NPASS Compound

Structure

NPC469498 OpenBabel07101719522D 32 35 0 0 1 0 0 0 0 0999 V2000 3.2709 -4.4563 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3504 2.4135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2165 1.9135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4899 -2.1473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7178 0.9509 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5388 -4.4563 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0732 -1.8248 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.9177 -2.6814 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6728 -3.9563 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4049 1.6180 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5388 1.1180 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0936 -2.0827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3994 -3.0608 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9511 -1.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4049 -3.9563 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.5003 -1.1691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3504 -2.7518 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4049 -2.9563 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1510 -3.0940 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3994 1.7226 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.6728 -2.9563 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.7431 -0.6691 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 5.5003 -0.1691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3504 1.4135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5388 -2.4563 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.9511 0.3090 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.5039 2.7171 0.0000 Br 0 0 0 0 0 0 0 0 0 0 0 0 -0.1932 -2.4563 0.0000 Br 0 0 0 0 0 0 0 0 0 0 0 0 5.1959 -4.0930 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.4785 0.0388 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 5.0936 0.7444 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 15 1 0 0 0 0 2 24 1 0 0 0 0 3 24 1 0 0 0 0 6 9 1 0 0 0 0 6 15 1 0 0 0 0 7 8 2 0 0 0 0 7 16 1 0 0 0 0 8 19 1 0 0 0 0 9 21 1 0 0 0 0 10 11 1 0 0 0 0 10 20 1 0 0 0 0 11 26 1 0 0 0 0 12 16 2 0 0 0 0 12 17 1 0 0 0 0 13 17 1 0 0 0 0 13 18 1 0 0 0 0 14 22 1 0 0 0 0 14 25 1 0 0 0 0 15 18 2 0 0 0 0 16 23 1 0 0 0 0 17 19 2 0 0 0 0 18 25 1 0 0 0 0 19 29 1 0 0 0 0 20 24 1 0 0 0 0 20 27 1 1 0 0 0 21 25 1 6 0 0 0 21 28 1 0 0 0 0 22 26 1 6 0 0 0 22 31 1 0 0 0 0 23 30 2 0 0 0 0 23 32 1 0 0 0 0 24 32 1 0 0 0 0 25 4 1 6 0 0 0 26 5 1 6 0 0 0 26 31 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	568.08
Volume:	484.572
LogP:	7.149
LogD:	4.232
LogS:	-3.959
# Rotatable Bonds:	0
TPSA:	59.06
# H-Bond Aceptor:	4
# H-Bond Donor:	1
# Rings:	4
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.16
Synthetic Accessibility Score:	5.947
Fsp3:	0.654
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:	-4.845
MDCK Permeability:	2.4869201297406107e-05
Pgp-inhibitor:	0.972
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.04
20% Bioavailability (F20%):	0.461
30% Bioavailability (F30%):	0.304

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.052
Plasma Protein Binding (PPB):	100.08899688720703%
Volume Distribution (VD):	1.608
Pgp-substrate:	1.5189787149429321%

ADMET: Metabolism

CYP1A2-inhibitor:	0.426
CYP1A2-substrate:	0.457
CYP2C19-inhibitor:	0.812
CYP2C19-substrate:	0.744
CYP2C9-inhibitor:	0.955
CYP2C9-substrate:	0.586
CYP2D6-inhibitor:	0.173
CYP2D6-substrate:	0.191
CYP3A4-inhibitor:	0.88
CYP3A4-substrate:	0.875

ADMET: Excretion

Clearance (CL):	8.756
Half-life (T1/2):	0.11

ADMET: Toxicity

hERG Blockers:	0.039
Human Hepatotoxicity (H-HT):	0.361
Drug-inuced Liver Injury (DILI):	0.549
AMES Toxicity:	0.078
Rat Oral Acute Toxicity:	0.541
Maximum Recommended Daily Dose:	0.91
Skin Sensitization:	0.858
Carcinogencity:	0.549
Eye Corrosion:	0.147
Eye Irritation:	0.459
Respiratory Toxicity:	0.975

Download Data

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

Natural Product: NPC469498

Natural Product ID:	NPC469498
*Common Name:**	Bromophycolide T
IUPAC Name:	n.a.
Synonyms:	Bromophycolide T
Standard InCHIKey:	SXQYDZYKXZHMKD-DGTHGUPJSA-N
Standard InCHI:	InChI=1S/C26H34Br2O4/c1-15-6-9-21(28)25(4)14-22-26(5,31-22)11-10-20(27)24(2,3)32-23(30)16-7-8-19(29)17(12-16)13-18(15)25/h7-8,12,20-22,29H,6,9-11,13-14H2,1-5H3/t20-,21+,22+,25+,26+/m1/s1
SMILES:	CC1=C2Cc3cc(ccc3O)C(=O)OC(C)(C)[C@@H](CC[C@@]3(C)[C@H](C[C@]2(C)[C@H](CC1)Br)O3)Br
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1081114
PubChem CID:	46880797
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	5
MIC	1

Activity Type	# Activity
Cell Line	1
Organism	5

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT116	Cell Line	HL-60	Homo sapiens	IC50	=	6000.0	nM	PMID[532879]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	8400.0	nM	PMID[532878]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	IC50	>	15000.0	nM	PMID[532878]
NPT1531	Organism	Enterococcus faecium	Enterococcus faecium	IC50	>	15000.0	nM	PMID[532878]
NPT88	Organism	Mycobacterium tuberculosis	Mycobacterium tuberculosis	MIC	>	50000.0	nM	PMID[532878]
NPT20	Organism	Candida albicans	Candida albicans	IC50	>	15000.0	nM	PMID[532878]

☑ 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 NPC469498 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	326
0.1-0.2	1415
0.2-0.3	3076
0.3-0.4	7524
0.4-0.5	11536
0.5-0.6	6046
0.6-0.7	10435
0.7-0.8	2308
0.8-0.85	18
0.85-0.9	7
0.9-0.95	4
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9786	High Similarity	NPC97188
0.9514	High Similarity	NPC52931
0.9444	High Similarity	NPC17600
0.9315	High Similarity	NPC37642
0.9252	High Similarity	NPC475093
0.9231	High Similarity	NPC271451
0.9122	High Similarity	NPC11892
0.8592	High Similarity	NPC302844
0.8561	High Similarity	NPC204579
0.8503	High Similarity	NPC469911
0.844	Intermediate Similarity	NPC473744
0.8429	Intermediate Similarity	NPC110211
0.8417	Intermediate Similarity	NPC184219
0.8392	Intermediate Similarity	NPC473777
0.8345	Intermediate Similarity	NPC174991
0.8273	Intermediate Similarity	NPC67300
0.8125	Intermediate Similarity	NPC117899
0.8117	Intermediate Similarity	NPC477483
0.8117	Intermediate Similarity	NPC325032
0.8117	Intermediate Similarity	NPC66991
0.8112	Intermediate Similarity	NPC121104
0.8105	Intermediate Similarity	NPC208293
0.8079	Intermediate Similarity	NPC184053
0.8077	Intermediate Similarity	NPC140133
0.8056	Intermediate Similarity	NPC193203
0.8056	Intermediate Similarity	NPC229894
0.8054	Intermediate Similarity	NPC119542
0.8052	Intermediate Similarity	NPC286038
0.8014	Intermediate Similarity	NPC475192
0.8014	Intermediate Similarity	NPC18798
0.8013	Intermediate Similarity	NPC327962
0.8013	Intermediate Similarity	NPC267469
0.8013	Intermediate Similarity	NPC162569
0.8013	Intermediate Similarity	NPC172311
0.8013	Intermediate Similarity	NPC179128
0.8013	Intermediate Similarity	NPC35160
0.8013	Intermediate Similarity	NPC87630
0.8013	Intermediate Similarity	NPC116292
0.8	Intermediate Similarity	NPC194979
0.8	Intermediate Similarity	NPC221104
0.7987	Intermediate Similarity	NPC258856
0.7987	Intermediate Similarity	NPC291454
0.7972	Intermediate Similarity	NPC49938
0.7961	Intermediate Similarity	NPC470842
0.7949	Intermediate Similarity	NPC279442
0.7945	Intermediate Similarity	NPC109778
0.7945	Intermediate Similarity	NPC86774
0.7945	Intermediate Similarity	NPC327457
0.7935	Intermediate Similarity	NPC473023
0.7933	Intermediate Similarity	NPC170718
0.7933	Intermediate Similarity	NPC477592
0.7931	Intermediate Similarity	NPC2596
0.7922	Intermediate Similarity	NPC151607
0.7922	Intermediate Similarity	NPC42540
0.7914	Intermediate Similarity	NPC273282
0.7914	Intermediate Similarity	NPC161943
0.7914	Intermediate Similarity	NPC474890
0.7914	Intermediate Similarity	NPC94298
0.7914	Intermediate Similarity	NPC27633
0.7911	Intermediate Similarity	NPC48671
0.7898	Intermediate Similarity	NPC247219
0.7895	Intermediate Similarity	NPC472600
0.7895	Intermediate Similarity	NPC472601
0.7881	Intermediate Similarity	NPC477593
0.7871	Intermediate Similarity	NPC75295
0.7867	Intermediate Similarity	NPC475111
0.7857	Intermediate Similarity	NPC159721
0.7852	Intermediate Similarity	NPC194970
0.7852	Intermediate Similarity	NPC477594
0.7847	Intermediate Similarity	NPC137416
0.7843	Intermediate Similarity	NPC472603
0.7843	Intermediate Similarity	NPC477595
0.7843	Intermediate Similarity	NPC472605
0.7843	Intermediate Similarity	NPC472604
0.7829	Intermediate Similarity	NPC473988
0.7815	Intermediate Similarity	NPC70380
0.7815	Intermediate Similarity	NPC194579
0.7815	Intermediate Similarity	NPC71256
0.7808	Intermediate Similarity	NPC2401
0.7806	Intermediate Similarity	NPC210966
0.7806	Intermediate Similarity	NPC478203
0.7806	Intermediate Similarity	NPC260152
0.7806	Intermediate Similarity	NPC126882
0.78	Intermediate Similarity	NPC27407
0.78	Intermediate Similarity	NPC477596
0.78	Intermediate Similarity	NPC142027
0.7793	Intermediate Similarity	NPC473751
0.7792	Intermediate Similarity	NPC308572
0.7785	Intermediate Similarity	NPC239855
0.777	Intermediate Similarity	NPC83718
0.777	Intermediate Similarity	NPC131192
0.7764	Intermediate Similarity	NPC472807
0.7763	Intermediate Similarity	NPC212693
0.7763	Intermediate Similarity	NPC478200
0.7763	Intermediate Similarity	NPC33144
0.7763	Intermediate Similarity	NPC472602
0.7763	Intermediate Similarity	NPC23870
0.7763	Intermediate Similarity	NPC94248
0.7763	Intermediate Similarity	NPC191835
0.7756	Intermediate Similarity	NPC257558
0.7756	Intermediate Similarity	NPC83272
0.7742	Intermediate Similarity	NPC472610
0.7742	Intermediate Similarity	NPC471731
0.7742	Intermediate Similarity	NPC478202
0.7742	Intermediate Similarity	NPC469615
0.774	Intermediate Similarity	NPC37512
0.7733	Intermediate Similarity	NPC204582
0.7727	Intermediate Similarity	NPC472035
0.7727	Intermediate Similarity	NPC158634
0.7727	Intermediate Similarity	NPC313123
0.7727	Intermediate Similarity	NPC478217
0.7727	Intermediate Similarity	NPC257003
0.7727	Intermediate Similarity	NPC53649
0.7727	Intermediate Similarity	NPC471444
0.7727	Intermediate Similarity	NPC478201
0.7718	Intermediate Similarity	NPC477407
0.7718	Intermediate Similarity	NPC165612
0.7718	Intermediate Similarity	NPC476389
0.7714	Intermediate Similarity	NPC122117
0.7712	Intermediate Similarity	NPC256463
0.7712	Intermediate Similarity	NPC112789
0.7712	Intermediate Similarity	NPC88269
0.7712	Intermediate Similarity	NPC295339
0.7712	Intermediate Similarity	NPC299405
0.7712	Intermediate Similarity	NPC306835
0.7712	Intermediate Similarity	NPC19622
0.7712	Intermediate Similarity	NPC111422
0.7712	Intermediate Similarity	NPC29771
0.7712	Intermediate Similarity	NPC216312
0.7712	Intermediate Similarity	NPC471602
0.7712	Intermediate Similarity	NPC476477
0.7697	Intermediate Similarity	NPC301915
0.7697	Intermediate Similarity	NPC261292
0.7692	Intermediate Similarity	NPC469683
0.7682	Intermediate Similarity	NPC477874
0.7682	Intermediate Similarity	NPC173569
0.7677	Intermediate Similarity	NPC471733
0.7662	Intermediate Similarity	NPC37992
0.7662	Intermediate Similarity	NPC42262
0.7662	Intermediate Similarity	NPC51181
0.7662	Intermediate Similarity	NPC220496
0.7662	Intermediate Similarity	NPC158472
0.7662	Intermediate Similarity	NPC64664
0.7662	Intermediate Similarity	NPC147542
0.7662	Intermediate Similarity	NPC241349
0.7662	Intermediate Similarity	NPC327916
0.7662	Intermediate Similarity	NPC275903
0.7662	Intermediate Similarity	NPC168471
0.7662	Intermediate Similarity	NPC32749
0.7658	Intermediate Similarity	NPC5568
0.7655	Intermediate Similarity	NPC221798
0.7651	Intermediate Similarity	NPC470831
0.7651	Intermediate Similarity	NPC15083
0.7651	Intermediate Similarity	NPC214702
0.7647	Intermediate Similarity	NPC61590
0.7632	Intermediate Similarity	NPC249817
0.7632	Intermediate Similarity	NPC235115
0.7628	Intermediate Similarity	NPC325346
0.7628	Intermediate Similarity	NPC476473
0.7625	Intermediate Similarity	NPC188403
0.7625	Intermediate Similarity	NPC180351
0.7625	Intermediate Similarity	NPC56204
0.7616	Intermediate Similarity	NPC27643
0.7616	Intermediate Similarity	NPC477893
0.7613	Intermediate Similarity	NPC477894
0.7613	Intermediate Similarity	NPC11056
0.7613	Intermediate Similarity	NPC67650
0.7613	Intermediate Similarity	NPC471587
0.7613	Intermediate Similarity	NPC1704
0.7606	Intermediate Similarity	NPC473767
0.7603	Intermediate Similarity	NPC165556
0.76	Intermediate Similarity	NPC323379
0.76	Intermediate Similarity	NPC327204
0.7597	Intermediate Similarity	NPC477055
0.7597	Intermediate Similarity	NPC139634
0.7597	Intermediate Similarity	NPC21350
0.7597	Intermediate Similarity	NPC32360
0.7597	Intermediate Similarity	NPC105456
0.7597	Intermediate Similarity	NPC477056
0.7595	Intermediate Similarity	NPC107625
0.7593	Intermediate Similarity	NPC62051
0.7593	Intermediate Similarity	NPC472799
0.7593	Intermediate Similarity	NPC470102
0.759	Intermediate Similarity	NPC473022
0.7584	Intermediate Similarity	NPC282230
0.7584	Intermediate Similarity	NPC123
0.7584	Intermediate Similarity	NPC183348
0.7584	Intermediate Similarity	NPC163169
0.7584	Intermediate Similarity	NPC245395
0.7582	Intermediate Similarity	NPC24394
0.7582	Intermediate Similarity	NPC22676
0.7582	Intermediate Similarity	NPC198621
0.7582	Intermediate Similarity	NPC216940
0.7582	Intermediate Similarity	NPC475482
0.758	Intermediate Similarity	NPC89664
0.758	Intermediate Similarity	NPC274085
0.7578	Intermediate Similarity	NPC221249
0.7578	Intermediate Similarity	NPC124842
0.7566	Intermediate Similarity	NPC61499
0.7564	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 NPC469498 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	278
0.1-0.2	955
0.2-0.3	1631
0.3-0.4	2678
0.4-0.5	2073
0.5-0.6	1135
0.6-0.7	366
0.7-0.8	34
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
0.7914	Intermediate Similarity	NPD9545	Approved
0.7778	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7727	Intermediate Similarity	NPD4628	Phase 3
0.7584	Intermediate Similarity	NPD3764	Approved
0.7455	Intermediate Similarity	NPD7075	Discontinued
0.7378	Intermediate Similarity	NPD7819	Suspended
0.7378	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7355	Intermediate Similarity	NPD2935	Discontinued
0.7346	Intermediate Similarity	NPD7458	Discontinued
0.7278	Intermediate Similarity	NPD7003	Approved
0.7278	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7278	Intermediate Similarity	NPD3750	Approved
0.7261	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7256	Intermediate Similarity	NPD7411	Suspended
0.7241	Intermediate Similarity	NPD4196	Clinical (unspecified phase)
0.7237	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7229	Intermediate Similarity	NPD4288	Approved
0.7208	Intermediate Similarity	NPD230	Phase 1
0.7205	Intermediate Similarity	NPD2532	Approved
0.7205	Intermediate Similarity	NPD2533	Approved
0.7205	Intermediate Similarity	NPD2534	Approved
0.7205	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7195	Intermediate Similarity	NPD4380	Phase 2
0.7194	Intermediate Similarity	NPD6831	Clinical (unspecified phase)
0.7186	Intermediate Similarity	NPD7768	Phase 2
0.7179	Intermediate Similarity	NPD1510	Phase 2
0.7179	Intermediate Similarity	NPD2799	Discontinued
0.717	Intermediate Similarity	NPD8166	Discontinued
0.7161	Intermediate Similarity	NPD6651	Approved
0.7153	Intermediate Similarity	NPD9493	Approved
0.7152	Intermediate Similarity	NPD1549	Phase 2
0.7143	Intermediate Similarity	NPD1240	Approved
0.7126	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7122	Intermediate Similarity	NPD9265	Clinical (unspecified phase)
0.7108	Intermediate Similarity	NPD6801	Discontinued
0.7099	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7091	Intermediate Similarity	NPD6599	Discontinued
0.7089	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7089	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7066	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7051	Intermediate Similarity	NPD1607	Approved
0.7037	Intermediate Similarity	NPD6799	Approved
0.7025	Intermediate Similarity	NPD2796	Approved
0.7	Intermediate Similarity	NPD2800	Approved
0.6994	Remote Similarity	NPD7852	Clinical (unspecified phase)
0.6982	Remote Similarity	NPD4868	Clinical (unspecified phase)
0.6975	Remote Similarity	NPD7236	Approved
0.6971	Remote Similarity	NPD5844	Phase 1
0.6968	Remote Similarity	NPD6663	Approved
0.6962	Remote Similarity	NPD7033	Discontinued
0.6962	Remote Similarity	NPD3748	Approved
0.6957	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.6951	Remote Similarity	NPD6273	Approved
0.6948	Remote Similarity	NPD5952	Clinical (unspecified phase)
0.6933	Remote Similarity	NPD3972	Approved
0.6928	Remote Similarity	NPD3226	Approved
0.6928	Remote Similarity	NPD5736	Approved
0.6918	Remote Similarity	NPD5406	Approved
0.6918	Remote Similarity	NPD5408	Approved
0.6918	Remote Similarity	NPD5404	Approved
0.6918	Remote Similarity	NPD5405	Approved
0.6918	Remote Similarity	NPD1551	Phase 2
0.6914	Remote Similarity	NPD6190	Approved
0.6908	Remote Similarity	NPD1164	Approved
0.6903	Remote Similarity	NPD2313	Discontinued
0.689	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6883	Remote Similarity	NPD6832	Phase 2
0.6879	Remote Similarity	NPD6232	Discontinued
0.6879	Remote Similarity	NPD6355	Discontinued
0.6857	Remote Similarity	NPD7473	Discontinued
0.6855	Remote Similarity	NPD4308	Phase 3
0.6851	Remote Similarity	NPD8150	Discontinued
0.6846	Remote Similarity	NPD4626	Approved
0.6846	Remote Similarity	NPD1778	Approved
0.6842	Remote Similarity	NPD3749	Approved
0.6842	Remote Similarity	NPD4381	Clinical (unspecified phase)
0.6839	Remote Similarity	NPD7008	Discontinued
0.6829	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6826	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6824	Remote Similarity	NPD2296	Approved
0.6821	Remote Similarity	NPD1608	Approved
0.6821	Remote Similarity	NPD9717	Approved
0.6813	Remote Similarity	NPD4476	Approved
0.6813	Remote Similarity	NPD4477	Approved
0.6813	Remote Similarity	NPD6099	Approved
0.6813	Remote Similarity	NPD6100	Approved
0.6807	Remote Similarity	NPD920	Approved
0.6805	Remote Similarity	NPD1934	Approved
0.6798	Remote Similarity	NPD5953	Discontinued
0.6797	Remote Similarity	NPD1203	Approved
0.6795	Remote Similarity	NPD6798	Discontinued
0.679	Remote Similarity	NPD1243	Approved
0.678	Remote Similarity	NPD7286	Phase 2
0.678	Remote Similarity	NPD7804	Clinical (unspecified phase)
0.6779	Remote Similarity	NPD5691	Approved
0.6776	Remote Similarity	NPD8397	Clinical (unspecified phase)
0.6772	Remote Similarity	NPD5124	Phase 1
0.6772	Remote Similarity	NPD5123	Clinical (unspecified phase)
0.677	Remote Similarity	NPD6002	Phase 3
0.677	Remote Similarity	NPD2344	Approved
0.677	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.677	Remote Similarity	NPD6005	Phase 3
0.677	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.677	Remote Similarity	NPD2346	Discontinued
0.677	Remote Similarity	NPD6004	Phase 3
0.677	Remote Similarity	NPD2343	Clinical (unspecified phase)
0.6768	Remote Similarity	NPD643	Clinical (unspecified phase)
0.6766	Remote Similarity	NPD7239	Suspended
0.6758	Remote Similarity	NPD8434	Phase 2
0.6753	Remote Similarity	NPD6007	Clinical (unspecified phase)
0.675	Remote Similarity	NPD1509	Clinical (unspecified phase)
0.6746	Remote Similarity	NPD7615	Clinical (unspecified phase)
0.6736	Remote Similarity	NPD2181	Clinical (unspecified phase)
0.6732	Remote Similarity	NPD1283	Approved
0.6724	Remote Similarity	NPD6959	Discontinued
0.6723	Remote Similarity	NPD7177	Discontinued
0.6712	Remote Similarity	NPD1241	Discontinued
0.6709	Remote Similarity	NPD4060	Phase 1
0.6707	Remote Similarity	NPD3887	Approved
0.6703	Remote Similarity	NPD7879	Clinical (unspecified phase)
0.6688	Remote Similarity	NPD3268	Approved
0.6688	Remote Similarity	NPD1470	Approved
0.6688	Remote Similarity	NPD2797	Approved
0.6687	Remote Similarity	NPD642	Clinical (unspecified phase)
0.6686	Remote Similarity	NPD5711	Approved
0.6686	Remote Similarity	NPD3882	Suspended
0.6686	Remote Similarity	NPD5710	Approved
0.6685	Remote Similarity	NPD4287	Approved
0.6667	Remote Similarity	NPD7685	Pre-registration
0.6667	Remote Similarity	NPD5951	Approved
0.6647	Remote Similarity	NPD5049	Phase 3
0.6645	Remote Similarity	NPD2798	Approved
0.6645	Remote Similarity	NPD422	Phase 1
0.6645	Remote Similarity	NPD1201	Approved
0.6629	Remote Similarity	NPD7893	Clinical (unspecified phase)
0.6629	Remote Similarity	NPD8127	Discontinued
0.6628	Remote Similarity	NPD3817	Phase 2
0.6627	Remote Similarity	NPD3455	Phase 2
0.6623	Remote Similarity	NPD8651	Approved
0.6623	Remote Similarity	NPD2932	Approved
0.6623	Remote Similarity	NPD3412	Clinical (unspecified phase)
0.6623	Remote Similarity	NPD17	Approved
0.6612	Remote Similarity	NPD8055	Clinical (unspecified phase)
0.6607	Remote Similarity	NPD5403	Approved
0.6606	Remote Similarity	NPD2354	Approved
0.6606	Remote Similarity	NPD2309	Approved
0.6604	Remote Similarity	NPD4307	Phase 2
0.6604	Remote Similarity	NPD2979	Phase 3
0.6604	Remote Similarity	NPD943	Approved
0.6603	Remote Similarity	NPD9494	Approved
0.6597	Remote Similarity	NPD9266	Approved
0.6597	Remote Similarity	NPD2182	Approved
0.6597	Remote Similarity	NPD74	Approved
0.6579	Remote Similarity	NPD3496	Discontinued
0.6577	Remote Similarity	NPD405	Clinical (unspecified phase)
0.6575	Remote Similarity	NPD6559	Discontinued
0.657	Remote Similarity	NPD2801	Approved
0.657	Remote Similarity	NPD5761	Phase 2
0.657	Remote Similarity	NPD8455	Phase 2
0.657	Remote Similarity	NPD5760	Phase 2
0.6566	Remote Similarity	NPD7440	Discontinued
0.6564	Remote Similarity	NPD7266	Discontinued
0.6556	Remote Similarity	NPD7074	Phase 3
0.6554	Remote Similarity	NPD2629	Approved
0.655	Remote Similarity	NPD6385	Approved
0.655	Remote Similarity	NPD6386	Approved
0.6536	Remote Similarity	NPD1547	Clinical (unspecified phase)
0.6536	Remote Similarity	NPD3818	Discontinued
0.6536	Remote Similarity	NPD1281	Approved
0.6528	Remote Similarity	NPD9264	Approved
0.6528	Remote Similarity	NPD9267	Approved
0.6528	Remote Similarity	NPD9263	Approved
0.6527	Remote Similarity	NPD1511	Approved
0.6527	Remote Similarity	NPD7390	Discontinued
0.6519	Remote Similarity	NPD7095	Approved
0.6519	Remote Similarity	NPD7993	Clinical (unspecified phase)
0.6517	Remote Similarity	NPD6168	Clinical (unspecified phase)
0.6517	Remote Similarity	NPD6167	Clinical (unspecified phase)
0.6517	Remote Similarity	NPD6166	Phase 2
0.6516	Remote Similarity	NPD1876	Approved
0.6516	Remote Similarity	NPD3225	Approved
0.6514	Remote Similarity	NPD919	Approved
0.6513	Remote Similarity	NPD7163	Clinical (unspecified phase)
0.6513	Remote Similarity	NPD3019	Approved
0.6509	Remote Similarity	NPD6980	Clinical (unspecified phase)
0.6509	Remote Similarity	NPD5586	Clinical (unspecified phase)
0.6503	Remote Similarity	NPD8313	Approved
0.6503	Remote Similarity	NPD2438	Suspended
0.6503	Remote Similarity	NPD8312	Approved
0.65	Remote Similarity	NPD7054	Approved
0.6497	Remote Similarity	NPD7229	Phase 3
0.6494	Remote Similarity	NPD1481	Phase 2
0.6494	Remote Similarity	NPD9269	Phase 2
0.649	Remote Similarity	NPD1894	Discontinued
0.6488	Remote Similarity	NPD5401	Approved
0.6484	Remote Similarity	NPD6764	Approved
0.6484	Remote Similarity	NPD6765	Approved
0.6481	Remote Similarity	NPD4978	Clinical (unspecified phase)
0.6481	Remote Similarity	NPD7097	Phase 1
0.6478	Remote Similarity	NPD4907	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