NPASS Compound

Structure

NPC474835 OpenBabel07101719142D 34 36 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 -5.9641 -2.1340 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 -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 -6.3301 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 -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 -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 1 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 -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 1 9 2 0 0 0 0 2 17 2 0 0 0 0 4 19 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 14 1 0 0 0 0 10 15 1 0 0 0 0 11 12 1 0 0 0 0 11 17 1 0 0 0 0 12 21 1 0 0 0 0 13 16 1 0 0 0 0 13 20 1 0 0 0 0 14 26 1 0 0 0 0 15 28 1 0 0 0 0 16 27 1 0 0 0 0 17 20 1 0 0 0 0 18 3 1 6 0 0 0 18 24 1 0 0 0 0 18 32 1 0 0 0 0 19 29 2 0 0 0 0 19 33 1 0 0 0 0 20 28 1 6 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 33 1 6 0 0 0 25 32 1 0 0 0 0 25 34 1 1 0 0 0 27 7 1 1 0 0 0 27 34 1 0 0 0 0 28 8 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	478.33
Volume:	512.007
LogP:	4.83
LogD:	3.765
LogS:	-5.127
# Rotatable Bonds:	8
TPSA:	85.22
# H-Bond Aceptor:	6
# H-Bond Donor:	2
# Rings:	3
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.399
Synthetic Accessibility Score:	4.967
Fsp3:	0.821
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:	-4.688
MDCK Permeability:	1.9031429474125616e-05
Pgp-inhibitor:	0.998
Pgp-substrate:	0.091
Human Intestinal Absorption (HIA):	0.013
20% Bioavailability (F20%):	0.006
30% Bioavailability (F30%):	0.01

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.092
Plasma Protein Binding (PPB):	85.48563385009766%
Volume Distribution (VD):	1.939
Pgp-substrate:	13.23405933380127%

ADMET: Metabolism

CYP1A2-inhibitor:	0.02
CYP1A2-substrate:	0.284
CYP2C19-inhibitor:	0.023
CYP2C19-substrate:	0.809
CYP2C9-inhibitor:	0.142
CYP2C9-substrate:	0.083
CYP2D6-inhibitor:	0.019
CYP2D6-substrate:	0.204
CYP3A4-inhibitor:	0.768
CYP3A4-substrate:	0.301

ADMET: Excretion

Clearance (CL):	1.923
Half-life (T1/2):	0.174

ADMET: Toxicity

hERG Blockers:	0.11
Human Hepatotoxicity (H-HT):	0.341
Drug-inuced Liver Injury (DILI):	0.301
AMES Toxicity:	0.02
Rat Oral Acute Toxicity:	0.367
Maximum Recommended Daily Dose:	0.067
Skin Sensitization:	0.305
Carcinogencity:	0.255
Eye Corrosion:	0.094
Eye Irritation:	0.032
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: NPC474835

Natural Product ID:	NPC474835
*Common Name:**	7Alpha-Hydroperoxylabda-8(17),14-Dien-13(R)-Ol-4-O-Acetyl-Alpha-L-6-Deoxyidopyranoside
IUPAC Name:	[(2S,3S,4R,5R,6S)-6-[(3R)-5-[(1S,4aS,8aS)-5,5,8a-trimethyl-2-methylidene-3,4,4a,6,7,8-hexahydro-1H-naphthalen-1-yl]-3-methylpent-1-en-3-yl]oxy-4,5-dihydroxy-2-methyloxan-3-yl] acetate
Synonyms:
Standard InCHIKey:	ZTNQJRLNKSLKMO-QQYBNUSVSA-N
Standard InCHI:	InChI=1S/C28H46O6/c1-9-27(7,34-25-23(31)22(30)24(18(3)32-25)33-19(4)29)16-13-20-17(2)11-12-21-26(5,6)14-10-15-28(20,21)8/h9,18,20-25,30-31H,1-2,10-16H2,3-8H3/t18-,20-,21-,22+,23+,24+,25-,27-,28+/m0/s1
SMILES:	C=C[C@](O[C@@H]1O[C@@H](C)[C@H]([C@@H]([C@H]1O)O)OC(=O)C)(CC[C@H]1C(=C)CC[C@@H]2[C@]1(C)CCCC2(C)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL484445
PubChem CID:	44575995
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	4

Activity Type	# Activity
Cell Line	4

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT148	Cell Line	HCT-15	Homo sapiens	ED50	=	1.1	ug ml-1	PMID[570024]
NPT390	Cell Line	LOX IMVI	Homo sapiens	ED50	=	1.5	ug ml-1	PMID[570024]
NPT147	Cell Line	SK-MEL-2	Homo sapiens	ED50	=	1.3	ug ml-1	PMID[570024]
NPT383	Cell Line	SNB-19	Homo sapiens	ED50	=	1.3	ug ml-1	PMID[570024]

☑ 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 NPC474835 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	227
0.1-0.2	1650
0.2-0.3	5105
0.3-0.4	12495
0.4-0.5	9692
0.5-0.6	6684
0.6-0.7	5200
0.7-0.8	1563
0.8-0.85	62
0.85-0.9	11
0.9-0.95	7
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9341	High Similarity	NPC91197
0.9341	High Similarity	NPC125551
0.9341	High Similarity	NPC155319
0.9341	High Similarity	NPC309503
0.9341	High Similarity	NPC239547
0.9341	High Similarity	NPC96597
0.8901	High Similarity	NPC67398
0.8901	High Similarity	NPC91654
0.8901	High Similarity	NPC474792
0.8889	High Similarity	NPC474249
0.8889	High Similarity	NPC261990
0.8842	High Similarity	NPC280991
0.8602	High Similarity	NPC211238
0.8587	High Similarity	NPC289361
0.8557	High Similarity	NPC470571
0.8526	High Similarity	NPC473555
0.8526	High Similarity	NPC471770
0.8526	High Similarity	NPC278939
0.8511	High Similarity	NPC286612
0.8511	High Similarity	NPC230347
0.8511	High Similarity	NPC275310
0.8438	Intermediate Similarity	NPC477928
0.8438	Intermediate Similarity	NPC157739
0.8404	Intermediate Similarity	NPC178949
0.8404	Intermediate Similarity	NPC96736
0.8387	Intermediate Similarity	NPC302584
0.8367	Intermediate Similarity	NPC154452
0.8351	Intermediate Similarity	NPC317019
0.8317	Intermediate Similarity	NPC392
0.8317	Intermediate Similarity	NPC177524
0.8317	Intermediate Similarity	NPC219900
0.83	Intermediate Similarity	NPC239961
0.83	Intermediate Similarity	NPC470767
0.83	Intermediate Similarity	NPC470763
0.8265	Intermediate Similarity	NPC21064
0.8265	Intermediate Similarity	NPC21568
0.8265	Intermediate Similarity	NPC198992
0.8265	Intermediate Similarity	NPC121072
0.8265	Intermediate Similarity	NPC285231
0.8261	Intermediate Similarity	NPC263079
0.8229	Intermediate Similarity	NPC90583
0.8211	Intermediate Similarity	NPC305160
0.8182	Intermediate Similarity	NPC121423
0.8173	Intermediate Similarity	NPC473125
0.8172	Intermediate Similarity	NPC309310
0.8172	Intermediate Similarity	NPC473058
0.8163	Intermediate Similarity	NPC477721
0.8163	Intermediate Similarity	NPC477716
0.8144	Intermediate Similarity	NPC240372
0.8132	Intermediate Similarity	NPC34581
0.8119	Intermediate Similarity	NPC473199
0.8119	Intermediate Similarity	NPC82251
0.8095	Intermediate Similarity	NPC44298
0.8095	Intermediate Similarity	NPC473159
0.8095	Intermediate Similarity	NPC473128
0.8095	Intermediate Similarity	NPC290608
0.8095	Intermediate Similarity	NPC40133
0.8095	Intermediate Similarity	NPC49413
0.8085	Intermediate Similarity	NPC159876
0.8085	Intermediate Similarity	NPC202886
0.8085	Intermediate Similarity	NPC471370
0.8085	Intermediate Similarity	NPC471371
0.8081	Intermediate Similarity	NPC477717
0.8081	Intermediate Similarity	NPC154127
0.8058	Intermediate Similarity	NPC206618
0.8043	Intermediate Similarity	NPC471369
0.8039	Intermediate Similarity	NPC472390
0.8039	Intermediate Similarity	NPC33053
0.8022	Intermediate Similarity	NPC166279
0.8021	Intermediate Similarity	NPC72817
0.8021	Intermediate Similarity	NPC477927
0.802	Intermediate Similarity	NPC31430
0.802	Intermediate Similarity	NPC470768
0.802	Intermediate Similarity	NPC85593
0.802	Intermediate Similarity	NPC173583
0.8019	Intermediate Similarity	NPC471633
0.8019	Intermediate Similarity	NPC69576
0.8019	Intermediate Similarity	NPC84949
0.8019	Intermediate Similarity	NPC31354
0.8	Intermediate Similarity	NPC177701
0.8	Intermediate Similarity	NPC94919
0.8	Intermediate Similarity	NPC48463
0.7981	Intermediate Similarity	NPC83005
0.7979	Intermediate Similarity	NPC477748
0.7961	Intermediate Similarity	NPC128795
0.7961	Intermediate Similarity	NPC38217
0.7961	Intermediate Similarity	NPC217921
0.7961	Intermediate Similarity	NPC38948
0.7961	Intermediate Similarity	NPC135015
0.7961	Intermediate Similarity	NPC48548
0.7961	Intermediate Similarity	NPC472988
0.7959	Intermediate Similarity	NPC477719
0.7959	Intermediate Similarity	NPC98112
0.7959	Intermediate Similarity	NPC97867
0.7959	Intermediate Similarity	NPC477718
0.7944	Intermediate Similarity	NPC199428
0.7944	Intermediate Similarity	NPC5311
0.7944	Intermediate Similarity	NPC193382
0.7944	Intermediate Similarity	NPC99620
0.7944	Intermediate Similarity	NPC310341
0.7941	Intermediate Similarity	NPC165405
0.7935	Intermediate Similarity	NPC164424
0.7925	Intermediate Similarity	NPC75167
0.7925	Intermediate Similarity	NPC264153
0.7925	Intermediate Similarity	NPC311592
0.7921	Intermediate Similarity	NPC473124
0.7921	Intermediate Similarity	NPC281378
0.7921	Intermediate Similarity	NPC473123
0.79	Intermediate Similarity	NPC11974
0.7885	Intermediate Similarity	NPC43976
0.7885	Intermediate Similarity	NPC296761
0.7885	Intermediate Similarity	NPC125361
0.7885	Intermediate Similarity	NPC40728
0.7885	Intermediate Similarity	NPC51925
0.7885	Intermediate Similarity	NPC154085
0.7885	Intermediate Similarity	NPC473570
0.7885	Intermediate Similarity	NPC316974
0.7879	Intermediate Similarity	NPC469725
0.7879	Intermediate Similarity	NPC158088
0.7879	Intermediate Similarity	NPC312325
0.7872	Intermediate Similarity	NPC248312
0.787	Intermediate Similarity	NPC99728
0.787	Intermediate Similarity	NPC473852
0.787	Intermediate Similarity	NPC203862
0.787	Intermediate Similarity	NPC471355
0.787	Intermediate Similarity	NPC158344
0.787	Intermediate Similarity	NPC93883
0.787	Intermediate Similarity	NPC27507
0.787	Intermediate Similarity	NPC471353
0.787	Intermediate Similarity	NPC34390
0.787	Intermediate Similarity	NPC474418
0.787	Intermediate Similarity	NPC77319
0.787	Intermediate Similarity	NPC87250
0.787	Intermediate Similarity	NPC196429
0.787	Intermediate Similarity	NPC142066
0.787	Intermediate Similarity	NPC243196
0.787	Intermediate Similarity	NPC50305
0.787	Intermediate Similarity	NPC471351
0.787	Intermediate Similarity	NPC290693
0.787	Intermediate Similarity	NPC309034
0.787	Intermediate Similarity	NPC244402
0.787	Intermediate Similarity	NPC152615
0.787	Intermediate Similarity	NPC157376
0.787	Intermediate Similarity	NPC471354
0.787	Intermediate Similarity	NPC84987
0.7864	Intermediate Similarity	NPC88013
0.7864	Intermediate Similarity	NPC234160
0.7864	Intermediate Similarity	NPC470169
0.7864	Intermediate Similarity	NPC470170
0.7864	Intermediate Similarity	NPC125423
0.7857	Intermediate Similarity	NPC472989
0.7857	Intermediate Similarity	NPC207617
0.785	Intermediate Similarity	NPC181145
0.7849	Intermediate Similarity	NPC471411
0.7849	Intermediate Similarity	NPC471368
0.7849	Intermediate Similarity	NPC471410
0.7843	Intermediate Similarity	NPC473127
0.7843	Intermediate Similarity	NPC470059
0.7843	Intermediate Similarity	NPC470057
0.7843	Intermediate Similarity	NPC470061
0.7843	Intermediate Similarity	NPC470062
0.7843	Intermediate Similarity	NPC470064
0.7843	Intermediate Similarity	NPC110656
0.7843	Intermediate Similarity	NPC470043
0.7843	Intermediate Similarity	NPC203354
0.7843	Intermediate Similarity	NPC93352
0.7843	Intermediate Similarity	NPC470058
0.7843	Intermediate Similarity	NPC470060
0.7835	Intermediate Similarity	NPC477722
0.7826	Intermediate Similarity	NPC471367
0.7822	Intermediate Similarity	NPC472815
0.7822	Intermediate Similarity	NPC238397
0.7822	Intermediate Similarity	NPC201191
0.7822	Intermediate Similarity	NPC471363
0.7818	Intermediate Similarity	NPC135369
0.7812	Intermediate Similarity	NPC477749
0.781	Intermediate Similarity	NPC177047
0.781	Intermediate Similarity	NPC103627
0.781	Intermediate Similarity	NPC191439
0.781	Intermediate Similarity	NPC170974
0.7802	Intermediate Similarity	NPC103171
0.78	Intermediate Similarity	NPC477968
0.78	Intermediate Similarity	NPC469942
0.78	Intermediate Similarity	NPC130792
0.78	Intermediate Similarity	NPC219285
0.78	Intermediate Similarity	NPC20113
0.78	Intermediate Similarity	NPC228251
0.78	Intermediate Similarity	NPC324841
0.78	Intermediate Similarity	NPC477972
0.78	Intermediate Similarity	NPC161527
0.78	Intermediate Similarity	NPC477971
0.7798	Intermediate Similarity	NPC83287
0.7789	Intermediate Similarity	NPC59682
0.7788	Intermediate Similarity	NPC295389
0.7788	Intermediate Similarity	NPC311223
0.7788	Intermediate Similarity	NPC80210
0.7788	Intermediate Similarity	NPC38376
0.7788	Intermediate Similarity	NPC295980
0.7788	Intermediate Similarity	NPC224414
0.7788	Intermediate Similarity	NPC230888

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 NPC474835 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	197
0.1-0.2	1941
0.2-0.3	3920
0.3-0.4	2043
0.4-0.5	616
0.5-0.6	330
0.6-0.7	81
0.7-0.8	21
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
0.8317	Intermediate Similarity	NPD6686	Approved
0.7925	Intermediate Similarity	NPD8133	Approved
0.7798	Intermediate Similarity	NPD7327	Approved
0.7798	Intermediate Similarity	NPD7328	Approved
0.7748	Intermediate Similarity	NPD7503	Approved
0.7727	Intermediate Similarity	NPD7516	Approved
0.7658	Intermediate Similarity	NPD8294	Approved
0.7658	Intermediate Similarity	NPD8377	Approved
0.7589	Intermediate Similarity	NPD8378	Approved
0.7589	Intermediate Similarity	NPD8033	Approved
0.7589	Intermediate Similarity	NPD8296	Approved
0.7589	Intermediate Similarity	NPD8380	Approved
0.7589	Intermediate Similarity	NPD8379	Approved
0.7589	Intermediate Similarity	NPD8335	Approved
0.7524	Intermediate Similarity	NPD6412	Phase 2
0.7453	Intermediate Similarity	NPD5345	Clinical (unspecified phase)
0.7328	Intermediate Similarity	NPD7507	Approved
0.7222	Intermediate Similarity	NPD8132	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD7319	Approved
0.7048	Intermediate Similarity	NPD5344	Discontinued
0.7019	Intermediate Similarity	NPD7638	Approved
0.7019	Intermediate Similarity	NPD8029	Clinical (unspecified phase)
0.6952	Remote Similarity	NPD7639	Approved
0.6952	Remote Similarity	NPD7640	Approved
0.6937	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6869	Remote Similarity	NPD7524	Approved
0.6864	Remote Similarity	NPD8328	Phase 3
0.6857	Remote Similarity	NPD4225	Approved
0.6832	Remote Similarity	NPD46	Approved
0.6832	Remote Similarity	NPD7838	Discovery
0.6832	Remote Similarity	NPD6698	Approved
0.6783	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6757	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6735	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6735	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6695	Remote Similarity	NPD8515	Approved
0.6695	Remote Similarity	NPD8516	Approved
0.6695	Remote Similarity	NPD8517	Approved
0.6695	Remote Similarity	NPD6921	Approved
0.6695	Remote Similarity	NPD8513	Phase 3
0.6639	Remote Similarity	NPD6370	Approved
0.6639	Remote Similarity	NPD7736	Approved
0.6636	Remote Similarity	NPD6648	Approved
0.6633	Remote Similarity	NPD6695	Phase 3
0.6633	Remote Similarity	NPD3670	Clinical (unspecified phase)
0.6633	Remote Similarity	NPD3669	Approved
0.6602	Remote Similarity	NPD7637	Suspended
0.6569	Remote Similarity	NPD6051	Approved
0.6559	Remote Similarity	NPD1810	Approved
0.6559	Remote Similarity	NPD1811	Approved
0.6557	Remote Similarity	NPD8293	Discontinued
0.6538	Remote Similarity	NPD8171	Discontinued
0.6529	Remote Similarity	NPD7492	Approved
0.6496	Remote Similarity	NPD6009	Approved
0.6496	Remote Similarity	NPD7115	Discovery
0.6475	Remote Similarity	NPD6616	Approved
0.6471	Remote Similarity	NPD6054	Approved
0.6442	Remote Similarity	NPD6411	Approved
0.6435	Remote Similarity	NPD6882	Approved
0.6423	Remote Similarity	NPD7078	Approved
0.6404	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6381	Remote Similarity	NPD6399	Phase 3
0.6379	Remote Similarity	NPD4632	Approved
0.6373	Remote Similarity	NPD7750	Discontinued
0.6364	Remote Similarity	NPD7632	Discontinued
0.6333	Remote Similarity	NPD6319	Approved
0.6333	Remote Similarity	NPD6059	Approved
0.6327	Remote Similarity	NPD7525	Registered
0.6327	Remote Similarity	NPD6930	Phase 2
0.6327	Remote Similarity	NPD6931	Approved
0.6296	Remote Similarity	NPD6083	Phase 2
0.6296	Remote Similarity	NPD6084	Phase 2
0.6293	Remote Similarity	NPD8297	Approved
0.6286	Remote Similarity	NPD8035	Phase 2
0.6286	Remote Similarity	NPD8034	Phase 2
0.6286	Remote Similarity	NPD7983	Approved
0.6281	Remote Similarity	NPD6016	Approved
0.6281	Remote Similarity	NPD6015	Approved
0.6261	Remote Similarity	NPD6371	Approved
0.625	Remote Similarity	NPD8170	Clinical (unspecified phase)
0.625	Remote Similarity	NPD6101	Approved
0.625	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.625	Remote Similarity	NPD6933	Approved
0.6237	Remote Similarity	NPD2686	Approved
0.6237	Remote Similarity	NPD2687	Approved
0.6237	Remote Similarity	NPD7532	Clinical (unspecified phase)
0.6237	Remote Similarity	NPD2254	Approved
0.623	Remote Similarity	NPD5988	Approved
0.6228	Remote Similarity	NPD6899	Approved
0.6228	Remote Similarity	NPD6881	Approved
0.6226	Remote Similarity	NPD5779	Approved
0.6226	Remote Similarity	NPD5778	Approved
0.6224	Remote Similarity	NPD6929	Approved
0.6224	Remote Similarity	NPD7645	Phase 2
0.621	Remote Similarity	NPD8451	Approved
0.62	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6195	Remote Similarity	NPD6675	Approved
0.6195	Remote Similarity	NPD7128	Approved
0.6195	Remote Similarity	NPD5739	Approved
0.6195	Remote Similarity	NPD6402	Approved
0.6186	Remote Similarity	NPD6932	Approved
0.6179	Remote Similarity	NPD6067	Discontinued
0.6176	Remote Similarity	NPD7625	Phase 1
0.6176	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6168	Remote Similarity	NPD7748	Approved
0.6162	Remote Similarity	NPD7514	Phase 3
0.6162	Remote Similarity	NPD7332	Phase 2
0.6162	Remote Similarity	NPD6928	Phase 2
0.616	Remote Similarity	NPD8448	Approved
0.616	Remote Similarity	NPD8074	Phase 3
0.6154	Remote Similarity	NPD6053	Discontinued
0.6147	Remote Similarity	NPD7902	Approved
0.6142	Remote Similarity	NPD8390	Approved
0.6142	Remote Similarity	NPD8391	Approved
0.6142	Remote Similarity	NPD8392	Approved
0.614	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.614	Remote Similarity	NPD5697	Approved
0.6132	Remote Similarity	NPD7087	Discontinued
0.6132	Remote Similarity	NPD7515	Phase 2
0.6122	Remote Similarity	NPD7145	Approved
0.6121	Remote Similarity	NPD6883	Approved
0.6121	Remote Similarity	NPD7102	Approved
0.6121	Remote Similarity	NPD7290	Approved
0.61	Remote Similarity	NPD1779	Approved
0.61	Remote Similarity	NPD1780	Approved
0.6098	Remote Similarity	NPD5125	Phase 3
0.6098	Remote Similarity	NPD5126	Approved
0.6087	Remote Similarity	NPD7320	Approved
0.6068	Remote Similarity	NPD6650	Approved
0.6068	Remote Similarity	NPD8130	Phase 1
0.6068	Remote Similarity	NPD6649	Approved
0.6068	Remote Similarity	NPD6847	Approved
0.6068	Remote Similarity	NPD6617	Approved
0.6068	Remote Similarity	NPD6869	Approved
0.6048	Remote Similarity	NPD7830	Approved
0.6048	Remote Similarity	NPD7604	Phase 2
0.6048	Remote Similarity	NPD7829	Approved
0.6042	Remote Similarity	NPD6924	Approved
0.6042	Remote Similarity	NPD6926	Approved
0.6038	Remote Similarity	NPD3168	Discontinued
0.6034	Remote Similarity	NPD6012	Approved
0.6034	Remote Similarity	NPD6014	Approved
0.6034	Remote Similarity	NPD6372	Approved
0.6034	Remote Similarity	NPD6013	Approved
0.6034	Remote Similarity	NPD6373	Approved
0.602	Remote Similarity	NPD6925	Approved
0.602	Remote Similarity	NPD5776	Phase 2
0.6019	Remote Similarity	NPD6893	Approved
0.6016	Remote Similarity	NPD8444	Approved
0.6016	Remote Similarity	NPD5983	Phase 2
0.6	Remote Similarity	NPD8340	Approved
0.6	Remote Similarity	NPD8341	Approved
0.6	Remote Similarity	NPD8342	Approved
0.6	Remote Similarity	NPD8299	Approved
0.6	Remote Similarity	NPD5701	Approved
0.6	Remote Similarity	NPD6940	Discontinued
0.6	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.5979	Remote Similarity	NPD6942	Approved
0.5979	Remote Similarity	NPD7339	Approved
0.5963	Remote Similarity	NPD5695	Phase 3
0.5962	Remote Similarity	NPD7334	Approved
0.5962	Remote Similarity	NPD7521	Approved
0.5962	Remote Similarity	NPD6684	Approved
0.5962	Remote Similarity	NPD7146	Approved
0.5962	Remote Similarity	NPD6409	Approved
0.5962	Remote Similarity	NPD5330	Approved
0.5952	Remote Similarity	NPD6336	Discontinued
0.5948	Remote Similarity	NPD6011	Approved
0.5946	Remote Similarity	NPD5696	Approved
0.5941	Remote Similarity	NPD6898	Phase 1
0.5941	Remote Similarity	NPD6902	Approved
0.5923	Remote Similarity	NPD8449	Approved
0.5922	Remote Similarity	NPD4786	Approved
0.592	Remote Similarity	NPD7642	Approved
0.5918	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.5913	Remote Similarity	NPD6640	Phase 3
0.5909	Remote Similarity	NPD4792	Clinical (unspecified phase)
0.5909	Remote Similarity	NPD7839	Suspended
0.5905	Remote Similarity	NPD4751	Clinical (unspecified phase)
0.5905	Remote Similarity	NPD4251	Approved
0.5905	Remote Similarity	NPD4250	Approved
0.5902	Remote Similarity	NPD7641	Discontinued
0.59	Remote Similarity	NPD6683	Phase 2
0.5891	Remote Similarity	NPD5956	Approved
0.5882	Remote Similarity	NPD3667	Approved
0.5878	Remote Similarity	NPD8450	Suspended
0.5872	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.5872	Remote Similarity	NPD7900	Approved
0.5872	Remote Similarity	NPD5282	Discontinued
0.5865	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.5865	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.5859	Remote Similarity	NPD6033	Approved
0.5849	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.5849	Remote Similarity	NPD6903	Approved
0.5849	Remote Similarity	NPD5737	Approved
0.5849	Remote Similarity	NPD6672	Approved
0.5847	Remote Similarity	NPD4634	Approved
0.5842	Remote Similarity	NPD4820	Approved
0.5842	Remote Similarity	NPD4819	Approved
0.5842	Remote Similarity	NPD4821	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