NPASS Compound

Structure

NPC470057 OpenBabel07101718322D 41 45 0 0 1 0 0 0 0 0999 V2000 7.4527 -4.1522 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.4527 -1.1522 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.9527 -0.2862 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8138 3.1884 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2205 2.2749 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5348 -0.4612 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8546 -1.6522 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8546 1.3478 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9945 -1.8366 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5215 3.9617 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7861 1.9305 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7807 1.8259 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9886 -1.1522 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.5867 -2.6522 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1226 -0.6522 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.7206 -2.1522 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6581 1.4781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.5867 0.3478 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.3187 -3.6522 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4013 0.8090 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.3794 1.0169 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.2079 0.9781 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.9886 0.8478 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8546 -0.6522 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 6.5867 -0.6522 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 5.7206 0.8478 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 7.4527 -2.1522 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.1215 1.3849 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.9945 -0.1045 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 7.4527 -1.1522 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2260 2.3794 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1226 0.3478 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 5.7206 -1.1522 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 4.8546 0.3478 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 9.1847 -4.1522 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.7206 1.8478 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.9305 0.7971 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.4945 -0.9706 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.4170 2.9672 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 8.3187 -2.6522 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 19 1 0 0 0 0 2 30 1 0 0 0 0 3 30 1 0 0 0 0 4 31 1 0 0 0 0 5 31 1 0 0 0 0 9 38 1 0 0 0 0 10 39 1 0 0 0 0 11 12 1 0 0 0 0 11 21 1 0 0 0 0 12 23 2 0 0 0 0 13 15 1 0 0 0 0 13 24 1 0 0 0 0 14 16 1 0 0 0 0 14 27 1 0 0 0 0 15 32 1 0 0 0 0 16 33 1 0 0 0 0 17 22 1 0 0 0 0 18 25 1 0 0 0 0 18 26 1 0 0 0 0 19 35 2 0 0 0 0 19 40 1 0 0 0 0 20 17 1 1 0 0 0 20 21 1 0 0 0 0 20 29 1 0 0 0 0 21 32 1 1 0 0 0 22 28 1 1 0 0 0 22 41 1 0 0 0 0 23 32 1 0 0 0 0 23 34 1 0 0 0 0 24 33 1 1 0 0 0 24 34 1 0 0 0 0 25 30 1 0 0 0 0 25 33 1 1 0 0 0 26 34 1 6 0 0 0 26 36 1 0 0 0 0 27 30 1 0 0 0 0 27 40 1 6 0 0 0 28 31 1 0 0 0 0 28 37 1 6 0 0 0 29 38 1 6 0 0 0 29 41 1 0 0 0 0 31 39 1 0 0 0 0 32 6 1 6 0 0 0 33 7 1 1 0 0 0 34 8 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	576.4
Volume:	610.096
LogP:	4.626
LogD:	3.99
LogS:	-4.856
# Rotatable Bonds:	7
TPSA:	94.45
# H-Bond Aceptor:	7
# H-Bond Donor:	2
# Rings:	5
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.311
Synthetic Accessibility Score:	5.479
Fsp3:	0.912
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.957
MDCK Permeability:	1.7797092368709855e-05
Pgp-inhibitor:	0.999
Pgp-substrate:	0.003
Human Intestinal Absorption (HIA):	0.002
20% Bioavailability (F20%):	0.085
30% Bioavailability (F30%):	0.721

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.01
Plasma Protein Binding (PPB):	87.71126556396484%
Volume Distribution (VD):	1.825
Pgp-substrate:	9.548558235168457%

ADMET: Metabolism

CYP1A2-inhibitor:	0.002
CYP1A2-substrate:	0.155
CYP2C19-inhibitor:	0.009
CYP2C19-substrate:	0.855
CYP2C9-inhibitor:	0.05
CYP2C9-substrate:	0.045
CYP2D6-inhibitor:	0.005
CYP2D6-substrate:	0.09
CYP3A4-inhibitor:	0.347
CYP3A4-substrate:	0.516

ADMET: Excretion

Clearance (CL):	4.394
Half-life (T1/2):	0.212

ADMET: Toxicity

hERG Blockers:	0.145
Human Hepatotoxicity (H-HT):	0.334
Drug-inuced Liver Injury (DILI):	0.102
AMES Toxicity:	0.022
Rat Oral Acute Toxicity:	0.321
Maximum Recommended Daily Dose:	0.349
Skin Sensitization:	0.511
Carcinogencity:	0.008
Eye Corrosion:	0.004
Eye Irritation:	0.014
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: NPC470057

Natural Product ID:	NPC470057
*Common Name:**	Chisopanin E
IUPAC Name:	[(3R,5R,7R,8R,9R,10S,13S,17R)-7-hydroxy-17-[(2R,3S,5R)-5-[(1S)-1-hydroxy-2-methoxy-2-methylpropyl]-2-methoxyoxolan-3-yl]-4,4,8,10,13-pentamethyl-2,3,5,6,7,9,11,12,16,17-decahydro-1H-cyclopenta[a]phenanthren-3-yl] acetate
Synonyms:	Chisopanin E
Standard InCHIKey:	SABPQJQTNUXWFJ-QWWOOTIISA-N
Standard InCHI:	InChI=1S/C34H56O7/c1-19(35)40-27-14-16-33(7)24-13-15-32(6)21(20-17-22(41-29(20)38-9)28(37)31(4,5)39-10)11-12-23(32)34(24,8)26(36)18-25(33)30(27,2)3/h12,20-22,24-29,36-37H,11,13-18H2,1-10H3/t20-,21+,22+,24+,25-,26+,27+,28-,29+,32-,33+,34-/m0/s1
SMILES:	CC(=O)OC1CCC2(C3CCC4(C(CC=C4C3(C(CC2C1(C)C)O)C)C5CC(OC5OC)C(C(C)(C)OC)O)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1668610
PubChem CID:	53318272
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001553] Triterpenoids [CHEMONTID:0002380] Limonoids

*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
NPO19151	Chisocheton paniculatus	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19943621]
NPO19151	Chisocheton paniculatus	Species	Meliaceae	Eukaryota	twigs	Xishuangbanna, Yunnan, China	2007-May	PMID[21288727]
NPO19151	Chisocheton paniculatus	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[32208696]
NPO19151	Chisocheton paniculatus	Species	Meliaceae	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
IC50	2

Activity Type	# Activity
Cell Line	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT113	Cell Line	RAW264.7	Mus musculus	IC50	=	6200.0	nM	PMID[483601]
NPT113	Cell Line	RAW264.7	Mus musculus	IC50	>	100000.0	nM	PMID[483601]

☑ 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 NPC470057 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	211
0.1-0.2	1557
0.2-0.3	5146
0.3-0.4	12503
0.4-0.5	9244
0.5-0.6	5789
0.6-0.7	5022
0.7-0.8	2719
0.8-0.85	431
0.85-0.9	63
0.9-0.95	2
0.95-1	10

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC470059
1.0	High Similarity	NPC470064
1.0	High Similarity	NPC470061
1.0	High Similarity	NPC470060
1.0	High Similarity	NPC470043
1.0	High Similarity	NPC470058
1.0	High Similarity	NPC470062
0.9495	High Similarity	NPC470056
0.9495	High Similarity	NPC470055
0.9394	High Similarity	NPC31430
0.9394	High Similarity	NPC85593
0.9286	High Similarity	NPC470054
0.9192	High Similarity	NPC470053
0.9109	High Similarity	NPC473199
0.9082	High Similarity	NPC470068
0.9082	High Similarity	NPC470066
0.9082	High Similarity	NPC470067
0.8942	High Similarity	NPC470065
0.8942	High Similarity	NPC101450
0.8932	High Similarity	NPC38217
0.8932	High Similarity	NPC472988
0.8911	High Similarity	NPC213190
0.8889	High Similarity	NPC216260
0.8889	High Similarity	NPC5358
0.8868	High Similarity	NPC144068
0.8846	High Similarity	NPC154085
0.8846	High Similarity	NPC125361
0.8846	High Similarity	NPC43976
0.8846	High Similarity	NPC296761
0.8846	High Similarity	NPC51925
0.8835	High Similarity	NPC234160
0.8812	High Similarity	NPC136816
0.8713	High Similarity	NPC88000
0.8713	High Similarity	NPC129372
0.8713	High Similarity	NPC309425
0.8713	High Similarity	NPC4831
0.8713	High Similarity	NPC472023
0.8713	High Similarity	NPC47566
0.8713	High Similarity	NPC160734
0.87	High Similarity	NPC234287
0.87	High Similarity	NPC280825
0.8679	High Similarity	NPC114188
0.8679	High Similarity	NPC65167
0.8673	High Similarity	NPC211238
0.8627	High Similarity	NPC154452
0.8614	High Similarity	NPC324598
0.8614	High Similarity	NPC473200
0.8614	High Similarity	NPC7341
0.8586	High Similarity	NPC230347
0.8586	High Similarity	NPC275310
0.8586	High Similarity	NPC286612
0.8571	High Similarity	NPC220427
0.8558	High Similarity	NPC472898
0.8558	High Similarity	NPC472899
0.8558	High Similarity	NPC472900
0.8558	High Similarity	NPC472655
0.8544	High Similarity	NPC155010
0.8544	High Similarity	NPC120123
0.8544	High Similarity	NPC157659
0.8544	High Similarity	NPC189852
0.8544	High Similarity	NPC473020
0.8544	High Similarity	NPC16520
0.8544	High Similarity	NPC211879
0.8544	High Similarity	NPC114874
0.8544	High Similarity	NPC131479
0.8544	High Similarity	NPC286969
0.8544	High Similarity	NPC31907
0.8544	High Similarity	NPC472252
0.8544	High Similarity	NPC245280
0.8544	High Similarity	NPC8039
0.8544	High Similarity	NPC473198
0.8532	High Similarity	NPC212660
0.8529	High Similarity	NPC21064
0.8529	High Similarity	NPC121072
0.8515	High Similarity	NPC477928
0.8491	Intermediate Similarity	NPC218853
0.8491	Intermediate Similarity	NPC206618
0.8485	Intermediate Similarity	NPC178949
0.8485	Intermediate Similarity	NPC96736
0.8476	Intermediate Similarity	NPC226642
0.8468	Intermediate Similarity	NPC161065
0.8468	Intermediate Similarity	NPC304260
0.8468	Intermediate Similarity	NPC268326
0.8468	Intermediate Similarity	NPC29639
0.8468	Intermediate Similarity	NPC5883
0.8468	Intermediate Similarity	NPC44899
0.8468	Intermediate Similarity	NPC153085
0.8468	Intermediate Similarity	NPC477071
0.8462	Intermediate Similarity	NPC470885
0.8462	Intermediate Similarity	NPC187400
0.8462	Intermediate Similarity	NPC173583
0.8462	Intermediate Similarity	NPC221562
0.8462	Intermediate Similarity	NPC475365
0.8462	Intermediate Similarity	NPC165033
0.8462	Intermediate Similarity	NPC273879
0.8455	Intermediate Similarity	NPC93883
0.8447	Intermediate Similarity	NPC288694
0.8447	Intermediate Similarity	NPC312553
0.8447	Intermediate Similarity	NPC159036
0.844	Intermediate Similarity	NPC69576
0.844	Intermediate Similarity	NPC31354
0.844	Intermediate Similarity	NPC84949
0.844	Intermediate Similarity	NPC471633
0.8431	Intermediate Similarity	NPC282669
0.8431	Intermediate Similarity	NPC317019
0.8431	Intermediate Similarity	NPC146188
0.8416	Intermediate Similarity	NPC243728
0.8416	Intermediate Similarity	NPC473555
0.8416	Intermediate Similarity	NPC473890
0.8416	Intermediate Similarity	NPC278939
0.8416	Intermediate Similarity	NPC471770
0.8411	Intermediate Similarity	NPC250956
0.8396	Intermediate Similarity	NPC295389
0.8396	Intermediate Similarity	NPC258323
0.8396	Intermediate Similarity	NPC295980
0.8396	Intermediate Similarity	NPC469845
0.8396	Intermediate Similarity	NPC38948
0.8393	Intermediate Similarity	NPC241192
0.8381	Intermediate Similarity	NPC127801
0.8381	Intermediate Similarity	NPC152584
0.8381	Intermediate Similarity	NPC470767
0.8381	Intermediate Similarity	NPC63023
0.8381	Intermediate Similarity	NPC269627
0.8381	Intermediate Similarity	NPC95243
0.8381	Intermediate Similarity	NPC165405
0.8381	Intermediate Similarity	NPC470763
0.8381	Intermediate Similarity	NPC26798
0.8381	Intermediate Similarity	NPC69737
0.8381	Intermediate Similarity	NPC160816
0.8381	Intermediate Similarity	NPC208477
0.8381	Intermediate Similarity	NPC194842
0.8381	Intermediate Similarity	NPC208594
0.8365	Intermediate Similarity	NPC475701
0.8365	Intermediate Similarity	NPC16573
0.8364	Intermediate Similarity	NPC477031
0.8364	Intermediate Similarity	NPC63609
0.8364	Intermediate Similarity	NPC193382
0.8364	Intermediate Similarity	NPC199428
0.8364	Intermediate Similarity	NPC99620
0.8364	Intermediate Similarity	NPC5311
0.8364	Intermediate Similarity	NPC146652
0.8364	Intermediate Similarity	NPC310341
0.835	Intermediate Similarity	NPC155974
0.8349	Intermediate Similarity	NPC476693
0.8333	Intermediate Similarity	NPC102426
0.8333	Intermediate Similarity	NPC197231
0.8333	Intermediate Similarity	NPC263827
0.8333	Intermediate Similarity	NPC157739
0.8333	Intermediate Similarity	NPC300179
0.8333	Intermediate Similarity	NPC250481
0.8333	Intermediate Similarity	NPC158088
0.8333	Intermediate Similarity	NPC272242
0.8333	Intermediate Similarity	NPC285410
0.8319	Intermediate Similarity	NPC475219
0.8319	Intermediate Similarity	NPC231518
0.8318	Intermediate Similarity	NPC476835
0.8318	Intermediate Similarity	NPC472901
0.8318	Intermediate Similarity	NPC477069
0.8318	Intermediate Similarity	NPC477070
0.8317	Intermediate Similarity	NPC471903
0.8317	Intermediate Similarity	NPC472989
0.8304	Intermediate Similarity	NPC236973
0.8304	Intermediate Similarity	NPC469756
0.8304	Intermediate Similarity	NPC32177
0.8304	Intermediate Similarity	NPC55532
0.8304	Intermediate Similarity	NPC30483
0.8304	Intermediate Similarity	NPC470897
0.8304	Intermediate Similarity	NPC292467
0.8302	Intermediate Similarity	NPC63368
0.8302	Intermediate Similarity	NPC293512
0.8302	Intermediate Similarity	NPC14946
0.8302	Intermediate Similarity	NPC473469
0.8302	Intermediate Similarity	NPC231340
0.8302	Intermediate Similarity	NPC208650
0.8302	Intermediate Similarity	NPC190395
0.8302	Intermediate Similarity	NPC181467
0.8288	Intermediate Similarity	NPC99728
0.8288	Intermediate Similarity	NPC50305
0.8288	Intermediate Similarity	NPC77319
0.8288	Intermediate Similarity	NPC157376
0.8288	Intermediate Similarity	NPC471353
0.8288	Intermediate Similarity	NPC27507
0.8288	Intermediate Similarity	NPC471351
0.8288	Intermediate Similarity	NPC473852
0.8288	Intermediate Similarity	NPC471354
0.8288	Intermediate Similarity	NPC244402
0.8288	Intermediate Similarity	NPC152615
0.8288	Intermediate Similarity	NPC309034
0.8288	Intermediate Similarity	NPC243196
0.8288	Intermediate Similarity	NPC203862
0.8288	Intermediate Similarity	NPC87250
0.8288	Intermediate Similarity	NPC34390
0.8288	Intermediate Similarity	NPC142066
0.8288	Intermediate Similarity	NPC477807
0.8288	Intermediate Similarity	NPC196429
0.8288	Intermediate Similarity	NPC474418
0.8288	Intermediate Similarity	NPC158344
0.8288	Intermediate Similarity	NPC290693
0.8288	Intermediate Similarity	NPC471355
0.8288	Intermediate Similarity	NPC84987

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 NPC470057 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	1813
0.2-0.3	4103
0.3-0.4	2026
0.4-0.5	553
0.5-0.6	264
0.6-0.7	185
0.7-0.8	20
0.8-0.85	11
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8319	Intermediate Similarity	NPD8033	Approved
0.823	Intermediate Similarity	NPD8377	Approved
0.823	Intermediate Similarity	NPD8294	Approved
0.8214	Intermediate Similarity	NPD7328	Approved
0.8214	Intermediate Similarity	NPD7327	Approved
0.8158	Intermediate Similarity	NPD8296	Approved
0.8158	Intermediate Similarity	NPD8335	Approved
0.8158	Intermediate Similarity	NPD8378	Approved
0.8158	Intermediate Similarity	NPD8380	Approved
0.8158	Intermediate Similarity	NPD8379	Approved
0.8142	Intermediate Similarity	NPD7516	Approved
0.775	Intermediate Similarity	NPD7736	Approved
0.7731	Intermediate Similarity	NPD7507	Approved
0.7667	Intermediate Similarity	NPD8293	Discontinued
0.7658	Intermediate Similarity	NPD8132	Clinical (unspecified phase)
0.7544	Intermediate Similarity	NPD8133	Approved
0.7542	Intermediate Similarity	NPD7503	Approved
0.7541	Intermediate Similarity	NPD7319	Approved
0.75	Intermediate Similarity	NPD8295	Clinical (unspecified phase)
0.7479	Intermediate Similarity	NPD6370	Approved
0.7477	Intermediate Similarity	NPD6412	Phase 2
0.7411	Intermediate Similarity	NPD6686	Approved
0.7355	Intermediate Similarity	NPD7492	Approved
0.7347	Intermediate Similarity	NPD7525	Registered
0.7333	Intermediate Similarity	NPD8171	Discontinued
0.7315	Intermediate Similarity	NPD7638	Approved
0.7311	Intermediate Similarity	NPD6059	Approved
0.7311	Intermediate Similarity	NPD6054	Approved
0.7295	Intermediate Similarity	NPD6616	Approved
0.7273	Intermediate Similarity	NPD8328	Phase 3
0.7248	Intermediate Similarity	NPD7640	Approved
0.7248	Intermediate Similarity	NPD7639	Approved
0.7236	Intermediate Similarity	NPD7078	Approved
0.7107	Intermediate Similarity	NPD6016	Approved
0.7107	Intermediate Similarity	NPD6015	Approved
0.7059	Intermediate Similarity	NPD6009	Approved
0.7049	Intermediate Similarity	NPD5988	Approved
0.7019	Intermediate Similarity	NPD7524	Approved
0.7009	Intermediate Similarity	NPD6399	Phase 3
0.7009	Intermediate Similarity	NPD8297	Approved
0.7009	Intermediate Similarity	NPD6882	Approved
0.7	Intermediate Similarity	NPD4225	Approved
0.6992	Remote Similarity	NPD6067	Discontinued
0.6991	Remote Similarity	NPD8170	Clinical (unspecified phase)
0.6957	Remote Similarity	NPD7320	Approved
0.6949	Remote Similarity	NPD4632	Approved
0.693	Remote Similarity	NPD6008	Approved
0.693	Remote Similarity	NPD7128	Approved
0.693	Remote Similarity	NPD6402	Approved
0.693	Remote Similarity	NPD6675	Approved
0.693	Remote Similarity	NPD5739	Approved
0.6916	Remote Similarity	NPD8035	Phase 2
0.6916	Remote Similarity	NPD8034	Phase 2
0.6897	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6893	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6885	Remote Similarity	NPD6319	Approved
0.6832	Remote Similarity	NPD6928	Phase 2
0.6829	Remote Similarity	NPD8517	Approved
0.6829	Remote Similarity	NPD8515	Approved
0.6829	Remote Similarity	NPD8516	Approved
0.6829	Remote Similarity	NPD8513	Phase 3
0.6814	Remote Similarity	NPD7632	Discontinued
0.681	Remote Similarity	NPD6881	Approved
0.681	Remote Similarity	NPD6899	Approved
0.6796	Remote Similarity	NPD6695	Phase 3
0.6789	Remote Similarity	NPD7748	Approved
0.678	Remote Similarity	NPD8130	Phase 1
0.6777	Remote Similarity	NPD7115	Discovery
0.6772	Remote Similarity	NPD6033	Approved
0.6757	Remote Similarity	NPD7902	Approved
0.6752	Remote Similarity	NPD6372	Approved
0.6752	Remote Similarity	NPD6373	Approved
0.6733	Remote Similarity	NPD7645	Phase 2
0.6726	Remote Similarity	NPD5344	Discontinued
0.6724	Remote Similarity	NPD5697	Approved
0.6724	Remote Similarity	NPD5701	Approved
0.6698	Remote Similarity	NPD7750	Discontinued
0.6695	Remote Similarity	NPD6883	Approved
0.6695	Remote Similarity	NPD7290	Approved
0.6695	Remote Similarity	NPD7102	Approved
0.6692	Remote Similarity	NPD8449	Approved
0.6667	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6942	Approved
0.6667	Remote Similarity	NPD7339	Approved
0.6667	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6641	Remote Similarity	NPD8450	Suspended
0.6639	Remote Similarity	NPD6650	Approved
0.6639	Remote Similarity	NPD6869	Approved
0.6639	Remote Similarity	NPD6617	Approved
0.6639	Remote Similarity	NPD6649	Approved
0.6639	Remote Similarity	NPD6847	Approved
0.661	Remote Similarity	NPD6013	Approved
0.661	Remote Similarity	NPD6012	Approved
0.661	Remote Similarity	NPD6014	Approved
0.6607	Remote Similarity	NPD6084	Phase 2
0.6607	Remote Similarity	NPD6083	Phase 2
0.6606	Remote Similarity	NPD7515	Phase 2
0.6606	Remote Similarity	NPD7637	Suspended
0.66	Remote Similarity	NPD6933	Approved
0.6587	Remote Similarity	NPD7604	Phase 2
0.6571	Remote Similarity	NPD4786	Approved
0.656	Remote Similarity	NPD5983	Phase 2
0.6555	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6547	Remote Similarity	NPD7625	Phase 1
0.6525	Remote Similarity	NPD6011	Approved
0.6505	Remote Similarity	NPD6931	Approved
0.6505	Remote Similarity	NPD6930	Phase 2
0.6505	Remote Similarity	NPD7509	Discontinued
0.65	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.65	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6495	Remote Similarity	NPD4267	Clinical (unspecified phase)
0.6486	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6486	Remote Similarity	NPD7900	Approved
0.6484	Remote Similarity	NPD6336	Discontinued
0.6471	Remote Similarity	NPD6118	Approved
0.6471	Remote Similarity	NPD6114	Approved
0.6471	Remote Similarity	NPD6697	Approved
0.6471	Remote Similarity	NPD6115	Approved
0.646	Remote Similarity	NPD4755	Approved
0.6436	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.6429	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6422	Remote Similarity	NPD5328	Approved
0.6422	Remote Similarity	NPD6051	Approved
0.6417	Remote Similarity	NPD4634	Approved
0.6408	Remote Similarity	NPD6929	Approved
0.64	Remote Similarity	NPD6926	Approved
0.64	Remote Similarity	NPD6924	Approved
0.6396	Remote Similarity	NPD4202	Approved
0.6389	Remote Similarity	NPD4751	Clinical (unspecified phase)
0.6381	Remote Similarity	NPD3667	Approved
0.6373	Remote Similarity	NPD6116	Phase 1
0.6373	Remote Similarity	NPD6932	Approved
0.6364	Remote Similarity	NPD3168	Discontinued
0.6348	Remote Similarity	NPD5286	Approved
0.6348	Remote Similarity	NPD4696	Approved
0.6348	Remote Similarity	NPD5285	Approved
0.6348	Remote Similarity	NPD6648	Approved
0.6348	Remote Similarity	NPD4700	Approved
0.6346	Remote Similarity	NPD7332	Phase 2
0.6321	Remote Similarity	NPD3670	Clinical (unspecified phase)
0.6321	Remote Similarity	NPD3669	Approved
0.6311	Remote Similarity	NPD6053	Discontinued
0.6308	Remote Similarity	NPD8074	Phase 3
0.6306	Remote Similarity	NPD7087	Discontinued
0.6306	Remote Similarity	NPD6079	Approved
0.6303	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6303	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6296	Remote Similarity	NPD3618	Phase 1
0.629	Remote Similarity	NPD6940	Discontinued
0.629	Remote Similarity	NPD6274	Approved
0.6288	Remote Similarity	NPD5956	Approved
0.6286	Remote Similarity	NPD6898	Phase 1
0.6283	Remote Similarity	NPD5695	Phase 3
0.6275	Remote Similarity	NPD6117	Approved
0.627	Remote Similarity	NPD7100	Approved
0.627	Remote Similarity	NPD7101	Approved
0.6262	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6261	Remote Similarity	NPD5696	Approved
0.6261	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.625	Remote Similarity	NPD6683	Phase 2
0.6239	Remote Similarity	NPD5224	Approved
0.6239	Remote Similarity	NPD5211	Phase 2
0.6239	Remote Similarity	NPD5226	Approved
0.6239	Remote Similarity	NPD5225	Approved
0.6239	Remote Similarity	NPD4633	Approved
0.6238	Remote Similarity	NPD1811	Approved
0.6238	Remote Similarity	NPD1810	Approved
0.6216	Remote Similarity	NPD7838	Discovery
0.6214	Remote Similarity	NPD5776	Phase 2
0.6214	Remote Similarity	NPD6925	Approved
0.6204	Remote Similarity	NPD6893	Approved
0.619	Remote Similarity	NPD4748	Discontinued
0.619	Remote Similarity	NPD7514	Phase 3
0.619	Remote Similarity	NPD6335	Approved
0.6186	Remote Similarity	NPD5175	Approved
0.6186	Remote Similarity	NPD5174	Approved
0.6182	Remote Similarity	NPD5737	Approved
0.6182	Remote Similarity	NPD6672	Approved
0.6182	Remote Similarity	NPD6903	Approved
0.6182	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6172	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.6172	Remote Similarity	NPD6908	Approved
0.6172	Remote Similarity	NPD6909	Approved
0.6161	Remote Similarity	NPD6411	Approved
0.6154	Remote Similarity	NPD4159	Approved
0.6154	Remote Similarity	NPD7145	Approved
0.6154	Remote Similarity	NPD5223	Approved
0.6148	Remote Similarity	NPD6371	Approved
0.6147	Remote Similarity	NPD5330	Approved
0.6147	Remote Similarity	NPD6684	Approved
0.6147	Remote Similarity	NPD7146	Approved
0.6147	Remote Similarity	NPD7521	Approved
0.6147	Remote Similarity	NPD6409	Approved
0.6147	Remote Similarity	NPD7334	Approved
0.614	Remote Similarity	NPD7991	Discontinued
0.6134	Remote Similarity	NPD5141	Approved
0.6126	Remote Similarity	NPD4753	Phase 2
0.6111	Remote Similarity	NPD6317	Approved
0.61	Remote Similarity	NPD7532	Clinical (unspecified phase)
0.6091	Remote Similarity	NPD4250	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