NPASS Compound

Structure

NPC475229 OpenBabel07101718242D 40 44 0 0 1 0 0 0 0 0999 V2000 5.7594 1.6181 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5654 2.8122 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1993 -3.6943 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8080 -2.8659 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3732 -2.0375 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9097 -2.5740 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.8347 3.8305 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.2524 3.0716 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.4687 4.7142 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.3041 3.1965 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.5203 4.8391 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9897 4.2050 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4074 3.4462 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8757 0.2956 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.6776 -1.2092 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7381 1.7304 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5622 0.7738 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8757 1.2521 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 4.1993 1.9285 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 5.9380 4.0802 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1993 -0.3808 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5665 1.2521 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1993 -2.0375 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9097 1.2521 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4591 3.5710 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2428 -0.3808 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5665 0.2956 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2428 1.9285 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.2428 -2.0375 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9097 0.2956 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7646 -1.2092 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7381 -0.1827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0930 4.4547 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.6776 -2.8659 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.7646 -2.8659 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8515 -1.2092 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7381 -2.0957 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 1.5477 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 2.8768 2.8122 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3 34 1 0 0 0 0 4 35 1 0 0 0 0 5 36 1 0 0 0 0 6 37 1 0 0 0 0 7 8 2 0 0 0 0 7 9 1 0 0 0 0 8 10 1 0 0 0 0 9 11 2 0 0 0 0 10 20 2 0 0 0 0 11 20 1 0 0 0 0 12 13 2 0 0 0 0 12 20 1 0 0 0 0 13 25 1 0 0 0 0 14 18 1 0 0 0 0 14 21 1 0 0 0 0 15 21 2 0 0 0 0 15 23 1 0 0 0 0 16 22 2 0 0 0 0 16 24 1 0 0 0 0 17 38 1 0 0 0 0 17 39 1 0 0 0 0 18 1 1 6 0 0 0 18 19 1 0 0 0 0 19 2 1 6 0 0 0 19 28 1 0 0 0 0 21 26 1 0 0 0 0 22 27 1 0 0 0 0 22 28 1 0 0 0 0 23 29 2 0 0 0 0 23 34 1 0 0 0 0 24 30 2 0 0 0 0 24 38 1 0 0 0 0 25 33 2 0 0 0 0 25 40 1 0 0 0 0 26 27 1 0 0 0 0 26 31 2 0 0 0 0 27 32 2 0 0 0 0 28 40 1 6 0 0 0 29 31 1 0 0 0 0 29 35 1 0 0 0 0 30 32 1 0 0 0 0 30 39 1 0 0 0 0 31 36 1 0 0 0 0 32 37 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	546.23
Volume:	560.566
LogP:	5.55
LogD:	4.62
LogS:	-6.824
# Rotatable Bonds:	8
TPSA:	81.68
# H-Bond Aceptor:	8
# H-Bond Donor:	0
# Rings:	5
# Heavy Atoms:	8

MedChem Properties

QED Drug-Likeness Score:	0.254
Synthetic Accessibility Score:	3.916
Fsp3:	0.344
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:	-4.799
MDCK Permeability:	1.7876642232295126e-05
Pgp-inhibitor:	1.0
Pgp-substrate:	0.007
Human Intestinal Absorption (HIA):	0.002
20% Bioavailability (F20%):	0.0
30% Bioavailability (F30%):	0.02

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.026
Plasma Protein Binding (PPB):	89.42804718017578%
Volume Distribution (VD):	0.485
Pgp-substrate:	7.1719465255737305%

ADMET: Metabolism

CYP1A2-inhibitor:	0.084
CYP1A2-substrate:	0.965
CYP2C19-inhibitor:	0.98
CYP2C19-substrate:	0.858
CYP2C9-inhibitor:	0.964
CYP2C9-substrate:	0.93
CYP2D6-inhibitor:	0.19
CYP2D6-substrate:	0.827
CYP3A4-inhibitor:	0.912
CYP3A4-substrate:	0.917

ADMET: Excretion

Clearance (CL):	5.009
Half-life (T1/2):	0.076

ADMET: Toxicity

hERG Blockers:	0.187
Human Hepatotoxicity (H-HT):	0.071
Drug-inuced Liver Injury (DILI):	0.925
AMES Toxicity:	0.095
Rat Oral Acute Toxicity:	0.012
Maximum Recommended Daily Dose:	0.152
Skin Sensitization:	0.533
Carcinogencity:	0.072
Eye Corrosion:	0.003
Eye Irritation:	0.282
Respiratory Toxicity:	0.079

Download Data

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

Natural Product: NPC475229

Natural Product ID:	NPC475229
*Common Name:**	Kadsuphilins A
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	QWIXWIQRZHRKNQ-OFJKUSFOSA-N
Standard InCHI:	InChI=1S/C32H34O8/c1-18-14-21-15-23(34-3)29(35-4)31(36-5)26(21)27-22(16-24-30(32(27)37-6)39-17-38-24)28(19(18)2)40-25(33)13-12-20-10-8-7-9-11-20/h7-13,15-16,18-19,28H,14,17H2,1-6H3/b13-12+/t18-,19-,28-/m1/s1
SMILES:	CC1CC2=CC(=C(C(=C2C3=C(C4=C(C=C3C(C1C)OC(=O)C=CC5=CC=CC=C5)OCO4)OC)OC)OC)OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL501443
PubChem CID:	12004412
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
NPO22075	Kadsura philippinensis	Species	Schisandraceae	Eukaryota	n.a.	stem	n.a.	PMID[16018647]
NPO22075	Kadsura philippinensis	Species	Schisandraceae	Eukaryota	n.a.	leaf	n.a.	PMID[16018647]
NPO22075	Kadsura philippinensis	Species	Schisandraceae	Eukaryota	n.a.	aerial part	n.a.	PMID[16268562]
NPO22075	Kadsura philippinensis	Species	Schisandraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16792420]
NPO22075	Kadsura philippinensis	Species	Schisandraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17608535]
NPO23565	Kadsura polysperma	Species	Schisandraceae	Eukaryota	stems	Emei County of Sichuan Province, China	2009-AUG	PMID[22329624]
NPO23565	Kadsura polysperma	Species	Schisandraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22075	Kadsura philippinensis	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
ED50	3
Others	5

Activity Type	# Activity
Cell Line	6
NON-MOLECULAR	1
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT91	Cell Line	KB	Homo sapiens	ED50	>=	5.0	ug ml-1	PMID[504597]
NPT165	Cell Line	HeLa	Homo sapiens	ED50	>=	5.0	ug ml-1	PMID[504597]
NPT681	Cell Line	PC-12	Rattus norvegicus	Activity	=	35.3	%	PMID[504598]
NPT681	Cell Line	PC-12	Rattus norvegicus	Activity	=	32.3	%	PMID[504598]
NPT681	Cell Line	PC-12	Rattus norvegicus	Activity	=	53.0	%	PMID[504598]
NPT681	Cell Line	PC-12	Rattus norvegicus	Activity	=	52.5	%	PMID[504598]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	ED50	>=	5.0	ug ml-1	PMID[504597]
NPT1	Others	Radical scavenging activity		Activity	=	1.5	%	PMID[504597]

☑ 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 NPC475229 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	415
0.1-0.2	1595
0.2-0.3	3836
0.3-0.4	9789
0.4-0.5	8874
0.5-0.6	3925
0.6-0.7	8202
0.7-0.8	5484
0.8-0.85	421
0.85-0.9	100
0.9-0.95	44
0.95-1	12

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC477378
0.9931	High Similarity	NPC477377
0.9655	High Similarity	NPC477376
0.9655	High Similarity	NPC322426
0.9655	High Similarity	NPC477374
0.9589	High Similarity	NPC316989
0.9586	High Similarity	NPC252281
0.9586	High Similarity	NPC327352
0.9586	High Similarity	NPC198129
0.9586	High Similarity	NPC477375
0.9474	High Similarity	NPC319749
0.947	High Similarity	NPC215400
0.947	High Similarity	NPC230531
0.9444	High Similarity	NPC326144
0.9388	High Similarity	NPC85141
0.9379	High Similarity	NPC327651
0.9379	High Similarity	NPC318286
0.9375	High Similarity	NPC218510
0.9375	High Similarity	NPC76415
0.9315	High Similarity	NPC321958
0.9315	High Similarity	NPC321696
0.929	High Similarity	NPC477884
0.9267	High Similarity	NPC77237
0.9267	High Similarity	NPC24562
0.9267	High Similarity	NPC16791
0.9267	High Similarity	NPC308739
0.9267	High Similarity	NPC217708
0.9267	High Similarity	NPC297271
0.9267	High Similarity	NPC126405
0.9267	High Similarity	NPC53669
0.9262	High Similarity	NPC224472
0.9221	High Similarity	NPC258322
0.9221	High Similarity	NPC191352
0.9161	High Similarity	NPC280778
0.915	High Similarity	NPC477885
0.915	High Similarity	NPC475592
0.9145	High Similarity	NPC476065
0.9139	High Similarity	NPC475141
0.9108	High Similarity	NPC320471
0.9108	High Similarity	NPC83049
0.9108	High Similarity	NPC118162
0.9085	High Similarity	NPC477380
0.9085	High Similarity	NPC473323
0.9079	High Similarity	NPC178195
0.9079	High Similarity	NPC312763
0.9079	High Similarity	NPC348849
0.9079	High Similarity	NPC198461
0.9079	High Similarity	NPC473736
0.906	High Similarity	NPC325720
0.906	High Similarity	NPC316676
0.9057	High Similarity	NPC477883
0.9028	High Similarity	NPC865
0.8958	High Similarity	NPC143895
0.8947	High Similarity	NPC471154
0.8944	High Similarity	NPC477881
0.894	High Similarity	NPC473989
0.8931	High Similarity	NPC311912
0.8931	High Similarity	NPC79322
0.8889	High Similarity	NPC474606
0.8882	High Similarity	NPC475756
0.8882	High Similarity	NPC303519
0.8875	High Similarity	NPC88557
0.8867	High Similarity	NPC295297
0.8846	High Similarity	NPC325122
0.8831	High Similarity	NPC473425
0.8819	High Similarity	NPC256776
0.8819	High Similarity	NPC145722
0.8819	High Similarity	NPC185680
0.8808	High Similarity	NPC252402
0.8808	High Similarity	NPC102934
0.878	High Similarity	NPC477882
0.878	High Similarity	NPC477880
0.8774	High Similarity	NPC238834
0.8767	High Similarity	NPC196420
0.8758	High Similarity	NPC477379
0.875	High Similarity	NPC474393
0.875	High Similarity	NPC474347
0.8725	High Similarity	NPC324962
0.8718	High Similarity	NPC29727
0.8699	High Similarity	NPC11453
0.8699	High Similarity	NPC32189
0.8693	High Similarity	NPC470916
0.8693	High Similarity	NPC477381
0.8693	High Similarity	NPC24425
0.8679	High Similarity	NPC473445
0.8658	High Similarity	NPC230538
0.8658	High Similarity	NPC103637
0.8658	High Similarity	NPC229172
0.8658	High Similarity	NPC36531
0.8654	High Similarity	NPC117154
0.8649	High Similarity	NPC103448
0.8649	High Similarity	NPC216434
0.8645	High Similarity	NPC474514
0.8636	High Similarity	NPC13985
0.8636	High Similarity	NPC210642
0.8625	High Similarity	NPC291977
0.8618	High Similarity	NPC137352
0.8618	High Similarity	NPC183083
0.8611	High Similarity	NPC184928
0.8611	High Similarity	NPC141493
0.8609	High Similarity	NPC475868
0.8608	High Similarity	NPC173726
0.8608	High Similarity	NPC241600
0.859	High Similarity	NPC273578
0.8581	High Similarity	NPC53722
0.8581	High Similarity	NPC478268
0.8581	High Similarity	NPC302610
0.8581	High Similarity	NPC201404
0.8581	High Similarity	NPC290714
0.8571	High Similarity	NPC149505
0.8562	High Similarity	NPC42797
0.8562	High Similarity	NPC249070
0.8553	High Similarity	NPC63061
0.8553	High Similarity	NPC474054
0.8544	High Similarity	NPC125495
0.8543	High Similarity	NPC121661
0.8543	High Similarity	NPC172171
0.8543	High Similarity	NPC73467
0.8543	High Similarity	NPC474036
0.8543	High Similarity	NPC239254
0.8543	High Similarity	NPC87883
0.8533	High Similarity	NPC474295
0.8533	High Similarity	NPC287124
0.8526	High Similarity	NPC149735
0.8493	Intermediate Similarity	NPC136750
0.8493	Intermediate Similarity	NPC266848
0.8491	Intermediate Similarity	NPC328122
0.8491	Intermediate Similarity	NPC125713
0.8491	Intermediate Similarity	NPC478269
0.8491	Intermediate Similarity	NPC474043
0.8487	Intermediate Similarity	NPC110763
0.8487	Intermediate Similarity	NPC189239
0.8487	Intermediate Similarity	NPC197352
0.8487	Intermediate Similarity	NPC166506
0.8477	Intermediate Similarity	NPC469630
0.8467	Intermediate Similarity	NPC312199
0.8462	Intermediate Similarity	NPC472612
0.8462	Intermediate Similarity	NPC472611
0.8462	Intermediate Similarity	NPC289967
0.8462	Intermediate Similarity	NPC220577
0.8447	Intermediate Similarity	NPC61141
0.8442	Intermediate Similarity	NPC93924
0.8442	Intermediate Similarity	NPC40654
0.8442	Intermediate Similarity	NPC262804
0.8442	Intermediate Similarity	NPC477879
0.8438	Intermediate Similarity	NPC96593
0.8431	Intermediate Similarity	NPC252286
0.8431	Intermediate Similarity	NPC154971
0.8428	Intermediate Similarity	NPC19947
0.8428	Intermediate Similarity	NPC207584
0.8425	Intermediate Similarity	NPC65183
0.8425	Intermediate Similarity	NPC261812
0.8425	Intermediate Similarity	NPC475856
0.8425	Intermediate Similarity	NPC72046
0.8425	Intermediate Similarity	NPC7744
0.8424	Intermediate Similarity	NPC469506
0.8421	Intermediate Similarity	NPC477701
0.8421	Intermediate Similarity	NPC141569
0.8421	Intermediate Similarity	NPC18211
0.8421	Intermediate Similarity	NPC166884
0.8421	Intermediate Similarity	NPC143092
0.8421	Intermediate Similarity	NPC475000
0.8411	Intermediate Similarity	NPC80326
0.8411	Intermediate Similarity	NPC184641
0.8411	Intermediate Similarity	NPC133934
0.8411	Intermediate Similarity	NPC184684
0.8411	Intermediate Similarity	NPC67467
0.8408	Intermediate Similarity	NPC245948
0.8405	Intermediate Similarity	NPC59516
0.8403	Intermediate Similarity	NPC207702
0.8403	Intermediate Similarity	NPC149008
0.8403	Intermediate Similarity	NPC283114
0.8387	Intermediate Similarity	NPC283839
0.8387	Intermediate Similarity	NPC90896
0.8385	Intermediate Similarity	NPC288149
0.8385	Intermediate Similarity	NPC478267
0.8378	Intermediate Similarity	NPC148893
0.8378	Intermediate Similarity	NPC25333
0.8378	Intermediate Similarity	NPC311430
0.8378	Intermediate Similarity	NPC224941
0.8378	Intermediate Similarity	NPC189474
0.8378	Intermediate Similarity	NPC49235
0.8378	Intermediate Similarity	NPC474139
0.8377	Intermediate Similarity	NPC104024
0.8377	Intermediate Similarity	NPC80230
0.8377	Intermediate Similarity	NPC101755
0.8377	Intermediate Similarity	NPC65574
0.8377	Intermediate Similarity	NPC304687
0.8373	Intermediate Similarity	NPC474568
0.8367	Intermediate Similarity	NPC1474
0.8366	Intermediate Similarity	NPC474158
0.8366	Intermediate Similarity	NPC477702
0.8365	Intermediate Similarity	NPC115123
0.8365	Intermediate Similarity	NPC32373
0.8365	Intermediate Similarity	NPC301897
0.8365	Intermediate Similarity	NPC11411
0.8365	Intermediate Similarity	NPC237946
0.8365	Intermediate Similarity	NPC239113
0.8356	Intermediate Similarity	NPC192255
0.8354	Intermediate Similarity	NPC475453

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 NPC475229 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	336
0.1-0.2	934
0.2-0.3	1712
0.3-0.4	2811
0.4-0.5	1768
0.5-0.6	955
0.6-0.7	539
0.7-0.8	87
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
0.8408	Intermediate Similarity	NPD37	Approved
0.8365	Intermediate Similarity	NPD4966	Approved
0.8365	Intermediate Similarity	NPD4967	Phase 2
0.8365	Intermediate Similarity	NPD4965	Approved
0.8323	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.8272	Intermediate Similarity	NPD7199	Phase 2
0.8261	Intermediate Similarity	NPD6234	Discontinued
0.8171	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.8024	Intermediate Similarity	NPD7228	Approved
0.7917	Intermediate Similarity	NPD3705	Approved
0.7836	Intermediate Similarity	NPD7240	Approved
0.7812	Intermediate Similarity	NPD1653	Approved
0.7785	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7765	Intermediate Similarity	NPD5844	Phase 1
0.7751	Intermediate Similarity	NPD7473	Discontinued
0.7679	Intermediate Similarity	NPD6232	Discontinued
0.7657	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7628	Intermediate Similarity	NPD7266	Discontinued
0.7602	Intermediate Similarity	NPD3818	Discontinued
0.759	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.756	Intermediate Similarity	NPD5494	Approved
0.7532	Intermediate Similarity	NPD6674	Discontinued
0.75	Intermediate Similarity	NPD3027	Phase 3
0.747	Intermediate Similarity	NPD7819	Suspended
0.7469	Intermediate Similarity	NPD1940	Clinical (unspecified phase)
0.743	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7429	Intermediate Similarity	NPD6559	Discontinued
0.7425	Intermediate Similarity	NPD3817	Phase 2
0.7414	Intermediate Similarity	NPD7074	Phase 3
0.7412	Intermediate Similarity	NPD8127	Discontinued
0.7368	Intermediate Similarity	NPD3018	Phase 2
0.7368	Intermediate Similarity	NPD7229	Phase 3
0.7365	Intermediate Similarity	NPD8455	Phase 2
0.7362	Intermediate Similarity	NPD7314	Clinical (unspecified phase)
0.7356	Intermediate Similarity	NPD7054	Approved
0.7355	Intermediate Similarity	NPD1613	Approved
0.7355	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7326	Intermediate Similarity	NPD7680	Approved
0.732	Intermediate Similarity	NPD4908	Phase 1
0.7314	Intermediate Similarity	NPD7472	Approved
0.7303	Intermediate Similarity	NPD7090	Clinical (unspecified phase)
0.7292	Intermediate Similarity	NPD5283	Phase 1
0.7288	Intermediate Similarity	NPD7808	Phase 3
0.7288	Intermediate Similarity	NPD7549	Discontinued
0.7278	Intermediate Similarity	NPD3748	Approved
0.7267	Intermediate Similarity	NPD2981	Phase 2
0.7262	Intermediate Similarity	NPD1465	Phase 2
0.7235	Intermediate Similarity	NPD7975	Clinical (unspecified phase)
0.7232	Intermediate Similarity	NPD7685	Pre-registration
0.723	Intermediate Similarity	NPD5691	Approved
0.7226	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7225	Intermediate Similarity	NPD3926	Phase 2
0.7219	Intermediate Similarity	NPD2983	Phase 2
0.7219	Intermediate Similarity	NPD2982	Phase 2
0.7208	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7204	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.7202	Intermediate Similarity	NPD1934	Approved
0.7193	Intermediate Similarity	NPD919	Approved
0.7191	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7184	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7184	Intermediate Similarity	NPD6166	Phase 2
0.7184	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7176	Intermediate Similarity	NPD7768	Phase 2
0.7175	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7151	Intermediate Similarity	NPD8313	Approved
0.7151	Intermediate Similarity	NPD8312	Approved
0.7143	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7135	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7135	Intermediate Similarity	NPD7251	Discontinued
0.7134	Intermediate Similarity	NPD4060	Phase 1
0.7125	Intermediate Similarity	NPD2438	Suspended
0.7117	Intermediate Similarity	NPD5084	Clinical (unspecified phase)
0.7115	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7095	Intermediate Similarity	NPD5536	Phase 2
0.709	Intermediate Similarity	NPD5006	Approved
0.709	Intermediate Similarity	NPD5005	Approved
0.7089	Intermediate Similarity	NPD1933	Approved
0.7088	Intermediate Similarity	NPD6843	Phase 3
0.7088	Intermediate Similarity	NPD6841	Approved
0.7088	Intermediate Similarity	NPD6842	Approved
0.7081	Intermediate Similarity	NPD5762	Approved
0.7081	Intermediate Similarity	NPD5763	Approved
0.7079	Intermediate Similarity	NPD6797	Phase 2
0.7076	Intermediate Similarity	NPD3882	Suspended
0.7065	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7055	Intermediate Similarity	NPD3750	Approved
0.7035	Intermediate Similarity	NPD7075	Discontinued
0.7029	Intermediate Similarity	NPD5242	Approved
0.7024	Intermediate Similarity	NPD6055	Clinical (unspecified phase)
0.7019	Intermediate Similarity	NPD2796	Approved
0.7018	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7018	Intermediate Similarity	NPD5353	Approved
0.7012	Intermediate Similarity	NPD5307	Clinical (unspecified phase)
0.7006	Intermediate Similarity	NPD3751	Discontinued
0.7	Intermediate Similarity	NPD7097	Phase 1
0.6994	Remote Similarity	NPD1652	Phase 2
0.6988	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6981	Remote Similarity	NPD5123	Clinical (unspecified phase)
0.6981	Remote Similarity	NPD6355	Discontinued
0.6981	Remote Similarity	NPD5124	Phase 1
0.6974	Remote Similarity	NPD1610	Phase 2
0.6971	Remote Similarity	NPD3787	Discontinued
0.6968	Remote Similarity	NPD4420	Approved
0.6966	Remote Similarity	NPD7804	Clinical (unspecified phase)
0.6959	Remote Similarity	NPD2801	Approved
0.6959	Remote Similarity	NPD8151	Discontinued
0.6954	Remote Similarity	NPD4626	Approved
0.6951	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6951	Remote Similarity	NPD7466	Approved
0.6943	Remote Similarity	NPD4625	Phase 3
0.6941	Remote Similarity	NPD7411	Suspended
0.6936	Remote Similarity	NPD3749	Approved
0.6933	Remote Similarity	NPD970	Clinical (unspecified phase)
0.6928	Remote Similarity	NPD6799	Approved
0.6923	Remote Similarity	NPD7458	Discontinued
0.6923	Remote Similarity	NPD2861	Phase 2
0.6923	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD8158	Clinical (unspecified phase)
0.6919	Remote Similarity	NPD5402	Approved
0.6918	Remote Similarity	NPD4140	Approved
0.6918	Remote Similarity	NPD2979	Phase 3
0.6914	Remote Similarity	NPD3539	Phase 1
0.6914	Remote Similarity	NPD6959	Discontinued
0.6914	Remote Similarity	NPD1247	Approved
0.6909	Remote Similarity	NPD6190	Approved
0.6901	Remote Similarity	NPD6801	Discontinued
0.6899	Remote Similarity	NPD6798	Discontinued
0.6893	Remote Similarity	NPD4481	Phase 3
0.6893	Remote Similarity	NPD7852	Clinical (unspecified phase)
0.6887	Remote Similarity	NPD1357	Approved
0.6886	Remote Similarity	NPD2532	Approved
0.6886	Remote Similarity	NPD2534	Approved
0.6886	Remote Similarity	NPD7446	Clinical (unspecified phase)
0.6886	Remote Similarity	NPD2533	Approved
0.6883	Remote Similarity	NPD5327	Phase 3
0.6882	Remote Similarity	NPD7028	Phase 2
0.6882	Remote Similarity	NPD4380	Phase 2
0.6882	Remote Similarity	NPD6599	Discontinued
0.6875	Remote Similarity	NPD3657	Discovery
0.6875	Remote Similarity	NPD1358	Approved
0.6872	Remote Similarity	NPD8156	Discontinued
0.6871	Remote Similarity	NPD5535	Approved
0.6871	Remote Similarity	NPD3540	Phase 1
0.6867	Remote Similarity	NPD6783	Clinical (unspecified phase)
0.6867	Remote Similarity	NPD7124	Phase 2
0.6863	Remote Similarity	NPD422	Phase 1
0.6863	Remote Similarity	NPD1611	Approved
0.6855	Remote Similarity	NPD8032	Phase 2
0.6852	Remote Similarity	NPD4108	Discontinued
0.6848	Remote Similarity	NPD8434	Phase 2
0.6848	Remote Similarity	NPD4109	Clinical (unspecified phase)
0.6848	Remote Similarity	NPD4110	Phase 3
0.6842	Remote Similarity	NPD5090	Approved
0.6842	Remote Similarity	NPD6386	Approved
0.6842	Remote Similarity	NPD6385	Approved
0.6842	Remote Similarity	NPD5089	Approved
0.6835	Remote Similarity	NPD7095	Approved
0.6826	Remote Similarity	NPD4357	Discontinued
0.6821	Remote Similarity	NPD6374	Clinical (unspecified phase)
0.6816	Remote Similarity	NPD8099	Discontinued
0.6816	Remote Similarity	NPD8252	Approved
0.6816	Remote Similarity	NPD8251	Approved
0.6813	Remote Similarity	NPD3619	Clinical (unspecified phase)
0.6813	Remote Similarity	NPD3620	Phase 2
0.6806	Remote Similarity	NPD3134	Approved
0.6805	Remote Similarity	NPD5403	Approved
0.6805	Remote Similarity	NPD920	Approved
0.6802	Remote Similarity	NPD3384	Approved
0.6802	Remote Similarity	NPD3382	Approved
0.6802	Remote Similarity	NPD7945	Clinical (unspecified phase)
0.6802	Remote Similarity	NPD3383	Approved
0.6792	Remote Similarity	NPD3764	Approved
0.6788	Remote Similarity	NPD5698	Clinical (unspecified phase)
0.6788	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6786	Remote Similarity	NPD5401	Approved
0.6774	Remote Similarity	NPD4379	Clinical (unspecified phase)
0.6774	Remote Similarity	NPD7235	Clinical (unspecified phase)
0.6772	Remote Similarity	NPD6832	Phase 2
0.6763	Remote Similarity	NPD5563	Clinical (unspecified phase)
0.6763	Remote Similarity	NPD4585	Approved
0.6753	Remote Similarity	NPD1281	Approved
0.6753	Remote Similarity	NPD1091	Approved
0.6752	Remote Similarity	NPD6917	Clinical (unspecified phase)
0.675	Remote Similarity	NPD6233	Phase 2
0.6747	Remote Similarity	NPD4628	Phase 3
0.6747	Remote Similarity	NPD7003	Approved
0.6747	Remote Similarity	NPD8166	Discontinued
0.6746	Remote Similarity	NPD6273	Approved
0.6744	Remote Similarity	NPD7615	Clinical (unspecified phase)
0.6743	Remote Similarity	NPD4055	Discovery
0.6726	Remote Similarity	NPD5297	Approved
0.6726	Remote Similarity	NPD1511	Approved
0.6725	Remote Similarity	NPD7261	Clinical (unspecified phase)
0.6725	Remote Similarity	NPD4005	Discontinued
0.6711	Remote Similarity	NPD1548	Phase 1
0.6707	Remote Similarity	NPD2935	Discontinued
0.6688	Remote Similarity	NPD3266	Approved
0.6688	Remote Similarity	NPD3267	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