NPASS Compound

Structure

NPC280991 OpenBabel07101718312D 36 38 0 0 1 0 0 0 0 0999 V2000 -1.1340 3.2321 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.4641 2.7321 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5000 -0.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0000 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.4641 -1.2679 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.9641 -2.1340 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5000 2.5981 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7321 0.7321 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1340 2.2321 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7321 -1.2679 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7321 1.7321 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5981 -1.7679 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7321 -0.2679 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8660 1.2321 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.3301 0.2321 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.4641 1.7321 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0000 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.0000 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5981 1.2321 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.3301 1.2321 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.4641 -0.2679 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.0000 1.7321 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0000 1.7321 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.5000 0.8660 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.5000 0.8660 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.4641 -1.2679 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0000 1.7321 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.5981 0.2321 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.5000 -0.8660 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.5000 2.5981 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.5000 2.5981 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.0622 1.2321 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 2.5000 0.8660 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.5000 0.8660 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.1962 1.7321 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 9 2 0 0 0 0 2 16 1 0 0 0 0 4 18 1 0 0 0 0 5 26 1 0 0 0 0 6 26 1 0 0 0 0 9 27 1 0 0 0 0 10 12 1 0 0 0 0 10 13 1 0 0 0 0 11 14 1 0 0 0 0 11 19 1 0 0 0 0 12 26 1 0 0 0 0 13 28 1 0 0 0 0 14 27 1 0 0 0 0 15 20 1 0 0 0 0 15 21 1 0 0 0 0 16 19 2 0 0 0 0 16 20 1 0 0 0 0 17 3 1 6 0 0 0 17 24 1 0 0 0 0 17 33 1 0 0 0 0 18 29 2 0 0 0 0 18 34 1 0 0 0 0 19 28 1 0 0 0 0 20 36 1 1 0 0 0 21 26 1 0 0 0 0 21 28 1 6 0 0 0 22 23 1 0 0 0 0 22 24 1 0 0 0 0 22 30 1 1 0 0 0 23 25 1 0 0 0 0 23 31 1 6 0 0 0 24 34 1 6 0 0 0 25 33 1 0 0 0 0 25 35 1 1 0 0 0 27 7 1 1 0 0 0 27 35 1 0 0 0 0 28 8 1 6 0 0 0 32 36 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	510.32
Volume:	529.587
LogP:	3.805
LogD:	2.971
LogS:	-4.158
# Rotatable Bonds:	9
TPSA:	114.68
# H-Bond Aceptor:	8
# H-Bond Donor:	3
# Rings:	3
# Heavy Atoms:	8

MedChem Properties

QED Drug-Likeness Score:	0.189
Synthetic Accessibility Score:	5.242
Fsp3:	0.821
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.916
MDCK Permeability:	1.5718173017376103e-05
Pgp-inhibitor:	0.998
Pgp-substrate:	0.907
Human Intestinal Absorption (HIA):	0.093
20% Bioavailability (F20%):	0.007
30% Bioavailability (F30%):	0.09

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.02
Plasma Protein Binding (PPB):	93.64640045166016%
Volume Distribution (VD):	2.096
Pgp-substrate:	6.975322246551514%

ADMET: Metabolism

CYP1A2-inhibitor:	0.015
CYP1A2-substrate:	0.42
CYP2C19-inhibitor:	0.016
CYP2C19-substrate:	0.85
CYP2C9-inhibitor:	0.105
CYP2C9-substrate:	0.15
CYP2D6-inhibitor:	0.025
CYP2D6-substrate:	0.156
CYP3A4-inhibitor:	0.618
CYP3A4-substrate:	0.316

ADMET: Excretion

Clearance (CL):	1.65
Half-life (T1/2):	0.297

ADMET: Toxicity

hERG Blockers:	0.118
Human Hepatotoxicity (H-HT):	0.368
Drug-inuced Liver Injury (DILI):	0.235
AMES Toxicity:	0.479
Rat Oral Acute Toxicity:	0.193
Maximum Recommended Daily Dose:	0.082
Skin Sensitization:	0.353
Carcinogencity:	0.29
Eye Corrosion:	0.131
Eye Irritation:	0.037
Respiratory Toxicity:	0.969

Download Data

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

Natural Product: NPC280991

Natural Product ID:	NPC280991
*Common Name:**	7Alpha-Hydroperoxylabda-8,14-Dien-13(R)-Ol-4-O-Acetyl-Alpha-L-6-Deoxyidopyranoside
IUPAC Name:	[(2S,3S,4R,5R,6S)-6-[(3R)-5-[(3R,4aS,8aS)-3-hydroperoxy-2,5,5,8a-tetramethyl-3,4,4a,6,7,8-hexahydronaphthalen-1-yl]-3-methylpent-1-en-3-yl]oxy-4,5-dihydroxy-2-methyloxan-3-yl] acetate
Synonyms:
Standard InCHIKey:	CYFQGASFWKNUEE-PEJODWCSSA-N
Standard InCHI:	InChI=1S/C28H46O8/c1-9-27(7,35-25-23(31)22(30)24(17(3)33-25)34-18(4)29)14-11-19-16(2)20(36-32)15-21-26(5,6)12-10-13-28(19,21)8/h9,17,20-25,30-32H,1,10-15H2,2-8H3/t17-,20+,21-,22+,23+,24+,25-,27-,28+/m0/s1
SMILES:	OO[C@@H]1C[C@H]2C(C)(C)CCC[C@@]2(C(=C1C)CC[C@@](O[C@@H]1O[C@@H](C)[C@H]([C@@H]([C@H]1O)O)OC(=O)C)(C=C)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL483433
PubChem CID:	11049491
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001551] Diterpenoids

*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
NPO16949	Aster oharai	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12193011]
NPO16949	Aster oharai	Species	Asteraceae	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
ED50	8

Activity Type	# Activity
Cell Line	8

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT390	Cell Line	LOX IMVI	Homo sapiens	ED50	>	10.0	ug ml-1	PMID[478594]
NPT147	Cell Line	SK-MEL-2	Homo sapiens	ED50	>	10.0	ug ml-1	PMID[478594]
NPT383	Cell Line	SNB-19	Homo sapiens	ED50	>	10.0	ug ml-1	PMID[478594]
NPT380	Cell Line	U-251	Homo sapiens	ED50	>	10.0	ug ml-1	PMID[478594]
NPT323	Cell Line	SW-620	Homo sapiens	ED50	>	10.0	ug ml-1	PMID[478594]
NPT148	Cell Line	HCT-15	Homo sapiens	ED50	>	10.0	ug ml-1	PMID[478594]
NPT81	Cell Line	A549	Homo sapiens	ED50	>	10.0	ug ml-1	PMID[478594]
NPT146	Cell Line	SK-OV-3	Homo sapiens	ED50	>	10.0	ug ml-1	PMID[478594]

☑ 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 NPC280991 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	215
0.1-0.2	1439
0.2-0.3	4631
0.3-0.4	10657
0.4-0.5	11111
0.5-0.6	7423
0.6-0.7	5264
0.7-0.8	1842
0.8-0.85	95
0.85-0.9	10
0.9-0.95	3
0.95-1	7

Similarity Score	Similarity Level	Natural Product ID
0.9468	High Similarity	NPC91197
0.9468	High Similarity	NPC309503
0.9468	High Similarity	NPC239547
0.9468	High Similarity	NPC155319
0.9468	High Similarity	NPC96597
0.9468	High Similarity	NPC125551
0.9043	High Similarity	NPC67398
0.9043	High Similarity	NPC91654
0.9043	High Similarity	NPC474792
0.8842	High Similarity	NPC474835
0.8812	High Similarity	NPC470767
0.8812	High Similarity	NPC470763
0.875	High Similarity	NPC178949
0.875	High Similarity	NPC96736
0.8737	High Similarity	NPC302584
0.8725	High Similarity	NPC472390
0.8713	High Similarity	NPC470768
0.87	High Similarity	NPC470571
0.8667	High Similarity	NPC473125
0.8641	High Similarity	NPC135015
0.8641	High Similarity	NPC48548
0.8641	High Similarity	NPC128795
0.8641	High Similarity	NPC217921
0.8586	High Similarity	NPC477928
0.8585	High Similarity	NPC473159
0.8585	High Similarity	NPC44298
0.8585	High Similarity	NPC40133
0.8585	High Similarity	NPC290608
0.8585	High Similarity	NPC49413
0.8585	High Similarity	NPC473128
0.8571	High Similarity	NPC90583
0.8558	High Similarity	NPC316974
0.8558	High Similarity	NPC40728
0.8557	High Similarity	NPC211238
0.8544	High Similarity	NPC125423
0.8544	High Similarity	NPC33053
0.8544	High Similarity	NPC88013
0.8485	Intermediate Similarity	NPC240372
0.8476	Intermediate Similarity	NPC83005
0.8469	Intermediate Similarity	NPC286612
0.8469	Intermediate Similarity	NPC275310
0.8469	Intermediate Similarity	NPC230347
0.8462	Intermediate Similarity	NPC311223
0.8447	Intermediate Similarity	NPC239961
0.8447	Intermediate Similarity	NPC82251
0.8438	Intermediate Similarity	NPC261990
0.8438	Intermediate Similarity	NPC474249
0.8438	Intermediate Similarity	NPC202886
0.8431	Intermediate Similarity	NPC127933
0.8431	Intermediate Similarity	NPC473123
0.8431	Intermediate Similarity	NPC7644
0.8431	Intermediate Similarity	NPC473124
0.8431	Intermediate Similarity	NPC7613
0.8431	Intermediate Similarity	NPC475889
0.8421	Intermediate Similarity	NPC248312
0.8416	Intermediate Similarity	NPC285231
0.8416	Intermediate Similarity	NPC154127
0.8416	Intermediate Similarity	NPC21568
0.8416	Intermediate Similarity	NPC198992
0.8411	Intermediate Similarity	NPC75167
0.8411	Intermediate Similarity	NPC470027
0.8411	Intermediate Similarity	NPC311592
0.8396	Intermediate Similarity	NPC470026
0.8387	Intermediate Similarity	NPC166279
0.8367	Intermediate Similarity	NPC305160
0.835	Intermediate Similarity	NPC201880
0.835	Intermediate Similarity	NPC473207
0.835	Intermediate Similarity	NPC81567
0.835	Intermediate Similarity	NPC203354
0.835	Intermediate Similarity	NPC173583
0.835	Intermediate Similarity	NPC264867
0.835	Intermediate Similarity	NPC110656
0.835	Intermediate Similarity	NPC470321
0.835	Intermediate Similarity	NPC93352
0.835	Intermediate Similarity	NPC473127
0.8349	Intermediate Similarity	NPC203862
0.8333	Intermediate Similarity	NPC181145
0.8333	Intermediate Similarity	NPC477748
0.8333	Intermediate Similarity	NPC121423
0.8333	Intermediate Similarity	NPC238397
0.8333	Intermediate Similarity	NPC154452
0.8333	Intermediate Similarity	NPC309310
0.8333	Intermediate Similarity	NPC471363
0.8318	Intermediate Similarity	NPC328074
0.8318	Intermediate Similarity	NPC321272
0.8318	Intermediate Similarity	NPC317460
0.8318	Intermediate Similarity	NPC470025
0.8317	Intermediate Similarity	NPC64348
0.8302	Intermediate Similarity	NPC316708
0.8302	Intermediate Similarity	NPC170974
0.8302	Intermediate Similarity	NPC103627
0.8302	Intermediate Similarity	NPC119550
0.8302	Intermediate Similarity	NPC191439
0.83	Intermediate Similarity	NPC98112
0.8286	Intermediate Similarity	NPC219900
0.8286	Intermediate Similarity	NPC38376
0.8286	Intermediate Similarity	NPC224660
0.8286	Intermediate Similarity	NPC80210
0.8286	Intermediate Similarity	NPC177524
0.8286	Intermediate Similarity	NPC392
0.8269	Intermediate Similarity	NPC473199
0.8257	Intermediate Similarity	NPC199428
0.8257	Intermediate Similarity	NPC207637
0.8257	Intermediate Similarity	NPC99620
0.8257	Intermediate Similarity	NPC5311
0.8257	Intermediate Similarity	NPC310341
0.8257	Intermediate Similarity	NPC193382
0.8252	Intermediate Similarity	NPC134270
0.8252	Intermediate Similarity	NPC281378
0.8241	Intermediate Similarity	NPC293658
0.8241	Intermediate Similarity	NPC474410
0.8235	Intermediate Similarity	NPC11974
0.8235	Intermediate Similarity	NPC121072
0.8235	Intermediate Similarity	NPC477717
0.8235	Intermediate Similarity	NPC21064
0.8224	Intermediate Similarity	NPC17791
0.8218	Intermediate Similarity	NPC312325
0.8208	Intermediate Similarity	NPC195116
0.8208	Intermediate Similarity	NPC285253
0.8208	Intermediate Similarity	NPC473328
0.8208	Intermediate Similarity	NPC206618
0.8208	Intermediate Similarity	NPC473318
0.8208	Intermediate Similarity	NPC221110
0.8208	Intermediate Similarity	NPC180459
0.8208	Intermediate Similarity	NPC28844
0.82	Intermediate Similarity	NPC129569
0.82	Intermediate Similarity	NPC171598
0.8198	Intermediate Similarity	NPC477071
0.819	Intermediate Similarity	NPC184512
0.819	Intermediate Similarity	NPC293512
0.819	Intermediate Similarity	NPC281939
0.819	Intermediate Similarity	NPC109376
0.819	Intermediate Similarity	NPC122816
0.8182	Intermediate Similarity	NPC87250
0.8182	Intermediate Similarity	NPC142066
0.8182	Intermediate Similarity	NPC157376
0.8182	Intermediate Similarity	NPC471353
0.8182	Intermediate Similarity	NPC158344
0.8182	Intermediate Similarity	NPC473852
0.8182	Intermediate Similarity	NPC309034
0.8182	Intermediate Similarity	NPC243196
0.8182	Intermediate Similarity	NPC474418
0.8182	Intermediate Similarity	NPC473405
0.8182	Intermediate Similarity	NPC196429
0.8182	Intermediate Similarity	NPC72817
0.8182	Intermediate Similarity	NPC244402
0.8182	Intermediate Similarity	NPC471351
0.8182	Intermediate Similarity	NPC99728
0.8182	Intermediate Similarity	NPC50305
0.8182	Intermediate Similarity	NPC34390
0.8182	Intermediate Similarity	NPC477927
0.8182	Intermediate Similarity	NPC471355
0.8182	Intermediate Similarity	NPC77319
0.8182	Intermediate Similarity	NPC84987
0.8182	Intermediate Similarity	NPC93883
0.8182	Intermediate Similarity	NPC471354
0.8182	Intermediate Similarity	NPC27507
0.8182	Intermediate Similarity	NPC152615
0.8173	Intermediate Similarity	NPC85593
0.8173	Intermediate Similarity	NPC31430
0.8165	Intermediate Similarity	NPC69576
0.8165	Intermediate Similarity	NPC471633
0.8165	Intermediate Similarity	NPC220293
0.8165	Intermediate Similarity	NPC84949
0.8165	Intermediate Similarity	NPC31354
0.8163	Intermediate Similarity	NPC289361
0.8163	Intermediate Similarity	NPC477749
0.8155	Intermediate Similarity	NPC150463
0.8155	Intermediate Similarity	NPC214277
0.8155	Intermediate Similarity	NPC201191
0.8148	Intermediate Similarity	NPC216595
0.8148	Intermediate Similarity	NPC473567
0.8148	Intermediate Similarity	NPC231797
0.8148	Intermediate Similarity	NPC174836
0.8144	Intermediate Similarity	NPC473058
0.8137	Intermediate Similarity	NPC477968
0.8137	Intermediate Similarity	NPC161527
0.8137	Intermediate Similarity	NPC228251
0.8137	Intermediate Similarity	NPC477721
0.8137	Intermediate Similarity	NPC477716
0.8137	Intermediate Similarity	NPC477972
0.8137	Intermediate Similarity	NPC219285
0.8137	Intermediate Similarity	NPC20113
0.8137	Intermediate Similarity	NPC477971
0.8131	Intermediate Similarity	NPC177047
0.8131	Intermediate Similarity	NPC65155
0.8125	Intermediate Similarity	NPC48692
0.8125	Intermediate Similarity	NPC135369
0.8119	Intermediate Similarity	NPC473244
0.8113	Intermediate Similarity	NPC472988
0.8113	Intermediate Similarity	NPC38948
0.8113	Intermediate Similarity	NPC470024
0.8113	Intermediate Similarity	NPC38217
0.8108	Intermediate Similarity	NPC218093
0.8108	Intermediate Similarity	NPC470515
0.8108	Intermediate Similarity	NPC471548
0.8108	Intermediate Similarity	NPC45475
0.8108	Intermediate Similarity	NPC83287
0.81	Intermediate Similarity	NPC472189
0.81	Intermediate Similarity	NPC471362

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 NPC280991 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	183
0.1-0.2	1653
0.2-0.3	3897
0.3-0.4	2207
0.4-0.5	752
0.5-0.6	303
0.6-0.7	137
0.7-0.8	17
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8286	Intermediate Similarity	NPD6686	Approved
0.8214	Intermediate Similarity	NPD7503	Approved
0.8108	Intermediate Similarity	NPD7327	Approved
0.8108	Intermediate Similarity	NPD7328	Approved
0.8036	Intermediate Similarity	NPD7516	Approved
0.7965	Intermediate Similarity	NPD8377	Approved
0.7965	Intermediate Similarity	NPD8294	Approved
0.7895	Intermediate Similarity	NPD8380	Approved
0.7895	Intermediate Similarity	NPD8033	Approved
0.7895	Intermediate Similarity	NPD8379	Approved
0.7895	Intermediate Similarity	NPD8378	Approved
0.7895	Intermediate Similarity	NPD8296	Approved
0.7895	Intermediate Similarity	NPD8335	Approved
0.7706	Intermediate Similarity	NPD8132	Clinical (unspecified phase)
0.7627	Intermediate Similarity	NPD7507	Approved
0.7523	Intermediate Similarity	NPD6412	Phase 2
0.7438	Intermediate Similarity	NPD7319	Approved
0.7434	Intermediate Similarity	NPD8133	Approved
0.7288	Intermediate Similarity	NPD8513	Phase 3
0.7288	Intermediate Similarity	NPD8516	Approved
0.7288	Intermediate Similarity	NPD8517	Approved
0.7288	Intermediate Similarity	NPD8515	Approved
0.7241	Intermediate Similarity	NPD8295	Clinical (unspecified phase)
0.7232	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD5344	Discontinued
0.7196	Intermediate Similarity	NPD8029	Clinical (unspecified phase)
0.7196	Intermediate Similarity	NPD7638	Approved
0.7167	Intermediate Similarity	NPD8328	Phase 3
0.7143	Intermediate Similarity	NPD5345	Clinical (unspecified phase)
0.713	Intermediate Similarity	NPD7639	Approved
0.713	Intermediate Similarity	NPD7640	Approved
0.7105	Intermediate Similarity	NPD8413	Clinical (unspecified phase)
0.7019	Intermediate Similarity	NPD7838	Discovery
0.7019	Intermediate Similarity	NPD46	Approved
0.7019	Intermediate Similarity	NPD6698	Approved
0.7018	Intermediate Similarity	NPD5955	Clinical (unspecified phase)
0.6931	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6881	Remote Similarity	NPD4225	Approved
0.6832	Remote Similarity	NPD3669	Approved
0.6832	Remote Similarity	NPD3670	Clinical (unspecified phase)
0.6818	Remote Similarity	NPD6648	Approved
0.6807	Remote Similarity	NPD7115	Discovery
0.6803	Remote Similarity	NPD6370	Approved
0.68	Remote Similarity	NPD7736	Approved
0.6762	Remote Similarity	NPD6051	Approved
0.6754	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6752	Remote Similarity	NPD6882	Approved
0.672	Remote Similarity	NPD8293	Discontinued
0.672	Remote Similarity	NPD8074	Phase 3
0.6696	Remote Similarity	NPD7632	Discontinued
0.6694	Remote Similarity	NPD7492	Approved
0.6667	Remote Similarity	NPD6009	Approved
0.664	Remote Similarity	NPD6616	Approved
0.6639	Remote Similarity	NPD6319	Approved
0.6639	Remote Similarity	NPD6054	Approved
0.661	Remote Similarity	NPD8297	Approved
0.6598	Remote Similarity	NPD1810	Approved
0.6598	Remote Similarity	NPD1811	Approved
0.6587	Remote Similarity	NPD7078	Approved
0.6585	Remote Similarity	NPD6921	Approved
0.6571	Remote Similarity	NPD7524	Approved
0.6555	Remote Similarity	NPD4632	Approved
0.6504	Remote Similarity	NPD6059	Approved
0.6481	Remote Similarity	NPD7983	Approved
0.6481	Remote Similarity	NPD6411	Approved
0.6481	Remote Similarity	NPD7637	Suspended
0.6471	Remote Similarity	NPD6053	Discontinued
0.6452	Remote Similarity	NPD6015	Approved
0.6452	Remote Similarity	NPD6016	Approved
0.6449	Remote Similarity	NPD7625	Phase 1
0.6442	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6436	Remote Similarity	NPD7645	Phase 2
0.6422	Remote Similarity	NPD6399	Phase 3
0.6422	Remote Similarity	NPD5779	Approved
0.6422	Remote Similarity	NPD5778	Approved
0.641	Remote Similarity	NPD6881	Approved
0.641	Remote Similarity	NPD6899	Approved
0.64	Remote Similarity	NPD5988	Approved
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
0.6373	Remote Similarity	NPD7525	Registered
0.6364	Remote Similarity	NPD7748	Approved
0.6356	Remote Similarity	NPD6373	Approved
0.6356	Remote Similarity	NPD6372	Approved
0.6349	Remote Similarity	NPD6067	Discontinued
0.6346	Remote Similarity	NPD6695	Phase 3
0.6339	Remote Similarity	NPD7902	Approved
0.6339	Remote Similarity	NPD6084	Phase 2
0.6339	Remote Similarity	NPD6083	Phase 2
0.633	Remote Similarity	NPD7515	Phase 2
0.6328	Remote Similarity	NPD8448	Approved
0.6325	Remote Similarity	NPD5697	Approved
0.6308	Remote Similarity	NPD8390	Approved
0.6308	Remote Similarity	NPD8391	Approved
0.6308	Remote Similarity	NPD8392	Approved
0.6303	Remote Similarity	NPD6883	Approved
0.6303	Remote Similarity	NPD7102	Approved
0.6303	Remote Similarity	NPD7290	Approved
0.6303	Remote Similarity	NPD6371	Approved
0.6296	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6296	Remote Similarity	NPD6101	Approved
0.6289	Remote Similarity	NPD2686	Approved
0.6289	Remote Similarity	NPD2687	Approved
0.6289	Remote Similarity	NPD2254	Approved
0.6273	Remote Similarity	NPD8171	Discontinued
0.6271	Remote Similarity	NPD7320	Approved
0.626	Remote Similarity	NPD7260	Phase 2
0.625	Remote Similarity	NPD6869	Approved
0.625	Remote Similarity	NPD8130	Phase 1
0.625	Remote Similarity	NPD6847	Approved
0.625	Remote Similarity	NPD6617	Approved
0.6226	Remote Similarity	NPD1694	Approved
0.622	Remote Similarity	NPD7829	Approved
0.622	Remote Similarity	NPD7604	Phase 2
0.622	Remote Similarity	NPD7642	Approved
0.622	Remote Similarity	NPD7830	Approved
0.6218	Remote Similarity	NPD6013	Approved
0.6218	Remote Similarity	NPD6014	Approved
0.6218	Remote Similarity	NPD6012	Approved
0.619	Remote Similarity	NPD8444	Approved
0.619	Remote Similarity	NPD5983	Phase 2
0.6186	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6186	Remote Similarity	NPD5701	Approved
0.6174	Remote Similarity	NPD4159	Approved
0.6172	Remote Similarity	NPD8340	Approved
0.6172	Remote Similarity	NPD8299	Approved
0.6172	Remote Similarity	NPD8341	Approved
0.6172	Remote Similarity	NPD8342	Approved
0.6161	Remote Similarity	NPD5695	Phase 3
0.6154	Remote Similarity	NPD1780	Approved
0.6154	Remote Similarity	NPD1779	Approved
0.6142	Remote Similarity	NPD5125	Phase 3
0.6142	Remote Similarity	NPD5126	Approved
0.6134	Remote Similarity	NPD6011	Approved
0.6124	Remote Similarity	NPD6336	Discontinued
0.6122	Remote Similarity	NPD7532	Clinical (unspecified phase)
0.6111	Remote Similarity	NPD7750	Discontinued
0.6111	Remote Similarity	NPD4751	Clinical (unspecified phase)
0.6106	Remote Similarity	NPD7839	Suspended
0.6095	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6091	Remote Similarity	NPD3168	Discontinued
0.609	Remote Similarity	NPD8449	Approved
0.6071	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6071	Remote Similarity	NPD7900	Approved
0.6058	Remote Similarity	NPD7332	Phase 2
0.6058	Remote Similarity	NPD6931	Approved
0.6058	Remote Similarity	NPD6930	Phase 2
0.6058	Remote Similarity	NPD7514	Phase 3
0.6045	Remote Similarity	NPD8450	Suspended
0.604	Remote Similarity	NPD6942	Approved
0.604	Remote Similarity	NPD7339	Approved
0.6033	Remote Similarity	NPD4634	Approved
0.6031	Remote Similarity	NPD6033	Approved
0.6029	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.6019	Remote Similarity	NPD7521	Approved
0.6019	Remote Similarity	NPD6409	Approved
0.6019	Remote Similarity	NPD6684	Approved
0.6019	Remote Similarity	NPD7334	Approved
0.6019	Remote Similarity	NPD7146	Approved
0.6019	Remote Similarity	NPD5330	Approved
0.6017	Remote Similarity	NPD8170	Clinical (unspecified phase)
0.6	Remote Similarity	NPD5696	Approved
0.6	Remote Similarity	NPD8137	Clinical (unspecified phase)
0.5984	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.5983	Remote Similarity	NPD5211	Phase 2
0.5981	Remote Similarity	NPD4786	Approved
0.598	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.598	Remote Similarity	NPD6933	Approved
0.597	Remote Similarity	NPD6845	Suspended
0.5966	Remote Similarity	NPD6008	Approved
0.5965	Remote Similarity	NPD4792	Clinical (unspecified phase)
0.5963	Remote Similarity	NPD4251	Approved
0.5963	Remote Similarity	NPD4250	Approved
0.5963	Remote Similarity	NPD3573	Approved
0.5962	Remote Similarity	NPD6929	Approved
0.5952	Remote Similarity	NPD7641	Discontinued
0.5948	Remote Similarity	NPD5286	Approved
0.5948	Remote Similarity	NPD5285	Approved
0.5948	Remote Similarity	NPD4696	Approved
0.5946	Remote Similarity	NPD8522	Clinical (unspecified phase)
0.5943	Remote Similarity	NPD3667	Approved
0.594	Remote Similarity	NPD5956	Approved
0.5926	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.5922	Remote Similarity	NPD6932	Approved
0.5913	Remote Similarity	NPD4755	Approved
0.5909	Remote Similarity	NPD6903	Approved
0.5909	Remote Similarity	NPD6672	Approved
0.5909	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.5909	Remote Similarity	NPD5737	Approved
0.5906	Remote Similarity	NPD7100	Approved
0.5906	Remote Similarity	NPD7101	Approved
0.5905	Remote Similarity	NPD4820	Approved
0.5905	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.5905	Remote Similarity	NPD4819	Approved
0.5905	Remote Similarity	NPD4822	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