NPASS Compound

Structure

NPC473445 OpenBabel07101718282D 42 45 0 0 1 0 0 0 0 0999 V2000 -2.8916 -3.0629 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1127 -1.8418 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7300 -3.7113 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9846 2.7442 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5416 -1.4674 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0715 2.7442 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5416 -0.4891 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8472 2.4457 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.6002 0.4128 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.8241 1.0083 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.4725 -0.5571 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.9203 0.6340 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.5687 -0.9315 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0063 1.0498 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -1.9565 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5172 -2.1591 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.2089 -1.4674 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.7601 -3.8390 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.7926 -0.3359 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5172 0.2026 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8472 -1.4674 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5172 1.8970 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8472 -1.4674 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5389 0.2026 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8472 -0.4891 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0498 1.0498 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5389 -2.1591 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.2089 -0.4891 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.5389 1.8970 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8472 -0.4891 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.8888 -0.7103 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3857 -4.7428 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0715 1.0498 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.7611 -1.6802 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.0063 2.7442 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.6944 -1.9565 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.0498 2.7442 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.6944 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 1.9565 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.1646 -3.0629 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.1127 -0.1148 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3 18 1 0 0 0 0 4 36 1 0 0 0 0 5 37 1 0 0 0 0 6 38 1 0 0 0 0 7 39 1 0 0 0 0 8 40 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 19 2 0 0 0 0 13 19 1 0 0 0 0 14 20 2 0 0 0 0 14 22 1 0 0 0 0 15 21 2 0 0 0 0 15 23 1 0 0 0 0 16 1 1 6 0 0 0 16 17 1 0 0 0 0 16 27 1 0 0 0 0 17 2 1 6 0 0 0 17 28 1 0 0 0 0 18 33 2 0 0 0 0 18 41 1 0 0 0 0 19 32 1 0 0 0 0 20 24 1 0 0 0 0 20 28 1 0 0 0 0 21 25 1 0 0 0 0 21 27 1 0 0 0 0 22 29 2 0 0 0 0 22 36 1 0 0 0 0 23 30 2 0 0 0 0 23 37 1 0 0 0 0 24 25 1 0 0 0 0 24 26 2 0 0 0 0 25 31 2 0 0 0 0 26 29 1 0 0 0 0 26 34 1 0 0 0 0 27 41 1 1 0 0 0 28 42 1 6 0 0 0 29 38 1 0 0 0 0 30 31 1 0 0 0 0 30 39 1 0 0 0 0 31 40 1 0 0 0 0 32 35 2 0 0 0 0 32 42 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	580.23
Volume:	586.703
LogP:	4.507
LogD:	3.405
LogS:	-4.661
# Rotatable Bonds:	10
TPSA:	118.98
# H-Bond Aceptor:	10
# H-Bond Donor:	1
# Rings:	4
# Heavy Atoms:	10

MedChem Properties

QED Drug-Likeness Score:	0.323
Synthetic Accessibility Score:	4.004
Fsp3:	0.375
Lipinski Rule-of-5:	Accepted
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:	-4.803
MDCK Permeability:	3.771608680835925e-05
Pgp-inhibitor:	0.998
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.014
20% Bioavailability (F20%):	0.0
30% Bioavailability (F30%):	0.026

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.03
Plasma Protein Binding (PPB):	75.62522888183594%
Volume Distribution (VD):	0.469
Pgp-substrate:	23.93828582763672%

ADMET: Metabolism

CYP1A2-inhibitor:	0.024
CYP1A2-substrate:	0.956
CYP2C19-inhibitor:	0.897
CYP2C19-substrate:	0.907
CYP2C9-inhibitor:	0.92
CYP2C9-substrate:	0.803
CYP2D6-inhibitor:	0.012
CYP2D6-substrate:	0.366
CYP3A4-inhibitor:	0.619
CYP3A4-substrate:	0.915

ADMET: Excretion

Clearance (CL):	5.054
Half-life (T1/2):	0.15

ADMET: Toxicity

hERG Blockers:	0.389
Human Hepatotoxicity (H-HT):	0.07
Drug-inuced Liver Injury (DILI):	0.972
AMES Toxicity:	0.052
Rat Oral Acute Toxicity:	0.173
Maximum Recommended Daily Dose:	0.017
Skin Sensitization:	0.071
Carcinogencity:	0.021
Eye Corrosion:	0.003
Eye Irritation:	0.089
Respiratory Toxicity:	0.425

Download Data

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

Natural Product: NPC473445

Natural Product ID:	NPC473445
*Common Name:**	Kadangustin E
IUPAC Name:	n.a.
Synonyms:	Kadangustin E
Standard InCHIKey:	ZGVQUOCWHUQALV-AOASNDSOSA-N
Standard InCHI:	InChI=1S/C32H36O10/c1-16-17(2)28(42-32(35)19-12-10-9-11-13-19)20-14-22(36-4)29(38-6)26(34)24(20)25-21(27(16)41-18(3)33)15-23(37-5)30(39-7)31(25)40-8/h9-17,27-28,34H,1-8H3/t16-,17+,27+,28+/m1/s1
SMILES:	COc1cc2[C@@H](OC(=O)c3ccccc3)[C@@H](C)[C@@H](C)[C@@H](c3c(c2c(c1OC)O)c(OC)c(c(c3)OC)OC)OC(=O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL435985
PubChem CID:	24862694
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	=	138260.0	nM	PMID[558134]
NPT24	Organism	Human immunodeficiency virus 1	Human immunodeficiency virus 1	EC50	=	60840.0	nM	PMID[558134]
NPT2	Others	Unspecified		Ratio	=	2.27	n.a.	PMID[558134]

☑ 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 NPC473445 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	367
0.1-0.2	1411
0.2-0.3	3191
0.3-0.4	8062
0.4-0.5	10520
0.5-0.6	3275
0.6-0.7	5014
0.7-0.8	7970
0.8-0.85	2462
0.85-0.9	366
0.9-0.95	51
0.95-1	8

Similarity Score	Similarity Level	Natural Product ID
0.9935	High Similarity	NPC291977
0.987	High Similarity	NPC42797
0.9497	High Similarity	NPC311912
0.949	High Similarity	NPC249070
0.9477	High Similarity	NPC475141
0.9437	High Similarity	NPC88557
0.9416	High Similarity	NPC473736
0.9313	High Similarity	NPC320471
0.9313	High Similarity	NPC118162
0.9313	High Similarity	NPC83049
0.9299	High Similarity	NPC328122
0.9216	High Similarity	NPC474393
0.9216	High Similarity	NPC474347
0.9182	High Similarity	NPC319749
0.9156	High Similarity	NPC470916
0.9136	High Similarity	NPC79322
0.9057	High Similarity	NPC230531
0.9057	High Similarity	NPC215400
0.9038	High Similarity	NPC476434
0.903	High Similarity	NPC477881
0.9024	High Similarity	NPC180768
0.9012	High Similarity	NPC477884
0.9006	High Similarity	NPC476372
0.9006	High Similarity	NPC476371
0.9	High Similarity	NPC53889
0.9	High Similarity	NPC24627
0.8981	High Similarity	NPC474656
0.8981	High Similarity	NPC149735
0.897	High Similarity	NPC469506
0.8961	High Similarity	NPC295297
0.8944	High Similarity	NPC191352
0.8944	High Similarity	NPC258322
0.8938	High Similarity	NPC87317
0.8931	High Similarity	NPC469474
0.8931	High Similarity	NPC227062
0.8917	High Similarity	NPC267091
0.8917	High Similarity	NPC272566
0.8909	High Similarity	NPC477883
0.8903	High Similarity	NPC102934
0.8903	High Similarity	NPC252402
0.8896	High Similarity	NPC474054
0.8889	High Similarity	NPC87883
0.8889	High Similarity	NPC280778
0.8882	High Similarity	NPC476373
0.8875	High Similarity	NPC114179
0.8875	High Similarity	NPC68324
0.8875	High Similarity	NPC156818
0.8875	High Similarity	NPC143328
0.8875	High Similarity	NPC475592
0.8875	High Similarity	NPC160512
0.8875	High Similarity	NPC289322
0.8875	High Similarity	NPC38779
0.8869	High Similarity	NPC477882
0.8869	High Similarity	NPC477880
0.8868	High Similarity	NPC476065
0.8868	High Similarity	NPC238834
0.8854	High Similarity	NPC243891
0.8854	High Similarity	NPC477379
0.8848	High Similarity	NPC476279
0.8827	High Similarity	NPC216916
0.8824	High Similarity	NPC469630
0.8812	High Similarity	NPC104983
0.8812	High Similarity	NPC88803
0.8812	High Similarity	NPC291948
0.8812	High Similarity	NPC300845
0.8812	High Similarity	NPC250436
0.881	High Similarity	NPC472723
0.881	High Similarity	NPC67629
0.881	High Similarity	NPC79736
0.8805	High Similarity	NPC116850
0.8805	High Similarity	NPC291510
0.8805	High Similarity	NPC197188
0.8805	High Similarity	NPC144801
0.8805	High Similarity	NPC43872
0.8805	High Similarity	NPC238672
0.8795	High Similarity	NPC476365
0.879	High Similarity	NPC477381
0.8765	High Similarity	NPC301089
0.8765	High Similarity	NPC24164
0.8758	High Similarity	NPC35598
0.8758	High Similarity	NPC222689
0.8757	High Similarity	NPC267549
0.8742	High Similarity	NPC474606
0.8742	High Similarity	NPC178574
0.8742	High Similarity	NPC65591
0.8742	High Similarity	NPC295646
0.8742	High Similarity	NPC477377
0.8735	High Similarity	NPC117911
0.8727	High Similarity	NPC43065
0.872	High Similarity	NPC45943
0.8712	High Similarity	NPC469889
0.8704	High Similarity	NPC40702
0.8704	High Similarity	NPC267627
0.8704	High Similarity	NPC37502
0.8696	High Similarity	NPC318432
0.869	High Similarity	NPC98583
0.8688	High Similarity	NPC469888
0.8679	High Similarity	NPC78505
0.8679	High Similarity	NPC75695
0.8679	High Similarity	NPC228662
0.8679	High Similarity	NPC475229
0.8679	High Similarity	NPC477378
0.8679	High Similarity	NPC471154
0.8667	High Similarity	NPC471788
0.8667	High Similarity	NPC142614
0.8662	High Similarity	NPC477879
0.8659	High Similarity	NPC149389
0.8659	High Similarity	NPC201800
0.8659	High Similarity	NPC472964
0.865	High Similarity	NPC292415
0.8642	High Similarity	NPC477885
0.8642	High Similarity	NPC125495
0.8642	High Similarity	NPC247713
0.8634	High Similarity	NPC145425
0.8634	High Similarity	NPC16082
0.8634	High Similarity	NPC476642
0.8634	High Similarity	NPC82592
0.8631	High Similarity	NPC178737
0.8631	High Similarity	NPC476370
0.8631	High Similarity	NPC471181
0.8631	High Similarity	NPC100251
0.8625	High Similarity	NPC297271
0.8625	High Similarity	NPC24562
0.8625	High Similarity	NPC199773
0.8625	High Similarity	NPC53669
0.8625	High Similarity	NPC126405
0.8625	High Similarity	NPC308739
0.8625	High Similarity	NPC217708
0.8625	High Similarity	NPC16791
0.8625	High Similarity	NPC77237
0.8616	High Similarity	NPC475756
0.8614	High Similarity	NPC474042
0.8614	High Similarity	NPC174734
0.8606	High Similarity	NPC67959
0.8606	High Similarity	NPC469518
0.8606	High Similarity	NPC134047
0.8606	High Similarity	NPC121290
0.8606	High Similarity	NPC272750
0.8606	High Similarity	NPC469475
0.8606	High Similarity	NPC223006
0.8606	High Similarity	NPC173729
0.8599	High Similarity	NPC183083
0.8599	High Similarity	NPC137352
0.8598	High Similarity	NPC158188
0.8598	High Similarity	NPC473106
0.8598	High Similarity	NPC103201
0.8596	High Similarity	NPC80956
0.8589	High Similarity	NPC325122
0.8588	High Similarity	NPC196771
0.8588	High Similarity	NPC297574
0.858	High Similarity	NPC165483
0.858	High Similarity	NPC54928
0.858	High Similarity	NPC477380
0.858	High Similarity	NPC150227
0.858	High Similarity	NPC476374
0.8571	High Similarity	NPC125487
0.8571	High Similarity	NPC298802
0.8571	High Similarity	NPC281477
0.8571	High Similarity	NPC281703
0.8563	High Similarity	NPC473818
0.8562	High Similarity	NPC471183
0.8562	High Similarity	NPC204350
0.8553	High Similarity	NPC316989
0.8553	High Similarity	NPC473091
0.8547	High Similarity	NPC8940
0.8545	High Similarity	NPC469512
0.8545	High Similarity	NPC144557
0.8545	High Similarity	NPC14030
0.8545	High Similarity	NPC291957
0.8545	High Similarity	NPC174311
0.8544	High Similarity	NPC81835
0.8537	High Similarity	NPC472055
0.8537	High Similarity	NPC36217
0.8537	High Similarity	NPC299436
0.8537	High Similarity	NPC472902
0.8535	High Similarity	NPC268515
0.8535	High Similarity	NPC40222
0.8528	High Similarity	NPC299520
0.8528	High Similarity	NPC296044
0.8528	High Similarity	NPC472963
0.8528	High Similarity	NPC472860
0.8528	High Similarity	NPC129684
0.8528	High Similarity	NPC190020
0.8528	High Similarity	NPC84935
0.8528	High Similarity	NPC77679
0.8528	High Similarity	NPC108456
0.8528	High Similarity	NPC167098
0.8526	High Similarity	NPC16353
0.8521	High Similarity	NPC65333
0.8521	High Similarity	NPC4200
0.8519	High Similarity	NPC38898
0.8519	High Similarity	NPC79998
0.8519	High Similarity	NPC203757
0.8519	High Similarity	NPC67396
0.8519	High Similarity	NPC286052
0.8519	High Similarity	NPC222185
0.8519	High Similarity	NPC20541
0.8519	High Similarity	NPC199926
0.8516	High Similarity	NPC67467
0.8512	High Similarity	NPC188079

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 NPC473445 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	310
0.1-0.2	905
0.2-0.3	1618
0.3-0.4	2565
0.4-0.5	1891
0.5-0.6	1086
0.6-0.7	570
0.7-0.8	173
0.8-0.85	25
0.85-0.9	6
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8812	High Similarity	NPD4868	Clinical (unspecified phase)
0.8727	High Similarity	NPD7473	Discontinued
0.8659	High Similarity	NPD6232	Discontinued
0.8623	High Similarity	NPD5844	Phase 1
0.8476	Intermediate Similarity	NPD6234	Discontinued
0.8457	Intermediate Similarity	NPD1465	Phase 2
0.8395	Intermediate Similarity	NPD1934	Approved
0.8333	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.8333	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.8333	Intermediate Similarity	NPD6166	Phase 2
0.8304	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.8282	Intermediate Similarity	NPD37	Approved
0.8242	Intermediate Similarity	NPD4967	Phase 2
0.8242	Intermediate Similarity	NPD4965	Approved
0.8242	Intermediate Similarity	NPD4966	Approved
0.8239	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.8235	Intermediate Similarity	NPD7228	Approved
0.8232	Intermediate Similarity	NPD7819	Suspended
0.8232	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.8182	Intermediate Similarity	NPD3817	Phase 2
0.8155	Intermediate Similarity	NPD7199	Phase 2
0.814	Intermediate Similarity	NPD7074	Phase 3
0.8133	Intermediate Similarity	NPD7768	Phase 2
0.8129	Intermediate Similarity	NPD3818	Discontinued
0.8121	Intermediate Similarity	NPD2801	Approved
0.8086	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.8084	Intermediate Similarity	NPD7075	Discontinued
0.8081	Intermediate Similarity	NPD7054	Approved
0.8068	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.8059	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.805	Intermediate Similarity	NPD3750	Approved
0.8035	Intermediate Similarity	NPD7472	Approved
0.8024	Intermediate Similarity	NPD3882	Suspended
0.7964	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7939	Intermediate Similarity	NPD4380	Phase 2
0.7925	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7904	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7901	Intermediate Similarity	NPD1511	Approved
0.7898	Intermediate Similarity	NPD7808	Phase 3
0.7898	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7885	Intermediate Similarity	NPD230	Phase 1
0.7857	Intermediate Similarity	NPD3027	Phase 3
0.7841	Intermediate Similarity	NPD7685	Pre-registration
0.7841	Intermediate Similarity	NPD7251	Discontinued
0.7841	Intermediate Similarity	NPD6559	Discontinued
0.7836	Intermediate Similarity	NPD6959	Discontinued
0.7805	Intermediate Similarity	NPD1512	Approved
0.7803	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7791	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7784	Intermediate Similarity	NPD7411	Suspended
0.7784	Intermediate Similarity	NPD6797	Phase 2
0.7778	Intermediate Similarity	NPD5494	Approved
0.7778	Intermediate Similarity	NPD6190	Approved
0.7771	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7765	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7753	Intermediate Similarity	NPD8312	Approved
0.7753	Intermediate Similarity	NPD8313	Approved
0.7751	Intermediate Similarity	NPD5402	Approved
0.774	Intermediate Similarity	NPD7240	Approved
0.7738	Intermediate Similarity	NPD6801	Discontinued
0.7736	Intermediate Similarity	NPD3748	Approved
0.7733	Intermediate Similarity	NPD8127	Discontinued
0.7716	Intermediate Similarity	NPD4628	Phase 3
0.7711	Intermediate Similarity	NPD1653	Approved
0.7707	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7707	Intermediate Similarity	NPD1613	Approved
0.7688	Intermediate Similarity	NPD2935	Discontinued
0.7683	Intermediate Similarity	NPD6799	Approved
0.7661	Intermediate Similarity	NPD3749	Approved
0.7654	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7651	Intermediate Similarity	NPD5403	Approved
0.765	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7636	Intermediate Similarity	NPD2533	Approved
0.7636	Intermediate Similarity	NPD2534	Approved
0.7636	Intermediate Similarity	NPD2532	Approved
0.7625	Intermediate Similarity	NPD1510	Phase 2
0.7619	Intermediate Similarity	NPD6599	Discontinued
0.7607	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7607	Intermediate Similarity	NPD7003	Approved
0.7607	Intermediate Similarity	NPD8166	Discontinued
0.7593	Intermediate Similarity	NPD1549	Phase 2
0.7588	Intermediate Similarity	NPD8455	Phase 2
0.7586	Intermediate Similarity	NPD7229	Phase 3
0.758	Intermediate Similarity	NPD3764	Approved
0.758	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7571	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7564	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7531	Intermediate Similarity	NPD7266	Discontinued
0.7531	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7531	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.753	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.753	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.753	Intermediate Similarity	NPD5401	Approved
0.753	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.753	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7527	Intermediate Similarity	NPD8434	Phase 2
0.7526	Intermediate Similarity	NPD7680	Approved
0.7514	Intermediate Similarity	NPD7090	Clinical (unspecified phase)
0.7513	Intermediate Similarity	NPD8151	Discontinued
0.75	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7484	Intermediate Similarity	NPD1240	Approved
0.7469	Intermediate Similarity	NPD2796	Approved
0.7469	Intermediate Similarity	NPD1551	Phase 2
0.7468	Intermediate Similarity	NPD6798	Discontinued
0.7456	Intermediate Similarity	NPD3226	Approved
0.7452	Intermediate Similarity	NPD4908	Phase 1
0.7443	Intermediate Similarity	NPD5242	Approved
0.7443	Intermediate Similarity	NPD3926	Phase 2
0.7442	Intermediate Similarity	NPD5353	Approved
0.7438	Intermediate Similarity	NPD447	Suspended
0.7438	Intermediate Similarity	NPD6355	Discontinued
0.7432	Intermediate Similarity	NPD8150	Discontinued
0.7414	Intermediate Similarity	NPD919	Approved
0.7407	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.7391	Intermediate Similarity	NPD1607	Approved
0.7381	Intermediate Similarity	NPD6273	Approved
0.7375	Intermediate Similarity	NPD4060	Phase 1
0.7375	Intermediate Similarity	NPD943	Approved
0.7362	Intermediate Similarity	NPD5408	Approved
0.7362	Intermediate Similarity	NPD2438	Suspended
0.7362	Intermediate Similarity	NPD5404	Approved
0.7362	Intermediate Similarity	NPD5405	Approved
0.7362	Intermediate Similarity	NPD5406	Approved
0.7358	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7355	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7353	Intermediate Similarity	NPD7458	Discontinued
0.7318	Intermediate Similarity	NPD3751	Discontinued
0.7312	Intermediate Similarity	NPD6233	Phase 2
0.7308	Intermediate Similarity	NPD7549	Discontinued
0.7289	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7278	Intermediate Similarity	NPD9494	Approved
0.7267	Intermediate Similarity	NPD6385	Approved
0.7267	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7267	Intermediate Similarity	NPD6386	Approved
0.7262	Intermediate Similarity	NPD7390	Discontinued
0.7261	Intermediate Similarity	NPD2797	Approved
0.7256	Intermediate Similarity	NPD6099	Approved
0.7256	Intermediate Similarity	NPD6100	Approved
0.7253	Intermediate Similarity	NPD7039	Approved
0.7253	Intermediate Similarity	NPD7038	Approved
0.7241	Intermediate Similarity	NPD4288	Approved
0.7233	Intermediate Similarity	NPD6832	Phase 2
0.7222	Intermediate Similarity	NPD1933	Approved
0.7212	Intermediate Similarity	NPD2346	Discontinued
0.7211	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7197	Intermediate Similarity	NPD1283	Approved
0.7195	Intermediate Similarity	NPD2799	Discontinued
0.7195	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7191	Intermediate Similarity	NPD3787	Discontinued
0.7188	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7186	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.7186	Intermediate Similarity	NPD4110	Phase 3
0.7179	Intermediate Similarity	NPD9269	Phase 2
0.7175	Intermediate Similarity	NPD6746	Phase 2
0.7172	Intermediate Similarity	NPD7783	Phase 2
0.7172	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7165	Intermediate Similarity	NPD7435	Discontinued
0.716	Intermediate Similarity	NPD2979	Phase 3
0.7151	Intermediate Similarity	NPD3455	Phase 2
0.7143	Intermediate Similarity	NPD3268	Approved
0.7135	Intermediate Similarity	NPD1247	Approved
0.7127	Intermediate Similarity	NPD7177	Discontinued
0.7126	Intermediate Similarity	NPD6674	Discontinued
0.7115	Intermediate Similarity	NPD1610	Phase 2
0.7108	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7095	Intermediate Similarity	NPD5711	Approved
0.7095	Intermediate Similarity	NPD5710	Approved
0.7091	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7091	Intermediate Similarity	NPD4308	Phase 3
0.7081	Intermediate Similarity	NPD4625	Phase 3
0.7081	Intermediate Similarity	NPD7095	Approved
0.7076	Intermediate Similarity	NPD1940	Clinical (unspecified phase)
0.707	Intermediate Similarity	NPD1608	Approved
0.7063	Intermediate Similarity	NPD3018	Phase 2
0.7062	Intermediate Similarity	NPD6971	Discontinued
0.7055	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.7055	Intermediate Similarity	NPD3620	Phase 2
0.7044	Intermediate Similarity	NPD1203	Approved
0.7041	Intermediate Similarity	NPD7871	Phase 2
0.7041	Intermediate Similarity	NPD7870	Phase 2
0.7035	Intermediate Similarity	NPD920	Approved
0.7035	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7035	Intermediate Similarity	NPD7874	Approved
0.7026	Intermediate Similarity	NPD6823	Phase 2
0.7024	Intermediate Similarity	NPD1652	Phase 2
0.7012	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7012	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7012	Intermediate Similarity	NPD5124	Phase 1
0.7011	Intermediate Similarity	NPD5953	Discontinued
0.701	Intermediate Similarity	NPD6780	Approved
0.701	Intermediate Similarity	NPD6782	Approved
0.701	Intermediate Similarity	NPD6781	Approved
0.701	Intermediate Similarity	NPD6777	Approved
0.701	Intermediate Similarity	NPD6776	Approved
0.701	Intermediate Similarity	NPD6778	Approved
0.701	Intermediate Similarity	NPD6779	Approved
0.7006	Intermediate Similarity	NPD5763	Approved
0.7006	Intermediate Similarity	NPD1281	Approved
0.7006	Intermediate Similarity	NPD422	Phase 1
0.7006	Intermediate Similarity	NPD5762	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