NPASS Compound

Structure

NPC52931 OpenBabel07101718312D 33 36 0 0 1 0 0 0 0 0999 V2000 6.2813 -0.4781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2377 5.2577 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1037 4.7577 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8912 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8308 1.7790 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.4153 -1.9781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.4035 3.2644 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0676 2.7015 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5493 -2.4781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7377 -0.7737 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9945 2.7226 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6887 -1.0827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5878 1.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1371 2.2872 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1371 0.3309 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.4153 -0.9781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5493 3.0962 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.3450 1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5493 -0.4781 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 6.0416 1.8312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6832 -1.9781 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.7377 3.3917 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.9945 -0.1045 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.6832 3.5962 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2377 4.2577 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6832 -0.9781 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.5878 0.8090 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.8172 -2.4781 0.0000 Br 0 0 0 0 0 0 0 0 0 0 0 0 0.2377 4.2577 0.0000 Br 0 0 0 0 0 0 0 0 0 0 0 0 6.9292 1.3706 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.9923 4.5472 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.6887 3.7007 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 16 2 0 0 0 0 2 25 1 0 0 0 0 3 25 1 0 0 0 0 6 9 1 0 0 0 0 6 16 1 0 0 0 0 7 8 2 0 0 0 0 7 17 1 0 0 0 0 8 20 1 0 0 0 0 9 21 1 0 0 0 0 10 12 1 0 0 0 0 10 23 1 0 0 0 0 11 13 1 0 0 0 0 11 22 1 0 0 0 0 12 26 1 0 0 0 0 13 27 1 0 0 0 0 14 17 2 0 0 0 0 14 18 1 0 0 0 0 15 18 1 0 0 0 0 15 19 1 0 0 0 0 16 19 1 0 0 0 0 17 24 1 0 0 0 0 18 20 2 0 0 0 0 19 26 1 6 0 0 0 20 30 1 0 0 0 0 21 26 1 6 0 0 0 21 28 1 0 0 0 0 22 25 1 1 0 0 0 22 32 1 0 0 0 0 23 27 1 6 0 0 0 23 33 1 0 0 0 0 24 31 2 0 0 0 0 24 32 1 0 0 0 0 25 29 1 0 0 0 0 26 4 1 6 0 0 0 27 5 1 6 0 0 0 27 33 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	582.1
Volume:	501.868
LogP:	6.927
LogD:	4.64
LogS:	-5.822
# Rotatable Bonds:	1
TPSA:	59.06
# H-Bond Aceptor:	4
# H-Bond Donor:	1
# Rings:	4
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.166
Synthetic Accessibility Score:	5.998
Fsp3:	0.667
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	2
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.702
MDCK Permeability:	2.187726386182476e-05
Pgp-inhibitor:	0.996
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.005
20% Bioavailability (F20%):	0.048
30% Bioavailability (F30%):	0.112

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.155
Plasma Protein Binding (PPB):	99.6204605102539%
Volume Distribution (VD):	1.024
Pgp-substrate:	1.8820526599884033%

ADMET: Metabolism

CYP1A2-inhibitor:	0.188
CYP1A2-substrate:	0.165
CYP2C19-inhibitor:	0.717
CYP2C19-substrate:	0.44
CYP2C9-inhibitor:	0.905
CYP2C9-substrate:	0.728
CYP2D6-inhibitor:	0.16
CYP2D6-substrate:	0.883
CYP3A4-inhibitor:	0.817
CYP3A4-substrate:	0.461

ADMET: Excretion

Clearance (CL):	7.624
Half-life (T1/2):	0.062

ADMET: Toxicity

hERG Blockers:	0.168
Human Hepatotoxicity (H-HT):	0.2
Drug-inuced Liver Injury (DILI):	0.772
AMES Toxicity:	0.055
Rat Oral Acute Toxicity:	0.463
Maximum Recommended Daily Dose:	0.9
Skin Sensitization:	0.771
Carcinogencity:	0.415
Eye Corrosion:	0.826
Eye Irritation:	0.701
Respiratory Toxicity:	0.97

Download Data

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

Natural Product: NPC52931

Natural Product ID:	NPC52931
*Common Name:**	Bromophycolide S
IUPAC Name:	n.a.
Synonyms:	Bromophycolide S
Standard InCHIKey:	XXZGDAJOFSALEJ-KXSKSBKOSA-N
Standard InCHI:	InChI=1S/C27H36Br2O4/c1-16-6-9-21(28)26(4)12-10-23-27(5,33-23)13-11-22(25(2,3)29)32-24(31)17-7-8-20(30)18(14-17)15-19(16)26/h7-8,14,19,21-23,30H,1,6,9-13,15H2,2-5H3/t19-,21+,22+,23+,26+,27+/m1/s1
SMILES:	O=C1O[C@@H](CC[C@]2(C)O[C@H]2CC[C@]2([C@H](Cc3cc1ccc3O)C(=C)CC[C@@H]2Br)C)C(Br)(C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1081435
PubChem CID:	46184569
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000147] Macrolides and analogues

*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
NPO8966	Callophycus serratus	Species	Solieriaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16268553]
NPO8966	Callophycus serratus	Species	Solieriaceae	Eukaryota	n.a.	Fijian red alga	n.a.	PMID[16724831]
NPO8966	Callophycus serratus	Species	Solieriaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17715978]
NPO8966	Callophycus serratus	Species	Solieriaceae	Eukaryota	n.a.	Fijian red alga	n.a.	PMID[20141173]
NPO8966	Callophycus serratus	Species	Solieriaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[30407005]
NPO8966	Callophycus serratus	Species	Solieriaceae	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	4
MIC	1

Activity Type	# Activity
Organism	5

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	900.0	nM	PMID[506620]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	IC50	>	15000.0	nM	PMID[506620]
NPT1531	Organism	Enterococcus faecium	Enterococcus faecium	IC50	=	3800.0	nM	PMID[506620]
NPT88	Organism	Mycobacterium tuberculosis	Mycobacterium tuberculosis	MIC	=	23000.0	nM	PMID[506620]
NPT20	Organism	Candida albicans	Candida albicans	IC50	>	15000.0	nM	PMID[506620]

☑ 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 NPC52931 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	342
0.1-0.2	1355
0.2-0.3	2714
0.3-0.4	6681
0.4-0.5	11698
0.5-0.6	6768
0.6-0.7	10799
0.7-0.8	2308
0.8-0.85	23
0.85-0.9	1
0.9-0.95	5
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.993	High Similarity	NPC17600
0.9724	High Similarity	NPC475093
0.9589	High Similarity	NPC11892
0.9577	High Similarity	NPC271451
0.9514	High Similarity	NPC469498
0.9444	High Similarity	NPC97188
0.9257	High Similarity	NPC37642
0.8581	High Similarity	NPC469911
0.8414	Intermediate Similarity	NPC302844
0.8392	Intermediate Similarity	NPC473744
0.838	Intermediate Similarity	NPC204579
0.8345	Intermediate Similarity	NPC473777
0.8312	Intermediate Similarity	NPC66991
0.8301	Intermediate Similarity	NPC208293
0.8264	Intermediate Similarity	NPC229894
0.8252	Intermediate Similarity	NPC110211
0.8247	Intermediate Similarity	NPC286038
0.8239	Intermediate Similarity	NPC184219
0.8217	Intermediate Similarity	NPC48671
0.8207	Intermediate Similarity	NPC117899
0.8205	Intermediate Similarity	NPC179128
0.8205	Intermediate Similarity	NPC162569
0.8205	Intermediate Similarity	NPC87630
0.8205	Intermediate Similarity	NPC116292
0.8205	Intermediate Similarity	NPC35160
0.8205	Intermediate Similarity	NPC267469
0.8194	Intermediate Similarity	NPC325032
0.8194	Intermediate Similarity	NPC477483
0.8182	Intermediate Similarity	NPC75295
0.8182	Intermediate Similarity	NPC258856
0.8153	Intermediate Similarity	NPC140133
0.8141	Intermediate Similarity	NPC279442
0.8138	Intermediate Similarity	NPC193203
0.8133	Intermediate Similarity	NPC477592
0.8099	Intermediate Similarity	NPC67300
0.8095	Intermediate Similarity	NPC18798
0.8092	Intermediate Similarity	NPC172311
0.8089	Intermediate Similarity	NPC247219
0.8089	Intermediate Similarity	NPC327962
0.8079	Intermediate Similarity	NPC477593
0.8056	Intermediate Similarity	NPC137416
0.8056	Intermediate Similarity	NPC49938
0.8054	Intermediate Similarity	NPC477594
0.8042	Intermediate Similarity	NPC174991
0.8039	Intermediate Similarity	NPC184053
0.8039	Intermediate Similarity	NPC477595
0.8013	Intermediate Similarity	NPC170718
0.8	Intermediate Similarity	NPC477596
0.7972	Intermediate Similarity	NPC475192
0.7961	Intermediate Similarity	NPC221104
0.7959	Intermediate Similarity	NPC194979
0.795	Intermediate Similarity	NPC472807
0.7947	Intermediate Similarity	NPC291454
0.7945	Intermediate Similarity	NPC121104
0.7933	Intermediate Similarity	NPC194970
0.7933	Intermediate Similarity	NPC477893
0.7922	Intermediate Similarity	NPC470842
0.7922	Intermediate Similarity	NPC477894
0.7898	Intermediate Similarity	NPC473023
0.7895	Intermediate Similarity	NPC119542
0.7891	Intermediate Similarity	NPC2596
0.7888	Intermediate Similarity	NPC62051
0.7885	Intermediate Similarity	NPC478203
0.7885	Intermediate Similarity	NPC126882
0.7885	Intermediate Similarity	NPC42540
0.7885	Intermediate Similarity	NPC260152
0.7885	Intermediate Similarity	NPC151607
0.7885	Intermediate Similarity	NPC210966
0.7875	Intermediate Similarity	NPC124842
0.7875	Intermediate Similarity	NPC221249
0.7871	Intermediate Similarity	NPC308572
0.7867	Intermediate Similarity	NPC472591
0.7862	Intermediate Similarity	NPC142654
0.7857	Intermediate Similarity	NPC472600
0.7857	Intermediate Similarity	NPC168471
0.7857	Intermediate Similarity	NPC472601
0.7848	Intermediate Similarity	NPC5568
0.7848	Intermediate Similarity	NPC81835
0.7843	Intermediate Similarity	NPC23870
0.784	Intermediate Similarity	NPC159692
0.7834	Intermediate Similarity	NPC83272
0.7834	Intermediate Similarity	NPC257558
0.7829	Intermediate Similarity	NPC475111
0.7821	Intermediate Similarity	NPC159721
0.7815	Intermediate Similarity	NPC477896
0.7808	Intermediate Similarity	NPC275576
0.7806	Intermediate Similarity	NPC472603
0.7806	Intermediate Similarity	NPC472605
0.7806	Intermediate Similarity	NPC472604
0.78	Intermediate Similarity	NPC165612
0.7799	Intermediate Similarity	NPC473719
0.7792	Intermediate Similarity	NPC88269
0.7785	Intermediate Similarity	NPC109778
0.7785	Intermediate Similarity	NPC327457
0.7785	Intermediate Similarity	NPC86774
0.7785	Intermediate Similarity	NPC51513
0.7785	Intermediate Similarity	NPC202112
0.7778	Intermediate Similarity	NPC301915
0.7778	Intermediate Similarity	NPC71256
0.7778	Intermediate Similarity	NPC24394
0.7778	Intermediate Similarity	NPC261292
0.7778	Intermediate Similarity	NPC194579
0.7778	Intermediate Similarity	NPC70380
0.7763	Intermediate Similarity	NPC477874
0.7763	Intermediate Similarity	NPC173569
0.7763	Intermediate Similarity	NPC27407
0.7763	Intermediate Similarity	NPC142027
0.7755	Intermediate Similarity	NPC169913
0.775	Intermediate Similarity	NPC120171
0.7748	Intermediate Similarity	NPC239855
0.7748	Intermediate Similarity	NPC49742
0.7746	Intermediate Similarity	NPC94298
0.7746	Intermediate Similarity	NPC474890
0.7746	Intermediate Similarity	NPC161943
0.7746	Intermediate Similarity	NPC27633
0.7746	Intermediate Similarity	NPC273282
0.7742	Intermediate Similarity	NPC327916
0.7742	Intermediate Similarity	NPC37992
0.7742	Intermediate Similarity	NPC241349
0.7742	Intermediate Similarity	NPC51181
0.7742	Intermediate Similarity	NPC147542
0.7742	Intermediate Similarity	NPC32749
0.7742	Intermediate Similarity	NPC470986
0.7742	Intermediate Similarity	NPC42262
0.7742	Intermediate Similarity	NPC220496
0.774	Intermediate Similarity	NPC10154
0.774	Intermediate Similarity	NPC265413
0.7736	Intermediate Similarity	NPC119767
0.7733	Intermediate Similarity	NPC238370
0.7727	Intermediate Similarity	NPC191835
0.7727	Intermediate Similarity	NPC212693
0.7727	Intermediate Similarity	NPC478200
0.7727	Intermediate Similarity	NPC472602
0.7727	Intermediate Similarity	NPC94248
0.7727	Intermediate Similarity	NPC33144
0.7725	Intermediate Similarity	NPC161151
0.7725	Intermediate Similarity	NPC471687
0.7722	Intermediate Similarity	NPC84786
0.7712	Intermediate Similarity	NPC249817
0.7711	Intermediate Similarity	NPC477627
0.7708	Intermediate Similarity	NPC164852
0.7707	Intermediate Similarity	NPC469615
0.7707	Intermediate Similarity	NPC472610
0.7707	Intermediate Similarity	NPC476473
0.7707	Intermediate Similarity	NPC100242
0.7707	Intermediate Similarity	NPC471731
0.7707	Intermediate Similarity	NPC478202
0.7702	Intermediate Similarity	NPC56204
0.7697	Intermediate Similarity	NPC204582
0.7697	Intermediate Similarity	NPC239118
0.7697	Intermediate Similarity	NPC202225
0.7692	Intermediate Similarity	NPC471444
0.7692	Intermediate Similarity	NPC478201
0.7692	Intermediate Similarity	NPC158634
0.7692	Intermediate Similarity	NPC53649
0.7692	Intermediate Similarity	NPC313123
0.7692	Intermediate Similarity	NPC478217
0.7692	Intermediate Similarity	NPC257003
0.7692	Intermediate Similarity	NPC11056
0.7692	Intermediate Similarity	NPC472035
0.7688	Intermediate Similarity	NPC94781
0.7688	Intermediate Similarity	NPC161955
0.7682	Intermediate Similarity	NPC476389
0.7677	Intermediate Similarity	NPC216312
0.7677	Intermediate Similarity	NPC114620
0.7677	Intermediate Similarity	NPC476477
0.7677	Intermediate Similarity	NPC112789
0.7677	Intermediate Similarity	NPC473988
0.7677	Intermediate Similarity	NPC256463
0.7677	Intermediate Similarity	NPC103337
0.7677	Intermediate Similarity	NPC29771
0.7677	Intermediate Similarity	NPC471602
0.7677	Intermediate Similarity	NPC306835
0.7677	Intermediate Similarity	NPC19622
0.7677	Intermediate Similarity	NPC299405
0.7677	Intermediate Similarity	NPC111422
0.7673	Intermediate Similarity	NPC191899
0.7673	Intermediate Similarity	NPC246229
0.7673	Intermediate Similarity	NPC25844
0.7673	Intermediate Similarity	NPC147250
0.7673	Intermediate Similarity	NPC107625
0.7673	Intermediate Similarity	NPC474991
0.7667	Intermediate Similarity	NPC245395
0.7665	Intermediate Similarity	NPC473022
0.7662	Intermediate Similarity	NPC216940
0.7662	Intermediate Similarity	NPC198621
0.7662	Intermediate Similarity	NPC22676
0.7662	Intermediate Similarity	NPC475482
0.7658	Intermediate Similarity	NPC469683
0.7658	Intermediate Similarity	NPC169942
0.7658	Intermediate Similarity	NPC71739
0.7658	Intermediate Similarity	NPC471305
0.7654	Intermediate Similarity	NPC473131
0.7654	Intermediate Similarity	NPC470675
0.7651	Intermediate Similarity	NPC2401
0.7651	Intermediate Similarity	NPC3009
0.7647	Intermediate Similarity	NPC279463
0.7647	Intermediate Similarity	NPC472372
0.7647	Intermediate Similarity	NPC472374
0.7643	Intermediate Similarity	NPC474300

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 NPC52931 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	294
0.1-0.2	901
0.2-0.3	1576
0.3-0.4	2669
0.4-0.5	2168
0.5-0.6	1127
0.6-0.7	397
0.7-0.8	18
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
0.7806	Intermediate Similarity	NPD4628	Phase 3
0.7746	Intermediate Similarity	NPD9545	Approved
0.7742	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7667	Intermediate Similarity	NPD3764	Approved
0.7531	Intermediate Similarity	NPD7458	Discontinued
0.7468	Intermediate Similarity	NPD7003	Approved
0.7455	Intermediate Similarity	NPD7819	Suspended
0.7436	Intermediate Similarity	NPD2935	Discontinued
0.7425	Intermediate Similarity	NPD7075	Discontinued
0.7372	Intermediate Similarity	NPD2799	Discontinued
0.7349	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7342	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7305	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7284	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7284	Intermediate Similarity	NPD2533	Approved
0.7284	Intermediate Similarity	NPD2534	Approved
0.7284	Intermediate Similarity	NPD2532	Approved
0.7273	Intermediate Similarity	NPD4380	Phase 2
0.7262	Intermediate Similarity	NPD7768	Phase 2
0.725	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.725	Intermediate Similarity	NPD3750	Approved
0.725	Intermediate Similarity	NPD8166	Discontinued
0.7229	Intermediate Similarity	NPD7411	Suspended
0.7211	Intermediate Similarity	NPD4196	Clinical (unspecified phase)
0.7208	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7202	Intermediate Similarity	NPD4288	Approved
0.7179	Intermediate Similarity	NPD230	Phase 1
0.7169	Intermediate Similarity	NPD6599	Discontinued
0.7161	Intermediate Similarity	NPD6663	Approved
0.716	Intermediate Similarity	NPD7236	Approved
0.7152	Intermediate Similarity	NPD1510	Phase 2
0.7143	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD5844	Phase 1
0.7134	Intermediate Similarity	NPD6273	Approved
0.7126	Intermediate Similarity	NPD7473	Discontinued
0.7125	Intermediate Similarity	NPD1549	Phase 2
0.7124	Intermediate Similarity	NPD5736	Approved
0.7115	Intermediate Similarity	NPD1240	Approved
0.7108	Intermediate Similarity	NPD3226	Approved
0.7083	Intermediate Similarity	NPD6801	Discontinued
0.7073	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7073	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.707	Intermediate Similarity	NPD6355	Discontinued
0.7069	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7063	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7063	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7063	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD6007	Clinical (unspecified phase)
0.7052	Intermediate Similarity	NPD6232	Discontinued
0.7032	Intermediate Similarity	NPD5952	Clinical (unspecified phase)
0.7025	Intermediate Similarity	NPD1607	Approved
0.7025	Intermediate Similarity	NPD6651	Approved
0.702	Intermediate Similarity	NPD1608	Approved
0.702	Intermediate Similarity	NPD3972	Approved
0.7017	Intermediate Similarity	NPD8150	Discontinued
0.7012	Intermediate Similarity	NPD6799	Approved
0.7007	Intermediate Similarity	NPD9493	Approved
0.7006	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD6099	Approved
0.7	Intermediate Similarity	NPD5408	Approved
0.7	Intermediate Similarity	NPD5405	Approved
0.7	Intermediate Similarity	NPD2796	Approved
0.7	Intermediate Similarity	NPD5404	Approved
0.7	Intermediate Similarity	NPD6100	Approved
0.7	Intermediate Similarity	NPD5406	Approved
0.6994	Remote Similarity	NPD6190	Approved
0.6993	Remote Similarity	NPD1164	Approved
0.6987	Remote Similarity	NPD2313	Discontinued
0.6975	Remote Similarity	NPD2800	Approved
0.6972	Remote Similarity	NPD9265	Clinical (unspecified phase)
0.6957	Remote Similarity	NPD6002	Phase 3
0.6957	Remote Similarity	NPD6005	Phase 3
0.6957	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.6957	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.6957	Remote Similarity	NPD6004	Phase 3
0.6957	Remote Similarity	NPD2346	Discontinued
0.6946	Remote Similarity	NPD7239	Suspended
0.6937	Remote Similarity	NPD3748	Approved
0.6937	Remote Similarity	NPD7033	Discontinued
0.6928	Remote Similarity	NPD1283	Approved
0.6927	Remote Similarity	NPD7685	Pre-registration
0.6923	Remote Similarity	NPD6831	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD8434	Phase 2
0.6923	Remote Similarity	NPD7615	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD7008	Discontinued
0.6919	Remote Similarity	NPD3749	Approved
0.6919	Remote Similarity	NPD4381	Clinical (unspecified phase)
0.6901	Remote Similarity	NPD2296	Approved
0.6899	Remote Similarity	NPD4060	Phase 1
0.6899	Remote Similarity	NPD2979	Phase 3
0.6897	Remote Similarity	NPD8127	Discontinued
0.6897	Remote Similarity	NPD6959	Discontinued
0.6894	Remote Similarity	NPD4476	Approved
0.6894	Remote Similarity	NPD4477	Approved
0.6894	Remote Similarity	NPD1551	Phase 2
0.6883	Remote Similarity	NPD2797	Approved
0.6882	Remote Similarity	NPD1934	Approved
0.6879	Remote Similarity	NPD3268	Approved
0.6868	Remote Similarity	NPD8055	Clinical (unspecified phase)
0.6865	Remote Similarity	NPD7879	Clinical (unspecified phase)
0.6859	Remote Similarity	NPD6832	Phase 2
0.6854	Remote Similarity	NPD7286	Phase 2
0.6854	Remote Similarity	NPD7804	Clinical (unspecified phase)
0.6852	Remote Similarity	NPD2344	Approved
0.6848	Remote Similarity	NPD8397	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD5760	Phase 2
0.6842	Remote Similarity	NPD5761	Phase 2
0.6839	Remote Similarity	NPD2798	Approved
0.6832	Remote Similarity	NPD4308	Phase 3
0.6832	Remote Similarity	NPD1509	Clinical (unspecified phase)
0.6829	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.6821	Remote Similarity	NPD17	Approved
0.6821	Remote Similarity	NPD4626	Approved
0.6807	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6798	Remote Similarity	NPD7177	Discontinued
0.6786	Remote Similarity	NPD920	Approved
0.6778	Remote Similarity	NPD5953	Discontinued
0.6774	Remote Similarity	NPD1203	Approved
0.6774	Remote Similarity	NPD1470	Approved
0.6772	Remote Similarity	NPD6798	Discontinued
0.6761	Remote Similarity	NPD5711	Approved
0.6761	Remote Similarity	NPD7229	Phase 3
0.6761	Remote Similarity	NPD5710	Approved
0.6758	Remote Similarity	NPD8312	Approved
0.6758	Remote Similarity	NPD8313	Approved
0.6757	Remote Similarity	NPD5951	Approved
0.6757	Remote Similarity	NPD4287	Approved
0.6755	Remote Similarity	NPD5691	Approved
0.675	Remote Similarity	NPD5123	Clinical (unspecified phase)
0.675	Remote Similarity	NPD5124	Phase 1
0.6744	Remote Similarity	NPD8455	Phase 2
0.6743	Remote Similarity	NPD5494	Approved
0.6732	Remote Similarity	NPD1281	Approved
0.6732	Remote Similarity	NPD1201	Approved
0.673	Remote Similarity	NPD4870	Approved
0.6726	Remote Similarity	NPD7314	Clinical (unspecified phase)
0.6712	Remote Similarity	NPD2181	Clinical (unspecified phase)
0.6711	Remote Similarity	NPD1778	Approved
0.6711	Remote Similarity	NPD2932	Approved
0.6711	Remote Similarity	NPD3019	Approved
0.6711	Remote Similarity	NPD3412	Clinical (unspecified phase)
0.671	Remote Similarity	NPD1876	Approved
0.6707	Remote Similarity	NPD7390	Discontinued
0.6705	Remote Similarity	NPD3817	Phase 2
0.6704	Remote Similarity	NPD7893	Clinical (unspecified phase)
0.669	Remote Similarity	NPD2182	Approved
0.6688	Remote Similarity	NPD9717	Approved
0.6687	Remote Similarity	NPD2309	Approved
0.6687	Remote Similarity	NPD2438	Suspended
0.6687	Remote Similarity	NPD3887	Approved
0.6667	Remote Similarity	NPD3882	Suspended
0.6667	Remote Similarity	NPD4907	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD7097	Phase 1
0.6667	Remote Similarity	NPD642	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD1243	Approved
0.6667	Remote Similarity	NPD7422	Clinical (unspecified phase)
0.6648	Remote Similarity	NPD6559	Discontinued
0.6648	Remote Similarity	NPD6765	Approved
0.6648	Remote Similarity	NPD6764	Approved
0.6647	Remote Similarity	NPD6666	Approved
0.6647	Remote Similarity	NPD1465	Phase 2
0.6647	Remote Similarity	NPD6667	Approved
0.6647	Remote Similarity	NPD643	Clinical (unspecified phase)
0.6647	Remote Similarity	NPD7440	Discontinued
0.6647	Remote Similarity	NPD2801	Approved
0.6646	Remote Similarity	NPD7266	Discontinued
0.6645	Remote Similarity	NPD5585	Approved
0.6644	Remote Similarity	NPD2629	Approved
0.663	Remote Similarity	NPD7074	Phase 3
0.6628	Remote Similarity	NPD6385	Approved
0.6628	Remote Similarity	NPD6386	Approved
0.6627	Remote Similarity	NPD4110	Phase 3
0.6627	Remote Similarity	NPD5049	Phase 3
0.6627	Remote Similarity	NPD4109	Clinical (unspecified phase)
0.6627	Remote Similarity	NPD3400	Discontinued
0.6625	Remote Similarity	NPD8032	Phase 2
0.6611	Remote Similarity	NPD3818	Discontinued
0.6611	Remote Similarity	NPD7799	Discontinued
0.6608	Remote Similarity	NPD3455	Phase 2
0.6607	Remote Similarity	NPD1511	Approved
0.6604	Remote Similarity	NPD7095	Approved
0.6593	Remote Similarity	NPD7993	Clinical (unspecified phase)
0.6592	Remote Similarity	NPD6166	Phase 2
0.6592	Remote Similarity	NPD3451	Clinical (unspecified phase)
0.6592	Remote Similarity	NPD6168	Clinical (unspecified phase)
0.6592	Remote Similarity	NPD6167	Clinical (unspecified phase)
0.6591	Remote Similarity	NPD6234	Discontinued
0.659	Remote Similarity	NPD37	Approved
0.6588	Remote Similarity	NPD5403	Approved
0.6587	Remote Similarity	NPD2354	Approved
0.6585	Remote Similarity	NPD2531	Phase 2
0.6584	Remote Similarity	NPD943	Approved
0.6584	Remote Similarity	NPD4140	Approved
0.6584	Remote Similarity	NPD4307	Phase 2
0.6582	Remote Similarity	NPD2861	Phase 2
0.6581	Remote Similarity	NPD1481	Phase 2
0.6579	Remote Similarity	NPD7741	Discontinued
0.6575	Remote Similarity	NPD7054	Approved
0.6571	Remote Similarity	NPD4967	Phase 2

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