NPASS Compound

Structure

NPC256124 OpenBabel07101719522D 42 49 0 0 1 0 0 0 0 0999 V2000 2.3638 -3.1422 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4306 -1.5821 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2582 2.8569 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8066 -2.9630 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6978 -2.3466 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5708 -3.4365 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1688 -2.3466 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5049 -0.2219 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1857 -0.6273 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6850 -0.7745 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2033 -1.6272 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1820 -2.9355 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5404 -3.1181 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7943 -1.9168 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3526 -2.2504 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5255 0.6952 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2934 0.8572 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1474 -0.3101 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5834 -2.4834 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0276 -2.7602 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9607 -0.0181 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3110 -0.1426 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5605 -0.7515 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6444 -3.2121 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0432 -3.2758 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7863 -1.3123 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.4715 -1.6576 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.0536 -3.5474 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1609 -2.7602 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6903 0.6750 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6027 -0.0478 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4187 1.3419 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4539 -0.6578 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5617 0.8267 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5793 -0.1731 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3652 -1.2598 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 2.3462 -2.1423 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -0.8182 -4.5193 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.1359 -2.5376 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.4011 2.3417 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.1081 1.1123 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 37 1 0 0 0 0 2 39 1 0 0 0 0 3 40 1 0 0 0 0 4 6 2 0 0 0 0 4 19 1 0 0 0 0 5 7 2 0 0 0 0 5 20 1 0 0 0 0 6 28 1 0 0 0 0 7 29 1 0 0 0 0 8 10 1 0 0 0 0 8 21 1 0 0 0 0 9 11 1 0 0 0 0 9 22 1 0 0 0 0 10 36 1 0 0 0 0 11 37 1 0 0 0 0 12 19 2 0 0 0 0 12 24 1 0 0 0 0 13 20 2 0 0 0 0 13 25 1 0 0 0 0 14 19 1 0 0 0 0 15 20 1 0 0 0 0 16 21 2 0 0 0 0 16 30 1 0 0 0 0 17 22 2 0 0 0 0 17 32 1 0 0 0 0 18 23 2 0 0 0 0 18 31 1 0 0 0 0 21 23 1 0 0 0 0 22 33 1 0 0 0 0 23 26 1 0 0 0 0 24 25 1 0 0 0 0 24 28 2 0 0 0 0 25 29 2 0 0 0 0 26 14 1 6 0 0 0 26 36 1 0 0 0 0 27 15 1 1 0 0 0 27 33 1 0 0 0 0 27 37 1 0 0 0 0 28 38 1 0 0 0 0 29 39 1 0 0 0 0 30 31 2 0 0 0 0 30 41 1 0 0 0 0 31 42 1 0 0 0 0 32 34 2 0 0 0 0 32 40 1 0 0 0 0 33 35 2 0 0 0 0 34 35 1 0 0 0 0 34 41 1 0 0 0 0 35 42 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	562.25
Volume:	579.771
LogP:	6.625
LogD:	3.863
LogS:	-7.269
# Rotatable Bonds:	2
TPSA:	72.42
# H-Bond Aceptor:	7
# H-Bond Donor:	2
# Rings:	8
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.255
Synthetic Accessibility Score:	5.833
Fsp3:	0.314
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.719
MDCK Permeability:	1.739984145388007e-05
Pgp-inhibitor:	0.993
Pgp-substrate:	0.972
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.912
30% Bioavailability (F30%):	0.962

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.054
Plasma Protein Binding (PPB):	58.11567687988281%
Volume Distribution (VD):	1.089
Pgp-substrate:	18.063030242919922%

ADMET: Metabolism

CYP1A2-inhibitor:	0.116
CYP1A2-substrate:	0.951
CYP2C19-inhibitor:	0.184
CYP2C19-substrate:	0.913
CYP2C9-inhibitor:	0.048
CYP2C9-substrate:	0.535
CYP2D6-inhibitor:	0.026
CYP2D6-substrate:	0.957
CYP3A4-inhibitor:	0.086
CYP3A4-substrate:	0.944

ADMET: Excretion

Clearance (CL):	7.724
Half-life (T1/2):	0.114

ADMET: Toxicity

hERG Blockers:	0.953
Human Hepatotoxicity (H-HT):	0.046
Drug-inuced Liver Injury (DILI):	0.561
AMES Toxicity:	0.15
Rat Oral Acute Toxicity:	0.411
Maximum Recommended Daily Dose:	0.997
Skin Sensitization:	0.791
Carcinogencity:	0.042
Eye Corrosion:	0.003
Eye Irritation:	0.004
Respiratory Toxicity:	0.488

Download Data

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

Natural Product: NPC256124

Natural Product ID:	NPC256124
*Common Name:**	DOUULZLWVARYRD-SVBPBHIXSA-N
IUPAC Name:	n.a.
Synonyms:	2'-Nortiliacorinine
Standard InCHIKey:	DOUULZLWVARYRD-SVBPBHIXSA-N
Standard InCHI:	InChI=1S/C35H34N2O5/c1-37-11-9-22-17-32(40-3)34-35-33(22)27(37)15-20-5-7-29(39-2)25(13-20)24-12-19(4-6-28(24)38)14-26-23-18-31(42-35)30(41-34)16-21(23)8-10-36-26/h4-7,12-13,16-18,26-27,36,38H,8-11,14-15H2,1-3H3/t26-,27-/m0/s1
SMILES:	CN1CCc2cc(c3c4c2[C@@H]1Cc1ccc(c(-c2cc(ccc2O)C[C@H]2c5cc(c(cc5CCN2)O3)O4)c1)OC)OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2017490
PubChem CID:	14527219
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0001392] Lignans, neolignans and related compounds

*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
NPO941	Tiliacora triandra	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22418278]
NPO941	Tiliacora triandra	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
IC50	1
MIC	5

Activity Type	# Activity
Cell Line	1
Organism	5

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT171	Cell Line	MRC5	Homo sapiens	IC50	=	3.8	ug.mL-1	PMID[448455]
NPT115	Organism	Mycobacterium tuberculosis H37Ra	Mycobacterium tuberculosis H37Ra	MIC	=	3.1	ug.mL-1	PMID[448455]
NPT790	Organism	Mycobacterium tuberculosis H37Rv	Mycobacterium tuberculosis H37Rv	MIC	=	3.1	ug.mL-1	PMID[448455]
NPT790	Organism	Mycobacterium tuberculosis H37Rv	Mycobacterium tuberculosis H37Rv	MIC	=	6.2	ug.mL-1	PMID[448455]
NPT790	Organism	Mycobacterium tuberculosis H37Rv	Mycobacterium tuberculosis H37Rv	MIC	=	1.5	ug.mL-1	PMID[448455]

☑ 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 NPC256124 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	381
0.1-0.2	1896
0.2-0.3	9216
0.3-0.4	8990
0.4-0.5	5968
0.5-0.6	9678
0.6-0.7	5461
0.7-0.8	828
0.8-0.85	141
0.85-0.9	65
0.9-0.95	60
0.95-1	13

Similarity Score	Similarity Level	Natural Product ID
0.9709	High Similarity	NPC65312
0.9709	High Similarity	NPC139783
0.9655	High Similarity	NPC191132
0.9655	High Similarity	NPC60295
0.9651	High Similarity	NPC16357
0.9651	High Similarity	NPC95426
0.9651	High Similarity	NPC302245
0.9598	High Similarity	NPC175890
0.9598	High Similarity	NPC48490
0.9598	High Similarity	NPC274661
0.9598	High Similarity	NPC82457
0.9598	High Similarity	NPC11296
0.954	High Similarity	NPC275680
0.954	High Similarity	NPC22115
0.9477	High Similarity	NPC239584
0.9419	High Similarity	NPC475479
0.9419	High Similarity	NPC243454
0.9368	High Similarity	NPC167116
0.9368	High Similarity	NPC254441
0.9368	High Similarity	NPC274716
0.931	High Similarity	NPC42663
0.931	High Similarity	NPC290582
0.931	High Similarity	NPC222661
0.931	High Similarity	NPC285931
0.931	High Similarity	NPC258657
0.931	High Similarity	NPC229373
0.931	High Similarity	NPC311973
0.931	High Similarity	NPC251735
0.931	High Similarity	NPC49075
0.931	High Similarity	NPC328155
0.931	High Similarity	NPC15414
0.931	High Similarity	NPC290005
0.931	High Similarity	NPC54654
0.931	High Similarity	NPC185639
0.931	High Similarity	NPC7715
0.931	High Similarity	NPC90998
0.931	High Similarity	NPC104196
0.931	High Similarity	NPC8836
0.931	High Similarity	NPC181796
0.931	High Similarity	NPC182052
0.931	High Similarity	NPC223690
0.931	High Similarity	NPC271013
0.931	High Similarity	NPC217748
0.931	High Similarity	NPC239824
0.931	High Similarity	NPC279228
0.9266	High Similarity	NPC206900
0.9261	High Similarity	NPC212237
0.9261	High Similarity	NPC116465
0.9253	High Similarity	NPC286119
0.92	High Similarity	NPC30779
0.9186	High Similarity	NPC251580
0.9186	High Similarity	NPC12424
0.9186	High Similarity	NPC129518
0.9186	High Similarity	NPC41376
0.9162	High Similarity	NPC478093
0.9128	High Similarity	NPC63646
0.9128	High Similarity	NPC115284
0.9128	High Similarity	NPC276890
0.9128	High Similarity	NPC76682
0.9128	High Similarity	NPC227060
0.9128	High Similarity	NPC10908
0.9128	High Similarity	NPC317145
0.9128	High Similarity	NPC198498
0.9128	High Similarity	NPC317439
0.9111	High Similarity	NPC478091
0.9111	High Similarity	NPC473589
0.9111	High Similarity	NPC30182
0.9111	High Similarity	NPC478092
0.908	High Similarity	NPC293093
0.905	High Similarity	NPC281581
0.9034	High Similarity	NPC230276
0.9034	High Similarity	NPC257269
0.9027	High Similarity	NPC254581
0.8977	High Similarity	NPC40496
0.8977	High Similarity	NPC119068
0.895	High Similarity	NPC24260
0.8933	High Similarity	NPC302275
0.8908	High Similarity	NPC475215
0.8908	High Similarity	NPC108434
0.8833	High Similarity	NPC47077
0.8833	High Similarity	NPC14507
0.8779	High Similarity	NPC475393
0.8771	High Similarity	NPC73492
0.8771	High Similarity	NPC299990
0.8764	High Similarity	NPC474507
0.8696	High Similarity	NPC85381
0.8689	High Similarity	NPC41122
0.8689	High Similarity	NPC318805
0.8678	High Similarity	NPC317272
0.8678	High Similarity	NPC13916
0.8678	High Similarity	NPC256012
0.8678	High Similarity	NPC250846
0.8678	High Similarity	NPC223077
0.8678	High Similarity	NPC193853
0.8678	High Similarity	NPC264850
0.8678	High Similarity	NPC42549
0.8678	High Similarity	NPC56887
0.8678	High Similarity	NPC268503
0.8678	High Similarity	NPC240841
0.8663	High Similarity	NPC475654
0.8652	High Similarity	NPC173416
0.8652	High Similarity	NPC148709
0.8652	High Similarity	NPC476577
0.8621	High Similarity	NPC24465
0.8621	High Similarity	NPC209377
0.8602	High Similarity	NPC234318
0.858	High Similarity	NPC83198
0.858	High Similarity	NPC204908
0.8571	High Similarity	NPC249996
0.8541	High Similarity	NPC476565
0.8539	High Similarity	NPC192135
0.8539	High Similarity	NPC190783
0.8539	High Similarity	NPC66341
0.8539	High Similarity	NPC232386
0.8539	High Similarity	NPC152680
0.8539	High Similarity	NPC477020
0.8531	High Similarity	NPC109925
0.8525	High Similarity	NPC57036
0.8523	High Similarity	NPC204947
0.852	High Similarity	NPC38964
0.8508	High Similarity	NPC195538
0.8506	High Similarity	NPC79402
0.8506	High Similarity	NPC80759
0.8488	Intermediate Similarity	NPC247639
0.8488	Intermediate Similarity	NPC25084
0.8486	Intermediate Similarity	NPC473716
0.8486	Intermediate Similarity	NPC259350
0.8486	Intermediate Similarity	NPC223236
0.8486	Intermediate Similarity	NPC475597
0.8483	Intermediate Similarity	NPC239775
0.8466	Intermediate Similarity	NPC195392
0.8462	Intermediate Similarity	NPC476202
0.8448	Intermediate Similarity	NPC205255
0.8448	Intermediate Similarity	NPC271388
0.8448	Intermediate Similarity	NPC235143
0.8448	Intermediate Similarity	NPC119649
0.8448	Intermediate Similarity	NPC230956
0.8427	Intermediate Similarity	NPC118274
0.8427	Intermediate Similarity	NPC69712
0.8427	Intermediate Similarity	NPC26240
0.8427	Intermediate Similarity	NPC477562
0.8427	Intermediate Similarity	NPC168753
0.8409	Intermediate Similarity	NPC121275
0.8409	Intermediate Similarity	NPC4138
0.8409	Intermediate Similarity	NPC284183
0.8391	Intermediate Similarity	NPC7393
0.8391	Intermediate Similarity	NPC221864
0.8387	Intermediate Similarity	NPC475754
0.8378	Intermediate Similarity	NPC186546
0.8378	Intermediate Similarity	NPC476576
0.8342	Intermediate Similarity	NPC82056
0.8333	Intermediate Similarity	NPC79328
0.8315	Intermediate Similarity	NPC306555
0.8315	Intermediate Similarity	NPC145832
0.8315	Intermediate Similarity	NPC474931
0.8315	Intermediate Similarity	NPC81218
0.8315	Intermediate Similarity	NPC158376
0.8315	Intermediate Similarity	NPC12053
0.8315	Intermediate Similarity	NPC117188
0.8315	Intermediate Similarity	NPC205421
0.8306	Intermediate Similarity	NPC32413
0.8306	Intermediate Similarity	NPC474506
0.8295	Intermediate Similarity	NPC60186
0.8278	Intermediate Similarity	NPC10871
0.8276	Intermediate Similarity	NPC29647
0.8258	Intermediate Similarity	NPC81247
0.8258	Intermediate Similarity	NPC476573
0.8258	Intermediate Similarity	NPC35627
0.8251	Intermediate Similarity	NPC470879
0.8251	Intermediate Similarity	NPC258695
0.8242	Intermediate Similarity	NPC241704
0.8218	Intermediate Similarity	NPC189266
0.8218	Intermediate Similarity	NPC54379
0.8218	Intermediate Similarity	NPC2413
0.8218	Intermediate Similarity	NPC187022
0.8218	Intermediate Similarity	NPC207757
0.8218	Intermediate Similarity	NPC204828
0.8218	Intermediate Similarity	NPC193949
0.8218	Intermediate Similarity	NPC249797
0.8218	Intermediate Similarity	NPC184026
0.8218	Intermediate Similarity	NPC295691
0.8218	Intermediate Similarity	NPC469817
0.8218	Intermediate Similarity	NPC123323
0.8218	Intermediate Similarity	NPC110416
0.8218	Intermediate Similarity	NPC80129
0.8218	Intermediate Similarity	NPC276588
0.8218	Intermediate Similarity	NPC278799
0.8218	Intermediate Similarity	NPC5238
0.8218	Intermediate Similarity	NPC127674
0.8218	Intermediate Similarity	NPC39701
0.8218	Intermediate Similarity	NPC172765
0.8216	Intermediate Similarity	NPC135772
0.8202	Intermediate Similarity	NPC96603
0.8202	Intermediate Similarity	NPC13504
0.8202	Intermediate Similarity	NPC136508
0.8202	Intermediate Similarity	NPC477563
0.8202	Intermediate Similarity	NPC78222
0.8202	Intermediate Similarity	NPC253043
0.8202	Intermediate Similarity	NPC196447
0.8202	Intermediate Similarity	NPC306843

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 NPC256124 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	753
0.2-0.3	1175
0.3-0.4	2145
0.4-0.5	2525
0.5-0.6	1557
0.6-0.7	661
0.7-0.8	119
0.8-0.85	2
0.85-0.9	1
0.9-0.95	6
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.931	High Similarity	NPD8053	Approved
0.931	High Similarity	NPD8054	Approved
0.9128	High Similarity	NPD8099	Discontinued
0.9128	High Similarity	NPD8251	Approved
0.9128	High Similarity	NPD8252	Approved
0.9075	High Similarity	NPD8156	Discontinued
0.8977	High Similarity	NPD8453	Clinical (unspecified phase)
0.822	Intermediate Similarity	NPD8095	Phase 1
0.8218	Intermediate Similarity	NPD7298	Approved
0.8023	Intermediate Similarity	NPD4584	Approved
0.7978	Intermediate Similarity	NPD6788	Approved
0.7842	Intermediate Similarity	NPD7906	Approved
0.7816	Intermediate Similarity	NPD1424	Approved
0.7778	Intermediate Similarity	NPD4581	Clinical (unspecified phase)
0.7765	Intermediate Similarity	NPD6818	Clinical (unspecified phase)
0.7753	Intermediate Similarity	NPD4772	Phase 2
0.7753	Intermediate Similarity	NPD4773	Phase 2
0.7735	Intermediate Similarity	NPD7832	Clinical (unspecified phase)
0.7735	Intermediate Similarity	NPD7831	Phase 2
0.7735	Intermediate Similarity	NPD7833	Phase 2
0.7727	Intermediate Similarity	NPD6030	Approved
0.7727	Intermediate Similarity	NPD6031	Approved
0.7701	Intermediate Similarity	NPD3845	Phase 1
0.7692	Intermediate Similarity	NPD7667	Clinical (unspecified phase)
0.7674	Intermediate Similarity	NPD4664	Clinical (unspecified phase)
0.7663	Intermediate Similarity	NPD6071	Discontinued
0.7657	Intermediate Similarity	NPD7598	Phase 2
0.7632	Intermediate Similarity	NPD7312	Approved
0.7632	Intermediate Similarity	NPD7310	Approved
0.7632	Intermediate Similarity	NPD7313	Approved
0.7632	Intermediate Similarity	NPD7311	Approved
0.7592	Intermediate Similarity	NPD7309	Approved
0.7568	Intermediate Similarity	NPD3051	Approved
0.7553	Intermediate Similarity	NPD6042	Phase 2
0.7553	Intermediate Similarity	NPD42	Phase 2
0.7542	Intermediate Similarity	NPD7261	Clinical (unspecified phase)
0.7539	Intermediate Similarity	NPD4577	Approved
0.7539	Intermediate Similarity	NPD4578	Approved
0.7534	Intermediate Similarity	NPD8152	Approved
0.7534	Intermediate Similarity	NPD8153	Approved
0.7527	Intermediate Similarity	NPD2969	Approved
0.7527	Intermediate Similarity	NPD2970	Approved
0.7514	Intermediate Similarity	NPD6107	Approved
0.7514	Intermediate Similarity	NPD7447	Phase 1
0.7513	Intermediate Similarity	NPD4663	Approved
0.7487	Intermediate Similarity	NPD2489	Approved
0.7487	Intermediate Similarity	NPD7549	Discontinued
0.7487	Intermediate Similarity	NPD27	Approved
0.7459	Intermediate Similarity	NPD7201	Clinical (unspecified phase)
0.7432	Intermediate Similarity	NPD2560	Approved
0.7432	Intermediate Similarity	NPD2563	Approved
0.7371	Intermediate Similarity	NPD7045	Clinical (unspecified phase)
0.736	Intermediate Similarity	NPD2421	Approved
0.736	Intermediate Similarity	NPD7213	Phase 3
0.736	Intermediate Similarity	NPD2420	Approved
0.736	Intermediate Similarity	NPD7212	Phase 2
0.7351	Intermediate Similarity	NPD4055	Discovery
0.7345	Intermediate Similarity	NPD5307	Clinical (unspecified phase)
0.732	Intermediate Similarity	NPD6853	Approved
0.732	Intermediate Similarity	NPD6851	Approved
0.7318	Intermediate Similarity	NPD1754	Clinical (unspecified phase)
0.7308	Intermediate Similarity	NPD4678	Approved
0.7308	Intermediate Similarity	NPD4675	Approved
0.7303	Intermediate Similarity	NPD2422	Clinical (unspecified phase)
0.7302	Intermediate Similarity	NPD2898	Approved
0.7299	Intermediate Similarity	NPD6028	Clinical (unspecified phase)
0.7299	Intermediate Similarity	NPD6029	Clinical (unspecified phase)
0.7292	Intermediate Similarity	NPD6297	Approved
0.7273	Intermediate Similarity	NPD5677	Discontinued
0.7268	Intermediate Similarity	NPD6072	Discontinued
0.7257	Intermediate Similarity	NPD1632	Clinical (unspecified phase)
0.724	Intermediate Similarity	NPD7479	Phase 2
0.7238	Intermediate Similarity	NPD5976	Discontinued
0.7232	Intermediate Similarity	NPD3060	Approved
0.7228	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.7225	Intermediate Similarity	NPD7827	Phase 1
0.7219	Intermediate Similarity	NPD5709	Phase 3
0.7211	Intermediate Similarity	NPD4481	Phase 3
0.7207	Intermediate Similarity	NPD7124	Phase 2
0.7196	Intermediate Similarity	NPD4010	Discontinued
0.7189	Intermediate Similarity	NPD4585	Approved
0.7182	Intermediate Similarity	NPD6090	Discontinued
0.7181	Intermediate Similarity	NPD4666	Phase 3
0.7158	Intermediate Similarity	NPD4017	Approved
0.7158	Intermediate Similarity	NPD6523	Clinical (unspecified phase)
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	NPD5241	Discontinued
0.7151	Intermediate Similarity	NPD2677	Approved
0.7143	Intermediate Similarity	NPD3640	Phase 3
0.7143	Intermediate Similarity	NPD3639	Approved
0.7143	Intermediate Similarity	NPD3641	Approved
0.7143	Intermediate Similarity	NPD2122	Discontinued
0.7143	Intermediate Similarity	NPD7802	Discontinued
0.7135	Intermediate Similarity	NPD4162	Approved
0.7129	Intermediate Similarity	NPD2975	Approved
0.7129	Intermediate Similarity	NPD2974	Approved
0.7129	Intermediate Similarity	NPD2973	Approved
0.7127	Intermediate Similarity	NPD4160	Clinical (unspecified phase)
0.711	Intermediate Similarity	NPD4475	Approved
0.711	Intermediate Similarity	NPD4474	Approved
0.7108	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7105	Intermediate Similarity	NPD4166	Phase 2
0.7098	Intermediate Similarity	NPD4873	Discontinued
0.7097	Intermediate Similarity	NPD2977	Approved
0.7097	Intermediate Similarity	NPD5773	Approved
0.7097	Intermediate Similarity	NPD5772	Approved
0.7097	Intermediate Similarity	NPD2978	Approved
0.7097	Intermediate Similarity	NPD7046	Clinical (unspecified phase)
0.7088	Intermediate Similarity	NPD5261	Clinical (unspecified phase)
0.7088	Intermediate Similarity	NPD3647	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD6997	Phase 2
0.7074	Intermediate Similarity	NPD7975	Clinical (unspecified phase)
0.7065	Intermediate Similarity	NPD4005	Discontinued
0.7059	Intermediate Similarity	NPD3837	Clinical (unspecified phase)
0.7056	Intermediate Similarity	NPD5160	Discontinued
0.7053	Intermediate Similarity	NPD4583	Approved
0.7053	Intermediate Similarity	NPD4582	Approved
0.705	Intermediate Similarity	NPD2488	Approved
0.705	Intermediate Similarity	NPD2490	Approved
0.7047	Intermediate Similarity	NPD5940	Clinical (unspecified phase)
0.7043	Intermediate Similarity	NPD3384	Approved
0.7043	Intermediate Similarity	NPD3383	Approved
0.7043	Intermediate Similarity	NPD3382	Approved
0.7043	Intermediate Similarity	NPD5722	Discontinued
0.7042	Intermediate Similarity	NPD7047	Phase 3
0.7039	Intermediate Similarity	NPD5177	Phase 3
0.7039	Intermediate Similarity	NPD5005	Approved
0.7039	Intermediate Similarity	NPD5006	Approved
0.7033	Intermediate Similarity	NPD4123	Phase 3
0.7024	Intermediate Similarity	NPD4580	Approved
0.7022	Intermediate Similarity	NPD2029	Clinical (unspecified phase)
0.7005	Intermediate Similarity	NPD4002	Approved
0.7005	Intermediate Similarity	NPD4004	Approved
0.7	Intermediate Similarity	NPD3977	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD6748	Discontinued
0.6995	Remote Similarity	NPD52	Approved
0.6995	Remote Similarity	NPD7526	Approved
0.6995	Remote Similarity	NPD7527	Clinical (unspecified phase)
0.6978	Remote Similarity	NPD1774	Approved
0.6978	Remote Similarity	NPD3124	Discontinued
0.6978	Remote Similarity	NPD6087	Phase 1
0.6971	Remote Similarity	NPD4040	Phase 1
0.697	Remote Similarity	NPD6618	Phase 2
0.697	Remote Similarity	NPD7090	Clinical (unspecified phase)
0.6961	Remote Similarity	NPD6284	Clinical (unspecified phase)
0.6959	Remote Similarity	NPD8155	Clinical (unspecified phase)
0.6959	Remote Similarity	NPD7493	Clinical (unspecified phase)
0.6954	Remote Similarity	NPD5718	Phase 2
0.6954	Remote Similarity	NPD4907	Clinical (unspecified phase)
0.6951	Remote Similarity	NPD6723	Discontinued
0.6949	Remote Similarity	NPD2200	Suspended
0.6939	Remote Similarity	NPD6996	Clinical (unspecified phase)
0.6936	Remote Similarity	NPD5752	Clinical (unspecified phase)
0.6934	Remote Similarity	NPD7783	Phase 2
0.6934	Remote Similarity	NPD7782	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD5312	Approved
0.6923	Remote Similarity	NPD6666	Approved
0.6923	Remote Similarity	NPD5313	Approved
0.6923	Remote Similarity	NPD6667	Approved
0.6919	Remote Similarity	NPD2971	Approved
0.6919	Remote Similarity	NPD2968	Approved
0.6919	Remote Similarity	NPD3686	Approved
0.6919	Remote Similarity	NPD3687	Approved
0.6915	Remote Similarity	NPD2845	Phase 2
0.6915	Remote Similarity	NPD2843	Phase 2
0.691	Remote Similarity	NPD2156	Approved
0.691	Remote Similarity	NPD2154	Approved
0.691	Remote Similarity	NPD2155	Approved
0.6906	Remote Similarity	NPD7466	Approved
0.6904	Remote Similarity	NPD7039	Approved
0.6904	Remote Similarity	NPD7038	Approved
0.6893	Remote Similarity	NPD2568	Approved
0.6889	Remote Similarity	NPD7153	Discontinued
0.6884	Remote Similarity	NPD8149	Discontinued
0.6882	Remote Similarity	NPD8158	Clinical (unspecified phase)
0.6878	Remote Similarity	NPD6621	Clinical (unspecified phase)
0.6869	Remote Similarity	NPD7132	Clinical (unspecified phase)
0.6868	Remote Similarity	NPD3692	Discontinued
0.6866	Remote Similarity	NPD8318	Clinical (unspecified phase)
0.6862	Remote Similarity	NPD7945	Clinical (unspecified phase)
0.6862	Remote Similarity	NPD5720	Discontinued
0.6854	Remote Similarity	NPD7718	Clinical (unspecified phase)
0.685	Remote Similarity	NPD5087	Clinical (unspecified phase)
0.6848	Remote Similarity	NPD7020	Approved
0.6848	Remote Similarity	NPD7019	Approved
0.6845	Remote Similarity	NPD4420	Approved
0.6842	Remote Similarity	NPD7773	Phase 2
0.6839	Remote Similarity	NPD1529	Clinical (unspecified phase)
0.6839	Remote Similarity	NPD4908	Phase 1
0.6831	Remote Similarity	NPD3122	Phase 3
0.6821	Remote Similarity	NPD5602	Clinical (unspecified phase)
0.6804	Remote Similarity	NPD8051	Clinical (unspecified phase)
0.68	Remote Similarity	NPD6494	Phase 2
0.68	Remote Similarity	NPD7922	Phase 1
0.68	Remote Similarity	NPD4625	Phase 3
0.6798	Remote Similarity	NPD5525	Clinical (unspecified phase)
0.6798	Remote Similarity	NPD3052	Approved

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