NPASS Compound

Structure

NPC472765 OpenBabel07101719152D 40 44 0 0 1 0 0 0 0 0999 V2000 -0.9176 -0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3668 -1.4739 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1348 -2.0101 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6348 -1.1441 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1349 -0.3508 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6158 -0.2045 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6524 -2.9792 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6245 -0.9000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.6245 -0.9000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0543 -2.4792 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4623 0.9781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1245 0.6389 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0824 -0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3668 -0.4739 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3155 0.0511 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0543 -1.4792 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.9204 -2.9792 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2054 1.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6702 -1.6180 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.0543 -0.1388 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.0000 -1.6180 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6213 -1.3090 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.3644 0.3601 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.6348 -0.4739 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.4739 -0.4739 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.6348 -1.1441 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4739 -1.1441 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.6213 -0.3090 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.6702 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.2328 0.0261 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.9204 -3.9792 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.9975 2.6254 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.0543 0.8612 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.3827 -2.5419 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.4303 -1.8968 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.7864 -2.4792 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.9335 0.0511 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5008 0.0261 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.1565 1.3383 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 13 2 0 0 0 0 2 14 1 0 0 0 0 3 26 1 0 0 0 0 4 26 1 0 0 0 0 6 28 1 0 0 0 0 7 36 1 0 0 0 0 8 9 2 0 0 0 0 8 15 1 0 0 0 0 9 37 1 0 0 0 0 10 16 1 0 0 0 0 10 17 1 0 0 0 0 11 18 1 0 0 0 0 12 15 2 0 0 0 0 12 37 1 0 0 0 0 13 29 1 0 0 0 0 14 30 2 0 0 0 0 14 38 1 0 0 0 0 15 23 1 0 0 0 0 16 26 1 0 0 0 0 16 27 1 1 0 0 0 17 31 2 0 0 0 0 17 36 1 0 0 0 0 18 32 2 0 0 0 0 18 39 1 0 0 0 0 19 13 1 1 0 0 0 19 21 1 0 0 0 0 19 22 1 0 0 0 0 20 24 1 0 0 0 0 20 25 1 0 0 0 0 20 33 1 6 0 0 0 21 27 1 0 0 0 0 21 34 2 0 0 0 0 22 28 1 1 0 0 0 22 35 1 0 0 0 0 23 28 1 1 0 0 0 23 39 1 0 0 0 0 24 26 1 0 0 0 0 24 38 1 6 0 0 0 25 27 1 6 0 0 0 25 40 1 0 0 0 0 27 5 1 1 0 0 0 28 29 1 1 0 0 0 29 11 1 1 0 0 0 29 40 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	560.23
Volume:	545.595
LogP:	2.131
LogD:	1.343
LogS:	-4.604
# Rotatable Bonds:	6
TPSA:	158.8
# H-Bond Aceptor:	11
# H-Bond Donor:	2
# Rings:	5
# Heavy Atoms:	11

MedChem Properties

QED Drug-Likeness Score:	0.411
Synthetic Accessibility Score:	6.604
Fsp3:	0.655
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:	-5.35
MDCK Permeability:	7.64E-05
Pgp-inhibitor:	0.999
Pgp-substrate:	0.996
Human Intestinal Absorption (HIA):	0.668
20% Bioavailability (F20%):	0.912
30% Bioavailability (F30%):	0.987

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.243
Plasma Protein Binding (PPB):	67.94%
Volume Distribution (VD):	0.66
Pgp-substrate:	25.62%

ADMET: Metabolism

CYP1A2-inhibitor:	0.008
CYP1A2-substrate:	0.065
CYP2C19-inhibitor:	0.025
CYP2C19-substrate:	0.316
CYP2C9-inhibitor:	0.038
CYP2C9-substrate:	0.016
CYP2D6-inhibitor:	0.017
CYP2D6-substrate:	0.067
CYP3A4-inhibitor:	0.331
CYP3A4-substrate:	0.414

ADMET: Excretion

Clearance (CL):	5.371
Half-life (T1/2):	0.502

ADMET: Toxicity

hERG Blockers:	0.029
Human Hepatotoxicity (H-HT):	0.537
Drug-inuced Liver Injury (DILI):	0.814
AMES Toxicity:	0.062
Rat Oral Acute Toxicity:	0.978
Maximum Recommended Daily Dose:	0.915
Skin Sensitization:	0.199
Carcinogencity:	0.354
Eye Corrosion:	0.004
Eye Irritation:	0.016
Respiratory Toxicity:	0.973

Download Data

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

Natural Product: NPC472765

Natural Product ID:	NPC472765
*Common Name:**	DTJCGTGRONQQPD-WIBOXGRCSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	DTJCGTGRONQQPD-WIBOXGRCSA-N
Standard InCHI:	InChI=1S/C29H36O11/c1-13-19-21(34)27(5)16(10-17(31)36-7)26(3,4)24(38-14(2)30)20(33)25(27)40-29(13)11-18(32)39-23(15-8-9-37-12-15)28(29,6)22(19)35/h8-9,12,16,19-20,22-25,33,35H,1,10-11H2,2-7H3/t16-,19-,20-,22-,23-,24+,25-,27-,28-,29-/m0/s1
SMILES:	CC(=O)OC1C(C2C(C(C1(C)C)CC(=O)OC)(C(=O)C3C(C4(C(OC(=O)CC4(C3=C)O2)C5=COC=C5)C)O)C)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3582094
PubChem CID:	n.a.
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000264] Organic acids and derivatives [CHEMONTID:0000265] Carboxylic acids and derivatives [CHEMONTID:0001986] Tricarboxylic 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
Others	2

Activity Type	# Activity
Cell Line	1
Organism	1
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT25	Cell Line	MT4	Homo sapiens	CC50	>	40000.0	nM	PMID[561984]
NPT2	Others	Unspecified		Ratio CC50/EC50	>	7.2	n.a.	PMID[561984]
NPT24	Organism	Human immunodeficiency virus 1	Human immunodeficiency virus 1	EC50	=	5500.0	nM	PMID[561984]

☑ 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 NPC472765 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	360
0.1-0.2	1429
0.2-0.3	3255
0.3-0.4	5691
0.4-0.5	10789
0.5-0.6	10199
0.6-0.7	9187
0.7-0.8	1366
0.8-0.85	293
0.85-0.9	115
0.9-0.95	6
0.95-1	7

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC472766
0.9936	High Similarity	NPC472764
0.9679	High Similarity	NPC472767
0.9497	High Similarity	NPC149945
0.9487	High Similarity	NPC195131
0.9437	High Similarity	NPC476224
0.9423	High Similarity	NPC204663
0.9371	High Similarity	NPC472773
0.9308	High Similarity	NPC472771
0.9308	High Similarity	NPC6326
0.9268	High Similarity	NPC471632
0.9198	High Similarity	NPC472774
0.9198	High Similarity	NPC472775
0.9157	High Similarity	NPC478177
0.9152	High Similarity	NPC94763
0.9152	High Similarity	NPC236004
0.9152	High Similarity	NPC471437
0.9146	High Similarity	NPC285227
0.913	High Similarity	NPC165218
0.9119	High Similarity	NPC472772
0.9085	High Similarity	NPC472659
0.9012	High Similarity	NPC472669
0.9	High Similarity	NPC167142
0.8994	High Similarity	NPC264943
0.8957	High Similarity	NPC276551
0.8951	High Similarity	NPC471166
0.8951	High Similarity	NPC471167
0.8951	High Similarity	NPC5741
0.8951	High Similarity	NPC472668
0.8935	High Similarity	NPC470938
0.8922	High Similarity	NPC469576
0.8909	High Similarity	NPC471397
0.8902	High Similarity	NPC470875
0.8896	High Similarity	NPC292389
0.8896	High Similarity	NPC469338
0.8896	High Similarity	NPC471168
0.8896	High Similarity	NPC477405
0.8889	High Similarity	NPC477402
0.8889	High Similarity	NPC470789
0.8882	High Similarity	NPC472776
0.8882	High Similarity	NPC45101
0.8882	High Similarity	NPC472778
0.8882	High Similarity	NPC197137
0.8882	High Similarity	NPC472777
0.8869	High Similarity	NPC469633
0.8848	High Similarity	NPC173516
0.8848	High Similarity	NPC472651
0.8848	High Similarity	NPC476853
0.8841	High Similarity	NPC470940
0.8841	High Similarity	NPC469849
0.8834	High Similarity	NPC200782
0.8834	High Similarity	NPC69028
0.8827	High Similarity	NPC475226
0.8827	High Similarity	NPC475967
0.8802	High Similarity	NPC159232
0.8795	High Similarity	NPC472652
0.8795	High Similarity	NPC472673
0.8795	High Similarity	NPC160651
0.8795	High Similarity	NPC327922
0.8788	High Similarity	NPC214600
0.8788	High Similarity	NPC478178
0.8779	High Similarity	NPC247563
0.8779	High Similarity	NPC105395
0.8779	High Similarity	NPC242068
0.8765	High Similarity	NPC475066
0.8765	High Similarity	NPC299038
0.8758	High Similarity	NPC469336
0.8758	High Similarity	NPC92979
0.8742	High Similarity	NPC156189
0.8735	High Similarity	NPC476861
0.8735	High Similarity	NPC472282
0.8735	High Similarity	NPC476850
0.8727	High Similarity	NPC476857
0.8727	High Similarity	NPC476856
0.8727	High Similarity	NPC123088
0.8727	High Similarity	NPC476858
0.872	High Similarity	NPC329938
0.872	High Similarity	NPC263432
0.872	High Similarity	NPC82851
0.8712	High Similarity	NPC472671
0.8712	High Similarity	NPC472779
0.8712	High Similarity	NPC477403
0.8696	High Similarity	NPC178932
0.8683	High Similarity	NPC271235
0.8679	High Similarity	NPC69647
0.8679	High Similarity	NPC472654
0.8679	High Similarity	NPC125182
0.8675	High Similarity	NPC23387
0.8675	High Similarity	NPC121995
0.8667	High Similarity	NPC663
0.8667	High Similarity	NPC224394
0.8659	High Similarity	NPC25255
0.865	High Similarity	NPC261597
0.865	High Similarity	NPC470118
0.865	High Similarity	NPC36655
0.8642	High Similarity	NPC214541
0.8642	High Similarity	NPC471175
0.8642	High Similarity	NPC44675
0.8639	High Similarity	NPC469848
0.8634	High Similarity	NPC476201
0.8634	High Similarity	NPC75906
0.8634	High Similarity	NPC469503
0.8631	High Similarity	NPC470995
0.8623	High Similarity	NPC478179
0.8614	High Similarity	NPC476860
0.8614	High Similarity	NPC259943
0.8614	High Similarity	NPC470182
0.8614	High Similarity	NPC271657
0.8606	High Similarity	NPC188649
0.8606	High Similarity	NPC193798
0.8606	High Similarity	NPC18986
0.8606	High Similarity	NPC470792
0.8598	High Similarity	NPC237155
0.8589	High Similarity	NPC175964
0.8589	High Similarity	NPC471169
0.8589	High Similarity	NPC469485
0.858	High Similarity	NPC282445
0.858	High Similarity	NPC302054
0.858	High Similarity	NPC253201
0.8571	High Similarity	NPC116717
0.8571	High Similarity	NPC18135
0.8563	High Similarity	NPC93172
0.8563	High Similarity	NPC472670
0.8563	High Similarity	NPC307781
0.8563	High Similarity	NPC97574
0.8563	High Similarity	NPC472141
0.8562	High Similarity	NPC470790
0.8562	High Similarity	NPC470791
0.8554	High Similarity	NPC476197
0.8554	High Similarity	NPC88841
0.8554	High Similarity	NPC302369
0.8554	High Similarity	NPC134254
0.8554	High Similarity	NPC288602
0.8554	High Similarity	NPC39986
0.8554	High Similarity	NPC472139
0.8553	High Similarity	NPC255414
0.8553	High Similarity	NPC470941
0.8545	High Similarity	NPC472653
0.8537	High Similarity	NPC214495
0.8537	High Similarity	NPC249021
0.8537	High Similarity	NPC470119
0.8537	High Similarity	NPC173544
0.8537	High Similarity	NPC187149
0.8528	High Similarity	NPC296807
0.8528	High Similarity	NPC155939
0.8528	High Similarity	NPC141538
0.8528	High Similarity	NPC476262
0.8521	High Similarity	NPC82602
0.8521	High Similarity	NPC472650
0.8519	High Similarity	NPC268905
0.8519	High Similarity	NPC472672
0.8519	High Similarity	NPC33938
0.8519	High Similarity	NPC84063
0.8519	High Similarity	NPC182427
0.8519	High Similarity	NPC470996
0.8519	High Similarity	NPC29695
0.8509	High Similarity	NPC196864
0.8509	High Similarity	NPC159927
0.8509	High Similarity	NPC469335
0.8509	High Similarity	NPC477404
0.8509	High Similarity	NPC470997
0.8494	Intermediate Similarity	NPC211777
0.8494	Intermediate Similarity	NPC207978
0.8494	Intermediate Similarity	NPC18347
0.8494	Intermediate Similarity	NPC149896
0.8494	Intermediate Similarity	NPC68848
0.8494	Intermediate Similarity	NPC197596
0.8494	Intermediate Similarity	NPC470939
0.8494	Intermediate Similarity	NPC5079
0.8485	Intermediate Similarity	NPC474932
0.8485	Intermediate Similarity	NPC307383
0.8471	Intermediate Similarity	NPC160818
0.8471	Intermediate Similarity	NPC169299
0.8466	Intermediate Similarity	NPC34421
0.8466	Intermediate Similarity	NPC57998
0.8466	Intermediate Similarity	NPC237259
0.8466	Intermediate Similarity	NPC98206
0.8447	Intermediate Similarity	NPC234494
0.8447	Intermediate Similarity	NPC329180
0.8447	Intermediate Similarity	NPC195325
0.8443	Intermediate Similarity	NPC285567
0.8443	Intermediate Similarity	NPC234660
0.8443	Intermediate Similarity	NPC419
0.8443	Intermediate Similarity	NPC51568
0.8443	Intermediate Similarity	NPC283209
0.8443	Intermediate Similarity	NPC198047
0.8434	Intermediate Similarity	NPC191828
0.8434	Intermediate Similarity	NPC335761
0.8434	Intermediate Similarity	NPC287559
0.8428	Intermediate Similarity	NPC5676
0.8424	Intermediate Similarity	NPC472283
0.8424	Intermediate Similarity	NPC88007
0.8424	Intermediate Similarity	NPC469847
0.8424	Intermediate Similarity	NPC194499
0.8415	Intermediate Similarity	NPC281258
0.8415	Intermediate Similarity	NPC469850
0.8402	Intermediate Similarity	NPC100333
0.8402	Intermediate Similarity	NPC270312
0.8395	Intermediate Similarity	NPC476122
0.8393	Intermediate Similarity	NPC261184

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 NPC472765 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	312
0.1-0.2	1002
0.2-0.3	2321
0.3-0.4	2712
0.4-0.5	1779
0.5-0.6	784
0.6-0.7	225
0.7-0.8	13
0.8-0.85	0
0.85-0.9	2
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8758	High Similarity	NPD5761	Phase 2
0.8758	High Similarity	NPD5760	Phase 2
0.809	Intermediate Similarity	NPD8434	Phase 2
0.7895	Intermediate Similarity	NPD5537	Clinical (unspecified phase)
0.7809	Intermediate Similarity	NPD6764	Approved
0.7809	Intermediate Similarity	NPD6765	Approved
0.7637	Intermediate Similarity	NPD6784	Approved
0.7637	Intermediate Similarity	NPD6785	Approved
0.7258	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7257	Intermediate Similarity	NPD7819	Suspended
0.7257	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7232	Intermediate Similarity	NPD7075	Discontinued
0.7228	Intermediate Similarity	NPD6559	Discontinued
0.716	Intermediate Similarity	NPD4628	Phase 3
0.7135	Intermediate Similarity	NPD7685	Pre-registration
0.711	Intermediate Similarity	NPD920	Approved
0.7086	Intermediate Similarity	NPD6599	Discontinued
0.7056	Intermediate Similarity	NPD5494	Approved
0.7045	Intermediate Similarity	NPD7411	Suspended
0.7022	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7017	Intermediate Similarity	NPD8127	Discontinued
0.7017	Intermediate Similarity	NPD7199	Phase 2
0.7017	Intermediate Similarity	NPD1247	Approved
0.7011	Intermediate Similarity	NPD7799	Discontinued
0.7011	Intermediate Similarity	NPD3818	Discontinued
0.7006	Intermediate Similarity	NPD6801	Discontinued
0.7	Intermediate Similarity	NPD919	Approved
0.6994	Remote Similarity	NPD642	Clinical (unspecified phase)
0.6989	Remote Similarity	NPD4380	Phase 2
0.6983	Remote Similarity	NPD4868	Clinical (unspecified phase)
0.6982	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.6982	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.6982	Remote Similarity	NPD6002	Phase 3
0.6982	Remote Similarity	NPD6004	Phase 3
0.6982	Remote Similarity	NPD6005	Phase 3
0.6976	Remote Similarity	NPD8404	Phase 2
0.6966	Remote Similarity	NPD2393	Clinical (unspecified phase)
0.6954	Remote Similarity	NPD6273	Approved
0.6944	Remote Similarity	NPD4381	Clinical (unspecified phase)
0.6944	Remote Similarity	NPD3749	Approved
0.6936	Remote Similarity	NPD6799	Approved
0.6927	Remote Similarity	NPD3817	Phase 2
0.691	Remote Similarity	NPD1934	Approved
0.6891	Remote Similarity	NPD7879	Clinical (unspecified phase)
0.6889	Remote Similarity	NPD3882	Suspended
0.6884	Remote Similarity	NPD7497	Discontinued
0.6882	Remote Similarity	NPD2343	Clinical (unspecified phase)
0.6882	Remote Similarity	NPD5844	Phase 1
0.6879	Remote Similarity	NPD643	Clinical (unspecified phase)
0.6879	Remote Similarity	NPD7236	Approved
0.6865	Remote Similarity	NPD7473	Discontinued
0.6864	Remote Similarity	NPD2799	Discontinued
0.6848	Remote Similarity	NPD7184	Clinical (unspecified phase)
0.6845	Remote Similarity	NPD7074	Phase 3
0.6836	Remote Similarity	NPD3226	Approved
0.6833	Remote Similarity	NPD5402	Approved
0.6811	Remote Similarity	NPD7852	Clinical (unspecified phase)
0.6811	Remote Similarity	NPD6167	Clinical (unspecified phase)
0.6811	Remote Similarity	NPD6166	Phase 2
0.6811	Remote Similarity	NPD6168	Clinical (unspecified phase)
0.6809	Remote Similarity	NPD7993	Clinical (unspecified phase)
0.6802	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.68	Remote Similarity	NPD2532	Approved
0.68	Remote Similarity	NPD2534	Approved
0.68	Remote Similarity	NPD2533	Approved
0.68	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6791	Remote Similarity	NPD7804	Clinical (unspecified phase)
0.6791	Remote Similarity	NPD7054	Approved
0.6789	Remote Similarity	NPD8313	Approved
0.6789	Remote Similarity	NPD8312	Approved
0.6784	Remote Similarity	NPD5762	Approved
0.6784	Remote Similarity	NPD5763	Approved
0.678	Remote Similarity	NPD7239	Suspended
0.6768	Remote Similarity	NPD5647	Approved
0.6763	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6755	Remote Similarity	NPD7472	Approved
0.6746	Remote Similarity	NPD6653	Approved
0.6737	Remote Similarity	NPD4338	Clinical (unspecified phase)
0.6723	Remote Similarity	NPD5403	Approved
0.6705	Remote Similarity	NPD5401	Approved
0.6705	Remote Similarity	NPD1243	Approved
0.6705	Remote Similarity	NPD2800	Approved
0.6703	Remote Similarity	NPD4965	Approved
0.6703	Remote Similarity	NPD6232	Discontinued
0.6703	Remote Similarity	NPD4967	Phase 2
0.6703	Remote Similarity	NPD4966	Approved
0.6686	Remote Similarity	NPD1471	Phase 3
0.6685	Remote Similarity	NPD2801	Approved
0.6684	Remote Similarity	NPD7251	Discontinued
0.6684	Remote Similarity	NPD8150	Discontinued
0.6667	Remote Similarity	NPD6007	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD3926	Phase 2
0.6649	Remote Similarity	NPD7228	Approved
0.6649	Remote Similarity	NPD3751	Discontinued
0.6649	Remote Similarity	NPD7808	Phase 3
0.6649	Remote Similarity	NPD7893	Clinical (unspecified phase)
0.6647	Remote Similarity	NPD970	Clinical (unspecified phase)
0.6647	Remote Similarity	NPD1549	Phase 2
0.6632	Remote Similarity	NPD6797	Phase 2
0.663	Remote Similarity	NPD37	Approved
0.663	Remote Similarity	NPD6234	Discontinued
0.6628	Remote Similarity	NPD2796	Approved
0.6613	Remote Similarity	NPD3787	Discontinued
0.661	Remote Similarity	NPD4378	Clinical (unspecified phase)
0.6593	Remote Similarity	NPD1465	Phase 2
0.659	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.659	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.659	Remote Similarity	NPD2346	Discontinued
0.6588	Remote Similarity	NPD6355	Discontinued
0.658	Remote Similarity	NPD8407	Phase 2
0.6571	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.657	Remote Similarity	NPD7033	Discontinued
0.6559	Remote Similarity	NPD6959	Discontinued
0.6552	Remote Similarity	NPD7435	Discontinued
0.6536	Remote Similarity	NPD6980	Clinical (unspecified phase)
0.6532	Remote Similarity	NPD6099	Approved
0.6532	Remote Similarity	NPD6100	Approved
0.6532	Remote Similarity	NPD1551	Phase 2
0.6529	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.6522	Remote Similarity	NPD7768	Phase 2
0.6519	Remote Similarity	NPD7028	Phase 2
0.6517	Remote Similarity	NPD7410	Clinical (unspecified phase)
0.651	Remote Similarity	NPD8368	Discontinued
0.651	Remote Similarity	NPD7240	Approved
0.6509	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6494	Remote Similarity	NPD2344	Approved
0.6491	Remote Similarity	NPD447	Suspended
0.6488	Remote Similarity	NPD6832	Phase 2
0.6477	Remote Similarity	NPD3750	Approved
0.6464	Remote Similarity	NPD7458	Discontinued
0.6464	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6461	Remote Similarity	NPD1511	Approved
0.6457	Remote Similarity	NPD2424	Discontinued
0.6455	Remote Similarity	NPD2403	Approved
0.6449	Remote Similarity	NPD7907	Approved
0.6447	Remote Similarity	NPD8397	Clinical (unspecified phase)
0.6437	Remote Similarity	NPD2935	Discontinued
0.6436	Remote Similarity	NPD5711	Approved
0.6436	Remote Similarity	NPD7229	Phase 3
0.6436	Remote Similarity	NPD6808	Phase 2
0.6436	Remote Similarity	NPD5710	Approved
0.6436	Remote Similarity	NPD7315	Approved
0.6433	Remote Similarity	NPD4140	Approved
0.6432	Remote Similarity	NPD7057	Phase 3
0.6432	Remote Similarity	NPD7058	Phase 2
0.6432	Remote Similarity	NPD4665	Approved
0.6432	Remote Similarity	NPD4111	Phase 1
0.6413	Remote Similarity	NPD8455	Phase 2
0.6412	Remote Similarity	NPD3268	Approved
0.6412	Remote Similarity	NPD2313	Discontinued
0.6407	Remote Similarity	NPD7319	Approved
0.6407	Remote Similarity	NPD6362	Approved
0.6404	Remote Similarity	NPD6778	Approved
0.6404	Remote Similarity	NPD6781	Approved
0.6404	Remote Similarity	NPD6776	Approved
0.6404	Remote Similarity	NPD6779	Approved
0.6404	Remote Similarity	NPD6780	Approved
0.6404	Remote Similarity	NPD6782	Approved
0.6404	Remote Similarity	NPD6777	Approved
0.6398	Remote Similarity	NPD7930	Approved
0.6395	Remote Similarity	NPD230	Phase 1
0.6395	Remote Similarity	NPD5735	Approved
0.6389	Remote Similarity	NPD1512	Approved
0.6389	Remote Similarity	NPD5619	Clinical (unspecified phase)
0.6384	Remote Similarity	NPD4110	Phase 3
0.6384	Remote Similarity	NPD4109	Clinical (unspecified phase)
0.6379	Remote Similarity	NPD1510	Phase 2
0.6379	Remote Similarity	NPD3748	Approved
0.6378	Remote Similarity	NPD5353	Approved
0.6373	Remote Similarity	NPD5953	Discontinued
0.6369	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD7874	Approved
0.6364	Remote Similarity	NPD7875	Clinical (unspecified phase)
0.6358	Remote Similarity	NPD6651	Approved
0.6355	Remote Similarity	NPD8285	Discontinued
0.6354	Remote Similarity	NPD7286	Phase 2
0.6348	Remote Similarity	NPD2309	Approved
0.6348	Remote Similarity	NPD6190	Approved
0.6337	Remote Similarity	NPD1240	Approved
0.6325	Remote Similarity	NPD1608	Approved
0.6324	Remote Similarity	NPD7501	Clinical (unspecified phase)
0.6322	Remote Similarity	NPD7097	Phase 1
0.6316	Remote Similarity	NPD8151	Discontinued
0.6311	Remote Similarity	NPD7698	Approved
0.6311	Remote Similarity	NPD7697	Approved
0.6311	Remote Similarity	NPD7696	Phase 3
0.6302	Remote Similarity	NPD2163	Approved
0.6298	Remote Similarity	NPD7314	Clinical (unspecified phase)
0.6281	Remote Similarity	NPD8435	Approved
0.6281	Remote Similarity	NPD8361	Approved
0.6281	Remote Similarity	NPD8360	Approved
0.628	Remote Similarity	NPD8319	Approved
0.628	Remote Similarity	NPD8320	Phase 1
0.628	Remote Similarity	NPD7870	Phase 2
0.628	Remote Similarity	NPD7871	Phase 2
0.6279	Remote Similarity	NPD8032	Phase 2
0.6268	Remote Similarity	NPD7701	Phase 2
0.6264	Remote Similarity	NPD1607	Approved
0.6262	Remote Similarity	NPD6823	Phase 2
0.6262	Remote Similarity	NPD3057	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