NPASS Compound

Structure

NPC308739 OpenBabel07101718222D 41 44 0 0 1 0 0 0 0 0999 V2000 3.1603 -0.4243 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6511 2.0547 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3103 -1.5601 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4683 -2.1941 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9483 0.1249 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6764 4.9464 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0677 4.1180 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5024 3.2896 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9660 3.8261 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2851 0.5240 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1376 -0.4783 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1981 2.4613 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.4379 0.4783 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5263 1.1063 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6764 -0.6764 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.4166 -2.3189 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3092 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6764 1.6329 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6764 3.2896 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9660 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3092 0.9565 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6329 1.6329 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6329 -0.6764 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.6329 3.2896 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9660 0.9565 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1111 2.4613 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1376 1.4348 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 0.9565 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.6426 0.7403 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.7827 -3.2026 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.5177 -0.2081 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.5823 -0.7589 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.1981 4.1180 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.1111 4.1180 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.0242 2.4613 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.1376 3.3478 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.8757 -0.2956 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.8757 1.2521 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.9989 -1.5601 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8837 1.3226 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 10 1 0 0 0 0 2 14 1 0 0 0 0 3 15 1 0 0 0 0 4 16 1 0 0 0 0 6 34 1 0 0 0 0 7 35 1 0 0 0 0 8 36 1 0 0 0 0 9 37 1 0 0 0 0 10 14 2 0 0 0 0 11 17 2 0 0 0 0 11 20 1 0 0 0 0 12 18 2 0 0 0 0 12 19 1 0 0 0 0 13 38 1 0 0 0 0 13 39 1 0 0 0 0 14 29 1 0 0 0 0 15 23 1 0 0 0 0 15 30 1 1 0 0 0 16 31 2 0 0 0 0 16 40 1 0 0 0 0 17 21 1 0 0 0 0 17 23 1 0 0 0 0 18 22 1 0 0 0 0 18 28 1 0 0 0 0 19 24 2 0 0 0 0 19 34 1 0 0 0 0 20 25 2 0 0 0 0 20 38 1 0 0 0 0 21 22 1 0 0 0 0 21 27 2 0 0 0 0 22 26 2 0 0 0 0 23 40 1 6 0 0 0 24 26 1 0 0 0 0 24 35 1 0 0 0 0 25 27 1 0 0 0 0 25 39 1 0 0 0 0 26 36 1 0 0 0 0 27 37 1 0 0 0 0 28 30 1 1 0 0 0 28 41 1 0 0 0 0 29 32 2 0 0 0 0 29 41 1 0 0 0 0 30 5 1 6 0 0 0 30 33 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	572.23
Volume:	566.175
LogP:	3.092
LogD:	2.785
LogS:	-4.135
# Rotatable Bonds:	9
TPSA:	128.21
# H-Bond Aceptor:	11
# H-Bond Donor:	1
# Rings:	4
# Heavy Atoms:	11

MedChem Properties

QED Drug-Likeness Score:	0.367
Synthetic Accessibility Score:	4.401
Fsp3:	0.467
Lipinski Rule-of-5:	Rejected
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:	-4.776
MDCK Permeability:	2.986047365993727e-05
Pgp-inhibitor:	0.997
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.009
20% Bioavailability (F20%):	0.001
30% Bioavailability (F30%):	0.054

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.106
Plasma Protein Binding (PPB):	72.58394622802734%
Volume Distribution (VD):	1.144
Pgp-substrate:	19.013290405273438%

ADMET: Metabolism

CYP1A2-inhibitor:	0.061
CYP1A2-substrate:	0.985
CYP2C19-inhibitor:	0.92
CYP2C19-substrate:	0.884
CYP2C9-inhibitor:	0.873
CYP2C9-substrate:	0.706
CYP2D6-inhibitor:	0.2
CYP2D6-substrate:	0.217
CYP3A4-inhibitor:	0.924
CYP3A4-substrate:	0.915

ADMET: Excretion

Clearance (CL):	4.754
Half-life (T1/2):	0.115

ADMET: Toxicity

hERG Blockers:	0.117
Human Hepatotoxicity (H-HT):	0.346
Drug-inuced Liver Injury (DILI):	0.842
AMES Toxicity:	0.055
Rat Oral Acute Toxicity:	0.195
Maximum Recommended Daily Dose:	0.06
Skin Sensitization:	0.105
Carcinogencity:	0.043
Eye Corrosion:	0.003
Eye Irritation:	0.118
Respiratory Toxicity:	0.491

Download Data

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

Natural Product: NPC308739

Natural Product ID:	NPC308739
*Common Name:**	Kadsurarin
IUPAC Name:	n.a.
Synonyms:	Kadsurarin
Standard InCHIKey:	DHEFJFKRWXSOLG-XKIHEKSBSA-N
Standard InCHI:	InChI=1S/C30H36O11/c1-10-14(2)29(32)41-28-18-12-19(34-6)24(35-7)26(36-8)22(18)21-17(11-20-25(27(21)37-9)39-13-38-20)23(40-16(4)31)15(3)30(28,5)33/h10-12,15,23,28,33H,13H2,1-9H3/b14-10-/t15-,23-,28+,30-/m0/s1
SMILES:	C/C=C(/C)C(=O)O[C@@H]1c2cc(c(c(c2-c2c(cc3c(c2OC)OCO3)[C@H]([C@H](C)[C@]1(C)O)OC(=O)C)OC)OC)OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL464501
PubChem CID:	44567619
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
NPO18146	Kadsura angustifolia	Species	Schisandraceae	Eukaryota	stems	Honghe Prefecture of Yunnan Province, China	2005-Oct	PMID[18278869]
NPO18146	Kadsura angustifolia	Species	Schisandraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21232955]
NPO18146	Kadsura angustifolia	Species	Schisandraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO18146	Kadsura angustifolia	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
EC50	1
Others	2

Activity Type	# Activity
Cell Line	1
Organism	1
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1452	Cell Line	C8166	Homo sapiens	CC50	>	200000.0	nM	PMID[560035]
NPT24	Organism	Human immunodeficiency virus 1	Human immunodeficiency virus 1	EC50	=	168310.0	nM	PMID[560035]
NPT2	Others	Unspecified		Ratio	>	2.14	n.a.	PMID[560035]

☑ 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 NPC308739 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	327
0.1-0.2	1376
0.2-0.3	3393
0.3-0.4	7948
0.4-0.5	10346
0.5-0.6	4350
0.6-0.7	7529
0.7-0.8	6711
0.8-0.85	557
0.85-0.9	91
0.9-0.95	47
0.95-1	22

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC77237
1.0	High Similarity	NPC217708
1.0	High Similarity	NPC16791
1.0	High Similarity	NPC126405
1.0	High Similarity	NPC53669
1.0	High Similarity	NPC297271
0.9862	High Similarity	NPC224472
0.9796	High Similarity	NPC198461
0.9732	High Similarity	NPC475592
0.973	High Similarity	NPC476065
0.9728	High Similarity	NPC24562
0.9655	High Similarity	NPC327352
0.9655	High Similarity	NPC252281
0.9655	High Similarity	NPC477375
0.9655	High Similarity	NPC198129
0.9589	High Similarity	NPC322426
0.9589	High Similarity	NPC477374
0.9589	High Similarity	NPC477376
0.9586	High Similarity	NPC295297
0.9533	High Similarity	NPC473323
0.953	High Similarity	NPC312763
0.9527	High Similarity	NPC471154
0.9524	High Similarity	NPC316989
0.9463	High Similarity	NPC474606
0.9459	High Similarity	NPC475756
0.9456	High Similarity	NPC85141
0.9448	High Similarity	NPC318286
0.9448	High Similarity	NPC327651
0.9408	High Similarity	NPC230531
0.9408	High Similarity	NPC215400
0.9404	High Similarity	NPC29727
0.9392	High Similarity	NPC470916
0.9388	High Similarity	NPC316676
0.9388	High Similarity	NPC325720
0.9384	High Similarity	NPC321958
0.9384	High Similarity	NPC321696
0.9379	High Similarity	NPC326144
0.9338	High Similarity	NPC238834
0.9333	High Similarity	NPC477377
0.9324	High Similarity	NPC474347
0.9324	High Similarity	NPC474393
0.931	High Similarity	NPC218510
0.931	High Similarity	NPC76415
0.9295	High Similarity	NPC118162
0.9295	High Similarity	NPC83049
0.9295	High Similarity	NPC320471
0.9272	High Similarity	NPC473425
0.9267	High Similarity	NPC475229
0.9267	High Similarity	NPC477378
0.9262	High Similarity	NPC473989
0.9189	High Similarity	NPC137352
0.9189	High Similarity	NPC183083
0.915	High Similarity	NPC477380
0.9145	High Similarity	NPC348849
0.9145	High Similarity	NPC178195
0.9133	High Similarity	NPC477381
0.9114	High Similarity	NPC79322
0.9097	High Similarity	NPC63061
0.9091	High Similarity	NPC477885
0.9079	High Similarity	NPC149735
0.9073	High Similarity	NPC477379
0.9057	High Similarity	NPC88557
0.9048	High Similarity	NPC324962
0.9034	High Similarity	NPC201404
0.9034	High Similarity	NPC290714
0.9034	High Similarity	NPC53722
0.902	High Similarity	NPC473736
0.9	High Similarity	NPC477883
0.8994	High Similarity	NPC311912
0.8993	High Similarity	NPC474054
0.8986	High Similarity	NPC87883
0.8986	High Similarity	NPC121661
0.8986	High Similarity	NPC73467
0.898	High Similarity	NPC36531
0.898	High Similarity	NPC103637
0.898	High Similarity	NPC230538
0.898	High Similarity	NPC229172
0.8966	High Similarity	NPC865
0.8954	High Similarity	NPC475141
0.8947	High Similarity	NPC303519
0.8926	High Similarity	NPC166506
0.8926	High Similarity	NPC110763
0.8926	High Similarity	NPC475868
0.8926	High Similarity	NPC197352
0.8926	High Similarity	NPC189239
0.8917	High Similarity	NPC319749
0.891	High Similarity	NPC325122
0.8889	High Similarity	NPC477881
0.8882	High Similarity	NPC24425
0.8874	High Similarity	NPC477879
0.8867	High Similarity	NPC154971
0.8867	High Similarity	NPC252286
0.8861	High Similarity	NPC280778
0.8861	High Similarity	NPC469512
0.8859	High Similarity	NPC172171
0.8859	High Similarity	NPC239254
0.8851	High Similarity	NPC184641
0.8851	High Similarity	NPC287124
0.8851	High Similarity	NPC133934
0.8851	High Similarity	NPC184684
0.8805	High Similarity	NPC469475
0.8805	High Similarity	NPC469518
0.88	High Similarity	NPC477702
0.8797	High Similarity	NPC191352
0.8797	High Similarity	NPC258322
0.879	High Similarity	NPC173726
0.879	High Similarity	NPC241600
0.8767	High Similarity	NPC143895
0.8766	High Similarity	NPC302610
0.8759	High Similarity	NPC145722
0.8759	High Similarity	NPC185680
0.8759	High Similarity	NPC256776
0.875	High Similarity	NPC477884
0.875	High Similarity	NPC304821
0.8742	High Similarity	NPC212890
0.8742	High Similarity	NPC42797
0.8733	High Similarity	NPC166884
0.8733	High Similarity	NPC141569
0.8733	High Similarity	NPC477701
0.8727	High Similarity	NPC477882
0.8727	High Similarity	NPC477880
0.8718	High Similarity	NPC117154
0.871	High Similarity	NPC474514
0.8688	High Similarity	NPC475865
0.8688	High Similarity	NPC291977
0.8649	High Similarity	NPC471183
0.8642	High Similarity	NPC471180
0.8639	High Similarity	NPC32189
0.8639	High Similarity	NPC11453
0.8627	High Similarity	NPC252402
0.8627	High Similarity	NPC93924
0.8627	High Similarity	NPC102934
0.8625	High Similarity	NPC473445
0.8621	High Similarity	NPC102256
0.8616	High Similarity	NPC474770
0.8608	High Similarity	NPC207584
0.8608	High Similarity	NPC19947
0.8598	High Similarity	NPC178737
0.8598	High Similarity	NPC471181
0.8591	High Similarity	NPC103448
0.8591	High Similarity	NPC216434
0.859	High Similarity	NPC245948
0.8581	High Similarity	NPC477700
0.8581	High Similarity	NPC32079
0.8571	High Similarity	NPC236522
0.8562	High Similarity	NPC152424
0.8562	High Similarity	NPC100465
0.8553	High Similarity	NPC328122
0.8552	High Similarity	NPC184928
0.8552	High Similarity	NPC141493
0.8544	High Similarity	NPC32373
0.8544	High Similarity	NPC237946
0.8526	High Similarity	NPC220577
0.8526	High Similarity	NPC470264
0.8519	High Similarity	NPC222531
0.8514	High Similarity	NPC133025
0.8509	High Similarity	NPC61141
0.8509	High Similarity	NPC249070
0.8506	High Similarity	NPC270751
0.85	High Similarity	NPC150943
0.85	High Similarity	NPC268718
0.85	High Similarity	NPC91634
0.85	High Similarity	NPC96593
0.8491	Intermediate Similarity	NPC115281
0.8491	Intermediate Similarity	NPC181168
0.8491	Intermediate Similarity	NPC163527
0.8487	Intermediate Similarity	NPC187774
0.8487	Intermediate Similarity	NPC472712
0.8487	Intermediate Similarity	NPC18211
0.8487	Intermediate Similarity	NPC143092
0.8487	Intermediate Similarity	NPC297342
0.8487	Intermediate Similarity	NPC472713
0.8487	Intermediate Similarity	NPC475000
0.8487	Intermediate Similarity	NPC473046
0.8487	Intermediate Similarity	NPC474036
0.8487	Intermediate Similarity	NPC118385
0.8485	Intermediate Similarity	NPC469506
0.8477	Intermediate Similarity	NPC41782
0.8477	Intermediate Similarity	NPC474295
0.8467	Intermediate Similarity	NPC46591
0.8467	Intermediate Similarity	NPC177868
0.8462	Intermediate Similarity	NPC13985
0.8462	Intermediate Similarity	NPC210642
0.8456	Intermediate Similarity	NPC301765
0.8456	Intermediate Similarity	NPC46277
0.8456	Intermediate Similarity	NPC474039
0.8456	Intermediate Similarity	NPC156948
0.8456	Intermediate Similarity	NPC283949
0.8456	Intermediate Similarity	NPC3072
0.8456	Intermediate Similarity	NPC86605
0.8452	Intermediate Similarity	NPC293757
0.8452	Intermediate Similarity	NPC477695
0.8452	Intermediate Similarity	NPC90896
0.8452	Intermediate Similarity	NPC668
0.8452	Intermediate Similarity	NPC474965
0.8452	Intermediate Similarity	NPC283839
0.8452	Intermediate Similarity	NPC174512
0.8452	Intermediate Similarity	NPC106138
0.8452	Intermediate Similarity	NPC477698
0.8447	Intermediate Similarity	NPC288149

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 NPC308739 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	285
0.1-0.2	881
0.2-0.3	1818
0.3-0.4	2739
0.4-0.5	1804
0.5-0.6	963
0.6-0.7	549
0.7-0.8	104
0.8-0.85	7
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.859	High Similarity	NPD37	Approved
0.8553	High Similarity	NPD6234	Discontinued
0.8544	High Similarity	NPD4967	Phase 2
0.8544	High Similarity	NPD4966	Approved
0.8544	High Similarity	NPD4965	Approved
0.8333	Intermediate Similarity	NPD7199	Phase 2
0.8303	Intermediate Similarity	NPD7228	Approved
0.8232	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.8107	Intermediate Similarity	NPD7240	Approved
0.7987	Intermediate Similarity	NPD1653	Approved
0.7925	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.787	Intermediate Similarity	NPD3818	Discontinued
0.7862	Intermediate Similarity	NPD3705	Approved
0.7816	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7806	Intermediate Similarity	NPD7266	Discontinued
0.78	Intermediate Similarity	NPD3027	Phase 3
0.7758	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7736	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7719	Intermediate Similarity	NPD5844	Phase 1
0.7707	Intermediate Similarity	NPD6674	Discontinued
0.7706	Intermediate Similarity	NPD7473	Discontinued
0.7674	Intermediate Similarity	NPD7074	Phase 3
0.7636	Intermediate Similarity	NPD1465	Phase 2
0.7633	Intermediate Similarity	NPD6232	Discontinued
0.7616	Intermediate Similarity	NPD7054	Approved
0.759	Intermediate Similarity	NPD3817	Phase 2
0.7586	Intermediate Similarity	NPD6559	Discontinued
0.7572	Intermediate Similarity	NPD7472	Approved
0.7557	Intermediate Similarity	NPD7090	Clinical (unspecified phase)
0.7532	Intermediate Similarity	NPD1613	Approved
0.7532	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.753	Intermediate Similarity	NPD7819	Suspended
0.7486	Intermediate Similarity	NPD7685	Pre-registration
0.747	Intermediate Similarity	NPD1934	Approved
0.7446	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.7443	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7443	Intermediate Similarity	NPD7808	Phase 3
0.744	Intermediate Similarity	NPD3882	Suspended
0.7434	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.743	Intermediate Similarity	NPD6843	Phase 3
0.743	Intermediate Similarity	NPD6842	Approved
0.743	Intermediate Similarity	NPD6841	Approved
0.7419	Intermediate Similarity	NPD4060	Phase 1
0.7412	Intermediate Similarity	NPD5494	Approved
0.7403	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7396	Intermediate Similarity	NPD7975	Clinical (unspecified phase)
0.7396	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7389	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7386	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7386	Intermediate Similarity	NPD7251	Discontinued
0.7372	Intermediate Similarity	NPD6355	Discontinued
0.7368	Intermediate Similarity	NPD8127	Discontinued
0.7358	Intermediate Similarity	NPD5763	Approved
0.7358	Intermediate Similarity	NPD5762	Approved
0.733	Intermediate Similarity	NPD6797	Phase 2
0.7329	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7326	Intermediate Similarity	NPD7229	Phase 3
0.7321	Intermediate Similarity	NPD8455	Phase 2
0.7321	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7321	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.732	Intermediate Similarity	NPD3018	Phase 2
0.7317	Intermediate Similarity	NPD7314	Clinical (unspecified phase)
0.7317	Intermediate Similarity	NPD1940	Clinical (unspecified phase)
0.7312	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7294	Intermediate Similarity	NPD7075	Discontinued
0.7287	Intermediate Similarity	NPD7680	Approved
0.7257	Intermediate Similarity	NPD3751	Discontinued
0.7256	Intermediate Similarity	NPD2533	Approved
0.7256	Intermediate Similarity	NPD2532	Approved
0.7256	Intermediate Similarity	NPD2534	Approved
0.7247	Intermediate Similarity	NPD7549	Discontinued
0.7241	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7241	Intermediate Similarity	NPD6166	Phase 2
0.7241	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7232	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7225	Intermediate Similarity	NPD3787	Discontinued
0.7222	Intermediate Similarity	NPD3750	Approved
0.7219	Intermediate Similarity	NPD2801	Approved
0.7213	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7195	Intermediate Similarity	NPD6799	Approved
0.7178	Intermediate Similarity	NPD6190	Approved
0.7171	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7171	Intermediate Similarity	NPD2982	Phase 2
0.7171	Intermediate Similarity	NPD2983	Phase 2
0.717	Intermediate Similarity	NPD7097	Phase 1
0.7161	Intermediate Similarity	NPD4908	Phase 1
0.716	Intermediate Similarity	NPD1652	Phase 2
0.7152	Intermediate Similarity	NPD5124	Phase 1
0.7152	Intermediate Similarity	NPD230	Phase 1
0.7152	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7151	Intermediate Similarity	NPD919	Approved
0.7143	Intermediate Similarity	NPD4380	Phase 2
0.7143	Intermediate Similarity	NPD7028	Phase 2
0.7143	Intermediate Similarity	NPD6599	Discontinued
0.7125	Intermediate Similarity	NPD3748	Approved
0.7123	Intermediate Similarity	NPD5283	Phase 1
0.7119	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7117	Intermediate Similarity	NPD4110	Phase 3
0.7117	Intermediate Similarity	NPD4628	Phase 3
0.7117	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.7115	Intermediate Similarity	NPD4625	Phase 3
0.7115	Intermediate Similarity	NPD7095	Approved
0.7111	Intermediate Similarity	NPD8313	Approved
0.7111	Intermediate Similarity	NPD8312	Approved
0.7105	Intermediate Similarity	NPD2981	Phase 2
0.7091	Intermediate Similarity	NPD4357	Discontinued
0.7088	Intermediate Similarity	NPD8434	Phase 2
0.7086	Intermediate Similarity	NPD3926	Phase 2
0.7081	Intermediate Similarity	NPD2438	Suspended
0.7076	Intermediate Similarity	NPD5353	Approved
0.7076	Intermediate Similarity	NPD5402	Approved
0.707	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7067	Intermediate Similarity	NPD5691	Approved
0.7067	Intermediate Similarity	NPD1357	Approved
0.7059	Intermediate Similarity	NPD6801	Discontinued
0.7047	Intermediate Similarity	NPD5536	Phase 2
0.7039	Intermediate Similarity	NPD1091	Approved
0.7039	Intermediate Similarity	NPD422	Phase 1
0.7039	Intermediate Similarity	NPD1610	Phase 2
0.7035	Intermediate Similarity	NPD7768	Phase 2
0.7032	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7027	Intermediate Similarity	NPD7296	Approved
0.702	Intermediate Similarity	NPD4626	Approved
0.7018	Intermediate Similarity	NPD5563	Clinical (unspecified phase)
0.701	Intermediate Similarity	NPD8151	Discontinued
0.7	Intermediate Similarity	NPD5090	Approved
0.7	Intermediate Similarity	NPD5089	Approved
0.6994	Remote Similarity	NPD3749	Approved
0.6989	Remote Similarity	NPD5242	Approved
0.6988	Remote Similarity	NPD1511	Approved
0.6987	Remote Similarity	NPD2861	Phase 2
0.6982	Remote Similarity	NPD7458	Discontinued
0.6982	Remote Similarity	NPD6055	Clinical (unspecified phase)
0.6981	Remote Similarity	NPD3619	Clinical (unspecified phase)
0.6981	Remote Similarity	NPD3620	Phase 2
0.6977	Remote Similarity	NPD6374	Clinical (unspecified phase)
0.6975	Remote Similarity	NPD2935	Discontinued
0.6975	Remote Similarity	NPD6099	Approved
0.6975	Remote Similarity	NPD6100	Approved
0.6971	Remote Similarity	NPD6959	Discontinued
0.6964	Remote Similarity	NPD5403	Approved
0.6963	Remote Similarity	NPD5006	Approved
0.6963	Remote Similarity	NPD5005	Approved
0.6962	Remote Similarity	NPD6410	Clinical (unspecified phase)
0.6962	Remote Similarity	NPD6798	Discontinued
0.6951	Remote Similarity	NPD5698	Clinical (unspecified phase)
0.6948	Remote Similarity	NPD4749	Approved
0.6946	Remote Similarity	NPD5401	Approved
0.6946	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6937	Remote Similarity	NPD1933	Approved
0.6928	Remote Similarity	NPD5058	Phase 3
0.6909	Remote Similarity	NPD7982	Clinical (unspecified phase)
0.6909	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.6905	Remote Similarity	NPD1512	Approved
0.6903	Remote Similarity	NPD1283	Approved
0.6901	Remote Similarity	NPD7411	Suspended
0.6901	Remote Similarity	NPD7615	Clinical (unspecified phase)
0.6894	Remote Similarity	NPD6653	Approved
0.689	Remote Similarity	NPD2424	Discontinued
0.6882	Remote Similarity	NPD4005	Discontinued
0.6882	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6879	Remote Similarity	NPD8443	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD4140	Approved
0.6875	Remote Similarity	NPD2979	Phase 3
0.6875	Remote Similarity	NPD1247	Approved
0.6871	Remote Similarity	NPD2796	Approved
0.6867	Remote Similarity	NPD5307	Clinical (unspecified phase)
0.6859	Remote Similarity	NPD2797	Approved
0.6855	Remote Similarity	NPD3764	Approved
0.6842	Remote Similarity	NPD4420	Approved
0.6839	Remote Similarity	NPD7435	Discontinued
0.6832	Remote Similarity	NPD447	Suspended
0.6829	Remote Similarity	NPD3540	Phase 1
0.6829	Remote Similarity	NPD1375	Discontinued
0.6813	Remote Similarity	NPD6233	Phase 2
0.681	Remote Similarity	NPD7033	Discontinued
0.681	Remote Similarity	NPD1510	Phase 2
0.681	Remote Similarity	NPD4108	Discontinued
0.6807	Remote Similarity	NPD3892	Phase 2
0.6807	Remote Similarity	NPD8166	Discontinued
0.6805	Remote Similarity	NPD6273	Approved
0.6802	Remote Similarity	NPD6386	Approved
0.6802	Remote Similarity	NPD6385	Approved
0.68	Remote Similarity	NPD4055	Discovery
0.6797	Remote Similarity	NPD5125	Phase 3
0.6797	Remote Similarity	NPD5126	Approved
0.6788	Remote Similarity	NPD1549	Phase 2
0.6776	Remote Similarity	NPD1548	Phase 1
0.6774	Remote Similarity	NPD1608	Approved
0.677	Remote Similarity	NPD1240	Approved
0.6768	Remote Similarity	NPD1551	Phase 2
0.6768	Remote Similarity	NPD6032	Approved
0.6768	Remote Similarity	NPD3539	Phase 1
0.6766	Remote Similarity	NPD5084	Clinical (unspecified phase)
0.6765	Remote Similarity	NPD920	Approved
0.676	Remote Similarity	NPD7852	Clinical (unspecified phase)
0.6753	Remote Similarity	NPD3496	Discontinued
0.675	Remote Similarity	NPD7985	Registered
0.675	Remote Similarity	NPD1699	Clinical (unspecified phase)
0.675	Remote Similarity	NPD7930	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