NPASS Compound

Structure

NPC473736 OpenBabel07101719252D 45 48 0 0 1 0 0 0 0 0999 V2000 0.5236 -1.5426 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6562 -2.6287 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9050 -0.3749 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4360 4.0407 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.9869 -2.8792 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9811 3.5509 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.4767 -2.0308 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.4767 1.3626 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5485 -2.2503 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5772 -2.1224 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1448 -1.4731 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2024 -1.2174 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7699 -0.5681 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4238 0.4648 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4526 0.5926 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5379 -2.0308 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4360 2.0815 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2535 -0.9462 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.7512 -3.0036 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7987 -0.4403 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0481 -1.1825 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4360 1.1019 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2844 2.5713 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5175 -2.0308 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0778 1.4977 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2844 0.6121 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5379 -0.3341 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1327 1.1019 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1019 -1.4360 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.1327 2.0815 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0073 -1.1825 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5175 -0.3341 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4898 0.8484 0.0000 C 0 0 2 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 -1.6233 -3.9748 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.6741 2.2748 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.9811 0.6121 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.7772 0.5963 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.2844 3.5509 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.0073 -2.8792 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.9811 2.5713 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.9869 -1.1825 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.4971 1.3626 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.9740 -2.4072 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.1065 1.6255 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 18 1 0 0 0 0 2 19 1 0 0 0 0 4 39 1 0 0 0 0 5 40 1 0 0 0 0 6 41 1 0 0 0 0 7 42 1 0 0 0 0 8 43 1 0 0 0 0 9 10 2 0 0 0 0 9 11 1 0 0 0 0 10 12 1 0 0 0 0 11 13 2 0 0 0 0 12 20 2 0 0 0 0 13 20 1 0 0 0 0 14 15 2 0 0 0 0 14 20 1 0 0 0 0 15 25 1 0 0 0 0 16 21 2 0 0 0 0 16 24 1 0 0 0 0 17 22 2 0 0 0 0 17 23 1 0 0 0 0 18 29 1 0 0 0 0 18 34 1 1 0 0 0 19 35 2 0 0 0 0 19 44 1 0 0 0 0 21 27 1 0 0 0 0 21 29 1 0 0 0 0 22 26 1 0 0 0 0 22 33 1 0 0 0 0 23 30 2 0 0 0 0 23 39 1 0 0 0 0 24 31 2 0 0 0 0 24 40 1 0 0 0 0 25 36 2 0 0 0 0 25 45 1 0 0 0 0 26 27 1 0 0 0 0 26 28 2 0 0 0 0 27 32 2 0 0 0 0 28 30 1 0 0 0 0 28 37 1 0 0 0 0 29 44 1 6 0 0 0 30 41 1 0 0 0 0 31 32 1 0 0 0 0 31 42 1 0 0 0 0 32 43 1 0 0 0 0 33 34 1 1 0 0 0 33 45 1 0 0 0 0 34 3 1 6 0 0 0 34 38 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	622.24
Volume:	627.449
LogP:	3.776
LogD:	2.76
LogS:	-4.598
# Rotatable Bonds:	11
TPSA:	139.21
# H-Bond Aceptor:	11
# H-Bond Donor:	2
# Rings:	4
# Heavy Atoms:	11

MedChem Properties

QED Drug-Likeness Score:	0.234
Synthetic Accessibility Score:	4.195
Fsp3:	0.353
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	1
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.742
MDCK Permeability:	3.181515421601944e-05
Pgp-inhibitor:	0.998
Pgp-substrate:	0.023
Human Intestinal Absorption (HIA):	0.014
20% Bioavailability (F20%):	0.002
30% Bioavailability (F30%):	0.033

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.031
Plasma Protein Binding (PPB):	78.17119598388672%
Volume Distribution (VD):	0.618
Pgp-substrate:	21.306751251220703%

ADMET: Metabolism

CYP1A2-inhibitor:	0.044
CYP1A2-substrate:	0.966
CYP2C19-inhibitor:	0.58
CYP2C19-substrate:	0.827
CYP2C9-inhibitor:	0.908
CYP2C9-substrate:	0.913
CYP2D6-inhibitor:	0.136
CYP2D6-substrate:	0.327
CYP3A4-inhibitor:	0.727
CYP3A4-substrate:	0.903

ADMET: Excretion

Clearance (CL):	3.548
Half-life (T1/2):	0.122

ADMET: Toxicity

hERG Blockers:	0.093
Human Hepatotoxicity (H-HT):	0.331
Drug-inuced Liver Injury (DILI):	0.945
AMES Toxicity:	0.125
Rat Oral Acute Toxicity:	0.227
Maximum Recommended Daily Dose:	0.029
Skin Sensitization:	0.14
Carcinogencity:	0.024
Eye Corrosion:	0.003
Eye Irritation:	0.201
Respiratory Toxicity:	0.436

Download Data

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

Natural Product: NPC473736

Natural Product ID:	NPC473736
*Common Name:**	Kadangustin C
IUPAC Name:	n.a.
Synonyms:	Kadangustin C
Standard InCHIKey:	HCRDYSMLGNXTDO-FGMNBCQPSA-N
Standard InCHI:	InChI=1S/C34H38O11/c1-18-29(44-19(2)35)21-16-24(40-5)31(42-7)32(43-8)27(21)26-22(17-23(39-4)30(41-6)28(26)37)33(34(18,3)38)45-25(36)15-14-20-12-10-9-11-13-20/h9-18,29,33,37-38H,1-8H3/b15-14+/t18-,29-,33+,34-/m0/s1
SMILES:	CC1C(C2=CC(=C(C(=C2C3=C(C(=C(C=C3C(C1(C)O)OC(=O)C=CC4=CC=CC=C4)OC)OC)O)OC)OC)OC)OC(=O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL450645
PubChem CID:	24862692
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	=	190270.0	nM	PMID[470191]
NPT24	Organism	Human immunodeficiency virus 1	Human immunodeficiency virus 1	EC50	=	38340.0	nM	PMID[470191]
NPT2	Others	Unspecified		Ratio	=	4.96	n.a.	PMID[470191]

☑ 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 NPC473736 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	354
0.1-0.2	1430
0.2-0.3	3452
0.3-0.4	8495
0.4-0.5	10087
0.5-0.6	3702
0.6-0.7	6309
0.7-0.8	7506
0.8-0.85	1105
0.85-0.9	209
0.9-0.95	40
0.95-1	8

Similarity Score	Similarity Level	Natural Product ID
0.9932	High Similarity	NPC475141
0.9592	High Similarity	NPC470916
0.9524	High Similarity	NPC474347
0.9524	High Similarity	NPC474393
0.9481	High Similarity	NPC291977
0.9474	High Similarity	NPC215400
0.9474	High Similarity	NPC230531
0.9416	High Similarity	NPC42797
0.9416	High Similarity	NPC473445
0.9388	High Similarity	NPC295297
0.9324	High Similarity	NPC252402
0.9324	High Similarity	NPC102934
0.932	High Similarity	NPC474054
0.9315	High Similarity	NPC87883
0.9281	High Similarity	NPC475592
0.9272	High Similarity	NPC149735
0.9247	High Similarity	NPC469630
0.915	High Similarity	NPC476065
0.9139	High Similarity	NPC477379
0.9079	High Similarity	NPC475229
0.9079	High Similarity	NPC477378
0.9073	High Similarity	NPC477381
0.9032	High Similarity	NPC125495
0.902	High Similarity	NPC77237
0.902	High Similarity	NPC477377
0.902	High Similarity	NPC126405
0.902	High Similarity	NPC297271
0.902	High Similarity	NPC53669
0.902	High Similarity	NPC16791
0.902	High Similarity	NPC217708
0.902	High Similarity	NPC308739
0.9013	High Similarity	NPC224472
0.9	High Similarity	NPC137352
0.9	High Similarity	NPC183083
0.9	High Similarity	NPC88557
0.8973	High Similarity	NPC471183
0.8954	High Similarity	NPC471154
0.8938	High Similarity	NPC311912
0.8933	High Similarity	NPC268515
0.8933	High Similarity	NPC40222
0.8924	High Similarity	NPC249070
0.8919	High Similarity	NPC67467
0.8904	High Similarity	NPC865
0.8896	High Similarity	NPC474606
0.8896	High Similarity	NPC24562
0.8889	High Similarity	NPC475756
0.8882	High Similarity	NPC475250
0.8875	High Similarity	NPC83049
0.8875	High Similarity	NPC118162
0.8875	High Similarity	NPC320471
0.8854	High Similarity	NPC328122
0.8839	High Similarity	NPC198461
0.8836	High Similarity	NPC133025
0.8831	High Similarity	NPC476434
0.8816	High Similarity	NPC477879
0.8782	High Similarity	NPC238834
0.8776	High Similarity	NPC86605
0.8776	High Similarity	NPC3072
0.8776	High Similarity	NPC46277
0.8776	High Similarity	NPC301765
0.8776	High Similarity	NPC156948
0.8774	High Similarity	NPC115203
0.8774	High Similarity	NPC470769
0.8767	High Similarity	NPC55239
0.8767	High Similarity	NPC180602
0.8767	High Similarity	NPC240279
0.8767	High Similarity	NPC214853
0.8758	High Similarity	NPC477376
0.8758	High Similarity	NPC322426
0.8758	High Similarity	NPC477374
0.875	High Similarity	NPC178129
0.8726	High Similarity	NPC473323
0.8718	High Similarity	NPC312763
0.8712	High Similarity	NPC477883
0.871	High Similarity	NPC120774
0.871	High Similarity	NPC264875
0.871	High Similarity	NPC163598
0.8707	High Similarity	NPC120852
0.8704	High Similarity	NPC79322
0.8701	High Similarity	NPC316989
0.8701	High Similarity	NPC24425
0.8699	High Similarity	NPC7515
0.8699	High Similarity	NPC56764
0.8699	High Similarity	NPC276026
0.8699	High Similarity	NPC555
0.8699	High Similarity	NPC469659
0.8699	High Similarity	NPC188378
0.8699	High Similarity	NPC289258
0.8699	High Similarity	NPC206737
0.8693	High Similarity	NPC316676
0.8693	High Similarity	NPC187398
0.8693	High Similarity	NPC252281
0.8693	High Similarity	NPC477375
0.8693	High Similarity	NPC325720
0.8693	High Similarity	NPC327352
0.8693	High Similarity	NPC476348
0.8693	High Similarity	NPC198129
0.8671	High Similarity	NPC470827
0.8658	High Similarity	NPC472092
0.8658	High Similarity	NPC291101
0.8658	High Similarity	NPC472091
0.8658	High Similarity	NPC106055
0.8658	High Similarity	NPC472090
0.8658	High Similarity	NPC266197
0.8658	High Similarity	NPC110699
0.8636	High Similarity	NPC30688
0.8636	High Similarity	NPC321657
0.8636	High Similarity	NPC318373
0.8636	High Similarity	NPC176903
0.8627	High Similarity	NPC97937
0.8627	High Similarity	NPC320671
0.8627	High Similarity	NPC170239
0.8627	High Similarity	NPC327412
0.8627	High Similarity	NPC476347
0.8627	High Similarity	NPC320970
0.8627	High Similarity	NPC275125
0.8627	High Similarity	NPC328567
0.8625	High Similarity	NPC319749
0.8618	High Similarity	NPC143120
0.8618	High Similarity	NPC274960
0.8618	High Similarity	NPC473909
0.8616	High Similarity	NPC470828
0.8608	High Similarity	NPC469474
0.8606	High Similarity	NPC477881
0.8599	High Similarity	NPC268484
0.8599	High Similarity	NPC7178
0.8599	High Similarity	NPC62903
0.8591	High Similarity	NPC6300
0.8591	High Similarity	NPC230124
0.8591	High Similarity	NPC184613
0.8591	High Similarity	NPC114171
0.8591	High Similarity	NPC22517
0.859	High Similarity	NPC478268
0.8581	High Similarity	NPC471988
0.8581	High Similarity	NPC120426
0.8581	High Similarity	NPC294522
0.8581	High Similarity	NPC21184
0.8581	High Similarity	NPC202846
0.8581	High Similarity	NPC205727
0.8581	High Similarity	NPC143139
0.8581	High Similarity	NPC473989
0.8571	High Similarity	NPC135127
0.8562	High Similarity	NPC301089
0.8562	High Similarity	NPC324492
0.8562	High Similarity	NPC317053
0.8562	High Similarity	NPC260397
0.8562	High Similarity	NPC102256
0.8553	High Similarity	NPC326144
0.8553	High Similarity	NPC73467
0.8553	High Similarity	NPC121661
0.8553	High Similarity	NPC471824
0.8544	High Similarity	NPC142479
0.8544	High Similarity	NPC155015
0.8543	High Similarity	NPC472087
0.8543	High Similarity	NPC472088
0.8535	High Similarity	NPC178574
0.8535	High Similarity	NPC65591
0.8535	High Similarity	NPC223720
0.8533	High Similarity	NPC308768
0.8533	High Similarity	NPC12668
0.8516	High Similarity	NPC113790
0.8516	High Similarity	NPC476969
0.8516	High Similarity	NPC106138
0.8516	High Similarity	NPC85141
0.8514	High Similarity	NPC294884
0.8514	High Similarity	NPC10314
0.8514	High Similarity	NPC69029
0.8514	High Similarity	NPC108198
0.8514	High Similarity	NPC158142
0.8514	High Similarity	NPC200557
0.8514	High Similarity	NPC313081
0.8506	High Similarity	NPC262297
0.85	High Similarity	NPC478269
0.8497	Intermediate Similarity	NPC197352
0.8497	Intermediate Similarity	NPC318286
0.8497	Intermediate Similarity	NPC166506
0.8497	Intermediate Similarity	NPC181615
0.8497	Intermediate Similarity	NPC110763
0.8497	Intermediate Similarity	NPC189239
0.8497	Intermediate Similarity	NPC327651
0.8497	Intermediate Similarity	NPC125617
0.8497	Intermediate Similarity	NPC163898
0.8493	Intermediate Similarity	NPC141493
0.8493	Intermediate Similarity	NPC184928
0.8491	Intermediate Similarity	NPC29727
0.8487	Intermediate Similarity	NPC110067
0.8487	Intermediate Similarity	NPC34245
0.8487	Intermediate Similarity	NPC91492
0.8487	Intermediate Similarity	NPC218510
0.8487	Intermediate Similarity	NPC6568
0.8487	Intermediate Similarity	NPC76415
0.8487	Intermediate Similarity	NPC7439
0.8487	Intermediate Similarity	NPC256555
0.8485	Intermediate Similarity	NPC180768
0.8481	Intermediate Similarity	NPC473425
0.8477	Intermediate Similarity	NPC472089
0.8477	Intermediate Similarity	NPC178054
0.8471	Intermediate Similarity	NPC289967
0.8471	Intermediate Similarity	NPC472611
0.8471	Intermediate Similarity	NPC472612

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 NPC473736 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	302
0.1-0.2	887
0.2-0.3	1734
0.3-0.4	2704
0.4-0.5	1814
0.5-0.6	968
0.6-0.7	598
0.7-0.8	133
0.8-0.85	10
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8272	Intermediate Similarity	NPD6234	Discontinued
0.8261	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.8231	Intermediate Similarity	NPD3027	Phase 3
0.8193	Intermediate Similarity	NPD7473	Discontinued
0.8121	Intermediate Similarity	NPD6232	Discontinued
0.8095	Intermediate Similarity	NPD5844	Phase 1
0.8075	Intermediate Similarity	NPD37	Approved
0.8067	Intermediate Similarity	NPD1613	Approved
0.8067	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.805	Intermediate Similarity	NPD1653	Approved
0.8037	Intermediate Similarity	NPD4967	Phase 2
0.8037	Intermediate Similarity	NPD4966	Approved
0.8037	Intermediate Similarity	NPD4965	Approved
0.8036	Intermediate Similarity	NPD7228	Approved
0.7952	Intermediate Similarity	NPD7199	Phase 2
0.7919	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7914	Intermediate Similarity	NPD1465	Phase 2
0.7874	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7871	Intermediate Similarity	NPD7266	Discontinued
0.7857	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7853	Intermediate Similarity	NPD1934	Approved
0.7852	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7811	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7811	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7811	Intermediate Similarity	NPD6166	Phase 2
0.78	Intermediate Similarity	NPD4908	Phase 1
0.7791	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.774	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7712	Intermediate Similarity	NPD4060	Phase 1
0.7701	Intermediate Similarity	NPD7549	Discontinued
0.7697	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7697	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7697	Intermediate Similarity	NPD7819	Suspended
0.7673	Intermediate Similarity	NPD6190	Approved
0.7651	Intermediate Similarity	NPD3817	Phase 2
0.763	Intermediate Similarity	NPD7074	Phase 3
0.7616	Intermediate Similarity	NPD3818	Discontinued
0.7605	Intermediate Similarity	NPD7768	Phase 2
0.759	Intermediate Similarity	NPD2801	Approved
0.7572	Intermediate Similarity	NPD7054	Approved
0.756	Intermediate Similarity	NPD7075	Discontinued
0.7546	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7543	Intermediate Similarity	NPD7240	Approved
0.7529	Intermediate Similarity	NPD8127	Discontinued
0.7529	Intermediate Similarity	NPD7472	Approved
0.7516	Intermediate Similarity	NPD4625	Phase 3
0.75	Intermediate Similarity	NPD3750	Approved
0.75	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD3882	Suspended
0.7469	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7467	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.745	Intermediate Similarity	NPD1610	Phase 2
0.7443	Intermediate Similarity	NPD7685	Pre-registration
0.744	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7438	Intermediate Similarity	NPD6674	Discontinued
0.7436	Intermediate Similarity	NPD5124	Phase 1
0.7436	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.741	Intermediate Similarity	NPD4380	Phase 2
0.7401	Intermediate Similarity	NPD7808	Phase 3
0.7401	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7391	Intermediate Similarity	NPD8166	Discontinued
0.7386	Intermediate Similarity	NPD3018	Phase 2
0.7384	Intermediate Similarity	NPD7229	Phase 3
0.7381	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7378	Intermediate Similarity	NPD1940	Clinical (unspecified phase)
0.7378	Intermediate Similarity	NPD7314	Clinical (unspecified phase)
0.7375	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7372	Intermediate Similarity	NPD3620	Phase 2
0.7372	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.7362	Intermediate Similarity	NPD1511	Approved
0.7355	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7353	Intermediate Similarity	NPD7975	Clinical (unspecified phase)
0.7345	Intermediate Similarity	NPD7251	Discontinued
0.7345	Intermediate Similarity	NPD6559	Discontinued
0.734	Intermediate Similarity	NPD7680	Approved
0.7333	Intermediate Similarity	NPD422	Phase 1
0.7329	Intermediate Similarity	NPD1652	Phase 2
0.7326	Intermediate Similarity	NPD6959	Discontinued
0.7325	Intermediate Similarity	NPD230	Phase 1
0.7318	Intermediate Similarity	NPD7090	Clinical (unspecified phase)
0.7312	Intermediate Similarity	NPD5762	Approved
0.7312	Intermediate Similarity	NPD5763	Approved
0.7299	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.729	Intermediate Similarity	NPD7095	Approved
0.7288	Intermediate Similarity	NPD6797	Phase 2
0.7278	Intermediate Similarity	NPD8455	Phase 2
0.7273	Intermediate Similarity	NPD1512	Approved
0.7273	Intermediate Similarity	NPD2861	Phase 2
0.7268	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7267	Intermediate Similarity	NPD5494	Approved
0.7263	Intermediate Similarity	NPD8313	Approved
0.7263	Intermediate Similarity	NPD8312	Approved
0.7262	Intermediate Similarity	NPD7411	Suspended
0.7251	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7251	Intermediate Similarity	NPD3749	Approved
0.7246	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7244	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7244	Intermediate Similarity	NPD6798	Discontinued
0.7237	Intermediate Similarity	NPD2983	Phase 2
0.7237	Intermediate Similarity	NPD4749	Approved
0.7237	Intermediate Similarity	NPD2982	Phase 2
0.7235	Intermediate Similarity	NPD5402	Approved
0.7219	Intermediate Similarity	NPD6801	Discontinued
0.7219	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.7216	Intermediate Similarity	NPD3751	Discontinued
0.7215	Intermediate Similarity	NPD6355	Discontinued
0.7212	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.72	Intermediate Similarity	NPD4626	Approved
0.7192	Intermediate Similarity	NPD5283	Phase 1
0.7188	Intermediate Similarity	NPD3748	Approved
0.7181	Intermediate Similarity	NPD1548	Phase 1
0.7178	Intermediate Similarity	NPD4628	Phase 3
0.7171	Intermediate Similarity	NPD2981	Phase 2
0.7152	Intermediate Similarity	NPD6799	Approved
0.7143	Intermediate Similarity	NPD2935	Discontinued
0.7143	Intermediate Similarity	NPD8434	Phase 2
0.7143	Intermediate Similarity	NPD6099	Approved
0.7143	Intermediate Similarity	NPD6100	Approved
0.7134	Intermediate Similarity	NPD3764	Approved
0.7133	Intermediate Similarity	NPD5691	Approved
0.7127	Intermediate Similarity	NPD8053	Approved
0.7127	Intermediate Similarity	NPD8054	Approved
0.7126	Intermediate Similarity	NPD5403	Approved
0.7125	Intermediate Similarity	NPD7097	Phase 1
0.7117	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7117	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7108	Intermediate Similarity	NPD2533	Approved
0.7108	Intermediate Similarity	NPD7446	Clinical (unspecified phase)
0.7108	Intermediate Similarity	NPD2532	Approved
0.7108	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7108	Intermediate Similarity	NPD2534	Approved
0.7105	Intermediate Similarity	NPD3705	Approved
0.7101	Intermediate Similarity	NPD6599	Discontinued
0.7099	Intermediate Similarity	NPD2029	Clinical (unspecified phase)
0.7097	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7089	Intermediate Similarity	NPD6233	Phase 2
0.7086	Intermediate Similarity	NPD3787	Discontinued
0.7081	Intermediate Similarity	NPD1510	Phase 2
0.7079	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7073	Intermediate Similarity	NPD7003	Approved
0.7062	Intermediate Similarity	NPD8151	Discontinued
0.7059	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7055	Intermediate Similarity	NPD1549	Phase 2
0.7055	Intermediate Similarity	NPD228	Approved
0.7049	Intermediate Similarity	NPD8150	Discontinued
0.7048	Intermediate Similarity	NPD4357	Discontinued
0.7044	Intermediate Similarity	NPD4140	Approved
0.7037	Intermediate Similarity	NPD2438	Suspended
0.7032	Intermediate Similarity	NPD2797	Approved
0.7013	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7011	Intermediate Similarity	NPD6843	Phase 3
0.7011	Intermediate Similarity	NPD7906	Approved
0.7011	Intermediate Similarity	NPD6841	Approved
0.7011	Intermediate Similarity	NPD6842	Approved
0.7006	Intermediate Similarity	NPD5401	Approved
0.7006	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7006	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD5536	Phase 2
0.6994	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6994	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.6971	Remote Similarity	NPD6746	Phase 2
0.697	Remote Similarity	NPD4109	Clinical (unspecified phase)
0.697	Remote Similarity	NPD4110	Phase 3
0.6959	Remote Similarity	NPD5090	Approved
0.6959	Remote Similarity	NPD5089	Approved
0.6949	Remote Similarity	NPD5242	Approved
0.6949	Remote Similarity	NPD3926	Phase 2
0.6941	Remote Similarity	NPD4005	Discontinued
0.6941	Remote Similarity	NPD3226	Approved
0.6937	Remote Similarity	NPD1240	Approved
0.6936	Remote Similarity	NPD5353	Approved
0.6933	Remote Similarity	NPD2796	Approved
0.6933	Remote Similarity	NPD1551	Phase 2
0.6928	Remote Similarity	NPD3496	Discontinued
0.6928	Remote Similarity	NPD5307	Clinical (unspecified phase)
0.6918	Remote Similarity	NPD3022	Approved
0.6918	Remote Similarity	NPD3268	Approved
0.6918	Remote Similarity	NPD3021	Approved
0.6914	Remote Similarity	NPD919	Approved
0.6905	Remote Similarity	NPD4160	Clinical (unspecified phase)
0.6905	Remote Similarity	NPD7447	Phase 1
0.6894	Remote Similarity	NPD447	Suspended
0.6894	Remote Similarity	NPD4340	Discontinued
0.6894	Remote Similarity	NPD5735	Approved
0.689	Remote Similarity	NPD3540	Phase 1
0.6871	Remote Similarity	NPD7033	Discontinued
0.6867	Remote Similarity	NPD7982	Clinical (unspecified phase)
0.6864	Remote Similarity	NPD6273	Approved
0.6859	Remote Similarity	NPD1283	Approved
0.6859	Remote Similarity	NPD8651	Approved
0.6857	Remote Similarity	NPD4055	Discovery
0.6852	Remote Similarity	NPD1607	Approved
0.6852	Remote Similarity	NPD6653	Approved
0.6845	Remote Similarity	NPD7040	Clinical (unspecified phase)
0.6845	Remote Similarity	NPD7041	Phase 2
0.6845	Remote Similarity	NPD7212	Phase 2
0.6845	Remote Similarity	NPD7213	Phase 3
0.6842	Remote Similarity	NPD8158	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD7458	Discontinued
0.6835	Remote Similarity	NPD5736	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