NPASS Compound

Structure

CID102316 OpenBabel06191715442D 38 44 0 0 1 0 0 0 0 0999 V2000 -2.3239 -2.4307 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8396 -1.7239 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5193 1.0641 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9126 -1.0866 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5487 1.2071 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5487 0.5498 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9794 1.5358 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4184 0.7247 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2289 0.8388 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9794 -0.4362 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1036 -0.8769 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2037 -1.4091 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.9794 0.2211 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8409 0.2211 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.4102 -0.7648 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.4102 1.2071 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0826 -0.3787 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8409 -0.4362 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.2369 -1.1137 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.3460 -1.6280 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6196 -1.0991 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3162 0.9148 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7273 -1.2040 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.4102 0.5498 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.6799 -0.0846 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.7982 0.5102 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.4184 -0.9397 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.0230 -0.1075 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.4102 -1.7935 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.5193 1.7214 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.2385 -2.6510 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.5644 -1.5058 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.2803 1.9429 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0577 -0.0604 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.1483 -1.6645 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5590 -0.5839 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.8611 0.5473 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 1 12 1 0 0 0 0 4 25 1 0 0 0 0 5 6 1 0 0 0 0 5 7 2 0 0 0 0 6 13 1 0 0 0 0 7 16 1 0 0 0 0 8 9 1 0 0 0 0 8 14 1 0 0 0 0 9 26 1 0 0 0 0 10 13 2 0 0 0 0 10 15 1 0 0 0 0 11 17 1 0 0 0 0 11 23 1 0 0 0 0 12 21 1 0 0 0 0 12 23 1 6 0 0 0 13 24 1 0 0 0 0 14 18 1 0 0 0 0 14 24 1 6 0 0 0 15 18 1 0 0 0 0 15 29 1 1 0 0 0 16 24 1 0 0 0 0 16 30 2 0 0 0 0 17 25 1 1 0 0 0 17 36 1 0 0 0 0 18 27 1 1 0 0 0 19 20 1 0 0 0 0 19 23 1 1 0 0 0 19 28 1 0 0 0 0 20 27 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 2 1 6 0 0 0 24 3 1 6 0 0 0 25 28 1 6 0 0 0 25 37 1 0 0 0 0 26 28 1 1 0 0 0 26 34 1 0 0 0 0 27 35 1 1 0 0 0 27 38 1 0 0 0 0 28 38 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	528.2
Volume:	505.032
LogP:	1.242
LogD:	0.724
LogS:	-4.383
# Rotatable Bonds:	0
TPSA:	156.66
# H-Bond Aceptor:	10
# H-Bond Donor:	3
# Rings:	7
# Heavy Atoms:	10

MedChem Properties

QED Drug-Likeness Score:	0.379
Synthetic Accessibility Score:	7.26
Fsp3:	0.714
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:	-5.391
MDCK Permeability:	1.433697161701275e-05
Pgp-inhibitor:	0.996
Pgp-substrate:	0.9
Human Intestinal Absorption (HIA):	0.354
20% Bioavailability (F20%):	0.978
30% Bioavailability (F30%):	0.97

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.701
Plasma Protein Binding (PPB):	56.62071990966797%
Volume Distribution (VD):	0.769
Pgp-substrate:	45.707218170166016%

ADMET: Metabolism

CYP1A2-inhibitor:	0.004
CYP1A2-substrate:	0.966
CYP2C19-inhibitor:	0.02
CYP2C19-substrate:	0.685
CYP2C9-inhibitor:	0.013
CYP2C9-substrate:	0.014
CYP2D6-inhibitor:	0.001
CYP2D6-substrate:	0.067
CYP3A4-inhibitor:	0.567
CYP3A4-substrate:	0.87

ADMET: Excretion

Clearance (CL):	4.511
Half-life (T1/2):	0.566

ADMET: Toxicity

hERG Blockers:	0.098
Human Hepatotoxicity (H-HT):	0.103
Drug-inuced Liver Injury (DILI):	0.103
AMES Toxicity:	0.038
Rat Oral Acute Toxicity:	0.925
Maximum Recommended Daily Dose:	0.89
Skin Sensitization:	0.188
Carcinogencity:	0.815
Eye Corrosion:	0.003
Eye Irritation:	0.011
Respiratory Toxicity:	0.854

Download Data

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

Natural Product: NPC102316

Natural Product ID:	NPC102316
*Common Name:**	Physalin O
IUPAC Name:	n.a.
Synonyms:	Physalin O
Standard InCHIKey:	QFAOFAWTSOFSQA-HRLARMCRSA-N
Standard InCHI:	InChI=1S/C28H32O10/c1-12-21(32)36-17-11-23(12,2)19-20(31)27(35)18-14(24(3)13(10-15(18)29)6-5-7-16(24)30)8-9-26(34)22(33)37-25(17,4)28(19,26)38-27/h5,7,10,12,14-15,17-19,29,34-35H,6,8-9,11H2,1-4H3/t12-,14+,15-,17-,18+,19+,23-,24+,25+,26+,27-,28+/m1/s1
SMILES:	O[C@@H]1C=C2CC=CC(=O)[C@@]2([C@@H]2[C@@H]1[C@@]1(O)O[C@]34[C@@H](C1=O)[C@]1(C)C[C@H]([C@]4(C)OC(=O)[C@]3(CC2)O)OC(=O)[C@H]1C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL492224
PubChem CID:	44577489
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	3

Activity Type	# Activity
Cell Line	1
Individual Protein	1
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT113	Cell Line	RAW264.7	Mus musculus	IC50	=	17110.0	nM	PMID[450344]
NPT2601	Individual Protein	NF-kappaB inhibitor alpha	Homo sapiens	IC50	>	50000.0	nM	PMID[450345]
NPT2	Others	Unspecified		IC50	>	50000.0	nM	PMID[450345]

☑ 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 NPC102316 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	290
0.1-0.2	1578
0.2-0.3	4659
0.3-0.4	8141
0.4-0.5	12137
0.5-0.6	8429
0.6-0.7	5618
0.7-0.8	1693
0.8-0.85	133
0.85-0.9	11
0.9-0.95	5
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9754	High Similarity	NPC168879
0.9365	High Similarity	NPC243014
0.935	High Similarity	NPC264192
0.9206	High Similarity	NPC15215
0.9206	High Similarity	NPC242486
0.92	High Similarity	NPC254614
0.92	High Similarity	NPC100390
0.896	High Similarity	NPC188291
0.8898	High Similarity	NPC33378
0.8898	High Similarity	NPC254146
0.8898	High Similarity	NPC6274
0.8871	High Similarity	NPC470922
0.8871	High Similarity	NPC476729
0.879	High Similarity	NPC265557
0.879	High Similarity	NPC67251
0.879	High Similarity	NPC18945
0.879	High Similarity	NPC91693
0.879	High Similarity	NPC105926
0.872	High Similarity	NPC24651
0.871	High Similarity	NPC312833
0.8699	High Similarity	NPC112038
0.8689	High Similarity	NPC297179
0.8689	High Similarity	NPC17772
0.8689	High Similarity	NPC470776
0.8651	High Similarity	NPC181999
0.8629	High Similarity	NPC470779
0.8618	High Similarity	NPC470777
0.8618	High Similarity	NPC469488
0.8618	High Similarity	NPC268958
0.8561	High Similarity	NPC140045
0.8561	High Similarity	NPC295885
0.8548	High Similarity	NPC109607
0.8548	High Similarity	NPC107338
0.8537	High Similarity	NPC188667
0.8537	High Similarity	NPC251310
0.8537	High Similarity	NPC204552
0.8527	High Similarity	NPC476852
0.8525	High Similarity	NPC173686
0.8525	High Similarity	NPC474046
0.8525	High Similarity	NPC259306
0.8525	High Similarity	NPC134869
0.8525	High Similarity	NPC96312
0.8525	High Similarity	NPC328374
0.8525	High Similarity	NPC470628
0.8525	High Similarity	NPC40632
0.8525	High Similarity	NPC152199
0.8525	High Similarity	NPC474734
0.8525	High Similarity	NPC16081
0.8525	High Similarity	NPC251236
0.8525	High Similarity	NPC235539
0.8504	High Similarity	NPC225049
0.8485	Intermediate Similarity	NPC251998
0.8485	Intermediate Similarity	NPC190065
0.8485	Intermediate Similarity	NPC141215
0.8485	Intermediate Similarity	NPC471089
0.848	Intermediate Similarity	NPC102822
0.848	Intermediate Similarity	NPC477046
0.8468	Intermediate Similarity	NPC476529
0.8468	Intermediate Similarity	NPC475775
0.8455	Intermediate Similarity	NPC474654
0.8455	Intermediate Similarity	NPC287343
0.8455	Intermediate Similarity	NPC470775
0.8455	Intermediate Similarity	NPC97908
0.8455	Intermediate Similarity	NPC470854
0.8455	Intermediate Similarity	NPC477116
0.8455	Intermediate Similarity	NPC122033
0.8455	Intermediate Similarity	NPC176513
0.8455	Intermediate Similarity	NPC27999
0.845	Intermediate Similarity	NPC476851
0.8443	Intermediate Similarity	NPC469877
0.8443	Intermediate Similarity	NPC45218
0.8443	Intermediate Similarity	NPC143268
0.8443	Intermediate Similarity	NPC323821
0.8443	Intermediate Similarity	NPC473798
0.8443	Intermediate Similarity	NPC18547
0.8443	Intermediate Similarity	NPC268238
0.8443	Intermediate Similarity	NPC474906
0.8443	Intermediate Similarity	NPC470919
0.8438	Intermediate Similarity	NPC470882
0.8438	Intermediate Similarity	NPC476008
0.8421	Intermediate Similarity	NPC596
0.8409	Intermediate Similarity	NPC262813
0.8374	Intermediate Similarity	NPC207217
0.8374	Intermediate Similarity	NPC213084
0.8374	Intermediate Similarity	NPC190185
0.8372	Intermediate Similarity	NPC295220
0.8372	Intermediate Similarity	NPC476859
0.8372	Intermediate Similarity	NPC475636
0.8361	Intermediate Similarity	NPC49451
0.8361	Intermediate Similarity	NPC51978
0.8359	Intermediate Similarity	NPC477745
0.832	Intermediate Similarity	NPC472933
0.8308	Intermediate Similarity	NPC54614
0.8308	Intermediate Similarity	NPC309096
0.8306	Intermediate Similarity	NPC146432
0.8306	Intermediate Similarity	NPC473590
0.8306	Intermediate Similarity	NPC473968
0.8306	Intermediate Similarity	NPC470778
0.8295	Intermediate Similarity	NPC473265
0.8293	Intermediate Similarity	NPC117712
0.8293	Intermediate Similarity	NPC299849
0.8279	Intermediate Similarity	NPC11252
0.8279	Intermediate Similarity	NPC302146
0.8279	Intermediate Similarity	NPC289312
0.8264	Intermediate Similarity	NPC474567
0.8254	Intermediate Similarity	NPC109973
0.8244	Intermediate Similarity	NPC476863
0.8244	Intermediate Similarity	NPC476862
0.8244	Intermediate Similarity	NPC476855
0.8231	Intermediate Similarity	NPC473888
0.8226	Intermediate Similarity	NPC89929
0.8217	Intermediate Similarity	NPC87662
0.8211	Intermediate Similarity	NPC94509
0.8211	Intermediate Similarity	NPC208998
0.8211	Intermediate Similarity	NPC320118
0.8211	Intermediate Similarity	NPC198539
0.8211	Intermediate Similarity	NPC7921
0.8203	Intermediate Similarity	NPC227397
0.8197	Intermediate Similarity	NPC201992
0.8182	Intermediate Similarity	NPC478154
0.8168	Intermediate Similarity	NPC476854
0.8168	Intermediate Similarity	NPC470880
0.816	Intermediate Similarity	NPC218970
0.816	Intermediate Similarity	NPC472927
0.8154	Intermediate Similarity	NPC470780
0.8154	Intermediate Similarity	NPC473253
0.814	Intermediate Similarity	NPC473255
0.813	Intermediate Similarity	NPC205534
0.8125	Intermediate Similarity	NPC222688
0.812	Intermediate Similarity	NPC478151
0.8106	Intermediate Similarity	NPC25998
0.8106	Intermediate Similarity	NPC478155
0.8095	Intermediate Similarity	NPC234522
0.8095	Intermediate Similarity	NPC21326
0.8095	Intermediate Similarity	NPC106644
0.8092	Intermediate Similarity	NPC473620
0.8088	Intermediate Similarity	NPC477233
0.8088	Intermediate Similarity	NPC477232
0.808	Intermediate Similarity	NPC179626
0.808	Intermediate Similarity	NPC270478
0.8077	Intermediate Similarity	NPC285091
0.8077	Intermediate Similarity	NPC293112
0.8065	Intermediate Similarity	NPC194273
0.8062	Intermediate Similarity	NPC120724
0.8049	Intermediate Similarity	NPC157476
0.8049	Intermediate Similarity	NPC146945
0.8049	Intermediate Similarity	NPC171888
0.8047	Intermediate Similarity	NPC275675
0.8047	Intermediate Similarity	NPC202051
0.8045	Intermediate Similarity	NPC180902
0.8045	Intermediate Similarity	NPC478150
0.8045	Intermediate Similarity	NPC478152
0.8045	Intermediate Similarity	NPC475139
0.8045	Intermediate Similarity	NPC471855
0.8045	Intermediate Similarity	NPC478153
0.8033	Intermediate Similarity	NPC472534
0.8033	Intermediate Similarity	NPC143706
0.803	Intermediate Similarity	NPC477196
0.803	Intermediate Similarity	NPC231529
0.8016	Intermediate Similarity	NPC472934
0.8016	Intermediate Similarity	NPC469684
0.8	Intermediate Similarity	NPC247069
0.8	Intermediate Similarity	NPC172154
0.8	Intermediate Similarity	NPC8369
0.8	Intermediate Similarity	NPC7850
0.8	Intermediate Similarity	NPC6615
0.8	Intermediate Similarity	NPC81736
0.8	Intermediate Similarity	NPC243354
0.7984	Intermediate Similarity	NPC472002
0.7984	Intermediate Similarity	NPC269530
0.7984	Intermediate Similarity	NPC471965
0.7984	Intermediate Similarity	NPC474516
0.797	Intermediate Similarity	NPC301639
0.797	Intermediate Similarity	NPC477197
0.797	Intermediate Similarity	NPC264566
0.797	Intermediate Similarity	NPC329993
0.797	Intermediate Similarity	NPC478065
0.797	Intermediate Similarity	NPC475167
0.797	Intermediate Similarity	NPC172374
0.797	Intermediate Similarity	NPC134914
0.797	Intermediate Similarity	NPC476074
0.797	Intermediate Similarity	NPC262796
0.797	Intermediate Similarity	NPC475377
0.797	Intermediate Similarity	NPC45346
0.797	Intermediate Similarity	NPC173435
0.797	Intermediate Similarity	NPC478064
0.7969	Intermediate Similarity	NPC48692
0.7969	Intermediate Similarity	NPC478051
0.7967	Intermediate Similarity	NPC5103
0.7955	Intermediate Similarity	NPC477194
0.7955	Intermediate Similarity	NPC477191
0.7955	Intermediate Similarity	NPC477193
0.7955	Intermediate Similarity	NPC477192
0.7955	Intermediate Similarity	NPC245094
0.7951	Intermediate Similarity	NPC293850
0.7939	Intermediate Similarity	NPC473635
0.7937	Intermediate Similarity	NPC49492
0.7937	Intermediate Similarity	NPC266728
0.7926	Intermediate Similarity	NPC100017
0.7926	Intermediate Similarity	NPC475154

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 NPC102316 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	250
0.1-0.2	1782
0.2-0.3	3946
0.3-0.4	2057
0.4-0.5	640
0.5-0.6	264
0.6-0.7	152
0.7-0.8	51
0.8-0.85	8
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8	Intermediate Similarity	NPD7492	Approved
0.7969	Intermediate Similarity	NPD6054	Approved
0.7955	Intermediate Similarity	NPD7736	Approved
0.7939	Intermediate Similarity	NPD6616	Approved
0.7923	Intermediate Similarity	NPD8328	Phase 3
0.7879	Intermediate Similarity	NPD7078	Approved
0.7846	Intermediate Similarity	NPD6370	Approved
0.7829	Intermediate Similarity	NPD6319	Approved
0.7769	Intermediate Similarity	NPD6016	Approved
0.7769	Intermediate Similarity	NPD6015	Approved
0.771	Intermediate Similarity	NPD5988	Approved
0.7692	Intermediate Similarity	NPD6059	Approved
0.7661	Intermediate Similarity	NPD5345	Clinical (unspecified phase)
0.763	Intermediate Similarity	NPD7319	Approved
0.7612	Intermediate Similarity	NPD8293	Discontinued
0.7559	Intermediate Similarity	NPD8297	Approved
0.7559	Intermediate Similarity	NPD6882	Approved
0.748	Intermediate Similarity	NPD6649	Approved
0.748	Intermediate Similarity	NPD6650	Approved
0.7462	Intermediate Similarity	NPD7115	Discovery
0.7462	Intermediate Similarity	NPD8295	Clinical (unspecified phase)
0.7462	Intermediate Similarity	NPD6009	Approved
0.7407	Intermediate Similarity	NPD7507	Approved
0.7381	Intermediate Similarity	NPD6899	Approved
0.7381	Intermediate Similarity	NPD6881	Approved
0.7368	Intermediate Similarity	NPD8513	Phase 3
0.7368	Intermediate Similarity	NPD8515	Approved
0.7368	Intermediate Similarity	NPD8516	Approved
0.7368	Intermediate Similarity	NPD8517	Approved
0.7364	Intermediate Similarity	NPD4632	Approved
0.7323	Intermediate Similarity	NPD8132	Clinical (unspecified phase)
0.7323	Intermediate Similarity	NPD6373	Approved
0.7323	Intermediate Similarity	NPD6372	Approved
0.7302	Intermediate Similarity	NPD5697	Approved
0.7266	Intermediate Similarity	NPD7290	Approved
0.7266	Intermediate Similarity	NPD7102	Approved
0.7266	Intermediate Similarity	NPD6883	Approved
0.7244	Intermediate Similarity	NPD7320	Approved
0.7244	Intermediate Similarity	NPD6686	Approved
0.7222	Intermediate Similarity	NPD6402	Approved
0.7222	Intermediate Similarity	NPD5739	Approved
0.7222	Intermediate Similarity	NPD7128	Approved
0.7222	Intermediate Similarity	NPD6675	Approved
0.7209	Intermediate Similarity	NPD8130	Phase 1
0.7209	Intermediate Similarity	NPD6847	Approved
0.7209	Intermediate Similarity	NPD6869	Approved
0.7209	Intermediate Similarity	NPD6617	Approved
0.7188	Intermediate Similarity	NPD6014	Approved
0.7188	Intermediate Similarity	NPD6013	Approved
0.7188	Intermediate Similarity	NPD6012	Approved
0.7174	Intermediate Similarity	NPD6033	Approved
0.7132	Intermediate Similarity	NPD7604	Phase 2
0.7132	Intermediate Similarity	NPD4634	Approved
0.7111	Intermediate Similarity	NPD6921	Approved
0.7111	Intermediate Similarity	NPD5983	Phase 2
0.7109	Intermediate Similarity	NPD6011	Approved
0.709	Intermediate Similarity	NPD7516	Approved
0.7054	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.7031	Intermediate Similarity	NPD5701	Approved
0.7031	Intermediate Similarity	NPD6412	Phase 2
0.7029	Intermediate Similarity	NPD6336	Discontinued
0.7021	Intermediate Similarity	NPD7260	Phase 2
0.7016	Intermediate Similarity	NPD4225	Approved
0.7015	Intermediate Similarity	NPD7328	Approved
0.7015	Intermediate Similarity	NPD7327	Approved
0.7	Intermediate Similarity	NPD5955	Clinical (unspecified phase)
0.6984	Remote Similarity	NPD5211	Phase 2
0.6978	Remote Similarity	NPD8074	Phase 3
0.6947	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD5141	Approved
0.6861	Remote Similarity	NPD8380	Approved
0.6861	Remote Similarity	NPD8378	Approved
0.6861	Remote Similarity	NPD8379	Approved
0.6861	Remote Similarity	NPD7503	Approved
0.6861	Remote Similarity	NPD8335	Approved
0.6861	Remote Similarity	NPD8296	Approved
0.6853	Remote Similarity	NPD6845	Suspended
0.6838	Remote Similarity	NPD7100	Approved
0.6838	Remote Similarity	NPD7101	Approved
0.6825	Remote Similarity	NPD4696	Approved
0.6825	Remote Similarity	NPD5285	Approved
0.6825	Remote Similarity	NPD5286	Approved
0.6822	Remote Similarity	NPD6008	Approved
0.6818	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6788	Remote Similarity	NPD8294	Approved
0.6788	Remote Similarity	NPD8377	Approved
0.6781	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.6769	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6769	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6765	Remote Similarity	NPD6335	Approved
0.6748	Remote Similarity	NPD5779	Approved
0.6748	Remote Similarity	NPD5778	Approved
0.6746	Remote Similarity	NPD5696	Approved
0.6741	Remote Similarity	NPD6274	Approved
0.6739	Remote Similarity	NPD8033	Approved
0.6739	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.6719	Remote Similarity	NPD5226	Approved
0.6719	Remote Similarity	NPD4633	Approved
0.6719	Remote Similarity	NPD5224	Approved
0.6719	Remote Similarity	NPD5225	Approved
0.6713	Remote Similarity	NPD5956	Approved
0.6694	Remote Similarity	NPD5282	Discontinued
0.6693	Remote Similarity	NPD7640	Approved
0.6693	Remote Similarity	NPD7639	Approved
0.6691	Remote Similarity	NPD6317	Approved
0.6667	Remote Similarity	NPD6083	Phase 2
0.6667	Remote Similarity	NPD7902	Approved
0.6667	Remote Similarity	NPD6084	Phase 2
0.6667	Remote Similarity	NPD6411	Approved
0.6667	Remote Similarity	NPD5175	Approved
0.6667	Remote Similarity	NPD5174	Approved
0.6667	Remote Similarity	NPD4755	Approved
0.6642	Remote Similarity	NPD6313	Approved
0.6642	Remote Similarity	NPD6314	Approved
0.6641	Remote Similarity	NPD5344	Discontinued
0.6641	Remote Similarity	NPD5223	Approved
0.664	Remote Similarity	NPD5695	Phase 3
0.6618	Remote Similarity	NPD6868	Approved
0.6617	Remote Similarity	NPD6371	Approved
0.6614	Remote Similarity	NPD7638	Approved
0.6612	Remote Similarity	NPD3573	Approved
0.6593	Remote Similarity	NPD8133	Approved
0.6591	Remote Similarity	NPD4729	Approved
0.6591	Remote Similarity	NPD4730	Approved
0.6587	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6587	Remote Similarity	NPD5222	Approved
0.6587	Remote Similarity	NPD5221	Approved
0.6562	Remote Similarity	NPD4700	Approved
0.656	Remote Similarity	NPD7748	Approved
0.6535	Remote Similarity	NPD5173	Approved
0.6532	Remote Similarity	NPD7515	Phase 2
0.6532	Remote Similarity	NPD6079	Approved
0.6532	Remote Similarity	NPD7983	Approved
0.6508	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6508	Remote Similarity	NPD4629	Approved
0.6508	Remote Similarity	NPD5210	Approved
0.6507	Remote Similarity	NPD8338	Approved
0.6504	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6504	Remote Similarity	NPD6101	Approved
0.65	Remote Similarity	NPD6909	Approved
0.65	Remote Similarity	NPD6908	Approved
0.6493	Remote Similarity	NPD5251	Approved
0.6493	Remote Similarity	NPD5248	Approved
0.6493	Remote Similarity	NPD5249	Phase 3
0.6493	Remote Similarity	NPD5247	Approved
0.6493	Remote Similarity	NPD5250	Approved
0.6457	Remote Similarity	NPD4697	Phase 3
0.6439	Remote Similarity	NPD4768	Approved
0.6439	Remote Similarity	NPD4767	Approved
0.6429	Remote Similarity	NPD7900	Approved
0.6429	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6416	Remote Similarity	NPD8407	Phase 2
0.6408	Remote Similarity	NPD6067	Discontinued
0.64	Remote Similarity	NPD6333	Approved
0.64	Remote Similarity	NPD6334	Approved
0.6397	Remote Similarity	NPD6053	Discontinued
0.6391	Remote Similarity	NPD7799	Discontinued
0.6385	Remote Similarity	NPD1700	Approved
0.6376	Remote Similarity	NPD8387	Clinical (unspecified phase)
0.6371	Remote Similarity	NPD5328	Approved
0.6357	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6349	Remote Similarity	NPD6399	Phase 3
0.6343	Remote Similarity	NPD5128	Approved
0.6337	Remote Similarity	NPD8368	Discontinued
0.6324	Remote Similarity	NPD5215	Approved
0.6324	Remote Similarity	NPD5216	Approved
0.6324	Remote Similarity	NPD5217	Approved
0.632	Remote Similarity	NPD6698	Approved
0.632	Remote Similarity	NPD46	Approved
0.6311	Remote Similarity	NPD1694	Approved
0.6309	Remote Similarity	NPD8415	Approved
0.6308	Remote Similarity	NPD6648	Approved
0.629	Remote Similarity	NPD5737	Approved
0.629	Remote Similarity	NPD6672	Approved
0.6288	Remote Similarity	NPD4754	Approved
0.626	Remote Similarity	NPD3618	Phase 1
0.625	Remote Similarity	NPD5169	Approved
0.625	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.625	Remote Similarity	NPD8434	Phase 2
0.625	Remote Similarity	NPD5135	Approved
0.625	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.6233	Remote Similarity	NPD8336	Approved
0.6233	Remote Similarity	NPD8337	Approved
0.6212	Remote Similarity	NPD7632	Discontinued
0.6204	Remote Similarity	NPD5127	Approved
0.6202	Remote Similarity	NPD7839	Suspended
0.618	Remote Similarity	NPD8360	Approved
0.618	Remote Similarity	NPD8361	Approved
0.618	Remote Similarity	NPD8435	Approved
0.6148	Remote Similarity	NPD6110	Phase 1
0.6142	Remote Similarity	NPD6050	Approved
0.6142	Remote Similarity	NPD5284	Approved
0.6142	Remote Similarity	NPD5694	Approved
0.6142	Remote Similarity	NPD7637	Suspended
0.6142	Remote Similarity	NPD5281	Approved
0.6129	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6127	Remote Similarity	NPD4522	Approved
0.6119	Remote Similarity	NPD8170	Clinical (unspecified phase)
0.6111	Remote Similarity	NPD6673	Approved
0.6111	Remote Similarity	NPD4753	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