermediate Similarity	NPC16964
0.7403	Intermediate Similarity	NPC234511
0.7386	Intermediate Similarity	NPC97103
0.7363	Intermediate Similarity	NPC476720
0.7349	Intermediate Similarity	NPC474592
0.7342	Intermediate Similarity	NPC95165
0.7333	Intermediate Similarity	NPC119379
0.7326	Intermediate Similarity	NPC298595
0.7303	Intermediate Similarity	NPC191323
0.7294	Intermediate Similarity	NPC477978
0.7284	Intermediate Similarity	NPC136424
0.7284	Intermediate Similarity	NPC170148
0.7283	Intermediate Similarity	NPC210717
0.7283	Intermediate Similarity	NPC103165
0.7273	Intermediate Similarity	NPC22376
0.7273	Intermediate Similarity	NPC245795
0.7273	Intermediate Similarity	NPC266578
0.7273	Intermediate Similarity	NPC305698
0.7262	Intermediate Similarity	NPC5361
0.7253	Intermediate Similarity	NPC473258
0.725	Intermediate Similarity	NPC190859
0.7237	Intermediate Similarity	NPC476406
0.7234	Intermediate Similarity	NPC272223
0.7229	Intermediate Similarity	NPC233295
0.7222	Intermediate Similarity	NPC471747
0.7222	Intermediate Similarity	NPC114389
0.7222	Intermediate Similarity	NPC302584
0.7216	Intermediate Similarity	NPC470263
0.7215	Intermediate Similarity	NPC306085
0.7209	Intermediate Similarity	NPC151176
0.7209	Intermediate Similarity	NPC3464
0.7209	Intermediate Similarity	NPC475963
0.7204	Intermediate Similarity	NPC261807
0.7204	Intermediate Similarity	NPC26307
0.7204	Intermediate Similarity	NPC111348
0.7195	Intermediate Similarity	NPC477427
0.7195	Intermediate Similarity	NPC477426
0.7195	Intermediate Similarity	NPC474826
0.7195	Intermediate Similarity	NPC477425
0.7191	Intermediate Similarity	NPC477917
0.7179	Intermediate Similarity	NPC304690
0.7179	Intermediate Similarity	NPC9942
0.7179	Intermediate Similarity	NPC74722
0.7159	Intermediate Similarity	NPC251808
0.7159	Intermediate Similarity	NPC474174
0.7159	Intermediate Similarity	NPC189777
0.7143	Intermediate Similarity	NPC259299
0.7143	Intermediate Similarity	NPC47149
0.7143	Intermediate Similarity	NPC137461
0.7126	Intermediate Similarity	NPC119001
0.7111	Intermediate Similarity	NPC159876
0.7111	Intermediate Similarity	NPC470832
0.7108	Intermediate Similarity	NPC137345
0.7108	Intermediate Similarity	NPC475
0.7108	Intermediate Similarity	NPC181838
0.7108	Intermediate Similarity	NPC252483
0.7108	Intermediate Similarity	NPC3852
0.7108	Intermediate Similarity	NPC191345
0.7108	Intermediate Similarity	NPC43463
0.7108	Intermediate Similarity	NPC472502
0.7105	Intermediate Similarity	NPC471200
0.7097	Intermediate Similarity	NPC8803
0.7093	Intermediate Similarity	NPC320548
0.7093	Intermediate Similarity	NPC260852
0.7089	Intermediate Similarity	NPC283316
0.7079	Intermediate Similarity	NPC474668
0.7073	Intermediate Similarity	NPC476606
0.7073	Intermediate Similarity	NPC470766
0.7067	Intermediate Similarity	NPC50435
0.7051	Intermediate Similarity	NPC276616
0.7045	Intermediate Similarity	NPC255143
0.7045	Intermediate Similarity	NPC214315
0.7037	Intermediate Similarity	NPC306727
0.7033	Intermediate Similarity	NPC210268
0.7024	Intermediate Similarity	NPC24504
0.7021	Intermediate Similarity	NPC473244
0.7013	Intermediate Similarity	NPC267027
0.7013	Intermediate Similarity	NPC311736
0.7011	Intermediate Similarity	NPC242016
0.7011	Intermediate Similarity	NPC86238
0.7011	Intermediate Similarity	NPC319238
0.7011	Intermediate Similarity	NPC102048
0.7011	Intermediate Similarity	NPC474780
0.7	Intermediate Similarity	NPC128066
0.7	Intermediate Similarity	NPC470361
0.7	Intermediate Similarity	NPC473058
0.6989	Remote Similarity	NPC86893
0.6989	Remote Similarity	NPC473348
0.6989	Remote Similarity	NPC292178
0.6989	Remote Similarity	NPC30477
0.6989	Remote Similarity	NPC8774
0.6988	Remote Similarity	NPC40049
0.6988	Remote Similarity	NPC130136
0.6988	Remote Similarity	NPC476719
0.6988	Remote Similarity	NPC31037
0.6977	Remote Similarity	NPC477390
0.6977	Remote Similarity	NPC477385
0.6977	Remote Similarity	NPC155521
0.6974	Remote Similarity	NPC476702
0.6966	Remote Similarity	NPC233744
0.6962	Remote Similarity	NPC472947
0.6957	Remote Similarity	NPC474792
0.6957	Remote Similarity	NPC91654
0.6957	Remote Similarity	NPC296620
0.6957	Remote Similarity	NPC67398
0.6957	Remote Similarity	NPC98193
0.6957	Remote Similarity	NPC474835
0.6951	Remote Similarity	NPC472950
0.6951	Remote Similarity	NPC32832
0.6951	Remote Similarity	NPC472952
0.6951	Remote Similarity	NPC476605
0.6947	Remote Similarity	NPC476895
0.6944	Remote Similarity	NPC24443
0.6941	Remote Similarity	NPC96362
0.6941	Remote Similarity	NPC287749
0.6941	Remote Similarity	NPC324772
0.6932	Remote Similarity	NPC164424
0.6923	Remote Similarity	NPC73603
0.6923	Remote Similarity	NPC163290
0.6923	Remote Similarity	NPC291484
0.6923	Remote Similarity	NPC82337
0.6923	Remote Similarity	NPC206614
0.6923	Remote Similarity	NPC474323
0.6923	Remote Similarity	NPC11216
0.6923	Remote Similarity	NPC470817
0.6923	Remote Similarity	NPC329596
0.6923	Remote Similarity	NPC3345
0.6923	Remote Similarity	NPC161612
0.6923	Remote Similarity	NPC33583
0.6923	Remote Similarity	NPC269077
0.6923	Remote Similarity	NPC253303
0.6923	Remote Similarity	NPC204188
0.6923	Remote Similarity	NPC80561
0.6915	Remote Similarity	NPC98457
0.6915	Remote Similarity	NPC90583
0.6915	Remote Similarity	NPC292718
0.6915	Remote Similarity	NPC72204
0.6915	Remote Similarity	NPC12103
0.6915	Remote Similarity	NPC111834
0.6915	Remote Similarity	NPC227583
0.6915	Remote Similarity	NPC288970
0.6915	Remote Similarity	NPC169270
0.6915	Remote Similarity	NPC306797
0.6914	Remote Similarity	NPC472506
0.6905	Remote Similarity	NPC167891
0.6905	Remote Similarity	NPC301707
0.6905	Remote Similarity	NPC472500
0.6905	Remote Similarity	NPC68119
0.6905	Remote Similarity	NPC137587
0.6905	Remote Similarity	NPC472499

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 NPC329626 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	161
0.1-0.2	2466
0.2-0.3	4133
0.3-0.4	1666
0.4-0.5	446
0.5-0.6	244
0.6-0.7	32
0.7-0.8	2
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
0.7356	Intermediate Similarity	NPD7524	Approved
0.7209	Intermediate Similarity	NPD7338	Clinical (unspecified phase)
0.7093	Intermediate Similarity	NPD6695	Phase 3
0.6941	Remote Similarity	NPD6931	Approved
0.6941	Remote Similarity	NPD6930	Phase 2
0.6867	Remote Similarity	NPD6933	Approved
0.6824	Remote Similarity	NPD6929	Approved
0.6778	Remote Similarity	NPD7750	Discontinued
0.6633	Remote Similarity	NPD5344	Discontinued
0.6627	Remote Similarity	NPD6926	Approved
0.6627	Remote Similarity	NPD6924	Approved
0.6588	Remote Similarity	NPD5776	Phase 2
0.6588	Remote Similarity	NPD6925	Approved
0.6579	Remote Similarity	NPD1145	Discontinued
0.6556	Remote Similarity	NPD6893	Approved
0.6552	Remote Similarity	NPD7332	Phase 2
0.6552	Remote Similarity	NPD7514	Phase 3
0.6512	Remote Similarity	NPD7145	Approved
0.6489	Remote Similarity	NPD7087	Discontinued
0.6477	Remote Similarity	NPD6898	Phase 1
0.6413	Remote Similarity	NPD4751	Clinical (unspecified phase)
0.6395	Remote Similarity	NPD6932	Approved
0.6364	Remote Similarity	NPD7525	Registered
0.6364	Remote Similarity	NPD7509	Discontinued
0.6353	Remote Similarity	NPD6942	Approved
0.6353	Remote Similarity	NPD7339	Approved
0.6329	Remote Similarity	NPD371	Approved
0.6322	Remote Similarity	NPD7322	Clinical (unspecified phase)
0.6292	Remote Similarity	NPD6902	Approved
0.6282	Remote Similarity	NPD368	Approved
0.6279	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.6263	Remote Similarity	NPD4225	Approved
0.625	Remote Similarity	NPD6683	Phase 2
0.6211	Remote Similarity	NPD6698	Approved
0.6211	Remote Similarity	NPD46	Approved
0.6211	Remote Similarity	NPD7838	Discovery
0.6211	Remote Similarity	NPD3168	Discontinued
0.62	Remote Similarity	NPD6648	Approved
0.6163	Remote Similarity	NPD8264	Approved
0.6146	Remote Similarity	NPD7983	Approved
0.6145	Remote Similarity	NPD6923	Approved
0.6145	Remote Similarity	NPD6922	Approved
0.6095	Remote Similarity	NPD6686	Approved
0.6071	Remote Similarity	NPD7144	Approved
0.6071	Remote Similarity	NPD7143	Approved
0.6067	Remote Similarity	NPD7645	Phase 2
0.6064	Remote Similarity	NPD4251	Approved
0.6064	Remote Similarity	NPD4250	Approved
0.604	Remote Similarity	NPD7639	Approved
0.604	Remote Similarity	NPD7640	Approved
0.6	Remote Similarity	NPD7150	Approved
0.6	Remote Similarity	NPD6412	Phase 2
0.6	Remote Similarity	NPD7152	Approved
0.6	Remote Similarity	NPD7151	Approved
0.5979	Remote Similarity	NPD7637	Suspended
0.5963	Remote Similarity	NPD8133	Approved
0.5957	Remote Similarity	NPD4249	Approved
0.5941	Remote Similarity	NPD7638	Approved
0.5941	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.5926	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.5918	Remote Similarity	NPD5778	Approved
0.5918	Remote Similarity	NPD5779	Approved
0.5914	Remote Similarity	NPD4786	Approved
0.5905	Remote Similarity	NPD6640	Phase 3
0.5882	Remote Similarity	NPD7532	Clinical (unspecified phase)
0.587	Remote Similarity	NPD3667	Approved
0.5862	Remote Similarity	NPD1811	Approved
0.5862	Remote Similarity	NPD1810	Approved
0.5862	Remote Similarity	NPD4785	Approved
0.5862	Remote Similarity	NPD4784	Approved
0.5859	Remote Similarity	NPD5282	Discontinued
0.5849	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.5833	Remote Similarity	NPD6371	Approved
0.5824	Remote Similarity	NPD6928	Phase 2
0.5824	Remote Similarity	NPD4819	Approved
0.5824	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.5824	Remote Similarity	NPD4821	Approved
0.5824	Remote Similarity	NPD4820	Approved
0.5824	Remote Similarity	NPD4748	Discontinued
0.5824	Remote Similarity	NPD4822	Approved
0.5814	Remote Similarity	NPD4243	Approved
0.5806	Remote Similarity	NPD4788	Approved
0.5806	Remote Similarity	NPD6110	Phase 1
0.5794	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.5765	Remote Similarity	NPD4267	Clinical (unspecified phase)
0.5758	Remote Similarity	NPD6399	Phase 3
0.5755	Remote Similarity	NPD5357	Phase 1
0.5752	Remote Similarity	NPD7327	Approved
0.5752	Remote Similarity	NPD7328	Approved
0.5747	Remote Similarity	NPD4732	Discontinued
0.5743	Remote Similarity	NPD4792	Clinical (unspecified phase)
0.5741	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.5739	Remote Similarity	NPD8033	Approved
0.5714	Remote Similarity	NPD342	Phase 1
0.5714	Remote Similarity	NPD7136	Phase 2
0.5702	Remote Similarity	NPD7516	Approved
0.5684	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.5673	Remote Similarity	NPD4159	Approved
0.5657	Remote Similarity	NPD8034	Phase 2
0.5657	Remote Similarity	NPD8035	Phase 2
0.5652	Remote Similarity	NPD8377	Approved
0.5652	Remote Similarity	NPD8294	Approved
0.5638	Remote Similarity	NPD5362	Discontinued
0.5638	Remote Similarity	NPD7154	Phase 3
0.5619	Remote Similarity	NPD3653	Clinical (unspecified phase)
0.5619	Remote Similarity	NPD7632	Discontinued
0.5604	Remote Similarity	NPD4268	Approved
0.5604	Remote Similarity	NPD4271	Approved
0.5603	Remote Similarity	NPD8378	Approved
0.5603	Remote Similarity	NPD8380	Approved
0.5603	Remote Similarity	NPD8296	Approved
0.5603	Remote Similarity	NPD8379	Approved
0.5603	Remote Similarity	NPD7503	Approved
0.5603	Remote Similarity	NPD8335	Approved
0.56	Remote Similarity	NPD8171	Discontinued

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