NPASS Compound

Structure

NPC474678 OpenBabel07101718312D 35 37 0 0 1 0 0 0 0 0999 V2000 -4.3577 -1.6441 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6808 -2.7024 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8147 -3.2024 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5468 -3.2024 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.0109 -3.2024 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.1449 -4.7024 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8373 -1.8074 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.8769 -5.7024 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0185 0.1040 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.0109 -4.2024 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.1449 -2.7024 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.2788 -4.2024 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7837 -2.1306 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7309 -0.5977 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.8769 -4.7024 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 1.0827 -1.2024 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6264 -1.5923 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.2788 -3.2024 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1691 -1.6092 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.9487 -1.7024 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5000 -0.8660 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 7.1449 -1.7024 0.0000 Br 0 0 0 0 0 0 0 0 0 0 0 0 5.4128 -4.7024 0.0000 Br 0 0 0 0 0 0 0 0 0 0 0 0 -1.9031 -3.1235 0.0000 Br 0 0 0 0 0 0 0 0 0 0 0 0 -3.6723 -0.2604 0.0000 Br 0 0 0 0 0 0 0 0 0 0 0 0 8.0109 -6.2024 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 1.9487 -2.7024 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 0.9781 -0.2079 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 9.7429 -4.2024 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0388 -2.5873 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.8147 -1.2024 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4771 -2.1180 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.4128 -2.7024 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.0257 -0.0153 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 32 1 0 0 0 0 2 3 1 0 0 0 0 2 4 1 0 0 0 0 3 27 1 0 0 0 0 4 33 1 0 0 0 0 5 10 2 0 0 0 0 5 11 1 0 0 0 0 6 10 1 0 0 0 0 6 12 2 0 0 0 0 7 13 1 0 0 0 0 8 15 1 0 0 0 0 8 26 1 0 0 0 0 9 14 2 0 0 0 0 9 34 1 0 0 0 0 10 15 1 0 0 0 0 11 18 2 0 0 0 0 11 22 1 0 0 0 0 12 18 1 0 0 0 0 12 23 1 0 0 0 0 13 17 2 0 0 0 0 13 24 1 0 0 0 0 14 17 1 0 0 0 0 14 25 1 0 0 0 0 15 29 1 0 0 0 0 16 19 1 0 0 0 0 16 20 1 0 0 0 0 16 28 2 0 0 0 0 17 32 1 0 0 0 0 18 33 1 0 0 0 0 19 21 1 6 0 0 0 19 30 1 0 0 0 0 20 27 1 0 0 0 0 20 31 2 0 0 0 0 21 7 1 6 0 0 0 21 34 1 0 0 0 0 21 35 1 0 0 0 0 28 35 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	744.83
Volume:	499.304
LogP:	2.959
LogD:	1.719
LogS:	-2.515
# Rotatable Bonds:	10
TPSA:	141.37
# H-Bond Aceptor:	10
# H-Bond Donor:	5
# Rings:	3
# Heavy Atoms:	14

MedChem Properties

QED Drug-Likeness Score:	0.222
Synthetic Accessibility Score:	5.121
Fsp3:	0.429
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.369
MDCK Permeability:	2.296033017046284e-05
Pgp-inhibitor:	0.076
Pgp-substrate:	0.005
Human Intestinal Absorption (HIA):	0.622
20% Bioavailability (F20%):	0.992
30% Bioavailability (F30%):	0.998

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.529
Plasma Protein Binding (PPB):	93.14025115966797%
Volume Distribution (VD):	0.934
Pgp-substrate:	9.609975814819336%

ADMET: Metabolism

CYP1A2-inhibitor:	0.451
CYP1A2-substrate:	0.503
CYP2C19-inhibitor:	0.651
CYP2C19-substrate:	0.662
CYP2C9-inhibitor:	0.492
CYP2C9-substrate:	0.09
CYP2D6-inhibitor:	0.204
CYP2D6-substrate:	0.204
CYP3A4-inhibitor:	0.942
CYP3A4-substrate:	0.724

ADMET: Excretion

Clearance (CL):	1.469
Half-life (T1/2):	0.257

ADMET: Toxicity

hERG Blockers:	0.238
Human Hepatotoxicity (H-HT):	0.185
Drug-inuced Liver Injury (DILI):	0.454
AMES Toxicity:	0.434
Rat Oral Acute Toxicity:	0.73
Maximum Recommended Daily Dose:	0.944
Skin Sensitization:	0.295
Carcinogencity:	0.856
Eye Corrosion:	0.003
Eye Irritation:	0.005
Respiratory Toxicity:	0.954

Download Data

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

Natural Product: NPC474678

Natural Product ID:	NPC474678
*Common Name:**	Psammaplysin B
IUPAC Name:	(4S,5S)-N-[3-[4-(2-amino-1-hydroxyethyl)-2,6-dibromophenoxy]propyl]-7,9-dibromo-4-hydroxy-8-methoxy-1,11-dioxa-2-azaspiro[4.6]undeca-2,7,9-triene-3-carboxamide
Synonyms:
Standard InCHIKey:	REZAYKBREJXSAG-XHRKEWCOSA-N
Standard InCHI:	InChI=1S/C21H23Br4N3O7/c1-32-17-13(24)7-21(34-9-14(17)25)19(30)16(28-35-21)20(31)27-3-2-4-33-18-11(22)5-10(6-12(18)23)15(29)8-26/h5-6,9,15,19,29-30H,2-4,7-8,26H2,1H3,(H,27,31)/t15?,19-,21-/m0/s1
SMILES:	NCC(c1cc(Br)c(c(c1)Br)OCCCNC(=O)C1=NO[C@@]2([C@H]1O)OC=C(C(=C(C2)Br)OC)Br)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL479148
PubChem CID:	10259505
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0002341] Phenol ethers

*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
NPO32805	Druinella purpurea	Species	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[1522422]
NPO32805	Druinella purpurea	Species	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[1791478]

☑ 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
NPT393	Cell Line	HCT-116	Homo sapiens	IC50	=	6.0	ug.mL-1	PMID[485990]

☑ 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 NPC474678 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	236
0.1-0.2	1503
0.2-0.3	8558
0.3-0.4	10141
0.4-0.5	13545
0.5-0.6	8342
0.6-0.7	320
0.7-0.8	24
0.8-0.85	7
0.85-0.9	13
0.9-0.95	2
0.95-1	6

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC471338
0.9942	High Similarity	NPC475843
0.9661	High Similarity	NPC471337
0.9649	High Similarity	NPC8093
0.9649	High Similarity	NPC121571
0.9293	High Similarity	NPC470746
0.9293	High Similarity	NPC471336
0.9016	High Similarity	NPC123140
0.9006	High Similarity	NPC477255
0.8953	High Similarity	NPC471335
0.8876	High Similarity	NPC259071
0.8876	High Similarity	NPC77435
0.8764	High Similarity	NPC477254
0.8689	High Similarity	NPC227953
0.8684	High Similarity	NPC471339
0.8541	High Similarity	NPC202866
0.8415	Intermediate Similarity	NPC174607
0.837	Intermediate Similarity	NPC147847
0.8035	Intermediate Similarity	NPC469711
0.7797	Intermediate Similarity	NPC156311
0.7544	Intermediate Similarity	NPC474673
0.7472	Intermediate Similarity	NPC258222
0.743	Intermediate Similarity	NPC47672
0.7403	Intermediate Similarity	NPC233926
0.7399	Intermediate Similarity	NPC128877
0.7371	Intermediate Similarity	NPC308571
0.7318	Intermediate Similarity	NPC76412
0.7278	Intermediate Similarity	NPC109968
0.7172	Intermediate Similarity	NPC248822
0.7135	Intermediate Similarity	NPC78530
0.7107	Intermediate Similarity	NPC475658
0.7107	Intermediate Similarity	NPC473892
0.7071	Intermediate Similarity	NPC82741
0.7071	Intermediate Similarity	NPC473409
0.7071	Intermediate Similarity	NPC246591
0.7071	Intermediate Similarity	NPC141405
0.7059	Intermediate Similarity	NPC473450
0.7047	Intermediate Similarity	NPC143450
0.7039	Intermediate Similarity	NPC135349
0.7029	Intermediate Similarity	NPC470471
0.7022	Intermediate Similarity	NPC474128
0.702	Intermediate Similarity	NPC471591
0.7017	Intermediate Similarity	NPC71629
0.697	Remote Similarity	NPC49172
0.6965	Remote Similarity	NPC102245
0.6949	Remote Similarity	NPC470470
0.6944	Remote Similarity	NPC470472
0.6923	Remote Similarity	NPC296085
0.6897	Remote Similarity	NPC469721
0.6897	Remote Similarity	NPC80514
0.6881	Remote Similarity	NPC64066
0.6866	Remote Similarity	NPC283207
0.6857	Remote Similarity	NPC307123
0.6857	Remote Similarity	NPC247018
0.6857	Remote Similarity	NPC97870
0.685	Remote Similarity	NPC96275
0.6842	Remote Similarity	NPC272463
0.6828	Remote Similarity	NPC73132
0.6828	Remote Similarity	NPC471235
0.6828	Remote Similarity	NPC235033
0.6806	Remote Similarity	NPC469479
0.6802	Remote Similarity	NPC110131
0.6788	Remote Similarity	NPC473693
0.6788	Remote Similarity	NPC471568
0.6788	Remote Similarity	NPC196091
0.6765	Remote Similarity	NPC65714
0.6748	Remote Similarity	NPC469731
0.6701	Remote Similarity	NPC226001
0.6701	Remote Similarity	NPC469979
0.67	Remote Similarity	NPC230539
0.6683	Remote Similarity	NPC80337
0.6667	Remote Similarity	NPC298981
0.6667	Remote Similarity	NPC299806
0.6667	Remote Similarity	NPC110454
0.6667	Remote Similarity	NPC471592
0.6667	Remote Similarity	NPC126128
0.6667	Remote Similarity	NPC326027
0.6667	Remote Similarity	NPC473462
0.6667	Remote Similarity	NPC207819
0.6651	Remote Similarity	NPC326333
0.6648	Remote Similarity	NPC204546
0.6613	Remote Similarity	NPC20755
0.66	Remote Similarity	NPC475396
0.6573	Remote Similarity	NPC474753
0.6567	Remote Similarity	NPC301941
0.6567	Remote Similarity	NPC214188
0.6567	Remote Similarity	NPC74618
0.6566	Remote Similarity	NPC225130
0.6564	Remote Similarity	NPC186617
0.6555	Remote Similarity	NPC477552
0.6555	Remote Similarity	NPC477550
0.6538	Remote Similarity	NPC40321
0.6524	Remote Similarity	NPC123859
0.6524	Remote Similarity	NPC324081
0.6517	Remote Similarity	NPC473724
0.6517	Remote Similarity	NPC475735
0.6514	Remote Similarity	NPC320242
0.6502	Remote Similarity	NPC315542
0.6493	Remote Similarity	NPC477551
0.6493	Remote Similarity	NPC242728
0.6492	Remote Similarity	NPC56635
0.6484	Remote Similarity	NPC213471
0.648	Remote Similarity	NPC470392
0.648	Remote Similarity	NPC469505
0.6476	Remote Similarity	NPC323662
0.6471	Remote Similarity	NPC276120
0.6468	Remote Similarity	NPC290534
0.6462	Remote Similarity	NPC214368
0.6461	Remote Similarity	NPC474087
0.6461	Remote Similarity	NPC474091
0.6439	Remote Similarity	NPC144823
0.6432	Remote Similarity	NPC471165
0.6429	Remote Similarity	NPC144314
0.6429	Remote Similarity	NPC209463
0.6418	Remote Similarity	NPC475421
0.6417	Remote Similarity	NPC313414
0.6413	Remote Similarity	NPC470709
0.6398	Remote Similarity	NPC50548
0.6393	Remote Similarity	NPC197045
0.6385	Remote Similarity	NPC156055
0.6383	Remote Similarity	NPC132771
0.6381	Remote Similarity	NPC149962
0.6378	Remote Similarity	NPC254700
0.6372	Remote Similarity	NPC81845
0.6364	Remote Similarity	NPC328763
0.6354	Remote Similarity	NPC163810
0.6354	Remote Similarity	NPC132308
0.6354	Remote Similarity	NPC169766
0.6346	Remote Similarity	NPC477526
0.6345	Remote Similarity	NPC473502
0.6343	Remote Similarity	NPC116562
0.6341	Remote Similarity	NPC138083
0.6332	Remote Similarity	NPC89831
0.6328	Remote Similarity	NPC141739
0.6328	Remote Similarity	NPC136112
0.6327	Remote Similarity	NPC158900
0.6327	Remote Similarity	NPC472923
0.6327	Remote Similarity	NPC63931
0.6324	Remote Similarity	NPC470112
0.6324	Remote Similarity	NPC470903
0.6324	Remote Similarity	NPC167763
0.6319	Remote Similarity	NPC303993
0.6302	Remote Similarity	NPC123011
0.6302	Remote Similarity	NPC256689
0.6302	Remote Similarity	NPC476268
0.6296	Remote Similarity	NPC14339
0.6289	Remote Similarity	NPC287757
0.6289	Remote Similarity	NPC319320
0.6284	Remote Similarity	NPC196708
0.628	Remote Similarity	NPC94862
0.6279	Remote Similarity	NPC311357
0.6256	Remote Similarity	NPC476194
0.6256	Remote Similarity	NPC59827
0.6256	Remote Similarity	NPC477160
0.6256	Remote Similarity	NPC184933
0.625	Remote Similarity	NPC470249
0.625	Remote Similarity	NPC473055
0.625	Remote Similarity	NPC473052
0.625	Remote Similarity	NPC470951
0.625	Remote Similarity	NPC328494
0.625	Remote Similarity	NPC470248
0.6243	Remote Similarity	NPC11449
0.6238	Remote Similarity	NPC477115
0.6237	Remote Similarity	NPC81137
0.6237	Remote Similarity	NPC251439
0.6237	Remote Similarity	NPC469360
0.6233	Remote Similarity	NPC67658
0.6231	Remote Similarity	NPC280022
0.6227	Remote Similarity	NPC295795
0.6225	Remote Similarity	NPC32064
0.6223	Remote Similarity	NPC178466
0.6223	Remote Similarity	NPC63628
0.622	Remote Similarity	NPC29531
0.6219	Remote Similarity	NPC273755
0.6218	Remote Similarity	NPC244509
0.6218	Remote Similarity	NPC476741
0.6218	Remote Similarity	NPC470710
0.6216	Remote Similarity	NPC322526
0.62	Remote Similarity	NPC46009
0.6197	Remote Similarity	NPC281629
0.6196	Remote Similarity	NPC6570
0.6196	Remote Similarity	NPC235633
0.619	Remote Similarity	NPC473378
0.619	Remote Similarity	NPC473407
0.6188	Remote Similarity	NPC164608
0.6188	Remote Similarity	NPC26108
0.6186	Remote Similarity	NPC471073
0.6186	Remote Similarity	NPC270811
0.6184	Remote Similarity	NPC206061
0.6182	Remote Similarity	NPC293347
0.618	Remote Similarity	NPC95733
0.618	Remote Similarity	NPC62101
0.6176	Remote Similarity	NPC475615
0.6175	Remote Similarity	NPC243404
0.6173	Remote Similarity	NPC471203
0.6173	Remote Similarity	NPC37205
0.6173	Remote Similarity	NPC160931
0.6172	Remote Similarity	NPC471395
0.6172	Remote Similarity	NPC124626
0.6168	Remote Similarity	NPC477527

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 NPC474678 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	148
0.1-0.2	567
0.2-0.3	1508
0.3-0.4	2528
0.4-0.5	2919
0.5-0.6	1352
0.6-0.7	128
0.7-0.8	0
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
0.691	Remote Similarity	NPD2240	Approved
0.691	Remote Similarity	NPD2239	Approved
0.6857	Remote Similarity	NPD1423	Approved
0.6793	Remote Similarity	NPD3536	Discontinued
0.6768	Remote Similarity	NPD5192	Clinical (unspecified phase)
0.6743	Remote Similarity	NPD3180	Approved
0.6743	Remote Similarity	NPD3179	Approved
0.6703	Remote Similarity	NPD2976	Clinical (unspecified phase)
0.6701	Remote Similarity	NPD7608	Discontinued
0.6596	Remote Similarity	NPD3686	Approved
0.6596	Remote Similarity	NPD3687	Approved
0.6556	Remote Similarity	NPD3054	Approved
0.6556	Remote Similarity	NPD3052	Approved
0.6554	Remote Similarity	NPD9718	Approved
0.6543	Remote Similarity	NPD7131	Phase 3
0.6538	Remote Similarity	NPD3175	Clinical (unspecified phase)
0.6514	Remote Similarity	NPD1820	Approved
0.6514	Remote Similarity	NPD1819	Approved
0.6514	Remote Similarity	NPD1818	Approved
0.6514	Remote Similarity	NPD1817	Approved
0.6495	Remote Similarity	NPD8031	Discontinued
0.6492	Remote Similarity	NPD2541	Clinical (unspecified phase)
0.648	Remote Similarity	NPD7485	Phase 3
0.648	Remote Similarity	NPD7484	Phase 3
0.6471	Remote Similarity	NPD3154	Approved
0.6471	Remote Similarity	NPD3153	Approved
0.6465	Remote Similarity	NPD3451	Clinical (unspecified phase)
0.6461	Remote Similarity	NPD3165	Approved
0.6461	Remote Similarity	NPD3164	Approved
0.6461	Remote Similarity	NPD3167	Approved
0.6461	Remote Similarity	NPD3166	Approved
0.6436	Remote Similarity	NPD3985	Discontinued
0.6436	Remote Similarity	NPD5348	Clinical (unspecified phase)
0.6425	Remote Similarity	NPD5773	Approved
0.6425	Remote Similarity	NPD5772	Approved
0.642	Remote Similarity	NPD1770	Clinical (unspecified phase)
0.6406	Remote Similarity	NPD6677	Suspended
0.6406	Remote Similarity	NPD6072	Discontinued
0.6394	Remote Similarity	NPD5165	Clinical (unspecified phase)
0.6378	Remote Similarity	NPD6315	Phase 2
0.6364	Remote Similarity	NPD2677	Approved
0.6364	Remote Similarity	NPD4466	Phase 1
0.6359	Remote Similarity	NPD1725	Approved
0.6355	Remote Similarity	NPD7038	Approved
0.6355	Remote Similarity	NPD7039	Approved
0.6349	Remote Similarity	NPD3158	Phase 1
0.6349	Remote Similarity	NPD3157	Approved
0.6349	Remote Similarity	NPD4662	Approved
0.6349	Remote Similarity	NPD4661	Approved
0.6345	Remote Similarity	NPD4666	Phase 3
0.6344	Remote Similarity	NPD4162	Approved
0.634	Remote Similarity	NPD3465	Clinical (unspecified phase)
0.634	Remote Similarity	NPD7972	Discontinued
0.6337	Remote Similarity	NPD5557	Phase 1
0.6333	Remote Similarity	NPD3056	Clinical (unspecified phase)
0.6328	Remote Similarity	NPD1794	Approved
0.6316	Remote Similarity	NPD1975	Clinical (unspecified phase)
0.6316	Remote Similarity	NPD2184	Approved
0.6316	Remote Similarity	NPD2183	Approved
0.6316	Remote Similarity	NPD8059	Phase 3
0.6316	Remote Similarity	NPD8058	Clinical (unspecified phase)
0.6308	Remote Similarity	NPD7318	Phase 3
0.63	Remote Similarity	NPD4575	Clinical (unspecified phase)
0.6298	Remote Similarity	NPD3163	Approved
0.6298	Remote Similarity	NPD3162	Approved
0.6294	Remote Similarity	NPD5709	Phase 3
0.6291	Remote Similarity	NPD7811	Phase 3
0.6291	Remote Similarity	NPD7810	Phase 3
0.6289	Remote Similarity	NPD4018	Clinical (unspecified phase)
0.6289	Remote Similarity	NPD5356	Approved
0.6289	Remote Similarity	NPD5355	Approved
0.628	Remote Similarity	NPD3863	Clinical (unspecified phase)
0.6278	Remote Similarity	NPD5163	Phase 2
0.6275	Remote Similarity	NPD1298	Discontinued
0.6268	Remote Similarity	NPD5525	Clinical (unspecified phase)
0.6263	Remote Similarity	NPD2041	Clinical (unspecified phase)
0.6263	Remote Similarity	NPD6419	Discontinued
0.6263	Remote Similarity	NPD2042	Clinical (unspecified phase)
0.6257	Remote Similarity	NPD2459	Approved
0.6257	Remote Similarity	NPD2460	Phase 3
0.6257	Remote Similarity	NPD2458	Approved
0.6257	Remote Similarity	NPD3060	Approved
0.6256	Remote Similarity	NPD2977	Approved
0.6256	Remote Similarity	NPD2978	Approved
0.625	Remote Similarity	NPD2215	Approved
0.625	Remote Similarity	NPD2216	Approved
0.6243	Remote Similarity	NPD3281	Clinical (unspecified phase)
0.6238	Remote Similarity	NPD3909	Discontinued
0.6238	Remote Similarity	NPD6620	Discovery
0.623	Remote Similarity	NPD52	Approved
0.623	Remote Similarity	NPD7527	Clinical (unspecified phase)
0.623	Remote Similarity	NPD7526	Approved
0.622	Remote Similarity	NPD6377	Clinical (unspecified phase)
0.6218	Remote Similarity	NPD2651	Approved
0.6218	Remote Similarity	NPD2649	Approved
0.6211	Remote Similarity	NPD1774	Approved
0.6205	Remote Similarity	NPD7317	Phase 3
0.6203	Remote Similarity	NPD7153	Discontinued
0.6203	Remote Similarity	NPD7596	Clinical (unspecified phase)
0.6188	Remote Similarity	NPD3136	Phase 2
0.6188	Remote Similarity	NPD5605	Phase 2
0.6181	Remote Similarity	NPD2904	Discontinued
0.6178	Remote Similarity	NPD2874	Phase 2
0.6175	Remote Similarity	NPD3597	Clinical (unspecified phase)
0.6169	Remote Similarity	NPD5137	Approved
0.6167	Remote Similarity	NPD2250	Discontinued
0.6154	Remote Similarity	NPD7118	Clinical (unspecified phase)
0.615	Remote Similarity	NPD3656	Approved
0.615	Remote Similarity	NPD7978	Discontinued
0.6146	Remote Similarity	NPD2186	Approved
0.6146	Remote Similarity	NPD4186	Clinical (unspecified phase)
0.6129	Remote Similarity	NPD6863	Phase 2
0.6127	Remote Similarity	NPD42	Phase 2
0.6127	Remote Similarity	NPD6042	Phase 2
0.6126	Remote Similarity	NPD6087	Phase 1
0.6124	Remote Similarity	NPD3857	Clinical (unspecified phase)
0.6124	Remote Similarity	NPD3676	Clinical (unspecified phase)
0.612	Remote Similarity	NPD2245	Discovery
0.612	Remote Similarity	NPD1726	Clinical (unspecified phase)
0.612	Remote Similarity	NPD5745	Approved
0.6108	Remote Similarity	NPD1772	Clinical (unspecified phase)
0.6106	Remote Similarity	NPD6853	Approved
0.6106	Remote Similarity	NPD6851	Approved
0.6103	Remote Similarity	NPD7256	Discontinued
0.6096	Remote Similarity	NPD2161	Phase 2
0.6094	Remote Similarity	NPD3688	Clinical (unspecified phase)
0.6094	Remote Similarity	NPD3146	Approved
0.6094	Remote Similarity	NPD681	Clinical (unspecified phase)
0.6091	Remote Similarity	NPD6668	Clinical (unspecified phase)
0.6087	Remote Similarity	NPD3936	Clinical (unspecified phase)
0.6085	Remote Similarity	NPD5061	Approved
0.6085	Remote Similarity	NPD4237	Approved
0.6085	Remote Similarity	NPD5062	Approved
0.6085	Remote Similarity	NPD4236	Phase 3
0.6082	Remote Similarity	NPD4124	Clinical (unspecified phase)
0.6082	Remote Similarity	NPD4210	Discontinued
0.6078	Remote Similarity	NPD2163	Approved
0.6073	Remote Similarity	NPD3122	Phase 3
0.6073	Remote Similarity	NPD5295	Discontinued
0.6068	Remote Similarity	NPD6297	Approved
0.6066	Remote Similarity	NPD4258	Approved
0.6066	Remote Similarity	NPD4259	Approved
0.6064	Remote Similarity	NPD1375	Discontinued
0.6062	Remote Similarity	NPD2676	Approved
0.6062	Remote Similarity	NPD5261	Clinical (unspecified phase)
0.6062	Remote Similarity	NPD6390	Discontinued
0.6062	Remote Similarity	NPD7613	Discontinued
0.6062	Remote Similarity	NPD2675	Approved
0.6044	Remote Similarity	NPD2614	Approved
0.6043	Remote Similarity	NPD2154	Approved
0.6043	Remote Similarity	NPD2155	Approved
0.6043	Remote Similarity	NPD2156	Approved
0.6038	Remote Similarity	NPD3808	Clinical (unspecified phase)
0.6034	Remote Similarity	NPD3685	Discontinued
0.6032	Remote Similarity	NPD6681	Discovery
0.6031	Remote Similarity	NPD5586	Clinical (unspecified phase)
0.6029	Remote Similarity	NPD3366	Approved
0.6027	Remote Similarity	NPD7827	Phase 1
0.6022	Remote Similarity	NPD2653	Approved
0.6021	Remote Similarity	NPD5160	Discontinued
0.6018	Remote Similarity	NPD7584	Approved
0.6011	Remote Similarity	NPD5712	Approved
0.6011	Remote Similarity	NPD5746	Approved
0.601	Remote Similarity	NPD1771	Clinical (unspecified phase)
0.601	Remote Similarity	NPD7132	Clinical (unspecified phase)
0.601	Remote Similarity	NPD2802	Phase 3
0.6009	Remote Similarity	NPD7476	Discontinued
0.6009	Remote Similarity	NPD7296	Approved
0.6	Remote Similarity	NPD5940	Clinical (unspecified phase)
0.6	Remote Similarity	NPD856	Approved
0.6	Remote Similarity	NPD16	Approved
0.6	Remote Similarity	NPD196	Phase 1
0.599	Remote Similarity	NPD6666	Approved
0.599	Remote Similarity	NPD6667	Approved
0.5989	Remote Similarity	NPD5266	Clinical (unspecified phase)
0.598	Remote Similarity	NPD3556	Approved
0.598	Remote Similarity	NPD3557	Approved
0.598	Remote Similarity	NPD3558	Approved
0.598	Remote Similarity	NPD3559	Clinical (unspecified phase)
0.598	Remote Similarity	NPD3560	Approved
0.5978	Remote Similarity	NPD2562	Approved
0.5978	Remote Similarity	NPD2561	Approved
0.5963	Remote Similarity	NPD6519	Phase 2
0.5961	Remote Similarity	NPD7315	Approved
0.5946	Remote Similarity	NPD840	Approved
0.5946	Remote Similarity	NPD3532	Approved
0.5946	Remote Similarity	NPD3530	Approved
0.5946	Remote Similarity	NPD839	Approved
0.5946	Remote Similarity	NPD3531	Approved
0.5944	Remote Similarity	NPD2428	Approved
0.5944	Remote Similarity	NPD2429	Approved
0.5943	Remote Similarity	NPD3490	Discontinued
0.5943	Remote Similarity	NPD4157	Discontinued
0.5938	Remote Similarity	NPD2219	Phase 1
0.5933	Remote Similarity	NPD4419	Clinical (unspecified phase)
0.5931	Remote Similarity	NPD2388	Discontinued
0.5928	Remote Similarity	NPD4123	Phase 3
0.5926	Remote Similarity	NPD6032	Approved
0.5926	Remote Similarity	NPD1522	Approved
0.5926	Remote Similarity	NPD1537	Approved

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