NPASS Compound

Structure

NPC329834 OpenBabel07101719132D 35 37 0 0 1 0 0 0 0 0999 V2000 -0.4628 -6.5245 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6217 -7.8117 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4662 4.3373 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.6252 3.0501 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9490 -5.1862 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4843 -3.5390 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1570 -6.1644 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9310 2.6900 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2024 -2.0827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2274 -2.8698 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7627 -1.2226 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4138 -6.8335 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6742 3.3592 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6922 -4.5171 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0195 -1.8917 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4593 -1.4135 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.1080 -6.4734 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1389 1.7119 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6433 -4.8261 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -1.8605 -0.6045 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.3864 -4.1570 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6037 0.0646 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.0685 -1.5827 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 0.5189 -1.6215 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.3159 -7.4516 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.0900 1.4029 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.3375 -4.4660 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.6562 -2.3917 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.1785 -3.1789 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.5547 -0.2444 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 -3.8512 -5.8043 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.3958 1.0427 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 13 1 0 0 0 0 2 13 1 0 0 0 0 3 14 1 0 0 0 0 4 14 1 0 0 0 0 5 15 1 0 0 0 0 6 15 1 0 0 0 0 7 13 1 0 0 0 0 7 18 1 0 0 0 0 8 14 1 0 0 0 0 8 19 1 0 0 0 0 9 17 1 0 0 0 0 9 24 1 0 0 0 0 10 16 1 0 0 0 0 10 31 1 0 0 0 0 11 16 2 0 0 0 0 11 32 1 0 0 0 0 12 33 1 0 0 0 0 15 20 1 0 0 0 0 16 24 1 0 0 0 0 17 25 1 1 0 0 0 17 26 1 0 0 0 0 18 27 2 0 0 0 0 18 34 1 0 0 0 0 19 28 2 0 0 0 0 19 35 1 0 0 0 0 20 22 1 0 0 0 0 20 34 1 0 0 0 0 21 23 1 0 0 0 0 21 24 1 6 0 0 0 21 25 1 0 0 0 0 22 29 2 0 0 0 0 22 31 1 0 0 0 0 23 32 1 0 0 0 0 23 35 1 1 0 0 0 24 30 1 1 0 0 0 25 12 1 1 0 0 0 25 33 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	498.25
Volume:	492.643
LogP:	3.205
LogD:	2.31
LogS:	-4.35
# Rotatable Bonds:	13
TPSA:	141.12
# H-Bond Aceptor:	10
# H-Bond Donor:	2
# Rings:	3
# Heavy Atoms:	10

MedChem Properties

QED Drug-Likeness Score:	0.26
Synthetic Accessibility Score:	5.383
Fsp3:	0.8
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.855
MDCK Permeability:	4.481466021388769e-05
Pgp-inhibitor:	0.972
Pgp-substrate:	0.006
Human Intestinal Absorption (HIA):	0.008
20% Bioavailability (F20%):	0.011
30% Bioavailability (F30%):	0.952

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.85
Plasma Protein Binding (PPB):	75.11333465576172%
Volume Distribution (VD):	0.848
Pgp-substrate:	27.048215866088867%

ADMET: Metabolism

CYP1A2-inhibitor:	0.013
CYP1A2-substrate:	0.054
CYP2C19-inhibitor:	0.015
CYP2C19-substrate:	0.644
CYP2C9-inhibitor:	0.101
CYP2C9-substrate:	0.055
CYP2D6-inhibitor:	0.008
CYP2D6-substrate:	0.054
CYP3A4-inhibitor:	0.384
CYP3A4-substrate:	0.398

ADMET: Excretion

Clearance (CL):	7.453
Half-life (T1/2):	0.422

ADMET: Toxicity

hERG Blockers:	0.061
Human Hepatotoxicity (H-HT):	0.655
Drug-inuced Liver Injury (DILI):	0.939
AMES Toxicity:	0.972
Rat Oral Acute Toxicity:	0.812
Maximum Recommended Daily Dose:	0.921
Skin Sensitization:	0.276
Carcinogencity:	0.952
Eye Corrosion:	0.004
Eye Irritation:	0.015
Respiratory Toxicity:	0.346

Download Data

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

Natural Product: NPC329834

Natural Product ID:	NPC329834
*Common Name:**	Jatamanvaltrate L
IUPAC Name:	[(1S,4aR,6S,7R,7aS)-4a,6-dihydroxy-1-(3-methylbutanoyloxy)spiro[1,5,6,7a-tetrahydrocyclopenta[c]pyran-7,2'-oxirane]-4-yl]methyl 3-methyl-2-(3-methylbutanoyloxy)butanoate
Synonyms:
Standard InCHIKey:	ZLGMGWPIAQVIEN-PDQNLLLBSA-N
Standard InCHI:	InChI=1S/C25H38O10/c1-13(2)7-18(27)34-20(15(5)6)22(29)31-10-16-11-32-23(35-19(28)8-14(3)4)21-24(16,30)9-17(26)25(21)12-33-25/h11,13-15,17,20-21,23,26,30H,7-10,12H2,1-6H3/t17-,20?,21-,23-,24-,25+/m0/s1
SMILES:	CC(C)CC(=O)OC1C2C(CC(C23CO3)O)(C(=CO1)COC(=O)C(C(C)C)OC(=O)CC(C)C)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL551501
PubChem CID:	42638126
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[455052]
NPT180	Cell Line	HCT-8	Homo sapiens	IC50	>	10000.0	nM	PMID[455052]
NPT181	Cell Line	Bel-7402	Homo sapiens	IC50	=	7600.0	nM	PMID[455052]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	3400.0	nM	PMID[455052]

☑ 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 NPC329834 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	259
0.1-0.2	2113
0.2-0.3	6675
0.3-0.4	14901
0.4-0.5	9616
0.5-0.6	7149
0.6-0.7	1791
0.7-0.8	167
0.8-0.85	7
0.85-0.9	5
0.9-0.95	11
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9789	High Similarity	NPC216911
0.9789	High Similarity	NPC476228
0.9684	High Similarity	NPC476211
0.9684	High Similarity	NPC476320
0.9583	High Similarity	NPC476230
0.9583	High Similarity	NPC27474
0.9474	High Similarity	NPC86843
0.9388	High Similarity	NPC329704
0.9368	High Similarity	NPC284063
0.9263	High Similarity	NPC93869
0.9263	High Similarity	NPC6765
0.9158	High Similarity	NPC274588
0.8969	High Similarity	NPC170527
0.8947	High Similarity	NPC66504
0.8932	High Similarity	NPC208307
0.875	High Similarity	NPC235051
0.8491	Intermediate Similarity	NPC193741
0.8333	Intermediate Similarity	NPC475924
0.8333	Intermediate Similarity	NPC475851
0.8269	Intermediate Similarity	NPC37240
0.8208	Intermediate Similarity	NPC148270
0.8208	Intermediate Similarity	NPC197813
0.8208	Intermediate Similarity	NPC80338
0.8173	Intermediate Similarity	NPC35185
0.8173	Intermediate Similarity	NPC177013
0.8173	Intermediate Similarity	NPC4899
0.8173	Intermediate Similarity	NPC474730
0.8131	Intermediate Similarity	NPC110701
0.8113	Intermediate Similarity	NPC127235
0.8113	Intermediate Similarity	NPC170432
0.8095	Intermediate Similarity	NPC475928
0.8077	Intermediate Similarity	NPC20673
0.8077	Intermediate Similarity	NPC3488
0.8077	Intermediate Similarity	NPC287539
0.8	Intermediate Similarity	NPC294643
0.8	Intermediate Similarity	NPC473150
0.8	Intermediate Similarity	NPC274274
0.7981	Intermediate Similarity	NPC244878
0.798	Intermediate Similarity	NPC93190
0.7885	Intermediate Similarity	NPC151093
0.783	Intermediate Similarity	NPC106668
0.78	Intermediate Similarity	NPC22918
0.78	Intermediate Similarity	NPC50464
0.7757	Intermediate Similarity	NPC27687
0.7757	Intermediate Similarity	NPC473148
0.7745	Intermediate Similarity	NPC470187
0.7736	Intermediate Similarity	NPC219038
0.7736	Intermediate Similarity	NPC98859
0.7736	Intermediate Similarity	NPC4637
0.77	Intermediate Similarity	NPC148534
0.7664	Intermediate Similarity	NPC214714
0.7664	Intermediate Similarity	NPC200672
0.7664	Intermediate Similarity	NPC471599
0.7664	Intermediate Similarity	NPC304163
0.7647	Intermediate Similarity	NPC276298
0.7619	Intermediate Similarity	NPC236580
0.7619	Intermediate Similarity	NPC261372
0.7619	Intermediate Similarity	NPC263674
0.7619	Intermediate Similarity	NPC304445
0.7619	Intermediate Similarity	NPC58267
0.76	Intermediate Similarity	NPC258501
0.7596	Intermediate Similarity	NPC241407
0.7596	Intermediate Similarity	NPC291709
0.757	Intermediate Similarity	NPC67296
0.757	Intermediate Similarity	NPC26557
0.7547	Intermediate Similarity	NPC90819
0.7547	Intermediate Similarity	NPC469919
0.7547	Intermediate Similarity	NPC469918
0.7547	Intermediate Similarity	NPC117066
0.7547	Intermediate Similarity	NPC223700
0.7547	Intermediate Similarity	NPC124181
0.7547	Intermediate Similarity	NPC96399
0.7524	Intermediate Similarity	NPC161293
0.7524	Intermediate Similarity	NPC474297
0.75	Intermediate Similarity	NPC171484
0.75	Intermediate Similarity	NPC475956
0.75	Intermediate Similarity	NPC252242
0.75	Intermediate Similarity	NPC149018
0.7455	Intermediate Similarity	NPC470980
0.7455	Intermediate Similarity	NPC44004
0.7453	Intermediate Similarity	NPC153559
0.7436	Intermediate Similarity	NPC219656
0.7431	Intermediate Similarity	NPC474783
0.7431	Intermediate Similarity	NPC232515
0.7431	Intermediate Similarity	NPC260809
0.7407	Intermediate Similarity	NPC471767
0.7383	Intermediate Similarity	NPC249171
0.7383	Intermediate Similarity	NPC49833
0.7383	Intermediate Similarity	NPC474957
0.7383	Intermediate Similarity	NPC274458
0.7383	Intermediate Similarity	NPC473307
0.7383	Intermediate Similarity	NPC79449
0.7368	Intermediate Similarity	NPC98038
0.7368	Intermediate Similarity	NPC313921
0.7358	Intermediate Similarity	NPC98165
0.7339	Intermediate Similarity	NPC475986
0.7339	Intermediate Similarity	NPC250594
0.7339	Intermediate Similarity	NPC80144
0.7333	Intermediate Similarity	NPC63897
0.7315	Intermediate Similarity	NPC130792
0.7315	Intermediate Similarity	NPC471381
0.7315	Intermediate Similarity	NPC186861
0.7311	Intermediate Similarity	NPC233500
0.7304	Intermediate Similarity	NPC287075
0.7304	Intermediate Similarity	NPC101965
0.7304	Intermediate Similarity	NPC101400
0.73	Intermediate Similarity	NPC98276
0.73	Intermediate Similarity	NPC259296
0.729	Intermediate Similarity	NPC347923
0.729	Intermediate Similarity	NPC474182
0.729	Intermediate Similarity	NPC470684
0.729	Intermediate Similarity	NPC470683
0.729	Intermediate Similarity	NPC472290
0.729	Intermediate Similarity	NPC182811
0.729	Intermediate Similarity	NPC476057
0.7288	Intermediate Similarity	NPC477092
0.7264	Intermediate Similarity	NPC240838
0.7264	Intermediate Similarity	NPC472873
0.725	Intermediate Similarity	NPC196130
0.7241	Intermediate Similarity	NPC106446
0.7222	Intermediate Similarity	NPC45125
0.7222	Intermediate Similarity	NPC37866
0.7212	Intermediate Similarity	NPC246173
0.7207	Intermediate Similarity	NPC86095
0.7203	Intermediate Similarity	NPC474286
0.7203	Intermediate Similarity	NPC475130
0.7203	Intermediate Similarity	NPC475401
0.7193	Intermediate Similarity	NPC86217
0.719	Intermediate Similarity	NPC219804
0.7184	Intermediate Similarity	NPC233997
0.7182	Intermediate Similarity	NPC470972
0.7168	Intermediate Similarity	NPC117604
0.7157	Intermediate Similarity	NPC471480
0.7157	Intermediate Similarity	NPC322922
0.7157	Intermediate Similarity	NPC321812
0.7156	Intermediate Similarity	NPC22149
0.7156	Intermediate Similarity	NPC473146
0.7156	Intermediate Similarity	NPC306344
0.7156	Intermediate Similarity	NPC255677
0.7143	Intermediate Similarity	NPC54737
0.7143	Intermediate Similarity	NPC85670
0.713	Intermediate Similarity	NPC471150
0.713	Intermediate Similarity	NPC474313
0.712	Intermediate Similarity	NPC213634
0.7119	Intermediate Similarity	NPC475305
0.7117	Intermediate Similarity	NPC267869
0.7117	Intermediate Similarity	NPC284929
0.7117	Intermediate Similarity	NPC197541
0.7117	Intermediate Similarity	NPC234304
0.7117	Intermediate Similarity	NPC118761
0.7105	Intermediate Similarity	NPC305939
0.7105	Intermediate Similarity	NPC139838
0.7105	Intermediate Similarity	NPC59489
0.7103	Intermediate Similarity	NPC167893
0.7094	Intermediate Similarity	NPC265290
0.7094	Intermediate Similarity	NPC305044
0.7091	Intermediate Similarity	NPC298255
0.7091	Intermediate Similarity	NPC28304
0.7087	Intermediate Similarity	NPC475376
0.7087	Intermediate Similarity	NPC471234
0.7087	Intermediate Similarity	NPC31349
0.708	Intermediate Similarity	NPC470170
0.708	Intermediate Similarity	NPC472263
0.708	Intermediate Similarity	NPC470169
0.708	Intermediate Similarity	NPC469959
0.708	Intermediate Similarity	NPC469957
0.708	Intermediate Similarity	NPC108682
0.7075	Intermediate Similarity	NPC258216
0.7075	Intermediate Similarity	NPC320089
0.7075	Intermediate Similarity	NPC474835
0.7075	Intermediate Similarity	NPC475788
0.7075	Intermediate Similarity	NPC472195
0.7075	Intermediate Similarity	NPC238090
0.7075	Intermediate Similarity	NPC472196
0.7071	Intermediate Similarity	NPC475946
0.7068	Intermediate Similarity	NPC194854
0.7068	Intermediate Similarity	NPC48813
0.7064	Intermediate Similarity	NPC472015
0.7059	Intermediate Similarity	NPC472080
0.7048	Intermediate Similarity	NPC117596
0.7048	Intermediate Similarity	NPC270908
0.7048	Intermediate Similarity	NPC120021
0.7048	Intermediate Similarity	NPC65665
0.7048	Intermediate Similarity	NPC216826
0.7048	Intermediate Similarity	NPC470573
0.7048	Intermediate Similarity	NPC231710
0.7043	Intermediate Similarity	NPC106760
0.7037	Intermediate Similarity	NPC54731
0.7034	Intermediate Similarity	NPC277583
0.7031	Intermediate Similarity	NPC219058
0.7031	Intermediate Similarity	NPC256618
0.703	Intermediate Similarity	NPC474266
0.7027	Intermediate Similarity	NPC78127
0.7027	Intermediate Similarity	NPC13171
0.7027	Intermediate Similarity	NPC471757
0.7027	Intermediate Similarity	NPC49393
0.7027	Intermediate Similarity	NPC195510
0.7027	Intermediate Similarity	NPC222062
0.7027	Intermediate Similarity	NPC94919
0.7025	Intermediate Similarity	NPC133506

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 NPC329834 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	289
0.1-0.2	2848
0.2-0.3	3736
0.3-0.4	1570
0.4-0.5	471
0.5-0.6	202
0.6-0.7	34
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
0.7025	Intermediate Similarity	NPD7503	Approved
0.7009	Intermediate Similarity	NPD8133	Approved
0.6838	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6777	Remote Similarity	NPD7327	Approved
0.6777	Remote Similarity	NPD7328	Approved
0.6762	Remote Similarity	NPD4250	Approved
0.6762	Remote Similarity	NPD4251	Approved
0.6748	Remote Similarity	NPD8033	Approved
0.6729	Remote Similarity	NPD46	Approved
0.6729	Remote Similarity	NPD6698	Approved
0.6724	Remote Similarity	NPD6686	Approved
0.6721	Remote Similarity	NPD7516	Approved
0.6667	Remote Similarity	NPD4249	Approved
0.6667	Remote Similarity	NPD8377	Approved
0.6667	Remote Similarity	NPD8294	Approved
0.6667	Remote Similarity	NPD7507	Approved
0.6639	Remote Similarity	NPD6053	Discontinued
0.6638	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6613	Remote Similarity	NPD8378	Approved
0.6613	Remote Similarity	NPD8296	Approved
0.6613	Remote Similarity	NPD8380	Approved
0.6613	Remote Similarity	NPD8335	Approved
0.6613	Remote Similarity	NPD8379	Approved
0.6609	Remote Similarity	NPD4056	Clinical (unspecified phase)
0.6609	Remote Similarity	NPD4057	Clinical (unspecified phase)
0.6574	Remote Similarity	NPD7838	Discovery
0.6512	Remote Similarity	NPD7319	Approved
0.6496	Remote Similarity	NPD6412	Phase 2
0.6484	Remote Similarity	NPD8293	Discontinued
0.6471	Remote Similarity	NPD6371	Approved
0.646	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6434	Remote Similarity	NPD7736	Approved
0.6429	Remote Similarity	NPD6370	Approved
0.6415	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6408	Remote Similarity	NPD4819	Approved
0.6408	Remote Similarity	NPD4820	Approved
0.6408	Remote Similarity	NPD4821	Approved
0.6408	Remote Similarity	NPD4822	Approved
0.6408	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6349	Remote Similarity	NPD8513	Phase 3
0.6348	Remote Similarity	NPD5344	Discontinued
0.6328	Remote Similarity	NPD7492	Approved
0.6279	Remote Similarity	NPD6616	Approved
0.627	Remote Similarity	NPD6054	Approved
0.627	Remote Similarity	NPD6059	Approved
0.627	Remote Similarity	NPD6319	Approved
0.6231	Remote Similarity	NPD7078	Approved
0.623	Remote Similarity	NPD6882	Approved
0.6226	Remote Similarity	NPD7154	Phase 3
0.622	Remote Similarity	NPD8516	Approved
0.622	Remote Similarity	NPD8515	Approved
0.622	Remote Similarity	NPD8517	Approved
0.6214	Remote Similarity	NPD4268	Approved
0.6214	Remote Similarity	NPD4271	Approved
0.616	Remote Similarity	NPD6009	Approved
0.614	Remote Similarity	NPD4792	Clinical (unspecified phase)
0.6132	Remote Similarity	NPD6435	Approved
0.6121	Remote Similarity	NPD7640	Approved
0.6121	Remote Similarity	NPD7639	Approved
0.6098	Remote Similarity	NPD8297	Approved
0.6094	Remote Similarity	NPD6015	Approved
0.6094	Remote Similarity	NPD6016	Approved
0.6094	Remote Similarity	NPD8274	Clinical (unspecified phase)
0.6087	Remote Similarity	NPD6084	Phase 2
0.6087	Remote Similarity	NPD6083	Phase 2
0.6075	Remote Similarity	NPD5362	Discontinued
0.6071	Remote Similarity	NPD7983	Approved
0.6047	Remote Similarity	NPD8080	Discontinued
0.6047	Remote Similarity	NPD5988	Approved
0.6036	Remote Similarity	NPD1695	Approved
0.6034	Remote Similarity	NPD7638	Approved
0.6032	Remote Similarity	NPD7115	Discovery
0.6	Remote Similarity	NPD7524	Approved
0.6	Remote Similarity	NPD6675	Approved
0.6	Remote Similarity	NPD5739	Approved
0.6	Remote Similarity	NPD7128	Approved
0.6	Remote Similarity	NPD6402	Approved
0.5984	Remote Similarity	NPD6372	Approved
0.5984	Remote Similarity	NPD6373	Approved
0.5983	Remote Similarity	NPD6648	Approved
0.5943	Remote Similarity	NPD5368	Approved
0.5929	Remote Similarity	NPD7637	Suspended
0.5926	Remote Similarity	NPD5332	Approved
0.5926	Remote Similarity	NPD6110	Phase 1
0.5926	Remote Similarity	NPD5331	Approved
0.592	Remote Similarity	NPD4632	Approved
0.5913	Remote Similarity	NPD5695	Phase 3
0.5906	Remote Similarity	NPD8137	Clinical (unspecified phase)
0.5906	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.5902	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.5902	Remote Similarity	NPD6881	Approved
0.5902	Remote Similarity	NPD6899	Approved
0.5902	Remote Similarity	NPD7320	Approved
0.5888	Remote Similarity	NPD4790	Discontinued
0.5887	Remote Similarity	NPD6649	Approved
0.5887	Remote Similarity	NPD6650	Approved
0.5878	Remote Similarity	NPD7604	Phase 2
0.5878	Remote Similarity	NPD8328	Phase 3
0.5872	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.5872	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.5854	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.5854	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.5821	Remote Similarity	NPD6033	Approved
0.582	Remote Similarity	NPD5701	Approved
0.582	Remote Similarity	NPD5697	Approved
0.5806	Remote Similarity	NPD7290	Approved
0.5806	Remote Similarity	NPD7102	Approved
0.5806	Remote Similarity	NPD6883	Approved
0.5798	Remote Similarity	NPD1700	Approved
0.5785	Remote Similarity	NPD8170	Clinical (unspecified phase)
0.578	Remote Similarity	NPD6695	Phase 3
0.5763	Remote Similarity	NPD4225	Approved
0.5763	Remote Similarity	NPD5696	Approved
0.576	Remote Similarity	NPD6617	Approved
0.576	Remote Similarity	NPD6869	Approved
0.576	Remote Similarity	NPD8130	Phase 1
0.576	Remote Similarity	NPD6847	Approved
0.5758	Remote Similarity	NPD7829	Approved
0.5758	Remote Similarity	NPD7830	Approved
0.5758	Remote Similarity	NPD7642	Approved
0.575	Remote Similarity	NPD7632	Discontinued
0.5746	Remote Similarity	NPD8074	Phase 3
0.5741	Remote Similarity	NPD5369	Approved
0.5739	Remote Similarity	NPD8171	Discontinued
0.5735	Remote Similarity	NPD5956	Approved
0.5726	Remote Similarity	NPD6014	Approved
0.5726	Remote Similarity	NPD6013	Approved
0.5726	Remote Similarity	NPD6012	Approved
0.5725	Remote Similarity	NPD5983	Phase 2
0.5714	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.5702	Remote Similarity	NPD5785	Approved
0.5691	Remote Similarity	NPD6685	Approved
0.569	Remote Similarity	NPD5282	Discontinued
0.5688	Remote Similarity	NPD4269	Approved
0.5688	Remote Similarity	NPD4270	Approved
0.5686	Remote Similarity	NPD7532	Clinical (unspecified phase)
0.568	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.5676	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.5672	Remote Similarity	NPD6336	Discontinued
0.5672	Remote Similarity	NPD8451	Approved
0.5652	Remote Similarity	NPD5693	Phase 1
0.5645	Remote Similarity	NPD6011	Approved
0.5639	Remote Similarity	NPD6067	Discontinued
0.5636	Remote Similarity	NPD3669	Approved
0.5636	Remote Similarity	NPD3670	Clinical (unspecified phase)
0.5635	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.563	Remote Similarity	NPD8448	Approved
0.5625	Remote Similarity	NPD5786	Approved
0.5614	Remote Similarity	NPD6051	Approved
0.5607	Remote Similarity	NPD4238	Approved
0.5607	Remote Similarity	NPD4802	Phase 2
0.5607	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.5606	Remote Similarity	NPD8444	Approved
0.5603	Remote Similarity	NPD5778	Approved
0.5603	Remote Similarity	NPD5779	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