NPASS Compound

Structure

CID193741 OpenBabel06191715582D 29 32 0 0 1 0 0 0 0 0999 V2000 6.9282 -2.0000 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 3.4641 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 1.9563 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 -0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 4.3301 -0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.4641 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.0000 -2.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 5.0733 0.1691 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 4.6665 1.0827 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 5.1962 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8660 -0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.6720 0.9781 0.0000 C 0 0 1 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 4.2072 2.6254 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.7210 1.2872 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 -1.5000 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 0.0000 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.6611 0.9781 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 25 1 0 0 0 0 2 18 1 0 0 0 0 3 5 2 0 0 0 0 3 26 1 0 0 0 0 4 17 1 0 0 0 0 4 19 1 0 0 0 0 5 14 1 0 0 0 0 6 2 1 1 0 0 0 6 9 1 0 0 0 0 6 27 1 0 0 0 0 7 5 1 6 0 0 0 7 8 1 0 0 0 0 7 12 1 0 0 0 0 8 15 1 0 0 0 0 8 17 1 6 0 0 0 9 10 1 0 0 0 0 9 20 1 6 0 0 0 10 11 1 0 0 0 0 10 21 1 1 0 0 0 11 16 1 0 0 0 0 11 22 1 6 0 0 0 12 13 1 0 0 0 0 12 28 1 1 0 0 0 13 17 1 1 0 0 0 13 28 1 0 0 0 0 14 23 2 0 0 0 0 14 25 1 0 0 0 0 15 26 1 0 0 0 0 15 29 1 1 0 0 0 16 27 1 0 0 0 0 16 29 1 1 0 0 0 17 24 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	420.13
Volume:	368.572
LogP:	-0.649
LogD:	-0.488
LogS:	-1.129
# Rotatable Bonds:	6
TPSA:	187.9
# H-Bond Aceptor:	12
# H-Bond Donor:	6
# Rings:	4
# Heavy Atoms:	12

MedChem Properties

QED Drug-Likeness Score:	0.187
Synthetic Accessibility Score:	5.112
Fsp3:	0.824
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-6.207
MDCK Permeability:	0.00014920193643774837
Pgp-inhibitor:	0.001
Pgp-substrate:	0.241
Human Intestinal Absorption (HIA):	0.6
20% Bioavailability (F20%):	0.011
30% Bioavailability (F30%):	0.996

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.191
Plasma Protein Binding (PPB):	20.214147567749023%
Volume Distribution (VD):	0.342
Pgp-substrate:	55.28323745727539%

ADMET: Metabolism

CYP1A2-inhibitor:	0.014
CYP1A2-substrate:	0.172
CYP2C19-inhibitor:	0.013
CYP2C19-substrate:	0.068
CYP2C9-inhibitor:	0.002
CYP2C9-substrate:	0.029
CYP2D6-inhibitor:	0.005
CYP2D6-substrate:	0.098
CYP3A4-inhibitor:	0.008
CYP3A4-substrate:	0.045

ADMET: Excretion

Clearance (CL):	1.312
Half-life (T1/2):	0.836

ADMET: Toxicity

hERG Blockers:	0.053
Human Hepatotoxicity (H-HT):	0.299
Drug-inuced Liver Injury (DILI):	0.754
AMES Toxicity:	0.088
Rat Oral Acute Toxicity:	0.016
Maximum Recommended Daily Dose:	0.004
Skin Sensitization:	0.107
Carcinogencity:	0.771
Eye Corrosion:	0.003
Eye Irritation:	0.115
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: NPC193741

Natural Product ID:	NPC193741
*Common Name:**	6Beta,7Beta-Epoxy-8-Epi-Splendoside
IUPAC Name:	methyl (1aS,1bS,5S,5aS,6S,6aS)-6-hydroxy-6-(hydroxymethyl)-5-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-1b,5,5a,6a-tetrahydro-1aH-oxireno[3,4]cyclopenta[1,3-d]pyran-2-carboxylate
Synonyms:
Standard InCHIKey:	ZHTGZWDWDCHEOX-HWCJXECGSA-N
Standard InCHI:	InChI=1S/C17H24O12/c1-25-14(23)5-3-26-15(8-7(5)12-13(28-12)17(8,24)4-19)29-16-11(22)10(21)9(20)6(2-18)27-16/h3,6-13,15-16,18-22,24H,2,4H2,1H3/t6-,7-,8-,9-,10+,11-,12+,13+,15+,16+,17-/m1/s1
SMILES:	COC(=O)C1=CO[C@H]([C@H]2[C@@H]1[C@H]1[C@@H]([C@]2(CO)O)O1)O[C@H]1[C@@H]([C@H]([C@@H]([C@@H](CO)O1)O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL514583
PubChem CID:	11166049
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0004603] Organic oxygen compounds [CHEMONTID:0000323] Organooxygen compounds [CHEMONTID:0000011] Carbohydrates and carbohydrate conjugates [CHEMONTID:0002105] Glycosyl compounds [CHEMONTID:0002207] O-glycosyl compounds

*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
NPO4323	Morinda citrifolia	Species	Rubiaceae	Eukaryota	n.a.	leaf	n.a.	PMID[11348221]
NPO4323	Morinda citrifolia	Species	Rubiaceae	Eukaryota	fruit	n.a.	n.a.	PMID[15844957]
NPO4323	Morinda citrifolia	Species	Rubiaceae	Eukaryota	fruits	n.a.	n.a.	PMID[16378361]
NPO4323	Morinda citrifolia	Species	Rubiaceae	Eukaryota	fruits	Tahiti	n.a.	PMID[17378609]
NPO4323	Morinda citrifolia	Species	Rubiaceae	Eukaryota	Fruits	n.a.	n.a.	PMID[17480098]
NPO4323	Morinda citrifolia	Species	Rubiaceae	Eukaryota	roots	n.a.	n.a.	PMID[18076142]
NPO4323	Morinda citrifolia	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24224843]
NPO4323	Morinda citrifolia	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[27196335]
NPO4323	Morinda citrifolia	Species	Rubiaceae	Eukaryota	Fruits	n.a.	n.a.	PMID[32083868]
NPO4323	Morinda citrifolia	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO4323	Morinda citrifolia	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO4323	Morinda citrifolia	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO4323	Morinda citrifolia	Species	Rubiaceae	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	3

Activity Type	# Activity
NON-MOLECULAR	2
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1	Others	Radical scavenging activity		IC50	>	30000.0	nM	PMID[528400]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	>	30000.0	nM	PMID[528400]

☑ 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 NPC193741 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	256
0.1-0.2	1721
0.2-0.3	5831
0.3-0.4	11098
0.4-0.5	11389
0.5-0.6	7636
0.6-0.7	4214
0.7-0.8	504
0.8-0.85	27
0.85-0.9	6
0.9-0.95	9
0.95-1	6

Similarity Score	Similarity Level	Natural Product ID
0.9806	High Similarity	NPC475851
0.9806	High Similarity	NPC475924
0.9703	High Similarity	NPC80338
0.9703	High Similarity	NPC197813
0.9703	High Similarity	NPC148270
0.9604	High Similarity	NPC170432
0.9412	High Similarity	NPC127235
0.9406	High Similarity	NPC37240
0.9406	High Similarity	NPC475928
0.9307	High Similarity	NPC474730
0.9307	High Similarity	NPC4899
0.9307	High Similarity	NPC177013
0.9307	High Similarity	NPC35185
0.9231	High Similarity	NPC110701
0.902	High Similarity	NPC287539
0.902	High Similarity	NPC3488
0.8932	High Similarity	NPC106668
0.8846	High Similarity	NPC27687
0.8627	High Similarity	NPC284063
0.8627	High Similarity	NPC161293
0.8544	High Similarity	NPC86843
0.8529	High Similarity	NPC6765
0.8529	High Similarity	NPC93869
0.8491	Intermediate Similarity	NPC329834
0.8431	Intermediate Similarity	NPC274588
0.8396	Intermediate Similarity	NPC80144
0.8396	Intermediate Similarity	NPC304163
0.8381	Intermediate Similarity	NPC471381
0.8381	Intermediate Similarity	NPC186861
0.8302	Intermediate Similarity	NPC67296
0.8302	Intermediate Similarity	NPC216911
0.8302	Intermediate Similarity	NPC476228
0.8286	Intermediate Similarity	NPC37866
0.8286	Intermediate Similarity	NPC49833
0.8286	Intermediate Similarity	NPC249171
0.8269	Intermediate Similarity	NPC170527
0.8252	Intermediate Similarity	NPC63897
0.8235	Intermediate Similarity	NPC66504
0.8208	Intermediate Similarity	NPC476211
0.8208	Intermediate Similarity	NPC476320
0.819	Intermediate Similarity	NPC236580
0.819	Intermediate Similarity	NPC304445
0.819	Intermediate Similarity	NPC471150
0.8165	Intermediate Similarity	NPC54737
0.8148	Intermediate Similarity	NPC473148
0.8131	Intermediate Similarity	NPC27474
0.8131	Intermediate Similarity	NPC476230
0.8108	Intermediate Similarity	NPC59489
0.8108	Intermediate Similarity	NPC139838
0.8058	Intermediate Similarity	NPC235051
0.8036	Intermediate Similarity	NPC50223
0.8019	Intermediate Similarity	NPC58267
0.8019	Intermediate Similarity	NPC263674
0.8019	Intermediate Similarity	NPC261372
0.8	Intermediate Similarity	NPC41681
0.8	Intermediate Similarity	NPC472873
0.7982	Intermediate Similarity	NPC329704
0.7963	Intermediate Similarity	NPC298255
0.7963	Intermediate Similarity	NPC28304
0.7961	Intermediate Similarity	NPC120021
0.7961	Intermediate Similarity	NPC270908
0.7961	Intermediate Similarity	NPC470573
0.7961	Intermediate Similarity	NPC246173
0.7961	Intermediate Similarity	NPC231710
0.7961	Intermediate Similarity	NPC216826
0.7961	Intermediate Similarity	NPC65665
0.7944	Intermediate Similarity	NPC45125
0.7925	Intermediate Similarity	NPC474297
0.789	Intermediate Similarity	NPC261117
0.789	Intermediate Similarity	NPC195510
0.789	Intermediate Similarity	NPC310804
0.789	Intermediate Similarity	NPC13171
0.7885	Intermediate Similarity	NPC473150
0.7885	Intermediate Similarity	NPC294643
0.7885	Intermediate Similarity	NPC274274
0.7876	Intermediate Similarity	NPC41551
0.787	Intermediate Similarity	NPC255677
0.787	Intermediate Similarity	NPC22149
0.787	Intermediate Similarity	NPC306344
0.7864	Intermediate Similarity	NPC22918
0.7864	Intermediate Similarity	NPC50464
0.785	Intermediate Similarity	NPC472290
0.7845	Intermediate Similarity	NPC277583
0.7843	Intermediate Similarity	NPC31349
0.783	Intermediate Similarity	NPC476053
0.783	Intermediate Similarity	NPC167893
0.7815	Intermediate Similarity	NPC473228
0.7815	Intermediate Similarity	NPC470829
0.7788	Intermediate Similarity	NPC117596
0.7767	Intermediate Similarity	NPC148534
0.7748	Intermediate Similarity	NPC86095
0.7745	Intermediate Similarity	NPC470657
0.7742	Intermediate Similarity	NPC213634
0.7736	Intermediate Similarity	NPC71589
0.7727	Intermediate Similarity	NPC222062
0.7727	Intermediate Similarity	NPC250545
0.7714	Intermediate Similarity	NPC472125
0.7714	Intermediate Similarity	NPC472126
0.7714	Intermediate Similarity	NPC472124
0.7714	Intermediate Similarity	NPC155215
0.7712	Intermediate Similarity	NPC13710
0.7706	Intermediate Similarity	NPC473146
0.7692	Intermediate Similarity	NPC93190
0.7692	Intermediate Similarity	NPC5153
0.7692	Intermediate Similarity	NPC170692
0.7692	Intermediate Similarity	NPC255450
0.7692	Intermediate Similarity	NPC48414
0.7679	Intermediate Similarity	NPC44004
0.767	Intermediate Similarity	NPC258501
0.7658	Intermediate Similarity	NPC284929
0.7658	Intermediate Similarity	NPC118761
0.7658	Intermediate Similarity	NPC234304
0.7658	Intermediate Similarity	NPC267869
0.7658	Intermediate Similarity	NPC197541
0.7642	Intermediate Similarity	NPC258216
0.7642	Intermediate Similarity	NPC212486
0.7642	Intermediate Similarity	NPC61201
0.7638	Intermediate Similarity	NPC158350
0.7632	Intermediate Similarity	NPC208307
0.7619	Intermediate Similarity	NPC307699
0.7619	Intermediate Similarity	NPC216284
0.7615	Intermediate Similarity	NPC472015
0.7607	Intermediate Similarity	NPC305044
0.7607	Intermediate Similarity	NPC265290
0.7593	Intermediate Similarity	NPC241911
0.7576	Intermediate Similarity	NPC471172
0.7568	Intermediate Similarity	NPC471599
0.7563	Intermediate Similarity	NPC475401
0.7547	Intermediate Similarity	NPC475881
0.7547	Intermediate Similarity	NPC470379
0.7547	Intermediate Similarity	NPC470373
0.7547	Intermediate Similarity	NPC70251
0.7547	Intermediate Similarity	NPC276298
0.7545	Intermediate Similarity	NPC244878
0.754	Intermediate Similarity	NPC155529
0.7524	Intermediate Similarity	NPC92974
0.7524	Intermediate Similarity	NPC215556
0.7524	Intermediate Similarity	NPC472872
0.7523	Intermediate Similarity	NPC181151
0.7522	Intermediate Similarity	NPC223450
0.7522	Intermediate Similarity	NPC243998
0.7521	Intermediate Similarity	NPC101400
0.7521	Intermediate Similarity	NPC101965
0.7521	Intermediate Similarity	NPC287075
0.7519	Intermediate Similarity	NPC48813
0.7519	Intermediate Similarity	NPC194854
0.75	Intermediate Similarity	NPC123505
0.75	Intermediate Similarity	NPC14961
0.75	Intermediate Similarity	NPC186148
0.75	Intermediate Similarity	NPC474750
0.75	Intermediate Similarity	NPC163228
0.75	Intermediate Similarity	NPC474783
0.75	Intermediate Similarity	NPC260809
0.75	Intermediate Similarity	NPC477092
0.75	Intermediate Similarity	NPC101051
0.75	Intermediate Similarity	NPC270013
0.7479	Intermediate Similarity	NPC475305
0.7478	Intermediate Similarity	NPC77089
0.7477	Intermediate Similarity	NPC473332
0.7477	Intermediate Similarity	NPC20673
0.7477	Intermediate Similarity	NPC471767
0.7477	Intermediate Similarity	NPC219038
0.7476	Intermediate Similarity	NPC149725
0.7476	Intermediate Similarity	NPC47958
0.7476	Intermediate Similarity	NPC304509
0.7463	Intermediate Similarity	NPC475462
0.7463	Intermediate Similarity	NPC16729
0.7462	Intermediate Similarity	NPC75616
0.746	Intermediate Similarity	NPC173347
0.7458	Intermediate Similarity	NPC121816
0.7456	Intermediate Similarity	NPC474285
0.7456	Intermediate Similarity	NPC254538
0.7455	Intermediate Similarity	NPC473307
0.7455	Intermediate Similarity	NPC151093
0.7453	Intermediate Similarity	NPC206614
0.7453	Intermediate Similarity	NPC474323
0.7438	Intermediate Similarity	NPC142882
0.7436	Intermediate Similarity	NPC313921
0.7436	Intermediate Similarity	NPC98038
0.7434	Intermediate Similarity	NPC169843
0.7431	Intermediate Similarity	NPC476009
0.7431	Intermediate Similarity	NPC306041
0.7431	Intermediate Similarity	NPC476315
0.7429	Intermediate Similarity	NPC58219
0.7429	Intermediate Similarity	NPC79549
0.7429	Intermediate Similarity	NPC177629
0.7422	Intermediate Similarity	NPC471234
0.7411	Intermediate Similarity	NPC475956
0.7411	Intermediate Similarity	NPC214714
0.7411	Intermediate Similarity	NPC200672
0.7411	Intermediate Similarity	NPC250594
0.7411	Intermediate Similarity	NPC252242
0.7407	Intermediate Similarity	NPC190294
0.7407	Intermediate Similarity	NPC81386
0.7407	Intermediate Similarity	NPC474035
0.7404	Intermediate Similarity	NPC470242
0.7404	Intermediate Similarity	NPC171484
0.7404	Intermediate Similarity	NPC149018
0.7402	Intermediate Similarity	NPC42206
0.7402	Intermediate Similarity	NPC471855

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 NPC193741 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	259
0.1-0.2	2263
0.2-0.3	3856
0.3-0.4	1860
0.4-0.5	537
0.5-0.6	275
0.6-0.7	98
0.7-0.8	2
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
0.7288	Intermediate Similarity	NPD6053	Discontinued
0.728	Intermediate Similarity	NPD7507	Approved
0.7241	Intermediate Similarity	NPD6686	Approved
0.7227	Intermediate Similarity	NPD8133	Approved
0.713	Intermediate Similarity	NPD46	Approved
0.713	Intermediate Similarity	NPD6698	Approved
0.7109	Intermediate Similarity	NPD7319	Approved
0.7097	Intermediate Similarity	NPD7503	Approved
0.696	Remote Similarity	NPD8513	Phase 3
0.6917	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6864	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6864	Remote Similarity	NPD6412	Phase 2
0.6833	Remote Similarity	NPD6371	Approved
0.6825	Remote Similarity	NPD8517	Approved
0.6825	Remote Similarity	NPD8516	Approved
0.6825	Remote Similarity	NPD8033	Approved
0.6825	Remote Similarity	NPD8515	Approved
0.6727	Remote Similarity	NPD1695	Approved
0.672	Remote Similarity	NPD7327	Approved
0.672	Remote Similarity	NPD7328	Approved
0.6696	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6695	Remote Similarity	NPD4057	Clinical (unspecified phase)
0.6695	Remote Similarity	NPD4056	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD7516	Approved
0.6667	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.6641	Remote Similarity	NPD7736	Approved
0.6641	Remote Similarity	NPD6370	Approved
0.6614	Remote Similarity	NPD8377	Approved
0.6614	Remote Similarity	NPD8294	Approved
0.6614	Remote Similarity	NPD6319	Approved
0.6589	Remote Similarity	NPD7642	Approved
0.6589	Remote Similarity	NPD7829	Approved
0.6589	Remote Similarity	NPD7830	Approved
0.6565	Remote Similarity	NPD8293	Discontinued
0.6562	Remote Similarity	NPD8380	Approved
0.6562	Remote Similarity	NPD8379	Approved
0.6562	Remote Similarity	NPD8296	Approved
0.6562	Remote Similarity	NPD8378	Approved
0.6562	Remote Similarity	NPD8335	Approved
0.6538	Remote Similarity	NPD7492	Approved
0.6518	Remote Similarity	NPD7838	Discovery
0.6508	Remote Similarity	NPD7115	Discovery
0.6508	Remote Similarity	NPD8137	Clinical (unspecified phase)
0.6508	Remote Similarity	NPD6009	Approved
0.6489	Remote Similarity	NPD6616	Approved
0.6484	Remote Similarity	NPD6054	Approved
0.6455	Remote Similarity	NPD4249	Approved
0.6452	Remote Similarity	NPD6882	Approved
0.6439	Remote Similarity	NPD7078	Approved
0.6434	Remote Similarity	NPD6015	Approved
0.6434	Remote Similarity	NPD6016	Approved
0.64	Remote Similarity	NPD4632	Approved
0.6396	Remote Similarity	NPD4250	Approved
0.6396	Remote Similarity	NPD4251	Approved
0.6389	Remote Similarity	NPD6435	Approved
0.6385	Remote Similarity	NPD8080	Discontinued
0.6385	Remote Similarity	NPD5988	Approved
0.6364	Remote Similarity	NPD6008	Approved
0.6364	Remote Similarity	NPD8451	Approved
0.6357	Remote Similarity	NPD6059	Approved
0.6328	Remote Similarity	NPD7641	Discontinued
0.632	Remote Similarity	NPD8297	Approved
0.6316	Remote Similarity	NPD8448	Approved
0.6316	Remote Similarity	NPD7983	Approved
0.6316	Remote Similarity	NPD8074	Phase 3
0.6308	Remote Similarity	NPD8274	Clinical (unspecified phase)
0.6281	Remote Similarity	NPD8170	Clinical (unspecified phase)
0.626	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.625	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.624	Remote Similarity	NPD6649	Approved
0.624	Remote Similarity	NPD6650	Approved
0.6212	Remote Similarity	NPD8328	Phase 3
0.621	Remote Similarity	NPD6373	Approved
0.621	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.621	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.621	Remote Similarity	NPD6372	Approved
0.6204	Remote Similarity	NPD5368	Approved
0.6182	Remote Similarity	NPD7154	Phase 3
0.6179	Remote Similarity	NPD5697	Approved
0.6176	Remote Similarity	NPD8390	Approved
0.6176	Remote Similarity	NPD8391	Approved
0.6176	Remote Similarity	NPD8392	Approved
0.6167	Remote Similarity	NPD5344	Discontinued
0.6165	Remote Similarity	NPD8340	Approved
0.6165	Remote Similarity	NPD8341	Approved
0.6165	Remote Similarity	NPD8299	Approved
0.6165	Remote Similarity	NPD8342	Approved
0.616	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6154	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6143	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.6129	Remote Similarity	NPD6881	Approved
0.6129	Remote Similarity	NPD6899	Approved
0.6098	Remote Similarity	NPD5739	Approved
0.6098	Remote Similarity	NPD6402	Approved
0.6098	Remote Similarity	NPD6675	Approved
0.6098	Remote Similarity	NPD7128	Approved
0.609	Remote Similarity	NPD7604	Phase 2
0.6087	Remote Similarity	NPD5785	Approved
0.608	Remote Similarity	NPD6014	Approved
0.608	Remote Similarity	NPD6012	Approved
0.608	Remote Similarity	NPD6013	Approved
0.6074	Remote Similarity	NPD7685	Pre-registration
0.6071	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6068	Remote Similarity	NPD5282	Discontinued
0.6061	Remote Similarity	NPD8267	Approved
0.6061	Remote Similarity	NPD8266	Approved
0.6061	Remote Similarity	NPD8444	Approved
0.6061	Remote Similarity	NPD5983	Phase 2
0.6061	Remote Similarity	NPD8269	Approved
0.6061	Remote Similarity	NPD8268	Approved
0.6055	Remote Similarity	NPD4820	Approved
0.6055	Remote Similarity	NPD4819	Approved
0.6055	Remote Similarity	NPD4821	Approved
0.6055	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6055	Remote Similarity	NPD4822	Approved
0.6048	Remote Similarity	NPD5701	Approved
0.6036	Remote Similarity	NPD5362	Discontinued
0.6032	Remote Similarity	NPD7102	Approved
0.6032	Remote Similarity	NPD6883	Approved
0.6032	Remote Similarity	NPD4634	Approved
0.6032	Remote Similarity	NPD7290	Approved
0.6018	Remote Similarity	NPD5786	Approved
0.6014	Remote Similarity	NPD7260	Phase 2
0.6	Remote Similarity	NPD7638	Approved
0.6	Remote Similarity	NPD6011	Approved
0.6	Remote Similarity	NPD5369	Approved
0.6	Remote Similarity	NPD7320	Approved
0.6	Remote Similarity	NPD4225	Approved
0.5984	Remote Similarity	NPD8083	Approved
0.5984	Remote Similarity	NPD8086	Approved
0.5984	Remote Similarity	NPD8084	Approved
0.5984	Remote Similarity	NPD6617	Approved
0.5984	Remote Similarity	NPD8138	Approved
0.5984	Remote Similarity	NPD8082	Approved
0.5984	Remote Similarity	NPD6847	Approved
0.5984	Remote Similarity	NPD8085	Approved
0.5984	Remote Similarity	NPD8139	Approved
0.5984	Remote Similarity	NPD8130	Phase 1
0.5984	Remote Similarity	NPD6869	Approved
0.5983	Remote Similarity	NPD5779	Approved
0.5983	Remote Similarity	NPD5778	Approved
0.5966	Remote Similarity	NPD7839	Suspended
0.595	Remote Similarity	NPD7639	Approved
0.595	Remote Similarity	NPD7640	Approved
0.5935	Remote Similarity	NPD8275	Approved
0.5935	Remote Similarity	NPD8276	Approved
0.5929	Remote Similarity	NPD5363	Approved
0.592	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.5917	Remote Similarity	NPD6084	Phase 2
0.5917	Remote Similarity	NPD6083	Phase 2
0.5912	Remote Similarity	NPD6033	Approved
0.5912	Remote Similarity	NPD8336	Approved
0.5912	Remote Similarity	NPD8337	Approved
0.5902	Remote Similarity	NPD1700	Approved
0.5893	Remote Similarity	NPD4788	Approved
0.5887	Remote Similarity	NPD8081	Approved
0.5882	Remote Similarity	NPD6336	Discontinued
0.5882	Remote Similarity	NPD5695	Phase 3
0.5872	Remote Similarity	NPD4802	Phase 2
0.5872	Remote Similarity	NPD4238	Approved
0.5872	Remote Similarity	NPD4268	Approved
0.5872	Remote Similarity	NPD4271	Approved
0.5868	Remote Similarity	NPD5696	Approved
0.5862	Remote Similarity	NPD6101	Approved
0.5862	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.5857	Remote Similarity	NPD6845	Suspended
0.5854	Remote Similarity	NPD5211	Phase 2
0.5852	Remote Similarity	NPD6067	Discontinued
0.5847	Remote Similarity	NPD6399	Phase 3
0.584	Remote Similarity	NPD8393	Approved
0.5827	Remote Similarity	NPD5956	Approved
0.5821	Remote Similarity	NPD6921	Approved
0.582	Remote Similarity	NPD4696	Approved
0.582	Remote Similarity	NPD5285	Approved
0.582	Remote Similarity	NPD6648	Approved
0.582	Remote Similarity	NPD5286	Approved
0.5804	Remote Similarity	NPD4269	Approved
0.5804	Remote Similarity	NPD4270	Approved
0.5802	Remote Similarity	NPD6274	Approved
0.5785	Remote Similarity	NPD4755	Approved
0.5763	Remote Similarity	NPD8034	Phase 2
0.5763	Remote Similarity	NPD6411	Approved
0.5763	Remote Similarity	NPD8035	Phase 2
0.576	Remote Similarity	NPD5141	Approved
0.5752	Remote Similarity	NPD3669	Approved
0.5752	Remote Similarity	NPD3670	Clinical (unspecified phase)
0.5745	Remote Similarity	NPD8338	Approved
0.5736	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.5726	Remote Similarity	NPD5225	Approved
0.5726	Remote Similarity	NPD5226	Approved
0.5726	Remote Similarity	NPD5224	Approved
0.5726	Remote Similarity	NPD4633	Approved
0.5714	Remote Similarity	NPD1780	Approved
0.5714	Remote Similarity	NPD1779	Approved
0.5702	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.5691	Remote Similarity	NPD4700	Approved
0.569	Remote Similarity	NPD7524	Approved
0.568	Remote Similarity	NPD5175	Approved
0.568	Remote Similarity	NPD5174	Approved
0.5672	Remote Similarity	NPD7100	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