NPASS Compound

Structure

NPC475066 OpenBabel07101718312D 42 47 0 0 1 0 0 0 0 0999 V2000 -3.4188 3.0515 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6720 4.0255 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7453 1.2364 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.7665 1.4782 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4053 2.0565 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9123 -1.0095 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4204 -0.9074 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5604 2.5386 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8143 0.9087 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.8143 0.9087 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2453 -1.3024 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9927 -1.5038 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1553 0.3215 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3143 -0.6301 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1069 2.5514 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6870 3.0256 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7453 0.2364 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8721 1.0309 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5053 -0.0424 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5543 -0.3514 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.2453 -1.3024 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8584 -0.5129 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.5272 -0.1950 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.1431 1.1345 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.3016 -2.2266 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9362 -0.3514 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8884 1.4869 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.7468 0.9740 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0150 0.9999 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8285 2.5127 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4999 1.6319 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.7319 -0.0259 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 4.8123 0.0327 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.7643 -1.1665 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.6530 -3.1629 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0449 2.9997 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.1234 -0.0424 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.1109 2.4618 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.0375 1.5818 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.6944 -2.1370 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8435 1.5128 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 8 1 0 0 0 0 2 16 1 0 0 0 0 3 17 1 0 0 0 0 4 18 1 0 0 0 0 8 16 2 0 0 0 0 9 10 2 0 0 0 0 9 19 1 0 0 0 0 10 38 1 0 0 0 0 11 20 1 0 0 0 0 12 22 1 0 0 0 0 12 25 1 0 0 0 0 13 23 1 0 0 0 0 13 24 1 0 0 0 0 14 19 2 0 0 0 0 14 38 1 0 0 0 0 15 31 1 0 0 0 0 15 39 1 0 0 0 0 16 30 1 0 0 0 0 17 20 1 0 0 0 0 17 26 2 0 0 0 0 18 34 2 0 0 0 0 18 40 1 0 0 0 0 20 19 1 1 0 0 0 21 11 1 1 0 0 0 21 26 1 0 0 0 0 21 41 1 0 0 0 0 22 32 1 1 0 0 0 22 33 1 0 0 0 0 23 32 1 6 0 0 0 23 35 1 0 0 0 0 24 31 1 6 0 0 0 24 40 1 0 0 0 0 25 36 2 0 0 0 0 25 41 1 0 0 0 0 26 33 1 0 0 0 0 27 28 1 0 0 0 0 27 29 1 0 0 0 0 27 39 1 6 0 0 0 28 31 1 1 0 0 0 28 32 1 0 0 0 0 29 33 1 6 0 0 0 29 42 1 0 0 0 0 30 37 2 0 0 0 0 30 42 1 0 0 0 0 31 5 1 1 0 0 0 32 6 1 1 0 0 0 33 7 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	582.28
Volume:	588.642
LogP:	3.446
LogD:	2.828
LogS:	-4.636
# Rotatable Bonds:	6
TPSA:	121.5
# H-Bond Aceptor:	9
# H-Bond Donor:	1
# Rings:	6
# Heavy Atoms:	9

MedChem Properties

QED Drug-Likeness Score:	0.234
Synthetic Accessibility Score:	5.634
Fsp3:	0.667
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:	-5.084
MDCK Permeability:	5.399300061981194e-05
Pgp-inhibitor:	1.0
Pgp-substrate:	0.998
Human Intestinal Absorption (HIA):	0.013
20% Bioavailability (F20%):	0.336
30% Bioavailability (F30%):	0.929

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.118
Plasma Protein Binding (PPB):	90.54485321044922%
Volume Distribution (VD):	2.833
Pgp-substrate:	6.689882278442383%

ADMET: Metabolism

CYP1A2-inhibitor:	0.024
CYP1A2-substrate:	0.081
CYP2C19-inhibitor:	0.419
CYP2C19-substrate:	0.167
CYP2C9-inhibitor:	0.832
CYP2C9-substrate:	0.032
CYP2D6-inhibitor:	0.032
CYP2D6-substrate:	0.081
CYP3A4-inhibitor:	0.911
CYP3A4-substrate:	0.585

ADMET: Excretion

Clearance (CL):	6.601
Half-life (T1/2):	0.722

ADMET: Toxicity

hERG Blockers:	0.79
Human Hepatotoxicity (H-HT):	0.958
Drug-inuced Liver Injury (DILI):	0.892
AMES Toxicity:	0.01
Rat Oral Acute Toxicity:	0.909
Maximum Recommended Daily Dose:	0.996
Skin Sensitization:	0.107
Carcinogencity:	0.013
Eye Corrosion:	0.004
Eye Irritation:	0.028
Respiratory Toxicity:	0.966

Download Data

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

Natural Product: NPC475066

Natural Product ID:	NPC475066
*Common Name:**	1-O-Deacetylohchinolide B
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	LHFRBMWFNLUYCY-ABMVXICKSA-N
Standard InCHI:	InChI=1S/C33H42O9/c1-8-16(2)30(37)42-29-27-28-31(5,15-39-27)24(40-18(4)34)13-23(35)32(28,6)22-12-25(36)41-21-11-20(19-9-10-38-14-19)17(3)26(21)33(22,29)7/h8-10,14,20-24,27-29,35H,11-13,15H2,1-7H3/b16-8+/t20-,21+,22-,23+,24-,27-,28+,29-,31-,32+,33-/m1/s1
SMILES:	C/C=C(/C(=O)O[C@@H]1[C@@H]2OC[C@]3([C@H]2[C@]([C@@H]2[C@]1(C)C1=C(C)[C@@H](C[C@@H]1OC(=O)C2)c1ccoc1)(C)[C@H](C[C@H]3OC(=O)C)O)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL495473
PubChem CID:	11421886
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
NPO18932	Melia azedarach	Species	Meliaceae	Eukaryota	n.a.	Brazilian	n.a.	PMID[15387656]
NPO18932	Melia azedarach	Species	Meliaceae	Eukaryota	n.a.	ripe fruit	n.a.	PMID[16205005]
NPO18932	Melia azedarach	Species	Meliaceae	Eukaryota	Fruits	n.a.	n.a.	PMID[33253570]
NPO18932	Melia azedarach	Species	Meliaceae	Eukaryota	Seeds	n.a.	n.a.	PMID[3701342]
NPO18932	Melia azedarach	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO18932	Melia azedarach	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO18932	Melia azedarach	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO18932	Melia azedarach	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO18932	Melia azedarach	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	1
Others	1

Activity Type	# Activity
NON-MOLECULAR	1
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT140	Organism	Artemia	Artemia	Activity	=	100.0	%	PMID[464829]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	100.0	nM	PMID[464829]

☑ 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 NPC475066 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	331
0.1-0.2	1234
0.2-0.3	3004
0.3-0.4	5272
0.4-0.5	10392
0.5-0.6	10789
0.6-0.7	10102
0.7-0.8	1161
0.8-0.85	286
0.85-0.9	95
0.9-0.95	24
0.95-1	7

Similarity Score	Similarity Level	Natural Product ID
0.98	High Similarity	NPC472671
0.9733	High Similarity	NPC470119
0.9733	High Similarity	NPC214495
0.973	High Similarity	NPC29695
0.973	High Similarity	NPC182427
0.9669	High Similarity	NPC475226
0.961	High Similarity	NPC307781
0.961	High Similarity	NPC472670
0.9467	High Similarity	NPC322546
0.9467	High Similarity	NPC308205
0.9427	High Similarity	NPC118086
0.9416	High Similarity	NPC470792
0.9363	High Similarity	NPC472673
0.9338	High Similarity	NPC472672
0.9276	High Similarity	NPC98206
0.9276	High Similarity	NPC34421
0.9276	High Similarity	NPC253201
0.9276	High Similarity	NPC237259
0.9276	High Similarity	NPC302054
0.9226	High Similarity	NPC470789
0.9221	High Similarity	NPC197137
0.9221	High Similarity	NPC470118
0.9172	High Similarity	NPC27541
0.9172	High Similarity	NPC62692
0.9172	High Similarity	NPC126984
0.9139	High Similarity	NPC69647
0.9139	High Similarity	NPC125182
0.9133	High Similarity	NPC255414
0.9125	High Similarity	NPC475641
0.9125	High Similarity	NPC475237
0.9091	High Similarity	NPC296807
0.9091	High Similarity	NPC141538
0.9091	High Similarity	NPC155939
0.908	High Similarity	NPC11062
0.902	High Similarity	NPC116717
0.9013	High Similarity	NPC472654
0.9013	High Similarity	NPC470791
0.9013	High Similarity	NPC470790
0.8974	High Similarity	NPC469847
0.8961	High Similarity	NPC268905
0.8947	High Similarity	NPC471007
0.8931	High Similarity	NPC61967
0.8924	High Similarity	NPC472771
0.8889	High Similarity	NPC471001
0.8889	High Similarity	NPC195325
0.8889	High Similarity	NPC285227
0.8882	High Similarity	NPC216755
0.8882	High Similarity	NPC472652
0.8882	High Similarity	NPC471174
0.8875	High Similarity	NPC472141
0.8874	High Similarity	NPC5676
0.8868	High Similarity	NPC472773
0.8868	High Similarity	NPC472669
0.8854	High Similarity	NPC472776
0.8854	High Similarity	NPC472778
0.8854	High Similarity	NPC472777
0.8846	High Similarity	NPC92979
0.8839	High Similarity	NPC33938
0.8831	High Similarity	NPC196846
0.8831	High Similarity	NPC156189
0.8831	High Similarity	NPC470997
0.882	High Similarity	NPC472651
0.882	High Similarity	NPC310572
0.882	High Similarity	NPC472764
0.8808	High Similarity	NPC251865
0.88	High Similarity	NPC121158
0.8797	High Similarity	NPC475967
0.8774	High Similarity	NPC291150
0.8774	High Similarity	NPC18135
0.8766	High Similarity	NPC234494
0.8765	High Similarity	NPC472765
0.8765	High Similarity	NPC472766
0.875	High Similarity	NPC471168
0.875	High Similarity	NPC472139
0.8734	High Similarity	NPC195954
0.8734	High Similarity	NPC88007
0.8734	High Similarity	NPC472772
0.8734	High Similarity	NPC194499
0.8734	High Similarity	NPC299038
0.8734	High Similarity	NPC167142
0.8718	High Similarity	NPC469503
0.8712	High Similarity	NPC472659
0.871	High Similarity	NPC5180
0.8704	High Similarity	NPC472775
0.8704	High Similarity	NPC472774
0.8693	High Similarity	NPC470999
0.8688	High Similarity	NPC472767
0.8688	High Similarity	NPC200782
0.8688	High Similarity	NPC472668
0.8688	High Similarity	NPC471167
0.8688	High Similarity	NPC471166
0.8667	High Similarity	NPC67003
0.8667	High Similarity	NPC471632
0.865	High Similarity	NPC271235
0.8634	High Similarity	NPC283209
0.8634	High Similarity	NPC285567
0.8625	High Similarity	NPC472653
0.8616	High Similarity	NPC45101
0.8608	High Similarity	NPC476262
0.8599	High Similarity	NPC476201
0.8599	High Similarity	NPC294511
0.8599	High Similarity	NPC121615
0.8599	High Similarity	NPC470996
0.8599	High Similarity	NPC471002
0.8598	High Similarity	NPC470995
0.858	High Similarity	NPC259943
0.8571	High Similarity	NPC82851
0.8571	High Similarity	NPC68848
0.8571	High Similarity	NPC5741
0.8571	High Similarity	NPC470938
0.8562	High Similarity	NPC84349
0.8554	High Similarity	NPC94763
0.8544	High Similarity	NPC282445
0.8535	High Similarity	NPC471000
0.8529	High Similarity	NPC242068
0.8529	High Similarity	NPC247563
0.8529	High Similarity	NPC105395
0.8528	High Similarity	NPC93172
0.8528	High Similarity	NPC470875
0.8528	High Similarity	NPC97574
0.8526	High Similarity	NPC470998
0.8519	High Similarity	NPC469846
0.8519	High Similarity	NPC165218
0.8519	High Similarity	NPC302369
0.8519	High Similarity	NPC134254
0.8519	High Similarity	NPC39986
0.8516	High Similarity	NPC221809
0.8509	High Similarity	NPC191828
0.8506	High Similarity	NPC34056
0.85	High Similarity	NPC304692
0.85	High Similarity	NPC261597
0.85	High Similarity	NPC36655
0.8497	Intermediate Similarity	NPC243577
0.8494	Intermediate Similarity	NPC469848
0.8491	Intermediate Similarity	NPC44675
0.8491	Intermediate Similarity	NPC214541
0.8491	Intermediate Similarity	NPC469336
0.8485	Intermediate Similarity	NPC82602
0.8481	Intermediate Similarity	NPC84063
0.8481	Intermediate Similarity	NPC75906
0.8481	Intermediate Similarity	NPC246164
0.8477	Intermediate Similarity	NPC90953
0.8476	Intermediate Similarity	NPC476853
0.8476	Intermediate Similarity	NPC476224
0.8476	Intermediate Similarity	NPC476850
0.8476	Intermediate Similarity	NPC476861
0.8476	Intermediate Similarity	NPC100333
0.8471	Intermediate Similarity	NPC212257
0.8466	Intermediate Similarity	NPC469849
0.8466	Intermediate Similarity	NPC276551
0.8466	Intermediate Similarity	NPC123088
0.8466	Intermediate Similarity	NPC470182
0.8457	Intermediate Similarity	NPC471003
0.8457	Intermediate Similarity	NPC329938
0.8457	Intermediate Similarity	NPC79571
0.8457	Intermediate Similarity	NPC69028
0.8457	Intermediate Similarity	NPC188649
0.8447	Intermediate Similarity	NPC307383
0.8447	Intermediate Similarity	NPC472779
0.8443	Intermediate Similarity	NPC471437
0.8443	Intermediate Similarity	NPC236004
0.8438	Intermediate Similarity	NPC41880
0.8438	Intermediate Similarity	NPC471169
0.8438	Intermediate Similarity	NPC204663
0.8438	Intermediate Similarity	NPC104736
0.8438	Intermediate Similarity	NPC175964
0.8428	Intermediate Similarity	NPC178932
0.8428	Intermediate Similarity	NPC57998
0.8424	Intermediate Similarity	NPC160651
0.8424	Intermediate Similarity	NPC471397
0.8424	Intermediate Similarity	NPC327922
0.8421	Intermediate Similarity	NPC56197
0.8418	Intermediate Similarity	NPC272590
0.8415	Intermediate Similarity	NPC214600
0.8415	Intermediate Similarity	NPC149945
0.8415	Intermediate Similarity	NPC121995
0.8405	Intermediate Similarity	NPC477405
0.8405	Intermediate Similarity	NPC292389
0.8405	Intermediate Similarity	NPC88841
0.8405	Intermediate Similarity	NPC469338
0.8405	Intermediate Similarity	NPC288602
0.8397	Intermediate Similarity	NPC302987
0.8397	Intermediate Similarity	NPC71821
0.8397	Intermediate Similarity	NPC470941
0.8397	Intermediate Similarity	NPC250228
0.8395	Intermediate Similarity	NPC8389
0.8395	Intermediate Similarity	NPC335761
0.8393	Intermediate Similarity	NPC469633
0.8385	Intermediate Similarity	NPC195131
0.8385	Intermediate Similarity	NPC249021
0.8385	Intermediate Similarity	NPC187149
0.8377	Intermediate Similarity	NPC80635
0.8377	Intermediate Similarity	NPC223415
0.8375	Intermediate Similarity	NPC264943
0.8375	Intermediate Similarity	NPC471175
0.8375	Intermediate Similarity	NPC35000
0.8373	Intermediate Similarity	NPC472650
0.8364	Intermediate Similarity	NPC173516
0.8364	Intermediate Similarity	NPC472282
0.8364	Intermediate Similarity	NPC478179

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 NPC475066 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	275
0.1-0.2	910
0.2-0.3	2096
0.3-0.4	2718
0.4-0.5	1946
0.5-0.6	933
0.6-0.7	257
0.7-0.8	13
0.8-0.85	2
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8375	Intermediate Similarity	NPD5761	Phase 2
0.8375	Intermediate Similarity	NPD5760	Phase 2
0.8046	Intermediate Similarity	NPD8434	Phase 2
0.7759	Intermediate Similarity	NPD6764	Approved
0.7759	Intermediate Similarity	NPD6765	Approved
0.7625	Intermediate Similarity	NPD4628	Phase 3
0.7584	Intermediate Similarity	NPD6785	Approved
0.7584	Intermediate Similarity	NPD6784	Approved
0.7442	Intermediate Similarity	NPD8127	Discontinued
0.7427	Intermediate Similarity	NPD5537	Clinical (unspecified phase)
0.7294	Intermediate Similarity	NPD7819	Suspended
0.7293	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7289	Intermediate Similarity	NPD6273	Approved
0.7191	Intermediate Similarity	NPD5844	Phase 1
0.7167	Intermediate Similarity	NPD6559	Discontinued
0.7118	Intermediate Similarity	NPD6599	Discontinued
0.7117	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.711	Intermediate Similarity	NPD4966	Approved
0.711	Intermediate Similarity	NPD4965	Approved
0.711	Intermediate Similarity	NPD4967	Phase 2
0.7093	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7069	Intermediate Similarity	NPD7075	Discontinued
0.7045	Intermediate Similarity	NPD7199	Phase 2
0.7024	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7012	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.7012	Intermediate Similarity	NPD6004	Phase 3
0.7012	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.7012	Intermediate Similarity	NPD6005	Phase 3
0.7012	Intermediate Similarity	NPD6002	Phase 3
0.7011	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD8404	Phase 2
0.6944	Remote Similarity	NPD7799	Discontinued
0.6941	Remote Similarity	NPD920	Approved
0.6936	Remote Similarity	NPD37	Approved
0.6936	Remote Similarity	NPD6801	Discontinued
0.6932	Remote Similarity	NPD6234	Discontinued
0.6932	Remote Similarity	NPD919	Approved
0.6928	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6909	Remote Similarity	NPD5762	Approved
0.6909	Remote Similarity	NPD5763	Approved
0.6905	Remote Similarity	NPD7236	Approved
0.6893	Remote Similarity	NPD5494	Approved
0.689	Remote Similarity	NPD2799	Discontinued
0.6889	Remote Similarity	NPD7473	Discontinued
0.6886	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6885	Remote Similarity	NPD7685	Pre-registration
0.6872	Remote Similarity	NPD7184	Clinical (unspecified phase)
0.6864	Remote Similarity	NPD6799	Approved
0.686	Remote Similarity	NPD7458	Discontinued
0.6857	Remote Similarity	NPD3817	Phase 2
0.6857	Remote Similarity	NPD8443	Clinical (unspecified phase)
0.6851	Remote Similarity	NPD3818	Discontinued
0.6851	Remote Similarity	NPD7228	Approved
0.6832	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6831	Remote Similarity	NPD7993	Clinical (unspecified phase)
0.6824	Remote Similarity	NPD642	Clinical (unspecified phase)
0.6824	Remote Similarity	NPD2533	Approved
0.6824	Remote Similarity	NPD2534	Approved
0.6824	Remote Similarity	NPD2532	Approved
0.6821	Remote Similarity	NPD4380	Phase 2
0.6821	Remote Similarity	NPD7497	Discontinued
0.6816	Remote Similarity	NPD6232	Discontinued
0.6811	Remote Similarity	NPD8312	Approved
0.6811	Remote Similarity	NPD8313	Approved
0.681	Remote Similarity	NPD6355	Discontinued
0.6805	Remote Similarity	NPD643	Clinical (unspecified phase)
0.6802	Remote Similarity	NPD7239	Suspended
0.68	Remote Similarity	NPD2393	Clinical (unspecified phase)
0.6792	Remote Similarity	NPD6007	Clinical (unspecified phase)
0.6786	Remote Similarity	NPD4109	Clinical (unspecified phase)
0.6786	Remote Similarity	NPD4110	Phase 3
0.6782	Remote Similarity	NPD7411	Suspended
0.678	Remote Similarity	NPD4381	Clinical (unspecified phase)
0.6765	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6763	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6763	Remote Similarity	NPD3226	Approved
0.6752	Remote Similarity	NPD1608	Approved
0.6748	Remote Similarity	NPD4140	Approved
0.6747	Remote Similarity	NPD1551	Phase 2
0.6744	Remote Similarity	NPD6980	Clinical (unspecified phase)
0.6743	Remote Similarity	NPD1934	Approved
0.6737	Remote Similarity	NPD7879	Clinical (unspecified phase)
0.6723	Remote Similarity	NPD7768	Phase 2
0.6723	Remote Similarity	NPD3882	Suspended
0.6721	Remote Similarity	NPD7804	Clinical (unspecified phase)
0.6705	Remote Similarity	NPD8455	Phase 2
0.6703	Remote Similarity	NPD7240	Approved
0.6687	Remote Similarity	NPD8032	Phase 2
0.6686	Remote Similarity	NPD3750	Approved
0.6685	Remote Similarity	NPD3749	Approved
0.6685	Remote Similarity	NPD7074	Phase 3
0.6667	Remote Similarity	NPD7893	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD1247	Approved
0.6667	Remote Similarity	NPD5402	Approved
0.6667	Remote Similarity	NPD970	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6653	Approved
0.6648	Remote Similarity	NPD6167	Clinical (unspecified phase)
0.6648	Remote Similarity	NPD7852	Clinical (unspecified phase)
0.6648	Remote Similarity	NPD6168	Clinical (unspecified phase)
0.6648	Remote Similarity	NPD6166	Phase 2
0.6647	Remote Similarity	NPD6100	Approved
0.6647	Remote Similarity	NPD2796	Approved
0.6647	Remote Similarity	NPD5403	Approved
0.6647	Remote Similarity	NPD6099	Approved
0.663	Remote Similarity	NPD7229	Phase 3
0.663	Remote Similarity	NPD7054	Approved
0.6628	Remote Similarity	NPD4378	Clinical (unspecified phase)
0.6628	Remote Similarity	NPD5401	Approved
0.6627	Remote Similarity	NPD1243	Approved
0.661	Remote Similarity	NPD1465	Phase 2
0.6607	Remote Similarity	NPD2346	Discontinued
0.6607	Remote Similarity	NPD1471	Phase 3
0.6606	Remote Similarity	NPD5735	Approved
0.6605	Remote Similarity	NPD6832	Phase 2
0.6596	Remote Similarity	NPD8407	Phase 2
0.6595	Remote Similarity	NPD7472	Approved
0.6593	Remote Similarity	NPD3926	Phase 2
0.659	Remote Similarity	NPD7314	Clinical (unspecified phase)
0.6588	Remote Similarity	NPD7003	Approved
0.6587	Remote Similarity	NPD3748	Approved
0.6587	Remote Similarity	NPD7033	Discontinued
0.6578	Remote Similarity	NPD7808	Phase 3
0.6575	Remote Similarity	NPD6959	Discontinued
0.6568	Remote Similarity	NPD1549	Phase 2
0.6561	Remote Similarity	NPD17	Approved
0.6548	Remote Similarity	NPD2935	Discontinued
0.6548	Remote Similarity	NPD2438	Suspended
0.6545	Remote Similarity	NPD8397	Clinical (unspecified phase)
0.6538	Remote Similarity	NPD7315	Approved
0.6534	Remote Similarity	NPD7028	Phase 2
0.6529	Remote Similarity	NPD2800	Approved
0.6526	Remote Similarity	NPD8150	Discontinued
0.6524	Remote Similarity	NPD7251	Discontinued
0.6524	Remote Similarity	NPD8368	Discontinued
0.6517	Remote Similarity	NPD2801	Approved
0.6509	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.6509	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6509	Remote Similarity	NPD2344	Approved
0.6491	Remote Similarity	NPD8166	Discontinued
0.6489	Remote Similarity	NPD4338	Clinical (unspecified phase)
0.6485	Remote Similarity	NPD6663	Approved
0.6471	Remote Similarity	NPD6797	Phase 2
0.6463	Remote Similarity	NPD5952	Clinical (unspecified phase)
0.6456	Remote Similarity	NPD1778	Approved
0.6453	Remote Similarity	NPD6190	Approved
0.6452	Remote Similarity	NPD8470	Clinical (unspecified phase)
0.645	Remote Similarity	NPD4477	Approved
0.645	Remote Similarity	NPD4476	Approved
0.6444	Remote Similarity	NPD7057	Phase 3
0.6444	Remote Similarity	NPD7058	Phase 2
0.6438	Remote Similarity	NPD3972	Approved
0.6437	Remote Similarity	NPD7410	Clinical (unspecified phase)
0.6429	Remote Similarity	NPD7097	Phase 1
0.6424	Remote Similarity	NPD6798	Discontinued
0.6424	Remote Similarity	NPD3268	Approved
0.6424	Remote Similarity	NPD3764	Approved
0.6424	Remote Similarity	NPD1699	Clinical (unspecified phase)
0.6424	Remote Similarity	NPD2313	Discontinued
0.642	Remote Similarity	NPD6362	Approved
0.642	Remote Similarity	NPD2797	Approved
0.6418	Remote Similarity	NPD7999	Approved
0.6414	Remote Similarity	NPD4107	Approved
0.6407	Remote Similarity	NPD230	Phase 1
0.6407	Remote Similarity	NPD447	Suspended
0.6404	Remote Similarity	NPD6385	Approved
0.6404	Remote Similarity	NPD6386	Approved
0.64	Remote Similarity	NPD7680	Approved
0.6398	Remote Similarity	NPD7177	Discontinued
0.6395	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.6391	Remote Similarity	NPD4308	Phase 3
0.6391	Remote Similarity	NPD1510	Phase 2
0.6389	Remote Similarity	NPD5353	Approved
0.6386	Remote Similarity	NPD6233	Phase 2
0.638	Remote Similarity	NPD5647	Approved
0.6379	Remote Similarity	NPD1511	Approved
0.6378	Remote Similarity	NPD4575	Clinical (unspecified phase)
0.6369	Remote Similarity	NPD1607	Approved
0.6364	Remote Similarity	NPD7095	Approved
0.6359	Remote Similarity	NPD5710	Approved
0.6359	Remote Similarity	NPD5711	Approved
0.6358	Remote Similarity	NPD3887	Approved
0.6358	Remote Similarity	NPD2309	Approved
0.6358	Remote Similarity	NPD1283	Approved
0.635	Remote Similarity	NPD3057	Approved
0.6347	Remote Similarity	NPD4060	Phase 1
0.6347	Remote Similarity	NPD2979	Phase 3
0.6347	Remote Similarity	NPD1240	Approved
0.6341	Remote Similarity	NPD5736	Approved
0.6329	Remote Similarity	NPD9545	Approved
0.6329	Remote Similarity	NPD7930	Approved
0.6324	Remote Similarity	NPD5242	Approved
0.6318	Remote Similarity	NPD7435	Discontinued
0.6313	Remote Similarity	NPD7615	Clinical (unspecified phase)
0.631	Remote Similarity	NPD3751	Discontinued
0.631	Remote Similarity	NPD1899	Clinical (unspecified phase)
0.6307	Remote Similarity	NPD1512	Approved
0.63	Remote Similarity	NPD4482	Phase 3
0.6298	Remote Similarity	NPD7047	Phase 3
0.6298	Remote Similarity	NPD5616	Clinical (unspecified phase)
0.6296	Remote Similarity	NPD5327	Phase 3

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