NPASS Compound

Structure

CID63190 OpenBabel06191715402D 22 25 0 0 1 0 0 0 0 0999 V2000 -1.5170 -0.8498 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8506 2.0496 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0339 -0.0001 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0001 -1.7517 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7584 -1.3138 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7585 1.3137 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2755 -0.4380 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0340 0.8758 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 0.8758 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7585 -0.4379 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8759 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8377 -0.5553 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7586 -1.3138 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.5170 0.8758 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.7585 -0.4379 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.5170 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.2755 1.3137 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.0000 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.1965 -0.5553 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.9710 0.0719 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.7004 2.0496 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.6181 -1.2855 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3 7 1 0 0 0 0 3 8 1 0 0 0 0 4 5 1 0 0 0 0 4 13 1 0 0 0 0 5 15 1 0 0 0 0 6 9 1 0 0 0 0 6 14 1 0 0 0 0 7 16 1 0 0 0 0 8 17 1 0 0 0 0 10 13 1 0 0 0 0 10 18 1 0 0 0 0 11 18 1 0 0 0 0 11 19 1 0 0 0 0 12 19 1 0 0 0 0 12 20 1 0 0 0 0 13 19 1 1 0 0 0 14 16 1 1 0 0 0 14 17 1 0 0 0 0 15 16 1 1 0 0 0 15 18 1 0 0 0 0 16 1 1 1 0 0 0 17 2 1 6 0 0 0 17 21 1 0 0 0 0 18 9 1 1 0 0 0 19 22 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	308.24
Volume:	329.325
LogP:	2.763
LogD:	2.261
LogS:	-2.882
# Rotatable Bonds:	1
TPSA:	60.69
# H-Bond Aceptor:	3
# H-Bond Donor:	3
# Rings:	4
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.698
Synthetic Accessibility Score:	5.749
Fsp3:	1.0
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:	-5.273
MDCK Permeability:	1.1844997061416507e-05
Pgp-inhibitor:	0.012
Pgp-substrate:	0.069
Human Intestinal Absorption (HIA):	0.005
20% Bioavailability (F20%):	0.042
30% Bioavailability (F30%):	0.982

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.38
Plasma Protein Binding (PPB):	66.46231842041016%
Volume Distribution (VD):	1.012
Pgp-substrate:	19.350204467773438%

ADMET: Metabolism

CYP1A2-inhibitor:	0.01
CYP1A2-substrate:	0.741
CYP2C19-inhibitor:	0.016
CYP2C19-substrate:	0.712
CYP2C9-inhibitor:	0.042
CYP2C9-substrate:	0.062
CYP2D6-inhibitor:	0.009
CYP2D6-substrate:	0.114
CYP3A4-inhibitor:	0.939
CYP3A4-substrate:	0.154

ADMET: Excretion

Clearance (CL):	6.914
Half-life (T1/2):	0.283

ADMET: Toxicity

hERG Blockers:	0.038
Human Hepatotoxicity (H-HT):	0.648
Drug-inuced Liver Injury (DILI):	0.026
AMES Toxicity:	0.007
Rat Oral Acute Toxicity:	0.044
Maximum Recommended Daily Dose:	0.742
Skin Sensitization:	0.847
Carcinogencity:	0.914
Eye Corrosion:	0.065
Eye Irritation:	0.156
Respiratory Toxicity:	0.945

Download Data

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

Natural Product: NPC63190

Natural Product ID:	NPC63190
*Common Name:**	Annosquamosin B
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	NICDFCNOCPZHTJ-LXGSHKTASA-N
Standard InCHI:	InChI=1S/C19H32O3/c1-16-7-3-8-17(2,21)14(16)6-9-18-10-13(4-5-15(16)18)19(22,11-18)12-20/h13-15,20-22H,3-12H2,1-2H3/t13-,14-,15-,16+,17+,18-,19+/m0/s1
SMILES:	OC[C@]1(O)C[C@@]23C[C@@H]1CC[C@H]3[C@]1([C@H](CC2)[C@](C)(O)CCC1)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL516819
PubChem CID:	44566886
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001551] Diterpenoids [CHEMONTID:0003782] Kaurane diterpenoids

*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
NPO2884	Annona squamosa	Species	Annonaceae	Eukaryota	seeds	n.a.	n.a.	PMID[11141125]
NPO2884	Annona squamosa	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12398544]
NPO2884	Annona squamosa	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18419154]
NPO2884	Annona squamosa	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19296389]
NPO2884	Annona squamosa	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21910504]
NPO2884	Annona squamosa	Species	Annonaceae	Eukaryota	n.a.	seed	n.a.	PMID[22011319]
NPO2884	Annona squamosa	Species	Annonaceae	Eukaryota	seeds	n.a.	n.a.	PMID[22011319]
NPO2884	Annona squamosa	Species	Annonaceae	Eukaryota	Barks	n.a.	n.a.	PMID[2348205]
NPO2884	Annona squamosa	Species	Annonaceae	Eukaryota	n.a.	fruit	n.a.	PMID[8786370]
NPO2884	Annona squamosa	Species	Annonaceae	Eukaryota	bark	n.a.	n.a.	PMID[9214729]
NPO2884	Annona squamosa	Species	Annonaceae	Eukaryota	Fruit	n.a.	n.a.	Database[FooDB]
NPO2884	Annona squamosa	Species	Annonaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO2884	Annona squamosa	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO2884	Annona squamosa	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO2884	Annona squamosa	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO2884	Annona squamosa	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
Others	4

Activity Type	# Activity
NON-MOLECULAR	4

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Inhibition	=	8.7	%	PMID[509226]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Inhibition	=	21.1	%	PMID[509226]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Inhibition	=	8.5	%	PMID[509226]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Inhibition	=	1.6	%	PMID[509226]

☑ 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 NPC63190 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	369
0.1-0.2	4834
0.2-0.3	17965
0.3-0.4	8054
0.4-0.5	4816
0.5-0.6	4276
0.6-0.7	1818
0.7-0.8	433
0.8-0.85	57
0.85-0.9	59
0.9-0.95	11
0.95-1	5

Similarity Score	Similarity Level	Natural Product ID
0.9677	High Similarity	NPC475943
0.9677	High Similarity	NPC190827
0.9677	High Similarity	NPC243469
0.9254	High Similarity	NPC153719
0.9091	High Similarity	NPC107919
0.9091	High Similarity	NPC470830
0.9091	High Similarity	NPC241085
0.9091	High Similarity	NPC299948
0.8986	High Similarity	NPC317242
0.8971	High Similarity	NPC470610
0.8955	High Similarity	NPC231945
0.8923	High Similarity	NPC44122
0.8906	High Similarity	NPC118937
0.8906	High Similarity	NPC281540
0.8906	High Similarity	NPC167995
0.8906	High Similarity	NPC159654
0.8857	High Similarity	NPC470145
0.8857	High Similarity	NPC163597
0.8841	High Similarity	NPC48795
0.8806	High Similarity	NPC477820
0.8788	High Similarity	NPC48079
0.875	High Similarity	NPC114891
0.8732	High Similarity	NPC105208
0.8732	High Similarity	NPC171658
0.8732	High Similarity	NPC477227
0.8732	High Similarity	NPC302578
0.8732	High Similarity	NPC128951
0.8732	High Similarity	NPC192046
0.8732	High Similarity	NPC185915
0.871	High Similarity	NPC476735
0.8696	High Similarity	NPC473238
0.8696	High Similarity	NPC472341
0.8676	High Similarity	NPC63588
0.8676	High Similarity	NPC232925
0.8676	High Similarity	NPC251201
0.8657	High Similarity	NPC472741
0.8636	High Similarity	NPC142712
0.8611	High Similarity	NPC18857
0.8611	High Similarity	NPC67657
0.8594	High Similarity	NPC71460
0.8594	High Similarity	NPC218585
0.8594	High Similarity	NPC148174
0.8571	High Similarity	NPC10476
0.8571	High Similarity	NPC472854
0.8571	High Similarity	NPC228994
0.8571	High Similarity	NPC477508
0.8571	High Similarity	NPC192501
0.8571	High Similarity	NPC304499
0.8551	High Similarity	NPC157777
0.8551	High Similarity	NPC131506
0.8529	High Similarity	NPC254037
0.8529	High Similarity	NPC129829
0.8529	High Similarity	NPC66407
0.8507	High Similarity	NPC473230
0.8507	High Similarity	NPC475884
0.8493	Intermediate Similarity	NPC287452
0.8485	Intermediate Similarity	NPC474380
0.8485	Intermediate Similarity	NPC41577
0.8485	Intermediate Similarity	NPC472946
0.8485	Intermediate Similarity	NPC260116
0.8485	Intermediate Similarity	NPC473276
0.8451	Intermediate Similarity	NPC231680
0.8451	Intermediate Similarity	NPC27349
0.8451	Intermediate Similarity	NPC196136
0.8451	Intermediate Similarity	NPC91387
0.8451	Intermediate Similarity	NPC158208
0.8451	Intermediate Similarity	NPC270306
0.8451	Intermediate Similarity	NPC243027
0.8451	Intermediate Similarity	NPC24014
0.8406	Intermediate Similarity	NPC192192
0.8406	Intermediate Similarity	NPC282454
0.8387	Intermediate Similarity	NPC3025
0.8382	Intermediate Similarity	NPC474756
0.8333	Intermediate Similarity	NPC69149
0.8333	Intermediate Similarity	NPC91573
0.8286	Intermediate Similarity	NPC100586
0.8286	Intermediate Similarity	NPC157422
0.8286	Intermediate Similarity	NPC252182
0.8286	Intermediate Similarity	NPC109457
0.8286	Intermediate Similarity	NPC127283
0.8286	Intermediate Similarity	NPC470071
0.8286	Intermediate Similarity	NPC127094
0.8286	Intermediate Similarity	NPC195530
0.8286	Intermediate Similarity	NPC8004
0.8286	Intermediate Similarity	NPC1340
0.8286	Intermediate Similarity	NPC187471
0.8286	Intermediate Similarity	NPC473279
0.8261	Intermediate Similarity	NPC99264
0.8254	Intermediate Similarity	NPC135438
0.8219	Intermediate Similarity	NPC64081
0.8219	Intermediate Similarity	NPC474574
0.8219	Intermediate Similarity	NPC180199
0.8219	Intermediate Similarity	NPC476233
0.8219	Intermediate Similarity	NPC133596
0.8219	Intermediate Similarity	NPC11907
0.8219	Intermediate Similarity	NPC477919
0.8182	Intermediate Similarity	NPC249078
0.8182	Intermediate Similarity	NPC236099
0.8182	Intermediate Similarity	NPC209686
0.8158	Intermediate Similarity	NPC475388
0.8125	Intermediate Similarity	NPC162685
0.8116	Intermediate Similarity	NPC475893
0.8108	Intermediate Similarity	NPC476732
0.8108	Intermediate Similarity	NPC147993
0.8108	Intermediate Similarity	NPC42853
0.8108	Intermediate Similarity	NPC471045
0.8108	Intermediate Similarity	NPC199965
0.8082	Intermediate Similarity	NPC477602
0.8082	Intermediate Similarity	NPC473916
0.8082	Intermediate Similarity	NPC477601
0.8052	Intermediate Similarity	NPC478054
0.8028	Intermediate Similarity	NPC478103
0.8	Intermediate Similarity	NPC269333
0.8	Intermediate Similarity	NPC49599
0.8	Intermediate Similarity	NPC95958
0.8	Intermediate Similarity	NPC49627
0.8	Intermediate Similarity	NPC81074
0.8	Intermediate Similarity	NPC477282
0.8	Intermediate Similarity	NPC470833
0.7971	Intermediate Similarity	NPC204233
0.7969	Intermediate Similarity	NPC236588
0.7945	Intermediate Similarity	NPC131584
0.7945	Intermediate Similarity	NPC3403
0.7945	Intermediate Similarity	NPC139765
0.7941	Intermediate Similarity	NPC80463
0.7922	Intermediate Similarity	NPC317066
0.7917	Intermediate Similarity	NPC232112
0.7917	Intermediate Similarity	NPC310766
0.7895	Intermediate Similarity	NPC16449
0.7895	Intermediate Similarity	NPC470609
0.7895	Intermediate Similarity	NPC13554
0.7867	Intermediate Similarity	NPC102708
0.7867	Intermediate Similarity	NPC472501
0.7867	Intermediate Similarity	NPC477819
0.7867	Intermediate Similarity	NPC477817
0.7848	Intermediate Similarity	NPC266651
0.7808	Intermediate Similarity	NPC478130
0.7808	Intermediate Similarity	NPC475458
0.7808	Intermediate Similarity	NPC476736
0.7792	Intermediate Similarity	NPC12933
0.7778	Intermediate Similarity	NPC156277
0.7778	Intermediate Similarity	NPC111234
0.7778	Intermediate Similarity	NPC58057
0.7778	Intermediate Similarity	NPC320549
0.7778	Intermediate Similarity	NPC151018
0.7763	Intermediate Similarity	NPC476176
0.7761	Intermediate Similarity	NPC95804
0.7761	Intermediate Similarity	NPC185547
0.775	Intermediate Similarity	NPC472272
0.775	Intermediate Similarity	NPC476726
0.775	Intermediate Similarity	NPC121981
0.775	Intermediate Similarity	NPC476727
0.7746	Intermediate Similarity	NPC321732
0.7746	Intermediate Similarity	NPC324607
0.7733	Intermediate Similarity	NPC138502
0.7733	Intermediate Similarity	NPC264602
0.7733	Intermediate Similarity	NPC307336
0.7733	Intermediate Similarity	NPC475031
0.7733	Intermediate Similarity	NPC23884
0.7733	Intermediate Similarity	NPC260301
0.7722	Intermediate Similarity	NPC255882
0.7703	Intermediate Similarity	NPC125767
0.7703	Intermediate Similarity	NPC21220
0.7703	Intermediate Similarity	NPC231256
0.7703	Intermediate Similarity	NPC185536
0.7703	Intermediate Similarity	NPC212879
0.7703	Intermediate Similarity	NPC104387
0.7703	Intermediate Similarity	NPC273366
0.7703	Intermediate Similarity	NPC240235
0.7703	Intermediate Similarity	NPC230704
0.7703	Intermediate Similarity	NPC174964
0.7703	Intermediate Similarity	NPC97534
0.7703	Intermediate Similarity	NPC195155
0.7703	Intermediate Similarity	NPC70982
0.7703	Intermediate Similarity	NPC178383
0.7703	Intermediate Similarity	NPC212733
0.7692	Intermediate Similarity	NPC470611
0.7692	Intermediate Similarity	NPC154043
0.7692	Intermediate Similarity	NPC202688
0.7692	Intermediate Similarity	NPC60018
0.7692	Intermediate Similarity	NPC150713
0.7692	Intermediate Similarity	NPC477935
0.7692	Intermediate Similarity	NPC29976
0.7671	Intermediate Similarity	NPC472506
0.7671	Intermediate Similarity	NPC81759
0.7662	Intermediate Similarity	NPC78545
0.7662	Intermediate Similarity	NPC472853
0.7662	Intermediate Similarity	NPC71535
0.7654	Intermediate Similarity	NPC210658
0.7654	Intermediate Similarity	NPC161928
0.7647	Intermediate Similarity	NPC290791
0.7647	Intermediate Similarity	NPC292419
0.7639	Intermediate Similarity	NPC45296
0.7632	Intermediate Similarity	NPC471769
0.7632	Intermediate Similarity	NPC472502
0.7632	Intermediate Similarity	NPC472499
0.7632	Intermediate Similarity	NPC475
0.7632	Intermediate Similarity	NPC472342
0.7632	Intermediate Similarity	NPC285761
0.7632	Intermediate Similarity	NPC31828

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 NPC63190 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	379
0.1-0.2	4480
0.2-0.3	3111
0.3-0.4	676
0.4-0.5	186
0.5-0.6	213
0.6-0.7	74
0.7-0.8	26
0.8-0.85	3
0.85-0.9	1
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9091	High Similarity	NPD4267	Clinical (unspecified phase)
0.8676	High Similarity	NPD4787	Phase 1
0.7887	Intermediate Similarity	NPD4244	Approved
0.7887	Intermediate Similarity	NPD4245	Approved
0.7778	Intermediate Similarity	NPD4808	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD4809	Clinical (unspecified phase)
0.7746	Intermediate Similarity	NPD3698	Phase 2
0.7639	Intermediate Similarity	NPD4789	Approved
0.7606	Intermediate Similarity	NPD5360	Phase 3
0.7606	Intermediate Similarity	NPD5361	Clinical (unspecified phase)
0.76	Intermediate Similarity	NPD6117	Approved
0.7568	Intermediate Similarity	NPD6113	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD3699	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD3700	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD6116	Phase 1
0.7436	Intermediate Similarity	NPD7525	Registered
0.7436	Intermediate Similarity	NPD6928	Phase 2
0.7429	Intermediate Similarity	NPD3171	Clinical (unspecified phase)
0.7403	Intermediate Similarity	NPD6118	Approved
0.7403	Intermediate Similarity	NPD6115	Approved
0.7403	Intermediate Similarity	NPD6114	Approved
0.7403	Intermediate Similarity	NPD6697	Approved
0.7237	Intermediate Similarity	NPD3703	Phase 2
0.7237	Intermediate Similarity	NPD3702	Approved
0.716	Intermediate Similarity	NPD4788	Approved
0.7123	Intermediate Similarity	NPD6705	Phase 1
0.7067	Intermediate Similarity	NPD4758	Discontinued
0.7067	Intermediate Similarity	NPD4243	Approved
0.7	Intermediate Similarity	NPD4748	Discontinued
0.6923	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD6933	Approved
0.6883	Remote Similarity	NPD4784	Approved
0.6883	Remote Similarity	NPD4785	Approved
0.6849	Remote Similarity	NPD4224	Phase 2
0.6842	Remote Similarity	NPD6081	Approved
0.6842	Remote Similarity	NPD5777	Approved
0.6818	Remote Similarity	NPD8171	Discontinued
0.6795	Remote Similarity	NPD7339	Approved
0.6795	Remote Similarity	NPD6942	Approved
0.6786	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.675	Remote Similarity	NPD3671	Phase 1
0.675	Remote Similarity	NPD5364	Discontinued
0.6667	Remote Similarity	NPD384	Approved
0.6667	Remote Similarity	NPD6924	Approved
0.6667	Remote Similarity	NPD385	Approved
0.6667	Remote Similarity	NPD6926	Approved
0.6582	Remote Similarity	NPD4190	Phase 3
0.6582	Remote Similarity	NPD5275	Approved
0.6463	Remote Similarity	NPD4195	Approved
0.6463	Remote Similarity	NPD7645	Phase 2
0.6444	Remote Similarity	NPD4202	Approved
0.6437	Remote Similarity	NPD4751	Clinical (unspecified phase)
0.6404	Remote Similarity	NPD6700	Approved
0.6404	Remote Similarity	NPD6701	Clinical (unspecified phase)
0.6351	Remote Similarity	NPD371	Approved
0.6333	Remote Similarity	NPD6702	Approved
0.6333	Remote Similarity	NPD6703	Approved
0.6292	Remote Similarity	NPD4753	Phase 2
0.6292	Remote Similarity	NPD5328	Approved
0.6279	Remote Similarity	NPD3133	Approved
0.6279	Remote Similarity	NPD4786	Approved
0.6279	Remote Similarity	NPD3665	Phase 1
0.6279	Remote Similarity	NPD3666	Approved
0.6235	Remote Similarity	NPD4223	Phase 3
0.6235	Remote Similarity	NPD4221	Approved
0.6207	Remote Similarity	NPD5329	Approved
0.619	Remote Similarity	NPD7509	Discontinued
0.619	Remote Similarity	NPD6930	Phase 2
0.619	Remote Similarity	NPD6931	Approved
0.617	Remote Similarity	NPD4755	Approved
0.6154	Remote Similarity	NPD8034	Phase 2
0.6154	Remote Similarity	NPD6923	Approved
0.6154	Remote Similarity	NPD6079	Approved
0.6154	Remote Similarity	NPD6922	Approved
0.6154	Remote Similarity	NPD8035	Phase 2
0.6146	Remote Similarity	NPD4159	Approved
0.6136	Remote Similarity	NPD3618	Phase 1
0.6129	Remote Similarity	NPD7991	Discontinued
0.6122	Remote Similarity	NPD8170	Clinical (unspecified phase)
0.6118	Remote Similarity	NPD4692	Approved
0.6118	Remote Similarity	NPD4139	Approved
0.6092	Remote Similarity	NPD4197	Approved
0.6076	Remote Similarity	NPD7144	Approved
0.6076	Remote Similarity	NPD7143	Approved
0.6071	Remote Similarity	NPD6929	Approved
0.6067	Remote Similarity	NPD7524	Approved
0.6049	Remote Similarity	NPD1810	Approved
0.6049	Remote Similarity	NPD1811	Approved
0.6047	Remote Similarity	NPD3667	Approved
0.6042	Remote Similarity	NPD5286	Approved
0.6042	Remote Similarity	NPD4700	Approved
0.6042	Remote Similarity	NPD5285	Approved
0.6042	Remote Similarity	NPD4696	Approved
0.6027	Remote Similarity	NPD3198	Approved
0.6024	Remote Similarity	NPD6932	Approved
0.6	Remote Similarity	NPD7150	Approved
0.6	Remote Similarity	NPD7919	Phase 3
0.6	Remote Similarity	NPD7920	Phase 3
0.6	Remote Similarity	NPD388	Approved
0.6	Remote Similarity	NPD6083	Phase 2
0.6	Remote Similarity	NPD7151	Approved
0.6	Remote Similarity	NPD7152	Approved
0.6	Remote Similarity	NPD386	Approved
0.6	Remote Similarity	NPD6084	Phase 2
0.5979	Remote Similarity	NPD5223	Approved
0.5977	Remote Similarity	NPD6695	Phase 3
0.5957	Remote Similarity	NPD5210	Approved
0.5957	Remote Similarity	NPD4629	Approved
0.5955	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.5955	Remote Similarity	NPD4688	Approved
0.5955	Remote Similarity	NPD4689	Approved
0.5955	Remote Similarity	NPD5205	Approved
0.5955	Remote Similarity	NPD4690	Approved
0.5955	Remote Similarity	NPD4138	Approved
0.5955	Remote Similarity	NPD8308	Discontinued
0.5955	Remote Similarity	NPD4693	Phase 3
0.5938	Remote Similarity	NPD8088	Phase 1
0.5938	Remote Similarity	NPD7638	Approved
0.5918	Remote Similarity	NPD5226	Approved
0.5918	Remote Similarity	NPD4633	Approved
0.5918	Remote Similarity	NPD5211	Phase 2
0.5918	Remote Similarity	NPD5225	Approved
0.5918	Remote Similarity	NPD5224	Approved
0.5909	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.59	Remote Similarity	NPD7128	Approved
0.59	Remote Similarity	NPD5739	Approved
0.59	Remote Similarity	NPD6402	Approved
0.59	Remote Similarity	NPD6675	Approved
0.5882	Remote Similarity	NPD6683	Phase 2
0.5876	Remote Similarity	NPD7639	Approved
0.5876	Remote Similarity	NPD8418	Phase 2
0.5876	Remote Similarity	NPD7640	Approved
0.5859	Remote Similarity	NPD5174	Approved
0.5859	Remote Similarity	NPD4754	Approved
0.5859	Remote Similarity	NPD5175	Approved
0.5843	Remote Similarity	NPD6893	Approved
0.5833	Remote Similarity	NPD5776	Phase 2
0.5833	Remote Similarity	NPD6925	Approved
0.5825	Remote Similarity	NPD4634	Approved
0.5824	Remote Similarity	NPD4723	Approved
0.5824	Remote Similarity	NPD4722	Approved
0.5814	Remote Similarity	NPD7514	Phase 3
0.58	Remote Similarity	NPD5141	Approved
0.5784	Remote Similarity	NPD7320	Approved
0.5784	Remote Similarity	NPD6881	Approved
0.5784	Remote Similarity	NPD6899	Approved
0.5778	Remote Similarity	NPD5280	Approved
0.5778	Remote Similarity	NPD5690	Phase 2
0.5778	Remote Similarity	NPD4694	Approved
0.5765	Remote Similarity	NPD7145	Approved
0.5765	Remote Similarity	NPD7322	Clinical (unspecified phase)
0.5765	Remote Similarity	NPD3617	Approved
0.5761	Remote Similarity	NPD6051	Approved
0.5758	Remote Similarity	NPD7632	Discontinued
0.5743	Remote Similarity	NPD4768	Approved
0.5743	Remote Similarity	NPD4767	Approved
0.5741	Remote Similarity	NPD7327	Approved
0.5741	Remote Similarity	NPD7328	Approved
0.5729	Remote Similarity	NPD4697	Phase 3
0.5729	Remote Similarity	NPD5221	Approved
0.5729	Remote Similarity	NPD5222	Approved
0.5729	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.5728	Remote Similarity	NPD6372	Approved
0.5728	Remote Similarity	NPD6373	Approved
0.5714	Remote Similarity	NPD7750	Discontinued
0.5714	Remote Similarity	NPD8297	Approved
0.5688	Remote Similarity	NPD7516	Approved
0.5686	Remote Similarity	NPD5701	Approved
0.5686	Remote Similarity	NPD5697	Approved
0.5679	Remote Similarity	NPD2686	Approved
0.5679	Remote Similarity	NPD2687	Approved
0.5679	Remote Similarity	NPD2254	Approved
0.5673	Remote Similarity	NPD6883	Approved
0.5673	Remote Similarity	NPD7102	Approved
0.5673	Remote Similarity	NPD7290	Approved
0.567	Remote Similarity	NPD5173	Approved
0.566	Remote Similarity	NPD4632	Approved
0.5652	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.5638	Remote Similarity	NPD7515	Phase 2
0.5636	Remote Similarity	NPD8377	Approved
0.5636	Remote Similarity	NPD8294	Approved
0.5632	Remote Similarity	NPD7332	Phase 2
0.5631	Remote Similarity	NPD6011	Approved
0.5631	Remote Similarity	NPD4729	Approved
0.5631	Remote Similarity	NPD4730	Approved
0.5631	Remote Similarity	NPD5128	Approved
0.5625	Remote Similarity	NPD5695	Phase 3
0.5625	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.5619	Remote Similarity	NPD8130	Phase 1
0.5619	Remote Similarity	NPD6650	Approved
0.5619	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.5619	Remote Similarity	NPD6869	Approved
0.5619	Remote Similarity	NPD6847	Approved
0.5619	Remote Similarity	NPD6617	Approved
0.5619	Remote Similarity	NPD6649	Approved
0.5616	Remote Similarity	NPD586	Phase 1
0.5612	Remote Similarity	NPD5696	Approved
0.5604	Remote Similarity	NPD5330	Approved
0.5604	Remote Similarity	NPD7146	Approved
0.5604	Remote Similarity	NPD7521	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