NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	644.43
Volume:	688.718
LogP:	7.699
LogD:	4.406
LogS:	-4.841
# Rotatable Bonds:	19
TPSA:	130.36
# H-Bond Aceptor:	8
# H-Bond Donor:	3
# Rings:	4
# Heavy Atoms:	8

MedChem Properties

QED Drug-Likeness Score:	0.093
Synthetic Accessibility Score:	4.987
Fsp3:	0.816
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.85
MDCK Permeability:	1.9525094103300944e-05
Pgp-inhibitor:	0.997
Pgp-substrate:	0.006
Human Intestinal Absorption (HIA):	0.052
20% Bioavailability (F20%):	0.999
30% Bioavailability (F30%):	0.99

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.514
Plasma Protein Binding (PPB):	96.96172332763672%
Volume Distribution (VD):	1.973
Pgp-substrate:	2.9068334102630615%

ADMET: Metabolism

CYP1A2-inhibitor:	0.05
CYP1A2-substrate:	0.106
CYP2C19-inhibitor:	0.516
CYP2C19-substrate:	0.092
CYP2C9-inhibitor:	0.58
CYP2C9-substrate:	0.236
CYP2D6-inhibitor:	0.094
CYP2D6-substrate:	0.016
CYP3A4-inhibitor:	0.894
CYP3A4-substrate:	0.115

ADMET: Excretion

Clearance (CL):	3.302
Half-life (T1/2):	0.04

ADMET: Toxicity

hERG Blockers:	0.889
Human Hepatotoxicity (H-HT):	0.945
Drug-inuced Liver Injury (DILI):	0.384
AMES Toxicity:	0.022
Rat Oral Acute Toxicity:	0.873
Maximum Recommended Daily Dose:	0.902
Skin Sensitization:	0.925
Carcinogencity:	0.058
Eye Corrosion:	0.003
Eye Irritation:	0.011
Respiratory Toxicity:	0.978

Download Data

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

Natural Product: NPC59907

Natural Product ID:	NPC59907
*Common Name:**	Hydrocotarnine
IUPAC Name:	4-methoxy-6-methyl-7,8-dihydro-5H-[1,3]dioxolo[4,5-g]isoquinoline
Synonyms:
Standard InCHIKey:	XXANNZJIZQTCBP-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C12H15NO3/c1-13-4-3-8-5-10-12(16-7-15-10)11(14-2)9(8)6-13/h5H,3-4,6-7H2,1-2H3/p+1
SMILES:	C[NH+]1CCc2cc3c(c(c2C1)OC)OCO3
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1606295
PubChem CID:	3646
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0002955] Tetrahydroisoquinolines

*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
NPO9498	Papaver somniferum	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15019787]
NPO9498	Papaver somniferum	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22029392]
NPO9498	Papaver somniferum	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23517479]
NPO9498	Papaver somniferum	Species	Papaveraceae	Eukaryota	Latex Exudate	n.a.	n.a.	Database[FooDB]
NPO9498	Papaver somniferum	Species	Papaveraceae	Eukaryota	Seed	n.a.	n.a.	Database[FooDB]
NPO9498	Papaver somniferum	Species	Papaveraceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO9498	Papaver somniferum	Species	Papaveraceae	Eukaryota	n.a.	n.a.		Database[FooDB]
NPO9498	Papaver somniferum	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO9498	Papaver somniferum	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO12265	Aquilaria agallochum	Species	Thymelaeaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO9498	Papaver somniferum	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO31048	Papaver sommiferum	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO9498	Papaver somniferum	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO12265	Aquilaria agallochum	Species	Thymelaeaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO7312	Aplidium multiplicatum	Species	Polyclinidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2466	Aloe microstigma	Species	Asphodelaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10176	Chrozophora prostrata	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9498	Papaver somniferum	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12265	Aquilaria agallochum	Species	Thymelaeaceae	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
AC50	2
IC50	2
Others	2
Potency	1

Activity Type	# Activity
Individual Protein	5
ORGANISM	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT110	Individual Protein	Cytochrome P450 2D6	Homo sapiens	Potency	=	3981.1	nM	PMID[568181]
NPT110	Individual Protein	Cytochrome P450 2D6	Homo sapiens	AC50	=	3981.07	nM	PMID[568181]
NPT208	Individual Protein	Cytochrome P450 1A2	Homo sapiens	AC50	=	1995.26	nM	PMID[568181]
NPT72	Individual Protein	Solute carrier organic anion transporter family member 1B3	Homo sapiens	Inhibition	=	98.91	%	PMID[568182]
NPT73	Individual Protein	Solute carrier organic anion transporter family member 1B1	Homo sapiens	Inhibition	=	77.76	%	PMID[568182]
NPT20555	ORGANISM	SARS-CoV-2	Severe acute respiratory syndrome coronavirus 2	IC50	>	20000.0	nM	PMID[568183]
NPT20555	ORGANISM	SARS-CoV-2	Severe acute respiratory syndrome coronavirus 2	IC50	>	19952.62	nM	PMID[568183]

☑ 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 NPC59907 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	313
0.1-0.2	1986
0.2-0.3	9747
0.3-0.4	8822
0.4-0.5	6442
0.5-0.6	10748
0.6-0.7	3480
0.7-0.8	980
0.8-0.85	160
0.85-0.9	16
0.9-0.95	1
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC37144
0.9209	High Similarity	NPC7018
0.891	High Similarity	NPC75958
0.8734	High Similarity	NPC19520
0.8734	High Similarity	NPC149090
0.8643	High Similarity	NPC160193
0.858	High Similarity	NPC244554
0.8562	High Similarity	NPC93593
0.8562	High Similarity	NPC216459
0.8562	High Similarity	NPC41178
0.8562	High Similarity	NPC138487
0.8535	High Similarity	NPC180306
0.8533	High Similarity	NPC475959
0.8506	High Similarity	NPC146288
0.8476	Intermediate Similarity	NPC299990
0.8476	Intermediate Similarity	NPC73492
0.8431	Intermediate Similarity	NPC148898
0.8418	Intermediate Similarity	NPC302527
0.8418	Intermediate Similarity	NPC16805
0.8418	Intermediate Similarity	NPC167546
0.8418	Intermediate Similarity	NPC225774
0.8414	Intermediate Similarity	NPC416184
0.8387	Intermediate Similarity	NPC234392
0.8387	Intermediate Similarity	NPC31311
0.8385	Intermediate Similarity	NPC65403
0.8365	Intermediate Similarity	NPC24264
0.8365	Intermediate Similarity	NPC219341
0.8365	Intermediate Similarity	NPC476432
0.8354	Intermediate Similarity	NPC470879
0.8354	Intermediate Similarity	NPC258695
0.8344	Intermediate Similarity	NPC112575
0.8333	Intermediate Similarity	NPC160692
0.8323	Intermediate Similarity	NPC78733
0.8313	Intermediate Similarity	NPC247389
0.8313	Intermediate Similarity	NPC210918
0.8312	Intermediate Similarity	NPC210148
0.8312	Intermediate Similarity	NPC233029
0.8303	Intermediate Similarity	NPC32413
0.8303	Intermediate Similarity	NPC474506
0.8302	Intermediate Similarity	NPC24465
0.8301	Intermediate Similarity	NPC223125
0.8293	Intermediate Similarity	NPC23219
0.8288	Intermediate Similarity	NPC131204
0.8288	Intermediate Similarity	NPC301050
0.8282	Intermediate Similarity	NPC187678
0.8263	Intermediate Similarity	NPC9867
0.825	Intermediate Similarity	NPC264850
0.825	Intermediate Similarity	NPC13916
0.8239	Intermediate Similarity	NPC320104
0.8228	Intermediate Similarity	NPC477559
0.8228	Intermediate Similarity	NPC160298
0.8228	Intermediate Similarity	NPC306902
0.8228	Intermediate Similarity	NPC266753
0.8228	Intermediate Similarity	NPC232924
0.8225	Intermediate Similarity	NPC281581
0.8221	Intermediate Similarity	NPC228040
0.8221	Intermediate Similarity	NPC2314
0.8212	Intermediate Similarity	NPC110337
0.8199	Intermediate Similarity	NPC474324
0.8199	Intermediate Similarity	NPC100566
0.8199	Intermediate Similarity	NPC57812
0.8194	Intermediate Similarity	NPC223124
0.8187	Intermediate Similarity	NPC232514
0.8187	Intermediate Similarity	NPC247972
0.8187	Intermediate Similarity	NPC276944
0.8187	Intermediate Similarity	NPC238530
0.8176	Intermediate Similarity	NPC473716
0.8176	Intermediate Similarity	NPC63152
0.8176	Intermediate Similarity	NPC475597
0.8148	Intermediate Similarity	NPC158148
0.8148	Intermediate Similarity	NPC475845
0.8148	Intermediate Similarity	NPC83198
0.8148	Intermediate Similarity	NPC204908
0.8148	Intermediate Similarity	NPC266176
0.8148	Intermediate Similarity	NPC290759
0.8148	Intermediate Similarity	NPC82533
0.8129	Intermediate Similarity	NPC24260
0.8121	Intermediate Similarity	NPC314682
0.8118	Intermediate Similarity	NPC82763
0.8117	Intermediate Similarity	NPC211296
0.8108	Intermediate Similarity	NPC253429
0.8107	Intermediate Similarity	NPC57036
0.8107	Intermediate Similarity	NPC214116
0.8105	Intermediate Similarity	NPC51957
0.8105	Intermediate Similarity	NPC106295
0.8105	Intermediate Similarity	NPC16107
0.8105	Intermediate Similarity	NPC476144
0.8105	Intermediate Similarity	NPC210437
0.8105	Intermediate Similarity	NPC476151
0.8101	Intermediate Similarity	NPC129603
0.8098	Intermediate Similarity	NPC6152
0.8098	Intermediate Similarity	NPC474708
0.8098	Intermediate Similarity	NPC311991
0.8092	Intermediate Similarity	NPC130926
0.8086	Intermediate Similarity	NPC181653
0.8086	Intermediate Similarity	NPC190332
0.8072	Intermediate Similarity	NPC15919
0.8072	Intermediate Similarity	NPC294790
0.8072	Intermediate Similarity	NPC118633
0.8072	Intermediate Similarity	NPC148693
0.8067	Intermediate Similarity	NPC188163
0.8067	Intermediate Similarity	NPC474915
0.8067	Intermediate Similarity	NPC213206
0.8067	Intermediate Similarity	NPC328750
0.8061	Intermediate Similarity	NPC128560
0.8061	Intermediate Similarity	NPC199465
0.8061	Intermediate Similarity	NPC229166
0.8059	Intermediate Similarity	NPC476576
0.8059	Intermediate Similarity	NPC186546
0.8052	Intermediate Similarity	NPC7467
0.805	Intermediate Similarity	NPC106786
0.805	Intermediate Similarity	NPC111485
0.805	Intermediate Similarity	NPC477080
0.8049	Intermediate Similarity	NPC317145
0.8049	Intermediate Similarity	NPC63646
0.8049	Intermediate Similarity	NPC470739
0.8049	Intermediate Similarity	NPC10908
0.8049	Intermediate Similarity	NPC227060
0.8049	Intermediate Similarity	NPC317439
0.8049	Intermediate Similarity	NPC225597
0.8049	Intermediate Similarity	NPC76682
0.8049	Intermediate Similarity	NPC477640
0.8049	Intermediate Similarity	NPC115284
0.8049	Intermediate Similarity	NPC198498
0.8049	Intermediate Similarity	NPC276890
0.8039	Intermediate Similarity	NPC473934
0.8037	Intermediate Similarity	NPC58766
0.8037	Intermediate Similarity	NPC475686
0.8025	Intermediate Similarity	NPC476002
0.8	Intermediate Similarity	NPC97072
0.8	Intermediate Similarity	NPC152680
0.8	Intermediate Similarity	NPC232386
0.8	Intermediate Similarity	NPC477565
0.8	Intermediate Similarity	NPC129518
0.8	Intermediate Similarity	NPC215829
0.8	Intermediate Similarity	NPC103379
0.8	Intermediate Similarity	NPC251580
0.8	Intermediate Similarity	NPC12424
0.8	Intermediate Similarity	NPC41376
0.8	Intermediate Similarity	NPC262641
0.8	Intermediate Similarity	NPC190783
0.7988	Intermediate Similarity	NPC474475
0.7987	Intermediate Similarity	NPC315707
0.7987	Intermediate Similarity	NPC40389
0.7987	Intermediate Similarity	NPC148014
0.7987	Intermediate Similarity	NPC65490
0.7987	Intermediate Similarity	NPC78359
0.7986	Intermediate Similarity	NPC172403
0.7975	Intermediate Similarity	NPC298979
0.7975	Intermediate Similarity	NPC204947
0.7975	Intermediate Similarity	NPC99659
0.7975	Intermediate Similarity	NPC244112
0.7975	Intermediate Similarity	NPC325871
0.7974	Intermediate Similarity	NPC145304
0.7964	Intermediate Similarity	NPC114364
0.7964	Intermediate Similarity	NPC320223
0.7963	Intermediate Similarity	NPC231198
0.7963	Intermediate Similarity	NPC168409
0.7961	Intermediate Similarity	NPC476567
0.7961	Intermediate Similarity	NPC136860
0.7961	Intermediate Similarity	NPC128019
0.7952	Intermediate Similarity	NPC304675
0.7952	Intermediate Similarity	NPC49353
0.795	Intermediate Similarity	NPC24954
0.7939	Intermediate Similarity	NPC239775
0.7927	Intermediate Similarity	NPC241055
0.7917	Intermediate Similarity	NPC126284
0.7914	Intermediate Similarity	NPC304659
0.7914	Intermediate Similarity	NPC86144
0.7904	Intermediate Similarity	NPC237044
0.7904	Intermediate Similarity	NPC293093
0.7904	Intermediate Similarity	NPC474470
0.7901	Intermediate Similarity	NPC189470
0.7901	Intermediate Similarity	NPC59567
0.7888	Intermediate Similarity	NPC249274
0.7879	Intermediate Similarity	NPC118274
0.7879	Intermediate Similarity	NPC168753
0.7875	Intermediate Similarity	NPC476572
0.7862	Intermediate Similarity	NPC76079
0.7862	Intermediate Similarity	NPC123323
0.7857	Intermediate Similarity	NPC119949
0.7857	Intermediate Similarity	NPC474325
0.7857	Intermediate Similarity	NPC185838
0.7853	Intermediate Similarity	NPC306669
0.7853	Intermediate Similarity	NPC475654
0.7844	Intermediate Similarity	NPC477558
0.784	Intermediate Similarity	NPC60186
0.7834	Intermediate Similarity	NPC274026
0.7831	Intermediate Similarity	NPC10871
0.7826	Intermediate Similarity	NPC59028
0.7826	Intermediate Similarity	NPC92191
0.7824	Intermediate Similarity	NPC248642
0.7824	Intermediate Similarity	NPC116284
0.7816	Intermediate Similarity	NPC117717
0.7812	Intermediate Similarity	NPC180756
0.7812	Intermediate Similarity	NPC323443
0.7811	Intermediate Similarity	NPC267408
0.7811	Intermediate Similarity	NPC475479
0.7811	Intermediate Similarity	NPC243454
0.7811	Intermediate Similarity	NPC474745

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 NPC59907 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	206
0.1-0.2	860
0.2-0.3	1226
0.3-0.4	2436
0.4-0.5	2459
0.5-0.6	1366
0.6-0.7	490
0.7-0.8	96
0.8-0.85	11
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8591	High Similarity	NPD1424	Approved
0.8165	Intermediate Similarity	NPD6788	Approved
0.8105	Intermediate Similarity	NPD4584	Approved
0.8067	Intermediate Similarity	NPD4664	Clinical (unspecified phase)
0.8049	Intermediate Similarity	NPD8252	Approved
0.8049	Intermediate Similarity	NPD8099	Discontinued
0.8049	Intermediate Similarity	NPD8251	Approved
0.8026	Intermediate Similarity	NPD5084	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD8156	Discontinued
0.7987	Intermediate Similarity	NPD2560	Approved
0.7987	Intermediate Similarity	NPD2563	Approved
0.7914	Intermediate Similarity	NPD6071	Discontinued
0.7898	Intermediate Similarity	NPD7261	Clinical (unspecified phase)
0.7792	Intermediate Similarity	NPD5307	Clinical (unspecified phase)
0.777	Intermediate Similarity	NPD554	Clinical (unspecified phase)
0.7765	Intermediate Similarity	NPD5005	Approved
0.7765	Intermediate Similarity	NPD5006	Approved
0.7755	Intermediate Similarity	NPD2669	Clinical (unspecified phase)
0.7742	Intermediate Similarity	NPD7124	Phase 2
0.7742	Intermediate Similarity	NPD6783	Clinical (unspecified phase)
0.7719	Intermediate Similarity	NPD8054	Approved
0.7719	Intermediate Similarity	NPD8053	Approved
0.7682	Intermediate Similarity	NPD6111	Discontinued
0.7658	Intermediate Similarity	NPD3641	Approved
0.7658	Intermediate Similarity	NPD3639	Approved
0.7658	Intermediate Similarity	NPD3640	Phase 3
0.7616	Intermediate Similarity	NPD2492	Phase 1
0.7584	Intermediate Similarity	NPD5718	Phase 2
0.7578	Intermediate Similarity	NPD4772	Phase 2
0.7578	Intermediate Similarity	NPD4773	Phase 2
0.7576	Intermediate Similarity	NPD5677	Discontinued
0.7562	Intermediate Similarity	NPD4017	Approved
0.7547	Intermediate Similarity	NPD6031	Approved
0.7547	Intermediate Similarity	NPD6030	Approved
0.7542	Intermediate Similarity	NPD4420	Approved
0.7531	Intermediate Similarity	NPD3383	Approved
0.7531	Intermediate Similarity	NPD3382	Approved
0.7531	Intermediate Similarity	NPD3384	Approved
0.7516	Intermediate Similarity	NPD6028	Clinical (unspecified phase)
0.7516	Intermediate Similarity	NPD6029	Clinical (unspecified phase)
0.7468	Intermediate Similarity	NPD5297	Approved
0.7455	Intermediate Similarity	NPD5604	Discontinued
0.7455	Intermediate Similarity	NPD4055	Discovery
0.745	Intermediate Similarity	NPD5752	Clinical (unspecified phase)
0.7448	Intermediate Similarity	NPD3705	Approved
0.7423	Intermediate Similarity	NPD7298	Approved
0.7396	Intermediate Similarity	NPD4481	Phase 3
0.7381	Intermediate Similarity	NPD3051	Approved
0.7378	Intermediate Similarity	NPD4585	Approved
0.7337	Intermediate Similarity	NPD2969	Approved
0.7337	Intermediate Similarity	NPD2970	Approved
0.7321	Intermediate Similarity	NPD6107	Approved
0.7314	Intermediate Similarity	NPD7090	Clinical (unspecified phase)
0.7294	Intermediate Similarity	NPD2898	Approved
0.7284	Intermediate Similarity	NPD4210	Discontinued
0.7278	Intermediate Similarity	NPD4166	Phase 2
0.7273	Intermediate Similarity	NPD6818	Clinical (unspecified phase)
0.7226	Intermediate Similarity	NPD6896	Approved
0.7226	Intermediate Similarity	NPD6895	Approved
0.7226	Intermediate Similarity	NPD2200	Suspended
0.7222	Intermediate Similarity	NPD5976	Discontinued
0.7215	Intermediate Similarity	NPD4237	Approved
0.7215	Intermediate Similarity	NPD4236	Phase 3
0.7215	Intermediate Similarity	NPD5177	Phase 3
0.7213	Intermediate Similarity	NPD8095	Phase 1
0.7197	Intermediate Similarity	NPD1375	Discontinued
0.7195	Intermediate Similarity	NPD4678	Approved
0.7195	Intermediate Similarity	NPD4675	Approved
0.7193	Intermediate Similarity	NPD2489	Approved
0.7193	Intermediate Similarity	NPD27	Approved
0.7184	Intermediate Similarity	NPD6996	Clinical (unspecified phase)
0.7169	Intermediate Similarity	NPD2978	Approved
0.7169	Intermediate Similarity	NPD2977	Approved
0.716	Intermediate Similarity	NPD7201	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD5090	Approved
0.7152	Intermediate Similarity	NPD1372	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD5089	Approved
0.7143	Intermediate Similarity	NPD7833	Phase 2
0.7143	Intermediate Similarity	NPD7832	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD2238	Phase 2
0.7143	Intermediate Similarity	NPD7831	Phase 2
0.7134	Intermediate Similarity	NPD4005	Discontinued
0.7126	Intermediate Similarity	NPD5977	Approved
0.7126	Intermediate Similarity	NPD5978	Approved
0.7125	Intermediate Similarity	NPD5241	Discontinued
0.7118	Intermediate Similarity	NPD7802	Discontinued
0.7099	Intermediate Similarity	NPD1754	Clinical (unspecified phase)
0.7095	Intermediate Similarity	NPD7906	Approved
0.7078	Intermediate Similarity	NPD4475	Approved
0.7078	Intermediate Similarity	NPD2674	Phase 3
0.7078	Intermediate Similarity	NPD4474	Approved
0.7076	Intermediate Similarity	NPD4010	Discontinued
0.7069	Intermediate Similarity	NPD5312	Approved
0.7069	Intermediate Similarity	NPD5313	Approved
0.7063	Intermediate Similarity	NPD7466	Approved
0.7062	Intermediate Similarity	NPD7280	Phase 3
0.7062	Intermediate Similarity	NPD7281	Phase 3
0.7062	Intermediate Similarity	NPD4577	Approved
0.7062	Intermediate Similarity	NPD4578	Approved
0.7055	Intermediate Similarity	NPD1350	Approved
0.7055	Intermediate Similarity	NPD1349	Approved
0.7055	Intermediate Similarity	NPD1351	Approved
0.7041	Intermediate Similarity	NPD7975	Clinical (unspecified phase)
0.7037	Intermediate Similarity	NPD3124	Discontinued
0.7035	Intermediate Similarity	NPD5242	Approved
0.7025	Intermediate Similarity	NPD1632	Clinical (unspecified phase)
0.7006	Intermediate Similarity	NPD7549	Discontinued
0.7	Intermediate Similarity	NPD3060	Approved
0.6978	Remote Similarity	NPD7296	Approved
0.6966	Remote Similarity	NPD2971	Approved
0.6966	Remote Similarity	NPD7313	Approved
0.6966	Remote Similarity	NPD2968	Approved
0.6966	Remote Similarity	NPD7311	Approved
0.6966	Remote Similarity	NPD7312	Approved
0.6966	Remote Similarity	NPD7310	Approved
0.6964	Remote Similarity	NPD5773	Approved
0.6964	Remote Similarity	NPD5772	Approved
0.6957	Remote Similarity	NPD5582	Discontinued
0.6951	Remote Similarity	NPD3647	Clinical (unspecified phase)
0.6946	Remote Similarity	NPD7110	Phase 1
0.6946	Remote Similarity	NPD7109	Clinical (unspecified phase)
0.6944	Remote Similarity	NPD4663	Approved
0.6943	Remote Similarity	NPD1772	Clinical (unspecified phase)
0.6936	Remote Similarity	NPD6687	Approved
0.6936	Remote Similarity	NPD6688	Approved
0.6933	Remote Similarity	NPD7837	Clinical (unspecified phase)
0.6932	Remote Similarity	NPD3885	Approved
0.6927	Remote Similarity	NPD7309	Approved
0.6923	Remote Similarity	NPD5353	Approved
0.691	Remote Similarity	NPD8453	Clinical (unspecified phase)
0.6909	Remote Similarity	NPD6662	Clinical (unspecified phase)
0.6906	Remote Similarity	NPD6842	Approved
0.6906	Remote Similarity	NPD6841	Approved
0.6906	Remote Similarity	NPD6843	Phase 3
0.6903	Remote Similarity	NPD1336	Approved
0.6903	Remote Similarity	NPD3144	Approved
0.6903	Remote Similarity	NPD3145	Approved
0.6894	Remote Similarity	NPD4162	Approved
0.6893	Remote Similarity	NPD6297	Approved
0.689	Remote Similarity	NPD4123	Phase 3
0.6887	Remote Similarity	NPD1420	Approved
0.6887	Remote Similarity	NPD1421	Approved
0.6886	Remote Similarity	NPD1337	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD3656	Approved
0.6865	Remote Similarity	NPD7667	Clinical (unspecified phase)
0.6857	Remote Similarity	NPD3489	Phase 3
0.6846	Remote Similarity	NPD2668	Approved
0.6846	Remote Similarity	NPD2667	Approved
0.6835	Remote Similarity	NPD2653	Approved
0.6828	Remote Similarity	NPD6621	Clinical (unspecified phase)
0.6821	Remote Similarity	NPD2230	Approved
0.6821	Remote Similarity	NPD2233	Approved
0.6821	Remote Similarity	NPD2232	Approved
0.6818	Remote Similarity	NPD3018	Phase 2
0.6815	Remote Similarity	NPD3109	Approved
0.6815	Remote Similarity	NPD3110	Approved
0.681	Remote Similarity	NPD2219	Phase 1
0.6807	Remote Similarity	NPD1914	Approved
0.6805	Remote Similarity	NPD37	Approved
0.6805	Remote Similarity	NPD7945	Clinical (unspecified phase)
0.679	Remote Similarity	NPD2654	Approved
0.6788	Remote Similarity	NPD7447	Phase 1
0.6786	Remote Similarity	NPD6875	Approved
0.6786	Remote Similarity	NPD6876	Approved
0.6776	Remote Similarity	NPD7235	Clinical (unspecified phase)
0.6769	Remote Similarity	NPD7827	Phase 1
0.6768	Remote Similarity	NPD2120	Phase 2
0.6761	Remote Similarity	NPD5602	Clinical (unspecified phase)
0.6757	Remote Similarity	NPD1408	Clinical (unspecified phase)
0.6753	Remote Similarity	NPD7905	Discontinued
0.675	Remote Similarity	NPD4108	Discontinued
0.6748	Remote Similarity	NPD6625	Approved
0.6748	Remote Similarity	NPD6748	Discontinued
0.6748	Remote Similarity	NPD3977	Clinical (unspecified phase)
0.6748	Remote Similarity	NPD5754	Discontinued
0.6747	Remote Similarity	NPD6090	Discontinued
0.6746	Remote Similarity	NPD6386	Approved
0.6746	Remote Similarity	NPD6385	Approved
0.674	Remote Similarity	NPD6853	Approved
0.674	Remote Similarity	NPD6851	Approved
0.6738	Remote Similarity	NPD2973	Approved
0.6738	Remote Similarity	NPD2974	Approved
0.6738	Remote Similarity	NPD2975	Approved
0.6735	Remote Similarity	NPD709	Approved
0.6728	Remote Similarity	NPD7153	Discontinued
0.6727	Remote Similarity	NPD2420	Approved
0.6727	Remote Similarity	NPD7212	Phase 2
0.6727	Remote Similarity	NPD2421	Approved
0.6727	Remote Similarity	NPD7213	Phase 3
0.6726	Remote Similarity	NPD824	Approved
0.6725	Remote Similarity	NPD2358	Clinical (unspecified phase)
0.6721	Remote Similarity	NPD3349	Phase 2
0.6711	Remote Similarity	NPD2981	Phase 2
0.671	Remote Similarity	NPD1530	Clinical (unspecified phase)
0.6708	Remote Similarity	NPD2161	Phase 2
0.6707	Remote Similarity	NPD3692	Discontinued
0.6707	Remote Similarity	NPD4727	Phase 1
0.6707	Remote Similarity	NPD2677	Approved
0.6706	Remote Similarity	NPD5720	Discontinued
0.6688	Remote Similarity	NPD4098	Discontinued

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