NPASS Compound

Structure

NPC471498 OpenBabel07101718322D 31 31 0 0 0 0 0 0 0 0999 V2000 -8.6603 -8.0000 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 1.7321 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.7942 -7.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.7942 -6.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.6603 -6.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.6603 -5.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.5263 -4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.5263 -3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.6603 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.6603 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.7942 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9282 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 -1.5000 0.0000 C 0 0 0 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 -4.3301 -1.5000 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 -2.5981 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 C 0 0 0 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 0.8660 2.5000 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 1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 4 1 0 0 0 0 2 23 1 0 0 0 0 3 24 1 0 0 0 0 4 5 1 0 0 0 0 5 6 1 0 0 0 0 6 7 1 0 0 0 0 7 8 1 0 0 0 0 8 9 2 0 0 0 0 9 10 1 0 0 0 0 10 11 1 0 0 0 0 11 12 2 0 0 0 0 12 13 1 0 0 0 0 13 14 1 0 0 0 0 14 15 1 0 0 0 0 15 16 1 0 0 0 0 16 17 1 0 0 0 0 17 18 1 0 0 0 0 18 19 1 0 0 0 0 19 25 1 0 0 0 0 20 25 2 0 0 0 0 20 26 1 0 0 0 0 21 25 1 0 0 0 0 21 27 2 0 0 0 0 22 26 2 0 0 0 0 22 27 1 0 0 0 0 23 28 2 0 0 0 0 23 30 1 0 0 0 0 24 29 2 0 0 0 0 24 31 1 0 0 0 0 26 30 1 0 0 0 0 27 31 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	428.29
Volume:	483.697
LogP:	6.173
LogD:	4.268
LogS:	-2.748
# Rotatable Bonds:	18
TPSA:	52.6
# H-Bond Aceptor:	4
# H-Bond Donor:	0
# Rings:	1
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.118
Synthetic Accessibility Score:	2.615
Fsp3:	0.556
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
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:	-4.925
MDCK Permeability:	3.975829167757183e-05
Pgp-inhibitor:	0.004
Pgp-substrate:	0.003
Human Intestinal Absorption (HIA):	0.333
20% Bioavailability (F20%):	1.0
30% Bioavailability (F30%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.124
Plasma Protein Binding (PPB):	100.40306854248047%
Volume Distribution (VD):	1.063
Pgp-substrate:	0.9232096672058105%

ADMET: Metabolism

CYP1A2-inhibitor:	0.234
CYP1A2-substrate:	0.203
CYP2C19-inhibitor:	0.467
CYP2C19-substrate:	0.063
CYP2C9-inhibitor:	0.206
CYP2C9-substrate:	0.975
CYP2D6-inhibitor:	0.457
CYP2D6-substrate:	0.785
CYP3A4-inhibitor:	0.619
CYP3A4-substrate:	0.1

ADMET: Excretion

Clearance (CL):	2.87
Half-life (T1/2):	0.916

ADMET: Toxicity

hERG Blockers:	0.1
Human Hepatotoxicity (H-HT):	0.035
Drug-inuced Liver Injury (DILI):	0.176
AMES Toxicity:	0.194
Rat Oral Acute Toxicity:	0.05
Maximum Recommended Daily Dose:	0.797
Skin Sensitization:	0.976
Carcinogencity:	0.106
Eye Corrosion:	0.057
Eye Irritation:	0.671
Respiratory Toxicity:	0.911

Download Data

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

Natural Product: NPC471498

Natural Product ID:	NPC471498
*Common Name:**	Acetic Acid 3-Acetoxy-5-(Heptadeca-8,11-Dienyl)-Phenyl Ester
IUPAC Name:	[3-acetyloxy-5-[(8Z,11Z)-heptadeca-8,11-dienyl]phenyl] acetate
Synonyms:
Standard InCHIKey:	WXVTZFAQKBGMLT-MURFETPASA-N
Standard InCHI:	InChI=1S/C27H40O4/c1-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-25-20-26(30-23(2)28)22-27(21-25)31-24(3)29/h8-9,11-12,20-22H,4-7,10,13-19H2,1-3H3/b9-8-,12-11-
SMILES:	CCCCC/C=CC/C=CCCCCCCCc1cc(OC(=O)C)cc(c1)OC(=O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL253134
PubChem CID:	23626631
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0002319] Phenol esters

*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
NPO5292	Stylogyne turbacensis	Species	Primulaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17629327]
NPO5292	Stylogyne turbacensis	Species	Primulaceae	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	2

Activity Type	# Activity
Cell Line	1
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT189	Cell Line	Vero	Chlorocebus aethiops	IC50	=	124000.0	nM	PMID[450231]
NPT580	Organism	Trypanosoma cruzi	Trypanosoma cruzi	IC50	=	117000.0	nM	PMID[450231]

☑ 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 NPC471498 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	311
0.1-0.2	1572
0.2-0.3	4849
0.3-0.4	12722
0.4-0.5	5531
0.5-0.6	6093
0.6-0.7	9257
0.7-0.8	2243
0.8-0.85	92
0.85-0.9	18
0.9-0.95	5
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC471503
0.9732	High Similarity	NPC471504
0.9732	High Similarity	NPC473290
0.9316	High Similarity	NPC140521
0.9237	High Similarity	NPC249836
0.9153	High Similarity	NPC78446
0.8926	High Similarity	NPC474821
0.8926	High Similarity	NPC474670
0.8852	High Similarity	NPC474636
0.8843	High Similarity	NPC474632
0.871	High Similarity	NPC474617
0.8699	High Similarity	NPC474616
0.8689	High Similarity	NPC101894
0.8678	High Similarity	NPC73413
0.8678	High Similarity	NPC201667
0.8673	High Similarity	NPC2682
0.864	High Similarity	NPC142530
0.8607	High Similarity	NPC471828
0.8607	High Similarity	NPC471827
0.8595	High Similarity	NPC472518
0.8595	High Similarity	NPC109675
0.8595	High Similarity	NPC273772
0.8595	High Similarity	NPC315807
0.8571	High Similarity	NPC474635
0.856	High Similarity	NPC79184
0.856	High Similarity	NPC307042
0.8559	High Similarity	NPC96705
0.8559	High Similarity	NPC152306
0.8548	High Similarity	NPC210674
0.8548	High Similarity	NPC474651
0.8548	High Similarity	NPC474623
0.8547	High Similarity	NPC123559
0.8547	High Similarity	NPC128633
0.8537	High Similarity	NPC127604
0.8525	High Similarity	NPC27671
0.8522	High Similarity	NPC280760
0.8512	High Similarity	NPC248429
0.8512	High Similarity	NPC96286
0.8509	High Similarity	NPC25067
0.8509	High Similarity	NPC88868
0.8509	High Similarity	NPC231251
0.8504	High Similarity	NPC474810
0.85	High Similarity	NPC235190
0.85	High Similarity	NPC163200
0.85	High Similarity	NPC180006
0.8496	Intermediate Similarity	NPC291837
0.8496	Intermediate Similarity	NPC245115
0.8487	Intermediate Similarity	NPC298796
0.8475	Intermediate Similarity	NPC127894
0.8475	Intermediate Similarity	NPC219070
0.8475	Intermediate Similarity	NPC15860
0.8475	Intermediate Similarity	NPC470759
0.8468	Intermediate Similarity	NPC194841
0.8413	Intermediate Similarity	NPC476399
0.8413	Intermediate Similarity	NPC19242
0.8407	Intermediate Similarity	NPC35543
0.8403	Intermediate Similarity	NPC265547
0.84	Intermediate Similarity	NPC472519
0.84	Intermediate Similarity	NPC185066
0.839	Intermediate Similarity	NPC114064
0.8387	Intermediate Similarity	NPC471826
0.8385	Intermediate Similarity	NPC476171
0.8385	Intermediate Similarity	NPC474530
0.8385	Intermediate Similarity	NPC474521
0.8385	Intermediate Similarity	NPC474540
0.8374	Intermediate Similarity	NPC111347
0.8374	Intermediate Similarity	NPC291899
0.8372	Intermediate Similarity	NPC224941
0.8372	Intermediate Similarity	NPC252095
0.8372	Intermediate Similarity	NPC311430
0.8361	Intermediate Similarity	NPC288238
0.8348	Intermediate Similarity	NPC303521
0.8348	Intermediate Similarity	NPC168657
0.8347	Intermediate Similarity	NPC472596
0.8347	Intermediate Similarity	NPC218753
0.8347	Intermediate Similarity	NPC267064
0.8346	Intermediate Similarity	NPC147317
0.8333	Intermediate Similarity	NPC98748
0.8333	Intermediate Similarity	NPC281356
0.8333	Intermediate Similarity	NPC168710
0.832	Intermediate Similarity	NPC243688
0.8308	Intermediate Similarity	NPC286843
0.8305	Intermediate Similarity	NPC53906
0.8295	Intermediate Similarity	NPC474600
0.8295	Intermediate Similarity	NPC309744
0.8288	Intermediate Similarity	NPC307425
0.8281	Intermediate Similarity	NPC319969
0.8281	Intermediate Similarity	NPC14248
0.8279	Intermediate Similarity	NPC144418
0.8279	Intermediate Similarity	NPC187868
0.8279	Intermediate Similarity	NPC52247
0.8268	Intermediate Similarity	NPC80170
0.8268	Intermediate Similarity	NPC32463
0.8264	Intermediate Similarity	NPC222175
0.8261	Intermediate Similarity	NPC82016
0.8254	Intermediate Similarity	NPC469453
0.8254	Intermediate Similarity	NPC199204
0.8244	Intermediate Similarity	NPC306365
0.824	Intermediate Similarity	NPC188327
0.824	Intermediate Similarity	NPC234109
0.8231	Intermediate Similarity	NPC234865
0.823	Intermediate Similarity	NPC473393
0.823	Intermediate Similarity	NPC473855
0.822	Intermediate Similarity	NPC276737
0.822	Intermediate Similarity	NPC22610
0.8217	Intermediate Similarity	NPC7526
0.8217	Intermediate Similarity	NPC241341
0.8217	Intermediate Similarity	NPC167111
0.8217	Intermediate Similarity	NPC296624
0.8217	Intermediate Similarity	NPC318400
0.8217	Intermediate Similarity	NPC36437
0.8217	Intermediate Similarity	NPC233018
0.8217	Intermediate Similarity	NPC207002
0.8217	Intermediate Similarity	NPC133956
0.8217	Intermediate Similarity	NPC471910
0.8217	Intermediate Similarity	NPC31849
0.8217	Intermediate Similarity	NPC222036
0.8211	Intermediate Similarity	NPC261661
0.8211	Intermediate Similarity	NPC257188
0.8211	Intermediate Similarity	NPC13007
0.8203	Intermediate Similarity	NPC272650
0.8203	Intermediate Similarity	NPC267336
0.8198	Intermediate Similarity	NPC107101
0.8197	Intermediate Similarity	NPC322569
0.8182	Intermediate Similarity	NPC137294
0.8182	Intermediate Similarity	NPC475961
0.8182	Intermediate Similarity	NPC59561
0.8182	Intermediate Similarity	NPC254625
0.8182	Intermediate Similarity	NPC470161
0.8182	Intermediate Similarity	NPC172253
0.8182	Intermediate Similarity	NPC85895
0.8175	Intermediate Similarity	NPC258567
0.8175	Intermediate Similarity	NPC224774
0.8175	Intermediate Similarity	NPC121740
0.8168	Intermediate Similarity	NPC471719
0.8167	Intermediate Similarity	NPC33270
0.8167	Intermediate Similarity	NPC69261
0.8167	Intermediate Similarity	NPC474933
0.816	Intermediate Similarity	NPC93219
0.816	Intermediate Similarity	NPC170749
0.816	Intermediate Similarity	NPC244495
0.816	Intermediate Similarity	NPC168259
0.8154	Intermediate Similarity	NPC267412
0.8154	Intermediate Similarity	NPC100986
0.8154	Intermediate Similarity	NPC166672
0.8154	Intermediate Similarity	NPC47163
0.8154	Intermediate Similarity	NPC84894
0.8154	Intermediate Similarity	NPC198381
0.8154	Intermediate Similarity	NPC195343
0.8154	Intermediate Similarity	NPC319859
0.8154	Intermediate Similarity	NPC287182
0.8154	Intermediate Similarity	NPC74655
0.8154	Intermediate Similarity	NPC164269
0.8154	Intermediate Similarity	NPC127888
0.8154	Intermediate Similarity	NPC55149
0.8154	Intermediate Similarity	NPC18804
0.8154	Intermediate Similarity	NPC260265
0.8154	Intermediate Similarity	NPC307412
0.8154	Intermediate Similarity	NPC131950
0.8145	Intermediate Similarity	NPC279379
0.8145	Intermediate Similarity	NPC290605
0.8145	Intermediate Similarity	NPC154176
0.8145	Intermediate Similarity	NPC173350
0.8145	Intermediate Similarity	NPC108545
0.8145	Intermediate Similarity	NPC50720
0.8142	Intermediate Similarity	NPC283546
0.814	Intermediate Similarity	NPC137669
0.814	Intermediate Similarity	NPC19157
0.814	Intermediate Similarity	NPC245120
0.814	Intermediate Similarity	NPC5423
0.8136	Intermediate Similarity	NPC303522
0.8136	Intermediate Similarity	NPC204120
0.813	Intermediate Similarity	NPC477886
0.8125	Intermediate Similarity	NPC244799
0.8125	Intermediate Similarity	NPC240722
0.8125	Intermediate Similarity	NPC113098
0.812	Intermediate Similarity	NPC255068
0.811	Intermediate Similarity	NPC157212
0.8106	Intermediate Similarity	NPC14697
0.8106	Intermediate Similarity	NPC474886
0.8106	Intermediate Similarity	NPC131198
0.8106	Intermediate Similarity	NPC105493
0.8099	Intermediate Similarity	NPC474612
0.8095	Intermediate Similarity	NPC329272
0.8095	Intermediate Similarity	NPC163248
0.8092	Intermediate Similarity	NPC472424
0.8092	Intermediate Similarity	NPC281241
0.8092	Intermediate Similarity	NPC471909
0.8092	Intermediate Similarity	NPC86892
0.8092	Intermediate Similarity	NPC471625
0.8092	Intermediate Similarity	NPC469675
0.8083	Intermediate Similarity	NPC141090
0.8083	Intermediate Similarity	NPC150624
0.8077	Intermediate Similarity	NPC469449
0.8077	Intermediate Similarity	NPC54503
0.8077	Intermediate Similarity	NPC472522
0.8077	Intermediate Similarity	NPC472524
0.8077	Intermediate Similarity	NPC55147
0.807	Intermediate Similarity	NPC238115
0.8067	Intermediate Similarity	NPC235250

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 NPC471498 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	292
0.1-0.2	1001
0.2-0.3	1714
0.3-0.4	2702
0.4-0.5	1763
0.5-0.6	1057
0.6-0.7	539
0.7-0.8	81
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8362	Intermediate Similarity	NPD5535	Approved
0.8279	Intermediate Similarity	NPD422	Phase 1
0.8125	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.8115	Intermediate Similarity	NPD17	Approved
0.8	Intermediate Similarity	NPD4749	Approved
0.7969	Intermediate Similarity	NPD1008	Clinical (unspecified phase)
0.792	Intermediate Similarity	NPD1608	Approved
0.7903	Intermediate Similarity	NPD3496	Discontinued
0.7868	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7846	Intermediate Similarity	NPD1296	Phase 2
0.784	Intermediate Similarity	NPD1611	Approved
0.7823	Intermediate Similarity	NPD1778	Approved
0.7769	Intermediate Similarity	NPD4625	Phase 3
0.7759	Intermediate Similarity	NPD9697	Approved
0.7742	Intermediate Similarity	NPD5691	Approved
0.7742	Intermediate Similarity	NPD5585	Approved
0.771	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7705	Intermediate Similarity	NPD6671	Approved
0.7698	Intermediate Similarity	NPD7837	Clinical (unspecified phase)
0.7692	Intermediate Similarity	NPD4908	Phase 1
0.7692	Intermediate Similarity	NPD3134	Approved
0.7669	Intermediate Similarity	NPD5124	Phase 1
0.7669	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7634	Intermediate Similarity	NPD7095	Approved
0.763	Intermediate Similarity	NPD3748	Approved
0.7627	Intermediate Similarity	NPD1358	Approved
0.7603	Intermediate Similarity	NPD7843	Approved
0.7597	Intermediate Similarity	NPD2797	Approved
0.7597	Intermediate Similarity	NPD3267	Approved
0.7597	Intermediate Similarity	NPD3266	Approved
0.7576	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7574	Intermediate Similarity	NPD6100	Approved
0.7574	Intermediate Similarity	NPD6099	Approved
0.7563	Intermediate Similarity	NPD2684	Approved
0.7561	Intermediate Similarity	NPD7157	Approved
0.7559	Intermediate Similarity	NPD1610	Phase 2
0.7557	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7557	Intermediate Similarity	NPD6832	Phase 2
0.754	Intermediate Similarity	NPD4626	Approved
0.7538	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.752	Intermediate Similarity	NPD1548	Phase 1
0.7519	Intermediate Similarity	NPD3225	Approved
0.7519	Intermediate Similarity	NPD8032	Phase 2
0.75	Intermediate Similarity	NPD2981	Phase 2
0.75	Intermediate Similarity	NPD3027	Phase 3
0.7481	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7481	Intermediate Similarity	NPD2237	Approved
0.7444	Intermediate Similarity	NPD3268	Approved
0.7442	Intermediate Similarity	NPD2982	Phase 2
0.7442	Intermediate Similarity	NPD4359	Approved
0.7442	Intermediate Similarity	NPD2983	Phase 2
0.744	Intermediate Similarity	NPD7644	Approved
0.741	Intermediate Similarity	NPD1652	Phase 2
0.7398	Intermediate Similarity	NPD5283	Phase 1
0.7391	Intermediate Similarity	NPD5762	Approved
0.7391	Intermediate Similarity	NPD5763	Approved
0.7364	Intermediate Similarity	NPD9717	Approved
0.7357	Intermediate Similarity	NPD3750	Approved
0.7353	Intermediate Similarity	NPD6653	Approved
0.7348	Intermediate Similarity	NPD3018	Phase 2
0.7347	Intermediate Similarity	NPD7819	Suspended
0.7343	Intermediate Similarity	NPD1940	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD4307	Phase 2
0.7333	Intermediate Similarity	NPD1613	Approved
0.7333	Intermediate Similarity	NPD4060	Phase 1
0.7333	Intermediate Similarity	NPD4140	Approved
0.7319	Intermediate Similarity	NPD2796	Approved
0.731	Intermediate Similarity	NPD8158	Clinical (unspecified phase)
0.7287	Intermediate Similarity	NPD3705	Approved
0.7286	Intermediate Similarity	NPD1243	Approved
0.7279	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7252	Intermediate Similarity	NPD6696	Suspended
0.7246	Intermediate Similarity	NPD7033	Discontinued
0.7226	Intermediate Similarity	NPD2653	Approved
0.7222	Intermediate Similarity	NPD7314	Clinical (unspecified phase)
0.7214	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7213	Intermediate Similarity	NPD4750	Phase 3
0.7209	Intermediate Similarity	NPD3847	Discontinued
0.7203	Intermediate Similarity	NPD940	Approved
0.7203	Intermediate Similarity	NPD846	Approved
0.7203	Intermediate Similarity	NPD6799	Approved
0.7197	Intermediate Similarity	NPD6362	Approved
0.7194	Intermediate Similarity	NPD1551	Phase 2
0.719	Intermediate Similarity	NPD290	Approved
0.7185	Intermediate Similarity	NPD411	Approved
0.7176	Intermediate Similarity	NPD5327	Phase 3
0.7172	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7164	Intermediate Similarity	NPD2614	Approved
0.7154	Intermediate Similarity	NPD1281	Approved
0.7154	Intermediate Similarity	NPD1091	Approved
0.7153	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7153	Intermediate Similarity	NPD6355	Discontinued
0.7153	Intermediate Similarity	NPD447	Suspended
0.7143	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD6002	Phase 3
0.7143	Intermediate Similarity	NPD6005	Phase 3
0.7143	Intermediate Similarity	NPD6004	Phase 3
0.7143	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD1019	Discontinued
0.7132	Intermediate Similarity	NPD2107	Clinical (unspecified phase)
0.7132	Intermediate Similarity	NPD2423	Clinical (unspecified phase)
0.7132	Intermediate Similarity	NPD4870	Approved
0.7123	Intermediate Similarity	NPD1653	Approved
0.7122	Intermediate Similarity	NPD4308	Phase 3
0.7121	Intermediate Similarity	NPD8651	Approved
0.712	Intermediate Similarity	NPD1241	Discontinued
0.7114	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7113	Intermediate Similarity	NPD3892	Phase 2
0.7109	Intermediate Similarity	NPD1894	Discontinued
0.7095	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.709	Intermediate Similarity	NPD2861	Phase 2
0.708	Intermediate Similarity	NPD2979	Phase 3
0.7073	Intermediate Similarity	NPD5451	Approved
0.7071	Intermediate Similarity	NPD6032	Approved
0.7068	Intermediate Similarity	NPD1203	Approved
0.7068	Intermediate Similarity	NPD987	Approved
0.7067	Intermediate Similarity	NPD3817	Phase 2
0.7059	Intermediate Similarity	NPD1699	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD6798	Discontinued
0.7055	Intermediate Similarity	NPD920	Approved
0.7054	Intermediate Similarity	NPD1651	Approved
0.705	Intermediate Similarity	NPD6111	Discontinued
0.705	Intermediate Similarity	NPD2200	Suspended
0.704	Intermediate Similarity	NPD821	Approved
0.7034	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7031	Intermediate Similarity	NPD5536	Phase 2
0.7029	Intermediate Similarity	NPD4340	Discontinued
0.7027	Intermediate Similarity	NPD6599	Discontinued
0.7023	Intermediate Similarity	NPD1535	Discovery
0.702	Intermediate Similarity	NPD7768	Phase 2
0.7014	Intermediate Similarity	NPD6667	Approved
0.7014	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7014	Intermediate Similarity	NPD6666	Approved
0.7013	Intermediate Similarity	NPD7229	Phase 3
0.7008	Intermediate Similarity	NPD2557	Approved
0.7008	Intermediate Similarity	NPD6387	Discontinued
0.7007	Intermediate Similarity	NPD6233	Phase 2
0.6993	Remote Similarity	NPD7466	Approved
0.6993	Remote Similarity	NPD4628	Phase 3
0.6993	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.6992	Remote Similarity	NPD1283	Approved
0.6985	Remote Similarity	NPD5746	Approved
0.698	Remote Similarity	NPD7411	Suspended
0.6975	Remote Similarity	NPD1242	Phase 1
0.6974	Remote Similarity	NPD7075	Discontinued
0.6974	Remote Similarity	NPD6971	Discontinued
0.697	Remote Similarity	NPD1481	Phase 2
0.6967	Remote Similarity	NPD968	Approved
0.696	Remote Similarity	NPD1137	Approved
0.696	Remote Similarity	NPD228	Approved
0.696	Remote Similarity	NPD1139	Approved
0.6954	Remote Similarity	NPD5402	Approved
0.6953	Remote Similarity	NPD3596	Phase 2
0.695	Remote Similarity	NPD2438	Suspended
0.695	Remote Similarity	NPD2935	Discontinued
0.6948	Remote Similarity	NPD7199	Phase 2
0.6944	Remote Similarity	NPD5307	Clinical (unspecified phase)
0.6939	Remote Similarity	NPD5403	Approved
0.6934	Remote Similarity	NPD1048	Approved
0.6929	Remote Similarity	NPD7097	Phase 1
0.6928	Remote Similarity	NPD919	Approved
0.6923	Remote Similarity	NPD3445	Approved
0.6923	Remote Similarity	NPD3443	Approved
0.6923	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD3444	Approved
0.6923	Remote Similarity	NPD6830	Clinical (unspecified phase)
0.6918	Remote Similarity	NPD5401	Approved
0.6918	Remote Similarity	NPD3146	Approved
0.6918	Remote Similarity	NPD7447	Phase 1
0.6918	Remote Similarity	NPD2533	Approved
0.6918	Remote Similarity	NPD3688	Clinical (unspecified phase)
0.6918	Remote Similarity	NPD642	Clinical (unspecified phase)
0.6918	Remote Similarity	NPD3157	Approved
0.6918	Remote Similarity	NPD2532	Approved
0.6918	Remote Similarity	NPD2534	Approved
0.6918	Remote Similarity	NPD3158	Phase 1
0.6917	Remote Similarity	NPD3685	Discontinued
0.6917	Remote Similarity	NPD1420	Approved
0.6917	Remote Similarity	NPD1421	Approved
0.6908	Remote Similarity	NPD4868	Clinical (unspecified phase)
0.6906	Remote Similarity	NPD230	Phase 1
0.6905	Remote Similarity	NPD1138	Approved
0.6901	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.6901	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6897	Remote Similarity	NPD7124	Phase 2
0.6892	Remote Similarity	NPD3686	Approved
0.6892	Remote Similarity	NPD3687	Approved
0.6889	Remote Similarity	NPD6584	Phase 3
0.6887	Remote Similarity	NPD2393	Clinical (unspecified phase)
0.6884	Remote Similarity	NPD5745	Approved
0.6884	Remote Similarity	NPD4062	Phase 3
0.6879	Remote Similarity	NPD2799	Discontinued
0.6875	Remote Similarity	NPD4110	Phase 3
0.6875	Remote Similarity	NPD4109	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD709	Approved
0.6861	Remote Similarity	NPD2598	Clinical (unspecified phase)
0.6861	Remote Similarity	NPD5163	Phase 2
0.6859	Remote Similarity	NPD7184	Clinical (unspecified phase)
0.6853	Remote Similarity	NPD1549	Phase 2

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