NPASS Compound

Structure

NPC159232 OpenBabel07101719252D 37 42 0 0 1 0 0 0 0 0999 V2000 -1.3262 0.5905 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9003 -0.1997 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1517 -3.0242 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0407 -1.5804 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9003 -0.1997 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5324 -4.0295 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3489 -2.5571 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0513 -3.9796 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.7789 -0.6948 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1948 -2.0688 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7772 -3.3260 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.4325 -1.4206 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9887 -2.0634 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8866 -1.0920 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5031 -2.0688 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8776 -3.6777 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0407 -0.6037 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.3489 0.3731 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.1948 0.8615 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9289 -1.2786 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9289 -0.3018 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5741 -2.3706 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.1948 -1.0920 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.5031 -1.0920 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0000 -1.5804 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.3489 -0.6037 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.5741 -0.7902 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.0807 -2.7223 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.1948 1.8382 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7191 -1.8527 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.5741 -2.3706 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7223 0.7902 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.6035 -4.3313 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.9441 -2.2665 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.0407 0.3731 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.5031 -0.1153 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 21 1 0 0 0 0 2 21 1 0 0 0 0 3 22 1 0 0 0 0 4 23 1 0 0 0 0 5 24 1 0 0 0 0 6 33 1 0 0 0 0 7 10 1 0 0 0 0 7 15 1 0 0 0 0 8 11 2 0 0 0 0 8 16 1 0 0 0 0 9 12 2 0 0 0 0 9 14 1 0 0 0 0 10 23 1 0 0 0 0 11 22 1 0 0 0 0 12 34 1 0 0 0 0 13 14 2 0 0 0 0 13 34 1 0 0 0 0 14 17 1 0 0 0 0 15 22 1 6 0 0 0 15 24 1 0 0 0 0 16 28 2 0 0 0 0 16 33 1 0 0 0 0 17 23 1 1 0 0 0 17 35 1 0 0 0 0 18 19 1 0 0 0 0 18 26 1 6 0 0 0 18 36 1 0 0 0 0 19 29 2 0 0 0 0 19 35 1 0 0 0 0 20 21 1 0 0 0 0 20 25 1 0 0 0 0 20 30 2 0 0 0 0 21 37 1 0 0 0 0 22 25 1 1 0 0 0 23 26 1 1 0 0 0 24 26 1 1 0 0 0 25 27 1 6 0 0 0 25 31 1 0 0 0 0 26 36 1 6 0 0 0 27 24 1 1 0 0 0 27 32 1 0 0 0 0 27 37 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	516.2
Volume:	496.293
LogP:	2.901
LogD:	2.217
LogS:	-4.685
# Rotatable Bonds:	4
TPSA:	145.03
# H-Bond Aceptor:	10
# H-Bond Donor:	2
# Rings:	6
# Heavy Atoms:	10

MedChem Properties

QED Drug-Likeness Score:	0.347
Synthetic Accessibility Score:	6.043
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:	-5.428
MDCK Permeability:	1.6832093024277128e-05
Pgp-inhibitor:	0.715
Pgp-substrate:	0.233
Human Intestinal Absorption (HIA):	0.685
20% Bioavailability (F20%):	0.995
30% Bioavailability (F30%):	0.912

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.972
Plasma Protein Binding (PPB):	77.14347839355469%
Volume Distribution (VD):	1.489
Pgp-substrate:	26.133256912231445%

ADMET: Metabolism

CYP1A2-inhibitor:	0.022
CYP1A2-substrate:	0.935
CYP2C19-inhibitor:	0.093
CYP2C19-substrate:	0.775
CYP2C9-inhibitor:	0.234
CYP2C9-substrate:	0.001
CYP2D6-inhibitor:	0.002
CYP2D6-substrate:	0.065
CYP3A4-inhibitor:	0.79
CYP3A4-substrate:	0.888

ADMET: Excretion

Clearance (CL):	5.34
Half-life (T1/2):	0.338

ADMET: Toxicity

hERG Blockers:	0.018
Human Hepatotoxicity (H-HT):	0.657
Drug-inuced Liver Injury (DILI):	0.875
AMES Toxicity:	0.541
Rat Oral Acute Toxicity:	0.99
Maximum Recommended Daily Dose:	0.951
Skin Sensitization:	0.337
Carcinogencity:	0.958
Eye Corrosion:	0.003
Eye Irritation:	0.019
Respiratory Toxicity:	0.965

Download Data

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

Natural Product: NPC159232

Natural Product ID:	NPC159232
*Common Name:**	Harrisonin
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	DYNIRWNERRSOEV-HPGFDZHLSA-N
Standard InCHI:	InChI=1S/C27H32O10/c1-21(2)20(30)25(31)22(3,11-8-16(28)33-6)15-7-10-23(4)17(14-9-12-34-13-14)35-19(29)18-26(23,36-18)24(15,5)27(25,32)37-21/h8-9,11-13,15,17-18,31-32H,7,10H2,1-6H3/b11-8-/t15-,17+,18-,22-,23+,24-,25+,26-,27+/m1/s1
SMILES:	CC1(C)C(=O)[C@@]2([C@](C)(/C=CC(=O)OC)[C@H]3CC[C@@]4(C)[C@H](c5ccoc5)OC(=O)[C@@H]5[C@@]4([C@]3(C)[C@]2(O)O1)O5)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2398516
PubChem CID:	5281308
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
NPO21362	Harrisonia perforata	Species	Rutaceae	Eukaryota	n.a.	root	n.a.	PMID[16394547]
NPO21362	Harrisonia perforata	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23688954]
NPO21362	Harrisonia perforata	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO21362	Harrisonia perforata	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO21362	Harrisonia perforata	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO21362	Harrisonia perforata	Species	Rutaceae	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

Activity Type	# Activity
NON-MOLECULAR	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	134540.0	nM	PMID[496930]

☑ 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 NPC159232 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	384
0.1-0.2	1505
0.2-0.3	3416
0.3-0.4	6083
0.4-0.5	11339
0.5-0.6	10473
0.6-0.7	8332
0.7-0.8	884
0.8-0.85	179
0.85-0.9	84
0.9-0.95	17
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9379	High Similarity	NPC214600
0.9273	High Similarity	NPC236004
0.9162	High Similarity	NPC478177
0.9157	High Similarity	NPC94763
0.9141	High Similarity	NPC478178
0.9118	High Similarity	NPC247563
0.9118	High Similarity	NPC242068
0.9118	High Similarity	NPC105395
0.908	High Similarity	NPC123088
0.9053	High Similarity	NPC470938
0.9012	High Similarity	NPC25255
0.8976	High Similarity	NPC472659
0.897	High Similarity	NPC472651
0.897	High Similarity	NPC476861
0.897	High Similarity	NPC478179
0.897	High Similarity	NPC476850
0.8957	High Similarity	NPC193798
0.8929	High Similarity	NPC471437
0.8929	High Similarity	NPC469576
0.8922	High Similarity	NPC285227
0.8916	High Similarity	NPC472652
0.8916	High Similarity	NPC327922
0.8916	High Similarity	NPC271235
0.8902	High Similarity	NPC165218
0.8896	High Similarity	NPC472653
0.8889	High Similarity	NPC187149
0.8882	High Similarity	NPC44675
0.8882	High Similarity	NPC214541
0.8876	High Similarity	NPC469633
0.8869	High Similarity	NPC469848
0.8848	High Similarity	NPC476858
0.8848	High Similarity	NPC476856
0.8848	High Similarity	NPC476857
0.8841	High Similarity	NPC5079
0.8834	High Similarity	NPC477403
0.881	High Similarity	NPC169299
0.881	High Similarity	NPC160818
0.8802	High Similarity	NPC472766
0.8802	High Similarity	NPC472765
0.8795	High Similarity	NPC149945
0.8788	High Similarity	NPC134254
0.8788	High Similarity	NPC302369
0.8788	High Similarity	NPC234660
0.8788	High Similarity	NPC39986
0.8788	High Similarity	NPC471168
0.8788	High Similarity	NPC51568
0.878	High Similarity	NPC477402
0.878	High Similarity	NPC335761
0.878	High Similarity	NPC305016
0.8773	High Similarity	NPC261597
0.8773	High Similarity	NPC299038
0.8773	High Similarity	NPC36655
0.8773	High Similarity	NPC45101
0.8773	High Similarity	NPC286722
0.875	High Similarity	NPC470995
0.875	High Similarity	NPC82602
0.8743	High Similarity	NPC472282
0.8743	High Similarity	NPC173516
0.8743	High Similarity	NPC476224
0.8743	High Similarity	NPC476853
0.8743	High Similarity	NPC472764
0.8735	High Similarity	NPC476860
0.8727	High Similarity	NPC472767
0.8727	High Similarity	NPC117986
0.8727	High Similarity	NPC472668
0.8727	High Similarity	NPC197596
0.8727	High Similarity	NPC6326
0.872	High Similarity	NPC475295
0.872	High Similarity	NPC237155
0.872	High Similarity	NPC475967
0.872	High Similarity	NPC473473
0.8712	High Similarity	NPC126723
0.8712	High Similarity	NPC209364
0.8712	High Similarity	NPC107646
0.8696	High Similarity	NPC18135
0.869	High Similarity	NPC160651
0.869	High Similarity	NPC242334
0.869	High Similarity	NPC471397
0.8683	High Similarity	NPC472141
0.8683	High Similarity	NPC23387
0.8675	High Similarity	NPC472139
0.8675	High Similarity	NPC469846
0.8675	High Similarity	NPC472669
0.8675	High Similarity	NPC477405
0.8675	High Similarity	NPC292389
0.8675	High Similarity	NPC469338
0.8667	High Similarity	NPC470789
0.8667	High Similarity	NPC475381
0.8667	High Similarity	NPC191828
0.8659	High Similarity	NPC470118
0.865	High Similarity	NPC264943
0.8642	High Similarity	NPC75906
0.8623	High Similarity	NPC470940
0.8623	High Similarity	NPC271657
0.8623	High Similarity	NPC276551
0.8623	High Similarity	NPC469849
0.8614	High Similarity	NPC82851
0.8614	High Similarity	NPC96443
0.8614	High Similarity	NPC18347
0.8614	High Similarity	NPC329938
0.8614	High Similarity	NPC471167
0.8614	High Similarity	NPC69028
0.8614	High Similarity	NPC471166
0.8614	High Similarity	NPC149896
0.8614	High Similarity	NPC290400
0.8614	High Similarity	NPC263432
0.8614	High Similarity	NPC207978
0.8614	High Similarity	NPC470939
0.8606	High Similarity	NPC475226
0.8606	High Similarity	NPC474932
0.8605	High Similarity	NPC470181
0.8598	High Similarity	NPC263265
0.8598	High Similarity	NPC469485
0.8598	High Similarity	NPC204663
0.8598	High Similarity	NPC60973
0.8596	High Similarity	NPC471632
0.8589	High Similarity	NPC57998
0.858	High Similarity	NPC472673
0.8571	High Similarity	NPC470875
0.8563	High Similarity	NPC419
0.8563	High Similarity	NPC663
0.8563	High Similarity	NPC224394
0.8562	High Similarity	NPC221809
0.8547	High Similarity	NPC262386
0.8545	High Similarity	NPC173544
0.8545	High Similarity	NPC249021
0.8545	High Similarity	NPC197137
0.8545	High Similarity	NPC195131
0.8529	High Similarity	NPC472650
0.8528	High Similarity	NPC268905
0.8521	High Similarity	NPC472774
0.8521	High Similarity	NPC100333
0.8521	High Similarity	NPC472775
0.8512	High Similarity	NPC259943
0.8512	High Similarity	NPC470182
0.8512	High Similarity	NPC261184
0.8503	High Similarity	NPC5741
0.8503	High Similarity	NPC211777
0.8494	Intermediate Similarity	NPC262872
0.8494	Intermediate Similarity	NPC307383
0.8491	Intermediate Similarity	NPC86935
0.8457	Intermediate Similarity	NPC195325
0.8457	Intermediate Similarity	NPC472654
0.8452	Intermediate Similarity	NPC198047
0.8452	Intermediate Similarity	NPC472773
0.8434	Intermediate Similarity	NPC472776
0.8434	Intermediate Similarity	NPC472283
0.8434	Intermediate Similarity	NPC472777
0.8434	Intermediate Similarity	NPC472778
0.8424	Intermediate Similarity	NPC141538
0.8424	Intermediate Similarity	NPC296807
0.8424	Intermediate Similarity	NPC155939
0.8415	Intermediate Similarity	NPC44577
0.8412	Intermediate Similarity	NPC473766
0.8412	Intermediate Similarity	NPC473753
0.8405	Intermediate Similarity	NPC156189
0.8402	Intermediate Similarity	NPC146991
0.8393	Intermediate Similarity	NPC200782
0.8393	Intermediate Similarity	NPC472771
0.8393	Intermediate Similarity	NPC470792
0.8385	Intermediate Similarity	NPC346
0.8383	Intermediate Similarity	NPC472671
0.8383	Intermediate Similarity	NPC472779
0.8382	Intermediate Similarity	NPC477824
0.8364	Intermediate Similarity	NPC282445
0.8364	Intermediate Similarity	NPC30222
0.8354	Intermediate Similarity	NPC116717
0.8353	Intermediate Similarity	NPC472670
0.8353	Intermediate Similarity	NPC307781
0.8353	Intermediate Similarity	NPC97574
0.8353	Intermediate Similarity	NPC93172
0.8333	Intermediate Similarity	NPC250228
0.8333	Intermediate Similarity	NPC470941
0.8323	Intermediate Similarity	NPC472772
0.8323	Intermediate Similarity	NPC214495
0.8323	Intermediate Similarity	NPC475066
0.8323	Intermediate Similarity	NPC470119
0.8313	Intermediate Similarity	NPC471175
0.8313	Intermediate Similarity	NPC281258
0.8313	Intermediate Similarity	NPC35000
0.8313	Intermediate Similarity	NPC469850
0.8313	Intermediate Similarity	NPC469336
0.8303	Intermediate Similarity	NPC476939
0.8303	Intermediate Similarity	NPC84063
0.8303	Intermediate Similarity	NPC476940
0.8303	Intermediate Similarity	NPC476201
0.8303	Intermediate Similarity	NPC469503
0.8303	Intermediate Similarity	NPC147168
0.8284	Intermediate Similarity	NPC188649
0.8282	Intermediate Similarity	NPC7388
0.8274	Intermediate Similarity	NPC84349
0.8274	Intermediate Similarity	NPC116639
0.8263	Intermediate Similarity	NPC175964
0.8263	Intermediate Similarity	NPC471169
0.8261	Intermediate Similarity	NPC137295
0.8261	Intermediate Similarity	NPC251865
0.8253	Intermediate Similarity	NPC34421
0.8253	Intermediate Similarity	NPC237259
0.8253	Intermediate Similarity	NPC178932
0.8253	Intermediate Similarity	NPC98206

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 NPC159232 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	321
0.1-0.2	1046
0.2-0.3	2362
0.3-0.4	2796
0.4-0.5	1711
0.5-0.6	690
0.6-0.7	211
0.7-0.8	11
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
0.8424	Intermediate Similarity	NPD5761	Phase 2
0.8424	Intermediate Similarity	NPD5760	Phase 2
0.7907	Intermediate Similarity	NPD5537	Clinical (unspecified phase)
0.7821	Intermediate Similarity	NPD6765	Approved
0.7821	Intermediate Similarity	NPD6764	Approved
0.7802	Intermediate Similarity	NPD8434	Phase 2
0.765	Intermediate Similarity	NPD6785	Approved
0.765	Intermediate Similarity	NPD6784	Approved
0.7403	Intermediate Similarity	NPD7799	Discontinued
0.7273	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7247	Intermediate Similarity	NPD7075	Discontinued
0.72	Intermediate Similarity	NPD6599	Discontinued
0.7151	Intermediate Similarity	NPD6559	Discontinued
0.7151	Intermediate Similarity	NPD7685	Pre-registration
0.7083	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD5762	Approved
0.7	Intermediate Similarity	NPD5763	Approved
0.6994	Remote Similarity	NPD7236	Approved
0.699	Remote Similarity	NPD8404	Phase 2
0.6983	Remote Similarity	NPD7819	Suspended
0.6977	Remote Similarity	NPD4628	Phase 3
0.6957	Remote Similarity	NPD7184	Clinical (unspecified phase)
0.6954	Remote Similarity	NPD6799	Approved
0.6927	Remote Similarity	NPD6801	Discontinued
0.6923	Remote Similarity	NPD919	Approved
0.6898	Remote Similarity	NPD7804	Clinical (unspecified phase)
0.6895	Remote Similarity	NPD8312	Approved
0.6895	Remote Similarity	NPD8313	Approved
0.6893	Remote Similarity	NPD7239	Suspended
0.6851	Remote Similarity	NPD3817	Phase 2
0.6851	Remote Similarity	NPD5402	Approved
0.6845	Remote Similarity	NPD3751	Discontinued
0.6836	Remote Similarity	NPD920	Approved
0.6813	Remote Similarity	NPD3882	Suspended
0.6811	Remote Similarity	NPD3787	Discontinued
0.6802	Remote Similarity	NPD2343	Clinical (unspecified phase)
0.678	Remote Similarity	NPD6273	Approved
0.6776	Remote Similarity	NPD4381	Clinical (unspecified phase)
0.6757	Remote Similarity	NPD1247	Approved
0.6757	Remote Similarity	NPD7199	Phase 2
0.6757	Remote Similarity	NPD8127	Discontinued
0.6755	Remote Similarity	NPD3818	Discontinued
0.6754	Remote Similarity	NPD4338	Clinical (unspecified phase)
0.6746	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.6742	Remote Similarity	NPD5403	Approved
0.6733	Remote Similarity	NPD7497	Discontinued
0.6733	Remote Similarity	NPD7435	Discontinued
0.6723	Remote Similarity	NPD642	Clinical (unspecified phase)
0.6723	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6723	Remote Similarity	NPD5401	Approved
0.6706	Remote Similarity	NPD6355	Discontinued
0.6705	Remote Similarity	NPD6002	Phase 3
0.6705	Remote Similarity	NPD6005	Phase 3
0.6705	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.6705	Remote Similarity	NPD1471	Phase 3
0.6705	Remote Similarity	NPD6004	Phase 3
0.6705	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.6703	Remote Similarity	NPD5494	Approved
0.6702	Remote Similarity	NPD7251	Discontinued
0.6701	Remote Similarity	NPD8150	Discontinued
0.6686	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6685	Remote Similarity	NPD3749	Approved
0.6684	Remote Similarity	NPD8407	Phase 2
0.6667	Remote Similarity	NPD3226	Approved
0.6667	Remote Similarity	NPD7808	Phase 3
0.6649	Remote Similarity	NPD6797	Phase 2
0.6649	Remote Similarity	NPD6234	Discontinued
0.663	Remote Similarity	NPD4965	Approved
0.663	Remote Similarity	NPD4380	Phase 2
0.663	Remote Similarity	NPD4966	Approved
0.663	Remote Similarity	NPD4868	Clinical (unspecified phase)
0.663	Remote Similarity	NPD4967	Phase 2
0.6629	Remote Similarity	NPD2532	Approved
0.6629	Remote Similarity	NPD2533	Approved
0.6629	Remote Similarity	NPD2534	Approved
0.6615	Remote Similarity	NPD8368	Discontinued
0.6614	Remote Similarity	NPD7473	Discontinued
0.6612	Remote Similarity	NPD2393	Clinical (unspecified phase)
0.661	Remote Similarity	NPD643	Clinical (unspecified phase)
0.6609	Remote Similarity	NPD2346	Discontinued
0.6597	Remote Similarity	NPD7074	Phase 3
0.6593	Remote Similarity	NPD7411	Suspended
0.6587	Remote Similarity	NPD5647	Approved
0.6579	Remote Similarity	NPD7228	Approved
0.6576	Remote Similarity	NPD8443	Clinical (unspecified phase)
0.6575	Remote Similarity	NPD7458	Discontinued
0.6561	Remote Similarity	NPD6168	Clinical (unspecified phase)
0.6561	Remote Similarity	NPD6166	Phase 2
0.6561	Remote Similarity	NPD6167	Clinical (unspecified phase)
0.6558	Remote Similarity	NPD5619	Clinical (unspecified phase)
0.6557	Remote Similarity	NPD1934	Approved
0.6545	Remote Similarity	NPD5844	Phase 1
0.6545	Remote Similarity	NPD7054	Approved
0.6541	Remote Similarity	NPD7058	Phase 2
0.6541	Remote Similarity	NPD7057	Phase 3
0.6538	Remote Similarity	NPD7875	Clinical (unspecified phase)
0.6538	Remote Similarity	NPD7874	Approved
0.6538	Remote Similarity	NPD7028	Phase 2
0.6536	Remote Similarity	NPD4378	Clinical (unspecified phase)
0.6527	Remote Similarity	NPD1049	Clinical (unspecified phase)
0.651	Remote Similarity	NPD7472	Approved
0.6508	Remote Similarity	NPD3926	Phase 2
0.6502	Remote Similarity	NPD6778	Approved
0.6502	Remote Similarity	NPD6780	Approved
0.6502	Remote Similarity	NPD6782	Approved
0.6502	Remote Similarity	NPD6776	Approved
0.6502	Remote Similarity	NPD6779	Approved
0.6502	Remote Similarity	NPD6777	Approved
0.6502	Remote Similarity	NPD6781	Approved
0.6494	Remote Similarity	NPD2799	Discontinued
0.6493	Remote Similarity	NPD7930	Approved
0.6477	Remote Similarity	NPD7993	Clinical (unspecified phase)
0.6474	Remote Similarity	NPD6653	Approved
0.6467	Remote Similarity	NPD37	Approved
0.6465	Remote Similarity	NPD8397	Clinical (unspecified phase)
0.6465	Remote Similarity	NPD7907	Approved
0.6457	Remote Similarity	NPD6099	Approved
0.6457	Remote Similarity	NPD6100	Approved
0.6457	Remote Similarity	NPD1551	Phase 2
0.6456	Remote Similarity	NPD8320	Phase 1
0.6456	Remote Similarity	NPD8319	Approved
0.6455	Remote Similarity	NPD6232	Discontinued
0.6443	Remote Similarity	NPD7240	Approved
0.6441	Remote Similarity	NPD1243	Approved
0.6441	Remote Similarity	NPD2800	Approved
0.6441	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6412	Remote Similarity	NPD6832	Phase 2
0.6408	Remote Similarity	NPD7698	Approved
0.6408	Remote Similarity	NPD7696	Phase 3
0.6408	Remote Similarity	NPD7697	Approved
0.6407	Remote Similarity	NPD7078	Approved
0.6406	Remote Similarity	NPD7893	Clinical (unspecified phase)
0.6404	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.6402	Remote Similarity	NPD6959	Discontinued
0.64	Remote Similarity	NPD7033	Discontinued
0.6393	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6391	Remote Similarity	NPD6007	Clinical (unspecified phase)
0.6387	Remote Similarity	NPD7852	Clinical (unspecified phase)
0.6386	Remote Similarity	NPD7492	Approved
0.6384	Remote Similarity	NPD1549	Phase 2
0.6384	Remote Similarity	NPD970	Clinical (unspecified phase)
0.6382	Remote Similarity	NPD8435	Approved
0.6377	Remote Similarity	NPD7871	Phase 2
0.6377	Remote Similarity	NPD7870	Phase 2
0.6374	Remote Similarity	NPD6980	Clinical (unspecified phase)
0.6373	Remote Similarity	NPD8285	Discontinued
0.6372	Remote Similarity	NPD4111	Phase 1
0.6364	Remote Similarity	NPD2796	Approved
0.6364	Remote Similarity	NPD8424	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD7701	Phase 2
0.6351	Remote Similarity	NPD7801	Approved
0.6347	Remote Similarity	NPD6616	Approved
0.6346	Remote Similarity	NPD7999	Approved
0.6344	Remote Similarity	NPD8455	Phase 2
0.6344	Remote Similarity	NPD2801	Approved
0.6343	Remote Similarity	NPD7097	Phase 1
0.6341	Remote Similarity	NPD6054	Approved
0.6341	Remote Similarity	NPD4107	Approved
0.6337	Remote Similarity	NPD2313	Discontinued
0.6331	Remote Similarity	NPD7319	Approved
0.6328	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6328	Remote Similarity	NPD2344	Approved
0.6328	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.6322	Remote Similarity	NPD447	Suspended
0.6322	Remote Similarity	NPD5735	Approved
0.63	Remote Similarity	NPD8361	Approved
0.63	Remote Similarity	NPD8360	Approved
0.6298	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6296	Remote Similarity	NPD4665	Approved
0.6283	Remote Similarity	NPD7315	Approved
0.6283	Remote Similarity	NPD5711	Approved
0.6283	Remote Similarity	NPD5710	Approved
0.628	Remote Similarity	NPD3057	Approved
0.6279	Remote Similarity	NPD7095	Approved
0.6278	Remote Similarity	NPD2354	Approved
0.6278	Remote Similarity	NPD3887	Approved
0.6277	Remote Similarity	NPD7768	Phase 2
0.6274	Remote Similarity	NPD7783	Phase 2
0.6274	Remote Similarity	NPD7782	Clinical (unspecified phase)
0.6272	Remote Similarity	NPD7736	Approved
0.6271	Remote Similarity	NPD2935	Discontinued
0.6265	Remote Similarity	NPD6370	Approved
0.6264	Remote Similarity	NPD4140	Approved
0.6264	Remote Similarity	NPD7410	Clinical (unspecified phase)
0.6257	Remote Similarity	NPD1465	Phase 2
0.6256	Remote Similarity	NPD6534	Approved
0.6256	Remote Similarity	NPD6535	Approved
0.625	Remote Similarity	NPD7507	Approved
0.625	Remote Similarity	NPD1608	Approved
0.6244	Remote Similarity	NPD7699	Phase 2
0.6244	Remote Similarity	NPD7700	Phase 2
0.6243	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6243	Remote Similarity	NPD6798	Discontinued
0.6243	Remote Similarity	NPD1699	Clinical (unspecified phase)
0.6242	Remote Similarity	NPD6319	Approved
0.6239	Remote Similarity	NPD8155	Clinical (unspecified phase)
0.6238	Remote Similarity	NPD7296	Approved
0.6232	Remote Similarity	NPD4482	Phase 3
0.623	Remote Similarity	NPD1512	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