NPASS Compound

Structure

NPC470571 OpenBabel07101718332D 34 36 0 0 1 0 0 0 0 0999 V2000 0.8660 -3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9641 -6.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4641 -6.0000 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 2.5981 -4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 1.0000 0.0000 C 0 0 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 0.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -5.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.7321 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -2.0000 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 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 -1.7321 1.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0000 1.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.4641 -6.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.5981 2.5000 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 2.5981 -6.5000 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 2.5000 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 16 1 0 0 0 0 2 17 1 0 0 0 0 3 18 1 0 0 0 0 4 26 1 0 0 0 0 5 26 1 0 0 0 0 7 8 1 0 0 0 0 7 13 2 0 0 0 0 8 16 2 0 0 0 0 9 12 1 0 0 0 0 9 17 1 0 0 0 0 10 11 1 0 0 0 0 10 19 1 0 0 0 0 11 20 1 0 0 0 0 12 22 1 0 0 0 0 13 26 1 0 0 0 0 14 19 1 0 0 0 0 14 27 1 0 0 0 0 15 21 1 0 0 0 0 15 32 1 0 0 0 0 17 27 1 6 0 0 0 18 28 2 0 0 0 0 18 33 1 0 0 0 0 19 16 1 1 0 0 0 20 22 1 0 0 0 0 20 27 1 6 0 0 0 21 23 1 0 0 0 0 21 29 1 1 0 0 0 22 34 1 1 0 0 0 23 24 1 0 0 0 0 23 30 1 1 0 0 0 24 25 1 0 0 0 0 24 33 1 6 0 0 0 25 32 1 0 0 0 0 25 34 1 1 0 0 0 26 31 1 0 0 0 0 27 6 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	480.31
Volume:	503.501
LogP:	3.09
LogD:	3.253
LogS:	-4.088
# Rotatable Bonds:	7
TPSA:	105.45
# H-Bond Aceptor:	7
# H-Bond Donor:	3
# Rings:	3
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.395
Synthetic Accessibility Score:	5.01
Fsp3:	0.815
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:	-4.707
MDCK Permeability:	6.599578046007082e-05
Pgp-inhibitor:	0.991
Pgp-substrate:	0.997
Human Intestinal Absorption (HIA):	0.026
20% Bioavailability (F20%):	0.009
30% Bioavailability (F30%):	0.203

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.061
Plasma Protein Binding (PPB):	61.73414611816406%
Volume Distribution (VD):	0.811
Pgp-substrate:	17.47148323059082%

ADMET: Metabolism

CYP1A2-inhibitor:	0.018
CYP1A2-substrate:	0.097
CYP2C19-inhibitor:	0.022
CYP2C19-substrate:	0.699
CYP2C9-inhibitor:	0.023
CYP2C9-substrate:	0.335
CYP2D6-inhibitor:	0.026
CYP2D6-substrate:	0.655
CYP3A4-inhibitor:	0.555
CYP3A4-substrate:	0.319

ADMET: Excretion

Clearance (CL):	2.302
Half-life (T1/2):	0.235

ADMET: Toxicity

hERG Blockers:	0.881
Human Hepatotoxicity (H-HT):	0.667
Drug-inuced Liver Injury (DILI):	0.685
AMES Toxicity:	0.282
Rat Oral Acute Toxicity:	0.028
Maximum Recommended Daily Dose:	0.133
Skin Sensitization:	0.946
Carcinogencity:	0.296
Eye Corrosion:	0.013
Eye Irritation:	0.045
Respiratory Toxicity:	0.976

Download Data

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

Natural Product: NPC470571

Natural Product ID:	NPC470571
*Common Name:**	(-)-Fuscoside A
IUPAC Name:	[(2R,3S,4R,5R)-2-[[(1S,4S,4aR,6S,8aS)-6-[(2E,4E)-6-hydroxy-6-methylhepta-2,4-dien-2-yl]-4,4a-dimethyl-2,3,4,5,6,7,8,8a-octahydro-1H-naphthalen-1-yl]oxy]-4,5-dihydroxyoxan-3-yl] acetate
Synonyms:	(-)-Fuscoside A
Standard InCHIKey:	MRYOFKDORPTZIE-BIEVFPKMSA-N
Standard InCHI:	InChI=1S/C27H44O7/c1-16(8-7-13-26(4,5)31)19-10-11-20-22(12-9-17(2)27(20,6)14-19)34-25-24(33-18(3)28)23(30)21(29)15-32-25/h7-8,13,17,19-25,29-31H,9-12,14-15H2,1-6H3/b13-7+,16-8+/t17-,19-,20+,21+,22-,23+,24-,25+,27+/m0/s1
SMILES:	CC1CCC(C2C1(CC(CC2)C(=CC=CC(C)(C)O)C)C)OC3C(C(C(CO3)O)O)OC(=O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2071305
PubChem CID:	70688906
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001550] Sesquiterpenoids [CHEMONTID:0003655] Eremophilane, 8,9-secoeremophilane and furoeremophilane sesquiterpenoids

*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
NPO27691	Eunicea fusca	Species	Plexauridae	Eukaryota	n.a.	Caribbean	n.a.	PMID[21865038]
NPO27691	Eunicea fusca	Species	Plexauridae	Eukaryota	n.a.	n.a.	n.a.	PMID[22734800]
NPO27691	Eunicea fusca	Species	Plexauridae	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	1

Activity Type	# Activity
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT32	Organism	Mus musculus	Mus musculus	Inhibition	=	85.0	%	PMID[491456]

☑ 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 NPC470571 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	218
0.1-0.2	1280
0.2-0.3	4152
0.3-0.4	8688
0.4-0.5	13164
0.5-0.6	7224
0.6-0.7	5354
0.7-0.8	2455
0.8-0.85	134
0.85-0.9	22
0.9-0.95	5
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9255	High Similarity	NPC211238
0.9062	High Similarity	NPC90583
0.8911	High Similarity	NPC470763
0.8911	High Similarity	NPC470767
0.8854	High Similarity	NPC178949
0.8854	High Similarity	NPC96736
0.8812	High Similarity	NPC470768
0.8776	High Similarity	NPC239547
0.8776	High Similarity	NPC91197
0.8776	High Similarity	NPC240372
0.8776	High Similarity	NPC309503
0.8776	High Similarity	NPC155319
0.8776	High Similarity	NPC96597
0.8776	High Similarity	NPC125551
0.87	High Similarity	NPC280991
0.8687	High Similarity	NPC477928
0.866	High Similarity	NPC305160
0.8646	High Similarity	NPC302584
0.8571	High Similarity	NPC286612
0.8571	High Similarity	NPC230347
0.8571	High Similarity	NPC275310
0.8557	High Similarity	NPC474835
0.8544	High Similarity	NPC473199
0.8515	High Similarity	NPC121072
0.8515	High Similarity	NPC21064
0.8476	Intermediate Similarity	NPC206618
0.8476	Intermediate Similarity	NPC316974
0.8462	Intermediate Similarity	NPC472390
0.8447	Intermediate Similarity	NPC85593
0.8447	Intermediate Similarity	NPC173583
0.8447	Intermediate Similarity	NPC31430
0.8438	Intermediate Similarity	NPC16265
0.8438	Intermediate Similarity	NPC309310
0.8431	Intermediate Similarity	NPC154452
0.8426	Intermediate Similarity	NPC220293
0.8416	Intermediate Similarity	NPC64348
0.8411	Intermediate Similarity	NPC470025
0.8411	Intermediate Similarity	NPC328074
0.8411	Intermediate Similarity	NPC473125
0.8411	Intermediate Similarity	NPC317460
0.8411	Intermediate Similarity	NPC321272
0.8396	Intermediate Similarity	NPC177047
0.8381	Intermediate Similarity	NPC311223
0.8381	Intermediate Similarity	NPC472988
0.8381	Intermediate Similarity	NPC38948
0.8381	Intermediate Similarity	NPC38217
0.8381	Intermediate Similarity	NPC48548
0.8381	Intermediate Similarity	NPC128795
0.8381	Intermediate Similarity	NPC135015
0.8381	Intermediate Similarity	NPC217921
0.8367	Intermediate Similarity	NPC91654
0.8367	Intermediate Similarity	NPC67398
0.8367	Intermediate Similarity	NPC474792
0.8365	Intermediate Similarity	NPC470056
0.8365	Intermediate Similarity	NPC472900
0.8365	Intermediate Similarity	NPC218158
0.8365	Intermediate Similarity	NPC472898
0.8365	Intermediate Similarity	NPC470055
0.8365	Intermediate Similarity	NPC82251
0.8365	Intermediate Similarity	NPC472899
0.8364	Intermediate Similarity	NPC473617
0.8364	Intermediate Similarity	NPC473828
0.8351	Intermediate Similarity	NPC474249
0.8351	Intermediate Similarity	NPC261990
0.835	Intermediate Similarity	NPC162354
0.835	Intermediate Similarity	NPC473129
0.835	Intermediate Similarity	NPC134270
0.835	Intermediate Similarity	NPC99627
0.8349	Intermediate Similarity	NPC146652
0.8333	Intermediate Similarity	NPC473159
0.8333	Intermediate Similarity	NPC470027
0.8333	Intermediate Similarity	NPC44298
0.8333	Intermediate Similarity	NPC40133
0.8333	Intermediate Similarity	NPC473128
0.8333	Intermediate Similarity	NPC290608
0.8333	Intermediate Similarity	NPC49413
0.8318	Intermediate Similarity	NPC17791
0.8318	Intermediate Similarity	NPC208189
0.8318	Intermediate Similarity	NPC65034
0.8302	Intermediate Similarity	NPC43976
0.8302	Intermediate Similarity	NPC154085
0.8302	Intermediate Similarity	NPC40728
0.8302	Intermediate Similarity	NPC296761
0.8302	Intermediate Similarity	NPC125361
0.8302	Intermediate Similarity	NPC51925
0.8288	Intermediate Similarity	NPC268326
0.8288	Intermediate Similarity	NPC153085
0.8286	Intermediate Similarity	NPC88013
0.8286	Intermediate Similarity	NPC125423
0.8286	Intermediate Similarity	NPC283849
0.8286	Intermediate Similarity	NPC231340
0.8286	Intermediate Similarity	NPC234160
0.8283	Intermediate Similarity	NPC72817
0.8283	Intermediate Similarity	NPC477927
0.8269	Intermediate Similarity	NPC470060
0.8269	Intermediate Similarity	NPC470321
0.8269	Intermediate Similarity	NPC264867
0.8269	Intermediate Similarity	NPC57065
0.8269	Intermediate Similarity	NPC470043
0.8269	Intermediate Similarity	NPC81567
0.8269	Intermediate Similarity	NPC109792
0.8269	Intermediate Similarity	NPC470062
0.8269	Intermediate Similarity	NPC75608
0.8269	Intermediate Similarity	NPC54521
0.8269	Intermediate Similarity	NPC470064
0.8269	Intermediate Similarity	NPC470061
0.8269	Intermediate Similarity	NPC470057
0.8269	Intermediate Similarity	NPC473207
0.8269	Intermediate Similarity	NPC470059
0.8269	Intermediate Similarity	NPC201880
0.8269	Intermediate Similarity	NPC470058
0.8265	Intermediate Similarity	NPC289361
0.8257	Intermediate Similarity	NPC471633
0.8257	Intermediate Similarity	NPC475163
0.8257	Intermediate Similarity	NPC472274
0.8257	Intermediate Similarity	NPC84949
0.8257	Intermediate Similarity	NPC31354
0.8257	Intermediate Similarity	NPC69576
0.8252	Intermediate Similarity	NPC471363
0.8252	Intermediate Similarity	NPC150463
0.8252	Intermediate Similarity	NPC214277
0.8252	Intermediate Similarity	NPC121423
0.8252	Intermediate Similarity	NPC472815
0.8252	Intermediate Similarity	NPC238397
0.8247	Intermediate Similarity	NPC473058
0.8241	Intermediate Similarity	NPC174836
0.8241	Intermediate Similarity	NPC231797
0.8235	Intermediate Similarity	NPC317019
0.8235	Intermediate Similarity	NPC324841
0.8224	Intermediate Similarity	NPC316708
0.8224	Intermediate Similarity	NPC119550
0.8218	Intermediate Similarity	NPC471770
0.8218	Intermediate Similarity	NPC278939
0.8218	Intermediate Similarity	NPC98112
0.8218	Intermediate Similarity	NPC473555
0.8208	Intermediate Similarity	NPC177246
0.8208	Intermediate Similarity	NPC470024
0.8208	Intermediate Similarity	NPC476123
0.8208	Intermediate Similarity	NPC472896
0.8208	Intermediate Similarity	NPC284807
0.8208	Intermediate Similarity	NPC28198
0.8208	Intermediate Similarity	NPC472897
0.819	Intermediate Similarity	NPC252296
0.819	Intermediate Similarity	NPC239961
0.8182	Intermediate Similarity	NPC199428
0.8182	Intermediate Similarity	NPC5311
0.8182	Intermediate Similarity	NPC310341
0.8182	Intermediate Similarity	NPC193382
0.8182	Intermediate Similarity	NPC99620
0.8173	Intermediate Similarity	NPC127933
0.8173	Intermediate Similarity	NPC473124
0.8173	Intermediate Similarity	NPC475889
0.8173	Intermediate Similarity	NPC473123
0.8173	Intermediate Similarity	NPC7644
0.8173	Intermediate Similarity	NPC473198
0.8173	Intermediate Similarity	NPC7613
0.8173	Intermediate Similarity	NPC45897
0.8173	Intermediate Similarity	NPC281378
0.8165	Intermediate Similarity	NPC264153
0.8163	Intermediate Similarity	NPC159876
0.8163	Intermediate Similarity	NPC469403
0.8158	Intermediate Similarity	NPC41129
0.8155	Intermediate Similarity	NPC309425
0.8155	Intermediate Similarity	NPC160734
0.8155	Intermediate Similarity	NPC11974
0.8155	Intermediate Similarity	NPC47566
0.8155	Intermediate Similarity	NPC267510
0.8155	Intermediate Similarity	NPC235920
0.8155	Intermediate Similarity	NPC198992
0.8155	Intermediate Similarity	NPC96784
0.8155	Intermediate Similarity	NPC470434
0.8155	Intermediate Similarity	NPC88000
0.8155	Intermediate Similarity	NPC129372
0.8155	Intermediate Similarity	NPC470054
0.8155	Intermediate Similarity	NPC4831
0.8155	Intermediate Similarity	NPC472023
0.8148	Intermediate Similarity	NPC190837
0.8148	Intermediate Similarity	NPC470026
0.8148	Intermediate Similarity	NPC65167
0.8148	Intermediate Similarity	NPC292196
0.8144	Intermediate Similarity	NPC263079
0.8142	Intermediate Similarity	NPC233500
0.8137	Intermediate Similarity	NPC5358
0.8137	Intermediate Similarity	NPC234287
0.8137	Intermediate Similarity	NPC476895
0.8137	Intermediate Similarity	NPC280825
0.8137	Intermediate Similarity	NPC216260
0.8137	Intermediate Similarity	NPC157739
0.8131	Intermediate Similarity	NPC167383
0.8131	Intermediate Similarity	NPC306746
0.8131	Intermediate Similarity	NPC237503
0.8131	Intermediate Similarity	NPC137917
0.8131	Intermediate Similarity	NPC127853
0.8131	Intermediate Similarity	NPC57362
0.8131	Intermediate Similarity	NPC204407
0.8125	Intermediate Similarity	NPC219656
0.8119	Intermediate Similarity	NPC207617
0.8113	Intermediate Similarity	NPC293512
0.8113	Intermediate Similarity	NPC122816
0.8113	Intermediate Similarity	NPC473538

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 NPC470571 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	190
0.1-0.2	1414
0.2-0.3	3723
0.3-0.4	2400
0.4-0.5	930
0.5-0.6	307
0.6-0.7	159
0.7-0.8	27
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8142	Intermediate Similarity	NPD7503	Approved
0.8036	Intermediate Similarity	NPD7328	Approved
0.8036	Intermediate Similarity	NPD7327	Approved
0.7965	Intermediate Similarity	NPD7516	Approved
0.7895	Intermediate Similarity	NPD8377	Approved
0.7895	Intermediate Similarity	NPD8294	Approved
0.787	Intermediate Similarity	NPD6686	Approved
0.7826	Intermediate Similarity	NPD8033	Approved
0.7826	Intermediate Similarity	NPD8296	Approved
0.7826	Intermediate Similarity	NPD8380	Approved
0.7826	Intermediate Similarity	NPD8378	Approved
0.7826	Intermediate Similarity	NPD8335	Approved
0.7826	Intermediate Similarity	NPD8379	Approved
0.7636	Intermediate Similarity	NPD8132	Clinical (unspecified phase)
0.7563	Intermediate Similarity	NPD7507	Approved
0.7455	Intermediate Similarity	NPD6412	Phase 2
0.7383	Intermediate Similarity	NPD7640	Approved
0.7383	Intermediate Similarity	NPD7639	Approved
0.7377	Intermediate Similarity	NPD7319	Approved
0.7373	Intermediate Similarity	NPD8513	Phase 3
0.7373	Intermediate Similarity	NPD8516	Approved
0.7373	Intermediate Similarity	NPD8517	Approved
0.7373	Intermediate Similarity	NPD8515	Approved
0.7368	Intermediate Similarity	NPD8133	Approved
0.7315	Intermediate Similarity	NPD5344	Discontinued
0.729	Intermediate Similarity	NPD7638	Approved
0.729	Intermediate Similarity	NPD4225	Approved
0.725	Intermediate Similarity	NPD8328	Phase 3
0.7222	Intermediate Similarity	NPD6648	Approved
0.7179	Intermediate Similarity	NPD8295	Clinical (unspecified phase)
0.7157	Intermediate Similarity	NPD7524	Approved
0.713	Intermediate Similarity	NPD8029	Clinical (unspecified phase)
0.708	Intermediate Similarity	NPD5345	Clinical (unspecified phase)
0.7048	Intermediate Similarity	NPD7637	Suspended
0.7034	Intermediate Similarity	NPD7115	Discovery
0.703	Intermediate Similarity	NPD7338	Clinical (unspecified phase)
0.7025	Intermediate Similarity	NPD6370	Approved
0.7018	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.7016	Intermediate Similarity	NPD7736	Approved
0.6983	Remote Similarity	NPD6882	Approved
0.697	Remote Similarity	NPD7525	Registered
0.6935	Remote Similarity	NPD8293	Discontinued
0.6931	Remote Similarity	NPD6695	Phase 3
0.6911	Remote Similarity	NPD7492	Approved
0.6891	Remote Similarity	NPD6009	Approved
0.6887	Remote Similarity	NPD6411	Approved
0.6869	Remote Similarity	NPD7645	Phase 2
0.686	Remote Similarity	NPD6054	Approved
0.6855	Remote Similarity	NPD6616	Approved
0.6838	Remote Similarity	NPD8297	Approved
0.6822	Remote Similarity	NPD5779	Approved
0.6822	Remote Similarity	NPD5778	Approved
0.68	Remote Similarity	NPD7078	Approved
0.68	Remote Similarity	NPD8074	Phase 3
0.6792	Remote Similarity	NPD7838	Discovery
0.6786	Remote Similarity	NPD7632	Discontinued
0.6783	Remote Similarity	NPD6881	Approved
0.6783	Remote Similarity	NPD6899	Approved
0.678	Remote Similarity	NPD4632	Approved
0.6759	Remote Similarity	NPD7748	Approved
0.6754	Remote Similarity	NPD7128	Approved
0.6754	Remote Similarity	NPD5739	Approved
0.6754	Remote Similarity	NPD6675	Approved
0.6754	Remote Similarity	NPD6402	Approved
0.6752	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6729	Remote Similarity	NPD7983	Approved
0.6729	Remote Similarity	NPD7515	Phase 2
0.6727	Remote Similarity	NPD7902	Approved
0.6721	Remote Similarity	NPD6059	Approved
0.6721	Remote Similarity	NPD6319	Approved
0.6699	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6698	Remote Similarity	NPD6101	Approved
0.6698	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6696	Remote Similarity	NPD5697	Approved
0.6667	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD7102	Approved
0.6667	Remote Similarity	NPD6016	Approved
0.6667	Remote Similarity	NPD6883	Approved
0.6667	Remote Similarity	NPD6399	Phase 3
0.6667	Remote Similarity	NPD7290	Approved
0.6667	Remote Similarity	NPD7750	Discontinued
0.6667	Remote Similarity	NPD6015	Approved
0.6638	Remote Similarity	NPD7320	Approved
0.6634	Remote Similarity	NPD6930	Phase 2
0.6634	Remote Similarity	NPD7514	Phase 3
0.6634	Remote Similarity	NPD7332	Phase 2
0.6634	Remote Similarity	NPD6931	Approved
0.6633	Remote Similarity	NPD8264	Approved
0.6613	Remote Similarity	NPD5988	Approved
0.661	Remote Similarity	NPD6617	Approved
0.661	Remote Similarity	NPD6649	Approved
0.661	Remote Similarity	NPD8130	Phase 1
0.661	Remote Similarity	NPD6847	Approved
0.661	Remote Similarity	NPD6869	Approved
0.661	Remote Similarity	NPD6650	Approved
0.6581	Remote Similarity	NPD6013	Approved
0.6581	Remote Similarity	NPD6372	Approved
0.6581	Remote Similarity	NPD6373	Approved
0.6581	Remote Similarity	NPD6014	Approved
0.6581	Remote Similarity	NPD6012	Approved
0.6566	Remote Similarity	NPD6933	Approved
0.656	Remote Similarity	NPD6067	Discontinued
0.6552	Remote Similarity	NPD5701	Approved
0.6542	Remote Similarity	NPD6051	Approved
0.6535	Remote Similarity	NPD6929	Approved
0.6496	Remote Similarity	NPD6011	Approved
0.6491	Remote Similarity	NPD5211	Phase 2
0.6481	Remote Similarity	NPD6698	Approved
0.6481	Remote Similarity	NPD46	Approved
0.6455	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6455	Remote Similarity	NPD7900	Approved
0.6442	Remote Similarity	NPD3670	Clinical (unspecified phase)
0.6442	Remote Similarity	NPD3669	Approved
0.6436	Remote Similarity	NPD7145	Approved
0.6436	Remote Similarity	NPD7322	Clinical (unspecified phase)
0.6429	Remote Similarity	NPD7604	Phase 2
0.6429	Remote Similarity	NPD6083	Phase 2
0.6429	Remote Similarity	NPD6084	Phase 2
0.6422	Remote Similarity	NPD8035	Phase 2
0.6422	Remote Similarity	NPD7087	Discontinued
0.6422	Remote Similarity	NPD8034	Phase 2
0.641	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6408	Remote Similarity	NPD6902	Approved
0.6403	Remote Similarity	NPD7625	Phase 1
0.64	Remote Similarity	NPD6921	Approved
0.64	Remote Similarity	NPD5983	Phase 2
0.6379	Remote Similarity	NPD5141	Approved
0.6378	Remote Similarity	NPD8299	Approved
0.6378	Remote Similarity	NPD8340	Approved
0.6378	Remote Similarity	NPD8342	Approved
0.6378	Remote Similarity	NPD8341	Approved
0.6364	Remote Similarity	NPD1810	Approved
0.6364	Remote Similarity	NPD6924	Approved
0.6364	Remote Similarity	NPD8171	Discontinued
0.6364	Remote Similarity	NPD6926	Approved
0.6364	Remote Similarity	NPD1811	Approved
0.6355	Remote Similarity	NPD3573	Approved
0.6355	Remote Similarity	NPD4751	Clinical (unspecified phase)
0.6339	Remote Similarity	NPD7839	Suspended
0.6337	Remote Similarity	NPD6932	Approved
0.6337	Remote Similarity	NPD6925	Approved
0.6337	Remote Similarity	NPD5776	Phase 2
0.6333	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.633	Remote Similarity	NPD3168	Discontinued
0.6328	Remote Similarity	NPD6336	Discontinued
0.6321	Remote Similarity	NPD6893	Approved
0.6321	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6316	Remote Similarity	NPD5286	Approved
0.6316	Remote Similarity	NPD5285	Approved
0.6316	Remote Similarity	NPD4696	Approved
0.6311	Remote Similarity	NPD7509	Discontinued
0.63	Remote Similarity	NPD6942	Approved
0.63	Remote Similarity	NPD7339	Approved
0.6283	Remote Similarity	NPD4755	Approved
0.6273	Remote Similarity	NPD6079	Approved
0.6262	Remote Similarity	NPD3618	Phase 1
0.625	Remote Similarity	NPD4634	Approved
0.625	Remote Similarity	NPD6898	Phase 1
0.624	Remote Similarity	NPD7101	Approved
0.624	Remote Similarity	NPD7100	Approved
0.6239	Remote Similarity	NPD5328	Approved
0.6238	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.6231	Remote Similarity	NPD6033	Approved
0.6226	Remote Similarity	NPD4786	Approved
0.622	Remote Similarity	NPD5126	Approved
0.622	Remote Similarity	NPD5125	Phase 3
0.6216	Remote Similarity	NPD4202	Approved
0.6207	Remote Similarity	NPD5226	Approved
0.6207	Remote Similarity	NPD4633	Approved
0.6207	Remote Similarity	NPD5225	Approved
0.6207	Remote Similarity	NPD5224	Approved
0.6202	Remote Similarity	NPD8451	Approved
0.619	Remote Similarity	NPD3667	Approved
0.6186	Remote Similarity	NPD6008	Approved
0.6174	Remote Similarity	NPD4700	Approved
0.6162	Remote Similarity	NPD7150	Approved
0.6162	Remote Similarity	NPD7152	Approved
0.6162	Remote Similarity	NPD7151	Approved
0.616	Remote Similarity	NPD6335	Approved
0.6154	Remote Similarity	NPD8448	Approved
0.6154	Remote Similarity	NPD4822	Approved
0.6154	Remote Similarity	NPD5174	Approved
0.6154	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6154	Remote Similarity	NPD5175	Approved
0.6154	Remote Similarity	NPD4821	Approved
0.6154	Remote Similarity	NPD4820	Approved
0.6154	Remote Similarity	NPD4819	Approved
0.6136	Remote Similarity	NPD8390	Approved
0.6136	Remote Similarity	NPD8391	Approved
0.6136	Remote Similarity	NPD8392	Approved
0.6129	Remote Similarity	NPD6274	Approved
0.6126	Remote Similarity	NPD5281	Approved
0.6126	Remote Similarity	NPD5284	Approved
0.6121	Remote Similarity	NPD4159	Approved
0.6121	Remote Similarity	NPD5223	Approved
0.6116	Remote Similarity	NPD6371	Approved
0.6111	Remote Similarity	NPD5330	Approved
0.6111	Remote Similarity	NPD7334	Approved
0.6111	Remote Similarity	NPD6409	Approved
0.6111	Remote Similarity	NPD7146	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