NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	3457.45
Volume:	3309.957
LogP:	0.293
LogD:	3.275
LogS:	0.487
# Rotatable Bonds:	45
TPSA:	1369.9
# H-Bond Aceptor:	81
# H-Bond Donor:	48
# Rings:	13
# Heavy Atoms:	87

MedChem Properties

QED Drug-Likeness Score:	0.006
Synthetic Accessibility Score:	10
Fsp3:	0.579
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:	1.027
MDCK Permeability:	0.006972256
Pgp-inhibitor:	0
Pgp-substrate:	1
Human Intestinal Absorption (HIA):	1
20% Bioavailability (F20%):	1
30% Bioavailability (F30%):	1

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	1
Plasma Protein Binding (PPB):	27.17%
Volume Distribution (VD):	-1.628
Pgp-substrate:	91.97%

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):	-6.15
Half-life (T1/2):	0.665

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:	0.004
Skin Sensitization:	0.794
Carcinogencity:	0.044
Eye Corrosion:	0.003
Eye Irritation:	0.013
Respiratory Toxicity:	0.852

Download Data

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

Natural Product: NPC477633

Natural Product ID:	NPC477633
*Common Name:**	Circulin D
IUPAC Name:	n.a.
Synonyms:	Circulin D
Standard InCHIKey:	MSVJOJFCJSDVQL-BDXIEVRTSA-N
Standard InCHI:	InChI=1S/C152H220N38O43S6/c1-12-76(8)120-149(230)173-95(54-80-28-16-15-17-29-80)131(212)171-100(60-113(157)197)134(215)178-106-69-235-234-67-104-124(205)160-64-114(198)162-92(45-47-115(199)200)126(207)175-102(65-191)138(219)179-109-72-239-236-68-105(177-125(206)89(165-140(106)221)32-20-23-49-153)141(222)166-93(46-48-116(201)202)127(208)170-99(59-112(156)196)133(214)163-90(33-21-24-50-154)128(209)183-119(75(6)7)148(229)182-108(143(224)167-94(55-81-37-41-85(194)42-38-81)130(211)169-98(58-84-63-158-73-161-84)132(213)172-101(61-117(203)204)135(216)164-91(34-22-25-51-155)129(210)186-121(77(9)13-2)151(232)189-52-26-35-110(189)145(226)180-104)71-238-237-70-107(142(223)168-96(56-82-39-43-86(195)44-40-82)136(217)188-123(79(11)193)150(231)176-103(66-192)139(220)185-120)181-146(227)111-36-27-53-190(111)152(233)122(78(10)14-3)187-137(218)97(174-147(228)118(74(4)5)184-144(109)225)57-83-62-159-88-31-19-18-30-87(83)88/h15-19,28-31,37-44,62-63,73-79,89-111,118-123,159,191-195H,12-14,20-27,32-36,45-61,64-72,153-155H2,1-11H3,(H2,156,196)(H2,157,197)(H,158,161)(H,160,205)(H,162,198)(H,163,214)(H,164,216)(H,165,221)(H,166,222)(H,167,224)(H,168,223)(H,169,211)(H,170,208)(H,171,212)(H,172,213)(H,173,230)(H,174,228)(H,175,207)(H,176,231)(H,177,206)(H,178,215)(H,179,219)(H,180,226)(H,181,227)(H,182,229)(H,183,209)(H,184,225)(H,185,220)(H,186,210)(H,187,218)(H,188,217)(H,199,200)(H,201,202)(H,203,204)/t76-,77-,78-,79+,89-,90-,91-,92-,93-,94-,95-,96-,97-,98-,99-,100-,101-,102-,103-,104-,105-,106-,107-,108-,109-,110-,111-,118-,119-,120-,121-,122-,123-/m0/s1
SMILES:	NCCCC[C@@H]1N=C(O)[C@H](CC(=O)O)N=C(O)[C@H](Cc2[nH]cnc2)N=C(O)[C@H](Cc2ccc(cc2)O)N=C(O)[C@@H]2CSSC[C@@H]3N=C(O)[C@@H]4CCCN4C(=O)[C@@H](N=C(O)[C@@H](N=C([C@@H](N=C([C@H]4N=C([C@@H](N=C([C@@H](N=C(CN=C([C@@H](N=C([C@H]5N(C(=O)[C@@H](N=C1O)[C@H](CC)C)CCC5)O)CSSC[C@H](N=C(O)[C@H](CC(=N)O)N=C(O)[C@H](Cc1ccccc1)N=C(O)[C@@H](N=C([C@@H](N=C([C@@H](N=C([C@@H](N=C3O)Cc1ccc(cc1)O)O)[C@H](O)C)O)CO)O)[C@H](CC)C)C(=N[C@@H](CCCCN)C(=N[C@@H](CSSC4)C(=N[C@H](C(=N[C@H](C(=N[C@H](C(=N[C@H](C(=N2)O)C(C)C)O)CCCCN)O)CC(=N)O)O)CCC(=O)O)O)O)O)O)O)CCC(=O)O)O)CO)O)O)C(C)C)O)Cc1c[nH]c2c1cccc2)[C@H](CC)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL448022
PubChem CID:	44593582
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[485421]
NPT24	Organism	Human immunodeficiency virus 1	Human immunodeficiency virus 1	EC50	=	50.0	nM	PMID[485422]
NPT24	Organism	Human immunodeficiency virus 1	Human immunodeficiency virus 1	EC50	=	40.0	nM	PMID[485423]
NPT24	Organism	Human immunodeficiency virus 1	Human immunodeficiency virus 1	EC50	=	40.0	nM	PMID[485424]
NPT24	Organism	Human immunodeficiency virus 1	Human immunodeficiency virus 1	IC50	=	500.0	nM	PMID[485424]

☑ 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 NPC477633 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	535
0.1-0.2	3286
0.2-0.3	14288
0.3-0.4	17020
0.4-0.5	3683
0.5-0.6	2908
0.6-0.7	844
0.7-0.8	98
0.8-0.85	15
0.85-0.9	16
0.9-0.95	2
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9134	High Similarity	NPC477634
0.872	High Similarity	NPC153400
0.8566	High Similarity	NPC477635
0.8566	High Similarity	NPC477630
0.8233	Intermediate Similarity	NPC325976
0.8167	Intermediate Similarity	NPC28945
0.808	Intermediate Similarity	NPC328924
0.8072	Intermediate Similarity	NPC326363
0.8072	Intermediate Similarity	NPC69843
0.7984	Intermediate Similarity	NPC478028
0.7969	Intermediate Similarity	NPC314882
0.7922	Intermediate Similarity	NPC478029
0.792	Intermediate Similarity	NPC323244
0.7917	Intermediate Similarity	NPC478006
0.7903	Intermediate Similarity	NPC314056
0.7897	Intermediate Similarity	NPC478011
0.7882	Intermediate Similarity	NPC285343
0.7868	Intermediate Similarity	NPC314176
0.7863	Intermediate Similarity	NPC473317
0.7844	Intermediate Similarity	NPC478009
0.7815	Intermediate Similarity	NPC478013
0.7807	Intermediate Similarity	NPC315467
0.7769	Intermediate Similarity	NPC125597
0.7766	Intermediate Similarity	NPC478012
0.7765	Intermediate Similarity	NPC220852
0.7761	Intermediate Similarity	NPC171393
0.7761	Intermediate Similarity	NPC295452
0.7738	Intermediate Similarity	NPC319232
0.7738	Intermediate Similarity	NPC24370
0.7712	Intermediate Similarity	NPC478010
0.7701	Intermediate Similarity	NPC321939
0.7571	Intermediate Similarity	NPC320968
0.7558	Intermediate Similarity	NPC323752
0.7546	Intermediate Similarity	NPC63109
0.754	Intermediate Similarity	NPC75634
0.752	Intermediate Similarity	NPC64216
0.749	Intermediate Similarity	NPC238945
0.7454	Intermediate Similarity	NPC74619
0.7445	Intermediate Similarity	NPC125181
0.7445	Intermediate Similarity	NPC263117
0.7445	Intermediate Similarity	NPC242872
0.7409	Intermediate Similarity	NPC323927
0.7349	Intermediate Similarity	NPC107077
0.7349	Intermediate Similarity	NPC223791
0.7318	Intermediate Similarity	NPC165743
0.7318	Intermediate Similarity	NPC89987
0.7293	Intermediate Similarity	NPC39092
0.728	Intermediate Similarity	NPC475969
0.728	Intermediate Similarity	NPC475859
0.728	Intermediate Similarity	NPC162860
0.7273	Intermediate Similarity	NPC478157
0.7259	Intermediate Similarity	NPC214142
0.7252	Intermediate Similarity	NPC321592
0.7252	Intermediate Similarity	NPC54803
0.7241	Intermediate Similarity	NPC95240
0.7241	Intermediate Similarity	NPC223409
0.7241	Intermediate Similarity	NPC477175
0.7241	Intermediate Similarity	NPC470730
0.7241	Intermediate Similarity	NPC322135
0.7233	Intermediate Similarity	NPC282247
0.7233	Intermediate Similarity	NPC54744
0.7231	Intermediate Similarity	NPC261251
0.7224	Intermediate Similarity	NPC63279
0.7214	Intermediate Similarity	NPC477177
0.7214	Intermediate Similarity	NPC474877
0.7203	Intermediate Similarity	NPC100547
0.72	Intermediate Similarity	NPC54420
0.72	Intermediate Similarity	NPC150447
0.7199	Intermediate Similarity	NPC77101
0.7197	Intermediate Similarity	NPC297642
0.7194	Intermediate Similarity	NPC110602
0.7194	Intermediate Similarity	NPC75726
0.7194	Intermediate Similarity	NPC31385
0.7188	Intermediate Similarity	NPC281049
0.7176	Intermediate Similarity	NPC477176
0.7176	Intermediate Similarity	NPC470729
0.7165	Intermediate Similarity	NPC118559
0.7165	Intermediate Similarity	NPC304307
0.7165	Intermediate Similarity	NPC124920
0.7165	Intermediate Similarity	NPC34580
0.7159	Intermediate Similarity	NPC284888
0.7148	Intermediate Similarity	NPC14288
0.712	Intermediate Similarity	NPC473376
0.7115	Intermediate Similarity	NPC130570
0.7108	Intermediate Similarity	NPC155143
0.709	Intermediate Similarity	NPC477861
0.7075	Intermediate Similarity	NPC478158
0.7068	Intermediate Similarity	NPC475506
0.7057	Intermediate Similarity	NPC117980
0.7056	Intermediate Similarity	NPC100321
0.7056	Intermediate Similarity	NPC293917
0.7052	Intermediate Similarity	NPC470500
0.704	Intermediate Similarity	NPC193761
0.703	Intermediate Similarity	NPC323198
0.702	Intermediate Similarity	NPC54981
0.7011	Intermediate Similarity	NPC477109
0.7011	Intermediate Similarity	NPC477107
0.7011	Intermediate Similarity	NPC477108
0.7004	Intermediate Similarity	NPC245055
0.7004	Intermediate Similarity	NPC33064
0.6992	Remote Similarity	NPC471603
0.6989	Remote Similarity	NPC82472
0.6989	Remote Similarity	NPC41679
0.6988	Remote Similarity	NPC477714
0.698	Remote Similarity	NPC5145
0.6974	Remote Similarity	NPC17487
0.6974	Remote Similarity	NPC201831
0.697	Remote Similarity	NPC476491
0.6964	Remote Similarity	NPC477632
0.6964	Remote Similarity	NPC477638
0.695	Remote Similarity	NPC477715
0.6948	Remote Similarity	NPC473640
0.6948	Remote Similarity	NPC171317
0.6937	Remote Similarity	NPC81175
0.6923	Remote Similarity	NPC264285
0.6914	Remote Similarity	NPC477549
0.6905	Remote Similarity	NPC476874
0.6902	Remote Similarity	NPC71238
0.6898	Remote Similarity	NPC178858
0.6894	Remote Similarity	NPC19170
0.6889	Remote Similarity	NPC15801
0.6885	Remote Similarity	NPC304926
0.6885	Remote Similarity	NPC476041
0.6882	Remote Similarity	NPC16352
0.688	Remote Similarity	NPC33949
0.688	Remote Similarity	NPC156003
0.6867	Remote Similarity	NPC329295
0.685	Remote Similarity	NPC475070
0.685	Remote Similarity	NPC473312
0.6846	Remote Similarity	NPC470731
0.6844	Remote Similarity	NPC474896
0.6842	Remote Similarity	NPC6215
0.6832	Remote Similarity	NPC315804
0.6832	Remote Similarity	NPC313804
0.6832	Remote Similarity	NPC250178
0.6827	Remote Similarity	NPC184225
0.6818	Remote Similarity	NPC31097
0.6816	Remote Similarity	NPC297862
0.6812	Remote Similarity	NPC471891
0.6809	Remote Similarity	NPC41982
0.6806	Remote Similarity	NPC272174
0.6803	Remote Similarity	NPC207686
0.6799	Remote Similarity	NPC14812
0.6797	Remote Similarity	NPC475746
0.679	Remote Similarity	NPC272549
0.6782	Remote Similarity	NPC470732
0.6782	Remote Similarity	NPC74969
0.6779	Remote Similarity	NPC186351
0.6773	Remote Similarity	NPC156704
0.6769	Remote Similarity	NPC229348
0.6761	Remote Similarity	NPC213629
0.6757	Remote Similarity	NPC242923
0.6756	Remote Similarity	NPC79386
0.6755	Remote Similarity	NPC312942
0.6755	Remote Similarity	NPC327095
0.6747	Remote Similarity	NPC477631
0.6747	Remote Similarity	NPC324149
0.6738	Remote Similarity	NPC181081
0.6729	Remote Similarity	NPC40455
0.6718	Remote Similarity	NPC183407
0.6717	Remote Similarity	NPC60621
0.6716	Remote Similarity	NPC244536
0.6704	Remote Similarity	NPC476451
0.6704	Remote Similarity	NPC160666
0.6703	Remote Similarity	NPC478030
0.6693	Remote Similarity	NPC315491
0.6693	Remote Similarity	NPC45459
0.6692	Remote Similarity	NPC27041
0.6689	Remote Similarity	NPC315499
0.6679	Remote Similarity	NPC477516
0.6679	Remote Similarity	NPC316110
0.6679	Remote Similarity	NPC276657
0.6679	Remote Similarity	NPC315893
0.6679	Remote Similarity	NPC313587
0.6679	Remote Similarity	NPC63031
0.6667	Remote Similarity	NPC477639
0.6667	Remote Similarity	NPC91868
0.6667	Remote Similarity	NPC477636
0.6667	Remote Similarity	NPC63971
0.6667	Remote Similarity	NPC229893
0.6656	Remote Similarity	NPC470900
0.6655	Remote Similarity	NPC476493
0.6654	Remote Similarity	NPC471192
0.6644	Remote Similarity	NPC260909
0.6642	Remote Similarity	NPC213530
0.6642	Remote Similarity	NPC193267
0.663	Remote Similarity	NPC191382
0.663	Remote Similarity	NPC182222
0.663	Remote Similarity	NPC56109
0.6629	Remote Similarity	NPC253987
0.6629	Remote Similarity	NPC220851
0.6629	Remote Similarity	NPC470501
0.6629	Remote Similarity	NPC155444
0.6628	Remote Similarity	NPC82370
0.6619	Remote Similarity	NPC470504
0.6618	Remote Similarity	NPC470784
0.6618	Remote Similarity	NPC101350
0.6614	Remote Similarity	NPC99666
0.6614	Remote Similarity	NPC115282
0.6613	Remote Similarity	NPC94752

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 NPC477633 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	228
0.1-0.2	645
0.2-0.3	1024
0.3-0.4	2171
0.4-0.5	2607
0.5-0.6	1910
0.6-0.7	544
0.7-0.8	21
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
0.7992	Intermediate Similarity	NPD8292	Phase 2
0.7774	Intermediate Similarity	NPD8524	Approved
0.7679	Intermediate Similarity	NPD8525	Approved
0.7671	Intermediate Similarity	NPD8405	Clinical (unspecified phase)
0.7604	Intermediate Similarity	NPD8421	Discontinued
0.754	Intermediate Similarity	NPD8458	Clinical (unspecified phase)
0.751	Intermediate Similarity	NPD8488	Clinical (unspecified phase)
0.748	Intermediate Similarity	NPD7971	Clinical (unspecified phase)
0.748	Intermediate Similarity	NPD7970	Approved
0.7374	Intermediate Similarity	NPD7689	Approved
0.7352	Intermediate Similarity	NPD8258	Clinical (unspecified phase)
0.7352	Intermediate Similarity	NPD8256	Approved
0.7352	Intermediate Similarity	NPD8406	Clinical (unspecified phase)
0.7352	Intermediate Similarity	NPD8257	Approved
0.7343	Intermediate Similarity	NPD8442	Discontinued
0.7339	Intermediate Similarity	NPD8493	Clinical (unspecified phase)
0.72	Intermediate Similarity	NPD8410	Clinical (unspecified phase)
0.7192	Intermediate Similarity	NPD7711	Discontinued
0.7186	Intermediate Similarity	NPD8119	Discontinued
0.7172	Intermediate Similarity	NPD8349	Phase 1
0.7148	Intermediate Similarity	NPD8317	Phase 2
0.7148	Intermediate Similarity	NPD8316	Phase 2
0.7131	Intermediate Similarity	NPD8322	Phase 2
0.7126	Intermediate Similarity	NPD7603	Discontinued
0.7115	Intermediate Similarity	NPD7809	Clinical (unspecified phase)
0.7095	Intermediate Similarity	NPD8310	Clinical (unspecified phase)
0.7071	Intermediate Similarity	NPD8284	Discontinued
0.7065	Intermediate Similarity	NPD8484	Phase 2
0.7059	Intermediate Similarity	NPD8250	Phase 2
0.7056	Intermediate Similarity	NPD7621	Clinical (unspecified phase)
0.7052	Intermediate Similarity	NPD8272	Phase 2
0.7045	Intermediate Similarity	NPD7948	Phase 1
0.7034	Intermediate Similarity	NPD6164	Phase 2
0.7034	Intermediate Similarity	NPD6165	Phase 2
0.702	Intermediate Similarity	NPD8013	Clinical (unspecified phase)
0.702	Intermediate Similarity	NPD7470	Discontinued
0.7016	Intermediate Similarity	NPD8271	Discontinued
0.7016	Intermediate Similarity	NPD7980	Clinical (unspecified phase)
0.6989	Remote Similarity	NPD7923	Phase 2
0.698	Remote Similarity	NPD7465	Suspended
0.6966	Remote Similarity	NPD7415	Suspended
0.6962	Remote Similarity	NPD534	Phase 2
0.6962	Remote Similarity	NPD537	Phase 2
0.6938	Remote Similarity	NPD8112	Clinical (unspecified phase)
0.6932	Remote Similarity	NPD8629	Discontinued
0.6932	Remote Similarity	NPD8075	Discontinued
0.692	Remote Similarity	NPD7181	Phase 3
0.6914	Remote Similarity	NPD8261	Discontinued
0.6912	Remote Similarity	NPD6473	Phase 1
0.6912	Remote Similarity	NPD7860	Clinical (unspecified phase)
0.6899	Remote Similarity	NPD7655	Discontinued
0.6895	Remote Similarity	NPD6724	Clinical (unspecified phase)
0.6877	Remote Similarity	NPD8072	Approved
0.6864	Remote Similarity	NPD5018	Phase 3
0.684	Remote Similarity	NPD4080	Discontinued
0.6836	Remote Similarity	NPD8375	Approved
0.6834	Remote Similarity	NPD8094	Discontinued
0.6824	Remote Similarity	NPD7958	Clinical (unspecified phase)
0.6824	Remote Similarity	NPD7957	Phase 1
0.6821	Remote Similarity	NPD8255	Phase 2
0.6821	Remote Similarity	NPD8049	Phase 2
0.682	Remote Similarity	NPD7823	Clinical (unspecified phase)
0.6809	Remote Similarity	NPD5116	Phase 1
0.6807	Remote Similarity	NPD4442	Phase 2
0.6795	Remote Similarity	NPD8093	Discontinued
0.6795	Remote Similarity	NPD7594	Clinical (unspecified phase)
0.6788	Remote Similarity	NPD3914	Clinical (unspecified phase)
0.6787	Remote Similarity	NPD8523	Approved
0.6787	Remote Similarity	NPD8371	Clinical (unspecified phase)
0.6786	Remote Similarity	NPD3814	Phase 1
0.6786	Remote Similarity	NPD8246	Approved
0.6786	Remote Similarity	NPD8247	Approved
0.6783	Remote Similarity	NPD8321	Discontinued
0.678	Remote Similarity	NPD4414	Discontinued
0.6779	Remote Similarity	NPD8430	Approved
0.6772	Remote Similarity	NPD8073	Approved
0.6772	Remote Similarity	NPD7273	Clinical (unspecified phase)
0.6772	Remote Similarity	NPD8288	Phase 2
0.6772	Remote Similarity	NPD8287	Phase 1
0.6768	Remote Similarity	NPD8105	Discontinued
0.6755	Remote Similarity	NPD8356	Approved
0.6751	Remote Similarity	NPD7996	Phase 2
0.6741	Remote Similarity	NPD3960	Clinical (unspecified phase)
0.6739	Remote Similarity	NPD3962	Phase 2
0.6739	Remote Similarity	NPD3959	Phase 2
0.6732	Remote Similarity	NPD796	Phase 2
0.6731	Remote Similarity	NPD2794	Discontinued
0.6727	Remote Similarity	NPD4558	Phase 2
0.6716	Remote Similarity	NPD4086	Phase 1
0.6716	Remote Similarity	NPD8047	Clinical (unspecified phase)
0.6715	Remote Similarity	NPD6992	Phase 2
0.6705	Remote Similarity	NPD7981	Discontinued
0.6705	Remote Similarity	NPD7947	Clinical (unspecified phase)
0.6705	Remote Similarity	NPD7557	Clinical (unspecified phase)
0.6704	Remote Similarity	NPD3042	Approved
0.6704	Remote Similarity	NPD3043	Approved
0.6703	Remote Similarity	NPD7068	Approved
0.6703	Remote Similarity	NPD7067	Approved
0.6701	Remote Similarity	NPD8363	Approved
0.6701	Remote Similarity	NPD8364	Approved
0.6693	Remote Similarity	NPD7944	Discontinued
0.6693	Remote Similarity	NPD484	Approved
0.6691	Remote Similarity	NPD6970	Phase 2
0.6678	Remote Similarity	NPD7198	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD7202	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6351	Discovery
0.6667	Remote Similarity	NPD7770	Phase 3
0.6667	Remote Similarity	NPD4438	Approved
0.6667	Remote Similarity	NPD6838	Clinical (unspecified phase)
0.6655	Remote Similarity	NPD7486	Phase 1
0.6655	Remote Similarity	NPD6742	Phase 2
0.6655	Remote Similarity	NPD8365	Clinical (unspecified phase)
0.6655	Remote Similarity	NPD6743	Phase 2
0.6654	Remote Similarity	NPD7791	Approved
0.6654	Remote Similarity	NPD3014	Clinical (unspecified phase)
0.6654	Remote Similarity	NPD7789	Approved
0.6654	Remote Similarity	NPD7998	Clinical (unspecified phase)
0.6654	Remote Similarity	NPD7712	Clinical (unspecified phase)
0.6654	Remote Similarity	NPD7790	Approved
0.6654	Remote Similarity	NPD7112	Discontinued
0.6654	Remote Similarity	NPD7952	Approved
0.6654	Remote Similarity	NPD7558	Phase 2
0.6654	Remote Similarity	NPD7730	Approved
0.6654	Remote Similarity	NPD3013	Phase 3
0.6654	Remote Similarity	NPD7950	Approved
0.6654	Remote Similarity	NPD7953	Approved
0.6654	Remote Similarity	NPD7731	Approved
0.6654	Remote Similarity	NPD7951	Approved
0.6644	Remote Similarity	NPD8460	Approved
0.6644	Remote Similarity	NPD8459	Approved
0.6642	Remote Similarity	NPD4555	Clinical (unspecified phase)
0.6641	Remote Similarity	NPD4612	Discontinued
0.6631	Remote Similarity	NPD8370	Discontinued
0.6631	Remote Similarity	NPD7898	Clinical (unspecified phase)
0.6631	Remote Similarity	NPD7897	Phase 3
0.663	Remote Similarity	NPD7780	Approved
0.663	Remote Similarity	NPD7781	Approved
0.6629	Remote Similarity	NPD8000	Clinical (unspecified phase)
0.6629	Remote Similarity	NPD2813	Phase 3
0.6629	Remote Similarity	NPD2812	Clinical (unspecified phase)
0.6629	Remote Similarity	NPD6824	Clinical (unspecified phase)
0.6628	Remote Similarity	NPD6403	Clinical (unspecified phase)
0.6619	Remote Similarity	NPD5483	Clinical (unspecified phase)
0.6608	Remote Similarity	NPD7706	Clinical (unspecified phase)
0.6606	Remote Similarity	NPD7857	Phase 3
0.6606	Remote Similarity	NPD7856	Phase 2
0.6605	Remote Similarity	NPD7824	Approved
0.6604	Remote Similarity	NPD6753	Phase 1
0.6604	Remote Similarity	NPD6752	Phase 1
0.6602	Remote Similarity	NPD7834	Approved
0.6597	Remote Similarity	NPD3343	Phase 3
0.6595	Remote Similarity	NPD5807	Phase 2
0.6595	Remote Similarity	NPD8291	Clinical (unspecified phase)
0.6594	Remote Similarity	NPD7117	Phase 2
0.6592	Remote Similarity	NPD7726	Phase 1
0.6589	Remote Similarity	NPD8169	Discontinued
0.6588	Remote Similarity	NPD8396	Approved
0.6588	Remote Similarity	NPD8395	Approved
0.6584	Remote Similarity	NPD5482	Discontinued
0.6584	Remote Similarity	NPD7769	Phase 3
0.6583	Remote Similarity	NPD4440	Clinical (unspecified phase)
0.6581	Remote Similarity	NPD8004	Discontinued
0.658	Remote Similarity	NPD7271	Approved
0.658	Remote Similarity	NPD4403	Phase 3
0.658	Remote Similarity	NPD4401	Phase 2
0.6577	Remote Similarity	NPD2442	Approved
0.6577	Remote Similarity	NPD2443	Approved
0.6575	Remote Similarity	NPD2880	Discontinued
0.6574	Remote Similarity	NPD6023	Discontinued
0.657	Remote Similarity	NPD3872	Phase 3
0.6569	Remote Similarity	NPD7502	Clinical (unspecified phase)
0.6569	Remote Similarity	NPD6142	Phase 3
0.6566	Remote Similarity	NPD7929	Approved
0.6566	Remote Similarity	NPD7928	Approved
0.6565	Remote Similarity	NPD8429	Approved
0.6565	Remote Similarity	NPD8467	Approved
0.6565	Remote Similarity	NPD8428	Approved
0.6565	Remote Similarity	NPD8465	Approved
0.6565	Remote Similarity	NPD8466	Approved
0.6565	Remote Similarity	NPD8427	Approved
0.6562	Remote Similarity	NPD5949	Phase 3
0.6562	Remote Similarity	NPD6456	Discontinued
0.656	Remote Similarity	NPD8110	Clinical (unspecified phase)
0.6556	Remote Similarity	NPD8289	Discontinued
0.6554	Remote Similarity	NPD6856	Discontinued
0.6552	Remote Similarity	NPD6545	Clinical (unspecified phase)
0.6544	Remote Similarity	NPD8046	Discontinued
0.6541	Remote Similarity	NPD5509	Phase 1
0.654	Remote Similarity	NPD3916	Clinical (unspecified phase)
0.654	Remote Similarity	NPD3917	Approved
0.654	Remote Similarity	NPD3918	Approved
0.6538	Remote Similarity	NPD8279	Clinical (unspecified phase)
0.6533	Remote Similarity	NPD5040	Clinical (unspecified phase)
0.6531	Remote Similarity	NPD7694	Discontinued
0.6525	Remote Similarity	NPD6243	Phase 3
0.6525	Remote Similarity	NPD6244	Phase 3
0.6522	Remote Similarity	NPD5575	Clinical (unspecified phase)
0.652	Remote Similarity	NPD3002	Clinical (unspecified phase)
0.6508	Remote Similarity	NPD459	Clinical (unspecified phase)
0.6507	Remote Similarity	NPD7767	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