NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	248.14
Volume:	266.708
LogP:	2.662
LogD:	1.131
LogS:	-2.89
# Rotatable Bonds:	2
TPSA:	54.37
# H-Bond Aceptor:	3
# H-Bond Donor:	1
# Rings:	2
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.603
Synthetic Accessibility Score:	4.272
Fsp3:	0.6
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	2
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.052
MDCK Permeability:	1.3637511074193753e-05
Pgp-inhibitor:	0.001
Pgp-substrate:	0.002
Human Intestinal Absorption (HIA):	0.266
20% Bioavailability (F20%):	0.247
30% Bioavailability (F30%):	0.003

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.043
Plasma Protein Binding (PPB):	91.91971588134766%
Volume Distribution (VD):	0.414
Pgp-substrate:	5.088048934936523%

ADMET: Metabolism

CYP1A2-inhibitor:	0.036
CYP1A2-substrate:	0.119
CYP2C19-inhibitor:	0.023
CYP2C19-substrate:	0.064
CYP2C9-inhibitor:	0.119
CYP2C9-substrate:	0.899
CYP2D6-inhibitor:	0.008
CYP2D6-substrate:	0.258
CYP3A4-inhibitor:	0.014
CYP3A4-substrate:	0.233

ADMET: Excretion

Clearance (CL):	5.26
Half-life (T1/2):	0.746

ADMET: Toxicity

hERG Blockers:	0.015
Human Hepatotoxicity (H-HT):	0.168
Drug-inuced Liver Injury (DILI):	0.963
AMES Toxicity:	0.012
Rat Oral Acute Toxicity:	0.651
Maximum Recommended Daily Dose:	0.17
Skin Sensitization:	0.709
Carcinogencity:	0.772
Eye Corrosion:	0.438
Eye Irritation:	0.825
Respiratory Toxicity:	0.924

Download Data

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

Natural Product: NPC29328

Natural Product ID:	NPC29328
*Common Name:**	Pechueloic Acid
IUPAC Name:	2-[(5R,8S,8aS)-3,8-dimethyl-2-oxo-4,5,6,7,8,8a-hexahydro-1H-azulen-5-yl]prop-2-enoic acid
Synonyms:	Pechueloic Acid
Standard InCHIKey:	ZFHSKBJBODQVBX-AXTRIDKLSA-N
Standard InCHI:	InChI=1S/C15H20O3/c1-8-4-5-11(9(2)15(17)18)6-13-10(3)14(16)7-12(8)13/h8,11-12H,2,4-7H2,1,3H3,(H,17,18)/p-1/t8-,11+,12-/m0/s1
SMILES:	C[C@H]1CC[C@H](CC2=C(C)C(=O)C[C@@H]12)C(=C)C(=O)[O-]
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1956398
PubChem CID:	24094149
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001550] Sesquiterpenoids [CHEMONTID:0002874] Guaianes

*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
NPO12728	Artemisia rupestris	Species	Asteraceae	Eukaryota	Whole plant	n.a.	n.a.	PMID[25127164]
NPO12728	Artemisia rupestris	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25176187]
NPO12728	Artemisia rupestris	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26696523]
NPO12728	Artemisia rupestris	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO12728	Artemisia rupestris	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO12728	Artemisia rupestris	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO12728	Artemisia rupestris	Species	Asteraceae	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	12
Others	15

Activity Type	# Activity
Cell Line	5
Organism	11
Others	11

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT616	Cell Line	MDCK	Canis lupus familiaris	TC50	=	4653.0	uM	PMID[479457]
NPT616	Cell Line	MDCK	Canis lupus familiaris	TC50	=	248.0	ug ml-1	PMID[479458]
NPT113	Cell Line	RAW264.7	Mus musculus	IC50	=	3040.0	nM	PMID[479459]
NPT616	Cell Line	MDCK	Canis lupus familiaris	TC50	=	240.37	ug ml-1	PMID[479460]
NPT616	Cell Line	MDCK	Canis lupus familiaris	TC50	=	969.6	uM	PMID[479461]
NPT742	Organism	Influenza A virus	Influenza A virus	IC50	=	25800.0	nM	PMID[479457]
NPT742	Organism	Influenza A virus	Influenza A virus	IC50	>	1344000.0	nM	PMID[479457]
NPT4249	Organism	Influenza B virus	Influenza B virus	IC50	>	4032000.0	nM	PMID[479457]
NPT2	Others	Unspecified		Selectivity Index	=	180.6	n.a.	PMID[479457]
NPT2	Others	Unspecified		Selectivity Index	>	4032.0	n.a.	PMID[479458]
NPT4249	Organism	Influenza B virus	Influenza B virus	IC50	=	180.6	ug.mL-1	PMID[479458]
NPT2	Others	Unspecified		Selectivity Index	=	25.8	n.a.	PMID[479458]
NPT2	Others	Unspecified		Selectivity Index	>	1344.0	n.a.	PMID[479458]
NPT2	Others	Unspecified		Selectivity Index	>	111.1	n.a.	PMID[479458]
NPT742	Organism	Influenza A virus	Influenza A virus	IC50	=	4653.0	ug.mL-1	PMID[479458]
NPT339	Organism	Influenza A virus H3N2	Influenza A virus H3N2	IC50	=	55.56	ug.mL-1	PMID[479460]
NPT742	Organism	Influenza A virus	Influenza A virus	IC50	=	55.56	ug.mL-1	PMID[479460]
NPT4249	Organism	Influenza B virus	Influenza B virus	IC50	=	24.0	ug.mL-1	PMID[479460]
NPT2	Others	Unspecified		Selectivity Index	=	4.3	n.a.	PMID[479460]
NPT2	Others	Unspecified		Selectivity Index	=	10.0	n.a.	PMID[479460]
NPT2	Others	Unspecified		Selectivity Index	=	10.0	n.a.	PMID[479461]
NPT4249	Organism	Influenza B virus	Influenza B virus	IC50	=	97700.0	nM	PMID[479461]
NPT2	Others	Unspecified		Selectivity Index	=	4.3	n.a.	PMID[479461]
NPT339	Organism	Influenza A virus H3N2	Influenza A virus H3N2	IC50	=	224500.0	nM	PMID[479461]
NPT742	Organism	Influenza A virus	Influenza A virus	IC50	=	224300.0	nM	PMID[479461]

☑ 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 NPC29328 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	177
0.1-0.2	1497
0.2-0.3	8521
0.3-0.4	16960
0.4-0.5	8529
0.5-0.6	5208
0.6-0.7	1604
0.7-0.8	181
0.8-0.85	10
0.85-0.9	5
0.9-0.95	4
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9296	High Similarity	NPC472014
0.9118	High Similarity	NPC67608
0.9104	High Similarity	NPC476626
0.9041	High Similarity	NPC472013
0.9041	High Similarity	NPC476624
0.8714	High Similarity	NPC18543
0.8696	High Similarity	NPC476614
0.8649	High Similarity	NPC476627
0.8611	High Similarity	NPC7382
0.8592	High Similarity	NPC288667
0.8429	Intermediate Similarity	NPC476629
0.8354	Intermediate Similarity	NPC476628
0.8158	Intermediate Similarity	NPC192006
0.8101	Intermediate Similarity	NPC65350
0.8082	Intermediate Similarity	NPC469737
0.8026	Intermediate Similarity	NPC97377
0.8	Intermediate Similarity	NPC474329
0.8	Intermediate Similarity	NPC474304
0.8	Intermediate Similarity	NPC89374
0.7949	Intermediate Similarity	NPC69271
0.7949	Intermediate Similarity	NPC74673
0.7945	Intermediate Similarity	NPC280256
0.7922	Intermediate Similarity	NPC169095
0.7895	Intermediate Similarity	NPC182848
0.7887	Intermediate Similarity	NPC308294
0.7887	Intermediate Similarity	NPC142423
0.7879	Intermediate Similarity	NPC20603
0.7778	Intermediate Similarity	NPC60120
0.7763	Intermediate Similarity	NPC474011
0.7733	Intermediate Similarity	NPC300940
0.7733	Intermediate Similarity	NPC35656
0.7711	Intermediate Similarity	NPC237540
0.7662	Intermediate Similarity	NPC279537
0.7662	Intermediate Similarity	NPC469646
0.7662	Intermediate Similarity	NPC473223
0.7639	Intermediate Similarity	NPC322035
0.7639	Intermediate Similarity	NPC100719
0.7639	Intermediate Similarity	NPC166791
0.7639	Intermediate Similarity	NPC197089
0.7625	Intermediate Similarity	NPC171665
0.7606	Intermediate Similarity	NPC470325
0.7606	Intermediate Similarity	NPC53642
0.76	Intermediate Similarity	NPC67076
0.76	Intermediate Similarity	NPC319163
0.7595	Intermediate Similarity	NPC471890
0.7595	Intermediate Similarity	NPC84185
0.7595	Intermediate Similarity	NPC66677
0.759	Intermediate Similarity	NPC472869
0.7571	Intermediate Similarity	NPC125312
0.7571	Intermediate Similarity	NPC174560
0.7564	Intermediate Similarity	NPC195785
0.7564	Intermediate Similarity	NPC15975
0.7561	Intermediate Similarity	NPC472864
0.7561	Intermediate Similarity	NPC165287
0.7561	Intermediate Similarity	NPC472958
0.7561	Intermediate Similarity	NPC472957
0.7561	Intermediate Similarity	NPC19849
0.7561	Intermediate Similarity	NPC472865
0.7561	Intermediate Similarity	NPC248758
0.7534	Intermediate Similarity	NPC472875
0.7532	Intermediate Similarity	NPC476795
0.7532	Intermediate Similarity	NPC77501
0.7532	Intermediate Similarity	NPC472327
0.7532	Intermediate Similarity	NPC251435
0.7529	Intermediate Similarity	NPC268298
0.75	Intermediate Similarity	NPC824
0.75	Intermediate Similarity	NPC302426
0.75	Intermediate Similarity	NPC138492
0.75	Intermediate Similarity	NPC45495
0.75	Intermediate Similarity	NPC276356
0.75	Intermediate Similarity	NPC271104
0.75	Intermediate Similarity	NPC233352
0.75	Intermediate Similarity	NPC275098
0.75	Intermediate Similarity	NPC476625
0.7471	Intermediate Similarity	NPC135776
0.747	Intermediate Similarity	NPC125290
0.747	Intermediate Similarity	NPC142649
0.7468	Intermediate Similarity	NPC172066
0.7468	Intermediate Similarity	NPC198240
0.7468	Intermediate Similarity	NPC299235
0.7468	Intermediate Similarity	NPC74410
0.7467	Intermediate Similarity	NPC67183
0.7467	Intermediate Similarity	NPC318766
0.7465	Intermediate Similarity	NPC322457
0.7442	Intermediate Similarity	NPC77337
0.7442	Intermediate Similarity	NPC472866
0.7442	Intermediate Similarity	NPC129419
0.7439	Intermediate Similarity	NPC49019
0.7439	Intermediate Similarity	NPC97913
0.7439	Intermediate Similarity	NPC39588
0.7436	Intermediate Similarity	NPC472967
0.7436	Intermediate Similarity	NPC180886
0.7436	Intermediate Similarity	NPC215481
0.7436	Intermediate Similarity	NPC266159
0.7424	Intermediate Similarity	NPC474141
0.7412	Intermediate Similarity	NPC91248
0.7412	Intermediate Similarity	NPC472870
0.7407	Intermediate Similarity	NPC10276
0.7407	Intermediate Similarity	NPC470241
0.7407	Intermediate Similarity	NPC35089
0.7407	Intermediate Similarity	NPC477372
0.7407	Intermediate Similarity	NPC325031
0.7403	Intermediate Similarity	NPC472966
0.7403	Intermediate Similarity	NPC213223
0.7397	Intermediate Similarity	NPC81907
0.7386	Intermediate Similarity	NPC167219
0.7375	Intermediate Similarity	NPC469617
0.7375	Intermediate Similarity	NPC229204
0.7375	Intermediate Similarity	NPC470244
0.7375	Intermediate Similarity	NPC470239
0.7375	Intermediate Similarity	NPC7232
0.7368	Intermediate Similarity	NPC21944
0.7368	Intermediate Similarity	NPC106309
0.7361	Intermediate Similarity	NPC234767
0.7349	Intermediate Similarity	NPC164577
0.7349	Intermediate Similarity	NPC156485
0.7342	Intermediate Similarity	NPC165711
0.7342	Intermediate Similarity	NPC86917
0.7342	Intermediate Similarity	NPC316324
0.7342	Intermediate Similarity	NPC61952
0.7333	Intermediate Similarity	NPC144511
0.7333	Intermediate Similarity	NPC469914
0.7333	Intermediate Similarity	NPC296522
0.7326	Intermediate Similarity	NPC232747
0.7326	Intermediate Similarity	NPC170775
0.7326	Intermediate Similarity	NPC262043
0.7326	Intermediate Similarity	NPC477215
0.7326	Intermediate Similarity	NPC476388
0.7317	Intermediate Similarity	NPC320514
0.7317	Intermediate Similarity	NPC256750
0.7317	Intermediate Similarity	NPC472867
0.7317	Intermediate Similarity	NPC20262
0.7317	Intermediate Similarity	NPC133844
0.7308	Intermediate Similarity	NPC138408
0.7308	Intermediate Similarity	NPC216791
0.7308	Intermediate Similarity	NPC244166
0.7308	Intermediate Similarity	NPC193351
0.7308	Intermediate Similarity	NPC226669
0.7297	Intermediate Similarity	NPC278895
0.7294	Intermediate Similarity	NPC136948
0.7286	Intermediate Similarity	NPC274927
0.7286	Intermediate Similarity	NPC106851
0.7284	Intermediate Similarity	NPC164218
0.7273	Intermediate Similarity	NPC472956
0.7262	Intermediate Similarity	NPC33570
0.7262	Intermediate Similarity	NPC161957
0.7262	Intermediate Similarity	NPC29447
0.7262	Intermediate Similarity	NPC165162
0.7262	Intermediate Similarity	NPC21471
0.725	Intermediate Similarity	NPC475994
0.725	Intermediate Similarity	NPC108816
0.725	Intermediate Similarity	NPC128276
0.725	Intermediate Similarity	NPC62336
0.725	Intermediate Similarity	NPC19443
0.725	Intermediate Similarity	NPC93763
0.7237	Intermediate Similarity	NPC235586
0.7229	Intermediate Similarity	NPC470165
0.7229	Intermediate Similarity	NPC470015
0.7229	Intermediate Similarity	NPC215294
0.7229	Intermediate Similarity	NPC168188
0.7222	Intermediate Similarity	NPC185553
0.7215	Intermediate Similarity	NPC472305
0.7215	Intermediate Similarity	NPC115719
0.7215	Intermediate Similarity	NPC142759
0.7215	Intermediate Similarity	NPC263582
0.7215	Intermediate Similarity	NPC473437
0.7215	Intermediate Similarity	NPC151622
0.7215	Intermediate Similarity	NPC141346
0.7215	Intermediate Similarity	NPC124289
0.7215	Intermediate Similarity	NPC472959
0.7215	Intermediate Similarity	NPC25908
0.7215	Intermediate Similarity	NPC7629
0.7209	Intermediate Similarity	NPC117122
0.7209	Intermediate Similarity	NPC193843
0.7209	Intermediate Similarity	NPC249889
0.7195	Intermediate Similarity	NPC39411
0.7195	Intermediate Similarity	NPC278459
0.7195	Intermediate Similarity	NPC136150
0.7195	Intermediate Similarity	NPC90055
0.7195	Intermediate Similarity	NPC47031
0.7195	Intermediate Similarity	NPC255580
0.7195	Intermediate Similarity	NPC78677
0.7195	Intermediate Similarity	NPC59994
0.7191	Intermediate Similarity	NPC262133
0.7191	Intermediate Similarity	NPC323008
0.7191	Intermediate Similarity	NPC470013
0.7191	Intermediate Similarity	NPC198853
0.7191	Intermediate Similarity	NPC477131
0.7191	Intermediate Similarity	NPC470010
0.7183	Intermediate Similarity	NPC472328
0.7183	Intermediate Similarity	NPC235242
0.7183	Intermediate Similarity	NPC122521
0.7183	Intermediate Similarity	NPC251042
0.7183	Intermediate Similarity	NPC174447
0.7179	Intermediate Similarity	NPC469641
0.7179	Intermediate Similarity	NPC206875
0.7179	Intermediate Similarity	NPC227396
0.7179	Intermediate Similarity	NPC469643
0.7176	Intermediate Similarity	NPC107787
0.7176	Intermediate Similarity	NPC186975

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 NPC29328 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	170
0.1-0.2	2272
0.2-0.3	4085
0.3-0.4	1841
0.4-0.5	512
0.5-0.6	228
0.6-0.7	40
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
0.747	Intermediate Similarity	NPD5363	Approved
0.725	Intermediate Similarity	NPD5784	Clinical (unspecified phase)
0.7229	Intermediate Similarity	NPD5362	Discontinued
0.7162	Intermediate Similarity	NPD7331	Phase 2
0.7111	Intermediate Similarity	NPD1698	Clinical (unspecified phase)
0.7108	Intermediate Similarity	NPD4270	Approved
0.7108	Intermediate Similarity	NPD4269	Approved
0.7045	Intermediate Similarity	NPD5785	Approved
0.7027	Intermediate Similarity	NPD7341	Phase 2
0.7024	Intermediate Similarity	NPD7154	Phase 3
0.6867	Remote Similarity	NPD4252	Approved
0.6867	Remote Similarity	NPD5368	Approved
0.6786	Remote Similarity	NPD5369	Approved
0.6782	Remote Similarity	NPD4623	Approved
0.6782	Remote Similarity	NPD5786	Approved
0.6782	Remote Similarity	NPD4519	Discontinued
0.6742	Remote Similarity	NPD1695	Approved
0.6707	Remote Similarity	NPD4756	Discovery
0.6706	Remote Similarity	NPD4221	Approved
0.6706	Remote Similarity	NPD6435	Approved
0.6706	Remote Similarity	NPD4223	Phase 3
0.6667	Remote Similarity	NPD4821	Approved
0.6667	Remote Similarity	NPD3172	Approved
0.6667	Remote Similarity	NPD4695	Discontinued
0.6667	Remote Similarity	NPD4819	Approved
0.6667	Remote Similarity	NPD4820	Approved
0.6667	Remote Similarity	NPD4822	Approved
0.6628	Remote Similarity	NPD5332	Approved
0.6628	Remote Similarity	NPD5331	Approved
0.6627	Remote Similarity	NPD4268	Approved
0.6627	Remote Similarity	NPD4271	Approved
0.6627	Remote Similarity	NPD3617	Approved
0.6593	Remote Similarity	NPD5281	Approved
0.6593	Remote Similarity	NPD5284	Approved
0.6591	Remote Similarity	NPD5690	Phase 2
0.6588	Remote Similarity	NPD857	Phase 3
0.6588	Remote Similarity	NPD4790	Discontinued
0.6571	Remote Similarity	NPD4266	Approved
0.6571	Remote Similarity	NPD3195	Phase 2
0.6571	Remote Similarity	NPD3196	Approved
0.6571	Remote Similarity	NPD3194	Approved
0.6552	Remote Similarity	NPD3666	Approved
0.6552	Remote Similarity	NPD3665	Phase 1
0.6552	Remote Similarity	NPD3133	Approved
0.6552	Remote Similarity	NPD4197	Approved
0.6533	Remote Similarity	NPD2664	Clinical (unspecified phase)
0.6512	Remote Similarity	NPD4800	Clinical (unspecified phase)
0.6512	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6477	Remote Similarity	NPD5329	Approved
0.6477	Remote Similarity	NPD1694	Approved
0.6471	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6404	Remote Similarity	NPD7146	Approved
0.6404	Remote Similarity	NPD6409	Approved
0.6404	Remote Similarity	NPD4690	Approved
0.6404	Remote Similarity	NPD5279	Phase 3
0.6404	Remote Similarity	NPD5280	Approved
0.6404	Remote Similarity	NPD4689	Approved
0.6404	Remote Similarity	NPD7521	Approved
0.6404	Remote Similarity	NPD5205	Approved
0.6404	Remote Similarity	NPD7334	Approved
0.6404	Remote Similarity	NPD4138	Approved
0.6404	Remote Similarity	NPD4693	Phase 3
0.6404	Remote Similarity	NPD4688	Approved
0.6404	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6404	Remote Similarity	NPD5330	Approved
0.6404	Remote Similarity	NPD4694	Approved
0.6404	Remote Similarity	NPD3618	Phase 1
0.6404	Remote Similarity	NPD6684	Approved
0.64	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6383	Remote Similarity	NPD5695	Phase 3
0.6375	Remote Similarity	NPD4691	Approved
0.6373	Remote Similarity	NPD6371	Approved
0.6364	Remote Similarity	NPD634	Phase 3
0.6322	Remote Similarity	NPD5209	Approved
0.6322	Remote Similarity	NPD3667	Approved
0.6292	Remote Similarity	NPD1696	Phase 3
0.6289	Remote Similarity	NPD6404	Discontinued
0.6264	Remote Similarity	NPD6672	Approved
0.6264	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6264	Remote Similarity	NPD6903	Approved
0.6264	Remote Similarity	NPD5737	Approved
0.6264	Remote Similarity	NPD4518	Approved
0.6264	Remote Similarity	NPD5208	Approved
0.625	Remote Similarity	NPD6083	Phase 2
0.625	Remote Similarity	NPD6084	Phase 2
0.625	Remote Similarity	NPD4137	Phase 3
0.6237	Remote Similarity	NPD7515	Phase 2
0.6237	Remote Similarity	NPD5693	Phase 1
0.6237	Remote Similarity	NPD6079	Approved
0.6196	Remote Similarity	NPD6673	Approved
0.6196	Remote Similarity	NPD6080	Approved
0.6196	Remote Similarity	NPD4753	Phase 2
0.6196	Remote Similarity	NPD5328	Approved
0.6196	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6196	Remote Similarity	NPD6904	Approved
0.6186	Remote Similarity	NPD5696	Approved
0.618	Remote Similarity	NPD4786	Approved
0.6176	Remote Similarity	NPD622	Approved
0.6173	Remote Similarity	NPD4747	Approved
0.617	Remote Similarity	NPD6399	Phase 3
0.6163	Remote Similarity	NPD4195	Approved
0.6154	Remote Similarity	NPD3573	Approved
0.6145	Remote Similarity	NPD4058	Approved
0.6143	Remote Similarity	NPD29	Approved
0.6143	Remote Similarity	NPD28	Approved
0.6133	Remote Similarity	NPD3198	Approved
0.6129	Remote Similarity	NPD4096	Approved
0.6129	Remote Similarity	NPD5207	Approved
0.6129	Remote Similarity	NPD5692	Phase 3
0.6129	Remote Similarity	NPD6698	Approved
0.6129	Remote Similarity	NPD46	Approved
0.6111	Remote Similarity	NPD615	Clinical (unspecified phase)
0.6111	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6111	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.6105	Remote Similarity	NPD5122	Clinical (unspecified phase)
0.6105	Remote Similarity	NPD7748	Approved
0.6098	Remote Similarity	NPD5276	Approved
0.6087	Remote Similarity	NPD3173	Approved
0.6067	Remote Similarity	NPD4788	Approved
0.6064	Remote Similarity	NPD5694	Approved
0.6064	Remote Similarity	NPD6050	Approved
0.6044	Remote Similarity	NPD6098	Approved
0.6044	Remote Similarity	NPD4249	Approved
0.6042	Remote Similarity	NPD5210	Approved
0.6042	Remote Similarity	NPD4629	Approved
0.6026	Remote Similarity	NPD3197	Phase 1
0.6023	Remote Similarity	NPD4692	Approved
0.6023	Remote Similarity	NPD4139	Approved
0.6	Remote Similarity	NPD5211	Phase 2
0.6	Remote Similarity	NPD4202	Approved
0.6	Remote Similarity	NPD5779	Approved
0.6	Remote Similarity	NPD5778	Approved
0.5979	Remote Similarity	NPD5221	Approved
0.5979	Remote Similarity	NPD5222	Approved
0.5979	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.5979	Remote Similarity	NPD7614	Phase 1
0.5978	Remote Similarity	NPD4251	Approved
0.5978	Remote Similarity	NPD4250	Approved
0.5974	Remote Similarity	NPD4192	Approved
0.5974	Remote Similarity	NPD4193	Approved
0.5974	Remote Similarity	NPD4194	Approved
0.5974	Remote Similarity	NPD4191	Approved
0.596	Remote Similarity	NPD7639	Approved
0.596	Remote Similarity	NPD2066	Phase 3
0.596	Remote Similarity	NPD7640	Approved
0.5952	Remote Similarity	NPD4687	Approved
0.5952	Remote Similarity	NPD5733	Approved
0.5949	Remote Similarity	NPD2685	Clinical (unspecified phase)
0.5941	Remote Similarity	NPD6647	Phase 2
0.5938	Remote Similarity	NPD5282	Discontinued
0.5938	Remote Similarity	NPD6001	Approved
0.5934	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.5922	Remote Similarity	NPD5697	Approved
0.5918	Remote Similarity	NPD5173	Approved
0.5918	Remote Similarity	NPD7902	Approved
0.5895	Remote Similarity	NPD7983	Approved
0.589	Remote Similarity	NPD9298	Approved
0.5882	Remote Similarity	NPD5141	Approved
0.5882	Remote Similarity	NPD8039	Approved
0.5876	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.5876	Remote Similarity	NPD1693	Approved
0.5875	Remote Similarity	NPD6108	Clinical (unspecified phase)
0.5875	Remote Similarity	NPD3704	Approved
0.5865	Remote Similarity	NPD6899	Approved
0.5865	Remote Similarity	NPD6011	Approved
0.5865	Remote Similarity	NPD6881	Approved
0.5859	Remote Similarity	NPD4225	Approved
0.5859	Remote Similarity	NPD7638	Approved
0.5851	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.5851	Remote Similarity	NPD5370	Suspended
0.5851	Remote Similarity	NPD6101	Approved
0.5844	Remote Similarity	NPD4246	Clinical (unspecified phase)
0.5833	Remote Similarity	NPD5133	Approved
0.5833	Remote Similarity	NPD3186	Phase 1
0.5825	Remote Similarity	NPD6402	Approved
0.5825	Remote Similarity	NPD7128	Approved
0.5825	Remote Similarity	NPD5739	Approved
0.5825	Remote Similarity	NPD6675	Approved
0.5824	Remote Similarity	NPD3668	Phase 3
0.5816	Remote Similarity	NPD4697	Phase 3
0.581	Remote Similarity	NPD6012	Approved
0.581	Remote Similarity	NPD6014	Approved
0.581	Remote Similarity	NPD6013	Approved
0.58	Remote Similarity	NPD5285	Approved
0.58	Remote Similarity	NPD4696	Approved
0.58	Remote Similarity	NPD5286	Approved
0.5789	Remote Similarity	NPD287	Approved
0.5769	Remote Similarity	NPD368	Approved
0.5769	Remote Similarity	NPD5701	Approved
0.5758	Remote Similarity	NPD4755	Approved
0.5755	Remote Similarity	NPD7102	Approved
0.5755	Remote Similarity	NPD7290	Approved
0.5755	Remote Similarity	NPD6883	Approved
0.5743	Remote Similarity	NPD5223	Approved
0.5732	Remote Similarity	NPD3621	Clinical (unspecified phase)
0.5729	Remote Similarity	NPD6411	Approved
0.5729	Remote Similarity	NPD7637	Suspended
0.5729	Remote Similarity	NPD4810	Clinical (unspecified phase)
0.5727	Remote Similarity	NPD7115	Discovery
0.5714	Remote Similarity	NPD7320	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