NPASS Compound

Structure

NPC473499 OpenBabel07101718202D 24 27 0 0 1 0 0 0 0 0999 V2000 -5.1962 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 1.5000 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 -0.8660 -1.5000 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 -4.3301 -0.5000 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 1.7321 -0.0000 0.0000 C 0 0 0 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 0.0000 1.0000 0.0000 C 0 0 3 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 -0.5000 0.0000 C 0 0 0 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 0.0000 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -0.5000 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 -0.8660 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 4 2 0 0 0 0 1 7 1 0 0 0 0 2 5 2 0 0 0 0 2 8 1 0 0 0 0 3 6 2 0 0 0 0 3 9 1 0 0 0 0 4 12 1 0 0 0 0 5 12 1 0 0 0 0 6 13 1 0 0 0 0 7 15 2 0 0 0 0 8 17 2 0 0 0 0 9 18 2 0 0 0 0 10 11 1 0 0 0 0 10 14 1 0 0 0 0 11 16 1 0 0 0 0 12 19 2 0 0 0 0 13 14 1 0 0 0 0 13 20 2 0 0 0 0 14 21 2 0 0 0 0 15 19 1 0 0 0 0 15 22 1 0 0 0 0 16 20 1 0 0 0 0 16 23 1 0 0 0 0 17 19 1 0 0 0 0 17 24 1 0 0 0 0 18 20 1 0 0 0 0 18 24 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	320.1
Volume:	331.683
LogP:	3.555
LogD:	3.066
LogS:	-4.611
# Rotatable Bonds:	2
TPSA:	66.76
# H-Bond Aceptor:	4
# H-Bond Donor:	2
# Rings:	4
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.737
Synthetic Accessibility Score:	2.931
Fsp3:	0.15
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
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:	-4.99
MDCK Permeability:	1.7631267837714404e-05
Pgp-inhibitor:	0.011
Pgp-substrate:	0.004
Human Intestinal Absorption (HIA):	0.026
20% Bioavailability (F20%):	0.948
30% Bioavailability (F30%):	0.997

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.196
Plasma Protein Binding (PPB):	97.24649810791016%
Volume Distribution (VD):	0.482
Pgp-substrate:	1.4159345626831055%

ADMET: Metabolism

CYP1A2-inhibitor:	0.965
CYP1A2-substrate:	0.526
CYP2C19-inhibitor:	0.884
CYP2C19-substrate:	0.094
CYP2C9-inhibitor:	0.787
CYP2C9-substrate:	0.906
CYP2D6-inhibitor:	0.665
CYP2D6-substrate:	0.869
CYP3A4-inhibitor:	0.29
CYP3A4-substrate:	0.333

ADMET: Excretion

Clearance (CL):	5.782
Half-life (T1/2):	0.568

ADMET: Toxicity

hERG Blockers:	0.031
Human Hepatotoxicity (H-HT):	0.025
Drug-inuced Liver Injury (DILI):	0.186
AMES Toxicity:	0.599
Rat Oral Acute Toxicity:	0.132
Maximum Recommended Daily Dose:	0.674
Skin Sensitization:	0.811
Carcinogencity:	0.823
Eye Corrosion:	0.003
Eye Irritation:	0.842
Respiratory Toxicity:	0.434

Download Data

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

Natural Product: NPC473499

Natural Product ID:	NPC473499
*Common Name:**	Decaspirone I
IUPAC Name:	4-hydroxy-5-(8-hydroxynaphthalen-1-yl)oxy-3,4-dihydro-2H-naphthalen-1-one
Synonyms:	Decaspirone I
Standard InCHIKey:	SQNMNCMAWPMNRM-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C20H16O4/c21-14-10-11-16(23)20-13(14)6-3-9-18(20)24-17-8-2-5-12-4-1-7-15(22)19(12)17/h1-9,16,22-23H,10-11H2
SMILES:	C1CC(=O)C2=C(C1O)C(=CC=C2)OC3=CC=CC4=C3C(=CC=C4)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL443870
PubChem CID:	16099379
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0000023] Naphthalenes [CHEMONTID:0002441] Naphthols 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
NPO33005	helicoma viridis	Species	Tubeufiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17190440]

☑ 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
Others	1

Activity Type	# Activity
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT18	Organism	Pseudomonas aeruginosa	Pseudomonas aeruginosa	IZ	=	8.0	mm	PMID[531581]

☑ 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 NPC473499 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	357
0.1-0.2	1583
0.2-0.3	3812
0.3-0.4	10520
0.4-0.5	7819
0.5-0.6	3723
0.6-0.7	6922
0.7-0.8	7520
0.8-0.85	417
0.85-0.9	22
0.9-0.95	1
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.8881	High Similarity	NPC306816
0.8828	High Similarity	NPC77903
0.8828	High Similarity	NPC17101
0.8819	High Similarity	NPC47152
0.8759	High Similarity	NPC301949
0.869	High Similarity	NPC97662
0.8639	High Similarity	NPC106328
0.8639	High Similarity	NPC35150
0.8618	High Similarity	NPC226287
0.8611	High Similarity	NPC133585
0.8611	High Similarity	NPC197461
0.8581	High Similarity	NPC474591
0.8552	High Similarity	NPC257404
0.8507	High Similarity	NPC217756
0.8506	High Similarity	NPC73148
0.8497	Intermediate Similarity	NPC195167
0.8487	Intermediate Similarity	NPC469507
0.8483	Intermediate Similarity	NPC69755
0.8446	Intermediate Similarity	NPC150215
0.8442	Intermediate Similarity	NPC292863
0.8442	Intermediate Similarity	NPC184326
0.844	Intermediate Similarity	NPC274876
0.8435	Intermediate Similarity	NPC473951
0.8435	Intermediate Similarity	NPC478019
0.8425	Intermediate Similarity	NPC3732
0.8411	Intermediate Similarity	NPC474843
0.8397	Intermediate Similarity	NPC290160
0.8387	Intermediate Similarity	NPC18380
0.8387	Intermediate Similarity	NPC137232
0.8378	Intermediate Similarity	NPC469758
0.8378	Intermediate Similarity	NPC206579
0.8378	Intermediate Similarity	NPC11800
0.8377	Intermediate Similarity	NPC324736
0.8377	Intermediate Similarity	NPC183402
0.8369	Intermediate Similarity	NPC138940
0.8355	Intermediate Similarity	NPC303950
0.8344	Intermediate Similarity	NPC39819
0.8344	Intermediate Similarity	NPC149085
0.8333	Intermediate Similarity	NPC470841
0.8322	Intermediate Similarity	NPC478163
0.8322	Intermediate Similarity	NPC478018
0.8322	Intermediate Similarity	NPC71055
0.8311	Intermediate Similarity	NPC469764
0.8301	Intermediate Similarity	NPC254351
0.8301	Intermediate Similarity	NPC66508
0.8301	Intermediate Similarity	NPC226656
0.8289	Intermediate Similarity	NPC207624
0.8289	Intermediate Similarity	NPC154683
0.8289	Intermediate Similarity	NPC40356
0.8286	Intermediate Similarity	NPC7569
0.8278	Intermediate Similarity	NPC13282
0.8278	Intermediate Similarity	NPC475890
0.8269	Intermediate Similarity	NPC472261
0.8261	Intermediate Similarity	NPC85368
0.8258	Intermediate Similarity	NPC193749
0.8258	Intermediate Similarity	NPC55443
0.8258	Intermediate Similarity	NPC18699
0.8258	Intermediate Similarity	NPC186113
0.8255	Intermediate Similarity	NPC300540
0.8248	Intermediate Similarity	NPC193805
0.8247	Intermediate Similarity	NPC208152
0.8247	Intermediate Similarity	NPC78492
0.8247	Intermediate Similarity	NPC137100
0.8247	Intermediate Similarity	NPC309648
0.8239	Intermediate Similarity	NPC470406
0.8235	Intermediate Similarity	NPC135522
0.8235	Intermediate Similarity	NPC329844
0.8231	Intermediate Similarity	NPC49108
0.8228	Intermediate Similarity	NPC469664
0.8227	Intermediate Similarity	NPC141549
0.8224	Intermediate Similarity	NPC106372
0.8224	Intermediate Similarity	NPC474417
0.8224	Intermediate Similarity	NPC149526
0.8224	Intermediate Similarity	NPC23668
0.8224	Intermediate Similarity	NPC115324
0.8224	Intermediate Similarity	NPC470569
0.8224	Intermediate Similarity	NPC58668
0.8224	Intermediate Similarity	NPC193976
0.8224	Intermediate Similarity	NPC72958
0.8224	Intermediate Similarity	NPC232645
0.8217	Intermediate Similarity	NPC3448
0.8217	Intermediate Similarity	NPC261896
0.8217	Intermediate Similarity	NPC477239
0.8214	Intermediate Similarity	NPC238309
0.8212	Intermediate Similarity	NPC65775
0.8212	Intermediate Similarity	NPC10027
0.8194	Intermediate Similarity	NPC141934
0.8194	Intermediate Similarity	NPC67197
0.8188	Intermediate Similarity	NPC470135
0.8188	Intermediate Similarity	NPC39045
0.8188	Intermediate Similarity	NPC131766
0.8188	Intermediate Similarity	NPC470136
0.8182	Intermediate Similarity	NPC300668
0.8182	Intermediate Similarity	NPC201227
0.8182	Intermediate Similarity	NPC478161
0.8182	Intermediate Similarity	NPC99199
0.8182	Intermediate Similarity	NPC66441
0.8182	Intermediate Similarity	NPC182555
0.8182	Intermediate Similarity	NPC134171
0.8182	Intermediate Similarity	NPC57141
0.8182	Intermediate Similarity	NPC478159
0.8182	Intermediate Similarity	NPC148938
0.8182	Intermediate Similarity	NPC258474
0.8176	Intermediate Similarity	NPC310340
0.817	Intermediate Similarity	NPC142308
0.817	Intermediate Similarity	NPC281272
0.817	Intermediate Similarity	NPC174086
0.817	Intermediate Similarity	NPC474656
0.817	Intermediate Similarity	NPC87708
0.8169	Intermediate Similarity	NPC470160
0.8163	Intermediate Similarity	NPC145673
0.8163	Intermediate Similarity	NPC149780
0.8158	Intermediate Similarity	NPC290954
0.8158	Intermediate Similarity	NPC255641
0.8158	Intermediate Similarity	NPC225854
0.8158	Intermediate Similarity	NPC470568
0.8158	Intermediate Similarity	NPC93619
0.8158	Intermediate Similarity	NPC295036
0.8156	Intermediate Similarity	NPC278787
0.8153	Intermediate Similarity	NPC96031
0.8151	Intermediate Similarity	NPC18457
0.8151	Intermediate Similarity	NPC470407
0.8151	Intermediate Similarity	NPC112757
0.8151	Intermediate Similarity	NPC86744
0.8151	Intermediate Similarity	NPC1268
0.8146	Intermediate Similarity	NPC472841
0.8146	Intermediate Similarity	NPC122894
0.8141	Intermediate Similarity	NPC15815
0.8137	Intermediate Similarity	NPC313304
0.8133	Intermediate Similarity	NPC470133
0.8133	Intermediate Similarity	NPC308799
0.8133	Intermediate Similarity	NPC473078
0.8133	Intermediate Similarity	NPC470131
0.8133	Intermediate Similarity	NPC299011
0.8133	Intermediate Similarity	NPC470132
0.8133	Intermediate Similarity	NPC109183
0.8133	Intermediate Similarity	NPC60389
0.8133	Intermediate Similarity	NPC211565
0.8133	Intermediate Similarity	NPC470134
0.8129	Intermediate Similarity	NPC69531
0.8129	Intermediate Similarity	NPC32867
0.8129	Intermediate Similarity	NPC198489
0.8129	Intermediate Similarity	NPC61112
0.8129	Intermediate Similarity	NPC279605
0.8125	Intermediate Similarity	NPC103633
0.8117	Intermediate Similarity	NPC121568
0.8117	Intermediate Similarity	NPC235333
0.8117	Intermediate Similarity	NPC474000
0.8117	Intermediate Similarity	NPC210942
0.8117	Intermediate Similarity	NPC475770
0.8117	Intermediate Similarity	NPC169990
0.8113	Intermediate Similarity	NPC297404
0.8113	Intermediate Similarity	NPC11608
0.811	Intermediate Similarity	NPC475783
0.8108	Intermediate Similarity	NPC103752
0.8108	Intermediate Similarity	NPC329493
0.8105	Intermediate Similarity	NPC478148
0.8105	Intermediate Similarity	NPC476552
0.8105	Intermediate Similarity	NPC476553
0.8105	Intermediate Similarity	NPC204561
0.8105	Intermediate Similarity	NPC316960
0.8105	Intermediate Similarity	NPC148945
0.8105	Intermediate Similarity	NPC309512
0.8105	Intermediate Similarity	NPC230848
0.8105	Intermediate Similarity	NPC317715
0.8105	Intermediate Similarity	NPC178484
0.8105	Intermediate Similarity	NPC78835
0.8105	Intermediate Similarity	NPC476551
0.8101	Intermediate Similarity	NPC473961
0.8101	Intermediate Similarity	NPC15374
0.8101	Intermediate Similarity	NPC146837
0.8101	Intermediate Similarity	NPC101116
0.8101	Intermediate Similarity	NPC278329
0.8101	Intermediate Similarity	NPC212099
0.8101	Intermediate Similarity	NPC249070
0.8099	Intermediate Similarity	NPC137264
0.8095	Intermediate Similarity	NPC477537
0.8092	Intermediate Similarity	NPC158338
0.8092	Intermediate Similarity	NPC3642
0.8092	Intermediate Similarity	NPC100985
0.8092	Intermediate Similarity	NPC132345
0.8092	Intermediate Similarity	NPC288036
0.8092	Intermediate Similarity	NPC97028
0.8092	Intermediate Similarity	NPC97029
0.8092	Intermediate Similarity	NPC65589
0.8092	Intermediate Similarity	NPC474052
0.8089	Intermediate Similarity	NPC24164
0.8089	Intermediate Similarity	NPC284495
0.8089	Intermediate Similarity	NPC472902
0.8089	Intermediate Similarity	NPC472618
0.8089	Intermediate Similarity	NPC186325
0.8082	Intermediate Similarity	NPC275055
0.8082	Intermediate Similarity	NPC290291
0.8082	Intermediate Similarity	NPC188879
0.8079	Intermediate Similarity	NPC113428
0.8079	Intermediate Similarity	NPC61284
0.8079	Intermediate Similarity	NPC259632
0.8079	Intermediate Similarity	NPC12305
0.8077	Intermediate Similarity	NPC475184
0.8077	Intermediate Similarity	NPC96342

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 NPC473499 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	330
0.1-0.2	970
0.2-0.3	1374
0.3-0.4	2492
0.4-0.5	1984
0.5-0.6	1245
0.6-0.7	573
0.7-0.8	172
0.8-0.85	9
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8707	High Similarity	NPD5808	Clinical (unspecified phase)
0.8288	Intermediate Similarity	NPD3750	Approved
0.8153	Intermediate Similarity	NPD6959	Discontinued
0.8067	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.8027	Intermediate Similarity	NPD1549	Phase 2
0.8013	Intermediate Similarity	NPD6273	Approved
0.8013	Intermediate Similarity	NPD7768	Phase 2
0.8013	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7963	Intermediate Similarity	NPD5844	Phase 1
0.7962	Intermediate Similarity	NPD3749	Approved
0.7959	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7959	Intermediate Similarity	NPD2346	Discontinued
0.7959	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7949	Intermediate Similarity	NPD5402	Approved
0.7949	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7945	Intermediate Similarity	NPD3748	Approved
0.7929	Intermediate Similarity	NPD1203	Approved
0.7919	Intermediate Similarity	NPD7003	Approved
0.7899	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7885	Intermediate Similarity	NPD7819	Suspended
0.7852	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7843	Intermediate Similarity	NPD5403	Approved
0.7838	Intermediate Similarity	NPD2344	Approved
0.7831	Intermediate Similarity	NPD8313	Approved
0.7831	Intermediate Similarity	NPD8312	Approved
0.7829	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7823	Intermediate Similarity	NPD1510	Phase 2
0.7806	Intermediate Similarity	NPD4380	Phase 2
0.7801	Intermediate Similarity	NPD2797	Approved
0.7778	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD2313	Discontinued
0.7778	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD3268	Approved
0.7778	Intermediate Similarity	NPD6166	Phase 2
0.7771	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.777	Intermediate Similarity	NPD2796	Approved
0.777	Intermediate Similarity	NPD2935	Discontinued
0.777	Intermediate Similarity	NPD1551	Phase 2
0.7762	Intermediate Similarity	NPD6832	Phase 2
0.7758	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7756	Intermediate Similarity	NPD7411	Suspended
0.7742	Intermediate Similarity	NPD3226	Approved
0.7736	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7718	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7712	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7712	Intermediate Similarity	NPD5401	Approved
0.7707	Intermediate Similarity	NPD6844	Discontinued
0.7707	Intermediate Similarity	NPD1934	Approved
0.7703	Intermediate Similarity	NPD4308	Phase 3
0.7703	Intermediate Similarity	NPD2799	Discontinued
0.7683	Intermediate Similarity	NPD3751	Discontinued
0.7676	Intermediate Similarity	NPD1470	Approved
0.7673	Intermediate Similarity	NPD3882	Suspended
0.7658	Intermediate Similarity	NPD2801	Approved
0.7655	Intermediate Similarity	NPD3764	Approved
0.7654	Intermediate Similarity	NPD3787	Discontinued
0.7651	Intermediate Similarity	NPD5404	Approved
0.7651	Intermediate Similarity	NPD5406	Approved
0.7651	Intermediate Similarity	NPD5405	Approved
0.7651	Intermediate Similarity	NPD5408	Approved
0.7647	Intermediate Similarity	NPD1511	Approved
0.7639	Intermediate Similarity	NPD4908	Phase 1
0.7632	Intermediate Similarity	NPD2309	Approved
0.7628	Intermediate Similarity	NPD2651	Approved
0.7628	Intermediate Similarity	NPD2649	Approved
0.7622	Intermediate Similarity	NPD2798	Approved
0.7619	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7589	Intermediate Similarity	NPD9717	Approved
0.7576	Intermediate Similarity	NPD7177	Discontinued
0.7576	Intermediate Similarity	NPD3818	Discontinued
0.7566	Intermediate Similarity	NPD4628	Phase 3
0.7566	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7551	Intermediate Similarity	NPD1240	Approved
0.755	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7548	Intermediate Similarity	NPD1512	Approved
0.7547	Intermediate Similarity	NPD1465	Phase 2
0.7546	Intermediate Similarity	NPD6232	Discontinued
0.7534	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7534	Intermediate Similarity	NPD6798	Discontinued
0.7533	Intermediate Similarity	NPD6100	Approved
0.7533	Intermediate Similarity	NPD6099	Approved
0.7518	Intermediate Similarity	NPD1201	Approved
0.7516	Intermediate Similarity	NPD7075	Discontinued
0.7515	Intermediate Similarity	NPD7473	Discontinued
0.75	Intermediate Similarity	NPD6559	Discontinued
0.75	Intermediate Similarity	NPD447	Suspended
0.7483	Intermediate Similarity	NPD3225	Approved
0.7466	Intermediate Similarity	NPD4625	Phase 3
0.7464	Intermediate Similarity	NPD405	Clinical (unspecified phase)
0.7451	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.745	Intermediate Similarity	NPD1607	Approved
0.7438	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7432	Intermediate Similarity	NPD4307	Phase 2
0.7431	Intermediate Similarity	NPD3267	Approved
0.7431	Intermediate Similarity	NPD3266	Approved
0.7425	Intermediate Similarity	NPD7054	Approved
0.7423	Intermediate Similarity	NPD5494	Approved
0.7419	Intermediate Similarity	NPD7390	Discontinued
0.7419	Intermediate Similarity	NPD6799	Approved
0.7415	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7415	Intermediate Similarity	NPD411	Approved
0.7405	Intermediate Similarity	NPD7458	Discontinued
0.7391	Intermediate Similarity	NPD5616	Clinical (unspecified phase)
0.7381	Intermediate Similarity	NPD7074	Phase 3
0.7381	Intermediate Similarity	NPD7472	Approved
0.7375	Intermediate Similarity	NPD6801	Discontinued
0.7372	Intermediate Similarity	NPD1241	Discontinued
0.7365	Intermediate Similarity	NPD6233	Phase 2
0.7361	Intermediate Similarity	NPD1876	Approved
0.7355	Intermediate Similarity	NPD7440	Discontinued
0.7353	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7351	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7337	Intermediate Similarity	NPD6797	Phase 2
0.7329	Intermediate Similarity	NPD8455	Phase 2
0.7315	Intermediate Similarity	NPD4060	Phase 1
0.7314	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7305	Intermediate Similarity	NPD1651	Approved
0.7301	Intermediate Similarity	NPD8005	Clinical (unspecified phase)
0.7299	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7294	Intermediate Similarity	NPD7251	Discontinued
0.7284	Intermediate Similarity	NPD3817	Phase 2
0.7284	Intermediate Similarity	NPD4288	Approved
0.7273	Intermediate Similarity	NPD1610	Phase 2
0.7267	Intermediate Similarity	NPD6355	Discontinued
0.7267	Intermediate Similarity	NPD1933	Approved
0.7261	Intermediate Similarity	NPD2534	Approved
0.7261	Intermediate Similarity	NPD2532	Approved
0.7261	Intermediate Similarity	NPD2533	Approved
0.7251	Intermediate Similarity	NPD7808	Phase 3
0.725	Intermediate Similarity	NPD6599	Discontinued
0.7241	Intermediate Similarity	NPD1283	Approved
0.7237	Intermediate Similarity	NPD7033	Discontinued
0.7234	Intermediate Similarity	NPD1548	Phase 1
0.723	Intermediate Similarity	NPD7008	Discontinued
0.7229	Intermediate Similarity	NPD7229	Phase 3
0.7222	Intermediate Similarity	NPD3972	Approved
0.7222	Intermediate Similarity	NPD1608	Approved
0.7219	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7214	Intermediate Similarity	NPD9493	Approved
0.7211	Intermediate Similarity	NPD2861	Phase 2
0.7209	Intermediate Similarity	NPD7546	Discontinued
0.7203	Intermediate Similarity	NPD3496	Discontinued
0.72	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.72	Intermediate Similarity	NPD1613	Approved
0.719	Intermediate Similarity	NPD4477	Approved
0.719	Intermediate Similarity	NPD4476	Approved
0.7172	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.717	Intermediate Similarity	NPD7427	Discontinued
0.7169	Intermediate Similarity	NPD7199	Phase 2
0.716	Intermediate Similarity	NPD7577	Discontinued
0.716	Intermediate Similarity	NPD37	Approved
0.7152	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD4661	Approved
0.7152	Intermediate Similarity	NPD4662	Approved
0.7143	Intermediate Similarity	NPD1471	Phase 3
0.7143	Intermediate Similarity	NPD1019	Discontinued
0.7134	Intermediate Similarity	NPD4966	Approved
0.7134	Intermediate Similarity	NPD4965	Approved
0.7134	Intermediate Similarity	NPD4967	Phase 2
0.7124	Intermediate Similarity	NPD3299	Clinical (unspecified phase)
0.7115	Intermediate Similarity	NPD8166	Discontinued
0.7113	Intermediate Similarity	NPD1894	Discontinued
0.7103	Intermediate Similarity	NPD1481	Phase 2
0.7097	Intermediate Similarity	NPD2897	Discontinued
0.7097	Intermediate Similarity	NPD2424	Discontinued
0.7095	Intermediate Similarity	NPD9494	Approved
0.7086	Intermediate Similarity	NPD943	Approved
0.7086	Intermediate Similarity	NPD2979	Phase 3
0.7086	Intermediate Similarity	NPD4140	Approved
0.7083	Intermediate Similarity	NPD3926	Phase 2
0.7078	Intermediate Similarity	NPD2438	Suspended
0.7076	Intermediate Similarity	NPD5441	Clinical (unspecified phase)
0.7073	Intermediate Similarity	NPD2296	Approved
0.7067	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7066	Intermediate Similarity	NPD8127	Discontinued
0.7063	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7063	Intermediate Similarity	NPD5585	Approved
0.7055	Intermediate Similarity	NPD4749	Approved
0.7055	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7051	Intermediate Similarity	NPD2800	Approved
0.7048	Intermediate Similarity	NPD6234	Discontinued
0.7044	Intermediate Similarity	NPD7446	Clinical (unspecified phase)
0.7041	Intermediate Similarity	NPD4575	Clinical (unspecified phase)
0.7034	Intermediate Similarity	NPD1281	Approved
0.7034	Intermediate Similarity	NPD1535	Discovery
0.7033	Intermediate Similarity	NPD6780	Approved
0.7033	Intermediate Similarity	NPD6777	Approved
0.7033	Intermediate Similarity	NPD6782	Approved
0.7033	Intermediate Similarity	NPD6779	Approved
0.7033	Intermediate Similarity	NPD6781	Approved
0.7033	Intermediate Similarity	NPD6778	Approved
0.7033	Intermediate Similarity	NPD6776	Approved
0.7027	Intermediate Similarity	NPD5647	Approved
0.7027	Intermediate Similarity	NPD6584	Phase 3
0.7021	Intermediate Similarity	NPD6671	Approved
0.702	Intermediate Similarity	NPD8032	Phase 2
0.7014	Intermediate Similarity	NPD4626	Approved
0.7014	Intermediate Similarity	NPD17	Approved
0.7014	Intermediate Similarity	NPD1778	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