NPASS Compound

Structure

NPC93869 OpenBabel07101719512D 31 32 0 0 1 0 0 0 0 0999 V2000 0.8660 4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2709 -1.2321 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6831 1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4752 -1.2872 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.7709 -0.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 1.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.2709 0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8660 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8660 -0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.6831 -0.3090 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.2183 -1.9563 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.7709 -0.3660 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4263 -0.9781 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 3.0000 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 -4.2709 0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 12 1 0 0 0 0 2 12 1 0 0 0 0 3 13 1 0 0 0 0 4 13 1 0 0 0 0 5 14 1 0 0 0 0 6 12 1 0 0 0 0 6 18 1 0 0 0 0 7 13 1 0 0 0 0 7 19 1 0 0 0 0 8 17 1 0 0 0 0 9 15 1 0 0 0 0 9 28 1 0 0 0 0 10 15 2 0 0 0 0 10 29 1 0 0 0 0 11 22 1 0 0 0 0 11 23 1 0 0 0 0 14 24 2 0 0 0 0 14 30 1 0 0 0 0 15 16 1 0 0 0 0 16 8 1 6 0 0 0 16 20 1 0 0 0 0 17 22 1 1 0 0 0 17 30 1 0 0 0 0 18 25 2 0 0 0 0 18 28 1 0 0 0 0 19 26 2 0 0 0 0 19 31 1 0 0 0 0 20 21 1 0 0 0 0 20 22 1 6 0 0 0 21 29 1 0 0 0 0 21 31 1 1 0 0 0 22 27 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	442.22
Volume:	440.521
LogP:	2.685
LogD:	1.71
LogS:	-3.606
# Rotatable Bonds:	12
TPSA:	128.59
# H-Bond Aceptor:	9
# H-Bond Donor:	2
# Rings:	2
# Heavy Atoms:	9

MedChem Properties

QED Drug-Likeness Score:	0.405
Synthetic Accessibility Score:	4.514
Fsp3:	0.773
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.684
MDCK Permeability:	7.147067663026974e-05
Pgp-inhibitor:	0.435
Pgp-substrate:	0.002
Human Intestinal Absorption (HIA):	0.005
20% Bioavailability (F20%):	0.006
30% Bioavailability (F30%):	0.991

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.912
Plasma Protein Binding (PPB):	57.601375579833984%
Volume Distribution (VD):	0.665
Pgp-substrate:	33.25212097167969%

ADMET: Metabolism

CYP1A2-inhibitor:	0.054
CYP1A2-substrate:	0.022
CYP2C19-inhibitor:	0.013
CYP2C19-substrate:	0.118
CYP2C9-inhibitor:	0.035
CYP2C9-substrate:	0.055
CYP2D6-inhibitor:	0.024
CYP2D6-substrate:	0.032
CYP3A4-inhibitor:	0.347
CYP3A4-substrate:	0.242

ADMET: Excretion

Clearance (CL):	5.5
Half-life (T1/2):	0.859

ADMET: Toxicity

hERG Blockers:	0.018
Human Hepatotoxicity (H-HT):	0.623
Drug-inuced Liver Injury (DILI):	0.903
AMES Toxicity:	0.985
Rat Oral Acute Toxicity:	0.147
Maximum Recommended Daily Dose:	0.824
Skin Sensitization:	0.887
Carcinogencity:	0.958
Eye Corrosion:	0.079
Eye Irritation:	0.184
Respiratory Toxicity:	0.945

Download Data

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

Natural Product: NPC93869

Natural Product ID:	NPC93869
*Common Name:**	Jatamanvaltrate H
IUPAC Name:	[(1S,4aS,6S,7R,7aS)-6-acetyloxy-7-hydroxy-7-(hydroxymethyl)-1-(3-methylbutanoyloxy)-4a,5,6,7a-tetrahydro-1H-cyclopenta[c]pyran-4-yl]methyl 3-methylbutanoate
Synonyms:	jatamanvaltrate H
Standard InCHIKey:	GGDYOYOEMNQXNC-PNBTUHDLSA-N
Standard InCHI:	InChI=1S/C22H34O9/c1-12(2)6-18(25)28-9-15-10-29-21(31-19(26)7-13(3)4)20-16(15)8-17(30-14(5)24)22(20,27)11-23/h10,12-13,16-17,20-21,23,27H,6-9,11H2,1-5H3/t16-,17+,20-,21+,22-/m1/s1
SMILES:	CC(C)CC(=O)OCC1=CO[C@H]([C@H]2[C@@H]1C[C@@H]([C@@]2(CO)O)OC(=O)C)OC(=O)CC(C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL559515
PubChem CID:	42640470
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001549] Monoterpenoids [CHEMONTID:0001565] Iridoids and derivatives

*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
NPO29016	Valeriana jatamansi	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19245261]
NPO29016	Valeriana jatamansi	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20151678]
NPO29016	Valeriana jatamansi	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20853876]
NPO29016	Valeriana jatamansi	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO29016	Valeriana jatamansi	Species	Caprifoliaceae	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
IC50	4

Activity Type	# Activity
Cell Line	3
NON-MOLECULAR	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT81	Cell Line	A549	Homo sapiens	IC50	>	10000.0	nM	PMID[466536]
NPT180	Cell Line	HCT-8	Homo sapiens	IC50	>	10000.0	nM	PMID[466536]
NPT181	Cell Line	Bel-7402	Homo sapiens	IC50	>	10000.0	nM	PMID[466536]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	5200.0	nM	PMID[466536]

☑ 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 NPC93869 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	223
0.1-0.2	1825
0.2-0.3	6048
0.3-0.4	14288
0.4-0.5	9490
0.5-0.6	7743
0.6-0.7	2819
0.7-0.8	217
0.8-0.85	14
0.85-0.9	12
0.9-0.95	11
0.95-1	7

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC6765
0.9886	High Similarity	NPC274588
0.9667	High Similarity	NPC170527
0.9462	High Similarity	NPC216911
0.9355	High Similarity	NPC476211
0.9355	High Similarity	NPC476320
0.9348	High Similarity	NPC86843
0.9263	High Similarity	NPC329834
0.9255	High Similarity	NPC476230
0.9255	High Similarity	NPC27474
0.9239	High Similarity	NPC284063
0.9222	High Similarity	NPC235051
0.9222	High Similarity	NPC66504
0.9062	High Similarity	NPC329704
0.9053	High Similarity	NPC476228
0.8866	High Similarity	NPC37240
0.8763	High Similarity	NPC4899
0.8763	High Similarity	NPC35185
0.8763	High Similarity	NPC474730
0.8763	High Similarity	NPC177013
0.8687	High Similarity	NPC170432
0.8673	High Similarity	NPC475928
0.8614	High Similarity	NPC208307
0.86	High Similarity	NPC80338
0.86	High Similarity	NPC148270
0.86	High Similarity	NPC197813
0.8557	High Similarity	NPC244878
0.8529	High Similarity	NPC193741
0.8515	High Similarity	NPC110701
0.8469	Intermediate Similarity	NPC20673
0.8469	Intermediate Similarity	NPC287539
0.8469	Intermediate Similarity	NPC3488
0.8454	Intermediate Similarity	NPC151093
0.8384	Intermediate Similarity	NPC106668
0.8365	Intermediate Similarity	NPC475851
0.8365	Intermediate Similarity	NPC475924
0.8317	Intermediate Similarity	NPC127235
0.83	Intermediate Similarity	NPC27687
0.8283	Intermediate Similarity	NPC98859
0.8283	Intermediate Similarity	NPC219038
0.8283	Intermediate Similarity	NPC4637
0.8211	Intermediate Similarity	NPC274274
0.8211	Intermediate Similarity	NPC294643
0.8211	Intermediate Similarity	NPC473150
0.82	Intermediate Similarity	NPC471599
0.8191	Intermediate Similarity	NPC50464
0.8191	Intermediate Similarity	NPC93190
0.8163	Intermediate Similarity	NPC304445
0.8163	Intermediate Similarity	NPC261372
0.8163	Intermediate Similarity	NPC236580
0.8163	Intermediate Similarity	NPC58267
0.8163	Intermediate Similarity	NPC263674
0.8125	Intermediate Similarity	NPC470187
0.802	Intermediate Similarity	NPC304163
0.7941	Intermediate Similarity	NPC473148
0.7921	Intermediate Similarity	NPC67296
0.79	Intermediate Similarity	NPC249171
0.79	Intermediate Similarity	NPC49833
0.7879	Intermediate Similarity	NPC161293
0.7879	Intermediate Similarity	NPC474297
0.7857	Intermediate Similarity	NPC63897
0.7812	Intermediate Similarity	NPC22918
0.78	Intermediate Similarity	NPC472290
0.7778	Intermediate Similarity	NPC241407
0.7778	Intermediate Similarity	NPC291709
0.7732	Intermediate Similarity	NPC246173
0.7723	Intermediate Similarity	NPC469918
0.7723	Intermediate Similarity	NPC96399
0.7723	Intermediate Similarity	NPC469919
0.7723	Intermediate Similarity	NPC124181
0.7723	Intermediate Similarity	NPC37866
0.7723	Intermediate Similarity	NPC223700
0.7723	Intermediate Similarity	NPC117066
0.7723	Intermediate Similarity	NPC90819
0.7708	Intermediate Similarity	NPC148534
0.7684	Intermediate Similarity	NPC149018
0.7684	Intermediate Similarity	NPC171484
0.767	Intermediate Similarity	NPC200672
0.767	Intermediate Similarity	NPC214714
0.767	Intermediate Similarity	NPC80144
0.766	Intermediate Similarity	NPC98276
0.766	Intermediate Similarity	NPC259296
0.7653	Intermediate Similarity	NPC276298
0.7647	Intermediate Similarity	NPC473146
0.7647	Intermediate Similarity	NPC130792
0.7624	Intermediate Similarity	NPC153559
0.7624	Intermediate Similarity	NPC470684
0.7624	Intermediate Similarity	NPC474182
0.7624	Intermediate Similarity	NPC470683
0.7619	Intermediate Similarity	NPC470980
0.7604	Intermediate Similarity	NPC31349
0.7604	Intermediate Similarity	NPC258501
0.76	Intermediate Similarity	NPC167893
0.76	Intermediate Similarity	NPC472873
0.7589	Intermediate Similarity	NPC219656
0.7576	Intermediate Similarity	NPC474835
0.7576	Intermediate Similarity	NPC320089
0.7573	Intermediate Similarity	NPC26557
0.7551	Intermediate Similarity	NPC270908
0.7551	Intermediate Similarity	NPC470573
0.7551	Intermediate Similarity	NPC117596
0.7551	Intermediate Similarity	NPC216826
0.7551	Intermediate Similarity	NPC65665
0.7551	Intermediate Similarity	NPC231710
0.7551	Intermediate Similarity	NPC120021
0.7549	Intermediate Similarity	NPC473307
0.7549	Intermediate Similarity	NPC472015
0.7545	Intermediate Similarity	NPC106446
0.7525	Intermediate Similarity	NPC54731
0.7524	Intermediate Similarity	NPC86095
0.75	Intermediate Similarity	NPC475956
0.75	Intermediate Similarity	NPC94919
0.75	Intermediate Similarity	NPC252242
0.75	Intermediate Similarity	NPC470657
0.75	Intermediate Similarity	NPC222062
0.75	Intermediate Similarity	NPC106760
0.7476	Intermediate Similarity	NPC22149
0.7476	Intermediate Similarity	NPC306344
0.7476	Intermediate Similarity	NPC255677
0.7475	Intermediate Similarity	NPC122057
0.7475	Intermediate Similarity	NPC472126
0.7475	Intermediate Similarity	NPC472124
0.7475	Intermediate Similarity	NPC472125
0.7456	Intermediate Similarity	NPC233500
0.7453	Intermediate Similarity	NPC41681
0.7453	Intermediate Similarity	NPC475290
0.7453	Intermediate Similarity	NPC85670
0.7451	Intermediate Similarity	NPC471150
0.7429	Intermediate Similarity	NPC234304
0.7429	Intermediate Similarity	NPC118761
0.7429	Intermediate Similarity	NPC232515
0.7429	Intermediate Similarity	NPC284929
0.7429	Intermediate Similarity	NPC474783
0.7429	Intermediate Similarity	NPC267869
0.7429	Intermediate Similarity	NPC260809
0.7429	Intermediate Similarity	NPC197541
0.7407	Intermediate Similarity	NPC473570
0.7404	Intermediate Similarity	NPC28304
0.7404	Intermediate Similarity	NPC298255
0.74	Intermediate Similarity	NPC472195
0.74	Intermediate Similarity	NPC472196
0.74	Intermediate Similarity	NPC61201
0.74	Intermediate Similarity	NPC238090
0.7396	Intermediate Similarity	NPC477747
0.7396	Intermediate Similarity	NPC477746
0.7391	Intermediate Similarity	NPC196130
0.7379	Intermediate Similarity	NPC79449
0.7379	Intermediate Similarity	NPC474957
0.7374	Intermediate Similarity	NPC202886
0.7374	Intermediate Similarity	NPC307699
0.7368	Intermediate Similarity	NPC474266
0.7368	Intermediate Similarity	NPC239308
0.7363	Intermediate Similarity	NPC279575
0.7358	Intermediate Similarity	NPC474550
0.7358	Intermediate Similarity	NPC473577
0.7358	Intermediate Similarity	NPC475585
0.7347	Intermediate Similarity	NPC233997
0.7345	Intermediate Similarity	NPC13710
0.7339	Intermediate Similarity	NPC27551
0.7339	Intermediate Similarity	NPC114961
0.7333	Intermediate Similarity	NPC470972
0.7333	Intermediate Similarity	NPC310804
0.7333	Intermediate Similarity	NPC261117
0.7333	Intermediate Similarity	NPC475986
0.7333	Intermediate Similarity	NPC13171
0.7333	Intermediate Similarity	NPC195510
0.7328	Intermediate Similarity	NPC219804
0.7327	Intermediate Similarity	NPC159698
0.7327	Intermediate Similarity	NPC256368
0.7327	Intermediate Similarity	NPC472198
0.7321	Intermediate Similarity	NPC277583
0.7321	Intermediate Similarity	NPC5311
0.7321	Intermediate Similarity	NPC199428
0.7321	Intermediate Similarity	NPC193382
0.7321	Intermediate Similarity	NPC99620
0.7321	Intermediate Similarity	NPC310341
0.732	Intermediate Similarity	NPC471480
0.7315	Intermediate Similarity	NPC224414
0.7308	Intermediate Similarity	NPC471381
0.7308	Intermediate Similarity	NPC186861
0.73	Intermediate Similarity	NPC472199
0.73	Intermediate Similarity	NPC472197
0.73	Intermediate Similarity	NPC477749
0.7297	Intermediate Similarity	NPC102619
0.7297	Intermediate Similarity	NPC287075
0.729	Intermediate Similarity	NPC239961
0.7282	Intermediate Similarity	NPC91197
0.7282	Intermediate Similarity	NPC347923
0.7282	Intermediate Similarity	NPC239547
0.7282	Intermediate Similarity	NPC155319
0.7282	Intermediate Similarity	NPC309503
0.7282	Intermediate Similarity	NPC274793
0.7282	Intermediate Similarity	NPC96597
0.7282	Intermediate Similarity	NPC476057
0.7282	Intermediate Similarity	NPC125551
0.7273	Intermediate Similarity	NPC215556
0.7273	Intermediate Similarity	NPC477748
0.7263	Intermediate Similarity	NPC475849
0.7263	Intermediate Similarity	NPC103171
0.7257	Intermediate Similarity	NPC34390

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 NPC93869 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	249
0.1-0.2	2616
0.2-0.3	3726
0.3-0.4	1767
0.4-0.5	471
0.5-0.6	277
0.6-0.7	44
0.7-0.8	0
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.7456	Intermediate Similarity	NPD7503	Approved
0.7455	Intermediate Similarity	NPD8133	Approved
0.7193	Intermediate Similarity	NPD7327	Approved
0.7193	Intermediate Similarity	NPD7328	Approved
0.7156	Intermediate Similarity	NPD6686	Approved
0.713	Intermediate Similarity	NPD7516	Approved
0.7069	Intermediate Similarity	NPD8294	Approved
0.7069	Intermediate Similarity	NPD8377	Approved
0.7059	Intermediate Similarity	NPD7507	Approved
0.7009	Intermediate Similarity	NPD8296	Approved
0.7009	Intermediate Similarity	NPD8335	Approved
0.7009	Intermediate Similarity	NPD8380	Approved
0.7009	Intermediate Similarity	NPD8378	Approved
0.7009	Intermediate Similarity	NPD8379	Approved
0.7009	Intermediate Similarity	NPD8033	Approved
0.6909	Remote Similarity	NPD6412	Phase 2
0.6903	Remote Similarity	NPD6053	Discontinued
0.69	Remote Similarity	NPD4251	Approved
0.69	Remote Similarity	NPD4250	Approved
0.6885	Remote Similarity	NPD7319	Approved
0.6869	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6863	Remote Similarity	NPD6698	Approved
0.6863	Remote Similarity	NPD46	Approved
0.6814	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.68	Remote Similarity	NPD4249	Approved
0.6757	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6729	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6699	Remote Similarity	NPD7838	Discovery
0.6583	Remote Similarity	NPD8513	Phase 3
0.6579	Remote Similarity	NPD6371	Approved
0.6531	Remote Similarity	NPD4822	Approved
0.6531	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6531	Remote Similarity	NPD4821	Approved
0.6531	Remote Similarity	NPD4820	Approved
0.6531	Remote Similarity	NPD4819	Approved
0.6452	Remote Similarity	NPD8293	Discontinued
0.6446	Remote Similarity	NPD8515	Approved
0.6446	Remote Similarity	NPD8516	Approved
0.6446	Remote Similarity	NPD8517	Approved
0.6429	Remote Similarity	NPD4056	Clinical (unspecified phase)
0.6429	Remote Similarity	NPD4057	Clinical (unspecified phase)
0.6422	Remote Similarity	NPD7638	Approved
0.64	Remote Similarity	NPD6435	Approved
0.64	Remote Similarity	NPD7736	Approved
0.6393	Remote Similarity	NPD6370	Approved
0.6364	Remote Similarity	NPD7639	Approved
0.6364	Remote Similarity	NPD7640	Approved
0.6337	Remote Similarity	NPD5362	Discontinued
0.6337	Remote Similarity	NPD7154	Phase 3
0.6327	Remote Similarity	NPD4271	Approved
0.6327	Remote Similarity	NPD4268	Approved
0.6321	Remote Similarity	NPD7983	Approved
0.6306	Remote Similarity	NPD5344	Discontinued
0.629	Remote Similarity	NPD7492	Approved
0.625	Remote Similarity	NPD8137	Clinical (unspecified phase)
0.625	Remote Similarity	NPD7524	Approved
0.624	Remote Similarity	NPD6616	Approved
0.623	Remote Similarity	NPD6054	Approved
0.623	Remote Similarity	NPD6059	Approved
0.623	Remote Similarity	NPD6319	Approved
0.6207	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.62	Remote Similarity	NPD5368	Approved
0.619	Remote Similarity	NPD7078	Approved
0.6186	Remote Similarity	NPD6882	Approved
0.6176	Remote Similarity	NPD5331	Approved
0.6176	Remote Similarity	NPD5332	Approved
0.6168	Remote Similarity	NPD7637	Suspended
0.614	Remote Similarity	NPD8170	Clinical (unspecified phase)
0.6139	Remote Similarity	NPD5369	Approved
0.6139	Remote Similarity	NPD4790	Discontinued
0.6132	Remote Similarity	NPD1695	Approved
0.6117	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6117	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6116	Remote Similarity	NPD6009	Approved
0.6111	Remote Similarity	NPD8171	Discontinued
0.6105	Remote Similarity	NPD7532	Clinical (unspecified phase)
0.605	Remote Similarity	NPD8297	Approved
0.6048	Remote Similarity	NPD8274	Clinical (unspecified phase)
0.6048	Remote Similarity	NPD6015	Approved
0.6048	Remote Similarity	NPD6016	Approved
0.6036	Remote Similarity	NPD6084	Phase 2
0.6036	Remote Similarity	NPD6083	Phase 2
0.6019	Remote Similarity	NPD3670	Clinical (unspecified phase)
0.6019	Remote Similarity	NPD3669	Approved
0.6019	Remote Similarity	NPD6695	Phase 3
0.6	Remote Similarity	NPD4632	Approved
0.6	Remote Similarity	NPD4802	Phase 2
0.6	Remote Similarity	NPD4238	Approved
0.6	Remote Similarity	NPD8080	Discontinued
0.6	Remote Similarity	NPD5988	Approved
0.5984	Remote Similarity	NPD7115	Discovery
0.5984	Remote Similarity	NPD8451	Approved
0.5983	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.5982	Remote Similarity	NPD4225	Approved
0.5981	Remote Similarity	NPD6051	Approved
0.5965	Remote Similarity	NPD7632	Discontinued
0.5952	Remote Similarity	NPD6067	Discontinued
0.5948	Remote Similarity	NPD6402	Approved
0.5948	Remote Similarity	NPD6675	Approved
0.5948	Remote Similarity	NPD7128	Approved
0.5948	Remote Similarity	NPD5739	Approved
0.5946	Remote Similarity	NPD4792	Clinical (unspecified phase)
0.5938	Remote Similarity	NPD8448	Approved
0.5938	Remote Similarity	NPD8074	Phase 3
0.5932	Remote Similarity	NPD6372	Approved
0.5932	Remote Similarity	NPD6373	Approved
0.5932	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.5929	Remote Similarity	NPD6648	Approved
0.5926	Remote Similarity	NPD5785	Approved
0.5922	Remote Similarity	NPD4270	Approved
0.5922	Remote Similarity	NPD4269	Approved
0.592	Remote Similarity	NPD8444	Approved
0.5897	Remote Similarity	NPD6685	Approved
0.5872	Remote Similarity	NPD8035	Phase 2
0.5872	Remote Similarity	NPD8034	Phase 2
0.5865	Remote Similarity	NPD4788	Approved
0.5856	Remote Similarity	NPD5695	Phase 3
0.5854	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.5849	Remote Similarity	NPD5786	Approved
0.5847	Remote Similarity	NPD6899	Approved
0.5847	Remote Similarity	NPD6881	Approved
0.5847	Remote Similarity	NPD7320	Approved
0.5842	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.5833	Remote Similarity	NPD6650	Approved
0.5833	Remote Similarity	NPD6649	Approved
0.5827	Remote Similarity	NPD7829	Approved
0.5827	Remote Similarity	NPD7642	Approved
0.5827	Remote Similarity	NPD8328	Phase 3
0.5827	Remote Similarity	NPD7830	Approved
0.5818	Remote Similarity	NPD6399	Phase 3
0.5818	Remote Similarity	NPD5779	Approved
0.5818	Remote Similarity	NPD5778	Approved
0.5806	Remote Similarity	NPD7641	Discontinued
0.5804	Remote Similarity	NPD7839	Suspended
0.5802	Remote Similarity	NPD8392	Approved
0.5802	Remote Similarity	NPD8390	Approved
0.5802	Remote Similarity	NPD8391	Approved
0.5794	Remote Similarity	NPD7750	Discontinued
0.5781	Remote Similarity	NPD8341	Approved
0.5781	Remote Similarity	NPD8340	Approved
0.5781	Remote Similarity	NPD8299	Approved
0.5781	Remote Similarity	NPD8342	Approved
0.5769	Remote Similarity	NPD6033	Approved
0.5766	Remote Similarity	NPD5282	Discontinued
0.5763	Remote Similarity	NPD5697	Approved
0.5763	Remote Similarity	NPD5701	Approved
0.5755	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.5755	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.5755	Remote Similarity	NPD5363	Approved
0.575	Remote Similarity	NPD6883	Approved
0.575	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.575	Remote Similarity	NPD7102	Approved
0.575	Remote Similarity	NPD7290	Approved
0.5745	Remote Similarity	NPD7625	Phase 1
0.5728	Remote Similarity	NPD6931	Approved
0.5728	Remote Similarity	NPD6930	Phase 2
0.5728	Remote Similarity	NPD4252	Approved
0.5714	Remote Similarity	NPD3198	Approved
0.5714	Remote Similarity	NPD6110	Phase 1
0.5703	Remote Similarity	NPD7604	Phase 2
0.5702	Remote Similarity	NPD6847	Approved
0.5702	Remote Similarity	NPD6617	Approved
0.5702	Remote Similarity	NPD5696	Approved
0.5702	Remote Similarity	NPD8130	Phase 1
0.5702	Remote Similarity	NPD6869	Approved
0.569	Remote Similarity	NPD8084	Approved
0.569	Remote Similarity	NPD8138	Approved
0.569	Remote Similarity	NPD8086	Approved
0.569	Remote Similarity	NPD8139	Approved
0.569	Remote Similarity	NPD8082	Approved
0.569	Remote Similarity	NPD8083	Approved
0.569	Remote Similarity	NPD8085	Approved
0.5682	Remote Similarity	NPD5956	Approved
0.5669	Remote Similarity	NPD8266	Approved
0.5669	Remote Similarity	NPD8267	Approved
0.5669	Remote Similarity	NPD8268	Approved
0.5669	Remote Similarity	NPD8269	Approved
0.5669	Remote Similarity	NPD5983	Phase 2
0.5667	Remote Similarity	NPD6012	Approved
0.5667	Remote Similarity	NPD6013	Approved
0.5667	Remote Similarity	NPD6014	Approved
0.5662	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.5656	Remote Similarity	NPD6912	Phase 3
0.5652	Remote Similarity	NPD1145	Discontinued
0.5649	Remote Similarity	NPD8336	Approved
0.5649	Remote Similarity	NPD8337	Approved
0.5644	Remote Similarity	NPD6933	Approved
0.5641	Remote Similarity	NPD8275	Approved
0.5641	Remote Similarity	NPD5765	Approved
0.5641	Remote Similarity	NPD8276	Approved
0.5631	Remote Similarity	NPD6929	Approved
0.562	Remote Similarity	NPD4634	Approved
0.5615	Remote Similarity	NPD6336	Discontinued

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