NPASS Compound

Structure

CID198992 OpenBabel06191715592D 29 31 0 0 1 0 0 0 0 0999 V2000 5.1962 1.7321 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.7349 -3.7213 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.6962 0.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.6962 0.8660 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 6.0622 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -0.0000 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 5.4041 -2.9781 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 -0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 6.0622 -1.5000 0.0000 C 0 0 1 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 -0.8660 -1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0000 -2.0000 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 6.3986 -3.0827 0.0000 C 0 0 0 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 5.1962 0.0000 0.0000 C 0 0 1 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 -1.7321 -2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -3.0000 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 6.8986 -3.9487 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 6.8053 -2.1691 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 5 2 0 0 0 0 2 10 2 0 0 0 0 3 11 1 0 0 0 0 5 21 1 0 0 0 0 6 12 1 0 0 0 0 6 13 1 0 0 0 0 7 21 1 0 0 0 0 8 22 1 0 0 0 0 9 10 1 0 0 0 0 9 27 1 0 0 0 0 10 13 1 0 0 0 0 11 12 2 0 0 0 0 11 19 1 0 0 0 0 12 14 1 0 0 0 0 13 21 1 1 0 0 0 14 7 1 6 0 0 0 14 28 1 0 0 0 0 15 8 1 1 0 0 0 15 16 1 0 0 0 0 15 29 1 0 0 0 0 16 17 1 0 0 0 0 16 23 1 6 0 0 0 17 18 1 0 0 0 0 17 24 1 1 0 0 0 18 20 1 0 0 0 0 18 25 1 6 0 0 0 19 26 2 0 0 0 0 19 28 1 0 0 0 0 20 27 1 1 0 0 0 20 29 1 0 0 0 0 21 4 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	410.19
Volume:	405.879
LogP:	1.198
LogD:	1.626
LogS:	-2.147
# Rotatable Bonds:	6
TPSA:	132.75
# H-Bond Aceptor:	8
# H-Bond Donor:	5
# Rings:	3
# Heavy Atoms:	8

MedChem Properties

QED Drug-Likeness Score:	0.43
Synthetic Accessibility Score:	5.136
Fsp3:	0.619
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
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:	-5.801
MDCK Permeability:	7.399690730380826e-06
Pgp-inhibitor:	0.0
Pgp-substrate:	0.531
Human Intestinal Absorption (HIA):	0.198
20% Bioavailability (F20%):	0.442
30% Bioavailability (F30%):	0.4

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.081
Plasma Protein Binding (PPB):	80.8853530883789%
Volume Distribution (VD):	1.078
Pgp-substrate:	14.73438549041748%

ADMET: Metabolism

CYP1A2-inhibitor:	0.016
CYP1A2-substrate:	0.244
CYP2C19-inhibitor:	0.008
CYP2C19-substrate:	0.349
CYP2C9-inhibitor:	0.005
CYP2C9-substrate:	0.058
CYP2D6-inhibitor:	0.003
CYP2D6-substrate:	0.138
CYP3A4-inhibitor:	0.043
CYP3A4-substrate:	0.1

ADMET: Excretion

Clearance (CL):	1.602
Half-life (T1/2):	0.846

ADMET: Toxicity

hERG Blockers:	0.007
Human Hepatotoxicity (H-HT):	0.311
Drug-inuced Liver Injury (DILI):	0.707
AMES Toxicity:	0.853
Rat Oral Acute Toxicity:	0.531
Maximum Recommended Daily Dose:	0.044
Skin Sensitization:	0.162
Carcinogencity:	0.834
Eye Corrosion:	0.003
Eye Irritation:	0.012
Respiratory Toxicity:	0.616

Download Data

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

Natural Product: NPC198992

Natural Product ID:	NPC198992
*Common Name:**	Sarcaglaboside C
IUPAC Name:	(5R,6S,7aS)-6-ethenyl-3,6-dimethyl-5-[3-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyprop-1-en-2-yl]-4,5,7,7a-tetrahydro-1-benzofuran-2-one
Synonyms:	sarcaglaboside C
Standard InCHIKey:	JQVQMIABESRMFA-YYDGTUDOSA-N
Standard InCHI:	InChI=1S/C21H30O8/c1-5-21(4)7-14-12(11(3)19(26)28-14)6-13(21)10(2)9-27-20-18(25)17(24)16(23)15(8-22)29-20/h5,13-18,20,22-25H,1-2,6-9H2,3-4H3/t13-,14-,15+,16+,17-,18+,20+,21+/m0/s1
SMILES:	C=C[C@]1(C)C[C@H]2C(=C(C)C(=O)O2)C[C@H]1C(=C)CO[C@H]1[C@@H]([C@H]([C@@H]([C@@H](CO)O1)O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL520747
PubChem CID:	11596696
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0002049] Terpene 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
NPO29221	Sarcandra glabra	Species	Chloranthaceae	Eukaryota	Whole plant	n.a.	n.a.	PMID[16643038]
NPO29221	Sarcandra glabra	Species	Chloranthaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20038159]
NPO29221	Sarcandra glabra	Species	Chloranthaceae	Eukaryota	aerial part	n.a.	n.a.	PMID[25442304]
NPO29221	Sarcandra glabra	Species	Chloranthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO11301	Ulmus glabra	Species	Ulmaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO29221	Sarcandra glabra	Species	Chloranthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO11301	Ulmus glabra	Species	Ulmaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO463	Moschus berezovskii	Species	Moschidae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO463	Moschus berezovskii	Species	Moschidae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO29221	Sarcandra glabra	Species	Chloranthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO11301	Ulmus glabra	Species	Ulmaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10577	Loranthus glaber	Species	Loranthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9997	Pandanus dubius	Species	Pandanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9210	Desmodium uncinatum	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO463	Moschus berezovskii	Species	Moschidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29221	Sarcandra glabra	Species	Chloranthaceae	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
Others	2

Activity Type	# Activity
NON-MOLECULAR	1
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Inhibition	=	36.1	%	PMID[558681]
NPT27	Others	Unspecified		Activity	=	53.0	%	PMID[558681]

☑ 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 NPC198992 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	201
0.1-0.2	1205
0.2-0.3	4115
0.3-0.4	8045
0.4-0.5	12700
0.5-0.6	8116
0.6-0.7	5762
0.7-0.8	2279
0.8-0.85	226
0.85-0.9	44
0.9-0.95	2
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9588	High Similarity	NPC82251
0.9588	High Similarity	NPC239961
0.9479	High Similarity	NPC121423
0.9192	High Similarity	NPC85670
0.8922	High Similarity	NPC257853
0.8824	High Similarity	NPC392
0.8824	High Similarity	NPC177524
0.8824	High Similarity	NPC219900
0.87	High Similarity	NPC201191
0.8641	High Similarity	NPC135015
0.8641	High Similarity	NPC48548
0.8641	High Similarity	NPC128795
0.8641	High Similarity	NPC217921
0.8627	High Similarity	NPC218158
0.8614	High Similarity	NPC281378
0.8585	High Similarity	NPC264153
0.8558	High Similarity	NPC316974
0.8558	High Similarity	NPC206618
0.8558	High Similarity	NPC40728
0.8544	High Similarity	NPC125423
0.8544	High Similarity	NPC88013
0.8519	High Similarity	NPC474483
0.8515	High Similarity	NPC472815
0.8491	Intermediate Similarity	NPC328074
0.8491	Intermediate Similarity	NPC317460
0.8491	Intermediate Similarity	NPC470025
0.8491	Intermediate Similarity	NPC321272
0.8485	Intermediate Similarity	NPC91197
0.8485	Intermediate Similarity	NPC205143
0.8485	Intermediate Similarity	NPC239547
0.8485	Intermediate Similarity	NPC155319
0.8485	Intermediate Similarity	NPC96597
0.8485	Intermediate Similarity	NPC309503
0.8485	Intermediate Similarity	NPC125551
0.8476	Intermediate Similarity	NPC316708
0.8462	Intermediate Similarity	NPC311223
0.8462	Intermediate Similarity	NPC38948
0.8431	Intermediate Similarity	NPC127933
0.8431	Intermediate Similarity	NPC7644
0.8431	Intermediate Similarity	NPC7613
0.8431	Intermediate Similarity	NPC475889
0.8426	Intermediate Similarity	NPC193382
0.8426	Intermediate Similarity	NPC199428
0.8426	Intermediate Similarity	NPC99620
0.8426	Intermediate Similarity	NPC5311
0.8426	Intermediate Similarity	NPC310341
0.8416	Intermediate Similarity	NPC280991
0.8416	Intermediate Similarity	NPC477717
0.8416	Intermediate Similarity	NPC11974
0.8411	Intermediate Similarity	NPC473159
0.8411	Intermediate Similarity	NPC470027
0.84	Intermediate Similarity	NPC474440
0.8396	Intermediate Similarity	NPC470026
0.8396	Intermediate Similarity	NPC17791
0.8384	Intermediate Similarity	NPC165632
0.8365	Intermediate Similarity	NPC109376
0.835	Intermediate Similarity	NPC201880
0.835	Intermediate Similarity	NPC473207
0.835	Intermediate Similarity	NPC81567
0.835	Intermediate Similarity	NPC264867
0.835	Intermediate Similarity	NPC470321
0.8349	Intermediate Similarity	NPC203862
0.8349	Intermediate Similarity	NPC93883
0.8349	Intermediate Similarity	NPC99728
0.8349	Intermediate Similarity	NPC50305
0.8349	Intermediate Similarity	NPC244402
0.8349	Intermediate Similarity	NPC77319
0.8349	Intermediate Similarity	NPC157376
0.8349	Intermediate Similarity	NPC87250
0.8349	Intermediate Similarity	NPC473852
0.8349	Intermediate Similarity	NPC152615
0.8349	Intermediate Similarity	NPC471355
0.8349	Intermediate Similarity	NPC243196
0.8349	Intermediate Similarity	NPC471354
0.8349	Intermediate Similarity	NPC471353
0.8349	Intermediate Similarity	NPC474418
0.8349	Intermediate Similarity	NPC196429
0.8349	Intermediate Similarity	NPC309034
0.8349	Intermediate Similarity	NPC471351
0.8349	Intermediate Similarity	NPC34390
0.8349	Intermediate Similarity	NPC142066
0.8349	Intermediate Similarity	NPC27507
0.8349	Intermediate Similarity	NPC84987
0.8349	Intermediate Similarity	NPC158344
0.8333	Intermediate Similarity	NPC471633
0.8333	Intermediate Similarity	NPC150463
0.8333	Intermediate Similarity	NPC238397
0.8333	Intermediate Similarity	NPC69576
0.8333	Intermediate Similarity	NPC84949
0.8333	Intermediate Similarity	NPC471363
0.8333	Intermediate Similarity	NPC31354
0.8333	Intermediate Similarity	NPC472552
0.8317	Intermediate Similarity	NPC477716
0.8317	Intermediate Similarity	NPC477721
0.8317	Intermediate Similarity	NPC324841
0.8302	Intermediate Similarity	NPC177047
0.8302	Intermediate Similarity	NPC119550
0.8288	Intermediate Similarity	NPC470312
0.8288	Intermediate Similarity	NPC476150
0.8288	Intermediate Similarity	NPC476127
0.8286	Intermediate Similarity	NPC470024
0.8286	Intermediate Similarity	NPC224660
0.8286	Intermediate Similarity	NPC181994
0.8273	Intermediate Similarity	NPC473828
0.8273	Intermediate Similarity	NPC83287
0.8273	Intermediate Similarity	NPC473617
0.8269	Intermediate Similarity	NPC172867
0.8269	Intermediate Similarity	NPC51719
0.8265	Intermediate Similarity	NPC472195
0.8265	Intermediate Similarity	NPC472641
0.8265	Intermediate Similarity	NPC472640
0.8265	Intermediate Similarity	NPC472196
0.8265	Intermediate Similarity	NPC474835
0.8265	Intermediate Similarity	NPC238090
0.8265	Intermediate Similarity	NPC472812
0.8257	Intermediate Similarity	NPC471816
0.8257	Intermediate Similarity	NPC207637
0.8252	Intermediate Similarity	NPC120009
0.8252	Intermediate Similarity	NPC134270
0.8247	Intermediate Similarity	NPC202886
0.8235	Intermediate Similarity	NPC472554
0.8229	Intermediate Similarity	NPC472809
0.8229	Intermediate Similarity	NPC472810
0.8218	Intermediate Similarity	NPC477928
0.8214	Intermediate Similarity	NPC170084
0.8214	Intermediate Similarity	NPC476204
0.8198	Intermediate Similarity	NPC304260
0.8198	Intermediate Similarity	NPC55532
0.8198	Intermediate Similarity	NPC236973
0.8198	Intermediate Similarity	NPC470897
0.8198	Intermediate Similarity	NPC329905
0.8198	Intermediate Similarity	NPC32177
0.8198	Intermediate Similarity	NPC5883
0.8198	Intermediate Similarity	NPC44899
0.8198	Intermediate Similarity	NPC292467
0.8198	Intermediate Similarity	NPC470914
0.8198	Intermediate Similarity	NPC469756
0.8198	Intermediate Similarity	NPC30483
0.8198	Intermediate Similarity	NPC29639
0.819	Intermediate Similarity	NPC472390
0.819	Intermediate Similarity	NPC184512
0.819	Intermediate Similarity	NPC471205
0.819	Intermediate Similarity	NPC122816
0.8182	Intermediate Similarity	NPC159698
0.8182	Intermediate Similarity	NPC470255
0.8182	Intermediate Similarity	NPC25701
0.8182	Intermediate Similarity	NPC256368
0.8182	Intermediate Similarity	NPC211238
0.8182	Intermediate Similarity	NPC290693
0.8182	Intermediate Similarity	NPC2003
0.8173	Intermediate Similarity	NPC471937
0.8173	Intermediate Similarity	NPC470768
0.8173	Intermediate Similarity	NPC194941
0.8165	Intermediate Similarity	NPC106446
0.8163	Intermediate Similarity	NPC477749
0.8163	Intermediate Similarity	NPC472811
0.8155	Intermediate Similarity	NPC214277
0.8155	Intermediate Similarity	NPC470571
0.8148	Intermediate Similarity	NPC473125
0.8144	Intermediate Similarity	NPC477748
0.8144	Intermediate Similarity	NPC470734
0.8137	Intermediate Similarity	NPC130792
0.8137	Intermediate Similarity	NPC16601
0.8137	Intermediate Similarity	NPC38855
0.8131	Intermediate Similarity	NPC83005
0.8131	Intermediate Similarity	NPC476766
0.8125	Intermediate Similarity	NPC475629
0.8125	Intermediate Similarity	NPC72260
0.8125	Intermediate Similarity	NPC474466
0.8125	Intermediate Similarity	NPC475556
0.8125	Intermediate Similarity	NPC475136
0.8125	Intermediate Similarity	NPC48692
0.8125	Intermediate Similarity	NPC135369
0.8119	Intermediate Similarity	NPC477718
0.8119	Intermediate Similarity	NPC240372
0.8119	Intermediate Similarity	NPC477719
0.8108	Intermediate Similarity	NPC218093
0.8108	Intermediate Similarity	NPC470515
0.8095	Intermediate Similarity	NPC252296
0.8095	Intermediate Similarity	NPC470763
0.8095	Intermediate Similarity	NPC470767
0.8081	Intermediate Similarity	NPC474792
0.8081	Intermediate Similarity	NPC67398
0.8081	Intermediate Similarity	NPC91654
0.8081	Intermediate Similarity	NPC110022
0.8081	Intermediate Similarity	NPC53555
0.8081	Intermediate Similarity	NPC156553
0.8077	Intermediate Similarity	NPC473070
0.8077	Intermediate Similarity	NPC23584
0.8077	Intermediate Similarity	NPC471938
0.8073	Intermediate Similarity	NPC40133
0.8073	Intermediate Similarity	NPC290608
0.8073	Intermediate Similarity	NPC293658
0.8073	Intermediate Similarity	NPC44298
0.8073	Intermediate Similarity	NPC473128
0.8073	Intermediate Similarity	NPC474410
0.8073	Intermediate Similarity	NPC49413
0.8073	Intermediate Similarity	NPC75167
0.8073	Intermediate Similarity	NPC311592
0.807	Intermediate Similarity	NPC27363

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 NPC198992 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	171
0.1-0.2	1412
0.2-0.3	3802
0.3-0.4	2392
0.4-0.5	885
0.5-0.6	297
0.6-0.7	161
0.7-0.8	29
0.8-0.85	0
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8824	High Similarity	NPD6686	Approved
0.8273	Intermediate Similarity	NPD7327	Approved
0.8273	Intermediate Similarity	NPD7328	Approved
0.8198	Intermediate Similarity	NPD7516	Approved
0.8125	Intermediate Similarity	NPD8377	Approved
0.8125	Intermediate Similarity	NPD8294	Approved
0.8053	Intermediate Similarity	NPD8335	Approved
0.8053	Intermediate Similarity	NPD8378	Approved
0.8053	Intermediate Similarity	NPD8380	Approved
0.8053	Intermediate Similarity	NPD8033	Approved
0.8053	Intermediate Similarity	NPD8296	Approved
0.8053	Intermediate Similarity	NPD8379	Approved
0.7931	Intermediate Similarity	NPD7507	Approved
0.7895	Intermediate Similarity	NPD7503	Approved
0.7731	Intermediate Similarity	NPD7319	Approved
0.7692	Intermediate Similarity	NPD4225	Approved
0.7547	Intermediate Similarity	NPD5344	Discontinued
0.7525	Intermediate Similarity	NPD7838	Discovery
0.7525	Intermediate Similarity	NPD46	Approved
0.7525	Intermediate Similarity	NPD6698	Approved
0.7524	Intermediate Similarity	NPD7638	Approved
0.7524	Intermediate Similarity	NPD8029	Clinical (unspecified phase)
0.7523	Intermediate Similarity	NPD6412	Phase 2
0.7453	Intermediate Similarity	NPD7640	Approved
0.7453	Intermediate Similarity	NPD7639	Approved
0.7449	Intermediate Similarity	NPD6400	Clinical (unspecified phase)
0.7434	Intermediate Similarity	NPD8133	Approved
0.7387	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.7232	Intermediate Similarity	NPD8132	Clinical (unspecified phase)
0.7168	Intermediate Similarity	NPD5955	Clinical (unspecified phase)
0.7167	Intermediate Similarity	NPD8328	Phase 3
0.7143	Intermediate Similarity	NPD8516	Approved
0.7143	Intermediate Similarity	NPD8515	Approved
0.7143	Intermediate Similarity	NPD8513	Phase 3
0.7143	Intermediate Similarity	NPD8517	Approved
0.713	Intermediate Similarity	NPD6648	Approved
0.7105	Intermediate Similarity	NPD8413	Clinical (unspecified phase)
0.6903	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.69	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6847	Remote Similarity	NPD7632	Discontinued
0.6807	Remote Similarity	NPD6009	Approved
0.6807	Remote Similarity	NPD7115	Discovery
0.6807	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6803	Remote Similarity	NPD6370	Approved
0.68	Remote Similarity	NPD7736	Approved
0.6792	Remote Similarity	NPD7637	Suspended
0.6777	Remote Similarity	NPD6319	Approved
0.6752	Remote Similarity	NPD6882	Approved
0.6724	Remote Similarity	NPD6371	Approved
0.672	Remote Similarity	NPD8293	Discontinued
0.6696	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6695	Remote Similarity	NPD4632	Approved
0.6694	Remote Similarity	NPD7492	Approved
0.664	Remote Similarity	NPD6616	Approved
0.6639	Remote Similarity	NPD6054	Approved
0.6636	Remote Similarity	NPD7983	Approved
0.6613	Remote Similarity	NPD7830	Approved
0.6613	Remote Similarity	NPD7829	Approved
0.661	Remote Similarity	NPD8297	Approved
0.6609	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6587	Remote Similarity	NPD7078	Approved
0.6587	Remote Similarity	NPD8074	Phase 3
0.6585	Remote Similarity	NPD6016	Approved
0.6585	Remote Similarity	NPD6015	Approved
0.6574	Remote Similarity	NPD5778	Approved
0.6574	Remote Similarity	NPD5779	Approved
0.6571	Remote Similarity	NPD7524	Approved
0.6569	Remote Similarity	NPD7625	Phase 1
0.6538	Remote Similarity	NPD1694	Approved
0.6532	Remote Similarity	NPD5988	Approved
0.6504	Remote Similarity	NPD6059	Approved
0.6481	Remote Similarity	NPD6411	Approved
0.648	Remote Similarity	NPD6067	Discontinued
0.6466	Remote Similarity	NPD5697	Approved
0.6455	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6442	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.641	Remote Similarity	NPD6881	Approved
0.641	Remote Similarity	NPD6899	Approved
0.6391	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.6387	Remote Similarity	NPD6650	Approved
0.6387	Remote Similarity	NPD6649	Approved
0.6379	Remote Similarity	NPD7128	Approved
0.6379	Remote Similarity	NPD5739	Approved
0.6379	Remote Similarity	NPD6402	Approved
0.6379	Remote Similarity	NPD6675	Approved
0.6378	Remote Similarity	NPD8451	Approved
0.6364	Remote Similarity	NPD5282	Discontinued
0.6364	Remote Similarity	NPD7748	Approved
0.6356	Remote Similarity	NPD6372	Approved
0.6356	Remote Similarity	NPD6013	Approved
0.6356	Remote Similarity	NPD6014	Approved
0.6356	Remote Similarity	NPD6012	Approved
0.6356	Remote Similarity	NPD6373	Approved
0.6349	Remote Similarity	NPD7642	Approved
0.6346	Remote Similarity	NPD6695	Phase 3
0.6341	Remote Similarity	NPD7641	Discontinued
0.6339	Remote Similarity	NPD7902	Approved
0.6333	Remote Similarity	NPD6053	Discontinued
0.633	Remote Similarity	NPD7515	Phase 2
0.6328	Remote Similarity	NPD8448	Approved
0.6325	Remote Similarity	NPD5701	Approved
0.6321	Remote Similarity	NPD4249	Approved
0.632	Remote Similarity	NPD8444	Approved
0.632	Remote Similarity	NPD5983	Phase 2
0.6303	Remote Similarity	NPD6883	Approved
0.6303	Remote Similarity	NPD7102	Approved
0.6303	Remote Similarity	NPD7290	Approved
0.6296	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6296	Remote Similarity	NPD6101	Approved
0.6273	Remote Similarity	NPD6399	Phase 3
0.6271	Remote Similarity	NPD7320	Approved
0.6271	Remote Similarity	NPD6011	Approved
0.6262	Remote Similarity	NPD4251	Approved
0.6262	Remote Similarity	NPD4250	Approved
0.625	Remote Similarity	NPD8130	Phase 1
0.625	Remote Similarity	NPD7839	Suspended
0.625	Remote Similarity	NPD6847	Approved
0.625	Remote Similarity	NPD6617	Approved
0.625	Remote Similarity	NPD6869	Approved
0.6239	Remote Similarity	NPD5785	Approved
0.6239	Remote Similarity	NPD3168	Discontinued
0.6226	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.622	Remote Similarity	NPD7604	Phase 2
0.6214	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6195	Remote Similarity	NPD6083	Phase 2
0.6195	Remote Similarity	NPD6084	Phase 2
0.619	Remote Similarity	NPD3670	Clinical (unspecified phase)
0.619	Remote Similarity	NPD3669	Approved
0.619	Remote Similarity	NPD6921	Approved
0.6183	Remote Similarity	NPD8392	Approved
0.6183	Remote Similarity	NPD8390	Approved
0.6183	Remote Similarity	NPD8391	Approved
0.6172	Remote Similarity	NPD8340	Approved
0.6172	Remote Similarity	NPD8341	Approved
0.6172	Remote Similarity	NPD8299	Approved
0.6172	Remote Similarity	NPD8342	Approved
0.6168	Remote Similarity	NPD3618	Phase 1
0.6167	Remote Similarity	NPD4634	Approved
0.6161	Remote Similarity	NPD5695	Phase 3
0.6147	Remote Similarity	NPD6051	Approved
0.6142	Remote Similarity	NPD8080	Discontinued
0.6136	Remote Similarity	NPD7260	Phase 2
0.6129	Remote Similarity	NPD8137	Clinical (unspecified phase)
0.6129	Remote Similarity	NPD7505	Discontinued
0.6126	Remote Similarity	NPD8171	Discontinued
0.6124	Remote Similarity	NPD6336	Discontinued
0.6122	Remote Similarity	NPD7532	Clinical (unspecified phase)
0.6121	Remote Similarity	NPD5211	Phase 2
0.6117	Remote Similarity	NPD6929	Approved
0.6111	Remote Similarity	NPD7750	Discontinued
0.6106	Remote Similarity	NPD4792	Clinical (unspecified phase)
0.6102	Remote Similarity	NPD4211	Phase 1
0.6102	Remote Similarity	NPD6008	Approved
0.6095	Remote Similarity	NPD5209	Approved
0.6087	Remote Similarity	NPD4696	Approved
0.6087	Remote Similarity	NPD5286	Approved
0.6087	Remote Similarity	NPD5285	Approved
0.6071	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6071	Remote Similarity	NPD7900	Approved
0.6058	Remote Similarity	NPD6931	Approved
0.6058	Remote Similarity	NPD4820	Approved
0.6058	Remote Similarity	NPD4819	Approved
0.6058	Remote Similarity	NPD4821	Approved
0.6058	Remote Similarity	NPD6930	Phase 2
0.6058	Remote Similarity	NPD7514	Phase 3
0.6058	Remote Similarity	NPD4822	Approved
0.6058	Remote Similarity	NPD7332	Phase 2
0.6058	Remote Similarity	NPD7525	Registered
0.6053	Remote Similarity	NPD4755	Approved
0.6038	Remote Similarity	NPD7154	Phase 3
0.6036	Remote Similarity	NPD6079	Approved
0.6031	Remote Similarity	NPD6033	Approved
0.6019	Remote Similarity	NPD4271	Approved
0.6019	Remote Similarity	NPD6409	Approved
0.6019	Remote Similarity	NPD7145	Approved
0.6019	Remote Similarity	NPD7521	Approved
0.6019	Remote Similarity	NPD6684	Approved
0.6019	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6019	Remote Similarity	NPD7334	Approved
0.6019	Remote Similarity	NPD7146	Approved
0.6019	Remote Similarity	NPD4268	Approved
0.6019	Remote Similarity	NPD5330	Approved
0.6017	Remote Similarity	NPD8170	Clinical (unspecified phase)
0.6017	Remote Similarity	NPD5141	Approved
0.6016	Remote Similarity	NPD5125	Phase 3
0.6016	Remote Similarity	NPD5126	Approved
0.6	Remote Similarity	NPD5696	Approved
0.6	Remote Similarity	NPD5328	Approved
0.6	Remote Similarity	NPD8415	Approved
0.6	Remote Similarity	NPD7266	Discontinued
0.6	Remote Similarity	NPD6902	Approved
0.5984	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.5983	Remote Similarity	NPD4633	Approved
0.5983	Remote Similarity	NPD5224	Approved
0.5983	Remote Similarity	NPD5225	Approved
0.5983	Remote Similarity	NPD5226	Approved
0.5982	Remote Similarity	NPD4202	Approved
0.5981	Remote Similarity	NPD3665	Phase 1
0.5981	Remote Similarity	NPD3666	Approved
0.5981	Remote Similarity	NPD3133	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