NPASS Compound

Structure

NPC470879 OpenBabel07101719512D 24 28 0 0 1 0 0 0 0 0999 V2000 -1.3523 4.0404 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3755 1.5062 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5491 -1.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4152 -1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7407 2.0456 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3776 0.9425 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8171 -1.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4093 2.1454 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5878 -0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6831 -1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6831 1.2769 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1038 2.4799 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5491 0.1910 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -1.3517 1.3767 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9511 -1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6831 -0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9886 0.9425 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8171 0.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9511 -0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4152 -0.3090 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -2.1785 3.4771 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.4507 0.9428 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -1.6180 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 21 1 0 0 0 0 2 22 1 0 0 0 0 3 4 1 0 0 0 0 3 10 1 0 0 0 0 4 20 1 0 0 0 0 5 11 2 0 0 0 0 5 12 1 0 0 0 0 6 11 1 0 0 0 0 6 13 1 0 0 0 0 7 10 2 0 0 0 0 7 15 1 0 0 0 0 8 12 2 0 0 0 0 8 14 1 0 0 0 0 9 23 1 0 0 0 0 9 24 1 0 0 0 0 10 16 1 0 0 0 0 11 17 1 0 0 0 0 12 21 1 0 0 0 0 13 16 1 0 0 0 0 13 20 1 0 0 0 0 14 17 2 0 0 0 0 14 22 1 0 0 0 0 15 19 2 0 0 0 0 15 23 1 0 0 0 0 16 18 2 0 0 0 0 17 18 1 0 0 0 0 18 19 1 0 0 0 0 19 24 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	325.13
Volume:	324.737
LogP:	2.88
LogD:	2.812
LogS:	-3.029
# Rotatable Bonds:	2
TPSA:	48.95
# H-Bond Aceptor:	5
# H-Bond Donor:	1
# Rings:	5
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.92
Synthetic Accessibility Score:	3.255
Fsp3:	0.368
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.074
MDCK Permeability:	1.5896048353170045e-05
Pgp-inhibitor:	0.067
Pgp-substrate:	0.543
Human Intestinal Absorption (HIA):	0.002
20% Bioavailability (F20%):	0.002
30% Bioavailability (F30%):	0.002

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.867
Plasma Protein Binding (PPB):	83.85870361328125%
Volume Distribution (VD):	2.716
Pgp-substrate:	5.228916168212891%

ADMET: Metabolism

CYP1A2-inhibitor:	0.721
CYP1A2-substrate:	0.809
CYP2C19-inhibitor:	0.388
CYP2C19-substrate:	0.86
CYP2C9-inhibitor:	0.009
CYP2C9-substrate:	0.785
CYP2D6-inhibitor:	0.787
CYP2D6-substrate:	0.939
CYP3A4-inhibitor:	0.515
CYP3A4-substrate:	0.86

ADMET: Excretion

Clearance (CL):	8.111
Half-life (T1/2):	0.159

ADMET: Toxicity

hERG Blockers:	0.798
Human Hepatotoxicity (H-HT):	0.323
Drug-inuced Liver Injury (DILI):	0.535
AMES Toxicity:	0.563
Rat Oral Acute Toxicity:	0.695
Maximum Recommended Daily Dose:	0.936
Skin Sensitization:	0.159
Carcinogencity:	0.101
Eye Corrosion:	0.003
Eye Irritation:	0.009
Respiratory Toxicity:	0.917

Download Data

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

Natural Product: NPC470879

Natural Product ID:	NPC470879
*Common Name:**	RYQZFXDNXUJJOP-UHFFFAOYSA-N
IUPAC Name:	n.a.
Synonyms:	(+/-)-Discoguattine
Standard InCHIKey:	RYQZFXDNXUJJOP-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C19H19NO4/c1-21-12-5-11-6-13-16-10(3-4-20-13)7-15-19(24-9-23-15)18(16)17(11)14(8-12)22-2/h5,7-8,13,20H,3-4,6,9H2,1-2H3
SMILES:	COC1=CC2=C(C(=C1)OC)C3=C4C(C2)NCCC4=CC5=C3OCO5
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL227479
PubChem CID:	14604490
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000279] Alkaloids and derivatives [CHEMONTID:0000381] Aporphines

*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
NPO18509	Fissistigma oldhamii	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10978218]
NPO18509	Fissistigma oldhamii	Species	Annonaceae	Eukaryota	stem	n.a.	n.a.	PMID[17081761]
NPO18509	Fissistigma oldhamii	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

☑ 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	2
Others	3

Activity Type	# Activity
Cell Line	1
Others	4

Target ID	Target Type	Target Name	Activity Type	Activity Relation	Value	Unit	Reference
NPT1076	Cell Line	B-cells	IC50	=	1690.0	nM	PMID[572114]
NPT27	Others	Unspecified	CC50	=	15600.0	nM	PMID[572114]
NPT2	Others	Unspecified	IC50	=	2430.0	nM	PMID[572114]
NPT2	Others	Unspecified	Ratio CC50/IC50	=	6.0	n.a.	PMID[572114]
NPT2	Others	Unspecified	Ratio CC50/IC50	=	9.0	n.a.	PMID[572114]

☑ 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 NPC470879 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	402
0.1-0.2	2149
0.2-0.3	9476
0.3-0.4	8735
0.4-0.5	6974
0.5-0.6	11100
0.6-0.7	3007
0.7-0.8	607
0.8-0.85	168
0.85-0.9	47
0.9-0.95	22
0.95-1	10

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC258695
0.9939	High Similarity	NPC474506
0.9939	High Similarity	NPC32413
0.9816	High Similarity	NPC23219
0.9755	High Similarity	NPC112575
0.9701	High Similarity	NPC57036
0.963	High Similarity	NPC6152
0.9571	High Similarity	NPC149090
0.9571	High Similarity	NPC19520
0.9527	High Similarity	NPC186546
0.9527	High Similarity	NPC476576
0.9506	High Similarity	NPC204947
0.9325	High Similarity	NPC86144
0.9325	High Similarity	NPC304659
0.9268	High Similarity	NPC247389
0.9264	High Similarity	NPC302527
0.9264	High Similarity	NPC16805
0.9264	High Similarity	NPC167546
0.9249	High Similarity	NPC117717
0.9235	High Similarity	NPC135772
0.9231	High Similarity	NPC476574
0.9231	High Similarity	NPC477561
0.9231	High Similarity	NPC155442
0.9231	High Similarity	NPC312918
0.9207	High Similarity	NPC219341
0.9207	High Similarity	NPC476432
0.9207	High Similarity	NPC24264
0.9202	High Similarity	NPC189470
0.9172	High Similarity	NPC267408
0.9152	High Similarity	NPC210918
0.9146	High Similarity	NPC225774
0.9107	High Similarity	NPC477558
0.9059	High Similarity	NPC474507
0.8963	High Similarity	NPC306902
0.8963	High Similarity	NPC160298
0.8963	High Similarity	NPC232924
0.8963	High Similarity	NPC477559
0.8963	High Similarity	NPC266753
0.8941	High Similarity	NPC173416
0.8941	High Similarity	NPC148709
0.8941	High Similarity	NPC476577
0.8929	High Similarity	NPC152212
0.8914	High Similarity	NPC82763
0.8908	High Similarity	NPC214116
0.8896	High Similarity	NPC126519
0.8896	High Similarity	NPC203784
0.8896	High Similarity	NPC170503
0.8889	High Similarity	NPC114364
0.8889	High Similarity	NPC320223
0.8882	High Similarity	NPC229166
0.8882	High Similarity	NPC128560
0.8882	High Similarity	NPC199465
0.8864	High Similarity	NPC475754
0.8844	High Similarity	NPC476575
0.8841	High Similarity	NPC476572
0.8834	High Similarity	NPC325871
0.8834	High Similarity	NPC99659
0.8824	High Similarity	NPC192135
0.8824	High Similarity	NPC66341
0.8824	High Similarity	NPC477020
0.8817	High Similarity	NPC26240
0.8817	High Similarity	NPC477562
0.8817	High Similarity	NPC69712
0.8765	High Similarity	NPC239775
0.8736	High Similarity	NPC248642
0.8736	High Similarity	NPC275132
0.8701	High Similarity	NPC281581
0.8698	High Similarity	NPC298979
0.8686	High Similarity	NPC156576
0.8675	High Similarity	NPC7393
0.8656	High Similarity	NPC46990
0.8647	High Similarity	NPC241055
0.8629	High Similarity	NPC116284
0.8621	High Similarity	NPC126284
0.8596	High Similarity	NPC168753
0.8596	High Similarity	NPC118274
0.858	High Similarity	NPC168409
0.8537	High Similarity	NPC81733
0.8537	High Similarity	NPC326316
0.8529	High Similarity	NPC81247
0.8529	High Similarity	NPC35627
0.8529	High Similarity	NPC476573
0.8485	Intermediate Similarity	NPC114124
0.848	Intermediate Similarity	NPC145832
0.848	Intermediate Similarity	NPC306555
0.848	Intermediate Similarity	NPC474931
0.848	Intermediate Similarity	NPC117188
0.848	Intermediate Similarity	NPC81218
0.848	Intermediate Similarity	NPC205421
0.848	Intermediate Similarity	NPC158376
0.848	Intermediate Similarity	NPC12053
0.8471	Intermediate Similarity	NPC253043
0.8471	Intermediate Similarity	NPC212794
0.8471	Intermediate Similarity	NPC196447
0.8471	Intermediate Similarity	NPC78222
0.8471	Intermediate Similarity	NPC96603
0.8471	Intermediate Similarity	NPC477563
0.8471	Intermediate Similarity	NPC13504
0.8471	Intermediate Similarity	NPC306843
0.8471	Intermediate Similarity	NPC136508
0.8457	Intermediate Similarity	NPC148693
0.8457	Intermediate Similarity	NPC294790
0.8457	Intermediate Similarity	NPC118633
0.8436	Intermediate Similarity	NPC237579
0.8421	Intermediate Similarity	NPC56887
0.8421	Intermediate Similarity	NPC193853
0.8421	Intermediate Similarity	NPC223077
0.8418	Intermediate Similarity	NPC299990
0.8418	Intermediate Similarity	NPC73492
0.8412	Intermediate Similarity	NPC324144
0.8383	Intermediate Similarity	NPC244112
0.8383	Intermediate Similarity	NPC41178
0.8383	Intermediate Similarity	NPC216459
0.8383	Intermediate Similarity	NPC138487
0.8382	Intermediate Similarity	NPC75958
0.838	Intermediate Similarity	NPC47077
0.838	Intermediate Similarity	NPC14507
0.8371	Intermediate Similarity	NPC302275
0.8363	Intermediate Similarity	NPC180306
0.8363	Intermediate Similarity	NPC209377
0.8354	Intermediate Similarity	NPC475959
0.8354	Intermediate Similarity	NPC59907
0.8354	Intermediate Similarity	NPC37144
0.8333	Intermediate Similarity	NPC146288
0.8333	Intermediate Similarity	NPC312531
0.8305	Intermediate Similarity	NPC243454
0.8305	Intermediate Similarity	NPC475479
0.8304	Intermediate Similarity	NPC1229
0.8274	Intermediate Similarity	NPC123323
0.8263	Intermediate Similarity	NPC210148
0.8263	Intermediate Similarity	NPC233029
0.8258	Intermediate Similarity	NPC239584
0.8251	Intermediate Similarity	NPC256124
0.8245	Intermediate Similarity	NPC244606
0.8245	Intermediate Similarity	NPC156728
0.8235	Intermediate Similarity	NPC477080
0.8225	Intermediate Similarity	NPC234392
0.8225	Intermediate Similarity	NPC31311
0.8208	Intermediate Similarity	NPC68328
0.8208	Intermediate Similarity	NPC195392
0.8193	Intermediate Similarity	NPC211296
0.8187	Intermediate Similarity	NPC166014
0.8187	Intermediate Similarity	NPC27410
0.8182	Intermediate Similarity	NPC2314
0.8172	Intermediate Similarity	NPC212163
0.8166	Intermediate Similarity	NPC76079
0.8156	Intermediate Similarity	NPC179704
0.815	Intermediate Similarity	NPC24465
0.8142	Intermediate Similarity	NPC475597
0.8142	Intermediate Similarity	NPC473716
0.814	Intermediate Similarity	NPC79402
0.814	Intermediate Similarity	NPC80759
0.8136	Intermediate Similarity	NPC329969
0.8133	Intermediate Similarity	NPC130941
0.8125	Intermediate Similarity	NPC65403
0.8122	Intermediate Similarity	NPC9867
0.8103	Intermediate Similarity	NPC264850
0.8103	Intermediate Similarity	NPC13916
0.8101	Intermediate Similarity	NPC220961
0.8101	Intermediate Similarity	NPC244554
0.8098	Intermediate Similarity	NPC302001
0.8098	Intermediate Similarity	NPC24260
0.8098	Intermediate Similarity	NPC478093
0.809	Intermediate Similarity	NPC287588
0.8085	Intermediate Similarity	NPC295676
0.8084	Intermediate Similarity	NPC219162
0.8081	Intermediate Similarity	NPC230956
0.8081	Intermediate Similarity	NPC271388
0.8081	Intermediate Similarity	NPC205255
0.8081	Intermediate Similarity	NPC235143
0.8081	Intermediate Similarity	NPC119649
0.807	Intermediate Similarity	NPC79328
0.8059	Intermediate Similarity	NPC93593
0.8056	Intermediate Similarity	NPC257269
0.8054	Intermediate Similarity	NPC478092
0.8054	Intermediate Similarity	NPC478091
0.8054	Intermediate Similarity	NPC30182
0.8054	Intermediate Similarity	NPC473589
0.8046	Intermediate Similarity	NPC232514
0.8046	Intermediate Similarity	NPC276944
0.8046	Intermediate Similarity	NPC238530
0.8034	Intermediate Similarity	NPC187678
0.8023	Intermediate Similarity	NPC227060
0.8023	Intermediate Similarity	NPC221864
0.8023	Intermediate Similarity	NPC10908
0.8023	Intermediate Similarity	NPC63646
0.8023	Intermediate Similarity	NPC231371
0.8023	Intermediate Similarity	NPC317439
0.8023	Intermediate Similarity	NPC76682
0.8023	Intermediate Similarity	NPC317145
0.8023	Intermediate Similarity	NPC111485
0.8023	Intermediate Similarity	NPC115284
0.8023	Intermediate Similarity	NPC198498
0.8023	Intermediate Similarity	NPC276890
0.8022	Intermediate Similarity	NPC95426
0.8022	Intermediate Similarity	NPC16357
0.8022	Intermediate Similarity	NPC302245
0.8012	Intermediate Similarity	NPC29647
0.8011	Intermediate Similarity	NPC249405
0.8	Intermediate Similarity	NPC119068

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 NPC470879 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	211
0.1-0.2	829
0.2-0.3	1135
0.3-0.4	2414
0.4-0.5	2628
0.5-0.6	1380
0.6-0.7	464
0.7-0.8	85
0.8-0.85	4
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8023	Intermediate Similarity	NPD8099	Discontinued
0.8023	Intermediate Similarity	NPD8252	Approved
0.8023	Intermediate Similarity	NPD8251	Approved
0.8	Intermediate Similarity	NPD8453	Clinical (unspecified phase)
0.7978	Intermediate Similarity	NPD8156	Discontinued
0.7964	Intermediate Similarity	NPD4584	Approved
0.7953	Intermediate Similarity	NPD7298	Approved
0.7927	Intermediate Similarity	NPD4664	Clinical (unspecified phase)
0.7919	Intermediate Similarity	NPD6788	Approved
0.7857	Intermediate Similarity	NPD1424	Approved
0.7809	Intermediate Similarity	NPD4481	Phase 3
0.7797	Intermediate Similarity	NPD3051	Approved
0.7765	Intermediate Similarity	NPD6031	Approved
0.7765	Intermediate Similarity	NPD6030	Approved
0.7765	Intermediate Similarity	NPD4727	Phase 1
0.7717	Intermediate Similarity	NPD8054	Approved
0.7717	Intermediate Similarity	NPD8053	Approved
0.7688	Intermediate Similarity	NPD7906	Approved
0.7679	Intermediate Similarity	NPD5084	Clinical (unspecified phase)
0.7677	Intermediate Similarity	NPD7827	Phase 1
0.7668	Intermediate Similarity	NPD5005	Approved
0.7668	Intermediate Similarity	NPD5006	Approved
0.7654	Intermediate Similarity	NPD2970	Approved
0.7654	Intermediate Similarity	NPD2969	Approved
0.7644	Intermediate Similarity	NPD3383	Approved
0.7644	Intermediate Similarity	NPD3384	Approved
0.7644	Intermediate Similarity	NPD3382	Approved
0.76	Intermediate Similarity	NPD4585	Approved
0.76	Intermediate Similarity	NPD2977	Approved
0.76	Intermediate Similarity	NPD2978	Approved
0.7568	Intermediate Similarity	NPD4578	Approved
0.7568	Intermediate Similarity	NPD4577	Approved
0.7552	Intermediate Similarity	NPD4420	Approved
0.7546	Intermediate Similarity	NPD554	Clinical (unspecified phase)
0.754	Intermediate Similarity	NPD4663	Approved
0.7514	Intermediate Similarity	NPD27	Approved
0.7514	Intermediate Similarity	NPD2489	Approved
0.7514	Intermediate Similarity	NPD4581	Clinical (unspecified phase)
0.7487	Intermediate Similarity	NPD5087	Clinical (unspecified phase)
0.7485	Intermediate Similarity	NPD2421	Approved
0.7485	Intermediate Similarity	NPD2420	Approved
0.7473	Intermediate Similarity	NPD7313	Approved
0.7473	Intermediate Similarity	NPD7311	Approved
0.7473	Intermediate Similarity	NPD7310	Approved
0.7473	Intermediate Similarity	NPD7312	Approved
0.7472	Intermediate Similarity	NPD4055	Discovery
0.7471	Intermediate Similarity	NPD5307	Clinical (unspecified phase)
0.7471	Intermediate Similarity	NPD7261	Clinical (unspecified phase)
0.7457	Intermediate Similarity	NPD5976	Discontinued
0.7433	Intermediate Similarity	NPD7309	Approved
0.7427	Intermediate Similarity	NPD6783	Clinical (unspecified phase)
0.7427	Intermediate Similarity	NPD2422	Clinical (unspecified phase)
0.7427	Intermediate Similarity	NPD3845	Phase 1
0.7423	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.7399	Intermediate Similarity	NPD3647	Clinical (unspecified phase)
0.738	Intermediate Similarity	NPD2968	Approved
0.738	Intermediate Similarity	NPD2971	Approved
0.7371	Intermediate Similarity	NPD4017	Approved
0.7348	Intermediate Similarity	NPD6107	Approved
0.732	Intermediate Similarity	NPD2975	Approved
0.732	Intermediate Similarity	NPD2974	Approved
0.732	Intermediate Similarity	NPD2973	Approved
0.7308	Intermediate Similarity	NPD4166	Phase 2
0.7303	Intermediate Similarity	NPD6818	Clinical (unspecified phase)
0.73	Intermediate Similarity	NPD4859	Phase 1
0.7293	Intermediate Similarity	NPD7201	Clinical (unspecified phase)
0.7277	Intermediate Similarity	NPD6723	Discontinued
0.7257	Intermediate Similarity	NPD3640	Phase 3
0.7257	Intermediate Similarity	NPD3639	Approved
0.7257	Intermediate Similarity	NPD3641	Approved
0.7249	Intermediate Similarity	NPD7090	Clinical (unspecified phase)
0.7245	Intermediate Similarity	NPD8095	Phase 1
0.7225	Intermediate Similarity	NPD7124	Phase 2
0.7219	Intermediate Similarity	NPD6297	Approved
0.7213	Intermediate Similarity	NPD6071	Discontinued
0.7208	Intermediate Similarity	NPD4580	Approved
0.7198	Intermediate Similarity	NPD5677	Discontinued
0.7186	Intermediate Similarity	NPD3109	Approved
0.7186	Intermediate Similarity	NPD3110	Approved
0.7184	Intermediate Similarity	NPD7598	Phase 2
0.7175	Intermediate Similarity	NPD4005	Discontinued
0.7172	Intermediate Similarity	NPD2494	Approved
0.7172	Intermediate Similarity	NPD3452	Approved
0.7172	Intermediate Similarity	NPD2493	Approved
0.7172	Intermediate Similarity	NPD3450	Approved
0.7168	Intermediate Similarity	NPD5241	Discontinued
0.7167	Intermediate Similarity	NPD2560	Approved
0.7167	Intermediate Similarity	NPD2563	Approved
0.7135	Intermediate Similarity	NPD2898	Approved
0.7128	Intermediate Similarity	NPD6996	Clinical (unspecified phase)
0.7118	Intermediate Similarity	NPD6028	Clinical (unspecified phase)
0.7118	Intermediate Similarity	NPD6029	Clinical (unspecified phase)
0.711	Intermediate Similarity	NPD3977	Clinical (unspecified phase)
0.7108	Intermediate Similarity	NPD2669	Clinical (unspecified phase)
0.7095	Intermediate Similarity	NPD4773	Phase 2
0.7095	Intermediate Similarity	NPD4772	Phase 2
0.7088	Intermediate Similarity	NPD7832	Clinical (unspecified phase)
0.7088	Intermediate Similarity	NPD7833	Phase 2
0.7088	Intermediate Similarity	NPD7831	Phase 2
0.7088	Intermediate Similarity	NPD7975	Clinical (unspecified phase)
0.7085	Intermediate Similarity	NPD8152	Approved
0.7085	Intermediate Similarity	NPD8153	Approved
0.7068	Intermediate Similarity	NPD6853	Approved
0.7068	Intermediate Similarity	NPD6851	Approved
0.7065	Intermediate Similarity	NPD4583	Approved
0.7065	Intermediate Similarity	NPD4582	Approved
0.7062	Intermediate Similarity	NPD2488	Approved
0.7062	Intermediate Similarity	NPD2490	Approved
0.7052	Intermediate Similarity	NPD3060	Approved
0.7037	Intermediate Similarity	NPD6625	Approved
0.7027	Intermediate Similarity	NPD4010	Discontinued
0.7021	Intermediate Similarity	NPD42	Phase 2
0.7021	Intermediate Similarity	NPD6042	Phase 2
0.7015	Intermediate Similarity	NPD4004	Approved
0.7015	Intermediate Similarity	NPD4002	Approved
0.7011	Intermediate Similarity	NPD5754	Discontinued
0.7005	Intermediate Similarity	NPD7667	Clinical (unspecified phase)
0.6995	Remote Similarity	NPD5604	Discontinued
0.6977	Remote Similarity	NPD1632	Clinical (unspecified phase)
0.6973	Remote Similarity	NPD7802	Discontinued
0.6971	Remote Similarity	NPD5160	Discontinued
0.6965	Remote Similarity	NPD3516	Approved
0.6965	Remote Similarity	NPD3515	Approved
0.6964	Remote Similarity	NPD5718	Phase 2
0.6961	Remote Similarity	NPD37	Approved
0.6959	Remote Similarity	NPD3349	Phase 2
0.6957	Remote Similarity	NPD5709	Phase 3
0.695	Remote Similarity	NPD5457	Discontinued
0.6923	Remote Similarity	NPD7235	Clinical (unspecified phase)
0.6919	Remote Similarity	NPD4666	Phase 3
0.6906	Remote Similarity	NPD5089	Approved
0.6906	Remote Similarity	NPD5090	Approved
0.6897	Remote Similarity	NPD7045	Clinical (unspecified phase)
0.689	Remote Similarity	NPD7047	Phase 3
0.6875	Remote Similarity	NPD7549	Discontinued
0.6872	Remote Similarity	NPD3763	Approved
0.6866	Remote Similarity	NPD6612	Phase 2
0.6866	Remote Similarity	NPD4107	Approved
0.6865	Remote Similarity	NPD7400	Phase 3
0.686	Remote Similarity	NPD6111	Discontinued
0.6857	Remote Similarity	NPD4162	Approved
0.6857	Remote Similarity	NPD5177	Phase 3
0.6854	Remote Similarity	NPD6997	Phase 2
0.6848	Remote Similarity	NPD4967	Phase 2
0.6848	Remote Similarity	NPD4966	Approved
0.6848	Remote Similarity	NPD4965	Approved
0.6839	Remote Similarity	NPD7280	Phase 3
0.6839	Remote Similarity	NPD3534	Clinical (unspecified phase)
0.6839	Remote Similarity	NPD5917	Clinical (unspecified phase)
0.6839	Remote Similarity	NPD7281	Phase 3
0.6837	Remote Similarity	NPD3408	Clinical (unspecified phase)
0.6829	Remote Similarity	NPD3705	Approved
0.6828	Remote Similarity	NPD6037	Discontinued
0.6825	Remote Similarity	NPD5602	Clinical (unspecified phase)
0.6824	Remote Similarity	NPD4474	Approved
0.6824	Remote Similarity	NPD4475	Approved
0.6821	Remote Similarity	NPD4108	Discontinued
0.6818	Remote Similarity	NPD7466	Approved
0.6816	Remote Similarity	NPD5261	Clinical (unspecified phase)
0.6814	Remote Similarity	NPD4040	Phase 1
0.6809	Remote Similarity	NPD5242	Approved
0.6804	Remote Similarity	NPD6618	Phase 2
0.6798	Remote Similarity	NPD3124	Discontinued
0.6792	Remote Similarity	NPD8318	Clinical (unspecified phase)
0.6789	Remote Similarity	NPD5708	Clinical (unspecified phase)
0.6786	Remote Similarity	NPD6841	Approved
0.6786	Remote Similarity	NPD6843	Phase 3
0.6786	Remote Similarity	NPD6842	Approved
0.6786	Remote Similarity	NPD7243	Clinical (unspecified phase)
0.6782	Remote Similarity	NPD3454	Phase 3
0.678	Remote Similarity	NPD2677	Approved
0.6776	Remote Similarity	NPD5720	Discontinued
0.6774	Remote Similarity	NPD6234	Discontinued
0.6763	Remote Similarity	NPD6896	Approved
0.6763	Remote Similarity	NPD6895	Approved
0.6763	Remote Similarity	NPD2200	Suspended
0.6761	Remote Similarity	NPD6674	Discontinued
0.6758	Remote Similarity	NPD4678	Approved
0.6758	Remote Similarity	NPD4675	Approved
0.6754	Remote Similarity	NPD5313	Approved
0.6754	Remote Similarity	NPD5312	Approved
0.675	Remote Similarity	NPD5582	Discontinued
0.6749	Remote Similarity	NPD4482	Phase 3
0.6746	Remote Similarity	NPD5752	Clinical (unspecified phase)
0.6743	Remote Similarity	NPD2029	Clinical (unspecified phase)
0.6729	Remote Similarity	NPD8155	Clinical (unspecified phase)
0.672	Remote Similarity	NPD6688	Approved
0.672	Remote Similarity	NPD6687	Approved
0.6719	Remote Similarity	NPD7479	Phase 2
0.6705	Remote Similarity	NPD1372	Clinical (unspecified phase)
0.6705	Remote Similarity	NPD2492	Phase 1
0.6705	Remote Similarity	NPD2653	Approved
0.6705	Remote Similarity	NPD2568	Approved
0.6704	Remote Similarity	NPD5297	Approved
0.6703	Remote Similarity	NPD2358	Clinical (unspecified phase)
0.6703	Remote Similarity	NPD5977	Approved
0.6703	Remote Similarity	NPD5978	Approved
0.6703	Remote Similarity	NPD6523	Clinical (unspecified phase)
0.6702	Remote Similarity	NPD7228	Approved
0.6667	Remote Similarity	NPD3157	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