NPASS Compound

Structure

NPC475843 OpenBabel07101718322D 36 38 0 0 1 0 0 0 0 0999 V2000 8.0109 -7.2024 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -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 27 1 0 0 0 0 2 33 1 0 0 0 0 3 4 1 0 0 0 0 3 5 1 0 0 0 0 4 28 1 0 0 0 0 5 34 1 0 0 0 0 6 11 2 0 0 0 0 6 12 1 0 0 0 0 7 11 1 0 0 0 0 7 13 2 0 0 0 0 8 14 1 0 0 0 0 9 16 1 0 0 0 0 9 27 1 0 0 0 0 10 15 2 0 0 0 0 10 35 1 0 0 0 0 11 16 1 0 0 0 0 12 19 2 0 0 0 0 12 23 1 0 0 0 0 13 19 1 0 0 0 0 13 24 1 0 0 0 0 14 18 2 0 0 0 0 14 25 1 0 0 0 0 15 18 1 0 0 0 0 15 26 1 0 0 0 0 16 30 1 0 0 0 0 17 20 1 0 0 0 0 17 21 1 0 0 0 0 17 29 2 0 0 0 0 18 33 1 0 0 0 0 19 34 1 0 0 0 0 20 22 1 6 0 0 0 20 31 1 0 0 0 0 21 28 1 0 0 0 0 21 32 2 0 0 0 0 22 8 1 6 0 0 0 22 35 1 0 0 0 0 22 36 1 0 0 0 0 29 36 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	758.84
Volume:	516.6
LogP:	3.246
LogD:	1.905
LogS:	-2.858
# Rotatable Bonds:	11
TPSA:	127.38
# H-Bond Aceptor:	10
# H-Bond Donor:	4
# Rings:	3
# Heavy Atoms:	14

MedChem Properties

QED Drug-Likeness Score:	0.21
Synthetic Accessibility Score:	5.107
Fsp3:	0.455
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:	-5.289
MDCK Permeability:	1.702096597000491e-05
Pgp-inhibitor:	0.201
Pgp-substrate:	0.004
Human Intestinal Absorption (HIA):	0.678
20% Bioavailability (F20%):	0.992
30% Bioavailability (F30%):	0.998

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.615
Plasma Protein Binding (PPB):	93.63542938232422%
Volume Distribution (VD):	1.227
Pgp-substrate:	11.150873184204102%

ADMET: Metabolism

CYP1A2-inhibitor:	0.267
CYP1A2-substrate:	0.575
CYP2C19-inhibitor:	0.494
CYP2C19-substrate:	0.619
CYP2C9-inhibitor:	0.215
CYP2C9-substrate:	0.075
CYP2D6-inhibitor:	0.131
CYP2D6-substrate:	0.154
CYP3A4-inhibitor:	0.918
CYP3A4-substrate:	0.844

ADMET: Excretion

Clearance (CL):	1.692
Half-life (T1/2):	0.216

ADMET: Toxicity

hERG Blockers:	0.398
Human Hepatotoxicity (H-HT):	0.255
Drug-inuced Liver Injury (DILI):	0.32
AMES Toxicity:	0.043
Rat Oral Acute Toxicity:	0.74
Maximum Recommended Daily Dose:	0.951
Skin Sensitization:	0.244
Carcinogencity:	0.668
Eye Corrosion:	0.003
Eye Irritation:	0.004
Respiratory Toxicity:	0.949

Download Data

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

Natural Product: NPC475843

Natural Product ID:	NPC475843
*Common Name:**	Psammaplysin C
IUPAC Name:	(4S,5S)-7,9-dibromo-N-[3-[2,6-dibromo-4-[1-hydroxy-2-(methylamino)ethyl]phenoxy]propyl]-4-hydroxy-8-methoxy-1,11-dioxa-2-azaspiro[4.6]undeca-2,7,9-triene-3-carboxamide
Synonyms:	Psammaplysin C
Standard InCHIKey:	KHWOJHLZIWAPIG-OIGSQQCRSA-N
Standard InCHI:	InChI=1S/C22H25Br4N3O7/c1-27-9-16(30)11-6-12(23)19(13(24)7-11)34-5-3-4-28-21(32)17-20(31)22(36-29-17)8-14(25)18(33-2)15(26)10-35-22/h6-7,10,16,20,27,30-31H,3-5,8-9H2,1-2H3,(H,28,32)/t16?,20-,22-/m0/s1
SMILES:	CNCC(C1=CC(=C(C(=C1)Br)OCCCNC(=O)C2=NOC3(C2O)CC(=C(C(=CO3)Br)OC)Br)Br)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL517220
PubChem CID:	44584721
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	=	3.0	ug.mL-1	PMID[468105]

☑ 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 NPC475843 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	252
0.1-0.2	1472
0.2-0.3	8178
0.3-0.4	10466
0.4-0.5	14277
0.5-0.6	7656
0.6-0.7	345
0.7-0.8	25
0.8-0.85	4
0.85-0.9	14
0.9-0.95	2
0.95-1	6

Similarity Score	Similarity Level	Natural Product ID
0.9942	High Similarity	NPC474678
0.9942	High Similarity	NPC471338
0.9607	High Similarity	NPC471337
0.9593	High Similarity	NPC8093
0.9593	High Similarity	NPC121571
0.9348	High Similarity	NPC470746
0.9348	High Similarity	NPC471336
0.9005	High Similarity	NPC471335
0.8967	High Similarity	NPC123140
0.8953	High Similarity	NPC477255
0.8827	High Similarity	NPC77435
0.8827	High Similarity	NPC259071
0.8715	High Similarity	NPC477254
0.8641	High Similarity	NPC227953
0.8639	High Similarity	NPC471339
0.8495	Intermediate Similarity	NPC202866
0.837	Intermediate Similarity	NPC174607
0.8324	Intermediate Similarity	NPC147847
0.7989	Intermediate Similarity	NPC469711
0.7753	Intermediate Similarity	NPC156311
0.75	Intermediate Similarity	NPC474673
0.7459	Intermediate Similarity	NPC233926
0.743	Intermediate Similarity	NPC258222
0.7389	Intermediate Similarity	NPC47672
0.7356	Intermediate Similarity	NPC128877
0.733	Intermediate Similarity	NPC308571
0.7278	Intermediate Similarity	NPC76412
0.7238	Intermediate Similarity	NPC109968
0.7222	Intermediate Similarity	NPC248822
0.7121	Intermediate Similarity	NPC246591
0.7108	Intermediate Similarity	NPC473450
0.7095	Intermediate Similarity	NPC78530
0.7071	Intermediate Similarity	NPC475658
0.7071	Intermediate Similarity	NPC473892
0.7035	Intermediate Similarity	NPC141405
0.7035	Intermediate Similarity	NPC473409
0.7035	Intermediate Similarity	NPC82741
0.701	Intermediate Similarity	NPC143450
0.7	Intermediate Similarity	NPC135349
0.6989	Remote Similarity	NPC470471
0.6985	Remote Similarity	NPC471591
0.6983	Remote Similarity	NPC474128
0.6978	Remote Similarity	NPC71629
0.6946	Remote Similarity	NPC80514
0.6935	Remote Similarity	NPC49172
0.6931	Remote Similarity	NPC102245
0.6914	Remote Similarity	NPC247018
0.6914	Remote Similarity	NPC307123
0.6914	Remote Similarity	NPC97870
0.691	Remote Similarity	NPC470470
0.6906	Remote Similarity	NPC470472
0.69	Remote Similarity	NPC96275
0.6885	Remote Similarity	NPC296085
0.6863	Remote Similarity	NPC469721
0.6859	Remote Similarity	NPC469479
0.6847	Remote Similarity	NPC64066
0.6839	Remote Similarity	NPC471568
0.6839	Remote Similarity	NPC196091
0.6839	Remote Similarity	NPC473693
0.6832	Remote Similarity	NPC283207
0.6814	Remote Similarity	NPC65714
0.6802	Remote Similarity	NPC272463
0.6791	Remote Similarity	NPC73132
0.6791	Remote Similarity	NPC471235
0.6791	Remote Similarity	NPC235033
0.6763	Remote Similarity	NPC110131
0.6716	Remote Similarity	NPC299806
0.6715	Remote Similarity	NPC469731
0.6715	Remote Similarity	NPC471592
0.6713	Remote Similarity	NPC326027
0.6703	Remote Similarity	NPC204546
0.6698	Remote Similarity	NPC326333
0.6667	Remote Similarity	NPC469979
0.6667	Remote Similarity	NPC226001
0.6667	Remote Similarity	NPC230539
0.665	Remote Similarity	NPC80337
0.6633	Remote Similarity	NPC126128
0.6633	Remote Similarity	NPC207819
0.6633	Remote Similarity	NPC298981
0.6633	Remote Similarity	NPC110454
0.6633	Remote Similarity	NPC473462
0.6615	Remote Similarity	NPC186617
0.6603	Remote Similarity	NPC477552
0.6603	Remote Similarity	NPC477550
0.6593	Remote Similarity	NPC40321
0.6578	Remote Similarity	NPC20755
0.6578	Remote Similarity	NPC324081
0.6571	Remote Similarity	NPC320242
0.6571	Remote Similarity	NPC123859
0.6567	Remote Similarity	NPC475396
0.6552	Remote Similarity	NPC315542
0.654	Remote Similarity	NPC242728
0.654	Remote Similarity	NPC477551
0.6536	Remote Similarity	NPC474753
0.6535	Remote Similarity	NPC74618
0.6535	Remote Similarity	NPC301941
0.6535	Remote Similarity	NPC214188
0.6533	Remote Similarity	NPC225130
0.6531	Remote Similarity	NPC469505
0.6524	Remote Similarity	NPC323662
0.652	Remote Similarity	NPC276120
0.6509	Remote Similarity	NPC214368
0.6482	Remote Similarity	NPC471165
0.648	Remote Similarity	NPC475735
0.648	Remote Similarity	NPC473724
0.648	Remote Similarity	NPC209463
0.6476	Remote Similarity	NPC144314
0.6468	Remote Similarity	NPC475421
0.6467	Remote Similarity	NPC470709
0.6458	Remote Similarity	NPC56635
0.6448	Remote Similarity	NPC213471
0.6445	Remote Similarity	NPC50548
0.6444	Remote Similarity	NPC470392
0.6436	Remote Similarity	NPC290534
0.6429	Remote Similarity	NPC254700
0.6429	Remote Similarity	NPC149962
0.6425	Remote Similarity	NPC474091
0.6425	Remote Similarity	NPC474087
0.6419	Remote Similarity	NPC81845
0.6411	Remote Similarity	NPC328763
0.6408	Remote Similarity	NPC144823
0.6396	Remote Similarity	NPC473502
0.6394	Remote Similarity	NPC477526
0.639	Remote Similarity	NPC138083
0.6384	Remote Similarity	NPC141739
0.6384	Remote Similarity	NPC136112
0.6383	Remote Similarity	NPC313414
0.6382	Remote Similarity	NPC89831
0.6378	Remote Similarity	NPC472923
0.6378	Remote Similarity	NPC63931
0.6378	Remote Similarity	NPC158900
0.6373	Remote Similarity	NPC470112
0.6373	Remote Similarity	NPC470903
0.6373	Remote Similarity	NPC167763
0.6359	Remote Similarity	NPC197045
0.6355	Remote Similarity	NPC156055
0.6354	Remote Similarity	NPC476268
0.6349	Remote Similarity	NPC132771
0.634	Remote Similarity	NPC319320
0.634	Remote Similarity	NPC287757
0.6329	Remote Similarity	NPC94862
0.6326	Remote Similarity	NPC311357
0.6319	Remote Similarity	NPC163810
0.6319	Remote Similarity	NPC132308
0.6319	Remote Similarity	NPC169766
0.6307	Remote Similarity	NPC116562
0.6304	Remote Similarity	NPC470248
0.6304	Remote Similarity	NPC470249
0.6303	Remote Similarity	NPC59827
0.6303	Remote Similarity	NPC184933
0.6301	Remote Similarity	NPC477160
0.63	Remote Similarity	NPC328494
0.629	Remote Similarity	NPC251439
0.6284	Remote Similarity	NPC303993
0.6281	Remote Similarity	NPC280022
0.6275	Remote Similarity	NPC32064
0.6273	Remote Similarity	NPC295795
0.6269	Remote Similarity	NPC244509
0.6269	Remote Similarity	NPC123011
0.6269	Remote Similarity	NPC273755
0.6269	Remote Similarity	NPC256689
0.6268	Remote Similarity	NPC29531
0.6267	Remote Similarity	NPC14339
0.625	Remote Similarity	NPC46009
0.625	Remote Similarity	NPC196708
0.6238	Remote Similarity	NPC473407
0.6238	Remote Similarity	NPC26108
0.6238	Remote Similarity	NPC164608
0.6238	Remote Similarity	NPC473378
0.623	Remote Similarity	NPC243404
0.6224	Remote Similarity	NPC37205
0.6224	Remote Similarity	NPC476194
0.6224	Remote Similarity	NPC160931
0.622	Remote Similarity	NPC470951
0.6216	Remote Similarity	NPC473052
0.6216	Remote Similarity	NPC473055
0.6215	Remote Similarity	NPC477527
0.6209	Remote Similarity	NPC11449
0.6207	Remote Similarity	NPC477115
0.6207	Remote Similarity	NPC50016
0.6205	Remote Similarity	NPC67658
0.6203	Remote Similarity	NPC81137
0.6203	Remote Similarity	NPC469360
0.619	Remote Similarity	NPC174122
0.619	Remote Similarity	NPC64140
0.619	Remote Similarity	NPC63628
0.619	Remote Similarity	NPC178466
0.619	Remote Similarity	NPC81026
0.6188	Remote Similarity	NPC248670
0.6186	Remote Similarity	NPC470710
0.6186	Remote Similarity	NPC476741
0.6183	Remote Similarity	NPC322526
0.6173	Remote Similarity	NPC244336
0.6172	Remote Similarity	NPC4910
0.6171	Remote Similarity	NPC92235
0.6169	Remote Similarity	NPC475123
0.6169	Remote Similarity	NPC475204
0.6168	Remote Similarity	NPC281629
0.6162	Remote Similarity	NPC6570
0.6162	Remote Similarity	NPC235633

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 NPC475843 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	152
0.1-0.2	556
0.2-0.3	1499
0.3-0.4	2565
0.4-0.5	2916
0.5-0.6	1327
0.6-0.7	135
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
0.6966	Remote Similarity	NPD2240	Approved
0.6966	Remote Similarity	NPD2239	Approved
0.6914	Remote Similarity	NPD1423	Approved
0.6848	Remote Similarity	NPD3536	Discontinued
0.6818	Remote Similarity	NPD5192	Clinical (unspecified phase)
0.68	Remote Similarity	NPD3180	Approved
0.68	Remote Similarity	NPD3179	Approved
0.6758	Remote Similarity	NPD2976	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD7608	Discontinued
0.6649	Remote Similarity	NPD3687	Approved
0.6649	Remote Similarity	NPD3686	Approved
0.6611	Remote Similarity	NPD3052	Approved
0.6611	Remote Similarity	NPD3054	Approved
0.6596	Remote Similarity	NPD7131	Phase 3
0.6593	Remote Similarity	NPD3175	Clinical (unspecified phase)
0.6571	Remote Similarity	NPD1820	Approved
0.6571	Remote Similarity	NPD1818	Approved
0.6571	Remote Similarity	NPD1819	Approved
0.6571	Remote Similarity	NPD1817	Approved
0.6546	Remote Similarity	NPD8031	Discontinued
0.6545	Remote Similarity	NPD2541	Clinical (unspecified phase)
0.6531	Remote Similarity	NPD7485	Phase 3
0.6531	Remote Similarity	NPD7484	Phase 3
0.652	Remote Similarity	NPD3153	Approved
0.652	Remote Similarity	NPD3154	Approved
0.6517	Remote Similarity	NPD3165	Approved
0.6517	Remote Similarity	NPD3167	Approved
0.6517	Remote Similarity	NPD3164	Approved
0.6517	Remote Similarity	NPD9718	Approved
0.6517	Remote Similarity	NPD3166	Approved
0.6515	Remote Similarity	NPD3451	Clinical (unspecified phase)
0.6489	Remote Similarity	NPD3985	Discontinued
0.6458	Remote Similarity	NPD6677	Suspended
0.6458	Remote Similarity	NPD6072	Discontinued
0.6442	Remote Similarity	NPD5165	Clinical (unspecified phase)
0.6429	Remote Similarity	NPD6315	Phase 2
0.6417	Remote Similarity	NPD2677	Approved
0.6413	Remote Similarity	NPD1725	Approved
0.6404	Remote Similarity	NPD7038	Approved
0.6404	Remote Similarity	NPD7039	Approved
0.6402	Remote Similarity	NPD4661	Approved
0.6402	Remote Similarity	NPD3158	Phase 1
0.6402	Remote Similarity	NPD5348	Clinical (unspecified phase)
0.6402	Remote Similarity	NPD3157	Approved
0.6402	Remote Similarity	NPD4662	Approved
0.6398	Remote Similarity	NPD4162	Approved
0.6396	Remote Similarity	NPD4666	Phase 3
0.6392	Remote Similarity	NPD5773	Approved
0.6392	Remote Similarity	NPD5772	Approved
0.6392	Remote Similarity	NPD3465	Clinical (unspecified phase)
0.6389	Remote Similarity	NPD3056	Clinical (unspecified phase)
0.6384	Remote Similarity	NPD1770	Clinical (unspecified phase)
0.6384	Remote Similarity	NPD1794	Approved
0.6368	Remote Similarity	NPD1975	Clinical (unspecified phase)
0.6359	Remote Similarity	NPD7318	Phase 3
0.6354	Remote Similarity	NPD3162	Approved
0.6354	Remote Similarity	NPD3163	Approved
0.635	Remote Similarity	NPD4575	Clinical (unspecified phase)
0.6345	Remote Similarity	NPD5709	Phase 3
0.634	Remote Similarity	NPD4018	Clinical (unspecified phase)
0.6338	Remote Similarity	NPD7810	Phase 3
0.6338	Remote Similarity	NPD7811	Phase 3
0.6333	Remote Similarity	NPD4466	Phase 1
0.6329	Remote Similarity	NPD3863	Clinical (unspecified phase)
0.6316	Remote Similarity	NPD6419	Discontinued
0.6313	Remote Similarity	NPD2042	Clinical (unspecified phase)
0.6313	Remote Similarity	NPD2041	Clinical (unspecified phase)
0.631	Remote Similarity	NPD2458	Approved
0.631	Remote Similarity	NPD2460	Phase 3
0.631	Remote Similarity	NPD2459	Approved
0.631	Remote Similarity	NPD3060	Approved
0.6308	Remote Similarity	NPD7972	Discontinued
0.6308	Remote Similarity	NPD2978	Approved
0.6308	Remote Similarity	NPD2977	Approved
0.6305	Remote Similarity	NPD5557	Phase 1
0.63	Remote Similarity	NPD2215	Approved
0.63	Remote Similarity	NPD2216	Approved
0.6288	Remote Similarity	NPD8058	Clinical (unspecified phase)
0.6288	Remote Similarity	NPD8059	Phase 3
0.6287	Remote Similarity	NPD6620	Discovery
0.6283	Remote Similarity	NPD2183	Approved
0.6283	Remote Similarity	NPD2184	Approved
0.6269	Remote Similarity	NPD2651	Approved
0.6269	Remote Similarity	NPD2649	Approved
0.6263	Remote Similarity	NPD1774	Approved
0.6256	Remote Similarity	NPD5355	Approved
0.6256	Remote Similarity	NPD7317	Phase 3
0.6256	Remote Similarity	NPD5356	Approved
0.6244	Remote Similarity	NPD1298	Discontinued
0.6243	Remote Similarity	NPD5163	Phase 2
0.6238	Remote Similarity	NPD5525	Clinical (unspecified phase)
0.6231	Remote Similarity	NPD2904	Discontinued
0.623	Remote Similarity	NPD3597	Clinical (unspecified phase)
0.623	Remote Similarity	NPD2874	Phase 2
0.6222	Remote Similarity	NPD2250	Discontinued
0.6219	Remote Similarity	NPD5137	Approved
0.6211	Remote Similarity	NPD3281	Clinical (unspecified phase)
0.6207	Remote Similarity	NPD3909	Discontinued
0.6205	Remote Similarity	NPD7118	Clinical (unspecified phase)
0.6198	Remote Similarity	NPD7526	Approved
0.6198	Remote Similarity	NPD52	Approved
0.6198	Remote Similarity	NPD7527	Clinical (unspecified phase)
0.619	Remote Similarity	NPD6377	Clinical (unspecified phase)
0.6176	Remote Similarity	NPD6042	Phase 2
0.6176	Remote Similarity	NPD42	Phase 2
0.6175	Remote Similarity	NPD5745	Approved
0.6172	Remote Similarity	NPD3857	Clinical (unspecified phase)
0.617	Remote Similarity	NPD7596	Clinical (unspecified phase)
0.617	Remote Similarity	NPD7153	Discontinued
0.6158	Remote Similarity	NPD5605	Phase 2
0.6154	Remote Similarity	NPD3136	Phase 2
0.6154	Remote Similarity	NPD6853	Approved
0.6154	Remote Similarity	NPD6851	Approved
0.615	Remote Similarity	NPD7256	Discontinued
0.6146	Remote Similarity	NPD3146	Approved
0.6146	Remote Similarity	NPD3688	Clinical (unspecified phase)
0.6142	Remote Similarity	NPD6668	Clinical (unspecified phase)
0.6138	Remote Similarity	NPD5061	Approved
0.6138	Remote Similarity	NPD4236	Phase 3
0.6138	Remote Similarity	NPD5062	Approved
0.6138	Remote Similarity	NPD4237	Approved
0.6135	Remote Similarity	NPD3936	Clinical (unspecified phase)
0.6134	Remote Similarity	NPD4124	Clinical (unspecified phase)
0.6134	Remote Similarity	NPD4210	Discontinued
0.6127	Remote Similarity	NPD2163	Approved
0.6126	Remote Similarity	NPD3122	Phase 3
0.6126	Remote Similarity	NPD5295	Discontinued
0.6117	Remote Similarity	NPD7978	Discontinued
0.6117	Remote Similarity	NPD6297	Approved
0.6117	Remote Similarity	NPD3656	Approved
0.6114	Remote Similarity	NPD4258	Approved
0.6114	Remote Similarity	NPD4186	Clinical (unspecified phase)
0.6114	Remote Similarity	NPD2676	Approved
0.6114	Remote Similarity	NPD2675	Approved
0.6114	Remote Similarity	NPD4259	Approved
0.6114	Remote Similarity	NPD2186	Approved
0.6114	Remote Similarity	NPD7613	Discontinued
0.6101	Remote Similarity	NPD6863	Phase 2
0.6096	Remote Similarity	NPD2156	Approved
0.6096	Remote Similarity	NPD2154	Approved
0.6096	Remote Similarity	NPD2155	Approved
0.6094	Remote Similarity	NPD6087	Phase 1
0.6089	Remote Similarity	NPD3676	Clinical (unspecified phase)
0.6087	Remote Similarity	NPD1726	Clinical (unspecified phase)
0.6087	Remote Similarity	NPD2245	Discovery
0.6085	Remote Similarity	NPD6681	Discovery
0.6085	Remote Similarity	NPD3808	Clinical (unspecified phase)
0.6075	Remote Similarity	NPD1772	Clinical (unspecified phase)
0.6073	Remote Similarity	NPD5160	Discontinued
0.6071	Remote Similarity	NPD7827	Phase 1
0.6066	Remote Similarity	NPD5746	Approved
0.6064	Remote Similarity	NPD2161	Phase 2
0.6062	Remote Similarity	NPD681	Clinical (unspecified phase)
0.6058	Remote Similarity	NPD7132	Clinical (unspecified phase)
0.6057	Remote Similarity	NPD856	Approved
0.6057	Remote Similarity	NPD16	Approved
0.6055	Remote Similarity	NPD7476	Discontinued
0.6044	Remote Similarity	NPD5266	Clinical (unspecified phase)
0.6034	Remote Similarity	NPD2561	Approved
0.6034	Remote Similarity	NPD2562	Approved
0.6032	Remote Similarity	NPD1375	Discontinued
0.6031	Remote Similarity	NPD5261	Clinical (unspecified phase)
0.6031	Remote Similarity	NPD6390	Discontinued
0.603	Remote Similarity	NPD3560	Approved
0.603	Remote Similarity	NPD3558	Approved
0.603	Remote Similarity	NPD3559	Clinical (unspecified phase)
0.603	Remote Similarity	NPD3557	Approved
0.603	Remote Similarity	NPD3556	Approved
0.6011	Remote Similarity	NPD2614	Approved
0.6009	Remote Similarity	NPD6519	Phase 2
0.6	Remote Similarity	NPD3366	Approved
0.6	Remote Similarity	NPD3685	Discontinued
0.6	Remote Similarity	NPD3532	Approved
0.6	Remote Similarity	NPD3530	Approved
0.6	Remote Similarity	NPD5586	Clinical (unspecified phase)
0.6	Remote Similarity	NPD3531	Approved
0.5991	Remote Similarity	NPD4157	Discontinued
0.5991	Remote Similarity	NPD7584	Approved
0.5989	Remote Similarity	NPD2653	Approved
0.5981	Remote Similarity	NPD7296	Approved
0.5981	Remote Similarity	NPD4419	Clinical (unspecified phase)
0.5981	Remote Similarity	NPD2802	Phase 3
0.598	Remote Similarity	NPD2388	Discontinued
0.5979	Remote Similarity	NPD6032	Approved
0.5979	Remote Similarity	NPD4123	Phase 3
0.5979	Remote Similarity	NPD1771	Clinical (unspecified phase)
0.5979	Remote Similarity	NPD5712	Approved
0.5971	Remote Similarity	NPD5940	Clinical (unspecified phase)
0.597	Remote Similarity	NPD8070	Approved
0.5967	Remote Similarity	NPD196	Phase 1
0.5966	Remote Similarity	NPD317	Approved
0.5966	Remote Similarity	NPD318	Approved
0.5963	Remote Similarity	NPD7565	Approved
0.5962	Remote Similarity	NPD2843	Phase 2
0.5962	Remote Similarity	NPD2845	Phase 2
0.5959	Remote Similarity	NPD6666	Approved
0.5959	Remote Similarity	NPD6667	Approved
0.5957	Remote Similarity	NPD3554	Approved
0.5957	Remote Similarity	NPD3553	Approved
0.5957	Remote Similarity	NPD3555	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