NPASS Compound

Structure

NPC472323 OpenBabel07101719522D 28 31 0 0 1 0 0 0 0 0999 V2000 -4.9676 3.0109 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9836 1.9316 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3090 -0.9511 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6831 1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6831 0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8171 1.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8171 -0.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3118 1.1627 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4067 2.5316 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1541 1.1839 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7049 3.3868 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9731 2.9064 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9511 1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5663 1.9929 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -2.5718 1.8883 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 -2.1666 2.5441 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.9511 0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4013 2.6361 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.5823 0.9135 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.1486 1.2884 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5878 0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9890 1.8271 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -2.2443 4.2744 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.3853 3.7154 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.7364 0.4794 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.5554 2.2019 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 12 1 0 0 0 0 2 23 1 0 0 0 0 3 24 1 0 0 0 0 4 5 2 0 0 0 0 4 6 1 0 0 0 0 5 7 1 0 0 0 0 6 13 2 0 0 0 0 7 18 2 0 0 0 0 8 15 1 0 0 0 0 9 16 1 0 0 0 0 10 14 1 0 0 0 0 10 21 1 0 0 0 0 11 25 1 0 0 0 0 12 14 1 0 0 0 0 12 26 2 0 0 0 0 13 16 1 0 0 0 0 13 18 1 0 0 0 0 15 14 1 1 0 0 0 15 17 1 0 0 0 0 16 22 2 0 0 0 0 17 11 1 1 0 0 0 17 19 1 0 0 0 0 18 24 1 0 0 0 0 19 9 1 6 0 0 0 19 23 1 0 0 0 0 20 8 1 6 0 0 0 20 22 1 0 0 0 0 20 23 1 0 0 0 0 21 27 2 0 0 0 0 21 28 1 0 0 0 0 22 24 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	384.2
Volume:	396.178
LogP:	0.936
LogD:	1.046
LogS:	-2.45
# Rotatable Bonds:	5
TPSA:	82.77
# H-Bond Aceptor:	6
# H-Bond Donor:	2
# Rings:	4
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.827
Synthetic Accessibility Score:	5.011
Fsp3:	0.545
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.787
MDCK Permeability:	1.1390789950382896e-05
Pgp-inhibitor:	0.001
Pgp-substrate:	0.085
Human Intestinal Absorption (HIA):	0.084
20% Bioavailability (F20%):	0.01
30% Bioavailability (F30%):	0.007

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.417
Plasma Protein Binding (PPB):	55.89900207519531%
Volume Distribution (VD):	0.647
Pgp-substrate:	31.332584381103516%

ADMET: Metabolism

CYP1A2-inhibitor:	0.051
CYP1A2-substrate:	0.405
CYP2C19-inhibitor:	0.012
CYP2C19-substrate:	0.944
CYP2C9-inhibitor:	0.004
CYP2C9-substrate:	0.859
CYP2D6-inhibitor:	0.039
CYP2D6-substrate:	0.869
CYP3A4-inhibitor:	0.006
CYP3A4-substrate:	0.817

ADMET: Excretion

Clearance (CL):	11.014
Half-life (T1/2):	0.788

ADMET: Toxicity

hERG Blockers:	0.017
Human Hepatotoxicity (H-HT):	0.759
Drug-inuced Liver Injury (DILI):	0.915
AMES Toxicity:	0.007
Rat Oral Acute Toxicity:	0.633
Maximum Recommended Daily Dose:	0.973
Skin Sensitization:	0.11
Carcinogencity:	0.535
Eye Corrosion:	0.004
Eye Irritation:	0.02
Respiratory Toxicity:	0.961

Download Data

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

Natural Product: NPC472323

Natural Product ID:	NPC472323
*Common Name:**	MWFHBQDCJDLLJP-WOMVVIRKSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	MWFHBQDCJDLLJP-WOMVVIRKSA-N
Standard InCHI:	InChI=1S/C22H28N2O4/c1-12(26)14(10-21(27)28)15-8-20-22-16(9-19(23(20)2)17(15)11-25)13-6-4-5-7-18(13)24(22)3/h4-7,14-15,17,19-20,25H,8-11H2,1-3H3,(H,27,28)/t14?,15-,17+,19-,20-/m0/s1
SMILES:	CC(=O)C(CC(=O)O)C1CC2C3=C(CC(C1CO)N2C)C4=CC=CC=C4N3C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3359055
PubChem CID:	n.a.
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000279] Alkaloids and derivatives [CHEMONTID:0003759] Macroline alkaloids

*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
NPO28762	Alstonia angustifolia	Species	Apocynaceae	Eukaryota	bark and leaf	Pahang, Malaysia	n.a.	PMID[25211145]
NPO28762	Alstonia angustifolia	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO28762	Alstonia angustifolia	Species	Apocynaceae	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

Activity Type	# Activity
Cell Line	1
NON-MOLECULAR	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT91	Cell Line	KB	Homo sapiens	IC50	>	25.0	ug.mL-1	PMID[530416]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	>	25.0	ug.mL-1	PMID[530416]

☑ 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 NPC472323 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	225
0.1-0.2	1123
0.2-0.3	5863
0.3-0.4	23282
0.4-0.5	6740
0.5-0.6	2699
0.6-0.7	2173
0.7-0.8	498
0.8-0.85	73
0.85-0.9	18
0.9-0.95	1
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9639	High Similarity	NPC15840
0.9128	High Similarity	NPC472119
0.9017	High Similarity	NPC258480
0.8857	High Similarity	NPC472107
0.8857	High Similarity	NPC79062
0.8814	High Similarity	NPC175474
0.8807	High Similarity	NPC66210
0.8793	High Similarity	NPC113626
0.8743	High Similarity	NPC143533
0.8715	High Similarity	NPC472097
0.8634	High Similarity	NPC52557
0.8626	High Similarity	NPC245916
0.8596	High Similarity	NPC478077
0.8563	High Similarity	NPC24594
0.8563	High Similarity	NPC472122
0.8556	High Similarity	NPC472112
0.8541	High Similarity	NPC79129
0.8541	High Similarity	NPC195461
0.8541	High Similarity	NPC249150
0.8541	High Similarity	NPC81654
0.8541	High Similarity	NPC313985
0.8541	High Similarity	NPC49196
0.8533	High Similarity	NPC50503
0.8514	High Similarity	NPC326575
0.8514	High Similarity	NPC234987
0.847	Intermediate Similarity	NPC289299
0.847	Intermediate Similarity	NPC57994
0.8427	Intermediate Similarity	NPC472104
0.8424	Intermediate Similarity	NPC472116
0.8418	Intermediate Similarity	NPC472105
0.8418	Intermediate Similarity	NPC187827
0.8398	Intermediate Similarity	NPC196251
0.8398	Intermediate Similarity	NPC63199
0.8398	Intermediate Similarity	NPC111602
0.8398	Intermediate Similarity	NPC102338
0.8362	Intermediate Similarity	NPC133261
0.8361	Intermediate Similarity	NPC472113
0.8324	Intermediate Similarity	NPC472110
0.8324	Intermediate Similarity	NPC472109
0.8258	Intermediate Similarity	NPC219336
0.8245	Intermediate Similarity	NPC199851
0.8245	Intermediate Similarity	NPC128265
0.8245	Intermediate Similarity	NPC294909
0.8245	Intermediate Similarity	NPC312870
0.8245	Intermediate Similarity	NPC254240
0.8239	Intermediate Similarity	NPC472123
0.8202	Intermediate Similarity	NPC217372
0.8202	Intermediate Similarity	NPC183662
0.8202	Intermediate Similarity	NPC15573
0.8125	Intermediate Similarity	NPC238457
0.8122	Intermediate Similarity	NPC139291
0.8122	Intermediate Similarity	NPC472108
0.8111	Intermediate Similarity	NPC469896
0.8108	Intermediate Similarity	NPC117244
0.8108	Intermediate Similarity	NPC473763
0.8103	Intermediate Similarity	NPC271797
0.8103	Intermediate Similarity	NPC21174
0.8092	Intermediate Similarity	NPC255229
0.8092	Intermediate Similarity	NPC81229
0.8075	Intermediate Similarity	NPC19692
0.8075	Intermediate Similarity	NPC220151
0.8068	Intermediate Similarity	NPC317430
0.8061	Intermediate Similarity	NPC472098
0.8022	Intermediate Similarity	NPC159125
0.8021	Intermediate Similarity	NPC81802
0.8021	Intermediate Similarity	NPC472295
0.8021	Intermediate Similarity	NPC247735
0.8021	Intermediate Similarity	NPC269886
0.8021	Intermediate Similarity	NPC472210
0.7989	Intermediate Similarity	NPC469938
0.7956	Intermediate Similarity	NPC248462
0.7951	Intermediate Similarity	NPC33949
0.7947	Intermediate Similarity	NPC102008
0.7943	Intermediate Similarity	NPC194881
0.791	Intermediate Similarity	NPC52254
0.7897	Intermediate Similarity	NPC53344
0.7895	Intermediate Similarity	NPC469736
0.7861	Intermediate Similarity	NPC469470
0.7861	Intermediate Similarity	NPC469501
0.7861	Intermediate Similarity	NPC329858
0.7861	Intermediate Similarity	NPC314333
0.7853	Intermediate Similarity	NPC149708
0.7839	Intermediate Similarity	NPC221100
0.7839	Intermediate Similarity	NPC234078
0.7796	Intermediate Similarity	NPC62749
0.7796	Intermediate Similarity	NPC235684
0.779	Intermediate Similarity	NPC329688
0.779	Intermediate Similarity	NPC189812
0.7789	Intermediate Similarity	NPC264176
0.7783	Intermediate Similarity	NPC472099
0.7778	Intermediate Similarity	NPC234999
0.7772	Intermediate Similarity	NPC82070
0.7772	Intermediate Similarity	NPC281049
0.7761	Intermediate Similarity	NPC476114
0.7747	Intermediate Similarity	NPC267885
0.7747	Intermediate Similarity	NPC121903
0.7692	Intermediate Similarity	NPC162730
0.7692	Intermediate Similarity	NPC203468
0.7692	Intermediate Similarity	NPC110500
0.7692	Intermediate Similarity	NPC149155
0.7688	Intermediate Similarity	NPC470003
0.7685	Intermediate Similarity	NPC174788
0.7684	Intermediate Similarity	NPC472292
0.7684	Intermediate Similarity	NPC55493
0.768	Intermediate Similarity	NPC158129
0.7673	Intermediate Similarity	NPC148183
0.7673	Intermediate Similarity	NPC152768
0.767	Intermediate Similarity	NPC475271
0.7667	Intermediate Similarity	NPC78020
0.7663	Intermediate Similarity	NPC55772
0.7663	Intermediate Similarity	NPC248041
0.7663	Intermediate Similarity	NPC283219
0.7663	Intermediate Similarity	NPC126709
0.7662	Intermediate Similarity	NPC472291
0.7656	Intermediate Similarity	NPC472293
0.7638	Intermediate Similarity	NPC469743
0.7637	Intermediate Similarity	NPC161861
0.7634	Intermediate Similarity	NPC19679
0.7629	Intermediate Similarity	NPC472297
0.7629	Intermediate Similarity	NPC472296
0.7629	Intermediate Similarity	NPC241024
0.7622	Intermediate Similarity	NPC91179
0.7612	Intermediate Similarity	NPC475778
0.7609	Intermediate Similarity	NPC145885
0.7609	Intermediate Similarity	NPC14113
0.7609	Intermediate Similarity	NPC84827
0.7606	Intermediate Similarity	NPC315555
0.7602	Intermediate Similarity	NPC476874
0.7602	Intermediate Similarity	NPC57398
0.7602	Intermediate Similarity	NPC474116
0.7571	Intermediate Similarity	NPC129721
0.7568	Intermediate Similarity	NPC213468
0.755	Intermediate Similarity	NPC478158
0.7548	Intermediate Similarity	NPC21638
0.7538	Intermediate Similarity	NPC293917
0.7526	Intermediate Similarity	NPC321708
0.7525	Intermediate Similarity	NPC75634
0.7525	Intermediate Similarity	NPC314648
0.7514	Intermediate Similarity	NPC64436
0.7514	Intermediate Similarity	NPC111275
0.7514	Intermediate Similarity	NPC56233
0.7513	Intermediate Similarity	NPC328318
0.7513	Intermediate Similarity	NPC328596
0.75	Intermediate Similarity	NPC469541
0.75	Intermediate Similarity	NPC64216
0.75	Intermediate Similarity	NPC214428
0.75	Intermediate Similarity	NPC249040
0.7487	Intermediate Similarity	NPC71037
0.7487	Intermediate Similarity	NPC472111
0.7487	Intermediate Similarity	NPC95783
0.7487	Intermediate Similarity	NPC277350
0.7475	Intermediate Similarity	NPC165599
0.7475	Intermediate Similarity	NPC476098
0.746	Intermediate Similarity	NPC62510
0.7459	Intermediate Similarity	NPC134586
0.7451	Intermediate Similarity	NPC478157
0.745	Intermediate Similarity	NPC315545
0.745	Intermediate Similarity	NPC477065
0.745	Intermediate Similarity	NPC314297
0.7448	Intermediate Similarity	NPC243716
0.7442	Intermediate Similarity	NPC20144
0.7437	Intermediate Similarity	NPC473376
0.7419	Intermediate Similarity	NPC28848
0.7419	Intermediate Similarity	NPC14325
0.7419	Intermediate Similarity	NPC211997
0.7416	Intermediate Similarity	NPC285469
0.7415	Intermediate Similarity	NPC330009
0.7415	Intermediate Similarity	NPC469928
0.7407	Intermediate Similarity	NPC228835
0.7402	Intermediate Similarity	NPC54744
0.7402	Intermediate Similarity	NPC317752
0.74	Intermediate Similarity	NPC314855
0.74	Intermediate Similarity	NPC313796
0.74	Intermediate Similarity	NPC313345
0.74	Intermediate Similarity	NPC315638
0.7398	Intermediate Similarity	NPC474916
0.7383	Intermediate Similarity	NPC473105
0.7376	Intermediate Similarity	NPC162860
0.7374	Intermediate Similarity	NPC475506
0.7366	Intermediate Similarity	NPC150048
0.7366	Intermediate Similarity	NPC313640
0.7366	Intermediate Similarity	NPC203754
0.7363	Intermediate Similarity	NPC54420
0.7363	Intermediate Similarity	NPC244741
0.7358	Intermediate Similarity	NPC129909
0.7353	Intermediate Similarity	NPC318299
0.7347	Intermediate Similarity	NPC227582
0.7344	Intermediate Similarity	NPC213629
0.734	Intermediate Similarity	NPC314834
0.7337	Intermediate Similarity	NPC155143
0.7322	Intermediate Similarity	NPC472115
0.7322	Intermediate Similarity	NPC472114
0.7322	Intermediate Similarity	NPC160105
0.7322	Intermediate Similarity	NPC49954
0.7322	Intermediate Similarity	NPC474561
0.7317	Intermediate Similarity	NPC229348
0.7316	Intermediate Similarity	NPC472294
0.7313	Intermediate Similarity	NPC475841
0.7313	Intermediate Similarity	NPC317373
0.7313	Intermediate Similarity	NPC474145

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 NPC472323 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	153
0.1-0.2	429
0.2-0.3	607
0.3-0.4	1577
0.4-0.5	2540
0.5-0.6	2684
0.6-0.7	974
0.7-0.8	171
0.8-0.85	14
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8541	High Similarity	NPD4601	Approved
0.8541	High Similarity	NPD4600	Approved
0.847	Intermediate Similarity	NPD4602	Approved
0.8351	Intermediate Similarity	NPD5721	Clinical (unspecified phase)
0.8245	Intermediate Similarity	NPD4500	Approved
0.8245	Intermediate Similarity	NPD4501	Approved
0.8138	Intermediate Similarity	NPD4397	Phase 1
0.8095	Intermediate Similarity	NPD6661	Clinical (unspecified phase)
0.8034	Intermediate Similarity	NPD750	Phase 2
0.8011	Intermediate Similarity	NPD5897	Approved
0.8011	Intermediate Similarity	NPD5899	Approved
0.8011	Intermediate Similarity	NPD5898	Approved
0.7979	Intermediate Similarity	NPD7944	Discontinued
0.7947	Intermediate Similarity	NPD53	Approved
0.7947	Intermediate Similarity	NPD7778	Approved
0.7947	Intermediate Similarity	NPD7777	Approved
0.7908	Intermediate Similarity	NPD4520	Approved
0.7861	Intermediate Similarity	NPD4499	Approved
0.7842	Intermediate Similarity	NPD7818	Clinical (unspecified phase)
0.7826	Intermediate Similarity	NPD2095	Phase 2
0.7826	Intermediate Similarity	NPD2094	Phase 2
0.7826	Intermediate Similarity	NPD2092	Phase 2
0.7826	Intermediate Similarity	NPD5728	Clinical (unspecified phase)
0.7784	Intermediate Similarity	NPD2091	Phase 2
0.7784	Intermediate Similarity	NPD2096	Phase 2
0.776	Intermediate Similarity	NPD4987	Clinical (unspecified phase)
0.7692	Intermediate Similarity	NPD482	Approved
0.7692	Intermediate Similarity	NPD4736	Clinical (unspecified phase)
0.765	Intermediate Similarity	NPD749	Clinical (unspecified phase)
0.765	Intermediate Similarity	NPD6375	Clinical (unspecified phase)
0.7634	Intermediate Similarity	NPD4345	Clinical (unspecified phase)
0.7619	Intermediate Similarity	NPD7234	Approved
0.7619	Intermediate Similarity	NPD7233	Approved
0.7619	Intermediate Similarity	NPD4334	Discontinued
0.7588	Intermediate Similarity	NPD7665	Phase 2
0.7588	Intermediate Similarity	NPD7666	Phase 3
0.7581	Intermediate Similarity	NPD4383	Clinical (unspecified phase)
0.7571	Intermediate Similarity	NPD4326	Phase 2
0.7551	Intermediate Similarity	NPD7903	Clinical (unspecified phase)
0.7541	Intermediate Similarity	NPD6183	Clinical (unspecified phase)
0.7541	Intermediate Similarity	NPD43	Approved
0.7541	Intermediate Similarity	NPD6182	Approved
0.7538	Intermediate Similarity	NPD7621	Clinical (unspecified phase)
0.7538	Intermediate Similarity	NPD7000	Clinical (unspecified phase)
0.7538	Intermediate Similarity	NPD6999	Discontinued
0.75	Intermediate Similarity	NPD1631	Approved
0.75	Intermediate Similarity	NPD6178	Phase 3
0.7487	Intermediate Similarity	NPD4901	Clinical (unspecified phase)
0.7486	Intermediate Similarity	NPD6739	Clinical (unspecified phase)
0.7474	Intermediate Similarity	NPD4948	Discontinued
0.7473	Intermediate Similarity	NPD2844	Phase 3
0.7463	Intermediate Similarity	NPD8325	Phase 3
0.7463	Intermediate Similarity	NPD8327	Clinical (unspecified phase)
0.7463	Intermediate Similarity	NPD8326	Phase 3
0.7459	Intermediate Similarity	NPD2915	Discontinued
0.7459	Intermediate Similarity	NPD5104	Approved
0.7448	Intermediate Similarity	NPD2336	Approved
0.7448	Intermediate Similarity	NPD6630	Clinical (unspecified phase)
0.7438	Intermediate Similarity	NPD7594	Clinical (unspecified phase)
0.7437	Intermediate Similarity	NPD5426	Phase 3
0.7437	Intermediate Similarity	NPD8114	Approved
0.7437	Intermediate Similarity	NPD8115	Approved
0.7437	Intermediate Similarity	NPD6987	Phase 1
0.7433	Intermediate Similarity	NPD6452	Discontinued
0.7432	Intermediate Similarity	NPD1573	Approved
0.7432	Intermediate Similarity	NPD1575	Approved
0.7426	Intermediate Similarity	NPD4900	Clinical (unspecified phase)
0.7423	Intermediate Similarity	NPD4427	Phase 2
0.7418	Intermediate Similarity	NPD4554	Clinical (unspecified phase)
0.7409	Intermediate Similarity	NPD5505	Discontinued
0.7409	Intermediate Similarity	NPD4315	Phase 2
0.74	Intermediate Similarity	NPD6732	Clinical (unspecified phase)
0.74	Intermediate Similarity	NPD7957	Phase 1
0.74	Intermediate Similarity	NPD7568	Phase 1
0.74	Intermediate Similarity	NPD7958	Clinical (unspecified phase)
0.7391	Intermediate Similarity	NPD5934	Clinical (unspecified phase)
0.7377	Intermediate Similarity	NPD4640	Approved
0.7377	Intermediate Similarity	NPD4639	Approved
0.7377	Intermediate Similarity	NPD4638	Approved
0.7358	Intermediate Similarity	NPD4918	Discontinued
0.7358	Intermediate Similarity	NPD3785	Clinical (unspecified phase)
0.7347	Intermediate Similarity	NPD5003	Discontinued
0.7345	Intermediate Similarity	NPD2882	Phase 1
0.7333	Intermediate Similarity	NPD1630	Approved
0.7327	Intermediate Similarity	NPD2916	Discontinued
0.7316	Intermediate Similarity	NPD7483	Phase 2
0.7316	Intermediate Similarity	NPD7482	Phase 2
0.7313	Intermediate Similarity	NPD7001	Phase 3
0.7304	Intermediate Similarity	NPD8013	Clinical (unspecified phase)
0.7304	Intermediate Similarity	NPD7470	Discontinued
0.73	Intermediate Similarity	NPD8072	Approved
0.7296	Intermediate Similarity	NPD2307	Discontinued
0.7293	Intermediate Similarity	NPD2511	Approved
0.729	Intermediate Similarity	NPD8372	Clinical (unspecified phase)
0.7282	Intermediate Similarity	NPD8112	Clinical (unspecified phase)
0.7278	Intermediate Similarity	NPD3385	Approved
0.7277	Intermediate Similarity	NPD5075	Discontinued
0.7273	Intermediate Similarity	NPD5501	Discontinued
0.7273	Intermediate Similarity	NPD6248	Phase 2
0.7273	Intermediate Similarity	NPD6249	Phase 2
0.7264	Intermediate Similarity	NPD5901	Discontinued
0.7264	Intermediate Similarity	NPD7712	Clinical (unspecified phase)
0.7263	Intermediate Similarity	NPD5257	Clinical (unspecified phase)
0.726	Intermediate Similarity	NPD7878	Phase 2
0.7259	Intermediate Similarity	NPD6206	Phase 1
0.7254	Intermediate Similarity	NPD6965	Clinical (unspecified phase)
0.7243	Intermediate Similarity	NPD4184	Clinical (unspecified phase)
0.7241	Intermediate Similarity	NPD4637	Clinical (unspecified phase)
0.724	Intermediate Similarity	NPD5444	Phase 1
0.7234	Intermediate Similarity	NPD6641	Approved
0.7234	Intermediate Similarity	NPD6642	Approved
0.7231	Intermediate Similarity	NPD6665	Discontinued
0.7222	Intermediate Similarity	NPD6261	Phase 3
0.7219	Intermediate Similarity	NPD5322	Clinical (unspecified phase)
0.7211	Intermediate Similarity	NPD8408	Discontinued
0.7209	Intermediate Similarity	NPD2896	Discontinued
0.7202	Intermediate Similarity	NPD2383	Phase 1
0.72	Intermediate Similarity	NPD7817	Phase 1
0.7196	Intermediate Similarity	NPD1587	Approved
0.7188	Intermediate Similarity	NPD5555	Phase 1
0.7188	Intermediate Similarity	NPD6227	Discontinued
0.7184	Intermediate Similarity	NPD5020	Approved
0.7182	Intermediate Similarity	NPD4671	Clinical (unspecified phase)
0.7182	Intermediate Similarity	NPD4669	Clinical (unspecified phase)
0.7182	Intermediate Similarity	NPD4670	Clinical (unspecified phase)
0.7181	Intermediate Similarity	NPD5471	Phase 3
0.7178	Intermediate Similarity	NPD7103	Approved
0.7178	Intermediate Similarity	NPD8272	Phase 2
0.7174	Intermediate Similarity	NPD5744	Clinical (unspecified phase)
0.7174	Intermediate Similarity	NPD4550	Clinical (unspecified phase)
0.7171	Intermediate Similarity	NPD7998	Clinical (unspecified phase)
0.7164	Intermediate Similarity	NPD8073	Approved
0.7163	Intermediate Similarity	NPD3393	Approved
0.7163	Intermediate Similarity	NPD3394	Approved
0.7163	Intermediate Similarity	NPD3389	Approved
0.7151	Intermediate Similarity	NPD6476	Clinical (unspecified phase)
0.7151	Intermediate Similarity	NPD6158	Phase 2
0.715	Intermediate Similarity	NPD8248	Clinical (unspecified phase)
0.715	Intermediate Similarity	NPD5809	Phase 3
0.7143	Intermediate Similarity	NPD4862	Clinical (unspecified phase)
0.7135	Intermediate Similarity	NPD4174	Clinical (unspecified phase)
0.7129	Intermediate Similarity	NPD8406	Clinical (unspecified phase)
0.7128	Intermediate Similarity	NPD2564	Approved
0.7128	Intermediate Similarity	NPD2565	Phase 2
0.7121	Intermediate Similarity	NPD7061	Clinical (unspecified phase)
0.712	Intermediate Similarity	NPD4399	Phase 2
0.7114	Intermediate Similarity	NPD7727	Phase 2
0.7113	Intermediate Similarity	NPD8021	Approved
0.7113	Intermediate Similarity	NPD8020	Approved
0.7108	Intermediate Similarity	NPD6838	Clinical (unspecified phase)
0.7108	Intermediate Similarity	NPD8493	Clinical (unspecified phase)
0.7101	Intermediate Similarity	NPD6657	Clinical (unspecified phase)
0.71	Intermediate Similarity	NPD3800	Clinical (unspecified phase)
0.709	Intermediate Similarity	NPD2380	Approved
0.709	Intermediate Similarity	NPD2381	Approved
0.709	Intermediate Similarity	NPD2382	Approved
0.7087	Intermediate Similarity	NPD7809	Clinical (unspecified phase)
0.7077	Intermediate Similarity	NPD1534	Approved
0.7073	Intermediate Similarity	NPD7947	Clinical (unspecified phase)
0.7072	Intermediate Similarity	NPD2809	Approved
0.7071	Intermediate Similarity	NPD7619	Phase 3
0.7071	Intermediate Similarity	NPD7618	Phase 3
0.707	Intermediate Similarity	NPD7731	Approved
0.707	Intermediate Similarity	NPD7730	Approved
0.7068	Intermediate Similarity	NPD6595	Phase 3
0.7064	Intermediate Similarity	NPD7790	Approved
0.7064	Intermediate Similarity	NPD7950	Approved
0.7064	Intermediate Similarity	NPD7791	Approved
0.7064	Intermediate Similarity	NPD7789	Approved
0.7064	Intermediate Similarity	NPD7951	Approved
0.7064	Intermediate Similarity	NPD7952	Approved
0.7064	Intermediate Similarity	NPD7953	Approved
0.7056	Intermediate Similarity	NPD7271	Approved
0.705	Intermediate Similarity	NPD6846	Clinical (unspecified phase)
0.7048	Intermediate Similarity	NPD8000	Clinical (unspecified phase)
0.7044	Intermediate Similarity	NPD5487	Phase 1
0.7043	Intermediate Similarity	NPD4643	Clinical (unspecified phase)
0.7042	Intermediate Similarity	NPD6824	Clinical (unspecified phase)
0.7042	Intermediate Similarity	NPD6995	Phase 1
0.7041	Intermediate Similarity	NPD3654	Approved
0.7041	Intermediate Similarity	NPD6281	Approved
0.7037	Intermediate Similarity	NPD1586	Approved
0.7035	Intermediate Similarity	NPD7935	Phase 2
0.7033	Intermediate Similarity	NPD4897	Phase 2
0.7022	Intermediate Similarity	NPD1683	Approved
0.7021	Intermediate Similarity	NPD5472	Clinical (unspecified phase)
0.7016	Intermediate Similarity	NPD5398	Clinical (unspecified phase)
0.7016	Intermediate Similarity	NPD4079	Approved
0.7016	Intermediate Similarity	NPD4076	Approved
0.7011	Intermediate Similarity	NPD6454	Clinical (unspecified phase)
0.701	Intermediate Similarity	NPD6610	Clinical (unspecified phase)
0.701	Intermediate Similarity	NPD6344	Clinical (unspecified phase)
0.701	Intermediate Similarity	NPD6323	Clinical (unspecified phase)
0.701	Intermediate Similarity	NPD3947	Discontinued
0.7005	Intermediate Similarity	NPD7825	Clinical (unspecified phase)
0.7005	Intermediate Similarity	NPD5021	Discontinued
0.7005	Intermediate Similarity	NPD5862	Discovery
0.7005	Intermediate Similarity	NPD7824	Approved
0.7	Intermediate Similarity	NPD7218	Clinical (unspecified phase)
0.6991	Remote Similarity	NPD7268	Clinical (unspecified phase)

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