NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	240.14
Volume:	246.179
LogP:	0.501
LogD:	0.287
LogS:	-2.01
# Rotatable Bonds:	2
TPSA:	66.76
# H-Bond Aceptor:	4
# H-Bond Donor:	2
# Rings:	2
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.701
Synthetic Accessibility Score:	5.496
Fsp3:	0.769
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:	-5.211
MDCK Permeability:	2.611231138871517e-05
Pgp-inhibitor:	0.003
Pgp-substrate:	0.255
Human Intestinal Absorption (HIA):	0.013
20% Bioavailability (F20%):	0.077
30% Bioavailability (F30%):	0.108

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.903
Plasma Protein Binding (PPB):	59.93781661987305%
Volume Distribution (VD):	0.608
Pgp-substrate:	59.3406867980957%

ADMET: Metabolism

CYP1A2-inhibitor:	0.007
CYP1A2-substrate:	0.968
CYP2C19-inhibitor:	0.021
CYP2C19-substrate:	0.819
CYP2C9-inhibitor:	0.017
CYP2C9-substrate:	0.056
CYP2D6-inhibitor:	0.002
CYP2D6-substrate:	0.051
CYP3A4-inhibitor:	0.116
CYP3A4-substrate:	0.88

ADMET: Excretion

Clearance (CL):	3.747
Half-life (T1/2):	0.421

ADMET: Toxicity

hERG Blockers:	0.021
Human Hepatotoxicity (H-HT):	0.591
Drug-inuced Liver Injury (DILI):	0.137
AMES Toxicity:	0.013
Rat Oral Acute Toxicity:	0.599
Maximum Recommended Daily Dose:	0.962
Skin Sensitization:	0.261
Carcinogencity:	0.93
Eye Corrosion:	0.004
Eye Irritation:	0.115
Respiratory Toxicity:	0.983

Download Data

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

Natural Product: NPC230623

Natural Product ID:	NPC230623
*Common Name:**	Drummondol
IUPAC Name:	(1S,5S,8S)-8-hydroxy-8-[(E)-3-hydroxybut-1-enyl]-1,5-dimethyl-6-oxabicyclo[3.2.1]octan-3-one
Synonyms:	Drummondol
Standard InCHIKey:	KENVUEOHDFOVNA-HQZIRTJDSA-N
Standard InCHI:	InChI=1S/C13H20O4/c1-9(14)4-5-13(16)11(2)6-10(15)7-12(13,3)17-8-11/h4-5,9,14,16H,6-8H2,1-3H3/b5-4+/t9?,11-,12-,13-/m0/s1
SMILES:	CC(/C=C/[C@@]1([C@@]2(C)CC(=O)C[C@]1(C)OC2)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL454176
PubChem CID:	44559359
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0001729] Oxepanes

*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
NPO16501	Capsicum annuum	Species	Solanaceae	Eukaryota	n.a.	fruit	n.a.	PMID[12932131]
NPO16501	Capsicum annuum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20460582]
NPO16501	Capsicum annuum	Species	Solanaceae	Eukaryota	n.a.	fruit	n.a.	PMID[25172746]
NPO16501	Capsicum annuum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[8910532]
NPO16501	Capsicum annuum	Species	Solanaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO16501	Capsicum annuum	Species	Solanaceae	Eukaryota	Fruit	n.a.	n.a.	Database[FooDB]
NPO16501	Capsicum annuum	Species	Solanaceae	Eukaryota	Leaf	n.a.	n.a.	Database[FooDB]
NPO16501	Capsicum annuum	Species	Solanaceae	Eukaryota	Pericarp	n.a.	n.a.	Database[FooDB]
NPO16501	Capsicum annuum	Species	Solanaceae	Eukaryota	Resin, Exudate, Sap	n.a.	n.a.	Database[FooDB]
NPO16501	Capsicum annuum	Species	Solanaceae	Eukaryota	Root	n.a.	n.a.	Database[FooDB]
NPO16501	Capsicum annuum	Species	Solanaceae	Eukaryota	Seed	n.a.	n.a.	Database[FooDB]
NPO16501	Capsicum annuum	Species	Solanaceae	Eukaryota	Tissue Culture	n.a.	n.a.	Database[FooDB]
NPO16501	Capsicum annuum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO16501	Capsicum annuum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO16501	Capsicum annuum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO16501	Capsicum annuum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO16501	Capsicum annuum	Species	Solanaceae	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
ED50	1

Activity Type	# Activity
Cell Line	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT91	Cell Line	KB	Homo sapiens	ED50	=	5.4	10'1 ug/ml	PMID[547462]

☑ 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 NPC230623 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	165
0.1-0.2	1051
0.2-0.3	4229
0.3-0.4	8266
0.4-0.5	14847
0.5-0.6	8009
0.6-0.7	5421
0.7-0.8	704
0.8-0.85	3
0.85-0.9	1
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.8925	High Similarity	NPC278008
0.8416	Intermediate Similarity	NPC46407
0.828	Intermediate Similarity	NPC475441
0.8172	Intermediate Similarity	NPC15059
0.7979	Intermediate Similarity	NPC230332
0.7925	Intermediate Similarity	NPC117712
0.7778	Intermediate Similarity	NPC27999
0.7778	Intermediate Similarity	NPC159763
0.7778	Intermediate Similarity	NPC477116
0.7778	Intermediate Similarity	NPC124512
0.7778	Intermediate Similarity	NPC278386
0.7767	Intermediate Similarity	NPC230541
0.7745	Intermediate Similarity	NPC258532
0.7732	Intermediate Similarity	NPC196227
0.7708	Intermediate Similarity	NPC116726
0.7708	Intermediate Similarity	NPC252433
0.7685	Intermediate Similarity	NPC179626
0.7685	Intermediate Similarity	NPC270929
0.7677	Intermediate Similarity	NPC134454
0.7677	Intermediate Similarity	NPC17326
0.7677	Intermediate Similarity	NPC474977
0.7667	Intermediate Similarity	NPC157895
0.7667	Intermediate Similarity	NPC148685
0.7667	Intermediate Similarity	NPC104120
0.766	Intermediate Similarity	NPC472324
0.7653	Intermediate Similarity	NPC316215
0.7634	Intermediate Similarity	NPC79573
0.7634	Intermediate Similarity	NPC52628
0.7624	Intermediate Similarity	NPC476897
0.7619	Intermediate Similarity	NPC141350
0.7615	Intermediate Similarity	NPC470775
0.7615	Intermediate Similarity	NPC469684
0.7615	Intermediate Similarity	NPC176513
0.7609	Intermediate Similarity	NPC251475
0.7609	Intermediate Similarity	NPC169941
0.7604	Intermediate Similarity	NPC472325
0.7604	Intermediate Similarity	NPC134321
0.7604	Intermediate Similarity	NPC214844
0.7596	Intermediate Similarity	NPC473284
0.7579	Intermediate Similarity	NPC87189
0.7579	Intermediate Similarity	NPC228415
0.7576	Intermediate Similarity	NPC11396
0.7576	Intermediate Similarity	NPC472734
0.7576	Intermediate Similarity	NPC472733
0.7576	Intermediate Similarity	NPC21302
0.7573	Intermediate Similarity	NPC296950
0.7573	Intermediate Similarity	NPC160843
0.757	Intermediate Similarity	NPC207251
0.757	Intermediate Similarity	NPC472002
0.7568	Intermediate Similarity	NPC475003
0.7553	Intermediate Similarity	NPC198761
0.7551	Intermediate Similarity	NPC472976
0.7551	Intermediate Similarity	NPC472977
0.7547	Intermediate Similarity	NPC5103
0.7545	Intermediate Similarity	NPC329736
0.7545	Intermediate Similarity	NPC470776
0.75	Intermediate Similarity	NPC472732
0.75	Intermediate Similarity	NPC166607
0.75	Intermediate Similarity	NPC120446
0.75	Intermediate Similarity	NPC471332
0.75	Intermediate Similarity	NPC473100
0.75	Intermediate Similarity	NPC474343
0.75	Intermediate Similarity	NPC236176
0.75	Intermediate Similarity	NPC472731
0.75	Intermediate Similarity	NPC73911
0.75	Intermediate Similarity	NPC27105
0.75	Intermediate Similarity	NPC471333
0.75	Intermediate Similarity	NPC474938
0.75	Intermediate Similarity	NPC474785
0.7477	Intermediate Similarity	NPC474229
0.7477	Intermediate Similarity	NPC188738
0.7477	Intermediate Similarity	NPC61520
0.7477	Intermediate Similarity	NPC470186
0.7476	Intermediate Similarity	NPC475050
0.7476	Intermediate Similarity	NPC473624
0.7475	Intermediate Similarity	NPC272617
0.7475	Intermediate Similarity	NPC134067
0.7474	Intermediate Similarity	NPC23622
0.7473	Intermediate Similarity	NPC236707
0.7453	Intermediate Similarity	NPC87335
0.7453	Intermediate Similarity	NPC143706
0.7453	Intermediate Similarity	NPC42662
0.7453	Intermediate Similarity	NPC472534
0.7453	Intermediate Similarity	NPC475065
0.7453	Intermediate Similarity	NPC214644
0.7447	Intermediate Similarity	NPC476602
0.7431	Intermediate Similarity	NPC326542
0.7431	Intermediate Similarity	NPC147912
0.7431	Intermediate Similarity	NPC67259
0.7429	Intermediate Similarity	NPC330011
0.7429	Intermediate Similarity	NPC112780
0.7429	Intermediate Similarity	NPC473165
0.7429	Intermediate Similarity	NPC329048
0.7429	Intermediate Similarity	NPC301666
0.7426	Intermediate Similarity	NPC153776
0.7426	Intermediate Similarity	NPC471330
0.7426	Intermediate Similarity	NPC316598
0.7426	Intermediate Similarity	NPC472730
0.7426	Intermediate Similarity	NPC472729
0.7426	Intermediate Similarity	NPC177680
0.7426	Intermediate Similarity	NPC212465
0.7426	Intermediate Similarity	NPC472687
0.7426	Intermediate Similarity	NPC99657
0.7426	Intermediate Similarity	NPC471331
0.7426	Intermediate Similarity	NPC177232
0.7426	Intermediate Similarity	NPC203388
0.7423	Intermediate Similarity	NPC473099
0.7423	Intermediate Similarity	NPC128672
0.7419	Intermediate Similarity	NPC105173
0.7416	Intermediate Similarity	NPC474197
0.7407	Intermediate Similarity	NPC269530
0.7404	Intermediate Similarity	NPC146731
0.7404	Intermediate Similarity	NPC75531
0.7404	Intermediate Similarity	NPC149124
0.74	Intermediate Similarity	NPC135576
0.74	Intermediate Similarity	NPC93271
0.7391	Intermediate Similarity	NPC471270
0.7391	Intermediate Similarity	NPC225049
0.7387	Intermediate Similarity	NPC284707
0.7387	Intermediate Similarity	NPC251310
0.7379	Intermediate Similarity	NPC477915
0.7374	Intermediate Similarity	NPC477241
0.7368	Intermediate Similarity	NPC476043
0.7368	Intermediate Similarity	NPC262026
0.7364	Intermediate Similarity	NPC207217
0.7364	Intermediate Similarity	NPC64318
0.7364	Intermediate Similarity	NPC474734
0.7358	Intermediate Similarity	NPC473482
0.7358	Intermediate Similarity	NPC475418
0.7358	Intermediate Similarity	NPC318363
0.7358	Intermediate Similarity	NPC94377
0.7356	Intermediate Similarity	NPC471268
0.7356	Intermediate Similarity	NPC471271
0.7353	Intermediate Similarity	NPC477521
0.7353	Intermediate Similarity	NPC472727
0.7353	Intermediate Similarity	NPC198880
0.7353	Intermediate Similarity	NPC306856
0.7353	Intermediate Similarity	NPC472728
0.7353	Intermediate Similarity	NPC477655
0.7347	Intermediate Similarity	NPC300312
0.7347	Intermediate Similarity	NPC476705
0.7347	Intermediate Similarity	NPC261607
0.7347	Intermediate Similarity	NPC472978
0.7347	Intermediate Similarity	NPC111114
0.734	Intermediate Similarity	NPC40687
0.734	Intermediate Similarity	NPC295799
0.7339	Intermediate Similarity	NPC317210
0.7339	Intermediate Similarity	NPC469463
0.7339	Intermediate Similarity	NPC469454
0.7339	Intermediate Similarity	NPC469496
0.7333	Intermediate Similarity	NPC149047
0.7333	Intermediate Similarity	NPC477125
0.7333	Intermediate Similarity	NPC85529
0.7333	Intermediate Similarity	NPC32006
0.7333	Intermediate Similarity	NPC102352
0.7327	Intermediate Similarity	NPC254496
0.7327	Intermediate Similarity	NPC239895
0.7321	Intermediate Similarity	NPC268958
0.732	Intermediate Similarity	NPC253618
0.732	Intermediate Similarity	NPC77001
0.7315	Intermediate Similarity	NPC304180
0.7315	Intermediate Similarity	NPC179798
0.7315	Intermediate Similarity	NPC157476
0.7315	Intermediate Similarity	NPC471243
0.7308	Intermediate Similarity	NPC194323
0.7308	Intermediate Similarity	NPC264048
0.7308	Intermediate Similarity	NPC168575
0.7308	Intermediate Similarity	NPC474165
0.7308	Intermediate Similarity	NPC90177
0.7308	Intermediate Similarity	NPC69171
0.7308	Intermediate Similarity	NPC471005
0.7304	Intermediate Similarity	NPC81736
0.7304	Intermediate Similarity	NPC172154
0.7304	Intermediate Similarity	NPC8369
0.73	Intermediate Similarity	NPC473170
0.73	Intermediate Similarity	NPC472469
0.73	Intermediate Similarity	NPC53565
0.7297	Intermediate Similarity	NPC286528
0.7297	Intermediate Similarity	NPC20302
0.7297	Intermediate Similarity	NPC97908
0.7297	Intermediate Similarity	NPC312824
0.7297	Intermediate Similarity	NPC471854
0.7297	Intermediate Similarity	NPC470959
0.7297	Intermediate Similarity	NPC474654
0.7297	Intermediate Similarity	NPC122033
0.7297	Intermediate Similarity	NPC470492
0.7297	Intermediate Similarity	NPC53396
0.7297	Intermediate Similarity	NPC476712
0.7297	Intermediate Similarity	NPC287343
0.7297	Intermediate Similarity	NPC167606
0.7297	Intermediate Similarity	NPC476965
0.7297	Intermediate Similarity	NPC470854
0.7297	Intermediate Similarity	NPC470493
0.7297	Intermediate Similarity	NPC140055
0.7297	Intermediate Similarity	NPC183580
0.7297	Intermediate Similarity	NPC476713
0.7297	Intermediate Similarity	NPC218970
0.7297	Intermediate Similarity	NPC58662
0.7297	Intermediate Similarity	NPC98249
0.7292	Intermediate Similarity	NPC179659

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 NPC230623 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	146
0.1-0.2	1455
0.2-0.3	3874
0.3-0.4	2454
0.4-0.5	765
0.5-0.6	274
0.6-0.7	178
0.7-0.8	4
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
0.7778	Intermediate Similarity	NPD4225	Approved
0.7297	Intermediate Similarity	NPD7115	Discovery
0.7129	Intermediate Similarity	NPD1698	Clinical (unspecified phase)
0.71	Intermediate Similarity	NPD5779	Approved
0.71	Intermediate Similarity	NPD5778	Approved
0.7037	Intermediate Similarity	NPD5345	Clinical (unspecified phase)
0.701	Intermediate Similarity	NPD5786	Approved
0.7	Intermediate Similarity	NPD6411	Approved
0.6887	Remote Similarity	NPD5211	Phase 2
0.6863	Remote Similarity	NPD5282	Discontinued
0.6832	Remote Similarity	NPD7983	Approved
0.68	Remote Similarity	NPD6101	Approved
0.68	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6771	Remote Similarity	NPD4270	Approved
0.6771	Remote Similarity	NPD4269	Approved
0.6768	Remote Similarity	NPD7524	Approved
0.6759	Remote Similarity	NPD5141	Approved
0.6757	Remote Similarity	NPD4634	Approved
0.6733	Remote Similarity	NPD5785	Approved
0.6698	Remote Similarity	NPD5285	Approved
0.6698	Remote Similarity	NPD5286	Approved
0.6698	Remote Similarity	NPD4696	Approved
0.6667	Remote Similarity	NPD5369	Approved
0.6667	Remote Similarity	NPD6054	Approved
0.6667	Remote Similarity	NPD3618	Phase 1
0.6667	Remote Similarity	NPD7637	Suspended
0.6667	Remote Similarity	NPD6319	Approved
0.6667	Remote Similarity	NPD4755	Approved
0.6667	Remote Similarity	NPD6079	Approved
0.6637	Remote Similarity	NPD8297	Approved
0.6636	Remote Similarity	NPD5697	Approved
0.6634	Remote Similarity	NPD5328	Approved
0.661	Remote Similarity	NPD6015	Approved
0.661	Remote Similarity	NPD6016	Approved
0.6607	Remote Similarity	NPD6371	Approved
0.6598	Remote Similarity	NPD3667	Approved
0.6577	Remote Similarity	NPD6899	Approved
0.6577	Remote Similarity	NPD6881	Approved
0.6574	Remote Similarity	NPD4633	Approved
0.6574	Remote Similarity	NPD5225	Approved
0.6574	Remote Similarity	NPD5226	Approved
0.6574	Remote Similarity	NPD5224	Approved
0.6571	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6571	Remote Similarity	NPD4697	Phase 3
0.6571	Remote Similarity	NPD5221	Approved
0.6571	Remote Similarity	NPD5222	Approved
0.6566	Remote Similarity	NPD1696	Phase 3
0.6566	Remote Similarity	NPD5363	Approved
0.6566	Remote Similarity	NPD1694	Approved
0.6562	Remote Similarity	NPD4252	Approved
0.6555	Remote Similarity	NPD5988	Approved
0.6555	Remote Similarity	NPD6370	Approved
0.6549	Remote Similarity	NPD6650	Approved
0.6549	Remote Similarity	NPD6649	Approved
0.6545	Remote Similarity	NPD6402	Approved
0.6545	Remote Similarity	NPD6675	Approved
0.6545	Remote Similarity	NPD5739	Approved
0.6545	Remote Similarity	NPD7128	Approved
0.6542	Remote Similarity	NPD4700	Approved
0.6526	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6525	Remote Similarity	NPD6059	Approved
0.6518	Remote Similarity	NPD6373	Approved
0.6518	Remote Similarity	NPD6014	Approved
0.6518	Remote Similarity	NPD6013	Approved
0.6518	Remote Similarity	NPD6372	Approved
0.6518	Remote Similarity	NPD6012	Approved
0.6514	Remote Similarity	NPD5174	Approved
0.6514	Remote Similarity	NPD5175	Approved
0.6509	Remote Similarity	NPD5173	Approved
0.65	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6486	Remote Similarity	NPD5701	Approved
0.6481	Remote Similarity	NPD5344	Discontinued
0.6481	Remote Similarity	NPD5223	Approved
0.6471	Remote Similarity	NPD8517	Approved
0.6471	Remote Similarity	NPD8513	Phase 3
0.6471	Remote Similarity	NPD8516	Approved
0.6471	Remote Similarity	NPD8515	Approved
0.6465	Remote Similarity	NPD4786	Approved
0.646	Remote Similarity	NPD7290	Approved
0.646	Remote Similarity	NPD7102	Approved
0.646	Remote Similarity	NPD6883	Approved
0.6446	Remote Similarity	NPD7492	Approved
0.6442	Remote Similarity	NPD6399	Phase 3
0.6435	Remote Similarity	NPD4632	Approved
0.6429	Remote Similarity	NPD7320	Approved
0.6429	Remote Similarity	NPD6435	Approved
0.6429	Remote Similarity	NPD6011	Approved
0.6404	Remote Similarity	NPD6617	Approved
0.6404	Remote Similarity	NPD8130	Phase 1
0.6404	Remote Similarity	NPD6847	Approved
0.6404	Remote Similarity	NPD6869	Approved
0.6393	Remote Similarity	NPD6616	Approved
0.6392	Remote Similarity	NPD4822	Approved
0.6392	Remote Similarity	NPD4820	Approved
0.6392	Remote Similarity	NPD4819	Approved
0.6392	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6392	Remote Similarity	NPD4821	Approved
0.6389	Remote Similarity	NPD7640	Approved
0.6389	Remote Similarity	NPD7639	Approved
0.6372	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD7154	Phase 3
0.6364	Remote Similarity	NPD6695	Phase 3
0.6348	Remote Similarity	NPD6882	Approved
0.6346	Remote Similarity	NPD4810	Clinical (unspecified phase)
0.6341	Remote Similarity	NPD7078	Approved
0.6337	Remote Similarity	NPD4519	Discontinued
0.6337	Remote Similarity	NPD4623	Approved
0.6333	Remote Similarity	NPD6921	Approved
0.6321	Remote Similarity	NPD5210	Approved
0.6321	Remote Similarity	NPD4629	Approved
0.6311	Remote Similarity	NPD4753	Phase 2
0.63	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.63	Remote Similarity	NPD3666	Approved
0.63	Remote Similarity	NPD3665	Phase 1
0.63	Remote Similarity	NPD3133	Approved
0.6296	Remote Similarity	NPD7638	Approved
0.629	Remote Similarity	NPD7736	Approved
0.6286	Remote Similarity	NPD4202	Approved
0.6283	Remote Similarity	NPD4730	Approved
0.6283	Remote Similarity	NPD4729	Approved
0.6283	Remote Similarity	NPD6686	Approved
0.6262	Remote Similarity	NPD7839	Suspended
0.625	Remote Similarity	NPD4767	Approved
0.625	Remote Similarity	NPD4768	Approved
0.625	Remote Similarity	NPD6008	Approved
0.624	Remote Similarity	NPD7319	Approved
0.623	Remote Similarity	NPD8328	Phase 3
0.6226	Remote Similarity	NPD7748	Approved
0.6224	Remote Similarity	NPD5368	Approved
0.6216	Remote Similarity	NPD4754	Approved
0.621	Remote Similarity	NPD8074	Phase 3
0.621	Remote Similarity	NPD8293	Discontinued
0.6204	Remote Similarity	NPD6083	Phase 2
0.6204	Remote Similarity	NPD7902	Approved
0.6204	Remote Similarity	NPD6084	Phase 2
0.62	Remote Similarity	NPD5362	Discontinued
0.62	Remote Similarity	NPD6110	Phase 1
0.6195	Remote Similarity	NPD6412	Phase 2
0.6195	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.619	Remote Similarity	NPD7515	Phase 2
0.6186	Remote Similarity	NPD4268	Approved
0.6186	Remote Similarity	NPD4271	Approved
0.6176	Remote Similarity	NPD4249	Approved
0.6176	Remote Similarity	NPD5279	Phase 3
0.6174	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6174	Remote Similarity	NPD5251	Approved
0.6174	Remote Similarity	NPD5249	Phase 3
0.6174	Remote Similarity	NPD5248	Approved
0.6174	Remote Similarity	NPD5250	Approved
0.6174	Remote Similarity	NPD5247	Approved
0.6168	Remote Similarity	NPD5695	Phase 3
0.6154	Remote Similarity	NPD5370	Suspended
0.6147	Remote Similarity	NPD5696	Approved
0.6146	Remote Similarity	NPD6933	Approved
0.614	Remote Similarity	NPD5128	Approved
0.6139	Remote Similarity	NPD3668	Phase 3
0.6134	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6134	Remote Similarity	NPD6009	Approved
0.6129	Remote Similarity	NPD7507	Approved
0.6121	Remote Similarity	NPD5216	Approved
0.6121	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6121	Remote Similarity	NPD5215	Approved
0.6121	Remote Similarity	NPD5217	Approved
0.6121	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6117	Remote Similarity	NPD4251	Approved
0.6117	Remote Similarity	NPD7750	Discontinued
0.6117	Remote Similarity	NPD4250	Approved
0.6117	Remote Similarity	NPD3573	Approved
0.61	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.61	Remote Similarity	NPD4800	Clinical (unspecified phase)
0.6095	Remote Similarity	NPD46	Approved
0.6095	Remote Similarity	NPD6698	Approved
0.6091	Remote Similarity	NPD6648	Approved
0.6087	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6078	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.6066	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.6066	Remote Similarity	NPD5983	Phase 2
0.6061	Remote Similarity	NPD7525	Registered
0.6061	Remote Similarity	NPD4695	Discontinued
0.6061	Remote Similarity	NPD7332	Phase 2
0.6061	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.6061	Remote Similarity	NPD6931	Approved
0.6061	Remote Similarity	NPD6930	Phase 2
0.6061	Remote Similarity	NPD7514	Phase 3
0.605	Remote Similarity	NPD6274	Approved
0.6042	Remote Similarity	NPD8264	Approved
0.6034	Remote Similarity	NPD5135	Approved
0.6034	Remote Similarity	NPD5169	Approved
0.6034	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.6033	Remote Similarity	NPD7100	Approved
0.6033	Remote Similarity	NPD7101	Approved
0.6032	Remote Similarity	NPD6033	Approved
0.602	Remote Similarity	NPD7322	Clinical (unspecified phase)
0.6019	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6	Remote Similarity	NPD6317	Approved
0.6	Remote Similarity	NPD5168	Approved
0.5983	Remote Similarity	NPD5127	Approved
0.5968	Remote Similarity	NPD7604	Phase 2
0.596	Remote Similarity	NPD7645	Phase 2
0.596	Remote Similarity	NPD6929	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