NPASS Compound

Structure

NPC471339 OpenBabel07101718192D 43 46 0 0 1 0 0 0 0 0999 V2000 -4.4234 1.4266 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0981 -3.0388 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.2942 -1.0388 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2321 -2.5388 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.1603 -1.5388 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9641 -2.5388 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.5622 -1.0388 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.4282 -2.5388 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 10.3923 -4.0777 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9839 -0.1786 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.8923 -1.5388 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9192 1.8001 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.4282 -1.5388 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.8923 -2.5388 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.6962 -1.5388 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.5622 -3.0388 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7370 0.4794 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8831 2.0662 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.3923 -4.0777 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 10.7013 -3.1266 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5000 -1.5388 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.0833 -3.1266 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6921 1.4784 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.6962 -2.5388 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3090 -0.9511 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.5000 -2.5388 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0000 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.8301 -1.0388 0.0000 Br 0 0 0 0 0 0 0 0 0 0 0 0 5.5622 -4.0388 0.0000 Br 0 0 0 0 0 0 0 0 0 0 0 0 -3.6565 0.0864 0.0000 Br 0 0 0 0 0 0 0 0 0 0 0 0 -2.0617 3.0501 0.0000 Br 0 0 0 0 0 0 0 0 0 0 0 0 8.8045 -4.8867 0.0000 Cl 0 0 0 0 0 0 0 0 0 0 0 0 9.0263 -1.0388 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 0.3660 -3.0388 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 0.3090 -0.9511 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 11.6524 -2.8176 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 8.1322 -2.8176 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.2601 -1.2601 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.3660 -3.0388 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.5727 1.9522 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.8301 -3.0388 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.5261 0.8806 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 40 1 0 0 0 0 2 4 1 0 0 0 0 2 6 1 0 0 0 0 3 5 1 0 0 0 0 3 13 1 0 0 0 0 4 34 1 0 0 0 0 5 33 1 0 0 0 0 6 41 1 0 0 0 0 7 13 2 0 0 0 0 7 15 1 0 0 0 0 8 13 1 0 0 0 0 8 16 2 0 0 0 0 9 19 1 0 0 0 0 9 20 1 0 0 0 0 10 17 1 0 0 0 0 11 14 2 0 0 0 0 11 33 1 0 0 0 0 12 18 2 0 0 0 0 12 42 1 0 0 0 0 14 20 1 0 0 0 0 14 22 1 0 0 0 0 15 24 2 0 0 0 0 15 28 1 0 0 0 0 16 24 1 0 0 0 0 16 29 1 0 0 0 0 17 23 2 0 0 0 0 17 30 1 0 0 0 0 18 23 1 0 0 0 0 18 31 1 0 0 0 0 19 22 1 0 0 0 0 19 32 1 0 0 0 0 20 36 2 0 0 0 0 21 25 1 0 0 0 0 21 26 1 0 0 0 0 21 35 2 0 0 0 0 22 37 2 0 0 0 0 23 40 1 0 0 0 0 24 41 1 0 0 0 0 25 27 1 6 0 0 0 25 38 1 0 0 0 0 26 34 1 0 0 0 0 26 39 2 0 0 0 0 27 10 1 6 0 0 0 27 42 1 0 0 0 0 27 43 1 0 0 0 0 35 43 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	870.81
Volume:	610.615
LogP:	4.009
LogD:	1.468
LogS:	-2.812
# Rotatable Bonds:	12
TPSA:	141.62
# H-Bond Aceptor:	11
# H-Bond Donor:	2
# Rings:	4
# Heavy Atoms:	16

MedChem Properties

QED Drug-Likeness Score:	0.142
Synthetic Accessibility Score:	5.671
Fsp3:	0.444
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	2
Golden Triangle Rule:	Rejected
Chelating Alert:	2
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.916
MDCK Permeability:	1.5425021047121845e-05
Pgp-inhibitor:	0.946
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.647
20% Bioavailability (F20%):	0.995
30% Bioavailability (F30%):	0.998

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.046
Plasma Protein Binding (PPB):	96.94618225097656%
Volume Distribution (VD):	0.992
Pgp-substrate:	3.712120294570923%

ADMET: Metabolism

CYP1A2-inhibitor:	0.156
CYP1A2-substrate:	0.627
CYP2C19-inhibitor:	0.781
CYP2C19-substrate:	0.726
CYP2C9-inhibitor:	0.854
CYP2C9-substrate:	0.067
CYP2D6-inhibitor:	0.054
CYP2D6-substrate:	0.18
CYP3A4-inhibitor:	0.974
CYP3A4-substrate:	0.886

ADMET: Excretion

Clearance (CL):	1.49
Half-life (T1/2):	0.177

ADMET: Toxicity

hERG Blockers:	0.16
Human Hepatotoxicity (H-HT):	0.335
Drug-inuced Liver Injury (DILI):	0.894
AMES Toxicity:	0.032
Rat Oral Acute Toxicity:	0.989
Maximum Recommended Daily Dose:	0.934
Skin Sensitization:	0.435
Carcinogencity:	0.55
Eye Corrosion:	0.003
Eye Irritation:	0.005
Respiratory Toxicity:	0.972

Download Data

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

Natural Product: NPC471339

Natural Product ID:	NPC471339
*Common Name:**	Psammaplysine X
IUPAC Name:	(4S,5S)-7,9-dibromo-N-[3-[2,6-dibromo-4-[2-[[(Z)-(3-chloro-2,5-dioxocyclopentylidene)methyl]amino]ethyl]phenoxy]propyl]-4-hydroxy-8-methoxy-1,11-dioxa-2-azaspiro[4.6]undeca-2,7,9-triene-3-carboxamide
Synonyms:
Standard InCHIKey:	YNMCLVMISHJRBL-YJGHPRERSA-N
Standard InCHI:	InChI=1S/C27H26Br4ClN3O8/c1-40-23-17(30)10-27(42-12-18(23)31)25(38)21(35-43-27)26(39)34-4-2-6-41-24-15(28)7-13(8-16(24)29)3-5-33-11-14-20(36)9-19(32)22(14)37/h7-8,11-12,19,25,33,38H,2-6,9-10H2,1H3,(H,34,39)/b14-11-/t19?,25-,27-/m0/s1
SMILES:	COC1=C(Br)C[C@]2(OC=C1Br)ON=C([C@@H]2O)C(=O)NCCCOc1c(Br)cc(cc1Br)CCN/C=C1/C(=O)CC(C1=O)Cl
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2419320
PubChem CID:	73349161
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0002279] Benzene and substituted derivatives [CHEMONTID:0000186] Phenethylamines

*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
NPO32567	suberea sp.	Species	Aplysinellidae	Eukaryota	n.a.	n.a.	n.a.	PMID[11473442]
NPO32567	suberea sp.	Species	Aplysinellidae	Eukaryota	n.a.	n.a.	n.a.	PMID[23964644]

☑ 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
GI50	6

Activity Type	# Activity
Cell Line	6

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT370	Cell Line	NCI-H23	Homo sapiens	GI50	=	6400.0	nM	PMID[518026]
NPT2477	Cell Line	NUGC-3	Homo sapiens	GI50	=	3500.0	nM	PMID[518026]
NPT82	Cell Line	MDA-MB-231	Homo sapiens	GI50	=	1200.0	nM	PMID[518026]
NPT369	Cell Line	ACHN	Homo sapiens	GI50	=	3300.0	nM	PMID[518026]
NPT306	Cell Line	PC-3	Homo sapiens	GI50	=	2300.0	nM	PMID[518026]
NPT148	Cell Line	HCT-15	Homo sapiens	GI50	=	3300.0	nM	PMID[518026]

☑ 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 NPC471339 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	262
0.1-0.2	1848
0.2-0.3	10290
0.3-0.4	9523
0.4-0.5	18903
0.5-0.6	1738
0.6-0.7	105
0.7-0.8	15
0.8-0.85	3
0.85-0.9	7
0.9-0.95	1
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9634	High Similarity	NPC471335
0.9305	High Similarity	NPC123140
0.8969	High Similarity	NPC471336
0.8969	High Similarity	NPC470746
0.8967	High Similarity	NPC8093
0.8967	High Similarity	NPC121571
0.8684	High Similarity	NPC474678
0.8684	High Similarity	NPC471338
0.8639	High Similarity	NPC475843
0.8513	High Similarity	NPC471337
0.837	Intermediate Similarity	NPC477255
0.8177	Intermediate Similarity	NPC259071
0.8177	Intermediate Similarity	NPC77435
0.8168	Intermediate Similarity	NPC477254
0.8071	Intermediate Similarity	NPC202866
0.7929	Intermediate Similarity	NPC227953
0.7766	Intermediate Similarity	NPC174607
0.7727	Intermediate Similarity	NPC147847
0.7173	Intermediate Similarity	NPC156311
0.6927	Remote Similarity	NPC469711
0.6882	Remote Similarity	NPC128877
0.6875	Remote Similarity	NPC258222
0.6862	Remote Similarity	NPC308571
0.6847	Remote Similarity	NPC143450
0.6753	Remote Similarity	NPC47672
0.6736	Remote Similarity	NPC76412
0.6735	Remote Similarity	NPC233926
0.6719	Remote Similarity	NPC71629
0.6701	Remote Similarity	NPC109968
0.6651	Remote Similarity	NPC248822
0.6632	Remote Similarity	NPC296085
0.6562	Remote Similarity	NPC78530
0.6504	Remote Similarity	NPC326027
0.6489	Remote Similarity	NPC326333
0.6484	Remote Similarity	NPC473450
0.6477	Remote Similarity	NPC135349
0.6474	Remote Similarity	NPC474673
0.6455	Remote Similarity	NPC470471
0.6422	Remote Similarity	NPC209463
0.6402	Remote Similarity	NPC246591
0.6392	Remote Similarity	NPC470472
0.6387	Remote Similarity	NPC470470
0.6373	Remote Similarity	NPC474128
0.6359	Remote Similarity	NPC473693
0.6359	Remote Similarity	NPC272463
0.6359	Remote Similarity	NPC471568
0.6351	Remote Similarity	NPC475396
0.633	Remote Similarity	NPC80514
0.6324	Remote Similarity	NPC110131
0.6318	Remote Similarity	NPC323662
0.6313	Remote Similarity	NPC102245
0.628	Remote Similarity	NPC196091
0.6279	Remote Similarity	NPC471591
0.6279	Remote Similarity	NPC475658
0.6279	Remote Similarity	NPC473892
0.6262	Remote Similarity	NPC299806
0.625	Remote Similarity	NPC82741
0.625	Remote Similarity	NPC141405
0.625	Remote Similarity	NPC473409
0.6244	Remote Similarity	NPC301941
0.6244	Remote Similarity	NPC214188
0.6244	Remote Similarity	NPC74618
0.6239	Remote Similarity	NPC64066
0.6232	Remote Similarity	NPC186617
0.6211	Remote Similarity	NPC247018
0.6211	Remote Similarity	NPC307123
0.6211	Remote Similarity	NPC97870
0.621	Remote Similarity	NPC65714
0.621	Remote Similarity	NPC328763
0.6209	Remote Similarity	NPC469979
0.6209	Remote Similarity	NPC226001
0.6204	Remote Similarity	NPC96275
0.6199	Remote Similarity	NPC469731
0.6179	Remote Similarity	NPC207819
0.6179	Remote Similarity	NPC298981
0.6179	Remote Similarity	NPC473462
0.6179	Remote Similarity	NPC126128
0.6179	Remote Similarity	NPC110454
0.6157	Remote Similarity	NPC49172
0.615	Remote Similarity	NPC81845
0.615	Remote Similarity	NPC290534
0.6135	Remote Similarity	NPC469479
0.6134	Remote Similarity	NPC213471
0.613	Remote Similarity	NPC92235
0.6129	Remote Similarity	NPC144823
0.6126	Remote Similarity	NPC471592
0.6109	Remote Similarity	NPC469721
0.61	Remote Similarity	NPC324081
0.6094	Remote Similarity	NPC67658
0.6087	Remote Similarity	NPC295795
0.6085	Remote Similarity	NPC225130
0.6073	Remote Similarity	NPC230539
0.6073	Remote Similarity	NPC283207
0.6059	Remote Similarity	NPC235033
0.6059	Remote Similarity	NPC471235
0.6059	Remote Similarity	NPC73132
0.6055	Remote Similarity	NPC80337
0.6041	Remote Similarity	NPC204546
0.6028	Remote Similarity	NPC475421
0.602	Remote Similarity	NPC20755
0.6019	Remote Similarity	NPC167763
0.6019	Remote Similarity	NPC470112
0.6019	Remote Similarity	NPC470903
0.6018	Remote Similarity	NPC214368
0.601	Remote Similarity	NPC132308
0.6009	Remote Similarity	NPC14339
0.6008	Remote Similarity	NPC243633
0.6008	Remote Similarity	NPC175150
0.6	Remote Similarity	NPC469505
0.5981	Remote Similarity	NPC254700
0.598	Remote Similarity	NPC470710
0.5979	Remote Similarity	NPC470441
0.5979	Remote Similarity	NPC303993
0.5963	Remote Similarity	NPC315542
0.5959	Remote Similarity	NPC474753
0.5957	Remote Similarity	NPC219350
0.5957	Remote Similarity	NPC194699
0.5953	Remote Similarity	NPC475615
0.5949	Remote Similarity	NPC196708
0.5939	Remote Similarity	NPC40321
0.5938	Remote Similarity	NPC474087
0.5936	Remote Similarity	NPC276120
0.5933	Remote Similarity	NPC158900
0.5933	Remote Similarity	NPC472923
0.5928	Remote Similarity	NPC169766
0.5922	Remote Similarity	NPC56635
0.5907	Remote Similarity	NPC473724
0.5907	Remote Similarity	NPC475735
0.5902	Remote Similarity	NPC256689
0.5902	Remote Similarity	NPC123011
0.5895	Remote Similarity	NPC320242
0.5885	Remote Similarity	NPC67080
0.5882	Remote Similarity	NPC124626
0.5876	Remote Similarity	NPC470392
0.5859	Remote Similarity	NPC123859
0.5855	Remote Similarity	NPC277306
0.5855	Remote Similarity	NPC469442
0.5855	Remote Similarity	NPC474091
0.5847	Remote Similarity	NPC50562
0.5833	Remote Similarity	NPC242728
0.5829	Remote Similarity	NPC71205
0.5829	Remote Similarity	NPC470709
0.582	Remote Similarity	NPC116562
0.5818	Remote Similarity	NPC138083
0.5815	Remote Similarity	NPC477550
0.5815	Remote Similarity	NPC477552
0.5811	Remote Similarity	NPC470951
0.5808	Remote Similarity	NPC197045
0.5805	Remote Similarity	NPC25539
0.5802	Remote Similarity	NPC473502
0.5794	Remote Similarity	NPC89831
0.5792	Remote Similarity	NPC119569
0.5785	Remote Similarity	NPC223384
0.5782	Remote Similarity	NPC63931
0.5782	Remote Similarity	NPC293164
0.5782	Remote Similarity	NPC471394
0.5773	Remote Similarity	NPC99280
0.5767	Remote Similarity	NPC248670
0.5765	Remote Similarity	NPC163810
0.5764	Remote Similarity	NPC477551
0.5758	Remote Similarity	NPC106606
0.5758	Remote Similarity	NPC307682
0.5753	Remote Similarity	NPC28368
0.575	Remote Similarity	NPC81137
0.5747	Remote Similarity	NPC128683
0.5744	Remote Similarity	NPC11449
0.5743	Remote Similarity	NPC147137
0.5743	Remote Similarity	NPC473804
0.5742	Remote Similarity	NPC319320
0.5742	Remote Similarity	NPC287757
0.5741	Remote Similarity	NPC164608
0.5741	Remote Similarity	NPC471165
0.574	Remote Similarity	NPC471650
0.5739	Remote Similarity	NPC156055
0.5735	Remote Similarity	NPC132771
0.5729	Remote Similarity	NPC141739
0.5729	Remote Similarity	NPC471237
0.5729	Remote Similarity	NPC177967
0.5729	Remote Similarity	NPC136112
0.5727	Remote Similarity	NPC475283
0.5727	Remote Similarity	NPC152205
0.5727	Remote Similarity	NPC149962
0.5714	Remote Similarity	NPC471203
0.5708	Remote Similarity	NPC32064
0.5707	Remote Similarity	NPC235633
0.5702	Remote Similarity	NPC144314
0.5702	Remote Similarity	NPC293347
0.5702	Remote Similarity	NPC281629
0.57	Remote Similarity	NPC39431
0.5695	Remote Similarity	NPC4910
0.5695	Remote Similarity	NPC94862
0.5694	Remote Similarity	NPC90245
0.5689	Remote Similarity	NPC473378
0.5689	Remote Similarity	NPC473407
0.5686	Remote Similarity	NPC272868
0.5686	Remote Similarity	NPC270848
0.5686	Remote Similarity	NPC122599
0.5685	Remote Similarity	NPC168209
0.5684	Remote Similarity	NPC79130
0.5678	Remote Similarity	NPC470249

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 NPC471339 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	154
0.1-0.2	635
0.2-0.3	1444
0.3-0.4	2888
0.4-0.5	3368
0.5-0.6	650
0.6-0.7	11
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
0.6313	Remote Similarity	NPD5165	Clinical (unspecified phase)
0.6274	Remote Similarity	NPD5192	Clinical (unspecified phase)
0.6269	Remote Similarity	NPD2240	Approved
0.6269	Remote Similarity	NPD2239	Approved
0.6238	Remote Similarity	NPD2822	Clinical (unspecified phase)
0.6233	Remote Similarity	NPD3154	Approved
0.6233	Remote Similarity	NPD3153	Approved
0.6211	Remote Similarity	NPD1423	Approved
0.6202	Remote Similarity	NPD7608	Discontinued
0.6193	Remote Similarity	NPD5525	Clinical (unspecified phase)
0.619	Remote Similarity	NPD3366	Approved
0.6162	Remote Similarity	NPD3281	Clinical (unspecified phase)
0.6098	Remote Similarity	NPD3465	Clinical (unspecified phase)
0.6049	Remote Similarity	NPD4018	Clinical (unspecified phase)
0.602	Remote Similarity	NPD3175	Clinical (unspecified phase)
0.602	Remote Similarity	NPD4662	Approved
0.602	Remote Similarity	NPD4661	Approved
0.601	Remote Similarity	NPD8031	Discontinued
0.601	Remote Similarity	NPD2976	Clinical (unspecified phase)
0.6	Remote Similarity	NPD2541	Clinical (unspecified phase)
0.5991	Remote Similarity	NPD6863	Phase 2
0.5982	Remote Similarity	NPD3863	Clinical (unspecified phase)
0.5982	Remote Similarity	NPD3857	Clinical (unspecified phase)
0.5942	Remote Similarity	NPD7972	Discontinued
0.5941	Remote Similarity	NPD3536	Discontinued
0.5924	Remote Similarity	NPD7484	Phase 3
0.5924	Remote Similarity	NPD7485	Phase 3
0.5913	Remote Similarity	NPD7318	Phase 3
0.5909	Remote Similarity	NPD8059	Phase 3
0.5909	Remote Similarity	NPD8058	Clinical (unspecified phase)
0.5905	Remote Similarity	NPD6315	Phase 2
0.5902	Remote Similarity	NPD2651	Approved
0.5902	Remote Similarity	NPD2649	Approved
0.5895	Remote Similarity	NPD1819	Approved
0.5895	Remote Similarity	NPD1818	Approved
0.5895	Remote Similarity	NPD1817	Approved
0.5895	Remote Similarity	NPD1770	Clinical (unspecified phase)
0.5895	Remote Similarity	NPD1820	Approved
0.5882	Remote Similarity	NPD7131	Phase 3
0.5872	Remote Similarity	NPD3936	Clinical (unspecified phase)
0.5862	Remote Similarity	NPD5348	Clinical (unspecified phase)
0.5859	Remote Similarity	NPD1725	Approved
0.5856	Remote Similarity	NPD4259	Approved
0.5856	Remote Similarity	NPD4258	Approved
0.5855	Remote Similarity	NPD3164	Approved
0.5855	Remote Similarity	NPD3180	Approved
0.5855	Remote Similarity	NPD3165	Approved
0.5855	Remote Similarity	NPD3166	Approved
0.5855	Remote Similarity	NPD3179	Approved
0.5855	Remote Similarity	NPD9718	Approved
0.5855	Remote Similarity	NPD3167	Approved
0.5848	Remote Similarity	NPD4466	Phase 1
0.5845	Remote Similarity	NPD6677	Suspended
0.5826	Remote Similarity	NPD1298	Discontinued
0.5817	Remote Similarity	NPD7317	Phase 3
0.5806	Remote Similarity	NPD2325	Approved
0.5805	Remote Similarity	NPD5586	Clinical (unspecified phase)
0.5795	Remote Similarity	NPD3162	Approved
0.5795	Remote Similarity	NPD3163	Approved
0.5787	Remote Similarity	NPD6620	Discovery
0.5785	Remote Similarity	NPD6377	Clinical (unspecified phase)
0.5784	Remote Similarity	NPD3985	Discontinued
0.5779	Remote Similarity	NPD2161	Phase 2
0.5773	Remote Similarity	NPD5163	Phase 2
0.5771	Remote Similarity	NPD4162	Approved
0.5767	Remote Similarity	NPD4575	Clinical (unspecified phase)
0.5767	Remote Similarity	NPD3451	Clinical (unspecified phase)
0.5762	Remote Similarity	NPD2296	Approved
0.5756	Remote Similarity	NPD1975	Clinical (unspecified phase)
0.5752	Remote Similarity	NPD4413	Clinical (unspecified phase)
0.5752	Remote Similarity	NPD7256	Discontinued
0.575	Remote Similarity	NPD3656	Approved
0.5749	Remote Similarity	NPD3769	Discontinued
0.5742	Remote Similarity	NPD5355	Approved
0.5742	Remote Similarity	NPD5356	Approved
0.5741	Remote Similarity	NPD5605	Phase 2
0.5729	Remote Similarity	NPD1794	Approved
0.5728	Remote Similarity	NPD2042	Clinical (unspecified phase)
0.5728	Remote Similarity	NPD2041	Clinical (unspecified phase)
0.5727	Remote Similarity	NPD7880	Clinical (unspecified phase)
0.5721	Remote Similarity	NPD2388	Discontinued
0.5721	Remote Similarity	NPD7596	Clinical (unspecified phase)
0.5721	Remote Similarity	NPD7565	Approved
0.5714	Remote Similarity	NPD1726	Clinical (unspecified phase)
0.5714	Remote Similarity	NPD5910	Clinical (unspecified phase)
0.5708	Remote Similarity	NPD1309	Phase 2
0.5708	Remote Similarity	NPD1307	Phase 2
0.5707	Remote Similarity	NPD6419	Discontinued
0.5707	Remote Similarity	NPD3054	Approved
0.5707	Remote Similarity	NPD3052	Approved
0.57	Remote Similarity	NPD3687	Approved
0.57	Remote Similarity	NPD5712	Approved
0.57	Remote Similarity	NPD3686	Approved
0.57	Remote Similarity	NPD4124	Clinical (unspecified phase)
0.5694	Remote Similarity	NPD7118	Clinical (unspecified phase)
0.5693	Remote Similarity	NPD2460	Phase 3
0.5693	Remote Similarity	NPD2458	Approved
0.5693	Remote Similarity	NPD2459	Approved
0.5688	Remote Similarity	NPD5095	Phase 3
0.5688	Remote Similarity	NPD5096	Phase 3
0.5688	Remote Similarity	NPD3933	Discontinued
0.5684	Remote Similarity	NPD7584	Approved
0.5682	Remote Similarity	NPD7038	Approved
0.5682	Remote Similarity	NPD7039	Approved
0.5681	Remote Similarity	NPD6862	Phase 2
0.568	Remote Similarity	NPD7527	Clinical (unspecified phase)
0.568	Remote Similarity	NPD52	Approved
0.568	Remote Similarity	NPD7526	Approved
0.568	Remote Similarity	NPD4186	Clinical (unspecified phase)
0.567	Remote Similarity	NPD2250	Discontinued
0.5664	Remote Similarity	NPD3269	Clinical (unspecified phase)
0.5663	Remote Similarity	NPD3056	Clinical (unspecified phase)
0.5662	Remote Similarity	NPD5557	Phase 1
0.5654	Remote Similarity	NPD2904	Discontinued
0.5652	Remote Similarity	NPD7810	Phase 3
0.5652	Remote Similarity	NPD7811	Phase 3
0.5644	Remote Similarity	NPD7153	Discontinued
0.5635	Remote Similarity	NPD5745	Approved
0.5635	Remote Similarity	NPD2245	Discovery
0.5631	Remote Similarity	NPD2874	Phase 2
0.5628	Remote Similarity	NPD6519	Phase 2
0.5625	Remote Similarity	NPD6793	Clinical (unspecified phase)
0.5625	Remote Similarity	NPD8398	Clinical (unspecified phase)
0.5616	Remote Similarity	NPD1416	Approved
0.561	Remote Similarity	NPD5295	Discontinued
0.5606	Remote Similarity	NPD3597	Clinical (unspecified phase)
0.5605	Remote Similarity	NPD6853	Approved
0.5605	Remote Similarity	NPD6851	Approved
0.5604	Remote Similarity	NPD2186	Approved
0.5604	Remote Similarity	NPD6390	Discontinued
0.5603	Remote Similarity	NPD7476	Discontinued
0.56	Remote Similarity	NPD7693	Approved
0.56	Remote Similarity	NPD3490	Discontinued

Bioactivity similarity: Similar Natural Products in NPASS

Bioactivity similarity was calculated based on bioactivity descriptors of compounds. The bioactivity descriptors were calculated by a recently developed AI algorithm Chemical Checker (CC) [Nature Biotechnology, 38:1087–1096, 2020; Nature Communications, 12:3932, 2021], which evaluated bioactivity similarities at five levels:
☉ A: chemistry similarity;
☉ B: biological targets similarity;
☉ C: networks similarity;
☉ D: cell-based bioactivity similarity;
☉ E: similarity based on clinical data.

Those 5 categories of CC bioactivity descriptors were calculated and then subjected to manifold projection using UMAP algorithm, to project all NPs on a 2-Dimensional space. The current NP was highlighted with a small circle in the 2-D map. Below figures: left-to-right, A-to-E.

A: chemistry similarity

B: biological targets similarity

C: networks similarity

D: cell-based bioactivity similarity

E: similarity based on clinical data