NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	3393.46
Volume:	3248.448
LogP:	0.373
LogD:	3.08
LogS:	0.567
# Rotatable Bonds:	44
TPSA:	1349.67
# H-Bond Aceptor:	80
# H-Bond Donor:	47
# Rings:	12
# Heavy Atoms:	86

MedChem Properties

QED Drug-Likeness Score:	0.006
Synthetic Accessibility Score:	10
Fsp3:	0.608
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	2
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	1.31
MDCK Permeability:	0.011403807
Pgp-inhibitor:	0
Pgp-substrate:	1
Human Intestinal Absorption (HIA):	1
20% Bioavailability (F20%):	0.999
30% Bioavailability (F30%):	0.998

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	1
Plasma Protein Binding (PPB):	24.83%
Volume Distribution (VD):	-1.648
Pgp-substrate:	81.73%

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):	-5.771
Half-life (T1/2):	0.623

ADMET: Toxicity

hERG Blockers:	0
Human Hepatotoxicity (H-HT):	1
Drug-inuced Liver Injury (DILI):	0.989
AMES Toxicity:	0
Rat Oral Acute Toxicity:	0
Maximum Recommended Daily Dose:	0.002
Skin Sensitization:	0.775
Carcinogencity:	0.027
Eye Corrosion:	0.003
Eye Irritation:	0.016
Respiratory Toxicity:	0.924

Download Data

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

Natural Product: NPC477634

Natural Product ID:	NPC477634
*Common Name:**	Circulin E
IUPAC Name:	n.a.
Synonyms:	Circulin E
Standard InCHIKey:	OQFFATFPYICMLY-WHBDPGKYSA-N
Standard InCHI:	InChI=1S/C148H220N38O42S6/c1-14-75(11)117-147(227)185-49-27-36-106(185)141(221)176-100-64-229-230-66-102-136(216)161-85(33-21-24-46-149)121(201)173-101-65-231-234-69-105(175-134(214)98(62-187)171-122(202)88(42-44-111(194)195)158-110(193)61-156-120(100)200)140(220)181-115(73(7)8)144(224)170-93(54-80-59-155-84-32-20-19-31-83(80)84)133(213)183-118(76(12)15-2)148(228)186-50-28-37-107(186)142(222)177-103(138(218)163-90(51-71(3)4)132(212)184-119(77(13)189)146(226)172-99(63-188)135(215)180-114(72(5)6)143(223)169-92(52-78-29-17-16-18-30-78)127(207)167-96(57-109(153)192)130(210)174-102)67-232-233-68-104(178-145(225)116(74(9)10)179-124(204)86(34-22-25-47-150)159-129(209)95(56-108(152)191)166-123(203)89(162-137(101)217)43-45-112(196)197)139(219)164-91(53-79-38-40-82(190)41-39-79)126(206)165-94(55-81-60-154-70-157-81)128(208)168-97(58-113(198)199)131(211)160-87(125(205)182-117)35-23-26-48-151/h16-20,29-32,38-41,59-60,70-77,85-107,114-119,155,187-190H,14-15,21-28,33-37,42-58,61-69,149-151H2,1-13H3,(H2,152,191)(H2,153,192)(H,154,157)(H,156,200)(H,158,193)(H,159,209)(H,160,211)(H,161,216)(H,162,217)(H,163,218)(H,164,219)(H,165,206)(H,166,203)(H,167,207)(H,168,208)(H,169,223)(H,170,224)(H,171,202)(H,172,226)(H,173,201)(H,174,210)(H,175,214)(H,176,221)(H,177,222)(H,178,225)(H,179,204)(H,180,215)(H,181,220)(H,182,205)(H,183,213)(H,184,212)(H,194,195)(H,196,197)(H,198,199)/t75-,76-,77+,85-,86-,87-,88-,89-,90-,91-,92-,93-,94-,95-,96-,97-,98-,99-,100-,101-,102-,103-,104-,105-,106-,107-,114-,115-,116-,117-,118-,119-/m0/s1
SMILES:	CC[C@H](C)[C@H]1C(=O)N2CCC[C@H]2C(=N[C@H]2CSSC[C@H]3C(=N[C@@H](CCCCN)C(=N[C@H]4CSSC[C@@H](C(=N[C@@H](C(C)C)C(=N[C@@H](Cc5c[nH]c6ccccc56)C(=N[C@@H]([C@@H](C)CC)C(=O)N5CCC[C@H]5C(=N[C@@H](CSSC[C@@H](C(=N[C@@H](Cc5ccc(cc5)O)C(=N[C@@H](Cc5cnc[nH]5)C(=N[C@@H](CC(=O)O)C(=N[C@@H](CCCCN)C(=N1)O)O)O)O)O)N=C([C@H](C(C)C)N=C([C@H](CCCCN)N=C([C@H](CC(=N)O)N=C([C@H](CCC(=O)O)N=C4O)O)O)O)O)C(=N[C@@H](CC(C)C)C(=N[C@@H]([C@@H](C)O)C(=N[C@@H](CO)C(=N[C@@H](C(C)C)C(=N[C@@H](Cc1ccccc1)C(=N[C@@H](CC(=N)O)C(=N3)O)O)O)O)O)O)O)O)O)O)O)N=C([C@H](CO)N=C([C@H](CCC(=O)O)N=C(CN=C2O)O)O)O)O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL508235
PubChem CID:	44575207
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
NPO40066	Chassalia parvifolia	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10691702]
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	14
IC50	1

Activity Type	# Activity
Organism	15

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	=	50.0	nM	PMID[502742]
NPT24	Organism	Human immunodeficiency virus 1	Human immunodeficiency virus 1	EC50	=	50.0	nM	PMID[502743]
NPT24	Organism	Human immunodeficiency virus 1	Human immunodeficiency virus 1	EC50	=	40.0	nM	PMID[502744]
NPT24	Organism	Human immunodeficiency virus 1	Human immunodeficiency virus 1	EC50	=	40.0	nM	PMID[502745]
NPT24	Organism	Human immunodeficiency virus 1	Human immunodeficiency virus 1	IC50	=	500.0	nM	PMID[502745]

☑ 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 NPC477634 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	524
0.1-0.2	3329
0.2-0.3	14160
0.3-0.4	17079
0.4-0.5	3652
0.5-0.6	2940
0.6-0.7	863
0.7-0.8	109
0.8-0.85	22
0.85-0.9	14
0.9-0.95	2
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9163	High Similarity	NPC477635
0.9163	High Similarity	NPC477630
0.9134	High Similarity	NPC477633
0.8039	Intermediate Similarity	NPC153400
0.7992	Intermediate Similarity	NPC28945
0.7903	Intermediate Similarity	NPC328924
0.7799	Intermediate Similarity	NPC314882
0.7742	Intermediate Similarity	NPC323244
0.7736	Intermediate Similarity	NPC314056
0.7729	Intermediate Similarity	NPC220852
0.7708	Intermediate Similarity	NPC285343
0.7683	Intermediate Similarity	NPC473317
0.7667	Intermediate Similarity	NPC478011
0.7649	Intermediate Similarity	NPC478013
0.7638	Intermediate Similarity	NPC314176
0.761	Intermediate Similarity	NPC326363
0.761	Intermediate Similarity	NPC69843
0.759	Intermediate Similarity	NPC125597
0.7588	Intermediate Similarity	NPC295452
0.7588	Intermediate Similarity	NPC171393
0.7575	Intermediate Similarity	NPC315467
0.756	Intermediate Similarity	NPC319232
0.756	Intermediate Similarity	NPC24370
0.7559	Intermediate Similarity	NPC325976
0.7547	Intermediate Similarity	NPC478006
0.7537	Intermediate Similarity	NPC478012
0.7531	Intermediate Similarity	NPC320968
0.7481	Intermediate Similarity	NPC478009
0.748	Intermediate Similarity	NPC64216
0.7409	Intermediate Similarity	NPC321939
0.7383	Intermediate Similarity	NPC323752
0.7353	Intermediate Similarity	NPC478010
0.7326	Intermediate Similarity	NPC478028
0.7276	Intermediate Similarity	NPC89987
0.7269	Intermediate Similarity	NPC478029
0.7222	Intermediate Similarity	NPC74619
0.7218	Intermediate Similarity	NPC75634
0.7189	Intermediate Similarity	NPC54744
0.7189	Intermediate Similarity	NPC282247
0.7171	Intermediate Similarity	NPC238945
0.7153	Intermediate Similarity	NPC263117
0.7153	Intermediate Similarity	NPC242872
0.7153	Intermediate Similarity	NPC125181
0.7122	Intermediate Similarity	NPC63109
0.7113	Intermediate Similarity	NPC477631
0.7095	Intermediate Similarity	NPC477639
0.7082	Intermediate Similarity	NPC214142
0.7077	Intermediate Similarity	NPC54803
0.7077	Intermediate Similarity	NPC321592
0.7073	Intermediate Similarity	NPC473376
0.7066	Intermediate Similarity	NPC95240
0.7066	Intermediate Similarity	NPC322135
0.7066	Intermediate Similarity	NPC223409
0.7061	Intermediate Similarity	NPC155143
0.7057	Intermediate Similarity	NPC39092
0.7054	Intermediate Similarity	NPC261251
0.7029	Intermediate Similarity	NPC477636
0.7028	Intermediate Similarity	NPC107077
0.7028	Intermediate Similarity	NPC223791
0.7027	Intermediate Similarity	NPC100547
0.702	Intermediate Similarity	NPC475506
0.7008	Intermediate Similarity	NPC281049
0.7008	Intermediate Similarity	NPC100321
0.7008	Intermediate Similarity	NPC293917
0.6988	Remote Similarity	NPC124920
0.6988	Remote Similarity	NPC304307
0.6988	Remote Similarity	NPC118559
0.6988	Remote Similarity	NPC34580
0.6985	Remote Similarity	NPC284888
0.6973	Remote Similarity	NPC14288
0.696	Remote Similarity	NPC162860
0.6957	Remote Similarity	NPC478157
0.6948	Remote Similarity	NPC323927
0.6947	Remote Similarity	NPC165743
0.692	Remote Similarity	NPC63279
0.6914	Remote Similarity	NPC477638
0.6914	Remote Similarity	NPC477632
0.6909	Remote Similarity	NPC150447
0.6908	Remote Similarity	NPC477177
0.6908	Remote Similarity	NPC475969
0.6908	Remote Similarity	NPC474877
0.6908	Remote Similarity	NPC475859
0.6898	Remote Similarity	NPC473640
0.6894	Remote Similarity	NPC297642
0.6892	Remote Similarity	NPC478158
0.688	Remote Similarity	NPC54420
0.6877	Remote Similarity	NPC75726
0.6877	Remote Similarity	NPC31385
0.6877	Remote Similarity	NPC110602
0.687	Remote Similarity	NPC477175
0.687	Remote Similarity	NPC470730
0.687	Remote Similarity	NPC477176
0.687	Remote Similarity	NPC470729
0.6856	Remote Similarity	NPC323198
0.6838	Remote Similarity	NPC54981
0.6832	Remote Similarity	NPC156003
0.683	Remote Similarity	NPC33064
0.683	Remote Similarity	NPC245055
0.6816	Remote Similarity	NPC82472
0.6816	Remote Similarity	NPC41679
0.6808	Remote Similarity	NPC130570
0.6796	Remote Similarity	NPC77101
0.6794	Remote Similarity	NPC476491
0.6794	Remote Similarity	NPC244536
0.6783	Remote Similarity	NPC315804
0.6783	Remote Similarity	NPC313804
0.6761	Remote Similarity	NPC171317
0.6744	Remote Similarity	NPC264285
0.6736	Remote Similarity	NPC477637
0.6733	Remote Similarity	NPC470500
0.6733	Remote Similarity	NPC179896
0.6721	Remote Similarity	NPC156704
0.672	Remote Similarity	NPC476874
0.6719	Remote Similarity	NPC229348
0.6719	Remote Similarity	NPC71238
0.6708	Remote Similarity	NPC213629
0.6706	Remote Similarity	NPC242923
0.6705	Remote Similarity	NPC16352
0.6705	Remote Similarity	NPC79386
0.6704	Remote Similarity	NPC81175
0.668	Remote Similarity	NPC471603
0.668	Remote Similarity	NPC316403
0.6679	Remote Similarity	NPC477549
0.6679	Remote Similarity	NPC473312
0.6667	Remote Similarity	NPC6215
0.6667	Remote Similarity	NPC5145
0.6655	Remote Similarity	NPC117980
0.6654	Remote Similarity	NPC184225
0.6654	Remote Similarity	NPC250178
0.6653	Remote Similarity	NPC193761
0.6643	Remote Similarity	NPC41982
0.664	Remote Similarity	NPC315491
0.664	Remote Similarity	NPC45459
0.6631	Remote Similarity	NPC475746
0.6617	Remote Similarity	NPC272549
0.6606	Remote Similarity	NPC178858
0.6605	Remote Similarity	NPC477861
0.6602	Remote Similarity	NPC74969
0.6593	Remote Similarity	NPC477107
0.6593	Remote Similarity	NPC477108
0.6593	Remote Similarity	NPC477109
0.6586	Remote Similarity	NPC77555
0.657	Remote Similarity	NPC181081
0.6568	Remote Similarity	NPC470784
0.6557	Remote Similarity	NPC17487
0.6557	Remote Similarity	NPC201831
0.6552	Remote Similarity	NPC303658
0.6549	Remote Similarity	NPC88008
0.6548	Remote Similarity	NPC300183
0.6546	Remote Similarity	NPC329295
0.6541	Remote Similarity	NPC186351
0.654	Remote Similarity	NPC474896
0.654	Remote Similarity	NPC60621
0.6535	Remote Similarity	NPC475070
0.6534	Remote Similarity	NPC478030
0.653	Remote Similarity	NPC160666
0.653	Remote Similarity	NPC476451
0.6529	Remote Similarity	NPC472789
0.6528	Remote Similarity	NPC19170
0.6522	Remote Similarity	NPC471891
0.6517	Remote Similarity	NPC33949
0.6515	Remote Similarity	NPC31097
0.6513	Remote Similarity	NPC304926
0.6513	Remote Similarity	NPC476041
0.6511	Remote Similarity	NPC14812
0.6506	Remote Similarity	NPC207686
0.6502	Remote Similarity	NPC272174
0.6491	Remote Similarity	NPC476817
0.6489	Remote Similarity	NPC477714
0.6482	Remote Similarity	NPC54537
0.6475	Remote Similarity	NPC470731
0.6475	Remote Similarity	NPC470732
0.6471	Remote Similarity	NPC15801
0.6471	Remote Similarity	NPC184680
0.6458	Remote Similarity	NPC182222
0.6455	Remote Similarity	NPC297862
0.6447	Remote Similarity	NPC470785
0.6443	Remote Similarity	NPC213308
0.6437	Remote Similarity	NPC32771
0.6431	Remote Similarity	NPC476098
0.6426	Remote Similarity	NPC477420
0.6426	Remote Similarity	NPC469594
0.6426	Remote Similarity	NPC324149
0.6426	Remote Similarity	NPC473310
0.6426	Remote Similarity	NPC477418
0.6426	Remote Similarity	NPC99666
0.6423	Remote Similarity	NPC151976
0.6423	Remote Similarity	NPC94752
0.6423	Remote Similarity	NPC87856
0.6415	Remote Similarity	NPC2395
0.6414	Remote Similarity	NPC242209
0.6412	Remote Similarity	NPC204491
0.6412	Remote Similarity	NPC132211
0.6412	Remote Similarity	NPC330009
0.6412	Remote Similarity	NPC471192
0.6412	Remote Similarity	NPC203614
0.6404	Remote Similarity	NPC235885
0.6402	Remote Similarity	NPC74360
0.6402	Remote Similarity	NPC308906
0.6398	Remote Similarity	NPC471080

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 NPC477634 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	225
0.1-0.2	634
0.2-0.3	1011
0.3-0.4	2151
0.4-0.5	2614
0.5-0.6	1928
0.6-0.7	567
0.7-0.8	20
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
0.7959	Intermediate Similarity	NPD8292	Phase 2
0.7439	Intermediate Similarity	NPD7970	Approved
0.7439	Intermediate Similarity	NPD7971	Clinical (unspecified phase)
0.7349	Intermediate Similarity	NPD8405	Clinical (unspecified phase)
0.7266	Intermediate Similarity	NPD8421	Discontinued
0.7086	Intermediate Similarity	NPD7689	Approved
0.7085	Intermediate Similarity	NPD8493	Clinical (unspecified phase)
0.7069	Intermediate Similarity	NPD8524	Approved
0.7036	Intermediate Similarity	NPD8406	Clinical (unspecified phase)
0.7028	Intermediate Similarity	NPD8525	Approved
0.7012	Intermediate Similarity	NPD8458	Clinical (unspecified phase)
0.7008	Intermediate Similarity	NPD7621	Clinical (unspecified phase)
0.7004	Intermediate Similarity	NPD8272	Phase 2
0.6984	Remote Similarity	NPD8488	Clinical (unspecified phase)
0.695	Remote Similarity	NPD7711	Discontinued
0.6948	Remote Similarity	NPD8410	Clinical (unspecified phase)
0.6932	Remote Similarity	NPD7809	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD8442	Discontinued
0.6914	Remote Similarity	NPD537	Phase 2
0.6914	Remote Similarity	NPD534	Phase 2
0.6902	Remote Similarity	NPD7980	Clinical (unspecified phase)
0.6902	Remote Similarity	NPD8271	Discontinued
0.6898	Remote Similarity	NPD8255	Phase 2
0.6882	Remote Similarity	NPD8119	Discontinued
0.6838	Remote Similarity	NPD7470	Discontinued
0.682	Remote Similarity	NPD8075	Discontinued
0.682	Remote Similarity	NPD7603	Discontinued
0.6798	Remote Similarity	NPD7465	Suspended
0.6796	Remote Similarity	NPD7655	Discontinued
0.6794	Remote Similarity	NPD6165	Phase 2
0.6794	Remote Similarity	NPD6164	Phase 2
0.6794	Remote Similarity	NPD4086	Phase 1
0.679	Remote Similarity	NPD8375	Approved
0.677	Remote Similarity	NPD8256	Approved
0.677	Remote Similarity	NPD8258	Clinical (unspecified phase)
0.677	Remote Similarity	NPD8257	Approved
0.674	Remote Similarity	NPD8371	Clinical (unspecified phase)
0.6732	Remote Similarity	NPD8261	Discontinued
0.6721	Remote Similarity	NPD7948	Phase 1
0.6711	Remote Similarity	NPD8310	Clinical (unspecified phase)
0.6706	Remote Similarity	NPD8013	Clinical (unspecified phase)
0.6703	Remote Similarity	NPD8250	Phase 2
0.6693	Remote Similarity	NPD8072	Approved
0.668	Remote Similarity	NPD796	Phase 2
0.6667	Remote Similarity	NPD8284	Discontinued
0.6667	Remote Similarity	NPD4080	Discontinued
0.6667	Remote Similarity	NPD8169	Discontinued
0.6654	Remote Similarity	NPD3042	Approved
0.6654	Remote Similarity	NPD3043	Approved
0.6643	Remote Similarity	NPD5116	Phase 1
0.6643	Remote Similarity	NPD5018	Phase 3
0.664	Remote Similarity	NPD484	Approved
0.6618	Remote Similarity	NPD6473	Phase 1
0.6618	Remote Similarity	NPD7860	Clinical (unspecified phase)
0.6608	Remote Similarity	NPD7273	Clinical (unspecified phase)
0.66	Remote Similarity	NPD3814	Phase 1
0.6588	Remote Similarity	NPD7981	Discontinued
0.6587	Remote Similarity	NPD8073	Approved
0.6584	Remote Similarity	NPD7923	Phase 2
0.6583	Remote Similarity	NPD8370	Discontinued
0.658	Remote Similarity	NPD6970	Phase 2
0.6577	Remote Similarity	NPD7823	Clinical (unspecified phase)
0.6576	Remote Similarity	NPD949	Phase 1
0.6575	Remote Similarity	NPD6403	Clinical (unspecified phase)
0.6569	Remote Similarity	NPD3959	Phase 2
0.6569	Remote Similarity	NPD3962	Phase 2
0.6564	Remote Similarity	NPD8112	Clinical (unspecified phase)
0.6558	Remote Similarity	NPD4558	Phase 2
0.655	Remote Similarity	NPD2794	Discontinued
0.655	Remote Similarity	NPD7594	Clinical (unspecified phase)
0.6549	Remote Similarity	NPD8322	Phase 2
0.6547	Remote Similarity	NPD6724	Clinical (unspecified phase)
0.6545	Remote Similarity	NPD8291	Clinical (unspecified phase)
0.6541	Remote Similarity	NPD8430	Approved
0.653	Remote Similarity	NPD8316	Phase 2
0.653	Remote Similarity	NPD5935	Discontinued
0.653	Remote Similarity	NPD8317	Phase 2
0.6526	Remote Similarity	NPD4442	Phase 2
0.6515	Remote Similarity	NPD8356	Approved
0.6506	Remote Similarity	NPD3960	Clinical (unspecified phase)
0.65	Remote Similarity	NPD4438	Approved
0.6498	Remote Similarity	NPD6545	Clinical (unspecified phase)
0.6498	Remote Similarity	NPD8349	Phase 1
0.6498	Remote Similarity	NPD6351	Discovery
0.6496	Remote Similarity	NPD3914	Clinical (unspecified phase)
0.6494	Remote Similarity	NPD24	Approved
0.6491	Remote Similarity	NPD8287	Phase 1
0.6491	Remote Similarity	NPD8288	Phase 2
0.6487	Remote Similarity	NPD6742	Phase 2
0.6487	Remote Similarity	NPD6743	Phase 2
0.6486	Remote Similarity	NPD7486	Phase 1
0.6486	Remote Similarity	NPD3917	Approved
0.6486	Remote Similarity	NPD3916	Clinical (unspecified phase)
0.6486	Remote Similarity	NPD3918	Approved
0.6484	Remote Similarity	NPD7834	Approved
0.6484	Remote Similarity	NPD7117	Phase 2
0.6482	Remote Similarity	NPD8629	Discontinued
0.6481	Remote Similarity	NPD7415	Suspended
0.6477	Remote Similarity	NPD4414	Discontinued
0.6477	Remote Similarity	NPD8484	Phase 2
0.6471	Remote Similarity	NPD7712	Clinical (unspecified phase)
0.6464	Remote Similarity	NPD4555	Clinical (unspecified phase)
0.6464	Remote Similarity	NPD8105	Discontinued
0.6462	Remote Similarity	NPD7898	Clinical (unspecified phase)
0.6462	Remote Similarity	NPD7897	Phase 3
0.6459	Remote Similarity	NPD4612	Discontinued
0.6453	Remote Similarity	NPD6824	Clinical (unspecified phase)
0.6452	Remote Similarity	NPD459	Clinical (unspecified phase)
0.645	Remote Similarity	NPD2812	Clinical (unspecified phase)
0.645	Remote Similarity	NPD2813	Phase 3
0.6448	Remote Similarity	NPD3915	Approved
0.6445	Remote Similarity	NPD7957	Phase 1
0.6445	Remote Similarity	NPD7958	Clinical (unspecified phase)
0.6441	Remote Similarity	NPD8247	Approved
0.6441	Remote Similarity	NPD8246	Approved
0.6429	Remote Similarity	NPD7553	Discontinued
0.6423	Remote Similarity	NPD6992	Phase 2
0.6421	Remote Similarity	NPD25	Approved
0.6421	Remote Similarity	NPD5461	Discontinued
0.6421	Remote Similarity	NPD26	Approved
0.642	Remote Similarity	NPD6838	Clinical (unspecified phase)
0.6418	Remote Similarity	NPD8049	Phase 2
0.6417	Remote Similarity	NPD7903	Clinical (unspecified phase)
0.6416	Remote Similarity	NPD7181	Phase 3
0.6413	Remote Similarity	NPD7068	Approved
0.6413	Remote Similarity	NPD7067	Approved
0.6412	Remote Similarity	NPD7112	Discontinued
0.6411	Remote Similarity	NPD6023	Discontinued
0.6409	Remote Similarity	NPD8321	Discontinued
0.6398	Remote Similarity	NPD8094	Discontinued
0.6397	Remote Similarity	NPD3002	Clinical (unspecified phase)
0.6397	Remote Similarity	NPD6142	Phase 3
0.6395	Remote Similarity	NPD2442	Approved
0.6395	Remote Similarity	NPD2443	Approved
0.6389	Remote Similarity	NPD2880	Discontinued
0.6377	Remote Similarity	NPD7770	Phase 3
0.6377	Remote Similarity	NPD6856	Discontinued
0.6376	Remote Similarity	NPD3343	Phase 3
0.6375	Remote Similarity	NPD7944	Discontinued
0.6371	Remote Similarity	NPD8110	Clinical (unspecified phase)
0.6367	Remote Similarity	NPD6752	Phase 1
0.6367	Remote Similarity	NPD6753	Phase 1
0.6367	Remote Similarity	NPD7202	Clinical (unspecified phase)
0.636	Remote Similarity	NPD994	Phase 2
0.636	Remote Similarity	NPD8093	Discontinued
0.636	Remote Similarity	NPD996	Phase 2
0.6357	Remote Similarity	NPD7730	Approved
0.6357	Remote Similarity	NPD7731	Approved
0.6353	Remote Similarity	NPD7726	Phase 1
0.6349	Remote Similarity	NPD8253	Phase 3
0.6348	Remote Similarity	NPD7198	Clinical (unspecified phase)
0.6346	Remote Similarity	NPD5072	Discontinued
0.6346	Remote Similarity	NPD3014	Clinical (unspecified phase)
0.6346	Remote Similarity	NPD3013	Phase 3
0.6344	Remote Similarity	NPD7996	Phase 2
0.6341	Remote Similarity	NPD2096	Phase 2
0.6341	Remote Similarity	NPD2091	Phase 2
0.6337	Remote Similarity	NPD3838	Phase 3
0.6336	Remote Similarity	NPD7557	Clinical (unspecified phase)
0.6335	Remote Similarity	NPD5575	Clinical (unspecified phase)
0.6332	Remote Similarity	NPD7947	Clinical (unspecified phase)
0.6331	Remote Similarity	NPD5483	Clinical (unspecified phase)
0.6329	Remote Similarity	NPD7706	Clinical (unspecified phase)
0.6324	Remote Similarity	NPD5015	Clinical (unspecified phase)
0.6323	Remote Similarity	NPD5509	Phase 1
0.6318	Remote Similarity	NPD7856	Phase 2
0.6318	Remote Similarity	NPD7857	Phase 3
0.631	Remote Similarity	NPD8641	Approved
0.631	Remote Similarity	NPD8364	Approved
0.631	Remote Similarity	NPD8363	Approved
0.631	Remote Similarity	NPD7824	Approved
0.6308	Remote Similarity	NPD5807	Phase 2
0.6301	Remote Similarity	NPD2095	Phase 2
0.6301	Remote Similarity	NPD2094	Phase 2
0.6301	Remote Similarity	NPD2092	Phase 2
0.6299	Remote Similarity	NPD5482	Discontinued
0.6299	Remote Similarity	NPD7769	Phase 3
0.6298	Remote Similarity	NPD8096	Phase 3
0.6298	Remote Similarity	NPD8097	Phase 3
0.6296	Remote Similarity	NPD7929	Approved
0.6296	Remote Similarity	NPD7928	Approved
0.6295	Remote Similarity	NPD2127	Suspended
0.6295	Remote Similarity	NPD4440	Clinical (unspecified phase)
0.6295	Remote Similarity	NPD6665	Discontinued
0.6293	Remote Similarity	NPD7544	Discontinued
0.6291	Remote Similarity	NPD5920	Clinical (unspecified phase)
0.6288	Remote Similarity	NPD3353	Approved
0.6288	Remote Similarity	NPD6643	Discontinued
0.6288	Remote Similarity	NPD5612	Discontinued
0.6285	Remote Similarity	NPD6456	Discontinued
0.6285	Remote Similarity	NPD7818	Clinical (unspecified phase)
0.6283	Remote Similarity	NPD7271	Approved
0.6282	Remote Similarity	NPD3872	Phase 3
0.6282	Remote Similarity	NPD6848	Phase 1
0.628	Remote Similarity	NPD1043	Phase 3
0.6279	Remote Similarity	NPD5426	Phase 3
0.6279	Remote Similarity	NPD8098	Approved
0.6279	Remote Similarity	NPD3500	Clinical (unspecified phase)
0.6277	Remote Similarity	NPD7502	Clinical (unspecified phase)
0.6273	Remote Similarity	NPD1571	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