NPASS Compound

Structure

NPC271451 OpenBabel07101718322D 34 36 0 0 1 0 0 0 0 0999 V2000 5.3597 0.5603 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1034 -0.2573 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2932 -1.2112 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0549 -0.5886 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9450 -4.5609 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.2020 -0.8986 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6101 0.2112 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2885 -0.2994 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.2020 -1.8712 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4575 -3.4575 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -2.7697 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1452 -2.7697 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6877 -3.4575 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5589 1.0599 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1452 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.3597 -0.4123 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5863 1.0599 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4575 0.6877 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5174 -0.8986 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.1107 -0.0873 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3722 -1.8712 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 5.3597 -2.3575 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.5589 -3.8296 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.6877 0.6877 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3722 -0.8986 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5174 -1.8712 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.5863 -3.8296 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.3261 -2.0609 0.0000 Br 0 0 0 0 0 0 0 0 0 0 0 0 5.3597 -3.3301 0.0000 Br 0 0 0 0 0 0 0 0 0 0 0 0 2.7486 -4.7836 0.0000 Br 0 0 0 0 0 0 0 0 0 0 0 0 3.7381 -0.8304 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.1474 1.4964 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.8989 -4.7506 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 22 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 21 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 31 1 0 0 0 0 21 25 1 0 0 0 0 21 28 1 1 0 0 0 22 26 1 6 0 0 0 22 29 1 0 0 0 0 23 27 1 1 0 0 0 23 30 1 0 0 0 0 24 32 2 0 0 0 0 24 34 1 0 0 0 0 25 34 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:	662.02
Volume:	529.708
LogP:	7.104
LogD:	4.679
LogS:	-4.49
# Rotatable Bonds:	0
TPSA:	66.76
# H-Bond Aceptor:	4
# H-Bond Donor:	2
# Rings:	3
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.172
Synthetic Accessibility Score:	6.029
Fsp3:	0.667
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Rejected
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:	-4.847
MDCK Permeability:	1.8296226699021645e-05
Pgp-inhibitor:	0.989
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.191
20% Bioavailability (F20%):	0.797
30% Bioavailability (F30%):	0.881

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.068
Plasma Protein Binding (PPB):	100.46923828125%
Volume Distribution (VD):	0.741
Pgp-substrate:	1.935860514640808%

ADMET: Metabolism

CYP1A2-inhibitor:	0.673
CYP1A2-substrate:	0.334
CYP2C19-inhibitor:	0.855
CYP2C19-substrate:	0.513
CYP2C9-inhibitor:	0.972
CYP2C9-substrate:	0.877
CYP2D6-inhibitor:	0.276
CYP2D6-substrate:	0.771
CYP3A4-inhibitor:	0.784
CYP3A4-substrate:	0.854

ADMET: Excretion

Clearance (CL):	4.447
Half-life (T1/2):	0.102

ADMET: Toxicity

hERG Blockers:	0.048
Human Hepatotoxicity (H-HT):	0.635
Drug-inuced Liver Injury (DILI):	0.355
AMES Toxicity:	0.084
Rat Oral Acute Toxicity:	0.374
Maximum Recommended Daily Dose:	0.891
Skin Sensitization:	0.526
Carcinogencity:	0.417
Eye Corrosion:	0.631
Eye Irritation:	0.357
Respiratory Toxicity:	0.966

Download Data

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

Natural Product: NPC271451

Natural Product ID:	NPC271451
*Common Name:**	Bromophycolide H
IUPAC Name:	n.a.
Synonyms:	Bromophycolide H
Standard InCHIKey:	REIKJJVRPXQDAV-UVFQQSMRSA-N
Standard InCHI:	InChI=1S/C27H37Br3O4/c1-16-6-9-22(29)26(4)12-10-23(30)27(5,33)13-11-21(28)25(2,3)34-24(32)17-7-8-20(31)18(14-17)15-19(16)26/h7-8,14,19,21-23,31,33H,1,6,9-13,15H2,2-5H3/t19-,21-,22+,23-,26+,27+/m1/s1
SMILES:	C=C1CC[C@@H]([C@@]2(C)CC[C@H]([C@](C)(CC[C@H](C(C)(C)OC(=O)c3ccc(c(c3)C[C@H]12)O)Br)O)Br)Br
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL524991
PubChem CID:	11578353
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
Cell Line	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1900	Cell Line	DU-4475	Homo sapiens	IC50	=	3880.0	nM	PMID[492198]

☑ 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 NPC271451 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	338
0.1-0.2	1475
0.2-0.3	2860
0.3-0.4	7307
0.4-0.5	11682
0.5-0.6	5872
0.6-0.7	10527
0.7-0.8	2596
0.8-0.85	27
0.85-0.9	6
0.9-0.95	6
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9577	High Similarity	NPC52931
0.9507	High Similarity	NPC17600
0.9444	High Similarity	NPC11892
0.931	High Similarity	NPC475093
0.9296	High Similarity	NPC97188
0.9231	High Similarity	NPC469498
0.911	High Similarity	NPC37642
0.8623	High Similarity	NPC229894
0.8561	High Similarity	NPC117899
0.8489	Intermediate Similarity	NPC193203
0.844	Intermediate Similarity	NPC18798
0.8394	Intermediate Similarity	NPC174991
0.8392	Intermediate Similarity	NPC477594
0.838	Intermediate Similarity	NPC302844
0.8345	Intermediate Similarity	NPC204579
0.8333	Intermediate Similarity	NPC477596
0.8333	Intermediate Similarity	NPC184219
0.8321	Intermediate Similarity	NPC67300
0.8278	Intermediate Similarity	NPC66991
0.8267	Intermediate Similarity	NPC258856
0.8267	Intermediate Similarity	NPC75295
0.8227	Intermediate Similarity	NPC473744
0.8219	Intermediate Similarity	NPC477592
0.8214	Intermediate Similarity	NPC110211
0.8212	Intermediate Similarity	NPC286038
0.8182	Intermediate Similarity	NPC473777
0.8176	Intermediate Similarity	NPC469911
0.8163	Intermediate Similarity	NPC477593
0.8158	Intermediate Similarity	NPC325032
0.8158	Intermediate Similarity	NPC477483
0.8156	Intermediate Similarity	NPC121104
0.8146	Intermediate Similarity	NPC208293
0.8143	Intermediate Similarity	NPC137416
0.8121	Intermediate Similarity	NPC477595
0.8117	Intermediate Similarity	NPC140133
0.8112	Intermediate Similarity	NPC109778
0.8112	Intermediate Similarity	NPC327457
0.8112	Intermediate Similarity	NPC86774
0.8105	Intermediate Similarity	NPC279442
0.8088	Intermediate Similarity	NPC474890
0.8088	Intermediate Similarity	NPC161943
0.8088	Intermediate Similarity	NPC273282
0.8079	Intermediate Similarity	NPC260152
0.8065	Intermediate Similarity	NPC48671
0.8054	Intermediate Similarity	NPC470986
0.8054	Intermediate Similarity	NPC172311
0.8054	Intermediate Similarity	NPC168471
0.8052	Intermediate Similarity	NPC87630
0.8052	Intermediate Similarity	NPC247219
0.8052	Intermediate Similarity	NPC327962
0.8052	Intermediate Similarity	NPC116292
0.8052	Intermediate Similarity	NPC162569
0.8052	Intermediate Similarity	NPC179128
0.8052	Intermediate Similarity	NPC267469
0.8052	Intermediate Similarity	NPC35160
0.8042	Intermediate Similarity	NPC194979
0.8041	Intermediate Similarity	NPC23870
0.8014	Intermediate Similarity	NPC49938
0.7987	Intermediate Similarity	NPC473988
0.7973	Intermediate Similarity	NPC170718
0.7973	Intermediate Similarity	NPC24394
0.7973	Intermediate Similarity	NPC194579
0.7972	Intermediate Similarity	NPC2596
0.7972	Intermediate Similarity	NPC2401
0.7958	Intermediate Similarity	NPC473751
0.7949	Intermediate Similarity	NPC124842
0.7941	Intermediate Similarity	NPC83718
0.7935	Intermediate Similarity	NPC142654
0.7919	Intermediate Similarity	NPC221104
0.7914	Intermediate Similarity	NPC164852
0.7911	Intermediate Similarity	NPC472807
0.7905	Intermediate Similarity	NPC291454
0.7901	Intermediate Similarity	NPC471687
0.7891	Intermediate Similarity	NPC194970
0.7891	Intermediate Similarity	NPC470984
0.7881	Intermediate Similarity	NPC184053
0.7881	Intermediate Similarity	NPC11056
0.7881	Intermediate Similarity	NPC470842
0.7857	Intermediate Similarity	NPC473023
0.7857	Intermediate Similarity	NPC25844
0.7852	Intermediate Similarity	NPC119542
0.7848	Intermediate Similarity	NPC62051
0.7843	Intermediate Similarity	NPC42540
0.7843	Intermediate Similarity	NPC151607
0.7834	Intermediate Similarity	NPC221249
0.7834	Intermediate Similarity	NPC305965
0.7826	Intermediate Similarity	NPC94298
0.7826	Intermediate Similarity	NPC27633
0.7823	Intermediate Similarity	NPC239855
0.7823	Intermediate Similarity	NPC470988
0.7823	Intermediate Similarity	NPC472591
0.7823	Intermediate Similarity	NPC49742
0.7817	Intermediate Similarity	NPC265413
0.7817	Intermediate Similarity	NPC10154
0.7815	Intermediate Similarity	NPC472600
0.7815	Intermediate Similarity	NPC472601
0.781	Intermediate Similarity	NPC131192
0.7806	Intermediate Similarity	NPC125801
0.7806	Intermediate Similarity	NPC5568
0.7801	Intermediate Similarity	NPC475192
0.78	Intermediate Similarity	NPC62735
0.7792	Intermediate Similarity	NPC117716
0.7792	Intermediate Similarity	NPC470673
0.7792	Intermediate Similarity	NPC470674
0.7785	Intermediate Similarity	NPC50455
0.7785	Intermediate Similarity	NPC474726
0.7785	Intermediate Similarity	NPC475955
0.7778	Intermediate Similarity	NPC37512
0.7778	Intermediate Similarity	NPC84672
0.7778	Intermediate Similarity	NPC100242
0.7778	Intermediate Similarity	NPC176130
0.7778	Intermediate Similarity	NPC72667
0.7778	Intermediate Similarity	NPC78364
0.7778	Intermediate Similarity	NPC159721
0.7778	Intermediate Similarity	NPC69424
0.7771	Intermediate Similarity	NPC158866
0.777	Intermediate Similarity	NPC27643
0.777	Intermediate Similarity	NPC477893
0.777	Intermediate Similarity	NPC213122
0.7763	Intermediate Similarity	NPC472605
0.7763	Intermediate Similarity	NPC477272
0.7763	Intermediate Similarity	NPC472603
0.7763	Intermediate Similarity	NPC472604
0.7756	Intermediate Similarity	NPC37139
0.7755	Intermediate Similarity	NPC165612
0.7755	Intermediate Similarity	NPC185624
0.775	Intermediate Similarity	NPC4547
0.775	Intermediate Similarity	NPC471968
0.7748	Intermediate Similarity	NPC19622
0.7748	Intermediate Similarity	NPC21350
0.7748	Intermediate Similarity	NPC88269
0.7748	Intermediate Similarity	NPC112789
0.7742	Intermediate Similarity	NPC154217
0.7742	Intermediate Similarity	NPC181388
0.7742	Intermediate Similarity	NPC477955
0.7742	Intermediate Similarity	NPC225173
0.7742	Intermediate Similarity	NPC163846
0.774	Intermediate Similarity	NPC245395
0.774	Intermediate Similarity	NPC108129
0.7733	Intermediate Similarity	NPC470989
0.7733	Intermediate Similarity	NPC70380
0.7733	Intermediate Similarity	NPC470985
0.7733	Intermediate Similarity	NPC301915
0.7733	Intermediate Similarity	NPC71256
0.7733	Intermediate Similarity	NPC261292
0.7727	Intermediate Similarity	NPC71739
0.7727	Intermediate Similarity	NPC11700
0.7727	Intermediate Similarity	NPC471305
0.7727	Intermediate Similarity	NPC169942
0.7724	Intermediate Similarity	NPC3009
0.7718	Intermediate Similarity	NPC27407
0.7718	Intermediate Similarity	NPC142027
0.7718	Intermediate Similarity	NPC173569
0.7718	Intermediate Similarity	NPC477874
0.7712	Intermediate Similarity	NPC250755
0.7708	Intermediate Similarity	NPC254492
0.7707	Intermediate Similarity	NPC469932
0.7697	Intermediate Similarity	NPC472366
0.7697	Intermediate Similarity	NPC275903
0.7697	Intermediate Similarity	NPC155552
0.7697	Intermediate Similarity	NPC51181
0.7697	Intermediate Similarity	NPC477956
0.7692	Intermediate Similarity	NPC81835
0.7692	Intermediate Similarity	NPC119767
0.7688	Intermediate Similarity	NPC159692
0.7682	Intermediate Similarity	NPC33144
0.7682	Intermediate Similarity	NPC191835
0.7682	Intermediate Similarity	NPC153979
0.7682	Intermediate Similarity	NPC94248
0.7682	Intermediate Similarity	NPC478200
0.7682	Intermediate Similarity	NPC317119
0.7682	Intermediate Similarity	NPC212693
0.7682	Intermediate Similarity	NPC472602
0.7677	Intermediate Similarity	NPC471524
0.7677	Intermediate Similarity	NPC29577
0.7677	Intermediate Similarity	NPC476055
0.7677	Intermediate Similarity	NPC328623
0.7677	Intermediate Similarity	NPC469935
0.7677	Intermediate Similarity	NPC206212
0.7677	Intermediate Similarity	NPC196137
0.7677	Intermediate Similarity	NPC469953
0.7677	Intermediate Similarity	NPC71184
0.7677	Intermediate Similarity	NPC471473
0.7677	Intermediate Similarity	NPC178627
0.7677	Intermediate Similarity	NPC1886
0.7677	Intermediate Similarity	NPC471523
0.7676	Intermediate Similarity	NPC121168
0.7671	Intermediate Similarity	NPC276238
0.7671	Intermediate Similarity	NPC171460
0.7671	Intermediate Similarity	NPC303910
0.7671	Intermediate Similarity	NPC474998
0.7667	Intermediate Similarity	NPC163029
0.7667	Intermediate Similarity	NPC326847
0.7667	Intermediate Similarity	NPC158481
0.7667	Intermediate Similarity	NPC249817
0.7667	Intermediate Similarity	NPC118919
0.7667	Intermediate Similarity	NPC475111
0.7662	Intermediate Similarity	NPC471731
0.7662	Intermediate Similarity	NPC472610
0.7662	Intermediate Similarity	NPC297600

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 NPC271451 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	298
0.1-0.2	940
0.2-0.3	1453
0.3-0.4	2669
0.4-0.5	2198
0.5-0.6	1158
0.6-0.7	395
0.7-0.8	39
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
0.7986	Intermediate Similarity	NPD3764	Approved
0.7826	Intermediate Similarity	NPD9545	Approved
0.7815	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7763	Intermediate Similarity	NPD4628	Phase 3
0.7667	Intermediate Similarity	NPD2799	Discontinued
0.7647	Intermediate Similarity	NPD7003	Approved
0.7595	Intermediate Similarity	NPD7458	Discontinued
0.7532	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7532	Intermediate Similarity	NPD3750	Approved
0.7518	Intermediate Similarity	NPD4196	Clinical (unspecified phase)
0.7516	Intermediate Similarity	NPD7819	Suspended
0.7516	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD2935	Discontinued
0.7469	Intermediate Similarity	NPD4288	Approved
0.7378	Intermediate Similarity	NPD7075	Discontinued
0.7342	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7342	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7317	Intermediate Similarity	NPD7768	Phase 2
0.731	Intermediate Similarity	NPD1608	Approved
0.7308	Intermediate Similarity	NPD8166	Discontinued
0.7301	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7285	Intermediate Similarity	NPD1240	Approved
0.7284	Intermediate Similarity	NPD7411	Suspended
0.7279	Intermediate Similarity	NPD9265	Clinical (unspecified phase)
0.7279	Intermediate Similarity	NPD1164	Approved
0.7273	Intermediate Similarity	NPD6100	Approved
0.7273	Intermediate Similarity	NPD5406	Approved
0.7273	Intermediate Similarity	NPD5404	Approved
0.7273	Intermediate Similarity	NPD5405	Approved
0.7273	Intermediate Similarity	NPD5408	Approved
0.7273	Intermediate Similarity	NPD6099	Approved
0.7267	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7267	Intermediate Similarity	NPD3226	Approved
0.7256	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7233	Intermediate Similarity	NPD2532	Approved
0.7233	Intermediate Similarity	NPD2534	Approved
0.7233	Intermediate Similarity	NPD2533	Approved
0.7226	Intermediate Similarity	NPD6831	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD6599	Discontinued
0.7208	Intermediate Similarity	NPD3748	Approved
0.7208	Intermediate Similarity	NPD1510	Phase 2
0.7192	Intermediate Similarity	NPD3972	Approved
0.719	Intermediate Similarity	NPD1607	Approved
0.719	Intermediate Similarity	NPD6651	Approved
0.7183	Intermediate Similarity	NPD9493	Approved
0.7176	Intermediate Similarity	NPD7473	Discontinued
0.7169	Intermediate Similarity	NPD3749	Approved
0.7162	Intermediate Similarity	NPD2797	Approved
0.7152	Intermediate Similarity	NPD2313	Discontinued
0.7152	Intermediate Similarity	NPD2296	Approved
0.7152	Intermediate Similarity	NPD3268	Approved
0.7134	Intermediate Similarity	NPD2800	Approved
0.7124	Intermediate Similarity	NPD230	Phase 1
0.7118	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7117	Intermediate Similarity	NPD4380	Phase 2
0.7115	Intermediate Similarity	NPD2344	Approved
0.7115	Intermediate Similarity	NPD2346	Discontinued
0.7114	Intermediate Similarity	NPD2798	Approved
0.7105	Intermediate Similarity	NPD6663	Approved
0.7103	Intermediate Similarity	NPD17	Approved
0.7101	Intermediate Similarity	NPD6232	Discontinued
0.7097	Intermediate Similarity	NPD4308	Phase 3
0.7097	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7095	Intermediate Similarity	NPD1283	Approved
0.7086	Intermediate Similarity	NPD5952	Clinical (unspecified phase)
0.7081	Intermediate Similarity	NPD6273	Approved
0.707	Intermediate Similarity	NPD1549	Phase 2
0.7067	Intermediate Similarity	NPD5736	Approved
0.7063	Intermediate Similarity	NPD6799	Approved
0.7047	Intermediate Similarity	NPD1470	Approved
0.7047	Intermediate Similarity	NPD1203	Approved
0.7042	Intermediate Similarity	NPD5951	Approved
0.703	Intermediate Similarity	NPD6801	Discontinued
0.7019	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7013	Intermediate Similarity	NPD6355	Discontinued
0.7007	Intermediate Similarity	NPD1201	Approved
0.7006	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7006	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7006	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD7236	Approved
0.6994	Remote Similarity	NPD5844	Phase 1
0.6988	Remote Similarity	NPD2393	Clinical (unspecified phase)
0.6986	Remote Similarity	NPD2932	Approved
0.6986	Remote Similarity	NPD4626	Approved
0.6986	Remote Similarity	NPD3019	Approved
0.6983	Remote Similarity	NPD4287	Approved
0.6959	Remote Similarity	NPD9717	Approved
0.6957	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6951	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6948	Remote Similarity	NPD4060	Phase 1
0.6943	Remote Similarity	NPD4477	Approved
0.6943	Remote Similarity	NPD4476	Approved
0.6943	Remote Similarity	NPD1551	Phase 2
0.6943	Remote Similarity	NPD2796	Approved
0.6937	Remote Similarity	NPD2309	Approved
0.6918	Remote Similarity	NPD1243	Approved
0.6908	Remote Similarity	NPD6832	Phase 2
0.6905	Remote Similarity	NPD4868	Clinical (unspecified phase)
0.6892	Remote Similarity	NPD1281	Approved
0.6887	Remote Similarity	NPD6007	Clinical (unspecified phase)
0.6883	Remote Similarity	NPD8032	Phase 2
0.6879	Remote Similarity	NPD7033	Discontinued
0.6875	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.6872	Remote Similarity	NPD8150	Discontinued
0.6871	Remote Similarity	NPD5049	Phase 3
0.6867	Remote Similarity	NPD1876	Approved
0.6863	Remote Similarity	NPD7008	Discontinued
0.6863	Remote Similarity	NPD7095	Approved
0.6852	Remote Similarity	NPD7390	Discontinued
0.6839	Remote Similarity	NPD4307	Phase 2
0.6839	Remote Similarity	NPD943	Approved
0.6839	Remote Similarity	NPD2979	Phase 3
0.6839	Remote Similarity	NPD7177	Discontinued
0.6832	Remote Similarity	NPD6190	Approved
0.6832	Remote Similarity	NPD2354	Approved
0.6821	Remote Similarity	NPD3267	Approved
0.6821	Remote Similarity	NPD3266	Approved
0.6818	Remote Similarity	NPD5953	Discontinued
0.6803	Remote Similarity	NPD5691	Approved
0.68	Remote Similarity	NPD7286	Phase 2
0.6792	Remote Similarity	NPD6004	Phase 3
0.6792	Remote Similarity	NPD6005	Phase 3
0.6792	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.6792	Remote Similarity	NPD6002	Phase 3
0.6792	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.6788	Remote Similarity	NPD7239	Suspended
0.6786	Remote Similarity	NPD1465	Phase 2
0.6779	Remote Similarity	NPD422	Phase 1
0.6778	Remote Similarity	NPD8434	Phase 2
0.6765	Remote Similarity	NPD4381	Clinical (unspecified phase)
0.6757	Remote Similarity	NPD1778	Approved
0.6757	Remote Similarity	NPD7163	Clinical (unspecified phase)
0.6757	Remote Similarity	NPD3412	Clinical (unspecified phase)
0.6755	Remote Similarity	NPD3225	Approved
0.6748	Remote Similarity	NPD1511	Approved
0.6744	Remote Similarity	NPD8127	Discontinued
0.6744	Remote Similarity	NPD6959	Discontinued
0.6739	Remote Similarity	NPD1930	Approved
0.6739	Remote Similarity	NPD1931	Clinical (unspecified phase)
0.6739	Remote Similarity	NPD1929	Approved
0.6738	Remote Similarity	NPD9266	Approved
0.6738	Remote Similarity	NPD74	Approved
0.6733	Remote Similarity	NPD1481	Phase 2
0.6727	Remote Similarity	NPD920	Approved
0.6726	Remote Similarity	NPD1934	Approved
0.6722	Remote Similarity	NPD8055	Clinical (unspecified phase)
0.6721	Remote Similarity	NPD7879	Clinical (unspecified phase)
0.6712	Remote Similarity	NPD405	Clinical (unspecified phase)
0.671	Remote Similarity	NPD4907	Clinical (unspecified phase)
0.671	Remote Similarity	NPD6798	Discontinued
0.6706	Remote Similarity	NPD3882	Suspended
0.6705	Remote Similarity	NPD5710	Approved
0.6705	Remote Similarity	NPD5711	Approved
0.6705	Remote Similarity	NPD7229	Phase 3
0.6705	Remote Similarity	NPD7804	Clinical (unspecified phase)
0.6703	Remote Similarity	NPD8397	Clinical (unspecified phase)
0.6689	Remote Similarity	NPD3600	Clinical (unspecified phase)
0.6688	Remote Similarity	NPD5124	Phase 1
0.6688	Remote Similarity	NPD5123	Clinical (unspecified phase)
0.6687	Remote Similarity	NPD2353	Approved
0.6687	Remote Similarity	NPD643	Clinical (unspecified phase)
0.6687	Remote Similarity	NPD6666	Approved
0.6687	Remote Similarity	NPD2355	Clinical (unspecified phase)
0.6687	Remote Similarity	NPD6667	Approved
0.6686	Remote Similarity	NPD5761	Phase 2
0.6686	Remote Similarity	NPD5760	Phase 2
0.6686	Remote Similarity	NPD2801	Approved
0.6667	Remote Similarity	NPD6873	Phase 2
0.6667	Remote Similarity	NPD7615	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD9263	Approved
0.6667	Remote Similarity	NPD9267	Approved
0.6667	Remote Similarity	NPD9264	Approved
0.6667	Remote Similarity	NPD1512	Approved
0.6667	Remote Similarity	NPD1535	Discovery
0.6648	Remote Similarity	NPD7893	Clinical (unspecified phase)
0.6647	Remote Similarity	NPD8438	Clinical (unspecified phase)
0.6647	Remote Similarity	NPD3817	Phase 2
0.6645	Remote Similarity	NPD6696	Suspended
0.6643	Remote Similarity	NPD2181	Clinical (unspecified phase)
0.6642	Remote Similarity	NPD3020	Approved
0.6629	Remote Similarity	NPD3451	Clinical (unspecified phase)
0.6627	Remote Similarity	NPD6980	Clinical (unspecified phase)
0.6626	Remote Similarity	NPD3887	Approved
0.6625	Remote Similarity	NPD2438	Suspended
0.6625	Remote Similarity	NPD2531	Phase 2
0.6623	Remote Similarity	NPD9269	Phase 2
0.662	Remote Similarity	NPD2182	Approved
0.6611	Remote Similarity	NPD8312	Approved
0.6611	Remote Similarity	NPD8313	Approved
0.6606	Remote Similarity	NPD642	Clinical (unspecified phase)
0.6606	Remote Similarity	NPD7422	Clinical (unspecified phase)
0.6603	Remote Similarity	NPD411	Approved
0.66	Remote Similarity	NPD3026	Approved
0.66	Remote Similarity	NPD3847	Discontinued
0.66	Remote Similarity	NPD3023	Approved
0.6597	Remote Similarity	NPD1609	Clinical (unspecified phase)
0.6592	Remote Similarity	NPD7685	Pre-registration
0.659	Remote Similarity	NPD5494	Approved
0.6588	Remote Similarity	NPD8455	Phase 2
0.6587	Remote Similarity	NPD2370	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