NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	252.1
Volume:	243.777
LogP:	1.12
LogD:	0.938
LogS:	-3.143
# Rotatable Bonds:	0
TPSA:	83.83
# H-Bond Aceptor:	5
# H-Bond Donor:	2
# Rings:	3
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.59
Synthetic Accessibility Score:	5.74
Fsp3:	0.692
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:	-5.094
MDCK Permeability:	2.2120198991615325e-05
Pgp-inhibitor:	0.06
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.026
20% Bioavailability (F20%):	0.197
30% Bioavailability (F30%):	0.962

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.907
Plasma Protein Binding (PPB):	29.191017150878906%
Volume Distribution (VD):	0.8
Pgp-substrate:	66.82061004638672%

ADMET: Metabolism

CYP1A2-inhibitor:	0.034
CYP1A2-substrate:	0.918
CYP2C19-inhibitor:	0.031
CYP2C19-substrate:	0.829
CYP2C9-inhibitor:	0.017
CYP2C9-substrate:	0.049
CYP2D6-inhibitor:	0.003
CYP2D6-substrate:	0.109
CYP3A4-inhibitor:	0.062
CYP3A4-substrate:	0.476

ADMET: Excretion

Clearance (CL):	2.559
Half-life (T1/2):	0.311

ADMET: Toxicity

hERG Blockers:	0.018
Human Hepatotoxicity (H-HT):	0.49
Drug-inuced Liver Injury (DILI):	0.062
AMES Toxicity:	0.046
Rat Oral Acute Toxicity:	0.763
Maximum Recommended Daily Dose:	0.818
Skin Sensitization:	0.807
Carcinogencity:	0.654
Eye Corrosion:	0.013
Eye Irritation:	0.193
Respiratory Toxicity:	0.39

Download Data

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

Natural Product: NPC29827

Natural Product ID:	NPC29827
*Common Name:**	NPMJPMBCGOWCAJ-FYTYDNSOSA-N
IUPAC Name:	n.a.
Synonyms:	Rel-Acremostrictin
Standard InCHIKey:	NPMJPMBCGOWCAJ-FYTYDNSOSA-N
Standard InCHI:	InChI=1S/C13H16O5/c1-6-4-8-5-11(3)7(2)12(16,10(15)18-11)13(8,17)9(6)14/h4,7-8,16-17H,5H2,1-3H3/t7-,8+,11-,12-,13+/m0/s1
SMILES:	CC1=C[C@@H]2C[C@@]3(C)[C@H](C)[C@](C(=O)O3)([C@@]2(C1=O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1950958
PubChem CID:	56925681
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000050] Lactones [CHEMONTID:0001245] Gamma butyrolactones

*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
NPO8229	Sarocladium strictum	Species	n.a.	Eukaryota	n.a.	n.a.	n.a.	PMID[22136576]
NPO6006	Arundina graminifolia	Species	Orchidaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24063582]
NPO8229	Sarocladium strictum	Species	n.a.	Eukaryota	n.a.	n.a.	n.a.	PMID[7649852]
NPO14895	Eucalyptus wandoo	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO14895	Eucalyptus wandoo	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO14895	Eucalyptus wandoo	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO7343	Vernonia melleri	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16094	Stemphylium lycopersici	Species	Pleosporaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15104	Russula alutacea	Species	Russulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9654	Callitriche hamulata	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14999	Allium wallichii	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14895	Eucalyptus wandoo	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11850	Lonchocarpus sericeus	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12075	Guettarda angelica	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6006	Arundina graminifolia	Species	Orchidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8229	Sarocladium strictum	Species	n.a.	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	1
MIC	6

Activity Type	# Activity
Organism	6
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT729	Organism	Micrococcus luteus	Micrococcus luteus	MIC	=	50.0	ug.mL-1	PMID[476468]
NPT566	Organism	Salmonella typhimurium	Salmonella enterica subsp. enterica serovar Typhimurium	MIC	=	50.0	ug.mL-1	PMID[476468]
NPT766	Organism	Proteus vulgaris	Proteus vulgaris	MIC	=	12.5	ug.mL-1	PMID[476468]
NPT79	Organism	Bacillus subtilis	Bacillus subtilis	MIC	>	100.0	ug.mL-1	PMID[476468]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	>	100.0	ug.mL-1	PMID[476468]
NPT19	Organism	Escherichia coli	Escherichia coli	MIC	>	100.0	ug.mL-1	PMID[476468]
NPT1	Others	Radical scavenging activity		IC50	=	2100000.0	nM	PMID[476468]

☑ 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 NPC29827 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	233
0.1-0.2	1402
0.2-0.3	4968
0.3-0.4	8301
0.4-0.5	13901
0.5-0.6	8436
0.6-0.7	4641
0.7-0.8	798
0.8-0.85	15
0.85-0.9	1
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.8468	Intermediate Similarity	NPC207217
0.8407	Intermediate Similarity	NPC476107
0.8276	Intermediate Similarity	NPC473802
0.8261	Intermediate Similarity	NPC472401
0.823	Intermediate Similarity	NPC474654
0.823	Intermediate Similarity	NPC122033
0.823	Intermediate Similarity	NPC156252
0.823	Intermediate Similarity	NPC287343
0.823	Intermediate Similarity	NPC470854
0.823	Intermediate Similarity	NPC97908
0.8205	Intermediate Similarity	NPC473709
0.8205	Intermediate Similarity	NPC473919
0.819	Intermediate Similarity	NPC19464
0.8158	Intermediate Similarity	NPC106644
0.8136	Intermediate Similarity	NPC471939
0.8136	Intermediate Similarity	NPC217901
0.812	Intermediate Similarity	NPC472399
0.8099	Intermediate Similarity	NPC475139
0.8099	Intermediate Similarity	NPC180902
0.8067	Intermediate Similarity	NPC471940
0.8067	Intermediate Similarity	NPC168849
0.8067	Intermediate Similarity	NPC475273
0.8	Intermediate Similarity	NPC472397
0.8	Intermediate Similarity	NPC277017
0.8	Intermediate Similarity	NPC188667
0.8	Intermediate Similarity	NPC471125
0.8	Intermediate Similarity	NPC472758
0.8	Intermediate Similarity	NPC154608
0.8	Intermediate Similarity	NPC171905
0.8	Intermediate Similarity	NPC192813
0.8	Intermediate Similarity	NPC204552
0.8	Intermediate Similarity	NPC17772
0.7967	Intermediate Similarity	NPC475500
0.7967	Intermediate Similarity	NPC182266
0.7967	Intermediate Similarity	NPC100017
0.7967	Intermediate Similarity	NPC223356
0.7967	Intermediate Similarity	NPC473548
0.7967	Intermediate Similarity	NPC475154
0.7967	Intermediate Similarity	NPC471137
0.7967	Intermediate Similarity	NPC471136
0.7965	Intermediate Similarity	NPC49451
0.7965	Intermediate Similarity	NPC208998
0.7965	Intermediate Similarity	NPC7921
0.7949	Intermediate Similarity	NPC102822
0.7949	Intermediate Similarity	NPC477046
0.7946	Intermediate Similarity	NPC146945
0.7946	Intermediate Similarity	NPC171888
0.7934	Intermediate Similarity	NPC162495
0.7931	Intermediate Similarity	NPC22628
0.7931	Intermediate Similarity	NPC275696
0.7931	Intermediate Similarity	NPC469488
0.7931	Intermediate Similarity	NPC5991
0.7931	Intermediate Similarity	NPC470777
0.7931	Intermediate Similarity	NPC5989
0.7931	Intermediate Similarity	NPC255081
0.7931	Intermediate Similarity	NPC471108
0.7909	Intermediate Similarity	NPC144854
0.7909	Intermediate Similarity	NPC3316
0.7895	Intermediate Similarity	NPC472400
0.7895	Intermediate Similarity	NPC117712
0.7881	Intermediate Similarity	NPC162009
0.7881	Intermediate Similarity	NPC257017
0.7881	Intermediate Similarity	NPC222688
0.7876	Intermediate Similarity	NPC474516
0.7876	Intermediate Similarity	NPC472002
0.7869	Intermediate Similarity	NPC475314
0.7869	Intermediate Similarity	NPC251564
0.7869	Intermediate Similarity	NPC475606
0.7869	Intermediate Similarity	NPC477189
0.7863	Intermediate Similarity	NPC472004
0.7863	Intermediate Similarity	NPC112038
0.7863	Intermediate Similarity	NPC471128
0.7863	Intermediate Similarity	NPC157252
0.7863	Intermediate Similarity	NPC145182
0.7863	Intermediate Similarity	NPC471126
0.7857	Intermediate Similarity	NPC210005
0.7857	Intermediate Similarity	NPC153036
0.7845	Intermediate Similarity	NPC251310
0.784	Intermediate Similarity	NPC68282
0.7838	Intermediate Similarity	NPC19412
0.7838	Intermediate Similarity	NPC469508
0.7826	Intermediate Similarity	NPC328374
0.7826	Intermediate Similarity	NPC96312
0.7826	Intermediate Similarity	NPC40632
0.7826	Intermediate Similarity	NPC54739
0.7826	Intermediate Similarity	NPC251236
0.7818	Intermediate Similarity	NPC102352
0.7807	Intermediate Similarity	NPC472757
0.7805	Intermediate Similarity	NPC474508
0.7805	Intermediate Similarity	NPC473485
0.7797	Intermediate Similarity	NPC52839
0.7788	Intermediate Similarity	NPC174471
0.7788	Intermediate Similarity	NPC260786
0.7788	Intermediate Similarity	NPC474871
0.7788	Intermediate Similarity	NPC475937
0.7788	Intermediate Similarity	NPC474229
0.7788	Intermediate Similarity	NPC158523
0.7788	Intermediate Similarity	NPC96739
0.7768	Intermediate Similarity	NPC153239
0.7759	Intermediate Similarity	NPC176513
0.7759	Intermediate Similarity	NPC470775
0.775	Intermediate Similarity	NPC24651
0.775	Intermediate Similarity	NPC473255
0.7739	Intermediate Similarity	NPC473798
0.7739	Intermediate Similarity	NPC300051
0.7719	Intermediate Similarity	NPC215643
0.7719	Intermediate Similarity	NPC170212
0.7719	Intermediate Similarity	NPC221511
0.7719	Intermediate Similarity	NPC151216
0.7719	Intermediate Similarity	NPC475391
0.7719	Intermediate Similarity	NPC17138
0.7719	Intermediate Similarity	NPC89227
0.7719	Intermediate Similarity	NPC101825
0.7719	Intermediate Similarity	NPC265499
0.7714	Intermediate Similarity	NPC258674
0.7712	Intermediate Similarity	NPC143755
0.7705	Intermediate Similarity	NPC236999
0.7699	Intermediate Similarity	NPC474567
0.7692	Intermediate Similarity	NPC124676
0.7692	Intermediate Similarity	NPC146280
0.7692	Intermediate Similarity	NPC297179
0.7672	Intermediate Similarity	NPC179626
0.7672	Intermediate Similarity	NPC471127
0.7672	Intermediate Similarity	NPC234858
0.7672	Intermediate Similarity	NPC270478
0.7672	Intermediate Similarity	NPC154363
0.7667	Intermediate Similarity	NPC469352
0.7664	Intermediate Similarity	NPC111348
0.7652	Intermediate Similarity	NPC194273
0.7652	Intermediate Similarity	NPC474937
0.7652	Intermediate Similarity	NPC71889
0.7652	Intermediate Similarity	NPC477126
0.7652	Intermediate Similarity	NPC194100
0.7647	Intermediate Similarity	NPC470921
0.7642	Intermediate Similarity	NPC231529
0.7632	Intermediate Similarity	NPC201992
0.7623	Intermediate Similarity	NPC470882
0.7611	Intermediate Similarity	NPC141350
0.7611	Intermediate Similarity	NPC163004
0.7607	Intermediate Similarity	NPC10721
0.7607	Intermediate Similarity	NPC27999
0.7607	Intermediate Similarity	NPC477116
0.7603	Intermediate Similarity	NPC145238
0.7593	Intermediate Similarity	NPC470541
0.7589	Intermediate Similarity	NPC474716
0.7586	Intermediate Similarity	NPC268238
0.7586	Intermediate Similarity	NPC474872
0.7586	Intermediate Similarity	NPC243354
0.7586	Intermediate Similarity	NPC323821
0.7586	Intermediate Similarity	NPC45218
0.7586	Intermediate Similarity	NPC143268
0.7583	Intermediate Similarity	NPC312833
0.7581	Intermediate Similarity	NPC475389
0.7581	Intermediate Similarity	NPC473838
0.7573	Intermediate Similarity	NPC269677
0.7568	Intermediate Similarity	NPC65523
0.7568	Intermediate Similarity	NPC13385
0.7565	Intermediate Similarity	NPC11252
0.7565	Intermediate Similarity	NPC269530
0.7565	Intermediate Similarity	NPC289312
0.7563	Intermediate Similarity	NPC475885
0.7561	Intermediate Similarity	NPC270109
0.7545	Intermediate Similarity	NPC474747
0.7544	Intermediate Similarity	NPC5103
0.7544	Intermediate Similarity	NPC5284
0.7542	Intermediate Similarity	NPC470776
0.7541	Intermediate Similarity	NPC225049
0.7522	Intermediate Similarity	NPC231278
0.7522	Intermediate Similarity	NPC293850
0.7522	Intermediate Similarity	NPC112895
0.7522	Intermediate Similarity	NPC273155
0.7522	Intermediate Similarity	NPC218123
0.7521	Intermediate Similarity	NPC471392
0.7521	Intermediate Similarity	NPC18945
0.7521	Intermediate Similarity	NPC134869
0.7521	Intermediate Similarity	NPC105926
0.7521	Intermediate Similarity	NPC152199
0.7521	Intermediate Similarity	NPC477509
0.7521	Intermediate Similarity	NPC265557
0.7521	Intermediate Similarity	NPC235539
0.7521	Intermediate Similarity	NPC67251
0.7521	Intermediate Similarity	NPC173686
0.7521	Intermediate Similarity	NPC16081
0.7521	Intermediate Similarity	NPC91693
0.75	Intermediate Similarity	NPC51978
0.75	Intermediate Similarity	NPC190867
0.75	Intermediate Similarity	NPC314244
0.75	Intermediate Similarity	NPC472655
0.75	Intermediate Similarity	NPC52634
0.75	Intermediate Similarity	NPC181357
0.75	Intermediate Similarity	NPC470120
0.75	Intermediate Similarity	NPC236176
0.75	Intermediate Similarity	NPC264192
0.75	Intermediate Similarity	NPC472000
0.75	Intermediate Similarity	NPC471999
0.75	Intermediate Similarity	NPC470779
0.75	Intermediate Similarity	NPC198539
0.75	Intermediate Similarity	NPC310511
0.748	Intermediate Similarity	NPC473265
0.748	Intermediate Similarity	NPC473253

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 NPC29827 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	202
0.1-0.2	1882
0.2-0.3	3921
0.3-0.4	2031
0.4-0.5	736
0.5-0.6	209
0.6-0.7	153
0.7-0.8	16
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
0.7563	Intermediate Similarity	NPD6319	Approved
0.7459	Intermediate Similarity	NPD7492	Approved
0.7417	Intermediate Similarity	NPD6054	Approved
0.7398	Intermediate Similarity	NPD6616	Approved
0.7355	Intermediate Similarity	NPD6015	Approved
0.7355	Intermediate Similarity	NPD6016	Approved
0.735	Intermediate Similarity	NPD4632	Approved
0.7339	Intermediate Similarity	NPD7078	Approved
0.7295	Intermediate Similarity	NPD6370	Approved
0.7295	Intermediate Similarity	NPD5988	Approved
0.7281	Intermediate Similarity	NPD7899	Clinical (unspecified phase)
0.728	Intermediate Similarity	NPD7736	Approved
0.7273	Intermediate Similarity	NPD6059	Approved
0.7217	Intermediate Similarity	NPD5345	Clinical (unspecified phase)
0.72	Intermediate Similarity	NPD8293	Discontinued
0.7193	Intermediate Similarity	NPD6008	Approved
0.7179	Intermediate Similarity	NPD6650	Approved
0.7179	Intermediate Similarity	NPD6649	Approved
0.7155	Intermediate Similarity	NPD6372	Approved
0.7155	Intermediate Similarity	NPD6373	Approved
0.713	Intermediate Similarity	NPD5697	Approved
0.7119	Intermediate Similarity	NPD8297	Approved
0.7094	Intermediate Similarity	NPD4634	Approved
0.7069	Intermediate Similarity	NPD7320	Approved
0.7069	Intermediate Similarity	NPD6899	Approved
0.7069	Intermediate Similarity	NPD6881	Approved
0.7064	Intermediate Similarity	NPD5282	Discontinued
0.7043	Intermediate Similarity	NPD6675	Approved
0.7043	Intermediate Similarity	NPD7128	Approved
0.7043	Intermediate Similarity	NPD5739	Approved
0.7043	Intermediate Similarity	NPD6402	Approved
0.7025	Intermediate Similarity	NPD6009	Approved
0.7009	Intermediate Similarity	NPD6014	Approved
0.7009	Intermediate Similarity	NPD6012	Approved
0.7009	Intermediate Similarity	NPD6013	Approved
0.6991	Remote Similarity	NPD1700	Approved
0.6983	Remote Similarity	NPD5701	Approved
0.6949	Remote Similarity	NPD6883	Approved
0.6949	Remote Similarity	NPD7290	Approved
0.6949	Remote Similarity	NPD7102	Approved
0.6935	Remote Similarity	NPD5983	Phase 2
0.6923	Remote Similarity	NPD6011	Approved
0.6891	Remote Similarity	NPD8130	Phase 1
0.6891	Remote Similarity	NPD6869	Approved
0.6891	Remote Similarity	NPD6617	Approved
0.6891	Remote Similarity	NPD6847	Approved
0.6847	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6833	Remote Similarity	NPD6882	Approved
0.6825	Remote Similarity	NPD7604	Phase 2
0.6825	Remote Similarity	NPD8328	Phase 3
0.6822	Remote Similarity	NPD7319	Approved
0.6814	Remote Similarity	NPD4225	Approved
0.6807	Remote Similarity	NPD6371	Approved
0.6807	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6754	Remote Similarity	NPD5285	Approved
0.6754	Remote Similarity	NPD5286	Approved
0.6754	Remote Similarity	NPD4696	Approved
0.6748	Remote Similarity	NPD7115	Discovery
0.6744	Remote Similarity	NPD6033	Approved
0.6726	Remote Similarity	NPD4755	Approved
0.6723	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6719	Remote Similarity	NPD6336	Discontinued
0.6696	Remote Similarity	NPD5695	Phase 3
0.6696	Remote Similarity	NPD5344	Discontinued
0.6667	Remote Similarity	NPD5696	Approved
0.6667	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6274	Approved
0.6638	Remote Similarity	NPD5225	Approved
0.6638	Remote Similarity	NPD5226	Approved
0.6638	Remote Similarity	NPD5224	Approved
0.6638	Remote Similarity	NPD5211	Phase 2
0.6638	Remote Similarity	NPD4633	Approved
0.6612	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6609	Remote Similarity	NPD4700	Approved
0.6589	Remote Similarity	NPD7507	Approved
0.6581	Remote Similarity	NPD5174	Approved
0.6581	Remote Similarity	NPD5175	Approved
0.6579	Remote Similarity	NPD6083	Phase 2
0.6579	Remote Similarity	NPD6084	Phase 2
0.6555	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6552	Remote Similarity	NPD5223	Approved
0.6549	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6545	Remote Similarity	NPD1695	Approved
0.6535	Remote Similarity	NPD6921	Approved
0.6525	Remote Similarity	NPD5141	Approved
0.6518	Remote Similarity	NPD6399	Phase 3
0.6514	Remote Similarity	NPD3573	Approved
0.6509	Remote Similarity	NPD4800	Clinical (unspecified phase)
0.6508	Remote Similarity	NPD7100	Approved
0.6508	Remote Similarity	NPD7101	Approved
0.6491	Remote Similarity	NPD4697	Phase 3
0.648	Remote Similarity	NPD6317	Approved
0.648	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6466	Remote Similarity	NPD6648	Approved
0.646	Remote Similarity	NPD6001	Approved
0.6435	Remote Similarity	NPD7902	Approved
0.6429	Remote Similarity	NPD6314	Approved
0.6429	Remote Similarity	NPD6313	Approved
0.6429	Remote Similarity	NPD5284	Approved
0.6429	Remote Similarity	NPD6335	Approved
0.6429	Remote Similarity	NPD5281	Approved
0.6423	Remote Similarity	NPD6053	Discontinued
0.6422	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6396	Remote Similarity	NPD6904	Approved
0.6396	Remote Similarity	NPD6673	Approved
0.6396	Remote Similarity	NPD6080	Approved
0.6378	Remote Similarity	NPD7516	Approved
0.6364	Remote Similarity	NPD5128	Approved
0.6364	Remote Similarity	NPD4729	Approved
0.6364	Remote Similarity	NPD4730	Approved
0.6348	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6348	Remote Similarity	NPD5222	Approved
0.6348	Remote Similarity	NPD5221	Approved
0.6339	Remote Similarity	NPD5692	Phase 3
0.6339	Remote Similarity	NPD5207	Approved
0.6333	Remote Similarity	NPD4768	Approved
0.6333	Remote Similarity	NPD4767	Approved
0.633	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.6311	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6303	Remote Similarity	NPD4754	Approved
0.6299	Remote Similarity	NPD7328	Approved
0.6299	Remote Similarity	NPD7327	Approved
0.6293	Remote Similarity	NPD5173	Approved
0.6283	Remote Similarity	NPD5694	Approved
0.6283	Remote Similarity	NPD5693	Phase 1
0.6283	Remote Similarity	NPD6050	Approved
0.6283	Remote Similarity	NPD7983	Approved
0.6281	Remote Similarity	NPD6412	Phase 2
0.6279	Remote Similarity	NPD6908	Approved
0.6279	Remote Similarity	NPD8513	Phase 3
0.6279	Remote Similarity	NPD8517	Approved
0.6279	Remote Similarity	NPD6909	Approved
0.6279	Remote Similarity	NPD8516	Approved
0.6279	Remote Similarity	NPD8515	Approved
0.6273	Remote Similarity	NPD5690	Phase 2
0.6269	Remote Similarity	NPD5956	Approved
0.6261	Remote Similarity	NPD4629	Approved
0.6261	Remote Similarity	NPD5210	Approved
0.626	Remote Similarity	NPD5250	Approved
0.626	Remote Similarity	NPD5248	Approved
0.626	Remote Similarity	NPD5249	Phase 3
0.626	Remote Similarity	NPD5247	Approved
0.626	Remote Similarity	NPD5251	Approved
0.625	Remote Similarity	NPD4753	Phase 2
0.6239	Remote Similarity	NPD7638	Approved
0.6239	Remote Similarity	NPD4197	Approved
0.623	Remote Similarity	NPD6686	Approved
0.6228	Remote Similarity	NPD5779	Approved
0.6228	Remote Similarity	NPD5778	Approved
0.621	Remote Similarity	NPD5217	Approved
0.621	Remote Similarity	NPD5215	Approved
0.621	Remote Similarity	NPD5216	Approved
0.6195	Remote Similarity	NPD46	Approved
0.6195	Remote Similarity	NPD6698	Approved
0.6187	Remote Similarity	NPD6333	Approved
0.6187	Remote Similarity	NPD6334	Approved
0.6186	Remote Similarity	NPD7639	Approved
0.6186	Remote Similarity	NPD7640	Approved
0.6182	Remote Similarity	NPD5329	Approved
0.6176	Remote Similarity	NPD8338	Approved
0.6174	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6174	Remote Similarity	NPD7748	Approved
0.6174	Remote Similarity	NPD7900	Approved
0.6168	Remote Similarity	NPD4695	Discontinued
0.6161	Remote Similarity	NPD6672	Approved
0.6161	Remote Similarity	NPD5737	Approved
0.6142	Remote Similarity	NPD6868	Approved
0.614	Remote Similarity	NPD6079	Approved
0.6129	Remote Similarity	NPD5135	Approved
0.6129	Remote Similarity	NPD5169	Approved
0.6129	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.6126	Remote Similarity	NPD4694	Approved
0.6126	Remote Similarity	NPD6098	Approved
0.6126	Remote Similarity	NPD5280	Approved
0.6106	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6106	Remote Similarity	NPD5328	Approved
0.6106	Remote Similarity	NPD6101	Approved
0.6087	Remote Similarity	NPD4202	Approved
0.608	Remote Similarity	NPD5127	Approved
0.6055	Remote Similarity	NPD4221	Approved
0.6055	Remote Similarity	NPD4223	Phase 3
0.6045	Remote Similarity	NPD8074	Phase 3
0.6036	Remote Similarity	NPD1694	Approved
0.6031	Remote Similarity	NPD8378	Approved
0.6031	Remote Similarity	NPD8335	Approved
0.6031	Remote Similarity	NPD8033	Approved
0.6031	Remote Similarity	NPD8296	Approved
0.6031	Remote Similarity	NPD8380	Approved
0.6031	Remote Similarity	NPD8379	Approved
0.6018	Remote Similarity	NPD5208	Approved
0.6	Remote Similarity	NPD4522	Approved
0.6	Remote Similarity	NPD7515	Phase 2
0.6	Remote Similarity	NPD8035	Phase 2
0.6	Remote Similarity	NPD8034	Phase 2
0.6	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.6	Remote Similarity	NPD6411	Approved
0.5985	Remote Similarity	NPD7260	Phase 2
0.5983	Remote Similarity	NPD5654	Approved
0.5982	Remote Similarity	NPD5786	Approved
0.5982	Remote Similarity	NPD3618	Phase 1

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