NPASS Compound

Structure

CID108342 OpenBabel06191715462D 23 27 0 0 0 0 0 0 0 0999 V2000 -1.8385 1.8891 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4184 0.0189 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4061 -0.9107 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1973 -3.6667 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9926 -4.1251 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6056 -2.2761 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8084 0.0401 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9139 0.0961 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1925 -2.7392 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6195 0.4942 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5950 -1.3648 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7961 -0.8894 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6048 -1.3583 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9883 -2.2797 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9955 -1.3516 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7984 -2.7423 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5990 -2.2801 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1911 -0.8989 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7885 -3.6657 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -3.3999 -2.7401 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.6317 1.4171 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.2877 -0.7434 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 3 2 0 0 0 0 2 10 1 0 0 0 0 3 11 1 0 0 0 0 4 5 2 0 0 0 0 4 9 1 0 0 0 0 5 19 1 0 0 0 0 6 9 2 0 0 0 0 6 13 1 0 0 0 0 7 10 2 0 0 0 0 7 12 1 0 0 0 0 8 22 1 0 0 0 0 8 23 1 0 0 0 0 9 14 1 0 0 0 0 10 21 1 0 0 0 0 11 12 2 0 0 0 0 11 17 1 0 0 0 0 12 15 1 0 0 0 0 13 18 2 0 0 0 0 13 22 1 0 0 0 0 14 15 2 0 0 0 0 14 16 1 0 0 0 0 15 18 1 0 0 0 0 16 17 1 0 0 0 0 16 19 2 0 0 0 0 17 20 2 0 0 0 0 18 23 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	305.07
Volume:	299.531
LogP:	3.855
LogD:	3.037
LogS:	-6.671
# Rotatable Bonds:	1
TPSA:	57.65
# H-Bond Aceptor:	5
# H-Bond Donor:	0
# Rings:	5
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.54
Synthetic Accessibility Score:	2.604
Fsp3:	0.111
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.863
MDCK Permeability:	2.297316495969426e-05
Pgp-inhibitor:	0.356
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.002
20% Bioavailability (F20%):	0.001
30% Bioavailability (F30%):	0.071

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.218
Plasma Protein Binding (PPB):	97.28585052490234%
Volume Distribution (VD):	0.713
Pgp-substrate:	1.8587013483047485%

ADMET: Metabolism

CYP1A2-inhibitor:	0.965
CYP1A2-substrate:	0.437
CYP2C19-inhibitor:	0.927
CYP2C19-substrate:	0.126
CYP2C9-inhibitor:	0.726
CYP2C9-substrate:	0.914
CYP2D6-inhibitor:	0.743
CYP2D6-substrate:	0.899
CYP3A4-inhibitor:	0.854
CYP3A4-substrate:	0.152

ADMET: Excretion

Clearance (CL):	11.365
Half-life (T1/2):	0.136

ADMET: Toxicity

hERG Blockers:	0.07
Human Hepatotoxicity (H-HT):	0.306
Drug-inuced Liver Injury (DILI):	0.944
AMES Toxicity:	0.908
Rat Oral Acute Toxicity:	0.044
Maximum Recommended Daily Dose:	0.929
Skin Sensitization:	0.074
Carcinogencity:	0.955
Eye Corrosion:	0.004
Eye Irritation:	0.397
Respiratory Toxicity:	0.882

Download Data

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

Natural Product: NPC108342

Natural Product ID:	NPC108342
*Common Name:**	BHFUORVSBHCRKK-UHFFFAOYSA-N
IUPAC Name:	n.a.
Synonyms:	10-Methoxyliriodenine
Standard InCHIKey:	BHFUORVSBHCRKK-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C18H11NO4/c1-21-10-2-3-11-12(7-10)15-14-9(4-5-19-16(14)17(11)20)6-13-18(15)23-8-22-13/h2-7H,8H2,1H3
SMILES:	COc1ccc2c(c1)c1c3OCOc3cc3c1c(C2=O)ncc3
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL471281
PubChem CID:	73104
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000279] Alkaloids and derivatives [CHEMONTID:0000381] Aporphines

*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
NPO7140	Millettia taiwaniana	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15270565]
NPO16209	Garcinia brasiliensis	Species	Clusiaceae	Eukaryota	n.a.	pericarp	n.a.	PMID[17562491]
NPO16209	Garcinia brasiliensis	Species	Clusiaceae	Eukaryota	n.a.	fruit	n.a.	PMID[17562491]
NPO16455	Xylopia aethiopica	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[8158166]
NPO33359	miliusa cf. banacea	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[8158166]
NPO2239	Mahonia manipurensis	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[HerDing]
NPO2239	Mahonia manipurensis	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[TCMID]
NPO16455	Xylopia aethiopica	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4942	Scenedesmus acutus	Species	Scenedesmaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3947	Corydalis sheareri	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16209	Garcinia brasiliensis	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1683	Abies magnifica	Species	Pinaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2239	Mahonia manipurensis	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO7140	Millettia taiwaniana	Species	Fabaceae	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
Others	2

Activity Type	# Activity
Individual Protein	1
Organism	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1044	Individual Protein	DNA topoisomerase II alpha	Homo sapiens	IC50	=	25.0	ug.mL-1	PMID[527981]
NPT312	Organism	Saccharomyces cerevisiae	Saccharomyces cerevisiae	Activity	=	113.0	ug ml-1	PMID[527981]
NPT312	Organism	Saccharomyces cerevisiae	Saccharomyces cerevisiae	Activity	=	214.0	ug ml-1	PMID[527981]

☑ 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 NPC108342 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	629
0.1-0.2	2710
0.2-0.3	10496
0.3-0.4	6643
0.4-0.5	9556
0.5-0.6	10473
0.6-0.7	1868
0.7-0.8	244
0.8-0.85	55
0.85-0.9	5
0.9-0.95	7
0.95-1	11

Similarity Score	Similarity Level	Natural Product ID
0.9952	High Similarity	NPC189903
0.9952	High Similarity	NPC182907
0.981	High Similarity	NPC166722
0.9809	High Similarity	NPC22481
0.976	High Similarity	NPC278525
0.9718	High Similarity	NPC210296
0.9674	High Similarity	NPC124313
0.9673	High Similarity	NPC84164
0.9673	High Similarity	NPC207283
0.9571	High Similarity	NPC24019
0.9471	High Similarity	NPC210434
0.9455	High Similarity	NPC183537
0.939	High Similarity	NPC233334
0.9367	High Similarity	NPC77878
0.9302	High Similarity	NPC90875
0.9095	High Similarity	NPC15406
0.8995	High Similarity	NPC236668
0.8952	High Similarity	NPC146976
0.8768	High Similarity	NPC251160
0.861	High Similarity	NPC253675
0.8585	High Similarity	NPC470020
0.8502	High Similarity	NPC119134
0.8442	Intermediate Similarity	NPC270515
0.8426	Intermediate Similarity	NPC235076
0.8411	Intermediate Similarity	NPC188420
0.8333	Intermediate Similarity	NPC477019
0.8311	Intermediate Similarity	NPC23614
0.8311	Intermediate Similarity	NPC100079
0.8295	Intermediate Similarity	NPC271215
0.8295	Intermediate Similarity	NPC149471
0.8288	Intermediate Similarity	NPC322482
0.8273	Intermediate Similarity	NPC46451
0.8249	Intermediate Similarity	NPC53069
0.8249	Intermediate Similarity	NPC202768
0.8249	Intermediate Similarity	NPC296482
0.8246	Intermediate Similarity	NPC234197
0.8186	Intermediate Similarity	NPC478045
0.8186	Intermediate Similarity	NPC313189
0.8165	Intermediate Similarity	NPC96405
0.8165	Intermediate Similarity	NPC171409
0.8161	Intermediate Similarity	NPC118121
0.8161	Intermediate Similarity	NPC122463
0.8145	Intermediate Similarity	NPC204446
0.8133	Intermediate Similarity	NPC470018
0.8102	Intermediate Similarity	NPC135549
0.8097	Intermediate Similarity	NPC74575
0.8086	Intermediate Similarity	NPC195268
0.8086	Intermediate Similarity	NPC133140
0.8025	Intermediate Similarity	NPC132385
0.8	Intermediate Similarity	NPC216612
0.7983	Intermediate Similarity	NPC137353
0.7957	Intermediate Similarity	NPC49547
0.7931	Intermediate Similarity	NPC470017
0.7928	Intermediate Similarity	NPC55470
0.7926	Intermediate Similarity	NPC476581
0.7926	Intermediate Similarity	NPC36229
0.7926	Intermediate Similarity	NPC16452
0.7897	Intermediate Similarity	NPC470022
0.786	Intermediate Similarity	NPC476582
0.786	Intermediate Similarity	NPC4071
0.786	Intermediate Similarity	NPC476578
0.7832	Intermediate Similarity	NPC174049
0.7826	Intermediate Similarity	NPC246381
0.7788	Intermediate Similarity	NPC31930
0.7773	Intermediate Similarity	NPC193238
0.7753	Intermediate Similarity	NPC54066
0.7718	Intermediate Similarity	NPC134637
0.7705	Intermediate Similarity	NPC318068
0.7699	Intermediate Similarity	NPC208522
0.7689	Intermediate Similarity	NPC72905
0.7679	Intermediate Similarity	NPC202605
0.7679	Intermediate Similarity	NPC112206
0.7668	Intermediate Similarity	NPC290689
0.7665	Intermediate Similarity	NPC473822
0.7657	Intermediate Similarity	NPC142385
0.765	Intermediate Similarity	NPC471004
0.765	Intermediate Similarity	NPC23080
0.765	Intermediate Similarity	NPC193906
0.7642	Intermediate Similarity	NPC129897
0.7634	Intermediate Similarity	NPC220337
0.7613	Intermediate Similarity	NPC308943
0.7605	Intermediate Similarity	NPC41501
0.7593	Intermediate Similarity	NPC107123
0.754	Intermediate Similarity	NPC191489
0.7534	Intermediate Similarity	NPC5374
0.75	Intermediate Similarity	NPC94842
0.7488	Intermediate Similarity	NPC312531
0.7488	Intermediate Similarity	NPC206201
0.7469	Intermediate Similarity	NPC302807
0.7468	Intermediate Similarity	NPC255800
0.7468	Intermediate Similarity	NPC96584
0.7458	Intermediate Similarity	NPC201508
0.7457	Intermediate Similarity	NPC477788
0.7455	Intermediate Similarity	NPC222561
0.7449	Intermediate Similarity	NPC303374
0.743	Intermediate Similarity	NPC204385
0.7427	Intermediate Similarity	NPC148889
0.7425	Intermediate Similarity	NPC122436
0.7421	Intermediate Similarity	NPC315634
0.7421	Intermediate Similarity	NPC100734
0.7421	Intermediate Similarity	NPC88923
0.7419	Intermediate Similarity	NPC13603
0.7409	Intermediate Similarity	NPC71124
0.7385	Intermediate Similarity	NPC254957
0.7383	Intermediate Similarity	NPC249405
0.7379	Intermediate Similarity	NPC326930
0.7379	Intermediate Similarity	NPC85879
0.7379	Intermediate Similarity	NPC475301
0.7379	Intermediate Similarity	NPC53255
0.7375	Intermediate Similarity	NPC235685
0.7364	Intermediate Similarity	NPC224928
0.7362	Intermediate Similarity	NPC473506
0.7352	Intermediate Similarity	NPC146724
0.7347	Intermediate Similarity	NPC1608
0.7344	Intermediate Similarity	NPC101350
0.7341	Intermediate Similarity	NPC328928
0.7339	Intermediate Similarity	NPC280799
0.7336	Intermediate Similarity	NPC232225
0.7331	Intermediate Similarity	NPC122968
0.7331	Intermediate Similarity	NPC473833
0.7331	Intermediate Similarity	NPC477787
0.7331	Intermediate Similarity	NPC328186
0.7331	Intermediate Similarity	NPC475631
0.7331	Intermediate Similarity	NPC476110
0.7331	Intermediate Similarity	NPC87152
0.7331	Intermediate Similarity	NPC228377
0.7331	Intermediate Similarity	NPC89549
0.7331	Intermediate Similarity	NPC475600
0.733	Intermediate Similarity	NPC127085
0.7325	Intermediate Similarity	NPC208284
0.7321	Intermediate Similarity	NPC207971
0.7314	Intermediate Similarity	NPC253482
0.7311	Intermediate Similarity	NPC316841
0.7311	Intermediate Similarity	NPC475303
0.7311	Intermediate Similarity	NPC292416
0.7311	Intermediate Similarity	NPC475596
0.7311	Intermediate Similarity	NPC473689
0.7304	Intermediate Similarity	NPC4421
0.7303	Intermediate Similarity	NPC472061
0.73	Intermediate Similarity	NPC475644
0.73	Intermediate Similarity	NPC470486
0.73	Intermediate Similarity	NPC471977
0.73	Intermediate Similarity	NPC471190
0.7296	Intermediate Similarity	NPC469439
0.7295	Intermediate Similarity	NPC475648
0.7292	Intermediate Similarity	NPC475406
0.7289	Intermediate Similarity	NPC268077
0.7284	Intermediate Similarity	NPC473115
0.7284	Intermediate Similarity	NPC158020
0.7284	Intermediate Similarity	NPC6576
0.7284	Intermediate Similarity	NPC212768
0.7284	Intermediate Similarity	NPC217554
0.7284	Intermediate Similarity	NPC473089
0.7284	Intermediate Similarity	NPC75600
0.7281	Intermediate Similarity	NPC474009
0.728	Intermediate Similarity	NPC244839
0.728	Intermediate Similarity	NPC319880
0.728	Intermediate Similarity	NPC320324
0.728	Intermediate Similarity	NPC30456
0.7265	Intermediate Similarity	NPC284141
0.7261	Intermediate Similarity	NPC327904
0.7261	Intermediate Similarity	NPC38959
0.7257	Intermediate Similarity	NPC300156
0.7256	Intermediate Similarity	NPC179704
0.7255	Intermediate Similarity	NPC470042
0.725	Intermediate Similarity	NPC237702
0.725	Intermediate Similarity	NPC329631
0.7243	Intermediate Similarity	NPC168922
0.7238	Intermediate Similarity	NPC260434
0.7238	Intermediate Similarity	NPC476999
0.7238	Intermediate Similarity	NPC474688
0.7229	Intermediate Similarity	NPC298449
0.7222	Intermediate Similarity	NPC284685
0.722	Intermediate Similarity	NPC327769
0.7216	Intermediate Similarity	NPC9482
0.7213	Intermediate Similarity	NPC475844
0.7212	Intermediate Similarity	NPC38961
0.7206	Intermediate Similarity	NPC324619
0.7206	Intermediate Similarity	NPC475315
0.7203	Intermediate Similarity	NPC76565
0.7203	Intermediate Similarity	NPC250807
0.7203	Intermediate Similarity	NPC57797
0.7202	Intermediate Similarity	NPC11408
0.7196	Intermediate Similarity	NPC287588
0.7193	Intermediate Similarity	NPC100573
0.7193	Intermediate Similarity	NPC82548
0.7193	Intermediate Similarity	NPC207873
0.7191	Intermediate Similarity	NPC477903
0.7186	Intermediate Similarity	NPC162530
0.7186	Intermediate Similarity	NPC324361
0.7186	Intermediate Similarity	NPC266931
0.7185	Intermediate Similarity	NPC146824
0.7185	Intermediate Similarity	NPC478078
0.7181	Intermediate Similarity	NPC45190
0.7179	Intermediate Similarity	NPC301368
0.7179	Intermediate Similarity	NPC84815
0.7179	Intermediate Similarity	NPC74360
0.7173	Intermediate Similarity	NPC475498
0.7173	Intermediate Similarity	NPC473850
0.7173	Intermediate Similarity	NPC328154

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 NPC108342 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	370
0.1-0.2	649
0.2-0.3	957
0.3-0.4	1658
0.4-0.5	2628
0.5-0.6	2153
0.6-0.7	676
0.7-0.8	54
0.8-0.85	5
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8273	Intermediate Similarity	NPD3763	Approved
0.8249	Intermediate Similarity	NPD3815	Phase 1
0.8249	Intermediate Similarity	NPD3816	Phase 1
0.8086	Intermediate Similarity	NPD3922	Approved
0.8086	Intermediate Similarity	NPD3923	Approved
0.8086	Intermediate Similarity	NPD3924	Approved
0.8086	Intermediate Similarity	NPD3921	Approved
0.7992	Intermediate Similarity	NPD4926	Clinical (unspecified phase)
0.7679	Intermediate Similarity	NPD7885	Phase 2
0.7679	Intermediate Similarity	NPD7886	Phase 2
0.7673	Intermediate Similarity	NPD8091	Phase 3
0.7647	Intermediate Similarity	NPD6790	Phase 1
0.7644	Intermediate Similarity	NPD7571	Clinical (unspecified phase)
0.76	Intermediate Similarity	NPD7069	Discontinued
0.7574	Intermediate Similarity	NPD4885	Approved
0.7564	Intermediate Similarity	NPD5801	Clinical (unspecified phase)
0.756	Intermediate Similarity	NPD3920	Phase 2
0.754	Intermediate Similarity	NPD7708	Approved
0.7531	Intermediate Similarity	NPD8350	Clinical (unspecified phase)
0.7521	Intermediate Similarity	NPD5805	Approved
0.75	Intermediate Similarity	NPD6525	Clinical (unspecified phase)
0.7469	Intermediate Similarity	NPD1483	Discontinued
0.7468	Intermediate Similarity	NPD6494	Phase 2
0.7446	Intermediate Similarity	NPD6242	Discontinued
0.7421	Intermediate Similarity	NPD7803	Approved
0.7371	Intermediate Similarity	NPD7862	Clinical (unspecified phase)
0.7368	Intermediate Similarity	NPD5866	Approved
0.7359	Intermediate Similarity	NPD7395	Discontinued
0.7359	Intermediate Similarity	NPD6568	Discontinued
0.7358	Intermediate Similarity	NPD5482	Discontinued
0.7315	Intermediate Similarity	NPD6257	Clinical (unspecified phase)
0.7292	Intermediate Similarity	NPD6964	Approved
0.7292	Intermediate Similarity	NPD6963	Approved
0.7273	Intermediate Similarity	NPD6727	Phase 2
0.7265	Intermediate Similarity	NPD5483	Clinical (unspecified phase)
0.725	Intermediate Similarity	NPD5040	Clinical (unspecified phase)
0.725	Intermediate Similarity	NPD6741	Clinical (unspecified phase)
0.7241	Intermediate Similarity	NPD4989	Phase 2
0.7236	Intermediate Similarity	NPD5488	Discontinued
0.7222	Intermediate Similarity	NPD7955	Approved
0.7222	Intermediate Similarity	NPD4889	Approved
0.7222	Intermediate Similarity	NPD7956	Approved
0.7213	Intermediate Similarity	NPD7417	Discontinued
0.721	Intermediate Similarity	NPD4429	Discontinued
0.72	Intermediate Similarity	NPD6477	Clinical (unspecified phase)
0.7184	Intermediate Similarity	NPD6716	Phase 1
0.7172	Intermediate Similarity	NPD2921	Clinical (unspecified phase)
0.7167	Intermediate Similarity	NPD3326	Clinical (unspecified phase)
0.7166	Intermediate Similarity	NPD6460	Clinical (unspecified phase)
0.7163	Intermediate Similarity	NPD7414	Clinical (unspecified phase)
0.7149	Intermediate Similarity	NPD5429	Discontinued
0.7126	Intermediate Similarity	NPD6531	Approved
0.7126	Intermediate Similarity	NPD6530	Approved
0.7125	Intermediate Similarity	NPD4952	Phase 3
0.7125	Intermediate Similarity	NPD8052	Clinical (unspecified phase)
0.7101	Intermediate Similarity	NPD6247	Clinical (unspecified phase)
0.71	Intermediate Similarity	NPD7927	Clinical (unspecified phase)
0.7099	Intermediate Similarity	NPD3217	Phase 2
0.7076	Intermediate Similarity	NPD8479	Phase 2
0.7064	Intermediate Similarity	NPD3354	Phase 2
0.7059	Intermediate Similarity	NPD6228	Discontinued
0.7054	Intermediate Similarity	NPD5022	Discontinued
0.7049	Intermediate Similarity	NPD3006	Discontinued
0.7047	Intermediate Similarity	NPD7169	Suspended
0.7045	Intermediate Similarity	NPD6517	Phase 3
0.7043	Intermediate Similarity	NPD5658	Approved
0.7042	Intermediate Similarity	NPD3259	Approved
0.704	Intermediate Similarity	NPD4418	Discontinued
0.7037	Intermediate Similarity	NPD4373	Phase 2
0.7018	Intermediate Similarity	NPD5513	Phase 2
0.7017	Intermediate Similarity	NPD2285	Clinical (unspecified phase)
0.7016	Intermediate Similarity	NPD5450	Discontinued
0.7012	Intermediate Similarity	NPD7588	Discontinued
0.7009	Intermediate Similarity	NPD1923	Clinical (unspecified phase)
0.7005	Intermediate Similarity	NPD3386	Phase 2
0.7	Intermediate Similarity	NPD3263	Phase 3
0.7	Intermediate Similarity	NPD7426	Phase 1
0.6988	Remote Similarity	NPD6230	Discontinued
0.6987	Remote Similarity	NPD7278	Phase 2
0.6987	Remote Similarity	NPD7279	Phase 2
0.6987	Remote Similarity	NPD3946	Clinical (unspecified phase)
0.6983	Remote Similarity	NPD5914	Approved
0.6983	Remote Similarity	NPD4997	Clinical (unspecified phase)
0.6973	Remote Similarity	NPD5459	Phase 2
0.697	Remote Similarity	NPD4859	Phase 1
0.6962	Remote Similarity	NPD5519	Discontinued
0.696	Remote Similarity	NPD6219	Discontinued
0.696	Remote Similarity	NPD8468	Phase 2
0.6957	Remote Similarity	NPD7010	Phase 3
0.6955	Remote Similarity	NPD6962	Phase 2
0.6936	Remote Similarity	NPD3257	Approved
0.692	Remote Similarity	NPD5632	Approved
0.6911	Remote Similarity	NPD5891	Approved
0.6907	Remote Similarity	NPD8149	Discontinued
0.6905	Remote Similarity	NPD4558	Phase 2
0.6904	Remote Similarity	NPD4923	Phase 1
0.6901	Remote Similarity	NPD7268	Clinical (unspecified phase)
0.6901	Remote Similarity	NPD7994	Phase 2
0.6898	Remote Similarity	NPD7558	Phase 2
0.6897	Remote Similarity	NPD7467	Discontinued
0.6895	Remote Similarity	NPD8016	Phase 3
0.6895	Remote Similarity	NPD8017	Clinical (unspecified phase)
0.689	Remote Similarity	NPD7859	Phase 2
0.6883	Remote Similarity	NPD5530	Phase 1
0.6878	Remote Similarity	NPD4375	Approved
0.6875	Remote Similarity	NPD6569	Phase 2
0.6875	Remote Similarity	NPD6160	Clinical (unspecified phase)
0.6872	Remote Similarity	NPD7710	Clinical (unspecified phase)
0.6862	Remote Similarity	NPD5850	Phase 3
0.6862	Remote Similarity	NPD5930	Phase 3
0.6861	Remote Similarity	NPD6281	Approved
0.686	Remote Similarity	NPD5640	Discontinued
0.6858	Remote Similarity	NPD7673	Phase 3
0.6853	Remote Similarity	NPD7222	Phase 2
0.6851	Remote Similarity	NPD7225	Discontinued
0.685	Remote Similarity	NPD6503	Clinical (unspecified phase)
0.684	Remote Similarity	NPD4037	Approved
0.684	Remote Similarity	NPD4038	Approved
0.684	Remote Similarity	NPD31	Approved
0.684	Remote Similarity	NPD4039	Approved
0.684	Remote Similarity	NPD4036	Approved
0.684	Remote Similarity	NPD4035	Approved
0.684	Remote Similarity	NPD4033	Approved
0.684	Remote Similarity	NPD4034	Approved
0.684	Remote Similarity	NPD32	Approved
0.684	Remote Similarity	NPD4122	Approved
0.6837	Remote Similarity	NPD1078	Clinical (unspecified phase)
0.6835	Remote Similarity	NPD1620	Clinical (unspecified phase)
0.683	Remote Similarity	NPD2334	Discontinued
0.6825	Remote Similarity	NPD8100	Phase 3
0.682	Remote Similarity	NPD3258	Approved
0.682	Remote Similarity	NPD6974	Phase 3
0.6816	Remote Similarity	NPD1505	Phase 2
0.6814	Remote Similarity	NPD5975	Clinical (unspecified phase)
0.6812	Remote Similarity	NPD4396	Clinical (unspecified phase)
0.681	Remote Similarity	NPD5601	Phase 2
0.6803	Remote Similarity	NPD7555	Discontinued
0.6796	Remote Similarity	NPD8279	Clinical (unspecified phase)
0.6795	Remote Similarity	NPD5867	Clinical (unspecified phase)
0.6793	Remote Similarity	NPD7538	Clinical (unspecified phase)
0.6792	Remote Similarity	NPD7180	Phase 3
0.6787	Remote Similarity	NPD6825	Phase 1
0.6787	Remote Similarity	NPD6745	Discontinued
0.6784	Remote Similarity	NPD6550	Discontinued
0.6784	Remote Similarity	NPD5512	Phase 3
0.6776	Remote Similarity	NPD7567	Approved
0.6773	Remote Similarity	NPD4875	Phase 3
0.6773	Remote Similarity	NPD4876	Phase 3
0.677	Remote Similarity	NPD1038	Approved
0.677	Remote Similarity	NPD4551	Phase 2
0.677	Remote Similarity	NPD1304	Clinical (unspecified phase)
0.6768	Remote Similarity	NPD7924	Phase 2
0.6768	Remote Similarity	NPD7925	Phase 2
0.6765	Remote Similarity	NPD5612	Discontinued
0.6765	Remote Similarity	NPD2433	Clinical (unspecified phase)
0.6762	Remote Similarity	NPD4845	Discontinued
0.6762	Remote Similarity	NPD4328	Approved
0.6762	Remote Similarity	NPD6553	Clinical (unspecified phase)
0.6753	Remote Similarity	NPD6975	Discontinued
0.6745	Remote Similarity	NPD8101	Phase 3
0.6744	Remote Similarity	NPD6872	Clinical (unspecified phase)
0.6741	Remote Similarity	NPD7233	Approved
0.6741	Remote Similarity	NPD7234	Approved
0.6738	Remote Similarity	NPD2060	Approved
0.6737	Remote Similarity	NPD7703	Clinical (unspecified phase)
0.6737	Remote Similarity	NPD6567	Clinical (unspecified phase)
0.6736	Remote Similarity	NPD6824	Clinical (unspecified phase)
0.6734	Remote Similarity	NPD7807	Clinical (unspecified phase)
0.6732	Remote Similarity	NPD8463	Approved
0.6732	Remote Similarity	NPD3328	Phase 2
0.6732	Remote Similarity	NPD8358	Approved
0.6732	Remote Similarity	NPD5532	Phase 2
0.6732	Remote Similarity	NPD6276	Discontinued
0.6729	Remote Similarity	NPD2782	Approved
0.6729	Remote Similarity	NPD2780	Approved
0.6723	Remote Similarity	NPD4667	Clinical (unspecified phase)
0.6722	Remote Similarity	NPD5070	Clinical (unspecified phase)
0.672	Remote Similarity	NPD7729	Clinical (unspecified phase)
0.6708	Remote Similarity	NPD7547	Clinical (unspecified phase)
0.6707	Remote Similarity	NPD5479	Discontinued
0.6707	Remote Similarity	NPD7853	Phase 2
0.6706	Remote Similarity	NPD8102	Discontinued
0.6703	Remote Similarity	NPD7690	Clinical (unspecified phase)
0.6696	Remote Similarity	NPD6361	Phase 2
0.6696	Remote Similarity	NPD4118	Clinical (unspecified phase)
0.6695	Remote Similarity	NPD3393	Approved
0.6695	Remote Similarity	NPD4795	Phase 2
0.6695	Remote Similarity	NPD6138	Clinical (unspecified phase)
0.6695	Remote Similarity	NPD3947	Discontinued
0.6695	Remote Similarity	NPD3394	Approved
0.6695	Remote Similarity	NPD6987	Phase 1
0.6695	Remote Similarity	NPD3389	Approved
0.6694	Remote Similarity	NPD6298	Discontinued
0.6692	Remote Similarity	NPD7689	Approved
0.6681	Remote Similarity	NPD2739	Clinical (unspecified phase)
0.6681	Remote Similarity	NPD3945	Discontinued
0.668	Remote Similarity	NPD4958	Clinical (unspecified phase)
0.668	Remote Similarity	NPD3925	Approved
0.668	Remote Similarity	NPD4846	Phase 2
0.6667	Remote Similarity	NPD4502	Phase 2

Bioactivity similarity: Similar Natural Products in NPASS

Bioactivity similarity was calculated based on bioactivity descriptors of compounds. The bioactivity descriptors were calculated by a recently developed AI algorithm Chemical Checker (CC) [Nature Biotechnology, 38:1087–1096, 2020; Nature Communications, 12:3932, 2021], which evaluated bioactivity similarities at five levels:
☉ A: chemistry similarity;
☉ B: biological targets similarity;
☉ C: networks similarity;
☉ D: cell-based bioactivity similarity;
☉ E: similarity based on clinical data.

Those 5 categories of CC bioactivity descriptors were calculated and then subjected to manifold projection using UMAP algorithm, to project all NPs on a 2-Dimensional space. The current NP was highlighted with a small circle in the 2-D map. Below figures: left-to-right, A-to-E.

A: chemistry similarity

B: biological targets similarity

C: networks similarity

D: cell-based bioactivity similarity

E: similarity based on clinical data