NPASS Compound

Structure

NPC475093 OpenBabel07101719142D 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 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 0.2377 4.2577 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 29 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 30 2 0 0 0 0 24 32 1 0 0 0 0 25 31 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:	520.18
Volume:	491.375
LogP:	5.836
LogD:	4.035
LogS:	-4.312
# Rotatable Bonds:	1
TPSA:	79.29
# H-Bond Aceptor:	5
# H-Bond Donor:	2
# Rings:	4
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.215
Synthetic Accessibility Score:	5.881
Fsp3:	0.667
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:	-4.618
MDCK Permeability:	2.293528632435482e-05
Pgp-inhibitor:	0.992
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.003
20% Bioavailability (F20%):	0.016
30% Bioavailability (F30%):	0.07

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.187
Plasma Protein Binding (PPB):	97.2736587524414%
Volume Distribution (VD):	0.894
Pgp-substrate:	2.042030096054077%

ADMET: Metabolism

CYP1A2-inhibitor:	0.084
CYP1A2-substrate:	0.191
CYP2C19-inhibitor:	0.228
CYP2C19-substrate:	0.333
CYP2C9-inhibitor:	0.791
CYP2C9-substrate:	0.578
CYP2D6-inhibitor:	0.068
CYP2D6-substrate:	0.759
CYP3A4-inhibitor:	0.795
CYP3A4-substrate:	0.319

ADMET: Excretion

Clearance (CL):	10.265
Half-life (T1/2):	0.221

ADMET: Toxicity

hERG Blockers:	0.141
Human Hepatotoxicity (H-HT):	0.268
Drug-inuced Liver Injury (DILI):	0.515
AMES Toxicity:	0.058
Rat Oral Acute Toxicity:	0.348
Maximum Recommended Daily Dose:	0.885
Skin Sensitization:	0.66
Carcinogencity:	0.453
Eye Corrosion:	0.026
Eye Irritation:	0.073
Respiratory Toxicity:	0.962

Download Data

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

Natural Product: NPC475093

Natural Product ID:	NPC475093
*Common Name:**	Bromophycolide F
IUPAC Name:	n.a.
Synonyms:	Bromophycolide F
Standard InCHIKey:	DRPSOKQUGMQRLO-KXSKSBKOSA-N
Standard InCHI:	InChI=1S/C27H37BrO5/c1-16-6-9-21(28)26(4)12-10-23-27(5,33-23)13-11-22(25(2,3)31)32-24(30)17-7-8-20(29)18(14-17)15-19(16)26/h7-8,14,19,21-23,29,31H,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(O)(C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL497244
PubChem CID:	11511959
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	1

Activity Type	# Activity
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT20	Organism	Candida albicans	Candida albicans	IC50	=	240000.0	nM	PMID[522397]

☑ 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 NPC475093 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	349
0.1-0.2	1300
0.2-0.3	2744
0.3-0.4	6390
0.4-0.5	11330
0.5-0.6	6707
0.6-0.7	10827
0.7-0.8	3027
0.8-0.85	14
0.85-0.9	2
0.9-0.95	3
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
0.9792	High Similarity	NPC17600
0.9726	High Similarity	NPC11892
0.9724	High Similarity	NPC52931
0.931	High Similarity	NPC271451
0.9262	High Similarity	NPC37642
0.9252	High Similarity	NPC469498
0.9184	High Similarity	NPC97188
0.8844	High Similarity	NPC469911
0.8681	High Similarity	NPC302844
0.8483	Intermediate Similarity	NPC473777
0.8312	Intermediate Similarity	NPC258856
0.8312	Intermediate Similarity	NPC75295
0.8289	Intermediate Similarity	NPC184053
0.8276	Intermediate Similarity	NPC473744
0.8264	Intermediate Similarity	NPC204579
0.8217	Intermediate Similarity	NPC327962
0.8205	Intermediate Similarity	NPC66991
0.8194	Intermediate Similarity	NPC208293
0.8151	Intermediate Similarity	NPC229894
0.8141	Intermediate Similarity	NPC286038
0.8138	Intermediate Similarity	NPC110211
0.8125	Intermediate Similarity	NPC184219
0.8125	Intermediate Similarity	NPC62051
0.8113	Intermediate Similarity	NPC48671
0.8113	Intermediate Similarity	NPC124842
0.8101	Intermediate Similarity	NPC116292
0.8101	Intermediate Similarity	NPC162569
0.8101	Intermediate Similarity	NPC267469
0.8101	Intermediate Similarity	NPC35160
0.8101	Intermediate Similarity	NPC87630
0.8101	Intermediate Similarity	NPC179128
0.8095	Intermediate Similarity	NPC117899
0.8089	Intermediate Similarity	NPC477483
0.8089	Intermediate Similarity	NPC325032
0.8089	Intermediate Similarity	NPC81835
0.8075	Intermediate Similarity	NPC472807
0.8067	Intermediate Similarity	NPC477896
0.8067	Intermediate Similarity	NPC477893
0.8052	Intermediate Similarity	NPC477894
0.805	Intermediate Similarity	NPC140133
0.8038	Intermediate Similarity	NPC279442
0.8027	Intermediate Similarity	NPC193203
0.8026	Intermediate Similarity	NPC477592
0.8025	Intermediate Similarity	NPC473023
0.8	Intermediate Similarity	NPC221249
0.7987	Intermediate Similarity	NPC247219
0.7987	Intermediate Similarity	NPC172311
0.7987	Intermediate Similarity	NPC18798
0.7987	Intermediate Similarity	NPC142654
0.7986	Intermediate Similarity	NPC67300
0.7974	Intermediate Similarity	NPC477593
0.7962	Intermediate Similarity	NPC83272
0.7961	Intermediate Similarity	NPC475111
0.7949	Intermediate Similarity	NPC469615
0.7947	Intermediate Similarity	NPC477594
0.7945	Intermediate Similarity	NPC49938
0.7945	Intermediate Similarity	NPC137416
0.7939	Intermediate Similarity	NPC477627
0.7935	Intermediate Similarity	NPC477595
0.7931	Intermediate Similarity	NPC174991
0.7925	Intermediate Similarity	NPC94781
0.7925	Intermediate Similarity	NPC161955
0.7911	Intermediate Similarity	NPC191899
0.7911	Intermediate Similarity	NPC246229
0.7908	Intermediate Similarity	NPC170718
0.7898	Intermediate Similarity	NPC469683
0.7895	Intermediate Similarity	NPC477596
0.7881	Intermediate Similarity	NPC239855
0.7875	Intermediate Similarity	NPC120171
0.7871	Intermediate Similarity	NPC3218
0.7871	Intermediate Similarity	NPC64664
0.7862	Intermediate Similarity	NPC127046
0.7862	Intermediate Similarity	NPC475192
0.7862	Intermediate Similarity	NPC14875
0.7857	Intermediate Similarity	NPC149002
0.7857	Intermediate Similarity	NPC88176
0.7857	Intermediate Similarity	NPC469396
0.7857	Intermediate Similarity	NPC469419
0.7857	Intermediate Similarity	NPC469459
0.7857	Intermediate Similarity	NPC221104
0.7857	Intermediate Similarity	NPC469458
0.7852	Intermediate Similarity	NPC194979
0.7848	Intermediate Similarity	NPC84786
0.7844	Intermediate Similarity	NPC161151
0.7843	Intermediate Similarity	NPC291454
0.7838	Intermediate Similarity	NPC121104
0.7834	Intermediate Similarity	NPC25491
0.7831	Intermediate Similarity	NPC293568
0.7831	Intermediate Similarity	NPC117943
0.7831	Intermediate Similarity	NPC92589
0.7829	Intermediate Similarity	NPC204582
0.7829	Intermediate Similarity	NPC194970
0.7826	Intermediate Similarity	NPC56204
0.7821	Intermediate Similarity	NPC470842
0.7821	Intermediate Similarity	NPC2681
0.7821	Intermediate Similarity	NPC130485
0.7821	Intermediate Similarity	NPC272907
0.7799	Intermediate Similarity	NPC474991
0.7799	Intermediate Similarity	NPC470330
0.7799	Intermediate Similarity	NPC316769
0.7792	Intermediate Similarity	NPC119542
0.7785	Intermediate Similarity	NPC126882
0.7785	Intermediate Similarity	NPC2596
0.7785	Intermediate Similarity	NPC210966
0.7785	Intermediate Similarity	NPC260152
0.7785	Intermediate Similarity	NPC151607
0.7785	Intermediate Similarity	NPC42540
0.7785	Intermediate Similarity	NPC478203
0.7778	Intermediate Similarity	NPC472372
0.7778	Intermediate Similarity	NPC472374
0.7778	Intermediate Similarity	NPC472551
0.7778	Intermediate Similarity	NPC472545
0.7778	Intermediate Similarity	NPC205918
0.7771	Intermediate Similarity	NPC478250
0.7771	Intermediate Similarity	NPC308572
0.7764	Intermediate Similarity	NPC280753
0.7764	Intermediate Similarity	NPC474305
0.7764	Intermediate Similarity	NPC478219
0.7764	Intermediate Similarity	NPC44378
0.7763	Intermediate Similarity	NPC114116
0.7763	Intermediate Similarity	NPC19719
0.7763	Intermediate Similarity	NPC477280
0.7763	Intermediate Similarity	NPC477281
0.7763	Intermediate Similarity	NPC472591
0.7756	Intermediate Similarity	NPC472601
0.7756	Intermediate Similarity	NPC168471
0.7756	Intermediate Similarity	NPC27518
0.7756	Intermediate Similarity	NPC192658
0.7756	Intermediate Similarity	NPC304110
0.7756	Intermediate Similarity	NPC158472
0.7756	Intermediate Similarity	NPC472600
0.7751	Intermediate Similarity	NPC200726
0.775	Intermediate Similarity	NPC5568
0.7744	Intermediate Similarity	NPC472890
0.7744	Intermediate Similarity	NPC159692
0.7742	Intermediate Similarity	NPC275592
0.7742	Intermediate Similarity	NPC171207
0.7742	Intermediate Similarity	NPC472547
0.7742	Intermediate Similarity	NPC197666
0.7742	Intermediate Similarity	NPC97667
0.7742	Intermediate Similarity	NPC100913
0.7742	Intermediate Similarity	NPC23870
0.7742	Intermediate Similarity	NPC126739
0.7738	Intermediate Similarity	NPC100420
0.7736	Intermediate Similarity	NPC257558
0.773	Intermediate Similarity	NPC115249
0.773	Intermediate Similarity	NPC184284
0.773	Intermediate Similarity	NPC256141
0.773	Intermediate Similarity	NPC229354
0.773	Intermediate Similarity	NPC76041
0.773	Intermediate Similarity	NPC131121
0.773	Intermediate Similarity	NPC257847
0.7727	Intermediate Similarity	NPC39549
0.7725	Intermediate Similarity	NPC266365
0.7725	Intermediate Similarity	NPC469889
0.7722	Intermediate Similarity	NPC159721
0.7722	Intermediate Similarity	NPC127857
0.7719	Intermediate Similarity	NPC472803
0.7716	Intermediate Similarity	NPC289021
0.7716	Intermediate Similarity	NPC469619
0.7716	Intermediate Similarity	NPC469670
0.7716	Intermediate Similarity	NPC158546
0.7716	Intermediate Similarity	NPC180351
0.7716	Intermediate Similarity	NPC472421
0.7716	Intermediate Similarity	NPC119252
0.7712	Intermediate Similarity	NPC311339
0.7711	Intermediate Similarity	NPC470339
0.7707	Intermediate Similarity	NPC472605
0.7707	Intermediate Similarity	NPC95449
0.7707	Intermediate Similarity	NPC472603
0.7707	Intermediate Similarity	NPC472604
0.7706	Intermediate Similarity	NPC177362
0.7703	Intermediate Similarity	NPC275576
0.7702	Intermediate Similarity	NPC475848
0.7702	Intermediate Similarity	NPC473719
0.7702	Intermediate Similarity	NPC474306
0.7697	Intermediate Similarity	NPC109967
0.7697	Intermediate Similarity	NPC475797
0.7697	Intermediate Similarity	NPC321372
0.7697	Intermediate Similarity	NPC88007
0.7697	Intermediate Similarity	NPC129053
0.7697	Intermediate Similarity	NPC78554
0.7697	Intermediate Similarity	NPC474609
0.7697	Intermediate Similarity	NPC471787
0.7697	Intermediate Similarity	NPC194499
0.7697	Intermediate Similarity	NPC471968
0.7697	Intermediate Similarity	NPC478223
0.7697	Intermediate Similarity	NPC327204
0.7697	Intermediate Similarity	NPC469936
0.7697	Intermediate Similarity	NPC165612
0.7697	Intermediate Similarity	NPC474738
0.7697	Intermediate Similarity	NPC7059
0.7697	Intermediate Similarity	NPC323379
0.7692	Intermediate Similarity	NPC41481
0.7692	Intermediate Similarity	NPC472576
0.7692	Intermediate Similarity	NPC27377
0.7692	Intermediate Similarity	NPC118080
0.7692	Intermediate Similarity	NPC211592
0.7692	Intermediate Similarity	NPC291599
0.7692	Intermediate Similarity	NPC88269

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 NPC475093 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	300
0.1-0.2	853
0.2-0.3	1633
0.3-0.4	2685
0.4-0.5	2137
0.5-0.6	1087
0.6-0.7	433
0.7-0.8	22
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
0.8052	Intermediate Similarity	NPD4628	Phase 3
0.7654	Intermediate Similarity	NPD7458	Discontinued
0.7651	Intermediate Similarity	NPD7075	Discontinued
0.7643	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7639	Intermediate Similarity	NPD9545	Approved
0.7576	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7566	Intermediate Similarity	NPD3764	Approved
0.75	Intermediate Similarity	NPD4380	Phase 2
0.7394	Intermediate Similarity	NPD6599	Discontinued
0.7375	Intermediate Similarity	NPD7003	Approved
0.7375	Intermediate Similarity	NPD8166	Discontinued
0.7365	Intermediate Similarity	NPD7819	Suspended
0.7342	Intermediate Similarity	NPD2935	Discontinued
0.7308	Intermediate Similarity	NPD230	Phase 1
0.7308	Intermediate Similarity	NPD6355	Discontinued
0.7305	Intermediate Similarity	NPD6801	Discontinued
0.7278	Intermediate Similarity	NPD2799	Discontinued
0.7278	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7262	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7257	Intermediate Similarity	NPD5844	Phase 1
0.725	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7241	Intermediate Similarity	NPD7473	Discontinued
0.7239	Intermediate Similarity	NPD6799	Approved
0.7222	Intermediate Similarity	NPD6190	Approved
0.7222	Intermediate Similarity	NPD8150	Discontinued
0.7219	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7195	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7195	Intermediate Similarity	NPD2532	Approved
0.7195	Intermediate Similarity	NPD2534	Approved
0.7195	Intermediate Similarity	NPD2533	Approved
0.7176	Intermediate Similarity	NPD7768	Phase 2
0.7168	Intermediate Similarity	NPD6232	Discontinued
0.7161	Intermediate Similarity	NPD5952	Clinical (unspecified phase)
0.716	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.716	Intermediate Similarity	NPD3750	Approved
0.7143	Intermediate Similarity	NPD7411	Suspended
0.7135	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7135	Intermediate Similarity	NPD7685	Pre-registration
0.7134	Intermediate Similarity	NPD4060	Phase 1
0.7127	Intermediate Similarity	NPD8434	Phase 2
0.7115	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7114	Intermediate Similarity	NPD4196	Clinical (unspecified phase)
0.7101	Intermediate Similarity	NPD1934	Approved
0.7073	Intermediate Similarity	NPD7236	Approved
0.7072	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.707	Intermediate Similarity	NPD6663	Approved
0.7065	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7063	Intermediate Similarity	NPD1510	Phase 2
0.7062	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7049	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7048	Intermediate Similarity	NPD6273	Approved
0.7037	Intermediate Similarity	NPD1549	Phase 2
0.7032	Intermediate Similarity	NPD5736	Approved
0.7025	Intermediate Similarity	NPD1240	Approved
0.7024	Intermediate Similarity	NPD3226	Approved
0.7018	Intermediate Similarity	NPD4288	Approved
0.7011	Intermediate Similarity	NPD8127	Discontinued
0.7006	Intermediate Similarity	NPD6798	Discontinued
0.6989	Remote Similarity	NPD7852	Clinical (unspecified phase)
0.6988	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6988	Remote Similarity	NPD7410	Clinical (unspecified phase)
0.6975	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.6975	Remote Similarity	NPD2343	Clinical (unspecified phase)
0.6975	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6968	Remote Similarity	NPD6007	Clinical (unspecified phase)
0.6961	Remote Similarity	NPD8312	Approved
0.6961	Remote Similarity	NPD8313	Approved
0.6959	Remote Similarity	NPD8455	Phase 2
0.6937	Remote Similarity	NPD6651	Approved
0.6937	Remote Similarity	NPD1607	Approved
0.6928	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6928	Remote Similarity	NPD3972	Approved
0.6928	Remote Similarity	NPD1608	Approved
0.6923	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6919	Remote Similarity	NPD3817	Phase 2
0.6914	Remote Similarity	NPD5406	Approved
0.6914	Remote Similarity	NPD6100	Approved
0.6914	Remote Similarity	NPD5408	Approved
0.6914	Remote Similarity	NPD5405	Approved
0.6914	Remote Similarity	NPD6099	Approved
0.6914	Remote Similarity	NPD2796	Approved
0.6914	Remote Similarity	NPD5404	Approved
0.6913	Remote Similarity	NPD9493	Approved
0.6903	Remote Similarity	NPD1164	Approved
0.6899	Remote Similarity	NPD2313	Discontinued
0.6892	Remote Similarity	NPD2629	Approved
0.689	Remote Similarity	NPD2800	Approved
0.6879	Remote Similarity	NPD3882	Suspended
0.6875	Remote Similarity	NPD9265	Clinical (unspecified phase)
0.6871	Remote Similarity	NPD7266	Discontinued
0.6871	Remote Similarity	NPD2346	Discontinued
0.6871	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.6871	Remote Similarity	NPD6004	Phase 3
0.6871	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.6871	Remote Similarity	NPD6005	Phase 3
0.6871	Remote Similarity	NPD6002	Phase 3
0.6864	Remote Similarity	NPD7239	Suspended
0.686	Remote Similarity	NPD2801	Approved
0.686	Remote Similarity	NPD1465	Phase 2
0.6857	Remote Similarity	NPD5494	Approved
0.6852	Remote Similarity	NPD3748	Approved
0.6852	Remote Similarity	NPD7033	Discontinued
0.6851	Remote Similarity	NPD6559	Discontinued
0.6845	Remote Similarity	NPD7314	Clinical (unspecified phase)
0.6845	Remote Similarity	NPD5049	Phase 3
0.6842	Remote Similarity	NPD7615	Clinical (unspecified phase)
0.6839	Remote Similarity	NPD1283	Approved
0.6839	Remote Similarity	NPD3749	Approved
0.6835	Remote Similarity	NPD7008	Discontinued
0.6835	Remote Similarity	NPD7095	Approved
0.6833	Remote Similarity	NPD7074	Phase 3
0.6828	Remote Similarity	NPD6831	Clinical (unspecified phase)
0.6824	Remote Similarity	NPD3455	Phase 2
0.6818	Remote Similarity	NPD6959	Discontinued
0.6816	Remote Similarity	NPD3818	Discontinued
0.6813	Remote Similarity	NPD2979	Phase 3
0.681	Remote Similarity	NPD4476	Approved
0.681	Remote Similarity	NPD2438	Suspended
0.681	Remote Similarity	NPD1551	Phase 2
0.681	Remote Similarity	NPD4477	Approved
0.6807	Remote Similarity	NPD3887	Approved
0.6807	Remote Similarity	NPD2354	Approved
0.6805	Remote Similarity	NPD5403	Approved
0.68	Remote Similarity	NPD6234	Discontinued
0.6798	Remote Similarity	NPD6166	Phase 2
0.6798	Remote Similarity	NPD6168	Clinical (unspecified phase)
0.6798	Remote Similarity	NPD6167	Clinical (unspecified phase)
0.6796	Remote Similarity	NPD7993	Clinical (unspecified phase)
0.6795	Remote Similarity	NPD2797	Approved
0.6792	Remote Similarity	NPD3268	Approved
0.679	Remote Similarity	NPD7097	Phase 1
0.6786	Remote Similarity	NPD7422	Clinical (unspecified phase)
0.6778	Remote Similarity	NPD7286	Phase 2
0.6778	Remote Similarity	NPD7054	Approved
0.6772	Remote Similarity	NPD6832	Phase 2
0.6768	Remote Similarity	NPD5763	Approved
0.6768	Remote Similarity	NPD5762	Approved
0.6768	Remote Similarity	NPD2344	Approved
0.6763	Remote Similarity	NPD5760	Phase 2
0.6763	Remote Similarity	NPD5761	Phase 2
0.6758	Remote Similarity	NPD6764	Approved
0.6758	Remote Similarity	NPD6765	Approved
0.6753	Remote Similarity	NPD8319	Approved
0.6753	Remote Similarity	NPD8320	Phase 1
0.6752	Remote Similarity	NPD2798	Approved
0.675	Remote Similarity	NPD6233	Phase 2
0.6748	Remote Similarity	NPD1509	Clinical (unspecified phase)
0.6748	Remote Similarity	NPD4308	Phase 3
0.6747	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.6747	Remote Similarity	NPD4110	Phase 3
0.6747	Remote Similarity	NPD4109	Clinical (unspecified phase)
0.6744	Remote Similarity	NPD6386	Approved
0.6744	Remote Similarity	NPD6385	Approved
0.674	Remote Similarity	NPD7472	Approved
0.6732	Remote Similarity	NPD17	Approved
0.6732	Remote Similarity	NPD4626	Approved
0.6731	Remote Similarity	NPD8651	Approved
0.6727	Remote Similarity	NPD4534	Discontinued
0.6726	Remote Similarity	NPD1511	Approved
0.6724	Remote Similarity	NPD5402	Approved
0.6724	Remote Similarity	NPD2296	Approved
0.6722	Remote Similarity	NPD7177	Discontinued
0.6722	Remote Similarity	NPD7799	Discontinued
0.6709	Remote Similarity	NPD9494	Approved
0.6708	Remote Similarity	NPD943	Approved
0.6706	Remote Similarity	NPD920	Approved
0.6705	Remote Similarity	NPD37	Approved
0.6703	Remote Similarity	NPD5953	Discontinued
0.6701	Remote Similarity	NPD7497	Discontinued
0.6701	Remote Similarity	NPD7435	Discontinued
0.6688	Remote Similarity	NPD1470	Approved
0.6688	Remote Similarity	NPD1203	Approved
0.6686	Remote Similarity	NPD4965	Approved
0.6686	Remote Similarity	NPD5401	Approved
0.6686	Remote Similarity	NPD4966	Approved
0.6686	Remote Similarity	NPD4967	Phase 2
0.6685	Remote Similarity	NPD5711	Approved
0.6685	Remote Similarity	NPD5710	Approved
0.6685	Remote Similarity	NPD7229	Phase 3
0.6667	Remote Similarity	NPD6652	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD5691	Approved
0.6667	Remote Similarity	NPD8368	Discontinued
0.6667	Remote Similarity	NPD5123	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD7251	Discontinued
0.6667	Remote Similarity	NPD5124	Phase 1
0.6667	Remote Similarity	NPD5951	Approved
0.6647	Remote Similarity	NPD1512	Approved
0.6647	Remote Similarity	NPD6873	Phase 2
0.6646	Remote Similarity	NPD4062	Phase 3
0.6645	Remote Similarity	NPD1201	Approved
0.6645	Remote Similarity	NPD1281	Approved
0.6632	Remote Similarity	NPD6534	Approved
0.6632	Remote Similarity	NPD6535	Approved
0.663	Remote Similarity	NPD7228	Approved
0.663	Remote Similarity	NPD4338	Clinical (unspecified phase)
0.663	Remote Similarity	NPD3751	Discontinued
0.663	Remote Similarity	NPD7808	Phase 3
0.663	Remote Similarity	NPD7893	Clinical (unspecified phase)
0.6629	Remote Similarity	NPD7199	Phase 2
0.6627	Remote Similarity	NPD2424	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