NPASS Compound

Structure

CID316989 OpenBabel06191716132D 42 45 0 0 1 0 0 0 0 0999 V2000 5.9438 -4.0841 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.0438 -1.6780 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.5341 0.8033 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5698 -2.8149 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.7650 -1.6197 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2034 3.6978 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8098 2.8687 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3736 2.0395 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9106 2.5765 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9945 -4.2091 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.1687 -0.7288 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4117 -3.4495 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.6821 1.2103 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7398 -1.7320 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5628 -0.7746 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.4091 -0.1459 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2034 -1.9303 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 4.8804 -1.2533 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 4.2034 0.3811 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5689 -1.2533 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2034 2.0395 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9106 -1.2533 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4624 -3.5745 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2459 0.3811 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5689 -0.2959 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2459 -1.9303 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 4.8804 -0.2959 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.2459 2.0395 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9106 -0.2959 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7672 1.2103 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7398 0.1829 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.5246 -0.5123 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0960 -4.4591 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.3996 -1.4616 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.6821 2.8687 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.7672 2.8687 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8523 1.2103 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7398 2.0977 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -1.5492 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 2.8796 -2.8149 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.7650 0.0705 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 10 1 0 0 0 0 2 11 1 0 0 0 0 3 16 1 0 0 0 0 6 35 1 0 0 0 0 7 36 1 0 0 0 0 8 37 1 0 0 0 0 9 38 1 0 0 0 0 10 12 1 0 0 0 0 11 16 2 0 0 0 0 12 23 1 0 0 0 0 13 19 2 0 0 0 0 13 21 1 0 0 0 0 14 20 2 0 0 0 0 14 22 1 0 0 0 0 15 39 1 0 0 0 0 15 40 1 0 0 0 0 16 32 1 0 0 0 0 17 4 1 1 0 0 0 17 18 1 0 0 0 0 17 26 1 0 0 0 0 18 5 1 1 0 0 0 18 27 1 0 0 0 0 19 24 1 0 0 0 0 19 27 1 0 0 0 0 20 25 1 0 0 0 0 20 26 1 0 0 0 0 21 28 2 0 0 0 0 21 35 1 0 0 0 0 22 29 2 0 0 0 0 22 39 1 0 0 0 0 23 33 2 0 0 0 0 23 41 1 0 0 0 0 24 25 1 0 0 0 0 24 30 2 0 0 0 0 25 31 2 0 0 0 0 26 41 1 1 0 0 0 27 42 1 6 0 0 0 28 30 1 0 0 0 0 28 36 1 0 0 0 0 29 31 1 0 0 0 0 29 40 1 0 0 0 0 30 37 1 0 0 0 0 31 38 1 0 0 0 0 32 34 2 0 0 0 0 32 42 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	584.26
Volume:	591.976
LogP:	4.626
LogD:	4.14
LogS:	-5.948
# Rotatable Bonds:	11
TPSA:	107.98
# H-Bond Aceptor:	10
# H-Bond Donor:	0
# Rings:	4
# Heavy Atoms:	10

MedChem Properties

QED Drug-Likeness Score:	0.245
Synthetic Accessibility Score:	4.399
Fsp3:	0.5
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
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:	-4.778
MDCK Permeability:	2.071255221380852e-05
Pgp-inhibitor:	1.0
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.0
30% Bioavailability (F30%):	0.049

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.035
Plasma Protein Binding (PPB):	78.50328826904297%
Volume Distribution (VD):	0.955
Pgp-substrate:	11.957853317260742%

ADMET: Metabolism

CYP1A2-inhibitor:	0.053
CYP1A2-substrate:	0.977
CYP2C19-inhibitor:	0.972
CYP2C19-substrate:	0.923
CYP2C9-inhibitor:	0.963
CYP2C9-substrate:	0.782
CYP2D6-inhibitor:	0.225
CYP2D6-substrate:	0.329
CYP3A4-inhibitor:	0.955
CYP3A4-substrate:	0.918

ADMET: Excretion

Clearance (CL):	3.965
Half-life (T1/2):	0.151

ADMET: Toxicity

hERG Blockers:	0.238
Human Hepatotoxicity (H-HT):	0.098
Drug-inuced Liver Injury (DILI):	0.874
AMES Toxicity:	0.028
Rat Oral Acute Toxicity:	0.05
Maximum Recommended Daily Dose:	0.036
Skin Sensitization:	0.051
Carcinogencity:	0.036
Eye Corrosion:	0.003
Eye Irritation:	0.059
Respiratory Toxicity:	0.125

Download Data

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

Natural Product: NPC316989

Natural Product ID:	NPC316989
*Common Name:**	Ananolignan N
IUPAC Name:	n.a.
Synonyms:	Ananolignan N
Standard InCHIKey:	YWOQCMUIZIFGSH-NWTVNDALSA-N
Standard InCHI:	InChI=1S/C32H40O10/c1-10-12-23(33)41-26-17(4)18(5)27(42-32(34)16(3)11-2)19-13-21(35-6)28(36-7)30(37-8)24(19)25-20(26)14-22-29(31(25)38-9)40-15-39-22/h11,13-14,17-18,26-27H,10,12,15H2,1-9H3/b16-11-/t17-,18+,26-,27-/m1/s1
SMILES:	CCCC(=O)O[C@@H]1[C@H](C)[C@H](C)[C@@H](OC(=O)/C(=CC)/C)c2c(c3c1cc1OCOc1c3OC)c(OC)c(c(c2)OC)OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1782122
PubChem CID:	53355574
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000238] Tannins [CHEMONTID:0001710] Hydrolyzable tannins

*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
NPO27599	Kadsura ananosma	Species	Schisandraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15165154]
NPO27599	Kadsura ananosma	Species	Schisandraceae	Eukaryota	Stems	n.a.	n.a.	PMID[20025236]
NPO27599	Kadsura ananosma	Species	Schisandraceae	Eukaryota	n.a.	seed	n.a.	PMID[21381710]
NPO27599	Kadsura ananosma	Species	Schisandraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO27599	Kadsura ananosma	Species	Schisandraceae	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
Others	2

Activity Type	# Activity
Cell Line	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT519	Cell Line	SH-SY5Y	Homo sapiens	Activity	=	75.0	%	PMID[559782]
NPT519	Cell Line	SH-SY5Y	Homo sapiens	Activity	=	66.8	%	PMID[559782]

☑ 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 NPC316989 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	1497
0.2-0.3	3535
0.3-0.4	8684
0.4-0.5	10092
0.5-0.6	3890
0.6-0.7	8516
0.7-0.8	5572
0.8-0.85	349
0.85-0.9	110
0.9-0.95	37
0.95-1	27

Similarity Score	Similarity Level	Natural Product ID
0.993	High Similarity	NPC477374
0.993	High Similarity	NPC477376
0.993	High Similarity	NPC322426
0.9859	High Similarity	NPC477375
0.9859	High Similarity	NPC252281
0.9859	High Similarity	NPC327352
0.9859	High Similarity	NPC198129
0.9718	High Similarity	NPC321958
0.9718	High Similarity	NPC321696
0.9658	High Similarity	NPC477377
0.9653	High Similarity	NPC85141
0.9648	High Similarity	NPC318286
0.9648	High Similarity	NPC327651
0.9589	High Similarity	NPC475229
0.9589	High Similarity	NPC477378
0.9577	High Similarity	NPC326144
0.953	High Similarity	NPC477885
0.9524	High Similarity	NPC126405
0.9524	High Similarity	NPC16791
0.9524	High Similarity	NPC77237
0.9524	High Similarity	NPC24562
0.9524	High Similarity	NPC297271
0.9524	High Similarity	NPC217708
0.9524	High Similarity	NPC308739
0.9524	High Similarity	NPC53669
0.9507	High Similarity	NPC76415
0.9507	High Similarity	NPC218510
0.9463	High Similarity	NPC477380
0.9459	High Similarity	NPC348849
0.9459	High Similarity	NPC178195
0.94	High Similarity	NPC475592
0.9396	High Similarity	NPC476065
0.9388	High Similarity	NPC224472
0.9342	High Similarity	NPC319749
0.9333	High Similarity	NPC473323
0.9329	High Similarity	NPC198461
0.9329	High Similarity	NPC312763
0.9262	High Similarity	NPC474606
0.9257	High Similarity	NPC303519
0.9211	High Similarity	NPC325122
0.92	High Similarity	NPC473425
0.9195	High Similarity	NPC471154
0.9184	High Similarity	NPC316676
0.9184	High Similarity	NPC325720
0.9161	High Similarity	NPC477884
0.9155	High Similarity	NPC865
0.9139	High Similarity	NPC238834
0.9128	High Similarity	NPC475756
0.9116	High Similarity	NPC295297
0.9091	High Similarity	NPC258322
0.9091	High Similarity	NPC191352
0.9085	High Similarity	NPC215400
0.9085	High Similarity	NPC230531
0.9079	High Similarity	NPC29727
0.906	High Similarity	NPC473989
0.9032	High Similarity	NPC280778
0.9007	High Similarity	NPC474514
0.9	High Similarity	NPC477379
0.8993	High Similarity	NPC474393
0.8993	High Similarity	NPC474347
0.8981	High Similarity	NPC118162
0.8981	High Similarity	NPC320471
0.8981	High Similarity	NPC83049
0.8951	High Similarity	NPC143895
0.8944	High Similarity	NPC185680
0.8944	High Similarity	NPC145722
0.8944	High Similarity	NPC256776
0.8933	High Similarity	NPC477381
0.8933	High Similarity	NPC470916
0.8931	High Similarity	NPC477883
0.8903	High Similarity	NPC63061
0.8889	High Similarity	NPC117154
0.8859	High Similarity	NPC137352
0.8859	High Similarity	NPC183083
0.8844	High Similarity	NPC324962
0.882	High Similarity	NPC477881
0.8819	High Similarity	NPC11453
0.8819	High Similarity	NPC32189
0.8816	High Similarity	NPC220577
0.8805	High Similarity	NPC311912
0.8805	High Similarity	NPC79322
0.88	High Similarity	NPC477879
0.879	High Similarity	NPC61141
0.8784	High Similarity	NPC474036
0.8784	High Similarity	NPC18211
0.8784	High Similarity	NPC143092
0.8784	High Similarity	NPC475000
0.8776	High Similarity	NPC230538
0.8776	High Similarity	NPC103637
0.8776	High Similarity	NPC36531
0.8776	High Similarity	NPC229172
0.8767	High Similarity	NPC103448
0.8767	High Similarity	NPC216434
0.8758	High Similarity	NPC475141
0.8758	High Similarity	NPC149735
0.875	High Similarity	NPC88557
0.875	High Similarity	NPC210642
0.875	High Similarity	NPC13985
0.8732	High Similarity	NPC184928
0.8732	High Similarity	NPC141493
0.8725	High Similarity	NPC475868
0.8718	High Similarity	NPC173726
0.8718	High Similarity	NPC241600
0.8701	High Similarity	NPC473736
0.8701	High Similarity	NPC273578
0.8699	High Similarity	NPC290714
0.8699	High Similarity	NPC201404
0.8699	High Similarity	NPC53722
0.8693	High Similarity	NPC104353
0.8684	High Similarity	NPC149505
0.8675	High Similarity	NPC262804
0.8675	High Similarity	NPC40654
0.8675	High Similarity	NPC304821
0.8667	High Similarity	NPC193779
0.8667	High Similarity	NPC474054
0.8659	High Similarity	NPC477882
0.8659	High Similarity	NPC477880
0.8658	High Similarity	NPC87883
0.8658	High Similarity	NPC172171
0.8658	High Similarity	NPC121661
0.8658	High Similarity	NPC239254
0.8658	High Similarity	NPC73467
0.8649	High Similarity	NPC474295
0.8649	High Similarity	NPC151423
0.8649	High Similarity	NPC287124
0.8649	High Similarity	NPC40237
0.8616	High Similarity	NPC475865
0.8616	High Similarity	NPC469475
0.8616	High Similarity	NPC469518
0.86	High Similarity	NPC474158
0.86	High Similarity	NPC197352
0.86	High Similarity	NPC166506
0.86	High Similarity	NPC189239
0.86	High Similarity	NPC110763
0.8571	High Similarity	NPC471180
0.8562	High Similarity	NPC24425
0.8553	High Similarity	NPC473445
0.8553	High Similarity	NPC469512
0.8544	High Similarity	NPC474770
0.8543	High Similarity	NPC252286
0.8543	High Similarity	NPC154971
0.8543	High Similarity	NPC87295
0.8542	High Similarity	NPC475856
0.8542	High Similarity	NPC65183
0.8542	High Similarity	NPC261812
0.8542	High Similarity	NPC72046
0.8535	High Similarity	NPC207584
0.8535	High Similarity	NPC19947
0.8533	High Similarity	NPC477701
0.8533	High Similarity	NPC166884
0.8533	High Similarity	NPC218841
0.8533	High Similarity	NPC141569
0.8533	High Similarity	NPC92693
0.8523	High Similarity	NPC184684
0.8523	High Similarity	NPC210354
0.8523	High Similarity	NPC184641
0.8523	High Similarity	NPC133934
0.8523	High Similarity	NPC176586
0.8521	High Similarity	NPC149008
0.8521	High Similarity	NPC207702
0.8521	High Similarity	NPC283114
0.8516	High Similarity	NPC245948
0.8503	High Similarity	NPC196420
0.85	High Similarity	NPC291977
0.8493	Intermediate Similarity	NPC44245
0.8493	Intermediate Similarity	NPC25333
0.8493	Intermediate Similarity	NPC148893
0.8493	Intermediate Similarity	NPC49235
0.8493	Intermediate Similarity	NPC72796
0.8487	Intermediate Similarity	NPC101755
0.8487	Intermediate Similarity	NPC80230
0.8487	Intermediate Similarity	NPC104024
0.8487	Intermediate Similarity	NPC304687
0.8487	Intermediate Similarity	NPC65574
0.8483	Intermediate Similarity	NPC1474
0.8483	Intermediate Similarity	NPC266848
0.8483	Intermediate Similarity	NPC136750
0.8481	Intermediate Similarity	NPC474043
0.8477	Intermediate Similarity	NPC477702
0.8476	Intermediate Similarity	NPC474568
0.8471	Intermediate Similarity	NPC32373
0.8471	Intermediate Similarity	NPC237946
0.8471	Intermediate Similarity	NPC301897
0.8467	Intermediate Similarity	NPC474288
0.8457	Intermediate Similarity	NPC42230
0.8456	Intermediate Similarity	NPC312199
0.8452	Intermediate Similarity	NPC302610
0.8447	Intermediate Similarity	NPC474647
0.8447	Intermediate Similarity	NPC475953
0.8438	Intermediate Similarity	NPC249070
0.8438	Intermediate Similarity	NPC42797
0.8435	Intermediate Similarity	NPC121651
0.8431	Intermediate Similarity	NPC102934
0.8431	Intermediate Similarity	NPC252402
0.8428	Intermediate Similarity	NPC96593
0.8425	Intermediate Similarity	NPC31530
0.8425	Intermediate Similarity	NPC145769
0.8421	Intermediate Similarity	NPC212890
0.8415	Intermediate Similarity	NPC471181
0.8415	Intermediate Similarity	NPC178737

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 NPC316989 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	320
0.1-0.2	927
0.2-0.3	1820
0.3-0.4	2747
0.4-0.5	1763
0.5-0.6	988
0.6-0.7	492
0.7-0.8	85
0.8-0.85	8
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8516	High Similarity	NPD37	Approved
0.8471	Intermediate Similarity	NPD4966	Approved
0.8471	Intermediate Similarity	NPD4967	Phase 2
0.8471	Intermediate Similarity	NPD4965	Approved
0.8365	Intermediate Similarity	NPD6234	Discontinued
0.8194	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.8148	Intermediate Similarity	NPD7199	Phase 2
0.8121	Intermediate Similarity	NPD7228	Approved
0.8049	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.8028	Intermediate Similarity	NPD3705	Approved
0.7929	Intermediate Similarity	NPD7240	Approved
0.7692	Intermediate Similarity	NPD3818	Discontinued
0.7688	Intermediate Similarity	NPD1653	Approved
0.7658	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7651	Intermediate Similarity	NPD5494	Approved
0.7647	Intermediate Similarity	NPD5844	Phase 1
0.7644	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7633	Intermediate Similarity	NPD7473	Discontinued
0.7576	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7561	Intermediate Similarity	NPD7819	Suspended
0.756	Intermediate Similarity	NPD6232	Discontinued
0.7515	Intermediate Similarity	NPD3817	Phase 2
0.75	Intermediate Similarity	NPD7266	Discontinued
0.75	Intermediate Similarity	NPD7074	Phase 3
0.7483	Intermediate Similarity	NPD3027	Phase 3
0.7455	Intermediate Similarity	NPD1465	Phase 2
0.7453	Intermediate Similarity	NPD1940	Clinical (unspecified phase)
0.7442	Intermediate Similarity	NPD7054	Approved
0.7414	Intermediate Similarity	NPD6559	Discontinued
0.7405	Intermediate Similarity	NPD6674	Discontinued
0.7399	Intermediate Similarity	NPD7472	Approved
0.7396	Intermediate Similarity	NPD8127	Discontinued
0.7386	Intermediate Similarity	NPD7090	Clinical (unspecified phase)
0.7381	Intermediate Similarity	NPD919	Approved
0.7372	Intermediate Similarity	NPD3748	Approved
0.7371	Intermediate Similarity	NPD7808	Phase 3
0.7351	Intermediate Similarity	NPD3018	Phase 2
0.7346	Intermediate Similarity	NPD7314	Clinical (unspecified phase)
0.7325	Intermediate Similarity	NPD2438	Suspended
0.732	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7318	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7314	Intermediate Similarity	NPD7685	Pre-registration
0.731	Intermediate Similarity	NPD3926	Phase 2
0.731	Intermediate Similarity	NPD5536	Phase 2
0.7305	Intermediate Similarity	NPD5353	Approved
0.7289	Intermediate Similarity	NPD1934	Approved
0.7283	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD5283	Phase 1
0.7273	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7262	Intermediate Similarity	NPD3882	Suspended
0.7251	Intermediate Similarity	NPD7229	Phase 3
0.7248	Intermediate Similarity	NPD2981	Phase 2
0.7246	Intermediate Similarity	NPD8455	Phase 2
0.7233	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7226	Intermediate Similarity	NPD1613	Approved
0.7226	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7219	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7219	Intermediate Similarity	NPD7975	Clinical (unspecified phase)
0.7219	Intermediate Similarity	NPD7680	Approved
0.7216	Intermediate Similarity	NPD7251	Discontinued
0.7211	Intermediate Similarity	NPD5691	Approved
0.7209	Intermediate Similarity	NPD5242	Approved
0.72	Intermediate Similarity	NPD2983	Phase 2
0.72	Intermediate Similarity	NPD2982	Phase 2
0.7179	Intermediate Similarity	NPD6355	Discontinued
0.7179	Intermediate Similarity	NPD1933	Approved
0.7178	Intermediate Similarity	NPD2533	Approved
0.7178	Intermediate Similarity	NPD2534	Approved
0.7178	Intermediate Similarity	NPD2532	Approved
0.7167	Intermediate Similarity	NPD6841	Approved
0.7167	Intermediate Similarity	NPD6843	Phase 3
0.7167	Intermediate Similarity	NPD6842	Approved
0.7166	Intermediate Similarity	NPD5006	Approved
0.7166	Intermediate Similarity	NPD5005	Approved
0.7159	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7159	Intermediate Similarity	NPD6797	Phase 2
0.7143	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD3750	Approved
0.7143	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7124	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7118	Intermediate Similarity	NPD7075	Discontinued
0.7117	Intermediate Similarity	NPD6799	Approved
0.7115	Intermediate Similarity	NPD2979	Phase 3
0.7115	Intermediate Similarity	NPD4060	Phase 1
0.7108	Intermediate Similarity	NPD6055	Clinical (unspecified phase)
0.7107	Intermediate Similarity	NPD2796	Approved
0.7093	Intermediate Similarity	NPD1247	Approved
0.7078	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7069	Intermediate Similarity	NPD6166	Phase 2
0.7069	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7069	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7066	Intermediate Similarity	NPD6599	Discontinued
0.7063	Intermediate Similarity	NPD5762	Approved
0.7063	Intermediate Similarity	NPD5763	Approved
0.7059	Intermediate Similarity	NPD7768	Phase 2
0.7049	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7045	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7043	Intermediate Similarity	NPD4420	Approved
0.7041	Intermediate Similarity	NPD2801	Approved
0.7039	Intermediate Similarity	NPD8312	Approved
0.7039	Intermediate Similarity	NPD8313	Approved
0.7037	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.7037	Intermediate Similarity	NPD4110	Phase 3
0.7024	Intermediate Similarity	NPD6386	Approved
0.7024	Intermediate Similarity	NPD6385	Approved
0.7012	Intermediate Similarity	NPD4357	Discontinued
0.7	Intermediate Similarity	NPD5402	Approved
0.6994	Remote Similarity	NPD5307	Clinical (unspecified phase)
0.6989	Remote Similarity	NPD3751	Discontinued
0.6988	Remote Similarity	NPD920	Approved
0.6983	Remote Similarity	NPD7549	Discontinued
0.6982	Remote Similarity	NPD6801	Discontinued
0.6981	Remote Similarity	NPD7097	Phase 1
0.6975	Remote Similarity	NPD1243	Approved
0.6974	Remote Similarity	NPD4379	Clinical (unspecified phase)
0.6968	Remote Similarity	NPD6832	Phase 2
0.6968	Remote Similarity	NPD4908	Phase 1
0.6964	Remote Similarity	NPD7028	Phase 2
0.6964	Remote Similarity	NPD4380	Phase 2
0.6962	Remote Similarity	NPD230	Phase 1
0.6954	Remote Similarity	NPD1281	Approved
0.6954	Remote Similarity	NPD3787	Discontinued
0.6943	Remote Similarity	NPD8151	Discontinued
0.6933	Remote Similarity	NPD4626	Approved
0.6933	Remote Similarity	NPD4628	Phase 3
0.6923	Remote Similarity	NPD8434	Phase 2
0.6923	Remote Similarity	NPD5089	Approved
0.6923	Remote Similarity	NPD5090	Approved
0.6905	Remote Similarity	NPD7458	Discontinued
0.6901	Remote Similarity	NPD6374	Clinical (unspecified phase)
0.6901	Remote Similarity	NPD8443	Clinical (unspecified phase)
0.6897	Remote Similarity	NPD6959	Discontinued
0.6894	Remote Similarity	NPD3539	Phase 1
0.6894	Remote Similarity	NPD2935	Discontinued
0.689	Remote Similarity	NPD5084	Clinical (unspecified phase)
0.689	Remote Similarity	NPD6190	Approved
0.6886	Remote Similarity	NPD5403	Approved
0.6879	Remote Similarity	NPD4907	Clinical (unspecified phase)
0.6871	Remote Similarity	NPD1652	Phase 2
0.6867	Remote Similarity	NPD5401	Approved
0.6867	Remote Similarity	NPD642	Clinical (unspecified phase)
0.6867	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6867	Remote Similarity	NPD5585	Approved
0.6867	Remote Similarity	NPD1357	Approved
0.6855	Remote Similarity	NPD5123	Clinical (unspecified phase)
0.6855	Remote Similarity	NPD5124	Phase 1
0.6853	Remote Similarity	NPD1358	Approved
0.6852	Remote Similarity	NPD3540	Phase 1
0.6848	Remote Similarity	NPD7235	Clinical (unspecified phase)
0.6848	Remote Similarity	NPD643	Clinical (unspecified phase)
0.6848	Remote Similarity	NPD7124	Phase 2
0.6842	Remote Similarity	NPD1610	Phase 2
0.6842	Remote Similarity	NPD1611	Approved
0.6842	Remote Similarity	NPD5563	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD4585	Approved
0.6842	Remote Similarity	NPD422	Phase 1
0.6839	Remote Similarity	NPD6917	Clinical (unspecified phase)
0.6835	Remote Similarity	NPD8032	Phase 2
0.6829	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.6824	Remote Similarity	NPD7615	Clinical (unspecified phase)
0.6824	Remote Similarity	NPD7411	Suspended
0.6821	Remote Similarity	NPD3749	Approved
0.6821	Remote Similarity	NPD17	Approved
0.6818	Remote Similarity	NPD1283	Approved
0.6815	Remote Similarity	NPD4625	Phase 3
0.6815	Remote Similarity	NPD7095	Approved
0.6807	Remote Similarity	NPD1511	Approved
0.6805	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6795	Remote Similarity	NPD2861	Phase 2
0.679	Remote Similarity	NPD2531	Phase 2
0.679	Remote Similarity	NPD6099	Approved
0.679	Remote Similarity	NPD6100	Approved
0.6783	Remote Similarity	NPD3134	Approved
0.678	Remote Similarity	NPD7852	Clinical (unspecified phase)
0.678	Remote Similarity	NPD4481	Phase 3
0.6774	Remote Similarity	NPD3266	Approved
0.6774	Remote Similarity	NPD7296	Approved
0.6774	Remote Similarity	NPD3267	Approved
0.6774	Remote Similarity	NPD2797	Approved
0.6772	Remote Similarity	NPD6798	Discontinued
0.6772	Remote Similarity	NPD1296	Phase 2
0.677	Remote Similarity	NPD6111	Discontinued
0.6755	Remote Similarity	NPD1651	Approved
0.6752	Remote Similarity	NPD1008	Clinical (unspecified phase)
0.675	Remote Similarity	NPD1899	Clinical (unspecified phase)
0.675	Remote Similarity	NPD447	Suspended
0.675	Remote Similarity	NPD3657	Discovery
0.6732	Remote Similarity	NPD1091	Approved
0.6728	Remote Similarity	NPD4108	Discontinued
0.6728	Remote Similarity	NPD1510	Phase 2
0.6727	Remote Similarity	NPD8166	Discontinued
0.6726	Remote Similarity	NPD1512	Approved
0.6726	Remote Similarity	NPD6273	Approved
0.6725	Remote Similarity	NPD6873	Phase 2
0.6724	Remote Similarity	NPD4055	Discovery
0.671	Remote Similarity	NPD1876	Approved
0.6708	Remote Similarity	NPD6653	Approved
0.6707	Remote Similarity	NPD7837	Clinical (unspecified phase)
0.6707	Remote Similarity	NPD5297	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