NPASS Compound

Structure

NPC266753 OpenBabel07101719122D 23 27 0 0 1 0 0 0 0 0999 V2000 -5.2812 0.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3523 4.0404 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4093 2.1454 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3517 1.3767 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5491 -1.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4152 -1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7407 2.0456 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3776 0.9425 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 0.5878 -0.8090 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 1.2769 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1038 2.4799 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9886 0.9425 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5491 0.1910 0.0000 C 0 0 2 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 -2.6831 -0.3090 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 -0.9511 -0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4152 -0.3090 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -2.1785 3.4771 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -1.6180 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 20 1 0 0 0 0 2 21 1 0 0 0 0 3 4 1 0 0 0 0 3 13 2 0 0 0 0 4 14 2 0 0 0 0 5 6 1 0 0 0 0 5 11 1 0 0 0 0 6 20 1 0 0 0 0 7 12 2 0 0 0 0 7 13 1 0 0 0 0 8 12 1 0 0 0 0 9 11 2 0 0 0 0 9 16 1 0 0 0 0 10 22 1 0 0 0 0 10 23 1 0 0 0 0 11 17 1 0 0 0 0 12 14 1 0 0 0 0 13 21 1 0 0 0 0 14 18 1 0 0 0 0 15 8 1 6 0 0 0 15 17 1 0 0 0 0 15 20 1 0 0 0 0 16 19 2 0 0 0 0 16 22 1 0 0 0 0 17 18 2 0 0 0 0 18 19 1 0 0 0 0 19 23 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	309.14
Volume:	315.947
LogP:	3.932
LogD:	2.747
LogS:	-3.926
# Rotatable Bonds:	1
TPSA:	30.93
# H-Bond Aceptor:	4
# H-Bond Donor:	0
# Rings:	5
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.809
Synthetic Accessibility Score:	3.072
Fsp3:	0.368
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:	-4.822
MDCK Permeability:	2.9473123504430987e-05
Pgp-inhibitor:	0.396
Pgp-substrate:	0.308
Human Intestinal Absorption (HIA):	0.002
20% Bioavailability (F20%):	0.002
30% Bioavailability (F30%):	0.055

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.984
Plasma Protein Binding (PPB):	94.2652587890625%
Volume Distribution (VD):	2.826
Pgp-substrate:	2.899608850479126%

ADMET: Metabolism

CYP1A2-inhibitor:	0.902
CYP1A2-substrate:	0.919
CYP2C19-inhibitor:	0.584
CYP2C19-substrate:	0.921
CYP2C9-inhibitor:	0.045
CYP2C9-substrate:	0.78
CYP2D6-inhibitor:	0.931
CYP2D6-substrate:	0.945
CYP3A4-inhibitor:	0.783
CYP3A4-substrate:	0.875

ADMET: Excretion

Clearance (CL):	14.383
Half-life (T1/2):	0.173

ADMET: Toxicity

hERG Blockers:	0.743
Human Hepatotoxicity (H-HT):	0.284
Drug-inuced Liver Injury (DILI):	0.362
AMES Toxicity:	0.852
Rat Oral Acute Toxicity:	0.661
Maximum Recommended Daily Dose:	0.971
Skin Sensitization:	0.126
Carcinogencity:	0.79
Eye Corrosion:	0.003
Eye Irritation:	0.011
Respiratory Toxicity:	0.886

Download Data

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

Natural Product: NPC266753

Natural Product ID:	NPC266753
*Common Name:**	GXFOBPWUVXXUIF-OAHLLOKOSA-N
IUPAC Name:	n.a.
Synonyms:	(-)-Isolaureline
Standard InCHIKey:	GXFOBPWUVXXUIF-OAHLLOKOSA-N
Standard InCHI:	InChI=1S/C19H19NO3/c1-20-6-5-11-9-16-19(23-10-22-16)18-14-4-3-13(21-2)7-12(14)8-15(20)17(11)18/h3-4,7,9,15H,5-6,8,10H2,1-2H3/t15-/m1/s1
SMILES:	CN1CCc2cc3c(c4-c5ccc(cc5C[C@@H]1c24)OC)OCO3
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL510954
PubChem CID:	44584506
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
NPO22151	Stephania pierrei	Species	Menispermaceae	Eukaryota	tubers	n.a.	n.a.	PMID[8254346]
NPO22151	Stephania pierrei	Species	Menispermaceae	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
ED50	14
Others	2

Activity Type	# Activity
Cell Line	7
NON-MOLECULAR	5
Organism	2
Others	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT453	Cell Line	HT-1080	Homo sapiens	ED50	=	1.8	ug ml-1	PMID[475531]
NPT147	Cell Line	SK-MEL-2	Homo sapiens	ED50	>	20.0	ug ml-1	PMID[475531]
NPT91	Cell Line	KB	Homo sapiens	ED50	=	2.5	ug ml-1	PMID[475531]
NPT168	Cell Line	P388	Mus musculus	ED50	>	5.0	ug ml-1	PMID[475531]
NPT762	Cell Line	A-431	Homo sapiens	ED50	=	1.3	ug ml-1	PMID[475531]
NPT858	Cell Line	LNCaP	Homo sapiens	ED50	=	2.9	ug ml-1	PMID[475531]
NPT133	Cell Line	ZR-75-1	Homo sapiens	ED50	=	2.6	ug ml-1	PMID[475531]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	ED50	=	2.9	ug ml-1	PMID[475531]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	ED50	=	12.2	ug ml-1	PMID[475531]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	ED50	=	3.2	ug ml-1	PMID[475531]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	ED50	=	1.2	ug ml-1	PMID[475531]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	ED50	=	1.3	ug ml-1	PMID[475531]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	ED50	=	2560.0	ng/ml	PMID[475531]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	ED50	=	1610.0	ng/ml	PMID[475531]
NPT2	Others	Unspecified		Ratio ED50	>	1.0	n.a.	PMID[475531]
NPT2	Others	Unspecified		Ratio ED50	=	1.0	n.a.	PMID[475531]

☑ 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 NPC266753 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	389
0.1-0.2	2001
0.2-0.3	9561
0.3-0.4	8254
0.4-0.5	7789
0.5-0.6	11421
0.6-0.7	2427
0.7-0.8	559
0.8-0.85	138
0.85-0.9	100
0.9-0.95	39
0.95-1	19

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC477559
1.0	High Similarity	NPC160298
1.0	High Similarity	NPC306902
1.0	High Similarity	NPC232924
0.9803	High Similarity	NPC225774
0.9739	High Similarity	NPC219341
0.9739	High Similarity	NPC24264
0.9739	High Similarity	NPC476432
0.9675	High Similarity	NPC298979
0.9675	High Similarity	NPC247389
0.9673	High Similarity	NPC16805
0.9673	High Similarity	NPC167546
0.9673	High Similarity	NPC302527
0.9613	High Similarity	NPC241055
0.961	High Similarity	NPC304659
0.961	High Similarity	NPC86144
0.9548	High Similarity	NPC210918
0.9545	High Similarity	NPC168409
0.953	High Similarity	NPC326316
0.953	High Similarity	NPC81733
0.9481	High Similarity	NPC189470
0.9367	High Similarity	NPC19520
0.9367	High Similarity	NPC149090
0.9304	High Similarity	NPC6152
0.9255	High Similarity	NPC320223
0.9255	High Similarity	NPC114364
0.925	High Similarity	NPC199465
0.925	High Similarity	NPC229166
0.925	High Similarity	NPC128560
0.9221	High Similarity	NPC476572
0.9216	High Similarity	NPC216459
0.9216	High Similarity	NPC99659
0.9216	High Similarity	NPC325871
0.9216	High Similarity	NPC41178
0.9216	High Similarity	NPC138487
0.92	High Similarity	NPC475959
0.9198	High Similarity	NPC126284
0.9182	High Similarity	NPC152212
0.9156	High Similarity	NPC170503
0.9156	High Similarity	NPC146288
0.9156	High Similarity	NPC126519
0.9156	High Similarity	NPC203784
0.9103	High Similarity	NPC27410
0.9103	High Similarity	NPC166014
0.9091	High Similarity	NPC76079
0.9085	High Similarity	NPC248642
0.908	High Similarity	NPC267408
0.9074	High Similarity	NPC112575
0.9038	High Similarity	NPC477080
0.9032	High Similarity	NPC31311
0.9032	High Similarity	NPC234392
0.903	High Similarity	NPC156576
0.9024	High Similarity	NPC474506
0.9024	High Similarity	NPC32413
0.9018	High Similarity	NPC23219
0.9013	High Similarity	NPC219162
0.9012	High Similarity	NPC477558
0.897	High Similarity	NPC116284
0.8963	High Similarity	NPC258695
0.8963	High Similarity	NPC470879
0.8961	High Similarity	NPC210148
0.8961	High Similarity	NPC233029
0.8916	High Similarity	NPC135772
0.8909	High Similarity	NPC155442
0.8909	High Similarity	NPC179704
0.8909	High Similarity	NPC476574
0.8909	High Similarity	NPC312918
0.8909	High Similarity	NPC477561
0.8902	High Similarity	NPC294790
0.8902	High Similarity	NPC118633
0.8902	High Similarity	NPC148693
0.8882	High Similarity	NPC90844
0.8882	High Similarity	NPC95075
0.8882	High Similarity	NPC253883
0.8874	High Similarity	NPC145304
0.8869	High Similarity	NPC237579
0.8868	High Similarity	NPC324144
0.8859	High Similarity	NPC470925
0.8855	High Similarity	NPC249405
0.8846	High Similarity	NPC244112
0.8846	High Similarity	NPC93593
0.8841	High Similarity	NPC287588
0.8824	High Similarity	NPC130941
0.882	High Similarity	NPC145832
0.882	High Similarity	NPC306555
0.882	High Similarity	NPC81218
0.882	High Similarity	NPC474931
0.882	High Similarity	NPC158376
0.882	High Similarity	NPC117188
0.882	High Similarity	NPC205421
0.882	High Similarity	NPC12053
0.8812	High Similarity	NPC96603
0.8812	High Similarity	NPC306843
0.8812	High Similarity	NPC232514
0.8812	High Similarity	NPC212794
0.8812	High Similarity	NPC238530
0.8812	High Similarity	NPC13504
0.8812	High Similarity	NPC136508
0.8812	High Similarity	NPC276944
0.8812	High Similarity	NPC196447
0.8812	High Similarity	NPC253043
0.8812	High Similarity	NPC78222
0.8812	High Similarity	NPC477563
0.881	High Similarity	NPC214116
0.8792	High Similarity	NPC314682
0.8766	High Similarity	NPC92541
0.8758	High Similarity	NPC106295
0.8758	High Similarity	NPC16107
0.8758	High Similarity	NPC81247
0.8758	High Similarity	NPC35627
0.8758	High Similarity	NPC51957
0.8758	High Similarity	NPC210437
0.8758	High Similarity	NPC476144
0.8758	High Similarity	NPC476573
0.8757	High Similarity	NPC474904
0.875	High Similarity	NPC1229
0.8743	High Similarity	NPC476575
0.8733	High Similarity	NPC328750
0.8733	High Similarity	NPC188163
0.8733	High Similarity	NPC474915
0.8733	High Similarity	NPC213206
0.8718	High Similarity	NPC470924
0.8706	High Similarity	NPC82763
0.8701	High Similarity	NPC7467
0.8698	High Similarity	NPC57036
0.8679	High Similarity	NPC111485
0.8647	High Similarity	NPC476576
0.8647	High Similarity	NPC186546
0.8647	High Similarity	NPC312531
0.8645	High Similarity	NPC211296
0.8636	High Similarity	NPC144863
0.8618	High Similarity	NPC136860
0.8618	High Similarity	NPC128019
0.8618	High Similarity	NPC476567
0.8608	High Similarity	NPC78733
0.8599	High Similarity	NPC148898
0.8599	High Similarity	NPC26601
0.8598	High Similarity	NPC168753
0.8598	High Similarity	NPC118274
0.8591	High Similarity	NPC7018
0.8589	High Similarity	NPC204947
0.8545	High Similarity	NPC239775
0.8521	High Similarity	NPC275132
0.8519	High Similarity	NPC233650
0.8516	High Similarity	NPC476151
0.8512	High Similarity	NPC220961
0.8506	High Similarity	NPC185838
0.8497	Intermediate Similarity	NPC302001
0.8497	Intermediate Similarity	NPC117717
0.8494	Intermediate Similarity	NPC2314
0.8494	Intermediate Similarity	NPC66341
0.8494	Intermediate Similarity	NPC192135
0.8494	Intermediate Similarity	NPC285941
0.8494	Intermediate Similarity	NPC477020
0.8485	Intermediate Similarity	NPC26240
0.8485	Intermediate Similarity	NPC69712
0.8485	Intermediate Similarity	NPC477562
0.8466	Intermediate Similarity	NPC134858
0.8457	Intermediate Similarity	NPC24954
0.8452	Intermediate Similarity	NPC477560
0.8439	Intermediate Similarity	NPC475754
0.8438	Intermediate Similarity	NPC180756
0.8438	Intermediate Similarity	NPC186063
0.8438	Intermediate Similarity	NPC323443
0.8409	Intermediate Similarity	NPC193906
0.8409	Intermediate Similarity	NPC23080
0.8408	Intermediate Similarity	NPC103379
0.8408	Intermediate Similarity	NPC477565
0.8397	Intermediate Similarity	NPC179825
0.8397	Intermediate Similarity	NPC191376
0.8397	Intermediate Similarity	NPC321505
0.8375	Intermediate Similarity	NPC189266
0.8375	Intermediate Similarity	NPC469817
0.8375	Intermediate Similarity	NPC2413
0.8375	Intermediate Similarity	NPC204828
0.8375	Intermediate Similarity	NPC295691
0.8375	Intermediate Similarity	NPC184026
0.8375	Intermediate Similarity	NPC276588
0.8375	Intermediate Similarity	NPC207757
0.8375	Intermediate Similarity	NPC278799
0.8375	Intermediate Similarity	NPC193949
0.8375	Intermediate Similarity	NPC127674
0.8375	Intermediate Similarity	NPC249797
0.8375	Intermediate Similarity	NPC5238
0.8375	Intermediate Similarity	NPC110416
0.8375	Intermediate Similarity	NPC39701
0.8375	Intermediate Similarity	NPC172765
0.8375	Intermediate Similarity	NPC54379
0.8364	Intermediate Similarity	NPC150879
0.8364	Intermediate Similarity	NPC210140
0.8354	Intermediate Similarity	NPC223125
0.8344	Intermediate Similarity	NPC24233
0.8344	Intermediate Similarity	NPC60186
0.8344	Intermediate Similarity	NPC135538
0.8344	Intermediate Similarity	NPC147390
0.8344	Intermediate Similarity	NPC246587
0.8344	Intermediate Similarity	NPC476571
0.8344	Intermediate Similarity	NPC428
0.8333	Intermediate Similarity	NPC106786
0.8304	Intermediate Similarity	NPC233718

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 NPC266753 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	227
0.1-0.2	854
0.2-0.3	1037
0.3-0.4	1943
0.4-0.5	2730
0.5-0.6	1713
0.6-0.7	505
0.7-0.8	134
0.8-0.85	4
0.85-0.9	3
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8758	High Similarity	NPD4584	Approved
0.8733	High Similarity	NPD4664	Clinical (unspecified phase)
0.8562	High Similarity	NPD5084	Clinical (unspecified phase)
0.8333	Intermediate Similarity	NPD2420	Approved
0.8333	Intermediate Similarity	NPD2421	Approved
0.8303	Intermediate Similarity	NPD3051	Approved
0.8269	Intermediate Similarity	NPD6783	Clinical (unspecified phase)
0.8204	Intermediate Similarity	NPD4481	Phase 3
0.8187	Intermediate Similarity	NPD4017	Approved
0.8144	Intermediate Similarity	NPD2969	Approved
0.8144	Intermediate Similarity	NPD2970	Approved
0.8095	Intermediate Similarity	NPD27	Approved
0.8095	Intermediate Similarity	NPD2489	Approved
0.8072	Intermediate Similarity	NPD7201	Clinical (unspecified phase)
0.8037	Intermediate Similarity	NPD7298	Approved
0.8026	Intermediate Similarity	NPD3109	Approved
0.8026	Intermediate Similarity	NPD3110	Approved
0.7975	Intermediate Similarity	NPD5241	Discontinued
0.795	Intermediate Similarity	NPD3639	Approved
0.795	Intermediate Similarity	NPD3640	Phase 3
0.795	Intermediate Similarity	NPD3641	Approved
0.7935	Intermediate Similarity	NPD6029	Clinical (unspecified phase)
0.7935	Intermediate Similarity	NPD6028	Clinical (unspecified phase)
0.7895	Intermediate Similarity	NPD8252	Approved
0.7895	Intermediate Similarity	NPD8099	Discontinued
0.7895	Intermediate Similarity	NPD8251	Approved
0.7892	Intermediate Similarity	NPD6788	Approved
0.7882	Intermediate Similarity	NPD2898	Approved
0.7849	Intermediate Similarity	NPD8156	Discontinued
0.7844	Intermediate Similarity	NPD7831	Phase 2
0.7844	Intermediate Similarity	NPD7833	Phase 2
0.7844	Intermediate Similarity	NPD7832	Clinical (unspecified phase)
0.784	Intermediate Similarity	NPD6030	Approved
0.784	Intermediate Similarity	NPD4727	Phase 1
0.784	Intermediate Similarity	NPD6031	Approved
0.7829	Intermediate Similarity	NPD2968	Approved
0.7829	Intermediate Similarity	NPD2971	Approved
0.7829	Intermediate Similarity	NPD2669	Clinical (unspecified phase)
0.7799	Intermediate Similarity	NPD5754	Discontinued
0.7778	Intermediate Similarity	NPD5718	Phase 2
0.7758	Intermediate Similarity	NPD4772	Phase 2
0.7758	Intermediate Similarity	NPD4773	Phase 2
0.7753	Intermediate Similarity	NPD7906	Approved
0.7727	Intermediate Similarity	NPD554	Clinical (unspecified phase)
0.7727	Intermediate Similarity	NPD4577	Approved
0.7727	Intermediate Similarity	NPD4578	Approved
0.7665	Intermediate Similarity	NPD6818	Clinical (unspecified phase)
0.7627	Intermediate Similarity	NPD7312	Approved
0.7627	Intermediate Similarity	NPD7311	Approved
0.7627	Intermediate Similarity	NPD7310	Approved
0.7627	Intermediate Similarity	NPD7313	Approved
0.7613	Intermediate Similarity	NPD4475	Approved
0.7613	Intermediate Similarity	NPD4474	Approved
0.7609	Intermediate Similarity	NPD4420	Approved
0.7602	Intermediate Similarity	NPD7802	Discontinued
0.7598	Intermediate Similarity	NPD4663	Approved
0.7593	Intermediate Similarity	NPD3845	Phase 1
0.7593	Intermediate Similarity	NPD2422	Clinical (unspecified phase)
0.7588	Intermediate Similarity	NPD7400	Phase 3
0.7584	Intermediate Similarity	NPD7309	Approved
0.7584	Intermediate Similarity	NPD8053	Approved
0.7584	Intermediate Similarity	NPD8054	Approved
0.7569	Intermediate Similarity	NPD2490	Approved
0.7569	Intermediate Similarity	NPD2488	Approved
0.7558	Intermediate Similarity	NPD6071	Discontinued
0.7558	Intermediate Similarity	NPD4010	Discontinued
0.7558	Intermediate Similarity	NPD4166	Phase 2
0.7546	Intermediate Similarity	NPD3124	Discontinued
0.7532	Intermediate Similarity	NPD5752	Clinical (unspecified phase)
0.7529	Intermediate Similarity	NPD5602	Clinical (unspecified phase)
0.7515	Intermediate Similarity	NPD2563	Approved
0.7515	Intermediate Similarity	NPD2560	Approved
0.75	Intermediate Similarity	NPD6107	Approved
0.7471	Intermediate Similarity	NPD4581	Clinical (unspecified phase)
0.7468	Intermediate Similarity	NPD2492	Phase 1
0.7455	Intermediate Similarity	NPD3647	Clinical (unspecified phase)
0.7447	Intermediate Similarity	NPD5005	Approved
0.7447	Intermediate Similarity	NPD5006	Approved
0.7444	Intermediate Similarity	NPD5087	Clinical (unspecified phase)
0.7439	Intermediate Similarity	NPD7598	Phase 2
0.7435	Intermediate Similarity	NPD4859	Phase 1
0.743	Intermediate Similarity	NPD7281	Phase 3
0.743	Intermediate Similarity	NPD3534	Clinical (unspecified phase)
0.743	Intermediate Similarity	NPD5917	Clinical (unspecified phase)
0.743	Intermediate Similarity	NPD7280	Phase 3
0.7425	Intermediate Similarity	NPD7261	Clinical (unspecified phase)
0.7421	Intermediate Similarity	NPD6895	Approved
0.7421	Intermediate Similarity	NPD6896	Approved
0.7412	Intermediate Similarity	NPD5977	Approved
0.7412	Intermediate Similarity	NPD5978	Approved
0.7411	Intermediate Similarity	NPD3763	Approved
0.7394	Intermediate Similarity	NPD1754	Clinical (unspecified phase)
0.7366	Intermediate Similarity	NPD2975	Approved
0.7366	Intermediate Similarity	NPD2974	Approved
0.7366	Intermediate Similarity	NPD2973	Approved
0.7362	Intermediate Similarity	NPD6748	Discontinued
0.736	Intermediate Similarity	NPD6297	Approved
0.7353	Intermediate Similarity	NPD2978	Approved
0.7353	Intermediate Similarity	NPD2977	Approved
0.7341	Intermediate Similarity	NPD6037	Discontinued
0.7326	Intermediate Similarity	NPD5604	Discontinued
0.7325	Intermediate Similarity	NPD6812	Clinical (unspecified phase)
0.7312	Intermediate Similarity	NPD7667	Clinical (unspecified phase)
0.7305	Intermediate Similarity	NPD5976	Discontinued
0.7301	Intermediate Similarity	NPD5177	Phase 3
0.7289	Intermediate Similarity	NPD1424	Approved
0.7268	Intermediate Similarity	NPD3349	Phase 2
0.7267	Intermediate Similarity	NPD4108	Discontinued
0.7261	Intermediate Similarity	NPD5155	Approved
0.7261	Intermediate Similarity	NPD5156	Approved
0.725	Intermediate Similarity	NPD4579	Clinical (unspecified phase)
0.7249	Intermediate Similarity	NPD4580	Approved
0.7247	Intermediate Similarity	NPD5312	Approved
0.7247	Intermediate Similarity	NPD5313	Approved
0.7225	Intermediate Similarity	NPD4055	Discovery
0.7216	Intermediate Similarity	NPD6687	Approved
0.7216	Intermediate Similarity	NPD6688	Approved
0.7212	Intermediate Similarity	NPD5307	Clinical (unspecified phase)
0.7211	Intermediate Similarity	NPD3450	Approved
0.7211	Intermediate Similarity	NPD2493	Approved
0.7211	Intermediate Similarity	NPD2494	Approved
0.7211	Intermediate Similarity	NPD3452	Approved
0.7202	Intermediate Similarity	NPD1914	Approved
0.7198	Intermediate Similarity	NPD6853	Approved
0.7198	Intermediate Similarity	NPD6851	Approved
0.7197	Intermediate Similarity	NPD2606	Approved
0.7197	Intermediate Similarity	NPD2605	Approved
0.7197	Intermediate Similarity	NPD3595	Approved
0.7197	Intermediate Similarity	NPD3594	Approved
0.7194	Intermediate Similarity	NPD3816	Phase 1
0.7194	Intermediate Similarity	NPD3815	Phase 1
0.7193	Intermediate Similarity	NPD7945	Clinical (unspecified phase)
0.7182	Intermediate Similarity	NPD8453	Clinical (unspecified phase)
0.7179	Intermediate Similarity	NPD7247	Discontinued
0.7174	Intermediate Similarity	NPD7291	Discontinued
0.7161	Intermediate Similarity	NPD7258	Clinical (unspecified phase)
0.716	Intermediate Similarity	NPD1753	Discontinued
0.7158	Intermediate Similarity	NPD4107	Approved
0.7152	Intermediate Similarity	NPD3977	Clinical (unspecified phase)
0.7135	Intermediate Similarity	NPD7110	Phase 1
0.7135	Intermediate Similarity	NPD3408	Clinical (unspecified phase)
0.7135	Intermediate Similarity	NPD7109	Clinical (unspecified phase)
0.7134	Intermediate Similarity	NPD3637	Approved
0.7134	Intermediate Similarity	NPD3636	Approved
0.7134	Intermediate Similarity	NPD7045	Clinical (unspecified phase)
0.7134	Intermediate Similarity	NPD3635	Approved
0.7111	Intermediate Similarity	NPD3885	Approved
0.7108	Intermediate Similarity	NPD5160	Discontinued
0.7105	Intermediate Similarity	NPD8095	Phase 1
0.7098	Intermediate Similarity	NPD4583	Approved
0.7098	Intermediate Similarity	NPD4582	Approved
0.7097	Intermediate Similarity	NPD1669	Approved
0.7072	Intermediate Similarity	NPD6996	Clinical (unspecified phase)
0.7068	Intermediate Similarity	NPD5457	Discontinued
0.7066	Intermediate Similarity	NPD7124	Phase 2
0.7062	Intermediate Similarity	NPD6747	Phase 1
0.7048	Intermediate Similarity	NPD6331	Phase 2
0.7048	Intermediate Similarity	NPD6658	Clinical (unspecified phase)
0.7047	Intermediate Similarity	NPD4004	Approved
0.7047	Intermediate Similarity	NPD4002	Approved
0.7041	Intermediate Similarity	NPD6090	Discontinued
0.7039	Intermediate Similarity	NPD5966	Clinical (unspecified phase)
0.7031	Intermediate Similarity	NPD4482	Phase 3
0.703	Intermediate Similarity	NPD7037	Approved
0.7017	Intermediate Similarity	NPD3920	Phase 2
0.7012	Intermediate Similarity	NPD1632	Clinical (unspecified phase)
0.7011	Intermediate Similarity	NPD7090	Clinical (unspecified phase)
0.7011	Intermediate Similarity	NPD2358	Clinical (unspecified phase)
0.701	Intermediate Similarity	NPD4040	Phase 1
0.7	Intermediate Similarity	NPD6662	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD7294	Phase 1
0.7	Intermediate Similarity	NPD7427	Discontinued
0.6995	Remote Similarity	NPD3057	Approved
0.6994	Remote Similarity	NPD5720	Discontinued
0.6994	Remote Similarity	NPD7119	Phase 2
0.6989	Remote Similarity	NPD7243	Clinical (unspecified phase)
0.6988	Remote Similarity	NPD4236	Phase 3
0.6988	Remote Similarity	NPD4237	Approved
0.6982	Remote Similarity	NPD7020	Approved
0.6982	Remote Similarity	NPD7019	Approved
0.698	Remote Similarity	NPD8318	Clinical (unspecified phase)
0.697	Remote Similarity	NPD4725	Approved
0.697	Remote Similarity	NPD4721	Approved
0.697	Remote Similarity	NPD4726	Approved
0.6962	Remote Similarity	NPD7905	Discontinued
0.6957	Remote Similarity	NPD2674	Phase 3
0.6949	Remote Similarity	NPD5677	Discontinued
0.6947	Remote Similarity	NPD5582	Discontinued
0.6935	Remote Similarity	NPD7827	Phase 1
0.6931	Remote Similarity	NPD7262	Phase 1
0.6928	Remote Similarity	NPD4257	Approved
0.6928	Remote Similarity	NPD4256	Phase 2
0.6923	Remote Similarity	NPD7479	Phase 2
0.6919	Remote Similarity	NPD6523	Clinical (unspecified phase)
0.6919	Remote Similarity	NPD6618	Phase 2
0.6915	Remote Similarity	NPD6656	Clinical (unspecified phase)
0.6915	Remote Similarity	NPD7047	Phase 3
0.6914	Remote Similarity	NPD5616	Clinical (unspecified phase)
0.6911	Remote Similarity	NPD5564	Approved
0.6911	Remote Similarity	NPD7034	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