NPASS Compound

Structure

NPC469815 OpenBabel07101718182D 27 30 0 0 1 0 0 0 0 0999 V2000 -0.8660 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.3986 3.0827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0000 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -1.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.8053 2.1691 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.4041 2.9781 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 24 1 0 0 0 0 2 25 1 0 0 0 0 3 4 2 0 0 0 0 3 12 1 0 0 0 0 4 15 1 0 0 0 0 5 6 1 0 0 0 0 5 11 1 0 0 0 0 6 21 1 0 0 0 0 7 12 1 0 0 0 0 8 11 2 0 0 0 0 8 16 1 0 0 0 0 9 13 2 0 0 0 0 9 17 1 0 0 0 0 10 26 1 0 0 0 0 10 27 1 0 0 0 0 11 13 1 0 0 0 0 12 18 2 0 0 0 0 13 14 1 0 0 0 0 14 7 1 1 0 0 0 14 21 1 0 0 0 0 15 19 2 0 0 0 0 15 24 1 0 0 0 0 16 17 2 0 0 0 0 16 26 1 0 0 0 0 17 27 1 0 0 0 0 18 19 1 0 0 0 0 18 20 1 0 0 0 0 19 25 1 0 0 0 0 20 22 2 0 0 0 0 20 23 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	371.14
Volume:	365.533
LogP:	0.702
LogD:	1.729
LogS:	-2.39
# Rotatable Bonds:	5
TPSA:	86.25
# H-Bond Aceptor:	7
# H-Bond Donor:	2
# Rings:	4
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.835
Synthetic Accessibility Score:	3.057
Fsp3:	0.35
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
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:	-5.262
MDCK Permeability:	1.1049281056330074e-05
Pgp-inhibitor:	0.016
Pgp-substrate:	0.606
Human Intestinal Absorption (HIA):	0.003
20% Bioavailability (F20%):	0.006
30% Bioavailability (F30%):	0.003

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.665
Plasma Protein Binding (PPB):	71.0163803100586%
Volume Distribution (VD):	1.624
Pgp-substrate:	16.473909378051758%

ADMET: Metabolism

CYP1A2-inhibitor:	0.164
CYP1A2-substrate:	0.826
CYP2C19-inhibitor:	0.087
CYP2C19-substrate:	0.497
CYP2C9-inhibitor:	0.025
CYP2C9-substrate:	0.111
CYP2D6-inhibitor:	0.713
CYP2D6-substrate:	0.292
CYP3A4-inhibitor:	0.117
CYP3A4-substrate:	0.546

ADMET: Excretion

Clearance (CL):	5.603
Half-life (T1/2):	0.436

ADMET: Toxicity

hERG Blockers:	0.138
Human Hepatotoxicity (H-HT):	0.734
Drug-inuced Liver Injury (DILI):	0.963
AMES Toxicity:	0.013
Rat Oral Acute Toxicity:	0.734
Maximum Recommended Daily Dose:	0.966
Skin Sensitization:	0.11
Carcinogencity:	0.671
Eye Corrosion:	0.003
Eye Irritation:	0.009
Respiratory Toxicity:	0.932

Download Data

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

Natural Product: NPC469815

Natural Product ID:	NPC469815
*Common Name:**	Coryternatine B
IUPAC Name:	2,3-dimethoxy-6-[[(5S)-5,6,7,8-tetrahydro-[1,3]dioxolo[4,5-g]isoquinolin-5-yl]methyl]benzoic acid
Synonyms:
Standard InCHIKey:	KMFUNEOFNWQPNI-AWEZNQCLSA-N
Standard InCHI:	InChI=1S/C20H21NO6/c1-24-15-4-3-12(18(20(22)23)19(15)25-2)7-14-13-9-17-16(26-10-27-17)8-11(13)5-6-21-14/h3-4,8-9,14,21H,5-7,10H2,1-2H3,(H,22,23)/t14-/m0/s1
SMILES:	COC1=C(C(=C(C=C1)CC2C3=CC4=C(C=C3CCN2)OCO4)C(=O)O)OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1209535
PubChem CID:	49862537
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0002566] Isoquinolines and derivatives [CHEMONTID:0000054] Benzylisoquinolines

*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
NPO25345	Corydalis ternata	Species	Papaveraceae	Eukaryota	tubers	n.a.	n.a.	PMID[20594848]
NPO25345	Corydalis ternata	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO25345	Corydalis ternata	Species	Papaveraceae	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	4

Activity Type	# Activity
Cell Line	4

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT81	Cell Line	A549	Homo sapiens	IC50	>	30000.0	nM	PMID[558068]
NPT146	Cell Line	SK-OV-3	Homo sapiens	IC50	>	30000.0	nM	PMID[558068]
NPT147	Cell Line	SK-MEL-2	Homo sapiens	IC50	>	30000.0	nM	PMID[558068]
NPT148	Cell Line	HCT-15	Homo sapiens	IC50	=	24580.0	nM	PMID[558068]

☑ 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 NPC469815 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	272
0.1-0.2	1327
0.2-0.3	5104
0.3-0.4	12043
0.4-0.5	4694
0.5-0.6	9704
0.6-0.7	8786
0.7-0.8	721
0.8-0.85	18
0.85-0.9	24
0.9-0.95	1
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC469816
0.9828	High Similarity	NPC125924
0.9543	High Similarity	NPC226708
0.8977	High Similarity	NPC27887
0.8889	High Similarity	NPC46990
0.8859	High Similarity	NPC46744
0.8859	High Similarity	NPC14622
0.8859	High Similarity	NPC215098
0.8859	High Similarity	NPC73020
0.8859	High Similarity	NPC70290
0.8859	High Similarity	NPC124302
0.8804	High Similarity	NPC24228
0.8763	High Similarity	NPC314100
0.8763	High Similarity	NPC226652
0.8763	High Similarity	NPC120671
0.8763	High Similarity	NPC72788
0.8729	High Similarity	NPC169387
0.8729	High Similarity	NPC477259
0.867	High Similarity	NPC328700
0.867	High Similarity	NPC2173
0.867	High Similarity	NPC202771
0.867	High Similarity	NPC119818
0.8649	High Similarity	NPC477258
0.861	High Similarity	NPC207239
0.85	High Similarity	NPC121400
0.8343	Intermediate Similarity	NPC222524
0.8315	Intermediate Similarity	NPC116007
0.827	Intermediate Similarity	NPC18306
0.8247	Intermediate Similarity	NPC80472
0.8182	Intermediate Similarity	NPC208890
0.8182	Intermediate Similarity	NPC166979
0.8177	Intermediate Similarity	NPC67978
0.8177	Intermediate Similarity	NPC303581
0.8118	Intermediate Similarity	NPC83511
0.8087	Intermediate Similarity	NPC308267
0.8035	Intermediate Similarity	NPC207824
0.8035	Intermediate Similarity	NPC60538
0.8032	Intermediate Similarity	NPC57036
0.8022	Intermediate Similarity	NPC152212
0.8021	Intermediate Similarity	NPC135772
0.8	Intermediate Similarity	NPC238530
0.8	Intermediate Similarity	NPC276944
0.8	Intermediate Similarity	NPC232514
0.7977	Intermediate Similarity	NPC475959
0.7969	Intermediate Similarity	NPC33256
0.7967	Intermediate Similarity	NPC86469
0.7956	Intermediate Similarity	NPC304659
0.7956	Intermediate Similarity	NPC86144
0.7955	Intermediate Similarity	NPC477564
0.7955	Intermediate Similarity	NPC2295
0.7943	Intermediate Similarity	NPC277669
0.7943	Intermediate Similarity	NPC76213
0.7914	Intermediate Similarity	NPC474506
0.7914	Intermediate Similarity	NPC477561
0.7914	Intermediate Similarity	NPC32413
0.7914	Intermediate Similarity	NPC155442
0.7914	Intermediate Similarity	NPC476574
0.7914	Intermediate Similarity	NPC312918
0.791	Intermediate Similarity	NPC41178
0.791	Intermediate Similarity	NPC216459
0.791	Intermediate Similarity	NPC138487
0.7895	Intermediate Similarity	NPC186546
0.7895	Intermediate Similarity	NPC476576
0.7892	Intermediate Similarity	NPC477558
0.7877	Intermediate Similarity	NPC111485
0.7865	Intermediate Similarity	NPC146288
0.7861	Intermediate Similarity	NPC258695
0.7861	Intermediate Similarity	NPC470879
0.7845	Intermediate Similarity	NPC189470
0.7838	Intermediate Similarity	NPC2314
0.7831	Intermediate Similarity	NPC475981
0.7831	Intermediate Similarity	NPC474746
0.7826	Intermediate Similarity	NPC6152
0.7817	Intermediate Similarity	NPC286135
0.7814	Intermediate Similarity	NPC298979
0.7812	Intermediate Similarity	NPC63152
0.7807	Intermediate Similarity	NPC23219
0.779	Intermediate Similarity	NPC153631
0.7778	Intermediate Similarity	NPC275132
0.7778	Intermediate Similarity	NPC207971
0.7772	Intermediate Similarity	NPC117717
0.7765	Intermediate Similarity	NPC31311
0.7765	Intermediate Similarity	NPC234392
0.7754	Intermediate Similarity	NPC112575
0.7749	Intermediate Similarity	NPC230098
0.7749	Intermediate Similarity	NPC162694
0.7747	Intermediate Similarity	NPC59567
0.7739	Intermediate Similarity	NPC268077
0.7714	Intermediate Similarity	NPC476151
0.7713	Intermediate Similarity	NPC320223
0.7713	Intermediate Similarity	NPC114364
0.7708	Intermediate Similarity	NPC141440
0.7704	Intermediate Similarity	NPC71124
0.7701	Intermediate Similarity	NPC185838
0.7697	Intermediate Similarity	NPC233029
0.7697	Intermediate Similarity	NPC210148
0.7697	Intermediate Similarity	NPC223124
0.7684	Intermediate Similarity	NPC476575
0.7672	Intermediate Similarity	NPC474745
0.767	Intermediate Similarity	NPC246587
0.767	Intermediate Similarity	NPC476571
0.767	Intermediate Similarity	NPC135538
0.767	Intermediate Similarity	NPC147390
0.767	Intermediate Similarity	NPC428
0.767	Intermediate Similarity	NPC24233
0.7663	Intermediate Similarity	NPC35627
0.7663	Intermediate Similarity	NPC476573
0.7663	Intermediate Similarity	NPC81247
0.766	Intermediate Similarity	NPC35680
0.766	Intermediate Similarity	NPC241704
0.7647	Intermediate Similarity	NPC477020
0.7647	Intermediate Similarity	NPC192135
0.7647	Intermediate Similarity	NPC66341
0.7647	Intermediate Similarity	NPC4669
0.7637	Intermediate Similarity	NPC266753
0.7637	Intermediate Similarity	NPC232924
0.7637	Intermediate Similarity	NPC306902
0.7637	Intermediate Similarity	NPC160298
0.7637	Intermediate Similarity	NPC477559
0.7629	Intermediate Similarity	NPC475754
0.7627	Intermediate Similarity	NPC477565
0.7627	Intermediate Similarity	NPC103379
0.7622	Intermediate Similarity	NPC247389
0.7619	Intermediate Similarity	NPC474325
0.7614	Intermediate Similarity	NPC321505
0.7614	Intermediate Similarity	NPC179825
0.7614	Intermediate Similarity	NPC191376
0.7611	Intermediate Similarity	NPC278799
0.7611	Intermediate Similarity	NPC207757
0.7611	Intermediate Similarity	NPC276588
0.7611	Intermediate Similarity	NPC184026
0.7611	Intermediate Similarity	NPC54379
0.7611	Intermediate Similarity	NPC172765
0.7611	Intermediate Similarity	NPC110416
0.7611	Intermediate Similarity	NPC2413
0.7611	Intermediate Similarity	NPC39701
0.7611	Intermediate Similarity	NPC189266
0.7611	Intermediate Similarity	NPC469817
0.7611	Intermediate Similarity	NPC204828
0.7611	Intermediate Similarity	NPC193949
0.7611	Intermediate Similarity	NPC127674
0.7611	Intermediate Similarity	NPC249797
0.7611	Intermediate Similarity	NPC93593
0.7611	Intermediate Similarity	NPC295691
0.7611	Intermediate Similarity	NPC5238
0.7609	Intermediate Similarity	NPC39103
0.7609	Intermediate Similarity	NPC2770
0.7606	Intermediate Similarity	NPC128560
0.7606	Intermediate Similarity	NPC229166
0.7606	Intermediate Similarity	NPC199465
0.7592	Intermediate Similarity	NPC116284
0.7592	Intermediate Similarity	NPC248642
0.759	Intermediate Similarity	NPC94499
0.759	Intermediate Similarity	NPC254957
0.7584	Intermediate Similarity	NPC223125
0.7582	Intermediate Similarity	NPC106786
0.7581	Intermediate Similarity	NPC241055
0.7579	Intermediate Similarity	NPC32154
0.7579	Intermediate Similarity	NPC267408
0.7579	Intermediate Similarity	NPC474507
0.7577	Intermediate Similarity	NPC281581
0.7577	Intermediate Similarity	NPC82763
0.7576	Intermediate Similarity	NPC267414
0.7576	Intermediate Similarity	NPC5374
0.7572	Intermediate Similarity	NPC474915
0.7572	Intermediate Similarity	NPC188163
0.7572	Intermediate Similarity	NPC328750
0.7572	Intermediate Similarity	NPC213206
0.7569	Intermediate Similarity	NPC170503
0.7569	Intermediate Similarity	NPC203784
0.7569	Intermediate Similarity	NPC126519
0.7568	Intermediate Similarity	NPC24264
0.7568	Intermediate Similarity	NPC476432
0.7568	Intermediate Similarity	NPC219341
0.7566	Intermediate Similarity	NPC237044
0.7566	Intermediate Similarity	NPC474470
0.7554	Intermediate Similarity	NPC476569
0.7552	Intermediate Similarity	NPC156576
0.7543	Intermediate Similarity	NPC294249
0.7541	Intermediate Similarity	NPC97072
0.7541	Intermediate Similarity	NPC135006
0.7541	Intermediate Similarity	NPC215829
0.754	Intermediate Similarity	NPC477562
0.754	Intermediate Similarity	NPC69712
0.754	Intermediate Similarity	NPC474708
0.754	Intermediate Similarity	NPC26240
0.7526	Intermediate Similarity	NPC118633
0.7526	Intermediate Similarity	NPC294790
0.7526	Intermediate Similarity	NPC148693
0.7525	Intermediate Similarity	NPC83019
0.7514	Intermediate Similarity	NPC51957
0.7514	Intermediate Similarity	NPC302527
0.7514	Intermediate Similarity	NPC167546
0.7514	Intermediate Similarity	NPC476144
0.7514	Intermediate Similarity	NPC121275
0.7514	Intermediate Similarity	NPC106295
0.7514	Intermediate Similarity	NPC4138
0.7514	Intermediate Similarity	NPC314682
0.7514	Intermediate Similarity	NPC284183
0.7514	Intermediate Similarity	NPC225774

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 NPC469815 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	174
0.1-0.2	624
0.2-0.3	1081
0.3-0.4	1971
0.4-0.5	2565
0.5-0.6	1859
0.6-0.7	790
0.7-0.8	83
0.8-0.85	0
0.85-0.9	3
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8859	High Similarity	NPD4420	Approved
0.867	High Similarity	NPD5005	Approved
0.867	High Similarity	NPD5006	Approved
0.8043	Intermediate Similarity	NPD6297	Approved
0.7897	Intermediate Similarity	NPD5457	Discontinued
0.7872	Intermediate Similarity	NPD6853	Approved
0.7872	Intermediate Similarity	NPD6851	Approved
0.7632	Intermediate Similarity	NPD7280	Phase 3
0.7632	Intermediate Similarity	NPD7281	Phase 3
0.7624	Intermediate Similarity	NPD5978	Approved
0.7624	Intermediate Similarity	NPD5977	Approved
0.7592	Intermediate Similarity	NPD6618	Phase 2
0.7572	Intermediate Similarity	NPD4664	Clinical (unspecified phase)
0.7553	Intermediate Similarity	NPD5312	Approved
0.7553	Intermediate Similarity	NPD5313	Approved
0.7528	Intermediate Similarity	NPD3639	Approved
0.7528	Intermediate Similarity	NPD3641	Approved
0.7528	Intermediate Similarity	NPD3640	Phase 3
0.7526	Intermediate Similarity	NPD7038	Approved
0.7526	Intermediate Similarity	NPD7039	Approved
0.7524	Intermediate Similarity	NPD8155	Clinical (unspecified phase)
0.7514	Intermediate Similarity	NPD6107	Approved
0.7514	Intermediate Similarity	NPD4584	Approved
0.7488	Intermediate Similarity	NPD7930	Approved
0.7487	Intermediate Similarity	NPD5525	Clinical (unspecified phase)
0.7476	Intermediate Similarity	NPD7827	Phase 1
0.7473	Intermediate Similarity	NPD2977	Approved
0.7473	Intermediate Similarity	NPD2978	Approved
0.743	Intermediate Similarity	NPD6031	Approved
0.743	Intermediate Similarity	NPD6030	Approved
0.7424	Intermediate Similarity	NPD7667	Clinical (unspecified phase)
0.7419	Intermediate Similarity	NPD6625	Approved
0.7418	Intermediate Similarity	NPD7298	Approved
0.74	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.7394	Intermediate Similarity	NPD2898	Approved
0.7374	Intermediate Similarity	NPD3647	Clinical (unspecified phase)
0.7371	Intermediate Similarity	NPD5619	Clinical (unspecified phase)
0.7366	Intermediate Similarity	NPD4859	Phase 1
0.7363	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7363	Intermediate Similarity	NPD6385	Approved
0.7363	Intermediate Similarity	NPD6386	Approved
0.7358	Intermediate Similarity	NPD3534	Clinical (unspecified phase)
0.7353	Intermediate Similarity	NPD7607	Clinical (unspecified phase)
0.7347	Intermediate Similarity	NPD7235	Clinical (unspecified phase)
0.734	Intermediate Similarity	NPD5242	Approved
0.732	Intermediate Similarity	NPD7090	Clinical (unspecified phase)
0.7317	Intermediate Similarity	NPD6973	Clinical (unspecified phase)
0.7287	Intermediate Similarity	NPD4166	Phase 2
0.7273	Intermediate Similarity	NPD7296	Approved
0.7268	Intermediate Similarity	NPD6146	Clinical (unspecified phase)
0.7253	Intermediate Similarity	NPD3455	Phase 2
0.7245	Intermediate Similarity	NPD3863	Clinical (unspecified phase)
0.7245	Intermediate Similarity	NPD3857	Clinical (unspecified phase)
0.7214	Intermediate Similarity	NPD2974	Approved
0.7214	Intermediate Similarity	NPD2975	Approved
0.7214	Intermediate Similarity	NPD2973	Approved
0.7209	Intermediate Similarity	NPD554	Clinical (unspecified phase)
0.7206	Intermediate Similarity	NPD956	Clinical (unspecified phase)
0.7184	Intermediate Similarity	NPD7999	Approved
0.7177	Intermediate Similarity	NPD7783	Phase 2
0.7177	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7166	Intermediate Similarity	NPD8005	Clinical (unspecified phase)
0.7158	Intermediate Similarity	NPD824	Approved
0.7157	Intermediate Similarity	NPD3452	Approved
0.7157	Intermediate Similarity	NPD3450	Approved
0.7157	Intermediate Similarity	NPD2494	Approved
0.7157	Intermediate Similarity	NPD2493	Approved
0.7151	Intermediate Similarity	NPD5084	Clinical (unspecified phase)
0.715	Intermediate Similarity	NPD7584	Approved
0.7136	Intermediate Similarity	NPD2488	Approved
0.7136	Intermediate Similarity	NPD2490	Approved
0.7128	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7128	Intermediate Similarity	NPD3936	Clinical (unspecified phase)
0.7121	Intermediate Similarity	NPD7291	Discontinued
0.7116	Intermediate Similarity	NPD7907	Approved
0.7108	Intermediate Similarity	NPD6776	Approved
0.7108	Intermediate Similarity	NPD4580	Approved
0.7108	Intermediate Similarity	NPD6778	Approved
0.7108	Intermediate Similarity	NPD4107	Approved
0.7108	Intermediate Similarity	NPD6780	Approved
0.7108	Intermediate Similarity	NPD6782	Approved
0.7108	Intermediate Similarity	NPD6779	Approved
0.7108	Intermediate Similarity	NPD6781	Approved
0.7108	Intermediate Similarity	NPD6777	Approved
0.7107	Intermediate Similarity	NPD5087	Clinical (unspecified phase)
0.7105	Intermediate Similarity	NPD6232	Discontinued
0.7104	Intermediate Similarity	NPD6723	Discontinued
0.7098	Intermediate Similarity	NPD3050	Clinical (unspecified phase)
0.7094	Intermediate Similarity	NPD4668	Phase 2
0.7083	Intermediate Similarity	NPD3446	Phase 1
0.7081	Intermediate Similarity	NPD6873	Phase 2
0.7071	Intermediate Similarity	NPD4084	Clinical (unspecified phase)
0.707	Intermediate Similarity	NPD5433	Clinical (unspecified phase)
0.7065	Intermediate Similarity	NPD4017	Approved
0.7062	Intermediate Similarity	NPD1632	Clinical (unspecified phase)
0.7062	Intermediate Similarity	NPD5441	Clinical (unspecified phase)
0.7056	Intermediate Similarity	NPD8054	Approved
0.7056	Intermediate Similarity	NPD8053	Approved
0.7053	Intermediate Similarity	NPD4583	Approved
0.7053	Intermediate Similarity	NPD4582	Approved
0.705	Intermediate Similarity	NPD3808	Clinical (unspecified phase)
0.7049	Intermediate Similarity	NPD1670	Discontinued
0.7044	Intermediate Similarity	NPD5564	Approved
0.7043	Intermediate Similarity	NPD37	Approved
0.7039	Intermediate Similarity	NPD6823	Phase 2
0.7039	Intermediate Similarity	NPD3057	Approved
0.7035	Intermediate Similarity	NPD7693	Approved
0.7031	Intermediate Similarity	NPD3451	Clinical (unspecified phase)
0.7031	Intermediate Similarity	NPD4481	Phase 3
0.7027	Intermediate Similarity	NPD1337	Clinical (unspecified phase)
0.7023	Intermediate Similarity	NPD4665	Approved
0.7023	Intermediate Similarity	NPD8318	Clinical (unspecified phase)
0.7023	Intermediate Similarity	NPD4111	Phase 1
0.7021	Intermediate Similarity	NPD4581	Clinical (unspecified phase)
0.7017	Intermediate Similarity	NPD3845	Phase 1
0.7016	Intermediate Similarity	NPD5710	Approved
0.7016	Intermediate Similarity	NPD6071	Discontinued
0.7016	Intermediate Similarity	NPD4010	Discontinued
0.7016	Intermediate Similarity	NPD5711	Approved
0.701	Intermediate Similarity	NPD5071	Phase 2
0.7005	Intermediate Similarity	NPD4002	Approved
0.7005	Intermediate Similarity	NPD2968	Approved
0.7005	Intermediate Similarity	NPD7696	Phase 3
0.7005	Intermediate Similarity	NPD7698	Approved
0.7005	Intermediate Similarity	NPD4585	Approved
0.7005	Intermediate Similarity	NPD2971	Approved
0.7005	Intermediate Similarity	NPD7697	Approved
0.7005	Intermediate Similarity	NPD6997	Phase 2
0.7005	Intermediate Similarity	NPD4004	Approved
0.7	Intermediate Similarity	NPD8153	Approved
0.7	Intermediate Similarity	NPD6377	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD8152	Approved
0.7	Intermediate Similarity	NPD7201	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD5928	Phase 1
0.6995	Remote Similarity	NPD7473	Discontinued
0.699	Remote Similarity	NPD5192	Clinical (unspecified phase)
0.699	Remote Similarity	NPD4482	Phase 3
0.6989	Remote Similarity	NPD7110	Phase 1
0.6989	Remote Similarity	NPD4773	Phase 2
0.6989	Remote Similarity	NPD4772	Phase 2
0.6989	Remote Similarity	NPD7109	Clinical (unspecified phase)
0.6986	Remote Similarity	NPD7583	Approved
0.6978	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6973	Remote Similarity	NPD2649	Approved
0.6973	Remote Similarity	NPD2651	Approved
0.6971	Remote Similarity	NPD7871	Phase 2
0.6971	Remote Similarity	NPD7870	Phase 2
0.6968	Remote Similarity	NPD2563	Approved
0.6968	Remote Similarity	NPD2560	Approved
0.6966	Remote Similarity	NPD2935	Discontinued
0.6961	Remote Similarity	NPD5241	Discontinued
0.6959	Remote Similarity	NPD8251	Approved
0.6959	Remote Similarity	NPD8099	Discontinued
0.6959	Remote Similarity	NPD8252	Approved
0.6959	Remote Similarity	NPD3818	Discontinued
0.6957	Remote Similarity	NPD3448	Approved
0.6957	Remote Similarity	NPD2972	Approved
0.6957	Remote Similarity	NPD4727	Phase 1
0.6957	Remote Similarity	NPD3533	Approved
0.6957	Remote Similarity	NPD2491	Approved
0.6954	Remote Similarity	NPD8453	Clinical (unspecified phase)
0.6952	Remote Similarity	NPD7701	Phase 2
0.6952	Remote Similarity	NPD7585	Approved
0.6952	Remote Similarity	NPD6844	Discontinued
0.6948	Remote Similarity	NPD7571	Clinical (unspecified phase)
0.6947	Remote Similarity	NPD5709	Phase 3
0.6944	Remote Similarity	NPD5177	Phase 3
0.6944	Remote Similarity	NPD2899	Discontinued
0.6944	Remote Similarity	NPD3060	Approved
0.6943	Remote Similarity	NPD6894	Phase 1
0.694	Remote Similarity	NPD1424	Approved
0.6933	Remote Similarity	NPD7048	Phase 3
0.6932	Remote Similarity	NPD1933	Approved
0.6931	Remote Similarity	NPD4966	Approved
0.6931	Remote Similarity	NPD4965	Approved
0.6931	Remote Similarity	NPD4967	Phase 2
0.6927	Remote Similarity	NPD6747	Phase 1
0.6923	Remote Similarity	NPD7435	Discontinued
0.6923	Remote Similarity	NPD2422	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD6783	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD8156	Discontinued
0.6919	Remote Similarity	NPD3686	Approved
0.6919	Remote Similarity	NPD3687	Approved
0.6915	Remote Similarity	NPD6818	Clinical (unspecified phase)
0.6911	Remote Similarity	NPD4666	Phase 3
0.6897	Remote Similarity	NPD6214	Clinical (unspecified phase)
0.6897	Remote Similarity	NPD6212	Phase 3
0.6897	Remote Similarity	NPD6213	Phase 3
0.6895	Remote Similarity	NPD1307	Phase 2
0.6895	Remote Similarity	NPD1309	Phase 2
0.6893	Remote Similarity	NPD6874	Approved
0.6893	Remote Similarity	NPD2653	Approved
0.6891	Remote Similarity	NPD2970	Approved
0.6891	Remote Similarity	NPD2969	Approved
0.689	Remote Similarity	NPD4040	Phase 1
0.6884	Remote Similarity	NPD8149	Discontinued
0.6878	Remote Similarity	NPD8058	Clinical (unspecified phase)
0.6878	Remote Similarity	NPD8059	Phase 3
0.6875	Remote Similarity	NPD7922	Phase 1
0.6872	Remote Similarity	NPD5940	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