NPASS Compound

Structure

CID223413 OpenBabel06191716022D 40 45 0 0 1 0 0 0 0 0999 V2000 0.2569 2.3497 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0997 2.3497 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9439 0.2514 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1409 0.3609 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5325 -0.3175 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1512 1.4551 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6307 1.3136 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4214 1.1749 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0997 0.7832 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2172 0.1732 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1994 -1.2698 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7493 -0.9524 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8313 0.3439 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7831 -1.2740 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2528 -0.3175 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5128 0.8416 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4214 1.9581 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5580 0.4221 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7831 -0.7185 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.6496 -0.9524 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0997 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5499 -0.9524 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5120 0.1168 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -0.5499 -0.9524 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0997 -1.2698 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -1.2698 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6496 -0.3175 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5499 -0.3175 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6637 -0.2172 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7493 -0.3175 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1325 0.7918 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4563 0.1504 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.5499 -0.3175 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.8536 1.0905 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.0997 -2.0531 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -2.0531 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.3197 -0.3985 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.1994 0.0000 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 1.0100 0.7918 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 17 1 0 0 0 0 2 17 1 0 0 0 0 3 18 1 0 0 0 0 4 30 1 0 0 0 0 5 30 1 0 0 0 0 6 31 1 0 0 0 0 7 31 1 0 0 0 0 8 9 1 0 0 0 0 8 17 2 0 0 0 0 9 21 1 0 0 0 0 10 13 1 0 0 0 0 10 18 2 0 0 0 0 11 12 2 0 0 0 0 11 20 1 0 0 0 0 12 30 1 0 0 0 0 13 32 1 0 0 0 0 14 22 2 0 0 0 0 15 19 1 0 0 0 0 15 23 1 0 0 0 0 16 18 1 0 0 0 0 16 34 1 0 0 0 0 19 14 1 1 0 0 0 19 29 1 0 0 0 0 20 25 2 0 0 0 0 20 27 1 0 0 0 0 21 27 2 0 0 0 0 21 28 1 0 0 0 0 22 26 1 0 0 0 0 23 31 1 0 0 0 0 23 33 1 0 0 0 0 24 25 1 0 0 0 0 24 26 1 0 0 0 0 24 28 2 0 0 0 0 25 35 1 0 0 0 0 26 36 2 0 0 0 0 27 38 1 0 0 0 0 28 39 1 0 0 0 0 29 32 1 0 0 0 0 29 37 2 0 0 0 0 30 38 1 0 0 0 0 31 40 1 0 0 0 0 32 33 1 1 0 0 0 32 40 1 0 0 0 0 33 22 1 1 0 0 0 33 39 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	448.1
Volume:	413.147
LogP:	1.53
LogD:	0.622
LogS:	-4.396
# Rotatable Bonds:	3
TPSA:	190.28
# H-Bond Aceptor:	11
# H-Bond Donor:	7
# Rings:	4
# Heavy Atoms:	11

MedChem Properties

QED Drug-Likeness Score:	0.276
Synthetic Accessibility Score:	4.008
Fsp3:	0.286
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-6.223
MDCK Permeability:	7.815121534804348e-06
Pgp-inhibitor:	0.024
Pgp-substrate:	0.985
Human Intestinal Absorption (HIA):	0.372
20% Bioavailability (F20%):	0.009
30% Bioavailability (F30%):	0.994

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.011
Plasma Protein Binding (PPB):	91.96698760986328%
Volume Distribution (VD):	0.849
Pgp-substrate:	11.662840843200684%

ADMET: Metabolism

CYP1A2-inhibitor:	0.482
CYP1A2-substrate:	0.071
CYP2C19-inhibitor:	0.032
CYP2C19-substrate:	0.05
CYP2C9-inhibitor:	0.246
CYP2C9-substrate:	0.587
CYP2D6-inhibitor:	0.352
CYP2D6-substrate:	0.174
CYP3A4-inhibitor:	0.141
CYP3A4-substrate:	0.012

ADMET: Excretion

Clearance (CL):	6.124
Half-life (T1/2):	0.839

ADMET: Toxicity

hERG Blockers:	0.025
Human Hepatotoxicity (H-HT):	0.168
Drug-inuced Liver Injury (DILI):	0.98
AMES Toxicity:	0.818
Rat Oral Acute Toxicity:	0.102
Maximum Recommended Daily Dose:	0.088
Skin Sensitization:	0.92
Carcinogencity:	0.037
Eye Corrosion:	0.003
Eye Irritation:	0.817
Respiratory Toxicity:	0.061

Download Data

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

Natural Product: NPC223413

Natural Product ID:	NPC223413
*Common Name:**	UWZMGTSPGQXAAP-VHRVKJKHSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	UWZMGTSPGQXAAP-VHRVKJKHSA-N
Standard InCHI:	InChI=1S/C33H38O7/c1-17(2)8-9-21-27-20(11-12-30(4,5)38-27)25(35)24-26(36)22-14-19-15-23-31(6,7)40-32(29(19)37,13-10-18(3)16-34)33(22,23)39-28(21)24/h8,10-12,14,19,23,34-35H,9,13,15-16H2,1-7H3/b18-10+/t19-,23?,32+,33-/m0/s1
SMILES:	OC/C(=C/C[C@@]12OC(C3[C@@]42Oc2c(C(=O)C4=C[C@H](C1=O)C3)c(O)c1c(c2CC=C(C)C)OC(C=C1)(C)C)(C)C)/C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3809642
PubChem CID:	16078250
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000123] Benzopyrans [CHEMONTID:0003410] 1-benzopyrans [CHEMONTID:0002817] Dibenzopyrans [CHEMONTID:0000200] Xanthenes [CHEMONTID:0000204] Xanthones [CHEMONTID:0003521] Pyranoxanthones

*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
NPO13310	Garcinia hanburyi	Species	Clusiaceae	Eukaryota	n.a.	latex	n.a.	PMID[17117343]
NPO13310	Garcinia hanburyi	Species	Clusiaceae	Eukaryota	n.a.	fruit	n.a.	PMID[17117343]
NPO13310	Garcinia hanburyi	Species	Clusiaceae	Eukaryota	resin	n.a.	n.a.	PMID[19072548]
NPO13310	Garcinia hanburyi	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21486005]
NPO13310	Garcinia hanburyi	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO13310	Garcinia hanburyi	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO13310	Garcinia hanburyi	Species	Clusiaceae	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	2
Others	2

Activity Type	# Activity
Cell Line	2
Organism	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT81	Cell Line	A549	Homo sapiens	IC50	=	2690.0	nM	PMID[551930]
NPT71	Cell Line	HEK293	Homo sapiens	IC50	=	980.0	nM	PMID[551930]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	IZ	=	7.75	mm	PMID[551930]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	IZ	=	8.57	mm	PMID[551930]

☑ 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 NPC223413 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	412
0.1-0.2	1496
0.2-0.3	3073
0.3-0.4	6804
0.4-0.5	10981
0.5-0.6	6170
0.6-0.7	6065
0.7-0.8	6972
0.8-0.85	632
0.85-0.9	39
0.9-0.95	29
0.95-1	24

Similarity Score	Similarity Level	Natural Product ID
0.9812	High Similarity	NPC476159
0.9809	High Similarity	NPC131578
0.9618	High Similarity	NPC286422
0.9565	High Similarity	NPC75141
0.9565	High Similarity	NPC55422
0.9565	High Similarity	NPC63514
0.9565	High Similarity	NPC47634
0.9563	High Similarity	NPC476255
0.9509	High Similarity	NPC476229
0.9444	High Similarity	NPC40089
0.9444	High Similarity	NPC476146
0.9444	High Similarity	NPC158329
0.939	High Similarity	NPC476152
0.9387	High Similarity	NPC476196
0.9383	High Similarity	NPC193222
0.9379	High Similarity	NPC189689
0.9375	High Similarity	NPC94796
0.9337	High Similarity	NPC476199
0.9337	High Similarity	NPC476210
0.9329	High Similarity	NPC169018
0.9325	High Similarity	NPC476216
0.9321	High Similarity	NPC62444
0.9321	High Similarity	NPC476056
0.9277	High Similarity	NPC98943
0.9273	High Similarity	NPC476139
0.925	High Similarity	NPC43490
0.925	High Similarity	NPC475107
0.9207	High Similarity	NPC41598
0.9198	High Similarity	NPC476931
0.9172	High Similarity	NPC476162
0.9157	High Similarity	NPC475080
0.9157	High Similarity	NPC476311
0.9107	High Similarity	NPC233978
0.9102	High Similarity	NPC162248
0.9091	High Similarity	NPC102810
0.9053	High Similarity	NPC473607
0.8988	High Similarity	NPC475398
0.8982	High Similarity	NPC118128
0.8941	High Similarity	NPC473729
0.8935	High Similarity	NPC227275
0.8855	High Similarity	NPC475109
0.8841	High Similarity	NPC476929
0.8834	High Similarity	NPC125969
0.8817	High Similarity	NPC469393
0.8788	High Similarity	NPC475106
0.8773	High Similarity	NPC476930
0.8757	High Similarity	NPC477529
0.875	High Similarity	NPC54903
0.875	High Similarity	NPC286074
0.8743	High Similarity	NPC120857
0.8743	High Similarity	NPC17274
0.8743	High Similarity	NPC85047
0.8735	High Similarity	NPC469395
0.8642	High Similarity	NPC288534
0.8639	High Similarity	NPC20734
0.8631	High Similarity	NPC469394
0.8616	High Similarity	NPC82534
0.8614	High Similarity	NPC103816
0.8614	High Similarity	NPC61382
0.8588	High Similarity	NPC313717
0.8588	High Similarity	NPC315306
0.8588	High Similarity	NPC193698
0.8571	High Similarity	NPC473908
0.8537	High Similarity	NPC476169
0.8503	High Similarity	NPC472346
0.8497	Intermediate Similarity	NPC469345
0.8491	Intermediate Similarity	NPC5990
0.8488	Intermediate Similarity	NPC474276
0.8488	Intermediate Similarity	NPC147363
0.8488	Intermediate Similarity	NPC17105
0.8488	Intermediate Similarity	NPC154986
0.8488	Intermediate Similarity	NPC73899
0.8485	Intermediate Similarity	NPC164427
0.8485	Intermediate Similarity	NPC470352
0.8476	Intermediate Similarity	NPC209760
0.8476	Intermediate Similarity	NPC248793
0.8476	Intermediate Similarity	NPC311579
0.8476	Intermediate Similarity	NPC180301
0.8476	Intermediate Similarity	NPC236756
0.8476	Intermediate Similarity	NPC100134
0.8462	Intermediate Similarity	NPC314653
0.8462	Intermediate Similarity	NPC316262
0.8452	Intermediate Similarity	NPC219861
0.8448	Intermediate Similarity	NPC5671
0.8443	Intermediate Similarity	NPC472618
0.8443	Intermediate Similarity	NPC172687
0.8439	Intermediate Similarity	NPC98667
0.8439	Intermediate Similarity	NPC294149
0.8439	Intermediate Similarity	NPC232412
0.8439	Intermediate Similarity	NPC86809
0.8434	Intermediate Similarity	NPC282390
0.8434	Intermediate Similarity	NPC281137
0.8434	Intermediate Similarity	NPC201127
0.843	Intermediate Similarity	NPC472620
0.8424	Intermediate Similarity	NPC48579
0.8424	Intermediate Similarity	NPC259710
0.8424	Intermediate Similarity	NPC304207
0.8424	Intermediate Similarity	NPC207809
0.8424	Intermediate Similarity	NPC217706
0.8421	Intermediate Similarity	NPC472619
0.8415	Intermediate Similarity	NPC210597
0.8415	Intermediate Similarity	NPC470353
0.8415	Intermediate Similarity	NPC275878
0.8415	Intermediate Similarity	NPC477957
0.8415	Intermediate Similarity	NPC285623
0.8405	Intermediate Similarity	NPC471115
0.8405	Intermediate Similarity	NPC29777
0.8405	Intermediate Similarity	NPC476509
0.8402	Intermediate Similarity	NPC472581
0.84	Intermediate Similarity	NPC244903
0.8385	Intermediate Similarity	NPC329678
0.8383	Intermediate Similarity	NPC264932
0.8383	Intermediate Similarity	NPC311574
0.8382	Intermediate Similarity	NPC471969
0.8375	Intermediate Similarity	NPC18886
0.8373	Intermediate Similarity	NPC10754
0.8373	Intermediate Similarity	NPC470354
0.8373	Intermediate Similarity	NPC146636
0.8373	Intermediate Similarity	NPC20530
0.8373	Intermediate Similarity	NPC215917
0.8372	Intermediate Similarity	NPC241387
0.8372	Intermediate Similarity	NPC251144
0.8364	Intermediate Similarity	NPC7989
0.8364	Intermediate Similarity	NPC293286
0.8364	Intermediate Similarity	NPC223701
0.8364	Intermediate Similarity	NPC88983
0.8364	Intermediate Similarity	NPC469405
0.8364	Intermediate Similarity	NPC472583
0.8363	Intermediate Similarity	NPC150131
0.8363	Intermediate Similarity	NPC292233
0.8363	Intermediate Similarity	NPC476459
0.8362	Intermediate Similarity	NPC106700
0.8354	Intermediate Similarity	NPC471229
0.8354	Intermediate Similarity	NPC472580
0.8344	Intermediate Similarity	NPC470461
0.8343	Intermediate Similarity	NPC474162
0.8343	Intermediate Similarity	NPC472402
0.8343	Intermediate Similarity	NPC474150
0.8333	Intermediate Similarity	NPC313368
0.8333	Intermediate Similarity	NPC195136
0.8333	Intermediate Similarity	NPC121647
0.8333	Intermediate Similarity	NPC474108
0.8333	Intermediate Similarity	NPC177995
0.8324	Intermediate Similarity	NPC121333
0.8323	Intermediate Similarity	NPC474637
0.8323	Intermediate Similarity	NPC161650
0.8323	Intermediate Similarity	NPC210048
0.8323	Intermediate Similarity	NPC65504
0.8314	Intermediate Similarity	NPC207574
0.8314	Intermediate Similarity	NPC152477
0.8314	Intermediate Similarity	NPC288813
0.8314	Intermediate Similarity	NPC297195
0.8314	Intermediate Similarity	NPC291795
0.8313	Intermediate Similarity	NPC304745
0.8313	Intermediate Similarity	NPC204469
0.8313	Intermediate Similarity	NPC477530
0.8313	Intermediate Similarity	NPC471116
0.8313	Intermediate Similarity	NPC275575
0.8313	Intermediate Similarity	NPC276565
0.8313	Intermediate Similarity	NPC111341
0.8313	Intermediate Similarity	NPC477958
0.8305	Intermediate Similarity	NPC8927
0.8304	Intermediate Similarity	NPC82330
0.8304	Intermediate Similarity	NPC178173
0.8304	Intermediate Similarity	NPC272502
0.8304	Intermediate Similarity	NPC128293
0.8304	Intermediate Similarity	NPC120593
0.8304	Intermediate Similarity	NPC235610
0.8303	Intermediate Similarity	NPC171651
0.8303	Intermediate Similarity	NPC473996
0.8303	Intermediate Similarity	NPC216035
0.8303	Intermediate Similarity	NPC217149
0.8303	Intermediate Similarity	NPC142527
0.8303	Intermediate Similarity	NPC31627
0.8303	Intermediate Similarity	NPC476238
0.8303	Intermediate Similarity	NPC243171
0.8303	Intermediate Similarity	NPC35567
0.8303	Intermediate Similarity	NPC138288
0.8303	Intermediate Similarity	NPC327269
0.8302	Intermediate Similarity	NPC469818
0.8294	Intermediate Similarity	NPC474240
0.8294	Intermediate Similarity	NPC124038
0.8294	Intermediate Similarity	NPC472625
0.8294	Intermediate Similarity	NPC109180
0.8294	Intermediate Similarity	NPC473009
0.8293	Intermediate Similarity	NPC267117
0.8293	Intermediate Similarity	NPC470908
0.8293	Intermediate Similarity	NPC105136
0.8293	Intermediate Similarity	NPC61258
0.8284	Intermediate Similarity	NPC3629
0.8284	Intermediate Similarity	NPC117985
0.8284	Intermediate Similarity	NPC478134
0.8282	Intermediate Similarity	NPC296869
0.8282	Intermediate Similarity	NPC266572
0.8282	Intermediate Similarity	NPC160821
0.8282	Intermediate Similarity	NPC39195
0.8282	Intermediate Similarity	NPC6511
0.8282	Intermediate Similarity	NPC145467
0.8282	Intermediate Similarity	NPC470460
0.8282	Intermediate Similarity	NPC132592

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 NPC223413 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	352
0.1-0.2	923
0.2-0.3	1834
0.3-0.4	2681
0.4-0.5	1939
0.5-0.6	963
0.6-0.7	315
0.7-0.8	137
0.8-0.85	6
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8313	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.8214	Intermediate Similarity	NPD7075	Discontinued
0.8208	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.8155	Intermediate Similarity	NPD3882	Suspended
0.8144	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8098	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.8072	Intermediate Similarity	NPD4380	Phase 2
0.8036	Intermediate Similarity	NPD7819	Suspended
0.8012	Intermediate Similarity	NPD2800	Approved
0.8012	Intermediate Similarity	NPD5494	Approved
0.7988	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7988	Intermediate Similarity	NPD2534	Approved
0.7988	Intermediate Similarity	NPD2533	Approved
0.7988	Intermediate Similarity	NPD2532	Approved
0.7976	Intermediate Similarity	NPD6801	Discontinued
0.7931	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7931	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7931	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7931	Intermediate Similarity	NPD6166	Phase 2
0.7929	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7921	Intermediate Similarity	NPD7808	Phase 3
0.7917	Intermediate Similarity	NPD7411	Suspended
0.7865	Intermediate Similarity	NPD7251	Discontinued
0.7861	Intermediate Similarity	NPD1247	Approved
0.7809	Intermediate Similarity	NPD6797	Phase 2
0.7791	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7772	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7765	Intermediate Similarity	NPD1934	Approved
0.7759	Intermediate Similarity	NPD6959	Discontinued
0.7751	Intermediate Similarity	NPD6599	Discontinued
0.7747	Intermediate Similarity	NPD8434	Phase 2
0.774	Intermediate Similarity	NPD3818	Discontinued
0.773	Intermediate Similarity	NPD1549	Phase 2
0.7719	Intermediate Similarity	NPD2801	Approved
0.7711	Intermediate Similarity	NPD6799	Approved
0.7697	Intermediate Similarity	NPD7054	Approved
0.7688	Intermediate Similarity	NPD3749	Approved
0.7684	Intermediate Similarity	NPD7473	Discontinued
0.7674	Intermediate Similarity	NPD3817	Phase 2
0.7669	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7669	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7654	Intermediate Similarity	NPD7074	Phase 3
0.7654	Intermediate Similarity	NPD1510	Phase 2
0.7654	Intermediate Similarity	NPD7472	Approved
0.765	Intermediate Similarity	NPD8150	Discontinued
0.7644	Intermediate Similarity	NPD919	Approved
0.764	Intermediate Similarity	NPD6651	Approved
0.763	Intermediate Similarity	NPD7768	Phase 2
0.7624	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7619	Intermediate Similarity	NPD1512	Approved
0.7607	Intermediate Similarity	NPD2796	Approved
0.7598	Intermediate Similarity	NPD5844	Phase 1
0.7574	Intermediate Similarity	NPD5403	Approved
0.7572	Intermediate Similarity	NPD5402	Approved
0.7569	Intermediate Similarity	NPD6559	Discontinued
0.7543	Intermediate Similarity	NPD5537	Clinical (unspecified phase)
0.7542	Intermediate Similarity	NPD3751	Discontinued
0.753	Intermediate Similarity	NPD3750	Approved
0.7528	Intermediate Similarity	NPD2403	Approved
0.7515	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7514	Intermediate Similarity	NPD5711	Approved
0.7514	Intermediate Similarity	NPD5710	Approved
0.7514	Intermediate Similarity	NPD6232	Discontinued
0.7514	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD1511	Approved
0.7456	Intermediate Similarity	NPD5401	Approved
0.7432	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7429	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7425	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7423	Intermediate Similarity	NPD1607	Approved
0.7407	Intermediate Similarity	NPD1240	Approved
0.7405	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7394	Intermediate Similarity	NPD6100	Approved
0.7394	Intermediate Similarity	NPD6099	Approved
0.7391	Intermediate Similarity	NPD8313	Approved
0.7391	Intermediate Similarity	NPD8312	Approved
0.7374	Intermediate Similarity	NPD3926	Phase 2
0.7368	Intermediate Similarity	NPD920	Approved
0.7365	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7362	Intermediate Similarity	NPD5124	Phase 1
0.7362	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.733	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7318	Intermediate Similarity	NPD3787	Discontinued
0.7306	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7287	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7283	Intermediate Similarity	NPD3226	Approved
0.7282	Intermediate Similarity	NPD7697	Approved
0.7282	Intermediate Similarity	NPD7696	Phase 3
0.7282	Intermediate Similarity	NPD7435	Discontinued
0.7282	Intermediate Similarity	NPD7698	Approved
0.7262	Intermediate Similarity	NPD1243	Approved
0.7251	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7246	Intermediate Similarity	NPD1471	Phase 3
0.7245	Intermediate Similarity	NPD7870	Phase 2
0.7245	Intermediate Similarity	NPD7871	Phase 2
0.7235	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7229	Intermediate Similarity	NPD3748	Approved
0.7219	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7216	Intermediate Similarity	NPD6777	Approved
0.7216	Intermediate Similarity	NPD6780	Approved
0.7216	Intermediate Similarity	NPD6776	Approved
0.7216	Intermediate Similarity	NPD6781	Approved
0.7216	Intermediate Similarity	NPD6779	Approved
0.7216	Intermediate Similarity	NPD6782	Approved
0.7216	Intermediate Similarity	NPD6778	Approved
0.715	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.715	Intermediate Similarity	NPD7874	Approved
0.7143	Intermediate Similarity	NPD2346	Discontinued
0.7143	Intermediate Similarity	NPD2344	Approved
0.7136	Intermediate Similarity	NPD8366	Approved
0.7136	Intermediate Similarity	NPD7701	Phase 2
0.7126	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7126	Intermediate Similarity	NPD2799	Discontinued
0.7119	Intermediate Similarity	NPD1465	Phase 2
0.7119	Intermediate Similarity	NPD5761	Phase 2
0.7119	Intermediate Similarity	NPD5760	Phase 2
0.7118	Intermediate Similarity	NPD4628	Phase 3
0.7114	Intermediate Similarity	NPD7801	Approved
0.7113	Intermediate Similarity	NPD7700	Phase 2
0.7113	Intermediate Similarity	NPD7699	Phase 2
0.71	Intermediate Similarity	NPD8151	Discontinued
0.7088	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7086	Intermediate Similarity	NPD7458	Discontinued
0.7083	Intermediate Similarity	NPD1551	Phase 2
0.7073	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7073	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7071	Intermediate Similarity	NPD8319	Approved
0.7071	Intermediate Similarity	NPD8320	Phase 1
0.7065	Intermediate Similarity	NPD7228	Approved
0.7053	Intermediate Similarity	NPD7907	Approved
0.7047	Intermediate Similarity	NPD4360	Phase 2
0.7047	Intermediate Similarity	NPD6535	Approved
0.7047	Intermediate Similarity	NPD6534	Approved
0.7047	Intermediate Similarity	NPD4363	Phase 3
0.7043	Intermediate Similarity	NPD5953	Discontinued
0.7027	Intermediate Similarity	NPD7286	Phase 2
0.701	Intermediate Similarity	NPD4361	Phase 2
0.701	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD8491	Approved
0.6994	Remote Similarity	NPD7390	Discontinued
0.699	Remote Similarity	NPD8285	Discontinued
0.6989	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6982	Remote Similarity	NPD2935	Discontinued
0.6978	Remote Similarity	NPD7199	Phase 2
0.6977	Remote Similarity	NPD2309	Approved
0.6973	Remote Similarity	NPD7893	Clinical (unspecified phase)
0.697	Remote Similarity	NPD2313	Discontinued
0.697	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6967	Remote Similarity	NPD8469	Approved
0.6966	Remote Similarity	NPD37	Approved
0.6957	Remote Similarity	NPD4665	Approved
0.6957	Remote Similarity	NPD4111	Phase 1
0.6954	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6951	Remote Similarity	NPD4908	Phase 1
0.6946	Remote Similarity	NPD7783	Phase 2
0.6946	Remote Similarity	NPD7782	Clinical (unspecified phase)
0.6944	Remote Similarity	NPD4965	Approved
0.6944	Remote Similarity	NPD4967	Phase 2
0.6944	Remote Similarity	NPD4966	Approved
0.694	Remote Similarity	NPD7229	Phase 3
0.6927	Remote Similarity	NPD4287	Approved
0.6923	Remote Similarity	NPD651	Clinical (unspecified phase)
0.6915	Remote Similarity	NPD7584	Approved
0.6915	Remote Similarity	NPD7685	Pre-registration
0.6915	Remote Similarity	NPD6765	Approved
0.6915	Remote Similarity	NPD6764	Approved
0.6886	Remote Similarity	NPD943	Approved
0.6884	Remote Similarity	NPD6823	Phase 2
0.6884	Remote Similarity	NPD3057	Approved
0.6875	Remote Similarity	NPD6980	Clinical (unspecified phase)
0.6868	Remote Similarity	NPD6234	Discontinued
0.6867	Remote Similarity	NPD3268	Approved
0.6865	Remote Similarity	NPD7784	Clinical (unspecified phase)
0.6852	Remote Similarity	NPD4749	Approved
0.6845	Remote Similarity	NPD6355	Discontinued
0.6824	Remote Similarity	NPD7033	Discontinued
0.681	Remote Similarity	NPD8155	Clinical (unspecified phase)
0.6807	Remote Similarity	NPD4625	Phase 3
0.6802	Remote Similarity	NPD2424	Discontinued
0.68	Remote Similarity	NPD2972	Approved
0.68	Remote Similarity	NPD3533	Approved
0.6793	Remote Similarity	NPD8127	Discontinued
0.6791	Remote Similarity	NPD7799	Discontinued
0.6786	Remote Similarity	NPD4060	Phase 1
0.6771	Remote Similarity	NPD6784	Approved
0.6771	Remote Similarity	NPD6785	Approved
0.6746	Remote Similarity	NPD447	Suspended
0.6746	Remote Similarity	NPD230	Phase 1
0.6745	Remote Similarity	NPD5619	Clinical (unspecified phase)
0.6744	Remote Similarity	NPD2343	Clinical (unspecified phase)
0.6743	Remote Similarity	NPD7236	Approved
0.6743	Remote Similarity	NPD3300	Phase 2
0.674	Remote Similarity	NPD8455	Phase 2
0.6737	Remote Similarity	NPD7240	Approved
0.6728	Remote Similarity	NPD1610	Phase 2
0.6727	Remote Similarity	NPD2798	Approved
0.6724	Remote Similarity	NPD7003	Approved
0.6724	Remote Similarity	NPD8166	Discontinued
0.6723	Remote Similarity	NPD6273	Approved
0.6722	Remote Similarity	NPD5890	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