NPASS Compound

Structure

NPC472775 OpenBabel07101718182D 44 48 0 0 1 0 0 0 0 0999 V2000 -0.4155 -0.7559 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0694 2.9208 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9482 3.2531 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0656 3.6781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2631 0.7659 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7834 0.2051 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7371 0.0587 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0916 6.0119 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3518 -0.2665 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0073 0.4615 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3899 3.4374 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9119 -1.3375 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5593 1.1061 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3924 -0.6827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0925 2.8476 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4569 0.1319 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1619 2.6280 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.0352 4.3200 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7602 -1.8273 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2399 1.8187 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.2656 1.0093 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.9062 1.1006 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.9062 1.1006 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6086 -0.3579 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.6906 1.8919 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.2887 0.9361 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.1388 2.7012 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2631 1.7454 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.7602 0.1319 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.7602 0.1319 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.9119 -0.3579 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.9442 -1.4921 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5407 3.6570 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.0120 4.3932 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7602 -2.8069 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.7784 1.6780 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.8423 1.3893 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.1853 -0.7507 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.5167 5.1294 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.5175 1.3098 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.8174 0.1999 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.6675 1.9651 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.6086 -1.3375 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 14 1 0 0 0 0 2 15 1 0 0 0 0 3 27 1 0 0 0 0 4 27 1 0 0 0 0 6 29 1 0 0 0 0 7 30 1 0 0 0 0 8 39 1 0 0 0 0 9 10 2 0 0 0 0 9 16 1 0 0 0 0 10 40 1 0 0 0 0 11 17 1 0 0 0 0 11 18 1 0 0 0 0 12 19 1 0 0 0 0 13 16 2 0 0 0 0 13 40 1 0 0 0 0 14 32 2 0 0 0 0 14 41 1 0 0 0 0 15 33 2 0 0 0 0 15 42 1 0 0 0 0 16 24 1 0 0 0 0 17 27 1 0 0 0 0 17 28 1 6 0 0 0 18 34 2 0 0 0 0 18 39 1 0 0 0 0 19 35 2 0 0 0 0 19 43 1 0 0 0 0 20 22 1 0 0 0 0 20 23 1 0 0 0 0 20 28 1 6 0 0 0 21 25 1 0 0 0 0 21 26 1 0 0 0 0 21 41 1 1 0 0 0 22 29 1 6 0 0 0 22 36 1 0 0 0 0 23 30 1 0 0 0 0 23 37 2 0 0 0 0 24 29 1 6 0 0 0 24 43 1 0 0 0 0 25 27 1 0 0 0 0 25 42 1 1 0 0 0 26 28 1 1 0 0 0 26 44 1 0 0 0 0 28 5 1 6 0 0 0 29 31 1 1 0 0 0 30 31 1 6 0 0 0 30 38 1 0 0 0 0 31 12 1 1 0 0 0 31 44 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	620.25
Volume:	597.767
LogP:	2.536
LogD:	1.836
LogS:	-4.135
# Rotatable Bonds:	8
TPSA:	185.1
# H-Bond Aceptor:	13
# H-Bond Donor:	2
# Rings:	6
# Heavy Atoms:	13

MedChem Properties

QED Drug-Likeness Score:	0.359
Synthetic Accessibility Score:	6.764
Fsp3:	0.71
Lipinski Rule-of-5:	Rejected
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:	-5.382
MDCK Permeability:	0.000104338
Pgp-inhibitor:	0.998
Pgp-substrate:	0.926
Human Intestinal Absorption (HIA):	0.921
20% Bioavailability (F20%):	0.927
30% Bioavailability (F30%):	0.989

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.226
Plasma Protein Binding (PPB):	60.01%
Volume Distribution (VD):	0.649
Pgp-substrate:	32.18%

ADMET: Metabolism

CYP1A2-inhibitor:	0.006
CYP1A2-substrate:	0.051
CYP2C19-inhibitor:	0.02
CYP2C19-substrate:	0.088
CYP2C9-inhibitor:	0.02
CYP2C9-substrate:	0.009
CYP2D6-inhibitor:	0.083
CYP2D6-substrate:	0.057
CYP3A4-inhibitor:	0.614
CYP3A4-substrate:	0.528

ADMET: Excretion

Clearance (CL):	6.422
Half-life (T1/2):	0.835

ADMET: Toxicity

hERG Blockers:	0.025
Human Hepatotoxicity (H-HT):	0.666
Drug-inuced Liver Injury (DILI):	0.828
AMES Toxicity:	0.042
Rat Oral Acute Toxicity:	0.928
Maximum Recommended Daily Dose:	0.165
Skin Sensitization:	0.089
Carcinogencity:	0.24
Eye Corrosion:	0.007
Eye Irritation:	0.009
Respiratory Toxicity:	0.979

Download Data

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

Natural Product: NPC472775

Natural Product ID:	NPC472775
*Common Name:**	LOQJCDLVFJBVRS-AMIXKSHRSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	LOQJCDLVFJBVRS-AMIXKSHRSA-N
Standard InCHI:	InChI=1S/C31H40O13/c1-14(32)41-21-25(42-15(2)33)27(3,4)17(11-18(34)39-8)28(5)20-22(36)29(6)24(16-9-10-40-13-16)43-19(35)12-31(29,44-26(21)28)30(7,38)23(20)37/h9-10,13,17,20-22,24-26,36,38H,11-12H2,1-8H3/t17-,20-,21-,22-,24-,25+,26-,28-,29-,30+,31+/m0/s1
SMILES:	COC(=O)C[C@@H]1[C@]2(C)[C@@H](O[C@@]34[C@](C(=O)[C@@H]2[C@H](O)[C@@]3(C)[C@@H](OC(=O)C4)c2ccoc2)(C)O)[C@H]([C@H](C1(C)C)OC(=O)C)OC(=O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3582104
PubChem CID:	n.a.
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000264] Organic acids and derivatives [CHEMONTID:0000265] Carboxylic acids and derivatives [CHEMONTID:0002966] Tetracarboxylic acids and derivatives

*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
NPO4584	Cipadessa cinerascens	Species	Meliaceae	Eukaryota	leaves	n.a.	n.a.	PMID[17655260]
NPO4584	Cipadessa cinerascens	Species	Meliaceae	Eukaryota	Leaves	n.a.	n.a.	PMID[19296669]
NPO4584	Cipadessa cinerascens	Species	Meliaceae	Eukaryota	leaves	Longlin County of Guangxi Province, China	2012-JUL	PMID[25970729]
NPO4584	Cipadessa cinerascens	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
EC50	1

Activity Type	# Activity
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT24	Organism	Human immunodeficiency virus 1	Human immunodeficiency virus 1	EC50	>	100000.0	nM	PMID[448509]

☑ 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 NPC472775 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	394
0.1-0.2	1531
0.2-0.3	3460
0.3-0.4	6225
0.4-0.5	10693
0.5-0.6	9758
0.6-0.7	8729
0.7-0.8	1559
0.8-0.85	221
0.85-0.9	104
0.9-0.95	15
0.95-1	8

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC472774
0.9806	High Similarity	NPC472773
0.9742	High Similarity	NPC472771
0.962	High Similarity	NPC476853
0.9618	High Similarity	NPC276551
0.956	High Similarity	NPC471397
0.9557	High Similarity	NPC470875
0.9554	High Similarity	NPC477405
0.9554	High Similarity	NPC469338
0.9554	High Similarity	NPC292389
0.9548	High Similarity	NPC472772
0.9497	High Similarity	NPC173516
0.9494	High Similarity	NPC470940
0.9494	High Similarity	NPC476857
0.9494	High Similarity	NPC476858
0.9494	High Similarity	NPC469849
0.9494	High Similarity	NPC476856
0.949	High Similarity	NPC69028
0.9437	High Similarity	NPC160651
0.9434	High Similarity	NPC23387
0.9427	High Similarity	NPC477402
0.9423	High Similarity	NPC45101
0.9423	High Similarity	NPC167142
0.9375	High Similarity	NPC476850
0.9375	High Similarity	NPC476861
0.9375	High Similarity	NPC472282
0.9375	High Similarity	NPC472651
0.9371	High Similarity	NPC476860
0.9367	High Similarity	NPC329938
0.9367	High Similarity	NPC82851
0.9367	High Similarity	NPC200782
0.9367	High Similarity	NPC263432
0.9363	High Similarity	NPC475967
0.9317	High Similarity	NPC472652
0.9304	High Similarity	NPC25255
0.9295	High Similarity	NPC264943
0.925	High Similarity	NPC271657
0.925	High Similarity	NPC123088
0.9245	High Similarity	NPC193798
0.9241	High Similarity	NPC237155
0.9241	High Similarity	NPC477403
0.9198	High Similarity	NPC271235
0.9198	High Similarity	NPC472766
0.9198	High Similarity	NPC472765
0.9187	High Similarity	NPC51568
0.9187	High Similarity	NPC134254
0.9187	High Similarity	NPC234660
0.9187	High Similarity	NPC39986
0.9187	High Similarity	NPC302369
0.9182	High Similarity	NPC472653
0.9177	High Similarity	NPC249021
0.9172	High Similarity	NPC469336
0.9136	High Similarity	NPC472764
0.9125	High Similarity	NPC18347
0.9125	High Similarity	NPC149896
0.9125	High Similarity	NPC5079
0.9125	High Similarity	NPC470939
0.9114	High Similarity	NPC469485
0.9108	High Similarity	NPC178932
0.9097	High Similarity	NPC69647
0.9097	High Similarity	NPC125182
0.9091	High Similarity	NPC471632
0.9074	High Similarity	NPC97574
0.9074	High Similarity	NPC121995
0.9074	High Similarity	NPC93172
0.9062	High Similarity	NPC335761
0.9062	High Similarity	NPC470789
0.9057	High Similarity	NPC261597
0.9057	High Similarity	NPC472283
0.9057	High Similarity	NPC173544
0.9057	High Similarity	NPC299038
0.9057	High Similarity	NPC36655
0.9051	High Similarity	NPC281258
0.9051	High Similarity	NPC476262
0.9051	High Similarity	NPC44675
0.9051	High Similarity	NPC214541
0.9045	High Similarity	NPC469503
0.9045	High Similarity	NPC476201
0.9024	High Similarity	NPC82602
0.9012	High Similarity	NPC470182
0.9006	High Similarity	NPC96443
0.9006	High Similarity	NPC472767
0.9006	High Similarity	NPC18986
0.9006	High Similarity	NPC290400
0.9006	High Similarity	NPC188649
0.9	High Similarity	NPC475295
0.9	High Similarity	NPC473473
0.8994	High Similarity	NPC126723
0.8994	High Similarity	NPC263265
0.8987	High Similarity	NPC282445
0.8982	High Similarity	NPC478177
0.8976	High Similarity	NPC471437
0.8968	High Similarity	NPC255414
0.8957	High Similarity	NPC472141
0.8957	High Similarity	NPC475779
0.8957	High Similarity	NPC149945
0.8951	High Similarity	NPC472139
0.8951	High Similarity	NPC476197
0.8951	High Similarity	NPC88841
0.8951	High Similarity	NPC288602
0.8938	High Similarity	NPC472778
0.8938	High Similarity	NPC472777
0.8938	High Similarity	NPC286722
0.8938	High Similarity	NPC187149
0.8938	High Similarity	NPC472776
0.8917	High Similarity	NPC469335
0.8917	High Similarity	NPC477404
0.8917	High Similarity	NPC159927
0.8917	High Similarity	NPC196864
0.8917	High Similarity	NPC476122
0.8909	High Similarity	NPC470995
0.8902	High Similarity	NPC476224
0.8902	High Similarity	NPC270312
0.8889	High Similarity	NPC68848
0.8889	High Similarity	NPC207978
0.8889	High Similarity	NPC117986
0.8882	High Similarity	NPC307383
0.8876	High Similarity	NPC470938
0.8875	High Similarity	NPC107646
0.8875	High Similarity	NPC209364
0.8875	High Similarity	NPC60973
0.8862	High Similarity	NPC94763
0.8862	High Similarity	NPC236004
0.8855	High Similarity	NPC160818
0.8855	High Similarity	NPC169299
0.8855	High Similarity	NPC285227
0.8846	High Similarity	NPC470941
0.8839	High Similarity	NPC5676
0.8834	High Similarity	NPC469846
0.8834	High Similarity	NPC419
0.8834	High Similarity	NPC663
0.8834	High Similarity	NPC224394
0.883	High Similarity	NPC105395
0.883	High Similarity	NPC247563
0.883	High Similarity	NPC242068
0.8827	High Similarity	NPC191828
0.8827	High Similarity	NPC305016
0.8827	High Similarity	NPC287559
0.8827	High Similarity	NPC475381
0.882	High Similarity	NPC88007
0.882	High Similarity	NPC194499
0.882	High Similarity	NPC195954
0.8812	High Similarity	NPC469850
0.8812	High Similarity	NPC92979
0.881	High Similarity	NPC262386
0.8805	High Similarity	NPC75906
0.8805	High Similarity	NPC268905
0.8788	High Similarity	NPC473753
0.8788	High Similarity	NPC473766
0.8782	High Similarity	NPC262198
0.878	High Similarity	NPC56358
0.8773	High Similarity	NPC6326
0.8773	High Similarity	NPC211777
0.8765	High Similarity	NPC475226
0.8758	High Similarity	NPC204663
0.875	High Similarity	NPC57998
0.8742	High Similarity	NPC18135
0.8735	High Similarity	NPC296558
0.8727	High Similarity	NPC478178
0.872	High Similarity	NPC285567
0.872	High Similarity	NPC283209
0.872	High Similarity	NPC198047
0.872	High Similarity	NPC472669
0.871	High Similarity	NPC243577
0.8704	High Similarity	NPC197137
0.8704	High Similarity	NPC195131
0.8704	High Similarity	NPC475066
0.8696	High Similarity	NPC35000
0.8696	High Similarity	NPC75310
0.8688	High Similarity	NPC44577
0.8683	High Similarity	NPC472659
0.8679	High Similarity	NPC46551
0.8679	High Similarity	NPC156189
0.8659	High Similarity	NPC471166
0.8659	High Similarity	NPC471167
0.8659	High Similarity	NPC472668
0.8659	High Similarity	NPC470792
0.8654	High Similarity	NPC476944
0.865	High Similarity	NPC474611
0.865	High Similarity	NPC472671
0.865	High Similarity	NPC262872
0.8647	High Similarity	NPC472665
0.8645	High Similarity	NPC121158
0.8642	High Similarity	NPC41880
0.8639	High Similarity	NPC469576
0.8634	High Similarity	NPC302054
0.8634	High Similarity	NPC30222
0.8634	High Similarity	NPC253201
0.8616	High Similarity	NPC472654
0.8616	High Similarity	NPC195325
0.8606	High Similarity	NPC471168
0.8606	High Similarity	NPC165218
0.859	High Similarity	NPC476946
0.8588	High Similarity	NPC469633
0.858	High Similarity	NPC141538
0.858	High Similarity	NPC296807
0.858	High Similarity	NPC469848
0.858	High Similarity	NPC155939
0.8571	High Similarity	NPC33938
0.8571	High Similarity	NPC147168

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 NPC472775 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	336
0.1-0.2	1091
0.2-0.3	2317
0.3-0.4	2728
0.4-0.5	1728
0.5-0.6	706
0.6-0.7	222
0.7-0.8	22
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
0.8772	High Similarity	NPD8434	Phase 2
0.8354	Intermediate Similarity	NPD5760	Phase 2
0.8354	Intermediate Similarity	NPD5761	Phase 2
0.8047	Intermediate Similarity	NPD5537	Clinical (unspecified phase)
0.7753	Intermediate Similarity	NPD6764	Approved
0.7753	Intermediate Similarity	NPD6765	Approved
0.7706	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7674	Intermediate Similarity	NPD7075	Discontinued
0.7582	Intermediate Similarity	NPD6784	Approved
0.7582	Intermediate Similarity	NPD6785	Approved
0.7582	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7556	Intermediate Similarity	NPD6559	Discontinued
0.7529	Intermediate Similarity	NPD6599	Discontinued
0.7525	Intermediate Similarity	NPD8404	Phase 2
0.75	Intermediate Similarity	NPD7819	Suspended
0.7473	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7442	Intermediate Similarity	NPD6801	Discontinued
0.741	Intermediate Similarity	NPD4628	Phase 3
0.7386	Intermediate Similarity	NPD5494	Approved
0.7356	Intermediate Similarity	NPD3817	Phase 2
0.7356	Intermediate Similarity	NPD5402	Approved
0.7345	Intermediate Similarity	NPD1247	Approved
0.7293	Intermediate Similarity	NPD5844	Phase 1
0.7283	Intermediate Similarity	NPD7411	Suspended
0.7278	Intermediate Similarity	NPD6799	Approved
0.7258	Intermediate Similarity	NPD8150	Discontinued
0.7257	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7238	Intermediate Similarity	NPD3818	Discontinued
0.7232	Intermediate Similarity	NPD919	Approved
0.7228	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7225	Intermediate Similarity	NPD4380	Phase 2
0.7222	Intermediate Similarity	NPD6166	Phase 2
0.7222	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7216	Intermediate Similarity	NPD3882	Suspended
0.7216	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7213	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.72	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7198	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7182	Intermediate Similarity	NPD7473	Discontinued
0.7175	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7175	Intermediate Similarity	NPD3749	Approved
0.7168	Intermediate Similarity	NPD3226	Approved
0.7151	Intermediate Similarity	NPD5403	Approved
0.7151	Intermediate Similarity	NPD8407	Phase 2
0.7151	Intermediate Similarity	NPD920	Approved
0.7143	Intermediate Similarity	NPD1934	Approved
0.7143	Intermediate Similarity	NPD3751	Discontinued
0.7135	Intermediate Similarity	NPD5401	Approved
0.7126	Intermediate Similarity	NPD1471	Phase 3
0.7111	Intermediate Similarity	NPD3787	Discontinued
0.7097	Intermediate Similarity	NPD8312	Approved
0.7097	Intermediate Similarity	NPD8313	Approved
0.7092	Intermediate Similarity	NPD7435	Discontinued
0.7081	Intermediate Similarity	NPD7251	Discontinued
0.7081	Intermediate Similarity	NPD8368	Discontinued
0.7065	Intermediate Similarity	NPD7074	Phase 3
0.7056	Intermediate Similarity	NPD8127	Discontinued
0.7043	Intermediate Similarity	NPD7808	Phase 3
0.7041	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7035	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7035	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7035	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7033	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7027	Intermediate Similarity	NPD6797	Phase 2
0.7024	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7017	Intermediate Similarity	NPD6232	Discontinued
0.7011	Intermediate Similarity	NPD7054	Approved
0.7006	Intermediate Similarity	NPD2801	Approved
0.7006	Intermediate Similarity	NPD2799	Discontinued
0.7	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.6978	Remote Similarity	NPD3926	Phase 2
0.6973	Remote Similarity	NPD7472	Approved
0.6957	Remote Similarity	NPD7799	Discontinued
0.6949	Remote Similarity	NPD37	Approved
0.6939	Remote Similarity	NPD6782	Approved
0.6939	Remote Similarity	NPD6780	Approved
0.6939	Remote Similarity	NPD6781	Approved
0.6939	Remote Similarity	NPD6777	Approved
0.6939	Remote Similarity	NPD6779	Approved
0.6939	Remote Similarity	NPD6778	Approved
0.6939	Remote Similarity	NPD6776	Approved
0.6936	Remote Similarity	NPD2532	Approved
0.6936	Remote Similarity	NPD2533	Approved
0.6936	Remote Similarity	NPD2534	Approved
0.6927	Remote Similarity	NPD4966	Approved
0.6927	Remote Similarity	NPD4965	Approved
0.6927	Remote Similarity	NPD4967	Phase 2
0.6923	Remote Similarity	NPD2346	Discontinued
0.6919	Remote Similarity	NPD7236	Approved
0.6919	Remote Similarity	NPD643	Clinical (unspecified phase)
0.6897	Remote Similarity	NPD6273	Approved
0.6885	Remote Similarity	NPD7184	Clinical (unspecified phase)
0.6882	Remote Similarity	NPD1549	Phase 2
0.6881	Remote Similarity	NPD7875	Clinical (unspecified phase)
0.6881	Remote Similarity	NPD7874	Approved
0.6875	Remote Similarity	NPD7907	Approved
0.6868	Remote Similarity	NPD6959	Discontinued
0.6868	Remote Similarity	NPD7199	Phase 2
0.6865	Remote Similarity	NPD7893	Clinical (unspecified phase)
0.6865	Remote Similarity	NPD7228	Approved
0.6864	Remote Similarity	NPD2796	Approved
0.6864	Remote Similarity	NPD6099	Approved
0.6864	Remote Similarity	NPD6100	Approved
0.686	Remote Similarity	NPD4111	Phase 1
0.686	Remote Similarity	NPD4665	Approved
0.686	Remote Similarity	NPD6190	Approved
0.6851	Remote Similarity	NPD6234	Discontinued
0.6834	Remote Similarity	NPD7696	Phase 3
0.6834	Remote Similarity	NPD7697	Approved
0.6834	Remote Similarity	NPD7698	Approved
0.6826	Remote Similarity	NPD6355	Discontinued
0.6824	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6824	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.6823	Remote Similarity	NPD8397	Clinical (unspecified phase)
0.6823	Remote Similarity	NPD8435	Approved
0.6823	Remote Similarity	NPD8360	Approved
0.6823	Remote Similarity	NPD8361	Approved
0.6818	Remote Similarity	NPD7239	Suspended
0.6816	Remote Similarity	NPD1465	Phase 2
0.6809	Remote Similarity	NPD7685	Pre-registration
0.68	Remote Similarity	NPD7870	Phase 2
0.68	Remote Similarity	NPD7871	Phase 2
0.68	Remote Similarity	NPD1512	Approved
0.6782	Remote Similarity	NPD7701	Phase 2
0.678	Remote Similarity	NPD7458	Discontinued
0.678	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6766	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.6765	Remote Similarity	NPD1551	Phase 2
0.6765	Remote Similarity	NPD7801	Approved
0.6761	Remote Similarity	NPD6980	Clinical (unspecified phase)
0.675	Remote Similarity	NPD7497	Discontinued
0.6744	Remote Similarity	NPD1243	Approved
0.6744	Remote Similarity	NPD2800	Approved
0.6743	Remote Similarity	NPD7410	Clinical (unspecified phase)
0.674	Remote Similarity	NPD7768	Phase 2
0.6738	Remote Similarity	NPD8470	Clinical (unspecified phase)
0.673	Remote Similarity	NPD5619	Clinical (unspecified phase)
0.6725	Remote Similarity	NPD5762	Approved
0.6725	Remote Similarity	NPD5763	Approved
0.672	Remote Similarity	NPD7240	Approved
0.6716	Remote Similarity	NPD8319	Approved
0.6716	Remote Similarity	NPD8320	Phase 1
0.6706	Remote Similarity	NPD7033	Discontinued
0.6705	Remote Similarity	NPD3750	Approved
0.6686	Remote Similarity	NPD970	Clinical (unspecified phase)
0.6686	Remote Similarity	NPD1511	Approved
0.6684	Remote Similarity	NPD6535	Approved
0.6684	Remote Similarity	NPD6534	Approved
0.6667	Remote Similarity	NPD2935	Discontinued
0.6667	Remote Similarity	NPD7699	Phase 2
0.6667	Remote Similarity	NPD2403	Approved
0.6667	Remote Similarity	NPD7700	Phase 2
0.6649	Remote Similarity	NPD7229	Phase 3
0.6647	Remote Similarity	NPD3268	Approved
0.6647	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6647	Remote Similarity	NPD2313	Discontinued
0.6633	Remote Similarity	NPD8285	Discontinued
0.663	Remote Similarity	NPD8455	Phase 2
0.6628	Remote Similarity	NPD2344	Approved
0.6627	Remote Similarity	NPD6832	Phase 2
0.6617	Remote Similarity	NPD3057	Approved
0.6617	Remote Similarity	NPD6823	Phase 2
0.6616	Remote Similarity	NPD8485	Approved
0.6616	Remote Similarity	NPD8090	Clinical (unspecified phase)
0.6609	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.6608	Remote Similarity	NPD1510	Phase 2
0.6608	Remote Similarity	NPD3748	Approved
0.6607	Remote Similarity	NPD6233	Phase 2
0.6602	Remote Similarity	NPD7783	Phase 2
0.6602	Remote Similarity	NPD7782	Clinical (unspecified phase)
0.66	Remote Similarity	NPD4107	Approved
0.6587	Remote Similarity	NPD7095	Approved
0.6585	Remote Similarity	NPD8151	Discontinued
0.6559	Remote Similarity	NPD5711	Approved
0.6559	Remote Similarity	NPD6808	Phase 2
0.6559	Remote Similarity	NPD5710	Approved
0.6557	Remote Similarity	NPD8155	Clinical (unspecified phase)
0.655	Remote Similarity	NPD7097	Phase 1
0.6548	Remote Similarity	NPD6798	Discontinued
0.6546	Remote Similarity	NPD8424	Clinical (unspecified phase)
0.6535	Remote Similarity	NPD2972	Approved
0.6535	Remote Similarity	NPD3533	Approved
0.6529	Remote Similarity	NPD447	Suspended
0.6517	Remote Similarity	NPD7314	Clinical (unspecified phase)
0.6517	Remote Similarity	NPD8486	Clinical (unspecified phase)
0.6517	Remote Similarity	NPD7501	Clinical (unspecified phase)
0.6514	Remote Similarity	NPD4109	Clinical (unspecified phase)
0.6514	Remote Similarity	NPD4110	Phase 3
0.6508	Remote Similarity	NPD2163	Approved
0.6497	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6494	Remote Similarity	NPD2424	Discontinued
0.6492	Remote Similarity	NPD5953	Discontinued
0.6491	Remote Similarity	NPD1607	Approved
0.6489	Remote Similarity	NPD4575	Clinical (unspecified phase)
0.6485	Remote Similarity	NPD4482	Phase 3
0.6477	Remote Similarity	NPD2309	Approved
0.6477	Remote Similarity	NPD2354	Approved
0.6477	Remote Similarity	NPD3887	Approved
0.6474	Remote Similarity	NPD7286	Phase 2

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