NPASS Compound

Structure

NPC474594 OpenBabel07101718282D 22 25 0 0 1 0 0 0 0 0999 V2000 0.8660 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0029 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -3.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.4641 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -2.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.5981 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.4641 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -0.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -4.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.4152 -1.3090 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.4152 0.3090 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 5 1 0 0 0 0 1 6 1 0 0 0 0 2 4 2 0 0 0 0 2 7 1 0 0 0 0 3 21 1 0 0 0 0 3 22 1 0 0 0 0 4 5 1 0 0 0 0 4 8 1 0 0 0 0 5 9 2 0 0 0 0 6 10 1 0 0 0 0 6 16 1 6 0 0 0 7 13 2 0 0 0 0 7 21 1 0 0 0 0 8 11 2 0 0 0 0 8 14 1 0 0 0 0 9 12 1 0 0 0 0 9 15 1 0 0 0 0 10 12 1 0 0 0 0 10 17 1 1 0 0 0 11 13 1 0 0 0 0 11 18 1 0 0 0 0 12 19 1 1 0 0 0 13 22 1 0 0 0 0 14 15 2 0 0 0 0 14 20 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	307.07
Volume:	275.82
LogP:	-0.582
LogD:	-0.18
LogS:	-3.383
# Rotatable Bonds:	0
TPSA:	132.24
# H-Bond Aceptor:	8
# H-Bond Donor:	5
# Rings:	4
# Heavy Atoms:	8

MedChem Properties

QED Drug-Likeness Score:	0.433
Synthetic Accessibility Score:	4.154
Fsp3:	0.357
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.847
MDCK Permeability:	4.310074473323766e-06
Pgp-inhibitor:	0.001
Pgp-substrate:	0.412
Human Intestinal Absorption (HIA):	0.046
20% Bioavailability (F20%):	0.019
30% Bioavailability (F30%):	0.714

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.11
Plasma Protein Binding (PPB):	76.89813995361328%
Volume Distribution (VD):	1.13
Pgp-substrate:	12.896682739257812%

ADMET: Metabolism

CYP1A2-inhibitor:	0.173
CYP1A2-substrate:	0.502
CYP2C19-inhibitor:	0.021
CYP2C19-substrate:	0.096
CYP2C9-inhibitor:	0.004
CYP2C9-substrate:	0.233
CYP2D6-inhibitor:	0.026
CYP2D6-substrate:	0.16
CYP3A4-inhibitor:	0.048
CYP3A4-substrate:	0.027

ADMET: Excretion

Clearance (CL):	4.809
Half-life (T1/2):	0.605

ADMET: Toxicity

hERG Blockers:	0.018
Human Hepatotoxicity (H-HT):	0.137
Drug-inuced Liver Injury (DILI):	0.62
AMES Toxicity:	0.239
Rat Oral Acute Toxicity:	0.058
Maximum Recommended Daily Dose:	0.069
Skin Sensitization:	0.072
Carcinogencity:	0.12
Eye Corrosion:	0.003
Eye Irritation:	0.015
Respiratory Toxicity:	0.857

Download Data

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

Natural Product: NPC474594

Natural Product ID:	NPC474594
*Common Name:**	Isonarciclasine
IUPAC Name:	(2S,3R,4S)-2,3,4,7-tetrahydroxy-2,3,4,5-tetrahydro-1H-[1,3]dioxolo[4,5-j]phenanthridin-6-one
Synonyms:	Isonarciclasine
Standard InCHIKey:	JIMDZZQKKBUKLO-QDWQASTRSA-N
Standard InCHI:	InChI=1S/C14H13NO7/c16-6-1-5-4-2-7-13(22-3-21-7)11(18)8(4)14(20)15-9(5)12(19)10(6)17/h2,6,10,12,16-19H,1,3H2,(H,15,20)/t6-,10+,12-/m0/s1
SMILES:	C1C(C(C(C2=C1C3=CC4=C(C(=C3C(=O)N2)O)OCO4)O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL476486
PubChem CID:	5479394
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0001253] Quinolines and derivatives [CHEMONTID:0001908] Benzoquinolines [CHEMONTID:0000100] Phenanthridines and derivatives

*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
NPO33168	amaryllidaceae isoquinoline	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[1336040]

☑ 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
IC50	5
Others	5

Activity Type	# Activity
Organism	5
Others	5

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT33	Organism	Japanese encephalitis virus	Japanese encephalitis virus	IC50	=	0.72	ug.mL-1	PMID[456103]
NPT4327	Organism	Yellow fever virus	Yellow fever virus	IC50	=	0.22	ug.mL-1	PMID[456103]
NPT4328	Organism	Dengue virus type 4	Dengue virus 4	IC50	=	0.27	ug.mL-1	PMID[456103]
NPT27	Others	Unspecified		TI	=	2.1	n.a.	PMID[456103]
NPT27	Others	Unspecified		TI	=	4.1	n.a.	PMID[456103]
NPT27	Others	Unspecified		TI	=	18.5	n.a.	PMID[456103]
NPT341	Organism	Punta Toro virus	Punta Toro virus	IC50	=	0.28	ug.mL-1	PMID[456103]
NPT4329	Organism	Rift Valley fever virus	Rift Valley fever virus	IC50	=	3.3	ug.mL-1	PMID[456103]
NPT27	Others	Unspecified		TI	=	5.1	n.a.	PMID[456103]
NPT27	Others	Unspecified		TI	=	7.6	n.a.	PMID[456103]

☑ 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 NPC474594 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	573
0.1-0.2	2618
0.2-0.3	10959
0.3-0.4	7107
0.4-0.5	9680
0.5-0.6	9794
0.6-0.7	1755
0.7-0.8	197
0.8-0.85	11
0.85-0.9	1
0.9-0.95	0
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9579	High Similarity	NPC474595
0.915	High Similarity	NPC148409
0.8213	Intermediate Similarity	NPC203168
0.8173	Intermediate Similarity	NPC469390
0.8137	Intermediate Similarity	NPC164374
0.8137	Intermediate Similarity	NPC137929
0.8128	Intermediate Similarity	NPC66815
0.8116	Intermediate Similarity	NPC219664
0.8102	Intermediate Similarity	NPC476994
0.8102	Intermediate Similarity	NPC476997
0.8093	Intermediate Similarity	NPC200888
0.8065	Intermediate Similarity	NPC476996
0.8065	Intermediate Similarity	NPC476998
0.8019	Intermediate Similarity	NPC473822
0.797	Intermediate Similarity	NPC61350
0.7928	Intermediate Similarity	NPC476995
0.7923	Intermediate Similarity	NPC304183
0.7788	Intermediate Similarity	NPC118121
0.7788	Intermediate Similarity	NPC122463
0.7707	Intermediate Similarity	NPC224928
0.7704	Intermediate Similarity	NPC289743
0.7704	Intermediate Similarity	NPC110374
0.7696	Intermediate Similarity	NPC174049
0.7688	Intermediate Similarity	NPC62069
0.7656	Intermediate Similarity	NPC469440
0.7647	Intermediate Similarity	NPC79293
0.7647	Intermediate Similarity	NPC279401
0.7626	Intermediate Similarity	NPC1291
0.7626	Intermediate Similarity	NPC115343
0.7623	Intermediate Similarity	NPC201508
0.7612	Intermediate Similarity	NPC204385
0.7608	Intermediate Similarity	NPC199277
0.7608	Intermediate Similarity	NPC135887
0.7604	Intermediate Similarity	NPC204446
0.7598	Intermediate Similarity	NPC114335
0.7598	Intermediate Similarity	NPC141915
0.7598	Intermediate Similarity	NPC280964
0.7596	Intermediate Similarity	NPC234197
0.7593	Intermediate Similarity	NPC101312
0.7588	Intermediate Similarity	NPC206201
0.7556	Intermediate Similarity	NPC255800
0.7556	Intermediate Similarity	NPC96584
0.7554	Intermediate Similarity	NPC77878
0.7551	Intermediate Similarity	NPC182257
0.7545	Intermediate Similarity	NPC476999
0.7535	Intermediate Similarity	NPC202768
0.7535	Intermediate Similarity	NPC296482
0.7535	Intermediate Similarity	NPC202605
0.7535	Intermediate Similarity	NPC112206
0.7535	Intermediate Similarity	NPC96405
0.7535	Intermediate Similarity	NPC53069
0.7535	Intermediate Similarity	NPC171409
0.7512	Intermediate Similarity	NPC477019
0.7479	Intermediate Similarity	NPC183537
0.7475	Intermediate Similarity	NPC42591
0.7465	Intermediate Similarity	NPC235076
0.7402	Intermediate Similarity	NPC66083
0.7387	Intermediate Similarity	NPC194724
0.7383	Intermediate Similarity	NPC313189
0.7383	Intermediate Similarity	NPC135549
0.7373	Intermediate Similarity	NPC251160
0.7364	Intermediate Similarity	NPC100079
0.7364	Intermediate Similarity	NPC173080
0.7364	Intermediate Similarity	NPC23614
0.7339	Intermediate Similarity	NPC284141
0.733	Intermediate Similarity	NPC46451
0.7323	Intermediate Similarity	NPC304846
0.7317	Intermediate Similarity	NPC9867
0.731	Intermediate Similarity	NPC89199
0.731	Intermediate Similarity	NPC54125
0.7296	Intermediate Similarity	NPC160100
0.7284	Intermediate Similarity	NPC210296
0.7282	Intermediate Similarity	NPC214116
0.7281	Intermediate Similarity	NPC188420
0.7269	Intermediate Similarity	NPC469792
0.7265	Intermediate Similarity	NPC124313
0.726	Intermediate Similarity	NPC133140
0.726	Intermediate Similarity	NPC195268
0.7257	Intermediate Similarity	NPC302807
0.7253	Intermediate Similarity	NPC84164
0.7253	Intermediate Similarity	NPC207283
0.7249	Intermediate Similarity	NPC473182
0.7246	Intermediate Similarity	NPC173250
0.7238	Intermediate Similarity	NPC162653
0.723	Intermediate Similarity	NPC31930
0.7228	Intermediate Similarity	NPC187678
0.7222	Intermediate Similarity	NPC15406
0.7217	Intermediate Similarity	NPC277351
0.721	Intermediate Similarity	NPC217554
0.721	Intermediate Similarity	NPC49672
0.7209	Intermediate Similarity	NPC36229
0.7209	Intermediate Similarity	NPC476581
0.7209	Intermediate Similarity	NPC16452
0.7208	Intermediate Similarity	NPC120513
0.7203	Intermediate Similarity	NPC1608
0.719	Intermediate Similarity	NPC29472
0.7182	Intermediate Similarity	NPC271215
0.7182	Intermediate Similarity	NPC149471
0.7178	Intermediate Similarity	NPC2314
0.7171	Intermediate Similarity	NPC320394
0.7164	Intermediate Similarity	NPC312872
0.7162	Intermediate Similarity	NPC314552
0.7161	Intermediate Similarity	NPC58209
0.7156	Intermediate Similarity	NPC469589
0.7149	Intermediate Similarity	NPC129897
0.7149	Intermediate Similarity	NPC208364
0.7143	Intermediate Similarity	NPC134637
0.7143	Intermediate Similarity	NPC117717
0.7143	Intermediate Similarity	NPC469439
0.7143	Intermediate Similarity	NPC193777
0.7136	Intermediate Similarity	NPC316981
0.7136	Intermediate Similarity	NPC248642
0.713	Intermediate Similarity	NPC469594
0.7124	Intermediate Similarity	NPC11408
0.7122	Intermediate Similarity	NPC244554
0.7107	Intermediate Similarity	NPC69360
0.7101	Intermediate Similarity	NPC156576
0.7097	Intermediate Similarity	NPC471736
0.7094	Intermediate Similarity	NPC228040
0.7094	Intermediate Similarity	NPC168922
0.7094	Intermediate Similarity	NPC283152
0.7089	Intermediate Similarity	NPC107123
0.7082	Intermediate Similarity	NPC473183
0.7081	Intermediate Similarity	NPC186546
0.7081	Intermediate Similarity	NPC476576
0.7079	Intermediate Similarity	NPC311991
0.7078	Intermediate Similarity	NPC168250
0.7076	Intermediate Similarity	NPC188400
0.7075	Intermediate Similarity	NPC473053
0.7073	Intermediate Similarity	NPC15919
0.7056	Intermediate Similarity	NPC476578
0.7056	Intermediate Similarity	NPC476582
0.7056	Intermediate Similarity	NPC4071
0.7048	Intermediate Similarity	NPC82763
0.7044	Intermediate Similarity	NPC288943
0.7039	Intermediate Similarity	NPC108342
0.7039	Intermediate Similarity	NPC126284
0.7033	Intermediate Similarity	NPC22928
0.7033	Intermediate Similarity	NPC475919
0.7033	Intermediate Similarity	NPC474661
0.7033	Intermediate Similarity	NPC57036
0.7027	Intermediate Similarity	NPC471080
0.7027	Intermediate Similarity	NPC266931
0.7027	Intermediate Similarity	NPC469592
0.7018	Intermediate Similarity	NPC472111
0.7014	Intermediate Similarity	NPC294244
0.701	Intermediate Similarity	NPC474051
0.7009	Intermediate Similarity	NPC182907
0.7009	Intermediate Similarity	NPC189903
0.7005	Intermediate Similarity	NPC474607
0.7005	Intermediate Similarity	NPC159101
0.7004	Intermediate Similarity	NPC280272
0.7	Intermediate Similarity	NPC203373
0.7	Intermediate Similarity	NPC209769
0.7	Intermediate Similarity	NPC112676
0.6996	Remote Similarity	NPC34770
0.6996	Remote Similarity	NPC473184
0.699	Remote Similarity	NPC320223
0.699	Remote Similarity	NPC114364
0.6986	Remote Similarity	NPC219170
0.6986	Remote Similarity	NPC180253
0.6982	Remote Similarity	NPC48353
0.6979	Remote Similarity	NPC166722
0.6977	Remote Similarity	NPC128823
0.6976	Remote Similarity	NPC128560
0.6976	Remote Similarity	NPC199465
0.6976	Remote Similarity	NPC472168
0.6976	Remote Similarity	NPC229166
0.6974	Remote Similarity	NPC94842
0.6971	Remote Similarity	NPC474650
0.6971	Remote Similarity	NPC476575
0.6965	Remote Similarity	NPC24465
0.6964	Remote Similarity	NPC288349
0.6963	Remote Similarity	NPC243834
0.6963	Remote Similarity	NPC70956
0.6955	Remote Similarity	NPC470931
0.6952	Remote Similarity	NPC224293
0.6951	Remote Similarity	NPC162530
0.695	Remote Similarity	NPC24954
0.6949	Remote Similarity	NPC41501
0.6948	Remote Similarity	NPC131017
0.6947	Remote Similarity	NPC108826
0.6942	Remote Similarity	NPC478032
0.6941	Remote Similarity	NPC475768
0.6941	Remote Similarity	NPC476106
0.694	Remote Similarity	NPC217176
0.6935	Remote Similarity	NPC329837
0.6933	Remote Similarity	NPC473513
0.6931	Remote Similarity	NPC264850
0.6931	Remote Similarity	NPC13916
0.6927	Remote Similarity	NPC223427
0.6923	Remote Similarity	NPC209981
0.6923	Remote Similarity	NPC90875
0.6923	Remote Similarity	NPC153769
0.692	Remote Similarity	NPC99891
0.692	Remote Similarity	NPC119134
0.6919	Remote Similarity	NPC474904
0.6919	Remote Similarity	NPC296742
0.6916	Remote Similarity	NPC54066
0.6913	Remote Similarity	NPC202503

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 NPC474594 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	324
0.1-0.2	655
0.2-0.3	1153
0.3-0.4	2238
0.4-0.5	2748
0.5-0.6	1674
0.6-0.7	344
0.7-0.8	14
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
0.7576	Intermediate Similarity	NPD3920	Phase 2
0.7535	Intermediate Similarity	NPD3815	Phase 1
0.7535	Intermediate Similarity	NPD3816	Phase 1
0.7479	Intermediate Similarity	NPD6503	Clinical (unspecified phase)
0.7339	Intermediate Similarity	NPD7571	Clinical (unspecified phase)
0.733	Intermediate Similarity	NPD3763	Approved
0.7327	Intermediate Similarity	NPD4502	Phase 2
0.7322	Intermediate Similarity	NPD7169	Suspended
0.726	Intermediate Similarity	NPD3924	Approved
0.726	Intermediate Similarity	NPD3922	Approved
0.726	Intermediate Similarity	NPD3923	Approved
0.726	Intermediate Similarity	NPD3921	Approved
0.7249	Intermediate Similarity	NPD6494	Phase 2
0.7171	Intermediate Similarity	NPD5083	Clinical (unspecified phase)
0.7162	Intermediate Similarity	NPD5164	Discontinued
0.7149	Intermediate Similarity	NPD5902	Approved
0.7149	Intermediate Similarity	NPD5903	Approved
0.7114	Intermediate Similarity	NPD6773	Clinical (unspecified phase)
0.711	Intermediate Similarity	NPD5658	Approved
0.7064	Intermediate Similarity	NPD7222	Phase 2
0.7018	Intermediate Similarity	NPD4305	Clinical (unspecified phase)
0.7015	Intermediate Similarity	NPD4724	Clinical (unspecified phase)
0.6978	Remote Similarity	NPD8109	Clinical (unspecified phase)
0.6962	Remote Similarity	NPD1483	Discontinued
0.6953	Remote Similarity	NPD7558	Phase 2
0.6941	Remote Similarity	NPD3003	Approved
0.6909	Remote Similarity	NPD7452	Approved
0.6909	Remote Similarity	NPD6290	Phase 2
0.6909	Remote Similarity	NPD7453	Approved
0.6898	Remote Similarity	NPD2176	Approved
0.6898	Remote Similarity	NPD2175	Phase 3
0.6898	Remote Similarity	NPD2177	Approved
0.687	Remote Similarity	NPD7956	Approved
0.687	Remote Similarity	NPD7955	Approved
0.6857	Remote Similarity	NPD8244	Phase 2
0.6857	Remote Similarity	NPD5256	Discontinued
0.6842	Remote Similarity	NPD5930	Phase 3
0.6837	Remote Similarity	NPD5582	Discontinued
0.682	Remote Similarity	NPD1768	Approved
0.6818	Remote Similarity	NPD4034	Approved
0.6818	Remote Similarity	NPD4035	Approved
0.6818	Remote Similarity	NPD4037	Approved
0.6818	Remote Similarity	NPD4039	Approved
0.6818	Remote Similarity	NPD4036	Approved
0.6818	Remote Similarity	NPD32	Approved
0.6818	Remote Similarity	NPD31	Approved
0.6818	Remote Similarity	NPD4122	Approved
0.6818	Remote Similarity	NPD4038	Approved
0.6818	Remote Similarity	NPD4033	Approved
0.6814	Remote Similarity	NPD5612	Discontinued
0.681	Remote Similarity	NPD6553	Clinical (unspecified phase)
0.6807	Remote Similarity	NPD7025	Clinical (unspecified phase)
0.6798	Remote Similarity	NPD2899	Discontinued
0.6786	Remote Similarity	NPD5939	Approved
0.6786	Remote Similarity	NPD5936	Approved
0.6778	Remote Similarity	NPD7417	Discontinued
0.6769	Remote Similarity	NPD5070	Clinical (unspecified phase)
0.6759	Remote Similarity	NPD5512	Phase 3
0.6759	Remote Similarity	NPD6550	Discontinued
0.6756	Remote Similarity	NPD7069	Discontinued
0.6733	Remote Similarity	NPD7803	Approved
0.6728	Remote Similarity	NPD1229	Phase 2
0.6725	Remote Similarity	NPD7194	Discontinued
0.6723	Remote Similarity	NPD5805	Approved
0.6721	Remote Similarity	NPD6525	Clinical (unspecified phase)
0.6713	Remote Similarity	NPD6590	Discontinued
0.6712	Remote Similarity	NPD5530	Phase 1
0.6697	Remote Similarity	NPD6669	Phase 2
0.6682	Remote Similarity	NPD5429	Discontinued
0.6682	Remote Similarity	NPD2845	Phase 2
0.6682	Remote Similarity	NPD2843	Phase 2
0.6681	Remote Similarity	NPD6985	Discontinued
0.668	Remote Similarity	NPD6517	Phase 3
0.668	Remote Similarity	NPD7862	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6257	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD3386	Phase 2
0.6667	Remote Similarity	NPD3837	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6361	Phase 2
0.6652	Remote Similarity	NPD3875	Discontinued
0.664	Remote Similarity	NPD7708	Approved
0.6638	Remote Similarity	NPD1954	Phase 1
0.6637	Remote Similarity	NPD3842	Clinical (unspecified phase)
0.6636	Remote Similarity	NPD6861	Clinical (unspecified phase)
0.6636	Remote Similarity	NPD4418	Discontinued
0.6633	Remote Similarity	NPD4005	Discontinued
0.6624	Remote Similarity	NPD4885	Approved
0.662	Remote Similarity	NPD6569	Phase 2
0.6607	Remote Similarity	NPD1392	Approved
0.6607	Remote Similarity	NPD7263	Phase 2
0.6589	Remote Similarity	NPD4663	Approved
0.6588	Remote Similarity	NPD4204	Approved
0.6588	Remote Similarity	NPD4203	Approved
0.6573	Remote Similarity	NPD4926	Clinical (unspecified phase)
0.6573	Remote Similarity	NPD8054	Approved
0.6573	Remote Similarity	NPD8053	Approved
0.6569	Remote Similarity	NPD7975	Clinical (unspecified phase)
0.6567	Remote Similarity	NPD6736	Discontinued
0.656	Remote Similarity	NPD6491	Clinical (unspecified phase)
0.6558	Remote Similarity	NPD7906	Approved
0.6553	Remote Similarity	NPD7676	Clinical (unspecified phase)
0.6553	Remote Similarity	NPD7675	Phase 3
0.6553	Remote Similarity	NPD7674	Phase 3
0.6545	Remote Similarity	NPD2727	Phase 2
0.6543	Remote Similarity	NPD4876	Phase 3
0.6543	Remote Similarity	NPD4875	Phase 3
0.6537	Remote Similarity	NPD7395	Discontinued
0.6535	Remote Similarity	NPD4927	Discontinued
0.6535	Remote Similarity	NPD7827	Phase 1
0.6532	Remote Similarity	NPD7859	Phase 2
0.6527	Remote Similarity	NPD4080	Discontinued
0.6527	Remote Similarity	NPD6625	Approved
0.6526	Remote Similarity	NPD4577	Approved
0.6526	Remote Similarity	NPD4578	Approved
0.6523	Remote Similarity	NPD8364	Approved
0.6523	Remote Similarity	NPD8363	Approved
0.6509	Remote Similarity	NPD7414	Clinical (unspecified phase)
0.6502	Remote Similarity	NPD5006	Approved
0.6502	Remote Similarity	NPD2977	Approved
0.6502	Remote Similarity	NPD2978	Approved
0.6502	Remote Similarity	NPD5005	Approved
0.6502	Remote Similarity	NPD6477	Clinical (unspecified phase)
0.65	Remote Similarity	NPD4605	Approved
0.65	Remote Similarity	NPD6964	Approved
0.65	Remote Similarity	NPD6963	Approved
0.65	Remote Similarity	NPD6988	Phase 1
0.65	Remote Similarity	NPD4604	Approved
0.6495	Remote Similarity	NPD6344	Clinical (unspecified phase)
0.6493	Remote Similarity	NPD1620	Clinical (unspecified phase)
0.6493	Remote Similarity	NPD1503	Clinical (unspecified phase)
0.6491	Remote Similarity	NPD4131	Phase 3
0.6483	Remote Similarity	NPD3263	Phase 3
0.6473	Remote Similarity	NPD8365	Clinical (unspecified phase)
0.6471	Remote Similarity	NPD6877	Discontinued
0.6459	Remote Similarity	NPD677	Clinical (unspecified phase)
0.6453	Remote Similarity	NPD5507	Approved
0.6453	Remote Similarity	NPD5506	Approved
0.6448	Remote Similarity	NPD7684	Approved
0.6448	Remote Similarity	NPD7682	Approved
0.6445	Remote Similarity	NPD6642	Approved
0.6445	Remote Similarity	NPD6159	Phase 2
0.6445	Remote Similarity	NPD6641	Approved
0.6444	Remote Similarity	NPD1505	Phase 2
0.6441	Remote Similarity	NPD4052	Clinical (unspecified phase)
0.6441	Remote Similarity	NPD4118	Clinical (unspecified phase)
0.6441	Remote Similarity	NPD3925	Approved
0.6438	Remote Similarity	NPD4551	Phase 2
0.6438	Remote Similarity	NPD7125	Discontinued
0.6435	Remote Similarity	NPD2383	Phase 1
0.6429	Remote Similarity	NPD7710	Clinical (unspecified phase)
0.6429	Remote Similarity	NPD8461	Discontinued
0.6426	Remote Similarity	NPD1856	Discontinued
0.6423	Remote Similarity	NPD6230	Discontinued
0.6422	Remote Similarity	NPD6656	Clinical (unspecified phase)
0.6419	Remote Similarity	NPD6220	Phase 3
0.6414	Remote Similarity	NPD8442	Discontinued
0.6414	Remote Similarity	NPD7426	Phase 1
0.6411	Remote Similarity	NPD4083	Discontinued
0.6408	Remote Similarity	NPD4055	Discovery
0.6408	Remote Similarity	NPD6716	Phase 1
0.6407	Remote Similarity	NPD5417	Clinical (unspecified phase)
0.6404	Remote Similarity	NPD4437	Phase 3
0.639	Remote Similarity	NPD6723	Discontinued
0.6389	Remote Similarity	NPD4375	Approved
0.6388	Remote Similarity	NPD6814	Phase 3
0.6385	Remote Similarity	NPD7007	Discovery
0.6384	Remote Similarity	NPD7134	Clinical (unspecified phase)
0.6381	Remote Similarity	NPD7418	Discontinued
0.6375	Remote Similarity	NPD6962	Phase 2
0.6373	Remote Similarity	NPD9382	Approved
0.6373	Remote Similarity	NPD9383	Approved
0.6372	Remote Similarity	NPD3946	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD5945	Phase 1
0.6364	Remote Similarity	NPD1038	Approved
0.6364	Remote Similarity	NPD7474	Suspended
0.6364	Remote Similarity	NPD5944	Phase 1
0.636	Remote Similarity	NPD5863	Clinical (unspecified phase)
0.6355	Remote Similarity	NPD3296	Phase 1
0.6351	Remote Similarity	NPD5602	Clinical (unspecified phase)
0.6348	Remote Similarity	NPD5067	Phase 2
0.6348	Remote Similarity	NPD5066	Phase 2
0.6341	Remote Similarity	NPD5833	Phase 1
0.6339	Remote Similarity	NPD6219	Discontinued
0.6339	Remote Similarity	NPD4396	Clinical (unspecified phase)
0.6336	Remote Similarity	NPD4897	Phase 2
0.6333	Remote Similarity	NPD7567	Approved
0.6333	Remote Similarity	NPD7589	Clinical (unspecified phase)
0.6331	Remote Similarity	NPD5488	Discontinued
0.6329	Remote Similarity	NPD5604	Discontinued
0.6327	Remote Similarity	NPD5905	Phase 1
0.6323	Remote Similarity	NPD7889	Clinical (unspecified phase)
0.6323	Remote Similarity	NPD4420	Approved
0.632	Remote Similarity	NPD6243	Phase 3
0.632	Remote Similarity	NPD6244	Phase 3
0.6314	Remote Similarity	NPD6298	Discontinued
0.6312	Remote Similarity	NPD8465	Approved
0.6312	Remote Similarity	NPD8467	Approved
0.6312	Remote Similarity	NPD8466	Approved
0.6303	Remote Similarity	NPD2489	Approved
0.6303	Remote Similarity	NPD7719	Discontinued
0.6303	Remote Similarity	NPD6246	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