NPASS Compound

Structure

NPC175293 OpenBabel07101719122D 21 23 0 0 1 0 0 0 0 0999 V2000 3.5491 2.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3090 2.5691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.0132 -0.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6831 -0.6910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4152 1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8171 1.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5491 -0.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8171 -0.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5491 1.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 1.6180 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.1472 0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4152 0.3090 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.9511 1.3090 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.6831 1.3090 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.9511 0.3090 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.5878 0.8090 0.0000 C 0 0 0 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 6.1472 1.3090 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.5878 0.8090 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.2812 -0.1910 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 9 2 0 0 0 0 2 10 2 0 0 0 0 3 11 1 0 0 0 0 5 9 1 0 0 0 0 5 12 1 0 0 0 0 6 14 1 0 0 0 0 7 12 1 0 0 0 0 7 17 1 0 0 0 0 8 17 1 0 0 0 0 9 14 1 0 0 0 0 10 13 1 0 0 0 0 10 16 1 0 0 0 0 11 18 2 0 0 0 0 11 20 1 0 0 0 0 12 20 1 6 0 0 0 13 6 1 1 0 0 0 13 15 1 0 0 0 0 14 17 1 1 0 0 0 15 8 1 1 0 0 0 15 21 1 0 0 0 0 16 19 2 0 0 0 0 16 21 1 0 0 0 0 17 4 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	290.15
Volume:	301.534
LogP:	2.497
LogD:	2.218
LogS:	-3.342
# Rotatable Bonds:	2
TPSA:	52.6
# H-Bond Aceptor:	4
# H-Bond Donor:	0
# Rings:	3
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.423
Synthetic Accessibility Score:	4.533
Fsp3:	0.647
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	2
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.738
MDCK Permeability:	7.36035144655034e-05
Pgp-inhibitor:	0.006
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.006
20% Bioavailability (F20%):	0.014
30% Bioavailability (F30%):	0.008

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.02
Plasma Protein Binding (PPB):	73.7197036743164%
Volume Distribution (VD):	1.142
Pgp-substrate:	31.78425407409668%

ADMET: Metabolism

CYP1A2-inhibitor:	0.072
CYP1A2-substrate:	0.079
CYP2C19-inhibitor:	0.077
CYP2C19-substrate:	0.227
CYP2C9-inhibitor:	0.337
CYP2C9-substrate:	0.168
CYP2D6-inhibitor:	0.013
CYP2D6-substrate:	0.158
CYP3A4-inhibitor:	0.571
CYP3A4-substrate:	0.291

ADMET: Excretion

Clearance (CL):	3.427
Half-life (T1/2):	0.574

ADMET: Toxicity

hERG Blockers:	0.01
Human Hepatotoxicity (H-HT):	0.878
Drug-inuced Liver Injury (DILI):	0.95
AMES Toxicity:	0.531
Rat Oral Acute Toxicity:	0.723
Maximum Recommended Daily Dose:	0.966
Skin Sensitization:	0.797
Carcinogencity:	0.513
Eye Corrosion:	0.132
Eye Irritation:	0.59
Respiratory Toxicity:	0.953

Download Data

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

Natural Product: NPC175293

Natural Product ID:	NPC175293
*Common Name:**	Ivalin Acetate
IUPAC Name:	[(3aR,4aS,7S,8aR,9aR)-8a-methyl-3,5-dimethylidene-2-oxo-3a,4,4a,6,7,8,9,9a-octahydrobenzo[f][1]benzofuran-7-yl] acetate
Synonyms:
Standard InCHIKey:	QPWCHXDSBJOZCP-LVNYTYFRSA-N
Standard InCHI:	InChI=1S/C17H22O4/c1-9-5-12(20-11(3)18)7-17(4)8-15-13(6-14(9)17)10(2)16(19)21-15/h12-15H,1-2,5-8H2,3-4H3/t12-,13+,14-,15+,17+/m0/s1
SMILES:	C=C1C[C@@H](C[C@]2(C)C[C@@H]3[C@H](C[C@@H]12)C(=C)C(=O)O3)OC(=O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2380792
PubChem CID:	181263
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001283] Terpene lactones [CHEMONTID:0001543] Sesquiterpene lactones [CHEMONTID:0001772] Eudesmanolides, secoeudesmanolides, 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
NPO23805	Arnica nevadensis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23501116]
NPO23805	Arnica nevadensis	Species	Asteraceae	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	3

Activity Type	# Activity
Individual Protein	2
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT840	Individual Protein	Transcriptional activator Myb	Gallus gallus	IC50	=	22080.05	nM	PMID[564930]
NPT27	Others	Unspecified		IC50	>	30000.0	nM	PMID[564930]
NPT840	Individual Protein	Transcriptional activator Myb	Gallus gallus	IC50	=	22080.0	nM	PMID[564930]

☑ 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 NPC175293 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	215
0.1-0.2	1514
0.2-0.3	5205
0.3-0.4	11731
0.4-0.5	9813
0.5-0.6	6172
0.6-0.7	6245
0.7-0.8	1642
0.8-0.85	112
0.85-0.9	31
0.9-0.95	14
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9643	High Similarity	NPC475776
0.9383	High Similarity	NPC226988
0.9294	High Similarity	NPC116620
0.9205	High Similarity	NPC157686
0.9205	High Similarity	NPC259042
0.9157	High Similarity	NPC470011
0.9101	High Similarity	NPC473964
0.9091	High Similarity	NPC473434
0.9091	High Similarity	NPC148000
0.9091	High Similarity	NPC469596
0.9091	High Similarity	NPC471446
0.9091	High Similarity	NPC474841
0.9091	High Similarity	NPC225474
0.9	High Similarity	NPC474921
0.9	High Similarity	NPC473963
0.8929	High Similarity	NPC219011
0.8889	High Similarity	NPC93245
0.8876	High Similarity	NPC24861
0.8837	High Similarity	NPC181103
0.8837	High Similarity	NPC305029
0.881	High Similarity	NPC194637
0.8804	High Similarity	NPC47024
0.8795	High Similarity	NPC38642
0.8778	High Similarity	NPC90014
0.8778	High Similarity	NPC56369
0.8721	High Similarity	NPC185638
0.8721	High Similarity	NPC9231
0.8721	High Similarity	NPC85698
0.8706	High Similarity	NPC97505
0.8696	High Similarity	NPC476806
0.8696	High Similarity	NPC476807
0.8681	High Similarity	NPC284518
0.8642	High Similarity	NPC92489
0.8621	High Similarity	NPC470012
0.8587	High Similarity	NPC136781
0.8556	High Similarity	NPC475657
0.8526	High Similarity	NPC61442
0.8526	High Similarity	NPC254202
0.8511	High Similarity	NPC475958
0.8506	High Similarity	NPC477920
0.8495	Intermediate Similarity	NPC216478
0.8478	Intermediate Similarity	NPC228766
0.8478	Intermediate Similarity	NPC165528
0.8478	Intermediate Similarity	NPC307164
0.8462	Intermediate Similarity	NPC224410
0.8462	Intermediate Similarity	NPC66581
0.8462	Intermediate Similarity	NPC100257
0.8438	Intermediate Similarity	NPC477127
0.8427	Intermediate Similarity	NPC288699
0.8427	Intermediate Similarity	NPC471043
0.8427	Intermediate Similarity	NPC194642
0.8427	Intermediate Similarity	NPC73995
0.8421	Intermediate Similarity	NPC164551
0.8353	Intermediate Similarity	NPC47635
0.8353	Intermediate Similarity	NPC475951
0.8352	Intermediate Similarity	NPC147272
0.8333	Intermediate Similarity	NPC99510
0.8333	Intermediate Similarity	NPC152467
0.8333	Intermediate Similarity	NPC158488
0.8316	Intermediate Similarity	NPC242666
0.8316	Intermediate Similarity	NPC308824
0.8315	Intermediate Similarity	NPC215831
0.8315	Intermediate Similarity	NPC477128
0.8298	Intermediate Similarity	NPC252295
0.8298	Intermediate Similarity	NPC473155
0.8265	Intermediate Similarity	NPC78966
0.8265	Intermediate Similarity	NPC284732
0.8261	Intermediate Similarity	NPC477129
0.8261	Intermediate Similarity	NPC477130
0.8261	Intermediate Similarity	NPC57117
0.8256	Intermediate Similarity	NPC178676
0.8242	Intermediate Similarity	NPC470230
0.8242	Intermediate Similarity	NPC186363
0.8242	Intermediate Similarity	NPC49420
0.8242	Intermediate Similarity	NPC233345
0.8211	Intermediate Similarity	NPC471413
0.8211	Intermediate Similarity	NPC476303
0.8211	Intermediate Similarity	NPC473219
0.8211	Intermediate Similarity	NPC470906
0.8211	Intermediate Similarity	NPC470761
0.8191	Intermediate Similarity	NPC474395
0.8182	Intermediate Similarity	NPC189075
0.8182	Intermediate Similarity	NPC37628
0.8182	Intermediate Similarity	NPC275539
0.8172	Intermediate Similarity	NPC183012
0.8171	Intermediate Similarity	NPC55508
0.8152	Intermediate Similarity	NPC199543
0.8144	Intermediate Similarity	NPC72842
0.8144	Intermediate Similarity	NPC156681
0.814	Intermediate Similarity	NPC209318
0.814	Intermediate Similarity	NPC223330
0.8132	Intermediate Similarity	NPC153853
0.8125	Intermediate Similarity	NPC471412
0.8125	Intermediate Similarity	NPC111292
0.8118	Intermediate Similarity	NPC263951
0.8111	Intermediate Similarity	NPC50847
0.8111	Intermediate Similarity	NPC226863
0.8111	Intermediate Similarity	NPC277771
0.8105	Intermediate Similarity	NPC16911
0.8105	Intermediate Similarity	NPC469986
0.8105	Intermediate Similarity	NPC78427
0.81	Intermediate Similarity	NPC474243
0.81	Intermediate Similarity	NPC112457
0.809	Intermediate Similarity	NPC471042
0.8085	Intermediate Similarity	NPC29410
0.8085	Intermediate Similarity	NPC256227
0.8085	Intermediate Similarity	NPC134072
0.8085	Intermediate Similarity	NPC200054
0.8085	Intermediate Similarity	NPC234993
0.8081	Intermediate Similarity	NPC110496
0.8068	Intermediate Similarity	NPC159635
0.8068	Intermediate Similarity	NPC139566
0.8065	Intermediate Similarity	NPC470697
0.8065	Intermediate Similarity	NPC47853
0.8065	Intermediate Similarity	NPC250075
0.8065	Intermediate Similarity	NPC475118
0.8061	Intermediate Similarity	NPC283850
0.8043	Intermediate Similarity	NPC473944
0.8043	Intermediate Similarity	NPC165180
0.8043	Intermediate Similarity	NPC72845
0.8043	Intermediate Similarity	NPC198054
0.8041	Intermediate Similarity	NPC31058
0.8041	Intermediate Similarity	NPC273005
0.8041	Intermediate Similarity	NPC162973
0.8041	Intermediate Similarity	NPC476081
0.8041	Intermediate Similarity	NPC469606
0.8021	Intermediate Similarity	NPC287676
0.802	Intermediate Similarity	NPC253906
0.8	Intermediate Similarity	NPC474343
0.8	Intermediate Similarity	NPC96839
0.8	Intermediate Similarity	NPC255082
0.798	Intermediate Similarity	NPC469607
0.7979	Intermediate Similarity	NPC470232
0.7979	Intermediate Similarity	NPC280877
0.7979	Intermediate Similarity	NPC98639
0.7979	Intermediate Similarity	NPC470229
0.7978	Intermediate Similarity	NPC110405
0.7959	Intermediate Similarity	NPC36688
0.7959	Intermediate Similarity	NPC476237
0.7959	Intermediate Similarity	NPC176883
0.7959	Intermediate Similarity	NPC120321
0.7959	Intermediate Similarity	NPC221421
0.7957	Intermediate Similarity	NPC475700
0.7957	Intermediate Similarity	NPC474185
0.7957	Intermediate Similarity	NPC139692
0.7955	Intermediate Similarity	NPC22611
0.7955	Intermediate Similarity	NPC170862
0.7938	Intermediate Similarity	NPC289148
0.7938	Intermediate Similarity	NPC163963
0.7938	Intermediate Similarity	NPC52899
0.7935	Intermediate Similarity	NPC212679
0.7935	Intermediate Similarity	NPC220454
0.7935	Intermediate Similarity	NPC469595
0.7917	Intermediate Similarity	NPC28864
0.7917	Intermediate Similarity	NPC20479
0.7917	Intermediate Similarity	NPC38296
0.7917	Intermediate Similarity	NPC89099
0.7917	Intermediate Similarity	NPC162459
0.7917	Intermediate Similarity	NPC471038
0.7917	Intermediate Similarity	NPC38471
0.7917	Intermediate Similarity	NPC98837
0.7917	Intermediate Similarity	NPC23364
0.7912	Intermediate Similarity	NPC106332
0.79	Intermediate Similarity	NPC133422
0.79	Intermediate Similarity	NPC302788
0.79	Intermediate Similarity	NPC180744
0.7895	Intermediate Similarity	NPC29952
0.7895	Intermediate Similarity	NPC329910
0.7879	Intermediate Similarity	NPC470297
0.7872	Intermediate Similarity	NPC476722
0.7872	Intermediate Similarity	NPC470386
0.7872	Intermediate Similarity	NPC470385
0.7864	Intermediate Similarity	NPC194951
0.7864	Intermediate Similarity	NPC12046
0.7857	Intermediate Similarity	NPC304832
0.7857	Intermediate Similarity	NPC246736
0.7857	Intermediate Similarity	NPC58329
0.7857	Intermediate Similarity	NPC170615
0.7857	Intermediate Similarity	NPC148628
0.7857	Intermediate Similarity	NPC76866
0.7857	Intermediate Similarity	NPC286519
0.7857	Intermediate Similarity	NPC165250
0.7857	Intermediate Similarity	NPC88203
0.7857	Intermediate Similarity	NPC214946
0.7849	Intermediate Similarity	NPC476934
0.7841	Intermediate Similarity	NPC246076
0.7841	Intermediate Similarity	NPC200513
0.7841	Intermediate Similarity	NPC476458
0.7841	Intermediate Similarity	NPC258153
0.7835	Intermediate Similarity	NPC293866
0.7835	Intermediate Similarity	NPC267921
0.7835	Intermediate Similarity	NPC476933
0.7826	Intermediate Similarity	NPC474396
0.7826	Intermediate Similarity	NPC50488
0.7816	Intermediate Similarity	NPC469802
0.7816	Intermediate Similarity	NPC195424
0.7816	Intermediate Similarity	NPC170038
0.7812	Intermediate Similarity	NPC38530
0.7812	Intermediate Similarity	NPC110937
0.7812	Intermediate Similarity	NPC10864

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 NPC175293 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	185
0.1-0.2	1924
0.2-0.3	3925
0.3-0.4	2056
0.4-0.5	616
0.5-0.6	202
0.6-0.7	212
0.7-0.8	30
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
0.7841	Intermediate Similarity	NPD4752	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD1694	Approved
0.7732	Intermediate Similarity	NPD7638	Approved
0.7653	Intermediate Similarity	NPD7640	Approved
0.7653	Intermediate Similarity	NPD7639	Approved
0.7624	Intermediate Similarity	NPD6008	Approved
0.7551	Intermediate Similarity	NPD4225	Approved
0.7474	Intermediate Similarity	NPD8034	Phase 2
0.7474	Intermediate Similarity	NPD8035	Phase 2
0.7379	Intermediate Similarity	NPD5954	Clinical (unspecified phase)
0.732	Intermediate Similarity	NPD7900	Approved
0.732	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.7216	Intermediate Similarity	NPD6399	Phase 3
0.7204	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.717	Intermediate Similarity	NPD5955	Clinical (unspecified phase)
0.7157	Intermediate Similarity	NPD7632	Discontinued
0.7143	Intermediate Similarity	NPD7748	Approved
0.7128	Intermediate Similarity	NPD7521	Approved
0.7128	Intermediate Similarity	NPD7334	Approved
0.7128	Intermediate Similarity	NPD7146	Approved
0.7128	Intermediate Similarity	NPD6684	Approved
0.7128	Intermediate Similarity	NPD5330	Approved
0.7128	Intermediate Similarity	NPD6409	Approved
0.71	Intermediate Similarity	NPD7902	Approved
0.7075	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.7071	Intermediate Similarity	NPD6356	Clinical (unspecified phase)
0.7053	Intermediate Similarity	NPD3573	Approved
0.6981	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6981	Remote Similarity	NPD6686	Approved
0.6979	Remote Similarity	NPD5737	Approved
0.6979	Remote Similarity	NPD6672	Approved
0.6979	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6979	Remote Similarity	NPD6903	Approved
0.6947	Remote Similarity	NPD3618	Phase 1
0.6939	Remote Similarity	NPD5693	Phase 1
0.6939	Remote Similarity	NPD7515	Phase 2
0.6937	Remote Similarity	NPD7115	Discovery
0.6907	Remote Similarity	NPD1695	Approved
0.6842	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.6818	Remote Similarity	NPD8133	Approved
0.6813	Remote Similarity	NPD6118	Approved
0.6813	Remote Similarity	NPD6114	Approved
0.6813	Remote Similarity	NPD6115	Approved
0.6813	Remote Similarity	NPD6697	Approved
0.68	Remote Similarity	NPD6001	Approved
0.6737	Remote Similarity	NPD3668	Phase 3
0.6729	Remote Similarity	NPD5697	Approved
0.6702	Remote Similarity	NPD3667	Approved
0.6667	Remote Similarity	NPD6881	Approved
0.6667	Remote Similarity	NPD6011	Approved
0.6667	Remote Similarity	NPD4632	Approved
0.6667	Remote Similarity	NPD6899	Approved
0.6636	Remote Similarity	NPD6402	Approved
0.6636	Remote Similarity	NPD7128	Approved
0.6636	Remote Similarity	NPD5739	Approved
0.6636	Remote Similarity	NPD6649	Approved
0.6636	Remote Similarity	NPD6650	Approved
0.6636	Remote Similarity	NPD6675	Approved
0.6606	Remote Similarity	NPD6014	Approved
0.6606	Remote Similarity	NPD6372	Approved
0.6606	Remote Similarity	NPD6013	Approved
0.6606	Remote Similarity	NPD6373	Approved
0.6606	Remote Similarity	NPD6012	Approved
0.66	Remote Similarity	NPD6079	Approved
0.6593	Remote Similarity	NPD6117	Approved
0.6574	Remote Similarity	NPD5701	Approved
0.6569	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6566	Remote Similarity	NPD5328	Approved
0.6566	Remote Similarity	NPD6051	Approved
0.6566	Remote Similarity	NPD6904	Approved
0.6566	Remote Similarity	NPD6673	Approved
0.6566	Remote Similarity	NPD6080	Approved
0.6562	Remote Similarity	NPD4786	Approved
0.6545	Remote Similarity	NPD6883	Approved
0.6545	Remote Similarity	NPD7102	Approved
0.6545	Remote Similarity	NPD7290	Approved
0.6538	Remote Similarity	NPD5696	Approved
0.6522	Remote Similarity	NPD6116	Phase 1
0.6517	Remote Similarity	NPD5777	Approved
0.6514	Remote Similarity	NPD7320	Approved
0.6505	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6505	Remote Similarity	NPD5222	Approved
0.6505	Remote Similarity	NPD5221	Approved
0.6505	Remote Similarity	NPD4697	Phase 3
0.65	Remote Similarity	NPD5207	Approved
0.6491	Remote Similarity	NPD6009	Approved
0.6486	Remote Similarity	NPD8130	Phase 1
0.6486	Remote Similarity	NPD6847	Approved
0.6486	Remote Similarity	NPD6869	Approved
0.6486	Remote Similarity	NPD6617	Approved
0.6471	Remote Similarity	NPD7507	Approved
0.6466	Remote Similarity	NPD6319	Approved
0.6465	Remote Similarity	NPD5208	Approved
0.6458	Remote Similarity	NPD4788	Approved
0.6455	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6442	Remote Similarity	NPD6084	Phase 2
0.6442	Remote Similarity	NPD5173	Approved
0.6442	Remote Similarity	NPD6083	Phase 2
0.6429	Remote Similarity	NPD6098	Approved
0.6429	Remote Similarity	NPD8297	Approved
0.6429	Remote Similarity	NPD6882	Approved
0.6429	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.641	Remote Similarity	NPD5983	Phase 2
0.6408	Remote Similarity	NPD5695	Phase 3
0.6392	Remote Similarity	NPD3666	Approved
0.6392	Remote Similarity	NPD3665	Phase 1
0.6392	Remote Similarity	NPD3133	Approved
0.6387	Remote Similarity	NPD7492	Approved
0.6374	Remote Similarity	NPD6113	Clinical (unspecified phase)
0.6373	Remote Similarity	NPD5778	Approved
0.6373	Remote Similarity	NPD5779	Approved
0.6373	Remote Similarity	NPD4202	Approved
0.6355	Remote Similarity	NPD5211	Phase 2
0.6339	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6337	Remote Similarity	NPD46	Approved
0.6337	Remote Similarity	NPD5785	Approved
0.6337	Remote Similarity	NPD6698	Approved
0.6337	Remote Similarity	NPD5692	Phase 3
0.6333	Remote Similarity	NPD6616	Approved
0.6325	Remote Similarity	NPD6054	Approved
0.6321	Remote Similarity	NPD4696	Approved
0.6321	Remote Similarity	NPD5286	Approved
0.6321	Remote Similarity	NPD5285	Approved
0.6321	Remote Similarity	NPD6648	Approved
0.6316	Remote Similarity	NPD4695	Discontinued
0.6311	Remote Similarity	NPD7319	Approved
0.6311	Remote Similarity	NPD5282	Discontinued
0.6304	Remote Similarity	NPD3703	Phase 2
0.6304	Remote Similarity	NPD8039	Approved
0.6303	Remote Similarity	NPD7604	Phase 2
0.6286	Remote Similarity	NPD4755	Approved
0.6283	Remote Similarity	NPD6053	Discontinued
0.6281	Remote Similarity	NPD7078	Approved
0.6275	Remote Similarity	NPD7637	Suspended
0.6275	Remote Similarity	NPD6411	Approved
0.6275	Remote Similarity	NPD5694	Approved
0.6275	Remote Similarity	NPD6050	Approved
0.6273	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6273	Remote Similarity	NPD6412	Phase 2
0.6271	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.6271	Remote Similarity	NPD6016	Approved
0.6271	Remote Similarity	NPD6015	Approved
0.6271	Remote Similarity	NPD6921	Approved
0.6262	Remote Similarity	NPD5344	Discontinued
0.6262	Remote Similarity	NPD5223	Approved
0.6261	Remote Similarity	NPD6274	Approved
0.6261	Remote Similarity	NPD6868	Approved
0.625	Remote Similarity	NPD6371	Approved
0.6239	Remote Similarity	NPD5141	Approved
0.623	Remote Similarity	NPD7736	Approved
0.6218	Remote Similarity	NPD6370	Approved
0.6218	Remote Similarity	NPD5988	Approved
0.6207	Remote Similarity	NPD6317	Approved
0.6207	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6204	Remote Similarity	NPD4633	Approved
0.6204	Remote Similarity	NPD5224	Approved
0.6204	Remote Similarity	NPD5226	Approved
0.6204	Remote Similarity	NPD5225	Approved
0.6198	Remote Similarity	NPD6336	Discontinued
0.619	Remote Similarity	NPD5349	Clinical (unspecified phase)
0.6186	Remote Similarity	NPD6059	Approved
0.6186	Remote Similarity	NPD5209	Approved
0.6168	Remote Similarity	NPD4700	Approved
0.6167	Remote Similarity	NPD8328	Phase 3
0.6154	Remote Similarity	NPD6313	Approved
0.6154	Remote Similarity	NPD7327	Approved
0.6154	Remote Similarity	NPD6314	Approved
0.6154	Remote Similarity	NPD6335	Approved
0.6154	Remote Similarity	NPD7328	Approved
0.6148	Remote Similarity	NPD8293	Discontinued
0.6147	Remote Similarity	NPD5175	Approved
0.6147	Remote Similarity	NPD5174	Approved
0.6147	Remote Similarity	NPD6052	Approved
0.6134	Remote Similarity	NPD8033	Approved
0.6129	Remote Similarity	NPD3702	Approved
0.6117	Remote Similarity	NPD5281	Approved
0.6117	Remote Similarity	NPD5284	Approved
0.6111	Remote Similarity	NPD3700	Clinical (unspecified phase)
0.6111	Remote Similarity	NPD3699	Clinical (unspecified phase)
0.6106	Remote Similarity	NPD4634	Approved
0.6102	Remote Similarity	NPD7100	Approved
0.6102	Remote Similarity	NPD7516	Approved
0.6102	Remote Similarity	NPD7101	Approved
0.6095	Remote Similarity	NPD5210	Approved
0.6095	Remote Similarity	NPD4629	Approved
0.6082	Remote Similarity	NPD1780	Approved
0.6082	Remote Similarity	NPD1779	Approved
0.608	Remote Similarity	NPD7260	Phase 2
0.6078	Remote Similarity	NPD4753	Phase 2
0.6078	Remote Similarity	NPD6101	Approved
0.6078	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6078	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.605	Remote Similarity	NPD8294	Approved
0.605	Remote Similarity	NPD8377	Approved
0.6044	Remote Similarity	NPD4691	Approved
0.6038	Remote Similarity	NPD7732	Phase 3
0.6033	Remote Similarity	NPD6067	Discontinued
0.6032	Remote Similarity	NPD6845	Suspended
0.602	Remote Similarity	NPD4223	Phase 3
0.602	Remote Similarity	NPD4221	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