NPASS Compound

Structure

CID127235 OpenBabel06191715482D 27 29 0 0 1 0 0 0 0 0999 V2000 1.8074 2.5305 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8005 2.5827 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 2.5981 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2072 1.6691 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8660 -0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.4641 1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.5981 1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.7321 0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.7321 1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 4.3301 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0000 1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.8060 2.4781 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.0000 -2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.1854 1.4612 0.0000 O 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 -2.5981 1.5000 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 4.3301 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.0559 3.4464 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -0.0000 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 0.8660 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2 6 1 0 0 0 0 2 16 1 0 0 0 0 3 17 1 0 0 0 0 4 5 2 0 0 0 0 4 25 1 0 0 0 0 5 13 1 0 0 0 0 6 8 1 0 0 0 0 6 18 1 1 0 0 0 7 3 1 6 0 0 0 7 10 1 0 0 0 0 7 26 1 0 0 0 0 8 5 1 6 0 0 0 8 9 1 0 0 0 0 9 14 1 0 0 0 0 9 16 1 6 0 0 0 10 11 1 0 0 0 0 10 19 1 1 0 0 0 11 12 1 0 0 0 0 11 20 1 6 0 0 0 12 15 1 0 0 0 0 12 21 1 1 0 0 0 13 22 2 0 0 0 0 13 23 1 0 0 0 0 14 25 1 0 0 0 0 14 27 1 1 0 0 0 15 26 1 0 0 0 0 15 27 1 6 0 0 0 16 1 1 6 0 0 0 16 24 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	392.13
Volume:	351.042
LogP:	-1.076
LogD:	-0.459
LogS:	-0.717
# Rotatable Bonds:	4
TPSA:	186.37
# H-Bond Aceptor:	11
# H-Bond Donor:	7
# Rings:	3
# Heavy Atoms:	11

MedChem Properties

QED Drug-Likeness Score:	0.256
Synthetic Accessibility Score:	4.894
Fsp3:	0.812
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-6.503
MDCK Permeability:	0.0001662760623730719
Pgp-inhibitor:	0.0
Pgp-substrate:	0.732
Human Intestinal Absorption (HIA):	0.861
20% Bioavailability (F20%):	0.018
30% Bioavailability (F30%):	0.997

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.246
Plasma Protein Binding (PPB):	20.50454330444336%
Volume Distribution (VD):	0.284
Pgp-substrate:	57.195980072021484%

ADMET: Metabolism

CYP1A2-inhibitor:	0.012
CYP1A2-substrate:	0.045
CYP2C19-inhibitor:	0.013
CYP2C19-substrate:	0.053
CYP2C9-inhibitor:	0.002
CYP2C9-substrate:	0.054
CYP2D6-inhibitor:	0.007
CYP2D6-substrate:	0.088
CYP3A4-inhibitor:	0.014
CYP3A4-substrate:	0.015

ADMET: Excretion

Clearance (CL):	1.316
Half-life (T1/2):	0.874

ADMET: Toxicity

hERG Blockers:	0.057
Human Hepatotoxicity (H-HT):	0.266
Drug-inuced Liver Injury (DILI):	0.763
AMES Toxicity:	0.059
Rat Oral Acute Toxicity:	0.011
Maximum Recommended Daily Dose:	0.006
Skin Sensitization:	0.079
Carcinogencity:	0.922
Eye Corrosion:	0.003
Eye Irritation:	0.073
Respiratory Toxicity:	0.827

Download Data

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

Natural Product: NPC127235

Natural Product ID:	NPC127235
*Common Name:**	Shanzhiside
IUPAC Name:	(1S,4aS,5R,7S,7aS)-5,7-dihydroxy-7-methyl-1-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-4a,5,6,7a-tetrahydro-1H-cyclopenta[c]pyran-4-carboxylic acid
Synonyms:	Shanzhiside
Standard InCHIKey:	YSIFYNVXJOGADM-KDYWOABDSA-N
Standard InCHI:	InChI=1S/C16H24O11/c1-16(24)2-6(18)8-5(13(22)23)4-25-14(9(8)16)27-15-12(21)11(20)10(19)7(3-17)26-15/h4,6-12,14-15,17-21,24H,2-3H2,1H3,(H,22,23)/t6-,7-,8+,9-,10-,11+,12-,14+,15+,16+/m1/s1
SMILES:	OC[C@H]1O[C@@H](O[C@@H]2OC=C([C@@H]3[C@H]2[C@@](C)(O)C[C@H]3O)C(=O)O)[C@@H]([C@H]([C@@H]1O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL518392
PubChem CID:	11948668
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0002049] Terpene glycosides [CHEMONTID:0004081] Iridoid O-glycosides

*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
NPO9518	Gardenia jasminoides	Species	Rubiaceae	Eukaryota	Fruits	n.a.	n.a.	PMID[16309325]
NPO9518	Gardenia jasminoides	Species	Rubiaceae	Eukaryota	n.a.	Seoul, Korea	2000-Jun	PMID[16643034]
NPO9518	Gardenia jasminoides	Species	Rubiaceae	Eukaryota	fruit	n.a.	n.a.	PMID[18505286]
NPO9518	Gardenia jasminoides	Species	Rubiaceae	Eukaryota	fruit	n.a.	n.a.	PMID[19650637]
NPO9518	Gardenia jasminoides	Species	Rubiaceae	Eukaryota	fruits	n.a.	n.a.	PMID[23305920]
NPO5652	Barleria lupulina	Species	Acanthaceae	Eukaryota	aerial part	purchased in Vung Tau, Vietnam	2012-MAR	PMID[25611215]
NPO9518	Gardenia jasminoides	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[32141747]
NPO9518	Gardenia jasminoides	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO5652	Barleria lupulina	Species	Acanthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO5652	Barleria lupulina	Species	Acanthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO9518	Gardenia jasminoides	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO9518	Gardenia jasminoides	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO9518	Gardenia jasminoides	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO9518	Gardenia jasminoides	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5652	Barleria lupulina	Species	Acanthaceae	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
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT35	Others	n.a.		IC50	=	78.6	ug.mL-1	PMID[544759]

☑ 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 NPC127235 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	226
0.1-0.2	1527
0.2-0.3	5427
0.3-0.4	10526
0.4-0.5	11619
0.5-0.6	7621
0.6-0.7	5206
0.7-0.8	492
0.8-0.85	28
0.85-0.9	9
0.9-0.95	10
0.95-1	6

Similarity Score	Similarity Level	Natural Product ID
0.9697	High Similarity	NPC197813
0.9697	High Similarity	NPC80338
0.9697	High Similarity	NPC148270
0.9588	High Similarity	NPC3488
0.9588	High Similarity	NPC287539
0.9412	High Similarity	NPC193741
0.94	High Similarity	NPC170432
0.9394	High Similarity	NPC475928
0.9394	High Similarity	NPC37240
0.9293	High Similarity	NPC35185
0.9293	High Similarity	NPC4899
0.9293	High Similarity	NPC177013
0.9293	High Similarity	NPC474730
0.9231	High Similarity	NPC475851
0.9231	High Similarity	NPC475924
0.9216	High Similarity	NPC110701
0.9175	High Similarity	NPC161293
0.8911	High Similarity	NPC106668
0.8911	High Similarity	NPC304163
0.8824	High Similarity	NPC27687
0.8614	High Similarity	NPC37866
0.8586	High Similarity	NPC63897
0.8544	High Similarity	NPC80144
0.8447	Intermediate Similarity	NPC67296
0.8416	Intermediate Similarity	NPC474297
0.8384	Intermediate Similarity	NPC235051
0.8333	Intermediate Similarity	NPC261372
0.8333	Intermediate Similarity	NPC263674
0.8333	Intermediate Similarity	NPC58267
0.8317	Intermediate Similarity	NPC93869
0.8317	Intermediate Similarity	NPC6765
0.8269	Intermediate Similarity	NPC216911
0.8252	Intermediate Similarity	NPC49833
0.8252	Intermediate Similarity	NPC249171
0.8235	Intermediate Similarity	NPC284063
0.8218	Intermediate Similarity	NPC274588
0.82	Intermediate Similarity	NPC274274
0.82	Intermediate Similarity	NPC294643
0.82	Intermediate Similarity	NPC473150
0.8182	Intermediate Similarity	NPC50464
0.8182	Intermediate Similarity	NPC93190
0.8173	Intermediate Similarity	NPC476320
0.8173	Intermediate Similarity	NPC476211
0.8155	Intermediate Similarity	NPC236580
0.8155	Intermediate Similarity	NPC304445
0.8155	Intermediate Similarity	NPC86843
0.8113	Intermediate Similarity	NPC329834
0.8113	Intermediate Similarity	NPC473148
0.8095	Intermediate Similarity	NPC27474
0.8095	Intermediate Similarity	NPC476230
0.8095	Intermediate Similarity	NPC28304
0.8095	Intermediate Similarity	NPC298255
0.8061	Intermediate Similarity	NPC470657
0.8058	Intermediate Similarity	NPC241911
0.8058	Intermediate Similarity	NPC170527
0.8019	Intermediate Similarity	NPC195510
0.8019	Intermediate Similarity	NPC13171
0.8	Intermediate Similarity	NPC473146
0.8	Intermediate Similarity	NPC306344
0.8	Intermediate Similarity	NPC255677
0.8	Intermediate Similarity	NPC22149
0.7981	Intermediate Similarity	NPC471150
0.798	Intermediate Similarity	NPC31349
0.7963	Intermediate Similarity	NPC41681
0.7944	Intermediate Similarity	NPC329704
0.7931	Intermediate Similarity	NPC473228
0.7931	Intermediate Similarity	NPC470829
0.7925	Intermediate Similarity	NPC476228
0.7921	Intermediate Similarity	NPC120021
0.7921	Intermediate Similarity	NPC270908
0.7921	Intermediate Similarity	NPC470573
0.7921	Intermediate Similarity	NPC231710
0.7921	Intermediate Similarity	NPC216826
0.7921	Intermediate Similarity	NPC65665
0.787	Intermediate Similarity	NPC86095
0.785	Intermediate Similarity	NPC250545
0.785	Intermediate Similarity	NPC310804
0.785	Intermediate Similarity	NPC261117
0.783	Intermediate Similarity	NPC471381
0.783	Intermediate Similarity	NPC186861
0.781	Intermediate Similarity	NPC472290
0.7807	Intermediate Similarity	NPC277583
0.7788	Intermediate Similarity	NPC167893
0.7788	Intermediate Similarity	NPC472873
0.7778	Intermediate Similarity	NPC284929
0.7778	Intermediate Similarity	NPC118761
0.7778	Intermediate Similarity	NPC197541
0.7778	Intermediate Similarity	NPC234304
0.7778	Intermediate Similarity	NPC267869
0.7757	Intermediate Similarity	NPC471401
0.775	Intermediate Similarity	NPC152091
0.7745	Intermediate Similarity	NPC117596
0.7745	Intermediate Similarity	NPC246173
0.7705	Intermediate Similarity	NPC213634
0.77	Intermediate Similarity	NPC149018
0.77	Intermediate Similarity	NPC171484
0.7692	Intermediate Similarity	NPC71589
0.7685	Intermediate Similarity	NPC222062
0.7677	Intermediate Similarity	NPC3464
0.7677	Intermediate Similarity	NPC259296
0.7677	Intermediate Similarity	NPC98276
0.7677	Intermediate Similarity	NPC151176
0.7677	Intermediate Similarity	NPC475963
0.7672	Intermediate Similarity	NPC13710
0.767	Intermediate Similarity	NPC66504
0.767	Intermediate Similarity	NPC472126
0.767	Intermediate Similarity	NPC472124
0.767	Intermediate Similarity	NPC472125
0.7652	Intermediate Similarity	NPC88945
0.7647	Intermediate Similarity	NPC22918
0.7636	Intermediate Similarity	NPC54737
0.7632	Intermediate Similarity	NPC132668
0.7627	Intermediate Similarity	NPC42675
0.7619	Intermediate Similarity	NPC101051
0.7619	Intermediate Similarity	NPC476053
0.7611	Intermediate Similarity	NPC56025
0.76	Intermediate Similarity	NPC158350
0.7596	Intermediate Similarity	NPC61201
0.7593	Intermediate Similarity	NPC20673
0.7589	Intermediate Similarity	NPC118225
0.7589	Intermediate Similarity	NPC59489
0.7589	Intermediate Similarity	NPC471400
0.7589	Intermediate Similarity	NPC208307
0.7589	Intermediate Similarity	NPC139838
0.7586	Intermediate Similarity	NPC473304
0.7573	Intermediate Similarity	NPC216284
0.7573	Intermediate Similarity	NPC307699
0.757	Intermediate Similarity	NPC472015
0.7568	Intermediate Similarity	NPC254538
0.7568	Intermediate Similarity	NPC474285
0.7549	Intermediate Similarity	NPC148534
0.7523	Intermediate Similarity	NPC94919
0.7523	Intermediate Similarity	NPC471599
0.7522	Intermediate Similarity	NPC106760
0.7522	Intermediate Similarity	NPC114961
0.7522	Intermediate Similarity	NPC50223
0.7522	Intermediate Similarity	NPC27551
0.7521	Intermediate Similarity	NPC93368
0.75	Intermediate Similarity	NPC470373
0.75	Intermediate Similarity	NPC472197
0.75	Intermediate Similarity	NPC229752
0.75	Intermediate Similarity	NPC155529
0.75	Intermediate Similarity	NPC244878
0.75	Intermediate Similarity	NPC141196
0.75	Intermediate Similarity	NPC470379
0.75	Intermediate Similarity	NPC1980
0.75	Intermediate Similarity	NPC238005
0.7479	Intermediate Similarity	NPC202051
0.7478	Intermediate Similarity	NPC285086
0.7477	Intermediate Similarity	NPC474313
0.7477	Intermediate Similarity	NPC470683
0.7477	Intermediate Similarity	NPC470684
0.7477	Intermediate Similarity	NPC181151
0.7476	Intermediate Similarity	NPC215556
0.7476	Intermediate Similarity	NPC92974
0.7458	Intermediate Similarity	NPC219656
0.7456	Intermediate Similarity	NPC213320
0.7456	Intermediate Similarity	NPC122339
0.7456	Intermediate Similarity	NPC63244
0.7453	Intermediate Similarity	NPC36954
0.7453	Intermediate Similarity	NPC163228
0.7451	Intermediate Similarity	NPC258501
0.7451	Intermediate Similarity	NPC186148
0.7436	Intermediate Similarity	NPC78836
0.7436	Intermediate Similarity	NPC470171
0.7434	Intermediate Similarity	NPC8431
0.7431	Intermediate Similarity	NPC219038
0.7429	Intermediate Similarity	NPC475912
0.7429	Intermediate Similarity	NPC475788
0.7429	Intermediate Similarity	NPC258216
0.7422	Intermediate Similarity	NPC75616
0.7419	Intermediate Similarity	NPC173347
0.7417	Intermediate Similarity	NPC28532
0.7407	Intermediate Similarity	NPC151093
0.7407	Intermediate Similarity	NPC45125
0.7404	Intermediate Similarity	NPC474323
0.7404	Intermediate Similarity	NPC206614
0.7395	Intermediate Similarity	NPC281840
0.7391	Intermediate Similarity	NPC473303
0.7391	Intermediate Similarity	NPC471244
0.7391	Intermediate Similarity	NPC474927
0.7391	Intermediate Similarity	NPC471245
0.7391	Intermediate Similarity	NPC473397
0.7385	Intermediate Similarity	NPC48414
0.7385	Intermediate Similarity	NPC5153
0.7383	Intermediate Similarity	NPC306041
0.7383	Intermediate Similarity	NPC476009
0.7379	Intermediate Similarity	NPC79549
0.7379	Intermediate Similarity	NPC207114
0.7379	Intermediate Similarity	NPC177629
0.7379	Intermediate Similarity	NPC58219
0.7379	Intermediate Similarity	NPC217983
0.7377	Intermediate Similarity	NPC198714
0.7373	Intermediate Similarity	NPC475309
0.7368	Intermediate Similarity	NPC471476
0.7368	Intermediate Similarity	NPC130302
0.7368	Intermediate Similarity	NPC41551
0.7368	Intermediate Similarity	NPC98633
0.7368	Intermediate Similarity	NPC473324
0.7368	Intermediate Similarity	NPC471093

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 NPC127235 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	226
0.1-0.2	2119
0.2-0.3	3880
0.3-0.4	1946
0.4-0.5	548
0.5-0.6	281
0.6-0.7	148
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
0.7241	Intermediate Similarity	NPD6053	Discontinued
0.7236	Intermediate Similarity	NPD7507	Approved
0.7193	Intermediate Similarity	NPD6686	Approved
0.7179	Intermediate Similarity	NPD8133	Approved
0.7105	Intermediate Similarity	NPD6412	Phase 2
0.7063	Intermediate Similarity	NPD7319	Approved
0.7049	Intermediate Similarity	NPD8513	Phase 3
0.7049	Intermediate Similarity	NPD7503	Approved
0.7009	Intermediate Similarity	NPD8413	Clinical (unspecified phase)
0.6911	Remote Similarity	NPD8515	Approved
0.6911	Remote Similarity	NPD8517	Approved
0.6911	Remote Similarity	NPD8516	Approved
0.6857	Remote Similarity	NPD4249	Approved
0.681	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6792	Remote Similarity	NPD4250	Approved
0.6792	Remote Similarity	NPD4251	Approved
0.6786	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6783	Remote Similarity	NPD4057	Clinical (unspecified phase)
0.6783	Remote Similarity	NPD4056	Clinical (unspecified phase)
0.678	Remote Similarity	NPD6371	Approved
0.6774	Remote Similarity	NPD8033	Approved
0.6759	Remote Similarity	NPD46	Approved
0.6759	Remote Similarity	NPD6698	Approved
0.6721	Remote Similarity	NPD8137	Clinical (unspecified phase)
0.6721	Remote Similarity	NPD6009	Approved
0.672	Remote Similarity	NPD6370	Approved
0.6719	Remote Similarity	NPD7736	Approved
0.6697	Remote Similarity	NPD7983	Approved
0.6694	Remote Similarity	NPD6319	Approved
0.6667	Remote Similarity	NPD7328	Approved
0.6667	Remote Similarity	NPD7327	Approved
0.6667	Remote Similarity	NPD6882	Approved
0.6641	Remote Similarity	NPD8293	Discontinued
0.6635	Remote Similarity	NPD6435	Approved
0.6614	Remote Similarity	NPD7492	Approved
0.6613	Remote Similarity	NPD7516	Approved
0.6612	Remote Similarity	NPD4632	Approved
0.6587	Remote Similarity	NPD8080	Discontinued
0.6571	Remote Similarity	NPD7154	Phase 3
0.6562	Remote Similarity	NPD6616	Approved
0.656	Remote Similarity	NPD8294	Approved
0.656	Remote Similarity	NPD8377	Approved
0.656	Remote Similarity	NPD6054	Approved
0.6532	Remote Similarity	NPD7641	Discontinued
0.6529	Remote Similarity	NPD8297	Approved
0.6512	Remote Similarity	NPD7078	Approved
0.6508	Remote Similarity	NPD8379	Approved
0.6508	Remote Similarity	NPD8274	Clinical (unspecified phase)
0.6508	Remote Similarity	NPD6015	Approved
0.6508	Remote Similarity	NPD8380	Approved
0.6508	Remote Similarity	NPD8296	Approved
0.6508	Remote Similarity	NPD8378	Approved
0.6508	Remote Similarity	NPD6016	Approved
0.6508	Remote Similarity	NPD8335	Approved
0.6496	Remote Similarity	NPD8170	Clinical (unspecified phase)
0.6484	Remote Similarity	NPD8342	Approved
0.6484	Remote Similarity	NPD8341	Approved
0.6484	Remote Similarity	NPD8299	Approved
0.6484	Remote Similarity	NPD8340	Approved
0.6457	Remote Similarity	NPD5988	Approved
0.6452	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6446	Remote Similarity	NPD6649	Approved
0.6446	Remote Similarity	NPD6650	Approved
0.6442	Remote Similarity	NPD5368	Approved
0.6442	Remote Similarity	NPD4821	Approved
0.6442	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6442	Remote Similarity	NPD4822	Approved
0.6442	Remote Similarity	NPD4819	Approved
0.6442	Remote Similarity	NPD4820	Approved
0.6429	Remote Similarity	NPD6059	Approved
0.6417	Remote Similarity	NPD6373	Approved
0.6417	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6417	Remote Similarity	NPD6372	Approved
0.6415	Remote Similarity	NPD5362	Discontinued
0.6406	Remote Similarity	NPD8328	Phase 3
0.6389	Remote Similarity	NPD5786	Approved
0.6387	Remote Similarity	NPD5697	Approved
0.6385	Remote Similarity	NPD8074	Phase 3
0.6364	Remote Similarity	NPD1695	Approved
0.6339	Remote Similarity	NPD5779	Approved
0.6339	Remote Similarity	NPD5778	Approved
0.6333	Remote Similarity	NPD6881	Approved
0.6333	Remote Similarity	NPD6899	Approved
0.632	Remote Similarity	NPD7115	Discovery
0.6316	Remote Similarity	NPD7839	Suspended
0.6308	Remote Similarity	NPD8451	Approved
0.6303	Remote Similarity	NPD5739	Approved
0.6303	Remote Similarity	NPD6402	Approved
0.6303	Remote Similarity	NPD6675	Approved
0.6303	Remote Similarity	NPD7128	Approved
0.6303	Remote Similarity	NPD6008	Approved
0.6296	Remote Similarity	NPD5363	Approved
0.6296	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.6283	Remote Similarity	NPD5282	Discontinued
0.6281	Remote Similarity	NPD6014	Approved
0.6281	Remote Similarity	NPD6013	Approved
0.6281	Remote Similarity	NPD6012	Approved
0.6279	Remote Similarity	NPD7830	Approved
0.6279	Remote Similarity	NPD7642	Approved
0.6279	Remote Similarity	NPD7829	Approved
0.626	Remote Similarity	NPD8448	Approved
0.625	Remote Similarity	NPD5701	Approved
0.625	Remote Similarity	NPD4271	Approved
0.625	Remote Similarity	NPD4268	Approved
0.625	Remote Similarity	NPD5983	Phase 2
0.623	Remote Similarity	NPD7102	Approved
0.623	Remote Similarity	NPD7290	Approved
0.623	Remote Similarity	NPD6883	Approved
0.6226	Remote Similarity	NPD5369	Approved
0.6198	Remote Similarity	NPD7320	Approved
0.6198	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6198	Remote Similarity	NPD6011	Approved
0.6186	Remote Similarity	NPD8083	Approved
0.6186	Remote Similarity	NPD8139	Approved
0.6186	Remote Similarity	NPD8138	Approved
0.6186	Remote Similarity	NPD8085	Approved
0.6186	Remote Similarity	NPD5211	Phase 2
0.6186	Remote Similarity	NPD8086	Approved
0.6186	Remote Similarity	NPD8084	Approved
0.6186	Remote Similarity	NPD8082	Approved
0.6179	Remote Similarity	NPD8130	Phase 1
0.6179	Remote Similarity	NPD6869	Approved
0.6179	Remote Similarity	NPD6847	Approved
0.6179	Remote Similarity	NPD6617	Approved
0.6168	Remote Similarity	NPD4270	Approved
0.6168	Remote Similarity	NPD4269	Approved
0.6161	Remote Similarity	NPD5785	Approved
0.6161	Remote Similarity	NPD7838	Discovery
0.6154	Remote Similarity	NPD7604	Phase 2
0.6134	Remote Similarity	NPD8276	Approved
0.6134	Remote Similarity	NPD8275	Approved
0.6121	Remote Similarity	NPD6084	Phase 2
0.6121	Remote Similarity	NPD6083	Phase 2
0.6119	Remote Similarity	NPD8390	Approved
0.6119	Remote Similarity	NPD8392	Approved
0.6119	Remote Similarity	NPD8391	Approved
0.6111	Remote Similarity	NPD4788	Approved
0.6098	Remote Similarity	NPD4634	Approved
0.6095	Remote Similarity	NPD4802	Phase 2
0.6095	Remote Similarity	NPD4238	Approved
0.609	Remote Similarity	NPD8336	Approved
0.609	Remote Similarity	NPD8337	Approved
0.6087	Remote Similarity	NPD5695	Phase 3
0.6087	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6087	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.6083	Remote Similarity	NPD8081	Approved
0.6083	Remote Similarity	NPD5141	Approved
0.6071	Remote Similarity	NPD6101	Approved
0.6071	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6068	Remote Similarity	NPD4225	Approved
0.6068	Remote Similarity	NPD5696	Approved
0.6061	Remote Similarity	NPD6336	Discontinued
0.6053	Remote Similarity	NPD6399	Phase 3
0.6036	Remote Similarity	NPD7524	Approved
0.6033	Remote Similarity	NPD8393	Approved
0.6017	Remote Similarity	NPD7639	Approved
0.6017	Remote Similarity	NPD5285	Approved
0.6017	Remote Similarity	NPD7640	Approved
0.6017	Remote Similarity	NPD4696	Approved
0.6017	Remote Similarity	NPD5286	Approved
0.6	Remote Similarity	NPD8266	Approved
0.6	Remote Similarity	NPD8267	Approved
0.6	Remote Similarity	NPD8444	Approved
0.6	Remote Similarity	NPD8268	Approved
0.6	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6	Remote Similarity	NPD8269	Approved
0.5984	Remote Similarity	NPD6274	Approved
0.5983	Remote Similarity	NPD4755	Approved
0.5981	Remote Similarity	NPD4252	Approved
0.597	Remote Similarity	NPD6033	Approved
0.5966	Remote Similarity	NPD5344	Discontinued
0.5965	Remote Similarity	NPD6411	Approved
0.5965	Remote Similarity	NPD8035	Phase 2
0.5965	Remote Similarity	NPD8034	Phase 2
0.5965	Remote Similarity	NPD7637	Suspended
0.5963	Remote Similarity	NPD5331	Approved
0.5963	Remote Similarity	NPD5332	Approved
0.5963	Remote Similarity	NPD3670	Clinical (unspecified phase)
0.5963	Remote Similarity	NPD3669	Approved
0.5956	Remote Similarity	NPD7260	Phase 2
0.5932	Remote Similarity	NPD7638	Approved
0.5926	Remote Similarity	NPD1780	Approved
0.5926	Remote Similarity	NPD1779	Approved
0.5926	Remote Similarity	NPD4790	Discontinued
0.592	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.5917	Remote Similarity	NPD5226	Approved
0.5917	Remote Similarity	NPD5224	Approved
0.5917	Remote Similarity	NPD4633	Approved
0.5917	Remote Similarity	NPD5225	Approved
0.5912	Remote Similarity	NPD8338	Approved
0.5909	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.5909	Remote Similarity	NPD6067	Discontinued
0.5887	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.5882	Remote Similarity	NPD5956	Approved
0.5882	Remote Similarity	NPD4700	Approved
0.5868	Remote Similarity	NPD5175	Approved
0.5868	Remote Similarity	NPD5174	Approved
0.5854	Remote Similarity	NPD8307	Discontinued
0.5854	Remote Similarity	NPD8140	Approved
0.5846	Remote Similarity	NPD7100	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