NPASS Compound

Structure

CID188291 OpenBabel06191715572D 38 45 0 0 1 0 0 0 0 0999 V2000 0.2025 -0.9396 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4261 0.0906 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8818 1.9329 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1793 -1.8807 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5228 -1.6487 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0868 0.1655 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8200 0.8087 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3650 -1.6602 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7669 -0.5231 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2029 0.6928 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5861 -1.1887 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7085 -1.4282 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8942 -1.2077 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.9247 -0.5116 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.3955 -0.9641 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.9375 -0.5800 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.1104 -0.2911 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9376 1.1170 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.5319 0.2683 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8833 -0.3403 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6726 -0.1557 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0286 1.8831 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2027 -0.1558 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.5812 -0.7436 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.2029 1.5411 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.2261 1.1721 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.7014 -1.0192 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.5319 1.1170 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.6942 -1.4904 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.9552 0.5431 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7245 -0.2296 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.3514 -0.5476 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.6231 2.4885 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.8312 0.5774 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0927 -1.3706 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.6724 0.6927 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.3141 2.0677 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3 25 1 0 0 0 0 4 5 1 0 0 0 0 4 12 2 0 0 0 0 5 15 1 0 0 0 0 6 7 1 0 0 0 0 6 14 1 0 0 0 0 7 26 1 0 0 0 0 8 12 1 0 0 0 0 8 13 1 0 0 0 0 9 13 1 0 0 0 0 9 17 1 0 0 0 0 10 18 1 0 0 0 0 10 23 1 0 0 0 0 11 16 1 0 0 0 0 11 35 1 0 0 0 0 12 24 1 0 0 0 0 13 29 1 6 0 0 0 14 15 1 0 0 0 0 14 24 1 1 0 0 0 15 27 1 6 0 0 0 16 21 1 0 0 0 0 16 23 1 6 0 0 0 17 24 1 0 0 0 0 17 30 2 0 0 0 0 18 25 1 6 0 0 0 18 36 1 0 0 0 0 19 20 1 0 0 0 0 19 23 1 6 0 0 0 19 28 1 0 0 0 0 20 31 2 0 0 0 0 21 32 2 0 0 0 0 21 36 1 0 0 0 0 22 26 1 0 0 0 0 22 33 2 0 0 0 0 22 37 1 0 0 0 0 23 1 1 1 0 0 0 24 2 1 1 0 0 0 25 28 1 6 0 0 0 25 37 1 0 0 0 0 26 28 1 6 0 0 0 26 34 1 0 0 0 0 27 20 1 1 0 0 0 27 35 1 0 0 0 0 27 38 1 0 0 0 0 28 38 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	528.2
Volume:	499.112
LogP:	1.939
LogD:	1.323
LogS:	-4.691
# Rotatable Bonds:	0
TPSA:	145.66
# H-Bond Aceptor:	10
# H-Bond Donor:	2
# Rings:	8
# Heavy Atoms:	10

MedChem Properties

QED Drug-Likeness Score:	0.341
Synthetic Accessibility Score:	7.535
Fsp3:	0.786
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.413
MDCK Permeability:	2.0508459783741273e-05
Pgp-inhibitor:	0.344
Pgp-substrate:	0.98
Human Intestinal Absorption (HIA):	0.086
20% Bioavailability (F20%):	0.98
30% Bioavailability (F30%):	0.905

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.763
Plasma Protein Binding (PPB):	56.45319747924805%
Volume Distribution (VD):	0.527
Pgp-substrate:	47.83656692504883%

ADMET: Metabolism

CYP1A2-inhibitor:	0.003
CYP1A2-substrate:	0.979
CYP2C19-inhibitor:	0.022
CYP2C19-substrate:	0.761
CYP2C9-inhibitor:	0.012
CYP2C9-substrate:	0.002
CYP2D6-inhibitor:	0.001
CYP2D6-substrate:	0.071
CYP3A4-inhibitor:	0.673
CYP3A4-substrate:	0.796

ADMET: Excretion

Clearance (CL):	6.969
Half-life (T1/2):	0.273

ADMET: Toxicity

hERG Blockers:	0.006
Human Hepatotoxicity (H-HT):	0.052
Drug-inuced Liver Injury (DILI):	0.413
AMES Toxicity:	0.197
Rat Oral Acute Toxicity:	0.997
Maximum Recommended Daily Dose:	0.909
Skin Sensitization:	0.051
Carcinogencity:	0.956
Eye Corrosion:	0.004
Eye Irritation:	0.018
Respiratory Toxicity:	0.946

Download Data

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

Natural Product: NPC188291

Natural Product ID:	NPC188291
*Common Name:**	Physalin Y
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	AMFDIHDGEZLBRP-INTHQURXSA-N
Standard InCHI:	InChI=1S/C28H32O10/c1-23-10-18-25(3)28-19(23)20(31)27(38-28,35-11-16(23)21(32)36-18)15-5-4-12-8-13(29)9-17(30)24(12,2)14(15)6-7-26(28,34)22(33)37-25/h4,13-16,18-19,29,34H,5-11H2,1-3H3/t13-,14-,15+,16-,18+,19-,23+,24-,25-,26-,27+,28-/m0/s1
SMILES:	O[C@@H]1CC(=O)[C@]2(C(=CC[C@@H]3[C@@H]2CC[C@]2(O)C(=O)O[C@@]4([C@@]52O[C@@]23OC[C@@H]3[C@@]([C@@H]5C2=O)(C)C[C@H]4OC3=O)C)C1)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL503428
PubChem CID:	44577483
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0001671] Physalins and derivatives

*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
NPO14304.1	Physalis alkekengi var. franchetii	Varieties	Solanaceae	Eukaryota	calyces	Yilan, Heilongjiang Province, China	2004-SEP	PMID[18348534]
NPO14304.1	Physalis alkekengi var. franchetii	Varieties	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO14304	Physalis alkekengi	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO14304	Physalis alkekengi	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO14304.1	Physalis alkekengi var. franchetii	Varieties	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO14304	Physalis alkekengi	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO14304	Physalis alkekengi	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
IC50	1

Activity Type	# Activity
Cell Line	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT113	Cell Line	RAW264.7	Mus musculus	IC50	=	79230.0	nM	PMID[553373]

☑ 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 NPC188291 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	318
0.1-0.2	1935
0.2-0.3	5720
0.3-0.4	10017
0.4-0.5	11406
0.5-0.6	6969
0.6-0.7	4677
0.7-0.8	1547
0.8-0.85	85
0.85-0.9	11
0.9-0.95	9
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9587	High Similarity	NPC100390
0.9587	High Similarity	NPC254614
0.9274	High Similarity	NPC15215
0.9274	High Similarity	NPC242486
0.9268	High Similarity	NPC254146
0.9268	High Similarity	NPC6274
0.9268	High Similarity	NPC33378
0.9262	High Similarity	NPC264192
0.9127	High Similarity	NPC243014
0.896	High Similarity	NPC102316
0.8908	High Similarity	NPC297179
0.8908	High Similarity	NPC17772
0.875	High Similarity	NPC204552
0.875	High Similarity	NPC470776
0.875	High Similarity	NPC188667
0.874	High Similarity	NPC168879
0.8739	High Similarity	NPC134869
0.8739	High Similarity	NPC152199
0.8739	High Similarity	NPC40632
0.8739	High Similarity	NPC328374
0.8739	High Similarity	NPC96312
0.8739	High Similarity	NPC251236
0.8739	High Similarity	NPC235539
0.8689	High Similarity	NPC477046
0.8689	High Similarity	NPC102822
0.8678	High Similarity	NPC470777
0.8667	High Similarity	NPC470854
0.8667	High Similarity	NPC287343
0.8667	High Similarity	NPC474654
0.8667	High Similarity	NPC97908
0.8667	High Similarity	NPC122033
0.8655	High Similarity	NPC18547
0.8655	High Similarity	NPC473798
0.8655	High Similarity	NPC474906
0.8607	High Similarity	NPC112038
0.8583	High Similarity	NPC16081
0.8583	High Similarity	NPC173686
0.8583	High Similarity	NPC474734
0.8583	High Similarity	NPC470628
0.8583	High Similarity	NPC259306
0.8583	High Similarity	NPC207217
0.8583	High Similarity	NPC474046
0.8571	High Similarity	NPC49451
0.8548	High Similarity	NPC91693
0.8548	High Similarity	NPC67251
0.8548	High Similarity	NPC18945
0.8548	High Similarity	NPC105926
0.8548	High Similarity	NPC265557
0.8525	High Similarity	NPC469488
0.8512	High Similarity	NPC176513
0.8512	High Similarity	NPC470775
0.8512	High Similarity	NPC473590
0.85	High Similarity	NPC470919
0.85	High Similarity	NPC143268
0.85	High Similarity	NPC323821
0.85	High Similarity	NPC45218
0.85	High Similarity	NPC469877
0.85	High Similarity	NPC268238
0.8492	Intermediate Similarity	NPC470780
0.8487	Intermediate Similarity	NPC474516
0.8487	Intermediate Similarity	NPC289312
0.8487	Intermediate Similarity	NPC11252
0.848	Intermediate Similarity	NPC470922
0.848	Intermediate Similarity	NPC476729
0.848	Intermediate Similarity	NPC24651
0.8468	Intermediate Similarity	NPC312833
0.8425	Intermediate Similarity	NPC295220
0.8425	Intermediate Similarity	NPC475636
0.8417	Intermediate Similarity	NPC7921
0.8417	Intermediate Similarity	NPC208998
0.8413	Intermediate Similarity	NPC181999
0.8413	Intermediate Similarity	NPC87662
0.8403	Intermediate Similarity	NPC201992
0.84	Intermediate Similarity	NPC478066
0.8387	Intermediate Similarity	NPC470779
0.8387	Intermediate Similarity	NPC75417
0.8359	Intermediate Similarity	NPC309096
0.8359	Intermediate Similarity	NPC54614
0.8347	Intermediate Similarity	NPC117712
0.8333	Intermediate Similarity	NPC302146
0.8333	Intermediate Similarity	NPC596
0.8333	Intermediate Similarity	NPC470477
0.8321	Intermediate Similarity	NPC262813
0.832	Intermediate Similarity	NPC40775
0.832	Intermediate Similarity	NPC235438
0.832	Intermediate Similarity	NPC249848
0.832	Intermediate Similarity	NPC107966
0.8306	Intermediate Similarity	NPC107338
0.8306	Intermediate Similarity	NPC109607
0.8293	Intermediate Similarity	NPC286347
0.8293	Intermediate Similarity	NPC251310
0.8268	Intermediate Similarity	NPC181066
0.8268	Intermediate Similarity	NPC469947
0.8268	Intermediate Similarity	NPC285091
0.8264	Intermediate Similarity	NPC51978
0.8258	Intermediate Similarity	NPC190065
0.8258	Intermediate Similarity	NPC251998
0.8258	Intermediate Similarity	NPC141215
0.8258	Intermediate Similarity	NPC471089
0.8254	Intermediate Similarity	NPC30735
0.8254	Intermediate Similarity	NPC235405
0.8254	Intermediate Similarity	NPC281148
0.8254	Intermediate Similarity	NPC227397
0.825	Intermediate Similarity	NPC171888
0.825	Intermediate Similarity	NPC146945
0.825	Intermediate Similarity	NPC157476
0.8226	Intermediate Similarity	NPC6377
0.8226	Intermediate Similarity	NPC114441
0.8226	Intermediate Similarity	NPC309780
0.8226	Intermediate Similarity	NPC472949
0.8226	Intermediate Similarity	NPC475171
0.8226	Intermediate Similarity	NPC180550
0.8226	Intermediate Similarity	NPC157868
0.8226	Intermediate Similarity	NPC208381
0.8226	Intermediate Similarity	NPC214484
0.8226	Intermediate Similarity	NPC475775
0.8226	Intermediate Similarity	NPC35405
0.8226	Intermediate Similarity	NPC469945
0.8226	Intermediate Similarity	NPC11551
0.8226	Intermediate Similarity	NPC473884
0.8226	Intermediate Similarity	NPC476529
0.8226	Intermediate Similarity	NPC39211
0.8211	Intermediate Similarity	NPC224121
0.8211	Intermediate Similarity	NPC309433
0.8203	Intermediate Similarity	NPC476008
0.8197	Intermediate Similarity	NPC243354
0.8195	Intermediate Similarity	NPC295885
0.8195	Intermediate Similarity	NPC140045
0.8189	Intermediate Similarity	NPC23275
0.8175	Intermediate Similarity	NPC162574
0.8175	Intermediate Similarity	NPC213952
0.8175	Intermediate Similarity	NPC471965
0.816	Intermediate Similarity	NPC294112
0.816	Intermediate Similarity	NPC471406
0.8151	Intermediate Similarity	NPC293850
0.8145	Intermediate Similarity	NPC318751
0.8134	Intermediate Similarity	NPC477232
0.8134	Intermediate Similarity	NPC477233
0.813	Intermediate Similarity	NPC213084
0.813	Intermediate Similarity	NPC190185
0.8125	Intermediate Similarity	NPC470218
0.8125	Intermediate Similarity	NPC174367
0.8125	Intermediate Similarity	NPC47113
0.8125	Intermediate Similarity	NPC477745
0.8115	Intermediate Similarity	NPC194273
0.811	Intermediate Similarity	NPC262199
0.811	Intermediate Similarity	NPC471964
0.811	Intermediate Similarity	NPC257211
0.811	Intermediate Similarity	NPC471961
0.811	Intermediate Similarity	NPC202666
0.811	Intermediate Similarity	NPC14617
0.8106	Intermediate Similarity	NPC478069
0.8099	Intermediate Similarity	NPC471243
0.8095	Intermediate Similarity	NPC11242
0.8095	Intermediate Similarity	NPC104372
0.8095	Intermediate Similarity	NPC223301
0.8095	Intermediate Similarity	NPC159309
0.8095	Intermediate Similarity	NPC297263
0.8095	Intermediate Similarity	NPC22956
0.8095	Intermediate Similarity	NPC86222
0.8095	Intermediate Similarity	NPC62725
0.8095	Intermediate Similarity	NPC275675
0.8095	Intermediate Similarity	NPC242840
0.8095	Intermediate Similarity	NPC301449
0.8095	Intermediate Similarity	NPC64715
0.8095	Intermediate Similarity	NPC114484
0.8095	Intermediate Similarity	NPC171544
0.8095	Intermediate Similarity	NPC222580
0.8095	Intermediate Similarity	NPC31193
0.8095	Intermediate Similarity	NPC31838
0.8083	Intermediate Similarity	NPC472534
0.8083	Intermediate Similarity	NPC143706
0.808	Intermediate Similarity	NPC319570
0.808	Intermediate Similarity	NPC268958
0.8077	Intermediate Similarity	NPC476851
0.8077	Intermediate Similarity	NPC476854
0.8067	Intermediate Similarity	NPC3316
0.8067	Intermediate Similarity	NPC293512
0.8067	Intermediate Similarity	NPC144854
0.8065	Intermediate Similarity	NPC470778
0.8065	Intermediate Similarity	NPC146432
0.8051	Intermediate Similarity	NPC475036
0.8049	Intermediate Similarity	NPC475633
0.8049	Intermediate Similarity	NPC299849
0.8047	Intermediate Similarity	NPC130229
0.8047	Intermediate Similarity	NPC30188
0.8047	Intermediate Similarity	NPC247315
0.8047	Intermediate Similarity	NPC177820
0.8047	Intermediate Similarity	NPC471963
0.8047	Intermediate Similarity	NPC33068
0.8047	Intermediate Similarity	NPC471962
0.8047	Intermediate Similarity	NPC473255
0.8031	Intermediate Similarity	NPC187290
0.8031	Intermediate Similarity	NPC21691
0.8031	Intermediate Similarity	NPC475591
0.8031	Intermediate Similarity	NPC10607
0.8031	Intermediate Similarity	NPC4749
0.8031	Intermediate Similarity	NPC236870
0.8031	Intermediate Similarity	NPC80986
0.8031	Intermediate Similarity	NPC275343

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 NPC188291 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	269
0.1-0.2	2161
0.2-0.3	4086
0.3-0.4	1704
0.4-0.5	507
0.5-0.6	255
0.6-0.7	142
0.7-0.8	26
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
0.811	Intermediate Similarity	NPD8328	Phase 3
0.8065	Intermediate Similarity	NPD8295	Clinical (unspecified phase)
0.7907	Intermediate Similarity	NPD7492	Approved
0.7874	Intermediate Similarity	NPD6059	Approved
0.7874	Intermediate Similarity	NPD6054	Approved
0.7863	Intermediate Similarity	NPD7736	Approved
0.7846	Intermediate Similarity	NPD6616	Approved
0.7786	Intermediate Similarity	NPD7078	Approved
0.7786	Intermediate Similarity	NPD8293	Discontinued
0.7752	Intermediate Similarity	NPD6370	Approved
0.7705	Intermediate Similarity	NPD5345	Clinical (unspecified phase)
0.7674	Intermediate Similarity	NPD6015	Approved
0.7674	Intermediate Similarity	NPD6016	Approved
0.7642	Intermediate Similarity	NPD8132	Clinical (unspecified phase)
0.7615	Intermediate Similarity	NPD5988	Approved
0.7597	Intermediate Similarity	NPD6319	Approved
0.7537	Intermediate Similarity	NPD7319	Approved
0.746	Intermediate Similarity	NPD6882	Approved
0.7364	Intermediate Similarity	NPD6009	Approved
0.736	Intermediate Similarity	NPD6373	Approved
0.736	Intermediate Similarity	NPD6372	Approved
0.7333	Intermediate Similarity	NPD6033	Approved
0.7323	Intermediate Similarity	NPD8297	Approved
0.7313	Intermediate Similarity	NPD7507	Approved
0.728	Intermediate Similarity	NPD7320	Approved
0.7273	Intermediate Similarity	NPD8515	Approved
0.7273	Intermediate Similarity	NPD8513	Phase 3
0.7273	Intermediate Similarity	NPD8516	Approved
0.7273	Intermediate Similarity	NPD8517	Approved
0.7258	Intermediate Similarity	NPD7128	Approved
0.7258	Intermediate Similarity	NPD6402	Approved
0.7258	Intermediate Similarity	NPD5739	Approved
0.7258	Intermediate Similarity	NPD6675	Approved
0.7244	Intermediate Similarity	NPD6650	Approved
0.7244	Intermediate Similarity	NPD6649	Approved
0.72	Intermediate Similarity	NPD6412	Phase 2
0.7143	Intermediate Similarity	NPD6899	Approved
0.7143	Intermediate Similarity	NPD6881	Approved
0.7143	Intermediate Similarity	NPD6921	Approved
0.7132	Intermediate Similarity	NPD4632	Approved
0.7063	Intermediate Similarity	NPD5697	Approved
0.7063	Intermediate Similarity	NPD5701	Approved
0.7031	Intermediate Similarity	NPD6883	Approved
0.7031	Intermediate Similarity	NPD7102	Approved
0.7031	Intermediate Similarity	NPD7290	Approved
0.7008	Intermediate Similarity	NPD6686	Approved
0.6992	Remote Similarity	NPD7516	Approved
0.6984	Remote Similarity	NPD6008	Approved
0.6977	Remote Similarity	NPD6869	Approved
0.6977	Remote Similarity	NPD8130	Phase 1
0.6977	Remote Similarity	NPD6617	Approved
0.6977	Remote Similarity	NPD6847	Approved
0.697	Remote Similarity	NPD7115	Discovery
0.6953	Remote Similarity	NPD6012	Approved
0.6953	Remote Similarity	NPD6013	Approved
0.6953	Remote Similarity	NPD6014	Approved
0.6917	Remote Similarity	NPD7328	Approved
0.6917	Remote Similarity	NPD7327	Approved
0.6912	Remote Similarity	NPD7604	Phase 2
0.6899	Remote Similarity	NPD4634	Approved
0.6889	Remote Similarity	NPD5983	Phase 2
0.6884	Remote Similarity	NPD8074	Phase 3
0.6875	Remote Similarity	NPD6011	Approved
0.687	Remote Similarity	NPD8133	Approved
0.6846	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6846	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6822	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6812	Remote Similarity	NPD6336	Discontinued
0.6777	Remote Similarity	NPD6399	Phase 3
0.6774	Remote Similarity	NPD5696	Approved
0.6769	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6765	Remote Similarity	NPD8379	Approved
0.6765	Remote Similarity	NPD8380	Approved
0.6765	Remote Similarity	NPD8335	Approved
0.6765	Remote Similarity	NPD8033	Approved
0.6765	Remote Similarity	NPD8378	Approved
0.6765	Remote Similarity	NPD8296	Approved
0.6694	Remote Similarity	NPD6411	Approved
0.6694	Remote Similarity	NPD6084	Phase 2
0.6694	Remote Similarity	NPD7902	Approved
0.6694	Remote Similarity	NPD4755	Approved
0.6694	Remote Similarity	NPD6083	Phase 2
0.6691	Remote Similarity	NPD8377	Approved
0.6691	Remote Similarity	NPD8294	Approved
0.6642	Remote Similarity	NPD6274	Approved
0.664	Remote Similarity	NPD4225	Approved
0.662	Remote Similarity	NPD5956	Approved
0.6618	Remote Similarity	NPD7101	Approved
0.6618	Remote Similarity	NPD7100	Approved
0.6587	Remote Similarity	NPD5285	Approved
0.6587	Remote Similarity	NPD4700	Approved
0.6587	Remote Similarity	NPD4696	Approved
0.6587	Remote Similarity	NPD5286	Approved
0.6585	Remote Similarity	NPD5282	Discontinued
0.6585	Remote Similarity	NPD7748	Approved
0.6557	Remote Similarity	NPD7515	Phase 2
0.6547	Remote Similarity	NPD6067	Discontinued
0.6544	Remote Similarity	NPD6335	Approved
0.6538	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6538	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6535	Remote Similarity	NPD1700	Approved
0.6529	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6529	Remote Similarity	NPD6101	Approved
0.6522	Remote Similarity	NPD6909	Approved
0.6522	Remote Similarity	NPD7503	Approved
0.6522	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.6522	Remote Similarity	NPD6908	Approved
0.6512	Remote Similarity	NPD8170	Clinical (unspecified phase)
0.6484	Remote Similarity	NPD4633	Approved
0.6484	Remote Similarity	NPD5211	Phase 2
0.6484	Remote Similarity	NPD5224	Approved
0.6484	Remote Similarity	NPD5225	Approved
0.6484	Remote Similarity	NPD5226	Approved
0.648	Remote Similarity	NPD4697	Phase 3
0.6471	Remote Similarity	NPD6317	Approved
0.6462	Remote Similarity	NPD4767	Approved
0.6462	Remote Similarity	NPD4768	Approved
0.6458	Remote Similarity	NPD7260	Phase 2
0.6452	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6452	Remote Similarity	NPD7900	Approved
0.6434	Remote Similarity	NPD5174	Approved
0.6434	Remote Similarity	NPD5175	Approved
0.6423	Remote Similarity	NPD6313	Approved
0.6423	Remote Similarity	NPD6314	Approved
0.6418	Remote Similarity	NPD6053	Discontinued
0.6414	Remote Similarity	NPD6845	Suspended
0.6406	Remote Similarity	NPD5223	Approved
0.64	Remote Similarity	NPD5695	Phase 3
0.6397	Remote Similarity	NPD6868	Approved
0.6393	Remote Similarity	NPD5328	Approved
0.6385	Remote Similarity	NPD5141	Approved
0.6378	Remote Similarity	NPD7638	Approved
0.6371	Remote Similarity	NPD5778	Approved
0.6371	Remote Similarity	NPD5779	Approved
0.6364	Remote Similarity	NPD4730	Approved
0.6364	Remote Similarity	NPD4729	Approved
0.6364	Remote Similarity	NPD3573	Approved
0.6351	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.6349	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6349	Remote Similarity	NPD5222	Approved
0.6349	Remote Similarity	NPD5221	Approved
0.6328	Remote Similarity	NPD7640	Approved
0.6328	Remote Similarity	NPD7639	Approved
0.6311	Remote Similarity	NPD6672	Approved
0.6311	Remote Similarity	NPD5737	Approved
0.6308	Remote Similarity	NPD4754	Approved
0.6301	Remote Similarity	NPD8338	Approved
0.6299	Remote Similarity	NPD5173	Approved
0.629	Remote Similarity	NPD7983	Approved
0.629	Remote Similarity	NPD6079	Approved
0.629	Remote Similarity	NPD8035	Phase 2
0.629	Remote Similarity	NPD8034	Phase 2
0.6286	Remote Similarity	NPD8274	Clinical (unspecified phase)
0.6281	Remote Similarity	NPD3618	Phase 1
0.627	Remote Similarity	NPD4629	Approved
0.627	Remote Similarity	NPD5210	Approved
0.627	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.627	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6269	Remote Similarity	NPD5251	Approved
0.6269	Remote Similarity	NPD5250	Approved
0.6269	Remote Similarity	NPD5248	Approved
0.6269	Remote Similarity	NPD5247	Approved
0.6269	Remote Similarity	NPD5249	Phase 3
0.6269	Remote Similarity	NPD6371	Approved
0.625	Remote Similarity	NPD4786	Approved
0.6243	Remote Similarity	NPD8407	Phase 2
0.6241	Remote Similarity	NPD5128	Approved
0.6241	Remote Similarity	NPD8080	Discontinued
0.6218	Remote Similarity	NPD3667	Approved
0.6213	Remote Similarity	NPD7799	Discontinued
0.62	Remote Similarity	NPD6334	Approved
0.62	Remote Similarity	NPD6333	Approved
0.6174	Remote Similarity	NPD8387	Clinical (unspecified phase)
0.617	Remote Similarity	NPD8266	Approved
0.617	Remote Similarity	NPD8269	Approved
0.617	Remote Similarity	NPD8267	Approved
0.617	Remote Similarity	NPD8268	Approved
0.6163	Remote Similarity	NPD8368	Discontinued
0.6148	Remote Similarity	NPD6098	Approved
0.6138	Remote Similarity	NPD8337	Approved
0.6138	Remote Similarity	NPD8336	Approved
0.6136	Remote Similarity	NPD4056	Clinical (unspecified phase)
0.6136	Remote Similarity	NPD4057	Clinical (unspecified phase)
0.6129	Remote Similarity	NPD6673	Approved
0.6129	Remote Similarity	NPD6904	Approved
0.6129	Remote Similarity	NPD6080	Approved
0.6129	Remote Similarity	NPD4753	Phase 2
0.6111	Remote Similarity	NPD4202	Approved
0.6107	Remote Similarity	NPD8415	Approved
0.6103	Remote Similarity	NPD5215	Approved
0.6103	Remote Similarity	NPD5217	Approved
0.6103	Remote Similarity	NPD5216	Approved
0.608	Remote Similarity	NPD46	Approved
0.608	Remote Similarity	NPD6698	Approved
0.6066	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6048	Remote Similarity	NPD6903	Approved
0.6048	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6032	Remote Similarity	NPD7637	Suspended
0.6031	Remote Similarity	NPD5344	Discontinued
0.6029	Remote Similarity	NPD5135	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