NPASS Compound

Structure

NPC469512 OpenBabel07101718182D 35 38 0 0 1 0 0 0 0 0999 V2000 2.1847 -4.6650 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4896 -3.5105 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.8668 -1.6483 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0507 -2.5576 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2776 3.7632 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8417 2.9193 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9267 2.6220 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1507 -4.5378 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9666 -0.3011 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.7648 1.2317 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7705 -1.7626 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5727 -0.7883 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5236 -3.6376 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9666 -1.2755 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 4.2776 0.3879 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6143 -1.2755 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2776 2.0755 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9267 -1.2755 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3033 0.3879 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6143 -0.3011 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3033 -1.9644 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.9304 -2.8646 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8161 1.2317 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3033 2.0755 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9267 -0.3011 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7705 0.1861 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2776 -1.9644 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.9644 -2.9918 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.8417 1.2317 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.1505 -2.9305 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.7648 2.9193 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.8161 2.9193 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7705 2.1348 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -1.5765 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 1 8 1 0 0 0 0 2 13 1 0 0 0 0 3 14 1 0 0 0 0 5 31 1 0 0 0 0 6 32 1 0 0 0 0 7 33 1 0 0 0 0 8 13 2 0 0 0 0 9 14 1 0 0 0 0 9 15 1 0 0 0 0 10 15 2 0 0 0 0 10 17 1 0 0 0 0 11 16 2 0 0 0 0 11 18 1 0 0 0 0 12 34 1 0 0 0 0 12 35 1 0 0 0 0 13 22 1 0 0 0 0 14 27 1 6 0 0 0 15 19 1 0 0 0 0 16 20 1 0 0 0 0 16 21 1 0 0 0 0 17 24 2 0 0 0 0 17 31 1 0 0 0 0 18 25 2 0 0 0 0 18 34 1 0 0 0 0 19 20 1 0 0 0 0 19 23 2 0 0 0 0 20 26 2 0 0 0 0 21 22 1 0 0 0 0 21 27 1 1 0 0 0 22 28 2 0 0 0 0 23 24 1 0 0 0 0 23 29 1 0 0 0 0 24 32 1 0 0 0 0 25 26 1 0 0 0 0 25 35 1 0 0 0 0 26 33 1 0 0 0 0 27 4 1 1 0 0 0 27 30 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	484.21
Volume:	490.552
LogP:	3.884
LogD:	3.319
LogS:	-4.864
# Rotatable Bonds:	5
TPSA:	103.68
# H-Bond Aceptor:	8
# H-Bond Donor:	2
# Rings:	4
# Heavy Atoms:	8

MedChem Properties

QED Drug-Likeness Score:	0.603
Synthetic Accessibility Score:	4.272
Fsp3:	0.444
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.784
MDCK Permeability:	2.6004390747402795e-05
Pgp-inhibitor:	0.968
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.006
20% Bioavailability (F20%):	0.012
30% Bioavailability (F30%):	0.059

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.015
Plasma Protein Binding (PPB):	91.29218292236328%
Volume Distribution (VD):	0.755
Pgp-substrate:	7.20914363861084%

ADMET: Metabolism

CYP1A2-inhibitor:	0.188
CYP1A2-substrate:	0.975
CYP2C19-inhibitor:	0.751
CYP2C19-substrate:	0.857
CYP2C9-inhibitor:	0.353
CYP2C9-substrate:	0.858
CYP2D6-inhibitor:	0.404
CYP2D6-substrate:	0.386
CYP3A4-inhibitor:	0.894
CYP3A4-substrate:	0.735

ADMET: Excretion

Clearance (CL):	8.977
Half-life (T1/2):	0.105

ADMET: Toxicity

hERG Blockers:	0.039
Human Hepatotoxicity (H-HT):	0.203
Drug-inuced Liver Injury (DILI):	0.215
AMES Toxicity:	0.016
Rat Oral Acute Toxicity:	0.388
Maximum Recommended Daily Dose:	0.364
Skin Sensitization:	0.165
Carcinogencity:	0.06
Eye Corrosion:	0.003
Eye Irritation:	0.091
Respiratory Toxicity:	0.733

Download Data

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

Natural Product: NPC469512

Natural Product ID:	NPC469512
*Common Name:**	Arisanschinin H
IUPAC Name:	n.a.
Synonyms:	Arisanschinin H
Standard InCHIKey:	KBYDHOPBQPIANF-OQJDONTRSA-N
Standard InCHI:	InChI=1S/C27H32O8/c1-8-13(2)22(28)21-16-11-18-25(35-12-34-18)26(33-7)20(16)19-15(9-14(3)27(21,4)30)10-17(31-5)24(32-6)23(19)29/h8,10-11,14,21,29-30H,9,12H2,1-7H3/b13-8-/t14-,21+,27-/m0/s1
SMILES:	CC=C(C)C(=O)C1C2=CC3=C(C(=C2C4=C(C(=C(C=C4CC(C1(C)O)C)OC)OC)O)OC)OCO3
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1081696
PubChem CID:	46883431
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
NPO8584	Schisandra arisanensis	Species	Schisandraceae	Eukaryota	fruits	n.a.	n.a.	PMID[19673515]
NPO8584	Schisandra arisanensis	Species	Schisandraceae	Eukaryota	fruits	n.a.	n.a.	PMID[20536188]
NPO8584	Schisandra arisanensis	Species	Schisandraceae	Eukaryota	fruits	n.a.	n.a.	PMID[23265871]
NPO8584	Schisandra arisanensis	Species	Schisandraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO8584	Schisandra arisanensis	Species	Schisandraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO8584	Schisandra arisanensis	Species	Schisandraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	NP ID	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
Others	3

Activity Type	# Activity
Cell Line	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT927	Cell Line	PBMC	Homo sapiens	Inhibition	=	12.7	%	PMID[453443]
NPT927	Cell Line	PBMC	Homo sapiens	Inhibition	=	16.4	%	PMID[453443]
NPT927	Cell Line	PBMC	Homo sapiens	Inhibition	=	14.6	%	PMID[453443]

☑ 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 NPC469512 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	396
0.1-0.2	1557
0.2-0.3	3607
0.3-0.4	9081
0.4-0.5	9573
0.5-0.6	3540
0.6-0.7	5249
0.7-0.8	7877
0.8-0.85	1632
0.85-0.9	174
0.9-0.95	8
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9679	High Similarity	NPC469475
0.9679	High Similarity	NPC469518
0.9321	High Similarity	NPC469506
0.9295	High Similarity	NPC469474
0.9202	High Similarity	NPC178737
0.9141	High Similarity	NPC477883
0.9085	High Similarity	NPC471181
0.9068	High Similarity	NPC475865
0.9051	High Similarity	NPC477380
0.9038	High Similarity	NPC272566
0.9038	High Similarity	NPC220577
0.903	High Similarity	NPC477881
0.8994	High Similarity	NPC477885
0.8994	High Similarity	NPC475592
0.8987	High Similarity	NPC238834
0.8987	High Similarity	NPC476065
0.8963	High Similarity	NPC88557
0.8903	High Similarity	NPC304821
0.8902	High Similarity	NPC471180
0.8902	High Similarity	NPC311912
0.8896	High Similarity	NPC475738
0.8869	High Similarity	NPC477882
0.8869	High Similarity	NPC477880
0.8861	High Similarity	NPC53669
0.8861	High Similarity	NPC126405
0.8861	High Similarity	NPC16791
0.8861	High Similarity	NPC77237
0.8861	High Similarity	NPC217708
0.8861	High Similarity	NPC297271
0.8861	High Similarity	NPC474606
0.8861	High Similarity	NPC308739
0.8854	High Similarity	NPC234152
0.8841	High Similarity	NPC320471
0.8841	High Similarity	NPC83049
0.8841	High Similarity	NPC118162
0.882	High Similarity	NPC325122
0.8797	High Similarity	NPC471154
0.8774	High Similarity	NPC87295
0.8773	High Similarity	NPC61141
0.8773	High Similarity	NPC76687
0.8765	High Similarity	NPC474770
0.8758	High Similarity	NPC133934
0.8758	High Similarity	NPC474990
0.8758	High Similarity	NPC184641
0.8758	High Similarity	NPC184684
0.8742	High Similarity	NPC474514
0.8742	High Similarity	NPC24562
0.8734	High Similarity	NPC224472
0.8734	High Similarity	NPC475756
0.8712	High Similarity	NPC295009
0.8712	High Similarity	NPC260640
0.8704	High Similarity	NPC230531
0.8704	High Similarity	NPC215400
0.8688	High Similarity	NPC198461
0.8688	High Similarity	NPC287504
0.8683	High Similarity	NPC212748
0.8675	High Similarity	NPC79322
0.8671	High Similarity	NPC470916
0.8667	High Similarity	NPC477884
0.8667	High Similarity	NPC39306
0.8659	High Similarity	NPC42797
0.865	High Similarity	NPC285973
0.865	High Similarity	NPC225624
0.8645	High Similarity	NPC73467
0.8645	High Similarity	NPC121661
0.8642	High Similarity	NPC167595
0.8642	High Similarity	NPC472963
0.8631	High Similarity	NPC235575
0.8631	High Similarity	NPC261254
0.8625	High Similarity	NPC35544
0.8625	High Similarity	NPC104728
0.8608	High Similarity	NPC474347
0.8608	High Similarity	NPC474393
0.8606	High Similarity	NPC291977
0.8606	High Similarity	NPC133065
0.8599	High Similarity	NPC88345
0.8598	High Similarity	NPC94155
0.859	High Similarity	NPC189239
0.859	High Similarity	NPC197352
0.859	High Similarity	NPC110763
0.859	High Similarity	NPC166506
0.8589	High Similarity	NPC215375
0.8589	High Similarity	NPC62518
0.858	High Similarity	NPC472907
0.858	High Similarity	NPC473323
0.8571	High Similarity	NPC312763
0.8571	High Similarity	NPC348849
0.8571	High Similarity	NPC25127
0.8571	High Similarity	NPC178195
0.8562	High Similarity	NPC104353
0.8562	High Similarity	NPC53722
0.8562	High Similarity	NPC201404
0.8562	High Similarity	NPC477699
0.8562	High Similarity	NPC290714
0.8553	High Similarity	NPC177830
0.8553	High Similarity	NPC316989
0.8547	High Similarity	NPC170203
0.8545	High Similarity	NPC472964
0.8545	High Similarity	NPC469575
0.8545	High Similarity	NPC473445
0.8544	High Similarity	NPC198129
0.8544	High Similarity	NPC477375
0.8544	High Similarity	NPC252281
0.8544	High Similarity	NPC327352
0.8535	High Similarity	NPC296575
0.8535	High Similarity	NPC252286
0.8535	High Similarity	NPC154971
0.8535	High Similarity	NPC472560
0.8526	High Similarity	NPC16353
0.8519	High Similarity	NPC79998
0.8519	High Similarity	NPC38898
0.85	High Similarity	NPC85131
0.85	High Similarity	NPC472279
0.85	High Similarity	NPC32079
0.85	High Similarity	NPC477700
0.8494	Intermediate Similarity	NPC475985
0.8491	Intermediate Similarity	NPC477374
0.8491	Intermediate Similarity	NPC322426
0.8491	Intermediate Similarity	NPC474903
0.8491	Intermediate Similarity	NPC477376
0.8485	Intermediate Similarity	NPC162668
0.8485	Intermediate Similarity	NPC319749
0.8481	Intermediate Similarity	NPC295297
0.8481	Intermediate Similarity	NPC138978
0.848	Intermediate Similarity	NPC257714
0.8476	Intermediate Similarity	NPC476242
0.8471	Intermediate Similarity	NPC207732
0.8466	Intermediate Similarity	NPC54928
0.8466	Intermediate Similarity	NPC29727
0.8466	Intermediate Similarity	NPC150227
0.8462	Intermediate Similarity	NPC324962
0.8457	Intermediate Similarity	NPC136757
0.8457	Intermediate Similarity	NPC57211
0.8457	Intermediate Similarity	NPC250557
0.8457	Intermediate Similarity	NPC473425
0.8457	Intermediate Similarity	NPC472905
0.8452	Intermediate Similarity	NPC229729
0.8452	Intermediate Similarity	NPC126204
0.8452	Intermediate Similarity	NPC76482
0.8447	Intermediate Similarity	NPC78505
0.8447	Intermediate Similarity	NPC151425
0.8443	Intermediate Similarity	NPC165720
0.8438	Intermediate Similarity	NPC102003
0.8438	Intermediate Similarity	NPC92722
0.8434	Intermediate Similarity	NPC280778
0.8434	Intermediate Similarity	NPC312056
0.8434	Intermediate Similarity	NPC300537
0.8434	Intermediate Similarity	NPC127782
0.8434	Intermediate Similarity	NPC84515
0.8431	Intermediate Similarity	NPC471182
0.843	Intermediate Similarity	NPC241196
0.8428	Intermediate Similarity	NPC316676
0.8428	Intermediate Similarity	NPC325720
0.8424	Intermediate Similarity	NPC269906
0.8424	Intermediate Similarity	NPC472902
0.8424	Intermediate Similarity	NPC474960
0.8418	Intermediate Similarity	NPC224687
0.8418	Intermediate Similarity	NPC321696
0.8418	Intermediate Similarity	NPC321958
0.8418	Intermediate Similarity	NPC157133
0.8415	Intermediate Similarity	NPC199463
0.8415	Intermediate Similarity	NPC190020
0.8415	Intermediate Similarity	NPC299520
0.8415	Intermediate Similarity	NPC77679
0.8415	Intermediate Similarity	NPC37543
0.8415	Intermediate Similarity	NPC163527
0.8415	Intermediate Similarity	NPC115281
0.8415	Intermediate Similarity	NPC84935
0.8415	Intermediate Similarity	NPC181168
0.8415	Intermediate Similarity	NPC241904
0.8415	Intermediate Similarity	NPC300727
0.8415	Intermediate Similarity	NPC129684
0.8412	Intermediate Similarity	NPC475825
0.8412	Intermediate Similarity	NPC260263
0.8412	Intermediate Similarity	NPC223375
0.8408	Intermediate Similarity	NPC46880
0.8408	Intermediate Similarity	NPC254659
0.8408	Intermediate Similarity	NPC471417
0.8408	Intermediate Similarity	NPC119663
0.8405	Intermediate Similarity	NPC18954
0.8405	Intermediate Similarity	NPC199926
0.8402	Intermediate Similarity	NPC476771
0.8402	Intermediate Similarity	NPC117911
0.8402	Intermediate Similarity	NPC229687
0.8402	Intermediate Similarity	NPC473202
0.8402	Intermediate Similarity	NPC211309
0.8397	Intermediate Similarity	NPC36531
0.8397	Intermediate Similarity	NPC229172
0.8397	Intermediate Similarity	NPC110419
0.8397	Intermediate Similarity	NPC103637
0.8397	Intermediate Similarity	NPC230538
0.8395	Intermediate Similarity	NPC474993
0.8395	Intermediate Similarity	NPC52623
0.8395	Intermediate Similarity	NPC149735
0.8393	Intermediate Similarity	NPC170245
0.8393	Intermediate Similarity	NPC235610
0.8393	Intermediate Similarity	NPC113093
0.8393	Intermediate Similarity	NPC5778
0.8393	Intermediate Similarity	NPC254306
0.8393	Intermediate Similarity	NPC236934

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 NPC469512 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	349
0.1-0.2	930
0.2-0.3	1851
0.3-0.4	2713
0.4-0.5	1796
0.5-0.6	958
0.6-0.7	409
0.7-0.8	125
0.8-0.85	19
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8563	High Similarity	NPD3818	Discontinued
0.8393	Intermediate Similarity	NPD7473	Discontinued
0.8364	Intermediate Similarity	NPD6234	Discontinued
0.8353	Intermediate Similarity	NPD7074	Phase 3
0.8294	Intermediate Similarity	NPD7054	Approved
0.8282	Intermediate Similarity	NPD37	Approved
0.8246	Intermediate Similarity	NPD7472	Approved
0.8242	Intermediate Similarity	NPD3882	Suspended
0.8214	Intermediate Similarity	NPD6232	Discontinued
0.8199	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.8171	Intermediate Similarity	NPD1934	Approved
0.8155	Intermediate Similarity	NPD7199	Phase 2
0.8133	Intermediate Similarity	NPD4967	Phase 2
0.8133	Intermediate Similarity	NPD4965	Approved
0.8133	Intermediate Similarity	NPD4966	Approved
0.8129	Intermediate Similarity	NPD7228	Approved
0.8121	Intermediate Similarity	NPD2801	Approved
0.8068	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.8059	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.8046	Intermediate Similarity	NPD7251	Discontinued
0.8012	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.8012	Intermediate Similarity	NPD1465	Phase 2
0.8	Intermediate Similarity	NPD7808	Phase 3
0.7989	Intermediate Similarity	NPD6797	Phase 2
0.7976	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7917	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7907	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7907	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7907	Intermediate Similarity	NPD6166	Phase 2
0.7901	Intermediate Similarity	NPD1511	Approved
0.7901	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7898	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7857	Intermediate Similarity	NPD3817	Phase 2
0.7841	Intermediate Similarity	NPD6559	Discontinued
0.7812	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7805	Intermediate Similarity	NPD1512	Approved
0.7798	Intermediate Similarity	NPD7819	Suspended
0.7778	Intermediate Similarity	NPD5494	Approved
0.7735	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7725	Intermediate Similarity	NPD4380	Phase 2
0.7707	Intermediate Similarity	NPD1240	Approved
0.767	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.767	Intermediate Similarity	NPD5844	Phase 1
0.7661	Intermediate Similarity	NPD7075	Discontinued
0.7644	Intermediate Similarity	NPD3926	Phase 2
0.764	Intermediate Similarity	NPD7685	Pre-registration
0.764	Intermediate Similarity	NPD7240	Approved
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
0.7614	Intermediate Similarity	NPD3751	Discontinued
0.761	Intermediate Similarity	NPD1607	Approved
0.7595	Intermediate Similarity	NPD943	Approved
0.7558	Intermediate Similarity	NPD3749	Approved
0.7554	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.753	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7529	Intermediate Similarity	NPD6959	Discontinued
0.7516	Intermediate Similarity	NPD3027	Phase 3
0.7514	Intermediate Similarity	NPD7090	Clinical (unspecified phase)
0.7486	Intermediate Similarity	NPD3787	Discontinued
0.7486	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7485	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.747	Intermediate Similarity	NPD6799	Approved
0.7469	Intermediate Similarity	NPD6100	Approved
0.7469	Intermediate Similarity	NPD6099	Approved
0.7442	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7438	Intermediate Similarity	NPD230	Phase 1
0.7425	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7414	Intermediate Similarity	NPD919	Approved
0.7412	Intermediate Similarity	NPD6599	Discontinued
0.7407	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7396	Intermediate Similarity	NPD1653	Approved
0.7394	Intermediate Similarity	NPD3750	Approved
0.7378	Intermediate Similarity	NPD1549	Phase 2
0.7362	Intermediate Similarity	NPD2935	Discontinued
0.7355	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7337	Intermediate Similarity	NPD8434	Phase 2
0.7333	Intermediate Similarity	NPD8151	Discontinued
0.733	Intermediate Similarity	NPD1247	Approved
0.7326	Intermediate Similarity	NPD6801	Discontinued
0.7317	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7317	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7316	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.731	Intermediate Similarity	NPD7028	Phase 2
0.7289	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7289	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7284	Intermediate Similarity	NPD6651	Approved
0.7278	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7268	Intermediate Similarity	NPD8312	Approved
0.7268	Intermediate Similarity	NPD8313	Approved
0.7267	Intermediate Similarity	NPD7411	Suspended
0.7262	Intermediate Similarity	NPD7390	Discontinued
0.7256	Intermediate Similarity	NPD2796	Approved
0.7251	Intermediate Similarity	NPD7458	Discontinued
0.725	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7246	Intermediate Similarity	NPD6190	Approved
0.7233	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7229	Intermediate Similarity	NPD2800	Approved
0.7226	Intermediate Similarity	NPD3705	Approved
0.7212	Intermediate Similarity	NPD7266	Discontinued
0.7207	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.72	Intermediate Similarity	NPD7768	Phase 2
0.7195	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7191	Intermediate Similarity	NPD7229	Phase 3
0.7188	Intermediate Similarity	NPD6780	Approved
0.7188	Intermediate Similarity	NPD6778	Approved
0.7188	Intermediate Similarity	NPD6777	Approved
0.7188	Intermediate Similarity	NPD6781	Approved
0.7188	Intermediate Similarity	NPD6779	Approved
0.7188	Intermediate Similarity	NPD6782	Approved
0.7188	Intermediate Similarity	NPD6776	Approved
0.7165	Intermediate Similarity	NPD7680	Approved
0.7165	Intermediate Similarity	NPD7435	Discontinued
0.716	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.716	Intermediate Similarity	NPD1613	Approved
0.7143	Intermediate Similarity	NPD5402	Approved
0.7126	Intermediate Similarity	NPD1243	Approved
0.7118	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7108	Intermediate Similarity	NPD2344	Approved
0.7107	Intermediate Similarity	NPD2798	Approved
0.7098	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7095	Intermediate Similarity	NPD5711	Approved
0.7095	Intermediate Similarity	NPD5710	Approved
0.7091	Intermediate Similarity	NPD3748	Approved
0.7083	Intermediate Similarity	NPD4628	Phase 3
0.7077	Intermediate Similarity	NPD7697	Approved
0.7077	Intermediate Similarity	NPD7698	Approved
0.7077	Intermediate Similarity	NPD7696	Phase 3
0.7063	Intermediate Similarity	NPD9494	Approved
0.7052	Intermediate Similarity	NPD3226	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	NPD5403	Approved
0.7026	Intermediate Similarity	NPD6823	Phase 2
0.7024	Intermediate Similarity	NPD6674	Discontinued
0.702	Intermediate Similarity	NPD7701	Phase 2
0.7012	Intermediate Similarity	NPD1933	Approved
0.7012	Intermediate Similarity	NPD447	Suspended
0.7	Intermediate Similarity	NPD7801	Approved
0.6989	Remote Similarity	NPD8455	Phase 2
0.698	Remote Similarity	NPD7930	Approved
0.6968	Remote Similarity	NPD8150	Discontinued
0.6962	Remote Similarity	NPD9269	Phase 2
0.6961	Remote Similarity	NPD5242	Approved
0.6959	Remote Similarity	NPD4357	Discontinued
0.6957	Remote Similarity	NPD3018	Phase 2
0.695	Remote Similarity	NPD7874	Approved
0.695	Remote Similarity	NPD7875	Clinical (unspecified phase)
0.6949	Remote Similarity	NPD5353	Approved
0.6946	Remote Similarity	NPD1551	Phase 2
0.6944	Remote Similarity	NPD8127	Discontinued
0.6941	Remote Similarity	NPD2309	Approved
0.6933	Remote Similarity	NPD3764	Approved
0.6931	Remote Similarity	NPD6841	Approved
0.6931	Remote Similarity	NPD6843	Phase 3
0.6931	Remote Similarity	NPD6842	Approved
0.6927	Remote Similarity	NPD6535	Approved
0.6927	Remote Similarity	NPD6534	Approved
0.6923	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6919	Remote Similarity	NPD5401	Approved
0.6919	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6919	Remote Similarity	NPD642	Clinical (unspecified phase)
0.6915	Remote Similarity	NPD7783	Phase 2
0.6915	Remote Similarity	NPD7782	Clinical (unspecified phase)
0.6909	Remote Similarity	NPD6355	Discontinued
0.6907	Remote Similarity	NPD7699	Phase 2
0.6907	Remote Similarity	NPD7700	Phase 2
0.6903	Remote Similarity	NPD5536	Phase 2
0.6901	Remote Similarity	NPD643	Clinical (unspecified phase)
0.6886	Remote Similarity	NPD2799	Discontinued
0.6884	Remote Similarity	NPD7584	Approved
0.6882	Remote Similarity	NPD8166	Discontinued
0.6875	Remote Similarity	NPD1283	Approved
0.6872	Remote Similarity	NPD7975	Clinical (unspecified phase)
0.6871	Remote Similarity	NPD4625	Phase 3
0.6869	Remote Similarity	NPD8320	Phase 1
0.6869	Remote Similarity	NPD8319	Approved
0.6855	Remote Similarity	NPD1608	Approved
0.6853	Remote Similarity	NPD5005	Approved
0.6853	Remote Similarity	NPD5006	Approved
0.6848	Remote Similarity	NPD4060	Phase 1
0.6845	Remote Similarity	NPD4419	Clinical (unspecified phase)
0.6831	Remote Similarity	NPD2403	Approved
0.6829	Remote Similarity	NPD3268	Approved
0.6828	Remote Similarity	NPD5953	Discontinued
0.6824	Remote Similarity	NPD2654	Approved
0.6823	Remote Similarity	NPD7296	Approved
0.6813	Remote Similarity	NPD2982	Phase 2
0.6813	Remote Similarity	NPD2983	Phase 2
0.6811	Remote Similarity	NPD7286	Phase 2
0.681	Remote Similarity	NPD4908	Phase 1
0.6805	Remote Similarity	NPD2346	Discontinued
0.6786	Remote Similarity	NPD7033	Discontinued
0.6784	Remote Similarity	NPD7003	Approved
0.678	Remote Similarity	NPD5089	Approved
0.678	Remote Similarity	NPD5090	Approved
0.678	Remote Similarity	NPD6386	Approved
0.678	Remote Similarity	NPD6385	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