NPASS Compound

Structure

NPC196771 OpenBabel07101719512D 30 34 0 0 0 0 0 0 0 0999 V2000 0.3364 -5.5827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8005 -5.5827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8005 -1.5827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5296 -4.0827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3956 -4.5827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3956 -2.5827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0685 -4.5827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9945 -0.1045 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8005 -3.5827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5296 -3.0827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2024 -1.0827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2617 -4.0827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2617 -3.0827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2024 -4.0827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9345 -4.0827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3364 -2.5827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3364 -1.5827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2024 -3.0827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0685 -2.5827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9345 -3.0827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0685 -1.5827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4067 -0.9135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8005 -2.5827 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.3849 -1.1215 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.3364 -4.5827 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.8005 -4.5827 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.9345 -1.0827 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 -3.2127 -4.3917 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.2127 -2.7737 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 25 1 0 0 0 0 2 26 1 0 0 0 0 3 27 1 0 0 0 0 4 5 2 0 0 0 0 4 10 1 0 0 0 0 5 12 1 0 0 0 0 6 10 2 0 0 0 0 6 13 1 0 0 0 0 7 14 2 0 0 0 0 7 15 1 0 0 0 0 8 11 1 0 0 0 0 8 28 1 0 0 0 0 9 29 1 0 0 0 0 9 30 1 0 0 0 0 10 16 1 0 0 0 0 11 17 2 0 0 0 0 11 21 1 0 0 0 0 12 13 2 0 0 0 0 12 29 1 0 0 0 0 13 30 1 0 0 0 0 14 18 1 0 0 0 0 14 25 1 0 0 0 0 15 20 2 0 0 0 0 15 26 1 0 0 0 0 16 17 1 0 0 0 0 16 18 2 0 0 0 0 17 22 1 0 0 0 0 18 19 1 0 0 0 0 19 20 1 0 0 0 0 19 21 2 0 0 0 0 20 23 1 0 0 0 0 21 27 1 0 0 0 0 22 24 2 0 0 0 0 22 28 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	410.1
Volume:	392.88
LogP:	3.816
LogD:	2.858
LogS:	-4.857
# Rotatable Bonds:	4
TPSA:	92.68
# H-Bond Aceptor:	8
# H-Bond Donor:	1
# Rings:	5
# Heavy Atoms:	8

MedChem Properties

QED Drug-Likeness Score:	0.652
Synthetic Accessibility Score:	2.823
Fsp3:	0.227
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.983
MDCK Permeability:	3.274459231761284e-05
Pgp-inhibitor:	0.535
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.005
20% Bioavailability (F20%):	0.004
30% Bioavailability (F30%):	0.002

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.016
Plasma Protein Binding (PPB):	86.76805877685547%
Volume Distribution (VD):	0.67
Pgp-substrate:	5.266951084136963%

ADMET: Metabolism

CYP1A2-inhibitor:	0.607
CYP1A2-substrate:	0.928
CYP2C19-inhibitor:	0.951
CYP2C19-substrate:	0.325
CYP2C9-inhibitor:	0.782
CYP2C9-substrate:	0.917
CYP2D6-inhibitor:	0.113
CYP2D6-substrate:	0.913
CYP3A4-inhibitor:	0.48
CYP3A4-substrate:	0.281

ADMET: Excretion

Clearance (CL):	12.917
Half-life (T1/2):	0.262

ADMET: Toxicity

hERG Blockers:	0.051
Human Hepatotoxicity (H-HT):	0.073
Drug-inuced Liver Injury (DILI):	0.928
AMES Toxicity:	0.686
Rat Oral Acute Toxicity:	0.069
Maximum Recommended Daily Dose:	0.091
Skin Sensitization:	0.049
Carcinogencity:	0.929
Eye Corrosion:	0.003
Eye Irritation:	0.325
Respiratory Toxicity:	0.55

Download Data

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

Natural Product: NPC196771

Natural Product ID:	NPC196771
*Common Name:**	Justicinol
IUPAC Name:	9-(1,3-benzodioxol-5-yl)-5-hydroxy-4,6,8-trimethoxy-3H-benzo[f][2]benzofuran-1-one
Synonyms:	Justicinol
Standard InCHIKey:	HVJLXRHXIVYZJS-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C22H18O8/c1-25-14-7-15(26-2)20(23)19-18(14)16(10-4-5-12-13(6-10)30-9-29-12)17-11(21(19)27-3)8-28-22(17)24/h4-7,23H,8-9H2,1-3H3
SMILES:	COc1cc(OC)c2c(c1O)c(OC)c1c(c2c2ccc3c(c2)OCO3)C(=O)OC1
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL518690
PubChem CID:	11373226
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0001392] Lignans, neolignans and related compounds [CHEMONTID:0001610] Arylnaphthalene lignans

*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
NPO20590	Justicia patentiflora	Species	Acanthaceae	Eukaryota	n.a.	Vietnamese	n.a.	PMID[15921419]
NPO20590	Justicia patentiflora	Species	Acanthaceae	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	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT91	Cell Line	KB	Homo sapiens	IC50	=	300.0	nM	PMID[534670]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	=	360.0	nM	PMID[534670]

☑ 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 NPC196771 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	388
0.1-0.2	1765
0.2-0.3	3773
0.3-0.4	9423
0.4-0.5	8992
0.5-0.6	3595
0.6-0.7	5506
0.7-0.8	7021
0.8-0.85	2037
0.85-0.9	183
0.9-0.95	10
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
0.9693	High Similarity	NPC117911
0.9571	High Similarity	NPC174734
0.9571	High Similarity	NPC474042
0.9387	High Similarity	NPC22130
0.9387	High Similarity	NPC116838
0.9202	High Similarity	NPC474043
0.9152	High Similarity	NPC198796
0.9141	High Similarity	NPC143328
0.9085	High Similarity	NPC125713
0.908	High Similarity	NPC239113
0.908	High Similarity	NPC115123
0.9048	High Similarity	NPC311912
0.903	High Similarity	NPC474770
0.9024	High Similarity	NPC115281
0.9024	High Similarity	NPC181168
0.9024	High Similarity	NPC163527
0.9018	High Similarity	NPC234730
0.9006	High Similarity	NPC193377
0.9	High Similarity	NPC312006
0.9	High Similarity	NPC474075
0.9	High Similarity	NPC20114
0.9	High Similarity	NPC114550
0.9	High Similarity	NPC471920
0.9	High Similarity	NPC292712
0.9	High Similarity	NPC129930
0.9	High Similarity	NPC471921
0.9	High Similarity	NPC471922
0.8994	High Similarity	NPC88557
0.8963	High Similarity	NPC109765
0.8947	High Similarity	NPC184624
0.8935	High Similarity	NPC79322
0.8916	High Similarity	NPC91634
0.8916	High Similarity	NPC78944
0.8916	High Similarity	NPC268718
0.8916	High Similarity	NPC150943
0.8909	High Similarity	NPC202495
0.8909	High Similarity	NPC19600
0.8908	High Similarity	NPC208797
0.8908	High Similarity	NPC53680
0.8889	High Similarity	NPC471181
0.8889	High Similarity	NPC178737
0.8848	High Similarity	NPC473900
0.8844	High Similarity	NPC67629
0.8844	High Similarity	NPC79736
0.8841	High Similarity	NPC103197
0.8841	High Similarity	NPC30009
0.8795	High Similarity	NPC19947
0.8795	High Similarity	NPC207584
0.8795	High Similarity	NPC474990
0.8793	High Similarity	NPC35266
0.8793	High Similarity	NPC267549
0.8779	High Similarity	NPC158226
0.8779	High Similarity	NPC469506
0.8765	High Similarity	NPC471923
0.8765	High Similarity	NPC320471
0.8765	High Similarity	NPC118162
0.8765	High Similarity	NPC83049
0.8757	High Similarity	NPC116759
0.8757	High Similarity	NPC14294
0.875	High Similarity	NPC15212
0.875	High Similarity	NPC258322
0.875	High Similarity	NPC288149
0.875	High Similarity	NPC191352
0.8743	High Similarity	NPC275690
0.8743	High Similarity	NPC161609
0.8743	High Similarity	NPC45846
0.8736	High Similarity	NPC472723
0.8735	High Similarity	NPC237946
0.8735	High Similarity	NPC32373
0.8727	High Similarity	NPC273578
0.8721	High Similarity	NPC109827
0.8721	High Similarity	NPC17219
0.8721	High Similarity	NPC124470
0.872	High Similarity	NPC118332
0.872	High Similarity	NPC104353
0.8713	High Similarity	NPC473531
0.8713	High Similarity	NPC475453
0.8713	High Similarity	NPC471180
0.8708	High Similarity	NPC105591
0.8698	High Similarity	NPC76687
0.8698	High Similarity	NPC474763
0.8693	High Similarity	NPC8940
0.869	High Similarity	NPC96593
0.8683	High Similarity	NPC296044
0.8683	High Similarity	NPC167098
0.8678	High Similarity	NPC469354
0.8678	High Similarity	NPC199533
0.8678	High Similarity	NPC470454
0.8678	High Similarity	NPC469438
0.8674	High Similarity	NPC476358
0.8671	High Similarity	NPC260263
0.8663	High Similarity	NPC165979
0.8663	High Similarity	NPC99613
0.8663	High Similarity	NPC49487
0.8663	High Similarity	NPC163130
0.8663	High Similarity	NPC211309
0.8655	High Similarity	NPC472452
0.8647	High Similarity	NPC270837
0.8647	High Similarity	NPC475865
0.8639	High Similarity	NPC311740
0.8639	High Similarity	NPC295009
0.8639	High Similarity	NPC239890
0.8639	High Similarity	NPC209411
0.8639	High Similarity	NPC260640
0.8636	High Similarity	NPC470091
0.8636	High Similarity	NPC329161
0.8636	High Similarity	NPC240887
0.8636	High Similarity	NPC183843
0.8636	High Similarity	NPC212290
0.8629	High Similarity	NPC473713
0.8629	High Similarity	NPC297574
0.8621	High Similarity	NPC477881
0.8621	High Similarity	NPC316539
0.8614	High Similarity	NPC54179
0.8613	High Similarity	NPC180768
0.8613	High Similarity	NPC477572
0.8613	High Similarity	NPC52598
0.8613	High Similarity	NPC477573
0.8613	High Similarity	NPC477571
0.8606	High Similarity	NPC78505
0.8605	High Similarity	NPC234331
0.8605	High Similarity	NPC185498
0.8603	High Similarity	NPC174486
0.8598	High Similarity	NPC475722
0.8598	High Similarity	NPC24425
0.8598	High Similarity	NPC261322
0.8598	High Similarity	NPC149505
0.8596	High Similarity	NPC114120
0.8596	High Similarity	NPC167045
0.8596	High Similarity	NPC474301
0.8596	High Similarity	NPC327652
0.8596	High Similarity	NPC26386
0.8596	High Similarity	NPC326520
0.8596	High Similarity	NPC477884
0.8588	High Similarity	NPC473445
0.8588	High Similarity	NPC188217
0.8588	High Similarity	NPC265795
0.8588	High Similarity	NPC144843
0.8588	High Similarity	NPC291957
0.8588	High Similarity	NPC14030
0.8588	High Similarity	NPC42797
0.8588	High Similarity	NPC294965
0.858	High Similarity	NPC297807
0.858	High Similarity	NPC285973
0.858	High Similarity	NPC24627
0.858	High Similarity	NPC53889
0.858	High Similarity	NPC84571
0.858	High Similarity	NPC225624
0.858	High Similarity	NPC260300
0.858	High Similarity	NPC119910
0.8571	High Similarity	NPC35598
0.8571	High Similarity	NPC227906
0.8571	High Similarity	NPC139350
0.8571	High Similarity	NPC472607
0.8571	High Similarity	NPC222689
0.8571	High Similarity	NPC472860
0.8563	High Similarity	NPC223375
0.8563	High Similarity	NPC473697
0.8563	High Similarity	NPC472835
0.8563	High Similarity	NPC476642
0.8563	High Similarity	NPC475825
0.8555	High Similarity	NPC476279
0.8555	High Similarity	NPC471287
0.8554	High Similarity	NPC178574
0.8554	High Similarity	NPC65591
0.8554	High Similarity	NPC245948
0.8547	High Similarity	NPC261623
0.8547	High Similarity	NPC329119
0.8547	High Similarity	NPC20216
0.8547	High Similarity	NPC111490
0.8547	High Similarity	NPC29160
0.8547	High Similarity	NPC43065
0.8547	High Similarity	NPC170245
0.8545	High Similarity	NPC477700
0.8545	High Similarity	NPC13985
0.8545	High Similarity	NPC210642
0.8545	High Similarity	NPC32079
0.8538	High Similarity	NPC474350
0.8538	High Similarity	NPC156082
0.8538	High Similarity	NPC197168
0.8538	High Similarity	NPC291977
0.8538	High Similarity	NPC470898
0.8538	High Similarity	NPC67959
0.8538	High Similarity	NPC236132
0.8538	High Similarity	NPC470178
0.8538	High Similarity	NPC477689
0.8537	High Similarity	NPC668
0.8537	High Similarity	NPC174512
0.8537	High Similarity	NPC293757
0.8537	High Similarity	NPC216223
0.8537	High Similarity	NPC145569
0.8537	High Similarity	NPC127827
0.8537	High Similarity	NPC474965
0.8537	High Similarity	NPC477695
0.8531	High Similarity	NPC80956
0.8531	High Similarity	NPC84494
0.8531	High Similarity	NPC113446
0.8531	High Similarity	NPC245059
0.8529	High Similarity	NPC311803
0.8529	High Similarity	NPC25389

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 NPC196771 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	357
0.1-0.2	950
0.2-0.3	1787
0.3-0.4	2729
0.4-0.5	1825
0.5-0.6	955
0.6-0.7	380
0.7-0.8	138
0.8-0.85	23
0.85-0.9	6
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.897	High Similarity	NPD6234	Discontinued
0.8922	High Similarity	NPD6232	Discontinued
0.8772	High Similarity	NPD5844	Phase 1
0.8765	High Similarity	NPD7473	Discontinued
0.8735	High Similarity	NPD4966	Approved
0.8735	High Similarity	NPD4967	Phase 2
0.8735	High Similarity	NPD4965	Approved
0.8605	High Similarity	NPD7228	Approved
0.8554	High Similarity	NPD37	Approved
0.8529	High Similarity	NPD7199	Phase 2
0.8492	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.843	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.8402	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.8391	Intermediate Similarity	NPD3818	Discontinued
0.8364	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.8324	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.8293	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.8258	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.8202	Intermediate Similarity	NPD6559	Discontinued
0.8176	Intermediate Similarity	NPD1465	Phase 2
0.8176	Intermediate Similarity	NPD2801	Approved
0.8133	Intermediate Similarity	NPD2534	Approved
0.8133	Intermediate Similarity	NPD2533	Approved
0.8133	Intermediate Similarity	NPD2532	Approved
0.8101	Intermediate Similarity	NPD7240	Approved
0.8098	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.809	Intermediate Similarity	NPD7074	Phase 3
0.807	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.8034	Intermediate Similarity	NPD7054	Approved
0.8012	Intermediate Similarity	NPD1934	Approved
0.7989	Intermediate Similarity	NPD7472	Approved
0.7977	Intermediate Similarity	NPD3882	Suspended
0.7967	Intermediate Similarity	NPD7090	Clinical (unspecified phase)
0.7966	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7966	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7966	Intermediate Similarity	NPD6166	Phase 2
0.7943	Intermediate Similarity	NPD5494	Approved
0.7919	Intermediate Similarity	NPD3817	Phase 2
0.7898	Intermediate Similarity	NPD6959	Discontinued
0.7861	Intermediate Similarity	NPD7819	Suspended
0.7845	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7845	Intermediate Similarity	NPD6797	Phase 2
0.7802	Intermediate Similarity	NPD7251	Discontinued
0.7772	Intermediate Similarity	NPD7680	Approved
0.776	Intermediate Similarity	NPD7808	Phase 3
0.7755	Intermediate Similarity	NPD8151	Discontinued
0.7749	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.7727	Intermediate Similarity	NPD7075	Discontinued
0.7727	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7717	Intermediate Similarity	NPD8312	Approved
0.7717	Intermediate Similarity	NPD8313	Approved
0.7705	Intermediate Similarity	NPD7685	Pre-registration
0.7688	Intermediate Similarity	NPD4380	Phase 2
0.768	Intermediate Similarity	NPD7435	Discontinued
0.7677	Intermediate Similarity	NPD7783	Phase 2
0.7677	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7674	Intermediate Similarity	NPD1653	Approved
0.7654	Intermediate Similarity	NPD7229	Phase 3
0.7647	Intermediate Similarity	NPD1511	Approved
0.7644	Intermediate Similarity	NPD7411	Suspended
0.7637	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.763	Intermediate Similarity	NPD7458	Discontinued
0.7627	Intermediate Similarity	NPD3749	Approved
0.7622	Intermediate Similarity	NPD230	Phase 1
0.7617	Intermediate Similarity	NPD6776	Approved
0.7617	Intermediate Similarity	NPD6781	Approved
0.7617	Intermediate Similarity	NPD6782	Approved
0.7617	Intermediate Similarity	NPD6780	Approved
0.7617	Intermediate Similarity	NPD6779	Approved
0.7617	Intermediate Similarity	NPD6778	Approved
0.7617	Intermediate Similarity	NPD6777	Approved
0.7571	Intermediate Similarity	NPD7768	Phase 2
0.7569	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.756	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7558	Intermediate Similarity	NPD1512	Approved
0.7557	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7556	Intermediate Similarity	NPD5711	Approved
0.7556	Intermediate Similarity	NPD5710	Approved
0.7545	Intermediate Similarity	NPD2935	Discontinued
0.7529	Intermediate Similarity	NPD3226	Approved
0.7529	Intermediate Similarity	NPD6190	Approved
0.7515	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7514	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD1247	Approved
0.75	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD6801	Discontinued
0.7486	Intermediate Similarity	NPD919	Approved
0.7486	Intermediate Similarity	NPD6599	Discontinued
0.7471	Intermediate Similarity	NPD4628	Phase 3
0.7471	Intermediate Similarity	NPD3750	Approved
0.7462	Intermediate Similarity	NPD7870	Phase 2
0.7462	Intermediate Similarity	NPD7871	Phase 2
0.7458	Intermediate Similarity	NPD8455	Phase 2
0.745	Intermediate Similarity	NPD7874	Approved
0.745	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7442	Intermediate Similarity	NPD7390	Discontinued
0.7429	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7418	Intermediate Similarity	NPD3926	Phase 2
0.7416	Intermediate Similarity	NPD5402	Approved
0.7411	Intermediate Similarity	NPD7698	Approved
0.7411	Intermediate Similarity	NPD7696	Phase 3
0.7411	Intermediate Similarity	NPD7697	Approved
0.7399	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7399	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7391	Intermediate Similarity	NPD3751	Discontinued
0.7368	Intermediate Similarity	NPD7003	Approved
0.7363	Intermediate Similarity	NPD3787	Discontinued
0.736	Intermediate Similarity	NPD6823	Phase 2
0.7358	Intermediate Similarity	NPD6535	Approved
0.7358	Intermediate Similarity	NPD6534	Approved
0.735	Intermediate Similarity	NPD7701	Phase 2
0.7341	Intermediate Similarity	NPD6799	Approved
0.7333	Intermediate Similarity	NPD3764	Approved
0.7316	Intermediate Similarity	NPD8150	Discontinued
0.7278	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7278	Intermediate Similarity	NPD1510	Phase 2
0.7273	Intermediate Similarity	NPD5006	Approved
0.7273	Intermediate Similarity	NPD3027	Phase 3
0.7273	Intermediate Similarity	NPD5005	Approved
0.7262	Intermediate Similarity	NPD1607	Approved
0.7245	Intermediate Similarity	NPD7699	Phase 2
0.7245	Intermediate Similarity	NPD7700	Phase 2
0.7241	Intermediate Similarity	NPD7801	Approved
0.7235	Intermediate Similarity	NPD5405	Approved
0.7235	Intermediate Similarity	NPD5406	Approved
0.7235	Intermediate Similarity	NPD5408	Approved
0.7235	Intermediate Similarity	NPD5404	Approved
0.7229	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7228	Intermediate Similarity	NPD5242	Approved
0.7225	Intermediate Similarity	NPD8434	Phase 2
0.7216	Intermediate Similarity	NPD920	Approved
0.7209	Intermediate Similarity	NPD6674	Discontinued
0.7204	Intermediate Similarity	NPD7177	Discontinued
0.7193	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7193	Intermediate Similarity	NPD2346	Discontinued
0.7193	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7193	Intermediate Similarity	NPD7266	Discontinued
0.7177	Intermediate Similarity	NPD8155	Clinical (unspecified phase)
0.7176	Intermediate Similarity	NPD3748	Approved
0.7169	Intermediate Similarity	NPD5952	Clinical (unspecified phase)
0.7168	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7168	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7164	Intermediate Similarity	NPD7999	Approved
0.7157	Intermediate Similarity	NPD4420	Approved
0.7151	Intermediate Similarity	NPD1549	Phase 2
0.7143	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD943	Approved
0.7143	Intermediate Similarity	NPD1613	Approved
0.7143	Intermediate Similarity	NPD1240	Approved
0.7136	Intermediate Similarity	NPD7930	Approved
0.7135	Intermediate Similarity	NPD1551	Phase 2
0.7135	Intermediate Similarity	NPD2438	Suspended
0.7128	Intermediate Similarity	NPD6212	Phase 3
0.7128	Intermediate Similarity	NPD6213	Phase 3
0.7128	Intermediate Similarity	NPD6214	Clinical (unspecified phase)
0.7122	Intermediate Similarity	NPD7827	Phase 1
0.712	Intermediate Similarity	NPD8127	Discontinued
0.7114	Intermediate Similarity	NPD8320	Phase 1
0.7114	Intermediate Similarity	NPD8319	Approved
0.711	Intermediate Similarity	NPD2800	Approved
0.7108	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7102	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7095	Intermediate Similarity	NPD7028	Phase 2
0.7085	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7073	Intermediate Similarity	NPD1283	Approved
0.7066	Intermediate Similarity	NPD4625	Phase 3
0.7048	Intermediate Similarity	NPD9494	Approved
0.7048	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7041	Intermediate Similarity	NPD2979	Phase 3
0.7041	Intermediate Similarity	NPD4060	Phase 1
0.7035	Intermediate Similarity	NPD6100	Approved
0.7035	Intermediate Similarity	NPD2796	Approved
0.7035	Intermediate Similarity	NPD6099	Approved
0.7024	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7022	Intermediate Similarity	NPD5403	Approved
0.7011	Intermediate Similarity	NPD1243	Approved
0.7	Intermediate Similarity	NPD5953	Discontinued
0.7	Intermediate Similarity	NPD447	Suspended
0.7	Intermediate Similarity	NPD1933	Approved
0.6994	Remote Similarity	NPD2343	Clinical (unspecified phase)
0.6994	Remote Similarity	NPD3705	Approved
0.6989	Remote Similarity	NPD643	Clinical (unspecified phase)
0.6982	Remote Similarity	NPD6233	Phase 2
0.6977	Remote Similarity	NPD651	Clinical (unspecified phase)
0.6973	Remote Similarity	NPD6746	Phase 2
0.6971	Remote Similarity	NPD8166	Discontinued
0.6966	Remote Similarity	NPD6273	Approved
0.6961	Remote Similarity	NPD6386	Approved
0.6961	Remote Similarity	NPD6385	Approved
0.6951	Remote Similarity	NPD9269	Phase 2
0.694	Remote Similarity	NPD5353	Approved
0.6927	Remote Similarity	NPD7549	Discontinued
0.6923	Remote Similarity	NPD1699	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD6798	Discontinued
0.6912	Remote Similarity	NPD7211	Clinical (unspecified phase)
0.691	Remote Similarity	NPD5401	Approved
0.6905	Remote Similarity	NPD4908	Phase 1
0.6897	Remote Similarity	NPD2344	Approved
0.6895	Remote Similarity	NPD7286	Phase 2

Bioactivity similarity: Similar Natural Products in NPASS

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

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

A: chemistry similarity

B: biological targets similarity

C: networks similarity

D: cell-based bioactivity similarity

E: similarity based on clinical data