NPASS Compound

Structure

NPC290400 OpenBabel07101719252D 36 41 0 0 1 0 0 0 0 0999 V2000 -1.6908 1.9524 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0243 -1.5951 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5124 -2.4405 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -2.9286 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5362 -1.4643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 0.9762 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6908 -3.9048 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2734 -0.5791 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8454 -3.4167 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9266 -1.3046 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6908 -0.9762 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6908 -1.9524 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4837 -1.9470 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6908 0.9762 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3816 -0.9762 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8454 -2.4405 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.6908 -1.9524 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.5362 -3.4167 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8454 -0.4881 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.0000 -1.9524 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.5362 -0.4881 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8454 0.4881 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.6908 0.9762 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5362 -2.4405 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8454 -2.4405 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.6908 -0.9762 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.0000 -0.9762 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8454 -0.4881 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.5362 0.4881 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8454 -3.4167 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.3816 -3.9048 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.6908 1.9524 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.4385 -2.1500 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8454 0.4881 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5362 0.4881 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 24 1 0 0 0 0 3 24 1 0 0 0 0 5 26 1 0 0 0 0 6 27 1 0 0 0 0 7 9 2 0 0 0 0 7 18 1 0 0 0 0 8 10 2 0 0 0 0 8 15 1 0 0 0 0 9 25 1 0 0 0 0 10 33 1 0 0 0 0 11 17 1 0 0 0 0 11 19 1 0 0 0 0 12 16 1 0 0 0 0 12 26 1 0 0 0 0 13 15 2 0 0 0 0 13 33 1 0 0 0 0 14 29 2 0 0 0 0 14 34 1 0 0 0 0 15 21 1 0 0 0 0 16 20 1 0 0 0 0 16 30 1 6 0 0 0 17 24 1 0 0 0 0 17 25 1 6 0 0 0 18 24 1 0 0 0 0 18 31 2 0 0 0 0 19 27 1 1 0 0 0 19 34 1 0 0 0 0 20 25 1 6 0 0 0 20 27 1 0 0 0 0 21 26 1 1 0 0 0 21 35 1 0 0 0 0 22 23 1 0 0 0 0 22 28 1 1 0 0 0 22 36 1 0 0 0 0 23 32 2 0 0 0 0 23 35 1 0 0 0 0 25 4 1 6 0 0 0 26 28 1 1 0 0 0 27 28 1 1 0 0 0 28 36 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	498.23
Volume:	496.008
LogP:	3.327
LogD:	2.748
LogS:	-4.596
# Rotatable Bonds:	3
TPSA:	115.57
# H-Bond Aceptor:	8
# H-Bond Donor:	1
# Rings:	6
# Heavy Atoms:	8

MedChem Properties

QED Drug-Likeness Score:	0.486
Synthetic Accessibility Score:	5.777
Fsp3:	0.679
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:	-5.387
MDCK Permeability:	1.4056824511499144e-05
Pgp-inhibitor:	0.998
Pgp-substrate:	0.259
Human Intestinal Absorption (HIA):	0.015
20% Bioavailability (F20%):	0.971
30% Bioavailability (F30%):	0.968

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.854
Plasma Protein Binding (PPB):	81.92952728271484%
Volume Distribution (VD):	1.947
Pgp-substrate:	18.585052490234375%

ADMET: Metabolism

CYP1A2-inhibitor:	0.011
CYP1A2-substrate:	0.119
CYP2C19-inhibitor:	0.05
CYP2C19-substrate:	0.388
CYP2C9-inhibitor:	0.331
CYP2C9-substrate:	0.024
CYP2D6-inhibitor:	0.034
CYP2D6-substrate:	0.04
CYP3A4-inhibitor:	0.863
CYP3A4-substrate:	0.658

ADMET: Excretion

Clearance (CL):	5.719
Half-life (T1/2):	0.274

ADMET: Toxicity

hERG Blockers:	0.063
Human Hepatotoxicity (H-HT):	0.443
Drug-inuced Liver Injury (DILI):	0.24
AMES Toxicity:	0.058
Rat Oral Acute Toxicity:	0.868
Maximum Recommended Daily Dose:	0.923
Skin Sensitization:	0.195
Carcinogencity:	0.36
Eye Corrosion:	0.03
Eye Irritation:	0.025
Respiratory Toxicity:	0.975

Download Data

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

Natural Product: NPC290400

Natural Product ID:	NPC290400
*Common Name:**	CJCDIECVGAPJFT-ZINBXAAWSA-N
IUPAC Name:	n.a.
Synonyms:	11Beta-Hydroxygedunin
Standard InCHIKey:	CJCDIECVGAPJFT-ZINBXAAWSA-N
Standard InCHI:	InChI=1S/C28H34O8/c1-14(29)34-19-11-17-24(2,3)18(31)7-9-25(17,4)20-16(30)12-26(5)21(15-8-10-33-13-15)35-23(32)22-28(26,36-22)27(19,20)6/h7-10,13,16-17,19-22,30H,11-12H2,1-6H3/t16-,17-,19+,20+,21-,22+,25-,26-,27+,28+/m0/s1
SMILES:	CC(=O)O[C@@H]1C[C@H]2C(C)(C)C(=O)C=C[C@]2(C)[C@H]2[C@H](C[C@@]3(C)[C@H](c4ccoc4)OC(=O)[C@@H]4[C@@]3([C@]12C)O4)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL462806
PubChem CID:	16086555
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
NPO29947	Cedrela sinensis	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16989525]
NPO29947	Cedrela sinensis	Species	Meliaceae	Eukaryota	n.a.	cortex	n.a.	PMID[16989525]

☑ 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

Activity Type	# Activity
Cell Line	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT168	Cell Line	P388	Mus musculus	IC50	=	5.4	ug.mL-1	PMID[530822]

☑ 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 NPC290400 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	359
0.1-0.2	1430
0.2-0.3	3185
0.3-0.4	5542
0.4-0.5	9918
0.5-0.6	10474
0.6-0.7	9239
0.7-0.8	2102
0.8-0.85	268
0.85-0.9	108
0.9-0.95	52
0.95-1	20

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC96443
0.9675	High Similarity	NPC234660
0.9675	High Similarity	NPC51568
0.961	High Similarity	NPC117986
0.961	High Similarity	NPC5079
0.9487	High Similarity	NPC476857
0.9487	High Similarity	NPC476858
0.9487	High Similarity	NPC476856
0.9481	High Similarity	NPC475295
0.9481	High Similarity	NPC473473
0.9423	High Similarity	NPC39986
0.9423	High Similarity	NPC302369
0.9423	High Similarity	NPC134254
0.9419	High Similarity	NPC335761
0.9416	High Similarity	NPC286722
0.9367	High Similarity	NPC476861
0.9367	High Similarity	NPC476853
0.9367	High Similarity	NPC476850
0.9351	High Similarity	NPC209364
0.9308	High Similarity	NPC471397
0.9304	High Similarity	NPC23387
0.9295	High Similarity	NPC25255
0.9295	High Similarity	NPC472653
0.9245	High Similarity	NPC173516
0.9245	High Similarity	NPC472282
0.9241	High Similarity	NPC123088
0.9241	High Similarity	NPC276551
0.9241	High Similarity	NPC476860
0.9236	High Similarity	NPC69028
0.9236	High Similarity	NPC193798
0.9226	High Similarity	NPC107646
0.9187	High Similarity	NPC271235
0.9182	High Similarity	NPC470875
0.9177	High Similarity	NPC292389
0.9177	High Similarity	NPC469338
0.9177	High Similarity	NPC477405
0.9172	High Similarity	NPC475381
0.9125	High Similarity	NPC472651
0.9119	High Similarity	NPC271657
0.9119	High Similarity	NPC469849
0.9119	High Similarity	NPC470940
0.9114	High Similarity	NPC82851
0.9114	High Similarity	NPC470939
0.9114	High Similarity	NPC149896
0.9108	High Similarity	NPC477403
0.9103	High Similarity	NPC60973
0.9103	High Similarity	NPC126723
0.9068	High Similarity	NPC472652
0.9068	High Similarity	NPC160651
0.9051	High Similarity	NPC477402
0.9045	High Similarity	NPC249021
0.9045	High Similarity	NPC472283
0.9038	High Similarity	NPC469336
0.9032	High Similarity	NPC469503
0.9006	High Similarity	NPC472774
0.9006	High Similarity	NPC473753
0.9006	High Similarity	NPC473766
0.9006	High Similarity	NPC472775
0.8994	High Similarity	NPC263432
0.8994	High Similarity	NPC18347
0.8994	High Similarity	NPC200782
0.8987	High Similarity	NPC237155
0.8974	High Similarity	NPC57998
0.8974	High Similarity	NPC178932
0.8938	High Similarity	NPC469846
0.8931	High Similarity	NPC305016
0.8924	High Similarity	NPC45101
0.8924	High Similarity	NPC187149
0.8917	High Similarity	NPC44675
0.8917	High Similarity	NPC214541
0.8917	High Similarity	NPC469850
0.8909	High Similarity	NPC262386
0.8875	High Similarity	NPC472771
0.8875	High Similarity	NPC329938
0.8868	High Similarity	NPC307383
0.8868	High Similarity	NPC475967
0.8861	High Similarity	NPC263265
0.8854	High Similarity	NPC282445
0.8841	High Similarity	NPC160818
0.8841	High Similarity	NPC169299
0.8834	High Similarity	NPC242334
0.8827	High Similarity	NPC475779
0.8827	High Similarity	NPC478178
0.882	High Similarity	NPC472773
0.882	High Similarity	NPC472139
0.8805	High Similarity	NPC261597
0.8805	High Similarity	NPC299038
0.8805	High Similarity	NPC36655
0.8805	High Similarity	NPC472772
0.8797	High Similarity	NPC35000
0.8797	High Similarity	NPC264943
0.8797	High Similarity	NPC281258
0.8797	High Similarity	NPC476262
0.879	High Similarity	NPC476201
0.8782	High Similarity	NPC469335
0.8782	High Similarity	NPC159927
0.8782	High Similarity	NPC476122
0.878	High Similarity	NPC470995
0.878	High Similarity	NPC302392
0.878	High Similarity	NPC82602
0.8765	High Similarity	NPC470182
0.8758	High Similarity	NPC207978
0.8758	High Similarity	NPC211777
0.8742	High Similarity	NPC469485
0.8734	High Similarity	NPC30222
0.8726	High Similarity	NPC18135
0.8712	High Similarity	NPC93172
0.8712	High Similarity	NPC97574
0.8704	High Similarity	NPC476197
0.8704	High Similarity	NPC198047
0.8688	High Similarity	NPC173544
0.8671	High Similarity	NPC75906
0.8671	High Similarity	NPC44577
0.8662	High Similarity	NPC46551
0.8662	High Similarity	NPC477404
0.8662	High Similarity	NPC196864
0.8659	High Similarity	NPC478179
0.8642	High Similarity	NPC5741
0.8636	High Similarity	NPC86935
0.8634	High Similarity	NPC262872
0.8634	High Similarity	NPC473368
0.8623	High Similarity	NPC236004
0.8614	High Similarity	NPC159232
0.8599	High Similarity	NPC69647
0.8599	High Similarity	NPC125182
0.8596	High Similarity	NPC247563
0.8596	High Similarity	NPC242068
0.859	High Similarity	NPC255414
0.859	High Similarity	NPC221809
0.8589	High Similarity	NPC419
0.8589	High Similarity	NPC224394
0.8589	High Similarity	NPC663
0.858	High Similarity	NPC191828
0.858	High Similarity	NPC470789
0.8571	High Similarity	NPC472776
0.8571	High Similarity	NPC472777
0.8571	High Similarity	NPC472778
0.8571	High Similarity	NPC167142
0.8553	High Similarity	NPC268905
0.8545	High Similarity	NPC100333
0.8537	High Similarity	NPC146991
0.8537	High Similarity	NPC259943
0.8528	High Similarity	NPC197596
0.8528	High Similarity	NPC188649
0.8526	High Similarity	NPC262198
0.8521	High Similarity	NPC478177
0.8519	High Similarity	NPC474611
0.8516	High Similarity	NPC476944
0.8512	High Similarity	NPC94763
0.8506	High Similarity	NPC121158
0.8488	Intermediate Similarity	NPC105395
0.8485	Intermediate Similarity	NPC472141
0.8481	Intermediate Similarity	NPC472654
0.8481	Intermediate Similarity	NPC195325
0.8476	Intermediate Similarity	NPC165218
0.8476	Intermediate Similarity	NPC88841
0.8476	Intermediate Similarity	NPC288602
0.8471	Intermediate Similarity	NPC250228
0.8471	Intermediate Similarity	NPC470941
0.8462	Intermediate Similarity	NPC41182
0.8457	Intermediate Similarity	NPC195954
0.8452	Intermediate Similarity	NPC243577
0.8447	Intermediate Similarity	NPC471175
0.8443	Intermediate Similarity	NPC472650
0.8421	Intermediate Similarity	NPC470938
0.8415	Intermediate Similarity	NPC472668
0.8412	Intermediate Similarity	NPC470181
0.8408	Intermediate Similarity	NPC346
0.8405	Intermediate Similarity	NPC474932
0.8405	Intermediate Similarity	NPC475226
0.8402	Intermediate Similarity	NPC471437
0.8397	Intermediate Similarity	NPC251865
0.8397	Intermediate Similarity	NPC137295
0.8395	Intermediate Similarity	NPC471169
0.8395	Intermediate Similarity	NPC175964
0.8393	Intermediate Similarity	NPC285227
0.8385	Intermediate Similarity	NPC114880
0.8383	Intermediate Similarity	NPC327922
0.8383	Intermediate Similarity	NPC296558
0.8377	Intermediate Similarity	NPC67003
0.8373	Intermediate Similarity	NPC214600
0.8373	Intermediate Similarity	NPC121995
0.8364	Intermediate Similarity	NPC472669
0.8354	Intermediate Similarity	NPC471174
0.8344	Intermediate Similarity	NPC88007
0.8344	Intermediate Similarity	NPC470118
0.8344	Intermediate Similarity	NPC194499
0.8344	Intermediate Similarity	NPC5676
0.8343	Intermediate Similarity	NPC469848
0.8333	Intermediate Similarity	NPC141538
0.8333	Intermediate Similarity	NPC92979
0.8333	Intermediate Similarity	NPC75310
0.8333	Intermediate Similarity	NPC155939
0.8333	Intermediate Similarity	NPC296807
0.8333	Intermediate Similarity	NPC472659
0.8323	Intermediate Similarity	NPC246164
0.8323	Intermediate Similarity	NPC476939
0.8323	Intermediate Similarity	NPC84063
0.8323	Intermediate Similarity	NPC472764
0.8323	Intermediate Similarity	NPC476940

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 NPC290400 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	307
0.1-0.2	1028
0.2-0.3	2169
0.3-0.4	2632
0.4-0.5	1827
0.5-0.6	875
0.6-0.7	271
0.7-0.8	39
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
0.8324	Intermediate Similarity	NPD8434	Phase 2
0.8221	Intermediate Similarity	NPD5760	Phase 2
0.8221	Intermediate Similarity	NPD5761	Phase 2
0.7917	Intermediate Similarity	NPD5537	Clinical (unspecified phase)
0.7727	Intermediate Similarity	NPD6764	Approved
0.7727	Intermediate Similarity	NPD6765	Approved
0.7679	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7647	Intermediate Similarity	NPD7075	Discontinued
0.7556	Intermediate Similarity	NPD6784	Approved
0.7556	Intermediate Similarity	NPD6785	Approved
0.7541	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD6599	Discontinued
0.7471	Intermediate Similarity	NPD7819	Suspended
0.7427	Intermediate Similarity	NPD5402	Approved
0.7412	Intermediate Similarity	NPD6801	Discontinued
0.7401	Intermediate Similarity	NPD3751	Discontinued
0.7378	Intermediate Similarity	NPD4628	Phase 3
0.7322	Intermediate Similarity	NPD8150	Discontinued
0.7289	Intermediate Similarity	NPD7236	Approved
0.7273	Intermediate Similarity	NPD3787	Discontinued
0.7268	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7263	Intermediate Similarity	NPD5844	Phase 1
0.7263	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7257	Intermediate Similarity	NPD5494	Approved
0.7246	Intermediate Similarity	NPD6799	Approved
0.7238	Intermediate Similarity	NPD6559	Discontinued
0.7236	Intermediate Similarity	NPD8404	Phase 2
0.7225	Intermediate Similarity	NPD3817	Phase 2
0.7219	Intermediate Similarity	NPD5403	Approved
0.7207	Intermediate Similarity	NPD7799	Discontinued
0.7202	Intermediate Similarity	NPD5401	Approved
0.7202	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7198	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7193	Intermediate Similarity	NPD4380	Phase 2
0.7176	Intermediate Similarity	NPD7239	Suspended
0.7158	Intermediate Similarity	NPD8313	Approved
0.7158	Intermediate Similarity	NPD8312	Approved
0.7151	Intermediate Similarity	NPD7411	Suspended
0.715	Intermediate Similarity	NPD7435	Discontinued
0.7143	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7126	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7119	Intermediate Similarity	NPD8127	Discontinued
0.7095	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7095	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7095	Intermediate Similarity	NPD6166	Phase 2
0.7086	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7066	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD6273	Approved
0.7056	Intermediate Similarity	NPD7473	Discontinued
0.7049	Intermediate Similarity	NPD8368	Discontinued
0.7049	Intermediate Similarity	NPD7251	Discontinued
0.7045	Intermediate Similarity	NPD3749	Approved
0.7035	Intermediate Similarity	NPD3226	Approved
0.7027	Intermediate Similarity	NPD8407	Phase 2
0.7011	Intermediate Similarity	NPD7808	Phase 3
0.7006	Intermediate Similarity	NPD919	Approved
0.7	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.6995	Remote Similarity	NPD7993	Clinical (unspecified phase)
0.6995	Remote Similarity	NPD6797	Phase 2
0.6989	Remote Similarity	NPD3882	Suspended
0.6988	Remote Similarity	NPD2346	Discontinued
0.6971	Remote Similarity	NPD2393	Clinical (unspecified phase)
0.6957	Remote Similarity	NPD7685	Pre-registration
0.694	Remote Similarity	NPD7074	Phase 3
0.6936	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6936	Remote Similarity	NPD7458	Discontinued
0.6935	Remote Similarity	NPD7874	Approved
0.6935	Remote Similarity	NPD7875	Clinical (unspecified phase)
0.6927	Remote Similarity	NPD7907	Approved
0.6927	Remote Similarity	NPD1247	Approved
0.6927	Remote Similarity	NPD6959	Discontinued
0.6923	Remote Similarity	NPD3818	Discontinued
0.6919	Remote Similarity	NPD920	Approved
0.6914	Remote Similarity	NPD1934	Approved
0.6912	Remote Similarity	NPD4111	Phase 1
0.6907	Remote Similarity	NPD6781	Approved
0.6907	Remote Similarity	NPD6778	Approved
0.6907	Remote Similarity	NPD6782	Approved
0.6907	Remote Similarity	NPD6780	Approved
0.6907	Remote Similarity	NPD6777	Approved
0.6907	Remote Similarity	NPD6779	Approved
0.6907	Remote Similarity	NPD6776	Approved
0.6906	Remote Similarity	NPD7852	Clinical (unspecified phase)
0.6905	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.689	Remote Similarity	NPD6355	Discontinued
0.6889	Remote Similarity	NPD6232	Discontinued
0.6888	Remote Similarity	NPD7697	Approved
0.6888	Remote Similarity	NPD7696	Phase 3
0.6888	Remote Similarity	NPD7698	Approved
0.6886	Remote Similarity	NPD2343	Clinical (unspecified phase)
0.6886	Remote Similarity	NPD1471	Phase 3
0.6885	Remote Similarity	NPD7054	Approved
0.6878	Remote Similarity	NPD8397	Clinical (unspecified phase)
0.6878	Remote Similarity	NPD8435	Approved
0.6867	Remote Similarity	NPD2799	Discontinued
0.6864	Remote Similarity	NPD3750	Approved
0.686	Remote Similarity	NPD5619	Clinical (unspecified phase)
0.6853	Remote Similarity	NPD7870	Phase 2
0.6853	Remote Similarity	NPD7871	Phase 2
0.6848	Remote Similarity	NPD7472	Approved
0.6845	Remote Similarity	NPD1549	Phase 2
0.6829	Remote Similarity	NPD4665	Approved
0.6826	Remote Similarity	NPD6100	Approved
0.6826	Remote Similarity	NPD6099	Approved
0.6826	Remote Similarity	NPD2796	Approved
0.6821	Remote Similarity	NPD4107	Approved
0.6802	Remote Similarity	NPD7410	Clinical (unspecified phase)
0.6802	Remote Similarity	NPD2532	Approved
0.6802	Remote Similarity	NPD2534	Approved
0.6802	Remote Similarity	NPD642	Clinical (unspecified phase)
0.6802	Remote Similarity	NPD2533	Approved
0.6798	Remote Similarity	NPD7058	Phase 2
0.6798	Remote Similarity	NPD7057	Phase 3
0.6798	Remote Similarity	NPD7768	Phase 2
0.6789	Remote Similarity	NPD8360	Approved
0.6789	Remote Similarity	NPD8361	Approved
0.6786	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6786	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.6786	Remote Similarity	NPD5762	Approved
0.6786	Remote Similarity	NPD5763	Approved
0.678	Remote Similarity	NPD2801	Approved
0.6772	Remote Similarity	NPD8424	Clinical (unspecified phase)
0.6769	Remote Similarity	NPD8285	Discontinued
0.6768	Remote Similarity	NPD8319	Approved
0.6768	Remote Similarity	NPD8320	Phase 1
0.6766	Remote Similarity	NPD7033	Discontinued
0.6766	Remote Similarity	NPD3748	Approved
0.6751	Remote Similarity	NPD3057	Approved
0.675	Remote Similarity	NPD7701	Phase 2
0.6733	Remote Similarity	NPD7801	Approved
0.6726	Remote Similarity	NPD1551	Phase 2
0.6726	Remote Similarity	NPD2935	Discontinued
0.6725	Remote Similarity	NPD6190	Approved
0.6723	Remote Similarity	NPD37	Approved
0.6707	Remote Similarity	NPD2313	Discontinued
0.6707	Remote Similarity	NPD7097	Phase 1
0.6706	Remote Similarity	NPD2800	Approved
0.6704	Remote Similarity	NPD4965	Approved
0.6704	Remote Similarity	NPD4967	Phase 2
0.6704	Remote Similarity	NPD4966	Approved
0.6703	Remote Similarity	NPD8470	Clinical (unspecified phase)
0.6701	Remote Similarity	NPD4482	Phase 3
0.6687	Remote Similarity	NPD6832	Phase 2
0.6686	Remote Similarity	NPD643	Clinical (unspecified phase)
0.6685	Remote Similarity	NPD1465	Phase 2
0.6685	Remote Similarity	NPD8455	Phase 2
0.6667	Remote Similarity	NPD3533	Approved
0.6667	Remote Similarity	NPD8485	Approved
0.6667	Remote Similarity	NPD3926	Phase 2
0.6667	Remote Similarity	NPD8090	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6233	Phase 2
0.6667	Remote Similarity	NPD7184	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD2972	Approved
0.665	Remote Similarity	NPD7783	Phase 2
0.665	Remote Similarity	NPD7782	Clinical (unspecified phase)
0.6649	Remote Similarity	NPD6534	Approved
0.6649	Remote Similarity	NPD7228	Approved
0.6649	Remote Similarity	NPD6535	Approved
0.6647	Remote Similarity	NPD970	Clinical (unspecified phase)
0.6646	Remote Similarity	NPD7095	Approved
0.6633	Remote Similarity	NPD7497	Discontinued
0.6633	Remote Similarity	NPD7700	Phase 2
0.6633	Remote Similarity	NPD7699	Phase 2
0.6628	Remote Similarity	NPD3887	Approved
0.6627	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.6606	Remote Similarity	NPD6798	Discontinued
0.6606	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6603	Remote Similarity	NPD8155	Clinical (unspecified phase)
0.6583	Remote Similarity	NPD6823	Phase 2
0.6571	Remote Similarity	NPD7314	Clinical (unspecified phase)
0.6571	Remote Similarity	NPD1512	Approved
0.657	Remote Similarity	NPD7003	Approved
0.6568	Remote Similarity	NPD1510	Phase 2
0.6566	Remote Similarity	NPD8486	Clinical (unspecified phase)
0.6559	Remote Similarity	NPD7893	Clinical (unspecified phase)
0.6557	Remote Similarity	NPD7199	Phase 2
0.6541	Remote Similarity	NPD7784	Clinical (unspecified phase)
0.6538	Remote Similarity	NPD6234	Discontinued
0.6536	Remote Similarity	NPD6844	Discontinued
0.6534	Remote Similarity	NPD6980	Clinical (unspecified phase)
0.6532	Remote Similarity	NPD2354	Approved
0.6522	Remote Similarity	NPD1608	Approved
0.6522	Remote Similarity	NPD7229	Phase 3
0.6514	Remote Similarity	NPD7048	Phase 3
0.6512	Remote Similarity	NPD1243	Approved
0.6508	Remote Similarity	NPD7240	Approved
0.6506	Remote Similarity	NPD3268	Approved
0.65	Remote Similarity	NPD2491	Approved
0.6491	Remote Similarity	NPD2344	Approved
0.6488	Remote Similarity	NPD5676	Approved
0.6488	Remote Similarity	NPD447	Suspended
0.6482	Remote Similarity	NPD4580	Approved
0.648	Remote Similarity	NPD7615	Clinical (unspecified phase)
0.6474	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.6474	Remote Similarity	NPD8166	Discontinued
0.6474	Remote Similarity	NPD7982	Clinical (unspecified phase)
0.6474	Remote Similarity	NPD4109	Clinical (unspecified phase)
0.6474	Remote Similarity	NPD4110	Phase 3
0.6471	Remote Similarity	NPD4308	Phase 3
0.6471	Remote Similarity	NPD8151	Discontinued

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