NPASS Compound

Structure

CID82251 OpenBabel06191715422D 29 32 0 0 1 0 0 0 0 0999 V2000 -4.3301 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0514 -2.9612 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 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 -4.3301 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0733 -3.1691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -2.5000 0.0000 C 0 0 0 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 -3.4641 -3.0000 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 -1.7321 -1.0000 0.0000 C 0 0 1 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 -4.6665 -4.0827 0.0000 C 0 0 0 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 -2.5981 -1.5000 0.0000 C 0 0 1 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 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 -5.1665 -4.9487 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.6720 -3.9781 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 1 9 2 0 0 0 0 2 10 1 0 0 0 0 4 5 2 0 0 0 0 4 9 1 0 0 0 0 5 15 1 0 0 0 0 6 11 1 0 0 0 0 6 12 1 0 0 0 0 7 21 1 0 0 0 0 8 22 1 0 0 0 0 9 12 1 0 0 0 0 10 11 2 0 0 0 0 10 19 1 0 0 0 0 11 13 1 0 0 0 0 12 21 1 1 0 0 0 13 7 1 6 0 0 0 13 27 1 0 0 0 0 14 8 1 6 0 0 0 14 16 1 0 0 0 0 14 28 1 0 0 0 0 15 21 1 6 0 0 0 15 29 1 0 0 0 0 16 17 1 0 0 0 0 16 23 1 1 0 0 0 17 18 1 0 0 0 0 17 24 1 6 0 0 0 18 20 1 0 0 0 0 18 25 1 1 0 0 0 19 26 2 0 0 0 0 19 27 1 0 0 0 0 20 28 1 0 0 0 0 20 29 1 6 0 0 0 21 3 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	408.18
Volume:	397.322
LogP:	1.409
LogD:	0.854
LogS:	-2.273
# Rotatable Bonds:	3
TPSA:	132.75
# H-Bond Aceptor:	8
# H-Bond Donor:	5
# Rings:	4
# Heavy Atoms:	8

MedChem Properties

QED Drug-Likeness Score:	0.483
Synthetic Accessibility Score:	5.2
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:	-5.72
MDCK Permeability:	1.0476287570782006e-05
Pgp-inhibitor:	0.002
Pgp-substrate:	0.949
Human Intestinal Absorption (HIA):	0.884
20% Bioavailability (F20%):	0.008
30% Bioavailability (F30%):	0.851

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.156
Plasma Protein Binding (PPB):	81.00715637207031%
Volume Distribution (VD):	1.127
Pgp-substrate:	16.52254295349121%

ADMET: Metabolism

CYP1A2-inhibitor:	0.023
CYP1A2-substrate:	0.055
CYP2C19-inhibitor:	0.009
CYP2C19-substrate:	0.267
CYP2C9-inhibitor:	0.005
CYP2C9-substrate:	0.062
CYP2D6-inhibitor:	0.002
CYP2D6-substrate:	0.157
CYP3A4-inhibitor:	0.02
CYP3A4-substrate:	0.139

ADMET: Excretion

Clearance (CL):	4.584
Half-life (T1/2):	0.841

ADMET: Toxicity

hERG Blockers:	0.019
Human Hepatotoxicity (H-HT):	0.173
Drug-inuced Liver Injury (DILI):	0.868
AMES Toxicity:	0.618
Rat Oral Acute Toxicity:	0.793
Maximum Recommended Daily Dose:	0.955
Skin Sensitization:	0.762
Carcinogencity:	0.845
Eye Corrosion:	0.003
Eye Irritation:	0.01
Respiratory Toxicity:	0.975

Download Data

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

Natural Product: NPC82251

Natural Product ID:	NPC82251
*Common Name:**	Sarcaglaboside B
IUPAC Name:	(4aS,8S,8aR,9aS)-3,8a-dimethyl-5-methylidene-8-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-4a,8,9,9a-tetrahydro-4H-benzo[f][1]benzofuran-2-one
Synonyms:	sarcaglaboside B
Standard InCHIKey:	IXPRKLBCFLYFKW-BVFXZANDSA-N
Standard InCHI:	InChI=1S/C21H28O8/c1-9-4-5-15(29-20-18(25)17(24)16(23)14(8-22)28-20)21(3)7-13-11(6-12(9)21)10(2)19(26)27-13/h4-5,12-18,20,22-25H,1,6-8H2,2-3H3/t12-,13-,14+,15-,16+,17-,18+,20-,21+/m0/s1
SMILES:	OC[C@H]1O[C@@H](O[C@H]2C=CC(=C)[C@H]3[C@@]2(C)C[C@@H]2OC(=O)C(=C2C3)C)[C@@H]([C@H]([C@@H]1O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL519466
PubChem CID:	11545986
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001283] Terpene lactones [CHEMONTID:0001543] Sesquiterpene lactones [CHEMONTID:0001772] Eudesmanolides, secoeudesmanolides, 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
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]
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]
NPO29221	Sarcandra glabra	Species	Chloranthaceae	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]
NPO29221	Sarcandra glabra	Species	Chloranthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
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]

☑ 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	=	65.9	%	PMID[504751]
NPT27	Others	Unspecified		Activity	=	74.9	%	PMID[504751]

☑ 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 NPC82251 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	203
0.1-0.2	1136
0.2-0.3	3861
0.3-0.4	7002
0.4-0.5	13363
0.5-0.6	8864
0.6-0.7	5736
0.7-0.8	2304
0.8-0.85	193
0.85-0.9	29
0.9-0.95	4
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9588	High Similarity	NPC198992
0.9293	High Similarity	NPC121423
0.9208	High Similarity	NPC239961
0.8835	High Similarity	NPC85670
0.8762	High Similarity	NPC316974
0.8725	High Similarity	NPC201191
0.8692	High Similarity	NPC321272
0.8692	High Similarity	NPC470025
0.8692	High Similarity	NPC317460
0.8692	High Similarity	NPC328074
0.8679	High Similarity	NPC316708
0.8667	High Similarity	NPC135015
0.8667	High Similarity	NPC48548
0.8667	High Similarity	NPC128795
0.8667	High Similarity	NPC219900
0.8667	High Similarity	NPC392
0.8667	High Similarity	NPC311223
0.8667	High Similarity	NPC217921
0.8667	High Similarity	NPC177524
0.8654	High Similarity	NPC218158
0.8611	High Similarity	NPC470027
0.8598	High Similarity	NPC470026
0.8598	High Similarity	NPC17791
0.8585	High Similarity	NPC40728
0.8585	High Similarity	NPC257853
0.8571	High Similarity	NPC109376
0.8571	High Similarity	NPC125423
0.8571	High Similarity	NPC88013
0.8558	High Similarity	NPC470321
0.8558	High Similarity	NPC201880
0.8558	High Similarity	NPC473207
0.8558	High Similarity	NPC81567
0.8558	High Similarity	NPC264867
0.8515	High Similarity	NPC96597
0.8515	High Similarity	NPC309503
0.8515	High Similarity	NPC91197
0.8515	High Similarity	NPC239547
0.8515	High Similarity	NPC155319
0.8515	High Similarity	NPC125551
0.8505	High Similarity	NPC119550
0.8505	High Similarity	NPC177047
0.8491	Intermediate Similarity	NPC470024
0.8491	Intermediate Similarity	NPC224660
0.8476	Intermediate Similarity	NPC172867
0.8468	Intermediate Similarity	NPC473828
0.8468	Intermediate Similarity	NPC473617
0.8462	Intermediate Similarity	NPC475889
0.8462	Intermediate Similarity	NPC7613
0.8462	Intermediate Similarity	NPC134270
0.8462	Intermediate Similarity	NPC127933
0.8462	Intermediate Similarity	NPC7644
0.8462	Intermediate Similarity	NPC281378
0.8447	Intermediate Similarity	NPC280991
0.844	Intermediate Similarity	NPC473159
0.844	Intermediate Similarity	NPC264153
0.8431	Intermediate Similarity	NPC474440
0.8396	Intermediate Similarity	NPC184512
0.8378	Intermediate Similarity	NPC474483
0.8378	Intermediate Similarity	NPC203862
0.8365	Intermediate Similarity	NPC238397
0.8365	Intermediate Similarity	NPC471363
0.8365	Intermediate Similarity	NPC470571
0.8364	Intermediate Similarity	NPC106446
0.8333	Intermediate Similarity	NPC205143
0.8302	Intermediate Similarity	NPC252296
0.8288	Intermediate Similarity	NPC5311
0.8288	Intermediate Similarity	NPC310341
0.8288	Intermediate Similarity	NPC199428
0.8288	Intermediate Similarity	NPC193382
0.8288	Intermediate Similarity	NPC207637
0.8288	Intermediate Similarity	NPC99620
0.8286	Intermediate Similarity	NPC23584
0.8269	Intermediate Similarity	NPC477717
0.8269	Intermediate Similarity	NPC11974
0.8252	Intermediate Similarity	NPC477928
0.8246	Intermediate Similarity	NPC233500
0.8246	Intermediate Similarity	NPC476204
0.8246	Intermediate Similarity	NPC170084
0.8241	Intermediate Similarity	NPC206618
0.8235	Intermediate Similarity	NPC165632
0.823	Intermediate Similarity	NPC219656
0.823	Intermediate Similarity	NPC153085
0.823	Intermediate Similarity	NPC268326
0.823	Intermediate Similarity	NPC470914
0.8224	Intermediate Similarity	NPC472390
0.8218	Intermediate Similarity	NPC294293
0.8218	Intermediate Similarity	NPC470255
0.8214	Intermediate Similarity	NPC152615
0.8214	Intermediate Similarity	NPC309034
0.8214	Intermediate Similarity	NPC87250
0.8214	Intermediate Similarity	NPC34390
0.8214	Intermediate Similarity	NPC142066
0.8214	Intermediate Similarity	NPC473852
0.8214	Intermediate Similarity	NPC158344
0.8214	Intermediate Similarity	NPC474418
0.8214	Intermediate Similarity	NPC196429
0.8214	Intermediate Similarity	NPC84987
0.8214	Intermediate Similarity	NPC157376
0.8214	Intermediate Similarity	NPC471355
0.8214	Intermediate Similarity	NPC50305
0.8214	Intermediate Similarity	NPC471354
0.8214	Intermediate Similarity	NPC244402
0.8214	Intermediate Similarity	NPC243196
0.8214	Intermediate Similarity	NPC93883
0.8214	Intermediate Similarity	NPC77319
0.8214	Intermediate Similarity	NPC471353
0.8214	Intermediate Similarity	NPC27507
0.8214	Intermediate Similarity	NPC99728
0.8214	Intermediate Similarity	NPC471351
0.8208	Intermediate Similarity	NPC470768
0.8198	Intermediate Similarity	NPC84949
0.8198	Intermediate Similarity	NPC31354
0.8198	Intermediate Similarity	NPC471633
0.8198	Intermediate Similarity	NPC475163
0.8198	Intermediate Similarity	NPC69576
0.819	Intermediate Similarity	NPC11956
0.819	Intermediate Similarity	NPC472552
0.819	Intermediate Similarity	NPC472815
0.8182	Intermediate Similarity	NPC473125
0.8174	Intermediate Similarity	NPC196130
0.8174	Intermediate Similarity	NPC471082
0.8173	Intermediate Similarity	NPC473204
0.8173	Intermediate Similarity	NPC477721
0.8173	Intermediate Similarity	NPC477716
0.8165	Intermediate Similarity	NPC83005
0.8158	Intermediate Similarity	NPC470312
0.8158	Intermediate Similarity	NPC48692
0.8158	Intermediate Similarity	NPC476127
0.8158	Intermediate Similarity	NPC476150
0.8155	Intermediate Similarity	NPC98112
0.8155	Intermediate Similarity	NPC240372
0.8148	Intermediate Similarity	NPC38948
0.8142	Intermediate Similarity	NPC218093
0.8142	Intermediate Similarity	NPC470515
0.8142	Intermediate Similarity	NPC83287
0.8131	Intermediate Similarity	NPC470767
0.8131	Intermediate Similarity	NPC470763
0.8131	Intermediate Similarity	NPC51719
0.8119	Intermediate Similarity	NPC67398
0.8119	Intermediate Similarity	NPC474792
0.8119	Intermediate Similarity	NPC91654
0.8119	Intermediate Similarity	NPC474835
0.8113	Intermediate Similarity	NPC45897
0.8108	Intermediate Similarity	NPC293658
0.8108	Intermediate Similarity	NPC474410
0.8108	Intermediate Similarity	NPC49413
0.8108	Intermediate Similarity	NPC290608
0.8108	Intermediate Similarity	NPC40133
0.8108	Intermediate Similarity	NPC44298
0.8108	Intermediate Similarity	NPC75167
0.8108	Intermediate Similarity	NPC311592
0.8108	Intermediate Similarity	NPC473128
0.8103	Intermediate Similarity	NPC41129
0.81	Intermediate Similarity	NPC202886
0.8095	Intermediate Similarity	NPC472554
0.8077	Intermediate Similarity	NPC40182
0.8077	Intermediate Similarity	NPC318917
0.8077	Intermediate Similarity	NPC472186
0.8077	Intermediate Similarity	NPC471366
0.8077	Intermediate Similarity	NPC198422
0.8077	Intermediate Similarity	NPC476800
0.807	Intermediate Similarity	NPC470915
0.807	Intermediate Similarity	NPC81222
0.807	Intermediate Similarity	NPC5883
0.807	Intermediate Similarity	NPC55532
0.807	Intermediate Similarity	NPC236973
0.807	Intermediate Similarity	NPC470897
0.807	Intermediate Similarity	NPC470911
0.807	Intermediate Similarity	NPC29639
0.807	Intermediate Similarity	NPC470517
0.807	Intermediate Similarity	NPC30483
0.807	Intermediate Similarity	NPC32177
0.807	Intermediate Similarity	NPC291820
0.807	Intermediate Similarity	NPC469756
0.807	Intermediate Similarity	NPC44899
0.807	Intermediate Similarity	NPC304260
0.807	Intermediate Similarity	NPC292467
0.807	Intermediate Similarity	NPC329905
0.8058	Intermediate Similarity	NPC143446
0.8058	Intermediate Similarity	NPC171598
0.8056	Intermediate Similarity	NPC122816
0.8056	Intermediate Similarity	NPC471205
0.8056	Intermediate Similarity	NPC293512
0.8056	Intermediate Similarity	NPC475074
0.8053	Intermediate Similarity	NPC290693
0.8039	Intermediate Similarity	NPC2003
0.8039	Intermediate Similarity	NPC96736
0.8039	Intermediate Similarity	NPC25701
0.8039	Intermediate Similarity	NPC178949
0.8039	Intermediate Similarity	NPC211238
0.8036	Intermediate Similarity	NPC181145
0.802	Intermediate Similarity	NPC477749
0.8019	Intermediate Similarity	NPC150463
0.8019	Intermediate Similarity	NPC154452
0.8018	Intermediate Similarity	NPC231797
0.8	Intermediate Similarity	NPC476766
0.8	Intermediate Similarity	NPC475629
0.8	Intermediate Similarity	NPC72260
0.8	Intermediate Similarity	NPC324841
0.8	Intermediate Similarity	NPC475556

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 NPC82251 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	175
0.1-0.2	1244
0.2-0.3	3652
0.3-0.4	2554
0.4-0.5	1010
0.5-0.6	310
0.6-0.7	178
0.7-0.8	26
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
0.8667	High Similarity	NPD6686	Approved
0.8246	Intermediate Similarity	NPD7503	Approved
0.8142	Intermediate Similarity	NPD7328	Approved
0.8142	Intermediate Similarity	NPD7327	Approved
0.807	Intermediate Similarity	NPD7516	Approved
0.8	Intermediate Similarity	NPD8294	Approved
0.8	Intermediate Similarity	NPD8377	Approved
0.7931	Intermediate Similarity	NPD8378	Approved
0.7931	Intermediate Similarity	NPD8033	Approved
0.7931	Intermediate Similarity	NPD8335	Approved
0.7931	Intermediate Similarity	NPD8296	Approved
0.7931	Intermediate Similarity	NPD8380	Approved
0.7931	Intermediate Similarity	NPD8379	Approved
0.7815	Intermediate Similarity	NPD7507	Approved
0.7623	Intermediate Similarity	NPD7319	Approved
0.7573	Intermediate Similarity	NPD7838	Discovery
0.757	Intermediate Similarity	NPD8029	Clinical (unspecified phase)
0.7568	Intermediate Similarity	NPD6412	Phase 2
0.7479	Intermediate Similarity	NPD8513	Phase 3
0.7479	Intermediate Similarity	NPD8516	Approved
0.7479	Intermediate Similarity	NPD8515	Approved
0.7479	Intermediate Similarity	NPD8517	Approved
0.7434	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.7407	Intermediate Similarity	NPD7638	Approved
0.7407	Intermediate Similarity	NPD4225	Approved
0.7339	Intermediate Similarity	NPD7640	Approved
0.7339	Intermediate Similarity	NPD7639	Approved
0.7328	Intermediate Similarity	NPD8133	Approved
0.7327	Intermediate Similarity	NPD6400	Clinical (unspecified phase)
0.7281	Intermediate Similarity	NPD8132	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD5344	Discontinued
0.7238	Intermediate Similarity	NPD46	Approved
0.7238	Intermediate Similarity	NPD6698	Approved
0.7217	Intermediate Similarity	NPD5955	Clinical (unspecified phase)
0.7213	Intermediate Similarity	NPD8328	Phase 3
0.7182	Intermediate Similarity	NPD6648	Approved
0.7009	Intermediate Similarity	NPD8413	Clinical (unspecified phase)
0.6957	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6905	Remote Similarity	NPD8074	Phase 3
0.686	Remote Similarity	NPD7115	Discovery
0.686	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.686	Remote Similarity	NPD6009	Approved
0.6855	Remote Similarity	NPD6370	Approved
0.6852	Remote Similarity	NPD6411	Approved
0.6852	Remote Similarity	NPD7637	Suspended
0.685	Remote Similarity	NPD7736	Approved
0.6829	Remote Similarity	NPD6319	Approved
0.6807	Remote Similarity	NPD6882	Approved
0.6789	Remote Similarity	NPD5779	Approved
0.6789	Remote Similarity	NPD5778	Approved
0.6772	Remote Similarity	NPD8293	Discontinued
0.6754	Remote Similarity	NPD7632	Discontinued
0.675	Remote Similarity	NPD4632	Approved
0.6746	Remote Similarity	NPD7492	Approved
0.6697	Remote Similarity	NPD7983	Approved
0.6694	Remote Similarity	NPD6054	Approved
0.6693	Remote Similarity	NPD6616	Approved
0.6667	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6101	Approved
0.6667	Remote Similarity	NPD7830	Approved
0.6667	Remote Similarity	NPD8297	Approved
0.6667	Remote Similarity	NPD7829	Approved
0.6641	Remote Similarity	NPD7078	Approved
0.664	Remote Similarity	NPD6016	Approved
0.664	Remote Similarity	NPD6015	Approved
0.6636	Remote Similarity	NPD7524	Approved
0.6635	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.661	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6587	Remote Similarity	NPD5988	Approved
0.656	Remote Similarity	NPD6059	Approved
0.6535	Remote Similarity	NPD6067	Discontinued
0.6525	Remote Similarity	NPD5697	Approved
0.6509	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.65	Remote Similarity	NPD6371	Approved
0.65	Remote Similarity	NPD7625	Phase 1
0.6471	Remote Similarity	NPD6899	Approved
0.6471	Remote Similarity	NPD6881	Approved
0.6449	Remote Similarity	NPD1694	Approved
0.6446	Remote Similarity	NPD6649	Approved
0.6446	Remote Similarity	NPD6650	Approved
0.6444	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.6441	Remote Similarity	NPD6675	Approved
0.6441	Remote Similarity	NPD7128	Approved
0.6441	Remote Similarity	NPD6402	Approved
0.6441	Remote Similarity	NPD5739	Approved
0.6439	Remote Similarity	NPD7260	Phase 2
0.6434	Remote Similarity	NPD8451	Approved
0.6429	Remote Similarity	NPD7748	Approved
0.6417	Remote Similarity	NPD6373	Approved
0.6417	Remote Similarity	NPD6012	Approved
0.6417	Remote Similarity	NPD6013	Approved
0.6417	Remote Similarity	NPD6372	Approved
0.6417	Remote Similarity	NPD6014	Approved
0.6415	Remote Similarity	NPD6695	Phase 3
0.6404	Remote Similarity	NPD7902	Approved
0.64	Remote Similarity	NPD7641	Discontinued
0.6396	Remote Similarity	NPD7515	Phase 2
0.6393	Remote Similarity	NPD6053	Discontinued
0.6387	Remote Similarity	NPD5701	Approved
0.6387	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6385	Remote Similarity	NPD8448	Approved
0.6378	Remote Similarity	NPD8444	Approved
0.6378	Remote Similarity	NPD5983	Phase 2
0.6364	Remote Similarity	NPD8391	Approved
0.6364	Remote Similarity	NPD7102	Approved
0.6364	Remote Similarity	NPD8392	Approved
0.6364	Remote Similarity	NPD7290	Approved
0.6364	Remote Similarity	NPD6883	Approved
0.6364	Remote Similarity	NPD8390	Approved
0.6339	Remote Similarity	NPD6399	Phase 3
0.6333	Remote Similarity	NPD6011	Approved
0.6333	Remote Similarity	NPD7320	Approved
0.6316	Remote Similarity	NPD7839	Suspended
0.6311	Remote Similarity	NPD6617	Approved
0.6311	Remote Similarity	NPD6869	Approved
0.6311	Remote Similarity	NPD8130	Phase 1
0.6311	Remote Similarity	NPD6847	Approved
0.6279	Remote Similarity	NPD7604	Phase 2
0.6261	Remote Similarity	NPD6083	Phase 2
0.6261	Remote Similarity	NPD6084	Phase 2
0.625	Remote Similarity	NPD5281	Approved
0.625	Remote Similarity	NPD5284	Approved
0.6239	Remote Similarity	NPD5279	Phase 3
0.6239	Remote Similarity	NPD3618	Phase 1
0.6231	Remote Similarity	NPD8342	Approved
0.6231	Remote Similarity	NPD8299	Approved
0.6231	Remote Similarity	NPD8341	Approved
0.6231	Remote Similarity	NPD8340	Approved
0.623	Remote Similarity	NPD4634	Approved
0.6228	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6228	Remote Similarity	NPD5695	Phase 3
0.6216	Remote Similarity	NPD6051	Approved
0.6202	Remote Similarity	NPD5126	Approved
0.6202	Remote Similarity	NPD5125	Phase 3
0.619	Remote Similarity	NPD7505	Discontinued
0.619	Remote Similarity	NPD6929	Approved
0.6186	Remote Similarity	NPD5211	Phase 2
0.6183	Remote Similarity	NPD6336	Discontinued
0.6182	Remote Similarity	NPD7750	Discontinued
0.617	Remote Similarity	NPD7266	Discontinued
0.6168	Remote Similarity	NPD5209	Approved
0.6167	Remote Similarity	NPD6008	Approved
0.6154	Remote Similarity	NPD7642	Approved
0.6154	Remote Similarity	NPD5286	Approved
0.6154	Remote Similarity	NPD5285	Approved
0.6154	Remote Similarity	NPD4696	Approved
0.614	Remote Similarity	NPD7900	Approved
0.614	Remote Similarity	NPD5282	Discontinued
0.614	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6132	Remote Similarity	NPD6931	Approved
0.6132	Remote Similarity	NPD6930	Phase 2
0.6132	Remote Similarity	NPD7332	Phase 2
0.6132	Remote Similarity	NPD7514	Phase 3
0.6124	Remote Similarity	NPD6921	Approved
0.6121	Remote Similarity	NPD4755	Approved
0.6117	Remote Similarity	NPD8264	Approved
0.6117	Remote Similarity	NPD8039	Approved
0.6111	Remote Similarity	NPD3670	Clinical (unspecified phase)
0.6111	Remote Similarity	NPD3669	Approved
0.6106	Remote Similarity	NPD6079	Approved
0.6095	Remote Similarity	NPD7145	Approved
0.6091	Remote Similarity	NPD7521	Approved
0.6091	Remote Similarity	NPD4249	Approved
0.6091	Remote Similarity	NPD7334	Approved
0.6091	Remote Similarity	NPD6409	Approved
0.6091	Remote Similarity	NPD5330	Approved
0.6091	Remote Similarity	NPD7146	Approved
0.6091	Remote Similarity	NPD6684	Approved
0.609	Remote Similarity	NPD6033	Approved
0.6083	Remote Similarity	NPD5141	Approved
0.6075	Remote Similarity	NPD6902	Approved
0.6071	Remote Similarity	NPD5328	Approved
0.6068	Remote Similarity	NPD5696	Approved
0.6058	Remote Similarity	NPD6933	Approved
0.6055	Remote Similarity	NPD3666	Approved
0.6055	Remote Similarity	NPD3133	Approved
0.6055	Remote Similarity	NPD3665	Phase 1
0.6053	Remote Similarity	NPD8171	Discontinued
0.6053	Remote Similarity	NPD4202	Approved
0.605	Remote Similarity	NPD5226	Approved
0.605	Remote Similarity	NPD5224	Approved
0.605	Remote Similarity	NPD5225	Approved
0.605	Remote Similarity	NPD4633	Approved
0.6048	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6038	Remote Similarity	NPD7645	Phase 2
0.6036	Remote Similarity	NPD3573	Approved
0.6036	Remote Similarity	NPD4250	Approved
0.6036	Remote Similarity	NPD4251	Approved
0.6034	Remote Similarity	NPD5221	Approved
0.6034	Remote Similarity	NPD5222	Approved
0.6034	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6033	Remote Similarity	NPD6640	Phase 3
0.6029	Remote Similarity	NPD8338	Approved
0.6029	Remote Similarity	NPD6845	Suspended
0.6019	Remote Similarity	NPD3667	Approved
0.6018	Remote Similarity	NPD3168	Discontinued
0.6018	Remote Similarity	NPD5785	Approved
0.6017	Remote Similarity	NPD4700	Approved
0.6	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6	Remote Similarity	NPD6932	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