NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	3281.5
Volume:	3151.284
LogP:	0.748
LogD:	3.548
LogS:	0.4
# Rotatable Bonds:	41
TPSA:	1319.3
# H-Bond Aceptor:	78
# H-Bond Donor:	47
# Rings:	8
# Heavy Atoms:	84

MedChem Properties

QED Drug-Likeness Score:	0.013
Synthetic Accessibility Score:	9.98
Fsp3:	0.667
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:	3.422
MDCK Permeability:	0.040993668
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):	28.35%
Volume Distribution (VD):	-2.088
Pgp-substrate:	68.78%

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):	-4.55
Half-life (T1/2):	0.57

ADMET: Toxicity

hERG Blockers:	0
Human Hepatotoxicity (H-HT):	1
Drug-inuced Liver Injury (DILI):	0.981
AMES Toxicity:	0
Rat Oral Acute Toxicity:	0
Maximum Recommended Daily Dose:	0
Skin Sensitization:	0.796
Carcinogencity:	0.006
Eye Corrosion:	0.003
Eye Irritation:	0.01
Respiratory Toxicity:	0.571

Download Data

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

Natural Product: NPC477631

Natural Product ID:	NPC477631
*Common Name:**	cyclo[Arg-Asn-Gly-Val-Ile-Pro-Cys(1)-Gly-Glu-Ser-Cys(2)-Val-Phe-Ile-Pro-Cys(3)-Ile-Ser-Thr-Leu-Leu-Gly-Cys(1)-Ser-Cys(2)-Lys-Asn-Lys-Val-Cys(3)-Tyr]
IUPAC Name:	3-[(1R,7S,10S,13R,16S,19S,22S,28S,31R,34S,37S,40S,43S,46S,52R,55S,58R,61S,64S,67S,70S,73R,76S,79S,82S,88S,91S,97S)-61,67-bis(4-aminobutyl)-64,82-bis(2-amino-2-oxoethyl)-19-benzyl-22,34,91-tris[(2S)-butan-2-yl]-79-(3-carbamimidamidopropyl)-40-[(1R)-1-hydroxyethyl]-10,37,55-tris(hydroxymethyl)-76-[(4-hydroxyphenyl)methyl]-43,46-bis(2-methylpropyl)-2,5,8,11,14,17,20,23,29,32,35,38,41,44,47,50,53,56,59,62,65,68,71,74,77,80,83,86,89,92,98-hentriacontaoxo-16,70,88-tri(propan-2-yl)-1a,2a,5a,6a,9a,10a-hexathia-3,6,9,12,15,18,21,24,30,33,36,39,42,45,48,51,54,57,60,63,66,69,72,75,78,81,84,87,90,93,99-hentriacontazahexacyclo[50.47.4.413,58.431,73.024,28.093,97]hendecahectan-7-yl]propanoic acid
Synonyms:
Standard InCHIKey:	QRZDNWCHQRFTOQ-OFSRULCSSA-N
Standard InCHI:	InChI=1S/C141H224N38O40S6/c1-18-72(14)109-137(216)165-91(60-182)126(205)177-112(75(17)183)138(217)161-84(50-68(6)7)120(199)157-83(49-67(4)5)113(192)149-56-103(188)153-93-62-221-220-61-92-115(194)151-55-102(187)152-82(42-43-105(190)191)118(197)163-89(58-180)124(203)167-96-65-224-222-63-94(166-125(204)90(59-181)164-127(93)206)128(207)156-79(33-24-26-44-142)116(195)160-88(54-101(145)186)122(201)154-80(34-25-27-45-143)119(198)172-108(71(12)13)135(214)170-95(64-223-225-66-97(131(210)174-109)169-133(212)99-37-30-47-178(99)139(218)110(73(15)19-2)175-123(202)86(51-76-31-22-21-23-32-76)162-134(213)107(70(10)11)173-130(96)209)129(208)158-85(52-77-38-40-78(184)41-39-77)121(200)155-81(35-28-46-148-141(146)147)117(196)159-87(53-100(144)185)114(193)150-57-104(189)171-106(69(8)9)136(215)176-111(74(16)20-3)140(219)179-48-29-36-98(179)132(211)168-92/h21-23,31-32,38-41,67-75,79-99,106-112,180-184H,18-20,24-30,33-37,42-66,142-143H2,1-17H3,(H2,144,185)(H2,145,186)(H,149,192)(H,150,193)(H,151,194)(H,152,187)(H,153,188)(H,154,201)(H,155,200)(H,156,207)(H,157,199)(H,158,208)(H,159,196)(H,160,195)(H,161,217)(H,162,213)(H,163,197)(H,164,206)(H,165,216)(H,166,204)(H,167,203)(H,168,211)(H,169,212)(H,170,214)(H,171,189)(H,172,198)(H,173,209)(H,174,210)(H,175,202)(H,176,215)(H,177,205)(H,190,191)(H4,146,147,148)/t72-,73-,74-,75+,79-,80-,81-,82-,83-,84-,85-,86-,87-,88-,89-,90-,91-,92-,93-,94-,95-,96-,97-,98-,99-,106-,107-,108-,109-,110-,111-,112-/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=CC=CC=C6)[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)N[C@H](C(=O)N7CCC[C@H]7C(=O)N3)[C@@H](C)CC)C(C)C)CC(=O)N)CCCNC(=N)N)CC8=CC=C(C=C8)O)C(C)C)CCCCN)CC(=O)N)CCCCN)NC(=O)[C@@H](NC2=O)CO)CO)CCC(=O)O)CC(C)C)CC(C)C)[C@@H](C)O)CO
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	n.a.
PubChem CID:	44592642
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	2
MIC	6

Activity Type	# Activity
Cell Line	1
Organism	10

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT7275	Cell Line	R1	Mus musculus	IC50	=	820000	nM	PMID[20718473]
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	=	29000	nM	PMID[20718473]
NPT19	Organism	Escherichia coli	Escherichia coli	MIC	=	410	nM	PMID[20718473]
NPT4997	Organism	Klebsiella oxytoca	Klebsiella oxytoca	MIC	=	8200	nM	PMID[20718473]
NPT18	Organism	Pseudomonas aeruginosa	Pseudomonas aeruginosa	MIC	=	25500	nM	PMID[20718473]
NPT766	Organism	Proteus vulgaris	Proteus vulgaris	MIC	=	6800	nM	PMID[20718473]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	=	13500	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 NPC477631 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	212
0.1-0.2	1218
0.2-0.3	6427
0.3-0.4	11791
0.4-0.5	18947
0.5-0.6	3314
0.6-0.7	485
0.7-0.8	235
0.8-0.85	39
0.85-0.9	9
0.9-0.95	6
0.95-1	14

Similarity Score	Similarity Level	Natural Product ID
0.9882	High Similarity	NPC477636
0.9713	High Similarity	NPC477639
0.9655	High Similarity	NPC477638
0.9655	High Similarity	NPC477632
0.9244	High Similarity	NPC477637
0.8743	High Similarity	NPC329295
0.8492	Intermediate Similarity	NPC473404
0.827	Intermediate Similarity	NPC60516
0.8256	Intermediate Similarity	NPC326349
0.8256	Intermediate Similarity	NPC323336
0.8216	Intermediate Similarity	NPC102959
0.8182	Intermediate Similarity	NPC61004
0.8172	Intermediate Similarity	NPC240130
0.8172	Intermediate Similarity	NPC61332
0.8101	Intermediate Similarity	NPC328494
0.8073	Intermediate Similarity	NPC477551
0.8045	Intermediate Similarity	NPC46009
0.8045	Intermediate Similarity	NPC475123
0.8045	Intermediate Similarity	NPC475204
0.8033	Intermediate Similarity	NPC153554
0.8011	Intermediate Similarity	NPC471165
0.7989	Intermediate Similarity	NPC280022
0.7969	Intermediate Similarity	NPC477552
0.7969	Intermediate Similarity	NPC477550
0.7968	Intermediate Similarity	NPC94862
0.7947	Intermediate Similarity	NPC302715
0.7944	Intermediate Similarity	NPC198254
0.7944	Intermediate Similarity	NPC274198
0.7919	Intermediate Similarity	NPC56685
0.7889	Intermediate Similarity	NPC129486
0.788	Intermediate Similarity	NPC97526
0.788	Intermediate Similarity	NPC119652
0.7857	Intermediate Similarity	NPC475532
0.7845	Intermediate Similarity	NPC276506
0.7816	Intermediate Similarity	NPC262166
0.7814	Intermediate Similarity	NPC17698
0.7814	Intermediate Similarity	NPC165285
0.7772	Intermediate Similarity	NPC196243
0.7742	Intermediate Similarity	NPC475564
0.7742	Intermediate Similarity	NPC475409
0.7742	Intermediate Similarity	NPC170302
0.7727	Intermediate Similarity	NPC244509
0.7709	Intermediate Similarity	NPC241794
0.77	Intermediate Similarity	NPC478005
0.7697	Intermediate Similarity	NPC244336
0.7682	Intermediate Similarity	NPC477635
0.7682	Intermediate Similarity	NPC477630
0.7676	Intermediate Similarity	NPC50016
0.7673	Intermediate Similarity	NPC469445
0.7663	Intermediate Similarity	NPC306804
0.7663	Intermediate Similarity	NPC137627
0.7654	Intermediate Similarity	NPC469243
0.765	Intermediate Similarity	NPC220060
0.7637	Intermediate Similarity	NPC107938
0.7637	Intermediate Similarity	NPC294516
0.7637	Intermediate Similarity	NPC328649
0.7637	Intermediate Similarity	NPC302597
0.7634	Intermediate Similarity	NPC473546
0.7627	Intermediate Similarity	NPC473580
0.7624	Intermediate Similarity	NPC63931
0.7614	Intermediate Similarity	NPC202198
0.7614	Intermediate Similarity	NPC469443
0.7612	Intermediate Similarity	NPC469444
0.7602	Intermediate Similarity	NPC77905
0.7568	Intermediate Similarity	NPC273755
0.7556	Intermediate Similarity	NPC475544
0.7554	Intermediate Similarity	NPC40234
0.7527	Intermediate Similarity	NPC473402
0.7527	Intermediate Similarity	NPC26108
0.7527	Intermediate Similarity	NPC223207
0.7514	Intermediate Similarity	NPC230611
0.7514	Intermediate Similarity	NPC5194
0.7514	Intermediate Similarity	NPC261934
0.75	Intermediate Similarity	NPC194671
0.75	Intermediate Similarity	NPC45037
0.75	Intermediate Similarity	NPC473491
0.75	Intermediate Similarity	NPC269750
0.75	Intermediate Similarity	NPC96275
0.7486	Intermediate Similarity	NPC290755
0.7486	Intermediate Similarity	NPC304074
0.7486	Intermediate Similarity	NPC471771
0.7433	Intermediate Similarity	NPC476227
0.7433	Intermediate Similarity	NPC136797
0.7433	Intermediate Similarity	NPC159767
0.7433	Intermediate Similarity	NPC155506
0.743	Intermediate Similarity	NPC476268
0.7423	Intermediate Similarity	NPC51047
0.7419	Intermediate Similarity	NPC89831
0.7381	Intermediate Similarity	NPC478007
0.738	Intermediate Similarity	NPC248670
0.7363	Intermediate Similarity	NPC114806
0.736	Intermediate Similarity	NPC300443
0.7351	Intermediate Similarity	NPC63040
0.735	Intermediate Similarity	NPC473450
0.7348	Intermediate Similarity	NPC324850
0.734	Intermediate Similarity	NPC279871
0.734	Intermediate Similarity	NPC473354
0.7337	Intermediate Similarity	NPC472923
0.733	Intermediate Similarity	NPC16188
0.733	Intermediate Similarity	NPC476321
0.733	Intermediate Similarity	NPC311658
0.7311	Intermediate Similarity	NPC478008
0.7308	Intermediate Similarity	NPC62104
0.7308	Intermediate Similarity	NPC1390
0.7308	Intermediate Similarity	NPC24617
0.7306	Intermediate Similarity	NPC299806
0.7297	Intermediate Similarity	NPC15068
0.7283	Intermediate Similarity	NPC48202
0.7282	Intermediate Similarity	NPC246591
0.7273	Intermediate Similarity	NPC80514
0.726	Intermediate Similarity	NPC25539
0.7249	Intermediate Similarity	NPC158277
0.7243	Intermediate Similarity	NPC210377
0.7243	Intermediate Similarity	NPC5719
0.7243	Intermediate Similarity	NPC217804
0.7243	Intermediate Similarity	NPC22883
0.7241	Intermediate Similarity	NPC476989
0.7222	Intermediate Similarity	NPC473341
0.722	Intermediate Similarity	NPC219350
0.722	Intermediate Similarity	NPC194699
0.7208	Intermediate Similarity	NPC470728
0.7202	Intermediate Similarity	NPC471526
0.7202	Intermediate Similarity	NPC470903
0.7202	Intermediate Similarity	NPC470112
0.7202	Intermediate Similarity	NPC167763
0.7184	Intermediate Similarity	NPC214988
0.7166	Intermediate Similarity	NPC209463
0.7166	Intermediate Similarity	NPC141957
0.7163	Intermediate Similarity	NPC469442
0.7163	Intermediate Similarity	NPC277306
0.7136	Intermediate Similarity	NPC328763
0.7128	Intermediate Similarity	NPC66490
0.7128	Intermediate Similarity	NPC473000
0.7113	Intermediate Similarity	NPC477634
0.7111	Intermediate Similarity	NPC7817
0.7111	Intermediate Similarity	NPC475168
0.7102	Intermediate Similarity	NPC91953
0.71	Intermediate Similarity	NPC184933
0.71	Intermediate Similarity	NPC59827
0.7088	Intermediate Similarity	NPC470902
0.7079	Intermediate Similarity	NPC81026
0.7077	Intermediate Similarity	NPC471048
0.7077	Intermediate Similarity	NPC471049
0.7077	Intermediate Similarity	NPC471050
0.7077	Intermediate Similarity	NPC294951
0.7072	Intermediate Similarity	NPC233702
0.7071	Intermediate Similarity	NPC473305
0.7071	Intermediate Similarity	NPC163961
0.7068	Intermediate Similarity	NPC477462
0.7056	Intermediate Similarity	NPC4910
0.7052	Intermediate Similarity	NPC141050
0.7047	Intermediate Similarity	NPC475421
0.7045	Intermediate Similarity	NPC197921
0.7035	Intermediate Similarity	NPC248822
0.7022	Intermediate Similarity	NPC266741
0.7022	Intermediate Similarity	NPC315266
0.7006	Intermediate Similarity	NPC469360
0.7006	Intermediate Similarity	NPC168861
0.6995	Remote Similarity	NPC477527
0.6995	Remote Similarity	NPC323662
0.6995	Remote Similarity	NPC39431
0.697	Remote Similarity	NPC329731
0.6966	Remote Similarity	NPC476978
0.6965	Remote Similarity	NPC65714
0.6954	Remote Similarity	NPC267237
0.695	Remote Similarity	NPC473407
0.695	Remote Similarity	NPC473378
0.6932	Remote Similarity	NPC242159
0.6932	Remote Similarity	NPC313694
0.6931	Remote Similarity	NPC254700
0.6923	Remote Similarity	NPC246303
0.6898	Remote Similarity	NPC469901
0.6897	Remote Similarity	NPC473371
0.6897	Remote Similarity	NPC287401
0.6889	Remote Similarity	NPC314358
0.6872	Remote Similarity	NPC326241
0.6868	Remote Similarity	NPC2501
0.6866	Remote Similarity	NPC477526
0.6863	Remote Similarity	NPC471592
0.6859	Remote Similarity	NPC186617
0.6848	Remote Similarity	NPC122590
0.6839	Remote Similarity	NPC326966
0.6833	Remote Similarity	NPC316008
0.6833	Remote Similarity	NPC313867
0.6823	Remote Similarity	NPC473693
0.6823	Remote Similarity	NPC471568
0.6816	Remote Similarity	NPC328924
0.6798	Remote Similarity	NPC314083
0.6794	Remote Similarity	NPC81845
0.6792	Remote Similarity	NPC295795
0.6791	Remote Similarity	NPC297145
0.6791	Remote Similarity	NPC197743
0.6787	Remote Similarity	NPC323244
0.6782	Remote Similarity	NPC130309
0.678	Remote Similarity	NPC64205
0.6778	Remote Similarity	NPC314388
0.6778	Remote Similarity	NPC315283
0.6772	Remote Similarity	NPC73655
0.6771	Remote Similarity	NPC315388
0.6769	Remote Similarity	NPC469900

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 NPC477631 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	129
0.1-0.2	400
0.2-0.3	728
0.3-0.4	2014
0.4-0.5	3931
0.5-0.6	1726
0.6-0.7	209
0.7-0.8	12
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8286	Intermediate Similarity	NPD8303	Discontinued
0.7841	Intermediate Similarity	NPD7118	Clinical (unspecified phase)
0.7614	Intermediate Similarity	NPD7523	Phase 3
0.7403	Intermediate Similarity	NPD7495	Discontinued
0.7403	Intermediate Similarity	NPD8019	Approved
0.7366	Intermediate Similarity	NPD4652	Approved
0.7299	Intermediate Similarity	NPD7978	Discontinued
0.72	Intermediate Similarity	NPD8076	Discontinued
0.7151	Intermediate Similarity	NPD2098	Approved
0.7088	Intermediate Similarity	NPD6670	Clinical (unspecified phase)
0.7072	Intermediate Similarity	NPD7303	Discontinued
0.7071	Intermediate Similarity	NPD7617	Discontinued
0.7043	Intermediate Similarity	NPD2097	Approved
0.6979	Remote Similarity	NPD5200	Clinical (unspecified phase)
0.6978	Remote Similarity	NPD6078	Clinical (unspecified phase)
0.6977	Remote Similarity	NPD3136	Phase 2
0.6932	Remote Similarity	NPD6901	Phase 3
0.6923	Remote Similarity	NPD5348	Clinical (unspecified phase)
0.6893	Remote Similarity	NPD6866	Clinical (unspecified phase)
0.6893	Remote Similarity	NPD6867	Clinical (unspecified phase)
0.6864	Remote Similarity	NPD8292	Phase 2
0.68	Remote Similarity	NPD6089	Clinical (unspecified phase)
0.6788	Remote Similarity	NPD5137	Approved
0.6778	Remote Similarity	NPD5341	Clinical (unspecified phase)
0.6776	Remote Similarity	NPD6682	Clinical (unspecified phase)
0.6771	Remote Similarity	NPD2890	Approved
0.6771	Remote Similarity	NPD2889	Approved
0.6771	Remote Similarity	NPD2888	Approved
0.6771	Remote Similarity	NPD2017	Approved
0.6712	Remote Similarity	NPD6796	Discontinued
0.6685	Remote Similarity	NPD7892	Clinical (unspecified phase)
0.6685	Remote Similarity	NPD4782	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD4791	Clinical (unspecified phase)
0.6651	Remote Similarity	NPD6254	Approved
0.6651	Remote Similarity	NPD6256	Approved
0.6651	Remote Similarity	NPD6255	Approved
0.6636	Remote Similarity	NPD3803	Clinical (unspecified phase)
0.663	Remote Similarity	NPD8290	Clinical (unspecified phase)
0.6612	Remote Similarity	NPD7066	Clinical (unspecified phase)
0.661	Remote Similarity	NPD5729	Clinical (unspecified phase)
0.6603	Remote Similarity	NPD6253	Approved
0.6598	Remote Similarity	NPD7485	Phase 3
0.6598	Remote Similarity	NPD7484	Phase 3
0.6592	Remote Similarity	NPD8172	Phase 2
0.6592	Remote Similarity	NPD8173	Phase 2
0.6554	Remote Similarity	NPD1330	Phase 2
0.6554	Remote Similarity	NPD1329	Clinical (unspecified phase)
0.6545	Remote Similarity	NPD4566	Approved
0.6545	Remote Similarity	NPD4567	Approved
0.6544	Remote Similarity	NPD6189	Approved
0.6544	Remote Similarity	NPD6188	Approved
0.6538	Remote Similarity	NPD6809	Clinical (unspecified phase)
0.6524	Remote Similarity	NPD7613	Discontinued
0.6498	Remote Similarity	NPD6187	Approved
0.6484	Remote Similarity	NPD7450	Phase 2
0.648	Remote Similarity	NPD5323	Approved
0.6461	Remote Similarity	NPD3632	Clinical (unspecified phase)
0.6457	Remote Similarity	NPD2585	Clinical (unspecified phase)
0.6453	Remote Similarity	NPD5946	Clinical (unspecified phase)
0.645	Remote Similarity	NPD7695	Clinical (unspecified phase)
0.6443	Remote Similarity	NPD5219	Approved
0.6443	Remote Similarity	NPD5218	Approved
0.6396	Remote Similarity	NPD7608	Discontinued
0.6389	Remote Similarity	NPD8416	Discontinued
0.6381	Remote Similarity	NPD7282	Approved
0.6378	Remote Similarity	NPD5265	Approved
0.6378	Remote Similarity	NPD6860	Clinical (unspecified phase)
0.6378	Remote Similarity	NPD7133	Discontinued
0.6378	Remote Similarity	NPD5264	Approved
0.6377	Remote Similarity	NPD5077	Approved
0.6377	Remote Similarity	NPD5076	Approved
0.6374	Remote Similarity	NPD4126	Approved
0.6373	Remote Similarity	NPD4557	Approved
0.6369	Remote Similarity	NPD5299	Approved
0.6359	Remote Similarity	NPD4521	Clinical (unspecified phase)
0.635	Remote Similarity	NPD8022	Clinical (unspecified phase)
0.6348	Remote Similarity	NPD4125	Approved
0.6333	Remote Similarity	NPD3659	Discontinued
0.6332	Remote Similarity	NPD8124	Phase 3
0.6332	Remote Similarity	NPD8126	Clinical (unspecified phase)
0.633	Remote Similarity	NPD5614	Approved
0.633	Remote Similarity	NPD3987	Approved
0.633	Remote Similarity	NPD5613	Approved
0.633	Remote Similarity	NPD3988	Approved
0.6328	Remote Similarity	NPD5339	Clinical (unspecified phase)
0.6321	Remote Similarity	NPD5355	Approved
0.6321	Remote Similarity	NPD5356	Approved
0.6321	Remote Similarity	NPD7811	Phase 3
0.6321	Remote Similarity	NPD7810	Phase 3
0.6319	Remote Similarity	NPD2568	Approved
0.6316	Remote Similarity	NPD7131	Phase 3
0.6308	Remote Similarity	NPD8162	Phase 2
0.6308	Remote Similarity	NPD8163	Clinical (unspecified phase)
0.6308	Remote Similarity	NPD6863	Phase 2
0.6307	Remote Similarity	NPD5367	Discontinued
0.6307	Remote Similarity	NPD3125	Approved
0.6293	Remote Similarity	NPD6557	Phase 2
0.6293	Remote Similarity	NPD6237	Clinical (unspecified phase)
0.6286	Remote Similarity	NPD2561	Approved
0.6286	Remote Similarity	NPD2562	Approved
0.6284	Remote Similarity	NPD3552	Approved
0.6284	Remote Similarity	NPD3554	Approved
0.6284	Remote Similarity	NPD3555	Approved
0.6284	Remote Similarity	NPD3553	Approved
0.6279	Remote Similarity	NPD5152	Clinical (unspecified phase)
0.6276	Remote Similarity	NPD8031	Discontinued
0.6273	Remote Similarity	NPD3879	Approved
0.627	Remote Similarity	NPD2088	Approved
0.627	Remote Similarity	NPD2087	Approved
0.6263	Remote Similarity	NPD6390	Discontinued
0.6257	Remote Similarity	NPD7979	Clinical (unspecified phase)
0.625	Remote Similarity	NPD7728	Clinical (unspecified phase)
0.625	Remote Similarity	NPD7964	Clinical (unspecified phase)
0.625	Remote Similarity	NPD7965	Phase 2
0.6237	Remote Similarity	NPD6681	Discovery
0.6231	Remote Similarity	NPD2517	Approved
0.6227	Remote Similarity	NPD3878	Approved
0.6222	Remote Similarity	NPD6919	Clinical (unspecified phase)
0.6214	Remote Similarity	NPD8255	Phase 2
0.6207	Remote Similarity	NPD5485	Approved
0.6207	Remote Similarity	NPD5484	Approved
0.6186	Remote Similarity	NPD7749	Clinical (unspecified phase)
0.6186	Remote Similarity	NPD2541	Clinical (unspecified phase)
0.6181	Remote Similarity	NPD6304	Approved
0.6181	Remote Similarity	NPD2516	Approved
0.6181	Remote Similarity	NPD6303	Approved
0.6178	Remote Similarity	NPD4186	Clinical (unspecified phase)
0.6175	Remote Similarity	NPD8643	Discontinued
0.6175	Remote Similarity	NPD4757	Clinical (unspecified phase)
0.617	Remote Similarity	NPD3400	Discontinued
0.6165	Remote Similarity	NPD7280	Phase 3
0.6165	Remote Similarity	NPD7281	Phase 3
0.615	Remote Similarity	NPD6119	Clinical (unspecified phase)
0.6146	Remote Similarity	NPD2852	Approved
0.6143	Remote Similarity	NPD6505	Approved
0.6143	Remote Similarity	NPD6504	Approved
0.6142	Remote Similarity	NPD4564	Clinical (unspecified phase)
0.6142	Remote Similarity	NPD4565	Clinical (unspecified phase)
0.6141	Remote Similarity	NPD5314	Approved
0.6141	Remote Similarity	NPD5725	Approved
0.6141	Remote Similarity	NPD6073	Approved
0.6135	Remote Similarity	NPD6853	Approved
0.6135	Remote Similarity	NPD6851	Approved
0.6127	Remote Similarity	NPD856	Approved
0.6127	Remote Similarity	NPD317	Approved
0.6127	Remote Similarity	NPD318	Approved
0.6127	Remote Similarity	NPD16	Approved
0.6126	Remote Similarity	NPD6419	Discontinued
0.6124	Remote Similarity	NPD4157	Discontinued
0.6124	Remote Similarity	NPD4435	Approved
0.6122	Remote Similarity	NPD5773	Approved
0.6122	Remote Similarity	NPD5772	Approved
0.612	Remote Similarity	NPD4153	Approved
0.6114	Remote Similarity	NPD4647	Approved
0.6114	Remote Similarity	NPD4646	Approved
0.6114	Remote Similarity	NPD4648	Approved
0.6111	Remote Similarity	NPD4175	Approved
0.6111	Remote Similarity	NPD4177	Approved
0.6111	Remote Similarity	NPD3040	Approved
0.6109	Remote Similarity	NPD2853	Approved
0.6102	Remote Similarity	NPD3071	Approved
0.6102	Remote Similarity	NPD3072	Approved
0.6102	Remote Similarity	NPD3073	Approved
0.6099	Remote Similarity	NPD597	Approved
0.6099	Remote Similarity	NPD598	Approved
0.6099	Remote Similarity	NPD601	Approved
0.6098	Remote Similarity	NPD6297	Approved
0.6096	Remote Similarity	NPD2022	Approved
0.6095	Remote Similarity	NPD6836	Approved
0.6094	Remote Similarity	NPD5230	Approved
0.6094	Remote Similarity	NPD5229	Approved
0.6091	Remote Similarity	NPD7494	Clinical (unspecified phase)
0.6087	Remote Similarity	NPD7113	Clinical (unspecified phase)
0.6085	Remote Similarity	NPD6676	Phase 2
0.6077	Remote Similarity	NPD3919	Approved
0.6077	Remote Similarity	NPD5263	Approved
0.6077	Remote Similarity	NPD4676	Approved
0.6077	Remote Similarity	NPD4434	Approved
0.6073	Remote Similarity	NPD2016	Approved
0.6073	Remote Similarity	NPD2014	Approved
0.6073	Remote Similarity	NPD2013	Approved
0.6068	Remote Similarity	NPD4087	Phase 2
0.6068	Remote Similarity	NPD5192	Clinical (unspecified phase)
0.6066	Remote Similarity	NPD1136	Approved
0.6066	Remote Similarity	NPD1132	Approved
0.6066	Remote Similarity	NPD1130	Approved
0.6066	Remote Similarity	NPD7283	Approved
0.6061	Remote Similarity	NPD4086	Phase 1
0.6058	Remote Similarity	NPD6556	Clinical (unspecified phase)
0.6056	Remote Similarity	NPD599	Approved
0.6056	Remote Similarity	NPD7451	Discontinued
0.6056	Remote Similarity	NPD602	Approved
0.6054	Remote Similarity	NPD7827	Phase 1
0.6051	Remote Similarity	NPD2891	Approved
0.6048	Remote Similarity	NPD5851	Approved
0.6048	Remote Similarity	NPD5852	Approved
0.6045	Remote Similarity	NPD4762	Approved
0.6045	Remote Similarity	NPD4761	Approved
0.6044	Remote Similarity	NPD21	Approved
0.6044	Remote Similarity	NPD2047	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