NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	3149.38
Volume:	3004.075
LogP:	-1.311
LogD:	3.185
LogS:	0.179
# Rotatable Bonds:	37
TPSA:	1282.27
# H-Bond Aceptor:	76
# H-Bond Donor:	46
# Rings:	10
# Heavy Atoms:	82

MedChem Properties

QED Drug-Likeness Score:	0.008
Synthetic Accessibility Score:	9.935
Fsp3:	0.642
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
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:	2.768
MDCK Permeability:	0.019853644
Pgp-inhibitor:	0
Pgp-substrate:	1
Human Intestinal Absorption (HIA):	1
20% Bioavailability (F20%):	1
30% Bioavailability (F30%):	0.999

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	1
Plasma Protein Binding (PPB):	26.85%
Volume Distribution (VD):	-1.823
Pgp-substrate:	67.90%

ADMET: Metabolism

CYP1A2-inhibitor:	0
CYP1A2-substrate:	0
CYP2C19-inhibitor:	0
CYP2C19-substrate:	0.001
CYP2C9-inhibitor:	0
CYP2C9-substrate:	0
CYP2D6-inhibitor:	0
CYP2D6-substrate:	0
CYP3A4-inhibitor:	0
CYP3A4-substrate:	0

ADMET: Excretion

Clearance (CL):	-4.338
Half-life (T1/2):	0.524

ADMET: Toxicity

hERG Blockers:	0
Human Hepatotoxicity (H-HT):	1
Drug-inuced Liver Injury (DILI):	0.98
AMES Toxicity:	0
Rat Oral Acute Toxicity:	0
Maximum Recommended Daily Dose:	0
Skin Sensitization:	0.864
Carcinogencity:	0.013
Eye Corrosion:	0.003
Eye Irritation:	0.017
Respiratory Toxicity:	0.947

Download Data

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

Natural Product: NPC477630

Natural Product ID:	NPC477630
*Common Name:**	cyclo[Ala-Ala-Leu-Gly-Cys(1)-Ser-Cys(2)-Lys-Asn-Lys-Val-Cys(3)-Tyr-Arg-Asn-Gly-Ile-Pro-Cys(1)-Gly-Glu-Ser-Cys(2)-Val-Trp-Ile-Pro-Cys(3)-Ile-Ser]
IUPAC Name:	3-[(1R,4S,7S,13R,16S,22S,28S,31S,34S,37R,40S,43S,46S,49S,52R,55S,58R,64S,67S,70S,73S,76S,79R,82S,88S,91S,94S)-43,49-bis(4-aminobutyl)-28,46-bis(2-amino-2-oxoethyl)-22,76,88-tris[(2S)-butan-2-yl]-31-(3-carbamimidamidopropyl)-4,55,73-tris(hydroxymethyl)-34-[(4-hydroxyphenyl)methyl]-91-(1H-indol-3-ylmethyl)-67,70-dimethyl-64-(2-methylpropyl)-3,6,9,12,15,21,24,27,30,33,36,39,42,45,48,51,54,57,60,63,66,69,72,75,78,81,87,90,93,96-triacontaoxo-40,94-di(propan-2-yl)-2a,3a,6a,7a,98,99-hexathia-2,5,8,11,14,20,23,26,29,32,35,38,41,44,47,50,53,56,59,62,65,68,71,74,77,80,86,89,92,95-triacontazahexacyclo[50.44.4.413,58.437,79.016,20.082,86]octahectan-7-yl]propanoic acid
Synonyms:	Circulin A
Standard InCHIKey:	OEDKDVKQFDPTHK-UBIDWWFKSA-N
Standard InCHI:	InChI=1S/C134H208N38O38S6/c1-15-66(10)104-131(208)160-85(54-173)119(196)147-69(13)107(184)146-70(14)108(185)153-80(45-63(4)5)109(186)143-52-99(180)149-89-58-212-211-57-88-111(188)145-51-98(179)148-79(38-39-101(182)183)114(191)158-86(55-174)120(197)162-92-61-215-213-59-90(161-121(198)87(56-175)159-122(89)199)123(200)152-76(29-20-22-40-135)112(189)156-84(49-97(138)178)117(194)150-77(30-21-23-41-136)115(192)167-103(65(8)9)130(207)165-91(60-214-216-62-93(126(203)169-104)164-128(205)95-33-26-44-172(95)133(210)106(68(12)17-3)170-118(195)82(157-129(206)102(64(6)7)168-125(92)202)47-72-50-142-75-28-19-18-27-74(72)75)124(201)154-81(46-71-34-36-73(176)37-35-71)116(193)151-78(31-24-42-141-134(139)140)113(190)155-83(48-96(137)177)110(187)144-53-100(181)166-105(67(11)16-2)132(209)171-43-25-32-94(171)127(204)163-88/h18-19,27-28,34-37,50,63-70,76-95,102-106,142,173-176H,15-17,20-26,29-33,38-49,51-62,135-136H2,1-14H3,(H2,137,177)(H2,138,178)(H,143,186)(H,144,187)(H,145,188)(H,146,184)(H,147,196)(H,148,179)(H,149,180)(H,150,194)(H,151,193)(H,152,200)(H,153,185)(H,154,201)(H,155,190)(H,156,189)(H,157,206)(H,158,191)(H,159,199)(H,160,208)(H,161,198)(H,162,197)(H,163,204)(H,164,205)(H,165,207)(H,166,181)(H,167,192)(H,168,202)(H,169,203)(H,170,195)(H,182,183)(H4,139,140,141)/t66-,67-,68-,69-,70-,76-,77-,78-,79-,80-,81-,82-,83-,84-,85-,86-,87-,88-,89-,90-,91-,92-,93-,94-,95-,102-,103-,104-,105-,106-/m0/s1
SMILES:	CC[C@H](C)[C@H]1C(=O)N[C@H](C(=O)N[C@H](C(=O)N[C@H](C(=O)N[C@H](C(=O)NCC(=O)N[C@H]2CSSC[C@H]3C(=O)NCC(=O)N[C@H](C(=O)N[C@H](C(=O)N[C@H]4CSSC[C@@H](C(=O)N[C@H](C(=O)N[C@H](C(=O)N[C@H](C(=O)N[C@H](C(=O)N[C@@H](CSSC[C@@H](C(=O)N1)NC(=O)[C@@H]5CCCN5C(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@@H](NC4=O)C(C)C)CC6=CNC7=CC=CC=C76)[C@@H](C)CC)C(=O)N[C@H](C(=O)N[C@H](C(=O)N[C@H](C(=O)NCC(=O)N[C@H](C(=O)N8CCC[C@H]8C(=O)N3)[C@@H](C)CC)CC(=O)N)CCCNC(=N)N)CC9=CC=C(C=C9)O)C(C)C)CCCCN)CC(=O)N)CCCCN)NC(=O)[C@@H](NC2=O)CO)CO)CCC(=O)O)CC(C)C)C)C)CO
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	n.a.
PubChem CID:	44592641
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0003297] Organic Polymers [CHEMONTID:0003298] Polypeptides

*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
NPO33585	Palicourea condensata	Species	Rubiaceae	Eukaryota	Bark	Pastaza, Ecuador	1988-MAR	PMID[11430013]

☑ 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
EC50	3
IC50	1
MIC	4

Activity Type	# Activity
Organism	8

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT24	Organism	Human immunodeficiency virus 1	Human immunodeficiency virus 1	EC50	=	50	nM	PMID[11430013]
NPT24	Organism	Human immunodeficiency virus 1	Human immunodeficiency virus 1	EC50	=	40	nM	PMID[11678673]
NPT3153	Organism	Kluyveromyces marxianus	Kluyveromyces marxianus	MIC	=	18600	nM	PMID[20718473]
NPT186	Organism	Candida tropicalis	Candida tropicalis	MIC	=	19400	nM	PMID[20718473]
NPT766	Organism	Proteus vulgaris	Proteus vulgaris	MIC	=	54600	nM	PMID[20718473]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	=	190	nM	PMID[20718473]
NPT24	Organism	Human immunodeficiency virus 1	Human immunodeficiency virus 1	EC50	=	40	nM	PMID[20718473]
NPT24	Organism	Human immunodeficiency virus 1	Human immunodeficiency virus 1	IC50	=	500	nM	PMID[20718473]

☑ 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 NPC477630 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	422
0.1-0.2	2531
0.2-0.3	14112
0.3-0.4	16451
0.4-0.5	4388
0.5-0.6	3064
0.6-0.7	1441
0.7-0.8	227
0.8-0.85	34
0.85-0.9	16
0.9-0.95	3
0.95-1	8

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC477635
0.9163	High Similarity	NPC477634
0.8566	High Similarity	NPC477633
0.8528	High Similarity	NPC28945
0.8487	Intermediate Similarity	NPC153400
0.8363	Intermediate Similarity	NPC473317
0.8319	Intermediate Similarity	NPC220852
0.8253	Intermediate Similarity	NPC125597
0.8223	Intermediate Similarity	NPC314882
0.8213	Intermediate Similarity	NPC285343
0.819	Intermediate Similarity	NPC326363
0.8145	Intermediate Similarity	NPC314056
0.8128	Intermediate Similarity	NPC325976
0.8125	Intermediate Similarity	NPC320968
0.8063	Intermediate Similarity	NPC478011
0.806	Intermediate Similarity	NPC319232
0.806	Intermediate Similarity	NPC24370
0.8048	Intermediate Similarity	NPC478013
0.8031	Intermediate Similarity	NPC314176
0.7968	Intermediate Similarity	NPC315467
0.7944	Intermediate Similarity	NPC478006
0.7922	Intermediate Similarity	NPC478012
0.7897	Intermediate Similarity	NPC64216
0.7866	Intermediate Similarity	NPC478009
0.7857	Intermediate Similarity	NPC323752
0.7782	Intermediate Similarity	NPC321939
0.7773	Intermediate Similarity	NPC75634
0.7741	Intermediate Similarity	NPC89987
0.7739	Intermediate Similarity	NPC54744
0.7725	Intermediate Similarity	NPC478010
0.7718	Intermediate Similarity	NPC478028
0.7699	Intermediate Similarity	NPC473376
0.7682	Intermediate Similarity	NPC477631
0.7671	Intermediate Similarity	NPC477636
0.7654	Intermediate Similarity	NPC478029
0.7634	Intermediate Similarity	NPC100321
0.7611	Intermediate Similarity	NPC155143
0.7578	Intermediate Similarity	NPC477639
0.7566	Intermediate Similarity	NPC475506
0.7531	Intermediate Similarity	NPC214142
0.7521	Intermediate Similarity	NPC328924
0.7521	Intermediate Similarity	NPC321592
0.7521	Intermediate Similarity	NPC54803
0.7511	Intermediate Similarity	NPC473640
0.751	Intermediate Similarity	NPC223409
0.751	Intermediate Similarity	NPC263117
0.751	Intermediate Similarity	NPC95240
0.751	Intermediate Similarity	NPC322135
0.751	Intermediate Similarity	NPC242872
0.751	Intermediate Similarity	NPC125181
0.75	Intermediate Similarity	NPC323244
0.75	Intermediate Similarity	NPC261251
0.7489	Intermediate Similarity	NPC107077
0.7489	Intermediate Similarity	NPC162860
0.7489	Intermediate Similarity	NPC223791
0.7478	Intermediate Similarity	NPC293917
0.7478	Intermediate Similarity	NPC54420
0.7469	Intermediate Similarity	NPC100547
0.7458	Intermediate Similarity	NPC281049
0.7455	Intermediate Similarity	NPC477632
0.7455	Intermediate Similarity	NPC477638
0.7427	Intermediate Similarity	NPC304307
0.7427	Intermediate Similarity	NPC34580
0.7427	Intermediate Similarity	NPC124920
0.7427	Intermediate Similarity	NPC118559
0.7414	Intermediate Similarity	NPC478158
0.7407	Intermediate Similarity	NPC14288
0.7404	Intermediate Similarity	NPC478157
0.7403	Intermediate Similarity	NPC323927
0.7393	Intermediate Similarity	NPC75726
0.7393	Intermediate Similarity	NPC110602
0.7393	Intermediate Similarity	NPC31385
0.7357	Intermediate Similarity	NPC171317
0.7349	Intermediate Similarity	NPC295452
0.7349	Intermediate Similarity	NPC171393
0.7347	Intermediate Similarity	NPC284888
0.7311	Intermediate Similarity	NPC264285
0.7309	Intermediate Similarity	NPC213629
0.7295	Intermediate Similarity	NPC69843
0.7276	Intermediate Similarity	NPC323198
0.7261	Intermediate Similarity	NPC16352
0.7247	Intermediate Similarity	NPC33064
0.7247	Intermediate Similarity	NPC245055
0.7237	Intermediate Similarity	NPC156704
0.7236	Intermediate Similarity	NPC165743
0.7229	Intermediate Similarity	NPC82472
0.7229	Intermediate Similarity	NPC476874
0.7217	Intermediate Similarity	NPC315491
0.7217	Intermediate Similarity	NPC45459
0.7213	Intermediate Similarity	NPC244536
0.7208	Intermediate Similarity	NPC313804
0.7208	Intermediate Similarity	NPC315804
0.7206	Intermediate Similarity	NPC63279
0.7195	Intermediate Similarity	NPC477177
0.7195	Intermediate Similarity	NPC475969
0.7195	Intermediate Similarity	NPC475859
0.7195	Intermediate Similarity	NPC474877
0.7177	Intermediate Similarity	NPC297642
0.7154	Intermediate Similarity	NPC470730
0.7154	Intermediate Similarity	NPC477175
0.7154	Intermediate Similarity	NPC470729
0.7154	Intermediate Similarity	NPC477176
0.7125	Intermediate Similarity	NPC79386
0.7117	Intermediate Similarity	NPC477637
0.7106	Intermediate Similarity	NPC316403
0.7095	Intermediate Similarity	NPC303658
0.708	Intermediate Similarity	NPC272549
0.7071	Intermediate Similarity	NPC229348
0.7052	Intermediate Similarity	NPC184225
0.7047	Intermediate Similarity	NPC477109
0.7047	Intermediate Similarity	NPC477107
0.7047	Intermediate Similarity	NPC477108
0.7039	Intermediate Similarity	NPC300183
0.7034	Intermediate Similarity	NPC88008
0.7024	Intermediate Similarity	NPC41679
0.7012	Intermediate Similarity	NPC74969
0.7009	Intermediate Similarity	NPC193761
0.7008	Intermediate Similarity	NPC201831
0.7008	Intermediate Similarity	NPC17487
0.7004	Intermediate Similarity	NPC476491
0.7004	Intermediate Similarity	NPC32771
0.6996	Remote Similarity	NPC213308
0.6991	Remote Similarity	NPC94752
0.6987	Remote Similarity	NPC99666
0.6984	Remote Similarity	NPC15801
0.6979	Remote Similarity	NPC476098
0.697	Remote Similarity	NPC242209
0.6966	Remote Similarity	NPC117980
0.696	Remote Similarity	NPC46580
0.6957	Remote Similarity	NPC470784
0.695	Remote Similarity	NPC181081
0.6949	Remote Similarity	NPC470500
0.6947	Remote Similarity	NPC475746
0.6944	Remote Similarity	NPC477549
0.694	Remote Similarity	NPC77555
0.6923	Remote Similarity	NPC470497
0.692	Remote Similarity	NPC74619
0.6916	Remote Similarity	NPC171171
0.6911	Remote Similarity	NPC478141
0.691	Remote Similarity	NPC306376
0.6908	Remote Similarity	NPC194740
0.6897	Remote Similarity	NPC329295
0.6886	Remote Similarity	NPC17059
0.6885	Remote Similarity	NPC477714
0.6875	Remote Similarity	NPC5145
0.6875	Remote Similarity	NPC473312
0.6872	Remote Similarity	NPC314002
0.687	Remote Similarity	NPC60621
0.6867	Remote Similarity	NPC6215
0.6862	Remote Similarity	NPC258062
0.6862	Remote Similarity	NPC127677
0.686	Remote Similarity	NPC282247
0.6857	Remote Similarity	NPC74360
0.6853	Remote Similarity	NPC294693
0.685	Remote Similarity	NPC184680
0.6844	Remote Similarity	NPC238945
0.684	Remote Similarity	NPC33949
0.6836	Remote Similarity	NPC81175
0.6835	Remote Similarity	NPC98715
0.6833	Remote Similarity	NPC271862
0.6829	Remote Similarity	NPC276657
0.6828	Remote Similarity	NPC204717
0.6824	Remote Similarity	NPC470785
0.6822	Remote Similarity	NPC78609
0.682	Remote Similarity	NPC46225
0.682	Remote Similarity	NPC225821
0.6818	Remote Similarity	NPC151976
0.6818	Remote Similarity	NPC87856
0.6818	Remote Similarity	NPC63109
0.6816	Remote Similarity	NPC475736
0.6816	Remote Similarity	NPC469594
0.6809	Remote Similarity	NPC39092
0.6803	Remote Similarity	NPC470732
0.6803	Remote Similarity	NPC132211
0.6803	Remote Similarity	NPC203614
0.6803	Remote Similarity	NPC470731
0.6803	Remote Similarity	NPC204491
0.6802	Remote Similarity	NPC2395
0.6802	Remote Similarity	NPC474896
0.68	Remote Similarity	NPC186351
0.6797	Remote Similarity	NPC117244
0.6797	Remote Similarity	NPC477861
0.6797	Remote Similarity	NPC473763
0.679	Remote Similarity	NPC471080
0.679	Remote Similarity	NPC469592
0.679	Remote Similarity	NPC267965
0.6787	Remote Similarity	NPC19170
0.6787	Remote Similarity	NPC235885
0.6784	Remote Similarity	NPC220765
0.6783	Remote Similarity	NPC321708
0.678	Remote Similarity	NPC249040
0.6776	Remote Similarity	NPC304926
0.6776	Remote Similarity	NPC476041
0.6776	Remote Similarity	NPC477715
0.6776	Remote Similarity	NPC472285
0.6776	Remote Similarity	NPC305984
0.6774	Remote Similarity	NPC31097
0.6774	Remote Similarity	NPC155444
0.6771	Remote Similarity	NPC314603
0.6766	Remote Similarity	NPC131887

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 NPC477630 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	192
0.1-0.2	581
0.2-0.3	880
0.3-0.4	1700
0.4-0.5	2807
0.5-0.6	2286
0.6-0.7	671
0.7-0.8	30
0.8-0.85	3
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.7939	Intermediate Similarity	NPD7970	Approved
0.7939	Intermediate Similarity	NPD7971	Clinical (unspecified phase)
0.7913	Intermediate Similarity	NPD8405	Clinical (unspecified phase)
0.7632	Intermediate Similarity	NPD8493	Clinical (unspecified phase)
0.7621	Intermediate Similarity	NPD8272	Phase 2
0.7573	Intermediate Similarity	NPD8292	Phase 2
0.7478	Intermediate Similarity	NPD7621	Clinical (unspecified phase)
0.7457	Intermediate Similarity	NPD7809	Clinical (unspecified phase)
0.7425	Intermediate Similarity	NPD7470	Discontinued
0.7386	Intermediate Similarity	NPD7711	Discontinued
0.7342	Intermediate Similarity	NPD8406	Clinical (unspecified phase)
0.7314	Intermediate Similarity	NPD7603	Discontinued
0.7305	Intermediate Similarity	NPD8255	Phase 2
0.7237	Intermediate Similarity	NPD7948	Phase 1
0.7217	Intermediate Similarity	NPD484	Approved
0.7213	Intermediate Similarity	NPD4086	Phase 1
0.7203	Intermediate Similarity	NPD8013	Clinical (unspecified phase)
0.7176	Intermediate Similarity	NPD8284	Discontinued
0.7124	Intermediate Similarity	NPD8072	Approved
0.7116	Intermediate Similarity	NPD7655	Discontinued
0.7009	Intermediate Similarity	NPD8073	Approved
0.6983	Remote Similarity	NPD7823	Clinical (unspecified phase)
0.6949	Remote Similarity	NPD8169	Discontinued
0.693	Remote Similarity	NPD8110	Clinical (unspecified phase)
0.6926	Remote Similarity	NPD8421	Discontinued
0.6903	Remote Similarity	NPD2091	Phase 2
0.6903	Remote Similarity	NPD2096	Phase 2
0.6894	Remote Similarity	NPD7903	Clinical (unspecified phase)
0.686	Remote Similarity	NPD8094	Discontinued
0.6858	Remote Similarity	NPD2094	Phase 2
0.6858	Remote Similarity	NPD2095	Phase 2
0.6858	Remote Similarity	NPD2092	Phase 2
0.6852	Remote Similarity	NPD7689	Approved
0.6842	Remote Similarity	NPD6824	Clinical (unspecified phase)
0.684	Remote Similarity	NPD6665	Discontinued
0.6831	Remote Similarity	NPD8112	Clinical (unspecified phase)
0.682	Remote Similarity	NPD6838	Clinical (unspecified phase)
0.6818	Remote Similarity	NPD8093	Discontinued
0.6818	Remote Similarity	NPD7594	Clinical (unspecified phase)
0.681	Remote Similarity	NPD5575	Clinical (unspecified phase)
0.6803	Remote Similarity	NPD5612	Discontinued
0.68	Remote Similarity	NPD7730	Approved
0.68	Remote Similarity	NPD7731	Approved
0.68	Remote Similarity	NPD8430	Approved
0.6784	Remote Similarity	NPD8524	Approved
0.6784	Remote Similarity	NPD5728	Clinical (unspecified phase)
0.6781	Remote Similarity	NPD7944	Discontinued
0.6778	Remote Similarity	NPD7958	Clinical (unspecified phase)
0.6778	Remote Similarity	NPD7957	Phase 1
0.6774	Remote Similarity	NPD8356	Approved
0.675	Remote Similarity	NPD8322	Phase 2
0.6746	Remote Similarity	NPD7824	Approved
0.6738	Remote Similarity	NPD8525	Approved
0.6726	Remote Similarity	NPD8349	Phase 1
0.6722	Remote Similarity	NPD7947	Clinical (unspecified phase)
0.672	Remote Similarity	NPD7271	Approved
0.6708	Remote Similarity	NPD7001	Phase 3
0.6692	Remote Similarity	NPD7967	Discontinued
0.6681	Remote Similarity	NPD7818	Clinical (unspecified phase)
0.668	Remote Similarity	NPD3917	Approved
0.668	Remote Similarity	NPD3916	Clinical (unspecified phase)
0.668	Remote Similarity	NPD8458	Clinical (unspecified phase)
0.668	Remote Similarity	NPD3918	Approved
0.6667	Remote Similarity	NPD7825	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD7950	Approved
0.6667	Remote Similarity	NPD7953	Approved
0.6667	Remote Similarity	NPD5426	Phase 3
0.6667	Remote Similarity	NPD3814	Phase 1
0.6667	Remote Similarity	NPD7952	Approved
0.6667	Remote Similarity	NPD7789	Approved
0.6667	Remote Similarity	NPD7791	Approved
0.6667	Remote Similarity	NPD7790	Approved
0.6667	Remote Similarity	NPD7951	Approved
0.6667	Remote Similarity	NPD7998	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD5040	Clinical (unspecified phase)
0.6653	Remote Similarity	NPD2509	Approved
0.6653	Remote Similarity	NPD2187	Approved
0.6653	Remote Similarity	NPD2189	Approved
0.6653	Remote Similarity	NPD2510	Approved
0.6653	Remote Similarity	NPD8488	Clinical (unspecified phase)
0.664	Remote Similarity	NPD7780	Approved
0.664	Remote Similarity	NPD7781	Approved
0.6639	Remote Similarity	NPD4862	Clinical (unspecified phase)
0.6639	Remote Similarity	NPD3915	Approved
0.6623	Remote Similarity	NPD6595	Phase 3
0.6617	Remote Similarity	NPD8247	Approved
0.6617	Remote Similarity	NPD8246	Approved
0.6615	Remote Similarity	NPD3006	Discontinued
0.6602	Remote Similarity	NPD7558	Phase 2
0.6601	Remote Similarity	NPD6164	Phase 2
0.6601	Remote Similarity	NPD6165	Phase 2
0.6596	Remote Similarity	NPD1038	Approved
0.6596	Remote Similarity	NPD802	Phase 2
0.6593	Remote Similarity	NPD482	Approved
0.6586	Remote Similarity	NPD537	Phase 2
0.6586	Remote Similarity	NPD534	Phase 2
0.6583	Remote Similarity	NPD7181	Phase 3
0.658	Remote Similarity	NPD6344	Clinical (unspecified phase)
0.6579	Remote Similarity	NPD8370	Discontinued
0.6577	Remote Similarity	NPD7576	Discontinued
0.6575	Remote Similarity	NPD5559	Phase 2
0.6573	Remote Similarity	NPD7980	Clinical (unspecified phase)
0.657	Remote Similarity	NPD6732	Clinical (unspecified phase)
0.6564	Remote Similarity	NPD749	Clinical (unspecified phase)
0.6554	Remote Similarity	NPD8442	Discontinued
0.6553	Remote Similarity	NPD4558	Phase 2
0.6552	Remote Similarity	NPD3914	Clinical (unspecified phase)
0.6545	Remote Similarity	NPD8097	Phase 3
0.6545	Remote Similarity	NPD8096	Phase 3
0.6543	Remote Similarity	NPD8410	Clinical (unspecified phase)
0.654	Remote Similarity	NPD8310	Clinical (unspecified phase)
0.654	Remote Similarity	NPD8359	Phase 2
0.6533	Remote Similarity	NPD4184	Clinical (unspecified phase)
0.6532	Remote Similarity	NPD7112	Discontinued
0.6531	Remote Similarity	NPD7465	Suspended
0.6529	Remote Similarity	NPD8098	Approved
0.6529	Remote Similarity	NPD7712	Clinical (unspecified phase)
0.6527	Remote Similarity	NPD7000	Clinical (unspecified phase)
0.6527	Remote Similarity	NPD6999	Discontinued
0.6524	Remote Similarity	NPD6141	Clinical (unspecified phase)
0.6516	Remote Similarity	NPD4960	Approved
0.6516	Remote Similarity	NPD7666	Phase 3
0.6516	Remote Similarity	NPD4959	Approved
0.6516	Remote Similarity	NPD7665	Phase 2
0.6506	Remote Similarity	NPD8271	Discontinued
0.6506	Remote Similarity	NPD8257	Approved
0.6506	Remote Similarity	NPD8258	Clinical (unspecified phase)
0.6506	Remote Similarity	NPD8256	Approved
0.6502	Remote Similarity	NPD5483	Clinical (unspecified phase)
0.6498	Remote Similarity	NPD4885	Approved
0.6496	Remote Similarity	NPD8289	Discontinued
0.6491	Remote Similarity	NPD4887	Discontinued
0.6488	Remote Similarity	NPD2121	Clinical (unspecified phase)
0.6485	Remote Similarity	NPD53	Approved
0.6485	Remote Similarity	NPD7777	Approved
0.6485	Remote Similarity	NPD7778	Approved
0.6484	Remote Similarity	NPD7589	Clinical (unspecified phase)
0.6476	Remote Similarity	NPD750	Phase 2
0.6475	Remote Similarity	NPD8017	Clinical (unspecified phase)
0.6475	Remote Similarity	NPD8016	Phase 3
0.6475	Remote Similarity	NPD1392	Approved
0.6475	Remote Similarity	NPD2921	Clinical (unspecified phase)
0.6473	Remote Similarity	NPD8303	Discontinued
0.6473	Remote Similarity	NPD8364	Approved
0.6473	Remote Similarity	NPD4511	Phase 1
0.6473	Remote Similarity	NPD8363	Approved
0.6471	Remote Similarity	NPD6449	Clinical (unspecified phase)
0.6468	Remote Similarity	NPD7617	Discontinued
0.6468	Remote Similarity	NPD7726	Phase 1
0.6466	Remote Similarity	NPD5482	Discontinued
0.6463	Remote Similarity	NPD8261	Discontinued
0.6462	Remote Similarity	NPD5018	Phase 3
0.6461	Remote Similarity	NPD5901	Discontinued
0.6459	Remote Similarity	NPD8106	Phase 2
0.6456	Remote Similarity	NPD1304	Clinical (unspecified phase)
0.6453	Remote Similarity	NPD6276	Discontinued
0.6449	Remote Similarity	NPD2916	Discontinued
0.644	Remote Similarity	NPD8000	Clinical (unspecified phase)
0.6434	Remote Similarity	NPD5015	Clinical (unspecified phase)
0.6431	Remote Similarity	NPD4438	Approved
0.6431	Remote Similarity	NPD8075	Discontinued
0.6429	Remote Similarity	NPD6242	Discontinued
0.6426	Remote Similarity	NPD7770	Phase 3
0.6426	Remote Similarity	NPD8365	Clinical (unspecified phase)
0.6426	Remote Similarity	NPD4897	Phase 2
0.6423	Remote Similarity	NPD2125	Clinical (unspecified phase)
0.6423	Remote Similarity	NPD7273	Clinical (unspecified phase)
0.6418	Remote Similarity	NPD6724	Clinical (unspecified phase)
0.6418	Remote Similarity	NPD8459	Approved
0.6418	Remote Similarity	NPD8460	Approved
0.6417	Remote Similarity	NPD7946	Pre-registration
0.6417	Remote Similarity	NPD6173	Approved
0.6414	Remote Similarity	NPD3354	Phase 2
0.6414	Remote Similarity	NPD7878	Phase 2
0.6411	Remote Similarity	NPD3330	Phase 1
0.641	Remote Similarity	NPD706	Phase 1
0.6406	Remote Similarity	NPD4845	Discontinued
0.6405	Remote Similarity	NPD7817	Phase 1
0.6403	Remote Similarity	NPD5147	Discontinued
0.64	Remote Similarity	NPD3394	Approved
0.64	Remote Similarity	NPD6803	Clinical (unspecified phase)
0.64	Remote Similarity	NPD3393	Approved
0.64	Remote Similarity	NPD3389	Approved
0.6397	Remote Similarity	NPD8321	Discontinued
0.6395	Remote Similarity	NPD8372	Clinical (unspecified phase)
0.6394	Remote Similarity	NPD8463	Approved
0.639	Remote Similarity	NPD2175	Phase 3
0.639	Remote Similarity	NPD8396	Approved
0.639	Remote Similarity	NPD8395	Approved
0.639	Remote Similarity	NPD2176	Approved
0.639	Remote Similarity	NPD2177	Approved
0.6387	Remote Similarity	NPD6456	Discontinued
0.6383	Remote Similarity	NPD3486	Clinical (unspecified phase)
0.6381	Remote Similarity	NPD7710	Clinical (unspecified phase)
0.6377	Remote Similarity	NPD7393	Clinical (unspecified phase)
0.6376	Remote Similarity	NPD5065	Approved
0.6375	Remote Similarity	NPD5003	Discontinued
0.6371	Remote Similarity	NPD5066	Phase 2
0.6371	Remote Similarity	NPD949	Phase 1
0.6371	Remote Similarity	NPD5067	Phase 2

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